Eplerenone 1,4-dioxane solvate

Xu, L.-Z.; Yang, Q.; Nie, J.-J.

doi:10.1107/S1600536807060199

Eplerenone 1,4-dioxane solvate

Eplerenone is an aldosterone receptor antagonist. Single crystals of the title compound [systematic name: 9α,11-epoxy-7α-(methoxycarbonyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone dioxane solvate], C₂₄H₃₀O₆·C₄H₈O₂, were obtained from a dioxane solution. Within the eplerenone molecule, both five-membered rings display an envelope conformation. The three six-membered rings exhibit different conformations: chair, half-chair and envelope. In the crystal structure, adjacent eplerenone molecules are linked together via weak intermolecular C—H

O hydrogen bonding, forming a cavity of about 310 Å³, and the dioxane solvent molecules occupy the cavity. The solvent molecule is disordered equally over two positions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060199/xu2379sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060199/xu2379Isup2.hkl Contains datablock I

CCDC reference: 673081

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Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.006 Å
Disorder in main residue
R factor = 0.065
wR factor = 0.209
Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O71A   -   C71B    ..       7.81 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O71B   -   C71B    ..       8.28 su
PLAT230_ALERT_2_B Hirshfeld Test Diff for    O72B   -   C73B    ..       7.87 su

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       3.99
PLAT301_ALERT_3_C Main Residue  Disorder .........................      14.00 Perc.
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          6

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           27.42
           From the CIF: _reflns_number_total               3340
           Count of symmetry unique reflns         3352
           Completeness (_total/calc)             99.64%
           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 C8     ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9     ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    ...          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11    ...          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 C17    ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         12

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

   9 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
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

The eplerenone is known as an aldosterone receptor antagonist and can be administered in a therapeutically effective amount where use of an aldosterone receptor antagonist (Grob & Kalvoda, 1985). The crystal structure of the eplerenone with dioxane solvent is reported here.

The crystal of the title compound consists of eplerenone molecules and lattice dioxane moleuces as shown in Fig. 1. The molecule of eplerenone contains three fused six-membered rings, two five-membered rings and one three-membered ring. Both five-membered rings display the envelope configuration, similar to that found in the structure of eplerenone tetrahydrofuran solvate (Yang et al., 2007). The O5-carbonyl group of the C23-ester group forms an intra-molecular hydrogen bond with the adjacent C14-methine group (Fig. 1 and Table 1). This structural features is identical with that found in the crystal structure of eplerenone dichloromethane solvate (Grob et al., 1997).

In the crystal the adjacent eplerenone molecules are linked together via weak intermolecular C—H···O hydrogen bonding (Table 1), forming the 310 Å³ cavity (Spek, 2003), where the disordered dioxane solvent molecules occupied (Fig. 2).

Related literature top

For general background, see: Grob & Kalvoda (1985). For related structures, see: Grob et al. (1997); Yang et al. (2007).

For related literature, see: Spek (2003).

Experimental top

The eplerenone dichloromethane was prepared according to the procedure reported by Grob et al. (1997). The dichloromethane solvent was removed by heating at 363 K to get a powder crystalline sample. Single crystals of the title compound were crystallized from a dioxane solution of eplerenone at room temperature.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SIR92 (Altomare et al., 1993); 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 the title compound with 30% probability displacement (arbitrary spheres for H atoms). One of disordered dioxane components has been omitted for clarity. The dashed line indicates intramolecular hydrogen bongding.
	Fig. 2. The unit cell packing of the title compound. H atoms and one of disordered components have been omitted for clarity.

9α,11-Epoxy-7α-(methoxycarbonyl)-3-oxo-17α-pregn-4-ene-21,17-carbolactone dioxane solvate top

Crystal data top

C₂₄H₃₀O₆·C₄H₈O₂	F(000) = 1080
M_r = 502.58	D_x = 1.288 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 8986 reflections
a = 8.2308 (8) Å	θ = 3.0–25.5°
b = 13.5580 (12) Å	µ = 0.09 mm⁻¹
c = 23.2279 (18) Å	T = 291 K
V = 2592.1 (4) Å³	Prism, colorless
Z = 4	0.48 × 0.45 × 0.27 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2244 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.060
Graphite monochromator	θ_max = 27.4°, θ_min = 3.0°
Detector resolution: 10.0 pixels mm^-1	h = −10→9
ω scans	k = −17→17
24758 measured reflections	l = −29→30
3340 independent reflections

