Acta Cryst. (2009). E65, m1450 [ doi:10.1107/S160053680904361X ]
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O)bis(mercaptoacetato-2O,S)tin(IV)In the title compound, [Sn(C2H2O2S)2(C2H6OS)2], the mercaptoacetato ligands chelate to SnIV through S and one O atoms. The metal centre is also coordinated by two dimethyl sulfoxide (DMSO) ligands through the O atom, leading to an overall distorted octahedral coordination environment for the SnIV atom. The molecular adduct lies on a twofold rotation axis.
All chemicals were obtained from commercial sources and were used as received. The title compound was handily synthesized by a solution reaction from mercapto acetic acid. HSCH2COOH (56 mg, 0.6 mmol) and NaOH (50 mg, 1.2 mmol) was dissolved in 10 ml of water. To this solution was added a 5 ml aqueous solution of SnCl4.5H2O (106 mg, 0.3 mmol) at room temperature. Amount of white precipitates were gradually formed and colected by filtrating and washing with water. Then they were dissolved in 5 ml DMSO and the filtration was slowly evaperated at room temperature. After several days, a great deal of colorless crystals were obtained, yield about 113 mg (83% on tin).
The structure was solved using direct methods and refined by full-matrix least-squares techniques. All non-hydrogen atoms were assigned anisotropic displacement parameters in the refinement. All hydrogen atoms were added at calculated positions and refined using a riding model. The structure was refined on F2 using SHELXTL97 software package(Sheldrick et al., 2008) without any unusual events.
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./ng2673fig1thm.gif)
| Fig. 1. Structure and labeling of the title compound, with displacement ellipsoids drawn at the 30% probability level and H atoms shown as small spheres of arbitrary radii. |
![[Figure 2]](./ng2673fig2thm.gif)
| Fig. 2. The packing diagram viewed along the b-direction. |
| [Sn(C2H2O2S)2(C2H6OS)2] | F(000) = 904 |
| Mr = 455.14 | Dx = 1.923 Mg m−3 |
| Monoclinic, C2/c | Mo Kα radiation, λ = 0.71075 Å |
| Hall symbol: -C 2yc | Cell parameters from 2229 reflections |
| a = 13.3460 (17) Å | θ = 3.1–27.5° |
| b = 8.2706 (7) Å | µ = 2.17 mm−1 |
| c = 14.9053 (18) Å | T = 130 K |
| β = 107.124 (5)° | Prism, white |
| V = 1572.3 (3) Å3 | 0.20 × 0.15 × 0.15 mm |
| Z = 4 |
| Rigaku R-AXIS RAPID diffractometer | 1800 independent reflections |
| Radiation source: fine-focus sealed tube | 1718 reflections with I > 2σ(I) |
| graphite | Rint = 0.021 |
| Detector resolution: 14.6306 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
| CCD_Profile_fitting scans | h = −11→17 |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −10→10 |
| Tmin = 0.671, Tmax = 0.737 | l = −19→19 |
| 5801 measured reflections |
| 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)] = 0.020 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.047 | H-atom parameters constrained |
| S = 1.10 | w = 1/[σ2(Fo2) + (0.0207P)2 + 2.5592P] where P = (Fo2 + 2Fc2)/3 |
| 1800 reflections | (Δ/σ)max = 0.001 |
| 87 parameters | Δρmax = 0.75 e Å−3 |
| 0 restraints | Δρmin = −0.43 e Å−3 |
| [Sn(C2H2O2S)2(C2H6OS)2] | V = 1572.3 (3) Å3 |
| Mr = 455.14 | Z = 4 |
| Monoclinic, C2/c | Mo Kα radiation |
| a = 13.3460 (17) Å | µ = 2.17 mm−1 |
| b = 8.2706 (7) Å | T = 130 K |
| c = 14.9053 (18) Å | 0.20 × 0.15 × 0.15 mm |
| β = 107.124 (5)° |
| Rigaku R-AXIS RAPID diffractometer | 1800 independent reflections |
| Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1718 reflections with I > 2σ(I) |
| Tmin = 0.671, Tmax = 0.737 | Rint = 0.021 |
| 5801 measured reflections | θmax = 27.5° |
| R[F2 > 2σ(F2)] = 0.020 | H-atom parameters constrained |
| wR(F2) = 0.047 | Δρmax = 0.75 e Å−3 |
| S = 1.10 | Δρmin = −0.43 e Å−3 |
| 1800 reflections | Absolute structure: ? |
| 87 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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 | ||
| Sn1 | 0.0000 | 0.20692 (2) | 0.7500 | 0.01316 (7) | |
| S1 | −0.04306 (4) | 0.02254 (7) | 0.61815 (4) | 0.02162 (12) | |
| S2 | 0.22228 (4) | 0.12036 (6) | 0.71261 (3) | 0.01444 (11) | |
| O1 | −0.04086 (11) | 0.39054 (17) | 0.65158 (10) | 0.0164 (3) | |
| O2 | −0.13288 (14) | 0.4586 (2) | 0.50766 (10) | 0.0285 (4) | |
| O3 | 0.16014 (11) | 0.24764 (18) | 0.75112 (10) | 0.0179 (3) | |
| C1 | −0.09221 (16) | 0.3555 (3) | 0.56564 (14) | 0.0194 (4) | |
| C2 | −0.1050 (2) | 0.1784 (3) | 0.53429 (16) | 0.0296 (5) | |
| H2B | −0.0781 | 0.1677 | 0.4794 | 0.036* | |
| H2A | −0.1811 | 0.1547 | 0.5122 | 0.036* | |
| C3 | 0.22763 (19) | 0.2033 (3) | 0.60389 (15) | 0.0239 (5) | |
| H3A | 0.1588 | 0.1928 | 0.5571 | 0.036* | |
| H3B | 0.2801 | 0.1449 | 0.5823 | 0.036* | |
| H3C | 0.2469 | 0.3178 | 0.6124 | 0.036* | |
| C4 | 0.35322 (16) | 0.1546 (3) | 0.78190 (16) | 0.0215 (4) | |
| H4A | 0.3626 | 0.1143 | 0.8457 | 0.032* | |
| H4B | 0.3682 | 0.2708 | 0.7842 | 0.032* | |
| H4C | 0.4013 | 0.0978 | 0.7542 | 0.032* |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| Sn1 | 0.00996 (10) | 0.01364 (11) | 0.01662 (10) | 0.000 | 0.00506 (7) | 0.000 |
| S1 | 0.0191 (3) | 0.0178 (3) | 0.0260 (3) | 0.0000 (2) | 0.0035 (2) | −0.0068 (2) |
| S2 | 0.0111 (2) | 0.0132 (2) | 0.0194 (2) | 0.00096 (18) | 0.00510 (19) | −0.00037 (17) |
| O1 | 0.0143 (7) | 0.0163 (7) | 0.0177 (6) | −0.0018 (6) | 0.0033 (6) | 0.0011 (5) |
| O2 | 0.0319 (9) | 0.0303 (9) | 0.0192 (7) | 0.0098 (7) | 0.0013 (7) | 0.0025 (7) |
| O3 | 0.0106 (7) | 0.0193 (7) | 0.0259 (7) | −0.0017 (6) | 0.0086 (6) | −0.0053 (6) |
| C1 | 0.0132 (10) | 0.0253 (11) | 0.0206 (10) | 0.0041 (8) | 0.0063 (8) | −0.0018 (8) |
