[Journal logo]

Volume 69 
Part 8 
Pages m473-m474  
August 2013  

Received 2 July 2013
Accepted 12 July 2013
Online 27 July 2013

Key indicators
Single-crystal X-ray study
T = 115 K
Mean [sigma](C-C) = 0.006 Å
R = 0.035
wR = 0.083
Data-to-parameter ratio = 21.8
Details
Open access

Bis(cyclohexylammonium) tetrachlorido(oxalato)stannate(IV)

aLaboratoire de Chimie Minérale et Analytique (LACHIMIA), Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and bICMUB UMR 6302, Université de Bourgogne, Faculté des Sciences, 9 avenue Alain Savary, 21000 Dijon, France
Correspondence e-mail: diasseam@yahoo.fr, hcattey@u-bourgogne.fr

The title salt, (C6H14N)2[Sn(C2O4)Cl4], was obtained as a by-product from the reaction between 2C6H14N+·C2O42-·1.5H2O and SnCl2·2H2O. The cyclohexylammonium cation has a chair conformation. The complex anion consists of an oxalate anion chelating the SnCl4 moiety, resulting in a distorted octahedral coordination sphere of the SnIV atom with the O atoms in equatorial cis positions. In the crystal, cations and anions are linked through N-H...O and N-H...Cl interactions into a layered arrangement parallel to (100).

Related literature

For applications of organotin(IV) compounds, see: Evans & Karpel (1985[Evans, C. J. & Karpel, S. (1985). Organotin Compounds in Modern Technology. J. Organomet. Chem. Library, Vol. 16. Amsterdam: Elsevier.]). For background to organotin(IV) chemistry, see: Ballmann et al. (2009[Ballmann, J., Fuchs, M. G. G., Dechert, S., John, M. & Meyer, F. (2009). Inorg. Chem. 48, 90-99.]); Meriem et al. (1989[Meriem, A., Gielen, M. & Willem, R. (1989). J. Organomet. Chem. 365, 91-101.]); Ng & Kumar Das (1997[Ng, S. W. & Kumar Das, V. G. (1997). Acta Cryst. C53, 1034-1036.]); Yin & Wang (2004[Yin, H.-D. & Wang, C.-H. (2004). Appl. Organomet. Chem. 18, 411-412.]); Zhang et al. (2006[Zhang, W.-L., Ma, J.-F. & Jiang, H. (2006). Acta Cryst. E62, m460-m461.]). For background to halogenidotin(IV) chemistry, see: Sarr & Diop (1990[Sarr, O. & Diop, L. (1990). Spectrochim. Acta Part A, 46, 1239-1244.]); Qamar-Kane & Diop (2010[Qamar-Kane, H. & Diop, L. (2010). St. Cerc. St. CICBIA, 11, 389-392.]); Willey et al. (1998[Willey, G. R., Woodman, T. J., Deeth, R. J. & Errington, W. (1998). Main Group Met. Chem. 21, 583-591.]); Diallo et al. (2009[Diallo, W., Diassé-Sarr, A. D., Diop, L., Mahieu, B., Biesemans, M., Willem, R., Kociok-Köhn, G. & Molloy, K. C. (2009). St. Cerc. St. CICBIA, 10, 207-212.]). For related crystal structures with an oxalatotin(IV) moiety, see: Skapski et al. (1974[Skapski, A. C., Guerchais, J.-E. & Calves, J.-Y. (1974). C. R. Acad. Sci. Ser. C Chim. 278, 1377-1379.]); Gueye et al. (2012[Gueye, N., Diop, L., Molloy, K. C. & Kociok-Köhn, G. (2012). Acta Cryst. E68, m854-m855.]); Sow et al. (2010[Sow, Y., Diop, L., Kociok-Köhn, G. & Molloy, K. C. (2010). Main Group Met. Chem. 33, 205-208.], 2013[Sow, Y., Diop, L., Molloy, K. C. & Kociok-Köhn, G. (2013). Acta Cryst. E69, m106-m107.]).

