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Volume 65 
Part 5 
Page m595  
May 2009  

Received 17 April 2009
Accepted 23 April 2009
Online 30 April 2009

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Key indicators
Single-crystal X-ray study
T = 123 K
Mean [sigma](C-C) = 0.008 Å
Disorder in main residue
R = 0.046
wR = 0.139
Data-to-parameter ratio = 21.9
Details
Open access

Bis(N-benzyl-N-isopropyldithiocarbamato-[kappa]S)di-n-butyltin(IV)

Ibrahim Baba,a Nor Syaidatul Akmal,a Normah Awanga and Seik Weng Ngb*

aSchool of Chemical Sciences and Food Technology, Universiti Kebangsaan Malaysia, 43600 Bangi, Selangor Darul Ehsan, Malaysia, and bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

The Sn atom in the title compound, [Sn(C4H9)2(C11H14NS2)2], exists in a tetrahedral C2S2Sn coordination geometry. The geometry is distorted towards skew-trapezoidal-bipyramidal owing to the proximity of the double-bonded S atoms. The C2Sn angles range from 129.0 (2) to 136.9 (2)°, the covalent Sn-S lengths from 2.529 (1) to 2.544 (1) Å, and the dative Sn[leftwards arrow]S lengths from 2.831 (1) to 3.042 (1) Å in the five independent molecules comprising the asymmetric unit. Two of the butyl groups were modelled over two positions of equal occupancy. All butyl groups were refined with distance restraints.

Related literature

For other di-n-butyltin dithiocarbamates, see: Farina et al. (2000[Farina, Y., Baba, I., Othman, A. H. & Ng, S. W. (2000). Main Group Met. Chem. 23, 795-796.]); Lokaj et al. (1986[Lokaj, J., Kellö, E., Kettmann, V., Vrábel, V. & Rattay, V. (1986). Collect. Czech. Chem. Commun. 51, 2521-2527.]); Menezes et al. (2005[Menezes, D. C., Vieira, F. T., de Lima, G. M., Porto, A. O., Cortes, M. E., Ardisson, J. D. & Albrecht-Schmitt, T. E. (2005). Eur. J. Med. Chem. 40, 1277-1282.]); Vrábel et al. (1992a[Vrábel, V., Lokaj, J., Kellö, E., Rattay, V., Batsanov, A. C. & Struchkov, Yu. T. (1992a). Acta Cryst. C48, 627-629.],b[Vrábel, V., Lokaj, J., Kellö, E., Garaj, J., Batsanov, A. C. & Struchkov, Yu. T. (1992b). Acta Cryst. C48, 633-635.]); Vrábel & Kellö (1993[Vrábel, V. & Kellö, E. (1993). Acta Cryst. C49, 873-875.]); Zia-ur-Rehman et al. (2006[Zia-ur-Rehman, Shahzadi, S., Ali, S., Badshah, A. & Jin, G.-X. (2006). J. Iran. Chem. Soc. 3, 157-160.]). For a review of the applications and structures of tin dithiocarbamates, see: Tiekink (2008[Tiekink, E. R. T. (2008). Appl. Organomet. Chem. 22, 533-550.]).

[Scheme 1]

Experimental

Crystal data

  • [Sn(C4H9)2(C11H14NS2)2]

  • Mr = 681.62

  • Triclinic, [P \overline 1]

  • a = 17.7745 (2) Å

  • b = 19.5463 (3) Å

  • c = 26.2062 (4) Å

  • [alpha] = 102.5254 (7)°

  • [beta] = 95.1492 (7)°

  • [gamma] = 110.2569 (8)°

  • V = 8202.1 (2) Å3

  • Z = 10

  • Mo K[alpha] radiation

  • [mu] = 1.06 mm-1

  • T = 123 K

  • 0.30 × 0.30 × 0.10 mm
Data collection

  • Bruker SMART APEX diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.743, Tmax = 0.902

  • 67722 measured reflections

  • 36923 independent reflections

  • 23409 reflections with I > 2[sigma](I)

  • Rint = 0.028
Refinement

  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.139

  • S = 1.15

  • 36923 reflections

  • 1684 parameters

  • 96 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 2.53 e Å-3

  • [Delta][rho]min = -1.45 e Å-3

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; 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: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2009[Westrip, S. P. (2009). publCIF. In preparation.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK2429 ).

Acknowledgements

We thank Universiti Kebangsaan Malaysia and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.  [CrossRef] [ChemPort]
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farina, Y., Baba, I., Othman, A. H. & Ng, S. W. (2000). Main Group Met. Chem. 23, 795-796.
Lokaj, J., Kellö, E., Kettmann, V., Vrábel, V. & Rattay, V. (1986). Collect. Czech. Chem. Commun. 51, 2521-2527.
Menezes, D. C., Vieira, F. T., de Lima, G. M., Porto, A. O., Cortes, M. E., Ardisson, J. D. & Albrecht-Schmitt, T. E. (2005). Eur. J. Med. Chem. 40, 1277-1282.  [ISI] [CSD] [CrossRef] [PubMed]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
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]
Vrábel, V., Lokaj, J., Kellö, E., Rattay, V., Batsanov, A. C. & Struchkov, Yu. T. (1992a). Acta Cryst. C48, 627-629.  [CrossRef] [details]
Vrábel, V., Lokaj, J., Kellö, E., Garaj, J., Batsanov, A. C. & Struchkov, Yu. T. (1992b). Acta Cryst. C48, 633-635.  [CrossRef] [details]
Vrábel, V. & Kellö, E. (1993). Acta Cryst. C49, 873-875.  [CrossRef] [details]
Westrip, S. P. (2009). publCIF. In preparation.
Zia-ur-Rehman, Shahzadi, S., Ali, S., Badshah, A. & Jin, G.-X. (2006). J. Iran. Chem. Soc. 3, 157-160.

Acta Cryst (2009). E65, m595  [ doi:10.1107/S1600536809015116 ]

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