The title compound N-(2,3-difluorophenyl)-2-fluorobenzamide or (Fo23) 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 Fo23 was determined at 294 (1) K using single crystal X-ray diffraction methods and represents the first regular tri-fluorinated benzamide with formula C13H8F3NO 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 a-axis direction. Longer C-H· · · F/O interactions and the arrangement of a R22(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 Fo23 crystal structure.
Metadata
Item Type:
Article (Published)
Refereed:
Yes
Additional Information:
CCDC 2284761 contains the supplementary crystallographic data for
this paper. All other data in this paper are in the supplementary information section.