metal-organic compounds
The crystal structure of the title compound, [Ni(C15H10Cl2N2O2)(C5H5N)3]·C5H5N, is built of molecules of a mononuclear nickel complex and uncoordinated solvent pyridine molecules. The NiII atom in the complex is coordinated by two O and one N atoms of the meridional tridentate ligand, viz. the twice deprotonated hydrazone formed from 2-hydroxy-5-chloroacetophenone and p-chlorobenzhydrazide. The remaining three coordination sites of the Ni octahedron are occupied by three coordinated pyridine ligands.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804020756/ya6210sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804020756/ya6210Isup2.hkl |
CCDC reference: 251627
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
{4-Chloro-2'-[1-(5-chloro-2-oxidophenyl)ethylidene-
κ3O,N2',O']benzhydrazido}tris(pyridine-κN)nickel(II) pyridine solvate top
Crystal data top
[Ni(C15H10Cl2N2O2)(C5H5N)3]·C5H5N | F(000) = 1440 |
Mr = 696.26 | Dx = 1.393 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.6009 (17) Å | Cell parameters from 3704 reflections |
b = 20.845 (3) Å | θ = 1.8–27.0° |
c = 12.6417 (17) Å | µ = 0.79 mm−1 |
β = 90.418 (3)° | T = 273 K |
V = 3320.4 (8) Å3 | Block, yellow |
Z = 4 | 0.27 × 0.20 × 0.12 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 7232 independent reflections |
Radiation source: fine-focus sealed tube | 4961 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.0°, θmin = 1.8° |
ω scans | h = −16→14 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −26→17 |
Tmin = 0.816, Tmax = 0.912 | l = −16→14 |
19309 measured reflections |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.141 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0618P)2 + 0.4914P] where P = (Fo2 + 2Fc2)/3 |
7232 reflections | (Δ/σ)max < 0.001 |
415 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.68463 (3) | 0.251764 (18) | 0.79921 (3) | 0.04659 (14) | |
Cl1 | 0.90879 (9) | 0.57717 (5) | 1.15759 (9) | 0.0972 (4) | |
Cl2 | 0.64239 (9) | −0.06396 (5) | 1.04394 (8) | 0.0888 (3) | |
O1 | 0.72473 (15) | 0.34046 (9) | 0.85308 (15) | 0.0510 (5) | |
O2 | 0.65929 (16) | 0.16031 (10) | 0.76798 (15) | 0.0546 (5) | |
N1 | 0.77760 (18) | 0.28160 (12) | 0.99974 (18) | 0.0477 (6) | |
N2 | 0.73832 (17) | 0.22878 (12) | 0.94439 (17) | 0.0448 (5) | |
