The 2,3-anhydro-α-cyclomannin−1-propanol hexahydrate: topography, lipophilicity pattern and solid-state architecture

Abstract

As evidenced by its X-ray structural analysis, 2,3-anhydro-α-cyclomannin 6, a cyclooligosaccharide consisting of six α-(1→4)-linked 2,3-anhydro -d-mannopyranose units, readily incorporates 1-propanol into its cavity such that hydrophobic and hydrophilic surface regions of guest and host match at their interfaces. Together with water, the macrocycle and its guest assemble into a unique solid-state architecture, featuring layers of head-to-head dimers of the macrocycle with its guest, separated by equally distinct layers of water molecules, which are engaged in an intense hydrogen bonding network with the 6-CH 2OH and the propanol-OH groups. The overall guest–host topography is thus reverse to that of the respective ethanol inclusion complex. 1