The crystal structure of carbamoyl fluoride, NH2COF

Although first synthesized in 1940, the X-ray crystal structure of carbamoyl fluoride, NH 2 COF, has until now remained unknown. [ 1 ] NH 2 COF crystallizes in the orthorhombic space group Ibam , is planar, and exhibits a short C-N bond length, 1.3168(13) Å, implying a significant degree of donation from the nitrogen lone pair. The structure features one molecule in the asymmetric unit and eight molecules in the unit cell. There are four molecules in two planar layers that are connected by a network of NH·O hydrogen bonds with N·O distances of 2.987(2) Å and 2.945(2) Å. The compound was also studied by quantum chemical calculations at both the ab initio (MP2) and density functional theory (B3LYP) level.