Oosporein from Tremella fuciformis.

THE TITLE COMPOUND [SYSTEMATIC NAME: 3,3',6,6'-tetra-hydroxy-4,4'-dimethyl-1,1'-bi(cyclo-hexa-3,6-diene)-2,2',5,5'-tetra-one], C(14)H(10)O(8), was isolated from Tremella fuciformis. The mol-ecule has 2 symmetry, with the mid-point of the C-C bond linking the cyclo-hexa-dienedione rings located on a twofold rotation axis. In the mol-ecule, the ring is approximately planar, with an r.m.s. deviation of 0.0093 Å, and the two rings make a dihedral angle of 67.89 (5)°. Inter-molecular O-H⋯O hydrogen bonding occurs in the crystal structure.

Related literature

For general background to the title compound, see: Takeshita & Anchel (1965 ▶). For the chemical structure of the title compound established from NMR data, see: Richard et al. (1974 ▶).

Experimental

Crystal data

C14H10O8

M = 306.22

Monoclinic,

a = 11.9983 (9) Å

b = 8.2981 (6) Å

c = 13.7634 (11) Å

β = 105.994 (7)°

V = 1317.28 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 293 K

0.25 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

2848 measured reflections

1342 independent reflections

937 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.118

S = 1.06

1342 reflections

103 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.17 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2009 ▶); program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812012950/xu5486sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812012950/xu5486Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812012950/xu5486Isup3.cml

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

C14H10O8	F(000) = 632
Mr = 306.22	Dx = 1.544 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.9983 (9) Å	Cell parameters from 884 reflections
b = 8.2981 (6) Å	θ = 3.0–28.7°
c = 13.7634 (11) Å	µ = 0.13 mm−1
β = 105.994 (7)°	T = 293 K
V = 1317.28 (17) Å3	Block, colorless
Z = 4	0.25 × 0.20 × 0.20 mm

Oxford Diffraction Xcalibur Eos diffractometer	937 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.022
Graphite monochromator	θmax = 26.4°, θmin = 3.0°
Detector resolution: 10.0 pixels mm-1	h = −14→11
ω scans	k = −9→10
2848 measured reflections	l = −17→13
1342 independent reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0491P)2 + 0.4579P] where P = (Fo2 + 2Fc2)/3
1342 reflections	(Δ/σ)max < 0.001
103 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.17 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	0.82546 (12)	0.06885 (18)	0.65807 (11)	0.0380 (4)
O2	0.79548 (13)	0.0605 (2)	0.45935 (11)	0.0434 (5)
H2	0.7623	0.0135	0.4958	0.065*
O3	1.16014 (12)	0.3820 (2)	0.71051 (11)	0.0402 (5)
H3	1.1965	0.4229	0.6744	0.060*
O4	1.12577 (13)	0.3814 (2)	0.51152 (12)	0.0454 (5)
C1	0.95888 (17)	0.2202 (2)	0.47435 (15)	0.0275 (5)
C2	0.88498 (16)	0.1437 (2)	0.51643 (15)	0.0274 (5)
C3	0.89706 (16)	0.1438 (2)	0.62776 (15)	0.0259 (5)
C4	0.99324 (15)	0.2298 (2)	0.69505 (14)	0.0232 (5)
C5	1.06929 (16)	0.3034 (2)	0.65361 (15)	0.0267 (5)
C6	1.05442 (17)	0.3056 (2)	0.54165 (16)	0.0284 (5)
C7	0.9473 (2)	0.2204 (3)	0.36334 (16)	0.0399 (6)
H7A	0.9064	0.1254	0.3332	0.060*
H7B	1.0229	0.2215	0.3525	0.060*
H7C	0.9050	0.3144	0.3331	0.060*

	U11	U22	U33	U12	U13	U23
O1	0.0323 (8)	0.0499 (10)	0.0336 (9)	−0.0172 (7)	0.0120 (7)	0.0003 (7)
O2	0.0398 (9)	0.0616 (12)	0.0274 (9)	−0.0259 (8)	0.0069 (7)	−0.0044 (8)
O3	0.0339 (9)	0.0544 (11)	0.0309 (9)	−0.0219 (7)	0.0066 (7)	−0.0014 (8)
O4	0.0416 (9)	0.0618 (11)	0.0351 (10)	−0.0259 (8)	0.0146 (7)	−0.0008 (8)
C1	0.0264 (10)	0.0320 (12)	0.0243 (11)	−0.0007 (9)	0.0074 (8)	−0.0006 (9)
C2	0.0236 (10)	0.0315 (12)	0.0259 (12)	−0.0045 (9)	0.0047 (8)	−0.0013 (9)
C3	0.0227 (10)	0.0269 (11)	0.0286 (12)	0.0003 (8)	0.0080 (8)	0.0034 (8)
C4	0.0223 (10)	0.0247 (11)	0.0227 (11)	0.0019 (8)	0.0064 (8)	0.0009 (8)
C5	0.0220 (10)	0.0289 (11)	0.0274 (12)	−0.0033 (8)	0.0040 (8)	−0.0019 (9)
C6	0.0260 (11)	0.0299 (12)	0.0313 (12)	−0.0024 (9)	0.0112 (9)	0.0018 (9)
C7	0.0424 (13)	0.0499 (15)	0.0291 (13)	−0.0063 (11)	0.0125 (10)	−0.0024 (11)

O1—C3	1.223 (2)	C2—C3	1.499 (3)
O2—C2	1.335 (2)	C3—C4	1.452 (3)
O2—H2	0.8200	C4—C5	1.348 (3)
O3—C5	1.325 (2)	C4—C4i	1.476 (4)
O3—H3	0.8200	C5—C6	1.502 (3)
O4—C6	1.223 (2)	C7—H7A	0.9600
C1—C2	1.344 (3)	C7—H7B	0.9600
C1—C6	1.445 (3)	C7—H7C	0.9600
C1—C7	1.496 (3)
C2—O2—H2	109.5	C3—C4—C4i	119.81 (18)
C5—O3—H3	109.5	O3—C5—C4	121.01 (18)
C2—C1—C6	117.14 (18)	O3—C5—C6	116.50 (17)
C2—C1—C7	123.62 (18)	C4—C5—C6	122.46 (17)
C6—C1—C7	119.24 (18)	O4—C6—C1	122.71 (19)
O2—C2—C1	120.65 (18)	O4—C6—C5	117.24 (18)
O2—C2—C3	115.94 (16)	C1—C6—C5	120.04 (17)
C1—C2—C3	123.41 (17)	C1—C7—H7A	109.5
O1—C3—C4	122.79 (19)	C1—C7—H7B	109.5
O1—C3—C2	117.97 (17)	H7A—C7—H7B	109.5
C4—C3—C2	119.23 (17)	C1—C7—H7C	109.5
C5—C4—C3	117.65 (18)	H7A—C7—H7C	109.5
C5—C4—C4i	122.51 (19)	H7B—C7—H7C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4ii	0.82	2.03	2.770 (2)	150
O3—H3···O1iii	0.82	2.03	2.7658 (19)	150

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4i	0.82	2.03	2.770 (2)	150
O3—H3⋯O1ii	0.82	2.03	2.7658 (19)	150

Symmetry codes: (i) ; (ii) .