Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057315/is2235sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057315/is2235Isup2.hkl |
CCDC reference: 672935
The title compound was synthesized according to the literature method (Bittler et al., 1984). Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation from a tetrahydrofuran solution.
C-bound H atoms were placed at calculated positions (C—H = 0.93–0.98 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C). The hydroxy H atoms were located in a difference map and refined isotropically with restraint O—H = 0.84 (2) Å. Owing to negligible anomalous scattering effects, Friedel pairs were averaged in the refinement. The absolute stereochemistry of (I) was known from the synthetic route (Bittler et al., 1984).
Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); 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).
C20H28O3 | F(000) = 344 |
Mr = 316.42 | Dx = 1.249 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2477 reflections |
a = 6.5158 (9) Å | θ = 3.3–27.4° |
b = 20.592 (3) Å | µ = 0.08 mm−1 |
c = 6.5877 (9) Å | T = 296 K |
β = 107.837 (2)° | Prism, colorless |
V = 841.4 (2) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 2 |
Bruker APEXII CCD area-detector diffractometer | 1884 independent reflections |
Radiation source: fine-focus sealed tube | 1739 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
ϕ and ω scans | θmax = 27.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −7→8 |
Tmin = 0.976, Tmax = 0.984 | k = −26→26 |
5279 measured reflections | l = −8→6 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0707P)2 + 0.0701P] where P = (Fo2 + 2Fc2)/3 |
1884 reflections | (Δ/σ)max < 0.001 |
216 parameters | Δρmax = 0.19 e Å−3 |
3 restraints | Δρmin = −0.17 e Å−3 |
C20H28O3 | V = 841.4 (2) Å3 |
Mr = 316.42 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 6.5158 (9) Å | µ = 0.08 mm−1 |
b = 20.592 (3) Å | T = 296 K |
c = 6.5877 (9) Å | 0.30 × 0.20 × 0.20 mm |
β = 107.837 (2)° |
Bruker APEXII CCD area-detector diffractometer | 1884 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 1739 reflections with I > 2σ(I) |
Tmin = 0.976, Tmax = 0.984 | Rint = 0.021 |
5279 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | 3 restraints |
wR(F2) = 0.110 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.19 e Å−3 |
1884 reflections | Δρmin = −0.17 e Å−3 |
216 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.0158 (4) | 0.57314 (9) | −0.3266 (3) | 0.0552 (5) | |
H1X | −0.091 (4) | 0.5628 (18) | −0.416 (4) | 0.062 (10)* | |
O2 | 0.0413 (3) | 0.64237 (9) | 0.0343 (3) | 0.0509 (5) | |
H2X | 0.030 (10) | 0.609 (2) | −0.044 (9) | 0.15 (2)* | |
O3 | 0.3570 (3) | 1.03434 (11) | −0.3503 (3) | 0.0623 (5) | |
C1 | −0.1688 (4) | 0.70794 (12) | −0.3885 (4) | 0.0431 (5) | |
H1A | −0.2548 | 0.6747 | −0.3486 | 0.052* | |
H1B | −0.2674 | 0.7396 | −0.4758 | 0.052* | |
C2 | −0.0437 (5) | 0.67689 (12) | −0.5215 (4) | 0.0496 (6) | |
H2A | 0.0307 | 0.7103 | −0.5754 | 0.060* | |
H2B | −0.1430 | 0.6551 | −0.6427 | 0.060* | |
C3 | 0.1197 (5) | 0.62810 (12) | −0.3921 (4) | 0.0494 (6) | |
H3 | 0.2077 | 0.6124 | −0.4788 | 0.059* | |
C4 | 0.2652 (4) | 0.65956 (11) | −0.1923 (4) | 0.0443 (5) | |
H4A | 0.3543 | 0.6917 | −0.2326 | 0.053* | |
H4B | 0.3602 | 0.6267 | −0.1074 | 0.053* | |
C5 | 0.1422 (4) | 0.69255 (10) | −0.0546 (3) | 0.0364 (5) | |
C6 | 0.3031 (4) | 0.72557 (12) | 0.1315 (4) | 0.0428 (5) | |
H6 | 0.3837 | 0.6995 | 0.2428 | 0.051* | |
C7 | 0.3376 (4) | 0.78913 (12) | 0.1477 (4) | 0.0427 (5) | |
H7 | 0.4451 | 0.8048 | 0.2656 | 0.051* | |
C8 | 0.2114 (3) | 0.83711 (10) | −0.0151 (3) | 0.0342 (4) | |
H8 | 0.1020 | 0.8569 | 0.0394 | 0.041* | |
C9 | 0.0945 (3) | 0.80199 (10) | −0.2272 (3) | 0.0331 (4) | |
H9 | 0.2088 | 0.7847 | −0.2801 | 0.040* | |
C10 | −0.0304 (3) | 0.74189 (10) | −0.1847 (3) | 0.0340 (4) | |
C11 | −0.0357 (4) | 0.84930 (12) | −0.4003 (4) | 0.0448 (5) | |
H11A | −0.1603 | 0.8642 | −0.3622 | 0.054* | |
H11B | −0.0878 | 0.8262 | −0.5346 | 0.054* | |
C12 | 0.0961 (4) | 0.90909 (12) | −0.4311 (4) | 0.0462 (6) | |
H12A | 0.2075 | 0.8954 | −0.4915 | 0.055* | |
H12B | 0.0022 | 0.9395 | −0.5291 | 0.055* | |
C13 | 0.1993 (3) | 0.94225 (10) | −0.2162 (4) | 0.0369 (5) | |
C14 | 0.3449 (3) | 0.89105 (10) | −0.0685 (3) | 0.0357 (5) | |
H14 | 0.4209 | 0.8700 | −0.1581 | 0.043* | |
C15 | 0.5202 (4) | 0.92742 (12) | 0.0985 (4) | 0.0464 (6) | |
H15 | 0.6546 | 0.9043 | 0.1692 | 0.056* | |
C16 | 0.5362 (4) | 0.99388 (12) | 0.0006 (4) | 0.0463 (6) | |
H16 | 0.6788 | 1.0115 | 0.0109 | 0.056* | |
C17 | 0.3634 (4) | 0.99646 (11) | −0.2073 (4) | 0.0427 (5) | |
C18 | 0.0169 (4) | 0.97291 (13) | −0.1433 (5) | 0.0508 (6) | |
H18A | −0.0374 | 0.9413 | −0.0655 | 0.076* | |
H18B | −0.0975 | 0.9869 | −0.2658 | 0.076* | |
H18C | 0.0723 | 1.0096 | −0.0532 | 0.076* | |
C19 | −0.1823 (4) | 0.76125 (14) | −0.0571 (4) | 0.0494 (6) | |
H19A | −0.2584 | 0.7236 | −0.0329 | 0.074* | |
H19B | −0.2837 | 0.7929 | −0.1358 | 0.074* | |
H19C | −0.0997 | 0.7794 | 0.0774 | 0.074* | |
C20 | 0.4718 (5) | 0.98657 (15) | 0.2017 (4) | 0.0568 (7) | |
H20A | 0.5753 | 0.9999 | 0.3353 | 0.068* | |
H20B | 0.3223 | 0.9948 | 0.1916 | 0.068* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0676 (13) | 0.0364 (9) | 0.0532 (11) | −0.0079 (9) | 0.0058 (10) | −0.0006 (8) |
O2 | 0.0630 (12) | 0.0439 (10) | 0.0448 (10) | −0.0119 (8) | 0.0151 (9) | 0.0087 (8) |
O3 | 0.0712 (12) | 0.0485 (11) | 0.0662 (12) | −0.0026 (9) | 0.0196 (10) | 0.0138 (9) |
C1 | 0.0430 (12) | 0.0359 (11) | 0.0402 (12) | −0.0042 (9) | −0.0022 (10) | 0.0013 (10) |
C2 | 0.0714 (18) | 0.0402 (13) | 0.0338 (11) | −0.0089 (11) | 0.0110 (12) | −0.0015 (10) |
C3 | 0.0641 (16) | 0.0358 (12) | 0.0516 (14) | −0.0005 (11) | 0.0227 (12) | −0.0051 (11) |
C4 | 0.0408 (12) | 0.0320 (11) | 0.0595 (14) | 0.0024 (9) | 0.0147 (10) | 0.0036 (10) |
C5 | 0.0363 (11) | 0.0321 (10) | 0.0354 (10) | −0.0007 (9) | 0.0029 (9) | 0.0057 (8) |
C6 | 0.0425 (12) | 0.0418 (12) | 0.0352 (11) | −0.0021 (10) | −0.0014 (9) | 0.0070 (9) |
C7 | 0.0425 (12) | 0.0428 (12) | 0.0319 (10) | −0.0033 (9) | −0.0046 (9) | 0.0013 (9) |
C8 | 0.0345 (10) | 0.0328 (10) | 0.0304 (10) | 0.0013 (8) | 0.0027 (8) | −0.0025 (8) |
C9 | 0.0345 (10) | 0.0292 (9) | 0.0304 (9) | 0.0031 (8) | 0.0022 (8) | −0.0003 (8) |
C10 | 0.0305 (9) | 0.0345 (10) | 0.0330 (10) | 0.0004 (8) | 0.0036 (8) | −0.0009 (8) |
C11 | 0.0498 (13) | 0.0354 (11) | 0.0365 (11) | 0.0010 (10) | −0.0054 (9) | 0.0019 (10) |
C12 | 0.0583 (14) | 0.0358 (11) | 0.0359 (11) | 0.0033 (10) | 0.0015 (10) | 0.0043 (9) |
C13 | 0.0375 (10) | 0.0289 (10) | 0.0405 (11) | 0.0031 (8) | 0.0062 (9) | 0.0000 (9) |
C14 | 0.0325 (10) | 0.0328 (10) | 0.0371 (11) | 0.0038 (8) | 0.0039 (8) | −0.0012 (9) |
C15 | 0.0387 (11) | 0.0411 (13) | 0.0497 (13) | −0.0025 (10) | −0.0006 (10) | −0.0007 (10) |
C16 | 0.0411 (12) | 0.0372 (12) | 0.0586 (14) | −0.0034 (10) | 0.0121 (11) | −0.0050 (11) |
C17 | 0.0452 (12) | 0.0324 (11) | 0.0515 (13) | 0.0037 (9) | 0.0166 (10) | −0.0030 (10) |
C18 | 0.0396 (11) | 0.0418 (13) | 0.0692 (17) | 0.0079 (10) | 0.0142 (12) | −0.0051 (12) |
C19 | 0.0402 (12) | 0.0512 (14) | 0.0595 (15) | 0.0010 (11) | 0.0196 (11) | −0.0012 (12) |
C20 | 0.0619 (16) | 0.0551 (15) | 0.0488 (14) | −0.0132 (13) | 0.0101 (12) | −0.0149 (12) |
O1—C3 | 1.451 (3) | C9—H9 | 0.9800 |
O1—H1X | 0.792 (19) | C10—C19 | 1.535 (3) |
O2—C5 | 1.442 (3) | C11—C12 | 1.550 (4) |
O2—H2X | 0.85 (5) | C11—H11A | 0.9700 |
O3—C17 | 1.214 (3) | C11—H11B | 0.9700 |
C1—C2 | 1.509 (4) | C12—C13 | 1.529 (3) |
C1—C10 | 1.537 (3) | C12—H12A | 0.9700 |
C1—H1A | 0.9700 | C12—H12B | 0.9700 |
C1—H1B | 0.9700 | C13—C17 | 1.534 (3) |
C2—C3 | 1.521 (4) | C13—C18 | 1.547 (3) |
C2—H2A | 0.9700 | C13—C14 | 1.547 (3) |
C2—H2B | 0.9700 | C14—C15 | 1.519 (3) |
C3—C4 | 1.512 (4) | C14—H14 | 0.9800 |
C3—H3 | 0.9800 | C15—C20 | 1.475 (4) |
C4—C5 | 1.540 (3) | C15—C16 | 1.530 (4) |
C4—H4A | 0.9700 | C15—H15 | 0.9800 |
C4—H4B | 0.9700 | C16—C17 | 1.483 (4) |
C5—C6 | 1.509 (3) | C16—C20 | 1.515 (4) |
C5—C10 | 1.562 (3) | C16—H16 | 0.9800 |
C6—C7 | 1.327 (4) | C18—H18A | 0.9599 |
C6—H6 | 0.9300 | C18—H18B | 0.9599 |
C7—C8 | 1.504 (3) | C18—H18C | 0.9599 |
C7—H7 | 0.9300 | C19—H19A | 0.9599 |
C8—C14 | 1.517 (3) | C19—H19B | 0.9599 |
C8—C9 | 1.551 (3) | C19—H19C | 0.9599 |
C8—H8 | 0.9800 | C20—H20A | 0.9700 |
C9—C11 | 1.541 (3) | C20—H20B | 0.9700 |
C9—C10 | 1.553 (3) | ||
C3—O1—H1X | 112 (3) | C9—C11—H11A | 108.9 |
C5—O2—H2X | 107 (4) | C12—C11—H11A | 108.9 |
C2—C1—C10 | 115.01 (19) | C9—C11—H11B | 108.9 |
C2—C1—H1A | 108.5 | C12—C11—H11B | 108.9 |
C10—C1—H1A | 108.5 | H11A—C11—H11B | 107.7 |
C2—C1—H1B | 108.5 | C13—C12—C11 | 109.74 (19) |
C10—C1—H1B | 108.5 | C13—C12—H12A | 109.7 |
H1A—C1—H1B | 107.5 | C11—C12—H12A | 109.7 |
C1—C2—C3 | 111.4 (2) | C13—C12—H12B | 109.7 |
C1—C2—H2A | 109.4 | C11—C12—H12B | 109.7 |
C3—C2—H2A | 109.4 | H12A—C12—H12B | 108.2 |
C1—C2—H2B | 109.4 | C12—C13—C17 | 117.64 (19) |
C3—C2—H2B | 109.4 | C12—C13—C18 | 107.9 (2) |
H2A—C2—H2B | 108.0 | C17—C13—C18 | 106.49 (18) |
O1—C3—C4 | 107.5 (2) | C12—C13—C14 | 106.79 (17) |
O1—C3—C2 | 111.8 (2) | C17—C13—C14 | 100.70 (17) |
C4—C3—C2 | 110.5 (2) | C18—C13—C14 | 117.7 (2) |
O1—C3—H3 | 109.0 | C8—C14—C15 | 123.38 (18) |
C4—C3—H3 | 109.0 | C8—C14—C13 | 111.09 (17) |
C2—C3—H3 | 109.0 | C15—C14—C13 | 107.45 (18) |
C3—C4—C5 | 113.6 (2) | C8—C14—H14 | 104.4 |
C3—C4—H4A | 108.8 | C15—C14—H14 | 104.4 |
C5—C4—H4A | 108.8 | C13—C14—H14 | 104.4 |
C3—C4—H4B | 108.8 | C20—C15—C14 | 121.4 (2) |
C5—C4—H4B | 108.8 | C20—C15—C16 | 60.51 (18) |
H4A—C4—H4B | 107.7 | C14—C15—C16 | 105.6 (2) |
O2—C5—C6 | 106.38 (17) | C20—C15—H15 | 117.9 |
O2—C5—C4 | 107.91 (19) | C14—C15—H15 | 117.9 |
C6—C5—C4 | 108.69 (19) | C16—C15—H15 | 117.9 |
O2—C5—C10 | 110.33 (17) | C17—C16—C20 | 118.4 (2) |
C6—C5—C10 | 110.90 (18) | C17—C16—C15 | 106.9 (2) |
C4—C5—C10 | 112.40 (18) | C20—C16—C15 | 57.95 (18) |
C7—C6—C5 | 124.6 (2) | C17—C16—H16 | 119.1 |
C7—C6—H6 | 117.7 | C20—C16—H16 | 119.1 |
C5—C6—H6 | 117.7 | C15—C16—H16 | 119.1 |
C6—C7—C8 | 123.3 (2) | O3—C17—C16 | 125.1 (2) |
C6—C7—H7 | 118.4 | O3—C17—C13 | 125.4 (2) |
C8—C7—H7 | 118.4 | C16—C17—C13 | 109.4 (2) |
C7—C8—C14 | 114.79 (17) | C13—C18—H18A | 109.5 |
C7—C8—C9 | 110.28 (17) | C13—C18—H18B | 109.5 |
C14—C8—C9 | 106.88 (17) | H18A—C18—H18B | 109.5 |
C7—C8—H8 | 108.2 | C13—C18—H18C | 109.5 |
C14—C8—H8 | 108.2 | H18A—C18—H18C | 109.5 |
C9—C8—H8 | 108.2 | H18B—C18—H18C | 109.5 |
C11—C9—C8 | 112.27 (17) | C10—C19—H19A | 109.5 |
C11—C9—C10 | 115.91 (17) | C10—C19—H19B | 109.5 |
C8—C9—C10 | 110.41 (16) | H19A—C19—H19B | 109.5 |
C11—C9—H9 | 105.8 | C10—C19—H19C | 109.5 |
C8—C9—H9 | 105.8 | H19A—C19—H19C | 109.5 |
C10—C9—H9 | 105.8 | H19B—C19—H19C | 109.5 |
C19—C10—C1 | 106.99 (18) | C15—C20—C16 | 61.54 (18) |
C19—C10—C9 | 110.70 (19) | C15—C20—H20A | 117.6 |
C1—C10—C9 | 113.86 (17) | C16—C20—H20A | 117.6 |
C19—C10—C5 | 110.21 (19) | C15—C20—H20B | 117.6 |
C1—C10—C5 | 108.32 (17) | C16—C20—H20B | 117.6 |
C9—C10—C5 | 106.75 (16) | H20A—C20—H20B | 114.7 |
C9—C11—C12 | 113.41 (19) | ||
C10—C1—C2—C3 | 56.5 (3) | C8—C9—C11—C12 | 50.3 (3) |
C1—C2—C3—O1 | 65.3 (3) | C10—C9—C11—C12 | 178.5 (2) |
C1—C2—C3—C4 | −54.4 (3) | C9—C11—C12—C13 | −52.8 (3) |
O1—C3—C4—C5 | −68.1 (3) | C11—C12—C13—C17 | 171.19 (19) |
C2—C3—C4—C5 | 54.2 (3) | C11—C12—C13—C18 | −68.4 (2) |
C3—C4—C5—O2 | 68.5 (2) | C11—C12—C13—C14 | 59.1 (2) |
C3—C4—C5—C6 | −176.49 (19) | C7—C8—C14—C15 | −43.6 (3) |
C3—C4—C5—C10 | −53.4 (3) | C9—C8—C14—C15 | −166.2 (2) |
O2—C5—C6—C7 | −139.6 (3) | C7—C8—C14—C13 | −173.34 (18) |
C4—C5—C6—C7 | 104.5 (3) | C9—C8—C14—C13 | 64.0 (2) |
C10—C5—C6—C7 | −19.6 (4) | C12—C13—C14—C8 | −67.9 (2) |
C5—C6—C7—C8 | 3.0 (4) | C17—C13—C14—C8 | 168.77 (17) |
C6—C7—C8—C14 | −138.5 (3) | C18—C13—C14—C8 | 53.6 (2) |
C6—C7—C8—C9 | −17.7 (3) | C12—C13—C14—C15 | 154.5 (2) |
C7—C8—C9—C11 | −179.5 (2) | C17—C13—C14—C15 | 31.1 (2) |
C14—C8—C9—C11 | −54.1 (2) | C18—C13—C14—C15 | −84.1 (2) |
C7—C8—C9—C10 | 49.5 (2) | C8—C14—C15—C20 | −89.3 (3) |
C14—C8—C9—C10 | 174.90 (16) | C13—C14—C15—C20 | 41.9 (3) |
C2—C1—C10—C19 | −171.9 (2) | C8—C14—C15—C16 | −154.0 (2) |
C2—C1—C10—C9 | 65.5 (3) | C13—C14—C15—C16 | −22.7 (3) |
C2—C1—C10—C5 | −53.1 (3) | C20—C15—C16—C17 | −113.3 (2) |
C11—C9—C10—C19 | −75.2 (2) | C14—C15—C16—C17 | 4.3 (3) |
C8—C9—C10—C19 | 53.9 (2) | C14—C15—C16—C20 | 117.7 (2) |
C11—C9—C10—C1 | 45.4 (2) | C20—C16—C17—O3 | 135.8 (3) |
C8—C9—C10—C1 | 174.43 (17) | C15—C16—C17—O3 | −161.9 (2) |
C11—C9—C10—C5 | 164.84 (18) | C20—C16—C17—C13 | −46.3 (3) |
C8—C9—C10—C5 | −66.1 (2) | C15—C16—C17—C13 | 15.9 (3) |
O2—C5—C10—C19 | 46.3 (2) | C12—C13—C17—O3 | 33.6 (3) |
C6—C5—C10—C19 | −71.3 (2) | C18—C13—C17—O3 | −87.6 (3) |
C4—C5—C10—C19 | 166.8 (2) | C14—C13—C17—O3 | 149.1 (2) |
O2—C5—C10—C1 | −70.4 (2) | C12—C13—C17—C16 | −144.3 (2) |
C6—C5—C10—C1 | 172.00 (19) | C18—C13—C17—C16 | 94.6 (2) |
C4—C5—C10—C1 | 50.1 (2) | C14—C13—C17—C16 | −28.8 (2) |
O2—C5—C10—C9 | 166.61 (17) | C14—C15—C20—C16 | −90.9 (3) |
C6—C5—C10—C9 | 49.0 (2) | C17—C16—C20—C15 | 93.0 (2) |
C4—C5—C10—C9 | −72.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2X···O1 | 0.85 (5) | 1.98 (4) | 2.734 (3) | 148 (6) |
O1—H1X···O3i | 0.79 (2) | 2.02 (2) | 2.811 (3) | 178 (4) |
Symmetry code: (i) −x, y−1/2, −z−1. |
Experimental details
Crystal data | |
Chemical formula | C20H28O3 |
Mr | 316.42 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 296 |
a, b, c (Å) | 6.5158 (9), 20.592 (3), 6.5877 (9) |
β (°) | 107.837 (2) |
V (Å3) | 841.4 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.976, 0.984 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5279, 1884, 1739 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.110, 1.06 |
No. of reflections | 1884 |
No. of parameters | 216 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.17 |
Computer programs: APEX2 (Bruker, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2X···O1 | 0.85 (5) | 1.98 (4) | 2.734 (3) | 148 (6) |
O1—H1X···O3i | 0.792 (19) | 2.019 (19) | 2.811 (3) | 178 (4) |
Symmetry code: (i) −x, y−1/2, −z−1. |
Drospirenone is a new contraceptive drug with the special antimineralocorticoid and antiandrogenic properties (Muhn et al., 1995). In our attempts to synthesize drospirenone, the title compound, (I), was obtained as an intermediate by the alcoholysis of, 3β-acetoxy-5-hydroxy-15β,16β-methylene-5β-androst-6-en-17-one. Here we report the crystal structure of (I).
In the cyclopropyl ring C15/C16/C20, the bond lengths C16—C20 and C15—C20 are different [1.515 (4) versus 1.475 (4) Å], which is also found in 3β-acetoxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one [1.511 (5) and 1.473 (4) Å; Zhou et al., 2007]. The difference in these bond lengths might be caused by a hyperconjugation interaction between the C=O π-bonding and C16—C20 σ-bonding orbitals. However, in the analogous structure of 3β-acetoxy-17,17-ethylenedioxy-15β,16β-methylene-5-androsten-7β-ol these bond lenghts are almost equal [1.499 (6) and 1.493 (6) Å; Zhou et al., 2006].
In the steroid skeleton, ring A has a regular chair conformation, while ring C has a slightly distorted chair conformation. Ring B shows a asymmetric half-chair conformation and ring D is in an envelope conformation. In ring B, atom C9 and atom C10 deviate by 0.390 (4) and -0.435 (4) Å from the mean plane calculated through the ring C5—C8, respectively. In ring D, C13 deviates by 0.486 (3) Å from the mean plane of C14—C17, which makes a dihedral angle of 64.5 (1)° with the cyclopropyl ring C15/C16/C20. In the crystal structure, an intermolecular O—H···O hydrogen bond is found (Table 1), which links the molecules into ribbons along the b axis (Fig. 2). In addition, an intramolecular O—H···O hydrogen bond is found (Table 1).