Structural and spectral studies of 3-(2-hydroxyphenylimino)-1-phenylbutan-1-one and its diorganotin(IV) complexes

Abstract

Abstract Two diorganotin(IV) complexes of the general formula R2Sn[Ph(O)C CH-C(Me) N–C6H4(O)] (R = Ph, 1a; R = Me, 1b) have been synthesized from the corresponding diorganotin(IV) dichlorides and the ligand, 3-(2-hydroxyphenylimino)-1-phenylbutan-1-one (1) in methanol at room temperature in presence of triethylamine. Both compounds have been characterized by elemental analyses, IR and 1H, 13C, 15N, 119Sn NMR spectra. The structures of the free ligand and the complexes have been confirmed by single crystal X-ray diffraction. There are three independent molecules in the crystal structure of the ligand 1 and in all three the O-bound proton is transferred to the imine nitrogen and makes an intramolecular N–H⋯O hydrogen bond with the carbonyl oxygen. In turn this makes an intermolecular hydrogen bond with the phenolic H atom. The crystal structure of 1 is trigonal and a new polymorph; triclinic and monoclinic forms have already been published. In 1a, the central tin atom adopts distorted trigonal–bipyramidal coordination geometry whereas in dimeric 1b it is distorted octahedral when including the intermolecular Sn–O(phenolic) bond [2.7998(20) A]. The δ (119Sn) values for the complexes 1a and 1b are −306.6 and −127.9 ppm, respectively, thus indicating penta-coordinated Sn centres in solution.