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The title compound, C18H21FO2, (I), is a steroid with a dienone structure and six stereogenic centers. These steroids are substrates for estradiol derivatives with an alkyl chain in the 7α-position [Krause & Thorand (1999). Inorg. Chim. Acta. 296, 1–11; Uerdingen & Krause (2000). Tetrahedron, 56, 2799–2804]. The configuration of the 11-position is S. The diene is in conjugation with the carbonyl group and the latter is involved in a weak intermolecular C—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801000484/ci6002sup1.cif
Contains datablocks I, ccd1385

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536801000484/ci6002Isup2.hkl
Contains datablock I

CCDC reference: 159718

Key indicators

  • Single-crystal X-ray study
  • T = 291 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.042
  • wR factor = 0.096
  • Data-to-parameter ratio = 7.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


Yellow Alert Alert Level C:
STRVAL_01 From the CIF: _refine_ls_abs_structure_Flack -0.800 From the CIF: _refine_ls_abs_structure_Flack_su 1.600 Alert C Flack parameter is too small General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 25.34 From the CIF: _reflns_number_total 1409 Count of symmetry unique reflns 1482 Completeness (_total/calc) 95.07% 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 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.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check

Comment top

NO COMMENT

Experimental top

The title compound, (I), was obtained with 80–90% yield through bromination and dehydrobromination from 3-acetyl-11-fluoroandrosta-4,6-dien-17-one (Vettel, 1998). It was dissolved in a small amount of dichloromethane and cyclohexane, and crystals were obtained by vapour diffusion.

Refinement top

H atoms were placed in calculated positions with Uiso constrained to be 1.5Ueq of the carrier atom for the methyl groups and 1.2Ueq for the remaining positions. The absolute structure could not be determined reliably and the Friedel reflections were merged before final refinement because of the large s.u. for the Flack parameter [-0.8 (16)].

Computing details top

Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97 and PARST95 (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. The structure of (I) showing 50% probability displacement ellipsoids and the atom-numbering scheme; one of the H atoms attached to C15 is hidden.
(I) top
Crystal data top
C18H21FO2F(000) = 308
Mr = 288.35Dx = 1.288 Mg m3
Monoclinic, P21Mo Kα radiation, λ = 0.71073 Å
a = 9.4058 (5) ÅCell parameters from 3898 reflections
b = 7.7654 (4) Åθ = 3.3–25.3°
c = 10.2125 (6) ŵ = 0.09 mm1
β = 94.349 (3)°T = 291 K
V = 743.77 (7) Å3Plate, colourless
Z = 20.35 × 0.30 × 0.05 mm
Data collection top
Nonius KappaCCD
diffractometer
876 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.042
Graphite monochromatorθmax = 25.3°, θmin = 3.3°
Detector resolution: 10 vertical, 18 horizontal pixels mm-1h = 1111
206 frames via ω–rotation (Δω=1%) at different κ–angles and two times 60 s per frame scansk = 09
3898 measured reflectionsl = 012
1409 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)] = 0.042H-atom parameters constrained
wR(F2) = 0.096 w = 1/[σ2(Fo2) + (0.0429P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.99(Δ/σ)max < 0.001
1409 reflectionsΔρmax = 0.11 e Å3
190 parametersΔρmin = 0.14 e Å3
1 restraintAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.8 (16)
Crystal data top
C18H21FO2V = 743.77 (7) Å3
Mr = 288.35Z = 2
Monoclinic, P21Mo Kα radiation
a = 9.4058 (5) ŵ = 0.09 mm1
b = 7.7654 (4) ÅT = 291 K
c = 10.2125 (6) Å0.35 × 0.30 × 0.05 mm
β = 94.349 (3)°
Data collection top
Nonius KappaCCD
diffractometer
876 reflections with I > 2σ(I)
3898 measured reflectionsRint = 0.042
1409 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.042H-atom parameters constrained
wR(F2) = 0.096Δρmax = 0.11 e Å3
S = 0.99Δρmin = 0.14 e Å3
1409 reflectionsAbsolute structure: Flack (1983)
190 parametersAbsolute structure parameter: 0.8 (16)
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
xyzUiso*/Ueq
F10.5391 (2)0.2418 (4)0.6004 (2)0.0947 (9)
O10.0109 (4)0.3391 (5)0.9978 (4)0.1056 (11)
O21.0462 (2)0.4745 (4)0.6286 (2)0.0814 (10)
C10.3359 (3)0.2215 (6)0.8491 (3)0.0584 (10)
H1A0.38920.20690.93340.070*
H1B0.36430.13060.79140.070*
C20.1765 (3)0.2049 (5)0.8670 (4)0.0642 (11)
H2A0.12450.19880.78140.077*
H2B0.15960.09870.91330.077*
C30.1217 (4)0.3532 (6)0.9420 (3)0.0683 (12)
C40.1963 (4)0.5148 (6)0.9382 (3)0.0588 (10)
H4A0.16490.60610.98740.071*
C50.3089 (3)0.5403 (5)0.8671 (3)0.0489 (9)
C60.3690 (3)0.7099 (5)0.8550 (3)0.0586 (11)
H6A0.32780.80130.89710.070*
C70.4800 (4)0.7414 (5)0.7867 (3)0.0595 (10)
H7A0.51080.85470.78010.071*
C80.5585 (3)0.6031 (5)0.7197 (3)0.0489 (9)
H8A0.51940.59730.62810.059*
C90.5331 (3)0.4285 (5)0.7837 (3)0.0450 (9)
H9A0.57410.43730.87460.054*
C100.3730 (3)0.3956 (5)0.7914 (3)0.0460 (9)
H10A0.32860.39970.70150.055*
C110.6114 (3)0.2810 (5)0.7214 (4)0.0603 (10)
H11A0.60790.17980.77850.072*
C120.7677 (4)0.3185 (5)0.6999 (4)0.0617 (10)
H12A0.82360.31210.78350.074*
H12B0.80270.23060.64300.074*
C130.7888 (3)0.4934 (5)0.6394 (3)0.0504 (10)
C140.7183 (3)0.6309 (5)0.7200 (3)0.0496 (9)
H14A0.75640.61390.81100.060*
C150.7808 (4)0.8016 (6)0.6759 (4)0.0777 (13)
