(N-Butyl-N-phenyl­dithio­carbamato-κS)triphenyl­tin(IV)

Kamaludin, N.F.; Baba, I.; Awang, N.; Mohamed Tahir, M.I.; Tiekink, E.R.T.

doi:10.1107/S1600536811012426

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 (C-C) = 0.003 Å
R = 0.024
wR = 0.060
Data-to-parameter ratio = 20.4
Details

(N-Butyl-N-phenyldithiocarbamato-S)triphenyltin(IV)

Nurul Farahana Kamaludin,^a Ibrahim Baba,^b ⁺ Normah Awang,^a Mohamed Ibrahim Mohamed Tahir ^c and Edward R. T. Tiekink ^d ^*

^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-HS 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). For a recently reported related structure, see: Awang et al. (2010).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₁₁H₁₄NS₂)]
M_r = 574.34
Monoclinic, P 2₁ /n
a = 10.0488 (1) Å
b = 18.0008 (2) Å
c = 15.2054 (2) Å
= 102.442 (1)°
V = 2685.85 (5) Å³
Z = 4
Mo K radiation
= 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.781, T_max = 0.894
34109 measured reflections
6099 independent reflections
5277 reflections with I > 2(I)
R_int = 0.044

Refinement

R[F² > 2(F²)] = 0.024
wR(F²) = 0.060
S = 1.02
6099 reflections
299 parameters
H-atom parameters constrained
_max = 0.49 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C28-H28S2ⁱ	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); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

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.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tiekink, E. R. T. (2008). Appl. Organomet. Chem. 22, 533-550.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

metal-organic compounds