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Crystal structure of 2-{(R)-[1-(4-bromo-phen-yl)eth-yl]imino-meth-yl}-4-(phenyl-diazen-yl)phenol, a chiral photochromic Schiff base.


ABSTRACT: The title chiral photochromic Schiff base compound, C21H18BrN3O, was synthesized from (R)-(+)-1-(4-bromo-phen-yl)ethyl-amine and the salicyl-aldehyde of an azo-benzene derivative. The mol-ecule 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 hy-droxy group is involved in intra-molecular O-H?N hydrogen bonding. In the crystal, C-H?? inter-actions consolidate the crystal packing of one-dimensional chains, which exhibits short inter-molecular Br?C contacts of 3.400?(3)?Å.

SUBMITTER: Moriwaki R 

PROVIDER: S-EPMC4645026 | biostudies-literature | 2015 Nov

REPOSITORIES: biostudies-literature

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Crystal structure of 2-{(R)-[1-(4-bromo-phen-yl)eth-yl]imino-meth-yl}-4-(phenyl-diazen-yl)phenol, a chiral photochromic Schiff base.

Moriwaki Ryoji R   Akitsu Takashiro T  

Acta crystallographica. Section E, Crystallographic communications 20151028 Pt 11


The title chiral photochromic Schiff base compound, C21H18BrN3O, was synthesized from (R)-(+)-1-(4-bromo-phen-yl)ethyl-amine and the salicyl-aldehyde of an azo-benzene derivative. The mol-ecule 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 hy-droxy group is involved in intra-molecular O-H⋯N hydrogen bonding. In the crystal, C-H⋯π inter-actions  ...[more]

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