organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

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

aInstitute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, 1 Xiannong tan street, Beijing 100050, People's Republic of China
*Correspondence e-mail: luy@imm.ac.cn

(Received 17 March 2009; accepted 31 March 2009; online 8 April 2009)

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[Anderson, B. D., Conradi, R. A. & Lambert, W. J. (1984). J. Pharm. Sci. 73, 604-611.]). For bond-length data, see Allen et al. (1987[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.]).

[Scheme 1]

Experimental

Crystal data
  • C26H34O8

  • Mr = 474.53

  • Orthorhombic, P 21 21 21

  • 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)

  • Rint = 0.018

  • θmax = 58.8°

Refinement
  • R[F2 > 2σ(F2)] = 0.038

  • wR(F2) = 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[Flack, H. D. (1983). Acta Cryst. A39, 876-881.]), 1388 Friedel pairs

  • Flack parameter: 0.0 (2)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O2—H2A⋯O4i 0.82 2.30 3.115 (2) 172
O3—H3A⋯O7ii 0.82 2.13 2.943 (2) 173
O8—H8B⋯O1iii 0.82 1.82 2.640 (3) 176
Symmetry codes: (i) [x-{\script{1\over 2}}, -y-{\script{1\over 2}}, -z]; (ii) [x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]; (iii) [-x-{\script{3\over 2}}, -y, z+{\script{1\over 2}}].

Data collection: SMART (Bruker, 2005[Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2005[Bruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

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.

Related literature top

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

Experimental top

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 top

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.

