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3-[(Z)-(4-Diethyl­amino-6-oxocyclo­hexa-2,4-dien-1-yl­idene)methyl­amino]benzoic acid

The title compound, C(18)H(20)N(2)O(3), crystallizes as the keto tautomer, unlike the vast majority of similar structures that have been reported that contain the hydr­oxy tautomer. There are two strong hydrogen bonds in the crystal structure, both accepted by the same carbonyl group: one intra­mole...

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Autores principales: Swamy, M. T., Narayana, B., Yathirajan, H. S., Sarojini, B. K., Kubicki, Maciej
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2007
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2915231/
https://www.ncbi.nlm.nih.gov/pubmed/21200729
http://dx.doi.org/10.1107/S1600536807064446
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author Swamy, M. T.
Narayana, B.
Yathirajan, H. S.
Sarojini, B. K.
Kubicki, Maciej
author_facet Swamy, M. T.
Narayana, B.
Yathirajan, H. S.
Sarojini, B. K.
Kubicki, Maciej
author_sort Swamy, M. T.
collection PubMed
description The title compound, C(18)H(20)N(2)O(3), crystallizes as the keto tautomer, unlike the vast majority of similar structures that have been reported that contain the hydr­oxy tautomer. There are two strong hydrogen bonds in the crystal structure, both accepted by the same carbonyl group: one intra­molecular N—H⋯O and one inter­molecular O—H⋯O. As a result, the carbonyl C=O distance is long, at 1.310 (2) Å, which may suggest the mol­ecule has a significant zwitterionic character. The dihedral angle between the benzene ring planes is 15.05 (7)°. As a result of the intramolecular hydrogen bond, the bridging C—C=N—C group is almost coplanar with the benzene ring that has the diethylamino substituent [dihedral angle 2.35 (15)°].
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spelling pubmed-29152312010-12-30 3-[(Z)-(4-Diethyl­amino-6-oxocyclo­hexa-2,4-dien-1-yl­idene)methyl­amino]benzoic acid Swamy, M. T. Narayana, B. Yathirajan, H. S. Sarojini, B. K. Kubicki, Maciej Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(18)H(20)N(2)O(3), crystallizes as the keto tautomer, unlike the vast majority of similar structures that have been reported that contain the hydr­oxy tautomer. There are two strong hydrogen bonds in the crystal structure, both accepted by the same carbonyl group: one intra­molecular N—H⋯O and one inter­molecular O—H⋯O. As a result, the carbonyl C=O distance is long, at 1.310 (2) Å, which may suggest the mol­ecule has a significant zwitterionic character. The dihedral angle between the benzene ring planes is 15.05 (7)°. As a result of the intramolecular hydrogen bond, the bridging C—C=N—C group is almost coplanar with the benzene ring that has the diethylamino substituent [dihedral angle 2.35 (15)°]. International Union of Crystallography 2007-12-06 /pmc/articles/PMC2915231/ /pubmed/21200729 http://dx.doi.org/10.1107/S1600536807064446 Text en © International Union of Crystallography 2008 http://journals.iucr.org/services/termsofuse.html This is an open-access article distributed under the terms described at http://journals.iucr.org/services/termsofuse.html.
spellingShingle Organic Papers
Swamy, M. T.
Narayana, B.
Yathirajan, H. S.
Sarojini, B. K.
Kubicki, Maciej
3-[(Z)-(4-Diethyl­amino-6-oxocyclo­hexa-2,4-dien-1-yl­idene)methyl­amino]benzoic acid
title 3-[(Z)-(4-Diethyl­amino-6-oxocyclo­hexa-2,4-dien-1-yl­idene)methyl­amino]benzoic acid
title_full 3-[(Z)-(4-Diethyl­amino-6-oxocyclo­hexa-2,4-dien-1-yl­idene)methyl­amino]benzoic acid
title_fullStr 3-[(Z)-(4-Diethyl­amino-6-oxocyclo­hexa-2,4-dien-1-yl­idene)methyl­amino]benzoic acid
title_full_unstemmed 3-[(Z)-(4-Diethyl­amino-6-oxocyclo­hexa-2,4-dien-1-yl­idene)methyl­amino]benzoic acid
title_short 3-[(Z)-(4-Diethyl­amino-6-oxocyclo­hexa-2,4-dien-1-yl­idene)methyl­amino]benzoic acid
title_sort 3-[(z)-(4-diethyl­amino-6-oxocyclo­hexa-2,4-dien-1-yl­idene)methyl­amino]benzoic acid
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2915231/
https://www.ncbi.nlm.nih.gov/pubmed/21200729
http://dx.doi.org/10.1107/S1600536807064446
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