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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...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2011
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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. |
format | Online Article Text |
id | pubmed-3254566 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2011 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
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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