The crystal structures determination and Hirshfeld surface analysis of N-(4-bromo-3-meth-oxy-phen-yl)- and N-{[3-bromo-1-(phenyl-sulfon-yl)-1H-indol-2-yl]meth-yl}- derivatives of N-{[3-bromo-1-(phenylsulfon-yl)-1H-indol-2-yl]meth-yl}benzene-sulfonamide.

Two new phenyl-sulfonyl-indole derivatives, namely, N-{[3-bromo-1-(phenyl-sulfon-yl)-1H-indol-2-yl]meth-yl}-N-(4-bromo-3-meth-oxy-phen-yl)benzene-sulfonamide, C28H22Br2N2O5S2, (I), and N,N-bis-{[3-bromo-1-(phenyl-sulfon-yl)-1H-indol-2-yl]meth-yl}benzene-sulfonamide, C36H27Br2N3O6S3, (II), reveal the impact of intra-molecular π-π inter-actions of the indole moieties as a factor not only governing the conformation of N,N-bis-(1H-indol-2-yl)meth-yl)amines, but also significantly influencing the crystal patterns. For I, the crystal packing is dominated by C-H⋯π and π-π bonding, with a particular significance of mutual indole-indole inter-actions. In the case of II, the mol-ecules adopt short intra-molecular π-π inter-actions between two nearly parallel indole ring systems [with the centroids of their pyrrole rings separated by 3.267 (2) Å] accompanied by a set of forced Br⋯O contacts. This provides suppression of similar inter-actions between the mol-ecules, while the importance of weak C-H⋯O hydrogen bonding to the packing naturally increases. Short contacts of the latter type [C⋯O = 3.389 (6) Å] assemble pairs of mol-ecules into centrosymmetric dimers with a cyclic R 2 2(13) ring motif. These findings are consistent with the results of a Hirshfeld surface analysis and together they suggest a tool for modulating the supra-molecular behavior of phenyl-sulfonyl-ated indoles.