(3S)-14,16-Dihy­droxy-3-methyl-3,4,5,6,9,10,11,12-octa­hydro-1H-2-benzoxacyclo­tetra­decine-1,7(8H)-dione (zearalanone) monohydrate

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

doi:10.1107/S1600536812018168

Volume 68
Part 5
Page o1577
May 2012

Received 11 April 2012
Accepted 23 April 2012
Online 28 April 2012

Key indicators
Single-crystal X-ray study
T = 296 K
Mean (C-C) = 0.003 Å
R = 0.051
wR = 0.134
Data-to-parameter ratio = 20.6
Details

(3S)-14,16-Dihydroxy-3-methyl-3,4,5,6,9,10,11,12-octahydro-1H-2-benzoxacyclotetradecine-1,7(8H)-dione (zearalanone) monohydrate

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

The absolute configuration of the title compound, C₁₈H₂₄O₅·H₂O, was not been determined by anomalous-dispersion effects, but has been assigned by reference to an unchanging chiral centre in the synthetic procedure. Intramolecular O-HO hydrogen bonds stabilize the molecular conformation. In the crystal, O-HO hydrogen bonds link the main molecules and the water molecules, forming an infinite three-dimensional network.

Related literature

For the preparation of zearalanone from natural zearalenone, see: Urry et al. (1966). For the crystal structures of zearalenone and its derivatives, see: Panneerselvam et al. (1996); Gelo-Pujic et al. (1994); Zhao et al. (2008). For the estrogenic and anabolic effects of zearalenone and its derivatives, see: Mirocha et al. (1968). For the exploitation of zearalanone as an internal standard, see: Berthiller et al. (2005); Maragou et al. (2008); Ren et al. (2007); Shin et al. (2009).

Experimental

Crystal data

C₁₈H₂₄O₅·H₂O
M_r = 338.39
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.2727 (11) Å
b = 24.579 (3) Å
c = 9.3703 (14) Å
V = 1905.3 (5) Å³
Z = 4
Mo K radiation
= 0.09 mm^-1
T = 296 K
0.45 × 0.25 × 0.1 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001) T_min = 0.151, T_max = 0.477
20473 measured reflections
4626 independent reflections
2870 reflections with I > 2(I)
R_int = 0.109

Refinement

R[F² > 2(F²)] = 0.051
wR(F²) = 0.134
S = 0.90
4626 reflections
225 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
_max = 0.18 e Å^-3
_min = -0.15 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
O4-H4AO6	0.82	1.87	2.693 (2)	176
O5-H5AO2	0.82	1.86	2.581 (2)	147
O6-H6CO3ⁱ	0.96 (2)	1.85 (2)	2.810 (3)	178 (3)
O6-H6DO5ⁱⁱ	0.96 (2)	1.95 (2)	2.887 (2)	164 (2)
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+2, z+{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, -z+1]$ .

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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2544 ).

Acknowledgements

The authors thank Dr Robert Köppen from the Federal Institute for Materials Research and Testing (BAM) for his assistance in obtaining zearalanone crystals.

References

Berthiller, F., Schuhmacher, R., Buttinger, G. & Krska, R. (2005). J. Chromatogr. A, 1062, 209-216.
Bruker (2001). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Gelo-Pujic, M., Antolic, S., Kojic-Prodic, B. & Sunjic, V. (1994). Tetrahedron, 50, 13753-13764.
Maragou, N. C., Rosenberg, E., Thomaidis, N. S. & Koupparis, M. A. (2008). J. Chromatogr. A, 1202, 47-57.
Mirocha, C. J., Christensen, C. M. & Nelson, G. H. (1968). Cancer Res. 28, 2319-2322.
Panneerselvam, K., Rudiño-Piñera, E. & Soriano-García, M. (1996). Acta Cryst. C52, 3095-3097.
Ren, Y., Zhang, Y., Shao, S., Cai, Z., Feng, L., Pan, H. & Wang, Z. (2007). J. Chromatogr. A, 1143, 48-64.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Shin, B. S., Hong, S. H., Hwang, S. W., Kim, H. J., Lee, J. B., Yoon, H. S., Kim do, J. & Yoo, S. D. (2009). Biomed. Chromatogr. 23, 1014-1021.
Urry, W. H., Wehrmeister, H. L., Hodge, E. B. & Hidy, P. H. (1966). Tetrahedron Lett. 7, 3109-3114.
Zhao, L.-L., Gai, Y., Kobayashi, H., Hu, C.-Q. & Zhang, H.-P. (2008). Acta Cryst. E64, o999.

organic compounds