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

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⋯π interactions.

In the title compound, C 13 H 8 ClF 4 N, 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-HÁ Á Á interactions.
Keeping in view of the biological importance of this class of compound, we synthesized the title compound to study its X-ray crystal structure.
In the title compound, the dihedral angle between the least square planes through the benzene ring and the pyridine ring is 59.8 (3)°. In the absence of hydrogen bonds, the structure is stabilized by a weak intermolecular C-H···π interaction (Table 1).
Experimental 2-Methyl-3-fluoropiridine-6-boromic acid (8.4 mmol) was taken in a mixture of dioxane (20 ml) and water (5 ml) at RT undernitrogen atmosphere. The reaction mixture was degassed with argon for 10 min, and K 2 CO 3 (23.1 mmol) and dichlorobis(triphenylphosphene)-palladium(II) (0.231 mmol) were added and again degassed for 10 min. 2-Bromo-5chlorobenzotrifluoride (7.7 mmol) was added and then reaction mixture was heated to 100 °C for 1 h (reaction was monitored by TLC), and the reaction mass was cooled to RT, diluted with ethyl acetate, filtered over celite, and washed with ethyl acetate. The filtrate was washed with water and brine, and the ethyl acetate layer was dried with anhydrous Na 2 SO 4 and concentrated. The crude product was purified by tritulating with petroleum ether. Single crystals of the title compound used for X-ray diffraction studies were obtained from slow evaporation of the solution of the compound in petroleum ether-ethyl acetate mixture (1:1).

Refinement
The H atoms were positioned with idealized geometry (C-H = 0.93-0.96 Å) using a riding model with U iso (H) = 1.2 or 1.5U eq (C).

Computing details
Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT-Plus (Bruker, 2004); data reduction: SAINT-Plus (Bruker, 2004); 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 (Sheldrick, 2008   Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.