(3aS,5aR,6R,8aR)-3a-Hydr­oxy-5a-methyl-6-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl]-3a,4,5,5a,6,7,8,8a-octa­hydro-2H-cyclo­penta­[e]benzofuran-2-one

Wang, W.; Tao, H.; Sun, W.; Gu, Q.-Q.; Zhu, W.-M.

doi:10.1107/S1600536807047307

(3aS,5aR,6R,8aR)-3a-Hydroxy-5a-methyl-6-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen-1-yl]-3a,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[e]benzofuran-2-one

W. Wang, H. Tao, W. Sun, Q.-Q. Gu and W.-M. Zhu

The title compound, C₂₁H₃₂O₃, also known as dimethylincisterol A3, was isolated from halotolerant fungus THW-18. It is composed of three fused rings and a side chain. In the crystal structure, the molecules interact with each other via O—H

O hydrogen bonds, resulting in an extended chain along the b axis. The absolute configuration was assigned from the measured optical rotation and reference to the literature.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807047307/av3110sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807047307/av3110Isup2.hkl Contains datablock I

CCDC reference: 667262

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.006 Å
R factor = 0.045
wR factor = 0.113
Data-to-parameter ratio = 8.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.86 Ratio
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.69 Ratio

Alert level C
STRVA01_ALERT_4_C           Flack test results are meaningless.
           From the CIF: _refine_ls_abs_structure_Flack    0.000
           From the CIF: _refine_ls_abs_structure_Flack_su   10.000
PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ...      10.00
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6
PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su ..      10.00

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           25.01
           From the CIF: _reflns_number_total               1965
           Count of symmetry unique reflns         1969
           Completeness (_total/calc)             99.80%
           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 C4     = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C12    = .          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

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

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

Comment top

Dimethylincisterol A3, (I), was first reported as an intermediate to synthesize the (17R)-17-methylincisterol (De Riccardis et al., 1995), and then was isolated from a marine sponge Homaxinella sp. in 2005 (Mansoor et al., 2005). This title compound and related compounds are of interest because of their biological activities (Togashi et al., 1998; Mansoor et al., 2005; Kawagishi et al., 2006). We isolated (I) as a part of our ongoing study characterizing bioactive metabolites from various halotolerant microorganisms. This is our first report about the title compound isolated from halotolerant fungus THW-18 and the results of its X-ray crystallographic study (Fig. 1).

The five-membered N3—C4—C5—C6—C7 ring adopts a twist conformation, and the six-membered N2—C3—C4—N3—C8—C9 ring adopts a half-chair conformation. The corresponding puckering parameters (Cremer & Pople, 1975) are Q = 0.462 (4) Å, φ = 192.5 (5)° and Q = 0.564 (4) Å, θ = 6.1 (4)°, φ = 264 (3)°.

It was not possible to determined the absolute configuration of compound (I) by anomalous dispersion effects, but the positive optical rotation suggested that this compound was dimethylincisterol A3 (Mansoor et al., 2005; Kawagishi et al., 2006).

As shown in Fig. 2, the compounds are linked into a 1-D ribbon along [010] by the O3—H3A···O2ⁱ hydrogen bond. (symmetry code: i = 3 - x, 1/2 + y, 1 - z).

Related literature top

For general background, see: Mansoor et al. (2005); Togashi et al. (1998); Kawagishi et al. (2006); De Riccardis et al. (1995). For related literature, see: Cremer & Pople (1975).

Experimental top

The isolated halotolerant fungal strain THW-18, was isolated from the sediments collected in Hongdao salt field, Qingdao, China. The working strain was cultured under static conditions at 303 K for 45 days in two hundred and fifty 1000-ml conical flasks containing the liquid medium (300 ml/flask) composed of maltose (8 g/L), mannitol (8 g/L), glucose (4 g/L), monosodium glutamate (10 g/L), KH₂PO₄ (0.5 g/L), yeast extract paste (3 g/L), maize paste (1 g/L), and sea salt (100 g/L) after adjusting its pH to 6.5. The fermented whole broth (75 L) was filtered through cheese cloth to separate into supernatant and mycelia. The mycelia were extracted three times with acetone and the acetone solution was concentrated under reduced pressure to afford crude extract (42 g). The crude extract, which was subjected to chromatography over silica gel column using a stepwise gradient elution of petroleum ether-CHCl₃—MeOH, to yield five fractions (Fr.1-Fr.5). Fr.2 was subjected to Sephadex LH-20 eluting with CHCl₃—MeOH (1:1), followed by chromatographing on a silica gel column eluting with CHCl₃—MeOH (30:1) to afford three subfractions (Fr.2–2-1-Fr.2–2-3). The title compound (23 mg) was purified by extensive preparative HPLC using MeOH-H₂O (9:1) from Fr.2–2-2. The single crystals were obtained by slow evaporation of a petroleum ether-acetone (1:1) solution at room temperature on the third day.