[Scheme 1]

Experimental

Crystal data
  • (C6H14N)2[Sn(C2O4)Cl4]

  • Mr = 548.87

  • Monoclinic, P 21 /c

  • a = 11.2293 (9) Å

  • b = 15.715 (1) Å

  • c = 12.8464 (10) Å

  • [beta] = 93.238 (2)°

  • V = 2263.4 (3) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 1.62 mm-1

  • T = 115 K

  • 0.17 × 0.08 × 0.03 mm

Data collection
  • Nonius KappaCCD diffractometer

  • Absorption correction: multi-scan (Blessing, 1995[Blessing, R. H. (1995). Acta Cryst. A51, 33-38.]) Tmin = 0.770, Tmax = 0.953

  • 9402 measured reflections

  • 4979 independent reflections

  • 4503 reflections with I > 2[sigma](I)

  • Rint = 0.025

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.083

  • S = 1.12

  • 4979 reflections

  • 228 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.03 e Å-3

  • [Delta][rho]min = -0.99 e Å-3

Table 1
Selected bond lengths (Å)

Sn1-O2 2.121 (2)
Sn1-O1 2.155 (2)
Sn1-Cl3 2.3547 (9)
Sn1-Cl2 2.3667 (9)
Sn1-Cl1 2.3794 (9)
Sn1-Cl4 2.4407 (8)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O4 0.89 1.97 2.853 (3) 169
N1-H1B...O1i 0.89 2.18 3.038 (4) 163
N1-H1C...O3ii 0.89 2.01 2.875 (4) 162
N2-H2A...O4 0.89 2.25 2.887 (4) 129
N2-H2A...Cl4i 0.89 2.78 3.315 (3) 120
N2-H2B...Cl4iii 0.89 2.38 3.262 (3) 169
N2-H2C...O3 0.89 2.02 2.869 (4) 158
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}].

Data collection: COLLECT (Nonius, 1998[Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.]); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: DENZO-SMN; program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and Mercury (Macrae et al., 2006[Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: WM2756 ).


Acknowledgements

The authors gratefully acknowledge the Cheikh Anta Diop University of Dakar (Senegal), the Centre National de la Recherche Scientifique (CNRS, France) and the University of Burgundy (Dijon, France).

References

Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.  [CrossRef] [Web of Science] [IUCr Journals]
Ballmann, J., Fuchs, M. G. G., Dechert, S., John, M. & Meyer, F. (2009). Inorg. Chem. 48, 90-99.  [Web of Science] [CSD] [CrossRef] [PubMed] [ChemPort]
Blessing, R. H. (1995). Acta Cryst. A51, 33-38.  [CrossRef] [IUCr Journals]
Diallo, W., Diassé-Sarr, A. D., Diop, L., Mahieu, B., Biesemans, M., Willem, R., Kociok-Köhn, G. & Molloy, K. C. (2009). St. Cerc. St. CICBIA, 10, 207-212.  [ChemPort]
Evans, C. J. & Karpel, S. (1985). Organotin Compounds in Modern Technology. J. Organomet. Chem. Library, Vol. 16. Amsterdam: Elsevier.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Gueye, N., Diop, L., Molloy, K. C. & Kociok-Köhn, G. (2012). Acta Cryst. E68, m854-m855.  [CrossRef] [ChemPort] [IUCr Journals]
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453-457.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Meriem, A., Gielen, M. & Willem, R. (1989). J. Organomet. Chem. 365, 91-101.  [CrossRef] [ChemPort]
Ng, S. W. & Kumar Das, V. G. (1997). Acta Cryst. C53, 1034-1036.  [CrossRef] [IUCr Journals]
Nonius (1998). COLLECT. Nonius BV, Delft, The Netherlands.
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.
Qamar-Kane, H. & Diop, L. (2010). St. Cerc. St. CICBIA, 11, 389-392.
Sarr, O. & Diop, L. (1990). Spectrochim. Acta Part A, 46, 1239-1244.  [CrossRef]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Skapski, A. C., Guerchais, J.-E. & Calves, J.-Y. (1974). C. R. Acad. Sci. Ser. C Chim. 278, 1377-1379.  [ChemPort]
Sow, Y., Diop, L., Kociok-Köhn, G. & Molloy, K. C. (2010). Main Group Met. Chem. 33, 205-208.  [CrossRef] [ChemPort]
Sow, Y., Diop, L., Molloy, K. C. & Kociok-Köhn, G. (2013). Acta Cryst. E69, m106-m107.  [CrossRef] [ChemPort] [IUCr Journals]
Willey, G. R., Woodman, T. J., Deeth, R. J. & Errington, W. (1998). Main Group Met. Chem. 21, 583-591.  [CrossRef] [ChemPort]
Yin, H.-D. & Wang, C.-H. (2004). Appl. Organomet. Chem. 18, 411-412.  [Web of Science] [CSD] [CrossRef] [ChemPort]
Zhang, W.-L., Ma, J.-F. & Jiang, H. (2006). Acta Cryst. E62, m460-m461.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, m473-m474   [ doi:10.1107/S1600536813019284 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.