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Dimethyl 1-(4-methylphenyl)-8-(thiophen-2-yl)-11-oxatricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-9,10-dicarboxylate
The title compound, C(25)H(20)O(5)S, is the product of a Diels–Alder reaction. The molecule consists of a fused tricyclic system containing two five-membered rings and one six-membered ring. The five-membered rings both show an envelope conformation with the O atom at the flap, whereas the six-memb...
Autores principales: | , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3629529/ https://www.ncbi.nlm.nih.gov/pubmed/23634047 http://dx.doi.org/10.1107/S1600536813005308 |
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author | Balakrishnan, B. Nandakumar, Meganathan Seshadri, Pandamangalam R. Mohanakrishnan, Arasambattu K. |
author_facet | Balakrishnan, B. Nandakumar, Meganathan Seshadri, Pandamangalam R. Mohanakrishnan, Arasambattu K. |
author_sort | Balakrishnan, B. |
collection | PubMed |
description | The title compound, C(25)H(20)O(5)S, is the product of a Diels–Alder reaction. The molecule consists of a fused tricyclic system containing two five-membered rings and one six-membered ring. The five-membered rings both show an envelope conformation with the O atom at the flap, whereas the six-membered ring adopts a boat conformation. The thiophene ring is disordered over two sets of sites with an occupancy ratio of 0.53 (1):0.47 (1). The dihedral angles between the 4-methylphenyl ring and the major and minor components of the thiophene ring are 66.3 (1) and 67.9 (1)°, respectively, while the dihedral angle between the disordered thiophenyl components is 3.1 (1)°. The mean plane of the tricyclic ring system makes dihedral angles of 35.8 (1), 30.8 (1) and 32.8 (1)°, respectively, with the 4-methylphenyl ring and the major and minor components of the thiophenyl ring. In the crystal, inversion dimers are formed through pairs of C—H⋯π interactions. In addition, C—H⋯O interactions are observed. |
format | Online Article Text |
id | pubmed-3629529 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-36295292013-04-30 Dimethyl 1-(4-methylphenyl)-8-(thiophen-2-yl)-11-oxatricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-9,10-dicarboxylate Balakrishnan, B. Nandakumar, Meganathan Seshadri, Pandamangalam R. Mohanakrishnan, Arasambattu K. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(25)H(20)O(5)S, is the product of a Diels–Alder reaction. The molecule consists of a fused tricyclic system containing two five-membered rings and one six-membered ring. The five-membered rings both show an envelope conformation with the O atom at the flap, whereas the six-membered ring adopts a boat conformation. The thiophene ring is disordered over two sets of sites with an occupancy ratio of 0.53 (1):0.47 (1). The dihedral angles between the 4-methylphenyl ring and the major and minor components of the thiophene ring are 66.3 (1) and 67.9 (1)°, respectively, while the dihedral angle between the disordered thiophenyl components is 3.1 (1)°. The mean plane of the tricyclic ring system makes dihedral angles of 35.8 (1), 30.8 (1) and 32.8 (1)°, respectively, with the 4-methylphenyl ring and the major and minor components of the thiophenyl ring. In the crystal, inversion dimers are formed through pairs of C—H⋯π interactions. In addition, C—H⋯O interactions are observed. International Union of Crystallography 2013-03-06 /pmc/articles/PMC3629529/ /pubmed/23634047 http://dx.doi.org/10.1107/S1600536813005308 Text en © Balakrishnan et al. 2013 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 Balakrishnan, B. Nandakumar, Meganathan Seshadri, Pandamangalam R. Mohanakrishnan, Arasambattu K. Dimethyl 1-(4-methylphenyl)-8-(thiophen-2-yl)-11-oxatricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-9,10-dicarboxylate |
title | Dimethyl 1-(4-methylphenyl)-8-(thiophen-2-yl)-11-oxatricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-9,10-dicarboxylate |
title_full | Dimethyl 1-(4-methylphenyl)-8-(thiophen-2-yl)-11-oxatricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-9,10-dicarboxylate |
title_fullStr | Dimethyl 1-(4-methylphenyl)-8-(thiophen-2-yl)-11-oxatricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-9,10-dicarboxylate |
title_full_unstemmed | Dimethyl 1-(4-methylphenyl)-8-(thiophen-2-yl)-11-oxatricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-9,10-dicarboxylate |
title_short | Dimethyl 1-(4-methylphenyl)-8-(thiophen-2-yl)-11-oxatricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-9,10-dicarboxylate |
title_sort | dimethyl 1-(4-methylphenyl)-8-(thiophen-2-yl)-11-oxatricyclo[6.2.1.0(2,7)]undeca-2,4,6,9-tetraene-9,10-dicarboxylate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3629529/ https://www.ncbi.nlm.nih.gov/pubmed/23634047 http://dx.doi.org/10.1107/S1600536813005308 |
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