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Volume 69 
Part 4 
Page o552  
April 2013  

Received 2 March 2013
Accepted 7 March 2013
Online 16 March 2013

Key indicators
Single-crystal X-ray study
T = 273 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.122
Data-to-parameter ratio = 13.4
Details
Open access

1-(2-Methyl-5-nitro-1H-imidazol-1-yl)acetone

aH.E.J. Research Institute of Chemistry, International Center for Chemical and Biological Sciences, University of Karachi, Karachi 75270, Pakistan,bPCSIR Laboratories Complex Karachi, Shahrah-e-Dr Salimuzzaman Siddiqui, Karachi 75280, Pakistan, and cRipha Insititue of Pharmaceutical Sciences, Ripha International University, 7th Avenue G-7/4 Islamambad, Pakistan
Correspondence e-mail: dr.sammer.yousuf@gmail.com

In the molecule of the title compound, C7H9N3O3, the nitro and carbonyl groups are tilted with respect to the imidazole ring by 9.16 (6) and 65.47 (7)°, respectively. Neighbouring chains are linked via C-H...N and C-H...O hydrogen bonds forming two-dimensional slab-like networks lying parallel to (01-1).

Related literature

For the antibiotic properties of metronidazole and mecnidazole, see: Lin et al. (2012[Lin, Y., Su, Y., Liao, X., Yang, N., Yang, X. & Choi, M. M. F. (2012). Talanta, 88, 646-652.]); Almirall et al. (2011[Almirall, P., Escobedo, A. A., Ayala, I., Alfonso, M., Salazar, Y., Cañete, R., Cimerman, S., Galloso, M., Olivero, I., Robaina, M. & Tornés, K. (2011). J. Parasitol. Res., Article ID 636857, doi:10.1155/2011/636857.]); Zhang et al. (2011[Zhang, H.-J., Zhu, D.-D., Li, Z.-L., Sun, J. & Zhu, H. L. (2011). Bioorg. Med. Chem. 19, 4513-4519.]). For the crystal structure of related imidazoles, see: Yousuf et al. (2012[Yousuf, S., Zeb, A., Batool, F. & Basha, F. Z. (2012). Acta Cryst. E68, o2781.]); Zeb et al. (2012[Zeb, A., Yousuf, S. & Basha, F. Z. (2012). Acta Cryst. E68, o1218.]).

[Scheme 1]

Experimental

Crystal data
  • C7H9N3O3

  • Mr = 183.17

  • Monoclinic, P 21 /n

  • a = 4.7548 (4) Å

  • b = 12.3971 (9) Å

  • c = 14.8580 (11) Å

  • [beta] = 97.350 (2)°

  • V = 868.62 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 273 K

  • 0.52 × 0.33 × 0.24 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.944, Tmax = 0.974

  • 5030 measured reflections

  • 1614 independent reflections

  • 1328 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.122

  • S = 1.06

  • 1614 reflections

  • 120 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C2-H2B...N2i 0.93 2.56 3.361 (2) 144
C5-H5B...O2ii 0.97 2.57 3.527 (2) 167
C7-H7B...O3iii 0.96 2.49 3.340 (2) 147
Symmetry codes: (i) -x-1, -y+1, -z+1; (ii) [-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x+1, y, z.

Data collection: SMART (Bruker, 2000[Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SADABS, SMART 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, PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ5048 ).


Acknowledgements

The authors gratefully acknowledge the Pakistan Academy of Sciences for funding project No. 5-9/PAS/8418 entitled `Biology-oriented Parallel Synthesis on Nitroimidazoles in Search of Better Therapeutic Agents'.

References

Almirall, P., Escobedo, A. A., Ayala, I., Alfonso, M., Salazar, Y., Cañete, R., Cimerman, S., Galloso, M., Olivero, I., Robaina, M. & Tornés, K. (2011). J. Parasitol. Res., Article ID 636857, doi:10.1155/2011/636857.
Bruker (2000). SADABS, SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Lin, Y., Su, Y., Liao, X., Yang, N., Yang, X. & Choi, M. M. F. (2012). Talanta, 88, 646-652.  [ISI] [CrossRef] [ChemPort] [PubMed]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yousuf, S., Zeb, A., Batool, F. & Basha, F. Z. (2012). Acta Cryst. E68, o2781.  [CSD] [CrossRef] [details]
Zeb, A., Yousuf, S. & Basha, F. Z. (2012). Acta Cryst. E68, o1218.  [CSD] [CrossRef] [details]
Zhang, H.-J., Zhu, D.-D., Li, Z.-L., Sun, J. & Zhu, H. L. (2011). Bioorg. Med. Chem. 19, 4513-4519.  [CrossRef] [ChemPort] [PubMed]


Acta Cryst (2013). E69, o552  [ doi:10.1107/S1600536813006569 ]

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