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

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].

Source: Acta Crystallographica Section E - July 21, 2023 Category: Chemistry Authors: Madhan, S. NizamMohideen, M. Pavunkumar, V. MohanaKrishnan, A.K. Tags: crystal structure thiophene benzothiophene flurophenyl phenylsulfonamide hydrogen bonding Hirshfeld surface analysis research communications Source Type: research