(1S*,2S*,5R*,8S*,11S*,14R*,17S*,20R*)-14-Methyl-6-methyl­ene-10,16,18-trioxa­hexa­cyclo­[12.5.1.15,8.01,11.02,8.017,20]henicosane-7,9-dione: natural diter­penoid macrocalyxoformin B

Shi, H.

doi:10.1107/S1600536807060692

organic compounds

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ISSN: 2056-9890

Volume 64| Part 1| January 2008| Page o79

https://doi.org/10.1107/S1600536807060692

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(1S,2S,5R,8S,11S,14R,17S,20R)-14-Methyl-6-methylene-10,16,18-trioxahexacyclo[12.5.1.1^5,8.0^1,11.0^2,8.0^17,20]henicosane-7,9-dione: natural diterpenoid macrocalyxoformin B

Hao Shi ^a ^*

^aThe College of Pharmaceutical Science, Zhejiang University of Technology, Hangzhou 310014, People's Republic of China
^*Correspondence e-mail: shihao@126.com

(Received 11 November 2007; accepted 19 November 2007; online 6 December 2007)

The title compound, C₂₀H₂₄O₅, isolated from Rabdosia var. lophanthoides Hara, is built up from six fused rings. Cyclohexane ring A adopts a chair conformation, ring B exists in a screw-boat conformation and ring C adopts a boat conformation; the three five-membered rings D, E and F adopt envelope conformations.

Related literature

For related literature, see: Wang et al. (1986 ). For ring puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₀H₂₄O₅
M_r = 344.39
Orthorhombic, P 2₁ 2₁ 2₁
a = 7.8450 (10) Å
b = 13.1365 (17) Å
c = 16.178 (2) Å
V = 1667.2 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 (2) K
0.20 × 0.18 × 0.13 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1999 ) T_min = 0.981, T_max = 0.987
7324 measured reflections
1707 independent reflections
1158 reflections with I > 2σ(I)
R_int = 0.151

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.159
S = 0.99
1707 reflections
228 parameters
H-atom parameters constrained
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Puckering parameters (Å, °)

Ring	Q	θ	φ
A	0.478 (5)	24.8 (6)	126.4 (14)
B	0.664 (5)	106.1 (4)	89.3 (4)
C	0.821 (5)	100.1 (3)	54.3 (4)

	Q2	φ2
D	0.473 (5)	324.5 (6)
E	0.365 (5)	321.7 (7)
F	0.330 (5)	140.1 (9)

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536807060692/dn2278sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536807060692/dn2278Isup2.hkl

checkCIF report

Comment top

The diterpenoid macrocalyxoformin B, (I), has been previously isolated from Rabdosia macrocalyx Hara (Wang et al., 1986) and its structure was established from the spectroscopic and chemical evidence. Recently, it was for the first time isolated from Rabdosia var lophanthoides Hara, and its structure was confirmed by an X-ray diffraction study.

The molecule is built up from six fused rings, three six membered and three five membered rings (Fig. 1). Some geometrical features of these rings were investigated using PLATON (Spek, 2003).

Cyclohexane ring A (C1/C11—C14/C20) adopts a chair conformation (Cremer & Pople, 1975), ring B (O10/C9/C8/C2/C1/C11) exists in a screw-boat conformation, ring C (C2—C5/C21/C8) adopts the boat conformation. All the three five-membered rings adopt envelope conformation.

Related literature top

For related literature, see: Wang et al. (1986). For ring puckering parameters, see: Cremer & Pople (1975).

Experimental top

The title compound (I) was isolated from Rabdosia var lophanthoides Hara and crystals suitable for X-ray structure analysis were obtained by slow evaporation from a solution of methanol at room temperature.

Structure description top

The molecule is built up from six fused rings, three six membered and three five membered rings (Fig. 1). Some geometrical features of these rings were investigated using PLATON (Spek, 2003).

For related literature, see: Wang et al. (1986). For ring puckering parameters, see: Cremer & Pople (1975).

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. Molecular view of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.

(1S*,2S*,5R*,8S*,11S*,14R*, 17S*,20R*)-14-Methyl-6-methylene-10,16,18- trioxahexacyclo[12.5.1.1^5,8.0^1,11.0^2,8.0^17,20]henicosane-7,9-dione top

Crystal data top

C₂₀H₂₄O₅	F(000) = 736
M_r = 344.39	D_x = 1.372 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1585 reflections
a = 7.845 (1) Å	θ = 2.5–24.9°
b = 13.1365 (17) Å	µ = 0.10 mm⁻¹
c = 16.178 (2) Å	T = 298 K
V = 1667.2 (4) Å³	Plate, colorless
Z = 4	0.20 × 0.18 × 0.13 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1707 independent reflections
Radiation source: fine-focus sealed tube	1158 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.151
φ and ω scans	θ_max = 25.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1999)	h = −8→9
T_min = 0.981, T_max = 0.987	k = −9→15
7324 measured reflections	l = −19→18

Refinement top

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.159	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0846P)²] where P = (F_o² + 2F_c²)/3
1707 reflections	(Δ/σ)_max = 0.001
228 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₀H₂₄O₅	V = 1667.2 (4) Å³
M_r = 344.39	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 7.845 (1) Å	µ = 0.10 mm⁻¹
b = 13.1365 (17) Å	T = 298 K
c = 16.178 (2) Å	0.20 × 0.18 × 0.13 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1707 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1999)	1158 reflections with I > 2σ(I)
T_min = 0.981, T_max = 0.987	R_int = 0.151
7324 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.159	H-atom parameters constrained
S = 0.99	Δρ_max = 0.27 e Å⁻³
1707 reflections	Δρ_min = −0.23 e Å⁻³
228 parameters

Special details top

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

	x	y	z	U_iso*/U_eq
O1	0.2722 (6)	0.1295 (3)	0.8777 (3)	0.0774 (13)
O2	0.1286 (5)	0.3379 (3)	0.8514 (2)	0.0648 (11)
O10	0.5239 (5)	0.1278 (3)	0.8173 (2)	0.0528 (10)
O16	0.6881 (4)	0.3328 (3)	0.54354 (19)	0.0531 (10)
O18	0.4526 (4)	0.3456 (3)	0.6322 (2)	0.0485 (9)
C1	0.6034 (6)	0.2829 (4)	0.7468 (3)	0.0374 (11)
C2	0.5314 (6)	0.3540 (4)	0.8156 (3)	0.0403 (12)
H2	0.4508	0.4005	0.7890	0.048*
C3	0.6638 (7)	0.4202 (4)	0.8615 (3)	0.0517 (14)
H3A	0.7590	0.3776	0.8779	0.062*
H3B	0.7069	0.4715	0.8238	0.062*
C4	0.5914 (7)	0.4733 (4)	0.9387 (3)	0.0528 (14)
H4A	0.5317	0.5345	0.9217	0.063*
H4B	0.6853	0.4937	0.9740	0.063*
C5	0.4682 (7)	0.4057 (4)	0.9889 (3)	0.0490 (14)
H5	0.4809	0.4174	1.0485	0.059*
C6	0.2874 (7)	0.4183 (4)	0.9622 (3)	0.0475 (13)
C7	0.2569 (7)	0.3448 (4)	0.8912 (3)	0.0443 (12)
C8	0.4269 (6)	0.2882 (4)	0.8792 (3)	0.0421 (12)
C9	0.3966 (7)	0.1760 (4)	0.8572 (3)	0.0510 (14)
C11	0.6700 (7)	0.1866 (4)	0.7881 (3)	0.0427 (12)
H11	0.7402	0.2059	0.8357	0.051*
C12	0.7723 (7)	0.1176 (4)	0.7328 (3)	0.0523 (14)
H12A	0.7007	0.0926	0.6883	0.063*
H12B	0.8129	0.0596	0.7642	0.063*
C13	0.9228 (7)	0.1754 (5)	0.6971 (3)	0.0547 (15)
H13A	0.9869	0.1302	0.6613	0.066*
H13B	0.9972	0.1962	0.7418	0.066*
C14	0.8695 (6)	0.2705 (4)	0.6473 (3)	0.0439 (13)
C15	0.7866 (7)	0.2448 (4)	0.5647 (3)	0.0542 (15)
H15A	0.8725	0.2315	0.5230	0.065*
H15B	0.7140	0.1853	0.5699	0.065*
C17	0.6237 (7)	0.3750 (4)	0.6172 (3)	0.0442 (12)
H17	0.6306	0.4494	0.6142	0.053*
C19	0.4542 (7)	0.2586 (4)	0.6866 (3)	0.0437 (12)
H19A	0.4755	0.1963	0.6562	0.052*
H19B	0.3471	0.2523	0.7162	0.052*
C20	0.7337 (6)	0.3367 (4)	0.6893 (3)	0.0400 (11)
H20	0.7872	0.3941	0.7180	0.048*
C21	0.5012 (7)	0.2938 (4)	0.9666 (3)	0.0483 (13)
H21A	0.6221	0.2782	0.9668	0.058*
H21B	0.4425	0.2480	1.0041	0.058*
C22	0.1647 (7)	0.4771 (5)	0.9914 (4)	0.0605 (16)
H22A	0.1859	0.5197	1.0361	0.073*
H22B	0.0572	0.4758	0.9672	0.073*
C23	1.0269 (7)	0.3360 (5)	0.6295 (3)	0.0599 (15)
H23A	1.1118	0.2954	0.6023	0.090*
H23B	1.0722	0.3616	0.6806	0.090*
H23C	0.9955	0.3920	0.5945	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.091 (3)	0.042 (2)	0.099 (3)	−0.013 (2)	0.041 (3)	−0.008 (2)
O2	0.057 (2)	0.072 (3)	0.065 (2)	0.008 (2)	−0.006 (2)	−0.013 (2)
O10	0.071 (2)	0.0318 (19)	0.0556 (19)	0.0020 (19)	0.017 (2)	0.0054 (17)
O16	0.067 (2)	0.058 (2)	0.0344 (17)	0.002 (2)	0.0020 (17)	0.0028 (17)
O18	0.049 (2)	0.051 (2)	0.0454 (18)	0.0031 (19)	−0.0048 (17)	0.0100 (17)
C1	0.047 (3)	0.031 (3)	0.034 (2)	0.001 (2)	0.001 (2)	−0.001 (2)
C2	0.049 (3)	0.034 (3)	0.038 (2)	0.002 (2)	0.001 (2)	−0.001 (2)
C3	0.061 (3)	0.047 (3)	0.048 (3)	−0.009 (3)	0.004 (3)	−0.009 (3)
C4	0.064 (3)	0.047 (3)	0.047 (3)	0.000 (3)	−0.003 (3)	−0.011 (3)
C5	0.063 (3)	0.048 (3)	0.036 (2)	0.004 (3)	−0.001 (3)	−0.004 (2)
C6	0.064 (3)	0.039 (3)	0.039 (3)	0.002 (3)	0.008 (3)	0.001 (2)
C7	0.047 (3)	0.046 (3)	0.040 (2)	0.001 (3)	0.001 (2)	0.007 (2)
C8	0.054 (3)	0.033 (3)	0.039 (3)	0.003 (2)	0.006 (2)	−0.001 (2)
C9	0.067 (4)	0.039 (3)	0.047 (3)	0.002 (3)	0.014 (3)	0.006 (3)
C11	0.052 (3)	0.036 (3)	0.040 (2)	0.005 (3)	0.000 (2)	0.002 (2)
C12	0.063 (3)	0.039 (3)	0.055 (3)	0.014 (3)	0.008 (3)	0.001 (2)
C13	0.058 (3)	0.054 (4)	0.052 (3)	0.014 (3)	−0.001 (3)	−0.008 (3)
C14	0.045 (3)	0.047 (3)	0.040 (2)	0.001 (3)	0.004 (2)	−0.003 (2)
C15	0.065 (4)	0.054 (4)	0.044 (3)	0.008 (3)	0.006 (3)	−0.005 (3)
C17	0.050 (3)	0.044 (3)	0.039 (3)	−0.004 (3)	−0.002 (2)	−0.002 (2)
C19	0.059 (3)	0.033 (3)	0.039 (2)	−0.003 (3)	0.005 (3)	0.002 (2)
C20	0.049 (3)	0.036 (3)	0.035 (2)	−0.003 (2)	0.002 (2)	0.002 (2)
C21	0.063 (3)	0.045 (3)	0.037 (2)	0.007 (3)	0.000 (3)	0.007 (2)
C22	0.066 (4)	0.050 (4)	0.065 (4)	0.002 (3)	0.010 (3)	−0.009 (3)
C23	0.049 (3)	0.075 (4)	0.056 (3)	−0.001 (3)	0.006 (3)	−0.005 (3)