H15A0.77260.89100.74130.093*
H15B0.73480.83980.59280.093*
C160.9378 (4)0.7524 (7)0.6625 (4)0.0852 (14)
H16A0.97400.81120.58820.102*
H16B0.99610.78400.74130.102*
C170.9409 (4)0.5606 (7)0.6425 (3)0.0639 (11)
C180.7380 (3)0.4975 (7)0.4917 (3)0.0828 (15)
H18A0.75250.61070.45730.124*
H18B0.63850.46900.48090.124*
H18C0.79160.41530.44520.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0588 (12)0.109 (2)0.1170 (17)0.0086 (14)0.0121 (11)0.0693 (17)
O10.0908 (19)0.102 (3)0.132 (2)0.019 (2)0.0631 (16)0.009 (2)
O20.0479 (14)0.114 (3)0.0829 (16)0.0106 (17)0.0068 (11)0.0023 (17)
C10.055 (2)0.047 (3)0.074 (2)0.004 (2)0.0058 (17)0.000 (2)
C20.057 (2)0.055 (3)0.082 (2)0.009 (2)0.0128 (18)0.008 (2)
C30.063 (2)0.079 (4)0.064 (2)0.001 (3)0.0176 (18)0.000 (2)
C40.059 (2)0.055 (3)0.063 (2)0.003 (2)0.0140 (17)0.0066 (19)
C50.0477 (19)0.050 (3)0.0487 (18)0.0040 (19)0.0004 (15)0.0009 (17)
C60.066 (2)0.042 (3)0.070 (2)0.006 (2)0.0178 (19)0.005 (2)
C70.064 (2)0.034 (2)0.082 (3)0.004 (2)0.0132 (19)0.004 (2)
C80.050 (2)0.046 (3)0.0508 (18)0.0034 (19)0.0040 (14)0.0039 (18)
C90.0473 (19)0.039 (3)0.0487 (18)0.0021 (17)0.0029 (14)0.0032 (16)
C100.0440 (19)0.042 (3)0.0517 (18)0.0012 (17)0.0055 (14)0.0015 (18)
C110.049 (2)0.048 (3)0.084 (3)0.0005 (19)0.0055 (18)0.011 (2)
C120.049 (2)0.049 (3)0.088 (3)0.0054 (19)0.0082 (17)0.008 (2)
C130.0407 (18)0.061 (3)0.0488 (18)0.004 (2)0.0019 (14)0.0020 (19)
C140.054 (2)0.043 (3)0.0530 (19)0.0043 (19)0.0057 (15)0.0074 (18)
C150.073 (3)0.065 (3)0.098 (3)0.004 (2)0.019 (2)0.017 (2)
C160.067 (3)0.087 (4)0.104 (3)0.015 (3)0.021 (2)0.024 (3)
C170.053 (2)0.087 (4)0.051 (2)0.004 (2)0.0027 (16)0.013 (2)
C180.057 (2)0.134 (5)0.057 (2)0.013 (3)0.0026 (16)0.008 (3)
Geometric parameters (Å, º) top
F1—C111.399 (4)C9—C101.535 (4)
O1—C31.230 (4)C9—H9A0.9800
O2—C171.212 (4)C10—H10A0.9800
C1—C101.526 (5)C11—C121.530 (4)
C1—C21.529 (4)C11—H11A0.9800
C1—H1A0.9700C12—C131.512 (5)
C1—H1B0.9700C12—H12A0.9700
C2—C31.496 (5)C12—H12B0.9700
C2—H2A0.9700C13—C171.521 (5)
C2—H2B0.9700C13—C141.530 (5)
C3—C41.440 (6)C13—C181.548 (4)
C4—C51.344 (4)C14—C151.532 (6)
C4—H4A0.9300C14—H14A0.9800
C5—C61.442 (5)C15—C161.541 (5)
C5—C101.515 (5)C15—H15A0.9700
C6—C71.321 (4)C15—H15B0.9700
C6—H6A0.9300C16—C171.503 (7)
C7—C81.498 (5)C16—H16A0.9700
C7—H7A0.9300C16—H16B0.9700
C8—C141.518 (4)C18—H18A0.9600
C8—C91.532 (5)C18—H18B0.9600
C8—H8A0.9800C18—H18C0.9600
C9—C111.526 (5)
C10—C1—C2112.1 (3)F1—C11—C9108.3 (3)
C10—C1—H1A109.2F1—C11—C12108.8 (3)
C2—C1—H1A109.2C9—C11—C12114.6 (3)
C10—C1—H1B109.2F1—C11—H11A108.3
C2—C1—H1B109.2C9—C11—H11A108.3
H1A—C1—H1B107.9C12—C11—H11A108.3
C3—C2—C1112.1 (3)C13—C12—C11112.8 (3)
C3—C2—H2A109.2C13—C12—H12A109.0
C1—C2—H2A109.2C11—C12—H12A109.0
C3—C2—H2B109.2C13—C12—H12B109.0
C1—C2—H2B109.2C11—C12—H12B109.0
H2A—C2—H2B107.9H12A—C12—H12B107.8
O1—C3—C4121.4 (4)C12—C13—C17116.9 (3)
O1—C3—C2120.4 (4)C12—C13—C14109.3 (2)
C4—C3—C2118.0 (3)C17—C13—C14101.3 (3)
C5—C4—C3123.3 (4)C12—C13—C18112.1 (3)
C5—C4—H4A118.4C17—C13—C18103.5 (2)
C3—C4—H4A118.4C14—C13—C18113.3 (3)
C4—C5—C6120.8 (3)C8—C14—C13111.7 (3)
C4—C5—C10121.8 (3)C8—C14—C15121.6 (3)
C6—C5—C10117.4 (3)C13—C14—C15104.7 (3)
C7—C6—C5123.0 (4)C8—C14—H14A105.9
C7—C6—H6A118.5C13—C14—H14A105.9
C5—C6—H6A118.5C15—C14—H14A105.9
C6—C7—C8123.0 (4)C14—C15—C16101.7 (3)
C6—C7—H7A118.5C14—C15—H15A111.4
C8—C7—H7A118.5C16—C15—H15A111.4
C7—C8—C14114.8 (3)C14—C15—H15B111.4
C7—C8—C9110.0 (2)C16—C15—H15B111.4
C14—C8—C9108.1 (3)H15A—C15—H15B109.3
C7—C8—H8A107.9C17—C16—C15106.7 (4)
C14—C8—H8A107.9C17—C16—H16A110.4
C9—C8—H8A107.9C15—C16—H16A110.4
C11—C9—C8113.0 (2)C17—C16—H16B110.4
C11—C9—C10113.7 (3)C15—C16—H16B110.4
C8—C9—C10110.7 (3)H16A—C16—H16B108.6
C11—C9—H9A106.2O2—C17—C16125.9 (4)
C8—C9—H9A106.2O2—C17—C13125.7 (5)
C10—C9—H9A106.2C16—C17—C13108.3 (3)
C5—C10—C1110.4 (2)C13—C18—H18A109.5
C5—C10—C9109.4 (3)C13—C18—H18B109.5
C1—C10—C9114.9 (3)H18A—C18—H18B109.5
C5—C10—H10A107.3C13—C18—H18C109.5
C1—C10—H10A107.3H18A—C18—H18C109.5
C9—C10—H10A107.3H18B—C18—H18C109.5
C10—C1—C2—C352.1 (4)C8—C9—C11—C1246.6 (4)
C1—C2—C3—O1158.9 (4)C10—C9—C11—C12174.0 (3)
C1—C2—C3—C425.8 (5)F1—C11—C12—C1375.4 (4)
O1—C3—C4—C5172.8 (4)C9—C11—C12—C1346.0 (4)
C2—C3—C4—C52.5 (5)C11—C12—C13—C17166.4 (3)
C3—C4—C5—C6172.8 (3)C11—C12—C13—C1452.2 (4)
C3—C4—C5—C104.1 (5)C11—C12—C13—C1874.4 (3)
C4—C5—C6—C7179.7 (3)C7—C8—C14—C13174.9 (3)
C10—C5—C6—C73.3 (5)C9—C8—C14—C1362.0 (3)
C5—C6—C7—C82.6 (5)C7—C8—C14—C1550.4 (4)
C6—C7—C8—C14144.4 (3)C9—C8—C14—C15173.5 (3)
C6—C7—C8—C922.2 (4)C12—C13—C14—C862.1 (3)
C7—C8—C9—C11179.3 (3)C17—C13—C14—C8173.9 (3)
C14—C8—C9—C1153.3 (3)C18—C13—C14—C863.7 (4)
C7—C8—C9—C1051.8 (3)C12—C13—C14—C15164.4 (3)
C14—C8—C9—C10177.8 (3)C17—C13—C14—C1540.4 (3)
C4—C5—C10—C122.5 (4)C18—C13—C14—C1569.8 (4)
C6—C5—C10—C1160.5 (3)C8—C14—C15—C16167.2 (3)
C4—C5—C10—C9149.9 (3)C13—C14—C15—C1639.6 (4)
C6—C5—C10—C933.1 (4)C14—C15—C16—C1723.0 (4)
C2—C1—C10—C549.7 (4)C15—C16—C17—O2179.6 (3)
C2—C1—C10—C9174.1 (3)C15—C16—C17—C131.7 (4)
C11—C9—C10—C5174.1 (3)C12—C13—C17—O237.0 (5)
C8—C9—C10—C557.4 (3)C14—C13—C17—O2155.7 (3)
C11—C9—C10—C149.3 (4)C18—C13—C17—O286.8 (4)
C8—C9—C10—C1177.8 (3)C12—C13—C17—C16144.3 (3)
C8—C9—C11—F175.0 (3)C14—C13—C17—C1625.6 (4)
C10—C9—C11—F152.4 (4)C18—C13—C17—C1691.9 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O1i0.932.463.280 (5)147
Symmetry code: (i) x, y+1/2, z+2.

Experimental details

Crystal data
Chemical formulaC18H21FO2
Mr288.35
Crystal system, space groupMonoclinic, P21
Temperature (K)291
a, b, c (Å)9.4058 (5), 7.7654 (4), 10.2125 (6)
β (°) 94.349 (3)
V3)743.77 (7)
Z2
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.35 × 0.30 × 0.05
Data collection
DiffractometerNonius KappaCCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3898, 1409, 876
Rint0.042
(sin θ/λ)max1)0.602
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.042, 0.096, 0.99
No. of reflections1409
No. of parameters190
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.11, 0.14
Absolute structureFlack (1983)
Absolute structure parameter0.8 (16)

Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1991), SHELXL97 and PARST95 (Nardelli, 1995).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C4—H4A···O1i0.932.463.280 (5)147
Symmetry code: (i) x, y+1/2, z+2.
 

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