| C2 | 0.0264 (12) | 0.0304 (13) | 0.0231 (11) | 0.0113 (10) | −0.0065 (10) | −0.0076 (9) |
| C3 | 0.0250 (12) | 0.0303 (12) | 0.0180 (9) | 0.0026 (9) | 0.0088 (9) | 0.0008 (9) |
| C4 | 0.0117 (10) | 0.0217 (10) | 0.0280 (11) | 0.0037 (8) | 0.0013 (9) | −0.0023 (9) |
| Sn1—O1i | 2.0699 (14) | O2—C1 | 1.222 (3) |
| Sn1—O1 | 2.0699 (14) | C1—C2 | 1.531 (3) |
| Sn1—O3 | 2.1587 (14) | C2—H2B | 0.9900 |
| Sn1—O3i | 2.1587 (14) | C2—H2A | 0.9900 |
| Sn1—S1 | 2.4193 (6) | C3—H3A | 0.9800 |
| Sn1—S1i | 2.4193 (6) | C3—H3B | 0.9800 |
| S1—C2 | 1.817 (2) | C3—H3C | 0.9800 |
| S2—O3 | 1.5511 (15) | C4—H4A | 0.9800 |
| S2—C4 | 1.771 (2) | C4—H4B | 0.9800 |
| S2—C3 | 1.780 (2) | C4—H4C | 0.9800 |
| O1—C1 | 1.295 (2) | ||
| O1i—Sn1—O1 | 85.61 (8) | O2—C1—O1 | 122.6 (2) |
| O1i—Sn1—O3 | 80.01 (6) | O2—C1—C2 | 117.72 (19) |
| O1—Sn1—O3 | 86.83 (6) | O1—C1—C2 | 119.67 (19) |
| O1i—Sn1—O3i | 86.83 (6) | C1—C2—S1 | 118.77 (16) |
| O1—Sn1—O3i | 80.01 (6) | C1—C2—H2B | 107.6 |
| O3—Sn1—O3i | 162.05 (8) | S1—C2—H2B | 107.6 |
| O1i—Sn1—S1 | 171.18 (4) | C1—C2—H2A | 107.6 |
| O1—Sn1—S1 | 86.38 (4) | S1—C2—H2A | 107.6 |
| O3—Sn1—S1 | 95.88 (4) | H2B—C2—H2A | 107.1 |
| O3i—Sn1—S1 | 95.41 (4) | S2—C3—H3A | 109.5 |
| O1i—Sn1—S1i | 86.38 (4) | S2—C3—H3B | 109.5 |
| O1—Sn1—S1i | 171.18 (4) | H3A—C3—H3B | 109.5 |
| O3—Sn1—S1i | 95.41 (4) | S2—C3—H3C | 109.5 |
| O3i—Sn1—S1i | 95.88 (4) | H3A—C3—H3C | 109.5 |
| S1—Sn1—S1i | 101.85 (3) | H3B—C3—H3C | 109.5 |
| C2—S1—Sn1 | 93.60 (8) | S2—C4—H4A | 109.5 |
| O3—S2—C4 | 102.64 (9) | S2—C4—H4B | 109.5 |
| O3—S2—C3 | 104.15 (10) | H4A—C4—H4B | 109.5 |
| C4—S2—C3 | 99.90 (11) | S2—C4—H4C | 109.5 |
| C1—O1—Sn1 | 119.26 (14) | H4A—C4—H4C | 109.5 |
| S2—O3—Sn1 | 121.82 (8) | H4B—C4—H4C | 109.5 |
| O1i—Sn1—S1—C2 | −36.3 (3) | C3—S2—O3—Sn1 | 106.14 (12) |
| O1—Sn1—S1—C2 | −11.53 (10) | O1i—Sn1—O3—S2 | 161.54 (11) |
| O3—Sn1—S1—C2 | −97.96 (10) | O1—Sn1—O3—S2 | −112.37 (10) |
| O3i—Sn1—S1—C2 | 68.06 (10) | O3i—Sn1—O3—S2 | −155.05 (10) |
| S1i—Sn1—S1—C2 | 165.24 (9) | S1—Sn1—O3—S2 | −26.35 (10) |
| O1i—Sn1—O1—C1 | −169.37 (17) | S1i—Sn1—O3—S2 | 76.19 (10) |
| O3—Sn1—O1—C1 | 110.43 (15) | Sn1—O1—C1—O2 | 168.26 (17) |
| O3i—Sn1—O1—C1 | −81.82 (15) | Sn1—O1—C1—C2 | −10.7 (3) |
| S1—Sn1—O1—C1 | 14.32 (14) | O2—C1—C2—S1 | 178.66 (18) |
| S1i—Sn1—O1—C1 | −144.6 (2) | O1—C1—C2—S1 | −2.3 (3) |
| C4—S2—O3—Sn1 | −150.07 (11) | Sn1—S1—C2—C1 | 10.8 (2) |
| Symmetry codes: (i) −x, y, −z+3/2. |
The author is grateful for financial support from the Scientific Research Fund of Zhejiang Provincial Education Department (grant No. 20070358), the Analysis and Testing Foundation of Zhejiang Province (grant Nos. 2008 F70034 and 2008 F70053) and the Young Scientists Fund of the Key Laboratory of Advanced Textile Materials and Manufacturing Technology of the Ministry of Education (grant No. 2007QN01).
