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

Thanigaimani, K.; Farhadikoutenaei, A.; Khalib, N.C.; Arshad, S.; Razak, I.A.

doi:10.1107/S1600536812041359

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 (C-C) = 0.001 Å
R = 0.039
wR = 0.116
Data-to-parameter ratio = 24.6
Details

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

Kaliyaperumal Thanigaimani,^a Abbas Farhadikoutenaei,^a Nuridayanti Che Khalib,^a Suhana Arshad ^a and Ibrahim Abdul Razak ^a ^*⁺

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

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-HO hydrogen bond, and the two anions are further connected to each other by a pair of N-HO hydrogen bonds with an R₂²(8) ring motif, thus forming a centrosymmetric 2 + 2 aggregate. The aggregates are further linked through weak N-HO and C-HO hydrogen bonds, resulting a three-dimensional network.

Related literature

For details of 2-aminopyridine and its derivatives, see: Banerjee & Murugavel (2004); Bis & Zaworotko (2005); Bis et al. (2006). For details of 6-hydroxypicolinic acid, see: Sun et al. (2004); Soares-Santos et al. (2003). For a related structure, see: Sawada & Ohashi (1998). For hydrogen-bond motifs, see: Bernstein et al. (1995). For bond-length data, see: Allen et al. (1987). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986).

Experimental

Crystal data

C₆H₉N₂⁺·C₆H₄NO₃^-
M_r = 247.25
Monoclinic, P 2₁ /c
a = 11.7093 (6) Å
b = 10.4594 (6) Å
c = 11.4590 (6) Å
= 119.203 (1)°
V = 1225.03 (11) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.957, T_max = 0.978
15984 measured reflections
4430 independent reflections
3745 reflections with I > 2(I)
R_int = 0.027

Refinement

R[F² > 2(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
_max = 0.43 e Å^-3
_min = -0.21 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O1ⁱ	0.899 (15)	2.011 (15)	2.8922 (10)	166.0 (16)
N3-H2N3O1	0.900 (16)	2.245 (19)	3.0373 (12)	146.7 (15)
N3-H2N3O3ⁱ	0.900 (16)	2.408 (16)	3.0916 (11)	133.0 (15)
N3-H1N3O2ⁱⁱ	0.938 (15)	1.884 (16)	2.8071 (12)	167.7 (15)
N2-H1N2O3ⁱ	0.954 (16)	1.686 (18)	2.6206 (11)	165.7 (17)
C3-H3AO1ⁱⁱⁱ	0.95	2.33	3.2598 (11)	166
C9-H9AO1^iv	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); 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: 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.
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.
Bis, J. A., McLaughlin, O. L., Vishweshwar, P. & Zaworoto, M. J. (2006). Cryst. Growth Des. 6, 2648-2650.
Bis, J. A. & Zaworotko, M. J. (2005). Cryst. Growth Des. 5, 1169-1179.
Bruker (2009). SADABS, APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst. 19, 105-107.
Sawada, K. & Ohashi, Y. (1998). Acta Cryst. C54, 1491-1493.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Sun, C. Y., Zheng, X. J. & Jin, L. P. (2004). Z. Anorg. Allg. Chem. 630, 1342-1347.

organic compounds