Absolute configuration of (1R,3S,8R,11R)-3,7,7,10-tetra-methyl-tri-cyclo-[6.4.0.0(1,3)]dodec-9-en-11-ol.

The absolute configuration of the title compound, C16H26O, was determined as (1R,3S,8R,11R) based mainly on the synthetic pathway but is also implied by the X-ray analysis. The mol-ecule contains fused six- and seven-membered rings. Part of the seven-membered ring was refined as disordered over two sets of sites with the occupancy ratio fixed at 0.86:0.14. The disorder corresponds to a major chair conformation and a minor boat conforation. In the crysyal, O-H⋯O hydrogen bonds connect the mol-ecules into chains parallel to the a axis.

Related literature

For related structures, see: Benharref et al. (2010 ▶); Gassman & Goman (1990 ▶); Lassaba et al. (1997 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶); Boessenkool & Boyens (1980 ▶). For Bijvoet pair analysis, see: Hooft et al. (2008 ▶). For analysis of the absolute structure, see: Flack & Bernardinelli (2000 ▶). For chemical properties of related compounds, see: Paresh & Sujit (2012 ▶); Arfaoui et al. (2010 ▶). For their biol­ogical properties, see: Chung et al. (2007 ▶); Servi et al. (2000 ▶). For the synthesis, see: Auhmani et al. (2001 ▶).

Experimental

Crystal data

C16H26O

M = 234.37

Orthorhombic,

a = 6.1457 (1) Å

b = 8.2466 (2) Å

c = 27.4454 (7) Å

V = 1390.96 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.51 mm−1

T = 173 K

0.32 × 0.13 × 0.07 mm

Data collection

Agilent Xcalibur (Eos, Gemini ultra) diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.863, T max = 1.000

8172 measured reflections

2653 independent reflections

2539 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.098

S = 1.04

2653 reflections

190 parameters

29 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.17 e Å−3

Δρmin = −0.18 e Å−3

Absolute structure: Flack (1983 ▶) 1059 Friedel pairs

Flack parameter: −0.1 (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: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, New_Global_Publ_Block. DOI: 10.1107/S1600536813018497/lh5626sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813018497/lh5626Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813018497/lh5626Isup3.cml

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

C16H26O	F(000) = 520
Mr = 234.37	Dx = 1.119 Mg m−3
Orthorhombic, P212121	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: P 2ac 2ab	Cell parameters from 4275 reflections
a = 6.1457 (1) Å	θ = 4.8–70.8°
b = 8.2466 (2) Å	µ = 0.51 mm−1
c = 27.4454 (7) Å	T = 173 K
V = 1390.96 (5) Å3	Flattened, colourless
Z = 4	0.32 × 0.13 × 0.07 mm

Agilent Xcalibur (Eos, Gemini ultra) diffractometer	2653 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	2539 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.027
Detector resolution: 16.1978 pixels mm-1	θmax = 70.9°, θmin = 5.6°
ω scans	h = −4→7
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −10→10
Tmin = 0.863, Tmax = 1.000	l = −33→33
8172 measured reflections

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0565P)2 + 0.1685P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max = 0.001
2653 reflections	Δρmax = 0.17 e Å−3
190 parameters	Δρmin = −0.18 e Å−3
29 restraints	Absolute structure: Flack (1983) 1059 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.1 (3)

Experimental. Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. CrysAlisPro (Agilent Technologies,2012)

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 > 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	Occ. (<1)
C1	0.1547 (2)	0.65315 (18)	0.60903 (5)	0.0280 (3)
C2	0.2298 (3)	0.82761 (18)	0.60418 (6)	0.0343 (3)
H2A	0.3882	0.8490	0.6054	0.041*
H2B	0.1469	0.8995	0.5821	0.041*
C3	0.1203 (3)	0.7732 (2)	0.65035 (6)	0.0355 (4)
C4	0.2612 (3)	0.7567 (2)	0.69559 (6)	0.0429 (4)
H4A	0.2338	0.8509	0.7171	0.051*
H4B	0.4159	0.7607	0.6856	0.051*
C5	0.2235 (4)	0.6023 (3)	0.72468 (6)	0.0529 (5)	0.86
H51	0.0668	0.5749	0.7238	0.064*	0.86
H52	0.2641	0.6219	0.7591	0.064*	0.86
C6	0.3564 (4)	0.4560 (3)	0.70501 (7)	0.0466 (5)	0.86
H61	0.5115	0.4883	0.7036	0.056*	0.86
H62	0.3446	0.3664	0.7289	0.056*	0.86
C7	0.2906 (3)	0.3898 (2)	0.65441 (6)	0.0385 (4)
C14	0.0619 (4)	0.3224 (3)	0.65551 (8)	0.0472 (5)	0.86
H14A	0.0520	0.2379	0.6805	0.071*	0.86
H14B	0.0264	0.2758	0.6236	0.071*	0.86
H14C	−0.0409	0.4096	0.6631	0.071*	0.86
C15	0.4476 (4)	0.2429 (3)	0.64537 (9)	0.0511 (5)	0.86
H15A	0.4348	0.1657	0.6723	0.077*	0.86
H15B	0.5978	0.2822	0.6433	0.077*	0.86
H15C	0.4082	0.1892	0.6148	0.077*	0.86
C5A	0.2235 (4)	0.6023 (3)	0.72468 (6)	0.0529 (5)	0.14
H5A1	0.1299	0.6267	0.7531	0.064*	0.14
H5A2	0.3646	0.5614	0.7370	0.064*	0.14
C6A	0.1122 (19)	0.4674 (14)	0.6926 (3)	0.042 (3)	0.14
H6A1	−0.0105	0.5151	0.6741	0.050*	0.14
H6A2	0.0537	0.3808	0.7138	0.050*	0.14
C14A	0.157 (2)	0.2487 (14)	0.6310 (4)	0.044 (3)	0.14
H14D	0.2386	0.2024	0.6037	0.066*	0.14
H14E	0.0173	0.2908	0.6192	0.066*	0.14
H14F	0.1302	0.1645	0.6555	0.066*	0.14
C15A	0.481 (2)	0.347 (2)	0.6806 (6)	0.057 (4)	0.14
H15D	0.4468	0.2601	0.7038	0.086*	0.14
H15E	0.5358	0.4415	0.6983	0.086*	0.14
H15F	0.5928	0.3086	0.6578	0.086*	0.14
C8	0.3284 (2)	0.52177 (18)	0.61381 (5)	0.0282 (3)
H8	0.4651	0.5796	0.6232	0.034*
C9	0.3722 (2)	0.44966 (18)	0.56417 (5)	0.0308 (3)
H9	0.4993	0.3849	0.5610	0.037*
C10	0.2508 (2)	0.46765 (18)	0.52450 (5)	0.0307 (3)
C11	0.0428 (3)	0.56358 (18)	0.52503 (5)	0.0331 (3)
H11	−0.0731	0.4988	0.5084	0.040*
C12	−0.0336 (2)	0.6044 (2)	0.57649 (5)	0.0314 (3)
H12A	−0.1401	0.6944	0.5750	0.038*
H12B	−0.1078	0.5089	0.5907	0.038*
C13	−0.1071 (3)	0.8335 (3)	0.66163 (7)	0.0502 (5)
H13A	−0.0981	0.9378	0.6786	0.075*
H13B	−0.1820	0.7545	0.6824	0.075*
H13C	−0.1883	0.8473	0.6312	0.075*
C16	0.3177 (3)	0.3995 (2)	0.47569 (6)	0.0427 (4)
H16A	0.4620	0.3497	0.4785	0.064*
H16B	0.3227	0.4870	0.4516	0.064*
H16C	0.2120	0.3175	0.4653	0.064*
O1	0.0853 (2)	0.70648 (14)	0.49657 (4)	0.0435 (3)
H1	−0.046 (2)	0.748 (3)	0.4920 (9)	0.065*

	U11	U22	U33	U12	U13	U23
C1	0.0236 (6)	0.0359 (7)	0.0246 (6)	−0.0037 (6)	0.0019 (5)	−0.0029 (6)
C2	0.0342 (7)	0.0337 (7)	0.0349 (7)	−0.0034 (6)	0.0026 (6)	−0.0042 (6)
C3	0.0302 (8)	0.0441 (8)	0.0322 (7)	−0.0030 (7)	0.0042 (6)	−0.0092 (7)
C4	0.0392 (9)	0.0586 (10)	0.0308 (8)	−0.0090 (8)	0.0017 (7)	−0.0121 (7)
C5	0.0572 (11)	0.0760 (13)	0.0256 (7)	−0.0117 (11)	0.0014 (7)	−0.0029 (8)
C6	0.0424 (10)	0.0666 (13)	0.0309 (9)	−0.0071 (11)	−0.0070 (8)	0.0113 (9)
C7	0.0376 (8)	0.0450 (8)	0.0330 (8)	−0.0065 (7)	−0.0021 (6)	0.0080 (7)
C14	0.0421 (10)	0.0557 (12)	0.0436 (11)	−0.0167 (10)	−0.0012 (9)	0.0160 (10)
C15	0.0506 (12)	0.0486 (11)	0.0541 (12)	0.0052 (10)	−0.0055 (10)	0.0171 (10)
C5A	0.0572 (11)	0.0760 (13)	0.0256 (7)	−0.0117 (11)	0.0014 (7)	−0.0029 (8)
C6A	0.051 (7)	0.052 (6)	0.022 (4)	0.000 (6)	0.001 (5)	0.005 (5)
C14A	0.058 (8)	0.041 (6)	0.033 (5)	−0.004 (6)	0.007 (6)	−0.003 (5)
C15A	0.040 (7)	0.065 (9)	0.067 (9)	0.012 (7)	−0.012 (6)	0.010 (7)
C8	0.0222 (6)	0.0355 (7)	0.0269 (7)	−0.0048 (6)	−0.0010 (5)	0.0006 (6)
C9	0.0274 (7)	0.0309 (7)	0.0340 (7)	−0.0005 (6)	0.0040 (6)	−0.0008 (6)
C10	0.0362 (7)	0.0285 (7)	0.0274 (7)	−0.0073 (6)	0.0030 (6)	−0.0025 (6)
C11	0.0335 (7)	0.0388 (8)	0.0269 (7)	−0.0068 (6)	−0.0057 (6)	−0.0010 (6)
C12	0.0226 (6)	0.0411 (8)	0.0305 (7)	−0.0026 (6)	−0.0016 (6)	−0.0002 (6)
C13	0.0388 (9)	0.0636 (11)	0.0481 (10)	0.0056 (9)	0.0103 (8)	−0.0153 (9)
C16	0.0561 (10)	0.0394 (8)	0.0327 (8)	−0.0079 (8)	0.0061 (7)	−0.0080 (7)
O1	0.0504 (7)	0.0459 (7)	0.0343 (5)	0.0059 (5)	−0.0022 (5)	0.0083 (5)

C1—C12	1.516 (2)	C15—H15B	0.9800
C1—C2	1.517 (2)	C15—H15C	0.9800
C1—C3	1.520 (2)	C6A—H6A1	0.9900
C1—C8	1.527 (2)	C6A—H6A2	0.9900
C2—C3	1.503 (2)	C14A—H14D	0.9800
C2—H2A	0.9900	C14A—H14E	0.9800
C2—H2B	0.9900	C14A—H14F	0.9800
C3—C13	1.515 (2)	C15A—H15D	0.9800
C3—C4	1.520 (2)	C15A—H15E	0.9800
C4—C5	1.521 (3)	C15A—H15F	0.9800
C4—H4A	0.9900	C8—C9	1.5106 (19)
C4—H4B	0.9900	C8—H8	1.0000
C5—C6	1.553 (3)	C9—C10	1.328 (2)
C5—H51	0.9900	C9—H9	0.9500
C5—H52	0.9900	C10—C11	1.503 (2)
C6—C7	1.546 (2)	C10—C16	1.510 (2)
C6—H61	0.9900	C11—O1	1.4378 (19)
C6—H62	0.9900	C11—C12	1.526 (2)
C7—C15A	1.421 (11)	C11—H11	1.0000
C7—C14	1.512 (3)	C12—H12A	0.9900
C7—C14A	1.563 (11)	C12—H12B	0.9900
C7—C15	1.568 (3)	C13—H13A	0.9800
C7—C8	1.575 (2)	C13—H13B	0.9800
C7—C6A	1.646 (10)	C13—H13C	0.9800
C14—H14A	0.9800	C16—H16A	0.9800
C14—H14B	0.9800	C16—H16B	0.9800
C14—H14C	0.9800	C16—H16C	0.9800
C15—H15A	0.9800	O1—H1	0.887 (11)
C12—C1—C2	115.60 (13)	C7—C14—H14B	109.5
C12—C1—C3	120.38 (13)	C7—C14—H14C	109.5
C2—C1—C3	59.34 (10)	C7—C15—H15A	109.5
C12—C1—C8	113.34 (12)	C7—C15—H15B	109.5
C2—C1—C8	117.89 (12)	C7—C15—H15C	109.5
C3—C1—C8	119.71 (12)	C7—C6A—H6A1	109.7
C3—C2—C1	60.45 (10)	C7—C6A—H6A2	109.7
C3—C2—H2A	117.7	H6A1—C6A—H6A2	108.2
C1—C2—H2A	117.7	C7—C14A—H14D	109.5
C3—C2—H2B	117.7	C7—C14A—H14E	109.5
C1—C2—H2B	117.7	H14D—C14A—H14E	109.5
H2A—C2—H2B	114.8	C7—C14A—H14F	109.5
C2—C3—C13	119.16 (15)	H14D—C14A—H14F	109.5
C2—C3—C4	117.39 (14)	H14E—C14A—H14F	109.5
C13—C3—C4	112.84 (14)	C7—C15A—H15D	109.5
C2—C3—C1	60.21 (9)	C7—C15A—H15E	109.5
C13—C3—C1	119.64 (14)	H15D—C15A—H15E	109.5
C4—C3—C1	118.13 (14)	C7—C15A—H15F	109.5
C3—C4—C5	114.67 (15)	H15D—C15A—H15F	109.5
C3—C4—H4A	108.6	H15E—C15A—H15F	109.5
C5—C4—H4A	108.6	C9—C8—C1	109.06 (11)
C3—C4—H4B	108.6	C9—C8—C7	113.10 (13)
C5—C4—H4B	108.6	C1—C8—C7	116.61 (12)
H4A—C4—H4B	107.6	C9—C8—H8	105.7
C4—C5—C6	112.81 (15)	C1—C8—H8	105.7
C4—C5—H51	109.0	C7—C8—H8	105.7
C6—C5—H51	109.0	C10—C9—C8	126.54 (14)
C4—C5—H52	109.0	C10—C9—H9	116.7
C6—C5—H52	109.0	C8—C9—H9	116.7
H51—C5—H52	107.8	C9—C10—C11	121.90 (13)
C7—C6—C5	116.67 (17)	C9—C10—C16	122.19 (15)
C7—C6—H61	108.1	C11—C10—C16	115.87 (14)
C5—C6—H61	108.1	O1—C11—C10	105.75 (12)
C7—C6—H62	108.1	O1—C11—C12	112.20 (13)
C5—C6—H62	108.1	C10—C11—C12	112.76 (12)
H61—C6—H62	107.3	O1—C11—H11	108.7
C15A—C7—C14	131.7 (7)	C10—C11—H11	108.7
C15A—C7—C6	54.4 (7)	C12—C11—H11	108.7
C14—C7—C6	110.81 (16)	C1—C12—C11	111.64 (12)
C15A—C7—C14A	117.1 (9)	C1—C12—H12A	109.3
C6—C7—C14A	140.3 (5)	C11—C12—H12A	109.3
C15A—C7—C15	51.6 (7)	C1—C12—H12B	109.3
C14—C7—C15	106.92 (17)	C11—C12—H12B	109.3
C6—C7—C15	104.71 (16)	H12A—C12—H12B	108.0
C14A—C7—C15	71.6 (6)	C3—C13—H13A	109.5
C15A—C7—C8	114.2 (7)	C3—C13—H13B	109.5
C14—C7—C8	113.93 (14)	H13A—C13—H13B	109.5
C6—C7—C8	110.66 (14)	C3—C13—H13C	109.5
C14A—C7—C8	107.6 (5)	H13A—C13—H13C	109.5
C15—C7—C8	109.33 (14)	H13B—C13—H13C	109.5
C15A—C7—C6A	108.9 (8)	C10—C16—H16A	109.5
C14—C7—C6A	60.7 (4)	C10—C16—H16B	109.5
C6—C7—C6A	57.7 (4)	H16A—C16—H16B	109.5
C14A—C7—C6A	101.5 (7)	C10—C16—H16C	109.5
C15—C7—C6A	144.2 (4)	H16A—C16—H16C	109.5
C8—C7—C6A	106.2 (4)	H16B—C16—H16C	109.5
C7—C14—H14A	109.5	C11—O1—H1	103.2 (18)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O1i	0.89 (1)	2.32 (1)	3.1612 (6)	159 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯O1i	0.89 (1)	2.32 (1)	3.1612 (6)	159 (2)

Symmetry code: (i) .