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2-Amino-6-[(2,6-dichloro­phen­yl)imino]-3-oxocyclo­hexa-1,4-dienecarbaldehyde

The title compound, C(13)H(8)Cl(2)N(2)O(2), was obtained by the oxidation of diclofenac {systematic name: 2-[2-(2,6-dichloro­phenyl­amino)­phen­yl]acetic acid}, an anti-inflammatory drug, with hydrogen peroxide catalysed by chlorido[5,10,15,20-tetra­kis­(2,6-dichloro­phen­yl)porphyrinato]manganese(I...

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Autores principales: Neves, Cláudia M. B., Fernandes, José A., Simões, Mário M. Q., Neves, M. Graça P. M. S., Cavaleiro, José A. S., Almeida Paz, Filipe A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247420/
https://www.ncbi.nlm.nih.gov/pubmed/22220038
http://dx.doi.org/10.1107/S1600536811042619
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author Neves, Cláudia M. B.
Fernandes, José A.
Simões, Mário M. Q.
Neves, M. Graça P. M. S.
Cavaleiro, José A. S.
Almeida Paz, Filipe A.
author_facet Neves, Cláudia M. B.
Fernandes, José A.
Simões, Mário M. Q.
Neves, M. Graça P. M. S.
Cavaleiro, José A. S.
Almeida Paz, Filipe A.
author_sort Neves, Cláudia M. B.
collection PubMed
description The title compound, C(13)H(8)Cl(2)N(2)O(2), was obtained by the oxidation of diclofenac {systematic name: 2-[2-(2,6-dichloro­phenyl­amino)­phen­yl]acetic acid}, an anti-inflammatory drug, with hydrogen peroxide catalysed by chlorido[5,10,15,20-tetra­kis­(2,6-dichloro­phen­yl)porphyrinato]manganese(III), using ammonium acetate as co-catalyst. The asymmetric unit contains two crystallographically independent mol­ecules of the title compound (Z′ = 2). The close packing of individual mol­ecules is mediated by a series of strong and rather directional N—H⋯Cl and N—H⋯O hydrogen bonds, plus weak π–π [distance between the individual double bonds of symmetry-related imino­quinone rings = 3.7604 (13) Å] and Cl⋯O inter­actions [3.0287 (18) Å].
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spelling pubmed-32474202012-01-04 2-Amino-6-[(2,6-dichloro­phen­yl)imino]-3-oxocyclo­hexa-1,4-dienecarbaldehyde Neves, Cláudia M. B. Fernandes, José A. Simões, Mário M. Q. Neves, M. Graça P. M. S. Cavaleiro, José A. S. Almeida Paz, Filipe A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(13)H(8)Cl(2)N(2)O(2), was obtained by the oxidation of diclofenac {systematic name: 2-[2-(2,6-dichloro­phenyl­amino)­phen­yl]acetic acid}, an anti-inflammatory drug, with hydrogen peroxide catalysed by chlorido[5,10,15,20-tetra­kis­(2,6-dichloro­phen­yl)porphyrinato]manganese(III), using ammonium acetate as co-catalyst. The asymmetric unit contains two crystallographically independent mol­ecules of the title compound (Z′ = 2). The close packing of individual mol­ecules is mediated by a series of strong and rather directional N—H⋯Cl and N—H⋯O hydrogen bonds, plus weak π–π [distance between the individual double bonds of symmetry-related imino­quinone rings = 3.7604 (13) Å] and Cl⋯O inter­actions [3.0287 (18) Å]. International Union of Crystallography 2011-10-22 /pmc/articles/PMC3247420/ /pubmed/22220038 http://dx.doi.org/10.1107/S1600536811042619 Text en © Neves et al. 2011 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
Neves, Cláudia M. B.
Fernandes, José A.
Simões, Mário M. Q.
Neves, M. Graça P. M. S.
Cavaleiro, José A. S.
Almeida Paz, Filipe A.
2-Amino-6-[(2,6-dichloro­phen­yl)imino]-3-oxocyclo­hexa-1,4-dienecarbaldehyde
title 2-Amino-6-[(2,6-dichloro­phen­yl)imino]-3-oxocyclo­hexa-1,4-dienecarbaldehyde
title_full 2-Amino-6-[(2,6-dichloro­phen­yl)imino]-3-oxocyclo­hexa-1,4-dienecarbaldehyde
title_fullStr 2-Amino-6-[(2,6-dichloro­phen­yl)imino]-3-oxocyclo­hexa-1,4-dienecarbaldehyde
title_full_unstemmed 2-Amino-6-[(2,6-dichloro­phen­yl)imino]-3-oxocyclo­hexa-1,4-dienecarbaldehyde
title_short 2-Amino-6-[(2,6-dichloro­phen­yl)imino]-3-oxocyclo­hexa-1,4-dienecarbaldehyde
title_sort 2-amino-6-[(2,6-dichloro­phen­yl)imino]-3-oxocyclo­hexa-1,4-dienecarbaldehyde
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3247420/
https://www.ncbi.nlm.nih.gov/pubmed/22220038
http://dx.doi.org/10.1107/S1600536811042619
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