The title compound, C22H22N2O4S2, was synthesized by the reaction of 1,4,5,8-naphthalene-tetra-carb-oxy-lic dianhydride with 3-(methyl-sulfan-yl)propyl-amine. The whole mol-ecule is generated by an inversion operation of the asymmetric unit. This mol-ecule has an anti form with the terminal methyl-thio-propyl groups above and below the aromatic di-imide plane, where four intra-molecular C-H⋯O and C-H⋯S hydrogen bonds are present and the O⋯H⋯S angle is 100.8°. DFT calculations revealed slight differences between the solid state and gas phase structures. In the crystal, C-H⋯O and C-H⋯S hydrogen bonds link the mol-ecules into chains along the [2 direction. adjacent chains are inter-connected by π-π inter-actions, forming a two-dimensional network parallel to the (001) plane. Each two-dimensional layer is further packed in an ABAB sequence along the c-axis direction. Hirshfeld surface analysis shows that van der Waals inter-actions make important contributions to the inter-molecular contacts. The most important contacts found in the Hirshfeld surface analysis are H⋯H (44.2%), H⋯O/O⋯H (18.2%), H⋯C/C⋯H (14.4%), and H⋯S/S⋯H (10.2%).
Keywords: DFT calculations; Hirshfeld surface analysis.; crystal packing; crystal structure; hydrogen bonding; naphthalenetetracarboxylic diimide.