Robust R22(8) hydrogen bonded dimer for crystal engineering of glycoluril derivatives

Abstract

A series of glycoluril derivatives 1–3 were examined through crystallographic characterization to reveal a highly conserved amide⋯amide homosynthon, with intermolecular R²₂(8) hydrogen bonding interactions. As expected, the intermolecular hydrogen bonding interactions promoted the dimerization of the building blocks 1–3, even in the presence of competing pyridine rings and various solvent molecules. These robust dimer synthons were then connected to form a one-dimensional chain through C–H⋯O interactions and further extended to a two-dimensional layer by additional C–H⋯π interactions. This robust hydrogen bond motif was achieved without interference from competing intermolecular interactions and significant changes in the hydrocarbon core, and as such has much potential for application as a supramolecular synthon for solid-state design.