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A 1:1 co-crystal of rac-trans-1,2-C6H10(OH)2 and (C6H5)3PO has been found that is unusual because there are no strong interactions between the two kinds of molecules, which are segregated into layers. Furthermore, neither pure rac-1,2-cyclohexanediol (CHD) nor pure triphenylphosphine oxide (TPPO) has any obvious packing problem that would make the formation of inclusion complexes likely. The TPPO layers are very much like those found in two of the four known polymorphs of pure TPPO. The hydrogen-bonded ribbons of CHD are similar to those found in other vic-diol crystals. The co-crystals are triclinic (space group P\overline 1), but the deviations from monoclinic symmetry (space group C2/c) are small. The magnitudes of those deviations depend on the solvent from which the crystal is grown; the deviations are largest for crystals grown from acetone, smallest for crystals grown from toluene, and intermediate for crystals grown from ethanol. The deviations arise from incomplete enantiomeric disorder of the R,R and S,S diols; this disorder is not required by symmetry in either space group, but occupancy factors are nearly 0.50 when the structure is refined as monoclinic. When the structure is refined as triclinic the deviations of the occupancy factors from 0.50 mirror the deviations from monoclinic symmetry because information about the partial R,R/S,S ordering is transmitted from one diol layer to the next through the very pseudosymmetric TPPO layer. Analyses suggest individual CHD layers are at least mostly ordered. The degree of order seems to be established at the time the crystal is grown and is unlikely to change with heating or cooling. Thermal data suggest the existence of the co-crystal is a consequence of kinetic rather than thermodynamic factors.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768107054699/de5032sup1.cif
Contains datablocks acetone90Ktri, ethanol90Ktri, toluene90KtriCuKa, acetone90Kmono, ethanol90Kmono, toluene90KmonoCuKa, acetone294Ktri, ethanol294Ktri, toluene294Ktri, acetone294Kmono, ethanol294Kmono, toluene294Kmono

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032acetone90Ktrisup2.hkl
Contains datablock acetone90Ktri

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032ethanol90Ktrisup3.hkl
Contains datablock ethanol90Ktri

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032toluene90KtriCuKasup4.hkl
Contains datablock toluene90KtriCuKa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032acetone90Kmonosup5.hkl
Contains datablock acetone90Kmono

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032ethanol90Kmonosup6.hkl
Contains datablock ethanol90Kmono

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032toluene90KmonoCuKasup7.hkl
Contains datablock toluene90KmonoCuKa

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032acetone294Ktrisup8.hkl
Contains datablock acetone294Ktri

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032ethanol294Ktrisup9.hkl
Contains datablock ethanol294Ktri

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032toluene294Ktrisup10.hkl
Contains datablock toluene294Ktri

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032acetone294Kmonosup11.hkl
Contains datablock acetone294Kmono

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032ethanol294Kmonosup12.hkl
Contains datablock ethanol294Kmono

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768107054699/de5032toluene294Kmonosup13.hkl
Contains datablock toluene294Kmono

CCDC references: 671615; 671616; 671617; 671618; 671619; 671620; 671621; 671622; 671623; 671624; 671625; 671626

Computing details top

Data collection: COLLECT (Nonius, 1999) for acetone90Ktri, ethanol90Ktri, acetone90Kmono, ethanol90Kmono, acetone294Ktri, ethanol294Ktri, toluene294Ktri, acetone294Kmono, ethanol294Kmono, toluene294Kmono; APEX2 (Bruker-Nonius, 2004) for toluene90KtriCuKa, toluene90KmonoCuKa. Cell refinement: SCALEPACK (Otwinowski & Minor, 1997) for acetone90Ktri, ethanol90Ktri, acetone90Kmono, ethanol90Kmono, acetone294Ktri, ethanol294Ktri, toluene294Ktri, acetone294Kmono, ethanol294Kmono, toluene294Kmono; Saintplus in APEX2 (Bruker-Nonius,2004) for toluene90KtriCuKa, toluene90KmonoCuKa. Data reduction: DENZO-SMN (Otwinowski & Minor, 1997) for acetone90Ktri, ethanol90Ktri, acetone90Kmono, ethanol90Kmono, acetone294Ktri, ethanol294Ktri, toluene294Ktri, acetone294Kmono, ethanol294Kmono, toluene294Kmono; Saintplus in APEX2 (Bruker-Nonius,2004) for toluene90KtriCuKa, toluene90KmonoCuKa. For all compounds, program(s) used to solve structure: MULTAN (Main et al., 1977) and DIRDIF (Beurskens, et al., 1983); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997). Molecular graphics: Mercury (Macrae et al., 2006) for acetone90Ktri, ethanol90Ktri, toluene90KtriCuKa, acetone90Kmono, ethanol90Kmono, acetone294Ktri, ethanol294Ktri, toluene294Ktri, acetone294Kmono, ethanol294Kmono, toluene294Kmono; Mercury (Bruno et al., 2002) for toluene90KmonoCuKa. For all compounds, software used to prepare material for publication: SHELXL97 (Sheldrick, 1997) and local procedures.

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
[Figure 11]
(acetone90Ktri) 1:1 rac-1,2-cyclohexanediol triphenylphosphine oxide top
Crystal data top
C6H12O2·C18H15OPZ = 4
Mr = 394.43F(000) = 840
Triclinic, P1Dx = 1.270 Mg m3
a = 9.276 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.913 (1) ÅCell parameters from 9276 reflections
c = 21.256 (2) Åθ = 1.0–27.5°
α = 100.58 (1)°µ = 0.16 mm1
β = 102.52 (1)°T = 90 K
γ = 90.51 (1)°Lath, colorless
V = 2062.2 (4) Å30.25 × 0.21 × 0.13 mm
Data collection top
Nonius KappaCCD
diffractometer
7244 independent reflections
Radiation source: fine-focus sealed tube4848 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.052
Detector resolution: 10 pixels mm-1θmax = 25.0°, θmin = 1.0°
1.0° ω scans at fixed χ = 55°h = 1111
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
k = 1212
Tmin = 0.96, Tmax = 0.98l = 2525
14392 measured 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0595P)2]
where P = (Fo2 + 2Fc2)/3
7244 reflections(Δ/σ)max = 0.001
564 parametersΔρmax = 0.35 e Å3
148 restraintsΔρmin = 0.29 e Å3
Crystal data top
C6H12O2·C18H15OPγ = 90.51 (1)°
Mr = 394.43V = 2062.2 (4) Å3
Triclinic, P1Z = 4
a = 9.276 (1) ÅMo Kα radiation
b = 10.913 (1) ŵ = 0.16 mm1
c = 21.256 (2) ÅT = 90 K
α = 100.58 (1)°0.25 × 0.21 × 0.13 mm
β = 102.52 (1)°
Data collection top
Nonius KappaCCD
diffractometer
7244 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
4848 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.98Rint = 0.052
14392 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049148 restraints
wR(F2) = 0.122H-atom parameters constrained
S = 1.06Δρmax = 0.35 e Å3
7244 reflectionsΔρmin = 0.29 e Å3
564 parameters
Special details top

Experimental. The crystal-to-detector distance was 40 mm. Each frame was measured for 20 s. The number of scan sets measured was 9; the total number of frames measured was 951.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.7776 (4)0.0767 (3)0.03766 (19)0.0236 (10)0.800 (5)
H1A0.82950.05870.00060.028*0.800 (5)
C2A0.7472 (4)0.0446 (3)0.05813 (19)0.0224 (10)0.800 (5)
H2A0.69160.02770.09400.027*0.800 (5)
C3A0.8914 (4)0.1032 (4)0.0832 (2)0.0300 (12)0.800 (5)
H3A10.94340.12620.04700.036*0.800 (5)
H3A20.86990.18030.09860.036*0.800 (5)
C4A0.9910 (4)0.0123 (4)0.1397 (2)0.0321 (13)0.800 (5)
H4A10.94320.00400.17750.038*0.800 (5)
H4A21.08620.05050.15360.038*0.800 (5)
C5A1.0201 (4)0.1107 (4)0.1190 (2)0.0320 (11)0.800 (5)
H5A11.07920.16980.15710.038*0.800 (5)
H5A21.07740.09600.08430.038*0.800 (5)
C6A0.8746 (5)0.1667 (4)0.0935 (3)0.0280 (12)0.800 (5)
H6A10.82210.18860.12960.034*0.800 (5)
H6A20.89460.24430.07830.034*0.800 (5)
O1A0.6372 (4)0.1262 (4)0.01440 (18)0.0293 (10)0.800 (5)
H1A10.65080.19630.00500.044*0.800 (5)
O2A0.6606 (4)0.1323 (4)0.00368 (17)0.0309 (10)0.800 (5)
H2A10.57230.11170.00350.046*0.800 (5)
C1A'0.7476 (13)0.0805 (11)0.0579 (6)0.0236 (10)0.200 (5)
H1A'0.68750.09290.09220.028*0.200 (5)
C2A'0.7766 (13)0.0565 (11)0.0417 (6)0.0224 (10)0.200 (5)
H2A'0.83150.07050.00550.027*0.200 (5)
C3A'0.8686 (17)0.0982 (12)0.1020 (8)0.0300 (12)0.200 (5)
H3A30.88890.18750.09090.036*0.200 (5)
H3A40.81290.08800.13730.036*0.200 (5)
C4A'1.0150 (15)0.0198 (14)0.1261 (10)0.0321 (13)0.200 (5)
H4A31.07430.04660.16540.038*0.200 (5)
H4A41.07250.03250.09150.038*0.200 (5)
C5A'0.9841 (15)0.1181 (13)0.1430 (7)0.0320 (11)0.200 (5)
H5A30.93210.13160.17960.038*0.200 (5)
H5A41.07870.16860.15750.038*0.200 (5)
C6A'0.890 (2)0.1595 (13)0.0838 (11)0.0280 (12)0.200 (5)
H6A30.86690.24790.09610.034*0.200 (5)
H6A40.94620.15350.04880.034*0.200 (5)
O1A'0.6633 (18)0.1158 (17)0.0006 (7)0.0293 (10)0.200 (5)
H1A20.57960.07820.01120.044*0.200 (5)
O2A'0.6402 (16)0.1319 (15)0.0214 (8)0.0309 (10)0.200 (5)
H2A20.65890.20770.01840.046*0.200 (5)
C1B0.3083 (4)0.5897 (3)0.05224 (16)0.0220 (9)0.882 (6)
H1B0.40500.60760.08480.026*0.882 (6)
C2B0.2690 (4)0.4523 (3)0.04029 (17)0.0252 (9)0.882 (6)
H2B0.17430.43370.00650.030*0.882 (6)
C3B0.2485 (4)0.4135 (3)0.10300 (18)0.0325 (10)0.882 (6)
H3B10.34320.42730.13610.039*0.882 (6)
H3B20.21930.32340.09390.039*0.882 (6)
C4B0.1298 (6)0.4886 (4)0.1302 (2)0.0368 (11)0.882 (6)
H4B10.03300.46780.09900.044*0.882 (6)
H4B20.12210.46550.17230.044*0.882 (6)
C5B0.1665 (5)0.6280 (3)0.14104 (18)0.0342 (10)0.882 (6)
H5B10.08410.67430.15520.041*0.882 (6)
H5B20.25640.65030.17650.041*0.882 (6)
C6B0.1919 (5)0.6664 (3)0.0795 (2)0.0278 (10)0.882 (6)
H6B10.22420.75590.08940.033*0.882 (6)
H6B20.09790.65530.04590.033*0.882 (6)
O1B0.3227 (3)0.6289 (3)0.00719 (14)0.0292 (8)0.882 (6)
H1B10.40120.60300.01730.044*0.882 (6)
O2B0.3842 (5)0.3872 (3)0.0151 (2)0.0312 (11)0.882 (6)
H2B10.36240.31020.00620.047*0.882 (6)
C1B'0.264 (2)0.5714 (17)0.0357 (9)0.0220 (9)0.118 (6)
H1B'0.17530.54900.00130.026*0.118 (6)
C2B'0.317 (2)0.4541 (17)0.0591 (10)0.0252 (9)0.118 (6)
H2B'0.40790.47570.09510.030*0.118 (6)
C3B'0.199 (3)0.3943 (18)0.0851 (13)0.0325 (10)0.118 (6)
H3B30.23780.31960.10210.039*0.118 (6)
H3B40.11170.36710.04890.039*0.118 (6)
C4B'0.154 (4)0.486 (3)0.1399 (15)0.0368 (11)0.118 (6)
H4B30.07170.44750.15380.044*0.118 (6)
H4B40.23810.50540.17820.044*0.118 (6)
C5B'0.104 (3)0.606 (2)0.1174 (12)0.0342 (10)0.118 (6)
H5B30.01160.58890.08300.041*0.118 (6)
H5B40.08330.66660.15480.041*0.118 (6)
C6B'0.220 (3)0.6637 (17)0.0904 (15)0.0278 (10)0.118 (6)
H6B30.30890.69070.12620.033*0.118 (6)
H6B40.18210.73830.07340.033*0.118 (6)
O1B'0.376 (2)0.631 (2)0.0125 (11)0.0292 (8)0.118 (6)
H1B20.35180.70290.00780.044*0.118 (6)
O2B'0.355 (4)0.372 (2)0.0048 (17)0.0312 (11)0.118 (6)
H2B20.30720.38920.03060.047*0.118 (6)
P01A0.78901 (8)0.16348 (7)0.33676 (3)0.0217 (2)
O11A0.84600 (19)0.29351 (16)0.34207 (9)0.0246 (5)
C11A0.6337 (3)0.1192 (3)0.26797 (13)0.0200 (7)
C12A0.6201 (3)0.1851 (3)0.21668 (13)0.0238 (7)
H12A0.68880.25210.21970.029*
C13A0.5068 (3)0.1530 (3)0.16152 (14)0.0290 (7)
H13A0.49780.19820.12680.035*
C14A0.4066 (3)0.0554 (3)0.15669 (14)0.0311 (8)
H14A0.32950.03290.11850.037*
C15A0.4184 (3)0.0092 (3)0.20722 (14)0.0268 (7)
H15A0.34910.07610.20360.032*
C16A0.5309 (3)0.0223 (3)0.26368 (13)0.0227 (7)
H16A0.53730.02170.29870.027*
C21A0.7268 (3)0.1362 (3)0.40760 (13)0.0216 (7)
C22A0.6082 (3)0.2025 (3)0.42441 (14)0.0302 (7)
H22A0.55910.25600.39700.036*
C23A0.5616 (4)0.1907 (3)0.48084 (15)0.0370 (8)
H23A0.48060.23590.49180.044*
C24A0.6327 (3)0.1134 (3)0.52118 (14)0.0325 (8)
H24A0.60200.10700.56030.039*
C25A0.7477 (3)0.0457 (3)0.50460 (15)0.0333 (8)
H25A0.79520.00900.53170.040*
C26A0.7945 (3)0.0577 (3)0.44773 (14)0.0291 (7)
H26A0.87420.01100.43650.035*
C31A0.9278 (3)0.0522 (3)0.32451 (13)0.0216 (7)
C32A1.0756 (3)0.0960 (3)0.34198 (13)0.0245 (7)
H32A1.10030.18130.36140.029*
C33A1.1868 (3)0.0160 (3)0.33121 (13)0.0286 (7)
H33A1.28700.04690.34250.034*
C34A1.1522 (3)0.1085 (3)0.30404 (13)0.0277 (7)
H34A1.22830.16310.29650.033*
C35A1.0061 (3)0.1535 (3)0.28784 (13)0.0282 (7)
H35A0.98230.23950.27010.034*
C36A0.8944 (3)0.0730 (3)0.29752 (13)0.0262 (7)
H36A0.79430.10410.28550.031*
P01B0.55005 (8)0.66143 (7)0.33453 (3)0.0209 (2)
O11B0.50019 (19)0.79079 (16)0.34043 (9)0.0243 (5)
C11B0.6399 (3)0.6211 (2)0.26659 (13)0.0201 (7)
C12B0.6061 (3)0.6895 (3)0.21650 (13)0.0218 (7)
H12B0.54030.75540.21950.026*
C13B0.6690 (3)0.6613 (3)0.16206 (14)0.0305 (8)
H13B0.64760.70910.12840.037*
C14B0.7617 (3)0.5645 (3)0.15695 (15)0.0320 (8)
H14B0.80220.54390.11920.038*
C15B0.7965 (3)0.4969 (3)0.20690 (14)0.0275 (7)
H15B0.86190.43080.20330.033*
C16B0.7369 (3)0.5248 (2)0.26217 (13)0.0231 (7)
H16B0.76200.47870.29650.028*
C21B0.6804 (3)0.6334 (3)0.40574 (13)0.0209 (7)
C22B0.8169 (3)0.6996 (3)0.42326 (14)0.0311 (8)
H22B0.84090.75350.39620.037*
C23B0.9178 (3)0.6870 (3)0.48018 (15)0.0372 (8)
H23B1.01050.73250.49190.045*
C24B0.8846 (3)0.6089 (3)0.51982 (14)0.0320 (8)
H24B0.95360.60130.55890.038*
C25B0.7507 (3)0.5421 (3)0.50236 (14)0.0343 (8)
H25B0.72760.48730.52910.041*
C26B0.6492 (3)0.5549 (3)0.44552 (13)0.0295 (7)
H26B0.55690.50880.43390.035*
C31B0.3969 (3)0.5487 (3)0.32053 (13)0.0206 (7)
C32B0.2688 (3)0.5895 (3)0.33918 (13)0.0230 (7)
H32B0.26470.67400.35960.028*
C33B0.1460 (3)0.5078 (3)0.32830 (13)0.0285 (7)
H33B0.05800.53690.34050.034*
C34B0.1525 (3)0.3848 (3)0.29977 (14)0.0304 (8)
H34B0.06870.32910.29210.037*
C35B0.2804 (3)0.3421 (3)0.28219 (14)0.0309 (8)
H35B0.28500.25680.26310.037*
C36B0.4026 (3)0.4239 (3)0.29239 (13)0.0264 (7)
H36B0.49040.39440.28010.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0170 (19)0.0293 (16)0.026 (2)0.0048 (14)0.0076 (15)0.0058 (16)
C2A0.0180 (19)0.0255 (17)0.023 (2)0.0009 (13)0.0063 (15)0.0017 (15)
C3A0.023 (2)0.0342 (18)0.036 (3)0.0029 (14)0.0068 (17)0.0143 (18)
C4A0.024 (2)0.046 (2)0.027 (3)0.0037 (16)0.0032 (17)0.0121 (18)
C5A0.022 (2)0.0397 (19)0.032 (3)0.0014 (16)0.0029 (17)0.0049 (19)
C6A0.0222 (18)0.0277 (18)0.033 (2)0.0006 (13)0.0078 (17)0.0014 (16)
O1A0.0190 (17)0.0282 (15)0.041 (2)0.0065 (12)0.0038 (14)0.0098 (16)
O2A0.0224 (15)0.0292 (13)0.037 (2)0.0023 (11)0.0016 (14)0.0027 (15)
C1A'0.0170 (19)0.0293 (16)0.026 (2)0.0048 (14)0.0076 (15)0.0058 (16)
C2A'0.0180 (19)0.0255 (17)0.023 (2)0.0009 (13)0.0063 (15)0.0017 (15)
C3A'0.023 (2)0.0342 (18)0.036 (3)0.0029 (14)0.0068 (17)0.0143 (18)
C4A'0.024 (2)0.046 (2)0.027 (3)0.0037 (16)0.0032 (17)0.0121 (18)
C5A'0.022 (2)0.0397 (19)0.032 (3)0.0014 (16)0.0029 (17)0.0049 (19)
C6A'0.0222 (18)0.0277 (18)0.033 (2)0.0006 (13)0.0078 (17)0.0014 (16)
O1A'0.0190 (17)0.0282 (15)0.041 (2)0.0065 (12)0.0038 (14)0.0098 (16)
O2A'0.0224 (15)0.0292 (13)0.037 (2)0.0023 (11)0.0016 (14)0.0027 (15)
C1B0.020 (2)0.0238 (16)0.021 (2)0.0021 (14)0.0032 (16)0.0034 (14)
C2B0.021 (2)0.0243 (15)0.032 (2)0.0056 (15)0.0106 (18)0.0049 (15)
C3B0.032 (2)0.033 (2)0.040 (3)0.0095 (17)0.0164 (19)0.0158 (18)
C4B0.037 (3)0.0452 (19)0.037 (2)0.0115 (17)0.020 (2)0.0171 (17)
C5B0.034 (2)0.041 (2)0.030 (2)0.0108 (18)0.0138 (18)0.0030 (18)
C6B0.025 (2)0.0228 (16)0.035 (2)0.0028 (14)0.0087 (19)0.0013 (14)
O1B0.0287 (18)0.0278 (13)0.0371 (19)0.0048 (13)0.0167 (14)0.0105 (13)
O2B0.031 (2)0.0245 (14)0.043 (2)0.0056 (13)0.0186 (19)0.0058 (13)
C1B'0.020 (2)0.0238 (16)0.021 (2)0.0021 (14)0.0032 (16)0.0034 (14)
C2B'0.021 (2)0.0243 (15)0.032 (2)0.0056 (15)0.0106 (18)0.0049 (15)
C3B'0.032 (2)0.033 (2)0.040 (3)0.0095 (17)0.0164 (19)0.0158 (18)
C4B'0.037 (3)0.0452 (19)0.037 (2)0.0115 (17)0.020 (2)0.0171 (17)
C5B'0.034 (2)0.041 (2)0.030 (2)0.0108 (18)0.0138 (18)0.0030 (18)
C6B'0.025 (2)0.0228 (16)0.035 (2)0.0028 (14)0.0087 (19)0.0013 (14)
O1B'0.0287 (18)0.0278 (13)0.0371 (19)0.0048 (13)0.0167 (14)0.0105 (13)
O2B'0.031 (2)0.0245 (14)0.043 (2)0.0056 (13)0.0186 (19)0.0058 (13)
P01A0.0188 (4)0.0240 (5)0.0222 (4)0.0021 (3)0.0049 (3)0.0042 (3)
O11A0.0242 (11)0.0202 (11)0.0289 (12)0.0016 (9)0.0047 (9)0.0053 (9)
C11A0.0150 (15)0.0239 (17)0.0212 (16)0.0063 (12)0.0078 (12)0.0005 (13)
C12A0.0209 (16)0.0262 (18)0.0267 (18)0.0055 (13)0.0120 (14)0.0028 (14)
C13A0.0304 (18)0.0343 (19)0.0231 (18)0.0086 (15)0.0067 (14)0.0067 (14)
C14A0.0186 (17)0.047 (2)0.0225 (18)0.0061 (15)0.0017 (13)0.0016 (16)
C15A0.0164 (16)0.0286 (18)0.0333 (19)0.0000 (13)0.0030 (14)0.0036 (15)
C16A0.0183 (16)0.0261 (17)0.0252 (17)0.0057 (13)0.0076 (13)0.0053 (13)
C21A0.0196 (15)0.0223 (17)0.0198 (16)0.0046 (13)0.0016 (13)0.0008 (13)
C22A0.0359 (19)0.0270 (18)0.0290 (18)0.0097 (14)0.0103 (15)0.0048 (14)
C23A0.040 (2)0.039 (2)0.033 (2)0.0056 (16)0.0192 (16)0.0026 (17)
C24A0.0374 (19)0.038 (2)0.0220 (18)0.0079 (16)0.0112 (15)0.0013 (15)
C25A0.0335 (19)0.038 (2)0.0299 (19)0.0033 (15)0.0058 (15)0.0118 (15)
C26A0.0249 (17)0.0359 (19)0.0289 (18)0.0022 (14)0.0099 (14)0.0075 (15)
C31A0.0220 (16)0.0252 (17)0.0176 (16)0.0029 (13)0.0030 (13)0.0056 (13)
C32A0.0241 (17)0.0296 (18)0.0210 (17)0.0019 (14)0.0052 (13)0.0073 (14)
C33A0.0214 (16)0.038 (2)0.0300 (18)0.0031 (14)0.0072 (14)0.0145 (15)
C34A0.0248 (17)0.034 (2)0.0283 (18)0.0120 (14)0.0114 (14)0.0103 (15)
C35A0.0314 (18)0.0244 (18)0.0305 (18)0.0055 (14)0.0098 (15)0.0060 (14)
C36A0.0188 (16)0.0328 (19)0.0276 (18)0.0030 (14)0.0057 (13)0.0067 (15)
P01B0.0184 (4)0.0227 (4)0.0219 (4)0.0016 (3)0.0057 (3)0.0039 (3)
O11B0.0238 (11)0.0211 (11)0.0286 (11)0.0029 (9)0.0081 (9)0.0038 (9)
C11B0.0143 (15)0.0247 (17)0.0187 (16)0.0045 (12)0.0010 (12)0.0012 (13)
C12B0.0147 (15)0.0280 (18)0.0229 (17)0.0012 (12)0.0036 (13)0.0056 (14)
C13B0.0236 (17)0.046 (2)0.0205 (17)0.0041 (15)0.0014 (14)0.0077 (15)
C14B0.0214 (17)0.046 (2)0.0248 (18)0.0076 (15)0.0068 (14)0.0034 (16)
C15B0.0201 (16)0.0308 (19)0.0306 (19)0.0032 (13)0.0092 (14)0.0014 (15)
C16B0.0180 (15)0.0232 (17)0.0264 (17)0.0006 (13)0.0032 (13)0.0025 (14)
C21B0.0223 (16)0.0217 (16)0.0191 (16)0.0029 (13)0.0080 (13)0.0009 (13)
C22B0.0307 (19)0.0322 (19)0.0296 (19)0.0046 (15)0.0039 (15)0.0077 (15)
C23B0.0286 (18)0.035 (2)0.039 (2)0.0050 (15)0.0040 (16)0.0015 (17)
C24B0.0354 (19)0.035 (2)0.0218 (17)0.0099 (15)0.0004 (15)0.0019 (15)
C25B0.0346 (19)0.043 (2)0.0276 (18)0.0037 (16)0.0052 (15)0.0133 (16)
C26B0.0239 (17)0.038 (2)0.0275 (18)0.0009 (14)0.0054 (14)0.0084 (15)
C31B0.0184 (15)0.0263 (17)0.0170 (16)0.0020 (13)0.0031 (12)0.0048 (13)
C32B0.0244 (17)0.0261 (17)0.0210 (16)0.0049 (14)0.0061 (13)0.0096 (13)
C33B0.0180 (16)0.042 (2)0.0295 (18)0.0040 (15)0.0076 (14)0.0136 (16)
C34B0.0194 (17)0.041 (2)0.0324 (19)0.0057 (14)0.0023 (14)0.0159 (16)
C35B0.0305 (19)0.0305 (19)0.0320 (19)0.0041 (15)0.0061 (15)0.0081 (15)
C36B0.0192 (16)0.0303 (18)0.0305 (18)0.0029 (14)0.0075 (14)0.0053 (14)
Geometric parameters (Å, º) top
C1A—O1A1.436 (4)C6B'—H6B40.9900
C1A—C6A1.509 (5)O1B'—H1B20.8400
C1A—C2A1.510 (4)O2B'—H2B20.8400
C1A—H1A1.0000P01A—O11A1.4858 (19)
C2A—O2A1.441 (4)P01A—C21A1.796 (3)
C2A—C3A1.521 (4)P01A—C31A1.804 (3)
C2A—H2A1.0000P01A—C11A1.806 (3)
C3A—C4A1.531 (5)C11A—C16A1.395 (4)
C3A—H3A10.9900C11A—C12A1.397 (4)
C3A—H3A20.9900C12A—C13A1.382 (4)
C4A—C5A1.526 (4)C12A—H12A0.9500
C4A—H4A10.9900C13A—C14A1.382 (4)
C4A—H4A20.9900C13A—H13A0.9500
C5A—C6A1.519 (4)C14A—C15A1.375 (4)
C5A—H5A10.9900C14A—H14A0.9500
C5A—H5A20.9900C15A—C16A1.395 (4)
C6A—H6A10.9900C15A—H15A0.9500
C6A—H6A20.9900C16A—H16A0.9500
O1A—H1A10.8400C21A—C26A1.379 (4)
O2A—H2A10.8400C21A—C22A1.396 (4)
C1A'—O1A'1.438 (6)C22A—C23A1.386 (4)
C1A'—C6A'1.510 (7)C22A—H22A0.9500
C1A'—C2A'1.512 (6)C23A—C24A1.383 (4)
C1A'—H1A'1.0000C23A—H23A0.9500
C2A'—O2A'1.441 (6)C24A—C25A1.375 (4)
C2A'—C3A'1.526 (6)C24A—H24A0.9500
C2A'—H2A'1.0000C25A—C26A1.397 (4)
C3A'—C4A'1.534 (7)C25A—H25A0.9500
C3A'—H3A30.9900C26A—H26A0.9500
C3A'—H3A40.9900C31A—C36A1.386 (4)
C4A'—C5A'1.526 (6)C31A—C32A1.396 (4)
C4A'—H4A30.9900C32A—C33A1.387 (4)
C4A'—H4A40.9900C32A—H32A0.9500
C5A'—C6A'1.513 (6)C33A—C34A1.381 (4)
C5A'—H5A30.9900C33A—H33A0.9500
C5A'—H5A40.9900C34A—C35A1.386 (4)
C6A'—H6A30.9900C34A—H34A0.9500
C6A'—H6A40.9900C35A—C36A1.389 (4)
O1A'—H1A20.8400C35A—H35A0.9500
O2A'—H2A20.8400C36A—H36A0.9500
C1B—O1B1.438 (4)P01B—O11B1.4813 (19)
C1B—C2B1.502 (4)P01B—C21B1.797 (3)
C1B—C6B1.520 (4)P01B—C11B1.808 (3)
C1B—H1B1.0000P01B—C31B1.809 (3)
C2B—O2B1.434 (4)C11B—C12B1.393 (4)
C2B—C3B1.520 (4)C11B—C16B1.393 (4)
C2B—H2B1.0000C12B—C13B1.393 (4)
C3B—C4B1.528 (4)C12B—H12B0.9500
C3B—H3B10.9900C13B—C14B1.372 (4)
C3B—H3B20.9900C13B—H13B0.9500
C4B—C5B1.521 (4)C14B—C15B1.385 (4)
C4B—H4B10.9900C14B—H14B0.9500
C4B—H4B20.9900C15B—C16B1.390 (4)
C5B—C6B1.509 (4)C15B—H15B0.9500
C5B—H5B10.9900C16B—H16B0.9500
C5B—H5B20.9900C21B—C26B1.379 (4)
C6B—H6B10.9900C21B—C22B1.394 (4)
C6B—H6B20.9900C22B—C23B1.390 (4)
O1B—H1B10.8400C22B—H22B0.9500
O2B—H2B10.8400C23B—C24B1.379 (4)
C1B'—O1B'1.436 (7)C23B—H23B0.9500
C1B'—C2B'1.506 (6)C24B—C25B1.377 (4)
C1B'—C6B'1.520 (7)C24B—H24B0.9500
C1B'—H1B'1.0000C25B—C26B1.392 (4)
C2B'—O2B'1.435 (7)C25B—H25B0.9500
C2B'—C3B'1.521 (6)C26B—H26B0.9500
C2B'—H2B'1.0000C31B—C32B1.384 (4)
C3B'—C4B'1.527 (7)C31B—C36B1.389 (4)
C3B'—H3B30.9900C32B—C33B1.392 (4)
C3B'—H3B40.9900C32B—H32B0.9500
C4B'—C5B'1.519 (6)C33B—C34B1.375 (4)
C4B'—H4B30.9900C33B—H33B0.9500
C4B'—H4B40.9900C34B—C35B1.379 (4)
C5B'—C6B'1.506 (6)C34B—H34B0.9500
C5B'—H5B30.9900C35B—C36B1.390 (4)
C5B'—H5B40.9900C35B—H35B0.9500
C6B'—H6B30.9900C36B—H36B0.9500
O1A—C1A—C6A112.2 (3)C6B'—C5B'—C4B'111.5 (8)
O1A—C1A—C2A107.4 (3)C6B'—C5B'—H5B3109.3
C6A—C1A—C2A111.2 (3)C4B'—C5B'—H5B3109.3
O1A—C1A—H1A108.6C6B'—C5B'—H5B4109.3
C6A—C1A—H1A108.6C4B'—C5B'—H5B4109.3
C2A—C1A—H1A108.6H5B3—C5B'—H5B4108.0
O2A—C2A—C1A110.9 (3)C5B'—C6B'—C1B'111.3 (8)
O2A—C2A—C3A108.3 (3)C5B'—C6B'—H6B3109.4
C1A—C2A—C3A110.5 (3)C1B'—C6B'—H6B3109.4
O2A—C2A—H2A109.0C5B'—C6B'—H6B4109.4
C1A—C2A—H2A109.0C1B'—C6B'—H6B4109.4
C3A—C2A—H2A109.0H6B3—C6B'—H6B4108.0
C2A—C3A—C4A110.7 (3)C1B'—O1B'—H1B2109.5
C2A—C3A—H3A1109.5C2B'—O2B'—H2B2109.5
C4A—C3A—H3A1109.5O11A—P01A—C21A114.17 (12)
C2A—C3A—H3A2109.5O11A—P01A—C31A111.69 (12)
C4A—C3A—H3A2109.5C21A—P01A—C31A106.27 (13)
H3A1—C3A—H3A2108.1O11A—P01A—C11A111.84 (12)
C5A—C4A—C3A111.2 (3)C21A—P01A—C11A105.95 (12)
C5A—C4A—H4A1109.4C31A—P01A—C11A106.40 (12)
C3A—C4A—H4A1109.4C16A—C11A—C12A119.6 (3)
C5A—C4A—H4A2109.4C16A—C11A—P01A123.2 (2)
C3A—C4A—H4A2109.4C12A—C11A—P01A117.2 (2)
H4A1—C4A—H4A2108.0C13A—C12A—C11A120.2 (3)
C6A—C5A—C4A110.0 (3)C13A—C12A—H12A119.9
C6A—C5A—H5A1109.7C11A—C12A—H12A119.9
C4A—C5A—H5A1109.7C12A—C13A—C14A120.2 (3)
C6A—C5A—H5A2109.7C12A—C13A—H13A119.9
C4A—C5A—H5A2109.7C14A—C13A—H13A119.9
H5A1—C5A—H5A2108.2C15A—C14A—C13A120.0 (3)
C1A—C6A—C5A111.4 (4)C15A—C14A—H14A120.0
C1A—C6A—H6A1109.4C13A—C14A—H14A120.0
C5A—C6A—H6A1109.4C14A—C15A—C16A120.9 (3)
C1A—C6A—H6A2109.4C14A—C15A—H15A119.6
C5A—C6A—H6A2109.4C16A—C15A—H15A119.6
H6A1—C6A—H6A2108.0C15A—C16A—C11A119.1 (3)
O1A'—C1A'—C6A'111.0 (8)C15A—C16A—H16A120.4
O1A'—C1A'—C2A'107.9 (7)C11A—C16A—H16A120.4
C6A'—C1A'—C2A'111.5 (8)C26A—C21A—C22A118.5 (3)
O1A'—C1A'—H1A'108.8C26A—C21A—P01A123.3 (2)
C6A'—C1A'—H1A'108.8C22A—C21A—P01A118.1 (2)
C2A'—C1A'—H1A'108.8C23A—C22A—C21A120.5 (3)
O2A'—C2A'—C1A'111.1 (8)C23A—C22A—H22A119.8
O2A'—C2A'—C3A'107.7 (7)C21A—C22A—H22A119.8
C1A'—C2A'—C3A'110.0 (7)C24A—C23A—C22A120.2 (3)
O2A'—C2A'—H2A'109.3C24A—C23A—H23A119.9
C1A'—C2A'—H2A'109.3C22A—C23A—H23A119.9
C3A'—C2A'—H2A'109.3C25A—C24A—C23A120.0 (3)
C2A'—C3A'—C4A'109.8 (7)C25A—C24A—H24A120.0
C2A'—C3A'—H3A3109.7C23A—C24A—H24A120.0
C4A'—C3A'—H3A3109.7C24A—C25A—C26A119.7 (3)
C2A'—C3A'—H3A4109.7C24A—C25A—H25A120.2
C4A'—C3A'—H3A4109.7C26A—C25A—H25A120.2
H3A3—C3A'—H3A4108.2C21A—C26A—C25A121.1 (3)
C5A'—C4A'—C3A'109.8 (7)C21A—C26A—H26A119.5
C5A'—C4A'—H4A3109.7C25A—C26A—H26A119.5
C3A'—C4A'—H4A3109.7C36A—C31A—C32A118.8 (3)
C5A'—C4A'—H4A4109.7C36A—C31A—P01A123.3 (2)
C3A'—C4A'—H4A4109.7C32A—C31A—P01A117.9 (2)
H4A3—C4A'—H4A4108.2C33A—C32A—C31A120.5 (3)
C6A'—C5A'—C4A'110.2 (7)C33A—C32A—H32A119.7
C6A'—C5A'—H5A3109.6C31A—C32A—H32A119.7
C4A'—C5A'—H5A3109.6C34A—C33A—C32A120.1 (3)
C6A'—C5A'—H5A4109.6C34A—C33A—H33A120.0
C4A'—C5A'—H5A4109.6C32A—C33A—H33A120.0
H5A3—C5A'—H5A4108.1C33A—C34A—C35A119.9 (3)
C1A'—C6A'—C5A'111.5 (8)C33A—C34A—H34A120.1
C1A'—C6A'—H6A3109.3C35A—C34A—H34A120.1
C5A'—C6A'—H6A3109.3C34A—C35A—C36A120.1 (3)
C1A'—C6A'—H6A4109.3C34A—C35A—H35A120.0
C5A'—C6A'—H6A4109.3C36A—C35A—H35A120.0
H6A3—C6A'—H6A4108.0C31A—C36A—C35A120.6 (3)
C1A'—O1A'—H1A2109.5C31A—C36A—H36A119.7
C2A'—O2A'—H2A2109.5C35A—C36A—H36A119.7
O1B—C1B—C2B111.3 (3)O11B—P01B—C21B114.03 (12)
O1B—C1B—C6B108.1 (3)O11B—P01B—C11B111.53 (12)
C2B—C1B—C6B111.5 (3)C21B—P01B—C11B105.89 (12)
O1B—C1B—H1B108.6O11B—P01B—C31B111.69 (12)
C2B—C1B—H1B108.6C21B—P01B—C31B106.33 (13)
C6B—C1B—H1B108.6C11B—P01B—C31B106.90 (12)
O2B—C2B—C1B107.8 (3)C12B—C11B—C16B119.9 (3)
O2B—C2B—C3B111.9 (3)C12B—C11B—P01B117.1 (2)
C1B—C2B—C3B110.6 (3)C16B—C11B—P01B123.0 (2)
O2B—C2B—H2B108.8C13B—C12B—C11B119.9 (3)
C1B—C2B—H2B108.8C13B—C12B—H12B120.0
C3B—C2B—H2B108.8C11B—C12B—H12B120.0
C2B—C3B—C4B110.6 (3)C14B—C13B—C12B120.2 (3)
C2B—C3B—H3B1109.5C14B—C13B—H13B119.9
C4B—C3B—H3B1109.5C12B—C13B—H13B119.9
C2B—C3B—H3B2109.5C13B—C14B—C15B120.0 (3)
C4B—C3B—H3B2109.5C13B—C14B—H14B120.0
H3B1—C3B—H3B2108.1C15B—C14B—H14B120.0
C5B—C4B—C3B111.0 (3)C14B—C15B—C16B120.8 (3)
C5B—C4B—H4B1109.4C14B—C15B—H15B119.6
C3B—C4B—H4B1109.4C16B—C15B—H15B119.6
C5B—C4B—H4B2109.4C15B—C16B—C11B119.1 (3)
C3B—C4B—H4B2109.4C15B—C16B—H16B120.4
H4B1—C4B—H4B2108.0C11B—C16B—H16B120.4
C6B—C5B—C4B111.6 (3)C26B—C21B—C22B118.7 (3)
C6B—C5B—H5B1109.3C26B—C21B—P01B123.2 (2)
C4B—C5B—H5B1109.3C22B—C21B—P01B118.0 (2)
C6B—C5B—H5B2109.3C23B—C22B—C21B120.1 (3)
C4B—C5B—H5B2109.3C23B—C22B—H22B119.9
H5B1—C5B—H5B2108.0C21B—C22B—H22B119.9
C5B—C6B—C1B111.4 (3)C24B—C23B—C22B120.6 (3)
C5B—C6B—H6B1109.3C24B—C23B—H23B119.7
C1B—C6B—H6B1109.3C22B—C23B—H23B119.7
C5B—C6B—H6B2109.3C25B—C24B—C23B119.5 (3)
C1B—C6B—H6B2109.3C25B—C24B—H24B120.2
H6B1—C6B—H6B2108.0C23B—C24B—H24B120.2
O1B'—C1B'—C2B'111.2 (9)C24B—C25B—C26B120.0 (3)
O1B'—C1B'—C6B'108.7 (9)C24B—C25B—H25B120.0
C2B'—C1B'—C6B'111.0 (8)C26B—C25B—H25B120.0
O1B'—C1B'—H1B'108.6C21B—C26B—C25B121.1 (3)
C2B'—C1B'—H1B'108.6C21B—C26B—H26B119.5
C6B'—C1B'—H1B'108.6C25B—C26B—H26B119.5
O2B'—C2B'—C1B'107.5 (9)C32B—C31B—C36B119.0 (3)
O2B'—C2B'—C3B'111.7 (9)C32B—C31B—P01B118.0 (2)
C1B'—C2B'—C3B'110.7 (8)C36B—C31B—P01B123.1 (2)
O2B'—C2B'—H2B'109.0C31B—C32B—C33B120.7 (3)
C1B'—C2B'—H2B'109.0C31B—C32B—H32B119.7
C3B'—C2B'—H2B'109.0C33B—C32B—H32B119.7
C2B'—C3B'—C4B'110.8 (8)C34B—C33B—C32B119.8 (3)
C2B'—C3B'—H3B3109.5C34B—C33B—H33B120.1
C4B'—C3B'—H3B3109.5C32B—C33B—H33B120.1
C2B'—C3B'—H3B4109.5C33B—C34B—C35B120.2 (3)
C4B'—C3B'—H3B4109.5C33B—C34B—H34B119.9
H3B3—C3B'—H3B4108.1C35B—C34B—H34B119.9
C5B'—C4B'—C3B'111.3 (9)C34B—C35B—C36B120.0 (3)
C5B'—C4B'—H4B3109.4C34B—C35B—H35B120.0
C3B'—C4B'—H4B3109.4C36B—C35B—H35B120.0
C5B'—C4B'—H4B4109.4C31B—C36B—C35B120.3 (3)
C3B'—C4B'—H4B4109.4C31B—C36B—H36B119.8
H4B3—C4B'—H4B4108.0C35B—C36B—H36B119.8
O1A—C1A—C2A—O2A59.7 (5)C26A—C21A—C22A—C23A1.0 (4)
C6A—C1A—C2A—O2A177.2 (3)P01A—C21A—C22A—C23A176.0 (2)
O1A—C1A—C2A—C3A179.8 (3)C21A—C22A—C23A—C24A0.2 (5)
C6A—C1A—C2A—C3A57.1 (6)C22A—C23A—C24A—C25A1.5 (5)
O2A—C2A—C3A—C4A177.9 (3)C23A—C24A—C25A—C26A1.5 (5)
C1A—C2A—C3A—C4A56.3 (6)C22A—C21A—C26A—C25A1.1 (4)
C2A—C3A—C4A—C5A56.1 (6)P01A—C21A—C26A—C25A175.9 (2)
C3A—C4A—C5A—C6A55.6 (6)C24A—C25A—C26A—C21A0.2 (4)
O1A—C1A—C6A—C5A177.9 (3)O11A—P01A—C31A—C36A158.6 (2)
C2A—C1A—C6A—C5A57.6 (7)C21A—P01A—C31A—C36A76.3 (3)
C4A—C5A—C6A—C1A56.3 (7)C11A—P01A—C31A—C36A36.3 (3)
O1A'—C1A'—C2A'—O2A'61.9 (13)O11A—P01A—C31A—C32A20.0 (3)
C6A'—C1A'—C2A'—O2A'176.0 (13)C21A—P01A—C31A—C32A105.1 (2)
O1A'—C1A'—C2A'—C3A'178.9 (11)C11A—P01A—C31A—C32A142.3 (2)
C6A'—C1A'—C2A'—C3A'56.8 (14)C36A—C31A—C32A—C33A1.3 (4)
O2A'—C2A'—C3A'—C4A'179.5 (13)P01A—C31A—C32A—C33A177.3 (2)
C1A'—C2A'—C3A'—C4A'58.3 (13)C31A—C32A—C33A—C34A1.1 (4)
C2A'—C3A'—C4A'—C5A'59.1 (16)C32A—C33A—C34A—C35A0.3 (4)
C3A'—C4A'—C5A'—C6A'57.8 (15)C33A—C34A—C35A—C36A1.5 (4)
O1A'—C1A'—C6A'—C5A'176.5 (14)C32A—C31A—C36A—C35A0.2 (4)
C2A'—C1A'—C6A'—C5A'56.2 (19)P01A—C31A—C36A—C35A178.4 (2)
C4A'—C5A'—C6A'—C1A'56.4 (17)C34A—C35A—C36A—C31A1.2 (4)
O1B—C1B—C2B—O2B59.5 (5)O11B—P01B—C11B—C12B22.6 (2)
C6B—C1B—C2B—O2B179.8 (3)C21B—P01B—C11B—C12B147.1 (2)
O1B—C1B—C2B—C3B177.8 (2)C31B—P01B—C11B—C12B99.8 (2)
C6B—C1B—C2B—C3B57.1 (5)O11B—P01B—C11B—C16B158.8 (2)
O2B—C2B—C3B—C4B177.5 (3)C21B—P01B—C11B—C16B34.2 (3)
C1B—C2B—C3B—C4B57.2 (6)C31B—P01B—C11B—C16B78.9 (2)
C2B—C3B—C4B—C5B55.8 (6)C16B—C11B—C12B—C13B0.2 (4)
C3B—C4B—C5B—C6B54.4 (7)P01B—C11B—C12B—C13B178.5 (2)
C4B—C5B—C6B—C1B54.0 (6)C11B—C12B—C13B—C14B1.4 (4)
O1B—C1B—C6B—C5B178.2 (3)C12B—C13B—C14B—C15B1.9 (4)
C2B—C1B—C6B—C5B55.5 (6)C13B—C14B—C15B—C16B0.9 (4)
O1B'—C1B'—C2B'—O2B'59.3 (18)C14B—C15B—C16B—C11B0.7 (4)
C6B'—C1B'—C2B'—O2B'179.6 (17)C12B—C11B—C16B—C15B1.2 (4)
O1B'—C1B'—C2B'—C3B'178.5 (14)P01B—C11B—C16B—C15B177.4 (2)
C6B'—C1B'—C2B'—C3B'57.4 (15)O11B—P01B—C21B—C26B113.4 (2)
O2B'—C2B'—C3B'—C4B'176.3 (18)C11B—P01B—C21B—C26B123.6 (2)
C1B'—C2B'—C3B'—C4B'56.5 (17)C31B—P01B—C21B—C26B10.1 (3)
C2B'—C3B'—C4B'—C5B'55 (2)O11B—P01B—C21B—C22B63.1 (2)
C3B'—C4B'—C5B'—C6B'54 (2)C11B—P01B—C21B—C22B59.9 (2)
C4B'—C5B'—C6B'—C1B'55.1 (18)C31B—P01B—C21B—C22B173.4 (2)
O1B'—C1B'—C6B'—C5B'179.4 (17)C26B—C21B—C22B—C23B0.7 (4)
C2B'—C1B'—C6B'—C5B'57 (2)P01B—C21B—C22B—C23B176.0 (2)
O11A—P01A—C11A—C16A158.4 (2)C21B—C22B—C23B—C24B0.2 (5)
C21A—P01A—C11A—C16A33.4 (3)C22B—C23B—C24B—C25B0.6 (4)
C31A—P01A—C11A—C16A79.4 (2)C23B—C24B—C25B—C26B0.8 (4)
O11A—P01A—C11A—C12A22.9 (2)C22B—C21B—C26B—C25B0.5 (4)
C21A—P01A—C11A—C12A147.9 (2)P01B—C21B—C26B—C25B176.1 (2)
C31A—P01A—C11A—C12A99.3 (2)C24B—C25B—C26B—C21B0.3 (4)
C16A—C11A—C12A—C13A1.1 (4)O11B—P01B—C31B—C32B22.1 (2)
P01A—C11A—C12A—C13A177.7 (2)C21B—P01B—C31B—C32B102.8 (2)
C11A—C12A—C13A—C14A0.2 (4)C11B—P01B—C31B—C32B144.4 (2)
C12A—C13A—C14A—C15A0.8 (4)O11B—P01B—C31B—C36B158.2 (2)
C13A—C14A—C15A—C16A0.1 (4)C21B—P01B—C31B—C36B76.8 (3)
C14A—C15A—C16A—C11A1.2 (4)C11B—P01B—C31B—C36B35.9 (3)
C12A—C11A—C16A—C15A1.7 (4)C36B—C31B—C32B—C33B1.8 (4)
P01A—C11A—C16A—C15A176.96 (19)P01B—C31B—C32B—C33B178.5 (2)
O11A—P01A—C21A—C26A114.5 (2)C31B—C32B—C33B—C34B1.1 (4)
C31A—P01A—C21A—C26A9.0 (3)C32B—C33B—C34B—C35B0.3 (4)
C11A—P01A—C21A—C26A121.9 (2)C33B—C34B—C35B—C36B1.0 (4)
O11A—P01A—C21A—C22A62.4 (2)C32B—C31B—C36B—C35B1.1 (4)
C31A—P01A—C21A—C22A174.0 (2)P01B—C31B—C36B—C35B179.2 (2)
C11A—P01A—C21A—C22A61.1 (2)C34B—C35B—C36B—C31B0.3 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A1···O1Bi0.841.912.732 (5)165
O2A—H2A1···O1Aii0.841.912.708 (5)159
O1B—H1B1···O2Bi0.841.982.765 (4)155
O2B—H2B1···O2Aii0.841.922.752 (5)171
O1A—H1A2···O2Aii0.842.102.77 (2)136
O2A—H2A2···O2Bii0.841.772.58 (3)162
O1B—H1B2···O1Ai0.842.022.84 (3)169
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.
(ethanol90Ktri) 1:1 rac-1,2-cyclohexanediol triphenylphosphine oxide top
Crystal data top
C6H12O2·C18H15OPZ = 4
Mr = 394.43F(000) = 840
Triclinic, P1Dx = 1.270 Mg m3
a = 9.273 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.919 (1) ÅCell parameters from 9409 reflections
c = 21.262 (2) Åθ = 1.0–27.5°
α = 100.66 (1)°µ = 0.16 mm1
β = 102.56 (1)°T = 90 K
γ = 90.23 (1)°Lath, colorless
V = 2062.8 (4) Å30.25 × 0.20 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer
7244 independent reflections
Radiation source: fine-focus sealed tube4413 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.065
Detector resolution: 10 pixels mm-1θmax = 25.0°, θmin = 1.0°
1.0° ω scans at fixed χ = 55°h = 1111
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
k = 1212
Tmin = 0.96, Tmax = 0.98l = 2525
14485 measured 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.0514P)2]
where P = (Fo2 + 2Fc2)/3
7244 reflections(Δ/σ)max = 0.001
564 parametersΔρmax = 0.30 e Å3
148 restraintsΔρmin = 0.29 e Å3
Crystal data top
C6H12O2·C18H15OPγ = 90.23 (1)°
Mr = 394.43V = 2062.8 (4) Å3
Triclinic, P1Z = 4
a = 9.273 (1) ÅMo Kα radiation
b = 10.919 (1) ŵ = 0.16 mm1
c = 21.262 (2) ÅT = 90 K
α = 100.66 (1)°0.25 × 0.20 × 0.12 mm
β = 102.56 (1)°
Data collection top
Nonius KappaCCD
diffractometer
7244 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
4413 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.98Rint = 0.065
14485 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049148 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.00Δρmax = 0.30 e Å3
7244 reflectionsΔρmin = 0.29 e Å3
564 parameters
Special details top

