Acta Crystallographica, Section C: Crystal Structure Communications p. 1215 - 1218 (1996)
Update date:2022-09-26
Topics:
Robinson, Paul D.
Meyers, Cal Y.
Kolb, Vera M.
Colloton, Patricia A.
The first example of a crystalline urazole nucleoside has been synthesized from the reaction of D-deoxyribose with urazole and characterized by X-ray crystallography as a single α-pyranoside diastereomer [IUPAC name: 1-(2-deoxy-α-D-erythro-pentopyranosyl)-1(R),2(R),4-triazolidine-3,5-dione, C7H11N3O5]. The pyranosyl group and H atom on the two pyramidal hydrazidic N atoms have an R,R-trans configuration, and the H atom on the trigonal imidic N atom is coplanar with the ring. Intermolecular hydrogen bonding is extensive and involves pyranose-pyranose, pyranose-urazole and urazole-urazole interactions. Each molecule is linked via eight hydrogen bonds to six surrounding molecules in which the urazole hydrazidic N(H) atom and imidic N atom are donors and carbonyl O atoms are acceptors, and the pyranose hydroxylic O atoms are donors as well as acceptors. The pyranose ring O atom does not participate in conventional hydrogen bonding but may be involved in a weak intermolecular C - H...O interaction.
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