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Volume 69 
Part 3 
Page o431  
March 2013  

Received 18 February 2013
Accepted 19 February 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.057
wR = 0.168
Data-to-parameter ratio = 13.4
Details
Open access

1-Allyl-5-nitro-1H-benzimidazol-2(3H)-one

aLaboratoire de Chimie Organique Appliquée, Université Sidi Mohamed Ben Abdallah, Faculté des Sciences et Techniques, Route d'immouzzer, BP 2202 Fès, Morocco,bLaboratoire de Chimie Organique Hétérocyclique URAC21, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco,cINANOTECH (Institute of Nanomaterials and Nanotechnology), MAScIR, Av. de l'Armée Royale, Rabat, Morocco, and dLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: ouzidan@yahoo.fr

The benzimidazolone residue in the title molecule, C10H9N3O3, is almost planar, with the largest deviation from the mean plane being 0.016 (2) Å for the C atom linked to the nitro group. This plane is nearly perpendicular to the 1-allyl chain as indicated by the C-N-C-C torsion angle of 90.9 (3)°. The fused-ring system makes a dihedral angle of 5.6 (3)° with the nitro group, leading to a synperiplanar conformation. In the crystal, zigzag supramolecular chains are formed along the a axis by N-H...O hydrogen bonds.

Related literature

For pharmacological and biochemical properties of benzimidazoles and derivatives, see: Al Muhaimeed (1997[Al Muhaimeed, H. (1997). J. Int. Med. Res. 25, 175-181.]); Scott et al. (2002[Scott, L. J., Dunn, C. J., Mallarkey, G. & Sharpe, M. (2002). Drugs, 62, 1503-1538.]); Nakano et al. (2000[Nakano, H., Inoue, T., Kawasaki, N., Miyataka, H., Matsumoto, H., Taguchi, T., Inagaki, N., Nagai, H. & Satoh, T. (2000). Bioorg. Med. Chem. 8, 373-380.]); Zhu et al. (2000[Zhu, Z., Lippa, B., Drach, J. C. & Townsend, L. B. (2000). J. Med. Chem. 43, 2430-2437.]); Zarrinmayeh et al. (1998[Zarrinmayeh, H., Nunes, A. M., Ornstein, P. L., Zimmerman, D. M., Arnold, M. B., Schober, D. A., Gackenheimer, S. L., Bruns, R. F., Hipskind, P. A., Britton, T. C., Cantrell, B. E. & Gehlert, D. R. (1998). J. Med. Chem. 41, 2709-2719.]). For related structures, see: Ouzidan et al. (2011a[Ouzidan, Y., Kandri Rodi, Y., Butcher, R. J., Essassi, E. M. & El Ammari, L. (2011a). Acta Cryst. E67, o283.],b[Ouzidan, Y., Kandri Rodi, Y., Saffon, N., Essassi, E. M. & Ng, S. W. (2011b). Acta Cryst. E67, o520.]).

[Scheme 1]

Experimental

Crystal data
  • C10H9N3O3

  • Mr = 219.20

  • Orthorhombic, P b c a

  • a = 8.3246 (3) Å

  • b = 14.9567 (6) Å

  • c = 16.4461 (7) Å

  • V = 2047.68 (14) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 296 K

  • 0.46 × 0.31 × 0.18 mm

Data collection
  • Bruker X8 APEXII area-detector diffractometer

  • 12145 measured reflections

  • 1940 independent reflections

  • 1483 reflections with I > 2[sigma](I)

  • Rint = 0.030

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.168

  • S = 1.05

  • 1940 reflections

  • 145 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.60 e Å-3

  • [Delta][rho]min = -0.38 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2N...O3i 0.86 1.96 2.801 (3) 164
Symmetry code: (i) [x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). 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: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5200 ).


Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray data measurements.

References

Al Muhaimeed, H. (1997). J. Int. Med. Res. 25, 175-181.  [ChemPort] [PubMed]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Nakano, H., Inoue, T., Kawasaki, N., Miyataka, H., Matsumoto, H., Taguchi, T., Inagaki, N., Nagai, H. & Satoh, T. (2000). Bioorg. Med. Chem. 8, 373-380.  [CrossRef] [PubMed] [ChemPort]
Ouzidan, Y., Kandri Rodi, Y., Butcher, R. J., Essassi, E. M. & El Ammari, L. (2011a). Acta Cryst. E67, o283.  [CSD] [CrossRef] [details]
Ouzidan, Y., Kandri Rodi, Y., Saffon, N., Essassi, E. M. & Ng, S. W. (2011b). Acta Cryst. E67, o520.  [CSD] [CrossRef] [details]
Scott, L. J., Dunn, C. J., Mallarkey, G. & Sharpe, M. (2002). Drugs, 62, 1503-1538.  [ISI] [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zarrinmayeh, H., Nunes, A. M., Ornstein, P. L., Zimmerman, D. M., Arnold, M. B., Schober, D. A., Gackenheimer, S. L., Bruns, R. F., Hipskind, P. A., Britton, T. C., Cantrell, B. E. & Gehlert, D. R. (1998). J. Med. Chem. 41, 2709-2719.  [ISI] [CrossRef] [ChemPort] [PubMed]
Zhu, Z., Lippa, B., Drach, J. C. & Townsend, L. B. (2000). J. Med. Chem. 43, 2430-2437.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o431  [ doi:10.1107/S1600536813004790 ]

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