2a,3a-Dihydroxy­androstan-16-one

Zhang, L.; Fang, X.; Hao, X.-J.; Lu, Y.

doi:10.1107/S1600536809029493

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 8| August 2009| Page o2043

doi:10.1107/S1600536809029493

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2a,3a-Dihydroxyandrostan-16-one

Li Zhang,^a Xin Fang,^b Xiao-Jiang Hao ^b and Yang Lu ^a ^*

^aInstitute of Materia Medica, Chinese Academy of Medical Sciences, and Peking Union Medical College, 1 Xiannong Tan Street, Beijing 100050, People's Republic of China, and ^bState Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, Yunnan, People's Republic of China
^*Correspondence e-mail: luy@imm.ac.cn

(Received 24 June 2009; accepted 24 July 2009; online 31 July 2009)

The title compound, C₁₉H₂₈O₄, is a new androstane steroid derivative. In the crystal, molecules are linked along the a axis by intermolecular O—H⋯O hydrogen bonds.

Related literature

The title compound was obtained from the methanol extract of stems of Trichilia claussenii by column chromatograph, see: Pupo et al. (1997 ). It shows strong insecticidal activity, see: Champagne et al. (1992 ).

Experimental

Crystal data

C₁₉H₂₈O₄
M_r = 320.41
Monoclinic, P 2₁
a = 10.8687 (2) Å
b = 6.3379 (1) Å
c = 12.9038 (2) Å
β = 112.882 (1)°
V = 818.93 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.20 × 0.20 × 0.20 mm

Data collection

MAC DIP 2030K diffractometer
Absorption correction: none
2065 measured reflections
2065 independent reflections
1929 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.105
S = 1.14
2065 reflections
208 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O1ⁱ	0.82	2.03	2.8088 (19)	158
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+1]$ .

Data collection: DENZO (Otwinowski & Minor, 1997 ); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809029493/jh2087sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809029493/jh2087Isup2.hkl

checkCIF report

Comment top

The title compound,(I), was yielded from the methanol extract of stems of Trichilia claussenii by column chromatographies (Pupo et al., 1997) and recrystasllized from methanol-hexane(1:1). As it shows strong biological activities against insects (Champagne et al., 1992) we have determined its crystal stucture, Fig. 1, Table 1.

In this structure, rings A,B and C adopt chair conformations, and both ring D,E adopt envelope conformations. The dihedral angle between the least-squares plane through the 6 atoms of rings A and B is 9.2 (1)°, and that between rings B and C and that between rings C and D are 175.0 (2)° and 2.5 (1)°, respectively.

Besides, the molecules of the title compound are linked into each other along a axis, by intermolecular hydrogen bonds O—H···O. Atom O2 acts as hydrogen-bond donor to atom O1 at (-x, y + 1/2, -z + 1). Molecules pack in ribbons along the b axis, Fig. 2.

Related literature top

The title compound was obtained from the methanol extract of stems of Trichilia claussenii by column chromatograph, see: Pupo et al. (1997). It shows strong insecticidal activity, see: Champagne et al. (1992);

Experimental top

The title compound was prepared according to the procedure of extracting Trichilia claussenii (Pupo et al., 1997). At the temprature of 283 K and unventilated condition, single crystals of (I) were obtained from mixed solvent of methanol-hexane(1:1) within two weeks.

Computing details top

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. View of the molecule showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. The molecular packing of (I) viewed down the b axis.

2a,3a-Dihydroxyandrostan-16-one top

Crystal data top

C₁₉H₂₈O₄	F(000) = 348
M_r = 320.41	D_x = 1.299 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 2065 reflections
a = 10.8687 (2) Å	θ = 1.7–27.6°
b = 6.3379 (1) Å	µ = 0.09 mm⁻¹
c = 12.9038 (2) Å	T = 295 K
β = 112.882 (1)°	Block, colourless
V = 818.93 (2) Å³	0.20 × 0.20 × 0.20 mm
Z = 2

Data collection top

MAC DIP 2030K diffractometer	1929 reflections with I > 2σ(I)
Radiation source: rotate anode	R_int = 0.015
Graphite monochromator	θ_max = 27.6°, θ_min = 1.7°
Detector resolution: 0 pixels mm^-1	h = −14→13
ω scans	k = 0→8
2065 measured reflections	l = 0→16
2065 independent reflections

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.14	w = 1/[σ²(F_o²) + (0.0593P)² + 0.0933P] where P = (F_o² + 2F_c²)/3
2065 reflections	(Δ/σ)_max < 0.001
208 parameters	Δρ_max = 0.26 e Å⁻³
1 restraint	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₉H₂₈O₄	V = 818.93 (2) Å³
M_r = 320.41	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.8687 (2) Å	µ = 0.09 mm⁻¹
b = 6.3379 (1) Å	T = 295 K
c = 12.9038 (2) Å	0.20 × 0.20 × 0.20 mm
β = 112.882 (1)°

Data collection top

MAC DIP 2030K diffractometer	1929 reflections with I > 2σ(I)
2065 measured reflections	R_int = 0.015
2065 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	1 restraint
wR(F²) = 0.105	H-atom parameters constrained
S = 1.14	Δρ_max = 0.26 e Å⁻³
2065 reflections	Δρ_min = −0.15 e Å⁻³
208 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	0.10604 (14)	0.6665 (3)	0.44798 (11)	0.0387 (3)
O2	0.09261 (16)	1.0230 (3)	0.48050 (15)	0.0530 (5)
H2A	0.0221	1.0426	0.4882	0.080*
O3	−0.09685 (18)	1.0625 (3)	0.25157 (18)	0.0597 (5)
H3A	−0.1755	1.0667	0.2083	0.089*
O4	0.61221 (19)	0.0525 (4)	0.09632 (16)	0.0657 (5)
C1	0.17314 (18)	0.9035 (3)	0.34250 (16)	0.0321 (4)
H1A	0.2610	0.9394	0.3976	0.038*
H1B	0.1443	1.0113	0.2846	0.038*
C2	0.07349 (19)	0.8750 (3)	0.39679 (18)	0.0371 (4)
C3	−0.0693 (2)	0.8638 (4)	0.3084 (2)	0.0423 (5)
H3B	−0.1314	0.8411	0.3457	0.051*
C4	−0.08066 (18)	0.6822 (4)	0.22815 (18)	0.0419 (5)
H4B	−0.1622	0.6999	0.1618	0.050*
H4C	−0.0886	0.5516	0.2642	0.050*
C5	0.03684 (17)	0.6613 (4)	0.19065 (15)	0.0337 (4)
H5A	0.0300	0.7763	0.1379	0.040*
C6	0.02645 (19)	0.4533 (4)	0.12841 (17)	0.0418 (5)
H6A	0.0208	0.3383	0.1760	0.050*
H6B	−0.0550	0.4533	0.0611	0.050*
C7	0.14492 (19)	0.4159 (4)	0.09552 (16)	0.0425 (5)
H7A	0.1436	0.5195	0.0398	0.051*
H7B	0.1371	0.2771	0.0618	0.051*
C8	0.27756 (17)	0.4311 (3)	0.19700 (14)	0.0294 (4)
H8A	0.2807	0.3202	0.2509	0.035*
C9	0.28860 (17)	0.6477 (3)	0.25428 (14)	0.0278 (4)
H9	0.2777	0.7530	0.1958	0.033*
C10	0.17217 (16)	0.6848 (3)	0.29237 (14)	0.0273 (4)
C11	0.42783 (17)	0.6878 (4)	0.34704 (16)	0.0357 (4)
H11A	0.4325	0.8331	0.3720	0.043*
H11B	0.4390	0.5978	0.4109	0.043*
C12	0.54289 (19)	0.6468 (3)	0.30905 (19)	0.0383 (5)
