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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 [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.119
Data-to-parameter ratio = 9.9
Details
Open access

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

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-H...O hydrogen bond occurs. In the crystal, intermolecular N-H...O, O-H...N and O-H...O 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[Sun, T., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2006). Acta Cryst. E62, o2751-o2752.]); Chen (2008[Chen, L.-Z. (2008). Acta Cryst. E64, m1286.]); Liu et al. (2009[Liu, W., Zhang, G., Li, X., Wu, B.-L. & Zhang, H.-Y. (2009). Acta Cryst. E65, m938-m939.]). For the synthesis of the title compound, see: Lebedev et al. (2007[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.]). 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.]).

[Scheme 1]

Experimental

Crystal data
  • C10H7N3O4·H2O

  • Mr = 251.20

  • Monoclinic, P 21 /c

  • a = 3.7342 (18) Å

  • b = 16.354 (8) Å

  • c = 16.634 (8) Å

  • [beta] = 97.019 (10)°

  • V = 1008.2 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.958, Tmax = 0.967

  • 5038 measured reflections

  • 1777 independent reflections

  • 1314 reflections with I > 2[sigma](I)

  • Rint = 0.028

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.18 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O4i 0.98 (2) 1.87 (2) 2.824 (3) 164.8 (16)
N3-H3...O1Wii 0.99 (3) 1.66 (3) 2.625 (3) 163 (2)
O1W-H1A...O3iii 0.94 (4) 1.84 (4) 2.782 (3) 176 (4)
O1W-H1B...O1 0.95 (4) 2.50 (4) 3.032 (3) 115 (3)
O1W-H1B...N2 0.95 (4) 1.90 (4) 2.839 (2) 166 (3)
O2-H2...O3 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[Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). APEX2, SAINT and SADABS. 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.


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.  [CSD] [CrossRef] [details]
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.  [ISI] [CrossRef] [ChemPort]
Liu, W., Zhang, G., Li, X., Wu, B.-L. & Zhang, H.-Y. (2009). Acta Cryst. E65, m938-m939.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Sun, T., Ma, J.-P., Huang, R.-Q. & Dong, Y.-B. (2006). Acta Cryst. E62, o2751-o2752.  [CSD] [CrossRef] [details]


Acta Cryst (2011). E67, o488  [ doi:10.1107/S1600536811002248 ]

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