Find in Library

The title compound <i>N</i>-(2,4-difluorophenyl)-2-fluorobenzamide (<b>Fo24</b>) was synthesized in high yield (1.09 g; 87%) using standard synthetic procedures from the condensation reaction of 2-fluorobenzoyl chloride with 2,4-difluoroaniline. Crystals of <b>Fo24</b> were grown from CH₂Cl₂ at room temperature. The <b>Fo24</b> crystal structure was determined using single-crystal X-ray diffraction methods at 294 (1) K in space group <i>Pn</i> (No. 7). <b>Fo24</b> is the second regular tri-fluorinated benzamide with the formula C₁₃H₈F₃N₁O₁ to be reported and contrasts with the more common difluorinated and tetra-fluorinated analogues. In <b>Fo24</b>, both aromatic rings are effectively coplanar with an interplanar angle of 0.7(2)°. The central amide group plane is oriented by 23.04(18)° and 23.69(17)° from both aromatic rings, forming an intramolecular contact with an <i>ortho</i>-F12 atom with H1⋯F12 = 2.12(4) Å. The primary hydrogen bonds are 1D amide–amide interactions that form along the <i>b</i>-axis direction. In addition, weaker C-H⋯F/O interactions are noted: a <i>R</i>²₂(12) synthon involving two C-H, a N-H and two C-F groups, with C-F⋯C ring–ring stacking contacts completing the interactions.