H12A	0.5399	0.7492	0.2523	0.046*
H12B	0.6275	0.6625	0.3725	0.046*
C13	0.53218 (18)	0.4254 (3)	0.26115 (15)	0.0314 (4)
C14	0.39575 (18)	0.4035 (3)	0.16258 (15)	0.0311 (4)
H14	0.3903	0.5191	0.1105	0.037*
C15	0.4097 (2)	0.2001 (4)	0.10396 (17)	0.0429 (5)
H15A	0.3818	0.0783	0.1349	0.051*
H15B	0.3572	0.2069	0.0237	0.051*
C16	0.5576 (2)	0.1902 (5)	0.12818 (18)	0.0455 (5)
C17	0.6267 (2)	0.3747 (4)	0.2021 (2)	0.0451 (5)
H17A	0.6348	0.4934	0.1577	0.054*
H17B	0.7147	0.3357	0.2558	0.054*
C18	0.5558 (2)	0.2595 (4)	0.35272 (18)	0.0428 (5)
H18A	0.4971	0.2857	0.3910	0.064*
H18B	0.6468	0.2667	0.4056	0.064*
H18C	0.5382	0.1217	0.3192	0.064*
C19	0.17183 (18)	0.5448 (3)	0.39026 (15)	0.0314 (4)
H19A	0.1239	0.4144	0.3617	0.038*
H19B	0.2624	0.5108	0.4406	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0390 (7)	0.0436 (8)	0.0434 (7)	0.0018 (7)	0.0270 (6)	0.0048 (7)
O2	0.0462 (9)	0.0557 (11)	0.0714 (10)	−0.0022 (8)	0.0384 (8)	−0.0216 (9)
O3	0.0445 (9)	0.0469 (10)	0.0889 (13)	0.0149 (8)	0.0274 (9)	0.0156 (10)
O4	0.0664 (11)	0.0689 (13)	0.0684 (11)	0.0217 (10)	0.0334 (9)	−0.0171 (10)
C1	0.0285 (8)	0.0285 (10)	0.0453 (10)	−0.0002 (7)	0.0209 (8)	0.0004 (8)
C2	0.0349 (10)	0.0361 (11)	0.0491 (11)	0.0015 (8)	0.0260 (9)	−0.0001 (9)
C3	0.0313 (10)	0.0423 (12)	0.0615 (13)	0.0066 (9)	0.0271 (10)	0.0073 (11)
C4	0.0241 (9)	0.0481 (12)	0.0516 (11)	−0.0003 (9)	0.0128 (8)	0.0063 (11)
C5	0.0270 (8)	0.0364 (10)	0.0349 (8)	0.0024 (8)	0.0088 (7)	0.0054 (9)
C6	0.0275 (9)	0.0485 (13)	0.0389 (10)	−0.0027 (9)	0.0015 (8)	−0.0040 (9)
C7	0.0374 (10)	0.0499 (13)	0.0332 (9)	0.0025 (10)	0.0062 (8)	−0.0093 (10)
C8	0.0299 (8)	0.0310 (9)	0.0274 (8)	−0.0005 (7)	0.0113 (7)	−0.0021 (7)
C9	0.0274 (8)	0.0281 (9)	0.0321 (8)	0.0000 (7)	0.0160 (7)	0.0019 (7)
C10	0.0249 (8)	0.0268 (8)	0.0326 (8)	0.0000 (7)	0.0138 (6)	0.0033 (7)
C11	0.0277 (8)	0.0367 (10)	0.0460 (10)	−0.0052 (8)	0.0177 (8)	−0.0122 (9)
C12	0.0307 (9)	0.0337 (11)	0.0563 (12)	−0.0050 (8)	0.0235 (9)	−0.0087 (9)
C13	0.0309 (9)	0.0295 (9)	0.0386 (9)	−0.0002 (8)	0.0187 (8)	−0.0001 (8)
C14	0.0377 (9)	0.0296 (10)	0.0289 (8)	0.0043 (8)	0.0162 (7)	0.0018 (8)
C15	0.0490 (11)	0.0444 (12)	0.0359 (9)	0.0057 (11)	0.0173 (9)	−0.0081 (9)
C16	0.0533 (12)	0.0482 (13)	0.0422 (10)	0.0127 (11)	0.0264 (9)	0.0016 (11)
C17	0.0426 (11)	0.0412 (12)	0.0630 (13)	0.0060 (10)	0.0331 (10)	−0.0001 (11)
C18	0.0453 (12)	0.0409 (11)	0.0363 (10)	0.0043 (9)	0.0093 (9)	0.0064 (9)
C19	0.0308 (8)	0.0320 (10)	0.0352 (9)	0.0006 (8)	0.0171 (7)	0.0054 (8)

