[Journal logo]

Volume 68 
Part 11 
Page o3212  
November 2012  

Received 9 October 2012
Accepted 21 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.045
wR = 0.128
Data-to-parameter ratio = 21.4
Details
Open access

1-Allyl-1H-1,3-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,cInstitute of Nanmaterials and Nanotechnology, MASCIR, 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: d_belaziz@yahoo.fr

The fused five- and six-membered rings in the title compound, C10H10N2O, are approximately coplanar, with an r.m.s. deviation of 0.008 Å. The mean plane of the allyl group is roughly perpendicular to the mean plane of the 1,3-benzimidazol-2(3H)-one system, making a dihedral angle of 86.1 (2)°. In the crystal, each molecule is linked to its symmetry equivalent partner by a pair of N-H...O and C-H...O hydrogen bonds.

Related literature

For the pharmacological and biochemical properties of the title compound, see: Gravatt et al. (1994[Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338-4345.]); Horton et al. (2003[Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.]); Kim et al. (1996[Kim, J. S., Gatto, B., Yu, C., Liu, A., Liu, L. F. & La Voie, E. J. (1996). J. Med. Chem. 39, 992-998..]); Roth et al. (1997[Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199-4207.]). For compounds with similar structures, see: Belaziz et al. (2012[Belaziz, D., Kandri Rodi, Y., Essassi, E. M. & El Ammari, L. (2012). Acta Cryst. E68, o1276.]); Ouzidan et al. (2011[Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1822.]).

[Scheme 1]

Experimental

Crystal data
  • C10H10N2O

  • Mr = 174.20

  • Monoclinic, P 21 /c

  • a = 10.2749 (5) Å

  • b = 5.5787 (3) Å

  • c = 16.6220 (9) Å

  • [beta] = 100.976 (4)°

  • V = 935.35 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.38 × 0.29 × 0.27 mm

Data collection
  • Bruker X8 APEX diffractometer

  • 13429 measured reflections

  • 2570 independent reflections

  • 1393 reflections with I > 2[sigma](I)

  • Rint = 0.046

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.128

  • S = 1.04

  • 2570 reflections

  • 120 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.14 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H2...O1i 0.86 2.00 2.8274 (14) 161
C3-H3...O1ii 0.93 2.52 3.3080 (19) 142
Symmetry codes: (i) -x+1, -y, -z+2; (ii) [x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2005[Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). 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: FJ2602 ).


Acknowledgements

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

References

Belaziz, D., Kandri Rodi, Y., Essassi, E. M. & El Ammari, L. (2012). Acta Cryst. E68, o1276.  [CSD] [CrossRef] [details]
Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338-4345.  [CrossRef] [ChemPort] [PubMed] [ISI]
Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kim, J. S., Gatto, B., Yu, C., Liu, A., Liu, L. F. & La Voie, E. J. (1996). J. Med. Chem. 39, 992-998..  [CrossRef] [ChemPort] [PubMed] [ISI]
Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1822.  [CSD] [CrossRef] [details]
Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199-4207.  [ISI] [CrossRef] [ChemPort] [PubMed]
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]


Acta Cryst (2012). E68, o3212  [ doi:10.1107/S1600536812043620 ]

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.