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

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

doi:10.1107/S1600536812041141

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3071

doi:10.1107/S1600536812041141

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

Sarah Drzymala,^a ^* Werner Kraus,^a Franziska Emmerling ^a and Matthias Koch ^a

^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

(Received 3 September 2012; accepted 1 October 2012; online 6 October 2012)

The asymmetric unit of the title compound, C₁₈H₂₆O₅, 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].

Related 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

C₁₈H₂₆O₅
M_r = 322.39
Triclinic, P 1
a = 5.0734 (11) Å
b = 11.618 (2) Å
c = 14.718 (3) Å
α = 87.388 (13)°
β = 86.595 (15)°
γ = 89.780 (15)°
V = 865.0 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 296 K
0.43 × 0.22 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.186, T_max = 0.350
19642 measured reflections
4264 independent reflections
3421 reflections with I > 2σ(I)
R_int = 0.095

Refinement

R[F² > 2σ(F²)] = 0.059
wR(F²) = 0.147
S = 0.95
4264 reflections
431 parameters
7 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.24 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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.

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

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536812041141/fj2595sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041141/fj2595Isup2.hkl

checkCIF report

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.

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

	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.

(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

C₁₈H₂₆O₅	Z = 2
M_r = 322.39	F(000) = 348
Triclinic, P1	D_x = 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

Data collection top

Bruker APEXII CCD diffractometer	4264 independent reflections
Radiation source: fine-focus sealed tube	3421 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.095
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −6→6
T_min = 0.186, T_max = 0.350	k = −15→15
19642 measured reflections	l = −19→19

Refinement top

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(F_o²) + (0.0803P)²] where P = (F_o² + 2F_c²)/3
4264 reflections	(Δ/σ)_max < 0.001
431 parameters	Δρ_max = 0.24 e Å⁻³
7 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₈H₂₆O₅	γ = 89.780 (15)°
M_r = 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)°

Data collection top

Bruker APEXII CCD diffractometer	4264 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3421 reflections with I > 2σ(I)
T_min = 0.186, T_max = 0.350	R_int = 0.095
19642 measured reflections

Refinement top

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	Δρ_max = 0.24 e Å⁻³
4264 reflections	Δρ_min = −0.16 e Å⁻³
431 parameters

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.186, 0.350
No. of measured, independent and observed [I > 2σ(I)] reflections	19642, 4264, 3421
R_int	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
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.16

Computer programs: APEX2 (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

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

Baldwin, R. S., Williams, R. D. & Terry, M. K. (1983). Regul. Toxicol. Pharmacol. 3, 9–25. CrossRef CAS PubMed Google Scholar
Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Drzymala, S., Kraus, W., Emmerling, F. & Koch, M. (2012). Acta Cryst. E68, o1577. CSD CrossRef IUCr Journals Google Scholar
Gelo-Pujić, M., Antolić, S., Kojić-Prodić, B. & Šunjić, V. (1994). Tetrahedron, 50, 13753–13764. CSD CrossRef Web of Science Google Scholar
Köppen, R., Riedel, J., Emmerling, F. & Koch, M. (2012). Acta Cryst. E68, o832. CSD CrossRef IUCr Journals Google Scholar
Panneerselvam, K., Rudiño-Piñera, E. & Soriano-García, M. (1996). Acta Cryst. C52, 3095–3097. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Urry, W. H., Wehrmeister, H. L., Hodge, E. B. & Hidy, P. H. (1966). Tetrahedron Lett. 7, 3109–3114. CrossRef Google Scholar
Wang, S. & Wang, X. H. (2007). Food Addit. Contam. 24, 573–582. Web of Science CrossRef PubMed CAS Google Scholar
Zhao, L.-L., Gai, Y., Kobayashi, H., Hu, C.-Q. & Zhang, H.-P. (2008). Acta Cryst. E64, o999. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 68| Part 11| November 2012| Page o3071

doi:10.1107/S1600536812041141

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

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.