Eplerenone ethanol solvate

Yang, Q.; Ye, W.-D.; Yuan, J.-Y.; Nie, J.-J.; Xu, D.-J.

doi:10.1107/S1600536808009240

organic compounds

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ISSN: 2056-9890

Volume 64| Part 5| May 2008| Page o829

doi:10.1107/S1600536808009240

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Eplerenone ethanol solvate

Qian Yang,^a Wei-Dong Ye,^b Jian-Yong Yuan,^b Jing-Jing Nie ^a and Duan-Jun Xu ^a ^*

^aDepartment of Chemistry, Zhejiang University, Hangzhou 310027, People's Republic of China, and ^bXinchang Pharmaceutical Factory, Xinchang 312500, People's Republic of China
^*Correspondence e-mail: xudj@mail.hz.zj.cn

(Received 1 April 2008; accepted 5 April 2008; online 10 April 2008)

Eplerenone [systematic name: 7α-(methoxycarbonyl)-3-oxo-9α,11-epoxy-17α-pregn-4-ene-21,17-carbolactone], an aldosterone receptor antagonist, crystallizes from ethanol as a monosolvate, C₂₄H₃₀O₆·C₂H₆O. The eplerenone molecule has two five-membered rings, three six-membered rings and one three-membered ring. Both five-membered rings display envelope conformations, while the three six-membered rings assume envelope (cyclohexene), half-chair (cyclohexane sharing one edge with epoxy) and chair (other cyclohexane) conformations. The solvent molecule is disordered equally over two sites. It is linked to the eplerenone molecule by hydrogen bonds.

Related literature

For background literature, see: Grob et al. (1985 ). For related structures, see: Grob et al. (1997 ); Yang et al. (2007 ); Xu et al. (2007 ). For ring analysis, see: Spek (2003 ).

Experimental

Crystal data

C₂₄H₃₀O₆·C₂H₆O
M_r = 460.55
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.3236 (5) Å
b = 12.8306 (9) Å
c = 23.3173 (13) Å
V = 2490.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 (2) K
0.20 × 0.16 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: none
19548 measured reflections
2559 independent reflections
1955 reflections with I > 2σ(I)
R_int = 0.053

Refinement

R[F² > 2σ(F²)] = 0.056
wR(F²) = 0.151
S = 1.05
2559 reflections
293 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8A⋯O1ⁱ	0.96	2.19	3.15 (4)	178
O9—H9A⋯O1ⁱ	0.98	2.34	3.32 (4)	177
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, -z]$ .

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; 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, 2008 ); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808009240/ng2439sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808009240/ng2439Isup2.hkl

checkCIF report

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 et al., 1985). The crystal structure of the eplerenone ethanol solvate is reported here.

The crystal of the title compound consists of eplerenone molecules and lattice ethanol molecules (Fig. 1). The molecule of eplerenone contains three six-membered rings, two five-membered rings and one three-membered ring. A ring analysis (Spek, 2003) indicates that three six-membered rings assume different conformations: chair, half-chair and envelope; both five-membered rings display the similar envelope configuration. This agrees with those found in the structure of eplerenone THF solvate (Yang et al. 2007) and in the structure of eplerenone dioxane solvate (Xu et al., 2007). The C2—C3 bond distance of 1.343 (6) Å indicates the typical C?C double bond. The C23-ester group forms an intra-molecular C—H···O hydrogen bond with the adjacent C14-methine group (Table 1). This structural feature is also found in the crystal structure of eplerenone dichloromethane solvate (Grob et al., 1997).

In the crystal structure, lattice solvent molecules are disorderly located in the cavities formed by eplerenone molecules and link with eplerenone molecules via O—H···O and C—H···O hydrogen bonding (Table 1).

Related literature top

For background literature, see: Grob et al. (1985). For related structures, see: Grob et al. (1997); Yang et al. (2007); Xu et al. (2007). For ring analysis, see: Spek (2003).

