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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536808009240/ng2439sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536808009240/ng2439Isup2.hkl
Contains datablock I

CCDC reference: 653034

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.005 Å
  • Disorder in solvent or counterion
  • R factor = 0.056
  • wR factor = 0.152
  • Data-to-parameter ratio = 8.7

checkCIF/PLATON results

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Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C23 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5 PLAT432_ALERT_2_C Short Inter X...Y Contact O4 .. C24 .. 3.00 Ang.
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 25.20 From the CIF: _reflns_number_total 2559 Count of symmetry unique reflns 2564 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 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 ....... 6
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 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 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 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

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.

Refinement top

The lattice ethanol molecule is disordered in the crystal structure; a two-site model with each 0.5 site occupancies was adopted in the refinement. The C—C and C—O distances for the disordered solvent molecule were constrained to 1.50±0.01 and 1.40±0.01 Å, respectively; atomic displacement parameters for non-H atoms of the disordered solvent molecule were constrained to be the same. Hydroxyl H atoms were placed in chemical sensible positions and refined in riding mode with Uiso(H) = 1.5Ueq(O). Other H atoms were placed in calculated positions with C—H = 0.93 to 0.98 Å, and refined in riding mode with Uiso(H) = 1.5Ueq(C) for methyl or 1.2Ueq(C) for others. In the absence of significant anomalous scattering effects, Friedel pairs were merged; the absolute configuration was not determined.

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
[Figure 1] 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·C2H6OF(000) = 992
Mr = 460.55Dx = 1.228 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 4788 reflections
a = 8.3236 (5) Åθ = 3.2–25.2°
b = 12.8306 (9) ŵ = 0.09 mm1
c = 23.3173 (13) ÅT = 295 K
V = 2490.2 (3) Å3Prism, colorless
Z = 40.20 × 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 tubeRint = 0.054
Graphite monochromatorθmax = 25.2°, θmin = 3.0°
ω scansh = 98
19548 measured reflectionsk = 1515
2559 independent reflectionsl = 2727
