3,5,7-Triacet­oxy-2-(3,4-di­acet­oxy­phen­yl)-4H-1-benzo­pyran-4-one

In the title compound, C₂₅H₂₀O₁₂, commonly known as penta­acetyl­ated quercetin, the benzene ring and one of its meth­oxy substituent groups is disordered (site occupancy ratio 0.523:0.427), with a dihedral angle between the major-disorder component and the benzene ring of the benzo­pyran­one moiety of 10.8 (6)°. In the crystal, C—H...O hydrogen-bonding inter­actions give chains which extend along b.

Key indicators

• Single-crystal X-ray study
• T = 90 K
• Mean [sigma](C-C) = 0.005 Å
• Disorder in main residue
• R factor = 0.062
• wR factor = 0.179
• Data-to-parameter ratio = 9.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT919_ALERT_3_B Reflection # Likely Affected by the Beamstop ...          2 Check
PLAT934_ALERT_3_B Number of (Iobs-Icalc)/SigmaW > 10 Outliers ....          2 Check
PLAT939_ALERT_3_B Large Value of Not (SHELXL) Weight Optimized S .     129.23

Alert level C
PLAT088_ALERT_3_C Poor Data / Parameter Ratio ....................       9.66 Note
PLAT220_ALERT_2_C Large Non-Solvent  C     Ueq(max)/Ueq(min) Range        3.4 Ratio
PLAT220_ALERT_2_C Large Non-Solvent  O     Ueq(max)/Ueq(min) Range        3.1 Ratio
PLAT222_ALERT_3_C Large Non-Solvent  H     Uiso(max)/Uiso(min) ...        4.1 Ratio
PLAT334_ALERT_2_C Small Average Benzene  C-C Dist. C1A    -C14A          1.37 Ang.
PLAT340_ALERT_3_C Low Bond Precision on  C-C Bonds ...............    0.00446 Ang.
PLAT906_ALERT_3_C Large K value in the Analysis of Variance ......     12.052 Check
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.594         20 Report
PLAT913_ALERT_3_C Missing # of Very Strong Reflections in FCF ....          1 Note
PLAT918_ALERT_3_C Reflection(s) with I(obs) much Smaller I(calc) .          2 Check

Alert level G
PLAT002_ALERT_2_G Number of Distance or Angle Restraints on AtSite         10 Note
PLAT003_ALERT_2_G Number of Uiso or Uij Restrained non-H Atoms ...         47 Report
PLAT083_ALERT_2_G SHELXL Second Parameter in WGHT  Unusually Large       6.25 Why ?
PLAT174_ALERT_4_G The CIF-Embedded .res File Contains FLAT Records          2 Report
PLAT176_ALERT_4_G The CIF-Embedded .res File Contains SADI Records          5 Report
PLAT178_ALERT_4_G The CIF-Embedded .res File Contains SIMU Records          1 Report
PLAT301_ALERT_3_G Main Residue  Disorder ............ Percentage =         27 Note
PLAT380_ALERT_4_G Incorrectly? Oriented X(sp2)-Methyl Moiety .....        C7A Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O10    ..  C13     ..       2.95 Ang.
PLAT720_ALERT_4_G Number of Unusual/Non-Standard Labels ..........         10 Note
PLAT811_ALERT_5_G No ADDSYM Analysis: Too Many Excluded Atoms ....          ! Info
PLAT860_ALERT_3_G Number of Least-Squares Restraints .............        775 Note
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) Still          57 %

   0 ALERT level A = Most likely a serious problem - resolve or explain
   3 ALERT level B = A potentially serious problem, consider carefully
  10 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  13 ALERT level G = General information/check it is not something unexpected

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
  13 ALERT type 3 Indicator that the structure quality may be low
   5 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

---

S1. Comment

Quercetin is the most studied and an important class of flavonoid found in vegetables, fruits and grains. Quercitin and its derivatives have been valuable due to their important properties as antioxidative (Chopra et al., 2000), anticarcinogenic (Pereira et al., 1996), anti-inflammatory (Ferry et al., 1996) and anti-aggregatory agents (Pignatelli et al., 2000) and their vasodilating effects (Pérez-Vizcaíno et al., 2002). Acetylated quercetin derivatives were used as HIV-1 integrase inhibitors for the treatment of HIV-1 infection (Li et al., 2014). They were also used to evaluate the cell proliferation inhibition and apoptosis in HL-60 cells (Sakao et al., 2009). Thus, the elucidation of the crystal structures of quercetin derivatives has attracted much attention. Here,we report the crystal structure of the title compound, the pentaacetyl- substituted quercitin derivative, C₂₅H₂₀O₁₂.

In the title compound (Fig. 1), the benzene ring and one of its methoxy substituent groups, defined by C1A—C14A···C2A— O1A—C6AA—O2A is disordered, giving the alternative component C1B—C14B···C2B—O1B—C6B— O2B with a site occupancy factor of 0.523/0.477. The dihedral angle between the major component (A) and the benzene ring of the benzopyranone moiety (defined by C2—C3···C12) is 10.8 (6)°. The conformations of the two acetyl groups A and B are very different [torsion angles C1A/B —C2A/B—O1A/B—C6A/B are 67.6 (12) and −106.1 (11)°, respectively]. In the crystal (Fig. 2), only weak intermolecular C—H···O hydrogen-bonding interactions are present (Table 1), giving chains extending along b.

Related literature

For background and medical applications of quercitin derivatives, see: Chopra et al. (2000); Pereira et al. (1996); Ferry et al. (1996); Pignatelli et al. (2000); Perez-Vizcaino et al. (2002); Li et al. (2014); Sakao et al. (2009).

S2. Experimental

The title compound was synthesized as follows (Fig. 3). Acetic anhydride (1 ml) was added to a solution of quercetin (2 mmol) in anhydrous pyridine (8 ml) at room temperature. The reaction mixture was stirred for 10 h at 343 K. After completion of reaction, the resultant mixture was cooled to room temperature, then poured into ice-cold water. The precipitate was separated by filtration and then washed with ice-cold water. The resulting precipitate was filtered and finally recrystallized from methanol. Single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of an ethanolic solution at room temperature.

m.p. 465–467 K; δ_H (400 MHz CDCl₃) 7.75–7.67 (2H, m), 7.36 (1H, s), 7.33 (1H, J = 1.8 Hz, d), 6.87 (1H, J = 2.1 Hz, d), 2.42 (3H, s), 2.37–2.31 (12H, m). FABMS: MH⁺, 511.

S3. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Disorder was identified in the benzene ring and one of its acetyl substituent groups and the major and minor components A and B were included with refined occupancy factors of 0.523 (5) and 0.477 (5), respectively. Two low-angle reflections were considered to be affected by the beamstop during data collection, prompting a B-Alert in the checkCIF report.

Computing details

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2014 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: Mercury (Macrae et al., 2008) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).

Figures

	Fig. 1. Molecular configuration and atom-numbering scheme for the title compound with displacement ellipsoids drawn at the 40% probability level. The bonds in the minor disordered B portion of the molecule are shown as dashed lines.
	Fig. 2. Crystal packing diagram of the title compound, viewed along the b axis, with hydrogen atoms and the disordered portion omitted for clarity.
	Fig. 3. Reaction scheme for the synthesis of the title compound.

3,5,7-Triacetoxy-2-(3,4-diacetoxyphenyl)-4H-1-benzopyran-4-one

Crystal data

C25H20O12	Dx = 1.435 Mg m^−3
Mr = 512.41	Melting point = 465–467 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 25664 reflections
a = 20.944 (6) Å	θ = 1.7–19.9°
b = 9.316 (3) Å	µ = 0.12 mm^−1
c = 24.309 (7) Å	T = 90 K
V = 4743 (2) Å^3	Prism, yellow
Z = 8	0.30 × 0.20 × 0.15 mm
F(000) = 2128

Data collection

Bruker APEXII CCD diffractometer	4165 independent reflections
Radiation source: fine-focus sealed tube	3329 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
Detector resolution: 8.333 pixels mm^-1	θmax = 25.0°, θmin = 1.7°
ω scans	h = −24→24
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.805, Tmax = 0.983	l = −28→28
42484 measured reflections

Refinement

Refinement on F^2	775 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.062	H-atom parameters constrained
wR(F^2) = 0.179	w = 1/[σ^2(Fo^2) + (0.0743P)^2 + 6.2477P] where P = (Fo^2 + 2Fc^2)/3
S = 1.21	(Δ/σ)max = 0.003
4145 reflections	Δρmax = 0.34 e Å^−3
429 parameters	Δρmin = −0.39 e Å^−3

