Crystal structure determination and Hirshfeld surface analysis of -acetyl--3-meth-oxy-phenyl and -(2,5-di-meth-oxy-phen-yl)--phenyl-sulfonyl derivatives of -[1-(phenyl-sulfon-yl)-1-indol-2-yl]methanamine.

Two new [1-(phenyl-sulfon-yl)-1-indol-2-yl]methanamine derivatives, namely, -(3-meth-oxy-phen-yl)--{[1-(phenyl-sulfon-yl)-1-indol-2-yl]meth-yl}acetamide, CHNOS, (), and -(2,5-di-meth-oxy-phen-yl)--{[1-(phenyl-sulfon-yl)-1-indol-2-yl]meth-yl}benzene-sulfonamide, CHNOS, (), reveal a nearly orthogonal orientation of their indole ring systems and sulfonyl-bound phenyl rings. The sulfonyl moieties adopt the anti-periplanar conformation. For both compounds, the crystal packing is dominated by C-H⋯O bonding [C⋯O = 3.312 (4)-3.788 (8) Å], with the structure of exhibiting a larger number, but weaker bonds of this type. Slipped π-π inter-actions of anti-parallel indole systems are specific for , whereas the structure of delivers two kinds of C-H⋯π inter-actions at both axial sides of the indole moiety. These findings agree with the results of Hirshfeld surface analysis. The primary contributions to the surface areas are associated with the contacts involving H atoms. Although manifests a larger fraction of the O⋯H/H⋯O contacts (25.8 22.4%), most of them are relatively distal and agree with the corresponding van der Waals separations.