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

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 hydrazone mol­ecule in title monohydrate, C14H13N3O4·H2O, is almost coplanar, the dihedral angle between the terminal benzene rings being 3.22 (15)°; the nitro group is coplanar with the benzene ring to which it is bonded [O—N—C—C = −2.8 (4)°]. The hy­droxy group forms an intra­molecular hydrogen bond with the imine N atom, and the conformation about the imine bond [1.305 (3) Å] is E. In the crystal, supra­molecular layers in the (203) plane are connected into a double layer via water–nitro O—H⋯O hydrogen bonds, along with π–π inter­actions [ring centroid–centroid distance = 3.7859 (19) Å].

Partial Text

For background on the influence of substituents upon the supra­molecular structures of hydrazones, see: Glidewell et al. (2004 ▶); Ferguson et al. (2005 ▶); Baddeley et al. (2009 ▶).