Organotin thiosemicarbazates. Crystal structure of triphenyltin 1-amino-4-(2-hydroxyphenyl)-2,3-diazapenta-(E)-1,(E)-3-dienyl-1-thiolate

Article abstract of DOI:10.1016/0022-328X(89)80082-8

Triphenyltin 1-amino-4-(2-hydroxyphenyl)-2,3-diazapenta-(E)-1,(E)-3-dienyl-1-thiolate, <(C6H5)3Sn-SC(N¹H2=N²-N³=C(CH3)(C6H4-2-OH)>, crystallizes in the triclinic space group P/1 with a 13.368(4), b 10.494(7), c 9.370(2) Angstroem, α 96.16(4) β 96.57(2), γ101.80(4) deg; Z=2.The crystal structure was determined from 3745 I>3?(I) Mo-K_α reflections and refined to R=0.034.The tin atom is in a distorted tetrahedral environment in which N² atom of the ligand is positioned at one face of the polyhedron at a distance of 2.872(4) Angstroem from the metal atom.The Sn-S distance is 2.440(2) Angstroem, and the S-C, C-N₂, N²-N³, N³-C bond lengths are 1.741(4), 1.289(6), 1.412(5) and 1.283(6) Angstroem, respectively.The otherwise planar thiosemicarbazate group is twisted (C-N²-N³-C torsional angle 43.9(5) deg) in an apparent attempt to bring its N³ atom in a position to chelate.The free hemihydrated thiosemicarbazone acid (monoclinic, C2/c, a 14.385(2), b 14.733(2), c 10.855(3) Angstroem, β 114.84(1) deg; Z=8 and R=0.036 for 1464 observed reflections) 1H2C(=S)N²H-N³=C(CH3)(C6H4-2-OH)>*0.5H2O, is a flat molecule (S-C 1.690(3), C-N² 1.345(3), N²-N³ 1.382(3), N³-C 1.290(3) Angstroem; C-N²-N³-C torsional angle 5.4(3) deg).The phenolic proton in the thiosemicarbazate and in the uncomplexed thiosemicarbazone is hydrogen-bonded to the N³ atom.