Preparation and crystal structure of the potentially tridentate substituted phenoxyacetic acid (2-Benzoyl-5-Methoxyphenoxy)acetic acid and its complex adduct with sodium

The ring-substituted phenoxyacetic acid (2-benzoyl-5-methoxyphenoxy)acetic acid (HL) (3) and its complex adduct dimer (4) with sodium, [Na(L)(HL)].2HL, have been synthesized and their structures determined by X-ray diffraction. The acid (3) does not have the usual cyclic hydrogen-bonded dimer association, but instead has three-centre intramolecular hydrogen bonding between the carboxyl proton and both the ether and keto oxygens [O---O, 2.602(3), 2.711(3) Å respectively]. Each sodium in the centrosymmetric complex dimer (4) is seven-coordinate [Na-O, 2.313(5)-2.612(5) Å], involving the ‘inner’ three oxygens of both a protonated and an ionic ligand molecule. In addition, one of these carboxyl oxygens forms a bridge to the inversion-related sodium, while the uncoordinated carboxyl oxygen is hydrogen-bonded to a protonated carboxy group [O---O, 2.464(8) Å]. The molecules of the lattice acid have only one hydrogen-bonded association with the second uncoordinated carboxy group in the dimer [O---O, 2.513(7) Å]