Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803017069/cv6215sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803017069/cv6215Isup2.hkl |
CCDC reference: 188936
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.
H atoms were placed at calculated positions, riding on their parent C atoms, with isotropic displacement parameters Uiso(H) = 1.2Ueq(C).
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.
[Ni(C20H14ClN2OS)2]·CH2Cl2 | Z = 2 |
Mr = 875.32 | F(000) = 896 |
Triclinic, P1 | Dx = 1.500 Mg m−3 |
a = 8.4277 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.2923 (11) Å | Cell parameters from 1694 reflections |
c = 17.4582 (13) Å | θ = 2.5–23.3° |
α = 103.671 (2)° | µ = 0.93 mm−1 |
β = 98.230 (2)° | T = 173 K |
γ = 103.877 (2)° | Prism, red |
V = 1938.6 (3) Å3 | 0.20 × 0.18 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 7764 independent reflections |
Radiation source: sealed tube | 4564 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→10 |
Tmin = 0.818, Tmax = 0.912 | k = −14→17 |
11475 measured reflections | l = −21→21 |
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)] = 0.043 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.063 | H-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 parameters | Δρmax = 0.48 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
[Ni(C20H14ClN2OS)2]·CH2Cl2 | γ = 103.877 (2)° |
Mr = 875.32 | V = 1938.6 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.4277 (7) Å | Mo Kα radiation |
b = 14.2923 (11) Å | µ = 0.93 mm−1 |
c = 17.4582 (13) Å | T = 173 K |
α = 103.671 (2)° | 0.20 × 0.18 × 0.10 mm |
β = 98.230 (2)° |
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 = 0.912 | Rint = 0.038 |
11475 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.063 | H-atom parameters constrained |
S = 0.81 | Δρmax = 0.48 e Å−3 |
7764 reflections | Δρmin = −0.37 e Å−3 |
487 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.22140 (5) | 0.52946 (3) | 0.24514 (2) | 0.02097 (11) | |
Cl1 | 0.72290 (11) | 0.89841 (6) | 0.35893 (6) | 0.0369 (2) | |
Cl2 | −0.17912 (13) | 0.67009 (7) | 0.23857 (5) | 0.0488 (3) | |
S1 | 0.43380 (10) | 0.50547 (6) | 0.31210 (5) | 0.0257 (2) | |
S2 | 0.13324 (10) | 0.36949 (6) | 0.19730 (5) | 0.0237 (2) | |
O1 | 0.2875 (3) | 0.66783 (14) | 0.29061 (12) | 0.0277 (6) | |
O2 | 0.0476 (3) | 0.55418 (15) | 0.18198 (13) | 0.0306 (6) | |
N1 | 0.5224 (3) | 0.70780 (17) | 0.39525 (14) | 0.0193 (6) | |
N2 | 0.6753 (3) | 0.61125 (18) | 0.43621 (14) | 0.0192 (6) | |
N3 | −0.1095 (3) | 0.40061 (18) | 0.08882 (14) | 0.0185 (6) | |
N4 | −0.0811 (3) | 0.24425 (18) | 0.07052 (15) | 0.0211 (6) | |
C1 | 0.5332 (4) | 0.9151 (2) | 0.37815 (18) | 0.0230 (8) | |
C2 | 0.5208 (4) | 1.0123 (2) | 0.39830 (19) | 0.0314 (9) | |
H2A | 0.6158 | 1.0674 | 0.4050 | 0.038* | |
C3 | 0.3690 (5) | 1.0285 (3) | 0.4085 (2) | 0.0358 (9) | |
H3B | 0.3598 | 1.0951 | 0.4238 | 0.043* | |
C4 | 0.2314 (5) | 0.9480 (3) | 0.3966 (2) | 0.0382 (10) | |
H4A | 0.1263 | 0.9588 | 0.4023 | 0.046* | |
C5 | 0.2459 (4) | 0.8514 (2) | 0.37627 (19) | 0.0283 (9) | |
H5A | 0.1496 | 0.7963 | 0.3675 | 0.034* | |
C6 | 0.3972 (4) | 0.8330 (2) | 0.36846 (17) | 0.0199 (8) | |
C7 | 0.4031 (4) | 0.7263 (2) | 0.34818 (18) | 0.0193 (7) | |
C8 | 0.5456 (4) | 0.6167 (2) | 0.38337 (18) | 0.0189 (7) | |
C9 | 0.7299 (4) | 0.5213 (2) | 0.42885 (18) | 0.0180 (7) | |
C10 | 0.8301 (4) | 0.4997 (2) | 0.3758 (2) | 0.0313 (9) | |
H10A | 0.8597 | 0.5420 | 0.3426 | 0.038* | |
C11 | 0.8877 (4) | 0.4166 (3) | 0.3708 (2) | 0.0357 (10) | |
H11A | 0.9564 | 0.4011 | 0.3338 | 0.043* | |
C12 | 0.8453 (4) | 0.3561 (2) | 0.4196 (2) | 0.0334 (9) | |
H12A | 0.8841 | 0.2984 | 0.4161 | 0.040* | |
C13 | 0.7481 (4) | 0.3786 (2) | 0.4730 (2) | 0.0366 (10) | |
H13A | 0.7202 | 0.3367 | 0.5069 | 0.044* | |
C14 | 0.6895 (4) | 0.4618 (2) | 0.4785 (2) | 0.0292 (9) | |
H14A | 0.6221 | 0.4777 | 0.5161 | 0.035* | |
C15 | 0.7756 (4) | 0.6997 (2) | 0.50020 (19) | 0.0189 (7) | |
C16 | 0.7608 (4) | 0.7058 (2) | 0.57851 (19) | 0.0278 (8) | |
H16A | 0.6813 | 0.6548 | 0.5905 | 0.033* | |
C17 | 0.8644 (4) | 0.7881 (2) | 0.63985 (19) | 0.0293 (9) | |
H17A | 0.8555 | 0.7935 | 0.6943 | 0.035* | |
C18 | 0.9792 (4) | 0.8615 (2) | 0.62222 (19) | 0.0272 (8) | |
H18A | 1.0500 | 0.9173 | 0.6644 | 0.033* | |
C19 | 0.9917 (4) | 0.8542 (2) | 0.5436 (2) | 0.0262 (8) | |
H19A | 1.0699 | 0.9055 | 0.5313 | 0.031* | |
C20 | 0.8909 (4) | 0.7725 (2) | 0.48265 (19) | 0.0246 (8) | |
H20A | 0.9015 | 0.7666 | 0.4284 | 0.030* | |
C21 | −0.2322 (4) | 0.6294 (2) | 0.13403 (19) | 0.0271 (8) | |
C22 | −0.3331 (4) | 0.6763 (2) | 0.0967 (2) | 0.0375 (10) | |
H22A | −0.3668 | 0.7290 | 0.1282 | 0.045* | |
C23 | −0.3840 (4) | 0.6471 (3) | 0.0149 (2) | 0.0387 (10) | |
H23A | −0.4510 | 0.6807 | −0.0103 | 0.046* | |
C24 | −0.3391 (4) | 0.5688 (3) | −0.0320 (2) | 0.0310 (9) | |
H24A | −0.3751 | 0.5484 | −0.0890 | 0.037* | |
C25 | −0.2409 (4) | 0.5211 (2) | 0.00581 (19) | 0.0256 (8) | |
H25A | −0.2114 | 0.4667 | −0.0260 | 0.031* | |
C26 | −0.1845 (4) | 0.5504 (2) | 0.08888 (19) | 0.0213 (8) | |
C27 | −0.0718 (4) | 0.4983 (2) | 0.12550 (19) | 0.0205 (8) | |
