Crystal structure of pseudoguainolide.

The lactone ring in the title mol-ecule, C15H22O3 (systematic name: 3,4a,8-tri-methyl-dodeca-hydro-azuleno[6,5-b]furan-2,5-dione), assumes an envelope conformation with the methine C atom adjacent to the the methine C atom carrying the methyl substituent being the flap atom. The other five-membered ring adopts a twisted conformation with the twist being about the methine-methyl-ene C-C bond. The seven-membered ring is based on a twisted boat conformation. No specific inter-actions are noted in the the crystal packing.

Related literature

For background to inula graveolens, see: Chiappini & Fardella (1980 ▸); Rustaiyan et al. (1987 ▸). For related structures, see: Herz et al. (1982 ▸); Schmidt et al. (1996 ▸); Wu et al. (2012 ▸); Billodeaux et al. (2014 ▸).

Experimental

Crystal data

C15H22O3

M = 250.33

Orthorhombic,

a = 7.4320 (3) Å

b = 11.9278 (3) Å

c = 15.3152 (6) Å

V = 1357.65 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 150 K

0.20 × 0.20 × 0.04 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▸) T min = 0.984, T max = 0.997

9382 measured reflections

3098 independent reflections

2533 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.107

S = 1.08

3098 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.16 e Å−3

Data collection: COLLECT (Nonius, 2000 ▸); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▸); data reduction: DENZO (Otwinowski & Minor, 1997 ▸) and SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1999 ▸); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▸); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▸); software used to prepare material for publication: WinGX (Farrugia, 2012 ▸).

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S2056989015002510/tk5358sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S2056989015002510/tk5358Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S2056989015002510/tk5358Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S2056989015002510/tk5358fig1.tif

A mol­ecule showing atom labels and 50% probability displacement ellipsoids for non-H atoms.

CCDC reference: 1047797

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H22O3	Dx = 1.225 Mg m−3
Mr = 250.33	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P212121	Cell parameters from 3098 reflections
a = 7.4320 (3) Å	θ = 3.1–27.5°
b = 11.9278 (3) Å	µ = 0.08 mm−1
c = 15.3152 (6) Å	T = 150 K
V = 1357.65 (8) Å3	Plate, colourless
Z = 4	0.20 × 0.20 × 0.04 mm
F(000) = 544

Nonius KappaCCD diffractometer	3098 independent reflections
Radiation source: fine-focus sealed tube	2533 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.041
CCD slices, ω and φ scans	θmax = 27.5°, θmin = 3.1°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −9→9
Tmin = 0.984, Tmax = 0.997	k = −15→15
9382 measured reflections	l = −19→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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0453P)2 + 0.2031P] where P = (Fo2 + 2Fc2)/3
3098 reflections	(Δ/σ)max < 0.001
166 parameters	Δρmax = 0.15 e Å−3
0 restraints	Δρmin = −0.16 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.8136 (2)	0.24699 (16)	0.52812 (12)	0.0383 (4)
C2	0.8423 (3)	0.16380 (15)	0.45546 (12)	0.0407 (4)
H2	0.9722	0.1503	0.4522	0.049*
C3	0.7918 (2)	0.22980 (13)	0.37360 (11)	0.0318 (4)
H3	0.6620	0.2220	0.3642	0.038*
C4	0.8307 (2)	0.35109 (14)	0.40005 (11)	0.0338 (4)
H4	0.9552	0.3703	0.3852	0.041*
C5	0.8884 (2)	0.19024 (14)	0.29170 (12)	0.0346 (4)
H5A	0.8386	0.1183	0.2748	0.041*
H5B	1.0142	0.1785	0.3060	0.041*
C6	0.8781 (2)	0.26974 (15)	0.21218 (12)	0.0371 (4)
C7	0.7099 (3)	0.34762 (15)	0.20872 (12)	0.0388 (4)
H7	0.6065	0.3039	0.2292	0.047*
C8	0.7176 (3)	0.45618 (14)	0.26350 (13)	0.0429 (5)
H8	0.8326	0.4932	0.2513	0.052*
C9	0.7050 (3)	0.43722 (14)	0.36244 (12)	0.0396 (4)
H9A	0.7276	0.5081	0.3914	0.048*
H9B	0.5827	0.4152	0.3763	0.048*
C10	0.8618 (3)	0.20169 (18)	0.12824 (14)	0.0495 (5)
C11	0.7283 (4)	0.25562 (19)	0.06728 (14)	0.0630 (6)
H11A	0.6211	0.2099	0.0617	0.076*
H11B	0.7805	0.2665	0.0098	0.076*
C12	0.6842 (3)	0.36830 (18)	0.10993 (14)	0.0583 (6)
H12A	0.5613	0.3905	0.0973	0.070*
H12B	0.7651	0.4264	0.0893	0.070*
C13	0.7564 (3)	0.05319 (14)	0.47094 (13)	0.0453 (5)
H13A	0.6282	0.0623	0.4737	0.068*
H13B	0.7992	0.0226	0.5251	0.068*
H13C	0.7864	0.0032	0.4240	0.068*
C14	1.0567 (3)	0.33493 (19)	0.20250 (15)	0.0519 (5)
H14A	1.0488	0.3846	0.1533	0.078*
H14B	1.1536	0.2830	0.1937	0.078*
H14C	1.0786	0.3777	0.2545	0.078*
C15	0.5664 (3)	0.53701 (18)	0.23775 (17)	0.0650 (7)
H15A	0.5670	0.6004	0.2764	0.098*
H15B	0.4526	0.4992	0.2419	0.098*
H15C	0.5847	0.5620	0.1788	0.098*
O1	0.79726 (18)	0.22938 (12)	0.60507 (9)	0.0478 (3)
O2	0.80792 (16)	0.35200 (10)	0.49559 (7)	0.0390 (3)
O3	0.9465 (2)	0.11791 (15)	0.11224 (11)	0.0721 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0265 (8)	0.0451 (10)	0.0433 (11)	−0.0014 (8)	−0.0003 (8)	0.0008 (8)
C2	0.0416 (10)	0.0404 (9)	0.0400 (10)	−0.0014 (8)	0.0015 (8)	0.0040 (8)
C3	0.0265 (8)	0.0298 (8)	0.0392 (9)	−0.0018 (7)	0.0004 (7)	0.0008 (7)
C4	0.0296 (9)	0.0335 (8)	0.0384 (9)	−0.0040 (7)	0.0040 (7)	−0.0020 (7)
C5	0.0314 (9)	0.0331 (9)	0.0393 (10)	0.0025 (7)	−0.0013 (8)	−0.0011 (7)
C6	0.0344 (9)	0.0381 (9)	0.0387 (10)	−0.0011 (8)	0.0020 (8)	0.0015 (8)
C7	0.0381 (9)	0.0357 (8)	0.0426 (10)	0.0007 (8)	−0.0058 (8)	0.0050 (8)
C8	0.0453 (11)	0.0301 (8)	0.0534 (12)	0.0008 (9)	0.0005 (9)	0.0064 (8)
C9	0.0373 (10)	0.0303 (8)	0.0512 (11)	−0.0012 (8)	0.0023 (9)	−0.0031 (7)
C10	0.0526 (12)	0.0532 (12)	0.0426 (12)	0.0015 (10)	−0.0019 (9)	−0.0027 (9)
C11	0.0807 (17)	0.0660 (14)	0.0424 (12)	0.0121 (14)	−0.0134 (12)	−0.0037 (10)
C12	0.0731 (15)	0.0544 (12)	0.0472 (12)	0.0092 (12)	−0.0115 (12)	0.0079 (9)
C13	0.0473 (11)	0.0383 (10)	0.0502 (12)	0.0076 (9)	0.0064 (9)	0.0056 (8)
C14	0.0441 (11)	0.0595 (12)	0.0522 (13)	−0.0096 (10)	0.0101 (10)	0.0073 (10)
C15	0.0772 (17)	0.0419 (11)	0.0761 (17)	0.0178 (12)	−0.0123 (14)	0.0068 (11)
O1	0.0432 (8)	0.0636 (8)	0.0367 (8)	−0.0003 (7)	0.0028 (6)	0.0023 (6)
O2	0.0380 (7)	0.0401 (7)	0.0388 (7)	−0.0038 (6)	0.0016 (6)	−0.0055 (5)
O3	0.0840 (12)	0.0763 (11)	0.0560 (10)	0.0307 (10)	−0.0134 (9)	−0.0248 (9)

C1—O1	1.203 (2)	C8—C15	1.532 (3)
C1—O2	1.349 (2)	C8—C9	1.535 (3)
C1—C2	1.506 (3)	C8—H8	0.9800
C2—C13	1.485 (2)	C9—H9A	0.9700
C2—C3	1.527 (2)	C9—H9B	0.9700
C2—H2	0.9800	C10—O3	1.206 (2)
C3—C5	1.520 (2)	C10—C11	1.507 (3)
C3—C4	1.530 (2)	C11—C12	1.530 (3)
C3—H3	0.9800	C11—H11A	0.9700
C4—O2	1.473 (2)	C11—H11B	0.9700
C4—C9	1.503 (2)	C12—H12A	0.9700
C4—H4	0.9800	C12—H12B	0.9700
C5—C6	1.545 (3)	C13—H13A	0.9600
C5—H5A	0.9700	C13—H13B	0.9600
C5—H5B	0.9700	C13—H13C	0.9600
C6—C10	1.525 (3)	C14—H14A	0.9600
C6—C14	1.546 (3)	C14—H14B	0.9600
C6—C7	1.558 (3)	C14—H14C	0.9600
C7—C8	1.544 (3)	C15—H15A	0.9600
C7—C12	1.545 (3)	C15—H15B	0.9600
C7—H7	0.9800	C15—H15C	0.9600
O1—C1—O2	121.39 (17)	C9—C8—H8	107.9
O1—C1—C2	128.53 (18)	C7—C8—H8	107.9
O2—C1—C2	110.08 (15)	C4—C9—C8	116.18 (15)
C13—C2—C1	114.00 (15)	C4—C9—H9A	108.2
C13—C2—C3	118.92 (16)	C8—C9—H9A	108.2
C1—C2—C3	103.43 (14)	C4—C9—H9B	108.2
C13—C2—H2	106.6	C8—C9—H9B	108.2
C1—C2—H2	106.6	H9A—C9—H9B	107.4
C3—C2—H2	106.6	O3—C10—C11	124.8 (2)
C5—C3—C2	113.67 (14)	O3—C10—C6	124.83 (19)
C5—C3—C4	115.01 (14)	C11—C10—C6	110.31 (17)
C2—C3—C4	102.93 (13)	C10—C11—C12	104.58 (18)
C5—C3—H3	108.3	C10—C11—H11A	110.8
C2—C3—H3	108.3	C12—C11—H11A	110.8
C4—C3—H3	108.3	C10—C11—H11B	110.8
O2—C4—C9	107.71 (13)	C12—C11—H11B	110.8
O2—C4—C3	104.38 (13)	H11A—C11—H11B	108.9
C9—C4—C3	115.32 (15)	C11—C12—C7	104.55 (16)
O2—C4—H4	109.7	C11—C12—H12A	110.8
C9—C4—H4	109.7	C7—C12—H12A	110.8
C3—C4—H4	109.7	C11—C12—H12B	110.8
C3—C5—C6	115.87 (13)	C7—C12—H12B	110.8
C3—C5—H5A	108.3	H12A—C12—H12B	108.9
C6—C5—H5A	108.3	C2—C13—H13A	109.5
C3—C5—H5B	108.3	C2—C13—H13B	109.5
C6—C5—H5B	108.3	H13A—C13—H13B	109.5
H5A—C5—H5B	107.4	C2—C13—H13C	109.5
C10—C6—C5	109.98 (14)	H13A—C13—H13C	109.5
C10—C6—C14	104.76 (16)	H13B—C13—H13C	109.5
C5—C6—C14	109.96 (15)	C6—C14—H14A	109.5
C10—C6—C7	103.01 (15)	C6—C14—H14B	109.5
C5—C6—C7	115.63 (14)	H14A—C14—H14B	109.5
C14—C6—C7	112.70 (14)	C6—C14—H14C	109.5
C8—C7—C12	113.76 (15)	H14A—C14—H14C	109.5
C8—C7—C6	116.85 (15)	H14B—C14—H14C	109.5
C12—C7—C6	103.16 (15)	C8—C15—H15A	109.5
C8—C7—H7	107.5	C8—C15—H15B	109.5
C12—C7—H7	107.5	H15A—C15—H15B	109.5
C6—C7—H7	107.5	C8—C15—H15C	109.5
C15—C8—C9	107.59 (17)	H15A—C15—H15C	109.5
C15—C8—C7	111.13 (17)	H15B—C15—H15C	109.5
C9—C8—C7	114.24 (14)	C1—O2—C4	110.89 (13)
C15—C8—H8	107.9