2-[(1 E )-[( Z )-2-({[(1 Z )-[( E )-2-[(2-Hydroxyphenyl)methylidene]hydrazin-1-ylidene]({[(4-methylphenyl)methyl]sulfanyl})methyl]disulfanyl}({[(4-methylphenyl)methyl]sulfanyl})methylidene)hydrazin-1-ylidene]methyl]phenol: crystal structure, Hirshfeld surface analysis and computational study

• Published in: Acta crystallographica. Section E, Crystallographic communications Crystallographic communications, 2020-08, Vol.76 (8), p.1245-1250
• Main Authors: Paulus, Georgiana, Kwong, Huey Chong, Crouse, Karen A., Tiekink, Edward R. T.
• Format: Article
• Language: English
• Subjects: crystal structure; dft; hirshfeld surface analysis; hydrazine carbodithioate; hydrogen bonding; schiff base
• ISSN: 2056-9890; 2056-9890
• DOI: 10.1107/S2056989020008762

The complete molecule of the title hydrazine carbodithioate derivative, C 32 H 30 N 4 O 2 S 4 , is generated by a crystallographic twofold axis that bisects the disulfide bond. The molecule 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 molecule. The conformation about the imine bond [1.282 (2) Å] is E and there is limited delocalization of π-electron density over the CN 2 C residue as there is a twist about the N—N bond [C—N—N—C torsion angle = −166.57 (15)°]. An intramolecular hydroxyl-O—H...N(imine) hydrogen bond closes an S (6) loop. In the crystal, methylene-C—H...π(tolyl) contacts assemble molecules into a supramolecular layer propagating in the ab plane: the layers stack without directional interactions 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(tolyl) contacts. The calculation of the interaction energies confirm the importance of the dispersion term and the influence of the stabilizing H...H contacts in the inter-layer region.