supplementary materials


fj2595 scheme

Acta Cryst. (2012). E68, o3071    [ doi:10.1107/S1600536812041141 ]

(3S,7R)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12-decahydro-1H-2-benzoxacyclotetradecin-1-one.

S. Drzymala, W. Kraus, F. Emmerling and M. Koch

Abstract top

The asymmetric unit of the title compound, C18H26O5, which is known as [alpha]-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].

Comment top

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.

Related literature top

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 top

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.

Refinement top

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 anomalous dispersion effects 3785 Friedel pairs were merged. The absolute configuration has not been determined by anomalous-dispersion effects in diffraction measurements of the crystal. The enantiomer has been assigned by reference to an unchanging chiral centre in the synthetic procedure.

Computing details top

Data collection: APEX2 (Bruker, 2001); cell refinement: 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).

Figures top
[Figure 1] Fig. 1. : ORTEP representation of the title compound with atomic labeling shown with 30% probability displacement ellipsoids.
[Figure 2] 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.
[Figure 3] 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.
[Figure 4] Fig. 4. : The difference in conformation between the known β-Zearalanol (yellow, Gelo-Pujić et al., 1994) and the title compound.
(3S,7R)-7,14,16-Trihydroxy-3-methyl-3,4,5,6,7,8,9,10,11,12- decahydro-1H-2-benzoxacyclotetradecin-1-one. top
Crystal data top
C18H26O5Z = 2
Mr = 322.39F(000) = 348
Triclinic, P1Dx = 1.238 Mg m3
a = 5.0734 (11) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.618 (2) ÅCell parameters from 6563 reflections
c = 14.718 (3) Åθ = 2.3–26.4°
α = 87.388 (13)°µ = 0.09 mm1
β = 86.595 (15)°T = 296 K
γ = 89.780 (15)°Block, colourless
V = 865.0 (3) Å30.43 × 0.22 × 0.10 mm
Data collection top
Bruker APEXII CCD
diffractometer
4264 independent reflections
Radiation source: fine-focus sealed tube3421 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.095
φ and ω scansθmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 66
Tmin = 0.186, Tmax = 0.350k = 1515
19642 measured reflectionsl = 1919
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.059Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H 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 parametersΔρmax = 0.24 e Å3
