PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o202.
Published online 2007 December 6. doi:  10.1107/S1600536807063763
PMCID: PMC2915264

7-(Hydroxy­meth­yl)-2-(1-hydr­oxy-1-methyl­ethyl)-4-meth­oxy-2,3-dihydro-5H-furo[3,2-g]chromen-5-one methanol hemisolvate

Abstract

The title compound (cimifugin), C16H18O6·0.5CH3OH, was isolated from the rhizome of Actaea asiatica Hara. The asymmetric unit contains two independent mol­ecules and a solvent methanol mol­ecule. The five-numbered ring adopts an envelope conformation in each molecule. Intra- and inter­molecular O—H(...)O hydrogen bonds stabilize the crystal structure.

Related literature

For related literature, see: Kusano et al. (1998 [triangle], 1999 [triangle]); Wan (1990 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-0o202-scheme1.jpg

Experimental

Crystal data

  • C16H18O6·0.5CH4O
  • M r = 322.33
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o202-efi1.jpg
  • a = 9.4092 (14) Å
  • b = 13.4176 (19) Å
  • c = 12.6903 (18) Å
  • β = 91.600 (2)°
  • V = 1601.5 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 294 (2) K
  • 0.30 × 0.28 × 0.24 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 1997 [triangle]) T min = 0.956, T max = 0.976
  • 9210 measured reflections
  • 3408 independent reflections
  • 2556 reflections with I > 2σ(I)
  • R int = 0.027

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.108
  • S = 1.03
  • 3408 reflections
  • 437 parameters
  • 12 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.17 e Å−3
  • Δρmin = −0.21 e Å−3

Data collection: SMART (Bruker, 1997 [triangle]); cell refinement: SAINT (Bruker, 1997 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL (Bruker, 1997 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536807063763/gg2062sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807063763/gg2062Isup2.hkl

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

Acknowledgments

This work was supported by the fund of the SRTP of Henan University of Science and Technology.

supplementary crystallographic information

Comment

Actaea asiatica Hara (Ranunculaceae) is widely distributed in the southwest and northwest of the People's Republic of China. As a Chinesa folk medicine, its rhizome is used to treat headache, sore throat, measles, pertussis, prolapse of uterus (Wan, 1990). Previous phytochemical investigations have reported in the isolation of cimiaceroside A and 26-deoxycimicifugoside from this plant (Kusano et al., 1998, 1999). To investigate the bioactive natural products from A. asiatica, chemical studies of the rhizome of the plant were undertaken by screening using immunopotent tests in vitro, we obtained a compund, viz. cimifugin, from the petroleum ether extract. The structure of cimifugin was elucidated by extensive spectroscopic analysis, including two-dimensional NMR spectroscopy, and established unequivocally by single-crystal X-ray diffraction analysis.

The molecular structure of (I) and the atom-numbering scheme are shown in Fig. 1. The asymmetric unit of (I) contains two independent molecules and a methanol of solvation. The molecule is composed of a fused five-numbered ring and two fused six-numbered viz. A(C1–C3/C11/O2), B(C3–C5/C9–C11) and C(C5–C9/O4). In the two molecules, two fused six-numbered (B and C) are almost planar with the r.m.s. deviations of 0.0129 (4) and 1.0103 (4) Å, respectively, while ring C does not deviate form the chromone plane. The O5—C6—C5 and C7—C6—C5 angles are 123.3 (4)° and 115.8 (3)°, respectively, which indicates that carbonyl C6 atom slightly deviates from the ideal value of 120°. The similar deviation is also observed for the C22 with the angles of O11—C22—C21 [124.4 (3)°] and C23—C22—C21 [115.2 (3)°].

The hydroxy groups are attached at atoms C12, C16, C28 and C32. The methoxy group located at atoms C4 and C20. The interactions of intermolecular and intramolecular hydrogen bonds are formed between the hydroxy and carbonyl groups, which stablize the crystal structure.

Experimental

The rhizomes of Phlomis umbrosa turcz was collected in Jianshi county, Hubei province, China, January 2006. The plants were identified as Actaea asiatica Hara by Professor Ding-rong Wan, College of Life Science, South-Central University for Nationalities. A voucher specimen (No. D20050115) was deposited in the laboratory of Natural products, Tinjing Medical University. The rhizomes of Actaea asiatica Hara was dried at room temperature in the dark. The material (4.3 kg) was extracted three times with 95% ethanol under reflux. The 95% ethanol extract (500 g) was suspended in water, and then extracted with petroleum ether, ethyl acetate and n-butanol successively. The ethyl acetate layer (80 g) was absorbed on to silica gel (150 g) and chromatographed on a silica gel (1000 g) column eluted with petroleum ether–EtOAc with the increased polarity to give 25 fractions. Fraction 8 was further separated on Toyopear HW-40, pre. HPLC-ODS to afford 200 mg of cimifugin. 13C NMR (300 MHz, CD3OD, p.p.m.): 92.7, 28.8, 118.4, 167.1, 112.3, 179.7, 109.3, 168.7, 157.0, 94.5, 161.1, 72.3, 25.4, 25.5, 61.0, 61.2. Crystals suitable for X-ray structure analysis were obtained by slow evaporation from methanol at room temperature.

Refinement

H atoms of the hydroxy group were located in a difference density map and the atomic coordinates allowed to refine freely. Other H atoms were positioned geometrically and refined as riding with C—H = 0.95–0.98 Å). For the CH and CH2 groups, Uiso(H) values are set equal to 1.2Ueq(carrier atom) and for the methyl groups they are set equal to 1.5Ueq(carrier atom). The absolute configuration could not be established because of the absence of significant anomalous effects. Friedel pairs were merged for the final cycles of refinement.

Figures

Fig. 1.
View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen atoms have been omitted for clarity.

Crystal data

C16H18O6·0.5CH4OF000 = 684
Mr = 322.33Dx = 1.337 Mg m3
Monoclinic, P21Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ybCell parameters from 3898 reflections
a = 9.4092 (14) Åθ = 2.6–25.4º
b = 13.4176 (19) ŵ = 0.10 mm1
c = 12.6903 (18) ÅT = 294 (2) K
β = 91.600 (2)ºPlate, colourless
V = 1601.5 (4) Å30.30 × 0.28 × 0.24 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer3408 independent reflections
Radiation source: fine-focus sealed tube2556 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.027
T = 294(2) Kθmax = 26.4º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Bruker, 1997)h = −11→11
Tmin = 0.956, Tmax = 0.976k = −16→9
9210 measured reflectionsl = −15→15

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.108  w = 1/[σ2(Fo2) + (0.0592P)2 + 0.2147P] where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.003
3408 reflectionsΔρmax = 0.17 e Å3
437 parametersΔρmin = −0.21 e Å3
12 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

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 (Å2)

