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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 [sigma](C-C) = 0.002 Å
R = 0.019
wR = 0.049
Data-to-parameter ratio = 18.2
Details
Open access

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

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[Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1-23.], 1994[Tiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71-116.]). Triphenyltin arylcarboxylates generally exist as monomeric molecules; see: Ng et al. (1986[Ng, S. W., Chen, W. & Kumar Das, V. G. (1986). J. Organomet. Chem. 345, 59-64.]). For the synthesis of N-cyclohexylphthalamic acid, see: Dolzhenko et al. (2003[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.]).

[Scheme 1]

Experimental

Crystal data
  • [Sn(C6H5)3(C14H16NO3)]

  • Mr = 596.27

  • Monoclinic, P 21 /n

  • a = 9.8574 (5) Å

  • b = 16.0734 (8) Å

  • c = 17.1669 (8) Å

  • [beta] = 99.447 (1)°

  • V = 2683.1 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.694, Tmax = 0.827

  • 25326 measured reflections

  • 6165 independent reflections

  • 5710 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.35 e Å-3

  • [Delta][rho]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-H...A D-H H...A D...A D-H...A
N1-H1...O2 0.86 (1) 1.85 (1) 2.666 (2) 158 (2)

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: X-SEED (Barbour, 2001[Barbour, L. J. (2001). J. Supramol. Chem. 1, 189-191.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


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.  [CrossRef] [ChemPort]
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.  [CrossRef] [ChemPort]
Ng, S. W., Chen, W. & Kumar Das, V. G. (1986). J. Organomet. Chem. 345, 59-64.  [CrossRef]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Tiekink, E. R. T. (1991). Appl. Organomet. Chem. 5, 1-23.  [CrossRef] [ChemPort] [ISI]
Tiekink, E. R. T. (1994). Trends Organomet. Chem. 1, 71-116.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2010). E66, m931  [ doi:10.1107/S1600536810026978 ]

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