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Acta Crystallogr Sect E Struct Rep Online. 2010 June 1; 66(Pt 6): o1331.
Published online 2010 May 12. doi:  10.1107/S160053681001648X
PMCID: PMC2979527

21-(3-Carboxy­propano­yl)-11β,17-dihydroxy­pregn-4-ene-3,20-dione monohydrate

Abstract

In the title compound, C25H34O8·H2O, the two crylohexane rings adopt chair conformations. In the crystal, the organic mol­ecule and the water mol­ecule are linked by O—H(...)O hydrogen bonds, generating a three-dimensional network.

Related literature

For background to glucocorticoids, see: Schäcke et al. (2002 [triangle]). For the synthesis, see: Fang et al. (2007 [triangle]).

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Object name is e-66-o1331-scheme1.jpg

Experimental

Crystal data

  • C25H34O8·H2O
  • M r = 480.54
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1331-efi1.jpg
  • a = 7.2672 (15) Å
  • b = 16.606 (3) Å
  • c = 20.009 (4) Å
  • V = 2414.7 (8) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.16 × 0.14 × 0.13 mm

Data collection

  • Rigaku R-AXIS RAPID IP diffractometer
  • 21231 measured reflections
  • 2848 independent reflections
  • 2562 reflections with I > 2σ(I)
  • R int = 0.051

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.106
  • S = 1.06
  • 2848 reflections
  • 309 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.17 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 [triangle]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681001648X/hb5414sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001648X/hb5414Isup2.hkl

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

Acknowledgments

The authors thank Dr Yi-Ying Gao (Institute of Process Engineering, Chinese Academy of Science, Beijing) for the structure analysis.

supplementary crystallographic information

Comment

Glucocorticoids (GCs) process varied biological properties such as anti-inflammatory, immunosuppressive and countershock activities (Schäcke et al., 2002). In view of these importances and to determine the molecular conformation, a crystallographic study of the title compound has been carried out.

The molecular structure is shown in Fig. 1. All the bond lengths and angles are within normal ranges. The molecule contains three six-membered rings (A ring atoms C1-C5/C18; B ring atoms C5-C8/C17/C18; C ring atoms C8/C9/C13/C15-C17) and a five-member ring (D ring atoms C9-C13). Ring B and C adopt chair conformations.

In the crystal structure, the molecules are linked via intermolecular O2—H2···O8, O7—H7···O1 interactions. The molecules and water are additionally linked by strong O3—H3A···O9, O9—H2W···O2, O9—H1W···O1 actions (Fig. 2).

Experimental

To a solution of hydrocortisone (5.43 g, 15 mmol) in pyridine (75 ml), succinic anhydride (3 g, 30 mmol) was added dropwise with stirring at room temperature. The mixture was refluxed for 8 hrs. After pouring the solution to ice water (100 ml) and adjusting pH to 5.0-5.5 with 5% HCl (aq), the resulting white solid was obtained and then collected by filtration, washed with water and dried (Fang et al., 2007). Colourless prisms of (I) were recrystalized from ethanol by the slow evaporation of the solvent at room temperature after several days, presumably the water of crystallisation was absorbed from the atmosphere.

Refinement

Anomalous dispersion was negliglble and Friedel pairs were merged before refinement. H atoms of water molecule were located in a difference Fourier map and then refined in riding mode with Uiso(H)=1.5Ueq(O).All the other H atoms were placed in idealized locations as riding atoms, with Uiso(H) = 1.2Ueq(C) for methylene, Uiso(H) = 1.5Ueq(C) for methyl groups and Uiso(H) = 1.5Ueq(O) for hydroxyl groups.

Figures

Fig. 1.
Crystal structure of (I) with displacement ellipsoids shown at the 50% probability level.