Structure description top

As shown in Fig. 2, the compounds are linked into a 1-D ribbon along [010] by the O3—H3A···O2ⁱ hydrogen bond. (symmetry code: i = 3 - x, 1/2 + y, 1 - z).

For general background, see: Mansoor et al. (2005); Togashi et al. (1998); Kawagishi et al. (2006); De Riccardis et al. (1995). For related literature, see: Cremer & Pople (1975).

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of (I), showing 30% probability displacement ellipsoids and the atom-numbering scheme.
	Fig. 2. A view showing the ribbon extending along [010], formed by O—H···O hydrogen bonds (dashed lines). [Symmetry codes: (i) 3 - x, 1/2 + y, 1 - z; (ii) 3 - x, -1/2 + y, 1 - z]

(3aS,5aR,6R,8aR)-3a-Hydroxy-5a-methyl-6-[(1R,2E,4R)-1,4,5-trimethyl-2-hexen- 1-yl]-3a,4,5,5a,6,7,8,8a-octahydro-2H-cyclopenta[e]benzofuran-2-one top

Crystal data top

C₂₁H₃₂O₃	F(000) = 364
M_r = 332.47	D_x = 1.080 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
a = 8.0506 (9) Å	Cell parameters from 2840 reflections
b = 6.7640 (8) Å	θ = 2.3–22.1°
c = 18.858 (2) Å	µ = 0.07 mm⁻¹
β = 95.639 (2)°	T = 298 K
V = 1021.9 (2) Å³	Flake, colourless
Z = 2	0.56 × 0.51 × 0.18 mm

Data collection top

Bruker APEX area-detector diffractometer	1965 independent reflections
Radiation source: fine-focus sealed tube	1247 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
φ and ω scans	θ_max = 25.0°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −9→9
T_min = 0.962, T_max = 0.988	k = −8→8
5311 measured reflections	l = −22→13

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0482P)²] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
1965 reflections	Δρ_max = 0.13 e Å⁻³
224 parameters	Δρ_min = −0.15 e Å⁻³
1 restraint	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0 (10)

Crystal data top

C₂₁H₃₂O₃	V = 1021.9 (2) Å³
M_r = 332.47	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 8.0506 (9) Å	µ = 0.07 mm⁻¹
b = 6.7640 (8) Å	T = 298 K
c = 18.858 (2) Å	0.56 × 0.51 × 0.18 mm
β = 95.639 (2)°

Data collection top

Bruker APEX area-detector diffractometer	1965 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	1247 reflections with I > 2σ(I)
T_min = 0.962, T_max = 0.988	R_int = 0.049
5311 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	H-atom parameters constrained
wR(F²) = 0.113	Δρ_max = 0.13 e Å⁻³
S = 1.05	Δρ_min = −0.15 e Å⁻³
1965 reflections	Absolute structure: Flack, H. D. (1983). Acta Cryst. A39, 876–881.
224 parameters	Absolute structure parameter: 0 (10)
1 restraint

