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

Jayamoorthy, K.; Mohandas, T.; Sakthivel, P.; Jayabharathi, J.

doi:10.1107/S1600536813000834

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.038
wR = 0.105
Data-to-parameter ratio = 11.3
Details

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

K. Jayamoorthy,^a T. Mohandas,^b P. Sakthivel ^c ^* and J. Jayabharathi ^a

^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-HF 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); Cross et al. (1995); Fu et al. (2011); Zhang et al. (2010). For bond lengths and angles in related structures, see: Yoon et al. (2011); Kassim et al. (2012).

Experimental

Crystal data

C₂₀H₁₃F₃N₂
M_r = 338.32
Triclinic, $[P \overline 1]$
a = 8.7179 (4) Å
b = 9.6796 (5) Å
c = 11.3612 (6) Å
= 67.654 (2)°
= 68.123 (2)°
= 85.013 (2)°
V = 821.20 (7) Å³
Z = 2
Mo K radiation
= 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) T_min = 0.960, T_max = 0.986
16592 measured reflections
2889 independent reflections
2338 reflections with I > 2(I)
R_int = 0.032

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.105
S = 1.03
2889 reflections
255 parameters
36 restraints
H-atom parameters constrained
_max = 0.15 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C17-H17F3ⁱ	0.93	2.54	3.429 (6)	160
Symmetry code: (i) x, y, z-1.

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); 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.
Cross, E. M., White, K. M., Moshrefzadeh, R. S. & Francis, C. V. (1995). Macromolecules, 28, 2526-2532.
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.
Kassim, K., Hashim, N. Z. N., Fadzil, A. H. & Yusof, M. S. M. (2012). Acta Cryst. E68, o799.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Yoon, Y. K., Ali, M. A., Choon, T. S., Hemamalini, M. & Fun, H.-K. (2011). Acta Cryst. E67, o1215.
Zhang, W., Chen, L. Z., Gou, M., Li, Y. H., Fu, D. W. & Xiong, R. G. (2010). Cryst. Growth Des. 10, 1025-1027.

organic compounds