Hopeahainol C monohydrate

Fun, H.-K.; Sudto, K.; Ge, H.-M.; Tan, R.-X.; Hannongbua, S.; Chantrapromma, S.

doi:10.1107/S1600536811017053

organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages o1392-o1393

doi:10.1107/S1600536811017053

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Hopeahainol C monohydrate

Hoong-Kun Fun,^a ^*‡ Kanokorn Sudto,^b Hui-Ming Ge,^c Ren-Xiang Tan,^c Supa Hannongbua ^b and Suchada Chantrapromma ^d §

^aX-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia, ^bDepartment of Chemistry, Faculty of Science, Kasetsart University, Jatujak, Bangkok 10900, Thailand, ^cInstitute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China, and ^dCrystal Materials Research Unit, Department of Chemistry, Faculty of Science, Prince of Songkla University, Hat-Yai, Songkhla 90112, Thailand
^*Correspondence e-mail: hkfun@usm.my

(Received 28 April 2011; accepted 5 May 2011; online 14 May 2011)

In the structure of the title compound, C₂₈H₁₆O₆·H₂O [systematic name 3,11-bis(4-hydroxyphenyl)-4,12-dioxapentacyclo[8.6.1.1^2,5.0^13,17.0^9,18]octadeca-1(16),2,5(18),6,8,10,13(17),14-octaene-7,15-diol monohydrate], the hopeahainol C molecule lies about an inversion center with the solvent water molecule located on a crystallographic twofold axis. Hopeahainol C is an oligostillbenoid compound and was isolated from the bark of Shorea roxburghii G. Don. The five central fused rings are essentially planar with an r.m.s. deviation of 0.0173 (3) Å. The 4-hydroxyphenyl ring is twisted with respect to this plane, with the dihedral angle between the phenyl ring and the fused-ring system being 41.70 (10)°. The crystal features intermolecular O—H⋯O hydrogen bonds. These interactions link the hopeahainol C molecules into chains along the b axis. Water molecules are located interstitially between the hopeahainol C molecules linked by O(water)—H⋯O(hydroxy) and O(hydroxy)—H⋯O(water) hydrogen bonds. π–π interactions are also observed with centroid–centroid distances of 3.6056 (17) and 3.5622 (17) Å. Short O⋯O contacts [2.703 (2)–2.720 (3) Å] are also present in the crystal.

Related literature

For bond-length data, see: Allen et al. (1987 ). For background to oligostillbenoids and their activities, see: Cai et al. (2003 ); Donnelly et al. (2004 ); Ge et al. (2009 ); Jang & Pezzuto (1999 ); Stivala et al. (2001 ). For details of Dipterocarpaceae plants, see: Gorham (1995 ); Hakim (2002 ); Sotheeswaran & Pasuphaty (1993 ); Symington (1974 ). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986 ).

Experimental

Crystal data

C₂₈H₁₆O₆·H₂O
M_r = 466.42
Monoclinic, C 2/c
a = 21.225 (4) Å
b = 3.8500 (7) Å
c = 25.353 (5) Å
β = 108.933 (4)°
V = 1959.7 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.05 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ) T_min = 0.972, T_max = 0.994
7974 measured reflections
2171 independent reflections
1463 reflections with I > 2σ(I)
R_int = 0.082

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.161
S = 1.07
2171 reflections
163 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1W1⋯O2ⁱ	0.92 (3)	1.83 (3)	2.720 (2)	163 (3)
O3—H3A⋯O1Wⁱⁱ	0.82	1.89	2.703 (2)	169
O2—H2A⋯O3ⁱⁱⁱ	0.82	2.00	2.716 (3)	145
Symmetry codes: (i) $[x, -y+1, z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[x, -y+1, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811017053/sj5138sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811017053/sj5138Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811017053/sj5138Isup3.cml

checkCIF report

Comment top

The genus Shorea is the largest genus of the family Dipterocarpaceae and is mostly distributed in Southeast Asia (Symington, 1974). The Dipterocarpaceous plant has already proved to be a rich source of oligostilbene compounds that are derived from stilbene and resveratrol (3,5,4'-trihydroxystilbene) (Gorham, 1995; Hakim, 2002; Sotheeswaran & Pasuphaty, 1993). It also has been known that resveratrol possesses various biological activities including antioxidant (Cai et al., 2003), anti-cancer, chemo-preventive (Jang & Pezzuto, 1999; Stivala et al., 2001) and anti-inflammatory properties (Donnelly et al., 2004). During the course of our research on searching for novel bioactive compounds from Thai dipeterocarpaceous plants, the title compound (I), known as hopeahainol C, was obtained from Shorea roxburghii G. Don. Hopeahainol C is an oligostilbenoid, which is a highly unsaturated resveratrol dimer, and it possesses potent antioxidant activity (Ge et al., 2009). Herein we report its crystal structure.

The molecule of the title oligostilbenoid (I) (Fig. 1), C₂₈H₁₆O₆.H₂O, is a symmetrical dimer. Its asymmetric unit contains one half-molecule. The complete molecule of hopeahainol C is generated by a crystallographic center of symmetry 1/2-x, 3/2-y, -z whereas the other hydrogen atom of the water molecule is generated by a two-fold rotation axis -x, y, 1/2-z. The five central fused rings are essentially planar with the r.m.s. 0.0173 (3) Å for the eighteen non-hydrogen atoms. The 4-hydroxyphenyl ring is twisted which respect to the five central fused rings with the dihedral angle between the phenyl and the five central fused rings being 41.65 (10)°. The dihedral angle between the phenyl and the attached dihydrofuran (O1/C7–C9/C14) rings is 40.50 (15)°. The two hydroxy groups of the half molecule are co-planar with the attached benzene ring with the torsion angles O3–C4–C5–C6 = -178.1 (2)° and C10–C11–C12–O2 = -179.5 (2)°. The bond distances are of normal values (Allen et al., 1987).

In the crystal packing (Fig. 2), the molecules of hopeahainol C are linked into chains along the b axis by O(hydroxy)—H···O(hydroxy) hydrogen bonds which form between the two hydroxy groups (Table 1). The water molecules are located in the interstitials of hopeahainol C molecules and are linked to the molecules of hopehainol C by two types of hydrogen bond i.e. O(water)—H···O(hydroxy) and O(hydroxy)—H···O(water) hydrogens bond (Table 1). The crystal is consolidated by these O—H···O hydrogen bonds. π–π interaction with Cg₁···Cg₃ distance = 3.6055 (17) Å (symmetry code: x, 1+y, z) and Cg₂···Cg₃ distance = 3.5622 (17) Å (symmetry code: 1/2-x, 5/2-y, -z) were observed where Cg1, Cg2 and Cg3 are the centroids of the O1/C7–C9/C14, C8–C10/C8A–C10A and C9–C14 rings, respectively. In addition O···O short contacts [2.703 (2)-2.720 (3) Å] are also presented in the crystal.

Related literature top

For bond-length data, see: Allen et al. (1987). For background to oligostillbenoids and their activities, see: Cai et al. (2003); Donnelly et al. (2004); Ge et al. (2009); Jang & Pezzuto (1999); Stivala et al. (2001). For details of Dipterocarpaceae plants, see: Gorham (1995); Hakim (2002); Sotheeswaran & Pasuphaty (1993); Symington (1974). For the stability of the temperature controller used in the data collection, see Cosier & Glazer, (1986).

Experimental top

The dried powdered bark of Shorea roxburghii G. Don. (1 kg) which was collected during June-August 2010 from Sam Sung District, Khon Kaen province in the northeastern part of Thailand, was macerated in C₂H₅OH (2.5 L) for 7 days. The slurry was filtered and the ethanolic extract obtained was dried with a rotary evaporator under reduced pressure at 313 K. The dried extract (98 g) was ground, dissolved in CH₃OH, mixed with silica gel (118 g), and then dried in hot air oven at 333 K for one day. The sample was separated by using a wet column chromatographic technique. The column was packed with 1 kg of silica gel (200-300 mesh) and was eluted with gradient mixtures of CHCl₃ and CH₃OH (100:0 to 0:100), to give 8 major fractions (A–H). Fraction G was further isolated using sephadex column chromatography, eluted with 100% CH₃OH. Only the blue methanolic extract could be selectively collected and was pre-concentrated and heated for 5-10 minutes at 313-333 K before being left for 2-3 days at 298 K to allow crystallization of hopeahainol C. Colorless needle-shaped single crystals of the hopeahainol C suitable for X-ray structure determination were obtained from CH₃OH by slow evaporation at room temperature after a few days.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound, with 60% probability displacement ellipsoids and the atom-numbering scheme. Atoms with suffix A were generated by the symmetry code 1/2-x, 3/2-y, -z.
	Fig. 2. The crystal packing of the title compound viewed down the a axis, showing chains running along the b axis. Hydrogen bonds are shown as dashed lines.

3,11-bis(4-hydroxyphenyl)-4,12- dioxapentacyclo[8.6.1.1^2,5.0^13,17.0^9,18]octadeca- 1(16),2,5(18),6,8,10,13 (17),14-octaene-7,15-diol monohydrate top

Crystal data top

C₂₈H₁₆O₆·H₂O	F(000) = 968
M_r = 466.42	D_x = 1.581 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2171 reflections
a = 21.225 (4) Å	θ = 2.0–24.8°
b = 3.8500 (7) Å	µ = 0.11 mm⁻¹
c = 25.353 (5) Å	T = 100 K
β = 108.933 (4)°	Needle, colorless
V = 1959.7 (6) Å³	0.25 × 0.15 × 0.05 mm
Z = 4

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	2171 independent reflections
Radiation source: sealed tube	1463 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.082
ϕ and ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −27→27
T_min = 0.972, T_max = 0.994	k = −4→4
7974 measured reflections	l = −32→32

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ²(F_o²) + (0.0792P)² + 1.9771P] where P = (F_o² + 2F_c²)/3
2171 reflections	(Δ/σ)_max = 0.001
163 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₂₈H₁₆O₆·H₂O	V = 1959.7 (6) Å³
M_r = 466.42	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 21.225 (4) Å	µ = 0.11 mm⁻¹
b = 3.8500 (7) Å	T = 100 K
c = 25.353 (5) Å	0.25 × 0.15 × 0.05 mm
β = 108.933 (4)°

Data collection top

Bruker APEX DUO CCD area-detector diffractometer	2171 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2009)	1463 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.994	R_int = 0.082
7974 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.161	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	Δρ_max = 0.27 e Å⁻³
2171 reflections	Δρ_min = −0.35 e Å⁻³
163 parameters

Special details top

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (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 F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O1W	0.0000	0.5114 (9)	0.2500	0.0199 (7)
H1W1	0.0200 (15)	0.649 (9)	0.2803 (13)	0.036 (10)*
O1	0.10067 (8)	0.6569 (5)	0.01488 (7)	0.0151 (5)
O2	0.08243 (8)	0.1345 (5)	−0.16160 (7)	0.0170 (5)
H2A	0.1076	0.0687	−0.1782	0.026*
O3	0.11424 (8)	1.1827 (5)	0.25471 (7)	0.0193 (5)
H3A	0.0782	1.2799	0.2487	0.029*
C1	0.14502 (11)	0.9053 (7)	0.10634 (10)	0.0136 (6)
C2	0.08471 (11)	1.0602 (8)	0.10499 (10)	0.0156 (6)
H2B	0.0521	1.1031	0.0709	0.019*
C3	0.07334 (12)	1.1499 (7)	0.15414 (10)	0.0155 (6)
H3B	0.0331	1.2504	0.1530	0.019*
C4	0.12224 (12)	1.0890 (8)	0.20487 (10)	0.0156 (6)
C5	0.18124 (12)	0.9313 (8)	0.20726 (10)	0.0165 (6)
H5A	0.2133	0.8855	0.2415	0.020*
C6	0.19264 (12)	0.8408 (8)	0.15796 (10)	0.0152 (6)
H6A	0.2327	0.7357	0.1595	0.018*
C7	0.15626 (11)	0.8033 (7)	0.05476 (10)	0.0136 (6)
C8	0.20988 (11)	0.8046 (8)	0.03621 (10)	0.0130 (6)
C9	0.18721 (11)	0.6449 (7)	−0.01786 (10)	0.0124 (6)
C10	0.22099 (11)	0.5734 (7)	−0.05605 (10)	0.0119 (6)
C11	0.18493 (12)	0.4004 (7)	−0.10467 (10)	0.0150 (6)
H11A	0.2051	0.3459	−0.1312	0.018*
C12	0.11835 (12)	0.3081 (7)	−0.11382 (10)	0.0137 (6)
C13	0.08421 (11)	0.3852 (7)	−0.07681 (10)	0.0140 (6)
H13A	0.0397	0.3262	−0.0838	0.017*
C14	0.12110 (11)	0.5554 (7)	−0.02905 (10)	0.0129 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.0212 (12)	0.026 (2)	0.0148 (13)	0.000	0.0088 (11)	0.000
O1	0.0162 (8)	0.0197 (12)	0.0120 (8)	−0.0010 (8)	0.0081 (7)	−0.0009 (9)
O2	0.0175 (8)	0.0233 (13)	0.0119 (8)	−0.0030 (8)	0.0070 (7)	−0.0049 (9)
O3	0.0252 (9)	0.0244 (13)	0.0129 (9)	0.0047 (9)	0.0128 (7)	0.0005 (9)
C1	0.0164 (11)	0.0117 (16)	0.0152 (12)	−0.0029 (11)	0.0086 (9)	−0.0007 (12)
C2	0.0161 (11)	0.0175 (17)	0.0154 (12)	−0.0018 (11)	0.0079 (9)	0.0004 (12)
C3	0.0158 (11)	0.0165 (17)	0.0180 (12)	−0.0008 (11)	0.0106 (9)	−0.0006 (13)
C4	0.0217 (12)	0.0167 (17)	0.0129 (12)	−0.0037 (11)	0.0117 (10)	−0.0019 (12)
C5	0.0189 (11)	0.0174 (17)	0.0139 (12)	−0.0006 (11)	0.0064 (9)	0.0015 (12)
C6	0.0165 (11)	0.0155 (16)	0.0171 (12)	0.0000 (11)	0.0102 (9)	0.0002 (12)
C7	0.0157 (11)	0.0130 (16)	0.0120 (11)	−0.0012 (11)	0.0044 (9)	−0.0005 (12)
C8	0.0170 (11)	0.0128 (16)	0.0109 (11)	0.0002 (11)	0.0069 (9)	0.0009 (12)
C9	0.0166 (11)	0.0099 (15)	0.0122 (11)	0.0013 (11)	0.0068 (9)	0.0019 (12)
C10	0.0155 (11)	0.0102 (16)	0.0122 (11)	0.0019 (10)	0.0073 (9)	0.0035 (12)
C11	0.0198 (11)	0.0156 (17)	0.0128 (12)	0.0003 (11)	0.0097 (9)	0.0008 (12)
C12	0.0202 (11)	0.0100 (16)	0.0116 (11)	−0.0006 (11)	0.0060 (9)	0.0013 (12)
C13	0.0140 (10)	0.0140 (17)	0.0152 (12)	−0.0010 (11)	0.0065 (9)	0.0015 (12)
C14	0.0178 (11)	0.0114 (16)	0.0130 (12)	0.0010 (11)	0.0099 (9)	0.0017 (12)

Geometric parameters (Å, º) top

O1W—H1W1	0.92 (3)	C5—C6	1.392 (3)
O1—C14	1.377 (3)	C5—H5A	0.9300
O1—C7	1.399 (3)	C6—H6A	0.9300
O2—C12	1.377 (3)	C7—C8	1.365 (3)
O2—H2A	0.8200	C8—C9	1.436 (3)
O3—C4	1.377 (3)	C8—C10ⁱ	1.465 (3)
O3—H3A	0.8200	C9—C14	1.382 (3)
C1—C6	1.392 (3)	C9—C10	1.406 (3)
C1—C2	1.403 (3)	C10—C11	1.392 (3)
C1—C7	1.457 (3)	C10—C8ⁱ	1.465 (3)
C2—C3	1.388 (3)	C11—C12	1.402 (3)
C2—H2B	0.9300	C11—H11A	0.9300
C3—C4	1.386 (4)	C12—C13	1.391 (3)
C3—H3B	0.9300	C13—C14	1.376 (4)
C4—C5	1.375 (3)	C13—H13A	0.9300

C14—O1—C7	106.61 (17)	O1—C7—C1	114.32 (19)
C12—O2—H2A	109.5	C7—C8—C9	105.6 (2)
C4—O3—H3A	109.5	C7—C8—C10ⁱ	137.4 (2)
C6—C1—C2	118.5 (2)	C9—C8—C10ⁱ	116.94 (19)
C6—C1—C7	121.0 (2)	C14—C9—C10	121.3 (2)
C2—C1—C7	120.4 (2)	C14—C9—C8	107.8 (2)
C3—C2—C1	120.5 (2)	C10—C9—C8	130.8 (2)
C3—C2—H2B	119.8	C11—C10—C9	116.5 (2)
C1—C2—H2B	119.8	C11—C10—C8ⁱ	131.2 (2)
C4—C3—C2	119.7 (2)	C9—C10—C8ⁱ	112.2 (2)
C4—C3—H3B	120.2	C10—C11—C12	120.2 (2)
C2—C3—H3B	120.2	C10—C11—H11A	119.9
C5—C4—O3	117.2 (2)	C12—C11—H11A	119.9
C5—C4—C3	120.8 (2)	O2—C12—C13	115.8 (2)
O3—C4—C3	122.0 (2)	O2—C12—C11	120.6 (2)
C4—C5—C6	119.5 (2)	C13—C12—C11	123.5 (2)
C4—C5—H5A	120.3	C14—C13—C12	115.0 (2)
C6—C5—H5A	120.3	C14—C13—H13A	122.5
C1—C6—C5	121.0 (2)	C12—C13—H13A	122.5
C1—C6—H6A	119.5	C13—C14—O1	127.5 (2)
C5—C6—H6A	119.5	C13—C14—C9	123.3 (2)
C8—C7—O1	110.7 (2)	O1—C14—C9	109.2 (2)
C8—C7—C1	134.9 (2)

