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.

Keywords

• crystal structure
• indole
• nitrophenyl
• thiophen:(phenyl)methanone
• inter- molecular and intra molecular hydrogen bonds