Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030527/rz6120sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030527/rz6120Isup2.hkl |
CCDC reference: 287702
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.002 Å
- R factor = 0.036
- wR factor = 0.090
- Data-to-parameter ratio = 19.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C14 .. 5.27 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C1 - C16 .. 5.65 su PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 1 C16 H30 O2
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
A solution of ethyl 12-iodo-15-oxobicyclo[9.3.1]pentadecane-1-carboxylate (1.6 g, 3.8 mmol) in tetrahydrofuran (30 ml) was treated with LiAlH4 (2.8 g, 7.62 mmol). The resulting suspension was heated under reflux for 16 h. Upon cooling to ambient temperature, water (100 ml) was carefully added, followed by HCl (concentrated) until a homogeneous solution was obtained. The solution was extracted with diethyl ether (3 × 30 ml). The combined ether layers were dried over MgSO4 and the solvent was removed to yield 0.56 g (2.2 mmol, 58%) of the title compound. 1H NMR: 3.75 (d, 1H, 3J = 10.7 Hz, H15), 3.48 (t, 2H, 3J = 11.2 Hz, CH2), 2.72 (s, OH), 2.25 (m, 3H, CH2), 2.00–1.88 (m, 8H, CH2), 1.78–1.54 (m, 4H, CH2), 1.51–1.37 (m, 4H, CH2), 1.26–1.09 (m, 2H, CH2), 0.98–0.88 (m, 4H, CH2). 13C NMR: 82.72 (C15), 72.13 (C16), 43.10 (CH2), 34.87 (CH2), 34.32 (C11), 33.18 (CH2), 29.97 (CH2), 29.85 (CH2), 27.41 (CH2), 25.79 (CH2), 24.20 (CH2), 23.56 (CH2), 22.66 (CH2), 22.05 (CH2), 21.09 (CH2), 19.84 (CH2). IR (neat): 3265 (s), 2927 (s), 2917 (s), 2852 (s), 1473 (m), 1463 (m), 1086 (m), 1050 (m), 1019 (m). LR–MS: 236 (M - H2O, 100), 218 (8), 205 (24), 109 (14), 95 (23), 81 (24), 67 (20), 55 (28), 41 (33), 29 (8).
The hydroxy H atoms were refined isotropically and the remaining H atoms were placed in calculated positions (C—H = 0.97–0.98 Å) with Uiso values constrained to be 1.2 times Ueq of the carrier atom.
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO and SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
Fig. 1. View of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are draown at the 30% probability level. |
C16H30O2 | F(000) = 568 |
Mr = 254.40 | Dx = 1.133 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 12034 reflections |
a = 13.0319 (7) Å | θ = 2.9–27.5° |
b = 8.4862 (4) Å | µ = 0.07 mm−1 |
c = 14.4047 (9) Å | T = 291 K |
β = 110.539 (3)° | Block, colourless |
V = 1491.77 (14) Å3 | 0.20 × 0.10 × 0.05 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 1996 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 27.5°, θmin = 2.9° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −16→16 |
296 frames via ω–rotation (Δω=1°) and two times 55 s per frame (two sets at different κ–angles) scans | k = −10→10 |
12034 measured reflections | l = −18→17 |
3393 independent 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)] = 0.036 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.090 | w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max < 0.001 |
3393 reflections | Δρmax = 0.19 e Å−3 |
172 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.012 (3) |
C16H30O2 | V = 1491.77 (14) Å3 |
Mr = 254.40 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.0319 (7) Å | µ = 0.07 mm−1 |
b = 8.4862 (4) Å | T = 291 K |
c = 14.4047 (9) Å | 0.20 × 0.10 × 0.05 mm |
β = 110.539 (3)° |
Nonius KappaCCD diffractometer | 1996 reflections with I > 2σ(I) |
12034 measured reflections | Rint = 0.023 |
3393 independent reflections |
R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
wR(F2) = 0.090 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.90 | Δρmax = 0.19 e Å−3 |
3393 reflections | Δρmin = −0.14 e Å−3 |
172 parameters |
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 > 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 | ||
O1 | −0.10174 (6) | 0.13418 (9) | 0.20536 (5) | 0.0409 (2) | |
H1 | −0.0544 (11) | 0.0681 (16) | 0.2393 (10) | 0.068 (4)* | |
O2 | −0.06241 (6) | 0.43668 (10) | 0.17857 (6) | 0.0527 (2) | |
H2 | −0.0663 (11) | 0.3485 (19) | 0.2109 (11) | 0.077 (5)* | |
C1 | −0.15612 (8) | 0.25184 (12) | 0.03967 (7) | 0.0374 (3) | |
C2 | −0.27356 (9) | 0.30746 (12) | 0.02644 (8) | 0.0406 (3) | |
H2A | −0.2895 | 0.3982 | −0.0173 | 0.049* | |
H2B | −0.3236 | 0.2245 | −0.0080 | 0.049* | |
C3 | −0.30136 (9) | 0.35199 (12) | 0.11760 (8) | 0.0447 (3) | |
H3A | −0.2833 | 0.4621 | 0.1328 | 0.054* | |
H3B | −0.2557 | 0.2904 | 0.1736 | 0.054* | |
C4 | −0.42131 (9) | 0.32646 (13) | 0.10606 (9) | 0.0494 (3) | |
H4A | −0.4372 | 0.3874 | 0.1564 | 0.059* | |
H4B | −0.4674 | 0.3665 | 0.0419 | 0.059* | |
C5 | −0.45137 (9) | 0.15446 (13) | 0.11461 (9) | 0.0492 (3) | |
H5A | −0.5299 | 0.1474 | 0.0992 | 0.059* | |
H5B | −0.4336 | 0.0931 | 0.0655 | 0.059* | |
C6 | −0.39400 (12) | 0.08198 (13) | 0.21577 (9) | 0.0569 (4) | |
H6A | −0.4209 | 0.1329 | 0.2630 | 0.068* | |
H6B | −0.3163 | 0.1048 | 0.2357 | 0.068* | |
C7 | −0.40828 (12) | −0.09589 (14) | 0.22229 (11) | 0.0623 (4) | |
H7A | −0.3807 | −0.1264 | 0.2916 | 0.075* | |
H7B | −0.4859 | −0.1201 | 0.1962 | 0.075* | |
C8 | −0.35087 (10) | −0.19493 (14) | 0.16704 (10) | 0.0567 (3) | |
H8A | −0.3773 | −0.1626 | 0.0981 | 0.068* | |
H8B | −0.3718 | −0.3042 | 0.1692 | 0.068* | |
C9 | −0.22551 (10) | −0.18487 (14) | 0.20681 (9) | 0.0514 (3) | |
H9A | −0.2036 | −0.0894 | 0.2458 | 0.062* | |
H9B | −0.1965 | −0.2735 | 0.2507 | 0.062* | |
C10 | −0.17471 (10) | −0.18478 (12) | 0.12647 (9) | 0.0465 (3) | |
H10A | −0.2014 | −0.2762 | 0.0845 | 0.056* | |
H10B | −0.0960 | −0.1960 | 0.1578 | 0.056* | |
C11 | −0.19829 (9) | −0.03730 (11) | 0.06066 (7) | 0.0382 (3) | |
H11 | −0.2723 | −0.0012 | 0.0528 | 0.046* | |
C12 | −0.19636 (10) | −0.07353 (14) | −0.04244 (8) | 0.0513 (3) | |
H12A | −0.1251 | −0.1163 | −0.0357 | 0.062* | |
H12B | −0.2506 | −0.1542 | −0.0726 | 0.062* | |
C13 | −0.21878 (11) | 0.06651 (15) | −0.11067 (9) | 0.0573 (3) | |
H13A | −0.2960 | 0.0928 | −0.1314 | 0.069* | |
H13B | −0.2028 | 0.0385 | −0.1695 | 0.069* | |
C14 | −0.15155 (10) | 0.21074 (14) | −0.06305 (8) | 0.0504 (3) | |
H14A | −0.1778 | 0.3004 | −0.1068 | 0.061* | |
H14B | −0.0758 | 0.1926 | −0.0564 | 0.061* | |
C15 | −0.11959 (9) | 0.10017 (11) | 0.10302 (7) | 0.0355 (3) | |
H15 | −0.0485 | 0.0695 | 0.0995 | 0.043* | |
C16 | −0.07199 (10) | 0.38332 (13) | 0.08201 (8) | 0.0488 (3) | |
H16A | −0.0008 | 0.3460 | 0.0842 | 0.059* | |
H16B | −0.0916 | 0.4724 | 0.0370 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0495 (5) | 0.0345 (4) | 0.0335 (4) | 0.0046 (4) | 0.0082 (4) | 0.0016 (3) |
O2 | 0.0583 (6) | 0.0404 (5) | 0.0504 (5) | −0.0124 (4) | 0.0080 (4) | −0.0030 (4) |
C1 | 0.0398 (6) | 0.0366 (6) | 0.0346 (6) | 0.0002 (4) | 0.0116 (5) | 0.0032 (4) |
C2 | 0.0432 (7) | 0.0351 (5) | 0.0404 (6) | 0.0051 (5) | 0.0109 (5) | 0.0063 (5) |
C3 | 0.0484 (7) | 0.0340 (6) | 0.0522 (7) | 0.0004 (5) | 0.0183 (5) | −0.0052 (5) |
C4 | 0.0477 (8) | 0.0425 (7) | 0.0590 (8) | 0.0098 (5) | 0.0202 (6) | 0.0012 (5) |
C5 | 0.0391 (7) | 0.0486 (7) | 0.0592 (8) | −0.0003 (5) | 0.0163 (6) | −0.0011 (6) |
C6 | 0.0704 (9) | 0.0474 (7) | 0.0577 (8) | 0.0056 (6) | 0.0283 (7) | −0.0002 (6) |
C7 | 0.0656 (9) | 0.0546 (8) | 0.0754 (9) | −0.0019 (6) | 0.0354 (7) | 0.0101 (7) |
C8 | 0.0592 (8) | 0.0364 (6) | 0.0777 (9) | −0.0101 (6) | 0.0279 (7) | −0.0005 (6) |
C9 | 0.0586 (8) | 0.0386 (6) | 0.0547 (7) | −0.0007 (6) | 0.0170 (6) | 0.0088 (5) |
C10 | 0.0477 (7) | 0.0315 (5) | 0.0557 (7) | 0.0031 (5) | 0.0122 (6) | −0.0016 (5) |
C11 | 0.0386 (6) | 0.0337 (5) | 0.0409 (6) | 0.0029 (5) | 0.0123 (5) | −0.0024 (5) |
C12 | 0.0550 (8) | 0.0498 (7) | 0.0472 (7) | −0.0008 (6) | 0.0156 (6) | −0.0117 (6) |
C13 | 0.0712 (9) | 0.0640 (8) | 0.0377 (7) | 0.0051 (6) | 0.0204 (6) | −0.0071 (6) |
C14 | 0.0545 (8) | 0.0579 (7) | 0.0414 (7) | 0.0049 (6) | 0.0201 (6) | 0.0072 (6) |
C15 | 0.0363 (6) | 0.0357 (6) | 0.0343 (6) | 0.0038 (4) | 0.0121 (5) | −0.0001 (4) |
C16 | 0.0499 (7) | 0.0435 (6) | 0.0517 (8) | −0.0048 (5) | 0.0162 (6) | 0.0066 (6) |
O1—C15 | 1.4387 (12) | C7—H7B | 0.9700 |
O1—H1 | 0.850 (14) | C8—C9 | 1.5323 (16) |
O2—C16 | 1.4259 (14) | C8—H8A | 0.9700 |
O2—H2 | 0.892 (16) | C8—H8B | 0.9700 |
C1—C16 | 1.5329 (15) | C9—C10 | 1.5216 (16) |
C1—C14 | 1.5415 (15) | C9—H9A | 0.9700 |
C1—C2 | 1.5482 (15) | C9—H9B | 0.9700 |
C1—C15 | 1.5529 (14) | C10—C11 | 1.5346 (14) |
C2—C3 | 1.5272 (15) | C10—H10A | 0.9700 |
C2—H2A | 0.9700 | C10—H10B | 0.9700 |
C2—H2B | 0.9700 | C11—C12 | 1.5254 (15) |
C3—C4 | 1.5282 (15) | C11—C15 | 1.5316 (14) |
C3—H3A | 0.9700 | C11—H11 | 0.9800 |
C3—H3B | 0.9700 | C12—C13 | 1.5041 (17) |
C4—C5 | 1.5274 (16) | C12—H12A | 0.9700 |
C4—H4A | 0.9700 | C12—H12B | 0.9700 |
C4—H4B | 0.9700 | C13—C14 | 1.5213 (17) |
C5—C6 | 1.5153 (17) | C13—H13A | 0.9700 |
C5—H5A | 0.9700 | C13—H13B | 0.9700 |
C5—H5B | 0.9700 | C14—H14A | 0.9700 |
C6—C7 | 1.5277 (16) | C14—H14B | 0.9700 |
C6—H6A | 0.9700 | C15—H15 | 0.9800 |
C6—H6B | 0.9700 | C16—H16A | 0.9700 |
C7—C8 | 1.5223 (18) | C16—H16B | 0.9700 |
C7—H7A | 0.9700 | ||
C15—O1—H1 | 106.3 (9) | H8A—C8—H8B | 107.5 |
C16—O2—H2 | 103.9 (9) | C10—C9—C8 | 114.02 (10) |
C16—C1—C14 | 106.47 (9) | C10—C9—H9A | 108.7 |
C16—C1—C2 | 111.42 (9) | C8—C9—H9A | 108.7 |
C14—C1—C2 | 108.68 (9) | C10—C9—H9B | 108.7 |
C16—C1—C15 | 109.90 (9) | C8—C9—H9B | 108.7 |
C14—C1—C15 | 105.63 (8) | H9A—C9—H9B | 107.6 |
C2—C1—C15 | 114.27 (8) | C9—C10—C11 | 115.09 (9) |
C3—C2—C1 | 119.48 (9) | C9—C10—H10A | 108.5 |
C3—C2—H2A | 107.4 | C11—C10—H10A | 108.5 |
C1—C2—H2A | 107.4 | C9—C10—H10B | 108.5 |
C3—C2—H2B | 107.4 | C11—C10—H10B | 108.5 |
C1—C2—H2B | 107.4 | H10A—C10—H10B | 107.5 |
H2A—C2—H2B | 107.0 | C12—C11—C15 | 107.70 (9) |
C2—C3—C4 | 114.43 (9) | C12—C11—C10 | 111.65 (9) |
C2—C3—H3A | 108.7 | C15—C11—C10 | 114.46 (8) |
C4—C3—H3A | 108.7 | C12—C11—H11 | 107.6 |
C2—C3—H3B | 108.7 | C15—C11—H11 | 107.6 |
C4—C3—H3B | 108.7 | C10—C11—H11 | 107.6 |
H3A—C3—H3B | 107.6 | C13—C12—C11 | 114.28 (9) |
C5—C4—C3 | 114.09 (9) | C13—C12—H12A | 108.7 |
C5—C4—H4A | 108.7 | C11—C12—H12A | 108.7 |
C3—C4—H4A | 108.7 | C13—C12—H12B | 108.7 |
C5—C4—H4B | 108.7 | C11—C12—H12B | 108.7 |
C3—C4—H4B | 108.7 | H12A—C12—H12B | 107.6 |
H4A—C4—H4B | 107.6 | C12—C13—C14 | 113.07 (10) |
C6—C5—C4 | 114.30 (10) | C12—C13—H13A | 109.0 |
C6—C5—H5A | 108.7 | C14—C13—H13A | 109.0 |
C4—C5—H5A | 108.7 | C12—C13—H13B | 109.0 |
C6—C5—H5B | 108.7 | C14—C13—H13B | 109.0 |
C4—C5—H5B | 108.7 | H13A—C13—H13B | 107.8 |
H5A—C5—H5B | 107.6 | C13—C14—C1 | 113.88 (9) |
C5—C6—C7 | 115.50 (11) | C13—C14—H14A | 108.8 |
C5—C6—H6A | 108.4 | C1—C14—H14A | 108.8 |
C7—C6—H6A | 108.4 | C13—C14—H14B | 108.8 |
C5—C6—H6B | 108.4 | C1—C14—H14B | 108.8 |
C7—C6—H6B | 108.4 | H14A—C14—H14B | 107.7 |
H6A—C6—H6B | 107.5 | O1—C15—C11 | 113.95 (8) |
C8—C7—C6 | 114.88 (10) | O1—C15—C1 | 109.99 (8) |
C8—C7—H7A | 108.5 | C11—C15—C1 | 111.89 (8) |
C6—C7—H7A | 108.5 | O1—C15—H15 | 106.9 |
C8—C7—H7B | 108.5 | C11—C15—H15 | 106.9 |
C6—C7—H7B | 108.5 | C1—C15—H15 | 106.9 |
H7A—C7—H7B | 107.5 | O2—C16—C1 | 115.15 (9) |
C7—C8—C9 | 115.39 (11) | O2—C16—H16A | 108.5 |
C7—C8—H8A | 108.4 | C1—C16—H16A | 108.5 |
C9—C8—H8A | 108.4 | O2—C16—H16B | 108.5 |
C7—C8—H8B | 108.4 | C1—C16—H16B | 108.5 |
C9—C8—H8B | 108.4 | H16A—C16—H16B | 107.5 |
C16—C1—C2—C3 | −64.44 (12) | C16—C1—C14—C13 | 172.11 (10) |
C14—C1—C2—C3 | 178.55 (9) | C2—C1—C14—C13 | −67.76 (12) |
C15—C1—C2—C3 | 60.88 (12) | C15—C1—C14—C13 | 55.28 (12) |
C1—C2—C3—C4 | −151.40 (9) | C12—C11—C15—O1 | −172.22 (8) |
C2—C3—C4—C5 | 76.72 (12) | C10—C11—C15—O1 | −47.43 (12) |
C3—C4—C5—C6 | 64.69 (14) | C12—C11—C15—C1 | 62.22 (11) |
C4—C5—C6—C7 | −170.85 (11) | C10—C11—C15—C1 | −173.00 (9) |
C5—C6—C7—C8 | 69.06 (16) | C16—C1—C15—O1 | 55.06 (11) |
C6—C7—C8—C9 | 64.77 (16) | C14—C1—C15—O1 | 169.54 (8) |
C7—C8—C9—C10 | −141.70 (11) | C2—C1—C15—O1 | −71.05 (11) |
C8—C9—C10—C11 | 67.67 (12) | C16—C1—C15—C11 | −177.23 (9) |
C9—C10—C11—C12 | −152.13 (10) | C14—C1—C15—C11 | −62.74 (11) |
C9—C10—C11—C15 | 85.20 (12) | C2—C1—C15—C11 | 56.66 (12) |
C15—C11—C12—C13 | −53.46 (12) | C14—C1—C16—O2 | −179.03 (9) |
C10—C11—C12—C13 | −179.92 (10) | C2—C1—C16—O2 | 62.62 (12) |
C11—C12—C13—C14 | 48.22 (15) | C15—C1—C16—O2 | −65.09 (12) |
C12—C13—C14—C1 | −49.80 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.892 (16) | 1.871 (16) | 2.6722 (11) | 148.4 (13) |
O1—H1···O2i | 0.850 (14) | 1.922 (15) | 2.7696 (11) | 174.2 (13) |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H30O2 |
Mr | 254.40 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 291 |
a, b, c (Å) | 13.0319 (7), 8.4862 (4), 14.4047 (9) |
β (°) | 110.539 (3) |
V (Å3) | 1491.77 (14) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.20 × 0.10 × 0.05 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12034, 3393, 1996 |
Rint | 0.023 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.090, 0.90 |
No. of reflections | 3393 |
No. of parameters | 172 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.19, −0.14 |
Computer programs: COLLECT (Nonius, 1998), DENZO and SCALEPACK (Otwinowski & Minor, 1997), DENZO and SCALEPACK, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1991), SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···O1 | 0.892 (16) | 1.871 (16) | 2.6722 (11) | 148.4 (13) |
O1—H1···O2i | 0.850 (14) | 1.922 (15) | 2.7696 (11) | 174.2 (13) |
Symmetry code: (i) −x, y−1/2, −z+1/2. |
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In order to study the reductive ring fragmentation (Marshall & Scanio, 1965) of keto-bridged bicyclic esters, ethyl 12-iodo-15-oxobicyclo[9.3.1]pentadecane-1-carboxylate (Fresu et al., 2004) was treated with lithium aluminium hydride. Surprisingly, the title compound, (I), isolated in 58% yield after extractive work-up, was found to result from deiodation and complete reduction of all carbonyl groups to alcohol functionalities. Reduction of the C15 keto group to alcohol gave only one epimer at the new stereogenic centre. The configuration had to be clarified by X-ray crystallography.