organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

An ent-kaurane diterpenoid from Isodon japonica var. glaucocalyx

aSchool of Pharmacy, Xinxiang Medical University, Xinxiang, Henan 453003, People's Republic of China, and bDepartment of Science and Technology, Xinxiang Medical University, Xinxiang, Henan 453003, People's Republic of China
*Correspondence e-mail: baisuping@xxmu.edu.cn

(Received 5 May 2009; accepted 10 July 2009; online 18 July 2009)

The title compound, 14β-acet­oxy-7α-hydr­oxy-ent-kaur-16-ene-3,15-dione or glaucocalyxin B, C22H30O5, a natural ent-kaurane diterpenoid, is composed of four rings with the expected cis and trans ring junctions. In the crystal structure, there are two mol­ecules in the asymmetric unit related by a noncrystallographic twofold screw axis, and ring A is disordered [ratio occupancies 0.829 (19):0.171 (19)], such that both chair and boat conformations are present, but with the boat conformation as the major component. In the crystal, mol­ecules are linked by inter­molecular O—H⋯O hydrogen bonds.

Related literature

For related literature on the genus Isodon and diterpenoids therefrom, see: Liu et al. (1988[Liu, C. J., Zhao, Z. H., Wang, Q. R., Sun, H. D. & Lin, Z. W. (1988). Acta Bot. Yunnanica, 10, 471-473.]); Kim et al. (1992[Kim, D. S., Chang, R. G., Shen, X. Y., Chen, Y. P. & Sun, H. D. (1992). Phytochemistry, 31, 697-699.]); Sun et al. (2001[Sun, H. D., Xu, Y. L. & Jiang, B. (2001). Diterpenoids from Isodon Species, pp. 4-17, 140. Beijing: Science Press.]); Bai et al. (2005[Bai, S. P., Ma, X. K. & Zhang, J. X. (2005). J. Xinxiang Med. Coll. 22, 297-299.]). For expected bond-length ranges, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data
  • C22H30O5

  • Mr = 374.46

  • Monoclinic, P 21

  • a = 8.485 (4) Å

  • b = 23.786 (10) Å

  • c = 9.930 (4) Å

  • β = 91.039 (17)°

  • V = 2003.8 (15) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.09 mm−1

  • T = 296 K

  • 0.36 × 0.34 × 0.32 mm

Data collection
  • Rigaku R-AXIS RAPID diffractometer

  • Absorption correction: none

  • 19620 measured reflections

  • 4669 independent reflections

  • 2856 reflections with I > 2σ(I)

  • Rint = 0.070

Refinement
  • R[F2 > 2σ(F2)] = 0.063

  • wR(F2) = 0.164

  • S = 1.00

  • 4669 reflections

  • 524 parameters

  • 14 restraints

  • H-atom parameters constrained

  • Δρmax = 0.19 e Å−3

  • Δρmin = −0.20 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2O⋯O1i 0.82 2.09 2.747 (6) 137
O2—H2O⋯O1i 0.82 2.09 2.747 (6) 137
O2′—H2O′⋯O1′i 0.82 2.05 2.764 (5) 146
O2′—H2O′⋯O1*i 0.82 2.24 2.89 (3) 136
Symmetry code: (i) x, y, z-1.

Data collection: RAPID-AUTO (Rigaku, 2004[Rigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.]); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

The title compound (I) is a natural ent-kaurane diterpenoid isolated from the medicinal plant Isodon japonica var. glaucocalyx. This plant has been used in antibacterial, inflammation-diminishing and stomachic agents. The structure has been postulated previously based on spectroscopic methods (Liu et al., 1988; Kim et al.,1992; Bai et al., 2005). In order to further confirm the structure and conformation of (I), a crystal structure analysis, reported here, was undertaken.

The X-ray crystallographic analysis of (I) confirms the previously proposed molecular structure of (I). Fig. 1 shows its conformation: two carbonyl groups located at C3 and C15, while a hydroxyl group and an acetoxyl group adopt α and β-orientations at C7 and C14 respectively. There is a trans junction between ring A (C1–C5/C10) and ring B (C5–C10); cis junctions are present between ring B and ring C (C8/C9/C11–C14), and ring C and ring D (C8/C13–C16).

The crystal structure analysis shows that there are two molecules in the asymmetric unit, each with different bond lengths and angles, but which are within expected ranges (Allen et al., 1987). In both molecules ring B adopts a chair conformation and ring C has a slight-twist chair conformation. Ring A is disordered, such that both chair and boat conformations are present, but with the boat conformation as the major component. The ratios of boat to chair conformations are 66.7%:32.3% for C1–C5/C10, and 82.9%:17.1% for C1'–C5'/C10'. Ring D shows an envelope conformation; the flap atom, C14, lies 0.660 (6) Å from the plane defined by atoms C8, C15, C16 and C13 [0.665 (7) Å for atom C14'].

Compound (I) contains seven chiral centers at C5(S), C7(R), C8(R), C9(S), C10(R), C13(R) and C14(R). Although the absolute configuration could not be reliably determined from anomalous dispersion effects, the negative optical rotation showed this compound to be in the ent-kaurane seuies as reported in genus Isodon (Sun et al., 2001), rather than in the kaurane series, and so allowed us to assign the correct configuration. In the crystal structure, the molecules are linked by O—H···O hydrogen bonds into chains parallel to the c axis (Table 1 and Fig. 2).

Related literature top

For related literature on the genus Isodon and diterpenoids therefrom, see: Liu et al. (1988); Kim et al. (1992); Sun et al. (2001); Bai et al. (2005). For expected bond-length ranges, see: Allen et al. (1987).

Experimental top

The dried and crushed leaves of Isodon japonica var. glaucocalyx (10 kg, collected from Hui Prefecture, Henan Province, China) were extracted four times with Me2CO/H2O (7:3, v/v) at room temperature over a period of seven days. The extract was filtered and the solvent was removed under reduced pressure. The residue was then partitioned between water and AcOEt. After removal of the solvent, the AcOEt residue was separated by repeated silica gel (200–300 mesh) column chromatography and recrystallization from CHCl3/Me2CO(20:1), giving 700 mg of compound (I) (m.p. 463–465 K. Optical rotation: [α]D20 -130 ° (c 0.95, CHCl3). Crystals suitable for X-ray analysis were obtained by slow evaporation of a solution of the compound (I) in Me2CO at room temperature.

