1-(4a,8-Dimethyl-1,2,3,4,4a,5,6,8a-octa­hydro­naphthalen-2-yl)-3-(4-methyl­phen­yl)prop-2-en-1-one

Tebbaa, M.; Benharref, A.; Berraho, M.; Avignant, D.; Oudahmane, A.; Akssira, M.

doi:10.1107/S1600536811016941

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Page o1381

doi:10.1107/S1600536811016941

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1-(4a,8-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl)-3-(4-methylphenyl)prop-2-en-1-one

Mohamed Tebbaa,^a ^* Ahmed Benharref,^b Moha Berraho,^b Daniel Avignant,^c Abdelghani Oudahmane ^c and Mohamed Akssira ^a

^aLaboratoire de Chimie Bioorganique et Analytique, URAC 22, BP 146, FSTM, Université Hassan II, Mohammedia-Casablanca 20810 Mohammedia, Morocco, ^bLaboratoire de Chimie Biomoleculaire, Substances Naturelles et Réactivité, URAC16, Université Cadi Ayyad, Faculté des Sciences Semlalia, BP 2390, Boulevard My Abdellah, 40000 Marrakech, Morocco, and ^cUniversité Blaise Pascal, Laboratoire des Matériaux Inorganiques, UMR CNRS 6002, 24 Avenue des Landais, 63177 Aubière, France
^*Correspondence e-mail: mtebbaa@yahoo.com

(Received 17 April 2011; accepted 5 May 2011; online 11 May 2011)

The title compound, C₂₂H₂₈O, was isolated from the aerial part of Inula viscosa (L) Aiton [or Dittrichia viscosa (L) Greuter]. The cyclohexene ring has a half-chair conformation, whereas the cyclohexane ring displays a chair conformation being substituted at position 2 by a 3-(4-methylphenyl)prop-2-enoyl group. In the crystal, weak intermolecular C—H⋯O hydrogen bonds link molecules 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_r = 308.44
Monoclinic, P 2₁
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.102
S = 1.11
1957 reflections
212 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.15 e Å⁻³

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) $[-x+2, y+{\script{1\over 2}}, -z+2]$ .

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 ).

Supporting information

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

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

Supporting information file. DOI: 10.1107/S1600536811016941/cv5077Isup3.cml

checkCIF report

Comment top

Our work lies within the framework of the valorization of medicinal plants and concerns Inula Viscosa (L) Aiton or Dittrichia Viscosa (L) Greuter. This plant is widespread in Mediterranean area and extends to the Atlantic cost of Morocco. It is a well known medicinal plant (Shtacher & Kasshman, 1970; Bohlmann & Gupta, 1982), which exhibits some pharmacological activities (Azoulay et al., 1986). This plant has been the subject of chemical investigation in terms of isolating sesquiterpene lactones (Bohlmann et al., 1977) and sesquiterpene acids (Ceccherelli et al., 1988). The isocostic acid is a major constituent of the dichloromethane extract of the Inula viscosa (L). The literature does not report any results on the transformation of this acid. In order to prepare products with high added value, we studied the reactivity of this acid. Thus, from this acid, we have prepared by reaction of Curtius the 1 - (4a, 8dimethyl-1,2,3,4, 4a,5,6,8a-octahydronaphthalen-2-yl)-ethanone, which was synthesized by Kutney et al. (1984). The condensation of this ketone with para- methylbenzaldehyde in the presence of sodium hydroxide allowed us to obtain the title compound (I) with a good yield of 80%. The structure of this new derivative of isocostic acid was established by NMR spectral analysis of 1H, 13 C and mass spectroscopy and confirmed by its single-crystal X-ray structure.

The molecule of (I) is built up from two fused six-membered rings, substituted at position 2 by 4-methylphenylpropenoyl group The molecular structure of (I), Fig.1, shows the cyclohexane ring to adopt a chair conformation, as indicated by the total puckering amplitude QT = 0.5617 (17)Å and spherical polar angle θ =7.25 (17)° with ϕ = 260.6 (14)°. While the cyclohexene ring has a half chair conformation with QT = 0.5071 (18) Å, θ =49.7 (2)°, ϕ = 12.5 (6)° (Cremer & Pople, 1975). In the crystal structure, weak intermolecular C—H···O hydrogen bonds (Table 1) link molecules into chains in [010] (Fig. 2).

