Cargando…

Crystal structure of 2-{(R)-[1-(4-bromo­phen­yl)eth­yl]imino­meth­yl}-4-(phenyl­diazen­yl)phenol, a chiral photochromic Schiff base

The title chiral photochromic Schiff base compound, C(21)H(18)BrN(3)O, was synthesized from (R)-(+)-1-(4-bromo­phen­yl)ethyl­amine and the salicyl­aldehyde of an azo­benzene derivative. The mol­ecule corresponds to the phenol–imine tautomer, the C=N and N—C bond distances being 1.285 (3) and 1.470 (...

Descripción completa

Detalles Bibliográficos
Autores principales: Moriwaki, Ryoji, Akitsu, Takashiro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2015
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4645026/
https://www.ncbi.nlm.nih.gov/pubmed/26594580
http://dx.doi.org/10.1107/S2056989015019866
_version_ 1782400745214050304
author Moriwaki, Ryoji
Akitsu, Takashiro
author_facet Moriwaki, Ryoji
Akitsu, Takashiro
author_sort Moriwaki, Ryoji
collection PubMed
description The title chiral photochromic Schiff base compound, C(21)H(18)BrN(3)O, was synthesized from (R)-(+)-1-(4-bromo­phen­yl)ethyl­amine and the salicyl­aldehyde of an azo­benzene derivative. The mol­ecule corresponds to the phenol–imine tautomer, the C=N and N—C bond distances being 1.285 (3) and 1.470 (3) Å, respectively. The diazenyl group adopts a trans form, with an N=N distance of 1.256 (3) Å. The hy­droxy group is involved in intra­molecular O—H⋯N hydrogen bonding. In the crystal, C—H⋯π inter­actions consolidate the crystal packing of one-dimensional chains, which exhibits short inter­molecular Br⋯C contacts of 3.400 (3) Å.
format Online
Article
Text
id pubmed-4645026
institution National Center for Biotechnology Information
language English
publishDate 2015
publisher International Union of Crystallography
record_format MEDLINE/PubMed
spelling pubmed-46450262015-11-20 Crystal structure of 2-{(R)-[1-(4-bromo­phen­yl)eth­yl]imino­meth­yl}-4-(phenyl­diazen­yl)phenol, a chiral photochromic Schiff base Moriwaki, Ryoji Akitsu, Takashiro Acta Crystallogr E Crystallogr Commun Data Reports The title chiral photochromic Schiff base compound, C(21)H(18)BrN(3)O, was synthesized from (R)-(+)-1-(4-bromo­phen­yl)ethyl­amine and the salicyl­aldehyde of an azo­benzene derivative. The mol­ecule corresponds to the phenol–imine tautomer, the C=N and N—C bond distances being 1.285 (3) and 1.470 (3) Å, respectively. The diazenyl group adopts a trans form, with an N=N distance of 1.256 (3) Å. The hy­droxy group is involved in intra­molecular O—H⋯N hydrogen bonding. In the crystal, C—H⋯π inter­actions consolidate the crystal packing of one-dimensional chains, which exhibits short inter­molecular Br⋯C contacts of 3.400 (3) Å. International Union of Crystallography 2015-10-28 /pmc/articles/PMC4645026/ /pubmed/26594580 http://dx.doi.org/10.1107/S2056989015019866 Text en © Moriwaki and Akitsu 2015 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 Data Reports
Moriwaki, Ryoji
Akitsu, Takashiro
Crystal structure of 2-{(R)-[1-(4-bromo­phen­yl)eth­yl]imino­meth­yl}-4-(phenyl­diazen­yl)phenol, a chiral photochromic Schiff base
title Crystal structure of 2-{(R)-[1-(4-bromo­phen­yl)eth­yl]imino­meth­yl}-4-(phenyl­diazen­yl)phenol, a chiral photochromic Schiff base
title_full Crystal structure of 2-{(R)-[1-(4-bromo­phen­yl)eth­yl]imino­meth­yl}-4-(phenyl­diazen­yl)phenol, a chiral photochromic Schiff base
title_fullStr Crystal structure of 2-{(R)-[1-(4-bromo­phen­yl)eth­yl]imino­meth­yl}-4-(phenyl­diazen­yl)phenol, a chiral photochromic Schiff base
title_full_unstemmed Crystal structure of 2-{(R)-[1-(4-bromo­phen­yl)eth­yl]imino­meth­yl}-4-(phenyl­diazen­yl)phenol, a chiral photochromic Schiff base
title_short Crystal structure of 2-{(R)-[1-(4-bromo­phen­yl)eth­yl]imino­meth­yl}-4-(phenyl­diazen­yl)phenol, a chiral photochromic Schiff base
title_sort crystal structure of 2-{(r)-[1-(4-bromo­phen­yl)eth­yl]imino­meth­yl}-4-(phenyl­diazen­yl)phenol, a chiral photochromic schiff base
topic Data Reports
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4645026/
https://www.ncbi.nlm.nih.gov/pubmed/26594580
http://dx.doi.org/10.1107/S2056989015019866
work_keys_str_mv AT moriwakiryoji crystalstructureof2r14bromophenylethyliminomethyl4phenyldiazenylphenolachiralphotochromicschiffbase
AT akitsutakashiro crystalstructureof2r14bromophenylethyliminomethyl4phenyldiazenylphenolachiralphotochromicschiffbase