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Volume 69 
Part 9 
Page o1453  
September 2013  

Received 13 August 2013
Accepted 13 August 2013
Online 21 August 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.071
wR = 0.216
Data-to-parameter ratio = 36.3
Details
Open access

4-Methylbenzylammonium nitrate

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

In the title salt, C8H12N+·NO3-, the N atom of the 4-methylbenzylammonium cation is displaced by 1.366 (2) Å from the mean plane of the other atoms. In the crystal, the cations are connected to the anions by N-H...O and N-H...(O,O) hydrogen bonds, generating a layered network parallel to (100). A weak C-H...O interaction also occurs.

Related literature

For related structures, see: Kefi et al. (2011[Kefi, R., Jeanneau, E., Lefebvre, F. & Ben Nasr, C. (2011). Acta Cryst. C67, m126-m129.]); Rahmouni et al. (2011[Rahmouni, H., Smirani Sta, W., Al-Deyab, S. S. & Rzaigui, M. (2011). Acta Cryst. E67, o2334.]). For a discussion on hydrogen bonding, see: Brown (1976[Brown, I. D. (1976). Acta Cryst. A32, 24-31.]); Blessing (1986[Blessing, R. H. (1986). Acta Cryst. B42, 613-621.]). For aromatic [pi]-[pi] stacking interactions, see: Janiak (2000[Janiak, J. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.]). For graph-set notation of hydrogen-bonding patterns, 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

  • Monoclinic, P 21 /c

  • a = 15.097 (2) Å

  • b = 5.8121 (10) Å

  • c = 10.486 (2) Å

  • [beta] = 99.75 (2)°

  • V = 906.8 (3) Å3

  • Z = 4

  • Ag K[alpha] radiation

  • [lambda] = 0.56083 Å

  • [mu] = 0.06 mm-1

  • T = 293 K

  • 0.40 × 0.35 × 0.30 mm

Data collection
  • Enraf-Nonius CAD-4 diffractometer

  • 6579 measured reflections

  • 4430 independent reflections

  • 2415 reflections with I > 2[sigma](I)

  • Rint = 0.033

  • 2 standard reflections every 120 min intensity decay: 1%

Refinement
  • R[F2 > 2[sigma](F2)] = 0.071

  • wR(F2) = 0.216

  • S = 0.96

  • 4430 reflections

  • 122 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.31 e Å-3

  • [Delta][rho]min = -0.17 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1A...O1i 0.89 2.07 2.936 (3) 164
N1-H1A...O3i 0.89 2.52 3.065 (2) 120
N1-H1B...O3ii 0.89 2.12 2.9378 (19) 153
N1-H1C...O3 0.89 2.01 2.900 (2) 179
N1-H1C...O2 0.89 2.55 3.158 (3) 126
C8-H8A...O1iii 0.97 2.45 3.234 (2) 138
Symmetry codes: (i) x, y+1, z; (ii) -x+1, -y+2, -z+1; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

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: HB7131 ).


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]
Blessing, R. H. (1986). Acta Cryst. B42, 613-621.  [CSD] [CrossRef] [ISI] [details]
Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal impact GbR, Bonn, Germany.
Brown, I. D. (1976). Acta Cryst. A32, 24-31.  [CrossRef] [details]
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.
Janiak, J. (2000). J. Chem. Soc. Dalton Trans. pp. 3885-3896.  [CrossRef]
Kefi, R., Jeanneau, E., Lefebvre, F. & Ben Nasr, C. (2011). Acta Cryst. C67, m126-m129.  [CSD] [CrossRef] [ChemPort] [details]
Rahmouni, H., Smirani Sta, W., Al-Deyab, S. S. & Rzaigui, M. (2011). Acta Cryst. E67, o2334.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o1453  [ doi:10.1107/S1600536813022836 ]

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