[Journal logo]

Volume 69 
Part 6 
Page o818  
June 2013  

Received 2 March 2013
Accepted 25 April 2013
Online 4 May 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean [sigma](C-C) = 0.004 Å
R = 0.057
wR = 0.208
Data-to-parameter ratio = 12.5
Details
Open access

1,3-Bis(2-methylprop-2-enoyl)-1H-benzimidazol-2(3H)-one

aDepartment of Chemistry, University College of Engineering Panruti (A Constituent College of Anna University), Panruti 607 106, Tamilnadu, India, and bDepartment of Chemistry, IIT Madras, Chennai, TamilNadu, India
Correspondence e-mail: hari_ran@yahoo.com

The molecules of the title compound, C15H14N2O3, possesses crystallographically imposed twofold rotational symmetry, so the asymmetric unit contains one half-molecule. The fused-ring system deviates significantly from planarity; the planes of the five- and six-membered rings are twisted with respect to each other by 3.0 (1)°. In the crystal, weak C-H...O hydrogen bonds link molecules related by translation in [010] into chains.

Related literature

For applications of substituted benzimidazoles, see: Gravatt et al. (1994[Gravatt, G. L., Baguley, B. C., Wilson, W. R. & Denny, W. A. (1994). J. Med. Chem. 37, 4338-4345.]); Srikanth et al. (2011[Srikanth, L., Varunraj, V., Raghunandar, N. & Venkateshwerlu, L. (2011). Pharma Chem. 3, 172-193.]). For the crystal structures of related compounds, see: Ouzidan 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.]); Kandri Rodi et al. (2011[Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o3234.]).

[Scheme 1]

Experimental

Crystal data
  • C15H14N2O3

  • Mr = 270.28

  • Monoclinic, C 2/c

  • a = 16.6359 (9) Å

  • b = 8.8629 (5) Å

  • c = 9.6221 (4) Å

  • [beta] = 102.775 (2)°

  • V = 1383.59 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 298 K

  • 0.22 × 0.18 × 0.10 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.980, Tmax = 0.991

  • 4086 measured reflections

  • 1165 independent reflections

  • 1042 reflections with I > 2[sigma](I)

  • Rint = 0.014

Refinement
  • R[F2 > 2[sigma](F2)] = 0.057

  • wR(F2) = 0.208

  • S = 1.16

  • 1165 reflections

  • 93 parameters

  • 2 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.41 e Å-3

  • [Delta][rho]min = -0.36 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C1-H1...O1i 0.93 2.57 3.193 (3) 124
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). 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: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV5390 ).


Acknowledgements

The authors acknowledge the Department of Chemistry, IIT Madras, for the data collection.

References

Bruker (2004). 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]
Kandri Rodi, Y., Ouazzani Chahdi, F., Essassi, E. M., Luis, S. V., Bolte, M. & El Ammari, L. (2011). Acta Cryst. E67, o3234.  [CSD] [CrossRef] [details]
Ouzidan, Y., Kandri Rodi, Y., Jasinski, J. P., Butcher, R. J., Golen, J. A. & El Ammari, L. (2011). Acta Cryst. E67, o1091.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [details]
Srikanth, L., Varunraj, V., Raghunandar, N. & Venkateshwerlu, L. (2011). Pharma Chem. 3, 172-193.  [ChemPort]


Acta Cryst (2013). E69, o818  [ doi:10.1107/S1600536813011380 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.