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	1.4534 (3)	0.2461 (4)	0.46674 (13)	0.0650 (8)
O2	1.4101 (3)	0.2856 (5)	0.58115 (15)	0.0768 (9)
O3	1.4982 (3)	0.4173 (5)	0.36379 (13)	0.0699 (8)
H3	1.5217	0.5222	0.3842	0.105*
C1	1.3731 (4)	0.3295 (6)	0.5192 (2)	0.0601 (10)
C2	1.2432 (4)	0.4584 (6)	0.48848 (19)	0.0558 (10)
H2	1.1721	0.5330	0.5138	0.067*
C3	1.2414 (4)	0.4536 (5)	0.41862 (18)	0.0471 (9)
C4	1.3778 (4)	0.3200 (6)	0.39805 (19)	0.0526 (10)
C5	1.3090 (4)	0.1516 (6)	0.3518 (2)	0.0615 (11)
H5A	1.2516	0.0595	0.3804	0.074*
H5B	1.4002	0.0816	0.3330	0.074*
C6	1.1873 (4)	0.2264 (6)	0.28980 (18)	0.0576 (10)
H6A	1.2492	0.3018	0.2574	0.069*
H6B	1.1380	0.1137	0.2638	0.069*
C7	1.0479 (4)	0.3558 (5)	0.31402 (17)	0.0447 (8)
C8	1.1314 (4)	0.5317 (5)	0.35810 (18)	0.0462 (9)
H8	1.2034	0.5999	0.3270	0.055*
C9	0.9890 (4)	0.6699 (6)	0.36851 (19)	0.0589 (10)
H9A	1.0285	0.8045	0.3760	0.071*
H9B	0.9309	0.6295	0.4088	0.071*
C10	0.8755 (4)	0.6518 (6)	0.29844 (19)	0.0601 (10)
H10A	0.8795	0.7724	0.2709	0.072*
H10B	0.7610	0.6289	0.3082	0.072*
C11	0.9407 (4)	0.4739 (5)	0.25643 (17)	0.0515 (9)
H11	1.0169	0.5279	0.2239	0.062*
C12	0.7992 (4)	0.3695 (6)	0.21038 (19)	0.0614 (11)
H12	0.7251	0.3099	0.2427	0.074*
C13	0.6990 (5)	0.5150 (7)	0.16491 (19)	0.0665 (11)
H13	0.7526	0.5764	0.1294	0.080*
C14	0.5453 (5)	0.5652 (7)	0.1695 (2)	0.0693 (12)
H14	0.4914	0.4964	0.2033	0.083*
C15	0.4421 (5)	0.7175 (7)	0.1283 (2)	0.0797 (14)
H15	0.5070	0.7697	0.0912	0.096*
C16	0.2811 (6)	0.6235 (10)	0.0917 (3)	0.1076 (19)
H16	0.2198	0.5626	0.1285	0.129*
C17	0.1679 (7)	0.7832 (14)	0.0527 (3)	0.172 (3)
H17A	0.2280	0.8488	0.0180	0.258*
H17B	0.1358	0.8781	0.0867	0.258*
H17C	0.0699	0.7216	0.0293	0.258*
C18	0.9365 (4)	0.2377 (6)	0.35926 (19)	0.0560 (10)
H18A	0.9008	0.1185	0.3346	0.084*
H18B	0.8406	0.3154	0.3677	0.084*
H18C	0.9977	0.2047	0.4039	0.084*
C19	0.8610 (6)	0.2045 (7)	0.1650 (2)	0.0952 (16)
H19A	0.7688	0.1507	0.1350	0.143*
H19B	0.9110	0.1024	0.1953	0.143*
H19C	0.9424	0.2563	0.1359	0.143*
C20	0.4074 (8)	0.8880 (10)	0.1784 (3)	0.145 (3)
H20A	0.3362	0.8424	0.2130	0.217*
H20B	0.3535	0.9941	0.1512	0.217*
H20C	0.5108	0.9343	0.2024	0.217*
C21	0.3219 (7)	0.4647 (13)	0.0398 (3)	0.155 (3)
H21A	0.3817	0.5221	0.0033	0.233*
H21B	0.2204	0.4061	0.0185	0.233*
H21C	0.3896	0.3649	0.0646	0.233*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0597 (15)	0.0751 (19)	0.0595 (15)	0.0205 (16)	0.0030 (13)	−0.0023 (15)
O2	0.0836 (18)	0.089 (2)	0.0568 (16)	0.0033 (17)	0.0014 (14)	0.0036 (16)
O3	0.0504 (14)	0.095 (2)	0.0679 (17)	−0.0066 (15)	0.0228 (13)	−0.0126 (15)
C1	0.055 (2)	0.064 (3)	0.061 (3)	−0.003 (2)	0.007 (2)	−0.004 (2)
C2	0.053 (2)	0.058 (2)	0.058 (2)	0.004 (2)	0.0127 (18)	−0.009 (2)
C3	0.0423 (18)	0.045 (2)	0.055 (2)	−0.0029 (18)	0.0094 (17)	−0.005 (2)
C4	0.0448 (19)	0.058 (2)	0.056 (2)	0.008 (2)	0.0100 (18)	−0.002 (2)
C5	0.059 (2)	0.058 (2)	0.068 (2)	0.014 (2)	0.007 (2)	−0.019 (2)
C6	0.057 (2)	0.056 (2)	0.060 (2)	0.010 (2)	0.0078 (19)	−0.012 (2)
C7	0.0447 (18)	0.040 (2)	0.0503 (19)	0.0036 (17)	0.0103 (17)	0.0011 (17)
C8	0.0440 (18)	0.044 (2)	0.053 (2)	−0.0012 (18)	0.0121 (17)	0.0024 (18)
C9	0.064 (2)	0.040 (2)	0.072 (3)	0.008 (2)	0.005 (2)	−0.001 (2)
C10	0.067 (2)	0.051 (2)	0.062 (2)	0.008 (2)	0.007 (2)	0.003 (2)
C11	0.055 (2)	0.052 (2)	0.049 (2)	0.001 (2)	0.0124 (17)	0.006 (2)
C12	0.061 (2)	0.068 (3)	0.055 (2)	0.001 (2)	0.002 (2)	0.001 (2)
C13	0.064 (2)	0.087 (3)	0.049 (2)	0.005 (3)	0.007 (2)	0.011 (2)
C14	0.062 (3)	0.092 (3)	0.054 (2)	0.003 (3)	0.005 (2)	0.012 (2)
C15	0.077 (3)	0.104 (4)	0.059 (3)	0.017 (3)	0.011 (2)	0.010 (3)
C16	0.077 (3)	0.162 (6)	0.082 (3)	0.027 (4)	−0.002 (3)	0.020 (4)
C17	0.127 (5)	0.234 (9)	0.146 (5)	0.070 (7)	−0.028 (4)	0.012 (7)
C18	0.058 (2)	0.045 (2)	0.066 (2)	−0.0025 (19)	0.010 (2)	0.005 (2)
C19	0.108 (3)	0.092 (4)	0.080 (3)	0.015 (3)	−0.020 (3)	−0.022 (3)
C20	0.180 (6)	0.135 (6)	0.117 (4)	0.070 (5)	0.005 (4)	−0.031 (4)
C21	0.148 (5)	0.170 (7)	0.136 (5)	0.034 (6)	−0.046 (4)	−0.051 (6)

Geometric parameters (Å, º) top

O1—C1	1.357 (4)	C11—H11	0.9800
O1—C4	1.464 (4)	C12—C13	1.490 (5)
O2—C1	1.213 (4)	C12—C19	1.520 (5)
O3—C4	1.383 (4)	C12—H12	0.9800
O3—H3	0.8200	C13—C14	1.294 (5)
C1—C2	1.439 (5)	C13—H13	0.9300
C2—C3	1.317 (4)	C14—C15	1.493 (6)
C2—H2	0.9300	C14—H14	0.9300
C3—C8	1.472 (4)	C15—C20	1.534 (7)
C3—C4	1.503 (5)	C15—C16	1.544 (7)
C4—C5	1.507 (5)	C15—H15	0.9800
C5—C6	1.536 (5)	C16—C21	1.512 (8)
C5—H5A	0.9700	C16—C17	1.551 (9)
C5—H5B	0.9700	C16—H16	0.9800
C6—C7	1.528 (4)	C17—H17A	0.9600
C6—H6A	0.9700	C17—H17B	0.9600
C6—H6B	0.9700	C17—H17C	0.9600
C7—C18	1.524 (5)	C18—H18A	0.9600
C7—C11	1.542 (5)	C18—H18B	0.9600
C7—C8	1.565 (5)	C18—H18C	0.9600
C8—C9	1.507 (5)	C19—H19A	0.9600
C8—H8	0.9800	C19—H19B	0.9600
C9—C10	1.536 (4)	C19—H19C	0.9600
C9—H9A	0.9700	C20—H20A	0.9600
C9—H9B	0.9700	C20—H20B	0.9600
C10—C11	1.560 (5)	C20—H20C	0.9600
C10—H10A	0.9700	C21—H21A	0.9600
C10—H10B	0.9700	C21—H21B	0.9600
C11—C12	1.535 (5)	C21—H21C	0.9600

C1—O1—C4	108.5 (3)	C7—C11—H11	107.0
C4—O3—H3	109.5	C10—C11—H11	107.0
O2—C1—O1	120.7 (4)	C13—C12—C19	110.5 (3)
O2—C1—C2	129.5 (4)	C13—C12—C11	110.6 (3)
O1—C1—C2	109.7 (3)	C19—C12—C11	113.0 (3)
C3—C2—C1	108.9 (3)	C13—C12—H12	107.5
C3—C2—H2	125.5	C19—C12—H12	107.5
C1—C2—H2	125.5	C11—C12—H12	107.5
C2—C3—C8	135.5 (3)	C14—C13—C12	127.0 (4)
C2—C3—C4	109.7 (3)	C14—C13—H13	116.5
C8—C3—C4	114.5 (3)	C12—C13—H13	116.5
O3—C4—O1	109.0 (3)	C13—C14—C15	129.3 (4)
O3—C4—C3	113.4 (3)	C13—C14—H14	115.4
O1—C4—C3	103.2 (3)	C15—C14—H14	115.4
O3—C4—C5	108.9 (3)	C14—C15—C20	108.9 (3)
O1—C4—C5	110.6 (3)	C14—C15—C16	110.4 (4)
C3—C4—C5	111.6 (3)	C20—C15—C16	112.9 (4)
C4—C5—C6	111.2 (3)	C14—C15—H15	108.2
C4—C5—H5A	109.4	C20—C15—H15	108.2
C6—C5—H5A	109.4	C16—C15—H15	108.2
C4—C5—H5B	109.4	C21—C16—C15	110.8 (4)
C6—C5—H5B	109.4	C21—C16—C17	110.1 (5)
H5A—C5—H5B	108.0	C15—C16—C17	110.7 (6)
C7—C6—C5	113.2 (3)	C21—C16—H16	108.4
C7—C6—H6A	108.9	C15—C16—H16	108.4
C5—C6—H6A	108.9	C17—C16—H16	108.4
C7—C6—H6B	108.9	C16—C17—H17A	109.5
C5—C6—H6B	108.9	C16—C17—H17B	109.5
H6A—C6—H6B	107.8	H17A—C17—H17B	109.5
C18—C7—C6	110.9 (3)	C16—C17—H17C	109.5
C18—C7—C11	110.2 (3)	H17A—C17—H17C	109.5
C6—C7—C11	117.6 (3)	H17B—C17—H17C	109.5
C18—C7—C8	110.3 (3)	C7—C18—H18A	109.5
C6—C7—C8	107.7 (2)	C7—C18—H18B	109.5
C11—C7—C8	99.3 (3)	H18A—C18—H18B	109.5
C3—C8—C9	121.9 (3)	C7—C18—H18C	109.5
C3—C8—C7	109.5 (3)	H18A—C18—H18C	109.5
C9—C8—C7	104.4 (2)	H18B—C18—H18C	109.5
C3—C8—H8	106.7	C12—C19—H19A	109.5
C9—C8—H8	106.7	C12—C19—H19B	109.5
C7—C8—H8	106.7	H19A—C19—H19B	109.5
C8—C9—C10	103.6 (3)	C12—C19—H19C	109.5
C8—C9—H9A	111.0	H19A—C19—H19C	109.5
C10—C9—H9A	111.0	H19B—C19—H19C	109.5
C8—C9—H9B	111.0	C15—C20—H20A	109.5
C10—C9—H9B	111.0	C15—C20—H20B	109.5
H9A—C9—H9B	109.0	H20A—C20—H20B	109.5
C9—C10—C11	107.3 (3)	C15—C20—H20C	109.5
C9—C10—H10A	110.3	H20A—C20—H20C	109.5
C11—C10—H10A	110.3	H20B—C20—H20C	109.5
C9—C10—H10B	110.3	C16—C21—H21A	109.5
C11—C10—H10B	110.3	C16—C21—H21B	109.5
H10A—C10—H10B	108.5	H21A—C21—H21B	109.5
C12—C11—C7	119.6 (3)	C16—C21—H21C	109.5
C12—C11—C10	112.0 (3)	H21A—C21—H21C	109.5
C7—C11—C10	103.6 (3)	H21B—C21—H21C	109.5
C12—C11—H11	107.0

