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Volume 69 
Part 1 
Page o122  
January 2013  

Received 12 December 2012
Accepted 13 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.002 Å
R = 0.044
wR = 0.122
Data-to-parameter ratio = 19.6
Details
Open access

1-(4-Methylbenzyl)-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,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

In the title compound, C15H14N2O, the fused five- and six-membered ring system is essentially planar, the maximum deviation from the mean plane being 0.009 (1) Å. The benzimidazol-2(3H)-one residue is nearly perpendicular to the benzyl ring, forming a dihedral angle of 77.41 (6)°. In the crystal, inversion dimers are formed by pairs of N-H...O hydrogen bonds; these dimers are linked by weak C-H...O interactions into a two-dimensional array in the (102) plane.

Related literature

For pharmacological and biochemical properties of benzimidazole derivatives, see: Lee et al. (2004[Lee, Y. H. & Pavlostathis, S. G. (2004). Water Res. 38, 1838-1852.]); Deligeorgiev et al. (2011[Deligeorgiev, T., Kaloyanova, S. & Vasilev, S. (2011). Dyes Pigm. 90, 170-1276.]); Scott et al. (2002[Scott, L. J., Dunn, C. J., Mallarkey, G. & Sharpe, M. (2002). Drugs, 62, 1503-1538.]); Gothelf et al. (1998[Gothelf, K. V. & Jørgensen, K. A. (1998). Chem. Rev. 98, 863-909.]). For related structures, see: Belaziz et al. (2012[Belaziz, D., Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Saadi, M. & El Ammari, L. (2012). Acta Cryst. E68, o3212.]); 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
  • C15H14N2O

  • Mr = 238.28

  • Monoclinic, P 21 /n

  • a = 12.5585 (5) Å

  • b = 5.7181 (2) Å

  • c = 17.4153 (7) Å

  • [beta] = 95.277 (2)°

  • V = 1245.31 (8) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.51 × 0.42 × 0.15 mm

Data collection
  • Bruker X8 APEXII diffractometer

  • 16486 measured reflections

  • 3211 independent reflections

  • 2157 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.044

  • wR(F2) = 0.122

  • S = 1.02

  • 3211 reflections

  • 164 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.17 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
N1-H1N1...O1i 0.94 1.91 2.8317 (15) 166
C15-H15C...O1ii 0.96 2.58 3.514 (2) 165
C8-H8A...O1iii 0.97 2.61 3.5504 (18) 164
Symmetry codes: (i) -x+1, -y+2, -z; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]; (iii) x, y-1, z.

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: TK5182 ).


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., Ouazzani Chahdi, F., Essassi, E. M., Saadi, M. & El Ammari, L. (2012). Acta Cryst. E68, o3212.  [CrossRef] [details]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deligeorgiev, T., Kaloyanova, S. & Vasilev, S. (2011). Dyes Pigm. 90, 170-1276.  [CrossRef] [ChemPort]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gothelf, K. V. & Jørgensen, K. A. (1998). Chem. Rev. 98, 863-909.  [ISI] [CrossRef] [PubMed] [ChemPort]
Lee, Y. H. & Pavlostathis, S. G. (2004). Water Res. 38, 1838-1852.  [CrossRef] [PubMed] [ChemPort]
Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1822.  [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]


Acta Cryst (2013). E69, o122  [ doi:10.1107/S1600536812050726 ]

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