Interplay of Hydrogen and Halogen Bonding in the Crystal Structures of 2,6‐Dihalogenated Phenols

Hydrogen and halogen bonds are important anisotropic attractive interactions in the molecular crystalline state. 2,6-dibromophenol (1) was analyzed by single-crystal X-ray diffraction for first time. The intermolecular interaction pattern studied Hirshfeld surface analysis along with 2D fingerprint diagrams. characteristic that dominate crystal packing electrostatic type-II Br⋅⋅⋅Br interactions, O−H⋅⋅⋅O hydrogen bonds, an offset parallel π-stacking arrangement. Compound 1 compared 2,6-difluoro- (2) 2-bromo-6-chlorophenol (3) terms of their interplay between bonding. Whereas bond is more pronounced lighter homologues, halogen⋅⋅⋅halogen becomes a particularly directional, structure 2,6-dibromophenol.