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- Title
Syntheses, X-ray Crystal Structures and Intermolecular Interaction Patterns of Hydrazone Derivatives with 1,2,3-Triazole Entity at 100 K.
- Authors
Chia, Tze; Quah, Ching; Loh, Wan-Sin; Chandra, Nithin; Kalluraya, Balakrishna; Fun, Hoong-Kun
- Abstract
Five new hydrazone derivatives, ( E)- N′-(4-fluorobenzylidene)-5-methyl-1-(4-nitrophenyl)-1 H-1,2,3-triazole-4-carbohydrazide, ( E)- N′-(4-chlorobenzylidene)-5-methyl-1-(4-nitrophenyl)-1 H-1,2,3-triazole-4-carbohydrazide, ( E)- N′-(4-bromobenzylidene)-5-methyl-1-(4-nitrophenyl)-1 H-1,2,3-triazole-4-carbohydrazide, ( E)- N′-(4-hydroxy-3-methoxybenzylidene)-5-methyl-1-(4-nitrophenyl)-1 H-1,2,3-triazole-4-carbohydrazide and ( E)- N′-(1-(4-bromophenyl)ethylidene)-5-methyl-1-(4-nitrophenyl)-1 H-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 P2/ c, a = 6.8057(1) Å, b = 12.7447(3) Å, c = 18.6936(3) Å, β = 105.356(1)°, B crystallizes in monoclinic P2/ c, a = 8.3815(2) Å, b = 20.8298(4) Å, c = 9.5932(2) Å, β = 99.612(1)°, C crystallizes in monoclinic P2/ c, a = 8.4213(8) Å, b = 21.077(2) Å, c = 9.5899(10) Å, β = 99.979(2)°, D crystallizes in monoclinic P2/ 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.[Figure not available: see fulltext.]
- Subjects
HYDRAZONE derivatives; CRYSTAL structure; INTERMOLECULAR interactions; TRIAZOLES; HYDROGEN bonding; ISOMORPHOUS structures; X-ray crystallography; CHLORINE
- Publication
Journal of Chemical Crystallography, 2014, Vol 44, Issue 4, p220
- ISSN
1074-1542
- Publication type
Article
- DOI
10.1007/s10870-014-0504-8