Exploring the simultaneous σ-hole/π-hole bonding characteristics of a Br⋯π interaction in an ebselen derivative experimental and theoretical electron-density analysis.

In this study, the nature and characteristics of a short Br⋯π interaction observed in an ebselen derivative, 2-(2-bromophenyl)benzo[][1,2]selenazol-3(2)-one, has been explored. The electronic nature of this Br⋯π interaction was investigated high-resolution X-ray diffraction and periodic density functional theory calculations using atoms-in-molecules (AIM) analysis. This study unravels the simultaneous presence of σ-hole and π-hole bonding characteristics in the same interaction. The dual characteristics of this unique Br⋯π interaction are further established molecular electrostatic potentials (MESPs) and natural bond orbitals (NBOs).