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N-(2,4-Difluorophenyl)-2-fluorobenzamide

Gallagher, John F. orcid logoORCID: 0000-0003-4130-4556 and Hehir, Niall (2024) N-(2,4-Difluorophenyl)-2-fluorobenzamide. Molbank, 2024 (1). ISSN 1422-8599

Abstract
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
Subjects:Physical Sciences > Chemistry
DCU Faculties and Centres:DCU Faculties and Schools > Faculty of Science and Health > School of Chemical Sciences
Publisher:MDPI
Official URL:https://doi.org/10.3390/M1771
Copyright Information:© 2024 The Authors
Funders:Dublin City University, Meath VEC
ID Code:29631
Deposited On:23 Feb 2024 11:02 by John Gallagher . Last Modified 23 Feb 2024 11:02
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