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The title compound consists of discrete complexes with a square-pyramidal NiN5 coordination polyhedron for the metal ions. The complexes are linked by C—H...F hydrogen bonds into chains propagating along [001].

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S2056989019012453/hb7846sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S2056989019012453/hb7846Isup2.hkl
Contains datablock I

CCDC reference: 1951945

Key indicators

  • Single-crystal X-ray study
  • T = 170 K
  • Mean [sigma](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

Computing details top

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 m3
Mr = 1184.78Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 44396 reflections
a = 12.6269 (2) Åθ = 1.4–27.0°
b = 18.0525 (3) ŵ = 0.49 mm1
c = 24.9524 (6) ÅT = 170 K
V = 5687.83 (19) Å3Block, red
Z = 40.15 × 0.10 × 0.05 mm
F(000) = 2408
Data collection top
Stoe IPDS-2
diffractometer
10468 reflections with I > 2σ(I)
ω scansRint = 0.055
Absorption correction: numerical
(X-Red and X-Shape; Stoe, 2008)
θmax = 27.0°, θmin = 1.4°
Tmin = 0.810, Tmax = 0.965h = 1614
44401 measured reflectionsk = 2320
12417 independent reflectionsl = 3131
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.04Δρmax = 0.34 e Å3
12417 reflectionsΔρmin = 0.39 e Å3
740 parametersAbsolute structure: Flack x determined using 4043 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013)
0 restraintsAbsolute 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
xyzUiso*/Ueq
Ni10.36866 (4)0.61346 (3)0.57341 (2)0.03235 (11)
N10.3385 (2)0.71635 (17)0.60371 (11)0.0329 (7)
N20.2384 (3)0.57504 (17)0.61227 (12)0.0340 (7)
N30.3742 (3)0.51813 (17)0.52990 (11)0.0374 (7)
N40.4729 (3)0.66068 (18)0.52138 (11)0.0337 (7)
C10.3978 (3)0.7789 (2)0.59612 (14)0.0361 (8)
C20.3622 (4)0.8368 (2)0.63062 (15)0.0411 (8)
H20.39160.88510.63360.049*
C30.2787 (3)0.8098 (2)0.65832 (15)0.0385 (8)
H30.23760.83580.68410.046*
C40.2636 (3)0.7342 (2)0.64145 (14)0.0335 (8)
C50.1883 (3)0.6867 (2)0.66275 (14)0.0348 (8)
C60.1780 (3)0.6117 (2)0.64944 (13)0.0342 (7)
C70.1072 (3)0.5608 (2)0.67541 (15)0.0387 (9)
H70.05740.57240.70270.046*
C80.1249 (4)0.4939 (2)0.65372 (15)0.0429 (9)
H80.08980.44910.66290.052*
