3β,5-Dihydr­oxy-15β,16β-methyl­ene-5β-androst-6-en-17-one

Zhou, W.; Zhong, G.-X.; Hu, W.-X.; Xia, C.-N.

doi:10.1107/S1600536807057315

3β,5-Dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one

W. Zhou, G.-X. Zhong, W.-X. Hu and C.-N. Xia

In the title molecule, C₂₀H₂₈O₃, ring A has a regular chair conformation, while ring C has a slightly distorted chair conformation. Ring B shows an asymmetric half-chair conformation and ring D is in an envelope conformation. Rings A and B are cis-fused, while rings B and C and rings C and D are trans-fused. In the crystal structure, intermolecular O—H

O hydrogen bonds link the molecules into a ribbon along the b axis.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057315/is2235sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057315/is2235Isup2.hkl Contains datablock I

CCDC reference: 672935

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.039
wR factor = 0.110
Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.75 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          1
              C20 H28 O3

Alert level G
REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is
            correct. If it is not, please give the correct count in the
            _publ_section_exptl_refinement section of the submitted CIF.
           From the CIF: _diffrn_reflns_theta_max           26.99
           From the CIF: _reflns_number_total               1884
           Count of symmetry unique reflns         1895
           Completeness (_total/calc)             99.42%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16    = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   3 ALERT level C = Check and explain
  11 ALERT level G = General alerts; check

  10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Drospirenone is a new contraceptive drug with the special antimineralocorticoid and antiandrogenic properties (Muhn et al., 1995). In our attempts to synthesize drospirenone, the title compound, (I), was obtained as an intermediate by the alcoholysis of, 3β-acetoxy-5-hydroxy-15β,16β-methylene-5β-androst-6-en-17-one. Here we report the crystal structure of (I).

In the cyclopropyl ring C15/C16/C20, the bond lengths C16—C20 and C15—C20 are different [1.515 (4) versus 1.475 (4) Å], which is also found in 3β-acetoxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one [1.511 (5) and 1.473 (4) Å; Zhou et al., 2007]. The difference in these bond lengths might be caused by a hyperconjugation interaction between the C=O π-bonding and C16—C20 σ-bonding orbitals. However, in the analogous structure of 3β-acetoxy-17,17-ethylenedioxy-15β,16β-methylene-5-androsten-7β-ol these bond lenghts are almost equal [1.499 (6) and 1.493 (6) Å; Zhou et al., 2006].

In the steroid skeleton, ring A has a regular chair conformation, while ring C has a slightly distorted chair conformation. Ring B shows a asymmetric half-chair conformation and ring D is in an envelope conformation. In ring B, atom C9 and atom C10 deviate by 0.390 (4) and -0.435 (4) Å from the mean plane calculated through the ring C5—C8, respectively. In ring D, C13 deviates by 0.486 (3) Å from the mean plane of C14—C17, which makes a dihedral angle of 64.5 (1)° with the cyclopropyl ring C15/C16/C20. In the crystal structure, an intermolecular O—H···O hydrogen bond is found (Table 1), which links the molecules into ribbons along the b axis (Fig. 2). In addition, an intramolecular O—H···O hydrogen bond is found (Table 1).

Related literature top

For related literature, see: Bittler et al. (1984); Muhn et al. (1995); Zhou et al. (2006, 2007).

Experimental top

The title compound was synthesized according to the literature method (Bittler et al., 1984). Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation from a tetrahydrofuran solution.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), with 30% probability displacement ellipsoids.
	Fig. 2. Packing diagram of (I), viewed along the a axis, showing hydrogen bonds as dashed lines. For clarity, H atoms have been omitted except for those involved in hydrogen bonds.

