1-(Prop-2-ynyl)-1H-benzimidazol-2(3H)- one Youne `s Ouzidan, a Youssef Kandri Rodi, a Fouad Ouazzani Chahdi, a * El Mokhtar Essassi, b,c Mohamed Saadi d and Lahcen El Ammari d a Laboratoire de Chimie Organique Applique ´e, Universite ´ Sidi Mohamed Ben Abdallah, Faculte ´ des Sciences et Techniques, Route d’immouzzer, BP 2202 Fe `s, Morocco, b Laboratoire de Chimie Organique He ´te ´rocyclique URAC21, Faculte ´ des Sciences, Universite ´ Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco, c Institute of Nanomaterials and Nanotechnology, MASCIR, Rabat, Morocco, and d Laboratoire de Chimie du Solide Applique ´e, Faculte ´ des Sciences, Universite ´ Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco Correspondence e-mail: ouazzani_chahid@yahoo.fr Received 12 December 2012; accepted 14 December 2012 Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.002 A ˚ ; R factor = 0.035; wR factor = 0.101; data-to-parameter ratio = 17.5. The benzimidazolone part of the title molecule, C 10 H 8 N 2 O, is almost planar [r.m.s. deviation = 0.014 (1) A ˚ ] and the NCH 2 C 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—HO hydrogen bonds. C—HO inter- actions connect the dimers, forming a two-dimensional polymeric network parallel to (100). Related literature For pharmacological and biochemical properties of benzimi- dazole 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 C 10 H 8 N 2 O M r = 172.18 Monoclinic, P2 1 =c a = 4.5553 (6) A ˚ b = 18.001 (3) A ˚ c = 10.7488 (13) A ˚  = 93.645 (8)  V = 879.6 (2) A ˚ 3 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[F 2 >2(F 2 )] = 0.035 wR(F 2 ) = 0.101 S = 1.05 2080 reflections 119 parameters H-atom parameters constrained Á max = 0.16 e A ˚ 3 Á min = 0.16 e A ˚ 3 Table 1 Hydrogen-bond geometry (A ˚ ,  ). D—HA D—H HA DA D—HA N1—H1O1 i 0.95 1.88 2.8226 (12) 174 C10—H10O1 ii 0.96 2.39 3.2541 (17) 149 Symmetry codes: (i) x þ 1; y þ 1; z þ 1; (ii) x; y þ 1 2 ; z þ 1 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). The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements. Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2546). 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 Acta Cryst. (2013). E69, o119 doi:10.1107/S160053681205088X Ouzidan et al. o119 Acta Crystallographica Section E Structure Reports Online ISSN 1600-5368