Special details

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	Occ. (<1)
C1	0.06601 (18)	1.1281 (4)	0.11576 (17)	0.0369 (9)
C2	0.15863 (14)	0.9957 (3)	0.09647 (13)	0.0200 (7)
C3	0.16239 (14)	0.8854 (3)	0.13579 (12)	0.0177 (6)
C4	0.22412 (14)	0.8435 (3)	0.15093 (12)	0.0181 (6)
C5	0.18454 (15)	0.6718 (3)	0.21506 (12)	0.0199 (7)
C9	0.29542 (18)	0.3080 (4)	0.42104 (14)	0.0307 (8)
C10	0.0014 (2)	1.1652 (5)	0.0935 (2)	0.0582 (13)
H10A	−0.0287	1.0927	0.1042	0.087*
H10B	0.0034	1.1704	0.0541	0.087*
H10C	−0.0118	1.2564	0.1080	0.087*
C11	0.21171 (15)	1.0560 (3)	0.07290 (12)	0.0195 (7)
H11	0.2080	1.1275	0.0464	0.023*
C12	0.27162 (14)	1.0068 (3)	0.08978 (12)	0.0172 (6)
C13	0.37350 (15)	1.0017 (4)	0.04557 (13)	0.0226 (7)
C14	0.42571 (16)	1.1000 (4)	0.02728 (14)	0.0309 (8)
H14A	0.4663	1.0584	0.0362	0.046*
H14B	0.4214	1.1908	0.0456	0.046*
H14C	0.4229	1.1140	−0.0118	0.046*
C15	0.27911 (14)	0.9016 (3)	0.12845 (12)	0.0178 (6)
H15	0.3194	0.8703	0.1392	0.021*
C16	0.12419 (14)	0.7042 (3)	0.20045 (12)	0.0199 (7)
C17	0.03850 (16)	0.5420 (4)	0.19534 (14)	0.0286 (8)
C18	−0.0154 (2)	0.4829 (5)	0.22801 (18)	0.0556 (12)
H18A	−0.0424	0.5600	0.2401	0.083*
H18B	0.0010	0.4325	0.2594	0.083*
H18C	−0.0397	0.4179	0.2056	0.083*
C19	0.10733 (14)	0.8136 (3)	0.16025 (12)	0.0186 (7)
C20	0.3000 (2)	0.1807 (4)	0.45795 (15)	0.0466 (11)
H20A	0.3303	0.1138	0.4431	0.070*
H20B	0.2590	0.1355	0.4608	0.070*
H20C	0.3138	0.2109	0.4938	0.070*
C1A	0.2481 (7)	0.371 (2)	0.3341 (8)	0.0212 (19)	0.523 (5)
C2A	0.1875 (3)	0.3714 (7)	0.3196 (3)	0.0214 (13)	0.523 (5)
C3A	0.1651 (3)	0.4643 (8)	0.2808 (3)	0.0210 (14)	0.523 (5)
H3AA	0.1221	0.4626	0.2716	0.025*	0.523 (5)
C4A	0.2058 (14)	0.562 (3)	0.2545 (12)	0.021 (2)	0.523 (5)
C5A	0.2722 (12)	0.5569 (19)	0.2685 (7)	0.021 (2)	0.523 (5)
H5AA	0.3009	0.6171	0.2506	0.025*	0.523 (5)
C6A	0.1296 (3)	0.2842 (7)	0.3962 (3)	0.0299 (15)	0.523 (5)
C7A	0.0733 (8)	0.2110 (15)	0.4167 (7)	0.035 (3)	0.523 (5)
H7AA	0.0580	0.1453	0.3893	0.053*	0.523 (5)
H7AB	0.0840	0.1589	0.4495	0.053*	0.523 (5)
H7AC	0.0407	0.2801	0.4249	0.053*	0.523 (5)
C1B	0.2584 (8)	0.380 (2)	0.3359 (9)	0.021 (2)	0.477 (5)
C2B	0.1922 (4)	0.4237 (9)	0.3362 (3)	0.0271 (15)	0.477 (5)
C3B	0.1683 (4)	0.5189 (9)	0.2988 (3)	0.0247 (16)	0.477 (5)
H3BA	0.1256	0.5462	0.2998	0.030*	0.477 (5)
C4B	0.2102 (16)	0.575 (3)	0.2584 (13)	0.020 (2)	0.477 (5)
C5B	0.2721 (13)	0.538 (2)	0.2600 (8)	0.021 (2)	0.477 (5)
H5BA	0.3003	0.5804	0.2352	0.025*	0.477 (5)
C6B	0.1097 (4)	0.2669 (7)	0.3641 (3)	0.0257 (15)	0.477 (5)
C7B	0.0828 (9)	0.1796 (16)	0.4078 (7)	0.034 (4)	0.477 (5)
H7BA	0.0908	0.2246	0.4426	0.051*	0.477 (5)
H7BB	0.0376	0.1702	0.4023	0.051*	0.477 (5)
H7BC	0.1022	0.0862	0.4072	0.051*	0.477 (5)
O1	0.08826 (13)	1.1645 (3)	0.15904 (12)	0.0444 (7)
O2	0.09928 (10)	1.0439 (2)	0.07868 (9)	0.0276 (6)
O3	0.23438 (9)	0.7396 (2)	0.19011 (8)	0.0198 (5)
O5	0.27204 (11)	0.2696 (2)	0.37146 (9)	0.0297 (6)
O6	0.30964 (17)	0.4278 (3)	0.43146 (12)	0.0604 (10)
O7	0.32388 (10)	1.0796 (2)	0.06773 (9)	0.0204 (5)
O8	0.37262 (11)	0.8752 (3)	0.04125 (10)	0.0323 (6)
O9	0.07285 (10)	0.6385 (2)	0.22703 (9)	0.0234 (5)
O10	0.05366 (12)	0.5113 (3)	0.14961 (10)	0.0360 (6)
O11	0.05105 (10)	0.8403 (2)	0.14948 (9)	0.0257 (5)
O1A	0.1440 (2)	0.2725 (5)	0.34135 (18)	0.0257 (11)	0.523 (5)
O2A	0.1551 (3)	0.3705 (6)	0.4252 (2)	0.0500 (17)	0.523 (5)
C14A	0.2939 (9)	0.4632 (14)	0.3083 (5)	0.022 (2)	0.523 (5)
H14D	0.3368	0.4602	0.3181	0.027*	0.523 (5)
O1B	0.1528 (3)	0.3714 (6)	0.3783 (2)	0.0365 (13)	0.477 (5)
O2B	0.1042 (2)	0.2270 (6)	0.3176 (2)	0.0369 (15)	0.477 (5)
C14B	0.2953 (10)	0.4398 (16)	0.2979 (6)	0.021 (2)	0.477 (5)
H14E	0.3383	0.4148	0.2966	0.026*	0.477 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.034 (2)	0.032 (2)	0.045 (2)	0.0022 (16)	0.0031 (17)	0.0078 (17)
C2	0.0195 (15)	0.0191 (15)	0.0214 (16)	0.0019 (12)	−0.0029 (13)	−0.0015 (12)
C3	0.0219 (15)	0.0173 (15)	0.0140 (14)	0.0006 (12)	0.0012 (12)	−0.0021 (12)
C4	0.0248 (16)	0.0150 (15)	0.0146 (14)	0.0011 (12)	0.0008 (12)	−0.0009 (12)
C5	0.0223 (16)	0.0197 (15)	0.0177 (15)	−0.0027 (13)	0.0044 (12)	0.0013 (12)
C9	0.046 (2)	0.0201 (18)	0.0264 (17)	−0.0003 (15)	−0.0106 (15)	0.0016 (14)
C10	0.037 (2)	0.062 (3)	0.076 (3)	0.017 (2)	0.003 (2)	0.018 (3)
C11	0.0264 (16)	0.0138 (15)	0.0181 (15)	−0.0002 (12)	−0.0015 (13)	0.0023 (12)
C12	0.0228 (16)	0.0127 (14)	0.0160 (14)	−0.0040 (12)	0.0019 (12)	−0.0034 (12)
C13	0.0247 (17)	0.0286 (19)	0.0145 (15)	−0.0010 (14)	0.0018 (13)	0.0011 (13)
C14	0.0236 (18)	0.044 (2)	0.0255 (18)	−0.0108 (16)	0.0051 (14)	−0.0027 (16)
C15	0.0185 (15)	0.0166 (15)	0.0184 (15)	0.0011 (12)	−0.0002 (12)	−0.0024 (12)
C16	0.0213 (16)	0.0193 (15)	0.0190 (15)	−0.0036 (12)	0.0044 (12)	0.0010 (12)
C17	0.0312 (18)	0.0279 (18)	0.0267 (18)	−0.0060 (15)	−0.0012 (15)	0.0064 (15)
C18	0.055 (3)	0.069 (3)	0.043 (2)	−0.033 (2)	0.005 (2)	0.007 (2)
C19	0.0195 (16)	0.0186 (15)	0.0178 (15)	−0.0004 (12)	−0.0004 (12)	−0.0040 (12)
C20	0.091 (3)	0.0222 (19)	0.0269 (19)	−0.004 (2)	−0.018 (2)	0.0061 (16)
C1A	0.033 (4)	0.015 (3)	0.016 (3)	−0.004 (3)	−0.005 (3)	0.000 (3)
C2A	0.026 (3)	0.018 (3)	0.020 (3)	−0.004 (2)	0.000 (2)	−0.001 (2)
C3A	0.023 (3)	0.018 (3)	0.022 (3)	−0.004 (3)	0.000 (3)	0.000 (2)
C4A	0.024 (4)	0.019 (4)	0.019 (4)	−0.003 (3)	0.000 (3)	−0.001 (3)
C5A	0.028 (3)	0.016 (4)	0.018 (4)	−0.005 (3)	−0.002 (4)	−0.003 (3)
C6A	0.034 (3)	0.029 (3)	0.027 (3)	−0.003 (3)	0.005 (3)	0.001 (3)
C7A	0.028 (6)	0.058 (7)	0.020 (5)	−0.014 (5)	0.014 (3)	0.002 (5)
C1B	0.031 (4)	0.015 (3)	0.017 (3)	−0.001 (3)	−0.006 (3)	−0.004 (3)
C2B	0.038 (3)	0.024 (3)	0.019 (3)	−0.011 (3)	−0.001 (3)	0.002 (3)
C3B	0.030 (3)	0.024 (3)	0.020 (3)	−0.008 (3)	0.001 (3)	−0.001 (3)
C4B	0.026 (4)	0.017 (4)	0.018 (4)	−0.007 (3)	0.001 (3)	0.001 (3)
C5B	0.029 (3)	0.015 (4)	0.018 (4)	−0.006 (3)	−0.001 (4)	−0.004 (3)
C6B	0.026 (3)	0.029 (3)	0.023 (3)	0.002 (3)	−0.001 (3)	0.005 (3)
C7B	0.025 (6)	0.050 (6)	0.026 (6)	−0.008 (5)	0.003 (4)	−0.006 (5)
O1	0.0471 (16)	0.0365 (16)	0.0497 (18)	0.0059 (13)	0.0068 (14)	−0.0009 (13)
O2	0.0228 (12)	0.0310 (13)	0.0290 (13)	0.0044 (10)	−0.0031 (10)	0.0084 (10)
O3	0.0189 (11)	0.0204 (11)	0.0200 (11)	0.0001 (9)	0.0016 (8)	0.0067 (9)
O5	0.0512 (15)	0.0180 (12)	0.0199 (11)	0.0003 (10)	−0.0083 (10)	0.0009 (9)
O6	0.112 (3)	0.0216 (15)	0.0476 (17)	−0.0083 (15)	−0.0493 (18)	0.0033 (13)
O7	0.0214 (11)	0.0161 (11)	0.0238 (11)	−0.0030 (9)	0.0033 (9)	0.0017 (9)
O8	0.0392 (14)	0.0251 (14)	0.0326 (14)	0.0042 (11)	0.0131 (11)	0.0013 (11)
O9	0.0208 (11)	0.0291 (12)	0.0205 (11)	−0.0060 (9)	0.0045 (9)	0.0025 (9)
O10	0.0475 (16)	0.0306 (14)	0.0299 (14)	−0.0111 (12)	0.0027 (12)	−0.0028 (11)
O11	0.0201 (12)	0.0267 (13)	0.0303 (13)	−0.0006 (9)	−0.0004 (10)	0.0032 (10)
O1A	0.030 (2)	0.024 (2)	0.024 (2)	−0.006 (2)	−0.002 (2)	0.0069 (18)
O2A	0.070 (4)	0.044 (3)	0.037 (3)	−0.029 (3)	0.023 (3)	−0.014 (3)
C14A	0.029 (3)	0.018 (4)	0.020 (4)	0.001 (3)	−0.007 (3)	−0.006 (3)
O1B	0.048 (3)	0.038 (3)	0.023 (3)	−0.018 (2)	0.000 (2)	0.009 (2)
O2B	0.029 (3)	0.037 (3)	0.045 (3)	−0.007 (2)	0.006 (3)	−0.005 (3)
C14B	0.029 (3)	0.017 (4)	0.018 (4)	0.002 (3)	−0.007 (3)	−0.005 (3)