Crystal data

C25H34O8·H2OF(000) = 1032
Mr = 480.54Dx = 1.322 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 17248 reflections
a = 7.2672 (15) Åθ = 3.1–27.5°
b = 16.606 (3) ŵ = 0.10 mm1
c = 20.009 (4) ÅT = 293 K
V = 2414.7 (8) Å3Prism, colourless
Z = 40.16 × 0.14 × 0.13 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer2562 reflections with I > 2σ(I)
Radiation source: rotating anodeRint = 0.051
graphiteθmax = 26.5°, θmin = 3.1°
oscillation scansh = −8→9
21231 measured reflectionsk = −20→20
2848 independent reflectionsl = −25→25

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106H-atom parameters constrained
S = 1.06w = 1/[σ2(Fo2) + (0.063P)2 + 0.2837P] where P = (Fo2 + 2Fc2)/3
2848 reflections(Δ/σ)max < 0.001
309 parametersΔρmax = 0.16 e Å3
0 restraintsΔρmin = −0.17 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/Ueq
O1−0.0416 (3)0.95164 (11)1.23851 (7)0.0557 (5)
O2−0.0242 (3)1.00698 (11)0.89550 (9)0.0653 (6)
H2−0.11561.03370.90490.098*
O30.0626 (3)0.71841 (10)0.80452 (8)0.0564 (5)
H3A0.07230.67980.77920.085*
O40.2230 (3)0.83520 (14)0.67050 (8)0.0713 (6)
O5−0.1210 (3)0.82035 (12)0.62841 (8)0.0603 (5)
O60.0212 (3)0.72295 (11)0.57042 (8)0.0611 (5)
O70.0666 (3)0.85527 (12)0.34091 (8)0.0658 (6)
H70.04740.88890.31170.099*
O8−0.1085 (3)0.93713 (12)0.40118 (10)0.0690 (6)
O90.0883 (3)0.57919 (13)0.73352 (10)0.0763 (6)
H2W0.04630.56720.69510.114*
H1W0.20190.56900.73920.114*
C1−0.1098 (3)0.96647 (15)1.06144 (10)0.0436 (5)
H1A−0.18310.99911.03130.052*
H1B−0.16300.91291.06240.052*
C2−0.1196 (4)1.00276 (15)1.13148 (11)0.0520 (6)
H2B−0.08031.05851.12990.062*
H2C−0.24591.00151.14720.062*
C3−0.0006 (4)0.95744 (14)1.17876 (10)0.0444 (5)
C40.1676 (4)0.92345 (15)1.15279 (11)0.0448 (5)
H4A0.24770.89841.18250.054*
C50.2140 (3)0.92622 (13)1.08788 (10)0.0374 (5)
C60.4020 (3)0.90065 (16)1.06572 (11)0.0477 (6)
H6A0.46260.87271.10220.057*
H6B0.47420.94811.05520.057*
C70.3970 (3)0.84573 (15)1.00483 (10)0.0458 (5)
H7A0.34400.79431.01740.055*
H7B0.52170.83610.98950.055*
C80.2841 (3)0.88213 (12)0.94764 (10)0.0339 (4)
H8A0.34390.93150.93200.041*
C90.2692 (3)0.82262 (13)0.88998 (10)0.0369 (4)
H9A0.20570.77500.90740.044*
C100.4473 (4)0.79267 (17)0.85697 (12)0.0535 (6)
H10A0.50270.74970.88290.064*
H10B0.53550.83610.85220.064*
C110.3832 (4)0.76156 (16)0.78761 (12)0.0549 (7)
H11A0.45280.78740.75220.066*
H11B0.40110.70380.78440.066*
C120.1772 (3)0.78255 (13)0.78154 (10)0.0418 (5)
C130.1533 (3)0.85407 (12)0.83136 (9)0.0356 (5)
C140.2382 (4)0.93041 (13)0.80015 (11)0.0478 (6)
H14A0.22400.97480.83040.072*
H14B0.17680.94240.75890.072*
H14C0.36660.92150.79170.072*
C15−0.0418 (3)0.86831 (17)0.85699 (10)0.0447 (5)
H15A−0.09550.81700.86940.054*
H15B−0.11550.89070.82110.054*
C16−0.0500 (3)0.92549 (15)0.91754 (11)0.0445 (5)
H16A−0.17380.92160.93670.053*
C170.0888 (3)0.90217 (12)0.97298 (9)0.0327 (4)
H17A0.04210.85120.99080.039*
C180.0874 (3)0.96102 (12)1.03428 (9)0.0343 (4)
C190.1631 (4)1.04641 (13)1.01880 (11)0.0494 (6)