Refinement top

All H atoms were included in calculated positions and refined as riding atoms, with C—H = 0.96 Å (CH3), 0.93 and 0.97 Å (CH2), and 0.98 Å (CH), and with Uiso(H) = 1.2 Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were merged. The choice of enantiomer was based on comparison of the optical rotation with that of related compounds with known stereochemistry. Disorder in ring A was identified by peaks on a difference Fourier map. Each group of disordered atoms was refined with common site occupancies, and equivalent atoms were constrained to have the same anisotropic displacement parameters. The bond lengths in the disorder groups were restrained to values of 1.210 (3) Å (for all four CO distances), 1.540 (3) Å (C1—C10, C1—C2, and equivalents) and 1.460 (3) Å (C2'—C3').

Computing details top

Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); 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: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of compound (I). Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the b axis, showing the O—H···O hydrogen bonds as dashed lines.
14β-acetoxy-7α-hydroxy-ent-kaur-16-ene-3,15-dione top
Crystal data top
C22H30O5Dx = 1.241 Mg m3
Mr = 374.46Melting point: 463 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 8.485 (4) ÅCell parameters from 12776 reflections
b = 23.786 (10) Åθ = 3.1–27.6°
c = 9.930 (4) ŵ = 0.09 mm1
β = 91.039 (17)°T = 296 K
V = 2003.8 (15) Å3Block, colourless
Z = 40.36 × 0.34 × 0.32 mm
F(000) = 808
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2856 reflections with I > 2σ(I)
Radiation source: Rotating AnodeRint = 0.070
Graphite monochromatorθmax = 27.5°, θmin = 3.1°
ω scansh = 1011
19620 measured reflectionsk = 3028
4669 independent reflectionsl = 1212
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0896P)2 + 0.022P]
where P = (Fo2 + 2Fc2)/3
4669 reflections(Δ/σ)max = 0.001
524 parametersΔρmax = 0.19 e Å3
14 restraintsΔρmin = 0.20 e Å3
Crystal data top
C22H30O5V = 2003.8 (15) Å3
Mr = 374.46Z = 4
Monoclinic, P21Mo Kα radiation
a = 8.485 (4) ŵ = 0.09 mm1
b = 23.786 (10) ÅT = 296 K
c = 9.930 (4) Å0.36 × 0.34 × 0.32 mm
β = 91.039 (17)°
Data collection top
Rigaku R-AXIS RAPID
diffractometer
2856 reflections with I > 2σ(I)
19620 measured reflectionsRint = 0.070
4669 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06314 restraints
wR(F2) = 0.164H-atom parameters constrained
S = 1.00Δρmax = 0.19 e Å3
4669 reflectionsΔρmin = 0.20 e Å3
524 parameters
Special details top

Experimental. The assignment of absolute structure was based on comparison of the optical rotation with that of related compounds with known stereochemistry.

