Acta Cryst. (2007). E63, m2588 [ doi:10.1107/S1600536807045850 ]
In the title compound, [Ni(C9H10NO2S2)2], the NiII ion adopts a distorted cis-NiS2O2 square-planar geometry arising from the two S,O-bidentate ligands. The thiophene rings in each ligand are disordered, with site occupancy ratios of 0.874 (3):0.126 (3) and 0.741 (2):0.259 (2).
The preparation of the complex was been described elsewhere (Ribeiro da Silva et al., 2007). Brown plates of (I) were obtained allowing slow vaporization of a methanolic/dichloromethane (1:1) solution of the complex.
All the H atoms bonded to C atoms were refined with standard distances: 0.93 Å for aromatic and 0.98, 0.96 and 0.97 Å, for tertiary, secondary and primary aliphatic groups respectively, with Uiso(H) = 1.5Ueq(C) for methyl groups and with Uiso(H) = 1.2Ueq(C). The thiophene groups are disorded in both ligands by rotation through 180° about the pivot atoms C11 and C31.
The double and single C—C bonds of the thiophene residue were refined with the bond-length restraints 1.424 (1) and 1.362 (1) Å respectively and the S—C bond length value was assigned to be 1.712 (1) Å.
The S atoms in the disordered groups were refined isotropically with the anisotropic temperature factor of the minor component constrained to that of the respective major components by means of the EADP instruction (Sheldrick, 1997). The carbon atoms of the major (parts A) components were refined anisotropically with their anisotropic temperature factors constained to that of the pivot atoms C11 and C31, respectively, for each group by means of the EADP instruction (Sheldrick, 1997). The carbon atoms of the minor components, (parts B), were refined isotropically with U common U values defined by free variables, (Sheldrick, 1997), for each group.
Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 (Bruker, 2004) and SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
![[Figure 1]](./hb2545fig1thm.gif)
| Fig. 1. The molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level (arbitrary spheres for the H atoms). Only the major disorder components of the thiophene rings are shown. |
| [Ni(C9H10N1O2S2)2] | V = 1097.40 (8) Å3 |
| Mr = 515.31 | Z = 2 |
| Triclinic, P1 | F000 = 532 |
| Hall symbol: -P 1 | Dx = 1.559 Mg m−3 |
| a = 7.2627 (3) Å | Mo Kα radiation λ = 0.71073 Å |
| b = 10.2917 (4) Å | θ = 3.2–38.3º |
| c = 15.6218 (6) Å | µ = 1.29 mm−1 |
| α = 72.742 (2)º | T = 100 (2) K |
| β = 80.847 (3)º | Plate, brown |
| γ = 82.978 (3)º | 0.26 × 0.12 × 0.02 mm |
