6-Chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline

In the title compound, C13H9ClF3N, the quinoline ring system makes a dihedral angle of 88.8 (2)° with the cyclopropyl ring.

In the title compound, C 13 H 9 ClF 3 N, the quinoline ring system makes a dihedral angle of 88.8 (2) with the cyclopropyl ring.
Thus, quinoline derivatives are good lead molecules to further develop drug candidates against mycobacterium tuberculosis and as antibacterial agents. On the basis of these observations, we have synthesized a quinoline derivative, with a cyclopropyl group and a trifluoromethyl group as substituents, expecting that the newly designed hybrid molecule would exhibit some antibacterial activity. In this paper we report the crystal structure of 6-chloro-2-cyclopropyl-4-(trifluoromethyl)quinoline.
The asymmetric unit of the 6-chloro-2-cyclopropyl-4-(trifluoromethyl) quinoline contains one molecule (Fig. 1). The quinoline ring system makes a dihedral angle of 88.8 (2)° with the cyclopropyl ring. Bond distances and bond angles in the quinoline ring system are in good agreement with those observed in related crystal structures (Skörska et al., 2005;Devarajegowda et al., 2010;Li et al., 2005). The packing of the molecules, when viewed along the b axis, is shown in Fig. 2.

Experimental
A mixture of cyclopropyl acetylene (0.012 mol), anhydrous zinc(II) (0.012 mol), triethylamine (1.67 ml, 0.012 mol), and toluene (25 ml) was stirred at 50°C for 2 h and cooled to 25°C. 4-Chloro-2-trifluoroacetylaniline (0.01 mol) was added and the reaction mixture was stirred at 25°C for 4 h, then at 50°C for 4 h. After cooling to room temperature, the mixture was added to water (10 ml) and extracted three times with ethyl acetate (20 ml). The combined organic phase was washed with brine and dried over anhydrous sodium sulfate. After removal of solvent, the residue was purified by column chromatography on silica gel (hexane/ethyl acetate; 20:1). M.p. 335 K.

Refinement
All H atoms were placed at calculated positions; C-H = 0.93 Å for aromatic H, C-H = 0.97 Å for methylene H; C-H = 0.98 Å for methine H. They were refined using a riding model with U iso (H) = 1.2U eq (C). Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen atoms are shown as spheres of arbitrary radius.   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 > 2σ(F 2 ) is used only for calculating Rfactors(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq Cl1 0.24504 (7