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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 NiII compounds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805027893/su6211sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805027893/su6211Isup2.hkl
Contains datablock I

CCDC reference: 256949

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

Comment top

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.

Experimental top

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.

Refinement top

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 Uiso(H) = 1.2Ueq 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 top

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 top
[Figure 1] 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) top
Crystal data top
[NiCl2(C11H12N2S)2]F(000) = 1112
Mr = 538.19Dx = 1.497 Mg m3
Monoclinic, P21Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ybCell parameters from 4366 reflections
a = 8.1791 (5) Åθ = 1.4–69.6°
b = 9.2534 (4) ŵ = 5.00 mm1
c = 31.556 (2) ÅT = 200 K
β = 91.637 (3)°Plate, blue
V = 2387.3 (2) Å30.18 × 0.18 × 0.03 mm
Z = 4
Data collection top
Nonius KappaCCD area-detector
diffractometer
7693 independent reflections
Radiation source: fine-focus sealed tube6015 reflections with I > 2σ(I)
Horizontally mounted graphite crystal monochromatorRint = 0.061
Detector resolution: 9 pixels mm-1θmax = 69.6°, θmin = 1.4°
ϕ and ω scansh = 99
Absorption correction: part of the refinement model (ΔF)
(Parkin et al., 1995)
k = 119
Tmin = 0.476, Tmax = 0.866l = 3838
7693 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.076 w = 1/[σ2(Fo2) + (0.1088P)2 + 6.3761P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.245(Δ/σ)max = 0.001
S = 1.18Δρmax = 0.91 e Å3
7693 reflectionsΔρmin = 0.77 e Å3
559 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.0016 (3)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with how many Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.02 (4)
Crystal data top
[NiCl2(C11H12N2S)2]V = 2387.3 (2) Å3
Mr = 538.19Z = 4
Monoclinic, P21Cu Kα radiation
a = 8.1791 (5) ŵ = 5.00 mm1
b = 9.2534 (4) ÅT = 200 K
c = 31.556 (2) Å0.18 × 0.18 × 0.03 mm
β = 91.637 (3)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
7693 independent reflections
Absorption correction: part of the refinement model (ΔF)
(Parkin et al., 1995)
6015 reflections with I > 2σ(I)
Tmin = 0.476, Tmax = 0.866Rint = 0.061
7693 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.076H-atom parameters constrained
wR(F2) = 0.245Δρmax = 0.91 e Å3
S = 1.18Δρmin = 0.77 e Å3
7693 reflectionsAbsolute structure: Flack (1983), with how many Friedel pairs
559 parametersAbsolute structure parameter: 0.02 (4)
1 restraint
Special details top

