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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 [sigma](C-C) = 0.002 Å
R = 0.035
wR = 0.101
Data-to-parameter ratio = 17.5
Details
Open access

1-(Prop-2-ynyl)-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 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-H...O hydrogen bonds. C-H...O 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[Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338-4345.]); Horton et al. (2003[Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.]); Kim et al. (1996[Kim, J. S., Gatto, B., Yu, C., Liu, A., Liu, L. F. & La Voie, E. J. (1996). J. Med. Chem. 39, 992-998.]); Roth et al. (1997[Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199-4207.]). For similar structures, see: Ouzidan, Kandri Rodi, Butcheret al. (2011[Ouzidan, Y., Kandri Rodi, Y., Butcher, R. J., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o283.]); Ouzidan, Kandri Rodi, Fronczek et al. (2011[Ouzidan, Y., Kandri Rodi, Y., Fronczek, F. R., Venkatraman, R., El Ammari, L. & Essassi, E. M. (2011). Acta Cryst. E67, o362-o363.]); Ouzidan, Kandri Rodi, Jasinski et al. (2011[Ouzidan, Y., Kandri Rodi, Y., Jasinski, J. P., Butcher, R. J., Golen, J. A. & El Ammari, L. (2011). Acta Cryst. E67, o1091.]); 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.]).

[Scheme 1]

Experimental

Crystal data
  • C10H8N2O

  • Mr = 172.18

  • Monoclinic, P 21 /c

  • a = 4.5553 (6) Å

  • b = 18.001 (3) Å

  • c = 10.7488 (13) Å

  • [beta] = 93.645 (8)°

  • V = 879.6 (2) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[sigma](I)

  • Rint = 0.020

Refinement
  • R[F2 > 2[sigma](F2)] = 0.035

  • wR(F2) = 0.101

  • S = 1.05

  • 2080 reflections

  • 119 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.16 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N1-H1...O1i 0.95 1.88 2.8226 (12) 174
C10-H10...O1ii 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[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: 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.  [CrossRef] [details]
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338-4345.  [CrossRef] [ChemPort] [PubMed] [ISI]
Horton, D. A., Bourne, G. T. & Smythe, M. L. (2003). Chem. Rev. 103, 893-930.  [ISI] [CrossRef] [PubMed] [ChemPort]
Kim, J. S., Gatto, B., Yu, C., Liu, A., Liu, L. F. & La Voie, E. J. (1996). J. Med. Chem. 39, 992-998.  [CrossRef] [ChemPort] [PubMed] [ISI]
Ouzidan, Y., Kandri Rodi, Y., Butcher, R. J., Essassi, E. M. & El Ammari, L. (2011). Acta Cryst. E67, o283.  [CSD] [CrossRef] [details]
Ouzidan, Y., Kandri Rodi, Y., Fronczek, F. R., Venkatraman, R., El Ammari, L. & Essassi, E. M. (2011). Acta Cryst. E67, o362-o363.  [CrossRef] [details]
Ouzidan, Y., Kandri Rodi, Y., Jasinski, J. P., Butcher, R. J., Golen, J. A. & El Ammari, L. (2011). Acta Cryst. E67, o1091.  [CrossRef] [details]
Roth, T., Morningstar, M. L., Boyer, P. L., Hughes, S. H., Buckheit, R. W. & Michejda, C. J. (1997). J. Med. Chem. 40, 4199-4207.  [ISI] [CrossRef] [ChemPort] [PubMed]
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, o119  [ doi:10.1107/S160053681205088X ]

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