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Rubrene endoperoxide acetone monosolvate

The title acetone solvate, C(42)H(28)O(2)·C(3)H(6)O [systematic name: 1,3,10,12-tetra­phenyl-19,20-dioxapenta­cyclo­[10.6.2.0(2,11).0(4,9).0(13,18)]icosa-2(11),3,5,7,9,13,15,17-octa­ene acetone monosolvate], is a photooxygenation product of rubrene (systematic name: 5,6,11,12-tetra­phenyl­tetra­cene...

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Autores principales: Shinashi, Kiyoaki, Uchida, Akira
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2012
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3343964/
https://www.ncbi.nlm.nih.gov/pubmed/22590045
http://dx.doi.org/10.1107/S1600536812008835
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author Shinashi, Kiyoaki
Uchida, Akira
author_facet Shinashi, Kiyoaki
Uchida, Akira
author_sort Shinashi, Kiyoaki
collection PubMed
description The title acetone solvate, C(42)H(28)O(2)·C(3)H(6)O [systematic name: 1,3,10,12-tetra­phenyl-19,20-dioxapenta­cyclo­[10.6.2.0(2,11).0(4,9).0(13,18)]icosa-2(11),3,5,7,9,13,15,17-octa­ene acetone monosolvate], is a photooxygenation product of rubrene (systematic name: 5,6,11,12-tetra­phenyl­tetra­cene). The mol­ecule bends at the bridgehead atoms, which are linked by the O—O transannular bond, with a dihedral angle of 49.21 (6)° between the benzene ring and the naphthalene ring system of the tetra­cene unit. In the crystal, the rubrene mol­ecules are linked by C—H⋯O hydrogen bonds into a column along the c axis. The acetone solvent mol­ecules form a dimer around a crystallographic inversion centre through a carbon­yl–carbonyl dipolar inter­action. A C—H⋯O hydrogen bond between the rubrene and acetone mol­ecules is also observed.
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spelling pubmed-33439642012-05-15 Rubrene endoperoxide acetone monosolvate Shinashi, Kiyoaki Uchida, Akira Acta Crystallogr Sect E Struct Rep Online Organic Papers The title acetone solvate, C(42)H(28)O(2)·C(3)H(6)O [systematic name: 1,3,10,12-tetra­phenyl-19,20-dioxapenta­cyclo­[10.6.2.0(2,11).0(4,9).0(13,18)]icosa-2(11),3,5,7,9,13,15,17-octa­ene acetone monosolvate], is a photooxygenation product of rubrene (systematic name: 5,6,11,12-tetra­phenyl­tetra­cene). The mol­ecule bends at the bridgehead atoms, which are linked by the O—O transannular bond, with a dihedral angle of 49.21 (6)° between the benzene ring and the naphthalene ring system of the tetra­cene unit. In the crystal, the rubrene mol­ecules are linked by C—H⋯O hydrogen bonds into a column along the c axis. The acetone solvent mol­ecules form a dimer around a crystallographic inversion centre through a carbon­yl–carbonyl dipolar inter­action. A C—H⋯O hydrogen bond between the rubrene and acetone mol­ecules is also observed. International Union of Crystallography 2012-03-10 /pmc/articles/PMC3343964/ /pubmed/22590045 http://dx.doi.org/10.1107/S1600536812008835 Text en © Shinashi and Uchida 2012 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
Shinashi, Kiyoaki
Uchida, Akira
Rubrene endoperoxide acetone monosolvate
title Rubrene endoperoxide acetone monosolvate
title_full Rubrene endoperoxide acetone monosolvate
title_fullStr Rubrene endoperoxide acetone monosolvate
title_full_unstemmed Rubrene endoperoxide acetone monosolvate
title_short Rubrene endoperoxide acetone monosolvate
title_sort rubrene endoperoxide acetone monosolvate
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3343964/
https://www.ncbi.nlm.nih.gov/pubmed/22590045
http://dx.doi.org/10.1107/S1600536812008835
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