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The title compound, C19H14F3NO2, crystallizes in the keto–amine tautomeric form, with a strong intra­molecular N—H...O hydrogen bond. The mol­ecule is almost planar; the dihedral angle between the naphthalene ring system and the benzene ring is 4.60 (7)°. In the crystal, mol­ecules are linked into chains along the c axis by C—H...O hydrogen bonds. The F atoms of the trifluoro­methyl group are disordered over two positions with refined site occupancies of 0.668 (9) and 0.332 (9).

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In the title compound, C18H15N5O2S, a weak intra­molecular C—H...S hydrogen bond results in a small dihedral angle of 3.71 (9)° between the methyl­phenyl and triazole rings, which, in turn, form dihedral angles of 80.09 (8) and 77.32 (8)°, respectively, with the benzoxazolone mean plane. In the crystal, N—H...O hydrogen bonds link mol­ecules into chains along [001], and weak C—H...N hydrogen bonds and π–π inter­actions between the five- and six-membered rings [centroid–centroid distances = 3.5074 (11) and 3.616 (1) Å] consolidate the crystal packing.
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