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Volume 64 
Part 2 
Page o472  
February 2008  

Received 19 December 2007
Accepted 12 January 2008
Online 18 January 2008

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Key indicators
Single-crystal X-ray study
T = 294 K
Mean [sigma](C-C) = 0.005 Å
R = 0.067
wR = 0.175
Data-to-parameter ratio = 14.8
Details
Open access

2-[1-Chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-yloxycarbonyl]benzoic acid

Xiao Tao,a Lin Yuan,a Xiao-Qing Zhangb and Jin-Tang Wanga*

aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, Nanjing 210009, People's Republic of China, and bNanjing Huawei Medicinal Science Development Co. Ltd, Nanjing 210036, People's Republic of China
Correspondence e-mail: wjt@njut.edu.cn

The asymmetric unit of the title compound, C15H14ClN3O6, contains two independent molecules. The imidazole rings are oriented with respect to the benzene rings at dihedral angles of 19.66 (3) and 21.64 (3)°. In the crystal structure, intermolecular O-H...N hydrogen bonds link the molecules into infinite chains.

Related literature

For bond-length data, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • C15H14ClN3O6

  • Mr = 367.74

  • Monoclinic, P 21 /c

  • a = 15.214 (3) Å

  • b = 16.271 (3) Å

  • c = 15.069 (3) Å

  • [beta] = 113.86 (3)°

  • V = 3411.5 (14) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.26 mm-1

  • T = 294 (2) K

  • 0.40 × 0.30 × 0.20 mm
Data collection

  • Enraf-Nonius CAD-4 diffractometer

  • Absorption correction: [psi] scan (North et al., 1968[North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.]) Tmin = 0.903, Tmax = 0.950

  • 6938 measured reflections

  • 6682 independent reflections

  • 3559 reflections with I > 2[sigma](I)

  • Rint = 0.037

  • 3 standard reflections frequency: 120 min intensity decay: none
Refinement

  • R[F2 > 2[sigma](F2)] = 0.066

  • wR(F2) = 0.175

  • S = 1.02

  • 6682 reflections

  • 451 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
O1-H1B...N5i 0.82 1.81 2.623 (3) 172
O7-H7A...N2ii 0.82 1.82 2.621 (3) 166
Symmetry codes: (i) [-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]; (ii) [-x, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: CAD-4 Software (Enraf-Nonius, 1989[Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft, The Netherlands.]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995[Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.]); 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: HK2413 ).

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Enraf-Nonius (1989). CAD-4 Software. Version 5. Enraf-Nonius, Delft, The Netherlands.
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany.
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351-359.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]

Acta Cryst (2008). E64, o472  [ doi:10.1107/S1600536808001268 ]

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.