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Volume 68 
Part 11 
Page m1337  
November 2012  

Received 15 July 2012
Accepted 26 September 2012
Online 6 October 2012

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.004 Å
R = 0.030
wR = 0.066
Data-to-parameter ratio = 17.8
Details
Open access

[mu]2-Oxalato-bis[triphenyl(thiourea-[kappa]S)tin(IV)]

aLaboratoire de Chimie Minerale et Analytique (LACHIMIA), Departement de Chimie, Faculte des Sciences et Techniques, Universite Cheikh, Anta Diop Dakar Senegal, and bDepartment of Chemistry, University of Bath, Bath BA2 7AY, England
Correspondence e-mail: yayasow81@yahoo.fr

The asymmetric unit of the binuclear title compound, [Sn2(C2O4)(C6H5)6(CH4N2S)2], consists of one half of the organotin(IV) molecule. The remainder is generated by a twofold rotation axis passing through the mid-point of the oxalate C-C bond. The SnIV atom exhibits a distorted trigonal-bipyramidal coordination environment with the phenyl groups in equatorial positions and the thiourea and the monodentately bridging oxalate anion in axial positions. The molecules are linked through N-H...O hydrogen bonds involving the amino group of the thiourea ligand and the uncoordinating oxalate O atoms, forming layers parallel to (001). Weak C-H...O interactions are also present.

Related literature

For background to organotin(IV) chemistry, see: Evans & Karpel (1985[Evans, C. J. & Karpel, S. (1985). Organotin Compounds in Modern Technology, J. Organomet. Chem. Library, Vol. 16. Amsterdam: Elsevier.]); Gielen et al. (1995[Gielen, M., Bouhdid, A., Kayser, S., Biesemans, M., De Vos, D., Mahieu, B. & Willem, R. (1995). Appl. Organomet. Chem. 9, 251-257.]). For triphenyltin(IV)-containing compounds and their biological activity, see: Kamruddin et al. (1996[Kamruddin, S. K., Chattopadhyaya, T. K., Roy, A. & Tiekink, E. R. T. (1996). Appl. Organomet. Chem. 10, 513-521.]). For related compounds, see: Diallo et al. (2009[Diallo, W., Okio, K. Y. A., Diop, C. A. K., Diop, L., Diop, L. A. & Russo, U. (2009). Main Group. Met. Chem. 32, 93-100.]); Diasse-Sarr et al. (1997[Diasse-Sarr, A., Diop, L., Mahon, M. & Molloy, K. C. (1997). Main Group Met. Chem. 20, 223-229.]); Diop et al. (1997[Diop, C. A. K., Lahlou, M., Diop, L., Mahieu, B. & Russo, U. (1997). Main Group Met. Chem. 20, 681-686.], 1999[Diop, C. A. K., Diop, L. & Russo, U. (1999). Main Group. Met. Chem. 22, 217-220.], 2003[Diop, L., Mahieu, B., Mahon, M. F., Molloy, K. C. & Okio, K. Y. A. (2003). Appl. Organomet. Chem. 17, 881-882.]); Tiekink (1992[Tiekink, E. R. T. (1992). Main Group Met.Chem. 15, 161-186.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn2(C2O4)(C6H5)6(CH4N2S)2]

  • Mr = 940.24

  • Monoclinic, C 2/c

  • a = 12.9161 (2) Å

  • b = 13.9870 (2) Å

  • c = 21.8215 (3) Å

  • [beta] = 99.238 (1)°

  • V = 3891.09 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.44 mm-1

  • T = 150 K

  • 0.30 × 0.30 × 0.20 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (SORTAV; Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.659, Tmax = 0.747

  • 31403 measured reflections

  • 4472 independent reflections

  • 3665 reflections with I > 2[sigma](I)

  • Rint = 0.057

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.066

  • S = 1.09

  • 4472 reflections

  • 251 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 1.34 e Å-3

  • [Delta][rho]min = -1.11 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O2i 0.81 (4) 2.06 (4) 2.824 (3) 157 (4)
N2-H2A...O2ii 0.86 (4) 2.14 (4) 2.970 (3) 164 (3)
C6-H6...O1 0.95 2.44 2.957 (3) 114
C18-H18...O2 0.95 2.39 3.234 (3) 147
Symmetry codes: (i) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x+{\script{1\over 2}}, y+{\script{1\over 2}}, z].

Data collection: COLLECT (Nonius, 1999[Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C.W.Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: WinGX (Farrugia,1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2662 ).


References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.  [ISI] [CrossRef] [ChemPort] [details]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [details]
Diallo, W., Okio, K. Y. A., Diop, C. A. K., Diop, L., Diop, L. A. & Russo, U. (2009). Main Group. Met. Chem. 32, 93-100.  [ChemPort]
Diasse-Sarr, A., Diop, L., Mahon, M. & Molloy, K. C. (1997). Main Group Met. Chem. 20, 223-229.  [ChemPort]
Diop, C. A. K., Diop, L. & Russo, U. (1999). Main Group. Met. Chem. 22, 217-220.  [ChemPort]
Diop, C. A. K., Lahlou, M., Diop, L., Mahieu, B. & Russo, U. (1997). Main Group Met. Chem. 20, 681-686.  [ChemPort]
Diop, L., Mahieu, B., Mahon, M. F., Molloy, K. C. & Okio, K. Y. A. (2003). Appl. Organomet. Chem. 17, 881-882.  [ISI] [CSD] [CrossRef] [ChemPort]
Evans, C. J. & Karpel, S. (1985). Organotin Compounds in Modern Technology, J. Organomet. Chem. Library, Vol. 16. Amsterdam: Elsevier.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.  [CrossRef] [ChemPort] [details]
Gielen, M., Bouhdid, A., Kayser, S., Biesemans, M., De Vos, D., Mahieu, B. & Willem, R. (1995). Appl. Organomet. Chem. 9, 251-257.  [CrossRef] [ChemPort] [ISI]
Kamruddin, S. K., Chattopadhyaya, T. K., Roy, A. & Tiekink, E. R. T. (1996). Appl. Organomet. Chem. 10, 513-521.  [CrossRef] [ChemPort]
Nonius (1999). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C.W.Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tiekink, E. R. T. (1992). Main Group Met.Chem. 15, 161-186.  [ChemPort]


Acta Cryst (2012). E68, m1337  [ doi:10.1107/S1600536812040706 ]

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