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

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

doi:10.1107/S1600536811053591

Volume 68
Part 1
Pages m62-m63
January 2012

Received 9 December 2011
Accepted 12 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.004 Å
R = 0.022
wR = 0.055
Data-to-parameter ratio = 18.8
Details

(N-Ethyl-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(C₉H₁₀NS₂)], has two independent molecules in the asymmetric unit and each features a tetrahedrally coordinated Sn^IV atom as the dithiocarbamate ligand coordinates in a monodentate fashion. As the non-coordinating thione S atom is proximate to the Sn atom [SnS(thione) = 3.1477 (6) and 2.9970 (5) Å for the independent molecules], distortions from the ideal geometry are evident [the widest angle being 120.48 (5)°]. The most notable feature of the crystal packing is the formation of C-H [pi] interactions that lead to the formation of supramolecular layers parallel to ( $[\overline{3}]$ 2 $[\overline{1}]$ ).

Related literature

For a review on the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008). For the recently reported n-butyl derivative, see: Kamaludin et al. (2011).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₉H₁₀NS₂)]
M_r = 546.29
Triclinic, $[P \overline 1]$
a = 9.6973 (2) Å
b = 12.2804 (2) Å
c = 22.8523 (4) Å
= 90.588 (2)°
= 101.573 (2)°
= 110.687 (2)°
V = 2484.39 (8) Å³
Z = 4
Mo K radiation
= 1.21 mm^-1
T = 150 K
0.30 × 0.24 × 0.19 mm

Data collection

Oxford Diffraction Xcaliber Eos Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.748, T_max = 0.795
62467 measured reflections
10558 independent reflections
9633 reflections with I > 2(I)
R_int = 0.038

Refinement

R[F² > 2(F²)] = 0.022
wR(F²) = 0.055
S = 1.00
10558 reflections
561 parameters
H-atom parameters constrained
_max = 0.55 e Å^-3
_min = -0.44 e Å^-3

Table 1
Selected bond lengths (Å)

Sn1-C10	2.1339 (19)
Sn1-C16	2.1541 (19)
Sn1-C22	2.1210 (18)
Sn1-S1	2.4539 (5)
Sn2-C37	2.1413 (18)
Sn2-C43	2.1605 (19)
Sn2-C49	2.1379 (19)
Sn2-S3	2.4662 (5)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, and Cg3 are the centroids of the C16-C21, C37-C42 and C43-C48 benzene rings, respectively.

D-HA	D-H	HA	DA	D-HA
C9-H9Cg1ⁱ	0.95	2.72	3.630 (3)	160
C25-H25Cg2ⁱⁱ	0.95	2.90	3.639 (3)	135
C32-H32Cg3ⁱⁱⁱ	0.95	2.92	3.824 (2)	160
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) x-1, y, z; (iii) -x+2, -y+2, -z+2.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); 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), DIAMOND (Brandenburg, 2006) and QMol (Gans & Shalloway, 2001); 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: QM2044 ).

Acknowledgements

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

References

Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Gans, J. & Shalloway, D. (2001). J. Mol. Graph. Model. 19, 557-559.
Kamaludin, N. F., Baba, I., Awang, N., Mohamed Tahir, M. I. & Tiekink, E. R. T. (2011). Acta Cryst. E67, m555-m556.
Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, Oxfordshire, 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