Geometric parameters (Å, º)

C1—O1	1.200 (5)	C19—O11	1.233 (4)
C1—O2	1.383 (5)	C20—H20A	0.9600
C1—C10	1.497 (6)	C20—H20B	0.9600
C2—C11	1.371 (4)	C20—H20C	0.9600
C2—O2	1.391 (4)	C1A—O5	1.40 (2)
C2—C3	1.406 (4)	C1A—C2A	1.315 (18)
C3—C4	1.400 (4)	C1A—C14A	1.43 (3)
C3—C19	1.459 (4)	C2A—C3A	1.363 (9)
C4—O3	1.375 (4)	C2A—O1A	1.400 (7)
C4—C15	1.385 (4)	C3A—C4A	1.40 (3)
C5—C16	1.347 (4)	C3A—H3AA	0.9300
C5—O3	1.362 (4)	C4A—C5A	1.43 (4)
C5—C4B	1.49 (3)	C5A—C14A	1.38 (2)
C5—C4A	1.47 (3)	C5A—H5AA	0.9300
C9—O6	1.183 (4)	C6A—O2A	1.194 (7)
C9—O5	1.349 (4)	C6A—O1A	1.373 (7)
C9—C20	1.490 (5)	C6A—C7A	1.449 (10)
C10—H10A	0.9600	C7A—H7AA	0.9600
C10—H10B	0.9600	C7A—H7AB	0.9600
C10—H10C	0.9600	C7A—H7AC	0.9600
C11—C12	1.397 (4)	C1B—C14B	1.33 (3)
C11—H11	0.9300	C1B—C2B	1.44 (2)
C12—C15	1.368 (4)	C1B—O5	1.37 (3)
C12—O7	1.394 (4)	C2B—C3B	1.365 (11)
C13—O8	1.184 (4)	C2B—O1B	1.402 (7)
C13—O7	1.377 (4)	C3B—C4B	1.42 (3)
C13—C14	1.494 (4)	C3B—H3BA	0.9300
C14—H14A	0.9600	C4B—C5B	1.34 (5)
C14—H14B	0.9600	C5B—C14B	1.39 (2)
C14—H14C	0.9600	C5B—H5BA	0.9300
C15—H15	0.9300	C6B—O2B	1.197 (7)
C16—O9	1.395 (4)	C6B—O1B	1.371 (7)
C16—C19	1.456 (4)	C6B—C7B	1.450 (11)
C17—O10	1.191 (4)	C7B—H7BA	0.9600
C17—O9	1.386 (4)	C7B—H7BB	0.9600
C17—C18	1.486 (5)	C7B—H7BC	0.9600
C18—H18A	0.9600	C14A—H14D	0.9300
C18—H18B	0.9600	C14B—H14E	0.9300
C18—H18C	0.9600
O1—C1—O2	122.4 (3)	H20B—C20—H20C	109.5
O1—C1—C10	127.0 (4)	O5—C1A—C2A	121.5 (15)
O2—C1—C10	110.6 (4)	O5—C1A—C14A	116.5 (14)
C11—C2—O2	117.6 (3)	C2A—C1A—C14A	122 (2)
C11—C2—C3	122.6 (3)	C3A—C2A—C1A	121.3 (11)
O2—C2—C3	119.9 (3)	C3A—C2A—O1A	117.1 (6)
C4—C3—C2	115.7 (3)	C1A—C2A—O1A	121.5 (11)
C4—C3—C19	119.7 (3)	C2A—C3A—C4A	121.3 (13)
C2—C3—C19	124.6 (3)	C2A—C3A—H3AA	119.4
O3—C4—C15	114.7 (3)	C4A—C3A—H3AA	119.4
O3—C4—C3	121.5 (3)	C5A—C4A—C3A	117 (2)
C15—C4—C3	123.8 (3)	C5A—C4A—C5	118 (2)
C16—C5—O3	119.9 (3)	C3A—C4A—C5	124 (2)
C16—C5—C4B	131.4 (13)	C14A—C5A—C4A	121 (2)
O3—C5—C4B	108.7 (12)	C14A—C5A—H5AA	119.7
C16—C5—C4A	127.8 (12)	C4A—C5A—H5AA	119.7