Experimental top

A microcrystalline powder sample of eplerenone was prepared in the manner reported by Grob et al. (1997). Single crystals of the title compound were obtained from an ethanol solution of eplerenone.

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, 2008); 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 solvent components has been omitted for clarity.

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

Crystal data top

C₂₄H₃₀O₆·C₂H₆O	F(000) = 992
M_r = 460.55	D_x = 1.228 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4788 reflections
a = 8.3236 (5) Å	θ = 3.2–25.2°
b = 12.8306 (9) Å	µ = 0.09 mm⁻¹
c = 23.3173 (13) Å	T = 295 K
V = 2490.2 (3) Å³	Prism, colorless
Z = 4	0.20 × 0.16 × 0.14 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	1955 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 25.2°, θ_min = 3.0°
ω scans	h = −9→8
19548 measured reflections	k = −15→15
2559 independent reflections	l = −27→27

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.0933P)² + 0.2684P] where P = (F_o² + 2F_c²)/3
2559 reflections	(Δ/σ)_max = 0.002
293 parameters	Δρ_max = 0.30 e Å⁻³
6 restraints	Δρ_min = −0.19 e Å⁻³

Crystal data top

C₂₄H₃₀O₆·C₂H₆O	V = 2490.2 (3) Å³
M_r = 460.55	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.3236 (5) Å	µ = 0.09 mm⁻¹
b = 12.8306 (9) Å	T = 295 K
c = 23.3173 (13) Å	0.20 × 0.16 × 0.14 mm

