(3S,11Z)-14,16-Dihy-droxy-3-methyl-3,4,5,6,9,10-hexa-hydro-1H-2-benz-oxacyclo-tetra-decine-1,7(8H)-dione (cis-zearalenone): a redetermination.

The title compound, also known as cis-zearalenone (cis-ZEN), C(18)H(22)O(5), has already been reported elsewhere [Griffin et al. (1981 ▶). ACA Ser.29, 35], but no atomic coordinates are publicly available. The mol-ecule is of inter-est with respect to its toxicity. In the crystal, intra-molecular O-H⋯O hydrogen bonds stabilize the mol-ecular conformation, while inter-molecular O-H⋯O hydrogen bonds link the mol-ecules to form infinite chains along the [110] and [1-10] directions. The absolute configuration has been assigned by reference to an unchanging chiral centre in the synthetic procedure.

Related literature

For the crystal structures of trans-zearalenone (trans-ZEN) and zearalenol, see: Gelo-Pujić et al. (1994 ▶) and Zhao et al. (2008 ▶). For more detailed information about trans-ZEN and its metabolites, see: Urry et al. (1966 ▶) and Zinedine et al. (2007 ▶).

Experimental

Crystal data

C18H22O5

M = 318.36

Monoclinic,

a = 5.677 (3) Å

b = 9.186 (4) Å

c = 16.531 (7) Å

β = 98.91 (3)°

V = 851.7 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.3 × 0.1 × 0.05 mm

Data collection

Bruker APEX CCD area-detector diffractometer

Absorption correction: ψ scan (SHELXTL; Sheldrick, 2008 ▶) T min = 0.21, T max = 0.28

20096 measured reflections

1976 independent reflections

1014 reflections with I > 2σ(I)

R int = 0.101

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.124

S = 0.87

1976 reflections

209 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.11 e Å−3

Data collection: SMART (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 (Bruker, 2001 ▶) and ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812002735/bg2443sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812002735/bg2443Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812002735/bg2443Isup3.mol

Supplementary material file. DOI: 10.1107/S1600536812002735/bg2443Isup4.cml

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

C18H22O5	F(000) = 340
Mr = 318.36	Dx = 1.241 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 56 reflections
a = 5.677 (3) Å	θ = 4–25°
b = 9.186 (4) Å	µ = 0.09 mm−1
c = 16.531 (7) Å	T = 296 K
β = 98.91 (3)°	Plate, colourless
V = 851.7 (7) Å3	0.3 × 0.1 × 0.05 mm
Z = 2

Bruker APEX CCD area-detector diffractometer	1976 independent reflections
Radiation source: fine-focus sealed tube	1014 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.101
ω/2θ scans	θmax = 27.0°, θmin = 1.3°
Absorption correction: ψ scan (SHELXTL; Sheldrick, 2008)	h = −7→7
Tmin = 0.21, Tmax = 0.28	k = −11→11
20096 measured reflections	l = −21→21

