6-Methyl-1-(nitromethyl)-4-(propan-2-yl)naphthalene

Abstract

The title compound, C15H17NO2, was synthesized in two steps from a mixture of α-himachalene (2-methylene-6,6,9-trimethylbicyclo[5.4.01,7]undec-8-ene), β-himachalene (2,6,6,9-tetramethylbicyclo[5.4.01,7]undeca-1,8-diene) and γ-himachalene (2,6,6,9-tetramethylbicyclo[5.4.01,7]undeca-2,8-diene), which was isolated from an essential oil of the Atlas cedar (Cedrus atlantica). The nitro group and the isopropyl group lie almost normal to the mean plane of the naphthalene moiety, making dihedral angles of 83.13 (19) and 71.72 (16)°, respectively, and are inclined to one another by 49.8 (2)°. In the crystal, molecules are linked by pairs of C—H...π interactions and weak C—H...O interactions.

Keywords

• crystal structure
• α-β-and γ-himachalene
• Atlas cedar
• C—H...π interactions