7 restraintsΔρmin = 0.16 e Å3
Crystal data top
C18H26O5γ = 89.780 (15)°
Mr = 322.39V = 865.0 (3) Å3
Triclinic, P1Z = 2
a = 5.0734 (11) ÅMo Kα radiation
b = 11.618 (2) ŵ = 0.09 mm1
c = 14.718 (3) ÅT = 296 K
α = 87.388 (13)°0.43 × 0.22 × 0.10 mm
β = 86.595 (15)°
Data collection top
Bruker APEXII CCD
diffractometer
4264 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
3421 reflections with I > 2σ(I)
Tmin = 0.186, Tmax = 0.350Rint = 0.095
19642 measured reflectionsθmax = 28.3°
Refinement top
R[F2 > 2σ(F2)] = 0.059H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.147Δρmax = 0.24 e Å3
S = 0.95Δρmin = 0.16 e Å3
4264 reflectionsAbsolute structure: ?
431 parametersFlack parameter: ?
7 restraintsRogers parameter: ?
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
O10.1448 (4)0.89233 (14)0.65863 (11)0.0465 (4)
O20.0413 (4)0.99572 (16)0.76207 (12)0.0555 (5)
O30.3004 (5)0.45828 (17)0.45181 (16)0.0618 (6)
O40.2440 (5)1.34395 (16)0.41989 (13)0.0570 (5)
O50.3693 (4)1.15285 (17)0.70652 (13)0.0578 (5)
H5A0.30151.10380.74230.087*
C10.0231 (5)0.9872 (2)0.68358 (16)0.0409 (5)
C20.4309 (7)0.8317 (3)0.7915 (2)0.0683 (8)
H2A0.39010.90000.82220.102*
H2B0.46940.76980.83560.102*
H2C0.58170.84590.75610.102*
C30.1985 (5)0.7995 (2)0.72962 (16)0.0435 (6)
H3B0.04290.78820.76540.052*
C40.2456 (5)0.6918 (2)0.67829 (18)0.0469 (6)
H4B0.31920.63290.72110.056*
H4C0.37630.70930.63410.056*
C50.0035 (6)0.6437 (2)0.6292 (2)0.0526 (7)
H5B0.12270.62150.67380.063*
H5C0.07670.70420.58930.063*
C60.0549 (7)0.5390 (2)0.5722 (2)0.0580 (7)
H6A0.11350.50810.55000.070*
H6B0.14240.47970.61150.070*
C70.2229 (6)0.5653 (2)0.49103 (19)0.0493 (6)
H7A0.38460.60330.51400.059*
C80.0915 (6)0.6456 (2)0.41628 (19)0.0535 (7)
H8A0.03510.69370.44350.064*
H8B0.00530.59910.37250.064*
C90.2828 (6)0.7229 (2)0.36581 (18)0.0563 (7)
H9A0.19330.75320.30970.068*
H9B0.42940.67630.34930.068*
C100.3925 (6)0.8235 (2)0.41891 (19)0.0482 (6)
H10A0.48310.79350.47490.058*
H10B0.52180.86370.38330.058*
C110.1827 (5)0.9100 (2)0.44291 (17)0.0444 (6)
H11A0.05300.87010.47870.053*
H11B0.09250.94080.38710.053*
C120.2995 (5)1.0093 (2)0.49636 (17)0.0411 (5)
H12A0.40170.97850.54970.049*
H12B0.41821.05320.45870.049*
C130.0089 (5)1.1798 (2)0.46580 (17)0.0438 (6)
H13A0.09181.18910.41130.053*
C140.1884 (5)1.2568 (2)0.48410 (17)0.0437 (6)
C150.3129 (6)1.2462 (2)0.56527 (18)0.0457 (6)
