Structural and spectral studies of N-2-(pyridyl)-, N-2-(4-, 5-, and 6-picolyl)- and N-2-(4,6-lutidyl)-N '-2-methoxyphenylthioureas

N-2-(pyridyl)-N ' -2-methoxyphenylthiourea PyTu2OMe, monoclinic, C2/c, a=15 .727(3), b=11.251(2), c=15.026(4) Angstrom, beta = 104.78(2)degrees, V = 25 70.9(2) Angstrom (3) and 2 = 8; N-2-(4-picolyl)-N ' -2-methoxyphenylthioure a, 4PicTu2OMe, orthothombic, Pbca, a = 11.439(9), b = 15.897(6), c = 14.920 (6) Angstrom, V = 2713.0(4) Angstrom (3) and Z = 8; N-2-(5-picolyl)-N ' -2- methoxyphenylthiourea, 5PicTu2OMe. triclinic, P-1, a = 7.586(2), b = 8.505( 3), c = 11.308(5) Angstrom, alpha = 73.29(3), beta = 89.04(3), gamma = 83.3 8(3)degrees, V = 694.0(6)Angstrom (3) and Z = 2; N-2-(6-picolyl)-N ' -2-met hoxyphenylthiourea 6PicTu2OMe, monoclinic, P2(1)/c, a = 11.372(4), b = 15.8 08(4), c = 16.141(7) Angstrom, beta = 102.96(3)degrees V = 2827.8(3) Angstr om (3) and Z = 8 and N-2-(4,6-lutidyl)-N ' -2-methoxyphenylthiourea, 3,6LuT u2OMe, monoclinic, P2(1)/n, a = 7.546(4), b = 23.400(5), c = 8.927(5) Angst rom, beta = 109.42(5)degrees V = 1486.7(2) Angstrom (3) and Z = 4. Some of these molecules have a bifurcated intramolecular hydrogen bond between N 'H and the pyridyl nitrogen and the 2-methoxy oxygen, and all have intermolec ular hydrogen bonding between NH and a thione sulfur of a second molecule t o form centrosymmetric dimers. Solution H-1 NMR studies (CDCl3) show the N 'H resonance considerably downfield for each thiourea and its position, as well as that of NH, is affected by substituents on the pyridyl ring. (C) 20 01 Elsevier Science B.V. All rights reserved.