X-RAY STRUCTURAL STUDIES OF SOME GROUP VIII
COMPOUNDS WITH CATALYTIC IMPLICATIONS
By
DOUGLAS ALLEN SULLIVAN
A DISSERTATION PRESENTED TO THE GRADUATE
COUNCIL OF THE UNIVERSITY OF FLORIDA
IN PARTIAL FULFILLMENT OF THE REQUIREMENTS FOR
THE DEGREE OF DOCTOR OF PHILOSOPHY
UNIVERSITY OF FLORIDA
1975
To Jeanie
ACKNOWLEDGEMErJTS
I sincerely thank Dr. Gus J. Palenik for his enthusi-
astic guidance throughout this work. I am deeply apprecia-
tive of the advice and instruction concerning crystallo-
graphic techniques given by Dr. M. Mathew and of the diligent
synthetic work of Ruth C. Palenik. I wish to thank Dr.
Marvin Rausch for providing excellent samples of metallo-
cycle compounds. I am indebted to the chemistry faculties
of Marshall University and the University of Florida for
their apt instruction. I would like to especially thank the
other members of the Center for Molecular Structure for
their thoughtful suggestions and discussions. The typing
expertise of Ann Kennedy is evident in this, perhaps her
last, crystallographic dissertation. Lyle Plymale and Don
Herbert are acknowledged for their inspirational teaching
during my formative years. I would like to express my
appreciation to my parents, Mr. and Mrs. I. O. Sullivan, for
their support and encouragement throughout my formal educa-
tion. Finally, I thank my wife, Jeanie, and my son, David,
for their love and devoted understanding.
Ill
Table of Contents
ACKNOWLEDGEMENTS
LIST OF TABLES
LIST OF FIGURES
KEY TO ABBREVIATIONS
ABSTRACT
CHAPTER 1:
CHAPTER 2:
CHAPTER 3:
CHAPTER 4:
CHAPTER 5
CHAPTER 6
CHAPTER 7:
INTRODUCTION
SYNTHESES AND CHARACTERIZATION
X-RAY DIFFRACTION EXPERIMENTAL
AN INVESTIGATION OF LIGAND- INDUCED
PROTON SHIFT: THE CRYSTAL AND
MOLECULAR STRUCTURES OF TRANS-
CHLORO (DIMETHYLGLYOXIMATO) (DIMETHYL-
GLYOXIME) (4-CHLOROANILINE) COBALT (III)
DIHYDRATE, TRANS-CHLOROBIS (DIPHENYL-
GLY0XIJ4AT0) ( 4-CHLOROANILINE) COBALT ( III)
ETHANOLATE, AND TRANS-B IS (DIMETHYL-
GLYOXIMATO) BIS (4-CHLOROANILINE) COBALT
(III) CHLORIDE
A NOVEL BINUCLEATING LIGAND: THE
CRYSTAL AND MOLECULAR STRUCTURES OF
1,4-DIHYDPJ^ZINOPHTHALAZINEBIS (2-PYRI-
DINIUMCARBOXALDIMINE) NITRATE DIHYDRATE
AND y-CHLOROTETRAAQUA [1 , 4-DIHYDRAZINO-
PHTHALAZINE3IS ( 2-PYRIDINECARBOXALDIMINE) ]
DINICKEL(II) CHLORIDE DIHYDRATE
MODELS OF PROPOSED INTERMEDIATES FOR
THE CATALYZED CYCLIZATION OF ACETYLENES:
THE CRYSTAL AND MOLECULAR STRUCTURES OF
1- (tt-CYCLOPENTADIENYL) -1-TRIPHENYLPHOS-
PHINE-2, 3,4,5-TETRAKIS (PENTAFLUOROPHENYL)
COBALTOLE and 1- (tt-CYCLOPENTADIENYL) -1-
TRIPHENYLPHOSPHINE-2 ,3,4, 5-TETPAKIS
(PENTAFLUOROPHENYL) RHODOLE
CONCLUDING REM^FJCS
111
vi
ix
X
xi
1
4
17
30
83
114
141
IV
APPENDIX A: BOOTHITl 144
APPENDIX B: OBSERVED AND CALCULATED STRUCTURE FACTORS 154
REFERENCES 230
BIOGRAPHICAL SKETCH 237
LIST OF TABLES
Table 1.
Table 2.
Table 3.
Table 4.
Table 5.
Table 6.
Table 7.
Table 8.
Table 9.
Table 10.
Table 11.
Table 12.
Table 13.
Table 14.
Table 15.
Table 16.
Elemental Analysis
Infrared Spectra
Ultraviolet Spectra
Crystallographic Data
Schemes of Refinement
Final Atomic Parameters of
Nonhydrogen Atoms for
C£Co{H2dmg) (dmg) (clan)
Final Parameters for the
Hydrogen Atoms for
C£Co(n2dmg) (dmg) (clan)
Final Atomic Parameters for
the Nonhydrogen Attorns of
C'tCo(H2dpg2) (clan)
Final Parameters for
Hydrogen Atoms for
C£Co(H2dpg2) (clan)
Final Atomic Parameters for
Nonhydrogen Atoms of
[Co(Hdmg) 2 (clan) 2]C-e
Final Pararaeters for
Hydrogen Atoms for
[Co(Hdmg) 2 (clan) 2]C£
Selected Interatomic Distances
in Some Cobaloxime Complexes
Selected Interatomic Angles
in Some Cobaloxime Complexes
Deviations and
Selected Lcast-
in C£Co(H2dmg) (
Deviations and
Selected Least-
in C£Co(H2dpg2)
Deviations and
Selected Least-
in [Co (Hdmg) ~ (c
Equations of
Squares Planes
dmg) (clan)
Equations of
Squares Planes
(clan)
Equations of
Squares Planes
Ian) 2]C£
8
10
15
18
28
33
35
37
41
43
45
52
54
59
61
63
vx
Table 17.
Table 18.
Hydrogen Bonds in Cobaloximes
Dihedral Angles Formed by
Selected Planes in Some
Cobaloxime Complexes
Table 19. A Summary of the Average Bond
Distances in XYCo(H2dmg2)
Complexes
Bond Distances and Bond Angles
of Coordinated 4-Chloroaniline
Molecules
Bond Distances, Bond Angles, and
Least-Squares Planes of Phenyl
Rings in C£Co (H2dpg2) (clan)
Final Atomic Parameters of
Nonhydrogen Atoms for
H2dhphpy(N03)2'^H20
Final Parameters for the
Hydrogen Atoms in
H2dhphpy(N03)2-2H20
Final Atomic Parameters of
Nonhydrogen Atoms for
[Ni2C£ {H2O) 4 (dhphpy) I Cl^ • 2H2O
Final Parameters for the
Hydrogen Atoms in
[HiyCl (H2O) 4 (dhphpy) ] Cl^ ' 2H2O
Selected Interatomic Distances
for H2dhphpy(N03) 2-2H20 and
[Ni2C£ {H2O) 4 (dhphpy) ] Cl^ ' 2H2O
Selected Angles in
H2dhphpy(N02)2'2H20
Table 20.
Table 21.
Table 22.
Table 23.
Table 24.
Table 25.
Table 26.
Table 27.
Table 28.
Table 29.
Table 30.
2H2O
Selected Angles in
[Ni2C£ (H2O) 4 (dhphpy) ] Cl^
Hydrogen Bonds in
Hodhphpy(N03) 2-2H20 and
[Ni2C£ (H2O) ^ (dhphpy) ] Cl^ • 2H2O
Deviations and Equations of
Selected Least-Squares Planes
in H2dhphpy (N03)2-2H20 and
[Ui^Cl (HO) 4 (dhphpy) ] Cl^ • 2H2O
64
73
77
80
81
85
86
88
92
98
100
101
103
109
Vll
Table 31
Table 32.
Table 33
Table 34
Table 35.
Table 36
Table 37
Table 38
Table B-1.
Table B-3
Table B-4
Table B-5,
Final Atomic Parameters for the
Nonhydrogen Atoms in
C4 (fph) 4C0 (cp) (tpp) and
C4(fph)4Rh(cp) (tpp)
Selected Bond Distances of
C^(fph)^M(cp) (tpp)
Selected Bond Angles of
C^(fph)^M(cp) (tpp)
Deviation from and Equations
of Some Least-Squares Planes
of C4 (fph) 4Co(cp) (tpp) and
C4(fph)^Rh(cp) (tpp)
Average C-F and C-C Distances
for the Pentaf luorophenyl
Groups in C^ (f ph) ^M (cp) (tpp)
Bond Distances and Bond Angles
of Pentaf luorophei^iyl Groups
in C^(fph)^Co(cp) (tpp)
Bond Distances and Bond Angles
of Pentaf luorop};.enyl Groups
in C^ {fph)^Rh(cp) (tpp)
Bond Distances and Bond Angles
of Triphenylphosphine in
C^(fph)^M(cp) (tpp)
Observed and Calculated Structure
Factors for C£Co (H^dpg^) (clan)
119
Table B-2. Observed and Calculated Structure
Factors for [Co(Hdrag) (clan) ]C£
Observed and Calculated Structure
Factors for H-dhphpy (NO^) „ • 2H 0
Observed and Calculated Structure
Factors for [Ni„C£ (H^O) . (dhphpy) ] -
C£2*2H20 ^
Observed and Calculated Structure
Factors for C , (f ph) .Rh (cp) (tpp)
128
129
130
133
134
136
138
156
173
181
190
205
vixi
LIST OF FIGURES
Figure 1. An ORTEP drawing of 47
C£Co(H2dmg) (dmg) (clan) •2H2O
Figure 2. An ORTEP drawing of 49
C£Co(H2dpg2) (clan) •C2H3OH
r: 51
Figure 3. " An ORTEP drawing of
[Co (Hdmg) 2 (clan) 2KC
Figure 4. A projected view along Co-N(l) 70
for CCCo(H2dmg) (dmg) (clan)
Figure 5. A projected view along Co-N(l) 72
for (a) [Co(ndrag)2(clan) 2]C£
and (b) CCCo (H2dpg2) (clan)
Figure 6. An ORTEP drawing of
H2dhphpy (N03)2'H20
Figure 7. An ORTEP drawing of
[Ni2C^ (}l20) 4 (dhphpy) ]C£3- 2H2O
A packing diagram of 1^^
H2dhphpy (NO3) 2-2K20
Figure 8,
Figure 9. A packing diagram of
[Ni2C£ (II2O) 4 (dhphpy) ] 0^3 • 2H2O
Figure 10. An ORTEP drawing of
C4(fph)4Co(cp) (tpp)
95
97
108
126
IX
KEY TO ABBREVIATIONS
LIPS ligand-induced proton shift
H-dmg dimethylglyoxime
dmg dimethylglyoxime dianion
Hdmg ' dimethylglyoxime monoanion
Hpdmg- bis (dimethylglyoximate) with
relative proton positions
unspecified
sulfa sulfanilamide
dhph 1, 4-dihydrazinophthalazine
dhphpy 1, 4-dihydrazinophthalazinebis (2-
pyridinecarboxaldimine)
pyca 2-pyridinecarboxaldehyde
clan 4-chloroaniline
Hjdph diphenylglyoxime
Hjmpg methylphenylglyoxime
fph pentaf luorophenyl
cp cyclopentadienyl anion
tpp triphenylphosphine
an aniline
4-FPYTSC 4-formylpyridinethiosemicarbazone
Abstract of Dissertation Presented to the Graduate Council
of the University of Florida in Partial Fulfillment of the
Requirements for the Degree of Doctor of Philosophy
X-RAY STRUCTURAL STUDIES OF SOME GROUP VIII
COMPOUNDS WITH CATALYTIC IMPLICATIONS
By
Douglas Allen Sullivan
December, 19 75
Chairman: Gus J. Palenik
Major Department: Chemistry
X-ray structural investigations of compounds containing
Group VIII metal atoms are presented. The compounds studied
illustrate interatomic interactions which may be of impor-
tance in catalytic processes. The structures of metal-con-
taining compounds were solved by locating the heav;^' atoms
in Patterson functions and locating the remaining atoms in
Fourier syntheses. The direct method of symbolic addition
was used in the one, all light-atom case presented. Trial
structures were refined by the method of least-squares.
The crystal structure of trans-chloro (dimethylglyoxima-
to) (dimethylglyoxime) (4-chloroaniline) cobalt (III) illustrates
an unusual ligand-induced proton shift. Both neutral and
dianionic dimethylglyoxime groups are found in the complex
and the 4-chloroaniline ligand is oriented over the dianion-
ic dimethylglyoxime. The structure of trans-bis (dimethyl-
xi
glyoximato) bis (4-chloroaniline) cobalt (III) chloride shows
that complex to contain two monoatomic dimethylglyoxime
ligands and the 4-chloroaniline ligands to be skewed rela-
tive to the diglyoxime ligands. The crystal structure of
trans-chlorobis (diphenylglyoximato) {4-chloroaniline) cobalt-
(III) is described. Trends in the structures of these com-
pounds and in the previously reported structures of similar
compounds are discussed. Ultraviolet and infrared spectra
of these compounds are given.
The synthesis of a novel chelating ligand capable of
binding two metal ions is described. The characterizations,
including crystal structures, of its protonated forin, 1,4-
dihydrazinophthalazinebis (2-pyridiniuracarboxaldimine) nitrate
dihydrate, and of a nickel complex, y-chlorotetraaqua []. ,4-
dihydrazinophthalazinebis (2-pyridinecarboxaldimine) ]dinickel-
(II) chloride dihydrate, are presented. The planar ligand
is shown to bind tv/o nickel ions with a separation of 3. COS
o
(1) A. A chloride ion occupies a bridging site in the plane
of the nickel atoms and the ligand. The magnetic moment per
nickel atom of the chloride bridged complex was deteinnined
to be 2.74 B.M. at 40°C. The plausibility of structurally
similar complexes mimicking the nitrogen-fixing enzyme
nitrogenase is also discussed.
The X-ray crystal structures of 1- (ir-cyclopentadienyl) -
l-triphenylphosphine-2 ,3,4, 5-tetrakis (pentaf luorophenyl) co-
baltole and 1- (Tr-cyclopentadienyl) -1-triphenylphosphine-
2 ,3, 4 , 5-tetrakis (pentaf luorophenyl) rhodole are reported.
xii
These compounds are viewed as stabilized intermediates in
the catalyzed cyclization of acetylenes. In each case the
metal atom forms a metallocyclo by a-bonding to the ter-
minal carbons of a butadiene-like fragment. The ir-bonding
in the metallocycle appears to be dclocalized.
XI 11
CHAPTER 1
INTRODUCTION
Western civilization has demonstrated the efficiency-
oriented phenomenon of expending large amounts of energy to
find ways of requiring less human energy. This is evident in
the evolution from animal trails to freeways and from muscle
to sophisticated, high-energy machinery. On the molecular
scale the more efficient path io provided by catalysts. As
alchemists searched for the "philosopher's stone" many chemists
have been seeking catalysts. The application of catalysis is
now advancing through the development of an understanding of
the mechanisms of catalytic processes.
Life processes are dependent upon chemical reactions
controlled by enzymes. "It is not generally appreciated how
little is understood about the mechanisms by which enzymes
bring about their extraordinary and specific rate accelera-
tion." Investigation of enzymes should not only be fun-
damental in the understanding and maintenance of life pro-
cesses but also should contribute to developing more effi-
cient industrial processes.
Much of the investigation of enzymes has concerned the
use of model compounds. "Model building and the application
of material analogues are becoming increasingly important
for the elucidation of fundamental problems of biochemical
structure and reactivity."^ X-ray structural studies of
enzyme models are important for the exploration of structure-
activity relationships. Solid state studies of enzym- model
compounds are of particular relevance I ocauso of the high
degree of order the macromolecular enzymes themselves possess.
While electrostatic and hydrogen-bonding forces are
usually considered the major binding forces in enzyme-sub-
strate interactions, the strong charge-solvating and hydro-
gen-bonding ability of water tends to reduce the possibility
of obtaining large binding energies from these forces. To
explain the large binding energies found, "hydrophobic forces"
are presumed to exiso in these intermolecular interacions in
aqueous solution.^ The enthalpies of mixing of aromatic li-
quids with aliphatic liquids indicate that aromatic mole-
cules prefer an aromatic environment. ' "Stacking interac-
tions" involving the 7i-systems of aromatic groups within the
enzyme's protein structure may account for part of the "hydro-
phobic forces" and contribute to the orientation of the enzyme-
substrate interaction.^ The ligand-induced proton shift (LIPS)
observed in ClCoiU^dx^g) (dmg) (sulfa) [the key to abbreviations
is given on page xl is an indication of the importance of this
TT-type interaction. A further examination of LIPS v. as under-
taken and is presented in this work.
The design of enzyme models is often based on sparse
structural information about the prosthetic group of the en-
zyme. Efforts to miiTLic the nitrocen-f ixing enzyme nitrogenase
have been concerned with the metal to nitrogen bond. The
6 7
probable binuclear nature of the enzyme's active site ' has
largely been ignored. The structures of a novel binuclea-
ting ligand and its nickel (II) complex are presented here
as a first step in the construction of a new generation of
models for nitrogenase.
When the mechanism of a chemical process is believed
to be understood, stable compounds similar to the interme-
diates of the reaction may be prepared and examined to
support the proposed mechanism. One proposed mechanism for
the catalyzed cyclization of acetylenes v/ould have a five-
membered ring containing a metal atom and a cyclobutadiene
8— 1 3
fragment as one of the intermediates. The first struc-
ture of such a stabiliF.ed intermediate containing a cobalt
atom and the structure of the rhodiv;m analog are presented
in this study.
CHAPTER 2
SYNTHESIS AND CHARACTERIZATION
Synthesis
Crystals of all cobaloxime compounds were generously
provided by R. C. Palenik* and were used v.'ithout recrys-
tallization.
M. D. Rausch and R. H. Gastinger synthesized the
14 15
metallocycles containgmg cobalt and rhodium. They
supplied well-formed crystals of those metallocycles for
X-ray structural studies.
Unless otherwise indicated all solvents were reagent
grade and were used without further purification. All pre-
parations were carried out in air. All melting points were
taken on a Mel-temp apparatus in open capillaries and are
uncorrected.
16
The published method was used to prepare dhph for
succeeding experiments. To 6.40g (49.0 mmoles) 1,2-dicyano-
benzene (98%; Aldrich Chemical Corripany, Milwaukee, Wise.) in
12.5 ml 1,4-dioxane was added a mixture of 15.0 ml (ca. 250
mmoles) hydrazine hydrate (85%; Fisher Scientific Company,
Fair Lawn, N. Y.) and 4 . 0 ml glacial acetic acid (reagent;
Baker and Adamson, Morristown, N. J.). After being heated
*These complexes were prepared using standard procedures
with synthetic details to be published at a later date.
for three hours the mixture was cooled and the red product
was collected (yield, ca . 40%). The decomposition temper-
ature of 193 °C was in agreement with the reported value.
A solution of 0.0955g (0.50 mmoles) of the previously
prepared dhph in 4 0 ml absolute ethanol was added to a solu-
tion of 0.237g (1.0 mmoles) UiCl2' ^^2^ (reagent; Matheson,
Coleman and Bell, Norwood, Ohio) and 0.095 ml (0.99 mmoles)
pyca (99%; Aldrich) in 40 ml absolute ethanol. Upon slow,
almost complete, evaporation in air of that solution olive
green crystals of [Ni2C£. (H2O) ^ (dhphpy) ] 0^3 • 2H2O formed.
Analogous procedures were carried out replacing NiC£2 *
H2O with CoCl2'^^-2^' CuC£2 '2^120 (reagent; Fisher), ZnCl2
(reagent; Mallinckrodt Chemical Works, St. Louis, Mo.) and
FeC£2'4^2^ (reagent; r4atheson, Coleman and Bell) without
success in obtaining a crystalline product. Similar pro-
cedures were followed with the addition of ca. 0.2 ml of
12 M hydrochloric acid (reagent, 38%; Baker and Adamson) to
solutions of CuC£2'2H20 and FeCc2'4H20. Again, no suitable
products were formed. Attempts to separate and recrystallize
reaction products from water, water-ethanol , methanol and
pyridine failed to give a crystalline product. V7hen CuC£2
was present, gas evolved from the reaction mixture.
Additional attempts wore made to isolate complexes
similar to {Ni C(l (H 0) (dhphpy) ] Ci^ using dhph obtained by
recrystallization from hot water of H2dhphS0^ (ICN-K and K
Laboratories, Ir>.c. , Plainviev/, N. Y.) to which an equivalent
amount of KOH (certified A.C.S.; Fisher) had been added.
Those attempts were unsuccessful.
The red-orange plates of H2dhphpy (NO^) 2^ 2H2O used in
crystallographic studies had been recrystallized from water.
The crude product formed upon cooling a solution made by
adding 0.190g (1.0 mmole) dhph in 20 ml warm water to a
solution containing 0.583g (2.0 mmoles) Ni (NO-^) 2 ' ^H^O (re-
agent; Mallinckrodt) and 0.8 9 ml (9.4 mmoles) pyca in 10 ml
warm water followed by drop-wise addition of nitric acid
(reagent, 71%; Baker and Adamson) to a pH less than 1.
Also, H^dhphpy (NO^) 2 was prepared by first adding 1.90
ml (20.0 miaoles) pyca to a suspension of 2.878g (10.0 mmoles)
H2dhphS0. in 100 ml water. A brick-red solid formed upon
addition of l.llg (ca. 17 mmoles) KOH. After washing with
water and drying in air, the brick-red solid was suspended
in 100 ml of 95% ethanol and 1.30 ml (21 mmoles) of nitric
acid were added. Small red-orange needles of H2dhphpy (NO^) 2
which decompose at 126°C were filtered, v;ashed with ethanol,
and then ether and air dried (yield 4.0g, 75%).
Freshly prepared hydrated metal hydroxides were reacted
with H2dhphpy (NO^) 2 in methanol. Each of the metal hydroxides
was filtered after adding 1 M KOH to aqueous solutions of
Ni(N02)2-6H20, Cu (NO^) 2 ' 3H2O (reagent; J. T. Baker Chemical
Company, Phillipsburg, N. J.), Fe (C^O^) 2 • 6H2O (reagent; G.
Frederick Smith Chemical Company, Columbus, Ohio) and
Zn(NO,)2-6H 0 (reagent; Matheson, Coleman and Bell). After
the reaction mixtures were stirred until there was no further
change in color, they were filtered and the filtrates were
allowed to evaporate. Only the reaction with nickel (II)
hydroxide produced a crystalline product. Attempts to re-
crystallize that maroon product from methanol, ethanol,
ethanol-water, and 2-propanol did not yield crystals suitable
for crystallographic studies.
Discussion of Characterization
The microananlyses recorded in Table 1 were performed
by Galbraith Laboratories, Inc., Knoxville, Tennessee, for
the dhphpy compounds and by Atlantic Microlab, Inc., Atlanta,
Georgia, for the cobaloxime complexes. The calculated per-
centages of carbon, hydrogen, and nitrogen for the dhphpy
compounds correlate well with the measured percentage. Two
water molecules per molecule of dhphpy in each are indicated
by the elemental analysis. This is confirmed in the struc-
tural determination. Similarly, the eleraental analysis of
C-tCoCH^dmg) (4-nitroaniline) is in agreement with the expected
formula with tv;o water molecules present. Based on the
measured density and crystallographic data the molecular
weight of [Co (H2dmg2) (4-methylaniline) ] c£ should be 596.
This is greater than its formula weight of 538.9 and the
presence of molecules of solvation is expected. Three water
molecules or one molecule of the ethanol solvent per formula
could account for the difference. Neither of these possi-
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bilities is confirmed by the CHN analysis (see Table 1) .
IR spectra of samples as mineral oil mulls between
polished plates of fused sodium chloride were recorded on a
Beckraan Model IRIO grating spectrophotometer from 4000 to
500 cm" . The spectra were calibrated using the 1601.0 cm
absorption of a polystyrene film. IR spectra of selected
compounds are reported in Table 2. The IR spectra of the
bis (diglyoxime) cobalt (III) complexes with aniline derivatives
exhibit many features of similar cobalt complexes with nit-
, 18
riles and isonitriles described by Batyr et al. The
18
spectra of the cobaloximes shov; the absorption assigned to
the C=N stretch between 15 50 cm" and 158 0 cm . The ab-
18 -1
sorptions associated with the N-0 band at ca. 124 5 cm
and ca. 1095 cm" are present also. A weak absorption in
the 1700-1800 cm" range appears in some of the spectra but
with lov/ resolution. Peaks in this region have been
assigned to the 0---H-0 bridge between the dioximate
ligands. The presence of a symmetrical bridge has been
20
suggested to rationalize this low frequency.
Absorption spectra in the ultraviolet region were re-
corded on a Gary Model 15 spectrophotometer. Spectra of
solutions were measured from 26.7 kK (375 my) to 47.6 kK
(210 my) using the double beam method with the pure solvent
as the reference. Solutions of the cobaloxime complexes in
methanol (spectroquality ; Matheson, Coleman and Bell) and
solutions of the diiphpy compounds in 0.1 M hydrochloric
10
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14
acid were used. The UV spectra are reported in Table 3.
The UV spectra of all these compounds are dominated by
21
intense charge transfer bands. Yamano et al. report thrde
bands in this region for compounds of the formula [Co(H2dmg2)-
A ] where A is an aniline derivative. These three bands are
present in [Co (Hdmg) 2 (clan) 2] C-t and [Co (H2dmg2) (4-methyl-
aniline)2]C£. The band between 25.0 and 27.5 kK (400 to 360
my) was assigned^-*- to the charge transfer from the aniline
ligand to the cobalt ion. In agreem.ent with this assignment
the band for the complex of the more basic 4-methylanJ line
at 27.6 kK is lower in frequency than that for the analogous
complex of clan at 28.9 kK. The band near 33.0 kK (300 my)
was assigned^ ■"" to the charge transfer from the cobalt ion to
the dioximate ligand. The band near 40.0 kK (250 my) was
assigned'*'"'" to the intra-Hdmg tt-^-it* transition.
The UV spectra of cobaloxime complexes with a cliloride
ligand trans to a substituted aniline shov/ three bands, also.
One band is between 27.0 and 33.0 kK (370 to 300 my). The
other bands lie near 39.0 kK (255 my) and 43.0 kK (230 my).
No assignments have been made for these three bands.
The charge transfer spectrum of a solution of [Ni2Ct-
(H-0) . (dhphpy)]C£-. •2H 0 in 0.1 M HCl exhibits the same ab-
sorptions as that of a solution of H2dhphpy (N02)2 ^^ 0-^ ^
HCl. The intense bands at 25.4, 32.7, and 37.3 kK (395, 305,
and 268 my) are presumably due to the aromatic system of the
ligand.
15
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16
The magnetic moment per nickel atom of (Ni„C-£ (H^O) -
{dhphpy)]Cf was determined to bo 2.74 D.M. at 40''C. Data
22 23
for this calculation ' were obtained using a Varian A-60A
Analytical NMR Spectrometer and aqueous solutions containing
2% by volume t-butanol as the indicator. This magnetic
moment is in agreement with those of binuclear complexes of
24
nickel reported by Ball and Blake. Their complexes of the
general formula [Ni (dhph) ] _X . 'nll^O (X = Cl, Br, or I) had
room temperature effective magnetic moments ranging from
2.79 to 2.89 B.M. As in the case of [Ni (dhph) ] 2X . •nH20,
2+
where two Ni ions are bridged by a conjugated system,
spin-spin interaction is indicated in [Ni„C^ (H^O) - (dhphpy) ] -
CHAPTER 3
X-RAY DIFFRACTION EXPERIMENTAL
Except where noted in the text, the experimental methods
described in this section were used in preliminary crystallo-
graphic examination, collection and processing of data, and
refinement of trial structures.
Data obtained using precession and Weissenberg X-ray
25-27
photographic techniques were used m determining the
preliminary space groups and cell constants. After centering
fifteen intense reflections d.a computer-controlled Syntex
pT dif fractometer and selecting an indexing consistent with
preliminary photographs, accurate call constants with esti-
mated standaxd deviations vere obtained from least-squares
fittings of 2G, J?,x / and 0 f or those reflections. In each
case the orientation matrix for data collection and the unit
cell volume with its standard deviation were derived from
these data. The calculated density was in agreement with
28
the density measured by the flotation method except in the
cases of the metal-containing heterocycles. The specific
gravity of the flotation liquid was measured to ±0.01 with
a precision hydrometer. Relevant crystallographic data for
each of the compounds studied are given in Table 4.
The suitability of a crystal for data collection was
determined by its physical shape and size, the ease v;ith
17
10
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22
which the reflections wore centered on the diffractometer ,
and the values of the refined cell constants with their
estimated standard deviations compared to the cell constants
obtained by photographic methods. All intensity measure-
ments v;ere made with a fyntex PI diffractometer at ambient
temperature. All unique refelctions up to a limiting 26
value were measured using a variable speed 0-20 scan tech-
nique. The scan rate was determined from a fast throe-
second counting scan of the reflection peak and varied lin-
early from l°/rainute for counting rates of 150.0 c/scc. or
less to 24 "/minute for 1500.0 c/sec. or more. The intensity,
1/ was defined:
T / 4. \ r /i. J. T ^ \ {bac):ground counts) ,
I=(scan rate) total scan counts)— ,r: — -, j j. /— ;] .
(background to scan rate)
Peaks were scanned from 1'^ below Ka, to 1° above Ka„. Mea-
surements of the background count were made at the limits of
each scan. The estiraatod standard deviation, o(I), of each
reflection was taken to be:
„fT\-r f4.^*.-.-\ ^ J- \ , (background counts) i 1/2
a(I) = l (total scan counts) + ,r-'T -"j-z r-- — r^ J
(background to scan ratio) •^
For molybdenum radiation, the incident beam was monochro-
matized by a low order reflection of graphite. Any changes
in the system were detected by measuring four standard re-
flections after each 96 intensity measurements.
A standardized data set was obtained by scaling the
data to the initial value of the sum of the measured in-
tensities of the standard reflections. The scaled in-
23
tensities of duplicate or equivalent reflections were av-
eraged. Reflections with an intensity greater than Ka(I),
where K is given in Table 4, were considered reliable. The
unreliable reflections with I<Ka(I) were identified by a
minus sign and not included in further steps of the struc-
ture solution. Corrections for Lorentz-polarization were
of the forcv:
1 _ sin 26 . ■
Lp (l+cos^28)
To obtain a set of observed structure factors, ^obs '^'
the monochrciriator wao also assumed to be 50% perfect crystal
and 50% mosaic crystal.
Scattering factors v/ere obtained from Hanson, Herman,
29 3 0
Lea, and Skillman; Stewart, Davidson, and Simpson; Doyle
and Turner; and are uncorrected for anomalous dispersion.
The natural log of the scale factor and the overall temper-
32
ature factor were initially estimated from a V7ilson pilot.
The initial choice of a centric or acentric space group was
33
made on the basis of calculated intensity statistics.
In the case where molecules contained at least one heavy
atom (Atomic Number -^ 16) the approximate positional co-
^ • 3 4 ^
ordinates were determined using a Patterson function of
the form:
P(UW7) =- Z Z E |F(hkl) l^cos27r{hU+kV+lW) .
h=-°° k^-"- l=-<»
Using the location of the heavy atom(s) in a structure
24
factor calculation allowed a sufficient number of reflection
phases, a(hkl)'s, to be assigned. The magnitude of the
structure factor, | F^^,^ |, and the phase may be defined by
27
the following equations:
A^, , = Ef . cos 2TT(hx. + hy. + Iz.)
hkl .J 3 D 3
B , , = If. sin 27r(hx. + hy . + Iz )
where f . is the scattering factor for atom j.
Additional atomic positions could then be determined
through the use of Fourier syntheses of the form:
OO 00 CO
(XYZ) =- E Z Z l^hkl' ^°^ 2tt[ (hX+kY+lZ)-a^j^^] .
V h = 0 k=-<» l^-o)
The positional coordinates of atoms in the trial structure
were estimated froir. the Fourier generated electron density
map using a FORTRAN computer program, BOOTHITl, written in
the course of this work. A description and listing of
BOOTHITl is contained in Appendix A. Alternate structure
factor calculations and Fourier syntheses were repeated
until all nonhydrogen atoms were located.
In the case of a compound not containing a heavy atom
but having a centrosymmetric space group, the direct method
of symbolic addition was used. The FORTRAN computer programs,
FAKE-MAGIC-LINK-SYMPL, developed by E. B. Fleischer, R. B.
25
K. Dewar, and A.L, Stone ' were used to generate possible
solutions to the phase problem. The programs first converted
If , I's to normalized structure factors, E's, through the
' obs '
definitions:
fp )2 ^ J^ I ,2 (T sin G)/X
^ absolute^ ^2 'obs'
and
2 2^2
absolute . i
where the scale factor, K, and the overall temperature fac-
tor, T, were generated by a Wilson plot; where e was a
symmetry factor applied to reflections in special zones; and
where f.'s were the scattering factors for N atoms. The pro-
grams then assigned symbols representing the phases to six
of the largest E's having the greatest number of interactions,
i.e., for E^ aiid E there exists E, . For such reflections
' h n. h-m
the probability, p, the.t the phase of E, is the same as
N
E (E E, ) is given by:
m h-m ^ -^
m=0
p = 0.5 + 0.5 tanh (-^-lE^i! ^ ^ E^-n,!)
a » 1 . 5 m=^ 0
where
N
^ j=l 3
with N being the number of atoms in the unit cell and Z. being
the atomic number of the j atom. The programs, when given
minimum acceptable probability criteria, iteratively assigned
relative signs to the phase symbols. Combinations of these
26
signed phase symbols were finally used in conjunction with
their structure factors to generate E-maps. The positional
coordinates of most nonhydrogen atoms were determined from
one of these E-maps. Structure factor calculations and
Fourier syntheses were used to refine the atomic positions
and, as in the heavy atom case, to locate any previously un-
found nonhydrogen atoms of the trial structure.
The trial structure was refined by least-squares
34
minimization of the function:
Residual =2w(l|F^^^| - If^^^^ID^
where
.ow
and
' obs ' ' low' ' obs ' ' 1<
' low' — ' obs' — ' high'
^^^ I^high!/l^obsl ^°^ l^obsl > l^high!
F, and F . , are constants given in Table 4. Prior to re-
low high
finement, an overall scale factor was chosen such that the
sum of F ^ equaled the sum of F , . Isotropic temperature
obs ^ calc
factors were used in the first three cycles of refinement
and then anisotropic temperature factors of the form:
exp[-(3j^^h^ + 622^^ ^ ^^33^^ '^ ^12^^ "^ ^13^^^ "^ B23h£)]
were used. The reliability index, R, was defined by:
K —
' obs
27
Calculations were performed on an IBM 370/165 computer
with programs written or modified by Dr. Gus J. Palenik,
except where previously noted. The refinement of each
structure is outlined in Table 5.
28
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U
CHAPTER 4
AN INVESTIGATION OF LIGAND-INDUCED PROTON SHIFT: THE CRYSTAL
AND MOLECULAR STRUCTURES OF TRANS-CHLORO (DIMETHYLGI.YOXIMATO) -
(DIMETHYLGLYOXIME) (4-CHLOROANILINE) COBALT ( III ) DIHYDRATE,
TRANS -CHLOROB IS (DIPHENYLGLYOXIMATO) ( 4-CnLOR07U\:iLINE) COBALT (HI)
ETHANOLATE, AND TRA_NS~BIS (DIMETHYLGLYOXIMATO) BIS (4-CHLO.HOANI-
LINE) COBALT (III) CHLORIDE.
The stability of bis (dimethylglyoxiine) metal coiriplexes
has long been known and their importance in both qualitative
37 3 8
and quantitative analysis has been widely recognized. '
Metal complexes of Hdmg have been used to study tlie trans-
39 40 41
effect and the trans- influence ' of various ligands in
octahedral complexes. Since the structural determination of
the B, „ coenzynie the trans-bis (dimethylglyoxime) cobalt com-
42-44 42
plexes have become of considerable interest. Schrauzer
has stated that to be capable of mimickiug P^ ^ ^ complex is
required only to have a cobalt ion in tiie presence of a strong-
binding planar ligand. Because Co(H„dmgp) complexes success-
fully mimic the reactions of a cobalt ion in the corrin ring
and because they are synthetically expedient, complexes of
Co(H»dmgp) have been investigated extensively in solution as
45
models for B, „ .
Until very recently there have been few structural data
on Co(Hpdmgp) complexes. ' ' Except for the work of
46
Palenik et al . no structural investigation has been made of
the interaction between the axial ligand and the equatorial
Hdmg ligands. This interaction may be of considerable con-
sequence.
30
31
Although sulfonamides are potent inhibitors of carbonic
anhydrase they do not form strong coordination bonds with
transition metal ions. Therefore, an interaction of the aro-
matic ring of the sulfonamide with the carbonic anhydrase pro-
53
tein has been proposed to make a large contribution to the
observed stability of the carbonic anhydrase-sulf onamide com-
plex. Since a cobalt atom can replace the zinc atom in car-
bonic anhydrase with only a 50% decrease in activity, complexes
of Co(H_dmg2) '^^Y pri.^ve to be useful models for investigating
the interaction of sulfonamides with carbonic anhydrase.
An apparent ligand-- induced proton shift (LIPS) was ob-
served in C-^Co (H2dmg2) (si.ilfa) which should be formulated
C-^Co (Kpdmg) <dmg) (sulfa) . To investigate further the LIPS
phenomena and to examine inter ligand interactions within this
type of complex the determination of the structures of C.£Co-
(H2dmg) (dmg) (clan) , [Co (Hdrag) 2 (clan) 2] C£, and C£Co (H2dmg2) ~
(clan) was undertaken.
Structure Solution and Refinem.ont
for C£Co(H2dmg) (dmg) (clan) '2lIoO
The heavy atom method was used with the positions of the
cobalt atom and of the ionic chloride ligand estimated from
a sharpened Patterson function. The magnitude of the Patter-
son function for the Co to C£ vectors was of the same order
as that for the Co to Co vector. The positions of the heavy
atoms, therefore, appeared ambiguous and several combinations
were used in Fourier syntheses to determine their actual lo-
32
cations, successive Fourier syntheses then revealed the loca-
tions of all nonhydrogen atoms in the compound. Three cycles
of full-matrix least-squares refinement with individual iso-
tropic thermal parameters and then three cycles of least-
squares refinement using. the block approximation with indi-
vidual anisotropic thermal parameters reduced R to 0.066. A
difference Fourier synthesis then indicated the absence of
additional nonhydrogen atoms and revealed the positions of
all hydrogen atoms. An outline of the refinement is given in
Table 5. The refinement was terminated after the parameter
shifts for the nonhydrogen atoms were less than one-tenth of
their corresponding estimated standard deviations.
The scattering factors for cobalt, chlorine, oxygen,
nitrogen, and carbon were from Hanson et al.^^ while those
for hydrogen were from StewarL e.L_al.-° A list of the observed
and calculated structure factors has been published and is
available.'''^ The final positional and thermal parameters are
given in Tables 6 and 7.
Structure Solution and Refinement
for C^Codl^dpg-;,) (clan) -C^H^OH
The nonstandard space group P2j^/n was chosen since the
standard P23,/c space group would require a very large value
for B. The position of the cobalt atom was estimated from a
sharpened Patterson function. The location of atoms and the
refinement proceeded as in the case of c£Co {Il2dmg) (dmg) (clan) •
2H2O. Two atoms, 0(S1) and C(Si), of an apparent solvent mole-
33
Table 6
Final Atomic Parameters of Nonhydrogen Atoms for c£Co(H2dmg)-
(drag) (clan)^
Atom
X
y
z
^11
^22
Co
19148(12)
36142(8)
21611(6)
1237(16)
4 54(7)
C£{1)
-1353 (2)
2445(1)
1882(1)
148(3)
65(2)
Cl{2)
8142(4)
10300(2)
3785(2)
512(9)
67(2)
0(11)
1633(7)
4573(4)
534(3)
305(13)
95(5)
0(12)
1742(6)
4621(4)
4260(3)
304 (13)
89(5)
0(21)
2285(7)
2611(4)
3796(3)
314(13)
104(5)
0(22)
1944(7)
2468(4)
17(3)
298 (13)
114 (6)
N(l)
4821(7)
4589 (5)
2375(3)
157(12)
93(6)
N(ll)
1600(7)
4753(5)
1536(3)
179(12)
75(6)
N(12)
1693(7)
4792(4)
3347 (3)
155(12)
58(5)
N(21)
2289(7)
2459(5)
2788(3)
191(13)
72(5)
N(22)
2144(7)
2398(5)
980(3)
158(12)
74(5)
C(ll)
1403(8)
5758(6)
2145(5)
170(15)
57(7)
C(12)
1443 (8)
5772(6)
3208(5)
158(15)
59(5)
C(13)
1247(10)
6794(6)
1785(5)
268(19)
85(8)
C(14)
1310(10)
6815(7)
4067(5)
281(20)
100(8)
C(21)
2584 (9)
1516(5)
2201(17)
214(17)
65(7)
C(22)
2509(9)
1475(6)
1124(5)
164(15)
65(7)
C(23)
3010(14)
584(8)
2593(7)
530(32)
112(10)
C(24)
2779(12)
465(7)
277(6)
410(27)
121(10)
C(l)
5676(7)
5999(5)
2722(4)
96(13)
70(5)
C(2)
6105(9)
6655(6)
3753(5)
198(15)
71(7)
C(3)
6866(9)
7971(6)
4082(5)
221(17)
91(8)
C(4)
7201(10)
3629(6)
3382(6)
195(17)
73(7)
C(5)
6809(10)
7972(7)
2340(5)
237 (19)
99(8)
C(6)
6047(9)
6644(6)
2005(5)
191(16)
82(7)
0(wl)
6682(7)
3785(5)
616(4)
264(13)
148(7)
0(w2)
6802(7)
3830(5)
3690(3)
275(13)
166(7)
a
All values are x 10^ except for Co which are x 10 . The
estimated standard deviations are given in parentheses, ine
temperature factors are of the form: exp [- ( ;<3_j_h^ + 822'"^' "^
34
Table 6 - extended
^33 ^12 ^13 ^23
276(4) 822(17) 219(13) 157(9)
53(1) 78(4) 25(3) 14(2)
138(2) 65(7) 46(7) 46(4)
36(3) 168(14) 7(9) 44(6)
32(3) 167(13) 70(9) 33(6)
41(3) 199(14) 74(10) 70(6)
30(3) 199(14) 31(9) ,25(6)
37(3) 123(14) 29(10) 50(7)
35(3) 108(14) 24(10) 26(7)
35(3) 71(13) 30(9) 19(6)
41(3) 123(14) 41(10) 39(7)
35(3) 99(13) 21(10) 12(7)
53(4) 101(17) 25(13) 41(9)
51(4) 73(16) 30(13) 14(8)
76(5) 190(21) -5(16) 55(10)
62(5) 214(22) 50(16) -6(10)
56(4) 134(18) 47(14) 44(9)
60(5) 110(17) 52(13) 24(9)
102(7) 347(31) 148(24) 106(14)
73(6) 301(28) 37(20) 11(12)
44(4) 72(15) 23(11) 44(8)
47(4) 89(17) 4(13) 28(9)
42(4) 95(19) 4(14) 8(9)
82(6) 61(18) 23(16) 39(10)
69(5) 99(20) 83(16) 95(11)
52(4) 104(18) 56(13) 52(9)
80(4) 241(16) 102(11) 100(8)
53(3) 295(16) 20(10) 22(7)
35
Table 7
Final Parameters for the-
(clan)^
Hyd
rogen
Atoms f(
or ClCodi
2 drag) (dmg)
Atom
[Bonded to]
Distance
X
y
z
B
H(B1) [0(22)
1 1.16(8)
153
(10)
335
(7)
17
'5)
6.3(1.8)
H(B2) [0(21)
I 1.13(8)
184
(10)
345
(7)
402
5)
6.7(1.8)
H(2) [C(2)]
0.89(5)
■591
(7)
621
(5)
420
4)
2.0(1.1)
H(3) [C(3)]
0.99(7)
726
(10)
858
(7)
4 78
5)
6.7(1.9)
H(5) [C(5)]
0.90(7)
709
(10)
838
(7)
187
5)
5.8(1.7)
H(6) [C(6)]
1.01(5)
558
(7)
609
(5)
127
4)
2.0(1.1)
H(7) [N(l)]
1.03(7)
522
(10)
434
(6)
16G
5)
6.1(1.7)
H(8) [N(l)]
0.83(6)
518
(9)
428
(6)
278
5)
4.5(1.5)
H(ll) [C(13)-
0.96(8)
243
(11)
753
(7)
212
6)
8.2(2.1)
H(12) [C(13)-
0.79(9)
37
(11)
692
(7)
203
6)
8.5(2.2)
H(13) [C(13)
1.00(1)
102
(10)
663
(7)
103
5)
7.1(1.9)
H(14) [C(14)
1.02 (7)
46
(9)
639
(6)
453
5)
5.8(1.7)
H(15) [C(14)
0.78 (7)
62
(9)
708
(6)
388
5)
4.9(1.5)
H(16) [C(14)
0.87 (8)
228
(11)
734
(8)
456
6)
8.6(2.2)
H(21) [C(23)
0.86(10)
414
(12)
59
(8)
248
6)
9.6(2.4)
H(22) [C(23)
0.92(9)
239
(12)
-21
(8)
211
6)
9.3(2.4)
H(23) [C(23)
0.97 (9)
266
(12)
52
(8)
3 26
7)
9.8 (2.5)
K(24) [C(24)-
1.03(9)
242
(12)
4 4
(8)
-46
V)
9.4(2.4)
H(25) [C(24)
0.84(10)
396
(12)
58
(8)
29(
6)
9.1(2.3)
H(26) [C(24)
1.00(7)
210
(10)
-38
(7)
40
5)
5.9(1.7)
H(wl) [0(wl)
0.70(8)
659
(11)
319
(7)
69
6)
7.2(2.0)
H(wl') [0(wl
I] 0.80(13)
771
(16)
438
(11)
72(
9)
15.2 (3.7)
H(w2) [0(w2)
0.79(7)
736
(10)
420
(7)
425(
5)
6.6(1.8)
H(w2') [0(v^2
] 0.71(7)
747
(10)
371
(6)
337 (
5)
6.0(1.8)
The hydrogen atom is given followed by the atcn to which it
is bonded in brackets, the corresponding bond distance (in A) ,
the positional parameters with estimated standard deviations
(x 10+3), and the isotropic thermal parameter (in A2) .
36
cu]c were located before refinement. The scheme of the refine-
ment is outlined in Table 5.
Although the compound was crystallized from ethanol,
difference I'ourier syntheses at various stages of refinement
failed to indicate the position of an additional atom in the
solvent molecule. Because a large region of relative high
electron density existing near C(fl) could be indicative of
an atom with high disorder and because ethanol v/as the sol-
vent, a molecule of ethanol was assumed to be present for the
purposes of determining the formula, molecular weight, and
density .
The cobalt, chlorine, oxygen, nitrogen, and carbon
29
scattering factors wore taken from Hanson e t a 1 . and those
for hydrogen from Stewart et al. Table B-1 is a list of
observed and calculated structure factors for C£Co (H2dpg2)~
(clan) . The final positional and thermal parameters are shov/n
in Tables 8 and 9.
Structure So lution and Refinement
for "ICo (Hdmg) 2 (clan) 2] C?.
With one molecule per unit cell in the centric PI space
group the cobalt atom and the chloride anion were required
to lie on centers of symmetry. The sharpened Patterson func-
tion was ill agreement with tlie chloride ion at 0--iO when the
cobalt atom is placed at 000. The remaining atoms were loca-
ted in a similar manner as in CgCo (H2dmg) (dmg) (clan) . An out-
line of the refinement is given in Table 5.
37
Table 8
The Final Atomic Parameters for the Nonhydrogen Atoms of ClCo
(H2dpg)2
(clan) a
Atom
X
Y
z
^11
^22
Co
3339(1)
3017(2)
2961(1)
33(1)
58(1)
Clil)
3101(2)
4797(3)
3049(2)
45(2)
68(3)
Cl{2)
6313(4)
60(5)
1153(3)
96(4)
151(6)
0(11)
3953(5)
3496(7)
1583(4)
47(5)
82(9)
0(12)
4349(5)
2916(10)
4348(4)
41(5)
210(13)
0(21)
2763(6)
2628(8)
4340(4)
54(5)
13 0(11)
0(22)
2334(5)
3078(8)
1587(4)
42(5)
102(9)
N(l)
3495(6)
14 61(9)
2903(6)
29(6)
97(12)
N(ll)
4172 (6)
3351(7)
2306(4)
41(6)
41(8)
N(12)
4368(7)
3168(9)
3660(5)
56(7)
78(11)
N(21)
2534 (7)
2738 (9)
3635(5)
50(6)
85(11)
N(22)
2312(6)
2882(9)
2294 (4)
39(6)
62(9)
C(ll)
4970(8)
3533(10)
2591(6)
24(7)
88(14)
C(12)
5080(8)
3361(11)
3373(6)
44(8)
101(15)
C(13)
5698(8)
3915(12)
2191(6)
38(8)
70(12)
C(14)
5956(9)
3431(11)
3862(7)
42(8)
82(14)
C(21)
1705 (S)
2557(10)
3364(6)
46 (8)
58(12)
C(22)
1575(7)
2672(10)
2562(5)
28(6)
66(12)
C(23)
1055(8)
2220(10)
3832(6)
54(8)
50(12)
C(24)
709(8)
2583(10)
2146(6)
52(8)
46(12)
C(l)
4167(8)
:048 (11)
2486(6)
54(9)
46(11)
C(2)
5012(9)
858(11)
2798(7)
65(10)
65(14)
C(3)
5687(9)
544(11)
2387 (8)
53(9)
62(13)
C(4)
5487(9)
448(11)
1654(8)
69(10)
53(13)
C(5)
4661(10)
592(13)
1341(7)
74(10)
123(18)
C(6)
3990(8)
883(11)
1733 (7)
45(8)
67(13)
C(1A)
5975(8)
3387(11)
1614 (7)
35(8)
92(15)
C(2A)
6642(9)
3760(13)
1251(7)
54(9)
lll(lG)
C(3A)
7077(8)
4683(12)
1485(7)
36(8)
97(15)
C(4A)
6831(9)
5248(13)
2052(8)
46(9)
108(15)
C(5A)
6157(9)
4377(12)
2413(7)
69(10)
93(15)
38
Table 8 - extended
B
33
'12
6
13
3
23
19(0)
40(1)
100(3)
21(3)
16(3)
20(3)
21(3)
34(4)
13(3)
26(4)
20(3)
16(3)
23(4)
18(4)
23(4)
28(5)
23(4)
15(4)
17(4)
28(5)
30(5)
36(6)
45(6)
46(6)
37(6)
33(5)
39(5)
29(5)
45(6)
43(6)
32(5)
-7(3)
8(5)
71(9)
12(11
-17(16
-35(13
-18(13
-9 (13
23(11
7 (15
■15(1^
-12(14
5(16
-5(18
20 (17
■11(17
4 (15
24 (15
■43(17
26(16
-5(18
■17 (19
45(18
58(19
19(23
■69(17
5(17
10(21
■12(19
■28(2?.
7(22
2(1)
11(3)
96(5)
6(6)
-8(6)
3(6)
-4(5)
7(8)
-6(6)
-1(8)
6(7)
13(6)
16(9)
7(9)
20(9)
-8(10)
12(9)
-4(8)
3(3)
-] (10)
•18(10)
-7(11)
4(12)
40(12)
44(12)
9(10)
31(10)
22(11)
9(11)
30(11)
11(11)
-4(2)
-13(4)
-15(7)
26(8)
7(13)
8(9)
12(10)
-15(12)
14(8)
7(12)
-21(11)
6(11)
20 (13)
0(13)
23(14)
5(13)
-2(12)
7(11)
-9(12)
30(12)
20(14)
15(15)
2(15)
20(15)
70(17)
•29(14)
4(15)
2(16)
46(16)
13 (19)
2(17)
39
Table 8 - continued
Atom X y z ^^^ ^22
C(1B) 6675(9) 2815(14) 3687(7) 61(9) 113(16)
C(2B) 7444(9) 2801(13) 4142(7) 59(9) 89(15)
C(3B) 7498(9) 3363(15) 4781(7) 56(10) 189(23)
C(4B) 6828(9) 4051(16) 4937(7) 59(10) 207(22)
C(5B) 6047(10) 4094(14) 4476(7) 73(11) 148(19)
C(1C) 664(9) 1226(12) 3750(7) 66(10) 73(14)
C(2C) 20(9) 872(12) 4199(7) 56(10) 96(16)
C(3C) -212(9) 1576(14) 4700(8) 32(8) 183(23)
C(4C) 184(9) 2563(12) 4813(7) 61(10) 112(17)
C(5C) 826(8) 2872(11) 4368(6) 60(8) 41(11)
C(1D) 593(9) 2121(12) 1437(6) 54(8) 83(14)
C(2D) -224(9) 1992(14) 1045(7) 56(9) 116(16)
C(3D) -951(9) 2410(12) 1345(7) 50(9) 105(17)
C(4D) -888(8) 2847(12) 2044(7) 42(8) 77(14)
C(5D) -69(8) 2975(12) 2447(6) 30(7) 63(12)
0(S1) 1418(9) 4904(10) 944(5) 190(13) 136(13)
C(S1) 1450(26) 4854(22) 182(12) 512(49) 196(30)
a 4 . .
All values are x 10 . The estimated standard deviations
are given in parentheses. The temperature factors are of
the form: exp[-(B^^h2 + 622^^^ "^ ^33^^ "^ ^12^^^ "^ ^13^^^ "^
3^ok-c) J .
40
Table 8 -
continued -
extended
^33
^12
^13
^23
39(6)
-11(22)
-24(11)
13(18)
39(5)
-24(21)
-4(11)
24(17)
32(5)
-59(24)
13(11)
-5(15)
18(5)
-47(26)
0(10)
-39(19)
28(5)
-90(25)
7(11)
0(18)
28(5)
-27 (19)
-3(11)
-20(15)
28(5)
-24(21)
7(11)
13(16)
44(6)
-21(21)
-26(11)
-5(19)
20(5)
16(19)
26(10)
-10(14)
28(4)
-31(19)
-7(9)
8(14)
28(5)
-4(20)
7(10)
-16(16)
34(5)
13(23)
-34(10)
-39(19)
42(6)
11(19)
-31(11)
50(16) '
51(6)
-13(20)
-8(11)
6(18)
40(5)
-30(18)
17(9)
7(10)
39(5)
67(23)
45(12)
-23(14)
59(11)
224(71)
194(38)
45(34)
41
Table 9
Final Parameters for Hydrogen Atoms for C£Co (Il^dpg„ ) (clan)
Atom
[Bonded to] Distance x y z B
H(B1)
303(9)
344 (12)
153
(8)
11
6(5
1)
H(B2)
352(7)
277(9)
43 9
(5)
4
3(2.
7)
H(2) [
C(2)]
0.84 (10)
514(7)
87(9)
325
(5)
4
3(2
8)
H(3) [
C(3)]
0.95(14)
627(9)
47(12)
260
(7)
9.
