Solid state structure and hydrogen bonding of some cyclic NH carboximides

Abstract

Thirteen new crystal structures of cyclic NH carboximides have been determined and are compared with respect to the mode of intermolecular hydrogen bonding observed in the crystal. The structures include a new cyclobutane-fused succinimide, seven new simple bi- and tricyclic succinimides derived from Diels-Alder reactions of maleimide, three methylated glutarimides, a morpholinedione and adipimide, the first seven-membered ring NH carboximide to be structurally characterised. Overall seven of the compounds adopt a ribbon structure, five show centro-symmetric dimers, and one has bonding between NH and a remote bridging ether oxygen. Halogen bonding was also detected in one case.