| Bruker SMART APEX CCD diffractometer | 3845 independent reflections |
| Radiation source: fine-focus sealed tube | 2975 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.044 |
| Detector resolution: 8.33 pixels mm-1 | θmax = 25.0º |
| T = 100(2) K | θmin = 1.4º |
| ω scans | h = −8→8 |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | k = −12→12 |
| Tmin = 0.730, Tmax = 0.975 | l = −18→18 |
| 10984 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
| wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0354P)2 + 0.6558P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.08 | (Δ/σ)max = 0.005 |
| 3845 reflections | Δρmax = 0.47 e Å−3 |
| 254 parameters | Δρmin = −0.49 e Å−3 |
| 28 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [Ni(C9H10N1O2S2)2] | γ = 82.978 (3)º |
| Mr = 515.31 | V = 1097.40 (8) Å3 |
| Triclinic, P1 | Z = 2 |
| a = 7.2627 (3) Å | Mo Kα |
| b = 10.2917 (4) Å | µ = 1.29 mm−1 |
| c = 15.6218 (6) Å | T = 100 (2) K |
| α = 72.742 (2)º | 0.26 × 0.12 × 0.02 mm |
| β = 80.847 (3)º |
| Bruker SMART APEX CCD diffractometer | 3845 independent reflections |
| Absorption correction: multi-scan (SADABS; Bruker, 2004) | 2975 reflections with I > 2σ(I) |
| Tmin = 0.730, Tmax = 0.975 | Rint = 0.044 |
| 10984 measured reflections |
| R[F2 > 2σ(F2)] = 0.041 | 28 restraints |
| wR(F2) = 0.091 | H-atom parameters constrained |
| S = 1.08 | Δρmax = 0.47 e Å−3 |
| 3845 reflections | Δρmin = −0.49 e Å−3 |
| 254 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 > 2sigma(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 | Occ. (<1) | |
| Ni1 | 0.51058 (7) | 0.10730 (4) | 0.74876 (3) | 0.01716 (14) | |
| S1 | 0.62325 (14) | 0.29040 (8) | 0.66089 (6) | 0.0231 (2) | |
| O1 | 0.5852 (3) | 0.0037 (2) | 0.66876 (15) | 0.0202 (6) | |
| O21 | 0.7603 (3) | 0.3728 (2) | 0.49805 (15) | 0.0214 (6) | |
| C2 | 0.7036 (5) | 0.2589 (3) | 0.5591 (2) | 0.0190 (8) | |
| C1 | 0.6648 (5) | 0.0293 (3) | 0.5886 (2) | 0.0182 (8) | |
| C22 | 0.8974 (5) | 0.5022 (3) | 0.3542 (2) | 0.0238 (9) | |
| H22A | 0.9868 | 0.5291 | 0.3845 | 0.029* | |
| H22B | 0.7893 | 0.5681 | 0.3509 | 0.029* | |
| C23 | 0.9853 (6) | 0.5022 (4) | 0.2594 (2) | 0.0318 (10) | |
| H23A | 1.0225 | 0.5917 | 0.2265 | 0.048* | |
| H23B | 0.8960 | 0.4773 | 0.2291 | 0.048* | |
| H23C | 1.0930 | 0.4376 | 0.2626 | 0.048* | |
| C21 | 0.8384 (5) | 0.3631 (3) | 0.4076 (2) | 0.0199 (8) | |
| H21A | 0.7452 | 0.3364 | 0.3794 | 0.024* | |
| H21B | 0.9451 | 0.2959 | 0.4110 | 0.024* | |
| C11 | 0.7005 (5) | −0.08429 (18) | 0.54975 (17) | 0.0199 (5) | |
