(2E)-3-(4-Bromophenyl)-1-(2-methyl-4-phenyl-3-quinolyl)prop-2-en-1-one

The conformation about the ethene bond [1.316 (3) Å] in the title compound, C25H18BrNO, is E. The quinoline ring forms dihedral angles of 67.21 (10) and 71.68 (10)° with the benzene and bromo-substituted benzene rings, respectively. Highlighting the non-planar arrangement of aromatic rings, the dihedral angle formed between the benzene rings is 58.57 (12)°.

The conformation about the ethene bond [1.316 (3) Å ] in the title compound, C 25 H 18 BrNO, is E. The quinoline ring forms dihedral angles of 67.21 (10) and 71.68 (10) with the benzene and bromo-substituted benzene rings, respectively. Highlighting the non-planar arrangement of aromatic rings, the dihedral angle formed between the benzene rings is 58.57 (12) .

Experimental
VV is grateful to the DST-India for funding through the Young Scientist Scheme (Fast Track Proposal).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG2673).
In the structure of (I), the conformation about the C17═C18 [1.316 (3) Å] bond is E, Fig. 1. The chalcone residue is essentially planar as seen in the O1-C16-C17-C18 torsion angle of 173.7 (2) °. While the planarity extends out to the 4-bromobenzene ring [the C17-C18-C19-C20 torsion angle is -175.6 (2) °] this is not true for the quinoline residue (r.m.s. deviation = 0.0164 Å) which is twisted out of the plane through the chalcone residue: the C7-C8-C16-C17 torsion angle is 112.9 (2) °. In the same way, the C7-bound benzene ring is significantly twisted out of the plane of the quinoline ring as seen in the C6-C7-C10-C11 torsion angle of -67.0 (3) °. The non-planar nature of the molecule is reflected in the dihedral angles formed between the quinoline molecule and the benzene and bromo-substituted benzene rings of 67.21 (10) and 71.68 (10)°, respectively; the dihedral angle formed between the benzene rings is 58.57 (12) °.

Experimental
A mixture of 3-acetyl-2-methyl-4-phenylquinoline (2.6 g 0.01 M) and 4-bromobenzaldehyde (1.84 g 0.01 M), and a catalytic amount of KOH in distilled ethanol was stirred for about 12 h. The resulting mixture was concentrated to remove ethanol, poured onto ice, and neutralized with dilute acetic acid. The resultant solid was filtered, dried, purified by column chromatography using 1:1 mixture of ethyl acetate and petroleum ether, and recrystallized using ethyl acetate; yield: 65 % and m.pt: 459 K.
supplementary materials sup-2 Figures Fig. 1. The molecular structure of (I) showing the atom-labelling scheme and displacement ellipsoids at the 35% probability level.