2′-Deoxy-2′,2′-difluorocytidine monohydrochloride (Gemcitabine hydrochloride)

Abstract

Gemcitabine hydro­chloride (2′-deoxy-2′,2′-di­fluoro­cytidine hydro­chloride), C9H12N3F2O4+·Cl−, is a β-nucleoside that is of pharmaceutical interest as an antitumor agent. The N atom of the cytidine ring is protonated due to salt formation. The sugar residue adopts a C3′-endo and C4′-exo conformation. In the asymmetric unit, gemcitabine cations and chloride ions are linked by N—H⋯Cl hydrogen bonds. In the crystal structure, screw-related gemcitabine cations are linked by O—H⋯O hydrogen bonds to form molecular columns along the c axis and adjacent columns are interlinked by N—H⋯Cl and O—H⋯Cl hydrogen bonds.