3-(4-Carb­oxy-5-carboxyl­ato-1H-imidazol-2-yl)pyridin-1-ium monohydrate

Liu, G.-J.; Zhao, G.-W.; Li, L.; Gao, H.-T.

doi:10.1107/S1600536811002248

Volume 67
Part 2
Page o488
February 2011

Received 10 January 2011
Accepted 14 January 2011
Online 26 January 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.042
wR = 0.119
Data-to-parameter ratio = 9.9
Details

3-(4-Carboxy-5-carboxylato-1H-imidazol-2-yl)pyridin-1-ium monohydrate

Guang-Jun Liu,^a Guang-Wang Zhao,^a Li Li ^b and Hong-Tao Gao ^a ^*

^aDepartment of Chemisry and Chemical Engineering, Jining University, 273155 Qufu, Shandong, People's Republic of China, and ^bShandong Lukang Pharmaceutical Group Co. Ltd, 272100 Jining, Shandong, People's Republic of China
Correspondence e-mail: gaohongtao@gmail.com

In the zwitterionic molecule of the title compound, C₁₀H₇N₃O₄·H₂O, one carboxyl group is deprotonated and the pyridine N atom is protonated. The pyridinium and imidazole rings form a dihedral angle of 5.23 (1)°. An intramolecular O-HO hydrogen bond occurs. In the crystal, intermolecular N-HO, O-HN and O-HO hydrogen bonds link the zwitterions and water molecules into sheets parallel to (102).

Related literature

For the use of 4,5-imidazoledicarboxylic acid in coordination chemistry and for related structures, see: Sun et al. (2006); Chen (2008); Liu et al. (2009). For the synthesis of the title compound, see: Lebedev et al. (2007). For bond-length data, see: Allen et al. (1987).

Experimental

Crystal data

C₁₀H₇N₃O₄·H₂O
M_r = 251.20
Monoclinic, P 2₁ /c
a = 3.7342 (18) Å
b = 16.354 (8) Å
c = 16.634 (8) Å
= 97.019 (10)°
V = 1008.2 (8) Å³
Z = 4
Mo K radiation
= 0.14 mm^-1
T = 298 K
0.32 × 0.28 × 0.25 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005) T_min = 0.958, T_max = 0.967
5038 measured reflections
1777 independent reflections
1314 reflections with I > 2(I)
R_int = 0.028

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.119
S = 1.14
1777 reflections
179 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.21 e Å^-3
_min = -0.18 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O4ⁱ	0.98 (2)	1.87 (2)	2.824 (3)	164.8 (16)
N3-H3O1Wⁱⁱ	0.99 (3)	1.66 (3)	2.625 (3)	163 (2)
O1W-H1AO3ⁱⁱⁱ	0.94 (4)	1.84 (4)	2.782 (3)	176 (4)
O1W-H1BO1	0.95 (4)	2.50 (4)	3.032 (3)	115 (3)
O1W-H1BN2	0.95 (4)	1.90 (4)	2.839 (2)	166 (3)
O2-H2O3	0.82	1.67	2.493 (2)	179
Symmetry codes: (i) -x+3, -y+2, -z+1; (ii) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); 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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5038 ).

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.
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chen, L.-Z. (2008). Acta Cryst. E64, m1286.
Lebedev, A. V., Lebedev, A. B., Sheludyakov, V. D., Kovaleva, E. A., Ustinova, O. L. & Shatunov, V. V. (2007). Russ. J. Gen. Chem. 77, 949-953.
Liu, W., Zhang, G., Li, X., Wu, B.-L. & Zhang, H.-Y. (2009). Acta Cryst. E65, m938-m939.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Sun, T., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2006). Acta Cryst. E62, o2751-o2752.

organic compounds