N′-[(E)-Furan-2-ylmethylidene]-4-hydroxybenzohydrazide

The title compound, C12H10N2O3, exists in the E conformation. The five-membered ring and the phenyl rings form dihedral angles of 36.73 (10) and 12.22 (10)°, respectively, with the central C(=O)N2C unit. The crystal packing is dominated by strong N—H⋯O and O—H⋯N hydrogen bonds. Together with weaker C—H⋯O interactions, these establish a three-dimensional supramolecular network.

The title compound, C 12 H 10 N 2 O 3 , exists in the E conformation. The five-membered ring and the phenyl rings form dihedral angles of 36.73 (10) and 12.22 (10) , respectively, with the central C( O)N 2 C unit. The crystal packing is dominated by strong N-HÁ Á ÁO and O-HÁ Á ÁN hydrogen bonds. Together with weaker C-HÁ Á ÁO interactions, these establish a three-dimensional supramolecular network.

Comment
Hydrazones and their derivatives show excellent biological activities (Sreeja et al., 2004). The great potential applications of aryl-hydrazones as antineoplastic, antiviral and antiinflammatory agents, hammered on the investigations of their derivatives (Rakha et al., 1996). As a continuous work on hydrazone compounds, a new hydrazone derivative,
The compound crystallizes in orthorhombic space group Pna2 1 . This molecule adopts an E configuration with respect to the C5=N1 bond and it exists in the amido form with a C6=O2 bond length of 1.232 (2) Å which is very close to the reported C=O bond length of similar structure (Datta et al., 2013). The O2 and N1 atoms are in Z configuration with respect to C6-N2 having a torsion angle of 3.7 (3)°. The central C(=O)N 2 C unit has dihedral angles of 36.73 (10) and 12.22 (10)°, respectively with the five-membered ring and the phenyl ring.
There are two classical intermolecular N2-H2′···O2 and O3-H3′···N1 hydrogen bond interactions (Fig. 2) between the neighbouring molecule with D···A distances of 2.9187 (19) and 2.971 (2) Å respectively (Table 1). Two weak C-H···O hydrogen bond interactions (Fig. 3) between the H atoms attached at the C5 & C11 and O2 & O3 atoms of neighbouring molecules with D···A distances of 3.160 (2) and 3.202 (2) Å respectively, also promote the classical hydrogen bond interactions forming a supramolecular three-dimensional-hydrogen bonding network in the lattice. Notwithstanding that there are very weak short ring interactions found in the crystal system, they are not significant to support the network since centroid-centroid distances are above 4 Å. Fig. 4 shows a packing diagram of the title compound viewed along a axis.

Experimental
The title compound was prepared by adapting a reported procedure (Emmanuel et al., 2011). A solution of furan-2carbaldehyde (0.096 g, 1 mmol) in methanol/DMF 2:1 (10 ml) was mixed with a methanol/DMF solution (10 ml) of 4hydroxybenzhydrazide (0.152 g, 1 mmol). The mixture was refluxed for 6 h and then cooled to room temperature. Light orange colored crystals were formed which were recrystallized in methanol/DMF (2:1 v/v). Block shaped crystals, suitable for SXRD studies, were obtained after slow evaporation of the solution in air for a few days.

Refinement
The atoms H2′ and H3′ were located from a difference Fourier map and N2-H2′ and O3-H3′ distances are restrained to 0.88±0.01 and 0.84±0.01 Å respectively. All the other H atoms on C were placed in calculated positions, guided by difference maps, with C-H bond distances 0.93 Å. H atoms were assigned as U iso (H)=1.2Ueq(carrier).

Figure 1
ORTEP view of the title compound drawn with 50% probability displacement ellipsoids for the non-H atoms.   Hydrogen-bonding interactions in the crystal structure of C 12 H 10 N 2 O 3 .

Figure 4
Packing diagram of the compound along the a axis. where P = (F o 2 + 2F c 2 )/3 (Δ/σ) max < 0.001 Δρ max = 0.13 e Å −3 Δρ min = −0.10 e Å −3 Extinction correction: SHELXL97 (Sheldrick, 2008), Fc * =kFc[1+0.001xFc 2 λ 3 /sin(2θ)] -1/4 Extinction coefficient: 0.046 (5) Special details Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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.