Bostrycin.

The title compound, C(16)H(16)O(8), is a potent nonspecific phyto-toxin. The crystal structure is the average of two tauto-mers, 5,6,7,9,10-penta-hydr-oxy-2-meth-oxy-7-methyl-1,4,5,6,7,8-hexa-hydro-anthracene-1,4-dione and 1,4,5,6,7-pentahydr-oxy-2-meth--oxy-7-methyl-5,6,7,8,9,10-hexa-hydro-anthracene-9,10-di-one. The cyclo-hexene rings in both tautomers display a half-chair conformation. An extensive O-H⋯O hydrogen-bonding network is present in the crystal structure.

Related literature

For general background, see: Charudattan & Rao (1982 ▶); van Eijk (1975 ▶). For a related structure, see: Kelly & Saha (1985 ▶).

Experimental

Crystal data

C16H16O8

M = 336.29

Monoclinic,

a = 8.280 (2) Å

b = 6.644 (2) Å

c = 13.1535 (12) Å

β = 102.12 (2)°

V = 707.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.13 mm−1

T = 293 (2) K

0.30 × 0.20 × 0.08 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.953, T max = 0.990

6151 measured reflections

1517 independent reflections

1282 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.105

S = 1.08

1517 reflections

220 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.19 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808032030/xu2453sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808032030/xu2453Isup2.hkl

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

C16H16O8	F(000) = 352
Mr = 336.29	Dx = 1.579 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2yb	Cell parameters from 5814 reflections
a = 8.280 (2) Å	θ = 6.1–54.9°
b = 6.644 (2) Å	µ = 0.13 mm−1
c = 13.1535 (12) Å	T = 293 K
β = 102.12 (2)°	Chunk, red
V = 707.5 (3) Å3	0.30 × 0.20 × 0.08 mm
Z = 2

Rigaku R-AXIS RAPID IP diffractometer	1517 independent reflections
Radiation source: fine-focus sealed tube	1282 reflections with I > 2σ(I)
graphite	Rint = 0.025
Detector resolution: 10 pixels mm-1	θmax = 26.0°, θmin = 3.2°
ω scans	h = −10→10
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −8→8
Tmin = 0.953, Tmax = 0.990	l = −16→16
6151 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0667P)2 + 0.0817P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
1517 reflections	Δρmax = 0.24 e Å−3
220 parameters	Δρmin = −0.19 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (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	Occ. (<1)
O1	0.4354 (2)	0.3424 (4)	0.34450 (13)	0.0399 (5)
H1A	0.5153	0.3341	0.3968	0.060*	0.50
O2	0.1814 (2)	0.3555 (4)	0.19361 (12)	0.0414 (5)
O3	−0.1725 (2)	0.3863 (4)	0.43528 (13)	0.0384 (5)
H3A	−0.1659	0.3844	0.4995	0.058*	0.50
O4	−0.0420 (2)	0.3933 (4)	0.63061 (13)	0.0370 (5)
H4A	−0.1226	0.4012	0.5725	0.055*	0.50
O5	0.1000 (3)	0.2810 (5)	0.82507 (17)	0.0571 (7)
H5A	0.0233	0.2963	0.7644	0.086*
O6	0.3619 (2)	0.4004 (4)	0.97960 (12)	0.0417 (5)
H6A	0.4364	0.3205	1.0303	0.063*
O7	0.5068 (2)	0.6526 (3)	0.84879 (13)	0.0336 (5)
H7A	0.5511	0.7105	0.7990	0.050*
O8	0.5671 (2)	0.3429 (4)	0.54013 (13)	0.0401 (6)
H8A	0.5559	0.3636	0.4666	0.060*	0.50
C1	0.2943 (3)	0.3552 (4)	0.37142 (18)	0.0302 (6)
C2	0.1464 (3)	0.3632 (4)	0.28875 (18)	0.0303 (6)
C3	−0.0063 (3)	0.3742 (5)	0.31216 (18)	0.0314 (6)
H3	−0.0996	0.3781	0.2587	0.038*
C4	−0.0247 (3)	0.3798 (4)	0.41735 (18)	0.0284 (5)
C5	0.1177 (3)	0.3742 (4)	0.50050 (17)	0.0263 (5)
C6	0.1023 (3)	0.3820 (4)	0.60602 (17)	0.0268 (5)
C7	0.2492 (3)	0.3761 (5)	0.68900 (17)	0.0291 (6)
C8	0.2301 (3)	0.3980 (5)	0.80142 (17)	0.0311 (6)
H8	0.2063	0.5396	0.8130	0.037*
C9	0.3863 (3)	0.3403 (4)	0.87974 (18)	0.0323 (6)
H9	0.3996	0.1938	0.8790	0.039*
C10	0.5382 (3)	0.4387 (4)	0.85300 (17)	0.0309 (6)
C11	0.5585 (3)	0.3595 (5)	0.74721 (17)	0.0319 (6)
H11A	0.6425	0.4383	0.7240	0.038*
H11B	0.5970	0.2213	0.7552	0.038*
C12	0.4022 (3)	0.3671 (4)	0.66537 (17)	0.0294 (6)
C13	0.4195 (3)	0.3563 (4)	0.55826 (18)	0.0296 (6)
C14	0.2770 (3)	0.3626 (4)	0.47627 (17)	0.0262 (5)
C15	0.0456 (3)	0.3549 (6)	0.10420 (18)	0.0435 (8)
H15A	−0.0220	0.2384	0.1068	0.065*
H15B	0.0881	0.3517	0.0417	0.065*
H15C	−0.0196	0.4743	0.1048	0.065*
C16	0.6936 (3)	0.3933 (6)	0.93488 (19)	0.0408 (7)
H16A	0.7885	0.4434	0.9117	0.061*
H16B	0.7039	0.2505	0.9453	0.061*
H16C	0.6861	0.4575	0.9991	0.061*

	U11	U22	U33	U12	U13	U23
O1	0.0294 (10)	0.0644 (15)	0.0268 (8)	0.0039 (10)	0.0076 (7)	−0.0058 (10)
O2	0.0318 (10)	0.0719 (15)	0.0203 (7)	0.0052 (11)	0.0050 (7)	−0.0025 (10)
O3	0.0233 (9)	0.0584 (13)	0.0343 (9)	0.0031 (10)	0.0082 (7)	0.0005 (10)
O4	0.0279 (10)	0.0541 (12)	0.0311 (8)	−0.0002 (10)	0.0112 (7)	−0.0016 (10)
O5	0.0513 (14)	0.0811 (19)	0.0421 (11)	−0.0192 (13)	0.0170 (10)	0.0069 (12)
O6	0.0528 (12)	0.0518 (12)	0.0226 (8)	0.0093 (11)	0.0126 (8)	0.0056 (10)
O7	0.0444 (11)	0.0318 (10)	0.0262 (8)	−0.0028 (9)	0.0112 (7)	0.0001 (8)
O8	0.0223 (9)	0.0710 (16)	0.0279 (8)	0.0015 (10)	0.0073 (7)	−0.0065 (11)
C1	0.0294 (13)	0.0370 (15)	0.0262 (11)	0.0026 (13)	0.0101 (9)	−0.0003 (12)
C2	0.0326 (14)	0.0360 (15)	0.0233 (11)	0.0014 (14)	0.0079 (9)	−0.0003 (12)
C3	0.0298 (13)	0.0360 (14)	0.0274 (11)	0.0032 (13)	0.0035 (9)	0.0003 (12)
C4	0.0249 (13)	0.0297 (13)	0.0307 (11)	0.0012 (12)	0.0064 (9)	0.0003 (12)
C5	0.0274 (13)	0.0282 (12)	0.0249 (11)	0.0006 (12)	0.0089 (9)	0.0005 (12)
C6	0.0267 (12)	0.0279 (12)	0.0278 (11)	−0.0006 (12)	0.0103 (9)	−0.0021 (12)
C7	0.0317 (13)	0.0334 (13)	0.0245 (11)	−0.0020 (13)	0.0108 (9)	−0.0003 (12)
C8	0.0335 (14)	0.0369 (14)	0.0261 (11)	−0.0011 (12)	0.0137 (10)	0.0017 (12)
C9	0.0411 (15)	0.0348 (14)	0.0232 (10)	0.0016 (13)	0.0117 (10)	0.0021 (11)
C10	0.0363 (15)	0.0338 (15)	0.0224 (12)	0.0012 (12)	0.0055 (10)	0.0004 (11)
C11	0.0283 (13)	0.0429 (16)	0.0251 (11)	0.0016 (13)	0.0067 (9)	−0.0028 (12)
C12	0.0304 (13)	0.0340 (14)	0.0248 (11)	0.0024 (13)	0.0079 (9)	−0.0028 (12)
C13	0.0270 (13)	0.0370 (15)	0.0262 (11)	0.0028 (12)	0.0087 (9)	−0.0019 (11)
C14	0.0250 (12)	0.0309 (13)	0.0230 (10)	0.0014 (12)	0.0059 (9)	−0.0019 (12)
C15	0.0381 (15)	0.068 (2)	0.0225 (11)	0.0052 (17)	0.0028 (10)	−0.0018 (15)
C16	0.0368 (15)	0.0555 (17)	0.0279 (12)	0.0023 (15)	0.0019 (10)	−0.0011 (14)