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124	H-atom parameters constrained
S = 0.87	w = 1/[σ2(Fo2) + (0.0678P)2] where P = (Fo2 + 2Fc2)/3
1976 reflections	(Δ/σ)max < 0.001
209 parameters	Δρmax = 0.14 e Å−3
1 restraint	Δρmin = −0.11 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	0.7716 (4)	0.4105 (3)	0.15608 (15)	0.0636 (7)
O2	0.8395 (5)	0.2441 (3)	0.06309 (17)	0.0829 (9)
O3	0.7827 (6)	0.8046 (4)	0.30820 (19)	0.0888 (10)
O4	1.5275 (5)	0.0183 (3)	0.38175 (16)	0.0758 (9)
H20	1.6166	−0.0360	0.3613	0.114*
O5	1.1936 (6)	0.0703 (4)	0.10159 (17)	0.0871 (9)
H22	1.0861	0.1128	0.0719	0.131*
C1	0.8686 (7)	0.2863 (5)	0.1351 (3)	0.0606 (10)
C2	0.3806 (8)	0.4346 (7)	0.0708 (3)	0.0937 (15)
H4	0.3069	0.4314	0.1192	0.141*
H2	0.3917	0.3377	0.0498	0.141*
H3	0.2863	0.4938	0.0301	0.141*
C3	0.6293 (7)	0.4994 (5)	0.0915 (2)	0.0691 (12)
H1	0.7070	0.5021	0.0426	0.083*
C4	0.6229 (8)	0.6532 (5)	0.1284 (3)	0.0783 (13)
H5	0.5046	0.7097	0.0930	0.094*
H6	0.5681	0.6445	0.1809	0.094*
C5	0.8534 (9)	0.7391 (6)	0.1412 (3)	0.0888 (14)
H8	0.8148	0.8417	0.1434	0.107*
H7	0.9330	0.7245	0.0939	0.107*
C6	1.0269 (8)	0.7005 (6)	0.2177 (3)	0.0814 (13)
H9	1.0458	0.5956	0.2189	0.098*
H10	1.1806	0.7419	0.2120	0.098*
C7	0.9691 (9)	0.7467 (4)	0.2989 (3)	0.0684 (11)
C8	1.1633 (9)	0.7214 (6)	0.3731 (3)	0.0950 (15)
H12	1.2920	0.6674	0.3547	0.114*
H11	1.2269	0.8154	0.3922	0.114*
C9	1.0909 (10)	0.6422 (5)	0.4445 (3)	0.0876 (14)
H13	0.9359	0.6776	0.4533	0.105*
H14	1.2040	0.6649	0.4931	0.105*
C10	1.0780 (9)	0.4767 (4)	0.4340 (3)	0.0770 (13)
H16	1.2174	0.4438	0.4119	0.092*
H15	1.0820	0.4318	0.4873	0.092*
C11	0.8601 (7)	0.4273 (4)	0.3791 (2)	0.0613 (10)
H17	0.7185	0.4688	0.3897	0.074*
C12	0.8360 (7)	0.3329 (4)	0.3171 (2)	0.0549 (10)
H18	0.6828	0.3230	0.2881	0.066*
C13	1.1930 (7)	0.1716 (4)	0.3452 (2)	0.0578 (10)
H19	1.1928	0.1882	0.4007	0.069*
C14	1.3643 (7)	0.0777 (4)	0.3214 (2)	0.0590 (10)
C15	1.3633 (7)	0.0455 (4)	0.2402 (3)	0.0643 (11)
H21	1.4758	−0.0179	0.2246	0.077*
C16	1.1909 (8)	0.1094 (4)	0.1815 (2)	0.0648 (11)
C17	1.0217 (7)	0.2105 (4)	0.2032 (2)	0.0535 (9)
C18	1.0224 (6)	0.2411 (4)	0.2881 (2)	0.0516 (9)

	U11	U22	U33	U12	U13	U23
O1	0.0711 (17)	0.0634 (17)	0.0536 (15)	0.0035 (16)	0.0008 (12)	0.0067 (14)
O2	0.097 (2)	0.097 (2)	0.0508 (17)	0.0073 (19)	−0.0019 (15)	−0.0117 (16)
O3	0.093 (2)	0.078 (2)	0.097 (2)	0.024 (2)	0.0210 (19)	0.0020 (18)
O4	0.0816 (19)	0.0612 (18)	0.0781 (19)	0.0113 (15)	−0.0079 (15)	0.0037 (15)
O5	0.110 (2)	0.088 (2)	0.0641 (18)	0.018 (2)	0.0173 (16)	−0.0149 (16)
C1	0.059 (2)	0.064 (3)	0.059 (3)	−0.004 (2)	0.009 (2)	−0.002 (2)
C2	0.072 (3)	0.110 (4)	0.093 (3)	−0.001 (3)	−0.007 (2)	0.004 (3)
C3	0.063 (3)	0.082 (3)	0.059 (2)	0.002 (2)	0.0022 (19)	0.015 (2)
C4	0.077 (3)	0.081 (3)	0.076 (3)	0.012 (3)	0.012 (2)	0.025 (3)
C5	0.101 (4)	0.080 (3)	0.089 (3)	−0.001 (3)	0.028 (3)	0.014 (3)
C6	0.075 (3)	0.065 (3)	0.103 (4)	−0.003 (2)	0.009 (3)	−0.004 (3)
C7	0.085 (3)	0.045 (2)	0.076 (3)	−0.005 (2)	0.015 (2)	0.002 (2)
C8	0.084 (3)	0.084 (3)	0.109 (4)	−0.013 (3)	−0.009 (3)	0.014 (3)
C9	0.130 (4)	0.052 (2)	0.074 (3)	−0.001 (3)	−0.005 (3)	−0.006 (2)
C10	0.112 (4)	0.049 (2)	0.065 (3)	−0.001 (2)	−0.001 (2)	−0.001 (2)
C11	0.079 (3)	0.053 (2)	0.053 (2)	0.002 (2)	0.0143 (19)	0.002 (2)
C12	0.058 (2)	0.054 (2)	0.053 (2)	−0.0043 (19)	0.0102 (18)	0.0073 (19)
C13	0.075 (3)	0.047 (2)	0.051 (2)	−0.007 (2)	0.009 (2)	−0.0010 (18)
C14	0.072 (3)	0.043 (2)	0.061 (3)	−0.009 (2)	0.005 (2)	−0.001 (2)
C15	0.069 (3)	0.047 (2)	0.077 (3)	0.006 (2)	0.011 (2)	−0.003 (2)
C16	0.084 (3)	0.055 (3)	0.059 (3)	−0.007 (2)	0.021 (2)	−0.011 (2)
C17	0.060 (2)	0.049 (2)	0.051 (2)	−0.0067 (19)	0.0063 (18)	−0.0027 (17)
C18	0.060 (2)	0.042 (2)	0.054 (2)	−0.0102 (19)	0.0100 (18)	0.0021 (18)

