Download citation
Download citation
link to html
The synthetic steroid 21-acet­oxy-17α-4-pregnene-3,20-dione, C23H32O4, crystallizes with a single mol­ecule in the asymmetric unit. The mol­ecule contains four fused rings, typical of steroids. The cyclo­hexene ring A has nearly the conformation of a boat. One saturated six-membered ring, B, is inter­mediate between chair and half-chair conformations, while the other six-membered ring, C, is essentially a chair. The five-membered ring D tends towards a twist conformation. The ring junction A/B is quasi-trans, whereas the ring junctions B/C and C/D are both trans. The mol­ecule is slightly convex towards the β side.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007415/cf6413sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007415/cf6413Isup2.hkl
Contains datablock I

CCDC reference: 219638

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.054
  • wR factor = 0.155
  • Data-to-parameter ratio = 7.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low .... 0.83
Author Response: The data was collected more than 15 years before and we don't have either any crystal or the material to re-crystallize.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.86
Author Response: The data was collected more than 15 years before and we don't have either any crystal or the material to re-crystallize.

Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.63 PLAT199_ALERT_1_C Check the Reported cell_measurement_temperature 293 PLAT200_ALERT_1_C Check the Reported cell_ambient_temperature .... 293 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C6 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C11 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C15 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C10 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C13 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C22 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 71.04 From the CIF: _reflns_number_total 1885 Count of symmetry unique reflns 2272 Completeness (_total/calc) 82.97% 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
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: XDS (Kabsch, 1988); cell refinement: XDS; data reduction: XDS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2004); software used to prepare material for publication: SHELXL97.

21-Acetoxy-17α-4-pregnene-3,20-dione top
Crystal data top
C23H32O4F(000) = 808
Mr = 372.49Dx = 1.212 Mg m3
Dm = 1.23 Mg m3