3β,5-Dihydroxy-15β,16β-methylene-5β-androst-6-en-17-one top

Crystal data top

C₂₀H₂₈O₃	F(000) = 344
M_r = 316.42	D_x = 1.249 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2477 reflections
a = 6.5158 (9) Å	θ = 3.3–27.4°
b = 20.592 (3) Å	µ = 0.08 mm⁻¹
c = 6.5877 (9) Å	T = 296 K
β = 107.837 (2)°	Prism, colorless
V = 841.4 (2) Å³	0.30 × 0.20 × 0.20 mm
Z = 2

Data collection top

Bruker APEXII CCD area-detector diffractometer	1884 independent reflections
Radiation source: fine-focus sealed tube	1739 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −7→8
T_min = 0.976, T_max = 0.984	k = −26→26
5279 measured reflections	l = −8→6

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0707P)² + 0.0701P] where P = (F_o² + 2F_c²)/3
1884 reflections	(Δ/σ)_max < 0.001
216 parameters	Δρ_max = 0.19 e Å⁻³
3 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₀H₂₈O₃	V = 841.4 (2) Å³
M_r = 316.42	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 6.5158 (9) Å	µ = 0.08 mm⁻¹
b = 20.592 (3) Å	T = 296 K
c = 6.5877 (9) Å	0.30 × 0.20 × 0.20 mm
β = 107.837 (2)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	1884 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	1739 reflections with I > 2σ(I)
T_min = 0.976, T_max = 0.984	R_int = 0.021
5279 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	3 restraints
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.19 e Å⁻³
1884 reflections	Δρ_min = −0.17 e Å⁻³
216 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	0.0158 (4)	0.57314 (9)	−0.3266 (3)	0.0552 (5)
H1X	−0.091 (4)	0.5628 (18)	−0.416 (4)	0.062 (10)*
O2	0.0413 (3)	0.64237 (9)	0.0343 (3)	0.0509 (5)
H2X	0.030 (10)	0.609 (2)	−0.044 (9)	0.15 (2)*
O3	0.3570 (3)	1.03434 (11)	−0.3503 (3)	0.0623 (5)
C1	−0.1688 (4)	0.70794 (12)	−0.3885 (4)	0.0431 (5)
H1A	−0.2548	0.6747	−0.3486	0.052*
H1B	−0.2674	0.7396	−0.4758	0.052*
C2	−0.0437 (5)	0.67689 (12)	−0.5215 (4)	0.0496 (6)
H2A	0.0307	0.7103	−0.5754	0.060*
H2B	−0.1430	0.6551	−0.6427	0.060*
C3	0.1197 (5)	0.62810 (12)	−0.3921 (4)	0.0494 (6)
H3	0.2077	0.6124	−0.4788	0.059*
C4	0.2652 (4)	0.65956 (11)	−0.1923 (4)	0.0443 (5)
H4A	0.3543	0.6917	−0.2326	0.053*
H4B	0.3602	0.6267	−0.1074	0.053*
C5	0.1422 (4)	0.69255 (10)	−0.0546 (3)	0.0364 (5)
C6	0.3031 (4)	0.72557 (12)	0.1315 (4)	0.0428 (5)
H6	0.3837	0.6995	0.2428	0.051*
C7	0.3376 (4)	0.78913 (12)	0.1477 (4)	0.0427 (5)
H7	0.4451	0.8048	0.2656	0.051*
C8	0.2114 (3)	0.83711 (10)	−0.0151 (3)	0.0342 (4)
H8	0.1020	0.8569	0.0394	0.041*
C9	0.0945 (3)	0.80199 (10)	−0.2272 (3)	0.0331 (4)
H9	0.2088	0.7847	−0.2801	0.040*
C10	−0.0304 (3)	0.74189 (10)	−0.1847 (3)	0.0340 (4)
C11	−0.0357 (4)	0.84930 (12)	−0.4003 (4)	0.0448 (5)
H11A	−0.1603	0.8642	−0.3622	0.054*