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)] = 0.065	H-atom parameters constrained
wR(F²) = 0.209	w = 1/[σ²(F_o²) + (0.1356P)²] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
3340 reflections	Δρ_max = 0.36 e Å⁻³
324 parameters	Δρ_min = −0.42 e Å⁻³
12 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.016 (4)

Crystal data top

C₂₄H₃₀O₆·C₄H₈O₂	V = 2592.1 (4) Å³
M_r = 502.58	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.2308 (8) Å	µ = 0.09 mm⁻¹
b = 13.5580 (12) Å	T = 291 K
c = 23.2279 (18) Å	0.48 × 0.45 × 0.27 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	2244 reflections with I > 2σ(I)
24758 measured reflections	R_int = 0.060
3340 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.065	12 restraints
wR(F²) = 0.209	H-atom parameters constrained
S = 1.07	Δρ_max = 0.36 e Å⁻³
3340 reflections	Δρ_min = −0.42 e Å⁻³
324 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	Occ. (<1)
O1	−0.0712 (5)	0.5542 (3)	0.10266 (16)	0.0857 (12)
O2	0.1407 (3)	0.82048 (19)	0.29115 (11)	0.0458 (6)
O3	0.4915 (4)	0.8356 (2)	0.49706 (11)	0.0573 (8)
O4	0.3797 (5)	0.8881 (3)	0.57887 (13)	0.0739 (10)
O5	0.4814 (6)	0.9205 (3)	0.22206 (16)	0.0855 (12)
O6	0.2938 (4)	0.8363 (2)	0.17302 (13)	0.0638 (9)
C1	−0.0097 (6)	0.5814 (3)	0.1479 (2)	0.0596 (11)
C2	0.1593 (6)	0.6089 (3)	0.15113 (19)	0.0548 (10)
H2	0.2196	0.6078	0.1173	0.066*
C3	0.2352 (5)	0.6361 (3)	0.19966 (18)	0.0494 (9)
C4	0.1465 (4)	0.6421 (3)	0.25689 (16)	0.0430 (8)
C5	−0.0358 (5)	0.6585 (4)	0.2456 (2)	0.0594 (11)
H5A	−0.0947	0.6521	0.2815	0.071*
H5B	−0.0521	0.7250	0.2314	0.071*
C6	−0.1048 (5)	0.5854 (4)	0.2021 (2)	0.0669 (13)
H6A	−0.1070	0.5202	0.2193	0.080*
H6B	−0.2159	0.6038	0.1931	0.080*
C7	0.4150 (5)	0.6551 (4)	0.19859 (17)	0.0526 (10)
H7A	0.4490	0.6648	0.1590	0.063*
H7B	0.4709	0.5973	0.2132	0.063*
C8	0.4663 (4)	0.7454 (3)	0.23433 (17)	0.0493 (10)
H8	0.5852	0.7445	0.2364	0.059*
C9	0.4029 (4)	0.7308 (3)	0.29600 (16)	0.0433 (8)
H9	0.4423	0.6663	0.3091	0.052*
C10	0.2189 (4)	0.7252 (3)	0.29489 (16)	0.0396 (8)
C11	0.1279 (5)	0.7654 (3)	0.34464 (16)	0.0446 (9)
H11	0.0218	0.7348	0.3514	0.054*
C12	0.2060 (5)	0.8094 (3)	0.39728 (17)	0.0472 (9)
H12A	0.1550	0.7820	0.4314	0.057*
H12B	0.1876	0.8800	0.3974	0.057*
C13	0.3889 (5)	0.7893 (3)	0.39967 (16)	0.0436 (9)
C14	0.4620 (4)	0.8068 (3)	0.33951 (16)	0.0439 (9)
H14	0.4279	0.8723	0.3263	0.053*
C15	0.6476 (5)	0.8095 (4)	0.3502 (2)	0.0625 (12)
H15A	0.6946	0.7443	0.3455	0.075*
H15B	0.7003	0.8545	0.3237	0.075*
C16	0.6669 (5)	0.8450 (4)	0.4121 (2)	0.0596 (11)
H16A	0.7288	0.9058	0.4133	0.072*
H16B	0.7229	0.7958	0.4350	0.072*
C17	0.4952 (5)	0.8617 (3)	0.43499 (15)	0.0481 (9)
C18	0.4392 (6)	0.9696 (3)	0.43506 (18)	0.0530 (10)
H18A	0.5318	1.0139	0.4349	0.064*
H18B	0.3724	0.9834	0.4016	0.064*
C19	0.3419 (6)	0.9810 (3)	0.48991 (17)	0.0593 (11)
H19A	0.3603	1.0453	0.5071	0.071*
H19B	0.2267	0.9731	0.4825	0.071*
C20	0.4042 (6)	0.9003 (3)	0.52813 (18)	0.0551 (10)
C21	0.1706 (6)	0.5435 (3)	0.2897 (2)	0.0604 (11)
H21A	0.1290	0.4901	0.2670	0.091*
H21B	0.1136	0.5462	0.3258	0.091*
H21C	0.2843	0.5333	0.2968	0.091*
C22	0.4163 (6)	0.6834 (3)	0.42091 (18)	0.0571 (11)
H22A	0.3896	0.6793	0.4611	0.086*
H22B	0.5282	0.6657	0.4155	0.086*
H22C	0.3484	0.6391	0.3995	0.086*
C23	0.4185 (6)	0.8438 (4)	0.20998 (18)	0.0558 (11)
C24	0.2338 (9)	0.9278 (4)	0.1488 (3)	0.0927 (19)
H24A	0.2996	0.9460	0.1164	0.139*
H24B	0.2388	0.9787	0.1775	0.139*
H24C	0.1233	0.9191	0.1366	0.139*
O71A	0.193 (2)	0.3566 (12)	0.4854 (9)	0.166 (4)	0.50
O72A	0.431 (2)	0.3198 (9)	0.4216 (7)	0.166 (4)	0.50
C71A	0.294 (3)	0.4369 (11)	0.4700 (7)	0.154 (3)	0.50
H71A	0.3886	0.4419	0.4946	0.185*	0.50
H71B	0.2350	0.4989	0.4703	0.185*	0.50
C72A	0.337 (3)	0.4045 (12)	0.4096 (6)	0.154 (3)	0.50
H72A	0.2413	0.3884	0.3872	0.185*	0.50
H72B	0.4000	0.4543	0.3896	0.185*	0.50
C73A	0.315 (3)	0.2469 (13)	0.4373 (7)	0.154 (3)	0.50
H73A	0.3591	0.1811	0.4325	0.185*	0.50
H73B	0.2172	0.2530	0.4142	0.185*	0.50
C74A	0.280 (3)	0.2688 (12)	0.5006 (7)	0.154 (3)	0.50
H74A	0.2126	0.2194	0.5190	0.185*	0.50
H74B	0.3772	0.2813	0.5231	0.185*	0.50
O71B	0.187 (2)	0.3779 (12)	0.4944 (8)	0.166 (4)	0.50
O72B	0.368 (2)	0.2869 (10)	0.3974 (6)	0.166 (4)	0.50
C71B	0.190 (4)	0.4141 (11)	0.4372 (7)	0.154 (3)	0.50
H71C	0.2779	0.4609	0.4330	0.185*	0.50
H71D	0.0886	0.4486	0.4295	0.185*	0.50
C72B	0.211 (2)	0.3308 (12)	0.3932 (7)	0.154 (3)	0.50
H72C	0.1285	0.2807	0.3998	0.185*	0.50
H72D	0.1953	0.3568	0.3547	0.185*	0.50
C73B	0.365 (4)	0.2373 (12)	0.4509 (6)	0.154 (3)	0.50
H73C	0.4686	0.2056	0.4589	0.185*	0.50
H73D	0.2796	0.1883	0.4521	0.185*	0.50
C74B	0.333 (3)	0.3201 (11)	0.4930 (7)	0.154 (3)	0.50
H74C	0.3443	0.2917	0.5311	0.185*	0.50
H74D	0.4216	0.3665	0.4885	0.185*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.087 (3)	0.097 (3)	0.073 (2)	−0.032 (2)	−0.019 (2)	−0.012 (2)
O2	0.0459 (13)	0.0406 (14)	0.0510 (14)	0.0051 (11)	−0.0005 (12)	0.0003 (12)
O3	0.0726 (18)	0.0561 (17)	0.0431 (14)	0.0134 (15)	−0.0107 (14)	0.0028 (13)
O4	0.108 (3)	0.069 (2)	0.0451 (17)	0.009 (2)	−0.0006 (18)	−0.0004 (15)
O5	0.106 (3)	0.070 (2)	0.081 (2)	−0.041 (2)	−0.002 (2)	0.0095 (18)
