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

ABSTRACT: The asymmetric unit of the title compound, C₁₆H₁₄Cl₂N₂O, comprises two similar mol-ecules, A and B, in which the dihedral angles between the two aromatic rings are 70.1 (3) and 73.2 (2)°, respectively. The crystal structure features short C-H⋯Cl and C-H⋯O contacts and C-H⋯π and van der Waals inter-actions. The title compound was refined as a two-component non-merohedral twin, BASF 0.1076 (5). The Hirshfeld surface analysis and two-dimensional fingerprint plots show that H⋯H (38.2% for mol-ecule A; 36.0% for mol-ecule B), Cl⋯H/H⋯Cl (24.6% for mol-ecule A; 26.7% for mol-ecule B) and C⋯H/H⋯C (20.0% for mol-ecule A; 20.2% for mol-ecule B) inter-actions are the most important contributors to the crystal packing.

SUBMITTER: Shikhaliyev NQ

PROVIDER: S-EPMC8423004 | biostudies-literature |

REPOSITORIES: biostudies-literature

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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 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.

| S-EPMC6509676 | biostudies-literature

Crystal structure and Hirshfeld surface analysis of (E)-4-{[2,2-di-chloro-1-(4-meth-oxy-phen-yl)ethen-yl]diazen-yl}benzo-nitrile.

Project description:In the title compound, C16H11Cl2N3O, the 4-meth-oxy-substituted benzene ring makes a dihedral angle of 41.86 (9)° with the benzene ring of the benzo-nitrile group. In the crystal, mol-ecules are linked into layers parallel to (020) by C-H⋯O contacts and face-to-face π-π stacking inter-actions [centroid-centroid distances = 3.9116 (14) and 3.9118 (14) Å] between symmetry-related aromatic rings along the a-axis direction. A Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from Cl⋯H/H⋯Cl (22.8%), H⋯H (21.4%), N⋯H/H⋯N (16.1%), C⋯H/H⋯C (14.7%) and C⋯C (9.1%) inter-actions.

| S-EPMC6690439 | biostudies-literature

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.

Project description: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.

| S-EPMC6362658 | biostudies-literature

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.

| S-EPMC9260355 | biostudies-literature

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.

| S-EPMC9069519 | biostudies-literature

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.

| S-EPMC8983971 | biostudies-literature

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.

Project description:In the title compound, C16H14Cl2FN3, the dihedral angle between the two aromatic rings is 64.12?(14)°. The crystal structure is stabilized by a short Cl?H contact, C-Cl?? and van der Waals inter-actions. The Hirshfeld surface analysis and two-dimensional fingerprint plots show that H?H (33.3%), Cl?H/H?Cl (22.9%) and C?H/H?C (15.5%) inter-actions are the most important contributors towards the crystal packing.

| S-EPMC7274008 | biostudies-literature

1-(2-Meth-oxy-phen-yl)-2-{[2-(2-meth-oxy-phen-yl)hydrazinyl-idene](nitro)-meth-yl}diazene.

Project description:In the title compound, C(15)H(15)N(5)O(4), a nitro-formazan derivative, the formazan unit is essentially planar with an r.m.s. deviation of 0.0204?(6)?Å and adopts a closed syn,s-cis configuration with an intra-molecular N-H?N hydrogen bond. The formazan plane makes dihedral angles of 4.32?(5) and 24.35?(5)° with the benzene rings. The dihedral angle between the formazan plane and the nitro group is 12.58?(8)°. In the crystal, C-H?O inter-actions connect the mol-ecules into an inversion dimer.

| S-EPMC3295411 | biostudies-literature

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