1,6-Dihydr­oxy-3,7-dimeth­oxy-2,8-bis­(3-methyl-2-buten­yl)-9H-xanthen-9-one

The title compound, C₂₅H₂₈O₆, β-mangostin, is a xanthone which was isolated from Cratoxylum formosum ssp. pruniforum. O—H...O and C—H...O intra­molecular hydrogen bonds are observed in the mol­ecular structure. In the crystal packing, inversion-related mol­ecules are stacked along the a axis with C—H...π and π–π inter­actions.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.140
• Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT142_ALERT_4_C su on b - Axis Small or Missing (x 100000) .....         10 Ang.
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

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S1. Comment

In our search for bioactive compounds from medicinal plants, we have investigated Cratoxylum formosum ssp. pruniflorum, which has been used for traditional medicine in Southeast Asia (Usher et al., 1984). The main components of this plant are xanthones and anthraquinones. We have previously reported the crystal structures of an anthraquinone and xanthones which were isolated from this plant, viz 3-O-(geranyl)anthraquinone (Boonnak, Chantrapromma, Fun, Anjum et al., 2005), xanthone V₁ (Chantrapromma et al., 2005), prunifloxanthone A (Boonnak, Chantrapromma, Fun & Karalai, 2005) and macluraxanthone (Fun et al., 2006). The title compound, (I), β-mangostin, is another xanthone which is a secondary metabolite occurring in this plant. It has previously been isolated from Garcinia mangostana (Asai et al., 1995) and Cratoxylum cochinchinense (Nguyen & Harrison, 1999). Compound (I) has exhibited cytotoxicity against human leukaemia HL 60 cells (Matsumoto et al., 2003) and has antiproliferative effects against human colon cancer DLD-1 cells (Matsumoto et al., 2005).

The present single-crystal structure determination of (I) is part of our on-going search for bioactive compounds from Thai medicinal plants (Chantrapromma et al., 2003, 2004, 2005; Boonnak, Chantrapromma, Fun, Anjum et al., 2005; Boonnak, Chantrapromma, Fun & Karalai, 2005; Fun et al., 2005, 2006). The structure-activity relationship (SAR) of xanthone derivatives will be investigated further.

The molecular structure of (I) is shown in Fig. 1, and selected bond distances and angles are given in Table 1. The bond distances and angles show normal values (Allen et al., 1987) and are comparable with those in closely related structures (Boonnak, Chantrapromma, Fun & Chatchanok, 2005; Chantrapromma et al., 2005; Fun et al., 2006).

The xanthene ring system of (I) (C1–C13/O3) is almost planar, with all atoms lying within 0.088 (1) Å of the mean plane. The dihedral angle between the two benzene rings of xanthene is 3.97 (5)°. The two hydroxyl groups are each coplanar with the attached rings. The methoxy group attached at atom C3 is coplanar with the xanthene ring system, with a C20—O6—C3—C2 torsion angle of 179.94 (11)°, while the other methoxy group attached at atom C12 is twisted away, with a C19–O5–C12–C11 torsion angle of −94.83 (13)°, indicating a (-)-anticlinal conformation (Fig. 1).

The two 3-methylbut-2-enyl substituents are attached to the xanthene ring system at C2 and C13; the torsion angles C1–C2–C21–C22 and C12–C13–C14—C15 are 100.42 (13) and 98.57 (12)°, respectively, both indicating a (+)-anticlinal conformation (Fig. 1). The attachment of the two 3-methylbut-2-enyl substituents is different from that observed in prunifloxanthone A (Boonnak, Chantrapromma, Fun & Karalai, 2005), in which one of them is in a (+)-anticlinal conformation and the other in a (-)-anticlinal conformation. This is due to the attachment of a methoxy group at atom C12 in (I) compared with a hydroxyl group attached at the same position in prunifloxanthone A. We expect that these differences would affect the bioactivities of these compounds.

