6,6,9a-Trimethyl-5,5a,6,7,8,9,9a,9b-octa-hydro-naphtho[1,2-c]furan-1(3H)-one.

In the crystal structure of the title compound, C(15)H(22)O(2), the cyclo-hexene and cyclo-hexane rings adopt half-boat and chair conformations, respectively, and the lactone ring is in an envelope conformation.

Related literature

For related literature, see: Almeida et al. (2001 ▶); Appel et al. (1963 ▶); Cremer & Pople (1975 ▶); Cruz et al. (1973 ▶); Harinantenaina et al. (2007 ▶); Sierra et al. (1986 ▶).

Experimental

Crystal data

C15H22O2

M = 234.33

Orthorhombic,

a = 7.4031 (2) Å

b = 7.9250 (2) Å

c = 22.9973 (8) Å

V = 1349.24 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 298 (2) K

0.14 × 0.12 × 0.08 mm

Data collection

Nonius KappaCCD area-detector diffractometer

Absorption correction: none

4453 measured reflections

1790 independent reflections

1645 reflections with I > 2σ(I)

R int = 0.066

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.167

S = 1.18

1790 reflections

163 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.19 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO–SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO–SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2003 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808007460/nc2094sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808007460/nc2094Isup2.hkl

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

C15H22O2	F000 = 512
Mr = 234.33	Dx = 1.154 Mg m−3
Orthorhombic, P212121	Mo Kα radiation λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4453 reflections
a = 7.4031 (2) Å	θ = 2.7–27.5º
b = 7.9250 (2) Å	µ = 0.07 mm−1
c = 22.9973 (8) Å	T = 298 (2) K
V = 1349.24 (7) Å3	Prism, colourless
Z = 4	0.14 × 0.12 × 0.08 mm

Nonius KappaCCD area-detector diffractometer	1645 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.066
Monochromator: graphite	θmax = 27.5º
φ scans, and ω scans with κ offsets	θmin = 2.7º
Absorption correction: none	h = −9→9
4453 measured reflections	k = −10→10
1790 independent reflections	l = −29→29

Refinement on F2	H atoms treated by a mixture of independent and constrained refinement
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0906P)2 + 0.1776P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.061	(Δ/σ)max = 0.001
wR(F2) = 0.167	Δρmax = 0.23 e Å−3
S = 1.18	Δρmin = −0.19 e Å−3
1790 reflections	Extinction correction: none
163 parameters

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	0.8222 (4)	0.4735 (2)	0.79867 (11)	0.0726 (8)
O2	0.6477 (3)	0.2766 (3)	0.76017 (10)	0.0656 (7)
C1	0.7967 (4)	0.3267 (3)	0.78912 (12)	0.0513 (7)
C3	0.6436 (5)	0.0949 (4)	0.75322 (14)	0.0609 (8)
H3A	0.6714	0.0632	0.7135	0.077 (3)*
H3B	0.5261	0.0499	0.7635	0.077 (3)*
C3A	0.7862 (4)	0.0326 (3)	0.79414 (10)	0.0427 (6)
C4	0.7941 (4)	−0.1115 (3)	0.82241 (13)	0.0537 (7)
H4	0.712 (4)	−0.196 (4)	0.8180 (12)	0.052 (8)*
C5	0.9382 (5)	−0.1455 (4)	0.86662 (14)	0.0607 (8)
H5A	0.9938	−0.2535	0.858	0.077 (3)*
H5B	0.8825	−0.1539	0.9047	0.077 (3)*
C5A	1.0857 (4)	−0.0101 (3)	0.86874 (10)	0.0400 (5)
H5A1	1.1546	−0.0261	0.8328	0.077 (3)*
C6	1.2257 (4)	−0.0397 (4)	0.91848 (12)	0.0533 (7)
C7	1.3670 (4)	0.1013 (5)	0.91648 (15)	0.0648 (8)
H7A	1.4451	0.0906	0.9501	0.077 (3)*
H7B	1.4411	0.086	0.8821	0.077 (3)*
C8	1.2894 (5)	0.2776 (5)	0.91553 (17)	0.0701 (9)
H8A	1.3868	0.3592	0.9131	0.077 (3)*
H8B	1.2234	0.2982	0.9513	0.077 (3)*
C9	1.1637 (4)	0.2991 (4)	0.86386 (14)	0.0573 (7)
H9A	1.2326	0.2857	0.8283	0.077 (3)*
H9B	1.1148	0.4126	0.8642	0.077 (3)*
C9A	1.0067 (3)	0.1719 (3)	0.86379 (10)	0.0383 (5)
C9B	0.9142 (3)	0.1759 (3)	0.80383 (10)	0.0391 (5)
H9B1	1.009	0.1684	0.7742	0.077 (3)*
C10	0.8694 (4)	0.2156 (4)	0.91074 (12)	0.0587 (8)
H10A	0.9297	0.2262	0.9475	0.100 (5)*
H10B	0.7804	0.1278	0.9131	0.100 (5)*
H10C	0.8114	0.3204	0.9012	0.100 (5)*
C11	1.1446 (6)	−0.0480 (6)	0.97981 (13)	0.0809 (11)
H11A	1.0476	−0.1284	0.9804	0.100 (5)*
H11B	1.0992	0.0612	0.9905	0.100 (5)*
H11C	1.2361	−0.0819	1.007	0.100 (5)*
C12	1.3245 (6)	−0.2074 (5)	0.90694 (18)	0.0871 (12)
H12A	1.4199	−0.2213	0.9348	0.100 (5)*
H12B	1.3744	−0.2062	0.8684	0.100 (5)*
H12C	1.2406	−0.2993	0.9104	0.100 (5)*

	U11	U22	U33	U12	U13	U23
O1	0.0919 (18)	0.0321 (10)	0.0938 (17)	0.0012 (11)	−0.0179 (15)	−0.0003 (9)
O2	0.0735 (13)	0.0419 (11)	0.0814 (14)	0.0128 (10)	−0.0286 (13)	−0.0048 (9)
C1	0.0645 (17)	0.0336 (13)	0.0558 (15)	0.0033 (13)	−0.0039 (14)	−0.0002 (10)
C3	0.0734 (19)	0.0432 (15)	0.0660 (18)	0.0044 (14)	−0.0219 (17)	−0.0077 (12)
C3A	0.0499 (14)	0.0330 (12)	0.0450 (13)	0.0001 (11)	−0.0071 (12)	−0.0062 (9)
C4	0.0597 (17)	0.0348 (12)	0.0667 (17)	−0.0153 (12)	−0.0151 (15)	−0.0006 (12)
C5	0.0749 (19)	0.0385 (14)	0.0686 (18)	−0.0126 (14)	−0.0193 (17)	0.0144 (12)
C5A	0.0446 (12)	0.0372 (12)	0.0384 (11)	−0.0012 (11)	−0.0037 (10)	0.0012 (9)
C6	0.0537 (15)	0.0590 (16)	0.0473 (14)	0.0056 (14)	−0.0096 (13)	0.0042 (12)
C7	0.0441 (15)	0.091 (2)	0.0595 (17)	−0.0051 (16)	−0.0102 (15)	−0.0033 (16)
C8	0.0543 (16)	0.072 (2)	0.084 (2)	−0.0206 (16)	−0.0167 (17)	−0.0073 (17)
C9	0.0545 (16)	0.0464 (15)	0.0709 (17)	−0.0171 (14)	−0.0049 (15)	0.0000 (13)
C9A	0.0395 (11)	0.0348 (11)	0.0405 (11)	−0.0083 (10)	0.0023 (10)	−0.0025 (9)
C9B	0.0453 (12)	0.0311 (11)	0.0410 (11)	−0.0017 (11)	0.0025 (10)	−0.0006 (9)
C10	0.0536 (15)	0.075 (2)	0.0476 (15)	0.0070 (15)	0.0044 (13)	−0.0152 (14)
C11	0.084 (2)	0.112 (3)	0.0464 (16)	−0.013 (3)	−0.0105 (17)	0.0190 (17)
C12	0.094 (3)	0.079 (2)	0.088 (3)	0.029 (2)	−0.040 (2)	−0.0022 (19)

O1—C1	1.199 (3)	C7—H7A	0.97
O2—C1	1.348 (4)	C7—H7B	0.97
O2—C3	1.449 (4)	C8—C9	1.519 (5)
C1—C9B	1.516 (3)	C8—H8A	0.97
C3—C3A	1.498 (4)	C8—H8B	0.97
C3—H3A	0.97	C9—C9A	1.538 (3)
C3—H3B	0.97	C9—H9A	0.97
C3A—C4	1.315 (4)	C9—H9B	0.97
C3A—C9B	1.496 (3)	C9A—C10	1.523 (4)
C4—C5	1.498 (4)	C9A—C9B	1.540 (3)
C4—H4	0.91 (3)	C9B—H9B1	0.98
C5—C5A	1.532 (4)	C10—H10A	0.96
C5—H5A	0.97	C10—H10B	0.96
C5—H5B	0.97	C10—H10C	0.96
C5A—C9A	1.560 (3)	C11—H11A	0.96
C5A—C6	1.561 (3)	C11—H11B	0.96
C5A—H5A1	0.98	C11—H11C	0.96
C6—C7	1.531 (4)	C12—H12A	0.96
C6—C11	1.534 (4)	C12—H12B	0.96
C6—C12	1.540 (5)	C12—H12C	0.96
C7—C8	1.511 (5)
C1—O2—C3	111.4 (2)	C7—C8—H8A	109.6
O1—C1—O2	120.4 (3)	C9—C8—H8A	109.6
O1—C1—C9B	129.3 (3)	C7—C8—H8B	109.6
O2—C1—C9B	110.3 (2)	C9—C8—H8B	109.6
O2—C3—C3A	104.1 (2)	H8A—C8—H8B	108.1
O2—C3—H3A	110.9	C8—C9—C9A	113.0 (2)
C3A—C3—H3A	110.9	C8—C9—H9A	109
O2—C3—H3B	110.9	C9A—C9—H9A	109
C3A—C3—H3B	110.9	C8—C9—H9B	109
H3A—C3—H3B	108.9	C9A—C9—H9B	109
C4—C3A—C9B	123.9 (2)	H9A—C9—H9B	107.8
C4—C3A—C3	128.9 (3)	C10—C9A—C9	110.8 (2)
C9B—C3A—C3	106.8 (2)	C10—C9A—C9B	109.5 (2)
C3A—C4—C5	121.6 (2)	C9—C9A—C9B	108.9 (2)
C3A—C4—H4	123.5 (19)	C10—C9A—C5A	114.1 (2)
C5—C4—H4	114.9 (19)	C9—C9A—C5A	108.8 (2)
C4—C5—C5A	113.8 (2)	C9B—C9A—C5A	104.53 (18)
C4—C5—H5A	108.8	C3A—C9B—C1	101.6 (2)
C5A—C5—H5A	108.8	C3A—C9B—C9A	113.53 (19)
C4—C5—H5B	108.8	C1—C9B—C9A	118.1 (2)
C5A—C5—H5B	108.8	C3A—C9B—H9B1	107.7
H5A—C5—H5B	107.7	C1—C9B—H9B1	107.7
C5—C5A—C9A	112.2 (2)	C9A—C9B—H9B1	107.7
C5—C5A—C6	113.0 (2)	C9A—C10—H10A	109.5
C9A—C5A—C6	116.2 (2)	C9A—C10—H10B	109.5
C5—C5A—H5A1	104.7	H10A—C10—H10B	109.5
C9A—C5A—H5A1	104.7	C9A—C10—H10C	109.5
C6—C5A—H5A1	104.7	H10A—C10—H10C	109.5
C7—C6—C11	109.1 (3)	H10B—C10—H10C	109.5
C7—C6—C12	107.5 (3)	C6—C11—H11A	109.5
C11—C6—C12	107.9 (3)	C6—C11—H11B	109.5
C7—C6—C5A	108.8 (2)	H11A—C11—H11B	109.5
C11—C6—C5A	114.8 (3)	C6—C11—H11C	109.5
C12—C6—C5A	108.6 (2)	H11A—C11—H11C	109.5
C8—C7—C6	114.5 (2)	H11B—C11—H11C	109.5
C8—C7—H7A	108.6	C6—C12—H12A	109.5
C6—C7—H7A	108.6	C6—C12—H12B	109.5
C8—C7—H7B	108.6	H12A—C12—H12B	109.5
C6—C7—H7B	108.6	C6—C12—H12C	109.5
H7A—C7—H7B	107.6	H12A—C12—H12C	109.5
C7—C8—C9	110.4 (3)	H12B—C12—H12C	109.5
C3—O2—C1—O1	179.8 (3)	C8—C9—C9A—C9B	−167.1 (3)
C3—O2—C1—C9B	1.3 (3)	C8—C9—C9A—C5A	−53.7 (3)
C1—O2—C3—C3A	13.5 (4)	C5—C5A—C9A—C10	57.9 (3)
O2—C3—C3A—C4	150.1 (3)	C6—C5A—C9A—C10	−74.3 (3)
O2—C3—C3A—C9B	−23.0 (3)	C5—C5A—C9A—C9	−177.8 (2)
C9B—C3A—C4—C5	−1.5 (5)	C6—C5A—C9A—C9	50.0 (3)
C3—C3A—C4—C5	−173.5 (3)	C5—C5A—C9A—C9B	−61.6 (3)
C3A—C4—C5—C5A	−8.2 (4)	C6—C5A—C9A—C9B	166.2 (2)
C4—C5—C5A—C9A	41.4 (3)	C4—C3A—C9B—C1	−150.4 (3)
C4—C5—C5A—C6	175.2 (3)	C3—C3A—C9B—C1	23.0 (3)
C5—C5A—C6—C7	179.6 (3)	C4—C3A—C9B—C9A	−22.6 (4)
C9A—C5A—C6—C7	−48.5 (3)	C3—C3A—C9B—C9A	150.9 (2)
C5—C5A—C6—C11	−57.9 (4)	O1—C1—C9B—C3A	166.3 (3)
C9A—C5A—C6—C11	74.0 (3)	O2—C1—C9B—C3A	−15.4 (3)
C5—C5A—C6—C12	63.0 (3)	O1—C1—C9B—C9A	41.4 (4)
C9A—C5A—C6—C12	−165.2 (3)	O2—C1—C9B—C9A	−140.3 (2)
C11—C6—C7—C8	−74.4 (3)	C10—C9A—C9B—C3A	−71.3 (3)
C12—C6—C7—C8	168.9 (3)	C9—C9A—C9B—C3A	167.5 (2)
C5A—C6—C7—C8	51.5 (3)	C5A—C9A—C9B—C3A	51.4 (3)
C6—C7—C8—C9	−57.5 (4)	C10—C9A—C9B—C1	47.6 (3)
C7—C8—C9—C9A	58.3 (4)	C9—C9A—C9B—C1	−73.7 (3)
C8—C9—C9A—C10	72.5 (3)	C5A—C9A—C9B—C1	170.2 (2)