Skip to main content
PMC home page
Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2009 Nov 28;65(Pt 12):o3276–o3277. doi: 10.1107/S1600536809050715

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

Hui-Ping Xiong a, Zhi-Jun Wu b,*, Fa-Tang Chen a, Wan-Sheng Chen b
PMCID: PMC2971965  PMID: 21578970

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 ▶); Ali et al. (1979 ▶); Cubukcu & Bingol (1984 ▶); Guerreiro et al. (1982 ▶); Horie et al. (1995 ▶); Jakupovic et al. (1989 ▶); Lavault & Richomme (2004 ▶); Mericli et al. (1986 ▶); Torrenegra et al. (1980 ▶); Urzua et al. (1995 ▶); Wollenweber et al. (1993 ▶, 2008 ▶). For the anti­fungal activity of the title compound, see: Tomas-Lorente et al. (1989 ▶).graphic file with name e-65-o3276-scheme1.jpg

Experimental

Crystal data

  • C18H16O7

  • M r = 344.31

  • Triclinic, Inline graphic

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

Supplementary Material

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

e-65-o3276-sup1.cif (30.6KB, cif)

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

e-65-o3276-Isup2.hkl (273.7KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A D⋯A D—H⋯A
O3—H3⋯O16i 0.82 2.06 2.806 (3) 152
O3—H3⋯O2A 0.82 2.36 2.772 (5) 112
O3—H3⋯O2B 0.82 2.37 2.799 (9) 114
O5—H5⋯O6 0.82 1.86 2.586 (3) 146
O13—H1⋯O5ii 0.82 2.05 2.825 (3) 158
O13—H1⋯O14 0.82 2.29 2.736 (3) 115
O15—H2⋯O16 0.82 1.88 2.600 (3) 147
Open in a new tab

Symmetry codes: (i) Inline graphic; (ii) Inline graphic.

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.

Fig. 1.

Open in a new tab

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

C18H16O7 Z = 4
Mr = 344.31 F(000) = 720
Triclinic, P1 Dx = 1.446 Mg m−3
Hall symbol: -P 1 Mo Kα radiation, λ = 0.71073 Å
a = 10.147 (4) Å Cell parameters from 688 reflections
b = 11.493 (4) Å θ = 2.7–25.1°
c = 14.134 (5) Å µ = 0.11 mm−1
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
Open in a new tab

Data collection

Bruker SMART APEX CCD area-detector diffractometer 5590 independent reflections
Radiation source: fine-focus sealed tube 3283 reflections with I > 2σ(I)
graphite Rint = 0.042
φ and ω scans θmax = 25.2°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) h = −12→12
Tmin = 0.967, Tmax = 0.978 k = −13→13
7698 measured reflections l = −16→9
Open in a new tab

Refinement

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)] = 0.061 Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.171 H-atom parameters constrained
S = 0.96 w = 1/[σ2(Fo2) + (0.0916P)2] where P = (Fo2 + 2Fc2)/3
5590 reflections (Δ/σ)max < 0.001
481 parameters Δρmax = 0.25 e Å−3
6 restraints Δρmin = −0.35 e Å−3
0 constraints
Open in a new tab