xyzUiso*/Ueq
O10.8781 (3)0.6603 (2)0.4785 (2)0.0674 (7)
H10.820 (5)0.621 (3)0.508 (4)0.101*
O20.9188 (3)0.65092 (18)0.70280 (17)0.0545 (6)
O30.7862 (3)0.97796 (18)0.7545 (2)0.0663 (7)
O40.6245 (3)0.71772 (16)0.98859 (17)0.0499 (6)
O50.6128 (4)1.0136 (2)0.9273 (3)0.1017 (12)
O60.4013 (3)0.7906 (2)1.1992 (2)0.0779 (9)
H60.475 (4)0.799 (5)1.239 (4)0.117*
O70.1990 (3)0.9270 (2)1.1264 (2)0.0634 (7)
H70.254 (5)0.878 (3)1.147 (4)0.095*
O80.1715 (3)0.7605 (2)0.98115 (17)0.0566 (6)
O90.3011 (3)0.93880 (18)0.67958 (17)0.0550 (6)
O100.4679 (2)0.60625 (15)0.73882 (16)0.0445 (5)
O110.4630 (3)0.84518 (19)0.54207 (17)0.0570 (6)
O120.6907 (3)0.5091 (2)0.53907 (19)0.0619 (7)
H120.642 (5)0.467 (3)0.502 (3)0.093*
C11.0036 (4)0.7143 (3)0.6349 (3)0.0518 (8)
H1A1.09940.72000.66680.062*
C20.9341 (4)0.8170 (3)0.6371 (3)0.0553 (9)
H2A1.00470.86940.64350.066*
H2B0.87520.82840.57430.066*
C30.8461 (4)0.8111 (3)0.7335 (3)0.0463 (8)
C40.7736 (4)0.8812 (2)0.7866 (3)0.0468 (8)
C50.6943 (3)0.8538 (2)0.8758 (3)0.0445 (7)
C60.6171 (4)0.9232 (3)0.9427 (3)0.0554 (9)
C70.5464 (4)0.8794 (3)1.0296 (3)0.0541 (9)
H7A0.49590.92041.07430.065*
C80.5506 (4)0.7821 (3)1.0485 (3)0.0505 (8)
C90.6955 (3)0.7524 (2)0.9032 (2)0.0430 (7)
C100.7682 (4)0.6792 (2)0.8496 (3)0.0460 (8)
H100.76620.61260.86960.055*
C110.8426 (4)0.7116 (2)0.7658 (2)0.0447 (8)
C121.0158 (4)0.6656 (3)0.5284 (3)0.0581 (9)
C131.0790 (6)0.5624 (4)0.5394 (4)0.0854 (14)
H13A1.01470.52030.57650.128*
H13B1.16800.56620.57810.128*
H13C1.09430.53510.47070.128*
C141.1047 (5)0.7311 (4)0.4586 (3)0.0798 (13)
H14A1.11280.70030.39080.120*
H14B1.19760.73950.49040.120*
H14C1.05980.79500.45040.120*
C150.6701 (5)1.0182 (4)0.6989 (4)0.0815 (13)
H15A0.66730.99230.62840.122*
H15B0.67891.08940.69670.122*
H15C0.58411.00050.73330.122*
C160.4762 (5)0.7266 (3)1.1319 (3)0.0698 (11)
H16A0.41000.67981.09900.084*
H16B0.54530.68861.17340.084*
C170.0789 (4)0.8478 (3)0.9780 (3)0.0529 (8)
H17−0.01560.82720.95180.063*
C180.1425 (4)0.9172 (3)0.8981 (3)0.0535 (9)
H18A0.06910.94760.85360.064*
H18B0.19840.96920.93250.064*
C190.2351 (3)0.8488 (2)0.8353 (2)0.0414 (7)
C200.3053 (3)0.8572 (2)0.7426 (2)0.0409 (7)
