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Volume 69 
Part 2 
Page o244  
February 2013  

Received 5 January 2013
Accepted 9 January 2013
Online 16 January 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.038
wR = 0.105
Data-to-parameter ratio = 11.3
Details
Open access

1-Phenyl-2-[4-(trifluoromethyl)phenyl]-1H-benzimidazole

aAnnamalai University, Chidambaram, Tamilnadu, India,bShri Angalamman College of Engineering And Technology, Siruganoor, Tiruchirappalli, Tamilnadu 621 105, India, and cUrumu Dhanalakshmi College, Tiruchirappalli, Tamilnadu 620 019, India
Correspondence e-mail: sakthi2udc@yahoo.com

In the title molecule, C20H13F3N2, the benzimidazole unit is close to being planar [maximum deviation = 0.012 (1) Å] and forms dihedral angles of 31.43 (7) and 61.45 (9)° with the 4-(trifluoromethyl)phenyl and 1-phenyl rings, respectively; the dihedral angle between these rings is 60.94 (10)°. In the crystal, C-H...F hydrogen bonds link the molecules into chains along the c-axis direction. The CF3 group is rotationally disordered with an occupancy ratio of 0.557 (8):0.443 (8) for the F atoms.

Related literature

For the properties of related compounds, see: Bu et al. (1996[Bu, X. R., Li, H., Derveer, D. V. & Mintz, E. A. (1996). Tetrahedron Lett. 37, 7331-7334.]); Cross et al. (1995[Cross, E. M., White, K. M., Moshrefzadeh, R. S. & Francis, C. V. (1995). Macromolecules, 28, 2526-2532.]); Fu et al. (2011[Fu, D. W., Zhang, W., Cai, H. L., Zhang, Y., Ge, J. Z., Xiong, R. G. & Huang, S. P. (2011). J. Am. Chem. Soc. 133, 12780-12786.]); Zhang et al. (2010[Zhang, W., Chen, L. Z., Gou, M., Li, Y. H., Fu, D. W. & Xiong, R. G. (2010). Cryst. Growth Des. 10, 1025-1027.]). For bond lengths and angles in related structures, see: Yoon et al. (2011[Yoon, Y. K., Ali, M. A., Choon, T. S., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o1215.]); Kassim et al. (2012[Kassim, K., Hashim, N. Z. N., Fadzil, A. H. & Yusof, M. S. M. (2012). Acta Cryst. E68, o799.]).

[Scheme 1]

Experimental

Crystal data
  • C20H13F3N2

  • Mr = 338.32

  • Triclinic, [P \overline 1]

  • a = 8.7179 (4) Å

  • b = 9.6796 (5) Å

  • c = 11.3612 (6) Å

  • [alpha] = 67.654 (2)°

  • [beta] = 68.123 (2)°

  • [gamma] = 85.013 (2)°

  • V = 821.20 (7) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 0.11 mm-1

  • T = 293 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker,2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.960, Tmax = 0.986

  • 16592 measured reflections

  • 2889 independent reflections

  • 2338 reflections with I > 2[sigma](I)

  • Rint = 0.032

Refinement
  • R[F2 > 2[sigma](F2)] = 0.038

  • wR(F2) = 0.105

  • S = 1.03

  • 2889 reflections

  • 255 parameters

  • 36 restraints

  • H-atom parameters constrained

  • [Delta][rho]max = 0.15 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C17-H17...F3i 0.93 2.54 3.429 (6) 160
Symmetry code: (i) x, y, z-1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: PLATON.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BV2218 ).


References

Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Bu, X. R., Li, H., Derveer, D. V. & Mintz, E. A. (1996). Tetrahedron Lett. 37, 7331-7334.  [CrossRef] [ChemPort] [ISI]
Cross, E. M., White, K. M., Moshrefzadeh, R. S. & Francis, C. V. (1995). Macromolecules, 28, 2526-2532.  [CrossRef] [ChemPort] [ISI]
Fu, D. W., Zhang, W., Cai, H. L., Zhang, Y., Ge, J. Z., Xiong, R. G. & Huang, S. P. (2011). J. Am. Chem. Soc. 133, 12780-12786.  [ISI] [CSD] [CrossRef] [ChemPort] [PubMed]
Kassim, K., Hashim, N. Z. N., Fadzil, A. H. & Yusof, M. S. M. (2012). Acta Cryst. E68, o799.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Yoon, Y. K., Ali, M. A., Choon, T. S., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o1215.  [CSD] [CrossRef] [details]
Zhang, W., Chen, L. Z., Gou, M., Li, Y. H., Fu, D. W. & Xiong, R. G. (2010). Cryst. Growth Des. 10, 1025-1027.  [CSD] [CrossRef] [ChemPort]


Acta Cryst (2013). E69, o244  [ doi:10.1107/S1600536813000834 ]

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