cis-Bis{1,1-dibenzyl-3-[(furan-2-yl)carbon-yl]thio-ureato-κO,S}nickel(II).

In the title compound, [Ni(C(20)H(17)N(2)O(2)S)(2)], the Ni(II) atom is coordinated by the S and O atoms of two 1,1-dibenzyl-3-[(furan-2-yl)carbon-yl]thio-ureate ligands in a distorted square-planar geometry. The two O and two S atoms are mutually cis to each other. The Ni-S and Ni-O bond lengths lie within the range of those found in related structures. The dihedral angle between the planes of the two chelating rings is 20.33 (6)°.

Related literature

For general background to transition metal complexes with N-acyl disubstituted thio­ureas, see: Arslan et al. (2003 ▶). For details of the synthesis, see: Nagasawa & Mitsunobu (1981 ▶). For related structures, see: Binzet et al. (2009 ▶); Ozer et al. (2009 ▶); Pérez et al. (2009 ▶).

Experimental

Crystal data

[Ni(C20H17N2O2S)2]

M = 757.54

Monoclinic,

a = 18.7260 (4) Å

b = 10.8430 (2) Å

c = 19.6490 (5) Å

β = 114.628 (1)°

V = 3626.72 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.70 mm−1

T = 293 K

0.38 × 0.27 × 0.19 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: Gaussian (Coppens et al., 1965 ▶) T min = 0.779, T max = 0.886

28443 measured reflections

7636 independent reflections

6155 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.09

7636 reflections

460 parameters

H-atom parameters constrained

Δρmax = 0.30 e Å−3

Δρmin = −0.55 e Å−3

Data collection: COLLECT (Enraf–Nonius, 2000 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811010749/bt5498sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811010749/bt5498Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C20H17N2O2S)2]	F(000) = 1576
Mr = 757.54	Dx = 1.387 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 16796 reflections
a = 18.7260 (4) Å	θ = 2.9–27.1°
b = 10.8430 (2) Å	µ = 0.70 mm−1
c = 19.6490 (5) Å	T = 293 K
β = 114.628 (1)°	Prism, blue
V = 3626.72 (14) Å3	0.38 × 0.27 × 0.19 mm
Z = 4

Nonius KappaCCD diffractometer	7636 independent reflections
Radiation source: Enraf Nonius FR590	6155 reflections with I > 2σ(I)
graphite	Rint = 0.058
Detector resolution: 9 pixels mm-1	θmax = 27.1°, θmin = 3.0°
CCD rotation images, thick slices scans	h = −23→23
Absorption correction: gaussian (Coppens et al., 1965)	k = −13→11
Tmin = 0.779, Tmax = 0.886	l = −22→24
28443 measured reflections

