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Volume 68 
Part 1 
Pages m79-m80  
January 2012  

Received 13 December 2011
Accepted 14 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.005 Å
Disorder in main residue
R = 0.030
wR = 0.074
Data-to-parameter ratio = 19.6
Details
Open access

Di-n-butylbis(N-ethyl-N-phenyldithiocarbamato-[kappa]S)tin(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(C4H9)2(C9H10NS2)2], features a tetrahedrally coordinated SnIV atom; the dithiocarbamate ligands coordinate in a monodentate fashion, accompanied by two n-butyl chains. The non-coordinating thione S atoms are each proximate to the SnIV atom [3.0136 (7) and 2.9865 (8) Å], giving rise to distortions from the ideal geometry as evident in the wide C-Sn-C bond angle of 139.06 (12) °. In the crystal, C-H...S interactions lead to the formation of a linear supramolecular chain along the b axis. The chains are aligned into layers by C-H...[pi] interactions, and the layers stack along [001]. One of the ethyl groups is statistically disordered over two sets of sites.

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 related structures, see: Awang et al. (2010[Awang, N., Baba, I., Yamin, B. M. & Ng, S. W. (2010). Acta Cryst. E66, m938.]); Kamaludin et al. (2012[Kamaludin, N. F., Baba, I., Awang, N., Mohamed Tahir, M. I. & Tiekink, E. R. T. (2012). Acta Cryst. E68, m62-m63.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C4H9)2(C9H10NS2)2]

  • Mr = 625.51

  • Monoclinic, C 2/c

  • a = 23.9107 (7) Å

  • b = 11.9395 (4) Å

  • c = 22.0117 (7) Å

  • [beta] = 106.766 (3)°

  • V = 6016.8 (3) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 1.14 mm-1

  • T = 150 K

  • 0.30 × 0.23 × 0.18 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 = 0.77, Tmax = 0.81

  • 18598 measured reflections

  • 6072 independent reflections

  • 5190 reflections with I > 2[sigma](I)

  • Rint = 0.028

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

  • wR(F2) = 0.074

  • S = 1.03

  • 6072 reflections

  • 310 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.56 e Å-3

  • [Delta][rho]min = -0.48 e Å-3

Table 1
Selected bond lengths (Å)

Sn-S1 2.5153 (7)
Sn-S3 2.5270 (7)
Sn-C19 2.134 (2)
Sn-C23 2.143 (3)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13-C18 benzene ring.

D-H...A D-H H...A D...A D-H...A
C16-H16...S2i 0.95 2.68 3.550 (4) 152
C26-H26c...Cg1ii 0.98 2.85 3.810 (5) 165
Symmetry codes: (i) x, y+1, z; (ii) [x+{\script{3\over 2}}, y+{\script{5\over 2}}, z+1].

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: HB6565 ).


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. (2010). Acta Cryst. E66, m938.  [CrossRef] [details]
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Kamaludin, N. F., Baba, I., Awang, N., Mohamed Tahir, M. I. & Tiekink, E. R. T. (2012). Acta Cryst. E68, m62-m63.  [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 (2012). E68, m79-m80   [ doi:10.1107/S160053681105392X ]

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