(E)-1-(4-Methoxyanthracen-1-yl)-2-phenyldiazene

Abstract

The title compound, C21H16N2O, has an E-conformation about the diazene N=N bond. It is reasonably planar with the phenyl ring being inclined to the mean plane of the anthracene moiety [planar to within 0.077 (3) Å] by 6.43 (10)°. The crystal structure is stabilized by C—H⋯π and weak π–π inter­actions [centroid–centroid distances of 3.7192 (16) and 3.8382 (15) Å], leading to the formation of two-dimensional networks stacking along [001] and lying parallel to (110).

Tautomerism in Azo and Azomethyne Dyes: When and If Theory Meets Experiment

“…Currently, structural data for the enol and keto tautomers of 1 are available in the literature [18] along with data for the fixed enol tautomer (OMe compound) of 6 [69]. In the case of compounds 2 – 5 even if crystallographic data are available the structures contain contribution of both tautomers [70,71], which makes the structural information unsuitable for benchmarking.…”