Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene

Abstract

The dihedral angle between the 4-fluoro­phenyl ring and the nitro-substituted benzene ring of the title compound is 63.29 (8)°. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds into chains parallel to the c axis. The crystal packing is further stabilized by C—Cl⋯π, C—F⋯π and N—O⋯π inter­actions

(E)-1-(2,6-Dichlorophenyl)-2-(3-nitrobenzylidene)hydrazine: crystal structure and Hirshfeld surface analysis

“…The title compound was synthesized according to the reported method (Atiog lu et al, 2019;Maharramov et al, 2018). A mixture of 3-nitrobenzaldehyde (10 mmol), CH 3 COONa (0.82 g), ethanol (50 mL) and (2,6-dichlorophenyl)hydrazine (10.2 mmol) was refluxed at 353 K with stirring for 2 h. The reaction mixture was cooled to room temperature and water (50 mL) was added to give a precipitate of the crude product, which was filtered off, washed with diluted ethanol (…”

Crystal structure and Hirshfeld surface analysis of (E)-1-(2,6-dichlorophenyl)-2-(2-nitrobenzylidene)hydrazine

“…The title compound was synthesized according to the reported method (Atiog lu et al, 2019;Maharramov et al, 2018;Shixaliyev et al, 2018Shixaliyev et al, , 2019. A mixture of 2-nitrobenzaldehyde (10 mmol), CH 3 COONa (0.82 g), ethanol (50 mL) and (2,6dichlorophenyl)hydrazine (10.2 mmol) was refluxed at 353 K under stirring for 2 h. The reaction mixture was cooled to room temperature and water (50 mL) was added to give a precipitate of the crude product, which was filtered off, washed with diluted ethanol (1:1 with water) and dried in vacuo using a rotary evaporator.…”

Crystal structure and Hirshfeld surface analysis of (E)-4-{[2,2-dichloro-1-(4-methoxyphenyl)ethenyl]diazenyl}benzonitrile

“…The functionalization of azo/hydrazone ligands with non-covalent bonddonor or acceptor sites greatly affects their coordination ability and the catalytic activity of the corresponding coordination compounds (Akbari et al, 2017;Gurbanov et al, 2018;Karmakar et al, 2016;Kopylovich et al, 2011a,b;Ma et al, 2017a,b;Mahmoudi et al, 2016Mahmoudi et al, , 2017aMahmoudi et al, ,b,c, 2018a. In our previous work, we have attached chloro atoms to dye molecules, which lead to halogen bonding (Atiog lu et al, 2019;Maharramov et al, 2018;Shixaliyev et al, 2018Shixaliyev et al, , 2019. In a continuation of this work, we have functionalized a new azo dye, (E)-4-{[2,2-dichloro-1-(4-methoxyphenyl)ethenyl]diazen-yl}benzonitrile, which provides weak C-HÁ Á ÁO intermolecular hydrogen bonds.…”

“…The title compound was synthesized according to the reported method (Atiog lu et al, 2019;Maharramov et al, 2018;Shikhaliyev et al, 2018Shikhaliyev et al, , 2019. A 20 mL screw-neck vial was charged with DMSO (10 mL), (E)-4-[2-(4-methoxybenzylidene)hydrazineyl]benzonitrile (251 mg, 1 mmol), tetramethylethylenediamine (TMEDA; 295 mg, 2.5 mmol), CuCl (2 mg, 0.02 mmol) and CCl 4 (20 mmol, 10 equiv).…”