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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...

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Autores principales: Balakrishnan, B., Nandakumar, Meganathan, Seshadri, Pandamangalam R., Mohanakrishnan, Arasambattu K.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
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.
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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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