O1—H1O1···O2 and O4—H1O4···O5 intramolecular hydrogen bonds generate S(6) and S(5) ring motifs, respectively (Bernstein et al., 1995). There are also intramolecular C—H···O interactions present: C14—H14A···O2 generates an S(6) ring motif, C14—H14B···O5 generates an S(5) ring motif and C21—H21B···O1 generates an S(5) ring motif (Table 2). The crystal structure is stabilized by C—H···π interactions involving the C8–C13 benzene ring (centroid Cg1). The xanthene ring systems of inversion-related molecules are stacked in such a way that the centroids of the O3/C5–C9 ring at (x, y, z) and the C1–C6 benzene ring at (1 − x,-y,1 − z) are 3.5697 (6) Å apart, indicating significant π–π interaction (Fig. 2).

S2. Experimental

Air-dried roots of C. formosum ssp. pruniflorum (4 kg) were ground and extracted with hexane and CH₂Cl₂ (2 × 20 l for each solvent) for 5 d at room temperature. The residue obtained after evaporation of the solvent was subjected to quick column chromatography over silica gel and eluted with a gradient of EtOAc–hexane to afford ten fractions (F1–F10). Fraction F2 was separated by column chromatography (CC) and eluted with 100% CH₂Cl₂ to afford four fractions (2 A–two-dimensional). Fraction 2 A was further purified by CC with 30% EtOAc–hexane to give compound (I). Compound (I) was recrystallized from CHCl₃–CH₃OH (4:1 v/v) to yield, after several days, yellow needle-shaped single-crystals (m.p. 445–447 K).

S3. Refinement

Atom H1O4 was located in a difference map and refined isotropically. The remaining H atoms were positioned geometrically and allowed to ride on their parent atoms, with O—H = 0.82 Å and C—H = 0.93–0.97 Å. The U_iso(H) values were constrained to be 1.5U_eq of the carrier atom for hydroxyl and methyl H atoms, and 1.2U_eq for the remaining H atoms.

Computing details

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXTL (Sheldrick, 1998); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

Figures

	Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids and the atomic numbering. Dashed lines indicate hydrogen bonds.
	Fig. 2. The crystal packing of (I), viewed down the a axis. Hydrogen bonds are shown as dashed lines.

1,6-Dihydroxy-3,7-dimethoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one

Crystal data

C25H28O6	Z = 2
Mr = 424.27	F(000) = 452
Triclinic, P1	Dx = 1.309 Mg m^−3
Hall symbol: -P 1	Melting point = 445–447 K
a = 7.8938 (1) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.1976 (1) Å	Cell parameters from 5720 reflections
c = 13.7937 (2) Å	θ = 1.5–29.0°
α = 79.311 (1)°	µ = 0.09 mm^−1
β = 80.926 (1)°	T = 100 K
γ = 87.850 (1)°	Needle, yellow
V = 1077.40 (2) Å^3	0.50 × 0.28 × 0.23 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	5720 independent reflections
Radiation source: fine-focus sealed tube	4623 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
Detector resolution: 8.33 pixels mm^-1	θmax = 29.0°, θmin = 1.5°
ω scans	h = −10→10
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −13→13
Tmin = 0.969, Tmax = 0.979	l = −18→18
16706 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ^2(Fo^2) + (0.0749P)^2 + 0.1769P] where P = (Fo^2 + 2Fc^2)/3
5720 reflections	(Δ/σ)max = 0.001
291 parameters	Δρmax = 0.30 e Å^−3
0 restraints	Δρmin = −0.21 e Å^−3

Special details

Experimental. The data were collected with the Oxford Cyrosystem Cobra low-temperature attachment

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.56817 (13)	0.26595 (9)	0.33464 (7)	0.0476 (2)
H1O1	0.5492	0.3111	0.3786	0.071*
O2	0.56808 (13)	0.32975 (9)	0.50530 (7)	0.0502 (2)
O3	0.78715 (11)	−0.03314 (8)	0.59857 (6)	0.03704 (19)
O4	0.78030 (14)	0.03519 (10)	0.92394 (7)	0.0510 (3)
H1O4	0.753 (3)	0.096 (2)	0.9588 (17)	0.093 (7)*
O5	0.63229 (11)	0.27839 (9)	0.88553 (6)	0.0429 (2)
O6	0.78391 (12)	−0.15344 (9)	0.28254 (7)	0.0458 (2)
C1	0.64106 (14)	0.14889 (11)	0.37044 (8)	0.0334 (2)
C2	0.67944 (14)	0.05629 (11)	0.30825 (8)	0.0340 (2)
C3	0.75272 (14)	−0.06629 (11)	0.34706 (8)	0.0347 (2)
C4	0.78828 (15)	−0.09603 (11)	0.44443 (8)	0.0360 (2)
H4	0.8363	−0.1778	0.4689	0.043*
C5	0.74976 (14)	0.00012 (11)	0.50364 (8)	0.0318 (2)
C6	0.67570 (14)	0.12306 (10)	0.47054 (8)	0.0314 (2)
C7	0.63607 (14)	0.22030 (11)	0.53537 (8)	0.0336 (2)
C8	0.67746 (13)	0.18158 (10)	0.63669 (8)	0.0310 (2)
C9	0.74985 (14)	0.05417 (11)	0.66330 (8)	0.0319 (2)
C10	0.79042 (15)	0.00587 (11)	0.75780 (8)	0.0367 (2)
H10	0.8449	−0.0764	0.7719	0.044*
C11	0.74791 (15)	0.08299 (12)	0.83007 (8)	0.0364 (2)
C12	0.67072 (14)	0.20900 (11)	0.80712 (8)	0.0341 (2)
C13	0.64127 (13)	0.26295 (11)	0.71148 (8)	0.0322 (2)
C14	0.58846 (15)	0.40903 (11)	0.68901 (9)	0.0372 (2)
H14A	0.5023	0.4203	0.6451	0.045*
H14B	0.5395	0.4386	0.7504	0.045*
C15	0.74385 (16)	0.49067 (11)	0.63991 (9)	0.0403 (3)
H15	0.7817	0.4874	0.5730	0.048*
C16	0.83292 (17)	0.56687 (12)	0.68156 (11)	0.0458 (3)
C17	0.9924 (2)	0.63696 (16)	0.62400 (16)	0.0701 (5)
H17A	1.0084	0.6217	0.5565	0.105*
H17B	1.0898	0.6028	0.6548	0.105*
H17C	0.9806	0.7310	0.6240	0.105*
C18	0.7855 (3)	0.5911 (2)	0.78640 (13)	0.0748 (5)
H18A	0.6985	0.5292	0.8219	0.112*
H18B	0.7426	0.6807	0.7852	0.112*
H18C	0.8850	0.5790	0.8193	0.112*
C19	0.4588 (2)	0.25895 (19)	0.93526 (12)	0.0634 (4)
H19A	0.4355	0.3149	0.9847	0.095*
H19B	0.4433	0.1672	0.9669	0.095*
H19C	0.3816	0.2818	0.8874	0.095*
C20	0.8581 (2)	−0.27955 (14)	0.31634 (11)	0.0526 (3)
H20A	0.8701	−0.3317	0.2644	0.079*
H20B	0.7854	−0.3254	0.3742	0.079*
H20C	0.9689	−0.2667	0.3333	0.079*
C21	0.64444 (15)	0.08650 (12)	0.20152 (8)	0.0378 (2)
H21A	0.5971	0.0078	0.1859	0.045*
H21B	0.5593	0.1574	0.1952	0.045*
C22	0.80319 (16)	0.12797 (13)	0.12721 (8)	0.0392 (3)
H22	0.8811	0.0604	0.1141	0.047*
C23	0.84422 (17)	0.25062 (14)	0.07827 (9)	0.0446 (3)
C24	1.0069 (2)	0.27493 (18)	0.00411 (12)	0.0635 (4)
H24A	1.0698	0.1926	0.0032	0.095*
H24B	1.0757	0.3388	0.0230	0.095*
H24C	0.9787	0.3088	−0.0612	0.095*
