A STRUCTURAL COMPARISON OF SOME AMINE-SUBSTITUTED AND THIONE-SUBSTITUTED TRIAZOLES

A series of amine- and thione-substituted triazoles have been synthesi zed and their structures determined by single-crystal X-ray diffractio n methods. The compounds differ in the identity of the amine- and alky l-substituents on the triazole ring. Crystal data for o-3-methyl-4,5-d ihydro-1H-1,2,4-triazole-5-thione, C8H8N4OS: triclinic, space group P (1) over bar, Z = 2, a = 10.490(2) Angstrom, b = 10.700(2) Angstrom, c = 4.2185(8) Angstrom, alpha = 92.68(2)degrees, beta = 90.17(2)degrees , gamma = 92.61(1)degrees, V = 472.5(1) Angstrom(3), R(F) = 0.040 for 151 variables and 1056 observations (I > 3 sigma(I)); no-3-ethyl-4,5-d ihydro-1H-1,2,4-triazole-5-thione, C9H10N4OS: triclinic, space group P (1) over bar Z = 2, a = 8.366(3) Angstrom, b = 9.296(2) Angstrom, c = 7.953(2) Angstrom, alpha = 113.72(2)degrees, beta = 108.54(3)degrees, gamma = 84.94(3)degrees, V = 536.3(3) Angstrom(3), R(F) = 0.037 for 1 36 variables and 1126 observations (I > 3 sigma(I)); o-3-propyl-4,5-di hydro-1H-1,2,4-triazole-5-thione, C10H12N4OS: triclinic, space group P (1) over bar, Z = 2, a = 9.149(3) Angstrom, b = 9.177(2) Angstrom, c = 8.045(4) Angstrom, alpha = 110.11(2)degrees, beta = 114.52(3)degrees , gamma = 86.44(2)degrees, V = 574.5(4) Angstrom(3), R(F) = 0.040 for 145 variables and 1414 observations (I > 3 sigma(I)); o)-3-ethyl-4,5-d ihydro-1H-1,2,4-triazole-5-thione, C11H13N5S: triclinic, space group P (1) over bar, Z = 2, a = 7.736(3) Angstrom, b = 11.752(4) Angstrom, c = 7.219(2) Angstrom, alpha = 93.68(3)degrees, beta = 106.26(3) Angstr om, gamma = 91.04(3)degrees, V = 628.3(4) Angstrom(3), R(F) = 0.043 fo r 154 variables and 1224 observations (I > 3 sigma(I)). The molecules show substantial variations in conformation as well as in crystal pack ing. The differences in molecular structure are discussed in terms of the potential of the molecules to act as bidentate ligands towards met al ions. (C) 1998 Elsevier Science B.V. All rights reserved.