Crystal structure determination and Hirshfeld surface analysis of N-acetyl-N-3-methoxyphenyl and N-(2,5-dimethoxyphenyl)-N-phenylsulfonyl derivatives of N-[1-(phenylsulfonyl)-1H-indol-2-yl]methanamine

Abstract

Two new [1-(phenylsulfonyl)-1H-indol-2-yl]methanamine derivatives, namely, N-(3-methoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}acetamide, C24H22N2O4S, (I), and N-(2,5-dimethoxyphenyl)-N-{[1-(phenylsulfonyl)-1H-indol-2-yl]methyl}benzenesulfonamide, C29H26N2O6S2, (II), 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 II exhibiting a larger number, but weaker bonds of this type. Slipped π–π interactions of antiparallel indole systems are specific for I, whereas the structure of II delivers two kinds of C—H...π interactions 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 II manifests a larger fraction of the O...H/H...O contacts (25.8 versus 22.4%), most of them are relatively distal and agree with the corresponding van der Waals separations.

Keywords

• crystal structure
• 1h-indole
• acetamide
• phenylsulfonamide
• hydrogen bonding
• hirshfeld surface analysis