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The structures of enantiopure S,S-1,2-dicyclohexylethane-1,2-diol and its racemic compound (rac-S,S-1,2-dicyclohexyl­ethane-1,2-diol) have been determined at 295 and 173 K. The crystals of the enantiopure material are more than 4% denser than the crystals of the racemic compound, but the melting points indicate that the crystals of the less dense racemic compound are considerably more stable than those of the racemic conglomerate. This apparent exception to the correlation of crystal density and melting point is explained. The enantiopure crystals have four molecules in the asymmetric unit (Z' = 4). Two of the molecules have the conformation observed for the one independent molecule of the racemic compound and two have a higher energy conformation; the overall P21 structure is a perturbed version of a P212121 structure with Z' = 2. The enantiopure and racemic crystals have the same hydrogen-bonding motif, but the motif in the former appears to be significantly strained. A reason why crystals of enantiopure material might be systematically less dense than crystals of its racemic compound and to be more likely to have Z' > 1 is suggested.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768106000620/de5024sup1.cif
Contains datablocks k98005, k00009, k98064, k00013

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106000620/de5024k98005sup2.hkl
Contains datablock k98005

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106000620/de5024k00009sup3.hkl
Contains datablock k00009

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106000620/de5024k98064sup4.hkl
Contains datablock k98064

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768106000620/de5024k00013sup5.hkl
Contains datablock k00013

CCDC references: 612269; 612270; 612271; 612272

Computing details top

For all compounds, data collection: COLLECT software (Nonius, 1998); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori & Camalli, 1994) in maXus (Mackay, Gilmore, Edwards, Tremayne, Stewart & Shankland, 1998); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL PC (Sheldrick, 1990).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
(k98005) S,S-1,2-dicyclohexylethane-1,2-diol top
Crystal data top
C14H26O2Dx = 1.084 Mg m3
Mr = 226.35Melting point: 130-135 C K
Monoclinic, P1211Mo Kα radiation, λ = 0.71073 Å
a = 5.540 (1) ÅCell parameters from 49711 reflections
b = 41.653 (6) Åθ = 1.0–25.0°
c = 12.025 (2) ŵ = 0.07 mm1
β = 90.33 (1)°T = 295 K
V = 2774.8 (8) Å3Needles. Long axis is a. Prism faces are {010} and {001}., colourless
Z = 80.50 × 0.32 × 0.25 mm
F(000) = 1008
Data collection top
Nonius Kappa-CCD
diffractometer
3636 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.047
Graphite monochromatorθmax = 25.0°, θmin = 1.5°
Detector resolution: 18 pixels mm-1h = 06
ϕ and ω scans with 1.0° stepsk = 4849
9310 measured reflectionsl = 1414
4928 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.056Hydrogen site location: mixed
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.09 w = 1/[σ2(Fo2) + (0.0680)2 + 0.4P]
where P = (Fo2 + 2Fc2)/3
4928 reflections(Δ/σ)max < 0.001
610 parametersΔρmax = 0.23 e Å3
1 restraintΔρmin = 0.11 e Å3
Crystal data top
C14H26O2V = 2774.8 (8) Å3
Mr = 226.35Z = 8
Monoclinic, P1211Mo Kα radiation
a = 5.540 (1) ŵ = 0.07 mm1
b = 41.653 (6) ÅT = 295 K
c = 12.025 (2) Å0.50 × 0.32 × 0.25 mm
β = 90.33 (1)°
Data collection top
Nonius Kappa-CCD
diffractometer
3636 reflections with I > 2σ(I)
9310 measured reflectionsRint = 0.047
4928 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0561 restraint
wR(F2) = 0.144H atoms treated by a mixture of independent and constrained refinement
S = 1.09Δρmax = 0.23 e Å3
4928 reflectionsΔρmin = 0.11 e Å3
610 parameters
Special details top

Experimental. The crystal-to-detector distance was 50 mm. Each frame was measured for 100 s. The number of scan sets measured was 6; the total number of frames measured was 701.

Refinement. Friedel reflections were merged during the refinement.

The hydroxyl H atoms were located in difference maps and refined isotropically. All other H atoms were placed in calculated positions.

