Supramolecular organic frameworks derived from bromoaryl-substituted dichlorodiazabutadienes via Cl???Br halogen bonding

1-Aryl-3-(4-bromophenyl)-4,4-dichloro-1,2-diazabuta-1,3dienes were synthesized via copper-catalyzed reaction of 4-bromobenzaldehyde arylhydrazones with CCl4. X-ray diffraction analysis revealed non-covalent Cl???Br interactions in the crystalline state and formation of 3D supramolecular framework; DFT calculations and topological analysis of the electron density distribution within the framework of Bader?s theory (QTAIM method) confirmed these observations. Theoretical calculations showed that highly polarizable dichlorodiazadiene unit is capable of acting as a relatively strong halogen bond donor.