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(E)-6,8-Dichloro-3-{[(naphthalen-1-ylmethyl)iminiumyl]methyl}-2H-chromen-4-olate
In the title compound, C(21)H(15)Cl(2)NO(2), the H atom of the –OH group is transferred to the N atom of the imine, forming a zwitterion. Thus, there is formation of a six-membered ring via an intramolecular O⋯H—N, rather than O—H⋯N, hydrogen bond in the molecule. The dihedral angle between the na...
Autores principales: | , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793731/ https://www.ncbi.nlm.nih.gov/pubmed/24109318 http://dx.doi.org/10.1107/S1600536813018084 |
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author | Ishikawa, Yoshinobu Motohashi, Yuya |
author_facet | Ishikawa, Yoshinobu Motohashi, Yuya |
author_sort | Ishikawa, Yoshinobu |
collection | PubMed |
description | In the title compound, C(21)H(15)Cl(2)NO(2), the H atom of the –OH group is transferred to the N atom of the imine, forming a zwitterion. Thus, there is formation of a six-membered ring via an intramolecular O⋯H—N, rather than O—H⋯N, hydrogen bond in the molecule. The dihedral angle between the naphthalene ring system and the benzene ring of the 2H-chromen system is 87.41 (4)°. In the crystal, the molecules are packed through N—H⋯O, π–π [centroid–centroid distances = 3.744 (3) and 3.780 (3) Å], C—Cl⋯π [Cl⋯centroid = 3.261 (3) Å], C—H⋯π and C—H⋯O interactions. |
format | Online Article Text |
id | pubmed-3793731 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-37937312013-10-09 (E)-6,8-Dichloro-3-{[(naphthalen-1-ylmethyl)iminiumyl]methyl}-2H-chromen-4-olate Ishikawa, Yoshinobu Motohashi, Yuya Acta Crystallogr Sect E Struct Rep Online Organic Papers In the title compound, C(21)H(15)Cl(2)NO(2), the H atom of the –OH group is transferred to the N atom of the imine, forming a zwitterion. Thus, there is formation of a six-membered ring via an intramolecular O⋯H—N, rather than O—H⋯N, hydrogen bond in the molecule. The dihedral angle between the naphthalene ring system and the benzene ring of the 2H-chromen system is 87.41 (4)°. In the crystal, the molecules are packed through N—H⋯O, π–π [centroid–centroid distances = 3.744 (3) and 3.780 (3) Å], C—Cl⋯π [Cl⋯centroid = 3.261 (3) Å], C—H⋯π and C—H⋯O interactions. International Union of Crystallography 2013-07-10 /pmc/articles/PMC3793731/ /pubmed/24109318 http://dx.doi.org/10.1107/S1600536813018084 Text en © Ishikawa and Motohashi 2013 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 Ishikawa, Yoshinobu Motohashi, Yuya (E)-6,8-Dichloro-3-{[(naphthalen-1-ylmethyl)iminiumyl]methyl}-2H-chromen-4-olate |
title | (E)-6,8-Dichloro-3-{[(naphthalen-1-ylmethyl)iminiumyl]methyl}-2H-chromen-4-olate |
title_full | (E)-6,8-Dichloro-3-{[(naphthalen-1-ylmethyl)iminiumyl]methyl}-2H-chromen-4-olate |
title_fullStr | (E)-6,8-Dichloro-3-{[(naphthalen-1-ylmethyl)iminiumyl]methyl}-2H-chromen-4-olate |
title_full_unstemmed | (E)-6,8-Dichloro-3-{[(naphthalen-1-ylmethyl)iminiumyl]methyl}-2H-chromen-4-olate |
title_short | (E)-6,8-Dichloro-3-{[(naphthalen-1-ylmethyl)iminiumyl]methyl}-2H-chromen-4-olate |
title_sort | (e)-6,8-dichloro-3-{[(naphthalen-1-ylmethyl)iminiumyl]methyl}-2h-chromen-4-olate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3793731/ https://www.ncbi.nlm.nih.gov/pubmed/24109318 http://dx.doi.org/10.1107/S1600536813018084 |
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