An instruction TWIN 1 0 0 0 − 1 0 0 0 − 1 was included. The value for the volume fraction of the second individual converged to 0.0491 (15).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O01A0.5502 (5)0.09857 (8)0.6291 (2)0.0587 (8)
H01A0.732 (14)0.1002 (19)0.629 (6)0.14 (2)*
O02A0.0464 (5)0.10222 (9)0.6135 (3)0.0545 (8)
H02A0.089 (10)0.0872 (14)0.648 (5)0.08 (2)*
C01A0.4345 (7)0.12682 (10)0.5870 (3)0.0486 (10)
H03A0.53150.14550.60900.058*
C11A0.4130 (8)0.12667 (12)0.4611 (4)0.0600 (12)
H04A0.28020.11210.44160.072*
C12A0.6425 (11)0.11375 (19)0.4036 (4)0.101 (2)
H05A0.77930.12700.42460.121*
H06A0.67410.09210.42930.121*
C13A0.6181 (14)0.1136 (2)0.2778 (5)0.124 (3)
H07A0.76900.10660.24520.148*
H08A0.49350.09840.25600.148*
C14A0.5567 (13)0.1453 (3)0.2354 (5)0.132 (3)
H09A0.53470.14410.15540.158*
H10A0.68970.15990.25030.158*
C15A0.3259 (15)0.1589 (2)0.2881 (5)0.138 (3)
H11A0.29910.18070.26260.166*
H12A0.18800.14600.26590.166*
C16A0.3525 (13)0.15845 (17)0.4148 (4)0.101 (2)
H13A0.47780.17350.43610.121*
H14A0.20250.16570.44740.121*
C02A0.1899 (7)0.12885 (10)0.6469 (3)0.0485 (10)
H15A0.10850.14820.61950.058*
C21A0.2119 (7)0.13222 (10)0.7728 (3)0.0511 (10)
H16A0.33420.11690.79890.061*
C22A0.0245 (9)0.12469 (14)0.8320 (4)0.0734 (14)
H17A0.15070.13860.80300.088*
H18A0.07020.10270.81650.088*
C23A0.0038 (11)0.12935 (15)0.9566 (4)0.0848 (17)
H19A0.15830.12470.99050.102*
H20A0.11380.11430.98630.102*
C24A0.0700 (10)0.16261 (16)0.9864 (4)0.0880 (18)
H21A0.08770.16441.06640.106*
H22A0.05370.17760.96250.106*
C25A0.3097 (11)0.17095 (17)0.9304 (5)0.0945 (18)
H23A0.35030.19320.94580.113*
H24A0.43690.15750.96100.113*
C26A0.2942 (10)0.16591 (13)0.8053 (4)0.0725 (14)
H25A0.45160.16990.77320.087*
H26A0.18230.18140.77400.087*
O01B0.1223 (6)0.04371 (8)0.7072 (3)0.0573 (8)
H01B0.007 (8)0.0409 (10)0.699 (3)0.044 (12)*
O02B0.6364 (5)0.03755 (9)0.7061 (3)0.0600 (8)
H02B0.579 (8)0.0552 (12)0.695 (4)0.052 (15)*
C01B0.2393 (6)0.01459 (11)0.6755 (3)0.0477 (10)
H03B0.13770.00350.69800.057*
C11B0.2722 (7)0.01321 (12)0.5484 (4)0.0567 (11)
H04B0.39630.02890.52820.068*
C12B0.0429 (9)0.02177 (15)0.4859 (4)0.0738 (14)
H05B0.00780.04320.50720.089*
H06B0.08400.00690.50670.089*
C13B0.0765 (12)0.02059 (16)0.3607 (5)0.0930 (18)
H07B0.07540.02570.32420.112*
H08B0.19360.03670.33900.112*
C14B0.1611 (11)0.01180 (16)0.3226 (4)0.0892 (17)
H09B0.03470.02750.33500.107*
H10B0.19360.01110.24350.107*
C15B0.3852 (12)0.02195 (19)0.3838 (5)0.102 (2)
H11B0.51880.00850.36080.122*
H12B0.42370.04390.36390.122*
C16B0.3568 (10)0.01960 (13)0.5104 (4)0.0769 (14)
H13B0.24170.03560.53460.092*
H14B0.51060.02440.54560.092*
C02B0.4756 (7)0.01299 (11)0.7407 (3)0.0515 (10)
H15B0.55180.00730.71970.062*
C21B0.4514 (7)0.01204 (11)0.8674 (3)0.0584 (11)
H16B0.31360.00180.88450.070*
C22B0.4054 (11)0.04457 (15)0.9226 (4)0.0858 (16)
H17B0.53420.05920.90280.103*
H18B0.25520.05340.89410.103*
C23B0.3912 (12)0.04234 (19)1.0477 (5)0.108 (2)
H19B0.25050.02991.06830.129*
H20B0.37350.06371.07880.129*
C24B0.6167 (12)0.0267 (2)1.0957 (5)0.107 (2)
H21B0.75410.04061.08290.128*
H22B0.59800.02431.17550.128*
C25B0.6661 (12)0.00526 (19)1.0465 (5)0.101 (2)
H23B0.54010.02011.06800.121*
H24B0.81840.01331.07520.121*
C26B0.6773 (9)0.00343 (15)0.9204 (4)0.0777 (15)
H25B0.69630.02490.89090.093*
H26B0.81840.00890.89940.093*
O01C1.0526 (5)0.30180 (8)0.9532 (2)0.0588 (8)
H01C1.197 (9)0.3004 (11)0.968 (3)0.055 (12)*
O02C0.5493 (5)0.29855 (8)0.9667 (2)0.0540 (7)
H02C0.613 (10)0.3155 (13)0.937 (4)0.081 (18)*
C01C0.9375 (6)0.27359 (10)0.9935 (3)0.0471 (10)
H03C1.03370.25500.97110.057*
C11C0.9191 (7)0.27366 (12)1.1204 (3)0.0576 (11)
H04C0.78880.28851.14020.069*
C12C1.1478 (10)0.28570 (18)1.1772 (4)0.0920 (19)
H05C1.18190.30741.15230.110*
H06C1.28260.27221.15610.110*
C13C1.1219 (13)0.2855 (2)1.3053 (5)0.115 (2)
H07C1.27270.29231.33910.138*
H08C0.99760.30061.32680.138*
C14C1.0596 (14)0.2538 (2)1.3465 (5)0.126 (3)
H09C1.03900.25471.42650.151*
H10C1.19040.23901.33090.151*
C15C0.8300 (14)0.2416 (2)1.2931 (5)0.129 (3)
H11C0.69580.25511.31470.155*
H12C0.79760.21991.31880.155*
C16C0.8534 (13)0.24160 (17)1.1649 (5)0.098 (2)
H13C0.97560.22621.14330.117*
H14C0.70120.23491.13200.117*
C02C0.6926 (6)0.27175 (10)0.9343 (3)0.0485 (10)
H15C0.61130.25240.96180.058*
C21C0.7104 (7)0.26839 (11)0.8071 (3)0.0513 (10)
H16C0.83090.28380.78090.062*
C22C0.4734 (8)0.27576 (13)0.7486 (4)0.0676 (12)
H17C0.42660.29770.76510.081*
H18C0.34910.26160.77720.081*
C23C0.4892 (11)0.27161 (16)0.6232 (4)0.0854 (16)
H19C0.33260.27580.58970.103*
H20C0.60350.28690.59320.103*
C24C0.5686 (11)0.23801 (16)0.5947 (4)0.0860 (17)
H21C0.58580.23610.51480.103*
H22C0.44660.22280.61850.103*
C25C0.8075 (11)0.23010 (16)0.6511 (4)0.0882 (17)
H23C0.84980.20800.63540.106*
H24C0.93310.24370.62070.106*
C26C0.7959 (9)0.23490 (12)0.7758 (4)0.0680 (13)
H25C0.95480.23130.80770.082*
H26C0.68690.21920.80730.082*
O01D0.6244 (5)0.35685 (7)0.8702 (2)0.0538 (8)
H01D0.476 (9)0.3591 (11)0.869 (3)0.058 (13)*
O02D1.1421 (5)0.36212 (10)0.8746 (3)0.0601 (9)
H02D1.079 (11)0.3472 (14)0.870 (5)0.08 (2)*
C01D0.7453 (7)0.38610 (11)0.9012 (4)0.0522 (10)
H03D0.64530.40430.87760.063*
C11D0.7801 (7)0.38780 (11)1.0283 (4)0.0543 (10)
H04D0.90070.37161.04870.065*
C12D0.5510 (9)0.37994 (15)1.0912 (4)0.0796 (16)
H05D0.49580.35871.06990.095*
H06D0.42620.39521.07070.095*
C13D0.5899 (11)0.38097 (15)1.2164 (4)0.0853 (17)
H07D0.43810.37671.25330.102*
H08D0.70350.36431.23780.102*
C14D0.6851 (11)0.41314 (17)1.2536 (5)0.0931 (18)
H09D0.56400.42951.24000.112*
H10D0.71850.41261.33280.112*
C15D0.9123 (11)0.42142 (17)1.1918 (5)0.0954 (18)
H11D1.03910.40661.21320.115*
H12D0.96370.44291.21250.115*
C16D0.8762 (10)0.41996 (14)1.0660 (4)0.0803 (15)
H13D0.76420.43671.04350.096*
H14D1.02920.42411.02980.096*
C02D0.9813 (6)0.38702 (11)0.8366 (3)0.0498 (10)
H15D1.05920.40740.85650.060*
C21D0.9610 (7)0.38691 (11)0.7094 (4)0.0575 (11)
H16D0.82970.40160.68900.069*
C22D0.9048 (10)0.35462 (14)0.6570 (4)0.0794 (15)
H17D0.75120.34690.68470.095*
H18D1.02800.33930.67890.095*
C23D0.8934 (11)0.35638 (18)0.5301 (4)0.100 (2)
H19D0.86480.33510.50020.120*
H20D0.75970.37000.50770.120*
C24D1.1258 (11)0.36964 (19)0.4831 (5)0.0972 (19)
H21D1.25660.35480.49860.117*
H22D1.11020.37170.40310.117*
C25D1.1847 (11)0.40159 (16)0.5324 (5)0.0911 (18)
H23D1.06350.41710.50930.109*
H24D1.33950.40880.50460.109*
C26D1.1942 (8)0.40033 (13)0.6586 (4)0.0683 (13)
H25D1.22200.42180.68720.082*
H26D1.32910.38700.68160.082*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O01A0.0379 (15)0.070 (2)0.0682 (19)0.0040 (14)0.0042 (13)0.0135 (15)
O02A0.0380 (14)0.065 (2)0.0603 (19)0.0007 (15)0.0013 (12)0.0006 (17)
C01A0.040 (2)0.058 (3)0.048 (2)0.0002 (18)0.0012 (17)0.0033 (19)
C11A0.045 (2)0.087 (4)0.048 (3)0.000 (2)0.0008 (18)0.001 (2)
C12A0.084 (4)0.161 (6)0.058 (3)0.034 (4)0.013 (3)0.003 (4)
C13A0.116 (5)0.196 (9)0.059 (4)0.038 (5)0.014 (3)0.027 (5)
C14A0.101 (5)0.233 (10)0.062 (4)0.027 (6)0.019 (3)0.028 (5)
C15A0.150 (7)0.198 (9)0.065 (4)0.053 (6)0.010 (4)0.028 (5)
C16A0.121 (5)0.118 (5)0.063 (4)0.042 (4)0.014 (3)0.018 (3)
C02A0.044 (2)0.051 (3)0.051 (2)0.0015 (19)0.0001 (17)0.0012 (19)
C21A0.046 (2)0.060 (3)0.047 (2)0.0092 (19)0.0025 (17)0.003 (2)
C22A0.062 (3)0.098 (4)0.060 (3)0.007 (3)0.015 (2)0.003 (3)
C23A0.090 (4)0.111 (5)0.054 (3)0.010 (3)0.017 (3)0.003 (3)
C24A0.099 (4)0.113 (5)0.052 (3)0.032 (4)0.003 (3)0.014 (3)
C25A0.097 (4)0.114 (5)0.072 (4)0.005 (4)0.000 (3)0.024 (3)
C26A0.083 (3)0.078 (4)0.057 (3)0.007 (3)0.013 (2)0.012 (2)
O01B0.0335 (15)0.069 (2)0.070 (2)0.0002 (15)0.0061 (14)0.0047 (15)
O02B0.0335 (14)0.070 (2)0.076 (2)0.0002 (16)0.0004 (13)0.0163 (17)
C01B0.0353 (18)0.060 (3)0.048 (2)0.0035 (19)0.0000 (16)0.005 (2)
C11B0.051 (2)0.065 (3)0.054 (3)0.006 (2)0.0014 (19)0.006 (2)
C12B0.070 (3)0.099 (4)0.052 (3)0.013 (3)0.011 (2)0.004 (3)
C13B0.099 (4)0.103 (5)0.076 (4)0.001 (4)0.030 (3)0.002 (3)
C14B0.101 (4)0.112 (5)0.055 (3)0.004 (4)0.004 (3)0.011 (3)
C15B0.101 (5)0.125 (6)0.080 (4)0.026 (4)0.007 (3)0.026 (4)
C16B0.088 (3)0.088 (4)0.055 (3)0.017 (3)0.007 (2)0.008 (3)
C02B0.041 (2)0.057 (3)0.057 (3)0.0000 (19)0.0030 (17)0.004 (2)
C21B0.048 (2)0.076 (3)0.051 (3)0.000 (2)0.0036 (18)0.006 (2)
C22B0.089 (4)0.098 (4)0.070 (4)0.020 (3)0.020 (3)0.013 (3)
C23B0.103 (4)0.160 (6)0.059 (4)0.032 (4)0.015 (3)0.018 (4)
C24B0.096 (4)0.158 (7)0.066 (4)0.004 (4)0.028 (3)0.006 (4)
C25B0.095 (4)0.136 (6)0.070 (4)0.014 (4)0.025 (3)0.023 (4)
C26B0.066 (3)0.102 (4)0.065 (3)0.021 (3)0.015 (2)0.009 (3)
O01C0.0352 (15)0.071 (2)0.070 (2)0.0017 (14)0.0044 (13)0.0165 (16)
O02C0.0362 (14)0.067 (2)0.0589 (18)0.0003 (14)0.0025 (12)0.0022 (16)
C01C0.040 (2)0.057 (3)0.045 (2)0.0029 (18)0.0036 (16)0.0018 (19)
C11C0.045 (2)0.079 (3)0.049 (3)0.001 (2)0.0010 (18)0.002 (2)
C12C0.077 (3)0.144 (6)0.055 (3)0.024 (3)0.015 (2)0.002 (3)
C13C0.111 (5)0.166 (8)0.067 (4)0.021 (5)0.019 (4)0.023 (4)
C14C0.124 (6)0.206 (9)0.049 (4)0.023 (6)0.011 (3)0.018 (4)
C15C0.131 (6)0.200 (8)0.056 (4)0.056 (6)0.008 (4)0.035 (4)
C16C0.120 (5)0.112 (5)0.061 (3)0.031 (4)0.012 (3)0.017 (3)
C02C0.0397 (19)0.052 (3)0.054 (2)0.0019 (19)0.0001 (17)0.0025 (19)
C21C0.046 (2)0.064 (3)0.044 (2)0.007 (2)0.0001 (17)0.0022 (19)
C22C0.063 (3)0.083 (4)0.056 (3)0.001 (2)0.012 (2)0.001 (2)
C23C0.095 (4)0.107 (5)0.054 (3)0.007 (3)0.024 (3)0.002 (3)
C24C0.100 (4)0.107 (5)0.051 (3)0.018 (4)0.005 (3)0.009 (3)
C25C0.093 (4)0.110 (5)0.061 (3)0.010 (3)0.003 (3)0.028 (3)
C26C0.069 (3)0.075 (3)0.059 (3)0.001 (2)0.008 (2)0.012 (2)
O01D0.0316 (14)0.069 (2)0.0613 (18)0.0027 (14)0.0054 (12)0.0095 (14)
O02D0.0348 (15)0.070 (3)0.076 (2)0.0011 (16)0.0039 (13)0.0115 (18)
C01D0.040 (2)0.054 (3)0.062 (3)0.0021 (19)0.0025 (18)0.005 (2)
C11D0.049 (2)0.054 (3)0.060 (3)0.002 (2)0.0026 (19)0.007 (2)
C12D0.067 (3)0.105 (5)0.067 (3)0.018 (3)0.018 (2)0.014 (3)
C13D0.092 (4)0.110 (5)0.054 (3)0.006 (3)0.023 (3)0.011 (3)
C14D0.100 (4)0.116 (5)0.063 (3)0.010 (4)0.004 (3)0.028 (3)
C15D0.098 (4)0.110 (5)0.079 (4)0.013 (4)0.003 (3)0.033 (3)
C16D0.087 (3)0.076 (4)0.078 (4)0.009 (3)0.009 (3)0.018 (3)
C02D0.0332 (18)0.058 (3)0.059 (3)0.0000 (18)0.0031 (17)0.005 (2)
C21D0.046 (2)0.064 (3)0.063 (3)0.002 (2)0.0089 (19)0.011 (2)
C22D0.085 (3)0.095 (4)0.058 (3)0.029 (3)0.020 (2)0.011 (3)
C23D0.100 (4)0.142 (6)0.059 (3)0.030 (4)0.018 (3)0.022 (3)
C24D0.091 (4)0.141 (6)0.059 (3)0.008 (4)0.025 (3)0.005 (4)
C25D0.091 (4)0.105 (5)0.078 (4)0.006 (3)0.028 (3)0.020 (3)
C26D0.062 (3)0.077 (3)0.066 (3)0.007 (2)0.011 (2)0.014 (2)
Geometric parameters (Å, º) top
O01A—C01A1.431 (5)C15A—H12A0.97
O02A—C02A1.421 (5)C16A—H13A0.97
C01A—C02A1.541 (5)C16A—H14A0.97
C01A—C11A1.518 (6)C21A—H16A0.98
C02A—C21A1.525 (6)C22A—H17A0.97
C11A—C12A1.548 (7)C22A—H18A0.97
C11A—C16A1.474 (8)C23A—H19A0.97
C12A—C13A1.518 (8)C23A—H20A0.97
C13A—C14A1.458 (11)C24A—H21A0.97
C14A—C15A1.538 (10)C24A—H22A0.97
C15A—C16A1.529 (8)C25A—H23A0.97
C21A—C22A1.526 (6)C25A—H24A0.97
C21A—C26A1.526 (7)C26A—H25A0.97
C22A—C23A1.515 (7)C26A—H26A0.97
C23A—C24A1.488 (9)C01B—H03B0.98
C24A—C25A1.532 (8)C02B—H15B0.98
C25A—C26A1.521 (7)C11B—H04B0.98
O01B—C01B1.429 (5)C12B—H05B0.97
O02B—C02B1.420 (5)C12B—H06B0.97
C01B—C02B1.524 (5)C13B—H07B0.97
C01B—C11B1.541 (6)C13B—H08B0.97
C02B—C21B1.530 (6)C14B—H09B0.97
C11B—C12B1.515 (6)C14B—H10B0.97
C11B—C16B1.516 (7)C15B—H11B0.97
C12B—C13B1.519 (7)C15B—H12B0.97
C13B—C14B1.500 (9)C16B—H13B0.97
C14B—C15B1.500 (8)C16B—H14B0.97
C15B—C16B1.535 (7)C21B—H16B0.98
C21B—C22B1.531 (7)C22B—H17B0.97
C21B—C26B1.543 (6)C22B—H18B0.97
C22B—C23B1.510 (7)C23B—H19B0.97
C23B—C24B1.521 (9)C23B—H20B0.97
C24B—C25B1.481 (10)C24B—H21B0.97
C25B—C26B1.520 (7)C24B—H22B0.97
O01C—C01C1.423 (5)C25B—H23B0.97
O02C—C02C1.425 (5)C25B—H24B0.97
C01C—C02C1.530 (5)C26B—H25B0.97
C01C—C11C1.530 (6)C26B—H26B0.97
C02C—C21C1.540 (6)C01C—H03C0.98
C11C—C12C1.521 (7)C02C—H15C0.98
C11C—C16C1.484 (8)C11C—H04C0.98
C12C—C13C1.549 (8)C12C—H05C0.97
C13C—C14C1.451 (11)C12C—H06C0.97
C14C—C15C1.510 (10)C13C—H07C0.97
C15C—C16C1.548 (8)C13C—H08C0.97
C21C—C22C1.517 (6)C14C—H09C0.97
C21C—C26C1.521 (7)C14C—H10C0.97
C22C—C23C1.521 (7)C15C—H11C0.97
C23C—C24C1.507 (9)C15C—H12C0.97
C24C—C25C1.520 (8)C16C—H13C0.97
C25C—C26C1.514 (7)C16C—H14C0.97
O01D—C01D1.438 (5)C21C—H16C0.98
O02D—C02D1.440 (5)C22C—H17C0.97
C01D—C02D1.525 (5)C22C—H18C0.97
C01D—C11D1.541 (6)C23C—H19C0.97
C02D—C21D1.534 (6)C23C—H20C0.97
C11D—C12D1.517 (6)C24C—H21C0.97
C11D—C16D1.510 (7)C24C—H22C0.97
C12D—C13D1.520 (7)C25C—H23C0.97
C13D—C14D1.507 (9)C25C—H24C0.97
C14D—C15D1.506 (8)C26C—H25C0.97
C15D—C16D1.525 (7)C26C—H26C0.97
C21D—C22D1.517 (7)C01D—H03D0.98
C21D—C26D1.537 (6)C02D—H15D0.98
C22D—C23D1.528 (7)C11D—H04D0.98
C23D—C24D1.513 (8)C12D—H05D0.97
C24D—C25D1.492 (9)C12D—H06D0.97
C25D—C26D1.518 (7)C13D—H07D0.97
O01A—H01A1.01 (8)C13D—H08D0.97
O02A—H02A0.79 (6)C14D—H09D0.97
O01B—H01B0.73 (4)C14D—H10D0.97