C25	0.7399 (2)	0.37381 (15)	0.09134 (12)	0.0612 (4)
H25A	0.6351	0.3494	0.1358	0.092*
H25B	0.7139	0.4186	0.0277	0.092*
H25C	0.8040	0.4323	0.1188	0.092*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0666 (6)	0.0390 (5)	0.0400 (4)	0.0147 (4)	−0.0180 (4)	−0.0089 (4)
O2	0.0737 (7)	0.0352 (5)	0.0473 (5)	0.0175 (4)	−0.0243 (5)	−0.0132 (4)
O3	0.0483 (5)	0.0312 (4)	0.0346 (4)	0.0075 (3)	−0.0122 (3)	−0.0102 (3)
O4	0.0758 (7)	0.0458 (5)	0.0335 (4)	0.0075 (5)	−0.0161 (4)	−0.0079 (4)
O5	0.0478 (5)	0.0472 (5)	0.0367 (4)	−0.0008 (4)	−0.0032 (4)	−0.0178 (4)
O6	0.0559 (5)	0.0439 (5)	0.0427 (5)	0.0091 (4)	−0.0109 (4)	−0.0202 (4)
C1	0.0345 (5)	0.0323 (5)	0.0334 (5)	−0.0003 (4)	−0.0060 (4)	−0.0055 (4)
C2	0.0330 (5)	0.0373 (6)	0.0324 (5)	−0.0029 (4)	−0.0045 (4)	−0.0080 (4)
C3	0.0337 (5)	0.0366 (5)	0.0360 (5)	−0.0013 (4)	−0.0033 (4)	−0.0134 (4)
C4	0.0398 (6)	0.0315 (5)	0.0385 (5)	0.0051 (4)	−0.0076 (5)	−0.0104 (4)
C5	0.0320 (5)	0.0320 (5)	0.0322 (5)	−0.0008 (4)	−0.0057 (4)	−0.0073 (4)
C6	0.0328 (5)	0.0300 (5)	0.0325 (5)	−0.0007 (4)	−0.0058 (4)	−0.0078 (4)
C7	0.0363 (5)	0.0298 (5)	0.0363 (5)	0.0010 (4)	−0.0080 (4)	−0.0081 (4)
C8	0.0313 (5)	0.0297 (5)	0.0334 (5)	−0.0004 (4)	−0.0059 (4)	−0.0083 (4)
C9	0.0328 (5)	0.0296 (5)	0.0346 (5)	−0.0003 (4)	−0.0055 (4)	−0.0092 (4)
C10	0.0425 (6)	0.0318 (5)	0.0368 (5)	0.0026 (4)	−0.0100 (5)	−0.0064 (4)
C11	0.0402 (6)	0.0377 (6)	0.0322 (5)	−0.0037 (4)	−0.0071 (4)	−0.0066 (4)
C12	0.0341 (5)	0.0353 (5)	0.0347 (5)	−0.0031 (4)	−0.0033 (4)	−0.0120 (4)
C13	0.0288 (5)	0.0323 (5)	0.0371 (5)	−0.0010 (4)	−0.0045 (4)	−0.0106 (4)
C14	0.0388 (6)	0.0338 (5)	0.0422 (6)	0.0059 (4)	−0.0087 (5)	−0.0140 (4)
C15	0.0479 (7)	0.0301 (5)	0.0426 (6)	0.0043 (5)	−0.0037 (5)	−0.0092 (4)
C16	0.0453 (7)	0.0333 (6)	0.0588 (8)	0.0013 (5)	−0.0135 (6)	−0.0034 (5)
C17	0.0550 (9)	0.0444 (8)	0.1042 (14)	−0.0088 (7)	−0.0070 (9)	0.0009 (8)
C18	0.0985 (14)	0.0741 (11)	0.0615 (10)	−0.0284 (10)	−0.0253 (9)	−0.0210 (8)
C19	0.0572 (9)	0.0776 (11)	0.0538 (8)	−0.0012 (8)	0.0113 (7)	−0.0247 (8)
C20	0.0613 (8)	0.0436 (7)	0.0587 (8)	0.0121 (6)	−0.0116 (7)	−0.0246 (6)
C21	0.0381 (6)	0.0438 (6)	0.0339 (5)	−0.0022 (5)	−0.0085 (4)	−0.0104 (4)
C22	0.0410 (6)	0.0463 (6)	0.0316 (5)	0.0022 (5)	−0.0070 (4)	−0.0099 (5)
C23	0.0470 (7)	0.0507 (7)	0.0367 (6)	−0.0043 (5)	−0.0069 (5)	−0.0086 (5)
C24	0.0582 (9)	0.0731 (10)	0.0523 (8)	−0.0146 (8)	0.0031 (7)	−0.0003 (7)
C25	0.0781 (11)	0.0452 (8)	0.0587 (9)	−0.0021 (7)	−0.0056 (8)	−0.0091 (6)

