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Acta Crystallogr Sect E Struct Rep Online. 2009 December 1; 65(Pt 12): o3276–o3277.
Published online 2009 November 28. doi:  10.1107/S1600536809050715
PMCID: PMC2971965

5,7-Dihydr­oxy-3,6,8-trimethoxy­flavone

Abstract

The title compound (systematic name: 5,7-dihydr­oxy-3,6,8-trimeth­oxy-4H-chromen-4-one), C18H16O7, is a flavone that was isolated from Ainsliaea henryi. There are two mol­ecules in the asymmetric unit, one of which has a disordered meth­oxy group [occupancy ratio 0.681 (9):0.319 (9)]. Both mol­ecules have an intra­molecular O—H(...)O hydrogen bond. In the crystal, mol­ecules are linked into O—H(...)O hydrogen-bonded chains parallel to [110].

Related literature

For similar compounds and background information, see: Chinese Materia Medica (2007 [triangle]); Ali et al. (1979 [triangle]); Cubukcu & Bingol (1984 [triangle]); Guerreiro et al. (1982 [triangle]); Horie et al. (1995 [triangle]); Jakupovic et al. (1989 [triangle]); Lavault & Richomme (2004 [triangle]); Mericli et al. (1986 [triangle]); Torrenegra et al. (1980 [triangle]); Urzua et al. (1995 [triangle]); Wollenweber et al. (1993 [triangle], 2008 [triangle]). For the anti­fungal activity of the title compound, see: Tomas-Lorente et al. (1989 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o3276-scheme1.jpg

Experimental

Crystal data

  • C18H16O7
  • M r = 344.31
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o3276-efi1.jpg
  • a = 10.147 (4) Å
  • b = 11.493 (4) Å
  • c = 14.134 (5) Å
  • α = 74.233 (5)°
  • β = 86.461 (5)°
  • γ = 86.845 (5)°
  • V = 1582.0 (10) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 293 K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.967, T max = 0.978
  • 7698 measured reflections
  • 5590 independent reflections
  • 3283 reflections with I > 2σ(I)
  • R int = 0.042

Refinement

  • R[F 2 > 2σ(F 2)] = 0.061
  • wR(F 2) = 0.171
  • S = 0.96
  • 5590 reflections
  • 481 parameters
  • 6 restraints
  • H-atom parameters constrained
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.35 e Å−3

Data collection: SMART (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809050715/pk2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050715/pk2205Isup2.hkl

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

Acknowledgments

The authors thank Dr Jing-Mei Wang (Center of Analysis and Measurement, Fudan University, Shanghai) for the structure analysis.

supplementary crystallographic information

Comment

Ainsliaea henryi Diels is mainly distributed in the south-west of China. The whole plant of Ainsliaea henryi has been used in Chinese folk medicine to treat cough, asthma and lumbago (Chinese Materia Medica, 2007). The chemical constituents of this plant have not all been reported previously. Our chemical investigation of this plant for bioactive components resulted in the isolation of the title compound, which was previously obtained from the flowers of Gnaphalium elegans (Torrenegra et al., 1980). The molecular structure is shown in Fig. 1. Bond lengths and angles are within normal ranges.

Experimental

The dry powders (5 kg) of the whole plant of Ainsliaea henryi were refluxed for 1 h with 95% ethanol (50L) three times. After removal of the ethanol under reduced pressure, the extract was suspended in water and then partitioned with petroleum ether, chloroform, ethyl acetate and n-butanol. The chloroform soluble fraction (30 g) was subjected to silica gel column chromatography using gradient elution (petroleum ether/acetone, 15:1 to 2:1, v/v). 5,7-Dihydroxy-3,6,8-trimethoxyflavone was obtained from the fraction eluted by petroleum ether/acetone (2:1). Single crystals suitable for X-ray diffraction analysis were obtained by slow evaporation from acetone after two weeks at room temperature.

Refinement

The hydroxyl H atoms attached to O2 was located in a difference Fourier map and refined isotropically with a constraint distance 0.82 Å to the related oxygen atoms. The remaining H atoms were placed in calculated positions with C—H distances in the range 0.93–0.98 Å. The Uiso values were set equal to 1.5Ueq (C,O) for methyl and hydroxyl H atoms and 1.2Ueq(C) for the remaining H atoms.

Figures

Fig. 1.
The molecular structure showing the atom-labelling scheme with displacement ellipsoids drawn at the 30% probability level. H atoms are shown as small spheres of arbitrary radius.

Crystal data

C18H16O7Z = 4
Mr = 344.31F(000) = 720
Triclinic, P1Dx = 1.446 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.147 (4) ÅCell parameters from 688 reflections
b = 11.493 (4) Åθ = 2.7–25.1°
c = 14.134 (5) ŵ = 0.11 mm1
α = 74.233 (5)°T = 293 K
β = 86.461 (5)°Block, yellow
γ = 86.845 (5)°0.30 × 0.20 × 0.20 mm
V = 1582.0 (10) Å3

Data collection

Bruker SMART APEX CCD area-detector diffractometer5590 independent reflections
Radiation source: fine-focus sealed tube3283 reflections with I > 2σ(I)
graphiteRint = 0.042
[var phi] and ω scansθmax = 25.2°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −12→12
Tmin = 0.967, Tmax = 0.978k = −13→13
7698 measured reflectionsl = −16→9

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171H-atom parameters constrained
S = 0.96w = 1/[σ2(Fo2) + (0.0916P)2] where P = (Fo2 + 2Fc2)/3
5590 reflections(Δ/σ)max < 0.001
481 parametersΔρmax = 0.25 e Å3
6 restraintsΔρmin = −0.35 e Å3
0 constraints

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 > 2σ(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 (Å2)

xyzUiso*/UeqOcc. (<1)
O2A0.2156 (5)0.6030 (5)0.0119 (3)0.0541 (13)0.681 (9)
C16A0.1025 (6)0.5890 (7)0.0772 (5)0.081 (2)0.681 (9)
H16A0.06140.51530.07870.121*0.681 (9)
H16B0.04120.65630.05500.121*0.681 (9)
H16C0.12820.58620.14200.121*0.681 (9)
O2B0.1539 (9)0.5492 (8)0.0303 (7)0.054 (3)0.319 (9)
C16B0.1933 (16)0.6617 (11)0.0412 (15)0.091 (5)0.319 (9)
H16D0.26720.64790.08270.136*0.319 (9)
H16E0.12110.69930.07060.136*0.319 (9)
H16F0.21810.7137−0.02220.136*0.319 (9)
O10.33194 (18)0.44978 (17)0.17638 (13)0.0552 (5)
O30.2267 (2)0.5264 (2)−0.15835 (14)0.0758 (7)
H30.17150.5729−0.14180.114*
O40.39213 (19)0.34365 (19)−0.18117 (13)0.0630 (6)
O50.52258 (19)0.20267 (18)−0.02531 (14)0.0594 (5)
H50.54870.16290.02810.089*
O60.57099 (19)0.15879 (17)0.15881 (14)0.0604 (6)
O70.52849 (17)0.21483 (16)0.33769 (13)0.0507 (5)
C10.3942 (2)0.3804 (2)0.25738 (19)0.0439 (6)
C20.3477 (3)0.4194 (2)0.0884 (2)0.0485 (7)
C30.2788 (3)0.4914 (3)0.0111 (2)0.0583 (8)
C40.2931 (3)0.4636 (3)−0.0788 (2)0.0553 (7)
C50.3765 (3)0.3673 (3)−0.09125 (19)0.0488 (7)
C60.4439 (2)0.2966 (2)−0.0127 (2)0.0463 (7)
C70.4305 (2)0.3227 (2)0.07893 (19)0.0423 (6)
C80.4973 (2)0.2472 (2)0.1637 (2)0.0451 (6)
C90.4720 (2)0.2829 (2)0.25352 (19)0.0430 (6)
C100.3644 (2)0.4280 (2)0.34344 (19)0.0413 (6)
C110.3612 (3)0.5518 (2)0.3333 (2)0.0524 (7)
H110.37710.60560.27180.063*
C120.3346 (3)0.5944 (3)0.4150 (3)0.0644 (9)
H120.33420.67700.40870.077*
C130.3085 (3)0.5153 (3)0.5058 (3)0.0695 (9)
H130.29110.54470.56070.083*
C140.3080 (3)0.3933 (3)0.5155 (2)0.0652 (9)
H140.28810.34030.57670.078*
C150.3369 (3)0.3492 (3)0.4351 (2)0.0492 (7)
H150.33800.26630.44220.059*
C170.2965 (3)0.2655 (4)−0.1966 (3)0.0887 (12)
H17A0.29530.1933−0.14300.133*
H17B0.31880.2446−0.25710.133*
H17C0.21080.3058−0.20020.133*
C180.6633 (3)0.2394 (3)0.3434 (2)0.0677 (9)
H18A0.71600.21220.29420.102*
H18B0.69300.19760.40740.102*
H18C0.67190.32480.33260.102*
O110.17209 (16)0.07702 (15)0.40008 (13)0.0471 (5)
O120.34604 (18)−0.09955 (16)0.38200 (13)0.0538 (5)
O130.4014 (2)−0.13712 (18)0.20014 (14)0.0615 (6)
H10.4080−0.14140.14310.092*
O140.28707 (19)0.00309 (19)0.03475 (14)0.0652 (6)
O150.1047 (2)0.1880 (2)0.05288 (14)0.0686 (6)
H20.05900.24180.06810.103*
O17−0.06171 (16)0.33282 (17)0.35675 (14)0.0568 (5)
O16−0.01670 (19)0.30149 (18)0.17101 (14)0.0652 (6)
C210.0844 (2)0.1638 (2)0.4174 (2)0.0449 (7)
C220.2006 (2)0.0650 (2)0.30716 (19)0.0427 (6)
C230.2919 (2)−0.0251 (2)0.29875 (19)0.0435 (6)
C240.3162 (2)−0.0457 (2)0.2067 (2)0.0478 (7)
C250.2532 (3)0.0272 (3)0.1242 (2)0.0502 (7)
C260.1650 (3)0.1182 (3)0.1336 (2)0.0496 (7)
C270.1367 (2)0.1396 (2)0.22674 (19)0.0435 (6)
C280.0448 (2)0.2327 (2)0.2411 (2)0.0476 (7)
C290.0255 (2)0.2440 (2)0.3408 (2)0.0476 (7)
C300.0705 (2)0.1546 (2)0.5235 (2)0.0470 (7)
C31−0.0251 (3)0.2212 (3)0.5644 (2)0.0623 (8)
H31−0.08330.27440.52370.075*
C32−0.0339 (3)0.2089 (3)0.6642 (2)0.0686 (9)
H32−0.09740.25460.69030.082*
C330.0498 (3)0.1302 (3)0.7255 (2)0.0675 (9)
H330.04320.12250.79280.081*
C340.1440 (3)0.0619 (3)0.6870 (2)0.0675 (9)
H340.20100.00810.72840.081*
C350.1534 (3)0.0740 (3)0.5870 (2)0.0590 (8)
H350.21660.02730.56170.071*
C360.4841 (3)−0.0855 (3)0.3886 (2)0.0706 (9)
H36A0.5339−0.12440.34510.106*
H36B0.5090−0.12150.45500.106*
H36C0.5022−0.00090.37030.106*
C370.1887 (4)−0.0458 (4)−0.0052 (3)0.1063 (14)
H37A0.1590−0.11800.04160.159*
H37B0.2233−0.0650−0.06410.159*
H37C0.11580.0119−0.02060.159*
C38−0.0057 (3)0.4495 (3)0.3365 (3)0.0771 (10)
H38A0.05230.45020.38750.116*
H38B−0.07520.51020.33410.116*
H38C0.04330.46620.27430.116*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O2A0.065 (3)0.046 (3)0.046 (2)0.014 (2)−0.0035 (18)−0.0042 (19)
C16A0.073 (4)0.081 (5)0.073 (4)0.025 (4)0.012 (3)−0.004 (3)
O2B0.049 (6)0.053 (5)0.056 (5)0.001 (4)−0.002 (4)−0.011 (4)
C16B0.080 (11)0.056 (9)0.144 (14)0.010 (8)−0.032 (10)−0.037 (10)
O10.0649 (12)0.0613 (12)0.0418 (11)0.0228 (10)−0.0135 (9)−0.0206 (9)
O30.0831 (16)0.0953 (17)0.0435 (12)0.0396 (13)−0.0134 (11)−0.0153 (11)
O40.0627 (13)0.0872 (16)0.0391 (12)0.0051 (11)0.0069 (9)−0.0210 (11)
O50.0621 (12)0.0675 (14)0.0502 (12)0.0222 (10)−0.0046 (10)−0.0231 (11)
O60.0674 (13)0.0582 (13)0.0559 (12)0.0258 (11)−0.0103 (10)−0.0198 (10)
O70.0533 (11)0.0500 (11)0.0460 (11)0.0072 (9)−0.0111 (9)−0.0081 (9)
C10.0457 (15)0.0435 (16)0.0430 (16)0.0035 (13)−0.0115 (12)−0.0116 (13)
C20.0491 (16)0.0544 (17)0.0439 (17)0.0087 (13)−0.0065 (13)−0.0178 (14)
C30.0642 (19)0.064 (2)0.0463 (18)0.0266 (16)−0.0108 (14)−0.0185 (15)
C40.0522 (17)0.064 (2)0.0446 (17)0.0107 (15)−0.0066 (14)−0.0086 (15)
C50.0432 (15)0.0645 (19)0.0382 (16)0.0014 (14)−0.0005 (12)−0.0140 (14)
C60.0389 (14)0.0518 (17)0.0488 (17)0.0053 (13)−0.0018 (12)−0.0160 (14)
C70.0401 (14)0.0438 (15)0.0434 (16)0.0012 (12)−0.0061 (12)−0.0122 (12)
C80.0414 (15)0.0434 (16)0.0510 (17)0.0056 (13)−0.0070 (12)−0.0138 (13)
C90.0442 (15)0.0423 (15)0.0421 (16)0.0009 (12)−0.0117 (12)−0.0092 (12)
C100.0368 (14)0.0470 (16)0.0407 (15)0.0022 (12)−0.0034 (11)−0.0135 (13)
C110.0503 (16)0.0504 (17)0.0556 (18)−0.0009 (13)0.0001 (13)−0.0138 (14)
C120.0611 (19)0.058 (2)0.085 (3)−0.0021 (15)0.0023 (17)−0.039 (2)
C130.072 (2)0.088 (3)0.061 (2)0.0083 (18)0.0002 (17)−0.045 (2)
C140.072 (2)0.079 (2)0.0424 (18)0.0060 (17)0.0007 (15)−0.0148 (16)
C150.0513 (16)0.0505 (17)0.0456 (17)0.0030 (13)−0.0058 (13)−0.0128 (14)
C170.084 (2)0.124 (3)0.077 (3)0.006 (2)−0.018 (2)−0.058 (2)
C180.0559 (19)0.082 (2)0.066 (2)0.0076 (17)−0.0229 (16)−0.0194 (17)
O110.0491 (10)0.0463 (11)0.0465 (11)0.0086 (9)−0.0069 (8)−0.0144 (9)
O120.0581 (12)0.0522 (11)0.0445 (11)0.0141 (9)−0.0080 (9)−0.0037 (9)
O130.0733 (13)0.0622 (13)0.0485 (12)0.0293 (11)−0.0090 (10)−0.0188 (10)
O140.0605 (13)0.0839 (15)0.0515 (13)0.0176 (11)−0.0041 (10)−0.0227 (11)
O150.0735 (15)0.0762 (15)0.0498 (12)0.0290 (11)−0.0159 (11)−0.0095 (11)
O170.0416 (10)0.0568 (13)0.0751 (14)0.0130 (9)−0.0060 (9)−0.0251 (11)
O160.0634 (13)0.0673 (14)0.0600 (13)0.0266 (11)−0.0135 (10)−0.0120 (11)
C210.0351 (14)0.0437 (16)0.0577 (18)0.0010 (12)−0.0053 (13)−0.0165 (14)
C220.0413 (14)0.0433 (15)0.0439 (16)−0.0026 (12)−0.0056 (12)−0.0112 (13)
C230.0447 (15)0.0409 (15)0.0426 (16)0.0045 (12)−0.0101 (12)−0.0066 (12)
C240.0456 (16)0.0443 (16)0.0504 (18)0.0052 (13)−0.0058 (13)−0.0079 (13)
C250.0519 (17)0.0545 (18)0.0427 (17)0.0053 (14)−0.0034 (13)−0.0121 (14)
C260.0464 (16)0.0540 (17)0.0452 (17)0.0060 (14)−0.0107 (13)−0.0075 (13)
C270.0398 (14)0.0418 (15)0.0468 (16)0.0014 (12)−0.0069 (12)−0.0078 (12)
C280.0404 (15)0.0457 (16)0.0547 (18)0.0037 (13)−0.0122 (13)−0.0088 (14)
C290.0354 (14)0.0453 (16)0.0653 (19)0.0042 (12)−0.0078 (13)−0.0200 (14)
C300.0413 (15)0.0505 (17)0.0528 (18)−0.0055 (13)−0.0010 (13)−0.0194 (14)
C310.0537 (18)0.070 (2)0.067 (2)0.0045 (15)−0.0012 (15)−0.0253 (17)
C320.061 (2)0.086 (2)0.065 (2)−0.0013 (18)0.0100 (17)−0.0343 (19)
C330.070 (2)0.084 (2)0.053 (2)−0.0173 (19)0.0077 (17)−0.0248 (18)
C340.075 (2)0.077 (2)0.048 (2)0.0015 (18)−0.0066 (16)−0.0123 (17)
C350.0560 (18)0.061 (2)0.061 (2)0.0049 (15)−0.0029 (15)−0.0196 (16)
C360.067 (2)0.067 (2)0.074 (2)0.0077 (17)−0.0307 (17)−0.0090 (17)
C370.077 (3)0.174 (4)0.091 (3)0.020 (3)−0.019 (2)−0.077 (3)
C380.070 (2)0.050 (2)0.111 (3)0.0058 (17)0.0011 (19)−0.0235 (19)

Geometric parameters (Å, °)

O2A—C31.404 (5)C18—H18B0.9599
O2A—C16A1.416 (7)C18—H18C0.9599
C16A—H16A0.9599O11—C211.362 (3)
C16A—H16B0.9599O11—C221.369 (3)
C16A—H16C0.9599O12—C231.378 (3)
O2B—C16B1.425 (13)O12—C361.431 (3)
O2B—C31.444 (8)O13—C241.343 (3)
C16B—H16D0.9599O13—H10.8200
C16B—H16E0.9599O14—C251.386 (3)
C16B—H16F0.9599O14—C371.391 (4)
O1—C11.372 (3)O15—C261.361 (3)
O1—C21.378 (3)O15—H20.8200
O3—C41.356 (3)O17—C291.370 (3)
O3—H30.8200O17—C381.435 (3)
O4—C51.368 (3)O16—C281.262 (3)
O4—C171.423 (4)C21—C291.363 (4)
O5—C61.352 (3)C21—C301.473 (4)
O5—H50.8200C22—C231.376 (3)
O6—C81.243 (3)C22—C271.395 (4)
O7—C91.373 (3)C23—C241.389 (3)
O7—C181.423 (3)C24—C251.404 (4)
C1—C91.346 (3)C25—C261.367 (4)
C1—C101.473 (3)C26—C271.414 (4)
C2—C31.381 (4)C27—C281.429 (4)
C2—C71.387 (3)C28—C291.450 (4)
C3—C41.390 (4)C30—C351.388 (4)
C4—C51.398 (4)C30—C311.396 (4)
C5—C61.379 (4)C31—C321.378 (4)
C6—C71.404 (3)C31—H310.9300
C7—C81.456 (4)C32—C331.367 (5)
C8—C91.441 (3)C32—H320.9300
C10—C151.386 (4)C33—C341.382 (4)
C10—C111.390 (4)C33—H330.9300
C11—C121.378 (4)C34—C351.380 (4)
C11—H110.9300C34—H340.9300
C12—C131.376 (4)C35—H350.9300
C12—H120.9300C36—H36A0.9599
C13—C141.372 (4)C36—H36B0.9599
C13—H130.9300C36—H36C0.9599
C14—C151.375 (4)C37—H37A0.9599
C14—H140.9300C37—H37B0.9599
C15—H150.9300C37—H37C0.9599
C17—H17A0.9599C38—H38A0.9599
C17—H17B0.9599C38—H38B0.9599
C17—H17C0.9599C38—H38C0.9599
C18—H18A0.9599
C3—O2A—C16A112.2 (6)H18B—C18—H18C109.5
C16B—O2B—C3102.2 (11)C21—O11—C22121.8 (2)
O2B—C16B—H16D109.5C23—O12—C36114.4 (2)
O2B—C16B—H16E109.5C24—O13—H1109.5
H16D—C16B—H16E109.5C25—O14—C37115.6 (2)
O2B—C16B—H16F109.5C26—O15—H2109.5
H16D—C16B—H16F109.5C29—O17—C38113.8 (2)
H16E—C16B—H16F109.5O11—C21—C29119.9 (2)
C1—O1—C2119.78 (19)O11—C21—C30110.4 (2)
C4—O3—H3109.5C29—C21—C30129.7 (2)
C5—O4—C17113.5 (2)O11—C22—C23116.5 (2)
C6—O5—H5109.5O11—C22—C27120.7 (2)
C9—O7—C18113.8 (2)C23—C22—C27122.8 (2)
C9—C1—O1121.8 (2)C22—C23—O12119.7 (2)
C9—C1—C10127.0 (2)C22—C23—C24118.1 (2)
O1—C1—C10111.2 (2)O12—C23—C24121.9 (2)
O1—C2—C3116.3 (2)O13—C24—C23117.6 (2)
O1—C2—C7121.0 (2)O13—C24—C25121.8 (2)
C3—C2—C7122.6 (2)C23—C24—C25120.6 (2)
C2—C3—C4117.8 (2)C26—C25—O14122.8 (2)
C2—C3—O2A124.0 (3)C26—C25—C24120.5 (2)
C4—C3—O2A117.1 (3)O14—C25—C24116.7 (2)
C2—C3—O2B119.9 (4)O15—C26—C25119.7 (2)
C4—C3—O2B115.5 (4)O15—C26—C27120.2 (2)
O3—C4—C3122.4 (2)C25—C26—C27120.0 (2)
O3—C4—C5116.5 (2)C22—C27—C26117.9 (2)
