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

In the title compound, C(14)H(8)Cl(3)FN(2), the planes of the 4-fluoro­phenyl ring and the 4-chloro­phenyl ring make a dihedral angle of 56.13 (13)°. In the crystal, mol­ecules are stacked in a column along the a axis via a weak C—H⋯Cl hydrogen bond and face-to-face π–π stacking inter­actions [centr...

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Autores principales: Shikhaliyev, Namiq Q., Çelikesir, Sevim Türktekin, Akkurt, Mehmet, Bagirova, Khanim N., Suleymanova, Gulnar T., Toze, Flavien A. A.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: International Union of Crystallography 2019
Materias:
Research Communications
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6509676/
https://www.ncbi.nlm.nih.gov/pubmed/31161058
http://dx.doi.org/10.1107/S2056989019003657
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author Shikhaliyev, Namiq Q.
Çelikesir, Sevim Türktekin
Akkurt, Mehmet
Bagirova, Khanim N.
Suleymanova, Gulnar T.
Toze, Flavien A. A.
author_facet Shikhaliyev, Namiq Q.
Çelikesir, Sevim Türktekin
Akkurt, Mehmet
Bagirova, Khanim N.
Suleymanova, Gulnar T.
Toze, Flavien A. A.
author_sort Shikhaliyev, Namiq Q.
collection PubMed
description In the title compound, C(14)H(8)Cl(3)FN(2), the planes of the 4-fluoro­phenyl ring and the 4-chloro­phenyl ring make a dihedral angle of 56.13 (13)°. In the crystal, mol­ecules are stacked in a column along the a axis via a weak C—H⋯Cl hydrogen bond and face-to-face π–π stacking inter­actions [centroid–centroid distances = 3.8615 (18) and 3.8619 (18) Å]. The crystal packing is further stabilized by short Cl⋯Cl contacts. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from Cl⋯H/H⋯Cl (31.2%), H⋯H (14.8%), C⋯H/H⋯C (14.0%), F⋯H/H⋯F (12.8%), C⋯C (9.0%) and Cl⋯Cl (6.7%) inter­actions.
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spelling pubmed-65096762019-06-03 Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-fluoro­phen­yl)ethen­yl]diazene Shikhaliyev, Namiq Q. Çelikesir, Sevim Türktekin Akkurt, Mehmet Bagirova, Khanim N. Suleymanova, Gulnar T. Toze, Flavien A. A. Acta Crystallogr E Crystallogr Commun Research Communications In the title compound, C(14)H(8)Cl(3)FN(2), the planes of the 4-fluoro­phenyl ring and the 4-chloro­phenyl ring make a dihedral angle of 56.13 (13)°. In the crystal, mol­ecules are stacked in a column along the a axis via a weak C—H⋯Cl hydrogen bond and face-to-face π–π stacking inter­actions [centroid–centroid distances = 3.8615 (18) and 3.8619 (18) Å]. The crystal packing is further stabilized by short Cl⋯Cl contacts. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from Cl⋯H/H⋯Cl (31.2%), H⋯H (14.8%), C⋯H/H⋯C (14.0%), F⋯H/H⋯F (12.8%), C⋯C (9.0%) and Cl⋯Cl (6.7%) inter­actions. International Union of Crystallography 2019-03-26 /pmc/articles/PMC6509676/ /pubmed/31161058 http://dx.doi.org/10.1107/S2056989019003657 Text en © Shikhaliyev et al. 2019 http://creativecommons.org/licenses/by/4.0/ This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.http://creativecommons.org/licenses/by/4.0/
spellingShingle Research Communications
Shikhaliyev, Namiq Q.
Çelikesir, Sevim Türktekin
Akkurt, Mehmet
Bagirova, Khanim N.
Suleymanova, Gulnar T.
Toze, Flavien A. A.
Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-fluoro­phen­yl)ethen­yl]diazene
title Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-fluoro­phen­yl)ethen­yl]diazene
title_full Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-fluoro­phen­yl)ethen­yl]diazene
title_fullStr Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-fluoro­phen­yl)ethen­yl]diazene
title_full_unstemmed Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-fluoro­phen­yl)ethen­yl]diazene
title_short Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-fluoro­phen­yl)ethen­yl]diazene
title_sort crystal structure and hirshfeld surface analysis of (e)-1-(4-chloro­phen­yl)-2-[2,2-di­chloro-1-(4-fluoro­phen­yl)ethen­yl]diazene
topic Research Communications
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6509676/
https://www.ncbi.nlm.nih.gov/pubmed/31161058
http://dx.doi.org/10.1107/S2056989019003657
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