The title compound consists of discrete complexes with a square-pyramidal NiN
5 coordination polyhedron for the metal ions. The complexes are linked by C—H

F hydrogen bonds into chains propagating along [001].
Supporting information
CCDC reference: 1951945
Key indicators
- Single-crystal X-ray study
- T = 170 K
- Mean
(C-C) = 0.007 Å
- R factor = 0.043
- wR factor = 0.099
- Data-to-parameter ratio = 16.8
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT334_ALERT_2_C Small Aver. Benzene C-C Dist C53 -C58 1.37 Ang.
PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds ............... 0.00654 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H33B ..F8 . 2.63 Ang.
PLAT911_ALERT_3_C Missing FCF Refl Between Thmin & STh/L= 0.600 2 Report
PLAT978_ALERT_2_C Number C-C Bonds with Positive Residual Density. 0 Info
Alert level G
PLAT012_ALERT_1_G N.O.K. _shelx_res_checksum Found in CIF ...... Please Check
PLAT432_ALERT_2_G Short Inter X...Y Contact F3 ..C62 2.97 Ang.
-1/2+x,1/2-y,1-z = 4_456 Check
PLAT605_ALERT_4_G Largest Solvent Accessible VOID in the Structure 332 A 3
PLAT794_ALERT_5_G Tentative Bond Valency for Ni1 (II) . 1.95 Info
PLAT913_ALERT_3_G Missing # of Very Strong Reflections in FCF .... 2 Note
0 ALERT level A = Most likely a serious problem - resolve or explain
0 ALERT level B = A potentially serious problem, consider carefully
5 ALERT level C = Check. Ensure it is not caused by an omission or oversight
5 ALERT level G = General information/check it is not something unexpected
1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
3 ALERT type 2 Indicator that the structure model may be wrong or deficient
3 ALERT type 3 Indicator that the structure quality may be low
2 ALERT type 4 Improvement, methodology, query or suggestion
1 ALERT type 5 Informative message, check
Data collection: X-AREA (Stoe, 2008); cell refinement: X-AREA (Stoe, 2008); data reduction: X-AREA (Stoe, 2008); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: XP (Sheldrick, 2008) and Diamond (Brandenburg, 2014); software used to prepare material for publication: publCIF (Westrip, 2010).
(15,20-Bis(2,3,4,5,6-pentafluorophenyl)-5,10-{(4-methylpyridine-3,5-diyl)\
bis[(sulfanediylmethylene)[1,1'-biphenyl]-4',2-diyl]}porphyrinato)nickel(II)
dichloromethane solvate
top
Crystal data top
[Ni(C64H33F10N5S2)][+solvent] | Dx = 1.384 Mg m−3 |
Mr = 1184.78 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 44396 reflections |
a = 12.6269 (2) Å | θ = 1.4–27.0° |
b = 18.0525 (3) Å | µ = 0.49 mm−1 |
c = 24.9524 (6) Å | T = 170 K |
V = 5687.83 (19) Å3 | Block, red |
Z = 4 | 0.15 × 0.10 × 0.05 mm |
F(000) = 2408 | |
Data collection top
Stoe IPDS-2 diffractometer | 10468 reflections with I > 2σ(I) |
ω scans | Rint = 0.055 |
Absorption correction: numerical (X-Red and X-Shape; Stoe, 2008) | θmax = 27.0°, θmin = 1.4° |
Tmin = 0.810, Tmax = 0.965 | h = −16→14 |
44401 measured reflections | k = −23→20 |
12417 independent reflections | l = −31→31 |
Refinement top
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0479P)2 + 0.9016P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.099 | (Δ/σ)max < 0.001 |
S = 1.04 | Δρmax = 0.34 e Å−3 |
