The syntheses, structures and spectroscopic properties of tricarbonylrhenium(I) complexes with N,N′-bis(2-bromo, 4-bromo, 4-chloro and 3-methoxybenzaldehyde)-1,2-diiminoethane Schiff base ligands have been investigated in this paper. Characterization of these complexes was carried out with FTIR, NMR, UV–Vis spectroscopy, elemental analysis and X-ray crystallography. The electrochemical behavior of the investigated complexes has been studied by cyclic voltammetry. The crystal structures of the 4-chloro, 4-bromo and 4-methoxy substituted complexes are stabilized by intermolecular C–H⋯Cl and C–H⋯O hydrogen bonds. The remarkable features of the 2-bromo, 4-bromo and 4-chloro substituted complexes are short intermolecular halogen–oxygen contacts. In the 4-bromo complex, short intermolecular Br⋯O and O⋯O contacts link neighboring molecules along the [1 0 0] direction, which are further stabilized by short intermolecular π⋯π interactions. In 2-bromo complex, intermolecular Br⋯O interactions link neighboring molecules into 1D extended chains along the [0 1 0] and [0 0 1] directions, forming a 2D network which is parallel to the bc-plane.