O6	0.072 (2)	0.0581 (18)	0.0613 (18)	−0.0009 (16)	−0.0077 (16)	0.0094 (15)
C1	0.063 (3)	0.046 (2)	0.069 (3)	−0.007 (2)	−0.005 (2)	−0.011 (2)
C2	0.057 (2)	0.058 (2)	0.050 (2)	−0.005 (2)	−0.004 (2)	−0.0102 (19)
C3	0.050 (2)	0.048 (2)	0.050 (2)	0.0030 (18)	0.0030 (19)	−0.0074 (19)
C4	0.0394 (18)	0.0406 (19)	0.049 (2)	0.0015 (15)	0.0054 (17)	−0.0026 (16)
C5	0.041 (2)	0.067 (3)	0.070 (3)	−0.001 (2)	−0.002 (2)	−0.016 (2)
C6	0.048 (2)	0.071 (3)	0.082 (3)	−0.008 (2)	0.003 (2)	−0.020 (3)
C7	0.0431 (19)	0.065 (3)	0.049 (2)	0.0012 (19)	0.0061 (18)	−0.009 (2)
C8	0.0374 (19)	0.062 (3)	0.049 (2)	−0.0047 (19)	0.0070 (17)	−0.0024 (18)
C9	0.0391 (17)	0.046 (2)	0.0448 (19)	0.0065 (16)	0.0011 (17)	−0.0005 (17)
C10	0.0363 (16)	0.0373 (18)	0.0450 (19)	0.0005 (14)	0.0055 (16)	0.0027 (16)
C11	0.0427 (19)	0.045 (2)	0.046 (2)	0.0004 (16)	0.0059 (17)	0.0015 (17)
C12	0.047 (2)	0.048 (2)	0.046 (2)	0.0015 (17)	0.0009 (18)	−0.0014 (18)
C13	0.047 (2)	0.045 (2)	0.0391 (18)	0.0044 (16)	−0.0018 (16)	0.0009 (16)
C14	0.0387 (18)	0.048 (2)	0.045 (2)	−0.0007 (16)	0.0033 (16)	−0.0016 (17)
C15	0.041 (2)	0.085 (3)	0.061 (3)	−0.003 (2)	−0.001 (2)	−0.008 (2)
C16	0.047 (2)	0.068 (3)	0.064 (3)	0.002 (2)	−0.008 (2)	−0.008 (2)
C17	0.058 (2)	0.048 (2)	0.0390 (19)	0.0053 (18)	−0.0067 (17)	0.0005 (16)
C18	0.060 (2)	0.045 (2)	0.054 (2)	−0.0058 (19)	−0.007 (2)	0.0038 (18)
C19	0.075 (3)	0.049 (2)	0.054 (2)	0.008 (2)	−0.009 (2)	−0.0017 (19)
C20	0.071 (3)	0.047 (2)	0.047 (2)	0.000 (2)	−0.002 (2)	−0.0025 (18)
C21	0.063 (3)	0.047 (2)	0.071 (3)	−0.006 (2)	0.001 (2)	0.004 (2)
C22	0.072 (3)	0.046 (2)	0.053 (2)	0.010 (2)	−0.001 (2)	0.0045 (19)
C23	0.056 (2)	0.065 (3)	0.046 (2)	−0.012 (2)	0.007 (2)	0.006 (2)
C24	0.124 (5)	0.076 (4)	0.078 (3)	0.023 (4)	−0.018 (4)	0.015 (3)
O71A	0.207 (6)	0.082 (6)	0.208 (8)	0.044 (4)	0.120 (5)	0.001 (5)
O72A	0.207 (6)	0.082 (6)	0.208 (8)	0.044 (4)	0.120 (5)	0.001 (5)
C71A	0.252 (10)	0.078 (4)	0.133 (5)	0.035 (6)	0.038 (6)	0.020 (4)
C72A	0.252 (10)	0.078 (4)	0.133 (5)	0.035 (6)	0.038 (6)	0.020 (4)
C73A	0.252 (10)	0.078 (4)	0.133 (5)	0.035 (6)	0.038 (6)	0.020 (4)
C74A	0.252 (10)	0.078 (4)	0.133 (5)	0.035 (6)	0.038 (6)	0.020 (4)
O71B	0.207 (6)	0.082 (6)	0.208 (8)	0.044 (4)	0.120 (5)	0.001 (5)
O72B	0.207 (6)	0.082 (6)	0.208 (8)	0.044 (4)	0.120 (5)	0.001 (5)
C71B	0.252 (10)	0.078 (4)	0.133 (5)	0.035 (6)	0.038 (6)	0.020 (4)
C72B	0.252 (10)	0.078 (4)	0.133 (5)	0.035 (6)	0.038 (6)	0.020 (4)
C73B	0.252 (10)	0.078 (4)	0.133 (5)	0.035 (6)	0.038 (6)	0.020 (4)
C74B	0.252 (10)	0.078 (4)	0.133 (5)	0.035 (6)	0.038 (6)	0.020 (4)

Geometric parameters (Å, º) top

O1—C1	1.224 (6)	C16—H16A	0.9700
O2—C10	1.445 (4)	C16—H16B	0.9700
O2—C11	1.453 (5)	C17—C18	1.534 (6)
O3—C20	1.344 (5)	C18—C19	1.513 (6)
O3—C17	1.485 (4)	C18—H18A	0.9700
O4—C20	1.207 (5)	C18—H18B	0.9700
O5—C23	1.195 (6)	C19—C20	1.500 (6)
O6—C23	1.342 (6)	C19—H19A	0.9700
O6—C24	1.448 (6)	C19—H19B	0.9700
C1—C2	1.442 (7)	C21—H21A	0.9600
C1—C6	1.483 (7)	C21—H21B	0.9600
C2—C3	1.341 (6)	C21—H21C	0.9600
C2—H2	0.9300	C22—H22A	0.9600
C3—C7	1.502 (6)	C22—H22B	0.9600
C3—C4	1.519 (5)	C22—H22C	0.9600
C4—C5	1.539 (5)	C24—H24A	0.9600
C4—C10	1.550 (5)	C24—H24B	0.9600
C4—C21	1.552 (6)	C24—H24C	0.9600
C5—C6	1.525 (6)	O71A—C71A	1.412 (10)
C5—H5A	0.9700	O71A—C74A	1.431 (10)
C5—H5B	0.9700	O72A—C72A	1.412 (10)
C6—H6A	0.9700	O72A—C73A	1.422 (10)
C6—H6B	0.9700	C71A—C72A	1.513 (10)
C7—C8	1.539 (6)	C71A—H71A	0.9700
C7—H7A	0.9700	C71A—H71B	0.9700
C7—H7B	0.9700	C72A—H72A	0.9700
C8—C23	1.501 (7)	C72A—H72B	0.9700
C8—C9	1.538 (5)	C73A—C74A	1.527 (10)
C8—H8	0.9800	C73A—H73A	0.9700
C9—C10	1.517 (5)	C73A—H73B	0.9700
C9—C14	1.524 (5)	C74A—H74A	0.9700
C9—H9	0.9800	C74A—H74B	0.9700
C10—C11	1.481 (5)	O71B—C71B	1.416 (10)
C11—C12	1.504 (5)	O71B—C74B	1.430 (10)
C11—H11	0.9800	O72B—C73B	1.414 (10)
C12—C13	1.531 (5)	O72B—C72B	1.431 (10)
C12—H12A	0.9700	C71B—C72B	1.532 (10)
C12—H12B	0.9700	C71B—H71C	0.9700
C13—C22	1.535 (6)	C71B—H71D	0.9700
C13—C14	1.540 (5)	C72B—H72C	0.9700
C13—C17	1.550 (6)	C72B—H72D	0.9700
C14—C15	1.548 (5)	C73B—C74B	1.512 (10)
C14—H14	0.9800	C73B—H73C	0.9700
C15—C16	1.524 (6)	C73B—H73D	0.9700
C15—H15A	0.9700	C74B—H74C	0.9700
C15—H15B	0.9700	C74B—H74D	0.9700
C16—C17	1.527 (6)