| S11A | 0.63615 (19) | −0.24368 (11) | 0.61030 (8) | 0.0215 (3) | 0.874 (3) |
| C12A | 0.7804 (7) | −0.0818 (4) | 0.4644 (2) | 0.0199 (5) | 0.874 (3) |
| H12A | 0.8240 | −0.0036 | 0.4221 | 0.024* | 0.874 (3) |
| C13A | 0.7911 (7) | −0.2100 (3) | 0.4457 (3) | 0.0199 (5) | 0.874 (3) |
| H13A | 0.8414 | −0.2261 | 0.3909 | 0.024* | 0.874 (3) |
| C14A | 0.7169 (7) | −0.3057 (4) | 0.51981 (19) | 0.0199 (5) | 0.874 (3) |
| H14A | 0.7107 | −0.3960 | 0.5211 | 0.024* | 0.874 (3) |
| S11B | 0.8057 (14) | −0.0619 (8) | 0.4409 (3) | 0.0215 (3) | 0.126 (3) |
| C12B | 0.653 (4) | −0.2138 (12) | 0.593 (2) | 0.025 (6)* | 0.126 (3) |
| H12B | 0.5967 | −0.2367 | 0.6527 | 0.030* | 0.126 (3) |
| C13B | 0.693 (5) | −0.313 (3) | 0.5443 (17) | 0.025 (6)* | 0.126 (3) |
| H13B | 0.6715 | −0.4051 | 0.5614 | 0.030* | 0.126 (3) |
| C14B | 0.772 (4) | −0.2315 (11) | 0.465 (2) | 0.025 (6)* | 0.126 (3) |
| H14B | 0.8128 | −0.2721 | 0.4184 | 0.030* | 0.126 (3) |
| S3 | 0.40865 (14) | 0.22063 (8) | 0.84354 (6) | 0.0237 (2) | |
| O3 | 0.4300 (3) | −0.0572 (2) | 0.82358 (14) | 0.0200 (6) | |
| C31 | 0.3188 (5) | −0.2395 (2) | 0.93802 (15) | 0.0194 (6) | |
| S31A | 0.3791 (3) | −0.34726 (14) | 0.87133 (10) | 0.0214 (3) | 0.741 (2) |
| C32A | 0.2338 (8) | −0.3073 (4) | 1.0208 (2) | 0.0194 (6) | 0.741 (2) |
| H32A | 0.1934 | −0.2651 | 1.0662 | 0.023* | 0.741 (2) |
| C33A | 0.2111 (10) | −0.4474 (4) | 1.0330 (4) | 0.0194 (6) | 0.741 (2) |
| H33A | 0.1540 | −0.5067 | 1.0850 | 0.023* | 0.741 (2) |
| C34A | 0.2871 (9) | −0.4801 (4) | 0.9558 (3) | 0.0194 (6) | 0.741 (2) |
| H34A | 0.2888 | −0.5673 | 0.9495 | 0.023* | 0.741 (2) |
| S31B | 0.2082 (7) | −0.3039 (4) | 1.04503 (19) | 0.0214 (3) | 0.259 (2) |
| C32B | 0.361 (3) | −0.3334 (13) | 0.8907 (10) | 0.026 (3)* | 0.259 (2) |
| H32B | 0.4224 | −0.3112 | 0.8319 | 0.031* | 0.259 (2) |
| C33B | 0.307 (3) | −0.4676 (17) | 0.9362 (9) | 0.026 (3)* | 0.259 (2) |
| H33B | 0.3228 | −0.5442 | 0.9150 | 0.031* | 0.259 (2) |
| C34B | 0.226 (3) | −0.4553 (11) | 1.0185 (11) | 0.026 (3)* | 0.259 (2) |
| H34B | 0.1793 | −0.5315 | 1.0617 | 0.031* | 0.259 (2) |
| C41 | 0.1610 (5) | 0.0915 (3) | 1.0900 (2) | 0.0192 (8) | |
| H41A | 0.2414 | 0.0125 | 1.1172 | 0.023* | |
| H41B | 0.0475 | 0.0603 | 1.0802 | 0.023* | |
| N1 | 0.7199 (4) | 0.1486 (3) | 0.53306 (17) | 0.0187 (7) | |
| C3 | 0.3537 (5) | −0.0960 (3) | 0.9041 (2) | 0.0160 (8) | |
| C42 | 0.1151 (5) | 0.1831 (3) | 1.1506 (2) | 0.0216 (8) | |
| H42A | 0.0396 | 0.2638 | 1.1215 | 0.026* | |
| H42B | 0.2298 | 0.2121 | 1.1609 | 0.026* | |
