metal-organic compounds
The VIV atom in the title compound, [V(C18H12N2O4)2]·CH2Cl2·0.5C6H14, which crystallizes as a dichloromethane hexane hemisolvate, exists in a trigonal prismatic geometry. The hexane molecule lies across an inversion center and both solvent molecules are disordered.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805004174/ci6524sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805004174/ci6524Isup2.hkl |
CCDC reference: 269410
Computing details top
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
bis(2-oxidonaphthalene-1-carbaldehyde benzoylhydrazonato)vanadium(IV)
dichloromethane hexane hemisolvate top
Crystal data top
[V(C18H12N2O4)2]·CH2Cl2·0.5C6H14 | Z = 2 |
Mr = 755.54 | F(000) = 780 |
Triclinic, P1 | Dx = 1.404 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 12.598 (3) Å | Cell parameters from 15371 reflections |
b = 13.021 (3) Å | θ = 3.0–27.5° |
c = 13.652 (3) Å | µ = 0.48 mm−1 |
α = 116.04 (3)° | T = 295 K |
β = 101.84 (3)° | Prism, black |
γ = 106.21 (3)° | 0.38 × 0.26 × 0.18 mm |
V = 1787.2 (6) Å3 |
Data collection top
Rigaku R-AXIS RAPID diffractometer | 8039 independent reflections |
Radiation source: fine-focus sealed tube | 5896 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
ω scans | θmax = 27.5°, θmin = 3.0° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −15→16 |
Tmin = 0.758, Tmax = 0.919 | k = −16→16 |
17362 measured reflections | l = −17→17 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.174 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.1036P)2 + 0.4047P] where P = (Fo2 + 2Fc2)/3 |
8039 reflections | (Δ/σ)max = 0.001 |
474 parameters | Δρmax = 0.88 e Å−3 |
39 restraints | Δρmin = −0.94 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | Occ. (<1) | |
V1 | 0.37764 (4) | 0.24017 (4) | 0.54285 (4) | 0.0362 (1) | |
Cl1 | 0.2954 (1) | 0.2548 (1) | 0.1674 (2) | 0.1372 (7) | |
Cl2 | 0.5184 (1) | 0.2519 (1) | 0.2638 (2) | 0.1135 (5) | |
O1 | 0.3556 (2) | 0.3785 (2) | 0.5416 (2) | 0.0429 (4) | |
O2 | 0.3951 (2) | 0.1850 (2) | 0.6520 (2) | 0.0445 (4) | |
O3 | 0.5385 (2) | 0.3629 (2) | 0.6375 (2) | 0.0446 (4) | |
O4 | 0.2768 (2) | 0.1391 (2) | 0.3795 (2) | 0.0448 (4) | |
N1 | 0.2245 (2) | 0.2143 (2) | 0.5762 (2) | 0.0413 (5) | |
N2 | 0.2068 (2) | 0.1598 (2) | 0.6427 (2) | 0.0473 (5) | |
N3 | 0.4599 (2) | 0.1316 (2) | 0.4599 (2) | 0.0383 (4) | |
N4 | 0.3947 (2) | 0.0350 (2) | 0.3433 (2) | 0.0433 (5) | |
C1 | 0.2567 (2) | 0.3806 (2) | 0.4907 (2) | 0.0402 (5) | |
C2 | 0.2660 (3) | 0.4631 (3) | 0.4476 (3) | 0.0494 (6) | |
C3 | 0.1671 (3) | 0.4722 (3) | 0.3978 (3) | 0.0524 (7) | |
C4 | 0.0522 (3) | 0.4026 (3) | 0.3868 (2) | 0.0456 (6) | |
C5 | −0.0489 (3) | 0.4144 (3) | 0.3353 (3) | 0.0544 (7) | |
C6 | −0.1586 (3) | 0.3498 (3) | 0.3276 (3) | 0.0619 (8) | |
C7 | −0.1714 (3) | 0.2717 (3) | 0.3721 (3) | 0.0631 (8) | |
