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(±)-trans-6,7-Dimethoxy-1-oxo-3-(2-thienyl)isochroman-4-carboxylic acid
The title compound, C(16)H(14)O(6)S, was synthesized by the reaction of 6,7-dimethoxyhomophthalic anhydride with thiophene-2-carbaldehyde in the presence of 4-(dimethylamino)pyridine (DMAP) as a basic catalyst. The thiophene ring of the title molecule is disordered over two sites with occupanci...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969835/ https://www.ncbi.nlm.nih.gov/pubmed/21583225 http://dx.doi.org/10.1107/S1600536809018844 |
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author | Akkurt, Mehmet Baktır, Zeliha Bogdanov, Milen G. Svinyarov, Ivan V. Büyükgüngör, Orhan |
author_facet | Akkurt, Mehmet Baktır, Zeliha Bogdanov, Milen G. Svinyarov, Ivan V. Büyükgüngör, Orhan |
author_sort | Akkurt, Mehmet |
collection | PubMed |
description | The title compound, C(16)H(14)O(6)S, was synthesized by the reaction of 6,7-dimethoxyhomophthalic anhydride with thiophene-2-carbaldehyde in the presence of 4-(dimethylamino)pyridine (DMAP) as a basic catalyst. The thiophene ring of the title molecule is disordered over two sites with occupancies of 0.877 (3) and 0.123 (3). The disorder corresponds to an approximate 180° rotation of the thiophene ring with respect to the C—C bond linking it to the rest of the molecule. The six-membered ring of the 3,4-dihydroisochromanone ring system is not planar [puckering parameters Q (T) = 0.571 (2) Å, θ = 115.2 (2)° and ϕ = 99.1 (2)°]. The benzene ring of the 3,4-dihydroisochromanone ring system makes dihedral angles of 75.0 (2) and 77.2 (5)° with the disordered thiophene rings. Intermolecular O—H⋯O and C—H⋯O hydrogen bonds, as well as C—H⋯π interactions, lead to the observed supramolecular structure. |
format | Text |
id | pubmed-2969835 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29698352010-12-30 (±)-trans-6,7-Dimethoxy-1-oxo-3-(2-thienyl)isochroman-4-carboxylic acid Akkurt, Mehmet Baktır, Zeliha Bogdanov, Milen G. Svinyarov, Ivan V. Büyükgüngör, Orhan Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(16)H(14)O(6)S, was synthesized by the reaction of 6,7-dimethoxyhomophthalic anhydride with thiophene-2-carbaldehyde in the presence of 4-(dimethylamino)pyridine (DMAP) as a basic catalyst. The thiophene ring of the title molecule is disordered over two sites with occupancies of 0.877 (3) and 0.123 (3). The disorder corresponds to an approximate 180° rotation of the thiophene ring with respect to the C—C bond linking it to the rest of the molecule. The six-membered ring of the 3,4-dihydroisochromanone ring system is not planar [puckering parameters Q (T) = 0.571 (2) Å, θ = 115.2 (2)° and ϕ = 99.1 (2)°]. The benzene ring of the 3,4-dihydroisochromanone ring system makes dihedral angles of 75.0 (2) and 77.2 (5)° with the disordered thiophene rings. Intermolecular O—H⋯O and C—H⋯O hydrogen bonds, as well as C—H⋯π interactions, lead to the observed supramolecular structure. International Union of Crystallography 2009-05-23 /pmc/articles/PMC2969835/ /pubmed/21583225 http://dx.doi.org/10.1107/S1600536809018844 Text en © Akkurt et al. 2009 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 Akkurt, Mehmet Baktır, Zeliha Bogdanov, Milen G. Svinyarov, Ivan V. Büyükgüngör, Orhan (±)-trans-6,7-Dimethoxy-1-oxo-3-(2-thienyl)isochroman-4-carboxylic acid |
title | (±)-trans-6,7-Dimethoxy-1-oxo-3-(2-thienyl)isochroman-4-carboxylic acid |
title_full | (±)-trans-6,7-Dimethoxy-1-oxo-3-(2-thienyl)isochroman-4-carboxylic acid |
title_fullStr | (±)-trans-6,7-Dimethoxy-1-oxo-3-(2-thienyl)isochroman-4-carboxylic acid |
title_full_unstemmed | (±)-trans-6,7-Dimethoxy-1-oxo-3-(2-thienyl)isochroman-4-carboxylic acid |
title_short | (±)-trans-6,7-Dimethoxy-1-oxo-3-(2-thienyl)isochroman-4-carboxylic acid |
title_sort | (±)-trans-6,7-dimethoxy-1-oxo-3-(2-thienyl)isochroman-4-carboxylic acid |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2969835/ https://www.ncbi.nlm.nih.gov/pubmed/21583225 http://dx.doi.org/10.1107/S1600536809018844 |
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