Fraxinellone.

In the title compound, C(14)H(16)O(3) [systematic name: (3R*,3aR*)-3-(3-furan-yl)-3a,7-dimethyl-3a,4,5,6-tetra-hydro-2-benzofuran-1(3H)-one], the pendant methyl and furan groups attached to the stereogenic centres lie to the same side of the fused ring system. The dihedral angle between the five-membered rings is 74.8 (2)°; the fused five-membered ring adopts a twisted conformation. In the crystal, mol-ecules are linked by weak C-H⋯O inter-actions, which generate [100] chains.

Related literature

For background to fraxinellone and its biological activity, see: Kim et al. (2009 ▶); Sun et al. (2009 ▶); Liu et al. (2009 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H16O3

M = 232.27

Orthorhombic,

a = 5.940 (3) Å

b = 12.661 (6) Å

c = 15.921 (7) Å

V = 1197.3 (9) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.20 × 0.18 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.982, T max = 0.984

10397 measured reflections

1733 independent reflections

1331 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.113

S = 1.07

1733 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.17 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXL97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018393/hb5863sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811018393/hb5863Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811018393/hb5863Isup3.cml

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

C14H16O3	F(000) = 496
Mr = 232.27	Dx = 1.288 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 5.940 (3) Å	θ = 9–12°
b = 12.661 (6) Å	µ = 0.09 mm−1
c = 15.921 (7) Å	T = 298 K
V = 1197.3 (9) Å3	Block, colorless
Z = 4	0.20 × 0.20 × 0.18 mm

Bruker SMART CCD diffractometer	1733 independent reflections
Radiation source: fine-focus sealed tube	1331 reflections with I > 2σ(I)
graphite	Rint = 0.049
φ and ω scans	θmax = 28.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −7→7
Tmin = 0.982, Tmax = 0.984	k = −17→16
10397 measured reflections	l = −19→21

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.113	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0425P)2 + 0.1558P] where P = (Fo2 + 2Fc2)/3
1733 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.12 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	0.5425 (3)	−0.10394 (15)	0.61505 (12)	0.0558 (5)
O2	0.2594 (3)	0.00000 (13)	0.65310 (9)	0.0423 (4)
O3	−0.2584 (5)	0.24662 (18)	0.72681 (14)	0.0806 (8)
C1	0.3749 (4)	−0.05682 (18)	0.59460 (15)	0.0391 (5)
C2	0.2628 (4)	−0.04409 (17)	0.51292 (14)	0.0377 (5)
C3	0.2806 (5)	−0.10573 (18)	0.44505 (15)	0.0428 (6)
C4	0.1270 (5)	−0.0894 (2)	0.37091 (17)	0.0571 (7)
H4A	0.0334	−0.1517	0.3649	0.069*
H4B	0.2190	−0.0840	0.3208	0.069*
C5	−0.0254 (5)	0.0067 (2)	0.37495 (17)	0.0583 (7)
H5A	−0.1572	−0.0058	0.3404	0.070*
H5B	0.0539	0.0671	0.3520	0.070*
C6	−0.1009 (4)	0.0323 (2)	0.46465 (16)	0.0488 (6)
H6A	−0.1916	0.0960	0.4645	0.059*
H6B	−0.1925	−0.0251	0.4862	0.059*
C7	0.1041 (4)	0.04793 (17)	0.52105 (13)	0.0355 (5)
C8	0.0486 (4)	0.03908 (17)	0.61578 (14)	0.0364 (5)
H8	−0.0667	−0.0156	0.6228	0.044*
C9	0.4404 (5)	−0.1978 (2)	0.4381 (2)	0.0599 (8)
H9A	0.5589	−0.1806	0.3995	0.090*
H9B	0.3603	−0.2587	0.4181	0.090*
H9C	0.5037	−0.2127	0.4923	0.090*
C10	0.2300 (5)	0.15067 (19)	0.50129 (15)	0.0466 (6)
H10A	0.3577	0.1572	0.5379	0.070*
H10B	0.1311	0.2097	0.5096	0.070*
H10C	0.2802	0.1495	0.4440	0.070*
C11	−0.0265 (4)	0.13529 (19)	0.66193 (14)	0.0416 (6)
C12	−0.2403 (6)	0.1508 (2)	0.68932 (16)	0.0563 (7)
H12	−0.3574	0.1026	0.6833	0.068*
C13	−0.0487 (6)	0.2921 (2)	0.72441 (18)	0.0579 (8)
H13	−0.0116	0.3577	0.7467	0.069*
C14	0.0930 (6)	0.2275 (2)	0.68509 (17)	0.0542 (7)
H14	0.2445	0.2406	0.6746	0.065*

	U11	U22	U33	U12	U13	U23
O1	0.0482 (11)	0.0579 (10)	0.0612 (11)	0.0135 (10)	−0.0039 (10)	0.0022 (9)
O2	0.0457 (9)	0.0438 (8)	0.0372 (8)	0.0068 (8)	0.0002 (8)	0.0015 (7)
O3	0.101 (2)	0.0835 (16)	0.0576 (12)	0.0376 (17)	0.0124 (14)	−0.0099 (11)
C1	0.0405 (13)	0.0328 (11)	0.0441 (13)	−0.0013 (11)	0.0046 (11)	0.0044 (10)
C2	0.0383 (13)	0.0356 (11)	0.0391 (12)	−0.0052 (11)	0.0047 (11)	0.0025 (9)
C3	0.0415 (14)	0.0389 (12)	0.0480 (14)	−0.0062 (11)	0.0090 (12)	−0.0047 (10)
C4	0.0623 (18)	0.0652 (16)	0.0438 (15)	−0.0026 (16)	0.0025 (14)	−0.0105 (13)
C5	0.0666 (19)	0.0645 (16)	0.0438 (14)	0.0014 (16)	−0.0078 (14)	−0.0009 (13)
C6	0.0476 (15)	0.0539 (15)	0.0449 (14)	0.0050 (13)	−0.0071 (12)	−0.0008 (12)
C7	0.0375 (12)	0.0348 (11)	0.0342 (11)	0.0006 (10)	0.0034 (10)	0.0013 (9)
C8	0.0351 (12)	0.0373 (11)	0.0369 (11)	0.0000 (10)	0.0024 (10)	0.0023 (9)
C9	0.0583 (19)	0.0508 (15)	0.0708 (19)	0.0022 (15)	0.0055 (16)	−0.0183 (14)
C10	0.0561 (16)	0.0385 (11)	0.0451 (13)	−0.0066 (13)	0.0066 (14)	0.0048 (10)
C11	0.0467 (15)	0.0454 (13)	0.0326 (11)	0.0058 (12)	0.0009 (11)	0.0024 (10)
C12	0.0607 (18)	0.0642 (16)	0.0439 (14)	0.0099 (16)	0.0075 (16)	−0.0036 (13)
C13	0.082 (2)	0.0455 (14)	0.0465 (15)	0.0112 (16)	−0.0031 (16)	−0.0107 (12)
C14	0.0634 (19)	0.0508 (14)	0.0485 (15)	−0.0008 (15)	−0.0041 (15)	−0.0052 (12)

O1—C1	1.205 (3)	C6—H6B	0.9700
O2—C1	1.362 (3)	C7—C10	1.533 (3)
O2—C8	1.471 (3)	C7—C8	1.548 (3)
O3—C12	1.357 (3)	C8—C11	1.491 (3)
O3—C13	1.373 (4)	C8—H8	0.9800
C1—C2	1.470 (3)	C9—H9A	0.9600
C2—C3	1.337 (3)	C9—H9B	0.9600
C2—C7	1.504 (3)	C9—H9C	0.9600
C3—C4	1.506 (4)	C10—H10A	0.9600
C3—C9	1.507 (4)	C10—H10B	0.9600
C4—C5	1.518 (4)	C10—H10C	0.9600
C4—H4A	0.9700	C11—C12	1.357 (4)
C4—H4B	0.9700	C11—C14	1.415 (4)
C5—C6	1.531 (4)	C12—H12	0.9300
C5—H5A	0.9700	C13—C14	1.331 (4)
C5—H5B	0.9700	C13—H13	0.9300
C6—C7	1.526 (3)	C14—H14	0.9300
C6—H6A	0.9700
C1—O2—C8	109.29 (17)	C6—C7—C8	113.2 (2)
C12—O3—C13	106.9 (3)	C10—C7—C8	111.41 (18)
O1—C1—O2	119.5 (2)	O2—C8—C11	109.30 (19)
O1—C1—C2	131.9 (2)	O2—C8—C7	103.70 (17)
O2—C1—C2	108.6 (2)	C11—C8—C7	119.00 (18)
C3—C2—C1	128.0 (2)	O2—C8—H8	108.1
C3—C2—C7	124.8 (2)	C11—C8—H8	108.1
C1—C2—C7	107.02 (18)	C7—C8—H8	108.1
C2—C3—C4	120.4 (2)	C3—C9—H9A	109.5
C2—C3—C9	124.1 (3)	C3—C9—H9B	109.5
C4—C3—C9	115.5 (2)	H9A—C9—H9B	109.5
C3—C4—C5	116.0 (2)	C3—C9—H9C	109.5
C3—C4—H4A	108.3	H9A—C9—H9C	109.5
C5—C4—H4A	108.3	H9B—C9—H9C	109.5
C3—C4—H4B	108.3	C7—C10—H10A	109.5
C5—C4—H4B	108.3	C7—C10—H10B	109.5
H4A—C4—H4B	107.4	H10A—C10—H10B	109.5
C4—C5—C6	112.6 (2)	C7—C10—H10C	109.5
C4—C5—H5A	109.1	H10A—C10—H10C	109.5
C6—C5—H5A	109.1	H10B—C10—H10C	109.5
C4—C5—H5B	109.1	C12—C11—C14	105.5 (2)
C6—C5—H5B	109.1	C12—C11—C8	123.8 (3)
H5A—C5—H5B	107.8	C14—C11—C8	130.7 (2)
C7—C6—C5	110.0 (2)	C11—C12—O3	110.2 (3)
C7—C6—H6A	109.7	C11—C12—H12	124.9
C5—C6—H6A	109.7	O3—C12—H12	124.9
C7—C6—H6B	109.7	C14—C13—O3	109.2 (2)
C5—C6—H6B	109.7	C14—C13—H13	125.4
H6A—C6—H6B	108.2	O3—C13—H13	125.4
C2—C7—C6	110.41 (19)	C13—C14—C11	108.2 (3)
C2—C7—C10	109.49 (19)	C13—C14—H14	125.9
C6—C7—C10	112.3 (2)	C11—C14—H14	125.9
C2—C7—C8	99.28 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···O1i	0.98	2.58	3.510 (3)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯O1i	0.98	2.58	3.510 (3)	158

Symmetry code: (i) .