Acta Crystallographica Section C

Crystal Structure Communications

Volume 64, Part 8 (August 2008)

organic compounds

 

7-Deaza-2'-deoxyinosine: a nucleoside showing ambiguous base-pairing properties against the four canonical DNA constituents

F. Seela, X. Ming, H. Eickmeier and H. Reuter

Abstract: The title compound [systematic name: 7-(2-deoxy--D-erythro-pentofuranosyl)-3,7-dihydro-4H-pyrrolo[2,3-d]pyrimidin-4-one], C₁₁H₁₃N₃O₄, represents an acid-stable derivative of 2'-deoxyinosine. It exhibits an anti glycosylic bond conformation, with a torsion angle of 113.30 (15)°. The furanose moiety adopts an S-type sugar pucker ⁴T₃, with P = 221.8 (1)° and _m = 40.4 (1)°. The conformation at the exocyclic C4'-C5' bond of the furanose ring is ap (trans), with = 167.14 (10)°. The extended structure forms a three-dimensional hydrogen-bond network involving O-HO, N-HO and C-HO hydrogen bonds. The title compound forms an uncommon hydrogen bond between a CH group of the pyrrole system and the ring O atom of the sugar moiety of a neighbouring molecule.

Formula: C₁₁H₁₃N₃O₄

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