2-Amino-N′-phenylbenzohydrazide

In the title compound, C13H13N3O, the NNCO unit forms dihedral angles of 35.8 (1) and 84.0 (1)° with the benzene and phenyl rings, respectively. The dihedral angles between the aromatic rings is 61.2 (1)°. An intramolecular N—H⋯O hydrogen bond occurs. In the crystal, molecules are linked by weak N—H⋯O hydrogen bonds into C(4) chains parallel to the c axis. Neighbouring chains are linked by weak N—H⋯N hydrogen bonds, forming R 4 4(20) rings, and resulting in the formation of a two-dimensional network lying parallel to (010). The packing also features π–π stacking interactions between phenyl rings [centroid–centroid distance = 3.803 (2) Å].


Crystal data
Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: DS2196).

Rodríguez Comment
The 2-amino-N′-phenylbenzohydrazide 2 is a key intermediate to obtain quinazolinones and benzotriazepines derivatives.
The quinazolinone nucleous and its derivatives have been extensively studied because of their wide range of pharmacological activities, including antiviral, antibacterial, antifungal, antimalarial, anticancer, antihypertensive, diuretic, anticonvulsant and anti-inflammatory (Kamal et al., 2010). On the other hand, the benzotriazepinones have been described as efficient enzymatic inhibitors (Filippakopoulos et al., 2012;Spencer et al., 2008). We report herein on the synthesis and crystal structure of the title compound, a member of this important family of compounds. In the title molecule, Fig. 1, the NNCO moiety form a dihedral angle of 35.8 (1)° and 84.0 (1)° with benzene and phenyl rings respectively. The dihedral angles between the aromatic rings is 61.2 (1)°. In the crystal the molecules are packed via π-π stacking interaction [centroid-centroid distance 3.803 (2) Å] and linked by N1-H1···O1(x, -y + 3/2, z + 1/2) weak hydrogen bond to form a C(4) chain running parallel to the c axis, which are linked to neighboring chains by N2-H3···N3(x -1, y, z) weak hydrogen bond to form R 4 4 (20) centrosymmetric rings (Bernstein et al., 1995). One intramolecular N-H···O hydrogen bond is observed too, Fig.2, Table1.

Refinement
The H-atoms could be located in difference Fourier maps. H3A and H3B atoms parameters were freely refined. The remaining H atoms, were positioned geometrically and treated using a riding model with N-H = 0.86 Å, C-H = 0.93 with U iso (H) = k × U eq (N,C), where k = 1.2 for both atoms.

Computing details
Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and publCIF (Westrip, 2010).    Special details Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. Refinement. Refinement of F 2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F 2 , conventional R-factors R are based on F, with F set to zero for negative F 2 . The threshold expression of F 2 > 2σ(F 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.