The crystal structure of 1,2,3,4,6-penta-O-benzoyl-α-d-mannopyranose: observation of CH⋯π interaction as a surrogate to OH⋯O interaction of a free sugar

The crystal structure of the title compound was determined by X-ray crystallography. The compound crystallized in the orthorhombic space group P212121 with four molecules in the unit cell with a=9.170(2), b=9.873 (2), c=38.831(8) Å. The structure was refined to a R index of 0.041 for 7907 independent reflections. The mannopyranose unit adopts a distorted 4C1 conformation. The structure depicts unique network of CH⋯π interactions, very closely resembling the pattern of OH⋯O interactions in free sugars. This intriguing and rare observation points to a notion that the supramolecular organization pertaining to a sugar is in-built in the pyranose ring itself.

Single crystal X-ray analysis of the title compound reveals the complete control of molecular packing through an exclusive CH⋯π interaction. That this interaction can surrogate naturally occurring OH⋯O interaction is also observed.Figure optionsDownload as PowerPoint slide