3-(4-Chloro-phen-yl)-1-[(2R,4aR,8aR)-4a,8-dimethyl-1,2,3,4,4a,5,6,8a-octa-hydro-naphthalen-2-yl]prop-2-en-1-one.

The title compound, C(21)H(25)ClO, was semi-synthesized from isocostic acid, 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.

Related literature

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

Experimental

Crystal data

C21H25ClO

M = 328.86

Monoclinic,

a = 10.9869 (5) Å

b = 7.0054 (3) Å

c = 12.1883 (6) Å

β = 105.726 (2)°

V = 902.99 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.21 mm−1

T = 298 K

0.28 × 0.20 × 0.16 mm

Data collection

Bruker X8 APEX CCD area-detector diffractometer

6963 measured reflections

3358 independent reflections

2713 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.08

3358 reflections

210 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1373 Friedel pairs

Flack parameter: −0.11 (7)

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/S1600536811016886/ci5186sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811016886/ci5186Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811016886/ci5186Isup3.cml

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

C21H25ClO	F(000) = 352
Mr = 328.86	Dx = 1.206 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3362 reflections
a = 10.9869 (5) Å	θ = 3.5–26.3°
b = 7.0054 (3) Å	µ = 0.21 mm−1
c = 12.1883 (6) Å	T = 298 K
β = 105.726 (2)°	Prism, colourless
V = 902.99 (7) Å3	0.28 × 0.20 × 0.16 mm
Z = 2

Bruker X8 APEX CCD area-detector diffractometer	2713 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.021
graphite	θmax = 26.3°, θmin = 4.1°
Detector resolution: 8.3333 pixels mm-1	h = −13→13
ω and φ scans	k = −7→8
6963 measured reflections	l = −15→14
3358 independent reflections

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) = 0.106	w = 1/[σ2(Fo2) + (0.0579P)2] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max = 0.001
3358 reflections	Δρmax = 0.18 e Å−3
210 parameters	Δρmin = −0.21 e Å−3
1 restraint	Absolute structure: Flack (1983), 1373 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.11 (7)

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.

