(1S,3S,8R,10R,11R)-3,7,7,10-Tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodecan-11-ol.

The title compound, C16H28O, was synthesized by three steps from β-himachalene (3,5,5,9-tetra-methyl-2,4a,5,6,7,8-hexa-hydro-1H-benzo-cyclo-heptene), which was isolated from the essential oil of the Atlas cedar (Cedrus atlantica). The mol-ecule is built up from fused six- and seven-membered rings and an appended three-membered ring. The six-membered ring has twist-boat conformation, whereas the seven-membered ring displays a chair conformation. In the crystal, mol-ecules are linked into chains propagating along the a-axis direction by O-H⋯O hydrogen bonds.

Related literature

For the reactivity and biological properties of β-himachalene, see: Auhmani et al.(2002 ▶); El Jamili et al. (2002 ▶); Daoubi et al. (2004 ▶). For related structures, see: Ourhriss et al. (2013 ▶); Benharref et al. (2013 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C16H28O

M = 236.38

Orthorhombic,

a = 5.8796 (2) Å

b = 12.7822 (4) Å

c = 19.1496 (7) Å

V = 1439.17 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.25 × 0.15 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

8482 measured reflections

1724 independent reflections

1485 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.102

S = 1.03

1724 reflections

160 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813020576/bt6923sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813020576/bt6923Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813020576/bt6923Isup3.cml

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

C16H28O	F(000) = 528
Mr = 236.38	Dx = 1.091 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1724 reflections
a = 5.8796 (2) Å	θ = 2.7–26.4°
b = 12.7822 (4) Å	µ = 0.07 mm−1
c = 19.1496 (7) Å	T = 298 K
V = 1439.17 (8) Å3	Prism, colourless
Z = 4	0.25 × 0.15 × 0.10 mm

Bruker APEXII CCD diffractometer	1485 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
Graphite monochromator	θmax = 26.4°, θmin = 2.7°
ω and φ scans	h = −7→6
8482 measured reflections	k = −15→15
1724 independent reflections	l = −23→23

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)] = 0.038	H-atom parameters constrained
wR(F2) = 0.102	w = 1/[σ2(Fo2) + (0.0536P)2 + 0.1784P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
1724 reflections	Δρmax = 0.15 e Å−3
160 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.012 (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.

	x	y	z	Uiso*/Ueq
C1	0.8389 (3)	1.04007 (14)	0.11966 (10)	0.0381 (4)
C2	0.9711 (4)	1.13257 (15)	0.14824 (11)	0.0510 (5)
H2A	1.1339	1.1244	0.1544	0.061*
H2B	0.9231	1.2021	0.1342	0.061*
C3	0.8171 (4)	1.07206 (16)	0.19602 (11)	0.0467 (5)
C4	0.9300 (4)	1.00520 (18)	0.25137 (11)	0.0585 (6)
H4A	0.9184	1.0411	0.2958	0.070*
H4B	1.0904	0.9991	0.2402	0.070*
C5	0.8329 (5)	0.89612 (19)	0.25971 (11)	0.0612 (6)
H5A	0.6687	0.8995	0.2553	0.073*
H5B	0.8678	0.8707	0.3062	0.073*
C6	0.9253 (4)	0.81891 (16)	0.20627 (10)	0.0551 (6)
H6A	0.8718	0.7499	0.2194	0.066*
H6B	1.0896	0.8183	0.2108	0.066*
C7	0.8694 (3)	0.83462 (15)	0.12864 (10)	0.0413 (5)
C8	0.9669 (3)	0.93978 (13)	0.09937 (9)	0.0352 (4)
H8	1.1210	0.9467	0.1183	0.042*
C9	0.9916 (4)	0.93761 (14)	0.01895 (9)	0.0439 (4)
H9A	1.1288	0.8996	0.0068	0.053*
H9B	0.8634	0.9003	−0.0009	0.053*
C10	1.0027 (4)	1.04668 (16)	−0.01305 (10)	0.0489 (5)
H10	1.1151	1.0873	0.0133	0.059*
C11	0.7729 (4)	1.09873 (15)	−0.00364 (12)	0.0528 (6)
H11	0.6729	1.0760	−0.0417	0.063*
C12	0.6602 (4)	1.06999 (15)	0.06595 (11)	0.0464 (5)
H12A	0.5728	1.1291	0.0830	0.056*
H12B	0.5567	1.0118	0.0590	0.056*
C13	0.5996 (5)	1.1233 (2)	0.22183 (14)	0.0690 (7)
H13A	0.6296	1.1599	0.2646	0.104*
H13B	0.4863	1.0706	0.2298	0.104*
H13C	0.5456	1.1719	0.1874	0.104*
C14	0.6117 (4)	0.82570 (18)	0.11891 (13)	0.0562 (6)
H14A	0.5752	0.8317	0.0702	0.084*
H14B	0.5375	0.8807	0.1443	0.084*
H14C	0.5607	0.7591	0.1361	0.084*
C15	0.9811 (5)	0.74201 (14)	0.09077 (12)	0.0563 (6)
H15A	0.9325	0.6777	0.1119	0.084*
H15B	1.1435	0.7478	0.0942	0.084*
H15C	0.9371	0.7426	0.0425	0.084*
C16	1.0780 (6)	1.0442 (2)	−0.08917 (12)	0.0769 (8)
H16A	1.2321	1.0197	−0.0919	0.115*
H16B	1.0686	1.1134	−0.1085	0.115*
H16C	0.9807	0.9980	−0.1150	0.115*
O1	0.8089 (4)	1.20972 (12)	−0.01013 (12)	0.0789 (6)
H1	0.6857	1.2396	−0.0120	0.118*

	U11	U22	U33	U12	U13	U23
C1	0.0310 (9)	0.0379 (9)	0.0454 (10)	−0.0016 (8)	−0.0027 (9)	−0.0033 (8)
C2	0.0448 (12)	0.0457 (10)	0.0625 (13)	−0.0076 (10)	−0.0022 (11)	−0.0117 (9)
C3	0.0404 (11)	0.0495 (11)	0.0502 (11)	−0.0040 (10)	0.0018 (10)	−0.0143 (9)
C4	0.0555 (14)	0.0780 (15)	0.0419 (11)	−0.0040 (12)	−0.0058 (11)	−0.0128 (10)
C5	0.0680 (15)	0.0762 (15)	0.0394 (11)	−0.0016 (14)	0.0003 (12)	0.0067 (10)
C6	0.0609 (14)	0.0566 (12)	0.0478 (11)	0.0041 (11)	−0.0034 (11)	0.0126 (10)
C7	0.0406 (11)	0.0402 (9)	0.0431 (10)	−0.0007 (9)	−0.0014 (9)	0.0032 (8)
C8	0.0285 (9)	0.0394 (9)	0.0378 (9)	−0.0005 (8)	−0.0029 (8)	0.0002 (7)
C9	0.0476 (11)	0.0420 (9)	0.0419 (10)	0.0026 (9)	0.0028 (9)	−0.0010 (8)
C10	0.0540 (12)	0.0490 (11)	0.0435 (10)	−0.0043 (11)	−0.0007 (10)	0.0056 (9)
C11	0.0549 (13)	0.0448 (11)	0.0586 (12)	−0.0005 (10)	−0.0141 (11)	0.0099 (10)
C12	0.0375 (10)	0.0416 (10)	0.0603 (12)	0.0045 (9)	−0.0077 (10)	0.0004 (9)
C13	0.0592 (15)	0.0730 (16)	0.0748 (16)	0.0046 (14)	0.0130 (13)	−0.0234 (13)
C14	0.0478 (12)	0.0572 (13)	0.0635 (13)	−0.0135 (11)	−0.0021 (11)	0.0105 (11)
C15	0.0687 (16)	0.0371 (10)	0.0632 (13)	0.0014 (11)	0.0020 (13)	0.0016 (9)
C16	0.100 (2)	0.0785 (16)	0.0527 (13)	0.0024 (17)	0.0111 (15)	0.0157 (12)
O1	0.0872 (13)	0.0459 (8)	0.1035 (14)	0.0081 (9)	0.0012 (13)	0.0243 (9)

