Role of Halogen Substituents on Halogen Bonding in 4,5-DiBromohexahydro-3a,6-Epoxyisoindol-1(4H)-ones

A series of 4,5-dibromo-2-(4-substituted phenyl)hexahydro-3a,6-epoxyisoindol-1(4H)-ones were synthesized by reaction the corresponding 2-(4-substituted phenyl)-2,3,7,7a-tetrahydro-3a,6-epoxyisoindol-1(6H)-ones with [(Me2NCOMe)2H]Br3 in dry chloroform under reflux for 3−5 h. In contrast to 4-F and 4-Cl substituents, one bromine atoms isoindole moiety behaves as a halogen bond donor formation intermolecular bonding 4-H, 4-Br 4-I analogues. Not only hydrogen bonds, but also Ha⋯Ha Ha⋯π types bonds 4-Br, compounds, contribute supramolecular architectures leading 2D or 3D structures.