	x	y	z	Uiso*/Ueq
C1	−0.12078 (19)	0.1716 (3)	0.28143 (17)	0.0460 (5)
H1A	−0.1945	0.2468	0.2826	0.055*
H1B	−0.0877	0.1149	0.3562	0.055*
C2	−0.02074 (18)	0.3009 (3)	0.25507 (16)	0.0436 (5)
H2	0.0531	0.2209	0.2575	0.052*
C3	−0.06528 (19)	0.3826 (3)	0.13502 (16)	0.0481 (5)
H3A	0.0022	0.4573	0.1189	0.058*
H3B	−0.1368	0.4666	0.1299	0.058*
C4	−0.1039 (2)	0.2228 (3)	0.04658 (17)	0.0508 (5)
H4A	−0.0302	0.1463	0.0471	0.061*
H4B	−0.1347	0.2790	−0.0286	0.061*
C4A	−0.20679 (16)	0.0933 (3)	0.06975 (15)	0.0413 (4)
C5	−0.2281 (2)	−0.0790 (3)	−0.01062 (18)	0.0519 (5)
H5A	−0.2520	−0.0344	−0.0889	0.062*
H5B	−0.1495	−0.1495	0.0015	0.062*
C6	−0.3304 (2)	−0.2119 (3)	0.00779 (19)	0.0600 (6)
H6A	−0.4126	−0.1619	−0.0326	0.072*
H6B	−0.3210	−0.3363	−0.0239	0.072*
C7	−0.3245 (2)	−0.2335 (3)	0.13080 (19)	0.0555 (6)
H7	−0.3772	−0.3241	0.1498	0.067*
C8	−0.25005 (18)	−0.1339 (3)	0.21527 (17)	0.0466 (5)
C8A	−0.15912 (16)	0.0137 (3)	0.19227 (16)	0.0407 (4)
H8A	−0.0811	−0.0559	0.1945	0.049*
C9	0.02262 (19)	0.4566 (3)	0.34237 (17)	0.0480 (5)
C10	0.12607 (19)	0.5813 (3)	0.32607 (18)	0.0526 (5)
H10	0.1705	0.5438	0.2747	0.063*
C11	0.1570 (2)	0.7435 (3)	0.38210 (17)	0.0502 (5)
H11	0.1146	0.7733	0.4363	0.060*
C12	0.25209 (19)	0.8815 (3)	0.36696 (17)	0.0458 (5)
C13	0.3308 (2)	0.8509 (4)	0.2960 (2)	0.0618 (6)
H13	0.3262	0.7353	0.2575	0.074*
C14	0.4147 (2)	0.9871 (4)	0.2817 (2)	0.0669 (7)
H14	0.4662	0.9643	0.2338	0.080*
C15	0.4221 (2)	1.1572 (3)	0.33870 (19)	0.0570 (6)
C16	0.3477 (2)	1.1907 (3)	0.4105 (2)	0.0597 (6)
H16	0.3543	1.3056	0.4499	0.072*
C17	0.2636 (2)	1.0548 (3)	0.42400 (18)	0.0540 (5)
H17	0.2131	1.0790	0.4725	0.065*
C18	−0.2510 (2)	−0.1670 (4)	0.33701 (18)	0.0668 (6)
H18A	−0.3116	−0.2645	0.3397	0.100*
H18B	−0.2736	−0.0508	0.3684	0.100*
H18C	−0.1685	−0.2069	0.3807	0.100*
C19	−0.3293 (2)	0.2045 (3)	0.05233 (19)	0.0544 (5)
H19A	−0.3572	0.2478	−0.0252	0.082*
H19B	−0.3155	0.3124	0.1027	0.082*
H19C	−0.3928	0.1234	0.0685	0.082*
O	−0.02456 (15)	0.4817 (2)	0.42008 (13)	0.0666 (5)
Cl1	0.52589 (7)	1.33272 (12)	0.31822 (6)	0.0916 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0503 (11)	0.0493 (11)	0.0398 (10)	−0.0030 (9)	0.0149 (9)	0.0080 (9)
C2	0.0450 (10)	0.0452 (12)	0.0426 (10)	−0.0024 (8)	0.0150 (9)	−0.0013 (9)
C3	0.0563 (12)	0.0474 (12)	0.0456 (11)	−0.0116 (9)	0.0222 (9)	0.0044 (9)
C4	0.0547 (12)	0.0623 (14)	0.0407 (11)	−0.0130 (10)	0.0217 (10)	−0.0005 (10)
C4A	0.0398 (9)	0.0441 (10)	0.0415 (10)	−0.0028 (8)	0.0135 (8)	0.0041 (9)
C5	0.0533 (12)	0.0609 (13)	0.0450 (11)	−0.0084 (10)	0.0191 (9)	−0.0081 (10)
C6	0.0604 (13)	0.0575 (14)	0.0615 (14)	−0.0153 (11)	0.0156 (11)	−0.0047 (11)
C7	0.0553 (13)	0.0488 (12)	0.0659 (14)	−0.0105 (10)	0.0223 (11)	0.0054 (11)
C8	0.0482 (11)	0.0431 (11)	0.0505 (11)	0.0023 (9)	0.0169 (9)	0.0100 (9)
C8A	0.0385 (9)	0.0427 (11)	0.0416 (10)	0.0035 (8)	0.0122 (8)	0.0063 (8)
C9	0.0547 (12)	0.0482 (11)	0.0429 (11)	−0.0026 (9)	0.0163 (9)	0.0002 (9)
C10	0.0555 (12)	0.0524 (12)	0.0526 (12)	−0.0058 (10)	0.0193 (10)	−0.0099 (10)
C11	0.0567 (12)	0.0539 (13)	0.0418 (11)	0.0009 (10)	0.0163 (10)	−0.0046 (10)
C12	0.0492 (11)	0.0479 (12)	0.0399 (10)	−0.0019 (9)	0.0113 (9)	−0.0046 (9)
C13	0.0684 (14)	0.0576 (13)	0.0655 (14)	−0.0105 (12)	0.0286 (12)	−0.0241 (12)
C14	0.0655 (14)	0.0746 (16)	0.0695 (15)	−0.0161 (13)	0.0337 (12)	−0.0237 (14)
C15	0.0542 (12)	0.0655 (14)	0.0520 (13)	−0.0140 (11)	0.0157 (10)	−0.0074 (11)
C16	0.0713 (15)	0.0500 (13)	0.0571 (13)	−0.0074 (11)	0.0160 (12)	−0.0165 (11)
C17	0.0615 (13)	0.0556 (13)	0.0493 (12)	−0.0027 (11)	0.0225 (10)	−0.0105 (10)
C18	0.0787 (16)	0.0653 (14)	0.0586 (13)	−0.0192 (13)	0.0222 (12)	0.0195 (13)
C19	0.0495 (12)	0.0541 (13)	0.0560 (13)	0.0075 (10)	0.0083 (10)	0.0123 (10)
O	0.0877 (11)	0.0676 (10)	0.0527 (9)	−0.0183 (9)	0.0331 (8)	−0.0118 (8)
Cl1	0.0968 (5)	0.0864 (5)	0.0996 (5)	−0.0428 (4)	0.0405 (4)	−0.0190 (4)

C1—C2	1.524 (2)	C8—C8A	1.516 (3)
C1—C8A	1.527 (3)	C8A—H8A	0.98
C1—H1A	0.97	C9—O	1.209 (2)
C1—H1B	0.97	C9—C10	1.489 (3)
C2—C9	1.508 (3)	C10—C11	1.322 (3)
C2—C3	1.523 (3)	C10—H10	0.93
C2—H2	0.98	C11—C12	1.471 (3)
C3—C4	1.532 (3)	C11—H11	0.93
C3—H3A	0.97	C12—C17	1.388 (3)
C3—H3B	0.97	C12—C13	1.395 (3)
C4—C4A	1.534 (2)	C13—C14	1.370 (3)
C4—H4A	0.97	C13—H13	0.93
C4—H4B	0.97	C14—C15	1.371 (3)
C4A—C19	1.520 (3)	C14—H14	0.93
C4A—C5	1.532 (3)	C15—C16	1.370 (3)
C4A—C8A	1.546 (2)	C15—Cl1	1.740 (2)
C5—C6	1.522 (3)	C16—C17	1.367 (3)
C5—H5A	0.97	C16—H16	0.93
C5—H5B	0.97	C17—H17	0.93
C6—C7	1.491 (3)	C18—H18A	0.96
C6—H6A	0.97	C18—H18B	0.96
C6—H6B	0.97	C18—H18C	0.96
C7—C8	1.326 (3)	C19—H19A	0.96
C7—H7	0.93	C19—H19B	0.96
C8—C18	1.505 (3)	C19—H19C	0.96
C2—C1—C8A	110.86 (15)	C18—C8—C8A	117.95 (18)
C2—C1—H1A	109.5	C8—C8A—C1	115.52 (16)
C8A—C1—H1A	109.5	C8—C8A—C4A	110.91 (15)
C2—C1—H1B	109.5	C1—C8A—C4A	112.44 (15)
C8A—C1—H1B	109.5	C8—C8A—H8A	105.7
H1A—C1—H1B	108.1	C1—C8A—H8A	105.7
C9—C2—C3	111.35 (16)	C4A—C8A—H8A	105.7
C9—C2—C1	112.90 (16)	O—C9—C10	121.57 (19)
C3—C2—C1	111.31 (15)	O—C9—C2	122.51 (18)
C9—C2—H2	107.0	C10—C9—C2	115.91 (18)
C3—C2—H2	107.0	C11—C10—C9	122.3 (2)
C1—C2—H2	107.0	C11—C10—H10	118.8
C2—C3—C4	110.94 (16)	C9—C10—H10	118.8
C2—C3—H3A	109.5	C10—C11—C12	126.3 (2)
C4—C3—H3A	109.5	C10—C11—H11	116.8
C2—C3—H3B	109.5	C12—C11—H11	116.8
C4—C3—H3B	109.5	C17—C12—C13	117.22 (19)
H3A—C3—H3B	108.0	C17—C12—C11	118.91 (19)
C3—C4—C4A	112.32 (15)	C13—C12—C11	123.86 (18)
C3—C4—H4A	109.1	C14—C13—C12	121.5 (2)
C4A—C4—H4A	109.1	C14—C13—H13	119.2
C3—C4—H4B	109.1	C12—C13—H13	119.2
C4A—C4—H4B	109.1	C13—C14—C15	119.4 (2)
H4A—C4—H4B	107.9	C13—C14—H14	120.3
C19—C4A—C5	109.79 (16)	C15—C14—H14	120.3
C19—C4A—C4	109.90 (17)	C16—C15—C14	120.6 (2)
C5—C4A—C4	109.92 (15)	C16—C15—Cl1	119.90 (18)
C19—C4A—C8A	112.03 (15)	C14—C15—Cl1	119.51 (18)
C5—C4A—C8A	106.63 (16)	C17—C16—C15	119.8 (2)
C4—C4A—C8A	108.51 (15)	C17—C16—H16	120.1
C6—C5—C4A	112.23 (16)	C15—C16—H16	120.1
C6—C5—H5A	109.2	C16—C17—C12	121.4 (2)
C4A—C5—H5A	109.2	C16—C17—H17	119.3
C6—C5—H5B	109.2	C12—C17—H17	119.3
C4A—C5—H5B	109.2	C8—C18—H18A	109.5
H5A—C5—H5B	107.9	C8—C18—H18B	109.5
C7—C6—C5	112.20 (18)	H18A—C18—H18B	109.5
C7—C6—H6A	109.2	C8—C18—H18C	109.5
C5—C6—H6A	109.2	H18A—C18—H18C	109.5
C7—C6—H6B	109.2	H18B—C18—H18C	109.5
C5—C6—H6B	109.2	C4A—C19—H19A	109.5
H6A—C6—H6B	107.9	C4A—C19—H19B	109.5
C8—C7—C6	125.22 (19)	H19A—C19—H19B	109.5
C8—C7—H7	117.4	C4A—C19—H19C	109.5
C6—C7—H7	117.4	H19A—C19—H19C	109.5
C7—C8—C18	121.11 (19)	H19B—C19—H19C	109.5
C7—C8—C8A	120.92 (18)