

Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808017145/hy2137sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536808017145/hy2137Isup2.hkl |
CCDC reference: 696426
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean
(C-C) = 0.012 Å
- R factor = 0.084
- wR factor = 0.131
- Data-to-parameter ratio = 11.0
checkCIF/PLATON results
No syntax errors found
Alert level C RINTA01_ALERT_3_C The value of Rint is greater than 0.10 Rint given 0.123 PLAT020_ALERT_3_C The value of Rint is greater than 0.10 ......... 0.12 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for S1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C43 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT341_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 12
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 5260 Count of symmetry unique reflns 3812 Completeness (_total/calc) 137.99% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1448 Fraction of Friedel pairs measured 0.380 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 0 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 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
N-benzoyl-N',N'-dibenzylthiourea ligand was synthesized according to a procedure described by Hernández et al. (2003), by converting benzoyl chloride into benzoyl isothiocyanate and then condensing with an appropriate amine. To an ethanol solution (30 ml) containing the ligand (0.96 g, 3 mmol) was added an ethanol solution of Ni(CH3COO)2.4H2O (0.25 g, 1 mmol). The solution was stirred at room temperature for 2 h, and at once a solution of NaOH (1 N) was added to adjust pH to the neutral value. The mixture was filtered and the filtrate was evaporated under reduced pressure to give a red solid, which was washed with acetone. Single crystals were obtained by slow evaporation of a chloroform/N,N-diphenylformamide solution (1:1, v/v) of the complex.
H atoms were positioned geometrically and refined as riding atoms, with C—H = 0.93 (aromatic) and 0.97 Å (methylene) and Uiso(H) = 1.2Ueq(C).
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
![]() | Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. |
![]() | Fig. 2. View of the unit cell of the title compound. |
[Ni(C22H19N2OS)2] | F(000) = 1624 |
Mr = 777.61 | Dx = 1.386 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 24585 reflections |
a = 5.5645 (1) Å | θ = 2.9–25.0° |
b = 19.7873 (7) Å | µ = 0.68 mm−1 |
c = 33.859 (1) Å | T = 294 K |
V = 3728.09 (18) Å3 | Needle, red |
Z = 4 | 0.34 × 0.05 × 0.04 mm |
Nonius KappaCCD diffractometer | 4302 reflections with I > 2σ(I) |
ϕ and ω scans | Rint = 0.123 |
