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Volume 69 
Part 4 
Pages o537-o538  
April 2013  

Received 27 February 2013
Accepted 8 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.005 Å
R = 0.046
wR = 0.091
Data-to-parameter ratio = 22.5
Details
Open access

2-Amino-5-bromopyridinium 5-chloro-2-hydroxybenzoate

aSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: arazaki@usm.my

In the 5-chlorosalicylate anion of the title salt, C5H6BrN2+·C7H4ClO3-, an intramolecular O-H...O hydrogen bond with an S(6) graph-set motif is formed, so that the anion is essentially planar with a dihedral angle of 1.3 (5)° 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 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 the (10-1) plane.

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 related structures, see: Goubitz et al. (2001[Goubitz, K., Sonneveld, E. J. & Schenk, H. (2001). Z. Kristallogr. 216, 176-181.]); Quah et al. (2010[Quah, C. K., Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o2164-o2165.]); Thanigaimani et al. (2013[Thanigaimani, K., Farhadikoutenaei, A., Arshad, S. & Razak, I. A. (2013). Acta Cryst. E69, o132-o133.]); Raza et al. (2010[Raza, A. R., Nisar, B., Tahir, M. N. & Raza, A. (2010). Acta Cryst. E66, o2921.]). 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 stability of the temperature controller used for data collection, see: Cosier & Glazer (1986[Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.]).

[Scheme 1]

Experimental

Crystal data
  • C5H6BrN2+·C7H4ClO3-

  • Mr = 345.58

  • Monoclinic, P 21

  • a = 8.9769 (17) Å

  • b = 5.6601 (12) Å

  • c = 12.753 (2) Å

  • [beta] = 90.662 (5)°

  • V = 647.9 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 3.38 mm-1

  • T = 100 K

  • 0.31 × 0.04 × 0.03 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 = 0.417, Tmax = 0.894

  • 8030 measured reflections

  • 4233 independent reflections

  • 3014 reflections with I > 2[sigma](I)

  • Rint = 0.087

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.091

  • S = 0.91

  • 4233 reflections

  • 188 parameters

  • 1 restraint

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

  • [Delta][rho]max = 0.84 e Å-3

  • [Delta][rho]min = -0.98 e Å-3

  • Absolute structure: Flack (1983[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1558 Friedel pairs

  • Flack parameter: 0.037 (11)

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H1O3...O2 0.77 (8) 2.02 (5) 2.553 (4) 127 (6)
N1-H1N1...O2i 0.86 (5) 1.82 (5) 2.666 (4) 172 (4)
N2-H1N2...O1i 0.96 (6) 1.81 (6) 2.770 (5) 175 (4)
N2-H2N2...O1ii 0.88 (5) 1.95 (5) 2.799 (5) 164 (3)
C8-H8A...O3iii 0.95 2.53 3.410 (5) 154
Symmetry codes: (i) [-x+2, y-{\script{3\over 2}}, -z+1]; (ii) x, y-1, z-1; (iii) [-x+1, y-{\script{1\over 2}}, -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: IS5251 ).


Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for research facilities and a 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

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]
Flack, H. D. (1983). Acta Cryst. A39, 876-881.  [CrossRef] [details]
Goubitz, K., Sonneveld, E. J. & Schenk, H. (2001). Z. Kristallogr. 216, 176-181.  [CrossRef] [ChemPort]
Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). In Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.
Pozharski, A. F., Soldatenkov, A. T. & Katritzky, A. R. (1997). In Heterocycles in Life and Society. New York: Wiley.
Quah, C. K., Hemamalini, M. & Fun, H.-K. (2010). Acta Cryst. E66, o2164-o2165.  [CSD] [CrossRef] [details]
Raza, A. R., Nisar, B., Tahir, M. N. & Raza, A. (2010). Acta Cryst. E66, o2921.  [CSD] [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., Arshad, S. & Razak, I. A. (2013). Acta Cryst. E69, o132-o133.  [CSD] [CrossRef] [details]


Acta Cryst (2013). E69, o537-o538   [ doi:10.1107/S160053681300665X ]

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