Crystal structure and computational study of 3,4-dihy­droxy-3-hy­droxy­methyl-9-methyl-6-methyl­idene-3a,4,5,6,6a,9,9a,9b-octa­hydro­azuleno[4,5-b]furan-2,8(3H,7H)-dione

In the mol­ecule of title compound, C(15)H(20)O(6), also known as cynarinin A, the cyclo­pentane ring having twist conformation and a γ-lactone ring assuming an envelope conformation are trans- and cis-fused, respectively, to a cyclo­heptane ring adopting a twist-chair conformation. In the crystal,...

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Autores principales: Çelik, Ísmail, Akkurt, Mehmet, Akşit, Hüseyin, Erenler, Ramazan, García-Granda, Santiago
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Research Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4719805/
https://www.ncbi.nlm.nih.gov/pubmed/26870396
http://dx.doi.org/10.1107/S2056989015019623
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author Çelik, Ísmail
Akkurt, Mehmet
Akşit, Hüseyin
Erenler, Ramazan
García-Granda, Santiago
author_facet Çelik, Ísmail
Akkurt, Mehmet
Akşit, Hüseyin
Erenler, Ramazan
García-Granda, Santiago
author_sort Çelik, Ísmail
collection PubMed
description In the mol­ecule of title compound, C(15)H(20)O(6), also known as cynarinin A, the cyclo­pentane ring having twist conformation and a γ-lactone ring assuming an envelope conformation are trans- and cis-fused, respectively, to a cyclo­heptane ring adopting a twist-chair conformation. In the crystal, O—H⋯O hydrogen bonds link neighbouring mol­ecules, forming a three-dimensional network. Theoretical calculations of the mol­ecular structure using the CNDO approximation and MOPAC PM3 geometry optimization are in satisfactory agreement with the results of the X-ray structure analysis.
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spelling pubmed-47198052016-02-11 Crystal structure and computational study of 3,4-dihy­droxy-3-hy­droxy­methyl-9-methyl-6-methyl­idene-3a,4,5,6,6a,9,9a,9b-octa­hydro­azuleno[4,5-b]furan-2,8(3H,7H)-dione Çelik, Ísmail Akkurt, Mehmet Akşit, Hüseyin Erenler, Ramazan García-Granda, Santiago Acta Crystallogr E Crystallogr Commun Research Communications In the mol­ecule of title compound, C(15)H(20)O(6), also known as cynarinin A, the cyclo­pentane ring having twist conformation and a γ-lactone ring assuming an envelope conformation are trans- and cis-fused, respectively, to a cyclo­heptane ring adopting a twist-chair conformation. In the crystal, O—H⋯O hydrogen bonds link neighbouring mol­ecules, forming a three-dimensional network. Theoretical calculations of the mol­ecular structure using the CNDO approximation and MOPAC PM3 geometry optimization are in satisfactory agreement with the results of the X-ray structure analysis. International Union of Crystallography 2015-11-04 /pmc/articles/PMC4719805/ /pubmed/26870396 http://dx.doi.org/10.1107/S2056989015019623 Text en © Çelik et al. 2015 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 Research Communications
Çelik, Ísmail
Akkurt, Mehmet
Akşit, Hüseyin
Erenler, Ramazan
García-Granda, Santiago
Crystal structure and computational study of 3,4-dihy­droxy-3-hy­droxy­methyl-9-methyl-6-methyl­idene-3a,4,5,6,6a,9,9a,9b-octa­hydro­azuleno[4,5-b]furan-2,8(3H,7H)-dione
title Crystal structure and computational study of 3,4-dihy­droxy-3-hy­droxy­methyl-9-methyl-6-methyl­idene-3a,4,5,6,6a,9,9a,9b-octa­hydro­azuleno[4,5-b]furan-2,8(3H,7H)-dione
title_full Crystal structure and computational study of 3,4-dihy­droxy-3-hy­droxy­methyl-9-methyl-6-methyl­idene-3a,4,5,6,6a,9,9a,9b-octa­hydro­azuleno[4,5-b]furan-2,8(3H,7H)-dione
title_fullStr Crystal structure and computational study of 3,4-dihy­droxy-3-hy­droxy­methyl-9-methyl-6-methyl­idene-3a,4,5,6,6a,9,9a,9b-octa­hydro­azuleno[4,5-b]furan-2,8(3H,7H)-dione
title_full_unstemmed Crystal structure and computational study of 3,4-dihy­droxy-3-hy­droxy­methyl-9-methyl-6-methyl­idene-3a,4,5,6,6a,9,9a,9b-octa­hydro­azuleno[4,5-b]furan-2,8(3H,7H)-dione
title_short Crystal structure and computational study of 3,4-dihy­droxy-3-hy­droxy­methyl-9-methyl-6-methyl­idene-3a,4,5,6,6a,9,9a,9b-octa­hydro­azuleno[4,5-b]furan-2,8(3H,7H)-dione
title_sort crystal structure and computational study of 3,4-dihy­droxy-3-hy­droxy­methyl-9-methyl-6-methyl­idene-3a,4,5,6,6a,9,9a,9b-octa­hydro­azuleno[4,5-b]furan-2,8(3h,7h)-dione
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4719805/
https://www.ncbi.nlm.nih.gov/pubmed/26870396
http://dx.doi.org/10.1107/S2056989015019623
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