2-Amino-4-methyl­pyridinium 6-carb­oxy­pyridine-2-carboxyl­ate methanol monosolvate

Aghabozorg, H.; Mofidi Rouchi, A.; Mirzaei, M.; Notash, B.

doi:10.1107/S1600536810050245

Volume 67
Part 1
Page o54
January 2011

Received 21 November 2010
Accepted 1 December 2010
Online 8 December 2010

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.004 Å
R = 0.079
wR = 0.216
Data-to-parameter ratio = 18.0
Details

2-Amino-4-methylpyridinium 6-carboxypyridine-2-carboxylate methanol monosolvate

Hossein Aghabozorg,^a ^* Azadeh Mofidi Rouchi,^a Masoud Mirzaei ^b and Behrouz Notash ^c

^aFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran,^bDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad, Iran, and ^cDepartment of Chemistry, Shahid Beheshti University, G.C., Evin, Tehran 1983963113, Iran
Correspondence e-mail: haghabozorg@yahoo.com

In the title solvated molecular salt, C₆H₉N₂⁺·C₇H₄NO₄^-·CH₄O, the pyridine N atom of 2-amino-4-methylpyridine is protonated and one carboxyl group of pyridine-2,6-dicarboxylic acid is deprotonated. The dihedral angles between the -CO₂ and -COH groups and the pyridine ring are 0.65 (13) and 7.4°. The crystal packing is stabilized by intermolecular N-HO, O-HO and weak C-HO hydrogen bonds.

Related literature

For background to proton-transfer compounds, see: Aghabozorg et al. (2008). For related structures, see: Aakeröy et al. (1998); Aghabozorg et al. (2006); Al-Allaf et al. (2003); Fu et al. (2005); Linden et al. (2003); Moghimi et al. (2004); Sheshmani et al. (2006); Thanigaimani et al. (2007).

Experimental

Crystal data

C₆H₉N₂⁺·C₇H₄NO₄^-·CH₄O
M_r = 307.31
Triclinic, $[P \overline 1]$
a = 7.2191 (14) Å
b = 9.5095 (19) Å
c = 11.139 (2) Å
= 94.44 (3)°
= 99.76 (3)°
= 92.50 (3)°
V = 750.1 (3) Å³
Z = 2
Mo K radiation
= 0.11 mm^-1
T = 298 K
0.4 × 0.25 × 0.2 mm

Data collection

Stoe IPDS II diffractometer
8658 measured reflections
4005 independent reflections
2697 reflections with I > 2(I)
R_int = 0.058

Refinement

R[F² > 2(F²)] = 0.079
wR(F²) = 0.216
S = 1.17
4005 reflections
222 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.44 e Å^-3
_min = -0.26 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C14-H14CO2ⁱ	0.96	2.59	3.488 (5)	157
O5-H5AO3ⁱⁱ	0.78 (5)	2.02 (5)	2.796 (3)	170 (4)
N3-H3BO4ⁱⁱⁱ	0.83 (4)	1.95 (4)	2.764 (3)	166 (3)
N3-H3AO2ⁱ	0.87 (4)	2.30 (4)	3.122 (3)	158 (3)
N2-H2O3ⁱⁱⁱ	0.85 (3)	1.87 (3)	2.723 (3)	173 (3)
O1-H1O5^iv	0.87 (4)	1.87 (4)	2.689 (3)	156 (4)
Symmetry codes: (i) x, y+1, z; (ii) x+1, y+1, z; (iii) x+1, y, z; (iv) x-1, y-1, z.

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5416 ).

Acknowledgements

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

References

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Aghabozorg, H., Ghadermazi, M. & Sadr-Khanlou, E. (2006). Anal. Sci. 22, x253-x254.
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Linden, A., Petridis, A. & James, B. D. (2003). Helv. Chim. Acta, 86, 711-725.
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Sheshmani, S., Ghadermazi, M. & Aghabozorg, H. (2006). Acta Cryst. E62, o3620-o3622.
Stoe & Cie (2005). X-AREA. Stoe & Cie, Darmstadt, Germany.
Thanigaimani, K., Muthiah, P. T. & Lynch, D. E. (2007). Acta Cryst. C63, o295-o300.

organic compounds