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Volume 68 
Part 11 
Page o3071  
November 2012  

Received 3 September 2012
Accepted 1 October 2012
Online 6 October 2012

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Key indicators
Single-crystal X-ray study
T = 296 K
Mean [sigma](C-C) = 0.004 Å
R = 0.059
wR = 0.147
Data-to-parameter ratio = 9.9
Details
Open access

(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 Emmerlinga and Matthias Kocha

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 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].

Related literature

For the chemical preparation of [alpha]-zearalanol, see: Urry et al. (1966[Urry, W. H., Wehrmeister, H. L., Hodge, E. B. & Hidy, P. H. (1966). Tetrahedron Lett. 7, 3109-3114.]). For its natural occurrence as a metabolite, see: Baldwin et al. (1983[Baldwin, R. S., Williams, R. D. & Terry, M. K. (1983). Regul. Toxicol. Pharmacol. 3, 9-25.]) and for its use as an animal growth promoter, see: Wang & Wang (2007[Wang, S. & Wang, X. H. (2007). Food Addit. Contam. 24, 573-582.]). For the crystal structures of related derivatives, see: Panneerselvam et al. (1996[Panneerselvam, K., Rudiño-Piñera, E. & Soriano-García, M. (1996). Acta Cryst. C52, 3095-3097.]); Gelo-Pujic et al. (1994[Gelo-Pujic, M., Antolic, S., Kojic-Prodic, B. & Sunjic, V. (1994). Tetrahedron, 50, 13753-13764.]); Zhao et al. (2008[Zhao, L.-L., Gai, Y., Kobayashi, H., Hu, C.-Q. & Zhang, H.-P. (2008). Acta Cryst. E64, o999.]); Köppen et al. (2012[Köppen, R., Riedel, J., Emmerling, F. & Koch, M. (2012). Acta Cryst. E68, o832.]); Drzymala et al. (2012[Drzymala, S., Kraus, W., Emmerling, F. & Koch, M. (2012). Acta Cryst. E68, o1577.]).

[Scheme 1]

Experimental

Crystal data

  • C18H26O5

  • Mr = 322.39

  • Triclinic, P 1

  • a = 5.0734 (11) Å

  • b = 11.618 (2) Å

  • c = 14.718 (3) Å

  • [alpha] = 87.388 (13)°

  • [beta] = 86.595 (15)°

  • [gamma] = 89.780 (15)°

  • V = 865.0 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.186, Tmax = 0.350

  • 19642 measured reflections

  • 4264 independent reflections

  • 3421 reflections with I > 2[sigma](I)

  • Rint = 0.095
Refinement

  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]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[Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2595 ).

References

Baldwin, R. S., Williams, R. D. & Terry, M. K. (1983). Regul. Toxicol. Pharmacol. 3, 9-25.  [CrossRef] [ChemPort] [PubMed]
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.  [CSD] [CrossRef] [details]
Gelo-Pujic, M., Antolic, S., Kojic-Prodic, B. & Sunjic, V. (1994). Tetrahedron, 50, 13753-13764.  [CrossRef] [ISI]
Köppen, R., Riedel, J., Emmerling, F. & Koch, M. (2012). Acta Cryst. E68, o832.  [CSD] [CrossRef] [details]
Panneerselvam, K., Rudiño-Piñera, E. & Soriano-García, M. (1996). Acta Cryst. C52, 3095-3097.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Urry, W. H., Wehrmeister, H. L., Hodge, E. B. & Hidy, P. H. (1966). Tetrahedron Lett. 7, 3109-3114.  [CrossRef]
Wang, S. & Wang, X. H. (2007). Food Addit. Contam. 24, 573-582.  [CrossRef] [PubMed] [ChemPort]
Zhao, L.-L., Gai, Y., Kobayashi, H., Hu, C.-Q. & Zhang, H.-P. (2008). Acta Cryst. E64, o999.  [CSD] [CrossRef] [details]

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

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