C28 | −0.0267 (4) | 0.3419 (2) | 0.11511 (18) | 0.0180 (7) | |
C29 | −0.2027 (4) | 0.2116 (2) | −0.00486 (19) | 0.0207 (8) | |
C30 | −0.1630 (4) | 0.2449 (2) | −0.0693 (2) | 0.0307 (9) | |
H30A | −0.0581 | 0.2920 | −0.0637 | 0.037* | |
C31 | −0.2770 (5) | 0.2095 (3) | −0.1424 (2) | 0.0415 (10) | |
H31A | −0.2508 | 0.2329 | −0.1870 | 0.050* | |
C32 | −0.4286 (5) | 0.1404 (3) | −0.1505 (2) | 0.0424 (11) | |
H32A | −0.5059 | 0.1155 | −0.2010 | 0.051* | |
C33 | −0.4675 (4) | 0.1078 (2) | −0.0867 (2) | 0.0376 (10) | |
H33A | −0.5723 | 0.0605 | −0.0927 | 0.045* | |
C34 | −0.3554 (4) | 0.1430 (2) | −0.0128 (2) | 0.0279 (9) | |
H34A | −0.3832 | 0.1203 | 0.0318 | 0.033* | |
C35 | −0.0105 (4) | 0.1682 (2) | 0.09150 (18) | 0.0214 (8) | |
C36 | 0.1211 (4) | 0.1481 (2) | 0.0589 (2) | 0.0306 (9) | |
H36A | 0.1667 | 0.1847 | 0.0244 | 0.037* | |
C37 | 0.1857 (4) | 0.0744 (3) | 0.0767 (2) | 0.0418 (10) | |
H37A | 0.2784 | 0.0613 | 0.0556 | 0.050* | |
C38 | 0.1180 (5) | 0.0198 (3) | 0.1246 (2) | 0.0432 (11) | |
H38A | 0.1628 | −0.0317 | 0.1359 | 0.052* | |
C39 | −0.0153 (5) | 0.0390 (2) | 0.1569 (2) | 0.0398 (10) | |
H39A | −0.0624 | 0.0009 | 0.1901 | 0.048* | |
C40 | −0.0802 (4) | 0.1149 (2) | 0.14009 (18) | 0.0293 (9) | |
H40A | −0.1714 | 0.1293 | 0.1620 | 0.035* | |
C100 | 0.4973 (4) | 1.2590 (2) | 0.24215 (19) | 0.0356 (9) | |
H10B | 0.3751 | 1.2448 | 0.2235 | 0.043* | |
H10C | 0.5313 | 1.3102 | 0.2953 | 0.043* | |
Cl11 | 0.54216 (14) | 1.14915 (7) | 0.25308 (7) | 0.0600 (3) | |
Cl12 | 0.59950 (12) | 1.30724 (7) | 0.17371 (6) | 0.0476 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0201 (3) | 0.0150 (2) | 0.0216 (3) | 0.00395 (19) | −0.0052 (2) | 0.00037 (18) |
Cl1 | 0.0225 (5) | 0.0267 (5) | 0.0579 (7) | 0.0027 (4) | 0.0023 (5) | 0.0132 (5) |
Cl2 | 0.0661 (8) | 0.0489 (7) | 0.0311 (6) | 0.0330 (6) | 0.0010 (5) | −0.0007 (5) |
S1 | 0.0234 (5) | 0.0168 (5) | 0.0286 (5) | 0.0057 (4) | −0.0086 (4) | −0.0007 (4) |
S2 | 0.0230 (5) | 0.0168 (5) | 0.0242 (5) | 0.0039 (4) | −0.0065 (4) | 0.0009 (4) |
O1 | 0.0255 (14) | 0.0156 (13) | 0.0315 (15) | 0.0034 (11) | −0.0128 (11) | 0.0007 (10) |
O2 | 0.0272 (15) | 0.0157 (13) | 0.0358 (16) | 0.0037 (11) | −0.0147 (12) | −0.0022 (11) |
N1 | 0.0184 (16) | 0.0150 (15) | 0.0210 (16) | 0.0035 (12) | −0.0015 (13) | 0.0035 (12) |
N2 | 0.0174 (16) | 0.0164 (15) | 0.0194 (16) | 0.0035 (12) | −0.0028 (13) | 0.0025 (12) |
N3 | 0.0202 (16) | 0.0145 (15) | 0.0176 (15) | 0.0048 (12) | −0.0023 (12) | 0.0021 (12) |
N4 | 0.0233 (17) | 0.0146 (15) | 0.0203 (16) | 0.0041 (13) | −0.0016 (13) | 0.0003 (12) |
