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

Sreenivasa, S.; Manojkumar, K.E.; Suchetan, P.A.; Mohan, N.R.; Palakshamurthy, B.S.; Srinivasan, T.; Velmurgan, D.

doi:10.1107/S1600536812046211

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 (C-C) = 0.003 Å
R = 0.042
wR = 0.129
Data-to-parameter ratio = 17.5
Details

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

S. Sreenivasa,^a ^* K. E. Manojkumar,^a P. A. Suchetan,^b N. R. Mohan,^a B. S. Palakshamurthy,^c T. Srinivasan ^d and D. Velmurgan ^d

^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); Hishmat et al. (1990); Doshi et al. (1999); Bhatt et al. (2001).

Experimental

Crystal data

C₁₃H₈ClF₄N
M_r = 289.65
Monoclinic, P 2₁ /n
a = 13.1813 (7) Å
b = 4.5837 (3) Å
c = 20.4448 (11) Å
= 92.441 (3)°
V = 1234.14 (12) Å³
Z = 4
Mo K radiation
= 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(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.042
wR(F²) = 0.129
S = 1.01
3033 reflections
173 parameters
H-atom parameters constrained
_max = 0.23 e Å^-3
_min = -0.30 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

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

D-HA	D-H	HA	DA	D-HA
C13-H13BCg1ⁱ	0.96	2.83	3.606 (2)	138
Symmetry code: (i) x, y+1, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); 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.
Hishmat, O. H., Abdel Galil, F. M. & Farrag, D. S. (1990). Pharmazie, 45, 793-795.
Patrick, G. L. & Kinsmar, O. S. (1996). Eur. J. Med. Chem. 31, 615-624.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds