catena-Poly[[triphenyl­tin(IV)]-μ-2-(cyclo­hexyl­amino­carbon­yl)benzoato-κ2O1:O2]

Imtiaz-ud-Din; Raqiqt-ul-Rasool; Bhatti, M.H.; Ng, S.W.

doi:10.1107/S1600536810026978

Volume 66
Part 8
Page m931
August 2010

Received 7 July 2010
Accepted 7 July 2010
Online 14 July 2010

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.002 Å
R = 0.019
wR = 0.049
Data-to-parameter ratio = 18.2
Details

catena-Poly[[triphenyltin(IV)]--2-(cyclohexylaminocarbonyl)benzoato-²O¹:O²]

Imtiaz-ud-Din,^a Raqiqt-ul-Rasool,^a Moazzam H. Bhatti ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Allama Iqbal Open University, H/8 Islamabad, Pakistan, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
Correspondence e-mail: seikweng@um.edu.my

In the title polymeric complex, [Sn(C₆H₅)₃(C₁₄H₁₆NO₃)]_n, adjacent triphenyltin cations are bridged by the N-cyclohexylphthalamate anion through the carboxylate and carbonyl O atoms, forming a helical chain running along the b axis. The amide N atom is a hydrogen-bond donor to the uncoordinated carboxylate O atom. The geometry at the five-coordinate Sn atom is trans-C₃SnO₂ trigonal-bipyramidal.

Related literature

For a review on organotin carboxylates, see: Tiekink (1991, 1994). Triphenyltin arylcarboxylates generally exist as monomeric molecules; see: Ng et al. (1986). For the synthesis of N-cyclohexylphthalamic acid, see: Dolzhenko et al. (2003).

Experimental

Crystal data

[Sn(C₆H₅)₃(C₁₄H₁₆NO₃)]
M_r = 596.27
Monoclinic, P 2₁ /n
a = 9.8574 (5) Å
b = 16.0734 (8) Å
c = 17.1669 (8) Å
= 99.447 (1)°
V = 2683.1 (2) Å³
Z = 4
Mo K radiation
= 0.99 mm^-1
T = 100 K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.694, T_max = 0.827
25326 measured reflections
6165 independent reflections
5710 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.019
wR(F²) = 0.049
S = 1.02
6165 reflections
338 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
_max = 0.35 e Å^-3
_min = -0.50 e Å^-3

Table 1
Selected geometric parameters (Å, °)

Sn1-C1	2.130 (1)
Sn1-C7	2.129 (2)
Sn1-C13	2.119 (1)
Sn1-O1	2.149 (1)
Sn1-O3ⁱ	2.392 (1)

O1-Sn1-O3ⁱ	174.06 (4)
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Table 2
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O2	0.86 (1)	1.85 (1)	2.666 (2)	158 (2)

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 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: XU2796 ).

Acknowledgements

We thank Allama Iqbal Open University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Dolzhenko, A. V., Syropyatov, B. Ya., Koz'minykh, V. O., Kolotova, N. V., Zakhmatov, A. V. & Borodin, A. Yu. (2003). Pharm. Chem. J. 37, 407-408.
Ng, S. W., Chen, W. & Kumar Das, V. G. (1986). J. Organomet. Chem. 345, 59-64.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1-23.
Tiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71-116.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

metal-organic compounds

catena-Poly[[triphenyltin(IV)]--2-(cyclohexylaminocarbonyl)benzoato-2O1:O2]