The synthesis, crystal structure and Hirshfeld surface analysis of the thiophene derivatives 5-(phenylsulfonyl)-5,6-dihydrobenzo[4,5]thieno[3,2-j]phenanthridine and (E)-N-{2-[2-(benzo[b]thiophen-2-yl)ethenyl]phenyl}-N-(prop-2-yn-1-yl)benzenesulfonamide

Abstract

In both of the title compounds, C26H19NO2S2, (I), and C25H19NO2S2, (II), the benzothiophene 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 thiophene ring system is almost orthogonal to the phenyl ring attached to the sulfonyl group, subtending a dihedral angle of 88.1 (1)°, and the dihydropyridine ring adopts a screw–boat conformation. In both compounds, the molecular structure is consolidated by weak C—H...O intramolecular interactions formed by the sulfone oxygen atoms, which generate S(5) ring motifs. In the crystal of II, molecules are linked via C—H...O hydrogen bonds, generating C(7) chains running along the [100] direction. No significant intermolecular interactions are observed in I.

Keywords

• crystal structure
• thiophene
• benzothiophene
• dihydrobenzene
• dihydropyridine 5-(phenylsulfonyl)
• 12-(phenylsulfonyl)
• phenanthridine hydrogen bonding
• hirshfeld surface analysis.