(3S)-14,16-Dihy-droxy-3-methyl-3,4,5,6,9,10,11,12-octa-hydro-1H-2-benzoxacyclo-tetra-decine-1,7(8H)-dione (zearalanone) monohydrate.

The absolute configuration of the title compound, C(18)H(24)O(5)·H(2)O, was not been determined by anomalous-dispersion effects, but has been assigned by reference to an unchanging chiral centre in the synthetic procedure. Intra-molecular O-H⋯O hydrogen bonds stabilize the mol-ecular conformation. In the crystal, O-H⋯O hydrogen bonds link the main mol-ecules and the water mol-ecules, 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-Pujić 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 = 338.39

Orthorhombic,

a = 8.2727 (11) Å

b = 24.579 (3) Å

c = 9.3703 (14) Å

V = 1905.3 (5) Å3

Z = 4

Mo Kα radiation

μ = 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 > 2σ(I)

R int = 0.109

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.134

S = 0.90

4626 reflections

225 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.15 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812018168/fj2544sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812018168/fj2544Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812018168/fj2544Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C18H24O5·H2O	F(000) = 728
Mr = 338.39	Dx = 1.180 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 5584 reflections
a = 8.2727 (11) Å	θ = 2.3–25.7°
b = 24.579 (3) Å	µ = 0.09 mm−1
c = 9.3703 (14) Å	T = 296 K
V = 1905.3 (5) Å3	Block, colourless
Z = 4	0.45 × 0.25 × 0.1 mm

Bruker APEXII CCD diffractometer	4626 independent reflections
Radiation source: fine-focus sealed tube	2870 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.109
φ and ω scans	θmax = 28.2°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −10→10
Tmin = 0.151, Tmax = 0.477	k = −32→23
20473 measured reflections	l = −12→12

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ2(Fo2) + (0.0708P)2] where P = (Fo2 + 2Fc2)/3
4626 reflections	(Δ/σ)max = 0.001
225 parameters	Δρmax = 0.18 e Å−3
3 restraints	Δρmin = −0.15 e Å−3

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	−0.02619 (16)	0.98111 (5)	0.36315 (17)	0.0478 (4)
O2	−0.16664 (17)	1.05917 (5)	0.35375 (17)	0.0554 (4)
O3	0.1136 (3)	0.77977 (7)	0.4127 (2)	0.0839 (6)
O4	0.5417 (2)	1.15308 (6)	0.4798 (2)	0.0680 (5)
H4A	0.5221	1.1805	0.5264	0.102*
O5	−0.03447 (19)	1.14487 (6)	0.46197 (19)	0.0616 (4)
H5A	−0.1084	1.1253	0.4345	0.092*
C1	−0.0353 (2)	1.03555 (8)	0.3654 (2)	0.0425 (5)
C2	−0.2267 (3)	0.95504 (10)	0.1831 (2)	0.0589 (6)
H2A	−0.2494	0.9924	0.1610	0.088*
H2B	−0.3218	0.9335	0.1667	0.088*
H2C	−0.1406	0.9422	0.1232	0.088*
C3	−0.1771 (2)	0.95029 (8)	0.3378 (2)	0.0455 (5)
H3A	−0.2632	0.9647	0.3988	0.055*
C4	−0.1378 (3)	0.89190 (8)	0.3826 (2)	0.0505 (5)
H4B	−0.2274	0.8687	0.3553	0.061*
H4C	−0.0435	0.8799	0.3299	0.061*
C5	−0.1054 (3)	0.88393 (8)	0.5415 (2)	0.0552 (5)
H5B	−0.2021	0.8935	0.5945	0.066*
H5C	−0.0201	0.9086	0.5708	0.066*
C6	−0.0556 (3)	0.82491 (9)	0.5808 (3)	0.0654 (7)
H6A	−0.0491	0.8215	0.6837	0.078*
H6B	−0.1377	0.7998	0.5470	0.078*
C7	0.1051 (3)	0.80991 (8)	0.5160 (3)	0.0589 (6)
C8	0.2570 (3)	0.83280 (9)	0.5834 (3)	0.0615 (6)
H8A	0.2925	0.8081	0.6578	0.074*
H8B	0.2305	0.8672	0.6284	0.074*
C9	0.3968 (3)	0.84196 (8)	0.4802 (3)	0.0694 (7)
H9A	0.4214	0.8079	0.4328	0.083*
H9B	0.4916	0.8526	0.5344	0.083*
C10	0.3630 (3)	0.88553 (8)	0.3663 (3)	0.0606 (6)
H10A	0.4530	0.8861	0.3000	0.073*
H10B	0.2675	0.8749	0.3132	0.073*
C11	0.3374 (3)	0.94306 (7)	0.4230 (2)	0.0507 (5)
H11A	0.4313	0.9536	0.4786	0.061*
H11B	0.2447	0.9431	0.4863	0.061*
C12	0.3099 (3)	0.98564 (7)	0.3038 (2)	0.0464 (5)
H12A	0.4046	0.9868	0.2428	0.056*
H12B	0.2187	0.9744	0.2458	0.056*
C13	0.4138 (3)	1.07391 (8)	0.3932 (2)	0.0477 (5)
H13A	0.5159	1.0599	0.3737	0.057*
C14	0.4003 (3)	1.12590 (8)	0.4520 (2)	0.0510 (5)
C15	0.2481 (3)	1.14844 (8)	0.4758 (2)	0.0516 (5)
H15A	0.2387	1.1831	0.5144	0.062*
C16	0.1105 (3)	1.11881 (8)	0.4414 (2)	0.0463 (5)
C17	0.1200 (2)	1.06443 (7)	0.3887 (2)	0.0410 (5)
C18	0.2776 (2)	1.04239 (7)	0.3628 (2)	0.0415 (4)
O6	0.4912 (3)	1.24388 (7)	0.6343 (2)	0.1064 (8)
H6C	0.458 (5)	1.2351 (13)	0.730 (2)	0.162 (17)*
H6D	0.484 (5)	1.2781 (8)	0.585 (3)	0.142 (14)*

