Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807056000/nc2066sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807056000/nc2066Isup2.hkl |
CCDC reference: 672899
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.059
- wR factor = 0.150
- Data-to-parameter ratio = 10.2
checkCIF/PLATON results
No syntax errors found
Alert level C STRVA01_ALERT_4_C Flack parameter is too small From the CIF: _refine_ls_abs_structure_Flack -10.000 From the CIF: _refine_ls_abs_structure_Flack_su 10.000 PLAT032_ALERT_4_C Std. Uncertainty in Flack Parameter too High ... 10.00 PLAT033_ALERT_2_C Flack Parameter Value Deviates 2 * su from zero. -10.00 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.54 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.16 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C21
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 27.00 From the CIF: _reflns_number_total 2437 Count of symmetry unique reflns 2444 Completeness (_total/calc) 99.71% 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 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 C5 = . R 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 = . R 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 6 ALERT level C = Check and explain 12 ALERT level G = General alerts; check 11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Muhn et al. (1995) and Zhou et al. (2006, 2007); Bittler et al. (1984).
The title compound was synthesized according to literature methods (Bittler et al., 1984). Crystals suitable for X-ray diffraction analysis were obtained by slow evaporation of the solvent from a solution of the title compound in isopropyl ether.
Because no strong anomalous scattering atoms are present, the absolute structure cannot be determined. Therefore Friedel pairs were merged in the refinement. The absolute stereochemistry of the compound (I) is known from the synthetic route. The C—H H atoms were placed in calculated positions and were refined using a riding model with Uiso(H) = 1.2 Ueq(C) [or 1.5Ueq(methyl C)] and C—H distances of 0.93–0.98 Å. The hydroxy H atom was positioned with idealized geometry allowed to rotate but not to tip and was refined using a riding model, with O—H = 0.82Å and Uiso(H) = 1.5 Ueq(O).
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.05; Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. Crystal structure of (I) with labelling and displacement ellipsoids drawn at the 30% probability level. |
C22H30O4 | F(000) = 776 |
Mr = 358.46 | Dx = 1.221 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 833 reflections |
a = 7.160 (4) Å | θ = 2.8–26.8° |
b = 14.541 (8) Å | µ = 0.08 mm−1 |
c = 18.733 (10) Å | T = 293 K |
V = 1950.4 (18) Å3 | Block, colorless |
Z = 4 | 0.40 × 0.35 × 0.25 mm |
Bruker SMART CCD area-detector diffractometer | 2437 independent reflections |
Radiation source: fine-focus sealed tube | 2036 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
phi and ω scans | θmax = 27.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −9→6 |
Tmin = 0.957, Tmax = 0.971 | k = −18→13 |
9446 measured reflections | l = −23→23 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0893P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.17 | (Δ/σ)max < 0.001 |
2437 reflections | Δρmax = 0.37 e Å−3 |
239 parameters | Δρmin = −0.26 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.032 (4) |
C22H30O4 | V = 1950.4 (18) Å3 |
Mr = 358.46 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.160 (4) Å | µ = 0.08 mm−1 |
b = 14.541 (8) Å | T = 293 K |
c = 18.733 (10) Å | 0.40 × 0.35 × 0.25 mm |
Bruker SMART CCD area-detector diffractometer | 2437 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | 2036 reflections with I > 2σ(I) |
Tmin = 0.957, Tmax = 0.971 | Rint = 0.059 |
9446 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 0 restraints |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.17 | Δρmax = 0.37 e Å−3 |
2437 reflections | Δρmin = −0.26 e Å−3 |
239 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 | 0.3040 (4) | 0.30323 (16) | 0.11757 (11) | 0.0630 (7) | |
O2 | 0.2403 (7) | 0.1667 (2) | 0.07470 (17) | 0.1242 (17) | |
O3 | 0.3461 (4) | 0.48147 (15) | 0.18108 (10) | 0.0544 (6) | |
H3 | 0.3806 | 0.4496 | 0.1475 | 0.082* | |
O4 | 0.7636 (5) | 0.29845 (19) | 0.60324 (13) | 0.0794 (8) | |
C1 | 0.6368 (5) | 0.3314 (2) | 0.20925 (15) | 0.0481 (7) | |
H1A | 0.6389 | 0.3573 | 0.1615 | 0.058* | |
H1B | 0.7636 | 0.3138 | 0.2213 | 0.058* | |
C2 | 0.5145 (5) | 0.2454 (2) | 0.20878 (16) | 0.0548 (8) | |
H2A | 0.5619 | 0.2023 | 0.1736 | 0.066* | |
H2B | 0.5204 | 0.2159 | 0.2552 | 0.066* | |
C3 | 0.3140 (5) | 0.2686 (2) | 0.19154 (16) | 0.0531 (8) | |
H3A | 0.2365 | 0.2134 | 0.1962 | 0.064* | |
C4 | 0.2399 (4) | 0.3433 (2) | 0.23997 (15) | 0.0473 (7) | |
H4A | 0.2227 | 0.3175 | 0.2873 | 0.057* | |
H4B | 0.1180 | 0.3618 | 0.2226 | 0.057* | |
C5 | 0.3625 (4) | 0.42965 (19) | 0.24669 (13) | 0.0385 (6) | |
C6 | 0.2822 (4) | 0.4891 (2) | 0.30472 (15) | 0.0438 (6) | |
H6 | 0.1752 | 0.5226 | 0.2940 | 0.053* | |
C7 | 0.3512 (4) | 0.49757 (18) | 0.36930 (14) | 0.0396 (6) | |
H7 | 0.2857 | 0.5326 | 0.4025 | 0.048* | |
C8 | 0.5309 (3) | 0.45324 (17) | 0.39208 (12) | 0.0316 (5) | |
H8 | 0.6304 | 0.4995 | 0.3902 | 0.038* | |
C9 | 0.5828 (4) | 0.37321 (18) | 0.34103 (13) | 0.0334 (5) | |
H9 | 0.4852 | 0.3266 | 0.3469 | 0.040* | |
C10 | 0.5714 (4) | 0.40595 (18) | 0.26191 (13) | 0.0358 (6) | |
C11 | 0.7666 (4) | 0.3270 (2) | 0.36250 (15) | 0.0477 (7) | |
H11A | 0.8686 | 0.3696 | 0.3544 | 0.057* | |
H11B | 0.7869 | 0.2738 | 0.3322 | 0.057* | |
C12 | 0.7699 (5) | 0.2960 (2) | 0.44137 (15) | 0.0495 (8) | |
H12A | 0.6788 | 0.2475 | 0.4487 | 0.059* | |
H12B | 0.8923 | 0.2719 | 0.4533 | 0.059* | |
C13 | 0.7241 (4) | 0.37802 (19) | 0.48968 (13) | 0.0393 (6) | |
C14 | 0.5262 (4) | 0.41171 (17) | 0.46729 (13) | 0.0334 (6) | |
H14 | 0.4524 | 0.3553 | 0.4623 | 0.040* | |
C15 | 0.4424 (4) | 0.4606 (2) | 0.53111 (13) | 0.0420 (6) | |
H15 | 0.3062 | 0.4661 | 0.5337 | 0.050* | |
C16 | 0.5460 (4) | 0.4216 (2) | 0.59609 (14) | 0.0479 (7) | |
H16 | 0.4739 | 0.4039 | 0.6384 | 0.057* | |
C17 | 0.6908 (5) | 0.3584 (2) | 0.56908 (15) | 0.0482 (7) | |
C18 | 0.8868 (4) | 0.4478 (3) | 0.48569 (17) | 0.0540 (8) | |
H18A | 0.9279 | 0.4626 | 0.5331 | 0.081* | |
H18B | 0.8449 | 0.5028 | 0.4622 | 0.081* | |
H18C | 0.9884 | 0.4214 | 0.4593 | 0.081* | |
C19 | 0.6941 (4) | 0.4917 (2) | 0.25053 (15) | 0.0486 (7) | |
H19A | 0.6896 | 0.5095 | 0.2012 | 0.073* | |
H19B | 0.8206 | 0.4778 | 0.2636 | 0.073* | |
H19C | 0.6485 | 0.5411 | 0.2797 | 0.073* | |
C20 | 0.5571 (5) | 0.5230 (2) | 0.57580 (15) | 0.0520 (8) | |
H20A | 0.4920 | 0.5667 | 0.6059 | 0.062* | |
H20B | 0.6737 | 0.5453 | 0.5559 | 0.062* | |
C21 | 0.2665 (6) | 0.2466 (2) | 0.06563 (18) | 0.0650 (10) | |
C22 | 0.2613 (7) | 0.2936 (3) | −0.00473 (18) | 0.0801 (13) | |
H22A | 0.2474 | 0.2487 | −0.0419 | 0.120* | |
H22B | 0.3755 | 0.3270 | −0.0117 | 0.120* | |
H22C | 0.1578 | 0.3355 | −0.0060 | 0.120* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0952 (18) | 0.0565 (12) | 0.0374 (10) | −0.0129 (14) | −0.0124 (12) | −0.0032 (9) |
O2 | 0.236 (5) | 0.0564 (17) | 0.0799 (19) | −0.005 (2) | −0.055 (3) | −0.0110 (15) |
O3 | 0.0732 (15) | 0.0544 (12) | 0.0357 (10) | 0.0020 (11) | −0.0109 (10) | 0.0095 (9) |
O4 | 0.104 (2) | 0.0818 (17) | 0.0527 (14) | 0.0325 (16) | −0.0088 (14) | 0.0228 (13) |
C1 | 0.0591 (18) | 0.0529 (17) | 0.0323 (13) | 0.0073 (15) | 0.0072 (13) | −0.0005 (12) |
C2 | 0.085 (2) | 0.0410 (16) | 0.0381 (14) | 0.0076 (17) | 0.0014 (15) | −0.0057 (12) |
C3 | 0.075 (2) | 0.0442 (15) | 0.0402 (15) | −0.0139 (16) | −0.0062 (15) | −0.0001 (12) |
C4 | 0.0478 (17) | 0.0592 (18) | 0.0350 (13) | −0.0089 (14) | −0.0037 (12) | 0.0012 (12) |
C5 | 0.0430 (15) | 0.0430 (14) | 0.0295 (12) | 0.0001 (12) | −0.0034 (11) | 0.0060 (10) |
C6 | 0.0413 (14) | 0.0465 (15) | 0.0437 (14) | 0.0107 (13) | −0.0089 (12) | 0.0013 (12) |
C7 | 0.0418 (14) | 0.0388 (14) | 0.0382 (13) | 0.0113 (12) | 0.0003 (12) | −0.0013 (11) |
C8 | 0.0330 (12) | 0.0321 (12) | 0.0297 (11) | −0.0001 (10) | −0.0005 (10) | 0.0000 (10) |
C9 | 0.0365 (13) | 0.0337 (12) | 0.0299 (11) | 0.0000 (11) | 0.0019 (10) | 0.0019 (10) |
C10 | 0.0414 (14) | 0.0370 (13) | 0.0291 (12) | −0.0007 (11) | 0.0036 (11) | 0.0025 (10) |
C11 | 0.0537 (17) | 0.0495 (16) | 0.0399 (14) | 0.0154 (14) | 0.0015 (14) | −0.0004 (12) |
C12 | 0.0561 (19) | 0.0487 (16) | 0.0437 (15) | 0.0211 (15) | −0.0045 (14) | 0.0039 (13) |
C13 | 0.0400 (13) | 0.0415 (14) | 0.0363 (13) | 0.0065 (12) | −0.0066 (11) | 0.0032 (11) |
C14 | 0.0329 (12) | 0.0369 (13) | 0.0302 (12) | −0.0014 (10) | −0.0020 (10) | −0.0004 (10) |
C15 | 0.0395 (14) | 0.0560 (16) | 0.0305 (12) | 0.0006 (13) | −0.0016 (12) | −0.0008 (12) |
C16 | 0.0522 (17) | 0.0620 (18) | 0.0294 (13) | −0.0018 (15) | −0.0038 (12) | 0.0013 (12) |
C17 | 0.0529 (16) | 0.0534 (17) | 0.0383 (14) | −0.0017 (15) | −0.0109 (13) | 0.0060 (13) |
C18 | 0.0366 (15) | 0.072 (2) | 0.0537 (17) | −0.0035 (14) | −0.0084 (13) | 0.0048 (16) |
C19 | 0.0515 (17) | 0.0524 (16) | 0.0418 (14) | −0.0116 (14) | 0.0065 (13) | 0.0079 (13) |
C20 | 0.0631 (18) | 0.0525 (17) | 0.0403 (15) | 0.0057 (16) | −0.0057 (14) | −0.0125 (13) |
C21 | 0.090 (3) | 0.0481 (18) | 0.0573 (19) | 0.0094 (19) | −0.0220 (19) | −0.0121 (15) |
C22 | 0.114 (3) | 0.083 (3) | 0.0432 (17) | 0.017 (3) | −0.018 (2) | −0.0103 (18) |
O1—C21 | 1.303 (4) | C10—C19 | 1.540 (4) |
O1—C3 | 1.476 (4) | C11—C12 | 1.545 (4) |
O2—C21 | 1.188 (4) | C11—H11A | 0.9700 |
O3—C5 | 1.446 (3) | C11—H11B | 0.9700 |
O3—H3 | 0.8200 | C12—C13 | 1.533 (4) |
O4—C17 | 1.200 (4) | C12—H12A | 0.9700 |
C1—C2 | 1.527 (5) | C12—H12B | 0.9700 |
C1—C10 | 1.539 (4) | C13—C17 | 1.533 (4) |
C1—H1A | 0.9700 | C13—C18 | 1.546 (4) |
C1—H1B | 0.9700 | C13—C14 | 1.557 (4) |
C2—C3 | 1.510 (5) | C14—C15 | 1.515 (4) |
C2—H2A | 0.9700 | C14—H14 | 0.9800 |
C2—H2B | 0.9700 | C15—C20 | 1.483 (4) |
C3—C4 | 1.511 (4) | C15—C16 | 1.534 (4) |
C3—H3A | 0.9800 | C15—H15 | 0.9800 |
C4—C5 | 1.537 (4) | C16—C17 | 1.475 (5) |
C4—H4A | 0.9700 | C16—C20 | 1.524 (4) |
C4—H4B | 0.9700 | C16—H16 | 0.9800 |
C5—C6 | 1.503 (4) | C18—H18A | 0.9599 |
C5—C10 | 1.561 (4) | C18—H18B | 0.9599 |
C6—C7 | 1.313 (4) | C18—H18C | 0.9599 |
C6—H6 | 0.9300 | C19—H19A | 0.9599 |
C7—C8 | 1.501 (3) | C19—H19B | 0.9599 |
C7—H7 | 0.9300 | C19—H19C | 0.9599 |
C8—C14 | 1.533 (3) | C20—H20A | 0.9700 |
C8—C9 | 1.551 (3) | C20—H20B | 0.9700 |
C8—H8 | 0.9800 | C21—C22 | 1.485 (5) |
C9—C11 | 1.532 (4) | C22—H22A | 0.9599 |
C9—C10 | 1.559 (3) | C22—H22B | 0.9599 |
C9—H9 | 0.9800 | C22—H22C | 0.9599 |
C21—O1—C3 | 119.7 (3) | H11A—C11—H11B | 107.8 |
C5—O3—H3 | 109.5 | C13—C12—C11 | 109.5 (2) |
C2—C1—C10 | 114.0 (2) | C13—C12—H12A | 109.8 |
C2—C1—H1A | 108.8 | C11—C12—H12A | 109.8 |
C10—C1—H1A | 108.8 | C13—C12—H12B | 109.8 |
C2—C1—H1B | 108.8 | C11—C12—H12B | 109.8 |
C10—C1—H1B | 108.8 | H12A—C12—H12B | 108.2 |
H1A—C1—H1B | 107.7 | C12—C13—C17 | 117.4 (2) |
C3—C2—C1 | 111.3 (3) | C12—C13—C18 | 108.7 (3) |
C3—C2—H2A | 109.4 | C17—C13—C18 | 106.6 (2) |
C1—C2—H2A | 109.4 | C12—C13—C14 | 106.3 (2) |
C3—C2—H2B | 109.4 | C17—C13—C14 | 100.3 (2) |
C1—C2—H2B | 109.4 | C18—C13—C14 | 117.8 (2) |
H2A—C2—H2B | 108.0 | C15—C14—C8 | 123.3 (2) |
O1—C3—C2 | 108.9 (3) | C15—C14—C13 | 107.2 (2) |
O1—C3—C4 | 107.5 (3) | C8—C14—C13 | 110.6 (2) |
C2—C3—C4 | 111.5 (3) | C15—C14—H14 | 104.7 |
O1—C3—H3A | 109.6 | C8—C14—H14 | 104.7 |
C2—C3—H3A | 109.6 | C13—C14—H14 | 104.7 |
C4—C3—H3A | 109.6 | C20—C15—C14 | 120.9 (3) |
C3—C4—C5 | 115.8 (3) | C20—C15—C16 | 60.7 (2) |
C3—C4—H4A | 108.3 | C14—C15—C16 | 105.2 (2) |
C5—C4—H4A | 108.3 | C20—C15—H15 | 118.2 |
C3—C4—H4B | 108.3 | C14—C15—H15 | 118.2 |
C5—C4—H4B | 108.3 | C16—C15—H15 | 118.2 |
H4A—C4—H4B | 107.4 | C17—C16—C20 | 118.7 (3) |
O3—C5—C6 | 106.5 (2) | C17—C16—C15 | 107.3 (2) |
O3—C5—C4 | 108.0 (2) | C20—C16—C15 | 58.02 (19) |
C6—C5—C4 | 108.1 (2) | C17—C16—H16 | 118.9 |
O3—C5—C10 | 110.3 (2) | C20—C16—H16 | 118.9 |
C6—C5—C10 | 111.2 (2) | C15—C16—H16 | 118.9 |
C4—C5—C10 | 112.4 (2) | O4—C17—C16 | 125.1 (3) |
C7—C6—C5 | 125.2 (3) | O4—C17—C13 | 125.8 (3) |
C7—C6—H6 | 117.4 | C16—C17—C13 | 109.0 (2) |
C5—C6—H6 | 117.4 | C13—C18—H18A | 109.5 |
C6—C7—C8 | 123.0 (2) | C13—C18—H18B | 109.5 |
C6—C7—H7 | 118.5 | H18A—C18—H18B | 109.5 |
C8—C7—H7 | 118.5 | C13—C18—H18C | 109.5 |
C7—C8—C14 | 114.3 (2) | H18A—C18—H18C | 109.5 |
C7—C8—C9 | 110.6 (2) | H18B—C18—H18C | 109.5 |
C14—C8—C9 | 106.03 (19) | C10—C19—H19A | 109.5 |
C7—C8—H8 | 108.6 | C10—C19—H19B | 109.5 |
C14—C8—H8 | 108.6 | H19A—C19—H19B | 109.5 |
C9—C8—H8 | 108.6 | C10—C19—H19C | 109.5 |
C11—C9—C8 | 111.9 (2) | H19A—C19—H19C | 109.5 |
C11—C9—C10 | 115.4 (2) | H19B—C19—H19C | 109.5 |
C8—C9—C10 | 110.1 (2) | C15—C20—C16 | 61.3 (2) |
C11—C9—H9 | 106.2 | C15—C20—H20A | 117.6 |
C8—C9—H9 | 106.2 | C16—C20—H20A | 117.6 |
C10—C9—H9 | 106.2 | C15—C20—H20B | 117.6 |
C1—C10—C19 | 107.9 (2) | C16—C20—H20B | 117.6 |
C1—C10—C9 | 112.2 (2) | H20A—C20—H20B | 114.7 |
C19—C10—C9 | 110.4 (2) | O2—C21—O1 | 122.9 (3) |
C1—C10—C5 | 109.3 (2) | O2—C21—C22 | 124.9 (3) |
C19—C10—C5 | 110.0 (2) | O1—C21—C22 | 112.1 (3) |
C9—C10—C5 | 106.9 (2) | C21—C22—H22A | 109.5 |
C9—C11—C12 | 113.1 (2) | C21—C22—H22B | 109.5 |
C9—C11—H11A | 109.0 | H22A—C22—H22B | 109.5 |
C12—C11—H11A | 109.0 | C21—C22—H22C | 109.5 |
C9—C11—H11B | 109.0 | H22A—C22—H22C | 109.5 |
C12—C11—H11B | 109.0 | H22B—C22—H22C | 109.5 |
C10—C1—C2—C3 | 57.5 (3) | C8—C9—C11—C12 | 53.0 (3) |
C21—O1—C3—C2 | 93.8 (4) | C10—C9—C11—C12 | −180.0 (2) |
C21—O1—C3—C4 | −145.3 (3) | C9—C11—C12—C13 | −54.7 (3) |
C1—C2—C3—O1 | 65.6 (3) | C11—C12—C13—C17 | 170.8 (3) |
C1—C2—C3—C4 | −52.8 (3) | C11—C12—C13—C18 | −68.0 (3) |
O1—C3—C4—C5 | −69.1 (3) | C11—C12—C13—C14 | 59.7 (3) |
C2—C3—C4—C5 | 50.1 (3) | C7—C8—C14—C15 | −44.5 (3) |
C3—C4—C5—O3 | 73.5 (3) | C9—C8—C14—C15 | −166.7 (2) |
C3—C4—C5—C6 | −171.6 (2) | C7—C8—C14—C13 | −173.2 (2) |
C3—C4—C5—C10 | −48.5 (3) | C9—C8—C14—C13 | 64.7 (2) |
O3—C5—C6—C7 | −140.1 (3) | C12—C13—C14—C15 | 155.2 (2) |
C4—C5—C6—C7 | 104.0 (3) | C17—C13—C14—C15 | 32.5 (3) |
C10—C5—C6—C7 | −19.9 (4) | C18—C13—C14—C15 | −82.6 (3) |
C5—C6—C7—C8 | 4.7 (5) | C12—C13—C14—C8 | −67.8 (3) |
C6—C7—C8—C14 | −139.1 (3) | C17—C13—C14—C8 | 169.4 (2) |
C6—C7—C8—C9 | −19.5 (4) | C18—C13—C14—C8 | 54.3 (3) |
C7—C8—C9—C11 | 179.5 (2) | C8—C14—C15—C20 | −88.7 (3) |
C14—C8—C9—C11 | −56.0 (3) | C13—C14—C15—C20 | 41.4 (3) |
C7—C8—C9—C10 | 49.7 (3) | C8—C14—C15—C16 | −153.3 (2) |
C14—C8—C9—C10 | 174.2 (2) | C13—C14—C15—C16 | −23.2 (3) |
C2—C1—C10—C19 | −173.9 (2) | C20—C15—C16—C17 | −113.5 (3) |
C2—C1—C10—C9 | 64.2 (3) | C14—C15—C16—C17 | 3.7 (3) |
C2—C1—C10—C5 | −54.3 (3) | C14—C15—C16—C20 | 117.2 (3) |
C11—C9—C10—C1 | 47.5 (3) | C20—C16—C17—O4 | 138.3 (3) |
C8—C9—C10—C1 | 175.4 (2) | C15—C16—C17—O4 | −159.2 (3) |
C11—C9—C10—C19 | −73.0 (3) | C20—C16—C17—C13 | −44.9 (3) |
C8—C9—C10—C19 | 55.0 (3) | C15—C16—C17—C13 | 17.6 (3) |
C11—C9—C10—C5 | 167.3 (2) | C12—C13—C17—O4 | 31.7 (5) |
C8—C9—C10—C5 | −64.8 (3) | C18—C13—C17—O4 | −90.5 (4) |
O3—C5—C10—C1 | −72.4 (3) | C14—C13—C17—O4 | 146.2 (3) |
C6—C5—C10—C1 | 169.7 (2) | C12—C13—C17—C16 | −145.0 (3) |
C4—C5—C10—C1 | 48.3 (3) | C18—C13—C17—C16 | 92.7 (3) |
O3—C5—C10—C19 | 46.0 (3) | C14—C13—C17—C16 | −30.5 (3) |
C6—C5—C10—C19 | −72.0 (3) | C14—C15—C20—C16 | −90.8 (3) |
C4—C5—C10—C19 | 166.7 (2) | C17—C16—C20—C15 | 93.3 (3) |
O3—C5—C10—C9 | 165.9 (2) | C3—O1—C21—O2 | −0.4 (7) |
C6—C5—C10—C9 | 48.0 (3) | C3—O1—C21—C22 | 179.7 (3) |
C4—C5—C10—C9 | −73.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1 | 0.82 | 2.27 | 2.868 (3) | 130 |
C18—H18B···O2i | 0.96 | 2.55 | 3.498 (4) | 168 |
C9—H9···O4ii | 0.98 | 2.59 | 3.542 (3) | 165 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1/2, −y+1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C22H30O4 |
Mr | 358.46 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 7.160 (4), 14.541 (8), 18.733 (10) |
V (Å3) | 1950.4 (18) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.40 × 0.35 × 0.25 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1997) |
Tmin, Tmax | 0.957, 0.971 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9446, 2437, 2036 |
Rint | 0.059 |
(sin θ/λ)max (Å−1) | 0.639 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.150, 1.17 |
No. of reflections | 2437 |
No. of parameters | 239 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.37, −0.26 |
Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Version 1.05; Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O1 | 0.82 | 2.27 | 2.868 (3) | 130.3 |
C18—H18B···O2i | 0.96 | 2.55 | 3.498 (4) | 167.5 |
C9—H9···O4ii | 0.98 | 2.59 | 3.542 (3) | 164.5 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x−1/2, −y+1/2, −z+1. |
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Drospirenone is a new contraceptive drug with the antimineralocorticoid and antiandrogenic properties (Muhn et al., 1995). In our attempts to synthesize this drug, the title compound, (I), was obtained as an intermediate by the reductive dechlorination of, 3β-acetoxy-7α-chloro-5,6β-epoxy-15β,16β-methylene-5β-androstan-17-one, (II). 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 (1.524 (4) versus 1.484 (3) 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) reported previously (Zhou et al., 2007). The difference in these bond lengths might be caused by a hyperconjugation interacton between the C=O π-bonding and C16—C20 σ-bonding orbitals. However, in the analogous structure of 3 b-Acetoxy-17,17-ethylenedioxy-15b,16b-methylene-5-androsten-7 b-ol these bond lenghts are almost equal (1.499 (6) and 1.493 (6) Å) (Zhou et al., 2006).
In the steroid skeleton, the ring A and ring C show slightly distorted chair conformations, ring B shows a closely symmetric half-chair conformation and ring D is in an an envelope conformation. In ring B, atom C9 and atom C10 deviate by -0.402 (4)Å and 0.410 (4)Å from the mean plane calculated through the ring C5—C8, respectively. In ring D, C13 deviates by 0.513 (4)Å from the mean plane of C14—C17, which makes a dihedral angle of 64.6 (2)° with the cyclopropyl ring C15/C16/C20. In the structure an intramolecular O—H···O hydrogen bond is found (Table 1). In addition, two weak intermolecular C—H···O hydrogen bonds are also observed (Table 1.).