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2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-chlorobenzenesulfonate
In the title compound, C(16)H(15)N(2) (+)·C(6)H(4)ClO(3)S(−), the cation exists in an E configuration with respect to the central C=C bond and is approximately planar, with a dihedral angle of 2.95 (5)° between the pyridinium and indole rings. The mean plane of the π-conjugated system of the cation...
Autores principales: | , , |
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Formato: | Texto |
Lenguaje: | English |
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International Union of Crystallography
2009
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977504/ https://www.ncbi.nlm.nih.gov/pubmed/21583709 http://dx.doi.org/10.1107/S1600536809029547 |
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author | Kobkeatthawin, Thawanrat Chantrapromma, Suchada Fun, Hoong-Kun |
author_facet | Kobkeatthawin, Thawanrat Chantrapromma, Suchada Fun, Hoong-Kun |
author_sort | Kobkeatthawin, Thawanrat |
collection | PubMed |
description | In the title compound, C(16)H(15)N(2) (+)·C(6)H(4)ClO(3)S(−), the cation exists in an E configuration with respect to the central C=C bond and is approximately planar, with a dihedral angle of 2.95 (5)° between the pyridinium and indole rings. The mean plane of the π-conjugated system of the cation and the benzene ring of the anion are inclined to each other at a dihedral angle of 69.65 (4)°. In the crystal packing, the cations are stacked in an antiparallel manner along the a axis, resulting in a π–π interaction with a centroid–centroid distance of 3.5889 (7) Å. The anions are linked into a chain along the a axis by weak C—H⋯O interactions. The cations are linked with the anions into a three-dimensional network by N—H⋯O hydrogen bonds and weak C—H⋯O interactions. There are also short O⋯Cl [3.1272 (10) Å] and C⋯O [3.1432 (14)–3.3753 (14) Å] contacts. The crystal structure is further stabilized by C—H⋯π interactions. |
format | Text |
id | pubmed-2977504 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29775042010-12-30 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-chlorobenzenesulfonate Kobkeatthawin, Thawanrat Chantrapromma, Suchada Fun, Hoong-Kun Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(16)H(15)N(2) (+)·C(6)H(4)ClO(3)S(−), the cation exists in an E configuration with respect to the central C=C bond and is approximately planar, with a dihedral angle of 2.95 (5)° between the pyridinium and indole rings. The mean plane of the π-conjugated system of the cation and the benzene ring of the anion are inclined to each other at a dihedral angle of 69.65 (4)°. In the crystal packing, the cations are stacked in an antiparallel manner along the a axis, resulting in a π–π interaction with a centroid–centroid distance of 3.5889 (7) Å. The anions are linked into a chain along the a axis by weak C—H⋯O interactions. The cations are linked with the anions into a three-dimensional network by N—H⋯O hydrogen bonds and weak C—H⋯O interactions. There are also short O⋯Cl [3.1272 (10) Å] and C⋯O [3.1432 (14)–3.3753 (14) Å] contacts. The crystal structure is further stabilized by C—H⋯π interactions. International Union of Crystallography 2009-07-31 /pmc/articles/PMC2977504/ /pubmed/21583709 http://dx.doi.org/10.1107/S1600536809029547 Text en © Kobkeatthawin 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 Kobkeatthawin, Thawanrat Chantrapromma, Suchada Fun, Hoong-Kun 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-chlorobenzenesulfonate |
title | 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-chlorobenzenesulfonate
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title_full | 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-chlorobenzenesulfonate
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title_fullStr | 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-chlorobenzenesulfonate
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title_full_unstemmed | 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-chlorobenzenesulfonate
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title_short | 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-chlorobenzenesulfonate
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title_sort | 2-[(e)-2-(1h-indol-3-yl)ethenyl]-1-methylpyridinium 4-chlorobenzenesulfonate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977504/ https://www.ncbi.nlm.nih.gov/pubmed/21583709 http://dx.doi.org/10.1107/S1600536809029547 |
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