The crystal structure of the title compound [4,17(20)-(
cis)-pregnadiene-3,16-dione, C
21H
28O
2] 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
CCDC reference: 159874
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (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
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
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.
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.
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.
4,17 (20)-(
cis)-pregnadiene-3,16-dione
top
Crystal data top
C21H28O2 | Dx = 1.170 Mg m−3 |
Mr = 312.44 | Melting point = 168–170 K |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.4634 (11) Å | Cell parameters from 50 reflections |
b = 13.747 (2) Å | θ = 2.3–12.3° |
c = 17.352 (3) Å | µ = 0.07 mm−1 |
β = 94.862 (12)° | T = 293 K |
V = 1773.8 (5) Å3 | Needle, colourless |
Z = 4 | 0.35 × 0.25 × 0.20 mm |
F(000) = 680 | |
Data collection top
Bruker P4 diffractometer | Rint = 0.031 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.9° |
Graphite monochromator | h = −1→8 |
θ–2θ scans | k = −16→1 |
4388 measured reflections | l = −20→20 |
3522 independent reflections | 3 standard reflections every 97 reflections |
2257 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.063 | H-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 reflections | Δρmax = 0.20 e Å−3 |
421 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −1 (4) |
Crystal data top
C21H28O2 | V = 1773.8 (5) Å3 |
Mr = 312.44 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 7.4634 (11) Å | µ = 0.07 mm−1 |
b = 13.747 (2) Å | T = 293 K |
c = 17.352 (3) Å | 0.35 × 0.25 × 0.20 mm |
β = 94.862 (12)° | |
Data collection top
Bruker P4 diffractometer | Rint = 0.031 |
4388 measured reflections | 3 standard reflections every 97 reflections |
3522 independent reflections | intensity decay: none |
2257 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.063 | H-atom parameters constrained |
wR(F2) = 0.237 | Δρmax = 0.20 e Å−3 |
S = 0.92 | Δρmin = −0.20 e Å−3 |
3522 reflections | Absolute structure: Flack (1983) |
421 parameters | Absolute 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 | x | y | z | Uiso*/Ueq | |
C1 | 0.1816 (10) | 0.7886 (6) | 0.7295 (4) | 0.0565 (18) | |
H1A | 0.0856 | 0.7895 | 0.6882 | 0.068* | |
H1B | 0.1541 | 0.7380 | 0.7656 | 0.068* | |
C2 | 0.1855 (11) | 0.8856 (6) | 0.7708 (4) | 0.063 (2) | |
H2A | 0.1902 | 0.9374 | 0.7331 | 0.075* | |
H2B | 0.0753 | 0.8932 | 0.7961 | 0.075* | |
C3 | 0.3441 (13) | 0.8951 (6) | 0.8304 (4) | 0.071 (2) | |
C4 | 0.5048 (11) | 0.8412 (7) | 0.8150 (5) | 0.068 (2) | |
H4 | 0.6047 | 0.8473 | 0.8505 | 0.081* | |
C5 | 0.5204 (8) | 0.7839 (6) | 0.7542 (4) | 0.0484 (16) | |
C6 | 0.6961 (10) | 0.7412 (7) | 0.7382 (5) | 0.072 (2) | |
H6A | 0.7800 | 0.7492 | 0.7836 | 0.086* | |
H6B | 0.7433 | 0.7767 | 0.6961 | 0.086* | |
C7 | 0.6847 (9) | 0.6335 (6) | 0.7172 (5) | 0.062 (2) | |
H7A | 0.6578 | 0.5962 | 0.7622 | 0.074* | |
H7B | 0.8000 | 0.6118 | 0.7017 | 0.074* | |
C8 | 0.5387 (8) | 0.6148 (5) | 0.6509 (4) | 0.0428 (16) | |
H8 | 0.5699 | 0.6494 | 0.6045 | 0.051* | |
C9 | 0.3583 (8) | 0.6532 (5) | 0.6749 (4) | 0.0391 (14) | |
H9 | 0.3352 | 0.6183 | 0.7223 | 0.047* | |
C10 | 0.3575 (8) | 0.7631 (5) | 0.6953 (4) | 0.0422 (15) | |
C11 | 0.2015 (8) | 0.6266 (5) | 0.6142 (4) | 0.0473 (17) | |
H11A | 0.0884 | 0.6439 | 0.6344 | 0.057* | |
H11B | 0.2124 | 0.6647 | 0.5677 | 0.057* | |
C12 | 0.1980 (8) | 0.5186 (5) | 0.5932 (4) | 0.0490 (17) | |
H12A | 0.1700 | 0.4810 | 0.6379 | 0.059* | |
H12B | 0.1034 | 0.5072 | 0.5523 | 0.059* | |
C13 | 0.3734 (8) | 0.4840 (5) | 0.5669 (4) | 0.0406 (15) | |
C14 | 0.5201 (7) | 0.5081 (5) | 0.6333 (4) | 0.0407 (15) | |
H14 | 0.4771 | 0.4789 | 0.6798 | 0.049* | |
C15 | 0.6806 (9) | 0.4463 (6) | 0.6148 (4) | 0.0559 (19) | |
H15A | 0.7487 | 0.4776 | 0.5765 | 0.067* | |
H15B | 0.7598 | 0.4333 | 0.6609 | 0.067* | |
C16 | 0.5906 (11) | 0.3540 (6) | 0.5832 (4) | 0.060 (2) | |
C17 | 0.4013 (10) | 0.3753 (5) | 0.5586 (4) | 0.0486 (17) | |
C18 | 0.2919 (12) | 0.3046 (6) | 0.5319 (4) | 0.061 (2) | |
H18 | 0.3404 | 0.2422 | 0.5344 | 0.073* | |
C19 | 0.1031 (13) | 0.3116 (7) | 0.4985 (5) | 0.087 (3) | |
H19A | 0.0238 | 0.3045 | 0.5390 | 0.130* | |
H19B | 0.0793 | 0.2611 | 0.4609 | 0.130* | |
H19C | 0.0838 | 0.3739 | 0.4742 | 0.130* | |
C20 | 0.3779 (13) | 0.8276 (6) | 0.6235 (4) | 0.075 (3) | |
H20A | 0.3689 | 0.8949 | 0.6375 | 0.112* | |
H20B | 0.2845 | 0.8121 | 0.5839 | 0.112* | |
H20C | 0.4931 | 0.8159 | 0.6044 | 0.112* | |
C21 | 0.4116 (11) | 0.5306 (6) | 0.4891 (4) | 0.061 (2) | |
H21A | 0.3417 | 0.4983 | 0.4477 | 0.091* | |
H21B | 0.5371 | 0.5243 | 0.4818 | 0.091* | |
H21C | 0.3798 | 0.5983 | 0.4894 | 0.091* | |
O1 | 0.3400 (11) | 0.9490 (6) | 0.8865 (4) | 0.113 (3) | |
O2 | 0.6718 (9) | 0.2766 (5) | 0.5802 (4) | 0.0865 (19) | |
C31 | −0.0048 (10) | 0.2322 (6) | 0.7183 (4) | 0.0568 (19) | |
H31A | −0.1165 | 0.2497 | 0.7396 | 0.068* | |
H31B | 0.0239 | 0.2836 | 0.6831 | 0.068* | |
C32 | −0.0335 (10) | 0.1371 (6) | 0.6725 (5) | 0.064 (2) | |
H32A | −0.0776 | 0.0871 | 0.7055 | 0.076* | |
H32B | −0.1228 | 0.1471 | 0.6292 | 0.076* | |
C33 | 0.1420 (12) | 0.1047 (6) | 0.6430 (5) | 0.066 (2) | |
C34 | 0.3048 (11) | 0.1251 (6) | 0.6894 (5) | 0.062 (2) | |
H34 | 0.4121 | 0.1011 | 0.6734 | 0.075* | |
C35 | 0.3106 (9) | 0.1770 (5) | 0.7550 (4) | 0.0525 (18) | |
C36 | 0.4773 (9) | 0.1844 (6) | 0.8060 (5) | 0.063 (2) | |
H36A | 0.5743 | 0.1550 | 0.7804 | 0.076* | |
H36B | 0.4632 | 0.1475 | 0.8527 | 0.076* | |
C37 | 0.5307 (9) | 0.2899 (7) | 0.8288 (4) | 0.060 (2) | |
H37A | 0.6353 | 0.2894 | 0.8660 | 0.072* | |
H37B | 0.5612 | 0.3255 | 0.7834 | 0.072* | |
C38 | 0.3728 (8) | 0.3396 (5) | 0.8641 (4) | 0.0475 (17) | |
H38 | 0.3515 | 0.3072 | 0.9128 | 0.057* | |
C39 | 0.1998 (8) | 0.3340 (5) | 0.8083 (4) | 0.0437 (16) | |
H39 | 0.2286 | 0.3663 | 0.7606 | 0.052* | |
C40 | 0.1453 (8) | 0.2271 (5) | 0.7848 (4) | 0.0442 (16) | |
C41 | 0.0478 (8) | 0.3928 (6) | 0.8385 (4) | 0.0532 (18) | |
H41A | 0.0088 | 0.3601 | 0.8837 | 0.064* | |
H41B | −0.0529 | 0.3930 | 0.7994 | 0.064* | |
C42 | 0.0940 (10) | 0.4989 (6) | 0.8605 (4) | 0.0550 (18) | |
H42A | 0.1164 | 0.5354 | 0.8145 | 0.066* | |
H42B | −0.0066 | 0.5287 | 0.8834 | 0.066* | |
C43 | 0.2589 (9) | 0.5017 (6) | 0.9174 (4) | 0.0493 (17) | |
C44 | 0.4137 (9) | 0.4481 (6) | 0.8801 (4) | 0.0532 (18) | |
H44 | 0.4185 | 0.4779 | 0.8290 | 0.064* | |
C45 | 0.5892 (10) | 0.4783 (7) | 0.9261 (5) | 0.064 (2) | |
H45A | 0.6094 | 0.4414 | 0.9737 | 0.076* | |
H45B | 0.6917 | 0.4706 | 0.8958 | 0.076* | |
C46 | 0.5524 (11) | 0.5838 (7) | 0.9419 (4) | 0.071 (2) | |
C47 | 0.3530 (11) | 0.6003 (6) | 0.9359 (4) | 0.059 (2) | |
C48 | 0.2849 (11) | 0.6891 (7) | 0.9477 (4) | 0.065 (2) | |
H48 | 0.3697 | 0.7381 | 0.9577 | 0.078* | |
C49 | 0.0969 (12) | 0.7203 (7) | 0.9472 (5) | 0.080 (3) | |
H49A | 0.0568 | 0.7450 | 0.8970 | 0.120* | |
H49B | 0.0873 | 0.7705 | 0.9852 | 0.120* | |
H49C | 0.0236 | 0.6659 | 0.9593 | 0.120* | |
C50 | 0.0823 (11) | 0.1704 (6) | 0.8531 (4) | 0.064 (2) | |
H50A | −0.0405 | 0.1868 | 0.8598 | 0.095* | |
H50B | 0.1564 | 0.1868 | 0.8992 | 0.095* | |
H50C | 0.0913 | 0.1019 | 0.8434 | 0.095* | |
C51 | 0.2240 (12) | 0.4579 (7) | 0.9977 (4) | 0.073 (2) | |
H51A | 0.1321 | 0.4948 | 1.0199 | 0.110* | |
H51B | 0.3328 | 0.4604 | 1.0314 | 0.110* | |
H51C | 0.1856 | 0.3915 | 0.9912 | 0.110* | |
O31 | 0.1349 (10) | 0.0565 (5) | 0.5829 (4) | 0.098 (2) | |
O32 | 0.6673 (8) | 0.6438 (6) | 0.9587 (4) | 0.093 (2) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.061 (4) | 0.052 (4) | 0.057 (4) | 0.011 (4) | 0.008 (3) | −0.002 (4) |
C2 | 0.076 (5) | 0.051 (5) | 0.063 (4) | 0.006 (4) | 0.022 (4) | −0.007 (4) |
C3 | 0.111 (7) | 0.057 (5) | 0.044 (4) | 0.006 (5) | −0.002 (4) | −0.005 (4) |
C4 | 0.063 (5) | 0.074 (6) | 0.065 (5) | −0.013 (5) | −0.003 (4) | −0.024 (4) |
C5 | 0.044 (4) | 0.051 (4) | 0.049 (4) | −0.004 (3) | −0.002 (3) | −0.004 (3) |
C6 | 0.052 (4) | 0.081 (6) | 0.082 (5) | −0.016 (4) | 0.001 (4) | −0.037 (5) |
C7 | 0.045 (4) | 0.068 (5) | 0.072 (5) | 0.000 (4) | 0.003 (3) | −0.019 (4) |
C8 | 0.029 (3) | 0.051 (4) | 0.049 (4) | −0.002 (3) | 0.006 (3) | −0.003 (3) |
C9 | 0.039 (3) | 0.040 (4) | 0.038 (3) | −0.001 (3) | −0.001 (3) | −0.001 (3) |
C10 | 0.044 (3) | 0.040 (4) | 0.044 (3) | 0.006 (3) | 0.007 (3) | −0.003 (3) |
C11 | 0.032 (3) | 0.049 (4) | 0.061 (4) | 0.006 (3) | 0.006 (3) | −0.008 (4) |
C12 | 0.038 (3) | 0.056 (4) | 0.053 (4) | −0.006 (3) | 0.002 (3) | −0.010 (3) |
C13 | 0.039 (3) | 0.043 (4) | 0.038 (3) | −0.004 (3) | −0.003 (3) | 0.005 (3) |
C14 | 0.028 (3) | 0.053 (4) | 0.041 (3) | −0.002 (3) | 0.000 (3) | −0.001 (3) |
C15 | 0.042 (4) | 0.059 (5) | 0.065 (4) | 0.005 (4) | −0.003 (3) | 0.000 (4) |
C16 | 0.078 (5) | 0.045 (5) | 0.057 (4) | 0.014 (4) | 0.007 (4) | −0.001 (4) |
C17 | 0.066 (5) | 0.035 (4) | 0.046 (4) | 0.002 (4) | 0.015 (3) | 0.004 (3) |
C18 | 0.082 (6) | 0.043 (4) | 0.061 (4) | −0.004 (4) | 0.020 (4) | −0.003 (4) |
C19 | 0.108 (7) | 0.068 (6) | 0.085 (6) | −0.036 (6) | 0.011 (5) | −0.021 (5) |
C20 | 0.126 (8) | 0.047 (5) | 0.054 (4) | −0.004 (5) | 0.026 (5) | 0.004 (4) |
C21 | 0.085 (5) | 0.053 (5) | 0.044 (4) | 0.008 (4) | 0.010 (4) | 0.004 (3) |
O1 | 0.154 (6) | 0.114 (6) | 0.067 (4) | 0.040 (5) | −0.008 (4) | −0.049 (4) |
O2 | 0.104 (5) | 0.054 (4) | 0.100 (4) | 0.032 (4) | −0.005 (4) | −0.008 (3) |
C31 | 0.056 (4) | 0.050 (4) | 0.064 (4) | 0.011 (4) | 0.003 (4) | −0.001 (4) |
C32 | 0.056 (4) | 0.058 (5) | 0.072 (5) | −0.010 (4) | −0.020 (4) | −0.003 (4) |
C33 | 0.082 (6) | 0.053 (5) | 0.062 (5) | 0.011 (4) | 0.002 (4) | 0.000 (4) |
C34 | 0.065 (5) | 0.055 (5) | 0.067 (5) | 0.015 (4) | 0.008 (4) | 0.004 (4) |
C35 | 0.047 (4) | 0.050 (4) | 0.060 (4) | 0.006 (3) | −0.002 (3) | 0.010 (4) |
C36 | 0.044 (4) | 0.064 (5) | 0.081 (5) | 0.018 (4) | 0.001 (4) | −0.003 (4) |
C37 | 0.038 (4) | 0.071 (5) | 0.071 (5) | 0.002 (4) | −0.001 (3) | 0.005 (4) |
C38 | 0.034 (3) | 0.056 (4) | 0.052 (4) | 0.000 (3) | 0.002 (3) | 0.003 (3) |
C39 | 0.034 (3) | 0.051 (4) | 0.045 (3) | 0.005 (3) | −0.003 (3) | 0.007 (3) |
C40 | 0.037 (3) | 0.049 (4) | 0.046 (3) | 0.006 (3) | −0.005 (3) | 0.002 (3) |
C41 | 0.033 (3) | 0.062 (5) | 0.063 (4) | −0.003 (3) | −0.005 (3) | −0.001 (4) |
C42 | 0.054 (4) | 0.054 (5) | 0.057 (4) | 0.004 (4) | 0.004 (3) | 0.002 (4) |
C43 | 0.050 (4) | 0.058 (5) | 0.040 (3) | −0.006 (4) | 0.005 (3) | −0.002 (3) |
C44 | 0.048 (4) | 0.066 (5) | 0.046 (3) | −0.007 (4) | 0.006 (3) | 0.002 (4) |
C45 | 0.048 (4) | 0.076 (6) | 0.068 (5) | 0.000 (4) | 0.012 (3) | −0.006 (4) |
C46 | 0.073 (5) | 0.084 (7) | 0.055 (4) | −0.035 (5) | 0.007 (4) | −0.013 (4) |
C47 | 0.070 (5) | 0.069 (6) | 0.039 (4) | −0.021 (4) | 0.009 (3) | −0.005 (4) |
C48 | 0.070 (5) | 0.074 (6) | 0.051 (4) | −0.016 (5) | 0.010 (4) | −0.012 (4) |
C49 | 0.093 (6) | 0.077 (7) | 0.074 (5) | −0.012 (6) | 0.036 (5) | −0.011 (5) |
C50 | 0.066 (5) | 0.061 (5) | 0.064 (4) | −0.004 (4) | 0.007 (4) | 0.005 (4) |
C51 | 0.085 (6) | 0.080 (6) | 0.058 (4) | −0.015 (5) | 0.025 (4) | 0.000 (4) |
O31 | 0.128 (5) | 0.088 (5) | 0.075 (4) | 0.016 (4) | −0.009 (4) | −0.032 (4) |
O32 | 0.079 (4) | 0.089 (5) | 0.107 (5) | −0.023 (4) | −0.015 (3) | −0.012 (4) |
Geometric parameters (Å, º) top
C1—C2 | 1.513 (11) | C31—C32 | 1.536 (11) |
C1—C10 | 1.526 (9) | C31—C40 | 1.540 (9) |
C1—H1A | 0.970 | C31—H31A | 0.970 |
C1—H1B | 0.970 | C31—H31B | 0.970 |
C2—C3 | 1.510 (11) | C32—C33 | 1.513 (11) |
C2—H2A | 0.970 | C32—H32A | 0.970 |
C2—H2B | 0.970 | C32—H32B | 0.970 |
C3—O1 | 1.227 (9) | C33—O31 | 1.233 (10) |
C3—C4 | 1.453 (12) | C33—C34 | 1.428 (11) |
C4—C5 | 1.330 (10) | C34—C35 | 1.340 (10) |
C4—H4 | 0.930 | C34—H34 | 0.930 |
C5—C6 | 1.484 (10) | C35—C36 | 1.468 (10) |
C5—C10 | 1.546 (9) | C35—C40 | 1.541 (9) |
C6—C7 | 1.525 (12) | C36—C37 | 1.546 (11) |
C6—H6A | 0.970 | C36—H36A | 0.970 |
C6—H6B | 0.970 | C36—H36B | 0.970 |
C7—C8 | 1.537 (9) | C37—C38 | 1.534 (9) |
C7—H7A | 0.970 | C37—H37A | 0.970 |
C7—H7B | 0.970 | C37—H37B | 0.970 |
C8—C14 | 1.503 (10) | C38—C44 | 1.542 (11) |
C8—C9 | 1.536 (8) | C38—C39 | 1.548 (9) |
C8—H8 | 0.980 | C38—H38 | 0.980 |
C9—C11 | 1.551 (9) | C39—C41 | 1.522 (10) |
C9—C10 | 1.552 (9) | C39—C40 | 1.570 (10) |
C9—H9 | 0.980 | C39—H39 | 0.980 |
C10—C20 | 1.549 (10) | C40—C50 | 1.526 (10) |
C11—C12 | 1.530 (10) | C41—C42 | 1.539 (11) |
C11—H11A | 0.970 | C41—H41A | 0.970 |
C11—H11B | 0.970 | C41—H41B | 0.970 |
C12—C13 | 1.499 (9) | C42—C43 | 1.511 (10) |
C12—H12A | 0.970 | C42—H42A | 0.970 |
C12—H12B | 0.970 | C42—H42B | 0.970 |
C13—C17 | 1.517 (10) | C43—C47 | 1.548 (11) |
C13—C21 | 1.543 (9) | C43—C44 | 1.557 (10) |
C13—C14 | 1.556 (8) | C43—C51 | 1.560 (10) |
C14—C15 | 1.524 (10) | C44—C45 | 1.532 (10) |
C14—H14 | 0.980 | C44—H44 | 0.980 |
C15—C16 | 1.518 (11) | C45—C46 | 1.506 (13) |
C15—H15A | 0.970 | C45—H45A | 0.970 |
C15—H15B | 0.970 | C45—H45B | 0.970 |
C16—O2 | 1.228 (9) | C46—O32 | 1.207 (10) |
C16—C17 | 1.470 (11) | C46—C47 | 1.500 (12) |
C17—C18 | 1.328 (10) | C47—C48 | 1.345 (12) |
C18—C19 | 1.480 (12) | C48—C49 | 1.466 (12) |
C18—H18 | 0.930 | C48—H48 | 0.930 |
C19—H19A | 0.960 | C49—H49A | 0.960 |
C19—H19B | 0.960 | C49—H49B | 0.960 |
C19—H19C | 0.960 | C49—H49C | 0.960 |
C20—H20A | 0.960 | C50—H50A | 0.960 |
C20—H20B | 0.960 | C50—H50B | 0.960 |
C20—H20C | 0.960 | C50—H50C | 0.960 |
C21—H21A | 0.960 | C51—H51A | 0.960 |
C21—H21B | 0.960 | C51—H51B | 0.960 |
C21—H21C | 0.960 | C51—H51C | 0.960 |
| | | |
C2—C1—C10 | 113.8 (6) | C32—C31—C40 | 114.2 (6) |
C2—C1—H1A | 108.8 | C32—C31—H31A | 108.7 |
C10—C1—H1A | 108.8 | C40—C31—H31A | 108.7 |
C2—C1—H1B | 108.8 | C32—C31—H31B | 108.7 |
C10—C1—H1B | 108.8 | C40—C31—H31B | 108.7 |
H1A—C1—H1B | 107.7 | H31A—C31—H31B | 107.6 |
C3—C2—C1 | 112.6 (7) | C33—C32—C31 | 109.8 (6) |
C3—C2—H2A | 109.1 | C33—C32—H32A | 109.7 |
C1—C2—H2A | 109.1 | C31—C32—H32A | 109.7 |
C3—C2—H2B | 109.1 | C33—C32—H32B | 109.7 |
C1—C2—H2B | 109.1 | C31—C32—H32B | 109.7 |
H2A—C2—H2B | 107.8 | H32A—C32—H32B | 108.2 |
O1—C3—C4 | 122.1 (8) | O31—C33—C34 | 123.8 (8) |
O1—C3—C2 | 121.7 (8) | O31—C33—C32 | 117.9 (8) |
C4—C3—C2 | 116.2 (6) | C34—C33—C32 | 118.1 (7) |
C5—C4—C3 | 125.3 (7) | C35—C34—C33 | 123.3 (7) |
C5—C4—H4 | 117.4 | C35—C34—H34 | 118.4 |
C3—C4—H4 | 117.4 | C33—C34—H34 | 118.4 |
C4—C5—C6 | 121.4 (6) | C34—C35—C36 | 120.9 (7) |
C4—C5—C10 | 121.1 (6) | C34—C35—C40 | 123.7 (6) |
C6—C5—C10 | 117.5 (6) | C36—C35—C40 | 115.3 (6) |
C5—C6—C7 | 113.3 (6) | C35—C36—C37 | 114.0 (6) |
C5—C6—H6A | 108.9 | C35—C36—H36A | 108.8 |
C7—C6—H6A | 108.9 | C37—C36—H36A | 108.8 |
C5—C6—H6B | 108.9 | C35—C36—H36B | 108.8 |
C7—C6—H6B | 108.9 | C37—C36—H36B | 108.8 |
H6A—C6—H6B | 107.7 | H36A—C36—H36B | 107.6 |
C6—C7—C8 | 111.3 (7) | C38—C37—C36 | 109.2 (6) |
C6—C7—H7A | 109.4 | C38—C37—H37A | 109.8 |
C8—C7—H7A | 109.4 | C36—C37—H37A | 109.8 |
C6—C7—H7B | 109.4 | C38—C37—H37B | 109.8 |
C8—C7—H7B | 109.4 | C36—C37—H37B | 109.8 |
H7A—C7—H7B | 108.0 | H37A—C37—H37B | 108.3 |
C14—C8—C9 | 108.8 (5) | C37—C38—C44 | 110.8 (6) |
C14—C8—C7 | 111.3 (6) | C37—C38—C39 | 110.9 (6) |
C9—C8—C7 | 108.8 (5) | C44—C38—C39 | 107.6 (5) |
C14—C8—H8 | 109.3 | C37—C38—H38 | 109.1 |
C9—C8—H8 | 109.3 | C44—C38—H38 | 109.1 |
C7—C8—H8 | 109.3 | C39—C38—H38 | 109.1 |
C8—C9—C11 | 111.3 (5) | C41—C39—C38 | 111.4 (5) |
C8—C9—C10 | 114.6 (5) | C41—C39—C40 | 113.7 (5) |
C11—C9—C10 | 111.5 (5) | C38—C39—C40 | 113.1 (5) |
C8—C9—H9 | 106.2 | C41—C39—H39 | 105.9 |
C11—C9—H9 | 106.2 | C38—C39—H39 | 105.9 |
C10—C9—H9 | 106.2 | C40—C39—H39 | 105.9 |
C1—C10—C5 | 110.8 (5) | C50—C40—C31 | 110.6 (6) |
C1—C10—C20 | 109.1 (6) | C50—C40—C35 | 109.9 (6) |
C5—C10—C20 | 107.5 (6) | C31—C40—C35 | 108.7 (5) |
C1—C10—C9 | 109.4 (6) | C50—C40—C39 | 111.5 (6) |
C5—C10—C9 | 108.2 (5) | C31—C40—C39 | 107.9 (5) |
C20—C10—C9 | 111.8 (5) | C35—C40—C39 | 108.0 (6) |
C12—C11—C9 | 112.8 (5) | C39—C41—C42 | 115.5 (6) |
C12—C11—H11A | 109.0 | C39—C41—H41A | 108.4 |
C9—C11—H11A | 109.0 | C42—C41—H41A | 108.4 |
C12—C11—H11B | 109.0 | C39—C41—H41B | 108.4 |
C9—C11—H11B | 109.0 | C42—C41—H41B | 108.4 |
H11A—C11—H11B | 107.8 | H41A—C41—H41B | 107.5 |
C13—C12—C11 | 112.5 (6) | C43—C42—C41 | 109.8 (6) |
C13—C12—H12A | 109.1 | C43—C42—H42A | 109.7 |
C11—C12—H12A | 109.1 | C41—C42—H42A | 109.7 |
C13—C12—H12B | 109.1 | C43—C42—H42B | 109.7 |
C11—C12—H12B | 109.1 | C41—C42—H42B | 109.7 |
H12A—C12—H12B | 107.8 | H42A—C42—H42B | 108.2 |
C12—C13—C17 | 118.1 (6) | C42—C43—C47 | 119.2 (7) |
C12—C13—C21 | 111.4 (6) | C42—C43—C44 | 108.0 (6) |
C17—C13—C21 | 106.8 (6) | C47—C43—C44 | 99.3 (6) |
C12—C13—C14 | 106.6 (5) | C42—C43—C51 | 112.7 (6) |
C17—C13—C14 | 100.8 (5) | C47—C43—C51 | 105.1 (6) |
C21—C13—C14 | 112.9 (5) | C44—C43—C51 | 112.0 (7) |
C8—C14—C15 | 121.7 (6) | C45—C44—C38 | 120.2 (6) |
C8—C14—C13 | 113.9 (5) | C45—C44—C43 | 106.7 (6) |
C15—C14—C13 | 104.0 (5) | C38—C44—C43 | 112.9 (6) |
C8—C14—H14 | 105.3 | C45—C44—H44 | 105.3 |
C15—C14—H14 | 105.3 | C38—C44—H44 | 105.3 |
C13—C14—H14 | 105.3 | C43—C44—H44 | 105.3 |
C16—C15—C14 | 102.1 (6) | C46—C45—C44 | 101.3 (7) |
C16—C15—H15A | 111.3 | C46—C45—H45A | 111.5 |
C14—C15—H15A | 111.3 | C44—C45—H45A | 111.5 |
C16—C15—H15B | 111.3 | C46—C45—H45B | 111.5 |
C14—C15—H15B | 111.3 | C44—C45—H45B | 111.5 |
H15A—C15—H15B | 109.2 | H45A—C45—H45B | 109.3 |
O2—C16—C17 | 128.8 (8) | O32—C46—C47 | 126.4 (9) |
O2—C16—C15 | 122.4 (7) | O32—C46—C45 | 124.4 (8) |
C17—C16—C15 | 108.9 (6) | C47—C46—C45 | 109.1 (7) |
C18—C17—C16 | 120.2 (7) | C48—C47—C46 | 120.8 (7) |
C18—C17—C13 | 132.0 (7) | C48—C47—C43 | 131.0 (7) |
C16—C17—C13 | 107.7 (6) | C46—C47—C43 | 108.2 (7) |
C17—C18—C19 | 128.7 (8) | C47—C48—C49 | 129.7 (8) |
C17—C18—H18 | 115.7 | C47—C48—H48 | 115.1 |
C19—C18—H18 | 115.7 | C49—C48—H48 | 115.1 |
C18—C19—H19A | 109.5 | C48—C49—H49A | 109.5 |
C18—C19—H19B | 109.5 | C48—C49—H49B | 109.5 |
H19A—C19—H19B | 109.5 | H49A—C49—H49B | 109.5 |
C18—C19—H19C | 109.5 | C48—C49—H49C | 109.5 |
H19A—C19—H19C | 109.5 | H49A—C49—H49C | 109.5 |
H19B—C19—H19C | 109.5 | H49B—C49—H49C | 109.5 |
C10—C20—H20A | 109.5 | C40—C50—H50A | 109.5 |
C10—C20—H20B | 109.5 | C40—C50—H50B | 109.5 |
H20A—C20—H20B | 109.5 | H50A—C50—H50B | 109.5 |
C10—C20—H20C | 109.5 | C40—C50—H50C | 109.5 |
H20A—C20—H20C | 109.5 | H50A—C50—H50C | 109.5 |
H20B—C20—H20C | 109.5 | H50B—C50—H50C | 109.5 |
C13—C21—H21A | 109.5 | C43—C51—H51A | 109.5 |
C13—C21—H21B | 109.5 | C43—C51—H51B | 109.5 |
H21A—C21—H21B | 109.5 | H51A—C51—H51B | 109.5 |
C13—C21—H21C | 109.5 | C43—C51—H51C | 109.5 |
H21A—C21—H21C | 109.5 | H51A—C51—H51C | 109.5 |
H21B—C21—H21C | 109.5 | H51B—C51—H51C | 109.5 |
| | | |
C10—C1—C2—C3 | −52.0 (8) | O31—C33—C34—C35 | −179.5 (9) |
C1—C2—C3—O1 | −154.1 (9) | C32—C33—C34—C35 | −4.6 (12) |
C1—C2—C3—C4 | 29.3 (10) | C33—C34—C35—C36 | 171.5 (8) |
O1—C3—C4—C5 | −177.9 (9) | C33—C34—C35—C40 | −4.7 (12) |
C2—C3—C4—C5 | −1.3 (13) | C34—C35—C36—C37 | 129.3 (8) |
C3—C4—C5—C6 | 172.5 (8) | C40—C35—C36—C37 | −54.2 (9) |
C3—C4—C5—C10 | −4.6 (13) | C35—C36—C37—C38 | 54.4 (9) |
C4—C5—C6—C7 | 134.8 (8) | C36—C37—C38—C44 | −174.3 (6) |
C10—C5—C6—C7 | −48.0 (10) | C36—C37—C38—C39 | −54.9 (8) |
C5—C6—C7—C8 | 52.5 (9) | C37—C38—C39—C41 | −173.6 (6) |
C6—C7—C8—C14 | −176.7 (6) | C44—C38—C39—C41 | −52.2 (7) |
C6—C7—C8—C9 | −56.8 (8) | C37—C38—C39—C40 | 56.8 (8) |
C14—C8—C9—C11 | −52.5 (7) | C44—C38—C39—C40 | 178.2 (6) |
C7—C8—C9—C11 | −173.9 (6) | C32—C31—C40—C50 | −75.4 (8) |
C14—C8—C9—C10 | 179.7 (5) | C32—C31—C40—C35 | 45.4 (8) |
C7—C8—C9—C10 | 58.3 (7) | C32—C31—C40—C39 | 162.4 (6) |
C2—C1—C10—C5 | 45.3 (8) | C34—C35—C40—C50 | 105.4 (8) |
C2—C1—C10—C20 | −72.9 (8) | C36—C35—C40—C50 | −70.9 (8) |
C2—C1—C10—C9 | 164.5 (6) | C34—C35—C40—C31 | −15.8 (10) |
C4—C5—C10—C1 | −17.5 (10) | C36—C35—C40—C31 | 167.8 (6) |
C6—C5—C10—C1 | 165.3 (7) | C34—C35—C40—C39 | −132.7 (7) |
C4—C5—C10—C20 | 101.7 (8) | C36—C35—C40—C39 | 50.9 (8) |
C6—C5—C10—C20 | −75.5 (8) | C41—C39—C40—C50 | −59.5 (7) |
C4—C5—C10—C9 | −137.4 (7) | C38—C39—C40—C50 | 68.9 (7) |
C6—C5—C10—C9 | 45.3 (8) | C41—C39—C40—C31 | 62.2 (7) |
C8—C9—C10—C1 | −171.6 (5) | C38—C39—C40—C31 | −169.4 (5) |
C11—C9—C10—C1 | 60.8 (7) | C41—C39—C40—C35 | 179.6 (5) |
C8—C9—C10—C5 | −50.8 (7) | C38—C39—C40—C35 | −52.0 (7) |
C11—C9—C10—C5 | −178.4 (5) | C38—C39—C41—C42 | 52.1 (8) |
C8—C9—C10—C20 | 67.4 (8) | C40—C39—C41—C42 | −178.6 (6) |
C11—C9—C10—C20 | −60.2 (8) | C39—C41—C42—C43 | −54.2 (8) |
C8—C9—C11—C12 | 50.9 (8) | C41—C42—C43—C47 | 168.3 (6) |
C10—C9—C11—C12 | −179.7 (6) | C41—C42—C43—C44 | 56.2 (8) |
C9—C11—C12—C13 | −54.5 (8) | C41—C42—C43—C51 | −68.0 (8) |
C11—C12—C13—C17 | 168.8 (6) | C37—C38—C44—C45 | −51.6 (9) |
C11—C12—C13—C21 | −67.0 (8) | C39—C38—C44—C45 | −173.0 (6) |
C11—C12—C13—C14 | 56.5 (7) | C37—C38—C44—C43 | −179.0 (6) |
C9—C8—C14—C15 | −174.3 (6) | C39—C38—C44—C43 | 59.6 (7) |
C7—C8—C14—C15 | −54.5 (8) | C42—C43—C44—C45 | 163.0 (6) |
C9—C8—C14—C13 | 59.8 (7) | C47—C43—C44—C45 | 38.1 (7) |
C7—C8—C14—C13 | 179.7 (5) | C51—C43—C44—C45 | −72.4 (8) |
C12—C13—C14—C8 | −61.4 (7) | C42—C43—C44—C38 | −62.8 (8) |
C17—C13—C14—C8 | 174.7 (5) | C47—C43—C44—C38 | 172.3 (6) |
C21—C13—C14—C8 | 61.2 (7) | C51—C43—C44—C38 | 61.8 (8) |
C12—C13—C14—C15 | 163.9 (6) | C38—C44—C45—C46 | −168.2 (6) |
C17—C13—C14—C15 | 40.0 (6) | C43—C44—C45—C46 | −38.0 (8) |
C21—C13—C14—C15 | −73.5 (7) | C44—C45—C46—O32 | −159.7 (8) |
C8—C14—C15—C16 | −167.1 (6) | C44—C45—C46—C47 | 22.2 (8) |
C13—C14—C15—C16 | −36.8 (7) | O32—C46—C47—C48 | 1.7 (13) |
C14—C15—C16—O2 | −160.5 (7) | C45—C46—C47—C48 | 179.8 (7) |
C14—C15—C16—C17 | 19.7 (8) | O32—C46—C47—C43 | −176.9 (8) |
O2—C16—C17—C18 | 3.2 (12) | C45—C46—C47—C43 | 1.2 (8) |
C15—C16—C17—C18 | −177.1 (6) | C42—C43—C47—C48 | 41.4 (11) |
O2—C16—C17—C13 | −174.2 (8) | C44—C43—C47—C48 | 158.1 (8) |
C15—C16—C17—C13 | 5.6 (8) | C51—C43—C47—C48 | −86.0 (10) |
C12—C13—C17—C18 | 39.7 (11) | C42—C43—C47—C46 | −140.2 (6) |
C21—C13—C17—C18 | −86.7 (9) | C44—C43—C47—C46 | −23.5 (7) |
C14—C13—C17—C18 | 155.3 (7) | C51—C43—C47—C46 | 92.4 (7) |
C12—C13—C17—C16 | −143.3 (6) | C46—C47—C48—C49 | −177.8 (7) |
C21—C13—C17—C16 | 90.3 (7) | C43—C47—C48—C49 | 0.4 (14) |
C14—C13—C17—C16 | −27.8 (6) | C16—C17—C18—C19 | −174.5 (7) |
C16—C17—C18—C19 | −174.5 (7) | C46—C47—C48—C49 | −177.8 (7) |
C13—C17—C18—C19 | 2.1 (13) | H9—C9—C8—H8 | −178.0 |
C40—C31—C32—C33 | −54.8 (9) | H39—C39—C38—H38 | −179.1 |
C31—C32—C33—O31 | −151.6 (8) | C21—C13—C14—H14 | 176.0 |
C31—C32—C33—C34 | 33.3 (10) | C51—C43—C44—H44 | 176.1 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21C···O2i | 0.96 | 2.75 | 3.625 (10) | 153 |
C21—H21B···O31i | 0.96 | 2.81 | 3.723 (10) | 159 |
C32—H32B···O2ii | 0.97 | 2.45 | 3.237 (10) | 138 |
C45—H45A···O1iii | 0.97 | 2.43 | 3.274 (11) | 146 |
C50—H50B···O32iii | 0.96 | 2.76 | 3.641 (10) | 153 |
C51—H51B···O1iii | 0.96 | 2.73 | 3.678 (12) | 172 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+2. |
Experimental details
Crystal data |
Chemical formula | C21H28O2 |
Mr | 312.44 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 293 |
a, b, c (Å) | 7.4634 (11), 13.747 (2), 17.352 (3) |
β (°) | 94.862 (12) |
V (Å3) | 1773.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.35 × 0.25 × 0.20 |
|
Data collection |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4388, 3522, 2257 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.595 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.237, 0.92 |
No. of reflections | 3522 |
No. of parameters | 421 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.20 |
Absolute structure | Flack (1983) |
Absolute structure parameter | −1 (4) |
Selected torsion angles (º) topC10—C1—C2—C3 | −52.0 (8) | C32—C33—C34—C35 | −4.6 (12) |
C1—C2—C3—C4 | 29.3 (10) | C33—C34—C35—C40 | −4.7 (12) |
C2—C3—C4—C5 | −1.3 (13) | C40—C35—C36—C37 | −54.2 (9) |
C3—C4—C5—C10 | −4.6 (13) | C35—C36—C37—C38 | 54.4 (9) |
C10—C5—C6—C7 | −48.0 (10) | C36—C37—C38—C39 | −54.9 (8) |
C5—C6—C7—C8 | 52.5 (9) | C37—C38—C39—C40 | 56.8 (8) |
C6—C7—C8—C9 | −56.8 (8) | C32—C31—C40—C50 | −75.4 (8) |
C7—C8—C9—C10 | 58.3 (7) | C32—C31—C40—C35 | 45.4 (8) |
C2—C1—C10—C5 | 45.3 (8) | C34—C35—C40—C31 | −15.8 (10) |
C2—C1—C10—C20 | −72.9 (8) | C36—C35—C40—C39 | 50.9 (8) |
C4—C5—C10—C1 | −17.5 (10) | C38—C39—C40—C35 | −52.0 (7) |
C6—C5—C10—C9 | 45.3 (8) | C41—C42—C43—C51 | −68.0 (8) |
C8—C9—C10—C5 | −50.8 (7) | C47—C43—C44—C45 | 38.1 (7) |
C11—C12—C13—C21 | −67.0 (8) | C43—C44—C45—C46 | −38.0 (8) |
C17—C13—C14—C15 | 40.0 (6) | C44—C45—C46—C47 | 22.2 (8) |
C13—C14—C15—C16 | −36.8 (7) | C45—C46—C47—C43 | 1.2 (8) |
C14—C15—C16—C17 | 19.7 (8) | C44—C43—C47—C46 | −23.5 (7) |
C15—C16—C17—C13 | 5.6 (8) | C46—C47—C48—C49 | −177.8 (7) |
C14—C13—C17—C16 | −27.8 (6) | H9—C9—C8—H8 | −178.0 |
C16—C17—C18—C19 | −174.5 (7) | H39—C39—C38—H38 | −179.1 |
C40—C31—C32—C33 | −54.8 (9) | C21—C13—C14—H14 | 176.0 |
C31—C32—C33—C34 | 33.3 (10) | C51—C43—C44—H44 | 176.1 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C21—H21C···O2i | 0.96 | 2.745 | 3.625 (10) | 153 |
C21—H21B···O31i | 0.96 | 2.813 | 3.723 (10) | 159 |
C32—H32B···O2ii | 0.97 | 2.453 | 3.237 (10) | 138 |
C45—H45A···O1iii | 0.97 | 2.425 | 3.274 (11) | 146 |
C50—H50B···O32iii | 0.96 | 2.759 | 3.641 (10) | 153 |
C51—H51B···O1iii | 0.96 | 2.725 | 3.678 (12) | 172 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) x−1, y, z; (iii) −x+1, y−1/2, −z+2. |
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.