1-(4a,8-Dimethyl-1,2,3,4,4a,5,6,8a-octa-hydro-naphthalen-2-yl)-3-(4-methyl-phen-yl)prop-2-en-1-one.

The title compound, C(22)H(28)O, was isolated from the aerial part of Inula viscosa- (L) Aiton [or Dittrichia viscosa- (L) Greuter]. The cyclo-hexene ring has a half-chair conformation, whereas the cyclo-hexane ring displays a chair conformation being substituted at position 2 by a 3-(4-methyl-phen-yl)prop-2-enoyl group. In the crystal, weak inter-molecular C-H⋯O hydrogen bonds link mol-ecules into chains in the [010] direction.

Related literature

For background to the medicinal inter­est in Inula viscosa­ (L) Aiton [or Dittrichia viscosa­ (L) Greuter], see: Shtacher & Kasshman (1970 ▶); Bohlmann & Gupta (1982 ▶); Azoulay et al. (1986 ▶); Bohlmann et al. (1977 ▶); Ceccherelli et al. (1988 ▶). For details of the synthesis, see: Kutney & Singh (1984 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C22H28O

M = 308.44

Monoclinic,

a = 7.1577 (2) Å

b = 10.3456 (2) Å

c = 12.3663 (3) Å

β = 95.557 (1)°

V = 911.43 (4) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.37 × 0.16 × 0.16 mm

Data collection

Bruker X8 APEXII CCD area-detector diffractometer

8379 measured reflections

1957 independent reflections

1834 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.102

S = 1.11

1957 reflections

212 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.15 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 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811016941/cv5077sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016941/cv5077Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016941/cv5077Isup3.cml

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

C22H28O	F(000) = 336
Mr = 308.44	Dx = 1.124 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P2yb	Cell parameters from 8379 reflections
a = 7.1577 (2) Å	θ = 3.2–26.4°
b = 10.3456 (2) Å	µ = 0.07 mm−1
c = 12.3663 (3) Å	T = 298 K
β = 95.557 (1)°	Box, colourless
V = 911.43 (4) Å3	0.37 × 0.16 × 0.16 mm
Z = 2

Bruker X8 APEXII CCD area-detector diffractometer	1834 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.020
graphite	θmax = 26.4°, θmin = 3.2°
φ and ω scans	h = −8→8
8379 measured reflections	k = −12→10
1957 independent reflections	l = −15→15

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0586P)2 + 0.0808P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
1957 reflections	Δρmax = 0.16 e Å−3
212 parameters	Δρmin = −0.15 e Å−3
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.114 (14)

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
C8A	0.4720 (3)	0.6078 (2)	0.69374 (15)	0.0458 (4)
H1	0.4204	0.6593	0.7503	0.055*
C4A	0.5857 (3)	0.70276 (19)	0.62901 (16)	0.0479 (5)
C9	0.8915 (3)	0.4685 (2)	0.88054 (17)	0.0492 (5)
C1	0.5998 (3)	0.5063 (2)	0.75326 (15)	0.0452 (4)
H1B	0.5250	0.4505	0.7951	0.054*
H1A	0.6555	0.4531	0.7003	0.054*
C2	0.7557 (3)	0.5682 (2)	0.82916 (16)	0.0471 (4)
H2	0.6963	0.6105	0.8880	0.057*
C12	1.3719 (3)	0.4780 (2)	1.04958 (14)	0.0447 (4)
C8	0.3045 (3)	0.5531 (2)	0.62379 (16)	0.0496 (5)
C10	1.0489 (3)	0.5164 (2)	0.95720 (16)	0.0518 (5)
H10	1.0404	0.5971	0.9894	0.062*
C11	1.2020 (3)	0.4446 (2)	0.98015 (15)	0.0493 (5)
H11	1.2007	0.3633	0.9480	0.059*
C4	0.7317 (4)	0.7683 (2)	0.70850 (19)	0.0598 (6)
H4A	0.6678	0.8192	0.7595	0.072*
H4B	0.8056	0.8269	0.6687	0.072*
C15	1.7055 (3)	0.5343 (2)	1.18078 (17)	0.0551 (5)
C19	0.6825 (3)	0.6347 (2)	0.53984 (17)	0.0555 (5)
H19C	0.7554	0.6962	0.5038	0.083*
H19A	0.5894	0.5971	0.4881	0.083*
H19B	0.7634	0.5679	0.5716	0.083*
C14	1.6908 (3)	0.4253 (3)	1.11618 (17)	0.0579 (6)
H14	1.7930	0.3699	1.1158	0.069*
C13	1.5268 (3)	0.3968 (2)	1.05189 (16)	0.0536 (5)
H13	1.5202	0.3222	1.0097	0.064*
C17	1.3856 (3)	0.5877 (2)	1.11495 (17)	0.0523 (5)
H17	1.2836	0.6433	1.1155	0.063*
C18	0.2247 (3)	0.4273 (3)	0.65615 (18)	0.0600 (6)
H18A	0.1128	0.4086	0.6096	0.090*
H18C	0.1951	0.4323	0.7301	0.090*
H18B	0.3151	0.3598	0.6496	0.090*
C16	1.5503 (3)	0.6143 (2)	1.17911 (18)	0.0595 (6)
H16	1.5569	0.6881	1.2223	0.071*
C7	0.2281 (3)	0.6174 (3)	0.5375 (2)	0.0688 (7)
H7	0.1239	0.5806	0.4984	0.083*
C5	0.4492 (4)	0.8042 (2)	0.5771 (2)	0.0683 (7)
H5B	0.3912	0.8495	0.6338	0.082*
H5A	0.5187	0.8670	0.5386	0.082*
C3	0.8631 (3)	0.6731 (2)	0.77156 (19)	0.0602 (6)
H3B	0.9445	0.7200	0.8253	0.072*
H3A	0.9417	0.6319	0.7220	0.072*
C6	0.2963 (4)	0.7440 (3)	0.4981 (3)	0.0849 (9)
H6A	0.1913	0.8034	0.4874	0.102*
H6B	0.3451	0.7313	0.4284	0.102*
C20	1.8842 (4)	0.5651 (4)	1.2517 (2)	0.0800 (8)
H20A	1.9096	0.6560	1.2482	0.120*
H20C	1.9867	0.5176	1.2265	0.120*
H20B	1.8697	0.5412	1.3254	0.120*
O1	0.8777 (2)	0.35492 (17)	0.85675 (15)	0.0659 (5)