	U11	U22	U33	U12	U13	U23
O1	0.0409 (7)	0.0411 (7)	0.0614 (9)	0.0008 (6)	−0.0041 (7)	0.0008 (7)
O2	0.0449 (8)	0.0494 (7)	0.0720 (10)	0.0083 (6)	0.0012 (8)	0.0019 (7)
O3	0.1077 (16)	0.0612 (10)	0.0827 (13)	0.0028 (10)	−0.0138 (12)	−0.0180 (10)
O4	0.0628 (10)	0.0552 (9)	0.0859 (13)	−0.0091 (8)	−0.0132 (9)	−0.0058 (9)
O5	0.0568 (9)	0.0424 (7)	0.0856 (12)	0.0099 (7)	0.0087 (9)	−0.0011 (8)
C1	0.0454 (11)	0.0442 (10)	0.0379 (10)	0.0057 (9)	0.0052 (10)	0.0050 (9)
C2	0.0575 (14)	0.0706 (14)	0.0487 (12)	0.0015 (11)	−0.0035 (11)	−0.0040 (11)
C3	0.0379 (10)	0.0493 (10)	0.0493 (12)	−0.0020 (9)	0.0003 (10)	−0.0056 (9)
C4	0.0491 (13)	0.0473 (11)	0.0551 (13)	−0.0063 (9)	−0.0022 (11)	−0.0060 (9)
C5	0.0613 (14)	0.0511 (11)	0.0531 (13)	−0.0053 (11)	0.0037 (13)	0.0009 (10)
C6	0.0741 (16)	0.0544 (13)	0.0676 (16)	−0.0143 (12)	−0.0036 (14)	0.0111 (11)
C7	0.0837 (17)	0.0355 (9)	0.0574 (14)	−0.0020 (11)	−0.0090 (14)	0.0074 (10)
C8	0.0753 (16)	0.0467 (11)	0.0627 (15)	0.0016 (11)	−0.0158 (14)	0.0093 (11)
C9	0.0693 (16)	0.0412 (11)	0.098 (2)	0.0113 (11)	0.0005 (16)	0.0084 (12)
C10	0.0639 (15)	0.0454 (11)	0.0725 (16)	0.0075 (10)	0.0122 (14)	0.0020 (11)
C11	0.0510 (12)	0.0391 (10)	0.0622 (13)	0.0030 (9)	−0.0041 (11)	0.0017 (9)
C12	0.0448 (11)	0.0426 (10)	0.0517 (12)	0.0038 (9)	0.0053 (10)	−0.0010 (9)
C13	0.0441 (11)	0.0449 (10)	0.0541 (13)	0.0032 (9)	−0.0006 (10)	0.0044 (9)
C14	0.0553 (13)	0.0465 (10)	0.0511 (13)	−0.0085 (10)	−0.0081 (12)	0.0078 (10)
C15	0.0659 (14)	0.0341 (9)	0.0548 (13)	−0.0002 (10)	0.0007 (12)	−0.0004 (9)
C16	0.0535 (12)	0.0386 (9)	0.0469 (12)	0.0071 (9)	0.0053 (11)	0.0091 (9)
C17	0.0452 (11)	0.0381 (9)	0.0398 (11)	0.0024 (8)	0.0015 (10)	0.0070 (8)
C18	0.0476 (11)	0.0379 (9)	0.0391 (10)	0.0032 (8)	0.0003 (10)	0.0078 (8)
O6	0.187 (3)	0.0491 (10)	0.0833 (15)	−0.0237 (12)	0.0217 (17)	0.0017 (10)

