1-Allyl-1H-1,3-benzimidazol-2(3H)-one

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

doi:10.1107/S1600536812043620

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 (C-C) = 0.002 Å
R = 0.045
wR = 0.128
Data-to-parameter ratio = 21.4
Details

1-Allyl-1H-1,3-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

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-HO and C-HO hydrogen bonds.

Related literature

For the pharmacological and biochemical properties of the title compound, see: Gravatt et al. (1994); Horton et al. (2003); Kim et al. (1996); Roth et al. (1997). For compounds with similar structures, see: Belaziz et al. (2012); Ouzidan et al. (2011).

Experimental

Crystal data

C₁₀H₁₀N₂O
M_r = 174.20
Monoclinic, P 2₁ /c
a = 10.2749 (5) Å
b = 5.5787 (3) Å
c = 16.6220 (9) Å
= 100.976 (4)°
V = 935.35 (8) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.046

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.128
S = 1.04
2570 reflections
120 parameters
H-atom parameters constrained
_max = 0.14 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N2-H2O1ⁱ	0.86	2.00	2.8274 (14)	161
C3-H3O1ⁱⁱ	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); cell refinement: SAINT (Bruker, 2005); 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: 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.
Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338-4345.
Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.
Kim, J. S., Gatto, B., Yu, C., Liu, A., Liu, L. F. & La Voie, E. J. (1996). J. Med. Chem. 39, 992-998..
Ouzidan, Y., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o1822.
Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199-4207.
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

1-Allyl-1H-1,3-benzimidazol-2(3H)-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Acknowledgements

References