3-[4-(Dimethyl-amino)-phen-yl]-1-(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(23)H(31)NO, was semisynthesized 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. The dihedral angle between the latter ring and its substituent is 83.6 (7)°.

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 ▶); Bohlmann et al. (1977 ▶); Ceccherelli et al. (1988 ▶). For the synthesis, see: Kutney & Singh (1984 ▶). For conformational analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H31NO

M = 337.49

Monoclinic,

a = 6.0593 (4) Å

b = 7.2095 (7) Å

c = 21.8937 (19) Å

β = 91.860 (7)°

V = 955.91 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.6 × 0.25 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini ultra diffractometer

8394 measured reflections

2112 independent reflections

1894 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.089

S = 1.05

2112 reflections

230 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.15 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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/S160053681005333X/fj2378sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681005333X/fj2378Isup2.hkl

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

C23H31NO	F(000) = 368
Mr = 337.49	Dx = 1.173 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 4058 reflections
a = 6.0593 (4) Å	θ = 3.0–28.5°
b = 7.2095 (7) Å	µ = 0.07 mm−1
c = 21.8937 (19) Å	T = 298 K
β = 91.860 (7)°	Prism, colourless
V = 955.91 (14) Å3	0.6 × 0.25 × 0.10 mm
Z = 2

Oxford Diffraction Xcalibur Eos Gemini ultra diffractometer	1894 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
graphite	θmax = 26.4°, θmin = 3.0°
Detector resolution: 16.1978 pixels mm-1	h = −7→7
φ and ω scans	k = −9→7
8394 measured reflections	l = −27→27
2112 independent reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.056P)2 + 0.0652P] where P = (Fo2 + 2Fc2)/3
2112 reflections	(Δ/σ)max = 0.002
230 parameters	Δρmax = 0.21 e Å−3
1 restraint	Δρmin = −0.15 e Å−3

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
C1	0.7303 (3)	0.8137 (3)	1.01854 (8)	0.0250 (4)
C2	0.9300 (3)	0.7287 (3)	1.00424 (8)	0.0278 (4)
H2	1.0181	0.6768	1.0353	0.033*
C3	0.9978 (3)	0.7208 (3)	0.94506 (8)	0.0280 (4)
H3	1.1328	0.6656	0.9373	0.034*
C4	0.8718 (3)	0.7923 (2)	0.89613 (8)	0.0263 (4)
C5	0.6725 (3)	0.8750 (3)	0.91030 (8)	0.0287 (4)
H5	0.5835	0.9236	0.8788	0.034*
C6	0.6025 (3)	0.8873 (3)	0.96950 (8)	0.0281 (4)
H6	0.4689	0.9450	0.9771	0.034*
C7	0.9359 (3)	0.7711 (3)	0.83304 (8)	0.0295 (4)
H7	0.8257	0.7832	0.8027	0.035*
C8	1.1400 (3)	0.7357 (3)	0.81514 (9)	0.0345 (4)
H8	1.2509	0.7321	0.8455	0.041*
C9	1.2066 (3)	0.7020 (3)	0.75226 (9)	0.0371 (5)
C10	1.0332 (3)	0.6566 (3)	0.70325 (8)	0.0321 (4)
H10	0.9057	0.7376	0.7089	0.038*
C11	1.1144 (4)	0.6858 (3)	0.63863 (9)	0.0422 (5)
H11A	1.1362	0.8174	0.6317	0.051*
H11B	1.2556	0.6244	0.6348	0.051*
C12	0.9521 (4)	0.6105 (3)	0.59038 (8)	0.0407 (5)
H12A	0.8182	0.6843	0.5905	0.049*
H12B	1.0155	0.6235	0.5505	0.049*
C13	0.8930 (3)	0.4083 (3)	0.60040 (8)	0.0299 (4)
C14	0.7155 (3)	0.3441 (4)	0.55361 (8)	0.0396 (5)
H14A	0.5853	0.4212	0.5571	0.048*
H14B	0.7699	0.3597	0.5127	0.048*
C15	0.6526 (3)	0.1432 (4)	0.56287 (9)	0.0458 (6)
H15A	0.5140	0.1185	0.5410	0.055*
H15B	0.7646	0.0643	0.5457	0.055*
C16	0.6295 (3)	0.0958 (3)	0.62862 (9)	0.0408 (5)
H16	0.5651	−0.0174	0.6379	0.049*
C17	0.6948 (3)	0.2044 (3)	0.67505 (8)	0.0317 (4)
C18	0.7946 (3)	0.3924 (3)	0.66407 (7)	0.0265 (4)
H18	0.6723	0.4812	0.6646	0.032*
C19	0.9605 (3)	0.4550 (3)	0.71385 (8)	0.0290 (4)
H19A	1.0886	0.3744	0.7140	0.035*
H19B	0.8940	0.4452	0.7534	0.035*
C20	1.0979 (3)	0.2867 (3)	0.59410 (9)	0.0393 (5)
H20A	1.0624	0.1607	0.6040	0.059*
H20B	1.2134	0.3303	0.6215	0.059*
H20C	1.1466	0.2929	0.5529	0.059*
C21	0.6499 (4)	0.1524 (4)	0.73956 (10)	0.0524 (6)
H21A	0.5633	0.0409	0.7399	0.079*
H21B	0.5703	0.2508	0.7586	0.079*
H21C	0.7871	0.1321	0.7617	0.079*
C22	0.8030 (3)	0.7487 (3)	1.12674 (9)	0.0393 (5)
H22A	0.8180	0.6174	1.1209	0.059*
H22B	0.7360	0.7719	1.1651	0.059*
H22C	0.9462	0.8058	1.1267	0.059*
C23	0.4516 (3)	0.8908 (3)	1.09306 (9)	0.0374 (5)
H23A	0.3430	0.7989	1.0819	0.056*
H23B	0.4199	1.0037	1.0712	0.056*
H23C	0.4482	0.9137	1.1362	0.056*
N1	0.6663 (2)	0.8252 (2)	1.07791 (7)	0.0325 (4)
O1	1.4040 (2)	0.6982 (3)	0.74180 (8)	0.0544 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0224 (7)	0.0172 (9)	0.0354 (8)	−0.0036 (7)	−0.0016 (6)	−0.0015 (7)
C2	0.0252 (8)	0.0228 (10)	0.0352 (9)	0.0016 (8)	−0.0042 (7)	0.0000 (8)
C3	0.0235 (7)	0.0214 (10)	0.0389 (9)	0.0023 (7)	0.0001 (7)	−0.0031 (8)
C4	0.0273 (8)	0.0171 (10)	0.0342 (9)	−0.0033 (7)	−0.0014 (7)	−0.0016 (7)
C5	0.0267 (8)	0.0229 (10)	0.0361 (9)	−0.0011 (7)	−0.0059 (7)	0.0015 (8)
C6	0.0230 (7)	0.0206 (9)	0.0406 (10)	0.0026 (7)	−0.0027 (7)	−0.0002 (8)
C7	0.0353 (9)	0.0189 (10)	0.0339 (9)	−0.0044 (7)	−0.0025 (7)	−0.0009 (7)
C8	0.0334 (9)	0.0317 (11)	0.0382 (10)	−0.0077 (9)	−0.0016 (7)	−0.0066 (8)
C9	0.0374 (9)	0.0279 (11)	0.0463 (11)	−0.0089 (9)	0.0073 (8)	−0.0057 (9)
C10	0.0379 (9)	0.0269 (11)	0.0318 (9)	−0.0051 (8)	0.0072 (7)	−0.0005 (8)
C11	0.0544 (12)	0.0335 (12)	0.0396 (10)	−0.0104 (10)	0.0152 (9)	0.0056 (9)
C12	0.0547 (11)	0.0415 (13)	0.0267 (9)	0.0020 (10)	0.0115 (8)	0.0086 (9)
C13	0.0314 (8)	0.0349 (11)	0.0237 (8)	0.0046 (8)	0.0054 (7)	−0.0005 (8)
C14	0.0383 (10)	0.0566 (15)	0.0239 (8)	0.0093 (10)	0.0009 (7)	−0.0053 (9)
C15	0.0403 (11)	0.0575 (15)	0.0395 (10)	−0.0011 (11)	−0.0006 (8)	−0.0215 (10)
C16	0.0335 (9)	0.0391 (13)	0.0499 (11)	−0.0039 (9)	0.0004 (8)	−0.0091 (10)
C17	0.0278 (8)	0.0328 (11)	0.0346 (9)	−0.0028 (8)	0.0021 (7)	−0.0024 (8)
C18	0.0271 (8)	0.0292 (10)	0.0233 (8)	0.0029 (8)	0.0036 (6)	−0.0010 (7)
C19	0.0349 (9)	0.0278 (10)	0.0244 (8)	−0.0059 (8)	0.0027 (7)	0.0008 (7)
C20	0.0306 (9)	0.0467 (14)	0.0410 (10)	0.0038 (9)	0.0069 (8)	−0.0074 (9)
C21	0.0661 (14)	0.0480 (15)	0.0433 (11)	−0.0277 (13)	0.0041 (10)	0.0073 (11)
C22	0.0369 (9)	0.0459 (14)	0.0350 (9)	0.0075 (10)	0.0017 (7)	0.0030 (9)
C23	0.0329 (9)	0.0344 (11)	0.0452 (11)	0.0081 (9)	0.0050 (8)	−0.0013 (9)
N1	0.0264 (7)	0.0366 (10)	0.0347 (8)	0.0037 (7)	0.0020 (6)	0.0032 (7)
O1	0.0352 (7)	0.0667 (12)	0.0619 (9)	−0.0137 (8)	0.0125 (7)	−0.0192 (9)

C1—N1	1.371 (2)	C13—C18	1.538 (2)
C1—C2	1.401 (2)	C14—C15	1.513 (4)
C1—C6	1.407 (2)	C14—H14A	0.9700
C2—C3	1.373 (2)	C14—H14B	0.9700
C2—H2	0.9300	C15—C16	1.490 (3)
C3—C4	1.394 (2)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—C5	1.390 (2)	C16—C17	1.333 (3)
C4—C7	1.455 (2)	C16—H16	0.9300
C5—C6	1.380 (2)	C17—C21	1.495 (3)
C5—H5	0.9300	C17—C18	1.507 (3)
C6—H6	0.9300	C18—C19	1.527 (2)
C7—C8	1.334 (3)	C18—H18	0.9800
C7—H7	0.9300	C19—H19A	0.9700
C8—C9	1.467 (3)	C19—H19B	0.9700
C8—H8	0.9300	C20—H20A	0.9600
C9—O1	1.226 (2)	C20—H20B	0.9600
C9—C10	1.513 (3)	C20—H20C	0.9600
C10—C11	1.527 (2)	C21—H21A	0.9600
C10—C19	1.538 (3)	C21—H21B	0.9600
C10—H10	0.9800	C21—H21C	0.9600
C11—C12	1.520 (3)	C22—N1	1.441 (2)
C11—H11A	0.9700	C22—H22A	0.9600
C11—H11B	0.9700	C22—H22B	0.9600
C12—C13	1.519 (3)	C22—H22C	0.9600
C12—H12A	0.9700	C23—N1	1.433 (2)
C12—H12B	0.9700	C23—H23A	0.9600
C13—C20	1.530 (3)	C23—H23B	0.9600
C13—C14	1.533 (2)	C23—H23C	0.9600
N1—C1—C2	120.75 (15)	C15—C14—H14B	109.2
N1—C1—C6	122.33 (15)	C13—C14—H14B	109.2
C2—C1—C6	116.91 (15)	H14A—C14—H14B	107.9
C3—C2—C1	121.08 (16)	C16—C15—C14	112.40 (17)
C3—C2—H2	119.5	C16—C15—H15A	109.1
C1—C2—H2	119.5	C14—C15—H15A	109.1
C2—C3—C4	122.42 (16)	C16—C15—H15B	109.1
C2—C3—H3	118.8	C14—C15—H15B	109.1
C4—C3—H3	118.8	H15A—C15—H15B	107.9
C5—C4—C3	116.43 (16)	C17—C16—C15	124.5 (2)
C5—C4—C7	121.17 (15)	C17—C16—H16	117.7
C3—C4—C7	122.26 (16)	C15—C16—H16	117.7
C6—C5—C4	122.21 (16)	C16—C17—C21	120.97 (19)
C6—C5—H5	118.9	C16—C17—C18	121.17 (17)
C4—C5—H5	118.9	C21—C17—C18	117.56 (17)
C5—C6—C1	120.93 (16)	C17—C18—C19	114.25 (15)
C5—C6—H6	119.5	C17—C18—C13	112.40 (15)
C1—C6—H6	119.5	C19—C18—C13	111.05 (13)
C8—C7—C4	125.31 (16)	C17—C18—H18	106.2
C8—C7—H7	117.3	C19—C18—H18	106.2
C4—C7—H7	117.3	C13—C18—H18	106.2
C7—C8—C9	126.40 (17)	C18—C19—C10	110.91 (16)
C7—C8—H8	116.8	C18—C19—H19A	109.5
C9—C8—H8	116.8	C10—C19—H19A	109.5
O1—C9—C8	118.61 (18)	C18—C19—H19B	109.5
O1—C9—C10	121.48 (17)	C10—C19—H19B	109.5
C8—C9—C10	119.69 (16)	H19A—C19—H19B	108.0
C9—C10—C11	112.96 (16)	C13—C20—H20A	109.5
C9—C10—C19	107.05 (17)	C13—C20—H20B	109.5
C11—C10—C19	111.88 (16)	H20A—C20—H20B	109.5
C9—C10—H10	108.3	C13—C20—H20C	109.5
C11—C10—H10	108.3	H20A—C20—H20C	109.5
C19—C10—H10	108.3	H20B—C20—H20C	109.5
C12—C11—C10	111.96 (16)	C17—C21—H21A	109.5
C12—C11—H11A	109.2	C17—C21—H21B	109.5
C10—C11—H11A	109.2	H21A—C21—H21B	109.5
C12—C11—H11B	109.2	C17—C21—H21C	109.5
C10—C11—H11B	109.2	H21A—C21—H21C	109.5
H11A—C11—H11B	107.9	H21B—C21—H21C	109.5
C13—C12—C11	113.12 (17)	N1—C22—H22A	109.5
C13—C12—H12A	109.0	N1—C22—H22B	109.5
C11—C12—H12A	109.0	H22A—C22—H22B	109.5
C13—C12—H12B	109.0	N1—C22—H22C	109.5
C11—C12—H12B	109.0	H22A—C22—H22C	109.5
H12A—C12—H12B	107.8	H22B—C22—H22C	109.5
C12—C13—C20	109.95 (17)	N1—C23—H23A	109.5
C12—C13—C14	110.92 (17)	N1—C23—H23B	109.5
C20—C13—C14	108.71 (16)	H23A—C23—H23B	109.5
C12—C13—C18	107.62 (15)	N1—C23—H23C	109.5
C20—C13—C18	112.25 (15)	H23A—C23—H23C	109.5
C14—C13—C18	107.38 (14)	H23B—C23—H23C	109.5
C15—C14—C13	111.95 (18)	C1—N1—C23	121.75 (15)
C15—C14—H14A	109.2	C1—N1—C22	120.44 (15)
C13—C14—H14A	109.2	C23—N1—C22	117.33 (15)