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(E)-3,3′,4,4′,7,7′,8,8′-Octamethyl-2H,2′H-1,1′-bi(cyclopenta[fg]acenaphthylenylidene)-2,2′,5,5′,6,6′-hexaone dichloromethane monosolvate
The title compound, C(36)H(24)O(6)·CH(2)Cl(2), is a dimer of two essentially planar (r.m.s., deviations of fitted plane of 14 pyracene C atoms = 0.0539 and 0.0543 Å) tetracyclic pyracene frameworks (each with four methyl groups and three carbonyl groups on the peripheral carbon atoms) twisted along...
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/PMC3344573/ https://www.ncbi.nlm.nih.gov/pubmed/22590335 http://dx.doi.org/10.1107/S1600536812016091 |
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author | McCandless, Gregory T. Sygula, Andrzej Rabideau, Peter W. Watkins, Steven F. Fronczek, Frank R. |
author_facet | McCandless, Gregory T. Sygula, Andrzej Rabideau, Peter W. Watkins, Steven F. Fronczek, Frank R. |
author_sort | McCandless, Gregory T. |
collection | PubMed |
description | The title compound, C(36)H(24)O(6)·CH(2)Cl(2), is a dimer of two essentially planar (r.m.s., deviations of fitted plane of 14 pyracene C atoms = 0.0539 and 0.0543 Å) tetracyclic pyracene frameworks (each with four methyl groups and three carbonyl groups on the peripheral carbon atoms) twisted along a central C=C bond with an angle of 50.78 (3)° at 90 K. There are notably long Csp (2)—Csp (2) bonds associated with the carbonyl groups, the longest being 1.601 (3) Å between two carbonyl C atoms. There are also intermolecular carbonyl⋯carbonyl interactions of both parallel and antiparallel types, with C⋯O distances in the range 3.041 (3) to 3.431 (2) Å. This compound is of interest with respect to the synthesis of fullerene fragments, such as corannulene and semibuckminsterfullerene derivatives (or ‘buckybowls’), and is a side product of the previously reported oxidation reaction. Structural details, such as planarity analysis of fused rings, out-of-plane deviation of substituents, intermolecular interactions, and longer than typical bond lengths, will be discussed as well as comparisons to structurally related compounds. |
format | Online Article Text |
id | pubmed-3344573 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2012 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-33445732012-05-15 (E)-3,3′,4,4′,7,7′,8,8′-Octamethyl-2H,2′H-1,1′-bi(cyclopenta[fg]acenaphthylenylidene)-2,2′,5,5′,6,6′-hexaone dichloromethane monosolvate McCandless, Gregory T. Sygula, Andrzej Rabideau, Peter W. Watkins, Steven F. Fronczek, Frank R. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(36)H(24)O(6)·CH(2)Cl(2), is a dimer of two essentially planar (r.m.s., deviations of fitted plane of 14 pyracene C atoms = 0.0539 and 0.0543 Å) tetracyclic pyracene frameworks (each with four methyl groups and three carbonyl groups on the peripheral carbon atoms) twisted along a central C=C bond with an angle of 50.78 (3)° at 90 K. There are notably long Csp (2)—Csp (2) bonds associated with the carbonyl groups, the longest being 1.601 (3) Å between two carbonyl C atoms. There are also intermolecular carbonyl⋯carbonyl interactions of both parallel and antiparallel types, with C⋯O distances in the range 3.041 (3) to 3.431 (2) Å. This compound is of interest with respect to the synthesis of fullerene fragments, such as corannulene and semibuckminsterfullerene derivatives (or ‘buckybowls’), and is a side product of the previously reported oxidation reaction. Structural details, such as planarity analysis of fused rings, out-of-plane deviation of substituents, intermolecular interactions, and longer than typical bond lengths, will be discussed as well as comparisons to structurally related compounds. International Union of Crystallography 2012-04-21 /pmc/articles/PMC3344573/ /pubmed/22590335 http://dx.doi.org/10.1107/S1600536812016091 Text en © McCandless et al. 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 McCandless, Gregory T. Sygula, Andrzej Rabideau, Peter W. Watkins, Steven F. Fronczek, Frank R. (E)-3,3′,4,4′,7,7′,8,8′-Octamethyl-2H,2′H-1,1′-bi(cyclopenta[fg]acenaphthylenylidene)-2,2′,5,5′,6,6′-hexaone dichloromethane monosolvate |
title | (E)-3,3′,4,4′,7,7′,8,8′-Octamethyl-2H,2′H-1,1′-bi(cyclopenta[fg]acenaphthylenylidene)-2,2′,5,5′,6,6′-hexaone dichloromethane monosolvate |
title_full | (E)-3,3′,4,4′,7,7′,8,8′-Octamethyl-2H,2′H-1,1′-bi(cyclopenta[fg]acenaphthylenylidene)-2,2′,5,5′,6,6′-hexaone dichloromethane monosolvate |
title_fullStr | (E)-3,3′,4,4′,7,7′,8,8′-Octamethyl-2H,2′H-1,1′-bi(cyclopenta[fg]acenaphthylenylidene)-2,2′,5,5′,6,6′-hexaone dichloromethane monosolvate |
title_full_unstemmed | (E)-3,3′,4,4′,7,7′,8,8′-Octamethyl-2H,2′H-1,1′-bi(cyclopenta[fg]acenaphthylenylidene)-2,2′,5,5′,6,6′-hexaone dichloromethane monosolvate |
title_short | (E)-3,3′,4,4′,7,7′,8,8′-Octamethyl-2H,2′H-1,1′-bi(cyclopenta[fg]acenaphthylenylidene)-2,2′,5,5′,6,6′-hexaone dichloromethane monosolvate |
title_sort | (e)-3,3′,4,4′,7,7′,8,8′-octamethyl-2h,2′h-1,1′-bi(cyclopenta[fg]acenaphthylenylidene)-2,2′,5,5′,6,6′-hexaone dichloromethane monosolvate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3344573/ https://www.ncbi.nlm.nih.gov/pubmed/22590335 http://dx.doi.org/10.1107/S1600536812016091 |
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