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Herein we synthesized a bis-urea macrocycle from 2,7-dimethylnaphthalene that displays an unusual parallel urea conformation. The naphthalenes also adopt a bowl shape over the anticipated parallel planar orientation. Crystallization of the macrocycle from different solvent systems affords two solvated forms. 1·DMSO·(H2O)2 has an extended columnar structure where parallel macrocycles are linked by intervening hydrogen bonded water molecules. In 1·(MeOH)2direct hydrogen-bonds link the macrocycles into chains, which hydrogen-bond with methanolmolecules to form a layered structure.

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Geer, M., Smith, M., & Shimizu, L. (2011). A Bis-Urea Naphthalene Macrocycle Displaying Two Crystal Structures with Parallel Ureas. CrystEngComm, 13(11), 3665–3669.