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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 (...

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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
Descripción
Sumario: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.