Hopeahainol C monohydrate.

In the structure of the title compound, C(28)H(16)O(6)·H(2)O [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 mol-ecule lies about an inversion center with the solvent water mol-ecule 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-hy-droxy-phenyl 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 inter-molecular O-H⋯O hydrogen bonds. These inter-actions link the hopeahainol C mol-ecules into chains along the b axis. Water mol-ecules are located inter-stitially between the hopeahainol C mol-ecules linked by O(water)-H⋯O(hy-droxy) and O(hy-droxy)-H⋯O(water) hydrogen bonds. π-π inter-actions 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 = 466.42

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.068

wR(F 2) = 0.161

S = 1.07

2171 reflections

163 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.27 e Å−3

Δρmin = −0.35 e Å−3

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 ▶).

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

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

Supplementary material file. DOI: 10.1107/S1600536811017053/sj5138Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C28H16O6·H2O	F(000) = 968
Mr = 466.42	Dx = 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

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

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(Fo2) + (0.0792P)2 + 1.9771P] where P = (Fo2 + 2Fc2)/3
2171 reflections	(Δ/σ)max = 0.001
163 parameters	Δρmax = 0.27 e Å−3
0 restraints	Δρmin = −0.35 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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···O3iv	0.82	2.00	2.716 (3)	145

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) ; (ii) ; (iii) .