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Crystal structure of a nucleoside analogue, 2′,3′-dideoxy-3′-fluoro-5-chlorocytidine

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Abstract

The title compound, 1-(2,3-dideoxy-3-fluoro-β-d-erythro pentofuranos-1-yl)-5-chlorocytosine, crystallises in the orthorhombic space groupP212121 witha=5.142(1),b=14.177(2),c=15.721(2) Å,Z=4. The crystal structure was solved by the heavy atom method and refined by full-matrix least-squares method to a finalR value of 0.031 for 1629 unique observed reflections. The N-glycosidic torsion angle is −156.1(2)° and the sugar moiety is anti to the cytosine base. The sugar pucker is 32 T withP=178.2(1)° andψ=31(1)°. The atom 05′ is in a +sc conformation with respect to the furanose ring. The molecular packing in the crystal is stabilized by N-H⋯N, N-H⋯O, O-H⋯O hydrogen bonds and C-H⋯O close contacts.

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Authors and Affiliations

  1. Crystallography and Molecular Biology Division, Saha Institute of Nuclear Physics, Section 1, Block-AF, Bidhannagar, 700064, Calcutta, India

    A. K. Das & S. K. Mazumdar

  2. Centro di Strutturistica diffractometrica e departimento di chimica, university di Ferrara, I-44100, Ferrara, Italy

    V. Bertolasi

  3. Laboratorium voor Farmaceutesche Chemie, Rega Institute of Medical Research, Katholieke Universiteit, Leuven, B-3000, Leuven, Belgium

    A. Van Aerschot

Authors
  1. A. K. Das
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  2. S. K. Mazumdar
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  3. V. Bertolasi
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  4. A. Van Aerschot
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Das, A.K., Mazumdar, S.K., Bertolasi, V. et al. Crystal structure of a nucleoside analogue, 2′,3′-dideoxy-3′-fluoro-5-chlorocytidine. Journal of Crystallographic and Spectroscopic Research 23, 455–458 (1993). https://doi.org/10.1007/BF01182517

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  • DOI: https://doi.org/10.1007/BF01182517

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