Experimental. The crystal-to-detector distance was 45 mm. Each frame was measured for 15 s. The number of scan sets measured was 9 the total number of frames measured was 1008.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.7769 (5)0.0755 (4)0.0373 (3)0.0260 (15)0.700 (5)
H1A0.82910.05670.00030.031*0.700 (5)
C2A0.7472 (5)0.0451 (4)0.0582 (3)0.0234 (15)0.700 (5)
H2A0.69150.02780.09400.028*0.700 (5)
C3A0.8917 (5)0.1042 (5)0.0834 (3)0.0288 (15)0.700 (5)
H3A10.94410.12720.04730.035*0.700 (5)
H3A20.87040.18120.09870.035*0.700 (5)
C4A0.9903 (7)0.0126 (5)0.1401 (4)0.0310 (18)0.700 (5)
H4A10.94170.00400.17770.037*0.700 (5)
H4A21.08570.05060.15460.037*0.700 (5)
C5A1.0190 (5)0.1097 (5)0.1193 (3)0.0305 (13)0.700 (5)
H5A11.07730.16900.15740.037*0.700 (5)
H5A21.07730.09470.08500.037*0.700 (5)
C6A0.8744 (7)0.1656 (5)0.0931 (4)0.0281 (17)0.700 (5)
H6A10.82140.18880.12900.034*0.700 (5)
H6A20.89500.24250.07760.034*0.700 (5)
O1A0.6375 (4)0.1265 (5)0.0137 (2)0.0261 (11)0.700 (5)
H1A10.65180.19890.00750.039*0.700 (5)
O2A0.6604 (6)0.1319 (5)0.0035 (3)0.0312 (16)0.700 (5)
H2A10.57080.11490.00140.047*0.700 (5)
C1A'0.7470 (12)0.0894 (9)0.0542 (5)0.0260 (15)0.300 (5)
H1A'0.68260.10560.08670.031*0.300 (5)
C2A'0.7722 (12)0.0483 (9)0.0406 (6)0.0234 (15)0.300 (5)
H2A'0.83110.06550.00590.028*0.300 (5)
C3A'0.8576 (13)0.0897 (10)0.1022 (6)0.0288 (15)0.300 (5)
H3A30.87560.17980.09210.035*0.300 (5)
H3A40.79890.07630.13640.035*0.300 (5)
C4A'1.0063 (15)0.0144 (11)0.1276 (10)0.0310 (18)0.300 (5)
H4A31.06190.04110.16780.037*0.300 (5)
H4A41.06650.03000.09400.037*0.300 (5)
C5A'0.9780 (13)0.1244 (11)0.1430 (5)0.0305 (13)0.300 (5)
H5A30.92220.14040.17820.037*0.300 (5)
H5A41.07350.17300.15870.037*0.300 (5)
C6A'0.8910 (19)0.1656 (11)0.0825 (10)0.0281 (17)0.300 (5)
H6A30.95130.15720.04890.034*0.300 (5)
H6A40.86950.25480.09370.034*0.300 (5)
O1A'0.6718 (11)0.1260 (12)0.0055 (5)0.0261 (11)0.300 (5)
H1A20.59100.08470.02020.039*0.300 (5)
O2A'0.6335 (14)0.1192 (13)0.0173 (8)0.0312 (16)0.300 (5)
H2A20.64830.19530.01640.047*0.300 (5)
C1B0.3076 (6)0.5896 (4)0.0522 (2)0.0233 (13)0.759 (6)
H1B0.40430.60690.08480.028*0.759 (6)
C2B0.2694 (6)0.4522 (4)0.0404 (3)0.0258 (14)0.759 (6)
H2B0.17430.43400.00680.031*0.759 (6)
C3B0.2485 (6)0.4125 (5)0.1027 (3)0.0328 (15)0.759 (6)
H3B10.34320.42500.13580.039*0.759 (6)
H3B20.21840.32270.09310.039*0.759 (6)
C4B0.1306 (11)0.4882 (5)0.1302 (4)0.0377 (15)0.759 (6)
H4B10.03340.46730.09940.045*0.759 (6)
H4B20.12380.46550.17250.045*0.759 (6)
C5B0.1653 (6)0.6271 (5)0.1408 (2)0.0327 (13)0.759 (6)
H5B10.08150.67270.15420.039*0.759 (6)
H5B20.25380.65000.17700.039*0.759 (6)
C6B0.1930 (8)0.6664 (5)0.0801 (3)0.0272 (16)0.759 (6)
H6B10.22670.75540.09090.033*0.759 (6)
H6B20.09920.65760.04650.033*0.759 (6)
O1B0.3239 (5)0.6272 (5)0.0071 (2)0.0315 (12)0.759 (6)
H1B10.40470.60330.01580.047*0.759 (6)
O2B0.3828 (10)0.3853 (5)0.0147 (4)0.035 (2)0.759 (6)
H2B10.35920.30860.00530.053*0.759 (6)
C1B'0.2625 (16)0.5741 (12)0.0376 (7)0.0233 (13)0.241 (6)
H1B'0.17340.55380.00060.028*0.241 (6)
C2B'0.3127 (16)0.4547 (12)0.0594 (7)0.0258 (14)0.241 (6)
H2B'0.40260.47520.09590.031*0.241 (6)
C3B'0.1952 (19)0.3955 (12)0.0853 (9)0.0328 (15)0.241 (6)
H3B30.23470.32140.10270.039*0.241 (6)
H3B40.10860.36720.04880.039*0.241 (6)
C4B'0.146 (3)0.4866 (17)0.1393 (12)0.0377 (15)0.241 (6)
H4B30.06220.44790.15160.045*0.241 (6)
H4B40.22860.50400.17860.045*0.241 (6)
C5B'0.1001 (16)0.6081 (15)0.1178 (8)0.0327 (13)0.241 (6)
H5B30.00860.59250.08280.039*0.241 (6)
H5B40.07830.66750.15540.039*0.241 (6)
C6B'0.220 (3)0.6647 (12)0.0927 (11)0.0272 (16)0.241 (6)
H6B30.30780.68860.12900.033*0.241 (6)
H6B40.18430.74120.07670.033*0.241 (6)
O1B'0.3760 (15)0.6294 (15)0.0141 (7)0.0315 (12)0.241 (6)
H1B20.35480.70260.00990.047*0.241 (6)
O2B'0.354 (4)0.3729 (18)0.0061 (15)0.035 (2)0.241 (6)
H2B20.29180.37580.02890.053*0.241 (6)
P01A0.78802 (10)0.16277 (9)0.33636 (4)0.0212 (2)
O11A0.8443 (2)0.2930 (2)0.34173 (10)0.0237 (6)
C11A0.6319 (4)0.1191 (3)0.26769 (15)0.0203 (8)
C12A0.6176 (4)0.1855 (3)0.21659 (16)0.0233 (9)
H12A0.68580.25280.21980.028*
C13A0.5041 (4)0.1533 (4)0.16137 (17)0.0313 (10)
H13A0.49500.19810.12650.038*
C14A0.4044 (4)0.0567 (4)0.15678 (18)0.0336 (10)
H14A0.32670.03500.11880.040*
C15A0.4171 (4)0.0089 (3)0.20729 (17)0.0277 (9)
H15A0.34850.07610.20350.033*
C16A0.5295 (3)0.0225 (3)0.26368 (16)0.0229 (9)
H16A0.53630.02120.29880.027*
C21A0.7267 (4)0.1354 (3)0.40729 (16)0.0211 (8)
C22A0.6075 (4)0.2019 (3)0.42426 (17)0.0289 (9)
H22A0.55750.25510.39690.035*
C23A0.5627 (4)0.1901 (4)0.48066 (18)0.0362 (10)
H23A0.48230.23620.49200.043*
C24A0.6323 (4)0.1128 (3)0.52070 (17)0.0311 (10)
H24A0.60070.10590.55960.037*
C25A0.7479 (4)0.0456 (4)0.50419 (17)0.0336 (10)
H25A0.79610.00860.53140.040*
C26A0.7945 (4)0.0571 (3)0.44738 (16)0.0283 (9)
H26A0.87430.01010.43620.034*
C31A0.9267 (4)0.0523 (3)0.32395 (16)0.0227 (9)
C32A1.0744 (4)0.0945 (3)0.34126 (16)0.0240 (9)
H32A1.09940.17970.36060.029*
C33A1.1856 (4)0.0139 (3)0.33069 (16)0.0269 (9)
H33A1.28590.04420.34240.032*
C34A1.1507 (4)0.1104 (3)0.30317 (16)0.0282 (9)
H34A1.22670.16520.29520.034*
C35A1.0050 (4)0.1548 (3)0.28724 (16)0.0271 (9)
H35A0.98090.24080.26960.033*
C36A0.8939 (4)0.0731 (3)0.29711 (16)0.0250 (9)
H36A0.79370.10360.28530.030*
P01B0.54979 (10)0.66149 (9)0.33493 (4)0.0211 (2)
O11B0.4992 (2)0.7910 (2)0.34083 (10)0.0244 (6)
C11B0.6386 (3)0.6195 (3)0.26699 (15)0.0185 (8)
C12B0.6048 (4)0.6880 (3)0.21681 (15)0.0221 (9)
H12B0.53930.75440.21990.026*
C13B0.6668 (4)0.6591 (4)0.16222 (17)0.0302 (9)
H13B0.64470.70680.12850.036*
C14B0.7597 (4)0.5621 (4)0.15678 (18)0.0328 (10)
H14B0.79970.54120.11890.039*
C15B0.7950 (4)0.4948 (3)0.20664 (17)0.0276 (9)
H15B0.85990.42820.20290.033*
C16B0.7361 (3)0.5239 (3)0.26236 (16)0.0231 (9)
H16B0.76270.47850.29690.028*
C21B0.6805 (4)0.6338 (3)0.40610 (15)0.0197 (8)
C22B0.8169 (4)0.7003 (3)0.42353 (17)0.0303 (10)
H22B0.83990.75420.39640.036*
C23B0.9192 (4)0.6880 (4)0.48033 (18)0.0369 (10)
H23B1.01210.73290.49170.044*
C24B0.8854 (4)0.6105 (4)0.52010 (17)0.0321 (10)
H24B0.95410.60360.55940.039*
C25B0.7523 (4)0.5433 (4)0.50277 (17)0.0328 (10)
H25B0.73010.48880.52980.039*
C26B0.6500 (4)0.5547 (3)0.44588 (16)0.0286 (9)
H26B0.55840.50780.43430.034*
C31B0.3969 (3)0.5490 (3)0.32146 (15)0.0195 (8)
C32B0.2682 (4)0.5905 (3)0.33963 (15)0.0216 (8)
H32B0.26370.67530.35960.026*
C33B0.1460 (4)0.5096 (4)0.32904 (16)0.0286 (9)
H33B0.05810.53900.34150.034*
C34B0.1523 (4)0.3865 (4)0.30039 (16)0.0288 (9)
H34B0.06820.33130.29250.035*
C35B0.2811 (4)0.3429 (3)0.28298 (17)0.0294 (9)
H35B0.28580.25750.26420.035*
C36B0.4032 (4)0.4240 (3)0.29301 (16)0.0264 (9)
H36B0.49090.39430.28050.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.021 (3)0.030 (2)0.026 (3)0.0064 (18)0.005 (2)0.005 (2)
C2A0.020 (2)0.0266 (19)0.023 (3)0.0015 (17)0.003 (2)0.005 (2)
C3A0.022 (3)0.033 (2)0.034 (3)0.0058 (19)0.007 (2)0.010 (2)
C4A0.025 (2)0.047 (2)0.021 (4)0.0029 (18)0.001 (2)0.012 (2)
C5A0.026 (3)0.040 (2)0.023 (3)0.001 (2)0.004 (2)0.002 (2)
C6A0.023 (2)0.027 (2)0.034 (3)0.0015 (16)0.008 (2)0.0014 (19)
O1A0.019 (2)0.0271 (17)0.035 (3)0.0024 (16)0.0069 (16)0.009 (2)
O2A0.025 (2)0.032 (2)0.034 (3)0.0031 (18)0.003 (2)0.0018 (19)
C1A'0.021 (3)0.030 (2)0.026 (3)0.0064 (18)0.005 (2)0.005 (2)
C2A'0.020 (2)0.0266 (19)0.023 (3)0.0015 (17)0.003 (2)0.005 (2)
C3A'0.022 (3)0.033 (2)0.034 (3)0.0058 (19)0.007 (2)0.010 (2)
C4A'0.025 (2)0.047 (2)0.021 (4)0.0029 (18)0.001 (2)0.012 (2)
C5A'0.026 (3)0.040 (2)0.023 (3)0.001 (2)0.004 (2)0.002 (2)
C6A'0.023 (2)0.027 (2)0.034 (3)0.0015 (16)0.008 (2)0.0014 (19)
O1A'0.019 (2)0.0271 (17)0.035 (3)0.0024 (16)0.0069 (16)0.009 (2)
O2A'0.025 (2)0.032 (2)0.034 (3)0.0031 (18)0.003 (2)0.0018 (19)
C1B0.023 (3)0.026 (2)0.019 (3)0.005 (2)0.004 (3)0.0009 (19)
C2B0.027 (3)0.0266 (19)0.027 (3)0.007 (2)0.012 (3)0.006 (2)
C3B0.035 (4)0.035 (2)0.034 (3)0.007 (2)0.015 (3)0.013 (2)
C4B0.042 (3)0.047 (2)0.034 (3)0.012 (2)0.023 (3)0.017 (2)
C5B0.035 (4)0.041 (2)0.024 (3)0.009 (3)0.012 (3)0.005 (2)
C6B0.026 (3)0.026 (2)0.029 (3)0.0033 (19)0.008 (3)0.0021 (19)
O1B0.035 (3)0.0321 (18)0.031 (3)0.004 (2)0.016 (2)0.006 (2)
O2B0.041 (5)0.031 (2)0.039 (3)0.013 (2)0.020 (3)0.0071 (19)
C1B'0.023 (3)0.026 (2)0.019 (3)0.005 (2)0.004 (3)0.0009 (19)
C2B'0.027 (3)0.0266 (19)0.027 (3)0.007 (2)0.012 (3)0.006 (2)
C3B'0.035 (4)0.035 (2)0.034 (3)0.007 (2)0.015 (3)0.013 (2)
C4B'0.042 (3)0.047 (2)0.034 (3)0.012 (2)0.023 (3)0.017 (2)
C5B'0.035 (4)0.041 (2)0.024 (3)0.009 (3)0.012 (3)0.005 (2)
C6B'0.026 (3)0.026 (2)0.029 (3)0.0033 (19)0.008 (3)0.0021 (19)
O1B'0.035 (3)0.0321 (18)0.031 (3)0.004 (2)0.016 (2)0.006 (2)
O2B'0.041 (5)0.031 (2)0.039 (3)0.013 (2)0.020 (3)0.0071 (19)
P01A0.0185 (5)0.0252 (6)0.0198 (6)0.0015 (4)0.0040 (4)0.0042 (4)
O11A0.0238 (14)0.0213 (15)0.0253 (14)0.0022 (11)0.0040 (11)0.0046 (11)
C11A0.018 (2)0.026 (2)0.015 (2)0.0053 (16)0.0038 (16)0.0001 (17)
C12A0.023 (2)0.025 (2)0.022 (2)0.0029 (17)0.0070 (17)0.0045 (18)
C13A0.034 (2)0.042 (3)0.020 (2)0.008 (2)0.0065 (19)0.0107 (19)
C14A0.023 (2)0.052 (3)0.022 (2)0.002 (2)0.0002 (18)0.003 (2)
C15A0.019 (2)0.031 (2)0.031 (2)0.0032 (17)0.0051 (18)0.0027 (19)
C16A0.020 (2)0.027 (2)0.023 (2)0.0029 (17)0.0084 (17)0.0030 (17)
C21A0.020 (2)0.021 (2)0.020 (2)0.0030 (17)0.0006 (16)0.0010 (17)
C22A0.033 (2)0.031 (2)0.022 (2)0.0073 (19)0.0073 (18)0.0042 (18)
C23A0.043 (3)0.038 (3)0.033 (2)0.008 (2)0.020 (2)0.003 (2)
C24A0.042 (3)0.035 (3)0.017 (2)0.010 (2)0.0143 (19)0.0023 (19)
C25A0.039 (2)0.041 (3)0.024 (2)0.002 (2)0.007 (2)0.0142 (19)
C26A0.024 (2)0.037 (3)0.024 (2)0.0003 (18)0.0051 (18)0.0062 (19)
C31A0.022 (2)0.030 (2)0.017 (2)0.0006 (17)0.0040 (16)0.0053 (17)
C32A0.023 (2)0.029 (2)0.021 (2)0.0011 (18)0.0062 (17)0.0060 (17)
C33A0.019 (2)0.040 (3)0.023 (2)0.0006 (19)0.0047 (17)0.0106 (19)
C34A0.027 (2)0.037 (3)0.025 (2)0.0143 (19)0.0112 (18)0.0113 (19)
C35A0.030 (2)0.025 (2)0.027 (2)0.0078 (19)0.0071 (18)0.0058 (18)
C36A0.0164 (19)0.034 (2)0.025 (2)0.0025 (18)0.0050 (17)0.0049 (18)
P01B0.0195 (5)0.0239 (6)0.0196 (5)0.0001 (4)0.0043 (4)0.0034 (4)
O11B0.0249 (14)0.0229 (15)0.0274 (14)0.0036 (11)0.0097 (11)0.0049 (11)
C11B0.0130 (19)0.020 (2)0.020 (2)0.0031 (16)0.0004 (15)0.0028 (17)
C12B0.0157 (19)0.029 (2)0.019 (2)0.0001 (16)0.0005 (16)0.0046 (17)
C13B0.030 (2)0.042 (3)0.017 (2)0.003 (2)0.0017 (18)0.0064 (18)
C14B0.024 (2)0.053 (3)0.021 (2)0.004 (2)0.0080 (18)0.002 (2)
C15B0.023 (2)0.034 (2)0.024 (2)0.0035 (18)0.0102 (18)0.0048 (19)
C16B0.019 (2)0.023 (2)0.026 (2)0.0016 (17)0.0024 (17)0.0034 (17)
C21B0.022 (2)0.022 (2)0.014 (2)0.0041 (17)0.0048 (16)0.0005 (16)
C22B0.032 (2)0.032 (2)0.025 (2)0.0073 (19)0.0011 (19)0.0067 (19)
C23B0.031 (2)0.041 (3)0.032 (2)0.005 (2)0.004 (2)0.002 (2)
C24B0.033 (2)0.038 (3)0.020 (2)0.007 (2)0.0012 (18)0.0014 (19)
C25B0.032 (2)0.042 (3)0.025 (2)0.003 (2)0.0028 (19)0.0101 (19)
C26B0.022 (2)0.035 (2)0.027 (2)0.0006 (18)0.0032 (18)0.0068 (19)
C31B0.0173 (19)0.028 (2)0.0124 (19)0.0002 (16)0.0005 (15)0.0058 (16)
C32B0.024 (2)0.025 (2)0.016 (2)0.0016 (17)0.0038 (16)0.0065 (16)
C33B0.021 (2)0.045 (3)0.025 (2)0.0041 (19)0.0085 (17)0.015 (2)
C34B0.020 (2)0.041 (3)0.026 (2)0.0075 (19)0.0015 (17)0.013 (2)
C35B0.025 (2)0.032 (2)0.030 (2)0.0039 (19)0.0041 (18)0.0067 (19)
C36B0.022 (2)0.028 (2)0.030 (2)0.0007 (18)0.0077 (17)0.0052 (18)
Geometric parameters (Å, º) top
C1A—O1A1.435 (5)C6B'—H6B40.9900
C1A—C2A1.509 (5)O1B'—H1B20.8400
C1A—C6A1.513 (6)O2B'—H2B20.8400
C1A—H1A1.0000P01A—O11A1.488 (2)
C2A—O2A1.442 (5)P01A—C31A1.795 (3)
C2A—C3A1.523 (5)P01A—C21A1.796 (3)
C2A—H2A1.0000P01A—C11A1.809 (3)
C3A—C4A1.536 (6)C11A—C16A1.394 (4)
C3A—H3A10.9900C11A—C12A1.398 (4)
C3A—H3A20.9900C12A—C13A1.385 (4)
C4A—C5A1.522 (5)C12A—H12A0.9500
C4A—H4A10.9900C13A—C14A1.375 (5)
C4A—H4A20.9900C13A—H13A0.9500
C5A—C6A1.513 (6)C14A—C15A1.382 (5)
C5A—H5A10.9900C14A—H14A0.9500
C5A—H5A20.9900C15A—C16A1.394 (4)
C6A—H6A10.9900C15A—H15A0.9500
C6A—H6A20.9900C16A—H16A0.9500
O1A—H1A10.8400C21A—C26A1.376 (5)
O2A—H2A10.8400C21A—C22A1.400 (4)
C1A'—O1A'1.436 (6)C22A—C23A1.379 (5)
C1A'—C2A'1.507 (6)C22A—H22A0.9500
C1A'—C6A'1.514 (8)C23A—C24A1.373 (5)
C1A'—H1A'1.0000C23A—H23A0.9500
C2A'—O2A'1.439 (7)C24A—C25A1.373 (5)
C2A'—C3A'1.523 (6)C24A—H24A0.9500
C2A'—H2A'1.0000C25A—C26A1.394 (4)
C3A'—C4A'1.540 (8)C25A—H25A0.9500
C3A'—H3A30.9900C26A—H26A0.9500
C3A'—H3A40.9900C31A—C36A1.387 (5)
C4A'—C5A'1.526 (6)C31A—C32A1.391 (4)
C4A'—H4A30.9900C32A—C33A1.387 (4)
C4A'—H4A40.9900C32A—H32A0.9500
C5A'—C6A'1.508 (7)C33A—C34A1.382 (5)
C5A'—H5A30.9900C33A—H33A0.9500
C5A'—H5A40.9900C34A—C35A1.382 (5)
C6A'—H6A30.9900C34A—H34A0.9500
C6A'—H6A40.9900C35A—C36A1.391 (4)
O1A'—H1A20.8400C35A—H35A0.9500
O2A'—H2A20.8400C36A—H36A0.9500
C1B—O1B1.435 (5)P01B—O11B1.484 (2)
C1B—C2B1.502 (5)P01B—C21B1.796 (3)
C1B—C6B1.510 (5)P01B—C11B1.803 (3)
C1B—H1B1.0000P01B—C31B1.811 (3)
C2B—O2B1.431 (6)C11B—C16B1.388 (4)
C2B—C3B1.517 (5)C11B—C12B1.396 (4)
C2B—H2B1.0000C12B—C13B1.391 (4)
C3B—C4B1.526 (6)C12B—H12B0.9500
C3B—H3B10.9900C13B—C14B1.373 (5)
C3B—H3B20.9900C13B—H13B0.9500
C4B—C5B1.513 (6)C14B—C15B1.382 (5)
C4B—H4B10.9900C14B—H14B0.9500
C4B—H4B20.9900C15B—C16B1.395 (4)
C5B—C6B1.506 (5)C15B—H15B0.9500
C5B—H5B10.9900C16B—H16B0.9500
C5B—H5B20.9900C21B—C26B1.384 (5)
C6B—H6B10.9900C21B—C22B1.397 (5)
C6B—H6B20.9900C22B—C23B1.393 (5)
O1B—H1B10.8400C22B—H22B0.9500
O2B—H2B10.8400C23B—C24B1.381 (5)
C1B'—O1B'1.434 (7)C23B—H23B0.9500
C1B'—C2B'1.505 (6)C24B—C25B1.376 (5)
C1B'—C6B'1.512 (7)C24B—H24B0.9500
C1B'—H1B'1.0000C25B—C26B1.391 (5)
C2B'—O2B'1.429 (8)C25B—H25B0.9500
C2B'—C3B'1.514 (7)C26B—H26B0.9500
C2B'—H2B'1.0000C31B—C32B1.385 (4)
C3B'—C4B'1.524 (8)C31B—C36B1.394 (5)
C3B'—H3B30.9900C32B—C33B1.387 (5)
C3B'—H3B40.9900C32B—H32B0.9500
C4B'—C5B'1.515 (7)C33B—C34B1.376 (5)
C4B'—H4B30.9900C33B—H33B0.9500
C4B'—H4B40.9900C34B—C35B1.386 (5)
C5B'—C6B'1.509 (6)C34B—H34B0.9500
C5B'—H5B30.9900C35B—C36B1.389 (5)
C5B'—H5B40.9900C35B—H35B0.9500
C6B'—H6B30.9900C36B—H36B0.9500
O1A—C1A—C2A108.3 (4)C6B'—C5B'—C4B'111.3 (8)
O1A—C1A—C6A112.0 (5)C6B'—C5B'—H5B3109.4
C2A—C1A—C6A111.0 (5)C4B'—C5B'—H5B3109.4
O1A—C1A—H1A108.5C6B'—C5B'—H5B4109.4
C2A—C1A—H1A108.5C4B'—C5B'—H5B4109.4
C6A—C1A—H1A108.5H5B3—C5B'—H5B4108.0
O2A—C2A—C1A110.1 (4)C5B'—C6B'—C1B'111.1 (8)
O2A—C2A—C3A108.5 (4)C5B'—C6B'—H6B3109.4
C1A—C2A—C3A110.7 (4)C1B'—C6B'—H6B3109.4
O2A—C2A—H2A109.2C5B'—C6B'—H6B4109.4
C1A—C2A—H2A109.2C1B'—C6B'—H6B4109.4
C3A—C2A—H2A109.2H6B3—C6B'—H6B4108.0
C2A—C3A—C4A110.2 (4)C1B'—O1B'—H1B2109.5
C2A—C3A—H3A1109.6C2B'—O2B'—H2B2109.5
C4A—C3A—H3A1109.6O11A—P01A—C31A111.66 (15)
C2A—C3A—H3A2109.6O11A—P01A—C21A114.16 (14)
C4A—C3A—H3A2109.6C31A—P01A—C21A106.25 (16)
H3A1—C3A—H3A2108.1O11A—P01A—C11A111.71 (15)
C5A—C4A—C3A111.1 (5)C31A—P01A—C11A106.63 (15)
C5A—C4A—H4A1109.4C21A—P01A—C11A105.93 (15)
C3A—C4A—H4A1109.4C16A—C11A—C12A119.9 (3)
C5A—C4A—H4A2109.4C16A—C11A—P01A123.0 (3)
C3A—C4A—H4A2109.4C12A—C11A—P01A117.1 (3)
H4A1—C4A—H4A2108.0C13A—C12A—C11A120.0 (3)
C6A—C5A—C4A110.4 (4)C13A—C12A—H12A120.0
C6A—C5A—H5A1109.6C11A—C12A—H12A120.0
C4A—C5A—H5A1109.6C14A—C13A—C12A120.2 (3)
C6A—C5A—H5A2109.6C14A—C13A—H13A119.9
C4A—C5A—H5A2109.6C12A—C13A—H13A119.9
H5A1—C5A—H5A2108.1C13A—C14A—C15A120.2 (3)
C1A—C6A—C5A111.7 (5)C13A—C14A—H14A119.9
C1A—C6A—H6A1109.3C15A—C14A—H14A119.9
C5A—C6A—H6A1109.3C14A—C15A—C16A120.7 (3)
C1A—C6A—H6A2109.3C14A—C15A—H15A119.7
C5A—C6A—H6A2109.3C16A—C15A—H15A119.7
H6A1—C6A—H6A2107.9C11A—C16A—C15A119.0 (3)
O1A'—C1A'—C2A'109.1 (7)C11A—C16A—H16A120.5
O1A'—C1A'—C6A'110.2 (8)C15A—C16A—H16A120.5
C2A'—C1A'—C6A'111.6 (8)C26A—C21A—C22A118.4 (3)
O1A'—C1A'—H1A'108.6C26A—C21A—P01A123.6 (3)
C2A'—C1A'—H1A'108.6C22A—C21A—P01A118.0 (3)
C6A'—C1A'—H1A'108.6C23A—C22A—C21A120.1 (3)
O2A'—C2A'—C1A'110.7 (8)C23A—C22A—H22A120.0
O2A'—C2A'—C3A'109.1 (8)C21A—C22A—H22A120.0
C1A'—C2A'—C3A'110.7 (6)C24A—C23A—C22A121.0 (4)
O2A'—C2A'—H2A'108.8C24A—C23A—H23A119.5
C1A'—C2A'—H2A'108.8C22A—C23A—H23A119.5
C3A'—C2A'—H2A'108.8C23A—C24A—C25A119.5 (3)
C2A'—C3A'—C4A'109.7 (7)C23A—C24A—H24A120.2
C2A'—C3A'—H3A3109.7C25A—C24A—H24A120.2
C4A'—C3A'—H3A3109.7C24A—C25A—C26A119.9 (4)
C2A'—C3A'—H3A4109.7C24A—C25A—H25A120.0
C4A'—C3A'—H3A4109.7C26A—C25A—H25A120.0
H3A3—C3A'—H3A4108.2C21A—C26A—C25A121.1 (3)
C5A'—C4A'—C3A'109.5 (8)C21A—C26A—H26A119.5
C5A'—C4A'—H4A3109.8C25A—C26A—H26A119.5
C3A'—C4A'—H4A3109.8C36A—C31A—C32A118.2 (3)
C5A'—C4A'—H4A4109.8C36A—C31A—P01A123.2 (3)
C3A'—C4A'—H4A4109.8C32A—C31A—P01A118.5 (3)
H4A3—C4A'—H4A4108.2C33A—C32A—C31A120.9 (3)
C6A'—C5A'—C4A'110.3 (7)C33A—C32A—H32A119.6
C6A'—C5A'—H5A3109.6C31A—C32A—H32A119.6
C4A'—C5A'—H5A3109.6C34A—C33A—C32A120.1 (3)
C6A'—C5A'—H5A4109.6C34A—C33A—H33A120.0
C4A'—C5A'—H5A4109.6C32A—C33A—H33A120.0
H5A3—C5A'—H5A4108.1C35A—C34A—C33A120.0 (3)
C5A'—C6A'—C1A'111.8 (8)C35A—C34A—H34A120.0
C5A'—C6A'—H6A3109.3C33A—C34A—H34A120.0
C1A'—C6A'—H6A3109.3C34A—C35A—C36A119.6 (3)
C5A'—C6A'—H6A4109.3C34A—C35A—H35A120.2
C1A'—C6A'—H6A4109.3C36A—C35A—H35A120.2
H6A3—C6A'—H6A4107.9C31A—C36A—C35A121.2 (3)
C1A'—O1A'—H1A2109.5C31A—C36A—H36A119.4
C2A'—O2A'—H2A2109.5C35A—C36A—H36A119.4
O1B—C1B—C2B111.0 (4)O11B—P01B—C21B113.95 (14)
O1B—C1B—C6B109.5 (4)O11B—P01B—C11B112.03 (14)
C2B—C1B—C6B111.8 (4)C21B—P01B—C11B105.92 (15)
O1B—C1B—H1B108.1O11B—P01B—C31B111.59 (15)
C2B—C1B—H1B108.1C21B—P01B—C31B106.20 (16)
C6B—C1B—H1B108.1C11B—P01B—C31B106.65 (15)
O2B—C2B—C1B108.9 (4)C16B—C11B—C12B119.5 (3)
O2B—C2B—C3B111.7 (5)C16B—C11B—P01B123.6 (3)
C1B—C2B—C3B111.2 (4)C12B—C11B—P01B116.9 (2)
O2B—C2B—H2B108.3C13B—C12B—C11B120.1 (3)
C1B—C2B—H2B108.3C13B—C12B—H12B120.0
C3B—C2B—H2B108.3C11B—C12B—H12B120.0
C2B—C3B—C4B110.5 (4)C14B—C13B—C12B120.4 (3)
C2B—C3B—H3B1109.6C14B—C13B—H13B119.8
C4B—C3B—H3B1109.6C12B—C13B—H13B119.8
C2B—C3B—H3B2109.6C13B—C14B—C15B119.8 (3)
C4B—C3B—H3B2109.6C13B—C14B—H14B120.1
H3B1—C3B—H3B2108.1C15B—C14B—H14B120.1
C5B—C4B—C3B111.7 (5)C14B—C15B—C16B120.7 (3)
C5B—C4B—H4B1109.3C14B—C15B—H15B119.7
C3B—C4B—H4B1109.3C16B—C15B—H15B119.7
C5B—C4B—H4B2109.3C11B—C16B—C15B119.5 (3)
C3B—C4B—H4B2109.3C11B—C16B—H16B120.2
H4B1—C4B—H4B2107.9C15B—C16B—H16B120.2
C6B—C5B—C4B112.2 (4)C26B—C21B—C22B118.8 (3)
C6B—C5B—H5B1109.2C26B—C21B—P01B123.2 (3)
C4B—C5B—H5B1109.2C22B—C21B—P01B118.0 (3)
C6B—C5B—H5B2109.2C23B—C22B—C21B120.5 (4)
C4B—C5B—H5B2109.2C23B—C22B—H22B119.8
H5B1—C5B—H5B2107.9C21B—C22B—H22B119.8
C5B—C6B—C1B112.1 (4)C24B—C23B—C22B119.8 (4)
C5B—C6B—H6B1109.2C24B—C23B—H23B120.1
C1B—C6B—H6B1109.2C22B—C23B—H23B120.1
C5B—C6B—H6B2109.2C25B—C24B—C23B120.0 (4)
C1B—C6B—H6B2109.2C25B—C24B—H24B120.0
H6B1—C6B—H6B2107.9C23B—C24B—H24B120.0
O1B'—C1B'—C2B'110.4 (8)C24B—C25B—C26B120.3 (4)
O1B'—C1B'—C6B'110.4 (8)C24B—C25B—H25B119.9
C2B'—C1B'—C6B'111.0 (8)C26B—C25B—H25B119.9
O1B'—C1B'—H1B'108.3C21B—C26B—C25B120.5 (3)
C2B'—C1B'—H1B'108.3C21B—C26B—H26B119.7
C6B'—C1B'—H1B'108.3C25B—C26B—H26B119.7
O2B'—C2B'—C1B'108.9 (9)C32B—C31B—C36B119.2 (3)
O2B'—C2B'—C3B'112.3 (9)C32B—C31B—P01B118.0 (3)
C1B'—C2B'—C3B'111.3 (7)C36B—C31B—P01B122.8 (3)
O2B'—C2B'—H2B'108.1C31B—C32B—C33B120.7 (3)
C1B'—C2B'—H2B'108.1C31B—C32B—H32B119.6
C3B'—C2B'—H2B'108.1C33B—C32B—H32B119.6
C2B'—C3B'—C4B'111.6 (9)C34B—C33B—C32B119.8 (3)
C2B'—C3B'—H3B3109.3C34B—C33B—H33B120.1
C4B'—C3B'—H3B3109.3C32B—C33B—H33B120.1
C2B'—C3B'—H3B4109.3C33B—C34B—C35B120.2 (3)
C4B'—C3B'—H3B4109.3C33B—C34B—H34B119.9
H3B3—C3B'—H3B4108.0C35B—C34B—H34B119.9
C5B'—C4B'—C3B'111.8 (9)C34B—C35B—C36B120.1 (4)
C5B'—C4B'—H4B3109.3C34B—C35B—H35B120.0
C3B'—C4B'—H4B3109.3C36B—C35B—H35B120.0
C5B'—C4B'—H4B4109.3C35B—C36B—C31B120.0 (3)
C3B'—C4B'—H4B4109.3C35B—C36B—H36B120.0
H4B3—C4B'—H4B4107.9C31B—C36B—H36B120.0
O1A—C1A—C2A—O2A59.6 (7)C26A—C21A—C22A—C23A1.3 (5)
C6A—C1A—C2A—O2A177.1 (5)P01A—C21A—C22A—C23A175.8 (3)
O1A—C1A—C2A—C3A179.6 (4)C21A—C22A—C23A—C24A0.6 (6)
C6A—C1A—C2A—C3A57.1 (8)C22A—C23A—C24A—C25A0.3 (6)
O2A—C2A—C3A—C4A177.8 (5)C23A—C24A—C25A—C26A0.5 (6)
C1A—C2A—C3A—C4A56.8 (8)C22A—C21A—C26A—C25A1.1 (5)
C2A—C3A—C4A—C5A56.4 (9)P01A—C21A—C26A—C25A175.8 (3)
C3A—C4A—C5A—C6A55.6 (10)C24A—C25A—C26A—C21A0.2 (6)
O1A—C1A—C6A—C5A178.0 (5)O11A—P01A—C31A—C36A158.8 (3)
C2A—C1A—C6A—C5A56.9 (10)C21A—P01A—C31A—C36A76.1 (3)
C4A—C5A—C6A—C1A55.8 (10)C11A—P01A—C31A—C36A36.6 (3)
O1A'—C1A'—C2A'—O2A'61.2 (13)O11A—P01A—C31A—C32A20.3 (3)
C6A'—C1A'—C2A'—O2A'176.7 (13)C21A—P01A—C31A—C32A104.8 (3)
O1A'—C1A'—C2A'—C3A'177.6 (9)C11A—P01A—C31A—C32A142.6 (3)
C6A'—C1A'—C2A'—C3A'55.6 (14)C36A—C31A—C32A—C33A1.3 (5)
O2A'—C2A'—C3A'—C4A'179.9 (12)P01A—C31A—C32A—C33A177.9 (3)
C1A'—C2A'—C3A'—C4A'57.9 (13)C31A—C32A—C33A—C34A0.6 (5)
C2A'—C3A'—C4A'—C5A'59.3 (17)C32A—C33A—C34A—C35A1.1 (5)
C3A'—C4A'—C5A'—C6A'58.5 (16)C33A—C34A—C35A—C36A2.0 (5)
C4A'—C5A'—C6A'—C1A'56.3 (17)C32A—C31A—C36A—C35A0.4 (5)
O1A'—C1A'—C6A'—C5A'176.4 (12)P01A—C31A—C36A—C35A178.7 (3)
C2A'—C1A'—C6A'—C5A'55.0 (19)C34A—C35A—C36A—C31A1.3 (5)
O1B—C1B—C2B—O2B57.9 (8)O11B—P01B—C11B—C16B158.4 (3)
C6B—C1B—C2B—O2B179.5 (5)C21B—P01B—C11B—C16B33.6 (3)
O1B—C1B—C2B—C3B178.7 (4)C31B—P01B—C11B—C16B79.3 (3)
C6B—C1B—C2B—C3B56.1 (8)O11B—P01B—C11B—C12B22.0 (3)
O2B—C2B—C3B—C4B178.2 (6)C21B—P01B—C11B—C12B146.8 (3)
C1B—C2B—C3B—C4B56.3 (9)C31B—P01B—C11B—C12B100.4 (3)
C2B—C3B—C4B—C5B54.8 (10)C16B—C11B—C12B—C13B1.0 (5)
C3B—C4B—C5B—C6B53.0 (11)P01B—C11B—C12B—C13B178.7 (2)
C4B—C5B—C6B—C1B52.2 (10)C11B—C12B—C13B—C14B1.0 (5)
O1B—C1B—C6B—C5B177.2 (4)C12B—C13B—C14B—C15B1.7 (5)
C2B—C1B—C6B—C5B53.8 (9)C13B—C14B—C15B—C16B0.5 (5)
O1B'—C1B'—C2B'—O2B'56.5 (18)C12B—C11B—C16B—C15B2.2 (5)
C6B'—C1B'—C2B'—O2B'179.2 (17)P01B—C11B—C16B—C15B177.5 (2)
O1B'—C1B'—C2B'—C3B'179.2 (12)C14B—C15B—C16B—C11B1.5 (5)
C6B'—C1B'—C2B'—C3B'56.4 (15)O11B—P01B—C21B—C26B113.8 (3)
O2B'—C2B'—C3B'—C4B'176.6 (19)C11B—P01B—C21B—C26B122.6 (3)
C1B'—C2B'—C3B'—C4B'54.2 (18)C31B—P01B—C21B—C26B9.4 (3)
C2B'—C3B'—C4B'—C5B'53 (2)O11B—P01B—C21B—C22B63.1 (3)
C3B'—C4B'—C5B'—C6B'54 (2)C11B—P01B—C21B—C22B60.5 (3)
C4B'—C5B'—C6B'—C1B'55.9 (18)C31B—P01B—C21B—C22B173.7 (3)
O1B'—C1B'—C6B'—C5B'179.9 (14)C26B—C21B—C22B—C23B0.7 (5)
C2B'—C1B'—C6B'—C5B'57.4 (18)P01B—C21B—C22B—C23B176.3 (3)
O11A—P01A—C11A—C16A158.2 (3)C21B—C22B—C23B—C24B0.6 (6)
C31A—P01A—C11A—C16A79.6 (3)C22B—C23B—C24B—C25B1.6 (6)
C21A—P01A—C11A—C16A33.3 (3)C23B—C24B—C25B—C26B1.2 (6)
O11A—P01A—C11A—C12A22.9 (3)C22B—C21B—C26B—C25B1.1 (5)
C31A—P01A—C11A—C12A99.3 (3)P01B—C21B—C26B—C25B175.8 (3)
C21A—P01A—C11A—C12A147.8 (3)C24B—C25B—C26B—C21B0.1 (5)
C16A—C11A—C12A—C13A1.6 (5)O11B—P01B—C31B—C32B21.2 (3)
P01A—C11A—C12A—C13A177.3 (2)C21B—P01B—C31B—C32B103.5 (3)
C11A—C12A—C13A—C14A0.5 (5)C11B—P01B—C31B—C32B143.9 (3)
C12A—C13A—C14A—C15A0.1 (5)O11B—P01B—C31B—C36B157.9 (3)
C13A—C14A—C15A—C16A0.7 (5)C21B—P01B—C31B—C36B77.4 (3)
C12A—C11A—C16A—C15A2.3 (5)C11B—P01B—C31B—C36B35.3 (3)
P01A—C11A—C16A—C15A176.7 (2)C36B—C31B—C32B—C33B0.8 (5)
C14A—C15A—C16A—C11A1.8 (5)P01B—C31B—C32B—C33B178.3 (3)
O11A—P01A—C21A—C26A114.5 (3)C31B—C32B—C33B—C34B0.2 (5)
C31A—P01A—C21A—C26A9.0 (3)C32B—C33B—C34B—C35B0.9 (5)
C11A—P01A—C21A—C26A122.1 (3)C33B—C34B—C35B—C36B1.5 (5)
O11A—P01A—C21A—C22A62.4 (3)C34B—C35B—C36B—C31B0.9 (5)
C31A—P01A—C21A—C22A174.1 (3)C32B—C31B—C36B—C35B0.3 (5)
C11A—P01A—C21A—C22A60.9 (3)P01B—C31B—C36B—C35B178.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A1···O1Bi0.841.912.746 (7)171
O2A—H2A1···O1Aii0.841.892.708 (6)164
O1B—H1B1···O2Bi0.841.972.761 (9)157
O2B—H2B1···O2Aii0.841.912.737 (8)169
O1A—H1A2···O2Aii0.842.132.786 (17)135
O2A—H2A2···O2Bii0.841.912.73 (2)166
O1B—H1B2···O1Ai0.841.912.74 (2)174
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.
(toluene90KtriCuKa) 1:1 rac-1,2-cyclohexanediol triphenylphosphine oxide top
Crystal data top
C6H12O2·C18H15OPZ = 4
Mr = 394.43F(000) = 840
Triclinic, P1Dx = 1.267 Mg m3
a = 9.271 (1) ÅCu Kα radiation, λ = 1.54178 Å
b = 10.923 (1) ÅCell parameters from 7792 reflections
c = 21.306 (2) Åθ = 2.2–67.8°
α = 100.77 (1)°µ = 1.35 mm1
β = 102.53 (1)°T = 90 K
γ = 90.02 (1)°Lath, colorless
V = 2067.2 (4) Å30.20 × 0.12 × 0.04 mm
Data collection top
Bruker-Nonius X8 Proteum
diffractometer
7346 independent reflections
Radiation source: fine-focus rotating anode6312 reflections with I > 2σ(I)
Graded multi-layer optics monochromatorRint = 0.055
Detector resolution: 18 pixels mm-1θmax = 68.2°, θmin = 2.2°
ω and ϕ scansh = 1011
Absorption correction: multi-scan
SADABS in APEX2 (Bruker-Nonius, 2004)
k = 1313
Tmin = 0.77, Tmax = 0.95l = 2525
28054 measured 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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0363P)2 + 0.8227P]
where P = (Fo2 + 2Fc2)/3
7346 reflections(Δ/σ)max = 0.002
564 parametersΔρmax = 0.29 e Å3
148 restraintsΔρmin = 0.42 e Å3
Crystal data top
C6H12O2·C18H15OPγ = 90.02 (1)°
Mr = 394.43V = 2067.2 (4) Å3
Triclinic, P1Z = 4
a = 9.271 (1) ÅCu Kα radiation
b = 10.923 (1) ŵ = 1.35 mm1
c = 21.306 (2) ÅT = 90 K
α = 100.77 (1)°0.20 × 0.12 × 0.04 mm
β = 102.53 (1)°
Data collection top
Bruker-Nonius X8 Proteum
diffractometer
7346 independent reflections
Absorption correction: multi-scan
SADABS in APEX2 (Bruker-Nonius, 2004)
6312 reflections with I > 2σ(I)
Tmin = 0.77, Tmax = 0.95Rint = 0.055
28054 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.039148 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.04Δρmax = 0.29 e Å3
7346 reflectionsΔρmin = 0.42 e Å3
