organic compounds
(3S,7R)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one.
aBAM Federal Institute for Materials Research and Testing, Department of Analytical Chemistry, Reference Materials, Richard-Willstätter-Strasse 11, D-12489 Berlin, Germany
*Correspondence e-mail: sarah.drzymala@bam.de
The 18H26O5, which is known as α-zearalanol, contains two molecules having the same conformation, with a r.m.s. deviation of less than 0.03 Å for all non-H atoms. In each independent molecule, an intramolecular O—H⋯O hydrogen bond stabilizes the molecular conformation. In the crystal, O—H⋯O hydrogen bonds link the molecules, forming infinite chains along [110] and [1-10].
of the title compound, CRelated literature
For the chemical preparation of α-zearalanol, see: Urry et al. (1966). For its natural occurrence as a metabolite, see: Baldwin et al. (1983) and for its use as an animal growth promoter, see: Wang & Wang (2007). For the crystal structures of related derivatives, see: Panneerselvam et al. (1996); Gelo-Pujić et al. (1994); Zhao et al. (2008); Köppen et al. (2012); Drzymala et al. (2012).
Experimental
Crystal data
|
Refinement
|
Data collection: APEX2 (Bruker, 2001); cell SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536812041141/fj2595sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041141/fj2595Isup2.hkl
α-Zearalanol was obtained from Sigma-Aldrich Chemie GmbH (Germany, purity 97.0%). 5 mg (15.5 µmol) were weighed in a 1.5 ml HPLC glass vial and solved in 0.6 ml diethyl ether. Subsequently, 0.2 ml of n-hexane were added. Colorless crystals of the title compound were formed after 14 days of slow solvent evaporation at room temperature.
All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic 0.98 Å, Uiso = 1.2Ueq (C) for CH, 0.97 Å, Uiso = 1.2Ueq (C) for CH2, 0.96 Å, Uiso = 1.5Ueq (C) for CH3 atoms, and 0.82 Å, Uiso = 1.5Ueq (C) for hydroxyl group of O5. The hydrogen atoms from the other hydroxyl groups were treated independently. In the absence of significant
effects 3785 Friedel pairs were merged. The has not been determined by anomalous-dispersion effects in diffraction measurements of the crystal. The has been assigned by reference to an unchanging chiral centre in the synthetic procedure.Data collection: APEX2 (Bruker, 2001); cell
SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. : ORTEP representation of the title compound with atomic labeling shown with 30% probability displacement ellipsoids. | |
Fig. 2. : View of the unit cell of the title compound, showing the hydrogen-bonded chains of the two independent molecules. Hydrogen bonds are drawn as dashed red lines. | |
Fig. 3. : View of the unit cell of the title compound, showing the two chains with planes of the basevectors. Turquoise for [1 1 0] and lime for [1 - 1 0]. Hydrogen bonds are drawn as dashed red lines. | |
Fig. 4. : The difference in conformation between the known β-Zearalanol (yellow, Gelo-Pujić et al., 1994) and the title compound. |
C18H26O5 | Z = 2 |
Mr = 322.39 | F(000) = 348 |
Triclinic, P1 | Dx = 1.238 Mg m−3 |
a = 5.0734 (11) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.618 (2) Å | Cell parameters from 6563 reflections |
c = 14.718 (3) Å | θ = 2.3–26.4° |
α = 87.388 (13)° | µ = 0.09 mm−1 |
β = 86.595 (15)° | T = 296 K |
γ = 89.780 (15)° | Block, colourless |
V = 865.0 (3) Å3 | 0.43 × 0.22 × 0.10 mm |
Bruker APEXII CCD diffractometer | 4264 independent reflections |
Radiation source: fine-focus sealed tube | 3421 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.095 |
ϕ and ω scans | θmax = 28.3°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −6→6 |
Tmin = 0.186, Tmax = 0.350 | k = −15→15 |
19642 measured reflections | l = −19→19 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.147 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0803P)2] where P = (Fo2 + 2Fc2)/3 |
4264 reflections | (Δ/σ)max < 0.001 |
431 parameters | Δρmax = 0.24 e Å−3 |
7 restraints | Δρmin = −0.16 e Å−3 |
C18H26O5 | γ = 89.780 (15)° |
Mr = 322.39 | V = 865.0 (3) Å3 |
Triclinic, P1 | Z = 2 |
a = 5.0734 (11) Å | Mo Kα radiation |
b = 11.618 (2) Å | µ = 0.09 mm−1 |
c = 14.718 (3) Å | T = 296 K |
α = 87.388 (13)° | 0.43 × 0.22 × 0.10 mm |
β = 86.595 (15)° |
Bruker APEXII CCD diffractometer | 4264 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | 3421 reflections with I > 2σ(I) |
Tmin = 0.186, Tmax = 0.350 | Rint = 0.095 |
19642 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 7 restraints |
wR(F2) = 0.147 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.95 | Δρmax = 0.24 e Å−3 |
4264 reflections | Δρmin = −0.16 e Å−3 |
431 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 | −0.1448 (4) | 0.89233 (14) | 0.65863 (11) | 0.0465 (4) | |
O2 | 0.0413 (4) | 0.99572 (16) | 0.76207 (12) | 0.0555 (5) | |
O3 | −0.3004 (5) | 0.45828 (17) | 0.45181 (16) | 0.0618 (6) | |
O4 | 0.2440 (5) | 1.34395 (16) | 0.41989 (13) | 0.0570 (5) | |
O5 | 0.3693 (4) | 1.15285 (17) | 0.70652 (13) | 0.0578 (5) | |
H5A | 0.3015 | 1.1038 | 0.7423 | 0.087* | |
C1 | −0.0231 (5) | 0.9872 (2) | 0.68358 (16) | 0.0409 (5) | |
C2 | −0.4309 (7) | 0.8317 (3) | 0.7915 (2) | 0.0683 (8) | |
H2A | −0.3901 | 0.9000 | 0.8222 | 0.102* | |
H2B | −0.4694 | 0.7698 | 0.8356 | 0.102* | |
H2C | −0.5817 | 0.8459 | 0.7561 | 0.102* | |
C3 | −0.1985 (5) | 0.7995 (2) | 0.72962 (16) | 0.0435 (6) | |
H3B | −0.0429 | 0.7882 | 0.7654 | 0.052* | |
C4 | −0.2456 (5) | 0.6918 (2) | 0.67829 (18) | 0.0469 (6) | |
H4B | −0.3192 | 0.6329 | 0.7211 | 0.056* | |
H4C | −0.3763 | 0.7093 | 0.6341 | 0.056* | |
C5 | −0.0035 (6) | 0.6437 (2) | 0.6292 (2) | 0.0526 (7) | |
H5B | 0.1227 | 0.6215 | 0.6738 | 0.063* | |
H5C | 0.0767 | 0.7042 | 0.5893 | 0.063* | |
C6 | −0.0549 (7) | 0.5390 (2) | 0.5722 (2) | 0.0580 (7) | |
H6A | 0.1135 | 0.5081 | 0.5500 | 0.070* | |
H6B | −0.1424 | 0.4797 | 0.6115 | 0.070* | |
C7 | −0.2229 (6) | 0.5653 (2) | 0.49103 (19) | 0.0493 (6) | |
H7A | −0.3846 | 0.6033 | 0.5140 | 0.059* | |
C8 | −0.0915 (6) | 0.6456 (2) | 0.41628 (19) | 0.0535 (7) | |
H8A | 0.0351 | 0.6937 | 0.4435 | 0.064* | |
H8B | 0.0053 | 0.5991 | 0.3725 | 0.064* | |
C9 | −0.2828 (6) | 0.7229 (2) | 0.36581 (18) | 0.0563 (7) | |
H9A | −0.1933 | 0.7532 | 0.3097 | 0.068* | |
H9B | −0.4294 | 0.6763 | 0.3493 | 0.068* | |
C10 | −0.3925 (6) | 0.8235 (2) | 0.41891 (19) | 0.0482 (6) | |
H10A | −0.4831 | 0.7935 | 0.4749 | 0.058* | |
H10B | −0.5218 | 0.8637 | 0.3833 | 0.058* | |
C11 | −0.1827 (5) | 0.9100 (2) | 0.44291 (17) | 0.0444 (6) | |
H11A | −0.0530 | 0.8701 | 0.4787 | 0.053* | |
H11B | −0.0925 | 0.9408 | 0.3871 | 0.053* | |
C12 | −0.2995 (5) | 1.0093 (2) | 0.49636 (17) | 0.0411 (5) | |
H12A | −0.4017 | 0.9785 | 0.5497 | 0.049* | |
H12B | −0.4182 | 1.0532 | 0.4587 | 0.049* | |
C13 | −0.0089 (5) | 1.1798 (2) | 0.46580 (17) | 0.0438 (6) | |
H13A | −0.0918 | 1.1891 | 0.4113 | 0.053* | |
C14 | 0.1884 (5) | 1.2568 (2) | 0.48410 (17) | 0.0437 (6) | |
C15 | 0.3129 (6) | 1.2462 (2) | 0.56527 (18) | 0.0457 (6) | |
H15A | 0.4448 | 1.2977 | 0.5775 | 0.055* | |
C16 | 0.2384 (5) | 1.1575 (2) | 0.62849 (16) | 0.0415 (5) | |
C17 | 0.0383 (5) | 1.07732 (19) | 0.61033 (16) | 0.0372 (5) | |
C18 | −0.0857 (5) | 1.08946 (19) | 0.52648 (16) | 0.0377 (5) | |
O1' | 0.5442 (4) | 0.37345 (14) | 0.94217 (11) | 0.0462 (4) | |
O2' | 0.3680 (4) | 0.48975 (16) | 0.83705 (12) | 0.0549 (5) | |
O3' | 0.6823 (5) | −0.08133 (17) | 1.15210 (15) | 0.0602 (5) | |
O4' | 0.1425 (4) | 0.79967 (16) | 1.17536 (14) | 0.0567 (5) | |
O5' | 0.0323 (4) | 0.63890 (17) | 0.89001 (13) | 0.0608 (5) | |
H5'A | 0.1034 | 0.5941 | 0.8547 | 0.091* | |
C1' | 0.4249 (5) | 0.4708 (2) | 0.91655 (17) | 0.0414 (5) | |
C2' | 0.8444 (7) | 0.3297 (3) | 0.8122 (3) | 0.0726 (9) | |
H2'A | 0.8052 | 0.4014 | 0.7807 | 0.109* | |
H2'B | 0.8904 | 0.2729 | 0.7686 | 0.109* | |
H2'C | 0.9897 | 0.3403 | 0.8498 | 0.109* | |
C3' | 0.6061 (5) | 0.2899 (2) | 0.87071 (17) | 0.0436 (6) | |
H3'B | 0.4548 | 0.2832 | 0.8329 | 0.052* | |
C4' | 0.6511 (6) | 0.1755 (2) | 0.92215 (19) | 0.0484 (6) | |
H4'B | 0.7733 | 0.1878 | 0.9690 | 0.058* | |
H4'C | 0.7338 | 0.1224 | 0.8801 | 0.058* | |
C5' | 0.4010 (6) | 0.1196 (2) | 0.96673 (18) | 0.0497 (6) | |
H5'B | 0.2853 | 0.1009 | 0.9194 | 0.060* | |
H5'C | 0.3099 | 0.1750 | 1.0047 | 0.060* | |
C6' | 0.4513 (6) | 0.0096 (2) | 1.02532 (19) | 0.0548 (7) | |
H6'A | 0.2827 | −0.0263 | 1.0432 | 0.066* | |
H6'B | 0.5524 | −0.0437 | 0.9882 | 0.066* | |
C7' | 0.5984 (6) | 0.0283 (2) | 1.11146 (18) | 0.0472 (6) | |
H7'A | 0.7575 | 0.0733 | 1.0933 | 0.057* | |
C8' | 0.4374 (6) | 0.0953 (2) | 1.18242 (19) | 0.0511 (6) | |
H8'A | 0.3308 | 0.0415 | 1.2210 | 0.061* | |
H8'B | 0.3183 | 0.1471 | 1.1514 | 0.061* | |
C9' | 0.6079 (7) | 0.1660 (2) | 1.24287 (19) | 0.0594 (8) | |
H9'A | 0.4982 | 0.1905 | 1.2947 | 0.071* | |
H9'B | 0.7455 | 0.1166 | 1.2660 | 0.071* | |
C10' | 0.7366 (6) | 0.2724 (2) | 1.1937 (2) | 0.0537 (7) | |
H10C | 0.8532 | 0.3073 | 1.2345 | 0.064* | |
H10D | 0.8440 | 0.2479 | 1.1414 | 0.064* | |
C11' | 0.5409 (6) | 0.3635 (2) | 1.16147 (18) | 0.0491 (6) | |
H11C | 0.4388 | 0.3909 | 1.2140 | 0.059* | |
H11D | 0.4194 | 0.3281 | 1.1227 | 0.059* | |
C12' | 0.6742 (5) | 0.4672 (2) | 1.10867 (18) | 0.0440 (6) | |
H12C | 0.7903 | 0.5050 | 1.1480 | 0.053* | |
H12D | 0.7810 | 0.4401 | 1.0571 | 0.053* | |
C13' | 0.3928 (6) | 0.6373 (2) | 1.13423 (18) | 0.0456 (6) | |
H13B | 0.4704 | 0.6401 | 1.1898 | 0.055* | |
C14' | 0.1995 (5) | 0.7179 (2) | 1.11290 (17) | 0.0444 (6) | |
C15' | 0.0797 (6) | 0.7162 (2) | 1.03129 (18) | 0.0450 (6) | |
H15B | −0.0523 | 0.7690 | 1.0180 | 0.054* | |
C16' | 0.1590 (5) | 0.6347 (2) | 0.96934 (16) | 0.0417 (6) | |
C17' | 0.3551 (5) | 0.55111 (19) | 0.98913 (16) | 0.0376 (5) | |
C18' | 0.4720 (5) | 0.55347 (19) | 1.07492 (16) | 0.0389 (5) | |
H4A | 0.388 (4) | 1.371 (3) | 0.431 (2) | 0.073 (11)* | |
H3'A | 0.543 (5) | −0.113 (4) | 1.169 (3) | 0.108 (17)* | |
H3A | −0.175 (5) | 0.418 (3) | 0.436 (3) | 0.087 (14)* | |
H4'A | −0.005 (5) | 0.823 (4) | 1.163 (4) | 0.13 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0625 (12) | 0.0364 (9) | 0.0408 (9) | −0.0108 (8) | −0.0077 (8) | 0.0041 (7) |
O2 | 0.0760 (13) | 0.0506 (10) | 0.0408 (9) | −0.0087 (10) | −0.0120 (9) | −0.0022 (8) |
O3 | 0.0717 (16) | 0.0379 (11) | 0.0762 (14) | −0.0139 (11) | −0.0031 (12) | −0.0090 (9) |
O4 | 0.0772 (15) | 0.0375 (10) | 0.0557 (11) | −0.0172 (10) | −0.0011 (11) | 0.0022 (8) |
O5 | 0.0702 (13) | 0.0535 (11) | 0.0519 (11) | −0.0147 (10) | −0.0194 (10) | −0.0050 (9) |
C1 | 0.0458 (14) | 0.0372 (12) | 0.0393 (13) | 0.0009 (10) | 0.0025 (10) | −0.0048 (9) |
C2 | 0.066 (2) | 0.0638 (19) | 0.072 (2) | −0.0032 (16) | 0.0199 (16) | −0.0031 (15) |
C3 | 0.0473 (14) | 0.0422 (13) | 0.0400 (12) | −0.0025 (11) | −0.0010 (10) | 0.0090 (10) |
C4 | 0.0490 (15) | 0.0413 (14) | 0.0494 (14) | −0.0106 (11) | −0.0020 (11) | 0.0078 (11) |
C5 | 0.0513 (16) | 0.0489 (15) | 0.0584 (16) | −0.0009 (13) | −0.0098 (13) | −0.0034 (12) |
C6 | 0.072 (2) | 0.0400 (14) | 0.0628 (17) | −0.0007 (13) | −0.0070 (15) | −0.0040 (12) |
C7 | 0.0560 (16) | 0.0319 (12) | 0.0593 (16) | −0.0116 (11) | 0.0059 (13) | −0.0059 (11) |
C8 | 0.0623 (18) | 0.0402 (14) | 0.0568 (16) | −0.0132 (13) | 0.0130 (14) | −0.0098 (12) |
C9 | 0.078 (2) | 0.0482 (15) | 0.0433 (13) | −0.0210 (14) | −0.0054 (13) | −0.0057 (11) |
C10 | 0.0565 (16) | 0.0425 (13) | 0.0466 (13) | −0.0088 (12) | −0.0128 (12) | 0.0004 (10) |
C11 | 0.0509 (15) | 0.0368 (12) | 0.0456 (13) | −0.0098 (11) | −0.0031 (11) | −0.0029 (10) |
C12 | 0.0397 (13) | 0.0377 (12) | 0.0462 (13) | −0.0041 (10) | −0.0068 (10) | 0.0001 (10) |
C13 | 0.0559 (16) | 0.0344 (12) | 0.0420 (13) | −0.0015 (11) | −0.0082 (11) | −0.0033 (10) |
C14 | 0.0554 (15) | 0.0291 (11) | 0.0461 (13) | −0.0034 (11) | 0.0019 (11) | −0.0035 (10) |
C15 | 0.0515 (14) | 0.0356 (12) | 0.0506 (14) | −0.0083 (11) | −0.0005 (11) | −0.0105 (10) |
C16 | 0.0462 (14) | 0.0379 (13) | 0.0413 (13) | −0.0012 (11) | −0.0031 (11) | −0.0091 (10) |
C17 | 0.0438 (13) | 0.0297 (11) | 0.0384 (11) | −0.0005 (10) | −0.0001 (10) | −0.0067 (9) |
C18 | 0.0377 (12) | 0.0324 (11) | 0.0432 (12) | 0.0003 (10) | −0.0024 (10) | −0.0050 (9) |
O1' | 0.0606 (11) | 0.0368 (9) | 0.0418 (9) | 0.0061 (8) | −0.0066 (8) | −0.0057 (7) |
O2' | 0.0787 (14) | 0.0458 (10) | 0.0406 (10) | 0.0043 (9) | −0.0097 (9) | 0.0003 (8) |
O3' | 0.0700 (15) | 0.0376 (10) | 0.0724 (13) | 0.0094 (10) | −0.0038 (11) | 0.0034 (9) |
O4' | 0.0712 (14) | 0.0415 (11) | 0.0567 (11) | 0.0081 (10) | 0.0065 (10) | −0.0081 (8) |
O5' | 0.0785 (14) | 0.0532 (11) | 0.0521 (11) | 0.0131 (10) | −0.0191 (10) | 0.0004 (9) |
C1' | 0.0474 (14) | 0.0343 (12) | 0.0420 (13) | −0.0040 (10) | −0.0006 (11) | 0.0016 (9) |
C2' | 0.070 (2) | 0.0622 (19) | 0.082 (2) | −0.0024 (17) | 0.0238 (18) | −0.0024 (16) |
C3' | 0.0473 (14) | 0.0415 (13) | 0.0417 (12) | −0.0006 (11) | 0.0031 (10) | −0.0074 (10) |
C4' | 0.0502 (15) | 0.0445 (14) | 0.0504 (14) | 0.0071 (12) | 0.0012 (11) | −0.0080 (11) |
C5' | 0.0538 (16) | 0.0470 (15) | 0.0486 (14) | −0.0032 (12) | −0.0060 (12) | −0.0012 (11) |
C6' | 0.0695 (19) | 0.0388 (14) | 0.0564 (16) | −0.0056 (13) | −0.0047 (14) | −0.0040 (12) |
C7' | 0.0563 (16) | 0.0320 (12) | 0.0528 (14) | 0.0023 (11) | 0.0000 (12) | −0.0001 (10) |
C8' | 0.0619 (17) | 0.0403 (13) | 0.0499 (14) | 0.0036 (12) | 0.0029 (12) | 0.0013 (11) |
C9' | 0.093 (2) | 0.0404 (14) | 0.0452 (14) | 0.0140 (15) | −0.0131 (15) | 0.0002 (11) |
C10' | 0.0653 (18) | 0.0387 (13) | 0.0596 (17) | 0.0054 (12) | −0.0225 (14) | −0.0040 (12) |
C11' | 0.0591 (16) | 0.0382 (13) | 0.0500 (14) | 0.0053 (12) | −0.0073 (12) | 0.0019 (11) |
C12' | 0.0495 (15) | 0.0388 (13) | 0.0452 (13) | 0.0012 (11) | −0.0107 (11) | −0.0059 (10) |
C13' | 0.0550 (16) | 0.0367 (13) | 0.0452 (13) | −0.0047 (11) | −0.0045 (11) | −0.0019 (10) |
C14' | 0.0549 (15) | 0.0313 (12) | 0.0452 (13) | −0.0010 (11) | 0.0090 (11) | 0.0015 (10) |
C15' | 0.0498 (15) | 0.0321 (12) | 0.0521 (14) | 0.0041 (11) | 0.0010 (11) | 0.0045 (10) |
C16' | 0.0492 (15) | 0.0344 (12) | 0.0406 (12) | −0.0055 (11) | −0.0030 (10) | 0.0074 (10) |
C17' | 0.0413 (13) | 0.0309 (11) | 0.0402 (12) | −0.0052 (10) | −0.0010 (10) | 0.0017 (9) |
C18' | 0.0409 (13) | 0.0298 (12) | 0.0456 (13) | −0.0046 (10) | −0.0033 (10) | 0.0024 (10) |
O1—C1 | 1.341 (3) | O1'—C1' | 1.331 (3) |
O1—C3 | 1.482 (3) | O1'—C3' | 1.483 (3) |
O2—C1 | 1.227 (3) | O2'—C1' | 1.232 (3) |
O3—C7 | 1.460 (3) | O3'—C7' | 1.456 (3) |
O3—H3A | 0.818 (10) | O3'—H3'A | 0.821 (10) |
O4—C14 | 1.372 (3) | O4'—C14' | 1.370 (3) |
O4—H4A | 0.826 (10) | O4'—H4'A | 0.821 (10) |
O5—C16 | 1.359 (3) | O5'—C16' | 1.365 (3) |
O5—H5A | 0.8200 | O5'—H5'A | 0.8200 |
C1—C17 | 1.489 (3) | C1'—C17' | 1.476 (3) |
C2—C3 | 1.503 (4) | C2'—C3' | 1.504 (4) |
C2—H2A | 0.9600 | C2'—H2'A | 0.9600 |
C2—H2B | 0.9600 | C2'—H2'B | 0.9600 |
C2—H2C | 0.9600 | C2'—H2'C | 0.9600 |
C3—C4 | 1.517 (4) | C3'—C4' | 1.523 (4) |
C3—H3B | 0.9800 | C3'—H3'B | 0.9800 |
C4—C5 | 1.507 (4) | C4'—C5' | 1.527 (4) |
C4—H4B | 0.9700 | C4'—H4'B | 0.9700 |
C4—H4C | 0.9700 | C4'—H4'C | 0.9700 |
C5—C6 | 1.540 (4) | C5'—C6' | 1.538 (4) |
C5—H5B | 0.9700 | C5'—H5'B | 0.9700 |
C5—H5C | 0.9700 | C5'—H5'C | 0.9700 |
C6—C7 | 1.527 (4) | C6'—C7' | 1.533 (4) |
C6—H6A | 0.9700 | C6'—H6'A | 0.9700 |
C6—H6B | 0.9700 | C6'—H6'B | 0.9700 |
C7—C8 | 1.532 (4) | C7'—C8' | 1.527 (4) |
C7—H7A | 0.9800 | C7'—H7'A | 0.9800 |
C8—C9 | 1.523 (5) | C8'—C9' | 1.542 (4) |
C8—H8A | 0.9700 | C8'—H8'A | 0.9700 |
C8—H8B | 0.9700 | C8'—H8'B | 0.9700 |
C9—C10 | 1.520 (4) | C9'—C10' | 1.532 (4) |
C9—H9A | 0.9700 | C9'—H9'A | 0.9700 |
C9—H9B | 0.9700 | C9'—H9'B | 0.9700 |
C10—C11 | 1.534 (3) | C10'—C11' | 1.528 (4) |
C10—H10A | 0.9700 | C10'—H10C | 0.9700 |
C10—H10B | 0.9700 | C10'—H10D | 0.9700 |
C11—C12 | 1.524 (3) | C11'—C12' | 1.540 (4) |
C11—H11A | 0.9700 | C11'—H11C | 0.9700 |
C11—H11B | 0.9700 | C11'—H11D | 0.9700 |
C12—C18 | 1.531 (3) | C12'—C18' | 1.520 (3) |
C12—H12A | 0.9700 | C12'—H12C | 0.9700 |
C12—H12B | 0.9700 | C12'—H12D | 0.9700 |
C13—C18 | 1.388 (3) | C13'—C18' | 1.381 (3) |
C13—C14 | 1.391 (4) | C13'—C14' | 1.392 (4) |
C13—H13A | 0.9300 | C13'—H13B | 0.9300 |
C14—C15 | 1.385 (4) | C14'—C15' | 1.379 (4) |
C15—C16 | 1.394 (3) | C15'—C16' | 1.387 (4) |
C15—H15A | 0.9300 | C15'—H15B | 0.9300 |
C16—C17 | 1.425 (3) | C16'—C17' | 1.421 (3) |
C17—C18 | 1.419 (3) | C17'—C18' | 1.428 (3) |
C1—O1—C3 | 117.26 (18) | C1'—O1'—C3' | 116.96 (18) |
C7—O3—H3A | 113 (3) | C7'—O3'—H3'A | 103 (3) |
C14—O4—H4A | 106 (3) | C14'—O4'—H4'A | 104 (4) |
C16—O5—H5A | 109.5 | C16'—O5'—H5'A | 109.5 |
O2—C1—O1 | 120.9 (2) | O2'—C1'—O1' | 121.1 (2) |
O2—C1—C17 | 122.7 (2) | O2'—C1'—C17' | 122.5 (2) |
O1—C1—C17 | 116.3 (2) | O1'—C1'—C17' | 116.3 (2) |
C3—C2—H2A | 109.5 | C3'—C2'—H2'A | 109.5 |
C3—C2—H2B | 109.5 | C3'—C2'—H2'B | 109.5 |
H2A—C2—H2B | 109.5 | H2'A—C2'—H2'B | 109.5 |
C3—C2—H2C | 109.5 | C3'—C2'—H2'C | 109.5 |
H2A—C2—H2C | 109.5 | H2'A—C2'—H2'C | 109.5 |
H2B—C2—H2C | 109.5 | H2'B—C2'—H2'C | 109.5 |
O1—C3—C2 | 109.9 (2) | O1'—C3'—C2' | 109.8 (2) |
O1—C3—C4 | 105.53 (19) | O1'—C3'—C4' | 105.24 (19) |
C2—C3—C4 | 113.1 (2) | C2'—C3'—C4' | 112.8 (2) |
O1—C3—H3B | 109.4 | O1'—C3'—H3'B | 109.6 |
C2—C3—H3B | 109.4 | C2'—C3'—H3'B | 109.6 |
C4—C3—H3B | 109.4 | C4'—C3'—H3'B | 109.6 |
C5—C4—C3 | 114.9 (2) | C3'—C4'—C5' | 114.6 (2) |
C5—C4—H4B | 108.5 | C3'—C4'—H4'B | 108.6 |
C3—C4—H4B | 108.5 | C5'—C4'—H4'B | 108.6 |
C5—C4—H4C | 108.5 | C3'—C4'—H4'C | 108.6 |
C3—C4—H4C | 108.5 | C5'—C4'—H4'C | 108.6 |
H4B—C4—H4C | 107.5 | H4'B—C4'—H4'C | 107.6 |
C4—C5—C6 | 114.8 (2) | C4'—C5'—C6' | 114.1 (2) |
C4—C5—H5B | 108.6 | C4'—C5'—H5'B | 108.7 |
C6—C5—H5B | 108.6 | C6'—C5'—H5'B | 108.7 |
C4—C5—H5C | 108.6 | C4'—C5'—H5'C | 108.7 |
C6—C5—H5C | 108.6 | C6'—C5'—H5'C | 108.7 |
H5B—C5—H5C | 107.5 | H5'B—C5'—H5'C | 107.6 |
C7—C6—C5 | 114.4 (2) | C7'—C6'—C5' | 114.9 (2) |
C7—C6—H6A | 108.7 | C7'—C6'—H6'A | 108.5 |
C5—C6—H6A | 108.7 | C5'—C6'—H6'A | 108.5 |
C7—C6—H6B | 108.7 | C7'—C6'—H6'B | 108.5 |
C5—C6—H6B | 108.7 | C5'—C6'—H6'B | 108.5 |
H6A—C6—H6B | 107.6 | H6'A—C6'—H6'B | 107.5 |
O3—C7—C6 | 110.1 (2) | O3'—C7'—C8' | 109.8 (2) |
O3—C7—C8 | 109.6 (2) | O3'—C7'—C6' | 110.6 (2) |
C6—C7—C8 | 114.5 (2) | C8'—C7'—C6' | 113.3 (2) |
O3—C7—H7A | 107.5 | O3'—C7'—H7'A | 107.6 |
C6—C7—H7A | 107.5 | C8'—C7'—H7'A | 107.6 |
C8—C7—H7A | 107.5 | C6'—C7'—H7'A | 107.6 |
C9—C8—C7 | 114.4 (2) | C7'—C8'—C9' | 113.6 (3) |
C9—C8—H8A | 108.7 | C7'—C8'—H8'A | 108.8 |
C7—C8—H8A | 108.7 | C9'—C8'—H8'A | 108.8 |
C9—C8—H8B | 108.7 | C7'—C8'—H8'B | 108.8 |
C7—C8—H8B | 108.7 | C9'—C8'—H8'B | 108.8 |
H8A—C8—H8B | 107.6 | H8'A—C8'—H8'B | 107.7 |
C10—C9—C8 | 114.9 (2) | C10'—C9'—C8' | 114.1 (2) |
C10—C9—H9A | 108.5 | C10'—C9'—H9'A | 108.7 |
C8—C9—H9A | 108.5 | C8'—C9'—H9'A | 108.7 |
C10—C9—H9B | 108.5 | C10'—C9'—H9'B | 108.7 |
C8—C9—H9B | 108.5 | C8'—C9'—H9'B | 108.7 |
H9A—C9—H9B | 107.5 | H9'A—C9'—H9'B | 107.6 |
C9—C10—C11 | 114.1 (2) | C11'—C10'—C9' | 114.4 (3) |
C9—C10—H10A | 108.7 | C11'—C10'—H10C | 108.7 |
C11—C10—H10A | 108.7 | C9'—C10'—H10C | 108.7 |
C9—C10—H10B | 108.7 | C11'—C10'—H10D | 108.7 |
C11—C10—H10B | 108.7 | C9'—C10'—H10D | 108.7 |
H10A—C10—H10B | 107.6 | H10C—C10'—H10D | 107.6 |
C12—C11—C10 | 112.7 (2) | C10'—C11'—C12' | 113.4 (2) |
C12—C11—H11A | 109.1 | C10'—C11'—H11C | 108.9 |
C10—C11—H11A | 109.1 | C12'—C11'—H11C | 108.9 |
C12—C11—H11B | 109.1 | C10'—C11'—H11D | 108.9 |
C10—C11—H11B | 109.1 | C12'—C11'—H11D | 108.9 |
H11A—C11—H11B | 107.8 | H11C—C11'—H11D | 107.7 |
C11—C12—C18 | 112.0 (2) | C18'—C12'—C11' | 111.6 (2) |
C11—C12—H12A | 109.2 | C18'—C12'—H12C | 109.3 |
C18—C12—H12A | 109.2 | C11'—C12'—H12C | 109.3 |
C11—C12—H12B | 109.2 | C18'—C12'—H12D | 109.3 |
C18—C12—H12B | 109.2 | C11'—C12'—H12D | 109.3 |
H12A—C12—H12B | 107.9 | H12C—C12'—H12D | 108.0 |
C18—C13—C14 | 122.0 (2) | C18'—C13'—C14' | 121.6 (2) |
C18—C13—H13A | 119.0 | C18'—C13'—H13B | 119.2 |
C14—C13—H13A | 119.0 | C14'—C13'—H13B | 119.2 |
O4—C14—C15 | 122.8 (2) | O4'—C14'—C15' | 122.5 (2) |
O4—C14—C13 | 116.8 (2) | O4'—C14'—C13' | 116.7 (2) |
C15—C14—C13 | 120.4 (2) | C15'—C14'—C13' | 120.8 (2) |
C14—C15—C16 | 119.3 (2) | C14'—C15'—C16' | 119.0 (2) |
C14—C15—H15A | 120.4 | C14'—C15'—H15B | 120.5 |
C16—C15—H15A | 120.4 | C16'—C15'—H15B | 120.5 |
O5—C16—C15 | 115.8 (2) | O5'—C16'—C15' | 115.6 (2) |
O5—C16—C17 | 123.2 (2) | O5'—C16'—C17' | 122.9 (2) |
C15—C16—C17 | 121.0 (2) | C15'—C16'—C17' | 121.5 (2) |
C18—C17—C16 | 118.8 (2) | C16'—C17'—C18' | 118.2 (2) |
C18—C17—C1 | 125.7 (2) | C16'—C17'—C1' | 116.0 (2) |
C16—C17—C1 | 115.6 (2) | C18'—C17'—C1' | 125.8 (2) |
C13—C18—C17 | 118.6 (2) | C13'—C18'—C17' | 118.8 (2) |
C13—C18—C12 | 116.4 (2) | C13'—C18'—C12' | 116.2 (2) |
C17—C18—C12 | 125.0 (2) | C17'—C18'—C12' | 124.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2 | 0.82 | 1.83 | 2.549 (3) | 146 |
O5′—H5′A···O2′ | 0.82 | 1.82 | 2.540 (3) | 146 |
O4—H4A···O3i | 0.83 (2) | 1.93 (3) | 2.745 (3) | 171 (3) |
O4′—H4′A···O3′ii | 0.82 (3) | 1.94 (3) | 2.740 (3) | 163 (4) |
O3—H3A···O4iii | 0.82 (3) | 2.29 (3) | 3.080 (3) | 162 (3) |
O3′—H3′A···O4′iii | 0.82 (3) | 2.27 (3) | 3.067 (3) | 165 (4) |
Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y+1, z; (iii) x, y−1, z. |
Experimental details
Crystal data | |
Chemical formula | C18H26O5 |
Mr | 322.39 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 5.0734 (11), 11.618 (2), 14.718 (3) |
α, β, γ (°) | 87.388 (13), 86.595 (15), 89.780 (15) |
V (Å3) | 865.0 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.43 × 0.22 × 0.10 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2001) |
Tmin, Tmax | 0.186, 0.350 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19642, 4264, 3421 |
Rint | 0.095 |
(sin θ/λ)max (Å−1) | 0.668 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.147, 0.95 |
No. of reflections | 4264 |
No. of parameters | 431 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.16 |
Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5A···O2 | 0.82 | 1.83 | 2.549 (3) | 146 |
O5'—H5'A···O2' | 0.82 | 1.82 | 2.540 (3) | 146 |
O4—H4A···O3i | 0.83 (2) | 1.93 (3) | 2.745 (3) | 171 (3) |
O4'—H4'A···O3'ii | 0.82 (3) | 1.94 (3) | 2.740 (3) | 163 (4) |
O3—H3A···O4iii | 0.82 (3) | 2.29 (3) | 3.080 (3) | 162 (3) |
O3'—H3'A···O4'iii | 0.82 (3) | 2.27 (3) | 3.067 (3) | 165 (4) |
Symmetry codes: (i) x+1, y+1, z; (ii) x−1, y+1, z; (iii) x, y−1, z. |
References
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
α-Zearalanol (α-ZAL, generic name Zeranol) is a resorcylic acid lactone (RAL) with estrogenic and anabolic activity. α-ZAL can be obtained chemically by reduction of zearalenone (ZEN) (Urry et al. 1966), a mycotoxin produced by a variety of Fusarium fungi and well known crop contaminant. α-ZAL also occurs naturally as a metabolite of zearalanone (ZAN), another ZEN derivative (Baldwin et al., 1983). Crystal structures of ZEN and ZEN derivatives have been elucidated by Panneerselvam et al. (1996), Gelo-Pujić et al. (1994), Zhao et al. (2008), Köppen et al. (2012) and Drzymala et al. (2012).
ZEN-related structures have a more or less pronounced hormonal activity. Particularly α-ZAL proved to be an effective anabolic hormone. Marketed under the trade name Ralgro, it is widely used as a growth promoter in cattle. In contrast to the U.S.A., Canada and several other countries, α-Zearalanol was banned by the EU in 1985 (Wang & Wang, 2007) resulting in a series of legal issues between the US and the EU. Due to its growth promoting effects α-ZAL also belongs to the list of substances prohibited in sports as classified by the World Anti-Doping Agency.
The compound has a macrocyclic structure and crystallizes in the triclinic space group P1. The molecular structure of the compound and the atom-labeling scheme are shown in Fig 1. The absolute configuration could not be defined confidently based on the single-crystal diffraction data. The isomeric purity of the title compound was confirmed by 1H-NMR, HPLC-DAD and –MS/MS data. Fig. 4 shows the difference in conformation between the known β-Zearalanol (Gelo-Pujić et al., 1994) and the title compound. Every molecule in the asymmetric unit builds an infinite chain with the help of hydrogen bonds of the hydroxyl groups. The two chains in relation to the unit cell are depicted in Fig. 2. The analysis of polymeric structures shows two infinite one dimensional chains with the base vectors of [1 1 0] and [1 - 1 0], Fig 3.