(E)-1-(2-Methyl-4-phenylquinolin-3-yl)-3-phenylprop-2-en-1-one

In the title compound, C25H19NO, the quinoline ring system is approximately planar, with a maximum deviation of 0.32 (1) Å, and forms dihedral angles of 80.74 (3) and 81.71 (4)° with the two phenyl rings. In the crystal. molecules are stacked along the b axis by way of a C—H⋯π interaction and a weak π–π interaction between the pyridine and phenyl rings with a centroid–centroid distance of 3.6924 (5) Å.

In the title compound, C 25 H 19 NO, the quinoline ring system is approximately planar, with a maximum deviation of 0.32 (1) Å , and forms dihedral angles of 80.74 (3) and 81.71 (4) with the two phenyl rings. In the crystal. molecules are stacked along the b axis by way of a C-HÁ Á Á interaction and a weakinteraction between the pyridine and phenyl rings with a centroid-centroid distance of 3.6924 (5) Å .
Cg3 is the centroid of the C20-C25 phenyl ring.

Comment
The quinolines and their derivatives are very important compounds because of their wide occurrence in natural products (Morimoto et al., 1991;Michael, 1997) and biologically active compounds (Markees et al., 1970;Campbell et al., 1988).
A large variety of quinolines have interesting physiological activities and found to have attractive applications as pharmaceuticals, agrochemicals and as synthetic building blocks (Maguire et al., 1994;Chen et al., 2001). The chalcones are open chain flavonoids, possessed a variety of biological activities, including antioxidant, anti-inflammation, antimicrobial, antiprotozoal, antiulcer, as well as other properties (Dimmock et al., 1999). In continuation of our interest in the synthesis of chalcone derivatives  In the title compound ( Fig. 1), the quinoline ring system (C7-C13/N1/C14/C15) is aproximately planar with a maximum deviation of 0.32 (1) Å at atom C15 and forms dihedral angles of 80.74 (3) and 81.71 (4)° with the C1-C6 and C20-C25 phenyl rings, respectively. Bond lengths (Allen et al., 1987) and angles are within the normal ranges.

Experimental
A mixture of 3-acetyl-2-methyl-4-phenylquinoline (2.6 g, 0.01 M) and benzaldehyde (1.06 g, 0.01 M) and a catalytic amount of KOH in 40 ml of distilled ethanol was stirred for about 12 h. The resulting mixture was concentrated to remove ethanol and then poured onto ice and neutralized with distilled acetic acid. The resultant solid was filtered, dried and purified by column chromatography using 1:1 mixture of ethylacetate and petroleum ether. Recrystallization was done in (8:4) petroleum ether, acetone mixture (m.p.: 422-423 K, yield: 82%).

Refinement
All H 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.   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 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.