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The crystal structures of 4-FCH 2 -1-(4-X-phenyl)-triazole ( 1 : X = Cl, Br and CN) and 4-HOCH 2 -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)R 2  2 (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)R 2  2 (10)R 2  2 (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.

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