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Volume 69 
Part 1 
Page o29  
January 2013  

Received 1 November 2012
Accepted 1 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.037
wR = 0.101
Data-to-parameter ratio = 14.0
Details
Open access

Anilinium-3-carboxylate 3-carboxyanilinium nitrate

aDepartment of Chemistry, University of Engineering and Technology, Lahore 54890, Pakistan,bDepartment of Chemistry, Government College University, Lahore, Pakistan, and cDepartment of Physics, University of Sargodha, Sagrodha, Pakistan
Correspondence e-mail: saeed_a786@hotmail.com

The title compound, C7H8NO2+·NO3-·C7H7NO2, exists in the form of a protonated dimer of two anilinium-3-carboxylate molecules related by an inversion center, and a nitrate anion located on a twofold rotation axis. The bridging H atom occupies, with equal probability, the two sites associated with the carboxyl atoms. In addition to the strong O-H...O hydrogen bond, in the crystal, the various units are linked via N-H...O and C-H...O hydrogen bonds forming a three-dimensional structure.

Related literature

For applications of aminobenzoic acids, see: Congiu et al. (2005[Congiu, C., Cocco, M. T., Lilliu, V. & Onnis, V. (2005). J. Med. Chem. 48, 8245-8252.]); Swislocka et al. (2005[Swislocka, R., Regulska, E., Samsonowicz, M., Hrynaszkiewicz, T. & Lewandowski, W. (2005). Spectrochim. Acta Part A, 61, 2966-2973.]). For related structures and details of their hydrogen-bonding motifs, see: Arora et al. (1973[Arora, S. K., Sundaralingam, M., Dancz, J. S., Stanford, R. H. & Marsh, R. E. (1973). Acta Cryst. B29, 1849-1855.]); Bahadur et al. (2007[Bahadur, S. A., Kannan, R. S. & Sridhar, B. (2007). Acta Cryst. E63, o2722-o2723.]); Hansen et al. (2007[Hansen, L. K., Perlovich, G. L. & Bauer-Brandl, A. (2007). Acta Cryst. E63, o2361.]); Lai & Marsh (1967[Lai, T. F. & Marsh, R. E. (1967). Acta Cryst. 22, 885-893.]); Lu et al. (2001[Lu, T. H., Chattopadhyay, P., Liao, F. L. & Lo, J.-M. (2001). Anal. Sci. 17, 905-906.]); Smith et al. (1995[Smith, G., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1995). Aust. J. Chem. 48, 1133-1149.]); Zaidi et al. (2008[Zaidi, S. A. R. A., Tahir, M. N., Iqbal, J. & Chaudhary, M. A. (2008). Acta Cryst. E64, o1957.]).

[Scheme 1]

Experimental

Crystal data
  • C7H8NO2+·NO3-·C7H7NO2

  • Mr = 337.29

  • Monoclinic, C 2/c

  • a = 16.0451 (3) Å

  • b = 4.7575 (1) Å

  • c = 19.7143 (4) Å

  • [beta] = 107.660 (1)°

  • V = 1433.96 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 296 K

  • 0.23 × 0.16 × 0.07 mm

Data collection
  • Bruker Kappa APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.525, Tmax = 0.806

  • 6955 measured reflections

  • 1777 independent reflections

  • 1604 reflections with I > 2[sigma](I)

  • Rint = 0.017

Refinement
  • R[F2 > 2[sigma](F2)] = 0.037

  • wR(F2) = 0.101

  • S = 1.07

  • 1777 reflections

  • 127 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.29 e Å-3

  • [Delta][rho]min = -0.20 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O...O1i 0.88 (4) 1.61 (4) 2.4868 (13) 171 (4)
O1-H1O...O2i 0.88 (4) 2.55 (3) 3.0686 (14) 118 (3)
N1-H1N...O2ii 0.913 (18) 2.027 (19) 2.9157 (13) 164.2 (17)
N1-H2N...O2iii 0.944 (18) 1.918 (18) 2.8609 (13) 177.0 (16)
N1-H3N...O3iv 0.939 (19) 2.498 (15) 2.9220 (14) 107.6 (11)
N1-H3N...O3 0.939 (19) 2.526 (15) 2.9582 (14) 108.3 (11)
N1-H3N...O4 0.939 (19) 1.920 (19) 2.8345 (11) 163.9 (13)
C3-H3...O2ii 0.93 2.41 3.1189 (15) 132
C5-H5...O3iv 0.93 2.58 3.3058 (18) 135
Symmetry codes: (i) -x, -y+2, -z; (ii) [-x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]; (iii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (iv) x, y-1, z.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: SHELXL97, PLATON 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: KJ2215 ).


Acknowledgements

The authors are grateful to Government College University Lahore for providing the X-ray diffraction facility, and to Professor Helen Stoeckli-Evans for valuable discussions.

References

Arora, S. K., Sundaralingam, M., Dancz, J. S., Stanford, R. H. & Marsh, R. E. (1973). Acta Cryst. B29, 1849-1855.  [CrossRef] [ChemPort] [details] [ISI]
Bahadur, S. A., Kannan, R. S. & Sridhar, B. (2007). Acta Cryst. E63, o2722-o2723.  [CSD] [CrossRef] [details]
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Congiu, C., Cocco, M. T., Lilliu, V. & Onnis, V. (2005). J. Med. Chem. 48, 8245-8252.  [ISI] [CrossRef] [PubMed] [ChemPort]
Hansen, L. K., Perlovich, G. L. & Bauer-Brandl, A. (2007). Acta Cryst. E63, o2361.  [CSD] [CrossRef] [details]
Lai, T. F. & Marsh, R. E. (1967). Acta Cryst. 22, 885-893.  [CrossRef] [ChemPort] [details]
Lu, T. H., Chattopadhyay, P., Liao, F. L. & Lo, J.-M. (2001). Anal. Sci. 17, 905-906.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Smith, G., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1995). Aust. J. Chem. 48, 1133-1149.  [CrossRef] [ChemPort] [ISI]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Swislocka, R., Regulska, E., Samsonowicz, M., Hrynaszkiewicz, T. & Lewandowski, W. (2005). Spectrochim. Acta Part A, 61, 2966-2973.  [ChemPort]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zaidi, S. A. R. A., Tahir, M. N., Iqbal, J. & Chaudhary, M. A. (2008). Acta Cryst. E64, o1957.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o29  [ doi:10.1107/S1600536812049392 ]

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