9β-Hy-droxy-1β,10α-ep-oxy-parthenolide.

The title compound, C(15)H(20)O(5) (systematic name: 5-hydroxy-1a,4a-dimethyl-7-methyleneperhydrodioxireno[5,6:9,10]cyclo-deca[1,2-b]furan-8-one), was obtained by the reaction of 3-chloro-perbenzoic acid with 9β-hy-droxy-parthenolide. The five-membered ring adopts a twist conformation, whereas the ten-membered ring displays an approximate chair-chair conformation. In the crystal structure, mol-ecules are linked into chains propagating along the b axis by inter-molecular O-H⋯O hydrogen bonds.

Related literature

For background to the medicinal uses of the plant Anvillea radiata, see: Abdel Sattar et al. (1996 ▶); Bellakhdar (1997 ▶); El Hassany et al. (2004 ▶); Qureshi et al. (1990 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For conformations of ten-membered rings, see: Castaneda-Acosta et al. (1997 ▶); Watson & Zabel (1982 ▶).

Experimental

Crystal data

C15H20O5

M = 280.31

Monoclinic,

a = 9.2295 (3) Å

b = 9.5431 (3) Å

c = 9.3787 (3) Å

β = 118.662 (2)°

V = 724.84 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 298 K

0.27 × 0.18 × 0.12 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

8090 measured reflections

1617 independent reflections

1378 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.05

1617 reflections

184 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810033404/ci5157sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033404/ci5157Isup2.hkl

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

C15H20O5	F(000) = 300
Mr = 280.31	Dx = 1.284 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 8090 reflections
a = 9.2295 (3) Å	θ = 2.5–26.5°
b = 9.5431 (3) Å	µ = 0.10 mm−1
c = 9.3787 (3) Å	T = 298 K
β = 118.662 (2)°	Prism, colourless
V = 724.84 (4) Å3	0.27 × 0.18 × 0.12 mm
Z = 2

Bruker X8 APEXII CCD area-detector diffractometer	1378 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 26.7°, θmin = 2.5°
φ and ω scans	h = −11→11
8090 measured reflections	k = −10→12
1617 independent reflections	l = −11→11

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0541P)2 + 0.0327P] where P = (Fo2 + 2Fc2)/3
1617 reflections	(Δ/σ)max = 0.001
184 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.13 e Å−3

	x	y	z	Uiso*/Ueq
C1	−0.1569 (3)	0.2114 (3)	0.0240 (3)	0.0445 (5)
H1	−0.0953	0.2863	0.0055	0.053*
C2	−0.3412 (3)	0.2235 (3)	−0.0757 (3)	0.0567 (7)
H2A	−0.3919	0.1709	−0.0227	0.068*
H2B	−0.3757	0.1811	−0.1811	0.068*
C3	−0.4043 (3)	0.3738 (4)	−0.1004 (3)	0.0638 (8)
H3A	−0.3743	0.4211	−0.1741	0.077*
H3B	−0.5238	0.3729	−0.1505	0.077*
C4	−0.3354 (3)	0.4546 (3)	0.0564 (3)	0.0522 (6)
C5	−0.1856 (3)	0.5389 (3)	0.0973 (3)	0.0493 (6)
H5	−0.1470	0.5325	0.0167	0.059*
C6	−0.0511 (2)	0.5623 (2)	0.2665 (3)	0.0421 (5)
H6	−0.0915	0.5477	0.3448	0.051*
C7	0.0972 (3)	0.4660 (2)	0.3050 (3)	0.0367 (5)
H7	0.0907	0.4403	0.2009	0.044*
C8	0.1049 (3)	0.3287 (2)	0.3942 (3)	0.0423 (5)
H8A	0.2046	0.3294	0.4986	0.051*
H8B	0.0116	0.3261	0.4149	0.051*
C9	0.1036 (3)	0.1953 (2)	0.3041 (3)	0.0395 (5)
H9	0.1641	0.2126	0.2439	0.047*
C10	−0.0689 (3)	0.1455 (2)	0.1862 (3)	0.0407 (5)
C11	0.2419 (3)	0.5625 (2)	0.3892 (3)	0.0399 (5)
C12	0.1773 (3)	0.7075 (2)	0.3533 (3)	0.0465 (5)
C13	0.3997 (3)	0.5360 (3)	0.4776 (3)	0.0601 (7)
H13A	0.4749	0.6094	0.5198	0.072*
H13B	0.4367	0.4438	0.4980	0.072*
C14	−0.1584 (3)	0.0708 (3)	0.2633 (3)	0.0589 (7)
H14A	−0.1411	0.1202	0.3593	0.088*
H14B	−0.1164	−0.0229	0.2917	0.088*
H14C	−0.2744	0.0675	0.1877	0.088*
C15	−0.3799 (3)	0.4050 (3)	0.1816 (3)	0.0599 (7)
H15A	−0.3367	0.4691	0.2715	0.090*
H15B	−0.3336	0.3137	0.2190	0.090*
H15C	−0.4979	0.4004	0.1347	0.090*
O1	−0.3421 (2)	0.6072 (2)	0.0388 (3)	0.0650 (5)
O2	0.1910 (2)	0.09367 (17)	0.4267 (2)	0.0569 (5)
H2	0.1973	0.0204	0.3843	0.085*
O3	0.0115 (2)	0.70565 (16)	0.2779 (2)	0.0539 (4)
O4	0.2528 (2)	0.81591 (19)	0.3811 (2)	0.0653 (5)
O5	−0.0845 (2)	0.07350 (19)	0.0434 (2)	0.0549 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0426 (11)	0.0524 (14)	0.0442 (11)	−0.0061 (10)	0.0254 (9)	−0.0082 (11)
C2	0.0443 (13)	0.077 (2)	0.0458 (13)	−0.0123 (12)	0.0194 (10)	−0.0122 (13)
C3	0.0351 (12)	0.091 (2)	0.0544 (15)	0.0047 (12)	0.0123 (11)	0.0073 (14)
C4	0.0341 (11)	0.0619 (16)	0.0599 (15)	0.0111 (10)	0.0221 (10)	0.0078 (12)
C5	0.0391 (11)	0.0543 (14)	0.0561 (13)	0.0127 (10)	0.0241 (10)	0.0159 (11)
C6	0.0454 (11)	0.0330 (12)	0.0557 (13)	0.0072 (9)	0.0306 (10)	0.0073 (10)
C7	0.0431 (12)	0.0284 (10)	0.0398 (11)	0.0044 (8)	0.0210 (9)	0.0030 (8)
C8	0.0550 (12)	0.0300 (11)	0.0416 (11)	0.0007 (10)	0.0228 (9)	0.0020 (9)
C9	0.0446 (11)	0.0293 (10)	0.0465 (12)	0.0023 (9)	0.0232 (10)	0.0002 (9)
C10	0.0484 (12)	0.0347 (11)	0.0488 (12)	−0.0043 (9)	0.0311 (10)	−0.0063 (9)
C11	0.0450 (11)	0.0321 (11)	0.0442 (11)	0.0009 (9)	0.0227 (9)	0.0015 (9)
C12	0.0569 (13)	0.0331 (12)	0.0544 (13)	0.0020 (11)	0.0306 (11)	−0.0006 (11)
C13	0.0461 (13)	0.0519 (15)	0.0699 (16)	0.0010 (11)	0.0178 (11)	0.0071 (13)
C14	0.0654 (15)	0.0529 (16)	0.0695 (16)	−0.0123 (13)	0.0413 (13)	0.0045 (13)
C15	0.0536 (14)	0.0636 (17)	0.0754 (18)	0.0038 (13)	0.0413 (13)	0.0003 (13)
O1	0.0441 (10)	0.0637 (13)	0.0835 (12)	0.0202 (8)	0.0276 (9)	0.0214 (10)
O2	0.0673 (11)	0.0297 (8)	0.0630 (10)	0.0118 (8)	0.0226 (9)	0.0057 (8)
O3	0.0574 (10)	0.0299 (8)	0.0780 (11)	0.0121 (8)	0.0355 (9)	0.0071 (9)
O4	0.0786 (13)	0.0307 (8)	0.0896 (13)	−0.0083 (8)	0.0429 (10)	−0.0048 (9)
O5	0.0596 (9)	0.0517 (10)	0.0604 (10)	−0.0073 (8)	0.0342 (8)	−0.0212 (8)