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	1955 reflections with I > 2σ(I)
19548 measured reflections	R_int = 0.054
2559 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.056	6 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.05	Δρ_max = 0.30 e Å⁻³
2559 reflections	Δρ_min = −0.19 e Å⁻³
293 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	−0.0903 (5)	0.5823 (4)	0.10016 (17)	0.1137 (15)
O2	0.1457 (3)	0.82438 (19)	0.29175 (10)	0.0474 (6)
O3	0.4884 (4)	0.8328 (2)	0.49749 (10)	0.0644 (8)
O4	0.3946 (5)	0.8951 (3)	0.57892 (12)	0.0842 (10)
O5	0.4856 (5)	0.9197 (3)	0.22555 (13)	0.0866 (11)
O6	0.3136 (4)	0.8354 (2)	0.17081 (12)	0.0691 (8)
C1	−0.0244 (6)	0.5948 (4)	0.1464 (2)	0.0742 (13)
C2	0.1457 (6)	0.6130 (3)	0.15092 (19)	0.0642 (11)
H2	0.2062	0.6122	0.1174	0.077*
C3	0.2222 (5)	0.6310 (3)	0.20064 (16)	0.0476 (9)
C4	0.1357 (4)	0.6367 (3)	0.25779 (16)	0.0481 (9)
C5	−0.0438 (4)	0.6600 (4)	0.2471 (2)	0.0653 (11)
H5A	−0.1024	0.6499	0.2826	0.078*
H5B	−0.0552	0.7326	0.2361	0.078*
C6	−0.1187 (6)	0.5921 (4)	0.2008 (2)	0.0759 (13)
H6A	−0.1249	0.5208	0.2145	0.091*
H6B	−0.2272	0.6160	0.1933	0.091*
C7	0.4024 (4)	0.6423 (3)	0.20023 (16)	0.0515 (9)
H7A	0.4385	0.6512	0.1610	0.062*
H7B	0.4502	0.5787	0.2149	0.062*
C8	0.4618 (4)	0.7341 (3)	0.23596 (14)	0.0465 (9)
H8	0.5790	0.7285	0.2383	0.056*
C9	0.3961 (4)	0.7217 (3)	0.29729 (14)	0.0432 (8)
H9	0.4299	0.6526	0.3105	0.052*
C10	0.2131 (4)	0.7204 (3)	0.29597 (15)	0.0438 (8)
C11	0.1258 (4)	0.7665 (3)	0.34520 (16)	0.0467 (9)
H11	0.0178	0.7384	0.3516	0.056*
C12	0.2055 (4)	0.8119 (3)	0.39783 (15)	0.0508 (9)
H12A	0.1525	0.7852	0.4318	0.061*
H12B	0.1925	0.8871	0.3975	0.061*
C13	0.3852 (5)	0.7856 (3)	0.40082 (14)	0.0474 (9)
C14	0.4600 (4)	0.7996 (3)	0.34071 (14)	0.0451 (9)
H14	0.4309	0.8694	0.3271	0.054*
C15	0.6431 (5)	0.7989 (4)	0.35129 (17)	0.0646 (12)
H15A	0.6865	0.7293	0.3463	0.078*
H15B	0.6972	0.8458	0.3250	0.078*
C16	0.6647 (5)	0.8359 (5)	0.41383 (17)	0.0721 (13)