564 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.7768 (6)0.0761 (5)0.0370 (2)0.0233 (11)0.689 (5)
H1A0.82900.05700.00010.028*0.689 (5)
C2A0.7481 (5)0.0446 (5)0.0583 (2)0.0234 (12)0.689 (5)
H2A0.69160.02660.09380.028*0.689 (5)
C3A0.8917 (6)0.1030 (5)0.0844 (3)0.0263 (11)0.689 (5)
H3A10.94520.12700.04880.032*0.689 (5)
H3A20.86990.17950.10000.032*0.689 (5)
C4A0.9889 (8)0.0113 (6)0.1408 (4)0.0363 (18)0.689 (5)
H4A10.93970.00560.17810.044*0.689 (5)
H4A21.08450.04900.15540.044*0.689 (5)
C5A1.0170 (6)0.1102 (5)0.1199 (3)0.0337 (11)0.689 (5)
H5A11.07450.16960.15800.040*0.689 (5)
H5A21.07670.09460.08610.040*0.689 (5)
C6A0.8740 (7)0.1676 (5)0.0926 (4)0.0304 (16)0.689 (5)
H6A10.89650.24310.07650.037*0.689 (5)
H6A20.82000.19310.12800.037*0.689 (5)
O1A0.6377 (5)0.1250 (5)0.0136 (2)0.0288 (10)0.689 (5)
H1A10.64920.20120.01340.043*0.689 (5)
O2A0.6611 (5)0.1328 (5)0.0037 (3)0.0323 (12)0.689 (5)
H2A10.57110.11760.00030.048*0.689 (5)
C1A'0.7469 (11)0.0874 (9)0.0552 (5)0.0233 (11)0.311 (5)
H1A'0.68330.10350.08800.028*0.311 (5)
C2A'0.7742 (12)0.0507 (9)0.0415 (5)0.0234 (12)0.311 (5)
H2A'0.83310.06820.00700.028*0.311 (5)
C3A'0.8586 (13)0.0918 (10)0.1032 (5)0.0263 (11)0.311 (5)
H3A30.87740.18180.09310.032*0.311 (5)
H3A40.79860.07890.13690.032*0.311 (5)
C4A'1.0059 (15)0.0169 (11)0.1296 (10)0.0363 (18)0.311 (5)
H4A31.05940.04300.17020.044*0.311 (5)
H4A41.06820.03320.09690.044*0.311 (5)
C5A'0.9775 (14)0.1215 (11)0.1440 (5)0.0337 (11)0.311 (5)
H5A30.92040.13830.17880.040*0.311 (5)
H5A41.07300.16970.16020.040*0.311 (5)
C6A'0.8923 (18)0.1632 (11)0.0831 (9)0.0304 (16)0.311 (5)
H6A30.95300.15300.04970.037*0.311 (5)
H6A40.87170.25270.09390.037*0.311 (5)
O1A'0.6710 (11)0.1231 (11)0.0038 (5)0.0288 (10)0.311 (5)
H1A20.58150.09970.01180.043*0.311 (5)
O2A'0.6343 (13)0.1220 (12)0.0188 (6)0.0323 (12)0.311 (5)
H2A20.62790.17090.04430.048*0.311 (5)
C1B0.3082 (6)0.5890 (4)0.0525 (2)0.0249 (10)0.765 (6)
H1B0.40490.60640.08500.030*0.765 (6)
C2B0.2698 (6)0.4509 (4)0.0403 (2)0.0256 (10)0.765 (6)
H2B0.17480.43230.00680.031*0.765 (6)
C3B0.2501 (8)0.4129 (6)0.1029 (3)0.0396 (15)0.765 (6)
H3B10.34490.42710.13580.048*0.765 (6)
H3B20.22210.32280.09400.048*0.765 (6)
C4B0.1311 (9)0.4875 (6)0.1303 (3)0.0392 (15)0.765 (6)
H4B10.03430.46640.09920.047*0.765 (6)
H4B20.12400.46400.17220.047*0.765 (6)
C5B0.1643 (7)0.6269 (5)0.1415 (2)0.0347 (11)0.765 (6)
H5B10.07960.67220.15440.042*0.765 (6)
H5B20.25230.65030.17770.042*0.765 (6)
C6B0.1924 (9)0.6649 (5)0.0802 (3)0.0312 (14)0.765 (6)
H6B10.09880.65510.04660.037*0.765 (6)
H6B20.22480.75410.09050.037*0.765 (6)
O1B0.3232 (6)0.6273 (4)0.0069 (2)0.0314 (9)0.765 (6)
H1B10.40530.60620.01510.047*0.765 (6)
O2B0.3849 (7)0.3867 (5)0.0148 (3)0.0361 (14)0.765 (6)
H2B10.36680.30950.00800.054*0.765 (6)
C1B'0.2628 (15)0.5744 (11)0.0372 (6)0.0249 (10)0.235 (6)
H1B'0.17450.55120.00030.030*0.235 (6)
C2B'0.3194 (15)0.4569 (11)0.0604 (6)0.0256 (10)0.235 (6)
H2B'0.41220.47810.09510.031*0.235 (6)
C3B'0.205 (2)0.3980 (12)0.0880 (10)0.0396 (15)0.235 (6)
H3B30.24740.32540.10610.048*0.235 (6)
H3B40.11820.36730.05230.048*0.235 (6)
C4B'0.155 (3)0.4895 (18)0.1415 (10)0.0392 (15)0.235 (6)
H4B30.07450.44950.15520.047*0.235 (6)
H4B40.23890.51040.18010.047*0.235 (6)
C5B'0.1018 (18)0.6083 (16)0.1188 (8)0.0347 (11)0.235 (6)
H5B30.00900.58950.08480.042*0.235 (6)
H5B40.08030.66860.15620.042*0.235 (6)
C6B'0.217 (3)0.6658 (12)0.0912 (11)0.0312 (14)0.235 (6)
H6B30.17660.73960.07380.037*0.235 (6)
H6B40.30510.69420.12680.037*0.235 (6)
O1B'0.3750 (16)0.6317 (13)0.0137 (7)0.0314 (9)0.235 (6)
H1B20.34610.70000.00400.047*0.235 (6)
O2B'0.352 (3)0.3747 (16)0.0050 (11)0.0361 (14)0.235 (6)
H2B20.28670.37900.02860.054*0.235 (6)
P01A0.78765 (11)0.16216 (9)0.33633 (4)0.0171 (2)
O11A0.8436 (3)0.2924 (2)0.34179 (11)0.0225 (6)
C11A0.6314 (4)0.1190 (4)0.26765 (16)0.0196 (8)
C12A0.6175 (4)0.1848 (4)0.21676 (16)0.0224 (8)
H12A0.68650.25120.21980.027*
C13A0.5037 (5)0.1542 (4)0.16166 (18)0.0285 (10)
H13A0.49360.20010.12730.034*
C14A0.4043 (5)0.0555 (5)0.15693 (18)0.0326 (11)
H14A0.32730.03300.11880.039*
C15A0.4172 (5)0.0098 (4)0.20758 (18)0.0260 (9)
H15A0.34870.07670.20400.031*
C16A0.5297 (4)0.0218 (3)0.26372 (16)0.0205 (8)
H16A0.53720.02200.29880.025*
C21A0.7255 (4)0.1355 (4)0.40757 (16)0.0191 (8)
C22A0.6052 (5)0.2014 (4)0.42420 (18)0.0300 (9)
H22A0.55460.25380.39650.036*
C23A0.5600 (5)0.1910 (4)0.48002 (19)0.0333 (10)
H23A0.47900.23700.49100.040*
C24A0.6308 (6)0.1142 (4)0.52069 (17)0.0291 (9)
H24A0.59960.10800.55970.035*
C25A0.7473 (5)0.0466 (4)0.50415 (18)0.0317 (11)
H25A0.79520.00720.53170.038*
C26A0.7958 (5)0.0560 (4)0.44743 (18)0.0262 (9)
H26A0.87570.00880.43630.031*
C31A0.9265 (4)0.0509 (4)0.32379 (16)0.0185 (8)
C32A1.0749 (4)0.0949 (4)0.34163 (16)0.0209 (8)
H32A1.09920.18010.36080.025*
C33A1.1861 (5)0.0130 (4)0.33118 (18)0.0249 (9)
H33A1.28650.04270.34330.030*
C34A1.1517 (5)0.1106 (4)0.30336 (18)0.0271 (10)
H34A1.22820.16530.29550.033*
C35A1.0052 (5)0.1559 (4)0.28674 (17)0.0275 (9)
H35A0.98190.24170.26850.033*
C36A0.8928 (5)0.0747 (4)0.29689 (18)0.0267 (9)
H36A0.79270.10530.28540.032*
P01B0.54991 (11)0.66131 (9)0.33487 (4)0.0173 (2)
O11B0.4987 (3)0.7907 (2)0.34052 (11)0.0230 (6)
C11B0.6390 (4)0.6192 (4)0.26696 (15)0.0178 (8)
C12B0.6053 (4)0.6867 (4)0.21642 (15)0.0230 (9)
H12B0.53960.75330.21940.028*
C13B0.6668 (5)0.6573 (4)0.16210 (18)0.0304 (10)
H13B0.64430.70440.12820.036*
C14B0.7604 (5)0.5603 (4)0.15712 (18)0.0299 (10)
H14B0.80030.53900.11920.036*
C15B0.7969 (5)0.4932 (4)0.20723 (18)0.0279 (9)
H15B0.86300.42700.20390.033*
C16B0.7368 (4)0.5230 (3)0.26233 (16)0.0229 (8)
H16B0.76240.47760.29680.028*
C21B0.6816 (5)0.6336 (4)0.40591 (16)0.0205 (8)
C22B0.8159 (5)0.7008 (4)0.42376 (17)0.0284 (10)
H22B0.83810.75610.39730.034*
C23B0.9188 (5)0.6877 (4)0.4804 (2)0.0369 (11)
H23B1.01170.73220.49170.044*
C24B0.8849 (6)0.6095 (4)0.52012 (17)0.0323 (10)
H24B0.95340.60220.55930.039*
C25B0.7518 (5)0.5426 (4)0.50244 (19)0.0312 (10)
H25B0.72880.48810.52910.037*
C26B0.6516 (5)0.5548 (4)0.44583 (17)0.0262 (9)
H26B0.56010.50820.43400.031*
C31B0.3958 (4)0.5481 (4)0.32104 (17)0.0205 (8)
C32B0.2677 (5)0.5904 (4)0.34002 (16)0.0215 (8)
H32B0.26300.67510.36010.026*
C33B0.1463 (5)0.5087 (4)0.32964 (18)0.0266 (10)
H33B0.05820.53800.34220.032*
C34B0.1532 (5)0.3846 (4)0.30101 (18)0.0287 (10)
H34B0.06980.32900.29350.034*
C35B0.2822 (5)0.3423 (4)0.28349 (17)0.0284 (9)
H35B0.28790.25690.26470.034*
C36B0.4027 (5)0.4232 (4)0.29312 (18)0.0225 (8)
H36B0.49070.39350.28070.027*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.019 (2)0.0279 (17)0.022 (2)0.0032 (15)0.0031 (16)0.0025 (16)
C2A0.022 (2)0.0256 (17)0.022 (2)0.0041 (15)0.0033 (17)0.0046 (16)
C3A0.018 (2)0.031 (2)0.032 (2)0.0050 (16)0.0083 (16)0.0087 (18)
C4A0.028 (3)0.050 (2)0.030 (3)0.004 (2)0.005 (2)0.017 (2)
C5A0.024 (2)0.046 (2)0.028 (3)0.0064 (18)0.0015 (17)0.004 (2)
C6A0.028 (2)0.0258 (19)0.035 (3)0.0065 (16)0.005 (2)0.0006 (16)
O1A0.0171 (18)0.0322 (16)0.038 (2)0.0058 (14)0.0052 (14)0.0096 (16)
O2A0.024 (2)0.0335 (17)0.034 (3)0.0046 (15)0.0002 (16)0.0000 (16)
C1A'0.019 (2)0.0279 (17)0.022 (2)0.0032 (15)0.0031 (16)0.0025 (16)
C2A'0.022 (2)0.0256 (17)0.022 (2)0.0041 (15)0.0033 (17)0.0046 (16)
C3A'0.018 (2)0.031 (2)0.032 (2)0.0050 (16)0.0083 (16)0.0087 (18)
C4A'0.028 (3)0.050 (2)0.030 (3)0.004 (2)0.005 (2)0.017 (2)
C5A'0.024 (2)0.046 (2)0.028 (3)0.0064 (18)0.0015 (17)0.004 (2)
C6A'0.028 (2)0.0258 (19)0.035 (3)0.0065 (16)0.005 (2)0.0006 (16)
O1A'0.0171 (18)0.0322 (16)0.038 (2)0.0058 (14)0.0052 (14)0.0096 (16)
O2A'0.024 (2)0.0335 (17)0.034 (3)0.0046 (15)0.0002 (16)0.0000 (16)
C1B0.023 (2)0.0261 (17)0.022 (2)0.0051 (16)0.0042 (17)0.0025 (15)
C2B0.023 (2)0.0291 (18)0.026 (2)0.0037 (16)0.0078 (18)0.0050 (15)
C3B0.044 (4)0.040 (2)0.045 (3)0.012 (2)0.022 (3)0.022 (2)
C4B0.040 (4)0.049 (2)0.036 (3)0.005 (2)0.020 (3)0.016 (2)
C5B0.031 (3)0.050 (2)0.022 (2)0.0045 (19)0.0106 (19)0.0020 (17)
C6B0.034 (3)0.0291 (19)0.031 (3)0.0028 (17)0.012 (2)0.0026 (15)
O1B0.042 (2)0.0292 (16)0.0266 (18)0.0019 (15)0.0166 (16)0.0036 (14)
O2B0.040 (3)0.0298 (17)0.043 (2)0.0110 (18)0.019 (2)0.0068 (14)
C1B'0.023 (2)0.0261 (17)0.022 (2)0.0051 (16)0.0042 (17)0.0025 (15)
C2B'0.023 (2)0.0291 (18)0.026 (2)0.0037 (16)0.0078 (18)0.0050 (15)
C3B'0.044 (4)0.040 (2)0.045 (3)0.012 (2)0.022 (3)0.022 (2)
C4B'0.040 (4)0.049 (2)0.036 (3)0.005 (2)0.020 (3)0.016 (2)
C5B'0.031 (3)0.050 (2)0.022 (2)0.0045 (19)0.0106 (19)0.0020 (17)
C6B'0.034 (3)0.0291 (19)0.031 (3)0.0028 (17)0.012 (2)0.0026 (15)
O1B'0.042 (2)0.0292 (16)0.0266 (18)0.0019 (15)0.0166 (16)0.0036 (14)
O2B'0.040 (3)0.0298 (17)0.043 (2)0.0110 (18)0.019 (2)0.0068 (14)
P01A0.0145 (5)0.0184 (5)0.0174 (4)0.0002 (5)0.0013 (5)0.0034 (3)
O11A0.0213 (14)0.0228 (14)0.0217 (11)0.0035 (12)0.0003 (12)0.0053 (10)
C11A0.020 (2)0.022 (2)0.0199 (16)0.0042 (16)0.0089 (16)0.0045 (14)
C12A0.021 (2)0.024 (2)0.0235 (17)0.0025 (16)0.0076 (16)0.0029 (14)
C13A0.033 (2)0.036 (2)0.0184 (17)0.0092 (19)0.0067 (17)0.0090 (16)
C14A0.022 (2)0.050 (3)0.0198 (18)0.003 (2)0.0022 (17)0.0026 (18)
C15A0.0181 (19)0.028 (2)0.0276 (18)0.0052 (18)0.0037 (17)0.0032 (16)
C16A0.0183 (19)0.0204 (19)0.0235 (16)0.0040 (18)0.0050 (16)0.0057 (14)
C21A0.0147 (18)0.022 (2)0.0185 (16)0.0059 (16)0.0017 (15)0.0003 (14)
C22A0.031 (2)0.033 (2)0.0287 (19)0.010 (2)0.013 (2)0.0040 (17)
C23A0.037 (2)0.032 (2)0.0308 (19)0.007 (2)0.012 (2)0.0002 (17)
C24A0.035 (2)0.031 (2)0.0221 (17)0.010 (2)0.016 (2)0.0046 (15)
C25A0.037 (3)0.039 (3)0.0201 (17)0.006 (2)0.0028 (17)0.0126 (17)
C26A0.019 (2)0.032 (2)0.0299 (19)0.0015 (17)0.0063 (17)0.0106 (16)
C31A0.0195 (19)0.020 (2)0.0167 (16)0.0001 (17)0.0034 (16)0.0052 (14)
C32A0.0143 (19)0.032 (2)0.0171 (15)0.0021 (17)0.0019 (15)0.0070 (14)
C33A0.018 (2)0.034 (3)0.0256 (19)0.0010 (17)0.0060 (17)0.0107 (17)
C34A0.020 (2)0.038 (3)0.0262 (19)0.0116 (18)0.0082 (17)0.0106 (17)
C35A0.034 (2)0.020 (2)0.0303 (18)0.0098 (19)0.0091 (19)0.0086 (15)
C36A0.019 (2)0.035 (2)0.0249 (18)0.0016 (19)0.0053 (17)0.0036 (16)
P01B0.0156 (5)0.0186 (5)0.0169 (4)0.0005 (5)0.0022 (5)0.0031 (3)
O11B0.0200 (14)0.0206 (14)0.0282 (12)0.0001 (12)0.0052 (12)0.0045 (10)
C11B0.0128 (19)0.019 (2)0.0203 (16)0.0064 (15)0.0047 (15)0.0018 (13)
C12B0.021 (2)0.027 (2)0.0183 (16)0.0040 (17)0.0012 (16)0.0060 (14)
C13B0.026 (2)0.045 (3)0.0193 (17)0.0051 (19)0.0049 (16)0.0042 (16)
C14B0.022 (2)0.046 (3)0.0204 (18)0.0067 (19)0.0070 (17)0.0017 (17)
C15B0.0194 (19)0.033 (2)0.0302 (19)0.0037 (18)0.0084 (17)0.0008 (17)
C16B0.0147 (19)0.028 (2)0.0235 (17)0.0023 (19)0.0033 (16)0.0001 (15)
C21B0.026 (2)0.018 (2)0.0162 (15)0.0003 (17)0.0031 (16)0.0006 (14)
C22B0.032 (2)0.026 (2)0.0252 (18)0.005 (2)0.002 (2)0.0083 (16)
C23B0.028 (2)0.037 (3)0.034 (2)0.008 (2)0.014 (2)0.0023 (18)
C24B0.038 (2)0.037 (2)0.0180 (16)0.006 (2)0.001 (2)0.0022 (15)
C25B0.026 (2)0.040 (3)0.0272 (18)0.0024 (19)0.0015 (17)0.0111 (18)
C26B0.027 (2)0.031 (2)0.0195 (16)0.0027 (18)0.0021 (16)0.0046 (15)
C31B0.0176 (19)0.028 (2)0.0160 (16)0.0004 (18)0.0003 (15)0.0086 (15)
C32B0.021 (2)0.0208 (19)0.0224 (16)0.0037 (17)0.0020 (16)0.0065 (14)
C33B0.015 (2)0.043 (3)0.0253 (19)0.0027 (18)0.0069 (17)0.0144 (18)
C34B0.024 (2)0.034 (3)0.028 (2)0.0077 (18)0.0029 (18)0.0157 (18)
C35B0.026 (2)0.027 (2)0.0298 (18)0.0017 (19)0.0034 (18)0.0004 (15)
C36B0.025 (2)0.017 (2)0.0271 (18)0.0005 (17)0.0098 (17)0.0033 (15)
Geometric parameters (Å, º) top
C1A—O1A1.421 (5)C6B'—H6B40.9900
C1A—C2A1.513 (5)O1B'—H1B20.8400
C1A—C6A1.519 (7)O2B'—H2B20.8400
C1A—H1A1.0000P01A—O11A1.489 (3)
C2A—O2A1.452 (6)P01A—C31A1.798 (4)
C2A—C3A1.517 (5)P01A—C21A1.807 (4)
C2A—H2A1.0000P01A—C11A1.812 (4)
C3A—C4A1.529 (7)C11A—C12A1.393 (5)
C3A—H3A10.9900C11A—C16A1.399 (6)
C3A—H3A20.9900C12A—C13A1.385 (5)
C4A—C5A1.516 (6)C12A—H12A0.9500
C4A—H4A10.9900C13A—C14A1.392 (7)
C4A—H4A20.9900C13A—H13A0.9500
C5A—C6A1.514 (6)C14A—C15A1.386 (6)
C5A—H5A10.9900C14A—H14A0.9500
C5A—H5A20.9900C15A—C16A1.393 (5)
C6A—H6A10.9900C15A—H15A0.9500
C6A—H6A20.9900C16A—H16A0.9500
O1A—H1A10.8400C21A—C26A1.391 (5)
O2A—H2A10.8400C21A—C22A1.402 (6)
C1A'—O1A'1.424 (7)C22A—C23A1.367 (6)
C1A'—C2A'1.513 (7)C22A—H22A0.9500
C1A'—C6A'1.524 (9)C23A—C24A1.383 (6)
C1A'—H1A'1.0000C23A—H23A0.9500
C2A'—O2A'1.452 (7)C24A—C25A1.379 (7)
C2A'—C3A'1.521 (7)C24A—H24A0.9500
C2A'—H2A'1.0000C25A—C26A1.399 (5)
C3A'—C4A'1.531 (9)C25A—H25A0.9500
C3A'—H3A30.9900C26A—H26A0.9500
C3A'—H3A40.9900C31A—C36A1.392 (6)
C4A'—C5A'1.520 (7)C31A—C32A1.404 (6)
C4A'—H4A30.9900C32A—C33A1.393 (6)
C4A'—H4A40.9900C32A—H32A0.9500
C5A'—C6A'1.515 (7)C33A—C34A1.377 (6)
C5A'—H5A30.9900C33A—H33A0.9500
C5A'—H5A40.9900C34A—C35A1.393 (7)
C6A'—H6A30.9900C34A—H34A0.9500
C6A'—H6A40.9900C35A—C36A1.395 (6)
O1A'—H1A20.8400C35A—H35A0.9500
O2A'—H2A20.8400C36A—H36A0.9500
C1B—O1B1.440 (5)P01B—O11B1.482 (3)
C1B—C6B1.510 (7)P01B—C21B1.801 (4)
C1B—C2B1.511 (5)P01B—C11B1.805 (4)
C1B—H1B1.0000P01B—C31B1.827 (4)
C2B—O2B1.427 (6)C11B—C16B1.391 (6)
C2B—C3B1.515 (6)C11B—C12B1.398 (5)
C2B—H2B1.0000C12B—C13B1.384 (5)
C3B—C4B1.524 (7)C12B—H12B0.9500
C3B—H3B10.9900C13B—C14B1.373 (7)
C3B—H3B20.9900C13B—H13B0.9500
C4B—C5B1.518 (6)C14B—C15B1.388 (6)
C4B—H4B10.9900C14B—H14B0.9500
C4B—H4B20.9900C15B—C16B1.392 (5)
C5B—C6B1.515 (6)C15B—H15B0.9500
C5B—H5B10.9900C16B—H16B0.9500
C5B—H5B20.9900C21B—C26B1.385 (6)
C6B—H6B10.9900C21B—C22B1.387 (6)
C6B—H6B20.9900C22B—C23B1.396 (6)
O1B—H1B10.8400C22B—H22B0.9500
O2B—H2B10.8400C23B—C24B1.390 (6)
C1B'—O1B'1.439 (7)C23B—H23B0.9500
C1B'—C6B'1.510 (9)C24B—C25B1.376 (7)
C1B'—C2B'1.513 (7)C24B—H24B0.9500
C1B'—H1B'1.0000C25B—C26B1.382 (5)
C2B'—O2B'1.431 (8)C25B—H25B0.9500
C2B'—C3B'1.516 (7)C26B—H26B0.9500
C2B'—H2B'1.0000C31B—C32B1.388 (6)
C3B'—C4B'1.521 (9)C31B—C36B1.390 (6)
C3B'—H3B30.9900C32B—C33B1.389 (6)
C3B'—H3B40.9900C32B—H32B0.9500
C4B'—C5B'1.515 (7)C33B—C34B1.386 (6)
C4B'—H4B30.9900C33B—H33B0.9500
C4B'—H4B40.9900C34B—C35B1.384 (7)
C5B'—C6B'1.515 (7)C34B—H34B0.9500
C5B'—H5B30.9900C35B—C36B1.379 (6)
C5B'—H5B40.9900C35B—H35B0.9500
C6B'—H6B30.9900C36B—H36B0.9500
O1A—C1A—C2A107.8 (4)C6B'—C5B'—C4B'110.9 (8)
O1A—C1A—C6A112.2 (5)C6B'—C5B'—H5B3109.5
C2A—C1A—C6A111.2 (4)C4B'—C5B'—H5B3109.5
O1A—C1A—H1A108.5C6B'—C5B'—H5B4109.5
C2A—C1A—H1A108.5C4B'—C5B'—H5B4109.5
C6A—C1A—H1A108.5H5B3—C5B'—H5B4108.1
O2A—C2A—C1A110.3 (4)C1B'—C6B'—C5B'111.8 (8)
O2A—C2A—C3A108.8 (4)C1B'—C6B'—H6B3109.3
C1A—C2A—C3A111.2 (4)C5B'—C6B'—H6B3109.3
O2A—C2A—H2A108.8C1B'—C6B'—H6B4109.3
C1A—C2A—H2A108.8C5B'—C6B'—H6B4109.3
C3A—C2A—H2A108.8H6B3—C6B'—H6B4107.9
C2A—C3A—C4A110.4 (4)C1B'—O1B'—H1B2109.5
C2A—C3A—H3A1109.6C2B'—O2B'—H2B2109.5
C4A—C3A—H3A1109.6O11A—P01A—C31A111.85 (18)
C2A—C3A—H3A2109.6O11A—P01A—C21A113.88 (16)
C4A—C3A—H3A2109.6C31A—P01A—C21A106.46 (17)
H3A1—C3A—H3A2108.1O11A—P01A—C11A111.53 (16)
C5A—C4A—C3A111.1 (5)C31A—P01A—C11A106.63 (17)
C5A—C4A—H4A1109.4C21A—P01A—C11A105.99 (17)
C3A—C4A—H4A1109.4C12A—C11A—C16A120.2 (3)
C5A—C4A—H4A2109.4C12A—C11A—P01A117.2 (3)
C3A—C4A—H4A2109.4C16A—C11A—P01A122.6 (3)
H4A1—C4A—H4A2108.0C13A—C12A—C11A120.5 (4)
C6A—C5A—C4A111.6 (5)C13A—C12A—H12A119.8
C6A—C5A—H5A1109.3C11A—C12A—H12A119.8
C4A—C5A—H5A1109.3C12A—C13A—C14A119.5 (4)
C6A—C5A—H5A2109.3C12A—C13A—H13A120.2
C4A—C5A—H5A2109.3C14A—C13A—H13A120.2
H5A1—C5A—H5A2108.0C15A—C14A—C13A120.2 (4)
C5A—C6A—C1A111.2 (5)C15A—C14A—H14A119.9
C5A—C6A—H6A1109.4C13A—C14A—H14A119.9
C1A—C6A—H6A1109.4C14A—C15A—C16A120.7 (4)
C5A—C6A—H6A2109.4C14A—C15A—H15A119.7
C1A—C6A—H6A2109.4C16A—C15A—H15A119.7
H6A1—C6A—H6A2108.0C15A—C16A—C11A118.9 (3)
O1A'—C1A'—C2A'109.3 (7)C15A—C16A—H16A120.5
O1A'—C1A'—C6A'110.6 (7)C11A—C16A—H16A120.5
C2A'—C1A'—C6A'110.7 (7)C26A—C21A—C22A119.2 (3)
O1A'—C1A'—H1A'108.8C26A—C21A—P01A122.5 (3)
C2A'—C1A'—H1A'108.8C22A—C21A—P01A118.2 (3)
C6A'—C1A'—H1A'108.8C23A—C22A—C21A120.6 (4)
O2A'—C2A'—C1A'110.0 (7)C23A—C22A—H22A119.7
O2A'—C2A'—C3A'108.5 (7)C21A—C22A—H22A119.7
C1A'—C2A'—C3A'110.8 (6)C22A—C23A—C24A120.7 (4)
O2A'—C2A'—H2A'109.2C22A—C23A—H23A119.7
C1A'—C2A'—H2A'109.2C24A—C23A—H23A119.7
C3A'—C2A'—H2A'109.2C25A—C24A—C23A119.4 (4)
C2A'—C3A'—C4A'110.2 (7)C25A—C24A—H24A120.3
C2A'—C3A'—H3A3109.6C23A—C24A—H24A120.3
C4A'—C3A'—H3A3109.6C24A—C25A—C26A121.0 (4)
C2A'—C3A'—H3A4109.6C24A—C25A—H25A119.5
C4A'—C3A'—H3A4109.6C26A—C25A—H25A119.5
H3A3—C3A'—H3A4108.1C21A—C26A—C25A119.1 (4)
C5A'—C4A'—C3A'109.7 (8)C21A—C26A—H26A120.4
C5A'—C4A'—H4A3109.7C25A—C26A—H26A120.4
C3A'—C4A'—H4A3109.7C36A—C31A—C32A119.4 (4)
C5A'—C4A'—H4A4109.7C36A—C31A—P01A123.0 (3)
C3A'—C4A'—H4A4109.7C32A—C31A—P01A117.6 (3)
H4A3—C4A'—H4A4108.2C33A—C32A—C31A119.7 (4)
C6A'—C5A'—C4A'110.8 (7)C33A—C32A—H32A120.1
C6A'—C5A'—H5A3109.5C31A—C32A—H32A120.1
C4A'—C5A'—H5A3109.5C34A—C33A—C32A120.5 (4)
C6A'—C5A'—H5A4109.5C34A—C33A—H33A119.8
C4A'—C5A'—H5A4109.5C32A—C33A—H33A119.8
H5A3—C5A'—H5A4108.1C33A—C34A—C35A120.3 (4)
C5A'—C6A'—C1A'111.0 (8)C33A—C34A—H34A119.9
C5A'—C6A'—H6A3109.4C35A—C34A—H34A119.9
C1A'—C6A'—H6A3109.4C34A—C35A—C36A119.7 (4)
C5A'—C6A'—H6A4109.4C34A—C35A—H35A120.1
C1A'—C6A'—H6A4109.4C36A—C35A—H35A120.1
H6A3—C6A'—H6A4108.0C31A—C36A—C35A120.3 (4)
C1A'—O1A'—H1A2109.5C31A—C36A—H36A119.8
C2A'—O2A'—H2A2109.5C35A—C36A—H36A119.8
O1B—C1B—C6B109.1 (4)O11B—P01B—C21B114.21 (16)
O1B—C1B—C2B111.0 (4)O11B—P01B—C11B111.85 (17)
C6B—C1B—C2B111.3 (4)C21B—P01B—C11B105.72 (17)
O1B—C1B—H1B108.4O11B—P01B—C31B111.47 (18)
C6B—C1B—H1B108.4C21B—P01B—C31B106.52 (17)
C2B—C1B—H1B108.4C11B—P01B—C31B106.57 (17)
O2B—C2B—C1B107.5 (4)C16B—C11B—C12B119.1 (3)
O2B—C2B—C3B112.5 (5)C16B—C11B—P01B123.5 (3)
C1B—C2B—C3B110.3 (4)C12B—C11B—P01B117.4 (3)
O2B—C2B—H2B108.8C13B—C12B—C11B120.4 (4)
C1B—C2B—H2B108.8C13B—C12B—H12B119.8
C3B—C2B—H2B108.8C11B—C12B—H12B119.8
C2B—C3B—C4B110.9 (4)C14B—C13B—C12B120.1 (4)
C2B—C3B—H3B1109.5C14B—C13B—H13B119.9
C4B—C3B—H3B1109.5C12B—C13B—H13B119.9
C2B—C3B—H3B2109.5C13B—C14B—C15B120.3 (4)
C4B—C3B—H3B2109.5C13B—C14B—H14B119.9
H3B1—C3B—H3B2108.0C15B—C14B—H14B119.9
C5B—C4B—C3B111.7 (5)C14B—C15B—C16B119.9 (4)
C5B—C4B—H4B1109.3C14B—C15B—H15B120.0
C3B—C4B—H4B1109.3C16B—C15B—H15B120.0
C5B—C4B—H4B2109.3C11B—C16B—C15B120.1 (4)
C3B—C4B—H4B2109.3C11B—C16B—H16B120.0
H4B1—C4B—H4B2107.9C15B—C16B—H16B120.0
C6B—C5B—C4B111.1 (4)C26B—C21B—C22B118.5 (3)
C6B—C5B—H5B1109.4C26B—C21B—P01B123.2 (3)
C4B—C5B—H5B1109.4C22B—C21B—P01B118.1 (3)
C6B—C5B—H5B2109.4C21B—C22B—C23B120.5 (4)
C4B—C5B—H5B2109.4C21B—C22B—H22B119.8
H5B1—C5B—H5B2108.0C23B—C22B—H22B119.8
C1B—C6B—C5B112.8 (4)C24B—C23B—C22B119.8 (4)
C1B—C6B—H6B1109.0C24B—C23B—H23B120.1
C5B—C6B—H6B1109.0C22B—C23B—H23B120.1
C1B—C6B—H6B2109.0C25B—C24B—C23B119.8 (4)
C5B—C6B—H6B2109.0C25B—C24B—H24B120.1
H6B1—C6B—H6B2107.8C23B—C24B—H24B120.1
O1B'—C1B'—C6B'109.9 (8)C24B—C25B—C26B119.9 (4)
O1B'—C1B'—C2B'109.7 (8)C24B—C25B—H25B120.0
C6B'—C1B'—C2B'111.5 (8)C26B—C25B—H25B120.0
O1B'—C1B'—H1B'108.5C25B—C26B—C21B121.5 (4)
C6B'—C1B'—H1B'108.5C25B—C26B—H26B119.3
C2B'—C1B'—H1B'108.5C21B—C26B—H26B119.3
O2B'—C2B'—C1B'107.0 (8)C32B—C31B—C36B119.6 (4)
O2B'—C2B'—C3B'111.4 (9)C32B—C31B—P01B117.6 (3)
C1B'—C2B'—C3B'110.6 (7)C36B—C31B—P01B122.8 (3)
O2B'—C2B'—H2B'109.3C31B—C32B—C33B120.0 (3)
C1B'—C2B'—H2B'109.3C31B—C32B—H32B120.0
C3B'—C2B'—H2B'109.3C33B—C32B—H32B120.0
C2B'—C3B'—C4B'112.1 (9)C34B—C33B—C32B120.2 (4)
C2B'—C3B'—H3B3109.2C34B—C33B—H33B119.9
C4B'—C3B'—H3B3109.2C32B—C33B—H33B119.9
C2B'—C3B'—H3B4109.2C35B—C34B—C33B119.6 (4)
C4B'—C3B'—H3B4109.2C35B—C34B—H34B120.2
H3B3—C3B'—H3B4107.9C33B—C34B—H34B120.2
C5B'—C4B'—C3B'112.0 (9)C36B—C35B—C34B120.5 (4)
C5B'—C4B'—H4B3109.2C36B—C35B—H35B119.8
C3B'—C4B'—H4B3109.2C34B—C35B—H35B119.8
C5B'—C4B'—H4B4109.2C35B—C36B—C31B120.1 (4)
C3B'—C4B'—H4B4109.2C35B—C36B—H36B119.9
H4B3—C4B'—H4B4107.9C31B—C36B—H36B119.9
O1A—C1A—C2A—O2A59.4 (7)C26A—C21A—C22A—C23A2.1 (6)
C6A—C1A—C2A—O2A177.3 (5)P01A—C21A—C22A—C23A175.7 (3)
O1A—C1A—C2A—C3A179.8 (4)C21A—C22A—C23A—C24A0.8 (6)
C6A—C1A—C2A—C3A56.5 (7)C22A—C23A—C24A—C25A0.7 (6)
O2A—C2A—C3A—C4A178.2 (5)C23A—C24A—C25A—C26A0.9 (6)
C1A—C2A—C3A—C4A56.5 (7)C22A—C21A—C26A—C25A1.8 (6)
C2A—C3A—C4A—C5A55.8 (9)P01A—C21A—C26A—C25A175.8 (3)
C3A—C4A—C5A—C6A55.3 (10)C24A—C25A—C26A—C21A0.4 (6)
C4A—C5A—C6A—C1A54.8 (10)O11A—P01A—C31A—C36A158.9 (3)
O1A—C1A—C6A—C5A176.0 (5)C21A—P01A—C31A—C36A76.1 (3)
C2A—C1A—C6A—C5A55.2 (9)C11A—P01A—C31A—C36A36.7 (4)
O1A'—C1A'—C2A'—O2A'61.5 (11)O11A—P01A—C31A—C32A20.4 (3)
C6A'—C1A'—C2A'—O2A'176.5 (11)C21A—P01A—C31A—C32A104.6 (3)
O1A'—C1A'—C2A'—C3A'178.6 (9)C11A—P01A—C31A—C32A142.6 (3)
C6A'—C1A'—C2A'—C3A'56.6 (12)C36A—C31A—C32A—C33A1.1 (5)
O2A'—C2A'—C3A'—C4A'178.9 (11)P01A—C31A—C32A—C33A178.2 (3)
C1A'—C2A'—C3A'—C4A'58.0 (12)C31A—C32A—C33A—C34A0.1 (5)
C2A'—C3A'—C4A'—C5A'58.3 (16)C32A—C33A—C34A—C35A1.5 (6)
C3A'—C4A'—C5A'—C6A'58.0 (15)C33A—C34A—C35A—C36A1.6 (6)
C4A'—C5A'—C6A'—C1A'57.0 (16)C32A—C31A—C36A—C35A1.1 (6)
O1A'—C1A'—C6A'—C5A'177.2 (12)P01A—C31A—C36A—C35A178.3 (3)
C2A'—C1A'—C6A'—C5A'56.0 (17)C34A—C35A—C36A—C31A0.3 (6)
O1B—C1B—C2B—O2B58.6 (7)O11B—P01B—C11B—C16B158.7 (3)
C6B—C1B—C2B—O2B179.6 (5)C21B—P01B—C11B—C16B33.9 (4)
O1B—C1B—C2B—C3B178.4 (4)C31B—P01B—C11B—C16B79.2 (3)
C6B—C1B—C2B—C3B56.6 (7)O11B—P01B—C11B—C12B22.1 (3)
O2B—C2B—C3B—C4B177.5 (5)C21B—P01B—C11B—C12B147.0 (3)
C1B—C2B—C3B—C4B57.5 (8)C31B—P01B—C11B—C12B99.9 (3)
C2B—C3B—C4B—C5B56.1 (9)C16B—C11B—C12B—C13B0.8 (6)
C3B—C4B—C5B—C6B52.8 (9)P01B—C11B—C12B—C13B178.4 (3)
O1B—C1B—C6B—C5B177.5 (5)C11B—C12B—C13B—C14B0.8 (6)
C2B—C1B—C6B—C5B54.7 (8)C12B—C13B—C14B—C15B1.7 (6)
C4B—C5B—C6B—C1B52.3 (9)C13B—C14B—C15B—C16B1.0 (6)
O1B'—C1B'—C2B'—O2B'60.9 (14)C12B—C11B—C16B—C15B1.5 (5)
C6B'—C1B'—C2B'—O2B'177.0 (15)P01B—C11B—C16B—C15B177.7 (3)
O1B'—C1B'—C2B'—C3B'177.7 (11)C14B—C15B—C16B—C11B0.6 (6)
C6B'—C1B'—C2B'—C3B'55.6 (14)O11B—P01B—C21B—C26B113.7 (3)
O2B'—C2B'—C3B'—C4B'173.1 (17)C11B—P01B—C21B—C26B122.9 (3)
C1B'—C2B'—C3B'—C4B'54.3 (17)C31B—P01B—C21B—C26B9.8 (4)
C2B'—C3B'—C4B'—C5B'54 (2)O11B—P01B—C21B—C22B61.9 (4)
C3B'—C4B'—C5B'—C6B'53.3 (19)C11B—P01B—C21B—C22B61.5 (3)
O1B'—C1B'—C6B'—C5B'178.4 (14)C31B—P01B—C21B—C22B174.6 (3)
C2B'—C1B'—C6B'—C5B'56.5 (19)C26B—C21B—C22B—C23B0.8 (6)
C4B'—C5B'—C6B'—C1B'54.8 (18)P01B—C21B—C22B—C23B176.6 (3)
O11A—P01A—C11A—C12A23.3 (4)C21B—C22B—C23B—C24B1.8 (7)
C31A—P01A—C11A—C12A99.1 (3)C22B—C23B—C24B—C25B1.8 (7)
C21A—P01A—C11A—C12A147.8 (3)C23B—C24B—C25B—C26B0.9 (6)
O11A—P01A—C11A—C16A158.5 (3)C24B—C25B—C26B—C21B0.1 (6)
C31A—P01A—C11A—C16A79.1 (3)C22B—C21B—C26B—C25B0.2 (6)
C21A—P01A—C11A—C16A34.0 (4)P01B—C21B—C26B—C25B175.5 (3)
C16A—C11A—C12A—C13A0.4 (6)O11B—P01B—C31B—C32B22.3 (3)
P01A—C11A—C12A—C13A177.8 (3)C21B—P01B—C31B—C32B102.9 (3)
C11A—C12A—C13A—C14A1.0 (6)C11B—P01B—C31B—C32B144.6 (3)
C12A—C13A—C14A—C15A1.4 (6)O11B—P01B—C31B—C36B158.2 (3)
C13A—C14A—C15A—C16A0.2 (7)C21B—P01B—C31B—C36B76.6 (3)
C14A—C15A—C16A—C11A1.3 (6)C11B—P01B—C31B—C36B35.9 (4)
C12A—C11A—C16A—C15A1.6 (6)C36B—C31B—C32B—C33B1.6 (5)
P01A—C11A—C16A—C15A176.6 (3)P01B—C31B—C32B—C33B178.9 (3)
O11A—P01A—C21A—C26A114.7 (3)C31B—C32B—C33B—C34B0.7 (5)
C31A—P01A—C21A—C26A9.1 (4)C32B—C33B—C34B—C35B0.7 (6)
C11A—P01A—C21A—C26A122.3 (3)C33B—C34B—C35B—C36B1.3 (6)
O11A—P01A—C21A—C22A63.0 (3)C34B—C35B—C36B—C31B0.5 (6)
C31A—P01A—C21A—C22A173.3 (3)C32B—C31B—C36B—C35B1.0 (5)
C11A—P01A—C21A—C22A60.0 (3)P01B—C31B—C36B—C35B179.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A1···O1Bi0.841.922.763 (7)176
O2A—H2A1···O1Aii0.841.892.718 (6)166
O1B—H1B1···O2Bi0.841.942.750 (7)160
O2B—H2B1···O2Aii0.841.912.748 (8)176
O1A—H1A2···O2Aii0.841.992.778 (16)156
O2A—H2A2···O2Bii0.842.302.72 (2)111
O1B—H1B2···O1Ai0.841.942.752 (19)162
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.
(acetone90Kmono) 1:1 rac-1,2-cyclohexanediol triphenylphosphine oxide top
Crystal data top
C6H12O2·C18H15OPF(000) = 1680
Mr = 394.43Dx = 1.270 Mg m3
Monoclinic, C12/c1Mo Kα radiation, λ = 0.71073 Å
a = 41.501 (4) ÅCell parameters from 9276 reflections
b = 9.276 (1) Åθ = 1.0–27.5°
c = 10.913 (1) ŵ = 0.16 mm1
β = 100.96 (1)°T = 90 K
V = 4124.5 (7) Å3Lath, colorless
Z = 80.25 × 0.21 × 0.13 mm
Data collection top
Nonius KappaCCD
diffractometer
3630 independent reflections
Radiation source: fine-focus sealed tube2713 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.179
Detector resolution: 10 pixels mm-1θmax = 25.0°, θmin = 1.0°
1.0° ω scans at fixed χ = 55°h = 4949
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
k = 1111
Tmin = 0.96, Tmax = 0.98l = 1212
13911 measured 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)] = 0.074Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H-atom parameters constrained
S = 1.28 w = 1/[σ2(Fo2) + (0.P)2 + 4.778P]
where P = (Fo2 + 2Fc2)/3
3630 reflections(Δ/σ)max = 0.001
282 parametersΔρmax = 0.31 e Å3
68 restraintsΔρmin = 0.30 e Å3
Crystal data top
C6H12O2·C18H15OPV = 4124.5 (7) Å3
Mr = 394.43Z = 8
Monoclinic, C12/c1Mo Kα radiation
a = 41.501 (4) ŵ = 0.16 mm1
b = 9.276 (1) ÅT = 90 K
c = 10.913 (1) Å0.25 × 0.21 × 0.13 mm
β = 100.96 (1)°
Data collection top
Nonius KappaCCD
diffractometer
3630 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
2713 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.98Rint = 0.179
13911 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.07468 restraints
wR(F2) = 0.121H-atom parameters constrained
S = 1.28Δρmax = 0.31 e Å3
3630 reflectionsΔρmin = 0.30 e Å3
282 parameters
Special details top

