Synthesis, spectroscopic investigations and crystal structures of organotin(IV) derivatives of 2-amino-1-cyclopentene-1-carbodithioic acid

The organotin(IV) chlorides RnSnCl4−n (n=2, R=nBu or Ph; and n=3, R=Ph) react with 2-amino-1-cyclopentene-1-carbodithioic acid (ACDA) to give [Ph2SnCl(ACDA)] (1), [Ph2Sn(ACDA)2] (2), [Ph3Sn(ACDA)] (3) and [Bu2Sn(ACDA)2] (4). The new complexes have been characterized by elemental analysis, UV–Vis, IR,1H NMR, 119Sn NMR spectroscopy and mass spectrometry. On the basis of 119Sn NMR data the effective coordination number in solution is five. The structures of 1, 3 and 4 have been confirmed by X-ray crystallography. Crystals of 1 are monoclinic with space group P21/n. The tin environment is distorted trigonal bipyramid with Cl and sulfur atoms in apical positions. Crystals of 3 are orthorombic, P212121, and the structure is distorted trigonal bipyramid with one sulfur and phenyl in the axial position. Complex 4 crystallizes in the triclinic space group, P1̄, and the Sn atom shows extremely irregular octahedral coordination with four S atoms laying in the equatorial plane. In all complexes ACDA coordinates as an anisobidentate ligand and its orientation lends to form a NH⋯S intramolecular hydrogen bond. The packing is also stabilized by intermolecular hydrogen bonding.