(2E)-2-[2-(4-Chlorophenyl)hydrazin-1-ylidene]-4,4,4-trifluoro-3-oxobutanal

Abstract

The title compound, C10H6ClF3N2O2, was synthesized by coupling 4-dimethylamino-1,1,1-trifluorobut-3-en-2-one with 4-chlorobenzenediazonium chloride. It crystallizes with two molecules in the asymmetric unit, which form two similar centrosymmetric dimers via hydrogen bonds. Extensive electron delocalization and intramolecular N—H...O hydrogen bonds are responsible for a planar conformation of the molecules (maximum deviations = 0.010 and −0.015 Å for the two molecules). In addition to hydrogen bonds, π–π stacking interactions with centroid–centroid distances of 3.604 (2) and 3.583 (2) Å contribute to the stability of the crystal structure.