12417 reflections | Δρmin = −0.39 e Å−3 |
740 parameters | Absolute structure: Flack x determined using 4043 quotients
[(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.004 (7) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Ni1 | 0.36866 (4) | 0.61346 (3) | 0.57341 (2) | 0.03235 (11) | |
N1 | 0.3385 (2) | 0.71635 (17) | 0.60371 (11) | 0.0329 (7) | |
N2 | 0.2384 (3) | 0.57504 (17) | 0.61227 (12) | 0.0340 (7) | |
N3 | 0.3742 (3) | 0.51813 (17) | 0.52990 (11) | 0.0374 (7) | |
N4 | 0.4729 (3) | 0.66068 (18) | 0.52138 (11) | 0.0337 (7) | |
C1 | 0.3978 (3) | 0.7789 (2) | 0.59612 (14) | 0.0361 (8) | |
C2 | 0.3622 (4) | 0.8368 (2) | 0.63062 (15) | 0.0411 (8) | |
H2 | 0.3916 | 0.8851 | 0.6336 | 0.049* | |
C3 | 0.2787 (3) | 0.8098 (2) | 0.65832 (15) | 0.0385 (8) | |
H3 | 0.2376 | 0.8358 | 0.6841 | 0.046* | |
C4 | 0.2636 (3) | 0.7342 (2) | 0.64145 (14) | 0.0335 (8) | |
C5 | 0.1883 (3) | 0.6867 (2) | 0.66275 (14) | 0.0348 (8) | |
C6 | 0.1780 (3) | 0.6117 (2) | 0.64944 (13) | 0.0342 (7) | |
C7 | 0.1072 (3) | 0.5608 (2) | 0.67541 (15) | 0.0387 (9) | |
H7 | 0.0574 | 0.5724 | 0.7027 | 0.046* | |
C8 | 0.1249 (4) | 0.4939 (2) | 0.65372 (15) | 0.0429 (9) | |
H8 | 0.0898 | 0.4491 | 0.6629 | 0.052* | |
C9 | 0.2067 (3) | 0.5023 (2) | 0.61405 (15) | 0.0378 (8) | |
C10 | 0.2491 (3) | 0.4457 (2) | 0.58317 (14) | 0.0382 (8) | |
C11 | 0.3253 (3) | 0.4528 (2) | 0.54297 (15) | 0.0388 (8) | |
C12 | 0.3605 (4) | 0.3948 (2) | 0.50759 (17) | 0.0496 (10) | |
H12 | 0.3392 | 0.3444 | 0.5084 | 0.060* | |
C13 | 0.4297 (4) | 0.4262 (3) | 0.47302 (17) | 0.0497 (10) | |
H13 | 0.4650 | 0.4019 | 0.4443 | 0.060* | |
C14 | 0.4400 (3) | 0.5026 (2) | 0.48752 (15) | 0.0385 (8) | |
C15 | 0.5083 (3) | 0.5531 (2) | 0.46350 (14) | 0.0382 (8) | |
C16 | 0.5222 (3) | 0.6268 (2) | 0.47900 (13) | 0.0342 (8) | |
C17 | 0.5939 (3) | 0.6784 (2) | 0.45336 (16) | 0.0423 (9) | |
H17 | 0.6376 | 0.6687 | 0.4232 | 0.051* | |
C18 | 0.5869 (3) | 0.7423 (2) | 0.48022 (15) | 0.0417 (9) | |
H18 | 0.6247 | 0.7865 | 0.4726 | 0.050* | |
C19 | 0.5114 (3) | 0.7316 (2) | 0.52279 (14) | 0.0359 (8) | |
C20 | 0.4805 (3) | 0.7864 (2) | 0.55899 (14) | 0.0368 (8) | |
C21 | 0.1169 (3) | 0.7200 (2) | 0.70420 (15) | 0.0385 (8) | |
C22 | 0.1413 (4) | 0.7145 (3) | 0.75868 (16) | 0.0480 (10) | |
C23 | 0.0784 (5) | 0.7530 (3) | 0.7952 (2) | 0.0701 (16) | |
H23 | 0.0942 | 0.7501 | 0.8324 | 0.084* | |
C24 | −0.0060 (5) | 0.7952 (3) | 0.7784 (2) | 0.0754 (17) | |
H24 | −0.0465 | 0.8221 | 0.8039 | 0.090* | |
C25 | −0.0319 (5) | 0.7984 (3) | 0.7248 (2) | 0.0630 (14) | |
H25 | −0.0918 | 0.8261 | 0.7134 | 0.076* | |
C26 | 0.0293 (4) | 0.7613 (3) | 0.68774 (18) | 0.0481 (10) | |
H26 | 0.0118 | 0.7639 | 0.6508 | 0.058* | |
C27 | 0.2296 (4) | 0.6651 (3) | 0.77658 (16) | 0.0495 (11) | |
C28 | 0.3349 (4) | 0.6799 (3) | 0.76606 (18) | 0.0562 (12) | |
H28 | 0.3544 | 0.7260 | 0.7506 | 0.067* | |
C29 | 0.4124 (4) | 0.6277 (3) | 0.77794 (18) | 0.0589 (13) | |
H29 | 0.4847 | 0.6393 | 0.7716 | 0.071* | |
C30 | 0.3863 (4) | 0.5589 (3) | 0.79893 (17) | 0.0572 (12) | |
C31 | 0.2806 (4) | 0.5464 (3) | 0.8117 (2) | 0.0631 (14) | |
H31 | 0.2611 | 0.5011 | 0.8284 | 0.076* | |
C32 | 0.2040 (4) | 0.5979 (3) | 0.80093 (18) | 0.0584 (13) | |