Absorption correction: gaussian (Coppens et al., 1965) | θmax = 25.0°, θmin = 3.2° |
Tmin = 0.765, Tmax = 0.950 | h = −6→5 |
16007 measured reflections | k = −23→23 |
5260 independent reflections | l = −39→40 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + 5.999P] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.084 | (Δ/σ)max < 0.001 |
wR(F2) = 0.131 | Δρmax = 0.35 e Å−3 |
S = 1.17 | Δρmin = −0.48 e Å−3 |
5260 reflections | Absolute structure: Flack (1983), 1448 Friedel pairs |
479 parameters | Absolute structure parameter: 0.02 (3) |
0 restraints |
[Ni(C22H19N2OS)2] | V = 3728.09 (18) Å3 |
Mr = 777.61 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 5.5645 (1) Å | µ = 0.68 mm−1 |
b = 19.7873 (7) Å | T = 294 K |
c = 33.859 (1) Å | 0.34 × 0.05 × 0.04 mm |
Nonius KappaCCD diffractometer | 5260 independent reflections |
Absorption correction: gaussian (Coppens et al., 1965) | 4302 reflections with I > 2σ(I) |
Tmin = 0.765, Tmax = 0.950 | Rint = 0.123 |
16007 measured reflections |
R[F2 > 2σ(F2)] = 0.084 | H-atom parameters constrained |
wR(F2) = 0.131 | Δρmax = 0.35 e Å−3 |
S = 1.17 | Δρmin = −0.48 e Å−3 |
5260 reflections | Absolute structure: Flack (1983), 1448 Friedel pairs |
479 parameters | Absolute structure parameter: 0.02 (3) |
0 restraints |
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. |
x | y | z | Uiso*/Ueq | ||
Ni1 | 0.21477 (16) | 0.47548 (4) | 0.38022 (3) | 0.0437 (3) | |
S2 | −0.0611 (4) | 0.42371 (10) | 0.41155 (8) | 0.0582 (7) | |
S1 | 0.2840 (5) | 0.37861 (10) | 0.35445 (8) | 0.0694 (7) | |
N4 | −0.3836 (10) | 0.4556 (2) | 0.4654 (2) | 0.0395 (17) | |
O2 | 0.1541 (9) | 0.5590 (2) | 0.40168 (17) | 0.0502 (15) | |
N3 | −0.1887 (11) | 0.5475 (3) | 0.44201 (19) | 0.0417 (17) | |
N1 | 0.5878 (12) | 0.4449 (3) | 0.3040 (2) | 0.0445 (17) | |
O1 | 0.4633 (9) | 0.5193 (2) | 0.35422 (17) | 0.0544 (14) | |
C31 | −0.5155 (13) | 0.5008 (3) | 0.4918 (3) | 0.057 (2) | |
H31A | −0.6743 | 0.4821 | 0.4963 | 0.068* | |
H31B | −0.5356 | 0.5441 | 0.4787 | 0.068* | |
C24 | −0.2165 (13) | 0.4798 (4) | 0.4400 (2) | 0.0417 (18) | |
N2 | 0.4658 (12) | 0.3396 (3) | 0.2864 (2) | 0.0508 (18) | |
C3 | 0.7812 (14) | 0.5504 (4) | 0.3122 (2) | 0.046 (2) | |
C25 | −0.0194 (13) | 0.6554 (3) | 0.4309 (2) | 0.0383 (19) | |
C15 | 0.3589 (15) | 0.1551 (4) | 0.2963 (3) | 0.060 (2) | |
H15 | 0.2214 | 0.1514 | 0.2808 | 0.072* | |
C10 | 0.4474 (14) | 0.2178 (4) | 0.3044 (2) | 0.040 (2) | |
C9 | 0.3175 (14) | 0.2788 (3) | 0.2901 (3) | 0.050 (2) | |
H9A | 0.248 | 0.2687 | 0.2644 | 0.06* | |
H9B | 0.1862 | 0.2883 | 0.3081 | 0.06* | |
C16 | 0.6170 (14) | 0.3428 (4) | 0.2507 (3) | 0.054 (2) | |
