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The crystal structure of the title compound [4,17(20)-(cis)-pregna­diene-3,16-dione, C21H28O2] shows that the two mol­ecules in the asymmetric unit have similar conformations. The fused-ring system contains one sofa, two chairs and one envelope. Weak intermolecular C—H...O hydrogen bonds, together with van der Waals interactions, stabilize the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801003142/cf6049sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801003142/cf6049Isup2.hkl
Contains datablock I

CCDC reference: 159874

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.011 Å
  • R factor = 0.063
  • wR factor = 0.237
  • Data-to-parameter ratio = 8.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack -1.000 From the CIF: _refine_ls_abs_structure_Flack_su 4.000 Alert C Flack parameter is too small General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 3522 Count of symmetry unique reflns 3258 Completeness (_total/calc) 108.10% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 264 Fraction of Friedel pairs measured 0.081 Are heavy atom types Z>Si present no ALERT: MoKa measured Friedel data cannot be used to determine absolute structure in a light-atom study EXCEPT under VERY special conditions. It is preferred that Friedel data is merged in such cases.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

Guggulsterone E, an active constituent of an ayurvedic drug Guggulip derived from Commiphora mukul (Verma et al., 1998), possesses a significant choleterol and lipid-lowering activity. It has been marketed in India as a hypolipidaemic drug. In view of its potential medicinal importance, the present study of the title compound, (I), was undertaken to determine the conformation of its steroid nucleus.

The X-ray diffraction study of (I) shows that the asymmetric unit to contain two molecules of similar conformations and the structure of one molecule with the atomic numbering scheme is shown in Fig. 1. The molecule contains one fused-ring system (A/B/C/D) and five chiral centres. The torsion angles (Table 1) and least-squares-plane calculations indicate that, in both the molecules in the asymmetric unit, ring A is in a distorted sofa conformation, while rings B and C adopt a puckered and nearly a chair conformation, respectively. Ring D adopts an envelope conformation. The ring systems B/C and C/D are trans-fused with each other.

Based on literature precedence (Hill et al., 1991), the pregnane steroids have C10-substituents in a β-orientation. Accordingly, the methyl groups at C10 and C13 have β-axial orientation in both the molecules in the asymmetric unit. The shorter bond lengths C3—C4/C33—C34 1.453 (12)/1.428 (11) Å and C16—C17/C46—C47 1.470 (11)/1.500 (12) Å are indicativeof possible double-bond conjugation. The torsion angles C16—C17—C18—C19 - 174.5 (7)° and C46—C47—C48—C49 - 177.8 (7)° indicate that the title compound is the E-isomer of Guggulsterone. The crystal structure analysis reveals the presence of weak intermolecular C—H···O interactions (Table 2) which, along with the van der Waals forces, stabilize the solid-state structure.

Experimental top

Guggulsterone E was isolated by column chromatography of the ethyl acetate extract from Commiphora mukul following the available protocol (Patil et al., 1972). Diffraction-quality crystals were grown by slow evaporation of a methanol solution at room temperature.

Refinement top

All H atoms were placed in idealized positions geometrically and allowed to ride on their parent atoms. The present study does not establish the absolute configuration of the title molecule, but it is not known from other work. There are only 281 Friedel pairs, and the anomalous scattering effects are negligible.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXTL-NT (Bruker, 1997); program(s) used to refine structure: SHELXTL-NT; molecular graphics: NRCVAX (Gabe et al., 1989) and ORTEP (Johnson, 1965); software used to prepare material for publication: SHELXTL-NT.

