(2E)-1-(2,4-Dichlorophenyl)-3-[4-(diethylamino)-2-hydroxyphenyl]prop-2-en-1-one

Abstract

In the title molecule, C19H19Cl2NO2, the angle between the mean planes of the 2,4-dichlorophenyl and 2-hydroxyphenyl groups is 81.8 (2)°. The ketone oxygen of the prop-2-en-1-one group is twisted in a synclinal conformation with the 2,4-dichlorophenyl group [torsion angle = −75.7 (2)°]. The two diethyl extensions from the 4-(diethylamino)-2-hydroxyphenyl group are twisted in anti- and syn-periplanar conformations. Crystal packing is stabilized by intermolecular C—H...O hydrogen bonding between the ketone O atom from the prop-2-en-1-one group and H atoms from both the 2-hydroxyphenyl ring and the hydroxy group; these hydrogen bonds link the molecules into chains along the diagonal of the bc face of the unit cell. The 2-hydroxyphenyl rings are stacked obliquely parallel to the ab face while the 2,4-dichlorophenyl rings are stacked obliquely parallel to the bc face of the unit cell, each in an inverted conformation. Additional intermolecular packing interactions occur between π orbitals of the 4-hydroxyphenyl ring and an H atom from a nearby 2,4-dichlorophenyl ring.