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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...

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Autores principales: Akkurt, Mehmet, Baktır, Zeliha, Bogdanov, Milen G., Svinyarov, Ivan V., Büyükgüngör, Orhan
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2009
Materias:
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.
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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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