Crystal structures of 1-benzenesulfonyl-2-methyl-3-(4-nitrobenzoyl)-2,3-dihydro-1H-indole and 1-benzenesulfonyl-2-methyl-3-[(thiophen-2-yl)carbonyl]-2,3-dihydro-1H-indole

Abstract

In the title indole derivatives, C22H16N2O5S, (I) and C20H15NO3S2, (II), the sulfonyl-bound phenyl rings are almost orthogonal to the indole ring system, subtending dihedral angles of 88.33 (10) and 87.58 (16)°, respectively. In both compounds, the sulfonyl S atom has a distorted tetrahedral geometry [O—S—O = 119.98 (9) and N—S—C = 104.01 (8)° for compound (I) and O—S—O = 120.08 (18) and N—S—C = 104.91 (14)° for compound (II)] and the sum of the bond angles at N indicatessp2hybridization. The molecules of both (I) and (II) feature intramolecular C—H...O hydrogen bonds that generateS(6) ring motifs with the sulfone O atom. In the crystals, molecules of (I) are linked by C—H—O hydrogen bonds, formingR44(18) ring motifs while molecules of (II) are linked by C—H—O and C—H—S hydrogen bonds, formingR22(12) ring motifs. Compound (II) was refined as an inversion twin.