N′-(2-Fluorobenzoyl)benzohydrazide

In the crystal structure of the title compound, C14H11FN2O2, the molecule is centrosymmetric. The F atom is disordered over four positions, on the two ortho positions of each ring, with occupancies of 0.287:0.213 (5). In the crystal structure, molecules are linked by intermolecular N—H⋯O and C—H⋯O hydrogen bonds.


Structure Reports Online
In view of the versatility of these compounds, we have synthesized the title compound, (I), using a literature method (Zareef et al., 2007) and reported its crystal structure. The geometry of (I) is normal and (Table 1) compares well with those found in other crystal structures (Silva et al., 2006;Chopra et al., 2006;Souza et al., 2007). The title molecule, C 14 H 11 N 2 O 2 F, is non-planar. The dihedral angle between the benzene rings and CONHNHCO group is 34.5 (5) °. The disorder of the title molecule is realised by the presents of two positions for F atom with occupancy factors of 0.3 for F10 and 0.2 for F10'.
The molecules are linked into a three-dimensional framework by a combination of two N-H···O and one weak C-H···O hydrogen bonds.

Experimental
For the synthesis of title compound (I), benzoyl chloride (5.1 mmol) was added in portions to a suspension of 2-fluorobenzoic hydrazide (5.0 mmol) in dry acetonitrile (50 ml), and the reaction mixture was stirred for 9 h at 296 K. Then, the resulting mixture was concentrated, and the solid product filtered and recrystallized from aqueous ethanol to afford the title compound (yield; 87%). Suitable crystals were grown from a solution of (I) in ethanol by slow evaporation at room temperature.

Refinement
The occupancy factors for the disordered fluorine and hydrogen (H5 and H9) atoms were refined using free variables. The H5 nad H9 were included in the refinement at geometrically idealized positions with C-H distances 0.96 A and their parameters are not refinement. The remaining H atoms were located in a difference map and freely refined.

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 supplementary materials sup-3 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.
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 > σ(F 2 ) is used only for calculating Rfactors(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.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å 2 )