Title of article :
2-[(1E)-[(Z)-2-({[(1Z)-[(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
Author/Authors :
Paulus, Georgiana Department of Chemistry - Faculty of Science - Universiti Putra Malaysia, Malaysia , Kwong, Huey Chong Department of Chemistry - Faculty of Science - Universiti Putra Malaysia, Malaysia , Crouse, Karen A. Department of Chemistry - Faculty of Science - Universiti Putra Malaysia, Malaysia , Tiekink, Edward R. T. Research Centre for Crystalline Materials - School of Science and Technology - Sunway University, Malaysia
Abstract :
The complete molecule of the title hydrazine carbodithioate derivative, C32H30N4O2S4, 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 CN2C 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.
Keywords :
Schiff base , hydrazine carbodithioate , hydrogen bonding , Hirshfeld surface analysis , DFT , crystal structure
Journal title :
Acta Crystallographica Section E: Crystallographic Communications