5-Carb­oxy-1,3-bis­(carb­oxy­meth­yl)-4-imidazolinium-4-carboxyl­ate

Zhang, Y.-M.; Ming, J.-J.; Dang, J.-P.; Zhang, W.-Q.; Wei, T.-B.

doi:10.1107/S160053681105416X

Volume 68
Part 1
Page o230
January 2012

Received 9 December 2011
Accepted 16 December 2011
Online 23 December 2011

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.048
wR = 0.109
Data-to-parameter ratio = 11.3
Details

5-Carboxy-1,3-bis(carboxymethyl)-4-imidazolinium-4-carboxylate

You-Ming Zhang,^a Jian-Jun Ming,^a Jian-Peng Dang,^a Wan-Qiang Zhang ^a and Tai-Bao Wei ^a ^*

^aCollege of Chemistry and Chemical Engineering, Key Laboratory of Eco-Environment-Related Polymer Materials of the Ministry of Education, Gansu Key Laboratory of Polymer Materials, Northwest Normal University, Lanzhou 730070, People's Republic of China
Correspondence e-mail: weitaibao@126.com

The title compound, C₉H₈N₂O₈, was obtained by the reaction of imidazole-4,5-dicarboxylic acid and 2-chloroacetic acid. An intramolecular O-HO hydrogen bond occurs. The crystal packing is stabilized by intermolecular O-HO and C-HO hydrogen bonds, which link molecules into a three-dimensional network.

Related literature

The title compound is a potential polydentate ligand for the construction of metal-organic frameworks. For applications of metal-organic frameworks, see: Gao et al. (2005); Gurunatha et al. (2008); Wang et al. (2010); Zhang & Li (2010). For related structures, see: Chai et al. (2010); Liu et al. (2004); Lu et al. (2006).

Experimental

Crystal data

C₉H₈N₂O₈
M_r = 272.17
Orthorhombic, P b c a
a = 8.986 (7) Å
b = 7.041 (6) Å
c = 33.68 (3) Å
V = 2131 (3) Å³
Z = 8
Mo K radiation
= 0.15 mm^-1
T = 296 K
0.35 × 0.33 × 0.29 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008) T_min = 0.948, T_max = 0.957
13878 measured reflections
2091 independent reflections
1750 reflections with I2s(I)
R_int = 0.055

Refinement

R[F² > 2(F²)] = 0.048
wR(F²) = 0.109
S = 0.98
2091 reflections
185 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.23 e Å^-3
_min = -0.19 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O3-H3WO2	1.13 (3)	1.29 (3)	2.426 (3)	177 (3)
C1-H1O6ⁱ	0.93	2.47	3.158 (3)	131
C4-H4AO5ⁱⁱ	0.97	2.38	3.311 (3)	160
C4-H4BO6ⁱ	0.97	2.37	3.046 (3)	126
C6-H6AO7ⁱ	0.97	2.42	3.136 (4)	130
C6-H6BO8ⁱⁱⁱ	0.97	2.44	3.346 (3)	154
O5-H2WO1^iv	0.92 (3)	1.67 (3)	2.581 (3)	170 (3)
O8-H1WO4^v	0.93 (4)	1.84 (4)	2.710 (3)	155 (3)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ ; (ii) $[x-{\script{1\over 2}}, y, -z+{\script{1\over 2}}]$ ; (iii) -x, -y, -z+1; (iv) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ .

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: RZ2687 ).

Acknowledgements

This work was supported by the NSFC (No. 21064006) and the Natural Science Foundation of Gansu (1010RJZA018), which are gratefully acknowledged.

References

Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chai, X.-C., Sun, Y.-Q. & Lei, R. (2010). Cryst. Growth Des. 10, 658-668.
Gao, S., Huo, L.-H., Zhao, H. & Liu, J.-W. (2005). Acta Cryst. E61, m155-m157.
Gurunatha, K.-L., Kazuhiro, U. & Tapas, K.-M. (2008). Inorg. Chem. pp. 6578-6580.
Liu, J.-W., Gao, S., Huo, L.-H., Gu, C.-S., Zhao, H. & Zhao, J.-G. (2004). Acta Cryst. E60, m1697-m1699.
Lu, W.-G., Jiang, L., Feng, X.-L. & Lu, T. B. (2006). Cryst. Growth Des. 14, 564-571.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Wang, X.-J., Cen, Z.-M. & Ni, Q.-L. (2010). Cryst. Growth Des. 16, 1613-1618.
Zhang, F.-W. & Li, Z.-F. (2010). Inorg. Chem. 49, 3776-3788.

organic compounds