Computing details top

Data collection: SMART (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] 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.
[Figure 2] Fig. 2. The molecular packing of (I) viewed along the a axis. Dashed lines indicate the hydrogen bonding interactions.
11β,17,21-Trihydroxy-6α-methyl-3,20-dioxopregna-1,4-dien-21-yl 3-carboxypropionate top
Crystal data top
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 top
Bruker SMART APEX
diffractometer
3365 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 58.8°, θmin = 3.1°
ϕ and ω scansh = 96
8346 measured reflectionsk = 1110
3397 independent reflectionsl = 3230
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.038 w = 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 mapAbsolute structure parameter: 0.0 (2)
Crystal data top
C26H34O8V = 2440.25 (5) Å3
Mr = 474.53Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 8.3125 (1) ŵ = 0.79 mm1
b = 10.1765 (1) ÅT = 296 K
c = 28.8472 (3) Å0.30 × 0.20 × 0.20 mm
Data collection top
Bruker SMART APEX
diffractometer
3365 reflections with I > 2σ(I)
8346 measured reflectionsRint = 0.018
3397 independent reflectionsθmax = 58.8°
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.101Δρmax = 0.24 e Å3
S = 1.07Δρmin = 0.13 e Å3
3397 reflectionsAbsolute structure: Flack (1983), 1388 Friedel pairs
309 parametersAbsolute structure parameter: 0.0 (2)
0 restraints
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*/Ueq
O10.8924 (3)0.6628 (2)0.32497 (7)0.0955 (7)
O20.90863 (19)0.50797 (16)0.09117 (6)0.0600 (4)
H2A0.92350.46420.06770.090*
O30.5087 (2)0.12455 (15)0.12292 (5)0.0553 (4)
H3A0.44210.06510.12240.083*
O40.4761 (2)0.1328 (2)0.00271 (6)0.0762 (6)
O50.7026 (3)0.04879 (18)0.00567 (7)0.0825 (6)
O60.5875 (5)0.2234 (3)0.03398 (9)0.1343 (13)
O70.7607 (2)0.41973 (19)0.11378 (7)0.0790 (6)
O80.5211 (2)0.51291 (17)0.10461 (6)0.0658 (5)
H8B0.55160.55770.12650.099*
C10.9685 (4)0.5852 (4)0.20758 (11)0.0896 (10)
H1A1.05080.54880.18990.107*
C20.9911 (5)0.5948 (4)0.25305 (13)0.0949 (11)
H2B1.08680.56470.26600.114*
C30.8704 (4)0.6509 (3)0.28248 (9)0.0689 (7)
C40.7268 (4)0.6966 (3)0.26107 (8)0.0641 (7)
H4A0.64890.73510.27980.077*
C50.6968 (3)0.6878 (2)0.21540 (8)0.0574 (6)
C60.5400 (4)0.7281 (3)0.19360 (9)0.0702 (7)
H6A0.56520.78940.16840.084*
C70.4647 (3)0.6065 (2)0.17175 (8)0.0585 (6)
H7A0.43340.54650.19630.070*
H7B0.36770.63250.15540.070*
C80.5745 (3)0.5339 (2)0.13803 (7)0.0457 (5)
H8A0.58970.58790.11020.055*
C90.7399 (3)0.5045 (2)0.15972 (7)0.0449 (5)
H9A0.71700.44520.18560.054*
C100.8194 (3)0.6292 (3)0.18273 (8)0.0614 (7)
C110.8511 (3)0.4250 (2)0.12729 (7)0.0480 (5)
H11A0.94440.39690.14560.058*
C120.7685 (3)0.3014 (2)0.10898 (7)0.0455 (5)
H12A0.83610.26200.08540.055*
H12B0.75830.23870.13410.055*
C130.6016 (2)0.3268 (2)0.08837 (7)0.0404 (5)
C140.5006 (3)0.4029 (2)0.12406 (7)0.0419 (5)
H14A0.49940.34890.15220.050*
C150.3304 (3)0.3969 (3)0.10427 (8)0.0555 (6)
H15A0.25100.40130.12890.067*
H15B0.31190.46870.08280.067*
C160.3219 (3)0.2647 (2)0.07924 (8)0.0553 (6)
H16A0.24360.20780.09400.066*
H16B0.29090.27710.04710.066*
C170.4916 (3)0.2038 (2)0.08224 (7)0.0451 (5)
C180.6113 (3)0.3993 (2)0.04181 (7)0.0522 (5)
H18A0.67890.47520.04500.078*
H18B0.65570.34170.01880.078*
H18C0.50550.42620.03250.078*
C190.8682 (6)0.7359 (3)0.14756 (11)0.1111 (15)
H19A0.91580.80870.16370.167*
H19B0.94450.70020.12600.167*
H19C0.77460.76540.13110.167*
C200.4209 (5)0.7970 (4)0.22589 (13)0.1146 (14)
H20A0.47030.87400.23880.172*
H20B0.32690.82190.20870.172*
H20C0.39080.73830.25050.172*
C210.5369 (3)0.1198 (2)0.04012 (8)0.0492 (5)
C220.6658 (5)0.0208 (3)0.04765 (10)0.0921 (11)
H22A0.63140.04120.07120.110*
H22B0.76190.06460.05880.110*
C230.6483 (3)0.1700 (3)0.00242 (9)0.0626 (6)
