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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...

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Detalles Bibliográficos
Autores principales: Ishikawa, Yoshinobu, Motohashi, Yuya
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2013
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.
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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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