Geometric parameters (Å, º)

O1—C1	1.3489 (13)	C14—H14B	0.97
O1—H1O1	0.82	C15—C16	1.3274 (18)
O2—C7	1.2488 (13)	C15—H15	0.93
O3—C5	1.3663 (13)	C16—C18	1.499 (2)
O3—C9	1.3670 (12)	C16—C17	1.506 (2)
O4—C11	1.3566 (14)	C17—H17A	0.96
O4—H1O4	0.85 (2)	C17—H17B	0.96
O5—C12	1.3881 (13)	C17—H17C	0.96
O5—C19	1.4348 (18)	C18—H18A	0.96
O6—C3	1.3602 (13)	C18—H18B	0.96
O6—C20	1.4217 (16)	C18—H18C	0.96
C1—C2	1.3844 (15)	C19—H19A	0.96
C1—C6	1.4246 (15)	C19—H19B	0.96
C2—C3	1.4067 (16)	C19—H19C	0.96
C2—C21	1.5140 (15)	C20—H20A	0.96
C3—C4	1.3914 (16)	C20—H20B	0.96
C4—C5	1.3846 (15)	C20—H20C	0.96
C4—H4	0.93	C21—C22	1.5078 (17)
C5—C6	1.3924 (15)	C21—H21A	0.97
C6—C7	1.4484 (14)	C21—H21B	0.97
C7—C8	1.4647 (15)	C22—C23	1.3316 (18)
C8—C9	1.4081 (14)	C22—H22	0.93
C8—C13	1.4288 (14)	C23—C25	1.499 (2)
C9—C10	1.3878 (15)	C23—C24	1.5074 (19)
C10—C11	1.3749 (16)	C24—H24A	0.96
C10—H10	0.93	C24—H24B	0.96
C11—C12	1.4049 (16)	C24—H24C	0.96
C12—C13	1.3838 (15)	C25—H25A	0.96
C13—C14	1.5205 (15)	C25—H25B	0.96
C14—C15	1.5039 (17)	C25—H25C	0.96
C14—H14A	0.97
C1—O1—H1O1	109.5	C14—C15—H15	116.4
C5—O3—C9	120.03 (8)	C15—C16—C18	124.13 (13)
C11—O4—H1O4	107.9 (15)	C15—C16—C17	120.94 (14)
C12—O5—C19	112.64 (10)	C18—C16—C17	114.93 (14)
C3—O6—C20	118.14 (10)	C16—C17—H17A	109.5
O1—C1—C2	118.57 (10)	C16—C17—H17B	109.5
O1—C1—C6	119.72 (10)	H17A—C17—H17B	109.5
C2—C1—C6	121.71 (10)	C16—C17—H17C	109.5
C1—C2—C3	118.00 (10)	H17A—C17—H17C	109.5
C1—C2—C21	120.94 (10)	H17B—C17—H17C	109.5
C3—C2—C21	121.07 (10)	C16—C18—H18A	109.5
O6—C3—C4	122.87 (10)	C16—C18—H18B	109.5
O6—C3—C2	114.84 (10)	H18A—C18—H18B	109.5
C4—C3—C2	122.28 (10)	C16—C18—H18C	109.5
C5—C4—C3	117.78 (10)	H18A—C18—H18C	109.5
C5—C4—H4	121.1	H18B—C18—H18C	109.5
C3—C4—H4	121.1	O5—C19—H19A	109.5