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.151H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.0933P)2 + 0.2684P]
where P = (Fo2 + 2Fc2)/3
2559 reflections(Δ/σ)max = 0.002
293 parametersΔρmax = 0.30 e Å3
6 restraintsΔρmin = 0.19 e Å3
Crystal data top
C24H30O6·C2H6OV = 2490.2 (3) Å3
Mr = 460.55Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 8.3236 (5) ŵ = 0.09 mm1
b = 12.8306 (9) ÅT = 295 K
c = 23.3173 (13) Å0.20 × 0.16 × 0.14 mm
Data collection top
Rigaku R-AXIS RAPID IP
diffractometer
1955 reflections with I > 2σ(I)
19548 measured reflectionsRint = 0.054
2559 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0566 restraints
wR(F2) = 0.151H-atom parameters constrained
S = 1.05Δρmax = 0.30 e Å3
2559 reflectionsΔρmin = 0.19 e Å3
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
xyzUiso*/UeqOcc. (<1)
O10.0903 (5)0.5823 (4)0.10016 (17)0.1137 (15)
O20.1457 (3)0.82438 (19)0.29175 (10)0.0474 (6)
O30.4884 (4)0.8328 (2)0.49749 (10)0.0644 (8)
O40.3946 (5)0.8951 (3)0.57892 (12)0.0842 (10)
O50.4856 (5)0.9197 (3)0.22555 (13)0.0866 (11)
O60.3136 (4)0.8354 (2)0.17081 (12)0.0691 (8)
C10.0244 (6)0.5948 (4)0.1464 (2)0.0742 (13)
C20.1457 (6)0.6130 (3)0.15092 (19)0.0642 (11)
H20.20620.61220.11740.077*
C30.2222 (5)0.6310 (3)0.20064 (16)0.0476 (9)
C40.1357 (4)0.6367 (3)0.25779 (16)0.0481 (9)
C50.0438 (4)0.6600 (4)0.2471 (2)0.0653 (11)
H5A0.10240.64990.28260.078*
H5B0.05520.73260.23610.078*
C60.1187 (6)0.5921 (4)0.2008 (2)0.0759 (13)
H6A0.12490.52080.21450.091*
H6B0.22720.61600.19330.091*
C70.4024 (4)0.6423 (3)0.20023 (16)0.0515 (9)
H7A0.43850.65120.16100.062*
H7B0.45020.57870.21490.062*
C80.4618 (4)0.7341 (3)0.23596 (14)0.0465 (9)
H80.57900.72850.23830.056*
C90.3961 (4)0.7217 (3)0.29729 (14)0.0432 (8)
H90.42990.65260.31050.052*
C100.2131 (4)0.7204 (3)0.29597 (15)0.0438 (8)
C110.1258 (4)0.7665 (3)0.34520 (16)0.0467 (9)
H110.01780.73840.35160.056*
C120.2055 (4)0.8119 (3)0.39783 (15)0.0508 (9)
H12A0.15250.78520.43180.061*
H12B0.19250.88710.39750.061*
C130.3852 (5)0.7856 (3)0.40082 (14)0.0474 (9)
C140.4600 (4)0.7996 (3)0.34071 (14)0.0451 (9)
H140.43090.86940.32710.054*
C150.6431 (5)0.7989 (4)0.35129 (17)0.0646 (12)
H15A0.68650.72930.34630.078*
H15B0.69720.84580.32500.078*
C160.6647 (5)0.8359 (5)0.41383 (17)0.0721 (13)
H16A0.71530.78200.43680.086*
H16B0.73070.89810.41530.086*
C170.4943 (5)0.8590 (3)0.43599 (14)0.0534 (10)
C180.4499 (5)0.9740 (3)0.43479 (17)0.0578 (10)
H18A0.38430.99000.40150.069*
H18B0.54551.01730.43390.069*
C190.3553 (7)0.9913 (4)0.49035 (16)0.0727 (13)
H19A0.37891.05900.50690.087*
H19B0.24060.98580.48370.087*
C200.4135 (6)0.9058 (3)0.52799 (16)0.0629 (11)
C210.1522 (6)0.5303 (3)0.28953 (19)0.0659 (11)
H21A0.26390.51440.29490.099*
H21B0.10270.47650.26710.099*
H21C0.10020.53460.32620.099*
C220.4032 (6)0.6722 (3)0.42265 (17)0.0648 (11)
H22A0.36980.66840.46200.097*
H22B0.51350.65110.41960.097*
H22C0.33740.62680.39990.097*
C230.4237 (5)0.8399 (3)0.21110 (15)0.0503 (9)
C240.2627 (8)0.9320 (4)0.1450 (2)0.0944 (18)
H24A0.26700.98670.17310.142*
H24B0.15460.92490.13120.142*
H24C0.33260.94890.11360.142*
O80.547 (6)0.823 (3)0.0144 (17)0.431 (13)*0.50
H8A0.50240.85270.02010.646*0.50
C810.715 (6)0.815 (6)0.021 (2)0.431 (13)*0.50
H81A0.76820.84680.01140.517*0.50
H81B0.74550.74230.02270.517*0.50
C820.769 (7)0.868 (5)0.075 (2)0.431 (13)*0.50
H82A0.81880.81810.10000.646*0.50
H82B0.67780.89830.09400.646*0.50
H82C0.84470.92190.06570.646*0.50
O90.632 (5)0.917 (4)0.0182 (15)0.431 (13)*0.50
H9A0.56500.91950.01630.646*0.50
C910.625 (7)0.824 (4)0.050 (3)0.431 (13)*0.50
H91A0.65190.76600.02490.517*0.50
H91B0.51550.81360.06320.517*0.50
C920.735 (7)0.825 (5)0.100 (2)0.431 (13)*0.50
H92A0.76140.75410.11000.646*0.50
H92B0.68390.85840.13150.646*0.50
H92C0.83160.86140.08980.646*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.100 (3)0.143 (4)0.098 (3)0.039 (3)0.033 (2)0.015 (3)
O20.0473 (14)0.0399 (13)0.0551 (13)0.0060 (11)0.0018 (12)0.0004 (11)
O30.091 (2)0.0635 (17)0.0388 (13)0.0233 (17)0.0092 (14)0.0007 (13)
O40.127 (3)0.079 (2)0.0468 (16)0.021 (2)0.0019 (18)0.0003 (15)
O50.114 (3)0.072 (2)0.0730 (19)0.039 (2)0.005 (2)0.0047 (17)
O60.087 (2)0.0521 (17)0.0681 (16)0.0022 (17)0.0233 (16)0.0092 (14)
C10.070 (3)0.068 (3)0.084 (3)0.016 (2)0.015 (3)0.018 (3)
C20.070 (3)0.062 (3)0.061 (2)0.006 (2)0.003 (2)0.011 (2)
C30.053 (2)0.0314 (18)0.058 (2)0.0005 (16)0.0028 (19)0.0040 (16)
C40.0421 (18)0.041 (2)0.062 (2)0.0008 (16)0.0030 (18)0.0031 (16)
C50.045 (2)0.060 (3)0.091 (3)0.001 (2)0.001 (2)0.023 (2)
C60.053 (2)0.063 (3)0.112 (4)0.009 (2)0.008 (3)0.023 (3)
C70.052 (2)0.054 (2)0.0484 (19)0.0091 (18)0.0050 (18)0.0047 (18)
C80.0345 (18)0.061 (2)0.0443 (19)0.0012 (17)0.0017 (16)0.0036 (17)
C90.0380 (17)0.047 (2)0.0443 (17)0.0067 (15)0.0050 (16)0.0000 (16)
C100.0453 (18)0.0397 (19)0.0464 (18)0.0024 (16)0.0052 (17)0.0026 (16)
C110.0408 (19)0.042 (2)0.057 (2)0.0010 (16)0.0100 (17)0.0014 (17)
C120.054 (2)0.052 (2)0.0461 (18)0.0068 (19)0.0109 (18)0.0004 (17)
C130.052 (2)0.052 (2)0.0380 (17)0.0077 (17)0.0021 (17)0.0009 (16)
C140.0380 (18)0.058 (2)0.0397 (17)0.0012 (17)0.0022 (15)0.0004 (16)
C150.045 (2)0.095 (4)0.054 (2)0.007 (2)0.0038 (19)0.012 (2)
C160.053 (2)0.103 (4)0.060 (2)0.017 (3)0.010 (2)0.016 (3)
C170.063 (2)0.060 (2)0.0365 (17)0.008 (2)0.0021 (17)0.0003 (17)
C180.066 (3)0.056 (2)0.051 (2)0.001 (2)0.0043 (19)0.0061 (19)
C190.105 (4)0.061 (3)0.052 (2)0.016 (3)0.004 (2)0.000 (2)
C200.086 (3)0.059 (3)0.043 (2)0.010 (2)0.005 (2)0.0002 (19)
C210.071 (3)0.048 (2)0.079 (3)0.001 (2)0.014 (2)0.005 (2)
C220.088 (3)0.056 (2)0.051 (2)0.017 (2)0.004 (2)0.0080 (19)
C230.053 (2)0.055 (2)0.0424 (18)0.0129 (19)0.0082 (17)0.0015 (17)
C240.122 (5)0.071 (3)0.090 (3)0.020 (3)0.018 (3)0.018 (3)
Geometric parameters (Å, º) top
O1—C11.221 (6)C14—C151.545 (5)
O2—C101.451 (4)C14—H140.9800
O2—C111.460 (4)C15—C161.544 (6)
O3—C201.331 (5)C15—H15A0.9700
O3—C171.474 (4)C15—H15B0.9700
O4—C201.206 (5)C16—C171.538 (6)
O5—C231.195 (5)C16—H16A0.9700
O6—C231.314 (5)C16—H16B0.9700
O6—C241.441 (5)C17—C181.522 (6)
C1—C21.438 (7)C18—C191.532 (6)
C1—C61.492 (7)C18—H18A0.9700
C2—C31.343 (6)C18—H18B0.9700
C2—H20.9300C19—C201.486 (6)
C3—C71.508 (5)C19—H19A0.9700
C3—C41.516 (5)C19—H19B0.9700
C4—C101.536 (5)C21—H21A0.9600
C4—C51.544 (5)C21—H21B0.9600
C4—C211.559 (5)C21—H21C0.9600
C5—C61.520 (6)C22—H22A0.9600
C5—H5A0.9700C22—H22B0.9600
C5—H5B0.9700C22—H22C0.9600
C6—H6A0.9700C24—H24A0.9600
C6—H6B0.9700C24—H24B0.9600
C7—C81.525 (5)C24—H24C0.9600
C7—H7A0.9700O8—C811.409 (11)
C7—H7B0.9700O8—H8A0.9668
C8—C231.510 (5)C81—C821.494 (11)
C8—C91.539 (5)C81—H81A0.9700
C8—H80.9800C81—H81B0.9700
C9—C141.519 (5)C82—H82A0.9600
C9—C101.523 (5)C82—H82B0.9600
C9—H90.9800C82—H82C0.9600
C10—C111.482 (5)O9—C911.403 (11)
C11—C121.512 (5)O9—H9A0.9804
C11—H110.9800C91—C921.483 (11)
C12—C131.535 (5)C91—H91A0.9700
C12—H12A0.9700C91—H91B0.9700
C12—H12B0.9700C92—H92A0.9600
C13—C141.544 (5)C92—H92B0.9600
C13—C171.545 (6)C92—H92C0.9600
C13—C221.548 (6)
C10—O2—C1161.2 (2)C14—C15—H15A110.7
C20—O3—C17112.0 (3)C16—C15—H15B110.7
C23—O6—C24117.8 (4)C14—C15—H15B110.7
O1—C1—C2121.9 (5)H15A—C15—H15B108.8
O1—C1—C6120.8 (4)C17—C16—C15105.6 (3)
C2—C1—C6117.3 (4)C17—C16—H16A110.6
C3—C2—C1123.9 (4)C15—C16—H16A110.6
C3—C2—H2118.1C17—C16—H16B110.6
C1—C2—H2118.1C15—C16—H16B110.6
C2—C3—C7118.9 (4)H16A—C16—H16B108.7
C2—C3—C4122.8 (3)O3—C17—C18103.4 (3)
C7—C3—C4118.3 (3)O3—C17—C16108.3 (3)
C3—C4—C10110.1 (3)C18—C17—C16113.9 (4)
C3—C4—C5109.1 (3)O3—C17—C13111.0 (3)
C10—C4—C5111.4 (3)C18—C17—C13116.0 (3)
C3—C4—C21109.4 (3)C16—C17—C13104.3 (3)
C10—C4—C21107.4 (3)C17—C18—C19104.4 (3)
C5—C4—C21109.4 (3)C17—C18—H18A110.9
C6—C5—C4113.6 (3)C19—C18—H18A110.9
C6—C5—H5A108.8C17—C18—H18B110.9
C4—C5—H5A108.8C19—C18—H18B110.9
C6—C5—H5B108.8H18A—C18—H18B108.9
C4—C5—H5B108.8C20—C19—C18103.0 (4)
H5A—C5—H5B107.7C20—C19—H19A111.2
C1—C6—C5112.0 (4)C18—C19—H19A111.2
C1—C6—H6A109.2C20—C19—H19B111.2
C5—C6—H6A109.2C18—C19—H19B111.2
C1—C6—H6B109.2H19A—C19—H19B109.1
C5—C6—H6B109.2O4—C20—O3120.5 (4)
H6A—C6—H6B107.9O4—C20—C19128.5 (4)
C3—C7—C8113.1 (3)O3—C20—C19110.9 (3)
C3—C7—H7A109.0C4—C21—H21A109.5
C8—C7—H7A109.0C4—C21—H21B109.5
C3—C7—H7B109.0H21A—C21—H21B109.5
C8—C7—H7B109.0C4—C21—H21C109.5
H7A—C7—H7B107.8H21A—C21—H21C109.5
C23—C8—C7114.6 (3)H21B—C21—H21C109.5
C23—C8—C9112.0 (3)C13—C22—H22A109.5
C7—C8—C9108.2 (3)C13—C22—H22B109.5
C23—C8—H8107.2H22A—C22—H22B109.5
C7—C8—H8107.2C13—C22—H22C109.5
C9—C8—H8107.2H22A—C22—H22C109.5
C14—C9—C10111.8 (3)H22B—C22—H22C109.5
C14—C9—C8115.3 (3)O5—C23—O6122.7 (4)
C10—C9—C8109.7 (3)O5—C23—C8124.9 (4)
C14—C9—H9106.5O6—C23—C8112.4 (3)
C10—C9—H9106.5O6—C24—H24A109.5
C8—C9—H9106.5O6—C24—H24B109.5
O2—C10—C1159.7 (2)H24A—C24—H24B109.5
O2—C10—C9112.2 (3)O6—C24—H24C109.5
C11—C10—C9118.1 (3)H24A—C24—H24C109.5
O2—C10—C4116.2 (3)H24B—C24—H24C109.5
C11—C10—C4121.5 (3)C81—O8—H8A120.4
C9—C10—C4116.0 (3)C81—O8—H9A91.0
O2—C11—C1059.1 (2)O8—C81—C82111.1 (11)
O2—C11—C12116.5 (3)O8—C81—H81A109.4
C10—C11—C12124.6 (3)C82—C81—H81A109.4
O2—C11—H11114.9O8—C81—H81B109.4
C10—C11—H11114.9C82—C81—H81B109.4
C12—C11—H11114.9H81A—C81—H81B108.0
C11—C12—C13112.3 (3)C81—C82—H82A109.5
C11—C12—H12A109.1C81—C82—H82B109.5
C13—C12—H12A109.1H82A—C82—H82B109.5
C11—C12—H12B109.1C81—C82—H82C109.5
C13—C12—H12B109.1H82A—C82—H82C109.5
H12A—C12—H12B107.9H82B—C82—H82C109.5
C12—C13—C14109.0 (3)C91—O9—H9A115.6
C12—C13—C17117.6 (3)O9—C91—C92112.3 (12)
C14—C13—C17100.0 (3)O9—C91—H91A109.1
C12—C13—C22108.5 (3)C92—C91—H91A109.1
C14—C13—C22111.7 (3)O9—C91—H91B109.1
C17—C13—C22110.0 (3)C92—C91—H91B109.1
C9—C14—C13112.8 (3)H91A—C91—H91B107.9
C9—C14—C15116.6 (3)C91—C92—H92A109.5
C13—C14—C15104.6 (3)C91—C92—H92B109.5
C9—C14—H14107.5H92A—C92—H92B109.5
C13—C14—H14107.5C91—C92—H92C109.5
C15—C14—H14107.5H92A—C92—H92C109.5
C16—C15—C14105.3 (3)H92B—C92—H92C109.5
C16—C15—H15A110.7
O1—C1—C2—C3177.4 (5)O2—C11—C12—C1381.0 (4)
C6—C1—C2—C32.3 (7)C10—C11—C12—C1311.7 (5)
C1—C2—C3—C7176.2 (4)C11—C12—C13—C1443.1 (4)
C1—C2—C3—C41.5 (7)C11—C12—C13—C17155.9 (3)
C2—C3—C4—C10143.4 (4)C11—C12—C13—C2278.6 (4)
C7—C3—C4—C1038.9 (4)C10—C9—C14—C1351.8 (4)
C2—C3—C4—C520.9 (5)C8—C9—C14—C13178.0 (3)
C7—C3—C4—C5161.4 (3)C10—C9—C14—C15172.9 (3)
C2—C3—C4—C2198.7 (4)C8—C9—C14—C1560.9 (5)
C7—C3—C4—C2179.0 (4)C12—C13—C14—C966.2 (4)
C3—C4—C5—C647.3 (5)C17—C13—C14—C9169.9 (3)
C10—C4—C5—C6169.0 (4)C22—C13—C14—C953.7 (4)
C21—C4—C5—C672.4 (5)C12—C13—C14—C15166.1 (3)
O1—C1—C6—C5150.7 (5)C17—C13—C14—C1542.2 (4)
C2—C1—C6—C529.0 (7)C22—C13—C14—C1574.1 (4)
C4—C5—C6—C152.5 (6)C9—C14—C15—C16151.0 (4)
C2—C3—C7—C8134.9 (4)C13—C14—C15—C1625.7 (5)
