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].
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 ▶).