(4S,8S,9R,12E)-8,9,16,18-Tetrahydroxy-4-methyl-3-oxabicyclo[12.4.0]octadeca-12,14,16,18-tetraen-2-one monohydrate.

The asymmetric unit of the title compound, C(18)H(24)O(6)·H(2)O, contains a 14-membered macrolide mol-ecule and a water mol-ecule. In the crystal structure, intra-molecular C-H⋯O and O-H⋯O hydrogen bonds help to stabilize the mol-ecular conformation, while inter-molecular O-H⋯O hydrogen bonds link the mol-ecules, forming an infinite network. The absolute configuration was assigned by comparison with related zearalenone compounds, but needs verification.

Related literature

For the extraction of the components of Fusarium sp. 05ABR26 see: Zhao et al. (2008 ▶). For the crystal structure of zearalenol, see: Gelo-Pujić et al. (1994 ▶). For related zearalenone series compounds, see: Zinedine et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C18H24O6·H2O

M = 354.39

Monoclinic,

a = 18.23 (1) Å

b = 8.078 (6) Å

c = 13.86 (1) Å

β = 118.441 (7)°

V = 1795 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 293 (2) K

0.20 × 0.15 × 0.05 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.980, T max = 0.995

4458 measured reflections

2076 independent reflections

1804 reflections with I > 2σ(I)

R int = 0.081

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.145

S = 1.03

2076 reflections

239 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.36 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SMART; data reduction: SAINT (Bruker, 2000 ▶); 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 datablocks global, I. DOI: 10.1107/S1600536808010258/im2058sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808010258/im2058Isup2.hkl

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

C18H24O6·H2O	F(000) = 760
Mr = 354.39	Dx = 1.312 Mg m−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 687 reflections
a = 18.23 (1) Å	θ = 2.3–26.4°
b = 8.078 (6) Å	µ = 0.10 mm−1
c = 13.86 (1) Å	T = 293 K
β = 118.441 (7)°	Prismatic, colorless
V = 1795 (2) Å3	0.20 × 0.15 × 0.05 mm
Z = 4

Bruker SMART APEX CCD area-detector diffractometer	2076 independent reflections
Radiation source: fine-focus sealed tube	1804 reflections with I > 2σ(I)
graphite	Rint = 0.081
φ and ω scans	θmax = 27.0°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→22
Tmin = 0.980, Tmax = 0.995	k = −10→4
4458 measured reflections	l = −17→17

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0914P)2] where P = (Fo2 + 2Fc2)/3
2076 reflections	(Δ/σ)max < 0.001
239 parameters	Δρmax = 0.28 e Å−3
4 restraints	Δρmin = −0.36 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	0.87040 (13)	0.9829 (4)	0.35095 (16)	0.0406 (6)
H1	0.9091	0.9490	0.4085	0.061*
O2	0.57709 (13)	1.0102 (4)	0.17058 (17)	0.0424 (6)
H2	0.5857	1.0188	0.1179	0.064*
O3	0.94597 (14)	0.9208 (5)	0.55690 (19)	0.0555 (9)
O4	0.88077 (12)	0.9851 (4)	0.65316 (15)	0.0393 (6)
O5	0.72723 (16)	1.0005 (5)	0.9735 (2)	0.0633 (10)
H5	0.7609	0.9364	1.0189	0.095*
O6	0.66693 (14)	1.3026 (3)	0.84561 (17)	0.0397 (6)
H6	0.6404	1.3623	0.7923	0.060*
C1	0.79948 (18)	0.9669 (4)	0.4619 (2)	0.0303 (7)
C2	0.79927 (18)	0.9842 (4)	0.3594 (2)	0.0323 (6)
C3	0.72615 (18)	1.0056 (4)	0.2630 (2)	0.0325 (7)
H3	0.7275	1.0229	0.1975	0.039*
C4	0.65057 (18)	1.0013 (4)	0.2639 (2)	0.0329 (7)
C5	0.64859 (18)	0.9820 (5)	0.3630 (2)	0.0339 (7)
H5A	0.5974	0.9807	0.3626	0.041*
C6	0.72118 (18)	0.9649 (4)	0.4615 (2)	0.0307 (6)
C7	0.88176 (18)	0.9540 (5)	0.5598 (2)	0.0348 (8)
C8	0.95973 (17)	0.9717 (5)	0.7566 (2)	0.0371 (8)
H8	0.9929	0.8813	0.7501	0.044*
C9	1.0079 (2)	1.1292 (6)	0.7784 (3)	0.0518 (10)
H9A	0.9748	1.2192	0.7817	0.078*
H9B	1.0214	1.1488	0.7204	0.078*
H9C	1.0583	1.1207	0.8470	0.078*
C10	0.9324 (2)	0.9239 (5)	0.8403 (3)	0.0403 (8)
H10A	0.9817	0.9075	0.9107	0.048*
H10B	0.9031	0.8190	0.8186	0.048*
C11	0.8761 (2)	1.0503 (5)	0.8547 (3)	0.0390 (8)
H11A	0.8391	1.0999	0.7843	0.047*
H11B	0.9100	1.1376	0.9037	0.047*
C12	0.8244 (2)	0.9678 (5)	0.9017 (3)	0.0384 (8)
H12A	0.7921	0.8786	0.8531	0.046*
H12B	0.8621	0.9189	0.9721	0.046*
C13	0.76515 (19)	1.0832 (5)	0.9174 (2)	0.0372 (8)
H13	0.7985	1.1746	0.9643	0.045*
C14	0.69633 (19)	1.1591 (4)	0.8122 (2)	0.0319 (7)
H14	0.7218	1.1976	0.7680	0.038*
C15	0.6218 (2)	1.0502 (5)	0.7392 (3)	0.0402 (8)
H15A	0.6040	0.9934	0.7861	0.048*
H15B	0.5766	1.1225	0.6914	0.048*
C16	0.6333 (2)	0.9202 (5)	0.6675 (3)	0.0394 (8)
H16A	0.6779	0.8464	0.7150	0.047*
H16B	0.5826	0.8549	0.6320	0.047*
C17	0.65289 (19)	0.9846 (5)	0.5803 (2)	0.0365 (7)
H17	0.6211	1.0723	0.5372	0.044*
C18	0.71206 (18)	0.9253 (4)	0.5608 (2)	0.0320 (7)
H18	0.7509	0.8537	0.6124	0.038*
O7	0.58905 (17)	1.0465 (9)	−0.0084 (2)	0.104 (2)
H7X	0.6347 (15)	1.031 (7)	−0.011 (3)	0.065 (14)*
H7Y	0.5433 (15)	1.057 (9)	−0.067 (3)	0.084 (17)*

