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The title compound (systematic name: 24-nor-13α,14β,15β,17α-chola-1,5,20-triene-14,15:21,23-diep­oxy-6-hydr­oxy-4,4,8-tri­methyl-3,7,21-trione), C26H30O6, is a semisynthetic derivative of cedrelone, obtained via microwave oxidation. Modification of the parent compound results in a change in the orientation of the furan ring; however, the conformations of the other rings are not altered. The conformations adopted by rings AE are boat, half-chair, twist, envelope and planar, respectively. Motifs R22[10], S(5), C(7) and C(12) are formed through O—H...O and C—H...O hydrogen bonds in the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807039402/wn2184sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807039402/wn2184Isup2.hkl
Contains datablock I

CCDC reference: 222445

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.047
  • wR factor = 0.125
  • Data-to-parameter ratio = 10.2

checkCIF/PLATON results

No syntax errors found



Alert level C WEIGH01_ALERT_1_C Extra text has been found in the _refine_ls_weighting_scheme field. This should be in the _refine_ls_weighting_details field. Weighting scheme given as calc w=1/[\s^2^(Fo^2^)+(0.0777P)^2^] where Weighting scheme identified as calc PLAT412_ALERT_2_C Short Intra XH3 .. XHn H9 .. H18B .. 1.87 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 27.99 From the CIF: _reflns_number_total 2967 Count of symmetry unique reflns 3021 Completeness (_total/calc) 98.21% 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 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K 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 C13 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C17 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 10 ALERT level G = General alerts; check 10 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Cedrelone (Zeumer et al., 2000), one of the major limonoids extracted from Toona ciliata, shows minimum antifeedant activity; however it was reported that its photo and microwave products show enhanced and reduced activity, respectively (Suresh et al., 2002).

The present study reports the crystal structure of a microwave-modified product which has an additional carbonyl group at C21 in the furan ring. This substitution has modified only the furan ring orientation with respect to ring D. The torsion angle, C16—C17—C20—C22, showing the relative orientation of the furan ring with respect to ring D, is 25.5 (4)°, compared to 168.3 (4)° in cedrelone itself.

Ring A is in a boat conformation (Cremer & Pople, 1975). The atoms C3 and C10 deviate by 0.561 (2) Å & 0.405 (2) Å from the plane involving the other atoms of the ring. Ring B takes up a half-chair conformation, the atoms C9 and C8 deviating from the least-squares plane of the other four atoms by 0.530 (2) Å and -0.183 (2) Å. Ring C adopts a twist conformation, with the atoms C11 and C13 deviating from the plane through atoms C8, C9, C12, C14 by -0.789 (3) Å and 0.697 (2) Å. Ring D is in an envelope conformation with C17 as the flap atom, lying 0.543 (4) Å from the plane of the remaining four atoms. Ring E is in a planar conformation, the maximum deviation (for atom C22) being 0.045 (4) Å. The ring fusions at the junctions A/B, B/C and C/D are quasi-trans, trans and trans, respectively, as seen from the endocyclic torsion angles.

The packing of the molecules in the crystal structure (Fig. 2) is achieved through a network of O—H···O and C—H···O hydrogen bonds (Table 1). An S(5) motif is generated through the O6—H6···O7 intramolecular hydrogen bond. Three chain motifs C(7),C(7) and C(12) are generated through hydrogen bonds O6—H6···O3 (-1/2 + x, 3/2 - y, -z), C28—H28C···O7 (1/2 + x,3/2 - y,-z) and C2—H2···O21(1/2 + x, 1/2 - y,-z). These in turn generate a ring motif R22[10] (Bernstein et al.,1995).

Related literature top

For related literature, see: Hodges et al. (1963); Zeumer et al. (2000); Geetha Gopalakrishnan et al. (2000, 2001).

For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975); Harris et al. (1968); Henderson et al. (1968); Narayanan et al. (1967); Suresh et al. (2002).

Experimental top

The microwave-oxidized product was obtained through the procedure reported in the literature (Geetha Gopalakrishnan et al., 2000; 2001). Good diffraction quality crystals were obtained from ethyl acetate/hexane (1:1) by slow evaporation.

Refinement top

In the absence of significant anomalous scattering, 1980 Friedel pairs were merged. The enantiomer employed in the refined model was chosen to agree with the accepted configuration of limonoids (Henderson et al., 1968; Narayanan et al., 1967; Harris et al., 1968). Methine and methylene H atoms were constrained to an ideal geometry (C—H = 0.98 and 0.97 Å, respectively), with Uiso(H) = 1.2Ueq(parent atom). Methyl and hydroxyl H hydrogen atoms were placed in geometrically idealized positions (C—H = 0.96 Å and O—H = 0.98 Å) and were constrained to ride on their parent atom with Uiso(H) = 1.5Ueq(C,O).

Structure description top

Cedrelone (Zeumer et al., 2000), one of the major limonoids extracted from Toona ciliata, shows minimum antifeedant activity; however it was reported that its photo and microwave products show enhanced and reduced activity, respectively (Suresh et al., 2002).

The present study reports the crystal structure of a microwave-modified product which has an additional carbonyl group at C21 in the furan ring. This substitution has modified only the furan ring orientation with respect to ring D. The torsion angle, C16—C17—C20—C22, showing the relative orientation of the furan ring with respect to ring D, is 25.5 (4)°, compared to 168.3 (4)° in cedrelone itself.

Ring A is in a boat conformation (Cremer & Pople, 1975). The atoms C3 and C10 deviate by 0.561 (2) Å & 0.405 (2) Å from the plane involving the other atoms of the ring. Ring B takes up a half-chair conformation, the atoms C9 and C8 deviating from the least-squares plane of the other four atoms by 0.530 (2) Å and -0.183 (2) Å. Ring C adopts a twist conformation, with the atoms C11 and C13 deviating from the plane through atoms C8, C9, C12, C14 by -0.789 (3) Å and 0.697 (2) Å. Ring D is in an envelope conformation with C17 as the flap atom, lying 0.543 (4) Å from the plane of the remaining four atoms. Ring E is in a planar conformation, the maximum deviation (for atom C22) being 0.045 (4) Å. The ring fusions at the junctions A/B, B/C and C/D are quasi-trans, trans and trans, respectively, as seen from the endocyclic torsion angles.

The packing of the molecules in the crystal structure (Fig. 2) is achieved through a network of O—H···O and C—H···O hydrogen bonds (Table 1). An S(5) motif is generated through the O6—H6···O7 intramolecular hydrogen bond. Three chain motifs C(7),C(7) and C(12) are generated through hydrogen bonds O6—H6···O3 (-1/2 + x, 3/2 - y, -z), C28—H28C···O7 (1/2 + x,3/2 - y,-z) and C2—H2···O21(1/2 + x, 1/2 - y,-z). These in turn generate a ring motif R22[10] (Bernstein et al.,1995).

For related literature, see: Hodges et al. (1963); Zeumer et al. (2000); Geetha Gopalakrishnan et al. (2000, 2001).

For related literature, see: Bernstein et al. (1995); Cremer & Pople (1975); Harris et al. (1968); Henderson et al. (1968); Narayanan et al. (1967); Suresh et al. (2002).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 and PARST97 (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound, with 30% probability displacement ellipsoids and the atomic numbering scheme. Hydrogen atoms have been omitted.
[Figure 2] Fig. 2. A view of the crystal packing of the title compound. Dashed lines indicate hydrogen bonds. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.
24-nor-13α,14β,15β,17α-chola-1,5,20-triene- 14,15:21,23-diepoxy-6-hydroxy-4,4,8-trimethyl-3,7,21-trione top
Crystal data top
C26H30O6F(000) = 936
Mr = 438.50Dx = 1.311 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 5100 reflections
a = 12.6858 (9) Åθ = 2.2–28.0°
b = 13.1117 (9) ŵ = 0.09 mm1
c = 13.353 (1) ÅT = 293 K
V = 2221.0 (3) Å3Needle, yellow
Z = 40.26 × 0.21 × 0.17 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2967 independent reflections
Radiation source: fine-focus sealed tube2364 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
ω scansθmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1616
Tmin = 0.974, Tmax = 0.985k = 716
14146 measured reflectionsl = 1716
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125H-atom parameters constrained
S = 1.08Calculated w = 1/[σ2(Fo2) + (0.0777P)2]
where P = (Fo2 + 2Fc2)/3
2967 reflections(Δ/σ)max < 0.001
290 parametersΔρmax = 0.24 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C26H30O6V = 2221.0 (3) Å3
Mr = 438.50Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 12.6858 (9) ŵ = 0.09 mm1
b = 13.1117 (9) ÅT = 293 K
c = 13.353 (1) Å0.26 × 0.21 × 0.17 mm
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2967 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
2364 reflections with I > 2σ(I)
Tmin = 0.974, Tmax = 0.985Rint = 0.035
14146 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.125H-atom parameters constrained
S = 1.08Δρmax = 0.24 e Å3
2967 reflectionsΔρmin = 0.19 e Å3
290 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*/Ueq
O30.81936 (15)0.57248 (16)0.04775 (16)0.0540 (5)
O60.49433 (14)0.78724 (13)0.06943 (16)0.0462 (5)
H60.43630.81300.07940.069*
O70.34393 (15)0.73469 (14)0.19410 (15)0.0484 (5)
O150.29074 (16)0.48982 (17)0.35735 (13)0.0534 (5)
O210.0963 (2)0.2091 (2)0.1912 (3)0.1014 (11)
O230.04455 (19)0.2598 (2)0.1022 (2)0.0797 (8)
C10.5936 (2)0.4466 (2)0.0257 (2)0.0449 (6)
H10.55440.38750.01540.054*
C20.6681 (2)0.4702 (2)0.0389 (2)0.0474 (6)
H20.68330.42700.09220.057*
C30.7267 (2)0.5652 (2)0.02574 (19)0.0405 (6)
C40.6621 (2)0.65651 (19)0.00986 (18)0.0375 (5)
C50.57172 (18)0.62388 (19)0.07896 (17)0.0338 (5)
C60.49469 (19)0.68980 (18)0.10440 (18)0.0362 (5)
C70.40724 (19)0.66755 (18)0.17463 (17)0.0353 (5)
C80.40818 (19)0.56473 (19)0.22575 (17)0.0350 (5)
C90.45650 (19)0.48718 (18)0.15132 (18)0.0351 (5)
H90.41370.49520.09070.042*
C100.56963 (18)0.51229 (19)0.11602 (19)0.0360 (5)
C110.4311 (2)0.3790 (2)0.1872 (2)0.0432 (6)
H11A0.44490.37320.25840.052*
H11B0.47530.33010.15230.052*
C120.3141 (2)0.35638 (19)0.1657 (2)0.0434 (6)
H12A0.29070.30120.20880.052*
H12B0.30660.33410.09680.052*
C130.24314 (18)0.45085 (18)0.18341 (18)0.0353 (5)
C140.2988 (2)0.5246 (2)0.25409 (17)0.0372 (5)
C150.2220 (2)0.5690 (2)0.3221 (2)0.0521 (7)
H150.23060.63920.34590.062*
C160.1141 (2)0.5284 (2)0.2979 (2)0.0551 (8)
H16A0.07560.57510.25500.066*
H16B0.07360.51630.35840.066*
C170.1385 (2)0.4279 (2)0.2433 (2)0.0422 (6)
H170.15540.37680.29440.051*
C180.2138 (2)0.5065 (2)0.0863 (2)0.0434 (6)
H18A0.17880.46000.04190.065*
H18B0.27660.53180.05490.065*
H18C0.16770.56250.10150.065*
C190.6576 (2)0.4912 (2)0.1933 (2)0.0519 (7)
H19A0.65760.42010.21050.078*
H19B0.64530.53110.25240.078*
H19C0.72470.50920.16500.078*
C200.0501 (2)0.3867 (2)0.1819 (2)0.0471 (7)
C210.0405 (3)0.2773 (3)0.1616 (3)0.0637 (9)
C220.0315 (2)0.4304 (3)0.1377 (4)0.0765 (11)
H220.04680.49970.14070.092*
C230.0956 (3)0.3537 (3)0.0829 (4)0.0822 (12)
H23A0.16750.35270.10750.099*
H23B0.09650.36830.01170.099*
C280.6164 (2)0.6976 (2)0.0908 (2)0.0513 (7)
H28A0.57380.75660.07790.077*
H28B0.57400.64570.12160.077*
H28C0.67330.71570.13470.077*
C290.7320 (2)0.7357 (2)0.0607 (2)0.0494 (7)
H29A0.68960.79220.08230.074*
H29B0.78430.75930.01420.074*
H29C0.76610.70550.11760.074*
C300.4720 (2)0.5847 (2)0.3232 (2)0.0505 (7)
H30A0.53470.62230.30730.076*
H30B0.49090.52080.35330.076*
H30C0.42970.62340.36920.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0394 (10)0.0535 (11)0.0692 (13)0.0030 (9)0.0126 (9)0.0034 (10)
O60.0425 (10)0.0331 (9)0.0629 (12)0.0020 (8)0.0026 (9)0.0069 (9)
O70.0473 (10)0.0382 (10)0.0597 (12)0.0082 (9)0.0059 (9)0.0002 (9)
O150.0693 (13)0.0627 (13)0.0282 (9)0.0034 (11)0.0059 (8)0.0048 (9)
O210.0861 (18)0.0517 (15)0.166 (3)0.0126 (14)0.017 (2)0.0224 (19)
O230.0543 (13)0.0725 (16)0.112 (2)0.0035 (12)0.0076 (14)0.0265 (16)
C10.0428 (13)0.0369 (14)0.0550 (15)0.0009 (11)0.0022 (12)0.0066 (12)
C20.0475 (15)0.0449 (15)0.0497 (15)0.0020 (13)0.0094 (12)0.0145 (13)
C30.0402 (13)0.0446 (14)0.0368 (12)0.0032 (11)0.0019 (10)0.0023 (11)
C40.0368 (12)0.0366 (13)0.0392 (12)0.0040 (11)0.0006 (10)0.0007 (10)
C50.0329 (11)0.0343 (12)0.0343 (11)0.0034 (10)0.0049 (9)0.0014 (10)
C60.0388 (12)0.0302 (12)0.0395 (13)0.0016 (10)0.0049 (10)0.0024 (10)
C70.0384 (12)0.0325 (12)0.0351 (11)0.0004 (10)0.0059 (10)0.0065 (10)
C80.0381 (12)0.0346 (13)0.0322 (11)0.0015 (11)0.0013 (9)0.0015 (10)
C90.0368 (12)0.0308 (12)0.0378 (12)0.0030 (10)0.0012 (10)0.0026 (10)
C100.0351 (12)0.0325 (12)0.0403 (12)0.0019 (10)0.0011 (10)0.0015 (10)
C110.0458 (14)0.0344 (13)0.0496 (14)0.0072 (11)0.0062 (12)0.0065 (12)
C120.0495 (14)0.0314 (13)0.0494 (14)0.0012 (11)0.0101 (12)0.0022 (11)
C130.0407 (13)0.0325 (12)0.0326 (11)0.0016 (10)0.0062 (10)0.0010 (10)
C140.0451 (13)0.0381 (13)0.0284 (11)0.0029 (11)0.0023 (10)0.0032 (10)
C150.0622 (17)0.0466 (16)0.0474 (15)0.0040 (14)0.0177 (13)0.0122 (13)
C160.0556 (17)0.0500 (16)0.0599 (18)0.0012 (14)0.0230 (14)0.0108 (14)
C170.0443 (13)0.0378 (13)0.0446 (14)0.0016 (12)0.0112 (11)0.0029 (11)
C180.0472 (15)0.0453 (15)0.0377 (13)0.0047 (12)0.0013 (10)0.0048 (12)
C190.0441 (14)0.0576 (18)0.0539 (16)0.0107 (13)0.0051 (12)0.0109 (14)
C200.0410 (13)0.0437 (15)0.0565 (16)0.0018 (12)0.0145 (13)0.0042 (14)
C210.0500 (16)0.0528 (18)0.088 (2)0.0009 (15)0.0083 (17)0.0156 (18)
C220.0462 (17)0.058 (2)0.125 (3)0.0034 (16)0.007 (2)0.011 (2)
C230.0549 (19)0.081 (3)0.111 (3)0.005 (2)0.012 (2)0.001 (2)
C280.0538 (16)0.0568 (18)0.0432 (15)0.0037 (14)0.0000 (12)0.0081 (13)
C290.0430 (14)0.0467 (15)0.0585 (17)0.0114 (13)0.0012 (12)0.0101 (14)
C300.0580 (16)0.0553 (16)0.0382 (14)0.0027 (14)0.0083 (12)0.0035 (13)
Geometric parameters (Å, º) top
O3—C31.216 (3)C12—H12A0.9700
O6—C61.360 (3)C12—H12B0.9700
O6—H60.8200C13—C141.525 (4)
O7—C71.220 (3)C13—C181.533 (3)
O15—C151.436 (4)C13—C171.578 (3)
O15—C141.456 (3)C14—C151.454 (4)
O21—C211.206 (4)C15—C161.503 (4)
O23—C211.359 (4)C15—H150.9800
O23—C231.416 (5)C16—C171.538 (4)
C1—C21.317 (4)C16—H16A0.9700
C1—C101.514 (4)C16—H16B0.9700
C1—H10.9300C17—C201.491 (4)
C2—C31.461 (4)C17—H170.9800
C2—H20.9300C18—H18A0.9600
C3—C41.527 (4)C18—H18B0.9600
C4—C291.526 (3)C18—H18C0.9600
C4—C51.532 (3)C19—H19A0.9600
C4—C281.559 (4)C19—H19B0.9600
C5—C61.348 (3)C19—H19C0.9600
C5—C101.545 (3)C20—C221.323 (4)
C6—C71.482 (3)C20—C211.465 (4)
C7—O71.220 (3)C22—C231.486 (5)
C7—C81.511 (3)C22—H220.9300
C8—C141.531 (4)C23—H23A0.9700
C8—C91.548 (3)C23—H23B0.9700
C8—C301.555 (3)C28—H28A0.9600
C9—C111.531 (3)C28—H28B0.9600
C9—C101.546 (3)C28—H28C0.9600
C9—H90.9800C29—H29A0.9600
C10—C191.545 (4)C29—H29B0.9600
C11—C121.540 (4)C29—H29C0.9600
C11—H11A0.9700C30—H30A0.9600
C11—H11B0.9700C30—H30B0.9600
C12—C131.549 (3)C30—H30C0.9600
C6—O6—H6109.5C15—C14—C8128.6 (2)
C15—O15—C1460.35 (17)O15—C14—C8113.9 (2)
C21—O23—C23108.8 (3)C13—C14—C8119.0 (2)
C2—C1—C10122.2 (2)O15—C15—C1460.51 (17)
C2—C1—H1118.9O15—C15—C16111.5 (3)
C10—C1—H1118.9C14—C15—C16109.5 (2)
C1—C2—C3119.1 (2)O15—C15—H15120.3
C1—C2—H2120.4C14—C15—H15120.3
C3—C2—H2120.4C16—C15—H15120.3
O3—C3—C2122.0 (3)C15—C16—C17102.8 (2)
O3—C3—C4122.2 (2)C15—C16—H16A111.2
C2—C3—C4115.7 (2)C17—C16—H16A111.2
C29—C4—C3111.1 (2)C15—C16—H16B111.2
C29—C4—C5110.9 (2)C17—C16—H16B111.2
C3—C4—C5111.7 (2)H16A—C16—H16B109.1
C29—C4—C28111.4 (2)C20—C17—C16114.9 (2)
C3—C4—C28101.7 (2)C20—C17—C13115.0 (2)
C5—C4—C28109.7 (2)C16—C17—C13104.3 (2)
C6—C5—C4121.0 (2)C20—C17—H17107.4
C6—C5—C10120.9 (2)C16—C17—H17107.4
C4—C5—C10118.1 (2)C13—C17—H17107.4
C5—C6—O6121.2 (2)C13—C18—H18A109.5
C5—C6—C7125.2 (2)C13—C18—H18B109.5
O6—C6—C7113.6 (2)H18A—C18—H18B109.5
O7—C7—C6119.1 (2)C13—C18—H18C109.5
O7—C7—C8123.6 (2)H18A—C18—H18C109.5
C6—C7—C8117.1 (2)H18B—C18—H18C109.5
C7—C8—C14114.3 (2)C10—C19—H19A109.5
C7—C8—C9107.40 (19)C10—C19—H19B109.5
C14—C8—C9106.9 (2)H19A—C19—H19B109.5
C7—C8—C30103.4 (2)C10—C19—H19C109.5
C14—C8—C30108.8 (2)H19A—C19—H19C109.5
C9—C8—C30116.2 (2)H19B—C19—H19C109.5
C11—C9—C10119.2 (2)C22—C20—C21106.1 (3)
C11—C9—C8108.9 (2)C22—C20—C17132.6 (3)
C10—C9—C8115.0 (2)C21—C20—C17121.3 (3)
C11—C9—H9103.9O21—C21—O23122.1 (3)
C10—C9—H9103.9O21—C21—C20128.1 (3)
C8—C9—H9103.9O23—C21—C20109.8 (3)
C1—C10—C5106.3 (2)C20—C22—C23110.7 (3)
C1—C10—C19106.6 (2)C20—C22—H22124.6
C5—C10—C19111.8 (2)C23—C22—H22124.6
C1—C10—C9107.9 (2)O23—C23—C22104.4 (3)
C5—C10—C9108.38 (19)O23—C23—H23A110.9
C19—C10—C9115.4 (2)C22—C23—H23A110.9
C9—C11—C12108.8 (2)O23—C23—H23B110.9
C9—C11—H11A109.9C22—C23—H23B110.9
C12—C11—H11A109.9H23A—C23—H23B108.9
C9—C11—H11B109.9C4—C28—H28A109.5
C12—C11—H11B109.9C4—C28—H28B109.5
H11A—C11—H11B108.3H28A—C28—H28B109.5
C11—C12—C13112.2 (2)C4—C28—H28C109.5
C11—C12—H12A109.2H28A—C28—H28C109.5
C13—C12—H12A109.2H28B—C28—H28C109.5
C11—C12—H12B109.2C4—C29—H29A109.5
C13—C12—H12B109.2C4—C29—H29B109.5
H12A—C12—H12B107.9H29A—C29—H29B109.5
C14—C13—C18109.5 (2)C4—C29—H29C109.5
C14—C13—C12109.4 (2)H29A—C29—H29C109.5
C18—C13—C12113.1 (2)H29B—C29—H29C109.5
C14—C13—C17101.3 (2)C8—C30—H30A109.5
C18—C13—C17108.3 (2)C8—C30—H30B109.5
C12—C13—C17114.4 (2)H30A—C30—H30B109.5
C15—C14—O1559.14 (17)C8—C30—H30C109.5
C15—C14—C13109.3 (2)H30A—C30—H30C109.5
O15—C14—C13110.8 (2)H30B—C30—H30C109.5
C10—C1—C2—C32.8 (4)C11—C12—C13—C1422.2 (3)
C1—C2—C3—O3145.9 (3)C11—C12—C13—C18100.2 (3)
C1—C2—C3—C438.6 (4)C11—C12—C13—C17135.1 (2)
O3—C3—C4—C2927.5 (3)C15—O15—C14—C13100.6 (2)
C2—C3—C4—C29157.0 (2)C15—O15—C14—C8122.0 (3)
O3—C3—C4—C5151.9 (2)C18—C13—C14—C1594.1 (2)
C2—C3—C4—C532.5 (3)C12—C13—C14—C15141.4 (2)
O3—C3—C4—C2891.1 (3)C17—C13—C14—C1520.2 (3)
C2—C3—C4—C2884.4 (3)C18—C13—C14—O15157.5 (2)
C29—C4—C5—C667.1 (3)C12—C13—C14—O1578.0 (3)
C3—C4—C5—C6168.3 (2)C17—C13—C14—O1543.2 (2)
C28—C4—C5—C656.3 (3)C18—C13—C14—C867.6 (3)
C29—C4—C5—C10114.7 (2)C12—C13—C14—C856.9 (3)
C3—C4—C5—C109.9 (3)C17—C13—C14—C8178.1 (2)
C28—C4—C5—C10121.8 (2)C7—C8—C14—C1561.7 (3)
C4—C5—C6—O60.2 (4)C9—C8—C14—C15179.5 (3)
C10—C5—C6—O6177.9 (2)C30—C8—C14—C1553.2 (3)
C4—C5—C6—C7176.6 (2)C7—C8—C14—O15130.4 (2)
C10—C5—C6—C75.2 (4)C9—C8—C14—O15110.9 (2)
C5—C6—C7—O7177.8 (2)C30—C8—C14—O1515.4 (3)
O6—C6—C7—O70.7 (3)C7—C8—C14—C1396.0 (3)
C5—C6—C7—C83.5 (3)C9—C8—C14—C1322.7 (3)
O6—C6—C7—C8173.6 (2)C30—C8—C14—C13149.0 (2)
O7—C7—C8—C1434.2 (3)C14—O15—C15—C16100.9 (2)
C6—C7—C8—C14151.8 (2)C13—C14—C15—O15103.3 (2)
O7—C7—C8—C9152.6 (2)C8—C14—C15—O1597.3 (3)
C6—C7—C8—C933.3 (3)O15—C14—C15—C16104.3 (3)
O7—C7—C8—C3083.9 (3)C13—C14—C15—C161.0 (3)
C6—C7—C8—C3090.1 (2)C8—C14—C15—C16158.4 (3)
C7—C8—C9—C11164.3 (2)O15—C15—C16—C1742.6 (3)
C14—C8—C9—C1141.2 (3)C14—C15—C16—C1722.5 (3)
C30—C8—C9—C1180.5 (3)C15—C16—C17—C20161.3 (2)
C7—C8—C9—C1058.9 (3)C15—C16—C17—C1334.5 (3)
C14—C8—C9—C10178.05 (19)C14—C13—C17—C20160.2 (2)
C30—C8—C9—C1056.3 (3)C18—C13—C17—C2045.0 (3)
C2—C1—C10—C543.0 (3)C12—C13—C17—C2082.2 (3)
C2—C1—C10—C1976.4 (3)C14—C13—C17—C1633.5 (3)
C2—C1—C10—C9159.1 (3)C18—C13—C17—C1681.7 (3)
C6—C5—C10—C1133.6 (2)C12—C13—C17—C16151.1 (2)
C4—C5—C10—C144.6 (3)C16—C17—C20—C2225.6 (5)
C6—C5—C10—C19110.5 (3)C13—C17—C20—C2295.5 (4)
C4—C5—C10—C1971.3 (3)C16—C17—C20—C21153.1 (3)
C6—C5—C10—C917.7 (3)C13—C17—C20—C2185.8 (4)
C4—C5—C10—C9160.42 (19)C23—O23—C21—O21178.1 (4)
C11—C9—C10—C162.3 (3)C23—O23—C21—C201.4 (4)
C8—C9—C10—C1165.6 (2)C22—C20—C21—O21176.9 (4)
C11—C9—C10—C5177.0 (2)C17—C20—C21—O212.1 (6)
C8—C9—C10—C550.8 (3)C22—C20—C21—O232.5 (4)
C11—C9—C10—C1956.8 (3)C17—C20—C21—O23178.4 (2)
C8—C9—C10—C1975.4 (3)C21—C20—C22—C232.6 (4)
C10—C9—C11—C12150.8 (2)C17—C20—C22—C23178.5 (3)
C8—C9—C11—C1274.4 (3)C21—O23—C23—C220.1 (4)
C9—C11—C12—C1337.8 (3)C20—C22—C23—O231.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O70.822.182.624 (3)114
O6—H6···O3i0.822.152.897 (3)151
C2—H2···O21ii0.932.483.239 (4)139
C28—H28C···O7iii0.962.403.320 (4)162
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y+3/2, z.

Experimental details

Crystal data
Chemical formulaC26H30O6
Mr438.50
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)12.6858 (9), 13.1117 (9), 13.353 (1)
V3)2221.0 (3)
Z4
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.26 × 0.21 × 0.17
Data collection
DiffractometerBruker SMART APEX CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.974, 0.985
No. of measured, independent and
observed [I > 2σ(I)] reflections
14146, 2967, 2364
Rint0.035
(sin θ/λ)max1)0.660
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.125, 1.08
No. of reflections2967
No. of parameters290
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.24, 0.19

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996), SHELXL97 and PARST97 (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O6—H6···O70.822.182.624 (3)113.7
O6—H6···O3i0.822.152.897 (3)150.8
C2—H2···O21ii0.932.483.239 (4)139.0
C28—H28C···O7iii0.962.403.320 (4)161.6
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+1/2, y+1/2, z; (iii) x+1/2, y+3/2, z.
 

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