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with labelling of the non-H atoms and displacement ellipsoids at the 50% probability level.
4,17 (20)-(cis)-pregnadiene-3,16-dione top
Crystal data top
C21H28O2Dx = 1.170 Mg m3
Mr = 312.44Melting point = 168–170 K
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 7.4634 (11) ÅCell parameters from 50 reflections
b = 13.747 (2) Åθ = 2.3–12.3°
c = 17.352 (3) ŵ = 0.07 mm1
β = 94.862 (12)°T = 293 K
V = 1773.8 (5) Å3Needle, colourless
Z = 40.35 × 0.25 × 0.20 mm
F(000) = 680
Data collection top
Bruker P4
diffractometer
Rint = 0.031
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.9°
Graphite monochromatorh = 18
θ–2θ scansk = 161
4388 measured reflectionsl = 2020
3522 independent reflections3 standard reflections every 97 reflections
2257 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.237 w = 1/[σ2(Fo2) + (0.1494P)2 + 1.4424P]
where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
3522 reflectionsΔρmax = 0.20 e Å3
421 parametersΔρmin = 0.20 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 1 (4)
Crystal data top
C21H28O2V = 1773.8 (5) Å3
Mr = 312.44Z = 4
Monoclinic, P21Mo Kα radiation
a = 7.4634 (11) ŵ = 0.07 mm1
b = 13.747 (2) ÅT = 293 K
c = 17.352 (3) Å0.35 × 0.25 × 0.20 mm
β = 94.862 (12)°
Data collection top
Bruker P4
diffractometer
Rint = 0.031
4388 measured reflections3 standard reflections every 97 reflections
3522 independent reflections intensity decay: none
2257 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.237Δρmax = 0.20 e Å3
S = 0.92Δρmin = 0.20 e Å3
3522 reflectionsAbsolute structure: Flack (1983)
421 parametersAbsolute structure parameter: 1 (4)
1 restraint
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
C10.1816 (10)0.7886 (6)0.7295 (4)0.0565 (18)
H1A0.08560.78950.68820.068*
H1B0.15410.73800.76560.068*
C20.1855 (11)0.8856 (6)0.7708 (4)0.063 (2)
H2A0.19020.93740.73310.075*
H2B0.07530.89320.79610.075*
C30.3441 (13)0.8951 (6)0.8304 (4)0.071 (2)
C40.5048 (11)0.8412 (7)0.8150 (5)0.068 (2)
H40.60470.84730.85050.081*
C50.5204 (8)0.7839 (6)0.7542 (4)0.0484 (16)
C60.6961 (10)0.7412 (7)0.7382 (5)0.072 (2)
H6A0.78000.74920.78360.086*
H6B0.74330.77670.69610.086*
C70.6847 (9)0.6335 (6)0.7172 (5)0.062 (2)
H7A0.65780.59620.76220.074*
H7B0.80000.61180.70170.074*
C80.5387 (8)0.6148 (5)0.6509 (4)0.0428 (16)
H80.56990.64940.60450.051*
C90.3583 (8)0.6532 (5)0.6749 (4)0.0391 (14)
H90.33520.61830.72230.047*
C100.3575 (8)0.7631 (5)0.6953 (4)0.0422 (15)
C110.2015 (8)0.6266 (5)0.6142 (4)0.0473 (17)
H11A0.08840.64390.63440.057*
H11B0.21240.66470.56770.057*
C120.1980 (8)0.5186 (5)0.5932 (4)0.0490 (17)
H12A0.17000.48100.63790.059*
H12B0.10340.50720.55230.059*
C130.3734 (8)0.4840 (5)0.5669 (4)0.0406 (15)
C140.5201 (7)0.5081 (5)0.6333 (4)0.0407 (15)
H140.47710.47890.67980.049*
C150.6806 (9)0.4463 (6)0.6148 (4)0.0559 (19)
H15A0.74870.47760.57650.067*
H15B0.75980.43330.66090.067*
C160.5906 (11)0.3540 (6)0.5832 (4)0.060 (2)
C170.4013 (10)0.3753 (5)0.5586 (4)0.0486 (17)
C180.2919 (12)0.3046 (6)0.5319 (4)0.061 (2)
H180.34040.24220.53440.073*
C190.1031 (13)0.3116 (7)0.4985 (5)0.087 (3)
H19A0.02380.30450.53900.130*
H19B0.07930.26110.46090.130*
H19C0.08380.37390.47420.130*
C200.3779 (13)0.8276 (6)0.6235 (4)0.075 (3)
H20A0.36890.89490.63750.112*
H20B0.28450.81210.58390.112*
H20C0.49310.81590.60440.112*
C210.4116 (11)0.5306 (6)0.4891 (4)0.061 (2)
H21A0.34170.49830.44770.091*
H21B0.53710.52430.48180.091*
H21C0.37980.59830.48940.091*
O10.3400 (11)0.9490 (6)0.8865 (4)0.113 (3)
O20.6718 (9)0.2766 (5)0.5802 (4)0.0865 (19)
C310.0048 (10)0.2322 (6)0.7183 (4)0.0568 (19)
H31A0.11650.24970.73960.068*
H31B0.02390.28360.68310.068*
C320.0335 (10)0.1371 (6)0.6725 (5)0.064 (2)
H32A0.07760.08710.70550.076*
H32B0.12280.14710.62920.076*
C330.1420 (12)0.1047 (6)0.6430 (5)0.066 (2)
C340.3048 (11)0.1251 (6)0.6894 (5)0.062 (2)
H340.41210.10110.67340.075*
C350.3106 (9)0.1770 (5)0.7550 (4)0.0525 (18)
C360.4773 (9)0.1844 (6)0.8060 (5)0.063 (2)
H36A0.57430.15500.78040.076*
H36B0.46320.14750.85270.076*
C370.5307 (9)0.2899 (7)0.8288 (4)0.060 (2)
H37A0.63530.28940.86600.072*
H37B0.56120.32550.78340.072*
C380.3728 (8)0.3396 (5)0.8641 (4)0.0475 (17)
H380.35150.30720.91280.057*
C390.1998 (8)0.3340 (5)0.8083 (4)0.0437 (16)
H390.22860.36630.76060.052*
C400.1453 (8)0.2271 (5)0.7848 (4)0.0442 (16)
C410.0478 (8)0.3928 (6)0.8385 (4)0.0532 (18)
H41A0.00880.36010.88370.064*
H41B0.05290.39300.79940.064*
C420.0940 (10)0.4989 (6)0.8605 (4)0.0550 (18)
H42A0.11640.53540.81450.066*
H42B0.00660.52870.88340.066*
C430.2589 (9)0.5017 (6)0.9174 (4)0.0493 (17)
C440.4137 (9)0.4481 (6)0.8801 (4)0.0532 (18)
H440.41850.47790.82900.064*
C450.5892 (10)0.4783 (7)0.9261 (5)0.064 (2)
H45A0.60940.44140.97370.076*
H45B0.69170.47060.89580.076*
C460.5524 (11)0.5838 (7)0.9419 (4)0.071 (2)
C470.3530 (11)0.6003 (6)0.9359 (4)0.059 (2)
C480.2849 (11)0.6891 (7)0.9477 (4)0.065 (2)
H480.36970.73810.95770.078*
C490.0969 (12)0.7203 (7)0.9472 (5)0.080 (3)
H49A0.05680.74500.89700.120*
H49B0.08730.77050.98520.120*
H49C0.02360.66590.95930.120*
C500.0823 (11)0.1704 (6)0.8531 (4)0.064 (2)
H50A0.04050.18680.85980.095*
H50B0.15640.18680.89920.095*
H50C0.09130.10190.84340.095*
C510.2240 (12)0.4579 (7)0.9977 (4)0.073 (2)
H51A0.13210.49481.01990.110*
H51B0.33280.46041.03140.110*
H51C0.18560.39150.99120.110*
O310.1349 (10)0.0565 (5)0.5829 (4)0.098 (2)
O320.6673 (8)0.6438 (6)0.9587 (4)0.093 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.061 (4)0.052 (4)0.057 (4)0.011 (4)0.008 (3)0.002 (4)
C20.076 (5)0.051 (5)0.063 (4)0.006 (4)0.022 (4)0.007 (4)
C30.111 (7)0.057 (5)0.044 (4)0.006 (5)0.002 (4)0.005 (4)
C40.063 (5)0.074 (6)0.065 (5)0.013 (5)0.003 (4)0.024 (4)
C50.044 (4)0.051 (4)0.049 (4)0.004 (3)0.002 (3)0.004 (3)
C60.052 (4)0.081 (6)0.082 (5)0.016 (4)0.001 (4)0.037 (5)
C70.045 (4)0.068 (5)0.072 (5)0.000 (4)0.003 (3)0.019 (4)
C80.029 (3)0.051 (4)0.049 (4)0.002 (3)0.006 (3)0.003 (3)
C90.039 (3)0.040 (4)0.038 (3)0.001 (3)0.001 (3)0.001 (3)
C100.044 (3)0.040 (4)0.044 (3)0.006 (3)0.007 (3)0.003 (3)
C110.032 (3)0.049 (4)0.061 (4)0.006 (3)0.006 (3)0.008 (4)
C120.038 (3)0.056 (4)0.053 (4)0.006 (3)0.002 (3)0.010 (3)
C130.039 (3)0.043 (4)0.038 (3)0.004 (3)0.003 (3)0.005 (3)
C140.028 (3)0.053 (4)0.041 (3)0.002 (3)0.000 (3)0.001 (3)
C150.042 (4)0.059 (5)0.065 (4)0.005 (4)0.003 (3)0.000 (4)
C160.078 (5)0.045 (5)0.057 (4)0.014 (4)0.007 (4)0.001 (4)
C170.066 (5)0.035 (4)0.046 (4)0.002 (4)0.015 (3)0.004 (3)
C180.082 (6)0.043 (4)0.061 (4)0.004 (4)0.020 (4)0.003 (4)
C190.108 (7)0.068 (6)0.085 (6)0.036 (6)0.011 (5)0.021 (5)
C200.126 (8)0.047 (5)0.054 (4)0.004 (5)0.026 (5)0.004 (4)
C210.085 (5)0.053 (5)0.044 (4)0.008 (4)0.010 (4)0.004 (3)
O10.154 (6)0.114 (6)0.067 (4)0.040 (5)0.008 (4)0.049 (4)
O20.104 (5)0.054 (4)0.100 (4)0.032 (4)0.005 (4)0.008 (3)
C310.056 (4)0.050 (4)0.064 (4)0.011 (4)0.003 (4)0.001 (4)
C320.056 (4)0.058 (5)0.072 (5)0.010 (4)0.020 (4)0.003 (4)
C330.082 (6)0.053 (5)0.062 (5)0.011 (4)0.002 (4)0.000 (4)
C340.065 (5)0.055 (5)0.067 (5)0.015 (4)0.008 (4)0.004 (4)
C350.047 (4)0.050 (4)0.060 (4)0.006 (3)0.002 (3)0.010 (4)
C360.044 (4)0.064 (5)0.081 (5)0.018 (4)0.001 (4)0.003 (4)
C370.038 (4)0.071 (5)0.071 (5)0.002 (4)0.001 (3)0.005 (4)
C380.034 (3)0.056 (4)0.052 (4)0.000 (3)0.002 (3)0.003 (3)
C390.034 (3)0.051 (4)0.045 (3)0.005 (3)0.003 (3)0.007 (3)
C400.037 (3)0.049 (4)0.046 (3)0.006 (3)0.005 (3)0.002 (3)
C410.033 (3)0.062 (5)0.063 (4)0.003 (3)0.005 (3)0.001 (4)
C420.054 (4)0.054 (5)0.057 (4)0.004 (4)0.004 (3)0.002 (4)
C430.050 (4)0.058 (5)0.040 (3)0.006 (4)0.005 (3)0.002 (3)
C440.048 (4)0.066 (5)0.046 (3)0.007 (4)0.006 (3)0.002 (4)
C450.048 (4)0.076 (6)0.068 (5)0.000 (4)0.012 (3)0.006 (4)
C460.073 (5)0.084 (7)0.055 (4)0.035 (5)0.007 (4)0.013 (4)
C470.070 (5)0.069 (6)0.039 (4)0.021 (4)0.009 (3)0.005 (4)
C480.070 (5)0.074 (6)0.051 (4)0.016 (5)0.010 (4)0.012 (4)
C490.093 (6)0.077 (7)0.074 (5)0.012 (6)0.036 (5)0.011 (5)
C500.066 (5)0.061 (5)0.064 (4)0.004 (4)0.007 (4)0.005 (4)
C510.085 (6)0.080 (6)0.058 (4)0.015 (5)0.025 (4)0.000 (4)
O310.128 (5)0.088 (5)0.075 (4)0.016 (4)0.009 (4)0.032 (4)
O320.079 (4)0.089 (5)0.107 (5)0.023 (4)0.015 (3)0.012 (4)
Geometric parameters (Å, º) top
C1—C21.513 (11)C31—C321.536 (11)
C1—C101.526 (9)C31—C401.540 (9)
C1—H1A0.970C31—H31A0.970
C1—H1B0.970C31—H31B0.970
C2—C31.510 (11)C32—C331.513 (11)
C2—H2A0.970C32—H32A0.970
C2—H2B0.970C32—H32B0.970
C3—O11.227 (9)C33—O311.233 (10)
C3—C41.453 (12)C33—C341.428 (11)
C4—C51.330 (10)C34—C351.340 (10)
C4—H40.930C34—H340.930
C5—C61.484 (10)C35—C361.468 (10)
C5—C101.546 (9)C35—C401.541 (9)
C6—C71.525 (12)C36—C371.546 (11)
C6—H6A0.970C36—H36A0.970
C6—H6B0.970C36—H36B0.970
C7—C81.537 (9)C37—C381.534 (9)
C7—H7A0.970C37—H37A0.970
C7—H7B0.970C37—H37B0.970
C8—C141.503 (10)C38—C441.542 (11)
C8—C91.536 (8)C38—C391.548 (9)
C8—H80.980C38—H380.980
C9—C111.551 (9)C39—C411.522 (10)
C9—C101.552 (9)C39—C401.570 (10)
C9—H90.980C39—H390.980
C10—C201.549 (10)C40—C501.526 (10)
C11—C121.530 (10)C41—C421.539 (11)
C11—H11A0.970C41—H41A0.970
C11—H11B0.970C41—H41B0.970
C12—C131.499 (9)C42—C431.511 (10)
C12—H12A0.970C42—H42A0.970
C12—H12B0.970C42—H42B0.970
C13—C171.517 (10)C43—C471.548 (11)
C13—C211.543 (9)C43—C441.557 (10)
C13—C141.556 (8)C43—C511.560 (10)
C14—C151.524 (10)C44—C451.532 (10)
C14—H140.980C44—H440.980
C15—C161.518 (11)C45—C461.506 (13)
C15—H15A0.970C45—H45A0.970
C15—H15B0.970C45—H45B0.970
C16—O21.228 (9)C46—O321.207 (10)
C16—C171.470 (11)C46—C471.500 (12)
C17—C181.328 (10)C47—C481.345 (12)
C18—C191.480 (12)C48—C491.466 (12)
C18—H180.930C48—H480.930
C19—H19A0.960C49—H49A0.960
C19—H19B0.960C49—H49B0.960
C19—H19C0.960C49—H49C0.960
C20—H20A0.960C50—H50A0.960
C20—H20B0.960C50—H50B0.960
C20—H20C0.960C50—H50C0.960
C21—H21A0.960C51—H51A0.960
C21—H21B0.960C51—H51B0.960
C21—H21C0.960C51—H51C0.960
C2—C1—C10113.8 (6)C32—C31—C40114.2 (6)
C2—C1—H1A108.8C32—C31—H31A108.7
C10—C1—H1A108.8C40—C31—H31A108.7
C2—C1—H1B108.8C32—C31—H31B108.7
C10—C1—H1B108.8C40—C31—H31B108.7
H1A—C1—H1B107.7H31A—C31—H31B107.6
C3—C2—C1112.6 (7)C33—C32—C31109.8 (6)
C3—C2—H2A109.1C33—C32—H32A109.7
C1—C2—H2A109.1C31—C32—H32A109.7
C3—C2—H2B109.1C33—C32—H32B109.7
C1—C2—H2B109.1C31—C32—H32B109.7
H2A—C2—H2B107.8H32A—C32—H32B108.2
O1—C3—C4122.1 (8)O31—C33—C34123.8 (8)
O1—C3—C2121.7 (8)O31—C33—C32117.9 (8)
C4—C3—C2116.2 (6)C34—C33—C32118.1 (7)
C5—C4—C3125.3 (7)C35—C34—C33123.3 (7)
C5—C4—H4117.4C35—C34—H34118.4
C3—C4—H4117.4C33—C34—H34118.4
C4—C5—C6121.4 (6)C34—C35—C36120.9 (7)
C4—C5—C10121.1 (6)C34—C35—C40123.7 (6)
C6—C5—C10117.5 (6)C36—C35—C40115.3 (6)
C5—C6—C7113.3 (6)C35—C36—C37114.0 (6)
C5—C6—H6A108.9C35—C36—H36A108.8
C7—C6—H6A108.9C37—C36—H36A108.8
C5—C6—H6B108.9C35—C36—H36B108.8
C7—C6—H6B108.9C37—C36—H36B108.8
H6A—C6—H6B107.7H36A—C36—H36B107.6
C6—C7—C8111.3 (7)C38—C37—C36109.2 (6)
C6—C7—H7A109.4C38—C37—H37A109.8
C8—C7—H7A109.4C36—C37—H37A109.8
C6—C7—H7B109.4C38—C37—H37B109.8
C8—C7—H7B109.4C36—C37—H37B109.8
H7A—C7—H7B108.0H37A—C37—H37B108.3
C14—C8—C9108.8 (5)C37—C38—C44110.8 (6)
C14—C8—C7111.3 (6)C37—C38—C39110.9 (6)
C9—C8—C7108.8 (5)C44—C38—C39107.6 (5)
C14—C8—H8109.3C37—C38—H38109.1
C9—C8—H8109.3C44—C38—H38109.1
C7—C8—H8109.3C39—C38—H38109.1
C8—C9—C11111.3 (5)C41—C39—C38111.4 (5)
C8—C9—C10114.6 (5)C41—C39—C40113.7 (5)
C11—C9—C10111.5 (5)C38—C39—C40113.1 (5)
C8—C9—H9106.2C41—C39—H39105.9
C11—C9—H9106.2C38—C39—H39105.9
C10—C9—H9106.2C40—C39—H39105.9
C1—C10—C5110.8 (5)C50—C40—C31110.6 (6)
C1—C10—C20109.1 (6)C50—C40—C35109.9 (6)
C5—C10—C20107.5 (6)C31—C40—C35108.7 (5)
C1—C10—C9109.4 (6)C50—C40—C39111.5 (6)
C5—C10—C9108.2 (5)C31—C40—C39107.9 (5)
C20—C10—C9111.8 (5)C35—C40—C39108.0 (6)
C12—C11—C9112.8 (5)C39—C41—C42115.5 (6)
C12—C11—H11A109.0C39—C41—H41A108.4
C9—C11—H11A109.0C42—C41—H41A108.4
C12—C11—H11B109.0C39—C41—H41B108.4
C9—C11—H11B109.0C42—C41—H41B108.4
H11A—C11—H11B107.8H41A—C41—H41B107.5
C13—C12—C11112.5 (6)C43—C42—C41109.8 (6)
C13—C12—H12A109.1C43—C42—H42A109.7
C11—C12—H12A109.1C41—C42—H42A109.7
C13—C12—H12B109.1C43—C42—H42B109.7
C11—C12—H12B109.1C41—C42—H42B109.7
H12A—C12—H12B107.8H42A—C42—H42B108.2
C12—C13—C17118.1 (6)C42—C43—C47119.2 (7)
C12—C13—C21111.4 (6)C42—C43—C44108.0 (6)
C17—C13—C21106.8 (6)C47—C43—C4499.3 (6)
C12—C13—C14106.6 (5)C42—C43—C51112.7 (6)
C17—C13—C14100.8 (5)C47—C43—C51105.1 (6)
C21—C13—C14112.9 (5)C44—C43—C51112.0 (7)
C8—C14—C15121.7 (6)C45—C44—C38120.2 (6)
C8—C14—C13113.9 (5)C45—C44—C43106.7 (6)
C15—C14—C13104.0 (5)C38—C44—C43112.9 (6)
C8—C14—H14105.3C45—C44—H44105.3
C15—C14—H14105.3C38—C44—H44105.3
C13—C14—H14105.3C43—C44—H44105.3
C16—C15—C14102.1 (6)C46—C45—C44101.3 (7)
C16—C15—H15A111.3C46—C45—H45A111.5
C14—C15—H15A111.3C44—C45—H45A111.5
C16—C15—H15B111.3C46—C45—H45B111.5
C14—C15—H15B111.3C44—C45—H45B111.5
H15A—C15—H15B109.2H45A—C45—H45B109.3
O2—C16—C17128.8 (8)O32—C46—C47126.4 (9)
O2—C16—C15122.4 (7)O32—C46—C45124.4 (8)
C17—C16—C15108.9 (6)C47—C46—C45109.1 (7)
C18—C17—C16120.2 (7)C48—C47—C46120.8 (7)
C18—C17—C13132.0 (7)C48—C47—C43131.0 (7)
C16—C17—C13107.7 (6)C46—C47—C43108.2 (7)
C17—C18—C19128.7 (8)C47—C48—C49129.7 (8)
C17—C18—H18115.7C47—C48—H48115.1
C19—C18—H18115.7C49—C48—H48115.1
C18—C19—H19A109.5C48—C49—H49A109.5
C18—C19—H19B109.5C48—C49—H49B109.5
H19A—C19—H19B109.5H49A—C49—H49B109.5
C18—C19—H19C109.5C48—C49—H49C109.5
H19A—C19—H19C109.5H49A—C49—H49C109.5
H19B—C19—H19C109.5H49B—C49—H49C109.5
C10—C20—H20A109.5C40—C50—H50A109.5
C10—C20—H20B109.5C40—C50—H50B109.5
H20A—C20—H20B109.5H50A—C50—H50B109.5
C10—C20—H20C109.5C40—C50—H50C109.5
H20A—C20—H20C109.5H50A—C50—H50C109.5
H20B—C20—H20C109.5H50B—C50—H50C109.5
C13—C21—H21A109.5C43—C51—H51A109.5
C13—C21—H21B109.5C43—C51—H51B109.5
H21A—C21—H21B109.5H51A—C51—H51B109.5
C13—C21—H21C109.5C43—C51—H51C109.5
H21A—C21—H21C109.5H51A—C51—H51C109.5
H21B—C21—H21C109.5H51B—C51—H51C109.5
C10—C1—C2—C352.0 (8)O31—C33—C34—C35179.5 (9)
C1—C2—C3—O1154.1 (9)C32—C33—C34—C354.6 (12)
C1—C2—C3—C429.3 (10)C33—C34—C35—C36171.5 (8)
O1—C3—C4—C5177.9 (9)C33—C34—C35—C404.7 (12)
C2—C3—C4—C51.3 (13)C34—C35—C36—C37129.3 (8)
C3—C4—C5—C6172.5 (8)C40—C35—C36—C3754.2 (9)
C3—C4—C5—C104.6 (13)C35—C36—C37—C3854.4 (9)
C4—C5—C6—C7134.8 (8)C36—C37—C38—C44174.3 (6)
C10—C5—C6—C748.0 (10)C36—C37—C38—C3954.9 (8)
C5—C6—C7—C852.5 (9)C37—C38—C39—C41173.6 (6)
C6—C7—C8—C14176.7 (6)C44—C38—C39—C4152.2 (7)
C6—C7—C8—C956.8 (8)C37—C38—C39—C4056.8 (8)
C14—C8—C9—C1152.5 (7)C44—C38—C39—C40178.2 (6)
C7—C8—C9—C11173.9 (6)C32—C31—C40—C5075.4 (8)
C14—C8—C9—C10179.7 (5)C32—C31—C40—C3545.4 (8)
C7—C8—C9—C1058.3 (7)C32—C31—C40—C39162.4 (6)
C2—C1—C10—C545.3 (8)C34—C35—C40—C50105.4 (8)
C2—C1—C10—C2072.9 (8)C36—C35—C40—C5070.9 (8)
C2—C1—C10—C9164.5 (6)C34—C35—C40—C3115.8 (10)
C4—C5—C10—C117.5 (10)C36—C35—C40—C31167.8 (6)
C6—C5—C10—C1165.3 (7)C34—C35—C40—C39132.7 (7)
C4—C5—C10—C20101.7 (8)C36—C35—C40—C3950.9 (8)
C6—C5—C10—C2075.5 (8)C41—C39—C40—C5059.5 (7)
C4—C5—C10—C9137.4 (7)C38—C39—C40—C5068.9 (7)
C6—C5—C10—C945.3 (8)C41—C39—C40—C3162.2 (7)
C8—C9—C10—C1171.6 (5)C38—C39—C40—C31169.4 (5)
C11—C9—C10—C160.8 (7)C41—C39—C40—C35179.6 (5)
C8—C9—C10—C550.8 (7)C38—C39—C40—C3552.0 (7)
C11—C9—C10—C5178.4 (5)C38—C39—C41—C4252.1 (8)
C8—C9—C10—C2067.4 (8)C40—C39—C41—C42178.6 (6)
C11—C9—C10—C2060.2 (8)C39—C41—C42—C4354.2 (8)
C8—C9—C11—C1250.9 (8)C41—C42—C43—C47168.3 (6)
C10—C9—C11—C12179.7 (6)C41—C42—C43—C4456.2 (8)
C9—C11—C12—C1354.5 (8)C41—C42—C43—C5168.0 (8)
C11—C12—C13—C17168.8 (6)C37—C38—C44—C4551.6 (9)
C11—C12—C13—C2167.0 (8)C39—C38—C44—C45173.0 (6)
C11—C12—C13—C1456.5 (7)C37—C38—C44—C43179.0 (6)
C9—C8—C14—C15174.3 (6)C39—C38—C44—C4359.6 (7)
C7—C8—C14—C1554.5 (8)C42—C43—C44—C45163.0 (6)
C9—C8—C14—C1359.8 (7)C47—C43—C44—C4538.1 (7)
C7—C8—C14—C13179.7 (5)C51—C43—C44—C4572.4 (8)
C12—C13—C14—C861.4 (7)C42—C43—C44—C3862.8 (8)
C17—C13—C14—C8174.7 (5)C47—C43—C44—C38172.3 (6)
C21—C13—C14—C861.2 (7)C51—C43—C44—C3861.8 (8)
C12—C13—C14—C15163.9 (6)C38—C44—C45—C46168.2 (6)
C17—C13—C14—C1540.0 (6)C43—C44—C45—C4638.0 (8)
C21—C13—C14—C1573.5 (7)C44—C45—C46—O32159.7 (8)
C8—C14—C15—C16167.1 (6)C44—C45—C46—C4722.2 (8)
C13—C14—C15—C1636.8 (7)O32—C46—C47—C481.7 (13)
C14—C15—C16—O2160.5 (7)C45—C46—C47—C48179.8 (7)
C14—C15—C16—C1719.7 (8)O32—C46—C47—C43176.9 (8)
O2—C16—C17—C183.2 (12)C45—C46—C47—C431.2 (8)
C15—C16—C17—C18177.1 (6)C42—C43—C47—C4841.4 (11)
O2—C16—C17—C13174.2 (8)C44—C43—C47—C48158.1 (8)
C15—C16—C17—C135.6 (8)C51—C43—C47—C4886.0 (10)
C12—C13—C17—C1839.7 (11)C42—C43—C47—C46140.2 (6)
C21—C13—C17—C1886.7 (9)C44—C43—C47—C4623.5 (7)
C14—C13—C17—C18155.3 (7)C51—C43—C47—C4692.4 (7)
C12—C13—C17—C16143.3 (6)C46—C47—C48—C49177.8 (7)
C21—C13—C17—C1690.3 (7)C43—C47—C48—C490.4 (14)
C14—C13—C17—C1627.8 (6)C16—C17—C18—C19174.5 (7)
C16—C17—C18—C19174.5 (7)C46—C47—C48—C49177.8 (7)
C13—C17—C18—C192.1 (13)H9—C9—C8—H8178.0
C40—C31—C32—C3354.8 (9)H39—C39—C38—H38179.1
C31—C32—C33—O31151.6 (8)C21—C13—C14—H14176.0
C31—C32—C33—C3433.3 (10)C51—C43—C44—H44176.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21C···O2i0.962.753.625 (10)153
C21—H21B···O31i0.962.813.723 (10)159
C32—H32B···O2ii0.972.453.237 (10)138
C45—H45A···O1iii0.972.433.274 (11)146
C50—H50B···O32iii0.962.763.641 (10)153
C51—H51B···O1iii0.962.733.678 (12)172
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x1, y, z; (iii) x+1, y1/2, z+2.

Experimental details

Crystal data
Chemical formulaC21H28O2
Mr312.44
Crystal system, space groupMonoclinic, P21
Temperature (K)293
a, b, c (Å)7.4634 (11), 13.747 (2), 17.352 (3)
β (°) 94.862 (12)
V3)1773.8 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.35 × 0.25 × 0.20
Data collection
DiffractometerBruker P4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4388, 3522, 2257
Rint0.031
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.237, 0.92
No. of reflections3522
No. of parameters421
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.20, 0.20
Absolute structureFlack (1983)
Absolute structure parameter1 (4)

Computer programs: XSCANS (Siemens, 1996), XSCANS, SHELXTL-NT (Bruker, 1997), SHELXTL-NT, NRCVAX (Gabe et al., 1989) and ORTEP (Johnson, 1965).

Selected torsion angles (º) top
C10—C1—C2—C352.0 (8)C32—C33—C34—C354.6 (12)
C1—C2—C3—C429.3 (10)C33—C34—C35—C404.7 (12)
C2—C3—C4—C51.3 (13)C40—C35—C36—C3754.2 (9)
C3—C4—C5—C104.6 (13)C35—C36—C37—C3854.4 (9)
C10—C5—C6—C748.0 (10)C36—C37—C38—C3954.9 (8)
C5—C6—C7—C852.5 (9)C37—C38—C39—C4056.8 (8)
C6—C7—C8—C956.8 (8)C32—C31—C40—C5075.4 (8)
C7—C8—C9—C1058.3 (7)C32—C31—C40—C3545.4 (8)
C2—C1—C10—C545.3 (8)C34—C35—C40—C3115.8 (10)
C2—C1—C10—C2072.9 (8)C36—C35—C40—C3950.9 (8)
C4—C5—C10—C117.5 (10)C38—C39—C40—C3552.0 (7)
C6—C5—C10—C945.3 (8)C41—C42—C43—C5168.0 (8)
C8—C9—C10—C550.8 (7)C47—C43—C44—C4538.1 (7)
C11—C12—C13—C2167.0 (8)C43—C44—C45—C4638.0 (8)
C17—C13—C14—C1540.0 (6)C44—C45—C46—C4722.2 (8)
C13—C14—C15—C1636.8 (7)C45—C46—C47—C431.2 (8)
C14—C15—C16—C1719.7 (8)C44—C43—C47—C4623.5 (7)
C15—C16—C17—C135.6 (8)C46—C47—C48—C49177.8 (7)
C14—C13—C17—C1627.8 (6)H9—C9—C8—H8178.0
C16—C17—C18—C19174.5 (7)H39—C39—C38—H38179.1
C40—C31—C32—C3354.8 (9)C21—C13—C14—H14176.0
C31—C32—C33—C3433.3 (10)C51—C43—C44—H44176.1
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C21—H21C···O2i0.962.7453.625 (10)153
C21—H21B···O31i0.962.8133.723 (10)159
C32—H32B···O2ii0.972.4533.237 (10)138
C45—H45A···O1iii0.972.4253.274 (11)146
C50—H50B···O32iii0.962.7593.641 (10)153
C51—H51B···O1iii0.962.7253.678 (12)172
Symmetry codes: (i) x+1, y+1/2, z+1; (ii) x1, y, z; (iii) x+1, y1/2, z+2.
 

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