Abstract
The complete mol-ecule of the title hydrazine carbodi-thio-ate derivative, C32H30N4O2S4, is generated by a crystallographic twofold axis that bis-ects the di-sulfide bond. The mol-ecule is twisted about this bond with the C-S-S-C torsion angle of 90.70 (8)° indicating an orthogonal relationship between the symmetry-related halves of the mol-ecule. The conformation about the imine bond [1.282 (2) Å] is E and there is limited delocalization of π-electron density over the CN2C residue as there is a twist about the N-N bond [C-N-N-C torsion angle = -166.57 (15)°]. An intra-molecular hydroxyl-O-H⋯N(imine) hydrogen bond closes an S(6) loop. In the crystal, methyl-ene-C-H⋯π(tol-yl) contacts assemble mol-ecules into a supra-molecular layer propagating in the ab plane: the layers stack without directional inter-actions between them. The analysis of the calculated Hirshfeld surfaces confirm the importance of H⋯H contacts, which contribute 46.7% of all contacts followed by H⋯C/C⋯H contacts [25.5%] reflecting, in part, the C-H⋯π(tol-yl) contacts. The calculation of the inter-action energies confirm the importance of the dispersion term and the influence of the stabilizing H⋯H contacts in the inter-layer region.
Highlights
The crystallographic asymmetric unit of (I) comprises half a molecule as it is disposed about a twofold axis of symmetry bisecting the disulfide bond, Fig. 1
The sequence of C1 N1 (E-conformation), N1—N2 and C2 N2 bond lengths is 1.282 (2), 1.409 (2) and 1.286 (2) A, respectively, and suggests limited delocalization of -electron density over this residue which is consistent with a twist about the N1—N2 bond as seen in the C1—N1—N2—C2 torsion angle of À166.57 (15)
Note: (a) The interatomic distances are calculated in Crystal Explorer 17 (Turner et al, 2017) with the X—H bond lengths adjusted to their neutron values
Summary
Schiff base molecules can be derived from the condensation of S-alkyl-dithiocarbazate derivatives with heterocyclic aldehydes and ketones to form molecules of the general formula RSC( S)N(H)N C(R0)R00, where R0, R00 = alkyl and aryl These molecules are effective ligands for a variety of metals and the motivation for complexation largely stems from the promising biological activity exhibited by the derived metal complexes (Low et al, 2016; Ravoof et al, 2017; Yusof et al, 2020). These Schiff bases are susceptible to oxidation resulting in the formation of a disulfide bond, as has been observed previously (Amirnasr et al, 2014; Sohtun et al, 2018).
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