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

Abstract

The mol­ecule of the title compound, C15H14N4O5, is in an E conformation with respect to the C=N double bond and the dihedral angle between the two benzene rings is 37.83 (7)°. The ethyl­idenehydrazine plane makes dihedral angles of 4.93 (9) and 42.38 (9)° with the two benzene rings. 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 into chains along the c axis which are stacked along the b axis by aromatic π–π inter­actions with a centroid–centroid distance of 3.5927 (10) Å.

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

“…The middle ethylidenehydrazine unit (C7/C14/N1/N2) is planar with an r.m.s deviation of 0.0040 (1) Å and the torsion angle of N2-N1-C7-C14 is -1.3 2 Table 1) generates an S(6) ring motif (Bernstein et al, 1995). The bond distances are within the normal range (Allen et al, 1987) and are comparable with related structures (Fun et al, 2010(Fun et al, , 2011Jansrisewangwong et al, 2010;Nilwanna et al, 2011).…”

“…Hydrazones have been known to be responsible for various bioactivities such as antibacterial (Angelusiu et al, 2010), antioxidant (Li et al, 2008), antifungal (Loncle et al, 2004), anti-inflammatory (Gokce et al, 2009) and also tyrosinase inhibitory (Bendre et al, 1998) activities. With our on-going research on medicinal chemistry, we previously reported the syntheses and crystal structures of some hydrazone derivatives (Fun et al, 2010(Fun et al, , 2011Jansrisewangwong et al, 2010;Nilwanna et al, 2011). Herein we report the crystal structure of the title compound.…”

“…For hydrogenbond motifs, see: Bernstein et al (1995). For related structures, see: Fun et al (2010Fun et al ( , 2011; Jansrisewangwong et al (2010); Nilwanna et al (2011). For background to and the biological activity of hydrozones, see: Angelusiu et al (2010); Bendre et al (1998); Gokce et al (2009); Li et al (2008); Loncle et al (2004).…”

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

“…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).…”