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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 [sigma](C-C) = 0.003 Å
R = 0.048
wR = 0.109
Data-to-parameter ratio = 11.3
Details
Open access

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

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-H...O hydrogen bond occurs. The crystal packing is stabilized by intermolecular O-H...O and C-H...O 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[Gao, S., Huo, L.-H., Zhao, H. & Liu, J.-W. (2005). Acta Cryst. E61, m155-m157.]); Gurunatha et al. (2008[Gurunatha, K.-L., Kazuhiro, U. & Tapas, K.-M. (2008). Inorg. Chem. pp. 6578-6580.]); Wang et al. (2010[Wang, X.-J., Cen, Z.-M. & Ni, Q.-L. (2010). Cryst. Growth Des. 16, 1613-1618.]); Zhang & Li (2010[Zhang, F.-W. & Li, Z.-F. (2010). Inorg. Chem. 49, 3776-3788.]). For related structures, see: Chai et al. (2010[Chai, X.-C., Sun, Y.-Q. & Lei, R. (2010). Cryst. Growth Des. 10, 658-668.]); Liu et al. (2004[Liu, J.-W., Gao, S., Huo, L.-H., Gu, C.-S., Zhao, H. & Zhao, J.-G. (2004). Acta Cryst. E60, m1697-m1699.]); Lu et al. (2006[Lu, W.-G., Jiang, L., Feng, X.-L. & Lu, T. B. (2006). Cryst. Growth Des. 14, 564-571.]).

[Scheme 1]

Experimental

Crystal data
  • C9H8N2O8

  • Mr = 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[alpha] radiation

  • [mu] = 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[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.948, Tmax = 0.957

  • 13878 measured reflections

  • 2091 independent reflections

  • 1750 reflections with I2s(I)

  • Rint = 0.055

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.19 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3W...O2 1.13 (3) 1.29 (3) 2.426 (3) 177 (3)
C1-H1...O6i 0.93 2.47 3.158 (3) 131
C4-H4A...O5ii 0.97 2.38 3.311 (3) 160
C4-H4B...O6i 0.97 2.37 3.046 (3) 126
C6-H6A...O7i 0.97 2.42 3.136 (4) 130
C6-H6B...O8iii 0.97 2.44 3.346 (3) 154
O5-H2W...O1iv 0.92 (3) 1.67 (3) 2.581 (3) 170 (3)
O8-H1W...O4v 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[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). SAINT, APEX2 and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); 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.  [ChemPort]
Gao, S., Huo, L.-H., Zhao, H. & Liu, J.-W. (2005). Acta Cryst. E61, m155-m157.  [CSD] [CrossRef] [details]
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.  [CSD] [CrossRef] [details]
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.  [CrossRef] [details]
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.  [ChemPort] [PubMed]


Acta Cryst (2012). E68, o230  [ doi:10.1107/S160053681105416X ]

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