A Bis-Urea Naphthalene Macrocycle Displaying Two Crystal Structures with Parallel Ureas

Author(s)

Michael F. Geer, University of South Carolina - Columbia
Mark D. Smith, University of South Carolina - ColumbiaFollow
Linda S. Shimizu, University of South Carolina - ColumbiaFollow

Document Type

Article

Subject Area(s)

Chemistry

Abstract

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.

Digital Object Identifier (DOI)

https://doi.org/10.1039/C1CE05207A

Publication Info

Published in CrystEngComm, Volume 13, Issue 11, 2011, pages 3665-3669.

Rights

© CrystEngComm 2011, Royal Society of Chemistry.

APA Citation

Geer, M., Smith, M., & Shimizu, L. (2011). A Bis-Urea Naphthalene Macrocycle Displaying Two Crystal Structures with Parallel Ureas. CrystEngComm, 13(11), 3665–3669. https://doi.org/10.1039/C1CE05207A