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2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)-2-cyano­acetamide

Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)propane­dial with hydroxyl­amine gives the title compound, C(14)H(14)ClN(3)O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyano­acryl­amide unit...

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Autores principales: Helliwell, Madeleine, Baradarani, Mehdi M., Alyari, Maryam, Afghan, Arash, Joule, John 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/PMC3254566/
https://www.ncbi.nlm.nih.gov/pubmed/22259516
http://dx.doi.org/10.1107/S1600536811053918
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author Helliwell, Madeleine
Baradarani, Mehdi M.
Alyari, Maryam
Afghan, Arash
Joule, John A.
author_facet Helliwell, Madeleine
Baradarani, Mehdi M.
Alyari, Maryam
Afghan, Arash
Joule, John A.
author_sort Helliwell, Madeleine
collection PubMed
description Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)propane­dial with hydroxyl­amine gives the title compound, C(14)H(14)ClN(3)O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyano­acryl­amide unit. The orientation of the acetamide group arises from intra­molecular hydrogen bonding between the indole N—H and carbonyl groups. In the crystal, inversion-related acetamide groups form N—H⋯O hydrogen-bonded dimers in graph-set R (2) (2)(8) motifs, whilst dimers are also formed by pairs of amine–nitrile N—H⋯N hydrogen bonds in R (2) (2)(12) motifs. These inter­actions together generate ribbons that propagate along the b-axis direction.
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spelling pubmed-32545662012-01-18 2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)-2-cyano­acetamide Helliwell, Madeleine Baradarani, Mehdi M. Alyari, Maryam Afghan, Arash Joule, John A. Acta Crystallogr Sect E Struct Rep Online Organic Papers Reaction of 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)propane­dial with hydroxyl­amine gives the title compound, C(14)H(14)ClN(3)O, in which the ring N atom is essentially planar [sum of angles around the ring N atom = 361°], indicating conjugation with the 2-cyano­acryl­amide unit. The orientation of the acetamide group arises from intra­molecular hydrogen bonding between the indole N—H and carbonyl groups. In the crystal, inversion-related acetamide groups form N—H⋯O hydrogen-bonded dimers in graph-set R (2) (2)(8) motifs, whilst dimers are also formed by pairs of amine–nitrile N—H⋯N hydrogen bonds in R (2) (2)(12) motifs. These inter­actions together generate ribbons that propagate along the b-axis direction. International Union of Crystallography 2011-12-23 /pmc/articles/PMC3254566/ /pubmed/22259516 http://dx.doi.org/10.1107/S1600536811053918 Text en © Helliwell et al. 2012 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
Helliwell, Madeleine
Baradarani, Mehdi M.
Alyari, Maryam
Afghan, Arash
Joule, John A.
2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)-2-cyano­acetamide
title 2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)-2-cyano­acetamide
title_full 2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)-2-cyano­acetamide
title_fullStr 2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)-2-cyano­acetamide
title_full_unstemmed 2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)-2-cyano­acetamide
title_short 2-(4-Chloro-3,3,7-trimethyl-2,3-dihydro-1H-indol-2-yl­idene)-2-cyano­acetamide
title_sort 2-(4-chloro-3,3,7-trimethyl-2,3-dihydro-1h-indol-2-yl­idene)-2-cyano­acetamide
topic Organic Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3254566/
https://www.ncbi.nlm.nih.gov/pubmed/22259516
http://dx.doi.org/10.1107/S1600536811053918
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