Crystal structure and computational studies of (3Z)-4-benzoyl-3-[(2,4-dinitrophenyl)hydrazinylidene]-5-phenylfuran-2(3H)-one

The molecular structure of the title molecule was confirmed by theoretical calculations using DFT(B3YLP) methods.

As part of our studies in this area, we have synthesized the title furan-2,3-dione derivative and report here its molecular and crystal structure.
A bifurcated intramolecular N-HÁ Á Á(O,O) hydrogen bond involving both the carbonyl O atom of the furane dione moiety and an O atom of one of nitro groups is present, forming two S(6) motifs ( Fig. 1, Table 1).

Figure 2
The packing of molecules in the title compound in a view along [010].
The optimized parameters such as bond lengths, bond angles and torsion angles are in good agreement with experimental values on basis of the diffraction study. The highest deviations between the two methods relate to the C4-C5 bond length [1.368 (3) Å from diffraction data, 1.4008 Å from DFT calculations] and the N4-C19-C20-C21 torsion angle [178.85 (14) from diffraction data, 179.92 from DFT calculations].
The molecular electrostatic potential is a suitable way to interpret the hydrogen-bonding donor and acceptor sides. Electrophilic and nuclecophilic regions are good descriptors for such interactions in a molecular electrostatic potential surface. Generally, colours are used for this description. Redcoloured regions are related to a negative electrostatic potential and associated with electrophilic characteristics while blue-coloured regions are related to positive electrostatic potentials and associated with nuclecophilic characteristics. In the title molecule, negative regions are mainly located on atoms O4 and O5 with a minimum value of À0.045 a.u. Positive regions are located around atom N1 with a maximum value of 0.037 a.u. These regions are associated with hydrogenbonding donor and acceptor sites. The molecular electrostatic potential surface is shown in Fig. 3.

Refinement details
Crystal data, data collection and structure refinement details are summarized in Table 2. The H atom attached to the hydrazine group was located from a difference Fourier map and was refined freely. All other H atoms were positioned geometrically and allowed to ride on their parent atoms with C-H = 0.93 Å and U iso (H) = 1.2U eq (C). The molecular electrostatic potential surface of the title compound, calculated at the B3LYP/6-31 G+(d) level.  SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012).

(3Z)-4-Benzoyl-3-[(2,4-dinitrophenyl)hydrazinylidene]-5-phenylfuran-2(3H)-one
Crystal data 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.