C90.2067 (3)0.5023 (2)0.61405 (15)0.0378 (8)
C100.2491 (3)0.4457 (2)0.58317 (14)0.0382 (8)
C110.3253 (3)0.4528 (2)0.54297 (15)0.0388 (8)
C120.3605 (4)0.3948 (2)0.50759 (17)0.0496 (10)
H120.33920.34440.50840.060*
C130.4297 (4)0.4262 (3)0.47302 (17)0.0497 (10)
H130.46500.40190.44430.060*
C140.4400 (3)0.5026 (2)0.48752 (15)0.0385 (8)
C150.5083 (3)0.5531 (2)0.46350 (14)0.0382 (8)
C160.5222 (3)0.6268 (2)0.47900 (13)0.0342 (8)
C170.5939 (3)0.6784 (2)0.45336 (16)0.0423 (9)
H170.63760.66870.42320.051*
C180.5869 (3)0.7423 (2)0.48022 (15)0.0417 (9)
H180.62470.78650.47260.050*
C190.5114 (3)0.7316 (2)0.52279 (14)0.0359 (8)
C200.4805 (3)0.7864 (2)0.55899 (14)0.0368 (8)
C210.1169 (3)0.7200 (2)0.70420 (15)0.0385 (8)
C220.1413 (4)0.7145 (3)0.75868 (16)0.0480 (10)
C230.0784 (5)0.7530 (3)0.7952 (2)0.0701 (16)
H230.09420.75010.83240.084*
C240.0060 (5)0.7952 (3)0.7784 (2)0.0754 (17)
H240.04650.82210.80390.090*
C250.0319 (5)0.7984 (3)0.7248 (2)0.0630 (14)
H250.09180.82610.71340.076*
C260.0293 (4)0.7613 (3)0.68774 (18)0.0481 (10)
H260.01180.76390.65080.058*
C270.2296 (4)0.6651 (3)0.77658 (16)0.0495 (11)
C280.3349 (4)0.6799 (3)0.76606 (18)0.0562 (12)
H280.35440.72600.75060.067*
C290.4124 (4)0.6277 (3)0.77794 (18)0.0589 (13)
H290.48470.63930.77160.071*
C300.3863 (4)0.5589 (3)0.79893 (17)0.0572 (12)
C310.2806 (4)0.5464 (3)0.8117 (2)0.0631 (14)
H310.26110.50110.82840.076*
C320.2040 (4)0.5979 (3)0.80093 (18)0.0584 (13)
H320.13240.58780.81010.070*
C330.4666 (4)0.4992 (4)0.80592 (18)0.0669 (15)
H33A0.45550.47480.84100.080*
H33B0.53820.52150.80610.080*
S10.45960 (12)0.42922 (8)0.75272 (5)0.0652 (4)
C340.5137 (4)0.4798 (3)0.69782 (17)0.0488 (10)
C350.4473 (4)0.5274 (2)0.67001 (16)0.0442 (10)
H350.37630.53290.68200.053*
N50.4788 (3)0.5663 (2)0.62680 (12)0.0397 (7)
C360.5793 (3)0.5587 (3)0.61168 (17)0.0449 (9)
H360.60280.58580.58130.054*
C370.6515 (4)0.5137 (3)0.63743 (17)0.0516 (11)
C380.6190 (4)0.4710 (3)0.68145 (17)0.0494 (10)
C390.6924 (5)0.4168 (3)0.7083 (2)0.0659 (14)
H39A0.67220.41130.74600.099*
H39B0.76530.43510.70600.099*
H39C0.68730.36870.69030.099*
S20.78309 (11)0.51140 (10)0.61283 (6)0.0702 (4)
C400.8384 (4)0.5904 (4)0.6494 (2)0.080 (2)
H40A0.82590.58300.68820.095*
H40B0.91590.59170.64360.095*
C410.7924 (4)0.6637 (4)0.63313 (19)0.0633 (14)
