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The Ni atom of the title compound, [Ni(C20H14ClN2OS)2]·CH2Cl2, shows a square-planar coordination geometry with two thio­carbonyl S and two carbonyl O atoms from two ligand moieties. The complex crystallizes with one solvent CH2Cl2 mol­ecule per asymmetric unit.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017069/cv6215sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017069/cv6215Isup2.hkl
Contains datablock I

CCDC reference: 188936

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.043
  • wR factor = 0.063
  • Data-to-parameter ratio = 15.9

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low ..... 0.98
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ..... ? PLAT244_ALERT_4_C Low Solvent U(eq) as Compared to Neighbors .. C100 PLAT431_ALERT_2_C Short Inter HL..A Contact:Cl12 .. N3 = 3.22 Ang. PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.# 2 C H2 Cl2
1 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

The title compound, (I), is another example of our newly synthesized thioureato metal complexes (Arslan et al., 2003). Its central Ni atom is almost square-planar, coordinated by two pairs of S and O atoms from the two chelating thioureate ligands, which show cis configurations (Fig. 1). Ni—O [mean 1.859 (2) Å] and Ni—S [mean 2.1394 (9) Å] bond lengths are in the expected ranges and compare well with those from the related dimethyl (Emen et al., 2003) or diethyl complex (Bailey et al., 1988). Both benzoyl ring planes subtend an angle of 79.9 (1)°; the corresponding torsion angles are O1—C7—C6—C1 130.9 (3)° and O2—C27—C26—C21 39.1 (4)°.

The crystal packing shows the molecules stacked in parallel sheets along [100] (Fig. 2) accompanied by the following intermolecular contacts: C31—H31A···O1i, with H···O 2.46 Å and C—H···O 152°; C10—H10A···Cl2ii, with H···Cl 2.78 Å and C—H···Cl 157°, and C19—H19A···Cl1iii, with H···Cl 2.87 Å and C—H···Cl 126° [symmetry codes: (i) −x, 1 − y, −z; (ii) x + 1, +y, +z; (iii) 2 − x, 2 − y, 1 − z]. Possible intramolecular interactions are C5—H5A···O1, with H—O 2.61 Å and C—H···O 90°, and C25—H25A···N3, with H···N 2.52 Å and C—H···N 94°. All these values are normalized for C—H = 1.08 Å. There is one solvent dichloromethane molecule per asymmetric unit.

Experimental top

Compound (I) was prepared according to the method of Polat (2002) by converting 2-chlorobenzoyl chloride into 2-chlorobenzoyl isothiocyanate and then condensing with diphenylamine in CH2Cl2 solution at 298 K. The compound was recrystallized from ethanol-dichloromethane.

Refinement top

H atoms were placed at calculated positions, riding on their parent C atoms, with isotropic displacement parameters Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SMART; data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXTL (Bruker, 2002); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level. The solvent CH2Cl2 molecule has been omitted.
[Figure 2] Fig. 2. Packing diagram for (I), viewed along [100]. Intermolecular C—H···Cl contacts are indicated by dashed lines.
