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Volume 69 
Part 7 
Pages o1118-o1119  
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) = 0.001 Å
R = 0.036
wR = 0.115
Data-to-parameter ratio = 23.0
Details
Open access

2-Amino-5-methylpyridinium 3-hydroxypyridine-2-carboxylate

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 3-hydroxypicolinate anion of the title salt, C6H9N2+·C6H4NO3-, 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 9.55 (9)° between the pyridine ring and the carboxylate group. In the crystal, the cations and anions are linked via N-H...O hydrogen bonds, forming a centrosymmetric 2 + 2 aggregate with R22(8) and R42(8) ring motifs. The crystal structure also features N-H...N and weak C-H...[pi] interactions.

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 related structures, see: Nahringbauer & Kvick (1977[Nahringbauer, I. & Kvick, Å. (1977). Acta Cryst. B33, 2902-2905.]); Robert et al. (2001[Robert, J. J., Raj, S. B. & Muthiah, P. T. (2001). Acta Cryst. E57, o1206-o1208.]); Thanigaimani et al. (2010[Thanigaimani, K., Devi, P., Muthiah, P. T., Lynch, D. E. & Butcher, R. J. (2010). Acta Cryst. C66, o324-o328.], 2013[Thanigaimani, K., Khalib, N. C., Arshad, S. & Razak, I. A. (2013). Acta Cryst. E69, o318.]). 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 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+·C6H4NO3-

  • Mr = 247.25

  • Monoclinic, P 21 /c

  • a = 7.3443 (4) Å

  • b = 16.4321 (9) Å

  • c = 10.8235 (5) Å

  • [beta] = 118.250 (3)°

  • V = 1150.62 (10) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 100 K

  • 0.58 × 0.29 × 0.16 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 = 0.942, Tmax = 0.984

  • 15996 measured reflections

  • 4132 independent reflections

  • 3596 reflections with I > 2[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.036

  • wR(F2) = 0.115

  • S = 1.04

  • 4132 reflections

  • 180 parameters

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

  • [Delta][rho]max = 0.47 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C1-C5 ring.

D-H...A D-H H...A D...A D-H...A
O1-H1O1...O2 0.93 (2) 1.66 (2) 2.5239 (10) 152 (2)
N3-H2N3...O3i 0.885 (15) 1.969 (15) 2.8504 (11) 174.0 (14)
N3-H1N3...O3ii 0.859 (14) 2.248 (15) 2.8093 (10) 123.0 (12)
N3-H1N3...N1ii 0.859 (14) 2.416 (14) 3.2481 (10) 163.2 (13)
N2-H1N2...O2i 0.943 (16) 1.796 (16) 2.7327 (10) 171.4 (13)
C9-H9A...Cg1 0.95 2.59 3.4702 (10) 154
C11-H11A...Cg1iii 0.95 2.71 3.3956 (8) 130
Symmetry codes: (i) [-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (ii) [x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]; (iii) [-x, y-{\script{1\over 2}}, -z+{\script{1\over 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: IS5281 ).


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

Aakeroy, C. B. & Seddon, K. R. (1993). Chem. Soc. Rev. 22, 397-407.  [CrossRef] [ChemPort] [Web of Science]
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]
Desiraju, G. R. (2007). Angew. Chem. Int. Ed. 46, 8342-8356.  [Web of Science] [CrossRef] [ChemPort]
Nahringbauer, I. & Kvick, Å. (1977). Acta Cryst. B33, 2902-2905.  [CrossRef] [IUCr Journals] [Web of Science]
Robert, J. J., Raj, S. B. & Muthiah, P. T. (2001). Acta Cryst. E57, o1206-o1208.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
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]
Thanigaimani, K., Devi, P., Muthiah, P. T., Lynch, D. E. & Butcher, R. J. (2010). Acta Cryst. C66, o324-o328.  [CSD] [CrossRef] [ChemPort] [IUCr Journals]
Thanigaimani, K., Khalib, N. C., Arshad, S. & Razak, I. A. (2013). Acta Cryst. E69, o318.  [CrossRef] [IUCr Journals]


Acta Cryst (2013). E69, o1118-o1119   [ doi:10.1107/S1600536813016322 ]

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