Racemic 2'-hydroxy-4',4'-dimethylpyran-1,5-dihydroxyxanthone monohydrate.

THE TITLE XANTHONE (SYSTEMATIC NAME: 3,6,11-trihy-droxy-1,1-dimethyl-2,3-di-hydro-chromeno[2,3-f]chromen-7-one monohydrate), known as pruniflorone N, crystallized as a monohydrate, C18H16O6·H2O. The three ring systems of the xanthone skeleton are approximately coplanar, with an r.m.s. deviation of 0.0270 (1) Å from the plane through the 14 non-H atoms. The O atoms of the two hy-droxy substituents on the benzene rings also lie close to this plane, with deviations of 0.019 (1) and 0.070 (1) Å. The 2'-hy-droxy-4',4'-di-methyl-pyran ring is disordered over two positions with a 0.798 (3):0.202 (3) site-occupancy ratio. An intra-molecular O-H⋯O hydrogen bond generates an S(6) ring motif. In the crystal, the xanthone and water mol-ecules are linked into a three-dimensional network by O-H⋯O hydrogen bonds and weak C-H⋯O inter-actions. π-π inter-actions, with centroid-centroid distances of 3.5982 (7), 3.6081 (7) and 3.6456 (7) Å, are also observed.

Related literature

For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For ring conformations, see: Cremer & Pople (1975 ▶). For bond-length data, see: Allen et al. (1987 ▶). For background to xanthones and their biological activity, see: Boonnak, Karalai et al. (2010 ▶); Boonnak, Khamthip et al. (2010 ▶); Gopal­a­krishnan et al. (1997 ▶); Ho et al. (2002 ▶); Obolskiy et al. (2009 ▶). For related structures, see: Boonnak et al. (2006 ▶); Boonnak, Chantrapromma et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer, (1986 ▶).

Experimental

Crystal data

C18H16O6·H2O

M = 346.20

Orthorhombic,

a = 9.8965 (2) Å

b = 15.2329 (3) Å

c = 20.1122 (4) Å

V = 3031.96 (10) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 100 K

0.65 × 0.21 × 0.13 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.927, T max = 0.985

40070 measured reflections

4949 independent reflections

4378 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.145

S = 1.04

4949 reflections

275 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.71 e Å−3

Δρmin = −0.97 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, PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813021223/sj5348sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813021223/sj5348Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813021223/sj5348Isup3.cml

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

C18H16O6·H2O	Dx = 1.517 Mg m−3
Mr = 346.20	Melting point = 523–525 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4949 reflections
a = 9.8965 (2) Å	θ = 2.0–31.3°
b = 15.2329 (3) Å	µ = 0.12 mm−1
c = 20.1122 (4) Å	T = 100 K
V = 3031.96 (10) Å3	Block, yellow
Z = 8	0.65 × 0.21 × 0.13 mm
F(000) = 1456

Bruker APEXII CCD area-detector diffractometer	4949 independent reflections
Radiation source: sealed tube	4378 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 31.3°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −10→14
Tmin = 0.927, Tmax = 0.985	k = −22→22
40070 measured reflections	l = −27→29

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0754P)2 + 2.1985P] where P = (Fo2 + 2Fc2)/3
4949 reflections	(Δ/σ)max = 0.001
275 parameters	Δρmax = 0.71 e Å−3
0 restraints	Δρmin = −0.97 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 e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	Occ. (<1)
O1	0.58520 (10)	1.15586 (6)	0.38580 (5)	0.01809 (19)
O2	0.40787 (9)	1.05055 (6)	0.32849 (4)	0.01448 (18)
O3	0.36164 (10)	1.03467 (6)	0.12623 (5)	0.0205 (2)
O4	0.17901 (10)	0.92011 (7)	0.14256 (5)	0.0201 (2)
O5A	0.03637 (14)	0.85070 (10)	0.35563 (7)	0.0161 (3)	0.798 (3)
O6A	0.12745 (13)	0.76392 (8)	0.43976 (6)	0.0202 (3)	0.798 (3)
H6A	0.082 (3)	0.7235 (18)	0.4244 (13)	0.031 (7)*	0.798 (3)
O5B	0.0688 (6)	0.8401 (5)	0.3682 (3)	0.0161 (3)	0.202 (3)
O6B	0.0235 (10)	0.7824 (7)	0.4712 (4)	0.072 (3)	0.202 (3)
H6B	0.0048	0.7334	0.4570	0.108*	0.202 (3)
C1	0.48453 (11)	1.10150 (7)	0.28720 (6)	0.0129 (2)
C2	0.57959 (12)	1.15648 (8)	0.31807 (6)	0.0144 (2)
C3	0.66177 (12)	1.20850 (8)	0.27862 (6)	0.0163 (2)
H3A	0.7261	1.2444	0.2985	0.020*
C4	0.64937 (13)	1.20774 (8)	0.20928 (6)	0.0179 (2)
H4A	0.7054	1.2430	0.1835	0.021*
C5	0.55441 (13)	1.15485 (8)	0.17905 (6)	0.0170 (2)
H5A	0.5450	1.1553	0.1330	0.020*
C6	0.47209 (12)	1.10035 (8)	0.21811 (6)	0.0140 (2)
C7	0.37462 (12)	1.04051 (8)	0.18811 (6)	0.0148 (2)
C8	0.29411 (12)	0.98915 (7)	0.23357 (6)	0.0135 (2)
C9	0.19417 (12)	0.93068 (8)	0.20908 (6)	0.0148 (2)
C10	0.11267 (12)	0.88544 (8)	0.25236 (6)	0.0165 (2)
H10A	0.0455	0.8483	0.2364	0.020*
C11	0.13192 (13)	0.89594 (8)	0.32090 (6)	0.0164 (2)
C14	0.25267 (13)	0.95266 (8)	0.42430 (6)	0.0174 (2)
C15	0.23195 (12)	0.94999 (8)	0.34905 (6)	0.0142 (2)
C16	0.31063 (11)	0.99645 (7)	0.30282 (6)	0.0125 (2)
C12A	0.05298 (16)	0.84187 (10)	0.42636 (8)	0.0164 (3)	0.798 (3)
H12A	−0.0370	0.8351	0.4461	0.020*	0.798 (3)
C13A	0.11699 (19)	0.92194 (15)	0.45651 (13)	0.0174 (4)	0.798 (3)
H13A	0.1332	0.9104	0.5033	0.021*	0.798 (3)
H13B	0.0528	0.9700	0.4538	0.021*	0.798 (3)
C18A	0.36942 (19)	0.89084 (13)	0.44175 (10)	0.0194 (4)	0.798 (3)
H18A	0.3486	0.8326	0.4266	0.029*	0.798 (3)
H18B	0.3823	0.8902	0.4891	0.029*	0.798 (3)
H18C	0.4506	0.9109	0.4205	0.029*	0.798 (3)
C19A	0.28024 (18)	1.04439 (18)	0.45227 (13)	0.0197 (4)	0.798 (3)
H19A	0.2176	1.0855	0.4333	0.030*	0.798 (3)
H19B	0.3709	1.0617	0.4414	0.030*	0.798 (3)
H19C	0.2695	1.0436	0.4997	0.030*	0.798 (3)
C12B	0.1244 (7)	0.8194 (4)	0.4320 (3)	0.0164 (3)	0.202 (3)
H12B	0.2063	0.7834	0.4295	0.020*	0.202 (3)
C13B	0.1485 (10)	0.9088 (8)	0.4616 (6)	0.0174 (4)	0.202 (3)
H13C	0.0658	0.9430	0.4602	0.021*	0.202 (3)
H13D	0.1759	0.9031	0.5077	0.021*	0.202 (3)
C18B	0.3963 (9)	0.9160 (6)	0.4462 (5)	0.0194 (4)	0.202 (3)
H18D	0.4651	0.9575	0.4342	0.029*	0.202 (3)
H18E	0.4132	0.8612	0.4241	0.029*	0.202 (3)
H18F	0.3975	0.9072	0.4934	0.029*	0.202 (3)
C19B	0.2419 (10)	1.0488 (9)	0.4550 (7)	0.0197 (4)	0.202 (3)
H19D	0.1551	1.0733	0.4446	0.030*	0.202 (3)
H19E	0.3115	1.0852	0.4365	0.030*	0.202 (3)
H19F	0.2526	1.0458	0.5024	0.030*	0.202 (3)
O1W	0.28541 (14)	0.24213 (8)	0.57159 (6)	0.0341 (3)
H1O4	0.239 (3)	0.9598 (17)	0.1248 (14)	0.057 (8)*
H1O1	0.654 (2)	1.1869 (15)	0.3967 (11)	0.037 (6)*
H2W1	0.307 (2)	0.1986 (15)	0.5874 (11)	0.032 (5)*
H1W1	0.316 (3)	0.2464 (17)	0.5304 (14)	0.053 (7)*

