(±)-4,12,15,18,26-Penta-hydroxy-13,17-dioxahepta-cyclo-[14.10.0.0.0.0.0.0]hexa-cosa-1,3(14),6(11),7,9,15,19,21,23-nona-ene-5,25-dione monohydrate.

The title compound, C(24)H(14)O(9)·H(2)O, displays a cup-shaped form. The water mol-ecule is disordered over two set of sites with an occupancy ratio of 0.78:0.22. The mol-ecule of the compound has four stereocenters and corresponds to the SSRR/RRSS diastereoisomer. In the mol-ecule, the maximum dihedral angle between the planar benzene rings is 80.40 (4)°. The H atoms of the hy-droxy groups are engaged in hydrogen bonding, forming infinite chains parallel to the a axis. These chains are inter-linked through water mol-ecules, 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 inter-actions result in the formation of a three-dimensional network.

Related literature

For background and related structures, see: Almog et al. (2009 ▶); Yaqub et al. (2010 ▶).

Experimental

Crystal data

C24H14O9·H2O

M = 464.37

Triclinic,

a = 8.2448 (4) Å

b = 11.1558 (7) Å

c = 12.2569 (7) Å

α = 64.571 (2)°

β = 78.126 (1)°

γ = 80.738 (2)°

V = 992.98 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.12 mm−1

T = 296 K

0.24 × 0.16 × 0.14 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.975, T max = 0.983

14323 measured reflections

3592 independent reflections

2717 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.106

S = 1.03

3592 reflections

312 parameters

H-atom parameters constrained

Δρmax = 0.29 e Å−3

Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811009573/dn2665sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811009573/dn2665Isup2.hkl

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

C24H14O9·H2O	Z = 2
Mr = 464.37	F(000) = 480
Triclinic, P1	Dx = 1.553 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2448 (4) Å	Cell parameters from 2717 reflections
b = 11.1558 (7) Å	θ = 2.1–25.3°
c = 12.2569 (7) Å	µ = 0.12 mm−1
α = 64.571 (2)°	T = 296 K
β = 78.126 (1)°	Prisms, white
γ = 80.738 (2)°	0.24 × 0.16 × 0.14 mm
V = 992.98 (10) Å3

Bruker Kappa APEXII CCD diffractometer	3592 independent reflections
Radiation source: fine-focus sealed tube	2717 reflections with I > 2σ(I)
graphite	Rint = 0.039
Detector resolution: 8.10 pixels mm-1	θmax = 25.3°, θmin = 2.1°
ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.975, Tmax = 0.983	l = −14→14
14323 measured reflections

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0477P)2 + 0.3139P] where P = (Fo2 + 2Fc2)/3
3592 reflections	(Δ/σ)max < 0.001
312 parameters	Δρmax = 0.29 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

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 > 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	0.74158 (16)	0.31117 (14)	0.13753 (13)	0.0325 (4)
H1	0.8190	0.3518	0.1328	0.049*
O2	0.44555 (15)	0.20020 (13)	0.18069 (12)	0.0275 (3)
O3	0.23840 (18)	0.07962 (14)	0.18599 (13)	0.0345 (4)
H3	0.2547	0.1146	0.1110	0.052*
O4	0.06749 (16)	0.34145 (16)	0.10489 (12)	0.0340 (4)
H4	0.1297	0.3594	0.0395	0.051*
O5	−0.08231 (19)	0.34995 (16)	0.32765 (14)	0.0470 (4)
O6	0.70474 (15)	0.58630 (14)	0.12331 (12)	0.0278 (3)
O7	0.38306 (18)	0.82777 (14)	0.04490 (13)	0.0367 (4)
H7	0.4280	0.8243	−0.0200	0.055*
O8	0.71372 (18)	0.81081 (15)	0.06590 (12)	0.0348 (4)
H8	0.7947	0.8166	0.0920	0.052*
O9	0.20667 (19)	0.75200 (17)	0.28466 (15)	0.0472 (4)
O10A	0.9905 (3)	0.8676 (3)	0.1058 (3)	0.1166 (15)	0.78
H10A	1.0445	0.8386	0.1654	0.175*	0.78
H10B	1.0535	0.9036	0.0381	0.175*
O10B	1.0286 (3)	0.8307 (3)	0.0423 (3)	0.1166 (15)	0.22
H10C	1.0828	0.8252	−0.0326	0.175*	0.22
C1	0.2922 (2)	0.3946 (2)	0.17679 (16)	0.0237 (4)
C2	0.4482 (2)	0.32831 (19)	0.16793 (16)	0.0229 (4)
C3	0.5959 (2)	0.38453 (19)	0.14809 (16)	0.0229 (4)
C4	0.5743 (2)	0.5138 (2)	0.13981 (16)	0.0236 (4)
C5	0.4192 (2)	0.58264 (19)	0.14865 (16)	0.0239 (4)
C6	0.2742 (2)	0.5243 (2)	0.16695 (17)	0.0254 (4)
H6	0.1701	0.5699	0.1724	0.031*
C7	0.2716 (2)	0.1651 (2)	0.23039 (17)	0.0267 (5)
C8	0.1629 (2)	0.3014 (2)	0.20018 (17)	0.0257 (4)
C9	0.0451 (2)	0.2811 (2)	0.32021 (18)	0.0292 (5)
C10	0.1173 (2)	0.1670 (2)	0.41783 (18)	0.0284 (5)
C11	0.0688 (3)	0.1197 (2)	0.54396 (19)	0.0365 (5)
H11	−0.0191	0.1630	0.5777	0.044*
C12	0.1552 (3)	0.0069 (2)	0.6172 (2)	0.0424 (6)
H12	0.1258	−0.0260	0.7017	0.051*
C13	0.2853 (3)	−0.0581 (2)	0.5666 (2)	0.0415 (6)
H13	0.3413	−0.1343	0.6179	0.050*
C14	0.3335 (3)	−0.0120 (2)	0.44149 (19)	0.0350 (5)
H14	0.4213	−0.0556	0.4080	0.042*
C15	0.2470 (2)	0.1011 (2)	0.36760 (18)	0.0268 (5)
C16	0.6316 (2)	0.7026 (2)	0.15031 (17)	0.0277 (5)
C17	0.4423 (2)	0.7165 (2)	0.14245 (17)	0.0276 (5)
C18	0.3551 (3)	0.7255 (2)	0.26280 (19)	0.0311 (5)
C19	0.4801 (3)	0.6899 (2)	0.34347 (18)	0.0303 (5)
C20	0.6377 (2)	0.6727 (2)	0.28187 (18)	0.0284 (5)
C21	0.7748 (3)	0.6349 (2)	0.34150 (19)	0.0359 (5)
H21	0.8802	0.6208	0.3018	0.043*
C22	0.7509 (3)	0.6189 (2)	0.4618 (2)	0.0426 (6)
H22	0.8420	0.5950	0.5029	0.051*
C23	0.5942 (3)	0.6377 (2)	0.5225 (2)	0.0426 (6)
H23	0.5821	0.6272	0.6031	0.051*
C24	0.4564 (3)	0.6717 (2)	0.46534 (19)	0.0373 (5)
H24	0.3508	0.6822	0.5066	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0166 (7)	0.0386 (9)	0.0433 (9)	−0.0027 (6)	−0.0024 (6)	−0.0186 (7)
