Research Article: 2-{(E)-1-[2-(4-Nitro­phen­yl)hydrazin-1-yl­idene]eth­yl}benzene-1,3-diol

Date Published: March 01, 2012

Publisher: International Union of Crystallography

Author(s): R. Alan Howie, James L. Wardell, Solange M. S. V. Wardell, Edward R. T. Tiekink.


The title compound, C14H13N3O4, is close to planar, the dihedral angle between the terminal benzene rings being 5.80 (16)°; the nitro group is coplanar with the benzene ring to which it is bonded [O—N—C—C torsion angle = −177.3 (3)°]. The hy­droxy group forms an intra­molecular hydrogen bond with the imine N atom, and the conformation about the imine bond is E. In the crystal, layers in the (101) plane with an undulating topology are formed by O—H⋯O and N—H⋯O hydrogen bonds along with C—H⋯O inter­actions. Centrosymmetrically related layers are connected via π–π inter­actions [ring centroid–centroid distance = 3.5739 (19) Å] into double layers.

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For background on the influence of substituents upon the supra­molecular structures of hydrazones, see: Glidewell et al. (2004 ▶); Ferguson et al. (2005 ▶); Wardell et al. (2007 ▶); Baddeley, de Souza França et al. (2009 ▶); Baddeley, Howie et al. (2009 ▶); de Souza et al. (2010 ▶); Howie, da Silva Lima et al. (2010 ▶); Howie, de Souza et al. (2010 ▶); Nogueira et al. (2011 ▶); Howie et al. (2011 ▶).