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Volume 69 
Part 9 
Pages o1477-o1478  
September 2013  

Received 5 August 2013
Accepted 21 August 2013
Online 31 August 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.003 Å
R = 0.047
wR = 0.141
Data-to-parameter ratio = 19.3
Details
Open access

1-Allyl-3-benzyl-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,bUnité de Catalyse et de Chimie du Solide (UCCS), UMR 8181, Ecole Nationale Supérieure de Chimie de Lille, France,cUSR 3290 Miniaturisation pour l'Analyse, la Synthèse et la Protéomique, 59655 Villeneuve d'Ascq Cedex, Université Lille 1, France,dLaboratoire de Chimie Organique Hétérocyclique, URAC 21, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue, Ibn Batouta, Rabat, Morocco, and eLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
Correspondence e-mail: amal_haoudi@yahoo.fr

In the title compound, C17H16N2O, the fused benzimidazol-2(3H)-one system is essentially planar, the largest deviation from the mean plane being 0.006 (2) Å for the carbonyl C atom. Its mean plane is almost perpendicular to the benzyl plane and to the allyl group, making dihedral angles of 80.6 (1) and 77.4 (3)°, respectively. The benzyl group and the allyl subsituent lie on opposite sides of the fused ring system. In the crystal, molecules are linked by bifurcated C-H...O hydrogen bonds in which the carbonyl O atom acts as accepter to two aromatic C-H groups, forming a two-dimensional network parallel to (001).

Related literature

For the biological activity of benzimidazole derivatives, see: Gravatt et al. (1994[Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338-4345.]); Soderlind et al. (1999[Soderlind, K. J., Gorodetsky, B., Singh, A. K., Bachur, N. R., Miller, G. G. & Lown, J. W. (1999). Anticancer Drug Des. 14, 19-36.]); Bouwman et al. (1990[Bouwman, E., Driessen, W. L. & Reedjik, J. (1990). Coord. Chem. Rev. 104, 143-172.]) and for potential applications in the treatment of some diseases, see: Zhu et al. (2008[Zhu, G.-D., Gandhi, V. B., Gong, J., Thomas, S., Luo, Y., Liu, X., Shi, Y., Klinghofer, V., Johnson, E. F., Frost, D., Donawho, C., Jarvis, K., Bouska, J., Marsh, K. C., Rosenberg, S. H., Giranda, V. L. & Penning, T. D. (2008). Bioorg. Med. Chem. Lett. 18, 3955-3958.]); Ogino et al. (2008[Ogino, Y., Ohtake, N., Nagae, Y., Matsuda, K., Moriya, M., Suga, T., Ishikawa, M., Kanesaka, M., Mitobe, Y., Ito, J., Kanno, T., Ishiara, A., Iwaasa, H., Ohe, T., Kanatani, A. & Fukami, T. (2008). Bioorg. Med. Chem. Lett. 18, 5010-5014.]); Shah et al. (2008[Shah, D. I., Sharma, M., Bansal, Y., Bansal, G. & Singh, M. (2008). Eur. J. Med. Chem. 43, 1808-1812.]). For their use as intermediates in chemical synthesis, see: Bai et al. (2001[Bai, Y., Lu, J., Shi, Z. & Yang, B. (2001). Synlett, 12, 544-546.]). For similar compounds, see: 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.], 2013[Belaziz, D., Kandri Rodi, Y., Kandri Rodi, A., Essassi, E. M., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o641-o642.]).

[Scheme 1]

Experimental

Crystal data
  • C17H16N2O

  • Mr = 264.32

  • Triclinic, [P \overline 1]

  • a = 9.0667 (2) Å

  • b = 9.3922 (2) Å

  • c = 9.6486 (2) Å

  • [alpha] = 94.218 (1)°

  • [beta] = 113.543 (1)°

  • [gamma] = 106.265 (1)°

  • V = 706.87 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.08 mm-1

  • T = 296 K

  • 0.43 × 0.20 × 0.16 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.967, Tmax = 0.988

  • 12670 measured reflections

  • 3494 independent reflections

  • 2573 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.047

  • wR(F2) = 0.141

  • S = 1.06

  • 3494 reflections

  • 181 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.15 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O1i 0.93 2.48 3.405 (2) 173
C14-H14...O1ii 0.93 2.56 3.330 (2) 141
Symmetry codes: (i) x-1, y, z; (ii) x, y+1, z.

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2009[Bruker (2009). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; 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: IM2438 ).


References

Bai, Y., Lu, J., Shi, Z. & Yang, B. (2001). Synlett, 12, 544-546.
Belaziz, D., Kandri Rodi, Y., Kandri Rodi, A., Essassi, E. M., Saadi, M. & El Ammari, L. (2013). Acta Cryst. E69, o641-o642.  [CrossRef] [ChemPort] [details]
Belaziz, D., Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Saadi, M. & El Ammari, L. (2012). Acta Cryst. E68, o3212.  [CSD] [CrossRef] [details]
Bouwman, E., Driessen, W. L. & Reedjik, J. (1990). Coord. Chem. Rev. 104, 143-172.  [CrossRef] [ChemPort] [ISI]
Bruker (2009). APEX2, SAINT-Plus and SADABS. 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]
Ogino, Y., Ohtake, N., Nagae, Y., Matsuda, K., Moriya, M., Suga, T., Ishikawa, M., Kanesaka, M., Mitobe, Y., Ito, J., Kanno, T., Ishiara, A., Iwaasa, H., Ohe, T., Kanatani, A. & Fukami, T. (2008). Bioorg. Med. Chem. Lett. 18, 5010-5014.  [CrossRef] [PubMed] [ChemPort]
Shah, D. I., Sharma, M., Bansal, Y., Bansal, G. & Singh, M. (2008). Eur. J. Med. Chem. 43, 1808-1812.  [CrossRef] [PubMed] [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Soderlind, K. J., Gorodetsky, B., Singh, A. K., Bachur, N. R., Miller, G. G. & Lown, J. W. (1999). Anticancer Drug Des. 14, 19-36.  [PubMed] [ChemPort]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [ChemPort] [details]
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.  [ISI] [CrossRef] [ChemPort] [details]
Zhu, G.-D., Gandhi, V. B., Gong, J., Thomas, S., Luo, Y., Liu, X., Shi, Y., Klinghofer, V., Johnson, E. F., Frost, D., Donawho, C., Jarvis, K., Bouska, J., Marsh, K. C., Rosenberg, S. H., Giranda, V. L. & Penning, T. D. (2008). Bioorg. Med. Chem. Lett. 18, 3955-3958.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o1477-o1478   [ doi:10.1107/S1600536813023568 ]

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