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Hehir, Niall and Gallagher, John F. orcid logoORCID: 0000-0003-4130-4556 (2023) N-(2,3-Difluorophenyl)-2-fluorobenzamide. Molbank, 2023 (9). ISSN 1422-8599

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.
Item Type:Article (Published)
Additional Information:CCDC 2284761 contains the supplementary crystallographic data for this paper. All other data in this paper are in the supplementary information section.
Uncontrolled Keywords:Fluorine; Benzamides; Amide; crystal structure; conformational analysis; fluorine; hydrogen bonding; molecular stacking
Subjects:Physical Sciences > Chemistry
Physical Sciences > Organic chemistry
Physical Sciences > Crystallography
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Official URL:https://doi.org/10.3390/M1717
Copyright Information:© 2023 The Authors
Funders:Dublin City University, Meath VEC
ID Code:29042
Deposited On:15 Sep 2023 15:07 by John Gallagher . Last Modified 15 Sep 2023 15:07

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