Structure of 1-(2-deoxy-<script type="math/tex">\beta</script>-d-ribopyranosyl)-5-iodouracil

De Winter, H.L.; Blaton, N.M.; Peeters, O.M.; De Ranter, C.J.; Van Aerschot, A.; Herdewijn, P.

doi:10.1107/S0108270190010526

Title

Structure of 1-(2-deoxy- $\beta$ -d-ribopyranosyl)-5-iodouracil

Author

De Winter, H.L.

Blaton, N.M.

Peeters, O.M.

De Ranter, C.J.

Van Aerschot, A.

Herdewijn, P.

Abstract

1-(2-Deoxy-beta-D-ribopyranosyl)-5-iodouracil, C9H11IN2O5, M(r) = 354.10, monoclinic, P2(1), a = 5.458 (3), b = 8.237 (4), c = 12.812 (6) angstrom, beta = 98.42 (4)-degrees, V = 569.8 (5) angstrom3, Z = 2, D(m) = 2.05, D(x) = 2.063 Mg m-3, lambda-(Mo K-alpha) = 0.71069 angstrom, mu = 2.789 mm-1, F(000) = 344, T = 293 K, final R = 0.039 for 1701 unique observed [F greater-than-or-equal-to 4-sigma(F)] reflections. The sugar ring adopts a slightly flattened chair conformation. The heterocyclic base is placed in an - ap (antiperiplanar) orientation [chi = 196.4 (3)-degrees] with respect to the sugar moiety. Of the three sugar ring substituents, only O(33') is in an axial position. The packing of the crystal is determined by three intermolecular hydrogen bonds, involving O(33'), O(2) and O(44'). 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

DOI

10.1107/S0108270190010526

Volume/pages

47 :4 (1991) , p. 835-837