H19A0.15871.07871.05860.074*
H19B0.08931.07100.98460.074*
H19C0.28811.04231.00360.074*
C200.1216 (4)0.80295 (14)0.70948 (10)0.0484 (6)
C21−0.0732 (4)0.78122 (19)0.68959 (11)0.0589 (7)
H21A−0.08330.72330.68410.071*
H21B−0.15780.79760.72450.071*
C22−0.0565 (3)0.78637 (15)0.57212 (11)0.0449 (5)
C23−0.1019 (4)0.83901 (14)0.51351 (10)0.0453 (5)
H23A−0.06840.89410.52410.054*
H23B−0.23370.83750.50600.054*
C24−0.0045 (4)0.81402 (14)0.45007 (11)0.0491 (6)
H24A0.12530.80640.45950.059*
H24B−0.05400.76290.43490.059*
C25−0.0252 (4)0.87517 (15)0.39558 (11)0.0466 (5)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0697 (12)0.0668 (11)0.0306 (8)−0.0100 (10)0.0046 (8)0.0002 (7)
O20.0894 (15)0.0594 (11)0.0469 (10)0.0358 (11)−0.0174 (10)0.0003 (8)
O30.0850 (14)0.0468 (9)0.0373 (8)−0.0218 (9)0.0110 (9)−0.0018 (7)
O40.0798 (14)0.0982 (15)0.0358 (9)−0.0302 (13)0.0077 (9)0.0125 (9)
O50.0673 (12)0.0787 (12)0.0349 (8)0.0154 (11)0.0019 (8)−0.0053 (8)
O60.0848 (14)0.0542 (10)0.0443 (9)0.0136 (10)0.0007 (9)−0.0003 (8)
O70.0914 (15)0.0696 (12)0.0363 (8)0.0176 (12)0.0047 (10)0.0010 (8)
O80.0811 (14)0.0663 (12)0.0597 (11)0.0290 (12)0.0072 (11)0.0108 (9)
O90.0737 (14)0.0851 (14)0.0703 (12)−0.0039 (13)−0.0130 (12)−0.0341 (11)
C10.0407 (12)0.0587 (13)0.0314 (10)0.0081 (11)0.0005 (9)−0.0009 (9)
C20.0586 (15)0.0618 (14)0.0357 (11)0.0119 (13)0.0065 (11)−0.0032 (10)
C30.0564 (14)0.0447 (11)0.0321 (10)−0.0107 (11)0.0000 (10)−0.0025 (9)
C40.0513 (14)0.0504 (12)0.0328 (10)−0.0016 (11)−0.0084 (10)0.0051 (9)
C50.0381 (11)0.0396 (10)0.0345 (10)−0.0028 (9)−0.0082 (9)0.0011 (8)
C60.0396 (12)0.0659 (14)0.0378 (11)0.0060 (11)−0.0101 (10)0.0008 (10)
C70.0392 (12)0.0571 (13)0.0411 (11)0.0125 (11)−0.0062 (10)0.0020 (10)
C80.0311 (10)0.0388 (10)0.0319 (9)0.0013 (9)−0.0021 (8)0.0020 (8)
C90.0383 (11)0.0375 (10)0.0349 (10)0.0039 (9)0.0009 (9)0.0019 (8)
C100.0490 (14)0.0601 (14)0.0516 (13)0.0175 (12)0.0045 (11)−0.0039 (11)
C110.0634 (17)0.0563 (14)0.0450 (13)0.0122 (13)0.0094 (13)−0.0054 (11)
C120.0536 (14)0.0412 (11)0.0307 (10)−0.0060 (10)0.0060 (9)0.0007 (9)
C130.0394 (11)0.0387 (10)0.0287 (9)−0.0012 (9)0.0012 (8)0.0017 (8)
C140.0596 (15)0.0401 (11)0.0436 (12)−0.0036 (12)−0.0009 (11)0.0081 (9)
C150.0370 (12)0.0667 (14)0.0303 (9)0.0017 (11)−0.0048 (9)−0.0044 (10)
C160.0349 (11)0.0643 (14)0.0343 (10)0.0118 (11)−0.0054 (9)−0.0039 (10)
C170.0320 (10)0.0371 (10)0.0289 (9)−0.0002 (8)−0.0023 (8)0.0022 (7)
C180.0379 (11)0.0362 (10)0.0286 (9)0.0023 (9)−0.0016 (8)0.0038 (8)
C190.0647 (16)0.0405 (11)0.0431 (12)−0.0053 (12)−0.0013 (11)0.0029 (9)
C200.0634 (16)0.0528 (13)0.0290 (10)−0.0045 (12)0.0071 (11)−0.0016 (9)
C210.0637 (17)0.0807 (18)0.0322 (11)−0.0067 (15)0.0042 (11)−0.0002 (12)
C220.0436 (12)0.0530 (13)0.0380 (11)−0.0041 (11)−0.0010 (10)−0.0058 (10)
C230.0470 (13)0.0496 (12)0.0394 (11)0.0029 (11)−0.0034 (10)−0.0015 (9)
C240.0617 (15)0.0470 (12)0.0387 (11)0.0075 (12)−0.0039 (11)−0.0013 (10)
C250.0501 (14)0.0531 (13)0.0366 (11)0.0027 (12)−0.0061 (10)−0.0042 (10)

