Solid State Structure and Hydrogen Bonding of Some Cyclic NH Carboximides

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 centrosymmetric dimers, and one has bonding between NH and a remote bridging ether oxygen. Halogen bonding was also detected in one case.

Automated summary

Thirteen new crystal structures of cyclic NH carboximides have been determined and compared based on their intermolecular hydrogen bonding patterns. The structures include a new cyclobutane-fused succinimide, seven new simple bi- and tricyclic succinimides derived from Diels-Alder reactions, three methylated glutarimides, a morpholinedione and adipimide, and the first seven-membered ring NH carboximide to be characterized. The compounds were found to adopt ribbon structures, centrosymmetric dimers, and bonding between NH and a remote bridging ether oxygen. Halogen bonding was also observed in one case.