	U11	U22	U33	U12	U13	U23
C8A	0.0479 (10)	0.0461 (10)	0.0443 (9)	0.0035 (8)	0.0090 (7)	−0.0006 (8)
C4A	0.0543 (11)	0.0386 (10)	0.0515 (10)	0.0026 (8)	0.0083 (8)	0.0041 (8)
C9	0.0482 (10)	0.0496 (12)	0.0498 (10)	−0.0066 (9)	0.0054 (8)	0.0017 (9)
C1	0.0476 (10)	0.0413 (10)	0.0461 (9)	−0.0071 (8)	0.0016 (7)	0.0033 (8)
C2	0.0484 (10)	0.0463 (11)	0.0461 (9)	−0.0050 (9)	0.0020 (8)	−0.0024 (8)
C12	0.0469 (9)	0.0465 (10)	0.0408 (8)	−0.0001 (8)	0.0049 (7)	0.0069 (8)
C8	0.0400 (9)	0.0596 (12)	0.0498 (10)	0.0045 (9)	0.0070 (8)	0.0004 (9)
C10	0.0505 (10)	0.0529 (12)	0.0511 (10)	−0.0025 (9)	0.0006 (8)	−0.0003 (9)
C11	0.0531 (11)	0.0491 (12)	0.0459 (9)	−0.0033 (9)	0.0053 (8)	0.0019 (9)
C4	0.0737 (14)	0.0397 (11)	0.0655 (12)	−0.0098 (10)	0.0052 (11)	−0.0006 (10)
C15	0.0493 (11)	0.0641 (14)	0.0510 (10)	0.0016 (10)	0.0004 (8)	0.0092 (10)
C19	0.0603 (12)	0.0529 (13)	0.0552 (11)	−0.0008 (10)	0.0150 (9)	0.0040 (10)
C14	0.0507 (11)	0.0678 (15)	0.0560 (11)	0.0154 (11)	0.0089 (9)	0.0068 (11)
C13	0.0592 (12)	0.0517 (12)	0.0509 (10)	0.0087 (10)	0.0102 (8)	−0.0020 (9)
C17	0.0513 (11)	0.0448 (11)	0.0595 (11)	0.0079 (9)	−0.0010 (8)	0.0000 (9)
C18	0.0480 (11)	0.0705 (15)	0.0607 (12)	−0.0073 (10)	0.0009 (9)	−0.0006 (11)
C16	0.0622 (13)	0.0526 (12)	0.0614 (12)	0.0019 (11)	−0.0054 (10)	−0.0058 (10)
C7	0.0499 (12)	0.0862 (18)	0.0685 (14)	0.0054 (12)	−0.0034 (10)	0.0105 (13)
C5	0.0746 (15)	0.0512 (13)	0.0798 (15)	0.0151 (12)	0.0116 (12)	0.0171 (12)
C3	0.0608 (12)	0.0517 (12)	0.0655 (12)	−0.0199 (10)	−0.0073 (10)	0.0052 (11)
C6	0.0705 (16)	0.090 (2)	0.0911 (19)	0.0136 (16)	−0.0063 (14)	0.0377 (17)
C20	0.0566 (13)	0.098 (2)	0.0809 (16)	0.0032 (14)	−0.0141 (12)	0.0002 (16)
O1	0.0613 (9)	0.0470 (9)	0.0866 (11)	−0.0043 (7)	−0.0080 (8)	0.0008 (8)