8(4
5)
H(5) [
C(5)]
0.80(10)
445(6)
54(8)
93
(5)
4
1(2
8)
H(6) [
C(6)]
1.00(10)
33G(7)
84(9)
152
(5)
4
7(3
0)
H(7) [
N(l)]
0.93 (11)
305(7)
107 (10)
264
(C)
5
9(3
3)
H(8) [
N(l)]
1.02(15)
382(9)
103(13)
332
(8)
11
7(4
6)
H(1A)
[C(1A)]
1.05(12)
558(7)
278 (10)
135
(6)
6
0(3
2)
H{2A)
[C(2A)]
0.94 (10)
680(6)
329(8)
89
(5)
4
0(2
.7)
H(3A)
[C(3A)]
1.18(15)
759(9)
514(13)
117
(7)
10
.5(4
8)
H(4A)
[C(4A)]
1.12(12)
711(7)
604 (10)
227
(6)
5
7(3
3)
H(5A)
[C(5A)]
0.86(9)
601(6)
525(8)
227
(5)
2
.4(2
4)
H(1B)
[C(1B)]
1.07(9)
654 (6)
236(8)
320
(5)
o
o
0(2
.6)
H{2B)
[C(2B)]
1.12(19)
796(11)
224(16)
398
(9)
14
.6(6
.6)
H(3B)
[C(3B)]
0.68(13)
792(9)
351(11)
487
(7)
9
1(4
.4)
H(4B)
[C(4B)]
0.74 (10)
690(7)
403 (9)
533
(6)
5
.3(3
.0)
H(5B)
[C(5B)1
0.55(14)
586(9)
406(12)
471
(7)
11
.2(4
.6)
H(1C)
[cdo:
0.81(13)
76(8)
69(10)
352
(7)
8
.3(4
.1)
H(2C)
[C(2C):
1.04(19)
3(12)
7(15)
403
(9)
15
.8(6
.3)
H(3C)
[coo:
1 0.96(12)
-63(8)
140(10)
504
(7)
8
.2(4
.0)
H{4C)
[C(4C)
1 0.92(12)
4(8)
305(10)
515
(6)
6
.0(3
.0)
H(5C)
[C(5C)
I 1.00(8)
106(5)
362(6)
447
(4)
0
.5(1
.9)
H(1D)
[C(1D)
1 1.05(9)
116(6)
175(7)
128
(5)
3
.0(2
.4)
H(2D)
[C{2D)
1 1.10(9)
-41(6)
160(8)
52
(5)
2
.8(2
.6)
H(3D)
[C(3D)
1 0.97(14)
-145(9)
219(12)
101
(7)
10
.1(4
.4)
H(4D)
[C(4D)
1 1.04(10)
-136(6)
343(8)
212
(5)
3
.8(2
.7)
H(5D)
[C(5D)
1 0.70(8)
25(5)
316(7)
224
(4)
1
.5(2
.0)
The hydrogen atom is given followed by the atom to which it
is bonded in brackets, the corresponding bond distance (A) ,
the positional parameters with estimated standard deviations
(x 10"*"-^) , and the isotropic thermal paiTmeters (A2) .
42
The scattering factors for cobalt, oxygon, nitrogen, and
29
carbon were from Hanson et al. , those for hydrogen wore
from Stewart et al . , and those for chlorine were from Doyle
and Turner. The observed and calculated structure factors
are given in Table B-2. Lists of final positional and thermal
parameters may be found in Tables 10 and 11.
Results and Discussion
The atomic numbering and thermal ellipsoids of C£Co-
{H2dmg) (dmg) (clan) , c£Co (H2dpg2) (clan) , and [Co (Hdmg) 2 (clan) 2]-
54
CI are shown in ORTEP drawings in Figures 1, 2, and 3, re-
spectively. The individual bond distances for these three
compounds together with those of tv;o related compounds, C€Co-
(Il2dmg) (dmg) (sulfa) and [Co (Hdmg) 2 (an) 2] C^, ^^ are tabulated
in Table 12. The corresponding bond angles are given in
Table 13.
In each case the tv;o dmg or dpg groups are approximate-
ly planar as demonstrated by the deviations from least-squares
planes in Tables 14-16. The dmg groups of each complex are
linked by two intramolecular hydrogen bonds (see Table 17) .
As in the case of C^Co (H2dmg) (dmg) (sulfa) ''^ the hydro-
gen bridges between the dmg groups in C^Co (H2dmg) (dmg) (clan)
were found to be asymmetrical with both hydrogen atoms bonded
to the same dmg ligand. The 0(21)-H(B2) and 0(22)-H(Bl) dis-
o
tances of 1.13(8) and 1.16(8) A, respectively, compared to
the 0(12) • • •H(B2) and 0 (11 ) • • -H (Bl) distances of 1.36(8) and
o
1.37(8) A indicate the formulation H2dmg and dmg for the two
43
Table 10 "
The Final Atomic Parameters for Nonhydrogen Atoms of [Co(Hdmg)2
(clan)2lC£.^
Atom
X
Y
z
^11
^22
Co
0(0)
0(0)
0(0)
817(11)
628(5)
C^(l)
0(0)
50000(0)
0(0)
2653(30)
664(12)
Cl{2)
32052(23)
26440(24)
55881(8)
5254 (48)
6743 (52)
0(11)
4450(2)
1508(2)
573(1)
97(4)
126(3)
0(12)
-3514(3)
531(2)
-1814(1)
125(5)
144(3)
N(l)
-846(3)
1678(2)
816(2)
116(5)
77(3)
N(ll)
2490(3)
1399 (2)
-160(2)
105(5)
83(3)
N(12)
-1339(3)
923(2)
-1288(1)
118(5)
91(3)
C(l)
97(4)
1928(3)
1978(2)
148(7)
90(3)
C(2)
2160(4)
2812(3)
2368(2)
195(8)
136(4)
C(3)
3103(5)
3034(4)
3474(3)
224(9)
231(6)
C(4)
1982(6)
2386(5)
4181(3)
317 (11)
311(8)
C(5)
-77(6)
1504(5)
3818(3)
320(11)
3 00(8)
C(6)
-1012(4)
1282(4)
2704 (2)
193(8)
185(5)
C(ll)
2176(4)
2274(3)
-990(2)
159(7)
76(3)
C(12)
-124(4)
1982(3)
-1665(2)
185(7)
87(3)
C(13)
3887(4)
3459(3)
-1239(2)
216(8)
116(4)
C(14)
-937 (5)
283C(4)
-2658(3)
289(10)
169(5)
^All values are x 10^ except thosu for Co, C£(l) and Cl{2)
which are x 10^. The estimated ^'^t^^'-^^^ ^^^^tTlrT oTlhe
qjven in parentheses. The temperature factors are of the
form: exp[-(BTL3_h + P22 33 12 13 2i
44
Table 10 - extended
^33 ^12 ^13 ^23
332(3) 226(12) 169(9) -43(6)
873(8) 451(29) 1194(26) 13] (15)
482(7) -1987(79) -431(28) -982(29)
57(1) 9(5) 11(4) -12(3)
57(1) 40(6) -20(4) 15(3)
45(1) 28(6) 30(4) -9(3)
47(1) 26(6) 30(4) -21(3)
41(1) 53(6) 7(4) -7(3)
47(2) 47(8) 27(5) -24(4)
63(2) -25(9) 59(6) -42(5)
72(2) -85(12) -3(8) -93(6)
49(2) 2(15) -11(3) -59(7)
51(2) -22(15) 64(8) ] (7)
52(2) -11(10) 36(6) -12(5)
52(2) 42(7) 73(6) -4(4)
46(2) 68(8) 5o(6) 6(4)
77(2) 12(9) 109(7) 16(5)
68(2) 68(11) 47(8) 75(6)
45
Table 1j .
Final Parameters for Hydrogen Atoms for [Co (Hdmg) 2 (clan)^^^'
Atom
[Bonded to] Distance x y z B
H(B1)[0(12)] 1.07(3) -408(8) -35(4) -133(3) 5.5(0.8)
H(2)[C(2)] 0.85(3) 280(4) 321(3) 190(2) 3.5(0.6)
H(3)[C(3)] 0.91(4) 447(6) 361(4) 3C6(3) 6.0(0.8)
H(5)[C(5)] 0.98(4) -92(6) 105(4) 431(3) 6.6(0.9)
H(6)[C(6)] 0.96(3) -248(5) 73(3) 244(.?) 3.9(0.6)
H(7)[N(1)] 0.88(2) -299(4) 146(3) 64(2) 2.1(0.5)
H(8)[N(1)] 0.94(2) -52(4) 262(3) 49(2) 2.7(0.5)
H(11)[C(13)] 0.90(4) 349(6) 440(4) -131(3) 5.7(0.8)
H(12)[C(13)] 0.89(4) 417(7) 315(5; -185(4) 9.0(1.2)
H(13)[C(13)] 0.91(4) 513(6) 353(5) -67(3) 7.3(1.0)
H(14)[C(14)] 0.86(4) -181(7) 217(5) -314(3) 9.0(1.2)
H(15)[C(14)] 0.80(5) -14(8) 300(6) -274(4) 10.0(1.3)
H(16)[C(14)] 1.01(5) -213(8) 337(6) -252(4) 11.0(1.4)
•
^The hydrogen atom is given follov7ed by the atom to which it
is bonded in brackets, the corresponding bond distance (A) ,
the positional parameters with estimated standard deviations
(x lO"*"-^) , and the isotropic thermal parameters (a2) .
u
n o
•H -P
0)
o
c
Q)
Q)
U XI
•H
E 0)
O >
n3 .c;
CU Ifi
£ <u
tri U
C 0)
•H .H
o
e
o
x:
Cn
Q)
O 4->
(N (tj
K S
H CN
• 'C
Q) ^ C
M C nJ
^ nj
Cn>H W
H o e
-^ o
^ -p
— <D
^ 0^
ty> O
f: U
TJ Ti
<N>i
O <U
O XI
=v> Eh
U
H-4 •
o w
c o
•H W
(0 --H
U <-i
E-«
>i
■P
i5 p o
47
(0 0)
-P
b- -P
C -I
o
c
0
•H
V^
Ct
u o
•H >
E ««
o x:
+j
(d Q)
O 0
x: o
-p o
tP o
•H
o o
Xi in
tn W
\xi U
CM O
lO'd
0) w d
3 o
Cri • CO
P4 r-' O
rH m
V
— Ci
^ 0)
tT" O
D. W
fa ^o
CM >i
O Ci
u .a
u
O CO
Tl
tn-iH
f-; o
? fi.
CU
P5 H
E-i (fl
f^ E
O V^
O
< -P
49
g
0)
Xi
+»
•o
c
Id
c
■H
d)
u
-H
E
0
4J
fO
Q)
x;
+j
•
Xi
CP o
c
-p
•H
-p
?
•H
fO
0
G
^
0
<D
w
U
C,
:3
o?
<u
tnU
0)
■H
r— »
.Q
t,
CM
„,-^
a)
c
>
(0
ra
-H Xi
o
* — •
w
CN
e
, — .
0
D^-P
a
(0
xi
a
c
—
0)
o
u>
u
0
^ ''
M-t
>i
o ^
cy<
Q)
c
.d
•H
H
^
nJ
v^
•
nci
Cu
•H
W
o
Eh
CO
Q^.
D4
O
C
rH
<
OJ
51
52
Tabic 12
Selected Interatomic Distances (X) in Some Cobaloxime
Complexes with Their Estimated Standard Deviations.^
C£Co(H2dmcj) (clan) C-CCo (Il2dpg) 2 (clan)
Co-N{l)
1.999(6)
1.946(11)
Co-N(ll)
1.872(5)
1.908(9)
Co-N(12)
1.884 (5)
1.935(11)
N(]l)-0(11)
1.3 37 (6)
1.356(11)
N(12)-0(12)
1.329(6)
1.316(12)
N(ll)-C(ll)
1.311(8)
1.258(15)
N(12)-C(12)
1.308(8)
1.292(16)
C(ll)-C(12)
1.457 (9)
1.455(16)
C(ll)-C(13)
1.488(10)
1.487(17)
C{12)-C(14)
1.487(10)
1.536(18)
0(11) ...0(22)
2.497 (7)
2.540(11)
0(11)-H(B)
1.37 (8)
1.41(]4)
0(12)-II(B)
1.36(8)
1.30(10)
Co~CZ(l)
2.257 (2)
2.244(4)
Co-N(21)
1.908 (5)
1.887(10)
Co-N(22)
1.906(5)
1.897 (9)
lsj(21)-0(21)
1.348 (6)
1.321(12)
N(22)-0(22)
1.359(6)
1.337(11)
N(21)-C(21)
1.280(8)
1.331(16)
N(22)-C(22)
1.288(8)
1.313(14)
C(21)-C(22)
1.468(9)
1.483(15)
C(21)-C(23)
1.486(11)
1.4 57 (17)
C(22)-C(24)
1.498(11)
1.464 (17)
0(12) -..0(21)
2.479(7)
2.460(12)
0(21)-H(8)
1.13(8)
1.16(10)
0(22)-H(B)
1.16(8)
1.17(15)
♦Distance given is for O (11) —O (1 2 ' ) ^0 (12) •••0 (11 ' )
^Values for (^©(H^dmg ) (an)^]C£. are listed with atomic number
ing corresponding to the compounds of this work.
53
Table 12 - extended
C£Co(H2dmg2)(sulfa) '^ [Co (n2ding2)(clan) 2] C£ [Co (H2dmg2)(an) 2] C£
2.023(8) 2.003(2) 2.001(5)
1.870(8) 1.906(2) 1.885(6)
1.884(8) 1.889(2) 1.889(5)
1.323(11) 1.340(3) 1.353(6)
1.344(11) 1.362(3) 1.333(6)
1.289(14) 1.299(3) 1.286(10)
1.293(13) 1.290(3) 1.303(10)
1.494(16) 1.477(4) 1.463(7)
1.532(17) 1.483(4) 1.482(12)
1.488(16) 1.485(4) 1.476(11)
2.507(11) 2.495(3)* . 2.491(8)*
1.50 1.44(3) 1.29
1.60 1.07(3) 1.21
2.235(3)
1.905(8)
1.896(8)
1.326(10)
1.338(11)
1.292(12)
1.290(14)
1.447(17)
1.494(17)
1.488(16)
2.479(11)
0.90
1.04
54
Table 13
SG^o.oted Intramolecular Angles (°) in Some Cobaloximo Complexes
with Their Estimated Standard Deviations.^
C^Co(H dmg2) (clan) C£Co(h2dpg2) (clan)
N(l)--Co-N(ll) 90.5(2) 94.8(4)
N(l)-Co-N(12) 91.5(2) 92.1(4)
N(l)-Co-N(21) 88.4(2) 87.1(4)
N(l)-Co--N(22) 88.6(2) 88.6(4)
N(ll)-Co N(12) 82.6(2) 81.3(4)
N(ll)--Co-N(22) . 98.8(2) 100.0(4)
N(ll)-Co-N(21) 178.8(2) 177.5(4)
N(12)-Co-N(21) 98.1(2) 97.0(4)
N(12)-Co-N(22) 178.6(2) 178.5(4)
N(21)-Co-N(22) 80.6(2) 81.7(4)
C£(l)-Co-N(ll) 90.6(2) 87.7(3)
C^(l)-Co-N(12) 90.6(2) 89.1(3)
C£(l)-Co-N(21) 90.5(2) 90.4(3)
C£(l)-Co-N(22) 89.4(2) 90.2(3)
cr.(l)~Co-N(l) 177.8(2) 177.4(3)
Co-N(l)-C(l) 119.7(4) 118.6(8)
Co-N(ll)-O(ll) 121.9(4) 123.3(7)
Co-N(12)-O(12) 122.2(4) 121.2(8)
Co-N(21)-O(21) 123.2(4) 123.5(8)
C;o-N(22)"0(22) 123.3(4) 120.7(7)
Co-N(ll)-C(ll) 116.0(4) 116.7(8)
Co-N(12)-C(12) 115.6(4) 114.1(9)
Co-N(21)-C(21) 116.6(4) 116.8(8)
Co-N(22)-C(22) 117.0(4) 117.4(8)
0(11)-:](11)-C(11) 122.1(5) 119.7(9)
0(12)-N(12)-C(12) 122.3(5) 123.8(11)
0(21)-N(21)-C(21) 120.3(5) 119.4(10)
0(22)-N(22)-C(22) 119.8(5) 121.7(10)
N(ll)-0(11) -0(22) 99.7(3) 95.9(6)
N(12)-0(12)-0(21) 99.7(3) 99.2(7)
N(21)-0(21) -0(12) 96.9(3) 98.2(7)
N(22)-G(22) -0(11) 96.0(3) 100.1(6)
55
Table 13 - extended
46 52
C£Co(H dmg2)(sulfa) [Co (H2dmg2)(clan) 2] C^ [Co (H2dmg2)(an) 2] C£
90.5(3) 89.8(1) 91.5(4)
91.7(3) 93.2(1) 93.0(5)
89.3(3)
87.8 (3)
82.0(4) 80.8(1) 80.8(3)
98.7(4)
179.3(4)
98.7(3)
179.2(4)
80.6 (3)
89.6(3)
88.5(3)
90.5(3)
91.9(3)
179.7(2)
119.1(6) 119.7(1) 119.5(7)
123.0(6) 121.3(1) 121.4(6)
122.6(6) 122.7(1) 122.9(7)
121.6(6)
123.6(6)
116.4(7) 116.9(2) 116.0(9)
117.4(7) 117.7(2) 117.8(9)
116.3(7)
116.8(7)
120.5(9) 121.8(2) 121.8(12)
120.0(8) 119.6(2) 119.2(10)
122.2(8)
120.1(9)
98.3(6)
97.8(6)
99.2(5)
96.8(6)
56
Table 13 - continued
C£Co(H dmg ) (clan)
C£Co(H2clpg2) (clan)
N(ll)
N(ll)
N(12)
N(12)
N(21)
N(21)
N(22)
N(22)
C(13)
C(14)
C(23)
C{24)
-C ( 1 1
-C(ll
-C(12
-C(12
-C(21
-C(21
-C(22
-C(22
-C(ll
-C(12
-C(21
-C(22
-C(12)
-C(13)
-C(ll)
-C(14)
-C(22)
-C(23)
-C(21)
-C(24)
-C(12)
-C(ll)
-C(22)
-C(21)
112.8 (6)
122.9(6)
113.1 (6)
122.5(6)
113.5(6)
112.4 (7)
112.3 (6)
123.2(6)
124.2(6)
124.4 (6)
124.1(6)
124.4 (6)
112.1(10)
125.6(11)
115.5(11)
119.5(11)
112.2(10)
120.9(11)
111.9(10)
126.0(11)
122.3 (11)
125.0(11)
126.8(11)
122.2 (10)
The atomic numbering of Co (H2dmg2) (an) 2c/* has been
changed to correspoiid to that of compounds of this work.
57
Table 13 - continued - extended
C£Co(H2dmg2)(sulfa)'^^ [Co (H2dmg2)(clan) ^]Cl [Co (H2ding2)(an) ^]C.^^
113.3(9) 112.2(2) 112.4(10)
125.0(10) 125.0(2) 124.6(16)
110.7(9) 112.5(2) 112.2(9)
124.0(10) 124.1(2) 125.0(16)
113.1(9)
120.7 (10)
113.1(9)
122.9(10)
121.7(10) 122.9(2) 123.0(12)
125.3(10) 123.4(2) 122.9(13)
12 6.1(10)
123.6(10)
58
ligands. This is in contrast to results reported for various
Co(H2dmg2) complexes^^ ''*''' ''^' ^° ' '^^ as well as for Fo(H2dmg2)--
(imidazole) 2/^^ Ni (H2dm92) , '"'^ and Cu(H2dmg2), where either
the hydrogen bridges were assumed to be equidistant from the
tv70 oxygen atoms or the ligands were monoprotonated. The
assumption of a symmetrical bridge may have in part been based
on the earlier TR spectroscopic work on M(H2dmg2) complexes
where the v^eak band due to nn O-II vibration near 1725 cm
was assumed to indicate a very sl)ort aiid symmetrical O-H-O
bridge. "^^'^^ McFadden and McPhail"'"'' reported the structure
of Co(H2dmg2) (CH3) (H2O) ii' which both bridging hydrogen atoms
if ordered are required crystallographi cally to be on one dmg
ligand. No comment" was made concerning the bridging hydro-
gen atoms.
Although both hydrogen bridges in C^Co {H2dpg2) (clan)
appear to be shifted toward one dmg v.'here the 0(21)-H(B2) and
o
0(22)-H(Bl) distances are 1.16(10) and 1.17(15) Awhile the
0(12)--H(B2) and 0(11)-H(l!l) distances are 1.30(10) and 1.41
o
(14) A, the experimental uncertainty is too large to show
that result to be significant.
The hydrogen bridges in [Co (Hdmg) 2 (clan) 2] c£ are not
symmetrical and each dmg is singly protonated. The 0(12)-H(B1)
distance is 1.07(3) A and the 0 (11) • • -H (bl) distance is 1.44
o
(3) A. The gross structure is very similar to that of
tCo(Hdmg)2(an) 2lC-^-
Bowman et al. suggested the N-0 distance to be a sen-
sitive indicator of the position of the bridging hydrogen.
59
Table 14
Deviations and Equations of Selected Least-Squares Planes
in C£Co(H2dmg) (dmg) (clan)^
° +3
(a) Deviations (A x 10 )
Plane 1
Plane 2
Plane 3
Plane 4
Co
5
-1796
0*
72
0(11)
25
-2574
209
0(12)
-23
2533
80
N(ll)
_2*
-1260
175
N(12)
2'-'
1218
140
C(ll)
4*
-775
251
C{12)
-4*
682
220
C{13)
73
-1633
413
C(14)
41
14 98
330
0(21)
34
2602
-22
0(22)
-79
-2548
-55
N(21)
48
1269
1*
N(22)
7
-1197
_1*
C(21)
113
795
-2*
C(22)
94
-673
2*
C(23)
230
1664
24
C(24)
143
-1482
-17
N(l)
2004
-41
0*
C(l)
2752
-12*
0*
C(2)
3092
5*
1197
C(3)
3767
5*
1204
C(4)
4105
-9*
18
C(5)
3790
3*
-1193
C(6)
3112
8*
-1204
Cl{2)
4946
-28
5
ClU)
-2252
-29
(b) Coefficients of the Plane Equation ^8
Ax + By + Cz = D
Plane A B C D
1 0.8529 0.4975 0.1583 1.6954
Table 14 - continued
^The deviations of atoms used to define the plane are
marked with an asterisk.
GO
Plane
A
B
C
D
2
0.9995
0.0282
0.0142
1.6347
3
0.0208
-0.3098
0.9506
1.7440
4
0.8174
0.5536
0.1594
1.8108
61
Table. 15
Deviations and Equations of Selected Least-Squares Planes
a
in C^.Co(H2dpg ) (clan)
° +3
(a) Deviations (A x 10 )
Plane 1
Plane 2
Plane 3
Plane 4
Co
19
-1932
0*
29
0(11)
-56
1350
-101
0(12)
122
-2807
192
N(ll)
17*
160
2
N(12)
-18-*
-1881
24
C(ll)
-30*
-945
-30
C(12)
30*
"2118
62
C(13)
-179
-1048
-195
C(14)
94
-3571
149
0(21)
-5
60
0(22)
-37
-87
N(21)
-43
-8*
N(22)
28
8*
C(21)
-9
13*
C(22)
-1
-13*
C(23)
93
133
C(24)
-58
-89
N(l)
1958
-148
0*
C(l)
2755
-13*
0*
C(2)
3166
4*
-1171
C(3)
3843
16*
-1184
C(4)
4069
-20*
10
C(5)
3720
5*
1166
C(6)
3076
14*
1205
Cl{2)
4901
-1
-10
c^(l)
-2223
24
C(1A)
676
C(2A)
510
C(3A)
-529
C(4A)
-1417
C(5A)
-1255
62
Table 15 - continued
Plane 1 Plane 2 Plane 3 Plane 4
C(1B) 1094
C(2B) 1237
C(3B) 427
C(4B) -641
C(5B) -821
C{1C) 1232
C(2C) 1380
C(3C) 3C1
C(4C) -734
C(5C) -827
C(1D) 571
C(2D) 554
C(3D) -230
C(4D) -874
C(5D) -8^38
r p
(b) Coefficients of the Plane Equation"^"
A>: + BY I- Cz " D
Plane
A
B
C
D
1
0.1954
-0.9752
-0.1036
3.3476
2
-0.2301
-0.9634
0.1374
] .9549
3
0.5744
0.0297
0.8181
-7.1571
4
0.1976
-0.9769
-0.0813
3.2302
^The deviations of atoms used to define the plane are
marked with an asterisk.
63
Table 16
Deviations and Equations of Solected Least Squares Planes
in po ( Hdmg ) ( c 1 an )2 ]Cl^
(a) Deviations (A x lO'*'"^ )
Co
0(11)
0(12)
N(ll)
N(12)
C(ll)
C(12)
C(13)
C(14)
N(l)
C(l)
C(2)
C(3)
C(4)
C(5)
C(6)
Cl{2)
Plane 1
Plane 2
Plane 3
10
-1772
0*
36
2519
14
-5 2?
0*
1902
0*
428
1*
2567
-1*
1677
26
4046
11
217 3
-
2009
-28
0*
2799
-2*
0*
3030
2*
1194
3758
-1*-
1208
4257
0*
37
4048
0*
-1168
3312
1*
--1174
5159
-33
53
59
(b) Coefficients of the Plane Equation
Ax + By + Cz ^- D
Plane
A
B
C
D
1
-0.4938
0.67 23
0.5515
-0.0101
2
-0.5672
0.8236
0.0096
1.7716
3
0.7336
0.6506
-0.1594
0.0000
The deviations of atoms used to define the plane are
marked with an asterisk.
64
X
I
Q
VO VO >X> 00
CO
ro CM (N
o n
VD
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r-
^
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o
'S*
r-
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fO
00
fVJ
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VO
VO
in
VD
r^i
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in
r^
VO
VD
r-
ut
iH
iH
rH
rH
iH
rH
iH
rH
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r-l
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vor~<Ntj*vD"^invo ^r~-r^ OrH
f^f^cTvor^rooin rj-OrH ro'^i'
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CQ O
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r-( rH
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CJ CN
CN
CN
rH
o o o
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0)
u
o
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0)
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o
c
r
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(0
65
Dissimilar N-0 bond lengths should indicate the hydrogen is
not symmetrically located and is closer to the dmg with the
longer bond. This holds true in C£Co(H2drag) (dmg) (clan) where
the N-0 distances appear to be different. The N (21) -0(21)
o
and N(22)-0(22) distances of 1.348(6) and 1.359(6) A in the
diprotonated dmg are longer than the N (12) -0(12) and N(ll)-
o
0(11) distances of 1.329(6) and 1.337(6) A in the dianionic
dmg. Using the significance test described by Cruickshank
and Robertson the N (21) -0(21) distance is possibly longer
than the N (12) -0(12) with a t^ value of 2.2 4 and the N(22)-
0(22) bond is significantly longer than the N (11) -0(11) bond
with a t value of 2.59. Also, in [Co (Hdmg) 2 (clan) 2] C£ the
o
N(12)-0(12) bond of 1.362(3) A is significantly longer than
o
the N (11) -0(11) bond of 1.340(3) A, v/here the bridging hydro-
gen atom is bonded to 0(12). Neither the N-0 distances nor
the bridging O-H distances in c£Co (H2dpg2) (clan) are signi-
ficantly different. In [Co (Hdmg) 2 (an) 2] CZ where the hydrogen
atoms are not significantly removed from a symmetrical posi-
tion, the N (12) -0(12) distance is shorter than that of N(ll)-
0(11). The difference in these two bond lengths of 1.333(6)
and 1.353(6) A is of possible significance (t^ = 2.36). The
sensitivity of the N-0 bond as an indicator of the bridge
position is questionable. The N-0 bonds are not significant-
ly different in C'CCo(H2dmg) (dmg) (sulfa) when both bridging
hydrogen atoms are shifted to one dmg. In the closely rela-
ted dimethyl ( 3, 3 '-trimethylenedinitrilo) bis- (butan-2--one-
oximato) cobalt (III) complex the two N-0 distances are e::ual
6C
even though an asyinmetric hydrogen bridge is clearly indi-
cated by the difference Fourier syntheses. Although a
difference in the N-0 bond lengths as a function of protona-
tion is reasonable, there are very few structures so precise-
ly determined that this comparison can be made. Hence, no
general conclusion may be made. Hov;evcr, when a significant
difference in the N-0 distances has been found and the bridg-
ing hydrogen atom has been precisely located, the hydrogen
atom is associated with the longer N-0 bond.
