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

Abstract

The crystal structures of two 1H-indole derivatives are described and the analysis of the inter­molecular contacts in the crystals using Hirshfeld surface analysis and two-dimensional fingerprint plots is reported.

Two new phenyl­sulfonyl­indole derivatives, namely, N-{[3-bromo-1-(phenyl­sulfon­yl)-1H-indol-2-yl]meth­yl}-N-(4-bromo-3-meth­oxy­phen­yl)benzene­sulfonamide, C₂₈H₂₂Br₂N₂O₅S₂, (I), and N,N-bis­{[3-bromo-1-(phenyl­sulfon­yl)-1H-indol-2-yl]meth­yl}benzene­sulfonamide, C₃₆H₂₇Br₂N₃O₆S₃, (II), reveal the impact of intra­molecular π–π inter­actions of the indole moieties as a factor not only governing the conformation of N,N-bis­(1H-indol-2-yl)meth­yl)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 inter­actions. In the case of II, the mol­ecules adopt short intra­molecular π–π inter­actions 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 inter­actions between the mol­ecules, 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 mol­ecules into centrosymmetric dimers with a cyclic R₂²(13) ring motif. These findings are consistent with the results of a Hirshfeld surface analysis and together they suggest a tool for modulating the supra­molecular behavior of phenyl­sulfonyl­ated indoles.