In the title compound, C(17)H(14)ClFO(2)S, the 4-fluoro-phenyl ring is rotated slightly out of the benzofuran plane, as indicated by the dihedral angle of 8.32 (5)°. The crystal structure features a short Cl⋯O contact [3.092 (1) Å].

In the title compound, C(21)H(21)FO(2)S, the cyclo-hexyl ring adopts a classic chair conformation. The 4-fluoro-phenyl ring makes a dihedral angle of 31.05 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯O and C-H⋯π inter-actions.

In the title compound, C(21)H(21)FO(3)S, the cyclo-hexyl ring adopts a chair conformation. The 3-fluoro-phenyl ring makes a dihedral angle of 79.15 (4)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O hydrogen bonds and C-H⋯π inter-actions.

In the title compound, C(17)H(15)BrO(2)S, the 4-bromo-phenyl ring makes a dihedral angle of 87.12 (6)° with the mean plane of the benzofuran fragment. In the crystal, mol-ecules are linked by weak C-H⋯O and C-H⋯π inter-actions.

In the title compound, C(17)H(14)FIO(2)S, the 4-fluoro-phenyl ring makes a dihedral angle of 18.88 (9)° with the mean plane of the benzofuran ring. In the crystal, pairs of inter-molecular I⋯O contacts [3.153 (2) Å] link the mol-ecules into inversion dimers.

In the title compound, C(18)H(17)ClO(2)S, the 4-chloro-phenyl ring is oriented approximately perpendicular to the mean plane of the benzofuran ring [dihedral angle = 87.49 (5)°]. In the crystal, mol-ecules are linked through weak inter-molecular C-H⋯π inter-actions, forming left- and right-handed pseudo-helices along the a axis.