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Subramanyam Srinivasan, Kuttikode Priya, Duraikkannu Loganathan
Published in Blackwell Munksgaard
Volume: 54
Issue: 11
Pages: 1670 - 1672
In the title compound, 1-benzamido-β-D-glucopyranose, C13H17NO6, the pyranose ring adopts the 4C1(D) conformation and the N-acetyl group exists in the Z-anti conformation. The primary alcohol group is disordered between the two permitted orientations, gg and gt. alcohol group involving O6A adopts the gg conformation, whereas the one involving O6B takes up the gt conformation, as evident from the values of the torsion angles (O5/C4)-C5-C6-(O6A/O6B) (see Table 1). Such twofold disorder occurring between two permitted orientations has been observed previously in the crystal structures of α-L-sorbopyranose and meso-erythritol (Jeffrey, 1990). The primary hydroxyl group takes up only the gg conformation in solution, as evident from the 1H NMR coupling constants, 76,5 = 2.0 and J6′,15 = 5.1Hz. The O atom at C2 is also disordered, with O2A and O2B having occupancies of 0.62 (2) and 0.38 (2), respectively. The bond geometries involving both O6 and O2 show deviations from their ideal values, which are attributed to their large disorder and displacement parameters.
About the journal
JournalActa Crystallographica Section C: Crystal Structure Communications
PublisherBlackwell Munksgaard
Open AccessNo