| C4 | 0.3167 (5) | 0.1082 (3) | 0.9416 (2) | 0.0171 (8) | |
| O41 | 0.2562 (3) | 0.1712 (2) | 1.00466 (14) | 0.0190 (6) | |
| N2 | 0.2979 (4) | −0.0229 (3) | 0.96285 (17) | 0.0195 (7) | |
| C43 | 0.0080 (5) | 0.1084 (4) | 1.2414 (2) | 0.0241 (8) | |
| H43A | −0.0199 | 0.1683 | 1.2794 | 0.036* | |
| H43B | 0.0834 | 0.0291 | 1.2705 | 0.036* | |
| H43C | −0.1065 | 0.0811 | 1.2312 | 0.036* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Ni1 | 0.0219 (3) | 0.0141 (2) | 0.0156 (2) | −0.00209 (18) | −0.00078 (19) | −0.00487 (17) |
| S1 | 0.0335 (6) | 0.0172 (4) | 0.0190 (4) | −0.0064 (4) | 0.0037 (4) | −0.0076 (4) |
| O1 | 0.0266 (15) | 0.0154 (12) | 0.0189 (12) | −0.0022 (10) | 0.0002 (11) | −0.0068 (10) |
| O21 | 0.0305 (16) | 0.0152 (12) | 0.0180 (12) | −0.0039 (11) | 0.0031 (11) | −0.0062 (10) |
| C2 | 0.019 (2) | 0.0184 (18) | 0.0196 (18) | −0.0020 (15) | −0.0009 (16) | −0.0057 (15) |
| C1 | 0.014 (2) | 0.0219 (19) | 0.0187 (18) | −0.0022 (15) | −0.0032 (15) | −0.0054 (15) |
| C22 | 0.030 (2) | 0.0208 (19) | 0.0189 (18) | −0.0019 (16) | 0.0048 (17) | −0.0068 (15) |
| C23 | 0.038 (3) | 0.030 (2) | 0.023 (2) | 0.0001 (19) | 0.0012 (19) | −0.0043 (17) |
| C21 | 0.024 (2) | 0.0225 (18) | 0.0132 (17) | −0.0017 (16) | −0.0003 (15) | −0.0067 (14) |
| C11 | 0.0226 (13) | 0.0200 (11) | 0.0177 (11) | −0.0006 (9) | −0.0023 (10) | −0.0069 (10) |
| S11A | 0.0269 (7) | 0.0161 (5) | 0.0221 (7) | −0.0030 (5) | −0.0020 (5) | −0.0064 (5) |
| C12A | 0.0226 (13) | 0.0200 (11) | 0.0177 (11) | −0.0006 (9) | −0.0023 (10) | −0.0069 (10) |
| C13A | 0.0226 (13) | 0.0200 (11) | 0.0177 (11) | −0.0006 (9) | −0.0023 (10) | −0.0069 (10) |
| C14A | 0.0226 (13) | 0.0200 (11) | 0.0177 (11) | −0.0006 (9) | −0.0023 (10) | −0.0069 (10) |
| S11B | 0.0269 (7) | 0.0161 (5) | 0.0221 (7) | −0.0030 (5) | −0.0020 (5) | −0.0064 (5) |
| S3 | 0.0360 (6) | 0.0155 (4) | 0.0179 (4) | −0.0037 (4) | 0.0035 (4) | −0.0051 (4) |
| O3 | 0.0262 (15) | 0.0160 (12) | 0.0172 (12) | −0.0031 (10) | 0.0023 (11) | −0.0058 (10) |
| C31 | 0.0241 (15) | 0.0174 (11) | 0.0166 (13) | −0.0034 (9) | −0.0008 (11) | −0.0048 (9) |
| S31A | 0.0275 (8) | 0.0163 (6) | 0.0212 (7) | −0.0031 (5) | −0.0008 (6) | −0.0070 (5) |
| C32A | 0.0241 (15) | 0.0174 (11) | 0.0166 (13) | −0.0034 (9) | −0.0008 (11) | −0.0048 (9) |
| C33A | 0.0241 (15) | 0.0174 (11) | 0.0166 (13) | −0.0034 (9) | −0.0008 (11) | −0.0048 (9) |
| C34A | 0.0241 (15) | 0.0174 (11) | 0.0166 (13) | −0.0034 (9) | −0.0008 (11) | −0.0048 (9) |
| S31B | 0.0275 (8) | 0.0163 (6) | 0.0212 (7) | −0.0031 (5) | −0.0008 (6) | −0.0070 (5) |
| C41 | 0.021 (2) | 0.0180 (17) | 0.0182 (18) | −0.0049 (15) | 0.0020 (16) | −0.0048 (14) |
| N1 | 0.0218 (18) | 0.0182 (15) | 0.0168 (15) | −0.0011 (13) | −0.0005 (13) | −0.0073 (12) |
| C3 | 0.0109 (19) | 0.0192 (17) | 0.0183 (18) | 0.0004 (14) | −0.0053 (15) | −0.0049 (14) |
| C42 | 0.023 (2) | 0.0211 (18) | 0.0221 (19) | −0.0031 (15) | −0.0035 (16) | −0.0067 (15) |
| C4 | 0.016 (2) | 0.0193 (18) | 0.0180 (17) | 0.0000 (14) | −0.0014 (15) | −0.0088 (14) |
| O41 | 0.0252 (15) | 0.0151 (12) | 0.0165 (12) | −0.0045 (10) | 0.0020 (11) | −0.0054 (10) |
| N2 | 0.0259 (19) | 0.0161 (15) | 0.0175 (15) | −0.0018 (13) | −0.0001 (13) | −0.0077 (12) |
| C43 | 0.024 (2) | 0.028 (2) | 0.0210 (18) | −0.0015 (16) | −0.0015 (16) | −0.0092 (15) |
| Ni1—O1 | 1.851 (2) | C13B—H13B | 0.9300 |
| Ni1—O3 | 1.851 (2) | C14B—H14B | 0.9300 |
| Ni1—S3 | 2.1368 (10) | S3—C4 | 1.715 (3) |
| Ni1—S1 | 2.1424 (9) | O3—C3 | 1.259 (4) |
| S1—C2 | 1.715 (3) | C31—C32B | 1.3619 (10) |
| O1—C1 | 1.258 (4) | C31—C32A | 1.3623 (10) |
| O21—C2 | 1.335 (4) | C31—C3 | 1.453 (4) |
| O21—C21 | 1.464 (4) | C31—S31B | 1.7104 (10) |
| C2—N1 | 1.302 (4) | C31—S31A | 1.7117 (10) |
| C1—N1 | 1.341 (4) | S31A—C34A | 1.7113 (10) |
| C1—C11 | 1.449 (4) | C32A—C33A | 1.4237 (10) |
| C22—C21 | 1.502 (4) | C32A—H32A | 0.9300 |
| C22—C23 | 1.516 (5) | C33A—C34A | 1.3618 (10) |
| C22—H22A | 0.9700 | C33A—H33A | 0.9300 |
| C22—H22B | 0.9700 | C34A—H34A | 0.9300 |
| C23—H23A | 0.9600 | S31B—C34B | 1.7120 (10) |
| C23—H23B | 0.9600 | C32B—C33B | 1.4239 (10) |
| C23—H23C | 0.9600 | C32B—H32B | 0.9300 |
| C21—H21A | 0.9700 | C33B—C34B | 1.3618 (10) |
| C21—H21B | 0.9700 | C33B—H33B | 0.9300 |
| C11—C12A | 1.3617 (10) | C34B—H34B | 0.9300 |
| C11—C12B | 1.3619 (10) | C41—O41 | 1.458 (4) |
| C11—S11B | 1.7110 (10) | C41—C42 | 1.498 (5) |
| C11—S11A | 1.7119 (10) | C41—H41A | 0.9700 |
| S11A—C14A | 1.7115 (10) | C41—H41B | 0.9700 |
| C12A—C13A | 1.4236 (10) | C3—N2 | 1.337 (4) |
| C12A—H12A | 0.9300 | C42—C43 | 1.536 (4) |
| C13A—C14A | 1.3618 (10) | C42—H42A | 0.9700 |
| C13A—H13A | 0.9300 | C42—H42B | 0.9700 |
| C14A—H14A | 0.9300 | C4—N2 | 1.310 (4) |
| S11B—C14B | 1.7121 (10) | C4—O41 | 1.325 (4) |
| C12B—C13B | 1.4239 (10) | C43—H43A | 0.9600 |
| C12B—H12B | 0.9300 | C43—H43B | 0.9600 |
| C13B—C14B | 1.3620 (10) | C43—H43C | 0.9600 |
| O1—Ni1—O3 | 82.18 (9) | C13B—C14B—H14B | 116.6 |
| O1—Ni1—S3 | 176.43 (8) | S11B—C14B—H14B | 116.6 |
| O3—Ni1—S3 | 95.16 (7) | C4—S3—Ni1 | 107.56 (12) |
| O1—Ni1—S1 | 95.46 (7) | C3—O3—Ni1 | 134.2 (2) |
| O3—Ni1—S1 | 175.91 (8) | C32B—C31—C32A | 105.8 (8) |
| S3—Ni1—S1 | 87.33 (4) | C32B—C31—C3 | 125.9 (7) |
| C2—S1—Ni1 | 106.78 (12) | C32A—C31—C3 | 128.3 (2) |
| C1—O1—Ni1 | 133.9 (2) | C32B—C31—S31B | 113.5 (7) |
| C2—O21—C21 | 117.4 (2) | C3—C31—S31B | 120.5 (2) |
| N1—C2—O21 | 117.4 (3) | C32A—C31—S31A | 110.4 (2) |
| N1—C2—S1 | 132.4 (3) | C3—C31—S31A | 121.32 (19) |
| O21—C2—S1 | 110.2 (2) | S31B—C31—S31A | 118.11 (19) |
| O1—C1—N1 | 128.8 (3) | C34A—S31A—C31 | 91.1 (2) |
| O1—C1—C11 | 116.3 (3) | C31—C32A—C33A | 115.4 (4) |
| N1—C1—C11 | 114.9 (3) | C31—C32A—H32A | 122.3 |
| C21—C22—C23 | 110.7 (3) | C33A—C32A—H32A | 122.3 |
| C21—C22—H22A | 109.5 | C34A—C33A—C32A | 108.6 (5) |
| C23—C22—H22A | 109.5 | C34A—C33A—H33A | 125.7 |
| C21—C22—H22B | 109.5 | C32A—C33A—H33A | 125.7 |
| C23—C22—H22B | 109.5 | C33A—C34A—S31A | 114.4 (4) |
| H22A—C22—H22B | 108.1 | C33A—C34A—H34A | 122.8 |
| C22—C23—H23A | 109.5 | S31A—C34A—H34A | 122.8 |
| C22—C23—H23B | 109.5 | C31—S31B—C34B | 85.6 (6) |
| H23A—C23—H23B | 109.5 | C31—C32B—C33B | 116.5 (13) |
| C22—C23—H23C | 109.5 | C31—C32B—H32B | 121.8 |
| H23A—C23—H23C | 109.5 | C33B—C32B—H32B | 121.8 |
| H23B—C23—H23C | 109.5 | C34B—C33B—C32B | 102.4 (16) |
| O21—C21—C22 | 106.6 (3) | C34B—C33B—H33B | 128.8 |
| O21—C21—H21A | 110.4 | C32B—C33B—H33B | 128.8 |
| C22—C21—H21A | 110.4 | C33B—C34B—S31B | 122.1 (14) |
| O21—C21—H21B | 110.4 | C33B—C34B—H34B | 119.0 |
| C22—C21—H21B | 110.4 | S31B—C34B—H34B | 119.0 |
| H21A—C21—H21B | 108.6 | O41—C41—C42 | 107.0 (3) |
| C12A—C11—C12B | 107.6 (15) | O41—C41—H41A | 110.3 |
| C12A—C11—C1 | 127.3 (2) | C42—C41—H41A | 110.3 |
| C12B—C11—C1 | 125.0 (15) | O41—C41—H41B | 110.3 |
| C12B—C11—S11B | 114.3 (15) | C42—C41—H41B | 110.3 |
| C1—C11—S11B | 120.7 (3) | H41A—C41—H41B | 108.6 |
| C12A—C11—S11A | 111.4 (2) | C2—N1—C1 | 122.2 (3) |
| C1—C11—S11A | 121.3 (2) | O3—C3—N2 | 129.0 (3) |
| S11B—C11—S11A | 118.0 (3) | O3—C3—C31 | 115.8 (3) |
| C14A—S11A—C11 | 91.11 (18) | N2—C3—C31 | 115.2 (3) |
| C11—C12A—C13A | 113.8 (3) | C41—C42—C43 | 110.5 (3) |
| C11—C12A—H12A | 123.1 | C41—C42—H42A | 109.5 |
| C13A—C12A—H12A | 123.1 | C43—C42—H42A | 109.5 |
| C14A—C13A—C12A | 110.2 (4) | C41—C42—H42B | 109.5 |
| C14A—C13A—H13A | 124.9 | C43—C42—H42B | 109.5 |
| C12A—C13A—H13A | 124.9 | H42A—C42—H42B | 108.1 |
| C13A—C14A—S11A | 113.5 (3) | N2—C4—O41 | 117.5 (3) |
| C13A—C14A—H14A | 123.2 | N2—C4—S3 | 131.7 (3) |
| S11A—C14A—H14A | 123.2 | O41—C4—S3 | 110.7 (2) |
