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Volume 69 
Part 6 
Pages o837-o838  
June 2013  

Received 25 April 2013
Accepted 1 May 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.002 Å
R = 0.034
wR = 0.088
Data-to-parameter ratio = 15.4
Details
Open access

Methyl 2-(2-methyl-4-nitro-1H-imidazol-1-yl)acetate

aLaboratoire des Produits Naturels d'Origine Végétale et de Synthèse Organique, PHYSYNOR, Université Constantine, 25000 Constantine, Algeria,bUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale, CHEMS, Université Constantine, 25000 Constantine, Algeria,cDépartement des Sciences de la Matière, Faculté des Sciences Exactes et Sciences de la Nature et de la Vie, Université Oum El Bouaghi, 04000 Oum El Bouaghi, Algeria, and dCentre de Diffractométrie X, UMR 6226 CNRS, Unité Sciences Chimiques de Rennes, Université de Rennes I, 263 Avenue du Général Leclerc, 35042 Rennes, France
Correspondence e-mail: bouacida_sofiane@yahoo.fr

In the crystal of the title compound, C7H9N3O4, molecules are linked by weak C-H...O hydrogen bonds into chains along the a-axis direction. The dihedral angle between the ring and the nitro group is 3.03 (6), while that between the ring and the acetate group is 85.01 (3)°.

Related literature

For the synthesis of the title compound, see: Pavlik et al. (2011[Pavlik, C., Biswal, N. C., Gaenzler, F. C., Morton, M. D., Kuhn, L. T., Claffey, K. P., Zhu, Q. & Smith, M. B. (2011). Dyes Pigm. 89, 9-15.]); Kasai et al. (2001[Kasai, S., Nagasawa, H., Yamashita, M., Masui, M., Kuwasaka, H., Oshodani, T., Uto, Y., Inomata, T., Oka, S., Inayama, S. & Hori, H. (2001). Bioorg. Med. Chem. 9, 453-464.]). For the structural identification of nitroimidazoles, see: Larina & Lopyrev (2009[Larina, L. & Lopyrev, V. (2009). Nitroazoles: Synthesis, Structure and Applications, in Topics in Applied Chemistry, edited by A. Katritzky & G. J. Sabongi. Berlin: Springer.]). For biological activities of this class of compounds, see: Gaonkar et al. (2009[Gaonkar, S. L., Rai, K. M. L. & Shetty, N. S. (2009). Med. Chem. Res. 18, 221-230.]); Olender et al. (2009[Olender, D., Zwawiak, J., Lukianchuk, V., Lesyk, R., Kropacz, A., Fojutowski, A. & Zaprutko, L. (2009). Eur. J. Med. Chem. 44, 645-652.]). For our previous work on imidazole derivatives, see: Chelghoum et al. (2011[Chelghoum, M., Bahnous, M., Bouacida, S., Roisnel, T. & Belfaitah, A. (2011). Acta Cryst. E67, o1890.]); Bahnous et al. (2012[Bahnous, M., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2012). Acta Cryst. E68, o1391.]).

[Scheme 1]

Experimental

Crystal data
  • C7H9N3O4

  • Mr = 199.17

  • Monoclinic, P 21 /c

  • a = 4.6619 (2) Å

  • b = 17.3256 (7) Å

  • c = 11.1490 (4) Å

  • [beta] = 103.204 (2)°

  • V = 876.70 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 150 K

  • 0.35 × 0.3 × 0.12 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2002[Bruker, (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.937, Tmax = 0.985

  • 7665 measured reflections

  • 1991 independent reflections

  • 1753 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.034

  • wR(F2) = 0.088

  • S = 1.09

  • 1991 reflections

  • 129 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.21 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C5-H5A...O4i 0.99 2.30 3.2350 (16) 156
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2004[Bruker, (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2004[Bruker, (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005[Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and DIAMOND (Brandenburg & Berndt, 2001[Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CRYSCAL (local program).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: YK2093 ).


Acknowledgements

The authors are grateful to all the personnel of the research team `Synthèse de molécules à objectif thérapeutique' of the PHYSYNOR Laboratory, Université Constantine, Algeria, for their assistance. Thanks are due to the MESRS (Ministére de l'Enseignement Supérieur et de la Recherche Scientifique, Algerie) for financial support.

References

Bahnous, M., Bouraiou, A., Bouacida, S., Roisnel, T. & Belfaitah, A. (2012). Acta Cryst. E68, o1391.  [CSD] [CrossRef] [details]
Brandenburg, K. & Berndt, M. (2001). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker, (2002). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker, (2004). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Burla, M. C., Caliandro, R., Camalli, M., Carrozzini, B., Cascarano, G. L., De Caro, L., Giacovazzo, C., Polidori, G. & Spagna, R. (2005). J. Appl. Cryst. 38, 381-388.  [ISI] [CrossRef] [ChemPort] [details]
Chelghoum, M., Bahnous, M., Bouacida, S., Roisnel, T. & Belfaitah, A. (2011). Acta Cryst. E67, o1890.  [CSD] [CrossRef] [details]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gaonkar, S. L., Rai, K. M. L. & Shetty, N. S. (2009). Med. Chem. Res. 18, 221-230.  [ISI] [CrossRef] [ChemPort]
Kasai, S., Nagasawa, H., Yamashita, M., Masui, M., Kuwasaka, H., Oshodani, T., Uto, Y., Inomata, T., Oka, S., Inayama, S. & Hori, H. (2001). Bioorg. Med. Chem. 9, 453-464.  [CrossRef] [PubMed] [ChemPort]
Larina, L. & Lopyrev, V. (2009). Nitroazoles: Synthesis, Structure and Applications, in Topics in Applied Chemistry, edited by A. Katritzky & G. J. Sabongi. Berlin: Springer.
Olender, D., Zwawiak, J., Lukianchuk, V., Lesyk, R., Kropacz, A., Fojutowski, A. & Zaprutko, L. (2009). Eur. J. Med. Chem. 44, 645-652.  [ISI] [CrossRef] [PubMed] [ChemPort]
Pavlik, C., Biswal, N. C., Gaenzler, F. C., Morton, M. D., Kuhn, L. T., Claffey, K. P., Zhu, Q. & Smith, M. B. (2011). Dyes Pigm. 89, 9-15.  [CrossRef] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]


Acta Cryst (2013). E69, o837-o838   [ doi:10.1107/S1600536813011914 ]

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