N3 | 0.62892 (19) | 0.28098 (13) | 0.65054 (19) | 0.0544 (6) | |
N4 | 0.8431 (2) | 0.24622 (13) | 0.73121 (19) | 0.0531 (6) | |
N5 | 0.52251 (19) | 0.26679 (13) | 0.85132 (19) | 0.0543 (6) | |
N6 | 1.0462 (7) | 0.0096 (3) | 0.8498 (4) | 0.157 (2) | |
C1 | 0.8385 (3) | 0.39400 (17) | 1.1026 (3) | 0.0658 (9) | |
H1B | 0.8395 | 0.3557 | 1.1405 | 0.079* | |
C2 | 0.8716 (3) | 0.45039 (19) | 1.1513 (3) | 0.0737 (10) | |
H2A | 0.8946 | 0.4500 | 1.2214 | 0.088* | |
C3 | 0.8702 (3) | 0.50610 (17) | 1.0958 (3) | 0.0649 (9) | |
C4 | 0.8380 (3) | 0.50762 (16) | 0.9928 (3) | 0.0690 (9) | |
H4A | 0.8378 | 0.5459 | 0.9551 | 0.083* | |
C5 | 0.8057 (3) | 0.45108 (16) | 0.9454 (2) | 0.0621 (8) | |
H5A | 0.7843 | 0.4518 | 0.8749 | 0.075* | |
C6 | 0.8042 (2) | 0.39420 (14) | 0.9989 (2) | 0.0476 (7) | |
C7 | 0.7658 (2) | 0.33472 (14) | 0.9457 (2) | 0.0442 (7) | |
C8 | 0.7433 (2) | 0.17353 (15) | 0.9918 (2) | 0.0473 (7) | |
C9 | 0.7939 (3) | 0.16763 (16) | 1.0998 (2) | 0.0651 (9) | |
H9A | 0.8191 | 0.2089 | 1.1224 | 0.098* | |
H9B | 0.8523 | 0.1382 | 1.0966 | 0.098* | |
H9C | 0.7424 | 0.1521 | 1.1492 | 0.098* | |
C10 | 0.6987 (2) | 0.11600 (14) | 0.9410 (2) | 0.0477 (7) | |
C11 | 0.6608 (2) | 0.11300 (15) | 0.8344 (2) | 0.0495 (7) | |
C12 | 0.6219 (2) | 0.05356 (16) | 0.7987 (3) | 0.0604 (8) | |
H12A | 0.5985 | 0.0505 | 0.7290 | 0.073* | |
C13 | 0.6165 (3) | 0.00004 (16) | 0.8606 (3) | 0.0670 (9) | |
H13A | 0.5898 | −0.0382 | 0.8334 | 0.080* | |
C14 | 0.6511 (3) | 0.00366 (15) | 0.9635 (3) | 0.0589 (8) | |
C15 | 0.6915 (2) | 0.05968 (15) | 1.0025 (3) | 0.0570 (8) | |
H15A | 0.7153 | 0.0608 | 1.0723 | 0.068* | |
C16 | 0.6387 (3) | 0.34126 (19) | 0.6187 (3) | 0.0753 (10) | |
H16A | 0.6732 | 0.3702 | 0.6631 | 0.090* | |
C17 | 0.6005 (4) | 0.3629 (2) | 0.5235 (3) | 0.0966 (14) | |
H17A | 0.6088 | 0.4055 | 0.5034 | 0.116* | |
C18 | 0.5497 (3) | 0.3202 (3) | 0.4589 (3) | 0.0963 (15) | |
H18A | 0.5226 | 0.3335 | 0.3939 | 0.116* | |
C19 | 0.5390 (3) | 0.2579 (2) | 0.4900 (3) | 0.0818 (12) | |
H19A | 0.5046 | 0.2282 | 0.4469 | 0.098* | |
C20 | 0.5800 (3) | 0.24026 (19) | 0.5862 (3) | 0.0674 (9) | |
H20A | 0.5732 | 0.1977 | 0.6073 | 0.081* | |
C21 | 0.8990 (3) | 0.29798 (18) | 0.7087 (3) | 0.0763 (11) | |
H21A | 0.8704 | 0.3379 | 0.7249 | 0.092* | |
C22 | 0.9970 (3) | 0.2960 (2) | 0.6627 (3) | 0.0929 (13) | |
H22A | 1.0326 | 0.3338 | 0.6463 | 0.111* | |
C23 | 1.0414 (3) | 0.2384 (2) | 0.6414 (3) | 0.0829 (12) | |
H23A | 1.1087 | 0.2355 | 0.6121 | 0.099* | |
C24 | 0.9843 (3) | 0.1851 (2) | 0.6643 (3) | 0.0894 (12) | |
H24A | 1.0118 | 0.1446 | 0.6498 | 0.107* | |
C25 | 0.8862 (3) | 0.19094 (18) | 0.7088 (3) | 0.0709 (10) | |
H25A | 0.8483 | 0.1538 | 0.7237 | 0.085* | |
C26 | 0.4538 (3) | 0.2199 (2) | 0.8600 (4) | 0.0881 (13) | |
H26A | 0.4773 | 0.1780 | 0.8497 | 0.106* | |
C27 | 0.3487 (3) | 0.2297 (2) | 0.8837 (4) | 0.1131 (18) | |
H27A | 0.3024 | 0.1950 | 0.8878 | 0.136* | |
C28 | 0.3131 (3) | 0.2890 (2) | 0.9009 (4) | 0.0965 (14) | |
H28A | 0.2425 | 0.2963 | 0.9181 | 0.116* | |
C29 | 0.3826 (3) | 0.3385 (2) | 0.8925 (4) | 0.1029 (15) | |
H29A | 0.3608 | 0.3805 | 0.9037 | 0.123* | |
C30 | 0.4854 (3) | 0.32479 (19) | 0.8673 (3) | 0.0798 (11) | |
H30A | 0.5324 | 0.3590 | 0.8610 | 0.096* | |
C31 | 1.1074 (4) | 0.0068 (3) | 0.7672 (7) | 0.124 (2) | |
H31A | 1.1803 | 0.0039 | 0.7784 | 0.149* | |
C32 | 1.0720 (5) | 0.0077 (2) | 0.6688 (5) | 0.1147 (18) | |
H32A | 1.1193 | 0.0061 | 0.6127 | 0.138* | |
C33 | 0.9692 (7) | 0.0108 (3) | 0.6510 (5) | 0.142 (2) | |
H33A | 0.9415 | 0.0102 | 0.5826 | 0.171* | |
C34 | 0.9059 (5) | 0.0148 (3) | 0.7356 (10) | 0.156 (4) | |
H34A | 0.8328 | 0.0172 | 0.7258 | 0.188* | |
C35 | 0.9443 (7) | 0.0153 (3) | 0.8297 (8) | 0.148 (3) | |
H35A | 0.8980 | 0.0198 | 0.8862 | 0.177* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0486 (2) | 0.0511 (2) | 0.0401 (2) | −0.00192 (18) | 0.00083 (15) | 0.00375 (17) |
Cl1 | 0.1047 (8) | 0.0798 (7) | 0.1068 (8) | −0.0133 (6) | −0.0161 (6) | −0.0324 (6) |
Cl2 | 0.1095 (8) | 0.0564 (6) | 0.1007 (7) | −0.0018 (5) | 0.0123 (6) | 0.0219 (5) |
O1 | 0.0581 (12) | 0.0522 (12) | 0.0427 (11) | −0.0007 (10) | −0.0030 (9) | 0.0007 (9) |
O2 | 0.0669 (13) | 0.0510 (12) | 0.0460 (11) | −0.0053 (10) | 0.0004 (10) | 0.0024 (9) |
N1 | 0.0478 (14) | 0.0509 (15) | 0.0444 (13) | −0.0027 (12) | −0.0011 (11) | 0.0016 (12) |
N2 | 0.0433 (13) | 0.0513 (14) | 0.0398 (12) | 0.0010 (11) | 0.0038 (10) | 0.0006 (11) |
N3 | 0.0523 (15) | 0.0672 (18) | 0.0436 (14) | −0.0020 (13) | 0.0006 (12) | 0.0054 (13) |
N4 | 0.0534 (14) | 0.0618 (17) | 0.0442 (13) | −0.0011 (14) | 0.0042 (11) | 0.0026 (12) |
N5 | 0.0505 (15) | 0.0617 (18) | 0.0506 (15) | 0.0017 (13) | 0.0019 (12) | 0.0115 (12) |
N6 | 0.209 (7) | 0.154 (5) | 0.108 (4) | −0.013 (5) | 0.019 (4) | −0.014 (3) |
C1 | 0.072 (2) | 0.069 (2) | 0.057 (2) | −0.0036 (18) | −0.0134 (17) | 0.0028 (17) |
C2 | 0.081 (2) | 0.080 (3) | 0.060 (2) | −0.004 (2) | −0.0171 (18) | −0.0077 (19) |
C3 | 0.059 (2) | 0.067 (2) | 0.069 (2) | −0.0057 (17) | 0.0014 (17) | −0.0180 (18) |
C4 | 0.088 (3) | 0.052 (2) | 0.066 (2) | −0.0093 (18) | 0.0058 (19) | −0.0011 (17) |
C5 | 0.077 (2) | 0.059 (2) | 0.0499 (18) | −0.0047 (17) | 0.0016 (16) | −0.0006 (16) |
C6 | 0.0413 (15) | 0.0556 (19) | 0.0458 (16) | −0.0002 (13) | 0.0012 (13) | −0.0006 (14) |
C7 | 0.0363 (14) | 0.0553 (18) | 0.0412 (16) | 0.0010 (13) | 0.0064 (12) | 0.0010 (13) |
C8 | 0.0423 (15) | 0.0549 (19) | 0.0449 (16) | 0.0037 (13) | 0.0062 (12) | 0.0088 (14) |
C9 | 0.071 (2) | 0.065 (2) | 0.059 (2) | −0.0046 (17) | −0.0128 (17) | 0.0122 (16) |
C10 | 0.0421 (16) | 0.0499 (18) | 0.0513 (17) | 0.0039 (13) | 0.0069 (13) | 0.0044 (14) |
C11 | 0.0431 (16) | 0.0532 (19) | 0.0522 (17) | −0.0001 (14) | 0.0091 (13) | −0.0011 (14) |
C12 | 0.062 (2) | 0.059 (2) | 0.060 (2) | −0.0028 (16) | 0.0071 (16) | −0.0052 (16) |
C13 | 0.069 (2) | 0.048 (2) | 0.084 (3) | −0.0052 (16) | 0.0106 (19) | −0.0072 (17) |
C14 | 0.061 (2) | 0.0456 (18) | 0.070 (2) | 0.0053 (15) | 0.0131 (17) | 0.0074 (15) |
C15 | 0.0560 (19) | 0.057 (2) | 0.0581 (19) | 0.0049 (15) | 0.0067 (15) | 0.0062 (15) |
C16 | 0.087 (3) | 0.076 (3) | 0.063 (2) | −0.004 (2) | −0.0080 (19) | 0.0155 (19) |
C17 | 0.110 (3) | 0.108 (4) | 0.071 (3) | 0.007 (3) | −0.014 (2) | 0.034 (3) |
C18 | 0.091 (3) | 0.146 (5) | 0.051 (2) | 0.024 (3) | −0.012 (2) | 0.021 (3) |
C19 | 0.062 (2) | 0.125 (4) | 0.059 (2) | 0.005 (2) | −0.0120 (18) | −0.011 (2) |
C20 | 0.058 (2) | 0.087 (3) | 0.057 (2) | −0.0061 (18) | −0.0009 (16) | −0.0009 (18) |
C21 | 0.072 (2) | 0.065 (2) | 0.092 (3) | −0.0096 (19) | 0.029 (2) | −0.010 (2) |
C22 | 0.075 (3) | 0.092 (3) | 0.112 (3) | −0.022 (2) | 0.042 (2) | −0.013 (3) |
C23 | 0.064 (2) | 0.109 (4) | 0.076 (3) | −0.007 (2) | 0.027 (2) | −0.007 (2) |
C24 | 0.084 (3) | 0.083 (3) | 0.101 (3) | 0.021 (2) | 0.031 (2) | 0.001 (2) |
C25 | 0.068 (2) | 0.065 (2) | 0.080 (2) | 0.0016 (18) | 0.0223 (19) | 0.0099 (19) |
C26 | 0.056 (2) | 0.069 (3) | 0.140 (4) | 0.0044 (19) | 0.022 (2) | 0.025 (2) |
C27 | 0.059 (3) | 0.086 (3) | 0.195 (6) | 0.001 (2) | 0.029 (3) | 0.049 (3) |
C28 | 0.057 (2) | 0.107 (4) | 0.125 (4) | 0.018 (2) | 0.027 (2) | 0.037 (3) |
C29 | 0.064 (3) | 0.088 (3) | 0.157 (4) | 0.018 (2) | 0.026 (3) | 0.000 (3) |
C30 | 0.063 (2) | 0.068 (3) | 0.108 (3) | 0.0004 (19) | 0.012 (2) | 0.003 (2) |
C31 | 0.076 (3) | 0.136 (5) | 0.159 (6) | 0.000 (3) | −0.022 (4) | 0.024 (5) |
C32 | 0.118 (5) | 0.111 (4) | 0.116 (5) | 0.036 (3) | 0.043 (4) | 0.000 (3) |
C33 | 0.156 (7) | 0.150 (6) | 0.120 (5) | 0.032 (5) | −0.044 (5) | −0.046 (4) |
C34 | 0.078 (4) | 0.111 (5) | 0.280 (11) | −0.002 (3) | −0.039 (6) | −0.066 (7) |
C35 | 0.126 (6) | 0.100 (4) | 0.219 (9) | −0.017 (4) | 0.099 (6) | −0.034 (5) |
Geometric parameters (Å, º) top
Ni1—O1 | 2.033 (2) | C12—H12A | 0.9300 |
Ni1—O2 | 1.972 (2) | C13—C14 | 1.371 (4) |
Ni1—N2 | 2.009 (2) | C13—H13A | 0.9300 |
Ni1—N3 | 2.092 (2) | C14—C15 | 1.365 (4) |
Ni1—N4 | 2.183 (2) | C15—H15A | 0.9300 |
Ni1—N5 | 2.174 (2) | C16—C17 | 1.370 (5) |
Cl1—C3 | 1.743 (3) | C16—H16A | 0.9300 |
Cl2—C14 | 1.742 (3) | C17—C18 | 1.364 (6) |
N1—N2 | 1.393 (3) | C17—H17A | 0.9300 |
N1—C7 | 1.309 (4) | C18—C19 | 1.363 (6) |
N2—C8 | 1.299 (4) | C18—H18A | 0.9300 |
O1—C7 | 1.283 (3) | C19—C20 | 1.368 (5) |
O2—C11 | 1.296 (3) | C19—H19A | 0.9300 |
N3—C20 | 1.325 (4) | C20—H20A | 0.9300 |
N3—C16 | 1.326 (4) | C21—C22 | 1.369 (5) |
N4—C25 | 1.306 (4) | C21—H21A | 0.9300 |
N4—C21 | 1.321 (4) | C22—C23 | 1.353 (6) |
N5—C26 | 1.311 (4) | C22—H22A | 0.9300 |
N5—C30 | 1.312 (4) | C23—C24 | 1.357 (5) |
N6—C31 | 1.304 (7) | C23—H23A | 0.9300 |
N6—C35 | 1.312 (8) | C24—C25 | 1.368 (5) |
C1—C6 | 1.378 (4) | C24—H24A | 0.9300 |
C1—C2 | 1.389 (5) | C25—H25A | 0.9300 |
C1—H1B | 0.9300 | C26—C27 | 1.376 (5) |
C2—C3 | 1.357 (5) | C26—H26A | 0.9300 |
C2—H2A | 0.9300 | C27—C28 | 1.333 (6) |
C3—C4 | 1.361 (5) | C27—H27A | 0.9300 |
C4—C5 | 1.382 (4) | C28—C29 | 1.357 (6) |
C4—H4A | 0.9300 | C28—H28A | 0.9300 |
C5—C6 | 1.365 (4) | C29—C30 | 1.367 (5) |
C5—H5A | 0.9300 | C29—H29A | 0.9300 |
C6—C7 | 1.490 (4) | C30—H30A | 0.9300 |
C8—C10 | 1.470 (4) | C31—C32 | 1.318 (7) |
C8—C9 | 1.508 (4) | C31—H31A | 0.9300 |
C9—H9A | 0.9600 | C32—C33 | 1.316 (7) |
C9—H9B | 0.9600 | C32—H32A | 0.9300 |
C9—H9C | 0.9600 | C33—C34 | 1.341 (9) |
C10—C15 | 1.411 (4) | C33—H33A | 0.9300 |
C10—C11 | 1.427 (4) | C34—C35 | 1.281 (10) |
C11—C12 | 1.406 (4) | C34—H34A | 0.9300 |
C12—C13 | 1.364 (4) | C35—H35A | 0.9300 |
O1—Ni1—N3 | 96.73 (9) | C12—C13—C14 | 118.8 (3) |
O1—Ni1—N4 | 87.38 (9) | C12—C13—H13A | 120.6 |
O1—Ni1—N5 | 89.96 (9) | C14—C13—H13A | 120.6 |
O2—Ni1—N2 | 90.31 (9) | C15—C14—C13 | 120.3 (3) |
O2—Ni1—N3 | 92.79 (10) | C15—C14—Cl2 | 120.4 (3) |
O2—Ni1—O1 | 170.27 (8) | C13—C14—Cl2 | 119.2 (3) |
O2—Ni1—N4 | 90.99 (9) | C14—C15—C10 | 122.6 (3) |
O2—Ni1—N5 | 92.79 (10) | C14—C15—H15A | 118.7 |
N2—Ni1—O1 | 80.19 (9) | C10—C15—H15A | 118.7 |
N2—Ni1—N3 | 176.86 (10) | N3—C16—C17 | 123.0 (4) |
N2—Ni1—N5 | 93.92 (9) | N3—C16—H16A | 118.5 |
N2—Ni1—N4 | 92.53 (9) | C17—C16—H16A | 118.5 |
N3—Ni1—N5 | 85.43 (9) | C18—C17—C16 | 118.2 (4) |
N3—Ni1—N4 | 87.91 (9) | C18—C17—H17A | 120.9 |
N5—Ni1—N4 | 172.50 (9) | C16—C17—H17A | 120.9 |
C7—O1—Ni1 | 108.58 (17) | C19—C18—C17 | 119.7 (4) |
C11—O2—Ni1 | 127.18 (19) | C19—C18—H18A | 120.2 |
C7—N1—N2 | 111.6 (2) | C17—C18—H18A | 120.2 |
C8—N2—N1 | 116.9 (2) | C18—C19—C20 | 118.4 (4) |
C8—N2—Ni1 | 130.3 (2) | C18—C19—H19A | 120.8 |
N1—N2—Ni1 | 112.72 (18) | C20—C19—H19A | 120.8 |
C20—N3—C16 | 117.7 (3) | N3—C20—C19 | 123.0 (4) |
C20—N3—Ni1 | 121.1 (2) | N3—C20—H20A | 118.5 |
C16—N3—Ni1 | 121.1 (2) | C19—C20—H20A | 118.5 |
C25—N4—C21 | 116.8 (3) | N4—C21—C22 | 123.4 (4) |
C25—N4—Ni1 | 121.0 (2) | N4—C21—H21A | 118.3 |
C21—N4—Ni1 | 122.2 (2) | C22—C21—H21A | 118.3 |
C26—N5—C30 | 116.0 (3) | C23—C22—C21 | 119.2 (4) |
C26—N5—Ni1 | 122.7 (3) | C23—C22—H22A | 120.4 |
C30—N5—Ni1 | 121.0 (2) | C21—C22—H22A | 120.4 |
C31—N6—C35 | 115.7 (6) | C22—C23—C24 | 117.6 (4) |
C6—C1—C2 | 120.7 (3) | C22—C23—H23A | 121.2 |
C6—C1—H1B | 119.7 | C24—C23—H23A | 121.2 |
C2—C1—H1B | 119.7 | C23—C24—C25 | 119.8 (4) |
C3—C2—C1 | 119.5 (3) | C23—C24—H24A | 120.1 |
C3—C2—H2A | 120.2 | C25—C24—H24A | 120.1 |
C1—C2—H2A | 120.2 | N4—C25—C24 | 123.1 (4) |
C2—C3—C4 | 121.1 (3) | N4—C25—H25A | 118.4 |
C2—C3—Cl1 | 119.6 (3) | C24—C25—H25A | 118.4 |
C4—C3—Cl1 | 119.3 (3) | N5—C26—C27 | 123.0 (4) |
C3—C4—C5 | 118.7 (3) | N5—C26—H26A | 118.5 |
C3—C4—H4A | 120.7 | C27—C26—H26A | 118.5 |
C5—C4—H4A | 120.7 | C28—C27—C26 | 119.9 (4) |
C6—C5—C4 | 122.1 (3) | C28—C27—H27A | 120.0 |
C6—C5—H5A | 119.0 | C26—C27—H27A | 120.0 |
C4—C5—H5A | 119.0 | C27—C28—C29 | 118.3 (4) |
C5—C6—C1 | 117.9 (3) | C27—C28—H28A | 120.8 |
C5—C6—C7 | 120.3 (3) | C29—C28—H28A | 120.8 |
C1—C6—C7 | 121.7 (3) | C28—C29—C30 | 118.2 (4) |
O1—C7—N1 | 126.8 (3) | C28—C29—H29A | 120.9 |
O1—C7—C6 | 117.5 (3) | C30—C29—H29A | 120.9 |
N1—C7—C6 | 115.7 (3) | N5—C30—C29 | 124.6 (4) |
N2—C8—C10 | 120.3 (3) | N5—C30—H30A | 117.7 |
N2—C8—C9 | 120.6 (3) | C29—C30—H30A | 117.7 |
C10—C8—C9 | 119.1 (3) | N6—C31—C32 | 123.8 (5) |
C8—C9—H9A | 109.5 | N6—C31—H31A | 118.1 |
C8—C9—H9B | 109.5 | C32—C31—H31A | 118.1 |
H9A—C9—H9B | 109.5 | C33—C32—C31 | 119.2 (5) |
C8—C9—H9C | 109.5 | C33—C32—H32A | 120.4 |
H9A—C9—H9C | 109.5 | C31—C32—H32A | 120.4 |
H9B—C9—H9C | 109.5 | C32—C33—C34 | 117.2 (6) |
C15—C10—C11 | 117.5 (3) | C32—C33—H33A | 121.4 |
C15—C10—C8 | 117.6 (3) | C34—C33—H33A | 121.4 |
C11—C10—C8 | 124.9 (3) | C35—C34—C33 | 121.2 (7) |
O2—C11—C12 | 117.3 (3) | C35—C34—H34A | 119.4 |
O2—C11—C10 | 125.6 (3) | C33—C34—H34A | 119.4 |
C12—C11—C10 | 117.1 (3) | C34—C35—N6 | 122.7 (7) |
C13—C12—C11 | 123.8 (3) | C34—C35—H35A | 118.6 |
C13—C12—H12A | 118.1 | N6—C35—H35A | 118.6 |
C11—C12—H12A | 118.1 | ||
O2—Ni1—O1—C7 | −9.8 (5) | Ni1—O1—C7—N1 | −2.1 (3) |
N2—Ni1—O1—C7 | 2.70 (17) | Ni1—O1—C7—C6 | 178.10 (18) |
N3—Ni1—O1—C7 | −177.91 (17) | N2—N1—C7—O1 | −0.6 (4) |
N5—Ni1—O1—C7 | 96.69 (17) | N2—N1—C7—C6 | 179.3 (2) |
N4—Ni1—O1—C7 | −90.33 (18) | C5—C6—C7—O1 | −6.9 (4) |
N2—Ni1—O2—C11 | 11.7 (2) | C1—C6—C7—O1 | 172.7 (3) |
O1—Ni1—O2—C11 | 24.0 (6) | C5—C6—C7—N1 | 173.2 (3) |
N3—Ni1—O2—C11 | −167.8 (2) | C1—C6—C7—N1 | −7.2 (4) |
N5—Ni1—O2—C11 | −82.3 (2) | N1—N2—C8—C10 | 176.9 (2) |
N4—Ni1—O2—C11 | 104.2 (2) | Ni1—N2—C8—C10 | −4.5 (4) |
C7—N1—N2—C8 | −178.2 (2) | N1—N2—C8—C9 | −2.5 (4) |
C7—N1—N2—Ni1 | 3.0 (3) | Ni1—N2—C8—C9 | 176.1 (2) |
O2—Ni1—N2—C8 | −3.9 (2) | N2—C8—C10—C15 | −170.4 (3) |
O1—Ni1—N2—C8 | 178.2 (3) | C9—C8—C10—C15 | 9.1 (4) |
N3—Ni1—N2—C8 | 167.0 (15) | N2—C8—C10—C11 | 8.8 (4) |
N5—Ni1—N2—C8 | 88.9 (2) | C9—C8—C10—C11 | −171.7 (3) |
N4—Ni1—N2—C8 | −94.9 (2) | Ni1—O2—C11—C12 | 168.8 (2) |
O2—Ni1—N2—N1 | 174.77 (17) | Ni1—O2—C11—C10 | −11.3 (4) |
O1—Ni1—N2—N1 | −3.13 (16) | C15—C10—C11—O2 | 178.5 (3) |
N3—Ni1—N2—N1 | −14.3 (17) | C8—C10—C11—O2 | −0.7 (4) |
N5—Ni1—N2—N1 | −92.41 (18) | C15—C10—C11—C12 | −1.6 (4) |
N4—Ni1—N2—N1 | 83.77 (18) | C8—C10—C11—C12 | 179.2 (3) |
O2—Ni1—N3—C20 | 10.3 (2) | O2—C11—C12—C13 | −178.5 (3) |
N2—Ni1—N3—C20 | −160.6 (15) | C10—C11—C12—C13 | 1.5 (5) |
O1—Ni1—N3—C20 | −171.7 (2) | C11—C12—C13—C14 | −0.2 (5) |
N5—Ni1—N3—C20 | −82.3 (2) | C12—C13—C14—C15 | −1.0 (5) |
N4—Ni1—N3—C20 | 101.2 (2) | C12—C13—C14—Cl2 | 178.9 (3) |
O2—Ni1—N3—C16 | −171.6 (3) | C13—C14—C15—C10 | 0.8 (5) |
N2—Ni1—N3—C16 | 17.5 (17) | Cl2—C14—C15—C10 | −179.0 (2) |
O1—Ni1—N3—C16 | 6.4 (3) | C11—C10—C15—C14 | 0.5 (4) |
N5—Ni1—N3—C16 | 95.8 (3) | C8—C10—C15—C14 | 179.7 (3) |
N4—Ni1—N3—C16 | −80.7 (3) | C20—N3—C16—C17 | 0.3 (5) |
O2—Ni1—N4—C25 | −12.0 (3) | Ni1—N3—C16—C17 | −177.9 (3) |
N2—Ni1—N4—C25 | 78.4 (3) | N3—C16—C17—C18 | 0.2 (6) |
O1—Ni1—N4—C25 | 158.4 (3) | C16—C17—C18—C19 | −0.3 (7) |
N3—Ni1—N4—C25 | −104.7 (3) | C17—C18—C19—C20 | 0.0 (6) |
N5—Ni1—N4—C25 | −132.2 (7) | C16—N3—C20—C19 | −0.6 (5) |
O2—Ni1—N4—C21 | 166.6 (3) | Ni1—N3—C20—C19 | 177.6 (3) |
N2—Ni1—N4—C21 | −103.1 (3) | C18—C19—C20—N3 | 0.5 (6) |
O1—Ni1—N4—C21 | −23.0 (3) | C25—N4—C21—C22 | 0.9 (6) |
N3—Ni1—N4—C21 | 73.8 (3) | Ni1—N4—C21—C22 | −177.7 (3) |
N5—Ni1—N4—C21 | 46.3 (9) | N4—C21—C22—C23 | −2.0 (7) |
O2—Ni1—N5—C26 | 5.5 (3) | C21—C22—C23—C24 | 1.9 (7) |
N2—Ni1—N5—C26 | −85.0 (3) | C22—C23—C24—C25 | −1.0 (7) |
O1—Ni1—N5—C26 | −165.1 (3) | C21—N4—C25—C24 | 0.1 (6) |
N3—Ni1—N5—C26 | 98.1 (3) | Ni1—N4—C25—C24 | 178.7 (3) |
N4—Ni1—N5—C26 | 125.7 (8) | C23—C24—C25—N4 | −0.1 (6) |
O2—Ni1—N5—C30 | −168.6 (3) | C30—N5—C26—C27 | 0.4 (6) |
N2—Ni1—N5—C30 | 100.9 (3) | Ni1—N5—C26—C27 | −174.0 (4) |
O1—Ni1—N5—C30 | 20.7 (3) | N5—C26—C27—C28 | −1.2 (8) |
N3—Ni1—N5—C30 | −76.0 (3) | C26—C27—C28—C29 | 1.1 (8) |
N4—Ni1—N5—C30 | −48.4 (9) | C27—C28—C29—C30 | −0.2 (7) |
C6—C1—C2—C3 | −0.1 (5) | C26—N5—C30—C29 | 0.5 (6) |
C1—C2—C3—C4 | −0.8 (6) | Ni1—N5—C30—C29 | 175.0 (3) |
C1—C2—C3—Cl1 | 178.5 (3) | C28—C29—C30—N5 | −0.6 (7) |
C2—C3—C4—C5 | 0.5 (5) | C35—N6—C31—C32 | −1.7 (10) |
Cl1—C3—C4—C5 | −178.8 (3) | N6—C31—C32—C33 | −0.9 (10) |
C3—C4—C5—C6 | 0.6 (5) | C31—C32—C33—C34 | 1.9 (10) |
C4—C5—C6—C1 | −1.4 (5) | C32—C33—C34—C35 | −0.3 (11) |
C4—C5—C6—C7 | 178.2 (3) | C33—C34—C35—N6 | −2.6 (12) |
C2—C1—C6—C5 | 1.2 (5) | C31—N6—C35—C34 | 3.5 (11) |
C2—C1—C6—C7 | −178.4 (3) |