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.
Open in a new tab

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

x y z Uiso*/Ueq Occ. (<1)
O2A 0.2156 (5) 0.6030 (5) 0.0119 (3) 0.0541 (13) 0.681 (9)
C16A 0.1025 (6) 0.5890 (7) 0.0772 (5) 0.081 (2) 0.681 (9)
H16A 0.0614 0.5153 0.0787 0.121* 0.681 (9)
H16B 0.0412 0.6563 0.0550 0.121* 0.681 (9)
H16C 0.1282 0.5862 0.1420 0.121* 0.681 (9)
O2B 0.1539 (9) 0.5492 (8) 0.0303 (7) 0.054 (3) 0.319 (9)
C16B 0.1933 (16) 0.6617 (11) 0.0412 (15) 0.091 (5) 0.319 (9)
H16D 0.2672 0.6479 0.0827 0.136* 0.319 (9)
H16E 0.1211 0.6993 0.0706 0.136* 0.319 (9)
H16F 0.2181 0.7137 −0.0222 0.136* 0.319 (9)
O1 0.33194 (18) 0.44978 (17) 0.17638 (13) 0.0552 (5)
O3 0.2267 (2) 0.5264 (2) −0.15835 (14) 0.0758 (7)
H3 0.1715 0.5729 −0.1418 0.114*
O4 0.39213 (19) 0.34365 (19) −0.18117 (13) 0.0630 (6)
O5 0.52258 (19) 0.20267 (18) −0.02531 (14) 0.0594 (5)
H5 0.5487 0.1629 0.0281 0.089*
O6 0.57099 (19) 0.15879 (17) 0.15881 (14) 0.0604 (6)
O7 0.52849 (17) 0.21483 (16) 0.33769 (13) 0.0507 (5)
C1 0.3942 (2) 0.3804 (2) 0.25738 (19) 0.0439 (6)
C2 0.3477 (3) 0.4194 (2) 0.0884 (2) 0.0485 (7)
C3 0.2788 (3) 0.4914 (3) 0.0111 (2) 0.0583 (8)
C4 0.2931 (3) 0.4636 (3) −0.0788 (2) 0.0553 (7)
C5 0.3765 (3) 0.3673 (3) −0.09125 (19) 0.0488 (7)
C6 0.4439 (2) 0.2966 (2) −0.0127 (2) 0.0463 (7)
C7 0.4305 (2) 0.3227 (2) 0.07893 (19) 0.0423 (6)
C8 0.4973 (2) 0.2472 (2) 0.1637 (2) 0.0451 (6)
C9 0.4720 (2) 0.2829 (2) 0.25352 (19) 0.0430 (6)
C10 0.3644 (2) 0.4280 (2) 0.34344 (19) 0.0413 (6)
C11 0.3612 (3) 0.5518 (2) 0.3333 (2) 0.0524 (7)
H11 0.3771 0.6056 0.2718 0.063*
C12 0.3346 (3) 0.5944 (3) 0.4150 (3) 0.0644 (9)
H12 0.3342 0.6770 0.4087 0.077*
C13 0.3085 (3) 0.5153 (3) 0.5058 (3) 0.0695 (9)
H13 0.2911 0.5447 0.5607 0.083*
C14 0.3080 (3) 0.3933 (3) 0.5155 (2) 0.0652 (9)
H14 0.2881 0.3403 0.5767 0.078*
C15 0.3369 (3) 0.3492 (3) 0.4351 (2) 0.0492 (7)
H15 0.3380 0.2663 0.4422 0.059*
C17 0.2965 (3) 0.2655 (4) −0.1966 (3) 0.0887 (12)
H17A 0.2953 0.1933 −0.1430 0.133*
H17B 0.3188 0.2446 −0.2571 0.133*
H17C 0.2108 0.3058 −0.2002 0.133*
C18 0.6633 (3) 0.2394 (3) 0.3434 (2) 0.0677 (9)
H18A 0.7160 0.2122 0.2942 0.102*
H18B 0.6930 0.1976 0.4074 0.102*
H18C 0.6719 0.3248 0.3326 0.102*
O11 0.17209 (16) 0.07702 (15) 0.40008 (13) 0.0471 (5)
O12 0.34604 (18) −0.09955 (16) 0.38200 (13) 0.0538 (5)
O13 0.4014 (2) −0.13712 (18) 0.20014 (14) 0.0615 (6)
H1 0.4080 −0.1414 0.1431 0.092*
O14 0.28707 (19) 0.00309 (19) 0.03475 (14) 0.0652 (6)
O15 0.1047 (2) 0.1880 (2) 0.05288 (14) 0.0686 (6)
H2 0.0590 0.2418 0.0681 0.103*
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)
C21 0.0844 (2) 0.1638 (2) 0.4174 (2) 0.0449 (7)
C22 0.2006 (2) 0.0650 (2) 0.30716 (19) 0.0427 (6)
C23 0.2919 (2) −0.0251 (2) 0.29875 (19) 0.0435 (6)
C24 0.3162 (2) −0.0457 (2) 0.2067 (2) 0.0478 (7)
C25 0.2532 (3) 0.0272 (3) 0.1242 (2) 0.0502 (7)
C26 0.1650 (3) 0.1182 (3) 0.1336 (2) 0.0496 (7)
C27 0.1367 (2) 0.1396 (2) 0.22674 (19) 0.0435 (6)
C28 0.0448 (2) 0.2327 (2) 0.2411 (2) 0.0476 (7)
C29 0.0255 (2) 0.2440 (2) 0.3408 (2) 0.0476 (7)
C30 0.0705 (2) 0.1546 (2) 0.5235 (2) 0.0470 (7)
C31 −0.0251 (3) 0.2212 (3) 0.5644 (2) 0.0623 (8)
H31 −0.0833 0.2744 0.5237 0.075*
C32 −0.0339 (3) 0.2089 (3) 0.6642 (2) 0.0686 (9)
H32 −0.0974 0.2546 0.6903 0.082*
C33 0.0498 (3) 0.1302 (3) 0.7255 (2) 0.0675 (9)
H33 0.0432 0.1225 0.7928 0.081*
C34 0.1440 (3) 0.0619 (3) 0.6870 (2) 0.0675 (9)
H34 0.2010 0.0081 0.7284 0.081*
C35 0.1534 (3) 0.0740 (3) 0.5870 (2) 0.0590 (8)
H35 0.2166 0.0273 0.5617 0.071*
C36 0.4841 (3) −0.0855 (3) 0.3886 (2) 0.0706 (9)
H36A 0.5339 −0.1244 0.3451 0.106*
H36B 0.5090 −0.1215 0.4550 0.106*
H36C 0.5022 −0.0009 0.3703 0.106*
C37 0.1887 (4) −0.0458 (4) −0.0052 (3) 0.1063 (14)
H37A 0.1590 −0.1180 0.0416 0.159*
H37B 0.2233 −0.0650 −0.0641 0.159*
H37C 0.1158 0.0119 −0.0206 0.159*
C38 −0.0057 (3) 0.4495 (3) 0.3365 (3) 0.0771 (10)
H38A 0.0523 0.4502 0.3875 0.116*
H38B −0.0752 0.5102 0.3341 0.116*
H38C 0.0433 0.4662 0.2743 0.116*
Open in a new tab

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
O2A 0.065 (3) 0.046 (3) 0.046 (2) 0.014 (2) −0.0035 (18) −0.0042 (19)
C16A 0.073 (4) 0.081 (5) 0.073 (4) 0.025 (4) 0.012 (3) −0.004 (3)
O2B 0.049 (6) 0.053 (5) 0.056 (5) 0.001 (4) −0.002 (4) −0.011 (4)
C16B 0.080 (11) 0.056 (9) 0.144 (14) 0.010 (8) −0.032 (10) −0.037 (10)
O1 0.0649 (12) 0.0613 (12) 0.0418 (11) 0.0228 (10) −0.0135 (9) −0.0206 (9)
O3 0.0831 (16) 0.0953 (17) 0.0435 (12) 0.0396 (13) −0.0134 (11) −0.0153 (11)
O4 0.0627 (13) 0.0872 (16) 0.0391 (12) 0.0051 (11) 0.0069 (9) −0.0210 (11)
O5 0.0621 (12) 0.0675 (14) 0.0502 (12) 0.0222 (10) −0.0046 (10) −0.0231 (11)
O6 0.0674 (13) 0.0582 (13) 0.0559 (12) 0.0258 (11) −0.0103 (10) −0.0198 (10)
O7 0.0533 (11) 0.0500 (11) 0.0460 (11) 0.0072 (9) −0.0111 (9) −0.0081 (9)
C1 0.0457 (15) 0.0435 (16) 0.0430 (16) 0.0035 (13) −0.0115 (12) −0.0116 (13)
C2 0.0491 (16) 0.0544 (17) 0.0439 (17) 0.0087 (13) −0.0065 (13) −0.0178 (14)
C3 0.0642 (19) 0.064 (2) 0.0463 (18) 0.0266 (16) −0.0108 (14) −0.0185 (15)
C4 0.0522 (17) 0.064 (2) 0.0446 (17) 0.0107 (15) −0.0066 (14) −0.0086 (15)
C5 0.0432 (15) 0.0645 (19) 0.0382 (16) 0.0014 (14) −0.0005 (12) −0.0140 (14)
C6 0.0389 (14) 0.0518 (17) 0.0488 (17) 0.0053 (13) −0.0018 (12) −0.0160 (14)
C7 0.0401 (14) 0.0438 (15) 0.0434 (16) 0.0012 (12) −0.0061 (12) −0.0122 (12)
C8 0.0414 (15) 0.0434 (16) 0.0510 (17) 0.0056 (13) −0.0070 (12) −0.0138 (13)
C9 0.0442 (15) 0.0423 (15) 0.0421 (16) 0.0009 (12) −0.0117 (12) −0.0092 (12)
C10 0.0368 (14) 0.0470 (16) 0.0407 (15) 0.0022 (12) −0.0034 (11) −0.0135 (13)
C11 0.0503 (16) 0.0504 (17) 0.0556 (18) −0.0009 (13) 0.0001 (13) −0.0138 (14)
C12 0.0611 (19) 0.058 (2) 0.085 (3) −0.0021 (15) 0.0023 (17) −0.039 (2)
C13 0.072 (2) 0.088 (3) 0.061 (2) 0.0083 (18) 0.0002 (17) −0.045 (2)
C14 0.072 (2) 0.079 (2) 0.0424 (18) 0.0060 (17) 0.0007 (15) −0.0148 (16)
C15 0.0513 (16) 0.0505 (17) 0.0456 (17) 0.0030 (13) −0.0058 (13) −0.0128 (14)
C17 0.084 (2) 0.124 (3) 0.077 (3) 0.006 (2) −0.018 (2) −0.058 (2)
C18 0.0559 (19) 0.082 (2) 0.066 (2) 0.0076 (17) −0.0229 (16) −0.0194 (17)
O11 0.0491 (10) 0.0463 (11) 0.0465 (11) 0.0086 (9) −0.0069 (8) −0.0144 (9)
O12 0.0581 (12) 0.0522 (11) 0.0445 (11) 0.0141 (9) −0.0080 (9) −0.0037 (9)
O13 0.0733 (13) 0.0622 (13) 0.0485 (12) 0.0293 (11) −0.0090 (10) −0.0188 (10)
O14 0.0605 (13) 0.0839 (15) 0.0515 (13) 0.0176 (11) −0.0041 (10) −0.0227 (11)
O15 0.0735 (15) 0.0762 (15) 0.0498 (12) 0.0290 (11) −0.0159 (11) −0.0095 (11)
O17 0.0416 (10) 0.0568 (13) 0.0751 (14) 0.0130 (9) −0.0060 (9) −0.0251 (11)
O16 0.0634 (13) 0.0673 (14) 0.0600 (13) 0.0266 (11) −0.0135 (10) −0.0120 (11)
C21 0.0351 (14) 0.0437 (16) 0.0577 (18) 0.0010 (12) −0.0053 (13) −0.0165 (14)
C22 0.0413 (14) 0.0433 (15) 0.0439 (16) −0.0026 (12) −0.0056 (12) −0.0112 (13)
C23 0.0447 (15) 0.0409 (15) 0.0426 (16) 0.0045 (12) −0.0101 (12) −0.0066 (12)
C24 0.0456 (16) 0.0443 (16) 0.0504 (18) 0.0052 (13) −0.0058 (13) −0.0079 (13)
C25 0.0519 (17) 0.0545 (18) 0.0427 (17) 0.0053 (14) −0.0034 (13) −0.0121 (14)
C26 0.0464 (16) 0.0540 (17) 0.0452 (17) 0.0060 (14) −0.0107 (13) −0.0075 (13)
C27 0.0398 (14) 0.0418 (15) 0.0468 (16) 0.0014 (12) −0.0069 (12) −0.0078 (12)
C28 0.0404 (15) 0.0457 (16) 0.0547 (18) 0.0037 (13) −0.0122 (13) −0.0088 (14)
C29 0.0354 (14) 0.0453 (16) 0.0653 (19) 0.0042 (12) −0.0078 (13) −0.0200 (14)
C30 0.0413 (15) 0.0505 (17) 0.0528 (18) −0.0055 (13) −0.0010 (13) −0.0194 (14)
C31 0.0537 (18) 0.070 (2) 0.067 (2) 0.0045 (15) −0.0012 (15) −0.0253 (17)
C32 0.061 (2) 0.086 (2) 0.065 (2) −0.0013 (18) 0.0100 (17) −0.0343 (19)
C33 0.070 (2) 0.084 (2) 0.053 (2) −0.0173 (19) 0.0077 (17) −0.0248 (18)
C34 0.075 (2) 0.077 (2) 0.048 (2) 0.0015 (18) −0.0066 (16) −0.0123 (17)
C35 0.0560 (18) 0.061 (2) 0.061 (2) 0.0049 (15) −0.0029 (15) −0.0196 (16)
C36 0.067 (2) 0.067 (2) 0.074 (2) 0.0077 (17) −0.0307 (17) −0.0090 (17)
C37 0.077 (3) 0.174 (4) 0.091 (3) 0.020 (3) −0.019 (2) −0.077 (3)
C38 0.070 (2) 0.050 (2) 0.111 (3) 0.0058 (17) 0.0011 (19) −0.0235 (19)
Open in a new tab

Geometric parameters (Å, °)

O2A—C3 1.404 (5) C18—H18B 0.9599
O2A—C16A 1.416 (7) C18—H18C 0.9599
C16A—H16A 0.9599 O11—C21 1.362 (3)
C16A—H16B 0.9599 O11—C22 1.369 (3)
C16A—H16C 0.9599 O12—C23 1.378 (3)
O2B—C16B 1.425 (13) O12—C36 1.431 (3)
O2B—C3 1.444 (8) O13—C24 1.343 (3)
C16B—H16D 0.9599 O13—H1 0.8200
C16B—H16E 0.9599 O14—C25 1.386 (3)
C16B—H16F 0.9599 O14—C37 1.391 (4)
O1—C1 1.372 (3) O15—C26 1.361 (3)
O1—C2 1.378 (3) O15—H2 0.8200
O3—C4 1.356 (3) O17—C29 1.370 (3)
O3—H3 0.8200 O17—C38 1.435 (3)
O4—C5 1.368 (3) O16—C28 1.262 (3)
O4—C17 1.423 (4) C21—C29 1.363 (4)
O5—C6 1.352 (3) C21—C30 1.473 (4)
O5—H5 0.8200 C22—C23 1.376 (3)
O6—C8 1.243 (3) C22—C27 1.395 (4)
O7—C9 1.373 (3) C23—C24 1.389 (3)
O7—C18 1.423 (3) C24—C25 1.404 (4)
C1—C9 1.346 (3) C25—C26 1.367 (4)
C1—C10 1.473 (3) C26—C27 1.414 (4)
C2—C3 1.381 (4) C27—C28 1.429 (4)
C2—C7 1.387 (3) C28—C29 1.450 (4)
C3—C4 1.390 (4) C30—C35 1.388 (4)
C4—C5 1.398 (4) C30—C31 1.396 (4)
C5—C6 1.379 (4) C31—C32 1.378 (4)
C6—C7 1.404 (3) C31—H31 0.9300
C7—C8 1.456 (4) C32—C33 1.367 (5)
C8—C9 1.441 (3) C32—H32 0.9300
C10—C15 1.386 (4) C33—C34 1.382 (4)
C10—C11 1.390 (4) C33—H33 0.9300
C11—C12 1.378 (4) C34—C35 1.380 (4)
C11—H11 0.9300 C34—H34 0.9300
C12—C13 1.376 (4) C35—H35 0.9300
C12—H12 0.9300 C36—H36A 0.9599
C13—C14 1.372 (4) C36—H36B 0.9599
C13—H13 0.9300 C36—H36C 0.9599
C14—C15 1.375 (4) C37—H37A 0.9599
C14—H14 0.9300 C37—H37B 0.9599
C15—H15 0.9300 C37—H37C 0.9599
C17—H17A 0.9599 C38—H38A 0.9599
C17—H17B 0.9599 C38—H38B 0.9599
C17—H17C 0.9599 C38—H38C 0.9599
C18—H18A 0.9599
C3—O2A—C16A 112.2 (6) H18B—C18—H18C 109.5
C16B—O2B—C3 102.2 (11) C21—O11—C22 121.8 (2)
O2B—C16B—H16D 109.5 C23—O12—C36 114.4 (2)
O2B—C16B—H16E 109.5 C24—O13—H1 109.5
H16D—C16B—H16E 109.5 C25—O14—C37 115.6 (2)
O2B—C16B—H16F 109.5 C26—O15—H2 109.5
H16D—C16B—H16F 109.5 C29—O17—C38 113.8 (2)
H16E—C16B—H16F 109.5 O11—C21—C29 119.9 (2)
C1—O1—C2 119.78 (19) O11—C21—C30 110.4 (2)
C4—O3—H3 109.5 C29—C21—C30 129.7 (2)
C5—O4—C17 113.5 (2) O11—C22—C23 116.5 (2)
C6—O5—H5 109.5 O11—C22—C27 120.7 (2)
C9—O7—C18 113.8 (2) C23—C22—C27 122.8 (2)
C9—C1—O1 121.8 (2) C22—C23—O12 119.7 (2)
C9—C1—C10 127.0 (2) C22—C23—C24 118.1 (2)
O1—C1—C10 111.2 (2) O12—C23—C24 121.9 (2)
O1—C2—C3 116.3 (2) O13—C24—C23 117.6 (2)
O1—C2—C7 121.0 (2) O13—C24—C25 121.8 (2)
C3—C2—C7 122.6 (2) C23—C24—C25 120.6 (2)
C2—C3—C4 117.8 (2) C26—C25—O14 122.8 (2)
C2—C3—O2A 124.0 (3) C26—C25—C24 120.5 (2)
C4—C3—O2A 117.1 (3) O14—C25—C24 116.7 (2)
C2—C3—O2B 119.9 (4) O15—C26—C25 119.7 (2)
C4—C3—O2B 115.5 (4) O15—C26—C27 120.2 (2)
O3—C4—C3 122.4 (2) C25—C26—C27 120.0 (2)
O3—C4—C5 116.5 (2) C22—C27—C26 117.9 (2)
C3—C4—C5 121.2 (3) C22—C27—C28 119.6 (2)
O4—C5—C6 120.0 (2) C26—C27—C28 122.5 (2)
O4—C5—C4 120.2 (2) O16—C28—C27 122.0 (3)
C6—C5—C4 119.8 (2) O16—C28—C29 121.6 (2)
O5—C6—C5 119.3 (2) C27—C28—C29 116.4 (2)
O5—C6—C7 120.7 (2) C21—C29—O17 120.7 (3)
C5—C6—C7 120.0 (2) C21—C29—C28 121.4 (2)
C2—C7—C6 118.6 (2) O17—C29—C28 117.8 (2)
C2—C7—C8 120.3 (2) C35—C30—C31 117.8 (3)
C6—C7—C8 121.1 (2) C35—C30—C21 119.1 (2)
O6—C8—C9 122.6 (2) C31—C30—C21 123.1 (3)
O6—C8—C7 122.4 (2) C32—C31—C30 120.7 (3)
C9—C8—C7 115.0 (2) C32—C31—H31 119.7
C1—C9—O7 119.2 (2) C30—C31—H31 119.7
C1—C9—C8 122.0 (2) C33—C32—C31 120.7 (3)
O7—C9—C8 118.8 (2) C33—C32—H32 119.7
C15—C10—C11 119.5 (2) C31—C32—H32 119.7
C15—C10—C1 120.0 (2) C32—C33—C34 119.7 (3)
C11—C10—C1 120.5 (2) C32—C33—H33 120.1
C12—C11—C10 119.5 (3) C34—C33—H33 120.1
C12—C11—H11 120.2 C35—C34—C33 119.8 (3)
C10—C11—H11 120.2 C35—C34—H34 120.1
C13—C12—C11 120.5 (3) C33—C34—H34 120.1
C13—C12—H12 119.8 C34—C35—C30 121.2 (3)
C11—C12—H12 119.8 C34—C35—H35 119.4
C14—C13—C12 120.1 (3) C30—C35—H35 119.4
C14—C13—H13 120.0 O12—C36—H36A 109.5
C12—C13—H13 120.0 O12—C36—H36B 109.5
C13—C14—C15 120.2 (3) H36A—C36—H36B 109.5
C13—C14—H14 119.9 O12—C36—H36C 109.5
C15—C14—H14 119.9 H36A—C36—H36C 109.5
C14—C15—C10 120.2 (3) H36B—C36—H36C 109.5
C14—C15—H15 119.9 O14—C37—H37A 109.5
C10—C15—H15 119.9 O14—C37—H37B 109.5
O4—C17—H17A 109.5 H37A—C37—H37B 109.5
O4—C17—H17B 109.5 O14—C37—H37C 109.5
H17A—C17—H17B 109.5 H37A—C37—H37C 109.5
O4—C17—H17C 109.5 H37B—C37—H37C 109.5
H17A—C17—H17C 109.5 O17—C38—H38A 109.5
H17B—C17—H17C 109.5 O17—C38—H38B 109.5
O7—C18—H18A 109.5 H38A—C38—H38B 109.5
O7—C18—H18B 109.5 O17—C38—H38C 109.5
H18A—C18—H18B 109.5 H38A—C38—H38C 109.5
O7—C18—H18C 109.5 H38B—C38—H38C 109.5
H18A—C18—H18C 109.5
C2—O1—C1—C9 0.5 (4) C12—C13—C14—C15 1.6 (5)
C2—O1—C1—C10 −179.9 (2) C13—C14—C15—C10 −1.1 (4)
C1—O1—C2—C3 178.1 (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—C4 179.7 (3) C22—O11—C21—C29 −2.0 (4)
