6-Methyl-2-pyridyl N-acetyl-1-thio-β-d-glucosaminide methanol monosolvate

In the title compound, C14H20N2O5S·CH4O, the pyranose and pyridine rings are linked through an S atom. The pyranose ring has a normal chair conformation. An intramolecular O—H⋯N hydrogen bond occurs. Intermolecular O—H⋯O, N—H⋯O, O—H⋯N and weak C—H⋯O hydrogen bonding is present in the crystal structure.

In the title compound, C 14 H 20 N 2 O 5 SÁCH 4 O, the pyranose and pyridine rings are linked through an S atom. The pyranose ring has a normal chair conformation. An intramolecular O-HÁ Á ÁN hydrogen bond occurs. Intermolecular O-HÁ Á ÁO, N-HÁ Á ÁO, O-HÁ Á ÁN and weak C-HÁ Á ÁO hydrogen bonding is present in the crystal structure.

Comment
Thioglycosides are widely employed as biological inhibitors, glycosyl donors and enzyme resistant ligands for affinity chromatography (Ashry et al., 2006). Here we report the crystal structure of the title compound (Scheme 1). The title compound crystallizes exclusively as the β anomer. The molecule contains a pyranose ring and a pyridine ring linked by a sulfur atom. The pyranose ring has a normal chair conformation, similar to that found in an α-D-glucosaminide (Harrison et al. 2007). The extensive hydrogen bonding network is present in the crystal structure, involving O-H···O, O-H···N and N-H···O hydrogen bonding (Table 1). Weak intermolecular C-H···O hydrogen bonding is also present in the crystal structure.

Refinement
H atoms were placed in calculated positions and treated using a riding-model, C-H = 0.93-0.98 Å with U iso (H) = 1.2U eq (C) or 1.5U eq (C), N-H = 0.86 with U iso (H) = 1.2U eq (N), O-H = 0.82 Å with U iso (H) = 1.5U eq (O). Fig. 1. A view of (I) showing the labeling of the non-H atoms and 50% probability ellipsoids. Dashed line indicates the hydrogen bonding.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
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 Rfactors(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )
x y z U iso */U eq