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N,N′-(2,2′-Dithiodi-o-phenyl­ene)bis­(furan-2-carboxamide)

The reaction of 2,2′-dithio­bis(benzenamine) with furan-2-carbonyl chloride produced the bis-amide title compound, C(22)H(16)N(2)O(4)S(2), which, in the crystal, formed a helix; the structure consists of two planar furanoylbenzenamines related by an improper rotation of 96.3° about the S—S bond. The...

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Autores principales: Raftery, James, Lallbeeharry, Hiteyeshi, Bhowon, Minu G., Laulloo, Sabina J., Joule, John A.
Formato: Texto
Lenguaje:English
Publicado: International Union of Crystallography 2008
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2967937/
https://www.ncbi.nlm.nih.gov/pubmed/21581617
http://dx.doi.org/10.1107/S1600536808038828
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author Raftery, James
Lallbeeharry, Hiteyeshi
Bhowon, Minu G.
Laulloo, Sabina J.
Joule, John A.
author_facet Raftery, James
Lallbeeharry, Hiteyeshi
Bhowon, Minu G.
Laulloo, Sabina J.
Joule, John A.
author_sort Raftery, James
collection PubMed
description The reaction of 2,2′-dithio­bis(benzenamine) with furan-2-carbonyl chloride produced the bis-amide title compound, C(22)H(16)N(2)O(4)S(2), which, in the crystal, formed a helix; the structure consists of two planar furanoylbenzenamines related by an improper rotation of 96.3° about the S—S bond. The N-furanoylbenzenamine units are planar (maximum deviations = 0.316 and 0.132 Å). Each electron-deficient acyl­furan stacks (centroid–centroid separations of the two pairs of π–π stacked aromatic rings are 3.918 and 3.953 Å) with the electron-rich benzenamine of the other N-furan­oyl­benzenamine unit, leading to a spiral structure. The conformation is stabilized by two bifurcated intramolecular N—H⋯(O,S) interactions.
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spelling pubmed-29679372010-12-30 N,N′-(2,2′-Dithiodi-o-phenyl­ene)bis­(furan-2-carboxamide) Raftery, James Lallbeeharry, Hiteyeshi Bhowon, Minu G. Laulloo, Sabina J. Joule, John A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The reaction of 2,2′-dithio­bis(benzenamine) with furan-2-carbonyl chloride produced the bis-amide title compound, C(22)H(16)N(2)O(4)S(2), which, in the crystal, formed a helix; the structure consists of two planar furanoylbenzenamines related by an improper rotation of 96.3° about the S—S bond. The N-furanoylbenzenamine units are planar (maximum deviations = 0.316 and 0.132 Å). Each electron-deficient acyl­furan stacks (centroid–centroid separations of the two pairs of π–π stacked aromatic rings are 3.918 and 3.953 Å) with the electron-rich benzenamine of the other N-furan­oyl­benzenamine unit, leading to a spiral structure. The conformation is stabilized by two bifurcated intramolecular N—H⋯(O,S) interactions. International Union of Crystallography 2008-12-03 /pmc/articles/PMC2967937/ /pubmed/21581617 http://dx.doi.org/10.1107/S1600536808038828 Text en © Raftery 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
Raftery, James
Lallbeeharry, Hiteyeshi
Bhowon, Minu G.
Laulloo, Sabina J.
Joule, John A.
N,N′-(2,2′-Dithiodi-o-phenyl­ene)bis­(furan-2-carboxamide)
title N,N′-(2,2′-Dithiodi-o-phenyl­ene)bis­(furan-2-carboxamide)
title_full N,N′-(2,2′-Dithiodi-o-phenyl­ene)bis­(furan-2-carboxamide)
title_fullStr N,N′-(2,2′-Dithiodi-o-phenyl­ene)bis­(furan-2-carboxamide)
title_full_unstemmed N,N′-(2,2′-Dithiodi-o-phenyl­ene)bis­(furan-2-carboxamide)
title_short N,N′-(2,2′-Dithiodi-o-phenyl­ene)bis­(furan-2-carboxamide)
title_sort n,n′-(2,2′-dithiodi-o-phenyl­ene)bis­(furan-2-carboxamide)
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2967937/
https://www.ncbi.nlm.nih.gov/pubmed/21581617
http://dx.doi.org/10.1107/S1600536808038828
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