Title
Structures of 1-(2,3-dideoxy-erythro-<tex>$\alpha$</tex>-d-hexopyranosyl)thymine and the 1-(2,3-dideoxy-erythro-<tex>$\beta$</tex>-d-hexopyranosyl)thymine.dioxane complex
Author
Faculty/Department
Faculty of Pharmaceutical, Biomedical and Veterinary Sciences. Pharmacy
Publication type
article
Publication
Copenhagen ,
Subject
Chemistry
Source (journal)
Acta crystallographica: section C: crystal structure communications. - Copenhagen
Volume/pages
47(1991) :4 , p. 838-842
ISSN
0108-2701
ISI
A1991FJ77300050
Carrier
E
Target language
English (eng)
Full text (Publishers DOI)
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.
E-info
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