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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o987.
Published online 2009 April 8. doi:  10.1107/S1600536809011969
PMCID: PMC2977682

11β,17,21-Trihydr­oxy-6α-methyl-3,20-dioxopregna-1,4-dien-21-yl 3-carboxy­propionate

Abstract

The mol­ecule of the title compound, C26H34O8, a prednisolone derivative, contains three six-membered rings (A, B and C) and one five-membered ring (D). Ring A is planar and rings B and C adopt chair conformations, while ring D adopts an envelope conformation with the C atom bonded to the methyl group at the flap. The crystal structure is stabilized by intermolecular O—H(...)O hydrogen bonds

Related literature

For the preparation, see: Anderson et al. (1984 [triangle]). For bond-length data, see Allen et al. (1987 [triangle]).

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Object name is e-65-0o987-scheme1.jpg

Experimental

Crystal data

  • C26H34O8
  • M r = 474.53
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o987-efi1.jpg
  • a = 8.3125 (1) Å
  • b = 10.1765 (1) Å
  • c = 28.8472 (3) Å
  • V = 2440.25 (5) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 0.79 mm−1
  • T = 296 K
  • 0.30 × 0.20 × 0.20 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: none
  • 8346 measured reflections
  • 3397 independent reflections
  • 3365 reflections with I > 2σ(I)
  • R int = 0.018
  • θmax = 58.8°

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.101
  • S = 1.07
  • 3397 reflections
  • 309 parameters
  • H-atom parameters constrained
  • Δρmax = 0.24 e Å−3
  • Δρmin = −0.13 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1388 Friedel pairs
  • Flack parameter: 0.0 (2)

Data collection: SMART (Bruker, 2005 [triangle]); cell refinement: SAINT (Bruker, 2005 [triangle]); data reduction: SAINT; 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: SHELXL97.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809011969/sj2598sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809011969/sj2598Isup2.hkl

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

Acknowledgments

We acknowledge financial assistance from the International Centre for Diffraction Data. We also acknowledge the Innovation Method Funds of the Ministry of Science and Technology of China (grant No. 2008IMO22200).

supplementary crystallographic information

Comment

The title compound,(I)(Fig. 1),is a prednisolone derivative. It is prepared according to the procedure of Anderson et al. (Anderson et al., 1984) and recrystallized from methanol. Its crystal structure is reported here for the first time, Fig, 1.

Bond lengths within the molecule are normal (Allen et al., 1987). The molecule contains three six-membered rings(A/B/C) and one five-membered ring (D). Ring A is planar and ring B and C adopt chair conformations, while ring D adopts an envelope conformation wit hatom C13 at the flap. Rings B, C and D are trans-fused. The dihedral angles between the least-squares planes fitted through all non-H atoms of the rings are A/B = 139.0 (2) °,B/C = 5.9 (2) °, C/D = 7.3 (3) °.

The structure is stablized by intermolecular hydrogen bonds (Table 2), which link the molecules into infinite chains. The hydrogen-bonding arrangement is shown in Fig.2.

Experimental

The title compound was prepared according to the procedure of Anderson et al. (1984). Crystals suitable for data collection were obtained by slow evaporation from methanol solution at 283 K over a period of two weeks.

Refinement

In the presence of significant anomalous scattering effects, Friedel pairs were not merged. the absolute configuration was established based on the Flack parameter 0.0 (2). All the H atoms were constrained to an ideal geometry with C—H distances of 0.98 Å and Uiso(H) = 1.2Ueq(C)for CH; 0.97 Å and Uiso(H) = 1.2Ueq (C)for CH2; 0.96 Å and Uiso(H) = 1.5Ueq(C)for CH3; and 0.82 Å and Uiso(H) = 1.5Ueq(C)for OH atoms.

Figures

Fig. 1.
View of the molecule of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms have been omitted.
Fig. 2.
The molecular packing of (I) viewed along the a axis. Dashed lines indicate the hydrogen bonding interactions.

Crystal data

C26H34O8F(000) = 1016
Mr = 474.53Dx = 1.292 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 8346 reflections
a = 8.3125 (1) Åθ = 3.1–58.8°
b = 10.1765 (1) ŵ = 0.79 mm1
c = 28.8472 (3) ÅT = 296 K
V = 2440.25 (5) Å3Block, colorless
Z = 40.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEX diffractometer3365 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
graphiteθmax = 58.8°, θmin = 3.1°
[var phi] and ω scansh = −9→6
8346 measured reflectionsk = −11→10
3397 independent reflectionsl = −32→30

Refinement

Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038w = 1/[σ2(Fo2) + (0.0538P)2 + 0.6209P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.101(Δ/σ)max < 0.001
S = 1.07Δρmax = 0.24 e Å3
3397 reflectionsΔρmin = −0.13 e Å3
309 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0070 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), 1388 Friedel pairs
Secondary atom site location: difference Fourier mapFlack parameter: 0.0 (2)

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*/Ueq
O1−0.8924 (3)−0.6628 (2)−0.32497 (7)0.0955 (7)
O2−0.90863 (19)−0.50797 (16)−0.09117 (6)0.0600 (4)
H2A−0.9235−0.4642−0.06770.090*
O3−0.5087 (2)−0.12455 (15)−0.12292 (5)0.0553 (4)
H3A−0.4421−0.0651−0.12240.083*
O4−0.4761 (2)−0.1328 (2)−0.00271 (6)0.0762 (6)
O5−0.7026 (3)0.04879 (18)−0.00567 (7)0.0825 (6)
O6−0.5875 (5)0.2234 (3)−0.03398 (9)0.1343 (13)
O7−0.7607 (2)0.41973 (19)0.11378 (7)0.0790 (6)
O8−0.5211 (2)0.51291 (17)0.10461 (6)0.0658 (5)
H8B−0.55160.55770.12650.099*
C1−0.9685 (4)−0.5852 (4)−0.20758 (11)0.0896 (10)
H1A−1.0508−0.5488−0.18990.107*
C2−0.9911 (5)−0.5948 (4)−0.25305 (13)0.0949 (11)
H2B−1.0868−0.5647−0.26600.114*
C3−0.8704 (4)−0.6509 (3)−0.28248 (9)0.0689 (7)
C4−0.7268 (4)−0.6966 (3)−0.26107 (8)0.0641 (7)
H4A−0.6489−0.7351−0.27980.077*
C5−0.6968 (3)−0.6878 (2)−0.21540 (8)0.0574 (6)
C6−0.5400 (4)−0.7281 (3)−0.19360 (9)0.0702 (7)
H6A−0.5652−0.7894−0.16840.084*
C7−0.4647 (3)−0.6065 (2)−0.17175 (8)0.0585 (6)
H7A−0.4334−0.5465−0.19630.070*
H7B−0.3677−0.6325−0.15540.070*
C8−0.5745 (3)−0.5339 (2)−0.13803 (7)0.0457 (5)
H8A−0.5897−0.5879−0.11020.055*
C9−0.7399 (3)−0.5045 (2)−0.15972 (7)0.0449 (5)
H9A−0.7170−0.4452−0.18560.054*
C10−0.8194 (3)−0.6292 (3)−0.18273 (8)0.0614 (7)
C11−0.8511 (3)−0.4250 (2)−0.12729 (7)0.0480 (5)
H11A−0.9444−0.3969−0.14560.058*
C12−0.7685 (3)−0.3014 (2)−0.10898 (7)0.0455 (5)
H12A−0.8361−0.2620−0.08540.055*
H12B−0.7583−0.2387−0.13410.055*
C13−0.6016 (2)−0.3268 (2)−0.08837 (7)0.0404 (5)
C14−0.5006 (3)−0.4029 (2)−0.12406 (7)0.0419 (5)
H14A−0.4994−0.3489−0.15220.050*
C15−0.3304 (3)−0.3969 (3)−0.10427 (8)0.0555 (6)
H15A−0.2510−0.4013−0.12890.067*
H15B−0.3119−0.4687−0.08280.067*
C16−0.3219 (3)−0.2647 (2)−0.07924 (8)0.0553 (6)
H16A−0.2436−0.2078−0.09400.066*
H16B−0.2909−0.2771−0.04710.066*
C17−0.4916 (3)−0.2038 (2)−0.08224 (7)0.0451 (5)
C18−0.6113 (3)−0.3993 (2)−0.04181 (7)0.0522 (5)
H18A−0.6789−0.4752−0.04500.078*
H18B−0.6557−0.3417−0.01880.078*
H18C−0.5055−0.4262−0.03250.078*
C19−0.8682 (6)−0.7359 (3)−0.14756 (11)0.1111 (15)
H19A−0.9158−0.8087−0.16370.167*
