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—HO and C—H interactions link the molecules into a three-dimensional network.