Received 16 December 2013
The molecule of the title hydrazine derivative, C15H14N4O6, is essentially planar, the dihedral angle between the substituted benzene rings being 2.25 (9)°. The ethoxy and hydroxy groups are almost coplanar with their bound benzene ring [r.m.s. deviation = 0.0153 (2) Å for the ten non-H atoms]. Intramolecular N-HO and O-HOethoxy hydrogen bonds generate S(6) and S(5) ring motifs, respectively. In the crystal, molecules are linked by O-HOnitro hydrogen bonds into chains propagating in . Weak aromatic - interactions, with centroid-centroid distances of 3.8192 (19) and 4.0491 (19) Å, are also observed.
For a related structure and background to hydrazones, see: Fun et al. (2013). For other related structures, see: Fun et al. (2011, 2012). For the measurement of anti-oxidant activity, see: Molyneux (2004).
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, PLATON (Spek, 2009), Mercury (Macrae et al., 2006) and publCIF (Westrip, 2010).
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB7175 ).
The authors thank the Prince of Songkla University for generous support. CSCK thanks the Universiti Sains Malaysia for a postdoctoral research fellowship. The authors extend their appreciation to the Malaysian Government and the Universiti Sains Malaysia for the APEX DE2012 grant No. 1002/PFIZIK/910323.
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