H19B−0.9445−0.7002−0.12600.167*
H19C−0.7746−0.7654−0.13110.167*
C20−0.4209 (5)−0.7970 (4)−0.22589 (13)0.1146 (14)
H20A−0.4703−0.8740−0.23880.172*
H20B−0.3269−0.8219−0.20870.172*
H20C−0.3908−0.7383−0.25050.172*
C21−0.5369 (3)−0.1198 (2)−0.04012 (8)0.0492 (5)
C22−0.6658 (5)−0.0208 (3)−0.04765 (10)0.0921 (11)
H22A−0.63140.0412−0.07120.110*
H22B−0.7619−0.0646−0.05880.110*
C23−0.6483 (3)0.1700 (3)−0.00242 (9)0.0626 (6)
C24−0.6815 (3)0.2305 (2)0.04364 (9)0.0610 (6)
H24A−0.79640.24480.04680.073*
H24B−0.64840.17020.06790.073*
C25−0.5967 (4)0.3568 (3)0.04982 (9)0.0732 (8)
H25A−0.62040.41220.02330.088*
H25B−0.48190.33980.04960.088*
C26−0.6364 (3)0.4306 (2)0.09245 (8)0.0535 (6)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.141 (2)0.0889 (15)0.0562 (11)−0.0046 (15)−0.0195 (12)0.0014 (10)
O20.0627 (9)0.0618 (9)0.0556 (9)−0.0188 (8)0.0214 (8)−0.0138 (8)
O30.0654 (10)0.0508 (9)0.0496 (8)−0.0166 (8)−0.0041 (7)0.0053 (7)
O40.0738 (11)0.0993 (15)0.0554 (10)0.0139 (11)−0.0210 (9)−0.0230 (10)
O50.1149 (16)0.0537 (10)0.0791 (12)0.0066 (11)0.0027 (11)−0.0234 (9)
O60.203 (3)0.117 (2)0.0835 (15)−0.056 (2)0.0512 (19)−0.0292 (15)
O70.0697 (12)0.0676 (11)0.0996 (14)−0.0008 (10)0.0157 (11)−0.0215 (10)
O80.0699 (11)0.0586 (10)0.0689 (11)−0.0049 (9)0.0074 (9)−0.0096 (8)
C10.0519 (15)0.121 (3)0.096 (2)−0.0204 (16)0.0057 (14)−0.055 (2)
C20.0768 (19)0.111 (3)0.097 (2)−0.0051 (19)−0.0278 (17)−0.046 (2)
C30.094 (2)0.0590 (15)0.0539 (15)−0.0130 (15)−0.0066 (14)−0.0067 (12)
C40.0861 (18)0.0610 (14)0.0452 (12)−0.0075 (13)0.0079 (12)−0.0080 (11)
C50.0817 (17)0.0459 (12)0.0446 (12)−0.0125 (12)0.0056 (12)−0.0072 (10)
C60.096 (2)0.0558 (15)0.0586 (14)0.0148 (14)−0.0012 (14)−0.0162 (12)
C70.0661 (15)0.0590 (15)0.0504 (12)0.0117 (12)−0.0005 (11)−0.0078 (11)
C80.0581 (12)0.0425 (11)0.0366 (10)0.0012 (10)0.0010 (9)0.0010 (9)
C90.0526 (12)0.0475 (11)0.0346 (10)−0.0101 (10)0.0026 (9)0.0010 (9)
C100.0707 (16)0.0671 (15)0.0463 (12)−0.0268 (13)0.0154 (11)−0.0148 (12)
C110.0427 (11)0.0522 (12)0.0491 (12)−0.0067 (10)0.0006 (9)−0.0028 (10)
C120.0429 (11)0.0462 (11)0.0475 (11)0.0021 (9)0.0019 (9)−0.0050 (9)
C130.0444 (11)0.0423 (10)0.0347 (9)−0.0016 (9)0.0021 (9)−0.0032 (8)
C140.0438 (11)0.0432 (11)0.0388 (10)0.0023 (9)0.0010 (8)0.0011 (8)
C150.0454 (12)0.0651 (14)0.0561 (13)0.0079 (11)−0.0018 (10)−0.0045 (11)
C160.0441 (12)0.0653 (15)0.0565 (13)−0.0061 (11)−0.0040 (10)−0.0041 (11)
C170.0480 (12)0.0471 (11)0.0403 (10)−0.0061 (10)−0.0040 (9)−0.0013 (9)
C180.0594 (14)0.0578 (13)0.0395 (11)−0.0009 (11)0.0023 (10)0.0005 (10)
C190.177 (4)0.074 (2)0.082 (2)−0.067 (2)0.061 (2)−0.0293 (16)
C200.117 (3)0.117 (3)0.110 (3)0.043 (3)−0.017 (2)−0.064 (2)
C210.0519 (12)0.0467 (12)0.0491 (12)−0.0089 (10)−0.0068 (10)−0.0055 (10)
C220.134 (3)0.0685 (17)0.0741 (18)0.0392 (19)−0.0296 (19)−0.0313 (15)
C230.0626 (14)0.0628 (15)0.0626 (15)0.0128 (12)0.0165 (12)−0.0202 (12)
C240.0611 (14)0.0546 (13)0.0672 (14)−0.0023 (12)0.0081 (12)−0.0114 (12)
C250.106 (2)0.0581 (15)0.0559 (14)−0.0167 (16)0.0171 (14)−0.0035 (12)
C260.0596 (14)0.0410 (11)0.0598 (13)0.0061 (11)0.0006 (12)0.0053 (10)

