In title compound, C17H15ClO3, the dihedral angle between the benzene and chloro-phenyl rings is 18.46 (7)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen contacts, enclosing an R22(14) ring motif, and by a further C-H⋯O hydrogen contact, forming a two-dimensional supra-molecular structure extending along the direction parallel to the ac plane. Hirshfeld surface analysis shows that van der Waals inter-actions constitute the major contribution to the inter-molecular inter-actions, with H⋯H contacts accounting for 36.2% of the surface.
In the mol-ecule of the title compound, C17H14BrFO3, the aromatic rings are tilted with respect to the enone bridge by 13.63 (14) and 4.27 (15)°, and form a dihedral angle 17.91 (17)°. In the crystal, centrosymmetrically related mol-ecules are linked by pairs of C-H⋯O hydrogen bonds into dimeric units, forming rings of R22(14) graph-set motif. The dimers are further connected by weak C-H⋯O hydrogen inter-actions, forming layers parallel to (10). Hirshfeld surface analysis shows that van der Waals inter-actions constitute the major contribution to the inter-molecular inter-actions, with H⋯H contacts accounting for 29.7% of the surface.
In the cation of the title salt, C20H19N2O+·Br-, the phenyl rings are inclined to one another by 38.38 (8)°, whereas the central phenyl ring and the pyridiniminium ring are almost perpendicular with a dihedral angle of 87.37 (9)°. The N+=C cationic double bond was verified by the shortened bond length of 1.337 (2) Å. In the crystal, the Br- anion is linked to the cation by an N-H⋯Br hydrogen bond. C-H⋯O hydrogen bonds link adjacent pyridiniminium cations into inversion dimers with an R22(18) graph-set motif. These dimers are stacked in a phen-yl-phenyl T-shaped geometry through C-H⋯π inter-actions. A Hirshfeld surface analysis was conducted to verify the contributions of the different inter-molecular inter-actions.