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Volume 69 
Part 1 
Pages o132-o133  
January 2013  

Received 12 December 2012
Accepted 17 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.008 Å
R = 0.073
wR = 0.201
Data-to-parameter ratio = 11.7
Details
Open access

2-Amino-5-methylpyridinium 2-hydroxy-5-chlorobenzoate

aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, and bDepartment of Physics, Faculty of Science, University of Mazandaran, Babolsar, Iran
Correspondence e-mail: arazaki@usm.my

In the 5-chlorosalicylate anion of the title salt, C6H9N2+·C7H4ClO3-, an intramolecular O-H...O hydrogen bond with an S(6) graph-set motif is observed and the dihedral angle between the benzene ring and the -CO2 group is 1.6 (6)°. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxylate O atoms via a pair of N-H...O hydrogen bonds, forming an R22(8) ring motif. The crystal structure also features N-H...O and weak C-H...O interactions, resulting in a layer parallel to (10-1).

Related literature

For details of non-covalent interactions, see: Desiraju (2007[Desiraju, G. R. (2007). Angew. Chem. Int. Ed. 46, 8342-8356.]); Aakeroy & Seddon (1993[Aakeroy, C. B. & Seddon, K. R. (1993). Chem. Soc. Rev. 22, 397-407.]). For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997[Pozharski, A. F., Soldatenkov, A. T. & Katritzky, A. R. (1997). In Heterocycles in Life and Society. New York: Wiley.]); Katritzky et al. (1996[Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). In Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.]). For related structures, see: Nahringbauer & Kvick (1977[Nahringbauer, I. & Kvick, Å. (1977). Acta Cryst. B33, 2902-2905.]); Raza et al. (2010[Raza, A. R., Nisar, B., Tahir, M. N. & Raza, A. (2010). Acta Cryst. E66, o2921.]); Thanigaimani et al. (2012a[Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012a). Acta Cryst. E68, o3196-o3197.],b[Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012b). Acta Cryst. E68, o3319-o3320.]). For hydrogen-bond motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]). For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C6H9N2+·C7H4ClO3-

  • Mr = 280.70

  • Monoclinic, P 21

  • a = 9.004 (7) Å

  • b = 5.767 (5) Å

  • c = 12.617 (10) Å

  • [beta] = 90.415 (16)°

  • V = 655.2 (9) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 100 K

  • 0.46 × 0.18 × 0.07 mm

Data collection
  • Bruker SMART APEXII Duo CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.877, Tmax = 0.979

  • 4785 measured reflections

  • 2204 independent reflections

  • 1539 reflections with I > 2[sigma](I)

  • Rint = 0.061

Refinement
  • R[F2 > 2[sigma](F2)] = 0.073

  • wR(F2) = 0.201

  • S = 1.01

  • 2204 reflections

  • 189 parameters

  • 2 restraints

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

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.44 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 941 Friedel pairs

  • Flack parameter: 0.09 (16)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H1O3...O2 0.92 (6) 1.73 (7) 2.512 (6) 141 (6)
N1-H1N1...O2i 0.94 (6) 1.76 (6) 2.683 (7) 166 (5)
N2-H1N2...O1i 0.85 (5) 1.96 (5) 2.793 (8) 165 (4)
N2-H2N2...O1ii 0.85 (6) 2.04 (7) 2.811 (6) 152 (7)
C8-H8A...O3iii 0.95 2.58 3.425 (7) 148
Symmetry codes: (i) x+1, y+1, z; (ii) [-x+1, y+{\script{1\over 2}}, -z+1]; (iii) [-x+1, y+{\script{1\over 2}}, -z+2].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL 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: IS5232 ).


Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the research facilities and USM Short Term Grant No. 304/PFIZIK/6312078 to conduct this work. KT thanks The Academy of Sciences for the Developing World and USM for a TWAS-USM fellowship.

References

Aakeroy, C. B. & Seddon, K. R. (1993). Chem. Soc. Rev. 22, 397-407.  [CrossRef] [ChemPort] [ISI]
Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.  [CrossRef] [ChemPort] [ISI] [details]
Desiraju, G. R. (2007). Angew. Chem. Int. Ed. 46, 8342-8356.  [ISI] [CrossRef] [ChemPort]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). In Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.
Nahringbauer, I. & Kvick, Å. (1977). Acta Cryst. B33, 2902-2905.  [CrossRef] [details] [ISI]
Pozharski, A. F., Soldatenkov, A. T. & Katritzky, A. R. (1997). In Heterocycles in Life and Society. New York: Wiley.
Raza, A. R., Nisar, B., Tahir, M. N. & Raza, A. (2010). Acta Cryst. E66, o2921.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012a). Acta Cryst. E68, o3196-o3197.  [CrossRef] [details]
Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012b). Acta Cryst. E68, o3319-o3320.  [CrossRef] [details]


Acta Cryst (2013). E69, o132-o133   [ doi:10.1107/S160053681205101X ]

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