H16A | 0.7059 | 0.301 | 0.2477 | 0.065* | |
H16B | 0.7316 | 0.3796 | 0.253 | 0.065* | |
C28 | −0.0128 (16) | 0.7928 (4) | 0.4458 (3) | 0.057 (3) | |
H28 | −0.0087 | 0.8388 | 0.4514 | 0.069* | |
C38 | −0.4472 (13) | 0.3833 (3) | 0.4672 (3) | 0.043 (2) | |
H38A | −0.3769 | 0.3603 | 0.4447 | 0.052* | |
H38B | −0.6204 | 0.3787 | 0.4654 | 0.052* | |
C1 | 0.5936 (14) | 0.5015 (4) | 0.3256 (3) | 0.045 (2) | |
C23 | −0.0152 (15) | 0.5805 (3) | 0.4229 (3) | 0.044 (2) | |
C37 | −0.1911 (14) | 0.5516 (3) | 0.5343 (3) | 0.049 (2) | |
H37 | −0.1324 | 0.5732 | 0.5119 | 0.059* | |
C5 | 1.1304 (15) | 0.5778 (4) | 0.2741 (3) | 0.066 (3) | |
H5 | 1.2477 | 0.5648 | 0.2561 | 0.079* | |
C42 | −0.2177 (17) | 0.2847 (4) | 0.5739 (3) | 0.061 (2) | |
H42 | −0.1689 | 0.2628 | 0.5968 | 0.073* | |
C43 | −0.4345 (18) | 0.2682 (4) | 0.5563 (3) | 0.070 (3) | |
H43 | −0.5341 | 0.2357 | 0.5676 | 0.084* | |
C32 | −0.3930 (13) | 0.5123 (3) | 0.5319 (3) | 0.047 (2) | |
C40 | −0.1427 (13) | 0.3649 (4) | 0.5220 (3) | 0.044 (2) | |
H40 | −0.0404 | 0.3959 | 0.51 | 0.052* | |
C26 | −0.2030 (14) | 0.6860 (3) | 0.4520 (2) | 0.050 (2) | |
H26 | −0.3296 | 0.66 | 0.4616 | 0.059* | |
C29 | 0.1682 (15) | 0.7645 (4) | 0.4247 (3) | 0.057 (2) | |
H29 | 0.2926 | 0.7913 | 0.4151 | 0.069* | |
C17 | 0.4570 (15) | 0.3541 (4) | 0.2150 (3) | 0.053 (2) | |
C2 | 0.4545 (14) | 0.3915 (4) | 0.3127 (2) | 0.043 (2) | |
C27 | −0.1995 (15) | 0.7549 (4) | 0.4590 (2) | 0.051 (2) | |
H27 | −0.3251 | 0.7752 | 0.4726 | 0.061* | |
C12 | 0.7559 (17) | 0.1644 (5) | 0.3434 (3) | 0.077 (3) | |
H12 | 0.8915 | 0.1677 | 0.3594 | 0.092* | |
C35 | −0.1550 (17) | 0.5270 (4) | 0.6035 (3) | 0.068 (3) | |
H35 | −0.0755 | 0.5322 | 0.6275 | 0.081* | |
C30 | 0.1670 (13) | 0.6960 (4) | 0.4175 (3) | 0.052 (2) | |
H30 | 0.2928 | 0.6767 | 0.4033 | 0.063* | |
C33 | −0.4729 (15) | 0.4803 (4) | 0.5658 (3) | 0.057 (2) | |
H33 | −0.6099 | 0.4534 | 0.5647 | 0.068* | |
C39 | −0.3608 (12) | 0.3498 (3) | 0.5050 (2) | 0.0347 (19) | |
C21 | 0.3153 (17) | 0.3233 (4) | 0.1501 (3) | 0.067 (3) | |
H21 | 0.3259 | 0.2953 | 0.1281 | 0.08* | |
C36 | −0.0719 (16) | 0.5593 (4) | 0.5708 (3) | 0.058 (2) | |
H36 | 0.064 | 0.5865 | 0.5725 | 0.069* | |
C8 | 0.7795 (16) | 0.6155 (4) | 0.3267 (3) | 0.064 (2) | |
H8 | 0.6612 | 0.6285 | 0.3445 | 0.077* | |
C4 | 0.9590 (14) | 0.5329 (4) | 0.2857 (3) | 0.053 (2) | |
H4 | 0.9619 | 0.4893 | 0.2755 | 0.064* | |
C20 | 0.1462 (16) | 0.3726 (5) | 0.1514 (3) | 0.070 (3) | |
H20 | 0.0407 | 0.3786 | 0.1304 | 0.084* | |
C18 | 0.2883 (17) | 0.4056 (4) | 0.2155 (3) | 0.070 (3) | |
H18 | 0.2795 | 0.4349 | 0.237 | 0.084* | |
C41 | −0.0754 (14) | 0.3336 (4) | 0.5573 (3) | 0.058 (2) | |
H41 | 0.0673 | 0.346 | 0.5696 | 0.07* | |
C44 | −0.5013 (13) | 0.3004 (4) | 0.5218 (3) | 0.048 (2) | |
H44 | −0.645 | 0.2884 | 0.5097 | 0.058* | |
C6 | 1.1298 (15) | 0.6425 (5) | 0.2892 (3) | 0.066 (3) | |
H6 | 1.2495 | 0.6728 | 0.2818 | 0.079* | |
C19 | 0.1326 (17) | 0.4131 (5) | 0.1839 (4) | 0.078 (3) | |
H19 | 0.0157 | 0.4467 | 0.1848 | 0.094* | |
C13 | 0.660 (2) | 0.1020 (5) | 0.3345 (4) | 0.085 (3) | |
H13 | 0.7277 | 0.0631 | 0.345 | 0.102* | |
C22 | 0.4738 (17) | 0.3145 (4) | 0.1816 (3) | 0.059 (3) | |
H22 | 0.5922 | 0.2814 | 0.1801 | 0.071* | |
C7 | 0.9547 (17) | 0.6622 (4) | 0.3148 (3) | 0.072 (3) | |
H7 | 0.9513 | 0.7063 | 0.3243 | 0.086* | |
C34 | −0.3522 (18) | 0.4875 (4) | 0.6014 (3) | 0.073 (3) | |
H34 | −0.4072 | 0.4652 | 0.6238 | 0.087* | |
C11 | 0.6491 (15) | 0.2218 (4) | 0.3286 (3) | 0.060 (3) | |
H11 | 0.7129 | 0.2639 | 0.3348 | 0.072* | |
C14 | 0.4646 (19) | 0.0972 (4) | 0.3101 (3) | 0.074 (3) | |
H14 | 0.4044 | 0.0551 | 0.3029 | 0.089* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0514 (6) | 0.0432 (5) | 0.0365 (6) | 0.0040 (5) | 0.0014 (5) | −0.0003 (5) |
S2 | 0.0683 (15) | 0.0418 (11) | 0.0645 (18) | 0.0003 (11) | 0.0191 (13) | −0.0026 (11) |
S1 | 0.1009 (19) | 0.0482 (12) | 0.0590 (17) | 0.0005 (13) | 0.0286 (16) | −0.0022 (11) |
N4 | 0.040 (4) | 0.028 (3) | 0.050 (5) | −0.002 (3) | 0.006 (3) | −0.001 (3) |
O2 | 0.051 (3) | 0.043 (3) | 0.057 (4) | 0.003 (2) | 0.018 (3) | 0.000 (3) |
N3 | 0.045 (4) | 0.032 (3) | 0.049 (5) | −0.005 (3) | −0.001 (4) | 0.000 (3) |
N1 | 0.051 (4) | 0.049 (4) | 0.033 (5) | −0.002 (3) | 0.002 (3) | −0.001 (4) |
O1 | 0.056 (3) | 0.056 (3) | 0.051 (4) | 0.001 (3) | 0.016 (3) | −0.010 (3) |
C31 | 0.044 (5) | 0.047 (5) | 0.079 (8) | 0.002 (4) | 0.017 (5) | −0.001 (5) |
C24 | 0.044 (4) | 0.044 (4) | 0.037 (5) | −0.002 (4) | −0.008 (4) | −0.006 (4) |
N2 | 0.064 (4) | 0.044 (4) | 0.044 (5) | −0.007 (4) | 0.002 (4) | −0.010 (4) |
C3 | 0.045 (5) | 0.049 (5) | 0.044 (6) | 0.000 (4) | −0.008 (5) | −0.004 (4) |
C25 | 0.039 (4) | 0.044 (4) | 0.032 (5) | −0.002 (4) | 0.000 (4) | −0.005 (4) |
C15 | 0.065 (6) | 0.059 (6) | 0.057 (7) | −0.002 (5) | 0.003 (5) | −0.008 (5) |
C10 | 0.039 (5) | 0.051 (5) | 0.030 (5) | −0.005 (4) | 0.015 (4) | −0.008 (4) |
C9 | 0.055 (5) | 0.045 (4) | 0.049 (6) | 0.005 (4) | −0.005 (4) | 0.001 (4) |
C16 | 0.057 (6) | 0.059 (5) | 0.046 (6) | 0.005 (4) | 0.016 (5) | −0.004 (5) |
C28 | 0.073 (6) | 0.041 (5) | 0.059 (7) | 0.003 (5) | −0.014 (5) | −0.009 (5) |
C38 | 0.031 (4) | 0.041 (4) | 0.057 (7) | −0.011 (3) | −0.004 (4) | 0.000 (4) |
C1 | 0.044 (5) | 0.040 (5) | 0.050 (6) | 0.002 (4) | −0.014 (5) | 0.010 (4) |
C23 | 0.058 (6) | 0.033 (4) | 0.040 (6) | −0.003 (4) | −0.014 (5) | −0.006 (4) |
C37 | 0.051 (5) | 0.040 (4) | 0.055 (6) | −0.008 (4) | 0.006 (5) | −0.001 (4) |
C5 | 0.054 (6) | 0.066 (6) | 0.078 (8) | −0.001 (5) | 0.020 (5) | −0.003 (6) |
C42 | 0.073 (6) | 0.050 (5) | 0.060 (7) | 0.010 (5) | −0.006 (6) | 0.010 (5) |
C43 | 0.069 (7) | 0.050 (6) | 0.090 (9) | −0.013 (5) | 0.004 (6) | 0.004 (6) |
C32 | 0.050 (5) | 0.035 (4) | 0.056 (6) | 0.006 (4) | 0.004 (4) | −0.007 (4) |
C40 | 0.042 (5) | 0.044 (5) | 0.044 (6) | 0.001 (4) | 0.008 (4) | −0.004 (4) |
C26 | 0.053 (5) | 0.048 (5) | 0.047 (6) | 0.004 (4) | 0.001 (5) | 0.008 (4) |
C29 | 0.064 (6) | 0.043 (5) | 0.064 (7) | −0.006 (4) | −0.003 (5) | 0.002 (4) |
C17 | 0.059 (5) | 0.044 (5) | 0.055 (7) | 0.006 (4) | 0.016 (5) | 0.000 (5) |
C2 | 0.055 (5) | 0.059 (5) | 0.016 (5) | 0.012 (4) | 0.008 (4) | −0.007 (4) |
C27 | 0.061 (5) | 0.050 (5) | 0.042 (6) | 0.001 (4) | 0.001 (5) | −0.001 (4) |
C12 | 0.069 (7) | 0.093 (7) | 0.068 (8) | 0.028 (7) | −0.003 (6) | 0.006 (6) |
C35 | 0.097 (7) | 0.054 (5) | 0.052 (7) | −0.002 (6) | 0.005 (5) | 0.006 (5) |
C30 | 0.048 (5) | 0.047 (5) | 0.062 (7) | 0.005 (4) | −0.002 (5) | 0.005 (4) |
C33 | 0.071 (6) | 0.056 (5) | 0.043 (6) | −0.014 (5) | 0.024 (5) | 0.000 (5) |
C39 | 0.035 (4) | 0.032 (4) | 0.038 (5) | 0.005 (3) | −0.006 (4) | −0.004 (4) |
C21 | 0.086 (7) | 0.073 (6) | 0.041 (6) | −0.003 (6) | −0.010 (6) | −0.011 (5) |
C36 | 0.055 (5) | 0.055 (5) | 0.063 (8) | −0.002 (4) | −0.001 (5) | −0.008 (5) |
C8 | 0.063 (6) | 0.068 (6) | 0.060 (7) | 0.004 (5) | 0.006 (5) | −0.005 (5) |
C4 | 0.056 (5) | 0.059 (5) | 0.045 (6) | 0.007 (5) | 0.016 (4) | −0.003 (5) |
C20 | 0.074 (7) | 0.078 (6) | 0.058 (8) | 0.010 (5) | −0.015 (6) | 0.016 (6) |
C18 | 0.091 (7) | 0.065 (6) | 0.052 (7) | 0.019 (6) | −0.007 (6) | −0.007 (5) |
C41 | 0.041 (5) | 0.070 (6) | 0.064 (8) | 0.008 (5) | −0.011 (5) | −0.003 (5) |
C44 | 0.037 (5) | 0.044 (4) | 0.064 (7) | −0.009 (4) | 0.003 (4) | 0.000 (5) |
C6 | 0.064 (6) | 0.070 (6) | 0.064 (8) | −0.012 (5) | 0.000 (5) | 0.006 (5) |
C19 | 0.092 (8) | 0.067 (6) | 0.076 (9) | 0.028 (5) | 0.004 (7) | −0.003 (6) |
C13 | 0.094 (9) | 0.075 (7) | 0.085 (9) | 0.013 (6) | 0.008 (7) | 0.025 (6) |
C22 | 0.083 (7) | 0.048 (5) | 0.047 (7) | 0.012 (5) | 0.005 (5) | −0.017 (5) |
C7 | 0.081 (7) | 0.056 (6) | 0.078 (9) | −0.013 (5) | 0.011 (6) | −0.016 (5) |
C34 | 0.115 (8) | 0.066 (6) | 0.037 (6) | −0.011 (6) | 0.013 (6) | 0.004 (5) |
C11 | 0.058 (6) | 0.067 (6) | 0.055 (7) | 0.004 (5) | 0.003 (5) | −0.009 (5) |
C14 | 0.086 (7) | 0.054 (6) | 0.083 (9) | −0.005 (6) | 0.001 (7) | 0.002 (6) |
Ni1—O2 | 1.837 (5) | C42—C41 | 1.370 (11) |