	U11	U22	U33	U12	U13	U23
O1	0.0202 (4)	0.0208 (4)	0.0132 (4)	−0.0044 (3)	−0.0025 (3)	−0.0005 (3)
O2	0.0139 (4)	0.0180 (4)	0.0115 (4)	−0.0039 (3)	−0.0002 (3)	0.0012 (3)
O3	0.0252 (5)	0.0249 (5)	0.0114 (4)	−0.0025 (4)	−0.0014 (3)	−0.0001 (3)
O4	0.0225 (5)	0.0230 (4)	0.0148 (4)	−0.0026 (4)	−0.0040 (3)	−0.0032 (3)
O5A	0.0150 (7)	0.0206 (6)	0.0127 (7)	−0.0041 (5)	−0.0042 (4)	0.0038 (4)
O6A	0.0239 (6)	0.0134 (5)	0.0232 (6)	−0.0028 (4)	−0.0061 (5)	0.0020 (4)
O5B	0.0150 (7)	0.0206 (6)	0.0127 (7)	−0.0041 (5)	−0.0042 (4)	0.0038 (4)
O6B	0.067 (6)	0.103 (7)	0.046 (4)	−0.054 (5)	−0.018 (4)	0.041 (5)
C1	0.0124 (5)	0.0137 (5)	0.0128 (5)	0.0005 (4)	0.0012 (4)	0.0012 (4)
C2	0.0142 (5)	0.0139 (5)	0.0151 (5)	0.0014 (4)	−0.0001 (4)	−0.0005 (4)
C3	0.0158 (5)	0.0139 (5)	0.0191 (5)	−0.0016 (4)	0.0007 (4)	0.0000 (4)
C4	0.0189 (5)	0.0166 (5)	0.0181 (5)	−0.0014 (4)	0.0043 (4)	0.0026 (4)
C5	0.0187 (5)	0.0175 (5)	0.0147 (5)	0.0005 (4)	0.0026 (4)	0.0017 (4)
C6	0.0143 (5)	0.0150 (5)	0.0126 (5)	0.0009 (4)	0.0007 (4)	0.0005 (4)
C7	0.0155 (5)	0.0157 (5)	0.0132 (5)	0.0020 (4)	−0.0004 (4)	0.0001 (4)
C8	0.0131 (5)	0.0145 (5)	0.0127 (5)	0.0010 (4)	−0.0008 (4)	−0.0004 (4)
C9	0.0148 (5)	0.0148 (5)	0.0149 (5)	0.0024 (4)	−0.0026 (4)	−0.0022 (4)
C10	0.0147 (5)	0.0148 (5)	0.0201 (6)	−0.0007 (4)	−0.0005 (4)	−0.0033 (4)
C11	0.0167 (5)	0.0134 (5)	0.0191 (6)	−0.0004 (4)	0.0034 (4)	−0.0008 (4)
C14	0.0193 (5)	0.0190 (5)	0.0137 (5)	0.0008 (4)	0.0034 (4)	0.0033 (4)
C15	0.0151 (5)	0.0130 (5)	0.0145 (5)	0.0009 (4)	0.0017 (4)	0.0002 (4)
C16	0.0116 (5)	0.0125 (4)	0.0133 (5)	0.0005 (4)	−0.0007 (4)	0.0001 (4)
C12A	0.0149 (6)	0.0202 (7)	0.0142 (6)	−0.0004 (5)	0.0013 (5)	0.0024 (5)
C13A	0.0145 (11)	0.0199 (9)	0.0178 (7)	0.0005 (7)	0.0024 (8)	−0.0019 (6)
C18A	0.0179 (9)	0.0230 (10)	0.0172 (7)	−0.0029 (6)	−0.0011 (6)	0.0038 (7)
C19A	0.0226 (11)	0.0229 (7)	0.0137 (6)	−0.0067 (11)	0.0018 (10)	−0.0021 (5)
C12B	0.0149 (6)	0.0202 (7)	0.0142 (6)	−0.0004 (5)	0.0013 (5)	0.0024 (5)
C13B	0.0145 (11)	0.0199 (9)	0.0178 (7)	0.0005 (7)	0.0024 (8)	−0.0019 (6)
C18B	0.0179 (9)	0.0230 (10)	0.0172 (7)	−0.0029 (6)	−0.0011 (6)	0.0038 (7)
C19B	0.0226 (11)	0.0229 (7)	0.0137 (6)	−0.0067 (11)	0.0018 (10)	−0.0021 (5)
O1W	0.0452 (7)	0.0290 (6)	0.0280 (6)	0.0157 (5)	0.0178 (5)	0.0078 (5)

