Abstract
The title compound {systematic name: 2-hy-droxy-5-[2-(2,4,6-tri-bromo-phen-yl)diazen-1-yl]cyclo-hepta-2,4,6-trien-1-one}, C13H7Br3N2O2, is essentially planar, with an r.m.s. deviation of 0.054 Å. The mol-ecular structure is fixed in the azo tautomer by intra-molecular C-H⋯N inter-actions, with O-H⋯O hydrogen bonds creating linked dimers. Charge-transfer inter-actions are observed, with the segregated stacks linked by Br⋯Br inter-actions.
Highlights
The title compound {systematic name: 2-hydroxy-5-[2-(2,4,6-tribromophenyl)diazen-1-yl]cyclohepta-2,4,6-trien-1-one}, C13H7Br3N2O2, is essentially planar, with an r.m.s. deviation of 0.054 A
As part of this study, we report the crystal structure of the title compound, I (Fig. 1)
The title compound, I, shows no signs of azo-hydrazone tautomerization, a phenomenon known to the phenylazoderivatives, because of the stabilizing intramolecular interaction of the hydrogen (H6) atom of the tropolone ring with the nitrogen (N2) atom of the azo group (Table 1, Fig. 2)
Summary
Dyes have become an enormous market (approx. $13.4 billion) with over one million tons of various dyes and pigments being produced each year, and their uses ranging from textiles, cosmetics, food coloring, printing inks to optical recording media. $13.4 billion) with over one million tons of various dyes and pigments being produced each year, and their uses ranging from textiles, cosmetics, food coloring, printing inks to optical recording media. Azo dyes form one of the largest groups of synthetic chemical dyes with the chemical structure of these compounds featuring substituted aromatic rings that are joined by one or more azo groups (R—N N—R). The first of these dyes to be produced was aniline yellow, which contains an azo-substituted benzene group. Tropolone exhibits similar aromatic properties to benzene; as such, a study was undertaken to synthesize a series of azo-functionalized tropolones. As part of this study, we report the crystal structure of the title compound, I (Fig. 1)
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