Another point in support of the formulation C£Co(H2dmg)-
(dmg) (clan) is the difference in the Co-N bond lengths. The
o
Co-N distances on the ll2dmg side are 1.908(5) and 1.906(5) A
o
compared to distances of 1.872(5) and 1.884(5) A on the dmg
side. The differences in the Co-N bond lengths are signifi-
cant and the shorter distances involve the dianionic group.
This holds true in the other cases where the presence of both
H2dmg and dmg ligands has been indicated. In CcCo (H2diTig) (dmg) -
(sulfa) ' and in Co (H2dmg2) (CII^) (H2O) ^■'" the distance.s from
the cobalt atom to the dianionic ligand are shorter than the
distances to the neutral H2dmg ligand. This is not the case
in C£Co (ri2dpg2) (clan) where the distances from the cobalt atom
to what would be the dpg didnionic ligand, 1.9 35(11) and 1.908
o
(9) A, appear to be longer than the corresponding distances
to the n2dpg ligand, 1.887(10) and 1.897(9) A. These differen-
ces together with the apparent positions of the bridging hydro-
gen atoms (vide supra) in C£Co(H2dpg2) (clan) are of question-
able significance.
67
For the mononegative ligands in [Co (Hdmg) „ (clan) 2] C^
the Co-N distances are significantly different. However, N(12)
which is l:ionded to the protonated oxygen atom is closer to the
cobalt atom than is K(ll) with distances of 1.889(2) and 1.906
o
(2) A, respectively. The same relationship holds in Fe(?Idmg)2-
55
(imidazole) 2 r the only other M(Hdmg)2 complex whose X-ray
structure precisely places one bridging hydrogen on each dmg
and shov/s a significant difference in the metal to nitrogen
distance.
/in unsyixmietrical hydrogen-bonding system involving two
similar atoms may be fluxional. In such a system two equili-
brium positions, i.e. potential v/ells, exist for the hydrogen
atom. Each of these positions may be considered as having tiie
hydrogen atom covalently bonded to one atom and hydrogen bon-
ded to the other. For the system to be truly fluxional the
energy barrier betv/een the tv/o positions must be thei:aally
accessible. Depending on the relative depths of the potential
wellr. , tlie energy barrier betv^een them, and the thermal ener-
gy of the system the position of the hydrogen atom as indi-
cated by X-ray diffraction experiments would vary. Because of
the diffuse appearance of the bridging hydrogen atoms of the
M(n2dmg2) complexes in difference Fourier syntheses, a fluxio-
nal system with two potential wells of unequal depth seems
reasonable. The relative populations of the two positions will
depend soniev7hat on the depths of the potential wells. The ex-
perimentally determined position (or positions) of the hydro-
gen atom v/ill reflect these populations. As the depths of the
68
potential wells approach equivalence and as the energy barrier
between them becomes smaller the position of the hydrogen atom
will become experimentally more uncertain. A fluxional sys-
tem could, in part, account for tlie difficulty iii precisely
locating the bridging hydrogen atoms in M(H2dmg2) complexes.
The orientation of the 4-chloroaniline ligand in the
complexes of this study is quite intriguing. A projected view
down the Co-N(l) bond for C£Co{H2dmg) (dmg) (clan) is shovm in
Figure 4. A similar view for [Co (Hdmg ) 2 (clan) 2] C£ is given in
Figure 5(a) and one for C^Co(H2dpg2) (clan) is given in Figure
5(b) . In CeCo(H2dmg) (dmg) (clan) , as in C£Co(H2dnig) (dmg) (5:.ulfa)^^
the aromatic ring of the aniline is oriented over the dianio-
nic dmg ligand. The orientation angle, i.e. the dihedral
angle between the planes having Co-N(l) in common with one
containing C(l) and the other containing the bisector of the
angle N (11) -Co-N (12) , for C£Co (K2dmg) (dmg) (clan) is 0.9° and
for C£Co(n2dmg) (dmg) (sulfa) is 1.8° us given in Table 18. In
[Co(Hdmg) 2(clan) 2]C£ and in [Co (Hdmg) 2 (an) 2]C£ the ben7ene
rings are skewed relative to the equatorial ligands with ori-
entation angles of 53.9° and 58.3°, respectively. It seems
significant that in the former pair of Co (H^dmg) (dmg) type
complexes the rings align while in the latter pair of Co (H-
dmg) 2 type complexes the rings are skewed. Although tho ben-
zene ring of the aniline is tipped from being parallel to the
dmg plane by ca. 30° as in other similar complexes (see Table
18) the alignment and the distances between the two planes in
C£Co(H2dmg) (dmg) (clan) suggest a ir-type interaction. The
o
-I
C) CN
u Ui
CP o
-H u
CJ
M
O
I
o
o
o
l-l
n)
0)
•H
>
(U
+)
o
0)
•n
O
M
&.
70
O
o-
CQ
.X
O
o
CM
o
o
o
XI
c
nJ
=^
CJ
o
(M
6
in w
QJ O
O
:3
I
o
o
O
H
I
>
♦d
(U
-p
o
0)
-n
O
U
72
73
en
o
fH
c
E
o
u
o
CM
a,
K
O
O
u
rH
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CM
o
10
0)
tT>
en
C
c
<
■H
+>
r-]
o
fO
0)
V4
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tJ
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0)
<u c
X
4J (tj
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c ^
o
H PM
CN
in
oi
CO
CO
in
in
CO
CO
00
o
m
CM
00
ro
00
CM
CT\
CO
00
rsi
CO
CO
en
CO
CM
00
in
■^
00
en
00
n
CO
00
CJl
CO
CN
ro
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PI
■^
•^
L.O
1
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rH
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rt
r'
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X! Q)
G
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0) <D M-l a)
c c 0) x:
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in N
(U C W MH
T! « -H 0
X!
W '* M
•HO) O
X (U -M
r-l ^J C U
fd OJ
0) G r-l U5
C -H p^ -H
(0 X5
rH W
fij e • (u
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1 o T) fd
^ JQ C
■-' Sh Id -
(0 ^
en o '•'H
0) ^^
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X) x: —
ns -P S ^
H 0
>, -u
C X! 0
•H u en
T! C
^3 (1) >i-H
0) r; X! fc
C -H +J
■H MH tJ Ci
M-' GJ (D 0
Q) ^ii C o
li -H
tn iH m
tn -H 0)
nj tJ OJ
CN c
CO en (ti
G) <D •^^ rH
c; c Pj
(C3 feJ fo
r-l rH
a,(u Q) •
c —
en nj cn
0.) • rH CN
5-1 — P^ ^
(d f>J CJ
0 rH
^v_- . r(3
en u TJ C
1 C rd
+J t3 (d
en c tT> -
(d fd -H —
dJ rH iH
•
rH V <N
^~,
^ 0 —
CM
(U rH C U
rH
M rH -H
— '
(d "-'rH -
s
O -H -^
1
'3' C <N
0
- fd CN
u
0 ^ ^
1
+J CM Q) 2
,-,
rH x;
r-i
r-1 — • 4-1 ^
.-1
S —
■ —
Cn 4H rH
z
eu * 0 CN
c -- --
0)
(0 rH D-> 22
r-(
r-i ,-^ C
tr^
C^ — -H >i
C
(d s?; >H X!
(d
74
0)
c
o
y,
I
00
I-l
Q)
iH
a
EH
<N
'd
O
u
CM
rH
o
■•d
(N
O
U
o> o-i ^-^ Cf^
• • o •
(N 1X> CO >X)
rO OO rH CO
n
00
in
o r>- — , r-
• • o •
CO CTi CO <N
n CO M 00
00
m
in
b->
c
•-H
4-i
O
QJ
W
CO
>H
O)
O
c;
4J
(C
CS'
n
•^'
r->
"*
vf
Ln
n
cH
1
1
1
1
1
1
1
M
04
r-i
^_l
rH
rg
cs
en
n
75
distances from the dmg plane to C(l), C(2), and C{6) given
o
in Table 14 are substantially less then the 3.40 A interpla-
nar distance in graphite. A proton transfer occurring from
one Hdmg ligand to the other would increase the electron den-
sity within the ir-system of the formed dianion. An interac-
tion by v/hich the filled it orbitals of the dmg overlap v;ith
the empty ii* orbitals of the aniline v;ould enhance the basi-
city of the aniline ligand. The complex formed v;ould be stron-
ger than might be expected based on the K, value alone. This
same argument applies to C-£Co(H-dmg) (dmg) (sulfa) which was
the first example of ligand-induced proton shift in a mole-
cular complex. While the positions of the bridging protons
in C-^Co (H^dmg) (dmg) (clan) and [Co (Hdmg) 2 (clan) 2] C^ are well
defined, the bridge in C.£,Co (Hpdpg-^) (clan) is ill defined and
the orientation angle of 36.7° is an intermediate value (see
Table 18). The 0---0 distances in this complex shov; more
variation than those in other related complexes as sho\;n in
o
Table 12. The 0.08 A difference in the 0...0 distances is the
same as for the corresponding N-'-N distances. The N(12)'''
N(21) separation is 2.836(15) A and the N (11) • • 'N (22) dis-
o
tance is 2.914(13) A. Concurring with these observed distan-
ces, the N(12)-Co-N(21) angle of 9 7.0(4)° is more acute than
the N(ll)-Co-N(22) angle of 100.0(4)°. None of tlie other com-
pounds examined shows any significant differences in the cor-
responding distances and angles between the diglyoxime li-
gands .
76
A comparison of mean bondiny distances for each of the
reported Co(H2dmg2) complexes may be made from Table 19. There
appears to be little variation in the average Co-N distances
or in the average dimensions within the equatorial dimethyl-
glyoximc ligands as a function of the axial ligand.^
Those complexes having chloride as an axial ligand show
a definite variation with the nature of the trans ligand. The
longest Co-Ct distance is found where tpp is the trans li-
gand. This is not surprising since phosphines are knovm to
have a very large trans- influence but the small influence
the tpp ] igand exerts on the trans -chlorine atom compared to
40
that of an ammonia ligand is unexpected. There is no sig-
nificant difference in the Co-N(l) distance involving a clan
ligand v;hether it is trans to a chlorine atom or trans to
another clan ligand. The trans -influence appears to occur in
Co (K2dii-ig2) complexes but not to a large extent.
The Co-Y distances in the XCo(H2dmg2)Y complexes where
Y is a ligand with an sp nitrogen, increase in the following
order of Y: NH^ < an '>- clan < sulfa (see Table 19). This
series can be rationalized in terms of the relative K, 's for
sulfa (2.3 X lO"-*-^),^^ clan (9.6 x lO""'--'-),^^ aniline (4.0 x
10~ ),^^ and ammonia (1.3 x 10~ ) . Bruckner and Randaccio
did not consider the J'j-'s of the different nitrogen donors
in their argument of the trend in trans- influencing ligands,
X, upon the Co-N bond. The same Co-N distances were used for
NH^ and aniline complexes in their argument for basing the
extent of trans - in fluerrce on the a-donor power of the trains
77
U) i-H
u
C^
o n
O
I
CO
<U
o
r-!
o
u
I
K
O
I
o
u
c
i~l
,Q —
(0
Q)
O
G
tH
4J
CO
■H
Q
•O
c;
o
pq
o
H
o
-IJ
U-l
o
>.
u
i
CO
I
o
u
I
o
u
IT)
CN
n
o ^--
vo u~>
(N
CO
0-)
en
tN
cr.
^
LD
ro
r-
Lfl
ro
oi
oo
fO
01
in oj
K) Lfl
CNi v-o ro ro
ro
00
CO
CO
o
9
r-l
00
CO
O
CO
CJ>
CO
LTl
cy.
co
CO
o
CT\
CO
05
CO
CO
CO
CO
rs
in
^3- o") rH •=3* r^
^s" LO "-H r~-
^ ro m r- LO
CM CN OJ c^J r^
rvj CN C^J CN c^
rr>
a\
uo
ro
"^
■=;r
o
ro
o
o
CN CN Cvl 04
<^ CM
00 -^
C-) i-f) Ln
a^ CO >xi 01 tn
cri
C?i
o
o
ca
CT>
(N
o
og
V.O CM
c?i ro
L'1
O
o
o
crv
cr>
cr»
CM CN v'N
O
CM
U
O
CJ
cv^ e^) cJ
u u 0
(3
ro
O Ci
CN "-^
C
U
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79
ligand as are presented here.
In comparing C-^Co (H2dpg2) (clan) with C-CCo (H2dmg) (dmg)
(clan) the distances from the cobalt atom to the equatorial
nitrogens in the H2dpg complex are longer and the distances
to the axial ligands are shorter in the same complex. Because
the phenyl substituents are inductively more electron with-
drawing than methyl groups , Hdpg should be a v/eaker Lev;is
base than iJdmg. The equatorial distances to the Hdpg should,
therefore, bo longer. From an electronic standpoint the co-
balt ion in the Hdpg complex would be more positively charged
and a better Lev;is acid toward the axial ligands than in the
Hdn^g complex. From a steric point of view the axial ligands
are afforded a wider path of approach and v/ill, therefore, be
closer to the central cobalt ion. v/hen the equatorial ligands
are farther away .
The benzene rings in the clan ligands of Ci^.Co (IlTdmg^J "
(clan), C£Co (H2dpg2) (clan) , and [Co (Hdmg) 2 (clan) 2]CC are pla-
nar (see Tables 14-16) having average C-C values of 1.376(3),
o
1.380(10), and 1.378(3) A, respectively, with individual
values reported in Table 20. The phenyl rings of the Hdpg li-
gands of C^Co (H2dpg2) (clan) are also planar with pertinent
values and equations of least-squares planes given in Table 21
The crystals of C-£Co (H2dmg) (dmg) (clan) are held together
by six hydrogen bonds where there are eight hydrogen atom.s
capable of hydrogen bonding. Relevant hydrogen-bonding data
are presented in Table 17. Although the 0-H---0 bridges be-
tween the H2d;ag and dmg groups are not synv.aetrical, th.-; O-II
80
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E
■H
4J
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V(
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0)
x:
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(1)
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UUUUUUUUI I
^ I I I I 1 I I 1 — —
o ^^^^^^-^-— M-^
^^r-Hr-ICNCO'^Lnv^rH^^^^
tnuuuucjuuui I
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CT^ r^ iH iH CNJ 00 T in vo •^- '—
J- ^ ^ ^ ^- >- ^ -- — =V •^^
81
Table 21
Bond Distances, Bond Angles, and Least-Squares Planes of
the Phenyl Rings in C£Co (H2dpg2) (clan) with The.ir Estimated
Standard Deviations.
23 24
(a) Distances
C{n)-C{lt)
C(n)-C{5.e)
C{ll)-C{2l)
C{2l)-C{3l)
C(3£)-C(4.£)
C(4^)-C(5^) .
(b) Angles (")
C(n-2)-C(n)-C(U)
C(n-2)-C(n)-C(5£)
C(n)-C(U)-C(2£)
C{ll)~C{2l)-C{3l)
C{2Z)-C{3l)-C(Al)
C(3£)-C(4l)-C(5£)
C(4£)-C(5£)-C(n)
C(5£)-C(n)-C(U)
o
(c) Deviations (A
Rings
C(n)
C(U)
C{2l)
C(3l)
C{4l)
C(5^)
C(n-2)
n = 13
£ = A
14
B
D
1.3G3(18) 1.411(20
1.421(20) 1.396(20
1.368(19) 1.371(20
1.370(21) 1.367(20
1.352(20) 1.391(23
1.37.1(20) 1.390(20
123.9(11) 119.3(12
119.9(11) 120.9(12
122.8(13) 120.6(13
119.5(13) 119.3(14
120.5(13) 121.0(14
120.0(14) 120.4(14
121.0(13) 118.4(14
116.2(12) 119.8(13
X
1.370(19) 1.426(17)
1.356(17) 1.458(18)
1.432(19) 1.385(19)
1.351(21) 1.401(20)
1.371(23) 1.397(20)
1.409(18) 1.397(18)
120.9(11) 121.7(11)
121.2(11) 120.6(11)
122.3(12) 122.6(12)
117.0(13) 117.7(13)
122.2(14) 122.5(13)
118.7(13) 120.2(13)
121.7(12) 119.0(12)
117.9(12) 117.7(11)
+ 3
10 ) from Least-Squares Planes of Phenyl
2
-7
10
-10
5
-2
-3
41
-14
-31
48
-20
-24
172
-3
8
15
-29
3
19
-16
3
-12
24
-28
20
-7
20
(d) Coefficients of the Plane Equation PX + QY + RZ = S
P Q R S
Phenyl A
Phenyl B
Phenyl C
Phenyl D
-0.5815
-0.4144
-0.6482
-0.1592
0.5296
-0.7511
0.3950
-0.8986
-0.6176
0.4990
-0.6509
0.4088
4.7459
3.1793
4.0341
1 . 3 6 ^: 2
82
distances arc longer than might be expected. The tv;o hydrogen
atoms on N(l) of the clan ligand both hydrogen bond to differ-
ent water molecules. The hydrogen atoms of one water mole-
cule, 0(w2), form reasonably strong hydrogen bonds to 0(12)
and C£(l) . The hydrogen atoms on 0(wl), however, have only
short contacts with angles indicating only v;eak hydrogen bonds.
V^hile [Codldmg) 2(clan) 2]C£ and C£Co (H2c3pg2) (clan) both
exhibit the hydrogen bonding botv.'een the equatorial ligands,
Ci^Co(n2dpg2) (clan) has no interraolecular hydrogen bonds. While
the hydrogen atom on the solvent molecule was not located, a
hydrogen bond may exist between 0(S1) and 0(22). Each mole-
cule of [Co(ndmg) 2 (clan) 2]C^ possesses two intermo] ocular hy-
drogen bonds. Each clan molecule shows a hydrogen bond from
N(l) to the 0(11) of another molecule. The other hydrogen on
each N(l) is hydrogen bonded to the ionic chloride. Relevant
hydrogen-bonding data for these two compounds are also presen-
ted in Table 17.
o
All intermolecular distances less then 3.6 A were cal-
culated and carefully examined. No unusually short intermole-
cular distances were found.
Ligand-induced proton shifts may be of biological sig-
nificance. Since proton transfers in living systems are rela-
tively comnon, the study presented here provides an impor-
tant examination of orientation effects and enhanced stabili-
ties which may be achieved by a small shift of one proton.
CHAPTER 5
A NOVEL BINUCLEATING LIGAND: THE CRYSTT^ AND MOLECULAR STRUC-
TURES OF 1 , 4-DIHYDRAZINOPHTHALAZINEBIS (2-PYRIDINIUMCARBOXAL-
DIMINE) NITRATE DIHYDllATE AND iJ-CHLGROTETRi^J'i.QUA [1 , 4-DIHYDRA-
ZINOPHTHALAZINEBIS (2-PYRIDINECARBOXALDIMINE) ] DINICKEL(II)
CHLORIDE DIHYDRATE
Binuclear complexes of chelating ligands have been of
interest recently for their potential activation of other
6 8~ 7 3
ligands at an accessible bridging site and for their mag-
netic properties. ^'*''^^~^° The structure of [Ni2C£{H20) ^. (dhph-
py)]Cl^ shows the planar chelating ligand, dhphpy, to be ca-
pable of binding two metal atoms simultaneously. In that com-
plex, a bridging site betv/een the nickel ions is occupied by a
chloride ion. Therefore, at lea-st one bridging ligand in addi-
tion to dhphpy may be accommodated by M2dhphpy complexes.
V7hile the study of magnetic interactions betv/een metal
ions through bridging atoms in svxch systems is convenient and
theoretically significant, the catalytic possibilities of this
type system are exceptional. The nitrogen- fixing enzyme nitro-
genase has been considered to contain a polynuclear active
•4. 6,7
site. '
Although the mechanism of the reduction of N2 to KH^ by
nitrogenase is not understood N2 is believed to be coordina-
ted to the metal ions of the enzyme. ' ' Nitrogenase
has been shown to reduce a wide variety of small molecules
7
which contain a triple bon i , The distance betv/een the rt'etal
83
84
ions should be of importance in the activation of tliose mole-
cules. In the complexes of Robson and coworkers and of
8 3
Okawa et al. the metal-metal distance is essentially con-
trolled by a single bridging phenoxide ion. However, in dhphpy
complexes the metal ion separation is fixed at tx greater dis-
tance by the geometry of the chelating ligand. Therefore/ lar-
ger molecules which are reduced in the presence of nitro-
genase, e.g. N^, N^; ^2^* ^2'^2' ^"^ HCN, should bo suitable
for incorporation as bridging molecules opposite the N-IJ
bridge of dhphpy. The syntheses and X-ray structures of
H2dhphpy (NO^) 2-H20 and [Ni2C£ (H2O) ^ (dhphpy) ] Ci^, • 2H2O were
undertaken to examine the nature of the accessible bridging
site in coniplexes of this type ligand.
So3.ution and Refinement of the Structure
of H2dhphpy (N03)'2 • ^^2^
The direct method of syn^olic addition was ust-d in v;hich
the signs of tv/o hundred large E's v.'ere assigned. All four-
teen nonhydrogen atoms of the ligand within tlie asymmetric
unit were located in an E-map computed from the signed K
values. Two Fourier syntheses v.-ere used to validate the selec-
ted model, locate the remaining nonhydrogen atoms, and re-
fine the atomic parameters. The refinement is outlined in
Table 5. The observed and calculated structure factors are
given in Table B-3. The final positional and thermal parame-
ters are presented in Tables 22 and 23.
85
CO
CN
o
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<c
v£)o^'5ro^r^o^-J>Xl^ooc-^<^r^r-a^oa^y:)c^
III I I I -H
i^inoror--<T'UororHmLni.oinrocofMLOix>*J3
fo i;!' CN r>T <' m CN CN m CM CM ^ VD m r~- m
fo ro ro 'y oT ro ■=? -^ "^^ ^ ro CO CO n ■^^ c^i LD fo <^
Q^f.-)(NiiHr^cx)roincyi':j'cy>^ir)n'^Ln'3'r-^
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c ^ ^1 fr, (^ VD oT CM "Nf cq r~ r~- OT <H ro n o^ ro "C
cor^r-r~-CT>c»iH'3<r-(aNr-r-r-cDcri.Hw5CNco
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CN
CN
CN
lHrHroc^'*or-oO(Xl^ooLDr-coo^vrcoc7^
CNCNfOCnC-JCNCNfOrOCNCNOTCNCN^JDtnrHinCO
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r-roLnr^cor->-DiHcorMooor-vi)cN<sD'i'COuD
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86
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87
Solution and Refinement of the Structure
of [Ni2Ct:(H20) 4 (dhphpy) ]C£-:;-2H20
The position of Ni(l) was determined from a sharpened
three-dimensional Patterson function. The positions of the
remaining atoms were determined in a manner analogous to that
used v;ith C^CoCH-dmg) (dmg) (clan) . After the hydrogen atoms
were located they were included in further refinement with
each having an isotropic thermal parameter one unit higher
than the refined isotropic value for the atom to which the
hydrogen atom v/as bonded. A sutrmary of the refinement is gi-
ven in Table 5. The scattering factors for the nonhydrogen
29
atoms were from Hanson et al . and the hydrogen scattering
30
factors from Stewart et al. Lists of observed arid calcu-
lated structure factors are given in Table B-4. The final
positional and thermal param.sters are listed in Tables 24
and 25.
Results and Discussion
The atomic numbering and thermal ellipsoids of K2dhphpy"
(N02)2*2H20 are shown in Figure 6 and those of [Ni2Cc(H20)^
(dhphpy) ]C£2*2H20 are shown in Figure 7. Selected interato-
mic distances of both compounds are listed in Table 26 and
corresponding angles Z'-re given in Tables 27 and 28. Both com-
pounds crystallize v;ith the cationic complexes, their anions,
and water molecules linked in a three-dimensional hydrogen-
bonded network. The postulated hydrogen bonds in the struc-
tures are listed in Table 29. Diagrams illustrating the pack-
88
Tabic 24
The Final Atomic Parameters^ of the Nonhydrogen Atoms for
[Ui^Cl iU^O) 4 (dhphpy ) ] 0^3 . 2H2O
Atom
e
11
Ni(l)
11817(7)
17289(5)
9891(3)
4 4 2(5)
Ni(2)
11346(6)
-4660(5)
13854 (3)
407(5)
C^{l)
1046(1)
315(1)
650(])
63(1)
C£{2)
1196(2)
4767 (1)
2115(1)
86(2)
C£{3)
1297(2)
-1548(1)
3350(1)
69(1)
C£(4)
1288(2)
3725(2)
4540(1)
90(2)
0(1)
-362(4)
1864(3)
639(2)
55(3)
0(2)
2743(4)
1634(3)
1329(2)
55(3)
0(3)
-423(3)
-532(3)
1026(2)
48(3)
0(4)
2664(3)
-435(4)
170,8(2)
48(3)
0(5)
1626(4)
-520(4)
-194(2)
54(3)
0(6)
1072(4)
5047 (5)
3678(2)
74(4)
N(l)
1178(4)
140C(3)
1690(2)
50(4)
N(2)
1153(4)
576(3)
1834(2)
48(4)
N(3)
1265(4)
2854(3)
1801(2)
74(5)
N(4)
1258(4)
2873(3)
1324(2)
53(4)
N(5)
1143(4)
-469(3)
2395(2)
55(4)
N(6)
1165(4)
-1007(3)
2025(2)
45(4)
N(10)
1234(4)
2554 (4)
433(2)
54(4)
N(20)
1163(4)
-3776(4)
1227(2)
55(4)
C(I)
1233(5)
2052(4)
1992(3)
42(4)
C(2)
1251(5)
1919(4)
2495(3)
36(4)
C(3)
1280(5)
2594(5)
2826(3)
50(5)
C(4)
1300(5)
2410(5)
3302(3)
56(5)
C(5)
1288(5)
1559(5)
3450(3)
51(5)
C(6)
1260(5)
2?7(4)
3136(2)
47(5)
C(7)
1236(4)
1057(4)
2649(2)
29(4)
C(8)
1182(4)
394(4)
2288(2)
29(4)
C(10)
1281(6)
3550(4)
1076(3)
71(6)
C(ll)
1291(5)
3337(5)
578(3)
52(5)
Table 24- extended
89
22
33
'12
'13
23
273(4)
106 (1)
-66(8)
224(5)
14(4)
244(3)
92(1)
2(B)
184(4)
13(4)
31(1)
10(0)
-10(2)
26(1)
-2(3)
35(1)
14(0)
8(2)
18(1)
0(1)
50(1)
17(0)
46(2)
39(1)
3 7(1)
72(1)
25(1)
-58(3)
26(2)
-1(1)
42(3)
21(1)
3(5)
26(3)
6(3)
40(2)
21(1)
-6(5)
29(3)
2(3)
58(3)
18(1)
-5(5)
23(3)
22(3)
C9(3)
12(1)
17(5)
14(3)
-2(3)
62(3)
17(1)
1(5)
26(3)
-3(3)
111(5)
18(1)
1(7)
35(4)
-6(4)
23(2)
11(1)
-2(5)
25(3)
-1(2)
24(2)
11(1)
-1(5)
25(3)
1(2)
26(2)
15(1)
-14(6)
38(4)
-3(3)
31(3)
14(1)
-12(5)
29(3)
3(3)
25(2)
9(1)
1(5)
19(3)
1(2)
26(?)