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 (Å2) top
xyzUiso*/UeqOcc. (<1)
Cl40.4849 (3)0.8049 (4)0.96554 (8)0.0704 (9)
Cl30.1901 (4)0.5214 (4)0.66709 (10)0.0695 (8)
N20.4176 (10)0.6293 (11)0.8737 (2)0.050 (2)
N10.5049 (11)0.5507 (10)0.5956 (2)0.051 (2)
N30.5070 (10)0.3117 (10)0.6593 (2)0.050 (2)
N40.1232 (10)0.6740 (10)0.9290 (2)0.048 (2)
C10.4793 (13)0.2738 (14)0.7037 (3)0.056 (3)
H10.42480.35390.71790.067*
S70.7609 (4)0.2696 (4)0.60556 (9)0.0707 (8)
S50.1843 (4)0.6307 (4)1.01441 (9)0.0746 (9)
C250.0194 (16)0.5121 (17)0.7882 (4)0.074 (4)
H250.01680.54730.76060.089*
C220.0348 (13)0.4074 (14)0.8699 (4)0.065 (3)
H220.04340.37060.89730.078*
N100.7118 (10)0.7118 (10)0.5879 (2)0.051 (2)
C230.0011 (12)0.5518 (12)0.8641 (3)0.049 (2)
C260.0471 (16)0.3659 (17)0.7958 (4)0.077 (4)
H260.05930.30260.77320.092*
C240.0042 (13)0.6046 (15)0.8218 (3)0.060 (3)
H240.02380.70210.81670.072*
C110.0285 (10)0.6563 (12)0.8994 (3)0.045 (2)
H110.06010.75050.88760.054*
C210.1638 (14)0.6014 (19)0.9291 (4)0.078 (4)
H21A0.24620.67500.93330.094*
H21B0.21610.51500.91780.094*
N70.0740 (14)0.5709 (15)0.9680 (3)0.084 (4)
C100.0807 (15)0.6287 (14)0.9661 (3)0.060 (3)
C330.6569 (12)0.2556 (15)0.7224 (3)0.057 (3)
H33A0.70160.34650.73280.068*
H33B0.66210.18440.74500.068*
C360.3534 (14)0.0412 (14)0.6742 (3)0.061 (3)
H360.39040.06510.64750.074*
N60.7383 (11)0.2063 (10)0.6852 (3)0.055 (2)
C340.3793 (12)0.1362 (13)0.7080 (3)0.051 (2)
C320.6522 (12)0.2629 (13)0.6513 (3)0.052 (2)
C350.3178 (14)0.0969 (14)0.7473 (3)0.059 (3)
H350.33160.15880.77030.071*
C300.9366 (17)0.1848 (17)0.6334 (5)0.084 (4)
H30A0.93950.08210.62740.100*
H30B1.03800.22790.62440.100*
C310.9150 (13)0.2101 (18)0.6804 (4)0.075 (4)
H31A0.96830.13480.69710.090*
H31B0.95950.30310.68900.090*
C770.4486 (13)0.6427 (12)0.8274 (3)0.047 (2)
H770.34510.66180.81200.057*
C580.2750 (14)0.0854 (15)0.6800 (3)0.062 (3)
H580.26080.14870.65730.074*
C560.2372 (14)0.0320 (15)0.7522 (4)0.065 (3)
H560.19770.05670.77860.078*
C480.8361 (14)0.7707 (16)0.6542 (3)0.065 (3)
H48A0.79850.86890.65840.078*
H48B0.93320.75450.67190.078*
C410.6832 (13)0.6575 (14)0.5453 (3)0.055 (3)
H41A0.76920.59150.53730.066*
H41B0.67640.73590.52490.066*
C490.8724 (15)0.7441 (16)0.6072 (3)0.068 (3)
H49A0.91980.82930.59450.082*
H49B0.94670.66330.60410.082*
C530.0561 (17)0.3159 (15)0.8361 (4)0.078 (4)
H530.07710.21850.84100.094*
C420.5173 (12)0.5783 (12)0.5483 (3)0.049 (2)
H420.51960.48670.53270.059*
C780.4394 (13)0.4971 (14)0.8839 (3)0.054 (3)
C430.3734 (13)0.6674 (11)0.5338 (3)0.048 (2)
C470.6199 (13)0.6304 (12)0.6139 (3)0.048 (2)
C570.2150 (12)0.1227 (14)0.7194 (4)0.059 (3)
H570.16000.20960.72290.071*
C450.2557 (13)0.6109 (14)0.5059 (3)0.059 (3)
H450.27010.51800.49540.071*
C440.3461 (15)0.8078 (13)0.5484 (4)0.061 (3)
H440.42140.84880.56750.074*
C510.1346 (16)0.561 (2)1.0103 (4)0.086 (5)
H51A0.23250.61961.01200.104*
H51B0.16520.46161.01580.104*
C50A0.034 (2)0.522 (3)1.0381 (6)0.076 (5)*0.70
H50A0.06060.42021.03590.091*0.70
H50B0.02270.54671.06780.091*0.70
N550.4826 (14)0.4055 (14)0.8521 (3)0.080 (3)
C650.1147 (14)0.6895 (16)0.4930 (4)0.064 (3)
H650.03620.64780.47490.076*
C660.0954 (16)0.8263 (15)0.5072 (4)0.065 (3)
H660.00470.87940.49800.078*
C590.5101 (17)0.4911 (17)0.8158 (4)0.080 (4)
H59A0.44970.45340.79130.097*
H59B0.62550.49340.80950.097*
C670.2091 (16)0.8888 (15)0.5352 (4)0.071 (3)
H670.19440.98250.54510.085*
C990.5691 (12)0.7596 (13)0.8176 (3)0.051 (2)
C1040.6034 (14)0.7827 (14)0.7749 (3)0.059 (3)
H1040.54990.72860.75390.071*
C1010.7635 (14)0.9500 (12)0.8363 (3)0.056 (3)
H1010.81641.00580.85700.068*
C1000.6480 (14)0.8454 (13)0.8481 (3)0.056 (3)
H1000.62430.83350.87650.067*
C1030.7976 (14)0.9695 (14)0.7950 (4)0.064 (3)
H1030.87441.03810.78720.077*
C1020.7164 (16)0.8856 (16)0.7640 (4)0.072 (4)
H1020.73920.89970.73560.086*
S80.4305 (4)0.4129 (4)0.93304 (9)0.0645 (7)
C2010.5340 (17)0.2628 (18)0.8659 (6)0.098 (5)
H20A0.65250.25690.86720.118*
H20B0.49260.19020.84620.118*
C2000.466 (2)0.2379 (18)0.9095 (6)0.104 (6)
H20C0.54310.18300.92700.125*
H20D0.36430.18400.90720.125*
C50B0.039 (5)0.599 (5)1.0373 (11)0.056 (9)*0.30
H50C0.03210.52651.05950.067*0.30
H50D0.07660.68831.04980.067*0.30
Ni10.31525 (19)0.7756 (2)0.91004 (5)0.0483 (5)
Cl20.2100 (4)0.9477 (3)0.86709 (8)0.0633 (7)
Ni20.3531 (2)0.4157 (2)0.62077 (5)0.0508 (5)
S10.6777 (4)0.6425 (4)0.66674 (8)0.0611 (8)
Cl10.2914 (4)0.2683 (4)0.56682 (8)0.0732 (9)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl40.0603 (15)0.093 (3)0.0572 (14)0.0024 (16)0.0005 (11)0.0216 (15)
Cl30.0699 (18)0.0561 (19)0.0829 (19)0.0054 (15)0.0116 (14)0.0035 (15)
N20.055 (5)0.050 (6)0.045 (4)0.007 (4)0.002 (3)0.000 (4)
N10.064 (5)0.048 (6)0.042 (4)0.008 (4)0.000 (4)0.005 (4)
N30.051 (5)0.055 (6)0.044 (4)0.006 (4)0.000 (3)0.003 (4)
N40.048 (5)0.047 (6)0.048 (4)0.003 (4)0.001 (3)0.004 (4)
C10.071 (6)0.060 (7)0.038 (4)0.008 (6)0.005 (4)0.003 (5)
S70.0730 (18)0.072 (2)0.0679 (16)0.0005 (18)0.0211 (14)0.0014 (16)
S50.094 (2)0.082 (3)0.0477 (14)0.013 (2)0.0014 (13)0.0081 (14)
C250.071 (8)0.084 (11)0.066 (7)0.018 (8)0.004 (6)0.019 (7)
C220.048 (6)0.048 (7)0.097 (8)0.007 (6)0.021 (5)0.023 (7)
N100.052 (5)0.057 (6)0.044 (4)0.012 (4)0.004 (3)0.002 (4)
C230.038 (5)0.043 (7)0.064 (6)0.015 (5)0.004 (4)0.001 (5)
C260.065 (8)0.074 (10)0.090 (9)0.011 (7)0.031 (7)0.019 (7)
C240.062 (7)0.062 (8)0.057 (6)0.003 (6)0.001 (5)0.000 (5)
C110.032 (5)0.051 (7)0.051 (5)0.003 (4)0.001 (4)0.006 (4)
C210.053 (7)0.110 (13)0.071 (7)0.001 (8)0.003 (5)0.001 (7)
N70.074 (7)0.117 (11)0.063 (6)0.046 (7)0.013 (5)0.008 (6)
C100.076 (7)0.063 (8)0.040 (5)0.008 (7)0.003 (5)0.005 (5)
C330.048 (5)0.066 (8)0.057 (5)0.013 (6)0.006 (4)0.008 (5)
C360.072 (7)0.061 (8)0.052 (6)0.016 (6)0.005 (5)0.003 (5)
N60.056 (5)0.050 (6)0.059 (5)0.005 (4)0.003 (4)0.002 (4)
C340.049 (5)0.049 (7)0.055 (5)0.008 (5)0.007 (4)0.001 (5)
C320.043 (5)0.052 (7)0.060 (5)0.021 (5)0.006 (4)0.005 (5)
C350.071 (7)0.055 (8)0.052 (5)0.004 (6)0.014 (5)0.002 (5)
C300.074 (9)0.056 (9)0.122 (12)0.010 (7)0.019 (8)0.012 (8)
C310.035 (6)0.096 (11)0.094 (9)0.005 (6)0.001 (5)0.005 (7)
C770.054 (6)0.039 (6)0.048 (5)0.011 (5)0.009 (4)0.011 (4)
C580.072 (7)0.057 (8)0.058 (6)0.016 (7)0.008 (5)0.001 (6)
C560.063 (7)0.071 (9)0.061 (6)0.005 (6)0.016 (5)0.018 (6)
C480.066 (7)0.070 (9)0.060 (6)0.017 (7)0.006 (5)0.004 (6)
C410.050 (6)0.064 (8)0.051 (5)0.015 (6)0.000 (4)0.001 (5)
C490.073 (7)0.070 (9)0.061 (6)0.010 (7)0.002 (5)0.002 (6)
C530.094 (10)0.044 (8)0.095 (9)0.015 (7)0.037 (8)0.003 (7)
C420.057 (6)0.047 (6)0.044 (5)0.011 (5)0.001 (4)0.007 (4)
C780.049 (6)0.059 (8)0.053 (5)0.003 (5)0.012 (4)0.009 (5)
C430.057 (6)0.039 (6)0.047 (5)0.004 (5)0.002 (4)0.004 (4)
C470.059 (6)0.036 (6)0.049 (5)0.008 (5)0.007 (4)0.008 (4)
C570.044 (6)0.060 (8)0.075 (7)0.019 (5)0.001 (5)0.007 (6)
C450.058 (7)0.053 (7)0.067 (6)0.002 (6)0.005 (5)0.003 (5)
C440.076 (7)0.040 (7)0.068 (6)0.000 (6)0.000 (5)0.002 (5)
C510.067 (8)0.134 (15)0.059 (7)0.035 (9)0.017 (6)0.004 (8)
N550.099 (8)0.072 (8)0.066 (6)0.021 (7)0.026 (5)0.030 (6)
C650.049 (6)0.076 (10)0.066 (7)0.008 (6)0.004 (5)0.013 (6)
C660.071 (8)0.055 (8)0.068 (7)0.003 (6)0.003 (6)0.021 (6)
C590.078 (8)0.091 (11)0.075 (8)0.028 (8)0.034 (7)0.021 (7)
C670.079 (8)0.050 (8)0.083 (8)0.021 (7)0.014 (6)0.004 (6)
C990.048 (5)0.055 (7)0.051 (5)0.002 (5)0.011 (4)0.007 (5)
C1040.078 (7)0.058 (7)0.043 (5)0.000 (7)0.013 (5)0.002 (5)
C1010.065 (6)0.040 (7)0.064 (6)0.005 (5)0.012 (5)0.008 (5)
C1000.064 (7)0.058 (8)0.045 (5)0.010 (6)0.002 (4)0.005 (5)
C1030.053 (6)0.056 (8)0.084 (8)0.016 (6)0.012 (6)0.001 (6)
C1020.088 (9)0.071 (10)0.057 (6)0.005 (7)0.012 (6)0.010 (6)
S80.0700 (17)0.0515 (18)0.0712 (16)0.0025 (16)0.0093 (13)0.0050 (14)
C2010.062 (8)0.053 (9)0.180 (17)0.013 (7)0.022 (9)0.007 (10)
C2000.132 (14)0.060 (11)0.118 (13)0.029 (10)0.035 (11)0.019 (9)
Ni10.0515 (9)0.0486 (11)0.0452 (8)0.0012 (9)0.0070 (6)0.0033 (8)
Cl20.0724 (17)0.0579 (19)0.0596 (14)0.0068 (15)0.0034 (12)0.0058 (12)
Ni20.0546 (10)0.0503 (11)0.0472 (8)0.0080 (9)0.0029 (7)0.0030 (8)
S10.0718 (18)0.065 (2)0.0458 (13)0.0168 (16)0.0025 (11)0.0016 (12)
Cl10.097 (2)0.072 (2)0.0507 (13)0.0274 (19)0.0063 (13)0.0048 (14)
Geometric parameters (Å, º) top
Cl4—Ni12.220 (3)C58—C571.391 (14)
Cl3—Ni22.232 (3)C58—H580.9300
N2—C781.276 (15)C56—C571.342 (17)
N2—C771.497 (11)C56—H560.9300
N2—Ni11.975 (9)C48—C491.541 (15)
N1—C471.316 (13)C48—S11.808 (12)
N1—C421.521 (11)C48—H48A0.9700
N1—Ni21.946 (9)C48—H48B0.9700
N3—C321.302 (13)C41—C421.548 (14)
N3—C11.471 (11)C41—H41A0.9700
N3—Ni21.974 (9)C41—H41B0.9700
N4—C101.300 (13)C49—H49A0.9700
N4—C111.540 (12)C49—H49B0.9700
N4—Ni11.940 (8)C53—H530.9300
C1—C341.521 (16)C42—C431.497 (14)
C1—C331.561 (14)C42—H420.9800
C1—H10.9800C78—N551.369 (14)
S7—C321.719 (10)C78—S81.737 (12)
S7—C301.839 (14)C43—C451.389 (15)
S5—C101.722 (11)C43—C441.398 (15)
S5—C50A1.77 (2)C47—S11.723 (10)
S5—C50B2.00 (4)C57—H570.9300
C25—C241.381 (17)C45—C651.414 (16)
C25—C261.39 (2)C45—H450.9300
C25—H250.9300C44—C671.401 (16)
C22—C231.376 (17)C44—H440.9300
C22—C531.377 (18)C51—C50B1.20 (4)
C22—H220.9300C51—C50A1.65 (2)
N10—C471.357 (12)C51—H51A0.9700
N10—C411.447 (12)C51—H51B0.9700
N10—C491.463 (14)C50A—H50A0.9700
C23—C241.420 (14)C50A—H50B0.9700
C23—C111.502 (14)N55—C591.417 (18)
C26—C531.351 (19)N55—C2011.449 (19)
C26—H260.9300C65—C661.353 (18)
C24—H240.9300C65—H650.9300
C11—C211.555 (15)C66—C671.392 (18)
C11—H110.9800C66—H660.9300
C21—N71.439 (16)C59—H59A0.9700
C21—H21A0.9700C59—H59B0.9700
C21—H21B0.9700C67—H670.9300
N7—C101.377 (15)C99—C1001.393 (15)
N7—C511.442 (14)C99—C1041.400 (13)
C33—N61.441 (14)C104—C1021.378 (17)
C33—H33A0.9700C104—H1040.9300
C33—H33B0.9700C101—C1031.353 (15)
C36—C581.351 (17)C101—C1001.410 (16)
C36—C341.392 (15)C101—H1010.9300
C36—H360.9300C100—H1000.9300
N6—C321.366 (14)C103—C1021.401 (17)
N6—C311.458 (14)C103—H1030.9300
C34—C351.400 (14)C102—H1020.9300
C35—C561.374 (17)S8—C2001.808 (16)
C35—H350.9300C201—C2001.52 (2)
C30—C311.514 (19)C201—H20A0.9700
C30—H30A0.9700C201—H20B0.9700
C30—H30B0.9700C200—H20C0.9700
C31—H31A0.9700C200—H20D0.9700
C31—H31B0.9700C50B—H50C0.9700
C77—C991.502 (15)C50B—H50D0.9700
C77—C591.538 (18)Ni1—Cl22.247 (3)
C77—H770.9800Ni2—Cl12.228 (3)
C78—N2—C77107.5 (9)N10—C49—H49A111.0
C78—N2—Ni1124.7 (7)C48—C49—H49A111.0
C77—N2—Ni1126.6 (7)N10—C49—H49B111.0
C47—N1—C42105.7 (8)C48—C49—H49B111.0
C47—N1—Ni2129.6 (7)H49A—C49—H49B109.0
C42—N1—Ni2124.7 (7)C26—C53—C22120.9 (13)
C32—N3—C1105.4 (8)C26—C53—H53119.6
C32—N3—Ni2128.3 (7)C22—C53—H53119.6
C1—N3—Ni2126.2 (7)C43—C42—N1108.5 (8)
C10—N4—C11106.3 (8)C43—C42—C41113.8 (9)
C10—N4—Ni1132.3 (8)N1—C42—C41102.8 (7)
C11—N4—Ni1120.7 (6)C43—C42—H42110.5
N3—C1—C34112.4 (8)N1—C42—H42110.5
N3—C1—C33102.7 (8)C41—C42—H42110.5
C34—C1—C33111.9 (10)N2—C78—N55116.4 (11)
N3—C1—H1109.9N2—C78—S8130.2 (8)
C34—C1—H1109.9N55—C78—S8113.3 (10)
C33—C1—H1109.9C45—C43—C44116.3 (10)
C32—S7—C3089.9 (6)C45—C43—C42120.7 (10)
C10—S5—C50A92.1 (8)C44—C43—C42122.9 (10)
C10—S5—C50B83.6 (11)N1—C47—N10116.5 (9)
C24—C25—C26119.7 (14)N1—C47—S1129.3 (7)
C24—C25—H25120.2N10—C47—S1114.1 (8)
C26—C25—H25120.2C56—C57—C58119.4 (11)
C23—C22—C53121.5 (12)C56—C57—H57120.3
C23—C22—H22119.2C58—C57—H57120.3
C53—C22—H22119.2C43—C45—C65122.3 (12)
C47—N10—C41107.0 (8)C43—C45—H45118.9
C47—N10—C49111.5 (8)C65—C45—H45118.9
C41—N10—C49125.2 (9)C43—C44—C67122.3 (12)
C22—C23—C24117.4 (11)C43—C44—H44118.9
C22—C23—C11124.2 (10)C67—C44—H44118.9
C24—C23—C11118.4 (10)C50B—C51—N7114 (2)
C53—C26—C25120.0 (13)N7—C51—C50A101.6 (11)
C53—C26—H26120.0C50B—C51—H51A108.8
C25—C26—H26120.0N7—C51—H51A108.8
C25—C24—C23120.5 (13)C50A—C51—H51A140.4
C25—C24—H24119.7C50B—C51—H51B108.8
C23—C24—H24119.7N7—C51—H51B108.8
C23—C11—N4112.0 (8)C50A—C51—H51B85.1
C23—C11—C21111.7 (10)H51A—C51—H51B107.7
N4—C11—C21104.1 (8)C51—C50A—S5103.4 (12)
C23—C11—H11109.6C51—C50A—H50A111.1
N4—C11—H11109.6S5—C50A—H50A111.1
C21—C11—H11109.6C51—C50A—H50B111.1
N7—C21—C11102.9 (9)S5—C50A—H50B111.1
N7—C21—H21A111.2H50A—C50A—H50B109.1
C11—C21—H21A111.2C78—N55—C59107.4 (12)
N7—C21—H21B111.2C78—N55—C201115.0 (12)
C11—C21—H21B111.2C59—N55—C201134.5 (12)
H21A—C21—H21B109.1C66—C65—C45119.2 (12)
C10—N7—C21109.6 (10)C66—C65—H65120.4
C10—N7—C51113.9 (10)C45—C65—H65120.4
C21—N7—C51128.4 (11)C65—C66—C67121.2 (13)
N4—C10—N7115.7 (10)C65—C66—H66119.4
N4—C10—S5131.0 (9)C67—C66—H66119.4
N7—C10—S5113.3 (8)N55—C59—C77104.9 (9)
N6—C33—C199.9 (8)N55—C59—H59A110.8
N6—C33—H33A111.8C77—C59—H59A110.8
C1—C33—H33A111.8N55—C59—H59B110.8
N6—C33—H33B111.8C77—C59—H59B110.8
C1—C33—H33B111.8H59A—C59—H59B108.8
H33A—C33—H33B109.5C66—C67—C44118.7 (12)
C58—C36—C34120.5 (10)C66—C67—H67120.7
C58—C36—H36119.8C44—C67—H67120.7
C34—C36—H36119.8C100—C99—C104118.5 (11)
C32—N6—C33106.1 (9)C100—C99—C77124.2 (9)
C32—N6—C31113.5 (9)C104—C99—C77117.3 (10)
C33—N6—C31124.0 (9)C102—C104—C99119.9 (11)
C36—C34—C35117.6 (11)C102—C104—H104120.0
C36—C34—C1122.2 (9)C99—C104—H104120.0
C35—C34—C1120.2 (10)C103—C101—C100120.3 (11)
N3—C32—N6115.8 (9)C103—C101—H101119.8
N3—C32—S7130.2 (9)C100—C101—H101119.8
N6—C32—S7113.8 (8)C99—C100—C101120.6 (10)
C56—C35—C34120.8 (11)C99—C100—H100119.7
C56—C35—H35119.6C101—C100—H100119.7
C34—C35—H35119.6C101—C103—C102119.4 (11)
C31—C30—S7106.9 (9)C101—C103—H103120.3
C31—C30—H30A110.3C102—C103—H103120.3
S7—C30—H30A110.3C104—C102—C103121.2 (10)
C31—C30—H30B110.3C104—C102—H102119.4
S7—C30—H30B110.3C103—C102—H102119.4
H30A—C30—H30B108.6C78—S8—C20091.4 (7)
N6—C31—C30104.0 (10)N55—C201—C200107.5 (12)
N6—C31—H31A111.0N55—C201—H20A110.2
C30—C31—H31A111.0C200—C201—H20A110.2
N6—C31—H31B111.0N55—C201—H20B110.2
C30—C31—H31B111.0C200—C201—H20B110.2
H31A—C31—H31B109.0H20A—C201—H20B108.5
N2—C77—C99113.1 (8)C201—C200—S8107.7 (12)
N2—C77—C59102.9 (9)C201—C200—H20C110.2
C99—C77—C59112.8 (9)S8—C200—H20C110.2
N2—C77—H77109.3C201—C200—H20D110.2
C99—C77—H77109.3S8—C200—H20D110.2
C59—C77—H77109.3H20C—C200—H20D108.5
C36—C58—C57121.1 (11)C51—C50B—S5112 (2)
C36—C58—H58119.5C51—C50B—H50C109.2
C57—C58—H58119.5S5—C50B—H50C109.2
C57—C56—C35120.6 (10)C51—C50B—H50D109.2
C57—C56—H56119.7S5—C50B—H50D109.2
C35—C56—H56119.7H50C—C50B—H50D107.9
C49—C48—S1105.4 (9)N4—Ni1—N2102.0 (4)
