[Journal logo]

Volume 69 
Part 2 
Page o264  
February 2013  

Received 3 January 2013
Accepted 12 January 2013
Online 19 January 2013

Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
Disorder in main residue
R = 0.064
wR = 0.157
Data-to-parameter ratio = 10.5
Details
Open access

2-[4-(Trifluoromethoxy)phenyl]-1H-benzimidazole

aDepartment of Studies in Chemistry, Bangalore University, Bangalore 560 001, India
Correspondence e-mail: noorsb@rediffmail.com

In the title compound, C14H9F3N2O, the best planes of the benzimidazole group and benzene ring form a dihedral angle of 26.68 (3)°. In the crystal, N-H...N hydrogen bonds link the molecules into infinite chains parallel to the c axis. Stacking interactions between the benzimidazole groups [centroid-centroid distance = 3.594 (5) Å] assemble the molecules into layers parallel to (100). The trifluoromethyl group is disordered over three sets of sites with site-occupancy factors of 0.787 (4), 0.107 (7) and 0.106 (7).

Related literature

For therapeutic and medicinal properties of benzimidazole derivatives, see: Chimirri et al. (1991[Chimirri, A., Grasso, S., Monforte, A. M., Monforte, P. & Zappala, M. (1991). Il Farmaco, 46, 925-933.]); Benavides et al. (1995[Benavides, J., Schoemaker, H., Dana, C., Clausture, Y., Delahaye, M., Prouteau, M., Manoury, P., Allen, J. V., Scatton, B., Langer, S. Z. & Arbilla, S. (1995). Arzneim. Forsch. (Drug. Res.), 45, 551-558.]); Ishihara et al. (1994[Ishihara, K., Ichikawa, T., Komuro, Y., Ohara, S. & Hotta, K. (1994). Arzneim. Forsch. (Drug. Res.), 44, 827-830.]); Kubo et al. (1993[Kubo, K., Kohara, Y., Imamia, E., Sugiura, Y., Inada, Y., Furukawa, Y., Nishikawa, K. & Naka, T. (1993). J. Med. Chem. 36, 2182-2195.]). For related structures, see: Jian et al. (2006[Jian, F.-F., Yu, H.-Q., Qiao, Y.-B., Zhao, P.-S. & Xiao, H.-L. (2006). Acta Cryst. E62, o5194-o5195.]); Rashid, Tahir, Yusof et al. (2007[Rashid, N., Tahir, M. K., Yusof, N. M. & Yamin, B. M. (2007). Acta Cryst. E63, o1260-o1261.]); Rashid, Tahir, Kanwal et al. (2007[Rashid, N., Tahir, M. K., Kanwal, S., Yusof, N. M. & Yamin, B. M. (2007). Acta Cryst. E63, o1402-o1403.]).

[Scheme 1]

Experimental

Crystal data
  • C14H9F3N2O

  • Mr = 278.23

  • Monoclinic, P 21 /c

  • a = 14.476 (6) Å

  • b = 9.312 (4) Å

  • c = 9.835 (4) Å

  • [beta] = 108.192 (8)°

  • V = 1259.5 (9) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.13 mm-1

  • T = 296 K

  • 0.18 × 0.16 × 0.16 mm

Data collection
  • Bruker SMART APEX CCD detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.978, Tmax = 0.980

  • 6284 measured reflections

  • 2209 independent reflections

  • 1333 reflections with I > 2[sigma](I)

  • Rint = 0.077

Refinement
  • R[F2 > 2[sigma](F2)] = 0.064

  • wR(F2) = 0.157

  • S = 1.00

  • 2209 reflections

  • 210 parameters

  • 21 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.26 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
N2-H21...N1i 0.86 2.07 2.864 (4) 154
Symmetry code: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}].

Data collection: SMART (Bruker, 1998[Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1998[Bruker. (1998). SMART, 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.]) and CAMERON (Watkin et al., 1996[Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GK2550 ).


Acknowledgements

NSB is thankful to the University Grants Commission (UGC), India, for financial assistance.

References

Benavides, J., Schoemaker, H., Dana, C., Clausture, Y., Delahaye, M., Prouteau, M., Manoury, P., Allen, J. V., Scatton, B., Langer, S. Z. & Arbilla, S. (1995). Arzneim. Forsch. (Drug. Res.), 45, 551-558.
Bruker. (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Chimirri, A., Grasso, S., Monforte, A. M., Monforte, P. & Zappala, M. (1991). Il Farmaco, 46, 925-933.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Ishihara, K., Ichikawa, T., Komuro, Y., Ohara, S. & Hotta, K. (1994). Arzneim. Forsch. (Drug. Res.), 44, 827-830.
Jian, F.-F., Yu, H.-Q., Qiao, Y.-B., Zhao, P.-S. & Xiao, H.-L. (2006). Acta Cryst. E62, o5194-o5195.  [CSD] [CrossRef] [details]
Kubo, K., Kohara, Y., Imamia, E., Sugiura, Y., Inada, Y., Furukawa, Y., Nishikawa, K. & Naka, T. (1993). J. Med. Chem. 36, 2182-2195.  [CrossRef] [ChemPort] [PubMed] [ISI]
Rashid, N., Tahir, M. K., Kanwal, S., Yusof, N. M. & Yamin, B. M. (2007). Acta Cryst. E63, o1402-o1403.  [CSD] [CrossRef] [details]
Rashid, N., Tahir, M. K., Yusof, N. M. & Yamin, B. M. (2007). Acta Cryst. E63, o1260-o1261.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Watkin, D. J., Prout, C. K. & Pearce, L. J. (1996). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.


Acta Cryst (2013). E69, o264  [ doi:10.1107/S1600536813001220 ]

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.