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Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-di-chloro-1-(4-nitro-phen-yl)ethen-yl]-2-(4-fluoro-phen-yl)diazene.

ABSTRACT: In the title compound, C₁₄H₈Cl₂FN₃O₂, the 4-fluoro-phenyl ring and the nitro-substituted benzene ring form a dihedral angle of 63.29?(8)°. In the crystal, mol-ecules are linked by C-H?O hydrogen bonds into chains running parallel to the c axis. The crystal packing is further stabilized by C-Cl??, C-F?? and N-O?? inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H?O/O?H (15.5%), H?H (15.3%), Cl?H/H?Cl (13.8%), C?H/H?C (9.5%) and F?H/H?F (8.2%) inter-actions.

SUBMITTER: Atioglu Z

PROVIDER: S-EPMC6362658 | biostudies-literature | 2019 Feb

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-di-chloro-1-(4-nitro-phen-yl)ethen-yl]-2-(4-fluoro-phen-yl)diazene.

Atioğlu Zeliha Z Akkurt Mehmet M Shikhaliyev Namiq Q NQ Suleymanova Gulnar T GT Bagirova Khanim N KN Toze Flavien A A FAA

Acta crystallographica. Section E, Crystallographic communications 20190118 Pt 2

In the title compound, C14H8Cl2FN3O2, the 4-fluoro-phenyl ring and the nitro-substituted benzene ring form a dihedral angle of 63.29 (8)°. In the crystal, mol-ecules are linked by C-H⋯O hydrogen bonds into chains running parallel to the c axis. The crystal packing is further stabilized by C-Cl⋯π, C-F⋯π and N-O⋯π inter-actions. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to th ...[more]

PMID: 30800458

Similar Datasets

Crystal structures and Hirshfeld surface analyses of the two isotypic compounds (E)-1-(4-bromo-phen-yl)-2-[2,2-di-chloro-1-(4-nitro-phen-yl)ethen-yl]diazene and (E)-1-(4-chloro-phen-yl)-2-[2,2-di-chloro-1-(4-nitro-phen-yl)ethen-yl]diazene.

Project description:In the two isotypic title compounds, C14H8BrCl2N3O2, (I), and C14H8Cl3N3O2, (II), the substitution of one of the phenyl rings is different [Br for (I) and Cl for (II)]. Aromatic rings form dihedral angles of 60.9 (2) and 64.1 (2)°, respectively. Mol-ecules are linked through weak X⋯Cl contacts [X = Br for (I) and Cl for (II)], C-H⋯Cl and C-Cl⋯π inter-actions into sheets parallel to the ab plane. Additional van der Waals inter-actions consolidate the three-dimensional packing. Hirshfeld surface analysis of the crystal structures indicates that the most important contributions for the crystal packing for (I) are from C⋯H/H⋯C (16.1%), O⋯H/H⋯O (13.1%), Cl⋯H/H⋯Cl (12.7%), H⋯H (11.4%), Br⋯H/H⋯Br (8.9%), N⋯H/H⋯N (6.9%) and Cl⋯C/C⋯Cl (6.6%) inter-actions, and for (II), from Cl⋯H / H⋯Cl (21.9%), C⋯H/H⋯C (15.3%), O⋯H/H⋯O (13.4%), H⋯H (11.5%), Cl⋯C/C⋯Cl (8.3%), N⋯H/H⋯N (7.0%) and Cl⋯Cl (5.9%) inter-actions. The crystal of (I) studied was refined as an inversion twin, the ratio of components being 0.9917 (12):0.0083 (12).

| S-EPMC6690453 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chloro-phen-yl)-2-[2,2-di-chloro-1-(4-fluoro-phen-yl)ethen-yl]diazene.

Project description:In the title compound, C14H8Cl3FN2, the planes of the 4-fluoro-phenyl ring and the 4-chloro-phenyl ring make a dihedral angle of 56.13 (13)°. In the crystal, mol-ecules are stacked in a column along the a axis via a weak C-H⋯Cl hydrogen bond and face-to-face π-π stacking inter-actions [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%) inter-actions.

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Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-di-bromo-1-(4-nitro-phen-yl)ethen-yl]-2-(4-fluoro-phen-yl)diazene.

Project description:In the title compound, C14H8Br2FN3O2, the 4-fluoro-phenyl ring and the nitro-substituted phenyl ring form a dihedral angle of 64.37 (10)°. Mol-ecules in the crystal are connected by C-H⋯O and C-H⋯F hydrogen bonds into layers parallel to (011). The crystal packing is consolidated by C-Br⋯π and C-F⋯π inter-actions, as well as by π-π stacking inter-actions. According to a Hirshfeld surface analysis of the crystal structure, the most significant contributions to the crystal packing are from O⋯H/H⋯O (15.0%), H⋯H (14.3%), Br⋯H/H⋯Br (14.2%), C⋯H/H⋯C (10.1%), F⋯H/H⋯F (7.9%), Br⋯Br (7.2%) and Br⋯C/C⋯Br (5.8%) contacts.

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Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-di-bromo-1-(2-nitro-phen-yl)ethen-yl]-2-(4-fluoro-phen-yl)diazene.

Project description:In the title compound, C14H8Br2FN3O2, the nitro-substituted benzene ring and the 4-fluoro-phenyl ring form a dihedral angle of 65.73 (7)°. In the crystal, mol-ecules are linked into chains by C-H⋯O hydrogen bonds running parallel to the c-axis direction. The crystal packing is consolidated by C-F⋯π inter-actions and π-π stacking inter-actions, and short Br⋯O [2.9828 (13) Å] contacts are observed. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H⋯H (17.4%), O⋯H/H⋯O (16.3%), Br⋯H/H⋯Br (15.5%), Br⋯C/C⋯Br (10.1%) and F⋯H/H⋯F (8.1%) contacts.

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Crystal structures and Hirshfeld surface analyses of (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-phenyl-diazene, (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(4-methyl-phen-yl)diazene, (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(4-meth-oxy-phen-yl)diazene and (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(3-methyl-phen-yl)diazene.

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Crystal structure and Hirshfeld surface analysis of (E)-2-(4-bromo-phen-yl)-1-[2,2-di-bromo-1-(4-nitro-phen-yl)ethen-yl]diazene.

Project description:The mol-ecule of the title compound, C14H8Br3N3O2, consists of three almost planar groups: the central di-bromo-ethenyldiazene fragment and two attached aromatic rings. The mean planes of these rings form dihedral angles with the plane of the central fragment of 26.35 (15) and 72.57 (14)° for bromine- and nitro-substituted rings, respectively. In the crystal, C-H⋯Br inter-actions connect mol-ecules, generating zigzag C(8) chains along the [100] direction. These chains are linked by C-Br⋯π inter-actions into layers parallel to (001). van der Waals inter-actions between the layers aid in the cohesion of the crystal packing. The most substantial contributions to crystal packing, according to a Hirshfeld surface analysis, are from Br⋯H/H⋯Br (20.9%), C⋯H/H⋯C (15.2%), O⋯H/H⋯O (12.6%) and H⋯H (11.7%) contacts.

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N-(5-Chloro-2-nitro-phen-yl)-2,2-di-methyl-propanamide.

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