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Volume 69 
Part 4 
Pages m187-m188  
April 2013  

Received 1 February 2013
Accepted 21 February 2013
Online 6 March 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.008 Å
R = 0.026
wR = 0.064
Data-to-parameter ratio = 19.9
Details
Open access

2-Methoxyanilinium trichloridostannate(II)

aLaboratoire de Génie des Matériaux et Environnement, École Nationale d'Ingénieurs de Sfax, BP 1173, Sfax, Tunisia, and bService commun d'analyse par diffraction des rayons X, Université de Brest, 6 Avenue Victor Le Gorgeu, CS 93837, F-29238 Brest Cedex 3, France
Correspondence e-mail: slah.kamoun@gmail.com

The title compound, (C7H10NO)[SnCl3], is a new compound with non-linear optical (NLO) properties. The structure is pseudocentrosymmetric; the absence of an inversion centre was proved by the Kurtz and Perry method showing a significant second harmonic generation (SHG) signal about ten times lower than that from potassium dihydrogenphosphate. The crystal structure exhibits alternating organic and inorganic layers parallel to the ab plane, which are stabilized by intermolecular N-H...Cl interactions.

Related literature

For related structures, see: Zhang et al. (2009[Zhang, S. J., Lanty, G., Lauret, J. S., Deleporte, E., Audebert, P. & Galmiche, L. (2009). Acta Mater. 57, 3301-3309.]). For the effects of substituents on the internal angles of the benzene ring, see: Domenicano & Murray-Rust (1979[Domenicano, A. & Murray-Rust, P. (1979). Tetrahedron Lett. 20, 2283-2286.]). For NLO and SHG, see: Kurtz & Perry (1968[Kurtz, S. K. & Perry, T. T. (1968). J. Appl. Phys. 39, 798-3813.]); Kamoun et al. (1995[Kamoun, S., Daoud, A., Elfakir, A., Quarton, M. & Ledoux, I. (1995). Solid State Commun. 94, 893-897.]). For ferroelectricity of related compounds, see: Ben Gozlen et al. (1994[Ben Gozlen, M. H., Kamoun, S., Paulush, H. & Pabst, I. (1994). Z. Kristallogr. 209, 382-382.]). For electric and dielectric properties of related compounds, see: Karoui et al. (2013[Karoui, S., Kamoun, S. & Jouini, A. (2013). J. Solid State Chem. 197, 60-68.]).

[Scheme 1]

Experimental

Crystal data
  • (C7H10NO)[SnCl3]

  • Mr = 349.20

  • Orthorhombic, P 21 21 21

  • a = 7.2030 (2) Å

  • b = 8.3341 (3) Å

  • c = 19.5436 (6) Å

  • V = 1173.21 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.82 mm-1

  • T = 296 K

  • 0.41 × 0.34 × 0.10 mm

Data collection
  • Agilent Xcalibur (Sapphire2) diffractometer

  • Absorption correction: multi-scan (CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]) Tmin = 0.391, Tmax = 0.765

  • 8969 measured reflections

  • 2392 independent reflections

  • 2236 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.026

  • wR(F2) = 0.064

  • S = 1.14

  • 2392 reflections

  • 120 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.89 e Å-3

  • [Delta][rho]min = -0.69 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 986 Friedel pairs

  • Flack parameter: 0.03 (5)

Table 1
Selected bond lengths (Å)

Sn1-Cl1 2.5437 (15)
Sn1-Cl2 2.6489 (11)
Sn1-Cl3 2.5139 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1C...Cl1i 0.89 2.51 3.339 (4) 155
N1-H1C...Cl3ii 0.89 2.85 3.418 (4) 123
N1-H1A...Cl3iii 0.89 2.53 3.329 (4) 151
N1-H1B...Cl2 0.89 2.54 3.371 (6) 157
N1-H1B...Cl1 0.89 2.94 3.515 (4) 124
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x-1, y, z.

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.]); 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: DIAMOND (Brandenburg et al., 1999[Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) 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.]) and 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: VN2066 ).


Acknowledgements

The authors gratefully acknowledge the support of the Tunisian Ministry of Higher Education and Scientific Research and would like to thank I. Ledoux Rak for her support in the second harmonic generation tests.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED. Agilent Technologies, Yarnton, England.
Ben Gozlen, M. H., Kamoun, S., Paulush, H. & Pabst, I. (1994). Z. Kristallogr. 209, 382-382.
Brandenburg, K. & Berndt, M. (1999). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Domenicano, A. & Murray-Rust, P. (1979). Tetrahedron Lett. 20, 2283-2286.  [CrossRef]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Kamoun, S., Daoud, A., Elfakir, A., Quarton, M. & Ledoux, I. (1995). Solid State Commun. 94, 893-897.  [CrossRef] [ChemPort] [ISI]
Karoui, S., Kamoun, S. & Jouini, A. (2013). J. Solid State Chem. 197, 60-68.  [ISI] [CrossRef] [ChemPort]
Kurtz, S. K. & Perry, T. T. (1968). J. Appl. Phys. 39, 798-3813.  [CrossRef] [ISI]
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.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhang, S. J., Lanty, G., Lauret, J. S., Deleporte, E., Audebert, P. & Galmiche, L. (2009). Acta Mater. 57, 3301-3309.  [ISI] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, m187-m188   [ doi:10.1107/S1600536813005096 ]

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