Dichloro­bis[(S)-2,3,5,6-tetra­hydro-6-phenyl­imidazo[2,1-b]thia­zole]nickel(II)

The title compound, [NiCl₂(C₁₁H₁₂N₂S)₂], crystallizes with two independent mol­ecules per asymmetric unit. The Ni atom displays a pseudo-tetra­hedral environment of the ligands, as expected for paramagnetic Ni^II compounds.

Key indicators

• Single-crystal X-ray study
• T = 200 K
• Mean [sigma](C-C) = 0.017 Å
• Disorder in main residue
• R factor = 0.075
• wR factor = 0.245
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          1
PLAT341_ALERT_3_B Low Bond Precision on C-C bonds (x 1000) Ang ...         17

Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C59
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for       C200
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C50B
PLAT301_ALERT_3_C Main Residue  Disorder .........................       2.00 Perc.
PLAT322_ALERT_2_C Check Hybridisation of  S7     in Main Residue .          ?
PLAT431_ALERT_2_C Short Inter HL..A Contact  Cl4    ..  S8      ..       3.40 Ang.

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           69.55
           From the CIF: _reflns_number_total               7693
           Count of symmetry unique reflns         4763
           Completeness (_total/calc)            161.52%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      2930
           Fraction of Friedel pairs measured     0.615
           Are heavy atom types Z>Si present        yes

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

Levamisole (lvms), (-)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole, and levamisole hydrochloride are well known anthelmintic drugs with immunomodulatory (Amery & Bruynseels, 1992) and anticancer (Kovach et al., 1992) activities. However, very few inorganic derivatives of levamisole have been reported. The only examples to date are the mononuclear complexes [MCl₂(lvms)₂] (M = Co, Ni, Cu or Zn; Kovachev et al., 1994), [Pd(η²-aminoacidato)(lvms)₂]Cl (Nijasure et al., 1999) and [PtCl(en)(lvms)]Cl (en is ?; Arvanitis et al., 1993). A trinuclear derivative, [Ru₃(µ-Cl)(µ-η²-C₁₁H₁₃N₂S—C,S)(CO)₉], was also reported by Cabeza et al. (2002). The ligand of the latter complex arises from a C—S bond cleavage of levamisole hydrochloride. To date, only the structures of the last two complexes have been determined by X-ray diffraction methods. We report here the structure of the title compound, (I), a compound previously described by the Stoychkov group (Kovachev et al., 1994), which has some activity as an immunomodulating drug.

The structure of one of the independent chiral molecules of [NiCl₂(lvms)₂], (I), is illustrated in Fig. 1. The compound crystallizes in the monoclinic space group P2₁, with two independent molecules in the asymmetric unit. The coordination environment of the Ni atom is nearly tetrahedral. Both levamisole ligands bind to the metal atom through their sp²-hybridized N atom.

S2. Experimental

Compound (I) was synthesized as previously described by Kovachev et al. (1994). Crystallization was accomplished from an acetone–diethyl ether solution (Ratio?) at room temperature by slow liquid–liquid diffusion.

S3. Refinement

All H atoms were placed in calculated positions, with C—H distances in the range 0.93–0.98 Å. They were included in the refinement in a riding-motion approximation, with U_iso(H) = 1.2U_eq of the carrier atom. Atom C50 was found to be disordered between two alternative sites, C50A and C50B, with occupancies of 70% and 30%, respectively. The split atomic positions for C50 were refined isotropically.

Computing details

Data collection: COLLECT (Nonius, 1997–2000); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK and DENZO (Otwinowski & Minor, 1997); program(s) used to solve structure: DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

Figures

Fig. 1. The molecular structure of one of the independent molecules of (I), showing 50% probability displacement ellipsoids.

Dichlorobis[(-)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole]nickel(II)

Crystal data

[NiCl2(C11H12N2S)2]	F(000) = 1112
Mr = 538.19	Dx = 1.497 Mg m^−3
Monoclinic, P21	Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2yb	Cell parameters from 4366 reflections
a = 8.1791 (5) Å	θ = 1.4–69.6°
b = 9.2534 (4) Å	µ = 5.00 mm^−1
c = 31.556 (2) Å	T = 200 K
β = 91.637 (3)°	Plate, blue
V = 2387.3 (2) Å^3	0.18 × 0.18 × 0.03 mm
Z = 4

Data collection

Nonius KappaCCD area-detector diffractometer	7693 independent reflections
Radiation source: fine-focus sealed tube	6015 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromator	Rint = 0.061
Detector resolution: 9 pixels mm^-1	θmax = 69.6°, θmin = 1.4°
ϕ and ω scans	h = −9→9
Absorption correction: part of the refinement model (ΔF) (Parkin et al., 1995)	k = −11→9
Tmin = 0.476, Tmax = 0.866	l = −38→38
7693 measured reflections

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.076	w = 1/[σ^2(Fo^2) + (0.1088P)^2 + 6.3761P] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.245	(Δ/σ)max = 0.001
S = 1.18	Δρmax = 0.91 e Å^−3
7693 reflections	Δρmin = −0.77 e Å^−3
559 parameters	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0016 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), with how many Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: 0.02 (4)

Special details

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl4	0.4849 (3)	0.8049 (4)	0.96554 (8)	0.0704 (9)
Cl3	0.1901 (4)	0.5214 (4)	0.66709 (10)	0.0695 (8)
N2	0.4176 (10)	0.6293 (11)	0.8737 (2)	0.050 (2)
N1	0.5049 (11)	0.5507 (10)	0.5956 (2)	0.051 (2)
N3	0.5070 (10)	0.3117 (10)	0.6593 (2)	0.050 (2)
N4	0.1232 (10)	0.6740 (10)	0.9290 (2)	0.048 (2)
C1	0.4793 (13)	0.2738 (14)	0.7037 (3)	0.056 (3)
H1	0.4248	0.3539	0.7179	0.067*
S7	0.7609 (4)	0.2696 (4)	0.60556 (9)	0.0707 (8)
S5	0.1843 (4)	0.6307 (4)	1.01441 (9)	0.0746 (9)
C25	0.0194 (16)	0.5121 (17)	0.7882 (4)	0.074 (4)
H25	0.0168	0.5473	0.7606	0.089*
C22	0.0348 (13)	0.4074 (14)	0.8699 (4)	0.065 (3)
H22	0.0434	0.3706	0.8973	0.078*
N10	0.7118 (10)	0.7118 (10)	0.5879 (2)	0.051 (2)
C23	0.0011 (12)	0.5518 (12)	0.8641 (3)	0.049 (2)
C26	0.0471 (16)	0.3659 (17)	0.7958 (4)	0.077 (4)
H26	0.0593	0.3026	0.7732	0.092*
C24	−0.0042 (13)	0.6046 (15)	0.8218 (3)	0.060 (3)
H24	−0.0238	0.7021	0.8167	0.072*
C11	−0.0285 (10)	0.6563 (12)	0.8994 (3)	0.045 (2)
H11	−0.0601	0.7505	0.8876	0.054*
C21	−0.1638 (14)	0.6014 (19)	0.9291 (4)	0.078 (4)
H21A	−0.2462	0.6750	0.9333	0.094*
H21B	−0.2161	0.5150	0.9178	0.094*
N7	−0.0740 (14)	0.5709 (15)	0.9680 (3)	0.084 (4)
C10	0.0807 (15)	0.6287 (14)	0.9661 (3)	0.060 (3)
C33	0.6569 (12)	0.2556 (15)	0.7224 (3)	0.057 (3)
H33A	0.7016	0.3465	0.7328	0.068*
H33B	0.6621	0.1844	0.7450	0.068*
C36	0.3534 (14)	0.0412 (14)	0.6742 (3)	0.061 (3)
H36	0.3904	0.0651	0.6475	0.074*
N6	0.7383 (11)	0.2063 (10)	0.6852 (3)	0.055 (2)
C34	0.3793 (12)	0.1362 (13)	0.7080 (3)	0.051 (2)
C32	0.6522 (12)	0.2629 (13)	0.6513 (3)	0.052 (2)
C35	0.3178 (14)	0.0969 (14)	0.7473 (3)	0.059 (3)
H35	0.3316	0.1588	0.7703	0.071*
C30	0.9366 (17)	0.1848 (17)	0.6334 (5)	0.084 (4)
H30A	0.9395	0.0821	0.6274	0.100*
H30B	1.0380	0.2279	0.6244	0.100*
C31	0.9150 (13)	0.2101 (18)	0.6804 (4)	0.075 (4)
H31A	0.9683	0.1348	0.6971	0.090*
H31B	0.9595	0.3031	0.6890	0.090*
C77	0.4486 (13)	0.6427 (12)	0.8274 (3)	0.047 (2)
H77	0.3451	0.6618	0.8120	0.057*
C58	0.2750 (14)	−0.0854 (15)	0.6800 (3)	0.062 (3)
H58	0.2608	−0.1487	0.6573	0.074*
C56	0.2372 (14)	−0.0320 (15)	0.7522 (4)	0.065 (3)
H56	0.1977	−0.0567	0.7786	0.078*
C48	0.8361 (14)	0.7707 (16)	0.6542 (3)	0.065 (3)
H48A	0.7985	0.8689	0.6584	0.078*
H48B	0.9332	0.7545	0.6719	0.078*
C41	0.6832 (13)	0.6575 (14)	0.5453 (3)	0.055 (3)
H41A	0.7692	0.5915	0.5373	0.066*
H41B	0.6764	0.7359	0.5249	0.066*
C49	0.8724 (15)	0.7441 (16)	0.6072 (3)	0.068 (3)
H49A	0.9198	0.8293	0.5945	0.082*
H49B	0.9467	0.6633	0.6041	0.082*
C53	0.0561 (17)	0.3159 (15)	0.8361 (4)	0.078 (4)
H53	0.0771	0.2185	0.8410	0.094*
C42	0.5173 (12)	0.5783 (12)	0.5483 (3)	0.049 (2)
H42	0.5196	0.4867	0.5327	0.059*
C78	0.4394 (13)	0.4971 (14)	0.8839 (3)	0.054 (3)
C43	0.3734 (13)	0.6674 (11)	0.5338 (3)	0.048 (2)
C47	0.6199 (13)	0.6304 (12)	0.6139 (3)	0.048 (2)
C57	0.2150 (12)	−0.1227 (14)	0.7194 (4)	0.059 (3)
H57	0.1600	−0.2096	0.7229	0.071*
C45	0.2557 (13)	0.6109 (14)	0.5059 (3)	0.059 (3)
H45	0.2701	0.5180	0.4954	0.071*
C44	0.3461 (15)	0.8078 (13)	0.5484 (4)	0.061 (3)
H44	0.4214	0.8488	0.5675	0.074*
C51	−0.1346 (16)	0.561 (2)	1.0103 (4)	0.086 (5)
H51A	−0.2325	0.6196	1.0120	0.104*
H51B	−0.1652	0.4616	1.0158	0.104*
C50A	0.034 (2)	0.522 (3)	1.0381 (6)	0.076 (5)*	0.70
H50A	0.0606	0.4202	1.0359	0.091*	0.70
H50B	0.0227	0.5467	1.0678	0.091*	0.70
N55	0.4826 (14)	0.4055 (14)	0.8521 (3)	0.080 (3)
C65	0.1147 (14)	0.6895 (16)	0.4930 (4)	0.064 (3)
H65	0.0362	0.6478	0.4749	0.076*
C66	0.0954 (16)	0.8263 (15)	0.5072 (4)	0.065 (3)
H66	0.0047	0.8794	0.4980	0.078*
C59	0.5101 (17)	0.4911 (17)	0.8158 (4)	0.080 (4)
H59A	0.4497	0.4534	0.7913	0.097*
H59B	0.6255	0.4934	0.8095	0.097*
C67	0.2091 (16)	0.8888 (15)	0.5352 (4)	0.071 (3)
H67	0.1944	0.9825	0.5451	0.085*
C99	0.5691 (12)	0.7596 (13)	0.8176 (3)	0.051 (2)
C104	0.6034 (14)	0.7827 (14)	0.7749 (3)	0.059 (3)
H104	0.5499	0.7286	0.7539	0.071*
C101	0.7635 (14)	0.9500 (12)	0.8363 (3)	0.056 (3)
H101	0.8164	1.0058	0.8570	0.068*
C100	0.6480 (14)	0.8454 (13)	0.8481 (3)	0.056 (3)
H100	0.6243	0.8335	0.8765	0.067*
C103	0.7976 (14)	0.9695 (14)	0.7950 (4)	0.064 (3)
H103	0.8744	1.0381	0.7872	0.077*
C102	0.7164 (16)	0.8856 (16)	0.7640 (4)	0.072 (4)
H102	0.7392	0.8997	0.7356	0.086*
S8	0.4305 (4)	0.4129 (4)	0.93304 (9)	0.0645 (7)
C201	0.5340 (17)	0.2628 (18)	0.8659 (6)	0.098 (5)
H20A	0.6525	0.2569	0.8672	0.118*
H20B	0.4926	0.1902	0.8462	0.118*
C200	0.466 (2)	0.2379 (18)	0.9095 (6)	0.104 (6)
H20C	0.5431	0.1830	0.9270	0.125*
H20D	0.3643	0.1840	0.9072	0.125*
C50B	−0.039 (5)	0.599 (5)	1.0373 (11)	0.056 (9)*	0.30
H50C	−0.0321	0.5265	1.0595	0.067*	0.30
H50D	−0.0766	0.6883	1.0498	0.067*	0.30
Ni1	0.31525 (19)	0.7756 (2)	0.91004 (5)	0.0483 (5)
Cl2	0.2100 (4)	0.9477 (3)	0.86709 (8)	0.0633 (7)
Ni2	0.3531 (2)	0.4157 (2)	0.62077 (5)	0.0508 (5)
S1	0.6777 (4)	0.6425 (4)	0.66674 (8)	0.0611 (8)
Cl1	0.2914 (4)	0.2683 (4)	0.56682 (8)	0.0732 (9)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl4	0.0603 (15)	0.093 (3)	0.0572 (14)	0.0024 (16)	−0.0005 (11)	−0.0216 (15)
Cl3	0.0699 (18)	0.0561 (19)	0.0829 (19)	0.0054 (15)	0.0116 (14)	−0.0035 (15)
N2	0.055 (5)	0.050 (6)	0.045 (4)	−0.007 (4)	−0.002 (3)	0.000 (4)
N1	0.064 (5)	0.048 (6)	0.042 (4)	0.008 (4)	0.000 (4)	0.005 (4)
N3	0.051 (5)	0.055 (6)	0.044 (4)	−0.006 (4)	0.000 (3)	−0.003 (4)
N4	0.048 (5)	0.047 (6)	0.048 (4)	0.003 (4)	0.001 (3)	−0.004 (4)
C1	0.071 (6)	0.060 (7)	0.038 (4)	−0.008 (6)	0.005 (4)	−0.003 (5)
S7	0.0730 (18)	0.072 (2)	0.0679 (16)	−0.0005 (18)	0.0211 (14)	0.0014 (16)
S5	0.094 (2)	0.082 (3)	0.0477 (14)	−0.013 (2)	−0.0014 (13)	0.0081 (14)
C25	0.071 (8)	0.084 (11)	0.066 (7)	−0.018 (8)	−0.004 (6)	−0.019 (7)
C22	0.048 (6)	0.048 (7)	0.097 (8)	−0.007 (6)	−0.021 (5)	0.023 (7)
N10	0.052 (5)	0.057 (6)	0.044 (4)	−0.012 (4)	−0.004 (3)	0.002 (4)
C23	0.038 (5)	0.043 (7)	0.064 (6)	−0.015 (5)	−0.004 (4)	0.001 (5)
C26	0.065 (8)	0.074 (10)	0.090 (9)	0.011 (7)	−0.031 (7)	−0.019 (7)
C24	0.062 (7)	0.062 (8)	0.057 (6)	0.003 (6)	−0.001 (5)	0.000 (5)
C11	0.032 (5)	0.051 (7)	0.051 (5)	−0.003 (4)	0.001 (4)	0.006 (4)
C21	0.053 (7)	0.110 (13)	0.071 (7)	−0.001 (8)	0.003 (5)	−0.001 (7)
N7	0.074 (7)	0.117 (11)	0.063 (6)	−0.046 (7)	0.013 (5)	0.008 (6)
C10	0.076 (7)	0.063 (8)	0.040 (5)	−0.008 (7)	0.003 (5)	−0.005 (5)
C33	0.048 (5)	0.066 (8)	0.057 (5)	−0.013 (6)	−0.006 (4)	0.008 (5)
C36	0.072 (7)	0.061 (8)	0.052 (6)	−0.016 (6)	0.005 (5)	−0.003 (5)
N6	0.056 (5)	0.050 (6)	0.059 (5)	−0.005 (4)	0.003 (4)	0.002 (4)
C34	0.049 (5)	0.049 (7)	0.055 (5)	−0.008 (5)	0.007 (4)	0.001 (5)
C32	0.043 (5)	0.052 (7)	0.060 (5)	−0.021 (5)	0.006 (4)	−0.005 (5)
C35	0.071 (7)	0.055 (8)	0.052 (5)	0.004 (6)	0.014 (5)	0.002 (5)
C30	0.074 (9)	0.056 (9)	0.122 (12)	0.010 (7)	0.019 (8)	0.012 (8)
C31	0.035 (6)	0.096 (11)	0.094 (9)	−0.005 (6)	−0.001 (5)	0.005 (7)
C77	0.054 (6)	0.039 (6)	0.048 (5)	−0.011 (5)	0.009 (4)	−0.011 (4)
C58	0.072 (7)	0.057 (8)	0.058 (6)	−0.016 (7)	0.008 (5)	−0.001 (6)
C56	0.063 (7)	0.071 (9)	0.061 (6)	0.005 (6)	0.016 (5)	0.018 (6)
C48	0.066 (7)	0.070 (9)	0.060 (6)	−0.017 (7)	0.006 (5)	−0.004 (6)
C41	0.050 (6)	0.064 (8)	0.051 (5)	−0.015 (6)	0.000 (4)	0.001 (5)
C49	0.073 (7)	0.070 (9)	0.061 (6)	−0.010 (7)	0.002 (5)	0.002 (6)
C53	0.094 (10)	0.044 (8)	0.095 (9)	0.015 (7)	−0.037 (8)	−0.003 (7)
C42	0.057 (6)	0.047 (6)	0.044 (5)	−0.011 (5)	−0.001 (4)	0.007 (4)
C78	0.049 (6)	0.059 (8)	0.053 (5)	0.003 (5)	−0.012 (4)	−0.009 (5)
C43	0.057 (6)	0.039 (6)	0.047 (5)	0.004 (5)	−0.002 (4)	0.004 (4)
C47	0.059 (6)	0.036 (6)	0.049 (5)	−0.008 (5)	0.007 (4)	0.008 (4)
C57	0.044 (6)	0.060 (8)	0.075 (7)	−0.019 (5)	0.001 (5)	0.007 (6)
C45	0.058 (7)	0.053 (7)	0.067 (6)	−0.002 (6)	0.005 (5)	−0.003 (5)
C44	0.076 (7)	0.040 (7)	0.068 (6)	0.000 (6)	0.000 (5)	0.002 (5)
C51	0.067 (8)	0.134 (15)	0.059 (7)	−0.035 (9)	0.017 (6)	0.004 (8)
N55	0.099 (8)	0.072 (8)	0.066 (6)	0.021 (7)	−0.026 (5)	−0.030 (6)
C65	0.049 (6)	0.076 (10)	0.066 (7)	0.008 (6)	0.004 (5)	0.013 (6)
C66	0.071 (8)	0.055 (8)	0.068 (7)	−0.003 (6)	0.003 (6)	0.021 (6)
C59	0.078 (8)	0.091 (11)	0.075 (8)	−0.028 (8)	0.034 (7)	−0.021 (7)
C67	0.079 (8)	0.050 (8)	0.083 (8)	0.021 (7)	0.014 (6)	0.004 (6)
C99	0.048 (5)	0.055 (7)	0.051 (5)	0.002 (5)	0.011 (4)	−0.007 (5)
C104	0.078 (7)	0.058 (7)	0.043 (5)	0.000 (7)	0.013 (5)	0.002 (5)
C101	0.065 (6)	0.040 (7)	0.064 (6)	0.005 (5)	0.012 (5)	−0.008 (5)
C100	0.064 (7)	0.058 (8)	0.045 (5)	0.010 (6)	0.002 (4)	−0.005 (5)
C103	0.053 (6)	0.056 (8)	0.084 (8)	−0.016 (6)	0.012 (6)	−0.001 (6)
C102	0.088 (9)	0.071 (10)	0.057 (6)	−0.005 (7)	0.012 (6)	0.010 (6)
S8	0.0700 (17)	0.0515 (18)	0.0712 (16)	0.0025 (16)	−0.0093 (13)	0.0050 (14)
C201	0.062 (8)	0.053 (9)	0.180 (17)	0.013 (7)	0.022 (9)	−0.007 (10)
C200	0.132 (14)	0.060 (11)	0.118 (13)	0.029 (10)	−0.035 (11)	−0.019 (9)
Ni1	0.0515 (9)	0.0486 (11)	0.0452 (8)	0.0012 (9)	0.0070 (6)	−0.0033 (8)
Cl2	0.0724 (17)	0.0579 (19)	0.0596 (14)	0.0068 (15)	0.0034 (12)	0.0058 (12)
Ni2	0.0546 (10)	0.0503 (11)	0.0472 (8)	−0.0080 (9)	−0.0029 (7)	0.0030 (8)
S1	0.0718 (18)	0.065 (2)	0.0458 (13)	−0.0168 (16)	−0.0025 (11)	−0.0016 (12)
Cl1	0.097 (2)	0.072 (2)	0.0507 (13)	−0.0274 (19)	−0.0063 (13)	−0.0048 (14)

Geometric parameters (Å, º)

Cl4—Ni1	2.220 (3)	C58—C57	1.391 (14)
Cl3—Ni2	2.232 (3)	C58—H58	0.9300
N2—C78	1.276 (15)	C56—C57	1.342 (17)
N2—C77	1.497 (11)	C56—H56	0.9300
N2—Ni1	1.975 (9)	C48—C49	1.541 (15)
N1—C47	1.316 (13)	C48—S1	1.808 (12)
N1—C42	1.521 (11)	C48—H48A	0.9700
N1—Ni2	1.946 (9)	C48—H48B	0.9700
N3—C32	1.302 (13)	C41—C42	1.548 (14)
N3—C1	1.471 (11)	C41—H41A	0.9700
N3—Ni2	1.974 (9)	C41—H41B	0.9700
N4—C10	1.300 (13)	C49—H49A	0.9700
N4—C11	1.540 (12)	C49—H49B	0.9700
N4—Ni1	1.940 (8)	C53—H53	0.9300
C1—C34	1.521 (16)	C42—C43	1.497 (14)
C1—C33	1.561 (14)	C42—H42	0.9800
C1—H1	0.9800	C78—N55	1.369 (14)
S7—C32	1.719 (10)	C78—S8	1.737 (12)
S7—C30	1.839 (14)	C43—C45	1.389 (15)
S5—C10	1.722 (11)	C43—C44	1.398 (15)
S5—C50A	1.77 (2)	C47—S1	1.723 (10)
S5—C50B	2.00 (4)	C57—H57	0.9300
C25—C24	1.381 (17)	C45—C65	1.414 (16)
C25—C26	1.39 (2)	C45—H45	0.9300
C25—H25	0.9300	C44—C67	1.401 (16)
C22—C23	1.376 (17)	C44—H44	0.9300
C22—C53	1.377 (18)	C51—C50B	1.20 (4)
C22—H22	0.9300	C51—C50A	1.65 (2)
N10—C47	1.357 (12)	C51—H51A	0.9700
N10—C41	1.447 (12)	C51—H51B	0.9700
N10—C49	1.463 (14)	C50A—H50A	0.9700
C23—C24	1.420 (14)	C50A—H50B	0.9700
C23—C11	1.502 (14)	N55—C59	1.417 (18)
C26—C53	1.351 (19)	N55—C201	1.449 (19)
C26—H26	0.9300	C65—C66	1.353 (18)
C24—H24	0.9300	C65—H65	0.9300
C11—C21	1.555 (15)	C66—C67	1.392 (18)
C11—H11	0.9800	C66—H66	0.9300
C21—N7	1.439 (16)	C59—H59A	0.9700
C21—H21A	0.9700	C59—H59B	0.9700
C21—H21B	0.9700	C67—H67	0.9300
N7—C10	1.377 (15)	C99—C100	1.393 (15)
N7—C51	1.442 (14)	C99—C104	1.400 (13)
C33—N6	1.441 (14)	C104—C102	1.378 (17)
C33—H33A	0.9700	C104—H104	0.9300
C33—H33B	0.9700	C101—C103	1.353 (15)
C36—C58	1.351 (17)	C101—C100	1.410 (16)
C36—C34	1.392 (15)	C101—H101	0.9300
C36—H36	0.9300	C100—H100	0.9300
N6—C32	1.366 (14)	C103—C102	1.401 (17)
N6—C31	1.458 (14)	C103—H103	0.9300
C34—C35	1.400 (14)	C102—H102	0.9300
C35—C56	1.374 (17)	S8—C200	1.808 (16)
C35—H35	0.9300	C201—C200	1.52 (2)
C30—C31	1.514 (19)	C201—H20A	0.9700
C30—H30A	0.9700	C201—H20B	0.9700
C30—H30B	0.9700	C200—H20C	0.9700
C31—H31A	0.9700	C200—H20D	0.9700
C31—H31B	0.9700	C50B—H50C	0.9700
C77—C99	1.502 (15)	C50B—H50D	0.9700
C77—C59	1.538 (18)	Ni1—Cl2	2.247 (3)
C77—H77	0.9800	Ni2—Cl1	2.228 (3)
C78—N2—C77	107.5 (9)	N10—C49—H49A	111.0
C78—N2—Ni1	124.7 (7)	C48—C49—H49A	111.0
C77—N2—Ni1	126.6 (7)	N10—C49—H49B	111.0
C47—N1—C42	105.7 (8)	C48—C49—H49B	111.0
C47—N1—Ni2	129.6 (7)	H49A—C49—H49B	109.0
C42—N1—Ni2	124.7 (7)	C26—C53—C22	120.9 (13)
C32—N3—C1	105.4 (8)	C26—C53—H53	119.6
C32—N3—Ni2	128.3 (7)	C22—C53—H53	119.6
C1—N3—Ni2	126.2 (7)	C43—C42—N1	108.5 (8)
C10—N4—C11	106.3 (8)	C43—C42—C41	113.8 (9)
C10—N4—Ni1	132.3 (8)	N1—C42—C41	102.8 (7)
C11—N4—Ni1	120.7 (6)	C43—C42—H42	110.5
N3—C1—C34	112.4 (8)	N1—C42—H42	110.5
N3—C1—C33	102.7 (8)	C41—C42—H42	110.5
C34—C1—C33	111.9 (10)	N2—C78—N55	116.4 (11)
N3—C1—H1	109.9	N2—C78—S8	130.2 (8)
C34—C1—H1	109.9	N55—C78—S8	113.3 (10)
C33—C1—H1	109.9	C45—C43—C44	116.3 (10)
C32—S7—C30	89.9 (6)	C45—C43—C42	120.7 (10)
C10—S5—C50A	92.1 (8)	C44—C43—C42	122.9 (10)
C10—S5—C50B	83.6 (11)	N1—C47—N10	116.5 (9)
C24—C25—C26	119.7 (14)	N1—C47—S1	129.3 (7)
C24—C25—H25	120.2	N10—C47—S1	114.1 (8)
C26—C25—H25	120.2	C56—C57—C58	119.4 (11)
C23—C22—C53	121.5 (12)	C56—C57—H57	120.3
C23—C22—H22	119.2	C58—C57—H57	120.3
C53—C22—H22	119.2	C43—C45—C65	122.3 (12)
C47—N10—C41	107.0 (8)	C43—C45—H45	118.9
C47—N10—C49	111.5 (8)	C65—C45—H45	118.9
C41—N10—C49	125.2 (9)	C43—C44—C67	122.3 (12)
C22—C23—C24	117.4 (11)	C43—C44—H44	118.9
C22—C23—C11	124.2 (10)	C67—C44—H44	118.9
C24—C23—C11	118.4 (10)	C50B—C51—N7	114 (2)
C53—C26—C25	120.0 (13)	N7—C51—C50A	101.6 (11)
C53—C26—H26	120.0	C50B—C51—H51A	108.8
C25—C26—H26	120.0	N7—C51—H51A	108.8
C25—C24—C23	120.5 (13)	C50A—C51—H51A	140.4
C25—C24—H24	119.7	C50B—C51—H51B	108.8
C23—C24—H24	119.7	N7—C51—H51B	108.8
C23—C11—N4	112.0 (8)	C50A—C51—H51B	85.1
C23—C11—C21	111.7 (10)	H51A—C51—H51B	107.7
N4—C11—C21	104.1 (8)	C51—C50A—S5	103.4 (12)
C23—C11—H11	109.6	C51—C50A—H50A	111.1
N4—C11—H11	109.6	S5—C50A—H50A	111.1
C21—C11—H11	109.6	C51—C50A—H50B	111.1
N7—C21—C11	102.9 (9)	S5—C50A—H50B	111.1
N7—C21—H21A	111.2	H50A—C50A—H50B	109.1
C11—C21—H21A	111.2	C78—N55—C59	107.4 (12)
N7—C21—H21B	111.2	C78—N55—C201	115.0 (12)
C11—C21—H21B	111.2	C59—N55—C201	134.5 (12)
H21A—C21—H21B	109.1	C66—C65—C45	119.2 (12)
C10—N7—C21	109.6 (10)	C66—C65—H65	120.4
C10—N7—C51	113.9 (10)	C45—C65—H65	120.4
C21—N7—C51	128.4 (11)	C65—C66—C67	121.2 (13)
N4—C10—N7	115.7 (10)	C65—C66—H66	119.4
N4—C10—S5	131.0 (9)	C67—C66—H66	119.4
N7—C10—S5	113.3 (8)	N55—C59—C77	104.9 (9)
N6—C33—C1	99.9 (8)	N55—C59—H59A	110.8
N6—C33—H33A	111.8	C77—C59—H59A	110.8
C1—C33—H33A	111.8	N55—C59—H59B	110.8
N6—C33—H33B	111.8	C77—C59—H59B	110.8
C1—C33—H33B	111.8	H59A—C59—H59B	108.8
H33A—C33—H33B	109.5	C66—C67—C44	118.7 (12)
C58—C36—C34	120.5 (10)	C66—C67—H67	120.7
C58—C36—H36	119.8	C44—C67—H67	120.7
C34—C36—H36	119.8	C100—C99—C104	118.5 (11)
C32—N6—C33	106.1 (9)	C100—C99—C77	124.2 (9)
C32—N6—C31	113.5 (9)	C104—C99—C77	117.3 (10)
C33—N6—C31	124.0 (9)	C102—C104—C99	119.9 (11)
C36—C34—C35	117.6 (11)	C102—C104—H104	120.0
C36—C34—C1	122.2 (9)	C99—C104—H104	120.0
C35—C34—C1	120.2 (10)	C103—C101—C100	120.3 (11)
N3—C32—N6	115.8 (9)	C103—C101—H101	119.8
N3—C32—S7	130.2 (9)	C100—C101—H101	119.8
N6—C32—S7	113.8 (8)	C99—C100—C101	120.6 (10)
C56—C35—C34	120.8 (11)	C99—C100—H100	119.7
C56—C35—H35	119.6	C101—C100—H100	119.7
C34—C35—H35	119.6	C101—C103—C102	119.4 (11)
C31—C30—S7	106.9 (9)	C101—C103—H103	120.3
C31—C30—H30A	110.3	C102—C103—H103	120.3
S7—C30—H30A	110.3	C104—C102—C103	121.2 (10)
C31—C30—H30B	110.3	C104—C102—H102	119.4
S7—C30—H30B	110.3	C103—C102—H102	119.4
H30A—C30—H30B	108.6	C78—S8—C200	91.4 (7)
N6—C31—C30	104.0 (10)	N55—C201—C200	107.5 (12)
N6—C31—H31A	111.0	N55—C201—H20A	110.2
C30—C31—H31A	111.0	C200—C201—H20A	110.2
N6—C31—H31B	111.0	N55—C201—H20B	110.2
C30—C31—H31B	111.0	C200—C201—H20B	110.2
H31A—C31—H31B	109.0	H20A—C201—H20B	108.5
N2—C77—C99	113.1 (8)	C201—C200—S8	107.7 (12)
N2—C77—C59	102.9 (9)	C201—C200—H20C	110.2
C99—C77—C59	112.8 (9)	S8—C200—H20C	110.2
N2—C77—H77	109.3	C201—C200—H20D	110.2
C99—C77—H77	109.3	S8—C200—H20D	110.2
C59—C77—H77	109.3	H20C—C200—H20D	108.5
C36—C58—C57	121.1 (11)	C51—C50B—S5	112 (2)
C36—C58—H58	119.5	C51—C50B—H50C	109.2
C57—C58—H58	119.5	S5—C50B—H50C	109.2
C57—C56—C35	120.6 (10)	C51—C50B—H50D	109.2
C57—C56—H56	119.7	S5—C50B—H50D	109.2
C35—C56—H56	119.7	H50C—C50B—H50D	107.9
C49—C48—S1	105.4 (9)	N4—Ni1—N2	102.0 (4)
C49—C48—H48A	110.7	N4—Ni1—Cl4	108.0 (2)
S1—C48—H48A	110.7	N2—Ni1—Cl4	106.0 (3)
C49—C48—H48B	110.7	N4—Ni1—Cl2	103.3 (3)
S1—C48—H48B	110.7	N2—Ni1—Cl2	107.3 (3)
H48A—C48—H48B	108.8	Cl4—Ni1—Cl2	127.53 (16)
N10—C41—C42	103.1 (8)	N1—Ni2—N3	99.3 (4)
N10—C41—H41A	111.1	N1—Ni2—Cl1	102.4 (3)
C42—C41—H41A	111.1	N3—Ni2—Cl1	107.3 (3)
N10—C41—H41B	111.1	N1—Ni2—Cl3	112.7 (3)
C42—C41—H41B	111.1	N3—Ni2—Cl3	101.1 (3)
H41A—C41—H41B	109.1	Cl1—Ni2—Cl3	129.95 (14)
N10—C49—C48	103.8 (9)	C47—S1—C48	90.5 (5)
C32—N3—C1—C34	−97.8 (10)	N1—C42—C43—C44	63.5 (13)
Ni2—N3—C1—C34	82.4 (12)	C41—C42—C43—C44	−50.3 (13)
C32—N3—C1—C33	22.7 (12)	C42—N1—C47—N10	0.7 (13)
Ni2—N3—C1—C33	−157.1 (8)	Ni2—N1—C47—N10	177.8 (8)
C53—C22—C23—C24	−2.6 (16)	C42—N1—C47—S1	−176.7 (9)
C53—C22—C23—C11	178.1 (10)	Ni2—N1—C47—S1	0.5 (16)
C24—C25—C26—C53	−2 (2)	C41—N10—C47—N1	−14.9 (13)
C26—C25—C24—C23	0.6 (19)	C49—N10—C47—N1	−155.2 (10)
C22—C23—C24—C25	1.7 (16)	C41—N10—C47—S1	162.8 (8)
C11—C23—C24—C25	−178.8 (10)	C49—N10—C47—S1	22.6 (12)
C22—C23—C11—N4	63.4 (13)	C35—C56—C57—C58	0.3 (18)
C24—C23—C11—N4	−116.0 (10)	C36—C58—C57—C56	−0.8 (19)
C22—C23—C11—C21	−53.0 (13)	C44—C43—C45—C65	−0.5 (16)
C24—C23—C11—C21	127.6 (10)	C42—C43—C45—C65	177.3 (10)
C10—N4—C11—C23	−117.4 (10)	C45—C43—C44—C67	−1.0 (16)
Ni1—N4—C11—C23	71.2 (10)	C42—C43—C44—C67	−178.7 (10)
C10—N4—C11—C21	3.5 (12)	C10—N7—C51—C50B	−3 (3)
Ni1—N4—C11—C21	−168.0 (8)	C21—N7—C51—C50B	−148 (3)
C23—C11—C21—N7	111.7 (12)	C10—N7—C51—C50A	−35.6 (19)
N4—C11—C21—N7	−9.3 (14)	C21—N7—C51—C50A	179.4 (16)
C11—C21—N7—C10	12.2 (16)	C50B—C51—C50A—S5	−77 (4)
C11—C21—N7—C51	158.4 (15)	N7—C51—C50A—S5	39.5 (16)
C11—N4—C10—N7	4.5 (15)	C10—S5—C50A—C51	−28.1 (13)
Ni1—N4—C10—N7	174.5 (9)	C50B—S5—C50A—C51	44 (2)
C11—N4—C10—S5	−174.4 (10)	N2—C78—N55—C59	6.8 (15)
Ni1—N4—C10—S5	−4.3 (19)	S8—C78—N55—C59	−171.0 (9)
C21—N7—C10—N4	−11.4 (17)	N2—C78—N55—C201	169.7 (11)
C51—N7—C10—N4	−162.9 (14)	S8—C78—N55—C201	−8.1 (15)
C21—N7—C10—S5	167.7 (11)	C43—C45—C65—C66	2.0 (17)
C51—N7—C10—S5	16.1 (17)	C45—C65—C66—C67	−2.1 (17)
C50A—S5—C10—N4	−171.2 (15)	C78—N55—C59—C77	−9.8 (13)
C50B—S5—C10—N4	162.5 (19)	C201—N55—C59—C77	−167.9 (14)
C50A—S5—C10—N7	9.9 (13)	N2—C77—C59—N55	9.4 (12)
C50B—S5—C10—N7	−16.4 (16)	C99—C77—C59—N55	131.5 (10)
N3—C1—C33—N6	−30.5 (11)	C65—C66—C67—C44	0.7 (18)
C34—C1—C33—N6	90.2 (10)	C43—C44—C67—C66	0.9 (18)
C1—C33—N6—C32	27.8 (11)	N2—C77—C99—C100	1.5 (15)
C1—C33—N6—C31	161.9 (11)	C59—C77—C99—C100	−114.7 (12)
C58—C36—C34—C35	−1.5 (18)	N2—C77—C99—C104	−178.6 (9)
C58—C36—C34—C1	174.8 (11)	C59—C77—C99—C104	65.2 (14)
N3—C1—C34—C36	14.6 (16)	C100—C99—C104—C102	1.8 (17)
C33—C1—C34—C36	−100.4 (12)	C77—C99—C104—C102	−178.1 (11)
N3—C1—C34—C35	−169.2 (10)	C104—C99—C100—C101	−1.9 (16)
C33—C1—C34—C35	75.8 (13)	C77—C99—C100—C101	178.0 (10)
C1—N3—C32—N6	−5.5 (13)	C103—C101—C100—C99	0.8 (17)
Ni2—N3—C32—N6	174.2 (7)	C100—C101—C103—C102	0.5 (18)
C1—N3—C32—S7	179.9 (9)	C99—C104—C102—C103	−1 (2)
Ni2—N3—C32—S7	−0.4 (16)	C101—C103—C102—C104	−1 (2)
C33—N6—C32—N3	−15.9 (13)	N2—C78—S8—C200	176.6 (12)
C31—N6—C32—N3	−155.4 (11)	N55—C78—S8—C200	−6.0 (11)
C33—N6—C32—S7	159.6 (8)	C78—N55—C201—C200	20.9 (18)
C31—N6—C32—S7	20.1 (13)	C59—N55—C201—C200	177.8 (15)
C30—S7—C32—N3	176.2 (12)	N55—C201—C200—S8	−23.7 (17)
C30—S7—C32—N6	1.5 (10)	C78—S8—C200—C201	17.1 (12)
C36—C34—C35—C56	1.0 (17)	N7—C51—C50B—S5	−10 (4)
C1—C34—C35—C56	−175.4 (11)	C50A—C51—C50B—S5	64 (3)
C32—S7—C30—C31	−21.0 (10)	C10—S5—C50B—C51	16 (3)
C32—N6—C31—C30	−34.9 (15)	C50A—S5—C50B—C51	−92 (4)
C33—N6—C31—C30	−166.0 (11)	C10—N4—Ni1—N2	113.7 (11)
S7—C30—C31—N6	33.6 (13)	C11—N4—Ni1—N2	−77.5 (7)
C78—N2—C77—C99	−127.7 (10)	C10—N4—Ni1—Cl4	2.2 (11)
Ni1—N2—C77—C99	64.6 (11)	C11—N4—Ni1—Cl4	171.1 (6)
C78—N2—C77—C59	−5.8 (11)	C10—N4—Ni1—Cl2	−135.1 (11)
Ni1—N2—C77—C59	−173.4 (7)	C11—N4—Ni1—Cl2	33.8 (7)
C34—C36—C58—C57	1.5 (19)	C78—N2—Ni1—N4	−46.7 (9)
C34—C35—C56—C57	−0.4 (18)	C77—N2—Ni1—N4	118.9 (8)
C47—N10—C41—C42	21.4 (12)	C78—N2—Ni1—Cl4	66.2 (9)
C49—N10—C41—C42	154.7 (11)	C77—N2—Ni1—Cl4	−128.2 (7)
C47—N10—C49—C48	−38.5 (13)	C78—N2—Ni1—Cl2	−154.9 (8)
C41—N10—C49—C48	−170.0 (11)	C77—N2—Ni1—Cl2	10.7 (8)
S1—C48—C49—N10	37.2 (12)	C47—N1—Ni2—N3	−45.4 (10)
C25—C26—C53—C22	1 (2)	C42—N1—Ni2—N3	131.3 (8)
C23—C22—C53—C26	1 (2)	C47—N1—Ni2—Cl1	−155.6 (9)
C47—N1—C42—C43	−108.2 (10)	C42—N1—Ni2—Cl1	21.1 (8)
Ni2—N1—C42—C43	74.5 (10)	C47—N1—Ni2—Cl3	60.9 (10)
C47—N1—C42—C41	12.7 (11)	C42—N1—Ni2—Cl3	−122.5 (8)
Ni2—N1—C42—C41	−164.7 (7)	C32—N3—Ni2—N1	−44.6 (10)
N10—C41—C42—C43	96.8 (10)	C1—N3—Ni2—N1	135.2 (9)
N10—C41—C42—N1	−20.4 (11)	C32—N3—Ni2—Cl1	61.6 (10)
C77—N2—C78—N55	−0.2 (13)	C1—N3—Ni2—Cl1	−118.7 (8)
Ni1—N2—C78—N55	167.7 (8)	C32—N3—Ni2—Cl3	−160.1 (9)
C77—N2—C78—S8	177.2 (8)	C1—N3—Ni2—Cl3	19.7 (9)
Ni1—N2—C78—S8	−14.9 (15)	N1—C47—S1—C48	178.7 (11)
N1—C42—C43—C45	−114.1 (11)	N10—C47—S1—C48	1.4 (10)
C41—C42—C43—C45	132.1 (10)	C49—C48—S1—C47	−22.8 (10)