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The title compound, C21H24O2, contains four rings. The cyclo­hexa­dienone ring is planar, the cyclo­hexane and cyclo­hexene rings adopt chair and sofa conformations, respectively, while the cyclo­pentene ring adopts an envelope conformation. Weak inter­molecular C—H...O hydrogen bonding helps to stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806046514/xu2130sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806046514/xu2130Isup2.hkl
Contains datablock I

CCDC reference: 630511

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.039
  • wR factor = 0.124
  • Data-to-parameter ratio = 10.7

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated . !
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 27.40 From the CIF: _reflns_number_total 2267 Count of symmetry unique reflns 2261 Completeness (_total/calc) 100.27% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 6 Fraction of Friedel pairs measured 0.003 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 C8 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C13 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C14 = . R
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 7 ALERT level G = General alerts; check 6 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 0 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: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia,1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Pregna-1,4,9(11),16-tetraene-3,20-dione top
Crystal data top
C21H24O2F(000) = 664
Mr = 308.40Dx = 1.191 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 12671 reflections
a = 6.6433 (19) Åθ = 3.2–27.5°
b = 11.278 (4) ŵ = 0.08 mm1
c = 22.951 (8) ÅT = 293 K
V = 1719.6 (10) Å3Chunk, colorless
Z = 40.42 × 0.36 × 0.32 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1393 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.036
Graphite monochromatorθmax = 27.4°, θmin = 3.1°
Detector resolution: 10.00 pixels mm-1h = 88
ω scansk = 1414
17000 measured reflectionsl = 2729
2267 independent reflections
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)] = 0.039H-atom parameters constrained
wR(F2) = 0.124 w = 1/[σ2(Fo2) + (0.055P)2 + 0.1715P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max = 0.001
2267 reflectionsΔρmax = 0.14 e Å3
212 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (3)
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
O10.4852 (4)0.9160 (3)0.01135 (9)0.1169 (9)
O20.7845 (4)0.7254 (2)0.41831 (10)0.0966 (8)
C10.5076 (5)0.7236 (3)0.11068 (13)0.0802 (9)
H10.58510.66020.12370.096*
C20.5583 (5)0.7737 (4)0.06033 (13)0.0918 (11)
H20.66800.74440.03970.110*
C30.4459 (5)0.8732 (3)0.03691 (13)0.0826 (10)
C40.2849 (5)0.9187 (3)0.07242 (11)0.0748 (8)
H40.21580.98570.05980.090*
C50.2308 (4)0.8687 (2)0.12273 (11)0.0627 (7)
C60.0610 (5)0.9184 (3)0.15841 (11)0.0797 (9)
H6A0.04930.86200.15930.096*
H6B0.01250.99090.14060.096*
C70.1307 (5)0.9440 (3)0.22043 (11)0.0725 (8)
H7A0.01520.96730.24360.087*
H7B0.22361.01040.21970.087*
C80.2337 (4)0.8383 (2)0.24965 (10)0.0559 (6)
H80.13320.77640.25670.067*
C90.3984 (4)0.7883 (2)0.21085 (10)0.0548 (6)
C100.3353 (4)0.7620 (2)0.14763 (11)0.0602 (7)
C110.5823 (4)0.7677 (2)0.23091 (11)0.0628 (7)
H110.67830.74410.20380.075*
C120.6513 (4)0.7789 (3)0.29318 (11)0.0646 (7)
H12A0.73030.85060.29780.077*
H12B0.73570.71180.30330.077*
C130.4698 (4)0.7830 (2)0.33342 (11)0.0564 (6)
C140.3255 (4)0.8749 (2)0.30746 (10)0.0561 (6)
H140.40870.94450.29880.067*
C150.1915 (4)0.9116 (3)0.35889 (10)0.0750 (8)
H15A0.14340.99240.35480.090*
H15B0.07770.85850.36360.090*
C160.3388 (5)0.8997 (3)0.40807 (12)0.0734 (8)
H160.32150.93520.44430.088*
C170.4965 (4)0.8331 (2)0.39434 (11)0.0618 (7)
C180.3747 (5)0.6592 (2)0.33910 (12)0.0712 (8)
H18A0.46040.60950.36230.107*
H18B0.35900.62490.30110.107*
H18C0.24540.66590.35750.107*
C190.1861 (6)0.6556 (3)0.14813 (12)0.0845 (9)
H19A0.07520.67330.17350.127*
H19B0.25430.58590.16190.127*
H19C0.13700.64200.10940.127*
C200.6632 (5)0.8013 (3)0.43314 (12)0.0708 (8)
C210.6834 (6)0.8645 (3)0.49060 (12)0.0943 (11)
H21A0.80080.83610.51060.141*
H21B0.56620.84950.51390.141*
H21C0.69600.94820.48390.141*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.141 (2)0.144 (2)0.0650 (12)0.033 (2)0.0217 (15)0.0112 (14)
O20.0909 (15)0.1037 (18)0.0952 (15)0.0217 (15)0.0220 (14)0.0002 (14)
C10.088 (2)0.086 (2)0.0671 (17)0.016 (2)0.0038 (17)0.0126 (16)
C20.086 (2)0.122 (3)0.0675 (18)0.000 (2)0.0159 (18)0.021 (2)
C30.095 (2)0.095 (2)0.0583 (16)0.025 (2)0.0088 (17)0.0014 (16)
C40.095 (2)0.0696 (18)0.0602 (16)0.0069 (18)0.0014 (16)0.0056 (14)
C50.0662 (16)0.0642 (17)0.0576 (14)0.0036 (14)0.0029 (13)0.0026 (12)
C60.0735 (18)0.095 (2)0.0703 (17)0.0206 (18)0.0008 (15)0.0132 (16)
C70.0714 (17)0.0791 (19)0.0671 (15)0.0189 (16)0.0062 (14)0.0061 (14)
C80.0503 (13)0.0561 (15)0.0612 (14)0.0026 (12)0.0051 (11)0.0043 (11)
C90.0562 (14)0.0508 (14)0.0575 (13)0.0027 (12)0.0067 (12)0.0012 (11)
C100.0632 (14)0.0580 (15)0.0595 (14)0.0026 (14)0.0037 (13)0.0012 (12)
C110.0539 (14)0.0694 (17)0.0650 (15)0.0024 (14)0.0087 (13)0.0038 (13)
C120.0530 (14)0.0700 (17)0.0707 (16)0.0022 (14)0.0010 (13)0.0034 (14)
C130.0529 (14)0.0549 (14)0.0616 (14)0.0007 (12)0.0011 (12)0.0006 (12)
C140.0554 (14)0.0573 (15)0.0558 (13)0.0034 (13)0.0061 (11)0.0025 (11)
C150.0705 (16)0.088 (2)0.0663 (16)0.0170 (17)0.0068 (15)0.0063 (16)
C160.0816 (19)0.082 (2)0.0572 (14)0.0050 (18)0.0025 (15)0.0068 (14)
C170.0623 (15)0.0634 (16)0.0596 (14)0.0023 (15)0.0009 (13)0.0028 (13)
C180.0797 (18)0.0573 (16)0.0765 (17)0.0097 (15)0.0049 (16)0.0080 (13)
C190.109 (2)0.0687 (19)0.0760 (18)0.0273 (19)0.0120 (19)0.0044 (15)
C200.0722 (17)0.0711 (19)0.0691 (17)0.0077 (17)0.0046 (15)0.0062 (15)
C210.099 (2)0.113 (3)0.0701 (17)0.015 (2)0.0153 (19)0.0038 (18)
Geometric parameters (Å, º) top
O1—C31.236 (3)C11—H110.9300
O2—C201.224 (4)C12—C131.519 (4)
C1—C21.330 (4)C12—H12A0.9700
C1—C101.489 (4)C12—H12B0.9700
C1—H10.9300C13—C171.518 (4)
C2—C31.451 (5)C13—C141.532 (3)
C2—H20.9300C13—C181.539 (4)
C3—C41.440 (4)C14—C151.535 (3)
C4—C51.334 (4)C14—H140.9800
C4—H40.9300C15—C161.500 (4)
C5—C101.502 (4)C15—H15A0.9700
C5—C61.502 (4)C15—H15B0.9700
C6—C71.525 (4)C16—C171.327 (4)
C6—H6A0.9700C16—H160.9300
C6—H6B0.9700C17—C201.466 (4)
C7—C81.530 (4)C18—H18A0.9600
C7—H7A0.9700C18—H18B0.9600
C7—H7B0.9700C18—H18C0.9600
C8—C141.517 (3)C19—H19A0.9600
C8—C91.519 (3)C19—H19B0.9600
C8—H80.9800C19—H19C0.9600
C9—C111.326 (4)C20—C211.505 (4)
C9—C101.539 (3)C21—H21A0.9600
C10—C191.556 (4)C21—H21B0.9600
C11—C121.506 (4)C21—H21C0.9600
C2—C1—C10124.5 (3)C11—C12—H12B109.7
C2—C1—H1117.8C13—C12—H12B109.7
C10—C1—H1117.8H12A—C12—H12B108.2
C1—C2—C3121.4 (3)C17—C13—C12118.6 (2)
C1—C2—H2119.3C17—C13—C14100.3 (2)
C3—C2—H2119.3C12—C13—C14106.33 (19)
O1—C3—C4121.7 (4)C17—C13—C18107.9 (2)
O1—C3—C2121.7 (3)C12—C13—C18110.5 (2)
C4—C3—C2116.6 (3)C14—C13—C18112.9 (2)
C5—C4—C3122.6 (3)C8—C14—C13114.1 (2)
C5—C4—H4118.7C8—C14—C15120.8 (2)
C3—C4—H4118.7C13—C14—C15104.25 (19)
C4—C5—C10122.9 (3)C8—C14—H14105.5
C4—C5—C6121.1 (3)C13—C14—H14105.5
C10—C5—C6116.0 (2)C15—C14—H14105.5
C5—C6—C7110.6 (2)C16—C15—C14100.2 (2)
C5—C6—H6A109.5C16—C15—H15A111.7
C7—C6—H6A109.5C14—C15—H15A111.7
C5—C6—H6B109.5C16—C15—H15B111.7
C7—C6—H6B109.5C14—C15—H15B111.7
H6A—C6—H6B108.1H15A—C15—H15B109.5
C6—C7—C8113.4 (2)C17—C16—C15112.8 (2)
C6—C7—H7A108.9C17—C16—H16123.6
C8—C7—H7A108.9C15—C16—H16123.6
C6—C7—H7B108.9C16—C17—C20126.2 (3)
C8—C7—H7B108.9C16—C17—C13109.7 (2)
H7A—C7—H7B107.7C20—C17—C13123.8 (3)
C14—C8—C9108.9 (2)C13—C18—H18A109.5
C14—C8—C7110.6 (2)C13—C18—H18B109.5
C9—C8—C7110.8 (2)H18A—C18—H18B109.5
C14—C8—H8108.9C13—C18—H18C109.5
C9—C8—H8108.9H18A—C18—H18C109.5
C7—C8—H8108.9H18B—C18—H18C109.5
C11—C9—C8121.7 (2)C10—C19—H19A109.5
C11—C9—C10123.0 (2)C10—C19—H19B109.5
C8—C9—C10115.3 (2)H19A—C19—H19B109.5
C1—C10—C5111.8 (2)C10—C19—H19C109.5
C1—C10—C9112.5 (2)H19A—C19—H19C109.5
C5—C10—C9109.3 (2)H19B—C19—H19C109.5
C1—C10—C19105.7 (2)O2—C20—C17120.0 (3)
C5—C10—C19109.0 (2)O2—C20—C21121.1 (3)
C9—C10—C19108.4 (2)C17—C20—C21118.9 (3)
C9—C11—C12126.5 (2)C20—C21—H21A109.5
C9—C11—H11116.7C20—C21—H21B109.5
C12—C11—H11116.7H21A—C21—H21B109.5
C11—C12—C13109.7 (2)C20—C21—H21C109.5
C11—C12—H12A109.7H21A—C21—H21C109.5
C13—C12—H12A109.7H21B—C21—H21C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C19—H19C···O1i0.962.553.505 (4)173
C21—H21B···O2ii0.962.583.524 (5)170
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x1/2, y+3/2, z+1.
 

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