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Volume 69 
Part 7 
Page o1120  
July 2013  

Received 6 June 2013
Accepted 12 June 2013
Online 19 June 2013

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.002 Å
R = 0.060
wR = 0.130
Data-to-parameter ratio = 20.6
Details
Open access

2-Amino-4-methylpyridinium 3-hydroxybenzoate

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

In the title salt, C6H9N2+·C7H5O3-, the anion is essentially planar, with a dihedral angle of 2.72 (17)° between the benzene ring and the carboxylate group. In the crystal, the anions are connected by O-H...O hydrogen bonds, forming a 41 helical chain along the c axis. 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 another N-H...O hydrogen bond, resulting in a three-dimensional network.

Related literature

For the role of hydrogen bonding in crystal engineering, see: Goswami & Ghosh (1997[Goswami, S. & Ghosh, K. (1997). Tetrahedron Lett. 38, 4503-4506.]); Goswami et al. (1998[Goswami, S., Mahapatra, A. K., Nigam, G. D., Chinnakali, K. & Fun, H.-K. (1998). Acta Cryst. C54, 1301-1302.]); Lehn (1992[Lehn, J. M. (1992). J. Coord. Chem. 27, 3-6.]). For related structures, see: Kvick & Noordik (1977[Kvick, Å. & Noordik, J. (1977). Acta Cryst. B33, 2862-2866.]). 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 in 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+·C7H5O3-

  • Mr = 246.26

  • Tetragonal, I 41 /a

  • a = 15.4435 (2) Å

  • c = 21.0395 (3) Å

  • V = 5017.96 (12) Å3

  • Z = 16

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 100 K

  • 0.43 × 0.26 × 0.23 mm

Data collection
  • Bruker SMART APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.961, Tmax = 0.979

  • 46924 measured reflections

  • 3702 independent reflections

  • 3092 reflections with I > 2[sigma](I)

  • Rint = 0.058

Refinement
  • R[F2 > 2[sigma](F2)] = 0.060

  • wR(F2) = 0.130

  • S = 1.10

  • 3702 reflections

  • 180 parameters

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

  • [Delta][rho]max = 0.45 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1O1...O2i 0.89 (2) 1.81 (2) 2.6970 (15) 172 (2)
N1-H1N1...O2ii 0.92 (2) 1.81 (2) 2.7221 (15) 172 (2)
N2-H1N2...O3ii 0.88 (2) 1.91 (2) 2.7852 (16) 170.6 (19)
N2-H2N2...O3 0.883 (19) 1.994 (19) 2.8454 (17) 161.7 (18)
Symmetry codes: (i) [-y+{\script{5\over 4}}, x-{\script{1\over 4}}, z-{\script{1\over 4}}]; (ii) [y+{\script{1\over 4}}, -x+{\script{7\over 4}}, -z+{\script{7\over 4}}].

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: IS5282 ).


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 the 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] [Web of Science]
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] [Web of Science] [IUCr Journals]
Goswami, S. & Ghosh, K. (1997). Tetrahedron Lett. 38, 4503-4506.  [CrossRef] [ChemPort] [Web of Science]
Goswami, S., Mahapatra, A. K., Nigam, G. D., Chinnakali, K. & Fun, H.-K. (1998). Acta Cryst. C54, 1301-1302.  [CSD] [CrossRef] [IUCr Journals]
Kvick, Å. & Noordik, J. (1977). Acta Cryst. B33, 2862-2866.  [CrossRef] [IUCr Journals] [Web of Science]
Lehn, J. M. (1992). J. Coord. Chem. 27, 3-6.  [CrossRef] [Web of Science]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1120  [ doi:10.1107/S1600536813016310 ]

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