C420.7113 (4)0.6972 (4)0.66102 (18)0.0649 (15)
H420.68710.67540.69350.078*
C430.6643 (4)0.7615 (3)0.64298 (18)0.0607 (13)
H430.60770.78280.66270.073*
C440.6989 (4)0.7953 (3)0.59624 (17)0.0518 (11)
C450.7836 (4)0.7635 (3)0.5695 (2)0.0630 (13)
H450.81050.78670.53820.076*
C460.8301 (4)0.6984 (4)0.5873 (2)0.0658 (14)
H460.88780.67750.56810.079*
C470.6447 (4)0.8620 (3)0.57452 (17)0.0516 (10)
C480.5386 (4)0.8582 (2)0.55788 (16)0.0442 (10)
C490.4884 (5)0.9215 (3)0.53857 (18)0.0548 (12)
H490.41710.91900.52640.066*
C500.5429 (6)0.9883 (3)0.5372 (2)0.0734 (17)
H500.50771.03210.52590.088*
C510.6486 (6)0.9911 (3)0.5521 (2)0.0768 (19)
H510.68631.03660.54970.092*
C520.6982 (5)0.9296 (3)0.5701 (2)0.0661 (15)
H520.77070.93230.58000.079*
C530.2096 (4)0.3686 (2)0.59367 (16)0.0428 (9)
C540.1119 (4)0.3441 (2)0.57611 (18)0.0492 (10)
C550.0757 (4)0.2733 (3)0.58575 (19)0.0549 (12)
C560.1364 (5)0.2256 (2)0.6139 (2)0.0609 (12)
C570.2319 (5)0.2470 (3)0.6320 (2)0.0666 (14)
C580.2688 (4)0.3177 (3)0.6224 (2)0.0569 (12)
F10.0481 (3)0.38982 (19)0.54925 (13)0.0742 (9)
F20.0200 (3)0.25128 (18)0.56817 (14)0.0788 (9)
F30.0995 (3)0.15736 (17)0.62517 (16)0.0862 (11)
F40.2921 (4)0.2008 (2)0.6617 (2)0.1099 (15)
F50.3640 (3)0.33798 (18)0.64045 (15)0.0827 (10)
C590.5742 (3)0.5266 (2)0.41772 (15)0.0400 (9)
C600.6774 (3)0.5037 (3)0.42437 (17)0.0475 (9)
C610.7405 (4)0.4800 (3)0.38280 (17)0.0472 (10)
C620.6994 (4)0.4791 (2)0.33204 (16)0.0459 (10)
C630.5979 (4)0.5029 (3)0.32304 (15)0.0456 (10)
C640.5368 (3)0.5260 (3)0.36550 (16)0.0437 (9)
F60.7198 (2)0.5046 (2)0.47407 (10)0.0686 (8)
F70.8392 (2)0.4563 (2)0.39158 (12)0.0704 (9)
F80.7586 (2)0.45350 (17)0.29130 (10)0.0613 (7)
F90.5582 (3)0.50154 (19)0.27319 (10)0.0686 (8)
F100.4375 (2)0.54870 (18)0.35559 (10)0.0598 (7)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0320 (2)0.0340 (2)0.03107 (19)0.0007 (2)0.00063 (19)0.00143 (18)
N10.0336 (17)0.0328 (16)0.0324 (15)0.0034 (13)0.0006 (12)0.0022 (12)
N20.0353 (17)0.0312 (16)0.0354 (14)0.0007 (14)0.0009 (13)0.0008 (12)
N30.0395 (17)0.0364 (16)0.0364 (14)0.0033 (16)0.0048 (14)0.0013 (12)
N40.0329 (16)0.0352 (17)0.0330 (14)0.0004 (14)0.0005 (12)0.0007 (12)
C10.037 (2)0.0354 (19)0.0363 (16)0.0058 (16)0.0008 (14)0.0015 (15)
C20.042 (2)0.037 (2)0.0441 (19)0.0073 (19)0.0005 (18)0.0016 (15)
C30.039 (2)0.038 (2)0.0377 (18)0.0006 (18)0.0012 (16)0.0038 (15)
C40.0333 (19)0.0346 (19)0.0324 (16)0.0029 (16)0.0022 (14)0.0011 (14)
C50.033 (2)0.038 (2)0.0335 (17)0.0002 (16)0.0038 (14)0.0002 (15)
C60.0290 (16)0.0396 (19)0.0339 (16)0.0009 (18)0.0006 (13)0.0016 (16)
C70.037 (2)0.042 (2)0.0370 (17)0.0016 (17)0.0042 (15)0.0023 (16)
C80.044 (2)0.037 (2)0.0482 (19)0.006 (2)0.0050 (18)0.0063 (16)
C90.038 (2)0.035 (2)0.0404 (18)0.0072 (17)0.0003 (16)0.0038 (16)
C100.041 (2)0.0336 (19)0.0398 (19)0.0007 (17)0.0039 (16)0.0031 (15)
C110.043 (2)0.0299 (19)0.0438 (19)0.0038 (17)0.0031 (16)0.0017 (16)
C120.059 (3)0.036 (2)0.054 (2)0.005 (2)0.011 (2)0.0063 (18)
C130.057 (3)0.045 (2)0.047 (2)0.001 (2)0.011 (2)0.0063 (19)
C140.040 (2)0.037 (2)0.0382 (18)0.0011 (18)0.0052 (15)0.0037 (16)
C150.037 (2)0.044 (2)0.0340 (17)0.0013 (18)0.0035 (15)0.0002 (16)
C160.0361 (19)0.039 (2)0.0275 (15)0.0013 (16)0.0032 (13)0.0017 (14)
C170.042 (2)0.048 (2)0.0376 (19)0.0022 (19)0.0075 (16)0.0015 (17)
C180.040 (2)0.044 (2)0.0409 (19)0.0069 (18)0.0082 (16)0.0017 (17)
C190.036 (2)0.037 (2)0.0341 (17)0.0068 (17)0.0034 (15)0.0038 (15)
C200.036 (2)0.036 (2)0.0382 (18)0.0024 (16)0.0012 (15)0.0018 (15)
C210.036 (2)0.036 (2)0.0427 (18)0.0001 (17)0.0065 (16)0.0001 (15)
C220.051 (3)0.052 (2)0.0406 (19)0.000 (2)0.0085 (19)0.0008 (17)
C230.094 (4)0.073 (4)0.043 (2)0.013 (3)0.024 (3)0.003 (2)
C240.093 (4)0.070 (4)0.064 (3)0.030 (3)0.031 (3)0.001 (3)
C250.063 (3)0.054 (3)0.073 (3)0.020 (3)0.032 (3)0.011 (2)
C260.043 (2)0.049 (3)0.052 (2)0.008 (2)0.0078 (19)0.0059 (19)
C270.051 (3)0.062 (3)0.0351 (19)0.000 (2)0.0004 (18)0.0011 (18)
C280.051 (3)0.069 (3)0.049 (2)0.007 (2)0.000 (2)0.004 (2)
C290.047 (3)0.085 (4)0.045 (2)0.006 (3)0.0011 (19)0.006 (2)
C300.048 (3)0.084 (4)0.039 (2)0.004 (3)0.0033 (19)0.011 (2)
C310.052 (3)0.083 (4)0.054 (3)0.002 (3)0.001 (2)0.027 (3)
C320.045 (2)0.080 (4)0.050 (2)0.003 (3)0.0022 (19)0.020 (2)
C330.053 (3)0.106 (4)0.042 (2)0.014 (3)0.003 (2)0.021 (3)
S10.0664 (8)0.0700 (9)0.0591 (7)0.0039 (7)0.0009 (6)0.0279 (6)
C340.051 (3)0.052 (3)0.043 (2)0.004 (2)0.0077 (18)0.0050 (18)
C350.043 (2)0.049 (2)0.0407 (19)0.002 (2)0.0030 (17)0.0088 (17)
N50.0358 (18)0.048 (2)0.0354 (15)0.0004 (15)0.0022 (13)0.0080 (14)
