Crystal structure of (3E)-3-[(4-nitrophenoxy)methyl]-4-phenylbut-3-en-2-one

Abstract

In the title compound, C17H15NO4, the conformation about the C=C double bond [1.348 (2) Å] is E with the ketone group almost co-planar [C—C—C—C torsion angle = 7.2 (2)°] but the phenyl group twisted away [C—C—C—C = 160.93 (17)°]. The terminal aromatic rings are almost perpendicular to each other [dihedral angle = 81.61 (9)°] giving the molecule an overall U-shape. The crystal packing feature benzene-C—H...O(ketone) contacts that lead to supramolecular helical chains along the b axis. These are connected by π–π interactions between benzene and phenyl rings [inter-centroid distance = 3.6648 (14) Å], resulting in the formation of a supramolecular layer in the bc plane.

Keywords

• crystal structure
• hydrogen bonding
• π–π interactions