(1S,2R,3S,6S,7R)-3,7,11,11-Tetra-methyl-6,7-epoxybi-cyclo-[5.4.0]undecane-2-ol.

The title compound, C15H26O2, was synthesized 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 Atlas cedar (cedrus atlantica). The mol-ecule is built up from a seven-membered ring to which a six- and a three-membered ring are fused. The seven- and six-membered rings each have a twist-boat conformation. In the crystal, O-H⋯O hydrogen bonds link the mol-ecules into zigzag chains running along the b-axis direction.

Related literature

For background to β-himachalene, see: El Haib et al.;(2011 ▶). For the reactivity of this sesquiterpene and its derivatives, see: El Jamili et al. (2002 ▶); Benharref et al. (2013 ▶); Ourhriss et al. (2013 ▶). For their potential anti­fungal activity against the phytopathogen Botrytis cinerea, see: Daoubi et al. (2004 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C15H26O2

M = 238.36

Monoclinic,

a = 5.9617 (10) Å

b = 12.068 (2) Å

c = 9.5909 (15) Å

β = 95.789 (8)°

V = 686.48 (19) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 298 K

0.38 × 0.11 × 0.10 mm

Data collection

Bruker X8 APEX diffractometer

11541 measured reflections

3036 independent reflections

2698 reflections with I > 2σ(I)

R int = 0.031

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.131

S = 1.06

3036 reflections

162 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.34 e Å−3

Δρmin = −0.16 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 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814008642/bt6976sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814008642/bt6976Isup2.hkl

CCDC reference: 997713

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H26O2	F(000) = 264
Mr = 238.36	Dx = 1.153 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 3036 reflections
a = 5.9617 (10) Å	θ = 2.7–27.1°
b = 12.068 (2) Å	µ = 0.07 mm−1
c = 9.5909 (15) Å	T = 298 K
β = 95.789 (8)°	Needle, colourless
V = 686.48 (19) Å3	0.38 × 0.11 × 0.10 mm
Z = 2

Bruker X8 APEX diffractometer	2698 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
Graphite monochromator	θmax = 27.1°, θmin = 2.7°
φ and ω scans	h = −7→7
11541 measured reflections	k = −15→15
3036 independent reflections	l = −11→12

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.131	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0862P)2 + 0.0329P] where P = (Fo2 + 2Fc2)/3
3036 reflections	(Δ/σ)max < 0.001
162 parameters	Δρmax = 0.34 e Å−3
1 restraint	Δρmin = −0.16 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 > 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
C2	0.0588 (3)	0.50820 (14)	0.02419 (18)	0.0314 (4)
H2	0.1734	0.5611	0.0000	0.038*
C4	0.2591 (3)	0.37310 (19)	−0.11371 (19)	0.0453 (5)
H4A	0.3279	0.4210	−0.1786	0.054*
H4B	0.2399	0.3005	−0.1567	0.054*
C9	0.3831 (5)	0.3909 (3)	0.4739 (2)	0.0657 (7)
H9A	0.5201	0.3606	0.5226	0.079*
H9B	0.2942	0.4216	0.5439	0.079*
H11	−0.153 (4)	0.608 (2)	−0.012 (3)	0.051 (8)*
C1	0.1382 (3)	0.45493 (13)	0.16735 (17)	0.0289 (3)
H1	0.0019	0.4272	0.2047	0.035*
C3	0.0279 (3)	0.41938 (15)	−0.09006 (19)	0.0372 (4)
H3	−0.0630	0.3592	−0.0565	0.045*
C5	0.4180 (3)	0.36301 (17)	0.02114 (19)	0.0395 (4)
H5A	0.5132	0.2982	0.0162	0.047*
H5B	0.5143	0.4279	0.0323	0.047*
C6	0.2821 (3)	0.35300 (14)	0.14433 (17)	0.0304 (3)
C7	0.3361 (3)	0.27224 (16)	0.2586 (2)	0.0412 (4)
C8	0.2506 (4)	0.2968 (2)	0.3985 (2)	0.0545 (6)
H8A	0.2637	0.2308	0.4564	0.065*
H8B	0.0925	0.3170	0.3840	0.065*
C10	0.4472 (4)	0.4851 (2)	0.3774 (2)	0.0531 (6)
H10A	0.5572	0.4567	0.3186	0.064*
H10B	0.5204	0.5431	0.4355	0.064*
C11	0.2506 (3)	0.53852 (15)	0.28073 (19)	0.0372 (4)
C12	0.5456 (4)	0.2016 (2)	0.2643 (3)	0.0612 (6)
H12A	0.5204	0.1334	0.3119	0.092*
H12B	0.6694	0.2405	0.3140	0.092*
H12C	0.5803	0.1859	0.1708	0.092*
C13	−0.0927 (4)	0.4641 (2)	−0.2266 (2)	0.0575 (6)
H13A	−0.0141	0.5281	−0.2558	0.086*
H13B	−0.2443	0.4842	−0.2120	0.086*
H13C	−0.0954	0.4080	−0.2977	0.086*
C14	0.3584 (4)	0.64005 (19)	0.2140 (3)	0.0574 (6)
H14A	0.2429	0.6824	0.1611	0.086*
H14B	0.4661	0.6150	0.1529	0.086*
H14C	0.4329	0.6856	0.2865	0.086*
C15	0.0719 (4)	0.5824 (2)	0.3696 (3)	0.0636 (7)
H15A	0.1416	0.6300	0.4416	0.095*
H15B	0.0005	0.5214	0.4118	0.095*
H15C	−0.0391	0.6235	0.3113	0.095*
O1	−0.1435 (2)	0.56718 (13)	0.04280 (17)	0.0465 (4)
O2	0.1605 (2)	0.24617 (10)	0.14695 (15)	0.0414 (3)

	U11	U22	U33	U12	U13	U23
C2	0.0338 (8)	0.0274 (8)	0.0338 (9)	−0.0005 (7)	0.0068 (6)	0.0023 (7)
C4	0.0540 (11)	0.0512 (12)	0.0321 (9)	0.0069 (9)	0.0119 (8)	−0.0066 (8)
C9	0.0770 (16)	0.0825 (18)	0.0347 (11)	0.0019 (14)	−0.0090 (10)	0.0007 (12)
C1	0.0297 (7)	0.0277 (7)	0.0300 (8)	−0.0025 (6)	0.0062 (6)	−0.0001 (6)
C3	0.0429 (10)	0.0379 (9)	0.0304 (9)	−0.0010 (7)	0.0020 (7)	−0.0009 (7)
C5	0.0379 (9)	0.0398 (9)	0.0419 (10)	0.0050 (8)	0.0100 (7)	−0.0051 (8)
C6	0.0321 (7)	0.0265 (7)	0.0317 (8)	−0.0036 (6)	−0.0003 (6)	−0.0027 (7)
C7	0.0462 (10)	0.0351 (10)	0.0403 (10)	−0.0033 (8)	−0.0060 (8)	0.0039 (8)
C8	0.0599 (13)	0.0623 (14)	0.0407 (11)	−0.0036 (11)	0.0022 (9)	0.0197 (10)
C10	0.0487 (11)	0.0572 (14)	0.0514 (13)	−0.0088 (9)	−0.0045 (9)	−0.0138 (10)
C11	0.0398 (9)	0.0374 (9)	0.0347 (9)	−0.0056 (7)	0.0052 (7)	−0.0098 (7)
C12	0.0595 (14)	0.0520 (13)	0.0681 (15)	0.0150 (11)	−0.0130 (11)	0.0080 (11)
C13	0.0698 (14)	0.0646 (14)	0.0352 (11)	0.0089 (12)	−0.0088 (9)	−0.0009 (10)
C14	0.0689 (14)	0.0398 (11)	0.0640 (14)	−0.0125 (11)	0.0086 (11)	−0.0075 (10)
C15	0.0596 (13)	0.0766 (17)	0.0561 (14)	0.0007 (12)	0.0141 (11)	−0.0262 (13)
O1	0.0504 (8)	0.0417 (8)	0.0490 (9)	0.0166 (6)	0.0121 (6)	0.0105 (7)
O2	0.0490 (8)	0.0270 (6)	0.0459 (7)	−0.0068 (5)	−0.0067 (6)	0.0019 (6)