C3—C4—C5121.2 (3)C22—C27—C28119.6 (2)
O4—C5—C6120.0 (2)C26—C27—C28122.5 (2)
O4—C5—C4120.2 (2)O16—C28—C27122.0 (3)
C6—C5—C4119.8 (2)O16—C28—C29121.6 (2)
O5—C6—C5119.3 (2)C27—C28—C29116.4 (2)
O5—C6—C7120.7 (2)C21—C29—O17120.7 (3)
C5—C6—C7120.0 (2)C21—C29—C28121.4 (2)
C2—C7—C6118.6 (2)O17—C29—C28117.8 (2)
C2—C7—C8120.3 (2)C35—C30—C31117.8 (3)
C6—C7—C8121.1 (2)C35—C30—C21119.1 (2)
O6—C8—C9122.6 (2)C31—C30—C21123.1 (3)
O6—C8—C7122.4 (2)C32—C31—C30120.7 (3)
C9—C8—C7115.0 (2)C32—C31—H31119.7
C1—C9—O7119.2 (2)C30—C31—H31119.7
C1—C9—C8122.0 (2)C33—C32—C31120.7 (3)
O7—C9—C8118.8 (2)C33—C32—H32119.7
C15—C10—C11119.5 (2)C31—C32—H32119.7
C15—C10—C1120.0 (2)C32—C33—C34119.7 (3)
C11—C10—C1120.5 (2)C32—C33—H33120.1
C12—C11—C10119.5 (3)C34—C33—H33120.1
C12—C11—H11120.2C35—C34—C33119.8 (3)
C10—C11—H11120.2C35—C34—H34120.1
C13—C12—C11120.5 (3)C33—C34—H34120.1
C13—C12—H12119.8C34—C35—C30121.2 (3)
C11—C12—H12119.8C34—C35—H35119.4
C14—C13—C12120.1 (3)C30—C35—H35119.4
C14—C13—H13120.0O12—C36—H36A109.5
C12—C13—H13120.0O12—C36—H36B109.5
C13—C14—C15120.2 (3)H36A—C36—H36B109.5
C13—C14—H14119.9O12—C36—H36C109.5
C15—C14—H14119.9H36A—C36—H36C109.5
C14—C15—C10120.2 (3)H36B—C36—H36C109.5
C14—C15—H15119.9O14—C37—H37A109.5
C10—C15—H15119.9O14—C37—H37B109.5
O4—C17—H17A109.5H37A—C37—H37B109.5
O4—C17—H17B109.5O14—C37—H37C109.5
H17A—C17—H17B109.5H37A—C37—H37C109.5
O4—C17—H17C109.5H37B—C37—H37C109.5
H17A—C17—H17C109.5O17—C38—H38A109.5
H17B—C17—H17C109.5O17—C38—H38B109.5
O7—C18—H18A109.5H38A—C38—H38B109.5
O7—C18—H18B109.5O17—C38—H38C109.5
H18A—C18—H18B109.5H38A—C38—H38C109.5
O7—C18—H18C109.5H38B—C38—H38C109.5
H18A—C18—H18C109.5
C2—O1—C1—C90.5 (4)C12—C13—C14—C151.6 (5)
C2—O1—C1—C10−179.9 (2)C13—C14—C15—C10−1.1 (4)
C1—O1—C2—C3178.1 (3)C11—C10—C15—C14−0.6 (4)
C1—O1—C2—C7−2.9 (4)C1—C10—C15—C14−179.5 (2)
O1—C2—C3—C4179.7 (3)C22—O11—C21—C29−2.0 (4)
C7—C2—C3—C40.8 (5)C22—O11—C21—C30178.8 (2)
O1—C2—C3—O2A12.1 (5)C21—O11—C22—C23179.2 (2)
C7—C2—C3—O2A−166.8 (4)C21—O11—C22—C27−2.2 (3)
O1—C2—C3—O2B−30.4 (6)O11—C22—C23—O122.0 (4)
C7—C2—C3—O2B150.6 (5)C27—C22—C23—O12−176.6 (2)
C16A—O2A—C3—C2−70.4 (7)O11—C22—C23—C24175.4 (2)
C16A—O2A—C3—C4121.9 (5)C27—C22—C23—C24−3.1 (4)
C16A—O2A—C3—O2B25.1 (6)C36—O12—C23—C22−113.0 (3)
C16B—O2B—C3—C290.0 (11)C36—O12—C23—C2473.8 (3)
C16B—O2B—C3—C4−119.5 (9)C22—C23—C24—O13−177.3 (2)
C16B—O2B—C3—O2A−17.8 (8)O12—C23—C24—O13−4.0 (4)
C2—C3—C4—O3178.0 (3)C22—C23—C24—C252.7 (4)
O2A—C3—C4—O3−13.5 (5)O12—C23—C24—C25176.0 (2)
O2B—C3—C4—O326.8 (6)C37—O14—C25—C26−70.2 (4)
C2—C3—C4—C5−1.3 (5)C37—O14—C25—C24111.0 (3)
O2A—C3—C4—C5167.2 (3)O13—C24—C25—C26178.8 (3)
O2B—C3—C4—C5−152.5 (5)C23—C24—C25—C26−1.2 (4)
C17—O4—C5—C692.7 (3)O13—C24—C25—O14−2.4 (4)
C17—O4—C5—C4−87.7 (3)C23—C24—C25—O14177.6 (2)
O3—C4—C5—O42.6 (4)O14—C25—C26—O151.3 (4)
C3—C4—C5—O4−178.1 (3)C24—C25—C26—O15−180.0 (3)
O3—C4—C5—C6−177.8 (3)O14—C25—C26—C27−178.7 (2)
C3—C4—C5—C61.6 (4)C24—C25—C26—C270.0 (4)
O4—C5—C6—O5−1.4 (4)O11—C22—C27—C26−176.5 (2)
C4—C5—C6—O5178.9 (2)C23—C22—C27—C262.0 (4)
O4—C5—C6—C7178.4 (2)O11—C22—C27—C282.6 (4)
C4—C5—C6—C7−1.2 (4)C23—C22—C27—C28−178.9 (2)
O1—C2—C7—C6−179.4 (2)O15—C26—C27—C22179.6 (2)
C3—C2—C7—C6−0.5 (4)C25—C26—C27—C22−0.3 (4)
O1—C2—C7—C83.2 (4)O15—C26—C27—C280.5 (4)
C3—C2—C7—C8−177.9 (3)C25—C26—C27—C28−179.5 (2)
O5—C6—C7—C2−179.5 (2)C22—C27—C28—O16−179.1 (2)
C5—C6—C7—C20.7 (4)C26—C27—C28—O160.0 (4)
O5—C6—C7—C8−2.1 (4)C22—C27—C28—C290.8 (4)
C5—C6—C7—C8178.1 (2)C26—C27—C28—C29179.9 (2)
C2—C7—C8—O6179.1 (2)O11—C21—C29—O17−179.2 (2)
C6—C7—C8—O61.7 (4)C30—C21—C29—O17−0.1 (4)
C2—C7—C8—C9−1.1 (4)O11—C21—C29—C285.6 (4)
C6—C7—C8—C9−178.5 (2)C30—C21—C29—C28−175.3 (2)
O1—C1—C9—O7−178.1 (2)C38—O17—C29—C21101.0 (3)
C10—C1—C9—O72.4 (4)C38—O17—C29—C28−83.6 (3)
O1—C1—C9—C81.6 (4)O16—C28—C29—C21175.0 (3)
C10—C1—C9—C8−177.9 (2)C27—C28—C29—C21−4.9 (4)
C18—O7—C9—C1−100.6 (3)O16—C28—C29—O17−0.3 (4)
C18—O7—C9—C879.7 (3)C27—C28—C29—O17179.8 (2)
O6—C8—C9—C1178.5 (3)O11—C21—C30—C357.0 (3)
C7—C8—C9—C1−1.2 (4)C29—C21—C30—C35−172.1 (3)
O6—C8—C9—O7−1.8 (4)O11—C21—C30—C31−171.4 (2)
C7—C8—C9—O7178.4 (2)C29—C21—C30—C319.5 (4)
C9—C1—C10—C15−42.8 (4)C35—C30—C31—C321.5 (4)
O1—C1—C10—C15137.6 (2)C21—C30—C31—C32179.9 (3)
C9—C1—C10—C11138.3 (3)C30—C31—C32—C33−0.8 (5)
O1—C1—C10—C11−41.3 (3)C31—C32—C33—C34−0.1 (5)
C15—C10—C11—C121.8 (4)C32—C33—C34—C350.2 (5)
C1—C10—C11—C12−179.3 (2)C33—C34—C35—C300.6 (5)
C10—C11—C12—C13−1.3 (4)C31—C30—C35—C34−1.4 (4)
C11—C12—C13—C14−0.4 (5)C21—C30—C35—C34−179.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O3—H3···O16i0.822.062.806 (3)152
O3—H3···O2A0.822.362.772 (5)112
O3—H3···O2B0.822.372.799 (9)114
O5—H5···O60.821.862.586 (3)146
O13—H1···O5ii0.822.052.825 (3)158
O13—H1···O140.822.292.736 (3)115
O15—H2···O160.821.882.600 (3)147

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: PK2205).

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