Crystal-structure determination and Hirshfeld surface analysis of two new thiophene derivatives: (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}benzenesulfonamide and (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]-5-fluorophenyl}-N-(but-2-yn-1-yl)benzenesulfonamide

Abstract

In the title compounds, C22H16FNO2S2 (I) and C26H20FNO2S2 (II), the benzothiophene rings are essentially planar with maximum deviations of 0.009 (1) and 0.001 (1) Å for the carbon and sulfur atom in compounds I and II, respectively. In I, the thiophene ring system is almost orthogonal to the phenyl ring attached to the sulfonyl group, with a dihedral angle of 77.7 (1)°. In compound I, the molecular structure is stabilized by weak C—H...O intramolecular interactions formed by the sulfone oxygen atoms, which generate two S(5) ring motifs. In the crystal of I, N—H...O hydrogen bonds link the molecules into R22(8) rings, which are connected into a C(10) chain via C—H...F hydrogen bonds. Intermolecular C—H...π interactions are also observed. In compound II, the molecules are linked via C—H...O and C—H...F hydrogen bonding, generating infinite C(11) and C(13) chains running parallel to [010].

Keywords

• crystal structure
• thiophene
• benzothiophene
• flurophenyl
• phenylsulfonamide hydrogen bonding
• hirshfeld surface analysis