Ni1—O1 | 1.855 (5) | C42—C43 | 1.385 (12) |
Ni1—S2 | 2.128 (2) | C42—H42 | 0.93 |
Ni1—S1 | 2.141 (2) | C43—C44 | 1.382 (12) |
S2—C24 | 1.706 (7) | C43—H43 | 0.93 |
S1—C2 | 1.722 (8) | C32—C33 | 1.386 (11) |
N4—C24 | 1.353 (9) | C40—C39 | 1.376 (9) |
N4—C31 | 1.460 (9) | C40—C41 | 1.398 (11) |
N4—C38 | 1.474 (7) | C40—H40 | 0.93 |
O2—C23 | 1.259 (9) | C26—C27 | 1.384 (9) |
N3—C23 | 1.333 (10) | C26—H26 | 0.93 |
N3—C24 | 1.352 (8) | C29—C30 | 1.377 (10) |
N1—C2 | 1.326 (9) | C29—H29 | 0.93 |
N1—C1 | 1.338 (9) | C17—C22 | 1.378 (12) |
O1—C1 | 1.260 (9) | C17—C18 | 1.385 (10) |
C31—C32 | 1.536 (11) | C27—H27 | 0.93 |
C31—H31A | 0.97 | C12—C11 | 1.376 (11) |
C31—H31B | 0.97 | C12—C13 | 1.380 (12) |
N2—C2 | 1.359 (9) | C12—H12 | 0.93 |
N2—C9 | 1.464 (8) | C35—C34 | 1.348 (11) |
N2—C16 | 1.475 (10) | C35—C36 | 1.359 (12) |
C3—C4 | 1.378 (10) | C35—H35 | 0.93 |
C3—C8 | 1.379 (9) | C30—H30 | 0.93 |
C3—C1 | 1.495 (10) | C33—C34 | 1.388 (12) |
C25—C26 | 1.385 (10) | C33—H33 | 0.93 |
C25—C30 | 1.389 (10) | C39—C44 | 1.375 (10) |
C25—C23 | 1.506 (9) | C21—C20 | 1.355 (11) |
C15—C10 | 1.364 (10) | C21—C22 | 1.395 (12) |
C15—C14 | 1.369 (11) | C21—H21 | 0.93 |
C15—H15 | 0.93 | C36—H36 | 0.93 |
C10—C11 | 1.392 (11) | C8—C7 | 1.403 (11) |
C10—C9 | 1.488 (10) | C8—H8 | 0.93 |
C9—H9A | 0.97 | C4—H4 | 0.93 |
C9—H9B | 0.97 | C20—C19 | 1.363 (13) |
C16—C17 | 1.519 (11) | C20—H20 | 0.93 |
C16—H16A | 0.97 | C18—C19 | 1.386 (13) |
C16—H16B | 0.97 | C18—H18 | 0.93 |
C28—C27 | 1.356 (11) | C41—H41 | 0.93 |
C28—C29 | 1.356 (11) | C44—H44 | 0.93 |
C28—H28 | 0.93 | C6—C7 | 1.361 (12) |
C38—C39 | 1.518 (10) | C6—H6 | 0.93 |
C38—H38A | 0.97 | C19—H19 | 0.93 |
C38—H38B | 0.97 | C13—C14 | 1.366 (13) |
C37—C32 | 1.368 (10) | C13—H13 | 0.93 |
C37—C36 | 1.411 (12) | C22—H22 | 0.93 |
C37—H37 | 0.93 | C7—H7 | 0.93 |
C5—C4 | 1.360 (10) | C34—H34 | 0.93 |
C5—C6 | 1.378 (11) | C11—H11 | 0.93 |
C5—H5 | 0.93 | C14—H14 | 0.93 |
O2—Ni1—O1 | 84.5 (2) | C39—C40—C41 | 119.9 (7) |
O2—Ni1—S2 | 95.94 (17) | C39—C40—H40 | 120.1 |
O1—Ni1—S2 | 177.9 (2) | C41—C40—H40 | 120.1 |
O2—Ni1—S1 | 179.2 (2) | C27—C26—C25 | 120.5 (7) |
O1—Ni1—S1 | 95.23 (18) | C27—C26—H26 | 119.7 |
S2—Ni1—S1 | 84.38 (9) | C25—C26—H26 | 119.7 |
C24—S2—Ni1 | 109.5 (3) | C28—C29—C30 | 119.7 (8) |
C2—S1—Ni1 | 107.6 (3) | C28—C29—H29 | 120.1 |
C24—N4—C31 | 121.1 (6) | C30—C29—H29 | 120.1 |
C24—N4—C38 | 122.3 (6) | C22—C17—C18 | 118.5 (9) |
C31—N4—C38 | 116.6 (6) | C22—C17—C16 | 121.9 (8) |
C23—O2—Ni1 | 131.9 (5) | C18—C17—C16 | 119.6 (8) |
C23—N3—C24 | 123.0 (7) | N1—C2—N2 | 115.5 (7) |
C2—N1—C1 | 124.0 (7) | N1—C2—S1 | 127.5 (6) |
C1—O1—Ni1 | 131.5 (5) | N2—C2—S1 | 116.8 (6) |