C7—C2—C3—C4 0.8 (5) C22—O11—C21—C30 178.8 (2)
O1—C2—C3—O2A 12.1 (5) C21—O11—C22—C23 179.2 (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—O12 2.0 (4)
C7—C2—C3—O2B 150.6 (5) C27—C22—C23—O12 −176.6 (2)
C16A—O2A—C3—C2 −70.4 (7) O11—C22—C23—C24 175.4 (2)
C16A—O2A—C3—C4 121.9 (5) C27—C22—C23—C24 −3.1 (4)
C16A—O2A—C3—O2B 25.1 (6) C36—O12—C23—C22 −113.0 (3)
C16B—O2B—C3—C2 90.0 (11) C36—O12—C23—C24 73.8 (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—O3 178.0 (3) C22—C23—C24—C25 2.7 (4)
O2A—C3—C4—O3 −13.5 (5) O12—C23—C24—C25 176.0 (2)
O2B—C3—C4—O3 26.8 (6) C37—O14—C25—C26 −70.2 (4)
C2—C3—C4—C5 −1.3 (5) C37—O14—C25—C24 111.0 (3)
O2A—C3—C4—C5 167.2 (3) O13—C24—C25—C26 178.8 (3)
O2B—C3—C4—C5 −152.5 (5) C23—C24—C25—C26 −1.2 (4)
C17—O4—C5—C6 92.7 (3) O13—C24—C25—O14 −2.4 (4)
C17—O4—C5—C4 −87.7 (3) C23—C24—C25—O14 177.6 (2)
O3—C4—C5—O4 2.6 (4) O14—C25—C26—O15 1.3 (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—C6 1.6 (4) C24—C25—C26—C27 0.0 (4)
O4—C5—C6—O5 −1.4 (4) O11—C22—C27—C26 −176.5 (2)
C4—C5—C6—O5 178.9 (2) C23—C22—C27—C26 2.0 (4)
O4—C5—C6—C7 178.4 (2) O11—C22—C27—C28 2.6 (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—C22 179.6 (2)
C3—C2—C7—C6 −0.5 (4) C25—C26—C27—C22 −0.3 (4)
O1—C2—C7—C8 3.2 (4) O15—C26—C27—C28 0.5 (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—C2 0.7 (4) C26—C27—C28—O16 0.0 (4)
O5—C6—C7—C8 −2.1 (4) C22—C27—C28—C29 0.8 (4)
C5—C6—C7—C8 178.1 (2) C26—C27—C28—C29 179.9 (2)
C2—C7—C8—O6 179.1 (2) O11—C21—C29—O17 −179.2 (2)
C6—C7—C8—O6 1.7 (4) C30—C21—C29—O17 −0.1 (4)
C2—C7—C8—C9 −1.1 (4) O11—C21—C29—C28 5.6 (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—C21 101.0 (3)
C10—C1—C9—O7 2.4 (4) C38—O17—C29—C28 −83.6 (3)
O1—C1—C9—C8 1.6 (4) O16—C28—C29—C21 175.0 (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—C8 79.7 (3) C27—C28—C29—O17 179.8 (2)
O6—C8—C9—C1 178.5 (3) O11—C21—C30—C35 7.0 (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—O7 178.4 (2) C29—C21—C30—C31 9.5 (4)
C9—C1—C10—C15 −42.8 (4) C35—C30—C31—C32 1.5 (4)
O1—C1—C10—C15 137.6 (2) C21—C30—C31—C32 179.9 (3)
C9—C1—C10—C11 138.3 (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—C12 1.8 (4) C32—C33—C34—C35 0.2 (5)
C1—C10—C11—C12 −179.3 (2) C33—C34—C35—C30 0.6 (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)
Open in a new tab

Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
O3—H3···O16i 0.82 2.06 2.806 (3) 152
O3—H3···O2A 0.82 2.36 2.772 (5) 112
O3—H3···O2B 0.82 2.37 2.799 (9) 114
O5—H5···O6 0.82 1.86 2.586 (3) 146
O13—H1···O5ii 0.82 2.05 2.825 (3) 158
O13—H1···O14 0.82 2.29 2.736 (3) 115
O15—H2···O16 0.82 1.88 2.600 (3) 147
Open in a new tab

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).

References

  1. Ali, E., Bagchi, D. & Pakrashi, S. C. (1979). Phytochemistry, 18, 356–357.
  2. Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Chinese Materia Medica (2007). Chinese Materia Medica, Vol. 21, p. 643. Shanghai Science Press.
  4. Cubukcu, B. & Bingol, S. (1984). Plant Med. Phytother 18, 28–35.
  5. Guerreiro, E., Kavka, J. & Giordano, O. S. (1982). Phytochemistry, 21, 2601–2602.
  6. Horie, T., Kawamura, Y., Yamamoto, H. & Yamashita, K. (1995). Chem. Pharm. Bull. 43, 2054–2063.
  7. Jakupovic, J., Zdero, C., Grenz, M., Tsichritzis, F., Lehmann, L., Hashemi-Nejad, S. & Bohlmann, F. (1989). Phytochemistry, 28, 1119–1131.
  8. Lavault, M. & Richomme, P. (2004). Chem. Nat. Comp., 40, 118–121.
  9. Mericli, A. H., Damadtan, B. & Cubukcu, B. (1986). Sci. Pharm. 54, 363–365.
  10. Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
  11. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]
  12. Tomas-Lorente, F., Iniesta-Sanmrtin, E., Tomas-Barberan, F. A., Trowitzsch-Kienast, W. & Wray, V. (1989). Phytochemistry, 28, 1613–1615.
  13. Torrenegra, R. D., Escarria, S., Raffelsberger, B. & Achenbach, H. (1980). Phytochemistry, 19, 2795–2796.
  14. Urzua, A., Torres, R., Bueno, C. & Mendoza, L. (1995). Biochem. Syst. Ecol 23, 459.
  15. Wollenweber, E., Fischer, R., Doerr, M., Irvine, K., Pereira, C. & Stevens, J. F. (2008). J. Biosci. 63, 731–739. [DOI] [PubMed]
  16. Wollenweber, E., Fritz, H., Henrich, B., Jakupovic, J., Schilling, G. & Roitman, J. N. (1993). J. Biosci. 48, 420–424.

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

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

e-65-o3276-sup1.cif (30.6KB, cif)

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

e-65-o3276-Isup2.hkl (273.7KB, hkl)

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

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography

RESOURCES