	U11	U22	U33	U12	U13	U23
O1	0.0283 (10)	0.0658 (18)	0.0285 (10)	0.0009 (12)	0.0143 (9)	−0.0025 (13)
O2	0.0303 (10)	0.0656 (19)	0.0266 (10)	0.0022 (12)	0.0099 (9)	0.0024 (12)
O3	0.0308 (11)	0.105 (3)	0.0311 (11)	0.0088 (14)	0.0150 (10)	−0.0045 (14)
O4	0.0271 (9)	0.0652 (16)	0.0222 (10)	0.0050 (12)	0.0088 (8)	−0.0037 (12)
O5	0.0505 (15)	0.096 (3)	0.0577 (16)	0.0275 (17)	0.0372 (14)	0.0453 (18)
O6	0.0403 (13)	0.0473 (14)	0.0316 (11)	0.0104 (11)	0.0172 (11)	0.0001 (11)
C1	0.0296 (13)	0.0349 (18)	0.0239 (12)	0.0002 (13)	0.0108 (11)	−0.0028 (13)
C2	0.0337 (14)	0.0363 (17)	0.0280 (13)	−0.0036 (15)	0.0156 (12)	−0.0052 (15)
C3	0.0355 (15)	0.0392 (18)	0.0258 (12)	0.0005 (14)	0.0170 (12)	−0.0004 (13)
C4	0.0308 (14)	0.0371 (18)	0.0265 (13)	0.0024 (14)	0.0102 (12)	−0.0022 (13)
C5	0.0271 (13)	0.0457 (18)	0.0303 (14)	0.0007 (14)	0.0147 (12)	−0.0017 (15)
C6	0.0328 (14)	0.0345 (17)	0.0261 (13)	0.0015 (13)	0.0150 (12)	−0.0022 (12)
C7	0.0297 (14)	0.048 (2)	0.0275 (14)	0.0016 (14)	0.0139 (12)	−0.0025 (14)
C8	0.0240 (13)	0.057 (2)	0.0248 (13)	0.0109 (15)	0.0072 (12)	0.0000 (15)
C9	0.0408 (19)	0.071 (3)	0.047 (2)	−0.0069 (19)	0.0238 (18)	−0.013 (2)
C10	0.0356 (16)	0.053 (2)	0.0302 (15)	0.0129 (16)	0.0139 (13)	0.0081 (15)
C11	0.0377 (16)	0.045 (2)	0.0397 (16)	0.0036 (15)	0.0230 (15)	0.0020 (15)
C12	0.0326 (14)	0.045 (2)	0.0354 (15)	0.0080 (15)	0.0141 (13)	0.0100 (15)
C13	0.0317 (15)	0.054 (2)	0.0304 (15)	0.0018 (15)	0.0182 (14)	0.0059 (14)
C14	0.0310 (14)	0.0415 (18)	0.0287 (14)	0.0015 (13)	0.0187 (13)	0.0002 (13)
C15	0.0379 (16)	0.053 (2)	0.0370 (16)	−0.0036 (16)	0.0234 (15)	−0.0040 (16)
C16	0.0408 (17)	0.0452 (19)	0.0349 (16)	−0.0130 (16)	0.0202 (15)	−0.0087 (15)
C17	0.0375 (15)	0.0431 (18)	0.0295 (14)	−0.0029 (15)	0.0165 (13)	−0.0035 (15)
C18	0.0291 (14)	0.0382 (17)	0.0247 (14)	−0.0044 (13)	0.0096 (12)	−0.0011 (12)
O7	0.0298 (13)	0.252 (6)	0.0303 (13)	0.005 (3)	0.0133 (12)	0.005 (3)

O1—C2	1.356 (4)	C9—H9C	0.9599
O1—H1	0.8200	C10—C11	1.526 (5)
O2—C4	1.349 (4)	C10—H10A	0.9700
O2—H2	0.8200	C10—H10B	0.9700
O3—C7	1.220 (4)	C11—C12	1.532 (5)
O4—C7	1.327 (4)	C11—H11A	0.9700
O4—C8	1.474 (3)	C11—H11B	0.9700
O5—C13	1.429 (4)	C12—C13	1.518 (5)
O5—H5	0.8200	C12—H12A	0.9700
O6—C14	1.443 (4)	C12—H12B	0.9700
O6—H6	0.8200	C13—C14	1.527 (4)
C1—C6	1.424 (4)	C13—H13	0.9800
C1—C2	1.426 (4)	C14—C15	1.528 (5)
C1—C7	1.470 (4)	C14—H14	0.9800
C2—C3	1.377 (4)	C15—C16	1.526 (5)
C3—C4	1.384 (4)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.400 (4)	C16—C17	1.507 (4)
C5—C6	1.383 (4)	C16—H16A	0.9700
C5—H5A	0.9300	C16—H16B	0.9700
C6—C18	1.497 (4)	C17—C18	1.321 (5)
C8—C9	1.492 (6)	C17—H17	0.9300
C8—C10	1.514 (5)	C18—H18	0.9300
C8—H8	0.9800	O7—H7X	0.857 (18)
C9—H9A	0.9599	O7—H7Y	0.844 (18)
C9—H9B	0.9599
C2—O1—H1	109.5	C10—C11—C12	110.7 (3)
C4—O2—H2	109.5	C10—C11—H11A	109.5
C7—O4—C8	118.3 (2)	C12—C11—H11A	109.5
C13—O5—H5	109.5	C10—C11—H11B	109.5
C14—O6—H6	109.5	C12—C11—H11B	109.5
C6—C1—C2	118.0 (3)	H11A—C11—H11B	108.1
C6—C1—C7	125.7 (3)	C13—C12—C11	114.7 (3)
C2—C1—C7	116.3 (3)	C13—C12—H12A	108.6
O1—C2—C3	116.2 (2)	C11—C12—H12A	108.6
O1—C2—C1	122.4 (3)	C13—C12—H12B	108.6
C3—C2—C1	121.4 (3)	C11—C12—H12B	108.6
C2—C3—C4	119.8 (3)	H12A—C12—H12B	107.6
C2—C3—H3	120.1	O5—C13—C12	110.6 (3)
C4—C3—H3	120.1	O5—C13—C14	108.5 (2)
O2—C4—C3	121.9 (3)	C12—C13—C14	115.3 (3)
O2—C4—C5	117.9 (3)	O5—C13—H13	107.4
C3—C4—C5	120.1 (3)	C12—C13—H13	107.4
C6—C5—C4	121.3 (3)	C14—C13—H13	107.4
C6—C5—H5A	119.3	O6—C14—C13	106.2 (2)
C4—C5—H5A	119.3	O6—C14—C15	109.1 (3)
C5—C6—C1	119.3 (3)	C13—C14—C15	117.9 (3)
C5—C6—C18	117.1 (3)	O6—C14—H14	107.8
C1—C6—C18	123.2 (3)	C13—C14—H14	107.8
O3—C7—O4	122.2 (3)	C15—C14—H14	107.8
O3—C7—C1	124.0 (3)	C16—C15—C14	118.3 (3)
O4—C7—C1	113.9 (2)	C16—C15—H15A	107.7
O4—C8—C9	110.0 (3)	C14—C15—H15A	107.7
O4—C8—C10	103.8 (2)	C16—C15—H15B	107.7
C9—C8—C10	116.0 (3)	C14—C15—H15B	107.7
O4—C8—H8	108.9	H15A—C15—H15B	107.1
C9—C8—H8	108.9	C17—C16—C15	116.3 (3)
C10—C8—H8	108.9	C17—C16—H16A	108.2
C8—C9—H9A	109.5	C15—C16—H16A	108.2
C8—C9—H9B	109.5	C17—C16—H16B	108.2
H9A—C9—H9B	109.5	C15—C16—H16B	108.2
C8—C9—H9C	109.5	H16A—C16—H16B	107.4
H9A—C9—H9C	109.5	C18—C17—C16	124.6 (3)
