The title compound, C11H18O2, is a natural product mimic containing five chiral centres.
Supporting information
CCDC reference: 189403
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (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
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).
Crystal data top
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) Å3 | Needle, colourless |
Z = 4 | 0.4 × 0.05 × 0.05 mm |
Data collection top
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 top
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.0649P)2] |
R[F2 > 2σ(F2)] = 0.046 | (Δ/σ)max = 0.01 |
wR(F2) = 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+0.001xFc2λ3/sin(2θ)]-1/4 |
123 parameters | Extinction coefficient: 0.011 (4) |
0 restraints | |
Special details top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
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···O1i | 0.84 | 1.87 | 2.7000 (15) | 170 |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |