12-(1,1-Dimethyl-2-propen­yl)-5,9,10-trihydr­oxy-2,2-dimethyl-2H,6H-pyrano[3,2-b]xanthen-6-one

In the title compound, C₂₃H₂₂O₆, the xanthene ring system is essentially planar and the chromene ring is in a screw-boat conformation. Position 1 of the 1,1-dimethyl-2-propenyl substituent is coplanar with the attached ring. O—H...O intra­molecular hydrogen bonds are observed in the structure. The mol­ecules form centrosymmetric hydrogen-bonded dimers via weak inter­molecular C—H...O inter­actions. The mol­ecules are linked by inter­molecular O—H...O hydrogen bonds to form a one-dimensional chain along [010].

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.055
• wR factor = 0.145
• Data-to-parameter ratio = 16.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 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
   0 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

S1. Comment

We have previously reported the crystal structures of a xanthone and a modified rotenoid containing the chromene ring, viz 5,9,10-trihydroxy-2,2- dimethyl-12-(3-methylbut-2-enyl)-2H,6H-pyrano[3,2-b]xanthen-6-one methanol solvate (Chantrapromma, Boonnak et al., 2005) and 7a-O-methyldeguelol (Chantrapromma, Fun et al., 2005). The title compound, (I), is another xanthone containing a chromene ring; since it also crystallized in the centrosymmetric space group P2₁/c, this indicates that (I) had been produced by non-enzymatic cyclization of a side chain (Chantrapromma, Boonnak et al., 2005; Chantrapromma, Fun et al., 2005).

Compound (I), macluraxanthone, was isolated from the bark of Cratoxylum formosum ssp. prunifolum, a shrub that was collected from Nhongkhai province in the northeastern part of Thailand. In our continuing search for bioactive compounds obtained from Thai medicinal plants (Chantrapromma et al., 2004; Chantrapromma, Boonnak et al., 2005; Chantrapromma, Fun et al., 2005; Boonnak et al., 2005; Fun et al., 2005; Boonsri et al., 2005), we have investigated C. formosum ssp. pruniflorum. Compound (I) has been reported previously (Monache et al., 1981; Menache et al., 1983; Goh et al., 1992), but its X-ray crystal structure has not yet been reported.

The molecular structure of (I) is shown in Fig. 1. The bond distances and angles show normal values (Allen et al., 1987) and are comparable to those in related structures (Chantrapromma & Boonnak et al., 2005; Ravikumar et al., 1987; Doriguetto et al., 2001).

The xanthene ring system (C1–C13/O3) is almost planar, with all atoms lying within 0.066 (2) Å of the mean plane. The three individual rings of xanthene are each essentially planar, the largest deviations from the ring planes being 0.010 (2), 0.033 (2) and 0.022 (2) Å for atoms C5, C6 and C9, C10 of rings A, B, and C, respectively. The dihedral angle between rings A and B is 2.60 (9)°, rings B and C form a dihedral angle of 5.73 (9)°, and the dihedral angle bewteen rings C and A is 7.77 (9)°. The chromene ring, D, adopts a screw-boat conformation (Cremer & Pople, 1975), with puckering parameters Q = 0.348 (2) Å, θ = 64.0 (3)° and ϕ₂ = 326.7 (4)°. The three hydroxyl groups are each coplanar with the attached rings. Atom C17 of the 1,1-dimethyl-2-propenyl substituent is coplanar with ring C; the torsion angle C8—C9—C10—C17 is 176.93 (18)°.

In the crystal structure, there are intermolecular O1—H1O1···O5(−x, 1/2 + y, −1/2 − z), C17—H17A···O5(−x, 2 − y, −z) and C18—H18A···O4 (−x, 2 − y, −z) hydrogen bonds (Table 1). The molecules are linked by O—H···O intermolecular hydrogen bonds to form infinite chains along the b axis (Fig. 2). These chains form layers approximately parallel to the ab plane and are interconnected by the C—H···O interactions.