C1 | 0.025 (2) | 0.0186 (19) | 0.022 (2) | 0.0048 (16) | −0.0037 (16) | 0.0058 (15) |
C2 | 0.034 (2) | 0.017 (2) | 0.035 (2) | 0.0036 (17) | −0.0093 (18) | 0.0062 (16) |
C3 | 0.050 (3) | 0.021 (2) | 0.035 (2) | 0.015 (2) | 0.000 (2) | 0.0043 (17) |
C4 | 0.040 (3) | 0.036 (2) | 0.046 (3) | 0.024 (2) | 0.010 (2) | 0.013 (2) |
C5 | 0.027 (2) | 0.019 (2) | 0.038 (2) | 0.0074 (17) | 0.0057 (18) | 0.0064 (17) |
C6 | 0.023 (2) | 0.0173 (19) | 0.0161 (19) | 0.0064 (16) | −0.0024 (15) | 0.0022 (14) |
C7 | 0.021 (2) | 0.0173 (19) | 0.0153 (19) | 0.0026 (15) | 0.0043 (16) | −0.0008 (14) |
C8 | 0.0162 (19) | 0.0217 (19) | 0.0168 (19) | 0.0022 (15) | 0.0035 (15) | 0.0050 (15) |
C9 | 0.0124 (18) | 0.0151 (18) | 0.0206 (19) | 0.0021 (14) | −0.0065 (15) | 0.0015 (15) |
C10 | 0.037 (2) | 0.025 (2) | 0.034 (2) | 0.0106 (18) | 0.0082 (19) | 0.0098 (17) |
C11 | 0.041 (3) | 0.039 (3) | 0.030 (2) | 0.020 (2) | 0.010 (2) | 0.0041 (19) |
C12 | 0.029 (2) | 0.031 (2) | 0.037 (2) | 0.0146 (18) | −0.0061 (19) | 0.0047 (18) |
C13 | 0.042 (3) | 0.034 (2) | 0.042 (3) | 0.017 (2) | 0.008 (2) | 0.0189 (19) |
C14 | 0.026 (2) | 0.028 (2) | 0.038 (2) | 0.0111 (17) | 0.0114 (18) | 0.0116 (18) |
C15 | 0.0160 (19) | 0.0175 (19) | 0.020 (2) | 0.0058 (15) | −0.0027 (15) | 0.0028 (15) |
C16 | 0.029 (2) | 0.019 (2) | 0.028 (2) | −0.0027 (16) | 0.0034 (18) | 0.0037 (16) |
C17 | 0.032 (2) | 0.034 (2) | 0.019 (2) | 0.0081 (18) | 0.0041 (17) | 0.0035 (17) |
C18 | 0.025 (2) | 0.019 (2) | 0.027 (2) | 0.0031 (16) | −0.0038 (17) | −0.0019 (16) |
C19 | 0.023 (2) | 0.021 (2) | 0.028 (2) | −0.0007 (16) | −0.0029 (17) | 0.0069 (16) |
C20 | 0.025 (2) | 0.026 (2) | 0.020 (2) | 0.0036 (16) | 0.0004 (17) | 0.0077 (16) |
C21 | 0.030 (2) | 0.024 (2) | 0.027 (2) | 0.0084 (17) | 0.0016 (17) | 0.0085 (16) |
C22 | 0.038 (3) | 0.029 (2) | 0.049 (3) | 0.0159 (19) | 0.005 (2) | 0.013 (2) |
C23 | 0.032 (2) | 0.041 (3) | 0.051 (3) | 0.011 (2) | 0.001 (2) | 0.030 (2) |
C24 | 0.023 (2) | 0.043 (2) | 0.025 (2) | 0.0014 (18) | −0.0015 (17) | 0.0172 (18) |
C25 | 0.021 (2) | 0.026 (2) | 0.027 (2) | 0.0017 (16) | 0.0013 (17) | 0.0086 (16) |
C26 | 0.0157 (19) | 0.0180 (19) | 0.026 (2) | −0.0010 (15) | −0.0018 (16) | 0.0069 (15) |
C27 | 0.020 (2) | 0.023 (2) | 0.019 (2) | 0.0074 (16) | 0.0049 (16) | 0.0058 (15) |
C28 | 0.0207 (19) | 0.0154 (18) | 0.0157 (18) | 0.0012 (15) | 0.0050 (15) | 0.0038 (14) |
C29 | 0.025 (2) | 0.0103 (18) | 0.022 (2) | 0.0063 (15) | −0.0034 (16) | −0.0021 (14) |
C30 | 0.037 (2) | 0.019 (2) | 0.031 (2) | 0.0044 (17) | 0.0013 (19) | 0.0045 (17) |
C31 | 0.069 (3) | 0.035 (2) | 0.024 (2) | 0.024 (2) | 0.001 (2) | 0.0100 (18) |
C32 | 0.047 (3) | 0.037 (3) | 0.030 (2) | 0.019 (2) | −0.021 (2) | −0.0038 (19) |
C33 | 0.025 (2) | 0.033 (2) | 0.040 (3) | 0.0042 (18) | −0.0089 (19) | −0.0010 (19) |
C34 | 0.027 (2) | 0.026 (2) | 0.029 (2) | 0.0075 (17) | 0.0016 (18) | 0.0078 (17) |
C35 | 0.023 (2) | 0.0127 (18) | 0.0188 (19) | 0.0031 (15) | −0.0089 (16) | −0.0032 (14) |
C36 | 0.030 (2) | 0.022 (2) | 0.034 (2) | 0.0060 (17) | −0.0010 (18) | 0.0026 (16) |
C37 | 0.032 (2) | 0.030 (2) | 0.055 (3) | 0.013 (2) | −0.001 (2) | −0.001 (2) |
C38 | 0.055 (3) | 0.022 (2) | 0.039 (3) | 0.016 (2) | −0.022 (2) | −0.0040 (18) |
C39 | 0.063 (3) | 0.021 (2) | 0.028 (2) | 0.007 (2) | −0.004 (2) | 0.0055 (17) |
C40 | 0.038 (2) | 0.024 (2) | 0.020 (2) | 0.0074 (18) | −0.0006 (17) | 0.0000 (16) |
C100 | 0.037 (2) | 0.040 (2) | 0.031 (2) | 0.0136 (19) | 0.0085 (19) | 0.0097 (18) |
Cl11 | 0.0673 (8) | 0.0436 (7) | 0.0697 (8) | 0.0185 (6) | 0.0023 (7) | 0.0217 (6) |
Cl12 | 0.0500 (7) | 0.0565 (7) | 0.0377 (6) | 0.0138 (5) | 0.0122 (5) | 0.0153 (5) |
Ni1—O1 | 1.859 (2) | C16—H16A | 0.9500 |
Ni1—O2 | 1.859 (2) | C17—C18 | 1.372 (4) |
Ni1—S1 | 2.1384 (9) | C17—H17A | 0.9500 |
Ni1—S2 | 2.1405 (9) | C18—C19 | 1.372 (4) |
Cl1—C1 | 1.739 (3) | C18—H18A | 0.9500 |
Cl2—C21 | 1.735 (3) | C19—C20 | 1.377 (4) |
S1—C8 | 1.725 (3) | C19—H19A | 0.9500 |
S2—C28 | 1.719 (3) | C20—H20A | 0.9500 |
O1—C7 | 1.261 (3) | C21—C22 | 1.386 (4) |
O2—C27 | 1.258 (4) | C21—C26 | 1.395 (4) |
N1—C7 | 1.323 (3) | C22—C23 | 1.360 (4) |
N1—C8 | 1.335 (3) | C22—H22A | 0.9500 |
N2—C8 | 1.356 (3) | C23—C24 | 1.387 (4) |
N2—C9 | 1.450 (3) | C23—H23A | 0.9500 |
N2—C15 | 1.452 (4) | C24—C25 | 1.383 (4) |
N3—C27 | 1.329 (3) | C24—H24A | 0.9500 |
N3—C28 | 1.332 (3) | C25—C26 | 1.387 (4) |
N4—C28 | 1.357 (3) | C25—H25A | 0.9500 |
N4—C29 | 1.447 (4) | C26—C27 | 1.502 (4) |
N4—C35 | 1.451 (3) | C29—C30 | 1.374 (4) |
C1—C2 | 1.383 (4) | C29—C34 | 1.385 (4) |
C1—C6 | 1.387 (4) | C30—C31 | 1.385 (4) |
C2—C3 | 1.382 (4) | C30—H30A | 0.9500 |
C2—H2A | 0.9500 | C31—C32 | 1.380 (5) |
C3—C4 | 1.375 (4) | C31—H31A | 0.9500 |
C3—H3B | 0.9500 | C32—C33 | 1.357 (4) |
C4—C5 | 1.382 (4) | C32—H32A | 0.9500 |
C4—H4A | 0.9500 | C33—C34 | 1.388 (4) |
C5—C6 | 1.381 (4) | C33—H33A | 0.9500 |
C5—H5A | 0.9500 | C34—H34A | 0.9500 |
C6—C7 | 1.496 (4) | C35—C40 | 1.371 (4) |
C9—C10 | 1.370 (4) | C35—C36 | 1.376 (4) |
C9—C14 | 1.372 (4) | C36—C37 | 1.372 (4) |
C10—C11 | 1.376 (4) | C36—H36A | 0.9500 |
C10—H10A | 0.9500 | C37—C38 | 1.366 (4) |
C11—C12 | 1.374 (4) | C37—H37A | 0.9500 |