C360.037 (2)0.054 (3)0.044 (2)0.006 (2)0.0011 (17)0.0080 (19)
C370.045 (3)0.062 (3)0.048 (2)0.011 (2)0.0038 (18)0.004 (2)
C380.047 (3)0.052 (3)0.049 (2)0.009 (2)0.0077 (19)0.0036 (18)
C390.065 (3)0.064 (3)0.068 (3)0.018 (3)0.009 (3)0.015 (3)
S20.0454 (7)0.0985 (11)0.0666 (7)0.0231 (7)0.0050 (6)0.0145 (7)
C400.042 (3)0.130 (6)0.067 (3)0.006 (3)0.009 (2)0.023 (3)
C410.039 (2)0.100 (4)0.051 (2)0.006 (3)0.009 (2)0.006 (3)
C420.049 (3)0.104 (4)0.042 (2)0.012 (3)0.004 (2)0.008 (3)
C430.051 (3)0.090 (4)0.041 (2)0.012 (3)0.0000 (19)0.001 (2)
C440.041 (2)0.072 (3)0.043 (2)0.015 (2)0.0008 (18)0.005 (2)
C450.046 (3)0.088 (4)0.055 (2)0.011 (3)0.009 (2)0.004 (3)
C460.038 (2)0.099 (4)0.061 (3)0.010 (3)0.005 (2)0.005 (3)
C470.052 (3)0.059 (3)0.0435 (19)0.020 (2)0.013 (2)0.005 (2)
C480.047 (2)0.042 (2)0.043 (2)0.0123 (19)0.0121 (17)0.0017 (16)
C490.069 (3)0.043 (2)0.052 (2)0.007 (2)0.012 (2)0.003 (2)
C500.110 (5)0.043 (3)0.067 (3)0.013 (3)0.025 (3)0.001 (2)
C510.106 (5)0.053 (3)0.071 (3)0.041 (4)0.031 (3)0.009 (3)
C520.071 (3)0.074 (4)0.053 (2)0.038 (3)0.013 (3)0.016 (3)
C530.047 (2)0.037 (2)0.0452 (19)0.0023 (18)0.0059 (18)0.0032 (16)
C540.060 (3)0.042 (2)0.046 (2)0.010 (2)0.002 (2)0.0081 (19)
C550.064 (3)0.044 (2)0.057 (3)0.018 (2)0.001 (2)0.002 (2)
C560.074 (3)0.030 (2)0.079 (3)0.012 (2)0.008 (3)0.005 (2)
C570.067 (3)0.038 (2)0.095 (4)0.007 (2)0.007 (3)0.021 (2)
C580.048 (3)0.046 (3)0.077 (3)0.000 (2)0.000 (2)0.005 (2)
F10.075 (2)0.0631 (18)0.0844 (19)0.0207 (18)0.0285 (16)0.0286 (16)
F20.082 (2)0.0674 (19)0.087 (2)0.0361 (17)0.0184 (19)0.0069 (17)
F30.104 (3)0.0368 (15)0.118 (3)0.0149 (17)0.003 (2)0.0147 (16)
F40.097 (3)0.057 (2)0.176 (4)0.007 (2)0.026 (3)0.049 (2)
F50.0599 (19)0.0634 (19)0.125 (3)0.0026 (18)0.026 (2)0.0207 (18)
C590.039 (2)0.043 (2)0.038 (2)0.0021 (17)0.0040 (15)0.0020 (16)
C600.043 (2)0.061 (3)0.0383 (18)0.001 (2)0.0013 (18)0.005 (2)
C610.038 (2)0.052 (3)0.051 (2)0.004 (2)0.0082 (18)0.0058 (19)
C620.051 (3)0.046 (2)0.041 (2)0.003 (2)0.0152 (18)0.0072 (17)
C630.053 (3)0.050 (2)0.0338 (18)0.006 (2)0.0047 (16)0.0030 (17)
C640.041 (2)0.050 (2)0.0411 (19)0.001 (2)0.0033 (17)0.0011 (17)
F60.0516 (16)0.110 (3)0.0438 (13)0.0159 (18)0.0031 (12)0.0095 (15)
F70.0442 (16)0.096 (2)0.0709 (17)0.0195 (16)0.0073 (13)0.0099 (16)
F80.0660 (18)0.0676 (18)0.0502 (14)0.0031 (15)0.0220 (13)0.0118 (12)
F90.0723 (19)0.096 (2)0.0375 (12)0.0010 (19)0.0001 (12)0.0108 (14)
F100.0475 (15)0.084 (2)0.0476 (13)0.0108 (15)0.0008 (11)0.0029 (13)
Geometric parameters (Å, º) top
Ni1—N22.031 (3)C32—H320.9500
Ni1—N42.036 (3)C33—S11.834 (6)
Ni1—N32.036 (3)C33—H33A0.9900
Ni1—N12.041 (3)C33—H33B0.9900
Ni1—N52.106 (3)S1—C341.782 (5)
N1—C11.368 (5)C34—C351.387 (6)
N1—C41.373 (5)C34—C381.401 (7)
N2—C61.371 (5)C35—N51.347 (5)
N2—C91.373 (5)C35—H350.9500
N3—C111.372 (5)N5—C361.331 (5)
N3—C141.374 (5)C36—C371.379 (6)
N4—C191.370 (5)C36—H360.9500
N4—C161.371 (5)C37—C381.403 (6)
C1—C201.402 (5)C37—S21.772 (5)
C1—C21.427 (6)C38—C391.505 (6)
C2—C31.352 (6)C39—H39A0.9800
C2—H20.9500C39—H39B0.9800
C3—C41.442 (5)C39—H39C0.9800
C3—H30.9500S2—C401.832 (7)
C4—C51.386 (5)C40—C411.501 (9)
C5—C61.400 (6)C40—H40A0.9900
C5—C211.498 (5)C40—H40B0.9900
C6—C71.435 (5)C41—C421.379 (8)
C7—C81.344 (6)C41—C461.388 (7)
C7—H70.9500C42—C431.379 (8)
C8—C91.438 (6)C42—H420.9500
C8—H80.9500C43—C441.387 (7)
C9—C101.388 (6)C43—H430.9500
C10—C111.396 (5)C44—C451.386 (7)
C10—C531.501 (6)C44—C471.488 (7)
C11—C121.439 (6)C45—C461.386 (8)
C12—C131.352 (6)C45—H450.9500
C12—H120.9500C46—H460.9500
C13—C141.432 (6)C47—C521.399 (6)
C13—H130.9500C47—C481.404 (7)
C14—C151.390 (6)C48—C491.394 (7)
C15—C161.397 (6)C49—C501.388 (7)
C15—C591.493 (5)C49—H490.9500
C16—C171.448 (5)C50—C511.387 (10)
C17—C181.336 (6)C50—H500.9500
C17—H170.9500C51—C521.352 (9)
C18—C191.440 (5)C51—H510.9500
C18—H180.9500C52—H520.9500
C19—C201.396 (5)C53—C541.382 (6)
C20—C481.489 (6)C53—C581.385 (7)
C21—C261.396 (6)C54—F11.334 (5)
C21—C221.397 (6)C54—C551.379 (6)
C22—C231.394 (7)C55—F21.345 (6)
C22—C271.496 (7)C55—C561.348 (8)
C23—C241.374 (9)C56—C571.344 (8)
C23—H230.9500C56—F31.348 (5)
C24—C251.380 (8)C57—F41.349 (6)
C24—H240.9500C57—C581.379 (7)
C25—C261.378 (6)C58—F51.335 (6)
C25—H250.9500C59—C601.376 (6)
C26—H260.9500C59—C641.386 (6)
C27—C281.381 (7)C60—F61.351 (5)
C27—C321.395 (7)C60—C611.376 (6)
C28—C291.392 (8)C61—F71.336 (5)
C28—H280.9500C61—C621.369 (6)
C29—C301.388 (8)C62—F81.344 (5)
C29—H290.9500C62—C631.370 (7)
C30—C311.391 (7)C63—F91.341 (5)
C30—C331.490 (7)C63—C641.375 (6)
C31—C321.368 (7)C64—F101.343 (5)
C31—H310.9500