Geometric parameters (Å, °)

O1—C31.236 (3)C9—C101.536 (3)
O2—C161.436 (3)C9—H9A0.9800
O2—H20.8200C10—C111.552 (4)
O3—C121.428 (3)C10—H10A0.9700
O3—H3A0.8200C10—H10B0.9700
O4—C201.199 (3)C11—C121.542 (4)
O5—C221.344 (3)C11—H11A0.9700
O5—C211.429 (3)C11—H11B0.9700
O6—C221.195 (3)C12—C201.535 (3)
O7—C251.323 (3)C12—C131.560 (3)
O7—H70.8200C13—C151.526 (3)
O8—C251.199 (3)C13—C141.542 (3)
O9—H2W0.8502C14—H14A0.9600
O9—H1W0.8500C14—H14B0.9600
C1—C21.527 (3)C14—H14C0.9600
C1—C181.536 (3)C15—C161.540 (3)
C1—H1A0.9700C15—H15A0.9700
C1—H1B0.9700C15—H15B0.9700
C2—C31.486 (4)C16—C171.548 (3)
C2—H2B0.9700C16—H16A0.9800
C2—H2C0.9700C17—C181.568 (3)
C3—C41.443 (4)C17—H17A0.9800
C4—C51.343 (3)C18—C191.552 (3)
C4—H4A0.9300C19—H19A0.9600
C5—C61.498 (3)C19—H19B0.9600
C5—C181.526 (3)C19—H19C0.9600
C6—C71.522 (3)C20—C211.514 (4)
C6—H6A0.9700C21—H21A0.9700
C6—H6B0.9700C21—H21B0.9700
C7—C81.532 (3)C22—C231.499 (3)
C7—H7A0.9700C23—C241.511 (3)
C7—H7B0.9700C23—H23A0.9700
C8—C91.523 (3)C23—H23B0.9700
C8—C171.543 (3)C24—C251.498 (3)
C8—H8A0.9800C24—H24A0.9700
C9—C131.536 (3)C24—H24B0.9700
C16—O2—H2109.5C15—C13—C14112.4 (2)
C12—O3—H3A109.5C9—C13—C14111.68 (19)
C22—O5—C21116.3 (2)C15—C13—C12115.87 (19)
C25—O7—H7109.5C9—C13—C1299.67 (16)
H2W—O9—H1W115.0C14—C13—C12108.81 (16)
C2—C1—C18113.05 (19)C13—C14—H14A109.5
C2—C1—H1A109.0C13—C14—H14B109.5
C18—C1—H1A109.0H14A—C14—H14B109.5
C2—C1—H1B109.0C13—C14—H14C109.5
C18—C1—H1B109.0H14A—C14—H14C109.5
H1A—C1—H1B107.8H14B—C14—H14C109.5
C3—C2—C1110.9 (2)C13—C15—C16113.31 (18)
C3—C2—H2B109.5C13—C15—H15A108.9
C1—C2—H2B109.5C16—C15—H15A108.9
C3—C2—H2C109.5C13—C15—H15B108.9
C1—C2—H2C109.5C16—C15—H15B108.9
H2B—C2—H2C108.0H15A—C15—H15B107.7
O1—C3—C4121.4 (2)O2—C16—C15109.54 (19)
O1—C3—C2121.0 (2)O2—C16—C17111.77 (19)
C4—C3—C2117.49 (19)C15—C16—C17112.59 (18)
C5—C4—C3123.2 (2)O2—C16—H16A107.6
C5—C4—H4A118.4C15—C16—H16A107.6
C3—C4—H4A118.4C17—C16—H16A107.6
C4—C5—C6120.4 (2)C8—C17—C16114.68 (16)
C4—C5—C18122.8 (2)C8—C17—C18113.40 (17)
C6—C5—C18116.67 (18)C16—C17—C18113.60 (17)
C5—C6—C7112.63 (19)C8—C17—H17A104.6
