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 indicates sp2 hybridization. The molecules of both (I) and (II) feature intramolecular C-H...O hydrogen bonds that generate S(6) ring motifs with the sulfone O atom. In the crystals, molecules of (I) are linked by C-H-O hydrogen bonds, forming R44(18) ring motifs while molecules of (II) are linked by C-H-O and C-H-S hydrogen bonds, forming R22(12) ring motifs. Compound (II) was refined as an inversion twin.