O02B—H02B0.81 (5)C15D—H11D0.97
O01C—H01C0.82 (5)C15D—H12D0.97
O02C—H02C0.87 (6)C16D—H13D0.97
O01D—H01D0.83 (5)C16D—H14D0.97
O02D—H02D0.72 (6)C21D—H16D0.98
C01A—H03A0.98C22D—H17D0.97
C02A—H15A0.98C22D—H18D0.97
C11A—H04A0.98C23D—H19D0.97
C12A—H05A0.97C23D—H20D0.97
C12A—H06A0.97C24D—H21D0.97
C13A—H07A0.97C24D—H22D0.97
C13A—H08A0.97C25D—H23D0.97
C14A—H09A0.97C25D—H24D0.97
C14A—H10A0.97C26D—H25D0.97
C15A—H11A0.97C26D—H26D0.97
O01A—C01A—C02A105.9 (3)C16B—C15B—H12B109.2
O01A—C01A—C11A112.4 (3)C11B—C16B—H13B109.0
C02A—C01A—C11A113.7 (3)C11B—C16B—H14B109.0
O02A—C02A—C01A108.5 (3)C15B—C16B—H13B109.0
O02A—C02A—C21A113.2 (3)C15B—C16B—H14B109.0
C01A—C02A—C21A113.8 (3)C02B—C21B—H16B107.3
C01A—C11A—C12A112.8 (4)C22B—C21B—H16B107.3
C01A—C11A—C16A112.9 (4)C26B—C21B—H16B107.3
C12A—C11A—C16A109.2 (5)C21B—C22B—H17B109.0
C11A—C12A—C13A112.2 (5)C21B—C22B—H18B109.0
C12A—C13A—C14A111.3 (6)C23B—C22B—H17B109.0
C13A—C14A—C15A112.4 (6)C23B—C22B—H18B109.0
C14A—C15A—C16A109.3 (6)C22B—C23B—H19B109.4
C11A—C16A—C15A114.0 (6)C22B—C23B—H20B109.4
C02A—C21A—C22A112.3 (4)C24B—C23B—H19B109.4
C02A—C21A—C26A111.2 (3)C24B—C23B—H20B109.4
C22A—C21A—C26A109.0 (4)C23B—C24B—H21B109.0
C21A—C22A—C23A112.0 (4)C23B—C24B—H22B109.0
C22A—C23A—C24A112.1 (5)C25B—C24B—H21B109.0
C23A—C24A—C25A110.0 (5)C25B—C24B—H22B109.0
C24A—C25A—C26A111.1 (5)C24B—C25B—H23B109.4
C21A—C26A—C25A113.3 (4)C24B—C25B—H24B109.4
O01B—C01B—C02B106.8 (3)C26B—C25B—H23B109.4
O01B—C01B—C11B110.7 (3)C26B—C25B—H24B109.4
C02B—C01B—C11B113.7 (3)C21B—C26B—H25B108.9
O02B—C02B—C01B110.9 (3)C21B—C26B—H26B108.9
O02B—C02B—C21B111.6 (3)C25B—C26B—H25B108.9
C01B—C02B—C21B115.7 (3)C25B—C26B—H26B108.9
C01B—C11B—C12B112.3 (3)O01C—C01C—H03C108.3
C01B—C11B—C16B111.8 (4)C02C—C01C—H03C108.3
C12B—C11B—C16B108.8 (4)C11C—C01C—H03C108.3
C11B—C12B—C13B112.1 (4)O02C—C02C—H15C107.0
C12B—C13B—C14B111.8 (5)C01C—C02C—H15C107.0
C13B—C14B—C15B111.3 (5)C21C—C02C—H15C107.0
C14B—C15B—C16B112.3 (5)C01C—C11C—H04C107.2
C11B—C16B—C15B113.0 (5)C12C—C11C—H04C107.2
C02B—C21B—C22B115.1 (4)C16C—C11C—H04C107.2
C02B—C21B—C26B110.3 (3)C11C—C12C—H05C109.4
C22B—C21B—C26B109.1 (4)C11C—C12C—H06C109.4
C21B—C22B—C23B112.8 (5)C13C—C12C—H05C109.4
C22B—C23B—C24B110.9 (5)C13C—C12C—H06C109.4
C23B—C24B—C25B112.8 (5)C12C—C13C—H07C109.3
C24B—C25B—C26B111.3 (5)C12C—C13C—H08C109.3
C21B—C26B—C25B113.3 (4)C14C—C13C—H07C109.3
O01C—C01C—C02C106.3 (3)C14C—C13C—H08C109.3
O01C—C01C—C11C111.8 (3)C13C—C14C—H09C109.4
C02C—C01C—C11C113.6 (3)C13C—C14C—H10C109.4
O02C—C02C—C01C109.1 (3)C15C—C14C—H09C109.4
O02C—C02C—C21C112.5 (3)C15C—C14C—H10C109.4
C01C—C02C—C21C113.9 (3)C14C—C15C—H11C109.6
C01C—C11C—C12C112.8 (4)C14C—C15C—H12C109.6
C01C—C11C—C16C112.0 (4)C16C—C15C—H11C109.6
C12C—C11C—C16C109.9 (5)C16C—C15C—H12C109.6
C11C—C12C—C13C111.3 (5)C11C—C16C—H13C109.1
C12C—C13C—C14C111.7 (6)C11C—C16C—H14C109.1
C13C—C14C—C15C111.3 (6)C15C—C16C—H13C109.1
C14C—C15C—C16C110.4 (6)C15C—C16C—H14C109.1
C11C—C16C—C15C112.4 (6)C02C—C21C—H16C107.9
C02C—C21C—C22C112.4 (3)C22C—C21C—H16C107.9
C02C—C21C—C26C110.6 (3)C26C—C21C—H16C107.9
C22C—C21C—C26C109.9 (4)C21C—C22C—H17C109.1
C21C—C22C—C23C112.5 (4)C21C—C22C—H18C109.1
C22C—C23C—C24C110.5 (5)C23C—C22C—H17C109.1
C23C—C24C—C25C110.8 (5)C23C—C22C—H18C109.1
C24C—C25C—C26C111.8 (5)C22C—C23C—H19C109.6
C21C—C26C—C25C112.4 (4)C22C—C23C—H20C109.6
O01D—C01D—C02D106.8 (3)C24C—C23C—H19C109.6
O01D—C01D—C11D110.6 (3)C24C—C23C—H20C109.6
C02D—C01D—C11D113.7 (3)C23C—C24C—H21C109.5
O02D—C02D—C01D110.6 (3)C23C—C24C—H22C109.5
O02D—C02D—C21D110.8 (3)C25C—C24C—H21C109.5
C01D—C02D—C21D116.7 (3)C25C—C24C—H22C109.5
C01D—C11D—C12D112.6 (4)C24C—C25C—H23C109.3
C01D—C11D—C16D112.4 (4)C24C—C25C—H24C109.3
C12D—C11D—C16D109.7 (4)C26C—C25C—H23C109.3
C11D—C12D—C13D111.9 (4)C26C—C25C—H24C109.3
C12D—C13D—C14D111.5 (5)C21C—C26C—H25C109.1
C13D—C14D—C15D110.4 (5)C21C—C26C—H26C109.1
C14D—C15D—C16D112.0 (5)C25C—C26C—H25C109.1
C11D—C16D—C15D112.2 (5)C25C—C26C—H26C109.1
C02D—C21D—C22D115.5 (4)O01D—C01D—H03D108.6
C02D—C21D—C26D109.8 (4)C02D—C01D—H03D108.6
C22D—C21D—C26D109.2 (4)C11D—C01D—H03D108.6
C21D—C22D—C23D112.3 (5)O02D—C02D—H15D106.0
C22D—C23D—C24D111.1 (5)C01D—C02D—H15D106.0
C23D—C24D—C25D111.2 (5)C21D—C02D—H15D106.0
C24D—C25D—C26D111.9 (5)C01D—C11D—H04D107.3
C25D—C26D—C21D112.6 (4)C12D—C11D—H04D107.3
C01A—O01A—H01A113 (4)C16D—C11D—H04D107.3
C02A—O02A—H02A108 (4)C11D—C12D—H05D109.2
C01B—O01B—H01B106 (3)C11D—C12D—H06D109.2
C02B—O02B—H02B117 (3)C13D—C12D—H05D109.2
C01C—O01C—H01C108 (3)C13D—C12D—H06D109.2
C02C—O02C—H02C107 (4)C12D—C13D—H07D109.3
C01D—O01D—H01D112 (3)C12D—C13D—H08D109.3
C02D—O02D—H02D107 (5)C14D—C13D—H07D109.3
O01A—C01A—H03A108.2C14D—C13D—H08D109.3
C02A—C01A—H03A108.2C13D—C14D—H09D109.6
C11A—C01A—H03A108.2C13D—C14D—H10D109.6
O02A—C02A—H15A107.0C15D—C14D—H09D109.6
C01A—C02A—H15A107.0C15D—C14D—H10D109.6
C21A—C02A—H15A107.0C14D—C15D—H11D109.2
C01A—C11A—H04A107.2C14D—C15D—H12D109.2
C12A—C11A—H04A107.2C16D—C15D—H11D109.2
C16A—C11A—H04A107.2C16D—C15D—H12D109.2
C11A—C12A—H05A109.2C11D—C16D—H13D109.2
C11A—C12A—H06A109.2C11D—C16D—H14D109.2
C13A—C12A—H05A109.2C15D—C16D—H13D109.2
C13A—C12A—H06A109.2C15D—C16D—H14D109.2
C12A—C13A—H07A109.4C02D—C21D—H16D107.3
C12A—C13A—H08A109.4C22D—C21D—H16D107.3
C14A—C13A—H07A109.4C26D—C21D—H16D107.3
C14A—C13A—H08A109.4C21D—C22D—H17D109.1
C13A—C14A—H09A109.1C21D—C22D—H18D109.1
C13A—C14A—H10A109.1C23D—C22D—H17D109.1
C15A—C14A—H09A109.1C23D—C22D—H18D109.1
C15A—C14A—H10A109.1C22D—C23D—H19D109.4
C14A—C15A—H11A109.8C22D—C23D—H20D109.4
C14A—C15A—H12A109.8C24D—C23D—H19D109.4
C16A—C15A—H11A109.8C24D—C23D—H20D109.4
C16A—C15A—H12A109.8C23D—C24D—H21D109.4
C11A—C16A—H13A108.7C23D—C24D—H22D109.4
C11A—C16A—H14A108.7C25D—C24D—H21D109.4
C15A—C16A—H13A108.7C25D—C24D—H22D109.4
C15A—C16A—H14A108.7C24D—C25D—H23D109.2
C02A—C21A—H16A108.1C24D—C25D—H24D109.2
C22A—C21A—H16A108.1C26D—C25D—H23D109.2
C26A—C21A—H16A108.1C26D—C25D—H24D109.2
C21A—C22A—H17A109.2C21D—C26D—H25D109.1
C21A—C22A—H18A109.2C21D—C26D—H26D109.1
C23A—C22A—H17A109.2C25D—C26D—H25D109.1
C23A—C22A—H18A109.2C25D—C26D—H26D109.1
C22A—C23A—H19A109.2H05A—C12A—H06A107.9
C22A—C23A—H20A109.2H07A—C13A—H08A108.0
C24A—C23A—H19A109.2H09A—C14A—H10A107.9
C24A—C23A—H20A109.2H11A—C15A—H12A108.3
C23A—C24A—H21A109.7H13A—C16A—H14A107.6
C23A—C24A—H22A109.7H17A—C22A—H18A107.9
C25A—C24A—H21A109.7H19A—C23A—H20A107.9
C25A—C24A—H22A109.7H21A—C24A—H22A108.2
C24A—C25A—H23A109.4H23A—C25A—H24A108.0
C24A—C25A—H24A109.4H25A—C26A—H26A107.7
C26A—C25A—H23A109.4H05B—C12B—H06B107.9
C26A—C25A—H24A109.4H07B—C13B—H08B107.9
C21A—C26A—H25A108.9H09B—C14B—H10B108.0
C21A—C26A—H26A108.9H11B—C15B—H12B107.9
C25A—C26A—H25A108.9H13B—C16B—H14B107.8
C25A—C26A—H26A108.9H17B—C22B—H18B107.8
O01B—C01B—H03B108.5H19B—C23B—H20B108.0
C02B—C01B—H03B108.5H21B—C24B—H22B107.8
C11B—C01B—H03B108.5H23B—C25B—H24B108.0
O02B—C02B—H15B106.0H25B—C26B—H26B107.7
C01B—C02B—H15B106.0H05C—C12C—H06C108.0
C21B—C02B—H15B106.0H07C—C13C—H08C107.9
C01B—C11B—H04B107.9H09C—C14C—H10C108.0
C12B—C11B—H04B107.9H11C—C15C—H12C108.1
C16B—C11B—H04B107.9H13C—C16C—H14C107.9
C11B—C12B—H05B109.2H17C—C22C—H18C107.8
C11B—C12B—H06B109.2H19C—C23C—H20C108.1
C13B—C12B—H05B109.2H21C—C24C—H22C108.1
C13B—C12B—H06B109.2H23C—C25C—H24C107.9
C12B—C13B—H07B109.3H25C—C26C—H26C107.9
C12B—C13B—H08B109.3H05D—C12D—H06D107.9
C14B—C13B—H07B109.3H07D—C13D—H08D108.0
C14B—C13B—H08B109.3H09D—C14D—H10D108.1
C13B—C14B—H09B109.4H11D—C15D—H12D107.9
C13B—C14B—H10B109.4H13D—C16D—H14D107.9
C15B—C14B—H09B109.4H17D—C22D—H18D107.9
C15B—C14B—H10B109.4H19D—C23D—H20D108.0
C14B—C15B—H11B109.2H21D—C24D—H22D108.0
C14B—C15B—H12B109.2H23D—C25D—H24D107.9
C16B—C15B—H11B109.2H25D—C26D—H26D107.8
O01A—C01A—C11A—C16A165.4 (4)O01C—C01C—C11C—C16C166.6 (4)
C02A—C01A—C11A—C16A74.3 (5)C02C—C01C—C11C—C16C73.1 (5)
O01A—C01A—C11A—C12A41.0 (6)O01C—C01C—C11C—C12C41.9 (5)
C02A—C01A—C11A—C12A161.3 (5)C02C—C01C—C11C—C12C162.2 (5)
C16A—C11A—C12A—C13A53.9 (8)C16C—C11C—C12C—C13C54.3 (7)
C01A—C11A—C12A—C13A179.7 (6)C01C—C11C—C12C—C13C179.9 (5)
C11A—C12A—C13A—C14A55.6 (9)C11C—C12C—C13C—C14C56.4 (8)
C12A—C13A—C14A—C15A56.0 (10)C12C—C13C—C14C—C15C56.9 (9)
C13A—C14A—C15A—C16A54.6 (10)C13C—C14C—C15C—C16C56.0 (10)
C01A—C11A—C16A—C15A179.1 (5)C12C—C11C—C16C—C15C54.7 (7)
C12A—C11A—C16A—C15A54.6 (8)C01C—C11C—C16C—C15C179.0 (5)
C14A—C15A—C16A—C11A54.9 (10)C14C—C15C—C16C—C11C55.5 (9)
O01A—C01A—C02A—O02A65.4 (4)O01C—C01C—C02C—O02C64.3 (4)
C11A—C01A—C02A—O02A58.5 (5)C11C—C01C—C02C—O02C59.0 (5)
O01A—C01A—C02A—C21A61.6 (4)O01C—C01C—C02C—C21C62.3 (4)
C11A—C01A—C02A—C21A174.5 (4)C11C—C01C—C02C—C21C174.4 (4)
O02A—C02A—C21A—C26A161.7 (4)O02C—C02C—C21C—C22C39.5 (5)
C01A—C02A—C21A—C26A73.8 (5)C01C—C02C—C21C—C22C164.2 (4)
O02A—C02A—C21A—C22A39.3 (5)O02C—C02C—C21C—C26C162.7 (3)
C01A—C02A—C21A—C22A163.8 (4)C01C—C02C—C21C—C26C72.5 (4)
C02A—C21A—C22A—C23A177.8 (4)C26C—C21C—C22C—C23C54.9 (6)
C26A—C21A—C22A—C23A54.1 (6)C02C—C21C—C22C—C23C178.5 (4)
C21A—C22A—C23A—C24A58.0 (6)C21C—C22C—C23C—C24C57.2 (6)
C22A—C23A—C24A—C25A57.0 (6)C22C—C23C—C24C—C25C56.2 (6)
C23A—C24A—C25A—C26A54.9 (7)C23C—C24C—C25C—C26C55.4 (7)
C24A—C25A—C26A—C21A54.6 (7)C24C—C25C—C26C—C21C54.2 (6)
C02A—C21A—C26A—C25A177.8 (4)C22C—C21C—C26C—C25C53.2 (5)
C22A—C21A—C26A—C25A53.4 (6)C02C—C21C—C26C—C25C177.9 (4)
O01B—C01B—C11B—C12B47.8 (5)O01D—C01D—C11D—C16D172.4 (4)
C02B—C01B—C11B—C12B168.0 (4)C02D—C01D—C11D—C16D67.5 (5)
O01B—C01B—C11B—C16B170.4 (4)O01D—C01D—C11D—C12D48.0 (5)
C02B—C01B—C11B—C16B69.3 (5)C02D—C01D—C11D—C12D168.1 (4)
C16B—C11B—C12B—C13B56.1 (6)C16D—C11D—C12D—C13D55.4 (6)
C01B—C11B—C12B—C13B179.6 (4)C01D—C11D—C12D—C13D178.7 (4)
C11B—C12B—C13B—C14B57.4 (7)C11D—C12D—C13D—C14D56.7 (6)
C12B—C13B—C14B—C15B54.2 (7)C12D—C13D—C14D—C15D55.3 (7)
C13B—C14B—C15B—C16B52.0 (8)C13D—C14D—C15D—C16D54.5 (7)
C12B—C11B—C16B—C15B54.0 (6)C12D—C11D—C16D—C15D54.4 (6)
C01B—C11B—C16B—C15B178.6 (4)C01D—C11D—C16D—C15D179.5 (4)
C14B—C15B—C16B—C11B53.2 (7)C14D—C15D—C16D—C11D55.1 (7)
O01B—C01B—C02B—O02B67.0 (4)O01D—C01D—C02D—O02D67.5 (4)
C11B—C01B—C02B—O02B55.4 (5)C11D—C01D—C02D—O02D54.7 (5)
O01B—C01B—C02B—C21B61.4 (5)O01D—C01D—C02D—C21D60.4 (5)
C11B—C01B—C02B—C21B176.1 (4)C11D—C01D—C02D—C21D177.4 (4)
O02B—C02B—C21B—C22B48.2 (5)O02D—C02D—C21D—C22D50.6 (5)
C01B—C02B—C21B—C22B79.8 (5)C01D—C02D—C21D—C22D77.2 (5)
O02B—C02B—C21B—C26B75.8 (5)O02D—C02D—C21D—C26D73.3 (5)
C01B—C02B—C21B—C26B156.2 (4)C01D—C02D—C21D—C26D158.9 (4)
C02B—C21B—C22B—C23B178.1 (4)C02D—C21D—C22D—C23D178.7 (4)
C26B—C21B—C22B—C23B53.5 (6)C26D—C21D—C22D—C23D54.4 (6)
C21B—C22B—C23B—C24B55.1 (8)C21D—C22D—C23D—C24D56.4 (7)
C22B—C23B—C24B—C25B55.1 (9)C22D—C23D—C24D—C25D55.6 (8)
C23B—C24B—C25B—C26B54.2 (8)C23D—C24D—C25D—C26D55.1 (7)
C24B—C25B—C26B—C21B53.9 (7)C24D—C25D—C26D—C21D55.0 (6)
C02B—C21B—C26B—C25B179.9 (5)C22D—C21D—C26D—C25D53.7 (6)
C22B—C21B—C26B—C25B52.7 (6)C02D—C21D—C26D—C25D178.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O01A—H01A···O02Ai1.01 (8)1.76 (8)2.760 (4)174 (6)
O01B—H01B···O02Bii0.73 (4)1.98 (5)2.704 (4)168 (4)
O01C—H01C···O02Ci0.82 (5)1.95 (5)2.759 (4)167 (4)
O01D—H01D···O02Dii0.83 (5)1.86 (5)2.682 (4)176 (5)
O02A—H02A···O01B0.79 (6)1.95 (6)2.717 (5)163 (6)
O02B—H02B···O01A0.81 (5)1.98 (5)2.746 (5)158 (4)
O02C—H02C···O01D0.87 (6)1.90 (6)2.725 (5)158 (5)
O02D—H02D···O01C0.72 (6)2.15 (6)2.731 (5)140 (6)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
(k00009) S,S-1,2-dicyclohexylethane-1,2-diol top
Crystal data top
C14H26O2Dx = 1.112 Mg m3
Mr = 226.35Melting point: 130-135 C K
Monoclinic, P1211Mo Kα radiation, λ = 0.71073 Å
a = 5.4816 (6) ÅCell parameters from 39527 reflections
b = 41.262 (6) Åθ = 1.0–25.0°
c = 11.954 (2) ŵ = 0.07 mm1
β = 90.39 (1)°T = 173 K
V = 2703.7 (7) Å3Needles. Long axis is a. Prism faces are {010} and {001}., colourless
Z = 80.44 × 0.20 × 0.16 mm
F(000) = 1008
Data collection top
Nonius Kappa-CCD
diffractometer
3750 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.034
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
Detector resolution: 18 pixels mm-1h = 66
ϕ and ω scans with 0.4° stepsk = 4848
8305 measured reflectionsl = 1414
4720 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.042Hydrogen site location: mixed
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.03 w = 1/[σ2(Fo2) + (0.042)2]
where P = (Fo2 + 2Fc2)/3
4720 reflections(Δ/σ)max < 0.001
609 parametersΔρmax = 0.12 e Å3
1 restraintΔρmin = 0.15 e Å3
Crystal data top
C14H26O2V = 2703.7 (7) Å3
Mr = 226.35Z = 8
Monoclinic, P1211Mo Kα radiation
a = 5.4816 (6) ŵ = 0.07 mm1
b = 41.262 (6) ÅT = 173 K
c = 11.954 (2) Å0.44 × 0.20 × 0.16 mm
β = 90.39 (1)°
Data collection top
Nonius Kappa-CCD
diffractometer
3750 reflections with I > 2σ(I)
8305 measured reflectionsRint = 0.034
4720 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0421 restraint
wR(F2) = 0.089H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.12 e Å3
4720 reflectionsΔρmin = 0.15 e Å3
609 parameters
Special details top

Experimental. The crystal-to-detector distance was 50 mm. Each frame was measured for 36 s. The number of scan sets measured was 4; the total number of frames measured was 1135.

Refinement. Friedel reflections were merged during the refinement.

The hydroxyl H atoms were located in difference maps and refined isotropically. All other H atoms were placed in calculated positions.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O01A0.5367 (3)0.09732 (5)0.61880 (14)0.0290 (5)
H01A0.698 (7)0.0979 (11)0.605 (3)0.098 (15)*
O02A0.0316 (3)0.10083 (5)0.60349 (14)0.0271 (5)
H02A0.097 (8)0.0804 (12)0.647 (4)0.124 (16)*
C01A0.4222 (4)0.12622 (7)0.57755 (19)0.0240 (6)
H03A0.52310.14530.60100.029*
C11A0.4026 (5)0.12607 (7)0.4502 (2)0.0266 (7)
H04A0.26770.11090.42900.032*
C12A0.6336 (5)0.11418 (9)0.3936 (2)0.0395 (8)
H05A0.77200.12820.41640.047*
H06A0.66960.09190.41900.047*
C13A0.6114 (6)0.11443 (10)0.2668 (2)0.0565 (11)
H07A0.76870.10770.23390.068*
H08A0.48570.09860.24330.068*
C14A0.5435 (6)0.14741 (11)0.2226 (2)0.0575 (10)
H09A0.51790.14620.14070.069*
H10A0.67890.16280.23730.069*
C15A0.3133 (6)0.15978 (11)0.2776 (2)0.0633 (11)
H11A0.17360.14610.25440.076*
H12A0.28050.18220.25210.076*
C16A0.3369 (6)0.15934 (8)0.4052 (2)0.0430 (9)
H13A0.46400.17500.42850.052*
H14A0.18040.16630.43830.052*
C02A0.1735 (4)0.12828 (7)0.6364 (2)0.0241 (6)
H15A0.08840.14800.60730.029*
C21A0.1938 (5)0.13185 (7)0.76393 (19)0.0244 (6)
H16A0.32130.11640.79150.029*
C22A0.0466 (5)0.12368 (8)0.8221 (2)0.0329 (7)
H17A0.17760.13780.79200.040*
H18A0.09110.10090.80560.040*
C23A0.0283 (6)0.12826 (8)0.9487 (2)0.0422 (8)
H19A0.18820.12350.98300.051*
H20A0.09280.11290.97990.051*
C24A0.0474 (5)0.16270 (8)0.9774 (2)0.0395 (8)
H21A0.06530.16491.05950.047*
H22A0.08120.17790.95220.047*
C25A0.2877 (5)0.17135 (9)0.9214 (2)0.0451 (9)
H23A0.41990.15780.95320.054*
H24A0.32750.19430.93710.054*
C26A0.2734 (5)0.16611 (8)0.7950 (2)0.0353 (7)
H25A0.15650.18180.76230.042*
H26A0.43550.17040.76220.042*
O01B0.1087 (3)0.04393 (5)0.70628 (14)0.0295 (5)
H01B0.060 (6)0.0394 (8)0.705 (2)0.049 (9)*
O02B0.6265 (3)0.03820 (5)0.71241 (15)0.0333 (5)
H02B0.541 (6)0.0576 (9)0.694 (2)0.058 (11)*
C01B0.2296 (4)0.01427 (7)0.6770 (2)0.0257 (6)
H03B0.12340.00430.69990.031*
C11B0.2677 (5)0.01235 (7)0.5494 (2)0.0271 (7)
H04B0.39440.02870.52930.033*
C12B0.0359 (5)0.02062 (8)0.4839 (2)0.0379 (8)
H05B0.09440.00510.50420.046*
H06B0.01930.04260.50490.046*
C13B0.0765 (6)0.01932 (9)0.3586 (2)0.0439 (9)
H07B0.07860.02420.31920.053*
H08B0.19720.03600.33740.053*
C14B0.1672 (5)0.01355 (8)0.3226 (2)0.0432 (8)
H09B0.20190.01320.24140.052*
H10B0.03900.03000.33600.052*
C15B0.3966 (6)0.02279 (9)0.3865 (2)0.0450 (9)
H11B0.53130.00820.36430.054*
H12B0.44360.04520.36650.054*
C16B0.3605 (5)0.02058 (8)0.5132 (2)0.0378 (8)
H13B0.24280.03740.53670.045*
H14B0.51780.02500.55140.045*
C02B0.4650 (4)0.01269 (7)0.7451 (2)0.0270 (6)
H15B0.54680.00810.72410.032*
C21B0.4359 (5)0.01198 (7)0.8730 (2)0.0290 (7)
H16B0.29760.00300.89010.035*
C22B0.3780 (6)0.04459 (8)0.9265 (2)0.0404 (8)
H17B0.50720.06030.90680.048*
H18B0.22170.05280.89560.048*
C23B0.3594 (6)0.04245 (9)1.0530 (2)0.0501 (9)
H19B0.32890.06431.08390.060*
H20B0.21950.02851.07290.060*
C24B0.5908 (6)0.02871 (9)1.1051 (2)0.0480 (9)
H21B0.72820.04381.09190.058*
H22B0.56940.02651.18690.058*
C25B0.6498 (6)0.00405 (9)1.0553 (2)0.0445 (8)
H23B0.52190.01981.07650.053*
H24B0.80730.01181.08610.053*
C26B0.6656 (5)0.00222 (8)0.9277 (2)0.0374 (8)
H25B0.69320.02430.89780.045*
H26B0.80770.01130.90720.045*
O01C1.0372 (3)0.30285 (5)0.95418 (14)0.0297 (5)
H01C1.205 (7)0.3004 (9)0.964 (3)0.076 (12)*
O02C0.5340 (3)0.29977 (5)0.96792 (14)0.0277 (5)
H02C0.605 (6)0.3190 (10)0.936 (3)0.075 (12)*
C01C0.9234 (4)0.27381 (7)0.9935 (2)0.0233 (6)
H03C1.02350.25480.96950.028*
C11C0.9055 (5)0.27356 (7)1.1210 (2)0.0278 (7)
H04C0.77240.28891.14260.033*
C12C1.1399 (5)0.28485 (9)1.1785 (2)0.0423 (9)
H05C1.27630.27071.15540.051*
H06C1.17790.30721.15400.051*
C13C1.1187 (6)0.28416 (10)1.3054 (2)0.0548 (10)
H07C1.27700.29061.33910.066*
H08C0.99490.30021.32900.066*
C14C1.0484 (6)0.25133 (11)1.3483 (2)0.0582 (11)
H09C1.02430.25241.43030.070*
H10C1.18170.23581.33350.070*
C15C0.8160 (6)0.23957 (10)1.2925 (2)0.0560 (10)
H11C0.67820.25351.31560.067*
H12C0.78090.21721.31730.067*
C16C0.8379 (6)0.24026 (8)1.1643 (2)0.0434 (8)
H13C0.96370.22451.14090.052*
H14C0.68060.23361.13040.052*
C02C0.6746 (4)0.27211 (7)0.9345 (2)0.0254 (7)
H15C0.58910.25240.96300.031*
C21C0.6907 (4)0.26888 (7)0.8071 (2)0.0251 (7)
H16C0.81700.28450.78020.030*
C22C0.4498 (5)0.27702 (8)0.7482 (2)0.0336 (7)
H17C0.31920.26300.77810.040*
H18C0.40570.29980.76450.040*
C23C0.4657 (6)0.27238 (8)0.6221 (2)0.0409 (8)
H19C0.30460.27700.58770.049*
H20C0.58470.28800.59120.049*
C24C0.5427 (5)0.23845 (8)0.5919 (2)0.0421 (8)
H21C0.56010.23670.50980.051*
H22C0.41570.22290.61580.051*
C25C0.7833 (5)0.23002 (9)0.6483 (2)0.0437 (9)
H23C0.91380.24390.61740.052*
H24C0.82480.20720.63170.052*
C26C0.7724 (5)0.23472 (8)0.7748 (2)0.0345 (7)
H25C0.93570.23050.80750.041*
H26C0.65750.21880.80680.041*
O01D0.6123 (4)0.35660 (5)0.86249 (14)0.0284 (5)
H01D0.459 (5)0.3591 (8)0.858 (2)0.041 (9)*
O02D1.1288 (3)0.36160 (5)0.86081 (15)0.0321 (5)
H02D1.048 (8)0.3438 (12)0.885 (3)0.104 (16)*
C01D0.7342 (4)0.38636 (7)0.8911 (2)0.0254 (7)
H03D0.62910.40490.86680.030*
C11D0.7732 (5)0.38854 (7)1.0183 (2)0.0295 (7)
H04D0.89810.37201.03960.035*
C12D0.5396 (5)0.38080 (8)1.0827 (2)0.0389 (8)
H05D0.48000.35901.06100.047*
H06D0.41180.39681.06280.047*
C13D0.5856 (5)0.38170 (8)1.2097 (2)0.0422 (8)
H07D0.43130.37721.24940.051*
H08D0.70440.36461.23050.051*
C14D0.6836 (5)0.41449 (9)1.2459 (2)0.0443 (8)
H09D0.72080.41411.32700.053*
H10D0.55820.43131.23220.053*
C15D0.9133 (6)0.42280 (9)1.1814 (2)0.0447 (9)
H11D1.04430.40731.20190.054*
H12D0.96850.44481.20250.054*
C16D0.8696 (5)0.42148 (8)1.0547 (2)0.0372 (8)
H13D0.75070.43851.03310.045*
H14D1.02450.42601.01560.045*
C02D0.9699 (4)0.38720 (7)0.8242 (2)0.0266 (7)
H15D1.05340.40800.84430.032*
C21D0.9452 (5)0.38698 (7)0.6965 (2)0.0292 (7)
H16D0.81470.40290.67600.035*
C22D0.8760 (5)0.35457 (8)0.6436 (2)0.0383 (8)
H17D0.71530.34760.67250.046*
H18D0.99770.33800.66600.046*
C23D0.8637 (5)0.35637 (9)0.5160 (2)0.0464 (9)
H19D0.82580.33460.48550.056*
H20D0.73060.37120.49330.056*
C24D1.1040 (5)0.36833 (9)0.4673 (2)0.0460 (9)
H21D1.23450.35240.48330.055*
H22D1.08780.37050.38510.055*
C25D1.1722 (5)0.40077 (8)0.5176 (2)0.0430 (8)
H23D1.05000.41720.49480.052*
H24D1.33280.40760.48850.052*
C26D1.1841 (5)0.39901 (8)0.6444 (2)0.0336 (7)
H25D1.22240.42080.67430.040*
H26D1.31830.38430.66670.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O01A0.0209 (11)0.0322 (13)0.0339 (12)0.0032 (9)0.0024 (8)0.0083 (9)
O02A0.0198 (10)0.0325 (13)0.0289 (11)0.0018 (9)0.0002 (7)0.0002 (9)
C01A0.0206 (14)0.0267 (18)0.0246 (15)0.0001 (13)0.0004 (11)0.0013 (12)
C11A0.0232 (15)0.0314 (19)0.0252 (15)0.0003 (13)0.0010 (11)0.0014 (13)
C12A0.0385 (17)0.056 (2)0.0245 (16)0.0142 (16)0.0026 (12)0.0008 (15)
C13A0.053 (2)0.086 (3)0.0302 (19)0.014 (2)0.0072 (15)0.0118 (19)
C14A0.057 (2)0.093 (3)0.0224 (18)0.011 (2)0.0068 (15)0.0098 (19)
C15A0.070 (2)0.092 (3)0.0279 (18)0.032 (2)0.0058 (16)0.0165 (19)
C16A0.054 (2)0.049 (2)0.0264 (17)0.0200 (17)0.0087 (14)0.0080 (15)
C02A0.0208 (14)0.0243 (18)0.0273 (15)0.0013 (13)0.0016 (11)0.0006 (12)
C21A0.0214 (14)0.0282 (18)0.0236 (15)0.0060 (13)0.0011 (11)0.0029 (12)
C22A0.0320 (16)0.038 (2)0.0292 (16)0.0030 (14)0.0058 (12)0.0005 (13)
C23A0.0467 (19)0.048 (2)0.0322 (18)0.0052 (17)0.0099 (14)0.0057 (15)
C24A0.0464 (19)0.052 (2)0.0205 (16)0.0053 (16)0.0018 (13)0.0032 (14)
C25A0.049 (2)0.054 (2)0.0323 (18)0.0031 (18)0.0013 (14)0.0112 (16)
C26A0.0347 (17)0.040 (2)0.0314 (17)0.0024 (15)0.0049 (12)0.0054 (14)
O01B0.0195 (11)0.0316 (13)0.0374 (12)0.0004 (10)0.0033 (8)0.0005 (9)
O02B0.0190 (10)0.0362 (14)0.0447 (13)0.0019 (10)0.0012 (8)0.0130 (10)
C01B0.0204 (14)0.0235 (18)0.0333 (16)0.0031 (14)0.0022 (11)0.0029 (13)
C11B0.0260 (15)0.0274 (18)0.0280 (16)0.0041 (14)0.0015 (11)0.0032 (12)
C12B0.0351 (17)0.049 (2)0.0292 (17)0.0086 (16)0.0095 (12)0.0027 (14)
C13B0.0397 (18)0.055 (3)0.0367 (19)0.0051 (17)0.0115 (14)0.0025 (16)
C14B0.046 (2)0.054 (2)0.0295 (18)0.0016 (18)0.0033 (13)0.0055 (15)
C15B0.047 (2)0.051 (2)0.0374 (19)0.0115 (18)0.0007 (14)0.0096 (16)
C16B0.0365 (17)0.040 (2)0.0365 (18)0.0066 (16)0.0027 (13)0.0002 (15)
C02B0.0224 (15)0.0238 (17)0.0347 (16)0.0014 (13)0.0007 (12)0.0042 (13)
C21B0.0239 (14)0.0334 (19)0.0297 (16)0.0001 (14)0.0019 (12)0.0051 (13)
C22B0.0415 (18)0.043 (2)0.0361 (19)0.0093 (16)0.0100 (13)0.0054 (15)
C23B0.051 (2)0.064 (3)0.0356 (19)0.0119 (19)0.0118 (15)0.0115 (16)
C24B0.046 (2)0.064 (3)0.0339 (18)0.0041 (18)0.0094 (14)0.0010 (17)
C25B0.0424 (18)0.056 (2)0.0348 (19)0.0055 (17)0.0130 (13)0.0048 (16)
C26B0.0344 (17)0.043 (2)0.0343 (18)0.0065 (16)0.0096 (13)0.0042 (14)
O01C0.0195 (11)0.0355 (13)0.0341 (12)0.0025 (10)0.0021 (8)0.0086 (9)
O02C0.0187 (10)0.0321 (13)0.0322 (12)0.0009 (10)0.0019 (8)0.0008 (9)
C01C0.0197 (14)0.0275 (18)0.0228 (15)0.0012 (13)0.0031 (11)0.0002 (12)
C11C0.0258 (15)0.036 (2)0.0221 (15)0.0011 (14)0.0014 (11)0.0002 (13)
C12C0.0400 (18)0.059 (2)0.0282 (18)0.0124 (17)0.0048 (13)0.0007 (15)
C13C0.052 (2)0.081 (3)0.031 (2)0.013 (2)0.0093 (15)0.0097 (18)
C14C0.059 (2)0.091 (3)0.0246 (18)0.014 (2)0.0083 (15)0.0058 (18)
C15C0.061 (2)0.078 (3)0.0280 (18)0.027 (2)0.0066 (15)0.0168 (17)
C16C0.057 (2)0.048 (2)0.0249 (16)0.0181 (18)0.0118 (14)0.0071 (15)
C02C0.0240 (15)0.0272 (18)0.0250 (15)0.0003 (13)0.0025 (11)0.0005 (12)
C21C0.0229 (15)0.0286 (18)0.0237 (15)0.0065 (13)0.0016 (11)0.0007 (12)
C22C0.0338 (16)0.038 (2)0.0294 (17)0.0009 (15)0.0047 (12)0.0007 (13)
C23C0.0465 (19)0.046 (2)0.0295 (17)0.0074 (17)0.0097 (13)0.0030 (15)
C24C0.0455 (19)0.053 (2)0.0279 (17)0.0108 (17)0.0038 (14)0.0040 (15)
C25C0.0446 (19)0.054 (2)0.0328 (18)0.0055 (17)0.0033 (14)0.0129 (15)
C26C0.0344 (17)0.040 (2)0.0294 (17)0.0015 (15)0.0029 (12)0.0045 (14)
O01D0.0184 (11)0.0331 (13)0.0337 (11)0.0027 (10)0.0014 (8)0.0044 (9)
O02D0.0214 (10)0.0343 (14)0.0406 (12)0.0023 (10)0.0012 (8)0.0080 (10)
C01D0.0227 (15)0.0238 (18)0.0297 (17)0.0025 (13)0.0004 (11)0.0018 (12)
C11D0.0272 (15)0.0308 (19)0.0306 (16)0.0036 (14)0.0008 (12)0.0030 (13)
C12D0.0329 (16)0.049 (2)0.0350 (18)0.0050 (16)0.0046 (13)0.0060 (15)
C13D0.0430 (18)0.053 (2)0.0306 (18)0.0034 (18)0.0098 (13)0.0076 (15)
C14D0.046 (2)0.052 (2)0.0347 (18)0.0098 (18)0.0029 (14)0.0114 (16)
C15D0.049 (2)0.044 (2)0.0406 (19)0.0086 (17)0.0007 (15)0.0136 (16)
C16D0.0387 (17)0.035 (2)0.0379 (18)0.0049 (16)0.0040 (13)0.0074 (15)
C02D0.0203 (14)0.0264 (17)0.0330 (16)0.0005 (13)0.0003 (11)0.0010 (13)
C21D0.0226 (14)0.0330 (19)0.0321 (17)0.0009 (14)0.0004 (11)0.0046 (13)
C22D0.0402 (17)0.044 (2)0.0311 (17)0.0101 (16)0.0059 (13)0.0053 (14)
C23D0.047 (2)0.060 (3)0.0324 (18)0.0101 (19)0.0064 (14)0.0063 (16)
C24D0.0457 (19)0.063 (3)0.0291 (17)0.0015 (18)0.0103 (13)0.0032 (16)
C25D0.0364 (18)0.049 (2)0.0437 (19)0.0005 (16)0.0129 (14)0.0129 (16)
C26D0.0312 (17)0.0319 (19)0.0379 (17)0.0037 (14)0.0067 (13)0.0045 (14)
Geometric parameters (Å, º) top
O01A—C01A1.433 (3)C15A—H12A0.99
O02A—C02A1.428 (3)C16A—H13A0.99
C01A—C02A1.541 (3)C16A—H14A0.99
C01A—C11A1.525 (3)C21A—H16A1.00
C02A—C21A1.534 (3)C22A—H17A0.99
C11A—C12A1.521 (3)C22A—H18A0.99
C11A—C16A1.517 (4)C23A—H19A0.99
C12A—C13A1.520 (4)C23A—H20A0.99
C13A—C14A1.505 (5)C24A—H21A0.99
C14A—C15A1.515 (4)C24A—H22A0.99
C15A—C16A1.530 (4)C25A—H23A0.99
C21A—C22A1.532 (3)C25A—H24A0.99
C21A—C26A1.525 (4)C26A—H25A0.99
C22A—C23A1.527 (3)C26A—H26A0.99
C23A—C24A1.519 (5)C01B—H03B1.00
C24A—C25A1.524 (4)C02B—H15B1.00
C25A—C26A1.528 (3)C11B—H04B1.00
O01B—C01B1.436 (3)C12B—H05B0.99
O02B—C02B1.431 (3)C12B—H06B0.99
C01B—C02B1.522 (3)C13B—H07B0.99
C01B—C11B1.543 (3)C13B—H08B0.99
C02B—C21B1.539 (3)C14B—H09B0.99
C11B—C12B1.526 (4)C14B—H10B0.99
C11B—C16B1.515 (4)C15B—H11B0.99
C12B—C13B1.516 (4)C15B—H12B0.99
C13B—C14B1.508 (5)C16B—H13B0.99
C14B—C15B1.516 (4)C16B—H14B0.99
C15B—C16B1.532 (4)C21B—H16B1.00
C21B—C22B1.524 (4)C22B—H17B0.99
C21B—C26B1.531 (4)C22B—H18B0.99
C22B—C23B1.519 (4)C23B—H19B0.99
C23B—C24B1.519 (4)C23B—H20B0.99
C24B—C25B1.513 (5)C24B—H21B0.99
C25B—C26B1.530 (4)C24B—H22B0.99
O01C—C01C1.432 (3)C25B—H23B0.99
O02C—C02C1.435 (3)C25B—H24B0.99
C01C—C02C1.532 (3)C26B—H25B0.99
C01C—C11C1.529 (3)C26B—H26B0.99
C02C—C21C1.532 (3)C01C—H03C1.00
C11C—C12C1.526 (4)C02C—H15C1.00
C11C—C16C1.515 (4)C11C—H04C1.00
C12C—C13C1.523 (4)C12C—H05C0.99
C13C—C14C1.500 (5)C12C—H06C0.99
C14C—C15C1.514 (4)C13C—H07C0.99
C15C—C16C1.539 (4)C13C—H08C0.99
C21C—C22C1.530 (4)C14C—H09C0.99
C21C—C26C1.530 (4)C14C—H10C0.99
C22C—C23C1.523 (3)C15C—H11C0.99
C23C—C24C1.507 (5)C15C—H12C0.99
C24C—C25C1.517 (4)C16C—H13C0.99
C25C—C26C1.526 (4)C16C—H14C0.99
O01D—C01D1.438 (3)C21C—H16C1.00
O02D—C02D1.436 (3)C22C—H17C0.99
C01D—C02D1.524 (3)C22C—H18C0.99
C01D—C11D1.536 (3)C23C—H19C0.99
C02D—C21D1.531 (3)C23C—H20C0.99
C11D—C12D1.532 (4)C24C—H21C0.99
C11D—C16D1.521 (4)C24C—H22C0.99
C12D—C13D1.538 (4)C25C—H23C0.99
C13D—C14D1.517 (5)C25C—H24C0.99
C14D—C15D1.520 (4)C26C—H25C0.99
C15D—C16D1.532 (4)C26C—H26C0.99
C21D—C22D1.526 (4)C01D—H03D1.00
C21D—C26D1.537 (4)C02D—H15D1.00
C22D—C23D1.529 (4)C11D—H04D1.00
C23D—C24D1.526 (4)C12D—H05D0.99
C24D—C25D1.513 (4)C12D—H06D0.99
C25D—C26D1.518 (4)C13D—H07D0.99
O01A—H01A0.90 (4)C13D—H08D0.99
O02A—H02A1.05 (5)C14D—H09D0.99
O01B—H01B0.95 (3)C14D—H10D0.99
O02B—H02B0.95 (4)C15D—H11D0.99
O01C—H01C0.93 (4)C15D—H12D0.99
O02C—H02C0.97 (4)C16D—H13D0.99
O01D—H01D0.85 (3)C16D—H14D0.99
O02D—H02D0.91 (5)C21D—H16D1.00
C01A—H03A1.00C22D—H17D0.99
C02A—H15A1.00C22D—H18D0.99
C11A—H04A1.00C23D—H19D0.99
C12A—H05A0.99C23D—H20D0.99
C12A—H06A0.99C24D—H21D0.99
C13A—H07A0.99C24D—H22D0.99
C13A—H08A0.99C25D—H23D0.99
C14A—H09A0.99C25D—H24D0.99
C14A—H10A0.99C26D—H25D0.99
C15A—H11A0.99C26D—H26D0.99
O01A—C01A—C02A106.0 (2)C16B—C15B—H12B109.3
O01A—C01A—C11A111.6 (2)C11B—C16B—H13B109.1
C02A—C01A—C11A113.6 (2)C11B—C16B—H14B109.1
O02A—C02A—C01A108.2 (2)C15B—C16B—H13B109.1
O02A—C02A—C21A112.7 (2)C15B—C16B—H14B109.1
C01A—C02A—C21A113.6 (2)C02B—C21B—H16B107.4
C01A—C11A—C12A113.1 (2)C22B—C21B—H16B107.4
C01A—C11A—C16A111.4 (2)C26B—C21B—H16B107.4
C12A—C11A—C16A109.3 (2)C21B—C22B—H17B109.1
C11A—C12A—C13A112.4 (2)C21B—C22B—H18B109.1
C12A—C13A—C14A111.9 (3)C23B—C22B—H17B109.1
C13A—C14A—C15A110.9 (3)C23B—C22B—H18B109.1
C14A—C15A—C16A111.3 (3)C22B—C23B—H19B109.3
C11A—C16A—C15A112.5 (3)C22B—C23B—H20B109.3
C02A—C21A—C22A111.9 (2)C24B—C23B—H19B109.3
C02A—C21A—C26A110.5 (2)C24B—C23B—H20B109.3
C22A—C21A—C26A109.8 (2)C23B—C24B—H21B109.5
C21A—C22A—C23A111.8 (2)C23B—C24B—H22B109.5
C22A—C23A—C24A110.8 (2)C25B—C24B—H21B109.5
C23A—C24A—C25A110.8 (3)C25B—C24B—H22B109.5
C24A—C25A—C26A111.2 (2)C24B—C25B—H23B109.4
C21A—C26A—C25A112.6 (2)C24B—C25B—H24B109.4
O01B—C01B—C02B107.3 (2)C26B—C25B—H23B109.4
O01B—C01B—C11B110.5 (2)C26B—C25B—H24B109.4
C02B—C01B—C11B114.0 (2)C21B—C26B—H25B109.0
O02B—C02B—C01B110.3 (2)C21B—C26B—H26B109.0
O02B—C02B—C21B110.7 (2)C25B—C26B—H25B109.0
C01B—C02B—C21B116.0 (2)C25B—C26B—H26B109.0
C01B—C11B—C12B112.2 (2)O01C—C01C—H03C108.7
C01B—C11B—C16B112.1 (2)C02C—C01C—H03C108.7
C12B—C11B—C16B109.5 (2)C11C—C01C—H03C108.7
C11B—C12B—C13B111.8 (2)O02C—C02C—H15C107.4
C12B—C13B—C14B111.4 (3)C01C—C02C—H15C107.4
C13B—C14B—C15B110.9 (3)C21C—C02C—H15C107.4
C14B—C15B—C16B111.8 (2)C01C—C11C—H04C107.7
C11B—C16B—C15B112.4 (2)C12C—C11C—H04C107.7
C02B—C21B—C22B115.0 (2)C16C—C11C—H04C107.7
C02B—C21B—C26B110.0 (2)C11C—C12C—H05C109.2
C22B—C21B—C26B109.4 (2)C11C—C12C—H06C109.2
C21B—C22B—C23B112.4 (3)C13C—C12C—H05C109.2
C22B—C23B—C24B111.6 (3)C13C—C12C—H06C109.2
C23B—C24B—C25B110.7 (3)C12C—C13C—H07C109.2
C24B—C25B—C26B111.2 (3)C12C—C13C—H08C109.2
C21B—C26B—C25B113.1 (2)C14C—C13C—H07C109.2
O01C—C01C—C02C106.0 (2)C14C—C13C—H08C109.2
O01C—C01C—C11C111.4 (2)C13C—C14C—H09C109.5
C02C—C01C—C11C113.3 (2)C13C—C14C—H10C109.5
O02C—C02C—C01C108.3 (2)C15C—C14C—H09C109.5
O02C—C02C—C21C112.3 (2)C15C—C14C—H10C109.5
C01C—C02C—C21C113.8 (2)C14C—C15C—H11C109.4
C01C—C11C—C12C112.8 (2)C14C—C15C—H12C109.4
C01C—C11C—C16C111.3 (2)C16C—C15C—H11C109.4
C12C—C11C—C16C109.3 (2)C16C—C15C—H12C109.4
C11C—C12C—C13C111.9 (2)C11C—C16C—H13C109.2
C12C—C13C—C14C112.3 (3)C11C—C16C—H14C109.2
C13C—C14C—C15C110.9 (3)C15C—C16C—H13C109.2
C14C—C15C—C16C111.2 (3)C15C—C16C—H14C109.2
C11C—C16C—C15C112.2 (3)C02C—C21C—H16C107.9
C02C—C21C—C22C112.5 (2)C22C—C21C—H16C107.9
C02C—C21C—C26C110.5 (2)C26C—C21C—H16C107.9
C22C—C21C—C26C109.8 (2)C21C—C22C—H17C109.2
C21C—C22C—C23C111.9 (2)C21C—C22C—H18C109.2
C22C—C23C—C24C111.8 (3)C23C—C22C—H17C109.2
C23C—C24C—C25C110.5 (3)C23C—C22C—H18C109.2
C24C—C25C—C26C111.8 (2)C22C—C23C—H19C109.2
C21C—C26C—C25C112.4 (2)C22C—C23C—H20C109.2
O01D—C01D—C02D106.8 (2)C24C—C23C—H19C109.2
O01D—C01D—C11D110.3 (2)C24C—C23C—H20C109.2
C02D—C01D—C11D113.9 (2)C23C—C24C—H21C109.5
O02D—C02D—C01D109.8 (2)C23C—C24C—H22C109.5
O02D—C02D—C21D110.4 (2)C25C—C24C—H21C109.5
C01D—C02D—C21D117.0 (2)C25C—C24C—H22C109.5
C01D—C11D—C12D112.0 (2)C24C—C25C—H23C109.3
C01D—C11D—C16D112.4 (2)C24C—C25C—H24C109.3
C12D—C11D—C16D109.4 (2)C26C—C25C—H23C109.3
C11D—C12D—C13D111.1 (2)C26C—C25C—H24C109.3
C12D—C13D—C14D111.0 (2)C21C—C26C—H25C109.1
C13D—C14D—C15D110.5 (2)C21C—C26C—H26C109.1
C14D—C15D—C16D111.6 (2)C25C—C26C—H25C109.1
C11D—C16D—C15D111.5 (2)C25C—C26C—H26C109.1
C02D—C21D—C22D116.0 (2)O01D—C01D—H03D108.6
C02D—C21D—C26D109.4 (2)C02D—C01D—H03D108.6
C22D—C21D—C26D109.0 (2)C11D—C01D—H03D108.6
C21D—C22D—C23D112.3 (2)O02D—C02D—H15D106.4
C22D—C23D—C24D111.4 (2)C01D—C02D—H15D106.4