Dm measured by flotation in benzene/bromoform
Orthorhombic, P212121Cu Kα radiation, λ = 1.54180 Å
Hall symbol: P 2ac 2abCell parameters from 50 reflections
a = 7.590 (2) Åθ = 4.0–71.0°
b = 12.098 (3) ŵ = 0.65 mm1
c = 22.228 (4) ÅT = 293 K
V = 2041.1 (8) Å3Parallelepiped, colorless
Z = 40.42 × 0.35 × 0.30 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.000
Radiation source: fine-focus sealed tubeθmax = 71.0°, θmin = 4.0°
Graphite monochromatorh = 09
ω–2θ scansk = 014
1885 measured reflectionsl = 027
1885 independent reflections3 standard reflections every 150 reflections
1882 reflections with I > 2σ(I) intensity decay: none
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0939P)2 + 0.6818P]
where P = (Fo2 + 2Fc2)/3
1885 reflections(Δ/σ)max < 0.001
247 parametersΔρmax = 0.20 e Å3
0 restraintsΔρmin = 0.18 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*/Ueq
C10.1389 (6)0.0308 (3)0.5545 (2)0.0800 (12)
H1A0.11580.05850.51430.096*
H1B0.25540.05580.56620.096*
C20.1374 (6)0.0947 (3)0.5531 (2)0.0849 (13)
H2A0.22150.12050.52340.102*
H2B0.17350.12290.59200.102*
C30.0391 (6)0.1380 (3)0.53824 (17)0.0743 (10)
O30.0592 (5)0.2283 (3)0.51497 (16)0.1028 (11)
C40.1875 (6)0.0700 (3)0.5555 (2)0.0793 (11)
H40.29970.09570.54610.095*
C50.1749 (5)0.0280 (3)0.58421 (18)0.0683 (9)
C60.3323 (7)0.0856 (4)0.6090 (3)0.1043 (17)
H6A0.33550.07530.65220.125*
H6B0.43780.05240.59220.125*
C70.3324 (5)0.2103 (4)0.5949 (3)0.0964 (16)
H7A0.34160.22150.55180.116*
H7B0.43320.24510.61390.116*
C80.1629 (5)0.2629 (3)0.61813 (18)0.0644 (9)
H80.15480.25110.66170.077*
C90.0063 (4)0.2071 (3)0.58758 (15)0.0555 (8)
H90.02440.21730.54430.067*
C100.0037 (5)0.0798 (3)0.59761 (15)0.0596 (8)
C110.1688 (5)0.2646 (3)0.6022 (2)0.0810 (12)
H11A0.20020.24840.64350.097*
H11B0.26010.23400.57660.097*
C120.1649 (5)0.3896 (3)0.5938 (2)0.0758 (11)
H12A0.15290.40660.55140.091*
H12B0.27530.42080.60780.091*
C130.0132 (4)0.4417 (3)0.62837 (15)0.0571 (8)
C140.1553 (5)0.3866 (3)0.60524 (18)0.0637 (9)
H140.15290.39410.56140.076*
C150.3033 (6)0.4615 (4)0.6272 (3)0.0994 (16)
H15A0.33920.44130.66770.119*
H15B0.40470.45660.60080.119*
C160.2251 (5)0.5780 (4)0.6262 (3)0.0921 (14)
H16A0.24210.61390.66480.111*
H16B0.28150.62230.59530.111*
C170.0263 (5)0.5651 (3)0.61260 (18)0.0660 (9)
H170.00970.57440.56920.079*
C180.0374 (8)0.4307 (4)0.69605 (17)0.0895 (14)
H18A0.04360.35390.70670.134*
H18B0.06050.46440.71630.134*
H18C0.14450.46700.70790.134*
C190.0495 (9)0.0513 (4)0.66325 (19)0.1026 (18)
H19A0.03570.08440.68960.154*
