[Journal logo]

Volume 68 
Part 11 
Page o3068  
November 2012  

Received 22 September 2012
Accepted 29 September 2012
Online 6 October 2012

[sj5265sup1]
[3d view]

[Cited in]
[Download citation]
Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.005 Å
R = 0.056
wR = 0.152
Data-to-parameter ratio = 11.8
Details
Open access

A monoclinic polymorph of 5-[(1H-benzimidazol-1-yl)methyl]benzene-1,3-dicarboxylic acid

Hai-Wei Kuaia*

aFaculty of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huaian 223003, People's Republic of China
Correspondence e-mail: hyitshy@126.com

Crystals of the title compound, C16H12N2O4, were obtained accidentally by the hydrothermal reaction of 5-[(1H-benzo[d]imidazol-1-yl)methyl]isophthalic acid with manganese chloride tetrahydrate in the presence of KOH as alkaline reagent for the deprotonation. A triclinic polymorph of this structure has been reported previously from a similar reaction [Cheng (2011[Cheng, X.-C. (2011). Acta Cryst. E67, o3299.]). Acta Cryst. E67, o3299]. The benzimidazole ring system is almost planar, with a maximum deviation from the mean plane of 0.020 (4) Å. The benzimidazole unit and benzene ring are inclined at a dihedral angle of 68.17 (4)°, reflecting the axial rotation of the flexible benzimidazolyl arm. In the crystal, pairs of O-H...O hydrogen bonds link adjacent molecules into inversion dimers. O-H...N contacts connect these dimers into zigzag chains along [010].

Related literature

For a triclinic polymorph of the title compound, see: Cheng (2011[Cheng, X.-C. (2011). Acta Cryst. E67, o3299.]).

[Scheme 1]

Experimental

Crystal data

  • C16H12N2O4

  • Mr = 296.28

  • Monoclinic, P 21 /c

  • a = 7.401 (5) Å

  • b = 16.589 (5) Å

  • c = 11.762 (4) Å

  • [beta] = 111.53 (3)°

  • V = 1343.3 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.20 × 0.10 × 0.10 mm
Data collection

  • Bruker Smart APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.979, Tmax = 0.989

  • 6722 measured reflections

  • 2358 independent reflections

  • 1239 reflections with I > 2[sigma](I)

  • Rint = 0.072
Refinement

  • R[F2 > 2[sigma](F2)] = 0.056

  • wR(F2) = 0.152

  • S = 0.96

  • 2358 reflections

  • 200 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O3-H5...O4i 0.84 1.82 2.649 (3) 171
O1-H4...N1ii 0.84 1.76 2.576 (4) 164
Symmetry codes: (i) -x+2, -y+2, -z+1; (ii) x-1, y, z-1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). 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: DIAMOND (Brandenburg, 2000[Brandenburg, K. (2000). DIAMOND. Crystal Impact GbR, Bonn, Germany.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ5265 ).

References

Brandenburg, K. (2000). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, wisconsin, USA.
Cheng, X.-C. (2011). Acta Cryst. E67, o3299.  [CSD] [CrossRef] [details]
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.  [ISI] [CrossRef] [ChemPort] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2012). E68, o3068  [ doi:10.1107/S1600536812041025 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.