Structure and absolute configuration of (+)-6-[(4-chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole (vorozole) and its hydrobromide monohydrate

Abstract

The (+)-6-[(4-chlorophenyl)(1H-1,2,4-triazol-1-yl)methyl]-1-methyl-1H-benzotriazole base (1) and its hydrobromide salt (II) show similar bond angles except for the C-N-C angle of the 1,2,4-triazolyl moiety, which is smaller in (I) than in (II) because of the presence of the lone-pair electrons on the N atom of (I). The molecular conformation of both structures is different, the dihedral angles between the planar moieties are 105.3 (2), 84.6 (1) and 81.3 (1) o in (I) and 110.4 (2), 79.2 (2) and 108.8 (2) o in (II). The absolute configuration at the central chiral C atom of both molecules is S