(1,5-Diphenyl­thio­carbazonato-κS)trimethyl­tin(IV)

Von Eschwege, K.G.; Swarts, J.C.; Aquino, M.A.S.; Cameron, T.S.

doi:10.1107/S1600536812047216

Volume 68
Part 12
Page m1518
December 2012

Received 6 November 2012
Accepted 16 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 223 K
Mean (C-C) = 0.003 Å
R = 0.027
wR = 0.027
Data-to-parameter ratio = 15.0
Details

(1,5-Diphenylthiocarbazonato-S)trimethyltin(IV)

Karel G. Von Eschwege,^a ^* Jannie C. Swarts,^a Manuel A. S. Aquino ^b and T. Stanley Cameron ^c

^aDepartment of Chemistry, University of the Free State, PO Box 339, Bloemfontein, 9300, South Africa,^bDepartment of Chemistry, St Francis Xavier University, PO Box 5000, Antigonish, Nova Scotia B2G 2W5, Canada, and ^cDepartment of Chemistry, Dalhousie University, Halifax, Nova Scotia, B3H 4J3, Canada
Correspondence e-mail: veschwkg@ufs.ac.za

In the title compound, [Sn(C₁₃H₁₁N₄S)(CH₃)₃], the Sn^IV atom is coordinated by an S atom from the 1,5-diphenylthiocarbazonato (L) ligand [Sn-S 2.4710 (6) Å] and by three methyl groups [Sn-C 2.123 (3)-2.130 (2) Å] in a distorted tetrahedral geometry. The aromatic rings of the L ligand form a dihedral angle of 2.1 (1)°.

Related literature

For general background to dithizone and dithizonato metal complexes, see: Irving (1977). For the synthesis of dithizone, see: Pelkis et al. (1957). For structural aspects of dithizone and its oxidation products and observed solvatochromism and concentratochromism, see: Von Eschwege et al. (2011a). For related ligand and complex structures, see: Harrowfield et al. (1983); Kong & Wong (1999); Herbstein & Schwotzer (1984); Fernandes et al. (2002); Von Eschwege et al. (2008); Laing et al. (1971). For electrochemical studies of dithizone and its Hg complex, see: Von Eschwege & Swarts (2010); Von Eschwege et al. (2011b). For femto second laser spectroscopy studies on a photochromic dithizonatomercury complex, see: Schwoerer et al. (2011). For the weighting scheme, see: Carruthers & Watkin (1979).

Experimental

Crystal data

[Sn(C₁₃H₁₁N₄S)(CH₃)₃]
M_r = 419.11
Monoclinic, P 2₁ /n
a = 11.1058 (4) Å
b = 7.2672 (3) Å
c = 22.5024 (9) Å
= 101.0116 (11)°
V = 1782.69 (12) Å³
Z = 4
Mo K radiation
= 1.55 mm^-1
T = 223 K
0.20 × 0.19 × 0.08 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (REQAB; Jacobson, 1998) T_min = 0.751, T_max = 0.886
17952 measured reflections
4092 independent reflections
3344 reflections with F² > 2.0(F²)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.027
wR(F²) = 0.027
S = 1.07
3344 reflections
223 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.32 e Å^-3
_min = -0.36 e Å^-3

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: CRYSTALS (Watkin et al., 1999); molecular graphics: CrystalStructure; software used to prepare material for publication: CrystalStructure.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5361 ).

Acknowledgements

We acknowledge the Central Research Fund of the University of the Free State for financial assistance.

References

Carruthers, J. R. & Watkin, D. J. (1979). Acta Cryst. A35, 698-699.
Fernandes, R. M., Lang, E. S., Lopez, E. M. V. & De Souza, G. F. (2002). Polyhedron, 21, 1149-1153.
Harrowfield, J. M., Pakawatchai, C. & White, A. H. (1983). J. Chem. Soc. Dalton Trans. pp. 1109-1113.
Herbstein, F. H. & Schwotzer, W. (1984). J. Am. Chem. Soc. 106, 2367-2373.
Irving, H. M. N. H. (1977). Dithizone. London: Chemical Society.
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Kong, F. & Wong, W. (1999). J. Chem. Soc. Dalton Trans. pp. 2497-2501.
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Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.
Schwoerer, H., Von Eschwege, K. G., Bosman, G., Krok, P. & Conradie, J. (2011). ChemPhysChem, pp. 2653-2658.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Von Eschwege, K. G., Conradie, J. & Kuhn, A. (2011a). J. Phys. Chem. A, 115, 14637-14646.
Von Eschwege, K. G., Conradie, J. & Swarts, J. C. (2008). J. Phys. Chem. A, 112, 2211-2218.
Von Eschwege, K. G. & Swarts, J. C. (2010). Polyhedron, 29, 1727-1733.
Von Eschwege, K. G., Van As, L. & Swarts, J. C. (2011b). Electrochim. Acta, 56, 10064-10068.
Watkin, D. J., Prout, C. K., Carruthers, J. R. & Betteridge, P. W. (1999). CRYSTALS. Chemical Crystallography Laboratory, Oxford, England.

metal-organic compounds