C1—C2	1.517 (3)	C9—H9A	0.9700
C1—C12	1.519 (3)	C9—H9B	0.9700
C1—C3	1.524 (3)	C10—C11	1.517 (3)
C1—C8	1.536 (2)	C10—C16	1.524 (3)
C2—C3	1.502 (3)	C10—H10	0.9800
C2—H2A	0.9700	C11—O1	1.440 (2)
C2—H2B	0.9700	C11—C12	1.533 (3)
C3—C4	1.515 (3)	C11—H11	0.9800
C3—C13	1.520 (3)	C12—H12A	0.9700
C4—C5	1.515 (3)	C12—H12B	0.9700
C4—H4A	0.9700	C13—H13A	0.9600
C4—H4B	0.9700	C13—H13B	0.9600
C5—C6	1.522 (3)	C13—H13C	0.9600
C5—H5A	0.9700	C14—H14A	0.9600
C5—H5B	0.9700	C14—H14B	0.9600
C6—C7	1.536 (3)	C14—H14C	0.9600
C6—H6A	0.9700	C15—H15A	0.9600
C6—H6B	0.9700	C15—H15B	0.9600
C7—C14	1.531 (3)	C15—H15C	0.9600
C7—C15	1.536 (3)	C16—H16A	0.9600
C7—C8	1.565 (2)	C16—H16B	0.9600
C8—C9	1.547 (2)	C16—H16C	0.9600
C8—H8	0.9800	O1—H1	0.8200
C9—C10	1.524 (3)
C2—C1—C12	113.73 (16)	C10—C9—H9A	109.0
C2—C1—C3	59.18 (13)	C8—C9—H9A	109.0
C12—C1—C3	121.59 (17)	C10—C9—H9B	109.0
C2—C1—C8	119.38 (16)	C8—C9—H9B	109.0
C12—C1—C8	112.19 (15)	H9A—C9—H9B	107.8
C3—C1—C8	120.51 (16)	C11—C10—C16	112.4 (2)
C3—C2—C1	60.63 (13)	C11—C10—C9	108.36 (18)
C3—C2—H2A	117.7	C16—C10—C9	112.22 (18)
C1—C2—H2A	117.7	C11—C10—H10	107.9
C3—C2—H2B	117.7	C16—C10—H10	107.9
C1—C2—H2B	117.7	C9—C10—H10	107.9
H2A—C2—H2B	114.8	O1—C11—C10	106.89 (19)
C2—C3—C4	116.9 (2)	O1—C11—C12	112.0 (2)
C2—C3—C13	118.91 (19)	C10—C11—C12	112.53 (17)
C4—C3—C13	112.6 (2)	O1—C11—H11	108.4
C2—C3—C1	60.18 (12)	C10—C11—H11	108.4
C4—C3—C1	118.90 (17)	C12—C11—H11	108.4
C13—C3—C1	119.91 (19)	C1—C12—C11	110.48 (17)
C3—C4—C5	115.3 (2)	C1—C12—H12A	109.6
C3—C4—H4A	108.4	C11—C12—H12A	109.6
C5—C4—H4A	108.4	C1—C12—H12B	109.6
C3—C4—H4B	108.4	C11—C12—H12B	109.6
C5—C4—H4B	108.4	H12A—C12—H12B	108.1
H4A—C4—H4B	107.5	C3—C13—H13A	109.5
C4—C5—C6	113.0 (2)	C3—C13—H13B	109.5
C4—C5—H5A	109.0	H13A—C13—H13B	109.5
C6—C5—H5A	109.0	C3—C13—H13C	109.5
C4—C5—H5B	109.0	H13A—C13—H13C	109.5
C6—C5—H5B	109.0	H13B—C13—H13C	109.5
H5A—C5—H5B	107.8	C7—C14—H14A	109.5
C5—C6—C7	119.33 (18)	C7—C14—H14B	109.5
C5—C6—H6A	107.5	H14A—C14—H14B	109.5
C7—C6—H6A	107.5	C7—C14—H14C	109.5
C5—C6—H6B	107.5	H14A—C14—H14C	109.5
C7—C6—H6B	107.5	H14B—C14—H14C	109.5
H6A—C6—H6B	107.0	C7—C15—H15A	109.5
C14—C7—C6	108.64 (19)	C7—C15—H15B	109.5
C14—C7—C15	108.0 (2)	H15A—C15—H15B	109.5
C6—C7—C15	105.37 (16)	C7—C15—H15C	109.5
C14—C7—C8	112.51 (17)	H15A—C15—H15C	109.5
C6—C7—C8	112.38 (16)	H15B—C15—H15C	109.5
C15—C7—C8	109.65 (16)	C10—C16—H16A	109.5
C1—C8—C9	108.22 (15)	C10—C16—H16B	109.5
C1—C8—C7	116.53 (15)	H16A—C16—H16B	109.5
C9—C8—C7	112.05 (14)	C10—C16—H16C	109.5
C1—C8—H8	106.5	H16A—C16—H16C	109.5
C9—C8—H8	106.5	H16B—C16—H16C	109.5
C7—C8—H8	106.5	C11—O1—H1	109.5
C10—C9—C8	112.81 (15)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1i	0.82	2.35	3.139 (3)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1i	0.82	2.35	3.139 (3)	163

Symmetry code: (i) .