
Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807058345/ng2371sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807058345/ng2371Isup2.hkl |
CCDC reference: 672971
The title compound was prepared in adoption of a published procedure (Corey et al., 1976) upon pinacolic coupling of cycloheptanone.
Crystals suitable for X-ray analysis were obtained after recrystallization from boiling diethylether/n-pentane.
All H atoms were located in a difference map and refined as riding on their parent atoms. One common isotropic displacement parameter for all H atoms was refined.
Data collection: CrysAlis CCD (Oxford Diffraction, 2005); cell refinement: CrysAlis RED (Oxford Diffraction, 2005); data reduction: CrysAlis RED (Oxford Diffraction, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-III (Burnett & Johnson, 1996); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C14H26O2 | F(000) = 1008 |
Mr = 226.35 | Dx = 1.134 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | θ = 3.9–26.0° |
a = 9.875 (1) Å | µ = 0.07 mm−1 |
b = 12.3662 (12) Å | T = 200 K |
c = 21.7093 (19) Å | Block, colourless |
V = 2651.1 (4) Å3 | 0.41 × 0.35 × 0.22 mm |
Z = 8 |
Nonius KappaCCD diffractometer | 2619 independent reflections |
Radiation source: fine-focus sealed tube | 2208 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.051 |
ω–scans | θmax = 26.0°, θmin = 4.3° |
Absorption correction: analytical (de Meulenaer & Tompa, 1965) | h = −11→12 |
Tmin = 0.980, Tmax = 0.987 | k = −13→15 |
12976 measured reflections | l = −26→26 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.052 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.127 | Only H-atom displacement parameters refined |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0541P)2 + 0.4645P] where P = (Fo2 + 2Fc2)/3 |
2619 reflections | (Δ/σ)max < 0.001 |
148 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
C14H26O2 | V = 2651.1 (4) Å3 |
Mr = 226.35 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 9.875 (1) Å | µ = 0.07 mm−1 |
b = 12.3662 (12) Å | T = 200 K |
c = 21.7093 (19) Å | 0.41 × 0.35 × 0.22 mm |
Nonius KappaCCD diffractometer | 2619 independent reflections |
Absorption correction: analytical (de Meulenaer & Tompa, 1965) | 2208 reflections with I > 2σ(I) |
Tmin = 0.980, Tmax = 0.987 | Rint = 0.051 |
12976 measured reflections |
R[F2 > 2σ(F2)] = 0.052 | 0 restraints |
wR(F2) = 0.127 | Only H-atom displacement parameters refined |
S = 1.16 | Δρmax = 0.21 e Å−3 |
2619 reflections | Δρmin = −0.17 e Å−3 |
148 parameters |
x | y | z | Uiso*/Ueq | ||
O1 | −0.05372 (10) | 0.31065 (9) | 0.21196 (5) | 0.0340 (3) | |
H801 | −0.1253 | 0.3298 | 0.2298 | 0.0460 (10)* | |
O2 | 0.20358 (10) | 0.34212 (10) | 0.22483 (5) | 0.0351 (3) | |
H802 | 0.1460 | 0.3084 | 0.2459 | 0.0460 (10)* | |
C1 | −0.00279 (14) | 0.39937 (11) | 0.17517 (7) | 0.0241 (3) | |
C14 | −0.01382 (16) | 0.50382 (12) | 0.21354 (7) | 0.0315 (4) | |
H141 | −0.0933 | 0.4965 | 0.2410 | 0.0460 (10)* | |
H142 | 0.0673 | 0.5083 | 0.2402 | 0.0460 (10)* | |
C13 | −0.02705 (18) | 0.61143 (13) | 0.17922 (9) | 0.0401 (4) | |
H131 | 0.0110 | 0.6697 | 0.2053 | 0.0460 (10)* | |
H132 | 0.0276 | 0.6079 | 0.1411 | 0.0460 (10)* | |
C12 | −0.17232 (19) | 0.64067 (14) | 0.16229 (10) | 0.0471 (5) | |
H121 | −0.2296 | 0.6327 | 0.1994 | 0.0460 (10)* | |
H122 | −0.1749 | 0.7177 | 0.1500 | 0.0460 (10)* | |
C11 | −0.23341 (19) | 0.57329 (15) | 0.11070 (9) | 0.0458 (5) | |
H111 | −0.1862 | 0.5917 | 0.0719 | 0.0460 (10)* | |
H112 | −0.3295 | 0.5944 | 0.1058 | 0.0460 (10)* | |
C10 | −0.22698 (16) | 0.45112 (14) | 0.11944 (8) | 0.0373 (4) | |
H101 | −0.2846 | 0.4163 | 0.0879 | 0.0460 (10)* | |
H102 | −0.2651 | 0.4329 | 0.1603 | 0.0460 (10)* | |
C9 | −0.08306 (15) | 0.40386 (13) | 0.11493 (7) | 0.0301 (4) | |
H91 | −0.0897 | 0.3296 | 0.0982 | 0.0460 (10)* | |
H92 | −0.0310 | 0.4475 | 0.0849 | 0.0460 (10)* | |
C2 | 0.14850 (14) | 0.36422 (12) | 0.16421 (7) | 0.0254 (3) | |
C3 | 0.23549 (15) | 0.45530 (13) | 0.13821 (7) | 0.0302 (4) | |
H31 | 0.2413 | 0.5133 | 0.1695 | 0.0460 (10)* | |
H32 | 0.1887 | 0.4858 | 0.1018 | 0.0460 (10)* | |
C4 | 0.37994 (16) | 0.42418 (15) | 0.11911 (8) | 0.0394 (4) | |
H41 | 0.4402 | 0.4872 | 0.1255 | 0.0460 (10)* | |
H42 | 0.4122 | 0.3652 | 0.1462 | 0.0460 (10)* | |
C5 | 0.39112 (18) | 0.38754 (17) | 0.05225 (8) | 0.0470 (5) | |
H51 | 0.3473 | 0.4426 | 0.0258 | 0.0460 (10)* | |
H52 | 0.4882 | 0.3851 | 0.0409 | 0.0460 (10)* | |
C6 | 0.32847 (18) | 0.27796 (16) | 0.03777 (8) | 0.0466 (5) | |
H61 | 0.3829 | 0.2213 | 0.0584 | 0.0460 (10)* | |
H62 | 0.3350 | 0.2655 | −0.0072 | 0.0460 (10)* | |
C7 | 0.18045 (18) | 0.26413 (15) | 0.05714 (8) | 0.0422 (4) | |
H71 | 0.1445 | 0.1972 | 0.0382 | 0.0460 (10)* | |
H72 | 0.1273 | 0.3257 | 0.0408 | 0.0460 (10)* | |
C8 | 0.15943 (17) | 0.25790 (12) | 0.12723 (8) | 0.0342 (4) | |
H81 | 0.2355 | 0.2157 | 0.1447 | 0.0460 (10)* | |
H82 | 0.0758 | 0.2159 | 0.1348 | 0.0460 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0257 (6) | 0.0342 (6) | 0.0421 (7) | 0.0008 (4) | 0.0071 (5) | 0.0105 (5) |
O2 | 0.0247 (6) | 0.0522 (7) | 0.0285 (6) | −0.0008 (5) | −0.0035 (5) | 0.0092 (5) |
C1 | 0.0226 (7) | 0.0252 (7) | 0.0245 (7) | −0.0016 (6) | 0.0009 (6) | 0.0027 (6) |
C14 | 0.0293 (8) | 0.0370 (9) | 0.0283 (8) | 0.0006 (7) | 0.0029 (6) | −0.0067 (7) |
C13 | 0.0451 (10) | 0.0283 (9) | 0.0470 (10) | −0.0026 (7) | 0.0071 (8) | −0.0079 (7) |
C12 | 0.0503 (11) | 0.0298 (9) | 0.0611 (12) | 0.0112 (8) | 0.0109 (10) | 0.0040 (8) |
C11 | 0.0373 (10) | 0.0494 (11) | 0.0507 (11) | 0.0142 (8) | −0.0017 (8) | 0.0132 (9) |
C10 | 0.0271 (9) | 0.0443 (10) | 0.0406 (9) | 0.0032 (7) | −0.0076 (7) | 0.0001 (8) |
C9 | 0.0263 (8) | 0.0342 (8) | 0.0297 (8) | 0.0016 (6) | −0.0048 (6) | −0.0039 (6) |
C2 | 0.0229 (7) | 0.0300 (8) | 0.0233 (7) | 0.0013 (6) | −0.0022 (6) | 0.0017 (6) |
C3 | 0.0247 (8) | 0.0352 (9) | 0.0308 (8) | −0.0045 (6) | 0.0011 (6) | −0.0005 (7) |