C4—C3—C7—C847.3 (5)C14—C15—C16—C171.4 (5)
C3—C7—C8—C2370.2 (4)C20—O3—C17—C1814.6 (5)
C3—C7—C8—C955.7 (4)C20—O3—C17—C16135.7 (4)
C23—C8—C9—C1459.7 (4)C20—O3—C17—C13110.5 (4)
C7—C8—C9—C14172.9 (3)C15—C16—C17—O3146.3 (4)
C23—C8—C9—C1067.5 (4)C15—C16—C17—C1899.4 (4)
C7—C8—C9—C1059.9 (4)C15—C16—C17—C1328.0 (5)
C11—O2—C10—C9110.5 (3)C12—C13—C17—O382.8 (4)
C11—O2—C10—C4112.7 (4)C14—C13—C17—O3159.5 (3)
C14—C9—C10—O248.9 (4)C22—C13—C17—O341.9 (4)
C8—C9—C10—O280.2 (4)C12—C13—C17—C1834.7 (5)
C14—C9—C10—C1117.5 (5)C14—C13—C17—C1883.0 (4)
C8—C9—C10—C11146.7 (3)C22—C13—C17—C18159.5 (3)
C14—C9—C10—C4174.2 (3)C12—C13—C17—C16160.8 (3)
C8—C9—C10—C456.6 (4)C14—C13—C17—C1643.1 (4)
C3—C4—C10—O291.2 (4)C22—C13—C17—C1674.5 (4)
C5—C4—C10—O230.0 (5)O3—C17—C18—C1923.4 (4)
C21—C4—C10—O2149.7 (3)C16—C17—C18—C19140.6 (4)
C3—C4—C10—C11160.2 (3)C13—C17—C18—C1998.3 (4)
C5—C4—C10—C1139.1 (5)C17—C18—C19—C2023.9 (5)
C21—C4—C10—C1180.7 (4)C17—O3—C20—O4178.1 (4)
C3—C4—C10—C944.0 (4)C17—O3—C20—C191.0 (5)
C5—C4—C10—C9165.1 (3)C18—C19—C20—O4167.2 (5)
C21—C4—C10—C975.1 (4)C18—C19—C20—O316.1 (5)
C10—O2—C11—C12116.1 (3)C24—O6—C23—O52.4 (6)
C9—C10—C11—O2100.7 (3)C24—O6—C23—C8177.9 (4)
C4—C10—C11—O2104.0 (3)C7—C8—C23—O5164.2 (4)
O2—C10—C11—C12102.7 (4)C9—C8—C23—O572.0 (5)
C9—C10—C11—C122.0 (5)C7—C8—C23—O615.5 (4)
C4—C10—C11—C12153.4 (3)C9—C8—C23—O6108.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O8—H8A···O1i0.962.193.15 (4)178
O9—H9A···O1i0.982.343.32 (4)177
C6—H6A···O2ii0.972.533.447 (6)157
C7—H7B···O5iii0.972.523.467 (5)164
C11—H11···O4iv0.982.573.337 (5)135
C14—H14···O50.982.503.103 (5)120
C21—H21A···O5iii0.962.463.351 (6)154
C92—H92A···O1v0.962.543.44 (6)155
Symmetry codes: (i) x+1/2, y+3/2, z; (ii) x, y1/2, z+1/2; (iii) x+1, y1/2, z+1/2; (iv) x1/2, y+3/2, z+1; (v) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC24H30O6·C2H6O
Mr460.55
Crystal system, space groupOrthorhombic, P212121
Temperature (K)295
a, b, c (Å)8.3236 (5), 12.8306 (9), 23.3173 (13)
V3)2490.2 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.20 × 0.16 × 0.14
Data collection
DiffractometerRigaku R-AXIS RAPID IP
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
19548, 2559, 1955
Rint0.054
(sin θ/λ)max1)0.599
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.151, 1.05
No. of reflections2559
No. of parameters293
No. of restraints6
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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···AD—HH···AD···AD—H···A
O8—H8A···O1i0.962.193.15 (4)178
O9—H9A···O1i0.982.343.32 (4)177
Symmetry code: (i) x+1/2, y+3/2, z.
 

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