cis-Bis[N-(2-chlorobenzoyl)-N',N'-diphenylthioureato]nickel(II) dichloromethane solvate top
Crystal data top
[Ni(C20H14ClN2OS)2]·CH2Cl2Z = 2
Mr = 875.32F(000) = 896
Triclinic, P1Dx = 1.500 Mg m3
a = 8.4277 (7) ÅMo Kα radiation, λ = 0.71073 Å
b = 14.2923 (11) ÅCell parameters from 1694 reflections
c = 17.4582 (13) Åθ = 2.5–23.3°
α = 103.671 (2)°µ = 0.93 mm1
β = 98.230 (2)°T = 173 K
γ = 103.877 (2)°Prism, red
V = 1938.6 (3) Å30.20 × 0.18 × 0.10 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
7764 independent reflections
Radiation source: sealed tube4564 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ϕ and ω scansθmax = 26.4°, θmin = 1.2°
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
h = 1010
Tmin = 0.818, Tmax = 0.912k = 1417
11475 measured reflectionsl = 2121
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.043Hydrogen site location: difference Fourier map
wR(F2) = 0.063H-atom parameters constrained
S = 0.81 w = 1/[σ2(Fo2) + (0.0001P)2]
where P = (Fo2 + 2Fc2)/3
7764 reflections(Δ/σ)max = 0.001
487 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
[Ni(C20H14ClN2OS)2]·CH2Cl2γ = 103.877 (2)°
Mr = 875.32V = 1938.6 (3) Å3
Triclinic, P1Z = 2
a = 8.4277 (7) ÅMo Kα radiation
b = 14.2923 (11) ŵ = 0.93 mm1
c = 17.4582 (13) ÅT = 173 K
α = 103.671 (2)°0.20 × 0.18 × 0.10 mm
β = 98.230 (2)°
Data collection top
Bruker SMART CCD area-detector
diffractometer
7764 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2002)
4564 reflections with I > 2σ(I)
Tmin = 0.818, Tmax = 0.912Rint = 0.038
11475 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.063H-atom parameters constrained
S = 0.81Δρmax = 0.48 e Å3
7764 reflectionsΔρmin = 0.37 e Å3
487 parameters
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*/Ueq
Ni10.22140 (5)0.52946 (3)0.24514 (2)0.02097 (11)
Cl10.72290 (11)0.89841 (6)0.35893 (6)0.0369 (2)
Cl20.17912 (13)0.67009 (7)0.23857 (5)0.0488 (3)
S10.43380 (10)0.50547 (6)0.31210 (5)0.0257 (2)
S20.13324 (10)0.36949 (6)0.19730 (5)0.0237 (2)
O10.2875 (3)0.66783 (14)0.29061 (12)0.0277 (6)
O20.0476 (3)0.55418 (15)0.18198 (13)0.0306 (6)
N10.5224 (3)0.70780 (17)0.39525 (14)0.0193 (6)
N20.6753 (3)0.61125 (18)0.43621 (14)0.0192 (6)
N30.1095 (3)0.40061 (18)0.08882 (14)0.0185 (6)
N40.0811 (3)0.24425 (18)0.07052 (15)0.0211 (6)
C10.5332 (4)0.9151 (2)0.37815 (18)0.0230 (8)
C20.5208 (4)1.0123 (2)0.39830 (19)0.0314 (9)
H2A0.61581.06740.40500.038*
C30.3690 (5)1.0285 (3)0.4085 (2)0.0358 (9)
H3B0.35981.09510.42380.043*
C40.2314 (5)0.9480 (3)0.3966 (2)0.0382 (10)
H4A0.12630.95880.40230.046*
C50.2459 (4)0.8514 (2)0.37627 (19)0.0283 (9)
H5A0.14960.79630.36750.034*
C60.3972 (4)0.8330 (2)0.36846 (17)0.0199 (8)
C70.4031 (4)0.7263 (2)0.34818 (18)0.0193 (7)
C80.5456 (4)0.6167 (2)0.38337 (18)0.0189 (7)
C90.7299 (4)0.5213 (2)0.42885 (18)0.0180 (7)
C100.8301 (4)0.4997 (2)0.3758 (2)0.0313 (9)
H10A0.85970.54200.34260.038*
C110.8877 (4)0.4166 (3)0.3708 (2)0.0357 (10)
H11A0.95640.40110.33380.043*
C120.8453 (4)0.3561 (2)0.4196 (2)0.0334 (9)
H12A0.88410.29840.41610.040*
C130.7481 (4)0.3786 (2)0.4730 (2)0.0366 (10)
H13A0.72020.33670.50690.044*
C140.6895 (4)0.4618 (2)0.4785 (2)0.0292 (9)
H14A0.62210.47770.51610.035*
C150.7756 (4)0.6997 (2)0.50020 (19)0.0189 (7)
C160.7608 (4)0.7058 (2)0.57851 (19)0.0278 (8)
H16A0.68130.65480.59050.033*
C170.8644 (4)0.7881 (2)0.63985 (19)0.0293 (9)
H17A0.85550.79350.69430.035*
C180.9792 (4)0.8615 (2)0.62222 (19)0.0272 (8)
H18A1.05000.91730.66440.033*
C190.9917 (4)0.8542 (2)0.5436 (2)0.0262 (8)
H19A1.06990.90550.53130.031*
C200.8909 (4)0.7725 (2)0.48265 (19)0.0246 (8)
H20A0.90150.76660.42840.030*
C210.2322 (4)0.6294 (2)0.13403 (19)0.0271 (8)
C220.3331 (4)0.6763 (2)0.0967 (2)0.0375 (10)
H22A0.36680.72900.12820.045*
C230.3840 (4)0.6471 (3)0.0149 (2)0.0387 (10)
H23A0.45100.68070.01030.046*
C240.3391 (4)0.5688 (3)0.0320 (2)0.0310 (9)
H24A0.37510.54840.08900.037*
C250.2409 (4)0.5211 (2)0.00581 (19)0.0256 (8)
H25A0.21140.46670.02600.031*
C260.1845 (4)0.5504 (2)0.08888 (19)0.0213 (8)
C270.0718 (4)0.4983 (2)0.12550 (19)0.0205 (8)
C280.0267 (4)0.3419 (2)0.11511 (18)0.0180 (7)
C290.2027 (4)0.2116 (2)0.00486 (19)0.0207 (8)
C300.1630 (4)0.2449 (2)0.0693 (2)0.0307 (9)
H30A0.05810.29200.06370.037*
C310.2770 (5)0.2095 (3)0.1424 (2)0.0415 (10)
H31A0.25080.23290.18700.050*
C320.4286 (5)0.1404 (3)0.1505 (2)0.0424 (11)
H32A0.50590.11550.20100.051*
C330.4675 (4)0.1078 (2)0.0867 (2)0.0376 (10)
H33A0.57230.06050.09270.045*
C340.3554 (4)0.1430 (2)0.0128 (2)0.0279 (9)
H34A0.38320.12030.03180.033*
C350.0105 (4)0.1682 (2)0.09150 (18)0.0214 (8)
C360.1211 (4)0.1481 (2)0.0589 (2)0.0306 (9)
H36A0.16670.18470.02440.037*
C370.1857 (4)0.0744 (3)0.0767 (2)0.0418 (10)
H37A0.27840.06130.05560.050*
C380.1180 (5)0.0198 (3)0.1246 (2)0.0432 (11)
H38A0.16280.03170.13590.052*
C390.0153 (5)0.0390 (2)0.1569 (2)0.0398 (10)
H39A0.06240.00090.19010.048*
C400.0802 (4)0.1149 (2)0.14009 (18)0.0293 (9)
H40A0.17140.12930.16200.035*
C1000.4973 (4)1.2590 (2)0.24215 (19)0.0356 (9)
H10B0.37511.24480.22350.043*
H10C0.53131.31020.29530.043*
Cl110.54216 (14)1.14915 (7)0.25308 (7)0.0600 (3)
Cl120.59950 (12)1.30724 (7)0.17371 (6)0.0476 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0201 (3)0.0150 (2)0.0216 (3)0.00395 (19)0.0052 (2)0.00037 (18)
Cl10.0225 (5)0.0267 (5)0.0579 (7)0.0027 (4)0.0023 (5)0.0132 (5)
Cl20.0661 (8)0.0489 (7)0.0311 (6)0.0330 (6)0.0010 (5)0.0007 (5)
S10.0234 (5)0.0168 (5)0.0286 (5)0.0057 (4)0.0086 (4)0.0007 (4)
S20.0230 (5)0.0168 (5)0.0242 (5)0.0039 (4)0.0065 (4)0.0009 (4)
O10.0255 (14)0.0156 (13)0.0315 (15)0.0034 (11)0.0128 (11)0.0007 (10)
O20.0272 (15)0.0157 (13)0.0358 (16)0.0037 (11)0.0147 (12)0.0022 (11)
N10.0184 (16)0.0150 (15)0.0210 (16)0.0035 (12)0.0015 (13)0.0035 (12)
N20.0174 (16)0.0164 (15)0.0194 (16)0.0035 (12)0.0028 (13)0.0025 (12)
N30.0202 (16)0.0145 (15)0.0176 (15)0.0048 (12)0.0023 (12)0.0021 (12)
N40.0233 (17)0.0146 (15)0.0203 (16)0.0041 (13)0.0016 (13)0.0003 (12)
C10.025 (2)0.0186 (19)0.022 (2)0.0048 (16)0.0037 (16)0.0058 (15)
C20.034 (2)0.017 (2)0.035 (2)0.0036 (17)0.0093 (18)0.0062 (16)
C30.050 (3)0.021 (2)0.035 (2)0.015 (2)0.000 (2)0.0043 (17)
C40.040 (3)0.036 (2)0.046 (3)0.024 (2)0.010 (2)0.013 (2)
C50.027 (2)0.019 (2)0.038 (2)0.0074 (17)0.0057 (18)0.0064 (17)
C60.023 (2)0.0173 (19)0.0161 (19)0.0064 (16)0.0024 (15)0.0022 (14)
C70.021 (2)0.0173 (19)0.0153 (19)0.0026 (15)0.0043 (16)0.0008 (14)
C80.0162 (19)0.0217 (19)0.0168 (19)0.0022 (15)0.0035 (15)0.0050 (15)
C90.0124 (18)0.0151 (18)0.0206 (19)0.0021 (14)0.0065 (15)0.0015 (15)
C100.037 (2)0.025 (2)0.034 (2)0.0106 (18)0.0082 (19)0.0098 (17)
C110.041 (3)0.039 (3)0.030 (2)0.020 (2)0.010 (2)0.0041 (19)
C120.029 (2)0.031 (2)0.037 (2)0.0146 (18)0.0061 (19)0.0047 (18)
C130.042 (3)0.034 (2)0.042 (3)0.017 (2)0.008 (2)0.0189 (19)
C140.026 (2)0.028 (2)0.038 (2)0.0111 (17)0.0114 (18)0.0116 (18)
C150.0160 (19)0.0175 (19)0.020 (2)0.0058 (15)0.0027 (15)0.0028 (15)
C160.029 (2)0.019 (2)0.028 (2)0.0027 (16)0.0034 (18)0.0037 (16)
C170.032 (2)0.034 (2)0.019 (2)0.0081 (18)0.0041 (17)0.0035 (17)
C180.025 (2)0.019 (2)0.027 (2)0.0031 (16)0.0038 (17)0.0019 (16)
C190.023 (2)0.021 (2)0.028 (2)0.0007 (16)0.0029 (17)0.0069 (16)
C200.025 (2)0.026 (2)0.020 (2)0.0036 (16)0.0004 (17)0.0077 (16)
C210.030 (2)0.024 (2)0.027 (2)0.0084 (17)0.0016 (17)0.0085 (16)
C220.038 (3)0.029 (2)0.049 (3)0.0159 (19)0.005 (2)0.013 (2)
C230.032 (2)0.041 (3)0.051 (3)0.011 (2)0.001 (2)0.030 (2)
C240.023 (2)0.043 (2)0.025 (2)0.0014 (18)0.0015 (17)0.0172 (18)
C250.021 (2)0.026 (2)0.027 (2)0.0017 (16)0.0013 (17)0.0086 (16)
C260.0157 (19)0.0180 (19)0.026 (2)0.0010 (15)0.0018 (16)0.0069 (15)
C270.020 (2)0.023 (2)0.019 (2)0.0074 (16)0.0049 (16)0.0058 (15)
C280.0207 (19)0.0154 (18)0.0157 (18)0.0012 (15)0.0050 (15)0.0038 (14)
C290.025 (2)0.0103 (18)0.022 (2)0.0063 (15)0.0034 (16)0.0021 (14)
C300.037 (2)0.019 (2)0.031 (2)0.0044 (17)0.0013 (19)0.0045 (17)
C310.069 (3)0.035 (2)0.024 (2)0.024 (2)0.001 (2)0.0100 (18)
C320.047 (3)0.037 (3)0.030 (2)0.019 (2)0.021 (2)0.0038 (19)
C330.025 (2)0.033 (2)0.040 (3)0.0042 (18)0.0089 (19)0.0010 (19)
C340.027 (2)0.026 (2)0.029 (2)0.0075 (17)0.0016 (18)0.0078 (17)
C350.023 (2)0.0127 (18)0.0188 (19)0.0031 (15)0.0089 (16)0.0032 (14)
C360.030 (2)0.022 (2)0.034 (2)0.0060 (17)0.0010 (18)0.0026 (16)
C370.032 (2)0.030 (2)0.055 (3)0.013 (2)0.001 (2)0.001 (2)
C380.055 (3)0.022 (2)0.039 (3)0.016 (2)0.022 (2)0.0040 (18)
C390.063 (3)0.021 (2)0.028 (2)0.007 (2)0.004 (2)0.0055 (17)
C400.038 (2)0.024 (2)0.020 (2)0.0074 (18)0.0006 (17)0.0000 (16)
C1000.037 (2)0.040 (2)0.031 (2)0.0136 (19)0.0085 (19)0.0097 (18)
Cl110.0673 (8)0.0436 (7)0.0697 (8)0.0185 (6)0.0023 (7)0.0217 (6)
Cl120.0500 (7)0.0565 (7)0.0377 (6)0.0138 (5)0.0122 (5)0.0153 (5)
Geometric parameters (Å, º) top
Ni1—O11.859 (2)C16—H16A0.9500
Ni1—O21.859 (2)C17—C181.372 (4)
Ni1—S12.1384 (9)C17—H17A0.9500
Ni1—S22.1405 (9)C18—C191.372 (4)
Cl1—C11.739 (3)C18—H18A0.9500
Cl2—C211.735 (3)C19—C201.377 (4)
S1—C81.725 (3)C19—H19A0.9500
S2—C281.719 (3)C20—H20A0.9500
O1—C71.261 (3)C21—C221.386 (4)
O2—C271.258 (4)C21—C261.395 (4)
N1—C71.323 (3)C22—C231.360 (4)
N1—C81.335 (3)C22—H22A0.9500
N2—C81.356 (3)C23—C241.387 (4)
N2—C91.450 (3)C23—H23A0.9500
N2—C151.452 (4)C24—C251.383 (4)
N3—C271.329 (3)C24—H24A0.9500
N3—C281.332 (3)C25—C261.387 (4)
N4—C281.357 (3)C25—H25A0.9500
N4—C291.447 (4)C26—C271.502 (4)
N4—C351.451 (3)C29—C301.374 (4)
C1—C21.383 (4)C29—C341.385 (4)
C1—C61.387 (4)C30—C311.385 (4)
C2—C31.382 (4)C30—H30A0.9500
C2—H2A0.9500C31—C321.380 (5)
C3—C41.375 (4)C31—H31A0.9500
C3—H3B0.9500C32—C331.357 (4)
C4—C51.382 (4)C32—H32A0.9500
C4—H4A0.9500C33—C341.388 (4)
C5—C61.381 (4)C33—H33A0.9500
C5—H5A0.9500C34—H34A0.9500
C6—C71.496 (4)C35—C401.371 (4)
C9—C101.370 (4)C35—C361.376 (4)
C9—C141.372 (4)C36—C371.372 (4)
C10—C111.376 (4)C36—H36A0.9500
C10—H10A0.9500C37—C381.366 (4)
C11—C121.374 (4)C37—H37A0.9500
C11—H11A0.9500C38—C391.382 (4)
C12—C131.358 (4)C38—H38A0.9500
C12—H12A0.9500C39—C401.396 (4)
C13—C141.383 (4)C39—H39A0.9500
C13—H13A0.9500C40—H40A0.9500
C14—H14A0.9500C100—Cl121.745 (3)
C15—C201.368 (4)C100—Cl111.747 (3)
C15—C161.375 (4)C100—H10B0.9900
C16—C171.392 (4)C100—H10C0.9900
O1—Ni1—O284.04 (9)C18—C19—C20120.0 (3)
O1—Ni1—S194.83 (7)C18—C19—H19A120.0
O2—Ni1—S1175.54 (8)C20—C19—H19A120.0
O1—Ni1—S2176.33 (7)C15—C20—C19120.0 (3)
O2—Ni1—S295.15 (7)C15—C20—H20A120.0
S1—Ni1—S286.24 (3)C19—C20—H20A120.0
C8—S1—Ni1108.58 (11)C22—C21—C26120.7 (3)
C28—S2—Ni1107.82 (10)C22—C21—Cl2116.4 (3)
C7—O1—Ni1133.1 (2)C26—C21—Cl2122.8 (2)
C27—O2—Ni1132.9 (2)C23—C22—C21120.2 (3)
C7—N1—C8122.3 (3)C23—C22—H22A119.9
C8—N2—C9122.9 (3)C21—C22—H22A119.9
C8—N2—C15120.5 (2)C22—C23—C24120.8 (3)
C9—N2—C15116.5 (2)C22—C23—H23A119.6
C27—N3—C28121.9 (3)C24—C23—H23A119.6
C28—N4—C29121.7 (2)C25—C24—C23118.8 (3)
C28—N4—C35122.2 (3)C25—C24—H24A120.6
C29—N4—C35115.9 (2)C23—C24—H24A120.6
C2—C1—C6121.7 (3)C24—C25—C26121.8 (3)
C2—C1—Cl1117.5 (3)C24—C25—H25A119.1
C6—C1—Cl1120.7 (2)C26—C25—H25A119.1
C3—C2—C1119.5 (3)C25—C26—C21117.8 (3)
C3—C2—H2A120.3C25—C26—C27118.9 (3)
C1—C2—H2A120.3C21—C26—C27123.3 (3)
C4—C3—C2119.7 (3)O2—C27—N3130.5 (3)
C4—C3—H3B120.2O2—C27—C26115.6 (3)
C2—C3—H3B120.2N3—C27—C26113.8 (3)
C3—C4—C5120.1 (3)N3—C28—N4114.2 (3)
C3—C4—H4A120.0N3—C28—S2130.4 (2)
C5—C4—H4A120.0N4—C28—S2115.4 (2)
C6—C5—C4121.5 (3)C30—C29—C34120.3 (3)
C6—C5—H5A119.3C30—C29—N4119.9 (3)
C4—C5—H5A119.3C34—C29—N4119.7 (3)
C5—C6—C1117.5 (3)C29—C30—C31119.6 (3)
C5—C6—C7118.2 (3)C29—C30—H30A120.2
C1—C6—C7124.3 (3)C31—C30—H30A120.2
O1—C7—N1130.6 (3)C32—C31—C30120.1 (3)
O1—C7—C6113.8 (3)C32—C31—H31A119.9
N1—C7—C6115.5 (3)C30—C31—H31A119.9
N1—C8—N2114.7 (3)C33—C32—C31120.2 (4)
N1—C8—S1129.7 (2)C33—C32—H32A119.9
N2—C8—S1115.6 (2)C31—C32—H32A119.9
C10—C9—C14120.4 (3)C32—C33—C34120.6 (3)
C10—C9—N2119.7 (3)C32—C33—H33A119.7
C14—C9—N2119.7 (3)C34—C33—H33A119.7
C9—C10—C11120.0 (3)C29—C34—C33119.2 (3)
C9—C10—H10A120.0C29—C34—H34A120.4
C11—C10—H10A120.0C33—C34—H34A120.4
C12—C11—C10119.6 (3)C40—C35—C36121.3 (3)
C12—C11—H11A120.2C40—C35—N4119.8 (3)
C10—C11—H11A120.2C36—C35—N4118.8 (3)
C13—C12—C11120.3 (3)C37—C36—C35119.2 (3)
C13—C12—H12A119.9C37—C36—H36A120.4
C11—C12—H12A119.9C35—C36—H36A120.4
C12—C13—C14120.6 (3)C38—C37—C36120.7 (3)
C12—C13—H13A119.7C38—C37—H37A119.7
C14—C13—H13A119.7C36—C37—H37A119.7
C9—C14—C13119.1 (3)C37—C38—C39120.4 (3)
C9—C14—H14A120.5C37—C38—H38A119.8
C13—C14—H14A120.5C39—C38—H38A119.8
C20—C15—C16120.8 (3)C38—C39—C40119.4 (3)
C20—C15—N2119.8 (3)C38—C39—H39A120.3
C16—C15—N2119.3 (3)C40—C39—H39A120.3
C15—C16—C17118.8 (3)C35—C40—C39119.0 (3)
C15—C16—H16A120.6C35—C40—H40A120.5
C17—C16—H16A120.6C39—C40—H40A120.5
C18—C17—C16120.4 (3)Cl12—C100—Cl11112.29 (17)
C18—C17—H17A119.8Cl12—C100—H10B109.1
C16—C17—H17A119.8Cl11—C100—H10B109.1
C17—C18—C19120.0 (3)Cl12—C100—H10C109.1
C17—C18—H18A120.0Cl11—C100—H10C109.1
C19—C18—H18A120.0H10B—C100—H10C107.9
O1—Ni1—S1—C88.05 (12)C17—C18—C19—C201.1 (5)
S2—Ni1—S1—C8168.43 (11)C16—C15—C20—C191.3 (5)
O2—Ni1—S2—C2810.04 (13)N2—C15—C20—C19177.0 (3)
S1—Ni1—S2—C28165.71 (11)C18—C19—C20—C151.5 (5)
O2—Ni1—O1—C7175.8 (3)C26—C21—C22—C231.4 (5)
S1—Ni1—O1—C78.6 (3)Cl2—C21—C22—C23178.3 (3)
O1—Ni1—O2—C27177.7 (3)C21—C22—C23—C241.4 (5)
S2—Ni1—O2—C275.9 (3)C22—C23—C24—C250.2 (5)
C6—C1—C2—C30.5 (5)C23—C24—C25—C261.0 (5)
Cl1—C1—C2—C3175.5 (3)C24—C25—C26—C211.0 (5)
C1—C2—C3—C41.7 (5)C24—C25—C26—C27177.2 (3)
C2—C3—C4—C51.5 (5)C22—C21—C26—C250.2 (5)
C3—C4—C5—C60.8 (5)Cl2—C21—C26—C25176.9 (2)
C4—C5—C6—C12.9 (5)C22—C21—C26—C27178.3 (3)
C4—C5—C6—C7178.6 (3)Cl2—C21—C26—C274.9 (5)
C2—C1—C6—C52.7 (5)Ni1—O2—C27—N33.7 (5)
Cl1—C1—C6—C5173.1 (2)Ni1—O2—C27—C26178.69 (19)
C2—C1—C6—C7178.9 (3)C28—N3—C27—O27.5 (5)
Cl1—C1—C6—C75.3 (4)C28—N3—C27—C26177.4 (3)
Ni1—O1—C7—N12.3 (5)C25—C26—C27—O2139.0 (3)
Ni1—O1—C7—C6174.18 (19)C21—C26—C27—O239.1 (4)
C8—N1—C7—O15.2 (5)C25—C26—C27—N336.9 (4)
C8—N1—C7—C6178.4 (3)C21—C26—C27—N3145.0 (3)
C5—C6—C7—O147.5 (4)C27—N3—C28—N4179.8 (3)
C1—C6—C7—O1130.9 (3)C27—N3—C28—S22.0 (5)
C5—C6—C7—N1129.5 (3)C29—N4—C28—N38.0 (4)
C1—C6—C7—N152.1 (4)C35—N4—C28—N3177.6 (3)
C7—N1—C8—N2178.8 (3)C29—N4—C28—S2173.5 (2)
C7—N1—C8—S12.2 (4)C35—N4—C28—S20.9 (4)
C9—N2—C8—N1174.3 (2)Ni1—S2—C28—N310.9 (3)
C15—N2—C8—N10.8 (4)Ni1—S2—C28—N4170.91 (19)
C9—N2—C8—S16.6 (4)C28—N4—C29—C3064.8 (4)
C15—N2—C8—S1178.4 (2)C35—N4—C29—C30109.9 (3)
Ni1—S1—C8—N15.3 (3)C28—N4—C29—C34118.4 (3)
Ni1—S1—C8—N2173.65 (18)C35—N4—C29—C3466.9 (4)
C8—N2—C9—C1080.4 (4)C34—C29—C30—C310.0 (5)
C15—N2—C9—C1094.8 (3)N4—C29—C30—C31176.9 (3)
C8—N2—C9—C14103.6 (3)C29—C30—C31—C320.7 (5)
C15—N2—C9—C1481.2 (4)C30—C31—C32—C330.9 (5)
C14—C9—C10—C111.5 (5)C31—C32—C33—C340.4 (5)
N2—C9—C10—C11177.5 (3)C30—C29—C34—C330.4 (5)
C9—C10—C11—C120.5 (5)N4—C29—C34—C33176.4 (3)
C10—C11—C12—C130.5 (5)C32—C33—C34—C290.3 (5)
C11—C12—C13—C140.5 (5)C28—N4—C35—C4091.2 (4)
C10—C9—C14—C131.4 (5)C29—N4—C35—C4094.1 (3)
N2—C9—C14—C13177.4 (3)C28—N4—C35—C3691.7 (4)
C12—C13—C14—C90.4 (5)C29—N4—C35—C3682.9 (4)
C8—N2—C15—C2076.0 (4)C40—C35—C36—C371.3 (5)
C9—N2—C15—C2099.3 (3)N4—C35—C36—C37178.3 (3)
C8—N2—C15—C16108.3 (3)C35—C36—C37—C381.6 (5)
C9—N2—C15—C1676.4 (4)C36—C37—C38—C390.9 (6)
C20—C15—C16—C170.6 (5)C37—C38—C39—C400.1 (5)
N2—C15—C16—C17176.3 (3)C36—C35—C40—C390.3 (5)
C15—C16—C17—C180.1 (5)N4—C35—C40—C39177.3 (3)
C16—C17—C18—C190.4 (5)C38—C39—C40—C350.4 (5)

Experimental details

Crystal data
Chemical formula[Ni(C20H14ClN2OS)2]·CH2Cl2
Mr875.32
Crystal system, space groupTriclinic, P1
Temperature (K)173
a, b, c (Å)8.4277 (7), 14.2923 (11), 17.4582 (13)
α, β, γ (°)103.671 (2), 98.230 (2), 103.877 (2)
V3)1938.6 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.93
Crystal size (mm)0.20 × 0.18 × 0.10
Data collection
DiffractometerBruker SMART CCD area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2002)
Tmin, Tmax0.818, 0.912
No. of measured, independent and
observed [I > 2σ(I)] reflections
11475, 7764, 4564
Rint0.038
(sin θ/λ)max1)0.625
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.063, 0.81
No. of reflections7764
No. of parameters487
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.48, 0.37

Computer programs: SMART (Bruker, 2002), SMART, SAINT (Bruker, 2002), SHELXTL (Bruker, 2002), SHELXTL.

 

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