11(1)
-1(5)
21(3)
3(2)
41(3)
14(1)
5(5)
33(3)
10(3)
32(3)
13(1)
13(5)
26(3)
0(3)
24(3)
14(1)
-9(6)
26(4)
0(3)
30(3)
13(1)
-11(6)
14(4)
-6(3)
37(4)
14(1)
-12(7)
27(4)
-10(3)
44(4)
14(1)
-8(7)
26(4)
-17 (^i)
55(4)
12(1)
-17(7)
23(4)
-11(4)
40(4)
9(1)
-2(6)
18(4)
1(3)
32(3)
10(1)
• -8(6)
15(4)
-3(3)
28(3)
12(1)
-5(6)
20(3)
-2(3)
30(3)
20(2)
-7(7)
41(5)
7(4)
36(3)
17(1)
-3(7)
29(4)
7('l)
90
Atom
Table 24 - continued
y 2
'11
C(12)
1343(6)
4055(5)
270(3)
83(7)
C(13)
1353(7)
3839(6)
-202(3)
86(7)
C(14)
1308(6)
2992(6)
-348(3)
73(6)
C(15)
1251(6)
2361(5)
-17(3)
59(6)
C(20)
1143(5)
-1829(4)
2053 (3)
54(5)
C(21)
1147(5)
-2273 (4)
1604(3)
48(5)
C(22)
1149(6)
-3175(5)
1577(3)
64(6)
C(23)
1165(6)
-3554(5)
1149(3)
77(6)
C(24)
1204(6)
-3048(5)
758(3)
76(6)
C(25)
1195(5)
-2157 (5)
812(3)
55(5)
^All values are x 10 except for those of Ni(l) and IU(2)
V7]i.i.ch are x 10^, The estimated standard deviations are
given in parentheses. The temperature factors are of the
form: exp[-(B^^h2 + 332^^ + ^33^^
12 13 2o
91
Table 24 - extended - continued
^22
^33
^12
^13
^23
49(4)
20(2)
-19(9)
36(6)
19(4)
68(5)
17(2)
-27(10)
34(G)
21(5).
68(5)
20(2)
7(9)
47(6).
15(5)
60(5)
14(1)
-6(8)
27(5)
5(4)
-»
29(3)
14(1)
0(6)
29(4)
6(3)
31(3)
14(1)
10(6)
25(4)
5(3)
32(3)
. 21(2)
6(7)
31(5)
3(4)
39(4)
21(2)
15(8)
33(5)
-6(4)
43(4)
19(2)
8(8)
24(5)
-13(4)
39(4)
16(1)
2(7)
24(5)
-6(4)
92
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Table 28
Selected Angles in [Ni2C£ (H^O) ^ (dhphpy) ] C^^ • 2il 0
Atom Angle Atom Angle
N(l)-Ni(l)-C£(l) 98.0(2) N
N(l)-Ni(l)-N(4) 76.8(2) N
N(l)-Ni(l)-2vI(10) 155.7(2) N
N(l)-Ni(l)-0(1) 91.1(2) K
N(l)-Ni(l)~0(2) 90.3(2) N
N(4)-Ni(l)-C^(l) 174. G(2) N
N(4)-Ni(l)-N(10) 78.9(2) N
N(4)-Ki(l)-0(1) 87.8(2) N
M(4)-Ni(l)-0(2) 91.1(2) N
N(10)-Ni(l)-C^(l) 106.3(2) N
N(10)-Ni(l)-O(l) 88.5(2) N
KM10)-Ni(l)-O(2) 89.6(2) N
0(1)-Ni(l)-Ci:(l) 90.9(2) 0
0(i)-Ni(l)-0(2) 178.0(2) 0
0(2)-Ni(l)-C£(l) 90.3(2) 0
N(10)"C(11)"C(12) 122.2(7) N
C(ll)-C(12)-C(13) 117.8(8) C
C(12)-C(13)-C(14) 120.3(9) C
C(13)-C(14)-C(15) 118.4(8) C
C(14)-C(15)~N(10) 122.3(8) C
C(15)-N(10)-C(ll) 119.1(7) C
N(10)-C(ll)-C(10) 116.2(7) N
C(12)-C(ll)-C(10) 121.6(7) C
C(ll)-C(10)-N(4) 114.7(7) C
C(10)-N(4)-N(3) 125.9(6) C
N(4)-N(3)-C(l) 115.3(6) N
N(l)-C(l)-N(3) 115.7(6) N
C(2)-C(l)-N(3) 122.7(6) C
N(l)-C(l)-C(2) 121.6(6) N
C(l)-N(l)-N(2) 121.8(6) C
C(l)-C(2)-C(7) 116.8(6) C
2)-Ni(2)-Ci(l) 97.8(2;
2)-Ni(2)-N(6) 76.5(2
2)~Ni(2)-N(20) 154.8(2:
2)-Ni(2)-0(3) 93.1(2:
2)--Ni (2)-0(4) 89.5(2:
C)~Ui{2)~Cl{l) 174.1(2:
6)-Ni(2)-N(20) 78.2(2:
6)-Ni(2)-0(3) 90.4(2:
6)-Ni(2)-0(4) 91.2(2:
20)-lii{2]--Cl{l) 107.5(2;
20) --Ni (2) -0(3) 88.3(2;
20)-Ni(2)-O(C) 89.8(2;
3)-Mi(2)"Cf-(l) 88.2(2;
3)-Ni(2)-0('0 177.2(2;
4)-Ni(?)-C,C(3) 90.5(2;
20)-C(21)-C(22) 121.9(7
21)-C(22)-C(23) 118.7(7;
22)-C(23)-C(24) 120. 2(P'
23)-C(24)--C(r:5) 117.7(8;
24)-C(25)-K(20) 122.6(7
25)-N(20)-C(21) 118.8(6;
20) -C (21) -C (20) 116.7(6;
22)-C(21)-C(20) 121.4(7;
21)-C(20)-N(6) 113.8(6;
20)-N(6)-M(5) 123.4(6;
6)--N(5)-C(£) 113.8(51
2)-C(8)-N(5) 116.3(6;
7)--C(8)-M(5) 121.8(6;
2)-C(8)-C(7) 121.0(6;
8)~N(2)-N(1) 120.8(51
2)-C(7)-C(a) 117.0(6;
102
Table 28 - continued
Atom Angle Atom Angle
C(l)-C(2)-C(3) 123.5(6) C (6) -C (7 ) -C (8 ) 123.5(6)
C(2)-C(3)-C(4) 119.7(7) C (5 ) -C ( G) -C (7 ) 119.4(G)
C(3)-C(4)-C(5) 120.1(7) C (4 ) -C (5) -C (6 ) 121.6(7)
Ni(l)-N(l)-N(2) 122.4(4) N.i (2 ) -N (2 ) -N (1) 123.3(4)
Ni(l)-N(l)-C(l) 115.8(5) NJ.;2)-N(2)-C(8) 115.9(4)
Ni(l)-N(4)~N(3) 115.9(4) Ni (2 ) -N (6) -N ( 5) 117.3(4)
Ni(l)-N('l)-C(]0) 118.2(5) Ni(2)-N(6)-C(20) 119.1(5)
Ni(l)-N(10)-C(ll) 111.9(1.) Ni(2)-H(20)-C(21) 112.1(5)
Ni(l)-N(10)-C(15) 128.9(5) Ni (2) -N (20) -C (25) 129.1(5)
Ni(l)-C£(l)-Ni(2) 98.4(1)
The estimated standard devjations are given in parentheses,
103
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104
ing and hydrogen bonding in Il2dhphpy (NO-^) 2* 2H2O and in
[Ni2C£{Il20) 4 (dhphpy) )C£3-2H20 are presented in Figures 8
and 9.
The most noticeable difference in the structures of the
two dhphpy ligands is that H2dhphpy (NO-^) 2 * 2il20 contains a
tv/ofold rotation axis while the nickel complex docs not. In
both cases the ligand is approximately planar (see Table 30) .
The nickel atoms and the bridging chloride of [hi.2Cl (II2O) ^-
(dhphpy) ]Cf o • 2H2O lie slightly "below" the least-squares
plane of the ligand (Plane 3) and both hydrazone portions are
pivoted generally about an N(3)---N(5) axis witli both C(14)
and C(24) "above" the plane. However, in the protonated li-
gand one hydrazone is pivoted "upv,ard" and the other "down-
v/ard" as required by the twofold axis. Also, the hydrazone
"arm5'. " in the nickel complex are drawn tov^ard each other com-
pared to the pro tone'! ted form as indicated by the bond angles
within the "arms." All of tl.e pyridine ringn are rotated
about tlje C(nO)-C(nl) bond relative to the phthala^ine plane
with the pyridine nitrogen atoms tipped toward the coordina-
ted species. In [Ni2C£ (lUO) . (dhphpy) JCZ^- 21I2O the pyridine
containing N(10) is rotated to a much greater extent than
that containing N(20). This is shov/n by tho deviations from
plane 4 (Table 30) of N(10) and C(12), 0.121 and 0.222 A,
compared to the deviations of N(20) and C(22), 0.148 and
o
0.161 A. The rings of the phthalazine fragment in each com-
pound appear twisted relative to each other but by less
than 2".
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1.11
All bonding distances involving nonhydrogen atoi/.s are
normal. The N-N distances in both compounds range from
o
1,363(7) to 1.374(4) A and are comparable to the N-N dis-
° 84
tance in 4-FPYTSC of 1.36b (3) A, Since, this distance in
both the phthalazine and hydrazone groups is significantly
shorter than the accepted N-N single bond distance, 1.44±4
° 85
A, and since the ligand is planar, a delocal3.zed system
is presumed to exist. In agreement with this assumption the
C(nO)--N distances are longer than the pure C--N double bond
distance and are all equivalent to the related C-N distance
O O A
in 4-FPYTSC, 1.275(3) A."" All other distances within the
ligand are not significantly different from those in [Ni(dh-
ph) (H^0)2C^^ -21120.^^
All Ni-N distances in [Ni^C-f. (H^O) ^ (dhphpy) ] Cf.3- 2H2O are
within the range of reported bonding distances of nickel (II)
with aromatic nitrogen atoms (2.00 to 2,112 A).
The bridging chloride is not symmetrically located be-
tween the two nickel atoms with Ni-'C-£ di.:;t3nces of 2.374(2)
o
and 2.387(2) A. The appearance of this bridge is remarkably
similar to that in di-y-chloro-sym-trans-dichlorobis- (2,9-
p o
dimethyl-l,10-phenanthroline) dinickel (II) • 2 chloroform
where the Ni-C distances are 2.378(3) and 2.394(3) A. Also,
the Ni---Ni distance, 3.602(2) A, and Ni-cC-Ni angle, 98.0(1)°,
o
in that compound are equivalent to the 3.603(1) A separation
and 98.36(7)° angle in [Ni2C£ (H2O) g (dhphpy) ] 0^3 • 2H2O. This
distcince betv/een the nic}:el citoms is somewhat shorter than
112
the 3.791(4) 7v distance found in the [Ni (dhph) (H2O2] 2C^4 *
2H,.0 complex reported by Andrew and Blake where both
bridges are phthalazinc nitrogen atoms. The separation be-
tween the nickel atoms in the dhphpy complex, however, is
o
substantially longer then the Ni''-Ni distance of 2.879 A
in the doubly oxo-bridged complex of Hoskins, Robson, and
7n
Schaap. All these inter-nickel distances are much greater
than tv;ice the covalei;t radius of nickel and must be a func-
tion of the bridging atomj.
The distorted octahedral coordination geometry about
each nickel atom in [Ni^Ci^ (1120) ^ (dhphpy) ] C>e3- 2H2O is comple-
ted by two v:ater molecules which lie on a line almost perpen-
dicular to the llgand plane. The Ni-0 bond distances are
87
typical for water coordinated to nickel (11) ranging from
2.070(G) to 2.117(G) A.
A degree of uncertainty exists concerning the poiitJ.ons
of hydrogen atoms abouL 0(1) in Il2dl]phpy (NO^) 2 * 2H2O. The
o
0(1) -n(l) distance appears to be very short, 0.78 A, while
o
the N(10)-H(py) distance appears to be very long, 1.21 A.
Although the locations presented for the hydrogen atoms are
the most reasonable interpretation of the difference map in
terms of rcrk heights, distances, and M-O-H angles, other
areas of positive density exist about the N(l), 0(1) , and
N(10) positions. Disorder may exist with alternate forms ha-
ving N(l) protonated or having a "coordinated hydronium ion."
Complexes of dhph:y structurally provide a promising
113
uni-iuolecular system for the incorporation of a small mole-
cule at a bridging position. Dinitrogen has been reported as
a bridging ligand connecting two metal complexes in the
y-dinitrogen-bis{ [1, 2-bis (dimethylphosphino) ethane] hydr ido-
[q- (1/ 3, S-trimethylbenzene) jmolybdenum} cation ard similar
89
compounds. No complex has been reported which could retain
its structural integrity after the removal of a bridging di-
nitrogen. The structures presented here suggest complexes of
ligands similar to dhphpy may have such a capacity.
CHAPTPjR 6
MODELS OF PROPOSED INTERMEDIATES FOR THE CATALYZED CYPT T-
ZATION OF ACETYLENES: THE CKYST/iL AND MOLECULAP STRUCTUPFq
OF l-(Tr-CYCL0PENTADIENYL)-l-TRIPHi^NYLPII0SPIiINE-2 3 ^ ^^"-'^^^^
TETRAKIS{PENTAFLU0R0PHENYL)C0RALT0LE AND 1- (tt -CYCLOPFNTA
DIENYL) -l-TRIPHENYLPIIOSPIJINE-2 ,3 , 4 , S-TETFJ^KIS (PENTAFLuiRO-
PHENYL) RHODOLE
The catalysis of tho oligornorization of acetylenes by
tran.sition metal complexes has been extensively studied. ^^
A reaction mechanism involving a metallo-cyclopentadiene
intermediate has been suggested^"^^ for the trimerization of
two molecules of acetylene v^ith one of olefin in the pre-
scencc of NiBr^Ctpp)^, Ni (CO) ^ (tpp) 3, and ether nicJ.el cat-
alystF:. Metal-containing hererocycles, metallocycles, have
been implicated^^" ^^"^^ as intermediates in the react: onr. of
acetylenes v/ith Tr-cycIopentadienyJdicarbonyl-metal complexes
in which the metal was cobalt, rhodium, or iridium. Yamazaki
et_ea. on the bar.is of chemical reactions assigned a
metallocyclic structure to a phosphine-containing cobalt
complex isolated from the reaction of diphenylacetylene with
Co(cp) (tpp)!^ and isopropylmagnesium bromide. They also
isolated the same product from the reaction of excess
diphenylacetylene with Co(cp) (tpp)^. A preliminary report
of the structure of a cobaltacycle formed by the reaction of
Co(cp) (tpp) (PhCiCCO^Me) with dimethyl maleate has been
reported.
114
115
15
Rausch and Gastmger prepared C. (f ph) .Co (cp) (tpp) by
the reaction of bis (pentafluorophenyl) acetylene with r-cyclo-
pentadienylcarbonyltriphenylphosphinecobalt. The analogous
rhodium compound was prepared by the reaction of the corre-
15
spending rhodium compound.
9 7
Except for one preliminary report no structural data
have been available for cobaltacyclopentadiene metallocycles.
Therefore, the X-ray diffraction stjrucLural analysis of
C. (fpii) 4C0 (cp) (tpp) v/as undertaken. The corresponding rhoda-
cycle was studied for comparison with this cobaltacycle and
related compounds.
Structure Solution emd Refinevaent
for C4 (fph) 4Co"(cp) (tpp) ~
The heavy atom method was used in vjhich the positions
of the cobalt and phosphorus atoip.s were estimated from a
sharpened Patterson function. A Fourier synthesj.s based on
these atoms v/as used to estimate the positions of eighteen
additional atoms. Successive Fourier syntheses revealed the
locations of all nonhydrogen atons in the c;ompound. A differ-
(Bnce Fourier synthesis at that point revealed a region be-
tween the cobaltacycles which v;as of relatively high electron
density. Because this density v/as diffuse no additional ato-
mic positions were estimated before starting refinement, R =
0.27. Three cycles of least-squares refinement with indivi-
dual isotropic theriual parameters reduced R to O.l'l. A differ-
ence Fourier synthesis again revealed relatively high eloc-
116
tron density in the same location as Lefore.
Because of the discrepancy of the calculated density
3 3
(1.423 g/cm ) from the measured density (1.59 g/cm ), solvent
molecules were presumed to be in the crystal. The deep red
14
crystals of the compound were grown from Skelly C which is
a saturated hydrocarbon fraction boiling betv.'een 88 aiid 9 8°C
and consisting mainly of n-heptane, ^-j^^i^' ^^ two solvent
molecules were in the unit cell the calculated densiity would
3
be much nearer the measured value at 1.55 g/cm . Several
maxima were observed in the difference Fourier synthesis v/ith-
in the region of high electron density. The distances between
these points and the angles made by lines connecting them did
not reasonably approximate a hydrocrirbon chain.
The thermal parameters were converted to their aniso-
tropic equivalent and nine least-squares cycles using a block
approximation to the matrix reduced R to 0.077. The sliifts
of all parameters during the fineil cycle were less than one-
tenth of their resi^cctivc estimated standard deviations. A
difference Fourier synthesis calculated at this stage again
suggested the presence of an ill-defined solvent molecule.
Although the distribution of the peaks, which were not v;ell
resolved, suggested a C-, oi' Cg chain, a closer examination of
the distances and angles within the group shov.'cd them not to
reasonably approximate a hydrocarbon chain.
Six peaks were selected which closely retained their
positions in the final ?'ourier summation before refinement
and in the difference Fourier syntheses just discussed and
117
which seemed the most reasonable in approximately a hydrocar-
bon chain. These locations were used isotropically as carbon
atoms together with the seventy-three refined positions from
the third full-matrix least-squares cycle used anisotropical-
ly in a structure factor calculation and in three cycles of
block approximation least-squares refinement. Although almost
all the poorly matched reflections (|FqV)^ - ^Valc^'*^^^ ^^~
proved, a Fouiier synthesis revealed peaks at positions shif-
ted to a less reasonable distribution from the linear hydro-
carbon approximation used. The refinement was terminated at
this point. An outline of the refinement is presented in
TaDle 5.
Scattering factors for cobalt, phosphorus, fluorine,
29
oxygon, and carbon v;cre taken from Hanson c t a ]. . A list of
14
observed and calculated structure factors is available.
Structure Solution and Refi.neiuent
for C4 { fph) 4lZh (cp) (tpp)
The method of isomorphous replacement was used for the
solution of the structure of C. (fph) ,Rh(cp) (tpp) . The cell
constants of C^ (fph) .Co (cp) ( tpp) and C^ (fph) 4Rh(cp) (tpp) as
reported in Table 4 are very similar with differences of less
than one percent. The positional parameters from the third
cycle of full-matrix least-squares refinement for trie non-
hydrogen atoms in the isomorphous compound C. (fph) 4Co(cp) (tpp)
were used in a structure factor calculation and a difference
Fourier synthesis with the C^ (fph) ^P.h (cp) ( tpp) data. The
structure factor calculation res\iltod in an R of 0.17 and the
118
difference Fourier synthesis revealed no major structural
differences in the tv;o compounds. The same positional para-
meters were used in an isotropic least-squares refinement of
the C, (fph) ,Ill-i(cp) (tpp) data. A summary of further refinement
is given in Table 5.
A difference Fourier synthesis after refinement suggest-
ed the presence of an ill-defined solvent molecule. As in the
3
case of the" cobaltacycle the calculated density, 1.47S g/cm ,
3
is significantly less than the density of 1.60 g/cm obtained
from flotation measurements of the yellow crystals. If two
molecules of n-heptane are assumed within the unit cell the
3
calculated density v;ould be 1.60 g/cm .
An attempt to fit a linear molecule to peaks in the
difference Fourier synthesis was also unsuccessful and was
not pursued.
The scattering factors used v.-ero taken from Hanrion
29
et al. Tlic observed and calculated structures are listed m
Table B-5.
Results and Discussion for
C4{fph) ^Co(cp) (tpp) and C4 (f ph) 4Rh (cp) (tpp)
The. final positional and thermal parameters for the.
nonhydrogen atoms of both C. (f ph) .Co{cp) (tpp) and C^(fph)^-
Rl-i(cp) (tpp) are listed in Table 31. The atonic numbering and
thermal ellipsoids of the cobaltacycle are shown in Figure 10.
The atomic numbering of the rhodacycle is analogous. Selected
bond distances and angles for the two compounds are listed
119
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127
in Tables 32 and 33. Least-squares planes and deviations are
given in Table 34.
The molecules are metallocycles with the metal atom also
bonded to the cyc]opentadienyl ring and to the triphenylphos-
phine ligand. The C(l) to C{4) fragment in both compounds is
planar with the largest deviation from the best plane being
0.015 A in the cobalt compound and 0.017 A m the rhodium
compound. The metal atoms, however, are significantly dis-
placed from the plane in the direction of the cp ring by
-0.203 and -0.239 A. This perpendicular displacement is simi-
9 8
lar to that found in other similar metallocycles.
The metallocycles may be considered as a dolocalized
diena with the metal atom a-bonded to the two carbon atoms
of the ring, C(l) and C(4). The Co-C bond distances, 1.995
(11) and 1.993(11) A, and the Rh-C bond distances, 2.060(12)
and 2.067(11) A, are similar to various values given by
Churchill. ^^ Values of 1.979(1) A"''^ and 1.990(5) A^ have
more recently been reported for Co~C bonds in ccbaloxime
complexes. Mague '■^"'^'^ has reported structures of similar
rhodacyles in which the Rh-C distances are 2.000(11), 1.964
(11), 2.047(16), and 1.998(16) A. Also, Cotton and Norman
o
report a singi.e-bcnd covalent radius of 1.39 A for Rh(ITI).
When this value is added to half the 1.485 A suggested length
for a single-bond between sp carbon atoms the Rh-C dis-
o
tance is predicted to be 2.13 A. The observed Rh-C distances
where rhodiuj.i has a formal oxidation number of ^•l are shorter
than r.he abc/e prodicted single-bond distance. T'ais iliffer-
128
Talkie 32
Selected Bond Distances (A) of C^ (f ph)^M(cp)(tpp) (M=Co,Rh)
with Their Estimated Standard Deviations in Parentheses.
M = Co Rh
M-C(l) 1.995(11) 2.060(12)
M-C(4) 1.993(11) 2.067(11)
H-P 2.234(3) 2.293(2)
M-C(51) 2.157(12) 2.286(13)
M-C(52) 2.121(13) 2.261(14)
M-C(53) 2.119(11) 2.250(13)
M-C(54) 2.104(9) 2.238(10)
M-C(55) 2.133(12) 2.268(12)
C(l)-C(2) 1.326(15) 1.343(16)
C(2)-C(3) 1.467(16) 1.457(16)
C(3)-C(4) 1.335(15) • 1.354(15)
C(l)-C(ll) 1.487(16) 1.498(17)
C(2)-C(21) 1.523(16) 1.497(16)
C(3)-C(31) 1.481(15) 1.478(16)
C(4)-C(41) 1.493(16) 1.492(17)
P-C(60) 1.848(11) 1.858(12)
P-C(70) 1.843(11) 1.821(10)
P-C(80) 1.834(12) 1.820(13)
C(51)-C(52) 1.463(20) 1.429(22)
C(52)-C(53) 1.400(15) 1.420(17)
C(53)-C(54) 1.426(18) 1.424(20)
C(54)-C(55) 1.433(16) 1.422(17)
C(55)-C(51) 1.457(17) 1.431(18)
129
Table 33
Selected Bond Angles (°) of C4 (fph) 4M (cp) (tpp) with Their
Estimated Standard Deviations Given in Parentheses. (M=Co,Rh)
M = Co Rh
M-C(l)-C(2) 112.1(8) 115.5(8)
C(l)-C(2)-C(3) 116.8(9) 114.9(9)
C(2)-C(3)-C(4) 114.8(9) 115.5(9)
M-C(4)-C(3) 113.1(7) 114,8(8)
C(l)-M-C(4) 82.4(4) 78.3(4)
P-M-C(l) 103.0(3) 101.6(3)
P-M-C(4) 95.2(3) 93.3(3)
C(ll)-C(l)-M 127.0(7) 123.3(8)
C(ll)-C(l)-C(2) 119.6(9) 119.4(10)
C(21)-C(2)-C(l) 123.9(9) 124.1(10)
C(21)-C(2)-C(3) 119.2(9) 120.9(9)
C(31)-C(3)-C(2) 119.7(9) 119.7(9)
C(31)-C(3)-C(4) 125.5(5) 124.9(10)
C(41)-C(4)-C(3) 119.8(9) 120.3(9)
C(41)-C(4)-M 127.0(7) 124.9(7)
C(51)-C(52)-C(53) 108.1(11) 108.3(12)
C(52)-C(53)-C(54) 109.6(10) 108.8(11)
C(53)-C(54)-C(55) 107.7(10) 106.9(11)
C(54)-C(55)-C(51) 108.0(10) 109.3(11)
C(55)-C(51)-C(52) 106.3(10) 106.8(11)
130
Table 34
Deviations from and Equations of Some Lease-Squares Planes of
C4(fph)^Co{cp) (tpp) and C^ (fph) ^Rh (cp) (tpp) .^
° +3
(a) Deviations {h x 10 )
Atom
Plane 1
Plane 2
Plane 3
Plane 4
Co
-203
1741
Rh
-239
1908
C(l)
8*
9*
C(2)
-15*
-17*
C(3)
14*
17*
C(4)
-8*
-9*
C(51)
-931
-1053
-7*
2*
C{b2)
-1211
-1307
15*
6*
C(j3)
-2043
-2168
-16*
-12*
C(54)
-2265
-2437
11*
13*
C(55)
-1598
-1774
-2*
-9*
P
1884
1922
3025
3241
59
(b) Coefficients of the Plane AX + BY + CZ = D
Plane A B C D
1
0.2201
0.0G27
0.9735
3.2807
2
0.2193
0.0672
0.9733
3.3160
3
0.7356
0.1345
0.6639
-0.8420
4
0.7474
0.1591
0.6450
-1.0481
^The entries marked with an asterisk were used to define
the plane.
131
ence could be indicative of multiple bonding between the ter-
minal carbon atoms of the diene and the metal atom. The C-C
distances in the metallocycle rings fall into tv/o groups. The
C(l)-C(2) and C(3)-C(4) distances are equal within experimen-
tal error to the accepted value of 1.337(6) h for a simple
C-C double bond. The C(2)-C(3) distances are indicative of
a C-C single bond between tv.-o double bonds. The observa-
tions of Mague ' on tvi/o rhodacycles suggested a double-
bond system similar to those in C^ (fph) ^Co (cp) (tpp) and C^
(fph)4Rh(cp) (tpp) .
The cp rings in the compounds arc planar v;ith the maxi-
mum deviations from the least-squares planes of -0.016
o
and -0.012 A. The distances from the cp ring atoms to the
metal atom shov/ that the metal atom is slightly displaced
from the center of the cp ring. The range of the Co-C(cp ring)
distances is from 2.104(9) to 2.157(12) A v;ith a mean of 2.127
o
(9) A. These values are similar to those in other Co-cp
complexes. ^05,106
In both the cobalt and rhodium compounds the longest
metal-C(cp ring) distance involves C(51), the carbon atom
nearest the phosphine ligand. The mean Rh-C(cp ring) distance
o
is 2.286(13) A. This value is equivalent to the mean distance
of 2.246(9) A in Rh (C2F5) (cp) I (CO) "^^"^ and falls within the
o
2.19 to 2.26 A range reported for corresponding mean values
for other cp- rhodium complexes.
