The crystal structures determination and Hirshfeld surface analysis of <i>N</i>-(4-bromo-3-methoxyphenyl)- and <i>N</i>-{[3-bromo-1-(phenylsulfonyl)-1<i>H</i>-indol-2-yl]methyl}- derivatives of <i>N</i>-{[3-bromo-1-(phenylsulfonyl)-1<i>H</i>-indol-2-

Two new phenyl-sulfonyl-indole derivatives, namely, <i>N</i>-{[3-bromo-1-(phenyl-sulfon-yl)-1<i>H</i>-indol-2-yl]meth-yl}-<i>N</i>-(4-bromo-3-meth-oxy-phen-yl)benzene-sulfonamide, C₂₈H₂₂Br₂N₂O₅S₂, (<b>I</b>), and <i>N</i>,<i>N</i>-bis-{[3-bromo-1-(phenyl-sulfon-yl)-1<i>H</i>-indol-2-yl]meth-yl}benzene-sulfonamide, C₃₆H₂₇Br₂N₃O₆S₃, (<b>II</b>), reveal the impact of intra-molecular π-π inter-actions of the indole moieties as a factor not only governing the conformation of <i>N</i>,<i>N</i>-bis-(1<i>H</i>-indol-2-yl)meth-yl)amines, but also significantly influencing the crystal patterns. For <b>I</b>, 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 <b>II</b>, 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 <i>R</i> 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.