H32 | 0.1324 | 0.5878 | 0.8101 | 0.070* | |
C33 | 0.4666 (4) | 0.4992 (4) | 0.80592 (18) | 0.0669 (15) | |
H33A | 0.4555 | 0.4748 | 0.8410 | 0.080* | |
H33B | 0.5382 | 0.5215 | 0.8061 | 0.080* | |
S1 | 0.45960 (12) | 0.42922 (8) | 0.75272 (5) | 0.0652 (4) | |
C34 | 0.5137 (4) | 0.4798 (3) | 0.69782 (17) | 0.0488 (10) | |
C35 | 0.4473 (4) | 0.5274 (2) | 0.67001 (16) | 0.0442 (10) | |
H35 | 0.3763 | 0.5329 | 0.6820 | 0.053* | |
N5 | 0.4788 (3) | 0.5663 (2) | 0.62680 (12) | 0.0397 (7) | |
C36 | 0.5793 (3) | 0.5587 (3) | 0.61168 (17) | 0.0449 (9) | |
H36 | 0.6028 | 0.5858 | 0.5813 | 0.054* | |
C37 | 0.6515 (4) | 0.5137 (3) | 0.63743 (17) | 0.0516 (11) | |
C38 | 0.6190 (4) | 0.4710 (3) | 0.68145 (17) | 0.0494 (10) | |
C39 | 0.6924 (5) | 0.4168 (3) | 0.7083 (2) | 0.0659 (14) | |
H39A | 0.6722 | 0.4113 | 0.7460 | 0.099* | |
H39B | 0.7653 | 0.4351 | 0.7060 | 0.099* | |
H39C | 0.6873 | 0.3687 | 0.6903 | 0.099* | |
S2 | 0.78309 (11) | 0.51140 (10) | 0.61283 (6) | 0.0702 (4) | |
C40 | 0.8384 (4) | 0.5904 (4) | 0.6494 (2) | 0.080 (2) | |
H40A | 0.8259 | 0.5830 | 0.6882 | 0.095* | |
H40B | 0.9159 | 0.5917 | 0.6436 | 0.095* | |
C41 | 0.7924 (4) | 0.6637 (4) | 0.63313 (19) | 0.0633 (14) | |
C42 | 0.7113 (4) | 0.6972 (4) | 0.66102 (18) | 0.0649 (15) | |
H42 | 0.6871 | 0.6754 | 0.6935 | 0.078* | |
C43 | 0.6643 (4) | 0.7615 (3) | 0.64298 (18) | 0.0607 (13) | |
H43 | 0.6077 | 0.7828 | 0.6627 | 0.073* | |
C44 | 0.6989 (4) | 0.7953 (3) | 0.59624 (17) | 0.0518 (11) | |
C45 | 0.7836 (4) | 0.7635 (3) | 0.5695 (2) | 0.0630 (13) | |
H45 | 0.8105 | 0.7867 | 0.5382 | 0.076* | |
C46 | 0.8301 (4) | 0.6984 (4) | 0.5873 (2) | 0.0658 (14) | |
H46 | 0.8878 | 0.6775 | 0.5681 | 0.079* | |
C47 | 0.6447 (4) | 0.8620 (3) | 0.57452 (17) | 0.0516 (10) | |
C48 | 0.5386 (4) | 0.8582 (2) | 0.55788 (16) | 0.0442 (10) | |
C49 | 0.4884 (5) | 0.9215 (3) | 0.53857 (18) | 0.0548 (12) | |
H49 | 0.4171 | 0.9190 | 0.5264 | 0.066* | |
C50 | 0.5429 (6) | 0.9883 (3) | 0.5372 (2) | 0.0734 (17) | |
H50 | 0.5077 | 1.0321 | 0.5259 | 0.088* | |
C51 | 0.6486 (6) | 0.9911 (3) | 0.5521 (2) | 0.0768 (19) | |
H51 | 0.6863 | 1.0366 | 0.5497 | 0.092* | |
C52 | 0.6982 (5) | 0.9296 (3) | 0.5701 (2) | 0.0661 (15) | |
H52 | 0.7707 | 0.9323 | 0.5800 | 0.079* | |
C53 | 0.2096 (4) | 0.3686 (2) | 0.59367 (16) | 0.0428 (9) | |
C54 | 0.1119 (4) | 0.3441 (2) | 0.57611 (18) | 0.0492 (10) | |
C55 | 0.0757 (4) | 0.2733 (3) | 0.58575 (19) | 0.0549 (12) | |
C56 | 0.1364 (5) | 0.2256 (2) | 0.6139 (2) | 0.0609 (12) | |
C57 | 0.2319 (5) | 0.2470 (3) | 0.6320 (2) | 0.0666 (14) | |
C58 | 0.2688 (4) | 0.3177 (3) | 0.6224 (2) | 0.0569 (12) | |
F1 | 0.0481 (3) | 0.38982 (19) | 0.54925 (13) | 0.0742 (9) | |
F2 | −0.0200 (3) | 0.25128 (18) | 0.56817 (14) | 0.0788 (9) | |
F3 | 0.0995 (3) | 0.15736 (17) | 0.62517 (16) | 0.0862 (11) | |
F4 | 0.2921 (4) | 0.2008 (2) | 0.6617 (2) | 0.1099 (15) | |
F5 | 0.3640 (3) | 0.33798 (18) | 0.64045 (15) | 0.0827 (10) | |
C59 | 0.5742 (3) | 0.5266 (2) | 0.41772 (15) | 0.0400 (9) | |
C60 | 0.6774 (3) | 0.5037 (3) | 0.42437 (17) | 0.0475 (9) | |
C61 | 0.7405 (4) | 0.4800 (3) | 0.38280 (17) | 0.0472 (10) | |
C62 | 0.6994 (4) | 0.4791 (2) | 0.33204 (16) | 0.0459 (10) | |