O3—C5—C4A	112.3 (12)	O2A—C6A—O1A	121.8 (6)
O6—C9—O5	122.2 (3)	O2A—C6A—C7A	118.6 (9)
O6—C9—C20	127.3 (3)	O1A—C6A—C7A	118.4 (9)
O5—C9—C20	110.5 (3)	C6A—C7A—H7AA	109.5
C1—C10—H10A	109.5	C6A—C7A—H7AB	109.5
C1—C10—H10B	109.5	H7AA—C7A—H7AB	109.5
H10A—C10—H10B	109.5	C6A—C7A—H7AC	109.5
C1—C10—H10C	109.5	H7AA—C7A—H7AC	109.5
H10A—C10—H10C	109.5	H7AB—C7A—H7AC	109.5
H10B—C10—H10C	109.5	C14B—C1B—C2B	116 (2)
C2—C11—C12	118.1 (3)	C14B—C1B—O5	129.2 (16)
C2—C11—H11	120.9	C2B—C1B—O5	114.0 (16)
C12—C11—H11	120.9	C3B—C2B—C1B	122.1 (12)
C15—C12—O7	121.5 (3)	C3B—C2B—O1B	119.7 (7)
C15—C12—C11	122.7 (3)	C1B—C2B—O1B	118.1 (12)
O7—C12—C11	115.6 (3)	C2B—C3B—C4B	118.3 (15)
O8—C13—O7	123.2 (3)	C2B—C3B—H3BA	120.8
O8—C13—C14	126.5 (3)	C4B—C3B—H3BA	120.8
O7—C13—C14	110.3 (3)	C5B—C4B—C3B	119 (3)
C13—C14—H14A	109.5	C5B—C4B—C5	122 (3)
C13—C14—H14B	109.5	C3B—C4B—C5	119 (2)
H14A—C14—H14B	109.5	C4B—C5B—C14B	122 (2)
C13—C14—H14C	109.5	C4B—C5B—H5BA	119.2
H14A—C14—H14C	109.5	C14B—C5B—H5BA	119.2
H14B—C14—H14C	109.5	O2B—C6B—O1B	121.4 (7)
C12—C15—C4	117.1 (3)	O2B—C6B—C7B	118.7 (9)
C12—C15—H15	121.4	O1B—C6B—C7B	118.0 (10)
C4—C15—H15	121.4	C6B—C7B—H7BA	109.5
C5—C16—O9	120.2 (3)	C6B—C7B—H7BB	109.5
C5—C16—C19	124.1 (3)	H7BA—C7B—H7BB	109.5
O9—C16—C19	115.5 (3)	C6B—C7B—H7BC	109.5
O10—C17—O9	122.4 (3)	H7BA—C7B—H7BC	109.5
O10—C17—C18	127.8 (3)	H7BB—C7B—H7BC	109.5
O9—C17—C18	109.7 (3)	C1—O2—C2	115.5 (3)
C17—C18—H18A	109.5	C5—O3—C4	121.0 (2)
C17—C18—H18B	109.5	C9—O5—C1A	122.1 (6)
H18A—C18—H18B	109.5	C9—O5—C1B	116.0 (6)
C17—C18—H18C	109.5	C13—O7—C12	119.1 (2)
H18A—C18—H18C	109.5	C17—O9—C16	115.3 (2)
H18B—C18—H18C	109.5	C6A—O1A—C2A	117.3 (5)
O11—C19—C16	121.0 (3)	C5A—C14A—C1A	117.7 (17)
O11—C19—C3	125.2 (3)	C5A—C14A—H14D	121.1
C16—C19—C3	113.7 (3)	C1A—C14A—H14D	121.1
C9—C20—H20A	109.5	C6B—O1B—C2B	116.8 (6)
C9—C20—H20B	109.5	C1B—C14B—C5B	122.4 (19)
H20A—C20—H20B	109.5	C1B—C14B—H14E	118.8
C9—C20—H20C	109.5	C5B—C14B—H14E	118.8
H20A—C20—H20C	109.5
C6A—O1A—C2A—C1A	67.6 (12)	O2—C2—C11—C12	−179.0 (3)