O1—C2	1.3635 (15)	C11—C15	1.4065 (17)
O1—H1O1	0.86 (2)	C14—C13B	1.439 (12)
O2—C1	1.3665 (14)	C14—C15	1.5279 (17)
O2—C16	1.3681 (14)	C14—C19A	1.531 (3)
O3—C7	1.2543 (15)	C14—C18A	1.531 (2)
O4—C9	1.3557 (15)	C14—C13A	1.563 (3)
O4—H1O4	0.92 (3)	C14—C18B	1.589 (10)
O5A—C11	1.3627 (18)	C14—C19B	1.593 (14)
O5A—C12A	1.4383 (19)	C15—C16	1.4041 (16)
O6A—C12A	1.4233 (19)	C12A—C13A	1.502 (3)
O6A—H6A	0.82 (3)	C12A—H12A	0.9800
O5B—C11	1.421 (7)	C13A—H13A	0.9700
O5B—C12B	1.432 (8)	C13A—H13B	0.9700
O6B—C12B	1.391 (10)	C18A—H18A	0.9600
O6B—H6B	0.8200	C18A—H18B	0.9600
C1—C6	1.3951 (15)	C18A—H18C	0.9600
C1—C2	1.4043 (16)	C19A—H19A	0.9600
C2—C3	1.3852 (16)	C19A—H19B	0.9600
C3—C4	1.4001 (17)	C19A—H19C	0.9600
C3—H3A	0.9300	C12B—C13B	1.506 (14)
C4—C5	1.3791 (18)	C12B—H12B	0.9800
C4—H4A	0.9300	C13B—H13C	0.9700
C5—C6	1.4037 (16)	C13B—H13D	0.9700
C5—H5A	0.9300	C18B—H18D	0.9600
C6—C7	1.4579 (17)	C18B—H18E	0.9600
C7—C8	1.4432 (16)	C18B—H18F	0.9600
C8—C16	1.4068 (16)	C19B—H19D	0.9600
C8—C9	1.4192 (16)	C19B—H19E	0.9600
C9—C10	1.3723 (17)	C19B—H19F	0.9600
C10—C11	1.4007 (17)	O1W—H2W1	0.76 (2)
C10—H10A	0.9300	O1W—H1W1	0.88 (3)
C2—O1—H1O1	106.5 (15)	C15—C14—C19B	113.5 (5)
C1—O2—C16	120.22 (9)	C18A—C14—C19B	121.8 (4)
C9—O4—H1O4	103.5 (17)	C13A—C14—C19B	93.3 (4)
C11—O5A—C12A	118.35 (12)	C18B—C14—C19B	106.0 (5)
C12A—O6A—H6A	105.8 (19)	C16—C15—C11	114.76 (11)
C11—O5B—C12B	124.3 (5)	C16—C15—C14	124.61 (11)
C12B—O6B—H6A	65.6 (13)	C11—C15—C14	120.58 (11)
C12B—O6B—H6B	109.5	O2—C16—C15	116.35 (10)
O2—C1—C6	123.31 (10)	O2—C16—C8	120.19 (10)
O2—C1—C2	116.24 (10)	C15—C16—C8	123.45 (11)
C6—C1—C2	120.46 (11)	O6A—C12A—O5A	108.92 (13)
O1—C2—C3	123.52 (11)	O6A—C12A—C13A	112.50 (13)
O1—C2—C1	117.70 (10)	O5A—C12A—C13A	111.81 (15)
C3—C2—C1	118.78 (11)	O6A—C12A—H12A	107.8
C2—C3—C4	120.95 (11)	O5A—C12A—H12A	107.8
C2—C3—H3A	119.5	C13A—C12A—H12A	107.8
C4—C3—H3A	119.5	C12A—C13A—C14	115.99 (17)
C5—C4—C3	120.25 (11)	C12A—C13A—H13A	108.3
C5—C4—H4A	119.9	C14—C13A—H13A	108.3
C3—C4—H4A	119.9	C12A—C13A—H13B	108.3
C4—C5—C6	119.62 (11)	C14—C13A—H13B	108.3
C4—C5—H5A	120.2	H13A—C13A—H13B	107.4
C6—C5—H5A	120.2	C14—C18A—H18A	109.5
C1—C6—C5	119.93 (11)	C14—C18A—H18B	109.5
C1—C6—C7	118.58 (11)	C14—C18A—H18C	109.5
C5—C6—C7	121.48 (11)	C14—C19A—H19A	109.5
O3—C7—C8	122.25 (11)	C14—C19A—H19B	109.5
O3—C7—C6	121.51 (11)	C14—C19A—H19C	109.5
C8—C7—C6	116.23 (10)	O6B—C12B—O5B	108.8 (6)
C16—C8—C9	118.31 (11)	O6B—C12B—C13B	104.9 (8)
C16—C8—C7	121.35 (10)	O5B—C12B—C13B	102.5 (7)
C9—C8—C7	120.33 (10)	O6B—C12B—H6A	58.2 (11)
O4—C9—C10	120.09 (11)	O5B—C12B—H6A	90.9 (11)
O4—C9—C8	119.61 (11)	C13B—C12B—H6A	161.6 (12)
C10—C9—C8	120.30 (11)	O6B—C12B—H12B	113.3
C9—C10—C11	119.15 (11)	O5B—C12B—H12B	113.3
C9—C10—H10A	120.4	C13B—C12B—H12B	113.3
C11—C10—H10A	120.4	H6A—C12B—H12B	71.7
O5A—C11—C10	110.63 (11)	C14—C13B—C12B	109.1 (8)
O5A—C11—C15	125.32 (12)	C14—C13B—H13C	109.9
C10—C11—C15	123.96 (11)	C12B—C13B—H13C	109.9
C10—C11—O5B	122.0 (3)	C14—C13B—H13D	109.9
C15—C11—O5B	113.0 (3)	C12B—C13B—H13D	109.9
C13B—C14—C15	114.1 (5)	H13C—C13B—H13D	108.3
C13B—C14—C19A	111.1 (5)	C14—C18B—H18D	109.5
C15—C14—C19A	114.34 (14)	C14—C18B—H18E	109.5
C13B—C14—C18A	97.8 (4)	H18D—C18B—H18E	109.5
C15—C14—C18A	108.17 (12)	C14—C18B—H18F	109.5
C19A—C14—C18A	110.04 (14)	H18D—C18B—H18F	109.5
C15—C14—C13A	106.70 (13)	H18E—C18B—H18F	109.5
C19A—C14—C13A	105.91 (13)	C14—C19B—H19D	109.5
C18A—C14—C13A	111.67 (12)	C14—C19B—H19E	109.5
C13B—C14—C18B	109.5 (5)	H19D—C19B—H19E	109.5
C15—C14—C18B	112.6 (4)	C14—C19B—H19F	109.5
C19A—C14—C18B	93.4 (3)	H19D—C19B—H19F	109.5
C13A—C14—C18B	123.3 (3)	H19E—C19B—H19F	109.5
C13B—C14—C19B	100.2 (6)	H2W1—O1W—H1W1	111 (2)
C16—O2—C1—C6	−1.71 (17)	O5B—C11—C15—C14	−6.8 (3)
C16—O2—C1—C2	178.53 (10)	C13B—C14—C15—C16	172.2 (5)
O2—C1—C2—O1	−1.42 (16)	C19A—C14—C15—C16	42.85 (17)
C6—C1—C2—O1	178.81 (10)	C18A—C14—C15—C16	−80.14 (15)
O2—C1—C2—C3	178.89 (10)	C13A—C14—C15—C16	159.59 (13)
C6—C1—C2—C3	−0.87 (17)	C18B—C14—C15—C16	−62.2 (4)
O1—C2—C3—C4	−178.60 (11)	C19B—C14—C15—C16	58.3 (4)
C1—C2—C3—C4	1.06 (18)	C13B—C14—C15—C11	−10.3 (5)
C2—C3—C4—C5	0.05 (19)	C19A—C14—C15—C11	−139.67 (13)
C3—C4—C5—C6	−1.34 (19)	C18A—C14—C15—C11	97.34 (14)
O2—C1—C6—C5	179.85 (11)	C13A—C14—C15—C11	−22.94 (16)
C2—C1—C6—C5	−0.40 (18)	C18B—C14—C15—C11	115.3 (3)
O2—C1—C6—C7	−1.39 (17)	C19B—C14—C15—C11	−124.2 (4)
C2—C1—C6—C7	178.36 (10)	C1—O2—C16—C15	−176.75 (10)
C4—C5—C6—C1	1.51 (18)	C1—O2—C16—C8	3.63 (16)
C4—C5—C6—C7	−177.21 (11)	C11—C15—C16—O2	179.21 (10)
C1—C6—C7—O3	−177.90 (11)	C14—C15—C16—O2	−3.18 (17)