C63 | 0.5979 (4) | 0.5029 (3) | 0.32304 (15) | 0.0456 (10) | |
C64 | 0.5368 (3) | 0.5260 (3) | 0.36550 (16) | 0.0437 (9) | |
F6 | 0.7198 (2) | 0.5046 (2) | 0.47407 (10) | 0.0686 (8) | |
F7 | 0.8392 (2) | 0.4563 (2) | 0.39158 (12) | 0.0704 (9) | |
F8 | 0.7586 (2) | 0.45350 (17) | 0.29130 (10) | 0.0613 (7) | |
F9 | 0.5582 (3) | 0.50154 (19) | 0.27319 (10) | 0.0686 (8) | |
F10 | 0.4375 (2) | 0.54870 (18) | 0.35559 (10) | 0.0598 (7) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Ni1 | 0.0320 (2) | 0.0340 (2) | 0.03107 (19) | −0.0007 (2) | 0.00063 (19) | 0.00143 (18) |
N1 | 0.0336 (17) | 0.0328 (16) | 0.0324 (15) | −0.0034 (13) | 0.0006 (12) | 0.0022 (12) |
N2 | 0.0353 (17) | 0.0312 (16) | 0.0354 (14) | 0.0007 (14) | −0.0009 (13) | 0.0008 (12) |
N3 | 0.0395 (17) | 0.0364 (16) | 0.0364 (14) | −0.0033 (16) | 0.0048 (14) | 0.0013 (12) |
N4 | 0.0329 (16) | 0.0352 (17) | 0.0330 (14) | −0.0004 (14) | 0.0005 (12) | 0.0007 (12) |
C1 | 0.037 (2) | 0.0354 (19) | 0.0363 (16) | −0.0058 (16) | 0.0008 (14) | 0.0015 (15) |
C2 | 0.042 (2) | 0.037 (2) | 0.0441 (19) | −0.0073 (19) | −0.0005 (18) | −0.0016 (15) |
C3 | 0.039 (2) | 0.038 (2) | 0.0377 (18) | −0.0006 (18) | 0.0012 (16) | −0.0038 (15) |
C4 | 0.0333 (19) | 0.0346 (19) | 0.0324 (16) | 0.0029 (16) | −0.0022 (14) | 0.0011 (14) |
C5 | 0.033 (2) | 0.038 (2) | 0.0335 (17) | −0.0002 (16) | −0.0038 (14) | 0.0002 (15) |
C6 | 0.0290 (16) | 0.0396 (19) | 0.0339 (16) | 0.0009 (18) | 0.0006 (13) | 0.0016 (16) |
C7 | 0.037 (2) | 0.042 (2) | 0.0370 (17) | −0.0016 (17) | 0.0042 (15) | 0.0023 (16) |
C8 | 0.044 (2) | 0.037 (2) | 0.0482 (19) | −0.006 (2) | 0.0050 (18) | 0.0063 (16) |
C9 | 0.038 (2) | 0.035 (2) | 0.0404 (18) | −0.0072 (17) | −0.0003 (16) | 0.0038 (16) |
C10 | 0.041 (2) | 0.0336 (19) | 0.0398 (19) | −0.0007 (17) | 0.0039 (16) | 0.0031 (15) |
C11 | 0.043 (2) | 0.0299 (19) | 0.0438 (19) | −0.0038 (17) | 0.0031 (16) | −0.0017 (16) |
C12 | 0.059 (3) | 0.036 (2) | 0.054 (2) | −0.005 (2) | 0.011 (2) | −0.0063 (18) |
C13 | 0.057 (3) | 0.045 (2) | 0.047 (2) | −0.001 (2) | 0.011 (2) | −0.0063 (19) |
C14 | 0.040 (2) | 0.037 (2) | 0.0382 (18) | 0.0011 (18) | 0.0052 (15) | −0.0037 (16) |
C15 | 0.037 (2) | 0.044 (2) | 0.0340 (17) | 0.0013 (18) | 0.0035 (15) | −0.0002 (16) |
C16 | 0.0361 (19) | 0.039 (2) | 0.0275 (15) | −0.0013 (16) | 0.0032 (13) | 0.0017 (14) |
C17 | 0.042 (2) | 0.048 (2) | 0.0376 (19) | −0.0022 (19) | 0.0075 (16) | 0.0015 (17) |
C18 | 0.040 (2) | 0.044 (2) | 0.0409 (19) | −0.0069 (18) | 0.0082 (16) | 0.0017 (17) |
C19 | 0.036 (2) | 0.037 (2) | 0.0341 (17) | −0.0068 (17) | 0.0034 (15) | 0.0038 (15) |
C20 | 0.036 (2) | 0.036 (2) | 0.0382 (18) | −0.0024 (16) | 0.0012 (15) | 0.0018 (15) |
C21 | 0.036 (2) | 0.036 (2) | 0.0427 (18) | −0.0001 (17) | 0.0065 (16) | −0.0001 (15) |
C22 | 0.051 (3) | 0.052 (2) | 0.0406 (19) | 0.000 (2) | 0.0085 (19) | −0.0008 (17) |
C23 | 0.094 (4) | 0.073 (4) | 0.043 (2) | 0.013 (3) | 0.024 (3) | −0.003 (2) |
C24 | 0.093 (4) | 0.070 (4) | 0.064 (3) | 0.030 (3) | 0.031 (3) | −0.001 (3) |
C25 | 0.063 (3) | 0.054 (3) | 0.073 (3) | 0.020 (3) | 0.032 (3) | 0.011 (2) |
C26 | 0.043 (2) | 0.049 (3) | 0.052 (2) | 0.008 (2) | 0.0078 (19) | 0.0059 (19) |
C27 | 0.051 (3) | 0.062 (3) | 0.0351 (19) | 0.000 (2) | 0.0004 (18) | 0.0011 (18) |
C28 | 0.051 (3) | 0.069 (3) | 0.049 (2) | −0.007 (2) | 0.000 (2) | 0.004 (2) |
C29 | 0.047 (3) | 0.085 (4) | 0.045 (2) | −0.006 (3) | −0.0011 (19) | 0.006 (2) |
C30 | 0.048 (3) | 0.084 (4) | 0.039 (2) | 0.004 (3) | −0.0033 (19) | 0.011 (2) |
C31 | 0.052 (3) | 0.083 (4) | 0.054 (3) | 0.002 (3) | 0.001 (2) | 0.027 (3) |
C32 | 0.045 (2) | 0.080 (4) | 0.050 (2) | −0.003 (3) | 0.0022 (19) | 0.020 (2) |
C33 | 0.053 (3) | 0.106 (4) | 0.042 (2) | 0.014 (3) | −0.003 (2) | 0.021 (3) |
S1 | 0.0664 (8) | 0.0700 (9) | 0.0591 (7) | 0.0039 (7) | −0.0009 (6) | 0.0279 (6) |
C34 | 0.051 (3) | 0.052 (3) | 0.043 (2) | 0.004 (2) | −0.0077 (18) | 0.0050 (18) |
C35 | 0.043 (2) | 0.049 (2) | 0.0407 (19) | 0.002 (2) | −0.0030 (17) | 0.0088 (17) |
N5 | 0.0358 (18) | 0.048 (2) | 0.0354 (15) | 0.0004 (15) | −0.0022 (13) | 0.0080 (14) |
C36 | 0.037 (2) | 0.054 (3) | 0.044 (2) | 0.006 (2) | −0.0011 (17) | 0.0080 (19) |
C37 | 0.045 (3) | 0.062 (3) | 0.048 (2) | 0.011 (2) | −0.0038 (18) | 0.004 (2) |
C38 | 0.047 (3) | 0.052 (3) | 0.049 (2) | 0.009 (2) | −0.0077 (19) | 0.0036 (18) |
C39 | 0.065 (3) | 0.064 (3) | 0.068 (3) | 0.018 (3) | −0.009 (3) | 0.015 (3) |
S2 | 0.0454 (7) | 0.0985 (11) | 0.0666 (7) | 0.0231 (7) | 0.0050 (6) | 0.0145 (7) |
C40 | 0.042 (3) | 0.130 (6) | 0.067 (3) | 0.006 (3) | −0.009 (2) | 0.023 (3) |
C41 | 0.039 (2) | 0.100 (4) | 0.051 (2) | −0.006 (3) | −0.009 (2) | 0.006 (3) |
C42 | 0.049 (3) | 0.104 (4) | 0.042 (2) | −0.012 (3) | −0.004 (2) | 0.008 (3) |
C43 | 0.051 (3) | 0.090 (4) | 0.041 (2) | −0.012 (3) | 0.0000 (19) | 0.001 (2) |
C44 | 0.041 (2) | 0.072 (3) | 0.043 (2) | −0.015 (2) | −0.0008 (18) | −0.005 (2) |
C45 | 0.046 (3) | 0.088 (4) | 0.055 (2) | −0.011 (3) | 0.009 (2) | 0.004 (3) |
C46 | 0.038 (2) | 0.099 (4) | 0.061 (3) | −0.010 (3) | 0.005 (2) | 0.005 (3) |
C47 | 0.052 (3) | 0.059 (3) | 0.0435 (19) | −0.020 (2) | 0.013 (2) | −0.005 (2) |
C48 | 0.047 (2) | 0.042 (2) | 0.043 (2) | −0.0123 (19) | 0.0121 (17) | −0.0017 (16) |
C49 | 0.069 (3) | 0.043 (2) | 0.052 (2) | −0.007 (2) | 0.012 (2) | 0.003 (2) |
C50 | 0.110 (5) | 0.043 (3) | 0.067 (3) | −0.013 (3) | 0.025 (3) | 0.001 (2) |
C51 | 0.106 (5) | 0.053 (3) | 0.071 (3) | −0.041 (4) | 0.031 (3) | −0.009 (3) |
C52 | 0.071 (3) | 0.074 (4) | 0.053 (2) | −0.038 (3) | 0.013 (3) | −0.016 (3) |
C53 | 0.047 (2) | 0.037 (2) | 0.0452 (19) | −0.0023 (18) | 0.0059 (18) | 0.0032 (16) |
C54 | 0.060 (3) | 0.042 (2) | 0.046 (2) | −0.010 (2) | −0.002 (2) | 0.0081 (19) |
C55 | 0.064 (3) | 0.044 (2) | 0.057 (3) | −0.018 (2) | 0.001 (2) | −0.002 (2) |
C56 | 0.074 (3) | 0.030 (2) | 0.079 (3) | −0.012 (2) | 0.008 (3) | 0.005 (2) |
C57 | 0.067 (3) | 0.038 (2) | 0.095 (4) | 0.007 (2) | −0.007 (3) | 0.021 (2) |
C58 | 0.048 (3) | 0.046 (3) | 0.077 (3) | 0.000 (2) | 0.000 (2) | 0.005 (2) |
F1 | 0.075 (2) | 0.0631 (18) | 0.0844 (19) | −0.0207 (18) | −0.0285 (16) | 0.0286 (16) |
F2 | 0.082 (2) | 0.0674 (19) | 0.087 (2) | −0.0361 (17) | −0.0184 (19) | 0.0069 (17) |
F3 | 0.104 (3) | 0.0368 (15) | 0.118 (3) | −0.0149 (17) | 0.003 (2) | 0.0147 (16) |
F4 | 0.097 (3) | 0.057 (2) | 0.176 (4) | 0.007 (2) | −0.026 (3) | 0.049 (2) |
F5 | 0.0599 (19) | 0.0634 (19) | 0.125 (3) | −0.0026 (18) | −0.026 (2) | 0.0207 (18) |
C59 | 0.039 (2) | 0.043 (2) | 0.038 (2) | −0.0021 (17) | 0.0040 (15) | −0.0020 (16) |
C60 | 0.043 (2) | 0.061 (3) | 0.0383 (18) | 0.001 (2) | −0.0013 (18) | −0.005 (2) |
C61 | 0.038 (2) | 0.052 (3) | 0.051 (2) | 0.004 (2) | 0.0082 (18) | −0.0058 (19) |
C62 | 0.051 (3) | 0.046 (2) | 0.041 (2) | −0.003 (2) | 0.0152 (18) | −0.0072 (17) |
C63 | 0.053 (3) | 0.050 (2) | 0.0338 (18) | −0.006 (2) | 0.0047 (16) | −0.0030 (17) |
C64 | 0.041 (2) | 0.050 (2) | 0.0411 (19) | −0.001 (2) | 0.0033 (17) | −0.0011 (17) |
F6 | 0.0516 (16) | 0.110 (3) | 0.0438 (13) | 0.0159 (18) | −0.0031 (12) | −0.0095 (15) |
F7 | 0.0442 (16) | 0.096 (2) | 0.0709 (17) | 0.0195 (16) | 0.0073 (13) | −0.0099 (16) |
F8 | 0.0660 (18) | 0.0676 (18) | 0.0502 (14) | 0.0031 (15) | 0.0220 (13) | −0.0118 (12) |
F9 | 0.0723 (19) | 0.096 (2) | 0.0375 (12) | −0.0010 (19) | −0.0001 (12) | −0.0108 (14) |
F10 | 0.0475 (15) | 0.084 (2) | 0.0476 (13) | 0.0108 (15) | −0.0008 (11) | −0.0029 (13) |
Geometric parameters (Å, º) top
Ni1—N2 | 2.031 (3) | C32—H32 | 0.9500 |
Ni1—N4 | 2.036 (3) | C33—S1 | 1.834 (6) |
Ni1—N3 | 2.036 (3) | C33—H33A | 0.9900 |
Ni1—N1 | 2.041 (3) | C33—H33B | 0.9900 |
Ni1—N5 | 2.106 (3) | S1—C34 | 1.782 (5) |
N1—C1 | 1.368 (5) | C34—C35 | 1.387 (6) |
N1—C4 | 1.373 (5) | C34—C38 | 1.401 (7) |
N2—C6 | 1.371 (5) | C35—N5 | 1.347 (5) |
N2—C9 | 1.373 (5) | C35—H35 | 0.9500 |
N3—C11 | 1.372 (5) | N5—C36 | 1.331 (5) |
N3—C14 | 1.374 (5) | C36—C37 | 1.379 (6) |
N4—C19 | 1.370 (5) | C36—H36 | 0.9500 |
N4—C16 | 1.371 (5) | C37—C38 | 1.403 (6) |
C1—C20 | 1.402 (5) | C37—S2 | 1.772 (5) |
C1—C2 | 1.427 (6) | C38—C39 | 1.505 (6) |
C2—C3 | 1.352 (6) | C39—H39A | 0.9800 |
C2—H2 | 0.9500 | C39—H39B | 0.9800 |
C3—C4 | 1.442 (5) | C39—H39C | 0.9800 |
C3—H3 | 0.9500 | S2—C40 | 1.832 (7) |
C4—C5 | 1.386 (5) | C40—C41 | 1.501 (9) |
C5—C6 | 1.400 (6) | C40—H40A | 0.9900 |
C5—C21 | 1.498 (5) | C40—H40B | 0.9900 |
C6—C7 | 1.435 (5) | C41—C42 | 1.379 (8) |
C7—C8 | 1.344 (6) | C41—C46 | 1.388 (7) |
C7—H7 | 0.9500 | C42—C43 | 1.379 (8) |
C8—C9 | 1.438 (6) | C42—H42 | 0.9500 |
C8—H8 | 0.9500 | C43—C44 | 1.387 (7) |
C9—C10 | 1.388 (6) | C43—H43 | 0.9500 |
C10—C11 | 1.396 (5) | C44—C45 | 1.386 (7) |
C10—C53 | 1.501 (6) | C44—C47 | 1.488 (7) |
C11—C12 | 1.439 (6) | C45—C46 | 1.386 (8) |
C12—C13 | 1.352 (6) | C45—H45 | 0.9500 |
C12—H12 | 0.9500 | C46—H46 | 0.9500 |
C13—C14 | 1.432 (6) | C47—C52 | 1.399 (6) |
C13—H13 | 0.9500 | C47—C48 | 1.404 (7) |
C14—C15 | 1.390 (6) | C48—C49 | 1.394 (7) |
C15—C16 | 1.397 (6) | C49—C50 | 1.388 (7) |
C15—C59 | 1.493 (5) | C49—H49 | 0.9500 |
C16—C17 | 1.448 (5) | C50—C51 | 1.387 (10) |
C17—C18 | 1.336 (6) | C50—H50 | 0.9500 |
C17—H17 | 0.9500 | C51—C52 | 1.352 (9) |
C18—C19 | 1.440 (5) | C51—H51 | 0.9500 |
C18—H18 | 0.9500 | C52—H52 | 0.9500 |
C19—C20 | 1.396 (5) | C53—C54 | 1.382 (6) |
C20—C48 | 1.489 (6) | C53—C58 | 1.385 (7) |
C21—C26 | 1.396 (6) | C54—F1 | 1.334 (5) |
C21—C22 | 1.397 (6) | C54—C55 | 1.379 (6) |
C22—C23 | 1.394 (7) | C55—F2 | 1.345 (6) |
C22—C27 | 1.496 (7) | C55—C56 | 1.348 (8) |
C23—C24 | 1.374 (9) | C56—C57 | 1.344 (8) |
C23—H23 | 0.9500 | C56—F3 | 1.348 (5) |
C24—C25 | 1.380 (8) | C57—F4 | 1.349 (6) |
C24—H24 | 0.9500 | C57—C58 | 1.379 (7) |
C25—C26 | 1.378 (6) | C58—F5 | 1.335 (6) |
C25—H25 | 0.9500 | C59—C60 | 1.376 (6) |
C26—H26 | 0.9500 | C59—C64 | 1.386 (6) |
C27—C28 | 1.381 (7) | C60—F6 | 1.351 (5) |
C27—C32 | 1.395 (7) | C60—C61 | 1.376 (6) |
C28—C29 | 1.392 (8) | C61—F7 | 1.336 (5) |
C28—H28 | 0.9500 | C61—C62 | 1.369 (6) |
C29—C30 | 1.388 (8) | C62—F8 | 1.344 (5) |
C29—H29 | 0.9500 | C62—C63 | 1.370 (7) |
C30—C31 | 1.391 (7) | C63—F9 | 1.341 (5) |
C30—C33 | 1.490 (7) | C63—C64 | 1.375 (6) |
C31—C32 | 1.368 (7) | C64—F10 | 1.343 (5) |
C31—H31 | 0.9500 | | |
| | | |
N2—Ni1—N4 | 166.13 (12) | C30—C31—H31 | 119.2 |
N2—Ni1—N3 | 89.64 (13) | C31—C32—C27 | 120.8 (5) |
N4—Ni1—N3 | 89.52 (12) | C31—C32—H32 | 119.6 |
N2—Ni1—N1 | 89.02 (12) | C27—C32—H32 | 119.6 |
N4—Ni1—N1 | 88.62 (12) | C30—C33—S1 | 112.3 (3) |
N3—Ni1—N1 | 166.68 (13) | C30—C33—H33A | 109.1 |
N2—Ni1—N5 | 95.43 (13) | S1—C33—H33A | 109.1 |
N4—Ni1—N5 | 98.38 (13) | C30—C33—H33B | 109.1 |
N3—Ni1—N5 | 88.44 (14) | S1—C33—H33B | 109.1 |
N1—Ni1—N5 | 104.88 (13) | H33A—C33—H33B | 107.9 |
C1—N1—C4 | 106.2 (3) | C34—S1—C33 | 100.7 (2) |
C1—N1—Ni1 | 126.7 (2) | C35—C34—C38 | 119.9 (4) |
C4—N1—Ni1 | 126.6 (2) | C35—C34—S1 | 118.1 (4) |
C6—N2—C9 | 106.1 (3) | C38—C34—S1 | 122.0 (3) |
C6—N2—Ni1 | 127.5 (3) | N5—C35—C34 | 123.0 (4) |
C9—N2—Ni1 | 125.3 (3) | N5—C35—H35 | 118.5 |
C11—N3—C14 | 106.2 (3) | C34—C35—H35 | 118.5 |
C11—N3—Ni1 | 125.8 (2) | C36—N5—C35 | 117.1 (4) |
C14—N3—Ni1 | 127.2 (3) | C36—N5—Ni1 | 119.5 (3) |
C19—N4—C16 | 106.0 (3) | C35—N5—Ni1 | 121.4 (3) |
C19—N4—Ni1 | 127.2 (2) | N5—C36—C37 | 124.0 (4) |
C16—N4—Ni1 | 126.8 (3) | N5—C36—H36 | 118.0 |
N1—C1—C20 | 125.4 (4) | C37—C36—H36 | 118.0 |
N1—C1—C2 | 110.4 (3) | C36—C37—C38 | 119.7 (4) |
C20—C1—C2 | 124.2 (4) | C36—C37—S2 | 118.1 (3) |
C3—C2—C1 | 106.8 (4) | C38—C37—S2 | 122.2 (4) |
C3—C2—H2 | 126.6 | C34—C38—C37 | 116.3 (4) |
C1—C2—H2 | 126.6 | C34—C38—C39 | 121.9 (4) |
C2—C3—C4 | 107.2 (4) | C37—C38—C39 | 121.7 (4) |
C2—C3—H3 | 126.4 | C38—C39—H39A | 109.5 |
C4—C3—H3 | 126.4 | C38—C39—H39B | 109.5 |
N1—C4—C5 | 126.2 (3) | H39A—C39—H39B | 109.5 |
N1—C4—C3 | 109.4 (3) | C38—C39—H39C | 109.5 |
C5—C4—C3 | 124.4 (3) | H39A—C39—H39C | 109.5 |
C4—C5—C6 | 124.8 (3) | H39B—C39—H39C | 109.5 |
C4—C5—C21 | 115.4 (3) | C37—S2—C40 | 99.6 (3) |
C6—C5—C21 | 119.7 (3) | C41—C40—S2 | 113.8 (4) |
N2—C6—C5 | 125.1 (3) | C41—C40—H40A | 108.8 |
N2—C6—C7 | 110.1 (4) | S2—C40—H40A | 108.8 |
C5—C6—C7 | 124.7 (3) | C41—C40—H40B | 108.8 |
C8—C7—C6 | 106.9 (3) | S2—C40—H40B | 108.8 |
C8—C7—H7 | 126.6 | H40A—C40—H40B | 107.7 |
C6—C7—H7 | 126.6 | C42—C41—C46 | 118.2 (6) |
C7—C8—C9 | 107.5 (4) | C42—C41—C40 | 122.5 (5) |
C7—C8—H8 | 126.2 | C46—C41—C40 | 119.3 (5) |
C9—C8—H8 | 126.2 | C41—C42—C43 | 121.6 (5) |
N2—C9—C10 | 125.0 (4) | C41—C42—H42 | 119.2 |
N2—C9—C8 | 109.5 (3) | C43—C42—H42 | 119.2 |
C10—C9—C8 | 125.5 (4) | C42—C43—C44 | 120.6 (5) |
C9—C10—C11 | 126.7 (4) | C42—C43—H43 | 119.7 |
C9—C10—C53 | 117.3 (3) | C44—C43—H43 | 119.7 |
C11—C10—C53 | 116.1 (3) | C45—C44—C43 | 117.8 (5) |
N3—C11—C10 | 124.1 (3) | C45—C44—C47 | 121.0 (4) |
N3—C11—C12 | 109.9 (3) | C43—C44—C47 | 121.2 (5) |
