1-(6-Chloro-2-methyl-4-phenylquinolin-3-yl)-3-(3-methoxyphenyl)prop-2-en-1-one

In the title compound, C26H20ClNO2, the quinoline ring system is approximately planar with a maximum deviation of 0.028 (2) Å and forms a dihedral angle of 73.84 (5)° with the phenyl ring. Two neighbouring molecules are arranged into a centrosymmetric dimer through a pair of intermolecular C—H⋯Cl interactions. A pair of intermolecular C—H⋯O hydrogen bonds link two methoxyphenyl groups into another centrosymmetric dimer, generating an R 2 2(8) ring motif. The structure is further stabilized by C—H⋯π interactions.

In the title compound, C 26 H 20 ClNO 2 , the quinoline ring system is approximately planar with a maximum deviation of 0.028 (2) Å and forms a dihedral angle of 73.84 (5) with the phenyl ring. Two neighbouring molecules are arranged into a centrosymmetric dimer through a pair of intermolecular C-HÁ Á ÁCl interactions. A pair of intermolecular C-HÁ Á ÁO hydrogen bonds link two methoxyphenyl groups into another centrosymmetric dimer, generating an R 2 2 (8) ring motif. The structure is further stabilized by C-HÁ Á Á interactions.

Comment
The quinolines and their derivatives are very important compounds because of their wide occurrence in natural products (Michael, 1997) and biologically active compounds (Markees et al., 1970). A large variety of quinolines have interesting physiological activities and found attractive applications as pharmaceuticals, agrochemicals and as synthetic building blocks (Kalluraya & Sreenivasa, 1998;Chen et al., 2001). The chalcones are open-chain flavonoids, possessing a variety of biological activities, including antioxidant, anti-inflammation, antimicrobial, antiprotozoal, antiulcer, as well as other properties (Dimmock et al., 1999). Importantly, chalcones have shown several anticancer activities as inhibitors of cancer cell proliferation, carcinogenesis and metastasis (Zi & Simoneau, 2005).
In the title compound ( Fig. 1), the quinoline ring system (C1-C9/N1) is approximately planar with a maximum deviation of 0.036 (1) Å at atom C11. This mean plane of quinoline ring forms a dihedral angle of 73.84 (5)° with the phenyl ring (C19-C24). Bond lengths (Allen et al., 1987) and angles are within the normal range and are comparable to closely related structures Loh et al., 2009).

Experimental
To the solution of 3-acetyl-6-chloro-2-methyl-4-phenylquinoline (2.95 g, 0.01 M), 3-methoxybenzaldehyde (1.36 g, 0.01 M) and a catalytic amount of KOH in distilled ethanol was added and stirred for about 12 h. The resulting mixture was concentrated to remove the ethanol and then poured onto ice and neutralized with diluted acetic acid. The resultant solid was filtered, dried and purified by column chromatography using 1:1 mixture of ethylacetate and petroleum ether (m.p.

Refinement
All hydrogen atoms were positioned geometrically (C-H = 0.93 or 0.96 Å) and were refined using a riding model, with U iso (H) = 1.2 or 1.5U eq (C). A rotating group model was applied to the methyl groups.