<i>N</i>-(2,3-Difluorophenyl)-2-fluorobenzamide

oleh: Niall Hehir, John F. Gallagher

Format: Article
Diterbitkan: MDPI AG 2023-09-01

Deskripsi

The title compound <i>N</i>-(2,3-difluorophenyl)-2-fluorobenzamide or (<b>Fo23</b>) was obtained at high yield (88%) from the condensation reaction of 2-fluorobenzoyl chloride with 2,3-difluoroaniline using standard synthetic procedures. The crystal structure of <b>Fo23</b> was determined at 294 (1) K using single crystal X-ray diffraction methods and represents the first regular tri-fluorinated benzamide with formula C<sub>13</sub>H<sub>8</sub>F<sub>3</sub>NO compared to the difluorinated and tetra-fluorinated analogues. In the structure, both aromatic rings are effectively co-planar, with an interplanar angle of 0.5(2)°; however, the central amide group plane is oriented by 23.17(18)° and 23.44(17)° from the aromatic rings as influenced by 1D amide⋯amide hydrogen bonds along the <i>a</i>-axis direction. Longer C-H⋯F/O interactions and the arrangement of a <i>R</i><sup>2</sup><sub>2</sub>(12) synthon involving two C-F, a N-H and two C-H, together with C-F⋯C ring⋯ring stacking contacts, complete the interactions in the <b>Fo23</b> crystal structure.