Research Article: (2E)-2-[(2-Hy­droxy-4-meth­oxy­phen­yl)(phen­yl)methyl­idene]-N-phenyl­hydrazinecarboxamide dimethyl­formamide monosolvate

Date Published: May 01, 2012

Publisher: International Union of Crystallography

Author(s): C. F. Annie, Jinsa Mary Jacob, M. Sithambaresan, M. R. Prathapachandra Kurup.


The title compound, C21H19N3O3·C3H7NO, adopts an E conformation with respect to the azomethine bond and crystallizes in the amide form. The dihedral angle between the rings lined to the C=N bond is 88.60 (12)°. The dimethyl­formamide solvent mol­ecule is disordered over two orientations with site occupancies of 0.684 (3) and 0.316 (3). The two N atoms of the hydrazinecarboxamide group are involved in inter­molecular N—H⋯O hydrogen bonds in which the dimethyl­formamide O atom acts as acceptor. The structure also features π–π inter­actions, with a centroid–centroid distance of 3.6561 (13) Å. Classical and non-classical intra­molecular O—H⋯N and C—H⋯O hydrogen bonds are also present.

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For applications of hydrazinecarboxamide and its derivatives, see: Afrasiabi et al. (2005 ▶); Alam et al. (2010 ▶). For related structures, see: Siji et al. (2010 ▶); Reena & Kurup (2010 ▶); Sithambaresan & Kurup (2011 ▶). For standard bond-length data, see: March (1992 ▶); Kala et al. (2007 ▶). For the synthesis, see: Sreekanth et al. (2004 ▶).