Acta Crystallographica Section E

Structure Reports Online

Volume 69, Part 1 (January 2013)

metal-organic compounds

Acta Cryst. (2013). E69, m7-m8    [ doi:10.1107/S1600536812048672 ]

Potassium (1R,4R,5S,8S)-4,5,8-trihy­droxy-3-oxo-2,6-dioxabicyclo­[3.3.0]octane-4-sulfonate dihydrate

A. H. Haines and D. L. Hughes

Abstract: The title salt, K+·C6H7O9S-·2H2O, formed by reaction of dehydro-L-ascorbic acid with potassium hydrogen sulfite in water, crystallizes as colourless plates. The potassium ion is coordinated by eight O atoms arising from hy­droxy or sulfonate groups. The sulfonate group is bonded to the C atom neighbouring that of the lactone carbonyl group. As is commonly observed in crystalline L-ascorbic acid derivatives, the O atom of the primary hy­droxy group is linked to the second C atom from the lactone C atom, forming a hemi-acetal function, thereby creating a bicyclic system of two fused five-membered rings, both of which have envelope conformations with one of the shared C atoms as the flap. Addition of the sulfur nucleophile occurs from the less hindered face. One of the two independent lattice water mol­ecules has hydrogen bonds to sulfonate O atoms of two different anions and is the acceptor of bonds from hy­droxy groups of two further anions; the second lattice water mol­ecule donates to the carbonyl and a hy­droxy O atom in different anions, and accepts from a hy­droxy O atom in a further anion. Thus, through K-O coordination and hydrogen bonds, the potassium cations, sulfonate anions and water mol­ecules are linked in a three-dimensional network.

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