2,6-Di­methyl-3-methyl­enebi­cyclo­[3.2.1]­octane-2,8-diol

The title compound, C₁₁H₁₈O₂, is a natural product mimic containing five chiral centres.

Key indicators

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.046
• wR factor = 0.123
• Data-to-parameter ratio = 18.4

checkCIF results

No syntax errors found

ADDSYM reports no extra symmetry


 Alert Level C:



PLAT_031  Alert C Refined Extinction parameter within range ....       2.75 Sigma


 0 Alert Level A = Potentially serious problem

 0 Alert Level B = Potential problem

 1 Alert Level C = Please check

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Computing details

Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO an COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1990).

(I)

Crystal data

C11H18O2	F(000) = 400
Mr = 182.25	Dx = 1.206 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.8216 (14) Å	Cell parameters from 5108 reflections
b = 18.934 (4) Å	θ = 2.9–30.5°
c = 8.1610 (16) Å	µ = 0.08 mm^−1
β = 107.76 (3)°	T = 150 K
V = 1003.9 (3) Å^3	Needle, colourless
Z = 4	0.4 × 0.05 × 0.05 mm

Data collection

Nonius KappaCCD area-detector diffractometer	1447 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.058
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	θmax = 27.5°, θmin = 3.3°
Tmin = 0.968, Tmax = 0.996	h = −8→8
7926 measured reflections	k = −23→24
2262 independent reflections	l = −9→10

Refinement

Refinement on F^2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0649P)^2]
R[F^2 > 2σ(F^2)] = 0.046	(Δ/σ)max = 0.01
wR(F^2) = 0.123	Δρmax = 0.26 e Å^−3
S = 0.99	Δρmin = −0.20 e Å^−3
2262 reflections	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
123 parameters	Extinction coefficient: 0.011 (4)
0 restraints

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
C1	0.9978 (2)	0.09560 (9)	1.1015 (2)	0.0353 (4)
H1A	1.1082	0.0787	1.0578	0.053*
H1B	0.9253	0.0551	1.1306	0.053*
H1C	1.0568	0.1244	1.2046	0.053*
C2	0.8479 (2)	0.13972 (8)	0.96498 (18)	0.0261 (4)
C3	0.6694 (2)	0.16930 (8)	1.01782 (18)	0.0270 (4)
C4	0.6481 (2)	0.16118 (9)	1.1724 (2)	0.0359 (4)
H4A	0.5283	0.1784	1.1953	0.043*
H4B	0.7526	0.1382	1.2605	0.043*
C5	0.5074 (2)	0.20555 (8)	0.8740 (2)	0.0302 (4)
H5A	0.5628	0.2507	0.8458	0.036*
H5B	0.3862	0.2163	0.9123	0.036*
C6	0.4411 (2)	0.15889 (8)	0.71321 (18)	0.0276 (4)
H6	0.326	0.181	0.6207	0.033*
C7	0.6261 (2)	0.14409 (8)	0.65093 (19)	0.0271 (4)
H7	0.5799	0.1152	0.5434	0.033*
C8	0.7577 (2)	0.09783 (8)	0.79639 (18)	0.0260 (4)
H8	0.8694	0.0739	0.7614	0.031*
C9	0.5944 (2)	0.04410 (8)	0.8111 (2)	0.0309 (4)
H9A	0.626	0.0268	0.9309	0.037*
H9B	0.5902	0.0032	0.7346	0.037*
C10	0.3852 (2)	0.08408 (8)	0.75589 (19)	0.0298 (4)
H10	0.3297	0.0864	0.8559	0.036*
C11	0.2270 (2)	0.04858 (10)	0.6052 (2)	0.0436 (5)
H11A	0.0979	0.0753	0.5755	0.065*
H11B	0.2022	0.0003	0.6373	0.065*
H11C	0.279	0.0473	0.5058	0.065*
O1	0.97149 (14)	0.19753 (6)	0.93323 (14)	0.0321 (3)
H1	0.9133	0.215	0.8359	0.048*
O2	0.73412 (15)	0.20458 (6)	0.61918 (14)	0.0320 (3)
H2	0.6493	0.2363	0.5725	0.048*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0334 (8)	0.0387 (10)	0.0319 (10)	0.0078 (7)	0.0072 (7)	0.0044 (8)
C2	0.0259 (8)	0.0261 (8)	0.0260 (9)	0.0003 (6)	0.0077 (6)	0.0031 (6)
C3	0.0307 (8)	0.0234 (8)	0.0273 (9)	0.0011 (6)	0.0095 (6)	−0.0045 (7)
C4	0.0401 (9)	0.0394 (11)	0.0300 (9)	0.0028 (8)	0.0132 (7)	−0.0032 (8)
C5	0.0288 (8)	0.0306 (9)	0.0324 (10)	0.0065 (6)	0.0111 (7)	0.0028 (7)
C6	0.0238 (7)	0.0325 (9)	0.0253 (9)	0.0015 (6)	0.0058 (6)	0.0026 (7)
C7	0.0273 (8)	0.0306 (9)	0.0243 (8)	−0.0048 (6)	0.0091 (6)	0.0003 (7)
C8	0.0275 (7)	0.0259 (9)	0.0269 (8)	0.0031 (6)	0.0118 (6)	0.0004 (7)
C9	0.0371 (9)	0.0263 (9)	0.0311 (9)	−0.0016 (7)	0.0133 (7)	−0.0019 (7)
C10	0.0298 (8)	0.0339 (9)	0.0275 (9)	−0.0062 (6)	0.0113 (6)	0.0009 (7)
C11	0.0400 (9)	0.0514 (12)	0.0377 (11)	−0.0164 (8)	0.0092 (8)	−0.0014 (9)
O1	0.0282 (6)	0.0352 (7)	0.0301 (6)	−0.0052 (5)	0.0049 (4)	0.0044 (5)
O2	0.0282 (6)	0.0348 (7)	0.0329 (7)	−0.0031 (5)	0.0093 (5)	0.0101 (5)

Geometric parameters (Å, º)

C1—C2	1.513 (2)	C6—C7	1.523 (2)
C2—O1	1.4523 (17)	C6—C10	1.534 (2)
C2—C3	1.517 (2)	C7—O2	1.4277 (17)
C2—C8	1.544 (2)	C7—C8	1.527 (2)
C3—C4	1.322 (2)	C8—C9	1.540 (2)
C3—C5	1.510 (2)	C9—C10	1.556 (2)
C5—C6	1.531 (2)	C10—C11	1.523 (2)
O1—C2—C1	104.41 (11)	C5—C6—C10	111.52 (12)
O1—C2—C3	109.41 (12)	O2—C7—C6	116.03 (13)
C1—C2—C3	114.51 (12)	O2—C7—C8	112.82 (11)
O1—C2—C8	108.87 (11)	C6—C7—C8	101.33 (12)
C1—C2—C8	111.64 (13)	C7—C8—C9	99.91 (11)
C3—C2—C8	107.85 (11)	C7—C8—C2	112.22 (12)
C4—C3—C5	121.79 (14)	C9—C8—C2	111.78 (12)
C4—C3—C2	124.03 (14)	C8—C9—C10	106.09 (12)
C5—C3—C2	114.06 (12)	C11—C10—C6	112.84 (13)
C3—C5—C6	111.02 (13)	C11—C10—C9	112.37 (13)
C7—C6—C5	109.51 (11)	C6—C10—C9	104.20 (11)
C7—C6—C10	101.22 (12)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2	0.84	1.83	2.5840 (17)	149
O2—H2···O1^i	0.84	1.87	2.7000 (15)	170

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.