5α-Hy-droxy-eudesm-4(15),11(13)-dien-8β,12-olide.

The title compound, C(15)H(20)O(3), a sesquiterpene lactone, was isolated from the aerial parts of Carpesium minus Hemsl. (Compositae). The mol-ecule is composed of three rings, with the two cyclo-hexane rings in chair conformations and the cyclo-pentane ring adopting a twist conformation. The A/B ring junction is trans-fused. The absolute configuration shown has been arbitrarily assigned. In the crystal, mol-ecules are linked into [100] chains by O-H⋯O hydrogen bonds.

Related literature

For the isolation and biological activity of the title compound, see: Lee et al. (2002 ▶); Yang et al. (2002 ▶); Li et al. (2011 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C15H20O3

M = 248.31

Monoclinic,

a = 7.893 (2) Å

b = 7.034 (2) Å

c = 12.166 (4) Å

β = 101.154 (3)°

V = 662.7 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 296 K

0.23 × 0.20 × 0.19 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2006 ▶) T min = 0.981, T max = 0.984

3673 measured reflections

1323 independent reflections

1159 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.084

S = 1.08

1323 reflections

165 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.17 e Å−3

Data collection: APEX2 (Bruker, 2006 ▶); cell refinement: SAINT (Bruker, 2006 ▶); data reduction: SAINT; 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 datablock(s) I, global. DOI: 10.1107/S1600536812012470/rn2102sup1.cif

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

C15H20O3	F(000) = 268
Mr = 248.31	Dx = 1.244 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 7.893 (2) Å	Cell parameters from 1583 reflections
b = 7.034 (2) Å	θ = 2.9–23.8°
c = 12.166 (4) Å	µ = 0.09 mm−1
β = 101.154 (3)°	T = 296 K
V = 662.7 (3) Å3	Block, colorless
Z = 2	0.23 × 0.20 × 0.19 mm

Bruker APEXII CCD diffractometer	1323 independent reflections
Radiation source: fine-focus sealed tube	1159 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
φ and ω scans	θmax = 25.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2006)	h = −9→9
Tmin = 0.981, Tmax = 0.984	k = −8→7
3673 measured reflections	l = −13→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.084	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.046P)2 + 0.026P] where P = (Fo2 + 2Fc2)/3
1323 reflections	(Δ/σ)max < 0.001
165 parameters	Δρmax = 0.12 e Å−3
1 restraint	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
C1	0.5831 (3)	0.5040 (4)	0.2805 (2)	0.0451 (6)
H1	0.5843	0.6432	0.2844	0.054*
C2	0.6238 (3)	0.4471 (4)	0.1686 (2)	0.0462 (6)
H2A	0.7088	0.5353	0.1504	0.055*
H2B	0.5197	0.4618	0.1120	0.055*
C3	0.6920 (3)	0.2446 (4)	0.16056 (19)	0.0404 (6)
C4	0.7625 (4)	0.2265 (4)	0.0514 (2)	0.0534 (7)
H4A	0.6677	0.2421	−0.0118	0.064*
H4B	0.8442	0.3285	0.0486	0.064*
C5	0.8506 (4)	0.0380 (5)	0.0400 (2)	0.0663 (9)
H5A	0.8998	0.0396	−0.0272	0.080*
H5B	0.7660	−0.0635	0.0325	0.080*
C6	0.9931 (4)	−0.0002 (5)	0.1417 (2)	0.0619 (8)
H6A	1.0384	−0.1275	0.1367	0.074*
H6B	1.0868	0.0893	0.1425	0.074*
C7	0.9243 (3)	0.0189 (4)	0.2486 (2)	0.0428 (6)
C8	0.8428 (3)	0.2111 (3)	0.26178 (18)	0.0370 (5)
C9	0.7793 (3)	0.2326 (3)	0.37155 (18)	0.0364 (5)
H9A	0.8753	0.2109	0.4332	0.044*
H9B	0.6931	0.1357	0.3752	0.044*
C10	0.7006 (3)	0.4286 (3)	0.38653 (18)	0.0391 (5)
H10	0.7921	0.5208	0.4142	0.047*
C11	0.5786 (3)	0.4143 (3)	0.46605 (19)	0.0397 (5)
C12	0.4025 (3)	0.4029 (3)	0.3975 (2)	0.0439 (6)
C13	0.5451 (3)	0.0994 (4)	0.1587 (2)	0.0491 (6)
H13A	0.4607	0.1147	0.0910	0.074*
H13B	0.4917	0.1202	0.2222	0.074*
H13C	0.5915	−0.0271	0.1618	0.074*
C14	0.9291 (3)	−0.1238 (4)	0.3199 (2)	0.0514 (6)
H14A	0.9759	−0.2401	0.3049	0.062*
H14B	0.8857	−0.1079	0.3852	0.062*
C15	0.6070 (3)	0.4053 (4)	0.5758 (2)	0.0516 (7)
H15A	0.5149	0.3913	0.6127	0.062*
H15B	0.7192	0.4128	0.6168	0.062*
O1	0.9648 (2)	0.3595 (3)	0.25349 (15)	0.0503 (5)
H1A	1.0515	0.3445	0.3021	0.075*
O2	0.40859 (19)	0.4391 (3)	0.28997 (13)	0.0530 (5)
O3	0.2681 (2)	0.3667 (3)	0.42676 (14)	0.0585 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0446 (14)	0.0397 (13)	0.0508 (14)	0.0042 (11)	0.0082 (11)	0.0056 (12)
C2	0.0434 (13)	0.0513 (15)	0.0420 (13)	0.0031 (12)	0.0038 (10)	0.0127 (12)
C3	0.0365 (12)	0.0485 (15)	0.0358 (12)	0.0004 (11)	0.0058 (10)	0.0046 (11)
C4	0.0549 (15)	0.0681 (19)	0.0381 (13)	0.0003 (15)	0.0112 (11)	0.0055 (13)
C5	0.0695 (19)	0.083 (2)	0.0496 (16)	0.0125 (18)	0.0210 (14)	−0.0051 (15)
C6	0.0571 (17)	0.072 (2)	0.0608 (17)	0.0137 (15)	0.0213 (14)	−0.0028 (15)
C7	0.0332 (12)	0.0468 (14)	0.0473 (14)	0.0009 (11)	0.0050 (10)	−0.0027 (12)
C8	0.0299 (11)	0.0393 (12)	0.0405 (12)	−0.0064 (10)	0.0037 (9)	0.0032 (10)
C9	0.0331 (12)	0.0388 (13)	0.0346 (12)	−0.0009 (10)	−0.0001 (9)	0.0001 (10)
C10	0.0360 (12)	0.0373 (13)	0.0421 (12)	−0.0046 (11)	0.0030 (9)	−0.0010 (11)
C11	0.0380 (12)	0.0347 (12)	0.0463 (13)	−0.0018 (11)	0.0077 (10)	−0.0058 (10)
C12	0.0395 (13)	0.0425 (14)	0.0491 (14)	0.0017 (11)	0.0076 (10)	−0.0060 (11)
C13	0.0422 (14)	0.0570 (16)	0.0447 (14)	−0.0085 (12)	0.0003 (11)	−0.0044 (12)
C14	0.0465 (14)	0.0438 (15)	0.0634 (16)	0.0054 (12)	0.0096 (12)	−0.0006 (13)
C15	0.0537 (15)	0.0541 (16)	0.0471 (15)	0.0042 (13)	0.0099 (11)	−0.0043 (12)
O1	0.0357 (9)	0.0532 (11)	0.0608 (11)	−0.0118 (8)	0.0062 (7)	0.0067 (9)
O2	0.0357 (9)	0.0746 (13)	0.0470 (10)	0.0067 (9)	0.0036 (7)	0.0005 (9)
O3	0.0364 (9)	0.0772 (13)	0.0632 (11)	−0.0042 (9)	0.0130 (8)	−0.0094 (10)

C1—O2	1.476 (3)	C7—C8	1.519 (3)
C1—C2	1.512 (3)	C8—O1	1.437 (3)
C1—C10	1.531 (3)	C8—C9	1.522 (3)
C1—H1	0.9800	C9—C10	1.538 (3)
C2—C3	1.533 (4)	C9—H9A	0.9700
C2—H2A	0.9700	C9—H9B	0.9700
C2—H2B	0.9700	C10—C11	1.495 (3)
C3—C4	1.541 (3)	C10—H10	0.9800
C3—C13	1.542 (3)	C11—C15	1.312 (3)
C3—C8	1.556 (3)	C11—C12	1.478 (3)
C4—C5	1.516 (4)	C12—O3	1.210 (3)
C4—H4A	0.9700	C12—O2	1.342 (3)
C4—H4B	0.9700	C13—H13A	0.9600
C5—C6	1.526 (4)	C13—H13B	0.9600
C5—H5A	0.9700	C13—H13C	0.9600
C5—H5B	0.9700	C14—H14A	0.9300
C6—C7	1.509 (3)	C14—H14B	0.9300
C6—H6A	0.9700	C15—H15A	0.9300
C6—H6B	0.9700	C15—H15B	0.9300
C7—C14	1.323 (4)	O1—H1A	0.8200
O2—C1—C2	110.7 (2)	O1—C8—C7	109.61 (18)
O2—C1—C10	104.44 (17)	O1—C8—C9	109.18 (19)
C2—C1—C10	117.9 (2)	C7—C8—C9	113.54 (19)
O2—C1—H1	107.8	O1—C8—C3	104.78 (17)
C2—C1—H1	107.8	C7—C8—C3	109.00 (19)
C10—C1—H1	107.8	C9—C8—C3	110.37 (17)
C1—C2—C3	116.2 (2)	C8—C9—C10	113.71 (18)
C1—C2—H2A	108.2	C8—C9—H9A	108.8
C3—C2—H2A	108.2	C10—C9—H9A	108.8
C1—C2—H2B	108.2	C8—C9—H9B	108.8
C3—C2—H2B	108.2	C10—C9—H9B	108.8
H2A—C2—H2B	107.4	H9A—C9—H9B	107.7
C2—C3—C4	108.73 (19)	C11—C10—C1	101.97 (17)
C2—C3—C13	110.1 (2)	C11—C10—C9	109.97 (19)
C4—C3—C13	109.2 (2)	C1—C10—C9	113.80 (19)
C2—C3—C8	108.32 (19)	C11—C10—H10	110.3
C4—C3—C8	108.73 (18)	C1—C10—H10	110.3
C13—C3—C8	111.67 (18)	C9—C10—H10	110.3
C5—C4—C3	113.5 (2)	C15—C11—C12	121.9 (2)
C5—C4—H4A	108.9	C15—C11—C10	131.1 (2)
C3—C4—H4A	108.9	C12—C11—C10	106.96 (19)
C5—C4—H4B	108.9	O3—C12—O2	121.7 (2)
C3—C4—H4B	108.9	O3—C12—C11	128.9 (2)
H4A—C4—H4B	107.7	O2—C12—C11	109.43 (19)
C4—C5—C6	111.1 (3)	C3—C13—H13A	109.5
C4—C5—H5A	109.4	C3—C13—H13B	109.5
C6—C5—H5A	109.4	H13A—C13—H13B	109.5
C4—C5—H5B	109.4	C3—C13—H13C	109.5
C6—C5—H5B	109.4	H13A—C13—H13C	109.5
H5A—C5—H5B	108.0	H13B—C13—H13C	109.5
C7—C6—C5	110.5 (2)	C7—C14—H14A	120.0
C7—C6—H6A	109.5	C7—C14—H14B	120.0
C5—C6—H6A	109.5	H14A—C14—H14B	120.0
C7—C6—H6B	109.5	C11—C15—H15A	120.0
C5—C6—H6B	109.5	C11—C15—H15B	120.0
H6A—C6—H6B	108.1	H15A—C15—H15B	120.0
C14—C7—C6	121.9 (2)	C8—O1—H1A	109.5
C14—C7—C8	124.4 (2)	C12—O2—C1	110.15 (17)
C6—C7—C8	113.6 (2)
O2—C1—C2—C3	−83.6 (3)	C2—C3—C8—C9	60.6 (2)
C10—C1—C2—C3	36.5 (3)	C4—C3—C8—C9	178.6 (2)
C1—C2—C3—C4	−168.0 (2)	C13—C3—C8—C9	−60.9 (2)
C1—C2—C3—C13	72.4 (3)	O1—C8—C9—C10	56.0 (2)
C1—C2—C3—C8	−49.9 (3)	C7—C8—C9—C10	178.61 (18)
C2—C3—C4—C5	174.0 (2)	C3—C8—C9—C10	−58.7 (2)
C13—C3—C4—C5	−65.8 (3)	O2—C1—C10—C11	−26.1 (2)
C8—C3—C4—C5	56.2 (3)	C2—C1—C10—C11	−149.3 (2)
C3—C4—C5—C6	−54.6 (3)	O2—C1—C10—C9	92.3 (2)
C4—C5—C6—C7	52.6 (3)	C2—C1—C10—C9	−31.0 (3)
C5—C6—C7—C14	120.5 (3)	C8—C9—C10—C11	156.08 (18)
C5—C6—C7—C8	−56.6 (3)	C8—C9—C10—C1	42.4 (2)
C14—C7—C8—O1	127.5 (3)	C1—C10—C11—C15	−160.4 (3)
C6—C7—C8—O1	−55.5 (3)	C9—C10—C11—C15	78.5 (3)
C14—C7—C8—C9	5.1 (3)	C1—C10—C11—C12	22.0 (2)
C6—C7—C8—C9	−177.9 (2)	C9—C10—C11—C12	−99.1 (2)
C14—C7—C8—C3	−118.4 (3)	C15—C11—C12—O3	−7.9 (4)
C6—C7—C8—C3	58.6 (2)	C10—C11—C12—O3	170.0 (3)
C2—C3—C8—O1	−56.8 (2)	C15—C11—C12—O2	172.5 (2)
C4—C3—C8—O1	61.2 (2)	C10—C11—C12—O2	−9.7 (3)
C13—C3—C8—O1	−178.3 (2)	O3—C12—O2—C1	172.3 (2)
C2—C3—C8—C7	−174.07 (19)	C11—C12—O2—C1	−8.1 (3)
C4—C3—C8—C7	−56.1 (2)	C2—C1—O2—C12	149.8 (2)
C13—C3—C8—C7	64.5 (2)	C10—C1—O2—C12	22.0 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O3i	0.82	2.06	2.868 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O3i	0.82	2.06	2.868 (2)	168

Symmetry code: (i) .