In the title mol­ecule, C23H18FN3O2, the mean plane of the indole system forms dihedral angles of 44.23 (8) and 14.54 (7)°, respectively, with the phenyl and benzene rings. In the crystal, inter­molecular N—H⋯O hydrogen bonds link mol­ecules into two-layer ribbons extended along the b axis. The crystal packing also exhibits weak inter­molecular C—H⋯O, C—H⋯F and C—H⋯π inter­actions.

In the title compound, C21H17FN4O2S, the planar indole fused-ring [maximum deviation 0.009 (1) Å] makes dihedral angles of 54.75 (9) and 14.90 (9)°, respectively, with the phenyl ring and the dihydro­thia­zolyl ring. The –CH2CH=CH2 substituent is disordered over two positions in a 0.51 (1):0.49 (1) ratio. An intra­molecular N—H⋯S hydrogen bond generates an S(5) ring motif. The two independent mol­ecules are linked into a dimer by two N—H⋯O hydrogen bonds, forming an R 2 2(10) ring motif. The crystal structure features inter­molecular C—H⋯π and π–π stacking [centroid–centroid distance = 3.679 (1) Å] inter­actions. C—H⋯O and C—H⋯F inter­actions are also present.

In the title compound, C15H14N4O3S2, the hydr­oxy group is disordered over two positions with occupancies of 0.619 (5) and 0.381 (5). The benzene ring attached to the heterocycle makes a dihedral angle of 86.92 (9)° with respect to the best plane through the five-membered ring. The crystal packing is stabilized by inter­molecular O—H⋯O, N—H⋯S, N—H⋯N, C—H⋯O and C—H⋯N hydrogen bonds, and N—H⋯π and C—H⋯π inter­actions.