C8 | −0.0755 (3) | 0.2566 (3) | 0.4216 (3) | 0.0552 (7) | |
C9 | 0.0398 (2) | 0.3218 (2) | 0.4311 (2) | 0.0422 (6) | |
C10 | 0.1447 (2) | 0.3106 (2) | 0.4837 (2) | 0.0408 (5) | |
C11 | 0.1379 (2) | 0.2415 (2) | 0.5392 (2) | 0.0430 (6) | |
C12 | 0.3035 (2) | 0.1486 (2) | 0.6801 (2) | 0.0423 (6) | |
C13 | 0.3148 (3) | 0.0978 (3) | 0.7569 (2) | 0.0466 (6) | |
C14 | 0.2231 (3) | 0.0632 (3) | 0.7937 (3) | 0.0601 (8) | |
C15 | 0.2350 (4) | 0.0173 (4) | 0.8665 (3) | 0.0769 (11) | |
C16 | 0.3396 (5) | 0.0054 (4) | 0.9044 (4) | 0.0836 (12) | |
C17 | 0.4286 (4) | 0.0369 (4) | 0.8669 (3) | 0.0771 (11) | |
C18 | 0.4175 (3) | 0.0830 (3) | 0.7937 (3) | 0.0574 (7) | |
C19 | 0.6332 (2) | 0.3491 (2) | 0.6799 (2) | 0.0408 (5) | |
C20 | 0.7212 (3) | 0.4514 (3) | 0.7909 (2) | 0.0503 (7) | |
C21 | 0.8278 (3) | 0.4503 (3) | 0.8332 (2) | 0.0540 (7) | |
C22 | 0.8555 (3) | 0.3482 (3) | 0.7705 (2) | 0.0462 (6) | |
C23 | 0.9681 (3) | 0.3506 (3) | 0.8135 (3) | 0.0588 (8) | |
C24 | 0.9944 (3) | 0.2515 (3) | 0.7538 (3) | 0.0612 (8) | |
C25 | 0.9087 (3) | 0.1472 (3) | 0.6480 (3) | 0.0547 (7) | |
C26 | 0.7987 (3) | 0.1418 (3) | 0.6022 (3) | 0.0473 (6) | |
C27 | 0.7683 (2) | 0.2424 (2) | 0.6611 (2) | 0.0411 (5) | |
C28 | 0.6542 (2) | 0.2426 (2) | 0.6160 (2) | 0.0378 (5) | |
C29 | 0.5679 (2) | 0.1435 (2) | 0.5030 (2) | 0.0412 (6) | |
C30 | 0.2973 (2) | 0.0462 (2) | 0.3083 (2) | 0.0397 (5) | |
C31 | 0.2076 (2) | −0.0431 (2) | 0.1871 (2) | 0.0434 (6) | |
C32 | 0.2248 (3) | −0.1424 (3) | 0.1084 (3) | 0.0600 (8) | |
C33 | 0.1400 (4) | −0.2246 (4) | −0.0052 (3) | 0.0757 (11) | |
C34 | 0.0381 (4) | −0.2099 (4) | −0.0404 (3) | 0.0737 (10) | |
C35 | 0.0206 (3) | −0.1130 (3) | 0.0377 (3) | 0.0718 (10) | |
C36 | 0.1046 (3) | −0.0290 (3) | 0.1521 (3) | 0.0589 (8) | |
C37 | 0.4307 (4) | 0.3359 (4) | 0.2845 (4) | 0.0773 (18) | 0.815 (12) |
C37' | 0.4530 (5) | 0.337 (1) | 0.218 (2) | 0.0773 (18) | 0.185 (12) |
C38 | 0.4838 (9) | 0.543 (1) | 0.981 (2) | 0.208 (6) | 0.741 (13) |
C39 | 0.3534 (8) | 0.494 (1) | 0.923 (1) | 0.189 (6) | 0.741 (13) |
C40 | 0.312 (1) | 0.549 (1) | 0.858 (1) | 0.177 (6) | 0.741 (13) |
C38' | 0.440 (2) | 0.465 (2) | 0.947 (3) | 0.208 (6) | 0.259 (13) |
C39' | 0.415 (3) | 0.546 (4) | 0.900 (3) | 0.189 (6) | 0.259 (13) |
C40' | 0.331 (3) | 0.597 (4) | 0.953 (3) | 0.177 (6) | 0.259 (13) |
H2 | 0.3401 | 0.5109 | 0.4537 | 0.059* | |
H3 | 0.1751 | 0.5263 | 0.3698 | 0.063* | |
H5 | −0.0405 | 0.4673 | 0.3060 | 0.065* | |
H6 | −0.2249 | 0.3579 | 0.2927 | 0.074* | |
H7 | −0.2464 | 0.2289 | 0.3683 | 0.076* | |
H8 | −0.0866 | 0.2024 | 0.4494 | 0.066* | |
H11 | 0.0676 | 0.2134 | 0.5504 | 0.052* | |
H14 | 0.1532 | 0.0713 | 0.7686 | 0.072* | |
H15 | 0.1732 | −0.0059 | 0.8906 | 0.092* | |
H16 | 0.3488 | −0.0239 | 0.9552 | 0.100* | |
H17 | 0.4978 | 0.0271 | 0.8910 | 0.093* | |
H18 | 0.4791 | 0.1044 | 0.7689 | 0.069* | |
H20 | 0.7055 | 0.5196 | 0.8349 | 0.060* | |
H21 | 0.8845 | 0.5188 | 0.9057 | 0.065* | |
H23 | 1.0259 | 0.4211 | 0.8842 | 0.071* | |
H24 | 1.0691 | 0.2541 | 0.7838 | 0.073* | |
H25 | 0.9263 | 0.0796 | 0.6072 | 0.066* | |
H26 | 0.7429 | 0.0705 | 0.5309 | 0.057* | |
H29 | 0.5899 | 0.0825 | 0.4564 | 0.049* | |
H32 | 0.2930 | −0.1541 | 0.1316 | 0.072* | |
H33 | 0.1523 | −0.2907 | −0.0584 | 0.091* | |
H34 | −0.0185 | −0.2657 | −0.1168 | 0.088* | |
H35 | −0.0485 | −0.1027 | 0.0142 | 0.086* | |
H36 | 0.0913 | 0.0365 | 0.2049 | 0.071* | |
H37a | 0.4167 | 0.3523 | 0.3561 | 0.093* | 0.815 (12) |
H37b | 0.4731 | 0.4164 | 0.2939 | 0.093* | 0.815 (12) |
H37c | 0.4801 | 0.4221 | 0.2841 | 0.093* | 0.185 (12) |
H37d | 0.4753 | 0.3410 | 0.1559 | 0.093* | 0.185 (12) |
H38a | 0.5139 | 0.6268 | 1.0499 | 0.250* | 0.741 (13) |
H38b | 0.5215 | 0.5488 | 0.9275 | 0.250* | 0.741 (13) |
H39a | 0.3222 | 0.4038 | 0.8684 | 0.227* | 0.741 (13) |
H39b | 0.3191 | 0.5066 | 0.9825 | 0.227* | 0.741 (13) |
H40a | 0.2378 | 0.5516 | 0.8645 | 0.265* | 0.741 (13) |
H40b | 0.2990 | 0.4978 | 0.7770 | 0.265* | 0.741 (13) |
H40c | 0.3703 | 0.6323 | 0.8913 | 0.265* | 0.741 (13) |
H38c | 0.4412 | 0.3914 | 0.8846 | 0.250* | 0.259 (13) |
H38d | 0.3762 | 0.4361 | 0.9708 | 0.250* | 0.259 (13) |
H39c | 0.3781 | 0.4964 | 0.8149 | 0.227* | 0.259 (13) |
H39d | 0.4894 | 0.6155 | 0.9232 | 0.227* | 0.259 (13) |
H40d | 0.3217 | 0.5760 | 1.0103 | 0.265* | 0.259 (13) |
H40e | 0.2548 | 0.5608 | 0.8911 | 0.265* | 0.259 (13) |
H40f | 0.3647 | 0.6873 | 0.9896 | 0.265* | 0.259 (13) |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
V1 | 0.0339 (2) | 0.0373 (2) | 0.0388 (2) | 0.01616 (17) | 0.01555 (17) | 0.01949 (18) |
Cl1 | 0.0946 (10) | 0.0776 (7) | 0.1512 (13) | 0.0296 (7) | −0.0188 (9) | 0.0242 (8) |
Cl2 | 0.0831 (8) | 0.1124 (9) | 0.1573 (13) | 0.0533 (7) | 0.0419 (8) | 0.0751 (9) |
O1 | 0.0375 (10) | 0.0402 (9) | 0.0534 (10) | 0.0175 (8) | 0.0181 (8) | 0.0254 (8) |
O2 | 0.0406 (10) | 0.0564 (11) | 0.0474 (10) | 0.0245 (9) | 0.0204 (8) | 0.0316 (9) |
O3 | 0.0380 (10) | 0.0377 (9) | 0.0503 (10) | 0.0150 (8) | 0.0137 (8) | 0.0189 (8) |
O4 | 0.0439 (10) | 0.0467 (10) | 0.0414 (9) | 0.0237 (8) | 0.0146 (8) | 0.0192 (8) |
N1 | 0.0424 (12) | 0.0465 (11) | 0.0481 (12) | 0.0224 (10) | 0.0228 (10) | 0.0303 (10) |
N2 | 0.0474 (13) | 0.0603 (14) | 0.0588 (13) | 0.0300 (11) | 0.0292 (11) | 0.0421 (12) |
N3 | 0.0336 (11) | 0.0383 (10) | 0.0395 (10) | 0.0137 (9) | 0.0149 (9) | 0.0182 (9) |
N4 | 0.0381 (12) | 0.0406 (11) | 0.0414 (11) | 0.0149 (9) | 0.0150 (9) | 0.0150 (9) |
C1 | 0.0421 (14) | 0.0397 (12) | 0.0409 (12) | 0.0206 (11) | 0.0192 (11) | 0.0194 (11) |
C2 | 0.0533 (17) | 0.0522 (15) | 0.0594 (16) | 0.0262 (13) | 0.0324 (14) | 0.0353 (14) |