H11B	−0.0878	0.8262	−0.5346	0.054*
C12	0.0961 (4)	0.90909 (12)	−0.4311 (4)	0.0462 (6)
H12A	0.2075	0.8954	−0.4915	0.055*
H12B	0.0022	0.9395	−0.5291	0.055*
C13	0.1993 (3)	0.94225 (10)	−0.2162 (4)	0.0369 (5)
C14	0.3449 (3)	0.89105 (10)	−0.0685 (3)	0.0357 (5)
H14	0.4209	0.8700	−0.1581	0.043*
C15	0.5202 (4)	0.92742 (12)	0.0985 (4)	0.0464 (6)
H15	0.6546	0.9043	0.1692	0.056*
C16	0.5362 (4)	0.99388 (12)	0.0006 (4)	0.0463 (6)
H16	0.6788	1.0115	0.0109	0.056*
C17	0.3634 (4)	0.99646 (11)	−0.2073 (4)	0.0427 (5)
C18	0.0169 (4)	0.97291 (13)	−0.1433 (5)	0.0508 (6)
H18A	−0.0374	0.9413	−0.0655	0.076*
H18B	−0.0975	0.9869	−0.2658	0.076*
H18C	0.0723	1.0096	−0.0532	0.076*
C19	−0.1823 (4)	0.76125 (14)	−0.0571 (4)	0.0494 (6)
H19A	−0.2584	0.7236	−0.0329	0.074*
H19B	−0.2837	0.7929	−0.1358	0.074*
H19C	−0.0997	0.7794	0.0774	0.074*
C20	0.4718 (5)	0.98657 (15)	0.2017 (4)	0.0568 (7)
H20A	0.5753	0.9999	0.3353	0.068*
H20B	0.3223	0.9948	0.1916	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0676 (13)	0.0364 (9)	0.0532 (11)	−0.0079 (9)	0.0058 (10)	−0.0006 (8)
O2	0.0630 (12)	0.0439 (10)	0.0448 (10)	−0.0119 (8)	0.0151 (9)	0.0087 (8)
O3	0.0712 (12)	0.0485 (11)	0.0662 (12)	−0.0026 (9)	0.0196 (10)	0.0138 (9)
C1	0.0430 (12)	0.0359 (11)	0.0402 (12)	−0.0042 (9)	−0.0022 (10)	0.0013 (10)
C2	0.0714 (18)	0.0402 (13)	0.0338 (11)	−0.0089 (11)	0.0110 (12)	−0.0015 (10)
C3	0.0641 (16)	0.0358 (12)	0.0516 (14)	−0.0005 (11)	0.0227 (12)	−0.0051 (11)
C4	0.0408 (12)	0.0320 (11)	0.0595 (14)	0.0024 (9)	0.0147 (10)	0.0036 (10)
C5	0.0363 (11)	0.0321 (10)	0.0354 (10)	−0.0007 (9)	0.0029 (9)	0.0057 (8)
C6	0.0425 (12)	0.0418 (12)	0.0352 (11)	−0.0021 (10)	−0.0014 (9)	0.0070 (9)
C7	0.0425 (12)	0.0428 (12)	0.0319 (10)	−0.0033 (9)	−0.0046 (9)	0.0013 (9)
C8	0.0345 (10)	0.0328 (10)	0.0304 (10)	0.0013 (8)	0.0027 (8)	−0.0025 (8)
C9	0.0345 (10)	0.0292 (9)	0.0304 (9)	0.0031 (8)	0.0022 (8)	−0.0003 (8)
C10	0.0305 (9)	0.0345 (10)	0.0330 (10)	0.0004 (8)	0.0036 (8)	−0.0009 (8)
C11	0.0498 (13)	0.0354 (11)	0.0365 (11)	0.0010 (10)	−0.0054 (9)	0.0019 (10)
C12	0.0583 (14)	0.0358 (11)	0.0359 (11)	0.0033 (10)	0.0015 (10)	0.0043 (9)
C13	0.0375 (10)	0.0289 (10)	0.0405 (11)	0.0031 (8)	0.0062 (9)	0.0000 (9)
C14	0.0325 (10)	0.0328 (10)	0.0371 (11)	0.0038 (8)	0.0039 (8)	−0.0012 (9)
C15	0.0387 (11)	0.0411 (13)	0.0497 (13)	−0.0025 (10)	−0.0006 (10)	−0.0007 (10)
C16	0.0411 (12)	0.0372 (12)	0.0586 (14)	−0.0034 (10)	0.0121 (11)	−0.0050 (11)
C17	0.0452 (12)	0.0324 (11)	0.0515 (13)	0.0037 (9)	0.0166 (10)	−0.0030 (10)
C18	0.0396 (11)	0.0418 (13)	0.0692 (17)	0.0079 (10)	0.0142 (12)	−0.0051 (12)
C19	0.0402 (12)	0.0512 (14)	0.0595 (15)	0.0010 (11)	0.0196 (11)	−0.0012 (12)
C20	0.0619 (16)	0.0551 (15)	0.0488 (14)	−0.0132 (13)	0.0101 (12)	−0.0149 (12)

