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

Abstract

The title compound, C14H11N5O6, was obtained from the condensation reaction of 2,4-dinitro­phenyl­hydrazine and 2-nitro­acetophenone. The mol­ecule displays an E conformation about the C=N double bond and an intra­molecular N—H⋯O hydrogen bond generates an S(6) ring motif. The dihedral angle between the benzene rings is 7.84 (6)°. In the crystal, mol­ecules are linked by C—H⋯O hydrogen bonds and π–π stacking inter­actions [centroid–centroid distance = 3.6447 (8) Å] into a three-dimensional network.

(1E,2E)-1,2-Bis[1-(3-chlorophenyl)ethylidene]hydrazine

“…The molecular structure of (I) is shown in (Allen et al, 1987) and are comparable with the related structures (Chantrapromma et al, 2010;Fun et al, 2010;Jansrisewangwong et al, 2010;Nilwanna et al, 2011).…”

“…For background to the biological activity and fluorescent properties of hydrazones, see: Li et al (2009); Qin et al (2009). For related structures see: Chantrapromma et al (2010); ; Jansrisewangwong et al (2010); Nilwanna et al (2011). For standard bond-length data, see: Allen et al (1987).…”

“…For standard bond-length data, see: Allen et al (1987). Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 Due to the interesting applications of hydrazones with respect to their antibacterial, antiviral and antioxidant (Li et al, 2009) as well as fluorescent properties (Qin et al, 2009), we have synthesized a series of hydrazones in order to study these activities and have reported some of these crystal structures (Chantrapromma et al, 2010;Fun et al, 2010Fun et al, ,2011Jansrisewangwong et al, 2010;Nilwanna et al, 2011). As part of our on-going research on the medicinal chemistry of hydrazones, the title compound (I) was synthesized and its biological activities will be reported elsewhere.…”

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

“…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).…”