Synthesis and crystal structure of (±)-Goniotamirenone C

The structure of the racemic version of the natural product Goniotamirenone C [racemic anti-6-(2-chloro-1-hy­droxy-2-phenyl­eth­yl)-2H-pyran-2-one, C(13)H(11)ClO(3)] at 150 K is reported. The compound crystallizes with monoclinic (P2(1)/n) symmetry and with Z′ = 2. One independent mol­ecule is order...

Descripción completa

Detalles Bibliográficos
Autores principales: Meesakul, Pornphimol, Richardson, Christopher, Laphookhieo, Surat, Pyne, Stephen G.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2020
Materias:
Research Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7643229/
https://www.ncbi.nlm.nih.gov/pubmed/33209342
http://dx.doi.org/10.1107/S2056989020013298
_version_ 1783606238793170944
author Meesakul, Pornphimol
Richardson, Christopher
Laphookhieo, Surat
Pyne, Stephen G.
author_facet Meesakul, Pornphimol
Richardson, Christopher
Laphookhieo, Surat
Pyne, Stephen G.
author_sort Meesakul, Pornphimol
collection PubMed
description The structure of the racemic version of the natural product Goniotamirenone C [racemic anti-6-(2-chloro-1-hy­droxy-2-phenyl­eth­yl)-2H-pyran-2-one, C(13)H(11)ClO(3)] at 150 K is reported. The compound crystallizes with monoclinic (P2(1)/n) symmetry and with Z′ = 2. One independent mol­ecule is ordered while the other independent mol­ecule exhibits an inter­esting whole-mol­ecule enanti­omeric disorder with occupancies of 0.846 (4) and 0.154 (4). The independent mol­ecules are hydrogen bonded with –OH⋯O=C linkages into chains that run parallel to the a axis. This structural analysis corrects our previous assignment as the syn isomer [Meesakul et al. (2020 ▸). Phytochemistry, 171, 112248–112255].
format Online
Article
Text
id pubmed-7643229
institution National Center for Biotechnology Information
language English
publishDate 2020
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-76432292020-11-17 Synthesis and crystal structure of (±)-Goniotamirenone C Meesakul, Pornphimol Richardson, Christopher Laphookhieo, Surat Pyne, Stephen G. Acta Crystallogr E Crystallogr Commun Research Communications The structure of the racemic version of the natural product Goniotamirenone C [racemic anti-6-(2-chloro-1-hy­droxy-2-phenyl­eth­yl)-2H-pyran-2-one, C(13)H(11)ClO(3)] at 150 K is reported. The compound crystallizes with monoclinic (P2(1)/n) symmetry and with Z′ = 2. One independent mol­ecule is ordered while the other independent mol­ecule exhibits an inter­esting whole-mol­ecule enanti­omeric disorder with occupancies of 0.846 (4) and 0.154 (4). The independent mol­ecules are hydrogen bonded with –OH⋯O=C linkages into chains that run parallel to the a axis. This structural analysis corrects our previous assignment as the syn isomer [Meesakul et al. (2020 ▸). Phytochemistry, 171, 112248–112255]. International Union of Crystallography 2020-10-09 /pmc/articles/PMC7643229/ /pubmed/33209342 http://dx.doi.org/10.1107/S2056989020013298 Text en © Meesakul et al. 2020 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
Meesakul, Pornphimol
Richardson, Christopher
Laphookhieo, Surat
Pyne, Stephen G.
Synthesis and crystal structure of (±)-Goniotamirenone C
title Synthesis and crystal structure of (±)-Goniotamirenone C
title_full Synthesis and crystal structure of (±)-Goniotamirenone C
title_fullStr Synthesis and crystal structure of (±)-Goniotamirenone C
title_full_unstemmed Synthesis and crystal structure of (±)-Goniotamirenone C
title_short Synthesis and crystal structure of (±)-Goniotamirenone C
title_sort synthesis and crystal structure of (±)-goniotamirenone c
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7643229/
https://www.ncbi.nlm.nih.gov/pubmed/33209342
http://dx.doi.org/10.1107/S2056989020013298
work_keys_str_mv AT meesakulpornphimol synthesisandcrystalstructureofgoniotamirenonec
AT richardsonchristopher synthesisandcrystalstructureofgoniotamirenonec
AT laphookhieosurat synthesisandcrystalstructureofgoniotamirenonec
AT pynestepheng synthesisandcrystalstructureofgoniotamirenonec

Ejemplares similares