Download citation
Download citation
link to html
The title compound, C24H32O5, has rings A and C in regular chair, ring B in a distorted half-chair and ring D in an envelope conformation. The dioxolane ring adopts a twist conformation.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806033745/bt2164sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806033745/bt2164Isup2.hkl
Contains datablock I

CCDC reference: 620693

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.007 Å
  • R factor = 0.052
  • wR factor = 0.154
  • Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 3.00 Sigma PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.62 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C23 - C24 .. 5.16 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C22 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C24 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C20 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7 PLAT412_ALERT_2_C Short Intra XH3 .. XHn H18B .. H22A .. 1.89 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 25.16 From the CIF: _reflns_number_total 2190 Count of symmetry unique reflns 2189 Completeness (_total/calc) 100.05% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 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 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 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C15 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C16 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 8 ALERT level C = Check and explain 11 ALERT level G = General alerts; check 10 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 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, (1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Version 1.05; Farrugia, 1997); software used to prepare material for publication: SHELXL97.

Methyl 17,17-ethylenedioxy-7-oxo-15β,16β-methylene-5-androstene-3β-carboxylate top
Crystal data top
C24H32O5F(000) = 864
Mr = 400.50Dx = 1.270 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 6.1020 (17) Åθ = 12.0–13.9°
b = 14.450 (3) ŵ = 0.09 mm1
c = 23.763 (8) ÅT = 293 K
V = 2095.3 (10) Å3Plate, colourless
Z = 40.50 × 0.40 × 0.20 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
Rint = 0.023
Radiation source: fine-focus sealed tubeθmax = 25.2°, θmin = 1.7°
Graphite monochromatorh = 07
ω/2θ scansk = 017
2301 measured reflectionsl = 128
2190 independent reflections3 standard reflections every 60 min
1285 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)] = 0.052H-atom parameters constrained
wR(F2) = 0.154 w = 1/[σ2(Fo2) + (0.0728P)2 + 0.3809P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.001
2190 reflectionsΔρmax = 0.20 e Å3
266 parametersΔρmin = 0.18 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.006 (2)
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
O10.5168 (6)0.2816 (3)1.10540 (17)0.0831 (12)
O20.2056 (10)0.3168 (4)1.1458 (3)0.144 (2)
O30.3455 (8)0.4825 (3)0.84376 (17)0.1056 (16)
O40.8664 (7)0.8599 (2)0.81102 (15)0.0706 (10)
O50.5117 (7)0.8473 (3)0.83701 (17)0.0849 (13)
C10.6343 (10)0.5226 (3)1.0530 (2)0.0668 (15)
H1A0.73010.57041.06770.080*
H1B0.48640.54731.05280.080*
C20.6412 (11)0.4405 (4)1.0928 (2)0.0740 (16)
H2A0.79130.41951.09710.089*
H2B0.58750.45911.12950.089*
C30.5019 (10)0.3627 (4)1.0701 (2)0.0693 (15)
H30.34880.38291.06770.083*
C40.5813 (10)0.3357 (3)1.0133 (2)0.0708 (15)
H4A0.48830.28680.99860.085*
H4B0.72880.31121.01650.085*
C50.5819 (8)0.4154 (3)0.9725 (2)0.0517 (12)
C60.4797 (9)0.4095 (3)0.9237 (2)0.0641 (14)
H60.40590.35500.91520.077*
C70.4763 (9)0.4837 (3)0.8826 (2)0.0607 (13)
C80.6412 (7)0.5600 (3)0.89026 (17)0.0457 (11)
H80.78700.53600.88100.055*
C90.6355 (7)0.5850 (3)0.95359 (19)0.0448 (11)
H90.48080.59650.96210.054*
C100.7020 (7)0.5020 (3)0.99161 (19)0.0476 (12)
C110.7546 (9)0.6755 (3)0.96848 (18)0.0581 (13)
H11A0.71050.69441.00600.070*
H11B0.91110.66360.96940.070*
C120.7108 (9)0.7551 (3)0.92776 (18)0.0569 (13)
H12A0.55890.77430.93090.068*
H12B0.80270.80740.93750.068*
C130.7584 (8)0.7251 (3)0.86762 (19)0.0465 (11)
C140.5982 (8)0.6448 (3)0.85509 (18)0.0468 (11)
H140.45680.66750.86890.056*
C150.5694 (10)0.6420 (4)0.7919 (2)0.0673 (15)
H150.43590.61390.77660.081*
C160.6382 (11)0.7369 (3)0.7703 (2)0.0705 (15)
H160.54630.76620.74160.085*
C170.7000 (8)0.7936 (3)0.8209 (2)0.0544 (12)
C181.0075 (7)0.7022 (4)0.8635 (2)0.0629 (14)
H18A1.08750.74060.88930.094*
H18B1.05780.71360.82590.094*
H18C1.03070.63830.87290.094*
C190.9499 (8)0.4831 (4)0.9884 (3)0.0756 (17)
H19A0.99340.47770.94980.113*
H19B0.98290.42661.00790.113*
H19C1.02800.53341.00570.113*
C200.3572 (12)0.2668 (4)1.1420 (3)0.0774 (16)
C210.3952 (12)0.1824 (4)1.1769 (2)0.0819 (17)
H21A0.25860.15091.18280.123*
H21B0.45610.20011.21260.123*
H21C0.49540.14201.15780.123*
C220.7629 (13)0.6525 (4)0.7541 (2)0.087 (2)
H22A0.90710.64400.77050.104*
H22B0.74870.63070.71570.104*
C230.7601 (13)0.9413 (4)0.7916 (3)0.095 (2)