Geometric parameters (Å, º) top

O1—C9	1.199 (7)	C8—C21	1.531 (7)
O2—C7	1.199 (6)	C8—C9	1.534 (7)
O10—C9	1.348 (6)	C11—C12	1.505 (7)
O10—C11	1.461 (6)	C11—H11	0.9800
O16—C17	1.408 (6)	C12—C13	1.518 (7)
O16—C15	1.432 (6)	C12—H12A	0.9700
O18—C17	1.418 (6)	C12—H12B	0.9700
O18—C19	1.443 (6)	C13—C14	1.544 (7)
C1—C11	1.523 (7)	C13—H13A	0.9700
C1—C20	1.552 (6)	C13—H13B	0.9700
C1—C19	1.555 (7)	C14—C15	1.523 (7)
C1—C2	1.558 (6)	C14—C23	1.533 (8)
C2—C3	1.545 (7)	C14—C20	1.534 (7)
C2—C8	1.575 (7)	C15—H15A	0.9700
C2—H2	0.9800	C15—H15B	0.9700
C3—C4	1.539 (7)	C17—C20	1.536 (7)
C3—H3A	0.9700	C17—H17	0.9800
C3—H3B	0.9700	C19—H19A	0.9700
C4—C5	1.544 (8)	C19—H19B	0.9700
C4—H4A	0.9700	C20—H20	0.9800
C4—H4B	0.9700	C21—H21A	0.9700
C5—C6	1.492 (8)	C21—H21B	0.9700
C5—C21	1.536 (7)	C22—H22A	0.9300
C5—H5	0.9800	C22—H22B	0.9300
C6—C22	1.321 (7)	C23—H23A	0.9600
C6—C7	1.520 (7)	C23—H23B	0.9600
C7—C8	1.539 (7)	C23—H23C	0.9600

C9—O10—C11	119.2 (4)	C13—C12—H12A	109.7
C17—O16—C15	108.0 (4)	C11—C12—H12B	109.7
C17—O18—C19	108.2 (4)	C13—C12—H12B	109.7
C11—C1—C20	114.5 (4)	H12A—C12—H12B	108.2
C11—C1—C19	111.3 (4)	C12—C13—C14	113.1 (4)
C20—C1—C19	102.4 (4)	C12—C13—H13A	109.0
C11—C1—C2	108.0 (4)	C14—C13—H13A	109.0
C20—C1—C2	113.2 (4)	C12—C13—H13B	109.0
C19—C1—C2	107.3 (4)	C14—C13—H13B	109.0
C3—C2—C1	115.9 (4)	H13A—C13—H13B	107.8
C3—C2—C8	110.2 (4)	C15—C14—C23	107.7 (4)
C1—C2—C8	109.1 (4)	C15—C14—C20	102.6 (4)
C3—C2—H2	107.1	C23—C14—C20	109.0 (4)
C1—C2—H2	107.1	C15—C14—C13	113.2 (5)
C8—C2—H2	107.1	C23—C14—C13	109.5 (4)
C4—C3—C2	113.4 (4)	C20—C14—C13	114.5 (4)
C4—C3—H3A	108.9	O16—C15—C14	105.1 (4)
C2—C3—H3A	108.9	O16—C15—H15A	110.7
C4—C3—H3B	108.9	C14—C15—H15A	110.7
C2—C3—H3B	108.9	O16—C15—H15B	110.7
H3A—C3—H3B	107.7	C14—C15—H15B	110.7
C3—C4—C5	113.5 (4)	H15A—C15—H15B	108.8
C3—C4—H4A	108.9	O16—C17—O18	112.2 (4)
C5—C4—H4A	108.9	O16—C17—C20	108.2 (4)
C3—C4—H4B	108.9	O18—C17—C20	108.2 (4)
C5—C4—H4B	108.9	O16—C17—H17	109.4
H4A—C4—H4B	107.7	O18—C17—H17	109.4
C6—C5—C21	101.4 (5)	C20—C17—H17	109.4
C6—C5—C4	112.3 (4)	O18—C19—C1	103.1 (4)
C21—C5—C4	108.7 (4)	O18—C19—H19A	111.2
C6—C5—H5	111.3	C1—C19—H19A	111.2
C21—C5—H5	111.3	O18—C19—H19B	111.2
C4—C5—H5	111.3	C1—C19—H19B	111.2
C22—C6—C5	130.8 (5)	H19A—C19—H19B	109.1
C22—C6—C7	121.8 (5)	C14—C20—C17	103.8 (4)
C5—C6—C7	107.3 (4)	C14—C20—C1	117.7 (4)
O2—C7—C6	125.9 (5)	C17—C20—C1	103.5 (4)
O2—C7—C8	128.5 (5)	C14—C20—H20	110.4
C6—C7—C8	105.4 (4)	C17—C20—H20	110.4
C21—C8—C9	108.7 (4)	C1—C20—H20	110.4
C21—C8—C7	101.0 (4)	C8—C21—C5	101.5 (4)
C9—C8—C7	111.1 (4)	C8—C21—H21A	111.5
C21—C8—C2	112.2 (4)	C5—C21—H21A	111.5
C9—C8—C2	117.1 (4)	C8—C21—H21B	111.5
C7—C8—C2	105.6 (4)	C5—C21—H21B	111.5
O1—C9—O10	119.7 (5)	H21A—C21—H21B	109.3
O1—C9—C8	123.5 (5)	C6—C22—H22A	120.0
O10—C9—C8	116.6 (5)	C6—C22—H22B	120.0
O10—C11—C12	107.0 (4)	H22A—C22—H22B	120.0
O10—C11—C1	108.2 (4)	C14—C23—H23A	109.5
C12—C11—C1	115.0 (4)	C14—C23—H23B	109.5
O10—C11—H11	108.9	H23A—C23—H23B	109.5
C12—C11—H11	108.9	C14—C23—H23C	109.5
C1—C11—H11	108.9	H23A—C23—H23C	109.5
C11—C12—C13	109.9 (4)	H23B—C23—H23C	109.5
C11—C12—H12A	109.7

