(<i>E</i>)-1-(2,4-Dinitrophenyl)-2-[1-(3-fluorophenyl)ethylidene]hydrazine

Chantrapromma, Suchada; Nilwanna, Boonlerd; Kobkeatthawin, Thawanrat; Jansrisewangwong, Patcharaporn; Fun, Hoong‐Kun

doi:10.1107/s160053681201937x

Cited by 3 publications

(3 citation statements)

References 11 publications

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“…1 and Table 1) generate two S(6) ring motifs (Bernstein et al, 1995). The bond distances are in normal ranges (Allen et al, 1987) and are comparable with the related structures (Chantrapromma et al, 2012;Fun et al, 2010;Nilwanna et al, 2011).…”

Section: Methodssupporting

confidence: 69%

“…Hydrazones are important compounds which have considerable interesting applications involving biological activities such as antibacterial (El-Sherif et al, 2009), antioxidant (Sathyadevi et al, 2012), anticancer (Xia et al, 2008), antiinflammatory (Gokce et al, 2009) and tyrosinase inhibitory (Bendre et al, 1998) activities. With our on-going research on crystal structures, bioactivity and antioxidant activity of hydrazones (Chantrapromma et al, 2012;Fun et al, 2010;Nilwanna et al, 2011), the title compound (I) was synthesized. The evaluation of its antioxidant activity by DPPH scavenging (Molyneux, 2004) was found to be inactive.…”

Section: Methodsmentioning

confidence: 99%

“…For hydrogenbond motifs, see: Bernstein et al (1995). For related structures, see: Chantrapromma et al (2012); Fun et al (2010); Nilwanna et al (2011). For background to the biological activity of hydrozones, see: Bendre et al (1998); El-Sherif (2009); Gokce et al (2009); Molyneux (2004); Sathyadevi et al (2012); Xia et al (2008).…”

Section: Related Literaturementioning

confidence: 99%

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(E)-1-(2,4-Dinitrophenyl)-2-[1-(3-methoxyphenyl)ethylidene]hydrazine

Fun¹,

Chantrapromma²,

Nilwanna³

et al. 2012

Acta Cryst E

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There are two crystallographically independent molecules in the asymmetric unit of the title compound, C15H14N4O5, with different conformations for the methoxy groups. The molecules are both slightly twisted, the dihedral angles between two benzene rings being 8.37 (18)° in one and 7.31 (18)° in the other. In both molecules, the two nitro groups are essentially coplanar with their bound benzene ring, with the r.m.s. deviation of the dinitrobenzene plane being 0.0310 (3) Å in one molecule and 0.0650 (3) Å in the other. In each molecule, an intramolecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, molecules are linked by weak C—H⋯O interactions and stacked along the a axis through π–π interactions, with centroid–centroid distances of 3.651 (2) and 3.721 (2) Å. The crystal studied was a non-merohedral twin with a refined minor component of 20.1 (3)%.

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Section: Methodssupporting

confidence: 69%

Section: Methodsmentioning

confidence: 99%

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(E)-1-(2,4-Dinitrophenyl)-2-[1-(3-methoxyphenyl)ethylidene]hydrazine

Fun¹,

Chantrapromma²,

Nilwanna³

et al. 2012

Acta Cryst E

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Crystal structure and Hirshfeld surface analysis of (E)-1-(2,6-dichlorophenyl)-2-(2-nitrobenzylidene)hydrazine

et al. 2020

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In the title compound, C13H9Cl2N3O2, the 2,6-dichlorophenyl ring and the nitro-substituted benzene ring form a dihedral angle of 21.16 (14)°. In the crystal, face-to-face π–π stacking interactions occur along the a-axis direction between the centroids of the 2,6-dichlorophenyl ring and the nitro-substituted benzene ring. Furthermore, these molecules show intramolecular N—H...Cl and C—H...O contacts and are linked by intermolecular N—H...O and C—H...Cl hydrogen bonds, forming pairs of hydrogen-bonded molecular layers parallel to (20\overline{2}). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (23.0%), O...H/H...O (20.1%), Cl...H/H...Cl (19.0%), C...C (11.2%) and H...C/C...H (8.0%) interactions.

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(E)-1-(2,6-Dichlorophenyl)-2-(3-nitrobenzylidene)hydrazine: crystal structure and Hirshfeld surface analysis

et al. 2020

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The stabilized conformation of the title compound, C13H9Cl2N3O2, is similar to that of the isomeric compound (E)-1-(2,6-dichlorophenyl)-2-(2-nitrobenzylidene)hydrazine. The 2,6-dichlorophenyl ring and the nitro-substituted benzene ring form a dihedral angle of 26.25 (16)°. In the crystal, face-to-face π-π stacking interactions along the a-axis direction occur between the centroids of the 2,6-dichlorophenyl ring and the nitro-substituted benzene ring. The molecules are further linked by C—H...O contacts and N—H...O and C—H...Cl hydrogen bonds, forming pairs of hydrogen-bonded molecular layers parallel to (100). The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions to the crystal packing are from H...H (22.1%), Cl...H/H...Cl (20.5%), O...H/H...O (19.7%), C...C (11.1%) and C...H/H...C (8.3%) interactions.

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(E)-1-(2,4-Dinitrophenyl)-2-[1-(3-fluorophenyl)ethylidene]hydrazine

Cited by 3 publications

References 11 publications

(E)-1-(2,4-Dinitrophenyl)-2-[1-(3-methoxyphenyl)ethylidene]hydrazine

(E)-1-(2,4-Dinitrophenyl)-2-[1-(3-methoxyphenyl)ethylidene]hydrazine

Crystal structure and Hirshfeld surface analysis of (E)-1-(2,6-dichlorophenyl)-2-(2-nitrobenzylidene)hydrazine

(E)-1-(2,6-Dichlorophenyl)-2-(3-nitrobenzylidene)hydrazine: crystal structure and Hirshfeld surface analysis

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