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The title compound, C14H12FN3O, adopts an E conformation with respect to the azomethine double bond whereas the N and methyl C atoms are in a Z conformation with respect to the same bond. The ketonic O and azomethine N atoms are cis to each other. The non-planar mol­ecule [the dihedral angle between the benzene rings is 7.44 (11)°] exists in an amido form with a C=O bond length of 1.221 (2) Å. In the crystal, a bifurcated N—H...(O,N) hydrogen bond is formed between the amide H atom and the keto O and imine N atoms of an adjacent mol­ecule, leading to the formation of chains propagating along the b-axis direction. Through a 180° rotation of the fluoro­phenyl ring, the F atom is disordered over two sites with an occupancy ratio of 0.632 (4):0.368 (4).

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The title compound, C14H12FN3O, adopts an E conformation with respect to the azomethine bond. The pyridyl and fluoro­benzene rings make dihedral angles of 38.58 (6) and 41.61 (5)° respectively with the central C(=O)N2CC unit, resulting in a non-planar mol­ecule. The inter­molecular inter­actions comprise two classical N—H...O and N—H...N hydrogen bonds and four non-classical C—H...O and C—H...F hydrogen bonds. These inter­actions are augmented by a weak π–π inter­action between the benzene and pyridyl rings of neighbouring mol­ecules, with a centroid–centroid distance of 3.9226 (10) Å. This leads to a three-dimensional supra­molecular assembly in the crystal system. The F atom is disordered over two sites in a 0.559 (3): 0.441 (3) ratio, through a 180° rotation of the fluoro­benzene ring.
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