C49—C48—H48A110.7N4—Ni1—Cl4108.0 (2)
S1—C48—H48A110.7N2—Ni1—Cl4106.0 (3)
C49—C48—H48B110.7N4—Ni1—Cl2103.3 (3)
S1—C48—H48B110.7N2—Ni1—Cl2107.3 (3)
H48A—C48—H48B108.8Cl4—Ni1—Cl2127.53 (16)
N10—C41—C42103.1 (8)N1—Ni2—N399.3 (4)
N10—C41—H41A111.1N1—Ni2—Cl1102.4 (3)
C42—C41—H41A111.1N3—Ni2—Cl1107.3 (3)
N10—C41—H41B111.1N1—Ni2—Cl3112.7 (3)
C42—C41—H41B111.1N3—Ni2—Cl3101.1 (3)
H41A—C41—H41B109.1Cl1—Ni2—Cl3129.95 (14)
N10—C49—C48103.8 (9)C47—S1—C4890.5 (5)
C32—N3—C1—C3497.8 (10)N1—C42—C43—C4463.5 (13)
Ni2—N3—C1—C3482.4 (12)C41—C42—C43—C4450.3 (13)
C32—N3—C1—C3322.7 (12)C42—N1—C47—N100.7 (13)
Ni2—N3—C1—C33157.1 (8)Ni2—N1—C47—N10177.8 (8)
C53—C22—C23—C242.6 (16)C42—N1—C47—S1176.7 (9)
C53—C22—C23—C11178.1 (10)Ni2—N1—C47—S10.5 (16)
C24—C25—C26—C532 (2)C41—N10—C47—N114.9 (13)
C26—C25—C24—C230.6 (19)C49—N10—C47—N1155.2 (10)
C22—C23—C24—C251.7 (16)C41—N10—C47—S1162.8 (8)
C11—C23—C24—C25178.8 (10)C49—N10—C47—S122.6 (12)
C22—C23—C11—N463.4 (13)C35—C56—C57—C580.3 (18)
C24—C23—C11—N4116.0 (10)C36—C58—C57—C560.8 (19)
C22—C23—C11—C2153.0 (13)C44—C43—C45—C650.5 (16)
C24—C23—C11—C21127.6 (10)C42—C43—C45—C65177.3 (10)
C10—N4—C11—C23117.4 (10)C45—C43—C44—C671.0 (16)
Ni1—N4—C11—C2371.2 (10)C42—C43—C44—C67178.7 (10)
C10—N4—C11—C213.5 (12)C10—N7—C51—C50B3 (3)
Ni1—N4—C11—C21168.0 (8)C21—N7—C51—C50B148 (3)
C23—C11—C21—N7111.7 (12)C10—N7—C51—C50A35.6 (19)
N4—C11—C21—N79.3 (14)C21—N7—C51—C50A179.4 (16)
C11—C21—N7—C1012.2 (16)C50B—C51—C50A—S577 (4)
C11—C21—N7—C51158.4 (15)N7—C51—C50A—S539.5 (16)
C11—N4—C10—N74.5 (15)C10—S5—C50A—C5128.1 (13)
Ni1—N4—C10—N7174.5 (9)C50B—S5—C50A—C5144 (2)
C11—N4—C10—S5174.4 (10)N2—C78—N55—C596.8 (15)
Ni1—N4—C10—S54.3 (19)S8—C78—N55—C59171.0 (9)
C21—N7—C10—N411.4 (17)N2—C78—N55—C201169.7 (11)
C51—N7—C10—N4162.9 (14)S8—C78—N55—C2018.1 (15)
C21—N7—C10—S5167.7 (11)C43—C45—C65—C662.0 (17)
C51—N7—C10—S516.1 (17)C45—C65—C66—C672.1 (17)
C50A—S5—C10—N4171.2 (15)C78—N55—C59—C779.8 (13)
C50B—S5—C10—N4162.5 (19)C201—N55—C59—C77167.9 (14)
C50A—S5—C10—N79.9 (13)N2—C77—C59—N559.4 (12)
C50B—S5—C10—N716.4 (16)C99—C77—C59—N55131.5 (10)
N3—C1—C33—N630.5 (11)C65—C66—C67—C440.7 (18)
C34—C1—C33—N690.2 (10)C43—C44—C67—C660.9 (18)
C1—C33—N6—C3227.8 (11)N2—C77—C99—C1001.5 (15)
C1—C33—N6—C31161.9 (11)C59—C77—C99—C100114.7 (12)
C58—C36—C34—C351.5 (18)N2—C77—C99—C104178.6 (9)
C58—C36—C34—C1174.8 (11)C59—C77—C99—C10465.2 (14)
N3—C1—C34—C3614.6 (16)C100—C99—C104—C1021.8 (17)
C33—C1—C34—C36100.4 (12)C77—C99—C104—C102178.1 (11)
N3—C1—C34—C35169.2 (10)C104—C99—C100—C1011.9 (16)
C33—C1—C34—C3575.8 (13)C77—C99—C100—C101178.0 (10)
C1—N3—C32—N65.5 (13)C103—C101—C100—C990.8 (17)
Ni2—N3—C32—N6174.2 (7)C100—C101—C103—C1020.5 (18)
C1—N3—C32—S7179.9 (9)C99—C104—C102—C1031 (2)
Ni2—N3—C32—S70.4 (16)C101—C103—C102—C1041 (2)
C33—N6—C32—N315.9 (13)N2—C78—S8—C200176.6 (12)
