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

Abstract

There are two crystallographically independent mol­ecules in the asymmetric unit of the title compound, C14H11ClN4O4, with the same E conformation about the C=N double bond. The mol­ecules are approximately planar, with a dihedral angle between the benzene rings of 10.24 (12)° in one mol­ecule and 4.73 (12)° in the other. In both mol­ecules, the ortho-nitro groups of the 2,4-dinitro­phenyl units are coplanar to their bound benzene rings, whereas the para-nitro groups are slightly twisted. In each mol­ecule, intra­molecular N—H⋯O hydrogen bonds generate S(6) ring motifs. In the crystal, mol­ecules are linked by weak C—H⋯O inter­actions into sheets parallel to the (-102) plane. These sheets are stacked by π–π inter­actions, with centroid–centroid distances of 3.7008 (14) and 3.7459 (14) Å. A Cl⋯O short contact [3.111 (2) Å] is observed.

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

“…An intramolecular N2-H1N2•••O1 hydrogen bond ( Fig.1 and Table 1) generates an S(6) ring motif (Bernstein et al, 1995). The bond distances are in normal ranges (Allen et al, 1987) and are comparable with the closely related structures (Chantrapromma et al, 2011;Fun et al, 2011Fun et al, , 2012Nilwanna et al, 2011).…”

“…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).…”

6-Bromopyridine-2-carbaldehyde phenylhydrazone

“…The central bridge forms a dihedral angle of 0.8 (2)° with the benzene ring and the bromopyridyl and benzene rings form a dihedral angle of 0.5 (2)°. The bond lengths agree with the literature values (Allen et al, 1987) and are comparable with the related structures (Yu et al, 2005;Fun et al, 2012). In the crystal packing (Fig.…”

“…For bond-length data, see: Allen et al (1987). For related structures, see: Yu et al (2005); Fun et al (2012). For the design of molecular dynamic systems, see: Hirose (2010).…”