O1—C1	1.293 (3)	C5—C6	1.421 (3)
O1—H1A	0.8501	C5—C14	1.423 (3)
O2—C2	1.344 (3)	C6—C7	1.454 (3)
O2—C15	1.447 (3)	C7—C12	1.368 (4)
O3—C4	1.294 (3)	C7—C8	1.527 (3)
O3—H3A	0.8350	C8—C9	1.524 (4)
O4—C6	1.304 (3)	C8—H8	0.9800
O4—H4A	0.9046	C9—C10	1.523 (4)
O5—C8	1.415 (4)	C9—H9	0.9800
O5—H5A	0.9154	C10—C16	1.525 (3)
O6—C9	1.427 (3)	C10—C11	1.530 (3)
O6—H6A	0.9667	C11—C12	1.501 (3)
O7—C10	1.444 (3)	C11—H11A	0.9700
O7—H7A	0.9012	C11—H11B	0.9700
O8—C13	1.296 (3)	C12—C13	1.448 (3)
O8—H8A	0.9624	C13—C14	1.422 (3)
C1—C14	1.417 (3)	C15—H15A	0.9600
C1—C2	1.458 (3)	C15—H15B	0.9600
C2—C3	1.364 (4)	C15—H15C	0.9600
C3—C4	1.424 (3)	C16—H16A	0.9600
C3—H3	0.9300	C16—H16B	0.9600
C4—C5	1.431 (3)	C16—H16C	0.9600
C1—O1—H1A	112.1	C10—C9—C8	111.2 (2)
C2—O2—C15	118.3 (2)	O6—C9—H9	108.9
C4—O3—H3A	108.7	C10—C9—H9	108.9
C6—O4—H4A	110.2	C8—C9—H9	108.9
C8—O5—H5A	99.7	O7—C10—C9	106.3 (2)
C9—O6—H6A	106.8	O7—C10—C16	109.9 (2)
C10—O7—H7A	110.5	C9—C10—C16	111.6 (2)
C13—O8—H8A	106.3	O7—C10—C11	110.9 (2)
O1—C1—C14	123.4 (2)	C9—C10—C11	108.4 (2)
O1—C1—C2	117.6 (2)	C16—C10—C11	109.7 (2)
C14—C1—C2	119.0 (2)	C12—C11—C10	113.5 (2)
O2—C2—C3	127.1 (2)	C12—C11—H11A	108.9
O2—C2—C1	112.4 (2)	C10—C11—H11A	108.9
C3—C2—C1	120.4 (2)	C12—C11—H11B	108.9
C2—C3—C4	120.9 (2)	C10—C11—H11B	108.9
C2—C3—H3	119.5	H11A—C11—H11B	107.7
C4—C3—H3	119.5	C7—C12—C13	120.6 (2)
O3—C4—C3	118.4 (2)	C7—C12—C11	122.6 (2)
O3—C4—C5	121.4 (2)	C13—C12—C11	116.7 (2)
C3—C4—C5	120.2 (2)	O8—C13—C14	121.8 (2)
C6—C5—C14	119.9 (2)	O8—C13—C12	118.2 (2)
C6—C5—C4	121.1 (2)	C14—C13—C12	120.1 (2)
C14—C5—C4	119.0 (2)	C1—C14—C13	120.0 (2)
O4—C6—C5	121.3 (2)	C1—C14—C5	120.5 (2)
O4—C6—C7	118.7 (2)	C13—C14—C5	119.5 (2)
C5—C6—C7	120.0 (2)	O2—C15—H15A	109.5
C12—C7—C6	119.9 (2)	O2—C15—H15B	109.5
C12—C7—C8	120.9 (2)	H15A—C15—H15B	109.5
C6—C7—C8	119.0 (2)	O2—C15—H15C	109.5
O5—C8—C9	106.9 (2)	H15A—C15—H15C	109.5
O5—C8—C7	113.5 (2)	H15B—C15—H15C	109.5
C9—C8—C7	112.6 (2)	C10—C16—H16A	109.5
O5—C8—H8	107.8	C10—C16—H16B	109.5
C9—C8—H8	107.8	H16A—C16—H16B	109.5
C7—C8—H8	107.8	C10—C16—H16C	109.5
O6—C9—C10	112.1 (2)	H16A—C16—H16C	109.5
O6—C9—C8	106.7 (2)	H16B—C16—H16C	109.5

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3i	0.85	2.55	3.229 (3)	137
O3—H3A···O8ii	0.84	2.40	2.808 (3)	111
O4—H4A···O8ii	0.90	2.54	3.223 (3)	132
O5—H5A···O4	0.92	1.85	2.687 (3)	152
O6—H6A···O7iii	0.97	1.92	2.821 (3)	154
O7—H7A···O1iv	0.90	2.11	2.966 (3)	159
O7—H7A···O2iv	0.90	2.40	3.066 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3i	0.85	2.55	3.229 (3)	137
O3—H3A⋯O8ii	0.84	2.40	2.808 (3)	111
O4—H4A⋯O8ii	0.90	2.54	3.223 (3)	132
O5—H5A⋯O4	0.92	1.85	2.687 (3)	152
O6—H6A⋯O7iii	0.97	1.92	2.821 (3)	154
O7—H7A⋯O1iv	0.90	2.11	2.966 (3)	159
O7—H7A⋯O2iv	0.90	2.40	3.066 (3)	131

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