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Volume 67 
Part 5 
Pages m555-m556  
May 2011  

Received 3 April 2011
Accepted 4 April 2011
Online 7 April 2011

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.003 Å
R = 0.024
wR = 0.060
Data-to-parameter ratio = 20.4
Details
Open access

(N-Butyl-N-phenyldithiocarbamato-[kappa]S)triphenyltin(IV)

aEnvironmental Health Programme, Faculty of Allied Health Sciences, Universiti Kebangsaan Malaysia, Jalan Raja Muda Aziz, 50300 Kuala Lumpur, Malaysia,bSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Malaysia,cDepartment of Chemistry, Universiti Putra Malaysia, 43400 Serdang, Malaysia, and dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The title compound, [Sn(C6H5)3(C11H14NS2)], features a tetrahedrally coordinated Sn atom, as the dithiocarbamate ligand coordinates in a monodentate fashion. Due to the proximity of the non-coordinating thione S atom, distortions from ideal tetrahedral geometry about the metal atom are evident with the widest C-Sn-S angle being 117.26 (5)°. In the crystal, molecules are linked by C-H...S interactions, which generate helical supramolecular chains along the b axis.

Related literature

For a review on the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008[Tiekink, E. R. T. (2008). Appl. Organomet. Chem. 22, 533-550.]). For a recently reported related structure, see: Awang et al. (2010[Awang, N., Baba, I., Yamin, B. M., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, m1144.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H5)3(C11H14NS2)]

  • Mr = 574.34

  • Monoclinic, P 21 /n

  • a = 10.0488 (1) Å

  • b = 18.0008 (2) Å

  • c = 15.2054 (2) Å

  • [beta] = 102.442 (1)°

  • V = 2685.85 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.12 mm-1

  • T = 150 K

  • 0.24 × 0.22 × 0.10 mm

Data collection
  • Oxford Diffraction Xcaliber Eos Gemini diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.781, Tmax = 0.894

  • 34109 measured reflections

  • 6099 independent reflections

  • 5277 reflections with I > 2[sigma](I)

  • Rint = 0.044

Refinement
  • R[F2 > 2[sigma](F2)] = 0.024

  • wR(F2) = 0.060

  • S = 1.02

  • 6099 reflections

  • 299 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.49 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Selected geometric parameters (Å, °)

Sn-S1 2.4772 (5)
Sn-S2 3.1048 (5)
Sn-C12 2.1286 (18)
Sn-C18 2.1380 (19)
Sn-C24 2.1521 (18)
S1-C1 1.758 (2)
S2-C1 1.675 (2)
C12-Sn-C18 113.76 (7)
C12-Sn-C24 107.51 (7)
C18-Sn-C24 107.45 (7)
C12-Sn-S1 117.26 (5)
C18-Sn-S1 115.54 (5)
C24-Sn-S1 92.18 (5)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C28-H28...S2i 0.95 2.83 3.612 (2) 140
Symmetry code: (i) [-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.]) and DIAMOND (Brandenburg, 2006[Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5836 ).


Acknowledgements

The authors thank Universiti Kebangsaan Malaysia (UKM-GUP-NBT-08-27-111), the Ministry of Higher Education (UKM-ST-06-FRGS0092-2010), Universiti Putra Malaysia and the University of Malaya for supporting this study.

References

Awang, N., Baba, I., Yamin, B. M., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, m1144.  [CrossRef] [details]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tiekink, E. R. T. (2008). Appl. Organomet. Chem. 22, 533-550.  [ISI] [CrossRef] [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2011). E67, m555-m556   [ doi:10.1107/S1600536811012426 ]

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