C31—N6—C32—N3155.4 (11)N55—C78—S8—C2006.0 (11)
C33—N6—C32—S7159.6 (8)C78—N55—C201—C20020.9 (18)
C31—N6—C32—S720.1 (13)C59—N55—C201—C200177.8 (15)
C30—S7—C32—N3176.2 (12)N55—C201—C200—S823.7 (17)
C30—S7—C32—N61.5 (10)C78—S8—C200—C20117.1 (12)
C36—C34—C35—C561.0 (17)N7—C51—C50B—S510 (4)
C1—C34—C35—C56175.4 (11)C50A—C51—C50B—S564 (3)
C32—S7—C30—C3121.0 (10)C10—S5—C50B—C5116 (3)
C32—N6—C31—C3034.9 (15)C50A—S5—C50B—C5192 (4)
C33—N6—C31—C30166.0 (11)C10—N4—Ni1—N2113.7 (11)
S7—C30—C31—N633.6 (13)C11—N4—Ni1—N277.5 (7)
C78—N2—C77—C99127.7 (10)C10—N4—Ni1—Cl42.2 (11)
Ni1—N2—C77—C9964.6 (11)C11—N4—Ni1—Cl4171.1 (6)
C78—N2—C77—C595.8 (11)C10—N4—Ni1—Cl2135.1 (11)
Ni1—N2—C77—C59173.4 (7)C11—N4—Ni1—Cl233.8 (7)
C34—C36—C58—C571.5 (19)C78—N2—Ni1—N446.7 (9)
C34—C35—C56—C570.4 (18)C77—N2—Ni1—N4118.9 (8)
C47—N10—C41—C4221.4 (12)C78—N2—Ni1—Cl466.2 (9)
C49—N10—C41—C42154.7 (11)C77—N2—Ni1—Cl4128.2 (7)
C47—N10—C49—C4838.5 (13)C78—N2—Ni1—Cl2154.9 (8)
C41—N10—C49—C48170.0 (11)C77—N2—Ni1—Cl210.7 (8)
S1—C48—C49—N1037.2 (12)C47—N1—Ni2—N345.4 (10)
C25—C26—C53—C221 (2)C42—N1—Ni2—N3131.3 (8)
C23—C22—C53—C261 (2)C47—N1—Ni2—Cl1155.6 (9)
C47—N1—C42—C43108.2 (10)C42—N1—Ni2—Cl121.1 (8)
Ni2—N1—C42—C4374.5 (10)C47—N1—Ni2—Cl360.9 (10)
C47—N1—C42—C4112.7 (11)C42—N1—Ni2—Cl3122.5 (8)
Ni2—N1—C42—C41164.7 (7)C32—N3—Ni2—N144.6 (10)
N10—C41—C42—C4396.8 (10)C1—N3—Ni2—N1135.2 (9)
N10—C41—C42—N120.4 (11)C32—N3—Ni2—Cl161.6 (10)
C77—N2—C78—N550.2 (13)C1—N3—Ni2—Cl1118.7 (8)
Ni1—N2—C78—N55167.7 (8)C32—N3—Ni2—Cl3160.1 (9)
C77—N2—C78—S8177.2 (8)C1—N3—Ni2—Cl319.7 (9)
Ni1—N2—C78—S814.9 (15)N1—C47—S1—C48178.7 (11)
N1—C42—C43—C45114.1 (11)N10—C47—S1—C481.4 (10)
C41—C42—C43—C45132.1 (10)C49—C48—S1—C4722.8 (10)

Experimental details

Crystal data
Chemical formula[NiCl2(C11H12N2S)2]
Mr538.19
Crystal system, space groupMonoclinic, P21
Temperature (K)200
a, b, c (Å)8.1791 (5), 9.2534 (4), 31.556 (2)
β (°) 91.637 (3)
V3)2387.3 (2)
Z4
Radiation typeCu Kα
µ (mm1)5.00
Crystal size (mm)0.18 × 0.18 × 0.03
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Absorption correctionPart of the refinement model (ΔF)
(Parkin et al., 1995)
Tmin, Tmax0.476, 0.866
No. of measured, independent and
observed [I > 2σ(I)] reflections
7693, 7693, 6015
Rint0.061
(sin θ/λ)max1)0.608
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.076, 0.245, 1.18
No. of reflections7693
No. of parameters559
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.91, 0.77
Absolute structureFlack (1983), with how many Friedel pairs
Absolute structure parameter0.02 (4)

Computer programs: COLLECT (Nonius, 1997–2000), SCALEPACK (Otwinowski & Minor, 1997), SCALEPACK and DENZO (Otwinowski & Minor, 1997), DIRDIF99 (Beurskens et al., 1999), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

 

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