Structures of 1-(substituted-phenyl)-4-hydroxymethyl- and -4-fluoromethyl-1,2,3-triazoles

Abstract

The crystal structures of 4-FCH₂-1-(4-X-phenyl)-triazole (1: X = Cl, Br and CN) and 4-HOCH₂-1-(4-X-phenyl)-triazole (2: X = Cl, Br and CN) are reported. Each of the pairs, (1: X = Cl) and (1: X = Br) and (2: X = Cl) and (2: X = Br), are isostructural. There are no strong intermolecular interactions in any of the compounds 1. Present in (1: X = CN), are C—H···N, C—H···F and C—H···π hydrogen bonds, and π···π stacking interactions, while in (2: X = Cl and Br) present are C—H···N, C—H···F and C—X···π, hydrogen bonds, with resulting different supramolecular arrays produced for the halo, on one hand, and cyano derivatives, on the other. The hydroxyl-triazole nitrogen interactions in 2 are the strongest intermolecular interactions present in 2. In the case of (2: X = Cl and Br), augmenting this strong O—H···N hydrogen bond with a weaker C—H···O hydrogen bond results in a [C(6)R²₂(10)] chain of molecules propagated head-to-tail along the b axis. In contrast, this strong O—H···N hydrogen bond in (2: X = CN), now augmented by C—H···N(cyano nitrogen), results in a chain of molecules, [C(19)R²₂(10)R²₂(10)]. Further weaker intermolecular interactions of the types, C—H···N and C—H···O hydrogen bonds and π···π stacking interactions for (2: X = CN), and of the types, C—H···O and C—X···π hydrogen bonds, and π···π stacking interactions for (2: X = Cl and Br) generate significantly different supramolecular arrays.