S2. Experimental

Air-dried barks of C. formosum ssp. prunifolum (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 10 fractions (F1–F10). Fraction F3 was separated by column chromatography and eluted with 10% acetone-hexane to afford four fractions (3 A three-dimensional). Fraction 3 C was recrystallized from CHCl₃—CH₃OH (4:1 v/v) to yield, after several days, yellow needle-shaped crystals of (I), suitable for single-crystal X-ray diffraction (m.p. 456–457 K).

S3. Refinement

H atoms were placed in calculated positions, with O—H distances of 0.82 Å and C—H distances in the range 0.93–0.96 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. The dashed lines indicate hydrogen bonds.
	Fig. 2. The crystal packing of (I), viewed down the b axis. Hydrogen bonds are shown as dashed lines.

12-(1,1-Dimethyl-2-propenyl)-5,9,10-trihydroxy-2,2-dimethyl-2H,6H- pyrano[3,2-b]xanthen-6-one

Crystal data

C23H22O6	F(000) = 832
Mr = 394.41	Dx = 1.419 Mg m^−3
Monoclinic, P21/c	Melting point = 456–457 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.0220 (8) Å	Cell parameters from 4452 reflections
b = 16.1568 (8) Å	θ = 2.0–28.0°
c = 8.4157 (4) Å	µ = 0.10 mm^−1
β = 104.423 (4)°	T = 100 K
V = 1846.49 (17) Å^3	Needle, yellow
Z = 4	0.46 × 0.08 × 0.04 mm

Data collection

Bruker SMART APEX2 CCD area-detector diffractometer	4452 independent reflections
Radiation source: fine-focus sealed tube	2789 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.076
Detector resolution: 8.33 pixels mm^-1	θmax = 28.0°, θmin = 2.0°
ω scans	h = −18→18
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −21→20
Tmin = 0.990, Tmax = 0.996	l = −11→11
16825 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.145	H-atom parameters constrained
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0623P)^2] where P = (Fo^2 + 2Fc^2)/3
4445 reflections	(Δ/σ)max < 0.001
266 parameters	Δρmax = 0.34 e Å^−3
0 restraints	Δρmin = −0.25 e Å^−3

Special details

Experimental. The data were collected using the Oxford Cryosystem 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	−0.16700 (11)	1.09207 (9)	−0.56072 (17)	0.0214 (4)
H1O1	−0.1266	1.1289	−0.5588	0.032*
O2	0.01745 (11)	1.11209 (9)	−0.35932 (17)	0.0200 (3)
H1O2	0.0744	1.1075	−0.3044	0.030*
O3	0.09651 (10)	0.99086 (9)	−0.13862 (16)	0.0172 (3)
O4	−0.06478 (10)	0.78863 (9)	−0.06809 (18)	0.0197 (3)
O5	0.08288 (10)	0.73333 (8)	0.13765 (17)	0.0189 (3)
H1O5	0.0265	0.7357	0.0798	0.028*
O6	0.38313 (10)	0.88140 (9)	0.22057 (16)	0.0176 (3)
C1	−0.14871 (16)	0.90275 (13)	−0.3253 (2)	0.0175 (4)
H1A	−0.1869	0.8563	−0.3193	0.021*
C2	−0.18486 (16)	0.96376 (13)	−0.4373 (3)	0.0185 (5)
H2A	−0.2474	0.9586	−0.5070	0.022*
C3	−0.12778 (15)	1.03380 (12)	−0.4469 (2)	0.0166 (5)
C4	−0.03367 (15)	1.04212 (12)	−0.3443 (2)	0.0158 (4)
C5	0.00232 (15)	0.97925 (13)	−0.2330 (2)	0.0155 (4)
C6	−0.05423 (15)	0.91002 (12)	−0.2197 (2)	0.0151 (4)
C7	−0.01437 (15)	0.84925 (13)	−0.0945 (2)	0.0167 (4)
C8	0.08641 (15)	0.86223 (12)	−0.0011 (2)	0.0151 (4)
C9	0.14119 (15)	0.93157 (12)	−0.0278 (2)	0.0151 (4)
C10	0.24054 (15)	0.94440 (12)	0.0521 (2)	0.0148 (4)
C11	0.28389 (15)	0.87927 (13)	0.1574 (2)	0.0152 (4)
C12	0.23198 (15)	0.80908 (13)	0.1906 (2)	0.0161 (4)
C13	0.13354 (15)	0.80157 (12)	0.1120 (2)	0.0150 (4)
C14	0.28653 (16)	0.74394 (13)	0.2955 (2)	0.0180 (5)
H14A	0.2564	0.6933	0.3030	0.022*
C15	0.37839 (16)	0.75643 (13)	0.3800 (3)	0.0204 (5)
H15A	0.4138	0.7135	0.4412	0.024*
C16	0.42543 (16)	0.83917 (13)	0.3775 (2)	0.0181 (5)
C17	0.30106 (15)	1.01906 (12)	0.0149 (2)	0.0157 (4)
C18	0.23859 (15)	1.09555 (12)	−0.0437 (3)	0.0177 (5)
H18A	0.1918	1.1089	0.0134	0.021*
C19	0.24341 (16)	1.14510 (14)	−0.1665 (3)	0.0229 (5)
H19A	0.2889	1.1347	−0.2278	0.027*
H19B	0.2013	1.1903	−0.1916	0.027*
C20	0.37533 (16)	1.05243 (13)	0.1712 (3)	0.0198 (5)
H20A	0.4007	1.1049	0.1472	0.030*
H20B	0.4286	1.0139	0.2050	0.030*
H20C	0.3425	1.0591	0.2577	0.030*
C21	0.35830 (16)	0.99066 (14)	−0.1090 (3)	0.0199 (5)
H21A	0.3127	0.9748	−0.2096	0.030*
H21B	0.3991	0.9443	−0.0649	0.030*
H21D	0.3988	1.0352	−0.1299	0.030*
C22	0.53473 (16)	0.83282 (14)	0.3843 (3)	0.0239 (5)
H22A	0.5434	0.8010	0.2926	0.036*
H22B	0.5684	0.8062	0.4846	0.036*
H22C	0.5613	0.8873	0.3801	0.036*
C23	0.40736 (16)	0.89315 (14)	0.5157 (3)	0.0213 (5)
H23A	0.3378	0.8987	0.5040	0.032*
H23B	0.4358	0.9468	0.5106	0.032*
H23C	0.4371	0.8679	0.6194	0.032*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0180 (8)	0.0223 (8)	0.0214 (8)	−0.0017 (6)	0.0002 (6)	0.0065 (6)
O2	0.0165 (8)	0.0191 (8)	0.0223 (8)	−0.0020 (6)	0.0008 (6)	0.0044 (6)
O3	0.0152 (8)	0.0173 (8)	0.0170 (7)	−0.0011 (6)	0.0001 (6)	0.0036 (6)
O4	0.0169 (8)	0.0169 (8)	0.0250 (8)	−0.0012 (6)	0.0046 (6)	0.0029 (6)
O5	0.0166 (8)	0.0173 (8)	0.0215 (8)	−0.0020 (6)	0.0026 (6)	0.0047 (6)
O6	0.0148 (8)	0.0193 (8)	0.0169 (7)	−0.0003 (6)	0.0008 (6)	0.0030 (6)
C1	0.0181 (11)	0.0162 (11)	0.0186 (10)	−0.0015 (8)	0.0053 (9)	−0.0021 (9)
C2	0.0152 (11)	0.0221 (11)	0.0167 (10)	−0.0015 (9)	0.0010 (8)	−0.0025 (9)
C3	0.0178 (11)	0.0165 (11)	0.0152 (10)	0.0031 (8)	0.0034 (9)	0.0005 (8)
C4	0.0169 (11)	0.0144 (10)	0.0173 (10)	−0.0001 (8)	0.0062 (8)	−0.0011 (9)
C5	0.0126 (10)	0.0204 (11)	0.0131 (10)	0.0022 (8)	0.0026 (8)	−0.0014 (9)
C6	0.0152 (11)	0.0161 (11)	0.0150 (10)	0.0021 (8)	0.0054 (8)	−0.0014 (8)
C7	0.0173 (11)	0.0166 (11)	0.0178 (10)	0.0013 (8)	0.0072 (9)	−0.0018 (9)
C8	0.0153 (11)	0.0162 (10)	0.0140 (10)	−0.0002 (8)	0.0043 (8)	−0.0015 (9)
C9	0.0186 (11)	0.0135 (10)	0.0133 (10)	0.0039 (8)	0.0041 (8)	0.0004 (8)
C10	0.0173 (11)	0.0150 (10)	0.0124 (10)	0.0001 (8)	0.0043 (8)	−0.0008 (8)
C11	0.0134 (10)	0.0199 (11)	0.0118 (9)	0.0007 (8)	0.0019 (8)	−0.0034 (8)
C12	0.0199 (11)	0.0156 (10)	0.0121 (10)	0.0003 (8)	0.0025 (8)	−0.0014 (8)
C13	0.0186 (11)	0.0131 (10)	0.0141 (10)	0.0009 (8)	0.0055 (8)	−0.0027 (8)
C14	0.0213 (12)	0.0178 (11)	0.0138 (10)	−0.0010 (9)	0.0022 (9)	0.0000 (9)
C15	0.0223 (12)	0.0194 (11)	0.0180 (11)	0.0035 (9)	0.0024 (9)	0.0044 (9)
C16	0.0178 (11)	0.0212 (11)	0.0132 (10)	0.0015 (9)	−0.0001 (8)	0.0027 (9)
C17	0.0140 (11)	0.0167 (11)	0.0156 (10)	−0.0005 (8)	0.0019 (8)	−0.0003 (9)
C18	0.0137 (11)	0.0193 (11)	0.0186 (10)	−0.0024 (8)	0.0012 (8)	−0.0035 (9)
C19	0.0191 (12)	0.0208 (12)	0.0274 (12)	0.0002 (9)	0.0032 (10)	0.0013 (10)
C20	0.0199 (11)	0.0172 (11)	0.0216 (11)	−0.0032 (9)	0.0037 (9)	0.0009 (9)
C21	0.0185 (11)	0.0203 (11)	0.0212 (11)	−0.0009 (9)	0.0055 (9)	0.0002 (9)
C22	0.0205 (12)	0.0282 (13)	0.0219 (11)	0.0023 (10)	0.0030 (9)	0.0052 (10)
C23	0.0197 (11)	0.0251 (12)	0.0174 (11)	−0.0016 (9)	0.0012 (9)	−0.0007 (9)

