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In the title mol­ecule, C20H17F2NO, which adopts an E conformation with respect to the imine C=N double bond, the mean planes of the naphthalene ring system and the difluoro­phenyl ring form a dihedral angle of 85.82 (7)°. An intra­molecular C—H...N hydrogen bond occurs. In the crystal, weak C—H...F hydrogen bonds link the mol­ecules into zigzag chains along [010].

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The title Schiff base, C23H27ClN2O adopts the phenol–imine tautomeric form, with an intra­molecular O—H...N hydrogen bond, which generates an S(6) ring motif. Three C atoms of the heterocyclic moiety of the hexa­hydro­pyrido­quinoline unit, as well as the two methyl groups bonded to one of these C atoms, are disordered over two set of sites, with anoccupancy ratio of 0.740 (4):0.260 (4).
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