C5—C6—H6A109.1C16—C17—H17A104.6
C7—C6—H6A109.1C18—C17—H17A104.6
C5—C6—H6B109.1C5—C18—C1109.64 (16)
C7—C6—H6B109.1C5—C18—C19105.83 (18)
H6A—C6—H6B107.8C1—C18—C19110.34 (19)
C6—C7—C8111.99 (18)C5—C18—C17108.04 (16)
C6—C7—H7A109.2C1—C18—C17108.62 (17)
C8—C7—H7A109.2C19—C18—C17114.26 (16)
C6—C7—H7B109.2C18—C19—H19A109.5
C8—C7—H7B109.2C18—C19—H19B109.5
H7A—C7—H7B107.9H19A—C19—H19B109.5
C9—C8—C7110.37 (17)C18—C19—H19C109.5
C9—C8—C17108.86 (17)H19A—C19—H19C109.5
C7—C8—C17109.39 (16)H19B—C19—H19C109.5
C9—C8—H8A109.4O4—C20—C21120.7 (2)
C7—C8—H8A109.4O4—C20—C12123.2 (3)
C17—C8—H8A109.4C21—C20—C12116.1 (2)
C8—C9—C13113.40 (17)O5—C21—C20110.1 (2)
C8—C9—C10118.41 (19)O5—C21—H21A109.6
C13—C9—C10104.11 (17)C20—C21—H21A109.6
C8—C9—H9A106.7O5—C21—H21B109.6
C13—C9—H9A106.7C20—C21—H21B109.6
C10—C9—H9A106.7H21A—C21—H21B108.2
C9—C10—C11103.9 (2)O6—C22—O5123.9 (2)
C9—C10—H10A111.0O6—C22—C23126.5 (2)
C11—C10—H10A111.0O5—C22—C23109.5 (2)
C9—C10—H10B111.0C22—C23—C24113.2 (2)
C11—C10—H10B111.0C22—C23—H23A108.9
H10A—C10—H10B109.0C24—C23—H23A108.9
C12—C11—C10106.6 (2)C22—C23—H23B108.9
C12—C11—H11A110.4C24—C23—H23B108.9
C10—C11—H11A110.4H23A—C23—H23B107.8
C12—C11—H11B110.4C25—C24—C23112.2 (2)
C10—C11—H11B110.4C25—C24—H24A109.2
H11A—C11—H11B108.6C23—C24—H24A109.2
O3—C12—C20108.3 (2)C25—C24—H24B109.2
O3—C12—C11111.9 (2)C23—C24—H24B109.2
C20—C12—C11112.3 (2)H24A—C24—H24B107.9
O3—C12—C13107.28 (17)O8—C25—O7123.1 (2)
C20—C12—C13113.75 (18)O8—C25—C24124.4 (2)
C11—C12—C13103.30 (19)O7—C25—C24112.4 (2)
C15—C13—C9107.79 (16)
C18—C1—C2—C3−55.5 (3)C13—C15—C16—C17−49.1 (3)
C1—C2—C3—O1−148.7 (2)C9—C8—C17—C16−49.2 (2)
C1—C2—C3—C433.7 (3)C7—C8—C17—C16−169.87 (18)
O1—C3—C4—C5177.8 (2)C9—C8—C17—C18178.04 (15)
C2—C3—C4—C5−4.7 (4)C7—C8—C17—C1857.4 (2)
C3—C4—C5—C6171.1 (2)O2—C16—C17—C8−78.2 (2)
C3—C4—C5—C18−4.0 (4)C15—C16—C17—C845.6 (3)
C4—C5—C6—C7134.0 (2)O2—C16—C17—C1854.4 (2)
C18—C5—C6—C7−50.7 (3)C15—C16—C17—C18178.24 (19)
C5—C6—C7—C852.3 (3)C4—C5—C18—C1−17.2 (3)
C6—C7—C8—C9−175.34 (19)C6—C5—C18—C1167.61 (19)