Geometric parameters (Å, º)

O1—C3	1.358 (2)	C12—C13	1.379 (3)
O1—H1O1	0.8200	C12—C14	1.462 (3)
O2—C4	1.361 (2)	C14—C15	1.322 (3)
O2—H1O2	0.8200	C14—H14A	0.9300
O3—C5	1.374 (2)	C15—C16	1.493 (3)
O3—C9	1.375 (2)	C15—H15A	0.9300
O4—C7	1.260 (2)	C16—C22	1.523 (3)
O5—C13	1.358 (2)	C16—C23	1.525 (3)
O5—H1O5	0.8200	C17—C18	1.524 (3)
O6—C11	1.361 (2)	C17—C21	1.536 (3)
O6—C16	1.473 (2)	C17—C20	1.556 (3)
C1—C2	1.371 (3)	C18—C19	1.322 (3)
C1—C6	1.405 (3)	C18—H18A	0.9300
C1—H1A	0.9300	C19—H19A	0.9300
C2—C3	1.400 (3)	C19—H19B	0.9300
C2—H2A	0.9300	C20—H20A	0.9600
C3—C4	1.392 (3)	C20—H20B	0.9600
C4—C5	1.389 (3)	C20—H20C	0.9600
C5—C6	1.392 (3)	C21—H21A	0.9600
C6—C7	1.447 (3)	C21—H21B	0.9600
C7—C8	1.451 (3)	C21—H21D	0.9600
C8—C9	1.408 (3)	C22—H22A	0.9600
C8—C13	1.411 (3)	C22—H22B	0.9600
C9—C10	1.403 (3)	C22—H22C	0.9600
C10—C11	1.412 (3)	C23—H23A	0.9600
C10—C17	1.551 (3)	C23—H23B	0.9600
C11—C12	1.413 (3)	C23—H23C	0.9600
C3—O1—H1O1	109.5	C12—C14—H14A	119.7
C4—O2—H1O2	109.5	C14—C15—C16	120.2 (2)
C5—O3—C9	120.47 (16)	C14—C15—H15A	119.9
C13—O5—H1O5	109.5	C16—C15—H15A	119.9
C11—O6—C16	118.85 (15)	O6—C16—C15	110.28 (17)
C2—C1—C6	120.28 (19)	O6—C16—C22	103.98 (16)
C2—C1—H1A	119.9	C15—C16—C22	112.53 (18)
C6—C1—H1A	119.9	O6—C16—C23	108.20 (16)
C1—C2—C3	120.1 (2)	C15—C16—C23	110.09 (17)
C1—C2—H2A	119.9	C22—C16—C23	111.52 (18)
C3—C2—H2A	119.9	C18—C17—C21	112.21 (17)
O1—C3—C4	121.69 (18)	C18—C17—C10	113.38 (16)
O1—C3—C2	117.66 (18)	C21—C17—C10	108.02 (16)
C4—C3—C2	120.64 (19)	C18—C17—C20	101.67 (16)
O2—C4—C5	123.97 (19)	C21—C17—C20	108.92 (17)
O2—C4—C3	117.54 (18)	C10—C17—C20	112.55 (16)
C5—C4—C3	118.48 (18)	C19—C18—C17	127.4 (2)
O3—C5—C4	115.18 (18)	C19—C18—H18A	116.3
O3—C5—C6	123.25 (18)	C17—C18—H18A	116.3
C4—C5—C6	121.57 (19)	C18—C19—H19A	120.0
C5—C6—C1	118.87 (19)	C18—C19—H19B	120.0
C5—C6—C7	118.65 (19)	H19A—C19—H19B	120.0
C1—C6—C7	122.46 (18)	C17—C20—H20A	109.5
O4—C7—C6	121.60 (19)	C17—C20—H20B	109.5
O4—C7—C8	122.06 (19)	H20A—C20—H20B	109.5
C6—C7—C8	116.34 (18)	C17—C20—H20C	109.5
C9—C8—C13	118.55 (19)	H20A—C20—H20C	109.5
C9—C8—C7	121.70 (19)	H20B—C20—H20C	109.5
C13—C8—C7	119.63 (18)	C17—C21—H21A	109.5
O3—C9—C10	116.90 (17)	C17—C21—H21B	109.5
O3—C9—C8	119.22 (18)	H21A—C21—H21B	109.5
C10—C9—C8	123.88 (19)	C17—C21—H21D	109.5
C9—C10—C11	114.29 (18)	H21A—C21—H21D	109.5
C9—C10—C17	123.09 (18)	H21B—C21—H21D	109.5
C11—C10—C17	122.32 (18)	C16—C22—H22A	109.5
O6—C11—C10	117.70 (18)	C16—C22—H22B	109.5
O6—C11—C12	118.05 (18)	H22A—C22—H22B	109.5
C10—C11—C12	124.05 (19)	C16—C22—H22C	109.5
