(±)-4,12,15,18,26-Pentahydroxy-13,17-dioxaheptacyclo[14.10.0.03,14.04,12.06,11.018,26.019,24]hexacosa-1,3(14),6(11),7,9,15,19,21,23-nonaene-5,25-dione monohydrate

The title compound, C24H14O9·H2O, displays a cup-shaped form. The water molecule is disordered over two set of sites with an occupancy ratio of 0.78:0.22. The molecule of the compound has four stereocenters and corresponds to the SSRR/RRSS diastereoisomer. In the molecule, the maximum dihedral angle between the planar benzene rings is 80.40 (4)°. The H atoms of the hydroxy groups are engaged in hydrogen bonding, forming infinite chains parallel to the a axis. These chains are interlinked through water molecules, resulting in the formation of a two-dimensional network parallel to the (001) plane. Futhermore C—H⋯O, C—H⋯π and slipped π–π interactions result in the formation of a three-dimensional network.

The title compound, C 24 H 14 O 9 ÁH 2 O, displays a cup-shaped form. The water molecule is disordered over two set of sites with an occupancy ratio of 0.78:0.22. The molecule of the compound has four stereocenters and corresponds to the SSRR/RRSS diastereoisomer. In the molecule, the maximum dihedral angle between the planar benzene rings is 80.40 (4) . The H atoms of the hydroxy groups are engaged in hydrogen bonding, forming infinite chains parallel to the a axis. These chains are interlinked through water molecules, resulting in the formation of a two-dimensional network parallel to the (001) plane. Futhermore C-HÁ Á ÁO, C-HÁ Á Á and slippedinteractions result in the formation of a three-dimensional network.   Table 1 Hydrogen-bond geometry (Å , ).
The title compound (I) displays a cup shaped form (Fig. 1). In (I), the central group A (C1-C6/C8/C17/O1/O2/O6), the armed groups B (C7/C9/O5/C10-C15) and C (C16/C18/O9/C19-C24) are planar with r. m. s. deviations of 0.0250, 0.0462 and 0.0190 Å, respectively. The adjacent atoms C7 and C16 to central group A are at a distance of 0.3706 (22) and 0.3424 (22) Å, respectively from the mean square plane and thus forming envelop form from two sides. The group B also form envelop shape with C8 at a distance of 0.3203 (23) Å from its mean square plane. The C17 atom is at a distance of -0.1997 (24) Å from the mean square plane of group C. The dihedral angle between A/B, A/C and B/C is 80.40 (4)°, 78.55 (4)° and 38.59 (4)°, respectively. The molecule of (I) has stereo centers at C7, C8, C16 and C17 and corresponds to the SSRR/RRSS diastereoisomer. Intermolecular O-H···O hydrogen bonds involving the hydroxy groups build up infinite one dimensional chain parallel to the a axis (Table 1, Fig. 2) . Hydrogen bonds involving the water molecule link the chains to form a two dimensionnal network parallel to the (0 0 1) plane (Table 1) and weak C-H···O hydrogen bonds (Table 1) connect the sheet to build up a three dimensional network. The packing is further stabilized through C-H···π and slippest π-π interactions (Tables 1 and 2).
The crystal structure of (I) is closeled related to the structure of 4b,7a,12a,13,13b-pentahydroxy-4 b,7a,12a, 13b-tetrahy- The differences with I are due to the bonding around phenol ring and inclusion of methanol solvate instead of water.

Experimental
The pyrogallol (0.10 g, 0.793 mmol) was added to the stirred solution of ninhydrin (0.29 g, 1.586 mmol) in 15 ml of acetic acid at 323 K for 45 min and kept at room temperature for five days in a closed vessel. White colorless prisms for x-ray analysis of the title compound (I) were separated and washed with acetic acid and Petrolium ether.

Refinement
The high values of thermal parameters of the solvent water lead to the disorder. The water molecule is disordered over two set of sites with occupancy ratio of groups is 0.786 (5):0.214 (5). The disordered water molecules were treated with equal thermal parameters. One of the H-atom shares both disordered molecules. supplementary materials sup-2 All H atoms attached to C atoms and O atom of hydroxy groups were fixed geometrically and treated as riding with C-H = 0.93 and O-H = 0.82 Å with U iso (H) = 1.2U eq (C) or U iso (H) = 1.5U eq (O). H atoms of the disordered water molecule were located in difference Fourier maps and included in the subsequent refinement using restraints (O-H = 0.85 (1)Å and H···H = 1.40 (2)Å) with U iso (H) = 1.5U eq (O). In the last cycles of refinement they were treated as riding on their parent O atom. Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 30% probability level. H-atoms are shown by small circles of arbitrary radii. For the sake of clarity, only the major component of the disordered water molecule is represented.

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 > 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.