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Volume 69 
Part 6 
Page o910  
June 2013  

Received 18 April 2013
Accepted 11 May 2013
Online 18 May 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.041
wR = 0.125
Data-to-parameter ratio = 16.9
Details
Open access

2-Amino-4-methylpyridinium 2-nitrobenzoate

aDepartment of Physics, Anna University, Chennai 600 025, India, and bCentre of Advanced Study in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai 600 025, India
Correspondence e-mail: shirai2011@gmail.com

In the title molecular salt, C6H9N2+·C7H4NO4-, the original pyridine N atom of 2-amino-4-methylpyridine is protonated and the carboxylic acid group of nitrobenzoic acid is deprotonated. In the crystal, the ions are linked by N-H...O hydrogen bonds, forming chains propagating along [001]. The chains are linked via C-H...O hydrogen bonds, forming two-dimensional networks lying parallel to the bc plane.

Related literature

For related structures, see: Navarro Ranninger et al. (1985[Navarro Ranninger, M.-C., Martínez-Carrera, S. & García-Blanco, S. (1985). Acta Cryst. C41, 21-22.]); Luque et al. (1997[Luque, A., Sertucha, J., Lezama, L., Rojo, T. & Roman, P. (1997). J. Chem. Soc. Dalton Trans. pp. 847-854.]); Qin et al. (1999[Qin, J. G., Su, N. B., Dai, C. Y., Yang, C. L., Liu, D. Y., Day, M. W., Wu, B. C. & Chen, C. T. (1999). Polyhedron, 18, 3461-3464.]); Jin et al. (2001[Jin, Z. M., Pan, Y. J., Hu, M. L. & Shen, L. (2001). J. Chem. Crystallogr. 31, 191-195.]); Albrecht et al. (2003[Albrecht, A. S., Landee, C. P. & Turnbull, M. M. (2003). J. Chem. Crystallogr. 33, 269-276.]); Kvick & Noordik (1977[Kvick, Å. & Noordik, J. (1977). Acta Cryst. B33, 2862-2866.]).

[Scheme 1]

Experimental

Crystal data
  • C6H9N2+·C7H4NO4-

  • Mr = 275.26

  • Monoclinic, P 21 /c

  • a = 12.2049 (3) Å

  • b = 9.8463 (2) Å

  • c = 11.5405 (2) Å

  • [beta] = 107.106 (1)°

  • V = 1325.51 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.30 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.969, Tmax = 0.979

  • 12523 measured reflections

  • 3289 independent reflections

  • 2644 reflections with I > 2[sigma](I)

  • Rint = 0.023

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.125

  • S = 1.06

  • 3289 reflections

  • 195 parameters

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

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N3-H3A...O4i 0.933 (18) 1.752 (19) 2.6746 (16) 169.5 (17)
N4-H4A...O3i 0.923 (19) 1.972 (19) 2.8734 (18) 164.9 (17)
N4-H4B...O4ii 0.871 (19) 2.033 (19) 2.8937 (16) 169.7 (18)
C11-H11...O3iii 0.93 2.58 3.3624 (16) 142
Symmetry codes: (i) -x+2, -y, -z+1; (ii) [-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]; (iii) [x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SU2590 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection. TS and DV thank the UGC (SAP-CAS) for the departmental facilties. TS also thanks DST Inspire for financial assistance.

References

Albrecht, A. S., Landee, C. P. & Turnbull, M. M. (2003). J. Chem. Crystallogr. 33, 269-276.  [ISI] [CSD] [CrossRef] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jin, Z. M., Pan, Y. J., Hu, M. L. & Shen, L. (2001). J. Chem. Crystallogr. 31, 191-195.  [ISI] [CSD] [CrossRef] [ChemPort]
Kvick, Å. & Noordik, J. (1977). Acta Cryst. B33, 2862-2866.  [CrossRef] [details] [ISI]
Luque, A., Sertucha, J., Lezama, L., Rojo, T. & Roman, P. (1997). J. Chem. Soc. Dalton Trans. pp. 847-854.  [CrossRef]
Navarro Ranninger, M.-C., Martínez-Carrera, S. & García-Blanco, S. (1985). Acta Cryst. C41, 21-22.  [CrossRef] [details]
Qin, J. G., Su, N. B., Dai, C. Y., Yang, C. L., Liu, D. Y., Day, M. W., Wu, B. C. & Chen, C. T. (1999). Polyhedron, 18, 3461-3464.  [ISI] [CSD] [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o910  [ doi:10.1107/S1600536813012919 ]

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