The C--C bond distances v/ithin the cp rings range from
1.400(16) to 1.463(20) A with a mean of 1.436(11) A in the
132
cobalt, compound and a range from 1.420(17) to 1.431(18) A
o
with a mean of 1.4 25 A in the rhodium compound. These C-C
distances are comparable to those found in other cp com-
plexes. ' The cp rings are tipped relative to the
C(l) to C(4) planes by 35.3^ and 36.6°.
o
The Co-P distance of 2.234(3) A is similar to the Co-P
distance in five-coordinate complexes of cobalt where the
no ^
range is reported " to be from 2.152(G) to 2.27(1) A. Also,
in cobalt-carbonyl complexes such as Co^ (CO) •■ « (Ph2PCiCCB'2) 2
and Co(CO) -;,(N0) (tpp) the Co-P distances are 2,236 and 2.229
A-'--'--' Jn the former and 2.224(3) and 2.230(3) A-*"""-^ in the lat-
ter. The Rli-P distance of 2.293(3) A is similar to those in
113
phosphine complexes of rhodiura(I) . ' The metal to phosphine
distance in metal-oxime complexes have been found to be some-
40 97
v/hat longer, ' The Co-P distance in cobaloximc complexes
has been reported as 2.327(4) h^^ and 2.339(1) A.^^ The PJi-P
° 102
distance in RliC-£<Hd!ng) 2 (tpp) was reported to be 2.327(1) A.
Since the distances in oxime comj:>loxes in both cobalt and
rhodium are equivalent, the phosphorus atom may be in the
position of closest approach to the metal atom as limited by
the steric constraints of the oxime ligands.
The distances in the fph rings have been summarized in
Table 35. The individual values for the distances and angles
in the fph rings on the metallocycles and the phenyl rings of
the phosphides are given in Tables 36-38. The dimensions are
not unusual and are in agreement with expected values.
133
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134
Table 36
Bond Distances and Bond Angles of Pentaf luorophenyl Groups
in C^ (fph)^Rh(cp) (tpp) .
o
(a) Distances (A)
n = 1 2 3 4
Cnl-Cn2 1.384(15) 1.342(16) 1.392(15) 1.385(15)
Cn2-Cn3 1.364(20) 1.400(20) 1.374(20) 1.351(20)
Cn3-Cn4 1.375(18) 1.358(18) 1.357(19) 1.389(18)
Cn4-Cn5 1.367(19) 1.365(20) 1.368(18) 1.355(19)
Cn5-Cn6 X. 372(20) 1.373(19) 1.367(18) 1.362(19)
CnC-Cnl 1.393(15) 1.389(14) 1.389(16) 1.386(14)
Cn2-Fn2 1.347(12) 1.354(12) 1.351(13) 1.344(12)
Cn3-Fn3 1.339(15) 1.341(18) 1.349(15) 1.348(16)
Cn4-Fn4 1.338(18) 1.337(19) 1.335(18) 1.340(18)
Cn5-Fn5 1.343(15) 1.358(14) 1.338(15) 1.357(14)
Cn6-Fn6 1.331(13) 1.343(14) 1.351(13) 1.342(13)
(b) Angles (°)
Cnl-Cn2-Cn3 123.1(11) 122.4(12) 123.7(11) 122.9(11)
Cn2-Cn3-Cn4 119.6(13) 119.3(13) 113.8(13) 120.2(13)
Cn3-Cn4-Cn5 119.6(13) 119.3(14) 120.8(13) 117.9(13)
Cn4-Cn5-Cn6 119.8(13) 120.6(13) 119.0(12) 121.4(12)
Cn5-Cn6-Cnl 122.6(12) 121.1(11) 123.6(11) 122.0(11)
Cn6-Cnl-Cn2 115.3(11) 117.3(11) 114.1(10) 115.4(10)
Cn -Cnl-Cn2 124.2(10) 123.9(10) 123.1(10) 124.1(10)
Cn -Cnl-Cn6 120.5(10) 118.8(10) 122.5(10) 120.5(10)
Fn2-Cn2-Cnl 120.2(10) 121.3(11) 118.2(10) 119.4(10)
Fn2-Cn2-Cn3 116.7(11) 116.4(11) 118.0(11) 117.7(11)
Fn3-Cn3-Cn2 120.9(12) 120.7(13) 120.3(12) 120.8(12)
Fn3-Cn3-Cn4 119.5(12) 120.0(13) 120.9(12) 119.0(12)
Fn4-Cn4-Cn3 120.7(13) 121.3(14) 119.9(13) 119.9(12)
Fn4-Cn4-Cn5 119.7(13) 119.4(13) 119.3(13) 122.1(13)
Fn5-Cn5-Cn4 120.9(13) 120.1(13) 119.6(12) 118.8(12)
135
Table 36 - continued
n = 1 2 3
Fn6-Cn6-Cn5 115.7(10) 118.3(11) 117.6(10) 117.2(9)
Fn6-Cn6-Cnl 120.4(10) 118.8(10) 118.5(10) 119.7(9)
136
Table 37
Bond Distances and Bond Angles of Pentaf luorophenyl Groups
in C^{fph)^Co(cp) (tpp) .
e
(a) Distances (A)
n = 1 2 3 4
Cnl-Cn2 1.387(14) 1.372(16) 1.394(14) 1.403(15)
Cn2-Cn3 1.388(19) 1.368(20) 1.398(19) 1.358(19)
Cn3-Cn4 1.387(17) 1.374(18) 1.370(18) 1.348(16)
Cn4-Cn5 1.382(17) 1.374(20) 1.372(18) 1.370(17)
Cn5-CnC 1.382(18) 1.363(13) 1.362(18) 1.384(17)
CnG-Cnl 1.385(14) 1.389(14) 1.408(15) 1.367(14)
Cn2-Fn2 1.322(11) 1.341(12) 1.339(13) 1.358(11)
Cn3-rn3 1.350(14) 1.338(17) 1.339(14) 1.338(14)
Cn4-Fn4 1.360(17) 1.339(19) 1.334(17) 1.335(16)
Cn5-Fn5 1.336(13) 1.354(13) 1.330(14) 1.361(13)
Cn6-Fn6 1.341(12) 1.355(13) 1.356(12) 1.348(12)
(b) Angles (°)
Cnl-Cn2-Cn3 122.4(11) 122.9(12) 123.4(11) 122.6(10)
Cn2-Cn3"Cn4 119.7(12) 119.2(13) 118.9(12) 120.5(12)
Cn3-Cn4-Cn5 119.6(12) 120.1(14) 120.2(13) 118.7(12)
Cn4-Cn5-Cn6 118.7(12) 119.0(12) 119.8(12) 120.4(11)
Cn5-Cn6-Cnl 123.9(11) 122.9(11) 123.8(11) 123.0(10)
Cn6-Cnl-Cn2 115.6(10) 116.0(10) 113.9(10) 114.5(10)
Cn -Cnl-Cn2 123.3(10) 123.8(10) 122.9(9) 124.2(9)
Cn -Cnl-Cn6 121.0(10) 120.2(10) 123.0(9) 121.3(9)
Fn2-Cn2-Cnl 121.4(10) 120.5(10) 119.1(10) 119.8(9)
Fn2-Cp2-Cn3 116.2(10) 116.6(11) 117.5(10) 117.7(10)
Fn3-Cn3-Cn3 120.4(11) 122,0(13) 119.9(11) 119.1(11)
Fn3-Cn3-Cn4 119.9(11) 118.8(13) 121.2(12) 120.4(11)
Fn4-Cn4-Cn3 120.0(12) 121.2(13) 118.9(12) 120.1(11)
Fn4-Cn4-Cn5 120.4(12) 113.7(13) 120.9(12) 121.2(11)
Fn5-Cn5-Cn4 119.7(11) 120.5(12) 119.9(12) 119.8(11)
Fn5-Cn5-Cn6 121.6(11) 120.5(12) 120.3(11) 119.8(10)
Table 37 - continued
n = 1 2 3
137
Fn5-Cn5-Cn6 119.4 (12) 119.3(12) 121.4(12) 119.8(11)
Fn6-Cn6-Cn5 117.7(11) 115.0(1.1) 117.6(11) 117.9(10)
Fn6-Cn6-Cnl 119.7(11) 119.9(10) 118.9(10) 120.1(10)
138
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The fluorinated mctallocycles resist thermal decomposi-
tion better than the hydrocarbon analogs. ' Enhanced ther-
mal stabilities have been observed in other highly fluorina-
114
ted metallocycles relative to their hydrocarbon analogs.
In the compounds of this study the triphenylphosphine ligand
and the four fph rings provide an effective shield for the two
double bonds in the metallocycles. Although the fluorine
atoms of the fph rings and the phenyl rings of the tpp were
omitted from Figure 10, the sterically hindered nature of the
metallocycle may easily be seen. The lack of a convenient
path for an attacking acetylene together v/ith the enhanced
thermal stability of the fluorinated derivatives may have
allowed the isolation of these intermediate metallocycles.
Metallocycles of cobalt and rhodium of the type presented
are reasonable intermediates in the catalyzed oligomerization
of acetylenes.
CHAPTER 7
CONCLUDING REMARKS
The structure of C^Co (H2dmg) (drag) (clan) shows the same
LIPS phenomenon as c£ Co (H^dtag) (dmg) (sulfa) /'^ These two com-
pounds exhibit the unusual feature of containing both neutral
and dianionic dimethylglyoxime groups. Also, the orientation
of the benzene ring of the sulfa and clan group in the respec-
tive compounds is over the dianionic dmg. The various dis-
tances and the relative orientation of the axial ligand in
both compounds suggest a n-type interaction. LIPS supports
the contention that "hydrophobic forces" are important in en-
zymic processes.^ The bis (diglyoxima to) cobalt (III) complexes
of aniline derivatives have here been shown to be useful mo-
dels for the examination of tliis type interaction. An exten-
sion of X-ray structural determinations to similar compounds
with other aniline derivatives and with other diglyoximes is
suggested. Low- temperature X-ray studies could effect better
resolution of the inter-drug bridge structure and the N-0
distances .
An investigation of the fluorescence spectra of these
compounds could reveal additional information concerning the
interaction between the equatorial and axial ligands. The
fluorescence of 5-dimethylaminonaphthalene-l-sulfonamide was
observed to be enhanced while the fluorescence of carbonic
141
142
anhydrasG was diminished when a 1:1 complex of the tv/o was
formed. "* Although the major contribution to this observa-
tion is believed to be the ionization of the sulfonamide, a
portion of the change is attributed to a hydrophobic inter-
action. -'■'■' ^^^ The fluorescence spectra of cobaloxime com-
plexes with aniline derivatives should help reveal tlie nature
of the interligand interaction as a function of the orienta-
tion angle.
The novel ligand dhphpy has been demonstrated as a bi-
nucleating ligand. The bridging site occupied by a chlorine
atom in [Ni2C£ (H2O) ^ (dhphpy) ] Cf^ clearly is accessible and
of convenient dimensions to accommodate a molecule such as
dinitrogen. Further development of this system as a possible
model for nitrogenase should include use of molybdenum salts
and work with the exclusion of oxygen. Synthesis of similar
ligands with saturated "side arms" is also suggested.
The compounds C^ (f ph) ^Co(cp) (tpp) and C^ (fph) ^Rh (cp) (tpp)
contain a butadiene fragment with each end bound to a metal
atom. The metal to carbon bonds are shorter than expected
for the single-bonded distance. The metallocycles are, there-
fore, believed to contain a delocalized Ti-bonding system.
While metallocycles should be higl;ly susceptible to nucleo-
philic attack and thermal decomposition the two compounds
studied here are very stable. The enhancement of thermal sta-
bility by the fluorinated substituents may be at least par-
tially responsible. Also, the presence of the four fph rings
143
along with the tpp and cp ligands provides a shield from
attack for the metallocycle.
The understanding of catalytic processes should improve
the efficiency of our existence. Hopefully, enzymic pro-
cesses occurring in nature can be duplicated in the labora-
tory by suitable models. These model enzyme systems may then
be applied to cure the diseased and feed the hungry.
APPENDIX A
BOOTH I Tl
A listing of the FORTRAN language computer program
BOOTHITl follows. This program was designed to interpolate
atomic positional parameters by Booth's method from the
values of a Fourier synthesis calculation. The Fourier syn-
thesis program v/ritten by Dr. Gus J. Palenik v;as modified to
store the calculated values on a magnetic disk. After supply-
ing BOOTHITl with input data of the approximate position of
each atom, the stored values are retrieved. The program esti-
mates the position of maximum electron density for each atom
from these Fourier synthesis values. The positional parame-
ters may be translated to equivalent positions and may be
passed to a bond distance and angle program. The resulting
fractional coordinates are punched into IBM cards in the for-
mat required for their input into the Fourier synthesis and
least-squares refinement programs.
144
145
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XX»-«~*'-<XXXktJJ
APPENDIX B
OBSERVED AND CALCULATED STRUCTURE FACTORS
Table B~l
Observed and Calculated Structure Factors for c£Co (H2dpg2) -
(clan) •C2H^0H
15C
FCI
rc
FC
FC
f c
FC
I O
FC
H=
19
-14 1
- 100
1 1
-136
70
2
-142
100
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0. K--
0
12
292
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3
-1 40
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13
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4
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3137
14
41 3
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-64
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174 9
1 72 4
15
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1
2 / 4 O -
2742
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27 1
2/6
7
2*i6
139
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4 (.< li
2
21 1
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8
-150
6V
1 c
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3
694
7 0O
H=
C, K =
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1 ^
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4
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14
63 0
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101
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0
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IC
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6
303
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1
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12
1
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18
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7
210
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2
265
2 03
2
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245
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3
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79
3
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12 1
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9
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4
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4
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10
20 7
3 7 I
f
439
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1
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239
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7
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207
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9
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19
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310
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339
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3
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192
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614
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c
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690
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17
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50
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160
3
16
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7
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390
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9
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067
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190
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670
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6
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1
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1364
c.
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46
1 r
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2
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72
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3
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4
1269
1259
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16 A
99
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0
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5
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16
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6
557
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10
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379
0
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2
216
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530
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154
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1 1
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31 4
-33o
-3
214
-151
-2
tiCt
fcl 7
- 7
- 130
- 1 o6
c
-136
9
-2
-1 '*3
-29
- 1
£^7
-te 1
-6
-l3o
l^^d
6
-136
19^
-1
-144
190
— t
-136
222
7
22 '3
-96
H=
12 . K
3
-4
-138
-10
e
- 140
-53
H-
12. K =
0
-3
271
-33 7
9
-143
-f.l
0
-138
139
-2
J69
-35 1
10
-149
6
0
94 7
991
1
2 12
- 179
- 1
356
257
-13
-14.^
- 1C3
2
-133
- 1 34
2
-141
-79
-12
-143
6 3
4
- 130
333
3
-136
-30
h =
12, K^
- 6
-1 1
-13b
-3
6
2ij0
-218
4
-135
5 7
-10
-i3o
-58
S
- 1 3 /
3
C.
-137
-101
0
-135
-72
-9
-13tl
ao
10
-143
1 86
t
- 1 33
-4 1
1
390
397
-0
-134
35
12
294
- Jb7
7
192
4 6
2
-135
-126
-7
-13£
-67
-14
-1 Jt.
43
8
-13o
-61
3
207
-195
-6
21 1
-131
-12
195
13/
9
-135
-9
4
-130
141
-5
-131
-41
-10
-120
-1
10
- 139
lo
5
-14 1
30
-4
-136
179
-8
-135
- 158
1 I
- 146
- 162
fc
289
-153
-3
-ijy
-12a
-6
-131
j-9
-14
- 1 tt*
-119
7
-147
1 I d
-2
3Z'o
291
-4
3t30
3o9
- 13
2C3
173
8
-148
-66
-1
-137
-53
"" £.
1112 -
1 C95
- I <
- 134
3
-12
-143
-10
- \ 1
- i3e
-o
-11
-139
-Ol
H=
11. K-
7
h-
12, K^
1
-1 0
-129
7d
-1 0
-140
1 1
-9
3C9
-2 73
-9
214
203
0
263
256
0
-130
104
-8
- 1 3 9
-153
-e
2Co
-1^^3
1
-137
170
1
-131
-o2
-7
3 17
3 37
-7
-139
0
2
i'90
-3CC
2
-131
4 9
-o
- 137
1 74
-6
-14 5
2o5
3
-139
5
3
2'.y
207
-b
-136
-2C7
• c:
-134
-154
4
-137
145
4
-130
-loi
- 1*
2 to
-2cl
-4
-134
32
S
-140
-124
5
-loo
1 12
-3
42 1
423
-3
-137
36
171
FC
PC
FO
rc
FC
FC
FO
FC
-2
192
73
H=
13, K:
0
c
-134
-177
2
-135
-4 1
- 1
304
-2o3
t>
-I 39
-16
3
-1 '^O
-20
1
-135
-86
7
2 59
292
4
• 195
124
H-
12. K =
7
3
202
96
a
- 136
-51
5
230
- 13
5
-135
16/
9
223
- 156
e
-14 1
-206
0
193
128
7
207
- 190
10
-l/!3
46
7
-14 1
-7 7
1
200
-106
9
^l^
160
-13
-136
1 lb
e
-I4'i
1 2 5
2
-143
127
-13
~l 40
32
- 12
- ) '! 3
- 12o
9
- 1 4 3
4 6
2
205
135
-1 I
-13o
38
- 1 1
190
- 16o
-12
-145
100
A
-142
-67
-9
-134
-lOo
-10
-133
187
- 1 1
-140
4 4
t
-1 '';3
-46
-7
-134
0
-9
- 13t
9 9
-IC
-140
-153
0
- 1 4 t.
141
-5
-13i1
36
-8
-136
-150
-9
264
204
7
-14 c.
- l<^
-3
6d3
-674
-7
-134
99
-e
-136
7 J
-10
- 1 A 4
7
-1
430
44 2
-6
- i;c
39
-7
194
-20
-9
-147
- lf'4
-5
390
-3 7 0
-6
-133
154
-e
-14 0
17
V =
13. K:
1
-4
233
143
-5
-140
-245
-7
2 00
270
_ -a
ece
£52
-4
400
-404
-6
-1 4 C
- 1 CO
0
-132
- 139
-2
344
-286
-3
230
106
-5
-143
-109
1
-133
1 17
-1
-138
-173
-2
4C6
42d
-4
-130
144
2
-130
65
- 1
2fcti
195
_ a
201
164
3
265
-2 64
H=
i;. K=
3
-2
-134
- 1 0?
4
-135
19
1 -
13, K:
= 5
-1
-137
-72
5
2 9 is
294
0
202
-223
6
-136
- 179
1
- 1 3 3
- 117
0
-135
-99
h-
12. K=
O
7
-135
-12b
2
-137
150
1
-139
-143
8
209
1 1 1
^
-136
29
2
-135
54
0
2S8
-195
9
- I3a
24
4
2? t
-249
3
- 136
153
1
232
- 135
10
- 1. 4 6
-37
5
- 134
-74
4
24 0
223
2
-14 7
6 3
-14
- I 46
-83
C
213
246
5
-138
-60
3
- 14 1
28
-13
-139
5 5
7
-14C
- 16C
e
290
-29G
A
-14 4
-42
-12
-139
1 06
a
- 14 1
t5
7
-14 3
1 1 1
5
- l£<0
171
-1 1
-136
- 19b
9
- 1 4 4
64
8
257
99
-8
2e>'.-
14 3.
-10
-133
-16
-13
-138
-33
- I 1
-142
-1.^
-7
- 144
- 1 0 n
-9
266
296
- i:?
- K^9
123
-10
-14 1
149
-C
-143
2tJ
-0
-130
-6
-1 1
-1^1
109
-9
-140
66
-s
-140
144
-7
-130
-1 lo
- 10
- 1 3 9
-137
-8
- !43
- 2 6 4
-4
-14')
-194
-6
-132
-2
-9
' *" 3
-289
-7
-l'i2
6 0
-3
27 0
-10?
~r>
271
1 6 9
-8
-135
210
-6
3 1 a
2<J3
-2
- 1 ■'. 8
195
-4
21 a
-310
-7
- i:-c
ii;2
^ c
-134
121
-1
25 3
lt)4
-3
2 56
- 2 57
-C
240
-2 74
-4
2'Jl
-22 1
-2
220
270
— 5
4 JO
-4 17
-3
-136
-207
H=
1 2» K=
9
-1
277
-156
-4
- 1 3 5
69
— 2
-135
l-'fO
» -a
547
52 5
_ 1
315
28 7
0
-1 L,!
55
M =
13. K
2
-2
- 143
273
1
-145
-74
-I
-13G
-252
I =
13. r.'
6
-4
-l£.l
-90
0
210
78
* Ti
- 1 4 4
-90
1
226
- 193
, H==:
13 . K
- 4
-10
-142
16
-2
-IbO
28
?
-13!
-64
-9
-141
-123
-1
-14o
81
3
-136
2 9
0
21 0
-24 8
-e
-143
39
4
-132
89
1
- ic-e
-15
Table B-2
Observed and Calculated Structure Factors for [Co(Hdnig)2-
(clan)2]c£
173
FO
FC
FO
f C
FO
rc
FO
FC
0
155
-142
H=
0. K-
6
6
15
-6
K=
0, K =
0
I
1 3^
-126
7
ZM^
230
2
40
35
0
26 2
263
8
24 1
2 54
1
76S
730
3
95
-bC
1
371
379
9
64
62
?
0O9
'.2 0
4
28
30
2
2 99
29 5
10
229
234
3
I J7
1?1
5
1 18
-1 13
3
?.'.'(
258
1 1
12to
131
4
202
177
6
295
270
4
195
197
12
19/
199
S
43V
<0t5
7
1 5 0
137
5
128
131
-1 3
122
128
6
4B
3 b
B
1 30
131
6
172
172
-12
42
4 1
7
35 7
34 2
9
lt;4
184
7
4 3
4 4
-1 1
147
155
6
75
73
10
60
l> 1
8
70
74
-10
1 9 5
194
9
229
210
1 1
95
95
9
68
63
-9
1 1 1
11 0
10
•JiJ
r.e
12
-12
-10
- 10
131
13o
-8
385
367
11
;;30
2?9
~l 2
OCJ
69
-9
92
91
-7
231
22 3
12
103
lOE
- t 1
-12
- 16
-«
101
99
-6
414
384
13
43
39
-10
42
-44
-7
75
70
-5
24
25
_o
135
133
— 6
140
141
- 4
31 1
3C0
H =
Ct r-
1
-G
I 17
15 7
-5
206
2 04
-3
30
~z\
--7
1 I 0
113
-4
178
1 78
-2
4 3
4 5
0
6t>l
636
-6
15
23
-3
2 28
228
-1
653
62 7
1
42t>
400
-5
23 '►
233
~2
1 90
188
2
34!>
3C9
-4
173
163
-1
1 85
189
h-
1 . K=
1
3
17 :■
If.'.
-3
41
2 9
4
235
-217
-2
304
-292
H=
Ot K-
7
0
238
-229
5
172
161
-1
239
-225
1
99
94
6
31S
-270
0
76
78
2
315
-301
7
226
191
H-
0. K:
4
1
27
28
3
1 10
-1 15
e
101
105
2
59
56
4
343
330
9
6C
54
0
21 1
199
3
124
123
5
72
-6 1
10
190
193
1
104
191
4
97
100
6
223
217
1 1
ai
83
2
333
332
5
54
46
7
34
3 2
12
17''.
177
3
23 b
224
6
-1 1
0
8
2 87
281
13
2/
P!
4
202
201
7
32
37
9
-11
1 1
-13
53
:,7
5
32t4
32 9
8
1 10
11 2
10
127
127
-12
44
-48
6
132
131
-9
-12
2
1 1
1/
3 2
-11
10 I
103
7
204
199
-3
- 1 1
10
12
-12
-4
-10
-I A
15
8
6 0
67
-7
-1 1
-2
-13
-12
14
-9
67
-6?
9
138
13o
-6
-1 1
-7
-12
6 0
60
~S
-12
-8
1 0
60
58
-5
69
68
-11
100
99
~7
31
1
1 1
132
137
-4
214
21 1
-10
144
1^8
-6
S&5
51 9
-12
104
107
-3
242
247
-9
175
-173
-5
231
216
-1 1
104
105
-2
126
128
-8
166
177
-4
349
337
-10
146
147
- 1
CI
64
-7
55
53
-3
103
- 103
-9
224
230
-6
88
69
-2
G4
-73
-8
75
7<3
H=
0. K--
8
-5
le4
-164
-1
443
431
-7
194
190
-4
399
-370
-6
160
Ibb
0
104
11 1
"• 3
285
292
H=
Ot K-
2
-5
210
214
1
67
66
-2
176
-174
-4
2b3
205
2
93
99
-1
426
421
0
475
-471
-3
31
30
3
1 I 1
112
1
394
367
-2
21
19
4
1 03
lOu
h-
1 . K::
2
2
299
279
-I
1 12
-102
*;
54
97
3
20''
IHK
6
VO
90
0
413
39 4
4
14c.
13 1
H=
0, K=
5
-7
83
83
1
59
53
5
40
-36
-6
£1
62
2
41 1
392
6
4f-7
.'■6 4
0
-1 0
a
-5
7 9
78
3
fcl
85
7
2C9
256
1
271
26 6
-4
193
1^4
4
28 4
260
e
3^0
303
2
193
190
-3
2C0
282
5
37
38
9
1 1 5
1 14
3
89
9 4
« >
2 73
.'iV6
6
241
225
10
297
291
4
58
54
-1
192
193
-?
194
lud
11
74
78
5
138
140
0
213
2 '04
12
91
67
6
93
91
H=
C. K-
9
9
322
323
-13
34
38
7
21
28
10
81
79
-12
52
47
P
59
-61
0
-11
5
1 1
70
7?
-11
36
38
Q
51
-49
1
-1 1
17
12
78
-78
-10
102
IC3
10
28
26
2
26
30
-13
74
7 4
-9
-1 4
21
-1 1
92
94
_3
26
24
-12
145
151
-8
23B
24 1
-IC
195
196
-2
45
45
- 1 I
1 1 0
1 13
-7
67
73
-9
90
93
- 1
26
29
-10
ZA
-27
-6
4t'6
472
-0
16
-9
-9
146
l«4
-5
547
51 2
-7
20
-16
H-
1. K =
0
-a
126
132
-4
476
iii-O
-6
61
6 0
-7
269
266
-3
4 0U
4 50
-5
60
5 3
0
1-99
676
-6
1 AO
I -13
-2
2 3b
228
-4
34
-30
1
2^0
2«2
-5
159
11,0
-1
67 3
660
-3
73
-72
2
4b
40
-4
44
-37
-2
36
4 2
3
671
651
-3
306
323
H =
0, K-
3
-1
25
- 19
4
337
324
-2
300
2 9t>
C
£2C
491
-1
302
2 'J 4
174
FO
FC
FO
fC
ro
rc
i (I
rc
-6
127
135
H-
1 , r
= 3
H =
1 . K=
6
— 5
175
175
0
24 4
232
-4
ia3
1 »■ 7
1
•1 til
106
0
1S{.
159
0
22 1
225
-3
1 66
173
2
3'.-)
3c) 4
1
23/
- .'. 3 1
1
: '^4
KI2
- 2
1 C4
1C7
3
'.J I
4 --•7
2
1 46
140
2
166
lo6
-1
63
65
4
1<;4
)i.6
3
.-<t7
23 9
3
176
172
5
1 ](>
1 19
4
33
3 7
4
Itttt
rV7
H=
1 . K =
-7
6
1 t 3
195
5
130
127
5
244
233
7
1//
lOJ
6
1' C
-14?
6
i;4
151
0
22
24
8
1 1 1
1 13
1
IS 7
IbD
7
37
34
1
30
33
9
12c.
1 17
a
- I 1
-1 2
8
102
lO-i
2
63
6 3
10
75
60
9
l^O
J 23
-10
105
104
3
107
107
1 1
2 2
26
10
<>6
68
-o
72
69
4
33
2 9
- 12
105
109
1 1
-1 1
9
-8
30
26
5
16
- 12
-1 I
1 1 4
1 15
- 13
'Jt,
99
-7
1 13
1 10
6
38
42
-10
71
7 5
- 1 i:
10 1
10?