C5—C6—C7—O3	0.84 (18)	C11—C15—C16—C8	−1.18 (17)
C1—C6—C7—C8	2.41 (16)	C14—C15—C16—C8	176.43 (11)
C5—C6—C7—C8	−178.85 (11)	C9—C8—C16—O2	178.52 (10)
O3—C7—C8—C16	179.76 (11)	C7—C8—C16—O2	−2.47 (17)
C6—C7—C8—C16	−0.56 (16)	C9—C8—C16—C15	−1.07 (17)
O3—C7—C8—C9	−1.26 (18)	C7—C8—C16—C15	177.93 (11)
C6—C7—C8—C9	178.42 (10)	C11—O5A—C12A—O6A	−90.38 (16)
C16—C8—C9—O4	−177.83 (10)	C11—O5A—C12A—C13A	34.57 (19)
C7—C8—C9—O4	3.16 (17)	O6A—C12A—C13A—C14	70.0 (2)
C16—C8—C9—C10	2.57 (17)	O5A—C12A—C13A—C14	−52.97 (19)
C7—C8—C9—C10	−176.45 (11)	C13B—C14—C13A—C12A	−79 (2)
O4—C9—C10—C11	178.68 (11)	C15—C14—C13A—C12A	45.45 (18)
C8—C9—C10—C11	−1.72 (18)	C19A—C14—C13A—C12A	167.66 (16)
C12A—O5A—C11—C10	169.91 (13)	C18A—C14—C13A—C12A	−72.56 (19)
C12A—O5A—C11—C15	−13.5 (2)	C18B—C14—C13A—C12A	−87.2 (4)
C12A—O5A—C11—O5B	37.4 (11)	C19B—C14—C13A—C12A	161.2 (5)
C9—C10—C11—O5A	175.95 (12)	C11—O5B—C12B—O6B	165.2 (8)
C9—C10—C11—C15	−0.73 (19)	C11—O5B—C12B—C13B	54.5 (9)
C9—C10—C11—O5B	−168.5 (3)	C15—C14—C13B—C12B	48.6 (7)
C12B—O5B—C11—O5A	−154.9 (17)	C19A—C14—C13B—C12B	179.6 (5)
C12B—O5B—C11—C10	150.7 (5)	C18A—C14—C13B—C12B	−65.3 (6)
C12B—O5B—C11—C15	−18.3 (8)	C13A—C14—C13B—C12B	109 (3)
O5A—C11—C15—C16	−174.07 (12)	C18B—C14—C13B—C12B	−78.6 (8)
C10—C11—C15—C16	2.13 (17)	C19B—C14—C13B—C12B	170.3 (7)
O5B—C11—C15—C16	170.9 (3)	O6B—C12B—C13B—C14	179.8 (7)
O5A—C11—C15—C14	8.22 (19)	O5B—C12B—C13B—C14	−66.7 (7)
C10—C11—C15—C14	−175.59 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H1O4···O3	0.92 (3)	1.67 (3)	2.5337 (14)	156 (3)
O1—H1O1···O1Wi	0.86 (2)	1.81 (2)	2.6599 (16)	172.5 (19)
O1W—H2W1···O4ii	0.77 (2)	2.13 (2)	2.8756 (16)	166 (2)
O1W—H1W1···O6Aiii	0.88 (3)	1.93 (3)	2.8078 (17)	175 (3)
O6A—H6A···O1iii	0.82 (3)	2.10 (3)	2.8838 (16)	160 (3)
C18A—H18A···O6A	0.96	2.44	3.078 (2)	124
C18A—H18C···O4iv	0.96	2.60	3.530 (2)	164

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H1O4⋯O3	0.92 (3)	1.67 (3)	2.5337 (14)	156 (3)
O1—H1O1⋯O1W i	0.86 (2)	1.81 (2)	2.6599 (16)	172.5 (19)
O1W—H2W1⋯O4ii	0.77 (2)	2.13 (2)	2.8756 (16)	166 (2)
O1W—H1W1⋯O6A iii	0.88 (3)	1.93 (3)	2.8078 (17)	175 (3)
O6A—H6A⋯O1iii	0.82 (3)	2.10 (3)	2.8838 (16)	160 (3)
C18A—H18A⋯O6A	0.96	2.44	3.078 (2)	124
C18A—H18C⋯O4iv	0.96	2.60	3.530 (2)	164

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .