Crystal structure of two N'-(1-phenyl-benzyl-idene)-2-(thio-phen-3-yl)acetohydrazides.

ABSTRACT: The synthesis, spectroscopic data, crystal and mol-ecular structures of two N'-(1-phenyl-benzyl-idene)-2-(thio-phen-3-yl)acetohydrazides, namely N'-[1-(4-hy-droxy-phen-yl)benzyl-idene]-2-(thio-phen-3-yl)acetohydrazide, C₁₃H₁₀N₂O₂S, (3a), and N'-[1-(4-meth-oxy-phen-yl)benzyl-idene]-2-(thio-phen-3-yl)acetohydrazide, C₁₄H₁₄N₂O₂S, (3b), are described. Both compounds differ in the substituent at the para position of the phenyl ring: -OH for (3a) and -OCH₃ for (3b). In (3a), the thio-phene ring is disordered over two orientations with occupancies of 0.762?(3) and 0.238?(3). The configuration about the C=N bond is E. The thio-phene and phenyl rings are inclined by 84.0?(3) and 87.0?(9)° for the major- and minor-occupancy disorder components in (3a), and by 85.89?(12)° in (3b). Although these dihedral angles are similar, the conformation of the linker between the two rings is different [the C-C-C-N torsion angle is -ac for (3a) and -sc for (3b), while the C6-C7-N9-N10 torsion angle is +ap for (3a) and -sp for (3b)]. A common feature in the crystal packing of (3a) and (3b) is the presence of N-H?O hydrogen bonds, resulting in the formation of chains of mol-ecules running along the b-axis direction in the case of (3a), or inversion dimers for (3b). The most prominent contributions to the surface contacts are those in which H atoms are involved, as confirmed by an analysis of the Hirshfeld surface.

SUBMITTER: Vu Quoc T 

PROVIDER: S-EPMC6690450 | biostudies-literature | 2019 Aug

REPOSITORIES: biostudies-literature