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The Ni atom of the title compound, [Ni(C10H10ClN2OS)2], shows square-planar coordination geometry with two thio­carbonyl S and two carbonyl O atoms from two ligand moieties.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014934/bt6300sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014934/bt6300Isup2.hkl
Contains datablock I

CCDC reference: 188937

Key indicators

  • Single-crystal X-ray study
  • T = 203 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.056
  • wR factor = 0.172
  • Data-to-parameter ratio = 18.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
PLAT_031 Alert C Refined Extinction Parameter within Range ...... 3.22 Sigma PLAT_710 Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 O2 -NI1 -S1 -C1 -56.00 4.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 5 O1 -NI1 -S2 -C11 -51.00 3.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 9 S2 -NI1 -O1 -C2 -133.00 3.00 1.555 1.555 1.555 1.555 PLAT_710 Alert C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11 S1 -NI1 -O2 -C12 -101.00 4.00 1.555 1.555 1.555 1.555
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
5 Alert Level C = Please check

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: SHELXTL (Bruker, 1998); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

cis-bis(N,N-dimethyl-N'-2-chlorobenzoylthioureato)nickel(II) top
Crystal data top
[Ni(C10H10ClN2OS)2]Dx = 1.598 Mg m3
Mr = 542.13Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, PbcaCell parameters from 29 reflections
a = 7.3679 (14) Åθ = 7.6–15.0°
b = 22.280 (4) ŵ = 1.31 mm1
c = 27.448 (4) ÅT = 203 K
V = 4505.8 (14) Å3Prism, violet
Z = 80.44 × 0.22 × 0.14 mm
F(000) = 2224
Data collection top
Bruker P4
diffractometer
2254 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 27.5°, θmin = 2.4°
ω scansh = 91
Absorption correction: ψ scan
(North et al., 1968)
k = 128
Tmin = 0.548, Tmax = 0.832l = 351
6492 measured reflections3 standard reflections every 397 reflections
5178 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.172 w = 1/[σ2(Fo2) + (0.0624P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
5178 reflectionsΔρmax = 0.54 e Å3
281 parametersΔρmin = 0.55 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.00029 (9)
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
Ni10.73553 (10)0.42207 (3)0.12268 (2)0.0304 (2)
Cl11.0080 (2)0.23999 (7)0.13739 (7)0.0539 (5)
Cl20.7657 (2)0.40590 (7)0.09794 (5)0.0438 (4)
S10.7372 (2)0.46328 (6)0.19322 (5)0.0407 (4)
S20.7369 (2)0.51140 (6)0.09348 (5)0.0403 (4)
O10.7264 (6)0.34354 (15)0.14619 (13)0.0391 (10)
O20.7407 (6)0.38496 (15)0.06211 (13)0.0377 (10)
N10.7259 (7)0.34810 (19)0.23166 (15)0.0314 (11)
N20.7356 (7)0.4270 (2)0.28378 (15)0.0394 (12)
N30.8001 (7)0.45882 (19)0.00342 (16)0.0330 (11)
N40.7227 (7)0.5573 (2)0.00576 (17)0.0352 (11)
C10.7323 (8)0.4080 (2)0.23762 (19)0.0320 (13)
C20.7225 (8)0.3221 (2)0.1889 (2)0.0346 (13)
C30.6976 (8)0.2550 (2)0.19103 (18)0.0322 (13)
C40.5497 (10)0.2320 (3)0.2160 (2)0.0445 (16)
H4A0.47090.25810.23260.053*