C11—H11A | 0.9500 | C38—C39 | 1.382 (4) |
C12—C13 | 1.358 (4) | C38—H38A | 0.9500 |
C12—H12A | 0.9500 | C39—C40 | 1.396 (4) |
C13—C14 | 1.383 (4) | C39—H39A | 0.9500 |
C13—H13A | 0.9500 | C40—H40A | 0.9500 |
C14—H14A | 0.9500 | C100—Cl12 | 1.745 (3) |
C15—C20 | 1.368 (4) | C100—Cl11 | 1.747 (3) |
C15—C16 | 1.375 (4) | C100—H10B | 0.9900 |
C16—C17 | 1.392 (4) | C100—H10C | 0.9900 |
O1—Ni1—O2 | 84.04 (9) | C18—C19—C20 | 120.0 (3) |
O1—Ni1—S1 | 94.83 (7) | C18—C19—H19A | 120.0 |
O2—Ni1—S1 | 175.54 (8) | C20—C19—H19A | 120.0 |
O1—Ni1—S2 | 176.33 (7) | C15—C20—C19 | 120.0 (3) |
O2—Ni1—S2 | 95.15 (7) | C15—C20—H20A | 120.0 |
S1—Ni1—S2 | 86.24 (3) | C19—C20—H20A | 120.0 |
C8—S1—Ni1 | 108.58 (11) | C22—C21—C26 | 120.7 (3) |
C28—S2—Ni1 | 107.82 (10) | C22—C21—Cl2 | 116.4 (3) |
C7—O1—Ni1 | 133.1 (2) | C26—C21—Cl2 | 122.8 (2) |
C27—O2—Ni1 | 132.9 (2) | C23—C22—C21 | 120.2 (3) |
C7—N1—C8 | 122.3 (3) | C23—C22—H22A | 119.9 |
C8—N2—C9 | 122.9 (3) | C21—C22—H22A | 119.9 |
C8—N2—C15 | 120.5 (2) | C22—C23—C24 | 120.8 (3) |
C9—N2—C15 | 116.5 (2) | C22—C23—H23A | 119.6 |
C27—N3—C28 | 121.9 (3) | C24—C23—H23A | 119.6 |
C28—N4—C29 | 121.7 (2) | C25—C24—C23 | 118.8 (3) |
C28—N4—C35 | 122.2 (3) | C25—C24—H24A | 120.6 |
C29—N4—C35 | 115.9 (2) | C23—C24—H24A | 120.6 |
C2—C1—C6 | 121.7 (3) | C24—C25—C26 | 121.8 (3) |
C2—C1—Cl1 | 117.5 (3) | C24—C25—H25A | 119.1 |
C6—C1—Cl1 | 120.7 (2) | C26—C25—H25A | 119.1 |
C3—C2—C1 | 119.5 (3) | C25—C26—C21 | 117.8 (3) |
C3—C2—H2A | 120.3 | C25—C26—C27 | 118.9 (3) |
C1—C2—H2A | 120.3 | C21—C26—C27 | 123.3 (3) |
C4—C3—C2 | 119.7 (3) | O2—C27—N3 | 130.5 (3) |
C4—C3—H3B | 120.2 | O2—C27—C26 | 115.6 (3) |
C2—C3—H3B | 120.2 | N3—C27—C26 | 113.8 (3) |
C3—C4—C5 | 120.1 (3) | N3—C28—N4 | 114.2 (3) |
C3—C4—H4A | 120.0 | N3—C28—S2 | 130.4 (2) |
C5—C4—H4A | 120.0 | N4—C28—S2 | 115.4 (2) |
C6—C5—C4 | 121.5 (3) | C30—C29—C34 | 120.3 (3) |
C6—C5—H5A | 119.3 | C30—C29—N4 | 119.9 (3) |
C4—C5—H5A | 119.3 | C34—C29—N4 | 119.7 (3) |
C5—C6—C1 | 117.5 (3) | C29—C30—C31 | 119.6 (3) |
C5—C6—C7 | 118.2 (3) | C29—C30—H30A | 120.2 |
C1—C6—C7 | 124.3 (3) | C31—C30—H30A | 120.2 |
O1—C7—N1 | 130.6 (3) | C32—C31—C30 | 120.1 (3) |
O1—C7—C6 | 113.8 (3) | C32—C31—H31A | 119.9 |
N1—C7—C6 | 115.5 (3) | C30—C31—H31A | 119.9 |
N1—C8—N2 | 114.7 (3) | C33—C32—C31 | 120.2 (4) |
N1—C8—S1 | 129.7 (2) | C33—C32—H32A | 119.9 |
N2—C8—S1 | 115.6 (2) | C31—C32—H32A | 119.9 |
C10—C9—C14 | 120.4 (3) | C32—C33—C34 | 120.6 (3) |
C10—C9—N2 | 119.7 (3) | C32—C33—H33A | 119.7 |
C14—C9—N2 | 119.7 (3) | C34—C33—H33A | 119.7 |
C9—C10—C11 | 120.0 (3) | C29—C34—C33 | 119.2 (3) |
C9—C10—H10A | 120.0 | C29—C34—H34A | 120.4 |
C11—C10—H10A | 120.0 | C33—C34—H34A | 120.4 |
C12—C11—C10 | 119.6 (3) | C40—C35—C36 | 121.3 (3) |
C12—C11—H11A | 120.2 | C40—C35—N4 | 119.8 (3) |
C10—C11—H11A | 120.2 | C36—C35—N4 | 118.8 (3) |
C13—C12—C11 | 120.3 (3) | C37—C36—C35 | 119.2 (3) |
C13—C12—H12A | 119.9 | C37—C36—H36A | 120.4 |
C11—C12—H12A | 119.9 | C35—C36—H36A | 120.4 |
C12—C13—C14 | 120.6 (3) | C38—C37—C36 | 120.7 (3) |
C12—C13—H13A | 119.7 | C38—C37—H37A | 119.7 |
C14—C13—H13A | 119.7 | C36—C37—H37A | 119.7 |
C9—C14—C13 | 119.1 (3) | C37—C38—C39 | 120.4 (3) |
C9—C14—H14A | 120.5 | C37—C38—H38A | 119.8 |
C13—C14—H14A | 120.5 | C39—C38—H38A | 119.8 |
C20—C15—C16 | 120.8 (3) | C38—C39—C40 | 119.4 (3) |
C20—C15—N2 | 119.8 (3) | C38—C39—H39A | 120.3 |
C16—C15—N2 | 119.3 (3) | C40—C39—H39A | 120.3 |
C15—C16—C17 | 118.8 (3) | C35—C40—C39 | 119.0 (3) |
C15—C16—H16A | 120.6 | C35—C40—H40A | 120.5 |
C17—C16—H16A | 120.6 | C39—C40—H40A | 120.5 |
C18—C17—C16 | 120.4 (3) | Cl12—C100—Cl11 | 112.29 (17) |
C18—C17—H17A | 119.8 | Cl12—C100—H10B | 109.1 |
C16—C17—H17A | 119.8 | Cl11—C100—H10B | 109.1 |
C17—C18—C19 | 120.0 (3) | Cl12—C100—H10C | 109.1 |
C17—C18—H18A | 120.0 | Cl11—C100—H10C | 109.1 |
C19—C18—H18A | 120.0 | H10B—C100—H10C | 107.9 |
O1—Ni1—S1—C8 | 8.05 (12) | C17—C18—C19—C20 | −1.1 (5) |
S2—Ni1—S1—C8 | −168.43 (11) | C16—C15—C20—C19 | −1.3 (5) |
O2—Ni1—S2—C28 | 10.04 (13) | N2—C15—C20—C19 | −177.0 (3) |
S1—Ni1—S2—C28 | −165.71 (11) | C18—C19—C20—C15 | 1.5 (5) |
O2—Ni1—O1—C7 | 175.8 (3) | C26—C21—C22—C23 | −1.4 (5) |
S1—Ni1—O1—C7 | −8.6 (3) | Cl2—C21—C22—C23 | −178.3 (3) |
O1—Ni1—O2—C27 | 177.7 (3) | C21—C22—C23—C24 | 1.4 (5) |
S2—Ni1—O2—C27 | −5.9 (3) | C22—C23—C24—C25 | −0.2 (5) |
C6—C1—C2—C3 | −0.5 (5) | C23—C24—C25—C26 | −1.0 (5) |
Cl1—C1—C2—C3 | 175.5 (3) | C24—C25—C26—C21 | 1.0 (5) |
C1—C2—C3—C4 | −1.7 (5) | C24—C25—C26—C27 | −177.2 (3) |
C2—C3—C4—C5 | 1.5 (5) | C22—C21—C26—C25 | 0.2 (5) |
C3—C4—C5—C6 | 0.8 (5) | Cl2—C21—C26—C25 | 176.9 (2) |
C4—C5—C6—C1 | −2.9 (5) | C22—C21—C26—C27 | 178.3 (3) |
C4—C5—C6—C7 | 178.6 (3) | Cl2—C21—C26—C27 | −4.9 (5) |
C2—C1—C6—C5 | 2.7 (5) | Ni1—O2—C27—N3 | −3.7 (5) |
Cl1—C1—C6—C5 | −173.1 (2) | Ni1—O2—C27—C26 | −178.69 (19) |
C2—C1—C6—C7 | −178.9 (3) | C28—N3—C27—O2 | 7.5 (5) |
Cl1—C1—C6—C7 | 5.3 (4) | C28—N3—C27—C26 | −177.4 (3) |
Ni1—O1—C7—N1 | 2.3 (5) | C25—C26—C27—O2 | 139.0 (3) |
Ni1—O1—C7—C6 | −174.18 (19) | C21—C26—C27—O2 | −39.1 (4) |
C8—N1—C7—O1 | 5.2 (5) | C25—C26—C27—N3 | −36.9 (4) |
C8—N1—C7—C6 | −178.4 (3) | C21—C26—C27—N3 | 145.0 (3) |
C5—C6—C7—O1 | 47.5 (4) | C27—N3—C28—N4 | −179.8 (3) |
C1—C6—C7—O1 | −130.9 (3) | C27—N3—C28—S2 | 2.0 (5) |
C5—C6—C7—N1 | −129.5 (3) | C29—N4—C28—N3 | 8.0 (4) |
C1—C6—C7—N1 | 52.1 (4) | C35—N4—C28—N3 | −177.6 (3) |
C7—N1—C8—N2 | 178.8 (3) | C29—N4—C28—S2 | −173.5 (2) |
C7—N1—C8—S1 | −2.2 (4) | C35—N4—C28—S2 | 0.9 (4) |
C9—N2—C8—N1 | −174.3 (2) | Ni1—S2—C28—N3 | −10.9 (3) |
C15—N2—C8—N1 | 0.8 (4) | Ni1—S2—C28—N4 | 170.91 (19) |
C9—N2—C8—S1 | 6.6 (4) | C28—N4—C29—C30 | 64.8 (4) |
C15—N2—C8—S1 | −178.4 (2) | C35—N4—C29—C30 | −109.9 (3) |
Ni1—S1—C8—N1 | −5.3 (3) | C28—N4—C29—C34 | −118.4 (3) |
Ni1—S1—C8—N2 | 173.65 (18) | C35—N4—C29—C34 | 66.9 (4) |
C8—N2—C9—C10 | 80.4 (4) | C34—C29—C30—C31 | 0.0 (5) |
C15—N2—C9—C10 | −94.8 (3) | N4—C29—C30—C31 | 176.9 (3) |
C8—N2—C9—C14 | −103.6 (3) | C29—C30—C31—C32 | −0.7 (5) |
C15—N2—C9—C14 | 81.2 (4) | C30—C31—C32—C33 | 0.9 (5) |
C14—C9—C10—C11 | 1.5 (5) | C31—C32—C33—C34 | −0.4 (5) |
N2—C9—C10—C11 | 177.5 (3) | C30—C29—C34—C33 | 0.4 (5) |
C9—C10—C11—C12 | −0.5 (5) | N4—C29—C34—C33 | −176.4 (3) |
C10—C11—C12—C13 | −0.5 (5) | C32—C33—C34—C29 | −0.3 (5) |
C11—C12—C13—C14 | 0.5 (5) | C28—N4—C35—C40 | 91.2 (4) |
C10—C9—C14—C13 | −1.4 (5) | C29—N4—C35—C40 | −94.1 (3) |
N2—C9—C14—C13 | −177.4 (3) | C28—N4—C35—C36 | −91.7 (4) |
C12—C13—C14—C9 | 0.4 (5) | C29—N4—C35—C36 | 82.9 (4) |
C8—N2—C15—C20 | −76.0 (4) | C40—C35—C36—C37 | −1.3 (5) |
C9—N2—C15—C20 | 99.3 (3) | N4—C35—C36—C37 | −178.3 (3) |
C8—N2—C15—C16 | 108.3 (3) | C35—C36—C37—C38 | 1.6 (5) |
C9—N2—C15—C16 | −76.4 (4) | C36—C37—C38—C39 | −0.9 (6) |
C20—C15—C16—C17 | 0.6 (5) | C37—C38—C39—C40 | −0.1 (5) |
N2—C15—C16—C17 | 176.3 (3) | C36—C35—C40—C39 | 0.3 (5) |
C15—C16—C17—C18 | −0.1 (5) | N4—C35—C40—C39 | 177.3 (3) |
C16—C17—C18—C19 | 0.4 (5) | C38—C39—C40—C35 | 0.4 (5) |
Experimental details
Crystal data | |
Chemical formula | [Ni(C20H14ClN2OS)2]·CH2Cl2 |
Mr | 875.32 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1938.6 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.93 |
Crystal size (mm) | 0.20 × 0.18 × 0.10 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.818, 0.912 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11475, 7764, 4564 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.063, 0.81 |
No. of reflections | 7764 |
No. of parameters | 487 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.48, −0.37 |
Computer programs: SMART (Bruker, 2002), SMART, SAINT (Bruker, 2002), SHELXTL (Bruker, 2002), SHELXTL.
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.