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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 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).

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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.

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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.

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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)-4-{2,2-di-chloro-1-[(3,5-di-methyl-phen-yl)diazen-yl]ethen-yl}-N,N-di-methyl-aniline.

Project description:In the title compound, C18H19Cl2N3, the planes of the benzene rings subtend a dihedral angle of 77.07?(10)°. In the crystal, mol-ecules are associated into inversion dimers via short Cl?Cl contacts [3.3763?(9)?Å]. A Hirshfeld surface analysis indicates that the most important contact percentages for the different types of inter-actions are H?H (43.9%), Cl?H/H?Cl (22.9%), C?H/H?C (20.8%) and N?H/H?N (8.0%).

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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.

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.

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

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

Project description:In the tile compound, C17H17Cl2N3, the dihedral angle between the benzene rings is 62.73?(9)°. In the crystal, there are no classical hydrogen bonds. Mol-ecules are linked by a pair of C-Cl?? inter-actions, forming an inversion dimer. A short inter-molecular HL?HL contact [Cl?Cl = 3.2555?(9)?Å] links the dimers, forming a ribbon along the c-axis direction. The Hirshfeld surface analysis and two-dimensional fingerprint plots reveal that the most important contributions for the crystal packing are from H?H (45.4%), Cl?H/H?Cl (21.0%) and C?H/H?C (19.0%) contacts.

| S-EPMC7336769 | biostudies-literature

4-(4-Chloro-phen-yl)-6-meth-oxy-2,2'-bipyridine-5-carbonitrile.

Project description:There are two independent mol-ecules in the asymmetric unit of the title compound, C(18)H(12)ClN(3)O. The two pyridine rings are almost coplanar [dihedral angles between the rings: 2.87?(15) and 5.36?(16)°] while the chloro-phenyl rings are twisted out of the plane of the adjacent bipyridine ring by 44.1?(1) and 43.8?(1)° in the two mol-ecules. The crystal packing is stabilized by C-H?N and C-H?Cl inter-actions.

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