Crystal Structure and Hirshfeld Surface Analysis of ( E )-1-(4-Bromophenyl)-2-(2,2-Dichloro-1-(4-Fluorophenyl)vinyl)diaz
- PDF / 826,578 Bytes
- 4 Pages / 612 x 792 pts (letter) Page_size
- 96 Downloads / 210 Views
TRUCTURE OF ORGANIC COMPOUNDS
Crystal Structure and Hirshfeld Surface Analysis of (E)-1-(4-Bromophenyl)-2-(2,2-Dichloro-1(4-Fluorophenyl)vinyl)diazene N. Q. Shikhaliyeva, K. N. Bagirovaa, A. A. Niyazovaa, G. Z. Mammadovaa, J. Cisternab, A. Cárdenasc, and I. Britob,* a
b
Organic Chemistry Department, Baku State University, Baku, AZ 1148 Azerbaijan Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Avda, Campus Coloso, Antofagasta, 02800 Chile c Departamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta, Avda, Campus Coloso, Antofagasta, 02800 Chile *e-mail: [email protected] Received April 18, 2019; revised March 11, 2020; accepted March 17, 2020
Abstract—The CuCl-catalyzed olefination with CCl4 in the presence of tetramethylethylenediamine in DMSO leads to the formation of (E)-1-(4-bromo-(2,2-dichloro-1-(4-fluorophenyl)vinyl)-diazene from (E)-1-(4-bromophenyl)-2-(4-fluorobenzylidene)hydrazine. The structure was confirmed by conventional spectroscopy techniques (nuclear magnetic resonance, electrospray ionization mass spectrometry) and determined by X-ray diffraction analysis of single crystals. The title compound crystallized in a monoclinic cell (space group P21/c, Z = 4) with a centrosymmetric arrangement of molecules in the crystal structure, showing interesting non-covalent interactions that were studied by Hirshfeld surface analysis. DOI: 10.1134/S1063774520070214
INTRODUCTION Dyes and their complexes attract much attention due to their high synthetic potential for organic and inorganic chemistry, analytical and catalytic properties [1–9]. For example, azo-hydrazone dyes are among the most examined colouring and signalling systems due to their controllable E/Z isomerization around the N=N or C=N double bond, what makes them good candidates for creating molecular electronics devices, switches, rotors and similar nanomachines [10–13]. The chemical and physical properties of dyes strongly depend on intra- and intermolecular noncovalent interactions [14–17]. We report here about the crystal and molecular structure and intermolecular halogen and hydrogen bonds in (E)-1-(4-bromophenyl)-2-(2,2-dichloro-1-(4-fluorophenyl)vinyl)diazene (1) (Scheme 1). Cl
Cl N
F
N
1 Scheme 1.
Br
EXPERIMENTAL Synthesis This dye was synthesized according to the procedure [14]. DMSO (10 mL), (E)-1-(4-bromophenyl)2-(4-fluorobenzylidene)hydrazine (248 mg, 1 mmol), tetramethylethylenediamine (TMEDA) (295 mg, 2.5 mmol), CuCl (2 mg, 0.02 mmol), and CCl4 (20 mmol, 10 equiv.) were loaded into a 20 mL screw neck vial. After 1–3 h (until analysis by thin layer chromatography showed complete consumption of corresponding Schiff base), the reaction mixture was poured into ∼0.01 M solution of HCl (100 mL, ∼pH 2–3), and extracted with dichloromethane (3 × 20 mL). The combined organic phase was washed with water (3 × 50 mL), brine (30 mL), dried over anhydrous Na2SO4 and concentrated in vacuo of a rotary evaporator. The residue was purified by silica gel column chromatography using appropr
Data Loading...
