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In the title compound, C(19)H(18)N(4)O(3), the pyrazole ring is oriented at dihedral angles of 41.12 (7) and 12.25 (10)°, respectively, with respect to the planes of the phenyl and benzene rings. Intra-molecular N-H⋯O and O-H⋯O hydrogen bonds generate seven- and six-membered S(7) and S(6) ring motifs, respectively.

The title Schiff base compound, C20H14ClNO2, adopts an E configuration about the azomethine bond. The phenol and chlorobenzene rings form dihedral angles of 84.71 (9) and 80.70 (8)°, respectively, with the phenyl ring and are twisted by 15.32 (8)° with respect to one another. The molecular conformation is stabilized by an intramolecular O—H...N hydrogen bond, which forms an S(6) ring motif. In the crystal, molecules are linked by C—H...O hydrogen bonds, forming columns parallel to the a axis.

In the title compound, C15H12N2O2, the seven-membered ring bearing the three methylene C atoms displays a puckered conformation, with the methylene C atoms deviating from the plane of the benzene ring by 0.05 (1), 0.98 (1) and 1.04 (1) Å. The phenanthroline unit is not planar; the dihedral angles between this benzene ring and the other pyridyl rings are 9.62 (4) and 9.31 (4)°. The crystal packing is stabilized by π–π interactions between two phenanthroline ring systems, forming a centrosymmetric dimer with a centroid–centroid distance of 3.656 (1) Å.