1-(2-Isopropyl-4,7-dimethyl-3-nitronaphthalen-1-yl)ethanone

Abstract

The title compound, C17H19NO3, was synthesized in four steps from a mixture of α-, β- and γ-himachalene, which was isolated from an essential oil of the Atlas cedar (Cedrus Atlantica). The dihedral angle between the two rings of the naphthalene unit is 1.38 (9)°. The nitro group and the acetyl group lie almost normal to the mean plane of the naphthalene unit, making dihedral angles of 79.35 (16)° and 89.75 (17)°, respectively, and are inclined to one another by 52.9 (2)°. There is an intramolecular C—H...O hydrogen bond present involving a nitro O atom and the H atom of the methyl C atom of the isopropyl group, forming an S(7) ring motif. In the crystal, molecules are linked by pairs of C—H...π interactions, forming inversion dimers. There are no other significant intermolecular interactions present.