Geometric parameters (Å, °)

O1—C31.245 (3)C11—H11A0.9800
O2—C111.424 (3)C12—C131.531 (3)
O2—H2A0.8200C12—H12A0.9700
O3—C171.431 (3)C12—H12B0.9700
O3—H3A0.8200C13—C181.535 (3)
O4—C211.199 (3)C13—C141.538 (3)
O5—C231.316 (3)C13—C171.561 (3)
O5—C221.436 (3)C14—C151.527 (3)
O6—C231.175 (3)C14—H14A0.9800
O7—C261.208 (3)C15—C161.529 (4)
O8—C261.320 (3)C15—H15A0.9700
O8—H8B0.8200C15—H15B0.9700
C1—C21.329 (5)C16—C171.543 (3)
C1—C101.500 (5)C16—H16A0.9700
C1—H1A0.9300C16—H16B0.9700
C2—C31.433 (5)C17—C211.532 (3)
C2—H2B0.9300C18—H18A0.9600
C3—C41.423 (4)C18—H18B0.9600
C4—C51.344 (3)C18—H18C0.9600
C4—H4A0.9300C19—H19A0.9600
C5—C61.504 (4)C19—H19B0.9600
C5—C101.511 (3)C19—H19C0.9600
C6—C71.524 (4)C20—H20A0.9600
C6—C201.529 (4)C20—H20B0.9600
C6—H6A0.9800C20—H20C0.9600
C7—C81.525 (3)C21—C221.486 (4)
C7—H7A0.9700C22—H22A0.9700
C7—H7B0.9700C22—H22B0.9700
C8—C141.522 (3)C23—C241.490 (4)
C8—C91.540 (3)C24—C251.476 (4)
C8—H8A0.9800C24—H24A0.9700
C9—C111.544 (3)C24—H24B0.9700
C9—C101.576 (3)C25—C261.478 (3)
C9—H9A0.9800C25—H25A0.9700
C10—C191.541 (4)C25—H25B0.9700
C11—C121.528 (3)
C11—O2—H2A109.5C8—C14—C13113.46 (17)
C17—O3—H3A109.5C15—C14—C13103.62 (16)
C23—O5—C22116.7 (3)C8—C14—H14A106.1
C26—O8—H8B109.5C15—C14—H14A106.1
C2—C1—C10124.5 (3)C13—C14—H14A106.1
C2—C1—H1A117.7C14—C15—C16104.76 (18)
C10—C1—H1A117.7C14—C15—H15A110.8
C1—C2—C3121.0 (3)C16—C15—H15A110.8
C1—C2—H2B119.5C14—C15—H15B110.8
C3—C2—H2B119.5C16—C15—H15B110.8
O1—C3—C4121.3 (3)H15A—C15—H15B108.9
O1—C3—C2121.3 (3)C15—C16—C17106.55 (17)
C4—C3—C2117.4 (2)C15—C16—H16A110.4
C5—C4—C3124.0 (3)C17—C16—H16A110.4
C5—C4—H4A118.0C15—C16—H16B110.4
C3—C4—H4A118.0C17—C16—H16B110.4
C4—C5—C6123.5 (2)H16A—C16—H16B108.6
C4—C5—C10120.9 (3)O3—C17—C21108.18 (17)
C6—C5—C10115.6 (2)O3—C17—C16111.29 (18)
C5—C6—C7107.9 (2)C21—C17—C16113.85 (17)
C5—C6—C20115.6 (2)O3—C17—C13107.50 (15)
C7—C6—C20111.0 (3)C21—C17—C13113.13 (17)
C5—C6—H6A107.3C16—C17—C13102.70 (17)
C7—C6—H6A107.3C13—C18—H18A109.5
C20—C6—H6A107.3C13—C18—H18B109.5
C6—C7—C8114.3 (2)H18A—C18—H18B109.5
