(N-sec-Butyl-N-n-propyl­dithio­carbamato-κ2S,S′)triphenyl­tin(IV)

Awang, N.; Baba, I.; Yamin, B.M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536810033039

Volume 66
Part 9
Page m1144
September 2010

Received 16 August 2010
Accepted 17 August 2010
Online 21 August 2010

Key indicators
Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R = 0.032
wR = 0.083
Data-to-parameter ratio = 21.9
Details

(N-sec-Butyl-N-n-propyldithiocarbamato-²S,S')triphenyltin(IV)

Normah Awang,^a Ibrahim Baba,^a Bohari M. Yamin,^a Seik Weng Ng ^b and Edward R. T. Tiekink ^b ^*

^aSchool of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangbaan Malaysia, 43600 Bangi, Malaysia, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: edward.tiekink@gmail.com

The Sn atom in the title compound, [Sn(C₆H₅)₃(C₈H₁₆NS₂)], is pentacoordinated by two S atoms, derived from an asymmetrically coordinating dithiocarbamate ligand, and three ipso-C atoms. The coordination geometry is intermediate between square-pyramidal and trigonal-bipyramidal, with a leaning towards the latter. The presence of close intramolecular C-HS contacts preclude the S atoms from forming significant intermolecular interactions. Rather, molecules are consolidated in the crystal structure by C-H [pi] interactions.

Related literature

For a review of the applications and structural chemistry of tin dithiocarbamates, see: Tiekink (2008). For a related organotin structure having the same dithiocarbamate ligand, see: Abdul Muthalib et al. (2010). For additional structural analysis, see: Addison et al. (1984).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₈H₁₆NS₂)]
M_r = 540.33
Monoclinic, C 2/c
a = 14.7997 (5) Å
b = 12.1844 (5) Å
c = 28.8891 (11) Å
= 97.348 (1)°
V = 5166.7 (3) Å³
Z = 8
Mo K radiation
= 1.16 mm^-1
T = 293 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.653, T_max = 0.801
17218 measured reflections
5923 independent reflections
5179 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.083
S = 1.02
5923 reflections
271 parameters
H-atom parameters constrained
_max = 0.70 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1-C6 and C7-C12 rings, respectively.

D-HA	D-H	HA	DA	D-HA
C14-H14S2	0.93	2.75	3.433 (3)	131
C20-H20S2	0.98	2.49	3.059 (3)	117
C24-H24aS1	0.97	2.58	2.938 (3)	102
C25-H25bS1	0.97	2.84	3.360 (4)	115
C16-H16Cg1ⁱ	0.93	2.78	3.618 (3)	151
C23-H23aCg2ⁱⁱ	0.96	2.91	3.773 (4)	150
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009); 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: HG2701 ).

Acknowledgements

We thank UKM (UKM-GUP-NBT-08-27-111 and UKM-ST-06-FRGS0092-2010) and the University of Malaya for supporting this study.

References

Abdul Muthalib, A. F., Baba, I., Mohamed Tahir, M. I., Ng, S. W. & Tiekink, E. R. T. (2010). Acta Cryst. E66, m1087.
Addison, A. W., Rao, T. N., Reedijk, J., van Rijn, J. & Verschoor, G. C. (1984). J. Chem. Soc. Dalton Trans. pp. 1349-1356.
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2002). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Tiekink, E. R. T. (2008). Appl. Organomet. Chem. 22, 533-550.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

metal-organic compounds

(N-sec-Butyl-N-n-propyldithiocarbamato-2S,S')triphenyltin(IV)