3β,5α,15α-Trihydr­oxy-5-androsten-17-one dihydrate

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

doi:10.1107/S1600536807052336

3β,5α,15α-Trihydroxy-5-androsten-17-one dihydrate

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

In the steroid skeleton of the title compound, C₁₉H₂₈O₄·2H₂O, ring A assumes a slightly twisted chair conformation, ring C adopts a regular chair conformation, ring B adopts a half-chair conformation and ring D has a somewhat twisted envelope conformation. The crystal packing exhibits an extensive three-dimensional hydrogen-bonding network, formed by intermolecular O—H

O hydrogen bonds between the steroid and water molecules.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807052336/cv2322sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807052336/cv2322Isup2.hkl Contains datablock I

CCDC reference: 667449

checkCIF report

Key indicators

Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R factor = 0.036
wR factor = 0.099
Data-to-parameter ratio = 9.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              H2 O

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           27.49
           From the CIF: _reflns_number_total               2539
           Count of symmetry unique reflns         2552
           Completeness (_total/calc)             99.49%
           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 C7     = .          S
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    = .          S
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15    = .          S
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          7

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

   8 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
   1 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). The title compound, (I), as a key starting material for the synthesis of drospirenone, was obtained by biotransformation with Colletotrichum lini from dehydroepiandrosterone (DHEA) (Romano et al., 2006). We report here the crystal structure of (I).

In (I) (Fig. 1), ring A assumes a slightly twisty chair conformation and ring C takes a regular chair conformation. In ring B, atoms C8 and C9 deviate at 0.242 and -0.503 Å from the mean plane C5—C7/C10, respectively, thus ring B takes a half-chair conformation. Ring D has a somewhat twisty envelope conformation: atoms C13, C15, C16 and C17 are nearly coplanar and atom C14 deviates from their mean plane at 0.625 Å.

In the crystal (Fig. 2), the crystalline water molecules involved in the formation of hydrogen bonding. The intermolecular and intramolecular O—H···O hydrogen bonding are found in the crystal lattice (Table 1).

Related literature top

For related literature, see: Andrea et al. (2006); Muhn et al. (1995).

Experimental top

The title compound was obtained by biotransformation with Colletotrichum lini from dehydroepiandrosterone(DHEA) according to the literature method (Andrea et al., 2006). Dehydroepiandrosterone(DHEA) was kindly offered by Mr. Pan, Jiubang Chemistry Corp. Ltd., Shanghai, China. Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation from the mixture of tetrahydrofuran and H₂O (9:1).

Structure description top

For related literature, see: Andrea et al. (2006); Muhn et al. (1995).

Computing details top

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

Figures top

	Fig. 1. The structure of (I) with the atomic numbering and 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 bonding.

3β,5α,15α-Trihydroxy-5-androsten-17-one dihydrate top

Crystal data top

C₁₉H₂₈O₄·2H₂O	F(000) = 776
M_r = 356.45	D_x = 1.227 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4751 reflections
a = 6.0653 (8) Å	θ = 2.3–25.8°
b = 12.4906 (16) Å	µ = 0.09 mm⁻¹
c = 25.472 (3) Å	T = 296 K
V = 1929.8 (4) Å³	Block, colourless
Z = 4	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2539 independent reflections
Radiation source: fine-focus sealed tube	2289 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
φ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	h = −7→7
T_min = 0.975, T_max = 0.983	k = −16→12
12301 measured reflections	l = −33→32

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.099	w = 1/[σ²(F_o²) + (0.0532P)² + 0.2939P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2539 reflections	Δρ_max = 0.20 e Å⁻³
256 parameters	Δρ_min = −0.21 e Å⁻³
7 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.015 (2)

