1-[4-Chloro-3-(trifluoro­meth­yl)phen­yl]-4-phenyl-1H-1,2,3-triazole

Altimari, J.M.; Healy, P.C.; Henderson, L.C.

doi:10.1107/S1600536812042705

Volume 68
Part 11
Page o3159
November 2012

Received 11 October 2012
Accepted 12 October 2012
Online 20 October 2012

Key indicators
Single-crystal X-ray study
T = 249 K
Mean (C-C) = 0.003 Å
R = 0.041
wR = 0.091
Data-to-parameter ratio = 11.8
Details

1-[4-Chloro-3-(trifluoromethyl)phenyl]-4-phenyl-1H-1,2,3-triazole

Jarrad M. Altimari,^a Peter C. Healy ^b ^* and Luke C. Henderson ^c

^aSRC for Biotechnology, Chemistry and Systems Biology, Faculty of Science and Technology, Deakin University, Vic, 3216, Australia,^bQueensland Micro and Nanotechnology Centre, Griffith University, Brisbane 4111, Australia, and ^cInstitute for Frontier Materials, SRC for Biotechnology, Chemistry and Systems Biology, Faculty of Science and Technology, Deakin University, Vic, 3216, Australia
Correspondence e-mail: P.Healy@griffith.edu.au

In the title compound, C₁₅H₉ClF₃N₃, the phenyl and chloro-trifluoromethyl benzene rings are twisted with respect to the planar triazole group, making dihedral angles of 21.29 (12) and 32.19 (11)°, respectively. In the crystal, the molecules pack in a head-to-tail arrangement along the a axis with closest inter-centroid distances between the triazole rings of 3.7372 (12) Å.

Related literature

For background to the synthesis of N-aryl-1,2,3-triazoles, see: Bock et al. (2006); Irie et al. (2012). For biological background, see: Jia & Zhu (2010); Henderson et al. (2012); Alam et al. (2006, 2007). For related structures, see: Lin et al. (2008); Lin (2010).

Experimental

Crystal data

C₁₅H₉ClF₃N₃
M_r = 323.70
Monoclinic, C 2/c
a = 30.7475 (16) Å
b = 5.8877 (3) Å
c = 15.4364 (8) Å
= 105.470 (5)°
V = 2693.2 (2) Å³
Z = 8
Mo K radiation
= 0.32 mm^-1
T = 249 K
0.33 × 0.26 × 0.24 mm

Data collection

Oxford Diffraction GEMINI S Ultra diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012), T_min = 0.902, T_max = 0.928
3934 measured reflections
2355 independent reflections
1899 reflections with I > 2(I)
R_int = 0.021

Refinement

R[F² > 2(F²)] = 0.041
wR(F²) = 0.091
S = 1.07
2355 reflections
199 parameters
H-atom parameters constrained
_max = 0.18 e Å^-3
_min = -0.22 e Å^-3

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO; program(s) used to solve structure: TEXSAN (Molecular Structure Corporation, 2001) and SIR97 (Altomare et al., 1999); program(s) used to refine structure: TEXSAN and SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: TK5159 ).

Acknowledgements

We acknowledge support of this work by Griffith University, the Queensland University of Technology, the Strategic Research Center for Biotechnology, Chemistry and Systems Biology and the Institute for Frontier Materials Deakin University.

References

Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.
Alam, M. S., Kajiki, R., Hanatani, H., Kong, X., Ozoe, F., Matsui, Y., Matsumura, F. & Ozoe, Y. (2006). J. Agric. Food Chem. 54, 1361-1372.
Alam, M. S., Ozoe, F., Matsumura, F. & Ozoe, Y. (2007). Bioorg. Med. Chem. 15, 5090-5104.
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.
Bock, V. D., Hiemstra, H. & van Maarseveen, J. H. (2006). Eur. J. Org. Chem. pp. 51-68.
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Irie, T., Fujii, I. & Sawa, M. (2012). Bioorg. Med. Chem. Lett. 22, 591-596.
Jia, Z. & Zhu, Q. (2010). Bioorg. Med. Chem. Lett. 20, 6222-6225.
Lin, J. R. (2010). Acta Cryst. E66, o1967.
Lin, J. R., Yao, J. Y. & Zhao, H. (2008). Acta Cryst. E64, o1843.
Molecular Structure Corporation. (2001). TEXSAN for Windows. MSC, 9009 New Trails Drive, The Woodlands, TX 77381, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds