Crystal structure of the supramolecular linear polymer formed by the self-assembly of mono-6-deoxy-6-adamantylamide-β-cyclodextrin

• Published in: Acta crystallographica. Section B, Structural science Vol. 60; no. 2; pp. 204 - 210
• Main Authors: Tellini, Victor Hugo Soto, Jover, Aida, Galantini, Luciano, Meijide, Francisco, Tato, José Vázquez
• Format: Journal Article
• Language: English
• Published: 5 Abbey Square, Chester, Cheshire CH1 2HU, England Munksgaard International Publishers 01.04.2004; Blackwell
• Subjects: Amantadine - analogs & derivatives; Amantadine - chemistry; beta-Cyclodextrins - chemistry; Biological compounds; Condensed matter: structure, mechanical and thermal properties; Crystallography, X-Ray; Exact sciences and technology; Glucose - chemistry; Heterocyclic compounds; Hydrogen Bonding; Molecular Conformation; Molecular Structure; mono-6-deoxy-6-adamantylamide-β-cyclodextrin; Organic compounds; Physics; polymers; Polymers - chemistry; self-assembly; Structure of solids and liquids; crystallography; Structure of specific crystalline solids; supramolecular structures; Water - chemistry; Self-assembly; Cyclodextrin; Formamide; Adamantane; Hydrogen bonds; Orthorhombic lattices; Experimental study; Organic compounds; Macrocycle; Crystal structure
• ISSN: 0108-7681; 1600-5740
• DOI: 10.1107/S0108768104003775

Mono‐6‐deoxy‐6‐adamantylamide‐β‐cyclodextrin–dimethyl­form­amide–15H2O, C53H85NO35·C3H7NO·15H2O, crystallizes in the orthorhombic space group P212121. The adamantyl group is inserted into the cyclodextrin cavity of the adjacent molecule, entering by the side of the secondary hydroxy rim, thus forming a supramolecular linear polymer by self‐assembly. Adjacent macrocycles are linked into columns by hydrogen bonds involving the nearest glucose residues, and the structure is further stabilized by their involvement in hydrogen bonding with water molecules which reside in channels surrounding the polymer columns, thus acting as bridges between the cyclodextrin units. The centroid of the adamantyl group lies below the plane formed by the seven glycosidic O atoms of the host cyclodextrin, excluding water molecules from the secondary side of β‐cyclodextrin (β‐CD). Between the adamantyl group and the primary hydroxy rim of the cyclodextrin cavity lies a dimethylformamide molecule, which shields the hydrophobic adamantyl group from the primary hydroxy rim of its carrying β‐CD and excludes water molecules from the primary side of the β‐CD cavity.