H23A0.75380.94240.75080.114*
H23B0.83560.99630.80460.114*
C240.5364 (15)0.9353 (5)0.8162 (3)0.117 (3)
H24A0.51950.98050.84610.141*
H24B0.42680.94760.78760.141*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.058 (2)0.083 (3)0.109 (3)0.008 (2)0.007 (3)0.044 (2)
O20.120 (5)0.118 (4)0.195 (6)0.048 (4)0.074 (4)0.072 (4)
O30.123 (4)0.105 (3)0.089 (3)0.057 (3)0.039 (3)0.011 (3)
O40.070 (2)0.0561 (19)0.086 (2)0.009 (2)0.001 (2)0.0171 (19)
O50.075 (3)0.076 (3)0.104 (3)0.035 (2)0.012 (3)0.027 (2)
C10.087 (4)0.052 (3)0.062 (3)0.007 (3)0.006 (3)0.004 (2)
C20.088 (4)0.072 (3)0.062 (3)0.012 (4)0.001 (3)0.003 (3)
C30.051 (3)0.075 (3)0.082 (4)0.007 (3)0.002 (3)0.024 (3)
C40.066 (3)0.051 (3)0.095 (4)0.010 (3)0.007 (3)0.012 (3)
C50.043 (3)0.045 (3)0.067 (3)0.001 (2)0.001 (3)0.005 (2)
C60.065 (3)0.052 (3)0.075 (4)0.021 (3)0.001 (3)0.007 (3)
C70.059 (3)0.060 (3)0.063 (3)0.008 (3)0.004 (3)0.012 (3)
C80.037 (2)0.043 (2)0.057 (3)0.001 (2)0.001 (2)0.008 (2)
C90.034 (2)0.043 (2)0.057 (3)0.002 (2)0.002 (2)0.006 (2)
C100.039 (2)0.042 (2)0.062 (3)0.003 (2)0.005 (2)0.004 (2)
C110.068 (3)0.052 (3)0.054 (3)0.005 (3)0.009 (3)0.003 (2)
C120.064 (3)0.045 (3)0.062 (3)0.007 (3)0.002 (3)0.010 (2)
C130.039 (2)0.045 (2)0.056 (3)0.002 (2)0.002 (2)0.001 (2)
C140.036 (3)0.053 (3)0.052 (3)0.002 (2)0.002 (2)0.008 (2)
C150.068 (4)0.075 (3)0.058 (3)0.013 (3)0.008 (3)0.000 (3)
C160.081 (4)0.072 (3)0.058 (3)0.003 (3)0.012 (3)0.007 (3)
C170.046 (3)0.051 (3)0.067 (3)0.005 (2)0.006 (3)0.004 (2)
C180.031 (2)0.069 (3)0.089 (4)0.002 (3)0.002 (3)0.011 (3)
C190.042 (3)0.072 (3)0.113 (5)0.003 (3)0.006 (3)0.018 (3)
C200.076 (4)0.075 (4)0.082 (4)0.005 (4)0.002 (4)0.012 (3)
C210.096 (5)0.069 (3)0.081 (4)0.017 (4)0.001 (4)0.015 (3)
C220.122 (5)0.079 (4)0.060 (3)0.024 (4)0.027 (4)0.012 (3)
C230.139 (7)0.060 (3)0.087 (4)0.006 (4)0.029 (5)0.017 (3)
C240.137 (7)0.078 (4)0.137 (7)0.043 (5)0.040 (6)0.034 (4)
Geometric parameters (Å, º) top
O1—C201.324 (7)C11—H11A0.9700
O1—C31.443 (6)C11—H11B0.9700
O2—C201.177 (7)C12—C131.521 (6)
O3—C71.220 (6)C12—H12A0.9700
O4—C171.416 (6)C12—H12B0.9700
O4—C231.420 (7)C13—C171.530 (6)
O5—C241.373 (7)C13—C141.546 (6)
O5—C171.439 (6)C13—C181.559 (6)
C1—C21.517 (6)C14—C151.512 (6)
C1—C101.545 (6)C14—H140.9800
C1—H1A0.9700C15—C221.491 (8)
C1—H1B0.9700C15—C161.524 (7)
C2—C31.509 (7)C15—H150.9800
C2—H2A0.9700C16—C221.489 (8)
C2—H2B0.9700C16—C171.502 (7)
C3—C41.488 (7)C16—H160.9800
C3—H30.9800C18—H18A0.9599
C4—C51.506 (7)C18—H18B0.9599
C4—H4A0.9700C18—H18C0.9599
