1-(2,3,4,6-Tetra-O-acetyl-β-d-glucopyranosyl)-3-thioureidothiourea monohydrate

In the title compound, C16H24N4O9S2·H2O, the hexopyranosyl ring adopts a chair conformation (4 C 1), and the five substituents are in equatorial positions. In the crystal structure, extensive O—H⋯O, N—H⋯S and N—H⋯O hydrogen bonding leads to the formation of a three-dimensional network.

In the title compound, C 16 H 24 N 4 O 9 S 2 ÁH 2 O, the hexopyranosyl ring adopts a chair conformation ( 4 C 1 ), and the five substituents are in equatorial positions. In the crystal structure, extensive O-HÁ Á ÁO, N-HÁ Á ÁS and N-HÁ Á ÁO hydrogen bonding leads to the formation of a threedimensional network.
The molecular structure of compound (I) is illustrated in Fig. 1. The hexopyranosyl ring adopts a chair conformation ( 4 C 1 ), and the four substituents are in equatorial positions.
In the crystal extensive O-H···O, N-H···S and N-H···O hydrogen bonding (Table 1) leads to the formation of a three-dimensional network.

S2. Experimental
Compound (I) was prepared by refluxing together equimolar amounts of β-D-2,3,4,6-tetra-O-acetyl-glucopyranosyl isothiocyanate and thiosemicarbazide. After cooling to room temperature, water was added to the mixture and compound (I) was isolated as a white solid. Crystals, suitable for X-ray analysis, were grown from an ethyl acetate and acetonitrile (1:1 / v:v) solution by slow evaporation at room temperature.

S3. Refinement
The compound has a known chiral center [the Flack parameter is -0.16 (12) (Flack, 1983)], and for this reason the Friedel pairs were not merged. The water H-atoms were located in the difference Fourier maps and refined with distance  A view of the molecular structure of compound (I), showing the atom-labelling scheme and displacement ellipsoids drawn at the 50% probability level. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max  Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.