title: 2'-Deoxy-5-propynylcytidine: a nucleoside forming two solid-state conformations.
abstract: The title compound, 4-amino-1-(2-deoxy-beta-D-erythropentofuranosyl)-5-(prop-1-ynyl)pyrimidin-2(1H)-one, C12H15N3O4, shows two conformations in the crystalline state which differ mainly in the glycosylic bond torsion angle and the sugar pucker. Both molecules exhibit an anti glycosylic bond conformation, with torsion angles chi = -135.0 (2) and -156.4 (2) degrees for molecules 1 and 2, respectively. The sugar moieties show a twisted C2'-endo sugar pucker (S-type), with P = 173.3 and 192.5 degrees for molecules 1 and 2, respectively. The crystal structure is characterized by a three-dimensional network that is stabilized by several intermolecular hydrogen bonds between the two conformers.
authors.affiliation: Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastrasse 7, 49069 Osnabrück, Germany. frank.seela@uni-osnabrueck.de
authors.forename: Frank
authors.initials: F
authors.lastname: Seela
authors.forename: Simone
authors.initials: S
authors.lastname: Budow
authors.forename: Henning
authors.initials: H
authors.lastname: Eickmeier
authors.forename: Hans
authors.initials: H
authors.lastname: Reuter
mesh_terms: D018360:Crystallography, X-Ray; D003841:Deoxycytidine / Q000031:analogs & derivatives* / Q000737:chemistry; D006860:Hydrogen Bonding; D008958:Models, Molecular; D008968:Molecular Conformation; D009705:Nucleosides / Q000737:chemistry*
chemical_list: C518429:2'-deoxy-5-propynylcytidine; D009705:Nucleosides; D003841:Deoxycytidine