N-Methyl 2-Naphthyl Ketone: An X-Ray Diffraction and Density Functional Theory Study

Abstract

The crystallographically observed mol-ecular structure of the title compound, C19H17NO, and its inverted counterpart are compared with that calculated by density functional theory (DFT) at the B3LYP/6-311++G(d,p) level. The results from both methods suggest that the observed mol-ecular conformation of the title compound is primarily determined by inter-molecular inter-actions in the crystal structure. The periodic organization of the mol-ecules is stabilized by weak C - H⋯O and C - H⋯π hydrogen bonds and thus a two-dimensional puckered network consisting of R 4 4(22) and R 4 4(38) ring motifs is established. The title molecule has a (+)-antiperiplanar conformation about the C - C bond in the aminoacetone bridge. The pyramidal geometry observed around the vertex N atom is flattened by the presence of bulky phenyl and naphthylethanone fragments. © 2008 International Union of Crystallography.