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Ethyl 1-acetyl-1H-indole-3-carboxylate
The title compound, C(13)H(13)NO(3), was synthesized by acetylation of ethyl 1H-indole-3-carboxylate. The aromatic ring system of the molecule is essentially planar, but the saturated ethyl group is also located within this plane and the overall r.m.s. deviation from planarity is only 0.034 Å. Pa...
Autores principales: | , , , , |
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Formato: | Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977149/ https://www.ncbi.nlm.nih.gov/pubmed/21583507 http://dx.doi.org/10.1107/S1600536809025379 |
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author | Siddiquee, Tasneem Islam, Shahid Bennett, Dennis Zeller, Matthias Hossain, Mahmun |
author_facet | Siddiquee, Tasneem Islam, Shahid Bennett, Dennis Zeller, Matthias Hossain, Mahmun |
author_sort | Siddiquee, Tasneem |
collection | PubMed |
description | The title compound, C(13)H(13)NO(3), was synthesized by acetylation of ethyl 1H-indole-3-carboxylate. The aromatic ring system of the molecule is essentially planar, but the saturated ethyl group is also located within this plane and the overall r.m.s. deviation from planarity is only 0.034 Å. Pairs of C—H⋯O interactions connect molecules into chains along the diagonal of the unit cell. Molecules also form weakly connected dimers via π⋯π stacking interactions of the indole rings with centroid–centroid separations of 3.571 (1) Å. C—H⋯π interactions between methylene and methyl groups and the indole and benzene ring complete the directional intermolecular interactions found in the crystal structure. |
format | Text |
id | pubmed-2977149 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29771492010-12-30 Ethyl 1-acetyl-1H-indole-3-carboxylate Siddiquee, Tasneem Islam, Shahid Bennett, Dennis Zeller, Matthias Hossain, Mahmun Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound, C(13)H(13)NO(3), was synthesized by acetylation of ethyl 1H-indole-3-carboxylate. The aromatic ring system of the molecule is essentially planar, but the saturated ethyl group is also located within this plane and the overall r.m.s. deviation from planarity is only 0.034 Å. Pairs of C—H⋯O interactions connect molecules into chains along the diagonal of the unit cell. Molecules also form weakly connected dimers via π⋯π stacking interactions of the indole rings with centroid–centroid separations of 3.571 (1) Å. C—H⋯π interactions between methylene and methyl groups and the indole and benzene ring complete the directional intermolecular interactions found in the crystal structure. International Union of Crystallography 2009-07-08 /pmc/articles/PMC2977149/ /pubmed/21583507 http://dx.doi.org/10.1107/S1600536809025379 Text en © Siddiquee 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 Siddiquee, Tasneem Islam, Shahid Bennett, Dennis Zeller, Matthias Hossain, Mahmun Ethyl 1-acetyl-1H-indole-3-carboxylate |
title | Ethyl 1-acetyl-1H-indole-3-carboxylate |
title_full | Ethyl 1-acetyl-1H-indole-3-carboxylate |
title_fullStr | Ethyl 1-acetyl-1H-indole-3-carboxylate |
title_full_unstemmed | Ethyl 1-acetyl-1H-indole-3-carboxylate |
title_short | Ethyl 1-acetyl-1H-indole-3-carboxylate |
title_sort | ethyl 1-acetyl-1h-indole-3-carboxylate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977149/ https://www.ncbi.nlm.nih.gov/pubmed/21583507 http://dx.doi.org/10.1107/S1600536809025379 |
work_keys_str_mv | AT siddiqueetasneem ethyl1acetyl1hindole3carboxylate AT islamshahid ethyl1acetyl1hindole3carboxylate AT bennettdennis ethyl1acetyl1hindole3carboxylate AT zellermatthias ethyl1acetyl1hindole3carboxylate AT hossainmahmun ethyl1acetyl1hindole3carboxylate |