C210.3860 (3)0.7750 (2)0.7045 (2)0.0373 (6)
C220.4621 (3)0.7746 (3)0.6053 (2)0.0420 (7)
C230.5373 (4)0.6851 (3)0.5837 (2)0.0459 (8)
H230.58690.68130.52140.055*
C240.5404 (3)0.6068 (2)0.6479 (2)0.0425 (7)
C250.3925 (3)0.6894 (2)0.7668 (2)0.0388 (7)
C260.3224 (4)0.6792 (3)0.8611 (2)0.0453 (8)
H260.32720.62120.90100.054*
C270.2462 (3)0.7599 (3)0.8910 (2)0.0452 (8)
C280.0656 (4)0.8878 (3)1.0900 (3)0.0597 (10)
C29−0.0371 (4)0.9744 (4)1.0879 (4)0.0836 (15)
H29A−0.03741.00531.15610.125*
H29B−0.13090.95081.06970.125*
H29C−0.00831.02231.03640.125*
C300.0158 (6)0.8050 (4)1.1621 (3)0.0948 (17)
H30A0.08480.75231.16400.142*
H30B−0.07380.77951.13580.142*
H30C0.00480.83091.23190.142*
C310.2736 (5)1.0340 (3)0.7232 (3)0.0749 (12)
H31A0.17291.04290.72920.112*
H31B0.31051.08480.67820.112*
H31C0.31881.03880.79180.112*
C320.6206 (4)0.5121 (3)0.6356 (3)0.0550 (9)
H32A0.69000.50560.69320.066*
H32B0.55540.45630.63920.066*
O130.5854 (4)0.7999 (3)0.3575 (2)0.0998 (12)
H130.569 (7)0.802 (6)0.432 (2)0.150*
C330.7073 (6)0.8399 (6)0.3440 (5)0.125 (2)
H33A0.73790.87370.40730.187*
H33B0.70040.88680.28700.187*
H33C0.77500.78910.32740.187*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0728 (18)0.077 (2)0.0523 (14)−0.0222 (15)−0.0001 (12)−0.0111 (13)
O20.0746 (16)0.0410 (13)0.0481 (12)0.0016 (12)0.0068 (11)−0.0057 (11)
O30.0728 (17)0.0358 (13)0.0905 (19)−0.0054 (13)0.0057 (14)0.0072 (13)
O40.0659 (15)0.0334 (11)0.0506 (12)0.0051 (11)0.0029 (11)−0.0036 (10)
O50.178 (4)0.0319 (15)0.098 (2)0.0235 (19)0.049 (2)0.0063 (15)
O60.105 (2)0.0615 (19)0.0684 (18)0.0135 (18)0.0215 (16)−0.0086 (15)
O70.0598 (16)0.0650 (17)0.0650 (15)0.0035 (13)−0.0056 (12)−0.0216 (13)
O80.0731 (15)0.0553 (14)0.0425 (12)−0.0063 (13)0.0191 (11)−0.0037 (11)
O90.0782 (16)0.0441 (13)0.0431 (12)0.0104 (12)0.0091 (11)0.0063 (10)
O100.0612 (14)0.0357 (12)0.0371 (11)−0.0021 (10)0.0088 (10)−0.0013 (9)
O110.0722 (16)0.0570 (15)0.0426 (12)0.0135 (13)0.0156 (11)0.0146 (11)
O120.0786 (18)0.0524 (15)0.0559 (15)−0.0120 (13)0.0216 (12)−0.0181 (12)
C10.053 (2)0.049 (2)0.0533 (19)−0.0027 (16)−0.0018 (16)−0.0045 (16)
C20.064 (2)0.048 (2)0.054 (2)−0.0061 (18)0.0000 (17)−0.0041 (16)
