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Acta Crystallogr Sect E Struct Rep Online. 2008 May 1; 64(Pt 5): o829.
Published online 2008 April 10. doi:  10.1107/S1600536808009240
PMCID: PMC2961083

Eplerenone ethanol solvate

Abstract

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 [triangle]). For related structures, see: Grob et al. (1997 [triangle]); Yang et al. (2007 [triangle]); Xu et al. (2007 [triangle]). For ring analysis, see: Spek (2003 [triangle]).

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Object name is e-64-0o829-scheme1.jpg

Experimental

Crystal data

  • C24H30O6·C2H6O
  • M r = 460.55
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o829-efi1.jpg
  • 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[F 2 > 2σ(F 2)] = 0.056
  • wR(F 2) = 0.151
  • S = 1.05
  • 2559 reflections
  • 293 parameters
  • 6 restraints
  • H-atom parameters constrained
  • Δρmax = 0.30 e Å−3
  • Δρmin = −0.18 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 [triangle]); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 [triangle]); program(s) used to solve structure: SIR92 (Altomare et al., 1993 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]); software used to prepare material for publication: WinGX (Farrugia, 1999 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

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

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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.

Crystal data

C24H30O6·C2H6OF000 = 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 = 3.2–25.2º
b = 12.8306 (9) ŵ = 0.09 mm1
c = 23.3173 (13) ÅT = 295 (2) K
V = 2490.2 (3) Å3Prism, colorless
Z = 40.20 × 0.16 × 0.14 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer1955 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.054
Monochromator: graphiteθmax = 25.2º
T = 295(2) Kθmin = 3.0º
ω scansh = −9→8
Absorption correction: nonek = −15→15
19548 measured reflectionsl = −27→27
2559 independent reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H-atom parameters constrained
wR(F2) = 0.151  w = 1/[σ2(Fo2) + (0.0933P)2 + 0.2684P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.002
2559 reflectionsΔρmax = 0.30 e Å3
293 parametersΔρmin = −0.18 e Å3
6 restraintsExtinction correction: none
Primary atom site location: structure-invariant direct methods

Special details

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)

xyzUiso*/UeqOcc. (<1)
O1−0.0903 (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)
C1−0.0244 (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)
C5−0.0438 (4)0.6600 (4)0.2471 (2)0.0653 (11)
H5A−0.10240.64990.28260.078*
H5B−0.05520.73260.23610.078*
C6−0.1187 (6)0.5921 (4)0.2008 (2)0.0759 (13)
H6A−0.12490.52080.21450.091*
H6B−0.22720.61600.19330.091*
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
H8A0.50240.8527−0.02010.646*0.50
C810.715 (6)0.815 (6)0.021 (2)0.431 (13)*0.50
H81A0.76820.8468−0.01140.517*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
H9A0.56500.9195−0.01630.646*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)

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, °)

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—C13−81.0 (4)
C6—C1—C2—C3−2.3 (7)C10—C11—C12—C13−11.7 (5)
C1—C2—C3—C7176.2 (4)C11—C12—C13—C1443.1 (4)
C1—C2—C3—C4−1.5 (7)C11—C12—C13—C17155.9 (3)
C2—C3—C4—C10−143.4 (4)C11—C12—C13—C22−78.6 (4)
C7—C3—C4—C1038.9 (4)C10—C9—C14—C1351.8 (4)
C2—C3—C4—C5−20.9 (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—C15−60.9 (5)
C7—C3—C4—C21−79.0 (4)C12—C13—C14—C9−66.2 (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—C6−72.4 (5)C12—C13—C14—C15166.1 (3)
O1—C1—C6—C5−150.7 (5)C17—C13—C14—C1542.2 (4)
C2—C1—C6—C529.0 (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—C8134.9 (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—C1814.6 (5)
C3—C7—C8—C955.7 (4)C20—O3—C17—C16135.7 (4)
C23—C8—C9—C14−59.7 (4)C20—O3—C17—C13−110.5 (4)
C7—C8—C9—C14172.9 (3)C15—C16—C17—O3146.3 (4)
C23—C8—C9—C1067.5 (4)C15—C16—C17—C18−99.4 (4)
C7—C8—C9—C10−59.9 (4)C15—C16—C17—C1328.0 (5)
C11—O2—C10—C9−110.5 (3)C12—C13—C17—O382.8 (4)
C11—O2—C10—C4112.7 (4)C14—C13—C17—O3−159.5 (3)
C14—C9—C10—O248.9 (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—C1883.0 (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—C456.6 (4)C14—C13—C17—C16−43.1 (4)
C3—C4—C10—O291.2 (4)C22—C13—C17—C1674.5 (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—C11160.2 (3)C13—C17—C18—C1998.3 (4)
C5—C4—C10—C1139.1 (5)C17—C18—C19—C2023.9 (5)
C21—C4—C10—C11−80.7 (4)C17—O3—C20—O4178.1 (4)
C3—C4—C10—C9−44.0 (4)C17—O3—C20—C191.0 (5)
C5—C4—C10—C9−165.1 (3)C18—C19—C20—O4167.2 (5)
C21—C4—C10—C975.1 (4)C18—C19—C20—O3−16.1 (5)
C10—O2—C11—C12116.1 (3)C24—O6—C23—O5−2.4 (6)
C9—C10—C11—O2100.7 (3)C24—O6—C23—C8177.9 (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—O572.0 (5)
C9—C10—C11—C12−2.0 (5)C7—C8—C23—O615.5 (4)
C4—C10—C11—C12153.4 (3)C9—C8—C23—O6−108.3 (3)

Hydrogen-bond geometry (Å, °)

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, 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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: NG2439).

References

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