C10—C11—C12 | 126.0 (4) | C44—C45—C46 | 121.6 (5) |
C13—C12—C11 | 106.7 (4) | C44—C45—H45 | 119.2 |
C13—C12—H12 | 126.7 | C46—C45—H45 | 119.2 |
C11—C12—H12 | 126.7 | C45—C46—C41 | 120.2 (5) |
C12—C13—C14 | 107.5 (4) | C45—C46—H46 | 119.9 |
C12—C13—H13 | 126.2 | C41—C46—H46 | 119.9 |
C14—C13—H13 | 126.2 | C52—C47—C48 | 118.7 (5) |
N3—C14—C15 | 124.9 (4) | C52—C47—C44 | 120.8 (5) |
N3—C14—C13 | 109.6 (4) | C48—C47—C44 | 120.4 (4) |
C15—C14—C13 | 125.4 (4) | C49—C48—C47 | 119.7 (4) |
C14—C15—C16 | 125.7 (3) | C49—C48—C20 | 119.7 (4) |
C14—C15—C59 | 117.7 (4) | C47—C48—C20 | 120.5 (4) |
C16—C15—C59 | 116.6 (3) | C50—C49—C48 | 119.7 (6) |
N4—C16—C15 | 125.5 (3) | C50—C49—H49 | 120.2 |
N4—C16—C17 | 109.7 (3) | C48—C49—H49 | 120.2 |
C15—C16—C17 | 124.7 (3) | C51—C50—C49 | 120.2 (6) |
C18—C17—C16 | 107.0 (3) | C51—C50—H50 | 119.9 |
C18—C17—H17 | 126.5 | C49—C50—H50 | 119.9 |
C16—C17—H17 | 126.5 | C52—C51—C50 | 120.3 (5) |
C17—C18—C19 | 107.4 (4) | C52—C51—H51 | 119.9 |
C17—C18—H18 | 126.3 | C50—C51—H51 | 119.9 |
C19—C18—H18 | 126.3 | C51—C52—C47 | 121.3 (5) |
N4—C19—C20 | 125.5 (3) | C51—C52—H52 | 119.4 |
N4—C19—C18 | 109.9 (3) | C47—C52—H52 | 119.4 |
C20—C19—C18 | 124.6 (4) | C54—C53—C58 | 115.7 (4) |
C19—C20—C1 | 124.5 (4) | C54—C53—C10 | 122.5 (4) |
C19—C20—C48 | 117.8 (3) | C58—C53—C10 | 121.8 (4) |
C1—C20—C48 | 117.6 (4) | F1—C54—C55 | 117.5 (4) |
C26—C21—C22 | 119.9 (4) | F1—C54—C53 | 120.0 (4) |
C26—C21—C5 | 119.2 (3) | C55—C54—C53 | 122.5 (4) |
C22—C21—C5 | 120.7 (4) | F2—C55—C56 | 119.5 (4) |
C23—C22—C21 | 118.4 (5) | F2—C55—C54 | 120.9 (5) |
C23—C22—C27 | 121.8 (4) | C56—C55—C54 | 119.6 (5) |
C21—C22—C27 | 119.8 (4) | C57—C56—F3 | 120.1 (5) |
C24—C23—C22 | 121.2 (5) | C57—C56—C55 | 120.1 (4) |
C24—C23—H23 | 119.4 | F3—C56—C55 | 119.7 (5) |
C22—C23—H23 | 119.4 | C56—C57—F4 | 120.9 (5) |
C23—C24—C25 | 120.2 (5) | C56—C57—C58 | 120.6 (5) |
C23—C24—H24 | 119.9 | F4—C57—C58 | 118.5 (5) |
C25—C24—H24 | 119.9 | F5—C58—C57 | 119.9 (5) |
C26—C25—C24 | 119.8 (5) | F5—C58—C53 | 118.6 (4) |
C26—C25—H25 | 120.1 | C57—C58—C53 | 121.5 (5) |
C24—C25—H25 | 120.1 | C60—C59—C64 | 115.7 (4) |
C25—C26—C21 | 120.5 (4) | C60—C59—C15 | 122.1 (4) |
C25—C26—H26 | 119.8 | C64—C59—C15 | 122.1 (4) |
C21—C26—H26 | 119.8 | F6—C60—C59 | 118.8 (4) |
C28—C27—C32 | 118.3 (5) | F6—C60—C61 | 117.8 (4) |
C28—C27—C22 | 123.1 (4) | C59—C60—C61 | 123.4 (4) |
C32—C27—C22 | 118.4 (4) | F7—C61—C62 | 120.1 (4) |
C27—C28—C29 | 120.4 (5) | F7—C61—C60 | 121.1 (4) |
C27—C28—H28 | 119.8 | C62—C61—C60 | 118.8 (4) |
C29—C28—H28 | 119.8 | F8—C62—C61 | 119.6 (4) |
C30—C29—C28 | 121.3 (5) | F8—C62—C63 | 120.3 (4) |
C30—C29—H29 | 119.4 | C61—C62—C63 | 120.1 (4) |
C28—C29—H29 | 119.4 | F9—C63—C62 | 119.7 (4) |
C29—C30—C31 | 117.4 (5) | F9—C63—C64 | 120.7 (4) |
C29—C30—C33 | 122.0 (5) | C62—C63—C64 | 119.6 (4) |
C31—C30—C33 | 120.6 (5) | F10—C64—C63 | 118.3 (4) |
C32—C31—C30 | 121.6 (5) | F10—C64—C59 | 119.3 (4) |
C32—C31—H31 | 119.2 | C63—C64—C59 | 122.3 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C33—H33B···F8i | 0.99 | 2.63 | 3.592 (6) | 164 |
C35—H35···N2 | 0.95 | 2.58 | 3.125 (5) | 117 |
C36—H36···N4 | 0.95 | 2.60 | 3.206 (5) | 122 |
Symmetry code: (i) −x+3/2, −y+1, z+1/2. |