C11—C1—C2—C3	82.7 (5)	C2—C1—C11—O10	71.0 (5)
C20—C1—C2—C3	−45.1 (5)	C20—C1—C11—C12	−42.5 (6)
C19—C1—C2—C3	−157.3 (4)	C19—C1—C11—C12	73.0 (5)
C11—C1—C2—C8	−42.3 (5)	C2—C1—C11—C12	−169.5 (4)
C20—C1—C2—C8	−170.1 (4)	O10—C11—C12—C13	177.5 (4)
C19—C1—C2—C8	77.7 (4)	C1—C11—C12—C13	57.4 (6)
C1—C2—C3—C4	−169.3 (4)	C11—C12—C13—C14	−58.3 (6)
C8—C2—C3—C4	−44.8 (6)	C12—C13—C14—C15	−71.9 (6)
C2—C3—C4—C5	39.5 (6)	C12—C13—C14—C23	168.0 (5)
C3—C4—C5—C6	−91.0 (6)	C12—C13—C14—C20	45.3 (6)
C3—C4—C5—C21	20.4 (6)	C17—O16—C15—C14	−34.5 (5)
C21—C5—C6—C22	149.2 (6)	C23—C14—C15—O16	−81.1 (5)
C4—C5—C6—C22	−95.0 (6)	C20—C14—C15—O16	33.8 (5)
C21—C5—C6—C7	−28.9 (5)	C13—C14—C15—O16	157.7 (4)
C4—C5—C6—C7	86.9 (5)	C15—O16—C17—O18	−98.7 (5)
C22—C6—C7—O2	6.0 (8)	C15—O16—C17—C20	20.6 (5)
C5—C6—C7—O2	−175.7 (5)	C19—O18—C17—O16	95.5 (5)
C22—C6—C7—C8	−177.4 (5)	C19—O18—C17—C20	−23.9 (5)
C5—C6—C7—C8	0.9 (5)	C17—O18—C19—C1	37.8 (5)
O2—C7—C8—C21	−156.0 (6)	C11—C1—C19—O18	−158.8 (4)
C6—C7—C8—C21	27.5 (5)	C20—C1—C19—O18	−36.1 (5)
O2—C7—C8—C9	−40.9 (7)	C2—C1—C19—O18	83.3 (4)
C6—C7—C8—C9	142.6 (4)	C15—C14—C20—C17	−20.9 (5)
O2—C7—C8—C2	87.0 (6)	C23—C14—C20—C17	93.1 (5)
C6—C7—C8—C2	−89.5 (4)	C13—C14—C20—C17	−143.9 (5)
C3—C2—C8—C21	−9.1 (6)	C15—C14—C20—C1	92.7 (5)
C1—C2—C8—C21	119.2 (4)	C23—C14—C20—C1	−153.3 (4)
C3—C2—C8—C9	−135.8 (5)	C13—C14—C20—C1	−30.3 (6)
C1—C2—C8—C9	−7.5 (6)	O16—C17—C20—C14	1.4 (5)
C3—C2—C8—C7	100.0 (5)	O18—C17—C20—C14	123.2 (4)
C1—C2—C8—C7	−131.7 (4)	O16—C17—C20—C1	−122.1 (4)
C11—O10—C9—O1	176.3 (5)	O18—C17—C20—C1	−0.3 (5)
C11—O10—C9—C8	−8.0 (6)	C11—C1—C20—C14	28.6 (5)
C21—C8—C9—O1	82.9 (7)	C19—C1—C20—C14	−91.9 (4)
C7—C8—C9—O1	−27.3 (7)	C2—C1—C20—C14	152.9 (4)
C2—C8—C9—O1	−148.7 (5)	C11—C1—C20—C17	142.4 (4)
C21—C8—C9—O10	−92.6 (5)	C19—C1—C20—C17	21.8 (5)
C7—C8—C9—O10	157.1 (4)	C2—C1—C20—C17	−93.3 (4)
C2—C8—C9—O10	35.8 (6)	C9—C8—C21—C5	−162.2 (4)
C9—O10—C11—C12	−169.4 (4)	C7—C8—C21—C5	−45.3 (5)
C9—O10—C11—C1	−45.0 (5)	C2—C8—C21—C5	66.7 (5)
C20—C1—C11—O10	−162.0 (4)	C6—C5—C21—C8	46.3 (5)
C19—C1—C11—O10	−46.5 (5)	C4—C5—C21—C8	−72.2 (5)

Experimental details

Crystal data
Chemical formula	C₂₀H₂₄O₅
M_r	344.39
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	298
a, b, c (Å)	7.845 (1), 13.1365 (17), 16.178 (2)
V (Å³)	1667.2 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.20 × 0.18 × 0.13

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1999)
T_min, T_max	0.981, 0.987
No. of measured, independent and observed [I > 2σ(I)] reflections	7324, 1707, 1158
R_int	0.151
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.159, 0.99
No. of reflections	1707
No. of parameters	228
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.23

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Puckering parameters top

Ring	Q, Å	θ,°	φ,°
A	0.478 (5)	24.8 (6)	126.4 (14)
B	0.664 (5)	106.1 (4)	89.3 (4)
C	0.821 (5)	100.1 (3)	54.3 (4)

	Q2, Å	φ2, °
D	0.473 (5)	324.5 (6)
E	0.365 (5)	321.7 (7)
F	0.330 (5)	140.1 (9)

Acknowledgements

This project was supported by the Natural Science Foundation of Zhejiang Province, China (grant No. Y205318).

References

Bruker (1999). SMART (Version 5.611), SAINT (Version 6.02a) and SADABS (Version 2.08). Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany. Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Z. Q., Wang, X. R., Dong, J. G. & Xue, Z. W. (1986). Acta Bot. Sin. 28, 79–85. CAS Google Scholar

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