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan.
Holmes, R. R., Shafieezad, S., Holmes, J. M. & Day, R. O. (1988). Inorg. Chem. 27, 1232–1237.
Ng, S. W., Kumar Das, V. G., Yap, G. & Rheingold, A. L. (1996). Acta Cryst. C52, 1369–1371.
Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2004). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.
Smith, P. J. (1998). Chemistry of Tin. CITY OF PUBLICATION: Blackie Academic & Professional.
Song, X. Q., Xie, Q. L. & Fang, X. N. (1998). Chin. Chem. Lett. 9, 977–978.
Song, X. Q., Zhong, G. Y., Xie, Q. L. & Eng, G. (2005). Inorg. Chem. Commun. 8, 725–728.
Wu, L.-M., Chen, L., Dai, J.-C., Lin, P., Du, W.-X. & Wu, X.-T. (2000). Acta Cryst. C56, e382.
Zhang, R. F., Zhang, Q. F., Shi, Y. & Ma, C. L. (2006). J. Organomet. Chem. 691, 1668–1171.
Zhong, G. Y., Liu, Q. F., Song, X. Q., Eng, G. & Xie, Q. L. (2005a). J. Organomet. Chem. 690, 3405–3409.
Zhong, G. Y., Song, H. B., Sun, L. J. & Xie, Q. L. (2005b). Appl. Organomet. Chem. 19, 388–389.
Zhong, G. Y., Song, H. B., Xie, Q. L. & Sun, L. J. (2004a). Chem. J. Chin. Univ. 25, 2287–2289.
Zhong, G. Y., Song, H. B., Xie, Q. L. & Sun, L. J. (2004b). Chem. Res. Chin. Univ. 20, 274–276.
Compared with organotin compounds, inorganic compounds of tin are also important in industry applications, for example, electroplating, ceramic glazes and pigments,heterogeneous catalysts, gas sensors, and so on. (Smith et al., 1998) Perhaps the most important recent development in tin (iv) chemistry has been the increase in studies of the solid state properties of tin (iv) compounds. Sn(SCH2CH2S)2 could act as a typical Lewis acid and reveal to be a electron acceptor. And many structures have been reported to exhibit the reaction of Sn(SCH2CH2S)2 and ligands. (Wu et al., 2000; Holmes et al., 1988) Here, the S-contained chelated ligand is mercapto acetic acid but not 1,2-ethanedithiol ligand, and the solvent DMSO act as the second ligand.
The title compound, Sn(C2H2O2S)2(DMSO)2, is a mononuclear structure and crystallizes in monoclinic form in the space group C2/c. As shown in Figure 1, the asymmetric unit is composed of half tin atom, one mercaptoacetato and one DMSO ligand. According to a C2 symmetry axis pass the tin (iv) site, a mononuclear structure is present. In which, two mercaptoacetato ligands coordinates to SnIV through S and one O atoms. The metal centre is also coordinated by two dimethyl sulfoxide ligands through O atom, froming a SnO4S2 distorted octahedronal coordianted sphere. Around the metal centre, two mercaptoacetato ligands adopt cis chelated mode to form a SnO2S2 distorted equatorial plan. And other two DMSO ligands join on it from two polars of the coordinated sphere, also with cis mode around the metal centre.