Publication
Title
Structures of 1-(2,3-dideoxy-erythro--d-hexopyranosyl)thymine and the 1-(2,3-dideoxy-erythro--d-hexopyranosyl)thymine.dioxane complex
Author
Abstract
(1) 1-(2,3-Dideoxy-erythro-alpha-D-hexopyranosyl)thymine, C11H16N2O5, M(r) = 256.26, orthorhombic, P2(1)2(1)2(1), a = 4.871 (2), b = 13.182 (7), c = 18.678 (9) angstrom, V = 1199 (1) angstrom3, Z = 4, D(m) = 1.43, D(x) = 1.419 Mg m-3, lambda-(Mo K-alpha) = 0.71069 angstrom, mu = 0.106 mm-1, F(000) = 544, room temperature, final R = 0.032 for 1197 unique observed [F greater-than-or-equal-to 4-sigma(F)] reflections. (II) 1-(2,3-Dideoxy-erythro-beta-D-hexopyranosyl)thymine.dioxane complex, C11H16N2O5.-C4H8O2, M(r) = 344.36, monoclinic, C2, a = 17.23 (1), b = 7.651 (4), c = 13.401 (8) angstrom, beta = 101.14 (5)-degrees, V = 1734 (2) angstrom3, Z = 4, D(m) = 1.32, D(x) = 1.320 Mg m-3, lambda-(Mo K-alpha) = 0.71069 angstrom, mu = 0.098 mm-1, F(000) = 736, room temperature, final R = 0.048 for 1704 unique observed [F greater-than-or-equal-to 4-sigma(F)] reflections. In both structures the pyranose ring adopts a chair conformation flattened at the C(4') and C(1') apex for (I) and (II) respectively. For compound (I), with an intramolecular hydrogen bond between O(55')-H(1) and O(2), the H(1)-O(55')-C(55')-C(5') torsion angle is - sc (synclinal), while in compound (II), where no intramolecular hydrogen bonds are present, this torsion angle is in a + sc orientation. The N-glycosidic torsion angle chi is + sc and - ac (anticlinal) for (I) and (II) respectively. The dioxane molecule in (II) is suspected to be disordered. The packing of both crystals is determined by intermolecular hydrogen bonds. The conformational parameters are in accordance with the IUPAC-IUB Joint Commission on Biochemical Nomenclature [Pure Appl. Chem. (1983), 55, 1273-1280] guidelines.
Language
English
Source (journal)
Acta crystallographica: section C: crystal structure communications. - Copenhagen
Publication
Copenhagen : 1991
ISSN
0108-2701
Volume/pages
47:4(1991), p. 838-842
ISI
A1991FJ77300050
Full text (Publishers DOI)
Full text (publishers version - intranet only)
UAntwerpen
Faculty/Department
Publication type
Subject
External links
Web of Science
Record
Identification
Creation 11.12.2013
Last edited 20.04.2017