Crystal structure of bis(3,5-dichloro-2-hydroxybenzyl)(2-methoxyethyl)amine

Abstract

The title compound, systematic name 4,4′,6,6′-tetrachloro-2,2′-{[(2-methoxyethyl)azanediyl]bis(methylene)}diphenol (C17H17Cl4NO, 1), was prepared via a modified Mannich reaction between 2-methoxyethylamine, 2,4-dichlorophenol, and aqueous formaldehyde. The resulting amine bis(phenol) provides an interesting comparison to related species as a result of the electron-withdrawing substituents on the phenol rings, in combination with similar steric parameters. One of the Cl atoms was modeled as a two-component disorder with partial occupancies of 0.49 (3) and 0.51 (3), while the pendant ether group was modeled as a two-component disorder with partial occupancies of 0.867 (3) and 0.133 (3). A comparison of metrical parameters for the title compound and closely related structures provides insight into the use of these species as ligands to support transition-metal complexes for applications as homogeneous catalysts.