1H-Imidazol-3-ium-4-carboxyl­ate

Cao, Q.; Duan, B.-R.; Zhu, B.; Cao, Z.

doi:10.1107/S1600536811052998

Volume 68
Part 1
Pages o134-o135
January 2012

Received 28 November 2011
Accepted 9 December 2011
Online 17 December 2011

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.003 Å
R = 0.029
wR = 0.083
Data-to-parameter ratio = 7.0
Details

1H-Imidazol-3-ium-4-carboxylate

Qiang Cao,^a Bao-Rong Duan,^b ^* Bin Zhu ^c and Zhen Cao ^d

^aCollege of Chemistry and Life Science, Weinan Normal University, 714000 Weinan, Shaanxi, People's Republic of China,^bChemistry and Chemical Engineering College, Yantai University, 264005 Yantai, Shandong, People's Republic of China,^cEngineering Company Limited of China Railway and Airport Group, 714000 Weinan, Shaanxi, People's Republic of China, and ^dShaanxi Railway Institute, 714000 Weinan, Shaanxi, People's Republic of China
Correspondence e-mail: ytsxzl@126.com

In the title compound, C₄H₄N₂O₂, both imidazole N atoms are protonated and carboxylate group is deprotonated, resulting in a zwitterion. The molecule is essentially planar, with an r.m.s. deviation of 0.012 (1) Å. In the crystal, N-HO hydrogen bonds and [pi] - [pi] stacking interactions [centroid-centroid distance = 3.674 (2) Å] between the imidazole rings link the molecules into a three-dimensional supramolecular network.

Related literature

For general background to the construction of coordination polymers based on 1H-imidazole-4,5-dicarboxylic acid, see: Alkordi, Liu et al. (2008); Alkordi, Brant et al. (2009); Gu et al. (2010); Lu et al. (2006); Nouar et al. (2009); Wang et al. (2010). For related complexes with 1H-imidazole-4-carboxylic acid, see: Haggag (2005); Starosta & Leciejewicz (2006); Gryz et al. (2007); Yin et al. (2009); Shuai et al. (2011); Zheng et al. (2011). For the synthesis of 1H-imidazole-4-carboxylic acid, see: Davis et al. (1982).

Experimental

Crystal data

C₄H₄N₂O₂
M_r = 112.09
Orthorhombic, P n a 2₁
a = 10.474 (6) Å
b = 11.676 (7) Å
c = 3.674 (2) Å
V = 449.3 (5) Å³
Z = 4
Mo K radiation
= 0.14 mm^-1
T = 298 K
0.25 × 0.21 × 0.18 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) T_min = 0.967, T_max = 0.976
2280 measured reflections
510 independent reflections
480 reflections with I > 2(I)
R_int = 0.023

Refinement

R[F² > 2(F²)] = 0.029
wR(F²) = 0.083
S = 1.10
510 reflections
73 parameters
1 restraint
H-atom parameters constrained
_max = 0.12 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O2ⁱ	0.86	1.82	2.648 (2)	160
N1-H1O1ⁱⁱ	0.86	1.91	2.736 (2)	161
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[-x, -y+1, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LD2040 ).

Acknowledgements

The authors gratefully acknowledge the Scientific Research Foundation of Weinan Normal University (grant No. 07YKZ027), the Natural Science Foundation of Yantai University (grant No. HY10Z10), the Science and Technology Research Projects of Yantai City (grant No. 2006GGAO00143), the Science and Technology Research Projects of Shandong Province (grant No. 2008 GG10003020) and the National Science and Technology Research Projects (grant No. 2004BA320B) for supporting this work.

References

Alkordi, M. H., Brant, J. A., Wojtas, L., Kravtsov, V. Ch., Cairns, A. J. & Eddaoudi, M. (2009). J. Am. Chem. Soc. 131, 17753-17755.
Alkordi, M. H., Liu, Y. L., Larsen, R. W., Eubank, J. F. & Eddaoudi, M. (2008). J. Am. Chem. Soc. 130, 12639-12641.
Bruker (2008). APEX2 and SAINT. Bruker AXSInc., Madison, Wisconsin, USA.
Davis, D. P., Kirk, K. L. & Cohen, L. A. (1982). J. Heterocycl. Chem. 19, 253-256.
Gryz, M., Starosta, W. & Leciejewicz, J. (2007). J. Coord. Chem. 60, 539-546.
Gu, Z. G., Cai, Y. P., Fang, H. C., Zhou, Z. Y., Thallapally, P. K., Tian, J., Liu, J. & Exarhos, G. J. (2010). Chem. Commun. 46, 5373-5375.
Haggag, S. S. (2005). Egypt. J. Chem. 48, 27-41.
Lu, W. G., Su, C. Y., Lu, T. B., Jiang, L. & Chen, J. M. (2006). J. Am. Chem. Soc. 128, 34-35.
Nouar, F., Eckert, J., Eubank, J. F., Forster, P. & Eddaoudi, M. (2009). J. Am. Chem. Soc. 131, 2864-2870.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shuai, W., Cai, S. & Zheng, S. (2011). Acta Cryst. E67, m897.
Starosta, W. & Leciejewicz, J. (2006). Acta Cryst. E62, m2648-m2650.
Wang, S., Zhao, T. T., Li, G. H., Wojtas, L., Huo, Q. S., Eddaoudi, M. & Liu, Y. L. (2010). J. Am. Chem. Soc. 132, 18038-18041.
Yin, W. P., Li, Y. G., Mei, X. L. & Yao, J. C. (2009). Chin. J. Struct. Chem. 28, 1155-1159.
Zheng, S., Cai, S., Fan, J. & Zhang, W. (2011). Acta Cryst. E67, m865.

organic compounds