Experimental. The crystal-to-detector distance was 40 mm. Each frame was measured for 20 s. The number of scan sets measured was 9; the total number of frames measured was 951.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.0190 (3)0.7574 (12)0.0771 (9)0.022 (2)0.478 (6)
H10.00060.82840.05860.027*0.478 (6)
C20.0289 (3)0.7196 (13)0.0452 (10)0.026 (3)0.478 (6)
H20.04660.64520.02830.032*0.478 (6)
C30.0423 (3)0.8493 (10)0.1039 (10)0.029 (2)0.478 (6)
H3A0.02430.91920.13130.035*0.478 (6)
H3B0.05080.81800.17840.035*0.478 (6)
C40.0696 (6)0.922 (3)0.0126 (13)0.036 (2)0.478 (6)
H4A0.08890.85780.00360.043*0.478 (6)
H4B0.07611.01180.05100.043*0.478 (6)
C50.0598 (2)0.9596 (10)0.1104 (9)0.0313 (15)0.478 (6)
H5A0.04281.03600.09670.038*0.478 (6)
H5B0.07910.99750.16910.038*0.478 (6)
C60.0464 (5)0.828 (2)0.1677 (13)0.028 (3)0.478 (6)
H6A0.06430.75710.19290.034*0.478 (6)
H6B0.03820.85690.24350.034*0.478 (6)
O10.0064 (3)0.6299 (11)0.1252 (12)0.0290 (16)0.478 (6)
H010.01030.60160.07500.043*0.478 (6)
O20.0017 (4)0.6596 (13)0.1328 (16)0.0251 (19)0.478 (6)
H020.00760.64400.20110.038*0.478 (6)
C1'0.0267 (3)0.7174 (10)0.0879 (8)0.022 (2)0.522 (6)
H1'0.04320.63760.10460.027*0.522 (6)
C2'0.0201 (3)0.7527 (12)0.0500 (9)0.026 (3)0.522 (6)
H2'0.00290.82950.06840.032*0.522 (6)
C3'0.0517 (2)0.8034 (10)0.0876 (10)0.029 (2)0.522 (6)
H3'A0.04740.82620.17780.035*0.522 (6)
H3'B0.06820.72520.07250.035*0.522 (6)
C4'0.0651 (6)0.937 (2)0.0134 (11)0.036 (2)0.522 (6)
H4'A0.04931.01710.03320.043*0.522 (6)
H4'B0.08600.96620.03730.043*0.522 (6)
C5'0.0710 (2)0.9055 (10)0.1264 (8)0.0313 (15)0.522 (6)
H5'A0.07800.99500.17330.038*0.522 (6)
H5'B0.08880.83360.14780.038*0.522 (6)
C6'0.0398 (4)0.848 (2)0.1646 (12)0.028 (3)0.522 (6)
H6'A0.04460.82110.25410.034*0.522 (6)
H6'B0.02280.92420.15310.034*0.522 (6)
O1'0.0032 (2)0.6733 (9)0.1275 (11)0.0290 (16)0.522 (6)
H01'0.00140.64220.20110.043*0.522 (6)
O2'0.0084 (3)0.6215 (12)0.1153 (14)0.0251 (19)0.522 (6)
H02'0.01110.60620.10830.038*0.522 (6)
P10.16781 (2)0.61898 (10)0.16242 (8)0.0200 (2)
O110.17068 (5)0.6726 (2)0.29227 (18)0.0234 (5)
C110.13362 (7)0.4965 (3)0.1199 (3)0.0192 (7)
C120.10829 (7)0.5065 (3)0.1875 (3)0.0226 (7)
H120.10980.57360.25420.027*
C130.08098 (8)0.4187 (4)0.1573 (3)0.0305 (9)
H130.06390.42500.20390.037*
C140.07843 (8)0.3224 (4)0.0602 (3)0.0323 (9)
H140.05940.26380.03900.039*
C150.10362 (8)0.3107 (4)0.0069 (3)0.0287 (8)
H150.10190.24370.07360.034*
C160.13141 (8)0.3972 (4)0.0237 (3)0.0224 (7)
H160.14880.38820.02120.027*
C210.20346 (7)0.5226 (4)0.1351 (3)0.0212 (7)
C220.21185 (8)0.3952 (4)0.2015 (3)0.0308 (8)
H220.19820.35900.25520.037*
C230.24024 (8)0.3212 (4)0.1890 (3)0.0368 (9)
H230.24590.23440.23420.044*
C240.26019 (8)0.3735 (4)0.1111 (3)0.0323 (9)
H240.27970.32340.10360.039*
C250.25175 (8)0.4983 (4)0.0444 (3)0.0322 (9)
H250.26530.53390.00970.039*
C260.22335 (8)0.5723 (4)0.0561 (3)0.0283 (8)
H260.21760.65790.00930.034*
C310.16111 (8)0.7648 (3)0.0499 (3)0.0214 (7)
C320.17026 (7)0.9028 (4)0.0927 (3)0.0225 (8)
H320.18020.91710.17770.027*
C330.16500 (8)1.0196 (4)0.0123 (3)0.0291 (8)
H330.17091.11390.04250.035*
C340.15116 (8)0.9986 (4)0.1124 (3)0.0286 (8)
H340.14761.07850.16780.034*
C350.14258 (8)0.8613 (4)0.1560 (3)0.0301 (8)
H350.13330.84680.24170.036*
C360.14746 (8)0.7452 (4)0.0752 (3)0.0266 (8)
H360.14140.65110.10570.032*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.023 (5)0.017 (5)0.026 (2)0.002 (4)0.004 (3)0.002 (3)
C20.032 (5)0.020 (5)0.0266 (18)0.006 (4)0.006 (3)0.003 (2)
C30.035 (5)0.022 (5)0.032 (3)0.004 (4)0.010 (3)0.001 (3)
C40.036 (5)0.031 (4)0.043 (2)0.010 (4)0.015 (2)0.0049 (19)
C50.029 (4)0.022 (5)0.040 (3)0.004 (3)0.001 (3)0.006 (3)
C60.033 (6)0.025 (4)0.0260 (19)0.003 (5)0.001 (3)0.003 (2)
O10.041 (5)0.022 (5)0.0263 (15)0.010 (3)0.011 (3)0.003 (3)
O20.031 (5)0.017 (5)0.026 (4)0.000 (3)0.000 (3)0.000 (4)
C1'0.023 (5)0.017 (5)0.026 (2)0.002 (4)0.004 (3)0.002 (3)
C2'0.032 (5)0.020 (5)0.0266 (18)0.006 (4)0.006 (3)0.003 (2)
C3'0.035 (5)0.022 (5)0.032 (3)0.004 (4)0.010 (3)0.001 (3)
C4'0.036 (5)0.031 (4)0.043 (2)0.010 (4)0.015 (2)0.0049 (19)
C5'0.029 (4)0.022 (5)0.040 (3)0.004 (3)0.001 (3)0.006 (3)
C6'0.033 (6)0.025 (4)0.0260 (19)0.003 (5)0.001 (3)0.003 (2)
O1'0.041 (5)0.022 (5)0.0263 (15)0.010 (3)0.011 (3)0.003 (3)
O2'0.031 (5)0.017 (5)0.026 (4)0.000 (3)0.000 (3)0.000 (4)
P10.0209 (4)0.0170 (4)0.0221 (4)0.0005 (4)0.0042 (3)0.0000 (4)
O110.0264 (12)0.0243 (13)0.0200 (11)0.0008 (10)0.0055 (9)0.0000 (10)
C110.0173 (16)0.0152 (17)0.0237 (17)0.0025 (13)0.0002 (13)0.0043 (14)
C120.0227 (17)0.0185 (18)0.0270 (18)0.0038 (14)0.0057 (14)0.0002 (15)
C130.0213 (18)0.030 (2)0.041 (2)0.0026 (15)0.0062 (16)0.0020 (17)
C140.0210 (18)0.025 (2)0.048 (2)0.0036 (15)0.0011 (16)0.0097 (18)
C150.033 (2)0.0187 (18)0.0311 (19)0.0002 (16)0.0012 (16)0.0019 (16)
C160.0234 (17)0.0174 (17)0.0259 (17)0.0023 (14)0.0035 (14)0.0038 (15)
C210.0156 (16)0.0217 (18)0.0250 (17)0.0042 (14)0.0010 (13)0.0058 (15)
C220.0295 (19)0.034 (2)0.0288 (18)0.0027 (17)0.0068 (15)0.0073 (18)
C230.035 (2)0.035 (2)0.037 (2)0.0127 (18)0.0011 (17)0.0051 (19)
C240.0218 (18)0.038 (2)0.035 (2)0.0072 (17)0.0006 (15)0.0101 (19)
C250.0268 (19)0.033 (2)0.039 (2)0.0005 (17)0.0109 (17)0.0016 (18)
C260.0287 (19)0.023 (2)0.033 (2)0.0011 (15)0.0073 (16)0.0012 (15)
C310.0190 (17)0.0188 (18)0.0267 (18)0.0008 (14)0.0046 (14)0.0022 (15)
C320.0206 (17)0.0216 (19)0.0267 (18)0.0001 (14)0.0080 (14)0.0006 (15)
C330.0269 (19)0.0174 (18)0.046 (2)0.0002 (15)0.0142 (17)0.0014 (17)
C340.031 (2)0.022 (2)0.035 (2)0.0052 (16)0.0115 (16)0.0108 (16)
C350.031 (2)0.030 (2)0.0287 (19)0.0035 (17)0.0056 (16)0.0048 (17)
C360.033 (2)0.0173 (18)0.0299 (19)0.0017 (15)0.0069 (16)0.0005 (15)
Geometric parameters (Å, º) top
C1—O11.432 (17)O2'—H02'0.8400
C1—C61.506 (13)P1—O111.485 (2)
C1—C21.510 (11)P1—C211.801 (3)
C1—H11.0000P1—C111.808 (3)
C2—O21.44 (2)P1—C311.813 (3)
C2—C31.517 (11)C11—C161.387 (4)
C2—H21.0000C11—C121.397 (4)
C3—C41.520 (13)C12—C131.384 (4)
C3—H3A0.9900C12—H120.9500
C3—H3B0.9900C13—C141.374 (5)
C4—C51.516 (13)C13—H130.9500
C4—H4A0.9900C14—C151.390 (5)
C4—H4B0.9900C14—H140.9500
C5—C61.527 (13)C15—C161.392 (4)
C5—H5A0.9900C15—H150.9500
C5—H5B0.9900C16—H160.9500
C6—H6A0.9900C21—C261.381 (4)
C6—H6B0.9900C21—C221.396 (5)
O1—H010.8400C22—C231.393 (5)
O2—H020.8400C22—H220.9500
C1'—O1'1.448 (16)C23—C241.383 (5)
C1'—C6'1.511 (12)C23—H230.9500
C1'—C2'1.513 (11)C24—C251.377 (5)
C1'—H1'1.0000C24—H240.9500
C2'—O2'1.447 (19)C25—C261.390 (5)
C2'—C3'1.523 (10)C25—H250.9500
C2'—H2'1.0000C26—H260.9500
C3'—C4'1.524 (13)C31—C361.387 (4)
C3'—H3'A0.9900C31—C321.391 (5)
C3'—H3'B0.9900C32—C331.386 (5)
C4'—C5'1.525 (13)C32—H320.9500
C4'—H4'A0.9900C33—C341.386 (5)
C4'—H4'B0.9900C33—H330.9500
C5'—C6'1.532 (12)C34—C351.382 (5)
C5'—H5'A0.9900C34—H340.9500
C5'—H5'B0.9900C35—C361.383 (5)
C6'—H6'A0.9900C35—H350.9500
C6'—H6'B0.9900C36—H360.9500
O1'—H01'0.8400
O1—C1—C6113.5 (10)C1'—C6'—H6'A109.4
O1—C1—C2108.2 (9)C5'—C6'—H6'A109.4
C6—C1—C2112.5 (11)C1'—C6'—H6'B109.4
O1—C1—H1107.5C5'—C6'—H6'B109.4
C6—C1—H1107.5H6'A—C6'—H6'B108.0
C2—C1—H1107.5C1'—O1'—H01'109.5
O2—C2—C1111.5 (11)C2'—O2'—H02'109.5
O2—C2—C3109.2 (11)O11—P1—C21113.88 (13)
C1—C2—C3111.9 (9)O11—P1—C11111.83 (13)
O2—C2—H2108.1C21—P1—C11105.97 (15)
C1—C2—H2108.1O11—P1—C31111.74 (14)
C3—C2—H2108.1C21—P1—C31106.45 (15)
C2—C3—C4111.4 (11)C11—P1—C31106.46 (14)
C2—C3—H3A109.3C16—C11—C12119.7 (3)
C4—C3—H3A109.3C16—C11—P1123.2 (2)
C2—C3—H3B109.3C12—C11—P1117.1 (2)
C4—C3—H3B109.3C13—C12—C11120.0 (3)
H3A—C3—H3B108.0C13—C12—H12120.0
C5—C4—C3112.9 (13)C11—C12—H12120.0
C5—C4—H4A109.0C14—C13—C12120.4 (3)
C3—C4—H4A109.0C14—C13—H13119.8
C5—C4—H4B109.0C12—C13—H13119.8
C3—C4—H4B109.0C13—C14—C15120.1 (3)
H4A—C4—H4B107.8C13—C14—H14119.9
C4—C5—C6111.1 (11)C15—C14—H14119.9
C4—C5—H5A109.4C14—C15—C16120.0 (3)
C6—C5—H5A109.4C14—C15—H15120.0
C4—C5—H5B109.4C16—C15—H15120.0
C6—C5—H5B109.4C11—C16—C15119.8 (3)
H5A—C5—H5B108.0C11—C16—H16120.1
C1—C6—C5111.5 (12)C15—C16—H16120.1
C1—C6—H6A109.3C26—C21—C22119.1 (3)
C5—C6—H6A109.3C26—C21—P1123.0 (3)
C1—C6—H6B109.3C22—C21—P1117.8 (3)
C5—C6—H6B109.3C23—C22—C21120.0 (3)
H6A—C6—H6B108.0C23—C22—H22120.0
O1'—C1'—C6'107.4 (9)C21—C22—H22120.0
O1'—C1'—C2'110.7 (9)C24—C23—C22120.2 (4)
C6'—C1'—C2'110.8 (10)C24—C23—H23119.9
O1'—C1'—H1'109.3C22—C23—H23119.9
C6'—C1'—H1'109.3C25—C24—C23119.9 (3)
C2'—C1'—H1'109.3C25—C24—H24120.1
O2'—C2'—C1'106.8 (10)C23—C24—H24120.1
O2'—C2'—C3'110.5 (10)C24—C25—C26120.1 (3)
C1'—C2'—C3'109.4 (9)C24—C25—H25119.9
O2'—C2'—H2'110.0C26—C25—H25119.9
C1'—C2'—H2'110.0C21—C26—C25120.7 (3)
C3'—C2'—H2'110.0C21—C26—H26119.7
C2'—C3'—C4'110.8 (10)C25—C26—H26119.7
C2'—C3'—H3'A109.5C36—C31—C32119.1 (3)
C4'—C3'—H3'A109.5C36—C31—P1123.4 (3)
C2'—C3'—H3'B109.5C32—C31—P1117.6 (2)
C4'—C3'—H3'B109.5C33—C32—C31120.5 (3)
H3'A—C3'—H3'B108.1C33—C32—H32119.8
C3'—C4'—C5'110.5 (12)C31—C32—H32119.8
C3'—C4'—H4'A109.5C32—C33—C34119.9 (3)
C5'—C4'—H4'A109.5C32—C33—H33120.1
C3'—C4'—H4'B109.5C34—C33—H33120.1
C5'—C4'—H4'B109.5C35—C34—C33120.0 (3)
H4'A—C4'—H4'B108.1C35—C34—H34120.0
C4'—C5'—C6'110.8 (10)C33—C34—H34120.0
C4'—C5'—H5'A109.5C34—C35—C36120.1 (3)
C6'—C5'—H5'A109.5C34—C35—H35120.0
C4'—C5'—H5'B109.5C36—C35—H35120.0
C6'—C5'—H5'B109.5C35—C36—C31120.5 (3)
H5'A—C5'—H5'B108.1C35—C36—H36119.7
C1'—C6'—C5'111.3 (11)C31—C36—H36119.7
O1—C1—C2—O256.9 (14)C13—C14—C15—C160.4 (5)
C6—C1—C2—O2176.9 (12)C12—C11—C16—C151.6 (5)
O1—C1—C2—C3179.5 (9)P1—C11—C16—C15177.3 (2)
C6—C1—C2—C354.3 (17)C14—C15—C16—C111.0 (5)
O2—C2—C3—C4176.5 (14)O11—P1—C21—C26114.2 (3)
C1—C2—C3—C452.6 (18)C11—P1—C21—C26122.5 (3)
C2—C3—C4—C553 (2)C31—P1—C21—C269.4 (3)
C3—C4—C5—C653 (2)O11—P1—C21—C2263.0 (3)
O1—C1—C6—C5177.9 (11)C11—P1—C21—C2260.3 (3)
C2—C1—C6—C555 (2)C31—P1—C21—C22173.4 (2)
C4—C5—C6—C154 (2)C26—C21—C22—C231.0 (5)
O1'—C1'—C2'—O2'62.2 (13)P1—C21—C22—C23176.3 (3)
C6'—C1'—C2'—O2'178.7 (11)C21—C22—C23—C240.1 (5)
O1'—C1'—C2'—C3'178.1 (7)C22—C23—C24—C250.8 (5)
C6'—C1'—C2'—C3'59.1 (15)C23—C24—C25—C260.5 (5)
O2'—C2'—C3'—C4'176.7 (12)C22—C21—C26—C251.3 (5)
C1'—C2'—C3'—C4'59.4 (16)P1—C21—C26—C25175.9 (2)
C2'—C3'—C4'—C5'58 (2)C24—C25—C26—C210.5 (5)
C3'—C4'—C5'—C6'55 (2)O11—P1—C31—C36158.8 (3)
O1'—C1'—C6'—C5'178.2 (11)C21—P1—C31—C3676.3 (3)
C2'—C1'—C6'—C5'57.2 (18)C11—P1—C31—C3636.4 (3)
C4'—C5'—C6'—C1'54.7 (19)O11—P1—C31—C3221.2 (3)
O11—P1—C11—C16158.6 (2)C21—P1—C31—C32103.7 (3)
C21—P1—C11—C1634.0 (3)C11—P1—C31—C32143.6 (3)
C31—P1—C11—C1679.1 (3)C36—C31—C32—C331.8 (5)
O11—P1—C11—C1222.5 (3)P1—C31—C32—C33178.3 (2)
C21—P1—C11—C12147.2 (2)C31—C32—C33—C341.4 (5)
C31—P1—C11—C1299.8 (3)C32—C33—C34—C350.2 (5)
C16—C11—C12—C130.8 (5)C33—C34—C35—C360.7 (5)
P1—C11—C12—C13178.2 (2)C34—C35—C36—C310.3 (5)
C11—C12—C13—C140.7 (5)C32—C31—C36—C350.9 (5)
C12—C13—C14—C151.2 (5)P1—C31—C36—C35179.1 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H01···O1i0.841.882.64 (2)149
O2—H02···O1ii0.842.682.744 (14)86
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+1, z.
(ethanol90Kmono) 1:1 rac-1,2-cyclohexanediol triphenylphosphine oxide top
Crystal data top
C6H12O2·C18H15OPF(000) = 1680
Mr = 394.43Dx = 1.270 Mg m3
Monoclinic, C12/c1Mo Kα radiation, λ = 0.71073 Å
a = 41.506 (4) ÅCell parameters from 9409 reflections
b = 9.273 (1) Åθ = 1.0–27.5°
c = 10.919 (1) ŵ = 0.16 mm1
β = 100.98 (1)°T = 90 K
V = 4125.6 (7) Å3Lath, colorless
Z = 80.25 × 0.20 × 0.12 mm
Data collection top
Nonius KappaCCD
diffractometer
3631 independent reflections
Radiation source: fine-focus sealed tube2527 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.119
Detector resolution: 10 pixels mm-1θmax = 25.0°, θmin = 1.0°
1.0° ω scans at fixed χ = 55°h = 4949
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
k = 1111
Tmin = 0.96, Tmax = 0.98l = 1212
14015 measured 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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.107H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.0231P)2 + 3.4183P]
where P = (Fo2 + 2Fc2)/3
3631 reflections(Δ/σ)max < 0.001
282 parametersΔρmax = 0.25 e Å3
68 restraintsΔρmin = 0.28 e Å3
Crystal data top
C6H12O2·C18H15OPV = 4125.6 (7) Å3
Mr = 394.43Z = 8
Monoclinic, C12/c1Mo Kα radiation
a = 41.506 (4) ŵ = 0.16 mm1
b = 9.273 (1) ÅT = 90 K
c = 10.919 (1) Å0.25 × 0.20 × 0.12 mm
β = 100.98 (1)°
Data collection top
Nonius KappaCCD
diffractometer
3631 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
2527 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.98Rint = 0.119
14015 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05368 restraints
wR(F2) = 0.107H-atom parameters constrained
S = 1.11Δρmax = 0.25 e Å3
3631 reflectionsΔρmin = 0.28 e Å3
282 parameters
Special details top

Experimental. The crystal-to-detector distance was 45 mm. Each frame was measured for 15 s. The number of scan sets measured was 9 the total number of frames measured was 1008.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.0187 (2)0.7582 (9)0.0763 (8)0.0208 (15)0.492 (5)
H10.00030.82920.05760.025*0.492 (5)
C20.0288 (3)0.7186 (11)0.0449 (10)0.025 (2)0.492 (5)
H20.04890.65890.01680.030*0.492 (5)
C30.0421 (2)0.8486 (8)0.1041 (9)0.0293 (17)0.492 (5)
H3A0.02420.91910.13040.035*0.492 (5)
H3B0.05040.81780.17920.035*0.492 (5)
C40.0698 (5)0.920 (2)0.0123 (11)0.034 (2)0.492 (5)
H4A0.08880.85350.00460.041*0.492 (5)
H4B0.07681.00830.05070.041*0.492 (5)
C50.05988 (19)0.9593 (8)0.1100 (7)0.0310 (13)0.492 (5)
H5A0.04291.03560.09550.037*0.492 (5)
H5B0.07920.99750.16870.037*0.492 (5)
C60.0465 (4)0.8275 (17)0.1669 (12)0.027 (2)0.492 (5)
H6A0.06440.75640.19120.033*0.492 (5)
H6B0.03860.85650.24320.033*0.492 (5)
O10.0065 (2)0.6302 (9)0.1262 (10)0.0288 (13)0.492 (5)
H010.01020.60040.07660.043*0.492 (5)
O20.0074 (5)0.6218 (13)0.1139 (16)0.0295 (19)0.492 (5)
H020.00570.64000.19020.044*0.492 (5)
C1'0.0266 (2)0.7169 (8)0.0887 (7)0.0208 (15)0.508 (5)
H1'0.04300.63680.10570.025*0.508 (5)
C2'0.0203 (2)0.7521 (12)0.0488 (9)0.025 (2)0.508 (5)
H2'0.00640.84070.05550.030*0.508 (5)
C3'0.05160 (19)0.8033 (8)0.0871 (9)0.0293 (17)0.508 (5)
H3'A0.04720.82600.17740.035*0.508 (5)
H3'B0.06830.72560.07210.035*0.508 (5)
C4'0.0649 (5)0.9376 (19)0.0128 (10)0.034 (2)0.508 (5)
H4'A0.08560.96850.03710.041*0.508 (5)
H4'B0.04891.01740.03170.041*0.508 (5)
C5'0.07103 (17)0.9043 (8)0.1266 (7)0.0310 (13)0.508 (5)
H5'A0.08860.83120.14650.037*0.508 (5)
H5'B0.07840.99280.17440.037*0.508 (5)
C6'0.0400 (4)0.8479 (16)0.1648 (12)0.027 (2)0.508 (5)
H6'A0.04480.82190.25430.033*0.508 (5)
H6'B0.02310.92480.15300.033*0.508 (5)
O1'0.0032 (2)0.6733 (8)0.1277 (9)0.0288 (13)0.508 (5)
H01'0.00100.64920.20320.043*0.508 (5)
O2'0.0025 (4)0.6590 (13)0.1327 (15)0.0295 (19)0.508 (5)
H02'0.00390.57520.10280.044*0.508 (5)
P10.167809 (16)0.61877 (7)0.16215 (6)0.02045 (18)
O110.17067 (4)0.67236 (18)0.29200 (14)0.0237 (4)
C110.13362 (6)0.4964 (3)0.1190 (2)0.0195 (6)
C120.10835 (6)0.5064 (3)0.1870 (2)0.0228 (6)
H120.11000.57300.25400.027*
C130.08093 (6)0.4187 (3)0.1564 (3)0.0317 (7)
H130.06380.42550.20260.038*
C140.07840 (7)0.3221 (3)0.0598 (3)0.0338 (7)
H140.05940.26310.03880.041*
C150.10360 (6)0.3108 (3)0.0073 (2)0.0276 (6)
H150.10180.24420.07430.033*
C160.13144 (6)0.3964 (3)0.0232 (2)0.0231 (6)
H160.14890.38650.02120.028*
C210.20342 (6)0.5224 (3)0.1350 (2)0.0207 (6)
C220.21188 (6)0.3949 (3)0.2014 (2)0.0300 (7)
H220.19820.35840.25480.036*
C230.24020 (7)0.3215 (3)0.1892 (3)0.0360 (7)
H230.24590.23490.23460.043*
C240.26019 (6)0.3736 (3)0.1114 (2)0.0323 (7)
H240.27970.32350.10430.039*
C250.25177 (7)0.4976 (3)0.0446 (3)0.0329 (7)
H250.26540.53270.00970.040*
C260.22339 (6)0.5722 (3)0.0560 (2)0.0282 (7)
H260.21770.65790.00920.034*
C310.16123 (6)0.7647 (3)0.0503 (2)0.0224 (6)
C320.17019 (6)0.9026 (3)0.0925 (2)0.0221 (6)
H320.18000.91730.17750.026*
C330.16495 (6)1.0195 (3)0.0118 (3)0.0284 (7)
H330.17091.11380.04190.034*
C340.15104 (6)0.9985 (3)0.1122 (3)0.0284 (7)
H340.14721.07840.16750.034*
C350.14260 (6)0.8603 (3)0.1559 (3)0.0301 (7)
H350.13340.84540.24160.036*
C360.14753 (6)0.7445 (3)0.0749 (2)0.0255 (6)
H360.14150.65030.10500.031*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.016 (4)0.017 (4)0.0288 (19)0.005 (3)0.004 (2)0.005 (2)
C20.031 (5)0.019 (4)0.0267 (16)0.005 (4)0.006 (3)0.004 (2)
C30.030 (4)0.026 (4)0.033 (3)0.002 (3)0.011 (3)0.002 (3)
C40.030 (4)0.028 (4)0.0468 (18)0.009 (3)0.0155 (18)0.0044 (17)
C50.026 (4)0.024 (4)0.042 (2)0.003 (2)0.005 (3)0.005 (3)
C60.029 (5)0.024 (4)0.0268 (16)0.001 (4)0.001 (2)0.0002 (19)
O10.036 (4)0.026 (4)0.0268 (12)0.007 (2)0.010 (3)0.001 (3)
O20.042 (5)0.021 (5)0.024 (4)0.008 (4)0.002 (3)0.000 (3)
C1'0.016 (4)0.017 (4)0.0288 (19)0.005 (3)0.004 (2)0.005 (2)
C2'0.031 (5)0.019 (4)0.0267 (16)0.005 (4)0.006 (3)0.004 (2)
C3'0.030 (4)0.026 (4)0.033 (3)0.002 (3)0.011 (3)0.002 (3)
C4'0.030 (4)0.028 (4)0.0468 (18)0.009 (3)0.0155 (18)0.0044 (17)
C5'0.026 (4)0.024 (4)0.042 (2)0.003 (2)0.005 (3)0.005 (3)
C6'0.029 (5)0.024 (4)0.0268 (16)0.001 (4)0.001 (2)0.0002 (19)
O1'0.036 (4)0.026 (4)0.0268 (12)0.007 (2)0.010 (3)0.001 (3)
O2'0.042 (5)0.021 (5)0.024 (4)0.008 (4)0.002 (3)0.000 (3)
P10.0189 (4)0.0184 (4)0.0239 (4)0.0001 (3)0.0037 (3)0.0004 (3)
O110.0252 (10)0.0242 (10)0.0220 (10)0.0020 (8)0.0051 (8)0.0017 (8)
C110.0165 (13)0.0176 (14)0.0237 (14)0.0021 (11)0.0016 (11)0.0042 (12)
C120.0197 (14)0.0215 (14)0.0275 (15)0.0031 (12)0.0051 (12)0.0013 (12)
C130.0194 (15)0.0336 (18)0.0430 (18)0.0008 (12)0.0079 (13)0.0022 (14)
C140.0210 (16)0.0257 (16)0.0521 (19)0.0042 (12)0.0005 (14)0.0053 (15)
C150.0283 (16)0.0190 (14)0.0323 (16)0.0023 (12)0.0024 (13)0.0032 (12)
C160.0246 (15)0.0206 (14)0.0237 (14)0.0029 (12)0.0038 (11)0.0020 (12)
C210.0150 (13)0.0227 (15)0.0229 (14)0.0026 (11)0.0001 (11)0.0045 (12)
C220.0241 (15)0.0340 (17)0.0317 (16)0.0030 (13)0.0052 (12)0.0080 (14)
C230.0316 (17)0.0361 (17)0.0380 (17)0.0106 (14)0.0013 (14)0.0071 (14)
C240.0185 (14)0.0382 (18)0.0379 (17)0.0094 (13)0.0005 (12)0.0103 (15)
C250.0241 (16)0.0362 (18)0.0407 (18)0.0020 (14)0.0118 (14)0.0018 (15)
C260.0273 (16)0.0222 (15)0.0354 (17)0.0001 (12)0.0062 (13)0.0013 (12)
C310.0173 (14)0.0210 (14)0.0295 (15)0.0024 (11)0.0061 (11)0.0016 (12)
C320.0180 (14)0.0206 (15)0.0285 (15)0.0009 (11)0.0068 (11)0.0004 (12)
C330.0235 (15)0.0211 (15)0.0433 (18)0.0018 (12)0.0133 (13)0.0006 (13)
C340.0268 (16)0.0219 (15)0.0391 (17)0.0044 (12)0.0129 (13)0.0098 (13)
C350.0296 (16)0.0309 (17)0.0301 (15)0.0027 (13)0.0067 (13)0.0048 (13)
C360.0274 (16)0.0190 (15)0.0295 (16)0.0006 (12)0.0045 (12)0.0014 (12)
Geometric parameters (Å, º) top
C1—O11.437 (14)O2'—H02'0.8400
C1—C21.508 (10)P1—O111.4857 (17)
C1—C61.513 (11)P1—C211.799 (3)
C1—H11.0000P1—C111.808 (2)
C2—O21.38 (2)P1—C311.808 (3)
C2—C31.520 (10)C11—C161.388 (3)
C2—H21.0000C11—C121.399 (3)
C3—C41.523 (12)C12—C131.387 (3)
C3—H3A0.9900C12—H120.9500
C3—H3B0.9900C13—C141.372 (4)
C4—C51.515 (12)C13—H130.9500
C4—H4A0.9900C14—C151.391 (4)
C4—H4B0.9900C14—H140.9500
C5—C61.523 (11)C15—C161.389 (4)
C5—H5A0.9900C15—H150.9500
C5—H5B0.9900C16—H160.9500
C6—H6A0.9900C21—C261.385 (4)
C6—H6B0.9900C21—C221.396 (4)
O1—H010.8400C22—C231.386 (4)
O2—H020.8400C22—H220.9500
C1'—O1'1.441 (14)C23—C241.383 (4)
C1'—C2'1.510 (10)C23—H230.9500
C1'—C6'1.516 (11)C24—C251.371 (4)
C1'—H1'1.0000C24—H240.9500
C2'—O2'1.369 (19)C25—C261.392 (4)
C2'—C3'1.514 (10)C25—H250.9500
C2'—H2'1.0000C26—H260.9500
C3'—C4'1.531 (12)C31—C321.386 (3)
C3'—H3'A0.9900C31—C361.390 (3)
C3'—H3'B0.9900C32—C331.387 (4)
C4'—C5'1.526 (12)C32—H320.9500
C4'—H4'A0.9900C33—C341.381 (4)
C4'—H4'B0.9900C33—H330.9500
C5'—C6'1.522 (11)C34—C351.388 (4)
C5'—H5'A0.9900C34—H340.9500
C5'—H5'B0.9900C35—C361.382 (3)
C6'—H6'A0.9900C35—H350.9500
C6'—H6'B0.9900C36—H360.9500
O1'—H01'0.8400
O1—C1—C2108.0 (8)C1'—C6'—H6'A109.3
O1—C1—C6112.5 (8)C5'—C6'—H6'A109.3
C2—C1—C6111.8 (9)C1'—C6'—H6'B109.3
O1—C1—H1108.1C5'—C6'—H6'B109.3
C2—C1—H1108.1H6'A—C6'—H6'B108.0
C6—C1—H1108.1C1'—O1'—H01'109.5
O2—C2—C1112.2 (12)C2'—O2'—H02'109.5
O2—C2—C3122.1 (10)O11—P1—C21113.84 (11)
C1—C2—C3111.4 (8)O11—P1—C11111.99 (11)
O2—C2—H2102.8C21—P1—C11105.92 (11)
C1—C2—H2102.8O11—P1—C31111.63 (11)
C3—C2—H2102.8C21—P1—C31106.49 (12)
C2—C3—C4110.7 (9)C11—P1—C31106.48 (11)
C2—C3—H3A109.5C16—C11—C12119.7 (2)
C4—C3—H3A109.5C16—C11—P1123.44 (19)
C2—C3—H3B109.5C12—C11—P1116.83 (19)
C4—C3—H3B109.5C13—C12—C11119.8 (2)
H3A—C3—H3B108.1C13—C12—H12120.1
C5—C4—C3112.9 (11)C11—C12—H12120.1
C5—C4—H4A109.0C14—C13—C12120.5 (3)
C3—C4—H4A109.0C14—C13—H13119.8
C5—C4—H4B109.0C12—C13—H13119.8
C3—C4—H4B109.0C13—C14—C15119.9 (3)
H4A—C4—H4B107.8C13—C14—H14120.0
C4—C5—C6110.3 (9)C15—C14—H14120.0
C4—C5—H5A109.6C16—C15—C14120.4 (3)
C6—C5—H5A109.6C16—C15—H15119.8
C4—C5—H5B109.6C14—C15—H15119.8
C6—C5—H5B109.6C11—C16—C15119.6 (2)
H5A—C5—H5B108.1C11—C16—H16120.2
C1—C6—C5111.5 (10)C15—C16—H16120.2
C1—C6—H6A109.3C26—C21—C22119.0 (2)
C5—C6—H6A109.3C26—C21—P1123.0 (2)
C1—C6—H6B109.3C22—C21—P1117.94 (19)
C5—C6—H6B109.3C23—C22—C21120.0 (3)
H6A—C6—H6B108.0C23—C22—H22120.0
O1'—C1'—C2'111.1 (7)C21—C22—H22120.0
O1'—C1'—C6'107.9 (8)C24—C23—C22120.4 (3)
C2'—C1'—C6'110.3 (9)C24—C23—H23119.8
O1'—C1'—H1'109.2C22—C23—H23119.8
C2'—C1'—H1'109.2C25—C24—C23119.8 (3)
C6'—C1'—H1'109.2C25—C24—H24120.1
O2'—C2'—C1'119.8 (9)C23—C24—H24120.1
O2'—C2'—C3'113.4 (11)C24—C25—C26120.2 (3)
C1'—C2'—C3'110.4 (8)C24—C25—H25119.9
O2'—C2'—H2'103.7C26—C25—H25119.9
C1'—C2'—H2'103.7C21—C26—C25120.5 (3)
C3'—C2'—H2'103.7C21—C26—H26119.8
C2'—C3'—C4'110.5 (9)C25—C26—H26119.8
C2'—C3'—H3'A109.6C32—C31—C36119.0 (2)
C4'—C3'—H3'A109.6C32—C31—P1118.04 (19)
C2'—C3'—H3'B109.6C36—C31—P1123.00 (19)
C4'—C3'—H3'B109.6C31—C32—C33120.7 (2)
H3'A—C3'—H3'B108.1C31—C32—H32119.6
C5'—C4'—C3'109.8 (11)C33—C32—H32119.6
C5'—C4'—H4'A109.7C34—C33—C32119.8 (3)
C3'—C4'—H4'A109.7C34—C33—H33120.1
C5'—C4'—H4'B109.7C32—C33—H33120.1
C3'—C4'—H4'B109.7C33—C34—C35119.9 (2)
H4'A—C4'—H4'B108.2C33—C34—H34120.0
C6'—C5'—C4'110.7 (9)C35—C34—H34120.0
C6'—C5'—H5'A109.5C36—C35—C34120.0 (2)
C4'—C5'—H5'A109.5C36—C35—H35120.0
C6'—C5'—H5'B109.5C34—C35—H35120.0
C4'—C5'—H5'B109.5C35—C36—C31120.6 (2)
H5'A—C5'—H5'B108.1C35—C36—H36119.7
C1'—C6'—C5'111.5 (10)C31—C36—H36119.7
O1—C1—C2—O239.2 (12)C13—C14—C15—C160.2 (4)
C6—C1—C2—O2163.4 (10)C12—C11—C16—C152.4 (4)
O1—C1—C2—C3179.9 (7)P1—C11—C16—C15177.17 (19)
C6—C1—C2—C355.6 (13)C14—C15—C16—C111.8 (4)
O2—C2—C3—C4169.5 (14)O11—P1—C21—C26114.2 (2)
C1—C2—C3—C454.1 (14)C11—P1—C21—C26122.3 (2)
C2—C3—C4—C554.4 (18)C31—P1—C21—C269.2 (2)
C3—C4—C5—C654.5 (19)O11—P1—C21—C2263.0 (2)
O1—C1—C6—C5177.7 (9)C11—P1—C21—C2260.5 (2)
C2—C1—C6—C556.0 (15)C31—P1—C21—C22173.6 (2)
C4—C5—C6—C154.6 (17)C26—C21—C22—C231.2 (4)
O1'—C1'—C2'—O2'47.8 (14)P1—C21—C22—C23176.1 (2)
C6'—C1'—C2'—O2'167.4 (13)C21—C22—C23—C240.2 (4)
O1'—C1'—C2'—C3'177.8 (6)C22—C23—C24—C250.8 (4)
C6'—C1'—C2'—C3'58.1 (12)C23—C24—C25—C260.8 (4)
O2'—C2'—C3'—C4'163.2 (11)C22—C21—C26—C251.2 (4)
C1'—C2'—C3'—C4'59.2 (13)P1—C21—C26—C25176.0 (2)
C2'—C3'—C4'—C5'57.9 (17)C24—C25—C26—C210.2 (4)
C3'—C4'—C5'—C6'56.0 (17)O11—P1—C31—C3221.0 (2)
O1'—C1'—C6'—C5'178.2 (9)C21—P1—C31—C32103.8 (2)
C2'—C1'—C6'—C5'56.7 (15)C11—P1—C31—C32143.5 (2)
C4'—C5'—C6'—C1'55.9 (16)O11—P1—C31—C36158.72 (19)
O11—P1—C11—C16158.2 (2)C21—P1—C31—C3676.5 (2)
C21—P1—C11—C1633.5 (2)C11—P1—C31—C3636.2 (2)
C31—P1—C11—C1679.6 (2)C36—C31—C32—C331.4 (4)
O11—P1—C11—C1222.2 (2)P1—C31—C32—C33178.28 (19)
C21—P1—C11—C12146.89 (19)C31—C32—C33—C340.8 (4)
C31—P1—C11—C12100.0 (2)C32—C33—C34—C350.5 (4)
C16—C11—C12—C131.5 (4)C33—C34—C35—C361.3 (4)
P1—C11—C12—C13178.08 (19)C34—C35—C36—C310.7 (4)
C11—C12—C13—C140.0 (4)C32—C31—C36—C350.6 (4)
C12—C13—C14—C150.6 (4)P1—C31—C36—C35179.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H01···O1i0.841.852.63 (2)156
O2—H02···O1ii0.842.323.082 (14)151
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+1, z.
(toluene90KmonoCuKa) 1:1 rac-1,2-cyclohexanediol triphenylphosphine oxide top
Crystal data top
C6H12O2·C18H15OPF(000) = 1680
Mr = 394.43Dx = 1.267 Mg m3
Monoclinic, C12/c1Cu Kα radiation, λ = 1.54178 Å
a = 41.597 (4) ÅCell parameters from 7792 reflections
b = 9.271 (1) Åθ = 2.2–67.8°
c = 10.923 (1) ŵ = 1.35 mm1
β = 101.04 (1)°T = 90 K
V = 4134.5 (7) Å3Lath, colorless
Z = 80.20 × 0.12 × 0.04 mm
Data collection top
Bruker-Nonius X8 Proteum
diffractometer
3742 independent reflections
Radiation source: fine-focus rotating anode3401 reflections with I > 2σ(I)
Graded multi-layer optics monochromatorRint = 0.059
Detector resolution: 18 pixels mm-1θmax = 68.1°, θmin = 2.2°
ω and ϕ scansh = 4949
Absorption correction: multi-scan
SADABS in APEX2 (Bruker-Nonius, 2004)
k = 1011
Tmin = 0.774, Tmax = 0.948l = 1313
27070 measured 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116H-atom parameters constrained
S = 1.18 w = 1/[σ2(Fo2) + (0.P)2 + 10.8979P]
where P = (Fo2 + 2Fc2)/3
3742 reflections(Δ/σ)max = 0.001
282 parametersΔρmax = 0.26 e Å3
68 restraintsΔρmin = 0.33 e Å3
Crystal data top
C6H12O2·C18H15OPV = 4134.5 (7) Å3
Mr = 394.43Z = 8
Monoclinic, C12/c1Cu Kα radiation
a = 41.597 (4) ŵ = 1.35 mm1
b = 9.271 (1) ÅT = 90 K
c = 10.923 (1) Å0.20 × 0.12 × 0.04 mm
β = 101.04 (1)°
Data collection top
Bruker-Nonius X8 Proteum
diffractometer
3742 independent reflections
Absorption correction: multi-scan
SADABS in APEX2 (Bruker-Nonius, 2004)
3401 reflections with I > 2σ(I)
Tmin = 0.774, Tmax = 0.948Rint = 0.059
27070 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.04968 restraints
wR(F2) = 0.116H-atom parameters constrained
S = 1.18 w = 1/[σ2(Fo2) + (0.P)2 + 10.8979P]
where P = (Fo2 + 2Fc2)/3
3742 reflectionsΔρmax = 0.26 e Å3
282 parametersΔρmin = 0.33 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.0185 (2)0.7573 (9)0.0767 (8)0.0241 (13)0.475 (4)
H10.00000.82750.05670.029*0.475 (4)
C20.0291 (2)0.7168 (9)0.0441 (9)0.0254 (15)0.475 (4)
H20.04900.65660.01520.031*0.475 (4)
C30.0425 (2)0.8469 (8)0.1027 (9)0.0329 (15)0.475 (4)
H3A0.02470.91790.12850.039*0.475 (4)
H3B0.05060.81610.17810.039*0.475 (4)
C40.0702 (5)0.917 (2)0.0113 (11)0.037 (2)0.475 (4)
H4A0.08910.85020.00630.045*0.475 (4)
H4B0.07741.00530.04970.045*0.475 (4)
C50.05995 (17)0.9570 (7)0.1099 (7)0.0336 (10)0.475 (4)
H5A0.07910.99440.16930.040*0.475 (4)
H5B0.04331.03460.09420.040*0.475 (4)
C60.0460 (4)0.8286 (18)0.1670 (12)0.032 (2)0.475 (4)
H6A0.06360.75740.19440.038*0.475 (4)
H6B0.03760.86050.24160.038*0.475 (4)
O10.00672 (16)0.6316 (8)0.1263 (8)0.0305 (11)0.475 (4)
H010.00930.59890.07530.046*0.475 (4)
O20.0076 (5)0.6212 (14)0.1129 (16)0.0358 (19)0.475 (4)
H020.00680.63650.18920.054*0.475 (4)
C1'0.02685 (18)0.7185 (8)0.0878 (7)0.0241 (13)0.525 (4)
H1'0.04320.63830.10450.029*0.525 (4)
C2'0.02041 (18)0.7526 (9)0.0499 (7)0.0254 (15)0.525 (4)
H2'0.00620.84050.05770.031*0.525 (4)
C3'0.05165 (17)0.8038 (8)0.0888 (8)0.0329 (15)0.525 (4)
H3'A0.04710.82730.17890.039*0.525 (4)
H3'B0.06820.72570.07480.039*0.525 (4)
C4'0.0652 (4)0.9370 (19)0.0140 (10)0.037 (2)0.525 (4)
H4'A0.08590.96680.03820.045*0.525 (4)
H4'B0.04931.01740.03340.045*0.525 (4)
C5'0.07124 (14)0.9059 (7)0.1254 (6)0.0336 (10)0.525 (4)
H5'A0.08910.83420.14640.040*0.525 (4)
H5'B0.07830.99560.17210.040*0.525 (4)
C6'0.0405 (4)0.8483 (16)0.1642 (11)0.032 (2)0.525 (4)
H6'A0.04560.82130.25350.038*0.525 (4)
H6'B0.02360.92530.15400.038*0.525 (4)
O1'0.00322 (15)0.6729 (7)0.1266 (7)0.0305 (11)0.525 (4)
H01'0.00120.64230.20030.046*0.525 (4)
O2'0.0029 (4)0.6560 (13)0.1322 (13)0.0358 (19)0.525 (4)
H02'0.00410.57380.09940.054*0.525 (4)
P10.167801 (13)0.61855 (6)0.16176 (5)0.01735 (15)
O110.17058 (4)0.67210 (16)0.29154 (14)0.0226 (4)
C110.13367 (5)0.4960 (2)0.1190 (2)0.0188 (4)
C120.10830 (5)0.5060 (2)0.1858 (2)0.0227 (5)
H120.10980.57310.25230.027*
C130.08097 (6)0.4188 (3)0.1557 (2)0.0298 (6)
H130.06390.42550.20200.036*
C140.07849 (6)0.3218 (3)0.0580 (3)0.0320 (6)
H140.05950.26320.03630.038*
C150.10375 (6)0.3100 (3)0.0083 (2)0.0277 (5)
H150.10210.24270.07480.033*
C160.13148 (5)0.3965 (2)0.0223 (2)0.0219 (5)
H160.14880.38760.02250.026*
C210.20337 (5)0.5219 (2)0.1346 (2)0.0199 (5)
C220.21195 (6)0.3948 (3)0.2014 (2)0.0299 (5)
H220.19840.35890.25530.036*
C230.24008 (6)0.3208 (3)0.1893 (3)0.0359 (6)
H230.24560.23380.23430.043*
C240.26018 (6)0.3730 (3)0.1119 (2)0.0313 (6)
H240.27970.32310.10520.038*
C250.25171 (6)0.4975 (3)0.0447 (2)0.0315 (6)
H250.26530.53290.00910.038*
C260.22330 (6)0.5716 (3)0.0554 (2)0.0261 (5)
H260.21750.65690.00810.031*
C310.16116 (5)0.7645 (2)0.0495 (2)0.0200 (5)
C320.17042 (5)0.9033 (2)0.0926 (2)0.0214 (5)
H320.18020.91820.17760.026*
C330.16521 (6)1.0194 (2)0.0107 (2)0.0266 (5)
H330.17141.11370.04020.032*
C340.15116 (6)0.9989 (3)0.1130 (2)0.0277 (5)
H340.14741.07900.16810.033*
C350.14256 (6)0.8604 (3)0.1570 (2)0.0288 (5)
H350.13340.84560.24260.035*
C360.14746 (6)0.7441 (3)0.0757 (2)0.0249 (5)
H360.14140.64990.10580.030*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.020 (3)0.023 (4)0.0284 (17)0.000 (2)0.001 (2)0.002 (2)
C20.029 (4)0.020 (4)0.0277 (14)0.002 (3)0.006 (2)0.004 (2)
C30.037 (4)0.030 (4)0.036 (2)0.006 (3)0.015 (3)0.004 (3)
C40.035 (5)0.030 (4)0.0500 (16)0.012 (4)0.0163 (18)0.0045 (18)
C50.024 (3)0.027 (3)0.047 (2)0.0035 (18)0.000 (2)0.006 (2)
C60.036 (4)0.030 (4)0.0274 (14)0.005 (4)0.001 (2)0.0049 (18)
O10.030 (3)0.032 (3)0.0302 (10)0.0078 (18)0.008 (2)0.001 (2)
O20.049 (5)0.030 (5)0.027 (4)0.014 (4)0.004 (3)0.002 (3)
C1'0.020 (3)0.023 (4)0.0284 (17)0.000 (2)0.001 (2)0.002 (2)
C2'0.029 (4)0.020 (4)0.0277 (14)0.002 (3)0.006 (2)0.004 (2)
C3'0.037 (4)0.030 (4)0.036 (2)0.006 (3)0.015 (3)0.004 (3)
C4'0.035 (5)0.030 (4)0.0500 (16)0.012 (4)0.0163 (18)0.0045 (18)
C5'0.024 (3)0.027 (3)0.047 (2)0.0035 (18)0.000 (2)0.006 (2)
C6'0.036 (4)0.030 (4)0.0274 (14)0.005 (4)0.001 (2)0.0049 (18)
O1'0.030 (3)0.032 (3)0.0302 (10)0.0078 (18)0.008 (2)0.001 (2)
O2'0.049 (5)0.030 (5)0.027 (4)0.014 (4)0.004 (3)0.002 (3)
P10.0175 (3)0.0158 (3)0.0187 (3)0.0003 (2)0.0033 (2)0.0002 (2)
O110.0263 (8)0.0198 (8)0.0218 (8)0.0016 (6)0.0054 (6)0.0013 (6)
C110.0201 (10)0.0158 (10)0.0197 (10)0.0020 (8)0.0018 (8)0.0043 (8)
C120.0204 (11)0.0222 (12)0.0257 (12)0.0042 (9)0.0047 (9)0.0032 (9)
C130.0187 (11)0.0306 (13)0.0408 (14)0.0009 (10)0.0075 (10)0.0063 (11)
C140.0192 (11)0.0246 (13)0.0487 (16)0.0051 (10)0.0021 (11)0.0052 (11)
C150.0290 (12)0.0197 (12)0.0312 (13)0.0011 (10)0.0023 (10)0.0013 (10)
C160.0248 (11)0.0166 (11)0.0237 (11)0.0020 (9)0.0029 (9)0.0030 (9)
C210.0160 (10)0.0219 (11)0.0206 (11)0.0014 (9)0.0006 (8)0.0033 (9)
C220.0282 (12)0.0327 (14)0.0294 (13)0.0070 (11)0.0070 (10)0.0088 (11)
C230.0305 (13)0.0374 (15)0.0367 (14)0.0133 (11)0.0010 (11)0.0075 (12)
C240.0199 (11)0.0364 (14)0.0351 (13)0.0078 (10)0.0007 (10)0.0085 (11)
C250.0241 (12)0.0333 (14)0.0393 (14)0.0015 (10)0.0117 (11)0.0030 (11)
C260.0256 (12)0.0229 (12)0.0306 (12)0.0006 (9)0.0068 (10)0.0013 (10)
C310.0171 (10)0.0197 (11)0.0243 (11)0.0015 (8)0.0072 (8)0.0005 (9)
C320.0204 (11)0.0182 (11)0.0266 (12)0.0001 (9)0.0070 (9)0.0005 (9)
C330.0258 (12)0.0160 (11)0.0405 (14)0.0010 (9)0.0127 (10)0.0004 (10)
C340.0279 (12)0.0215 (12)0.0366 (13)0.0056 (10)0.0134 (10)0.0101 (10)
C350.0315 (13)0.0305 (13)0.0243 (12)0.0022 (10)0.0050 (10)0.0050 (10)
C360.0274 (12)0.0200 (12)0.0268 (12)0.0022 (9)0.0041 (9)0.0007 (10)
Geometric parameters (Å, º) top
C1—O11.412 (13)O2'—H02'0.8400
C1—C61.511 (12)P1—O111.4855 (16)
C1—C21.514 (10)P1—C211.802 (2)
C1—H11.0000P1—C111.808 (2)
C2—O21.37 (2)P1—C311.812 (2)
C2—C31.521 (10)C11—C161.393 (3)
C2—H21.0000C11—C121.396 (3)
C3—C41.521 (12)C12—C131.382 (3)
C3—H3A0.9900C12—H120.9500
C3—H3B0.9900C13—C141.384 (4)
C4—C51.512 (12)C13—H130.9500
C4—H4A0.9900C14—C151.390 (4)
C4—H4B0.9900C14—H140.9500
C5—C61.512 (12)C15—C161.391 (3)
C5—H5A0.9900C15—H150.9500
C5—H5B0.9900C16—H160.9500
C6—H6A0.9900C21—C261.386 (3)
C6—H6B0.9900C21—C221.396 (3)
O1—H010.8400C22—C231.384 (4)
O2—H020.8400C22—H220.9500
C1'—O1'1.458 (11)C23—C241.385 (4)
C1'—C2'1.510 (9)C23—H230.9500
C1'—C6'1.512 (11)C24—C251.377 (4)
C1'—H1'1.0000C24—H240.9500
C2'—O2'1.374 (17)C25—C261.391 (3)
C2'—C3'1.519 (9)C25—H250.9500
C2'—H2'1.0000C26—H260.9500
C3'—C4'1.527 (11)C31—C361.391 (3)
C3'—H3'A0.9900C31—C321.399 (3)
C3'—H3'B0.9900C32—C331.390 (3)
C4'—C5'1.522 (12)C32—H320.9500
C4'—H4'A0.9900C33—C341.379 (4)
C4'—H4'B0.9900C33—H330.9500
C5'—C6'1.521 (11)C34—C351.393 (4)
C5'—H5'A0.9900C34—H340.9500
C5'—H5'B0.9900C35—C361.386 (3)
C6'—H6'A0.9900C35—H350.9500
C6'—H6'B0.9900C36—H360.9500
O1'—H01'0.8400
O1—C1—C6112.6 (8)C1'—C6'—H6'A109.3
O1—C1—C2108.1 (7)C5'—C6'—H6'A109.3
C6—C1—C2111.7 (9)C1'—C6'—H6'B109.3
O1—C1—H1108.1C5'—C6'—H6'B109.3
C6—C1—H1108.1H6'A—C6'—H6'B107.9
C2—C1—H1108.1C1'—O1'—H01'109.5
O2—C2—C1111.7 (11)C2'—O2'—H02'109.5
O2—C2—C3122.2 (9)O11—P1—C21114.02 (9)
C1—C2—C3111.2 (7)O11—P1—C11111.72 (9)
O2—C2—H2103.0C21—P1—C11105.89 (10)
C1—C2—H2103.0O11—P1—C31111.73 (10)
C3—C2—H2103.0C21—P1—C31106.45 (10)
C2—C3—C4111.0 (9)C11—P1—C31106.52 (10)
C2—C3—H3A109.4C16—C11—C12119.6 (2)
C4—C3—H3A109.4C16—C11—P1123.12 (17)
C2—C3—H3B109.4C12—C11—P1117.29 (17)
C4—C3—H3B109.4C13—C12—C11120.4 (2)
H3A—C3—H3B108.0C13—C12—H12119.8
C5—C4—C3111.9 (11)C11—C12—H12119.8
C5—C4—H4A109.2C12—C13—C14120.0 (2)
C3—C4—H4A109.2C12—C13—H13120.0
C5—C4—H4B109.2C14—C13—H13120.0
C3—C4—H4B109.2C13—C14—C15120.0 (2)
H4A—C4—H4B107.9C13—C14—H14120.0
C6—C5—C4111.4 (9)C15—C14—H14120.0
C6—C5—H5A109.3C14—C15—C16120.3 (2)
C4—C5—H5A109.3C14—C15—H15119.9
C6—C5—H5B109.3C16—C15—H15119.9
C4—C5—H5B109.3C15—C16—C11119.7 (2)
H5A—C5—H5B108.0C15—C16—H16120.2
C1—C6—C5112.2 (10)C11—C16—H16120.2
C1—C6—H6A109.2C26—C21—C22118.9 (2)
C5—C6—H6A109.2C26—C21—P1123.07 (18)
C1—C6—H6B109.2C22—C21—P1117.99 (17)
C5—C6—H6B109.2C23—C22—C21120.3 (2)
H6A—C6—H6B107.9C23—C22—H22119.8
O1'—C1'—C2'110.6 (6)C21—C22—H22119.8
O1'—C1'—C6'108.8 (7)C22—C23—C24120.3 (2)
C2'—C1'—C6'111.1 (8)C22—C23—H23119.8
O1'—C1'—H1'108.8C24—C23—H23119.8
C2'—C1'—H1'108.8C25—C24—C23119.7 (2)
C6'—C1'—H1'108.8C25—C24—H24120.2
O2'—C2'—C1'119.1 (8)C23—C24—H24120.2
O2'—C2'—C3'113.2 (10)C24—C25—C26120.3 (2)
C1'—C2'—C3'110.2 (7)C24—C25—H25119.9
O2'—C2'—H2'104.2C26—C25—H25119.9
C1'—C2'—H2'104.2C21—C26—C25120.5 (2)
C3'—C2'—H2'104.2C21—C26—H26119.8
C2'—C3'—C4'110.4 (8)C25—C26—H26119.8
C2'—C3'—H3'A109.6C36—C31—C32119.4 (2)
C4'—C3'—H3'A109.6C36—C31—P1123.01 (17)
C2'—C3'—H3'B109.6C32—C31—P1117.57 (17)
C4'—C3'—H3'B109.6C33—C32—C31119.8 (2)
H3'A—C3'—H3'B108.1C33—C32—H32120.1
C5'—C4'—C3'110.9 (10)C31—C32—H32120.1
C5'—C4'—H4'A109.5C34—C33—C32120.6 (2)
C3'—C4'—H4'A109.5C34—C33—H33119.7
C5'—C4'—H4'B109.5C32—C33—H33119.7
C3'—C4'—H4'B109.5C33—C34—C35119.8 (2)
H4'A—C4'—H4'B108.1C33—C34—H34120.1
C6'—C5'—C4'111.0 (8)C35—C34—H34120.1
C6'—C5'—H5'A109.4C36—C35—C34120.0 (2)
C4'—C5'—H5'A109.4C36—C35—H35120.0
C6'—C5'—H5'B109.4C34—C35—H35120.0
C4'—C5'—H5'B109.4C35—C36—C31120.4 (2)
H5'A—C5'—H5'B108.0C35—C36—H36119.8
C1'—C6'—C5'111.8 (9)C31—C36—H36119.8
O1—C1—C2—O240.3 (10)C13—C14—C15—C160.6 (4)
C6—C1—C2—O2164.7 (11)C14—C15—C16—C110.6 (3)
O1—C1—C2—C3179.4 (6)C12—C11—C16—C151.2 (3)
C6—C1—C2—C354.9 (12)P1—C11—C16—C15177.28 (17)
O2—C2—C3—C4169.3 (14)O11—P1—C21—C26114.33 (19)
C1—C2—C3—C455.2 (13)C11—P1—C21—C26122.43 (19)
C2—C3—C4—C555.0 (18)C31—P1—C21—C269.3 (2)
C3—C4—C5—C654.0 (19)O11—P1—C21—C2262.5 (2)
O1—C1—C6—C5176.1 (10)C11—P1—C21—C2260.8 (2)
C2—C1—C6—C554.3 (16)C31—P1—C21—C22173.89 (18)
C4—C5—C6—C153.6 (18)C26—C21—C22—C230.6 (4)
O1'—C1'—C2'—O2'48.1 (12)P1—C21—C22—C23176.3 (2)
C6'—C1'—C2'—O2'169.0 (12)C21—C22—C23—C240.7 (4)
O1'—C1'—C2'—C3'178.5 (5)C22—C23—C24—C251.4 (4)
C6'—C1'—C2'—C3'57.7 (11)C23—C24—C25—C260.7 (4)
O2'—C2'—C3'—C4'165.5 (10)C22—C21—C26—C251.3 (3)
C1'—C2'—C3'—C4'58.3 (11)P1—C21—C26—C25175.49 (18)
C2'—C3'—C4'—C5'57.1 (15)C24—C25—C26—C210.6 (4)
C3'—C4'—C5'—C6'54.7 (16)O11—P1—C31—C36158.54 (18)
O1'—C1'—C6'—C5'177.7 (9)C21—P1—C31—C3676.4 (2)
C2'—C1'—C6'—C5'55.8 (14)C11—P1—C31—C3636.3 (2)
C4'—C5'—C6'—C1'54.1 (16)O11—P1—C31—C3221.5 (2)
O11—P1—C11—C16158.73 (17)C21—P1—C31—C32103.61 (18)
C21—P1—C11—C1634.0 (2)C11—P1—C31—C32143.72 (17)
C31—P1—C11—C1679.0 (2)C36—C31—C32—C331.3 (3)
O11—P1—C11—C1222.7 (2)P1—C31—C32—C33178.67 (17)
C21—P1—C11—C12147.40 (17)C31—C32—C33—C340.4 (3)
C31—P1—C11—C1299.55 (18)C32—C33—C34—C351.0 (3)
C16—C11—C12—C130.6 (3)C33—C34—C35—C361.5 (4)
P1—C11—C12—C13177.99 (18)C34—C35—C36—C310.5 (4)
C11—C12—C13—C140.6 (4)C32—C31—C36—C350.9 (3)
C12—C13—C14—C151.2 (4)P1—C31—C36—C35179.12 (18)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H01···O1i0.841.902.658 (15)150
O2—H02···O1ii0.842.313.050 (14)148
Symmetry codes: (i) x, y, z+1/2; (ii) x, y+1, z.
(acetone294Ktri) 1:1 rac-1,2-cyclohexanediol triphenylphosphine oxide top
Crystal data top
C6H12O2·C18H15OPZ = 4
Mr = 394.43F(000) = 840
Triclinic, P1Dx = 1.232 Mg m3
a = 9.348 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.000 (2) ÅCell parameters from 9671 reflections
c = 21.550 (3) Åθ = 1.0–27.5°
α = 100.18 (1)°µ = 0.15 mm1
β = 102.44 (1)°T = 294 K
γ = 90.50 (1)°Lath, colorless
V = 2127.3 (7) Å30.30 × 0.20 × 0.07 mm
Data collection top
Nonius KappaCCD
diffractometer
7480 independent reflections
Radiation source: fine-focus sealed tube4582 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
Detector resolution: 10 pixels mm-1θmax = 25.0°, θmin = 1.9°
1.0° ω scans at fixed χ = 55°h = 1111
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
k = 1313
Tmin = 0.96, Tmax = 0.99l = 2525
14927 measured 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: inferred from neighbouring sites
wR(F2) = 0.117H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0522P)2 + 0.1732P]
where P = (Fo2 + 2Fc2)/3
7480 reflections(Δ/σ)max = 0.001
564 parametersΔρmax = 0.17 e Å3
148 restraintsΔρmin = 0.26 e Å3
Crystal data top
C6H12O2·C18H15OPγ = 90.50 (1)°
Mr = 394.43V = 2127.3 (7) Å3
Triclinic, P1Z = 4
a = 9.348 (2) ÅMo Kα radiation
b = 11.000 (2) ŵ = 0.15 mm1
c = 21.550 (3) ÅT = 294 K
α = 100.18 (1)°0.30 × 0.20 × 0.07 mm
β = 102.44 (1)°
Data collection top
Nonius KappaCCD
diffractometer
7480 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
4582 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.99Rint = 0.040
14927 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.047148 restraints
wR(F2) = 0.117H-atom parameters constrained
S = 1.02Δρmax = 0.17 e Å3
7480 reflectionsΔρmin = 0.26 e Å3
564 parameters
Special details top

Experimental. The crystal-to-detector distance was 43 mm. Each frame was measured for 50 s. The number of scan sets measured was 9; the total number of frames measured was 987.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.7760 (3)0.0752 (3)0.03733 (16)0.0474 (8)0.861 (5)
H1A0.82660.05660.00160.057*0.861 (5)
C2A0.7446 (3)0.0437 (3)0.05823 (17)0.0506 (9)0.861 (5)
H2A0.68860.02720.09220.061*0.861 (5)
C3A0.8867 (4)0.1015 (3)0.0837 (2)0.0685 (12)0.861 (5)
H3A10.93790.12430.04900.082*0.861 (5)
H3A20.86520.17610.09880.082*0.861 (5)
C4A0.9846 (4)0.0122 (4)0.1388 (2)0.0828 (14)0.861 (5)
H4A10.93730.00420.17510.099*0.861 (5)
H4A21.07660.04980.15280.099*0.861 (5)
C5A1.0149 (4)0.1086 (3)0.11818 (19)0.0733 (11)0.861 (5)
H5A11.07120.16600.15490.088*0.861 (5)
H5A21.07230.09390.08530.088*0.861 (5)
C6A0.8725 (5)0.1640 (3)0.0918 (3)0.0644 (9)0.861 (5)
H6A10.82060.18710.12620.077*0.861 (5)
H6A20.89350.23840.07630.077*0.861 (5)
O1A0.6377 (3)0.1256 (3)0.01408 (17)0.0643 (11)0.861 (5)
H1A10.65190.19400.00570.097*0.861 (5)
O2A0.6615 (3)0.1308 (3)0.00392 (15)0.0654 (9)0.861 (5)
H2A10.57550.11230.00340.098*0.861 (5)
C1A'0.7438 (17)0.0758 (13)0.0586 (8)0.0474 (8)0.139 (5)
H1A'0.68190.08410.09030.057*0.139 (5)
C2A'0.7746 (17)0.0584 (13)0.0417 (8)0.0506 (9)0.139 (5)
H2A'0.82270.07160.00510.061*0.139 (5)
C3A'0.870 (2)0.1022 (16)0.0992 (13)0.0685 (12)0.139 (5)
H3A30.89340.18730.08650.082*0.139 (5)
H3A40.81600.09880.13330.082*0.139 (5)
C4A'1.0108 (19)0.0215 (19)0.1245 (14)0.0828 (14)0.139 (5)
H4A31.07010.05020.16140.099*0.139 (5)
H4A41.06670.02750.09110.099*0.139 (5)
C5A'0.974 (2)0.1120 (19)0.1443 (10)0.0733 (11)0.139 (5)
H5A30.92230.11850.17900.088*0.139 (5)
H5A41.06430.16330.15990.088*0.139 (5)
C6A'0.881 (3)0.1566 (16)0.0874 (16)0.0644 (9)0.139 (5)
H6A30.85430.24050.10110.077*0.139 (5)
H6A40.93740.15780.05460.077*0.139 (5)
O1A'0.662 (3)0.112 (2)0.0009 (11)0.0643 (11)0.139 (5)
H1A20.58220.07440.01050.097*0.139 (5)
O2A'0.638 (2)0.1319 (18)0.0255 (10)0.0654 (9)0.139 (5)
H2A20.65470.20550.01870.098*0.139 (5)
C1B0.3097 (4)0.5867 (2)0.05295 (16)0.0498 (8)0.915 (6)
H1B0.40320.60100.08480.060*0.915 (6)
C2B0.2671 (4)0.4508 (2)0.03890 (15)0.0487 (8)0.915 (6)
H2B0.17570.43610.00580.058*0.915 (6)
C3B0.2423 (5)0.4086 (3)0.0988 (2)0.0738 (12)0.915 (6)
H3B10.33350.41850.13120.089*0.915 (6)
H3B20.21140.32160.08850.089*0.915 (6)
C4B0.1256 (5)0.4835 (4)0.1259 (2)0.0856 (13)0.915 (6)
H4B10.03220.46750.09510.103*0.915 (6)
H4B20.11480.45800.16560.103*0.915 (6)
C5B0.1671 (5)0.6201 (3)0.13938 (17)0.0790 (11)0.915 (6)
H5B10.08840.66620.15360.095*0.915 (6)
H5B20.25430.63740.17390.095*0.915 (6)
C6B0.1959 (5)0.6617 (3)0.0799 (2)0.0659 (10)0.915 (6)
H6B10.10530.65380.04720.079*0.915 (6)
H6B20.22900.74820.09080.079*0.915 (6)
O1B0.3269 (3)0.6283 (2)0.00472 (14)0.0636 (8)0.915 (6)
H1B10.40340.60350.01410.095*0.915 (6)
O2B0.3800 (7)0.3856 (3)0.0140 (3)0.0675 (8)0.915 (6)
H2B10.36070.31090.00790.101*0.915 (6)
C1B'0.269 (3)0.579 (2)0.0396 (12)0.0498 (8)0.085 (6)
H1B'0.18580.55670.00250.060*0.085 (6)
C2B'0.323 (3)0.462 (2)0.0623 (16)0.0487 (8)0.085 (6)
H2B'0.40920.48360.09770.058*0.085 (6)
C3B'0.207 (4)0.400 (2)0.087 (2)0.0738 (12)0.085 (6)
H3B30.24670.32880.10420.089*0.085 (6)
H3B40.12400.37140.05140.089*0.085 (6)
C4B'0.155 (5)0.489 (4)0.1395 (19)0.0856 (13)0.085 (6)
H4B30.07660.44900.15260.103*0.085 (6)
H4B40.23540.51100.17700.103*0.085 (6)
C5B'0.101 (4)0.605 (3)0.1155 (19)0.0790 (11)0.085 (6)
H5B30.01490.58420.08060.095*0.085 (6)
H5B40.07340.66200.15020.095*0.085 (6)
C6B'0.219 (5)0.666 (2)0.092 (2)0.0659 (10)0.085 (6)
H6B30.18060.73860.07490.079*0.085 (6)
H6B40.30140.69330.12750.079*0.085 (6)
O1B'0.382 (3)0.641 (3)0.0197 (15)0.0636 (8)0.085 (6)
H1B20.34830.70090.00440.095*0.085 (6)
O2B'0.365 (8)0.383 (3)0.010 (3)0.0675 (8)0.085 (6)
H2B20.44370.40860.00540.101*0.085 (6)
P01A0.78813 (7)0.16297 (6)0.33633 (3)0.04564 (19)
O11A0.84548 (17)0.29115 (14)0.34108 (8)0.0578 (5)
C11A0.6345 (2)0.1196 (2)0.26892 (11)0.0434 (6)
C12A0.6218 (3)0.1837 (2)0.21800 (12)0.0536 (7)
H12A0.68920.24800.22050.064*
C13A0.5097 (3)0.1523 (3)0.16379 (13)0.0668 (8)
H13A0.50170.19560.12990.080*
C14A0.4105 (3)0.0579 (3)0.15983 (14)0.0706 (8)
H14A0.33590.03640.12300.085*
C15A0.4205 (3)0.0053 (3)0.20986 (14)0.0653 (8)
H15A0.35220.06920.20690.078*
C16A0.5316 (2)0.0254 (2)0.26484 (12)0.0523 (6)
H16A0.53720.01720.29890.063*
C21A0.7250 (3)0.1383 (2)0.40628 (11)0.0483 (6)
C22A0.6096 (3)0.2036 (3)0.42261 (14)0.0816 (9)
H22A0.56230.25580.39600.098*
C23A0.5632 (4)0.1923 (3)0.47838 (18)0.0975 (11)
H23A0.48440.23640.48860.117*
C24A0.6312 (4)0.1181 (3)0.51806 (15)0.0866 (10)
H24A0.60140.11300.55600.104*
C25A0.7425 (4)0.0516 (3)0.50219 (15)0.0915 (10)
H25A0.78780.00150.52870.110*
C26A0.7901 (3)0.0619 (3)0.44646 (13)0.0717 (8)
H26A0.86760.01590.43630.086*
C31A0.9253 (2)0.0521 (2)0.32494 (11)0.0444 (6)
C32A1.0708 (3)0.0935 (2)0.34213 (12)0.0567 (7)
H32A1.09530.17610.36060.068*
C33A1.1806 (3)0.0138 (3)0.33226 (13)0.0691 (8)
H33A1.27810.04300.34380.083*
C34A1.1460 (3)0.1075 (3)0.30569 (14)0.0707 (8)
H34A1.22000.16080.29870.085*
C35A1.0027 (3)0.1511 (3)0.28924 (14)0.0713 (8)
H35A0.97940.23430.27190.086*
C36A0.8929 (3)0.0715 (2)0.29846 (12)0.0605 (7)
H36A0.79560.10140.28670.073*
P01B0.54900 (7)0.66127 (6)0.33401 (3)0.04511 (19)
O11B0.49818 (18)0.78902 (14)0.33934 (8)0.0576 (5)
C11B0.6382 (2)0.6215 (2)0.26742 (11)0.0421 (6)
C12B0.6047 (3)0.6885 (2)0.21767 (11)0.0526 (6)
H12B0.54080.75260.22030.063*
C13B0.6660 (3)0.6602 (3)0.16425 (13)0.0686 (8)
H13B0.64360.70570.13120.082*
C14B0.7592 (3)0.5658 (3)0.15989 (14)0.0748 (9)
H14B0.79870.54620.12350.090*
C15B0.7949 (3)0.4997 (3)0.20901 (14)0.0668 (8)
H15B0.85960.43630.20590.080*
C16B0.7353 (2)0.5269 (2)0.26323 (12)0.0526 (6)
H16B0.76010.48210.29650.063*
C21B0.6790 (3)0.6356 (2)0.40451 (11)0.0491 (6)
C22B0.8113 (3)0.7027 (3)0.42228 (15)0.0866 (10)
H22B0.83350.75640.39650.104*
C23B0.9119 (4)0.6909 (3)0.47850 (17)0.1022 (12)
H23B1.00080.73660.48990.123*
C24B0.8815 (4)0.6138 (3)0.51655 (15)0.0839 (10)
H24B0.94820.60740.55450.101*
C25B0.7530 (4)0.5458 (3)0.49917 (15)0.0909 (10)
H25B0.73250.49140.52500.109*
C26B0.6517 (3)0.5564 (3)0.44327 (13)0.0727 (8)
H26B0.56400.50890.43200.087*
C31B0.3988 (2)0.5493 (2)0.32084 (11)0.0456 (6)
C32B0.2721 (3)0.5880 (3)0.34012 (12)0.0583 (7)
H32B0.26770.66950.36030.070*
C33B0.1518 (3)0.5066 (3)0.32969 (14)0.0721 (8)
H33B0.06670.53380.34230.087*
C34B0.1584 (3)0.3867 (3)0.30100 (15)0.0749 (9)
H34B0.07740.33230.29390.090*
C35B0.2828 (3)0.3461 (3)0.28259 (14)0.0764 (9)
H35B0.28720.26390.26350.092*
C36B0.4025 (3)0.4271 (2)0.29227 (13)0.0632 (7)
H36B0.48690.39890.27930.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0394 (16)0.0458 (14)0.060 (2)0.0053 (12)0.0150 (13)0.0118 (14)
C2A0.0448 (17)0.0434 (15)0.065 (2)0.0051 (12)0.0116 (14)0.0139 (14)
C3A0.0523 (18)0.0675 (18)0.093 (3)0.0095 (13)0.0108 (17)0.0403 (18)
C4A0.062 (2)0.109 (2)0.078 (3)0.0077 (18)0.0025 (19)0.039 (2)
C5A0.053 (2)0.089 (2)0.070 (3)0.0096 (17)0.0002 (16)0.0116 (19)
C6A0.0555 (17)0.0550 (17)0.076 (2)0.0048 (13)0.0086 (14)0.0008 (14)
O1A0.0477 (16)0.0442 (14)0.099 (2)0.0072 (10)0.0042 (14)0.0227 (15)
O2A0.0524 (14)0.0427 (11)0.095 (2)0.0006 (10)0.0071 (14)0.0083 (14)
C1A'0.0394 (16)0.0458 (14)0.060 (2)0.0053 (12)0.0150 (13)0.0118 (14)
C2A'0.0448 (17)0.0434 (15)0.065 (2)0.0051 (12)0.0116 (14)0.0139 (14)
C3A'0.0523 (18)0.0675 (18)0.093 (3)0.0095 (13)0.0108 (17)0.0403 (18)
C4A'0.062 (2)0.109 (2)0.078 (3)0.0077 (18)0.0025 (19)0.039 (2)
C5A'0.053 (2)0.089 (2)0.070 (3)0.0096 (17)0.0002 (16)0.0116 (19)
C6A'0.0555 (17)0.0550 (17)0.076 (2)0.0048 (13)0.0086 (14)0.0008 (14)
O1A'0.0477 (16)0.0442 (14)0.099 (2)0.0072 (10)0.0042 (14)0.0227 (15)
O2A'0.0524 (14)0.0427 (11)0.095 (2)0.0006 (10)0.0071 (14)0.0083 (14)
C1B0.047 (2)0.0435 (14)0.0581 (19)0.0025 (13)0.0118 (15)0.0062 (13)
C2B0.0434 (19)0.0458 (14)0.060 (2)0.0057 (13)0.0181 (15)0.0106 (14)
C3B0.078 (3)0.0734 (19)0.092 (3)0.0219 (17)0.044 (2)0.0404 (18)
C4B0.092 (3)0.097 (2)0.092 (3)0.026 (2)0.056 (2)0.036 (2)
C5B0.075 (3)0.092 (2)0.071 (2)0.017 (2)0.030 (2)0.0012 (19)
C6B0.066 (2)0.0510 (16)0.082 (3)0.0099 (14)0.0278 (19)0.0009 (15)
O1B0.0697 (18)0.0479 (12)0.0854 (19)0.0094 (12)0.0343 (14)0.0235 (14)
O2B0.073 (2)0.0426 (10)0.1008 (17)0.0110 (10)0.0473 (16)0.0147 (11)
C1B'0.047 (2)0.0435 (14)0.0581 (19)0.0025 (13)0.0118 (15)0.0062 (13)
C2B'0.0434 (19)0.0458 (14)0.060 (2)0.0057 (13)0.0181 (15)0.0106 (14)
C3B'0.078 (3)0.0734 (19)0.092 (3)0.0219 (17)0.044 (2)0.0404 (18)
C4B'0.092 (3)0.097 (2)0.092 (3)0.026 (2)0.056 (2)0.036 (2)
C5B'0.075 (3)0.092 (2)0.071 (2)0.017 (2)0.030 (2)0.0012 (19)
C6B'0.066 (2)0.0510 (16)0.082 (3)0.0099 (14)0.0278 (19)0.0009 (15)
O1B'0.0697 (18)0.0479 (12)0.0854 (19)0.0094 (12)0.0343 (14)0.0235 (14)
O2B'0.073 (2)0.0426 (10)0.1008 (17)0.0110 (10)0.0473 (16)0.0147 (11)
P01A0.0442 (4)0.0436 (4)0.0500 (4)0.0020 (3)0.0107 (3)0.0105 (3)
O11A0.0593 (11)0.0432 (10)0.0705 (12)0.0049 (8)0.0115 (9)0.0128 (9)
C11A0.0425 (14)0.0444 (15)0.0454 (15)0.0083 (11)0.0142 (11)0.0081 (12)
C12A0.0550 (16)0.0562 (17)0.0537 (17)0.0114 (13)0.0178 (14)0.0135 (14)
C13A0.0681 (19)0.084 (2)0.0533 (18)0.0229 (17)0.0171 (16)0.0214 (16)
C14A0.0487 (17)0.097 (2)0.0560 (19)0.0179 (17)0.0018 (14)0.0035 (18)
C15A0.0434 (16)0.0698 (19)0.075 (2)0.0007 (14)0.0031 (15)0.0054 (17)
C16A0.0444 (15)0.0561 (16)0.0579 (17)0.0051 (13)0.0103 (13)0.0154 (13)
C21A0.0504 (15)0.0458 (15)0.0462 (15)0.0021 (12)0.0095 (12)0.0035 (12)
C22A0.103 (2)0.081 (2)0.074 (2)0.0353 (19)0.0450 (19)0.0201 (17)
C23A0.115 (3)0.097 (3)0.092 (3)0.023 (2)0.061 (2)0.001 (2)
C24A0.109 (3)0.097 (3)0.058 (2)0.018 (2)0.037 (2)0.0030 (19)
C25A0.104 (3)0.113 (3)0.071 (2)0.008 (2)0.032 (2)0.039 (2)
C26A0.074 (2)0.087 (2)0.0648 (19)0.0091 (17)0.0266 (16)0.0282 (17)
C31A0.0460 (15)0.0468 (15)0.0426 (14)0.0041 (12)0.0102 (11)0.0134 (12)
C32A0.0476 (16)0.0631 (18)0.0625 (18)0.0018 (14)0.0120 (13)0.0195 (14)
C33A0.0449 (16)0.092 (2)0.078 (2)0.0081 (17)0.0155 (14)0.0329 (18)
C34A0.067 (2)0.084 (2)0.075 (2)0.0344 (18)0.0295 (16)0.0334 (18)
C35A0.074 (2)0.0550 (18)0.086 (2)0.0179 (16)0.0202 (17)0.0120 (15)
C36A0.0501 (16)0.0554 (18)0.0748 (19)0.0082 (14)0.0119 (14)0.0101 (15)
P01B0.0458 (4)0.0424 (4)0.0492 (4)0.0041 (3)0.0135 (3)0.0100 (3)
O11B0.0649 (11)0.0435 (10)0.0701 (12)0.0124 (8)0.0249 (9)0.0131 (9)
C11B0.0360 (13)0.0427 (14)0.0466 (15)0.0042 (11)0.0078 (11)0.0074 (12)
C12B0.0446 (14)0.0624 (17)0.0510 (16)0.0022 (12)0.0077 (13)0.0146 (14)
C13B0.0540 (17)0.102 (2)0.0501 (18)0.0129 (17)0.0066 (14)0.0204 (16)
C14B0.0583 (19)0.106 (3)0.059 (2)0.0127 (18)0.0236 (15)0.0004 (19)
C15B0.0531 (17)0.071 (2)0.078 (2)0.0049 (14)0.0298 (16)0.0010 (17)
C16B0.0452 (15)0.0525 (16)0.0617 (17)0.0018 (13)0.0146 (13)0.0108 (13)
C21B0.0542 (16)0.0462 (15)0.0463 (15)0.0041 (13)0.0129 (12)0.0040 (13)
C22B0.089 (2)0.087 (2)0.074 (2)0.0309 (19)0.0104 (19)0.0227 (18)
C23B0.088 (2)0.106 (3)0.089 (3)0.033 (2)0.027 (2)0.011 (2)
C24B0.092 (3)0.088 (2)0.056 (2)0.015 (2)0.0110 (18)0.0053 (18)
C25B0.094 (3)0.108 (3)0.071 (2)0.003 (2)0.000 (2)0.0405 (19)
C26B0.0642 (18)0.087 (2)0.0663 (19)0.0026 (16)0.0000 (15)0.0298 (17)
C31B0.0438 (14)0.0507 (16)0.0462 (15)0.0039 (12)0.0124 (12)0.0163 (12)
C32B0.0509 (16)0.0687 (19)0.0611 (17)0.0079 (14)0.0170 (14)0.0209 (14)
C33B0.0459 (17)0.101 (3)0.080 (2)0.0086 (17)0.0197 (15)0.0368 (19)
C34B0.0549 (19)0.089 (3)0.084 (2)0.0181 (18)0.0043 (16)0.0392 (19)
C35B0.071 (2)0.062 (2)0.093 (2)0.0127 (17)0.0161 (18)0.0122 (17)
C36B0.0547 (17)0.0577 (18)0.078 (2)0.0022 (14)0.0209 (15)0.0074 (15)
Geometric parameters (Å, º) top
C1A—O1A1.436 (3)C6B'—H6B40.9700
C1A—C2A1.502 (3)O1B'—H1B20.8200
C1A—C6A1.506 (4)O2B'—H2B20.8200
C1A—H1A0.9800P01A—O11A1.4826 (16)
C2A—O2A1.446 (3)P01A—C21A1.794 (2)
C2A—C3A1.515 (4)P01A—C11A1.801 (2)
C2A—H2A0.9800P01A—C31A1.802 (2)
C3A—C4A1.522 (4)C11A—C16A1.386 (3)
C3A—H3A10.9700C11A—C12A1.390 (3)
C3A—H3A20.9700C12A—C13A1.381 (3)
C4A—C5A1.517 (4)C12A—H12A0.9300
C4A—H4A10.9700C13A—C14A1.365 (4)
C4A—H4A20.9700C13A—H13A0.9300
C5A—C6A1.509 (4)C14A—C15A1.370 (4)
C5A—H5A10.9700C14A—H14A0.9300
C5A—H5A20.9700C15A—C16A1.385 (3)
C6A—H6A10.9700C15A—H15A0.9300
C6A—H6A20.9700C16A—H16A0.9300
O1A—H1A10.8200C21A—C26A1.365 (3)
O2A—H2A10.8200C21A—C22A1.376 (3)
C1A'—O1A'1.437 (7)C22A—C23A1.387 (4)
C1A'—C2A'1.503 (6)C22A—H22A0.9300
C1A'—C6A'1.504 (7)C23A—C24A1.350 (4)
C1A'—H1A'0.9800C23A—H23A0.9300
C2A'—O2A'1.449 (6)C24A—C25A1.346 (4)
C2A'—C3A'1.517 (6)C24A—H24A0.9300
C2A'—H2A'0.9800C25A—C26A1.389 (4)
C3A'—C4A'1.524 (7)C25A—H25A0.9300
C3A'—H3A30.9700C26A—H26A0.9300
C3A'—H3A40.9700C31A—C32A1.381 (3)
C4A'—C5A'1.518 (6)C31A—C36A1.382 (3)
C4A'—H4A30.9700C32A—C33A1.382 (3)
C4A'—H4A40.9700C32A—H32A0.9300
C5A'—C6A'1.505 (6)C33A—C34A1.362 (4)
C5A'—H5A30.9700C33A—H33A0.9300
C5A'—H5A40.9700C34A—C35A1.370 (4)
C6A'—H6A30.9700C34A—H34A0.9300
C6A'—H6A40.9700C35A—C36A1.379 (3)
O1A'—H1A20.8200C35A—H35A0.9300
O2A'—H2A20.8200C36A—H36A0.9300
C1B—O1B1.437 (3)P01B—O11B1.4805 (16)
C1B—C6B1.504 (4)P01B—C21B1.797 (2)
C1B—C2B1.504 (3)P01B—C31B1.801 (2)
C1B—H1B0.9800P01B—C11B1.802 (2)
C2B—O2B1.427 (4)C11B—C12B1.389 (3)
C2B—C3B1.508 (4)C11B—C16B1.391 (3)
C2B—H2B0.9800C12B—C13B1.382 (3)
C3B—C4B1.527 (4)C12B—H12B0.9300
C3B—H3B10.9700C13B—C14B1.365 (4)
C3B—H3B20.9700C13B—H13B0.9300
C4B—C5B1.510 (4)C14B—C15B1.373 (4)
C4B—H4B10.9700C14B—H14B0.9300
C4B—H4B20.9700C15B—C16B1.387 (3)
C5B—C6B1.509 (4)C15B—H15B0.9300
C5B—H5B10.9700C16B—H16B0.9300
C5B—H5B20.9700C21B—C26B1.367 (3)
C6B—H6B10.9700C21B—C22B1.378 (3)
C6B—H6B20.9700C22B—C23B1.391 (4)
O1B—H1B10.8200C22B—H22B0.9300
O2B—H2B10.8200C23B—C24B1.347 (4)
C1B'—O1B'1.436 (7)C23B—H23B0.9300
C1B'—C6B'1.504 (7)C24B—C25B1.355 (4)
C1B'—C2B'1.506 (6)C24B—H24B0.9300
C1B'—H1B'0.9800C25B—C26B1.386 (4)
C2B'—O2B'1.428 (8)C25B—H25B0.9300
C2B'—C3B'1.509 (6)C26B—H26B0.9300
C2B'—H2B'0.9800C31B—C36B1.380 (3)
C3B'—C4B'1.526 (7)C31B—C32B1.384 (3)
C3B'—H3B30.9700C32B—C33B1.385 (4)
C3B'—H3B40.9700C32B—H32B0.9300
C4B'—C5B'1.509 (6)C33B—C34B1.361 (4)
C4B'—H4B30.9700C33B—H33B0.9300
C4B'—H4B40.9700C34B—C35B1.362 (4)
C5B'—C6B'1.508 (6)C34B—H34B0.9300
C5B'—H5B30.9700C35B—C36B1.380 (3)
C5B'—H5B40.9700C35B—H35B0.9300
C6B'—H6B30.9700C36B—H36B0.9300
O1A—C1A—C2A107.5 (3)C6B'—C5B'—C4B'110.7 (8)
O1A—C1A—C6A112.0 (3)C6B'—C5B'—H5B3109.5
C2A—C1A—C6A111.3 (3)C4B'—C5B'—H5B3109.5
O1A—C1A—H1A108.6C6B'—C5B'—H5B4109.5
C2A—C1A—H1A108.6C4B'—C5B'—H5B4109.5
C6A—C1A—H1A108.6H5B3—C5B'—H5B4108.1
O2A—C2A—C1A110.2 (3)C1B'—C6B'—C5B'111.0 (9)
O2A—C2A—C3A107.8 (3)C1B'—C6B'—H6B3109.4
C1A—C2A—C3A110.2 (3)C5B'—C6B'—H6B3109.4
O2A—C2A—H2A109.6C1B'—C6B'—H6B4109.4
C1A—C2A—H2A109.6C5B'—C6B'—H6B4109.4
C3A—C2A—H2A109.6H6B3—C6B'—H6B4108.0
C2A—C3A—C4A111.0 (3)C1B'—O1B'—H1B2109.5
C2A—C3A—H3A1109.4C2B'—O2B'—H2B2109.5
C4A—C3A—H3A1109.4O11A—P01A—C21A113.68 (10)
C2A—C3A—H3A2109.4O11A—P01A—C11A112.01 (10)
C4A—C3A—H3A2109.4C21A—P01A—C11A105.80 (11)
H3A1—C3A—H3A2108.0O11A—P01A—C31A111.60 (10)
C5A—C4A—C3A111.2 (3)C21A—P01A—C31A106.76 (11)
C5A—C4A—H4A1109.4C11A—P01A—C31A106.50 (10)
C3A—C4A—H4A1109.4C16A—C11A—C12A119.0 (2)
C5A—C4A—H4A2109.4C16A—C11A—P01A123.67 (18)
C3A—C4A—H4A2109.4C12A—C11A—P01A117.31 (18)
H4A1—C4A—H4A2108.0C13A—C12A—C11A120.4 (2)
C6A—C5A—C4A110.1 (3)C13A—C12A—H12A119.8
C6A—C5A—H5A1109.6C11A—C12A—H12A119.8
C4A—C5A—H5A1109.6C14A—C13A—C12A120.1 (3)
C6A—C5A—H5A2109.6C14A—C13A—H13A120.0
C4A—C5A—H5A2109.6C12A—C13A—H13A120.0
H5A1—C5A—H5A2108.1C13A—C14A—C15A120.3 (3)
C1A—C6A—C5A111.9 (3)C13A—C14A—H14A119.9
C1A—C6A—H6A1109.2C15A—C14A—H14A119.9
C5A—C6A—H6A1109.2C14A—C15A—C16A120.5 (3)
C1A—C6A—H6A2109.2C14A—C15A—H15A119.8
C5A—C6A—H6A2109.2C16A—C15A—H15A119.8
H6A1—C6A—H6A2107.9C15A—C16A—C11A119.7 (2)
O1A'—C1A'—C2A'107.6 (8)C15A—C16A—H16A120.1
O1A'—C1A'—C6A'111.6 (9)C11A—C16A—H16A120.1
C2A'—C1A'—C6A'112.7 (8)C26A—C21A—C22A117.6 (2)
O1A'—C1A'—H1A'108.2C26A—C21A—P01A123.5 (2)
C2A'—C1A'—H1A'108.2C22A—C21A—P01A118.9 (2)
C6A'—C1A'—H1A'108.2C21A—C22A—C23A120.6 (3)
O2A'—C2A'—C1A'109.2 (8)C21A—C22A—H22A119.7
O2A'—C2A'—C3A'106.5 (8)C23A—C22A—H22A119.7
C1A'—C2A'—C3A'110.9 (8)C24A—C23A—C22A120.8 (3)
O2A'—C2A'—H2A'110.1C24A—C23A—H23A119.6
C1A'—C2A'—H2A'110.1C22A—C23A—H23A119.6
C3A'—C2A'—H2A'110.1C25A—C24A—C23A119.4 (3)
C2A'—C3A'—C4A'110.6 (8)C25A—C24A—H24A120.3
C2A'—C3A'—H3A3109.5C23A—C24A—H24A120.3
C4A'—C3A'—H3A3109.5C24A—C25A—C26A120.4 (3)
C2A'—C3A'—H3A4109.5C24A—C25A—H25A119.8
C4A'—C3A'—H3A4109.5C26A—C25A—H25A119.8
H3A3—C3A'—H3A4108.1C21A—C26A—C25A121.2 (3)
C5A'—C4A'—C3A'109.8 (8)C21A—C26A—H26A119.4
C5A'—C4A'—H4A3109.7C25A—C26A—H26A119.4
C3A'—C4A'—H4A3109.7C32A—C31A—C36A118.1 (2)
C5A'—C4A'—H4A4109.7C32A—C31A—P01A118.24 (19)
C3A'—C4A'—H4A4109.7C36A—C31A—P01A123.68 (19)
H4A3—C4A'—H4A4108.2C31A—C32A—C33A120.9 (3)
C6A'—C5A'—C4A'109.9 (8)C31A—C32A—H32A119.6
C6A'—C5A'—H5A3109.7C33A—C32A—H32A119.6
C4A'—C5A'—H5A3109.7C34A—C33A—C32A120.0 (3)
C6A'—C5A'—H5A4109.7C34A—C33A—H33A120.0
C4A'—C5A'—H5A4109.7C32A—C33A—H33A120.0
H5A3—C5A'—H5A4108.2C33A—C34A—C35A120.2 (3)
C1A'—C6A'—C5A'112.1 (9)C33A—C34A—H34A119.9
C1A'—C6A'—H6A3109.2C35A—C34A—H34A119.9
C5A'—C6A'—H6A3109.2C34A—C35A—C36A119.9 (3)
C1A'—C6A'—H6A4109.2C34A—C35A—H35A120.1
C5A'—C6A'—H6A4109.2C36A—C35A—H35A120.1
H6A3—C6A'—H6A4107.9C35A—C36A—C31A121.0 (2)
C1A'—O1A'—H1A2109.5C35A—C36A—H36A119.5
C2A'—O2A'—H2A2109.5C31A—C36A—H36A119.5
O1B—C1B—C6B108.4 (3)O11B—P01B—C21B113.54 (11)
O1B—C1B—C2B110.8 (3)O11B—P01B—C31B111.65 (11)
C6B—C1B—C2B111.2 (3)C21B—P01B—C31B106.69 (11)
O1B—C1B—H1B108.8O11B—P01B—C11B111.80 (10)
C6B—C1B—H1B108.8C21B—P01B—C11B105.91 (11)
C2B—C1B—H1B108.8C31B—P01B—C11B106.80 (11)
O2B—C2B—C1B108.1 (3)C12B—C11B—C16B119.3 (2)
O2B—C2B—C3B111.9 (4)C12B—C11B—P01B117.31 (18)
C1B—C2B—C3B110.7 (3)C16B—C11B—P01B123.40 (18)
O2B—C2B—H2B108.7C13B—C12B—C11B120.2 (2)
C1B—C2B—H2B108.7C13B—C12B—H12B119.9
C3B—C2B—H2B108.7C11B—C12B—H12B119.9
C2B—C3B—C4B110.7 (3)C14B—C13B—C12B120.2 (3)
C2B—C3B—H3B1109.5C14B—C13B—H13B119.9
C4B—C3B—H3B1109.5C12B—C13B—H13B119.9
C2B—C3B—H3B2109.5C13B—C14B—C15B120.3 (3)
C4B—C3B—H3B2109.5C13B—C14B—H14B119.9
H3B1—C3B—H3B2108.1C15B—C14B—H14B119.9
C5B—C4B—C3B110.8 (3)C14B—C15B—C16B120.5 (3)
C5B—C4B—H4B1109.5C14B—C15B—H15B119.8
C3B—C4B—H4B1109.5C16B—C15B—H15B119.8
C5B—C4B—H4B2109.5C15B—C16B—C11B119.5 (2)
C3B—C4B—H4B2109.5C15B—C16B—H16B120.3
H4B1—C4B—H4B2108.1C11B—C16B—H16B120.3
C6B—C5B—C4B111.1 (3)C26B—C21B—C22B117.8 (2)
C6B—C5B—H5B1109.4C26B—C21B—P01B123.5 (2)
C4B—C5B—H5B1109.4C22B—C21B—P01B118.7 (2)
C6B—C5B—H5B2109.4C21B—C22B—C23B120.6 (3)
C4B—C5B—H5B2109.4C21B—C22B—H22B119.7
H5B1—C5B—H5B2108.0C23B—C22B—H22B119.7
C1B—C6B—C5B111.7 (3)C24B—C23B—C22B120.5 (3)
C1B—C6B—H6B1109.3C24B—C23B—H23B119.8
C5B—C6B—H6B1109.3C22B—C23B—H23B119.8
C1B—C6B—H6B2109.3C23B—C24B—C25B119.6 (3)
C5B—C6B—H6B2109.3C23B—C24B—H24B120.2
H6B1—C6B—H6B2107.9C25B—C24B—H24B120.2
O1B'—C1B'—C6B'108.4 (9)C24B—C25B—C26B120.6 (3)
O1B'—C1B'—C2B'111.0 (9)C24B—C25B—H25B119.7
C6B'—C1B'—C2B'111.5 (9)C26B—C25B—H25B119.7
O1B'—C1B'—H1B'108.6C21B—C26B—C25B120.9 (3)
C6B'—C1B'—H1B'108.6C21B—C26B—H26B119.6
C2B'—C1B'—H1B'108.6C25B—C26B—H26B119.6
O2B'—C2B'—C1B'108.0 (10)C36B—C31B—C32B118.1 (2)
O2B'—C2B'—C3B'111.8 (10)C36B—C31B—P01B123.74 (19)
C1B'—C2B'—C3B'111.1 (8)C32B—C31B—P01B118.2 (2)
O2B'—C2B'—H2B'108.6C31B—C32B—C33B120.7 (3)
C1B'—C2B'—H2B'108.6C31B—C32B—H32B119.7
C3B'—C2B'—H2B'108.6C33B—C32B—H32B119.7
C2B'—C3B'—C4B'111.0 (9)C34B—C33B—C32B119.9 (3)
C2B'—C3B'—H3B3109.4C34B—C33B—H33B120.0
C4B'—C3B'—H3B3109.4C32B—C33B—H33B120.0
C2B'—C3B'—H3B4109.4C33B—C34B—C35B120.4 (3)
C4B'—C3B'—H3B4109.4C33B—C34B—H34B119.8
H3B3—C3B'—H3B4108.0C35B—C34B—H34B119.8
C5B'—C4B'—C3B'110.9 (9)C34B—C35B—C36B119.9 (3)
C5B'—C4B'—H4B3109.5C34B—C35B—H35B120.0
C3B'—C4B'—H4B3109.5C36B—C35B—H35B120.0
C5B'—C4B'—H4B4109.5C31B—C36B—C35B121.0 (3)
C3B'—C4B'—H4B4109.5C31B—C36B—H36B119.5
H4B3—C4B'—H4B4108.1C35B—C36B—H36B119.5
O1A—C1A—C2A—O2A61.4 (5)C26A—C21A—C22A—C23A0.7 (4)
C6A—C1A—C2A—O2A175.5 (3)P01A—C21A—C22A—C23A176.3 (2)
O1A—C1A—C2A—C3A179.8 (3)C21A—C22A—C23A—C24A0.7 (5)
C6A—C1A—C2A—C3A56.7 (6)C22A—C23A—C24A—C25A2.0 (5)
O2A—C2A—C3A—C4A176.8 (3)C23A—C24A—C25A—C26A1.9 (5)
C1A—C2A—C3A—C4A56.6 (6)C22A—C21A—C26A—C25A0.7 (4)
C2A—C3A—C4A—C5A56.3 (6)P01A—C21A—C26A—C25A176.1 (2)
C3A—C4A—C5A—C6A55.0 (7)C24A—C25A—C26A—C21A0.6 (5)
O1A—C1A—C6A—C5A177.4 (3)O11A—P01A—C31A—C32A20.3 (2)
C2A—C1A—C6A—C5A56.9 (7)C21A—P01A—C31A—C32A104.47 (19)
C4A—C5A—C6A—C1A55.4 (8)C11A—P01A—C31A—C32A142.84 (19)
O1A'—C1A'—C2A'—O2A'66.8 (16)O11A—P01A—C31A—C36A158.01 (19)
C6A'—C1A'—C2A'—O2A'169.7 (16)C21A—P01A—C31A—C36A77.2 (2)
O1A'—C1A'—C2A'—C3A'176.2 (15)C11A—P01A—C31A—C36A35.5 (2)
C6A'—C1A'—C2A'—C3A'52.7 (18)C36A—C31A—C32A—C33A0.9 (4)
O2A'—C2A'—C3A'—C4A'174.2 (16)P01A—C31A—C32A—C33A177.54 (19)
C1A'—C2A'—C3A'—C4A'55.5 (17)C31A—C32A—C33A—C34A0.4 (4)
C2A'—C3A'—C4A'—C5A'59 (2)C32A—C33A—C34A—C35A0.7 (4)
C3A'—C4A'—C5A'—C6A'58.8 (16)C33A—C34A—C35A—C36A1.3 (4)
O1A'—C1A'—C6A'—C5A'174.7 (19)C34A—C35A—C36A—C31A0.8 (4)
C2A'—C1A'—C6A'—C5A'53 (2)C32A—C31A—C36A—C35A0.2 (4)
C4A'—C5A'—C6A'—C1A'56 (2)P01A—C31A—C36A—C35A178.1 (2)
O1B—C1B—C2B—O2B59.7 (6)O11B—P01B—C11B—C12B22.5 (2)
C6B—C1B—C2B—O2B179.6 (3)C21B—P01B—C11B—C12B146.62 (18)
O1B—C1B—C2B—C3B177.4 (2)C31B—P01B—C11B—C12B99.92 (19)
C6B—C1B—C2B—C3B56.7 (6)O11B—P01B—C11B—C16B158.70 (18)
O2B—C2B—C3B—C4B177.7 (3)C21B—P01B—C11B—C16B34.6 (2)
C1B—C2B—C3B—C4B57.0 (6)C31B—P01B—C11B—C16B78.9 (2)
C2B—C3B—C4B—C5B56.3 (7)C16B—C11B—C12B—C13B0.8 (3)
C3B—C4B—C5B—C6B55.0 (7)P01B—C11B—C12B—C13B178.08 (18)
O1B—C1B—C6B—C5B177.8 (3)C11B—C12B—C13B—C14B0.4 (4)
C2B—C1B—C6B—C5B55.7 (6)C12B—C13B—C14B—C15B1.2 (4)
C4B—C5B—C6B—C1B54.9 (7)C13B—C14B—C15B—C16B0.9 (4)
O1B'—C1B'—C2B'—O2B'60 (2)C14B—C15B—C16B—C11B0.3 (4)
C6B'—C1B'—C2B'—O2B'179 (2)C12B—C11B—C16B—C15B1.1 (3)
O1B'—C1B'—C2B'—C3B'176.6 (17)P01B—C11B—C16B—C15B177.69 (18)
C6B'—C1B'—C2B'—C3B'55.6 (18)O11B—P01B—C21B—C26B115.2 (2)
O2B'—C2B'—C3B'—C4B'176 (2)C31B—P01B—C21B—C26B8.2 (3)
C1B'—C2B'—C3B'—C4B'55 (2)C11B—P01B—C21B—C26B121.7 (2)
C2B'—C3B'—C4B'—C5B'56 (2)O11B—P01B—C21B—C22B62.0 (2)
C3B'—C4B'—C5B'—C6B'56.3 (19)C31B—P01B—C21B—C22B174.6 (2)
O1B'—C1B'—C6B'—C5B'179 (2)C11B—P01B—C21B—C22B61.1 (2)
C2B'—C1B'—C6B'—C5B'57 (2)C26B—C21B—C22B—C23B1.0 (5)
C4B'—C5B'—C6B'—C1B'56.9 (19)P01B—C21B—C22B—C23B176.4 (3)
O11A—P01A—C11A—C16A158.04 (18)C21B—C22B—C23B—C24B0.1 (5)
C21A—P01A—C11A—C16A33.7 (2)C22B—C23B—C24B—C25B1.2 (6)
C31A—P01A—C11A—C16A79.7 (2)C23B—C24B—C25B—C26B1.1 (5)
O11A—P01A—C11A—C12A23.3 (2)C22B—C21B—C26B—C25B1.1 (4)
C21A—P01A—C11A—C12A147.66 (18)P01B—C21B—C26B—C25B176.2 (2)
C31A—P01A—C11A—C12A98.99 (19)C24B—C25B—C26B—C21B0.0 (5)
C16A—C11A—C12A—C13A1.0 (3)O11B—P01B—C31B—C36B156.4 (2)
P01A—C11A—C12A—C13A177.70 (18)C21B—P01B—C31B—C36B79.0 (2)
C11A—C12A—C13A—C14A0.1 (4)C11B—P01B—C31B—C36B33.9 (2)
C12A—C13A—C14A—C15A0.8 (4)O11B—P01B—C31B—C32B23.2 (2)
C13A—C14A—C15A—C16A0.4 (4)C21B—P01B—C31B—C32B101.37 (19)
C14A—C15A—C16A—C11A0.8 (4)C11B—P01B—C31B—C32B145.71 (18)
C12A—C11A—C16A—C15A1.5 (3)C36B—C31B—C32B—C33B1.3 (4)
P01A—C11A—C16A—C15A177.18 (18)P01B—C31B—C32B—C33B178.3 (2)
O11A—P01A—C21A—C26A114.4 (2)C31B—C32B—C33B—C34B0.9 (4)
C11A—P01A—C21A—C26A122.3 (2)C32B—C33B—C34B—C35B0.2 (4)
C31A—P01A—C21A—C26A9.1 (3)C33B—C34B—C35B—C36B0.8 (4)
O11A—P01A—C21A—C22A62.3 (2)C32B—C31B—C36B—C35B0.6 (4)
C11A—P01A—C21A—C22A61.0 (2)P01B—C31B—C36B—C35B179.0 (2)
C31A—P01A—C21A—C22A174.2 (2)C34B—C35B—C36B—C31B0.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A1···O1Bi0.821.972.772 (4)167
O2A—H2A1···O1Aii0.821.962.742 (4)160
O1B—H1B1···O2Bi0.822.032.793 (5)155
O2B—H2B1···O2Aii0.821.962.772 (5)174
O1A—H1A2···O2Aii0.822.132.76 (3)133
O2A—H2A2···O2Bii0.821.942.73 (4)163
O1B—H1B2···O1Ai0.822.082.84 (3)154
O2B—H2B2···O1Bi0.821.882.59 (6)144
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.
(ethanol294Ktri) 1:1 rac-1,2-cyclohexanediol triphenylphosphine oxide top
Crystal data top
C6H12O2·C18H15OPZ = 4
Mr = 394.43F(000) = 840
Triclinic, P1Dx = 1.232 Mg m3
a = 9.348 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.997 (2) ÅCell parameters from 9631 reflections
c = 21.556 (3) Åθ = 1.0–27.5°
α = 100.21 (1)°µ = 0.15 mm1
β = 102.49 (1)°T = 294 K
γ = 90.24 (1)°Lath, colorless
V = 2127.2 (7) Å30.25 × 0.15 × 0.15 mm
Data collection top
Nonius KappaCCD
diffractometer
7473 independent reflections
Radiation source: fine-focus sealed tube4988 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.035
Detector resolution: 10 pixels mm-1θmax = 25.0°, θmin = 1.9°
1.0° ω scans at fixed χ = 55°h = 1111
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
k = 1313
Tmin = 0.96, Tmax = 0.98l = 2525
14890 measured 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)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.118H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0587P)2 + 0.1303P]
where P = (Fo2 + 2Fc2)/3
7473 reflections(Δ/σ)max = 0.001
564 parametersΔρmax = 0.18 e Å3
148 restraintsΔρmin = 0.21 e Å3
Crystal data top
C6H12O2·C18H15OPγ = 90.24 (1)°
Mr = 394.43V = 2127.2 (7) Å3
Triclinic, P1Z = 4
a = 9.348 (2) ÅMo Kα radiation
b = 10.997 (2) ŵ = 0.15 mm1
c = 21.556 (3) ÅT = 294 K
α = 100.21 (1)°0.25 × 0.15 × 0.15 mm
β = 102.49 (1)°
Data collection top
Nonius KappaCCD
diffractometer
7473 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
4988 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.98Rint = 0.035
14890 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.044148 restraints
wR(F2) = 0.118H-atom parameters constrained
S = 1.03Δρmax = 0.18 e Å3
7473 reflectionsΔρmin = 0.21 e Å3
564 parameters
Special details top

Experimental. The crystal-to-detector distance was 43 mm. Each frame was measured for 75 s. The number of scan sets measured was 9; the total number of frames measured was 987.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.7758 (4)0.0747 (3)0.0372 (2)0.0485 (11)0.778 (6)
H1A0.82580.05610.00130.058*0.778 (6)
C2A0.7453 (4)0.0439 (3)0.0581 (2)0.0518 (13)0.778 (6)
H2A0.68930.02690.09200.062*0.778 (6)
C3A0.8871 (6)0.1012 (4)0.0842 (3)0.0704 (17)0.778 (6)
H3A10.93880.12500.04970.085*0.778 (6)
H3A20.86570.17530.09980.085*0.778 (6)
C4A0.9846 (6)0.0112 (5)0.1391 (3)0.0820 (18)0.778 (6)
H4A10.93720.00560.17540.098*0.778 (6)
H4A21.07690.04860.15320.098*0.778 (6)
C5A1.0139 (5)0.1087 (4)0.1181 (2)0.0758 (14)0.778 (6)
H5A11.06960.16640.15480.091*0.778 (6)
H5A21.07190.09350.08550.091*0.778 (6)
C6A0.8724 (7)0.1643 (4)0.0912 (4)0.0671 (11)0.778 (6)
H6A10.89380.23780.07510.080*0.778 (6)
H6A20.82030.18890.12540.080*0.778 (6)
O1A0.6369 (4)0.1250 (4)0.0142 (2)0.0633 (12)0.778 (6)
H1A10.65020.19530.00810.095*0.778 (6)
O2A0.6615 (5)0.1307 (4)0.0043 (3)0.0682 (15)0.778 (6)
H2A10.57570.11120.00310.102*0.778 (6)
C1A'0.7438 (14)0.0803 (11)0.0561 (6)0.0485 (11)0.222 (6)
H1A'0.67840.09010.08640.058*0.222 (6)
C2A'0.7727 (15)0.0542 (11)0.0400 (7)0.0518 (13)0.222 (6)
H2A'0.82560.06720.00490.062*0.222 (6)
C3A'0.863 (2)0.0992 (13)0.0981 (10)0.0704 (17)0.222 (6)
H3A30.88390.18530.08590.085*0.222 (6)
H3A40.80740.09310.13160.085*0.222 (6)
C4A'1.0061 (17)0.0219 (15)0.1238 (11)0.0820 (18)0.222 (6)
H4A31.06340.05140.16090.098*0.222 (6)
H4A41.06310.02990.09080.098*0.222 (6)
C5A'0.9731 (17)0.1123 (14)0.1431 (7)0.0758 (14)0.222 (6)
H5A30.92160.12060.17800.091*0.222 (6)
H5A41.06440.16160.15850.091*0.222 (6)
C6A'0.881 (2)0.1594 (13)0.0869 (13)0.0671 (11)0.222 (6)
H6A30.93890.16240.05480.080*0.222 (6)
H6A40.85450.24300.10150.080*0.222 (6)
O1A'0.6690 (17)0.1187 (16)0.0024 (7)0.0633 (12)0.222 (6)
H1A20.58180.09770.01000.095*0.222 (6)
O2A'0.6363 (18)0.1269 (16)0.0198 (11)0.0682 (15)0.222 (6)
H2A20.65310.20030.01910.102*0.222 (6)
C1B0.3094 (5)0.5859 (3)0.0530 (2)0.0512 (11)0.858 (7)
H1B0.40290.59960.08480.061*0.858 (7)
C2B0.2675 (5)0.4510 (3)0.0391 (2)0.0514 (11)0.858 (7)
H2B0.17630.43690.00580.062*0.858 (7)
C3B0.2414 (7)0.4078 (4)0.0985 (3)0.0794 (16)0.858 (7)
H3B10.33240.41620.13100.095*0.858 (7)
H3B20.20980.32100.08750.095*0.858 (7)
C4B0.1246 (7)0.4831 (5)0.1260 (3)0.0888 (18)0.858 (7)
H4B10.03080.46730.09540.107*0.858 (7)
H4B20.11450.45780.16570.107*0.858 (7)
C5B0.1659 (6)0.6196 (4)0.1392 (2)0.0826 (14)0.858 (7)
H5B10.08650.66590.15280.099*0.858 (7)
H5B20.25220.63690.17420.099*0.858 (7)
C6B0.1967 (8)0.6612 (4)0.0806 (3)0.0682 (13)0.858 (7)
H6B10.10640.65520.04780.082*0.858 (7)
H6B20.23100.74730.09200.082*0.858 (7)
O1B0.3276 (4)0.6277 (4)0.00438 (19)0.0673 (11)0.858 (7)
H1B10.40380.60190.01380.101*0.858 (7)
O2B0.3798 (10)0.3853 (4)0.0139 (4)0.0715 (14)0.858 (7)
H2B10.35920.31090.00690.107*0.858 (7)
C1B'0.265 (2)0.5758 (17)0.0374 (9)0.0512 (11)0.142 (7)
H1B'0.18150.55310.00080.061*0.142 (7)
C2B'0.321 (2)0.4605 (17)0.0604 (11)0.0514 (11)0.142 (7)
H2B'0.40970.48240.09450.062*0.142 (7)
C3B'0.209 (4)0.4002 (19)0.0877 (17)0.0794 (16)0.142 (7)
H3B30.25150.33000.10550.095*0.142 (7)
H3B40.12470.36990.05330.095*0.142 (7)
C4B'0.160 (4)0.491 (3)0.1406 (14)0.0888 (18)0.142 (7)
H4B30.08260.45220.15480.107*0.142 (7)
H4B40.24180.51320.17750.107*0.142 (7)
C5B'0.105 (3)0.607 (3)0.1165 (13)0.0826 (14)0.142 (7)
H5B30.01560.58650.08350.099*0.142 (7)
H5B40.08220.66550.15190.099*0.142 (7)
C6B'0.217 (4)0.6650 (18)0.0892 (17)0.0682 (13)0.142 (7)
H6B30.30130.69500.12360.082*0.142 (7)
H6B40.17540.73540.07130.082*0.142 (7)
O1B'0.378 (2)0.636 (2)0.0160 (11)0.0673 (11)0.142 (7)
H1B20.34000.68470.00700.101*0.142 (7)
O2B'0.359 (6)0.380 (2)0.007 (2)0.0715 (14)0.142 (7)
H2B20.42180.41400.00540.107*0.142 (7)
P01A0.78759 (8)0.16287 (7)0.33613 (4)0.0452 (2)
O11A0.8450 (2)0.29092 (17)0.34091 (9)0.0595 (6)
C11A0.6336 (3)0.1201 (3)0.26860 (12)0.0435 (7)
C12A0.6209 (3)0.1843 (3)0.21794 (14)0.0543 (8)
H12A0.68840.24840.22040.065*
C13A0.5084 (4)0.1534 (3)0.16369 (15)0.0678 (10)
H13A0.49990.19660.12980.081*
C14A0.4096 (4)0.0589 (4)0.16010 (17)0.0728 (11)
H14A0.33460.03780.12340.087*
C15A0.4196 (3)0.0048 (3)0.20980 (16)0.0659 (9)
H15A0.35150.06870.20670.079*
C16A0.5311 (3)0.0255 (3)0.26473 (14)0.0523 (8)
H16A0.53730.01710.29870.063*
C21A0.7252 (3)0.1380 (3)0.40633 (13)0.0486 (7)
C22A0.6090 (4)0.2033 (3)0.42263 (17)0.0806 (11)
H22A0.56100.25520.39600.097*
C23A0.5634 (5)0.1921 (4)0.4783 (2)0.0983 (14)
H23A0.48470.23640.48870.118*
C24A0.6318 (5)0.1175 (4)0.51793 (18)0.0838 (12)
H24A0.60210.11220.55590.101*
C25A0.7434 (5)0.0510 (4)0.50189 (19)0.0917 (12)
H25A0.78880.00230.52830.110*
C26A0.7912 (4)0.0614 (3)0.44621 (15)0.0721 (10)
H26A0.86900.01550.43600.086*
C31A0.9248 (3)0.0520 (3)0.32448 (13)0.0445 (7)
C32A1.0706 (3)0.0935 (3)0.34228 (14)0.0569 (8)
H32A1.09500.17590.36100.068*
C33A1.1803 (4)0.0126 (4)0.33226 (16)0.0689 (10)
H33A1.27790.04120.34410.083*
C34A1.1460 (4)0.1082 (4)0.30523 (16)0.0727 (10)
H34A1.21990.16160.29800.087*
C35A1.0030 (4)0.1511 (3)0.28879 (16)0.0716 (10)
H35A0.98000.23430.27140.086*
C36A0.8927 (4)0.0718 (3)0.29779 (15)0.0606 (9)
H36A0.79550.10170.28580.073*
P01B0.54897 (8)0.66169 (7)0.33429 (4)0.0449 (2)
O11B0.4982 (2)0.78930 (17)0.33949 (9)0.0574 (6)
C11B0.6378 (3)0.6210 (3)0.26757 (13)0.0436 (7)
C12B0.6040 (3)0.6879 (3)0.21755 (13)0.0532 (8)
H12B0.53990.75220.22010.064*
C13B0.6656 (4)0.6591 (4)0.16410 (15)0.0690 (10)
H13B0.64330.70430.13090.083*
C14B0.7589 (4)0.5643 (4)0.15997 (17)0.0755 (11)
H14B0.79840.54420.12360.091*
C15B0.7944 (3)0.4990 (3)0.20909 (16)0.0659 (9)
H15B0.85870.43510.20600.079*
C16B0.7353 (3)0.5270 (3)0.26353 (14)0.0540 (8)
H16B0.76120.48300.29700.065*
C21B0.6786 (3)0.6357 (3)0.40474 (13)0.0490 (8)
C22B0.8116 (4)0.7029 (3)0.42237 (17)0.0871 (12)
H22B0.83370.75600.39630.105*
C23B0.9121 (5)0.6915 (4)0.47851 (19)0.1020 (15)
H23B1.00080.73730.48990.122*
C24B0.8821 (5)0.6142 (4)0.51681 (18)0.0856 (12)
H24B0.94920.60780.55470.103*
C25B0.7544 (5)0.5465 (4)0.49979 (18)0.0921 (13)
H25B0.73410.49260.52580.111*
C26B0.6533 (4)0.5570 (3)0.44381 (15)0.0722 (10)
H26B0.56610.50920.43260.087*
C31B0.3987 (3)0.5493 (3)0.32142 (13)0.0469 (7)
C32B0.2717 (3)0.5886 (3)0.34054 (14)0.0559 (8)
H32B0.26710.67020.36060.067*
C33B0.1519 (4)0.5077 (4)0.33005 (16)0.0719 (10)
H33B0.06670.53550.34250.086*
C34B0.1580 (4)0.3873 (4)0.30156 (17)0.0743 (11)
H34B0.07720.33310.29460.089*
C35B0.2832 (4)0.3465 (3)0.28324 (17)0.0762 (10)
H35B0.28810.26430.26430.091*
C36B0.4026 (4)0.4277 (3)0.29287 (15)0.0635 (9)
H36B0.48700.39960.27980.076*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.041 (2)0.0486 (17)0.059 (3)0.0045 (14)0.0124 (17)0.0138 (17)
C2A0.047 (2)0.0489 (17)0.061 (3)0.0027 (15)0.0109 (19)0.0147 (17)
C3A0.052 (2)0.074 (2)0.093 (4)0.0090 (17)0.009 (2)0.041 (2)
C4A0.058 (3)0.112 (3)0.077 (4)0.004 (2)0.002 (2)0.041 (2)
C5A0.050 (3)0.099 (3)0.073 (3)0.011 (2)0.000 (2)0.018 (2)
C6A0.058 (2)0.058 (2)0.077 (2)0.0046 (15)0.0087 (17)0.0019 (16)
O1A0.046 (2)0.0492 (15)0.095 (3)0.0078 (14)0.0075 (16)0.0222 (19)
O2A0.053 (2)0.0499 (14)0.094 (3)0.0013 (14)0.0039 (19)0.0076 (17)
C1A'0.041 (2)0.0486 (17)0.059 (3)0.0045 (14)0.0124 (17)0.0138 (17)
C2A'0.047 (2)0.0489 (17)0.061 (3)0.0027 (15)0.0109 (19)0.0147 (17)
C3A'0.052 (2)0.074 (2)0.093 (4)0.0090 (17)0.009 (2)0.041 (2)
C4A'0.058 (3)0.112 (3)0.077 (4)0.004 (2)0.002 (2)0.041 (2)
C5A'0.050 (3)0.099 (3)0.073 (3)0.011 (2)0.000 (2)0.018 (2)
C6A'0.058 (2)0.058 (2)0.077 (2)0.0046 (15)0.0087 (17)0.0019 (16)
O1A'0.046 (2)0.0492 (15)0.095 (3)0.0078 (14)0.0075 (16)0.0222 (19)
O2A'0.053 (2)0.0499 (14)0.094 (3)0.0013 (14)0.0039 (19)0.0076 (17)
C1B0.047 (3)0.0482 (17)0.057 (2)0.0001 (16)0.0122 (19)0.0051 (16)
C2B0.050 (3)0.0490 (17)0.059 (3)0.0059 (16)0.020 (2)0.0122 (16)
C3B0.085 (4)0.082 (2)0.095 (3)0.024 (2)0.048 (3)0.045 (2)
C4B0.097 (4)0.105 (3)0.090 (4)0.025 (3)0.056 (3)0.040 (3)
C5B0.083 (4)0.099 (2)0.071 (3)0.020 (2)0.036 (3)0.007 (2)
C6B0.070 (3)0.055 (2)0.083 (3)0.0103 (18)0.032 (2)0.0037 (17)
O1B0.075 (3)0.0565 (17)0.084 (3)0.0066 (17)0.038 (2)0.0237 (18)
O2B0.080 (3)0.0480 (13)0.102 (3)0.0144 (15)0.051 (3)0.0153 (15)
C1B'0.047 (3)0.0482 (17)0.057 (2)0.0001 (16)0.0122 (19)0.0051 (16)
C2B'0.050 (3)0.0490 (17)0.059 (3)0.0059 (16)0.020 (2)0.0122 (16)
C3B'0.085 (4)0.082 (2)0.095 (3)0.024 (2)0.048 (3)0.045 (2)
C4B'0.097 (4)0.105 (3)0.090 (4)0.025 (3)0.056 (3)0.040 (3)
C5B'0.083 (4)0.099 (2)0.071 (3)0.020 (2)0.036 (3)0.007 (2)
C6B'0.070 (3)0.055 (2)0.083 (3)0.0103 (18)0.032 (2)0.0037 (17)
O1B'0.075 (3)0.0565 (17)0.084 (3)0.0066 (17)0.038 (2)0.0237 (18)
O2B'0.080 (3)0.0480 (13)0.102 (3)0.0144 (15)0.051 (3)0.0153 (15)
P01A0.0431 (4)0.0458 (5)0.0470 (5)0.0018 (4)0.0096 (4)0.0099 (4)
O11A0.0612 (14)0.0452 (13)0.0705 (14)0.0065 (10)0.0102 (11)0.0120 (10)
C11A0.0422 (17)0.0480 (19)0.0428 (17)0.0089 (14)0.0146 (14)0.0083 (14)
C12A0.055 (2)0.059 (2)0.053 (2)0.0115 (16)0.0187 (17)0.0129 (16)
C13A0.067 (2)0.093 (3)0.048 (2)0.022 (2)0.0160 (19)0.0231 (19)
C14A0.049 (2)0.103 (3)0.056 (2)0.019 (2)0.0007 (18)0.000 (2)
C15A0.0431 (19)0.071 (2)0.075 (2)0.0033 (17)0.0013 (19)0.006 (2)
C16A0.0429 (18)0.056 (2)0.059 (2)0.0040 (16)0.0094 (16)0.0159 (16)
C21A0.0502 (18)0.0490 (19)0.0434 (18)0.0037 (15)0.0077 (15)0.0031 (15)
C22A0.095 (3)0.083 (3)0.076 (3)0.030 (2)0.043 (2)0.017 (2)
C23A0.115 (4)0.100 (3)0.091 (3)0.021 (3)0.062 (3)0.001 (3)
C24A0.104 (3)0.096 (3)0.054 (2)0.015 (3)0.031 (2)0.005 (2)
C25A0.102 (3)0.112 (4)0.071 (3)0.006 (3)0.026 (3)0.037 (2)
C26A0.071 (2)0.092 (3)0.061 (2)0.010 (2)0.0230 (19)0.025 (2)
C31A0.0436 (18)0.0493 (19)0.0431 (17)0.0026 (14)0.0092 (14)0.0156 (14)
C32A0.050 (2)0.064 (2)0.060 (2)0.0040 (17)0.0125 (17)0.0197 (16)
C33A0.044 (2)0.096 (3)0.075 (2)0.010 (2)0.0161 (18)0.032 (2)
C34A0.065 (3)0.094 (3)0.071 (2)0.035 (2)0.025 (2)0.034 (2)
C35A0.076 (3)0.057 (2)0.082 (2)0.019 (2)0.018 (2)0.0135 (18)
C36A0.0498 (19)0.060 (2)0.072 (2)0.0062 (17)0.0135 (17)0.0116 (18)
P01B0.0449 (5)0.0439 (5)0.0476 (5)0.0034 (4)0.0127 (4)0.0096 (4)
O11B0.0609 (13)0.0474 (13)0.0685 (13)0.0098 (10)0.0228 (11)0.0126 (10)
C11B0.0372 (17)0.0445 (18)0.0479 (18)0.0055 (14)0.0088 (14)0.0061 (14)
C12B0.0451 (18)0.064 (2)0.0498 (19)0.0031 (15)0.0049 (16)0.0161 (16)
C13B0.056 (2)0.105 (3)0.046 (2)0.015 (2)0.0067 (17)0.0190 (19)
C14B0.056 (2)0.112 (3)0.058 (2)0.013 (2)0.0258 (19)0.001 (2)
C15B0.053 (2)0.077 (2)0.070 (2)0.0035 (18)0.0267 (19)0.002 (2)
C16B0.0459 (18)0.057 (2)0.058 (2)0.0016 (16)0.0112 (16)0.0085 (16)
C21B0.0519 (19)0.0485 (19)0.0433 (18)0.0044 (15)0.0092 (15)0.0013 (15)
C22B0.089 (3)0.086 (3)0.072 (3)0.031 (2)0.016 (2)0.021 (2)
C23B0.091 (3)0.102 (3)0.087 (3)0.028 (3)0.028 (3)0.008 (3)
C24B0.089 (3)0.093 (3)0.058 (2)0.016 (3)0.013 (2)0.006 (2)
C25B0.091 (3)0.114 (4)0.068 (3)0.003 (3)0.007 (2)0.040 (2)
C26B0.066 (2)0.085 (3)0.065 (2)0.0027 (19)0.0005 (19)0.031 (2)
C31B0.0440 (18)0.055 (2)0.0437 (17)0.0021 (15)0.0089 (14)0.0153 (15)
C32B0.049 (2)0.062 (2)0.060 (2)0.0091 (17)0.0158 (17)0.0185 (16)
C33B0.048 (2)0.103 (3)0.076 (3)0.005 (2)0.0206 (19)0.039 (2)
C34B0.053 (2)0.089 (3)0.084 (3)0.018 (2)0.001 (2)0.039 (2)
C35B0.071 (3)0.065 (2)0.090 (3)0.015 (2)0.014 (2)0.012 (2)
C36B0.057 (2)0.056 (2)0.080 (2)0.0051 (17)0.0256 (19)0.0073 (18)
Geometric parameters (Å, º) top
C1A—O1A1.436 (4)C6B'—H6B40.9700
C1A—C2A1.499 (4)O1B'—H1B20.8200
C1A—C6A1.507 (5)O2B'—H2B20.8200
C1A—H1A0.9800P01A—O11A1.483 (2)
C2A—O2A1.442 (5)P01A—C21A1.798 (3)
C2A—C3A1.511 (5)P01A—C31A1.800 (3)
C2A—H2A0.9800P01A—C11A1.805 (3)
C3A—C4A1.523 (6)C11A—C12A1.386 (4)
C3A—H3A10.9700C11A—C16A1.391 (4)
C3A—H3A20.9700C12A—C13A1.383 (4)
C4A—C5A1.510 (5)C12A—H12A0.9300
C4A—H4A10.9700C13A—C14A1.367 (5)
C4A—H4A20.9700C13A—H13A0.9300
C5A—C6A1.504 (5)C14A—C15A1.368 (4)
C5A—H5A10.9700C14A—H14A0.9300
C5A—H5A20.9700C15A—C16A1.387 (4)
C6A—H6A10.9700C15A—H15A0.9300
C6A—H6A20.9700C16A—H16A0.9300
O1A—H1A10.8200C21A—C26A1.364 (4)
O2A—H2A10.8200C21A—C22A1.379 (4)
C1A'—O1A'1.438 (6)C22A—C23A1.383 (5)
C1A'—C2A'1.498 (6)C22A—H22A0.9300
C1A'—C6A'1.505 (8)C23A—C24A1.351 (5)
C1A'—H1A'0.9800C23A—H23A0.9300
C2A'—O2A'1.443 (7)C24A—C25A1.348 (6)
C2A'—C3A'1.513 (6)C24A—H24A0.9300
C2A'—H2A'0.9800C25A—C26A1.390 (5)
C3A'—C4A'1.526 (8)C25A—H25A0.9300
C3A'—H3A30.9700C26A—H26A0.9300
C3A'—H3A40.9700C31A—C32A1.385 (4)
C4A'—C5A'1.512 (6)C31A—C36A1.386 (4)
C4A'—H4A30.9700C32A—C33A1.388 (4)
C4A'—H4A40.9700C32A—H32A0.9300
C5A'—C6A'1.499 (6)C33A—C34A1.360 (4)
C5A'—H5A30.9700C33A—H33A0.9300
C5A'—H5A40.9700C34A—C35A1.366 (5)
C6A'—H6A30.9700C34A—H34A0.9300
C6A'—H6A40.9700C35A—C36A1.377 (4)
O1A'—H1A20.8200C35A—H35A0.9300
O2A'—H2A20.8200C36A—H36A0.9300
C1B—O1B1.436 (4)P01B—O11B1.476 (2)
C1B—C2B1.493 (4)P01B—C21B1.794 (3)
C1B—C6B1.500 (5)P01B—C11B1.803 (3)
C1B—H1B0.9800P01B—C31B1.809 (3)
C2B—O2B1.425 (6)C11B—C16B1.384 (4)
C2B—C3B1.508 (5)C11B—C12B1.393 (4)
C2B—H2B0.9800C12B—C13B1.385 (4)
C3B—C4B1.531 (5)C12B—H12B0.9300
C3B—H3B10.9700C13B—C14B1.365 (5)
C3B—H3B20.9700C13B—H13B0.9300
C4B—C5B1.509 (5)C14B—C15B1.366 (5)
C4B—H4B10.9700C14B—H14B0.9300
C4B—H4B20.9700C15B—C16B1.389 (4)
C5B—C6B1.501 (5)C15B—H15B0.9300
C5B—H5B10.9700C16B—H16B0.9300
C5B—H5B20.9700C21B—C26B1.362 (4)
C6B—H6B10.9700C21B—C22B1.388 (4)
C6B—H6B20.9700C22B—C23B1.388 (5)
O1B—H1B10.8200C22B—H22B0.9300
O2B—H2B10.8200C23B—C24B1.352 (5)
C1B'—O1B'1.437 (7)C23B—H23B0.9300
C1B'—C2B'1.497 (6)C24B—C25B1.349 (5)
C1B'—C6B'1.500 (8)C24B—H24B0.9300
C1B'—H1B'0.9800C25B—C26B1.386 (4)
C2B'—O2B'1.426 (9)C25B—H25B0.9300
C2B'—C3B'1.508 (7)C26B—H26B0.9300
C2B'—H2B'0.9800C31B—C36B1.373 (4)
C3B'—C4B'1.530 (8)C31B—C32B1.385 (4)
C3B'—H3B30.9700C32B—C33B1.381 (4)
C3B'—H3B40.9700C32B—H32B0.9300
C4B'—C5B'1.508 (7)C33B—C34B1.365 (4)
C4B'—H4B30.9700C33B—H33B0.9300
C4B'—H4B40.9700C34B—C35B1.367 (5)
C5B'—C6B'1.497 (6)C34B—H34B0.9300
C5B'—H5B30.9700C35B—C36B1.383 (5)
C5B'—H5B40.9700C35B—H35B0.9300
C6B'—H6B30.9700C36B—H36B0.9300
O1A—C1A—C2A107.4 (3)C6B'—C5B'—C4B'111.3 (8)
O1A—C1A—C6A111.8 (4)C6B'—C5B'—H5B3109.4
C2A—C1A—C6A111.8 (4)C4B'—C5B'—H5B3109.4
O1A—C1A—H1A108.6C6B'—C5B'—H5B4109.4
C2A—C1A—H1A108.6C4B'—C5B'—H5B4109.4
C6A—C1A—H1A108.6H5B3—C5B'—H5B4108.0
O2A—C2A—C1A110.4 (4)C5B'—C6B'—C1B'112.1 (9)
O2A—C2A—C3A108.5 (4)C5B'—C6B'—H6B3109.2
C1A—C2A—C3A110.4 (4)C1B'—C6B'—H6B3109.2
O2A—C2A—H2A109.2C5B'—C6B'—H6B4109.2
C1A—C2A—H2A109.2C1B'—C6B'—H6B4109.2
C3A—C2A—H2A109.2H6B3—C6B'—H6B4107.9
C2A—C3A—C4A111.1 (4)C1B'—O1B'—H1B2109.5
C2A—C3A—H3A1109.4C2B'—O2B'—H2B2109.5
C4A—C3A—H3A1109.4O11A—P01A—C21A113.74 (12)
C2A—C3A—H3A2109.4O11A—P01A—C31A111.37 (13)
C4A—C3A—H3A2109.4C21A—P01A—C31A106.76 (14)
H3A1—C3A—H3A2108.0O11A—P01A—C11A111.98 (12)
C5A—C4A—C3A111.3 (4)C21A—P01A—C11A106.00 (13)
C5A—C4A—H4A1109.4C31A—P01A—C11A106.51 (13)
C3A—C4A—H4A1109.4C12A—C11A—C16A119.4 (3)
C5A—C4A—H4A2109.4C12A—C11A—P01A117.3 (2)
C3A—C4A—H4A2109.4C16A—C11A—P01A123.3 (2)
H4A1—C4A—H4A2108.0C13A—C12A—C11A120.3 (3)
C6A—C5A—C4A110.7 (4)C13A—C12A—H12A119.9
C6A—C5A—H5A1109.5C11A—C12A—H12A119.9
C4A—C5A—H5A1109.5C14A—C13A—C12A119.7 (3)
C6A—C5A—H5A2109.5C14A—C13A—H13A120.1
C4A—C5A—H5A2109.5C12A—C13A—H13A120.1
H5A1—C5A—H5A2108.1C13A—C14A—C15A120.8 (3)
C5A—C6A—C1A111.9 (5)C13A—C14A—H14A119.6
C5A—C6A—H6A1109.2C15A—C14A—H14A119.6
C1A—C6A—H6A1109.2C14A—C15A—C16A120.2 (3)
C5A—C6A—H6A2109.2C14A—C15A—H15A119.9
C1A—C6A—H6A2109.2C16A—C15A—H15A119.9
H6A1—C6A—H6A2107.9C15A—C16A—C11A119.5 (3)
O1A'—C1A'—C2A'108.0 (7)C15A—C16A—H16A120.2
O1A'—C1A'—C6A'110.9 (8)C11A—C16A—H16A120.2
C2A'—C1A'—C6A'112.9 (8)C26A—C21A—C22A117.9 (3)
O1A'—C1A'—H1A'108.3C26A—C21A—P01A123.3 (2)
C2A'—C1A'—H1A'108.3C22A—C21A—P01A118.8 (3)
C6A'—C1A'—H1A'108.3C21A—C22A—C23A120.4 (4)
O2A'—C2A'—C1A'110.3 (8)C21A—C22A—H22A119.8
O2A'—C2A'—C3A'107.6 (8)C23A—C22A—H22A119.8
C1A'—C2A'—C3A'111.2 (7)C24A—C23A—C22A120.9 (4)
O2A'—C2A'—H2A'109.3C24A—C23A—H23A119.6
C1A'—C2A'—H2A'109.3C22A—C23A—H23A119.6
C3A'—C2A'—H2A'109.3C25A—C24A—C23A119.4 (4)
C2A'—C3A'—C4A'110.2 (9)C25A—C24A—H24A120.3
C2A'—C3A'—H3A3109.6C23A—C24A—H24A120.3
C4A'—C3A'—H3A3109.6C24A—C25A—C26A120.6 (4)
C2A'—C3A'—H3A4109.6C24A—C25A—H25A119.7
C4A'—C3A'—H3A4109.6C26A—C25A—H25A119.7
H3A3—C3A'—H3A4108.1C21A—C26A—C25A120.8 (3)
C5A'—C4A'—C3A'109.6 (9)C21A—C26A—H26A119.6
C5A'—C4A'—H4A3109.8C25A—C26A—H26A119.6
C3A'—C4A'—H4A3109.8C32A—C31A—C36A118.3 (3)
C5A'—C4A'—H4A4109.8C32A—C31A—P01A118.0 (2)
C3A'—C4A'—H4A4109.8C36A—C31A—P01A123.7 (2)
H4A3—C4A'—H4A4108.2C31A—C32A—C33A120.2 (3)
C6A'—C5A'—C4A'110.9 (8)C31A—C32A—H32A119.9
C6A'—C5A'—H5A3109.5C33A—C32A—H32A119.9
C4A'—C5A'—H5A3109.5C34A—C33A—C32A120.4 (3)
C6A'—C5A'—H5A4109.5C34A—C33A—H33A119.8
C4A'—C5A'—H5A4109.5C32A—C33A—H33A119.8
H5A3—C5A'—H5A4108.1C33A—C34A—C35A120.0 (3)
C5A'—C6A'—C1A'112.7 (9)C33A—C34A—H34A120.0
C5A'—C6A'—H6A3109.0C35A—C34A—H34A120.0
C1A'—C6A'—H6A3109.0C34A—C35A—C36A120.3 (3)
C5A'—C6A'—H6A4109.0C34A—C35A—H35A119.8
C1A'—C6A'—H6A4109.0C36A—C35A—H35A119.8
H6A3—C6A'—H6A4107.8C35A—C36A—C31A120.7 (3)
C1A'—O1A'—H1A2109.5C35A—C36A—H36A119.7
C2A'—O2A'—H2A2109.5C31A—C36A—H36A119.7
O1B—C1B—C2B111.0 (3)O11B—P01B—C21B113.58 (13)
O1B—C1B—C6B109.0 (4)O11B—P01B—C11B111.84 (12)
C2B—C1B—C6B111.4 (4)C21B—P01B—C11B106.06 (13)
O1B—C1B—H1B108.4O11B—P01B—C31B111.84 (13)
C2B—C1B—H1B108.4C21B—P01B—C31B106.33 (14)
C6B—C1B—H1B108.4C11B—P01B—C31B106.71 (13)
O2B—C2B—C1B108.4 (4)C16B—C11B—C12B119.1 (3)
O2B—C2B—C3B112.0 (5)C16B—C11B—P01B123.5 (2)
C1B—C2B—C3B111.3 (4)C12B—C11B—P01B117.3 (2)
O2B—C2B—H2B108.4C13B—C12B—C11B120.2 (3)
C1B—C2B—H2B108.4C13B—C12B—H12B119.9
C3B—C2B—H2B108.4C11B—C12B—H12B119.9
C2B—C3B—C4B110.9 (4)C14B—C13B—C12B120.2 (3)
C2B—C3B—H3B1109.5C14B—C13B—H13B119.9
C4B—C3B—H3B1109.5C12B—C13B—H13B119.9
C2B—C3B—H3B2109.5C13B—C14B—C15B120.2 (3)
C4B—C3B—H3B2109.5C13B—C14B—H14B119.9
H3B1—C3B—H3B2108.0C15B—C14B—H14B119.9
C5B—C4B—C3B110.6 (4)C14B—C15B—C16B120.7 (3)
C5B—C4B—H4B1109.5C14B—C15B—H15B119.6
C3B—C4B—H4B1109.5C16B—C15B—H15B119.6
C5B—C4B—H4B2109.5C11B—C16B—C15B119.6 (3)
C3B—C4B—H4B2109.5C11B—C16B—H16B120.2
H4B1—C4B—H4B2108.1C15B—C16B—H16B120.2
C6B—C5B—C4B111.7 (4)C26B—C21B—C22B117.3 (3)
C6B—C5B—H5B1109.3C26B—C21B—P01B124.3 (3)
C4B—C5B—H5B1109.3C22B—C21B—P01B118.4 (3)
C6B—C5B—H5B2109.3C23B—C22B—C21B120.6 (4)
C4B—C5B—H5B2109.3C23B—C22B—H22B119.7
H5B1—C5B—H5B2107.9C21B—C22B—H22B119.7
C1B—C6B—C5B112.5 (4)C24B—C23B—C22B120.5 (4)
C1B—C6B—H6B1109.1C24B—C23B—H23B119.8
C5B—C6B—H6B1109.1C22B—C23B—H23B119.8
C1B—C6B—H6B2109.1C25B—C24B—C23B119.7 (4)
C5B—C6B—H6B2109.1C25B—C24B—H24B120.2
H6B1—C6B—H6B2107.8C23B—C24B—H24B120.2
O1B'—C1B'—C2B'110.3 (9)C24B—C25B—C26B120.4 (4)
O1B'—C1B'—C6B'108.8 (9)C24B—C25B—H25B119.8
C2B'—C1B'—C6B'112.0 (9)C26B—C25B—H25B119.8
O1B'—C1B'—H1B'108.6C21B—C26B—C25B121.5 (3)
C2B'—C1B'—H1B'108.6C21B—C26B—H26B119.2
C6B'—C1B'—H1B'108.6C25B—C26B—H26B119.2
O2B'—C2B'—C1B'108.0 (10)C36B—C31B—C32B118.2 (3)
O2B'—C2B'—C3B'111.8 (10)C36B—C31B—P01B123.7 (2)
C1B'—C2B'—C3B'111.5 (8)C32B—C31B—P01B118.1 (2)
O2B'—C2B'—H2B'108.5C33B—C32B—C31B120.6 (3)
C1B'—C2B'—H2B'108.5C33B—C32B—H32B119.7
C3B'—C2B'—H2B'108.5C31B—C32B—H32B119.7
C2B'—C3B'—C4B'111.2 (9)C34B—C33B—C32B120.3 (3)
C2B'—C3B'—H3B3109.4C34B—C33B—H33B119.9
C4B'—C3B'—H3B3109.4C32B—C33B—H33B119.9
C2B'—C3B'—H3B4109.4C33B—C34B—C35B119.9 (3)
C4B'—C3B'—H3B4109.4C33B—C34B—H34B120.1
H3B3—C3B'—H3B4108.0C35B—C34B—H34B120.1
C5B'—C4B'—C3B'111.2 (9)C34B—C35B—C36B120.0 (3)
C5B'—C4B'—H4B3109.4C34B—C35B—H35B120.0
C3B'—C4B'—H4B3109.4C36B—C35B—H35B120.0
C5B'—C4B'—H4B4109.4C31B—C36B—C35B121.1 (3)
C3B'—C4B'—H4B4109.4C31B—C36B—H36B119.5
H4B3—C4B'—H4B4108.0C35B—C36B—H36B119.5
O1A—C1A—C2A—O2A61.0 (7)C26A—C21A—C22A—C23A1.0 (5)
C6A—C1A—C2A—O2A175.9 (4)P01A—C21A—C22A—C23A176.2 (3)
O1A—C1A—C2A—C3A178.9 (4)C21A—C22A—C23A—C24A0.2 (6)
C6A—C1A—C2A—C3A55.9 (8)C22A—C23A—C24A—C25A1.7 (7)
O2A—C2A—C3A—C4A177.0 (4)C23A—C24A—C25A—C26A1.9 (7)
C1A—C2A—C3A—C4A55.9 (8)C22A—C21A—C26A—C25A0.8 (5)
C2A—C3A—C4A—C5A55.8 (9)P01A—C21A—C26A—C25A176.3 (3)
C3A—C4A—C5A—C6A54.8 (10)C24A—C25A—C26A—C21A0.7 (6)
C4A—C5A—C6A—C1A54.7 (11)O11A—P01A—C31A—C32A21.0 (3)
O1A—C1A—C6A—C5A176.4 (5)C21A—P01A—C31A—C32A103.7 (2)
C2A—C1A—C6A—C5A55.9 (10)C11A—P01A—C31A—C32A143.3 (2)
O1A'—C1A'—C2A'—O2A'65.6 (14)O11A—P01A—C31A—C36A158.0 (2)
C6A'—C1A'—C2A'—O2A'171.4 (16)C21A—P01A—C31A—C36A77.3 (3)
O1A'—C1A'—C2A'—C3A'175.2 (13)C11A—P01A—C31A—C36A35.6 (3)
C6A'—C1A'—C2A'—C3A'52.1 (18)C36A—C31A—C32A—C33A1.2 (4)
O2A'—C2A'—C3A'—C4A'177.4 (16)P01A—C31A—C32A—C33A177.8 (2)
C1A'—C2A'—C3A'—C4A'56.6 (17)C31A—C32A—C33A—C34A0.4 (5)
C2A'—C3A'—C4A'—C5A'59.6 (19)C32A—C33A—C34A—C35A1.1 (5)
C3A'—C4A'—C5A'—C6A'57.9 (17)C33A—C34A—C35A—C36A1.8 (5)
C4A'—C5A'—C6A'—C1A'54 (2)C34A—C35A—C36A—C31A1.0 (5)
O1A'—C1A'—C6A'—C5A'172.3 (17)C32A—C31A—C36A—C35A0.5 (5)
C2A'—C1A'—C6A'—C5A'51 (2)P01A—C31A—C36A—C35A178.4 (2)
O1B—C1B—C2B—O2B59.0 (8)O11B—P01B—C11B—C16B158.2 (2)
C6B—C1B—C2B—O2B179.3 (5)C21B—P01B—C11B—C16B33.9 (3)
O1B—C1B—C2B—C3B177.4 (3)C31B—P01B—C11B—C16B79.2 (3)
C6B—C1B—C2B—C3B55.7 (8)O11B—P01B—C11B—C12B22.5 (3)
O2B—C2B—C3B—C4B177.8 (5)C21B—P01B—C11B—C12B146.8 (2)
C1B—C2B—C3B—C4B56.3 (8)C31B—P01B—C11B—C12B100.1 (2)
C2B—C3B—C4B—C5B55.2 (9)C16B—C11B—C12B—C13B1.1 (4)
C3B—C4B—C5B—C6B53.8 (9)P01B—C11B—C12B—C13B178.3 (2)
O1B—C1B—C6B—C5B177.4 (4)C11B—C12B—C13B—C14B0.5 (5)
C2B—C1B—C6B—C5B54.5 (9)C12B—C13B—C14B—C15B1.3 (5)
C4B—C5B—C6B—C1B53.9 (10)C13B—C14B—C15B—C16B0.6 (5)
O1B'—C1B'—C2B'—O2B'61 (2)C12B—C11B—C16B—C15B1.8 (4)
C6B'—C1B'—C2B'—O2B'178 (2)P01B—C11B—C16B—C15B177.5 (2)
O1B'—C1B'—C2B'—C3B'175.8 (16)C14B—C15B—C16B—C11B1.0 (5)
C6B'—C1B'—C2B'—C3B'54.5 (19)O11B—P01B—C21B—C26B115.4 (3)
O2B'—C2B'—C3B'—C4B'175 (2)C11B—P01B—C21B—C26B121.3 (3)
C1B'—C2B'—C3B'—C4B'54 (2)C31B—P01B—C21B—C26B8.0 (3)
C2B'—C3B'—C4B'—C5B'54 (2)O11B—P01B—C21B—C22B62.1 (3)
C3B'—C4B'—C5B'—C6B'54 (2)C11B—P01B—C21B—C22B61.1 (3)
C4B'—C5B'—C6B'—C1B'55 (2)C31B—P01B—C21B—C22B174.5 (3)
O1B'—C1B'—C6B'—C5B'177.0 (19)C26B—C21B—C22B—C23B1.5 (6)
C2B'—C1B'—C6B'—C5B'55 (2)P01B—C21B—C22B—C23B176.2 (3)
O11A—P01A—C11A—C12A23.2 (3)C21B—C22B—C23B—C24B0.3 (7)
C21A—P01A—C11A—C12A147.8 (2)C22B—C23B—C24B—C25B0.9 (7)
C31A—P01A—C11A—C12A98.8 (2)C23B—C24B—C25B—C26B0.8 (7)
O11A—P01A—C11A—C16A158.3 (2)C22B—C21B—C26B—C25B1.6 (5)
C21A—P01A—C11A—C16A33.8 (3)P01B—C21B—C26B—C25B176.0 (3)
C31A—P01A—C11A—C16A79.7 (3)C24B—C25B—C26B—C21B0.5 (6)
C16A—C11A—C12A—C13A0.8 (4)O11B—P01B—C31B—C36B156.1 (2)
P01A—C11A—C12A—C13A177.8 (2)C21B—P01B—C31B—C36B79.4 (3)
C11A—C12A—C13A—C14A0.2 (5)C11B—P01B—C31B—C36B33.5 (3)
C12A—C13A—C14A—C15A0.7 (5)O11B—P01B—C31B—C32B22.9 (3)
C13A—C14A—C15A—C16A0.2 (5)C21B—P01B—C31B—C32B101.6 (2)
C14A—C15A—C16A—C11A0.8 (5)C11B—P01B—C31B—C32B145.5 (2)
C12A—C11A—C16A—C15A1.3 (4)C36B—C31B—C32B—C33B1.0 (4)
P01A—C11A—C16A—C15A177.2 (2)P01B—C31B—C32B—C33B178.0 (2)
O11A—P01A—C21A—C26A114.2 (3)C31B—C32B—C33B—C34B1.0 (5)
C31A—P01A—C21A—C26A9.1 (3)C32B—C33B—C34B—C35B0.1 (5)
C11A—P01A—C21A—C26A122.3 (3)C33B—C34B—C35B—C36B0.8 (6)
O11A—P01A—C21A—C22A62.9 (3)C32B—C31B—C36B—C35B0.2 (5)
C31A—P01A—C21A—C22A173.9 (3)P01B—C31B—C36B—C35B178.8 (3)
C11A—P01A—C21A—C22A60.6 (3)C34B—C35B—C36B—C31B0.8 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1A—H1A1···O1Bi0.821.972.789 (5)172
O2A—H2A1···O1Aii0.821.952.734 (5)159
O1B—H1B1···O2Bi0.822.032.790 (8)154
O2B—H2B1···O2Aii0.821.962.771 (7)172
O1A—H1A2···O2Aii0.822.042.80 (2)155
O2A—H2A2···O2Bii0.821.952.74 (3)161
O1B—H1B2···O1Ai0.822.142.79 (3)136
O2B—H2B2···O1Bi0.822.012.62 (5)132
Symmetry codes: (i) x+1, y+1, z; (ii) x+1, y, z.
(toluene294Ktri) 1:1 rac-1,2-cyclohexanediol triphenylphosphine oxide top
Crystal data top
C6H12O2·C18H15OPZ = 4
Mr = 394.43F(000) = 840
Triclinic, P1Dx = 1.231 Mg m3
a = 9.347 (2) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.000 (2) ÅCell parameters from 7828 reflections
c = 21.563 (3) Åθ = 1.0–27.5°
α = 100.25 (1)°µ = 0.15 mm1
β = 102.51 (1)°T = 294 K
γ = 90.10 (1)°Lath, colorless
V = 2128.0 (7) Å30.25 × 0.15 × 0.15 mm
Data collection top
Nonius KappaCCD
diffractometer
7396 independent reflections
Radiation source: fine-focus sealed tube4371 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.049
Detector resolution: 10 pixels mm-1θmax = 25.0°, θmin = 1.9°
1.0° ω scans at fixed χ = 55°h = 1111
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
k = 1313
Tmin = 0.96, Tmax = 0.98l = 2525
14403 measured 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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0518P)2 + 0.0204P]
where P = (Fo2 + 2Fc2)/3
7396 reflections(Δ/σ)max = 0.001
564 parametersΔρmax = 0.17 e Å3
148 restraintsΔρmin = 0.24 e Å3
Crystal data top
C6H12O2·C18H15OPγ = 90.10 (1)°
Mr = 394.43V = 2128.0 (7) Å3
Triclinic, P1Z = 4
a = 9.347 (2) ÅMo Kα radiation
b = 11.000 (2) ŵ = 0.15 mm1
c = 21.563 (3) ÅT = 294 K
α = 100.25 (1)°0.25 × 0.15 × 0.15 mm
β = 102.51 (1)°
Data collection top
Nonius KappaCCD
diffractometer
7396 independent reflections
Absorption correction: multi-scan
DENZO-SMN (Otwinowski & Minor, 1997)
4371 reflections with I > 2σ(I)
Tmin = 0.96, Tmax = 0.98Rint = 0.049
14403 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.049148 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.01Δρmax = 0.17 e Å3
7396 reflectionsΔρmin = 0.24 e Å3
564 parameters
Special details top

Experimental. The crystal-to-detector distance was 46 mm. Each frame was measured for 65 s. The number of scan sets measured was 7; the total number of frames measured was 828.

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.7749 (8)0.0750 (6)0.0371 (4)0.0529 (19)0.718 (8)
H1A0.82560.05670.00140.063*0.718 (8)
C2A0.7462 (8)0.0434 (6)0.0585 (4)0.055 (2)0.718 (8)
H2A0.69020.02630.09240.066*0.718 (8)
C3A0.8897 (10)0.0999 (7)0.0851 (5)0.073 (3)0.718 (8)
H3A10.86910.17420.10060.087*0.718 (8)
H3A20.94210.12300.05090.087*0.718 (8)
C4A0.9841 (10)0.0107 (7)0.1394 (5)0.079 (3)0.718 (8)
H4A11.07680.04740.15400.095*0.718 (8)
H4A20.93590.00600.17550.095*0.718 (8)
C5A1.0125 (8)0.1099 (7)0.1181 (4)0.081 (2)0.718 (8)
H5A11.06890.16760.15460.098*0.718 (8)
H5A21.06960.09460.08520.098*0.718 (8)
C6A0.8705 (10)0.1657 (6)0.0918 (6)0.069 (2)0.718 (8)
H6A10.89110.23980.07610.083*0.718 (8)
H6A20.81830.18910.12610.083*0.718 (8)
O1A0.6379 (7)0.1253 (8)0.0143 (4)0.068 (2)0.718 (8)
H1A10.65050.19870.01330.102*0.718 (8)
O2A0.6630 (9)0.1308 (8)0.0051 (6)0.072 (3)0.718 (8)
H2A10.57530.11870.00160.108*0.718 (8)
C1A'0.7404 (16)0.0806 (14)0.0547 (7)0.0529 (19)0.282 (8)
H1A'0.67820.09150.08630.063*0.282 (8)
C2A'0.7700 (18)0.0539 (13)0.0381 (8)0.055 (2)0.282 (8)
H2A'0.82450.06560.00360.066*0.282 (8)
C3A'0.860 (2)0.0998 (15)0.0964 (12)0.073 (3)0.282 (8)
H3A30.80310.09540.12940.087*0.282 (8)
H3A40.88210.18560.08380.087*0.282 (8)
C4A'1.000 (2)0.0238 (17)0.1237 (12)0.079 (3)0.282 (8)
H4A31.06130.03390.09210.095*0.282 (8)
H4A41.05380.05230.16190.095*0.282 (8)
C5A'0.969 (2)0.1121 (16)0.1411 (8)0.081 (2)0.282 (8)
H5A30.91340.12280.17480.098*0.282 (8)
H5A41.06020.16030.15760.098*0.282 (8)
C6A'0.882 (3)0.1577 (15)0.0831 (14)0.069 (2)0.282 (8)
H6A30.94080.15320.05070.083*0.282 (8)
H6A40.86010.24350.09540.083*0.282 (8)
O1A'0.665 (2)0.120 (2)0.0026 (10)0.068 (2)0.282 (8)
H1A20.57640.11590.00470.102*0.282 (8)
O2A'0.634 (2)0.1256 (19)0.0159 (16)0.072 (3)0.282 (8)
H2A20.63880.18640.03330.108*0.282 (8)
C1B0.3077 (9)0.5854 (5)0.0536 (3)0.0542 (18)0.817 (10)
H1B0.40160.59890.08520.065*0.817 (10)
C2B0.2680 (9)0.4503 (5)0.0395 (3)0.0557 (18)0.817 (10)
H2B0.17610.43630.00660.067*0.817 (10)
C3B0.2428 (12)0.4076 (6)0.0989 (5)0.080 (2)0.817 (10)
H3B10.33340.41790.13170.096*0.817 (10)
H3B20.21330.32050.08840.096*0.817 (10)
C4B0.1226 (13)0.4825 (7)0.1257 (5)0.097 (3)0.817 (10)
H4B10.02980.46690.09440.116*0.817 (10)
H4B20.11070.45650.16510.116*0.817 (10)
C5B0.1645 (10)0.6189 (6)0.1395 (4)0.086 (2)0.817 (10)
H5B10.08460.66550.15260.104*0.817 (10)
H5B20.24990.63560.17500.104*0.817 (10)
C6B0.1979 (14)0.6605 (6)0.0815 (5)0.0701 (18)0.817 (10)
H6B10.10790.65660.04870.084*0.817 (10)
H6B20.23390.74610.09360.084*0.817 (10)
O1B0.3272 (7)0.6273 (6)0.0047 (3)0.0685 (17)0.817 (10)
H1B10.40460.60270.01330.103*0.817 (10)
O2B0.3789 (19)0.3845 (7)0.0133 (7)0.0786 (19)0.817 (10)
H2B10.35520.31060.00360.118*0.817 (10)
C1B'0.264 (3)0.5754 (19)0.0380 (10)0.0542 (18)0.183 (10)
H1B'0.18230.55230.00060.065*0.183 (10)
C2B'0.320 (3)0.460 (2)0.0608 (13)0.0557 (18)0.183 (10)
H2B'0.40740.48310.09560.067*0.183 (10)
C3B'0.208 (4)0.400 (2)0.0880 (18)0.080 (2)0.183 (10)
H3B30.24950.32960.10550.096*0.183 (10)
H3B40.12290.37130.05380.096*0.183 (10)
C4B'0.161 (5)0.493 (3)0.1418 (15)0.097 (3)0.183 (10)
H4B30.08530.45470.15730.116*0.183 (10)
H4B40.24410.51650.17780.116*0.183 (10)
C5B'0.103 (3)0.607 (3)0.1168 (15)0.086 (2)0.183 (10)
H5B30.01270.58540.08440.104*0.183 (10)
H5B40.08090.66700.15190.104*0.183 (10)
C6B'0.212 (5)0.6640 (19)0.088 (2)0.0701 (18)0.183 (10)
H6B30.16780.73190.06840.084*0.183 (10)
H6B40.29560.69770.12180.084*0.183 (10)
O1B'0.380 (3)0.637 (2)0.0175 (12)0.0685 (17)0.183 (10)
H1B20.34530.68980.00280.103*0.183 (10)
O2B'0.363 (8)0.379 (3)0.009 (3)0.0786 (19)0.183 (10)
H2B20.41770.41730.00620.118*0.183 (10)
P01A0.78702 (17)0.16246 (13)0.33594 (6)0.0457 (4)
O11A0.8439 (4)0.2908 (3)0.34055 (14)0.0616 (11)
C11A0.6323 (6)0.1188 (5)0.2684 (2)0.0431 (14)
C12A0.6190 (6)0.1839 (5)0.2186 (2)0.0523 (15)
H12A0.68610.24830.22160.063*
C13A0.5067 (8)0.1541 (6)0.1641 (3)0.0709 (18)
H13A0.49820.19820.13050.085*
C14A0.4100 (8)0.0606 (6)0.1602 (3)0.075 (2)
H14A0.33550.03970.12330.090*
C15A0.4188 (6)0.0043 (5)0.2093 (3)0.0675 (17)
H15A0.35000.06780.20580.081*
C16A0.5305 (6)0.0246 (4)0.2645 (2)0.0510 (14)
H16A0.53680.01880.29820.061*
C21A0.7250 (7)0.1381 (5)0.4059 (2)0.0500 (15)
C22A0.6091 (9)0.2038 (5)0.4230 (3)0.084 (2)
H22A0.56160.25700.39690.101*
C23A0.5633 (9)0.1911 (6)0.4784 (3)0.099 (3)
H23A0.48290.23330.48860.119*
C24A0.6355 (10)0.1169 (6)0.5181 (3)0.079 (2)
H24A0.61030.11400.55730.095*
C25A0.7412 (10)0.0494 (6)0.5007 (3)0.098 (3)
H25A0.78370.00710.52580.118*
C26A0.7906 (7)0.0610 (5)0.4456 (3)0.0712 (19)
H26A0.86920.01560.43570.085*
C31A0.9248 (6)0.0512 (5)0.3245 (2)0.0450 (14)
C32A1.0694 (7)0.0933 (5)0.3423 (2)0.0581 (15)
H32A1.09270.17580.36100.070*
C33A1.1808 (7)0.0132 (6)0.3326 (3)0.0715 (19)
H33A1.27820.04220.34440.086*
C34A1.1460 (9)0.1091 (7)0.3053 (3)0.077 (2)
H34A1.22010.16280.29860.093*
C35A1.0042 (8)0.1517 (5)0.2883 (3)0.0717 (18)
H35A0.98190.23470.27040.086*
C36A0.8916 (7)0.0721 (6)0.2973 (2)0.0625 (16)
H36A0.79450.10180.28510.075*
P01B0.54877 (17)0.66173 (13)0.33446 (6)0.0468 (4)
O11B0.4976 (4)0.7895 (3)0.33984 (14)0.0555 (10)
C11B0.6368 (6)0.6214 (4)0.2679 (2)0.0448 (14)
C12B0.6020 (7)0.6880 (5)0.2171 (2)0.0565 (16)
H12B0.53740.75200.21930.068*
C13B0.6636 (8)0.6584 (6)0.1637 (2)0.0713 (19)
H13B0.64090.70310.13030.086*
C14B0.7585 (7)0.5628 (6)0.1600 (3)0.075 (2)
H14B0.79820.54230.12370.090*
C15B0.7948 (7)0.4979 (5)0.2097 (3)0.0692 (17)
H15B0.85930.43390.20700.083*
C16B0.7352 (6)0.5274 (5)0.2639 (2)0.0557 (15)
H16B0.76140.48400.29770.067*
C21B0.6792 (7)0.6360 (5)0.4051 (2)0.0493 (15)
C22B0.8111 (9)0.7025 (5)0.4223 (3)0.089 (2)
H22B0.83290.75480.39590.107*
C23B0.9122 (9)0.6928 (6)0.4786 (3)0.101 (3)
H23B0.99920.74070.49020.122*
C24B0.8857 (10)0.6148 (7)0.5165 (3)0.092 (2)
H24B0.95540.60640.55330.110*
C25B0.7544 (8)0.5474 (6)0.5005 (3)0.087 (2)
H25B0.73370.49550.52730.104*
C26B0.6532 (7)0.5570 (5)0.4444 (3)0.075 (2)
H26B0.56620.50920.43320.090*
C31B0.3992 (6)0.5501 (5)0.3216 (2)0.0479 (14)
C32B0.2709 (7)0.5885 (5)0.3405 (2)0.0576 (16)
H32B0.26510.67000.36050.069*
C33B0.1523 (7)0.5071 (6)0.3299 (3)0.071 (2)
H33B0.06700.53430.34250.085*
C34B0.1585 (7)0.3875 (6)0.3013 (3)0.0691 (19)
H34B0.07730.33340.29320.083*
C35B0.2859 (8)0.3474 (6)0.2844 (3)0.0768 (19)
H35B0.29270.26470.26660.092*
C36B0.4032 (7)0.4284 (5)0.2934 (2)0.0639 (17)
H36B0.48750.40020.28020.077*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.043 (3)0.051 (2)0.066 (4)0.003 (2)0.014 (3)0.012 (2)
C2A0.047 (3)0.050 (3)0.069 (5)0.002 (2)0.009 (3)0.017 (2)
C3A0.048 (4)0.076 (3)0.097 (5)0.008 (3)0.006 (3)0.038 (3)
C4A0.058 (4)0.112 (4)0.067 (5)0.001 (3)0.001 (3)0.032 (3)
C5A0.055 (4)0.099 (4)0.083 (5)0.014 (3)0.001 (3)0.015 (3)
C6A0.057 (3)0.059 (3)0.081 (4)0.004 (2)0.011 (3)0.007 (3)
O1A0.049 (3)0.055 (2)0.098 (5)0.011 (2)0.006 (3)0.024 (3)
O2A0.050 (4)0.055 (2)0.103 (5)0.002 (2)0.002 (3)0.010 (2)
C1A'0.043 (3)0.051 (2)0.066 (4)0.003 (2)0.014 (3)0.012 (2)
C2A'0.047 (3)