C13—C12—C11	118.62 (19)	H22A—C22—H22C	109.5
C13—C12—C14	122.49 (19)	H22B—C22—H22C	109.5
C11—C12—C14	118.66 (19)	C16—C23—H23A	109.5
O5—C13—C12	119.71 (18)	C16—C23—H23B	109.5
O5—C13—C8	119.73 (18)	H23A—C23—H23B	109.5
C12—C13—C8	120.48 (18)	C16—C23—H23C	109.5
C15—C14—C12	120.5 (2)	H23A—C23—H23C	109.5
C15—C14—H14A	119.7	H23B—C23—H23C	109.5
C6—C1—C2—C3	−0.1 (3)	C16—O6—C11—C10	154.10 (17)
C1—C2—C3—O1	179.59 (18)	C16—O6—C11—C12	−30.8 (2)
C1—C2—C3—C4	0.5 (3)	C9—C10—C11—O6	170.64 (16)
O1—C3—C4—O2	1.5 (3)	C17—C10—C11—O6	−3.3 (3)
C2—C3—C4—O2	−179.50 (17)	C9—C10—C11—C12	−4.1 (3)
O1—C3—C4—C5	−178.76 (17)	C17—C10—C11—C12	−178.06 (18)
C2—C3—C4—C5	0.3 (3)	O6—C11—C12—C13	−172.50 (17)
C9—O3—C5—C4	−177.90 (16)	C10—C11—C12—C13	2.2 (3)
C9—O3—C5—C6	2.2 (3)	O6—C11—C12—C14	2.2 (3)
O2—C4—C5—O3	−1.7 (3)	C10—C11—C12—C14	176.94 (18)
C3—C4—C5—O3	178.53 (17)	C11—C12—C13—O5	177.80 (17)
O2—C4—C5—C6	178.18 (18)	C14—C12—C13—O5	3.3 (3)
C3—C4—C5—C6	−1.6 (3)	C11—C12—C13—C8	1.0 (3)
O3—C5—C6—C1	−178.06 (17)	C14—C12—C13—C8	−173.49 (18)
C4—C5—C6—C1	2.0 (3)	C9—C8—C13—O5	−178.78 (17)
O3—C5—C6—C7	3.5 (3)	C7—C8—C13—O5	−2.8 (3)
C4—C5—C6—C7	−176.38 (18)	C9—C8—C13—C12	−2.0 (3)
C2—C1—C6—C5	−1.2 (3)	C7—C8—C13—C12	173.98 (18)
C2—C1—C6—C7	177.15 (18)	C13—C12—C14—C15	−174.06 (19)
C5—C6—C7—O4	174.51 (18)	C11—C12—C14—C15	11.5 (3)
C1—C6—C7—O4	−3.9 (3)	C12—C14—C15—C16	3.9 (3)
C5—C6—C7—C8	−5.3 (3)	C11—O6—C16—C15	43.4 (2)
C1—C6—C7—C8	176.32 (18)	C11—O6—C16—C22	164.28 (17)
O4—C7—C8—C9	−177.92 (18)	C11—O6—C16—C23	−77.0 (2)
C6—C7—C8—C9	1.9 (3)	C14—C15—C16—O6	−29.4 (3)
O4—C7—C8—C13	6.3 (3)	C14—C15—C16—C22	−145.0 (2)
C6—C7—C8—C13	−173.92 (17)	C14—C15—C16—C23	90.0 (2)
C5—O3—C9—C10	173.95 (17)	C9—C10—C17—C18	28.8 (3)
C5—O3—C9—C8	−5.7 (3)	C11—C10—C17—C18	−157.79 (18)
C13—C8—C9—O3	179.47 (16)	C9—C10—C17—C21	−96.2 (2)
C7—C8—C9—O3	3.6 (3)	C11—C10—C17—C21	77.2 (2)
C13—C8—C9—C10	−0.2 (3)	C9—C10—C17—C20	143.51 (19)
C7—C8—C9—C10	−176.04 (18)	C11—C10—C17—C20	−43.1 (2)
O3—C9—C10—C11	−176.61 (16)	C21—C17—C18—C19	−13.3 (3)
C8—C9—C10—C11	3.0 (3)	C10—C17—C18—C19	−136.0 (2)
O3—C9—C10—C17	−2.7 (3)	C20—C17—C18—C19	102.9 (2)
C8—C9—C10—C17	176.93 (18)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O1···O2	0.82	2.30	2.735 (2)	114
O1—H1O1···O5^i	0.82	1.97	2.720 (2)	153
O2—H1O2···O3	0.82	2.32	2.737 (2)	112
O5—H1O5···O4	0.82	1.77	2.509 (2)	150
C18—H18A···O4^ii	0.93	2.56	3.387 (3)	149
C20—H20B···O6	0.96	2.25	2.792 (3)	115
C23—H23A···O1^ii	0.96	2.56	3.492 (3)	164

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