Supramolecular architectures of simple aminoanthraquinones: Revised structure of 1-aminoanthraquinone

Abstract

The solid-state supramolecular architectures of 1-aminoanthraquinone and 1,5-diaminoanthraquinone were determined by single-crystal X-ray structural analysis. In this paper, revised model − in space group P2 1/ c − is given for the crystal structure of 1-aminanthraquinone. 1-Aminoantaquinone molecules are joined together in infinite chains by N H⋯O hydrogen bonds and stacked by face-to-face π−π and C H⋯π interactions thus creating layers and the characteristic herring-bone motif. In the structure of 1,5-diaminoanthraquinone the molecules are connected via N H⋯O hydrogen bonds in the 2D networks of (4,4) topology. These molecular networks are further stacked by face-to-face π−π and carbonyl−carbonyl interactions. The supramolecular organizations of these two compounds are compared with other simple aminoanthraquinones (with at least one non-substituted amino group) thus providing more insights into the basic principles of the solid-state assembling for this class of molecules.