(Furan-2-yl)(5-hy-droxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone.

In the title compound, C(15)H(14)N(2)O(3), the furan ring is disordered over two positions with a refined site-occupancy ratio of 0.587 (11):0.413 (11). The mean plane of the approximately planar pyrazole ring [maximum deviation = 0.0469 (11) Å] makes dihedral angles of 86.13 (11) and 4.5 (5)° with the phenyl and furan rings, respectively. The dihedral angle between the phenyl ring and the major component of the disordered furan ring is 81.8 (5)°. The mol-ecule shows chirality in one of the carbon atoms but the centrosymmetric space group means the compound is a racemic mixture. In the crystal, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds connect the mol-ecules. The crystal structure is further stabilized by π-π stacking inter-actions with a centroid-centroid distance of 3.8646 (12) Å.

In the title compound, C 15 H 14 N 2 O 3 , the furan ring is disordered over two positions with a refined site-occupancy ratio of 0.587 (11):0.413 (11). The mean plane of the approximately planar pyrazole ring [maximum deviation = 0.0469 (11) Å ] makes dihedral angles of 86.13 (11) and 4.5 (5) with the phenyl and furan rings, respectively. The dihedral angle between the phenyl ring and the major component of the disordered furan ring is 81.8 (5) . The molecule shows chirality in one of the carbon atoms but the centrosymmetric space group means the compound is a racemic mixture. In the crystal, intermolecular O-HÁ Á ÁO and C-HÁ Á ÁO hydrogen bonds connect the molecules. The crystal structure is further stabilized bystacking interactions with a centroidcentroid distance of 3.8646 (12) Å .

Related literature
For standard bond lengths, see: Allen et al. (1987).  Table 1 Hydrogen-bond geometry (Å , ).  In the crystal structure, intermolecular O-H···O and C-H···O hydrogen bonds connect the components of the structure.

Experimental
The title compound was synthesized by adding furan-2-carbohydrazide (2 mmol) to a solution of benzoylacetone (2 mmol) in ethanol (20 ml). The mixture was refluxed with stirring for half an hour. The resultant solution was filtered and the white single crystals suitable for X-ray structure determination were recrystallized from ethanol by slow evaporation of the solvents at room temperature over several days.

Refinement
The H atoms of hydroxy group was located in a difference Fourier map and constraied to refine on the parent atom with U iso (H) = 1.5 U eq (O), see Table 1. The remaining H atoms were positioned geometrically with C-H = 0.93-0.97 Å and included in a riding-model approximation with U iso (H) = 1.2 or 1.5 U eq (C). A rotating group model was used for the methyl group. At first similarity and a series of distant restraints were applied to the furane rings but after refinement convereged, only the similarity restraints were removed.  (Furan-2-yl)(5-hydroxy-3-methyl-5-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone supplementary materials sup-3

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.
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 > 2sigma(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.