Abstract
In the title hydrazinecarbodi-thio-ate derivative, C27H26N2O2S2, the asymmetric unit is comprised of four mol-ecules (Z = 8 and Z' = 4). The 4-meth-oxy-phenyl rings are slightly twisted away from their attached olefinic double bonds [torsion angles = 5.9 (4)-19.6 (4)°]. The azomethine double bond has an s-trans configuration relative to one of the C=C bonds and an s-cis configuration relative to the other [C=C-C= N = 147.4 (6)-175.7 (2) and 15.3 (3)-37.4 (7)°, respectively]. The torsion angles between the azomethine C=N double bond and hydrazine-1-carbodi-thio-ate moiety indicate only small deviations from planarity, with torsion angles ranging from 0.9 (3) to 6.9 (3)° and from 174.9 (3) to 179.7 (2)°, respectively. The benzyl ring and the methyl-enesulfanyl moiety are almost perpendicular to each other, as indicated by their torsion angles [range 93.7 (3)-114.6 (2)°]. In the crystal, mol-ecules are linked by C-H⋯O, N-H⋯S and C-H⋯π(ring) hydrogen-bonding inter-actions into a three-dimensional network. Structural details of related benzyl hydrazine-1-carbodi-thio-ate are surveyed and compared with those of the title compound.
Highlights
Encouraged by previous findings on various properties of related Schiff base derivatives, we report the synthesis and structure determination of the title compound (I)
The molecules are composed of a 1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-ylidenyl moiety, connected to a benzyl ring by a hydrazine-1-carbodithioate (–C N—(NH)— (C S)—S—C–) bridge (Fig. 1)
Conformational details of the 1,5-bis(4-methoxyphenyl)penta-1,4-dien-3-ylidenyl moiety can be described by the torsion angles between the 4-methoxy moiety and the phenyl ring [1 (C2—C3—O1—C26); 6 (C16—C15—O2—C27)], between the 4-methoxyphenyl ring and the olefinic double bond [2 (C5—C6-C7—C8); 5 (C17— C12—C11—C10)], and between the olefinic double bond and the azomethine double bond [3 (N1—C9—C8—C7); 4 (N1— C9—C10—C11)]
Summary
S-benzyl and S-alkyl dithiocarbazates are interesting ligands in coordination chemistry because they can act as N,S-chelating agents because of the presence of soft sulfur and hard nitrogen donor atoms (Takjoo et al, 2016). These types of ligands can form stable metal complexes with five-membered chelate rings, and with transition metals in different stable oxidation states (Centore et al, 2013). Dithiocarbazate Schiff bases and their metal complexes show a wide range of biological activities such as anti-malarial, anti-bacterial, anti-viral and antitumour (Low et al, 2016; Nanjundan et al, 2016; Islam et al, 2016a).
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