O2	0.0203 (7)	0.0296 (8)	0.0319 (8)	−0.0061 (6)	0.0026 (6)	−0.0135 (6)
O3	0.0396 (9)	0.0396 (9)	0.0299 (8)	−0.0151 (7)	0.0011 (7)	−0.0181 (7)
O4	0.0214 (8)	0.0528 (10)	0.0270 (8)	−0.0106 (7)	−0.0038 (6)	−0.0130 (7)
O5	0.0327 (9)	0.0492 (10)	0.0442 (10)	0.0055 (8)	0.0066 (7)	−0.0139 (8)
O6	0.0220 (7)	0.0351 (8)	0.0299 (7)	−0.0086 (6)	0.0005 (6)	−0.0165 (6)
O7	0.0418 (9)	0.0335 (9)	0.0308 (8)	−0.0006 (7)	−0.0062 (7)	−0.0100 (7)
O8	0.0383 (9)	0.0398 (9)	0.0264 (8)	−0.0185 (7)	−0.0032 (6)	−0.0093 (7)
O9	0.0341 (10)	0.0651 (12)	0.0484 (10)	0.0044 (8)	−0.0016 (7)	−0.0338 (9)
O10A	0.102 (2)	0.136 (3)	0.081 (2)	−0.074 (2)	−0.0554 (19)	0.0243 (19)
O10B	0.102 (2)	0.136 (3)	0.081 (2)	−0.074 (2)	−0.0554 (19)	0.0243 (19)
C1	0.0183 (10)	0.0325 (11)	0.0206 (10)	−0.0043 (8)	−0.0019 (7)	−0.0109 (9)
C2	0.0233 (11)	0.0270 (11)	0.0178 (9)	−0.0056 (8)	−0.0005 (7)	−0.0086 (8)
C3	0.0178 (10)	0.0309 (11)	0.0190 (9)	−0.0020 (8)	−0.0016 (7)	−0.0096 (8)
C4	0.0214 (11)	0.0318 (11)	0.0186 (9)	−0.0094 (8)	−0.0002 (7)	−0.0101 (8)
C5	0.0243 (11)	0.0285 (11)	0.0183 (9)	−0.0033 (8)	−0.0021 (7)	−0.0093 (8)
C6	0.0181 (10)	0.0332 (12)	0.0242 (10)	−0.0003 (8)	−0.0025 (8)	−0.0119 (9)
C7	0.0204 (11)	0.0331 (12)	0.0281 (11)	−0.0104 (8)	0.0020 (8)	−0.0137 (9)
C8	0.0171 (10)	0.0362 (12)	0.0243 (10)	−0.0056 (8)	−0.0024 (8)	−0.0119 (9)
C9	0.0224 (11)	0.0352 (12)	0.0318 (11)	−0.0085 (9)	0.0017 (8)	−0.0157 (10)
C10	0.0247 (11)	0.0343 (12)	0.0281 (11)	−0.0103 (9)	0.0002 (8)	−0.0138 (9)
C11	0.0360 (13)	0.0461 (14)	0.0293 (12)	−0.0126 (10)	0.0046 (9)	−0.0183 (11)
C12	0.0475 (15)	0.0511 (15)	0.0250 (11)	−0.0179 (12)	−0.0023 (10)	−0.0089 (11)
C13	0.0397 (14)	0.0397 (14)	0.0356 (13)	−0.0072 (11)	−0.0113 (10)	−0.0026 (11)
C14	0.0300 (12)	0.0332 (12)	0.0378 (12)	−0.0044 (9)	−0.0036 (9)	−0.0109 (10)
C15	0.0237 (11)	0.0306 (11)	0.0283 (11)	−0.0096 (9)	−0.0017 (8)	−0.0124 (9)
C16	0.0290 (11)	0.0300 (11)	0.0250 (10)	−0.0093 (9)	0.0001 (8)	−0.0116 (9)
C17	0.0273 (11)	0.0312 (11)	0.0244 (10)	−0.0035 (9)	−0.0040 (8)	−0.0111 (9)
C18	0.0323 (13)	0.0288 (12)	0.0329 (12)	−0.0048 (9)	0.0014 (9)	−0.0153 (10)
C19	0.0370 (13)	0.0271 (11)	0.0287 (11)	−0.0064 (9)	−0.0005 (9)	−0.0139 (9)
C20	0.0343 (12)	0.0262 (11)	0.0265 (10)	−0.0077 (9)	−0.0028 (9)	−0.0116 (9)
C21	0.0361 (13)	0.0406 (13)	0.0349 (12)	−0.0059 (10)	−0.0078 (10)	−0.0172 (10)
C22	0.0551 (16)	0.0412 (14)	0.0367 (13)	−0.0050 (11)	−0.0176 (11)	−0.0159 (11)
C23	0.0667 (17)	0.0392 (14)	0.0255 (11)	−0.0086 (12)	−0.0077 (11)	−0.0150 (10)
C24	0.0502 (15)	0.0344 (13)	0.0287 (12)	−0.0090 (10)	0.0028 (10)	−0.0161 (10)

O1—C3	1.356 (2)	C7—C15	1.501 (3)
O1—H1	0.8200	C7—C8	1.571 (3)
O2—C2	1.373 (2)	C8—C9	1.535 (3)
O2—C7	1.482 (2)	C9—C10	1.465 (3)
O3—C7	1.369 (2)	C10—C15	1.388 (3)
O3—H3	0.8200	C10—C11	1.393 (3)
O4—C8	1.414 (2)	C11—C12	1.379 (3)
O4—H4	0.8200	C11—H11	0.9300
O5—C9	1.210 (2)	C12—C13	1.387 (3)
O6—C4	1.379 (2)	C12—H12	0.9300
O6—C16	1.481 (2)	C13—C14	1.383 (3)
O7—C17	1.407 (2)	C13—H13	0.9300
O7—H7	0.8200	C14—C15	1.384 (3)
O8—C16	1.374 (2)	C14—H14	0.9300
O8—H8	0.8200	C16—C20	1.510 (3)
O9—C18	1.214 (2)	C16—C17	1.562 (3)
O10A—H10A	0.8488	C17—C18	1.540 (3)
O10A—H10B	0.8501	C18—C19	1.466 (3)
O10B—H10B	0.8488	C19—C20	1.391 (3)
O10B—H10C	0.9573	C19—C24	1.394 (3)
C1—C2	1.385 (3)	C20—C21	1.383 (3)
C1—C6	1.385 (3)	C21—C22	1.382 (3)
C1—C8	1.507 (3)	C21—H21	0.9300
C2—C3	1.389 (3)	C22—C23	1.385 (3)
C3—C4	1.386 (3)	C22—H22	0.9300
C4—C5	1.391 (3)	C23—C24	1.373 (3)
C5—C6	1.385 (3)	C23—H23	0.9300
C5—C17	1.503 (3)	C24—H24	0.9300
C6—H6	0.9300
C3—O1—H1	109.5	C10—C11—H11	121.0
C2—O2—C7	106.21 (13)	C11—C12—C13	120.9 (2)
C7—O3—H3	109.5	C11—C12—H12	119.5
C8—O4—H4	109.5	C13—C12—H12	119.5
C4—O6—C16	106.53 (14)	C14—C13—C12	121.4 (2)
C17—O7—H7	109.5	C14—C13—H13	119.3
C16—O8—H8	109.5	C12—C13—H13	119.3
H10A—O10A—H10B	111.1	C13—C14—C15	117.9 (2)
H10B—O10B—H10C	105.5	C13—C14—H14	121.0
C2—C1—C6	120.97 (17)	C15—C14—H14	121.0
C2—C1—C8	108.59 (17)	C14—C15—C10	120.92 (19)
C6—C1—C8	130.42 (17)	C14—C15—C7	127.30 (18)
O2—C2—C1	114.10 (16)	C10—C15—C7	111.75 (18)
O2—C2—C3	122.06 (17)	O8—C16—O6	107.42 (15)
C1—C2—C3	123.84 (18)	O8—C16—C20	114.67 (16)
O1—C3—C4	127.48 (17)	O6—C16—C20	110.07 (16)
O1—C3—C2	118.53 (17)	O8—C16—C17	113.52 (16)
C4—C3—C2	113.99 (17)	O6—C16—C17	106.15 (14)
O6—C4—C3	123.20 (17)	C20—C16—C17	104.69 (15)
O6—C4—C5	113.39 (17)	O7—C17—C5	115.96 (16)
C3—C4—C5	123.41 (17)	O7—C17—C18	108.19 (16)
C6—C5—C4	121.19 (19)	C5—C17—C18	108.73 (15)
C6—C5—C17	129.73 (18)	O7—C17—C16	117.31 (16)
C4—C5—C17	108.98 (16)	C5—C17—C16	101.66 (15)
C5—C6—C1	116.59 (18)	C18—C17—C16	104.13 (15)
C5—C6—H6	121.7	O9—C18—C19	128.14 (19)
C1—C6—H6	121.7	O9—C18—C17	123.76 (19)
O3—C7—O2	108.40 (14)	C19—C18—C17	108.01 (17)
O3—C7—C15	110.20 (16)	C20—C19—C24	121.3 (2)
O2—C7—C15	110.56 (15)	C20—C19—C18	110.23 (18)
O3—C7—C8	118.18 (16)	C24—C19—C18	128.50 (19)
O2—C7—C8	105.64 (14)	C21—C20—C19	120.31 (19)
C15—C7—C8	103.66 (15)	C21—C20—C16	128.44 (18)
O4—C8—C1	114.40 (16)	C19—C20—C16	111.24 (18)
O4—C8—C9	108.96 (15)	C22—C21—C20	118.1 (2)
C1—C8—C9	111.02 (15)	C22—C21—H21	120.9
O4—C8—C7	116.81 (16)	C20—C21—H21	120.9
C1—C8—C7	101.22 (14)	C21—C22—C23	121.4 (2)
C9—C8—C7	103.80 (15)	C21—C22—H22	119.3
O5—C9—C10	128.69 (18)	C23—C22—H22	119.3
O5—C9—C8	124.02 (19)	C24—C23—C22	121.0 (2)
C10—C9—C8	107.30 (17)	C24—C23—H23	119.5
C15—C10—C11	120.9 (2)	C22—C23—H23	119.5
C15—C10—C9	109.91 (17)	C23—C24—C19	117.8 (2)
C11—C10—C9	129.16 (19)	C23—C24—H24	121.1
C12—C11—C10	118.0 (2)	C19—C24—H24	121.1
C12—C11—H11	121.0
C7—O2—C2—C1	−13.7 (2)	C13—C14—C15—C10	0.8 (3)
C7—O2—C2—C3	166.22 (16)	C13—C14—C15—C7	−176.90 (19)
C6—C1—C2—O2	179.41 (16)	C11—C10—C15—C14	−1.0 (3)
C8—C1—C2—O2	0.8 (2)	C9—C10—C15—C14	−178.79 (17)
C6—C1—C2—C3	−0.5 (3)	C11—C10—C15—C7	176.95 (17)
C8—C1—C2—C3	−179.17 (17)	C9—C10—C15—C7	−0.8 (2)
O2—C2—C3—O1	2.0 (3)	O3—C7—C15—C14	62.6 (2)
C1—C2—C3—O1	−178.11 (16)	O2—C7—C15—C14	−57.2 (3)
O2—C2—C3—C4	−178.83 (16)	C8—C7—C15—C14	−170.02 (19)
C1—C2—C3—C4	1.1 (3)	O3—C7—C15—C10	−115.25 (18)
C16—O6—C4—C3	−166.01 (17)	O2—C7—C15—C10	124.93 (17)
C16—O6—C4—C5	13.3 (2)	C8—C7—C15—C10	12.1 (2)
O1—C3—C4—O6	−2.5 (3)	C4—O6—C16—O8	−140.03 (15)
C2—C3—C4—O6	178.36 (16)	C4—O6—C16—C20	94.49 (17)
O1—C3—C4—C5	178.20 (17)	C4—O6—C16—C17	−18.27 (18)
C2—C3—C4—C5	−0.9 (3)	C6—C5—C17—O7	−64.0 (3)
O6—C4—C5—C6	−179.17 (16)	C4—C5—C17—O7	119.56 (18)
C3—C4—C5—C6	0.2 (3)	C6—C5—C17—C18	58.1 (3)
O6—C4—C5—C17	−2.4 (2)	C4—C5—C17—C18	−118.33 (17)
C3—C4—C5—C17	176.96 (17)	C6—C5—C17—C16	167.58 (19)
C4—C5—C6—C1	0.5 (3)	C4—C5—C17—C16	−8.87 (19)
C17—C5—C6—C1	−175.59 (18)	O8—C16—C17—O7	6.5 (2)
C2—C1—C6—C5	−0.3 (3)	O6—C16—C17—O7	−111.32 (18)
C8—C1—C6—C5	178.02 (18)	C20—C16—C17—O7	132.24 (17)
C2—O2—C7—O3	147.83 (15)	O8—C16—C17—C5	134.01 (16)
C2—O2—C7—C15	−91.28 (18)	O6—C16—C17—C5	16.24 (17)
C2—O2—C7—C8	20.25 (17)	C20—C16—C17—C5	−100.20 (16)
C2—C1—C8—O4	−114.96 (18)	O8—C16—C17—C18	−113.04 (17)
C6—C1—C8—O4	66.6 (3)	O6—C16—C17—C18	129.19 (15)
C2—C1—C8—C9	121.23 (17)	C20—C16—C17—C18	12.75 (19)
C6—C1—C8—C9	−57.3 (3)	O7—C17—C18—O9	45.9 (3)
C2—C1—C8—C7	11.54 (19)	C5—C17—C18—O9	−80.8 (2)
C6—C1—C8—C7	−166.95 (19)	C16—C17—C18—O9	171.4 (2)
O3—C7—C8—O4	−15.6 (2)	O7—C17—C18—C19	−137.08 (16)
O2—C7—C8—O4	105.87 (17)	C5—C17—C18—C19	96.20 (18)
C15—C7—C8—O4	−137.81 (16)	C16—C17—C18—C19	−11.6 (2)
O3—C7—C8—C1	−140.47 (16)	O9—C18—C19—C20	−177.4 (2)
O2—C7—C8—C1	−19.02 (17)	C17—C18—C19—C20	5.8 (2)
C15—C7—C8—C1	97.30 (16)	O9—C18—C19—C24	3.6 (4)
O3—C7—C8—C9	104.36 (18)	C17—C18—C19—C24	−173.2 (2)
O2—C7—C8—C9	−134.19 (14)	C24—C19—C20—C21	0.9 (3)
C15—C7—C8—C9	−17.87 (18)	C18—C19—C20—C21	−178.18 (18)
O4—C8—C9—O5	−37.0 (3)	C24—C19—C20—C16	−178.04 (18)
C1—C8—C9—O5	89.9 (2)	C18—C19—C20—C16	2.9 (2)
C7—C8—C9—O5	−162.1 (2)	O8—C16—C20—C21	−63.9 (3)
O4—C8—C9—C10	143.22 (16)	O6—C16—C20—C21	57.4 (3)
C1—C8—C9—C10	−89.92 (19)	C17—C16—C20—C21	171.1 (2)
C7—C8—C9—C10	18.09 (19)	O8—C16—C20—C19	114.97 (19)
O5—C9—C10—C15	168.8 (2)	O6—C16—C20—C19	−123.79 (17)
C8—C9—C10—C15	−11.4 (2)	C17—C16—C20—C19	−10.1 (2)
O5—C9—C10—C11	−8.7 (4)	C19—C20—C21—C22	−1.8 (3)
C8—C9—C10—C11	171.1 (2)	C16—C20—C21—C22	176.9 (2)
C15—C10—C11—C12	1.0 (3)	C20—C21—C22—C23	1.0 (3)
C9—C10—C11—C12	178.2 (2)	C21—C22—C23—C24	0.7 (4)
C10—C11—C12—C13	−0.6 (3)	C22—C23—C24—C19	−1.6 (3)
C11—C12—C13—C14	0.4 (3)	C20—C19—C24—C23	0.8 (3)
C12—C13—C14—C15	−0.4 (3)	C18—C19—C24—C23	179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O4i	0.82	2.00	2.6885 (18)	141
O3—H3···O8ii	0.82	1.94	2.7559 (19)	177
O4—H4···O6ii	0.82	2.08	2.8964 (18)	176
O7—H7···O2ii	0.82	2.14	2.9548 (19)	175
O8—H8···O10A	0.82	1.86	2.653 (3)	163
O8—H8···O10B	0.82	1.91	2.587 (3)	139
O10A—H10A···O9i	0.85	2.01	2.844 (3)	168
O10B—H10C···O1iii	0.96	2.50	3.357 (5)	148
C11—H11···O9iv	0.93	2.44	3.345 (3)	164
C23—H23···Cg1v	0.93	2.65	3.562 (2)	168

CgI	CgJ	CgI···CgJa	CgI···P(J)b	CgJ···P(I)c	Slippage
Cg1	Cg1vi	3.5314 (11)	3.396	3.396	0.968
Cg2	Cg2vii	3.6525 (14)	3.377	3.377	1.392
Cg3	Cg3v	3.7905 (14)	3.358	3.358	1.758

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O4i	0.82	2.00	2.6885 (18)	141
O3—H3⋯O8ii	0.82	1.94	2.7559 (19)	177
O4—H4⋯O6ii	0.82	2.08	2.8964 (18)	176
O7—H7⋯O2ii	0.82	2.14	2.9548 (19)	175
O8—H8⋯O10A	0.82	1.86	2.653 (3)	163
O8—H8⋯O10B	0.82	1.91	2.587 (3)	139
O10A—H10A⋯O9i	0.85	2.01	2.844 (3)	168
O10B—H10C⋯O1iii	0.96	2.50	3.357 (5)	148
C11—H11⋯O9iv	0.93	2.44	3.345 (3)	164
C23—H23⋯Cg1v	0.93	2.65	3.562 (2)	168

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

Table 2

Table 2 ▶ π-π stacking inter­actions (Å,°)

Cg1, Cg2 and Cg3 are the centroids of the C1–C6, C10–C15 and C19–C24 rings, respectively.

CgI	CgJ	CgI⋯CgJa	CgI⋯P(J)b	CgJ⋯P(I)c	Slippage
Cg1	Cg1vi	3.5314 (11)	3.396	3.396	0.968
Cg2	Cg2vii	3.6525 (14)	3.377	3.377	1.392
Cg3	Cg3v	3.7905 (14)	3.358	3.358	1.758

Symmetry codes: (v) 1 − x, 1 − y, 1 − z; (vi) 1 − x, 1 − y, −z; (vii) −x, −y, 1 − z. Notes: (a) distance between centroids; (b) perpendicular distance of CgI on ring plan J; (c) perpendicular distance of CgJ on ring plan I; (d) slippage = vertical displacement between ring centroids.