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Crystal structure and Hirshfeld surface analysis of 1,3-bis-{2,2-di-chloro-1-[(E)-phenyl-diazen-yl]ethen-yl}benzene.

ABSTRACT: In the mol-ecule of the title compound, C₂₂H₁₄Cl₄N₄, the central benzene ring makes dihedral angles of 77.03 (9) and 81.42 (9)° with the two approximately planar 2,2-di-chloro-1-[(E)-phenyl-diazen-yl]vinyl groups. In the crystal, mol-ecules are linked by C-H⋯π, C-Cl⋯π, Cl⋯Cl and Cl⋯H inter-actions, forming a three-dimensional network. The Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H⋯H (30.4%), C⋯H/H⋯C (20.4%), Cl⋯H/H⋯Cl (19.4%), Cl⋯Cl (7.8%) and Cl⋯C/C⋯Cl (7.3%) inter-actions.

SUBMITTER: Shikhaliyev NQ

PROVIDER: S-EPMC8340979 | biostudies-literature |

REPOSITORIES: biostudies-literature

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Crystal structure and Hirshfeld surface analysis of 4-{2,2-di-chloro-1-[(E)-(4-fluoro-phen-yl)diazen-yl]ethen-yl}-N,N-di-methyl-aniline.

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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.

Project description:The crystal structures and Hirshfeld surface analyses of four similar azo compounds are reported. (E)-1-[1-(4-tert-Butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-phenyl-diazene, C18H18Cl2N2, (I), and (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(4-methyl-phen-yl)diazene, C19H20Cl2N2, (II), crystallize in the monoclinic space group C2/c with Z = 8, and (E)-1-[1-(4-tert-butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(4-meth-oxy-phen-yl)diazene, C19H20Cl2N2O, (III), in the monoclinic space group P21/c with Z = 4. (E)-1-[1-(4-tert-Butyl-phen-yl)-2,2-di-chloro-ethen-yl]-2-(3-methyl-phen-yl)diazene, C19H20Cl2N2, (IV), crystallizes in the triclinic space group P with Z = 4 and comprises two mol-ecules (A and B) in the asymmetric unit. In the crystal structures of (I) and (II), mol-ecules are linked by C-H⋯π and C-Cl⋯π inter-actions, forming layers parallel to (02), while mol-ecules of (III) are linked by C-H⋯O contacts, C-H⋯π and C-Cl⋯π inter-actions forming layers parallel to (02). The stability of the mol-ecular packing is ensured by van der Waals forces between these layers. In the crystal structure of (IV), mol-ecules are linked by C-H⋯π and C-Cl⋯π inter-actions, forming a tri-periodic network.

| S-EPMC10439426 | 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.

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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

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