The title compound N-(2,4-difluorophenyl)-2-fluorobenzamide (Fo24) 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 Fo24 were grown from CH2Cl2 at
room temperature. The Fo24 crystal structure was determined using single-crystal X-ray diffraction
methods at 294 (1) K in space group Pn (No. 7). Fo24 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 Fo24, 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 ortho-F12 atom with H1· · · F12 = 2.12(4) Å.
The primary hydrogen bonds are 1D amide–amide interactions that form along the b-axis direction.
In addition, weaker C-H· · · F/O interactions are noted: a R2 2
(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.
Metadata
Item Type:
Article (Published)
Refereed:
Yes
Uncontrolled Keywords:
amide; crystal structure; fluorine; hydrogen bonding; molecular stacking; ring stacking