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2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate
In the title compound, C(16)H(15)N(2) (+)·C(6)H(4)BrO(3)S(−), the cation exists in the E configuration and is essentially planar with a dihedral angle of 3.10 (5)° between the pyridinium ring and the indole ring system. The π-conjugated planes of the cation and the anion are inclined to each other a...
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/PMC2977651/ https://www.ncbi.nlm.nih.gov/pubmed/21583994 http://dx.doi.org/10.1107/S1600536809011386 |
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author | Chantrapromma, Suchada Kobkeatthawin, Thawanrat Fun, Hoong-Kun |
author_facet | Chantrapromma, Suchada Kobkeatthawin, Thawanrat Fun, Hoong-Kun |
author_sort | Chantrapromma, Suchada |
collection | PubMed |
description | In the title compound, C(16)H(15)N(2) (+)·C(6)H(4)BrO(3)S(−), the cation exists in the E configuration and is essentially planar with a dihedral angle of 3.10 (5)° between the pyridinium ring and the indole ring system. The π-conjugated planes of the cation and the anion are inclined to each other at a dihedral angle of 64.32 (4)°. In the crystal structure, the cations are stacked in an antiparallel manner along the a axis. The anions are linked into a chain along the a axis. The cations and the anions are linked into a three-dimensional network by N—H⋯O and weak C—H⋯O hydrogen bonds. The crystal structure is further stabilized by C—H⋯π interactions. A π–π interaction between the five-membered heterocyclic ring of the indole system and the pyridinium ring is also observed with a centroid–centroid distance of 3.5855 (7) Å. |
format | Text |
id | pubmed-2977651 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2009 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-29776512010-12-30 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate Chantrapromma, Suchada Kobkeatthawin, Thawanrat 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)BrO(3)S(−), the cation exists in the E configuration and is essentially planar with a dihedral angle of 3.10 (5)° between the pyridinium ring and the indole ring system. The π-conjugated planes of the cation and the anion are inclined to each other at a dihedral angle of 64.32 (4)°. In the crystal structure, the cations are stacked in an antiparallel manner along the a axis. The anions are linked into a chain along the a axis. The cations and the anions are linked into a three-dimensional network by N—H⋯O and weak C—H⋯O hydrogen bonds. The crystal structure is further stabilized by C—H⋯π interactions. A π–π interaction between the five-membered heterocyclic ring of the indole system and the pyridinium ring is also observed with a centroid–centroid distance of 3.5855 (7) Å. International Union of Crystallography 2009-04-02 /pmc/articles/PMC2977651/ /pubmed/21583994 http://dx.doi.org/10.1107/S1600536809011386 Text en © Chantrapromma 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 Chantrapromma, Suchada Kobkeatthawin, Thawanrat Fun, Hoong-Kun 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate |
title | 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate
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title_full | 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate
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title_fullStr | 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate
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title_full_unstemmed | 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate
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title_short | 2-[(E)-2-(1H-Indol-3-yl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate
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title_sort | 2-[(e)-2-(1h-indol-3-yl)ethenyl]-1-methylpyridinium 4-bromobenzenesulfonate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2977651/ https://www.ncbi.nlm.nih.gov/pubmed/21583994 http://dx.doi.org/10.1107/S1600536809011386 |
work_keys_str_mv | AT chantraprommasuchada 2e21hindol3ylethenyl1methylpyridinium4bromobenzenesulfonate AT kobkeatthawinthawanrat 2e21hindol3ylethenyl1methylpyridinium4bromobenzenesulfonate AT funhoongkun 2e21hindol3ylethenyl1methylpyridinium4bromobenzenesulfonate |