O3—C5—C4	115.82 (9)	O5—C19—H19B	109.5
O3—C5—C6	121.11 (9)	H19A—C19—H19B	109.5
C4—C5—C6	123.07 (10)	O5—C19—H19C	109.5
C5—C6—C1	117.16 (10)	H19A—C19—H19C	109.5
C5—C6—C7	121.22 (9)	H19B—C19—H19C	109.5
C1—C6—C7	121.62 (9)	O6—C20—H20A	109.5
O2—C7—C6	120.73 (10)	O6—C20—H20B	109.5
O2—C7—C8	122.92 (10)	H20A—C20—H20B	109.5
C6—C7—C8	116.34 (9)	O6—C20—H20C	109.5
C9—C8—C13	118.07 (9)	H20A—C20—H20C	109.5
C9—C8—C7	118.04 (9)	H20B—C20—H20C	109.5
C13—C8—C7	123.83 (9)	C22—C21—C2	112.75 (9)
O3—C9—C10	113.79 (9)	C22—C21—H21A	109.0
O3—C9—C8	123.23 (9)	C2—C21—H21A	109.0
C10—C9—C8	122.97 (10)	C22—C21—H21B	109.0
C11—C10—C9	118.17 (10)	C2—C21—H21B	109.0
C11—C10—H10	120.9	H21A—C21—H21B	107.8
C9—C10—H10	120.9	C23—C22—C21	127.21 (12)
O4—C11—C10	119.05 (10)	C23—C22—H22	116.4
O4—C11—C12	120.54 (10)	C21—C22—H22	116.4
C10—C11—C12	120.40 (10)	C22—C23—C25	124.85 (13)
C13—C12—O5	122.03 (10)	C22—C23—C24	120.62 (13)
C13—C12—C11	122.14 (10)	C25—C23—C24	114.52 (13)
O5—C12—C11	115.78 (10)	C23—C24—H24A	109.5
C12—C13—C8	117.97 (10)	C23—C24—H24B	109.5
C12—C13—C14	118.56 (10)	H24A—C24—H24B	109.5
C8—C13—C14	123.21 (10)	C23—C24—H24C	109.5
C15—C14—C13	108.98 (9)	H24A—C24—H24C	109.5
C15—C14—H14A	109.9	H24B—C24—H24C	109.5
C13—C14—H14A	109.9	C23—C25—H25A	109.5
C15—C14—H14B	109.9	C23—C25—H25B	109.5
C13—C14—H14B	109.9	H25A—C25—H25B	109.5
H14A—C14—H14B	108.3	C23—C25—H25C	109.5
C16—C15—C14	127.13 (12)	H25A—C25—H25C	109.5
C16—C15—H15	116.4	H25B—C25—H25C	109.5
O1—C1—C2—C3	−178.93 (10)	C5—O3—C9—C8	−1.87 (16)
C6—C1—C2—C3	0.71 (17)	C13—C8—C9—O3	178.85 (9)
O1—C1—C2—C21	1.41 (17)	C7—C8—C9—O3	1.74 (16)
C6—C1—C2—C21	−178.95 (10)	C13—C8—C9—C10	−1.36 (17)
C20—O6—C3—C4	−0.80 (18)	C7—C8—C9—C10	−178.47 (10)
C20—O6—C3—C2	179.94 (11)	O3—C9—C10—C11	−176.04 (10)
C1—C2—C3—O6	178.76 (10)	C8—C9—C10—C11	4.15 (18)
