Abstract
The title Schiff base compound, C13H9ClN4O5·0.5CH3CN, crystallizes as an aceto-nitrile hemisolvate; the solvent mol-ecule being located on a twofold rotation axis. The mol-ecule 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 intra-molecular N-H⋯Onitro hydrogen bond present forming an S(6) ring motif. In the crystal, mol-ecules are linked by O-H⋯O and N-H⋯O hydrogen bonds, forming layers lying parallel to (10). The layers are linked by C-H⋯Cl hydrogen bonds, forming a supra-molecular framework. Within the framework there are offset π-π stacking inter-actions [inter-centroid distance = 3.833 (2) Å] present involving inversion-related mol-ecules. The DFT study shows that the HOMO and LUMO are localized in the plane extending from the phenol ring to the 2,4-di-nitro-benzene ring, and the HOMO-LUMO gap is found to be 0.13061 a.u.
Highlights
Over the past 25 years, extensive research has surrounded the synthesis and use of Schiff base compounds in organic and inorganic chemistry, as they have important medicinal and pharmaceutical applications
Schiff bases are becoming increasingly important in the dye and plastics industries as well as for liquid-crystal technology and the mechanistic investigation of drugs used in pharmacology, biochemistry and physiology (Sheikhshoaie & Sharif, 2006). 2,4-Dinitrophenylhydrazine is frequently used as a reagent for the characterization of aldehydes and ketones (Furniss et al, 1999)
We report on the synthesis, crystal structure and density functional theory (DFT) computational calculations of the title new Schiff base compound
Summary
Over the past 25 years, extensive research has surrounded the synthesis and use of Schiff base compounds in organic and inorganic chemistry, as they have important medicinal and pharmaceutical applications. These compounds show biological activities including antibacterial, antifungal, anticancer and herbicidal activities (Desai et al, 2001; Singh & Dash, 1988; Karia & Parsania, 1999). Its derivatives are widely used as dyes (Guillaumont & Nakamura, 2000) They are found to have versatile coordinating abilities towards different metal ions (Raj & Kurup, 2007). We report on the synthesis, crystal structure and DFT computational calculations of the title new Schiff base compound. Symmetry codes: (i) x þ 12; Ày þ 32; z þ 12; (ii) Àx þ 32; Ày þ 12; Àz þ 1; (iii) Àx þ 1; Ày þ 2; Àz þ 1
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