Geometric parameters (Å, º) top

O1—C19	1.440 (2)	C8—H8A	0.9800
O1—C2	1.458 (3)	C9—C11	1.542 (2)
O2—C2	1.384 (3)	C9—C10	1.543 (2)
O2—H2A	0.8200	C9—H9	0.9800
O3—C3	1.429 (3)	C10—C19	1.545 (2)
O3—H3A	0.8200	C11—C12	1.533 (2)
O4—C16	1.214 (3)	C11—H11A	0.9700
C1—C2	1.512 (2)	C11—H11B	0.9700
C1—C10	1.528 (3)	C12—C13	1.519 (3)
C1—H1A	0.9700	C12—H12A	0.9700
C1—H1B	0.9700	C12—H12B	0.9700
C2—C3	1.529 (3)	C13—C18	1.527 (3)
C3—C4	1.521 (4)	C13—C17	1.532 (3)
C3—H3B	0.9800	C13—C14	1.539 (3)
C4—C5	1.537 (3)	C14—C15	1.532 (3)
C4—H4B	0.9700	C14—H14	0.9800
C4—H4C	0.9700	C15—C16	1.515 (3)
C5—C6	1.525 (3)	C15—H15A	0.9700
C5—C10	1.551 (2)	C15—H15B	0.9700
C5—H5A	0.9800	C16—C17	1.512 (4)
C6—C7	1.523 (3)	C17—H17A	0.9700
C6—H6A	0.9700	C17—H17B	0.9700
C6—H6B	0.9700	C18—H18A	0.9600
C7—C8	1.528 (2)	C18—H18B	0.9600
C7—H7A	0.9700	C18—H18C	0.9600
C7—H7B	0.9700	C19—H19A	0.9700
C8—C14	1.524 (2)	C19—H19B	0.9700
C8—C9	1.542 (3)

C19—O1—C2	109.44 (13)	C1—C10—C9	113.66 (15)
C2—O2—H2A	109.5	C1—C10—C19	100.18 (14)
C3—O3—H3A	109.5	C9—C10—C19	115.84 (14)
C2—C1—C10	101.51 (15)	C1—C10—C5	107.06 (15)
C2—C1—H1A	111.5	C9—C10—C5	109.94 (13)
C10—C1—H1A	111.5	C19—C10—C5	109.50 (15)
C2—C1—H1B	111.5	C12—C11—C9	113.59 (15)
C10—C1—H1B	111.5	C12—C11—H11A	108.8
H1A—C1—H1B	109.3	C9—C11—H11A	108.8
O2—C2—O1	108.94 (16)	C12—C11—H11B	108.8
O2—C2—C1	111.31 (17)	C9—C11—H11B	108.8
O1—C2—C1	103.11 (15)	H11A—C11—H11B	107.7
O2—C2—C3	114.50 (17)	C13—C12—C11	110.12 (16)
O1—C2—C3	107.03 (17)	C13—C12—H12A	109.6
C1—C2—C3	111.22 (16)	C11—C12—H12A	109.6
O3—C3—C4	111.86 (18)	C13—C12—H12B	109.6
O3—C3—C2	106.94 (18)	C11—C12—H12B	109.6
C4—C3—C2	109.48 (16)	H12A—C12—H12B	108.2
O3—C3—H3B	109.5	C12—C13—C18	110.98 (17)
C4—C3—H3B	109.5	C12—C13—C17	115.81 (17)
C2—C3—H3B	109.5	C18—C13—C17	107.28 (17)
C3—C4—C5	114.94 (17)	C12—C13—C14	108.43 (16)
C3—C4—H4B	108.5	C18—C13—C14	113.29 (16)
C5—C4—H4B	108.5	C17—C13—C14	100.79 (15)
C3—C4—H4C	108.5	C8—C14—C15	119.80 (17)
C5—C4—H4C	108.5	C8—C14—C13	113.53 (13)
H4B—C4—H4C	107.5	C15—C14—C13	103.60 (15)
C6—C5—C4	109.85 (17)	C8—C14—H14	106.3
C6—C5—C10	112.35 (16)	C15—C14—H14	106.3
C4—C5—C10	110.84 (14)	C13—C14—H14	106.3
C6—C5—H5A	107.9	C16—C15—C14	103.53 (19)
C4—C5—H5A	107.9	C16—C15—H15A	111.1
C10—C5—H5A	107.9	C14—C15—H15A	111.1
C7—C6—C5	112.59 (18)	C16—C15—H15B	111.1
C7—C6—H6A	109.1	C14—C15—H15B	111.1
C5—C6—H6A	109.1	H15A—C15—H15B	109.0
C7—C6—H6B	109.1	O4—C16—C17	125.6 (2)
C5—C6—H6B	109.1	O4—C16—C15	125.4 (3)
H6A—C6—H6B	107.8	C17—C16—C15	108.98 (18)
C6—C7—C8	111.69 (15)	C16—C17—C13	102.17 (17)
C6—C7—H7A	109.3	C16—C17—H17A	111.3
C8—C7—H7A	109.3	C13—C17—H17A	111.3
C6—C7—H7B	109.3	C16—C17—H17B	111.3
C8—C7—H7B	109.3	C13—C17—H17B	111.3
H7A—C7—H7B	107.9	H17A—C17—H17B	109.2
C14—C8—C7	111.37 (14)	C13—C18—H18A	109.5
C14—C8—C9	108.93 (15)	C13—C18—H18B	109.5
C7—C8—C9	109.80 (16)	H18A—C18—H18B	109.5
C14—C8—H8A	108.9	C13—C18—H18C	109.5
C7—C8—H8A	108.9	H18A—C18—H18C	109.5
C9—C8—H8A	108.9	H18B—C18—H18C	109.5
C8—C9—C11	112.89 (15)	O1—C19—C10	105.95 (16)
C8—C9—C10	111.57 (15)	O1—C19—H19A	110.5
C11—C9—C10	113.97 (14)	C10—C19—H19A	110.5
C8—C9—H9	105.9	O1—C19—H19B	110.5
C11—C9—H9	105.9	C10—C19—H19B	110.5
C10—C9—H9	105.9	H19A—C19—H19B	108.7