C4—H4B0.9700C19—H19A0.9599
C5—C61.318 (6)C19—H19B0.9599
C5—C101.519 (6)C19—H19C0.9599
C6—C71.451 (7)C20—C211.493 (8)
C6—H60.9300C21—H21A0.9599
C7—C81.503 (6)C21—H21B0.9599
C8—C141.506 (6)C21—H21C0.9599
C8—C91.548 (6)C22—H22A0.9700
C8—H80.9800C22—H22B0.9700
C9—C111.537 (6)C23—C241.488 (10)
C9—C101.555 (6)C23—H23A0.9700
C9—H90.9800C23—H23B0.9700
C10—C191.539 (7)C24—H24A0.9700
C11—C121.527 (6)C24—H24B0.9700
C20—O1—C3117.8 (4)C17—C13—C14101.4 (4)
C17—O4—C23106.7 (5)C12—C13—C18107.8 (4)
C24—O5—C17108.4 (5)C17—C13—C18108.6 (4)
C2—C1—C10115.5 (4)C14—C13—C18116.5 (4)
C2—C1—H1A108.4C8—C14—C15123.3 (4)
C10—C1—H1A108.4C8—C14—C13113.2 (4)
C2—C1—H1B108.4C15—C14—C13106.5 (4)
C10—C1—H1B108.4C8—C14—H14103.9
H1A—C1—H1B107.5C15—C14—H14103.9
C3—C2—C1110.1 (4)C13—C14—H14103.9
C3—C2—H2A109.6C22—C15—C14120.2 (5)
C1—C2—H2A109.6C22—C15—C1659.2 (4)
C3—C2—H2B109.6C14—C15—C16106.2 (4)
C1—C2—H2B109.6C22—C15—H15118.4
H2A—C2—H2B108.2C14—C15—H15118.4
O1—C3—C4107.1 (4)C16—C15—H15118.4
O1—C3—C2111.2 (4)C22—C16—C17121.7 (5)
C4—C3—C2109.7 (5)C22—C16—C1559.3 (4)
O1—C3—H3109.6C17—C16—C15106.9 (4)
C4—C3—H3109.6C22—C16—H16117.8
C2—C3—H3109.6C17—C16—H16117.8
C3—C4—C5112.6 (4)C15—C16—H16117.8
C3—C4—H4A109.1O4—C17—O5104.6 (4)
C5—C4—H4A109.1O4—C17—C16114.6 (4)
C3—C4—H4B109.1O5—C17—C16107.8 (4)
C5—C4—H4B109.1O4—C17—C13113.0 (4)
H4A—C4—H4B107.8O5—C17—C13110.0 (4)
C6—C5—C4121.0 (4)C16—C17—C13106.7 (4)
C6—C5—C10123.0 (4)C13—C18—H18A109.5
C4—C5—C10116.0 (4)C13—C18—H18B109.5
C5—C6—C7123.4 (5)H18A—C18—H18B109.5
C5—C6—H6118.3C13—C18—H18C109.5
C7—C6—H6118.3H18A—C18—H18C109.5
O3—C7—C6120.5 (5)H18B—C18—H18C109.5
O3—C7—C8122.7 (5)C10—C19—H19A109.5
C6—C7—C8116.8 (5)C10—C19—H19B109.5
C7—C8—C14114.4 (4)H19A—C19—H19B109.5
C7—C8—C9105.9 (4)C10—C19—H19C109.5
C14—C8—C9110.2 (3)H19A—C19—H19C109.5
C7—C8—H8108.7H19B—C19—H19C109.5
C14—C8—H8108.7O2—C20—O1122.0 (5)
C9—C8—H8108.7O2—C20—C21125.5 (6)
C11—C9—C8114.3 (4)O1—C20—C21112.5 (6)
C11—C9—C10113.5 (3)C20—C21—H21A109.5
C8—C9—C10112.3 (3)C20—C21—H21B109.5
C11—C9—H9105.2H21A—C21—H21B109.5
C8—C9—H9105.2C20—C21—H21C109.5
C10—C9—H9105.2H21A—C21—H21C109.5
C5—C10—C19108.3 (4)H21B—C21—H21C109.5
C5—C10—C1108.2 (4)C16—C22—C1561.5 (4)
C19—C10—C1110.1 (4)C16—C22—H22A117.6
C5—C10—C9109.6 (4)C15—C22—H22A117.6
C19—C10—C9111.4 (4)C16—C22—H22B117.6
C1—C10—C9109.3 (3)C15—C22—H22B117.6
C12—C11—C9114.3 (4)H22A—C22—H22B114.7
C12—C11—H11A108.7O4—C23—C24104.1 (5)
C9—C11—H11A108.7O4—C23—H23A110.9
C12—C11—H11B108.7C24—C23—H23A110.9
C9—C11—H11B108.7O4—C23—H23B110.9
H11A—C11—H11B107.6C24—C23—H23B110.9
C13—C12—C11110.3 (4)H23A—C23—H23B109.0
C13—C12—H12A109.6O5—C24—C23107.2 (5)
C11—C12—H12A109.6O5—C24—H24A110.3
C13—C12—H12B109.6C23—C24—H24A110.3
C11—C12—H12B109.6O5—C24—H24B110.3
H12A—C12—H12B108.1C23—C24—H24B110.3
C12—C13—C17116.9 (4)H24A—C24—H24B108.5
C12—C13—C14105.9 (4)
C10—C1—C2—C355.7 (7)C7—C8—C14—C13175.0 (4)
C20—O1—C3—C4141.1 (5)C9—C8—C14—C1355.9 (5)
C20—O1—C3—C299.1 (6)C12—C13—C14—C865.7 (5)
C1—C2—C3—O1176.3 (5)C17—C13—C14—C8171.7 (4)
C1—C2—C3—C458.1 (6)C18—C13—C14—C854.1 (6)
O1—C3—C4—C5178.0 (5)C12—C13—C14—C15155.7 (4)
C2—C3—C4—C557.2 (6)C17—C13—C14—C1533.1 (5)
C3—C4—C5—C6125.8 (5)C18—C13—C14—C1584.6 (5)
C3—C4—C5—C1053.0 (6)C8—C14—C15—C2290.2 (6)
C4—C5—C6—C7179.4 (5)C13—C14—C15—C2243.2 (6)
C10—C5—C6—C71.9 (8)C8—C14—C15—C16153.5 (5)
C5—C6—C7—O3165.2 (5)C13—C14—C15—C1620.2 (5)
C5—C6—C7—C815.3 (8)C14—C15—C16—C22115.9 (5)
O3—C7—C8—C1413.8 (7)C22—C15—C16—C17117.3 (5)
C6—C7—C8—C14166.7 (4)C14—C15—C16—C171.3 (6)
O3—C7—C8—C9135.4 (5)C23—O4—C17—O530.7 (5)
C6—C7—C8—C945.1 (5)C23—O4—C17—C1687.1 (5)
C7—C8—C9—C11167.3 (4)C23—O4—C17—C13150.3 (4)
C14—C8—C9—C1143.1 (5)C24—O5—C17—O423.0 (6)
C7—C8—C9—C1061.5 (5)C24—O5—C17—C1699.4 (6)
C14—C8—C9—C10174.3 (4)C24—O5—C17—C13144.7 (5)
C6—C5—C10—C19107.5 (6)C22—C16—C17—O484.6 (6)
C4—C5—C10—C1973.7 (5)C15—C16—C17—O4148.5 (4)
C6—C5—C10—C1133.2 (5)C22—C16—C17—O5159.4 (5)
C4—C5—C10—C145.6 (6)C15—C16—C17—O595.5 (5)
C6—C5—C10—C914.2 (6)C22—C16—C17—C1341.3 (6)
C4—C5—C10—C9164.6 (4)C15—C16—C17—C1322.6 (6)
C2—C1—C10—C547.7 (6)C12—C13—C17—O484.6 (5)
C2—C1—C10—C1970.5 (6)C14—C13—C17—O4160.8 (4)
C2—C1—C10—C9166.9 (5)C18—C13—C17—O437.6 (5)
C11—C9—C10—C5178.1 (4)C12—C13—C17—O531.9 (6)
C8—C9—C10—C546.6 (5)C14—C13—C17—O582.7 (4)
C11—C9—C10—C1958.3 (5)C18—C13—C17—O5154.1 (4)
C8—C9—C10—C1973.2 (5)C12—C13—C17—C16148.6 (4)
C11—C9—C10—C163.5 (5)C14—C13—C17—C1634.0 (5)
C8—C9—C10—C1165.0 (4)C18—C13—C17—C1689.2 (5)
C8—C9—C11—C1243.1 (6)C3—O1—C20—O20.9 (9)
C10—C9—C11—C12173.7 (4)C3—O1—C20—C21178.4 (5)
C9—C11—C12—C1353.3 (6)C17—C16—C22—C1591.7 (5)
C11—C12—C13—C17173.8 (4)C14—C15—C22—C1691.6 (5)
C11—C12—C13—C1461.7 (5)C17—O4—C23—C2426.4 (7)
C11—C12—C13—C1863.6 (5)C17—O5—C24—C236.7 (8)
C7—C8—C14—C1554.3 (6)O4—C23—C24—O512.1 (8)
C9—C8—C14—C15173.5 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C3—H3···O20.982.262.635 (8)101
C15—H15···O30.982.542.949 (7)105
C23—H23A···O3i0.972.403.333 (8)162
Symmetry code: (i) x+1, y+1/2, z+3/2.
 

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