C6—C7—C8—C17−55.6 (3)C4—C5—C18—C19101.8 (2)
C7—C8—C9—C13178.47 (18)C6—C5—C18—C19−73.4 (2)
C17—C8—C9—C1358.4 (2)C4—C5—C18—C17−135.4 (2)
C7—C8—C9—C10−59.1 (3)C6—C5—C18—C1749.4 (2)
C17—C8—C9—C10−179.18 (19)C2—C1—C18—C546.3 (3)
C8—C9—C10—C11−159.65 (19)C2—C1—C18—C19−69.9 (2)
C13—C9—C10—C11−32.7 (2)C2—C1—C18—C17164.16 (18)
C9—C10—C11—C125.4 (3)C8—C17—C18—C5−52.8 (2)
C10—C11—C12—O3−91.9 (2)C16—C17—C18—C5173.95 (18)
C10—C11—C12—C20146.2 (2)C8—C17—C18—C1−171.64 (17)
C10—C11—C12—C1323.2 (2)C16—C17—C18—C155.1 (2)
C8—C9—C13—C15−62.0 (2)C8—C17—C18—C1964.7 (2)
C10—C9—C13—C15168.0 (2)C16—C17—C18—C19−68.6 (2)
C8—C9—C13—C1461.9 (2)O3—C12—C20—O4−156.6 (3)
C10—C9—C13—C14−68.2 (2)C11—C12—C20—O4−32.6 (3)
C8—C9—C13—C12176.70 (18)C13—C12—C20—O484.3 (3)
C10—C9—C13—C1246.7 (2)O3—C12—C20—C2124.4 (3)
O3—C12—C13—C15−39.4 (3)C11—C12—C20—C21148.4 (2)
C20—C12—C13—C1580.3 (2)C13—C12—C20—C21−94.7 (3)
C11—C12—C13—C15−157.70 (19)C22—O5—C21—C2079.2 (3)
O3—C12—C13—C975.9 (2)O4—C20—C21—O5−13.1 (4)
C20—C12—C13—C9−164.4 (2)C12—C20—C21—O5165.9 (2)
C11—C12—C13—C9−42.4 (2)C21—O5—C22—O67.3 (4)
O3—C12—C13—C14−167.12 (19)C21—O5—C22—C23−174.2 (2)
C20—C12—C13—C14−47.4 (3)O6—C22—C23—C24−12.4 (4)
C11—C12—C13—C1474.6 (2)O5—C22—C23—C24169.1 (2)
C9—C13—C15—C1655.8 (3)C22—C23—C24—C25−170.0 (2)
C14—C13—C15—C16−67.6 (2)C23—C24—C25—O80.3 (4)
C12—C13—C15—C16166.44 (18)C23—C24—C25—O7177.2 (2)
C13—C15—C16—O275.9 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2···O8i0.822.062.828 (3)155
O3—H3A···O90.821.912.720 (2)170
O7—H7···O1ii0.821.912.716 (2)167
O9—H2W···O2iii0.852.082.884 (3)158
O9—H1W···O1iv0.851.952.795 (3)174

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB5414).

References

  • Fang, L., Zhang, Y. Y., Lehmann, J., Wang, Y., Ji, H. & Ding, D. Y (2007). Bioorg. Med. Chem. Lett.17, 1062–1066. [PubMed]
  • Rigaku/MSC (2005). CrystalClear Rigaku/MSC, The Woodlands, Texas, USA.
  • Schäcke, H., Döcke, W. D. & Asadullah, K. (2002). Pharmacol. Ther.96, 23–43. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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