C4—O1—C1—O2	177.5 (3)	C11—C7—C8—C3	179.2 (2)
C4—O1—C1—C2	0.3 (4)	C18—C7—C8—C9	−68.6 (3)
O2—C1—C2—C3	−176.2 (4)	C6—C7—C8—C9	170.2 (3)
O1—C1—C2—C3	0.7 (4)	C11—C7—C8—C9	47.1 (3)
C1—C2—C3—C8	172.0 (4)	C3—C8—C9—C10	−160.2 (3)
C1—C2—C3—C4	−1.4 (4)	C7—C8—C9—C10	−35.8 (4)
C1—O1—C4—O3	119.8 (3)	C8—C9—C10—C11	10.5 (4)
C1—O1—C4—C3	−1.1 (4)	C18—C7—C11—C12	−48.5 (4)
C1—O1—C4—C5	−120.5 (3)	C6—C7—C11—C12	79.9 (4)
C2—C3—C4—O3	−116.3 (4)	C8—C7—C11—C12	−164.4 (3)
C8—C3—C4—O3	68.8 (4)	C18—C7—C11—C10	76.9 (3)
C2—C3—C4—O1	1.5 (4)	C6—C7—C11—C10	−154.6 (3)
C8—C3—C4—O1	−173.4 (3)	C8—C7—C11—C10	−38.9 (3)
C2—C3—C4—C5	120.3 (3)	C9—C10—C11—C12	148.9 (3)
C8—C3—C4—C5	−54.7 (4)	C9—C10—C11—C7	18.7 (4)
O3—C4—C5—C6	−76.4 (4)	C7—C11—C12—C13	172.9 (3)
O1—C4—C5—C6	163.7 (3)	C10—C11—C12—C13	51.6 (4)
C3—C4—C5—C6	49.5 (4)	C7—C11—C12—C19	−62.7 (4)
C4—C5—C6—C7	−53.5 (4)	C10—C11—C12—C19	176.0 (3)
C5—C6—C7—C18	−64.2 (4)	C19—C12—C13—C14	121.2 (5)
C5—C6—C7—C11	167.6 (3)	C11—C12—C13—C14	−112.9 (5)
C5—C6—C7—C8	56.6 (4)	C12—C13—C14—C15	176.2 (4)
C2—C3—C8—C9	7.5 (6)	C13—C14—C15—C20	−111.3 (6)
C4—C3—C8—C9	−179.3 (3)	C13—C14—C15—C16	124.2 (5)
C2—C3—C8—C7	−114.6 (5)	C14—C15—C16—C21	−61.1 (6)
C4—C3—C8—C7	58.7 (4)	C20—C15—C16—C21	176.7 (5)
C18—C7—C8—C3	63.4 (3)	C14—C15—C16—C17	176.5 (4)
C6—C7—C8—C3	−57.8 (3)	C20—C15—C16—C17	54.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3···O2ⁱ	0.82	1.96	2.771 (4)	171

Symmetry code: (i) −x+3, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₂₁H₃₂O₃
M_r	332.47
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	8.0506 (9), 6.7640 (8), 18.858 (2)
β (°)	95.639 (2)
V (Å³)	1021.9 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.56 × 0.51 × 0.18

Data collection
Diffractometer	Bruker APEX area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 2003)
T_min, T_max	0.962, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	5311, 1965, 1247
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.113, 1.05
No. of reflections	1965
No. of parameters	224
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.15
Absolute structure	Flack, H. D. (1983). Acta Cryst. A39, 876–881.
Absolute structure parameter	0 (10)

Computer programs: SMART (Bruker, 2002), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP (Siemens, 1994), WinGX (Farrugia, 1999).

Selected geometric parameters (Å, º) top

O1—C1	1.357 (4)	O3—C4	1.383 (4)
O1—C4	1.464 (4)	O3—H3	0.8200
O2—C1	1.213 (4)	C13—C14	1.294 (5)

C1—O1—C4	108.5 (3)	C18—C7—C8	110.3 (3)
C4—O3—H3	109.5	C6—C7—C8	107.7 (2)
O2—C1—O1	120.7 (4)	C11—C7—C8	99.3 (3)
C2—C3—C8	135.5 (3)	C3—C8—C9	121.9 (3)
C2—C3—C4	109.7 (3)	C3—C8—C7	109.5 (3)
O3—C4—O1	109.0 (3)	C9—C8—C7	104.4 (2)
O1—C4—C3	103.2 (3)	C14—C13—C12	127.0 (4)
O1—C4—C5	110.6 (3)	C14—C13—H13	116.5
C18—C7—C6	110.9 (3)	C12—C13—H13	116.5
C18—C7—C11	110.2 (3)	C13—C14—C15	129.3 (4)
C6—C7—C11	117.6 (3)