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Volume 68 
Part 12 
Page o3370  
December 2012  

Received 14 October 2012
Accepted 8 November 2012
Online 17 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
R = 0.042
wR = 0.129
Data-to-parameter ratio = 17.5
Details
Open access

6-[4-Chloro-2-(trifluoromethyl)phenyl]-3-fluoro-2-methylpyridine

aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India,bDepartment of Studies and Research in Chemistry, U.C.S, Tumkur University, Tumkur, Karnataka 572 103, India,cDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, and dCentre of Advanced Study in Crystallography and Biophysics, University of Madras Guindy Campus, Chennai 600 025, India
Correspondence e-mail: drsreenivasa@yahoo.co.in

In the title compound, C13H8ClF4N, the dihedral angle between the benzene and pyridine rings is 59.8 (3)°. In the crystal, molecules are stacked in columns along the b axis through weak C-H...[pi] interactions.

Related literature

For the biological activity of pyridine derivatives, see: Patrick & Kinsmar (1996[Patrick, G. L. & Kinsmar, O. S. (1996). Eur. J. Med. Chem. 31, 615-624.]); Hishmat et al. (1990[Hishmat, O. H., Abdel Galil, F. M. & Farrag, D. S. (1990). Pharmazie, 45, 793-795.]); Doshi et al. (1999[Doshi, R., Kagthara, P. & Parekh, H. (1999). Indian J. Chem. 38, 348-352.]); Bhatt et al. (2001[Bhatt, A. H., Parekh, M. H., Parikh, K. A. & Parikh, A. R. (2001). J. Indian Chem. Soc. 40, 57-21.]).

[Scheme 1]

Experimental

Crystal data
  • C13H8ClF4N

  • Mr = 289.65

  • Monoclinic, P 21 /n

  • a = 13.1813 (7) Å

  • b = 4.5837 (3) Å

  • c = 20.4448 (11) Å

  • [beta] = 92.441 (3)°

  • V = 1234.14 (12) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.34 mm-1

  • T = 293 K

  • 0.2 × 0.18 × 0.16 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • 11077 measured reflections

  • 3033 independent reflections

  • 2116 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.042

  • wR(F2) = 0.129

  • S = 1.01

  • 3033 reflections

  • 173 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.23 e Å-3

  • [Delta][rho]min = -0.30 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C8-C12 ring.

D-H...A D-H H...A D...A D-H...A
C13-H13B...Cg1i 0.96 2.83 3.606 (2) 138
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 2004[Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: IS5209 ).


Acknowledgements

Authors thank Dr. S. C. Sharma, Vice Chancellor, Tumkur University, Tumkur for his constant encouragement and G·B. Sadananda, Department of Studies and Research in Physics, U.C.S. Tumkur University, Tumkur, for his help and valuable suggestions. BSP thanks Dr. H. C. Devaraje Gowda, Department of Physics, Yuvarajas College (constituent), University of Mysore for his guidance.

References

Bhatt, A. H., Parekh, M. H., Parikh, K. A. & Parikh, A. R. (2001). J. Indian Chem. Soc. 40, 57-21.
Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.
Doshi, R., Kagthara, P. & Parekh, H. (1999). Indian J. Chem. 38, 348-352.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Hishmat, O. H., Abdel Galil, F. M. & Farrag, D. S. (1990). Pharmazie, 45, 793-795.  [ChemPort] [PubMed]
Patrick, G. L. & Kinsmar, O. S. (1996). Eur. J. Med. Chem. 31, 615-624.  [CrossRef] [ChemPort] [ISI]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3370  [ doi:10.1107/S1600536812046211 ]

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