N4—C31—C32 | 114.1 (6) | C28—C27—C26 | 120.0 (8) |
N4—C31—H31A | 108.7 | C28—C27—H27 | 120 |
C32—C31—H31A | 108.7 | C26—C27—H27 | 120 |
N4—C31—H31B | 108.7 | C11—C12—C13 | 119.4 (10) |
C32—C31—H31B | 108.7 | C11—C12—H12 | 120.3 |
H31A—C31—H31B | 107.6 | C13—C12—H12 | 120.3 |
N3—C24—N4 | 113.5 (6) | C34—C35—C36 | 120.4 (10) |
N3—C24—S2 | 127.9 (6) | C34—C35—H35 | 119.8 |
N4—C24—S2 | 118.5 (5) | C36—C35—H35 | 119.8 |
C2—N2—C9 | 122.6 (7) | C29—C30—C25 | 121.0 (8) |
C2—N2—C16 | 122.0 (7) | C29—C30—H30 | 119.5 |
C9—N2—C16 | 115.2 (6) | C25—C30—H30 | 119.5 |
C4—C3—C8 | 118.1 (8) | C32—C33—C34 | 121.2 (8) |
C4—C3—C1 | 122.5 (7) | C32—C33—H33 | 119.4 |
C8—C3—C1 | 119.4 (8) | C34—C33—H33 | 119.4 |
C26—C25—C30 | 117.8 (7) | C44—C39—C40 | 118.8 (8) |
C26—C25—C23 | 122.3 (7) | C44—C39—C38 | 118.7 (7) |
C30—C25—C23 | 119.9 (7) | C40—C39—C38 | 122.4 (7) |
C10—C15—C14 | 122.5 (9) | C20—C21—C22 | 120.3 (9) |
C10—C15—H15 | 118.7 | C20—C21—H21 | 119.8 |
C14—C15—H15 | 118.7 | C22—C21—H21 | 119.8 |
C15—C10—C11 | 117.4 (8) | C35—C36—C37 | 120.2 (8) |
C15—C10—C9 | 119.9 (8) | C35—C36—H36 | 119.9 |
C11—C10—C9 | 122.6 (7) | C37—C36—H36 | 119.9 |
N2—C9—C10 | 114.8 (6) | C3—C8—C7 | 120.6 (8) |
N2—C9—H9A | 108.6 | C3—C8—H8 | 119.7 |
C10—C9—H9A | 108.6 | C7—C8—H8 | 119.7 |
N2—C9—H9B | 108.6 | C5—C4—C3 | 121.8 (8) |
C10—C9—H9B | 108.6 | C5—C4—H4 | 119.1 |
H9A—C9—H9B | 107.5 | C3—C4—H4 | 119.1 |
N2—C16—C17 | 109.0 (7) | C21—C20—C19 | 119.1 (9) |
N2—C16—H16A | 109.9 | C21—C20—H20 | 120.4 |
C17—C16—H16A | 109.9 | C19—C20—H20 | 120.4 |
N2—C16—H16B | 109.9 | C17—C18—C19 | 119.4 (9) |
C17—C16—H16B | 109.9 | C17—C18—H18 | 120.3 |
H16A—C16—H16B | 108.3 | C19—C18—H18 | 120.3 |
C27—C28—C29 | 120.9 (7) | C42—C41—C40 | 120.6 (8) |
C27—C28—H28 | 119.5 | C42—C41—H41 | 119.7 |
C29—C28—H28 | 119.5 | C40—C41—H41 | 119.7 |
N4—C38—C39 | 112.5 (6) | C39—C44—C43 | 121.7 (8) |
N4—C38—H38A | 109.1 | C39—C44—H44 | 119.1 |
C39—C38—H38A | 109.1 | C43—C44—H44 | 119.1 |
N4—C38—H38B | 109.1 | C7—C6—C5 | 120.2 (8) |
C39—C38—H38B | 109.1 | C7—C6—H6 | 119.9 |
H38A—C38—H38B | 107.8 | C5—C6—H6 | 119.9 |
O1—C1—N1 | 129.9 (7) | C20—C19—C18 | 121.8 (9) |
O1—C1—C3 | 117.1 (7) | C20—C19—H19 | 119.1 |
N1—C1—C3 | 113.0 (8) | C18—C19—H19 | 119.1 |
O2—C23—N3 | 130.8 (7) | C14—C13—C12 | 120.2 (10) |
O2—C23—C25 | 116.6 (7) | C14—C13—H13 | 119.9 |
N3—C23—C25 | 112.5 (7) | C12—C13—H13 | 119.9 |
C32—C37—C36 | 120.1 (8) | C17—C22—C21 | 120.8 (8) |
C32—C37—H37 | 120 | C17—C22—H22 | 119.6 |
C36—C37—H37 | 120 | C21—C22—H22 | 119.6 |
C4—C5—C6 | 119.9 (8) | C6—C7—C8 | 119.4 (8) |
C4—C5—H5 | 120.1 | C6—C7—H7 | 120.3 |
C6—C5—H5 | 120.1 | C8—C7—H7 | 120.3 |
