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, C7H4Br4, 1,4‐dibromo‐2,5‐bis(bromomethyl)benzene, C8H4Br6, 1,4‐dibromo‐2‐(dibromomethyl)benzene, C7H4Br4, 1,2‐bis(dibromomethyl)benzene, C8H6Br4, 1‐(bromomethyl)‐2‐(dibromomethyl)benzene, C8H7Br3, 2‐(bromomethyl)‐3‐(dibromomethyl)naphthalene, C12H9Br3, 2,3‐bis(dibromomethyl)naphthalene, C12H8Br4, 1‐(bromomethyl)‐2‐(dibromomethyl)naphthalene, C12H9Br3, and 1,3‐bis(dibromomethyl)benzene, C8H6Br4, 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. [ABSTRACT FROM AUTHOR]