C50.5172 (10)0.1704 (3)0.2166 (2)0.0442 (16)
H5A0.41600.15520.23340.053*
C60.6327 (10)0.1315 (3)0.1926 (2)0.0465 (17)
H6A0.60910.09010.19300.056*
C70.7835 (9)0.1534 (2)0.1680 (2)0.0424 (16)
H7A0.86380.12710.15210.051*
C80.8132 (8)0.2150 (2)0.1675 (2)0.0342 (14)
C90.7328 (9)0.3849 (3)0.3250 (2)0.0477 (17)
H9A0.72940.34400.31280.072*
H9B0.62610.39230.34480.072*
H9C0.84100.39050.34460.072*
C100.7394 (9)0.4909 (3)0.2978 (2)0.0489 (17)
H10A0.74040.51570.26880.073*
H10B0.84770.49890.31690.073*
H10C0.63270.50020.31710.073*
C110.7530 (8)0.5069 (2)0.0307 (2)0.0331 (13)
C120.7966 (8)0.4038 (2)0.02090 (19)0.0312 (13)
C130.8686 (8)0.3548 (2)0.01044 (19)0.0296 (13)
C140.9483 (8)0.3060 (2)0.0141 (2)0.0385 (14)
H14A0.95130.30670.04830.046*
C151.0213 (9)0.2579 (2)0.0092 (2)0.0403 (15)
H15A1.07540.22660.00860.048*
C161.0147 (9)0.2558 (3)0.0598 (2)0.0431 (15)
H16A1.06680.22310.07630.052*
C170.9326 (9)0.3010 (3)0.0858 (2)0.0425 (15)
H17A0.92350.29820.11990.051*
C180.8625 (9)0.3511 (3)0.0615 (2)0.0373 (14)
C190.7412 (9)0.5592 (3)0.0475 (2)0.0453 (16)
H19A0.77850.52000.05930.068*
H19B0.83180.58880.05640.068*
H19C0.62560.56990.06200.068*
C200.6668 (9)0.6130 (2)0.0300 (2)0.0433 (16)
H20A0.65950.60640.06490.065*
H20B0.54890.62530.01780.065*
H20C0.75510.64430.02330.065*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ni10.0414 (5)0.0215 (3)0.0283 (3)0.0004 (4)0.0022 (4)0.0016 (3)
Cl10.0512 (11)0.0414 (9)0.0691 (11)0.0041 (8)0.0148 (9)0.0010 (8)
Cl20.0564 (10)0.0415 (8)0.0334 (7)0.0025 (8)0.0004 (8)0.0033 (6)
S10.0654 (11)0.0240 (6)0.0326 (7)0.0016 (8)0.0013 (9)0.0044 (6)
S20.0657 (11)0.0215 (6)0.0338 (7)0.0014 (8)0.0039 (9)0.0014 (5)
O10.064 (3)0.0235 (18)0.0294 (19)0.001 (2)0.004 (2)0.0011 (15)
O20.061 (3)0.0232 (18)0.0287 (19)0.007 (2)0.005 (2)0.0007 (15)
N10.044 (3)0.026 (2)0.024 (2)0.002 (2)0.000 (2)0.0036 (18)
N20.058 (3)0.034 (2)0.027 (2)0.004 (3)0.001 (3)0.006 (2)
N30.043 (3)0.021 (2)0.035 (2)0.002 (2)0.004 (2)0.0014 (19)
N40.042 (3)0.023 (2)0.041 (3)0.003 (2)0.002 (3)0.000 (2)
C10.031 (3)0.034 (3)0.031 (3)0.004 (3)0.002 (3)0.004 (2)
C20.044 (4)0.026 (3)0.033 (3)0.002 (3)0.003 (3)0.001 (2)
C30.049 (4)0.026 (3)0.021 (2)0.000 (3)0.004 (3)0.002 (2)
C40.064 (5)0.035 (3)0.035 (3)0.003 (3)0.009 (3)0.003 (3)
C50.055 (4)0.037 (3)0.040 (3)0.008 (3)0.006 (3)0.005 (3)
C60.070 (5)0.024 (3)0.046 (4)0.007 (3)0.005 (4)0.005 (3)
C70.065 (5)0.025 (3)0.038 (3)0.001 (3)0.005 (3)0.005 (2)
C80.046 (4)0.029 (3)0.028 (3)0.002 (3)0.002 (3)0.006 (2)
C90.068 (5)0.046 (4)0.029 (3)0.001 (4)0.002 (3)0.001 (3)
C100.061 (5)0.039 (3)0.047 (4)0.004 (4)0.000 (4)0.026 (3)
C110.037 (3)0.026 (3)0.036 (3)0.002 (3)0.003 (3)0.001 (2)
C120.040 (3)0.026 (3)0.027 (3)0.002 (3)0.003 (3)0.004 (2)
C130.039 (3)0.021 (3)0.029 (3)0.002 (3)0.001 (3)0.001 (2)
C140.044 (4)0.028 (3)0.043 (3)0.000 (3)0.004 (3)0.000 (3)
C150.046 (4)0.029 (3)0.046 (4)0.003 (3)0.004 (3)0.004 (3)
C160.043 (4)0.039 (3)0.047 (3)0.003 (3)0.006 (3)0.010 (3)
C170.042 (4)0.045 (4)0.040 (3)0.006 (3)0.009 (3)0.004 (3)
C180.039 (4)0.038 (3)0.035 (3)0.004 (3)0.006 (3)0.003 (3)
C190.057 (4)0.041 (3)0.039 (3)0.004 (4)0.005 (3)0.008 (3)
C200.050 (4)0.023 (3)0.056 (4)0.006 (3)0.005 (3)0.008 (3)
Geometric parameters (Å, º) top
Ni1—O21.857 (4)N4—C111.334 (7)
Ni1—O11.866 (4)N4—C201.468 (7)
Ni1—S12.1430 (15)N4—C191.470 (7)
Ni1—S22.1456 (15)C2—C31.508 (7)
Cl1—C81.747 (6)C3—C41.385 (8)
Cl2—C181.733 (6)C3—C81.392 (8)
S1—C11.733 (5)C4—C51.394 (8)
S2—C111.731 (6)C5—C61.381 (8)
O1—C21.265 (6)C6—C71.388 (9)
O2—C121.275 (6)C7—C81.391 (7)
N1—C21.310 (7)C12—C131.488 (7)
N1—C11.345 (7)C13—C181.403 (7)
N2—C11.336 (6)C13—C141.407 (7)
N2—C91.470 (7)C14—C151.359 (7)
N2—C101.477 (7)C15—C161.389 (8)
N3—C121.316 (7)C16—C171.375 (8)
N3—C111.352 (7)C17—C181.399 (8)
O2—Ni1—O183.85 (15)C4—C3—C2118.8 (5)
O2—Ni1—S1178.16 (15)C8—C3—C2122.8 (5)
O1—Ni1—S195.13 (12)C3—C4—C5120.4 (6)
O2—Ni1—S294.51 (12)C6—C5—C4120.4 (6)
O1—Ni1—S2177.54 (14)C5—C6—C7120.4 (5)
S1—Ni1—S286.55 (6)C6—C7—C8118.5 (6)
C1—S1—Ni1109.31 (19)C7—C8—C3122.1 (6)
C11—S2—Ni1108.57 (19)C7—C8—Cl1116.7 (5)
C2—O1—Ni1132.4 (3)C3—C8—Cl1121.2 (4)
C12—O2—Ni1130.8 (3)N4—C11—N3115.2 (5)
C2—N1—C1123.2 (5)N4—C11—S2116.8 (4)
C1—N2—C9121.9 (5)N3—C11—S2127.9 (4)
C1—N2—C10123.6 (5)O2—C12—N3129.5 (5)
C9—N2—C10114.5 (4)O2—C12—C13112.7 (5)
C12—N3—C11122.1 (5)N3—C12—C13117.7 (5)
C11—N4—C20121.8 (5)C18—C13—C14116.4 (5)
C11—N4—C19121.3 (5)C18—C13—C12127.5 (5)
C20—N4—C19116.9 (5)C14—C13—C12116.1 (5)
N2—C1—N1115.4 (5)C15—C14—C13123.3 (6)
N2—C1—S1116.2 (4)C14—C15—C16118.9 (6)
N1—C1—S1128.3 (4)C17—C16—C15120.6 (6)
O1—C2—N1131.6 (5)C16—C17—C18119.9 (6)
O1—C2—C3114.4 (5)C17—C18—C13120.8 (6)
N1—C2—C3113.9 (5)C17—C18—Cl2116.0 (5)
C4—C3—C8118.3 (5)C13—C18—Cl2123.2 (5)
O2—Ni1—S1—C156 (4)C6—C7—C8—C30.6 (9)
O1—Ni1—S1—C10.7 (3)C6—C7—C8—Cl1178.4 (5)
S2—Ni1—S1—C1178.9 (2)C4—C3—C8—C70.5 (9)
O2—Ni1—S2—C112.9 (3)C2—C3—C8—C7177.0 (5)
O1—Ni1—S2—C1151 (3)C4—C3—C8—Cl1177.2 (4)
S1—Ni1—S2—C11175.6 (2)C2—C3—C8—Cl15.3 (8)
O2—Ni1—O1—C2178.5 (6)C20—N4—C11—N3178.8 (5)
S1—Ni1—O1—C20.0 (6)C19—N4—C11—N30.3 (8)
S2—Ni1—O1—C2133 (3)C20—N4—C11—S23.9 (8)
O1—Ni1—O2—C12158.0 (6)C19—N4—C11—S2177.1 (4)
S1—Ni1—O2—C12101 (4)C12—N3—C11—N4165.2 (6)
S2—Ni1—O2—C1223.8 (5)C12—N3—C11—S217.7 (9)
C9—N2—C1—N10.1 (9)Ni1—S2—C11—N4168.2 (4)
C10—N2—C1—N1178.9 (6)Ni1—S2—C11—N314.8 (6)
C9—N2—C1—S1179.8 (5)Ni1—O2—C12—N330.3 (10)
C10—N2—C1—S11.3 (8)Ni1—O2—C12—C13149.2 (4)
C2—N1—C1—N2179.8 (6)C11—N3—C12—O25.4 (10)
C2—N1—C1—S10.1 (9)C11—N3—C12—C13174.0 (5)
Ni1—S1—C1—N2179.0 (4)O2—C12—C13—C18147.9 (6)
Ni1—S1—C1—N10.8 (6)N3—C12—C13—C1832.6 (9)
Ni1—O1—C2—N11.0 (11)O2—C12—C13—C1430.6 (8)
Ni1—O1—C2—C3174.5 (4)N3—C12—C13—C14148.9 (6)
C1—N1—C2—O11.0 (11)C18—C13—C14—C151.8 (9)
C1—N1—C2—C3174.5 (5)C12—C13—C14—C15179.6 (6)
O1—C2—C3—C4121.4 (6)C13—C14—C15—C161.3 (10)
N1—C2—C3—C454.9 (8)C14—C15—C16—C171.2 (10)
O1—C2—C3—C856.1 (8)C15—C16—C17—C183.1 (10)
N1—C2—C3—C8127.6 (6)C16—C17—C18—C132.5 (10)
C8—C3—C4—C51.0 (9)C16—C17—C18—Cl2178.9 (5)
C2—C3—C4—C5176.6 (6)C14—C13—C18—C170.1 (9)
C3—C4—C5—C60.5 (10)C12—C13—C18—C17178.3 (6)
C4—C5—C6—C70.6 (10)C14—C13—C18—Cl2178.7 (4)
C5—C6—C7—C81.1 (9)C12—C13—C18—Cl20.2 (9)
 

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