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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 [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.091
Data-to-parameter ratio = 11.8
Details
Open access

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

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[Bock, V. D., Hiemstra, H. & van Maarseveen, J. H. (2006). Eur. J. Org. Chem. pp. 51-68.]); Irie et al. (2012[Irie, T., Fujii, I. & Sawa, M. (2012). Bioorg. Med. Chem. Lett. 22, 591-596.]). For biological background, see: Jia & Zhu (2010[Jia, Z. & Zhu, Q. (2010). Bioorg. Med. Chem. Lett. 20, 6222-6225.]); Henderson et al. (2012[Henderson, L. C., Altimari, J. M., Dyson, G., Servinis, L., Niranjan, B. & Risbridger, G. P. (2012). Bioorg. Chem. 40, 1-5.]); Alam et al. (2006[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.], 2007[Alam, M. S., Ozoe, F., Matsumura, F. & Ozoe, Y. (2007). Bioorg. Med. Chem. 15, 5090-5104.]). For related structures, see: Lin et al. (2008[Lin, J. R., Yao, J. Y. & Zhao, H. (2008). Acta Cryst. E64, o1843.]); Lin (2010[Lin, J. R. (2010). Acta Cryst. E66, o1967.]).

[Scheme 1]

Experimental

Crystal data
  • C15H9ClF3N3

  • Mr = 323.70

  • Monoclinic, C 2/c

  • a = 30.7475 (16) Å

  • b = 5.8877 (3) Å

  • c = 15.4364 (8) Å

  • [beta] = 105.470 (5)°

  • V = 2693.2 (2) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 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[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]), Tmin = 0.902, Tmax = 0.928

  • 3934 measured reflections

  • 2355 independent reflections

  • 1899 reflections with I > 2[sigma](I)

  • Rint = 0.021

Refinement
  • R[F2 > 2[sigma](F2)] = 0.041

  • wR(F2) = 0.091

  • S = 1.07

  • 2355 reflections

  • 199 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.18 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England.]); data reduction: CrysAlis PRO; program(s) used to solve structure: TEXSAN (Molecular Structure Corporation, 2001[Molecular Structure Corporation. (2001). TEXSAN for Windows. MSC, 9009 New Trails Drive, The Woodlands, TX 77381, USA.]) and SIR97 (Altomare et al., 1999[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.]); program(s) used to refine structure: TEXSAN and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


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.  [ISI] [CrossRef] [PubMed] [ChemPort]
Alam, M. S., Ozoe, F., Matsumura, F. & Ozoe, Y. (2007). Bioorg. Med. Chem. 15, 5090-5104.  [CrossRef] [PubMed] [ChemPort]
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.  [ISI] [CrossRef] [ChemPort] [details]
Bock, V. D., Hiemstra, H. & van Maarseveen, J. H. (2006). Eur. J. Org. Chem. pp. 51-68.  [CrossRef]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Henderson, L. C., Altimari, J. M., Dyson, G., Servinis, L., Niranjan, B. & Risbridger, G. P. (2012). Bioorg. Chem. 40, 1-5.  [CrossRef] [ChemPort] [PubMed]
Irie, T., Fujii, I. & Sawa, M. (2012). Bioorg. Med. Chem. Lett. 22, 591-596.  [CrossRef] [ChemPort] [PubMed]
Jia, Z. & Zhu, Q. (2010). Bioorg. Med. Chem. Lett. 20, 6222-6225.  [CrossRef] [ChemPort] [PubMed]
Lin, J. R. (2010). Acta Cryst. E66, o1967.  [CSD] [CrossRef] [details]
Lin, J. R., Yao, J. Y. & Zhao, H. (2008). Acta Cryst. E64, o1843.  [CSD] [CrossRef] [details]
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.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2012). E68, o3159  [ doi:10.1107/S1600536812042705 ]

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