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The title compound, C21H30O3 was synthetized by the epimerization of 17-oxoandrost-5-en-3β-yl acetate. There are four fused rings. The A/B and B/C ring fusions are trans, whereas the C/D ring fusion is cis. Rings A and C adopt chair conformations, ring B a distorted half-chair conformation and ring D a 14β-envelope conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680604222X/lh2163sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680604222X/lh2163Isup2.hkl
Contains datablock I

CCDC reference: 627969

Key indicators

  • Single-crystal X-ray study
  • T = 133 K
  • Mean [sigma](C-C) = 0.004 Å
  • Disorder in main residue
  • R factor = 0.039
  • wR factor = 0.101
  • Data-to-parameter ratio = 7.0

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............ 24.69 Deg.
Author Response: The value is only slightly under the requirements of Acta E. Whereas the resolution is 0.85 A, the data set is still very strong at this resolution, about 10 sigma.

Alert level B PLAT063_ALERT_3_B Crystal Probably too Large for Beam Size ....... 1.00 mm
Alert level C REFNR01_ALERT_3_C Ratio of reflections to parameters is < 8 for a non-centrosymmetric structure, where ZMAX < 18 sine(theta)/lambda 0.5877 Proportion of unique data used 1.0000 Ratio reflections to parameters 7.0130 THETM01_ALERT_3_C The value of sine(theta_max)/wavelength is less than 0.590 Calculated sin(theta_max)/wavelength = 0.5877 PLAT023_ALERT_3_C Resolution (too) Low [sin(th)/Lambda < 0.6]..... 24.69 Deg. PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.01 PLAT301_ALERT_3_C Main Residue Disorder ......................... 4.00 Perc.
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 24.69 From the CIF: _reflns_number_total 1613 Count of symmetry unique reflns 1668 Completeness (_total/calc) 96.70% 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 PLAT791_ALERT_1_G Confirm the Absolute Configuration of C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C8 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C9 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S
1 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 7 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 8 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

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXL97.

17-Oxo-13α-androst-5-en-3β-yl acetate top
Crystal data top
C21H30O3F(000) = 360
Mr = 330.45Dx = 1.190 Mg m3
Monoclinic, P21Melting point = 144–145 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71073 Å
a = 6.332 (2) ÅCell parameters from 2917 reflections
b = 10.729 (2) Åθ = 2.4–24.7°
c = 13.787 (2) ŵ = 0.08 mm1
β = 100.04 (3)°T = 133 K
V = 922.3 (4) Å3Prism, colourless
Z = 21.00 × 0.80 × 0.60 mm
Data collection top
Stoe IPDS-II
diffractometer
1613 independent reflections
Radiation source: fine-focus sealed tube1459 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.048
ω scansθmax = 24.7°, θmin = 2.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)
h = 77
Tmin = 0.927, Tmax = 0.955k = 1212
2917 measured reflectionsl = 016
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 0.91 w = 1/[σ2(Fo2) + (0.0867P)2]
where P = (Fo2 + 2Fc2)/3
1613 reflections(Δ/σ)max < 0.001
230 parametersΔρmax = 0.21 e Å3
41 restraintsΔρmin = 0.15 e Å3
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*/UeqOcc. (<1)
O30.6611 (3)0.5935 (2)0.94324 (16)0.0502 (6)
O10.2038 (3)0.10723 (17)0.63349 (13)0.0374 (4)
C140.1568 (4)0.5970 (2)0.78362 (17)0.0309 (5)
H140.00690.62910.77840.037*
C40.0539 (4)0.0996 (3)0.61213 (18)0.0342 (6)
H4A0.08210.05760.60560.041*
H4B0.13930.10990.54530.041*
C110.2532 (4)0.3733 (2)0.91051 (17)0.0331 (6)
H11A0.40340.36260.90070.040*
H11B0.22110.30650.95530.040*
C50.0052 (4)0.2261 (2)0.65826 (17)0.0307 (5)
C30.1779 (4)0.0184 (2)0.6736 (2)0.0351 (6)
H30.32250.05590.67370.042*
C90.1025 (4)0.3607 (2)0.81112 (17)0.0309 (5)
H90.04650.37550.82350.037*
C20.0595 (5)0.0086 (3)0.7783 (2)0.0387 (6)
H2A0.07930.03420.77900.046*
H2B0.14490.04160.81770.046*
C100.1059 (4)0.2275 (2)0.76606 (17)0.0301 (5)
C80.1504 (4)0.4630 (2)0.74016 (17)0.0307 (5)
H80.29420.44510.72270.037*
C130.2731 (4)0.6076 (2)0.89178 (18)0.0329 (6)
C60.0593 (4)0.3295 (3)0.60671 (18)0.0349 (6)
H60.13120.32050.54060.042*
C70.0150 (4)0.4590 (3)0.64524 (19)0.0378 (6)
H7A0.15060.49660.65770.045*
H7B0.03750.50980.59440.045*
C10.0196 (4)0.1382 (3)0.82403 (18)0.0349 (6)
H1A0.06140.12900.89190.042*
H1B0.15960.17660.82870.042*
C200.3633 (5)0.1257 (3)0.5573 (2)0.0461 (7)
C120.2294 (4)0.5001 (3)0.95796 (19)0.0358 (6)
H12A0.08200.50810.97220.043*
H12B0.33050.50521.02130.043*
C180.2177 (4)0.7328 (3)0.9372 (2)0.0378 (6)
H18A0.26670.80200.90040.057*
H18B0.28910.73701.00610.057*
H18C0.06210.73870.93380.057*
C150.2856 (4)0.6854 (3)0.7273 (2)0.0399 (6)
H15A0.26780.66200.65690.048*
H15B0.23910.77290.73230.048*
C170.5082 (4)0.6188 (3)0.88010 (19)0.0374 (6)
C210.3705 (4)0.2573 (3)0.5211 (2)0.0405 (6)
H21A0.45020.30880.56110.061*
H21B0.22410.28940.52650.061*
H21C0.44200.26000.45220.061*
O20.517 (5)0.056 (5)0.554 (7)0.073 (12)0.25 (9)
O2A0.472 (4)0.0427 (6)0.514 (2)0.074 (5)0.75 (9)
C190.3378 (4)0.1793 (3)0.77203 (19)0.0364 (6)
H19A0.40080.16320.84100.055*
H19B0.42340.24220.74480.055*
H19C0.33610.10200.73410.055*
C160.5196 (4)0.6679 (3)0.7788 (2)0.0465 (7)
H16A0.59440.60790.74210.056*
H16B0.59740.74830.78330.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O30.0304 (9)0.0583 (13)0.0576 (12)0.0013 (9)0.0042 (9)0.0067 (10)
O10.0368 (9)0.0335 (9)0.0403 (10)0.0014 (8)0.0024 (8)0.0032 (8)
C140.0246 (10)0.0370 (13)0.0306 (12)0.0026 (10)0.0036 (9)0.0018 (10)
C40.0326 (12)0.0396 (13)0.0295 (12)0.0021 (11)0.0025 (10)0.0025 (11)
C110.0340 (12)0.0348 (13)0.0291 (12)0.0011 (10)0.0017 (10)0.0035 (10)
C50.0246 (10)0.0387 (13)0.0293 (11)0.0021 (10)0.0056 (9)0.0003 (10)
C30.0328 (13)0.0327 (13)0.0400 (14)0.0017 (10)0.0070 (11)0.0017 (11)
C90.0254 (10)0.0375 (13)0.0299 (12)0.0024 (10)0.0051 (10)0.0019 (10)
C20.0449 (15)0.0349 (13)0.0364 (13)0.0030 (11)0.0078 (12)0.0005 (11)
C100.0247 (11)0.0355 (13)0.0294 (11)0.0026 (10)0.0028 (9)0.0003 (10)
C80.0277 (11)0.0338 (13)0.0300 (12)0.0008 (10)0.0038 (10)0.0004 (11)
C130.0264 (11)0.0363 (13)0.0351 (13)0.0003 (10)0.0026 (10)0.0028 (11)
C60.0332 (12)0.0432 (14)0.0272 (11)0.0003 (11)0.0022 (10)0.0001 (11)
C70.0412 (14)0.0390 (14)0.0310 (12)0.0042 (11)0.0005 (11)0.0018 (11)
C10.0357 (12)0.0381 (14)0.0313 (12)0.0003 (11)0.0064 (10)0.0012 (11)
C200.0403 (14)0.0354 (15)0.0580 (17)0.0019 (12)0.0044 (13)0.0025 (13)
C120.0333 (13)0.0432 (14)0.0295 (12)0.0020 (11)0.0016 (11)0.0013 (11)
C180.0383 (13)0.0370 (14)0.0373 (13)0.0011 (11)0.0049 (11)0.0033 (11)
C150.0399 (14)0.0377 (14)0.0418 (14)0.0033 (11)0.0058 (12)0.0003 (11)
C170.0301 (12)0.0356 (14)0.0447 (14)0.0008 (10)0.0015 (11)0.0085 (11)
C210.0377 (13)0.0386 (14)0.0450 (14)0.0055 (11)0.0066 (12)0.0021 (12)
O20.048 (8)0.054 (10)0.10 (3)0.014 (7)0.021 (11)0.027 (14)
O2A0.070 (5)0.0367 (19)0.095 (8)0.003 (2)0.042 (5)0.007 (3)
C190.0282 (12)0.0406 (14)0.0386 (13)0.0060 (10)0.0011 (10)0.0022 (11)
C160.0340 (13)0.0521 (17)0.0550 (17)0.0101 (12)0.0125 (13)0.0027 (14)
Geometric parameters (Å, º) top
O3—C171.214 (3)C13—C121.526 (4)
O1—C201.339 (3)C13—C171.530 (3)
O1—C31.456 (3)C13—C181.548 (4)
C14—C151.545 (4)C6—C71.496 (4)
C14—C131.548 (3)C6—H60.9500
C14—C81.556 (4)C7—H7A0.9900
C14—H141.0000C7—H7B0.9900
C4—C51.508 (4)C1—H1A0.9900
C4—C31.525 (4)C1—H1B0.9900
C4—H4A0.9900C20—O21.225 (14)
C4—H4B0.9900C20—O2A1.218 (6)
C11—C91.533 (3)C20—C211.496 (4)
C11—C121.529 (4)C12—H12A0.9900
C11—H11A0.9900C12—H12B0.9900
C11—H11B0.9900C18—H18A0.9800
C5—C61.329 (4)C18—H18B0.9800
C5—C101.529 (3)C18—H18C0.9800
C3—C21.509 (4)C15—C161.539 (4)
C3—H31.0000C15—H15A0.9900
C9—C81.535 (3)C15—H15B0.9900
C9—C101.560 (3)C17—C161.506 (4)
C9—H91.0000C21—H21A0.9800
C2—C11.530 (4)C21—H21B0.9800
C2—H2A0.9900C21—H21C0.9800
C2—H2B0.9900C19—H19A0.9800
C10—C191.545 (3)C19—H19B0.9800
C10—C11.553 (3)C19—H19C0.9800
C8—C71.528 (3)C16—H16A0.9900
C8—H81.0000C16—H16B0.9900
C20—O1—C3117.06 (19)C5—C6—H6117.6
C15—C14—C13103.60 (19)C7—C6—H6117.6
C15—C14—C8110.7 (2)C6—C7—C8112.9 (2)
C13—C14—C8114.5 (2)C6—C7—H7A109.0
C15—C14—H14109.3C8—C7—H7A109.0
C13—C14—H14109.3C6—C7—H7B109.0
C8—C14—H14109.3C8—C7—H7B109.0
C5—C4—C3111.5 (2)H7A—C7—H7B107.8
C5—C4—H4A109.3C2—C1—C10114.3 (2)
C3—C4—H4A109.3C2—C1—H1A108.7
C5—C4—H4B109.3C10—C1—H1A108.7
C3—C4—H4B109.3C2—C1—H1B108.7
H4A—C4—H4B108.0C10—C1—H1B108.7
C9—C11—C12111.6 (2)H1A—C1—H1B107.6
C9—C11—H11A109.3O2—C20—O1115 (2)
C12—C11—H11A109.3O2A—C20—O1124.3 (5)
C9—C11—H11B109.3O2—C20—C21126.2 (14)
C12—C11—H11B109.3O2A—C20—C21122.9 (7)
H11A—C11—H11B108.0O1—C20—C21112.1 (2)
C6—C5—C4120.7 (2)C13—C12—C11112.1 (2)
C6—C5—C10122.9 (2)C13—C12—H12A109.2
C4—C5—C10116.4 (2)C11—C12—H12A109.2
O1—C3—C2107.6 (2)C13—C12—H12B109.2
O1—C3—C4110.6 (2)C11—C12—H12B109.2
C2—C3—C4110.7 (2)H12A—C12—H12B107.9
O1—C3—H3109.3C13—C18—H18A109.5
C2—C3—H3109.3C13—C18—H18B109.5
C4—C3—H3109.3H18A—C18—H18B109.5
C11—C9—C8110.22 (19)C13—C18—H18C109.5
C11—C9—C10112.74 (19)H18A—C18—H18C109.5
C8—C9—C10112.51 (19)H18B—C18—H18C109.5
C11—C9—H9107.0C16—C15—C14104.1 (2)
C8—C9—H9107.0C16—C15—H15A110.9
C10—C9—H9107.0C14—C15—H15A110.9
C3—C2—C1110.4 (2)C16—C15—H15B110.9
C3—C2—H2A109.6C14—C15—H15B110.9
C1—C2—H2A109.6H15A—C15—H15B109.0
C3—C2—H2B109.6O3—C17—C16125.6 (2)
C1—C2—H2B109.6O3—C17—C13125.2 (3)
H2A—C2—H2B108.1C16—C17—C13109.2 (2)
C5—C10—C19108.66 (19)C20—C21—H21A109.5
C5—C10—C1107.72 (19)C20—C21—H21B109.5
C19—C10—C1109.4 (2)H21A—C21—H21B109.5
C5—C10—C9111.10 (19)C20—C21—H21C109.5
C19—C10—C9111.4 (2)H21A—C21—H21C109.5
C1—C10—C9108.5 (2)H21B—C21—H21C109.5
C7—C8—C9110.1 (2)C10—C19—H19A109.5
C7—C8—C14108.89 (19)C10—C19—H19B109.5
C9—C8—C14114.2 (2)H19A—C19—H19B109.5
C7—C8—H8107.8C10—C19—H19C109.5
C9—C8—H8107.8H19A—C19—H19C109.5
C14—C8—H8107.8H19B—C19—H19C109.5
C12—C13—C17113.8 (2)C17—C16—C15105.9 (2)
C12—C13—C18109.7 (2)C17—C16—H16A110.6
C17—C13—C18105.5 (2)C15—C16—H16A110.6
C12—C13—C14114.5 (2)C17—C16—H16B110.6
C17—C13—C14102.27 (19)C15—C16—H16B110.6
C18—C13—C14110.5 (2)H16A—C16—H16B108.7
C5—C6—C7124.7 (2)
C3—C4—C5—C6126.6 (3)C15—C14—C13—C1736.9 (2)
C3—C4—C5—C1052.8 (3)C8—C14—C13—C1783.8 (2)
C20—O1—C3—C2157.3 (2)C15—C14—C13—C1875.1 (2)
C20—O1—C3—C481.6 (3)C8—C14—C13—C18164.2 (2)
C5—C4—C3—O1174.08 (18)C4—C5—C6—C7179.0 (3)
C5—C4—C3—C254.9 (3)C10—C5—C6—C71.6 (4)
C12—C11—C9—C859.3 (3)C5—C6—C7—C815.4 (4)
C12—C11—C9—C10174.0 (2)C9—C8—C7—C644.6 (3)
O1—C3—C2—C1178.0 (2)C14—C8—C7—C6170.5 (2)
C4—C3—C2—C157.0 (3)C3—C2—C1—C1057.0 (3)
C6—C5—C10—C19111.2 (3)C5—C10—C1—C250.7 (3)
C4—C5—C10—C1969.4 (3)C19—C10—C1—C267.3 (3)
C6—C5—C10—C1130.3 (3)C9—C10—C1—C2171.06 (19)
C4—C5—C10—C149.0 (3)C3—O1—C20—O228 (6)
C6—C5—C10—C911.7 (3)C3—O1—C20—O2A8 (2)
C4—C5—C10—C9167.7 (2)C3—O1—C20—C21178.7 (2)
C11—C9—C10—C5167.26 (19)C17—C13—C12—C1169.5 (3)
C8—C9—C10—C541.9 (3)C18—C13—C12—C11172.6 (2)
C11—C9—C10—C1946.0 (3)C14—C13—C12—C1147.7 (3)
C8—C9—C10—C1979.4 (2)C9—C11—C12—C1358.0 (3)
C11—C9—C10—C174.5 (2)C13—C14—C15—C1637.2 (3)
C8—C9—C10—C1160.09 (18)C8—C14—C15—C1686.0 (2)
C11—C9—C8—C7174.0 (2)C12—C13—C17—O333.4 (4)
C10—C9—C8—C759.2 (3)C18—C13—C17—O386.9 (3)
C11—C9—C8—C1451.1 (3)C14—C13—C17—O3157.5 (3)
C10—C9—C8—C14177.89 (18)C12—C13—C17—C16147.6 (2)
C15—C14—C8—C777.9 (2)C18—C13—C17—C1692.1 (2)
C13—C14—C8—C7165.4 (2)C14—C13—C17—C1623.5 (3)
C15—C14—C8—C9158.56 (19)O3—C17—C16—C15179.8 (3)
C13—C14—C8—C941.9 (3)C13—C17—C16—C150.7 (3)
C15—C14—C13—C12160.5 (2)C14—C15—C16—C1722.5 (3)
C8—C14—C13—C1239.8 (3)
 

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