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  • Title: 1,7-Dideaza-2'-deoxy-6-nitronebularine: a pyrrolo[2,3-b]pyridine nucleoside with an intramolecular hydrogen bond stabilizing the syn conformation.
    Author: Yang H, Budow S, Eickmeier H, Reuter H, Seela F.
    Journal: Acta Crystallogr C; 2013 Aug; 69(Pt 8):892-5. PubMed ID: 23907884.
    Abstract:
    The title compound [systematic name: 1-(2-deoxy-β-D-erythro-pentofuranosyl)-4-nitro-1H-pyrrolo[2,3-b]pyridine], C₁₂H₁₃N₃O₅, forms an intramolecular hydrogen bond between the pyridine N atom as acceptor and the 5'-hydroxy group of the sugar residue as donor. Consequently, the N-glycosylic bond exhibits a syn conformation, with a χ torsion angle of 61.6 (2)°, and the pentofuranosyl residue adopts a C2'-endo envelope conformation (²E, S-type), with P = 162.1 (1)° and τm = 36.2 (1)°. The orientation of the exocyclic C4'-C5' bond is +sc (gauche, gauche), with a torsion angle γ = 49.1 (2)°. The title nucleoside forms an ordered and stacked three-dimensional network. The pyrrole ring of one layer faces the pyridine ring of an adjacent layer. Additionally, intermolecular O-H∙∙∙O and C-H∙∙∙O hydrogen bonds stabilize the crystal structure.
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