C41—C42—C43 | 119.6 (9) | C35—C34—C33 | 120.0 (9) |
C41—C42—H42 | 120.2 | C35—C34—H34 | 120 |
C43—C42—H42 | 120.2 | C33—C34—H34 | 120 |
C44—C43—C42 | 119.2 (8) | C12—C11—C10 | 121.1 (8) |
C44—C43—H43 | 120.4 | C12—C11—H11 | 119.4 |
C42—C43—H43 | 120.4 | C10—C11—H11 | 119.4 |
C37—C32—C33 | 118.2 (8) | C13—C14—C15 | 119.3 (9) |
C37—C32—C31 | 120.2 (8) | C13—C14—H14 | 120.3 |
C33—C32—C31 | 121.5 (7) | C15—C14—H14 | 120.3 |
Experimental details
Crystal data | |
Chemical formula | [Ni(C22H19N2OS)2] |
Mr | 777.61 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 294 |
a, b, c (Å) | 5.5645 (1), 19.7873 (7), 33.859 (1) |
V (Å3) | 3728.09 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.68 |
Crystal size (mm) | 0.34 × 0.05 × 0.04 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Gaussian (Coppens et al., 1965) |
Tmin, Tmax | 0.765, 0.950 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 16007, 5260, 4302 |
Rint | 0.123 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.084, 0.131, 1.17 |
No. of reflections | 5260 |
No. of parameters | 479 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.48 |
Absolute structure | Flack (1983), 1448 Friedel pairs |
Absolute structure parameter | 0.02 (3) |
Computer programs: COLLECT (Nonius, 1998), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).
Ni1—O2 | 1.837 (5) | Ni1—S2 | 2.128 (2) |
Ni1—O1 | 1.855 (5) | Ni1—S1 | 2.141 (2) |
O2—Ni1—O1 | 84.5 (2) | O2—Ni1—S1 | 179.2 (2) |
O2—Ni1—S2 | 95.94 (17) | O1—Ni1—S1 | 95.23 (18) |
O1—Ni1—S2 | 177.9 (2) | S2—Ni1—S1 | 84.38 (9) |
N-acyl-N',N'-disubstituted thioureas are well known as chelating agents. Over recent years, many transition metal complexes with N-benzoyl- and N-furoyl-N',N'-disubstituted thioureas have been reported (Jia et al., 2007). During the complex formation, the ligand is deprotonated, which results in a neutral complex with a six-membered ring chelating metal ion. In this paper, we report the crystal structure of the title compound.
In the structure, two benzoylthiourea molecules are bonded to the central NiII ion in cis positions, as shown in Fig. 1. The coordination geometry is a slightly distorted square-plane, as reflected by the angles O1—Ni1—S2 = 177.9 (2) and O2—Ni1—S1 = 179.2 (2)° (Table 1). The Ni—S and Ni—O bond lengths lie within the range of those found in the related structures (Arslan et al., 2003). The lengths of C—O, C—S and C—N bonds in the chelate ring are between characteristic single and double bond lengths (Pérez et al., 2008), which are shorter than single bond and longer than double bond. Fig. 2 shows the arrangement of the complex molecules in the unit cell.