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Crystal structure of 2,4,6-tri­methyl­benzoic anhydride

The title compound, C(20)H(22)O(3), was formed in the reaction between 2,4,6-tri­methyl­benzoic acid and N,N-diiso­propyl­ethyl­amine in the presence of 1,3-di­chloro-1,3-bis­(di­methyl­amino)­propenium hydrogen dichloride, and was recrystallized from diethyl ether solution. It is the first exclusiv...

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Autores principales: Land, Michael A., Robertson, Katherine N., Clyburne, Jason A. C.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2017
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683502/
https://www.ncbi.nlm.nih.gov/pubmed/29152362
http://dx.doi.org/10.1107/S2056989017014670
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author Land, Michael A.
Robertson, Katherine N.
Clyburne, Jason A. C.
author_facet Land, Michael A.
Robertson, Katherine N.
Clyburne, Jason A. C.
author_sort Land, Michael A.
collection PubMed
description The title compound, C(20)H(22)O(3), was formed in the reaction between 2,4,6-tri­methyl­benzoic acid and N,N-diiso­propyl­ethyl­amine in the presence of 1,3-di­chloro-1,3-bis­(di­methyl­amino)­propenium hydrogen dichloride, and was recrystallized from diethyl ether solution. It is the first exclusively alkyl-substituted benzoic anhydride to have been structurally characterized. The asymmetric unit consists of a half mol­ecule, the other half of which is generated by twofold rotation symmetry; the dihedral angle between the symmetry-related aromatic rings is 54.97 (3)°. The geometric parameters of the aromatic ring are typical of those for 2,4,6-tri­methyl­phenyl substituted groups. The C=O and C—O bond lengths are 1.1934 (12) and 1.3958 (11) Å, respectively, and the angle between these three atoms (O=C—O) is 121.24 (9)°. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions. The packing features wavy chains that extend parallel to [001].
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spelling pubmed-56835022017-11-17 Crystal structure of 2,4,6-tri­methyl­benzoic anhydride Land, Michael A. Robertson, Katherine N. Clyburne, Jason A. C. Acta Crystallogr E Crystallogr Commun Research Communications The title compound, C(20)H(22)O(3), was formed in the reaction between 2,4,6-tri­methyl­benzoic acid and N,N-diiso­propyl­ethyl­amine in the presence of 1,3-di­chloro-1,3-bis­(di­methyl­amino)­propenium hydrogen dichloride, and was recrystallized from diethyl ether solution. It is the first exclusively alkyl-substituted benzoic anhydride to have been structurally characterized. The asymmetric unit consists of a half mol­ecule, the other half of which is generated by twofold rotation symmetry; the dihedral angle between the symmetry-related aromatic rings is 54.97 (3)°. The geometric parameters of the aromatic ring are typical of those for 2,4,6-tri­methyl­phenyl substituted groups. The C=O and C—O bond lengths are 1.1934 (12) and 1.3958 (11) Å, respectively, and the angle between these three atoms (O=C—O) is 121.24 (9)°. In the crystal, mol­ecules are linked by weak C—H⋯O hydrogen bonds and C—H⋯π inter­actions. The packing features wavy chains that extend parallel to [001]. International Union of Crystallography 2017-10-20 /pmc/articles/PMC5683502/ /pubmed/29152362 http://dx.doi.org/10.1107/S2056989017014670 Text en © Land et al. 2017 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/2.0/uk/
spellingShingle Research Communications
Land, Michael A.
Robertson, Katherine N.
Clyburne, Jason A. C.
Crystal structure of 2,4,6-tri­methyl­benzoic anhydride
title Crystal structure of 2,4,6-tri­methyl­benzoic anhydride
title_full Crystal structure of 2,4,6-tri­methyl­benzoic anhydride
title_fullStr Crystal structure of 2,4,6-tri­methyl­benzoic anhydride
title_full_unstemmed Crystal structure of 2,4,6-tri­methyl­benzoic anhydride
title_short Crystal structure of 2,4,6-tri­methyl­benzoic anhydride
title_sort crystal structure of 2,4,6-tri­methyl­benzoic anhydride
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5683502/
https://www.ncbi.nlm.nih.gov/pubmed/29152362
http://dx.doi.org/10.1107/S2056989017014670
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