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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...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2007
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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)°]. |
format | Text |
id | pubmed-2915231 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2007 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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