C1—O5	1.447 (3)	C8—C9	1.525 (3)
C1—C10	1.477 (3)	C8—H8A	0.97
C1—C2	1.502 (3)	C8—H8B	0.97
C1—H1	0.98	C9—O2	1.422 (3)
C2—C3	1.524 (4)	C9—C10	1.515 (3)
C2—H2A	0.97	C9—H9	0.98
C2—H2B	0.97	C10—O5	1.449 (3)
C3—C4	1.505 (4)	C10—C14	1.512 (3)
C3—H3A	0.97	C11—C13	1.310 (3)
C3—H3B	0.97	C11—C12	1.480 (3)
C4—O1	1.463 (3)	C12—O4	1.204 (3)
C4—C5	1.482 (4)	C12—O3	1.343 (3)
C4—C15	1.495 (4)	C13—H13A	0.93
C5—O1	1.432 (3)	C13—H13B	0.93
C5—C6	1.490 (3)	C14—H14A	0.96
C5—H5	0.98	C14—H14B	0.96
C6—O3	1.469 (3)	C14—H14C	0.96
C6—C7	1.541 (3)	C15—H15A	0.96
C6—H6	0.98	C15—H15B	0.96
C7—C11	1.498 (3)	C15—H15C	0.96
C7—C8	1.537 (3)	O2—H2	0.82
C7—H7	0.98
O5—C1—C10	59.41 (15)	C9—C8—H8A	108.5
O5—C1—C2	117.7 (2)	C7—C8—H8A	108.5
C10—C1—C2	124.9 (2)	C9—C8—H8B	108.5
O5—C1—H1	114.4	C7—C8—H8B	108.5
C10—C1—H1	114.4	H8A—C8—H8B	107.5
C2—C1—H1	114.4	O2—C9—C10	111.51 (18)
C1—C2—C3	113.8 (2)	O2—C9—C8	105.69 (16)
C1—C2—H2A	108.8	C10—C9—C8	113.10 (17)
C3—C2—H2A	108.8	O2—C9—H9	108.8
C1—C2—H2B	108.8	C10—C9—H9	108.8
C3—C2—H2B	108.8	C8—C9—H9	108.8
H2A—C2—H2B	107.7	O5—C10—C1	59.26 (15)
C4—C3—C2	112.5 (2)	O5—C10—C14	112.5 (2)
C4—C3—H3A	109.1	C1—C10—C14	122.4 (2)
C2—C3—H3A	109.1	O5—C10—C9	115.25 (17)
C4—C3—H3B	109.1	C1—C10—C9	119.00 (18)
C2—C3—H3B	109.1	C14—C10—C9	115.0 (2)
H3A—C3—H3B	107.8	C13—C11—C12	121.9 (2)
O1—C4—C5	58.19 (16)	C13—C11—C7	130.9 (2)
O1—C4—C15	113.1 (2)	C12—C11—C7	107.19 (18)
C5—C4—C15	122.8 (2)	O4—C12—O3	121.4 (2)
O1—C4—C3	115.1 (2)	O4—C12—C11	128.7 (2)
C5—C4—C3	115.8 (2)	O3—C12—C11	109.87 (19)
C15—C4—C3	117.3 (2)	C11—C13—H13A	120.0
O1—C5—C4	60.23 (15)	C11—C13—H13B	120.0
O1—C5—C6	120.8 (2)	H13A—C13—H13B	120.0
C4—C5—C6	123.7 (2)	C10—C14—H14A	109.5
O1—C5—H5	113.9	C10—C14—H14B	109.5
C4—C5—H5	113.9	H14A—C14—H14B	109.5
C6—C5—H5	113.9	C10—C14—H14C	109.5
O3—C6—C5	108.32 (18)	H14A—C14—H14C	109.5
O3—C6—C7	105.30 (16)	H14B—C14—H14C	109.5
C5—C6—C7	110.70 (18)	C4—C15—H15A	109.5
O3—C6—H6	110.8	C4—C15—H15B	109.5
C5—C6—H6	110.8	H15A—C15—H15B	109.5
C7—C6—H6	110.8	C4—C15—H15C	109.5
C11—C7—C8	116.15 (18)	H15A—C15—H15C	109.5
C11—C7—C6	102.94 (17)	H15B—C15—H15C	109.5
C8—C7—C6	116.07 (17)	C5—O1—C4	61.57 (16)
C11—C7—H7	107.0	C9—O2—H2	109.5
C8—C7—H7	107.0	C12—O3—C6	111.09 (16)
C6—C7—H7	107.0	C1—O5—C10	61.33 (14)
C9—C8—C7	115.12 (17)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4i	0.82	2.02	2.787 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O4i	0.82	2.02	2.787 (3)	155

Symmetry code: (i) .