N2—Ni1—N4166.13 (12)C30—C31—H31119.2
N2—Ni1—N389.64 (13)C31—C32—C27120.8 (5)
N4—Ni1—N389.52 (12)C31—C32—H32119.6
N2—Ni1—N189.02 (12)C27—C32—H32119.6
N4—Ni1—N188.62 (12)C30—C33—S1112.3 (3)
N3—Ni1—N1166.68 (13)C30—C33—H33A109.1
N2—Ni1—N595.43 (13)S1—C33—H33A109.1
N4—Ni1—N598.38 (13)C30—C33—H33B109.1
N3—Ni1—N588.44 (14)S1—C33—H33B109.1
N1—Ni1—N5104.88 (13)H33A—C33—H33B107.9
C1—N1—C4106.2 (3)C34—S1—C33100.7 (2)
C1—N1—Ni1126.7 (2)C35—C34—C38119.9 (4)
C4—N1—Ni1126.6 (2)C35—C34—S1118.1 (4)
C6—N2—C9106.1 (3)C38—C34—S1122.0 (3)
C6—N2—Ni1127.5 (3)N5—C35—C34123.0 (4)
C9—N2—Ni1125.3 (3)N5—C35—H35118.5
C11—N3—C14106.2 (3)C34—C35—H35118.5
C11—N3—Ni1125.8 (2)C36—N5—C35117.1 (4)
C14—N3—Ni1127.2 (3)C36—N5—Ni1119.5 (3)
C19—N4—C16106.0 (3)C35—N5—Ni1121.4 (3)
C19—N4—Ni1127.2 (2)N5—C36—C37124.0 (4)
C16—N4—Ni1126.8 (3)N5—C36—H36118.0
N1—C1—C20125.4 (4)C37—C36—H36118.0
N1—C1—C2110.4 (3)C36—C37—C38119.7 (4)
C20—C1—C2124.2 (4)C36—C37—S2118.1 (3)
C3—C2—C1106.8 (4)C38—C37—S2122.2 (4)
C3—C2—H2126.6C34—C38—C37116.3 (4)
C1—C2—H2126.6C34—C38—C39121.9 (4)
C2—C3—C4107.2 (4)C37—C38—C39121.7 (4)
C2—C3—H3126.4C38—C39—H39A109.5
C4—C3—H3126.4C38—C39—H39B109.5
N1—C4—C5126.2 (3)H39A—C39—H39B109.5
N1—C4—C3109.4 (3)C38—C39—H39C109.5
C5—C4—C3124.4 (3)H39A—C39—H39C109.5
C4—C5—C6124.8 (3)H39B—C39—H39C109.5
C4—C5—C21115.4 (3)C37—S2—C4099.6 (3)
C6—C5—C21119.7 (3)C41—C40—S2113.8 (4)
N2—C6—C5125.1 (3)C41—C40—H40A108.8
N2—C6—C7110.1 (4)S2—C40—H40A108.8
C5—C6—C7124.7 (3)C41—C40—H40B108.8
C8—C7—C6106.9 (3)S2—C40—H40B108.8
C8—C7—H7126.6H40A—C40—H40B107.7
C6—C7—H7126.6C42—C41—C46118.2 (6)
C7—C8—C9107.5 (4)C42—C41—C40122.5 (5)
C7—C8—H8126.2C46—C41—C40119.3 (5)
C9—C8—H8126.2C41—C42—C43121.6 (5)
N2—C9—C10125.0 (4)C41—C42—H42119.2
N2—C9—C8109.5 (3)C43—C42—H42119.2
C10—C9—C8125.5 (4)C42—C43—C44120.6 (5)
C9—C10—C11126.7 (4)C42—C43—H43119.7
C9—C10—C53117.3 (3)C44—C43—H43119.7
C11—C10—C53116.1 (3)C45—C44—C43117.8 (5)
N3—C11—C10124.1 (3)C45—C44—C47121.0 (4)
N3—C11—C12109.9 (3)C43—C44—C47121.2 (5)
C10—C11—C12126.0 (4)C44—C45—C46121.6 (5)
C13—C12—C11106.7 (4)C44—C45—H45119.2
C13—C12—H12126.7C46—C45—H45119.2
C11—C12—H12126.7C45—C46—C41120.2 (5)
C12—C13—C14107.5 (4)C45—C46—H46119.9
C12—C13—H13126.2C41—C46—H46119.9
C14—C13—H13126.2C52—C47—C48118.7 (5)
N3—C14—C15124.9 (4)C52—C47—C44120.8 (5)
