Crystal structure of (Z)-1-(3,4-dichlorophenyl)-3-methyl-4-[(naphthalen-1-yl­amino)(p-tolyl)methylidene]-1H-pyrazol-5(4H)-one

The title Schiff base compound, C₂₈H₂₁Cl₂N₃O, was synthesized by the condensation of 1-(3,4-di­chloro­phen­yl)-3-methyl-4-(4-methyl­benzo­yl)-1H-pyrazol-5(4H)-one with 1-aminona­phthalene. The p-tolyl ring is normal to the pyrazole ring, with a dihedral angle of 88.02 (14)°, and inclined to the naphthalene ring system by 78.60 (12)°. The pyrazole ring is inclined to the naphthalene ring system and the di­chloro-substituted benzene ring by 63.30 (12) and 11.03 (13)°, respectively. The amino group and carbonyl oxygen atom are involved in an intra­molecular N—H...O hydrogen bond enclosing an S(6) ring motif. There is also a short C—H...O contact involving the carbonyl O atom and the adjacent benzene ring. In the crystal, mol­ecules are linked by C—H...π inter­actions, forming a three-dimensional structure.

Crystal structure of (4Z)-1-(3,4-di­chloro­phen­yl)-4-[hy­droxy(4-methyl­phen­yl)methyl­idene]-3-methyl-4,5-di­hydro-1H-pyrazol-5-one

The title compound, C₁₈H₁₄Cl₂N₂O₂, crystallizes with two mol­ecules, A and B, in the asymmetric unit. In mol­ecule A, the dihedral angles between the central pyrazole ring and pendant di­chloro­benzene and p-tolyl rings are 2.18 (16) and 46.78 (16)°, respectively. In mol­ecule B, the equivalent angles are 27.45 (16) and 40.45 (18)°, respectively. Each mol­ecule features an intra­molecular O—H...O hydrogen bond, which closes an S(6) ring and mol­ecule A also features a C—H...O inter­action. In the crystal, weak C—H...π interactions and aromatic π–π stacking [shortest centroid–centroid separation = 3.707 (2) Å] generate a three-dimensional network.