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0504P)2 + 0.7766P] where P = (Fo2 + 2Fc2)/3
7636 reflections	(Δ/σ)max = 0.001
460 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.55 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
Ni	0.491462 (13)	0.08249 (2)	0.203939 (13)	0.04117 (9)
S1	0.45918 (4)	0.27092 (5)	0.17502 (4)	0.05827 (16)
S2	0.40661 (3)	0.08767 (5)	0.25086 (3)	0.05258 (14)
O1	0.54999 (8)	0.06931 (12)	0.14719 (8)	0.0473 (3)
O2	0.53333 (8)	−0.07065 (14)	0.24394 (9)	0.0540 (4)
O3	0.60150 (9)	−0.03183 (13)	0.05316 (9)	0.0580 (4)
O4	0.64021 (9)	−0.24664 (17)	0.30736 (10)	0.0699 (5)
N1	0.55377 (9)	0.26690 (14)	0.09920 (9)	0.0430 (3)
N2	0.52359 (9)	0.45372 (15)	0.13379 (9)	0.0419 (3)
N3	0.45963 (9)	−0.14303 (15)	0.30784 (9)	0.0451 (4)
N4	0.34078 (9)	−0.08247 (14)	0.30160 (9)	0.0427 (4)
C1	0.56213 (10)	0.14477 (17)	0.10394 (10)	0.0405 (4)
C2	0.51798 (10)	0.33035 (17)	0.13450 (10)	0.0407 (4)
C3	0.59370 (11)	0.09342 (17)	0.05366 (11)	0.0421 (4)
C4	0.61673 (14)	0.1442 (2)	0.00348 (13)	0.0581 (5)
H4	0.6167	0.2277	−0.0075	0.07*
C5	0.64091 (15)	0.0458 (2)	−0.02934 (14)	0.0653 (6)
H5	0.6604	0.0521	−0.0657	0.078*
C6	0.63044 (15)	−0.0570 (2)	0.00174 (14)	0.0623 (6)
H6	0.6414	−0.1358	−0.01	0.075*
C7	0.56076 (11)	0.51742 (18)	0.09058 (10)	0.0428 (4)
H7A	0.5256	0.5819	0.061	0.051*
H7B	0.5668	0.4589	0.056	0.051*
C8	0.63963 (11)	0.57404 (17)	0.13665 (10)	0.0415 (4)
C9	0.70500 (12)	0.5013 (2)	0.17242 (12)	0.0543 (5)
H9	0.6996	0.416	0.1713	0.065*
C10	0.77852 (13)	0.5534 (2)	0.21001 (14)	0.0639 (6)
H10	0.8223	0.5034	0.234	0.077*
C11	0.78655 (13)	0.6796 (3)	0.21171 (13)	0.0650 (6)
H11	0.836	0.715	0.2364	0.078*
C12	0.72184 (14)	0.7536 (2)	0.17704 (14)	0.0637 (6)
H12	0.7273	0.8389	0.1787	0.076*
C13	0.64831 (12)	0.70070 (19)	0.13954 (12)	0.0529 (5)
H13	0.6045	0.7508	0.1162	0.063*
C14	0.48762 (12)	0.53554 (18)	0.17003 (11)	0.0475 (4)
H14A	0.519	0.6099	0.1858	0.057*
H14B	0.4893	0.4951	0.2147	0.057*
C15	0.40373 (12)	0.57173 (17)	0.12178 (12)	0.0460 (4)
C16	0.35972 (12)	0.5213 (2)	0.05261 (12)	0.0538 (5)
H16	0.3815	0.4608	0.0335	0.065*
C17	0.28272 (15)	0.5602 (3)	0.01087 (16)	0.0717 (7)
H17	0.2536	0.5266	−0.0362	0.086*
C18	0.24990 (16)	0.6483 (3)	0.0393 (2)	0.0835 (9)
H18	0.1984	0.674	0.0117	0.1*
C19	0.29335 (18)	0.6984 (3)	0.1087 (2)	0.0778 (8)
H19	0.2712	0.7578	0.1281	0.093*
C20	0.36927 (15)	0.6610 (2)	0.14927 (15)	0.0622 (6)
H20	0.3983	0.6958	0.196	0.075*
C21	0.51974 (11)	−0.14077 (18)	0.28856 (10)	0.0427 (4)
C22	0.40345 (11)	−0.05635 (17)	0.28756 (10)	0.0413 (4)
C23	0.57549 (11)	−0.2412 (2)	0.32215 (11)	0.0484 (5)
C24	0.57399 (15)	−0.3381 (2)	0.36413 (13)	0.0627 (6)
H24	0.5358	−0.3555	0.3814	0.075*
C25	0.64210 (18)	−0.4084 (3)	0.37688 (16)	0.0794 (8)
H25	0.6575	−0.481	0.4043	0.095*
C26	0.67957 (16)	−0.3504 (3)	0.34200 (17)	0.0831 (8)
H26	0.7265	−0.377	0.3413	0.1*
C27	0.33271 (12)	−0.20135 (18)	0.33465 (11)	0.0472 (4)
H27A	0.3679	−0.2612	0.3283	0.057*
H27B	0.2794	−0.2315	0.308	0.057*
C28	0.35100 (12)	−0.19020 (18)	0.41685 (11)	0.0480 (4)
C29	0.42288 (15)	−0.1481 (3)	0.46681 (14)	0.0724 (7)
H29	0.4602	−0.1243	0.4497	0.087*
C30	0.44037 (19)	−0.1406 (4)	0.54257 (16)	0.0917 (9)
H30	0.489	−0.1107	0.5758	0.11*
C31	0.3866 (2)	−0.1768 (3)	0.56872 (15)	0.0846 (8)
H31	0.3987	−0.1723	0.6196	0.101*
C32	0.31511 (19)	−0.2196 (3)	0.52005 (16)	0.0800 (8)
H32	0.2785	−0.2444	0.5378	0.096*
C33	0.29656 (15)	−0.2262 (2)	0.44355 (14)	0.0649 (6)
H33	0.2475	−0.255	0.4105	0.078*
C34	0.27511 (11)	0.00250 (18)	0.28685 (11)	0.0458 (4)
H34A	0.2919	0.0857	0.2827	0.055*
H34B	0.2607	0.0006	0.3289	0.055*
C35	0.20404 (11)	−0.02923 (18)	0.21620 (11)	0.0450 (4)
C36	0.20390 (14)	−0.0134 (2)	0.14626 (13)	0.0603 (6)
H36	0.2484	0.017	0.1423	0.072*
C37	0.13797 (17)	−0.0426 (3)	0.08225 (15)	0.0767 (7)
H37	0.1384	−0.0317	0.0355	0.092*
C38	0.07181 (17)	−0.0875 (3)	0.08736 (17)	0.0780 (8)
H38	0.0275	−0.107	0.0442	0.094*
C39	0.07148 (15)	−0.1035 (3)	0.15642 (17)	0.0774 (7)
H39	0.0269	−0.1343	0.1601	0.093*
C40	0.13681 (14)	−0.0741 (2)	0.22024 (15)	0.0626 (6)
H40	0.1357	−0.0846	0.2668	0.075*

	U11	U22	U33	U12	U13	U23
Ni	0.03816 (14)	0.04489 (15)	0.04528 (16)	−0.00023 (9)	0.02215 (11)	0.00586 (10)
S1	0.0690 (3)	0.0462 (3)	0.0836 (4)	0.0072 (2)	0.0556 (3)	0.0105 (3)
S2	0.0562 (3)	0.0446 (3)	0.0736 (4)	0.0032 (2)	0.0436 (3)	0.0100 (2)
O1	0.0487 (7)	0.0472 (7)	0.0543 (8)	0.0060 (6)	0.0297 (7)	0.0107 (6)
O2	0.0510 (8)	0.0584 (9)	0.0628 (9)	0.0103 (6)	0.0338 (7)	0.0196 (7)
O3	0.0706 (10)	0.0444 (8)	0.0732 (10)	0.0086 (7)	0.0439 (8)	0.0062 (7)
O4	0.0584 (9)	0.0785 (11)	0.0826 (12)	0.0178 (8)	0.0391 (9)	0.0175 (9)
N1	0.0437 (8)	0.0431 (8)	0.0473 (9)	−0.0015 (7)	0.0240 (7)	0.0010 (7)
N2	0.0427 (8)	0.0418 (8)	0.0434 (8)	−0.0037 (6)	0.0202 (7)	−0.0024 (6)
N3	0.0449 (8)	0.0464 (9)	0.0481 (9)	0.0007 (7)	0.0233 (7)	0.0034 (7)
N4	0.0454 (8)	0.0411 (8)	0.0485 (9)	−0.0013 (6)	0.0263 (7)	0.0037 (7)
C1	0.0336 (8)	0.0457 (10)	0.0423 (10)	−0.0013 (7)	0.0160 (8)	0.0032 (8)
C2	0.0388 (9)	0.0436 (10)	0.0394 (9)	−0.0013 (7)	0.0160 (8)	0.0015 (8)
C3	0.0395 (9)	0.0404 (10)	0.0487 (11)	0.0000 (7)	0.0206 (8)	0.0019 (8)
C4	0.0750 (14)	0.0520 (12)	0.0632 (14)	−0.0024 (11)	0.0446 (12)	0.0032 (10)
C5	0.0773 (16)	0.0704 (15)	0.0661 (15)	0.0000 (12)	0.0478 (13)	−0.0058 (12)
C6	0.0677 (14)	0.0601 (14)	0.0692 (15)	0.0090 (11)	0.0384 (12)	−0.0090 (11)
C7	0.0430 (9)	0.0452 (10)	0.0378 (9)	−0.0056 (8)	0.0145 (8)	0.0024 (8)
C8	0.0408 (9)	0.0450 (10)	0.0390 (10)	−0.0036 (8)	0.0169 (8)	0.0004 (7)
C9	0.0483 (11)	0.0488 (11)	0.0607 (13)	0.0000 (9)	0.0177 (10)	−0.0017 (10)
C10	0.0408 (11)	0.0762 (16)	0.0655 (15)	0.0023 (10)	0.0132 (10)	−0.0016 (12)
C11	0.0485 (12)	0.0831 (17)	0.0576 (14)	−0.0205 (12)	0.0164 (11)	−0.0061 (12)
C12	0.0657 (14)	0.0516 (12)	0.0645 (14)	−0.0187 (11)	0.0177 (12)	−0.0018 (11)
C13	0.0513 (11)	0.0451 (11)	0.0558 (12)	−0.0041 (9)	0.0159 (10)	0.0033 (9)
C14	0.0545 (11)	0.0432 (10)	0.0479 (11)	−0.0028 (9)	0.0243 (9)	−0.0073 (8)
C15	0.0522 (11)	0.0392 (10)	0.0542 (12)	−0.0031 (8)	0.0296 (9)	0.0026 (8)
C16	0.0519 (11)	0.0547 (12)	0.0569 (13)	−0.0033 (9)	0.0245 (10)	0.0041 (10)
C17	0.0568 (13)	0.0806 (17)	0.0692 (16)	−0.0053 (12)	0.0180 (12)	0.0189 (13)
C18	0.0587 (14)	0.086 (2)	0.113 (2)	0.0181 (14)	0.0426 (17)	0.0433 (18)
C19	0.0799 (17)	0.0636 (15)	0.112 (2)	0.0207 (14)	0.0622 (18)	0.0204 (16)
C20	0.0729 (15)	0.0502 (12)	0.0766 (15)	0.0029 (11)	0.0440 (13)	−0.0004 (11)
C21	0.0415 (9)	0.0467 (10)	0.0406 (10)	−0.0008 (8)	0.0180 (8)	0.0007 (8)
C22	0.0442 (9)	0.0437 (10)	0.0416 (10)	−0.0039 (8)	0.0235 (8)	−0.0010 (8)
C23	0.0456 (10)	0.0560 (12)	0.0460 (11)	0.0051 (9)	0.0214 (9)	0.0032 (9)
C24	0.0737 (15)	0.0620 (14)	0.0599 (14)	0.0151 (11)	0.0353 (12)	0.0176 (11)
C25	0.095 (2)	0.0741 (17)	0.0690 (17)	0.0361 (15)	0.0340 (16)	0.0267 (13)
C26	0.0686 (16)	0.094 (2)	0.0869 (19)	0.0386 (15)	0.0327 (15)	0.0181 (16)
C27	0.0519 (11)	0.0422 (10)	0.0548 (12)	−0.0049 (8)	0.0296 (9)	0.0026 (8)
C28	0.0536 (11)	0.0435 (10)	0.0526 (11)	0.0001 (9)	0.0276 (9)	0.0072 (9)
C29	0.0638 (14)	0.096 (2)	0.0567 (14)	−0.0132 (14)	0.0248 (12)	0.0092 (13)
C30	0.0836 (19)	0.122 (3)	0.0550 (16)	−0.0111 (18)	0.0142 (14)	0.0108 (16)
C31	0.106 (2)	0.100 (2)	0.0527 (15)	0.0116 (18)	0.0377 (16)	0.0133 (14)
C32	0.097 (2)	0.094 (2)	0.0723 (18)	0.0048 (16)	0.0578 (17)	0.0112 (15)
C33	0.0686 (14)	0.0697 (15)	0.0710 (15)	−0.0074 (12)	0.0438 (13)	−0.0002 (12)
C34	0.0508 (10)	0.0452 (10)	0.0535 (11)	0.0010 (8)	0.0337 (9)	0.0007 (9)
C35	0.0479 (10)	0.0400 (10)	0.0540 (11)	0.0047 (8)	0.0281 (9)	0.0027 (8)
C36	0.0641 (13)	0.0669 (14)	0.0586 (13)	0.0011 (11)	0.0343 (11)	0.0053 (11)
C37	0.0829 (18)	0.0895 (19)	0.0533 (14)	0.0033 (15)	0.0240 (13)	0.0070 (13)
C38	0.0657 (16)	0.0734 (17)	0.0733 (18)	−0.0039 (13)	0.0077 (14)	0.0046 (13)
C39	0.0535 (13)	0.0853 (19)	0.088 (2)	−0.0106 (12)	0.0240 (14)	0.0065 (15)
C40	0.0557 (13)	0.0707 (15)	0.0687 (15)	−0.0070 (11)	0.0332 (12)	0.0066 (12)

Ni—O2	1.8645 (14)	C15—C16	1.375 (3)
Ni—O1	1.8664 (13)	C15—C20	1.391 (3)
Ni—S1	2.1392 (6)	C16—C17	1.394 (3)
Ni—S2	2.1444 (5)	C16—H16	0.93
S1—C2	1.7296 (18)	C17—C18	1.374 (4)
S2—C22	1.7314 (19)	C17—H17	0.93
O1—C1	1.267 (2)	C18—C19	1.376 (5)
O2—C21	1.264 (2)	C18—H18	0.93
O3—C6	1.359 (3)	C19—C20	1.370 (4)
O3—C3	1.366 (2)	C19—H19	0.93
O4—C23	1.360 (2)	C20—H20	0.93
O4—C26	1.361 (3)	C21—C23	1.462 (3)
N1—C1	1.332 (2)	C23—C24	1.343 (3)
N1—C2	1.338 (2)	C24—C25	1.416 (3)
N2—C2	1.342 (2)	C24—H24	0.93
N2—C14	1.465 (2)	C25—C26	1.326 (4)
N2—C7	1.475 (2)	C25—H25	0.93
N3—C21	1.329 (2)	C26—H26	0.93
N3—C22	1.342 (2)	C27—C28	1.510 (3)
N4—C22	1.343 (2)	C27—H27A	0.97
N4—C34	1.466 (2)	C27—H27B	0.97
N4—C27	1.479 (2)	C28—C29	1.372 (3)
C1—C3	1.457 (3)	C28—C33	1.383 (3)
C3—C4	1.348 (3)	C29—C30	1.387 (4)
C4—C5	1.415 (3)	C29—H29	0.93
C4—H4	0.93	C30—C31	1.366 (4)
C5—C6	1.325 (3)	C30—H30	0.93
C5—H5	0.93	C31—C32	1.361 (4)
C6—H6	0.93	C31—H31	0.93
C7—C8	1.504 (2)	C32—C33	1.397 (4)
C7—H7A	0.97	C32—H32	0.93
C7—H7B	0.97	C33—H33	0.93
C8—C9	1.377 (3)	C34—C35	1.509 (3)
C8—C13	1.381 (3)	C34—H34A	0.97
C9—C10	1.383 (3)	C34—H34B	0.97
C9—H9	0.93	C35—C40	1.383 (3)
C10—C11	1.376 (3)	C35—C36	1.384 (3)
C10—H10	0.93	C36—C37	1.383 (4)
C11—C12	1.374 (3)	C36—H36	0.93
C11—H11	0.93	C37—C38	1.373 (4)
C12—C13	1.386 (3)	C37—H37	0.93
C12—H12	0.93	C38—C39	1.370 (4)
C13—H13	0.93	C38—H38	0.93
C14—C15	1.510 (3)	C39—C40	1.376 (4)
C14—H14A	0.97	C39—H39	0.93
C14—H14B	0.97	C40—H40	0.93
O2—Ni—O1	86.28 (6)	C16—C17—H17	120
O2—Ni—S1	170.14 (6)	C19—C18—C17	119.8 (2)
O1—Ni—S1	94.92 (4)	C19—C18—H18	120.1
O2—Ni—S2	95.67 (4)	C17—C18—H18	120.1
O1—Ni—S2	169.62 (5)	C20—C19—C18	120.1 (3)
S1—Ni—S2	84.91 (2)	C20—C19—H19	120
C2—S1—Ni	108.33 (7)	C18—C19—H19	120
C22—S2—Ni	108.40 (6)	C19—C20—C15	121.2 (3)
C1—O1—Ni	131.73 (12)	C19—C20—H20	119.4
C21—O2—Ni	131.10 (13)	C15—C20—H20	119.4
C6—O3—C3	106.39 (16)	O2—C21—N3	130.40 (18)
C23—O4—C26	105.89 (19)	O2—C21—C23	116.69 (16)
C1—N1—C2	122.99 (16)	N3—C21—C23	112.81 (17)
C2—N2—C14	122.98 (15)	N3—C22—N4	115.81 (16)
C2—N2—C7	122.04 (15)	N3—C22—S2	126.65 (14)
C14—N2—C7	114.77 (16)	N4—C22—S2	117.41 (14)
C21—N3—C22	123.70 (16)	C24—C23—O4	110.23 (19)
C22—N4—C34	124.04 (15)	C24—C23—C21	131.78 (19)
C22—N4—C27	122.13 (16)	O4—C23—C21	117.90 (17)
C34—N4—C27	113.82 (15)	C23—C24—C25	106.4 (2)
O1—C1—N1	129.82 (17)	C23—C24—H24	126.8
O1—C1—C3	116.43 (17)	C25—C24—H24	126.8
N1—C1—C3	113.68 (16)	C26—C25—C24	106.6 (2)
N1—C2—N2	116.65 (16)	C26—C25—H25	126.7
N1—C2—S1	126.82 (15)	C24—C25—H25	126.7
N2—C2—S1	116.34 (13)	C25—C26—O4	110.9 (2)
C4—C3—O3	109.47 (17)	C25—C26—H26	124.5
C4—C3—C1	133.14 (19)	O4—C26—H26	124.5
O3—C3—C1	117.37 (16)	N4—C27—C28	112.38 (16)
C3—C4—C5	106.6 (2)	N4—C27—H27A	109.1
C3—C4—H4	126.7	C28—C27—H27A	109.1
C5—C4—H4	126.7	N4—C27—H27B	109.1
C6—C5—C4	106.7 (2)	C28—C27—H27B	109.1
C6—C5—H5	126.6	H27A—C27—H27B	107.9
C4—C5—H5	126.6	C29—C28—C33	118.8 (2)
C5—C6—O3	110.8 (2)	C29—C28—C27	120.63 (19)
C5—C6—H6	124.6	C33—C28—C27	120.6 (2)
O3—C6—H6	124.6	C28—C29—C30	120.7 (2)
N2—C7—C8	115.16 (15)	C28—C29—H29	119.7
N2—C7—H7A	108.5	C30—C29—H29	119.7
C8—C7—H7A	108.5	C31—C30—C29	120.4 (3)
N2—C7—H7B	108.5	C31—C30—H30	119.8
C8—C7—H7B	108.5	C29—C30—H30	119.8
H7A—C7—H7B	107.5	C32—C31—C30	119.8 (3)
C9—C8—C13	118.95 (18)	C32—C31—H31	120.1
C9—C8—C7	120.94 (17)	C30—C31—H31	120.1
C13—C8—C7	119.98 (17)	C31—C32—C33	120.3 (3)
C10—C9—C8	120.9 (2)	C31—C32—H32	119.8
C10—C9—H9	119.5	C33—C32—H32	119.8
C8—C9—H9	119.5	C28—C33—C32	120.1 (3)
C9—C10—C11	119.6 (2)	C28—C33—H33	119.9
C9—C10—H10	120.2	C32—C33—H33	119.9
C11—C10—H10	120.2	N4—C34—C35	112.60 (16)
C12—C11—C10	120.2 (2)	N4—C34—H34A	109.1
C12—C11—H11	119.9	C35—C34—H34A	109.1
C10—C11—H11	119.9	N4—C34—H34B	109.1
C11—C12—C13	119.9 (2)	C35—C34—H34B	109.1
C11—C12—H12	120.1	H34A—C34—H34B	107.8
C13—C12—H12	120.1	C40—C35—C36	118.4 (2)
C8—C13—C12	120.4 (2)	C40—C35—C34	120.16 (19)
C8—C13—H13	119.8	C36—C35—C34	121.42 (18)
C12—C13—H13	119.8	C37—C36—C35	120.4 (2)
N2—C14—C15	114.88 (16)	C37—C36—H36	119.8
N2—C14—H14A	108.5	C35—C36—H36	119.8
C15—C14—H14A	108.5	C38—C37—C36	120.4 (3)
N2—C14—H14B	108.5	C38—C37—H37	119.8
C15—C14—H14B	108.5	C36—C37—H37	119.8
H14A—C14—H14B	107.5	C39—C38—C37	119.6 (3)
C16—C15—C20	118.4 (2)	C39—C38—H38	120.2
C16—C15—C14	123.75 (18)	C37—C38—H38	120.2
C20—C15—C14	117.8 (2)	C38—C39—C40	120.3 (2)
C15—C16—C17	120.5 (2)	C38—C39—H39	119.9
C15—C16—H16	119.7	C40—C39—H39	119.9
C17—C16—H16	119.7	C39—C40—C35	120.9 (2)
C18—C17—C16	120.0 (3)	C39—C40—H40	119.5
C18—C17—H17	120	C35—C40—H40	119.5
O1—Ni—S1—C2	−13.85 (8)	C16—C17—C18—C19	0.4 (4)
S2—Ni—S1—C2	176.58 (7)	C17—C18—C19—C20	0.2 (4)
O2—Ni—S2—C22	−10.43 (9)	C18—C19—C20—C15	−0.4 (4)
O1—Ni—S2—C22	90.0 (3)	C16—C15—C20—C19	−0.1 (3)
S1—Ni—S2—C22	179.46 (7)	C14—C15—C20—C19	−179.9 (2)
O2—Ni—O1—C1	−173.40 (18)	Ni—O2—C21—N3	17.7 (3)
S1—Ni—O1—C1	−3.21 (17)	Ni—O2—C21—C23	−166.36 (15)
S2—Ni—O1—C1	85.4 (3)	C22—N3—C21—O2	−8.0 (3)
O1—Ni—O2—C21	−174.92 (19)	C22—N3—C21—C23	175.98 (18)
S2—Ni—O2—C21	−5.16 (19)	C21—N3—C22—N4	169.86 (18)
Ni—O1—C1—N1	19.1 (3)	C21—N3—C22—S2	−14.4 (3)
Ni—O1—C1—C3	−164.31 (13)	C34—N4—C22—N3	177.04 (17)
C2—N1—C1—O1	−10.8 (3)	C27—N4—C22—N3	−2.3 (3)
C2—N1—C1—C3	172.54 (16)	C34—N4—C22—S2	0.8 (3)
C1—N1—C2—N2	170.64 (17)	C27—N4—C22—S2	−178.49 (14)
C1—N1—C2—S1	−14.5 (3)	Ni—S2—C22—N3	21.39 (19)
C14—N2—C2—N1	−179.94 (16)	Ni—S2—C22—N4	−162.87 (13)
C7—N2—C2—N1	5.6 (3)	C26—O4—C23—C24	−0.3 (3)
C14—N2—C2—S1	4.7 (2)	C26—O4—C23—C21	−177.2 (2)
C7—N2—C2—S1	−169.83 (13)	O2—C21—C23—C24	−171.6 (2)
Ni—S1—C2—N1	24.97 (18)	N3—C21—C23—C24	5.1 (3)
Ni—S1—C2—N2	−160.18 (12)	O2—C21—C23—O4	4.6 (3)
C6—O3—C3—C4	0.4 (2)	N3—C21—C23—O4	−178.80 (18)
C6—O3—C3—C1	179.04 (18)	O4—C23—C24—C25	0.3 (3)
O1—C1—C3—C4	−176.7 (2)	C21—C23—C24—C25	176.7 (2)
N1—C1—C3—C4	0.5 (3)	C23—C24—C25—C26	−0.2 (3)
O1—C1—C3—O3	5.1 (3)	C24—C25—C26—O4	0.0 (4)
N1—C1—C3—O3	−177.75 (17)	C23—O4—C26—C25	0.2 (3)
O3—C3—C4—C5	−0.7 (3)	C22—N4—C27—C28	102.7 (2)
C1—C3—C4—C5	−179.0 (2)	C34—N4—C27—C28	−76.7 (2)
C3—C4—C5—C6	0.7 (3)	N4—C27—C28—C29	−58.2 (3)
C4—C5—C6—O3	−0.4 (3)	N4—C27—C28—C33	124.0 (2)
C3—O3—C6—C5	0.0 (3)	C33—C28—C29—C30	−0.7 (4)
C2—N2—C7—C8	−107.9 (2)	C27—C28—C29—C30	−178.5 (3)
C14—N2—C7—C8	77.1 (2)	C28—C29—C30—C31	1.0 (5)
N2—C7—C8—C9	71.4 (2)	C29—C30—C31—C32	−0.6 (5)
N2—C7—C8—C13	−112.9 (2)	C30—C31—C32—C33	−0.1 (5)
C13—C8—C9—C10	−0.8 (3)	C29—C28—C33—C32	0.0 (4)
C7—C8—C9—C10	175.0 (2)	C27—C28—C33—C32	177.8 (2)
C8—C9—C10—C11	0.0 (4)	C31—C32—C33—C28	0.4 (4)
C9—C10—C11—C12	0.8 (4)	C22—N4—C34—C35	101.7 (2)
C10—C11—C12—C13	−0.7 (4)	C27—N4—C34—C35	−78.9 (2)
C9—C8—C13—C12	0.8 (3)	N4—C34—C35—C40	110.8 (2)
C7—C8—C13—C12	−175.0 (2)	N4—C34—C35—C36	−69.8 (2)
C11—C12—C13—C8	−0.1 (4)	C40—C35—C36—C37	−0.3 (3)
C2—N2—C14—C15	−87.8 (2)	C34—C35—C36—C37	−179.7 (2)
C7—N2—C14—C15	87.0 (2)	C35—C36—C37—C38	0.1 (4)
N2—C14—C15—C16	8.0 (3)	C36—C37—C38—C39	−0.1 (4)
N2—C14—C15—C20	−172.23 (18)	C37—C38—C39—C40	0.3 (4)
C20—C15—C16—C17	0.8 (3)	C38—C39—C40—C35	−0.6 (4)
C14—C15—C16—C17	−179.4 (2)	C36—C35—C40—C39	0.6 (4)
C15—C16—C17—C18	−1.0 (4)	C34—C35—C40—C39	180.0 (2)

Table 1

Selected bond lengths (Å)

Ni—O2	1.8645 (14)
Ni—O1	1.8664 (13)
Ni—S1	2.1392 (6)
Ni—S2	2.1444 (5)