2-[(1H-Imidazol-1-yl)meth­yl]-1-[4-(trifluoro­meth­yl)phen­yl]-1H-indole

Wang, R.; Shi, H.; Du, L.; Zhao, J.; Liu, J.

doi:10.1107/S1600536812010471

Volume 68
Part 4
Page o1081
April 2012

Received 1 March 2012
Accepted 9 March 2012
Online 17 March 2012

Key indicators
Single-crystal X-ray study
T = 100 K
Mean (C-C) = 0.004 Å
R = 0.079
wR = 0.214
Data-to-parameter ratio = 19.9
Details

2-[(1H-Imidazol-1-yl)methyl]-1-[4-(trifluoromethyl)phenyl]-1H-indole

Rui Wang,^a Hong-fan Shi,^a Lin Du,^a Jing-feng Zhao ^a and Jian-ping Liu ^a ^*

^aKey Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming 650091, People's Republic of China
Correspondence e-mail: jpliu@ynu.edu.cn

In the title compound, C₁₉H₁₄F₃N₃, the dihedral angles between the mean planes of the indole ring and the 4-CF₃-phenyl and imidazole rings are 54.95 (4) and 61.36 (7)°, respectively.

Related literature

For background to indole derivatives and their biological activity, see: Muftuoglua & Mustatab (2010); Jiao et al. (2010). For related structures, see: Borgne et al. (1999); Lézé et al. (2006); Marchand et al. (2003).

Experimental

Crystal data

C₁₉H₁₄F₃N₃
M_r = 341.33
Orthorhombic, P b c a
a = 10.3732 (17) Å
b = 7.9960 (13) Å
c = 37.665 (6) Å
V = 3124.0 (9) Å³
Z = 8
Mo K radiation
= 0.11 mm^-1
T = 100 K
0.53 × 0.26 × 0.05 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) T_min = 0.943, T_max = 0.994
30000 measured reflections
4505 independent reflections
3217 reflections with I > 2(I)
R_int = 0.093

Refinement

R[F² > 2(F²)] = 0.079
wR(F²) = 0.214
S = 0.99
4505 reflections
226 parameters
H-atom parameters constrained
_max = 0.51 e Å^-3
_min = -0.38 e Å^-3

Data collection: APEX2 (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2125 ).

Acknowledgements

This work was supported by the Natural Science Foundation of P. R. China (20562012).

References

Borgne, M. L., Marchand, P., Delevoye-Seiller, B., Robert, J.-M., Baut, G. L., Hartmann, R. W. & Palzer, M. (1999). Bioorg. Med. Chem. Lett. 9, 333-336.
Bruker (1998). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Jiao, J., Xiang, H. & Liao, Q. (2010). Curr. Med. Chem. 17, 3476-3487.
Lézé, M.-P., Borgne, M. L., Pinson, P., Palusczak, A., Duflos, M., Baut, G. L. & Hartmann, R. W. (2006). Bioorg. Med. Chem. Lett. 16, 1134-1137.
Marchand, P., Borgne, M. L., Palzer, M., Baut, G. L. & Hartmann, R. W. (2003). Bioorg. Med. Chem. Lett. 13, 1553-1555.
Muftuoglua, Y. & Mustatab, G. (2010). Bioorg. Med. Chem. Lett. 20, 3050-3064.
Sheldrick, G. M. (2004). SADBAS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds