organic compounds
17α-Ethynyl-3-methoxyestra-1,3,5(10),9(11)-tetraen-17-ol
aCollege of Chemistry and Chemical Engineering, Donghua University, Shanghai 201620, People's Republic of China, and bCollege of Environmental Science and Engineering, Donghua University, Shanghai 201620, People's Republic of China
*Correspondence e-mail: hongqili@dhu.edu.cn
In the title compound, C21H24O2, rings B, C and D adopt half-chair, distorted half-chair and envelope conformations, respectively. In the there is an intermolecular O—H⋯O hydrogen bond. The molecules are arranged in a head-to-tail fashion, with the methoxy and hydroxy groups forming a two-dimensional hydrogen-bond network.
Related literature
For related literature, see: Doussot et al. (1995); Ekhato et al. (2002); Sedee et al. (1985); Steiner et al. (1997).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808005254/wn2237sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808005254/wn2237Isup2.hkl
The title compound was prepared, in 90% yield, by methylation of 3,17β-dihydroxy-19-norpregna-1,3,5(10),9(11)-tetraen-20-yne (Ekhato et al., 2002) with methyl iodide and potassium carbonate at room temperature. Crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution in ethyl acetate and petroleum ether (1:1, v/v).
The H atom bonded to O was located in a difference map and refined with a distance restraint of O—H = 0.82 (4) Å. Other H atoms were positioned geometrically and refined using a riding model, with C—H = 0.93 Å for benzene and acetylenic C—H, 0.96 Å for methyl C—H, 0.97 Å for methylene C—H, and 0.98Å for methine C—H; Uiso(H) = 1.2Ueq(C) except for methyl groups, where Uiso(H) = 1.5Ueq(C). In the absence of significant
effects, Friedel pairs were merged.Data collection: SMART (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).C21H24O2 | Dx = 1.216 Mg m−3 |
Mr = 308.40 | Melting point: 145 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.3773 (6) Å | Cell parameters from 3971 reflections |
b = 10.7430 (9) Å | θ = 5.4–53.4° |
c = 21.2555 (18) Å | µ = 0.08 mm−1 |
V = 1684.6 (2) Å3 | T = 293 K |
Z = 4 | Prismatic, colorless |
F(000) = 664 | 0.50 × 0.43 × 0.35 mm |
Rigaku FCR CCD area-detector diffractometer | 2127 independent reflections |
Radiation source: fine-focus sealed tube | 1884 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
ϕ and ω scans | θmax = 27.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | h = −7→9 |
Tmin = 0.824, Tmax = 1.000 | k = −13→9 |
9960 measured reflections | l = −25→27 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0757P)2 + 0.0067P] where P = (Fo2 + 2Fc2)/3 |
2127 reflections | (Δ/σ)max = 0.001 |
214 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C21H24O2 | V = 1684.6 (2) Å3 |
Mr = 308.40 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.3773 (6) Å | µ = 0.08 mm−1 |
b = 10.7430 (9) Å | T = 293 K |
c = 21.2555 (18) Å | 0.50 × 0.43 × 0.35 mm |
Rigaku FCR CCD area-detector diffractometer | 2127 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2004) | 1884 reflections with I > 2σ(I) |
Tmin = 0.824, Tmax = 1.000 | Rint = 0.071 |
9960 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.114 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.20 e Å−3 |
2127 reflections | Δρmin = −0.24 e Å−3 |
214 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 | 0.3222 (3) | 0.77612 (18) | 0.73106 (7) | 0.0684 (5) | |
O2 | 0.5307 (3) | 0.26039 (16) | 1.17027 (8) | 0.0583 (5) | |
C1 | 0.2555 (3) | 0.6031 (2) | 0.87459 (10) | 0.0502 (5) | |
H1 | 0.1618 | 0.5584 | 0.8932 | 0.060* | |
C2 | 0.2245 (3) | 0.6607 (2) | 0.81810 (10) | 0.0556 (6) | |
H2 | 0.1108 | 0.6561 | 0.7994 | 0.067* | |
C3 | 0.3626 (3) | 0.7256 (2) | 0.78916 (10) | 0.0497 (5) | |
C4 | 0.5296 (3) | 0.7326 (2) | 0.81737 (10) | 0.0503 (5) | |
H4 | 0.6227 | 0.7762 | 0.7978 | 0.060* | |
C5 | 0.5612 (3) | 0.67502 (19) | 0.87522 (10) | 0.0422 (5) | |
C6 | 0.7485 (3) | 0.6809 (2) | 0.90286 (11) | 0.0548 (6) | |
H6A | 0.7993 | 0.7628 | 0.8951 | 0.066* | |
H6B | 0.8250 | 0.6203 | 0.8820 | 0.066* | |
C7 | 0.7495 (3) | 0.6558 (2) | 0.97282 (11) | 0.0496 (5) | |
H7A | 0.6936 | 0.7251 | 0.9947 | 0.059* | |
H7B | 0.8737 | 0.6487 | 0.9873 | 0.059* | |
C8 | 0.6478 (2) | 0.53696 (19) | 0.98837 (9) | 0.0362 (4) | |
H8 | 0.7043 | 0.4684 | 0.9652 | 0.043* | |
C9 | 0.4518 (3) | 0.54791 (17) | 0.96698 (9) | 0.0345 (4) | |
C10 | 0.4221 (3) | 0.60908 (18) | 0.90521 (9) | 0.0380 (4) | |
C11 | 0.3154 (3) | 0.50772 (19) | 1.00285 (9) | 0.0376 (4) | |
H11 | 0.1985 | 0.5207 | 0.9878 | 0.045* | |
C12 | 0.3331 (3) | 0.44369 (19) | 1.06504 (9) | 0.0379 (4) | |
H12A | 0.2522 | 0.3726 | 1.0663 | 0.045* | |
H12B | 0.2980 | 0.5004 | 1.0984 | 0.045* | |
C13 | 0.5267 (3) | 0.40034 (17) | 1.07587 (8) | 0.0358 (4) | |
C14 | 0.6545 (3) | 0.50617 (18) | 1.05775 (9) | 0.0369 (4) | |
H14 | 0.6133 | 0.5804 | 1.0804 | 0.044* | |
C15 | 0.8389 (3) | 0.4696 (2) | 1.08594 (10) | 0.0517 (6) | |
H15A | 0.9140 | 0.4288 | 1.0547 | 0.062* | |
H15B | 0.9023 | 0.5424 | 1.1015 | 0.062* | |
C16 | 0.7939 (3) | 0.3803 (3) | 1.13995 (11) | 0.0572 (6) | |
H16A | 0.8467 | 0.4097 | 1.1790 | 0.069* | |
H16B | 0.8408 | 0.2978 | 1.1311 | 0.069* | |
C17 | 0.5855 (3) | 0.3774 (2) | 1.14476 (10) | 0.0447 (5) | |
C18 | 0.5615 (3) | 0.28188 (19) | 1.03758 (9) | 0.0471 (5) | |
H18A | 0.5295 | 0.2962 | 0.9944 | 0.071* | |
H18B | 0.4893 | 0.2151 | 1.0541 | 0.071* | |
H18C | 0.6874 | 0.2601 | 1.0402 | 0.071* | |
C20 | 0.4291 (5) | 0.8770 (3) | 0.70975 (14) | 0.0782 (9) | |
H19A | 0.5512 | 0.8493 | 0.7030 | 0.117* | |
H19B | 0.4284 | 0.9419 | 0.7408 | 0.117* | |
H19C | 0.3801 | 0.9083 | 0.6710 | 0.117* | |
C21 | 0.5210 (3) | 0.4781 (2) | 1.18698 (9) | 0.0500 (5) | |
C22 | 0.4707 (4) | 0.5547 (3) | 1.22112 (11) | 0.0644 (7) | |
H21 | 0.4303 | 0.6162 | 1.2485 | 0.077* | |
H3 | 0.425 (5) | 0.260 (3) | 1.1812 (13) | 0.079 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0730 (12) | 0.0800 (12) | 0.0523 (9) | 0.0059 (10) | 0.0010 (9) | 0.0254 (8) |
O2 | 0.0669 (13) | 0.0551 (10) | 0.0528 (9) | 0.0104 (9) | 0.0036 (8) | 0.0111 (7) |
C1 | 0.0378 (11) | 0.0683 (14) | 0.0445 (11) | −0.0046 (11) | 0.0001 (9) | 0.0071 (10) |
C2 | 0.0426 (12) | 0.0772 (16) | 0.0472 (12) | 0.0009 (12) | −0.0074 (9) | 0.0103 (12) |
C3 | 0.0527 (12) | 0.0535 (12) | 0.0429 (11) | 0.0087 (11) | 0.0024 (9) | 0.0062 (10) |
C4 | 0.0492 (13) | 0.0485 (12) | 0.0532 (12) | −0.0034 (10) | 0.0119 (10) | 0.0080 (10) |
C5 | 0.0393 (11) | 0.0396 (10) | 0.0477 (11) | −0.0016 (8) | 0.0050 (9) | −0.0006 (9) |
C6 | 0.0379 (11) | 0.0630 (14) | 0.0634 (14) | −0.0149 (11) | 0.0014 (10) | 0.0112 (12) |
C7 | 0.0365 (10) | 0.0542 (12) | 0.0580 (13) | −0.0110 (10) | −0.0068 (9) | 0.0003 (10) |
C8 | 0.0274 (8) | 0.0414 (10) | 0.0396 (10) | −0.0003 (8) | 0.0002 (7) | −0.0059 (8) |
C9 | 0.0311 (9) | 0.0332 (9) | 0.0392 (9) | −0.0010 (8) | −0.0021 (7) | −0.0051 (7) |
C10 | 0.0350 (10) | 0.0392 (10) | 0.0399 (9) | 0.0004 (8) | 0.0028 (8) | −0.0037 (8) |
C11 | 0.0276 (8) | 0.0424 (10) | 0.0429 (10) | 0.0019 (8) | −0.0013 (8) | −0.0005 (8) |
C12 | 0.0321 (10) | 0.0410 (10) | 0.0406 (10) | −0.0013 (8) | 0.0003 (8) | −0.0013 (8) |
C13 | 0.0342 (9) | 0.0373 (9) | 0.0358 (9) | 0.0037 (8) | −0.0004 (7) | −0.0044 (7) |
C14 | 0.0301 (9) | 0.0410 (10) | 0.0397 (9) | 0.0024 (8) | −0.0031 (7) | −0.0086 (8) |
C15 | 0.0348 (11) | 0.0690 (15) | 0.0515 (12) | 0.0035 (11) | −0.0083 (9) | −0.0047 (11) |
C16 | 0.0463 (12) | 0.0728 (16) | 0.0525 (13) | 0.0130 (12) | −0.0124 (10) | 0.0021 (11) |
C17 | 0.0474 (11) | 0.0477 (11) | 0.0390 (10) | 0.0075 (10) | −0.0031 (8) | 0.0003 (9) |
C18 | 0.0522 (12) | 0.0395 (10) | 0.0496 (11) | 0.0024 (10) | 0.0042 (10) | −0.0091 (9) |
C20 | 0.101 (2) | 0.0648 (16) | 0.0685 (16) | 0.0106 (18) | 0.0222 (16) | 0.0199 (13) |
C21 | 0.0557 (13) | 0.0572 (13) | 0.0369 (10) | −0.0028 (11) | −0.0062 (9) | −0.0045 (10) |
C22 | 0.0740 (17) | 0.0709 (16) | 0.0482 (12) | 0.0020 (15) | −0.0018 (12) | −0.0185 (12) |
O1—C3 | 1.381 (3) | C11—C12 | 1.496 (3) |
O1—C20 | 1.415 (4) | C11—H11 | 0.9300 |
O2—C17 | 1.428 (3) | C12—C13 | 1.520 (3) |
O2—H3 | 0.82 (4) | C12—H12A | 0.9700 |
C1—C2 | 1.370 (3) | C12—H12B | 0.9700 |
C1—C10 | 1.392 (3) | C13—C14 | 1.526 (3) |
C1—H1 | 0.9300 | C13—C18 | 1.532 (3) |
C2—C3 | 1.379 (3) | C13—C17 | 1.547 (3) |
C2—H2 | 0.9300 | C14—C15 | 1.538 (3) |
C3—C4 | 1.373 (3) | C14—H14 | 0.9800 |
C4—C5 | 1.396 (3) | C15—C16 | 1.532 (3) |
C4—H4 | 0.9300 | C15—H15A | 0.9700 |
C5—C10 | 1.400 (3) | C15—H15B | 0.9700 |
C5—C6 | 1.503 (3) | C16—C17 | 1.542 (3) |
C6—C7 | 1.511 (3) | C16—H16A | 0.9700 |
C6—H6A | 0.9700 | C16—H16B | 0.9700 |
C6—H6B | 0.9700 | C17—C21 | 1.483 (3) |
C7—C8 | 1.517 (3) | C18—H18A | 0.9600 |
C7—H7A | 0.9700 | C18—H18B | 0.9600 |
C7—H7B | 0.9700 | C18—H18C | 0.9600 |
C8—C14 | 1.512 (3) | C20—H19A | 0.9600 |
C8—C9 | 1.520 (2) | C20—H19B | 0.9600 |
C8—H8 | 0.9800 | C20—H19C | 0.9600 |
C9—C11 | 1.334 (3) | C21—C22 | 1.159 (3) |
C9—C10 | 1.484 (3) | C22—H21 | 0.9300 |
C3—O1—C20 | 117.8 (2) | C11—C12—H12B | 109.5 |
C17—O2—H3 | 113 (2) | C13—C12—H12B | 109.5 |
C2—C1—C10 | 122.4 (2) | H12A—C12—H12B | 108.0 |
C2—C1—H1 | 118.8 | C12—C13—C14 | 108.29 (15) |
C10—C1—H1 | 118.8 | C12—C13—C18 | 109.35 (17) |
C1—C2—C3 | 119.7 (2) | C14—C13—C18 | 112.42 (16) |
C1—C2—H2 | 120.1 | C12—C13—C17 | 117.09 (16) |
C3—C2—H2 | 120.1 | C14—C13—C17 | 100.62 (15) |
C4—C3—C2 | 119.7 (2) | C18—C13—C17 | 108.90 (16) |
C4—C3—O1 | 124.2 (2) | C8—C14—C13 | 112.88 (15) |
C2—C3—O1 | 116.0 (2) | C8—C14—C15 | 117.70 (17) |
C3—C4—C5 | 120.7 (2) | C13—C14—C15 | 104.93 (16) |
C3—C4—H4 | 119.7 | C8—C14—H14 | 106.9 |
C5—C4—H4 | 119.7 | C13—C14—H14 | 106.9 |
C4—C5—C10 | 120.2 (2) | C15—C14—H14 | 106.9 |
C4—C5—C6 | 118.6 (2) | C16—C15—C14 | 105.10 (17) |
C10—C5—C6 | 121.13 (19) | C16—C15—H15A | 110.7 |
C5—C6—C7 | 112.43 (18) | C14—C15—H15A | 110.7 |
C5—C6—H6A | 109.1 | C16—C15—H15B | 110.7 |
C7—C6—H6A | 109.1 | C14—C15—H15B | 110.7 |
C5—C6—H6B | 109.1 | H15A—C15—H15B | 108.8 |
C7—C6—H6B | 109.1 | C15—C16—C17 | 106.14 (18) |
H6A—C6—H6B | 107.9 | C15—C16—H16A | 110.5 |
C6—C7—C8 | 111.26 (18) | C17—C16—H16A | 110.5 |
C6—C7—H7A | 109.4 | C15—C16—H16B | 110.5 |
C8—C7—H7A | 109.4 | C17—C16—H16B | 110.5 |
C6—C7—H7B | 109.4 | H16A—C16—H16B | 108.7 |
C8—C7—H7B | 109.4 | O2—C17—C21 | 108.75 (17) |
H7A—C7—H7B | 108.0 | O2—C17—C16 | 109.0 (2) |
C14—C8—C7 | 112.36 (16) | C21—C17—C16 | 110.2 (2) |
C14—C8—C9 | 109.86 (15) | O2—C17—C13 | 114.86 (18) |
C7—C8—C9 | 109.89 (17) | C21—C17—C13 | 111.54 (17) |
C14—C8—H8 | 108.2 | C16—C17—C13 | 102.34 (18) |
C7—C8—H8 | 108.2 | C13—C18—H18A | 109.5 |
C9—C8—H8 | 108.2 | C13—C18—H18B | 109.5 |
C11—C9—C10 | 122.52 (17) | H18A—C18—H18B | 109.5 |
C11—C9—C8 | 121.42 (17) | C13—C18—H18C | 109.5 |
C10—C9—C8 | 116.03 (16) | H18A—C18—H18C | 109.5 |
C1—C10—C5 | 117.21 (18) | H18B—C18—H18C | 109.5 |
C1—C10—C9 | 121.55 (18) | O1—C20—H19A | 109.5 |
C5—C10—C9 | 121.24 (17) | O1—C20—H19B | 109.5 |
C9—C11—C12 | 126.00 (18) | H19A—C20—H19B | 109.5 |
C9—C11—H11 | 117.0 | O1—C20—H19C | 109.5 |
C12—C11—H11 | 117.0 | H19A—C20—H19C | 109.5 |
C11—C12—C13 | 110.91 (15) | H19B—C20—H19C | 109.5 |
C11—C12—H12A | 109.5 | C22—C21—C17 | 178.4 (2) |
C13—C12—H12A | 109.5 | C21—C22—H21 | 180.0 |
C10—C1—C2—C3 | 1.2 (4) | C11—C12—C13—C14 | 45.3 (2) |
C1—C2—C3—C4 | −0.4 (4) | C11—C12—C13—C18 | −77.5 (2) |
C1—C2—C3—O1 | 177.2 (2) | C11—C12—C13—C17 | 158.11 (17) |
C20—O1—C3—C4 | −24.5 (3) | C7—C8—C14—C13 | 170.07 (16) |
C20—O1—C3—C2 | 158.0 (2) | C9—C8—C14—C13 | 47.4 (2) |
C2—C3—C4—C5 | −0.2 (4) | C7—C8—C14—C15 | −67.4 (2) |
O1—C3—C4—C5 | −177.6 (2) | C9—C8—C14—C15 | 169.92 (17) |
C3—C4—C5—C10 | 0.0 (3) | C12—C13—C14—C8 | −65.2 (2) |
C3—C4—C5—C6 | 177.5 (2) | C18—C13—C14—C8 | 55.8 (2) |
C4—C5—C6—C7 | 160.3 (2) | C17—C13—C14—C8 | 171.47 (15) |
C10—C5—C6—C7 | −22.3 (3) | C12—C13—C14—C15 | 165.44 (16) |
C5—C6—C7—C8 | 50.9 (3) | C18—C13—C14—C15 | −73.6 (2) |
C6—C7—C8—C14 | 177.20 (18) | C17—C13—C14—C15 | 42.07 (18) |
C6—C7—C8—C9 | −60.2 (2) | C8—C14—C15—C16 | −149.88 (18) |
C14—C8—C9—C11 | −13.5 (3) | C13—C14—C15—C16 | −23.4 (2) |
C7—C8—C9—C11 | −137.59 (19) | C14—C15—C16—C17 | −4.8 (2) |
C14—C8—C9—C10 | 164.70 (15) | C15—C16—C17—O2 | 152.64 (18) |
C7—C8—C9—C10 | 40.6 (2) | C15—C16—C17—C21 | −88.1 (2) |
C2—C1—C10—C5 | −1.3 (3) | C15—C16—C17—C13 | 30.6 (2) |
C2—C1—C10—C9 | 178.8 (2) | C12—C13—C17—O2 | 80.7 (2) |
C4—C5—C10—C1 | 0.7 (3) | C14—C13—C17—O2 | −162.21 (17) |
C6—C5—C10—C1 | −176.7 (2) | C18—C13—C17—O2 | −43.9 (2) |
C4—C5—C10—C9 | −179.47 (17) | C12—C13—C17—C21 | −43.6 (3) |
C6—C5—C10—C9 | 3.1 (3) | C14—C13—C17—C21 | 73.5 (2) |
C11—C9—C10—C1 | −14.8 (3) | C18—C13—C17—C21 | −168.21 (19) |
C8—C9—C10—C1 | 167.05 (19) | C12—C13—C17—C16 | −161.36 (18) |
C11—C9—C10—C5 | 165.4 (2) | C14—C13—C17—C16 | −44.3 (2) |
C8—C9—C10—C5 | −12.8 (3) | C18—C13—C17—C16 | 74.0 (2) |
C10—C9—C11—C12 | 179.06 (17) | O2—C17—C21—C22 | 25 (10) |
C8—C9—C11—C12 | −2.9 (3) | C16—C17—C21—C22 | −95 (10) |
C9—C11—C12—C13 | −14.1 (3) | C13—C17—C21—C22 | 152 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H3···O1i | 0.82 (4) | 2.14 (4) | 2.933 (3) | 163 (3) |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C21H24O2 |
Mr | 308.40 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 7.3773 (6), 10.7430 (9), 21.2555 (18) |
V (Å3) | 1684.6 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.50 × 0.43 × 0.35 |
Data collection | |
Diffractometer | Rigaku FCR CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2004) |
Tmin, Tmax | 0.824, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9960, 2127, 1884 |
Rint | 0.071 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.114, 1.03 |
No. of reflections | 2127 |
No. of parameters | 214 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.24 |
Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H3···O1i | 0.82 (4) | 2.14 (4) | 2.933 (3) | 163 (3) |
Symmetry code: (i) −x+1/2, −y+1, z+1/2. |
Acknowledgements
Financial support of the project by the Program for Changjiang Scholars and Innovative Research Team in the University (No. IRT0526) and Shanghai Natural Science Foundation (No. 06ZR14001) is acknowledged.
References
Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Doussot, J., Garreau, R., Dallery, L., Guette, J.-P. & Guy, A. (1995). Bull. Soc. Chim. Fr. 132, 59–66. CAS Google Scholar
Ekhato, I. V., Hurley, T., Lovdahl, M., Revitte, T. J., Guo, L., Huang, Y., Clipper, S. & Colson, C. (2002). Steroids, 67, 165–174. Web of Science CrossRef PubMed CAS Google Scholar
Sedee, A. G. J., van Henegouwen, G. M. J. B., de Vries, M. E. & Erkelens, C. (1985). Steroids, 45, 101–118. CrossRef CAS PubMed Web of Science Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Steiner, T., Lutz, B., van der Maas, J., Veldman, N., Schreurs, A. M. M., Kroon, J. & Kanters, J. A. (1997). Chem. Commun. pp. 191–192. CSD CrossRef Web of Science Google Scholar
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The title compound is a photodecomposition product of mestranol (Sedee et al., 1985) and can be used as an intermediate for the synthesis of steroidal drugs. The preparation of the title compound starting from mestranol, through an oxidative dehydrogenation with 2,3-dichloro-5,6-dicyanoquinone (DDQ) in methanol, was reported by Doussot et al. (1995) However, no crystal structure of the title compound has been reported thus far. Here we present the crystal structure of 17α-ethinyl-3-methoxyestra-1,3,5(10),9(11)-tetraen-17-ol.
The geometry (Fig. 1) of the steroid skeleton does not differ significantly from that of mestranol (Steiner et al., 1997), except, of course, for the C?C bond in ring C. There is an intermolecular hydrogen bond O2—H3···O1, but no intra- or intermolecular hydrogen bonding between hydroxy and ethynyl groups is observed. The molecules are arranged in a head-to-tail fashion, different from the head-to-head fashion observed in mestranol, with the methoxy and hydroxy groups forming a two-dimensional hydrogen bond network (Fig. 2).