Crystal structure of sodium (1S)-d-mannit-1-ylsulfonate

Abstract

The title salt, Na+·C6H13O9S− [systematic name: sodium (1S,2S,3S,4R,5R)-1,2,3,4,5,6-hexahydroxyhexane-1-sulfonate], is formed by reaction of d-mannose with sodium bisulfite (sodium hydrogen sulfite) in water. The anion has an open-chain structure with the S atom and the C atoms of the carbohydrate chain forming an essentially planar zigzag chain in which the absolute values of the torsion angles lie between 173.6 (2) and 179.9 (3)°. The sodium cations are penta-coordinated by O atoms, with one link to a carbohydrate O atom and four to O atoms of sulfonate residues in separate anions, thus creating a three-dimensional network. The carbohydrate anions are arranged in a head (–SO3−) to head (–SO3−) arrangement, thereby forming two parallel sheets linked through coordination to sodium ions, with each sheet containing intermolecular hydrogen bonds between the anionic residues. Unusually, the double sheets are not connected to neighbouring sets of double sheets, either by ion coordination or intermolecular hydrogen bonding.

Keywords

• crystal structure
• D-mannose bisulfite adduct
• sodium hydrogen sulfite
• sodium metabisulfite