C23D—C24D—C25D110.2 (3)C21D—C02D—H15D106.4
C24D—C25D—C26D111.3 (2)C01D—C11D—H04D107.6
C21D—C26D—C25D112.9 (2)C12D—C11D—H04D107.6
C01A—O01A—H01A110 (3)C16D—C11D—H04D107.6
C02A—O02A—H02A109 (3)C11D—C12D—H05D109.4
C01B—O01B—H01B106 (2)C11D—C12D—H06D109.4
C02B—O02B—H02B112 (2)C13D—C12D—H05D109.4
C01C—O01C—H01C108 (2)C13D—C12D—H06D109.4
C02C—O02C—H02C109 (2)C12D—C13D—H07D109.4
C01D—O01D—H01D112 (2)C12D—C13D—H08D109.4
C02D—O02D—H02D113 (3)C14D—C13D—H07D109.4
O01A—C01A—H03A108.5C14D—C13D—H08D109.4
C02A—C01A—H03A108.5C13D—C14D—H09D109.6
C11A—C01A—H03A108.5C13D—C14D—H10D109.6
O02A—C02A—H15A107.3C15D—C14D—H09D109.6
C01A—C02A—H15A107.3C15D—C14D—H10D109.6
C21A—C02A—H15A107.3C14D—C15D—H11D109.3
C01A—C11A—H04A107.6C14D—C15D—H12D109.3
C12A—C11A—H04A107.6C16D—C15D—H11D109.3
C16A—C11A—H04A107.6C16D—C15D—H12D109.3
C11A—C12A—H05A109.1C11D—C16D—H13D109.3
C11A—C12A—H06A109.1C11D—C16D—H14D109.3
C13A—C12A—H05A109.1C15D—C16D—H13D109.3
C13A—C12A—H06A109.1C15D—C16D—H14D109.3
C12A—C13A—H07A109.2C02D—C21D—H16D107.4
C12A—C13A—H08A109.2C22D—C21D—H16D107.4
C14A—C13A—H07A109.2C26D—C21D—H16D107.4
C14A—C13A—H08A109.2C21D—C22D—H17D109.1
C13A—C14A—H09A109.5C21D—C22D—H18D109.1
C13A—C14A—H10A109.5C23D—C22D—H17D109.1
C15A—C14A—H09A109.5C23D—C22D—H18D109.1
C15A—C14A—H10A109.5C22D—C23D—H19D109.4
C14A—C15A—H11A109.4C22D—C23D—H20D109.4
C14A—C15A—H12A109.4C24D—C23D—H19D109.4
C16A—C15A—H11A109.4C24D—C23D—H20D109.4
C16A—C15A—H12A109.4C23D—C24D—H21D109.6
C11A—C16A—H13A109.1C23D—C24D—H22D109.6
C11A—C16A—H14A109.1C25D—C24D—H21D109.6
C15A—C16A—H13A109.1C25D—C24D—H22D109.6
C15A—C16A—H14A109.1C24D—C25D—H23D109.4
C02A—C21A—H16A108.2C24D—C25D—H24D109.4
C22A—C21A—H16A108.2C26D—C25D—H23D109.4
C26A—C21A—H16A108.2C26D—C25D—H24D109.4
C21A—C22A—H17A109.3C21D—C26D—H25D109.0
C21A—C22A—H18A109.3C21D—C26D—H26D109.0
C23A—C22A—H17A109.3C25D—C26D—H25D109.0
C23A—C22A—H18A109.3C25D—C26D—H26D109.0
C22A—C23A—H19A109.5H05A—C12A—H06A107.9
C22A—C23A—H20A109.5H07A—C13A—H08A107.9
C24A—C23A—H19A109.5H09A—C14A—H10A108.0
C24A—C23A—H20A109.5H11A—C15A—H12A108.0
C23A—C24A—H21A109.5H13A—C16A—H14A107.8
C23A—C24A—H22A109.5H17A—C22A—H18A107.9
C25A—C24A—H21A109.5H19A—C23A—H20A108.1
C25A—C24A—H22A109.5H21A—C24A—H22A108.1
C24A—C25A—H23A109.4H23A—C25A—H24A108.0
C24A—C25A—H24A109.4H25A—C26A—H26A107.8
C26A—C25A—H23A109.4H05B—C12B—H06B107.9
C26A—C25A—H24A109.4H07B—C13B—H08B108.0
C21A—C26A—H25A109.1H09B—C14B—H10B108.1
C21A—C26A—H26A109.1H11B—C15B—H12B107.9
C25A—C26A—H25A109.1H13B—C16B—H14B107.8
C25A—C26A—H26A109.1H17B—C22B—H18B107.8
O01B—C01B—H03B108.3H19B—C23B—H20B108.0
C02B—C01B—H03B108.3H21B—C24B—H22B108.1
C11B—C01B—H03B108.3H23B—C25B—H24B108.0
O02B—C02B—H15B106.4H25B—C26B—H26B107.8
C01B—C02B—H15B106.4H05C—C12C—H06C107.9
C21B—C02B—H15B106.4H07C—C13C—H08C107.9
C01B—C11B—H04B107.6H09C—C14C—H10C108.1
C12B—C11B—H04B107.6H11C—C15C—H12C108.0
C16B—C11B—H04B107.6H13C—C16C—H14C107.9
C11B—C12B—H05B109.3H17C—C22C—H18C107.9
C11B—C12B—H06B109.3H19C—C23C—H20C107.9
C13B—C12B—H05B109.3H21C—C24C—H22C108.1
C13B—C12B—H06B109.3H23C—C25C—H24C107.9
C12B—C13B—H07B109.3H25C—C26C—H26C107.9
C12B—C13B—H08B109.3H05D—C12D—H06D108.0
C14B—C13B—H07B109.3H07D—C13D—H08D108.0
C14B—C13B—H08B109.3H09D—C14D—H10D108.1
C13B—C14B—H09B109.5H11D—C15D—H12D108.0
C13B—C14B—H10B109.5H13D—C16D—H14D108.0
C15B—C14B—H09B109.5H17D—C22D—H18D107.9
C15B—C14B—H10B109.5H19D—C23D—H20D108.0
C14B—C15B—H11B109.3H21D—C24D—H22D108.1
C14B—C15B—H12B109.3H23D—C25D—H24D108.0
C16B—C15B—H11B109.3H25D—C26D—H26D107.8
O01A—C01A—C11A—C16A166.8 (2)O01C—C01C—C11C—C16C167.4 (2)
C02A—C01A—C11A—C16A73.5 (3)C02C—C01C—C11C—C16C73.2 (3)
O01A—C01A—C11A—C12A43.2 (3)O01C—C01C—C11C—C12C44.1 (3)
C02A—C01A—C11A—C12A162.9 (3)C02C—C01C—C11C—C12C163.5 (3)
C16A—C11A—C12A—C13A54.8 (3)C16C—C11C—C12C—C13C55.2 (3)
C01A—C11A—C12A—C13A179.6 (3)C01C—C11C—C12C—C13C179.6 (3)
C11A—C12A—C13A—C14A55.8 (4)C11C—C12C—C13C—C14C55.9 (4)
C12A—C13A—C14A—C15A54.6 (4)C12C—C13C—C14C—C15C54.8 (4)
C13A—C14A—C15A—C16A54.2 (4)C13C—C14C—C15C—C16C54.3 (4)
C12A—C11A—C16A—C15A54.9 (3)C12C—C11C—C16C—C15C55.4 (3)
C01A—C11A—C16A—C15A179.4 (2)C01C—C11C—C16C—C15C179.3 (2)
C14A—C15A—C16A—C11A55.6 (4)C14C—C15C—C16C—C11C55.9 (4)
O01A—C01A—C02A—O02A63.0 (2)O01C—C01C—C02C—O02C62.3 (2)
C11A—C01A—C02A—O02A59.8 (3)C11C—C01C—C02C—O02C60.1 (3)
O01A—C01A—C02A—C21A62.9 (3)O01C—C01C—C02C—C21C63.4 (3)
C11A—C01A—C02A—C21A174.2 (2)C11C—C01C—C02C—C21C174.2 (2)
O02A—C02A—C21A—C26A162.0 (2)O02C—C02C—C21C—C26C163.0 (2)
C01A—C02A—C21A—C26A74.4 (3)C01C—C02C—C21C—C26C73.4 (3)
O02A—C02A—C21A—C22A39.3 (3)O02C—C02C—C21C—C22C39.9 (3)
C01A—C02A—C21A—C22A162.8 (3)C01C—C02C—C21C—C22C163.4 (2)
C26A—C21A—C22A—C23A55.1 (3)C26C—C21C—C22C—C23C54.1 (3)
C02A—C21A—C22A—C23A178.2 (2)C02C—C21C—C22C—C23C177.7 (2)
C21A—C22A—C23A—C24A57.2 (3)C21C—C22C—C23C—C24C56.6 (3)
C22A—C23A—C24A—C25A56.6 (3)C22C—C23C—C24C—C25C56.0 (3)
C23A—C24A—C25A—C26A55.3 (4)C23C—C24C—C25C—C26C55.0 (3)
C22A—C21A—C26A—C25A54.0 (3)C24C—C25C—C26C—C21C54.8 (3)
C02A—C21A—C26A—C25A177.9 (2)C22C—C21C—C26C—C25C53.5 (3)
C24A—C25A—C26A—C21A54.7 (4)C02C—C21C—C26C—C25C178.2 (2)
O01B—C01B—C11B—C16B171.6 (2)O01D—C01D—C11D—C16D172.1 (2)
C02B—C01B—C11B—C16B67.5 (3)C02D—C01D—C11D—C16D67.9 (3)
O01B—C01B—C11B—C12B47.9 (3)O01D—C01D—C11D—C12D48.5 (3)
C02B—C01B—C11B—C12B168.8 (3)C02D—C01D—C11D—C12D168.5 (3)
C16B—C11B—C12B—C13B56.0 (3)C16D—C11D—C12D—C13D57.1 (3)
C01B—C11B—C12B—C13B178.9 (2)C01D—C11D—C12D—C13D177.6 (2)
C11B—C12B—C13B—C14B57.5 (3)C11D—C12D—C13D—C14D57.6 (3)
C12B—C13B—C14B—C15B55.6 (3)C12D—C13D—C14D—C15D56.0 (3)
C13B—C14B—C15B—C16B53.7 (4)C13D—C14D—C15D—C16D55.4 (4)
C12B—C11B—C16B—C15B54.2 (3)C12D—C11D—C16D—C15D56.4 (3)
C01B—C11B—C16B—C15B179.5 (2)C01D—C11D—C16D—C15D178.5 (2)
C14B—C15B—C16B—C11B54.2 (3)C14D—C15D—C16D—C11D56.4 (3)
O01B—C01B—C02B—O02B65.2 (2)O01D—C01D—C02D—O02D65.5 (3)
C11B—C01B—C02B—O02B57.5 (3)C11D—C01D—C02D—O02D56.5 (3)
O01B—C01B—C02B—C21B61.7 (3)O01D—C01D—C02D—C21D61.2 (3)
C11B—C01B—C02B—C21B175.7 (2)C11D—C01D—C02D—C21D176.8 (2)
O02B—C02B—C21B—C22B49.2 (3)O02D—C02D—C21D—C22D51.6 (3)
C01B—C02B—C21B—C22B77.4 (3)C01D—C02D—C21D—C22D74.8 (3)
O02B—C02B—C21B—C26B74.8 (3)O02D—C02D—C21D—C26D72.1 (3)
C01B—C02B—C21B—C26B158.6 (3)C01D—C02D—C21D—C26D161.5 (3)
C26B—C21B—C22B—C23B53.9 (3)C02D—C21D—C22D—C23D178.1 (2)
C02B—C21B—C22B—C23B178.2 (2)C26D—C21D—C22D—C23D54.2 (3)
C21B—C22B—C23B—C24B56.5 (4)C21D—C22D—C23D—C24D56.4 (3)
C22B—C23B—C24B—C25B56.1 (4)C22D—C23D—C24D—C25D56.0 (4)
C23B—C24B—C25B—C26B54.9 (4)C23D—C24D—C25D—C26D55.9 (3)
C24B—C25B—C26B—C21B54.9 (3)C24D—C25D—C26D—C21D56.4 (3)
C22B—C21B—C26B—C25B53.3 (3)C22D—C21D—C26D—C25D54.4 (3)
C02B—C21B—C26B—C25B179.5 (2)C02D—C21D—C26D—C25D177.8 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O01A—H01A···O02Ai0.90 (4)1.83 (4)2.724 (2)170 (4)
O01B—H01B···O02Bii0.95 (3)1.72 (3)2.656 (3)169 (3)
O01C—H01C···O02Ci0.93 (4)1.80 (4)2.730 (2)172 (3)
O01D—H01D···O02Dii0.85 (3)1.81 (3)2.658 (3)174 (3)
O02A—H02A···O01B1.05 (5)1.66 (5)2.682 (3)161 (4)
O02B—H02B···O01A0.95 (4)1.87 (4)2.727 (3)149 (3)
O02C—H02C···O01D0.97 (4)1.78 (4)2.698 (3)157 (3)
O02D—H02D···O01C0.91 (5)1.88 (5)2.717 (3)152 (4)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
(k98064) rac-1,2-dicyclohexylethane-1,2-diol top
Crystal data top
C14H26O2Dx = 1.037 Mg m3
Mr = 226.35Melting point: 147 C K
Monoclinic, C12/c1Mo Kα radiation, λ = 0.71073 Å
a = 23.153 (5) ÅCell parameters from 13065 reflections
b = 11.852 (3) Åθ = 1.7–25.0°
c = 10.926 (2) ŵ = 0.07 mm1
β = 104.64 (2)°T = 295 K
V = 2900.9 (11) Å3Laths. Largest faces are {100}; long direction is c., colourless
Z = 80.31 × 0.22 × 0.13 mm
F(000) = 1008
Data collection top
Nonius Kappa-CCD
diffractometer
1942 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.023
Graphite monochromatorθmax = 25.0°, θmin = 2.6°
Detector resolution: 18 pixels mm-1h = 2627
ϕ and ω scans with 1.0° stepsk = 1414
4869 measured reflectionsl = 120
2529 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.068Hydrogen site location: mixed
wR(F2) = 0.208H atoms treated by a mixture of independent and constrained refinement
S = 1.13 w = 1/[σ2(Fo2) + (0.11P)2 + 0.59P]
where P = (Fo2 + 2Fc2)/3
2529 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.14 e Å3
64 restraintsΔρmin = 0.12 e Å3
Crystal data top
C14H26O2V = 2900.9 (11) Å3
Mr = 226.35Z = 8
Monoclinic, C12/c1Mo Kα radiation
a = 23.153 (5) ŵ = 0.07 mm1
b = 11.852 (3) ÅT = 295 K
c = 10.926 (2) Å0.31 × 0.22 × 0.13 mm
β = 104.64 (2)°
Data collection top
Nonius Kappa-CCD
diffractometer
1942 reflections with I > 2σ(I)
4869 measured reflectionsRint = 0.023
2529 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06864 restraints
wR(F2) = 0.208H atoms treated by a mixture of independent and constrained refinement
S = 1.13Δρmax = 0.14 e Å3
2529 reflectionsΔρmin = 0.12 e Å3
211 parameters
Special details top

Experimental. The crystal-to-detector distance was 25 mm. Each frame was measured for 240 s. The number of scan sets measured was 2; the total number of frames measured was 222.

Refinement. The hydroxyl H atoms were located in difference maps. U values were 1.2 times the equivalent U values of the attached O atoms. The O—H distances were restrained (DFIX 0.84 (1)). All other H atoms were placed in calculated positions.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O010.00320 (8)0.86884 (15)0.13101 (14)0.0858 (6)
H91A0.009 (2)0.855 (4)0.196 (3)0.103*0.50
H91B0.002 (2)0.935 (2)0.104 (5)0.103*0.50
O020.00741 (7)0.90575 (16)0.12551 (14)0.0815 (6)
H92A0.012 (2)0.903 (4)0.199 (2)0.098*0.50
H92B0.023 (2)0.969 (2)0.121 (5)0.098*0.50
C010.00935 (8)0.78050 (16)0.04696 (15)0.0576 (5)
H010.03300.72030.09730.069*
C020.04468 (8)0.82661 (17)0.04236 (15)0.0580 (5)
H020.05280.76370.09380.070*
C110.05141 (8)0.73155 (17)0.01917 (16)0.0610 (5)
H110.07490.79220.06900.073*
C120.08477 (12)0.6922 (3)0.0772 (2)0.0940 (8)
H12A0.06080.63650.13250.113*
H12B0.09030.75590.12880.113*
C130.14533 (13)0.6413 (3)0.0146 (3)0.1127 (10)
H13A0.16390.61420.07940.135*
H13B0.17090.69900.03380.135*
C140.13966 (14)0.5461 (3)0.0707 (3)0.1199 (11)
H14A0.17900.51780.11230.144*
H14B0.11730.48510.02120.144*
C150.10837 (14)0.5841 (3)0.1686 (3)0.1252 (12)
H15A0.13320.63880.22410.150*
H15B0.10290.51990.21960.150*
C160.04750 (11)0.6372 (2)0.1086 (3)0.0918 (8)
H16A0.02090.57950.06310.110*
H16B0.03050.66600.17500.110*
C21A0.1061 (6)0.8740 (19)0.032 (2)0.067 (4)0.50
H21A0.09820.92490.09620.081*0.50
C22A0.1356 (6)0.9452 (12)0.0521 (12)0.097 (4)0.50
H22A0.10911.00650.08890.116*0.50
H22B0.14210.89890.12060.116*0.50
C23A0.1951 (7)0.9936 (13)0.0229 (16)0.120 (4)0.50
H23A0.21441.03280.03400.144*0.50
H23B0.18821.04760.08430.144*0.50
C24A0.2353 (6)0.9011 (18)0.0900 (19)0.124 (5)0.50
H24A0.27210.93410.14020.148*0.50
H24B0.24540.85170.02780.148*0.50
C25A0.2067 (9)0.8326 (18)0.175 (2)0.133 (5)0.50
H25A0.20030.88010.24280.160*0.50
H25B0.23340.77190.21310.160*0.50
C26A0.1468 (7)0.7828 (14)0.1012 (17)0.089 (3)0.50
H26A0.15380.72750.04110.107*0.50
H26B0.12780.74480.15930.107*0.50
C21B0.1027 (7)0.886 (2)0.017 (2)0.065 (3)0.50
H21B0.09340.95250.06080.078*0.50
C22B0.1337 (6)0.9262 (15)0.0836 (14)0.114 (5)0.50
H22C0.10700.97530.14320.137*0.50
H22D0.14310.86180.12990.137*0.50
C23B0.1913 (8)0.9902 (18)0.0215 (16)0.142 (7)0.50
H23C0.21031.01490.08660.171*0.50
H23D0.18141.05690.02050.171*0.50
C24B0.2340 (7)0.920 (2)0.072 (2)0.141 (7)0.50
H24C0.26860.96470.11250.169*0.50
H24D0.24750.85730.02900.169*0.50
C25B0.2046 (9)0.8745 (18)0.1719 (17)0.135 (7)0.50
H25C0.19700.93650.22360.162*0.50
H25D0.23160.82230.22640.162*0.50
C26B0.1460 (8)0.8143 (13)0.1121 (15)0.100 (5)0.50
H26C0.15450.74610.07090.120*0.50
H26D0.12720.79230.17840.120*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O010.1187 (13)0.0891 (12)0.0598 (9)0.0275 (10)0.0414 (9)0.0249 (8)
O020.0808 (10)0.0954 (12)0.0679 (9)0.0045 (8)0.0178 (8)0.0356 (9)
C010.0734 (12)0.0591 (11)0.0403 (8)0.0075 (9)0.0145 (8)0.0007 (7)
C020.0689 (12)0.0632 (11)0.0423 (8)0.0045 (9)0.0147 (8)0.0011 (8)
C110.0674 (12)0.0631 (12)0.0518 (9)0.0065 (9)0.0136 (8)0.0046 (8)
C120.0974 (17)0.110 (2)0.0837 (15)0.0367 (15)0.0390 (13)0.0038 (14)
C130.0945 (19)0.118 (2)0.134 (2)0.0335 (18)0.0450 (18)0.002 (2)
C140.097 (2)0.110 (2)0.146 (3)0.0494 (18)0.0180 (18)0.005 (2)
C150.112 (2)0.140 (3)0.116 (2)0.052 (2)0.0151 (18)0.053 (2)
C160.0883 (16)0.0982 (18)0.0899 (15)0.0265 (14)0.0242 (13)0.0314 (14)
C21A0.063 (5)0.080 (9)0.059 (6)0.016 (4)0.015 (4)0.004 (5)
C22A0.078 (5)0.106 (5)0.097 (8)0.004 (4)0.005 (4)0.033 (5)
C23A0.078 (5)0.127 (7)0.145 (12)0.036 (5)0.007 (6)0.038 (6)
C24A0.067 (6)0.154 (10)0.133 (9)0.024 (6)0.006 (6)0.014 (8)
C25A0.079 (6)0.150 (12)0.146 (9)0.022 (6)0.015 (5)0.045 (7)
C26A0.062 (4)0.087 (7)0.108 (6)0.001 (4)0.001 (4)0.014 (4)
C21B0.076 (6)0.065 (5)0.055 (5)0.004 (4)0.018 (4)0.012 (4)
C22B0.087 (5)0.183 (10)0.081 (5)0.055 (5)0.036 (4)0.022 (5)
C23B0.089 (7)0.205 (12)0.125 (10)0.051 (6)0.011 (6)0.069 (8)
C24B0.076 (7)0.171 (13)0.178 (12)0.026 (8)0.035 (6)0.062 (10)
C25B0.089 (7)0.184 (17)0.109 (7)0.049 (9)0.020 (5)0.067 (9)
C26B0.088 (7)0.109 (10)0.096 (6)0.026 (6)0.010 (5)0.038 (7)
Geometric parameters (Å, º) top
O01—C011.423 (2)C12—H12B0.97
O02—C021.433 (2)C13—H13A0.97
C01—C021.524 (2)C13—H13B0.97
C01—C111.525 (3)C14—H14A0.97
C11—C121.527 (3)C14—H14B0.97
C11—C161.503 (3)C15—H15A0.97
C12—C131.521 (3)C15—H15B0.97
C13—C141.490 (4)C16—H16A0.97
C14—C151.505 (4)C16—H16B0.97
C15—C161.531 (3)C21A—H21A0.98
C02—C21A1.553 (18)C21B—H21B0.98
C21A—C22A1.526 (10)C22A—H22A0.97
C21A—C26A1.507 (12)C22A—H22B0.97
C22A—C23A1.526 (10)C22B—H22C0.97
C23A—C24A1.503 (12)C22B—H22D0.97
C24A—C25A1.509 (11)C23A—H23A0.97
C25A—C26A1.535 (11)C23A—H23B0.97
C02—C21B1.51 (2)C23B—H23C0.97
C21B—C22B1.530 (12)C23B—H23D0.97
C21B—C26B1.510 (10)C24A—H24A0.97
C22B—C23B1.536 (11)C24A—H24B0.97
C23B—C24B1.486 (11)C24B—H24C0.97
C24B—C25B1.522 (12)C24B—H24D0.97
C25B—C26B1.527 (10)C25A—H25A0.97
O01—H91A0.84 (2)C25A—H25B0.97
O01—H91B0.84 (2)C25B—H25C0.97
O02—H92A0.83 (2)C25B—H25D0.97
O02—H92B0.84 (2)C26A—H26A0.97
C01—H010.98C26A—H26B0.97
C02—H020.98C26B—H26C0.97
C11—H110.98C26B—H26D0.97
C12—H12A0.97
O01—C01—C02107.86 (15)C11—C16—H16B109.1
O01—C01—C11110.78 (16)C15—C16—H16A109.1
C02—C01—C11114.41 (13)C15—C16—H16B109.1
O02—C02—C01107.81 (15)C02—C21A—H21A106.5
O02—C02—C21A114.8 (7)C22A—C21A—H21A106.5
O02—C02—C21B107.2 (7)C26A—C21A—H21A106.5
C01—C02—C21A111.4 (7)C02—C21B—H21B107.6
C01—C02—C21B117.3 (7)C22B—C21B—H21B107.6
C01—C11—C12110.88 (15)C26B—C21B—H21B107.6
C01—C11—C16113.03 (17)C21A—C22A—H22A109.3
C12—C11—C16110.20 (19)C21A—C22A—H22B109.3
C11—C12—C13112.4 (2)C23A—C22A—H22A109.3
C12—C13—C14111.4 (2)C23A—C22A—H22B109.3
C13—C14—C15110.6 (3)C21B—C22B—H22C109.5
C14—C15—C16112.0 (2)C21B—C22B—H22D109.5
C11—C16—C15112.6 (2)C23B—C22B—H22C109.5
C02—C21A—C22A112.2 (12)C23B—C22B—H22D109.5
C02—C21A—C26A112.2 (14)C22A—C23A—H23A109.5
C22A—C21A—C26A112.4 (11)C22A—C23A—H23B109.5
C21A—C22A—C23A111.5 (10)C24A—C23A—H23A109.5
C22A—C23A—C24A110.6 (9)C24A—C23A—H23B109.5
C23A—C24A—C25A112.3 (11)C22B—C23B—H23C109.1
C24A—C25A—C26A111.2 (11)C22B—C23B—H23D109.1
C21A—C26A—C25A110.9 (12)C24B—C23B—H23C109.1
C02—C21B—C22B111.6 (15)C24B—C23B—H23D109.1
C02—C21B—C26B113.5 (14)C23A—C24A—H24A109.1
C22B—C21B—C26B108.8 (11)C23A—C24A—H24B109.1
C21B—C22B—C23B110.5 (12)C25A—C24A—H24A109.1
C22B—C23B—C24B112.3 (12)C25A—C24A—H24B109.1
C23B—C24B—C25B110.6 (10)C23B—C24B—H24C109.5
C24B—C25B—C26B111.6 (12)C23B—C24B—H24D109.5
C21B—C26B—C25B113.4 (11)C25B—C24B—H24C109.5
C01—O01—H91A121 (3)C25B—C24B—H24D109.5
C01—O01—H91B119 (4)C24A—C25A—H25A109.4
H91A—O01—H91B115 (5)C24A—C25A—H25B109.4
C02—O02—H92A113 (4)C26A—C25A—H25A109.4
C02—O02—H92B112 (4)C26A—C25A—H25B109.4
H92A—O02—H92B86 (5)C24B—C25B—H25C109.3
O01—C01—H01107.8C24B—C25B—H25D109.3
C02—C01—H01107.8C26B—C25B—H25C109.3
C11—C01—H01107.9C26B—C25B—H25D109.3
O02—C02—H02107.8C21A—C26A—H26A109.5
C01—C02—H02107.8C21A—C26A—H26B109.5
C21A—C02—H02106.9C25A—C26A—H26A109.5
C21B—C02—H02108.6C25A—C26A—H26B109.5
C01—C11—H11107.5C21B—C26B—H26C108.9
C12—C11—H11107.5C21B—C26B—H26D108.9
C16—C11—H11107.5C25B—C26B—H26C108.9
C11—C12—H12A109.1C25B—C26B—H26D108.9
C11—C12—H12B109.1H12A—C12—H12B107.9
C13—C12—H12A109.1H13A—C13—H13B108.0
C13—C12—H12B109.1H14A—C14—H14B108.1
C12—C13—H13A109.4H15A—C15—H15B107.9
C12—C13—H13B109.4H16A—C16—H16B107.8
C14—C13—H13A109.4H22A—C22A—H22B108.0
C14—C13—H13B109.4H22C—C22B—H22D108.1
C13—C14—H14A109.5H23A—C23A—H23B108.1
C13—C14—H14B109.5H23C—C23B—H23D107.9
C15—C14—H14A109.5H24A—C24A—H24B107.9
C15—C14—H14B109.5H24C—C24B—H24D108.1
C14—C15—H15A109.2H25A—C25A—H25B108.0
C14—C15—H15B109.2H25C—C25B—H25D108.0
C16—C15—H15A109.2H26A—C26A—H26B108.0
C16—C15—H15B109.2H26C—C26B—H26D107.7
C11—C16—H16A109.1
O01—C01—C02—O0270.08 (18)C01—C02—C21A—C22A166.3 (11)
C11—C01—C02—O0253.7 (2)C26A—C21A—C22A—C23A54 (2)
O01—C01—C02—C21B50.9 (10)C02—C21A—C22A—C23A178.5 (14)
C11—C01—C02—C21B174.7 (10)C21A—C22A—C23A—C24A54.3 (18)
O01—C01—C02—C21A56.7 (9)C22A—C23A—C24A—C25A56.2 (19)
C11—C01—C02—C21A179.5 (9)C23A—C24A—C25A—C26A56 (2)
O01—C01—C11—C16179.62 (18)C22A—C21A—C26A—C25A53 (2)
C02—C01—C11—C1658.2 (2)C02—C21A—C26A—C25A179.0 (16)
O01—C01—C11—C1255.3 (2)C24A—C25A—C26A—C21A54 (2)
C02—C01—C11—C12177.49 (19)O02—C02—C21B—C26B177.2 (13)
C16—C11—C12—C1353.3 (3)C01—C02—C21B—C26B55.9 (19)
C01—C11—C12—C13179.2 (2)C21A—C02—C21B—C26B12 (12)
C11—C12—C13—C1456.2 (4)O02—C02—C21B—C22B59.4 (17)
C12—C13—C14—C1556.4 (4)C01—C02—C21B—C22B179.3 (10)
C13—C14—C15—C1655.3 (4)C21A—C02—C21B—C22B136 (15)
C01—C11—C16—C15176.7 (2)C26B—C21B—C22B—C23B56 (2)
C12—C11—C16—C1552.0 (3)C02—C21B—C22B—C23B177.7 (16)
C14—C15—C16—C1154.1 (4)C21B—C22B—C23B—C24B59 (2)
O02—C02—C21A—C26A171.0 (11)C22B—C23B—C24B—C25B56 (2)
C21B—C02—C21A—C26A155 (15)C23B—C24B—C25B—C26B53 (2)
C01—C02—C21A—C26A66.1 (16)C02—C21B—C26B—C25B179.8 (17)
O02—C02—C21A—C22A43.4 (18)C22B—C21B—C26B—C25B55 (2)
C21B—C02—C21A—C22A28 (13)C24B—C25B—C26B—C21B54 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O01—H91A···O01i0.84 (2)1.87 (2)2.641 (3)152 (5)
O01—H91B···O02ii0.84 (2)1.91 (3)2.682 (3)153 (6)
O02—H92A···O02iii0.83 (2)1.86 (2)2.654 (3)160 (5)
O02—H92B···O01ii0.84 (2)2.01 (4)2.682 (3)138 (5)
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+2, z; (iii) x, y, z1/2.
(k00013) rac-1,2-dicyclohexylethane-1,2-diol top
Crystal data top
C14H26O2Dx = 1.063 Mg m3
Mr = 226.35Melting point: 147 C K
Monoclinic, C12/c1Mo Kα radiation, λ = 0.71073 Å
a = 23.161 (5) ÅCell parameters from 9027 reflections
b = 11.584 (3) Åθ = 1.0–25.0°
c = 10.973 (2) ŵ = 0.07 mm1
β = 106.10 (2)°T = 173 K
V = 2828.6 (11) Å3Laths. Largest faces are {100}; long direction is c., colourless
Z = 80.56 × 0.55 × 0.10 mm
F(000) = 1008
Data collection top
Nonius Kappa-CCD
diffractometer
1911 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.021
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
Detector resolution: 18 pixels mm-1h = 2727
ϕ and ω scans with 2.0° stepsk = 1313
4693 measured reflectionsl = 1313
2489 independent reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.047Hydrogen site location: mixed
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.06 w = 1/[σ2(Fo2) + (0.048P)2 + 1.16P]
where P = (Fo2 + 2Fc2)/3
2489 reflections(Δ/σ)max < 0.001
211 parametersΔρmax = 0.15 e Å3
64 restraintsΔρmin = 0.19 e Å3
Crystal data top
C14H26O2V = 2828.6 (11) Å3
Mr = 226.35Z = 8
Monoclinic, C12/c1Mo Kα radiation
a = 23.161 (5) ŵ = 0.07 mm1
b = 11.584 (3) ÅT = 173 K
c = 10.973 (2) Å0.56 × 0.55 × 0.10 mm
β = 106.10 (2)°
Data collection top
Nonius Kappa-CCD
diffractometer
1911 reflections with I > 2σ(I)
4693 measured reflectionsRint = 0.021
2489 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04764 restraints
wR(F2) = 0.118H atoms treated by a mixture of independent and constrained refinement
S = 1.06Δρmax = 0.15 e Å3
2489 reflectionsΔρmin = 0.19 e Å3
211 parameters
Special details top

Experimental. The crystal-to-detector distance was 36 mm. Each frame was measured for 60 s. The number of scan sets measured was 5; the total number of frames measured was 226.

Refinement. The hydroxyl H atoms were located in difference maps. U values were 1.2 times the equivalent U values of the attached O atoms. The O—H distances were restrained (DFIX 0.86 (1)). All other H atoms were placed in calculated positions.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O010.00852 (5)0.86681 (10)0.13541 (10)0.0490 (3)
H91A0.0037 (15)0.850 (3)0.200 (2)0.059*0.50
H91B0.0080 (15)0.9299 (18)0.106 (3)0.059*0.50
O020.00541 (5)0.90468 (11)0.12722 (11)0.0531 (4)
H92A0.0080 (17)0.902 (3)0.2021 (15)0.064*0.50
H92B0.0029 (16)0.9757 (11)0.128 (4)0.064*0.50
C010.01143 (6)0.77787 (12)0.04737 (11)0.0314 (3)
H010.03510.71760.09770.038*
C020.04474 (6)0.82578 (12)0.04343 (12)0.0319 (4)
H020.05280.76290.09490.038*
C110.05120 (6)0.73106 (12)0.01791 (12)0.0316 (4)
H110.07560.79640.06550.038*
C120.08270 (7)0.68793 (15)0.07867 (14)0.0465 (4)
H12A0.05780.62710.13160.056*
H12B0.08630.75250.13520.056*
C130.14482 (7)0.63967 (15)0.01596 (16)0.0533 (5)
H13A0.16260.60980.08190.064*
H13B0.17100.70220.03020.064*
C140.14204 (8)0.54396 (16)0.07531 (19)0.0616 (5)
H14A0.18320.51690.11810.074*
H14B0.11910.47810.02810.074*
C150.11206 (7)0.58586 (17)0.17386 (17)0.0620 (5)
H15A0.13770.64530.22760.074*
H15B0.10830.52050.22930.074*
C160.04989 (7)0.63666 (14)0.11326 (15)0.0458 (4)
H16A0.02260.57430.07010.055*
H16B0.03360.66880.18060.055*
C21A0.1078 (5)0.8816 (11)0.0323 (13)0.030 (2)0.50
H21A0.10180.93360.10050.036*0.50
C22A0.1338 (5)0.9510 (9)0.0592 (9)0.041 (2)0.50
H22A0.13950.89950.12700.049*0.50
H22B0.10531.01260.09940.049*0.50
C23A0.1937 (6)1.0044 (10)0.0109 (10)0.0510 (19)0.50
H23A0.21011.04670.05030.061*0.50
H23B0.18711.06080.07360.061*0.50
C24A0.2385 (6)0.9167 (15)0.0780 (14)0.069 (4)0.50
H24A0.27390.95710.13290.083*0.50
H24B0.25220.87200.01430.083*0.50
C25A0.2141 (4)0.8324 (6)0.1597 (9)0.060 (2)0.50
H25A0.24240.76700.18470.072*0.50
H25B0.21190.87240.23800.072*0.50
C26A0.1520 (5)0.7857 (9)0.0913 (10)0.0431 (19)0.50
H26A0.13610.74170.15230.052*0.50
H26B0.15570.73180.02380.052*0.50
C21B0.1022 (5)0.8842 (11)0.0105 (12)0.033 (2)0.50
H21B0.09270.95450.05430.040*0.50
C22B0.1328 (5)0.9275 (10)0.0865 (10)0.053 (2)0.50
H22C0.10550.98140.14540.063*0.50
H22D0.14070.86140.13670.063*0.50
C23B0.1919 (6)0.9890 (11)0.0247 (10)0.067 (3)0.50
H23C0.21071.01410.09100.080*0.50
H23D0.18391.05850.02060.080*0.50
C24B0.2341 (6)0.9105 (15)0.0671 (15)0.067 (3)0.50
H24C0.27280.95020.10440.080*0.50
H24D0.24200.84030.02280.080*0.50
C25B0.2044 (4)0.8768 (6)0.1738 (9)0.060 (2)0.50
H25C0.23190.82680.23730.073*0.50
H25D0.19600.94710.21740.073*0.50
C26B0.1456 (5)0.8122 (9)0.1134 (10)0.049 (2)0.50
H26C0.12600.79230.18010.058*0.50
H26D0.15480.73930.07560.058*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O010.0599 (8)0.0552 (8)0.0392 (6)0.0180 (6)0.0258 (6)0.0202 (6)
O020.0430 (7)0.0629 (8)0.0558 (7)0.0093 (6)0.0175 (6)0.0346 (7)
C010.0393 (8)0.0312 (8)0.0230 (7)0.0036 (6)0.0076 (6)0.0011 (6)
C020.0374 (9)0.0326 (8)0.0264 (7)0.0013 (7)0.0100 (6)0.0016 (6)
C110.0348 (8)0.0316 (8)0.0276 (7)0.0028 (6)0.0073 (6)0.0030 (6)
C120.0469 (10)0.0515 (10)0.0428 (8)0.0146 (8)0.0153 (7)0.0026 (8)
C130.0448 (10)0.0553 (11)0.0617 (10)0.0144 (8)0.0177 (8)0.0067 (9)
C140.0435 (10)0.0491 (11)0.0845 (13)0.0169 (9)0.0049 (9)0.0006 (10)
C150.0492 (11)0.0657 (12)0.0648 (11)0.0138 (9)0.0053 (9)0.0281 (10)
C160.0417 (9)0.0476 (10)0.0461 (9)0.0058 (7)0.0091 (7)0.0126 (7)
C21A0.031 (3)0.038 (4)0.022 (3)0.017 (3)0.007 (3)0.000 (2)
C22A0.041 (3)0.042 (3)0.040 (4)0.000 (2)0.012 (3)0.013 (3)
C23A0.042 (3)0.051 (3)0.063 (5)0.017 (2)0.019 (3)0.004 (3)
C24A0.037 (5)0.098 (10)0.062 (5)0.018 (5)0.002 (3)0.026 (5)
C25A0.042 (3)0.067 (5)0.062 (3)0.011 (3)0.002 (2)0.017 (4)
C26A0.037 (3)0.044 (4)0.045 (3)0.003 (2)0.007 (2)0.013 (3)
C21B0.041 (4)0.034 (4)0.024 (4)0.006 (3)0.007 (2)0.001 (2)
C22B0.041 (3)0.077 (6)0.045 (4)0.014 (3)0.019 (2)0.008 (3)
C23B0.055 (4)0.077 (6)0.072 (6)0.014 (3)0.021 (4)0.018 (5)
C24B0.035 (5)0.064 (7)0.096 (8)0.023 (4)0.010 (4)0.006 (5)
C25B0.039 (3)0.067 (5)0.064 (3)0.009 (3)0.005 (2)0.020 (4)
C26B0.037 (3)0.058 (5)0.048 (4)0.008 (3)0.008 (2)0.011 (3)
Geometric parameters (Å, º) top
O01—C011.427 (2)C12—H12B0.99
O02—C021.430 (2)C13—H13A0.99
C01—C021.524 (2)C13—H13B0.99
C01—C111.528 (2)C14—H14A0.99
C11—C121.528 (2)C14—H14B0.99
C11—C161.519 (2)C15—H15A0.99
C12—C131.519 (2)C15—H15B0.99
C13—C141.507 (2)C16—H16A0.99
C14—C151.518 (3)C16—H16B0.99
C15—C161.527 (2)C21A—H21A1.00
C02—C21A1.602 (12)C21B—H21B1.00
C02—C21B1.463 (13)C22A—H22A0.99
C21A—C22A1.534 (9)C22A—H22B0.99
C21A—C26A1.529 (10)C22B—H22C0.99
C22A—C23A1.518 (9)C22B—H22D0.99
C23A—C24A1.492 (10)C23A—H23A0.99
C24A—C25A1.535 (10)C23A—H23B0.99
C25A—C26A1.524 (9)C23B—H23C0.99
C21B—C22B1.519 (10)C23B—H23D0.99
C21B—C26B1.533 (9)C24A—H24A0.99
C22B—C23B1.525 (10)C24A—H24B0.99
C23B—C24B1.501 (10)C24B—H24C0.99
C24B—C25B1.564 (11)C24B—H24D0.99
C25B—C26B1.533 (9)C25A—H25A0.99
O01—H91A0.85 (2)C25A—H25B0.99
O01—H91B0.85 (2)C25B—H25C0.99
O02—H92A0.84 (2)C25B—H25D0.99
O02—H92B0.84 (2)C26A—H26A0.99
C01—H010.96C26A—H26B0.99
C02—H020.97C26B—H26C0.99
C11—H111.00C26B—H26D0.99
C12—H12A0.99
O01—C01—C02107.89 (11)C11—C16—H16B109.1
O01—C01—C11110.90 (11)C15—C16—H16A109.1
C02—C01—C11114.18 (10)C15—C16—H16B109.1
O02—C02—C01107.79 (11)C02—C21A—H21A109.6
O02—C02—C21A113.7 (4)C22A—C21A—H21A109.6
O02—C02—C21B108.1 (4)C26A—C21A—H21A109.6
C01—C02—C21A111.2 (4)C02—C21B—H21B106.0
C01—C02—C21B118.2 (5)C22B—C21B—H21B106.0
C01—C11—C12111.40 (11)C26B—C21B—H21B106.0
C01—C11—C16112.36 (11)C21A—C22A—H22A109.5
C12—C11—C16110.30 (12)C21A—C22A—H22B109.5
C11—C12—C13112.38 (12)C23A—C22A—H22A109.5
C12—C13—C14111.23 (14)C23A—C22A—H22B109.5
C13—C14—C15110.51 (14)C21B—C22B—H22C109.2
C14—C15—C16112.05 (14)C21B—C22B—H22D109.2
C11—C16—C15112.38 (13)C23B—C22B—H22C109.2
C02—C21A—C22A109.8 (9)C23B—C22B—H22D109.2
C02—C21A—C26A109.5 (8)C22A—C23A—H23A109.1
C22A—C21A—C26A108.6 (8)C22A—C23A—H23B109.1
C21A—C22A—C23A110.6 (8)C24A—C23A—H23A109.1
C22A—C23A—C24A112.6 (9)C24A—C23A—H23B109.1
C23A—C24A—C25A113.7 (9)C22B—C23B—H23C109.5
C24A—C25A—C26A112.9 (8)C22B—C23B—H23D109.5
C21A—C26A—C25A112.3 (8)C24B—C23B—H23C109.5
C02—C21B—C22B114.7 (10)C24B—C23B—H23D109.5
C02—C21B—C26B112.6 (8)C23A—C24A—H24A108.8
C22B—C21B—C26B110.9 (8)C23A—C24A—H24B108.8
C21B—C22B—C23B112.3 (9)C25A—C24A—H24A108.8
C22B—C23B—C24B110.7 (10)C25A—C24A—H24B108.8
C23B—C24B—C25B108.3 (9)C23B—C24B—H24C110.0
C24B—C25B—C26B108.7 (8)C23B—C24B—H24D110.0
C21B—C26B—C25B112.1 (8)C25B—C24B—H24C110.0
C01—O01—H91A119 (2)C25B—C24B—H24D110.0
C01—O01—H91B118 (3)C24A—C25A—H25A109.0
H91A—O01—H91B107 (3)C24A—C25A—H25B109.0
C02—O02—H92A114 (2)C26A—C25A—H25A109.0
C02—O02—H92B137 (3)C26A—C25A—H25B109.0
H92A—O02—H92B95 (3)C24B—C25B—H25C110.0
O01—C01—H01105.1C24B—C25B—H25D110.0
C02—C01—H01109.2C26B—C25B—H25C110.0
C11—C01—H01109.1C26B—C25B—H25D110.0
O02—C02—H02107.3C21A—C26A—H26A109.1
C01—C02—H02108.7C21A—C26A—H26B109.1
C21A—C02—H02108.0C25A—C26A—H26A109.1
C21B—C02—H02106.4C25A—C26A—H26B109.1
C01—C11—H11107.5C21B—C26B—H26C109.2
C12—C11—H11107.5C21B—C26B—H26D109.2
C16—C11—H11107.5C25B—C26B—H26C109.2
C11—C12—H12A109.1C25B—C26B—H26D109.2
C11—C12—H12B109.1H12A—C12—H12B107.9
C13—C12—H12A109.1H13A—C13—H13B108.0
C13—C12—H12B109.1H14A—C14—H14B108.1
C12—C13—H13A109.4H15A—C15—H15B107.9
C12—C13—H13B109.4H16A—C16—H16B107.9
C14—C13—H13A109.4H22A—C22A—H22B108.1
C14—C13—H13B109.4H22C—C22B—H22D107.9
C13—C14—H14A109.5H23A—C23A—H23B107.8
C13—C14—H14B109.5H23C—C23B—H23D108.1
C15—C14—H14A109.5H24A—C24A—H24B107.7
C15—C14—H14B109.5H24C—C24B—H24D108.4
C14—C15—H15A109.2H25A—C25A—H25B107.8
C14—C15—H15B109.2H25C—C25B—H25D108.3
C16—C15—H15A109.2H26A—C26A—H26B107.9
C16—C15—H15B109.2H26C—C26B—H26D107.9
C11—C16—H16A109.1
O01—C01—C02—O0273.24 (14)C01—C02—C21A—C22A168.1 (7)
C11—C01—C02—O0250.53 (16)C26A—C21A—C22A—C23A60.2 (12)
O01—C01—C02—C21B49.5 (6)C02—C21A—C22A—C23A179.9 (8)
C11—C01—C02—C21B173.3 (5)C21A—C22A—C23A—C24A57.2 (13)
O01—C01—C02—C21A52.0 (5)C22A—C23A—C24A—C25A49.4 (16)
C11—C01—C02—C21A175.8 (5)C23A—C24A—C25A—C26A45.8 (16)
O01—C01—C11—C16179.55 (11)C24A—C25A—C26A—C21A50.3 (12)
C02—C01—C11—C1657.41 (16)C22A—C21A—C26A—C25A57.3 (12)
O01—C01—C11—C1256.11 (16)C02—C21A—C26A—C25A177.2 (8)
C02—C01—C11—C12178.25 (12)O02—C02—C21B—C22B58.3 (10)
C16—C11—C12—C1353.85 (18)C01—C02—C21B—C22B179.0 (7)
C01—C11—C12—C13179.34 (13)O02—C02—C21B—C26B173.6 (7)
C11—C12—C13—C1456.57 (19)C01—C02—C21B—C26B51.0 (10)
C12—C13—C14—C1556.27 (19)C02—C21B—C22B—C23B179.2 (9)
C13—C14—C15—C1655.2 (2)C26B—C21B—C22B—C23B51.9 (14)
C12—C11—C16—C1552.32 (18)C21B—C22B—C23B—C24B57.9 (13)
C01—C11—C16—C15177.26 (13)C22B—C23B—C24B—C25B61.7 (14)
C14—C15—C16—C1154.0 (2)C23B—C24B—C25B—C26B61.4 (13)
O02—C02—C21A—C26A165.4 (6)C24B—C25B—C26B—C21B57.4 (10)
C21B—C02—C21A—C26A125 (8)C02—C21B—C26B—C25B177.2 (8)
C01—C02—C21A—C26A72.7 (9)C22B—C21B—C26B—C25B52.8 (12)
O02—C02—C21A—C22A46.3 (10)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O01—H91A···O01i0.85 (2)1.85 (2)2.652 (2)155 (3)
O01—H91B···O02ii0.85 (2)1.93 (2)2.665 (2)145 (3)
O02—H92A···O02iii0.84 (2)1.81 (2)2.636 (2)166 (4)
O02—H92B···O01ii0.84 (2)1.83 (2)2.665 (2)170 (4)
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+2, z; (iii) x, y, z1/2.

Experimental details

(k98005)(k00009)(k98064)(k00013)
Crystal data
Chemical formulaC14H26O2C14H26O2C14H26O2C14H26O2
Mr226.35226.35226.35226.35
Crystal system, space groupMonoclinic, P1211Monoclinic, P1211Monoclinic, C12/c1Monoclinic, C12/c1
Temperature (K)295173295173
a, b, c (Å)5.540 (1), 41.653 (6), 12.025 (2)5.4816 (6), 41.262 (6), 11.954 (2)23.153 (5), 11.852 (3), 10.926 (2)23.161 (5), 11.584 (3), 10.973 (2)
β (°) 90.33 (1) 90.39 (1) 104.64 (2) 106.10 (2)
V3)2774.8 (8)2703.7 (7)2900.9 (11)2828.6 (11)
Z8888
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.070.070.070.07
Crystal size (mm)0.50 × 0.32 × 0.250.44 × 0.20 × 0.160.31 × 0.22 × 0.130.56 × 0.55 × 0.10
Data collection
DiffractometerNonius Kappa-CCD
diffractometer
Nonius Kappa-CCD
diffractometer
Nonius Kappa-CCD
diffractometer
Nonius Kappa-CCD
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
9310, 4928, 3636 8305, 4720, 3750 4869, 2529, 1942 4693, 2489, 1911
Rint0.0470.0340.0230.021
(sin θ/λ)max1)0.5950.5950.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.144, 1.09 0.042, 0.089, 1.03 0.068, 0.208, 1.13 0.047, 0.118, 1.06
No. of reflections4928472025292489
No. of parameters610609211211
No. of restraints116464
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.110.12, 0.150.14, 0.120.15, 0.19

Computer programs: COLLECT software (Nonius, 1998), DENZO-SMN (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare, Cascarano, Giacovazzo, Guagliardi, Burla, Polidori & Camalli, 1994) in maXus (Mackay, Gilmore, Edwards, Tremayne, Stewart & Shankland, 1998), SHELXL97 (Sheldrick, 1997), SHELXTL PC (Sheldrick, 1990).

Hydrogen-bond geometry (Å, º) for (k98005) top
D—H···AD—HH···AD···AD—H···A
O01A—H01A···O02Ai1.01 (8)1.76 (8)2.760 (4)174 (6)
O01B—H01B···O02Bii0.73 (4)1.98 (5)2.704 (4)168 (4)
O01C—H01C···O02Ci0.82 (5)1.95 (5)2.759 (4)167 (4)
O01D—H01D···O02Dii0.83 (5)1.86 (5)2.682 (4)176 (5)
O02A—H02A···O01B0.79 (6)1.95 (6)2.717 (5)163 (6)
O02B—H02B···O01A0.81 (5)1.98 (5)2.746 (5)158 (4)
O02C—H02C···O01D0.87 (6)1.90 (6)2.725 (5)158 (5)
O02D—H02D···O01C0.72 (6)2.15 (6)2.731 (5)140 (6)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) for (k00009) top
D—H···AD—HH···AD···AD—H···A
O01A—H01A···O02Ai0.90 (4)1.83 (4)2.724 (2)170 (4)
O01B—H01B···O02Bii0.95 (3)1.72 (3)2.656 (3)169 (3)
O01C—H01C···O02Ci0.93 (4)1.80 (4)2.730 (2)172 (3)
O01D—H01D···O02Dii0.85 (3)1.81 (3)2.658 (3)174 (3)
O02A—H02A···O01B1.05 (5)1.66 (5)2.682 (3)161 (4)
O02B—H02B···O01A0.95 (4)1.87 (4)2.727 (3)149 (3)
O02C—H02C···O01D0.97 (4)1.78 (4)2.698 (3)157 (3)
O02D—H02D···O01C0.91 (5)1.88 (5)2.717 (3)152 (4)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z.
Hydrogen-bond geometry (Å, º) for (k98064) top
D—H···AD—HH···AD···AD—H···A
O01—H91A···O01i0.84 (2)1.87 (2)2.641 (3)152 (5)
O01—H91B···O02ii0.84 (2)1.91 (3)2.682 (3)153 (6)
O02—H92A···O02iii0.83 (2)1.86 (2)2.654 (3)160 (5)
O02—H92B···O01ii0.84 (2)2.01 (4)2.682 (3)138 (5)
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+2, z; (iii) x, y, z1/2.
Hydrogen-bond geometry (Å, º) for (k00013) top
D—H···AD—HH···AD···AD—H···A
O01—H91A···O01i0.85 (2)1.85 (2)2.652 (2)155 (3)
O01—H91B···O02ii0.85 (2)1.93 (2)2.665 (2)145 (3)
O02—H92A···O02iii0.84 (2)1.81 (2)2.636 (2)166 (4)
O02—H92B···O01ii0.84 (2)1.83 (2)2.665 (2)170 (4)
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+2, z; (iii) x, y, z1/2.
 

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