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Volume 68 
Part 11 
Pages o3151-o3152  
November 2012  

Received 19 September 2012
Accepted 2 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean [sigma](C-C) = 0.001 Å
R = 0.039
wR = 0.116
Data-to-parameter ratio = 24.6
Details
Open access

2-Amino-5-methylpyridinium 6-oxo-1,6-dihydropyridine-2-carboxylate

The anion of the title salt, C6H9N2+·C6H4NO3-, undergoes an enol-to-keto tautomerism during the crystallization. In the crystal structure, the cation and anion are held together by a relatively short N-H...O hydrogen bond, and the two anions are further connected to each other by a pair of N-H...O hydrogen bonds with an R22(8) ring motif, thus forming a centrosymmetric 2 + 2 aggregate. The aggregates are further linked through weak N-H...O and C-H...O hydrogen bonds, resulting a three-dimensional network.

Related literature

For details of 2-aminopyridine and its derivatives, see: Banerjee & Murugavel (2004[Banerjee, S. & Murugavel, R. (2004). Cryst. Growth Des. 4, 545-552.]); Bis & Zaworotko (2005[Bis, J. A. & Zaworotko, M. J. (2005). Cryst. Growth Des. 5, 1169-1179.]); Bis et al. (2006[Bis, J. A., McLaughlin, O. L., Vishweshwar, P. & Zaworoto, M. J. (2006). Cryst. Growth Des. 6, 2648-2650.]). For details of 6-hydroxypicolinic acid, see: Sun et al. (2004[Sun, C. Y., Zheng, X. J. & Jin, L. P. (2004). Z. Anorg. Allg. Chem. 630, 1342-1347.]); Soares-Santos et al. (2003[Soares-Santos, P. C. R., Nogueira, H. I. S., Rocha, J., Felix, V., Drew, M. G. B., Sa Ferreira, R. A., Carlos, L. D. & Trindade, T. (2003). Polyhedron, 22, 3529-3539.]). For a related structure, see: Sawada & Ohashi (1998[Sawada, K. & Ohashi, Y. (1998). Acta Cryst. C54, 1491-1493.]). 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 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+·C6H4NO3-

  • Mr = 247.25

  • Monoclinic, P 21 /c

  • a = 11.7093 (6) Å

  • b = 10.4594 (6) Å

  • c = 11.4590 (6) Å

  • [beta] = 119.203 (1)°

  • V = 1225.03 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.10 mm-1

  • T = 100 K

  • 0.45 × 0.35 × 0.23 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 = 0.957, Tmax = 0.978

  • 15984 measured reflections

  • 4430 independent reflections

  • 3745 reflections with I > 2[sigma](I)

  • Rint = 0.027

Refinement
  • R[F2 > 2[sigma](F2)] = 0.039

  • wR(F2) = 0.116

  • S = 1.02

  • 4430 reflections

  • 180 parameters

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

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1N1...O1i 0.899 (15) 2.011 (15) 2.8922 (10) 166.0 (16)
N3-H2N3...O1 0.900 (16) 2.245 (19) 3.0373 (12) 146.7 (15)
N3-H2N3...O3i 0.900 (16) 2.408 (16) 3.0916 (11) 133.0 (15)
N3-H1N3...O2ii 0.938 (15) 1.884 (16) 2.8071 (12) 167.7 (15)
N2-H1N2...O3i 0.954 (16) 1.686 (18) 2.6206 (11) 165.7 (17)
C3-H3A...O1iii 0.95 2.33 3.2598 (11) 166
C9-H9A...O1iv 0.95 2.54 3.3750 (12) 146
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) [-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (iv) [-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: IS5197 ).


Acknowledgements

The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for research facilities and the Fundamental Research Grant Scheme (FRGS) No. 203/PFIZIK/6711171 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.
Banerjee, S. & Murugavel, R. (2004). Cryst. Growth Des. 4, 545-552.  [CSD] [CrossRef] [ChemPort]
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.  [CrossRef] [ChemPort] [ISI]
Bis, J. A., McLaughlin, O. L., Vishweshwar, P. & Zaworoto, M. J. (2006). Cryst. Growth Des. 6, 2648-2650.  [CSD] [CrossRef] [ChemPort]
Bis, J. A. & Zaworotko, M. J. (2005). Cryst. Growth Des. 5, 1169-1179.  [CSD] [CrossRef] [ChemPort]
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]
Sawada, K. & Ohashi, Y. (1998). Acta Cryst. C54, 1491-1493.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Soares-Santos, P. C. R., Nogueira, H. I. S., Rocha, J., Felix, V., Drew, M. G. B., Sa Ferreira, R. A., Carlos, L. D. & Trindade, T. (2003). Polyhedron, 22, 3529-3539.  [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Sun, C. Y., Zheng, X. J. & Jin, L. P. (2004). Z. Anorg. Allg. Chem. 630, 1342-1347.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2012). E68, o3151-o3152   [ doi:10.1107/S1600536812041359 ]

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