(1S,3S,8R,9S,10R)-9,10-Ep-oxy-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodeca-ne.

The title compound, C16H26O, was synthesized by treating (1S,3S,8R)-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-ene with meta-chloro-perbenzoic acid. The mol-ecule is built up from two fused six- and seven-membered rings. The six-membered ring has a half-chair conformation, whereas the seven-membered ring displays a boat conformation. In the crystal, there are no significant intermolecular interactions present.

Related literature

For the use of ep­oxy­des in organic synthesis, see: Mori (1989 ▶); Paddon-Jones et al. (1997 ▶); Taylor et al. (1991 ▶). For their biological activity, see: Kupchan et al. (1989 ▶); Trost et al. (1983 ▶); Vollhardt & Schore (1996 ▶); Yang (2004 ▶). For structural discussion, see: Cremer & Pople (1975 ▶); Flack (1983 ▶); Flack & Bernardinelli (2000 ▶); Spek (2009 ▶); Boessenkool & Boyens (1980 ▶); Benharref et al. (2010 ▶). For the synthesis, see: Auhmani et al. (2001 ▶).

Experimental

Crystal data

C16H26O

M = 234.37

Monoclinic,

a = 10.5563 (10) Å

b = 5.7548 (5) Å

c = 11.7096 (13) Å

β = 92.777 (8)°

V = 710.52 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.07 mm−1

T = 180 K

0.31 × 0.31 × 0.25 mm

Data collection

Agilent Xcalibur Eos Gemini ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.767, T max = 1.0

8241 measured reflections

2899 independent reflections

2150 reflections with I > 2σ(I)

R int = 0.055

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.105

S = 1.05

2899 reflections

158 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.14 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis PRO (Agilent, 2012 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: SHELXL2013.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536814006230/xu5778sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814006230/xu5778Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814006230/xu5778Isup3.cml

CCDC reference: 992783

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

C16H26O	F(000) = 260
Mr = 234.37	Dx = 1.095 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1871 reflections
a = 10.5563 (10) Å	θ = 3.9–26.5°
b = 5.7548 (5) Å	µ = 0.07 mm−1
c = 11.7096 (13) Å	T = 180 K
β = 92.777 (8)°	Box, colourless
V = 710.52 (12) Å3	0.31 × 0.31 × 0.25 mm
Z = 2

Agilent Xcalibur Eos Gemini ultra diffractometer	2899 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2150 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.055
Detector resolution: 16.1978 pixels mm-1	θmax = 26.4°, θmin = 3.5°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −7→7
Tmin = 0.767, Tmax = 1.0	l = −14→14
8241 measured reflections

Refinement on F2	1 restraint
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.054	H-atom parameters constrained
wR(F2) = 0.105	w = 1/[σ2(Fo2) + (0.0267P)2] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2899 reflections	Δρmax = 0.14 e Å−3
158 parameters	Δρmin = −0.21 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.

	x	y	z	Uiso*/Ueq
C1	0.2747 (3)	0.7760 (5)	0.3324 (3)	0.0241 (7)
C2	0.2251 (3)	0.6047 (6)	0.4168 (3)	0.0334 (8)
H2A	0.2213	0.4390	0.3941	0.040*
H2B	0.2461	0.6322	0.4990	0.040*
C3	0.1336 (3)	0.7699 (5)	0.3563 (3)	0.0276 (7)
C4	0.0457 (3)	0.6751 (6)	0.2618 (3)	0.0392 (9)
H4A	−0.0380	0.6418	0.2929	0.047*
H4B	0.0805	0.5271	0.2338	0.047*
C5	0.0281 (3)	0.8450 (7)	0.1615 (3)	0.0493 (11)
H5A	−0.0017	0.7571	0.0927	0.059*
H5B	−0.0391	0.9578	0.1791	0.059*
C6	0.1479 (3)	0.9792 (7)	0.1341 (3)	0.0429 (9)
H6A	0.1271	1.0768	0.0661	0.051*
H6B	0.1680	1.0860	0.1987	0.051*
C7	0.2684 (3)	0.8433 (6)	0.1112 (3)	0.0335 (8)
C8	0.3116 (3)	0.6867 (5)	0.2160 (3)	0.0265 (8)
H8	0.2675	0.5342	0.2043	0.032*
C9	0.4518 (3)	0.6354 (5)	0.2177 (3)	0.0295 (8)
H9	0.4857	0.5925	0.1423	0.035*
C10	0.5427 (3)	0.7440 (6)	0.2993 (3)	0.0289 (8)
C11	0.4987 (3)	0.9110 (5)	0.3879 (3)	0.0296 (8)
H11A	0.5481	1.0566	0.3826	0.036*
H11B	0.5182	0.8436	0.4645	0.036*
C12	0.3575 (3)	0.9715 (5)	0.3781 (3)	0.0274 (7)
H12A	0.3296	1.0162	0.4546	0.033*
H12B	0.3454	1.1078	0.3272	0.033*
C13	0.0746 (3)	0.9619 (6)	0.4244 (3)	0.0381 (9)
H13A	0.0582	1.0970	0.3750	0.057*
H13B	0.1328	1.0060	0.4885	0.057*
H13C	−0.0054	0.9069	0.4539	0.057*
C14	0.2449 (4)	0.6836 (8)	0.0066 (3)	0.0551 (11)
H14A	0.1789	0.5702	0.0227	0.083*
H14B	0.3235	0.6018	−0.0094	0.083*
H14C	0.2174	0.7774	−0.0599	0.083*
C15	0.3718 (3)	1.0198 (6)	0.0830 (3)	0.0460 (10)
H15A	0.3407	1.1195	0.0198	0.069*
H15B	0.4478	0.9367	0.0608	0.069*
H15C	0.3928	1.1157	0.1505	0.069*
C16	0.6798 (3)	0.7660 (7)	0.2706 (3)	0.0460 (10)
H16A	0.7340	0.7499	0.3406	0.069*
H16B	0.6939	0.9186	0.2363	0.069*
H16C	0.7007	0.6438	0.2164	0.069*
O1	0.50267 (19)	0.5041 (4)	0.31494 (19)	0.0350 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0183 (15)	0.0264 (17)	0.0278 (18)	−0.0012 (14)	0.0043 (13)	−0.0014 (15)
C2	0.0307 (19)	0.0345 (19)	0.035 (2)	0.0008 (16)	0.0051 (15)	0.0065 (16)
C3	0.0200 (16)	0.0298 (18)	0.0331 (19)	−0.0018 (15)	0.0035 (14)	0.0032 (16)
C4	0.0207 (18)	0.044 (2)	0.053 (3)	−0.0058 (16)	0.0012 (16)	−0.0024 (19)
C5	0.032 (2)	0.063 (3)	0.051 (3)	0.006 (2)	−0.0125 (18)	−0.001 (2)
C6	0.039 (2)	0.052 (2)	0.036 (2)	0.008 (2)	−0.0060 (16)	0.012 (2)
C7	0.036 (2)	0.040 (2)	0.0245 (19)	0.0031 (17)	−0.0014 (15)	0.0003 (16)
C8	0.0259 (18)	0.0267 (18)	0.0267 (19)	−0.0016 (14)	0.0000 (14)	−0.0050 (14)
C9	0.0309 (19)	0.0325 (19)	0.0254 (19)	0.0047 (16)	0.0049 (14)	0.0018 (16)
C10	0.0229 (17)	0.0339 (19)	0.0299 (19)	0.0008 (16)	0.0008 (14)	0.0046 (16)
C11	0.0251 (17)	0.034 (2)	0.0295 (19)	−0.0038 (14)	−0.0014 (14)	−0.0024 (15)
C12	0.0281 (18)	0.0302 (17)	0.0242 (18)	−0.0042 (16)	0.0028 (13)	−0.0060 (15)
C13	0.0273 (19)	0.036 (2)	0.052 (2)	0.0061 (16)	0.0123 (16)	−0.0024 (18)
C14	0.065 (3)	0.069 (3)	0.030 (2)	0.006 (2)	−0.0101 (19)	−0.010 (2)
C15	0.055 (2)	0.046 (2)	0.037 (2)	0.002 (2)	0.0087 (17)	0.0144 (18)
C16	0.0251 (19)	0.071 (3)	0.043 (2)	0.000 (2)	0.0038 (16)	−0.001 (2)
O1	0.0302 (13)	0.0314 (12)	0.0433 (15)	0.0050 (12)	0.0011 (10)	0.0018 (12)

C1—C12	1.507 (4)	C9—O1	1.448 (4)
C1—C2	1.508 (4)	C9—C10	1.462 (4)
C1—C8	1.525 (4)	C9—H9	1.0000
C1—C3	1.529 (4)	C10—O1	1.458 (4)
C2—C3	1.507 (4)	C10—C11	1.504 (4)
C2—H2A	0.9900	C10—C16	1.507 (4)
C2—H2B	0.9900	C11—C12	1.530 (4)
C3—C4	1.511 (5)	C11—H11A	0.9900
C3—C13	1.514 (4)	C11—H11B	0.9900
C4—C5	1.533 (5)	C12—H12A	0.9900
C4—H4A	0.9900	C12—H12B	0.9900
C4—H4B	0.9900	C13—H13A	0.9800
C5—C6	1.529 (5)	C13—H13B	0.9800
C5—H5A	0.9900	C13—H13C	0.9800
C5—H5B	0.9900	C14—H14A	0.9800
C6—C7	1.528 (4)	C14—H14B	0.9800
C6—H6A	0.9900	C14—H14C	0.9800
C6—H6B	0.9900	C15—H15A	0.9800
C7—C15	1.538 (5)	C15—H15B	0.9800
C7—C14	1.541 (5)	C15—H15C	0.9800
C7—C8	1.573 (4)	C16—H16A	0.9800
C8—C9	1.508 (4)	C16—H16B	0.9800
C8—H8	1.0000	C16—H16C	0.9800
C12—C1—C2	118.0 (3)	O1—C9—C8	116.1 (2)
C12—C1—C8	113.6 (2)	C10—C9—C8	122.5 (3)
C2—C1—C8	118.5 (3)	O1—C9—H9	115.5
C12—C1—C3	120.4 (2)	C10—C9—H9	115.5
C2—C1—C3	59.52 (19)	C8—C9—H9	115.5
C8—C1—C3	116.7 (3)	O1—C10—C9	59.45 (19)
C3—C2—C1	60.9 (2)	O1—C10—C11	114.7 (2)
C3—C2—H2A	117.7	C9—C10—C11	120.6 (3)
C1—C2—H2A	117.7	O1—C10—C16	113.3 (3)
C3—C2—H2B	117.7	C9—C10—C16	119.9 (3)
C1—C2—H2B	117.7	C11—C10—C16	115.6 (3)
H2A—C2—H2B	114.8	C10—C11—C12	115.2 (3)
C2—C3—C4	118.3 (3)	C10—C11—H11A	108.5
C2—C3—C13	118.9 (3)	C12—C11—H11A	108.5
C4—C3—C13	113.3 (3)	C10—C11—H11B	108.5
C2—C3—C1	59.5 (2)	C12—C11—H11B	108.5
C4—C3—C1	116.3 (3)	H11A—C11—H11B	107.5
C13—C3—C1	120.6 (3)	C1—C12—C11	113.8 (2)
C3—C4—C5	112.2 (3)	C1—C12—H12A	108.8
C3—C4—H4A	109.2	C11—C12—H12A	108.8
C5—C4—H4A	109.2	C1—C12—H12B	108.8
C3—C4—H4B	109.2	C11—C12—H12B	108.8
C5—C4—H4B	109.2	H12A—C12—H12B	107.7
H4A—C4—H4B	107.9	C3—C13—H13A	109.5
C6—C5—C4	114.3 (3)	C3—C13—H13B	109.5
C6—C5—H5A	108.7	H13A—C13—H13B	109.5
C4—C5—H5A	108.7	C3—C13—H13C	109.5
C6—C5—H5B	108.7	H13A—C13—H13C	109.5
C4—C5—H5B	108.7	H13B—C13—H13C	109.5
H5A—C5—H5B	107.6	C7—C14—H14A	109.5
C7—C6—C5	118.9 (3)	C7—C14—H14B	109.5
C7—C6—H6A	107.6	H14A—C14—H14B	109.5
C5—C6—H6A	107.6	C7—C14—H14C	109.5
C7—C6—H6B	107.6	H14A—C14—H14C	109.5
C5—C6—H6B	107.6	H14B—C14—H14C	109.5
H6A—C6—H6B	107.0	C7—C15—H15A	109.5
C6—C7—C15	107.8 (3)	C7—C15—H15B	109.5
C6—C7—C14	110.0 (3)	H15A—C15—H15B	109.5
C15—C7—C14	108.2 (3)	C7—C15—H15C	109.5
C6—C7—C8	111.6 (3)	H15A—C15—H15C	109.5
C15—C7—C8	111.3 (3)	H15B—C15—H15C	109.5
C14—C7—C8	107.9 (3)	C10—C16—H16A	109.5
C9—C8—C1	110.3 (3)	C10—C16—H16B	109.5
C9—C8—C7	111.7 (2)	H16A—C16—H16B	109.5
C1—C8—C7	115.3 (2)	C10—C16—H16C	109.5
C9—C8—H8	106.3	H16A—C16—H16C	109.5
C1—C8—H8	106.3	H16B—C16—H16C	109.5
C7—C8—H8	106.3	C9—O1—C10	60.41 (19)
O1—C9—C10	60.14 (19)