4-Chloro-3-methylphenyl quinoline-2-carboxylate

In the title compound, C17H12ClNO2, the dihedral angle between the mean planes of the quinoline ring system and the benzene ring is 68.7 (7)°. The mean plane of the carboxylate group is twisted from the latter planes by 14.0 (1) and 80.2 (4)°, respectively. In the crystal, weak C—H⋯O interactions are observed, forming chains along [001]. In addition, π–π stacking interactions [centroid–centroid distances = 3.8343 (13) and 3.7372 (13)Å] occur. No classical hydrogen bonds were observed.

In the title compound, C 17 H 12 ClNO 2 , the dihedral angle between the mean planes of the quinoline ring system and the benzene ring is 68.7 (7) . The mean plane of the carboxylate group is twisted from the latter planes by 14.0 (1) and 80.2 (4) , respectively. In the crystal, weak C-HÁ Á ÁO interactions are observed, forming chains along [001]. In addition, stacking interactions [centroid-centroid distances = 3.8343 (13) and 3.7372 (13)Å ] occur. No classical hydrogen bonds were observed.

Experimental
The title compound was prepared by the following procedure: To a mixture of 1.73 g (10 mmole) of quinaldic acid and 1.42 g (10 mmole) of 4-chloro-3-methylphenol in a round-bottomed flask fitted with a reflex condenser with a drying tube is added 0.75 g (5 mmole) of phosphorous oxychloride. The mixture is heated with occasional swirling, and temperature is maintained at 353-363 K. At the end of eight hours the reaction mixture is poured in to a solution of 2 g of sodium bicarbonate in 25 mL of water. The precipitated ester is collected on a filter and washed with water. The yield of crude, air dried 4-chloro-3-methyl phenyl quinoline-2-carboxylate is 1.89 to 2.05 g (60-70%). X-ray quality crystal was obtained by recrystallization from absolute ethanol (M.P.: 383-385 K).

Refinement
All H atoms were visible in a difference map, but placed in their calculated positions and then refined using the riding model with Atom-H lengths of 0.93Å (CH) or 0.96Å (CH 3 ). Isotropic displacement parameters for these atoms were set to 1.2 (CH) or 1.5 (CH 3 ) times U eq of the parent atom. Idealised Me refined as rotating group.

Figure 1
ORTEP drawing of the title compound showing the labeling scheme with 50% probability displacement ellipsoids.   Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

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