Abstract
The compound N-[2-(4-fluoro-3-phen-oxy-benzo-yl)hydrazinecarbo-thio-yl]benzamide, C21H16FN3O3S, crystallizes in the monoclinic centrosymmetric space group P21/c and its mol-ecular conformation is stabilized via an intra-molecular N-H⋯O hydrogen bond. The corresponding para-meth-oxy derivative, namely, N-[2-(4-fluoro-3-phen-oxy-benzo-yl)hydrazinecarbo-thio-yl]-4-meth-oxy-benzamide, C22H18FN3O4S, crystallizes in the monoclinic centrosymmetric space group C2/c. The supra-molecular network mainly comprises N-H⋯O, N-H⋯S and C-H⋯O hydrogen bonds, which contribute towards the formation of the crystal structures for the two mol-ecules. The different inter-molecular inter-actions have been further analysed using Hirshfeld surface analysis and fingerprint plots.
Highlights
The compound N-[2-(4-fluoro-3-phenoxybenzoyl)hydrazinecarbothioyl]benzamide, C21H16FN3O3S, crystallizes in the monoclinic centrosymmetric space group P21/c and its molecular conformation is stabilized via an intramolecular N—HÁ Á ÁO hydrogen bond
The supramolecular network mainly comprises N— HÁ Á ÁO, N—HÁ Á ÁS and C—HÁ Á ÁO hydrogen bonds, which contribute towards the formation of the crystal structures for the two molecules
Piperidin-4-yl-based TSCs have been examined for cytotoxicity in breast cancer cell lines in addition to being possible potential topoisomerase inhibitors (Siwek et al, 2014). 1-(2-Hydroxybenzoyl)-thiosemicarbazides have been observed to exhibit antimicrobial activity and structure– activity relationship (SARs) studies establish that the 2-hydroxybenzoyl group plays an important role in enzyme inhibition, in addition to these exhibiting low cytotoxicity (Ameryckx et al, 2018)
Summary
Substituted thiosemicarbazides (TSCs) constitute an important class of organic compounds with the general formula R– (C O)–NH–NH–(C S)–R0 and find application in the synthesis of five- and six-membered heterocyclic compounds (Gazieva & Kravchenko, 2012) and transition-metal complexes (Campbell, 1975). Molecular modelling studies establish the relevance of both geometry and electrondensity distribution in the observed antibacterial activity (Paneth et al, 2016). 1-(2-Hydroxybenzoyl)-thiosemicarbazides have been observed to exhibit antimicrobial activity and structure– activity relationship (SARs) studies establish that the 2-hydroxybenzoyl group plays an important role in enzyme inhibition, in addition to these exhibiting low cytotoxicity (Ameryckx et al, 2018). Keeping in mind the abovementioned applications of substituted TSCs, we have performed the synthesis and crystal structure analysis of two compounds, namely N-[2-(4-fluoro-3-phenoxybenzoyl)-. The molecular structure comprises one fluoro-substituted phenoxybenzoyl ring, a rigid and planar (C O)—NH—NH—(C S) moiety and a benzamide ring. The molecular structure possesses four conformational degrees of freedom due to the free rotation with respect to the N1—N2, C7—O1, O1—C1 and C15—C16 single bonds. Symmetry codes: (i) Àx þ 1; y; Àz þ 12; (ii) x; y þ 1; z; (iii) Àx þ 1; Ày À 1; Àz
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