Crystal structure and DFT study of ( E )-2-chloro-4-{[2-(2,4-dinitrophenyl)hydrazin-1-ylidene]methyl}phenol acetonitrile hemisolvate
2019
The title Schiff base compound, C13H9ClN4O5·0.5CH3CN, crystallizes as an acetonitrile hemisolvate; the solvent molecule being located on a twofold rotation axis. The molecule is nearly planar, with a dihedral angle between the two benzene rings of 3.7 (2)°. The configuration about the C=N bond is E, and there is an intramolecular N—H⋯Onitro hydrogen bond present forming an S(6) ring motif. In the crystal, molecules are linked by O—H⋯O and N—H⋯O hydrogen bonds, forming layers lying parallel to (10\overline{1}). The layers are linked by C—H⋯Cl hydrogen bonds, forming a supramolecular framework. Within the framework there are offset π–π stacking interactions [intercentroid distance = 3.833 (2) A] present involving inversion-related molecules. The DFT study shows that the HOMO and LUMO are localized in the plane extending from the phenol ring to the 2,4-dinitrobenzene ring, and the HOMO–LUMO gap is found to be 0.13061 a.u.
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