H19B0.16470.07920.67270.154*
H19C0.04800.02750.66840.154*
C200.0852 (6)0.6496 (3)0.64385 (19)0.0695 (10)
O200.0333 (5)0.7118 (3)0.68249 (16)0.0976 (11)
C210.2763 (5)0.6557 (3)0.6228 (2)0.0751 (11)
H21A0.33370.58590.63150.090*
H21B0.27820.66620.57960.090*
O210.3734 (4)0.7424 (2)0.65043 (13)0.0786 (8)
C220.4392 (7)0.7221 (5)0.7056 (2)0.0902 (13)
O220.4175 (6)0.6354 (4)0.73041 (18)0.1218 (13)
C230.5438 (10)0.8178 (6)0.7272 (3)0.133 (2)
H23A0.55860.81270.77000.200*
H23B0.48320.88520.71750.200*
H23C0.65720.81760.70810.200*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.063 (2)0.063 (2)0.114 (3)0.0026 (19)0.004 (2)0.013 (2)
C20.079 (3)0.065 (2)0.111 (3)0.002 (2)0.008 (3)0.017 (2)
C30.094 (3)0.0577 (19)0.071 (2)0.005 (2)0.011 (2)0.0003 (17)
O30.121 (3)0.0721 (19)0.116 (2)0.007 (2)0.025 (2)0.0190 (17)
C40.072 (2)0.070 (2)0.096 (3)0.010 (2)0.008 (2)0.004 (2)
C50.061 (2)0.066 (2)0.078 (2)0.0097 (18)0.0030 (19)0.0033 (18)
C60.071 (3)0.082 (3)0.160 (5)0.019 (2)0.028 (3)0.016 (3)
C70.048 (2)0.082 (3)0.159 (5)0.005 (2)0.007 (3)0.021 (3)
C80.0524 (18)0.068 (2)0.073 (2)0.0011 (17)0.0076 (18)0.0027 (17)
C90.0464 (17)0.0599 (17)0.0602 (17)0.0023 (15)0.0011 (16)0.0021 (15)
C100.061 (2)0.0593 (17)0.0587 (17)0.0002 (16)0.0076 (17)0.0003 (15)
C110.0493 (19)0.064 (2)0.130 (4)0.0031 (17)0.006 (2)0.025 (2)
C120.0502 (19)0.064 (2)0.113 (3)0.0029 (17)0.010 (2)0.020 (2)
C130.0511 (17)0.0581 (18)0.0620 (17)0.0039 (16)0.0035 (16)0.0046 (14)
C140.0472 (17)0.066 (2)0.078 (2)0.0070 (16)0.0016 (17)0.0035 (17)
C150.055 (2)0.084 (3)0.159 (5)0.010 (2)0.015 (3)0.021 (3)
C160.056 (2)0.076 (2)0.145 (4)0.018 (2)0.006 (3)0.008 (3)
C170.0578 (19)0.064 (2)0.076 (2)0.0095 (17)0.0016 (18)0.0021 (17)
C180.124 (4)0.076 (2)0.068 (2)0.005 (3)0.016 (3)0.0002 (19)
C190.156 (5)0.075 (3)0.077 (3)0.007 (3)0.042 (3)0.011 (2)
C200.072 (2)0.0567 (19)0.080 (2)0.0077 (18)0.007 (2)0.0041 (18)
O200.092 (2)0.086 (2)0.114 (2)0.0083 (18)0.0190 (19)0.0350 (18)
C210.070 (2)0.064 (2)0.092 (3)0.0043 (19)0.009 (2)0.016 (2)
O210.0780 (18)0.0650 (15)0.0928 (19)0.0075 (14)0.0012 (15)0.0088 (13)
C220.083 (3)0.102 (3)0.086 (3)0.006 (3)0.002 (3)0.008 (3)
O220.121 (3)0.131 (3)0.114 (3)0.000 (3)0.007 (2)0.028 (2)
C230.123 (5)0.149 (5)0.128 (5)0.023 (4)0.020 (4)0.048 (4)
Geometric parameters (Å, º) top
C1—C21.519 (5)C12—H12B0.970
C1—C101.524 (6)C13—C181.521 (5)
C1—H1A0.970C13—C141.531 (5)
C1—H1B0.970C13—C171.563 (5)
C2—C31.476 (6)C14—C151.524 (5)
C2—H2A0.970C14—H140.980
C2—H2B0.970C15—C161.530 (7)
C3—O31.218 (4)C15—H15A0.970
C3—C41.446 (6)C15—H15B0.970
C4—C51.351 (6)C16—C171.547 (5)
C4—H40.930C16—H16A0.970
C5—C61.488 (7)C16—H16B0.970
C5—C101.522 (5)C17—C201.497 (6)
C6—C71.541 (7)C17—H170.980
C6—H6A0.970C18—H18A0.960
C6—H6B0.970C18—H18B0.960
C7—C81.525 (6)C18—H18C0.960
C7—H7A0.970C19—H19A0.960
C7—H7B0.970C19—H19B0.960
C8—C141.525 (5)C19—H19C0.960
C8—C91.526 (5)C20—O201.208 (5)
C8—H80.980C20—C211.526 (6)
C9—C111.535 (5)C21—O211.422 (5)
C9—C101.558 (5)C21—H21A0.970
C9—H90.980C21—H21B0.970
C10—C191.539 (5)O21—C221.346 (6)
C11—C121.523 (5)C22—O221.197 (6)
C11—H11A0.970C22—C231.484 (8)
C11—H11B0.970C23—H23A0.960
C12—C131.521 (5)C23—H23B0.960
C12—H12A0.970C23—H23C0.960
C2—C1—C10113.3 (4)H12A—C12—H12B108.0
C2—C1—H1A108.9C18—C13—C12111.8 (4)
C10—C1—H1A108.9C18—C13—C14113.3 (3)
C2—C1—H1B108.9C12—C13—C14106.4 (3)
C10—C1—H1B108.9C18—C13—C17109.2 (3)
H1A—C1—H1B107.7C12—C13—C17115.3 (3)
C3—C2—C1111.5 (4)C14—C13—C17100.4 (3)
C3—C2—H2A109.3C15—C14—C8119.7 (4)
C1—C2—H2A109.3C15—C14—C13104.4 (3)
C3—C2—H2B109.3C8—C14—C13113.3 (3)
C1—C2—H2B109.3C15—C14—H14106.2
H2A—C2—H2B108.0C8—C14—H14106.2
O3—C3—C4121.7 (4)C13—C14—H14106.2
O3—C3—C2121.8 (4)C14—C15—C16104.9 (3)
C4—C3—C2116.5 (3)C14—C15—H15A110.8
C5—C4—C3124.7 (4)C16—C15—H15A110.8
C5—C4—H4117.6C14—C15—H15B110.8
C3—C4—H4117.6C16—C15—H15B110.8
C4—C5—C6121.9 (4)H15A—C15—H15B108.8
C4—C5—C10121.1 (4)C15—C16—C17106.8 (3)
C6—C5—C10116.7 (3)C15—C16—H16A110.4
C5—C6—C7112.6 (4)C17—C16—H16A110.4
C5—C6—H6A109.1C15—C16—H16B110.4
C7—C6—H6A109.1C17—C16—H16B110.4
C5—C6—H6B109.1H16A—C16—H16B108.6
C7—C6—H6B109.1C20—C17—C16113.0 (4)
H6A—C6—H6B107.8C20—C17—C13116.1 (3)
C8—C7—C6109.8 (4)C16—C17—C13103.8 (3)
C8—C7—H7A109.7C20—C17—H17107.8
C6—C7—H7A109.7C16—C17—H17107.8
C8—C7—H7B109.7C13—C17—H17107.8
C6—C7—H7B109.7C13—C18—H18A109.5
H7A—C7—H7B108.2C13—C18—H18B109.5
C14—C8—C9108.7 (3)H18A—C18—H18B109.5
C14—C8—C7112.2 (3)C13—C18—H18C109.5
C9—C8—C7108.8 (3)H18A—C18—H18C109.5
C14—C8—H8109.0H18B—C18—H18C109.5
C9—C8—H8109.0C10—C19—H19A109.5
C7—C8—H8109.0C10—C19—H19B109.5
C8—C9—C11112.3 (3)H19A—C19—H19B109.5
C8—C9—C10114.3 (3)C10—C19—H19C109.5
C11—C9—C10112.1 (3)H19A—C19—H19C109.5
C8—C9—H9105.8H19B—C19—H19C109.5
C11—C9—H9105.8O20—C20—C17124.8 (4)
C10—C9—H9105.8O20—C20—C21119.9 (4)
C5—C10—C1108.5 (3)C17—C20—C21115.3 (3)
C5—C10—C19107.1 (4)O21—C21—C20113.4 (3)
C1—C10—C19111.0 (4)O21—C21—H21A108.9
C5—C10—C9109.6 (3)C20—C21—H21A108.9
C1—C10—C9109.1 (3)O21—C21—H21B108.9
C19—C10—C9111.6 (3)C20—C21—H21B108.9
C12—C11—C9114.1 (3)H21A—C21—H21B107.7
