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Volume 69 
Part 4 
Page o546  
April 2013  

Received 11 March 2013
Accepted 12 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.102
Data-to-parameter ratio = 12.8
Details
Open access

1-(2-Carboxyethyl)-3-(carboxylatomethyl)-2-ethylbenzimidazol-1-ium monohydrate

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

In the title compound, C14H16N2O4·H2O, three substituent groups are located on the same side of the benzimidazole ring plane. In the crystal, O-H...O hydrogen bonds and [pi]-[pi] stacking between parallel imidazole rings [centroid-centroid distance = 3.858 (4) Å] link the molecules into a three-dimensional supramolecular structure.

Related literature

For general background to supramolecular coordination complexes, see: Chakrabarty et al. (2011[Chakrabarty, R., Mukherjee, P.-S. & Stang, P. (2011). Chem. Rev. 111, 6810-6918.]); Cook et al. (2012[Cook, T. R., Zheng, Y.-R. & Stang, P. (2012). Chem. Rev. 113, 734-777.]); Wang et al. (2009[Wang, K.-F., Jian, F.-F., Zhuang, R.-R. & Xiao, H.-L. (2009). Cryst. Growth Des. 9, 3934-3940.], 2010[Wang, X.-J., Cen, Z.-M., Ni, Q.-L., Jiang, X.-F., Lian, H.-C., Gui, L.-C., Zou, H.-H. & Wang, Z.-Y. (2010). Cryst. Growth Des. 10, 2960-2968.]). For related structures, see: Wei et al. (2012[Wei, T.-B., Dang, J.-P., Lin, Q., Yao, H., Liu, Y., Zhang, W.-Q., Ming, J.-J. & Zhang, Y.-M. (2012). Sci. China Ser. B, 55, 2554-2561.]); Chen & Huang (2006[Chen, D.-B. & Huang, L. (2006). Acta Cryst. E62, o4686-o4688.]); Wu et al. (2012[Wu, H.-L., Wang, K.-T., Liu, B., Kou, F., Jia, F., Yuan, J.-K. & Bai, Y.-Y. (2012). Inorg. Chim. Acta 384, 302-308.]).

[Scheme 1]

Experimental

Crystal data
  • C14H16N2O4·H2O

  • Mr = 294.30

  • Triclinic, [P \overline 1]

  • a = 8.286 (7) Å

  • b = 9.041 (8) Å

  • c = 10.629 (9) Å

  • [alpha] = 69.905 (7)°

  • [beta] = 69.096 (7)°

  • [gamma] = 79.082 (8)°

  • V = 696.6 (10) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.26 × 0.23 × 0.22 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2001[Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.973, Tmax = 0.977

  • 5039 measured reflections

  • 2551 independent reflections

  • 1888 reflections with I > 2[sigma](I)

  • Rint = 0.022

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.102

  • S = 1.07

  • 2551 reflections

  • 200 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.23 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H3A...O1i 0.82 1.69 2.474 (2) 160
O5-H1W...O4ii 0.96 (3) 1.89 (3) 2.841 (3) 168 (2)
O5-H2W...O2i 0.90 (3) 1.96 (3) 2.851 (3) 176 (3)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. 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: XU5687 ).


Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 21064006, 21161018 and 21262032), the Program for Changjiang Scholars and Innovative Research Teams in Universities of the Ministry of Education of China (No. IRT1177), the Natural Science Foundation of Gansu Province (No. 1010RJZA018), the Youth Foundation of Gansu Province (No. 1208RJYA048) and NWNU-LKQN-11-32.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Chakrabarty, R., Mukherjee, P.-S. & Stang, P. (2011). Chem. Rev. 111, 6810-6918.  [ISI] [CrossRef] [ChemPort] [PubMed]
Chen, D.-B. & Huang, L. (2006). Acta Cryst. E62, o4686-o4688.  [CSD] [CrossRef] [details]
Cook, T. R., Zheng, Y.-R. & Stang, P. (2012). Chem. Rev. 113, 734-777.  [ISI] [CrossRef] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Wang, X.-J., Cen, Z.-M., Ni, Q.-L., Jiang, X.-F., Lian, H.-C., Gui, L.-C., Zou, H.-H. & Wang, Z.-Y. (2010). Cryst. Growth Des. 10, 2960-2968.  [CSD] [CrossRef] [ChemPort]
Wang, K.-F., Jian, F.-F., Zhuang, R.-R. & Xiao, H.-L. (2009). Cryst. Growth Des. 9, 3934-3940.  [CSD] [CrossRef] [ChemPort]
Wei, T.-B., Dang, J.-P., Lin, Q., Yao, H., Liu, Y., Zhang, W.-Q., Ming, J.-J. & Zhang, Y.-M. (2012). Sci. China Ser. B, 55, 2554-2561.  [CrossRef] [ChemPort]
Wu, H.-L., Wang, K.-T., Liu, B., Kou, F., Jia, F., Yuan, J.-K. & Bai, Y.-Y. (2012). Inorg. Chim. Acta 384, 302-308.  [ISI] [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o546  [ doi:10.1107/S1600536813006855 ]

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