Syntheses, X-ray Crystal Structures and Intermolecular Interaction Patterns of Hydrazone Derivatives with 1,2,3-Triazole Entity at 100 K

Abstract

Five new hydrazone derivatives, (E)-N′-(4-fluorobenzylidene)-5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide, (E)-N′-(4-chlorobenzylidene)-5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide, (E)-N′-(4-bromobenzylidene)-5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide, (E)-N′-(4-hydroxy-3-methoxybenzylidene)-5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide and (E)-N′-(1-(4-bromophenyl)ethylidene)-5-methyl-1-(4-nitrophenyl)-1H-1,2,3-triazole-4-carbohydrazide (denoted as A-E), were prepared and their molecular structures were characterized by single crystal X-ray diffraction. Compound A crystallizes in monoclinic P2₁/c, a = 6.8057(1) Å, b = 12.7447(3) Å, c = 18.6936(3) Å, β = 105.356(1)°, B crystallizes in monoclinic P2₁/c, a = 8.3815(2) Å, b = 20.8298(4) Å, c = 9.5932(2) Å, β = 99.612(1)°, C crystallizes in monoclinic P2₁/c, a = 8.4213(8) Å, b = 21.077(2) Å, c = 9.5899(10) Å, β = 99.979(2)°, D crystallizes in monoclinic P2₁/c, a = 11.1644(10) Å, b = 16.3508(15) Å, c = 9.7313(9) Å, β = 105.757(1)° and E crystallizes in triclinic $P\bar{1}$, a = 8.7415(7) Å, b = 10.1032(8) Å, c = 11.6852(9) Å, α = 68.306(1)°, β = 84.894(1)°, γ = 68.289(1)°. All of the five compounds with close molecular conformations adopt a trans configuration with respect to the hydrazone C = N double bond and weak non-classical intermolecular C–H···O hydrogen bonds are observed in the crystal. Isomorphous substitution between compounds B and C with simple replacement of chlorine atom to bromine atom is giving rise to similar molecular geometries, unit cell parameters and intermolecular interaction pattern of three-dimensional network.

Graphical Abstract

Five new hydrazone derivatives possessing 5-methyl-1-(4-nitrophenyl)-1,2,3-triazole moiety (denoted as A to E) are characterized by single crystal X-ray structure determination method. The intermolecular interaction pattern of D is strongly influenced by strong O–H···O hydrogen bond, whereas only non-classical C–H···O hydrogen bonds are observed in the rest. Compounds B and C with isomorphous chlorine-bromine substitution are crystallized under same space group and similar unit cell parameters.