H9B—C9—H9C	109.5	C18—C17—H17	117.7
C8—C10—C11	114.6 (3)	C16—C17—H17	117.7
C8—C10—H10A	108.6	C17—C18—C6	124.7 (3)
C11—C10—H10A	108.6	C17—C18—H18	117.6
C8—C10—H10B	108.6	C6—C18—H18	117.6
C11—C10—H10B	108.6	H7X—O7—H7Y	121 (3)
H10A—C10—H10B	107.6
C6—C1—C2—O1	−178.2 (3)	C2—C1—C7—O4	161.9 (3)
C7—C1—C2—O1	2.4 (5)	C7—O4—C8—C9	84.2 (4)
C6—C1—C2—C3	2.7 (5)	C7—O4—C8—C10	−151.0 (3)
C7—C1—C2—C3	−176.7 (3)	O4—C8—C10—C11	−61.1 (4)
O1—C2—C3—C4	177.3 (3)	C9—C8—C10—C11	59.7 (4)
C1—C2—C3—C4	−3.6 (5)	C8—C10—C11—C12	157.2 (3)
C2—C3—C4—O2	−175.3 (3)	C10—C11—C12—C13	−179.1 (3)
C2—C3—C4—C5	2.6 (5)	C11—C12—C13—O5	−173.0 (3)
O2—C4—C5—C6	177.2 (3)	C11—C12—C13—C14	63.5 (4)
C3—C4—C5—C6	−0.8 (6)	O5—C13—C14—O6	74.9 (4)
C4—C5—C6—C1	−0.1 (6)	C12—C13—C14—O6	−160.5 (3)
C4—C5—C6—C18	−173.1 (3)	O5—C13—C14—C15	−47.6 (4)
C2—C1—C6—C5	−0.9 (5)	C12—C13—C14—C15	77.0 (4)
C7—C1—C6—C5	178.5 (3)	O6—C14—C15—C16	162.4 (3)
C2—C1—C6—C18	171.7 (3)	C13—C14—C15—C16	−76.5 (4)
C7—C1—C6—C18	−8.9 (5)	C14—C15—C16—C17	−63.5 (4)
C8—O4—C7—O3	−2.6 (6)	C15—C16—C17—C18	133.7 (4)
C8—O4—C7—C1	178.6 (3)	C16—C17—C18—C6	167.4 (3)
C6—C1—C7—O3	163.7 (4)	C5—C6—C18—C17	−37.0 (5)
C2—C1—C7—O3	−16.9 (5)	C1—C6—C18—C17	150.3 (4)
C6—C1—C7—O4	−17.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O3	0.82	1.85	2.560 (4)	144.
O2—H2···O7	0.82	1.79	2.608 (4)	172.
C3—H3···O7	0.93	2.77	3.398 (4)	125.
C9—H9B···O3	0.96	2.73	3.198 (5)	111.
O1—H1···O3i	0.82	2.46	3.003 (4)	125.
O7—H7Y···O2ii	0.84 (2)	2.01 (3)	2.798 (4)	156 (6)
O5—H5···O6iii	0.82	2.02	2.821 (4)	166.
O6—H6···O1iv	0.82	2.13	2.871 (4)	149.
C3—H3···O6v	0.93	2.88	3.398 (4)	116.
C10—H10B···O2v	0.97	2.52	3.346 (6)	144.
O7—H7X···O5vi	0.86 (2)	1.82 (2)	2.674 (4)	176 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O3	0.82	1.85	2.560 (4)	144
O2—H2⋯O7	0.82	1.79	2.608 (4)	172
C3—H3⋯O7	0.93	2.77	3.398 (4)	125
C9—H9B⋯O3	0.96	2.73	3.198 (5)	111
O1—H1⋯O3i	0.82	2.46	3.003 (4)	125
O7—H7Y⋯O2ii	0.844 (18)	2.01 (3)	2.798 (4)	156 (6)
O5—H5⋯O6iii	0.82	2.02	2.821 (4)	166
O6—H6⋯O1iv	0.82	2.13	2.871 (4)	149
C3—H3⋯O6v	0.93	2.88	3.398 (4)	116
C10—H10B⋯O2v	0.97	2.52	3.346 (6)	144
O7—H7X⋯O5vi	0.857 (18)	1.818 (19)	2.674 (4)	176 (4)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) .