(E)-1-[1-(2-Chlorophenyl)ethylidene]-2-(2,4-dinitrophenyl)hydrazine

Abstract

The title mol­ecule, C14H11ClN4O4, is in an E configuration and is twisted with the dihedral angle between the two benzene rings being 38.48 (8)°. The ethyl­idenehydrazine plane makes dihedral angles of 6.03 (10) and 44.04 (11)°, respectively, with the dinitro- and chloro-substituted benzene rings. The two nitro groups are essentially coplanar with the bound benzene ring, making dihedral angles of 0.9 (2) and 1.65 (18)°. An intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, mol­ecules are linked by a weak C—H⋯O inter­action into a chain along the c axis. The chains are further stacked along the b axis by a π–π inter­action with a centroid–centroid distance of 3.6088 (10) Å.

(E)-1-[1-(3-Chlorophenyl)ethylidene]-2-(2,4-dinitrophenyl)hydrazine

“…In both molecules, the ortho-nitro group of the 2,4-dinitrophenyl is coplanar with the attached benzene ring with the r.m.s. deviation of 0.0164 (2) Å for the nine non H-atoms (C1-C6/N3/O1/O2), and torsion angles O1-N3-C2-C3 = 176.84 (18)° and O2-N3-C2-C3 = -1.9 (3)°, whereas the para-nitro group is slightly twisted with the torsion angles O3-N4-C4-C5 = 168.8 (2)° and O4-N4-C4-C5 = -11.5 (3)° in molecule A; the corresponding values are 0.0176 (2) Å, -177.77 (18), 3.6 (3), 171.1 (2) and -8.9 4 Table 1) generates S(6) ring motifs (Bernstein et al, 1995) The bond distances agree with the literature values (Allen et al, 1987) and are comparable with the related structures (Chantrapromma et al, 2011;Fun et al, 2011;Nilwanna et al, 2011).…”

“…For related literature on hydrogen-bond motifs, see: Bernstein et al (1995). For related structures, see: Chantrapromma et al (2011); Fun et al (2011Fun et al ( , 2012; Nilwanna et al (2011). For background to biological activities of hydrazones, see: Angelusiu et al (2010); Cui et al (2010); Gokce et al (2009); Khan et al (2007): Loncle et al (2004); Wang et al (2009).…”

“…Hydrazones are known to be bioactive compounds with antibacterial, antifungal, antitumor, anti-inflammatory as well as antioxidant (Angelusiu et al, 2010;Cui et al, 2010;Gokce et al, 2009;Khan et al, 2007;Loncle et al, 2004;Wang et al, 2009) activities. Within our on-going research on the bioactivity of hydrazones, the title compound (I) was synthesized in order to study and compare its biological activity with other related compounds (Chantrapromma et al, 2011;Fun et al, 2011;Nilwanna et al, 2011). Herein we report the synthesis and crystal structure of (I).…”

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

“…For hydrogenbond motifs, see: Bernstein et al (1995). For related structures, see: Chantrapromma et al (2011); Fun et al (2011Fun et al ( , 2012; Nilwanna et al (2011). For background to and the biological activity of hydrozones, see: Cui et al (2010); Gokce et al (2009); Krishnamoorthy et al (2011); Molyneux (2004); Wang et al (2009).…”

(1Z,2E)-N′-{2-Chloro-1-methyl-2-[2-(4-methylphenyl)hydrazin-1-ylidene]ethylidene}-4-methoxybenzohydrazide

“…For related structures and background to the bioactivity of hydrazones, see: Chantrapromma et al (2011); Fun et al (2012); Abdel-Aziz & Mekawey (2009); Abdel-Aziz et al (2010). For reference bond lengths, see: Allen et al (1987).…”