1-Benzoyl-4-(2-nitrophenyl)semicarbazide

The title compound, C14H12N4O4, was prepared by the reaction of 2-nitrophenyl isocyanate with benzoylhydrazine. The dihedral angle between the rings is 71.49 (6)) Å. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond, generating an S(6) ring. The crystal packing shows N—H⋯O hydrogen bonds.

The title compound, C 14 H 12 N 4 O 4 , was prepared by the reaction of 2-nitrophenyl isocyanate with benzoylhydrazine. The dihedral angle between the rings is 71.49 (6)) Å . The molecular conformation is stabilized by an intramolecular N-HÁ Á ÁO hydrogen bond, generating an S(6) ring. The crystal packing shows N-HÁ Á ÁO hydrogen bonds.   Table 1 Hydrogen-bond geometry (Å , ).  For example, aryl urea derivates have been found to inhibit cell division as weedicides, and homologous aryl urea derivates have also been researched as antibacterial activity. Thidiazuron, a substituted heterocyclic urea compound, mimicked the effect of benzyladenine(BA) in the Ca 2+ + cytokinin system and the IAA + cytokinin systems systems. (Yip et al., 1986).

Related literature
Recently, better activity of sectiona benzoyl urea derivates were reported. (Liu et al., 2005). In order to discover further biologically active urea compounds, the title compound was synthesized and its crystal structure was determined ( Fig.   1). The molecular conformation is stabilized by an intramolecular N-H···O hydrogen bond. The crystal packing shows N-H···O hydrogen-bonds. (Fig. 2).
Experimental 2-nitrophenyl isocyanate(0.164 g, 1 mmol) and benzoyl hydrazine (0.136 g, 1 mmol) were milled and mixed thoroughly in an agate mortar. Then the mixture was put into a beaker and irradiated by microwave for 1 min. After the reaction was completed, the resulting mixture was dissolved in 95% ethanol and filtrated. The products separated and were collected by filtration. The title compound was recrystallized from ethanol and single crystals were obtained by slow evaporation.

Refinement
In the absence of anomalous scatterers, the absolute structure could not be determined and, therefore, Friedel pairs were merged. All H atoms bonded to C atoms were placed in calculated positions, with C-H = 0.95 Å, and included in the refinement using a riding model, with U iso (H) = 1.2U eq (C). H atoms bonded to N were freely refined. Fig. 1. The asymmetric unit of the title compound with displacement ellipsoids drawn at the 30% probability level.

Special details
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.