Anilinium-3-carboxyl­ate 3-carb­oxy­anilinium nitrate

Ahmad, S.; Hussain, S.; Sharif, S.; Khan, I.U.; Tahir, M.N.

doi:10.1107/S1600536812049392

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 (C-C) = 0.002 Å
R = 0.037
wR = 0.101
Data-to-parameter ratio = 14.0
Details

Anilinium-3-carboxylate 3-carboxyanilinium nitrate

Saeed Ahmad,^a ^* Sajjad Hussain,^b Shahzad Sharif,^b Islam Ullah Khan ^b and Muhammad Nawaz Tahir ^c

^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-HO hydrogen bond, in the crystal, the various units are linked via N-HO and C-HO hydrogen bonds forming a three-dimensional structure.

Related literature

For applications of aminobenzoic acids, see: Congiu et al. (2005); Swislocka et al. (2005). For related structures and details of their hydrogen-bonding motifs, see: Arora et al. (1973); Bahadur et al. (2007); Hansen et al. (2007); Lai & Marsh (1967); Lu et al. (2001); Smith et al. (1995); Zaidi et al. (2008).

Experimental

Crystal data

C₇H₈NO₂⁺·NO₃^-·C₇H₇NO₂
M_r = 337.29
Monoclinic, C 2/c
a = 16.0451 (3) Å
b = 4.7575 (1) Å
c = 19.7143 (4) Å
= 107.660 (1)°
V = 1433.96 (5) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.525, T_max = 0.806
6955 measured reflections
1777 independent reflections
1604 reflections with I > 2(I)
R_int = 0.017

Refinement

R[F² > 2(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
_max = 0.29 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O1-H1OO1ⁱ	0.88 (4)	1.61 (4)	2.4868 (13)	171 (4)
O1-H1OO2ⁱ	0.88 (4)	2.55 (3)	3.0686 (14)	118 (3)
N1-H1NO2ⁱⁱ	0.913 (18)	2.027 (19)	2.9157 (13)	164.2 (17)
N1-H2NO2ⁱⁱⁱ	0.944 (18)	1.918 (18)	2.8609 (13)	177.0 (16)
N1-H3NO3^iv	0.939 (19)	2.498 (15)	2.9220 (14)	107.6 (11)
N1-H3NO3	0.939 (19)	2.526 (15)	2.9582 (14)	108.3 (11)
N1-H3NO4	0.939 (19)	1.920 (19)	2.8345 (11)	163.9 (13)
C3-H3O2ⁱⁱ	0.93	2.41	3.1189 (15)	132
C5-H5O3^iv	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); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97, PLATON and publCIF (Westrip, 2010).

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.
Bahadur, S. A., Kannan, R. S. & Sridhar, B. (2007). Acta Cryst. E63, o2722-o2723.
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.
Hansen, L. K., Perlovich, G. L. & Bauer-Brandl, A. (2007). Acta Cryst. E63, o2361.
Lai, T. F. & Marsh, R. E. (1967). Acta Cryst. 22, 885-893.
Lu, T. H., Chattopadhyay, P., Liao, F. L. & Lo, J.-M. (2001). Anal. Sci. 17, 905-906.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Smith, G., Lynch, D. E., Byriel, K. A. & Kennard, C. H. L. (1995). Aust. J. Chem. 48, 1133-1149.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Swislocka, R., Regulska, E., Samsonowicz, M., Hrynaszkiewicz, T. & Lewandowski, W. (2005). Spectrochim. Acta Part A, 61, 2966-2973.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.
Zaidi, S. A. R. A., Tahir, M. N., Iqbal, J. & Chaudhary, M. A. (2008). Acta Cryst. E64, o1957.

organic compounds