C10—O2—C11	61.4 (2)	C16—C17—C18	114.8 (4)
C20—O3—C17	112.1 (3)	O3—C17—C13	110.6 (3)
C23—O6—C24	116.4 (4)	C16—C17—C13	104.1 (3)
O1—C1—C2	121.4 (5)	C18—C17—C13	115.8 (3)
O1—C1—C6	121.4 (4)	C19—C18—C17	105.0 (3)
C2—C1—C6	117.1 (4)	C19—C18—H18A	110.8
C3—C2—C1	124.3 (4)	C17—C18—H18A	110.8
C3—C2—H2	117.8	C19—C18—H18B	110.8
C1—C2—H2	117.8	C17—C18—H18B	110.8
C2—C3—C7	119.5 (4)	H18A—C18—H18B	108.8
C2—C3—C4	121.8 (4)	C20—C19—C18	104.0 (4)
C7—C3—C4	118.6 (3)	C20—C19—H19A	111.0
C3—C4—C5	109.1 (3)	C18—C19—H19A	111.0
C3—C4—C10	110.7 (3)	C20—C19—H19B	111.0
C5—C4—C10	111.5 (3)	C18—C19—H19B	111.0
C3—C4—C21	108.8 (3)	H19A—C19—H19B	109.0
C5—C4—C21	109.4 (4)	O4—C20—O3	121.6 (4)
C10—C4—C21	107.3 (3)	O4—C20—C19	128.4 (4)
C6—C5—C4	112.5 (4)	O3—C20—C19	110.0 (3)
C6—C5—H5A	109.1	C4—C21—H21A	109.5
C4—C5—H5A	109.1	C4—C21—H21B	109.5
C6—C5—H5B	109.1	H21A—C21—H21B	109.5
C4—C5—H5B	109.1	C4—C21—H21C	109.5
H5A—C5—H5B	107.8	H21A—C21—H21C	109.5
C1—C6—C5	112.9 (4)	H21B—C21—H21C	109.5
C1—C6—H6A	109.0	C13—C22—H22A	109.5
C5—C6—H6A	109.0	C13—C22—H22B	109.5
C1—C6—H6B	109.0	H22A—C22—H22B	109.5
C5—C6—H6B	109.0	C13—C22—H22C	109.5
H6A—C6—H6B	107.8	H22A—C22—H22C	109.5
C3—C7—C8	113.5 (3)	H22B—C22—H22C	109.5
C3—C7—H7A	108.9	O5—C23—O6	123.2 (4)
C8—C7—H7A	108.9	O5—C23—C8	124.9 (4)
C3—C7—H7B	108.9	O6—C23—C8	112.0 (4)
C8—C7—H7B	108.9	O6—C24—H24A	109.5
H7A—C7—H7B	107.7	O6—C24—H24B	109.5
C23—C8—C9	112.2 (3)	H24A—C24—H24B	109.5
C23—C8—C7	115.6 (3)	O6—C24—H24C	109.5
C9—C8—C7	107.8 (3)	H24A—C24—H24C	109.5
C23—C8—H8	106.9	H24B—C24—H24C	109.5
C9—C8—H8	106.9	C71A—O71A—C74A	114.3 (16)
C7—C8—H8	106.9	C72A—O72A—C73A	104.3 (15)
C10—C9—C14	111.3 (3)	O71A—C71A—C72A	98.6 (15)
C10—C9—C8	109.2 (3)	O71A—C71A—H71A	112.1
C14—C9—C8	115.0 (3)	C72A—C71A—H71A	112.1
C10—C9—H9	107.0	O71A—C71A—H71B	112.1
C14—C9—H9	107.0	C72A—C71A—H71B	112.1
C8—C9—H9	107.0	H71A—C71A—H71B	109.7
O2—C10—C11	59.5 (2)	O72A—C72A—C71A	100.5 (12)
O2—C10—C9	113.7 (3)	O72A—C72A—H72A	111.7
C11—C10—C9	118.2 (3)	C71A—C72A—H72A	111.7
O2—C10—C4	116.4 (3)	O72A—C72A—H72B	111.7
C11—C10—C4	121.2 (3)	C71A—C72A—H72B	111.7
C9—C10—C4	115.4 (3)	H72A—C72A—H72B	109.4
O2—C11—C10	59.0 (2)	O72A—C73A—C74A	103.7 (15)
O2—C11—C12	117.4 (3)	O72A—C73A—H73A	111.0
C10—C11—C12	124.4 (3)	C74A—C73A—H73A	111.0
O2—C11—H11	114.8	O72A—C73A—H73B	111.0
C10—C11—H11	114.8	C74A—C73A—H73B	111.0
C12—C11—H11	114.8	H73A—C73A—H73B	109.0
C11—C12—C13	112.3 (3)	O71A—C74A—C73A	91.1 (14)
C11—C12—H12A	109.1	O71A—C74A—H74A	113.5
C13—C12—H12A	109.1	C73A—C74A—H74A	113.5
C11—C12—H12B	109.1	O71A—C74A—H74B	113.5
C13—C12—H12B	109.1	C73A—C74A—H74B	113.5
H12A—C12—H12B	107.9	H74A—C74A—H74B	110.8
C12—C13—C22	108.8 (4)	C71B—O71B—C74B	99.1 (16)
C12—C13—C14	108.9 (3)	C73B—O72B—C72B	103.9 (15)
C22—C13—C14	112.2 (3)	O71B—C71B—C72B	111.8 (15)
C12—C13—C17	117.5 (3)	O71B—C71B—H71C	109.3
C22—C13—C17	109.8 (3)	C72B—C71B—H71C	109.3
C14—C13—C17	99.3 (3)	O71B—C71B—H71D	109.3
C9—C14—C13	111.9 (3)	C72B—C71B—H71D	109.3
C9—C14—C15	115.9 (3)	H71C—C71B—H71D	107.9
C13—C14—C15	104.1 (3)	O72B—C72B—C71B	111.4 (16)
C9—C14—H14	108.2	O72B—C72B—H72C	109.3
C13—C14—H14	108.2	C71B—C72B—H72C	109.3
C15—C14—H14	108.2	O72B—C72B—H72D	109.3
C16—C15—C14	105.2 (4)	C71B—C72B—H72D	109.3
C16—C15—H15A	110.7	H72C—C72B—H72D	108.0
C14—C15—H15A	110.7	O72B—C73B—C74B	102.6 (13)
C16—C15—H15B	110.7	O72B—C73B—H73C	111.2
C14—C15—H15B	110.7	C74B—C73B—H73C	111.2
H15A—C15—H15B	108.8	O72B—C73B—H73D	111.2
C15—C16—C17	106.2 (3)	C74B—C73B—H73D	111.2
C15—C16—H16A	110.5	H73C—C73B—H73D	109.2
C17—C16—H16A	110.5	O71B—C74B—C73B	124.7 (19)
C15—C16—H16B	110.5	O71B—C74B—H74C	106.1
C17—C16—H16B	110.5	C73B—C74B—H74C	106.1
H16A—C16—H16B	108.7	O71B—C74B—H74D	106.1
O3—C17—C16	108.8 (3)	C73B—C74B—H74D	106.1
O3—C17—C18	102.7 (3)	H74C—C74B—H74D	106.3

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O72Bⁱ	0.97	2.59	3.370 (15)	137
C12—H12B···O1ⁱⁱ	0.97	2.55	3.500 (6)	167
C14—H14···O5	0.98	2.55	3.138 (5)	119
C18—H18A···O71Bⁱⁱⁱ	0.97	2.55	3.335 (18)	138
C19—H19B···O1ⁱⁱ	0.97	2.60	3.252 (6)	125
C21—H21C···O5^iv	0.96	2.50	3.326 (7)	144

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

Experimental details

Crystal data
Chemical formula	C₂₄H₃₀O₆·C₄H₈O₂
M_r	502.58
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	291
a, b, c (Å)	8.2308 (8), 13.5580 (12), 23.2279 (18)
V (Å³)	2592.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.48 × 0.45 × 0.27

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	24758, 3340, 2244
R_int	0.060
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.065, 0.209, 1.07
No. of reflections	3340
No. of parameters	324
No. of restraints	12
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.42

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···O72Bⁱ	0.97	2.59	3.370 (15)	137
C12—H12B···O1ⁱⁱ	0.97	2.55	3.500 (6)	167
C14—H14···O5	0.98	2.55	3.138 (5)	119
C18—H18A···O71Bⁱⁱⁱ	0.97	2.55	3.335 (18)	138
C19—H19B···O1ⁱⁱ	0.97	2.60	3.252 (6)	125
C21—H21C···O5^iv	0.96	2.50	3.326 (7)	144

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

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