C21—C2—C3—O6	−1.58 (16)	C9—C10—C11—O4	177.40 (11)
C1—C2—C3—C4	−0.50 (17)	C9—C10—C11—C12	−2.07 (17)
C21—C2—C3—C4	179.16 (10)	C19—O5—C12—C13	87.73 (14)
O6—C3—C4—C5	−179.47 (10)	C19—O5—C12—C11	−94.83 (13)
C2—C3—C4—C5	−0.27 (17)	O4—C11—C12—C13	177.68 (11)
C9—O3—C5—C4	−178.43 (9)	C10—C11—C12—C13	−2.86 (18)
C9—O3—C5—C6	0.85 (16)	O4—C11—C12—O5	0.25 (16)
C3—C4—C5—O3	−179.84 (9)	C10—C11—C12—O5	179.71 (10)
C3—C4—C5—C6	0.88 (17)	O5—C12—C13—C8	−177.12 (9)
O3—C5—C6—C1	−179.91 (9)	C11—C12—C13—C8	5.61 (17)
C4—C5—C6—C1	−0.68 (17)	O5—C12—C13—C14	8.53 (16)
O3—C5—C6—C7	0.19 (16)	C11—C12—C13—C14	−168.74 (10)
C4—C5—C6—C7	179.42 (10)	C9—C8—C13—C12	−3.47 (15)
O1—C1—C6—C5	179.49 (10)	C7—C8—C13—C12	173.45 (10)
C2—C1—C6—C5	−0.15 (16)	C9—C8—C13—C14	170.59 (10)
O1—C1—C6—C7	−0.61 (17)	C7—C8—C13—C14	−12.48 (17)
C2—C1—C6—C7	179.75 (10)	C12—C13—C14—C15	98.57 (12)
C5—C6—C7—O2	−179.28 (11)	C8—C13—C14—C15	−75.46 (13)
C1—C6—C7—O2	0.83 (18)	C13—C14—C15—C16	−103.65 (14)
C5—C6—C7—C8	−0.26 (16)	C14—C15—C16—C18	−3.8 (2)
C1—C6—C7—C8	179.84 (9)	C14—C15—C16—C17	176.53 (12)
O2—C7—C8—C9	178.35 (11)	C1—C2—C21—C22	100.42 (13)
C6—C7—C8—C9	−0.64 (15)	C3—C2—C21—C22	−79.23 (14)
O2—C7—C8—C13	1.42 (18)	C2—C21—C22—C23	−104.99 (14)
C6—C7—C8—C13	−177.57 (10)	C21—C22—C23—C25	2.4 (2)
C5—O3—C9—C10	178.33 (9)	C21—C22—C23—C24	−178.49 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.82	1.82	2.5558 (13)	148
O4—H1O4···O5	0.85 (2)	2.21 (2)	2.6994 (14)	117 (2)
C14—H14A···O2	0.97	2.27	2.8283 (15)	116
C14—H14B···O5	0.97	2.43	2.8573 (15)	106
C18—H18A···O5	0.96	2.59	3.413 (2)	144
C21—H21B···O1	0.97	2.40	2.8103 (15)	105
C20—H20C···Cg1^i	0.96	2.84	3.6661 (16)	144
C21—H21A···Cg1^ii	0.97	2.84	3.5627 (13)	132

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