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) top
xyzUiso*/UeqOcc. (<1)
O20.1468 (4)0.62378 (17)0.4126 (3)0.0622 (9)
H2O0.12230.64210.34550.075*
O30.1799 (5)0.69449 (15)0.3591 (3)0.0678 (10)
O40.0788 (4)0.53978 (13)0.3705 (3)0.0528 (8)
O50.1013 (6)0.4948 (2)0.4969 (5)0.1003 (17)
O10.1366 (10)0.6324 (4)1.1368 (5)0.097 (3)0.677 (9)
C10.1799 (14)0.6575 (9)0.9035 (12)0.0647 (16)0.677 (9)
H1A0.23580.68910.86380.078*0.677 (9)
H1B0.25750.63310.94380.078*0.677 (9)
C20.0687 (12)0.6796 (5)1.0157 (8)0.077 (3)0.677 (9)
H2A0.05020.71930.99950.092*0.677 (9)
H2B0.12270.67661.10070.092*0.677 (9)
O1"0.1487 (19)0.6698 (7)1.1325 (10)0.097 (3)0.323 (9)
C1"0.173 (3)0.6548 (19)0.9108 (18)0.0647 (16)0.323 (9)
H1C0.17630.69490.89320.078*0.323 (9)
H1D0.28050.64180.92000.078*0.323 (9)
C2"0.082 (3)0.6443 (12)1.0439 (18)0.077 (3)0.323 (9)
H2C0.11910.67011.11170.092*0.323 (9)
H2D0.10300.60641.07460.092*0.323 (9)
C30.0870 (6)0.6513 (2)1.0308 (4)0.0596 (13)
C40.1788 (6)0.6446 (2)0.9042 (4)0.0522 (11)
C50.0705 (5)0.64895 (18)0.7754 (4)0.0391 (9)
H50.05610.68930.75970.047*
C60.1477 (5)0.6264 (2)0.6482 (4)0.0444 (10)
H6A0.25350.64160.64250.053*
H6B0.15590.58580.65420.053*
C70.0559 (5)0.64180 (19)0.5227 (4)0.0442 (10)
H70.05130.68290.51890.053*
C80.1146 (5)0.62046 (18)0.5220 (4)0.0380 (9)
C90.1924 (5)0.63960 (18)0.6580 (4)0.0443 (10)
H90.19180.68080.65430.053*
C100.0983 (5)0.62477 (17)0.7901 (3)0.0428 (10)
C110.3706 (6)0.6233 (2)0.6593 (5)0.0604 (13)
H11A0.40330.62200.75230.073*
H11B0.43000.65320.61540.073*
C120.4176 (6)0.5680 (3)0.5925 (5)0.0669 (14)
H12A0.53060.56740.57620.080*
H12B0.39070.53700.65210.080*
C130.3319 (6)0.5609 (2)0.4582 (5)0.0566 (12)
H130.36730.52710.41000.068*
C140.1555 (5)0.55858 (18)0.4915 (4)0.0462 (10)
H140.13200.53400.56850.055*
C150.2106 (6)0.6491 (2)0.4093 (4)0.0500 (11)
C160.3460 (6)0.6124 (2)0.3714 (5)0.0575 (13)
C170.4607 (8)0.6273 (3)0.2837 (6)0.091 (2)
H17A0.45830.66250.24280.109*
H17B0.54260.60250.26380.109*
C180.2971 (7)0.6944 (3)0.9021 (5)0.0727 (16)
H18A0.24050.72920.90770.087*
H18B0.35480.69350.81990.087*
H18C0.36920.69130.97740.087*
C190.2760 (6)0.5904 (2)0.9127 (5)0.0645 (14)
H19A0.34200.59130.99220.077*
H19B0.34050.58740.83460.077*
H19C0.20640.55870.91660.077*
C200.0951 (6)0.5615 (2)0.8243 (5)0.0592 (13)
H20A0.02390.54250.76550.071*
H20B0.19900.54610.81250.071*
H20C0.06040.55650.91610.071*
C210.0542 (7)0.5098 (2)0.3887 (5)0.0637 (14)
C220.1285 (10)0.4971 (3)0.2562 (7)0.106 (3)
H22A0.22760.47860.27170.128*
H22B0.14530.53160.20810.128*
H22C0.05990.47310.20410.128*
O2'0.3469 (4)0.85034 (16)0.0269 (3)0.0586 (9)
H2O'0.39750.84770.04240.070*
O3'0.6721 (5)0.77771 (15)0.0252 (4)0.0660 (10)
O4'0.5734 (4)0.93369 (14)0.0081 (3)0.0550 (9)
O5'0.4016 (6)0.9800 (2)0.1187 (4)0.1003 (16)
O1'0.3864 (11)0.8451 (4)0.7516 (5)0.090 (3)0.829 (19)
C1'0.6870 (10)0.8126 (4)0.5231 (7)0.064 (2)0.829 (19)
H1'10.74210.78070.48550.077*0.829 (19)
H1'20.76490.83680.56610.077*0.829 (19)
C2'0.5725 (10)0.7913 (5)0.6304 (8)0.072 (3)0.829 (19)
H2'10.54200.75310.60760.087*0.829 (19)
H2'20.62840.79000.71640.087*0.829 (19)
O1*0.350 (5)0.818 (2)0.746 (3)0.090 (3)0.171 (19)
C1*0.666 (8)0.806 (2)0.521 (2)0.064 (2)0.171 (19)
H1*10.63690.76800.50050.077*0.171 (19)
H1*20.78050.80850.52550.077*0.171 (19)
C2*0.599 (3)0.8233 (17)0.658 (2)0.039 (8)0.171 (19)
H2*10.63150.79620.72640.047*0.171 (19)
H2*20.63870.85990.68480.047*0.171 (19)
C3'0.4290 (6)0.8247 (2)0.6466 (4)0.0588 (13)
C4'0.3273 (6)0.8314 (2)0.5166 (4)0.0476 (11)
C5'0.4329 (5)0.82451 (17)0.3899 (4)0.0399 (9)
H5'0.44100.78390.37540.048*
C6'0.3526 (5)0.84739 (19)0.2639 (4)0.0438 (10)
H6'10.34790.88810.26940.053*
H6'20.24540.83330.25830.053*
C7'0.4394 (5)0.83058 (19)0.1374 (4)0.0416 (9)
H7'0.44070.78940.13310.050*
C8'0.6112 (5)0.85099 (16)0.1395 (4)0.0373 (9)
C9'0.6931 (5)0.83068 (19)0.2744 (4)0.0429 (10)
H9'0.68950.78950.26940.051*
C10'0.6046 (5)0.84534 (16)0.4075 (3)0.0415 (10)
C11'0.8721 (5)0.8451 (2)0.2767 (5)0.0597 (13)
H11C0.90920.84510.36970.072*
H11D0.92750.81540.23050.072*
C12'0.9178 (6)0.9010 (3)0.2136 (5)0.0667 (14)
H12C0.89450.93130.27540.080*
H12D1.03020.90130.19770.080*
C13'0.8294 (6)0.9105 (2)0.0819 (5)0.0585 (12)
H13'0.86460.94490.03700.070*
C14'0.6525 (5)0.91288 (19)0.1136 (4)0.0459 (10)
H14'0.63150.93660.19190.055*
C15'0.7050 (6)0.8232 (2)0.0252 (4)0.0501 (11)
C16'0.8382 (6)0.8602 (2)0.0094 (5)0.0587 (13)
C17'0.9457 (7)0.8461 (3)0.0995 (6)0.088 (2)
H17C0.93890.81170.14370.106*
H17D1.02770.87070.11830.106*
C18'0.2105 (7)0.7819 (3)0.5205 (6)0.0732 (16)
H18D0.13800.78750.59240.088*
H18E0.26740.74750.53500.088*
H18F0.15320.77980.43630.088*
C19'0.2339 (6)0.8872 (2)0.5239 (5)0.0613 (13)
H19D0.18040.88920.60810.074*
H19E0.15810.88870.45100.074*
H19F0.30540.91830.51700.074*
C20'0.6079 (6)0.9084 (2)0.4436 (5)0.0559 (12)
H20D0.54550.92900.37880.067*
H20E0.71460.92170.44270.067*
H20F0.56570.91370.53170.067*
C21'0.4459 (7)0.9658 (2)0.0084 (5)0.0643 (14)
C22'0.3709 (9)0.9785 (3)0.1242 (7)0.095 (2)
H22D0.27150.95940.13150.114*
H22E0.43840.96610.19480.114*
H22F0.35421.01830.13200.114*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.053 (2)0.099 (3)0.0356 (15)0.0010 (19)0.0084 (15)0.0041 (16)
O30.087 (3)0.059 (2)0.057 (2)0.0069 (19)0.0092 (19)0.0131 (17)
O40.063 (2)0.0525 (18)0.0430 (16)0.0125 (16)0.0033 (15)0.0103 (13)
O50.112 (4)0.113 (4)0.076 (3)0.068 (3)0.006 (3)0.016 (2)
O10.120 (4)0.138 (8)0.033 (2)0.059 (6)0.007 (2)0.027 (4)
C10.051 (3)0.097 (5)0.046 (3)0.013 (3)0.007 (2)0.016 (3)
C20.095 (6)0.097 (8)0.038 (4)0.032 (7)0.001 (4)0.015 (5)
O1"0.120 (4)0.138 (8)0.033 (2)0.059 (6)0.007 (2)0.027 (4)
C1"0.051 (3)0.097 (5)0.046 (3)0.013 (3)0.007 (2)0.016 (3)
C2"0.095 (6)0.097 (8)0.038 (4)0.032 (7)0.001 (4)0.015 (5)
C30.069 (4)0.076 (3)0.033 (2)0.003 (3)0.006 (2)0.000 (2)
C40.056 (3)0.064 (3)0.037 (2)0.004 (2)0.002 (2)0.002 (2)
C50.045 (2)0.038 (2)0.0333 (18)0.0027 (18)0.0041 (17)0.0023 (16)
C60.037 (2)0.061 (3)0.036 (2)0.006 (2)0.0068 (18)0.0014 (19)
C70.050 (3)0.053 (2)0.0302 (18)0.002 (2)0.0048 (18)0.0022 (17)
C80.038 (2)0.043 (2)0.0332 (18)0.0036 (18)0.0027 (17)0.0001 (16)
C90.041 (2)0.046 (2)0.046 (2)0.0038 (19)0.0025 (19)0.0091 (18)
C100.044 (2)0.047 (2)0.037 (2)0.001 (2)0.0069 (18)0.0002 (18)
C110.037 (3)0.088 (4)0.056 (3)0.006 (3)0.005 (2)0.015 (3)
C120.044 (3)0.088 (4)0.069 (3)0.018 (3)0.003 (2)0.013 (3)
C130.049 (3)0.060 (3)0.061 (3)0.007 (2)0.005 (2)0.016 (2)
C140.054 (3)0.042 (2)0.042 (2)0.001 (2)0.003 (2)0.0048 (18)
C150.059 (3)0.052 (3)0.039 (2)0.015 (2)0.001 (2)0.003 (2)
C160.048 (3)0.068 (3)0.057 (3)0.011 (2)0.009 (2)0.011 (2)
C170.068 (4)0.103 (5)0.100 (5)0.016 (4)0.034 (4)0.010 (4)
C180.065 (4)0.098 (4)0.055 (3)0.025 (3)0.010 (3)0.003 (3)
C190.055 (3)0.088 (4)0.051 (3)0.011 (3)0.012 (2)0.011 (2)
C200.059 (3)0.066 (3)0.052 (3)0.015 (2)0.001 (2)0.015 (2)
C210.070 (4)0.063 (3)0.059 (3)0.021 (3)0.004 (3)0.006 (2)
C220.128 (7)0.109 (5)0.084 (4)0.039 (5)0.029 (4)0.035 (4)
O2'0.0475 (19)0.096 (3)0.0321 (14)0.0080 (18)0.0098 (13)0.0048 (16)
O3'0.075 (3)0.063 (2)0.060 (2)0.0144 (19)0.0030 (18)0.0161 (17)
O4'0.063 (2)0.0590 (19)0.0433 (16)0.0187 (17)0.0021 (15)0.0113 (14)
O5'0.121 (4)0.108 (3)0.072 (3)0.068 (3)0.003 (3)0.019 (2)
O1'0.115 (5)0.125 (7)0.0296 (18)0.023 (5)0.004 (2)0.004 (3)
C1'0.062 (5)0.087 (4)0.043 (2)0.012 (4)0.013 (2)0.010 (3)
C2'0.084 (6)0.085 (7)0.048 (4)0.009 (5)0.009 (4)0.025 (4)
O1*0.115 (5)0.125 (7)0.0296 (18)0.023 (5)0.004 (2)0.004 (3)
C1*0.062 (5)0.087 (4)0.043 (2)0.012 (4)0.013 (2)0.010 (3)
C2*0.046 (16)0.046 (19)0.025 (11)0.016 (13)0.019 (10)0.005 (12)
C3'0.075 (4)0.067 (3)0.033 (2)0.012 (3)0.002 (2)0.005 (2)
C4'0.053 (3)0.054 (3)0.035 (2)0.003 (2)0.0004 (19)0.0050 (19)
C5'0.047 (2)0.042 (2)0.0309 (18)0.0028 (18)0.0043 (17)0.0004 (16)
C6'0.040 (2)0.056 (3)0.035 (2)0.003 (2)0.0070 (18)0.0007 (19)
C7'0.041 (2)0.052 (2)0.0312 (19)0.000 (2)0.0090 (17)0.0043 (18)
C8'0.038 (2)0.039 (2)0.0343 (19)0.0083 (18)0.0045 (17)0.0039 (16)
C9'0.041 (2)0.047 (2)0.041 (2)0.0046 (19)0.0070 (18)0.0029 (18)
C10'0.043 (2)0.047 (2)0.034 (2)0.0011 (19)0.0075 (17)0.0014 (17)
C11'0.040 (3)0.082 (3)0.057 (3)0.010 (3)0.010 (2)0.004 (2)
C12'0.041 (3)0.092 (4)0.067 (3)0.010 (3)0.001 (2)0.004 (3)
C13'0.058 (3)0.059 (3)0.059 (3)0.001 (2)0.006 (2)0.007 (2)
C14'0.047 (3)0.049 (2)0.041 (2)0.004 (2)0.004 (2)0.0032 (19)
C15'0.047 (3)0.062 (3)0.041 (2)0.014 (2)0.002 (2)0.006 (2)
C16'0.052 (3)0.079 (3)0.045 (2)0.014 (3)0.004 (2)0.011 (2)
C17'0.071 (4)0.115 (5)0.080 (4)0.029 (4)0.029 (3)0.008 (4)
C18'0.078 (4)0.084 (4)0.057 (3)0.028 (3)0.006 (3)0.009 (3)
C19'0.056 (3)0.076 (3)0.052 (3)0.013 (3)0.007 (2)0.001 (2)
C20'0.059 (3)0.055 (3)0.054 (3)0.012 (2)0.001 (2)0.013 (2)
C21'0.075 (4)0.051 (3)0.066 (3)0.024 (3)0.006 (3)0.006 (2)
C22'0.092 (5)0.100 (5)0.091 (4)0.042 (4)0.018 (4)0.027 (4)
Geometric parameters (Å, º) top
O2—C71.416 (5)O2'—C7'1.417 (5)
O2—H2O0.8200O2'—H2O'0.8200
O3—C151.218 (6)O3'—C15'1.223 (6)
O4—C211.344 (6)O4'—C21'1.337 (6)
O4—C141.447 (5)O4'—C14'1.458 (5)
O5—C211.195 (6)O5'—C21'1.213 (6)
O1—C31.212 (3)O1'—C3'1.211 (3)
C1—C21.540 (3)C1'—C2'1.540 (3)
C1—C101.543 (3)C1'—C10'1.543 (3)
C1—H1A0.9700C1'—H1'10.9700
C1—H1B0.9700C1'—H1'20.9700
C2—C31.488 (11)C2'—C3'1.464 (3)
C2—H2A0.9700C2'—H2'10.9700
C2—H2B0.9700C2'—H2'20.9700
O1"—C31.212 (3)O1*—C3'1.210 (3)
C1"—C2"1.540 (3)C1*—C2*1.540 (3)
C1"—C101.541 (3)C1*—C10'1.541 (3)
C1"—H1C0.9700C1*—H1*10.9700
C1"—H1D0.9700C1*—H1*20.9700
C2"—C31.45 (3)C2*—C3'1.45 (3)
C2"—H2C0.9700C2*—H2*10.9700
C2"—H2D0.9700C2*—H2*20.9700
C3—C41.499 (6)C3'—C4'1.548 (6)
C4—C191.532 (7)C4'—C18'1.541 (7)
C4—C181.553 (7)C4'—C19'1.548 (7)
C4—C51.565 (6)C4'—C5'1.567 (6)
C5—C61.530 (5)C5'—C6'1.515 (5)
C5—C101.553 (6)C5'—C10'1.545 (6)
C5—H50.9800C5'—H5'0.9800
C6—C71.502 (6)C6'—C7'1.521 (5)
C6—H6A0.9700C6'—H6'10.9700
C6—H6B0.9700C6'—H6'20.9700
C7—C81.533 (6)C7'—C8'1.536 (6)
C7—H70.9800C7'—H7'0.9800
C8—C151.533 (6)C8'—C14'1.536 (6)
C8—C141.541 (6)C8'—C15'1.546 (6)
C8—C91.580 (5)C8'—C9'1.574 (5)
C9—C111.562 (6)C9'—C11'1.558 (6)
C9—C101.563 (6)C9'—C10'1.571 (5)
C9—H90.9800C9'—H9'0.9800
C10—C201.543 (7)C10'—C20'1.542 (6)
C11—C121.524 (8)C11'—C12'1.521 (8)
C11—H11A0.9700C11'—H11C0.9700
C11—H11B0.9700C11'—H11D0.9700
C12—C131.540 (7)C12'—C13'1.512 (8)
C12—H12A0.9700C12'—H12C0.9700
C12—H12B0.9700C12'—H12D0.9700
C13—C161.502 (7)C13'—C16'1.504 (7)
C13—C141.528 (7)C13'—C14'1.540 (7)
C13—H130.9800C13'—H13'0.9800
C14—H140.9800C14'—H14'0.9800
C15—C161.487 (7)C15'—C16'1.478 (7)
C16—C171.342 (8)C16'—C17'1.332 (7)
C17—H17A0.9300C17'—H17C0.9300
C17—H17B0.9300C17'—H17D0.9300
C18—H18A0.9600C18'—H18D0.9600
C18—H18B0.9600C18'—H18E0.9600
C18—H18C0.9600C18'—H18F0.9600
C19—H19A0.9600C19'—H19D0.9600
C19—H19B0.9600C19'—H19E0.9600
C19—H19C0.9600C19'—H19F0.9600
C20—H20A0.9600C20'—H20D0.9600
C20—H20B0.9600C20'—H20E0.9600
C20—H20C0.9600C20'—H20F0.9600
C21—C221.499 (8)C21'—C22'1.482 (8)
C22—H22A0.9600C22'—H22D0.9600
C22—H22B0.9600C22'—H22E0.9600
C22—H22C0.9600C22'—H22F0.9600
C7—O2—H2O109.5C7'—O2'—H2O'109.5
C21—O4—C14116.2 (4)C21'—O4'—C14'117.0 (4)
C2—C1—C10115.1 (7)C2'—C1'—C10'113.4 (5)
C2—C1—H1A108.5C2'—C1'—H1'1108.9
C10—C1—H1A108.5C10'—C1'—H1'1108.9
C2—C1—H1B108.5C2'—C1'—H1'2108.9
C10—C1—H1B108.5C10'—C1'—H1'2108.9
H1A—C1—H1B107.5H1'1—C1'—H1'2107.7
C3—C2—C1116.7 (7)C3'—C2'—C1'115.7 (5)
C3—C2—H2A108.1C3'—C2'—H2'1108.4
C1—C2—H2A108.1C1'—C2'—H2'1108.4
C3—C2—H2B108.1C3'—C2'—H2'2108.4
C1—C2—H2B108.1C1'—C2'—H2'2108.4
H2A—C2—H2B107.3H2'1—C2'—H2'2107.4
C2"—C1"—C10112.6 (12)C2*—C1*—C10'111.4 (16)
C2"—C1"—H1C109.1C2*—C1*—H1*1109.3
C10—C1"—H1C109.1C10'—C1*—H1*1109.3
C2"—C1"—H1D109.1C2*—C1*—H1*2109.3
C10—C1"—H1D109.1C10'—C1*—H1*2109.3
H1C—C1"—H1D107.8H1*1—C1*—H1*2108.0
C3—C2"—C1"112.7 (19)C3'—C2*—C1*109 (3)
C3—C2"—H2C109.0C3'—C2*—H2*1110.0
C1"—C2"—H2C109.0C1*—C2*—H2*1110.0
C3—C2"—H2D109.0C3'—C2*—H2*2110.0
C1"—C2"—H2D109.0C1*—C2*—H2*2110.0
H2C—C2"—H2D107.8H2*1—C2*—H2*2108.3
O1"—C3—O143.4 (7)O1*—C3'—O1'34 (2)
O1"—C3—C2"112.3 (12)O1*—C3'—C2*120 (2)
O1—C3—C2"102.0 (10)O1'—C3'—C2*104.7 (12)
O1"—C3—C2106.7 (9)O1*—C3'—C2'120 (2)
O1—C3—C2123.3 (6)O1'—C3'—C2'125.0 (7)
C2"—C3—C235.4 (9)C2*—C3'—C2'33.5 (12)
O1"—C3—C4121.0 (9)O1*—C3'—C4'113 (2)
O1—C3—C4120.7 (6)O1'—C3'—C4'120.4 (5)
C2"—C3—C4126.3 (8)C2*—C3'—C4'127.6 (10)
C2—C3—C4115.9 (5)C2'—C3'—C4'114.6 (5)
C3—C4—C19109.3 (4)C18'—C4'—C19'108.9 (4)
C3—C4—C18106.0 (4)C18'—C4'—C3'104.4 (4)
C19—C4—C18107.2 (4)C19'—C4'—C3'109.2 (4)
C3—C4—C5111.8 (4)C18'—C4'—C5'108.5 (4)
C19—C4—C5114.1 (4)C19'—C4'—C5'115.3 (3)
C18—C4—C5108.0 (4)C3'—C4'—C5'109.9 (4)
C6—C5—C10110.9 (3)C6'—C5'—C10'112.8 (3)
C6—C5—C4113.5 (4)C6'—C5'—C4'111.8 (4)
C10—C5—C4115.4 (3)C10'—C5'—C4'115.3 (3)
C6—C5—H5105.4C6'—C5'—H5'105.3
C10—C5—H5105.4C10'—C5'—H5'105.3
C4—C5—H5105.4C4'—C5'—H5'105.3
C7—C6—C5112.1 (4)C5'—C6'—C7'111.8 (4)
C7—C6—H6A109.2C5'—C6'—H6'1109.3
C5—C6—H6A109.2C7'—C6'—H6'1109.3
C7—C6—H6B109.2C5'—C6'—H6'2109.3
C5—C6—H6B109.2C7'—C6'—H6'2109.3
H6A—C6—H6B107.9H6'1—C6'—H6'2107.9
O2—C7—C6106.6 (4)O2'—C7'—C6'106.4 (3)
O2—C7—C8115.1 (4)O2'—C7'—C8'114.7 (3)
C6—C7—C8113.5 (3)C6'—C7'—C8'112.3 (3)
O2—C7—H7107.1O2'—C7'—H7'107.7
C6—C7—H7107.1C6'—C7'—H7'107.7
C8—C7—H7107.1C8'—C7'—H7'107.7
C15—C8—C7110.2 (4)C14'—C8'—C7'121.3 (3)
C15—C8—C1499.6 (3)C14'—C8'—C15'99.5 (3)
C7—C8—C14121.8 (4)C7'—C8'—C15'110.9 (3)
C15—C8—C9105.7 (3)C14'—C8'—C9'109.8 (3)
C7—C8—C9108.0 (3)C7'—C8'—C9'108.6 (3)
C14—C8—C9110.3 (3)C15'—C8'—C9'105.6 (3)
C11—C9—C10114.7 (4)C11'—C9'—C10'114.8 (4)
C11—C9—C8110.8 (3)C11'—C9'—C8'111.1 (3)
C10—C9—C8115.9 (3)C10'—C9'—C8'116.0 (3)
C11—C9—H9104.7C11'—C9'—H9'104.5
C10—C9—H9104.7C10'—C9'—H9'104.5
C8—C9—H9104.7C8'—C9'—H9'104.5
C1"—C10—C20106.6 (18)C1*—C10'—C20'114 (2)
C1"—C10—C14.2 (17)C1*—C10'—C1'8 (3)
C20—C10—C1109.7 (9)C20'—C10'—C1'108.2 (5)
C1"—C10—C5107.1 (16)C1*—C10'—C5'101 (3)
C20—C10—C5111.7 (4)C20'—C10'—C5'110.6 (4)
C1—C10—C5108.0 (7)C1'—C10'—C5'109.6 (5)
C1"—C10—C9109.7 (9)C1*—C10'—C9'108.7 (12)
C20—C10—C9114.3 (4)C20'—C10'—C9'113.8 (3)
C1—C10—C9105.6 (6)C1'—C10'—C9'107.2 (4)
C5—C10—C9107.2 (3)C5'—C10'—C9'107.3 (3)
C12—C11—C9117.1 (4)C12'—C11'—C9'116.3 (4)
C12—C11—H11A108.0C12'—C11'—H11C108.2
C9—C11—H11A108.0C9'—C11'—H11C108.2
C12—C11—H11B108.0C12'—C11'—H11D108.2
C9—C11—H11B108.0C9'—C11'—H11D108.2
H11A—C11—H11B107.3H11C—C11'—H11D107.4
C11—C12—C13110.3 (4)C13'—C12'—C11'111.2 (4)
C11—C12—H12A109.6C13'—C12'—H12C109.4
C13—C12—H12A109.6C11'—C12'—H12C109.4
C11—C12—H12B109.6C13'—C12'—H12D109.4
C13—C12—H12B109.6C11'—C12'—H12D109.4
H12A—C12—H12B108.1H12C—C12'—H12D108.0
C16—C13—C14102.8 (4)C16'—C13'—C12'111.9 (4)
C16—C13—C12112.0 (4)C16'—C13'—C14'102.2 (4)
C14—C13—C12107.0 (4)C12'—C13'—C14'107.4 (4)
C16—C13—H13111.5C16'—C13'—H13'111.6
C14—C13—H13111.5C12'—C13'—H13'111.6
C12—C13—H13111.5C14'—C13'—H13'111.6
O4—C14—C13106.6 (4)O4'—C14'—C8'111.2 (4)
O4—C14—C8110.8 (3)O4'—C14'—C13'106.2 (3)
C13—C14—C8103.0 (4)C8'—C14'—C13'103.0 (3)
O4—C14—H14112.0O4'—C14'—H14'112.0
C13—C14—H14112.0C8'—C14'—H14'112.0
C8—C14—H14112.0C13'—C14'—H14'112.0
O3—C15—C16125.9 (5)O3'—C15'—C16'127.0 (4)
O3—C15—C8125.3 (5)O3'—C15'—C8'124.2 (4)
C16—C15—C8108.7 (4)C16'—C15'—C8'108.8 (4)
C17—C16—C15123.8 (5)C17'—C16'—C15'122.9 (6)
C17—C16—C13129.7 (6)C17'—C16'—C13'130.3 (6)
C15—C16—C13106.3 (4)C15'—C16'—C13'106.7 (4)
C16—C17—H17A120.0C16'—C17'—H17C120.0
C16—C17—H17B120.0C16'—C17'—H17D120.0
H17A—C17—H17B120.0H17C—C17'—H17D120.0
C4—C18—H18A109.5C4'—C18'—H18D109.5
C4—C18—H18B109.5C4'—C18'—H18E109.5
H18A—C18—H18B109.5H18D—C18'—H18E109.5
C4—C18—H18C109.5C4'—C18'—H18F109.5
H18A—C18—H18C109.5H18D—C18'—H18F109.5
H18B—C18—H18C109.5H18E—C18'—H18F109.5
C4—C19—H19A109.5C4'—C19'—H19D109.5
C4—C19—H19B109.5C4'—C19'—H19E109.5
H19A—C19—H19B109.5H19D—C19'—H19E109.5
C4—C19—H19C109.5C4'—C19'—H19F109.5
H19A—C19—H19C109.5H19D—C19'—H19F109.5
H19B—C19—H19C109.5H19E—C19'—H19F109.5
C10—C20—H20A109.5C10'—C20'—H20D109.5
C10—C20—H20B109.5C10'—C20'—H20E109.5
H20A—C20—H20B109.5H20D—C20'—H20E109.5
C10—C20—H20C109.5C10'—C20'—H20F109.5
H20A—C20—H20C109.5H20D—C20'—H20F109.5
H20B—C20—H20C109.5H20E—C20'—H20F109.5
O5—C21—O4123.1 (5)O5'—C21'—O4'122.3 (5)
O5—C21—C22126.1 (6)O5'—C21'—C22'127.6 (5)
O4—C21—C22110.7 (5)O4'—C21'—C22'110.1 (5)
C21—C22—H22A109.5C21'—C22'—H22D109.5
C21—C22—H22B109.5C21'—C22'—H22E109.5
H22A—C22—H22B109.5H22D—C22'—H22E109.5
C21—C22—H22C109.5C21'—C22'—H22F109.5
H22A—C22—H22C109.5H22D—C22'—H22F109.5
H22B—C22—H22C109.5H22E—C22'—H22F109.5
C10—C1—C2—C321 (2)C10'—C1*—C2*—C3'54 (6)
C10—C1"—C2"—C347 (4)C1*—C2*—C3'—O1*156 (4)
C1"—C2"—C3—O1"147 (2)C1*—C2*—C3'—O1'171 (3)
C1"—C2"—C3—O1169 (2)C1*—C2*—C3'—C2'56 (3)
C1"—C2"—C3—C259 (2)C1*—C2*—C3'—C4'22 (4)
C1"—C2"—C3—C426 (3)C1'—C2'—C3'—O1*164 (3)
C1—C2—C3—O1"172.2 (14)C1'—C2'—C3'—O1'124.4 (13)
C1—C2—C3—O1127.4 (14)C1'—C2'—C3'—C2*64 (2)
C1—C2—C3—C2"67 (2)C1'—C2'—C3'—C4'57.3 (12)
C1—C2—C3—C449.8 (13)O1*—C3'—C4'—C18'50 (3)
O1"—C3—C4—C1980.5 (11)O1'—C3'—C4'—C18'87.0 (8)
O1—C3—C4—C1929.5 (9)C2*—C3'—C4'—C18'128 (2)
C2"—C3—C4—C19107.9 (14)C2'—C3'—C4'—C18'91.3 (7)
C2—C3—C4—C19147.8 (7)O1*—C3'—C4'—C19'66 (3)
O1"—C3—C4—C1834.7 (11)O1'—C3'—C4'—C19'29.4 (9)
O1—C3—C4—C1885.8 (8)C2*—C3'—C4'—C19'116 (2)
C2"—C3—C4—C18136.9 (14)C2'—C3'—C4'—C19'152.3 (6)
C2—C3—C4—C1897.0 (7)O1*—C3'—C4'—C5'166 (3)
O1"—C3—C4—C5152.2 (10)O1'—C3'—C4'—C5'156.8 (8)
O1—C3—C4—C5156.8 (7)C2*—C3'—C4'—C5'12 (2)
C2"—C3—C4—C519.4 (15)C2'—C3'—C4'—C5'24.8 (7)
C2—C3—C4—C520.5 (8)C18'—C4'—C5'—C6'83.3 (5)
C3—C4—C5—C6163.8 (4)C19'—C4'—C5'—C6'39.1 (5)
C19—C4—C5—C639.2 (5)C3'—C4'—C5'—C6'163.1 (4)
C18—C4—C5—C679.9 (5)C18'—C4'—C5'—C10'146.2 (4)
C3—C4—C5—C1034.3 (5)C19'—C4'—C5'—C10'91.3 (5)
C19—C4—C5—C1090.3 (5)C3'—C4'—C5'—C10'32.6 (5)
C18—C4—C5—C10150.6 (4)C10'—C5'—C6'—C7'59.5 (5)
C10—C5—C6—C760.0 (5)C4'—C5'—C6'—C7'168.8 (4)
C4—C5—C6—C7168.2 (4)C5'—C6'—C7'—O2'175.4 (3)
C5—C6—C7—O2174.2 (3)C5'—C6'—C7'—C8'58.4 (5)
C5—C6—C7—C858.2 (5)O2'—C7'—C8'—C14'45.9 (5)
O2—C7—C8—C1570.4 (5)C6'—C7'—C8'—C14'75.7 (5)
C6—C7—C8—C15166.5 (3)O2'—C7'—C8'—C15'70.0 (4)
O2—C7—C8—C1445.5 (5)C6'—C7'—C8'—C15'168.3 (4)
C6—C7—C8—C1477.6 (5)O2'—C7'—C8'—C9'174.4 (3)
O2—C7—C8—C9174.6 (3)C6'—C7'—C8'—C9'52.8 (4)
C6—C7—C8—C951.5 (5)C14'—C8'—C9'—C11'50.7 (4)
C15—C8—C9—C1157.6 (5)C7'—C8'—C9'—C11'174.6 (4)
C7—C8—C9—C11175.5 (4)C15'—C8'—C9'—C11'55.7 (5)
C14—C8—C9—C1149.2 (5)C14'—C8'—C9'—C10'82.8 (4)
C15—C8—C9—C10169.5 (4)C7'—C8'—C9'—C10'51.9 (4)
C7—C8—C9—C1051.6 (5)C15'—C8'—C9'—C10'170.8 (4)
C14—C8—C9—C1083.7 (4)C2*—C1*—C10'—C20'45 (6)
C2"—C1"—C10—C2058 (3)C2*—C1*—C10'—C1'92 (11)
C2"—C1"—C10—C561 (3)C2*—C1*—C10'—C5'74 (5)
C2"—C1"—C10—C9177 (2)C2*—C1*—C10'—C9'173 (4)
C2—C1—C10—C2091.6 (15)C2'—C1'—C10'—C1*43 (9)
C2—C1—C10—C530.3 (17)C2'—C1'—C10'—C20'92.9 (9)
C2—C1—C10—C9144.8 (13)C2'—C1'—C10'—C5'27.7 (10)
C6—C5—C10—C1"173.6 (14)C2'—C1'—C10'—C9'143.9 (8)
C4—C5—C10—C1"55.6 (14)C6'—C5'—C10'—C1*168.0 (14)
C6—C5—C10—C2070.0 (4)C4'—C5'—C10'—C1*62.0 (14)
C4—C5—C10—C2060.8 (4)C6'—C5'—C10'—C20'70.6 (4)
C6—C5—C10—C1169.3 (8)C4'—C5'—C10'—C20'59.4 (4)
C4—C5—C10—C159.9 (9)C6'—C5'—C10'—C1'170.3 (5)
C6—C5—C10—C955.9 (4)C4'—C5'—C10'—C1'59.7 (6)
C4—C5—C10—C9173.3 (3)C6'—C5'—C10'—C9'54.1 (4)
C11—C9—C10—C1"59 (2)C4'—C5'—C10'—C9'175.9 (3)
C8—C9—C10—C1"170 (2)C11'—C9'—C10'—C1*67 (3)
C11—C9—C10—C2061.0 (5)C8'—C9'—C10'—C1*161 (3)
C8—C9—C10—C2070.1 (5)C11'—C9'—C10'—C20'61.1 (5)
C11—C9—C10—C159.7 (10)C8'—C9'—C10'—C20'70.7 (5)
C8—C9—C10—C1169.2 (9)C11'—C9'—C10'—C1'58.6 (6)
C11—C9—C10—C5174.7 (4)C8'—C9'—C10'—C1'169.7 (6)
C8—C9—C10—C554.2 (4)C11'—C9'—C10'—C5'176.3 (4)
C10—C9—C11—C1297.5 (5)C8'—C9'—C10'—C5'52.0 (4)
C8—C9—C11—C1236.1 (6)C10'—C9'—C11'—C12'96.8 (5)
C9—C11—C12—C1342.9 (7)C8'—C9'—C11'—C12'37.2 (6)
C11—C12—C13—C1649.3 (6)C9'—C11'—C12'—C13'43.4 (6)
C11—C12—C13—C1462.6 (6)C11'—C12'—C13'—C16'49.3 (6)
C21—O4—C14—C13149.3 (4)C11'—C12'—C13'—C14'62.1 (5)
C21—O4—C14—C899.4 (5)C21'—O4'—C14'—C8'102.2 (5)
C16—C13—C14—O474.1 (4)C21'—O4'—C14'—C13'146.4 (4)
C12—C13—C14—O4167.8 (4)C7'—C8'—C14'—O4'49.8 (5)
C16—C13—C14—C842.5 (4)C15'—C8'—C14'—O4'71.8 (4)
C12—C13—C14—C875.6 (4)C9'—C8'—C14'—O4'177.8 (3)
C15—C8—C14—O471.9 (4)C7'—C8'—C14'—C13'163.2 (4)
C7—C8—C14—O449.2 (5)C15'—C8'—C14'—C13'41.6 (4)
C9—C8—C14—O4177.3 (3)C9'—C8'—C14'—C13'68.9 (4)
C15—C8—C14—C1341.7 (4)C16'—C13'—C14'—O4'73.8 (4)
C7—C8—C14—C13162.8 (4)C12'—C13'—C14'—O4'168.3 (4)
C9—C8—C14—C1369.1 (4)C16'—C13'—C14'—C8'43.1 (4)
C7—C8—C15—O324.0 (6)C12'—C13'—C14'—C8'74.7 (4)
C14—C8—C15—O3153.2 (4)C14'—C8'—C15'—O3'154.8 (5)
C9—C8—C15—O392.4 (5)C7'—C8'—C15'—O3'26.0 (6)
C7—C8—C15—C16155.7 (3)C9'—C8'—C15'—O3'91.4 (5)
C14—C8—C15—C1626.5 (4)C14'—C8'—C15'—C16'25.8 (4)
C9—C8—C15—C1687.9 (4)C7'—C8'—C15'—C16'154.7 (4)
O3—C15—C16—C176.3 (8)C9'—C8'—C15'—C16'87.9 (4)
C8—C15—C16—C17174.1 (5)O3'—C15'—C16'—C17'3.1 (8)
O3—C15—C16—C13178.7 (4)C8'—C15'—C16'—C17'176.2 (5)
C8—C15—C16—C131.0 (5)O3'—C15'—C16'—C13'179.1 (5)
C14—C13—C16—C17159.8 (5)C8'—C15'—C16'—C13'0.3 (5)
C12—C13—C16—C1785.6 (7)C12'—C13'—C16'—C17'87.3 (7)
C14—C13—C16—C1525.4 (4)C14'—C13'—C16'—C17'158.1 (6)
C12—C13—C16—C1589.1 (5)C12'—C13'—C16'—C15'88.2 (5)
C14—O4—C21—O56.5 (8)C14'—C13'—C16'—C15'26.4 (5)
C14—O4—C21—C22175.3 (5)C14'—O4'—C21'—O5'4.0 (8)
C10'—C1'—C2'—C3'28.0 (14)C14'—O4'—C21'—C22'174.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O1i0.822.092.747 (6)137
O2—H2O···O1i0.822.092.747 (6)137
O2—H2O···O1i0.822.052.764 (5)146
O2—H2O···O1*i0.822.242.89 (3)136
Symmetry code: (i) x, y, z1.

Experimental details

Crystal data
Chemical formulaC22H30O5
Mr374.46
Crystal system, space groupMonoclinic, P21
Temperature (K)296
a, b, c (Å)8.485 (4), 23.786 (10), 9.930 (4)
β (°) 91.039 (17)
V3)2003.8 (15)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.36 × 0.34 × 0.32
Data collection
DiffractometerRigaku R-AXIS RAPID
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
19620, 4669, 2856
Rint0.070
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.164, 1.00
No. of reflections4669
No. of parameters524
No. of restraints14
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.19, 0.20

Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2O···O1i0.822.092.747 (6)136.8
O2—H2O···O1i0.822.092.747 (6)136.8
O2'—H2O'···O1'i0.822.052.764 (5)145.7
O2'—H2O'···O1*i0.822.242.89 (3)136.3
Symmetry code: (i) x, y, z1.
 

Acknowledgements

This work was supported by the Henan Province Science and Technology Foundation (grant No. 082300450440)

References

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First citationBai, S. P., Ma, X. K. & Zhang, J. X. (2005). J. Xinxiang Med. Coll. 22, 297–299.  CAS Google Scholar
First citationKim, D. S., Chang, R. G., Shen, X. Y., Chen, Y. P. & Sun, H. D. (1992). Phytochemistry, 31, 697–699.  CAS Google Scholar
First citationLiu, C. J., Zhao, Z. H., Wang, Q. R., Sun, H. D. & Lin, Z. W. (1988). Acta Bot. Yunnanica, 10, 471–473.  CAS Google Scholar
First citationRigaku (2004). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSun, H. D., Xu, Y. L. & Jiang, B. (2001). Diterpenoids from Isodon Species, pp. 4–17, 140. Beijing: Science Press.  Google Scholar

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