Crystal structure of (E)-1-(1-hydroxynaphthalen-2-yl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one

Abstract

The title compound, C22H20O5, is composed of a hydroxynaphthyl ring and a trimethoxyphenyl ring [the planes of which are inclined to one another by 21.61 (10)°] bridged by an unsaturated prop-2-en-1-one group. The mean plane of the prop-2-en-1-one group [–C(=O)—C=C–] is inclined to that of the naphthyl system and benzene rings by 3.77 (14) and 18.01 (16)°, respectively. There is an intramolecular O—H...O hydrogen bond present forming an S(6) ring motif. In the crystal, inversion-related molecules are linked by a slipped-parallel π–π interaction [intercentroid distance = 3.8942 (13) Å, interplanar distance = 3.478 (9) Å and slippage = 1.751 Å], and stack along the [101] direction. There are no other significant intermolecular interactions present.

Keywords

• crystal structure
• chalcones
• hydroxynaphthalene
• O—H...O hydrogen bond
• S(6) ring motif
• π–π slipped parallel interaction