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Redetermined structure, inter­molecular inter­actions and absolute configuration of royleanone

The structure of the title diterpenoid, C(20)H(28)O(3), {systematic name: (4bS,8aS)-3-hy­droxy-2-isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenanthrene-1,4-dione} is confirmed [Eugster et al. (1993 ▶). Private communication (refcode HACGUN). CCDC, Union Road, Cambridge] and its packin...

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Autores principales: Fun, Hoong-Kun, Chantrapromma, Suchada, Salae, Abdul Wahab, Razak, Ibrahim Abdul, Karalai, Chatchanok
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089143/
https://www.ncbi.nlm.nih.gov/pubmed/21754362
http://dx.doi.org/10.1107/S1600536811011457
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author Fun, Hoong-Kun
Chantrapromma, Suchada
Salae, Abdul Wahab
Razak, Ibrahim Abdul
Karalai, Chatchanok
author_facet Fun, Hoong-Kun
Chantrapromma, Suchada
Salae, Abdul Wahab
Razak, Ibrahim Abdul
Karalai, Chatchanok
author_sort Fun, Hoong-Kun
collection PubMed
description The structure of the title diterpenoid, C(20)H(28)O(3), {systematic name: (4bS,8aS)-3-hy­droxy-2-isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenanthrene-1,4-dione} is confirmed [Eugster et al. (1993 ▶). Private communication (refcode HACGUN). CCDC, Union Road, Cambridge] and its packing is now described. Its absolute structure was established by refinement against data collected with Cu radiation: the two stereogenic centres both have S configurations. One cyclo­hexane ring adopts a chair conformation whereas the other cyclo­hexane ring is in a half-chair conformation and the benzoquinone ring is slightly twisted. An intra­molecular O—H⋯O hydrogen bond generates an S(5) ring motif. In the crystal, mol­ecules are linked into chains along [010] by O—H⋯O hydrogen bonds and weak C—H⋯O inter­actions. The packing also features C⋯O [3.131 (3) Å] short contacts.
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spelling pubmed-30891432011-07-13 Redetermined structure, inter­molecular inter­actions and absolute configuration of royleanone Fun, Hoong-Kun Chantrapromma, Suchada Salae, Abdul Wahab Razak, Ibrahim Abdul Karalai, Chatchanok Acta Crystallogr Sect E Struct Rep Online Organic Papers The structure of the title diterpenoid, C(20)H(28)O(3), {systematic name: (4bS,8aS)-3-hy­droxy-2-isopropyl-4b,8,8-trimethyl-4b,5,6,7,8,8a,9,10-octa­hydro­phenanthrene-1,4-dione} is confirmed [Eugster et al. (1993 ▶). Private communication (refcode HACGUN). CCDC, Union Road, Cambridge] and its packing is now described. Its absolute structure was established by refinement against data collected with Cu radiation: the two stereogenic centres both have S configurations. One cyclo­hexane ring adopts a chair conformation whereas the other cyclo­hexane ring is in a half-chair conformation and the benzoquinone ring is slightly twisted. An intra­molecular O—H⋯O hydrogen bond generates an S(5) ring motif. In the crystal, mol­ecules are linked into chains along [010] by O—H⋯O hydrogen bonds and weak C—H⋯O inter­actions. The packing also features C⋯O [3.131 (3) Å] short contacts. International Union of Crystallography 2011-04-07 /pmc/articles/PMC3089143/ /pubmed/21754362 http://dx.doi.org/10.1107/S1600536811011457 Text en © Fun et al. 2011 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
Fun, Hoong-Kun
Chantrapromma, Suchada
Salae, Abdul Wahab
Razak, Ibrahim Abdul
Karalai, Chatchanok
Redetermined structure, inter­molecular inter­actions and absolute configuration of royleanone
title Redetermined structure, inter­molecular inter­actions and absolute configuration of royleanone
title_full Redetermined structure, inter­molecular inter­actions and absolute configuration of royleanone
title_fullStr Redetermined structure, inter­molecular inter­actions and absolute configuration of royleanone
title_full_unstemmed Redetermined structure, inter­molecular inter­actions and absolute configuration of royleanone
title_short Redetermined structure, inter­molecular inter­actions and absolute configuration of royleanone
title_sort redetermined structure, inter­molecular inter­actions and absolute configuration of royleanone
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3089143/
https://www.ncbi.nlm.nih.gov/pubmed/21754362
http://dx.doi.org/10.1107/S1600536811011457
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