Crystal structure and Hirshfeld surface analysis of a new polymorph of (<i>E</i>)-2-(4-bromophenyl)-1-[2,2-dibromo-1-(3-nitrophenyl)ethenyl]diazene

Atioğlu, Zeliha; Akkurt, Mehmet; Shikhaliyev, Namiq Q.; Mammadova, Naila A.; Babayeva, Gulnara V.; Хрусталев, В. Н.; Bhattarai, Ajaya

doi:10.1107/s2056989022007113

Cited by 3 publications

(1 citation statement)

References 32 publications

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“…A search of the Cambridge Structural Database [27] for similar structures with the (E)-1-(2,2-dibromo)-2-(4-bromophenyl)diazene unit showed that the eleven closest are those of CSD refcodes TAZDIL (I) [28], HEHKEO (II) [29], ECUDAL (III) [30], PAXDOL (IV) [31], GUPHIL (V) [1, HONBUK (VI) [13], HONBOE (VII) [13], HODQAV (VIII) [20], XIZREG (IX) [14], LEQXOX (X) [19] and LEQXIR (XI) [19].…”

Section: Table 2 Experimental Detailsmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chlorophenyl)-2-(2,2-dibromo-1-(3-nitrophenyl)vinyl)diazene

Akkurt,

Maharramov,

Shikhaliyev

et al. 2023

UNEC j. eng. appl. sci.

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The molecule of the title compound, C14H8Br2ClN3O2, consists of three almost planar groups: the central dibromoethenyldiazene fragment and two attached aromatic rings. The mean planes of these rings form dihedral angles with the plane of the central fragment of 17.00 (13) and 60.91 (13)0 for chlorine- and nitro-substituted rings, respectively. In the crystal, face-to-face π-π stacking interactions connect molecules in zig-zag chains along the a-axis. With halogen⋅⋅⋅halogen, halogen⋅⋅⋅hydrogen, Br⋅⋅⋅H, O⋅⋅⋅H, N⋅⋅⋅H and van der Waals interactions between these chains, molecular packing becomes stable. The most substantial contributions to crystal packing, according to a Hirshfeld surface analysis, are from Br⋅⋅⋅H/H⋅⋅⋅Br (19.6%), H⋅⋅⋅H (12.2%), C⋅⋅⋅H/H⋅⋅⋅C (11.9%) and O⋅⋅⋅H/H⋅⋅⋅O (11.0%) contacts.

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Section: Table 2 Experimental Detailsmentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chlorophenyl)-2-(2,2-dibromo-1-(3-nitrophenyl)vinyl)diazene

Akkurt,

Maharramov,

Shikhaliyev

et al. 2023

UNEC j. eng. appl. sci.

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Crystal structures and Hirshfeld surface analyses of (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-phenyldiazene, (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methylphenyl)diazene, (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methoxyphenyl)diazene and (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(3-methylphenyl)diazene

Maharramov,

Shikhaliyev,

Qajar

et al. 2023

Acta Cryst E

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The crystal structures and Hirshfeld surface analyses of four similar azo compounds are reported. (E)-1-[1-(4-tert-Butylphenyl)-2,2-dichloroethenyl]-2-phenyldiazene, C18H18Cl2N2, (I), and (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methylphenyl)diazene, C19H20Cl2N2, (II), crystallize in the monoclinic space group C2/c with Z = 8, and (E)-1-[1-(4-tert-butylphenyl)-2,2-dichloroethenyl]-2-(4-methoxyphenyl)diazene, C19H20Cl2N2O, (III), in the monoclinic space group P21/c with Z = 4. (E)-1-[1-(4-tert-Butylphenyl)-2,2-dichloroethenyl]-2-(3-methylphenyl)diazene, C19H20Cl2N2, (IV), crystallizes in the triclinic space group P\overline{1} with Z = 4 and comprises two molecules (A and B) in the asymmetric unit. In the crystal structures of (I) and (II), molecules are linked by C—H...π and C—Cl...π interactions, forming layers parallel to (\overline{2}02), while molecules of (III) are linked by C—H...O contacts, C—H...π and C—Cl...π interactions forming layers parallel to (\overline{3}02). The stability of the molecular packing is ensured by van der Waals forces between these layers. In the crystal structure of (IV), molecules are linked by C—H...π and C—Cl...π interactions, forming a tri-periodic network.

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Crystal structures and Hirshfeld surface analyses of methyl 4-{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzoate, methyl 4-{2,2-dichloro-1-[(E)-(4-methylphenyl)diazenyl]ethenyl}benzoate and methyl 4-{2,2-dichloro-1-[(E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate

Shikhaliyev,

İbrahimova,

Atakishiyeva

et al. 2024

Acta Cryst E

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The crystal structures and Hirshfeld surface analyses of three similar azo compounds are reported. Methyl 4-{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzoate, C16H12Cl2N2O2, (I), and methyl 4-{2,2-dichloro-1-[(E)-(4-methylphenyl)diazenyl]ethenyl}benzoate, C17H14Cl2N2O2, (II), crystallize in the space group P21/c with Z = 4, and methyl 4-{2,2-dichloro-1-[(E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate, C18H16Cl2N2O2, (III), in the space group P\overline{1} with Z = 2. In the crystal of (I), molecules are linked by C—H...N hydrogen bonds, forming chains with C(6) motifs parallel to the b axis. Short intermolecular Cl...O contacts of 2.8421 (16) Å and weak van der Waals interactions between these chains stabilize the crystal structure. In (II), molecules are linked by C—H...O hydrogen bonds and C—Cl...π interactions, forming layers parallel to (010). Weak van der Waals interactions between these layers consolidate the molecular packing. In (III), molecules are linked by C—H...π and C—Cl...π interactions forming chains parallel to [011]. Furthermore, these chains are connected by C—Cl...π interactions parallel to the a axis, forming (0\overline{1}1) layers. The stability of the molecular packing is ensured by van der Waals forces between these layers.

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Crystal structure and Hirshfeld surface analysis of a new polymorph of (E)-2-(4-bromophenyl)-1-[2,2-dibromo-1-(3-nitrophenyl)ethenyl]diazene

Cited by 3 publications

References 32 publications

Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chlorophenyl)-2-(2,2-dibromo-1-(3-nitrophenyl)vinyl)diazene

Crystal structure and Hirshfeld surface analysis of (E)-1-(4-chlorophenyl)-2-(2,2-dibromo-1-(3-nitrophenyl)vinyl)diazene

Crystal structures and Hirshfeld surface analyses of methyl 4-{2,2-dichloro-1-[(E)-phenyldiazenyl]ethenyl}benzoate, methyl 4-{2,2-dichloro-1-[(E)-(4-methylphenyl)diazenyl]ethenyl}benzoate and methyl 4-{2,2-dichloro-1-[(E)-(3,4-dimethylphenyl)diazenyl]ethenyl}benzoate

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