C4 | 0.0247 (8) | 0.0541 (11) | 0.0395 (10) | −0.0028 (7) | 0.0041 (7) | 0.0007 (8) |
C5 | 0.0313 (9) | 0.0723 (13) | 0.0372 (10) | 0.0043 (9) | 0.0090 (8) | 0.0032 (9) |
C6 | 0.0440 (10) | 0.0637 (12) | 0.0321 (9) | 0.0191 (9) | 0.0039 (8) | −0.0071 (8) |
C7 | 0.0415 (10) | 0.0457 (10) | 0.0395 (10) | 0.0072 (8) | −0.0042 (8) | −0.0147 (8) |
C8 | 0.0300 (8) | 0.0293 (8) | 0.0432 (10) | 0.0036 (6) | 0.0013 (7) | −0.0005 (7) |
O1—C1 | 1.4472 (17) | C9—H91 | 0.9900 |
O1—H801 | 0.8400 | C9—H92 | 0.9900 |
O2—C2 | 1.4501 (17) | C2—C3 | 1.525 (2) |
O2—H802 | 0.8400 | C2—C8 | 1.544 (2) |
C1—C9 | 1.530 (2) | C3—C4 | 1.534 (2) |
C1—C14 | 1.541 (2) | C3—H31 | 0.9900 |
C1—C2 | 1.574 (2) | C3—H32 | 0.9900 |
C14—C13 | 1.531 (2) | C4—C5 | 1.525 (2) |
C14—H141 | 0.9900 | C4—H41 | 0.9900 |
C14—H142 | 0.9900 | C4—H42 | 0.9900 |
C13—C12 | 1.524 (3) | C5—C6 | 1.522 (3) |
C13—H131 | 0.9900 | C5—H51 | 0.9900 |
C13—H132 | 0.9900 | C5—H52 | 0.9900 |
C12—C11 | 1.521 (3) | C6—C7 | 1.531 (3) |
C12—H121 | 0.9900 | C6—H61 | 0.9900 |
C12—H122 | 0.9900 | C6—H62 | 0.9900 |
C11—C10 | 1.524 (3) | C7—C8 | 1.538 (2) |
C11—H111 | 0.9900 | C7—H71 | 0.9900 |
C11—H112 | 0.9900 | C7—H72 | 0.9900 |
C10—C9 | 1.540 (2) | C8—H81 | 0.9900 |
C10—H101 | 0.9900 | C8—H82 | 0.9900 |
C10—H102 | 0.9900 | ||
C1—O1—H801 | 109.5 | H91—C9—H92 | 107.4 |
C2—O2—H802 | 109.5 | O2—C2—C3 | 105.30 (11) |
O1—C1—C9 | 108.61 (12) | O2—C2—C8 | 106.56 (12) |
O1—C1—C14 | 108.21 (12) | C3—C2—C8 | 113.40 (12) |
C9—C1—C14 | 113.26 (12) | O2—C2—C1 | 105.72 (11) |
O1—C1—C2 | 101.77 (11) | C3—C2—C1 | 112.75 (12) |
C9—C1—C2 | 111.87 (12) | C8—C2—C1 | 112.34 (12) |
C14—C1—C2 | 112.35 (12) | C2—C3—C4 | 116.00 (13) |
C13—C14—C1 | 118.14 (13) | C2—C3—H31 | 108.3 |
C13—C14—H141 | 107.8 | C4—C3—H31 | 108.3 |
C1—C14—H141 | 107.8 | C2—C3—H32 | 108.3 |
C13—C14—H142 | 107.8 | C4—C3—H32 | 108.3 |
C1—C14—H142 | 107.8 | H31—C3—H32 | 107.4 |
H141—C14—H142 | 107.1 | C5—C4—C3 | 113.52 (14) |
C12—C13—C14 | 113.82 (14) | C5—C4—H41 | 108.9 |
C12—C13—H131 | 108.8 | C3—C4—H41 | 108.9 |
C14—C13—H131 | 108.8 | C5—C4—H42 | 108.9 |
C12—C13—H132 | 108.8 | C3—C4—H42 | 108.9 |
C14—C13—H132 | 108.8 | H41—C4—H42 | 107.7 |
H131—C13—H132 | 107.7 | C6—C5—C4 | 115.57 (15) |
C11—C12—C13 | 114.89 (14) | C6—C5—H51 | 108.4 |
C11—C12—H121 | 108.5 | C4—C5—H51 | 108.4 |
C13—C12—H121 | 108.5 | C6—C5—H52 | 108.4 |
C11—C12—H122 | 108.5 | C4—C5—H52 | 108.4 |
C13—C12—H122 | 108.5 | H51—C5—H52 | 107.4 |
H121—C12—H122 | 107.5 | C5—C6—C7 | 115.52 (15) |
C12—C11—C10 | 115.78 (15) | C5—C6—H61 | 108.4 |
C12—C11—H111 | 108.3 | C7—C6—H61 | 108.4 |
C10—C11—H111 | 108.3 | C5—C6—H62 | 108.4 |
C12—C11—H112 | 108.3 | C7—C6—H62 | 108.4 |
C10—C11—H112 | 108.3 | H61—C6—H62 | 107.5 |
H111—C11—H112 | 107.4 | C6—C7—C8 | 113.98 (14) |
C11—C10—C9 | 114.00 (14) | C6—C7—H71 | 108.8 |
C11—C10—H101 | 108.8 | C8—C7—H71 | 108.8 |
C9—C10—H101 | 108.8 | C6—C7—H72 | 108.8 |
C11—C10—H102 | 108.8 | C8—C7—H72 | 108.8 |
C9—C10—H102 | 108.8 | H71—C7—H72 | 107.7 |
H101—C10—H102 | 107.6 | C7—C8—C2 | 118.76 (13) |
C1—C9—C10 | 115.95 (13) | C7—C8—H81 | 107.6 |
C1—C9—H91 | 108.3 | C2—C8—H81 | 107.6 |
C10—C9—H91 | 108.3 | C7—C8—H82 | 107.6 |
C1—C9—H92 | 108.3 | C2—C8—H82 | 107.6 |
C10—C9—H92 | 108.3 | H81—C8—H82 | 107.1 |
O1—C1—C14—C13 | −153.65 (13) | C14—C1—C2—C3 | −51.89 (16) |
C9—C1—C14—C13 | −33.17 (19) | O1—C1—C2—C8 | 62.95 (14) |
C2—C1—C14—C13 | 94.79 (16) | C9—C1—C2—C8 | −52.83 (16) |
C1—C14—C13—C12 | 86.06 (18) | C14—C1—C2—C8 | 178.48 (12) |
C14—C13—C12—C11 | −72.2 (2) | O2—C2—C3—C4 | 72.10 (16) |
C13—C12—C11—C10 | 53.4 (2) | C8—C2—C3—C4 | −44.03 (18) |
C12—C11—C10—C9 | −69.5 (2) | C1—C2—C3—C4 | −173.12 (13) |
O1—C1—C9—C10 | 75.89 (16) | C2—C3—C4—C5 | 89.91 (18) |
C14—C1—C9—C10 | −44.36 (18) | C3—C4—C5—C6 | −70.9 (2) |
C2—C1—C9—C10 | −172.58 (13) | C4—C5—C6—C7 | 53.6 (2) |
C11—C10—C9—C1 | 89.02 (18) | C5—C6—C7—C8 | −70.2 (2) |
O1—C1—C2—O2 | −52.88 (13) | C6—C7—C8—C2 | 84.19 (19) |
C9—C1—C2—O2 | −168.66 (11) | O2—C2—C8—C7 | −148.94 (14) |
C14—C1—C2—O2 | 62.64 (15) | C3—C2—C8—C7 | −33.56 (19) |
O1—C1—C2—C3 | −167.42 (12) | C1—C2—C8—C7 | 95.73 (16) |
C9—C1—C2—C3 | 76.80 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H801···O2i | 0.84 | 1.96 | 2.7889 (15) | 168 |
O2—H802···O1 | 0.84 | 2.11 | 2.5856 (15) | 116 |
Symmetry code: (i) x−1/2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H26O2 |
Mr | 226.35 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 200 |
a, b, c (Å) | 9.875 (1), 12.3662 (12), 21.7093 (19) |
V (Å3) | 2651.1 (4) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.07 |
Crystal size (mm) | 0.41 × 0.35 × 0.22 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Analytical (de Meulenaer & Tompa, 1965) |
Tmin, Tmax | 0.980, 0.987 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12976, 2619, 2208 |
Rint | 0.051 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.052, 0.127, 1.16 |
No. of reflections | 2619 |
No. of parameters | 148 |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 0.21, −0.17 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2005), CrysAlis RED (Oxford Diffraction, 2005), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-III (Burnett & Johnson, 1996).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H801···O2i | 0.84 | 1.96 | 2.7889 (15) | 168.0 |
O2—H802···O1 | 0.84 | 2.11 | 2.5856 (15) | 115.9 |
Symmetry code: (i) x−1/2, y, −z+1/2. |
Bis-1,1'-cycloheptyl-1,1'-diol was prepared as a chelating molecule bearing the sterically demanding but conformationally flexible cycloheptyl groups. In the molecule two cycloheptyl groups are connected by a single bond. The two C atoms participating in the connection are further substituted with a hydroxy group each thus comprising a vicinal diol. Both cycloheptane rings adopt a chair-like conformation (Fig. 1). Bond lengths and angles are normal.
In the crystal packing (Fig. 2), one-dimensional chains of hydrogen-bonded molecules (Fig. 3) are the dominant structural motif.