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

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ISSN: 2056-9890

15α,20β-Dihydr­­oxy-6β-meth­­oxy-6,7-seco-6,20-ep­­oxy-1,7-olide-ent-kaur-16-ene

aSchool of Pharmacy, Xinxiang Medical University, Xinxiang, Henan 453003, People's Republic of China
*Correspondence e-mail: yannz2009@163.com

(Received 23 February 2010; accepted 21 March 2010; online 27 March 2010)

The title compound, C21H30O6, a natural ent-kaurane diterpenoid, was obtained from the medicinal plant Isodon serra. The five rings in the mol­ecule exhibit the expected cis and trans junctions. The three six-membered rings adopt chair, twist-boat and boat conformations, while two five-membered rings adopt envelope conformations. There are two mol­ecules in the asymmetric unit, related by a non-crystallographic twofold screw axis; the main difference is in the different degrees of distortion of ring B. In the crystal, the mol­ecules are linked by inter­molecular O—H⋯O hydrogen bonds, forming chains along the b axis.

Related literature

For the genus Isodon and diterpenoids, see: Sun et al. (2001[Sun, H. D., Xu, Y. L. & Jiang, B. (2001). Diterpenoids from Isodon Species, pp. 4-17. Beijing: Science Press.]); Yan et al. (2007[Yan, F.-L., Zhang, L.-B., Zhang, J.-X. & Sun, H.-D. (2007). Chin. Chem. Lett. 18, 1383-1385.], 2008[Yan, F.-L., Guo, L.-Q., Bai, S.-P. & Sun, H.-D. (2008). J. Chin. Chem. Soc. 55, 933-936.]). For bond-length data, 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.]). For the structure of another ent-kaur-16-ene from an Isodon genus, see: Feng et al. (2010[Feng, C., Yan, F.-L., Di, X.-M. & Sun, P.-L. (2010). Acta Cryst. E66, o103.]).

[Scheme 1]

Experimental

Crystal data
  • C21H30O6

  • Mr = 378.45

  • Monoclinic, P 21

  • a = 13.145 (3) Å

  • b = 10.787 (2) Å

  • c = 14.074 (3) Å

  • β = 105.553 (3)°

  • V = 1922.6 (7) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.10 mm−1

  • T = 93 K

  • 0.60 × 0.55 × 0.55 mm

Data collection
  • Rigaku AFC10/Saturn724+ diffractometer

  • 15542 measured reflections

  • 4603 independent reflections

  • 4328 reflections with I > 2σ(I)

  • Rint = 0.030

Refinement
  • R[F2 > 2σ(F2)] = 0.032

  • wR(F2) = 0.079

  • S = 1.00

  • 4603 reflections

  • 509 parameters

  • 1 restraint

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.18 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O3—H30⋯O5 0.85 (3) 1.88 (3) 2.695 (2) 161 (2)
O3′—H30′⋯O5′ 0.88 (3) 2.01 (3) 2.806 (2) 150 (3)
O5—H50⋯O4′i 0.83 (3) 1.84 (3) 2.663 (2) 169 (3)
O5′—H50′⋯O1′ii 0.90 (3) 1.89 (3) 2.7663 (19) 165 (3)
Symmetry codes: (i) [-x+1, y+{\script{1\over 2}}, -z]; (ii) [-x+1, y-{\script{1\over 2}}, -z].

Data collection: CrystalClear (Rigaku/MSC, 2008[Rigaku/MSC (2008). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA.]); cell refinement: CrystalClear; data reduction: CrystalClear; 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: SHELXL97.

Supporting information


Comment top

The title compound, 15α,20β-dihydroxy-6β-methoxy-6,7-seco-6,20- epoxy-1,7-olide-ent-kaur-16-ene, C21H30O6 (I) is a natural ent-kaurane diterpenoid isolated from the medicinal plant Isodon serra which is widely distributed in China. The plant material is used for the treatment of acute jaundice, hepatitis and acute cholecystitis in folk medicine. We extracted the leaves of Isodon serra, collected in the Henan province of China and obtained the title compound, and its structure was postulated from spectroscopic methods (Yan et al., 2007). The X-ray crystallographic analysis confirms this proposed molecular structure (Fig. 1) and represents a second crystallographically characterized ent-kaur-16-ene compound isolated from Isodon plant material. The asymmetric unit of (I) contains two independent but similar molecules. In these there is a trans junction between ring A (C1—C5/C10) and ring B (C7—C10/C1/O2); cis junctions are present between ring B and ring C (C8/C9/C11—C14), ring C and ring E (C8/C13—C16), and ring A and ring D (C5/C6/O1/C20/C10). Ring A adopts a chair conformation, with an average torsion angle of 50.02 (2) °. Ring C adopts a boat conformation, while ring B adopts a twist boat conformation because of the presence of a carbonyl group. Ring D and ring E show envelope conformations. The two hydroxyl groups at C15 and C20 adopt α and β-orientations respectively, while the methoxy group at C6 adopts a β-orientation. Bond lengths and angles are within expected ranges (Allen et al., 1987), with average values (Å) in the first molecule: Csp3—Csp3 = 1.543 (3), Csp3—Csp2 = 1.524 (3), Csp2—Csp2 (CC) = 1.326 (2), Csp3—O = 1.424 (2), and Csp3—Csp3 = 1.545 (3), Csp3—Csp2 = 1.525 (3), Csp2—Csp2 (CC) = 1.324 (2), Csp3—O = 1.448 (2) in the second molecule.

Compound (I) contains eight chiral centers at C1(S), C5(R), C8(S), C9(S), C10(R), C13(R), C15(R), and C20(S). Although the absolute configuration could not be reliably determined from anomalous dispersion effects, the negative optical rotation shows this compound to be of the ent-kaurane series as reported for the genus Isodon (Sun et al., 2001), rather than of the kaurane series, allowing us to assign the correct configuration. In the crystal structure, intermolecular O—H···O hydrogen bonds (Table 1) are effective in the stabilization of the structure and are responsible for the formation of one-dimensional chains extending down the b axis of the unit cell (Fig. 2).

Related literature top

For the genus Isodon and diterpenoids, see: Sun et al. (2001); Yan et al. (2007, 2008). For bond-length data, see: Allen et al. (1987). For the structure of another ent-kaur-16-ene from an Isodon genus, see: Feng et al. (2010).

Experimental top

The dried and crushed leaves of Isodon serra (11 kg), collected from Henan Province, China, were extracted four times with Me2CO/H2O (7:3, v/v) at room temperature over a period of six days. The combined extract was filtered and the solvent was removed under reduced pressure. The extract was suspended in water and then partitioned successively with AcOEt, then concentrated to obtain a residue, which was then subjected to column chromatography over silica gel. Recrystallization from CHCl3/CH3OH (10:1), gave 55 mg of the title compound (m.p. 469-470 K; optical rotation: [α]D23 -141.0° (c 0.19, CH3OH). Crystals suitable for X-ray analysis were obtained by slow evaporation of a solution in CH3OH at room temperature.

Refinement top

All H atoms were included in calculated positions and refined as riding atoms, with C—H = 0.98Å (CH3), 0.99Å (CH2), and 1.00Å (CH), and with Uiso(H) = 1.2 Ueq(C). In the absence of significant anomalous scattering effects, Friedel pairs were merged. The choice of the enantiomer was based on comparison of the optical rotation with that of related compounds having known stereochemistry.

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2008); cell refinement: CrystalClear (Rigaku/MSC, 2008); data reduction: CrystalClear (Rigaku/MSC, 2008); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. Molecular configuration and atom numbering scheme for the two independent molecules of (I) in the asymmetric unit. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. The crystal packing of (I), viewed along the c axis of the unit cell, showing the O—H···O hydrogen bonds as dashed lines.
15α,20β-Dihydroxy-6β-methoxy-6,7-seco-6,20-epoxy-1,7-olide- ent-kaur-16-ene top
Crystal data top
C21H30O6F(000) = 816
Mr = 378.45Dx = 1.308 Mg m3
Monoclinic, P21Melting point = 479–470 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 13.145 (3) ÅCell parameters from 6766 reflections
b = 10.787 (2) Åθ = 3.0–27.5°
c = 14.074 (3) ŵ = 0.10 mm1
β = 105.553 (3)°T = 93 K
V = 1922.6 (7) Å3Block, colorless
Z = 40.60 × 0.55 × 0.55 mm
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
4328 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.030
Graphite monochromatorθmax = 27.5°, θmin = 3.0°
Detector resolution: 28.5714 pixels mm-1h = 1713
multi–scank = 1311
15542 measured reflectionsl = 1818
4603 independent reflections
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)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.048P)2 + 0.166P]
where P = (Fo2 + 2Fc2)/3
4603 reflections(Δ/σ)max = 0.001
509 parametersΔρmax = 0.28 e Å3
1 restraintΔρmin = 0.18 e Å3
Crystal data top
C21H30O6V = 1922.6 (7) Å3
Mr = 378.45Z = 4
Monoclinic, P21Mo Kα radiation
a = 13.145 (3) ŵ = 0.10 mm1
b = 10.787 (2) ÅT = 93 K
c = 14.074 (3) Å0.60 × 0.55 × 0.55 mm
β = 105.553 (3)°
Data collection top
Rigaku AFC10/Saturn724+
diffractometer
4328 reflections with I > 2σ(I)
15542 measured reflectionsRint = 0.030
4603 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0321 restraint
wR(F2) = 0.079H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.28 e Å3
4603 reflectionsΔρmin = 0.18 e Å3
509 parameters
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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*/Ueq
O10.21535 (10)0.59129 (13)0.25270 (9)0.0183 (3)
O20.04936 (10)0.81341 (13)0.41597 (10)0.0167 (3)
O30.10251 (11)0.76108 (13)0.22402 (9)0.0176 (3)
O40.01659 (10)0.98946 (13)0.33514 (9)0.0175 (3)
O50.22703 (11)0.96108 (14)0.23065 (10)0.0202 (3)
O60.39423 (10)0.61812 (13)0.33706 (9)0.0176 (3)
C10.12818 (14)0.72142 (18)0.46303 (13)0.0155 (4)
H10.17160.75720.52650.019*
C20.06994 (15)0.61002 (19)0.48695 (15)0.0206 (4)
H2A0.02060.57760.42600.025*
H2B0.02860.63380.53340.025*
C30.15069 (15)0.51062 (19)0.53337 (15)0.0209 (4)
H3A0.11380.44000.55440.025*
H3B0.20100.54520.59290.025*
C40.21236 (15)0.46348 (19)0.46194 (14)0.0181 (4)
C50.26792 (14)0.57554 (17)0.42642 (13)0.0146 (4)
H50.33270.59670.47990.018*
C60.30092 (14)0.55038 (18)0.33222 (13)0.0161 (4)
H60.31360.45970.32570.019*
C70.08214 (14)0.91506 (18)0.37685 (12)0.0140 (4)
C80.20072 (14)0.93549 (18)0.39484 (13)0.0139 (4)
C90.26956 (14)0.81465 (18)0.40115 (13)0.0134 (3)
H90.29690.81350.34140.016*
C100.20151 (13)0.69580 (17)0.39725 (13)0.0135 (4)
C110.36637 (14)0.81940 (18)0.49186 (13)0.0162 (4)
H11A0.34290.80260.55190.019*
H11B0.41620.75290.48590.019*
C120.42462 (15)0.94401 (19)0.50428 (15)0.0207 (4)
H12A0.47220.94580.46040.025*
H12B0.46880.95140.57310.025*
C130.34882 (15)1.05648 (18)0.48017 (14)0.0181 (4)
H130.37691.12880.52380.022*
C140.23949 (15)1.01650 (19)0.48929 (13)0.0171 (4)
H14A0.19271.08870.48820.021*
H14B0.24490.96760.55000.021*
C150.22230 (14)1.02618 (18)0.31723 (13)0.0152 (4)
H150.16391.08850.29960.018*
C160.32415 (14)1.09148 (19)0.37185 (14)0.0173 (4)
C170.37885 (16)1.1670 (2)0.32979 (15)0.0233 (4)
H17A0.44101.20580.36860.028*
H17B0.35581.18220.26080.028*
C180.29977 (15)0.37646 (19)0.52032 (15)0.0203 (4)
H18A0.34340.42050.57780.024*
H18B0.34390.34980.47800.024*
H18C0.26760.30370.54230.024*
C190.13931 (16)0.38538 (19)0.37930 (16)0.0234 (4)
H19A0.11300.31380.40840.028*
H19B0.17900.35660.33370.028*
H19C0.07960.43630.34340.028*
C200.14130 (14)0.66459 (18)0.28865 (13)0.0146 (4)
H200.08040.60980.29040.018*
C210.43104 (16)0.6056 (2)0.25089 (15)0.0280 (5)
H21A0.43470.51750.23510.034*
H21B0.50140.64260.26300.034*
H21C0.38230.64800.19550.034*
O1'0.61754 (10)1.02618 (13)0.02824 (9)0.0193 (3)
O2'0.83569 (11)0.76955 (13)0.03698 (10)0.0198 (3)
O3'0.60905 (11)0.83925 (14)0.05461 (10)0.0207 (3)
O4'0.74557 (12)0.59810 (15)0.08204 (10)0.0255 (3)
O5'0.56677 (11)0.64907 (14)0.06543 (10)0.0214 (3)
O6'0.64390 (10)1.01648 (14)0.19995 (10)0.0214 (3)
C1'0.86959 (15)0.86529 (18)0.03932 (14)0.0171 (4)
H1'0.92280.82760.09650.021*
C2'0.92367 (15)0.9662 (2)0.00343 (15)0.0218 (4)
H2C'0.87540.99860.06500.026*
H2D'0.98740.93280.01910.026*
C3'0.95441 (15)1.0701 (2)0.07316 (15)0.0226 (4)
H3C'0.99571.13350.04880.027*
H3D'1.00011.03550.13520.027*
C4'0.85739 (15)1.13206 (19)0.09477 (14)0.0198 (4)
C5'0.79168 (14)1.03008 (18)0.13136 (13)0.0153 (4)
H5'0.82701.01230.20230.018*
C6'0.67826 (14)1.07021 (19)0.12311 (13)0.0176 (4)
H6'0.67391.16260.12620.021*
C7'0.77627 (15)0.67684 (19)0.01898 (14)0.0185 (4)
C8'0.75785 (14)0.66697 (18)0.08296 (13)0.0140 (4)
C9'0.74751 (14)0.79359 (17)0.13467 (13)0.0132 (4)
H9'0.67200.80260.13550.016*
C10'0.77399 (14)0.90470 (18)0.07427 (13)0.0138 (4)
C11'0.81477 (14)0.79157 (18)0.24275 (13)0.0152 (4)
H11C0.89020.80050.24450.018*
H11D0.79510.86300.27830.018*
C12'0.79969 (15)0.67141 (19)0.29529 (13)0.0170 (4)
H12C0.73010.67380.30990.020*
H12D0.85470.66640.35890.020*
C13'0.80568 (14)0.55338 (18)0.23381 (13)0.0164 (4)
H13'0.84730.48590.27530.020*
C14'0.85067 (14)0.58773 (19)0.14703 (13)0.0167 (4)
H14C0.86420.51320.11120.020*
H14D0.91640.63680.16910.020*
C15'0.66278 (14)0.57987 (19)0.08060 (14)0.0168 (4)
H15'0.65520.51900.02550.020*
C16'0.69535 (14)0.51043 (19)0.17910 (14)0.0173 (4)
C17'0.63873 (16)0.4233 (2)0.20734 (15)0.0227 (4)
H17C0.66670.38050.26770.027*
H17D0.57020.40370.16730.027*
C18'0.89630 (17)1.2245 (2)0.18054 (16)0.0249 (4)
H18D0.94061.18080.23790.030*
H18E0.83541.26110.19790.030*
H18F0.93761.29020.16030.030*
C19'0.79649 (17)1.2062 (2)0.00367 (16)0.0244 (4)
H19D0.73521.24640.01770.029*
H19E0.77251.15000.05260.029*
H19F0.84301.26950.01210.029*
C20'0.67574 (14)0.93572 (18)0.01246 (13)0.0164 (4)
H20'0.70090.97700.06560.020*
C21'0.53768 (18)1.0486 (3)0.19681 (18)0.0343 (6)
H21D0.52901.13870.19090.041*
H21E0.52181.02050.25750.041*
H21F0.48931.00850.13990.041*
H300.1504 (19)0.812 (2)0.2211 (17)0.022 (6)*
H500.2315 (19)1.011 (3)0.1869 (19)0.028 (7)*
H30'0.586 (2)0.803 (3)0.009 (2)0.043 (8)*
H50'0.514 (2)0.598 (3)0.035 (2)0.049 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0177 (6)0.0204 (7)0.0149 (6)0.0048 (6)0.0010 (5)0.0037 (5)
O20.0141 (6)0.0168 (7)0.0210 (6)0.0026 (5)0.0077 (5)0.0051 (5)
O30.0163 (6)0.0180 (7)0.0164 (6)0.0010 (6)0.0009 (5)0.0029 (5)
O40.0153 (6)0.0179 (7)0.0188 (6)0.0032 (5)0.0036 (5)0.0025 (5)
O50.0291 (8)0.0181 (8)0.0136 (6)0.0051 (6)0.0064 (6)0.0012 (6)
O60.0161 (6)0.0206 (8)0.0174 (6)0.0010 (5)0.0067 (5)0.0003 (5)
C10.0138 (8)0.0164 (9)0.0167 (8)0.0036 (7)0.0049 (7)0.0036 (7)
C20.0182 (9)0.0196 (11)0.0268 (10)0.0031 (8)0.0107 (8)0.0068 (8)
C30.0189 (9)0.0185 (11)0.0269 (10)0.0019 (8)0.0088 (8)0.0088 (8)
C40.0168 (9)0.0153 (10)0.0222 (9)0.0002 (7)0.0052 (7)0.0041 (7)
C50.0141 (8)0.0128 (10)0.0160 (8)0.0015 (7)0.0025 (7)0.0002 (7)
C60.0142 (8)0.0153 (10)0.0172 (8)0.0015 (7)0.0017 (7)0.0000 (7)
C70.0155 (8)0.0149 (10)0.0122 (7)0.0007 (7)0.0047 (7)0.0011 (7)
C80.0150 (8)0.0129 (9)0.0132 (8)0.0007 (7)0.0029 (6)0.0006 (7)
C90.0131 (8)0.0127 (9)0.0130 (7)0.0023 (7)0.0012 (6)0.0001 (7)
C100.0115 (8)0.0145 (10)0.0140 (8)0.0009 (7)0.0025 (7)0.0013 (7)
C110.0133 (8)0.0174 (10)0.0158 (8)0.0010 (7)0.0002 (7)0.0004 (7)
C120.0157 (9)0.0167 (10)0.0254 (9)0.0012 (8)0.0018 (7)0.0022 (8)
C130.0180 (9)0.0149 (10)0.0192 (9)0.0011 (7)0.0013 (7)0.0029 (7)
C140.0192 (9)0.0164 (10)0.0144 (8)0.0022 (8)0.0023 (7)0.0023 (7)
C150.0156 (8)0.0136 (9)0.0158 (8)0.0005 (7)0.0033 (7)0.0011 (7)
C160.0160 (8)0.0157 (10)0.0200 (9)0.0008 (7)0.0042 (7)0.0033 (7)
C170.0217 (9)0.0251 (11)0.0240 (9)0.0063 (9)0.0076 (8)0.0045 (9)
C180.0200 (9)0.0158 (10)0.0253 (10)0.0020 (8)0.0066 (8)0.0049 (8)
C190.0217 (10)0.0146 (10)0.0311 (11)0.0031 (8)0.0024 (8)0.0029 (8)
C200.0142 (8)0.0133 (9)0.0156 (8)0.0002 (7)0.0024 (7)0.0002 (7)
C210.0233 (10)0.0427 (14)0.0205 (9)0.0012 (10)0.0106 (8)0.0015 (9)
O1'0.0156 (6)0.0206 (7)0.0193 (6)0.0059 (6)0.0008 (5)0.0019 (6)
O2'0.0231 (7)0.0197 (7)0.0181 (6)0.0019 (6)0.0082 (5)0.0013 (5)
O3'0.0186 (7)0.0220 (8)0.0183 (7)0.0001 (6)0.0008 (5)0.0018 (6)
O4'0.0321 (8)0.0250 (8)0.0194 (7)0.0013 (7)0.0070 (6)0.0073 (6)
O5'0.0118 (6)0.0189 (8)0.0294 (7)0.0001 (5)0.0014 (5)0.0013 (6)
O6'0.0188 (7)0.0240 (8)0.0227 (7)0.0052 (6)0.0078 (5)0.0011 (6)
C1'0.0172 (9)0.0176 (10)0.0169 (9)0.0024 (7)0.0052 (7)0.0003 (7)
C2'0.0193 (9)0.0229 (11)0.0251 (10)0.0016 (8)0.0095 (8)0.0045 (8)
C3'0.0167 (9)0.0234 (11)0.0275 (10)0.0025 (8)0.0055 (8)0.0067 (8)
C4'0.0190 (9)0.0158 (10)0.0221 (9)0.0012 (8)0.0013 (7)0.0029 (8)
C5'0.0149 (8)0.0135 (9)0.0163 (8)0.0019 (7)0.0021 (7)0.0003 (7)
C6'0.0185 (9)0.0161 (10)0.0172 (9)0.0027 (7)0.0027 (7)0.0018 (7)
C7'0.0179 (9)0.0194 (10)0.0184 (9)0.0062 (8)0.0050 (7)0.0023 (8)
C8'0.0135 (8)0.0132 (9)0.0141 (8)0.0015 (7)0.0017 (6)0.0016 (7)
C9'0.0133 (8)0.0129 (9)0.0121 (8)0.0009 (7)0.0013 (6)0.0011 (7)
C10'0.0131 (8)0.0139 (9)0.0134 (8)0.0010 (7)0.0019 (7)0.0001 (7)
C11'0.0154 (8)0.0153 (10)0.0127 (8)0.0004 (7)0.0001 (7)0.0012 (7)
C12'0.0172 (8)0.0179 (10)0.0142 (8)0.0000 (7)0.0015 (7)0.0016 (7)
C13'0.0159 (8)0.0146 (10)0.0173 (8)0.0001 (7)0.0018 (7)0.0014 (7)
C14'0.0154 (8)0.0147 (9)0.0187 (9)0.0036 (7)0.0022 (7)0.0007 (7)
C15'0.0147 (8)0.0148 (10)0.0192 (9)0.0007 (7)0.0015 (7)0.0037 (7)
C16'0.0164 (8)0.0157 (10)0.0193 (9)0.0015 (7)0.0038 (7)0.0035 (7)
C17'0.0206 (10)0.0219 (11)0.0243 (9)0.0014 (8)0.0037 (8)0.0012 (8)
C18'0.0254 (10)0.0162 (10)0.0287 (10)0.0025 (9)0.0005 (8)0.0006 (8)
C19'0.0235 (10)0.0193 (11)0.0284 (10)0.0001 (8)0.0033 (8)0.0074 (8)
C20'0.0151 (9)0.0182 (10)0.0146 (8)0.0039 (7)0.0019 (7)0.0001 (7)
C21'0.0265 (11)0.0436 (15)0.0377 (12)0.0112 (10)0.0173 (10)0.0071 (11)
Geometric parameters (Å, º) top
O1—C61.427 (2)O1'—C6'1.440 (2)
O1—C201.447 (2)O1'—C20'1.449 (2)
O2—C71.348 (2)O2'—C7'1.334 (2)
O2—C11.459 (2)O2'—C1'1.470 (2)
O3—C201.386 (2)O3'—C20'1.387 (2)
O3—H300.85 (3)O3'—H30'0.88 (3)
O4—C71.208 (2)O4'—C7'1.216 (2)
O5—C151.422 (2)O5'—C15'1.432 (2)
O5—H500.83 (3)O5'—H50'0.90 (3)
O6—C61.414 (2)O6'—C6'1.404 (2)
O6—C211.428 (2)O6'—C21'1.428 (2)
C1—C21.511 (3)C1'—C2'1.510 (3)
C1—C101.530 (2)C1'—C10'1.528 (3)
C1—H11.0000C1'—H1'1.0000
C2—C31.527 (3)C2'—C3'1.532 (3)
C2—H2A0.9900C2'—H2C'0.9900
C2—H2B0.9900C2'—H2D'0.9900
C3—C41.537 (3)C3'—C4'1.541 (3)
C3—H3A0.9900C3'—H3C'0.9900
C3—H3B0.9900C3'—H3D'0.9900
C4—C181.540 (3)C4'—C19'1.541 (3)
C4—C191.545 (3)C4'—C18'1.543 (3)
C4—C51.562 (3)C4'—C5'1.568 (3)
C5—C61.526 (3)C5'—C6'1.527 (2)
C5—C101.556 (3)C5'—C10'1.558 (3)
C5—H51.0000C5'—H5'1.0000
C6—H61.0000C6'—H6'1.0000
C7—C81.527 (2)C7'—C8'1.521 (3)
C8—C151.548 (3)C8'—C15'1.557 (3)
C8—C141.558 (2)C8'—C14'1.563 (2)
C8—C91.576 (3)C8'—C9'1.571 (3)
C9—C111.543 (2)C9'—C11'1.541 (2)
C9—C101.556 (3)C9'—C10'1.562 (3)
C9—H91.0000C9'—H9'1.0000
C10—C201.558 (2)C10'—C20'1.557 (2)
C11—C121.534 (3)C11'—C12'1.531 (3)
C11—H11A0.9900C11'—H11C0.9900
C11—H11B0.9900C11'—H11D0.9900
C12—C131.549 (3)C12'—C13'1.553 (3)
C12—H12A0.9900C12'—H12C0.9900
C12—H12B0.9900C12'—H12D0.9900
C13—C161.519 (3)C13'—C16'1.521 (3)
C13—C141.538 (3)C13'—C14'1.538 (3)
C13—H131.0000C13'—H13'1.0000
C14—H14A0.9900C14'—H14C0.9900
C14—H14B0.9900C14'—H14D0.9900
C15—C161.526 (3)C15'—C16'1.532 (3)
C15—H151.0000C15'—H15'1.0000
C16—C171.326 (3)C16'—C17'1.324 (3)
C17—H17A0.9500C17'—H17C0.9500
C17—H17B0.9500C17'—H17D0.9500
C18—H18A0.9800C18'—H18D0.9800
C18—H18B0.9800C18'—H18E0.9800
C18—H18C0.9800C18'—H18F0.9800
C19—H19A0.9800C19'—H19D0.9800
C19—H19B0.9800C19'—H19E0.9800
C19—H19C0.9800C19'—H19F0.9800
C20—H201.0000C20'—H20'1.0000
C21—H21A0.9800C21'—H21D0.9800
C21—H21B0.9800C21'—H21E0.9800
C21—H21C0.9800C21'—H21F0.9800
C6—O1—C20110.95 (13)C6'—O1'—C20'111.62 (13)
C7—O2—C1118.20 (14)C7'—O2'—C1'117.78 (14)
C20—O3—H30111.9 (16)C20'—O3'—H30'109 (2)
C15—O5—H50110.0 (18)C15'—O5'—H50'107 (2)
C6—O6—C21113.42 (15)C6'—O6'—C21'112.95 (15)
O2—C1—C2107.55 (14)O2'—C1'—C2'107.35 (15)
O2—C1—C10109.52 (14)O2'—C1'—C10'108.44 (15)
C2—C1—C10115.49 (16)C2'—C1'—C10'116.32 (16)
O2—C1—H1108.0O2'—C1'—H1'108.2
C2—C1—H1108.0C2'—C1'—H1'108.2
C10—C1—H1108.0C10'—C1'—H1'108.2
C1—C2—C3108.56 (15)C1'—C2'—C3'108.08 (16)
C1—C2—H2A110.0C1'—C2'—H2C'110.1
C3—C2—H2A110.0C3'—C2'—H2C'110.1
C1—C2—H2B110.0C1'—C2'—H2D'110.1
C3—C2—H2B110.0C3'—C2'—H2D'110.1
H2A—C2—H2B108.4H2C'—C2'—H2D'108.4
C2—C3—C4112.37 (16)C2'—C3'—C4'112.34 (16)
C2—C3—H3A109.1C2'—C3'—H3C'109.1
C4—C3—H3A109.1C4'—C3'—H3C'109.1
C2—C3—H3B109.1C2'—C3'—H3D'109.1
C4—C3—H3B109.1C4'—C3'—H3D'109.1
H3A—C3—H3B107.9H3C'—C3'—H3D'107.9
C3—C4—C18107.56 (15)C19'—C4'—C3'109.51 (17)
C3—C4—C19110.03 (16)C19'—C4'—C18'107.74 (17)
C18—C4—C19107.07 (16)C3'—C4'—C18'108.45 (16)
C3—C4—C5109.09 (16)C19'—C4'—C5'115.36 (16)
C18—C4—C5107.25 (15)C3'—C4'—C5'108.56 (16)
C19—C4—C5115.51 (16)C18'—C4'—C5'107.00 (16)
C6—C5—C10100.90 (14)C6'—C5'—C10'101.50 (14)
C6—C5—C4114.00 (15)C6'—C5'—C4'112.87 (15)
C10—C5—C4116.88 (14)C10'—C5'—C4'117.29 (15)
C6—C5—H5108.2C6'—C5'—H5'108.2
C10—C5—H5108.2C10'—C5'—H5'108.2
C4—C5—H5108.2C4'—C5'—H5'108.2
O6—C6—O1111.67 (15)O6'—C6'—O1'111.42 (15)
O6—C6—C5108.14 (15)O6'—C6'—C5'109.49 (15)
O1—C6—C5106.17 (14)O1'—C6'—C5'105.31 (14)
O6—C6—H6110.3O6'—C6'—H6'110.2
O1—C6—H6110.3O1'—C6'—H6'110.2
C5—C6—H6110.3C5'—C6'—H6'110.2
O4—C7—O2118.31 (16)O4'—C7'—O2'118.78 (17)
O4—C7—C8123.23 (17)O4'—C7'—C8'122.24 (18)
O2—C7—C8118.26 (15)O2'—C7'—C8'118.74 (16)
C7—C8—C15110.26 (14)C7'—C8'—C15'110.61 (15)
C7—C8—C14107.96 (14)C7'—C8'—C14'106.58 (14)
C15—C8—C1499.65 (15)C15'—C8'—C14'100.39 (15)
C7—C8—C9115.81 (15)C7'—C8'—C9'115.56 (15)
C15—C8—C9110.57 (14)C15'—C8'—C9'111.47 (15)
C14—C8—C9111.37 (14)C14'—C8'—C9'111.07 (14)
C11—C9—C10113.29 (15)C11'—C9'—C10'113.29 (15)
C11—C9—C8110.67 (15)C11'—C9'—C8'110.31 (15)
C10—C9—C8111.33 (14)C10'—C9'—C8'110.83 (14)
C11—C9—H9107.1C11'—C9'—H9'107.4
C10—C9—H9107.1C10'—C9'—H9'107.4
C8—C9—H9107.1C8'—C9'—H9'107.4
C1—C10—C9106.22 (15)C1'—C10'—C20'112.86 (15)
C1—C10—C5113.00 (15)C1'—C10'—C5'112.69 (15)
C9—C10—C5113.65 (14)C20'—C10'—C5'101.27 (14)
C1—C10—C20113.33 (14)C1'—C10'—C9'106.52 (15)
C9—C10—C20110.41 (14)C20'—C10'—C9'109.42 (15)
C5—C10—C20100.38 (14)C5'—C10'—C9'114.18 (14)
C12—C11—C9113.53 (16)C12'—C11'—C9'111.98 (15)
C12—C11—H11A108.9C12'—C11'—H11C109.2
C9—C11—H11A108.9C9'—C11'—H11C109.2
C12—C11—H11B108.9C12'—C11'—H11D109.2
C9—C11—H11B108.9C9'—C11'—H11D109.2
H11A—C11—H11B107.7H11C—C11'—H11D107.9
C11—C12—C13112.92 (15)C11'—C12'—C13'113.10 (14)
C11—C12—H12A109.0C11'—C12'—H12C109.0
C13—C12—H12A109.0C13'—C12'—H12C109.0
C11—C12—H12B109.0C11'—C12'—H12D109.0
C13—C12—H12B109.0C13'—C12'—H12D109.0
H12A—C12—H12B107.8H12C—C12'—H12D107.8
C16—C13—C14101.58 (14)C16'—C13'—C14'100.89 (14)
C16—C13—C12111.49 (16)C16'—C13'—C12'110.36 (15)
C14—C13—C12108.82 (16)C14'—C13'—C12'109.43 (15)
C16—C13—H13111.5C16'—C13'—H13'111.9
C14—C13—H13111.5C14'—C13'—H13'111.9
C12—C13—H13111.5C12'—C13'—H13'111.9
C13—C14—C8100.67 (14)C13'—C14'—C8'100.54 (14)
C13—C14—H14A111.6C13'—C14'—H14C111.7
C8—C14—H14A111.6C8'—C14'—H14C111.7
C13—C14—H14B111.6C13'—C14'—H14D111.7
C8—C14—H14B111.6C8'—C14'—H14D111.7
H14A—C14—H14B109.4H14C—C14'—H14D109.4
O5—C15—C16115.19 (15)O5'—C15'—C16'114.27 (15)
O5—C15—C8110.54 (15)O5'—C15'—C8'111.03 (16)
C16—C15—C8103.79 (14)C16'—C15'—C8'104.35 (14)
O5—C15—H15109.0O5'—C15'—H15'109.0
C16—C15—H15109.0C16'—C15'—H15'109.0
C8—C15—H15109.0C8'—C15'—H15'109.0
C17—C16—C13127.25 (18)C17'—C16'—C13'126.92 (18)
C17—C16—C15124.48 (17)C17'—C16'—C15'125.12 (17)
C13—C16—C15108.26 (15)C13'—C16'—C15'107.84 (15)
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
O3—C20—O1110.15 (14)O3'—C20'—O1'109.51 (14)
O3—C20—C10118.82 (16)O3'—C20'—C10'118.05 (16)
O1—C20—C10104.41 (13)O1'—C20'—C10'104.46 (14)
O3—C20—H20107.7O3'—C20'—H20'108.1
O1—C20—H20107.7O1'—C20'—H20'108.1
C10—C20—H20107.7C10'—C20'—H20'108.1
O6—C21—H21A109.5O6'—C21'—H21D109.5
O6—C21—H21B109.5O6'—C21'—H21E109.5
H21A—C21—H21B109.5H21D—C21'—H21E109.5
O6—C21—H21C109.5O6'—C21'—H21F109.5
H21A—C21—H21C109.5H21D—C21'—H21F109.5
H21B—C21—H21C109.5H21E—C21'—H21F109.5
C7—O2—C1—C2171.93 (15)C7'—O2'—C1'—C2'173.29 (15)
C7—O2—C1—C1045.7 (2)C7'—O2'—C1'—C10'46.9 (2)
O2—C1—C2—C3178.22 (15)O2'—C1'—C2'—C3'177.07 (15)
C10—C1—C2—C355.6 (2)C10'—C1'—C2'—C3'55.5 (2)
C1—C2—C3—C463.5 (2)C1'—C2'—C3'—C4'63.9 (2)
C2—C3—C4—C18173.19 (16)C2'—C3'—C4'—C19'69.0 (2)
C2—C3—C4—C1970.5 (2)C2'—C3'—C4'—C18'173.70 (16)
C2—C3—C4—C557.2 (2)C2'—C3'—C4'—C5'57.8 (2)
C3—C4—C5—C6161.07 (15)C19'—C4'—C5'—C6'38.0 (2)
C18—C4—C5—C682.71 (19)C3'—C4'—C5'—C6'161.32 (15)
C19—C4—C5—C636.6 (2)C18'—C4'—C5'—C6'81.82 (18)
C3—C4—C5—C1043.8 (2)C19'—C4'—C5'—C10'79.4 (2)
C18—C4—C5—C10160.05 (15)C3'—C4'—C5'—C10'43.9 (2)
C19—C4—C5—C1080.7 (2)C18'—C4'—C5'—C10'160.72 (15)
C21—O6—C6—O161.4 (2)C21'—O6'—C6'—O1'63.3 (2)
C21—O6—C6—C5177.86 (16)C21'—O6'—C6'—C5'179.37 (17)
C20—O1—C6—O6105.03 (17)C20'—O1'—C6'—O6'103.68 (17)
C20—O1—C6—C512.6 (2)C20'—O1'—C6'—C5'14.9 (2)
C10—C5—C6—O686.38 (16)C10'—C5'—C6'—O6'86.15 (17)
C4—C5—C6—O6147.48 (15)C4'—C5'—C6'—O6'147.43 (16)
C10—C5—C6—O133.58 (18)C10'—C5'—C6'—O1'33.75 (18)
C4—C5—C6—O192.56 (18)C4'—C5'—C6'—O1'92.67 (18)
C1—O2—C7—O4177.72 (16)C1'—O2'—C7'—O4'178.48 (17)
C1—O2—C7—C87.2 (2)C1'—O2'—C7'—C8'7.1 (2)
O4—C7—C8—C1525.1 (2)O4'—C7'—C8'—C15'22.4 (3)
O2—C7—C8—C15160.11 (15)O2'—C7'—C8'—C15'163.40 (16)
O4—C7—C8—C1482.8 (2)O4'—C7'—C8'—C14'85.9 (2)
O2—C7—C8—C1491.99 (19)O2'—C7'—C8'—C14'88.37 (19)
O4—C7—C8—C9151.57 (17)O4'—C7'—C8'—C9'150.20 (18)
O2—C7—C8—C933.6 (2)O2'—C7'—C8'—C9'35.6 (2)
C7—C8—C9—C11132.33 (16)C7'—C8'—C9'—C11'134.01 (16)
C15—C8—C9—C11101.34 (17)C15'—C8'—C9'—C11'98.59 (17)
C14—C8—C9—C118.5 (2)C14'—C8'—C9'—C11'12.5 (2)
C7—C8—C9—C105.4 (2)C7'—C8'—C9'—C10'7.7 (2)
C15—C8—C9—C10131.72 (15)C15'—C8'—C9'—C10'135.12 (15)
C14—C8—C9—C10118.45 (16)C14'—C8'—C9'—C10'113.84 (16)
O2—C1—C10—C970.23 (17)O2'—C1'—C10'—C20'49.3 (2)
C2—C1—C10—C9168.21 (15)C2'—C1'—C10'—C20'71.7 (2)
O2—C1—C10—C5164.51 (14)O2'—C1'—C10'—C5'163.28 (14)
C2—C1—C10—C542.9 (2)C2'—C1'—C10'—C5'42.3 (2)
O2—C1—C10—C2051.2 (2)O2'—C1'—C10'—C9'70.76 (17)
C2—C1—C10—C2070.4 (2)C2'—C1'—C10'—C9'168.20 (15)
C11—C9—C10—C183.26 (17)C6'—C5'—C10'—C1'159.79 (15)
C8—C9—C10—C142.23 (18)C4'—C5'—C10'—C1'36.3 (2)
C11—C9—C10—C541.6 (2)C6'—C5'—C10'—C20'38.96 (17)
C8—C9—C10—C5167.09 (14)C4'—C5'—C10'—C20'84.50 (18)
C11—C9—C10—C20153.49 (15)C6'—C5'—C10'—C9'78.50 (17)
C8—C9—C10—C2081.02 (17)C4'—C5'—C10'—C9'158.05 (15)
C6—C5—C10—C1161.27 (15)C11'—C9'—C10'—C1'83.32 (18)
C4—C5—C10—C137.1 (2)C8'—C9'—C10'—C1'41.29 (18)
C6—C5—C10—C977.59 (17)C11'—C9'—C10'—C20'154.39 (15)
C4—C5—C10—C9158.22 (15)C8'—C9'—C10'—C20'81.00 (18)
C6—C5—C10—C2040.27 (16)C11'—C9'—C10'—C5'41.7 (2)
C4—C5—C10—C2083.92 (18)C8'—C9'—C10'—C5'166.34 (15)
C10—C9—C11—C12171.65 (15)C10'—C9'—C11'—C12'170.93 (15)
C8—C9—C11—C1245.8 (2)C8'—C9'—C11'—C12'46.0 (2)
C9—C11—C12—C1339.6 (2)C9'—C11'—C12'—C13'46.8 (2)
C11—C12—C13—C1689.7 (2)C11'—C12'—C13'—C16'97.08 (18)
C11—C12—C13—C1421.6 (2)C11'—C12'—C13'—C14'13.1 (2)
C16—C13—C14—C844.46 (17)C16'—C13'—C14'—C8'47.58 (17)
C12—C13—C14—C873.24 (17)C12'—C13'—C14'—C8'68.75 (17)
C7—C8—C14—C13165.39 (15)C7'—C8'—C14'—C13'163.99 (15)
C15—C8—C14—C1350.28 (16)C15'—C8'—C14'—C13'48.65 (16)
C9—C8—C14—C1366.42 (17)C9'—C8'—C14'—C13'69.34 (17)
C7—C8—C15—O586.24 (18)C7'—C8'—C15'—O5'93.50 (18)
C14—C8—C15—O5160.42 (14)C14'—C8'—C15'—O5'154.24 (14)
C9—C8—C15—O543.12 (19)C9'—C8'—C15'—O5'36.5 (2)
C7—C8—C15—C16149.71 (15)C7'—C8'—C15'—C16'142.94 (15)
C14—C8—C15—C1636.37 (17)C14'—C8'—C15'—C16'30.68 (17)
C9—C8—C15—C1680.93 (17)C9'—C8'—C15'—C16'87.02 (17)
C14—C13—C16—C17157.1 (2)C14'—C13'—C16'—C17'147.5 (2)
C12—C13—C16—C1787.1 (2)C12'—C13'—C16'—C17'96.8 (2)
C14—C13—C16—C1521.86 (19)C14'—C13'—C16'—C15'28.65 (19)
C12—C13—C16—C1593.90 (18)C12'—C13'—C16'—C15'86.99 (18)
O5—C15—C16—C1750.6 (3)O5'—C15'—C16'—C17'60.7 (3)
C8—C15—C16—C17171.54 (19)C8'—C15'—C16'—C17'177.91 (19)
O5—C15—C16—C13130.43 (17)O5'—C15'—C16'—C13'123.06 (17)
C8—C15—C16—C139.46 (19)C8'—C15'—C16'—C13'1.6 (2)
C6—O1—C20—O3142.68 (15)C6'—O1'—C20'—O3'137.92 (15)
C6—O1—C20—C1014.04 (19)C6'—O1'—C20'—C10'10.58 (19)
C1—C10—C20—O382.1 (2)C1'—C10'—C20'—O3'86.5 (2)
C9—C10—C20—O336.9 (2)C5'—C10'—C20'—O3'152.74 (16)
C5—C10—C20—O3157.09 (15)C9'—C10'—C20'—O3'31.9 (2)
C1—C10—C20—O1154.68 (15)C1'—C10'—C20'—O1'151.57 (15)
C9—C10—C20—O186.31 (17)C5'—C10'—C20'—O1'30.85 (17)
C5—C10—C20—O133.90 (17)C9'—C10'—C20'—O1'90.02 (17)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H30···O50.85 (3)1.88 (3)2.695 (2)161 (2)
O3—H30···O50.88 (3)2.01 (3)2.806 (2)150 (3)
O5—H50···O4i0.83 (3)1.84 (3)2.663 (2)169 (3)
O5—H50···O1ii0.90 (3)1.89 (3)2.7663 (19)165 (3)
Symmetry codes: (i) x+1, y+1/2, z; (ii) x+1, y1/2, z.

Experimental details

Crystal data
Chemical formulaC21H30O6
Mr378.45
Crystal system, space groupMonoclinic, P21
Temperature (K)93
a, b, c (Å)13.145 (3), 10.787 (2), 14.074 (3)
β (°) 105.553 (3)
V3)1922.6 (7)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.60 × 0.55 × 0.55
Data collection
DiffractometerRigaku AFC10/Saturn724+
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15542, 4603, 4328
Rint0.030
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.032, 0.079, 1.00
No. of reflections4603
No. of parameters509
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.28, 0.18

Computer programs: CrystalClear (Rigaku/MSC, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O3—H30···O50.85 (3)1.88 (3)2.695 (2)161 (2)
O3'—H30'···O5'0.88 (3)2.01 (3)2.806 (2)150 (3)
O5—H50···O4'i0.83 (3)1.84 (3)2.663 (2)169 (3)
O5'—H50'···O1'ii0.90 (3)1.89 (3)2.7663 (19)165 (3)
Symmetry codes: (i) x+1, y+1/2, z; (ii) x+1, y1/2, z.
 

Acknowledgements

This work was supported by the Henan Province Science and Technology Foundation of China (No. 102102310011).

References

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First citationSun, H. D., Xu, Y. L. & Jiang, B. (2001). Diterpenoids from Isodon Species, pp. 4–17. Beijing: Science Press.  Google Scholar
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First citationYan, F.-L., Zhang, L.-B., Zhang, J.-X. & Sun, H.-D. (2007). Chin. Chem. Lett. 18, 1383–1385.  Web of Science CrossRef CAS Google Scholar

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