C3 | 0.066 (2) | 0.0580 (16) | 0.0557 (16) | 0.0351 (15) | 0.0316 (15) | 0.0382 (14) |
C4 | 0.0546 (17) | 0.0506 (14) | 0.0367 (12) | 0.0289 (13) | 0.0193 (12) | 0.0221 (11) |
C5 | 0.065 (2) | 0.0632 (17) | 0.0461 (14) | 0.0374 (16) | 0.0203 (14) | 0.0317 (14) |
C6 | 0.0544 (19) | 0.075 (2) | 0.0544 (17) | 0.0376 (17) | 0.0112 (14) | 0.0303 (16) |
C7 | 0.0474 (18) | 0.0660 (19) | 0.069 (2) | 0.0233 (15) | 0.0136 (15) | 0.0342 (17) |
C8 | 0.0476 (17) | 0.0583 (17) | 0.0636 (18) | 0.0233 (14) | 0.0182 (14) | 0.0360 (15) |
C9 | 0.0419 (14) | 0.0439 (13) | 0.0389 (12) | 0.0208 (11) | 0.0140 (11) | 0.0193 (11) |
C10 | 0.0401 (14) | 0.0429 (13) | 0.0413 (12) | 0.0200 (11) | 0.0165 (11) | 0.0217 (11) |
C11 | 0.0391 (14) | 0.0486 (14) | 0.0510 (14) | 0.0221 (11) | 0.0228 (12) | 0.0291 (12) |
C12 | 0.0476 (15) | 0.0442 (13) | 0.0412 (12) | 0.0240 (12) | 0.0224 (11) | 0.0221 (11) |
C13 | 0.0580 (17) | 0.0482 (14) | 0.0420 (13) | 0.0295 (13) | 0.0226 (12) | 0.0245 (12) |
C14 | 0.073 (2) | 0.072 (2) | 0.0701 (19) | 0.0443 (18) | 0.0425 (18) | 0.0495 (18) |
C15 | 0.104 (3) | 0.093 (3) | 0.080 (2) | 0.054 (2) | 0.058 (2) | 0.063 (2) |
C16 | 0.114 (4) | 0.103 (3) | 0.076 (2) | 0.059 (3) | 0.041 (2) | 0.069 (2) |
C17 | 0.085 (3) | 0.093 (3) | 0.072 (2) | 0.050 (2) | 0.021 (2) | 0.055 (2) |
C18 | 0.061 (2) | 0.0697 (19) | 0.0545 (16) | 0.0356 (16) | 0.0223 (15) | 0.0376 (15) |
C19 | 0.0354 (13) | 0.0416 (13) | 0.0438 (13) | 0.0128 (10) | 0.0149 (11) | 0.0234 (11) |
C20 | 0.0535 (17) | 0.0459 (14) | 0.0440 (14) | 0.0197 (13) | 0.0164 (13) | 0.0196 (12) |
C21 | 0.0483 (17) | 0.0578 (16) | 0.0402 (13) | 0.0150 (13) | 0.0074 (12) | 0.0221 (13) |
C22 | 0.0409 (15) | 0.0526 (15) | 0.0453 (13) | 0.0165 (12) | 0.0136 (11) | 0.0292 (12) |
C23 | 0.0442 (17) | 0.073 (2) | 0.0531 (16) | 0.0186 (15) | 0.0101 (13) | 0.0356 (16) |
C24 | 0.0405 (16) | 0.083 (2) | 0.076 (2) | 0.0285 (16) | 0.0203 (15) | 0.0537 (19) |
C25 | 0.0470 (17) | 0.0629 (17) | 0.0726 (19) | 0.0290 (14) | 0.0300 (15) | 0.0432 (16) |
C26 | 0.0399 (15) | 0.0500 (14) | 0.0579 (16) | 0.0196 (12) | 0.0211 (12) | 0.0316 (13) |
C27 | 0.0350 (13) | 0.0489 (14) | 0.0466 (13) | 0.0160 (11) | 0.0168 (11) | 0.0311 (12) |
C28 | 0.0327 (13) | 0.0424 (13) | 0.0413 (12) | 0.0146 (10) | 0.0153 (10) | 0.0244 (11) |
C29 | 0.0361 (13) | 0.0408 (12) | 0.0452 (13) | 0.0168 (10) | 0.0176 (11) | 0.0202 (11) |
C30 | 0.0371 (13) | 0.0400 (12) | 0.0417 (13) | 0.0134 (10) | 0.0173 (11) | 0.0220 (11) |
C31 | 0.0413 (14) | 0.0436 (13) | 0.0394 (13) | 0.0127 (11) | 0.0147 (11) | 0.0207 (11) |
C32 | 0.0523 (18) | 0.0624 (18) | 0.0486 (16) | 0.0238 (15) | 0.0160 (14) | 0.0180 (14) |
C33 | 0.076 (3) | 0.067 (2) | 0.0481 (16) | 0.0282 (19) | 0.0149 (17) | 0.0078 (16) |
C34 | 0.068 (2) | 0.068 (2) | 0.0427 (16) | 0.0120 (18) | 0.0003 (15) | 0.0161 (16) |
C35 | 0.057 (2) | 0.071 (2) | 0.0581 (19) | 0.0225 (17) | −0.0030 (16) | 0.0240 (17) |
