Polymorphs, Pseudopolymorphs, and Co-Crystals of Orcinol: Exploring the Structural Landscape with High Throughput Crystallography

Abstract

An extensive search of the structural landscape of orcinol, 5-methyl-1,3-dihydroxybenzene, has been carried out with high throughput techniques. Polymorphs, pseudopolymorphs (solvates), and co-crystals are described. Several packing modes driven by O–H···N hydrogen bonds were identified for the orcinol–N-base co-crystals and their hydrates. In these several structural variations, the OH group conformations in the orcinol molecule were found to depend on the choice of co-formers and the crystallization conditions employed. The structural landscape of a molecule is properly described by a sufficiently large number of related crystal structures, and high throughput crystallization followed by rapid structure determinations enables one to access these structures efficiently. Any understanding of this landscape would enable the crystal engineer to reasonably anticipate crystal structures of benzene-1,3-diol co-crystals with N-bases.