Crystal structures and Hirshfeld surface analyses of the two isotypic compounds (<i>E</i>)-1-(4-bromophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene and (<i>E</i>)-1-(4-chlorophenyl)-2-[2,2-dichloro-1-(4-nitrophenyl)ethenyl]diazene

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The molecule of the title compound, C14H8Br3N3O2, 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 26.35 (15) and 72.57 (14)° for bromine- and nitro-substituted rings, respectively. In the crystal, C—H...Br interactions connect molecules, generating zigzag C(8) chains along the [100] direction. These chains are linked by C—Br...π interactions into layers parallel to (001). van der Waals interactions 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.

Section: Synthesis and Crystallizationmentioning

confidence: 99%

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

Akkurt

Yıldırım

Shikhaliyev

et al. 2022

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“…Seven compounds are closely related to the title compound, viz. CSD refcode GUPHIL (I) (O ¨zkaraca et al, 2020), HONBUK (II) (Akkurt et al, 2019), HONBOE (III) (Akkurt et al, 2019), HODQAV (IV) (Shikhaliyev et al, 2019), XIZREG (V) (Atiog ˘lu et al, 2019), LEQXOX (VI) (Shikhaliyev et al, 2018) and LEQXIR (VII) (Shikhaliyev et al, 2018).…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-dibromo-1-(2-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene

Çelikesir¹,

Akkurt²,

Shikhaliyev³

et al. 2022

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In the title compound, C14H8Br2FN3O2, the nitro-substituted benzene ring and the 4-fluorophenyl ring form a dihedral angle of 65.73 (7)°. In the crystal, molecules 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 interactions and π–π stacking interactions, 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.

“…The title compound was synthesized according to a reported method (Akkurt et al, 2019;Atiog ˘lu et al, 2019;Maharramov et al, 2018;O ¨zkaraca et al, 2020;Shikhaliyev et al, 2018aShikhaliyev et al, ,b, 2019a. A 20 ml screw-neck vial was charged with dimethyl sulfoxide (10 ml), (E)-1-(4-fluorophenyl)-2-(4-nitrobenzylidene)hydrazine…”

Section: Synthesis and Crystallizationmentioning

confidence: 99%

“…(I)(O ¨zkaraca et al, 2020), HONBUK (II)(Akkurt et al, 2019), HONBOE (III)(Akkurt et al, 2019), HODQAV (IV)(Shikhaliyev et al, 2019a), XIZREG (V) (Atiog ˘lu et al, 2019), LEQXOX (VI)(Shikhaliyev et al, 2018a), LEQXIR (VII)(Shikhaliyev et al, 2018b) and PAXDOL (VIII)(C ¸elikesir et al., 2022).…”

mentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-dibromo-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene

Atioğlu¹,

Akkurt²,

Shikhaliyev³

et al. 2022

Self Cite

In the title compound, C14H8Br2FN3O2, the 4-fluorophenyl ring and the nitro-substituted phenyl ring form a dihedral angle of 64.37 (10)°. Molecules 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 interactions, as well as by π–π stacking interactions. 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.