C8A—C8	1.518 (3)	C15—C16	1.385 (3)
C8A—C1	1.534 (3)	C15—C20	1.513 (3)
C8A—C4A	1.547 (3)	C19—H19C	0.9600
C8A—H1	0.9800	C19—H19A	0.9600
C4A—C4	1.523 (3)	C19—H19B	0.9600
C4A—C19	1.530 (3)	C14—C13	1.384 (3)
C4A—C5	1.532 (3)	C14—H14	0.9300
C9—O1	1.213 (3)	C13—H13	0.9300
C9—C10	1.485 (3)	C17—C16	1.383 (3)
C9—C2	1.514 (3)	C17—H17	0.9300
C1—C2	1.528 (3)	C18—H18A	0.9600
C1—H1B	0.9700	C18—H18C	0.9600
C1—H1A	0.9700	C18—H18B	0.9600
C2—C3	1.543 (3)	C16—H16	0.9300
C2—H2	0.9800	C7—C6	1.496 (5)
C12—C13	1.389 (3)	C7—H7	0.9300
C12—C17	1.391 (3)	C5—C6	1.528 (4)
C12—C11	1.460 (3)	C5—H5B	0.9700
C8—C7	1.329 (3)	C5—H5A	0.9700
C8—C18	1.492 (3)	C3—H3B	0.9700
C10—C11	1.332 (3)	C3—H3A	0.9700
C10—H10	0.9300	C6—H6A	0.9700
C11—H11	0.9300	C6—H6B	0.9700
C4—C3	1.523 (3)	C20—H20A	0.9600
C4—H4A	0.9700	C20—H20C	0.9600
C4—H4B	0.9700	C20—H20B	0.9600
C15—C14	1.380 (4)
C8—C8A—C1	114.82 (17)	H19C—C19—H19A	109.5
C8—C8A—C4A	111.57 (16)	C4A—C19—H19B	109.5
C1—C8A—C4A	111.33 (16)	H19C—C19—H19B	109.5
C8—C8A—H1	106.1	H19A—C19—H19B	109.5
C1—C8A—H1	106.1	C15—C14—C13	121.3 (2)
C4A—C8A—H1	106.1	C15—C14—H14	119.3
C4—C4A—C19	109.86 (18)	C13—C14—H14	119.3
C4—C4A—C5	109.59 (19)	C14—C13—C12	120.9 (2)
C19—C4A—C5	109.17 (17)	C14—C13—H13	119.6
C4—C4A—C8A	108.12 (16)	C12—C13—H13	119.6
C19—C4A—C8A	112.23 (17)	C16—C17—C12	120.3 (2)
C5—C4A—C8A	107.82 (17)	C16—C17—H17	119.9
O1—C9—C10	121.1 (2)	C12—C17—H17	119.9
O1—C9—C2	121.63 (19)	C8—C18—H18A	109.5
C10—C9—C2	117.21 (19)	C8—C18—H18C	109.5
C2—C1—C8A	111.96 (16)	H18A—C18—H18C	109.5
C2—C1—H1B	109.2	C8—C18—H18B	109.5
C8A—C1—H1B	109.2	H18A—C18—H18B	109.5
C2—C1—H1A	109.2	H18C—C18—H18B	109.5
C8A—C1—H1A	109.2	C17—C16—C15	121.8 (2)
H1B—C1—H1A	107.9	C17—C16—H16	119.1
C9—C2—C1	111.90 (17)	C15—C16—H16	119.1
C9—C2—C3	110.14 (17)	C8—C7—C6	125.3 (3)
C1—C2—C3	112.23 (15)	C8—C7—H7	117.4
C9—C2—H2	107.4	C6—C7—H7	117.4
C1—C2—H2	107.4	C6—C5—C4A	112.1 (2)
C3—C2—H2	107.4	C6—C5—H5B	109.2
C13—C12—C17	118.05 (19)	C4A—C5—H5B	109.2
C13—C12—C11	119.1 (2)	C6—C5—H5A	109.2
C17—C12—C11	122.84 (19)	C4A—C5—H5A	109.2
C7—C8—C18	120.9 (2)	H5B—C5—H5A	107.9
C7—C8—C8A	120.8 (2)	C4—C3—C2	112.33 (19)
C18—C8—C8A	118.30 (18)	C4—C3—H3B	109.1
C11—C10—C9	120.5 (2)	C2—C3—H3B	109.1
C11—C10—H10	119.7	C4—C3—H3A	109.1
C9—C10—H10	119.7	C2—C3—H3A	109.1
C10—C11—C12	127.9 (2)	H3B—C3—H3A	107.9
C10—C11—H11	116.0	C7—C6—C5	112.6 (2)
C12—C11—H11	116.0	C7—C6—H6A	109.1
C4A—C4—C3	113.21 (18)	C5—C6—H6A	109.1
C4A—C4—H4A	108.9	C7—C6—H6B	109.1
C3—C4—H4A	108.9	C5—C6—H6B	109.1
C4A—C4—H4B	108.9	H6A—C6—H6B	107.8
C3—C4—H4B	108.9	C15—C20—H20A	109.5
H4A—C4—H4B	107.7	C15—C20—H20C	109.5
C14—C15—C16	117.64 (19)	H20A—C20—H20C	109.5
C14—C15—C20	121.4 (2)	C15—C20—H20B	109.5
C16—C15—C20	121.0 (2)	H20A—C20—H20B	109.5
C4A—C19—H19C	109.5	H20C—C20—H20B	109.5
C4A—C19—H19A	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C17—H17···O1i	0.93	2.51	3.383 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17⋯O1i	0.93	2.51	3.383 (3)	156

Symmetry code: (i) .