Abstract
In the title compound, C14H8Cl2FN3O2, the 4-fluorophenyl ring and the nitro-substituted benzene ring form a dihedral angle of 63.29 (8)°. In the crystal, molecules 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...π, C—F...π and N—O...π interactions. 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%) interactions.
Publisher
International Union of Crystallography (IUCr)
Subject
Condensed Matter Physics,General Materials Science,General Chemistry
Cited by
19 articles.
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1. 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;Acta Crystallographica Section E Crystallographic Communications;2024-01-26
2. 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;Acta Crystallographica Section E Crystallographic Communications;2023-06-13
3. Crystal structure and Hirshfeld surface analysis of a new polymorph of (E)-2-(4-bromophenyl)-1-[2,2-dibromo-1-(3-nitrophenyl)ethenyl]diazene;Acta Crystallographica Section E Crystallographic Communications;2022-07-14
4. Crystal structure and Hirshfeld surface analysis of (E)-2-(4-bromophenyl)-1-[2,2-dibromo-1-(4-nitrophenyl)ethenyl]diazene;Acta Crystallographica Section E Crystallographic Communications;2022-06-16
5. Crystal structure and Hirshfeld surface analysis of (E)-1-[2,2-dibromo-1-(4-nitrophenyl)ethenyl]-2-(4-fluorophenyl)diazene;Acta Crystallographica Section E Crystallographic Communications;2022-04-28