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Volume 69 
Part 1 
Pages o134-o135  
January 2013  

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

Key indicators
Single-crystal X-ray study
T = 297 K
Mean [sigma](C-C) = 0.002 Å
R = 0.047
wR = 0.139
Data-to-parameter ratio = 26.3
Details
Open access

2-Amino-5-methylpyridinium 4-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

The 4-chlorobenzoate anion of the title salt, C6H9N2+·C7H4ClO2-, is nearly planar with a dihedral angle of 5.14 (16)° between the benzene ring and the carboxylate group. In the crystal, the protonated N atom and the 2-amino group of the cation are hydrogen bonded to the carboxylate O atoms of the anion via a pair of N-H...O hydrogen bonds with an R22(8) ring motif. The ion pairs are further connected via N-H...O and weak C-H...O hydrogen bonds, forming a two-dimensional network parallel to the bc plane. The crystal structure also features a [pi]-[pi] stacking interaction between the pyridinium and benzene rings with a centroid-centroid distance of 3.7948 (9) Å.

Related literature

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 4-chlorobenzoic acid, see: Dionysiou et al. (2000[Dionysiou, D. D., Suidan, M. T., Bekou, E., Baudin, I. & Laine, J.-M. (2000). Appl. Catal. B, 26, 153-171.]). For details of hydrogen-bonded supramolecular compounds, see: Aakeroy et al. (2002[Aakeroy, C. B., Beatty, A. M. & Helfrich, B. A. (2002). J. Am. Chem. Soc. 124, 14425-14432.]). For related structures, see: Nahringbauer & Kvick (1977[Nahringbauer, I. & Kvick, Å. (1977). Acta Cryst. B33, 2902-2905.]); Thanigaimani et al. (2012a[Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012a). Acta Cryst. E68, o3195.],b[Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012b). Acta Cryst. E68, o3196-o3197.],c[Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012c). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C6H9N2+·C7H4ClO2-

  • Mr = 264.70

  • Monoclinic, P 21 /c

  • a = 9.8510 (6) Å

  • b = 10.7707 (8) Å

  • c = 12.2123 (7) Å

  • [beta] = 102.335 (2)°

  • V = 1265.84 (14) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.30 mm-1

  • T = 297 K

  • 0.46 × 0.25 × 0.13 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 = 0.876, Tmax = 0.963

  • 17572 measured reflections

  • 4628 independent reflections

  • 2976 reflections with I > 2[sigma](I)

  • Rint = 0.034

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.139

  • S = 1.04

  • 4628 reflections

  • 176 parameters

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

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.31 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H1N2...O1 0.85 (2) 2.02 (2) 2.8654 (18) 174.1 (19)
N1-H1N1...O1i 0.98 (2) 1.75 (2) 2.7255 (14) 174.1 (16)
N2-H2N2...O2i 0.92 (2) 1.83 (2) 2.7437 (17) 172.7 (18)
C2-H2A...O2ii 0.93 2.40 3.1459 (18) 137
Symmetry codes: (i) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]; (ii) -x+1, -y+1, -z+1.

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: IS5231 ).


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., Beatty, A. M. & Helfrich, B. A. (2002). J. Am. Chem. Soc. 124, 14425-14432.  [ISI] [CSD] [CrossRef] [PubMed]
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.
Dionysiou, D. D., Suidan, M. T., Bekou, E., Baudin, I. & Laine, J.-M. (2000). Appl. Catal. B, 26, 153-171.  [ChemPort]
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.
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, o3195.  [CrossRef] [details]
Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012b). Acta Cryst. E68, o3196-o3197.  [CrossRef] [details]
Thanigaimani, K., Farhadikoutenaei, A., Khalib, N. C., Arshad, S. & Razak, I. A. (2012c). Acta Cryst. E68, o3319-o3320.  [CrossRef] [details]


Acta Cryst (2013). E69, o134-o135   [ doi:10.1107/S1600536812051021 ]

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