-6
2c.0
25?
7
100
1 C :•■.
-9
170
168
-I 1
- 1 I
10
-5
309
314
e
99
104
-8
133
134
-1 0
1 OH
-1 09
-4
246
240
-t
93
93
-7
-1 1
-2
-9
1 J-<
137
-3
1 tt,
175
-7
41
42
-6
262
251
-e
t>0
47
-2
160
150
-6
40
35
-5
24 5
229
-7
9f.
96
-1
152
15tJ
-5
36
35
-4
350
334
-6
-1 0
15
— A
C2
66
-3
2 14
20 7
-r.
2 0
?fi
h=
1. K =
7
-3
45
40
-2
194
193
-<.
2e.7
249
-2
46
-4?
- 1
3i:i
380
-3
13 1
- 132
P
53
59
- 1
22
-11
-2
1 t16
17«
1
16
- 14
H-
1 . i;=
-3
- 1
loj
177
2
- 1 )
- 5
H=
1 . K=
-6
3
4/
47
0
629
-617
H-
1 . K
= 4
4
52
52
0
134
14 1
1
7 1
66
c
56
58
1
22 9
225
2
198
192
0
29 H
295
C
- 12
0
2
24 2
24 3
3
37 5
361
I
AO-.
400
7
93
10 1
3
1(5
165
4
314
297
2
23 J
2 30
-9
-12
15
4
124
12/
5
59
-53
3
294
204
-a
-12
-1 7
5
120
I'- 5
6
70
6 7
<(
246
24 4
-7
30
-28
fc
9r
10 1
7
3o
36
6
20U
203
-6
22
-20
7
1 13
1 1 4
8
1C9
162
6
K.2
13<:
-f.
36
35
P
1 12
11 1
9
-1 1
3
7
1 1 3
1 10
-4
79
80
9
62
t.b
1 0
- J J
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- 13
39
40
-6
136
14 3
-1
1 1 0
1 17
-10
6J
55
- 12
- 12
15
-5
134
133
-9
57
57
- 1 1
47
-4C
-4
63
60
1-
3. K=
-7
-8
4 9
39
-i 0
1 69
161
-3
3 8---
3 70
-7
1 2fJ
J 27
.- CJ
-1 1
2
-2
247
25 1
0
3 5
32
-6
1 52
14a
-e
66
6 5
-I
206
204
1
2 7
26
-5
157
164
-7
104
102
2
33
?,7
--4
63
60
- fc
196 .
100
H=
4. K-
3
3
46
45
-3
1 0 9
105
~5
3 76
365
4
-1 1
1
-2
343
3 38
-4
112 •
■- 1 I 4
0
- J 0
-6
b
-1 1
G
-1
3/-£)
303
-3
156
155
1
107 ■
-100
6
26
7 1
-2
168
165
2
2 7
-26
-e
I'j/
If 6
H=
3. K-
-3
- I
150
153
3
17
-14
-7
115
125
4
25
19
-6
. 17
14
0
197
202
H=
4. K-
0
5
9]
90
-5
-1 1
. 0
1
9?
9 4
6
- 1 I
14
-4
41
4 0
2
142
146
0
219
212
-1 1
32
32
-3
125
12H
3
263
2 54
1
231
234
-10
36
-4 1
-2
132
US
4
2ii
29
2
200
2 0ci
-9
33
30
-1
2<J
22
5
2 5
21
3
402
39 8
-a
19
-9
6
3o
-30
4
205
205
-7
39
37
1-
3, !;=
-6
7
62
6 2
5
4 1 1
4 25
-6
-1 I
24
8
62
62
6
124
12o
-5
63
-62
0
2ft3
28f.
9
136
143
7
49
60
-4
153
166
1
169
100
10
124
1 19
C
107
108
-3
228
23 1
?.
MA
'.45
-12
103
99
-12
1 50
156
-2
21 2
214
3
17 3
171
~\ \
4 6
4 9
- 1 1
ito
17 8
-I
61
61
4
iQ-y
196
-10
1 J3
- 125
- 10
136
144
c.
If- 6
ir7
-9
2 3
14
-9
165
159
h=
4, K-
4
6
70
6 0
-8
19
-15
-6
1 22
129
7
9 0
a?
-7
- I 0
19
-7
1 10
105
0
1 22
123
■10
97
104
-6
32
-24
-6
247
■d^!i
1
4 'J
4 6
-<.!
167
1 f^g
-5
71
-72
— C
143
141
2
1 09
-1 15
-8
300
3 0'*-
-4
1 C8
1 14
- 4
?( ?-
26 2
3
3 7
13
-7
277
2H1
- 3
32
-29
"■ 3
\ 59
158
4
4 3
Za
-6
215
217
- 2
145
132
-2
322
317
5
1 13
1 ! 7
-5
i;its
13<i
-1
103
102
-1
204
199
-10
5o
55
-4
133
128
-9
137
139
-3
1^.5
1^6
H=
3, K-
-2
\\-
4, K=
1
-a
177
1/6
-2
6^
57
-7
147
146
-1
ICb
161
0
3 6
39
0
181
178
-6
102
94
1
206
2C2
J
1 83
leo
-5
102
96
1 =
3. K =
-5
2
152
143
2
l':2
144
-4
228
226
3
292
307
3
220
221
-3
85
6-:
0
96
9R
4
2/6
273
4
2L4
265
-2
190
169
1
74
75
5
196
201
5
1 CO
100
-1
256
2-39
2
66
86
6
55
44
6
- 1 1
5
3
104
104
7
30
-23
7
- 1 1
0
H=
4. K=
5
4
217
2?0
a
82
76
a
1 ! 0
I 14
5
130
131
9
62
63
- 1?
63
68
0
85
8V
6
,60
58
10
120
122
- 1 1
79
74
1
-1 1
17
7
53
50
-13
1 1 /
1 1 7
- 10
126
130
2
57
-62
6
84
81
-12
9 3
93
-9
-1 1
3
3
22
19
■1 1
64
6 5
-1 3
31
-33
-8
90
90
4
6 2
61
•10
68
6 7
-10
86
91
-7
-10
4
-9
4 7
4 5
— 9
-1 1
10
-g
4 6
44
-6
- 10
-2
-3
67
80
-6
77
Ti
-8
143
138
— 1_>
--10
4
-7
109
1 13
-7
131
13?
-7
I 3(->
131
-4
70
-72
-6
91
91
-6
190
ise
-A
212
221
-3
91
54
-5
1 lO
1 15
-5
1 04
104
_e-,
242
233
-2
10/
105
-4
- 1 1
- 1 7
-4
-10
0
-4
362
354
-1
312
315
-3
78
-G 1
-3
32
-2 3
-3
270
263
-2
-1 1
-7
-2
42
-36
-2
216
214
H =
4, K=
2
- 1
84
85
-1
17b
171
-1
290
2 75
0
196
201
H-
4t K-
6
1=
3, K^
-4
h-
3. K=
-1
1
137
135
2
290
2 93
0
145
146
0
266
256
0
192
- 186
3
Its
167
1
1 1 1
109
1
214
210
1
47
-33
4
293
296
2
14t>
140
2
264
271
2
47
-50
5
-1 1
10
-7
1-^9
151
3
253
250
3
123
-110
6
47
46
-t
175
177
178
ru
FC
FO
FC
HO
FC
f O
FC
», «,
127
133
5
- I 1
- 14
-O
92
91
-7
-1 1
-6
-A
-J?
lb
6
-I 1
3
-7
1 '^l
184
-6
48
-58
-:i
f.I
4 7
I
82
06
-6
195
196
-5
IOC
-99
-?
£1 y
84
-1 1
11 V
1 19
-5
lo6
163
-4
133
129
- 1
1 1 0
1 1 1
-10
37
39
-4
10 >
102
-3
131
134
-9
103
101
-3
1 2 1
1 19
-2
86
04
n=
4, K-
-b
-n-
9 7
98
-2
1 ti :>
1H2
-1
39
35
-7
129
127
- 1
If 6 ■
- 169
0
S?
0 0
-6
149
14r3
H-
5. K =
4
1
121
12 1
— «■,
68
71
M =
E. K =
0
— 1>
U'J
<11
-A
149
149
0
125
132
-A,
I l<i
121
-3
1 40
140
0
174
173
1
120
1 19
-3
17f.
r/q
-7
1 71
170
1
223
227
2
04
9b
-2
179
182
-I
lo9
181
2
17:>
1 74
-8
108
1 13
-1
8t>
BO
3
li3
84
-7
62
69
F =
■< , K =
-3
4
93
93
-6
34
29
H-
A , »■-:-
-7
5
94
102
-5
123
124
0
VO
-65
6
125
12o
-4
152
149
0
^,<)
4P
I
1 7
12
-1 I
-12
14
-3
1 o5
lt>3
1
tt'
fi9
2
122
123
- 10
l<.o
147
-2
16b
167
2
1 1 2
1 1 4
3
1 17
12 2
-9
1 1 1
1 16
-1
lo3
164
3
eo
7h
4
-1 1
-20
-8
144
144
A
b6
53
&
Ibl
-146
-7
119
124
1-' =
5. K=
5
-V
b9
66
6
6«
-76
-6
200
191
-t.
30
29
7
49
53
-5
319
321
-6
23
30
-5
A?
40
8
99
100
— 4
123
12 0
-5
54
56
-/f
59
61
-1 2
OS
87
-3
t;7
87
-4
61
62
-3
76
77
-1 1
2 b
-25
-2
95
92
-3
69
89
-2
2f.
20
-10
17
19
-1
163
ia4
-2
9b
9t.
-1
-1 1
-3
-9
69
66
- I
1 r,7
105
-O
125
127
H=
5. K-
1
H-
A , K-
-6
-7
57
59
H =
5, K=
-7
-6
-I I
5
0
22
1 1
0
1C7
lf<P
-5
ICl
102
1
-.1 1
-3
0
24
-20
1
IVO
17 1
-4
??0
224.
2
180
165
1
28
-^2
2
1 '- ;;
154
-3
I 06
103
3
£1
79
-5
82
83
3
isj
154
-2
20
-20
4
9C
94
-4
96
99
C
200
U^O
-\
71
71
5
-11
-8
-3
1 '^..
1 "3
5
J 73
1 /5
-1 I
3S
48
-2
89
90
6
1 <. V
152
n-
4 , K=
-2
-10
£5
54
- I
44
42
-9
103
109
-9
32
34
-0
120
l?-S
0
76
-71
-8
27
27
H=
5. K=
-6
-7
101
104
I
•49
53
-7
59
60
-6
104
105
2
203
202
-6
133
13b
0
1 1 1
1 12
-5
144
147
3
172
174
-5
221
21 b
1
Z.i
33
-A
171
168
4
210
2C»
-4
29
-17
2
25
-20
-3
147
I4ft
5
38
-4C
-3
29
23
3
-12
15
-2
64
07
6
124
127
-2
73
-t.8
-7
93
92
-1
156
156
7
1 44
142
-1
100 -
-10b
-6
1 15
117
8
135
142
-5
1 15
lis
H-
A, K.=
_^
-12
64
e3
H =
5. K-
2
-4
91
90
-1 1
-1 I
> I
-3
107
lOd
0
l»5
18t>
-10
1 « J
140
0
-1 I
2
-2
1 4t>
Ibl
1
16:'
16S
-O
1 79
1<?8
1
CO
62
- 1
147
150
2
b/
SD
-8
266
2^4
2
15 I
1S4
3
-1 I
4
-7
262
267
3
122
126
n=
5, K =
-5
4
jb
33
-6
143
l4^
4
72
77
b
4 a
44
-5
335
ZZ-ii
5
131
128
0
136
138
6
6 c
64
-4
282
ZTQ
- 10
1 16
1 17
1
70
t,7
7
9 3
6P
-3
332
324
-9
1 17
1 16
2
Ab
-48
-10
44
4 3
-2
199
190
- 3
70
72
3
45
-46
-9
- I?.
6
-1
09
93
-7
90
82
4
Z^
19
-8
-1 1
-4
-6
1 13
117
-9
52
53
-7
20
IB
H=
*. K =
-1
-5
25
22
-8
59
57
-6
20
21
-4
203
21 1
-7
107
1 06
-5
26
-23
0
73
-t-5
-3
246
247
-6
106
106
-4
21
-19
1
23
?2
-2
107
1C6
-5
-1 1
-16
-3
43
4 3
2
1 :^b
163
-I
51
-47
-*
43
-bO
-2
b7
87
3
Id3
174
-3
■ 4b
-4 4
-1
1 IC-
1 1 3
4
c»V
1 iO
H =
5. K-
3
-2
3^
-33
5
176
170
-1
41
39
H-
4, K =
-4
6
140
149
0
31
-3b
7
63
t>.»
1
1 10
1 I 1
hi-=
5. K=
-4
0
2t.7
26 8
8
37
42
2
26
20
1
271
27li
-1 2
4t>
45
3
51
45
0
210
214
2
227
23A
-1 1
47
52
4
36
3-i
1
169
1 t<8
3
132
127
-10
21
19
-S
Sb
94
2
1 29
Ko
A
Ab
-40
-9
121
129
-8
64
61
3
57
62
379
L
PO
rc
L
ru
FC
L
ro
FC
<
1 Hi
1 1 2
-5
2ie
221
-7
2 3
2 5
5
1 19
122
-4
307
30 8
-6
1 4 6
1 5 3
- 10
16 V
J f. 9
-3
223
22 5
- 5
7 0
6 7
-y
1^9
J. -^4
-?
216
219
-4
17
1
-U
ip-y
129
-1
165
J 65
~3
P.3
"2 7
-7
ion
]Oft
-2
"1 1
6
-U
l^ti
149
H-
5, K.-r
-1
- 1
~ ',
33
-b
9ii
9 7
-4
OA.
6 2
0
1 2b
132
H---
6 , K.=
2
-3
3 0
31
1
215
21 3
-2
27-
2 7
2
73
71
0
1 2 7
1 2 7
-1
172
16 9
3
75
77
1
2 16
219
4
21
-30
-7
80
0 5
H-
r.. K=
— 1
5
140
14 5
-6
120
1 1^
6
10';
102
-5
7?
7o
0
lAl
139
-1 1
-12
5
-4
1 4 9
146
1
136
1 3P
-10
20
17
— ">
12/
1 :r)
2
iby
160
-9
25
25
-2
1 0 ■■;
102
3
6>1
(M
-c
-1 1
15
- 1
1 4^
1 -. y
A
71
7?
-7
25
I«
5
y<i
-31
-6
91
92
H-
6 , K.=
3
C
a?.
fi3
-ft
1 14
116
-1 I
'iS
<5 P
-•4
257
25';
— *">
«4
05
-10
79
75
-3
139
140
-4
1 00
100
-9
hi
H^.
-2
127
127
- 3
142
137
-e
'oG
07
-1
tJ4
as
-2
94
95
-7
'^U
61
-6
30
23
H=
6, K-
0
t;-=:
C t K.-
— li
-5
1 I 0
1 I 0
-^
A'^
4 5
0
I 1 I
1 16
0
98
100
-3
If.
3
1
35
36
-6
44
4 6
-2
43
3C
2
1 05
10*3
- 5
- ) 1
6
-1
ISG
167
-5
95
94
-4
26
2 0
-9
64
6:'.
-3
54
52
H-
5. K=:
-2
-G
BO
B2
"2
5 7
5 7
-7
151
147
-1
95
9 4
0
2^6
24 0
-6
2 16
2<i2
1
r7o
265
23 a
23 Li
ri ^
c. i;-^
■"4
2
224
233
-4
33
-33
3
202
197
-3
52
-55
0
IPS
186
A
60
ec
-2
20
19
1
139
1 3 V
5
5^
5 2
-1
44
43
2
1 J5
1 17
6
136
l'. 4
-«
i::-5
12S
-I I
71
7 '3
H-
6t K=;
1
-7
160
165
-10
-1 2
2 5
-6
140
l';7
-9
98
90
0
40
37
-5
1 01
104
-e
1 1 1
1 10
1
29
30
-4
69
72
-7
134
134
2
06
92
-3
1 J3
13<
-6
lb7
160
-8
-11
-9
-2
162
lti5
H--
L
ro
FC
- 1
210
215
-
o . r.=
-3
0
.5 0
tt3
1
07
6 5
4.,
74
7 8
3
9/
96
- 9
32
29
■C
4 2
4 7
- 7
7 0
71
-6
tiO
91
-5
4 0
4 3
-4
f.2
63
-3
) 30
130
-2
1 76
1/6
- 1
1 47
147
6 . K=:
-2
0
126
130
1
93
92
r*
3!
29
3
76
79
-9
98
97
-0
1 35
135
•7
1 16
122
-6
6i
6 1
- 5
4 9
55
4
2C6
20 3
•3
Jti3
104
•2
ie9
194
■i
201
204
6, K=--
-I
0
94
92
1
^•r)
j9
2
20
-3?.
3
17
-16
9
50
51
■8
1 15
1 13
7
11 1
1 34
6
20
17
. c.
6 5
66
4
- 1 1
-1 I
3
45
-49
2
15
2
Table B-3
Observed and Calculated Structure Factors for H^dhphpy (NO^) ^
181
n=
e
e
10
h--
0
6
e
10
0
2
.4
6
e
10
1-:=
C
?.
A
6
e
10
H=
0
p.
6
H=
H-
PO
0, K
32 1
1 01;
>: 9 2
37
2, K =
PA 7
26
9f.
73
FC
3?3
- !C0
?63
-?ft2
0
-?'i 1
???
??
77
K-
C
e
e
0
6
3M
130
?6
1C.9
0 9
6,
b31
13 1
-J 8
SB
-22
e. K
29 0
6;.-
<5u3
&0
AC
- :?q7
3i".
- I r:.c.
sets
i;=
10:
K =
0 b't
2 3?/j
4 239
6 Ab
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33
16
-9t>
-6
-15
30
- 14
45
-50
33
13. K-
H=
0
-22
-13
1
40
36
13. K=
9
1
-22
34
2
-22
27
3
-22
-7.
4
-22
-7
5
-22
13
11. K=
9
1
51
-38
2
55
56
3
113 -
- 124
4
33
-45
5
-21
-16
6
-22
30
-9, K =
9
1
42
39
2
-20
20
3
92
-96
4
55
-5*
5
-21
2
6
-22
16
H =
-7. K-
9
0
1
-21
95
-7
-92
1
90
96
2
■ 98
97
2
-20
17
3
-22
14
3
-20
-0
4
4 4
-55
H-
10. K=
10
5
82
101
£
-21
4 2
0
-22
-35
7
-22
-5. K =
35
9
h-
1
2
-21
-22
12. K =
5
-6
1 0
1
52
-56
2
-20
1
0
-22
-21
~
3 1
-48
4
-21
-36
h-
12. K =
10
5
7 7
77
C
34
32
1
-22
22
7
-22
-26
2
67
-62
-3, K =
9
H=
10, K =
1 0
1
47
-46
1
-21
26
2
6?
-69
2
75
-03
3
56
-52
3
-21
-6
4
-20
-23
4
-22
-8
5
e3
52
b
4 9
50
F,=
-0 , K=
10
7
92 •
-100
H,=
H-
H=
H-
H =
r.-
1
-20
-4
2
-X9
-13
3
43
54
4
-20
12
A
ee
95
6
-21
41
7
40
-46
0. K =
10
0
32
41
1
2e
1 0
2
85
65
3
5 8
4a
4
-20
-1
5
-21
3
6
36
22
2, K=
10
0
147 -
-143
1
-20
-20
2
14 6
142
3
135
133
4
32
44
5
64
63
4, K=
10
0
132 -
■136
1
-20
6
2
-20
4
3
-20
-8
4
-21
-23
5
33
-19
6. K =
10
0
-20
24
1
122
•120
2
1 I 5
1 15
3
-22
6
4
73
-74
31
50
41
48
-22
H=
-6 ,
K=
-2 2
63
-28
59
-14
I 0
H=
H-
1
62
58
2
58
67
3
32
-29
4
1 12
1 1 I
5
-21
0
6
-22
-9
-4. K=
1 0
1
103
- 104
2
-20
"" J-
3
-20
16
4
■45
-50
5
-21
23
6
-22
-31
-2, K=
I 0
1
160
-157
2
71
-65
3
77
-72
4
4 0
-56
5
31
41
6
67
-64
0
31
1
-20
2
36
3
-21
4
■ 56
K= 1 1
9
1 5
- I'r
- 16
-54
K-
K=
0 -21
1 32
2 -21
3 -21
1 1
26
-0
14
4
H=
K= 10
188
H=
M =
1
1 (;
r C
L
FO
FC
L
1 a
FC
L
FO
rc
I.
2
4 5
-3e
H-
:
-0. K:=
1 1
4
4 7
oc
0
1
2
3
-?i
-21
-21
11
-27
-32
-13
-31>
1
-9. K^
37
-7, K-
1 1
-29
1 1
fr
1
2
3
4
-21
-21
-21
-3t K =
-Z7
-6 7
30
4
1 1
H-
1
2
3
4
-1. K=
-20
-21
-21
61
1 1
2
17
1 1
54
0
7. K-
79
1 1
-7 2
1
2
3
63
bl
-22
-1.2
-b2
-10
1
2
3
-21
3C)
31
61
3C
H
0
0. K=
107 -
12
106
1
Si's
40
Table B-4
jlated Stri.
(dhphpy) ]Cl^'2E^0
Observed and Calculated Structure Factors for [Ni,c€ (H„0) .-
2 2 4
190
L
FO
rc
L
FO
FC
l-
FO
FC
L
FO
F C
H-
6 . K •■
0
-4
41 ?.
-4 19
-21
194
-212
_
0 t K=
0
-2
60/
633
-27
-.93
-1 06
0
1 1 o J -
-1171
-26
284
-3^5
2
563
-4 9 0
2
3 015
2 9 ; i /
H=
12. K.=
0
-25
217
253
4
t 930 -
-20 to
4
91 1
905
-24
-93
- 193
f,
£.6 3
b'-JO
t>
Jt.3
-3'M
0
163 I -
- 1 722
-2S
^90
Mi2
{I
1 Mi
- 2 '.:. .1
0
9 0 5 -
- 1004
2
494
-506
-22
363
384
1 0
oev
-t.0 7
10
3 1 /
322
4
427
4 34
-21
-90
-60
12
314
-3. 'J
1^'
-79
6
6
-87
1 5?
-20
22 7
-375
14
-64
103
14
44 5
-4 34
8
-84
-76
- 19
328
- MjZ
16
130
-1«J
16
22 5
230
-28
b.>l
-54 1
- 10
-9 2
-25
1 0
1 4U
1 1 3
10
1 38
-9 3
-26
21 I
200
- 1 7
-90
-42 2
20
242
261
20
-04
-1 06
-24
194
107
-1 6
-90
4 \d
22
I 77
1 H4
-30
602
-57o
-22
142
-12o
-1 5
-96
-63
24
1 : &
-14?
-2 8
5r.0
5o7
-20
3 02
-399
- 14
-96
-292
26
700
-t)91
-2o
Yt 7
7 54
-1 8
l.-'7
-1/7
-13
5 53
595
-2 4
34 y
- J,:\,\
-1 d
3'. 7
35 7
-12
-JU
180
1=
2. K:
■ 0
-2?.
7o5
- / O 0
-1 '♦
249
2 56
- 1 1
490
- 522
-20
lo3
1 85
-12
181
- 180
-10
190
-24 7
0
403
3 7.1
-10
296
315
-10
-79
3d
-9
04 7
-8U7
2
2^30 •
-2014
-16
9 ^ 9
-921
-8
-79
61
-3
44 5
512
4
137
-1 i?4
-14
i t.7
197
-6
-80
- 14
-7
20 I
-2i2
6
345
-303
-12
167
1 19
-4
374
362
-6
79 8
-705
0
1 693
1 6 li 2
-1 0
14 7
-99
-2
1073
1 1 1 1
-5
14 10
1 4o2
JO
1 24
-119
-0
155 3
14 83
-4
02 7
-696
1 2
1 1 b
1 07
-6
;/73
9Jo
H =
14. K:
0
-3
39 3
2^*4
1 4
C4b
6 4 9
-4
01 6
7a 1
-2
85 7
72 8
16
505
-547
-2
2 4^6 ■
-2 5 05
0
50o
-594
-1
124
51
>8
2*j5
251
2
433
436
20
340
3 62
H =
9. K-
0
-24
-«3
-16
H =
3i K
= 1
22
342
-354
-22
346
-i^^
24
41 3
-402
0
39 5 7
41 00
-20
-8 1
66
0
750
-639
26
31 1
292
2
41 1
42 1
-1 8
284
27 7
1
34 8
31 7
■2 0
&'i9
-54 1
4
429
- 4 36
-I'i
30 o
-323
2
-70
- 126
-2 6
4*0
-459
6
d52
270 ■
- 14
171
-1 87
3
301
-331
-24
206
I i;i
0
-/o
-ai
-12
-3 1
-ill
4
390
-408
-22
4iJ6
443
10
-8 1
-123
-10
197
-2 2 6
5
559
559
-t:0
1 i i
-i09
12
i vo
- 1 9->
-6
141
136
6
-o7
1 9
-in
269
-274
14
-7 9
57
-6
394
J99
7
-67
-43
-16
060
046
lb
-8 I
-1 I
-4
371
360
8
472
-i»85
-14
560
-551
-30
4 /■2
474
-2
3 78
-41 1
9
447
- 40l
-12
283
-322
-20
5^:1
52o
10
-66
-92
- 10
^•73
3J2
-26
3'+l
-332
H =
1 6, K
r. 0
1 1
500
-51 o
-a
2573 •
-2519
-24
-78
18
12
-69
59
-6
13i!8
- lt>66
-22
- fa
-24
-16
322
-31 1
1 3
621
6C5
-4
329
-390
-20
-77
9i
-14
203
-207
14
199
233
-2
3358
3=05
- 18
1 39
1 60
-12
192
202
15
301
299
-15
448
-44o
-10
- 84
5
16
475
-478
i=
4. K
0
-14
31 5
-27o
1 7
3;jt>
-332
- 12
126
109
H =
1, K
1
18
-81
51
0
7 329
-84 96
- 10
zrt
-2 52
19
426
-4 55
2
242
-231
-8
130
100
0
1935
2098
20
41 1
39 8
4
1140
1 Kt?
-6
-Ci5
46
1
1 345
-1410
21
-ti2
-59
6
30f.
-2 3l>
-4
1 2 J 9
-123 7
2
1 054
-1916
22
450
-430
a
351
-306
-2
lo-v3
-lL.68
3
617
-5 6^
23
273
24 3
10
9^
120
4
1209
- 1 loa
24
-84
44
12
4 25
433
H-
10, K.
0-
5
712
-736
-29
-103
- 181
14
199
-2^7
6
347
^^J
-26
-1 00
-2iA
16
-«0
86
0
655
660
7
^.\<i
-273
-27
264
291
1 8
-80
27
2
942
-965
8
1 87
-142
-26
1 38
-171
20
271
-205
4
4^4
-AM
9
172
193
-25
200
24 9
22
195
-158
6
-80
9o
10
256
-24 1
-24
5o9
577
-JO
4 69
-4.54
d
5^9
52 7
1 1
700
-o93
-23
40o
-433
-2d
396
-3H9
10
d:il
-2to6
12
I 185
1242
-22
316
327
-26
574
373
12
I '♦O
-I •->3
13
-70
46
-21
Zii
-24 0
-24
21 »
2 09
- JO
51 4
502
14
438
4 j/
-20
683
-670
-22
216
-2 17
-28
226
-dZJ
15
793
7 -J 7
-19
-74
-I 04
-20
42 7
-41 7
-26
0J9
-032
16
-7o
1 45
- 18
i71
573
-IB
192
I o2
-24
1 I 3
129
17
310
3 15
- 17
39 2
392
- 1 t>
67 4
65 7
-2ci
06 8
o75
18
353
-3e.4
- 16
352
362
-14
134
126
-20
I Jl
-1 0-.
19
-82
-57
- 15
1384
I 34 5
- 12
31 0
2 4 0
- 18
o<\ i.
-ol 9
20
551
565
- 1 4
C4 3
-681
-lO
565
04 2
-1(>
7 59
7bd
2 1
25 1
-2 J3
- 1 3
105
- 1 08
-O
669
5'Jd
-14
6'>i
349
22
-82
-4 T
-12
16 7 4
-1 624
-6
219
-I 4 r
-l^
-7 d
5 7
23
336
-356
- I 1
I 773
-I 789
-4
427
3^10
- 10
319
325
24
670
-65t>
-10
723
640
-2
1524
1519
-d
574
- 5 •-' 0
25
-91
1 84
-9
-6?
80
-6
519
- 544
2o
-8 5
-23
-8
148
- 1 '» i
191
FO
FC
FU
FC
FO
FC
FU
FC
-7
2'.il
230
12
1 1 7
38
-9
73 5
-721
-1 1
-81
-21
-6
7'j3
-76 5
13
1 23
-1 55
-0
144
157
-I 0
-"80
32
-5
607
-574
1 4
I 75
-151
-7
51 7
-5 0't
-9
201
245
-4
1 O'^A
lOJL,
1 5
-80
-87
-6
206
-191
-3
-u2
- 108
-3
A t>9
-4 83
1 t>
1 4 9
153
-5
428
431
-7
29->
332
-2
1 73 7
1655
1 7
-U4
150
-4
3 05
-38 5
-6
-80
- 10
-1
J 00£.
-945
13
126
70
-3
203
210
-5
2 57
-24 0
19
2a J
2 54
-2
448
-455
-4
319
32 2
1^
&. K =
1
-30
-84
3 3
— 1
-73
- 39
-3
2 25
-218
-29
200
^^.i
-2
357
3oy
0
lii66 -
-1596
-23
48o
47 3
H-
11, K-
1
-1
-84
1 7
1
942
945
-27
Jl 2
-317
2
9b 'i
923
-26
2 95
2o.j
0
-3 2
34
H =
15. K
1
3
405
4 39
-2 5
338
- J 3 -:>
1
-8 2
5 8
4
J'l lb
14 42
-24
47 /
- 4 o 4
2
391
-3 78
-22
1 53
-118
5
3l>0
372
-23
393
407
3
- 00
-44
-21
12o
182
6
3'iO
-34/
-22
314
-331
4
-8 1
-4
-20
277
2 73.
7
3v0
-379
-21
2<*6
208
5
271
270
- 19
-8y
5o
O
330
-338
-20
43 1
t7y
6
221
2?6
-18
-84
55
9
356
-360
- 19
-7 :i
22
7
-82
77
-1 7
-34
9
10
570
553
- 18
450
-4 55
C
234
-19 9
-16
297
-2 77
11
615
64 0
-17
-70
-15
9
171
-13/
- 15
41b
-4 15
12
452
-4 50
-It.
337
-32 8
10
236
-214
- 14
-85
- 1 1 3
13
176
21 S
-15
032
-c :-:'.!
1 1
228
-237
- 1 3
20 8
-2 19
l'»
365
-342
-14
21 2
2 09
-29
24 2
-2 4 0
- I 2
300
3 02
lb
^65
-462
- 13
25/2
-2 7 8
-28
320
-30 7
- 1 1
416
4 1 4
1&
23C
-205
-1 2
1 02 9
I Ct3
-27
206
215
-1 0
-o5
-85
17
204
-229
- I i
1070
1 Ojb
-2o
357
-349
-9
188
1 74
18
-81
1 ^4
- 10
39 5
-403
-25
307
3 0 0
-0
-85
-31
19
-81
-1 1
-9
-70
7 0
-24
300
306
-7
1 81
-173
20
276
-275
-0
-70
1 7
-23
297
-29 5
-6
2 52
2 ;. 8
21
-64
79
-7
4 8 5
-480
-22
298
28 3
-5
157
-123
22
-84
3
-5
99/
9o3
-21
316
-502
-4
-86
- 14
•30
561
-545
—5
-70
-3l.
-20
632
-630
-3
-87
47
■2 9
24 5
240
-■i
886
- 8 ct 0
-1 9
165
-14 3
■20
-61
-14
-3
5 7 4
5 •■-17
-1 8
I 1 7
120
H =
0. K.
= 2
■27
-82
152
-2
2150-
-2161
-1 7
-80
09
2<.
42 1
4 15
-1
1041
1 0 25
-16
524
541
0
321
-349
25
219
-236
-15
7 53
770
1
90
250
•24
319
2 93
H =
9, K:
1
- 14
-78
13
2
76 i
-703
23
582
-56 8
-13
249
275
3
23B
-327
■22
687
-601
0
700
712
-12
579
-554
4
402
4^5
21
-77
4
1
348
-34 7
-i 1
59f
-6 0 1
5
614
-•+90
•20
3;; 3
369
2
18 /
-1 :;.,:
-10
143
151
o
M3
t.7
•19
5'j1
583
3
-7 7
-53
-9
-77
-105
7
8 76
02 1
•18
519
4 OfJ
4
443
-447
-8
-76
-2 3
8
550
53 7
•17
69 0
69 4
b
21 3
-2^ o
-7
128
at
9
6 5C
662
-16
50b
-4^77
6
-dO
-27
-6
29 7
-267
10
3 7t
-3 76
■1 5
1 2 3
55
7
-80
43
-5
-78
-33
1 1
-71
-3
•14
-64
55
a
1 1 9
63
- 4
290
2 92
12
7 1 5
-74 2
13
702
-622
9
1 29
1 50
-3
14 1
-14 4
1 3
I 073
-1 095
■12
566
-5t.O
10
27 ^
-2 86
-2
695
904
1 4
975
981
■1 1
328
2 85
1 1
243
-Zod
- 1
40/
-4:^7
1 5
-73
-38
•10
443
39J
12
-B 1
41
1 6
*09
426
-9
1 40
1 4 8
13
22 1
-199
H=
13, <
1
I 7
-86
-31
-8
425
408
14
1 62
1 46
18
4J2
-457
-7
319
275
15
2z.o
2 3 2"
0
61 1
-o'H
19
-9 4
-80
-6
34 b
29 7
-30
4 97
'19 1
1
228
25-'
2 0
264
-311
-5
476
-4 4 9
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-1 b
21 1
-2 0 9
6
147
-I 1 9
-8
2 74
-£87
-1 5
-84
-86
7
leo
- 1 65
-7
2.<0
229
rl=
0. K=
14
- 14
16 6
205
8
2f-0
-24 2
-6
170
-171
-13
-dJ
86
9
-85
-114
-5
-86
2 8
0
746
-779
-12
1 28
-73
10
-84
55
-4
390
3 c' 6
1
-ti J
-50
- 1 1
210
220
I 1
245
221
-3
328
- 334
2
-80
-4 1
-10
142
60
-1 3
4'! 0
-4 4 5
3
50 2
-479
-9
1 48
-1 60
-12
130
-4 7
H =
0. K =
16
4
-fiO
62
-8
270
281
- 1 1
3 76
377
5
3i 3
315
-7
261
270
-10
-82
- 6
0
237
-274
6
41 1
4 09
-6
31 4
- J4 6
-9
265
27 9
1
-85
-93
7
407
399
-5
208
24 0
-8
1 9 1
153
2
153
I 1 3
e
1 1 7
-125
-4
-81
-47
-7
1 99
-158
3
14 0
■)1
9
231
-271
-3
3d8
-o20
-6
433
4 36
4
-84
79
10
-81
-54
-2
-81
-116
-5
402
-438
5
273
253
1 1
-62
65
-1
-79
-16
-4
-as
93
6
-84
-33
12
1 4b
120
-3
300
294
7
1 -^^
- 1 53
13
157
I 12
H =
6 . K-
= 1^
-2
37 1
-402
8
1 32
1 <+6
14
1 91
-200
-1
-82
1 5
1 &
-04
46
0
339
o32
H =
2, K=
1 0
1
.if a
233
H =
3. 1^:
15
H-
2, K.=
14
2
36 1
-378
0
-85
4b
3
-8 3
- 6
0
302
310
1
-84
-77
0
128
-140
4
283
-271
1
-63
-38
2
-8 5
123
1
123
-1 64
5
3o5
-3 55
2
360
346
3
-85
1 33
2
465
463
6
-86
60
3
208
2 88
4
185
132
3
-81
4 1
- lo
1 20
1 1 4
4
-85
36
o
-86
-72
4
277
252
- 1 5
-86
-67
5
24 9
-257
-9
3'.ji
354
5
344
358
- 14
-84
92
6
326
-307
-8
I 57
1 55
6
-60
-32
-13
234
225
7
127
-1 00
-7
404
-4 1 0
7
355
-335
-12
164
-1 79
8
260
-185
-6
2 85
-242
8
132
-1 1 0
- 1 I
-32
-41
-13
207
202
-5
1 74
- 191
9
161
-134
-10
-84
51
-12
196
1 49
-4
24 1
-a J 5
10
199
182
-9
-33
34
- I 1
427
398
-3
1 67
1 ■>6
1 1
-85
25
-8
lo8
- U,3
- 10
-8 5
30
-2
1 4o
- 1 25
12
-87
-144
-7
447
4 1 8"
-9
-82
-18
-1
-85
1 7
1 3
238
-205
-6
1 31
-15 1
-8
298
310
-I 6
194
-IB2
— 3
300
-324
-7
2 29
-21 0
H =
4 , K
= 1 6
— 1 5
-az
4
-4
-81
58
-6
-84
57
-1 A
-04
-64
-3
320
-294
-5
-85
-23
0
264
249
-13
2C4
-182
-2
422
4 42
-4
53/
-52 5
1
-86
I 0 9
-12
170
220
-I
-3J
50
-3
34 6
34 7
-7
253
- i;4 9
-1 I
-8 1
106
-2
173
-120
-6
-85
-d3
-10
-&1
-122
H =
8. K
14
-1
33)
-32 1
-6
2 10
2 1 7
-9
-80
-1 04
-4
-86
- I 0 3
. -8
2?4
201
0
382
-377
H =
5, K
15
-3
129
I 34
-7
402
-451
-13
-8 4
-53
-2
140
- 1 22
Table B-5
Observed and Calculated Structure Factors for C^ (fph) ^Rh (cp) (tpp)
205
FO
FC
H=
K =
1
Jr
3
4
5
6
7
8
9
10
1 1
12
13
14
15
16
17
-21
1C97
67 1
21 3
<tCB
334
12A7
t.31
7iy
361
-bO
3^2
!<4
&3S
214
32 5
138
1 OP
■1630
-f*?2
_ I o ^
- 21 1
-1 240
73 3
344
39
-7.<>o
-172
53 6
234
— ^ <* "^
-173
K-
0
1
2
3
4
5
6
7
6
9
IC
1 1
12
13
14
15
16
-18
-17
-16
-15
-14
-13
-12
- 1 1
-10
-9
-8
-7
-6
-5
-4
-3
-2
-I
164 4
155
30 1
1 179
332
I 2a9
128
53 7
3&9
254
41 0
-63
427
120
2S2
— ^, *!
22 5
-C7
153
192
-6 9
3:) 3
-53
432
123
t20
331
257
63 1
308
S"J9
IC2
50d
1102
552
1
-2456
-Bl
-- 1 5 4
1 cr4
-259
- 1 r63
-loe
51 9
423
-?48
-423
-6
403
134
-2G3
1
237
-9
17 4
107
-90
-375
-52
4 ■'5
134
-84 2
-304
250
CO 7
235
-91 5
-36
553
I 44 9
-G50
K =
0
1
2
4
5
6
7
8
9
10
1 1
1?
13
14
15
-19
797
4 4't
61 1
12«t3
157
114 7
7 7
3-^8
3e.a
24 3
329
-66
323
-6/
301
-70
104
195
-363
-772
-1260
223
1 1C7
14
-37 5
-344
252
3 34
-30
-317
3 6
30 1
38
86
■18
■17
-IC
■15
■I 4
-1 3
-12
-! 1
-10
-9
-r>
-7
-6
-5
-4
-3
-2
- 1
FO
177
-65
190
187
172
-61
617
5^ 1
4 60
313
52 2
1415
-b^
1607
353
-45
920
1C6
FC
173
22
-191
183
157
-6 0
-62 1
-50 4
453
299
-537
■14 9 3
-53
1629
42V
18'-'
-518
154
K=
0
1
2
3
4
5
6
7
8
9
10
1 1
1 2
13
14
-19
-18
-17
-1 6
- 15
-14
-13
-1?
-11
-10
-9
-8
-7
-C
-5
-4
-3
-2
-1
1 047
30 7
559
46 4
1 ' 9
27-
-55
2t7
-62
21 I
33 0
-69
2 93
-69
130
2 4 4
3). 1
35 7
-66
23 V
1 53
1 16
l'*0
3 c?.
-54
196
2 20
369
163
964
254
9-i9
1 16
I 1 45
H=
0
1
2
3
4
5
6
7
0
9
10
II
12
13
■20
-19
-18
-17
-16
-15
-57
286
59 1
624
62b
122
456
14 1
-t>t>
165
26 0
358
104
150
390
-66
414
-64
-OJ
- 14
-13
-12
- 1 1
- 10
-9
-6
-7
-6
-5
-4
— 3
-2
-1
FO
223
374
410
4S6
176
409
21 7
238
160
1 1 C2
838
550
682
-57
1".=
699
■26 0
525
442
1 86
2 18
279
104
• !97
-338
85
29 6
-o4
- 128
-243
-3i<1
363
9 4
-232
- 146
-89
145
406
-1 54
-201
201
32 2
-210
- I 035
-223
-776
253
-997
-64
307
-6 1 0
-6 19
3 28
6 0-O
-103
-4 8 8
-112
6 0
153
- 26 1
-35?
-125
— 138
384
2
-407
-18
71
0
1
2
6
e
ic
:i
12
-20
-19
-16
- 17
-16
- 15
- 14
-13
-12
- 1 i
- 10
-9
-8
-7
— 6
- 5
-4
-3
— 2
- 1
FC
336
348
-4 02
- 5 1 5
180
431
2C6
-262
-226
1 C6 8
897
-5C9
-613
25
K-
2 53
337
6 48
993
301
46C
167
235
165
543
305
135
238
il >
- iS
423
218
184
222
1 0 8
862
720
<;4
4 87
341
470
41 7
efc2
1307
1 195
130
4 1 8
0
I
2
-^
4
5
6
7
8
9
10
1 1
20
• 19
■ 18
■ 17
■ 16
- 1 5
- 14
- 13
- 1 2
- 1 1
-I 0
-9
-8
1 16
3£5
IBB
2 15
1 69
355
I'lS
213
192
132
-7 1
-72
-67
177
139
163
£27
-11 5
279
1 3S
330
693
?9'-.
ZC9
34 7
-371
646
9 86
-269
-475
165
223
151
- 15t-
'305
1 6 -V
252
5t>
-307
-52
428
237
J75
-228
96
852
74 1
122
- 4 7 7
-323
- 4 6 '1
J4l
-722
- 13C6
1 156
165
4 75
1108
379
-178
-2iO
U>9
357
129
-212
-205
147
98
-S8
-66
177
147
-191
-C3e
-124
283
- l^fa
-344
-63 0
61
SG9
21 1
-7
-6
-5
-4
-3
-2
- 1
FO
4 61
526
-56
'- 56
567
90
470
0
1
2
3
4
5
e
7
8
9
-2 1
-20
-19
-18
-17
-16
-15
-14
-13
-12
-1 I
-10
-9
-8
-7
-6
— 5
-4
-3
-2
-1
H-
0
1
2
4
5
6
7
8
-2 1
-20
-19
- 18
-17
-16
-15
-14
-1 3
-12
-1 I
- 1 C
-9
— 8
-7
-6
-5
-4
-1
h=
590
105
6 0 6
-66
-67
252
173
244
1 13
205
242
-67
93
-64
-i>5
4 52
217
395
1 8 0
300
44 1
145
^38
370
176
1 02
330
-54
134
326
275
FC
-489
-544
4 5
-6
-56 0
6
-415
-603
-107
4 1 5
-6
1
-24 1
- lol
249
132
-U'8
23 7
81
-86
-7 1
-4 1
4-')9
216
-389
-188
309
415
-14 9
-453
-381
199
41
-33 7
-20
1 28
367
292
K-
230
242
-67
-7 0
1^;0
262
-70
21 4
108
326
-68
-&7
173
-68
4Cl
-65
/»m5
24 7
148
425
194
464
1 16
541
300
573
390
-60
799
145
235
- 24 1
57
-94
-1 18
2c9
73
-24 5
-72
-325
-1G3
60
16/
146
-380
-7
455
■^32
-176
-4 14
206
474
-83
-546
-295
55 7
39 2
-22
-323
-142
K=
444
— 4 4 9
206
I o
PC
FO
fC
ro
FC
I o
FC
1
?
3
4
b
6
-?C
- jy
-It)
-17
-16
-lb
-14
300
-39 3
-2
-07
17
-10
521
499
-1 4
129
1 1 1
310
3i; J
30?
3! 1
-1
-67
-80
-14
-13
2h7
300
29/
-2^7
- 1 3
-12
-5tt
'80 8
- > 3
-781
— ty H
1 ?
n-
0 • K =
12
-12
2 36
-24 4
- 1 1
4i:3
-44 5
112
— '/ 0
-40
0
1 I 7
1 08
- 1 I
- 10
3.'" 4
IV 8
-3 03
172
- 10
-9
463
962
51 I
9 09
100
-66
: 03
-66
<i'^4
Ibl
b?. 2
1 15
79
-?6C
6 3
449
- 170
-534
-to
-IM
- 17
- Id
-J b
-J4
- 1 3
260
260
2-.4
-6 7
177
ZJ3
260
2/0
-36
-233
-C.3
174
i:b2
-9
-8
-7
-6
- 5
-<
-3
-5?
eo3
7:'i
1 C C 3
704
31 4
&J
-7bO
-boV
732
914
- V 1 7
-59 3
-8
-7
-6
-5
-4
-J
-2
404
A30
5:'5
1231
403
134 7 -
1406 -
-43H
-4 13
-4 33
12. 3
3o7
- 161 H
-1657
3i 7
-13
-63
1 1
-12
106
-220
-2
(.d2
-950
- 1
-51
-1?
-62
25
-1 1
345
-351
- 1
1 174
241 6
1 . K;
3
-1 1
-02
?7
-10
1 00
-.9
ti-
-10
-<i
-8
-7
-6
-5
-A
— 3
166
-O 1
-If',''
-r5o
-?4
-o
-r,
-7
263
130
2'iJ
2V0
17?
-205
0
1 , K-
t\ 4
= 1
-454
0
1
904
308
-&7I>
303
2Ha
20 3
27 I
1^0
207
3oe
??i
-26 b
-?3C
-277
-6
-5
-4
-3
-2
109
-fcV
129
2 1 U
145
-150
64
159
-22 9
-1 39
I
2
->
4
5
139
7 99
J en
3t.7
ero
-216
929
134
-355
-755
2
3
4
5
6
771
4 03
I 19
50ii
98
757
421
107
-471-
-86
_2
529
52 7
-I
-71
-48
6
f:o4
85o
7
315
339
-1
-oB
-6 b
K=
0 . K-
: 13
7
8
7ti0
2/2
788
-293
8
9
-64
313
-12
-305
K=
Oi K-
= 10
9
50 I
-492
10
276
-2t,&
-17
1 25
103
10
21 0
-214
I 1
22:i
196
0
43 0
4 26
- 16
132
134
1 1
153
132
12
320
31 /
1
2
11 0
-68
144
-99
-15
-14
1 00
147
92
- 138
1?
13
4 03
-6L>
401
-30
I 3
14
180
245
- I /t>
-236
3
4
112
-71
-125
-4 9
-1 3
-12
225
-oe>
-231
34
1 4
15
r t9
-25fc
-63
-2 0
-19
-09
3 54
06
-346
— ?0
1 7 <■■
- 1 73
-1 1
-70
122
IC
147
130
-18
-60
-45
-ly
-IK
-17
-0 7
20 0
360
76
206
-37 /
-JO
-9
~C
-6/
-o9
10>j
67
-56
- 107
-19
- lo
- 17
-67
-CO
192
-30
23
217
- 1 7
- 16
- to
329
132
120
328
:c6
130
- 16
-lb
- 1 'i
488
24 1
575
-40 3
25 1
566
-7
-6
-5
-t.9
107
1 66
5 1
136
-1 4o
-16
-15
- 14
3J. <.
1 61
3 JO
308
-174
-3C7
-14
- I 3
- 12
324
247
696
-325
-230
fat!3
-13
3»J7
397
-4
-73
- ir.8
- 13
103
109
- 1 1
595
5fc>7
- \2
-1 1
-10
-<»
— 6
174
228
34 3
603
-66
-196
-23 3
34 5
eoi
82
-3
H=
-15
106
0 t K^
137
120
14
-12?
-12
-1 1
- 10
-9
-8
37 3
120
- 5 1
3^5
1 15
373
147
-23
-370
190
-10
-9
-8
- 7
-6
-51
471
1 11
297
191
— 90
-481
107
362
206
-7
376
-37C
-14
1 60
1 1? 6
-7
4 2 4
41 9
— 5
269
-242
-6
-68
-136
-13
20t>
2 06
-6
f.C4
-5bo
-4
1 099
-1125
— 5
107
94
-I?
-72
-149
-5
700
-731
-3
1222
1037
-4
42 1
400
-1 1
21o
-219
-4
407
-471
-2
lirie?.
116 4
-3
-70
1 10
-10
-70
47
-3
73
-4 14
- 1
715
V4 1
-2
AbS
-401
-9
171
165
-2
6C0
237
-1
-7 J
-75
•■f^
-7
148
-72
133
-74
- 1
e76
102
H--
1 t r
= 4
H=
0, K
= 1 1
H=
It K
= J3
H =
1. K
2
0
1
340
215
297
205
0
1
-70
1 fO
-3f
- 1 49
0
833
67 1
0
1
1 i3b
15b
1536
ICO
2
3
690
-040
-347
2
-7 J
72
I
13b5
- U OU
2
O09
-546
4
636
608
-20
1 79
16 0
2
070
-4 4 1
3
2C:i
-342
5
34 1
3 '4 9
- 19
2'i'i
-254
3
2 64
-36 9
4
775
fcC4
6
1 78
177
- 1 C
I 7m
- 1 90
4
71C
-636
C
2 14
26 9
7
I 17
103
- 17
lb'.
156
5
927
699
6
34 1
-343
0
1 44
- 1 09
- 16
HiO
-1 72
6
IC64
- I r 2 1
7
4 53
-48J
9
291
3J 7
- 15
It. 6
165
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-6 7
-6C
99
-119
-7
107
-68
103
88
- 12
255
-249
131
-2
- 1
22 2
-66
-204
53
-6
-5
2C3
346
- 2 0 5
-371
-1 1
-10
-67
14 1
42
120
H=
11. K =
-2
H==
12. K-
0
-4
-3
-07
305
65
309
-9
-8
133
-67
150
-.■14
0
1
-15
- l<
-13
-12
160
-t>9
-174
-6 6
-1 1
1 14
1 14
-2
-1
J F.O
197
145
-216
-7
-6
222
1 10
-24 9
84
-66
233
-67
20b
-40
-246
-??
303
-10
-9
-0
20 7
230
10 1
-213
-203
102
H =
-1 1
12. K-
-67
- -5
-38
-5
-4
-3
-2
223
-67
123
167
225
23
- 1 5 1
-148
-1 1
-10
-9
-e
-7
-fc
-5
-«
-3
-2
-1
-66
2b9
-9
--3 2
- 2r 4
0
12c K=
172
■ -8
- 199
-IC
-9
-e
211
-66
142
21 b
15
- 137
H=
12. K=
-2
-c'3
27 1
- t,7
Ci02
-66
199
-60
-6,.
-78
274
-5 1",
-6
-5
-4
-6H
149
1 20
-25
-150
-138
-7
-6
-5
106
1 4?
293
-66
J20
2i.7
-12
-1 1
-10
-70
-60
1 14
132
60
-02
-«og
-6?
194
35
7
-3
-2
-1
-66
160
1V4
12. K:
93
143
-161
-- -7
-4
-3
-2
-1
H =
-69
208
1 17
217
12. K=
60
-233
-157
229
-4
-9
-a
-7
-6
-5
-4
183
103
27 0
120
210
1 10
-201
1 16
302
-81
-219
-101
H=
1 ! . K:
= -I
0
-6
146
155
122
- 143
-1 1
-69
-25
H=
12 , K^
-1
0
-1&
-14
-13
-12
-11
— 10
35b
162
377
-70
2S7
-66
-60
352
136
37 5
-115
-2nfj
-68
94
-7
-6
-5
-4
-3
-2
-1
130
-69
26 4
119
210
132
177
-134
60
27 9
101
-236
- 11 9
191
-10
-9
-8
-7
-6
-4
226
-66
-65
150
-67
153
103
-235
-75
26
176
42
-158
-6b
- 12
-I 1
-10
-5
-8
-7
165
97
193
201
127
213
-152
-103
185
220
- 129
-214
-9
25 e
301
-3
177
147
-6
-67
4C>
— C
-6A
-1 4
H =
12, K:
-6
-2
1 1 1
14 1
-7
30 1
- 2Ut
. -1
IbO
- 1^4
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BIOGRAPHICAL SKETCH
Douglas Allen Sullivan was born November 9, 1945, in
Huntington, West Virginia. In May, 1963, he was graduated
from Vinson High School, Huntington, West Virginia. He
received the. degree of Bachelor of Science in Chemistry from
Marshall University in May, 1967. After studying at the
University of Florida from September, 1967, to August, 1968,
Mr. Sullivan taught chemistry, physics, physical science,
and mathematics for the Wayne County (West Virginia) Board
of Education. He then returned to the University of Florida
in September, 1972, and received a Master of Science in
Teaching degree majoring in chemistry in December, 1974. He
is a men\ber of the American Chemical Society. Mr. Sullivan
is married to the former Jeanie Delaine Puckett of Titusville,
Florida. They have a three-year-old son, David 0' Donald
Sullivan.
237
I certify that I have read this study and that in my
opinion it conforms to acceptable standards of scholarly
presentation and is fully adequate, in scope and quality,
as a dissertation for the degree of Doctor of Philosophy.
Gus J. Palenik, Chairman
Professor of Chemistry
I certify that I have read this study and that in my
opinion it conforms to acceptable standards of scholarly
presentation and is fully adequate, in scope and quality,
as a dissertation for the degree of Doctor of Philosophy.
'^^^C^/i-L^
R. Carl Stoufer
Associate Professor d\
Chemistry
I certify that I have read this study and that in my
opinion it conforms to acceptable standards of scholarly
presentation and is fully adequate, in scope and quality,
as a dissertation for the degree of Doctor of Philosophy.
George E. ^yschkewitsch
Professor of Chemistry
I certify that I have read this study and that in my
opinion it conforms to acceptable standards of scholarly
presentation and is fully adequate, in scope and quality,
as a dissertation for the degree of Doctor of Philosophy.
John F. Helling (^
Associate Professor of
Chemistry
I certify that I have read this study and that in my
opinion it conforms to acceptable standards of scholarly
presentation and is fully adequate, in scope and quality,
as a dissertation for the degree of Doctor of Philosophy.
Richard R. Renner
Professor of Education
This dissertation was submitted to the Graduate Faculty of
the Department of Chemistry in the College of Arts and
Sciences and to the Graduate Council, and was was accepted
as partial fulfillment of the requirements for the degree
of Doctor of Philosophy.
December, 197 5
Dean, Graduate School
.'ii i^-^"^^'^'^
KU2 7.6. 45.79