The crystal structure of the 1:1 inclusion complex of β-cyclodextrin with squaric acid

The crystal and molecular structure of the 1:1 inclusion complex of β-cyclodextrin (cyclomaltoheptaose) with squaric acid (3,4-dihydroxycyclobutene-1,2-dione) was determined by X-ray diffraction. The complex crystallizes in the monoclinic P2 1 space group and belongs to the monomeric cage-type, char...

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Bibliographic Details
Published inCarbohydrate research Vol. 333; no. 2; pp. 145 - 151
Main Authors Crisma, Marco, Fornasier, Roberto, Marcuzzi, Franco
Format Journal Article
LanguageEnglish
Published Netherlands Elsevier Ltd 03.07.2001
Subjects
beta-Cyclodextrins
Carbohydrate Conformation
Crystal structure
Crystallography, X-Ray
Cyclobutanes - chemistry
Cyclodextrins - chemistry
Hydrogen Bonding
Inclusion complex
Models, Molecular
Squaric acid
β-Cyclodextrin
β-Cyclodextrin
Squaric acid
Inclusion complex
Crystal structure
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Summary:The crystal and molecular structure of the 1:1 inclusion complex of β-cyclodextrin (cyclomaltoheptaose) with squaric acid (3,4-dihydroxycyclobutene-1,2-dione) was determined by X-ray diffraction. The complex crystallizes in the monoclinic P2 1 space group and belongs to the monomeric cage-type, characterized by a herringbone-like packing motif. Co-crystallized water molecules are present on seven sites, of which six are fully occupied. The guest molecule is placed inside the β-cyclodextrin cavity, perpendicular to the plane defined by the glycosidic O-4 n atoms, and held in place by direct and water-mediated hydrogen bonds mainly involving symmetry-related β-cyclodextrin molecules. The accommodation of the planar guest molecule into the β-cyclodextrin cavity determines a significant distortion of the latter from the sevenfold symmetry. Graphic
ISSN:0008-6215
1873-426X
DOI:10.1016/S0008-6215(01)00136-7