Crystal structure of 4-[(adamantan-1-yl)amino]naphthalene-1,2-dione

Abstract

The title compound, C20H21NO2, an example of a stable 1,2-naphthoquinone, was determined by single-crystal X-ray diffraction analysis at 100 K. This structure illustrates steric buttressing of the adamantanyl group, forcing the N—H group into the coplanar aromatic C—H. The presence of strong delocalization between the planar N atom at the 4-position and the carbonyl group at the 2-position is indicated. In the crystal, C—H...O and C—H...π interactions link the molecules into a three-dimensional network.

Keywords

• crystal structure
• adamantane
• N—H...O hydrogen bonding
• intramolecular hydrogen bonding
• naphthoquinone