4-Amino-7-(2-deoxy-2-fluoro-β-D-arabinofuranosyl)-5-fluoro-7H-pyrrolo[2,3-d]pyrimidine: a bis-fluorinated analogue of 2′-deoxytubercidin

Abstract

The title compound, C 11 H 12 F 2 N 4 O 3 , exhibits an anti glycosylic bond conformation, with a torsion angle Χ = -117.8 (2)°. The sugar pucker is N-type (C4'-exo, between 3 T 4 and E 4 , with P = 45.3° and τ m = 41.3°). The conformation around the exocyclic C-C bond is -ap (trans), with a torsion angle y = -177.46 (15)°. The nucleobases are stacked head-to-head. The crystal structure is characterized by a three-dimensional hydrogen-bond network involving N-H···O, O-H···O and O-H···N hydrogen bonds.