C240.6815 (3)0.2305 (2)0.04364 (9)0.0610 (6)
H24A0.79640.24480.04680.073*
H24B0.64840.17020.06790.073*
C250.5967 (4)0.3568 (3)0.04982 (9)0.0732 (8)
H25A0.62040.41220.02330.088*
H25B0.48190.33980.04960.088*
C260.6364 (3)0.4306 (2)0.09245 (8)0.0535 (6)
Atomic displacement parameters (Å2) top
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, º) top
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—C1553.9 (3)
C1—C2—C3—C40.6 (5)C9—C8—C14—C15175.90 (17)
O1—C3—C4—C5179.3 (3)C7—C8—C14—C13177.51 (17)
C2—C3—C4—C51.5 (4)C9—C8—C14—C1360.5 (2)
C3—C4—C5—C6175.7 (2)C12—C13—C14—C859.0 (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—C759.6 (3)C12—C13—C14—C15168.57 (18)
C4—C5—C6—C207.4 (4)C18—C13—C14—C1567.4 (2)
C10—C5—C6—C20175.5 (3)C17—C13—C14—C1546.91 (19)
C5—C6—C7—C853.9 (3)C8—C14—C15—C16160.51 (19)
C20—C6—C7—C8178.5 (3)C13—C14—C15—C1632.3 (2)
C6—C7—C8—C14170.77 (19)C14—C15—C16—C174.3 (2)
C6—C7—C8—C951.3 (3)C15—C16—C17—O390.0 (2)
C14—C8—C9—C1155.8 (2)C15—C16—C17—C21147.40 (19)
C7—C8—C9—C11177.16 (18)C15—C16—C17—C1324.7 (2)
C14—C8—C9—C10171.28 (17)C12—C13—C17—O342.1 (2)
C7—C8—C9—C1049.9 (2)C18—C13—C17—O3169.09 (17)
C2—C1—C10—C50.7 (5)C14—C13—C17—O374.02 (19)
C2—C1—C10—C19119.6 (4)C12—C13—C17—C2177.3 (2)
C2—C1—C10—C9117.3 (4)C18—C13—C17—C2149.7 (2)
C4—C5—C10—C10.2 (4)C14—C13—C17—C21166.61 (17)
C6—C5—C10—C1177.0 (2)C12—C13—C17—C16159.55 (17)
C4—C5—C10—C19118.6 (3)C18—C13—C17—C1673.4 (2)
C6—C5—C10—C1964.2 (3)C14—C13—C17—C1643.45 (18)
C4—C5—C10—C9118.5 (2)O3—C17—C21—O4147.7 (2)
C6—C5—C10—C958.7 (3)C16—C17—C21—O423.4 (3)
C8—C9—C10—C1173.07 (19)C13—C17—C21—O493.4 (3)
C11—C9—C10—C155.1 (3)O3—C17—C21—C2233.7 (3)
C8—C9—C10—C552.0 (2)C16—C17—C21—C22157.9 (2)
C11—C9—C10—C5176.16 (19)C13—C17—C21—C2285.3 (3)
C8—C9—C10—C1967.3 (3)C23—O5—C22—C21104.9 (3)
C11—C9—C10—C1964.5 (3)O4—C21—C22—O50.8 (4)
C8—C9—C11—O273.8 (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—C24175.6 (2)
C10—C9—C11—C12176.30 (18)O6—C23—C24—C2513.2 (5)
O2—C11—C12—C1373.8 (2)O5—C23—C24—C25170.2 (3)
C9—C11—C12—C1350.1 (2)C23—C24—C25—C26173.7 (2)
C11—C12—C13—C1871.7 (2)C24—C25—C26—O724.4 (4)
C11—C12—C13—C1452.4 (2)C24—C25—C26—O8156.8 (2)
Hydrogen-bond geometry (Å, º) top
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) x1/2, y1/2, z; (ii) x+1/2, y+1/2, z; (iii) x3/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC26H34O8
Mr474.53
Crystal system, space groupOrthorhombic, P212121
Temperature (K)296
a, b, c (Å)8.3125 (1), 10.1765 (1), 28.8472 (3)
V3)2440.25 (5)
Z4
Radiation typeCu Kα
µ (mm1)0.79
Crystal size (mm)0.30 × 0.20 × 0.20
Data collection
DiffractometerBruker SMART APEX
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
8346, 3397, 3365
Rint0.018
θmax (°)58.8
(sin θ/λ)max1)0.555
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.101, 1.07
No. of reflections3397
No. of parameters309
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.13
Absolute structureFlack (1983), 1388 Friedel pairs
Absolute structure parameter0.0 (2)

Computer programs: SMART (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
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)176.4
Symmetry codes: (i) x1/2, y1/2, z; (ii) x+1/2, y+1/2, z; (iii) x3/2, y, z+1/2.
 

Acknowledgements

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).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CrossRef Web of Science Google Scholar
First citationAnderson, B. D., Conradi, R. A. & Lambert, W. J. (1984). J. Pharm. Sci. 73, 604–611.  CrossRef CAS PubMed Web of Science Google Scholar
First citationBruker (2005). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFlack, H. D. (1983). Acta Cryst. A39, 876–881.  CrossRef CAS Web of Science IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds