2-Acetyl-3,5,5,9-tetra-methyl-6,7,8,9-tetra-hydro-5H-benzocyclo-hepten-7-one.

The title compound, C(17)H(22)O(2), was semi-synthesized from a mixture of α-atlantone (Z) and α-atlantone (E), which were isolated from the essential oil of the Atlas cedar (cedrus atlantica). The mol-ecule consists of fused six- and seven-membered rings. The seven-membered ring is in a screw-boat conformation.

Related literature

For the isolation of α-atlantone (Z) and its isomer α-atlantone (E), see: Plattier & Teisseire (1974 ▶). For the reactivity of these ketones, see: Loughzail et al. (2009 ▶); Mazoir et al. (2009 ▶). For the isolation and reactivity of aryl-himachalene, see: Son Bredenberg & Erdtman (1961 ▶); Daunis et al. (1981 ▶) For puckerint parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H22O2

M = 258.35

Monoclinic,

a = 7.7996 (6) Å

b = 18.3702 (10) Å

c = 9.9357 (6) Å

β = 99.616 (7)°

V = 1403.59 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 180 K

0.6 × 0.25 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur Eos Gemini ultra diffractometer

14554 measured reflections

2855 independent reflections

2196 reflections with I > 2σ(I)

R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.145

S = 1.08

2855 reflections

177 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.29 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/S1600536810050610/lh5174sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050610/lh5174Isup2.hkl

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

C17H22O2	F(000) = 560
Mr = 258.35	Dx = 1.223 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2855 reflections
a = 7.7996 (6) Å	θ = 3.5–29.3°
b = 18.3702 (10) Å	µ = 0.08 mm−1
c = 9.9357 (6) Å	T = 180 K
β = 99.616 (7)°	Needle, colourless
V = 1403.59 (16) Å3	0.6 × 0.25 × 0.10 mm
Z = 4

Oxford Diffraction Xcalibur Eos Gemini ultra diffractometer	2196 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.054
graphite	θmax = 26.4°, θmin = 3.5°
Detector resolution: 16.1978 pixels mm-1	h = −9→9
φ and ω scans	k = −22→22
14554 measured reflections	l = −12→13
2855 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.145	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0729P)2 + 0.4506P] where P = (Fo2 + 2Fc2)/3
2855 reflections	(Δ/σ)max < 0.001
177 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

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
C1	0.3403 (2)	0.13187 (7)	0.19877 (15)	0.0192 (3)
C3	0.3247 (2)	0.09640 (8)	−0.04316 (15)	0.0205 (3)
C4	0.2676 (2)	0.02663 (8)	−0.01250 (15)	0.0204 (3)
C5	0.2523 (2)	0.01136 (8)	0.12259 (16)	0.0230 (3)
H5	0.2154	−0.0350	0.1424	0.028*
C6	0.2887 (2)	0.06101 (8)	0.23016 (15)	0.0217 (3)
C2	0.3584 (2)	0.14604 (8)	0.06319 (15)	0.0207 (3)
H2	0.3958	0.1922	0.0430	0.025*
C13	0.2253 (2)	−0.03137 (9)	−0.11877 (16)	0.0261 (4)
C14	0.1717 (2)	−0.10595 (9)	−0.07708 (18)	0.0298 (4)
H14C	0.1449	−0.1363	−0.1565	0.045*
H14B	0.0710	−0.1017	−0.0338	0.045*
H14A	0.2653	−0.1273	−0.0145	0.045*
C10	0.3481 (2)	0.18511 (9)	0.44504 (16)	0.0279 (4)
H10A	0.4307	0.1503	0.4920	0.034*
H10B	0.3653	0.2309	0.4940	0.034*
C11	0.3860 (2)	0.19632 (8)	0.29825 (16)	0.0244 (4)
C7	0.2791 (2)	0.03531 (9)	0.37574 (16)	0.0279 (4)
H7	0.3916	0.0462	0.4322	0.033*
C8	0.1391 (2)	0.07785 (9)	0.43676 (17)	0.0294 (4)
H13A	0.0269	0.0690	0.3805	0.035*
H13B	0.1342	0.0586	0.5270	0.035*
C12	0.3533 (3)	0.12064 (9)	−0.18269 (17)	0.0296 (4)
H12C	0.4006	0.1690	−0.1770	0.044*
H12B	0.2445	0.1203	−0.2443	0.044*
H12A	0.4332	0.0880	−0.2156	0.044*
C9	0.1675 (2)	0.15840 (9)	0.44834 (17)	0.0304 (4)
C15	0.2465 (3)	−0.04610 (9)	0.38933 (18)	0.0344 (4)
H15B	0.1345	−0.0583	0.3384	0.052*
H15A	0.2495	−0.0581	0.4838	0.052*
H15C	0.3349	−0.0731	0.3544	0.052*
C16	0.2815 (3)	0.26390 (9)	0.23925 (19)	0.0398 (5)
H16A	0.3121	0.2761	0.1523	0.060*
H16B	0.3081	0.3042	0.3008	0.060*
H16C	0.1593	0.2534	0.2280	0.060*
C17	0.5811 (3)	0.21235 (11)	0.3114 (2)	0.0401 (5)
H17A	0.6462	0.1694	0.3420	0.060*
H17B	0.6121	0.2509	0.3762	0.060*
H17C	0.6072	0.2268	0.2242	0.060*
O1	0.0495 (2)	0.19936 (8)	0.45978 (19)	0.0569 (5)
O2	0.2338 (2)	−0.01978 (7)	−0.23812 (13)	0.0451 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0204 (8)	0.0162 (6)	0.0213 (7)	0.0013 (6)	0.0047 (6)	−0.0012 (5)
C3	0.0206 (8)	0.0216 (7)	0.0201 (7)	0.0008 (6)	0.0053 (6)	0.0008 (6)
C4	0.0216 (8)	0.0197 (7)	0.0206 (7)	0.0009 (6)	0.0056 (6)	−0.0023 (6)
C5	0.0305 (9)	0.0162 (7)	0.0246 (8)	−0.0016 (6)	0.0110 (6)	−0.0008 (6)
C6	0.0284 (8)	0.0181 (7)	0.0207 (7)	−0.0003 (6)	0.0100 (6)	−0.0007 (6)
C2	0.0233 (8)	0.0158 (7)	0.0240 (8)	−0.0002 (6)	0.0065 (6)	0.0019 (5)
C13	0.0299 (9)	0.0236 (7)	0.0255 (8)	0.0000 (6)	0.0065 (7)	−0.0034 (6)
C14	0.0380 (10)	0.0216 (8)	0.0309 (9)	−0.0030 (7)	0.0088 (8)	−0.0075 (6)
C10	0.0407 (10)	0.0212 (7)	0.0209 (8)	0.0002 (7)	0.0023 (7)	−0.0041 (6)
C11	0.0336 (9)	0.0166 (7)	0.0231 (8)	−0.0007 (6)	0.0056 (7)	−0.0023 (6)
C7	0.0406 (10)	0.0226 (7)	0.0227 (8)	−0.0006 (7)	0.0118 (7)	−0.0004 (6)
C8	0.0383 (10)	0.0308 (9)	0.0215 (8)	−0.0040 (7)	0.0118 (7)	−0.0031 (6)
C12	0.0415 (10)	0.0265 (8)	0.0225 (8)	−0.0031 (7)	0.0104 (7)	0.0019 (6)
C9	0.0420 (11)	0.0297 (8)	0.0218 (8)	0.0067 (7)	0.0115 (7)	−0.0022 (6)
C15	0.0477 (11)	0.0278 (8)	0.0305 (9)	0.0021 (8)	0.0150 (8)	0.0045 (7)
C16	0.0705 (14)	0.0206 (8)	0.0293 (9)	0.0125 (8)	0.0109 (9)	−0.0009 (7)
C17	0.0399 (11)	0.0412 (10)	0.0392 (10)	−0.0167 (9)	0.0065 (8)	−0.0103 (8)
O1	0.0600 (10)	0.0397 (8)	0.0797 (12)	0.0175 (7)	0.0368 (9)	−0.0021 (7)
O2	0.0778 (11)	0.0364 (7)	0.0217 (6)	−0.0148 (7)	0.0099 (6)	−0.0065 (5)

C1—C2	1.402 (2)	C11—C17	1.534 (3)
C1—C6	1.412 (2)	C11—C16	1.546 (2)
C1—C11	1.545 (2)	C7—C15	1.527 (2)
C3—C2	1.387 (2)	C7—C8	1.547 (2)
C3—C4	1.407 (2)	C7—H7	0.9800
C3—C12	1.508 (2)	C8—C9	1.498 (2)
C4—C5	1.396 (2)	C8—H13A	0.9700
C4—C13	1.498 (2)	C8—H13B	0.9700
C5—C6	1.398 (2)	C12—H12C	0.9600
C5—H5	0.9300	C12—H12B	0.9600
C6—C7	1.535 (2)	C12—H12A	0.9600
C2—H2	0.9300	C9—O1	1.209 (2)
C13—O2	1.217 (2)	C15—H15B	0.9600
C13—C14	1.510 (2)	C15—H15A	0.9600
C14—H14C	0.9600	C15—H15C	0.9600
C14—H14B	0.9600	C16—H16A	0.9600
C14—H14A	0.9600	C16—H16B	0.9600
C10—C9	1.497 (3)	C16—H16C	0.9600
C10—C11	1.549 (2)	C17—H17A	0.9600
C10—H10A	0.9700	C17—H17B	0.9600
C10—H10B	0.9700	C17—H17C	0.9600
C2—C1—C6	117.47 (13)	C15—C7—C6	114.81 (13)
C2—C1—C11	115.01 (12)	C15—C7—C8	108.73 (14)
C6—C1—C11	127.49 (13)	C6—C7—C8	111.27 (13)
C2—C3—C4	117.42 (13)	C15—C7—H7	107.2
C2—C3—C12	117.90 (14)	C6—C7—H7	107.2
C4—C3—C12	124.68 (14)	C8—C7—H7	107.2
C5—C4—C3	118.18 (13)	C9—C8—C7	115.09 (14)
C5—C4—C13	119.40 (13)	C9—C8—H13A	108.5
C3—C4—C13	122.41 (13)	C7—C8—H13A	108.5
C4—C5—C6	124.41 (14)	C9—C8—H13B	108.5
C4—C5—H5	117.8	C7—C8—H13B	108.5
C6—C5—H5	117.8	H13A—C8—H13B	107.5
C5—C6—C1	117.48 (13)	C3—C12—H12C	109.5
C5—C6—C7	118.96 (13)	C3—C12—H12B	109.5
C1—C6—C7	123.50 (13)	H12C—C12—H12B	109.5
C3—C2—C1	124.97 (14)	C3—C12—H12A	109.5
C3—C2—H2	117.5	H12C—C12—H12A	109.5
C1—C2—H2	117.5	H12B—C12—H12A	109.5
O2—C13—C4	121.39 (15)	O1—C9—C10	122.13 (16)
O2—C13—C14	119.23 (14)	O1—C9—C8	121.14 (18)
C4—C13—C14	119.37 (14)	C10—C9—C8	116.73 (15)
C13—C14—H14C	109.5	C7—C15—H15B	109.5
C13—C14—H14B	109.5	C7—C15—H15A	109.5
H14C—C14—H14B	109.5	H15B—C15—H15A	109.5
C13—C14—H14A	109.5	C7—C15—H15C	109.5
H14C—C14—H14A	109.5	H15B—C15—H15C	109.5
H14B—C14—H14A	109.5	H15A—C15—H15C	109.5
C9—C10—C11	113.10 (14)	C11—C16—H16A	109.5
C9—C10—H10A	109.0	C11—C16—H16B	109.5
C11—C10—H10A	109.0	H16A—C16—H16B	109.5
C9—C10—H10B	109.0	C11—C16—H16C	109.5
C11—C10—H10B	109.0	H16A—C16—H16C	109.5
H10A—C10—H10B	107.8	H16B—C16—H16C	109.5
C17—C11—C1	108.73 (13)	C11—C17—H17A	109.5
C17—C11—C16	109.32 (15)	C11—C17—H17B	109.5
C1—C11—C16	108.79 (14)	H17A—C17—H17B	109.5
C17—C11—C10	106.74 (14)	C11—C17—H17C	109.5
C1—C11—C10	116.12 (12)	H17A—C17—H17C	109.5
C16—C11—C10	106.99 (13)	H17B—C17—H17C	109.5