(2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-pyrrolo­[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hy­droxy­meth­yl)tetra­hydro­furan-3-ol

The title compound, C(11)H(12)FIN(4)O(3), is composed of a 7-carbapurine moiety connected via an N atom to 2-de­oxy-2-fluoro-β-d-ribose. The conformation about the N-glycosydic bond is −anti with χ = −129.0 (11)°. The glycosydic N—C bond length is 1.435 (14) Å. The sugar ring adopts an Nconformation...

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Detalles Bibliográficos
Autores principales: Li, Wei, Yang, Ruchun, Xiao, Qiang
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2014
Materias:
Organic Papers
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998288/
https://www.ncbi.nlm.nih.gov/pubmed/24764849
http://dx.doi.org/10.1107/S1600536813034995
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author Li, Wei
Yang, Ruchun
Xiao, Qiang
author_facet Li, Wei
Yang, Ruchun
Xiao, Qiang
author_sort Li, Wei
collection PubMed
description The title compound, C(11)H(12)FIN(4)O(3), is composed of a 7-carbapurine moiety connected via an N atom to 2-de­oxy-2-fluoro-β-d-ribose. The conformation about the N-glycosydic bond is −anti with χ = −129.0 (11)°. The glycosydic N—C bond length is 1.435 (14) Å. The sugar ring adopts an Nconformation with an unsymmetrical twist O-endo-C-exo ((o)T(4)). The conformation around the C—C bond is +sc, with a torsion angle of 53.0 (12)°. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, forming chains propagating along the a axis. These chains are linked via O—H⋯I and C—H⋯O hydrogen bonds, forming layers lying parallel to the c axis.
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spelling pubmed-39982882014-04-24 (2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-pyrrolo­[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hy­droxy­meth­yl)tetra­hydro­furan-3-ol Li, Wei Yang, Ruchun Xiao, Qiang Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(11)H(12)FIN(4)O(3), is composed of a 7-carbapurine moiety connected via an N atom to 2-de­oxy-2-fluoro-β-d-ribose. The conformation about the N-glycosydic bond is −anti with χ = −129.0 (11)°. The glycosydic N—C bond length is 1.435 (14) Å. The sugar ring adopts an Nconformation with an unsymmetrical twist O-endo-C-exo ((o)T(4)). The conformation around the C—C bond is +sc, with a torsion angle of 53.0 (12)°. In the crystal, mol­ecules are linked by N—H⋯O hydrogen bonds, forming chains propagating along the a axis. These chains are linked via O—H⋯I and C—H⋯O hydrogen bonds, forming layers lying parallel to the c axis. International Union of Crystallography 2014-01-08 /pmc/articles/PMC3998288/ /pubmed/24764849 http://dx.doi.org/10.1107/S1600536813034995 Text en © Li et al. 2014 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
spellingShingle Organic Papers
Li, Wei
Yang, Ruchun
Xiao, Qiang
(2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-pyrrolo­[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hy­droxy­meth­yl)tetra­hydro­furan-3-ol
title (2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-pyrrolo­[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hy­droxy­meth­yl)tetra­hydro­furan-3-ol
title_full (2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-pyrrolo­[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hy­droxy­meth­yl)tetra­hydro­furan-3-ol
title_fullStr (2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-pyrrolo­[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hy­droxy­meth­yl)tetra­hydro­furan-3-ol
title_full_unstemmed (2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-pyrrolo­[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hy­droxy­meth­yl)tetra­hydro­furan-3-ol
title_short (2R,3S,4R,5R)-5-(4-Amino-5-iodo-7H-pyrrolo­[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hy­droxy­meth­yl)tetra­hydro­furan-3-ol
title_sort (2r,3s,4r,5r)-5-(4-amino-5-iodo-7h-pyrrolo­[2,3-d]pyrimidin-7-yl)-4-fluoro-2-(hy­droxy­meth­yl)tetra­hydro­furan-3-ol
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3998288/
https://www.ncbi.nlm.nih.gov/pubmed/24764849
http://dx.doi.org/10.1107/S1600536813034995
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