C30.0536 (19)0.0385 (17)0.0464 (17)−0.0031 (15)−0.0063 (15)−0.0035 (14)
C40.0505 (18)0.0314 (17)0.0579 (19)−0.0038 (14)−0.0081 (16)−0.0023 (14)
C50.0491 (18)0.0315 (16)0.0524 (18)0.0021 (14)−0.0073 (15)−0.0053 (14)
C60.074 (2)0.0324 (19)0.059 (2)0.0060 (17)−0.0028 (18)−0.0057 (16)
C70.065 (2)0.0394 (19)0.058 (2)0.0078 (16)0.0020 (17)−0.0101 (16)
C80.063 (2)0.0402 (19)0.0480 (17)0.0059 (16)−0.0013 (16)−0.0070 (15)
C90.0505 (18)0.0342 (17)0.0438 (16)−0.0018 (14)−0.0078 (14)−0.0030 (14)
C100.060 (2)0.0303 (15)0.0475 (17)0.0044 (15)−0.0068 (15)−0.0023 (14)
C110.055 (2)0.0351 (16)0.0434 (17)0.0049 (15)−0.0076 (14)−0.0068 (14)
C120.058 (2)0.060 (2)0.057 (2)−0.0059 (19)0.0067 (17)−0.0110 (18)
C130.103 (4)0.069 (3)0.085 (3)0.012 (3)0.021 (3)−0.018 (3)
C140.071 (3)0.095 (4)0.073 (3)−0.013 (3)0.016 (2)−0.009 (3)
C150.087 (3)0.061 (3)0.097 (3)0.012 (2)0.018 (3)0.025 (2)
C160.108 (3)0.048 (2)0.054 (2)0.007 (2)0.016 (2)−0.0045 (18)
C170.0483 (19)0.060 (2)0.0508 (18)−0.0060 (17)0.0090 (15)−0.0129 (17)
C180.058 (2)0.051 (2)0.0510 (19)0.0027 (17)0.0047 (16)−0.0082 (16)
C190.0442 (17)0.0448 (18)0.0354 (15)−0.0032 (14)0.0028 (13)−0.0050 (14)
C200.0435 (17)0.0416 (17)0.0372 (15)−0.0011 (14)−0.0026 (13)−0.0022 (13)
C210.0388 (15)0.0413 (17)0.0317 (13)−0.0056 (13)−0.0012 (11)−0.0013 (13)
C220.0420 (17)0.0484 (19)0.0354 (15)−0.0031 (15)0.0013 (13)0.0025 (14)
C230.0535 (19)0.0487 (19)0.0360 (15)−0.0007 (16)0.0089 (14)−0.0018 (14)
C240.0480 (18)0.0421 (17)0.0375 (16)−0.0053 (15)0.0034 (13)−0.0057 (14)
C250.0430 (17)0.0380 (17)0.0354 (15)−0.0053 (14)0.0010 (13)−0.0059 (13)
C260.060 (2)0.0402 (17)0.0364 (15)−0.0103 (16)0.0064 (14)−0.0016 (13)
C270.0515 (19)0.0509 (19)0.0335 (15)−0.0111 (16)0.0074 (13)−0.0092 (15)
C280.054 (2)0.077 (3)0.0486 (18)−0.0041 (19)0.0108 (16)−0.0169 (19)
C290.065 (2)0.108 (4)0.078 (3)0.016 (3)0.008 (2)−0.040 (3)
C300.110 (4)0.120 (5)0.056 (2)−0.026 (3)0.033 (2)−0.009 (3)
C310.117 (4)0.049 (2)0.059 (2)0.004 (2)0.006 (2)0.0002 (19)
C320.078 (2)0.0362 (17)0.0510 (19)−0.0038 (17)0.0131 (17)−0.0068 (15)
O130.126 (3)0.113 (3)0.0614 (18)0.022 (2)0.0245 (19)0.0038 (19)
C330.081 (3)0.163 (6)0.130 (4)0.015 (4)−0.012 (3)0.014 (5)

Geometric parameters (Å, °)

O1—C121.428 (5)C14—H14A0.9600
O1—H10.85 (3)C14—H14B0.9600
O2—C111.359 (4)C14—H14C0.9600
O2—C11.464 (4)C15—H15A0.9600
O3—C41.367 (4)C15—H15B0.9600
O3—C151.393 (5)C15—H15C0.9600
O4—C81.356 (4)C16—H16A0.9700
O4—C91.370 (4)C16—H16B0.9700
O5—C61.229 (4)C17—C181.512 (5)
O6—C161.415 (5)C17—C281.527 (5)
O6—H60.85 (3)C17—H170.9800
O7—C281.426 (5)C18—C191.509 (4)
O7—H70.87 (3)C18—H18A0.9700
O8—C271.359 (4)C18—H18B0.9700
O8—C171.459 (5)C19—C201.369 (4)
O9—C201.356 (4)C19—C271.389 (5)
O9—C311.419 (5)C20—C211.431 (4)
O10—C241.356 (4)C21—C251.395 (4)
O10—C251.375 (4)C21—C221.465 (4)
O11—C221.242 (4)C22—C231.424 (5)
O12—C321.409 (4)C23—C241.330 (4)
O12—H120.85 (3)C23—H230.9300
C1—C121.508 (5)C24—C321.488 (5)
C1—C21.526 (5)C25—C261.388 (4)
C1—H1A0.9800C26—C271.358 (5)
C2—C31.498 (5)C26—H260.9300
C2—H2A0.9700C28—C291.511 (6)
C2—H2B0.9700C28—C301.522 (6)
C3—C41.354 (5)C29—H29A0.9600
C3—C111.397 (5)C29—H29B0.9600
C4—C51.421 (5)C29—H29C0.9600
C5—C91.403 (4)C30—H30A0.9600
C5—C61.467 (5)C30—H30B0.9600
C6—C71.430 (5)C30—H30C0.9600
C7—C81.328 (5)C31—H31A0.9600
C7—H7A0.9300C31—H31B0.9600
C8—C161.485 (5)C31—H31C0.9600
C9—C101.386 (4)C32—H32A0.9700
C10—C111.361 (5)C32—H32B0.9700
C10—H100.9300O13—C331.283 (7)
C12—C131.512 (6)O13—H130.96 (3)
C12—C141.515 (6)C33—H33A0.9600
C13—H13A0.9600C33—H33B0.9600
C13—H13B0.9600C33—H33C0.9600
C13—H13C0.9600
C12—O1—H1115 (4)H16A—C16—H16B107.9
C11—O2—C1107.7 (3)O8—C17—C18105.4 (3)
C4—O3—C15116.4 (3)O8—C17—C28108.7 (3)
C8—O4—C9119.7 (3)C18—C17—C28116.8 (3)
C16—O6—H691 (4)O8—C17—H17108.5
C28—O7—H7109 (4)C18—C17—H17108.5
C27—O8—C17107.7 (3)C28—C17—H17108.5
C20—O9—C31119.9 (3)C19—C18—C17103.0 (3)
C24—O10—C25119.4 (2)C19—C18—H18A111.2
C32—O12—H12104 (3)C17—C18—H18A111.2
O2—C1—C12109.4 (3)C19—C18—H18B111.2
O2—C1—C2105.8 (3)C17—C18—H18B111.2
C12—C1—C2116.8 (3)H18A—C18—H18B109.1
O2—C1—H1A108.2C20—C19—C27118.5 (3)
C12—C1—H1A108.2C20—C19—C18134.7 (3)
C2—C1—H1A108.2C27—C19—C18106.8 (3)
C3—C2—C1102.4 (3)O9—C20—C19124.5 (3)
C3—C2—H2A111.3O9—C20—C21115.4 (2)
C1—C2—H2A111.3C19—C20—C21120.0 (3)
C3—C2—H2B111.3C25—C21—C20117.2 (2)
C1—C2—H2B111.3C25—C21—C22118.0 (3)
H2A—C2—H2B109.2C20—C21—C22124.8 (3)
C4—C3—C11120.1 (3)O11—C22—C23120.4 (3)
C4—C3—C2131.9 (3)O11—C22—C21124.4 (3)
C11—C3—C2107.9 (3)C23—C22—C21115.2 (3)
C3—C4—O3117.6 (3)C24—C23—C22123.4 (3)
C3—C4—C5120.0 (3)C24—C23—H23118.3
O3—C4—C5122.4 (3)C22—C23—H23118.3
C9—C5—C4116.6 (3)C23—C24—O10121.6 (3)
C9—C5—C6118.2 (3)C23—C24—C32127.8 (3)