C6—C1—C2—C3	0.7 (4)	C10ⁱ—C8—C9—C14	−178.9 (2)
C7—C1—C2—C3	178.5 (3)	C7—C8—C9—C10	−179.2 (3)
C1—C2—C3—C4	0.7 (4)	C10ⁱ—C8—C9—C10	2.0 (5)
C2—C3—C4—C5	−1.9 (4)	C14—C9—C10—C11	−1.7 (4)
C2—C3—C4—O3	178.0 (3)	C8—C9—C10—C11	177.4 (3)
O3—C4—C5—C6	−178.1 (2)	C14—C9—C10—C8ⁱ	179.0 (2)
C3—C4—C5—C6	1.8 (4)	C8—C9—C10—C8ⁱ	−1.9 (5)
C2—C1—C6—C5	−0.8 (4)	C9—C10—C11—C12	0.4 (4)
C7—C1—C6—C5	−178.5 (3)	C8ⁱ—C10—C11—C12	179.5 (3)
C4—C5—C6—C1	−0.5 (4)	C10—C11—C12—O2	−179.5 (2)
C14—O1—C7—C8	1.7 (3)	C10—C11—C12—C13	1.2 (4)
C14—O1—C7—C1	−176.0 (2)	O2—C12—C13—C14	179.3 (2)
C6—C1—C7—C8	−39.1 (5)	C11—C12—C13—C14	−1.3 (4)
C2—C1—C7—C8	143.2 (3)	C12—C13—C14—O1	−178.7 (3)
C6—C1—C7—O1	138.0 (3)	C12—C13—C14—C9	−0.1 (4)
C2—C1—C7—O1	−39.8 (4)	C7—O1—C14—C13	177.0 (3)
O1—C7—C8—C9	−1.0 (3)	C7—O1—C14—C9	−1.7 (3)
C1—C7—C8—C9	176.1 (3)	C10—C9—C14—C13	1.6 (4)
O1—C7—C8—C10ⁱ	177.4 (3)	C8—C9—C14—C13	−177.7 (3)
C1—C7—C8—C10ⁱ	−5.5 (6)	C10—C9—C14—O1	−179.6 (2)
C7—C8—C9—C14	−0.1 (3)	C8—C9—C14—O1	1.1 (3)

Symmetry code: (i) −x+1/2, −y+3/2, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2ⁱⁱ	0.92 (3)	1.83 (3)	2.720 (2)	163 (3)
O3—H3A···O1Wⁱⁱⁱ	0.82	1.89	2.703 (2)	169
O2—H2A···O3^iv	0.82	2.00	2.716 (3)	145

Symmetry codes: (ii) x, −y+1, z+1/2; (iii) x, y+1, z; (iv) x, −y+1, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₈H₁₆O₆·H₂O
M_r	466.42
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	21.225 (4), 3.8500 (7), 25.353 (5)
β (°)	108.933 (4)
V (Å³)	1959.7 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.25 × 0.15 × 0.05

Data collection
Diffractometer	Bruker APEX DUO CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2009)
T_min, T_max	0.972, 0.994
No. of measured, independent and observed [I > 2σ(I)] reflections	7974, 2171, 1463
R_int	0.082
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.161, 1.07
No. of reflections	2171
No. of parameters	163
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.35

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2ⁱ	0.92 (3)	1.83 (3)	2.720 (2)	163 (3)
O3—H3A···O1Wⁱⁱ	0.82	1.89	2.703 (2)	169
O2—H2A···O3ⁱⁱⁱ	0.82	2.00	2.716 (3)	145

Symmetry codes: (i) x, −y+1, z+1/2; (ii) x, y+1, z; (iii) x, −y+1, z−1/2.

Footnotes

‡Thomson Reuters ResearcherID: A-3561-2009.

§Additional correspondence author, e-mail: suchada.c@psu.ac.th. Thomson Reuters ResearcherID: A-5085-2009.

Acknowledgements

This project was supported by the Thailand Research Fund (grant Nos. DBG5280018 and RTA5380010). The authors are also very grateful to Associate Professor Srunya Vajrodaya, Head of Department of Botany, Faculty of Science, Kasetsart University, Thailand, for identification of the plant specimens. The authors also thank the Malaysian government and Universiti Sains Malaysia for the Research University Grant No. 1001/PFIZIK/811160.

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