H16A	0.7153	0.7820	0.4368	0.086*
H16B	0.7307	0.8981	0.4153	0.086*
C17	0.4943 (5)	0.8590 (3)	0.43599 (14)	0.0534 (10)
C18	0.4499 (5)	0.9740 (3)	0.43479 (17)	0.0578 (10)
H18A	0.3843	0.9900	0.4015	0.069*
H18B	0.5455	1.0173	0.4339	0.069*
C19	0.3553 (7)	0.9913 (4)	0.49035 (16)	0.0727 (13)
H19A	0.3789	1.0590	0.5069	0.087*
H19B	0.2406	0.9858	0.4837	0.087*
C20	0.4135 (6)	0.9058 (3)	0.52799 (16)	0.0629 (11)
C21	0.1522 (6)	0.5303 (3)	0.28953 (19)	0.0659 (11)
H21A	0.2639	0.5144	0.2949	0.099*
H21B	0.1027	0.4765	0.2671	0.099*
H21C	0.1002	0.5346	0.3262	0.099*
C22	0.4032 (6)	0.6722 (3)	0.42265 (17)	0.0648 (11)
H22A	0.3698	0.6684	0.4620	0.097*
H22B	0.5135	0.6511	0.4196	0.097*
H22C	0.3374	0.6268	0.3999	0.097*
C23	0.4237 (5)	0.8399 (3)	0.21110 (15)	0.0503 (9)
C24	0.2627 (8)	0.9320 (4)	0.1450 (2)	0.0944 (18)
H24A	0.2670	0.9867	0.1731	0.142*
H24B	0.1546	0.9249	0.1312	0.142*
H24C	0.3326	0.9489	0.1136	0.142*
O8	0.547 (6)	0.823 (3)	0.0144 (17)	0.431 (13)*	0.50
H8A	0.5024	0.8527	−0.0201	0.646*	0.50
C81	0.715 (6)	0.815 (6)	0.021 (2)	0.431 (13)*	0.50
H81A	0.7682	0.8468	−0.0114	0.517*	0.50
H81B	0.7455	0.7423	0.0227	0.517*	0.50
C82	0.769 (7)	0.868 (5)	0.075 (2)	0.431 (13)*	0.50
H82A	0.8188	0.8181	0.1000	0.646*	0.50
H82B	0.6778	0.8983	0.0940	0.646*	0.50
H82C	0.8447	0.9219	0.0657	0.646*	0.50
O9	0.632 (5)	0.917 (4)	0.0182 (15)	0.431 (13)*	0.50
H9A	0.5650	0.9195	−0.0163	0.646*	0.50
C91	0.625 (7)	0.824 (4)	0.050 (3)	0.431 (13)*	0.50
H91A	0.6519	0.7660	0.0249	0.517*	0.50
H91B	0.5155	0.8136	0.0632	0.517*	0.50
C92	0.735 (7)	0.825 (5)	0.100 (2)	0.431 (13)*	0.50
H92A	0.7614	0.7541	0.1100	0.646*	0.50
H92B	0.6839	0.8584	0.1315	0.646*	0.50
H92C	0.8316	0.8614	0.0898	0.646*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.100 (3)	0.143 (4)	0.098 (3)	−0.039 (3)	−0.033 (2)	−0.015 (3)
O2	0.0473 (14)	0.0399 (13)	0.0551 (13)	0.0060 (11)	0.0018 (12)	0.0004 (11)
O3	0.091 (2)	0.0635 (17)	0.0388 (13)	0.0233 (17)	−0.0092 (14)	−0.0007 (13)
O4	0.127 (3)	0.079 (2)	0.0468 (16)	0.021 (2)	0.0019 (18)	0.0003 (15)
O5	0.114 (3)	0.072 (2)	0.0730 (19)	−0.039 (2)	−0.005 (2)	0.0047 (17)
O6	0.087 (2)	0.0521 (17)	0.0681 (16)	−0.0022 (17)	−0.0233 (16)	0.0092 (14)
C1	0.070 (3)	0.068 (3)	0.084 (3)	−0.016 (2)	−0.015 (3)	−0.018 (3)
C2	0.070 (3)	0.062 (3)	0.061 (2)	−0.006 (2)	−0.003 (2)	−0.011 (2)
C3	0.053 (2)	0.0314 (18)	0.058 (2)	0.0005 (16)	0.0028 (19)	−0.0040 (16)
C4	0.0421 (18)	0.041 (2)	0.062 (2)	0.0008 (16)	0.0030 (18)	−0.0031 (16)
C5	0.045 (2)	0.060 (3)	0.091 (3)	−0.001 (2)	−0.001 (2)	−0.023 (2)
C6	0.053 (2)	0.063 (3)	0.112 (4)	−0.009 (2)	−0.008 (3)	−0.023 (3)
C7	0.052 (2)	0.054 (2)	0.0484 (19)	0.0091 (18)	0.0050 (18)	−0.0047 (18)
C8	0.0345 (18)	0.061 (2)	0.0443 (19)	0.0012 (17)	0.0017 (16)	−0.0036 (17)
C9	0.0380 (17)	0.047 (2)	0.0443 (17)	0.0067 (15)	0.0050 (16)	0.0000 (16)
C10	0.0453 (18)	0.0397 (19)	0.0464 (18)	0.0024 (16)	0.0052 (17)	0.0026 (16)
C11	0.0408 (19)	0.042 (2)	0.057 (2)	0.0010 (16)	0.0100 (17)	0.0014 (17)
C12	0.054 (2)	0.052 (2)	0.0461 (18)	0.0068 (19)	0.0109 (18)	−0.0004 (17)
C13	0.052 (2)	0.052 (2)	0.0380 (17)	0.0077 (17)	0.0021 (17)	−0.0009 (16)
C14	0.0380 (18)	0.058 (2)	0.0397 (17)	0.0012 (17)	0.0022 (15)	0.0004 (16)
C15	0.045 (2)	0.095 (4)	0.054 (2)	0.007 (2)	−0.0038 (19)	−0.012 (2)
C16	0.053 (2)	0.103 (4)	0.060 (2)	0.017 (3)	−0.010 (2)	−0.016 (3)
C17	0.063 (2)	0.060 (2)	0.0365 (17)	0.008 (2)	−0.0021 (17)	0.0003 (17)
C18	0.066 (3)	0.056 (2)	0.051 (2)	−0.001 (2)	−0.0043 (19)	0.0061 (19)
C19	0.105 (4)	0.061 (3)	0.052 (2)	0.016 (3)	−0.004 (2)	0.000 (2)
C20	0.086 (3)	0.059 (3)	0.043 (2)	0.010 (2)	−0.005 (2)	−0.0002 (19)
C21	0.071 (3)	0.048 (2)	0.079 (3)	−0.001 (2)	0.014 (2)	0.005 (2)
C22	0.088 (3)	0.056 (2)	0.051 (2)	0.017 (2)	0.004 (2)	0.0080 (19)
C23	0.053 (2)	0.055 (2)	0.0424 (18)	−0.0129 (19)	0.0082 (17)	−0.0015 (17)
C24	0.122 (5)	0.071 (3)	0.090 (3)	0.020 (3)	−0.018 (3)	0.018 (3)

