1-(4-Methyl­benz­yl)-1H-benzimidazol-2(3H)-one

Belaziz, D.; Kandri Rodi, Y.; Ouazzani Chahdi, F.; Essassi, E.M.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536812050726

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 (C-C) = 0.002 Å
R = 0.044
wR = 0.122
Data-to-parameter ratio = 19.6
Details

1-(4-Methylbenzyl)-1H-benzimidazol-2(3H)-one

Dounia Belaziz,^a ^* Youssef Kandri Rodi,^a Fouad Ouazzani Chahdi,^a El Mokhtar Essassi,^b,^c Mohamed Saadi ^d and Lahcen El Ammari ^d

^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-HO hydrogen bonds; these dimers are linked by weak C-HO 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); Deligeorgiev et al. (2011); Scott et al. (2002); Gothelf et al. (1998). For related structures, see: Belaziz et al. (2012); Ouzidan et al. (2011).

Experimental

Crystal data

C₁₅H₁₄N₂O
M_r = 238.28
Monoclinic, P 2₁ /n
a = 12.5585 (5) Å
b = 5.7181 (2) Å
c = 17.4153 (7) Å
= 95.277 (2)°
V = 1245.31 (8) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.029

Refinement

R[F² > 2(F²)] = 0.044
wR(F²) = 0.122
S = 1.02
3211 reflections
164 parameters
H-atom parameters constrained
_max = 0.17 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1N1O1ⁱ	0.94	1.91	2.8317 (15)	166
C15-H15CO1ⁱⁱ	0.96	2.58	3.514 (2)	165
C8-H8AO1ⁱⁱⁱ	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); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip,2010).

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.
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Deligeorgiev, T., Kaloyanova, S. & Vasilev, S. (2011). Dyes Pigm. 90, 170-1276.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gothelf, K. V. & Jørgensen, K. A. (1998). Chem. Rev. 98, 863-909.
Lee, Y. H. & Pavlostathis, S. G. (2004). Water Res. 38, 1838-1852.
Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1822.
Scott, L. J., Dunn, C. J., Mallarkey, G. & Sharpe, M. (2002). Drugs, 62, 1503-1538.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.

organic compounds