2-Amino-5-methyl­pyridinium nicotinate

Hemamalini, M.; Fun, H.-K.

doi:10.1107/S1600536810005970

Volume 66
Part 3
Page o662
March 2010

Received 8 February 2010
Accepted 14 February 2010
Online 20 February 2010

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.050
wR = 0.144
Data-to-parameter ratio = 19.8
Details

2-Amino-5-methylpyridinium nicotinate

Madhukar Hemamalini ^a and Hoong-Kun Fun ^a ^*⁺

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
Correspondence e-mail: hkfun@usm.my

In the title compound, C₆H₉N₂⁺·C₆H₄NO₂^-, the 2-amino-5-methylpyridinium cation is essentially planar, with a maximum deviation of 0.023 (2) Å. In the crystal, the cations and anions are linked via strong N-HO hydrogen bonds, forming a two dimensional network parallel to (100). In addition, [pi] [pi] interactions involving the pyridinium and pyridine rings, with centroid-centroid distances of 3.6383 (8) Å, are observed.

Related literature

For background to the chemistry of substituted pyridines, see: Pozharski et al. (1997); Katritzky et al. (1996). For nicotinic acid, see: Athimoolam & Rajaram (2005); Lorenzen et al. (2001); Gielen et al. (1992); Kim et al. (2004). For a related structure, see: Nahringbauer & Kvick (1977). For details of hydrogen bonding, see: Jeffrey & Saenger (1991); Jeffrey (1997); Scheiner (1997). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₆H₉N₂⁺·C₆H₄NO₂^-
M_r = 231.25
Monoclinic, P 2₁ /c
a = 9.4877 (3) Å
b = 11.1403 (3) Å
c = 11.7611 (3) Å
= 110.113 (2)°
V = 1167.29 (6) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.63 × 0.11 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.944, T_max = 0.990
14482 measured reflections
3870 independent reflections
2240 reflections with I > 2(I)
R_int = 0.026

Refinement

R[F² > 2(F²)] = 0.050
wR(F²) = 0.144
S = 1.05
3870 reflections
195 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.20 e Å^-3
_min = -0.20 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O2ⁱ	0.988 (16)	1.703 (16)	2.6899 (15)	176.8 (16)
N2-H1N2O2ⁱⁱ	0.883 (16)	1.999 (16)	2.8756 (17)	171.7 (15)
N2-H2N2O1ⁱ	0.936 (18)	1.878 (18)	2.8122 (17)	176.6 (17)
Symmetry codes: (i) x-1, y, z-1; (ii) $[x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2728 ).

Acknowledgements

MH and HKF thank the Malaysian Government and Universiti Sains Malaysia for the Research University Golden Goose grant No. 1001/PFIZIK/811012. MH thanks Universiti Sains Malaysia for a post-doctoral research 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.
Athimoolam, S. & Rajaram, R. K. (2005). Acta Cryst. E61, o2764-o2767.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bruker (2009). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Gielen, M., Khloufi, A. E., Biesemans, M. & Willem, R. (1992). Polyhedron, 11, 1861-1868.
Jeffrey, G. A. (1997). An Introduction to Hydrogen Bonding. Oxford University Press.
Jeffrey, G. A. & Saenger, W. (1991). Hydrogen Bonding in Biological Structures. Berlin: Springer.
Katritzky, A. R., Rees, C. W. & Scriven, E. F. V. (1996). Comprehensive Heterocyclic Chemistry II. Oxford: Pergamon Press.
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Lorenzen, A., Stannek, C., Lang, H., Andrianov, V., Kalvinsh, I. & Schwabe, U. (2001). Mol. Pharmacol. 59, 349-357.
Nahringbauer, I. & Kvick, Å. (1977). Acta Cryst. B33, 2902-2905.
Pozharski, A. F., Soldatenkov, A. T. & Katritzky, A. R. (1997). Heterocycles in Life and Society. New York: Wiley.
Scheiner, S. (1997). Hydrogen Bonding. A Theoretical Perspective. Oxford University Press.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds