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Crystal Structure and Hirshfeld Surface Analysis of (E)-1-(4-Bromophenyl)-2-(2,2-Dichloro-1-(4-Fluorophenyl)vinyl)diazene

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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.

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ACKNOWLEDGMENTS

This work was supported by the Science Development Foundation under the President of the Republic of Azerbaijan (Grant no. EİF-BGM-4-RFTF-1/2017-21/13/4). Iván Brito, Alejandro Cárdenas and Jonathan Cisterna, thank Universidad de Antofagasta for purchasing a license for the Cambridge Structural Database and financial support. Jonathan Cisterna acknowledges Universidad de Antofagasta for postdoctoral fellowship.

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Authors and Affiliations

  1. Organic Chemistry Department, Baku State University, AZ 1148, Baku, Azerbaijan

    N. Q. Shikhaliyev, K. N. Bagirova, A. A. Niyazova & G. Z. Mammadova

  2. Departamento de Química, Facultad de Ciencias Básicas, Universidad de Antofagasta, Avda, Campus Coloso, 02800, Antofagasta, Chile

    J. Cisterna & I. Brito

  3. Departamento de Física, Facultad de Ciencias Básicas, Universidad de Antofagasta, Avda, Campus Coloso, 02800, Antofagasta, Chile

    A. Cárdenas

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  1. N. Q. Shikhaliyev
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  2. K. N. Bagirova
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  3. A. A. Niyazova
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  4. G. Z. Mammadova
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  5. J. Cisterna
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  6. A. Cárdenas
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  7. I. Brito
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Correspondence to I. Brito.

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Shikhaliyev, N.Q., Bagirova, K.N., Niyazova, A.A. et al. Crystal Structure and Hirshfeld Surface Analysis of (E)-1-(4-Bromophenyl)-2-(2,2-Dichloro-1-(4-Fluorophenyl)vinyl)diazene. Crystallogr. Rep. 65, 1169–1172 (2020). https://doi.org/10.1134/S1063774520070214

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  • DOI: https://doi.org/10.1134/S1063774520070214

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