Open Access4‐Deoxy‐4‐fluoro‐β‐ d ‐glucopyranose
Author(s) -
Zhang Wenhui,
Oliver Allen G.,
Serianni Anthony S.
Publication year - 2010
Publication title -
acta crystallographica section c
Language(s) - English
Resource type - Journals
eISSN - 1600-5759
pISSN - 0108-2701
DOI - 10.1107/s0108270110034001
Subject(s) - conformational isomerism , crystallography , chemistry , hydroxymethyl , hydrogen bond , cyclohexane conformation , intermolecular force , crystal structure , stereochemistry , dihedral angle , ring (chemistry) , molecule , organic chemistry
4‐Deoxy‐4‐fluoro‐β‐ d ‐glucopyranose, C 6 H 11 FO 5 , (I), crystallizes from water at room temperature in a slightly distorted 4 C 1 chair conformation. The observed chair distortion differs from that observed in β‐ d ‐glucopyranose [Kouwijzer, van Eijck, Kooijman & Kroon (1995). Acta Cryst. B 51 , 209–220], (II), with the former skewed toward a B C3,O5 (boat) conformer and the latter toward an O5 TB C2 (twist–boat) conformer, based on Cremer–Pople analysis. The exocyclic hydroxymethyl group conformations in (I) and (II) are similar; in both cases, the O—C—C—O torsion angle is ∼−60° ( gg conformer). Intermolecular hydrogen bonding in the crystal structures of (I) and (II) is conserved in that identical patterns of donors and acceptors are observed for the exocyclic substituents and the ring O atom of each monosaccharide. Inspection of the crystal packing structures of (I) and (II) reveals an essentially identical packing configuration.