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The characteristics (equilibrium geometries, interaction energies, charge transfer and orbital interactions) of the intermolecular interactions in complexes thiophene–XY(X, Y=F, Cl, Br) are examined at the second-order Møller–Plesset (MP2) level. For each complex, three types of intermolecular interactions (π-halogen bonded, σ-halogen bonded and hydrogen bonded) are observed and the π-halogen bonded...