Related literature top

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 top

In a flask was introduced a mixture of 500 mg (2.42 mmol), of 1 - (4a, 8-dimethyl-1, 2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl)-ethanone, 257 mg (2.42 mmol.) of para chlor-benzaldehyde, 30 ml of anhydrous ethanol and 1 ml of a solution of sodium hydroxide(2 N). The mixture was stirred for three hours at room temperature. After neutralization followed by extraction three time with 20 ml of dichloromethane, the organic phase is dried over sodium sulfate, then evaporated under vacuum. Chromatography on a column of silica gel with hexane-ethyl acetate (97/3) as eluent of the residue allowed us to obtain 3-(4-méthylphenyl)-1-(4a, 8-dimethyl-1,2,3,4,4a, 5,6,8a-octahydronaphthalen-2-yl)prop-2-en-1-one with a yield of 80%. The title compound is recrystallized in hexane-ethyl acetate (70/30).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

	Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. A portion of the crystal packing showing hydrogen-bonded (dashed lines) chains of the molecules. H atoms not involved in hydrogen bonding have been omitted for clarity.

1-(4a,8-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl)- 3-(4-methylphenyl)prop-2-en-1-one top

Crystal data top

C₂₂H₂₈O	F(000) = 336
M_r = 308.44	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0586P)² + 0.0808P] where P = (F_o² + 2F_c²)/3
S = 1.11	(Δ/σ)_max < 0.001
1957 reflections	Δρ_max = 0.16 e Å⁻³
212 parameters	Δρ_min = −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)

Crystal data top

C₂₂H₂₈O	V = 911.43 (4) Å³
M_r = 308.44	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 7.1577 (2) Å	µ = 0.07 mm⁻¹
b = 10.3456 (2) Å	T = 298 K
c = 12.3663 (3) Å	0.37 × 0.16 × 0.16 mm
β = 95.557 (1)°

Data collection top

Bruker X8 APEXII CCD area-detector diffractometer	1834 reflections with I > 2σ(I)
8379 measured reflections	R_int = 0.020
1957 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.102	H-atom parameters constrained
S = 1.11	Δρ_max = 0.16 e Å⁻³
1957 reflections	Δρ_min = −0.15 e Å⁻³
212 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+2, y+1/2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₈O
M_r	308.44
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	7.1577 (2), 10.3456 (2), 12.3663 (3)
β (°)	95.557 (1)
V (Å³)	911.43 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.37 × 0.16 × 0.16

Data collection
Diffractometer	Bruker X8 APEXII CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8379, 1957, 1834
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.102, 1.11
No. of reflections	1957
No. of parameters	212
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) −x+2, y+1/2, −z+2.

Acknowledgements

The authors thank the National Centre of Scientific and Technological Research (CNRST) for support.

References

Azoulay, P., Reynier, J. P., Balansard, G., Gasquet, M. & Timon-David, P. (1986). Pharm. Acta Helv. 61, 345–352. CAS PubMed Web of Science Google Scholar
Bohlmann, F., Czerson, H. & Schoneweib, S. (1977). Chem. Ber. 110, 1330–1334. CrossRef CAS Web of Science Google Scholar
Bohlmann, F. & Gupta, R. K. (1982). Phytochemistry, 21, 1443–1445. CrossRef CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ceccherelli, P., Curini, M. & Marcotullio, M. C. (1988). J. Nat. Prod. 51, 1006–1009. CrossRef CAS PubMed Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
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Kutney, J. P. & Singh, A. (1984). Can. J. Chem. 62, 1407–1409. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 67| Part 6| June 2011| Page o1381

doi:10.1107/S1600536811016941

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-(4a,8-Di­methyl-1,2,3,4,4a,5,6,8a-octa­hydro­naphthalen-2-yl)-3-(4-methyl­phen­yl)prop-2-en-1-one

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-(4a,8-Dimethyl-1,2,3,4,4a,5,6,8a-octahydronaphthalen-2-yl)-3-(4-methylphenyl)prop-2-en-1-one