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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...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2012
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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. |
format | Online Article Text |
id | pubmed-3343964 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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 |
work_keys_str_mv | AT shinashikiyoaki rubreneendoperoxideacetonemonosolvate AT uchidaakira rubreneendoperoxideacetonemonosolvate |