| C11—S11B—C14B | 82.7 (11) | C4—O41—C41 | 117.4 (2) |
| C11—C12B—C13B | 118 (3) | C4—N2—C3 | 122.3 (3) |
| C11—C12B—H12B | 121.0 | C42—C43—H43A | 109.5 |
| C13B—C12B—H12B | 121.0 | C42—C43—H43B | 109.5 |
| C14B—C13B—C12B | 98 (3) | H43A—C43—H43B | 109.5 |
| C14B—C13B—H13B | 131.0 | C42—C43—H43C | 109.5 |
| C12B—C13B—H13B | 131.0 | H43A—C43—H43C | 109.5 |
| C13B—C14B—S11B | 127 (2) | H43B—C43—H43C | 109.5 |
| Ni1—O1 | 1.851 (2) | Ni1—S3 | 2.1368 (10) |
| Ni1—O3 | 1.851 (2) | Ni1—S1 | 2.1424 (9) |
BS thanks the Fundação para a Ciência e Técnologia, Lisboa, Portugal, and the European Social Fund (ESF) under the 3rd Community Support Framework (CSF) for the award of a postdoctoral scholarship (grant No. PRAXIS XXI/BPD 35131/2000). The authors acknowledge financial support from the Fundação para a Ciência e Técnologia (grant No. POCI/QUI/61873/2004).
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
Binzet, G., Flörke, U., Külcü, N. & Arslan, H. (2003). Acta Cryst. E59, m705–m706.
Bruker (2004). APEX (Version 5.62) [Should this be APEX2 as above? If so, please give correct version number], SAINT (Version 6.02), SHELXTL (Version 6.10) and SADABS (Version 2.03). Bruker AXS Inc., Madison, Wisconsin, USA.
Emen, F. M., Flörke, U., Külcü, N. & Arslan, H. (2003). Acta Cryst. E59, m582–m583.
Gomes, L. R., Santos, L. M. N. B. F., Schröder, B., Wagner, C. & Low, J. N. (2007). Acta Cryst. E63, m953–m955.
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA.
Ribeiro da Silva, M. A. V., Santos, L. M. N. B. F. & Schröder, B. (2007). J. Chem. Thermodyn. 39, 684–688.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13.
The title compound, (I), was synthesized in the course of our studies of the thermochemical properties of thiocarbamate derivates in order to elucidate the binding process in complexes with transition metal ions (Ribeiro da Silva et al., 2007).
The ligand (N-2thienylcarbonylthiocarbamic-O-propylester) combines with the nickel(II) ion to from a tetra co-ordinated complex with an S2O2 co-ordination sphere in a cis configuration (Fig. 1, Table 1). The complex shows a slightly distortion to square planar geometry, where the maximum deviation of the atoms from the best plane formed by the five central atoms are: 0.043 (1), 0.053 (1), 0.043 (1), 0.053 (1) and 0.009 (1) Å, for S1, O1, S3 O3 and Ni1, respectively.
Otherwise, the bond lengths involving the ligands are within the range reported for similar complexes, derived from thioureas (Gomes et al., 2007; Emen et al., 2003); Binzet et al., 2003).