Geometric parameters (Å, º) top

O1—C3	1.451 (3)	C9—H9	0.9800
O1—H1X	0.792 (19)	C10—C19	1.535 (3)
O2—C5	1.442 (3)	C11—C12	1.550 (4)
O2—H2X	0.85 (5)	C11—H11A	0.9700
O3—C17	1.214 (3)	C11—H11B	0.9700
C1—C2	1.509 (4)	C12—C13	1.529 (3)
C1—C10	1.537 (3)	C12—H12A	0.9700
C1—H1A	0.9700	C12—H12B	0.9700
C1—H1B	0.9700	C13—C17	1.534 (3)
C2—C3	1.521 (4)	C13—C18	1.547 (3)
C2—H2A	0.9700	C13—C14	1.547 (3)
C2—H2B	0.9700	C14—C15	1.519 (3)
C3—C4	1.512 (4)	C14—H14	0.9800
C3—H3	0.9800	C15—C20	1.475 (4)
C4—C5	1.540 (3)	C15—C16	1.530 (4)
C4—H4A	0.9700	C15—H15	0.9800
C4—H4B	0.9700	C16—C17	1.483 (4)
C5—C6	1.509 (3)	C16—C20	1.515 (4)
C5—C10	1.562 (3)	C16—H16	0.9800
C6—C7	1.327 (4)	C18—H18A	0.9599
C6—H6	0.9300	C18—H18B	0.9599
C7—C8	1.504 (3)	C18—H18C	0.9599
C7—H7	0.9300	C19—H19A	0.9599
C8—C14	1.517 (3)	C19—H19B	0.9599
C8—C9	1.551 (3)	C19—H19C	0.9599
C8—H8	0.9800	C20—H20A	0.9700
C9—C11	1.541 (3)	C20—H20B	0.9700
C9—C10	1.553 (3)

C3—O1—H1X	112 (3)	C9—C11—H11A	108.9
C5—O2—H2X	107 (4)	C12—C11—H11A	108.9
C2—C1—C10	115.01 (19)	C9—C11—H11B	108.9
C2—C1—H1A	108.5	C12—C11—H11B	108.9
C10—C1—H1A	108.5	H11A—C11—H11B	107.7
C2—C1—H1B	108.5	C13—C12—C11	109.74 (19)
C10—C1—H1B	108.5	C13—C12—H12A	109.7
H1A—C1—H1B	107.5	C11—C12—H12A	109.7
C1—C2—C3	111.4 (2)	C13—C12—H12B	109.7
C1—C2—H2A	109.4	C11—C12—H12B	109.7
C3—C2—H2A	109.4	H12A—C12—H12B	108.2
C1—C2—H2B	109.4	C12—C13—C17	117.64 (19)
C3—C2—H2B	109.4	C12—C13—C18	107.9 (2)
H2A—C2—H2B	108.0	C17—C13—C18	106.49 (18)
O1—C3—C4	107.5 (2)	C12—C13—C14	106.79 (17)
O1—C3—C2	111.8 (2)	C17—C13—C14	100.70 (17)
C4—C3—C2	110.5 (2)	C18—C13—C14	117.7 (2)
O1—C3—H3	109.0	C8—C14—C15	123.38 (18)
C4—C3—H3	109.0	C8—C14—C13	111.09 (17)
C2—C3—H3	109.0	C15—C14—C13	107.45 (18)
C3—C4—C5	113.6 (2)	C8—C14—H14	104.4
C3—C4—H4A	108.8	C15—C14—H14	104.4
C5—C4—H4A	108.8	C13—C14—H14	104.4
C3—C4—H4B	108.8	C20—C15—C14	121.4 (2)
C5—C4—H4B	108.8	C20—C15—C16	60.51 (18)
H4A—C4—H4B	107.7	C14—C15—C16	105.6 (2)
O2—C5—C6	106.38 (17)	C20—C15—H15	117.9
O2—C5—C4	107.91 (19)	C14—C15—H15	117.9
C6—C5—C4	108.69 (19)	C16—C15—H15	117.9
O2—C5—C10	110.33 (17)	C17—C16—C20	118.4 (2)
C6—C5—C10	110.90 (18)	C17—C16—C15	106.9 (2)
C4—C5—C10	112.40 (18)	C20—C16—C15	57.95 (18)
C7—C6—C5	124.6 (2)	C17—C16—H16	119.1
C7—C6—H6	117.7	C20—C16—H16	119.1
C5—C6—H6	117.7	C15—C16—H16	119.1
C6—C7—C8	123.3 (2)	O3—C17—C16	125.1 (2)
C6—C7—H7	118.4	O3—C17—C13	125.4 (2)
C8—C7—H7	118.4	C16—C17—C13	109.4 (2)
C7—C8—C14	114.79 (17)	C13—C18—H18A	109.5
C7—C8—C9	110.28 (17)	C13—C18—H18B	109.5
C14—C8—C9	106.88 (17)	H18A—C18—H18B	109.5
C7—C8—H8	108.2	C13—C18—H18C	109.5
C14—C8—H8	108.2	H18A—C18—H18C	109.5
C9—C8—H8	108.2	H18B—C18—H18C	109.5
C11—C9—C8	112.27 (17)	C10—C19—H19A	109.5
C11—C9—C10	115.91 (17)	C10—C19—H19B	109.5
C8—C9—C10	110.41 (16)	H19A—C19—H19B	109.5
C11—C9—H9	105.8	C10—C19—H19C	109.5
C8—C9—H9	105.8	H19A—C19—H19C	109.5
C10—C9—H9	105.8	H19B—C19—H19C	109.5
C19—C10—C1	106.99 (18)	C15—C20—C16	61.54 (18)
C19—C10—C9	110.70 (19)	C15—C20—H20A	117.6
C1—C10—C9	113.86 (17)	C16—C20—H20A	117.6
C19—C10—C5	110.21 (19)	C15—C20—H20B	117.6
C1—C10—C5	108.32 (17)	C16—C20—H20B	117.6
C9—C10—C5	106.75 (16)	H20A—C20—H20B	114.7
C9—C11—C12	113.41 (19)

C10—C1—C2—C3	56.5 (3)	C8—C9—C11—C12	50.3 (3)
C1—C2—C3—O1	65.3 (3)	C10—C9—C11—C12	178.5 (2)
C1—C2—C3—C4	−54.4 (3)	C9—C11—C12—C13	−52.8 (3)
O1—C3—C4—C5	−68.1 (3)	C11—C12—C13—C17	171.19 (19)
C2—C3—C4—C5	54.2 (3)	C11—C12—C13—C18	−68.4 (2)
C3—C4—C5—O2	68.5 (2)	C11—C12—C13—C14	59.1 (2)
C3—C4—C5—C6	−176.49 (19)	C7—C8—C14—C15	−43.6 (3)
C3—C4—C5—C10	−53.4 (3)	C9—C8—C14—C15	−166.2 (2)
O2—C5—C6—C7	−139.6 (3)	C7—C8—C14—C13	−173.34 (18)
C4—C5—C6—C7	104.5 (3)	C9—C8—C14—C13	64.0 (2)
C10—C5—C6—C7	−19.6 (4)	C12—C13—C14—C8	−67.9 (2)
C5—C6—C7—C8	3.0 (4)	C17—C13—C14—C8	168.77 (17)
C6—C7—C8—C14	−138.5 (3)	C18—C13—C14—C8	53.6 (2)
C6—C7—C8—C9	−17.7 (3)	C12—C13—C14—C15	154.5 (2)
C7—C8—C9—C11	−179.5 (2)	C17—C13—C14—C15	31.1 (2)
C14—C8—C9—C11	−54.1 (2)	C18—C13—C14—C15	−84.1 (2)
C7—C8—C9—C10	49.5 (2)	C8—C14—C15—C20	−89.3 (3)
C14—C8—C9—C10	174.90 (16)	C13—C14—C15—C20	41.9 (3)
C2—C1—C10—C19	−171.9 (2)	C8—C14—C15—C16	−154.0 (2)
C2—C1—C10—C9	65.5 (3)	C13—C14—C15—C16	−22.7 (3)
C2—C1—C10—C5	−53.1 (3)	C20—C15—C16—C17	−113.3 (2)
C11—C9—C10—C19	−75.2 (2)	C14—C15—C16—C17	4.3 (3)
C8—C9—C10—C19	53.9 (2)	C14—C15—C16—C20	117.7 (2)
C11—C9—C10—C1	45.4 (2)	C20—C16—C17—O3	135.8 (3)
C8—C9—C10—C1	174.43 (17)	C15—C16—C17—O3	−161.9 (2)
C11—C9—C10—C5	164.84 (18)	C20—C16—C17—C13	−46.3 (3)
C8—C9—C10—C5	−66.1 (2)	C15—C16—C17—C13	15.9 (3)
O2—C5—C10—C19	46.3 (2)	C12—C13—C17—O3	33.6 (3)
C6—C5—C10—C19	−71.3 (2)	C18—C13—C17—O3	−87.6 (3)
C4—C5—C10—C19	166.8 (2)	C14—C13—C17—O3	149.1 (2)
O2—C5—C10—C1	−70.4 (2)	C12—C13—C17—C16	−144.3 (2)
C6—C5—C10—C1	172.00 (19)	C18—C13—C17—C16	94.6 (2)
C4—C5—C10—C1	50.1 (2)	C14—C13—C17—C16	−28.8 (2)
O2—C5—C10—C9	166.61 (17)	C14—C15—C20—C16	−90.9 (3)
C6—C5—C10—C9	49.0 (2)	C17—C16—C20—C15	93.0 (2)
C4—C5—C10—C9	−72.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2X···O1	0.85 (5)	1.98 (4)	2.734 (3)	148 (6)
O1—H1X···O3ⁱ	0.79 (2)	2.02 (2)	2.811 (3)	178 (4)

Symmetry code: (i) −x, y−1/2, −z−1.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₈O₃
M_r	316.42
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	296
a, b, c (Å)	6.5158 (9), 20.592 (3), 6.5877 (9)
β (°)	107.837 (2)
V (Å³)	841.4 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.976, 0.984
No. of measured, independent and observed [I > 2σ(I)] reflections	5279, 1884, 1739
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.110, 1.06
No. of reflections	1884
No. of parameters	216
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.17

Computer programs: APEX2 (Bruker, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).