n-Butyldichlorido{4-cyclo­hexyl-1-[1-(pyridin-2-yl-κN)ethyl­idene]thio­semi­carb­azi­dato-κ2N1,S}tin(IV)

Affan, M.A.; Salam, M.A.; Asaruddin, M.R.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812025937

Volume 68
Part 7
Pages m909-m910
July 2012

Received 5 June 2012
Accepted 7 June 2012
Online 16 June 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.005 Å
R = 0.035
wR = 0.085
Data-to-parameter ratio = 20.9
Details

n-Butyldichlorido{4-cyclohexyl-1-[1-(pyridin-2-yl-N)ethylidene]thiosemicarbazidato-²N¹,S}tin(IV)

Md. Abu Affan,^a Md. Abdus Salam,^a Mohd Razip Asaruddin,^a Seik Weng Ng ^b,^c and Edward R. T. Tiekink ^b ^*

^aFaculty of Resource Science and Technology, Universiti Malaysia Sarawak, 94300 Kota Samaharan, Sawarak, Malaysia,^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^cChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
Correspondence e-mail: Edward.Tiekink@gmail.com

Two independent molecules comprise the asymmetric unit in the title compound, [Sn(C₄H₉)(C₁₄H₁₉N₄S)Cl₂]. In each molecule, the Sn^IV atom exists within a distorted octahedral geometry defined by the N,N',S-tridentate mono-deprotonated Schiff base ligand, two mutually trans Cl atoms, and the [alpha] -C atom of the n-butyl group; the latter is trans to the azo-N atom. The greatest distortion from the ideal geometry is found in the nominally trans angle formed by the S and pyridyl-N atoms at Sn [151.72 (7) and 152.04 (7)°, respectively]. In the crystal, molecules are consolidated into a three-dimensional architecture by a combination of N-HCl, C-H [pi] and [pi] - [pi] interactions [inter-centroid distances = 3.6718 (19) and 3.675 (2) Å].

Related literature

For the structures of the methyltin and phenyltin derivatives, see: Salam et al. (2010a,b).

Experimental

Crystal data

[Sn(C₄H₉)(C₁₄H₁₉N₄S)Cl₂]
M_r = 522.09
Monoclinic, P 2₁ /n
a = 12.1229 (3) Å
b = 15.4518 (4) Å
c = 23.6868 (6) Å
= 103.894 (3)°
V = 4307.21 (19) Å³
Z = 8
Mo K radiation
= 1.54 mm^-1
T = 100 K
0.25 × 0.25 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) T_min = 0.794, T_max = 1.000
18205 measured reflections
9861 independent reflections
8503 reflections with I > 2(I)
R_int = 0.024

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.085
S = 1.04
9860 reflections
471 parameters
H-atom parameters constrained
_max = 1.64 e Å^-3
_min = -1.11 e Å^-3

Table 1
Selected bond lengths (Å)

Sn1-C1	2.187 (3)
Sn1-N1	2.269 (2)
Sn1-N2	2.209 (2)
Sn1-S1	2.4785 (8)
Sn1-Cl1	2.5123 (8)
Sn1-Cl2	2.4959 (8)
Sn2-C19	2.182 (3)
Sn2-N5	2.255 (3)
Sn2-N6	2.215 (3)
Sn2-S2	2.4806 (8)
Sn2-Cl3	2.4959 (8)
Sn2-Cl4	2.5124 (8)

Table 2
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1,C5-C9 ring.

D-HA	D-H	HA	DA	D-HA
N4-H4Cl3	0.88	2.65	3.516 (3)	167
C15-H15ACg1ⁱ	0.99	2.85	3.692 (4)	143
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: CrysAlis PRO (Agilent, 2012); 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), QMol (Gans & Shalloway, 2001) 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: QM2072 ).

Acknowledgements

This work was supported financially by the Ministry of Science Technology and Innovation (MOSTI) under research grant No. 06-01-09-SF0046. The authors would like to thank Universiti Malaysia Sarawak (UNIMAS) for the facilities to carry out the research work. They also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
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.
Salam, M. A., Affan, M. A., Ahmad, F. B., Tahir, M. I. M. & Tiekink, E. R. T. (2010a). Acta Cryst. E66, m1503-m1504.
Salam, M. A., Affan, M. A., Shamsuddin, M. & Ng, S. W. (2010b). Acta Cryst. E66, m570.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.