Crystal structures of p-substituted derivatives of 2,6-di­methyl­bromo­benzene with ½ ≤ Z′ ≤ 4

The crystal structures of four bromo­arenes based on 2,6-di­methyl­bromo­benzene are reported, which are differentiated according the functional group X placed para to the Br atom: X = CN (4-bromo-3,5-di­methyl­benzo­nitrile, C9H8BrN), (1), X = NO2 (2-bromo-1,3-dimethyl-5-nitro­benzene, C8H8BrNO2), (2), X = NH2 (4-bromo-3,5-di­methyl­aniline, C8H10BrN), (3) and X = OH (4-bromo-3,5-di­methyl­phenol, C8H9BrO), (4). The content of the asymmetric unit is different in each crystal, Z′ = ½ (X = CN), Z′ = 1 (X = NO2), Z′ = 2 (X = NH2), and Z′ = 4 (X = OH), and is related to the mol­ecular symmetry and the propensity of X to be involved in hydrogen bonding. In none of the studied compounds does the crystal structure feature other non-covalent inter­actions, such as π–π, C—H⋯π or C—Br⋯Br contacts.