Crystal data top

C₁₉H₂₈O₄·2H₂O	V = 1929.8 (4) Å³
M_r = 356.45	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 6.0653 (8) Å	µ = 0.09 mm⁻¹
b = 12.4906 (16) Å	T = 296 K
c = 25.472 (3) Å	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker SMART APEXII CCD area-detector diffractometer	2539 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1997)	2289 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.983	R_int = 0.026
12301 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	7 restraints
wR(F²) = 0.099	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.20 e Å⁻³
2539 reflections	Δρ_min = −0.21 e Å⁻³
256 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	0.8995 (3)	0.83766 (13)	0.94606 (5)	0.0479 (4)
H1X	0.994 (5)	0.884 (2)	0.9523 (11)	0.083 (11)*
O2	1.0556 (3)	0.96442 (12)	0.69625 (6)	0.0464 (4)
H2X	1.048 (5)	0.9884 (19)	0.6657 (7)	0.060 (8)*
O3	0.8912 (4)	1.01700 (14)	0.59879 (6)	0.0725 (6)
H3X	0.904 (5)	1.054 (2)	0.5714 (8)	0.076 (9)*
O4	0.7005 (4)	0.68704 (14)	0.53143 (6)	0.0679 (5)
O5	0.0560 (3)	0.64593 (14)	0.98689 (6)	0.0547 (4)
H5X	0.027 (6)	0.7099 (16)	0.9776 (11)	0.078 (9)*
H5Y	0.166 (4)	0.657 (2)	1.0062 (10)	0.076 (10)*
O6	1.2334 (5)	0.9667 (2)	0.96135 (14)	0.1160 (11)
H6X	1.325 (7)	0.937 (4)	0.9813 (17)	0.174*
H6Y	1.258 (8)	1.0295 (17)	0.9615 (16)	0.129 (16)*
C1	0.7195 (4)	0.71106 (15)	0.81999 (8)	0.0434 (5)
H1A	0.6202	0.6519	0.8131	0.052*
H1B	0.8654	0.6896	0.8085	0.052*
C2	0.7263 (4)	0.73072 (17)	0.87909 (8)	0.0457 (5)
H2A	0.5794	0.7468	0.8919	0.055*
H2B	0.7791	0.6671	0.8970	0.055*
C3	0.8782 (3)	0.82337 (16)	0.89005 (7)	0.0401 (4)
H3	1.0238	0.8074	0.8753	0.048*
C4	0.7891 (4)	0.92309 (16)	0.86418 (7)	0.0437 (5)
H4A	0.8881	0.9825	0.8710	0.052*
H4B	0.6467	0.9405	0.8793	0.052*
C5	0.7647 (3)	0.90839 (14)	0.80534 (7)	0.0353 (4)
C6	0.8447 (4)	0.98109 (14)	0.77263 (7)	0.0395 (4)
H6	0.9146	1.0401	0.7874	0.047*
C7	0.8322 (3)	0.97645 (14)	0.71421 (7)	0.0370 (4)
H7	0.7756	1.0451	0.7014	0.044*
C8	0.6798 (3)	0.88707 (14)	0.69432 (7)	0.0338 (4)
H8	0.5267	0.9116	0.6970	0.041*
C9	0.7080 (3)	0.78640 (13)	0.72853 (7)	0.0332 (4)
H9	0.8660	0.7701	0.7284	0.040*
C10	0.6452 (3)	0.80810 (14)	0.78689 (7)	0.0348 (4)
C11	0.5923 (4)	0.68699 (16)	0.70619 (8)	0.0505 (5)
H11A	0.6357	0.6250	0.7266	0.061*
H11B	0.4342	0.6957	0.7101	0.061*
C12	0.6449 (4)	0.66589 (17)	0.64823 (8)	0.0512 (6)
H12A	0.7997	0.6478	0.6445	0.061*
H12B	0.5582	0.6058	0.6357	0.061*
C13	0.5931 (4)	0.76454 (16)	0.61572 (8)	0.0415 (5)
C14	0.7281 (3)	0.85949 (15)	0.63714 (7)	0.0349 (4)
H14	0.8819	0.8354	0.6367	0.042*
C15	0.7121 (4)	0.94462 (17)	0.59409 (8)	0.0465 (5)
H15	0.5715	0.9830	0.5965	0.056*
C16	0.7217 (5)	0.87818 (19)	0.54340 (8)	0.0547 (6)
H16A	0.6131	0.9035	0.5184	0.066*
H16B	0.8667	0.8831	0.5275	0.066*
C17	0.6729 (4)	0.76470 (18)	0.55922 (8)	0.0470 (5)
C18	0.3422 (4)	0.7862 (2)	0.61283 (10)	0.0593 (6)
H18A	0.2878	0.8033	0.6472	0.089*
H18B	0.2683	0.7236	0.5999	0.089*
H18C	0.3149	0.8452	0.5896	0.089*
C19	0.3950 (4)	0.8263 (2)	0.79409 (9)	0.0526 (6)
H19A	0.3456	0.8802	0.7700	0.079*
H19B	0.3662	0.8492	0.8294	0.079*
H19C	0.3177	0.7606	0.7874	0.079*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0535 (9)	0.0549 (9)	0.0352 (7)	−0.0040 (8)	−0.0004 (7)	0.0027 (6)
O2	0.0432 (8)	0.0525 (8)	0.0436 (7)	−0.0128 (7)	−0.0001 (7)	0.0049 (7)
O3	0.1036 (16)	0.0654 (10)	0.0484 (9)	−0.0366 (11)	−0.0181 (10)	0.0222 (8)
O4	0.0860 (14)	0.0634 (10)	0.0543 (9)	0.0029 (11)	0.0013 (10)	−0.0193 (8)
O5	0.0672 (12)	0.0499 (9)	0.0471 (8)	0.0059 (9)	−0.0137 (8)	−0.0068 (7)
O6	0.0978 (19)	0.0640 (14)	0.186 (3)	−0.0229 (14)	−0.069 (2)	0.0263 (16)
C1	0.0507 (12)	0.0330 (9)	0.0465 (10)	−0.0046 (9)	−0.0029 (10)	0.0049 (8)
C2	0.0508 (12)	0.0432 (11)	0.0430 (10)	−0.0027 (10)	−0.0013 (10)	0.0105 (8)
C3	0.0392 (10)	0.0455 (10)	0.0355 (9)	0.0018 (9)	0.0035 (8)	0.0009 (8)
C4	0.0549 (12)	0.0363 (9)	0.0399 (9)	0.0032 (9)	0.0030 (10)	−0.0026 (8)
C5	0.0380 (10)	0.0296 (8)	0.0383 (8)	0.0062 (8)	0.0009 (8)	−0.0011 (7)
C6	0.0502 (11)	0.0277 (8)	0.0408 (9)	−0.0020 (8)	−0.0053 (9)	−0.0021 (7)
C7	0.0437 (10)	0.0253 (8)	0.0420 (9)	−0.0008 (8)	−0.0021 (8)	0.0047 (7)
C8	0.0306 (9)	0.0316 (8)	0.0390 (8)	0.0019 (8)	−0.0012 (8)	0.0002 (7)
C9	0.0312 (9)	0.0295 (8)	0.0388 (9)	−0.0017 (7)	0.0011 (7)	0.0008 (7)
C10	0.0314 (9)	0.0331 (9)	0.0399 (9)	0.0001 (7)	0.0023 (8)	0.0030 (7)
C11	0.0635 (15)	0.0381 (10)	0.0498 (11)	−0.0165 (11)	0.0010 (11)	−0.0010 (9)
C12	0.0637 (15)	0.0365 (10)	0.0532 (11)	−0.0110 (10)	−0.0012 (11)	−0.0089 (9)
C13	0.0363 (10)	0.0434 (10)	0.0446 (10)	−0.0041 (9)	−0.0019 (9)	−0.0080 (8)
C14	0.0322 (9)	0.0351 (9)	0.0374 (8)	−0.0001 (8)	−0.0017 (8)	0.0005 (7)
C15	0.0548 (13)	0.0439 (11)	0.0409 (10)	−0.0010 (10)	−0.0081 (10)	0.0043 (8)
C16	0.0642 (15)	0.0610 (13)	0.0389 (10)	0.0004 (13)	−0.0021 (11)	−0.0008 (10)
C17	0.0408 (11)	0.0556 (12)	0.0447 (10)	0.0025 (10)	−0.0063 (9)	−0.0101 (9)
C18	0.0360 (11)	0.0793 (17)	0.0624 (13)	−0.0065 (12)	−0.0042 (10)	−0.0115 (13)
C19	0.0328 (10)	0.0746 (15)	0.0504 (12)	−0.0008 (11)	0.0051 (9)	0.0034 (11)

Geometric parameters (Å, º) top

O1—C3	1.443 (2)	C8—C14	1.525 (2)
O1—H1X	0.830 (18)	C8—C9	1.539 (2)
O2—C7	1.438 (3)	C8—H8	0.9800
O2—H2X	0.835 (16)	C9—C11	1.536 (3)
O3—C15	1.418 (3)	C9—C10	1.558 (2)
O3—H3X	0.844 (17)	C9—H9	0.9800
O4—C17	1.212 (3)	C10—C19	1.546 (3)
O5—H5X	0.852 (18)	C11—C12	1.533 (3)
O5—H5Y	0.841 (18)	C11—H11A	0.9700
O6—H6X	0.84 (2)	C11—H11B	0.9700
O6—H6Y	0.799 (19)	C12—C13	1.518 (3)
C1—C2	1.526 (3)	C12—H12A	0.9700
C1—C10	1.544 (3)	C12—H12B	0.9700
C1—H1A	0.9700	C13—C17	1.518 (3)
C1—H1B	0.9700	C13—C14	1.541 (3)
C2—C3	1.505 (3)	C13—C18	1.547 (3)
C2—H2A	0.9700	C14—C15	1.531 (3)
C2—H2B	0.9700	C14—H14	0.9800
C3—C4	1.509 (3)	C15—C16	1.536 (3)
C3—H3	0.9800	C15—H15	0.9800
C4—C5	1.517 (3)	C16—C17	1.503 (3)
C4—H4A	0.9700	C16—H16A	0.9700
C4—H4B	0.9700	C16—H16B	0.9700
C5—C6	1.324 (3)	C18—H18A	0.9599
C5—C10	1.521 (3)	C18—H18B	0.9599
C6—C7	1.491 (2)	C18—H18C	0.9599
C6—H6	0.9300	C19—H19A	0.9599
C7—C8	1.536 (3)	C19—H19B	0.9599
C7—H7	0.9800	C19—H19C	0.9599

C3—O1—H1X	110 (2)	C1—C10—C19	109.70 (18)
C7—O2—H2X	102 (2)	C5—C10—C9	108.76 (15)
C15—O3—H3X	111 (2)	C1—C10—C9	108.25 (15)
H5X—O5—H5Y	100 (3)	C19—C10—C9	112.24 (16)
H6X—O6—H6Y	108 (5)	C12—C11—C9	113.61 (17)
C2—C1—C10	114.86 (16)	C12—C11—H11A	108.8
C2—C1—H1A	108.6	C9—C11—H11A	108.8
C10—C1—H1A	108.6	C12—C11—H11B	108.8
C2—C1—H1B	108.6	C9—C11—H11B	108.8
C10—C1—H1B	108.6	H11A—C11—H11B	107.7
H1A—C1—H1B	107.5	C13—C12—C11	110.04 (17)
C3—C2—C1	108.85 (16)	C13—C12—H12A	109.7
C3—C2—H2A	109.9	C11—C12—H12A	109.7
C1—C2—H2A	109.9	C13—C12—H12B	109.7
C3—C2—H2B	109.9	C11—C12—H12B	109.7
C1—C2—H2B	109.9	H12A—C12—H12B	108.2
H2A—C2—H2B	108.3	C12—C13—C17	116.87 (18)
O1—C3—C2	109.45 (16)	C12—C13—C14	108.75 (16)
O1—C3—C4	111.19 (16)	C17—C13—C14	99.50 (17)
C2—C3—C4	109.54 (17)	C12—C13—C18	111.8 (2)
O1—C3—H3	108.9	C17—C13—C18	105.57 (19)
C2—C3—H3	108.9	C14—C13—C18	113.90 (19)
C4—C3—H3	108.9	C8—C14—C15	121.00 (16)
C3—C4—C5	111.50 (15)	C8—C14—C13	114.19 (16)
C3—C4—H4A	109.3	C15—C14—C13	104.31 (15)
C5—C4—H4A	109.3	C8—C14—H14	105.3
C3—C4—H4B	109.3	C15—C14—H14	105.3
C5—C4—H4B	109.3	C13—C14—H14	105.3
H4A—C4—H4B	108.0	O3—C15—C14	109.50 (17)
C6—C5—C4	120.17 (17)	O3—C15—C16	112.7 (2)
C6—C5—C10	123.01 (17)	C14—C15—C16	102.98 (17)
C4—C5—C10	116.82 (16)	O3—C15—H15	110.5
C5—C6—C7	125.63 (18)	C14—C15—H15	110.5
C5—C6—H6	117.2	C16—C15—H15	110.5
C7—C6—H6	117.2	C17—C16—C15	106.06 (17)
O2—C7—C6	105.89 (17)	C17—C16—H16A	110.5
O2—C7—C8	112.73 (15)	C15—C16—H16A	110.5
C6—C7—C8	112.84 (16)	C17—C16—H16B	110.5
O2—C7—H7	108.4	C15—C16—H16B	110.5
C6—C7—H7	108.4	H16A—C16—H16B	108.7
C8—C7—H7	108.4	O4—C17—C16	124.8 (2)
C14—C8—C7	111.32 (15)	O4—C17—C13	126.6 (2)
C14—C8—C9	109.55 (14)	C16—C17—C13	108.55 (17)
C7—C8—C9	109.88 (14)	C13—C18—H18A	109.5
C14—C8—H8	108.7	C13—C18—H18B	109.5
C7—C8—H8	108.7	H18A—C18—H18B	109.5
C9—C8—H8	108.7	C13—C18—H18C	109.5
C11—C9—C8	113.58 (15)	H18A—C18—H18C	109.5
C11—C9—C10	112.49 (15)	H18B—C18—H18C	109.5
C8—C9—C10	111.77 (14)	C10—C19—H19A	109.5
C11—C9—H9	106.1	C10—C19—H19B	109.5
C8—C9—H9	106.1	H19A—C19—H19B	109.5
C10—C9—H9	106.1	C10—C19—H19C	109.5
C5—C10—C1	109.81 (15)	H19A—C19—H19C	109.5
C5—C10—C19	108.07 (17)	H19B—C19—H19C	109.5

C10—C1—C2—C3	−57.6 (3)	C11—C9—C10—C19	−59.7 (2)
C1—C2—C3—O1	−175.65 (17)	C8—C9—C10—C19	69.4 (2)
C1—C2—C3—C4	62.2 (2)	C8—C9—C11—C12	49.8 (3)
O1—C3—C4—C5	−179.56 (18)	C10—C9—C11—C12	178.05 (18)
C2—C3—C4—C5	−58.5 (2)	C9—C11—C12—C13	−54.7 (3)
C3—C4—C5—C6	−130.8 (2)	C11—C12—C13—C17	169.47 (19)
C3—C4—C5—C10	49.5 (3)	C11—C12—C13—C14	57.9 (2)
C4—C5—C6—C7	179.9 (2)	C11—C12—C13—C18	−68.7 (2)
C10—C5—C6—C7	−0.3 (3)	C7—C8—C14—C15	−58.5 (2)
C5—C6—C7—O2	−113.7 (2)	C9—C8—C14—C15	179.81 (17)
C5—C6—C7—C8	10.1 (3)	C7—C8—C14—C13	175.67 (16)
O2—C7—C8—C14	−40.9 (2)	C9—C8—C14—C13	53.9 (2)
C6—C7—C8—C14	−160.83 (17)	C12—C13—C14—C8	−60.2 (2)
O2—C7—C8—C9	80.62 (19)	C17—C13—C14—C8	177.07 (16)
C6—C7—C8—C9	−39.3 (2)	C18—C13—C14—C8	65.2 (2)
C14—C8—C9—C11	−47.6 (2)	C12—C13—C14—C15	165.60 (17)
C7—C8—C9—C11	−170.19 (16)	C17—C13—C14—C15	42.9 (2)
C14—C8—C9—C10	−176.18 (15)	C18—C13—C14—C15	−69.0 (2)
C7—C8—C9—C10	61.2 (2)	C8—C14—C15—O3	72.0 (2)
C6—C5—C10—C1	138.4 (2)	C13—C14—C15—O3	−157.68 (18)
C4—C5—C10—C1	−41.8 (2)	C8—C14—C15—C16	−167.8 (2)
C6—C5—C10—C19	−101.9 (2)	C13—C14—C15—C16	−37.5 (2)
C4—C5—C10—C19	77.8 (2)	O3—C15—C16—C17	134.6 (2)
C6—C5—C10—C9	20.2 (3)	C14—C15—C16—C17	16.7 (3)
C4—C5—C10—C9	−160.08 (17)	C15—C16—C17—O4	−167.5 (2)
C2—C1—C10—C5	46.0 (2)	C15—C16—C17—C13	10.4 (3)
C2—C1—C10—C19	−72.6 (2)	C12—C13—C17—O4	28.5 (3)
C2—C1—C10—C9	164.65 (18)	C14—C13—C17—O4	145.3 (2)
C11—C9—C10—C5	−179.26 (16)	C18—C13—C17—O4	−96.5 (3)
C8—C9—C10—C5	−50.1 (2)	C12—C13—C17—C16	−149.3 (2)
C11—C9—C10—C1	61.5 (2)	C14—C13—C17—C16	−32.6 (2)
C8—C9—C10—C1	−169.36 (16)	C18—C13—C17—C16	85.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1X···O6	0.83 (2)	1.80 (2)	2.618 (3)	170 (3)
O2—H2X···O3	0.84 (2)	1.98 (2)	2.755 (2)	153 (3)
O3—H3X···O5ⁱ	0.84 (2)	1.89 (2)	2.731 (2)	176 (3)
O5—H5X···O1ⁱⁱ	0.85 (2)	1.95 (2)	2.778 (2)	165 (3)
O5—H5Y···O1ⁱⁱⁱ	0.84 (2)	1.87 (2)	2.702 (2)	172 (3)
O6—H6X···O5^iv	0.84 (2)	1.92 (2)	2.747 (3)	168 (5)
O6—H6Y···O4^v	0.80 (2)	1.99 (2)	2.787 (3)	174 (5)

Symmetry codes: (i) −x+1, y+1/2, −z+3/2; (ii) x−1, y, z; (iii) x−1/2, −y+3/2, −z+2; (iv) x+3/2, −y+3/2, −z+2; (v) −x+2, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₈O₄·2H₂O
M_r	356.45
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	6.0653 (8), 12.4906 (16), 25.472 (3)
V (Å³)	1929.8 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1997)
T_min, T_max	0.975, 0.983
No. of measured, independent and observed [I > 2σ(I)] reflections	12301, 2539, 2289
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.099, 1.03
No. of reflections	2539
No. of parameters	256
No. of restraints	7
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.21

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997).