Dibromomethyl- and bromomethyl- or bromo-substituted benzenes and naphthalenes: C-Br...Br interactions.

The structures of six benzene and three naphthalene derivatives involving bromo, bromomethyl and dibromomethyl substituents, namely, 1,3-dibromo-5-(dibromomethyl)benzene, C 7 H 4 Br 4 , 1,4-dibromo-2,5-bis(bromomethyl)benzene, C 8 H 4 Br 6 , 1,4-dibromo-2-(dibromomethyl)benzene, C 7 H 4 Br 4 , 1,2-bis(dibromomethyl)benzene, C 8 H 6 Br 4 , 1-(bromomethyl)-2-(dibromomethyl)benzene, C 8 H 7 Br 3 , 2-(bromomethyl)-3-(dibromomethyl)naphthalene, C 12 H 9 Br 3 , 2,3-bis(dibromomethyl)naphthalene, C 12 H 8 Br 4 , 1-(bromomethyl)-2-(dibromomethyl)naphthalene, C 12 H 9 Br 3 , and 1,3-bis(dibromomethyl)benzene, C 8 H 6 Br 4 , are presented. The packing patterns of these compounds are dominated by Br...Br contacts and C-H...Br hydrogen bonds. The Br...Br contacts, shorter than twice the van der Waals radius of bromine (3.7 Å), seem to play a crucial role in the crystal packing of all these compounds. The occurrence of Type I and Type II interactions is also discussed briefly, considering the effective atomic radius of bromine, as is their impact on the packing of molecules in the individual structures.