(2,4-Dihydroxy-6-methoxyphenyl)(3,5-dihydroxyphenyl)methanone monohydrate

The title benzophenone compound, C14H12O6·H2O, was isolated from the bark of Garcinia hombroniana Pierre (Guttiferae). The molecule is twisted, the dihedral angle between the two benzene rings being 59.13 (7)°. The methoxy group is approximately coplanar with the attached benzene ring, with a C—O—C—C torsion angle of 1.91 (18)°. The water molecule is disordered over two positions in a 0.555 (19):0.445 (19) ratio. An intramolecular O—H⋯O hydrogen bond generates an S(6) ring motif. The crystal structure is stabilized by intermolecular O—H⋯O hydrogen bonds. These interactions link the molecules into sheets parallel to the ac plane. The sheets are stacked along the b axis by π–π interactions, with centroid–centroid distances of 3.6219 (7) Å. A weak O—H⋯π interaction was also noted.

The crystal is stabilized by intermolecular O-H···O hydrogen bonds. These interactions link the molecules into sheets parallel to the ac plane (Fig. 2). These sheets are stacked along the b axis by π···π interaction with the Cg 1 ···Cg 1 distance of 3.6219 (7) Å (symmetry code 1-x, -y, 1-z) where Cg 1 is the centroid of the C1-C6 benzene ring. A weak O-H···π interaction was also observed (Table 1).
The title compound (I) was isolated from the fraction FEb in the form of shiny yellow crystals by silica gel CC with chloroform-acetone (3:2 v/v) as eluting solvent. The melting point determined was 516-519 K.
supplementary materials sup-2 Refinement Hydroxy H atoms were located from a Fourier difference map and isotropically refined. The C-bound H atoms were placed in calculated positions with d(C-H) = 0.95 Å for aromatic and 0.98 Å for CH 3 atoms. The U iso values were constrained to be 1.5U eq of the carrier atom for O and methyl H atoms, and 1.2U eq for the remaining H atoms. A rotating group model was used for the methyl groups. The water molecule was found to be disordered over two sites in a 0.555 (19): 0.445 (19) occupancy ratio (from refinement). The water-bound H1W1, H2W1, H1WX and H2WX atoms were located from a difference Fourier map and fixed in these positions with U iso (H) = 1.5 U eq (O) Figures   Fig. 1. The molecular structure of the title compound, with 50% probability displacement ellipsoids and the atom-numbering scheme. Open bonds show the minor component of the disordered water molecule. The hydrogen bond is shown as a dashed line. (2,4-Dihydroxy-6-methoxyphenyl)(3,5-dihydroxyphenyl)methanone monohydrate

Special details
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 120.0 (1) K.
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. Atomic displacement parameters (Å 2 )