O1—C1	1.336 (5)	C6—H10	0.9700
O1—C3	1.480 (4)	C7—C8	1.535 (6)
O2—C1	1.238 (4)	C8—C9	1.497 (7)
O3—C7	1.215 (5)	C8—H12	0.9700
O4—C14	1.366 (4)	C8—H11	0.9700
O4—H20	0.8200	C9—C10	1.531 (6)
O5—C16	1.371 (4)	C9—H13	0.9700
O5—H22	0.8200	C9—H14	0.9700
C1—C17	1.485 (5)	C10—C11	1.487 (6)
C2—C3	1.522 (6)	C10—H16	0.9700
C2—H4	0.9600	C10—H15	0.9700
C2—H2	0.9600	C11—C12	1.334 (5)
C2—H3	0.9600	C11—H17	0.9300
C3—C4	1.542 (6)	C12—C18	1.488 (5)
C3—H1	0.9800	C12—H18	0.9300
C4—C5	1.514 (6)	C13—C18	1.398 (5)
C4—H5	0.9700	C13—C14	1.401 (5)
C4—H6	0.9700	C13—H19	0.9300
C5—C6	1.521 (6)	C14—C15	1.373 (5)
C5—H8	0.9700	C15—C16	1.397 (5)
C5—H7	0.9700	C15—H21	0.9300
C6—C7	1.491 (6)	C16—C17	1.422 (5)
C6—H9	0.9700	C17—C18	1.432 (5)
C1—O1—C3	119.0 (3)	C7—C8—H12	108.1
C14—O4—H20	109.5	C9—C8—H11	108.1
C16—O5—H22	109.5	C7—C8—H11	108.1
O2—C1—O1	121.2 (4)	H12—C8—H11	107.3
O2—C1—C17	123.9 (4)	C8—C9—C10	114.0 (4)
O1—C1—C17	114.9 (3)	C8—C9—H13	108.7
C3—C2—H4	109.5	C10—C9—H13	108.7
C3—C2—H2	109.5	C8—C9—H14	108.7
H4—C2—H2	109.5	C10—C9—H14	108.7
C3—C2—H3	109.5	H13—C9—H14	107.6
H4—C2—H3	109.5	C11—C10—C9	113.1 (4)
H2—C2—H3	109.5	C11—C10—H16	109.0
O1—C3—C2	109.3 (3)	C9—C10—H16	109.0
O1—C3—C4	105.3 (3)	C11—C10—H15	109.0
C2—C3—C4	111.7 (4)	C9—C10—H15	109.0
O1—C3—H1	110.1	H16—C10—H15	107.8
C2—C3—H1	110.1	C12—C11—C10	130.1 (4)
C4—C3—H1	110.1	C12—C11—H17	115.0
C5—C4—C3	117.4 (4)	C10—C11—H17	115.0
C5—C4—H5	108.0	C11—C12—C18	128.5 (4)
C3—C4—H5	108.0	C11—C12—H18	115.8
C5—C4—H6	108.0	C18—C12—H18	115.8
C3—C4—H6	108.0	C18—C13—C14	122.0 (3)
H5—C4—H6	107.2	C18—C13—H19	119.0
C4—C5—C6	115.4 (4)	C14—C13—H19	119.0
C4—C5—H8	108.4	O4—C14—C15	121.8 (4)
C6—C5—H8	108.4	O4—C14—C13	117.5 (3)
C4—C5—H7	108.4	C15—C14—C13	120.6 (4)
C6—C5—H7	108.4	C14—C15—C16	119.0 (4)
H8—C5—H7	107.5	C14—C15—H21	120.5
C7—C6—C5	118.6 (4)	C16—C15—H21	120.5
C7—C6—H9	107.7	O5—C16—C15	116.7 (4)
C5—C6—H9	107.7	O5—C16—C17	121.5 (4)
C7—C6—H10	107.7	C15—C16—C17	121.8 (4)
C5—C6—H10	107.7	C16—C17—C18	118.5 (3)
H9—C6—H10	107.1	C16—C17—C1	117.0 (3)
O3—C7—C6	123.8 (4)	C18—C17—C1	124.3 (3)
O3—C7—C8	119.8 (4)	C13—C18—C17	118.0 (3)
C6—C7—C8	116.4 (4)	C13—C18—C12	119.6 (3)
C9—C8—C7	116.9 (4)	C17—C18—C12	122.2 (3)
C9—C8—H12	108.1
C3—O1—C1—O2	−0.7 (5)	C13—C14—C15—C16	0.9 (6)
C3—O1—C1—C17	175.9 (3)	C14—C15—C16—O5	−178.2 (3)
C1—O1—C3—C2	79.8 (4)	C14—C15—C16—C17	2.2 (6)
C1—O1—C3—C4	−160.1 (3)	O5—C16—C17—C18	177.2 (3)
O1—C3—C4—C5	69.7 (4)	C15—C16—C17—C18	−3.2 (6)
C2—C3—C4—C5	−171.8 (4)	O5—C16—C17—C1	−7.7 (5)
C3—C4—C5—C6	−80.4 (5)	C15—C16—C17—C1	171.9 (4)
C4—C5—C6—C7	−72.6 (6)	O2—C1—C17—C16	17.5 (6)
C5—C6—C7—O3	5.5 (6)	O1—C1—C17—C16	−159.0 (3)
C5—C6—C7—C8	−172.9 (4)	O2—C1—C17—C18	−167.7 (4)
O3—C7—C8—C9	53.2 (6)	O1—C1—C17—C18	15.8 (5)
C6—C7—C8—C9	−128.3 (5)	C14—C13—C18—C17	1.9 (5)
C7—C8—C9—C10	80.1 (6)	C14—C13—C18—C12	176.4 (3)
C8—C9—C10—C11	−77.0 (6)	C16—C17—C18—C13	1.1 (5)
C9—C10—C11—C12	132.8 (5)	C1—C17—C18—C13	−173.6 (3)
C10—C11—C12—C18	4.5 (7)	C16—C17—C18—C12	−173.3 (3)
C18—C13—C14—O4	178.2 (3)	C1—C17—C18—C12	12.0 (5)
C18—C13—C14—C15	−3.0 (6)	C11—C12—C18—C13	41.9 (6)
O4—C14—C15—C16	179.7 (3)	C11—C12—C18—C17	−143.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H22···O2	0.82	1.84	2.569 (5)	148
O4—H20···O3i	0.82	2.01	2.824 (5)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H22⋯O2	0.82	1.84	2.569 (5)	148
O4—H20⋯O3i	0.82	2.01	2.824 (5)	169

Symmetry code: (i) .