C2—O1	1.427 (2)	C7—C12	1.508 (3)
C2—C3	1.531 (2)	C7—C8	1.512 (3)
C2—C1	1.546 (2)	C8—H8A	0.9700
C2—H2	0.9800	C8—H8B	0.9700
C4—C3	1.526 (3)	C10—C11	1.558 (3)
C4—C5	1.529 (3)	C10—H10A	0.9700
C4—H4A	0.9700	C10—H10B	0.9700
C4—H4B	0.9700	C11—C15	1.525 (3)
C9—C8	1.523 (4)	C11—C14	1.552 (3)
C9—C10	1.539 (4)	C12—H12A	0.9600
C9—H9A	0.9700	C12—H12B	0.9600
C9—H9B	0.9700	C12—H12C	0.9600
C1—C6	1.528 (2)	C13—H13A	0.9600
C1—C11	1.582 (2)	C13—H13B	0.9600
C1—H1	0.9800	C13—H13C	0.9600
C3—C13	1.527 (3)	C14—H14A	0.9600
C3—H3	0.9800	C14—H14B	0.9600
C5—C6	1.503 (2)	C14—H14C	0.9600
C5—H5A	0.9700	C15—H15A	0.9600
C5—H5B	0.9700	C15—H15B	0.9600
C6—C7	1.478 (3)	C15—H15C	0.9600
C6—O2	1.481 (2)	O1—H11	0.72 (3)
C7—O2	1.455 (2)
O1—C2—C3	113.36 (15)	C6—C7—C8	117.44 (17)
O1—C2—C1	106.45 (14)	C12—C7—C8	115.52 (19)
C3—C2—C1	110.40 (13)	C7—C8—C9	111.26 (19)
O1—C2—H2	108.8	C7—C8—H8A	109.4
C3—C2—H2	108.8	C9—C8—H8A	109.4
C1—C2—H2	108.8	C7—C8—H8B	109.4
C3—C4—C5	113.30 (14)	C9—C8—H8B	109.4
C3—C4—H4A	108.9	H8A—C8—H8B	108.0
C5—C4—H4A	108.9	C9—C10—C11	116.50 (19)
C3—C4—H4B	108.9	C9—C10—H10A	108.2
C5—C4—H4B	108.9	C11—C10—H10A	108.2
H4A—C4—H4B	107.7	C9—C10—H10B	108.2
C8—C9—C10	114.41 (18)	C11—C10—H10B	108.2
C8—C9—H9A	108.7	H10A—C10—H10B	107.3
C10—C9—H9A	108.7	C15—C11—C14	107.35 (18)
C8—C9—H9B	108.7	C15—C11—C10	109.69 (18)
C10—C9—H9B	108.7	C14—C11—C10	104.72 (17)
H9A—C9—H9B	107.6	C15—C11—C1	109.53 (15)
C6—C1—C2	109.41 (13)	C14—C11—C1	112.59 (15)
C6—C1—C11	114.05 (14)	C10—C11—C1	112.74 (15)
C2—C1—C11	114.57 (14)	C7—C12—H12A	109.5
C6—C1—H1	106.0	C7—C12—H12B	109.5
C2—C1—H1	106.0	H12A—C12—H12B	109.5
C11—C1—H1	106.0	C7—C12—H12C	109.5
C4—C3—C13	110.86 (16)	H12A—C12—H12C	109.5
C4—C3—C2	108.51 (15)	H12B—C12—H12C	109.5
C13—C3—C2	112.26 (17)	C3—C13—H13A	109.5
C4—C3—H3	108.4	C3—C13—H13B	109.5
C13—C3—H3	108.4	H13A—C13—H13B	109.5
C2—C3—H3	108.4	C3—C13—H13C	109.5
C6—C5—C4	109.51 (14)	H13A—C13—H13C	109.5
C6—C5—H5A	109.8	H13B—C13—H13C	109.5
C4—C5—H5A	109.8	C11—C14—H14A	109.5
C6—C5—H5B	109.8	C11—C14—H14B	109.5
C4—C5—H5B	109.8	H14A—C14—H14B	109.5
H5A—C5—H5B	108.2	C11—C14—H14C	109.5
C7—C6—O2	58.92 (11)	H14A—C14—H14C	109.5
C7—C6—C5	122.77 (16)	H14B—C14—H14C	109.5
O2—C6—C5	112.77 (14)	C11—C15—H15A	109.5
C7—C6—C1	120.48 (15)	C11—C15—H15B	109.5
O2—C6—C1	114.54 (12)	H15A—C15—H15B	109.5
C5—C6—C1	113.81 (14)	C11—C15—H15C	109.5
O2—C7—C6	60.64 (11)	H15A—C15—H15C	109.5
O2—C7—C12	115.87 (18)	H15B—C15—H15C	109.5
C6—C7—C12	121.17 (19)	C2—O1—H11	105 (2)
O2—C7—C8	114.42 (17)	C7—O2—C6	60.45 (11)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H11···O2i	0.72 (3)	2.11 (3)	2.820 (2)	171 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H11⋯O2i	0.72 (3)	2.11 (3)	2.820 (2)	171 (3)

Symmetry code: (i) .