C19—O1—C2—O2	−142.16 (15)	C4—C5—C10—C1	−60.1 (2)
C19—O1—C2—C1	−23.84 (19)	C6—C5—C10—C9	52.7 (2)
C19—O1—C2—C3	93.54 (17)	C4—C5—C10—C9	176.02 (17)
C10—C1—C2—O2	158.11 (16)	C6—C5—C10—C19	−75.65 (19)
C10—C1—C2—O1	41.46 (17)	C4—C5—C10—C19	47.7 (2)
C10—C1—C2—C3	−72.9 (2)	C8—C9—C11—C12	50.3 (2)
O2—C2—C3—O3	64.1 (2)	C10—C9—C11—C12	178.96 (17)
O1—C2—C3—O3	−175.03 (16)	C9—C11—C12—C13	−54.3 (2)
C1—C2—C3—O3	−63.1 (2)	C11—C12—C13—C18	−67.1 (2)
O2—C2—C3—C4	−174.50 (18)	C11—C12—C13—C17	170.30 (18)
O1—C2—C3—C4	−53.7 (2)	C11—C12—C13—C14	57.9 (2)
C1—C2—C3—C4	58.3 (2)	C7—C8—C14—C15	−59.0 (2)
O3—C3—C4—C5	75.6 (2)	C9—C8—C14—C15	179.72 (16)
C2—C3—C4—C5	−42.7 (2)	C7—C8—C14—C13	177.94 (17)
C3—C4—C5—C6	169.86 (18)	C9—C8—C14—C13	56.7 (2)
C3—C4—C5—C10	45.1 (2)	C12—C13—C14—C8	−61.8 (2)
C4—C5—C6—C7	−176.24 (17)	C18—C13—C14—C8	61.8 (2)
C10—C5—C6—C7	−52.4 (2)	C17—C13—C14—C8	176.12 (17)
C5—C6—C7—C8	54.4 (3)	C12—C13—C14—C15	166.64 (15)
C6—C7—C8—C14	−177.36 (19)	C18—C13—C14—C15	−69.71 (19)
C6—C7—C8—C9	−56.6 (2)	C17—C13—C14—C15	44.6 (2)
C14—C8—C9—C11	−49.58 (18)	C8—C14—C15—C16	−156.82 (17)
C7—C8—C9—C11	−171.78 (16)	C13—C14—C15—C16	−29.09 (19)
C14—C8—C9—C10	−179.45 (14)	C14—C15—C16—O4	−179.7 (2)
C7—C8—C9—C10	58.35 (18)	C14—C15—C16—C17	2.5 (2)
C2—C1—C10—C9	−166.58 (15)	O4—C16—C17—C13	−152.8 (2)
C2—C1—C10—C19	−42.37 (17)	C15—C16—C17—C13	25.0 (2)
C2—C1—C10—C5	71.82 (17)	C12—C13—C17—C16	−158.74 (18)
C8—C9—C10—C1	−176.07 (14)	C18—C13—C17—C16	76.7 (2)
C11—C9—C10—C1	54.6 (2)	C14—C13—C17—C16	−42.0 (2)
C8—C9—C10—C19	68.68 (19)	C2—O1—C19—C10	−3.4 (2)
C11—C9—C10—C19	−60.6 (2)	C1—C10—C19—O1	28.71 (17)
C8—C9—C10—C5	−56.09 (19)	C9—C10—C19—O1	151.40 (15)
C11—C9—C10—C5	174.61 (17)	C5—C10—C19—O1	−83.62 (18)
C6—C5—C10—C1	176.60 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.82	2.03	2.8088 (19)	158

Symmetry code: (i) −x, y+1/2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₈O₄
M_r	320.41
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	295
a, b, c (Å)	10.8687 (2), 6.3379 (1), 12.9038 (2)
β (°)	112.882 (1)
V (Å³)	818.93 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	MAC DIP 2030K diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	2065, 2065, 1929
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.105, 1.14
No. of reflections	2065
No. of parameters	208
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.15

Computer programs: DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Selected geometric parameters (Å, º) top

O1—C19	1.440 (2)	O4—C16	1.214 (3)
O2—C2	1.384 (3)	C1—C2	1.512 (2)
O3—C3	1.429 (3)	C1—C10	1.528 (3)

C19—O1—C2	109.44 (13)	C6—C5—C4	109.85 (17)
C2—C1—C10	101.51 (15)	C12—C11—C9	113.59 (15)
O2—C2—O1	108.94 (16)	C18—C13—C17	107.28 (17)
O3—C3—C4	111.86 (18)	C17—C16—C15	108.98 (18)
C3—C4—C5	114.94 (17)

C19—O1—C2—O2	−142.16 (15)	C6—C7—C8—C9	−56.6 (2)
C10—C1—C2—O1	41.46 (17)	C10—C9—C11—C12	178.96 (17)
C1—C2—C3—O3	−63.1 (2)	C11—C12—C13—C18	−67.1 (2)
C3—C4—C5—C6	169.86 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O1ⁱ	0.82	2.03	2.8088 (19)	158.2

Symmetry code: (i) −x, y+1/2, −z+1.

Acknowledgements

We acknowledge financial support from the International Centre for Diffraction Data, Pennsylvania, USA.

References

Champagne, D. E., Koul, O., Isman, M. B., Scudder, G. G. E. & Towers, G. H. N. (1992). Phytochemistry, 31, 377–394. CrossRef CAS Web of Science Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Pupo, M. T., Vieira, P. C., Fernandes, J. B., da Silva, M. F. & Fo, R. E. (1997). Phytochemistry, 45, 1495–1500. CrossRef Web of Science Google Scholar
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