Crystal structure, hydrogen bonds and C-X…p (X=H,F) interactions of a new acetyl phosphorylamidate

Abstract

Acetyl phosphorylamidates, with the general formula R\\\\\\'C(O)NHP(O)R2 have been attracted attention due to containing nitrogen-carbonyl and nitrogen-phosphoryl moieties, and special properties resulting from them such as acting as O,O-donor ligands and inhibitory of urease and acetylcholinesterase enzymes.<br><br>The new compound N-(4-fluorobenzoyl)-N\\\\\\\\\\\\\\',N\\\\\\\\\\\\\\'-bis (4-methyl-phenyl) phosphoric triamide was synthesized and characterized by 1H, 13C, 31P{1H}-NMR and IR spectroscopies and single crystal X-ray determination. The phosphorus atom has a distorted tetrahedral configuration and the phosphoryl and carbonyl groups are anti to each other. Important HBs of this compound is respectively involve the oxygen atoms of P=O and C=O in hydrogen bonding interaction with the H-NC(O)NHP(O) and H-Namide units. Another interesting feature of this structure is the existence of C-X…π (X = H, F) interactions [C(17)-H(17A)…C(20) & C(7)-H(7A)…C(19) and C(5)-F(1)…C(8)]. These non-covalent interactions and additional C(20)-H(20A)…F(1) are extended hydrogen-bonded chains in a 2-D array