C6A—O1A—C2A—C3A	−115.3 (7)	O2—C2—C3—C19	0.5 (4)
C2A—O1A—C6A—C7A	163.8 (8)	O2—C2—C3—C4	179.7 (3)
C2A—O1A—C6A—O2A	−3.5 (9)	C1A—C2A—C3A—C4A	1 (2)
C6B—O1B—C2B—C1B	−106.1 (11)	O1A—C2A—C3A—C4A	−176.5 (15)
C6B—O1B—C2B—C3B	77.2 (9)	C2—C3—C19—O11	0.2 (5)
C2B—O1B—C6B—C7B	161.1 (10)	C4—C3—C19—C16	1.6 (4)
C2B—O1B—C6B—O2B	−3.1 (11)	C2—C3—C19—C16	−179.3 (3)
C2—O2—C1—C10	−176.3 (3)	C19—C3—C4—C15	177.5 (3)
C1—O2—C2—C11	−108.2 (3)	C2—C3—C4—O3	178.2 (3)
C2—O2—C1—O1	4.3 (5)	C19—C3—C4—O3	−2.6 (4)
C1—O2—C2—C3	74.1 (3)	C2—C3—C4—C15	−1.7 (4)
C5—O3—C4—C15	−179.0 (2)	C4—C3—C19—O11	−179.0 (3)
C4—O3—C5—C4A	178.5 (12)	C2A—C3A—C4A—C5A	2 (3)
C4—O3—C5—C16	1.5 (4)	C2A—C3A—C4A—C5	−175.7 (15)
C5—O3—C4—C3	1.1 (4)	O3—C4—C15—C12	−179.2 (2)
C9—O5—C1A—C14A	70.9 (16)	C3—C4—C15—C12	0.7 (4)
C1A—O5—C9—C20	163.8 (8)	C5A—C4A—C5—C16	−173.0 (13)
C1A—O5—C9—O6	−16.3 (9)	C3A—C4A—C5A—C14A	−3 (3)
C9—O5—C1A—C2A	−115.6 (14)	C5A—C4A—C5—O3	10 (2)
C13—O7—C12—C11	−131.8 (3)	C3A—C4A—C5—C16	5 (3)
C12—O7—C13—C14	−176.9 (3)	C3A—C4A—C5—O3	−171.8 (18)
C12—O7—C13—O8	4.6 (4)	C5—C4A—C5A—C14A	175.2 (16)
C13—O7—C12—C15	52.9 (4)	C4A—C5—C16—C19	−179.0 (14)
C17—O9—C16—C5	−110.5 (3)	C4A—C5—C16—O9	5.6 (15)
C17—O9—C16—C19	73.7 (3)	O3—C5—C16—C19	−2.6 (4)
C16—O9—C17—C18	−178.6 (3)	O3—C5—C16—O9	−178.0 (2)
C16—O9—C17—O10	3.9 (5)	C4A—C5A—C14A—C1A	1 (3)
O5—C1A—C14A—C5A	175.5 (13)	C2—C11—C12—C15	0.2 (4)
C14A—C1A—C2A—C3A	−3 (2)	C2—C11—C12—O7	−175.1 (3)
O5—C1A—C2A—O1A	1 (2)	O7—C12—C15—C4	175.1 (3)
C2A—C1A—C14A—C5A	2 (2)	C11—C12—C15—C4	0.1 (4)
O5—C1A—C2A—C3A	−176.0 (10)	O9—C16—C19—O11	−2.9 (4)
C14A—C1A—C2A—O1A	174.2 (12)	C5—C16—C19—C3	1.0 (4)
C11—C2—C3—C19	−177.2 (3)	O9—C16—C19—C3	176.6 (2)
C11—C2—C3—C4	2.0 (4)	C5—C16—C19—O11	−178.5 (3)
C3—C2—C11—C12	−1.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C3A—H3AA···O9	0.93	2.22	2.842 (7)	124
C5A—H5AA···O3	0.93	2.32	2.675 (18)	102
C7A—H7AB···O8^i	0.96	2.43	3.331 (17)	156
C20—H20A···O2A^ii	0.96	2.33	3.142 (7)	142
C20—H20B···O6^ii	0.96	2.51	3.352 (5)	146

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