Geometric parameters (Å, º) top

O1—C1	1.221 (6)	C14—C15	1.545 (5)
O2—C10	1.451 (4)	C14—H14	0.9800
O2—C11	1.460 (4)	C15—C16	1.544 (6)
O3—C20	1.331 (5)	C15—H15A	0.9700
O3—C17	1.474 (4)	C15—H15B	0.9700
O4—C20	1.206 (5)	C16—C17	1.538 (6)
O5—C23	1.195 (5)	C16—H16A	0.9700
O6—C23	1.314 (5)	C16—H16B	0.9700
O6—C24	1.441 (5)	C17—C18	1.522 (6)
C1—C2	1.438 (7)	C18—C19	1.532 (6)
C1—C6	1.492 (7)	C18—H18A	0.9700
C2—C3	1.343 (6)	C18—H18B	0.9700
C2—H2	0.9300	C19—C20	1.486 (6)
C3—C7	1.508 (5)	C19—H19A	0.9700
C3—C4	1.516 (5)	C19—H19B	0.9700
C4—C10	1.536 (5)	C21—H21A	0.9600
C4—C5	1.544 (5)	C21—H21B	0.9600
C4—C21	1.559 (5)	C21—H21C	0.9600
C5—C6	1.520 (6)	C22—H22A	0.9600
C5—H5A	0.9700	C22—H22B	0.9600
C5—H5B	0.9700	C22—H22C	0.9600
C6—H6A	0.9700	C24—H24A	0.9600
C6—H6B	0.9700	C24—H24B	0.9600
C7—C8	1.525 (5)	C24—H24C	0.9600
C7—H7A	0.9700	O8—C81	1.409 (11)
C7—H7B	0.9700	O8—H8A	0.9668
C8—C23	1.510 (5)	C81—C82	1.494 (11)
C8—C9	1.539 (5)	C81—H81A	0.9700
C8—H8	0.9800	C81—H81B	0.9700
C9—C14	1.519 (5)	C82—H82A	0.9600
C9—C10	1.523 (5)	C82—H82B	0.9600
C9—H9	0.9800	C82—H82C	0.9600
C10—C11	1.482 (5)	O9—C91	1.403 (11)
C11—C12	1.512 (5)	O9—H9A	0.9804
C11—H11	0.9800	C91—C92	1.483 (11)
C12—C13	1.535 (5)	C91—H91A	0.9700
C12—H12A	0.9700	C91—H91B	0.9700
C12—H12B	0.9700	C92—H92A	0.9600
C13—C14	1.544 (5)	C92—H92B	0.9600
C13—C17	1.545 (6)	C92—H92C	0.9600
C13—C22	1.548 (6)

