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.
Highlights
Acetohydrazides are considered to be good candidates for different pharmaceutical applications, including their use as antibacterial, antifugal, antimicrobial and anticonvulsant agents (Yadav et al, 2015; Bharti et al, 2010; Loncle et al, 2004; Papakonstantinou-Garoufalias et al, 2002)
The thiophene ring is disordered over two sites, corresponding to a rotation about the C3—C6 bond of approximately 180 with population parameters 0.762 (3) for S1A/C1A–C5A and 0.238 (3) for S1B/C1B–C5B (Fig. 1)
The configuration of the C11 N10 bond can be described as E [the N9—N10—C11—C12 torsion angle is 174.82 (16)]
Summary
Acetohydrazides are considered to be good candidates for different pharmaceutical applications, including their use as antibacterial, antifugal, antimicrobial and anticonvulsant agents (Yadav et al, 2015; Bharti et al, 2010; Loncle et al, 2004; Papakonstantinou-Garoufalias et al, 2002). Many of them have shown analgesic and antiplatelet properties (Wardakhan et al, 2013). Combinations of acetohydrazide with other heterocyclic rings have been investigated, such as the hydrazide-based 2-oxonicotinonitrile derivatives that are considered to be potential antimicrobial agents (El-Sayed et al, 2018). As a continuation of our research (Nguyen et al, 2016; Vu et al, 2016, 2017) on the chemical and physical properties of novel polythiophenes, a new thiophene monomer-containing acetohydrazide has been prepared. Symmetry codes: (i) Àx þ 12; y þ 12; z; (ii) x À 12; y; Àz þ 12; (iii) Àx þ 1; Ày þ 1; Àz þ 1; (iv) Àx; y þ 12; Àz þ 12
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