1-(Prop-2-yn­yl)-1H-benzimidazol-2(3H)-one

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

doi:10.1107/S160053681205088X

Volume 69
Part 1
Page o119
January 2013

Received 12 December 2012
Accepted 14 December 2012
Online 22 December 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.002 Å
R = 0.035
wR = 0.101
Data-to-parameter ratio = 17.5
Details

1-(Prop-2-ynyl)-1H-benzimidazol-2(3H)-one

Younès Ouzidan,^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 Nanomaterials 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: ouazzani_chahid@yahoo.fr

The benzimidazolone part of the title molecule, C₁₀H₈N₂O, is almost planar [r.m.s. deviation = 0.014 (1) Å] and the NCH₂C [triple bond] CH group forms a dihedral angle of 67.95 (6)° with its best plane. In the crystal, molecules form inversion dimers via pairs of N-HO hydrogen bonds. C-HO interactions connect the dimers, forming a two-dimensional polymeric network parallel to (100).

Related literature

For pharmacological and biochemical properties of benzimidazole dirivatives, see: Gravatt et al. (1994); Horton et al. (2003); Kim et al. (1996); Roth et al. (1997). For similar structures, see: Ouzidan, Kandri Rodi, Butcheret al. (2011); Ouzidan, Kandri Rodi, Fronczek et al. (2011); Ouzidan, Kandri Rodi, Jasinski et al. (2011); Belaziz et al. (2012).

Experimental

Crystal data

C₁₀H₈N₂O
M_r = 172.18
Monoclinic, P 2₁ /c
a = 4.5553 (6) Å
b = 18.001 (3) Å
c = 10.7488 (13) Å
= 93.645 (8)°
V = 879.6 (2) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.41 × 0.32 × 0.15 mm

Data collection

Bruker X8 APEXII diffractometer
10826 measured reflections
2080 independent reflections
1753 reflections with I > 2(I)
R_int = 0.020

Refinement

R[F² > 2(F²)] = 0.035
wR(F²) = 0.101
S = 1.05
2080 reflections
119 parameters
H-atom parameters constrained
_max = 0.16 e Å^-3
_min = -0.16 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
N1-H1O1ⁱ	0.95	1.88	2.8226 (12)	174
C10-H10O1ⁱⁱ	0.96	2.39	3.2541 (17)	149
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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: GK2546 ).

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.
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., Kandri Rodi, Y., Butcher, R. J., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o283.
Ouzidan, Y., Kandri Rodi, Y., Fronczek, F. R., Venkatraman, R., El Ammari, L. & Essassi, E. M. (2011). Acta Cryst. E67, o362-o363.
Ouzidan, Y., Kandri Rodi, Y., Jasinski, J. P., Butcher, R. J., Golen, J. A. & El Ammari, L. (2011). Acta Cryst. E67, o1091.
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