N3—C14—C13109.6 (4)C48—C47—C44120.4 (4)
C15—C14—C13125.4 (4)C49—C48—C47119.7 (4)
C14—C15—C16125.7 (3)C49—C48—C20119.7 (4)
C14—C15—C59117.7 (4)C47—C48—C20120.5 (4)
C16—C15—C59116.6 (3)C50—C49—C48119.7 (6)
N4—C16—C15125.5 (3)C50—C49—H49120.2
N4—C16—C17109.7 (3)C48—C49—H49120.2
C15—C16—C17124.7 (3)C51—C50—C49120.2 (6)
C18—C17—C16107.0 (3)C51—C50—H50119.9
C18—C17—H17126.5C49—C50—H50119.9
C16—C17—H17126.5C52—C51—C50120.3 (5)
C17—C18—C19107.4 (4)C52—C51—H51119.9
C17—C18—H18126.3C50—C51—H51119.9
C19—C18—H18126.3C51—C52—C47121.3 (5)
N4—C19—C20125.5 (3)C51—C52—H52119.4
N4—C19—C18109.9 (3)C47—C52—H52119.4
C20—C19—C18124.6 (4)C54—C53—C58115.7 (4)
C19—C20—C1124.5 (4)C54—C53—C10122.5 (4)
C19—C20—C48117.8 (3)C58—C53—C10121.8 (4)
C1—C20—C48117.6 (4)F1—C54—C55117.5 (4)
C26—C21—C22119.9 (4)F1—C54—C53120.0 (4)
C26—C21—C5119.2 (3)C55—C54—C53122.5 (4)
C22—C21—C5120.7 (4)F2—C55—C56119.5 (4)
C23—C22—C21118.4 (5)F2—C55—C54120.9 (5)
C23—C22—C27121.8 (4)C56—C55—C54119.6 (5)
C21—C22—C27119.8 (4)C57—C56—F3120.1 (5)
C24—C23—C22121.2 (5)C57—C56—C55120.1 (4)
C24—C23—H23119.4F3—C56—C55119.7 (5)
C22—C23—H23119.4C56—C57—F4120.9 (5)
C23—C24—C25120.2 (5)C56—C57—C58120.6 (5)
C23—C24—H24119.9F4—C57—C58118.5 (5)
C25—C24—H24119.9F5—C58—C57119.9 (5)
C26—C25—C24119.8 (5)F5—C58—C53118.6 (4)
C26—C25—H25120.1C57—C58—C53121.5 (5)
C24—C25—H25120.1C60—C59—C64115.7 (4)
C25—C26—C21120.5 (4)C60—C59—C15122.1 (4)
C25—C26—H26119.8C64—C59—C15122.1 (4)
C21—C26—H26119.8F6—C60—C59118.8 (4)
C28—C27—C32118.3 (5)F6—C60—C61117.8 (4)
C28—C27—C22123.1 (4)C59—C60—C61123.4 (4)
C32—C27—C22118.4 (4)F7—C61—C62120.1 (4)
C27—C28—C29120.4 (5)F7—C61—C60121.1 (4)
C27—C28—H28119.8C62—C61—C60118.8 (4)
C29—C28—H28119.8F8—C62—C61119.6 (4)
C30—C29—C28121.3 (5)F8—C62—C63120.3 (4)
C30—C29—H29119.4C61—C62—C63120.1 (4)
C28—C29—H29119.4F9—C63—C62119.7 (4)
C29—C30—C31117.4 (5)F9—C63—C64120.7 (4)
C29—C30—C33122.0 (5)C62—C63—C64119.6 (4)
C31—C30—C33120.6 (5)F10—C64—C63118.3 (4)
C32—C31—C30121.6 (5)F10—C64—C59119.3 (4)
C32—C31—H31119.2C63—C64—C59122.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C33—H33B···F8i0.992.633.592 (6)164
C35—H35···N20.952.583.125 (5)117
C36—H36···N40.952.603.206 (5)122
Symmetry code: (i) x+3/2, y+1, z+1/2.
 

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