C4—C5—C6125.2 (3)O10—C24—C32110.7 (3)
O5—C6—C7120.9 (4)O10—C25—C26113.8 (3)
O5—C6—C5123.3 (4)O10—C25—C21122.4 (2)
C7—C6—C5115.8 (3)C26—C25—C21123.7 (3)
C8—C7—C6122.1 (3)C27—C26—C25115.5 (3)
C8—C7—H7A119.0C27—C26—H26122.3
C6—C7—H7A119.0C25—C26—H26122.3
C7—C8—O4122.6 (3)C26—C27—O8122.0 (3)
C7—C8—C16127.6 (3)C26—C27—C19125.1 (3)
O4—C8—C16109.8 (3)O8—C27—C19112.9 (3)
O4—C9—C10113.9 (3)O7—C28—C29106.2 (3)
O4—C9—C5121.7 (3)O7—C28—C30110.9 (3)
C10—C9—C5124.4 (3)C29—C28—C30111.4 (4)
C11—C10—C9115.4 (3)O7—C28—C17109.7 (3)
C11—C10—H10122.3C29—C28—C17108.8 (3)
C9—C10—H10122.3C30—C28—C17109.7 (3)
O2—C11—C10124.1 (3)C28—C29—H29A109.5
O2—C11—C3112.5 (3)C28—C29—H29B109.5
C10—C11—C3123.4 (3)H29A—C29—H29B109.5
O1—C12—C1109.1 (3)C28—C29—H29C109.5
O1—C12—C13110.2 (4)H29A—C29—H29C109.5
C1—C12—C13110.7 (3)H29B—C29—H29C109.5
O1—C12—C14106.2 (3)C28—C30—H30A109.5
C1—C12—C14109.2 (3)C28—C30—H30B109.5
C13—C12—C14111.3 (4)H30A—C30—H30B109.5
C12—C13—H13A109.5C28—C30—H30C109.5
C12—C13—H13B109.5H30A—C30—H30C109.5
H13A—C13—H13B109.5H30B—C30—H30C109.5
C12—C13—H13C109.5O9—C31—H31A109.5
H13A—C13—H13C109.5O9—C31—H31B109.5
H13B—C13—H13C109.5H31A—C31—H31B109.5
C12—C14—H14A109.5O9—C31—H31C109.5
C12—C14—H14B109.5H31A—C31—H31C109.5
H14A—C14—H14B109.5H31B—C31—H31C109.5
C12—C14—H14C109.5O12—C32—C24111.5 (3)
H14A—C14—H14C109.5O12—C32—H32A109.3
H14B—C14—H14C109.5C24—C32—H32A109.3
O3—C15—H15A109.5O12—C32—H32B109.3
O3—C15—H15B109.5C24—C32—H32B109.3
H15A—C15—H15B109.5H32A—C32—H32B108.0
O3—C15—H15C109.5C33—O13—H13107 (4)
H15A—C15—H15C109.5O13—C33—H33A109.5
H15B—C15—H15C109.5O13—C33—H33B109.5
O6—C16—C8112.2 (3)H33A—C33—H33B109.5
O6—C16—H16A109.2O13—C33—H33C109.5
C8—C16—H16A109.2H33A—C33—H33C109.5
O6—C16—H16B109.2H33B—C33—H33C109.5
C8—C16—H16B109.2
C15—O3—C4—C3105.4 (4)C7—C8—C16—O6−3.9 (6)
C15—O3—C4—C5−78.1 (4)O4—C8—C16—O6177.9 (3)
C31—O9—C20—C1926.1 (5)C27—O8—C17—C18−19.7 (3)
C31—O9—C20—C21−156.1 (3)C27—O8—C17—C28−145.7 (3)
C11—O2—C1—C12−145.4 (3)O8—C17—C18—C1919.3 (3)
C11—O2—C1—C2−18.8 (3)C28—C17—C18—C19140.1 (3)
O2—C1—C2—C318.2 (3)C17—C18—C19—C20168.0 (3)
C12—C1—C2—C3140.2 (3)C17—C18—C19—C27−12.7 (3)
C1—C2—C3—C4170.2 (4)C27—C19—C20—O9178.6 (3)
C1—C2—C3—C11−11.7 (4)C18—C19—C20—O9−2.2 (6)
C11—C3—C4—O3177.0 (3)C27—C19—C20—C210.9 (4)
C2—C3—C4—O3−5.1 (6)C18—C19—C20—C21−179.9 (3)
C11—C3—C4—C50.3 (5)O9—C20—C21—C25−179.7 (3)
C2—C3—C4—C5178.2 (3)C19—C20—C21—C25−1.9 (4)
C3—C4—C5—C9−0.6 (4)O9—C20—C21—C220.4 (4)
O3—C4—C5—C9−177.0 (3)C19—C20—C21—C22178.3 (3)
C3—C4—C5—C6177.0 (3)C25—C21—C22—O11178.8 (3)
O3—C4—C5—C60.5 (5)C20—C21—C22—O11−1.4 (5)
C9—C5—C6—O5178.0 (4)C25—C21—C22—C23−0.7 (4)
C4—C5—C6—O50.5 (6)C20—C21—C22—C23179.1 (3)
C9—C5—C6—C7−1.5 (5)O11—C22—C23—C24−179.9 (3)
C4—C5—C6—C7−178.9 (3)C21—C22—C23—C24−0.3 (5)
O5—C6—C7—C8−179.3 (4)C22—C23—C24—O101.6 (5)
C5—C6—C7—C80.1 (5)C22—C23—C24—C32−176.9 (3)
C6—C7—C8—O41.5 (6)C25—O10—C24—C23−1.8 (4)
C6—C7—C8—C16−176.4 (4)C25—O10—C24—C32176.9 (3)
C9—O4—C8—C7−1.7 (5)C24—O10—C25—C26179.6 (3)
C9—O4—C8—C16176.6 (3)C24—O10—C25—C210.7 (4)
C8—O4—C9—C10179.2 (3)C20—C21—C25—O10−179.3 (3)
C8—O4—C9—C50.2 (4)C22—C21—C25—O100.5 (4)
C4—C5—C9—O4179.1 (3)C20—C21—C25—C261.9 (4)
C6—C5—C9—O41.4 (5)C22—C21—C25—C26−178.3 (3)
C4—C5—C9—C100.2 (5)O10—C25—C26—C27−179.7 (3)
C6—C5—C9—C10−177.5 (3)C21—C25—C26—C27−0.8 (4)
O4—C9—C10—C11−178.5 (3)C25—C26—C27—O8179.7 (3)
C5—C9—C10—C110.5 (5)C25—C26—C27—C19−0.3 (5)
C1—O2—C11—C10−169.7 (3)C17—O8—C27—C26−167.8 (3)
C1—O2—C11—C311.7 (4)C17—O8—C27—C1912.1 (3)
C9—C10—C11—O2−179.1 (3)C20—C19—C27—C260.2 (5)
C9—C10—C11—C3−0.7 (5)C18—C19—C27—C26−179.2 (3)
C4—C3—C11—O2178.9 (3)C20—C19—C27—O8−179.7 (3)
C2—C3—C11—O20.5 (4)C18—C19—C27—O80.9 (4)
C4—C3—C11—C100.3 (5)O8—C17—C28—O767.5 (4)
C2—C3—C11—C10−178.0 (3)C18—C17—C28—O7−51.5 (4)
O2—C1—C12—O164.8 (4)O8—C17—C28—C29−176.7 (3)
C2—C1—C12—O1−55.4 (4)C18—C17—C28—C2964.3 (4)
O2—C1—C12—C13−56.6 (4)O8—C17—C28—C30−54.6 (4)
C2—C1—C12—C13−176.8 (4)C18—C17—C28—C30−173.6 (4)
O2—C1—C12—C14−179.6 (3)C23—C24—C32—O12−4.5 (5)
C2—C1—C12—C1460.3 (4)O10—C24—C32—O12176.9 (3)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O12—H12···O9i0.85 (3)2.41 (4)2.934 (3)120 (4)
O12—H12···O11i0.85 (3)1.99 (3)2.812 (3)162 (5)
O6—H6···O13ii0.85 (3)1.80 (3)2.618 (5)159 (6)
O13—H13···O110.96 (3)1.83 (4)2.708 (4)150 (6)
O7—H7···O60.87 (3)1.92 (3)2.779 (4)169 (5)
O1—H1···O120.85 (3)1.98 (3)2.809 (4)164 (5)

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: GG2062).

References

  • Bruker (1997). SMART (Version 5.611), SAINT (Version 6.0), SADABS (Version 2.03) and SHELXTL (Version 5.10). Bruker AXS Inc., Madison, Wisconsin, USA.
  • Kusano, A., Takahira, M., Shibano, M., Miyase, T. & Kusano, G. (1999). Chem. Pharm. Bull.47, 511–516.
  • Kusano, A., Takahira, M., Shibano, M., Miyase, T., Okuyama, T. & Kusano, G. (1998). Heterocycles, 48, 1003–1013.
  • Sheldrick, G. M. (1997). SHELXS97and SHELXL97 University of Göttingen, Germany.
  • Wan, D. R. (1990). J. Chin. Med. Mater.13, 3–15.

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