O1—C1	1.340 (2)	C8—C9	1.524 (4)
O1—C3	1.479 (2)	C8—H8A	0.9700
O2—C1	1.237 (2)	C8—H8B	0.9700
O3—C7	1.221 (3)	C9—C10	1.538 (3)
O4—C14	1.372 (3)	C9—H9A	0.9700
O4—H4A	0.8200	C9—H9B	0.9700
O5—C16	1.373 (3)	C10—C11	1.525 (3)
O5—H5A	0.8200	C10—H10A	0.9700
C1—C17	1.484 (3)	C10—H10B	0.9700
C2—C3	1.511 (3)	C11—C12	1.548 (3)
C2—H2A	0.9600	C11—H11A	0.9700
C2—H2B	0.9600	C11—H11B	0.9700
C2—H2C	0.9600	C12—C18	1.524 (3)
C3—C4	1.531 (3)	C12—H12A	0.9700
C3—H3A	0.9800	C12—H12B	0.9700
C4—C5	1.525 (3)	C13—C18	1.396 (3)
C4—H4B	0.9700	C13—C14	1.396 (3)
C4—H4C	0.9700	C13—H13A	0.9300
C5—C6	1.552 (3)	C14—C15	1.394 (3)
C5—H5B	0.9700	C15—C16	1.389 (3)
C5—H5C	0.9700	C15—H15A	0.9300
C6—C7	1.507 (4)	C16—C17	1.427 (3)
C6—H6A	0.9700	C17—C18	1.433 (3)
C6—H6B	0.9700	O6—H6C	0.960 (10)
C7—C8	1.515 (3)	O6—H6D	0.961 (10)
C1—O1—C3	117.78 (15)	H8A—C8—H8B	107.5
C14—O4—H4A	109.5	C8—C9—C10	113.91 (19)
C16—O5—H5A	109.5	C8—C9—H9A	108.8
O2—C1—O1	121.12 (18)	C10—C9—H9A	108.8
O2—C1—C17	123.31 (17)	C8—C9—H9B	108.8
O1—C1—C17	115.53 (16)	C10—C9—H9B	108.8
C3—C2—H2A	109.5	H9A—C9—H9B	107.7
C3—C2—H2B	109.5	C11—C10—C9	115.4 (2)
H2A—C2—H2B	109.5	C11—C10—H10A	108.4
C3—C2—H2C	109.5	C9—C10—H10A	108.4
H2A—C2—H2C	109.5	C11—C10—H10B	108.4
H2B—C2—H2C	109.5	C9—C10—H10B	108.4
O1—C3—C2	110.14 (18)	H10A—C10—H10B	107.5
O1—C3—C4	104.88 (15)	C10—C11—C12	113.32 (19)
C2—C3—C4	113.18 (18)	C10—C11—H11A	108.9
O1—C3—H3A	109.5	C12—C11—H11A	108.9
C2—C3—H3A	109.5	C10—C11—H11B	108.9
C4—C3—H3A	109.5	C12—C11—H11B	108.9
C5—C4—C3	115.21 (17)	H11A—C11—H11B	107.7
C5—C4—H4B	108.5	C18—C12—C11	112.51 (17)
C3—C4—H4B	108.5	C18—C12—H12A	109.1
C5—C4—H4C	108.5	C11—C12—H12A	109.1
C3—C4—H4C	108.5	C18—C12—H12B	109.1
H4B—C4—H4C	107.5	C11—C12—H12B	109.1
C4—C5—C6	113.45 (18)	H12A—C12—H12B	107.8
C4—C5—H5B	108.9	C18—C13—C14	121.60 (19)
C6—C5—H5B	108.9	C18—C13—H13A	119.2
C4—C5—H5C	108.9	C14—C13—H13A	119.2
C6—C5—H5C	108.9	O4—C14—C15	123.12 (18)
H5B—C5—H5C	107.7	O4—C14—C13	116.9 (2)
C7—C6—C5	111.56 (19)	C15—C14—C13	119.94 (19)
C7—C6—H6A	109.3	C16—C15—C14	119.67 (18)
C5—C6—H6A	109.3	C16—C15—H15A	120.2
C7—C6—H6B	109.3	C14—C15—H15A	120.2
C5—C6—H6B	109.3	O5—C16—C15	116.03 (17)
H6A—C6—H6B	108.0	O5—C16—C17	122.26 (19)
O3—C7—C6	121.3 (2)	C15—C16—C17	121.71 (19)
O3—C7—C8	120.5 (3)	C16—C17—C18	117.60 (18)
C6—C7—C8	118.2 (2)	C16—C17—C1	116.80 (17)
C7—C8—C9	114.8 (2)	C18—C17—C1	125.60 (16)
C7—C8—H8A	108.6	C13—C18—C17	119.32 (17)
C9—C8—H8A	108.6	C13—C18—C12	116.14 (17)
C7—C8—H8B	108.6	C17—C18—C12	124.54 (17)
C9—C8—H8B	108.6	H6C—O6—H6D	128.6 (19)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O6	0.82	1.87	2.693 (2)	176
O5—H5A···O2	0.82	1.86	2.581 (2)	147
O6—H6C···O3i	0.96 (2)	1.85 (2)	2.810 (3)	178 (3)
O6—H6D···O5ii	0.96 (2)	1.95 (2)	2.887 (2)	164 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O6	0.82	1.87	2.693 (2)	176
O5—H5A⋯O2	0.82	1.86	2.581 (2)	147
O6—H6C⋯O3i	0.96 (2)	1.85 (2)	2.810 (3)	178 (3)
O6—H6D⋯O5ii	0.96 (2)	1.95 (2)	2.887 (2)	164 (2)

Symmetry codes: (i) ; (ii) .