C36 | 0.0519 (18) | 0.0565 (17) | 0.0500 (16) | 0.0215 (14) | 0.0072 (14) | 0.0200 (14) |
C37 | 0.071 (3) | 0.066 (3) | 0.079 (3) | 0.028 (2) | 0.026 (2) | 0.027 (2) |
C37' | 0.071 (3) | 0.066 (3) | 0.079 (3) | 0.028 (2) | 0.026 (2) | 0.027 (2) |
C38 | 0.136 (11) | 0.170 (13) | 0.259 (16) | 0.037 (9) | −0.008 (9) | 0.119 (13) |
C39 | 0.135 (11) | 0.219 (14) | 0.245 (14) | 0.073 (10) | 0.054 (10) | 0.157 (11) |
C40 | 0.142 (8) | 0.212 (12) | 0.208 (13) | 0.081 (9) | 0.021 (10) | 0.152 (13) |
C38' | 0.136 (11) | 0.170 (13) | 0.259 (16) | 0.037 (9) | −0.008 (9) | 0.119 (13) |
C39' | 0.135 (11) | 0.219 (14) | 0.245 (14) | 0.073 (10) | 0.054 (10) | 0.157 (11) |
C40' | 0.142 (8) | 0.212 (12) | 0.208 (13) | 0.081 (9) | 0.021 (10) | 0.152 (13) |
Geometric parameters (Å, º) top
V1—O1 | 1.904 (2) | C31—C32 | 1.381 (4) |
V1—O2 | 1.917 (2) | C32—C33 | 1.384 (5) |
V1—O3 | 1.906 (2) | C33—C34 | 1.371 (5) |
V1—O4 | 1.910 (2) | C34—C35 | 1.359 (5) |
V1—N1 | 2.043 (2) | C35—C36 | 1.389 (4) |
V1—N3 | 2.061 (2) | C38—C39 | 1.473 (9) |
Cl1—C37 | 1.723 (4) | C38—C38i | 1.533 (9) |
Cl1—C37' | 1.779 (5) | C39—C40 | 1.459 (8) |
Cl2—C37 | 1.741 (4) | C38'—C39' | 1.528 (10) |
Cl2—C37' | 1.786 (5) | C38'—C38'i | 1.533 (10) |
O1—C1 | 1.310 (3) | C39'—C40' | 1.538 (10) |
O2—C12 | 1.319 (3) | C2—H2 | 0.93 |
O3—C19 | 1.311 (3) | C3—H3 | 0.93 |
O4—C30 | 1.312 (3) | C5—H5 | 0.93 |
N1—C11 | 1.312 (3) | C6—H6 | 0.93 |
N1—N2 | 1.391 (3) | C7—H7 | 0.93 |
N2—C12 | 1.294 (3) | C8—H8 | 0.93 |
N3—C29 | 1.301 (3) | C11—H11 | 0.93 |
N3—N4 | 1.385 (3) | C14—H14 | 0.93 |
N4—C30 | 1.293 (3) | C15—H15 | 0.93 |
C1—C10 | 1.407 (4) | C16—H16 | 0.93 |
C1—C2 | 1.424 (4) | C17—H17 | 0.93 |
C2—C3 | 1.354 (4) | C18—H18 | 0.93 |
C3—C4 | 1.413 (4) | C20—H20 | 0.93 |
C4—C5 | 1.407 (4) | C21—H21 | 0.93 |
C4—C9 | 1.415 (4) | C23—H23 | 0.93 |
C5—C6 | 1.357 (5) | C24—H24 | 0.93 |
C6—C7 | 1.386 (5) | C25—H25 | 0.93 |
C7—C8 | 1.366 (4) | C26—H26 | 0.93 |
C8—C9 | 1.409 (4) | C29—H29 | 0.93 |
C9—C10 | 1.448 (4) | C32—H32 | 0.93 |
C10—C11 | 1.404 (4) | C33—H33 | 0.93 |
C12—C13 | 1.468 (4) | C34—H34 | 0.93 |
C13—C18 | 1.385 (4) | C35—H35 | 0.93 |
C13—C14 | 1.391 (4) | C36—H36 | 0.93 |
C14—C15 | 1.372 (5) | C37—H37a | 0.97 |
C15—C16 | 1.390 (6) | C37—H37b | 0.97 |
C16—C17 | 1.360 (6) | C37'—H37c | 0.97 |
C17—C18 | 1.377 (5) | C37'—H37d | 0.97 |
C19—C28 | 1.411 (4) | C38—H38a | 0.97 |
C19—C20 | 1.419 (4) | C38—H38b | 0.97 |
C20—C21 | 1.355 (4) | C39—H39a | 0.97 |
C21—C22 | 1.417 (4) | C39—H39b | 0.97 |
C22—C23 | 1.405 (4) | C40—H40a | 0.96 |
C22—C27 | 1.418 (4) | C40—H40b | 0.96 |
C23—C24 | 1.366 (5) | C40—H40c | 0.96 |
C24—C25 | 1.384 (5) | C38'—H38c | 0.97 |
C25—C26 | 1.366 (4) | C38'—H38d | 0.97 |
C26—C27 | 1.411 (4) | C39'—H39c | 0.97 |
C27—C28 | 1.445 (4) | C39'—H39d | 0.97 |
C28—C29 | 1.417 (4) | C40'—H40d | 0.96 |
C30—C31 | 1.475 (4) | C40'—H40e | 0.96 |
C31—C36 | 1.379 (4) | C40'—H40f | 0.96 |
O1—V1—O2 | 136.38 (8) | C38'—C39'—C40' | 108 (1) |
O1—V1—O3 | 82.56 (8) | C3—C2—H2 | 119.9 |
O1—V1—O4 | 87.17 (9) | C1—C2—H2 | 119.9 |
O1—V1—N1 | 82.30 (9) | C2—C3—H3 | 118.7 |
O1—V1—N3 | 131.90 (9) | C4—C3—H3 | 118.7 |
O2—V1—O3 | 86.62 (9) | C6—C5—H5 | 119.4 |
O2—V1—O4 | 126.63 (9) | C4—C5—H5 | 119.4 |
O2—V1—N1 | 74.24 (8) | C5—C6—H6 | 120.2 |
O2—V1—N3 | 87.80 (8) | C7—C6—H6 | 120.2 |
O3—V1—O4 | 137.24 (9) | C8—C7—H7 | 119.5 |
O3—V1—N1 | 132.15 (9) | C6—C7—H7 | 119.5 |
O3—V1—N3 | 82.57 (9) | C7—C8—H8 | 119.4 |
O4—V1—N1 | 86.78 (9) | C9—C8—H8 | 119.4 |
O4—V1—N3 | 73.94 (8) | N1—C11—H11 | 118.0 |
N1—V1—N3 | 138.06 (9) | C10—C11—H11 | 118.0 |
C1—O1—V1 | 128.2 (2) | C15—C14—H14 | 119.7 |
C12—O2—V1 | 118.9 (2) | C13—C14—H14 | 119.7 |
C19—O3—V1 | 129.4 (2) | C14—C15—H15 | 120.1 |
C30—O4—V1 | 119.0 (2) | C16—C15—H15 | 120.1 |
C11—N1—N2 | 115.3 (2) | C17—C16—H16 | 120.1 |
C11—N1—V1 | 126.66 (18) | C15—C16—H16 | 120.1 |
N2—N1—V1 | 118.03 (16) | C16—C17—H17 | 119.6 |
C12—N2—N1 | 107.5 (2) | C18—C17—H17 | 119.6 |
C29—N3—N4 | 114.9 (2) | C17—C18—H18 | 119.9 |
C29—N3—V1 | 127.94 (17) | C13—C18—H18 | 119.9 |
N4—N3—V1 | 117.12 (16) | C21—C20—H20 | 119.8 |
C30—N4—N3 | 107.7 (2) | C19—C20—H20 | 119.8 |
O1—C1—C10 | 122.5 (2) | C20—C21—H21 | 118.9 |
O1—C1—C2 | 117.7 (2) | C22—C21—H21 | 118.9 |
C10—C1—C2 | 119.7 (2) | C24—C23—H23 | 119.3 |
C3—C2—C1 | 120.1 (3) | C22—C23—H23 | 119.3 |
C2—C3—C4 | 122.5 (3) | C23—C24—H24 | 120.4 |
C5—C4—C3 | 121.3 (3) | C25—C24—H24 | 120.4 |
C5—C4—C9 | 119.7 (3) | C26—C25—H25 | 119.3 |
C3—C4—C9 | 119.0 (3) | C24—C25—H25 | 119.3 |
C6—C5—C4 | 121.1 (3) | C25—C26—H26 | 119.4 |
C5—C6—C7 | 119.6 (3) | C27—C26—H26 | 119.4 |
C8—C7—C6 | 121.0 (3) | N3—C29—H29 | 117.7 |
C7—C8—C9 | 121.2 (3) | C28—C29—H29 | 117.7 |
C8—C9—C4 | 117.5 (3) | C31—C32—H32 | 120.2 |
C8—C9—C10 | 123.5 (3) | C33—C32—H32 | 120.2 |
C4—C9—C10 | 119.0 (2) | C34—C33—H33 | 119.5 |
C11—C10—C1 | 119.6 (2) | C32—C33—H33 | 119.5 |
C11—C10—C9 | 120.4 (2) | C35—C34—H34 | 120.4 |
C1—C10—C9 | 119.6 (2) | C33—C34—H34 | 120.4 |
N1—C11—C10 | 124.0 (2) | C34—C35—H35 | 119.6 |
N2—C12—O2 | 120.6 (2) | C36—C35—H35 | 119.6 |
N2—C12—C13 | 120.9 (2) | C31—C36—H36 | 120.1 |
O2—C12—C13 | 118.5 (2) | C35—C36—H36 | 120.1 |
C18—C13—C14 | 118.7 (3) | Cl1—C37—H37a | 109.3 |
C18—C13—C12 | 120.3 (3) | Cl2—C37—H37a | 109.3 |
C14—C13—C12 | 120.9 (3) | Cl1—C37—H37b | 109.3 |
C15—C14—C13 | 120.6 (3) | Cl2—C37—H37b | 109.3 |
C14—C15—C16 | 119.8 (4) | H37a—C37—H37b | 108.0 |
C17—C16—C15 | 119.8 (3) | Cl1—C37'—H37c | 110.3 |
C16—C17—C18 | 120.8 (4) | Cl2—C37'—H37c | 110.3 |
C17—C18—C13 | 120.2 (3) | Cl1—C37'—H37d | 110.3 |
O3—C19—C28 | 122.7 (2) | Cl2—C37'—H37d | 110.3 |
O3—C19—C20 | 117.2 (2) | H37c—C37'—H37d | 108.6 |
C28—C19—C20 | 119.9 (2) | C39—C38—H38a | 109.4 |
C21—C20—C19 | 120.4 (3) | C38i—C38—H38a | 109.4 |
C20—C21—C22 | 122.1 (3) | C39—C38—H38b | 109.4 |
C23—C22—C21 | 121.4 (3) | C38i—C38—H38b | 109.4 |
C23—C22—C27 | 119.5 (3) | H38a—C38—H38b | 108.0 |
C21—C22—C27 | 119.1 (3) | C40—C39—H39a | 108.1 |
C24—C23—C22 | 121.4 (3) | C38—C39—H39a | 108.1 |
C23—C24—C25 | 119.2 (3) | C40—C39—H39b | 108.1 |
C26—C25—C24 | 121.3 (3) | C38—C39—H39b | 108.1 |
C25—C26—C27 | 121.2 (3) | H39a—C39—H39b | 107.3 |
C26—C27—C22 | 117.4 (2) | C39—C40—H40a | 109.5 |
C26—C27—C28 | 123.6 (2) | C39—C40—H40b | 109.5 |
C22—C27—C28 | 119.0 (2) | H40a—C40—H40b | 109.5 |
C19—C28—C29 | 119.3 (2) | C39—C40—H40c | 109.5 |
C19—C28—C27 | 119.4 (2) | H40a—C40—H40c | 109.5 |
C29—C28—C27 | 120.9 (2) | H40b—C40—H40c | 109.5 |
N3—C29—C28 | 124.7 (2) | C39'—C38'—H38c | 109.0 |
N4—C30—O4 | 120.7 (2) | C38'i—C38'—H38c | 109.0 |
N4—C30—C31 | 121.2 (2) | C39'—C38'—H38d | 109.0 |
O4—C30—C31 | 118.1 (2) | C38'i—C38'—H38d | 109.0 |
C36—C31—C32 | 119.4 (3) | H38c—C38'—H38d | 107.8 |
C36—C31—C30 | 120.1 (2) | C38'—C39'—H39c | 110.2 |
C32—C31—C30 | 120.6 (3) | C40'—C39'—H39c | 110.2 |
C31—C32—C33 | 119.7 (3) | C38'—C39'—H39d | 110.2 |
C34—C33—C32 | 121.0 (3) | C40'—C39'—H39d | 110.2 |
C35—C34—C33 | 119.3 (3) | H39c—C39'—H39d | 108.5 |
C34—C35—C36 | 120.8 (3) | C39'—C40'—H40d | 109.5 |
C31—C36—C35 | 119.9 (3) | C39'—C40'—H40e | 109.5 |
Cl1—C37—Cl2 | 111.6 (2) | H40d—C40'—H40e | 109.5 |
Cl1—C37'—Cl2 | 107.0 (3) | C39'—C40'—H40f | 109.5 |
C39—C38—C38i | 111 (1) | H40d—C40'—H40f | 109.5 |
C40—C39—C38 | 116.6 (9) | H40e—C40'—H40f | 109.5 |
C39'—C38'—C38'i | 113 (2) | ||
O3—V1—O1—C1 | −179.0 (2) | V1—N1—C11—C10 | −9.6 (4) |
O4—V1—O1—C1 | 42.6 (2) | C1—C10—C11—N1 | −15.6 (4) |
O2—V1—O1—C1 | −101.9 (2) | C9—C10—C11—N1 | 171.5 (2) |
N1—V1—O1—C1 | −44.6 (2) | N1—N2—C12—O2 | −0.7 (3) |
N3—V1—O1—C1 | 108.0 (2) | N1—N2—C12—C13 | 177.9 (2) |
O1—V1—O2—C12 | 67.0 (2) | V1—O2—C12—N2 | −5.8 (3) |
O3—V1—O2—C12 | 142.49 (19) | V1—O2—C12—C13 | 175.57 (17) |
O4—V1—O2—C12 | −66.7 (2) | N2—C12—C13—C18 | 178.2 (3) |
N1—V1—O2—C12 | 6.84 (18) | O2—C12—C13—C18 | −3.1 (4) |
N3—V1—O2—C12 | −134.82 (19) | N2—C12—C13—C14 | −1.5 (4) |
O1—V1—O3—C19 | −175.2 (2) | O2—C12—C13—C14 | 177.1 (3) |
O4—V1—O3—C19 | −97.5 (2) | C18—C13—C14—C15 | 1.0 (5) |
O2—V1—O3—C19 | 47.2 (2) | C12—C13—C14—C15 | −179.2 (3) |
N1—V1—O3—C19 | 112.3 (2) | C13—C14—C15—C16 | 0.2 (6) |
N3—V1—O3—C19 | −41.0 (2) | C14—C15—C16—C17 | −1.4 (7) |
O1—V1—O4—C30 | 146.23 (19) | C15—C16—C17—C18 | 1.4 (7) |
O3—V1—O4—C30 | 70.4 (2) | C16—C17—C18—C13 | −0.2 (6) |
O2—V1—O4—C30 | −63.7 (2) | C14—C13—C18—C17 | −1.1 (5) |
N1—V1—O4—C30 | −131.33 (19) | C12—C13—C18—C17 | 179.2 (3) |
N3—V1—O4—C30 | 10.99 (18) | V1—O3—C19—C28 | 38.1 (4) |
O1—V1—N1—C11 | 31.3 (2) | V1—O3—C19—C20 | −146.9 (2) |
O3—V1—N1—C11 | 103.9 (2) | O3—C19—C20—C21 | −171.7 (3) |
O4—V1—N1—C11 | −56.3 (2) | C28—C19—C20—C21 | 3.5 (4) |
O2—V1—N1—C11 | 174.1 (2) | C19—C20—C21—C22 | −0.8 (5) |
N3—V1—N1—C11 | −117.8 (2) | C20—C21—C22—C23 | 177.6 (3) |
O1—V1—N1—N2 | −150.26 (19) | C20—C21—C22—C27 | −1.4 (5) |
O3—V1—N1—N2 | −77.6 (2) | C21—C22—C23—C24 | 179.3 (3) |
O4—V1—N1—N2 | 122.16 (19) | C27—C22—C23—C24 | −1.8 (5) |
O2—V1—N1—N2 | −7.39 (17) | C22—C23—C24—C25 | 0.7 (5) |
N3—V1—N1—N2 | 60.7 (2) | C23—C24—C25—C26 | 0.2 (5) |
C11—N1—N2—C12 | −174.8 (2) | C24—C25—C26—C27 | 0.0 (5) |
V1—N1—N2—C12 | 6.5 (3) | C25—C26—C27—C22 | −1.0 (4) |
O1—V1—N3—C29 | 97.5 (2) | C25—C26—C27—C28 | 178.9 (3) |
O3—V1—N3—C29 | 24.5 (2) | C23—C22—C27—C26 | 1.9 (4) |
O4—V1—N3—C29 | 168.4 (2) | C21—C22—C27—C26 | −179.1 (3) |
O2—V1—N3—C29 | −62.4 (2) | C23—C22—C27—C28 | −178.1 (3) |
N1—V1—N3—C29 | −125.7 (2) | C21—C22—C27—C28 | 0.9 (4) |
O1—V1—N3—N4 | −81.3 (2) | O3—C19—C28—C29 | −2.5 (4) |
O3—V1—N3—N4 | −154.30 (19) | C20—C19—C28—C29 | −177.4 (2) |
O4—V1—N3—N4 | −10.40 (17) | O3—C19—C28—C27 | 171.0 (2) |
O2—V1—N3—N4 | 118.83 (18) | C20—C19—C28—C27 | −3.9 (4) |
N1—V1—N3—N4 | 55.5 (2) | C26—C27—C28—C19 | −178.3 (3) |
C29—N3—N4—C30 | −171.0 (2) | C22—C27—C28—C19 | 1.7 (4) |
V1—N3—N4—C30 | 7.9 (3) | C26—C27—C28—C29 | −4.9 (4) |
V1—O1—C1—C10 | 35.8 (3) | C22—C27—C28—C29 | 175.1 (2) |
V1—O1—C1—C2 | −147.89 (19) | N4—N3—C29—C28 | 173.6 (2) |
O1—C1—C2—C3 | −177.8 (2) | V1—N3—C29—C28 | −5.2 (4) |
C10—C1—C2—C3 | −1.4 (4) | C19—C28—C29—N3 | −12.3 (4) |
C1—C2—C3—C4 | 0.4 (4) | C27—C28—C29—N3 | 174.3 (2) |
C2—C3—C4—C5 | 179.6 (3) | N3—N4—C30—O4 | 1.3 (3) |
C2—C3—C4—C9 | 1.1 (4) | N3—N4—C30—C31 | −179.9 (2) |
C3—C4—C5—C6 | −178.3 (3) | V1—O4—C30—N4 | −10.9 (3) |
C9—C4—C5—C6 | 0.2 (4) | V1—O4—C30—C31 | 170.28 (18) |
C4—C5—C6—C7 | 0.6 (5) | N4—C30—C31—C36 | 180.0 (3) |
C5—C6—C7—C8 | −1.3 (5) | O4—C30—C31—C36 | −1.3 (4) |
C6—C7—C8—C9 | 1.3 (5) | N4—C30—C31—C32 | 1.1 (4) |
C7—C8—C9—C4 | −0.4 (4) | O4—C30—C31—C32 | 179.9 (3) |
C7—C8—C9—C10 | 179.3 (3) | C36—C31—C32—C33 | 1.6 (5) |
C5—C4—C9—C8 | −0.3 (4) | C30—C31—C32—C33 | −179.5 (3) |
C3—C4—C9—C8 | 178.2 (3) | C31—C32—C33—C34 | −0.9 (6) |
C5—C4—C9—C10 | 179.9 (2) | C32—C33—C34—C35 | 0.1 (7) |
C3—C4—C9—C10 | −1.5 (4) | C33—C34—C35—C36 | 0.1 (6) |
O1—C1—C10—C11 | 4.2 (4) | C32—C31—C36—C35 | −1.4 (5) |
C2—C1—C10—C11 | −172.1 (2) | C30—C31—C36—C35 | 179.7 (3) |
O1—C1—C10—C9 | 177.1 (2) | C34—C35—C36—C31 | 0.6 (6) |
C2—C1—C10—C9 | 0.9 (4) | C37'—Cl1—C37—Cl2 | −68.7 (7) |
C8—C9—C10—C11 | −6.3 (4) | C37'—Cl2—C37—Cl1 | 68.9 (7) |
C4—C9—C10—C11 | 173.5 (2) | C37—Cl1—C37'—Cl2 | 62.0 (6) |
C8—C9—C10—C1 | −179.2 (3) | C37—Cl2—C37'—Cl1 | −61.5 (6) |
C4—C9—C10—C1 | 0.6 (4) | C38i—C38—C39—C40 | −166.0 (17) |
N2—N1—C11—C10 | 171.8 (2) | C38'i—C38'—C39'—C40' | −98 (5) |
Symmetry code: (i) −x+1, −y+1, −z+2. |