C10—O2—C11	61.2 (2)	C14—C15—H15A	110.7
C20—O3—C17	112.0 (3)	C16—C15—H15B	110.7
C23—O6—C24	117.8 (4)	C14—C15—H15B	110.7
O1—C1—C2	121.9 (5)	H15A—C15—H15B	108.8
O1—C1—C6	120.8 (4)	C17—C16—C15	105.6 (3)
C2—C1—C6	117.3 (4)	C17—C16—H16A	110.6
C3—C2—C1	123.9 (4)	C15—C16—H16A	110.6
C3—C2—H2	118.1	C17—C16—H16B	110.6
C1—C2—H2	118.1	C15—C16—H16B	110.6
C2—C3—C7	118.9 (4)	H16A—C16—H16B	108.7
C2—C3—C4	122.8 (3)	O3—C17—C18	103.4 (3)
C7—C3—C4	118.3 (3)	O3—C17—C16	108.3 (3)
C3—C4—C10	110.1 (3)	C18—C17—C16	113.9 (4)
C3—C4—C5	109.1 (3)	O3—C17—C13	111.0 (3)
C10—C4—C5	111.4 (3)	C18—C17—C13	116.0 (3)
C3—C4—C21	109.4 (3)	C16—C17—C13	104.3 (3)
C10—C4—C21	107.4 (3)	C17—C18—C19	104.4 (3)
C5—C4—C21	109.4 (3)	C17—C18—H18A	110.9
C6—C5—C4	113.6 (3)	C19—C18—H18A	110.9
C6—C5—H5A	108.8	C17—C18—H18B	110.9
C4—C5—H5A	108.8	C19—C18—H18B	110.9
C6—C5—H5B	108.8	H18A—C18—H18B	108.9
C4—C5—H5B	108.8	C20—C19—C18	103.0 (4)
H5A—C5—H5B	107.7	C20—C19—H19A	111.2
C1—C6—C5	112.0 (4)	C18—C19—H19A	111.2
C1—C6—H6A	109.2	C20—C19—H19B	111.2
C5—C6—H6A	109.2	C18—C19—H19B	111.2
C1—C6—H6B	109.2	H19A—C19—H19B	109.1
C5—C6—H6B	109.2	O4—C20—O3	120.5 (4)
H6A—C6—H6B	107.9	O4—C20—C19	128.5 (4)
C3—C7—C8	113.1 (3)	O3—C20—C19	110.9 (3)
C3—C7—H7A	109.0	C4—C21—H21A	109.5
C8—C7—H7A	109.0	C4—C21—H21B	109.5
C3—C7—H7B	109.0	H21A—C21—H21B	109.5
C8—C7—H7B	109.0	C4—C21—H21C	109.5
H7A—C7—H7B	107.8	H21A—C21—H21C	109.5
C23—C8—C7	114.6 (3)	H21B—C21—H21C	109.5
C23—C8—C9	112.0 (3)	C13—C22—H22A	109.5
C7—C8—C9	108.2 (3)	C13—C22—H22B	109.5
C23—C8—H8	107.2	H22A—C22—H22B	109.5
C7—C8—H8	107.2	C13—C22—H22C	109.5
C9—C8—H8	107.2	H22A—C22—H22C	109.5
C14—C9—C10	111.8 (3)	H22B—C22—H22C	109.5
C14—C9—C8	115.3 (3)	O5—C23—O6	122.7 (4)
C10—C9—C8	109.7 (3)	O5—C23—C8	124.9 (4)
C14—C9—H9	106.5	O6—C23—C8	112.4 (3)
C10—C9—H9	106.5	O6—C24—H24A	109.5
C8—C9—H9	106.5	O6—C24—H24B	109.5
O2—C10—C11	59.7 (2)	H24A—C24—H24B	109.5
O2—C10—C9	112.2 (3)	O6—C24—H24C	109.5
C11—C10—C9	118.1 (3)	H24A—C24—H24C	109.5
O2—C10—C4	116.2 (3)	H24B—C24—H24C	109.5
C11—C10—C4	121.5 (3)	C81—O8—H8A	120.4
C9—C10—C4	116.0 (3)	C81—O8—H9A	91.0
O2—C11—C10	59.1 (2)	O8—C81—C82	111.1 (11)
O2—C11—C12	116.5 (3)	O8—C81—H81A	109.4
C10—C11—C12	124.6 (3)	C82—C81—H81A	109.4
O2—C11—H11	114.9	O8—C81—H81B	109.4
C10—C11—H11	114.9	C82—C81—H81B	109.4
C12—C11—H11	114.9	H81A—C81—H81B	108.0
C11—C12—C13	112.3 (3)	C81—C82—H82A	109.5
C11—C12—H12A	109.1	C81—C82—H82B	109.5
C13—C12—H12A	109.1	H82A—C82—H82B	109.5
C11—C12—H12B	109.1	C81—C82—H82C	109.5
C13—C12—H12B	109.1	H82A—C82—H82C	109.5
H12A—C12—H12B	107.9	H82B—C82—H82C	109.5
C12—C13—C14	109.0 (3)	C91—O9—H9A	115.6
C12—C13—C17	117.6 (3)	O9—C91—C92	112.3 (12)
C14—C13—C17	100.0 (3)	O9—C91—H91A	109.1
C12—C13—C22	108.5 (3)	C92—C91—H91A	109.1
C14—C13—C22	111.7 (3)	O9—C91—H91B	109.1
C17—C13—C22	110.0 (3)	C92—C91—H91B	109.1
C9—C14—C13	112.8 (3)	H91A—C91—H91B	107.9
C9—C14—C15	116.6 (3)	C91—C92—H92A	109.5
C13—C14—C15	104.6 (3)	C91—C92—H92B	109.5
C9—C14—H14	107.5	H92A—C92—H92B	109.5
C13—C14—H14	107.5	C91—C92—H92C	109.5
C15—C14—H14	107.5	H92A—C92—H92C	109.5
C16—C15—C14	105.3 (3)	H92B—C92—H92C	109.5
C16—C15—H15A	110.7

O1—C1—C2—C3	177.4 (5)	O2—C11—C12—C13	−81.0 (4)
C6—C1—C2—C3	−2.3 (7)	C10—C11—C12—C13	−11.7 (5)
C1—C2—C3—C7	176.2 (4)	C11—C12—C13—C14	43.1 (4)
C1—C2—C3—C4	−1.5 (7)	C11—C12—C13—C17	155.9 (3)
C2—C3—C4—C10	−143.4 (4)	C11—C12—C13—C22	−78.6 (4)
C7—C3—C4—C10	38.9 (4)	C10—C9—C14—C13	51.8 (4)
C2—C3—C4—C5	−20.9 (5)	C8—C9—C14—C13	178.0 (3)
C7—C3—C4—C5	161.4 (3)	C10—C9—C14—C15	172.9 (3)
C2—C3—C4—C21	98.7 (4)	C8—C9—C14—C15	−60.9 (5)
C7—C3—C4—C21	−79.0 (4)	C12—C13—C14—C9	−66.2 (4)
C3—C4—C5—C6	47.3 (5)	C17—C13—C14—C9	169.9 (3)
C10—C4—C5—C6	169.0 (4)	C22—C13—C14—C9	53.7 (4)
C21—C4—C5—C6	−72.4 (5)	C12—C13—C14—C15	166.1 (3)
O1—C1—C6—C5	−150.7 (5)	C17—C13—C14—C15	42.2 (4)
C2—C1—C6—C5	29.0 (7)	C22—C13—C14—C15	−74.1 (4)
C4—C5—C6—C1	−52.5 (6)	C9—C14—C15—C16	−151.0 (4)
C2—C3—C7—C8	134.9 (4)	C13—C14—C15—C16	−25.7 (5)
C4—C3—C7—C8	−47.3 (5)	C14—C15—C16—C17	−1.4 (5)
C3—C7—C8—C23	−70.2 (4)	C20—O3—C17—C18	14.6 (5)
C3—C7—C8—C9	55.7 (4)	C20—O3—C17—C16	135.7 (4)
C23—C8—C9—C14	−59.7 (4)	C20—O3—C17—C13	−110.5 (4)
C7—C8—C9—C14	172.9 (3)	C15—C16—C17—O3	146.3 (4)
C23—C8—C9—C10	67.5 (4)	C15—C16—C17—C18	−99.4 (4)
C7—C8—C9—C10	−59.9 (4)	C15—C16—C17—C13	28.0 (5)
C11—O2—C10—C9	−110.5 (3)	C12—C13—C17—O3	82.8 (4)
C11—O2—C10—C4	112.7 (4)	C14—C13—C17—O3	−159.5 (3)
C14—C9—C10—O2	48.9 (4)	C22—C13—C17—O3	−41.9 (4)
C8—C9—C10—O2	−80.2 (4)	C12—C13—C17—C18	−34.7 (5)
C14—C9—C10—C11	−17.5 (5)	C14—C13—C17—C18	83.0 (4)
C8—C9—C10—C11	−146.7 (3)	C22—C13—C17—C18	−159.5 (3)
C14—C9—C10—C4	−174.2 (3)	C12—C13—C17—C16	−160.8 (3)
C8—C9—C10—C4	56.6 (4)	C14—C13—C17—C16	−43.1 (4)
C3—C4—C10—O2	91.2 (4)	C22—C13—C17—C16	74.5 (4)
C5—C4—C10—O2	−30.0 (5)	O3—C17—C18—C19	−23.4 (4)
C21—C4—C10—O2	−149.7 (3)	C16—C17—C18—C19	−140.6 (4)
C3—C4—C10—C11	160.2 (3)	C13—C17—C18—C19	98.3 (4)
C5—C4—C10—C11	39.1 (5)	C17—C18—C19—C20	23.9 (5)
C21—C4—C10—C11	−80.7 (4)	C17—O3—C20—O4	178.1 (4)
C3—C4—C10—C9	−44.0 (4)	C17—O3—C20—C19	1.0 (5)
C5—C4—C10—C9	−165.1 (3)	C18—C19—C20—O4	167.2 (5)
C21—C4—C10—C9	75.1 (4)	C18—C19—C20—O3	−16.1 (5)
C10—O2—C11—C12	116.1 (3)	C24—O6—C23—O5	−2.4 (6)
C9—C10—C11—O2	100.7 (3)	C24—O6—C23—C8	177.9 (4)
C4—C10—C11—O2	−104.0 (3)	C7—C8—C23—O5	−164.2 (4)
O2—C10—C11—C12	−102.7 (4)	C9—C8—C23—O5	72.0 (5)
C9—C10—C11—C12	−2.0 (5)	C7—C8—C23—O6	15.5 (4)
C4—C10—C11—C12	153.4 (3)	C9—C8—C23—O6	−108.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8A···O1ⁱ	0.96	2.19	3.15 (4)	178
O9—H9A···O1ⁱ	0.98	2.34	3.32 (4)	177
C6—H6A···O2ⁱⁱ	0.97	2.53	3.447 (6)	157
C7—H7B···O5ⁱⁱⁱ	0.97	2.52	3.467 (5)	164
C11—H11···O4^iv	0.98	2.57	3.337 (5)	135
C14—H14···O5	0.98	2.50	3.103 (5)	120
C21—H21A···O5ⁱⁱⁱ	0.96	2.46	3.351 (6)	154
C92—H92A···O1^v	0.96	2.54	3.44 (6)	155

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

Experimental details

Crystal data
Chemical formula	C₂₄H₃₀O₆·C₂H₆O
M_r	460.55
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	295
a, b, c (Å)	8.3236 (5), 12.8306 (9), 23.3173 (13)
V (Å³)	2490.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.16 × 0.14

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19548, 2559, 1955
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.151, 1.05
No. of reflections	2559
No. of parameters	293
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.19

Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2002), SIR92 (Altomare et al., 1993), SHELXL97 (Sheldrick, 2008), 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
O8—H8A···O1ⁱ	0.96	2.19	3.15 (4)	178
O9—H9A···O1ⁱ	0.98	2.34	3.32 (4)	177

Symmetry code: (i) x+1/2, −y+3/2, −z.

Acknowledgements

The work was supported by the ZIJIN project of Zhejiang University, China.

References

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