Trimethyl[3-methyl-1-(o-tolenesulfonyl)indol-2-ylmethyl]ammonium iodide and benzyl[3-bromo-1-(phenylsulfonyl)indol-2-ylmethyl]tolylamine.

Abstract

The title compounds, C(20)H(25)N(2)O(2)S(+).I(-), (I), and C(29)H(25)BrN(2)O(2)S, (II), respectively, both crystallize in space group P-1. The pyrrole ring subtends an angle with the sulfonyl group of 33.6 degrees in (I) and 21.5 degrees in (II). The phenyl ring of the sulfonyl substituent makes a dihedral angle with the best plane of the indole moiety of 81.6 degrees in (I) and 67.2 degrees in (II). The lengthening or shortening of the C-N bond distances in both compounds is due to the electron-withdrawing character of the phenylsulfonyl group. The S atoms are in distorted tetrahedral configurations. The molecular structures are stabilized by C-H.O and C-H.I interactions in (I), and by C-H.O and C-H.N interactions in (II).