H15A0.44481.29770.57750.055*
C160.2384 (5)1.1575 (2)0.62849 (16)0.0415 (5)
C170.0383 (5)1.07732 (19)0.61033 (16)0.0372 (5)
C180.0857 (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'A0.10340.59410.85470.091*
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'A0.80520.40140.78070.109*
H2'B0.89040.27290.76860.109*
H2'C0.98970.34030.84980.109*
C3'0.6061 (5)0.2899 (2)0.87071 (17)0.0436 (6)
H3'B0.45480.28320.83290.052*
C4'0.6511 (6)0.1755 (2)0.92215 (19)0.0484 (6)
H4'B0.77330.18780.96900.058*
H4'C0.73380.12240.88010.058*
C5'0.4010 (6)0.1196 (2)0.96673 (18)0.0497 (6)
H5'B0.28530.10090.91940.060*
H5'C0.30990.17501.00470.060*
C6'0.4513 (6)0.0096 (2)1.02532 (19)0.0548 (7)
H6'A0.28270.02631.04320.066*
H6'B0.55240.04370.98820.066*
C7'0.5984 (6)0.0283 (2)1.11146 (18)0.0472 (6)
H7'A0.75750.07331.09330.057*
C8'0.4374 (6)0.0953 (2)1.18242 (19)0.0511 (6)
H8'A0.33080.04151.22100.061*
H8'B0.31830.14711.15140.061*
C9'0.6079 (7)0.1660 (2)1.24287 (19)0.0594 (8)
H9'A0.49820.19051.29470.071*
H9'B0.74550.11661.26600.071*
C10'0.7366 (6)0.2724 (2)1.1937 (2)0.0537 (7)
H10C0.85320.30731.23450.064*
H10D0.84400.24791.14140.064*
C11'0.5409 (6)0.3635 (2)1.16147 (18)0.0491 (6)
H11C0.43880.39091.21400.059*
H11D0.41940.32811.12270.059*
C12'0.6742 (5)0.4672 (2)1.10867 (18)0.0440 (6)
H12C0.79030.50501.14800.053*
H12D0.78100.44011.05710.053*
C13'0.3928 (6)0.6373 (2)1.13423 (18)0.0456 (6)
H13B0.47040.64011.18980.055*
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)
H15B0.05230.76901.01800.054*
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)
H4A0.388 (4)1.371 (3)0.431 (2)0.073 (11)*
H3'A0.543 (5)0.113 (4)1.169 (3)0.108 (17)*
H3A0.175 (5)0.418 (3)0.436 (3)0.087 (14)*
H4'A0.005 (5)0.823 (4)1.163 (4)0.13 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0625 (12)0.0364 (9)0.0408 (9)0.0108 (8)0.0077 (8)0.0041 (7)
O20.0760 (13)0.0506 (10)0.0408 (9)0.0087 (10)0.0120 (9)0.0022 (8)
O30.0717 (16)0.0379 (11)0.0762 (14)0.0139 (11)0.0031 (12)0.0090 (9)
O40.0772 (15)0.0375 (10)0.0557 (11)0.0172 (10)0.0011 (11)0.0022 (8)
O50.0702 (13)0.0535 (11)0.0519 (11)0.0147 (10)0.0194 (10)0.0050 (9)
C10.0458 (14)0.0372 (12)0.0393 (13)0.0009 (10)0.0025 (10)0.0048 (9)
C20.066 (2)0.0638 (19)0.072 (2)0.0032 (16)0.0199 (16)0.0031 (15)
C30.0473 (14)0.0422 (13)0.0400 (12)0.0025 (11)0.0010 (10)0.0090 (10)
C40.0490 (15)0.0413 (14)0.0494 (14)0.0106 (11)0.0020 (11)0.0078 (11)
C50.0513 (16)0.0489 (15)0.0584 (16)0.0009 (13)0.0098 (13)0.0034 (12)
C60.072 (2)0.0400 (14)0.0628 (17)0.0007 (13)0.0070 (15)0.0040 (12)
C70.0560 (16)0.0319 (12)0.0593 (16)0.0116 (11)0.0059 (13)0.0059 (11)
C80.0623 (18)0.0402 (14)0.0568 (16)0.0132 (13)0.0130 (14)0.0098 (12)
C90.078 (2)0.0482 (15)0.0433 (13)0.0210 (14)0.0054 (13)0.0057 (11)
C100.0565 (16)0.0425 (13)0.0466 (13)0.0088 (12)0.0128 (12)0.0004 (10)
C110.0509 (15)0.0368 (12)0.0456 (13)0.0098 (11)0.0031 (11)0.0029 (10)
C120.0397 (13)0.0377 (12)0.0462 (13)0.0041 (10)0.0068 (10)0.0001 (10)
C130.0559 (16)0.0344 (12)0.0420 (13)0.0015 (11)0.0082 (11)0.0033 (10)
C140.0554 (15)0.0291 (11)0.0461 (13)0.0034 (11)0.0019 (11)0.0035 (10)
C150.0515 (14)0.0356 (12)0.0506 (14)0.0083 (11)0.0005 (11)0.0105 (10)
C160.0462 (14)0.0379 (13)0.0413 (13)0.0012 (11)0.0031 (11)0.0091 (10)
C170.0438 (13)0.0297 (11)0.0384 (11)0.0005 (10)0.0001 (10)0.0067 (9)
C180.0377 (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)
Geometric parameters (Å, º) top
O1—C11.341 (3)O1'—C1'1.331 (3)
O1—C31.482 (3)O1'—C3'1.483 (3)
O2—C11.227 (3)O2'—C1'1.232 (3)
O3—C71.460 (3)O3'—C7'1.456 (3)
O3—H3A0.818 (10)O3'—H3'A0.821 (10)
O4—C141.372 (3)O4'—C14'1.370 (3)
O4—H4A0.826 (10)O4'—H4'A0.821 (10)
O5—C161.359 (3)O5'—C16'1.365 (3)
O5—H5A0.8200O5'—H5'A0.8200
C1—C171.489 (3)C1'—C17'1.476 (3)
C2—C31.503 (4)C2'—C3'1.504 (4)
C2—H2A0.9600C2'—H2'A0.9600
C2—H2B0.9600C2'—H2'B0.9600
C2—H2C0.9600C2'—H2'C0.9600
C3—C41.517 (4)C3'—C4'1.523 (4)
C3—H3B0.9800C3'—H3'B0.9800
C4—C51.507 (4)C4'—C5'1.527 (4)
C4—H4B0.9700C4'—H4'B0.9700
C4—H4C0.9700C4'—H4'C0.9700
C5—C61.540 (4)C5'—C6'1.538 (4)
C5—H5B0.9700C5'—H5'B0.9700
C5—H5C0.9700C5'—H5'C0.9700
C6—C71.527 (4)C6'—C7'1.533 (4)
C6—H6A0.9700C6'—H6'A0.9700
C6—H6B0.9700C6'—H6'B0.9700
C7—C81.532 (4)C7'—C8'1.527 (4)
C7—H7A0.9800C7'—H7'A0.9800
C8—C91.523 (5)C8'—C9'1.542 (4)
C8—H8A0.9700C8'—H8'A0.9700
C8—H8B0.9700C8'—H8'B0.9700
C9—C101.520 (4)C9'—C10'1.532 (4)
C9—H9A0.9700C9'—H9'A0.9700
C9—H9B0.9700C9'—H9'B0.9700
C10—C111.534 (3)C10'—C11'1.528 (4)
C10—H10A0.9700C10'—H10C0.9700
C10—H10B0.9700C10'—H10D0.9700
C11—C121.524 (3)C11'—C12'1.540 (4)
C11—H11A0.9700C11'—H11C0.9700
C11—H11B0.9700C11'—H11D0.9700
C12—C181.531 (3)C12'—C18'1.520 (3)
C12—H12A0.9700C12'—H12C0.9700
C12—H12B0.9700C12'—H12D0.9700
C13—C181.388 (3)C13'—C18'1.381 (3)
C13—C141.391 (4)C13'—C14'1.392 (4)
C13—H13A0.9300C13'—H13B0.9300
C14—C151.385 (4)C14'—C15'1.379 (4)
C15—C161.394 (3)C15'—C16'1.387 (4)
C15—H15A0.9300C15'—H15B0.9300
C16—C171.425 (3)C16'—C17'1.421 (3)
C17—C181.419 (3)C17'—C18'1.428 (3)
C1—O1—C3117.26 (18)C1'—O1'—C3'116.96 (18)
C7—O3—H3A113 (3)C7'—O3'—H3'A103 (3)
C14—O4—H4A106 (3)C14'—O4'—H4'A104 (4)
C16—O5—H5A109.5C16'—O5'—H5'A109.5
O2—C1—O1120.9 (2)O2'—C1'—O1'121.1 (2)
O2—C1—C17122.7 (2)O2'—C1'—C17'122.5 (2)
O1—C1—C17116.3 (2)O1'—C1'—C17'116.3 (2)
C3—C2—H2A109.5C3'—C2'—H2'A109.5
C3—C2—H2B109.5C3'—C2'—H2'B109.5
H2A—C2—H2B109.5H2'A—C2'—H2'B109.5
C3—C2—H2C109.5C3'—C2'—H2'C109.5
H2A—C2—H2C109.5H2'A—C2'—H2'C109.5
H2B—C2—H2C109.5H2'B—C2'—H2'C109.5
O1—C3—C2109.9 (2)O1'—C3'—C2'109.8 (2)
O1—C3—C4105.53 (19)O1'—C3'—C4'105.24 (19)
C2—C3—C4113.1 (2)C2'—C3'—C4'112.8 (2)
O1—C3—H3B109.4O1'—C3'—H3'B109.6
C2—C3—H3B109.4C2'—C3'—H3'B109.6
C4—C3—H3B109.4C4'—C3'—H3'B109.6
C5—C4—C3114.9 (2)C3'—C4'—C5'114.6 (2)
C5—C4—H4B108.5C3'—C4'—H4'B108.6
C3—C4—H4B108.5C5'—C4'—H4'B108.6
C5—C4—H4C108.5C3'—C4'—H4'C108.6
C3—C4—H4C108.5C5'—C4'—H4'C108.6
H4B—C4—H4C107.5H4'B—C4'—H4'C107.6
C4—C5—C6114.8 (2)C4'—C5'—C6'114.1 (2)
C4—C5—H5B108.6C4'—C5'—H5'B108.7
C6—C5—H5B108.6C6'—C5'—H5'B108.7
C4—C5—H5C108.6C4'—C5'—H5'C108.7
C6—C5—H5C108.6C6'—C5'—H5'C108.7
H5B—C5—H5C107.5H5'B—C5'—H5'C107.6
C7—C6—C5114.4 (2)C7'—C6'—C5'114.9 (2)
C7—C6—H6A108.7C7'—C6'—H6'A108.5
C5—C6—H6A108.7C5'—C6'—H6'A108.5
C7—C6—H6B108.7C7'—C6'—H6'B108.5
C5—C6—H6B108.7C5'—C6'—H6'B108.5
H6A—C6—H6B107.6H6'A—C6'—H6'B107.5
O3—C7—C6110.1 (2)O3'—C7'—C8'109.8 (2)
O3—C7—C8109.6 (2)O3'—C7'—C6'110.6 (2)
C6—C7—C8114.5 (2)C8'—C7'—C6'113.3 (2)
O3—C7—H7A107.5O3'—C7'—H7'A107.6
C6—C7—H7A107.5C8'—C7'—H7'A107.6
C8—C7—H7A107.5C6'—C7'—H7'A107.6
C9—C8—C7114.4 (2)C7'—C8'—C9'113.6 (3)
C9—C8—H8A108.7C7'—C8'—H8'A108.8
C7—C8—H8A108.7C9'—C8'—H8'A108.8
C9—C8—H8B108.7C7'—C8'—H8'B108.8
C7—C8—H8B108.7C9'—C8'—H8'B108.8
H8A—C8—H8B107.6H8'A—C8'—H8'B107.7
C10—C9—C8114.9 (2)C10'—C9'—C8'114.1 (2)
C10—C9—H9A108.5C10'—C9'—H9'A108.7
C8—C9—H9A108.5C8'—C9'—H9'A108.7
C10—C9—H9B108.5C10'—C9'—H9'B108.7
C8—C9—H9B108.5C8'—C9'—H9'B108.7
H9A—C9—H9B107.5H9'A—C9'—H9'B107.6
C9—C10—C11114.1 (2)C11'—C10'—C9'114.4 (3)
C9—C10—H10A108.7C11'—C10'—H10C108.7
C11—C10—H10A108.7C9'—C10'—H10C108.7
C9—C10—H10B108.7C11'—C10'—H10D108.7
C11—C10—H10B108.7C9'—C10'—H10D108.7
H10A—C10—H10B107.6H10C—C10'—H10D107.6
C12—C11—C10112.7 (2)C10'—C11'—C12'113.4 (2)
C12—C11—H11A109.1C10'—C11'—H11C108.9
C10—C11—H11A109.1C12'—C11'—H11C108.9
C12—C11—H11B109.1C10'—C11'—H11D108.9
C10—C11—H11B109.1C12'—C11'—H11D108.9
H11A—C11—H11B107.8H11C—C11'—H11D107.7
C11—C12—C18112.0 (2)C18'—C12'—C11'111.6 (2)
C11—C12—H12A109.2C18'—C12'—H12C109.3
C18—C12—H12A109.2C11'—C12'—H12C109.3
C11—C12—H12B109.2C18'—C12'—H12D109.3
C18—C12—H12B109.2C11'—C12'—H12D109.3
H12A—C12—H12B107.9H12C—C12'—H12D108.0
C18—C13—C14122.0 (2)C18'—C13'—C14'121.6 (2)
C18—C13—H13A119.0C18'—C13'—H13B119.2
C14—C13—H13A119.0C14'—C13'—H13B119.2
O4—C14—C15122.8 (2)O4'—C14'—C15'122.5 (2)
O4—C14—C13116.8 (2)O4'—C14'—C13'116.7 (2)
C15—C14—C13120.4 (2)C15'—C14'—C13'120.8 (2)
C14—C15—C16119.3 (2)C14'—C15'—C16'119.0 (2)
C14—C15—H15A120.4C14'—C15'—H15B120.5
C16—C15—H15A120.4C16'—C15'—H15B120.5
O5—C16—C15115.8 (2)O5'—C16'—C15'115.6 (2)
O5—C16—C17123.2 (2)O5'—C16'—C17'122.9 (2)
C15—C16—C17121.0 (2)C15'—C16'—C17'121.5 (2)
C18—C17—C16118.8 (2)C16'—C17'—C18'118.2 (2)
C18—C17—C1125.7 (2)C16'—C17'—C1'116.0 (2)
C16—C17—C1115.6 (2)C18'—C17'—C1'125.8 (2)
C13—C18—C17118.6 (2)C13'—C18'—C17'118.8 (2)
C13—C18—C12116.4 (2)C13'—C18'—C12'116.2 (2)
C17—C18—C12125.0 (2)C17'—C18'—C12'124.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O20.821.832.549 (3)146
O5—H5A···O20.821.822.540 (3)146
O4—H4A···O3i0.83 (2)1.93 (3)2.745 (3)171 (3)
O4—H4A···O3ii0.82 (3)1.94 (3)2.740 (3)163 (4)
O3—H3A···O4iii0.82 (3)2.29 (3)3.080 (3)162 (3)
O3—H3A···O4iii0.82 (3)2.27 (3)3.067 (3)165 (4)
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y+1, z; (iii) x, y1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O5—H5A···O20.821.832.549 (3)146
O5'—H5'A···O2'0.821.822.540 (3)146
O4—H4A···O3i0.83 (2)1.93 (3)2.745 (3)171 (3)
O4'—H4'A···O3'ii0.82 (3)1.94 (3)2.740 (3)163 (4)
O3—H3A···O4iii0.82 (3)2.29 (3)3.080 (3)162 (3)
O3'—H3'A···O4'iii0.82 (3)2.27 (3)3.067 (3)165 (4)
Symmetry codes: (i) x+1, y+1, z; (ii) x1, y+1, z; (iii) x, y1, z.
references
References top

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Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Drzymala, S., Kraus, W., Emmerling, F. & Koch, M. (2012). Acta Cryst. E68, o1577.

Gelo-Pujić, M., Antolić, S., Kojić-Prodić, B. & Šunjić, V. (1994). Tetrahedron, 50, 13753–13764.

Köppen, R., Riedel, J., Emmerling, F. & Koch, M. (2012). Acta Cryst. E68, o832.

Panneerselvam, K., Rudiño-Piñera, E. & Soriano-García, M. (1996). Acta Cryst. C52, 3095–3097.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Urry, W. H., Wehrmeister, H. L., Hodge, E. B. & Hidy, P. H. (1966). Tetrahedron Lett. 7, 3109–3114.

Wang, S. & Wang, X. H. (2007). Food Addit. Contam. 24, 573–582.

Zhao, L.-L., Gai, Y., Kobayashi, H., Hu, C.-Q. & Zhang, H.-P. (2008). Acta Cryst. E64, o999.