Supramolecular patterns in the crystal structures of 1,3,5-trisubstituted 2,4,6-triethylbenzenes bearing halogenophenoxy groups

Abstract

X-ray structure analysis of a series of 1,3,5-trisubstituted 2,4,6-triethylbenzene derivatives, the structures of which differ in the nature, position and number of halogen atoms attached to the arene rings of the functionalized side-arms, provide information about how these structural differences affect the modes of molecular interactions and the conformations of the tripodal molecules. The crystal structures are characterized by the presence of dimers, which are constructed differently for compounds 1–6 than for 7, the only compound with ortho-substituted halogenophenoxy groups. Compounds 1–6 show an aab arrangement of the halogenophenoxy groups and a pronounced tendency to form pairs of closely nested molecules held together by C–H⋯O and/or C–H⋯π interactions. In the case of compound 7, which adopts the aaa orientation of the functionalized side-arms, the dimeric structures are stabilized by Br⋯Br and Br⋯O interactions. The association of the molecular dimers of 1–7 occurs via halogen bonds (Hal⋯Hal and Hal⋯π) and C–H⋯Hal hydrogen bonds.