C6—C7—H7A108.7C13—C18—H18C109.5
C8—C7—H7A108.7H18A—C18—H18C109.5
C6—C7—H7B108.7H18B—C18—H18C109.5
C8—C7—H7B108.7C10—C19—H19A109.5
H7A—C7—H7B107.6C10—C19—H19B109.5
C14—C8—C7110.58 (19)H19A—C19—H19B109.5
C14—C8—C9107.34 (17)C10—C19—H19C109.5
C7—C8—C9111.67 (17)H19A—C19—H19C109.5
C14—C8—H8A109.1H19B—C19—H19C109.5
C7—C8—H8A109.1C6—C20—H20A109.5
C9—C8—H8A109.1C6—C20—H20B109.5
C8—C9—C11112.95 (16)H20A—C20—H20B109.5
C8—C9—C10112.9 (2)C6—C20—H20C109.5
C11—C9—C10115.20 (18)H20A—C20—H20C109.5
C8—C9—H9A104.8H20B—C20—H20C109.5
C11—C9—H9A104.8O4—C21—C22120.7 (2)
C10—C9—H9A104.8O4—C21—C17123.3 (2)
C1—C10—C5112.1 (2)C22—C21—C17116.05 (19)
C1—C10—C19107.9 (3)O5—C22—C21111.4 (2)
C5—C10—C19108.0 (2)O5—C22—H22A109.3
C1—C10—C9107.9 (2)C21—C22—H22A109.3
C5—C10—C9107.33 (19)O5—C22—H22B109.3
C19—C10—C9113.6 (2)C21—C22—H22B109.3
O2—C11—C12112.71 (17)H22A—C22—H22B108.0
O2—C11—C9109.50 (17)O6—C23—O5121.7 (3)
C12—C11—C9111.83 (17)O6—C23—C24125.4 (3)
O2—C11—H11A107.5O5—C23—C24112.8 (2)
C12—C11—H11A107.5C25—C24—C23112.3 (2)
C9—C11—H11A107.5C25—C24—H24A109.1
C11—C12—C13113.76 (18)C23—C24—H24A109.1
C11—C12—H12A108.8C25—C24—H24B109.1
C13—C12—H12A108.8C23—C24—H24B109.1
C11—C12—H12B108.8H24A—C24—H24B107.9
C13—C12—H12B108.8C24—C25—C26115.9 (2)
H12A—C12—H12B107.7C24—C25—H25A108.3
C12—C13—C18111.91 (17)C26—C25—H25A108.3
C12—C13—C14108.65 (16)C24—C25—H25B108.3
C18—C13—C14111.88 (17)C26—C25—H25B108.3
C12—C13—C17116.09 (17)H25A—C25—H25B107.4
C18—C13—C17108.49 (16)O7—C26—O8122.9 (2)
C14—C13—C1799.21 (16)O7—C26—C25124.6 (2)
C8—C14—C15120.54 (19)O8—C26—C25112.4 (2)
C10—C1—C2—C30.5 (6)C11—C12—C13—C17163.05 (17)
C1—C2—C3—O1178.4 (3)C7—C8—C14—C15−53.9 (3)
C1—C2—C3—C40.6 (5)C9—C8—C14—C15−175.90 (17)
O1—C3—C4—C5−179.3 (3)C7—C8—C14—C13−177.51 (17)
C2—C3—C4—C5−1.5 (4)C9—C8—C14—C1360.5 (2)
C3—C4—C5—C6−175.7 (2)C12—C13—C14—C8−59.0 (2)
C3—C4—C5—C101.3 (4)C18—C13—C14—C865.1 (2)
C4—C5—C6—C7117.5 (3)C17—C13—C14—C8179.37 (16)
C10—C5—C6—C7−59.6 (3)C12—C13—C14—C15168.57 (18)
C4—C5—C6—C20−7.4 (4)C18—C13—C14—C15−67.4 (2)
C10—C5—C6—C20175.5 (3)C17—C13—C14—C1546.91 (19)
C5—C6—C7—C853.9 (3)C8—C14—C15—C16−160.51 (19)
C20—C6—C7—C8−178.5 (3)C13—C14—C15—C16−32.3 (2)
C6—C7—C8—C14−170.77 (19)C14—C15—C16—C174.3 (2)
C6—C7—C8—C9−51.3 (3)C15—C16—C17—O3−90.0 (2)
C14—C8—C9—C11−55.8 (2)C15—C16—C17—C21147.40 (19)
C7—C8—C9—C11−177.16 (18)C15—C16—C17—C1324.7 (2)
C14—C8—C9—C10171.28 (17)C12—C13—C17—O3−42.1 (2)
C7—C8—C9—C1049.9 (2)C18—C13—C17—O3−169.09 (17)
C2—C1—C10—C5−0.7 (5)C14—C13—C17—O374.02 (19)
C2—C1—C10—C19−119.6 (4)C12—C13—C17—C2177.3 (2)
C2—C1—C10—C9117.3 (4)C18—C13—C17—C21−49.7 (2)
C4—C5—C10—C1−0.2 (4)C14—C13—C17—C21−166.61 (17)
C6—C5—C10—C1177.0 (2)C12—C13—C17—C16−159.55 (17)
C4—C5—C10—C19118.6 (3)C18—C13—C17—C1673.4 (2)
C6—C5—C10—C19−64.2 (3)C14—C13—C17—C16−43.45 (18)
C4—C5—C10—C9−118.5 (2)O3—C17—C21—O4−147.7 (2)
C6—C5—C10—C958.7 (3)C16—C17—C21—O4−23.4 (3)
C8—C9—C10—C1−173.07 (19)C13—C17—C21—O493.4 (3)
C11—C9—C10—C155.1 (3)O3—C17—C21—C2233.7 (3)
C8—C9—C10—C5−52.0 (2)C16—C17—C21—C22157.9 (2)
C11—C9—C10—C5176.16 (19)C13—C17—C21—C22−85.3 (3)
C8—C9—C10—C1967.3 (3)C23—O5—C22—C21104.9 (3)
C11—C9—C10—C19−64.5 (3)O4—C21—C22—O5−0.8 (4)
C8—C9—C11—O2−73.8 (2)C17—C21—C22—O5177.9 (2)
C10—C9—C11—O258.0 (2)C22—O5—C23—O67.7 (5)
C8—C9—C11—C1251.9 (2)C22—O5—C23—C24−175.6 (2)
C10—C9—C11—C12−176.30 (18)O6—C23—C24—C25−13.2 (5)
O2—C11—C12—C1373.8 (2)O5—C23—C24—C25170.2 (3)
C9—C11—C12—C13−50.1 (2)C23—C24—C25—C26173.7 (2)
C11—C12—C13—C18−71.7 (2)C24—C25—C26—O7−24.4 (4)
C11—C12—C13—C1452.4 (2)C24—C25—C26—O8156.8 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
O2—H2A···O4i0.822.303.115 (2)172
O3—H3A···O7ii0.822.132.943 (2)173
O8—H8B···O1iii0.821.822.640 (3)176

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: SJ2598).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Anderson, B. D., Conradi, R. A. & Lambert, W. J. (1984). J. Pharm. Sci 73, 604–611. [PubMed]
  • Bruker (2005). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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