| Summary: | We have prepared and characterized 1,4-dibromo-2,5-bis(2-phenylethoxy)benzene (<b>1</b>) and 1,4-dibromo-2,5-bis(3-phenylpropoxy)benzene (<b>2</b>). Their single-crystal structures confirm that, at the molecular level, they are similar with the phenylalkoxy chains in extended conformations. However, there are significant differences in packing interactions. The packing in <b>1</b> is dominated by C–Br...π(arene) interactions, with each Br located over one C–C bond of the central arene ring of an adjacent molecule. In contrast, the packing of molecules of <b>2</b> involves a combination of C–H...Br hydrogen bonds, Br...Br interactions, and arene–arene π-stacking. The single-crystal structures of both orthorhombic and triclinic polymorphs of <b>1</b> have been determined and the packing interactions are shown to be essentially identical.
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