The synthesis, crystal structure and Hirshfeld surface analysis of the thio-phene derivatives 5-(phenyl-sulfon-yl)-5,6-di-hydro-benzo[4,5]thieno[3,2- j ]phenanthridine and ( E )- N -{2-[2-(benzo[ b ]thiophen-2-yl)ethenyl]phen-yl}- N -(prop-2-yn-1-yl)benzene-sulfonamide.

In both of the title compounds, C 26 H 19 NO 2 S 2 , ( I ), and C 25 H 19 NO 2 S 2 , ( II ), the benzo-thio-phene rings are essentially planar with maximum deviations of 0.026 (1) and -0.016 (1) Å for the carbon and sulfur atoms in compounds ( I ) and ( II ), respectively. In ( I ), the thio-phene ring system is almost orthogonal to the phenyl ring attached to the sulfonyl group, subtending a dihedral angle of 88.1 (1)°, and the di-hydro-pyridine ring adopts a screw-boat conformation. In both compounds, the mol-ecular structure is consolidated by weak C-H⋯O intra-molecular inter-actions formed by the sulfone oxygen atoms, which generate S (5) ring motifs. In the crystal of II , mol-ecules are linked via C-H⋯O hydrogen bonds, generating C (7) chains running along the [100] direction. No significant inter-molecular inter-actions are observed in I .