[Journal logo]

Volume 69 
Part 2 
Page o238  
February 2013  

Received 4 January 2013
Accepted 7 January 2013
Online 16 January 2013

Key indicators
Single-crystal X-ray study
T = 150 K
Mean [sigma](C-C) = 0.003 Å
R = 0.041
wR = 0.103
Data-to-parameter ratio = 12.8
Details
Open access

2-(1H-Imidazol-1-yl)-4-[3-(trifluoromethyl)phenyl]-1,3-thiazole

aDepartment of Chemistry, M.V. Lomonosov Moscow State University, Leninskie Gory 1/3, Moscow 119991, Russian Federation,bInstitute of Physiologically Active Compounds, Russian Academy of Sciences, Chernogolovka 142432, Moscow Region, Russian Federation,cInstitute of General and Inorganic Chemistry, Russian Academy of Sciences, Leninskii prosp. 31, Moscow 119991, Russian Federation, and dSchool of Pharmacy, National Taiwan University, Taipei 100, Taiwan
Correspondence e-mail: kudr@org.chem.msu.ru

The title compound, C13H8F3N3S, consists of three linked aromatic rings. The whole molecule (except for the three F atoms) is planar to within 0.225 (2) Å. In the crystal, adjacent molecules are linked into chains along the ac diagonal by weak C-H...N interactions.

Related literature

For general background to the synthesis of imidazolothiazoles by copper-catalysed coupling, see: Zhu et al. (2007[Zhu, L., Guo, P., Li, G., Lan, J., Xie, R. & You, J. (2007). J. Org. Chem. 72, 8535-8538.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8F3N3S

  • Mr = 295.28

  • Monoclinic, P 21 /c

  • a = 8.4152 (7) Å

  • b = 19.2403 (15) Å

  • c = 8.4105 (7) Å

  • [beta] = 114.210 (1)°

  • V = 1241.98 (18) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.29 mm-1

  • T = 150 K

  • 0.40 × 0.20 × 0.10 mm

Data collection
  • Bruker SMART APEXII diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.893, Tmax = 0.972

  • 9797 measured reflections

  • 2716 independent reflections

  • 2164 reflections with I > 2[sigma](I)

  • Rint = 0.049

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

  • wR(F2) = 0.103

  • S = 1.07

  • 2716 reflections

  • 213 parameters

  • All H-atom parameters refined

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.27 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C9-H9...N3i 0.95 (2) 2.34 (2) 3.278 (2) 169.4 (18)
Symmetry code: (i) x+1, y, z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FF2095 ).


Acknowledgements

This study was partially supported by the Russian Foundation for Basic Research (project Nos. 11-03-00630_a and 12-03-92005-NSC_a) and by the National Science Council of the Republic of China (NSC101-2923-B-002-008-MY3).

References

Bruker (2008). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Zhu, L., Guo, P., Li, G., Lan, J., Xie, R. & You, J. (2007). J. Org. Chem. 72, 8535-8538.  [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o238  [ doi:10.1107/S1600536813000615 ]

This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.