A new structurally characterized organotin/Schiff-base complex with approximately rectangular molecular boxes formed through hydrogen bonds

A new organotin/Schiff-base compound, C24H25Cl4NO3Sn .0.5C(6)H(6) (1), was prepared by the reaction of beta -n-butoxycarbonylethyltin trichlorides (2) with 3-hydroxy-1-naphthalideneaniline-4-Cl (3) in benzene, and characterized by single-crystal X-ray diffraction, TR, H-1 NMR, and elemental analysis. Yellow rectangular rods of the title compound crystallize as a benzene solvate of formula C24H25Cl4NO3Sn .0.5C(6)H(6) (1) in the triclinic space group P-l. The unit cell has dimensions a = 9.3624 (2) Angstrom, b = 12.4947(3) Angstrom, c = 13.4821(3) Angstrom, alpha = 70.7660(10)degrees, beta = 87.1870(10)degrees, gamma = 75.1270(10)degrees, V = 1438.13(6) Angstrom (3), and Z = 2. The structure was solved by direct method primarily and difmap secondarily. It is found that the OH hydrogen in free 2-hydroxy-1-naphthalideneaniline tautomerizes to the imine nitrogen due to the coordination of the phenolic oxygen atom with the Sn atom after the complex formation, while an intramolecular hydrogen bond still exists between O and N (N . . .O = 2.585(4) Angstrom). The Sn atl,ln is coordinated with three chloride atoms, one carbon atom and two oxygen atoms, resulting in a distorted octahedra. Thr most notable feature, of 1 lies in the pi-pi interaction among the approximately planer 2-oxygen-1-naphthalideneaniline moieties and the rectangular molecular boxes formed through hydrogen bonds in which the benzene molecules reside, (C) 2000 Elsevier Science B.V. All rights reserved.