C12—C11—H11A108.7C22—O21—C21116.8 (4)
C9—C11—H11A108.7O22—C22—O21122.0 (5)
C12—C11—H11B108.7O22—C22—C23127.4 (5)
C9—C11—H11B108.7O21—C22—C23110.6 (5)
H11A—C11—H11B107.6C22—C23—H23A109.5
C11—C12—C13111.4 (4)C22—C23—H23B109.5
C11—C12—H12A109.3H23A—C23—H23B109.5
C13—C12—H12A109.3C22—C23—H23C109.5
C11—C12—H12B109.3H23A—C23—H23C109.5
C13—C12—H12B109.3H23B—C23—H23C109.5
C10—C1—C2—C356.0 (6)C11—C12—C13—C1866.5 (5)
C1—C2—C3—O3154.4 (4)C11—C12—C13—C1457.6 (4)
C1—C2—C3—C428.5 (6)C11—C12—C13—C17168.0 (4)
O3—C3—C4—C5176.4 (4)C9—C8—C14—C15176.1 (4)
C2—C3—C4—C50.7 (6)C7—C8—C14—C1555.8 (6)
C3—C4—C5—C6170.4 (5)C9—C8—C14—C1360.0 (4)
C3—C4—C5—C104.1 (6)C7—C8—C14—C13179.7 (3)
C4—C5—C6—C7135.7 (5)C18—C13—C14—C1572.0 (4)
C10—C5—C6—C749.5 (7)C12—C13—C14—C15164.8 (4)
C5—C6—C7—C855.9 (7)C17—C13—C14—C1544.2 (4)
C6—C7—C8—C14179.8 (4)C18—C13—C14—C859.9 (4)
C6—C7—C8—C959.5 (5)C12—C13—C14—C863.3 (4)
C14—C8—C9—C1150.3 (4)C17—C13—C14—C8176.2 (3)
C7—C8—C9—C11172.7 (4)C8—C14—C15—C16161.2 (4)
C14—C8—C9—C10179.4 (3)C13—C14—C15—C1633.1 (5)
C7—C8—C9—C1058.2 (4)C14—C15—C16—C178.1 (6)
C4—C5—C10—C121.7 (5)C15—C16—C17—C20145.7 (4)
C6—C5—C10—C1163.5 (4)C15—C16—C17—C1319.1 (6)
C4—C5—C10—C1998.2 (4)C18—C13—C17—C2043.8 (5)
C6—C5—C10—C1976.7 (5)C12—C13—C17—C2083.0 (4)
C4—C5—C10—C9140.6 (4)C14—C13—C17—C20163.1 (3)
C6—C5—C10—C944.6 (5)C18—C13—C17—C1680.9 (4)
C2—C1—C10—C551.1 (5)C12—C13—C17—C16152.3 (4)
C2—C1—C10—C1966.4 (5)C14—C13—C17—C1638.4 (4)
C2—C1—C10—C9170.4 (4)C16—C17—C20—O2010.3 (6)
C8—C9—C10—C549.1 (4)C13—C17—C20—O20109.6 (5)
C11—C9—C10—C5178.3 (3)C16—C17—C20—C21168.5 (4)
C8—C9—C10—C1167.7 (3)C13—C17—C20—C2171.7 (5)
C11—C9—C10—C163.1 (4)O20—C20—C21—O213.3 (6)
C8—C9—C10—C1969.4 (4)C17—C20—C21—O21175.5 (3)
C11—C9—C10—C1959.9 (5)C20—C21—O21—C2282.1 (5)
C8—C9—C11—C1249.0 (5)C21—O21—C22—O220.0 (7)
C10—C9—C11—C12179.2 (4)C21—O21—C22—C23177.4 (4)
C9—C11—C12—C1353.2 (5)
Endocyclic torsion angles (°) about the ring junctions top
JunctionAtomsTorsion angleCharacteristics
A/BC4—C5—C10—C121.7 (5)°Quasi-trans
C6—C5—C10—C9-44.6 (5)°
B/CC7—C8—C9—C10-58.2 (4)°Trans
C14—C8—C9—C1150.3 (4)°
C/DC12—C13—C14—C863.4 (4)°Trans
C17—C13—C14—C15-44.2 (4)°
Functional groups with their orientations, deviations from the C5–C17 mean plane (Å) and angles subtended to the C5–C17 mean plane (°) top
Functional groupOrientationDeviationAngle
C18β-axial1.894 (4)87.6 (2)
C19β-axial1.678 (4)79.3 (2)
O3α-axial-1.290 (4)19.5 (2)
O20β-axial1.223 (4)37.5 (3)
C22β-axial1.980 (4)72.4 (2)
 

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds