Comparison of halogen bonding and van der Waals and π-π Inter-actions in 4,5-dibromo-2-hexyl-oxyphenol

Abstract

The title compound, C12H16BrO2, is an inter-esting case of a simple organic mol-ecule making use of five different types of intra- and inter-molecular inter-actions (viz. conventional and nonconventional hydrogen bonds, and π-π, Br⋯Br and Br⋯O contacts), all of them relevant in the mol-ecular and crystal structure geometry. The mol-ecules are strictly planar, with an intra-molecular O - H⋯O hydrogen bond, and associate into two-dimensional structures parallel to ( 01) through two different types of halogen bonding. The planar structures, in turn, stack parallel to each other inter-linked by C - H⋯π and π-π contacts. Also discussed are the relevant structural features leading to the rather low melting point of the compound.