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Volume 69 
Part 9 
Page o1475  
September 2013  

Received 18 August 2013
Accepted 20 August 2013
Online 23 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.060
wR = 0.178
Data-to-parameter ratio = 37.5
Details
Open access

2,3-Xylidinium nitrate

aLaboratoire de chimie des Matériaux, Faculté des Sciences de Bizerte, 7021 Zarzouna Bizerte, Tunisia
Correspondence e-mail: houda_marouani@voila.fr

In the crystal structure of the title compound, C8H12N+·NO3-, the 2,3-xylidinium (2,3-dimethylanilinium) cations are connected to the nitrate anions through bifurcated N-H...(O,O) and weak C-H...O hydrogen bonds, generating corrugated layers parallel to (001) at z = 0.25 and 0.75. These layers are connected via C-H...O interactions, giving rise to a three-dimensional network.

Related literature

For related structures, see: Marouani et al. (2010[Marouani, H., Elmi, L., Rzaigui, M. & Al-Deyab, S. S. (2010). Acta Cryst. E66, o535.], 2012[Marouani, H., Raouafi, N., Toumi Akriche, S., Al-Deyab, S. S. & Rzaigui, M. (2012). E-J. Chem. 9, 772-779.]). For graph-set notation of hydrogen-bonding motifs, see: Bernstein et al. (1995[Bernstein, J., David, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C8H12N+·NO3-

  • Mr = 184.20

  • Orthorhombic, P b c a

  • a = 10.889 (2) Å

  • b = 10.110 (2) Å

  • c = 17.010 (3) Å

  • V = 1872.5 (6) Å3

  • Z = 8

  • Ag K[alpha] radiation

  • [lambda] = 0.56083 Å

  • [mu] = 0.06 mm-1

  • T = 293 K

  • 0.4 × 0.3 × 0.2 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 8719 measured reflections

  • 4541 independent reflections

  • 1933 reflections with I > 2[sigma](I)

  • Rint = 0.056

  • 2 standard reflections every 120 min intensity decay: 2%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.178

  • S = 0.86

  • 4541 reflections

  • 121 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.13 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2A...O3 0.89 2.03 2.915 (2) 177
N2-H2A...O2 0.89 2.64 3.296 (2) 131
N2-H2B...O1i 0.89 2.11 2.995 (2) 171
N2-H2B...O2i 0.89 2.46 3.148 (2) 134
N2-H2C...O3ii 0.89 2.15 2.973 (2) 153
N2-H2C...O1ii 0.89 2.36 3.158 (2) 149
C4-H4...O2iii 0.93 2.57 3.439 (3) 156
C7-H7A...O1ii 0.96 2.63 3.522 (3) 155
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]; (iii) -x, -y+1, -z+1.

Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994[Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Putz 2005[Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal impact GbR, Bonn, Germany.]); 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: PV2645 ).


Acknowledgements

This work was supported by the Tunisian Ministry of HEScR.

References

Bernstein, J., David, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal impact GbR, Bonn, Germany.
Enraf-Nonius (1994). CAD-4 EXPRESS. Enraf-Nonius, Delft, The Netherlands.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
Marouani, H., Elmi, L., Rzaigui, M. & Al-Deyab, S. S. (2010). Acta Cryst. E66, o535.  [CSD] [CrossRef] [details]
Marouani, H., Raouafi, N., Toumi Akriche, S., Al-Deyab, S. S. & Rzaigui, M. (2012). E-J. Chem. 9, 772-779.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1475  [ doi:10.1107/S1600536813023465 ]

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