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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 [sigma](C-C) = 0.003 Å
R = 0.027
wR = 0.027
Data-to-parameter ratio = 15.0
Details
Open access

(1,5-Diphenylthiocarbazonato-[kappa]S)trimethyltin(IV)

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 SnIV 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[Irving, H. M. N. H. (1977). Dithizone. London: Chemical Society.]). For the synthesis of dithizone, see: Pelkis et al. (1957[Pelkis, P. S., Dubenko, R. G. & Pupko, L. S. (1957). J. Org. Chem. USSR. 27, 2190-2194.]). For structural aspects of dithizone and its oxidation products and observed solvatochromism and concentratochromism, see: Von Eschwege et al. (2011a[Von Eschwege, K. G., Conradie, J. & Kuhn, A. (2011a). J. Phys. Chem. A, 115, 14637-14646.]). For related ligand and complex structures, see: Harrowfield et al. (1983[Harrowfield, J. M., Pakawatchai, C. & White, A. H. (1983). J. Chem. Soc. Dalton Trans. pp. 1109-1113.]); Kong & Wong (1999[Kong, F. & Wong, W. (1999). J. Chem. Soc. Dalton Trans. pp. 2497-2501.]); Herbstein & Schwotzer (1984[Herbstein, F. H. & Schwotzer, W. (1984). J. Am. Chem. Soc. 106, 2367-2373.]); Fernandes et al. (2002[Fernandes, R. M., Lang, E. S., Lopez, E. M. V. & De Souza, G. F. (2002). Polyhedron, 21, 1149-1153.]); Von Eschwege et al. (2008[Von Eschwege, K. G., Conradie, J. & Swarts, J. C. (2008). J. Phys. Chem. A, 112, 2211-2218.]); Laing et al. (1971[Laing, M., Sommerville, P. & Alsop, P. A. (1971). J. Chem. Soc. A, pp. 1247-1251.]). For electrochemical studies of dithizone and its Hg complex, see: Von Eschwege & Swarts (2010[Von Eschwege, K. G. & Swarts, J. C. (2010). Polyhedron, 29, 1727-1733.]); Von Eschwege et al. (2011b[Von Eschwege, K. G., Van As, L. & Swarts, J. C. (2011b). Electrochim. Acta, 56, 10064-10068.]). For femto second laser spectroscopy studies on a photochromic dithizonatomercury complex, see: Schwoerer et al. (2011[Schwoerer, H., Von Eschwege, K. G., Bosman, G., Krok, P. & Conradie, J. (2011). ChemPhysChem, pp. 2653-2658.]). For the weighting scheme, see: Carruthers & Watkin (1979[Carruthers, J. R. & Watkin, D. J. (1979). Acta Cryst. A35, 698-699.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C13H11N4S)(CH3)3]

  • Mr = 419.11

  • Monoclinic, P 21 /n

  • a = 11.1058 (4) Å

  • b = 7.2672 (3) Å

  • c = 22.5024 (9) Å

  • [beta] = 101.0116 (11)°

  • V = 1782.69 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.751, Tmax = 0.886

  • 17952 measured reflections

  • 4092 independent reflections

  • 3344 reflections with F2 > 2.0[sigma](F2)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.32 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Data collection: PROCESS-AUTO (Rigaku, 1998[Rigaku (1998). PROCESS-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002[Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC Inc., The Woodlands, Texas, USA.]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: CRYSTALS (Watkin et al., 1999[Watkin, D. J., Prout, C. K., Carruthers, J. R. & Betteridge, P. W. (1999). CRYSTALS. Chemical Crystallography Laboratory, Oxford, England.]); 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.  [CrossRef] [details]
Fernandes, R. M., Lang, E. S., Lopez, E. M. V. & De Souza, G. F. (2002). Polyhedron, 21, 1149-1153.  [ISI] [CSD] [CrossRef] [ChemPort]
Harrowfield, J. M., Pakawatchai, C. & White, A. H. (1983). J. Chem. Soc. Dalton Trans. pp. 1109-1113.  [CrossRef]
Herbstein, F. H. & Schwotzer, W. (1984). J. Am. Chem. Soc. 106, 2367-2373.  [CrossRef] [ChemPort] [ISI]
Irving, H. M. N. H. (1977). Dithizone. London: Chemical Society.
Jacobson, R. (1998). REQAB. Private communication to the Rigaku Corporation, Tokyo, Japan.
Kong, F. & Wong, W. (1999). J. Chem. Soc. Dalton Trans. pp. 2497-2501.  [CSD] [CrossRef]
Laing, M., Sommerville, P. & Alsop, P. A. (1971). J. Chem. Soc. A, pp. 1247-1251.
Pelkis, P. S., Dubenko, R. G. & Pupko, L. S. (1957). J. Org. Chem. USSR. 27, 2190-2194.
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.  [ISI] [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Von Eschwege, K. G., Conradie, J. & Kuhn, A. (2011a). J. Phys. Chem. A, 115, 14637-14646.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Von Eschwege, K. G., Conradie, J. & Swarts, J. C. (2008). J. Phys. Chem. A, 112, 2211-2218.  [ISI] [CrossRef] [PubMed] [ChemPort]
Von Eschwege, K. G. & Swarts, J. C. (2010). Polyhedron, 29, 1727-1733.  [ISI] [CrossRef] [ChemPort]
Von Eschwege, K. G., Van As, L. & Swarts, J. C. (2011b). Electrochim. Acta, 56, 10064-10068.  [ISI] [CrossRef] [ChemPort]
Watkin, D. J., Prout, C. K., Carruthers, J. R. & Betteridge, P. W. (1999). CRYSTALS. Chemical Crystallography Laboratory, Oxford, England.


Acta Cryst (2012). E68, m1518  [ doi:10.1107/S1600536812047216 ]

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