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The diol host, 1,1'-bis-(4-hydroxyphenyl)cyclohexane (DHPC) and a number of xylidine isomers as guests formed a series of inclusion compounds that gave rise to various host:guest ratios controlled by crystallization temperatures. For the host DHPC with a particular xylidine isomer, the number of guests included generally decreases as the crystallization temperature increases. The crystal structures of these host-guest compounds were elucidated using single-crystal X-ray diffraction. Their thermal stabilities were characterized by TG and DSC analysis. The selectivity of enclathration by the host was measured by carrying out a series of competition experiments. The kinetics of guest decomposition were studied using isothermal and non-isothermal methods and reconciled with the crystal structures.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010876810101881X/an0588sup1.cif
Contains datablocks dc26x1, dc26x1.5, dc26x2.5, dc26x3, dc23x0.5, dc23x2, dc34x0.5, dc34x1, dc35x1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101881X/an0588dc23x05sup2.hkl
Contains datablock dc23x05

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101881X/an0588dc23x2sup3.hkl
Contains datablock dc23x2

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101881X/an0588dc26x1sup4.hkl
Contains datablock dc26x1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101881X/an0588dc26x15sup5.hkl
Contains datablock dc26x15

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101881X/an0588dc26x5sup6.hkl
Contains datablock dc26x5

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101881X/an0588dc26x3sup7.hkl
Contains datablock dc26x3

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101881X/an0588dc34x05sup8.hkl
Contains datablock dc34x05

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101881X/an0588dc34x1sup9.hkl
Contains datablock dc34x1

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010876810101881X/an0588dc35x1sup10.hkl
Supplementary material

CCDC references: 184876; 184877; 184878; 184879; 184880; 184881; 184882; 184883; 184884

Computing details top

For all compounds, data collection: COLLECT (2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

(dc26x1) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 2,6-xylidine top
Crystal data top
C18H20O2/C8H11NZ = 2
Mr = 389.52F(000) = 420
Triclinic, P1Dx = 1.162 Mg m3
Dm = N/A Mg m3
Dm measured by not measured
a = 6.234 (1) ÅMelting point: 365.55K for guest release onset temp. and 463.15K for host melting K
b = 10.934 (2) ÅMo Kα radiation, λ = 0.71070 Å
c = 16.974 (2) ŵ = 0.07 mm1
α = 84.98 (1)°T = 293 K
β = 81.29 (2)°Prism, colourless
γ = 77.10 (2)°0.40 × 0.30 × 0.25 mm
V = 1113.1 (3) Å3
Data collection top
Nonius Kappa CCD
diffractometer
2435 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 25.0°, θmin = 1.9°
φ scans and ω scansh = 07
4040 measured reflectionsk = 1212
3895 independent reflectionsl = 1920
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.185 w = 1/[σ2(Fo2) + (0.067P)2 + 0.7169P]
where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max = 0.112
3895 reflectionsΔρmax = 0.78 e Å3
347 parametersΔρmin = 0.17 e Å3
20 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.026 (4)
Special details top

Experimental. Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40 mm; combination of φ and ω scans of 1°, 80 s per °, 2 iterations.

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)
O10.1197 (4)0.36309 (18)0.79798 (12)0.0613 (6)
C10.2289 (4)0.7892 (2)0.58660 (14)0.0361 (5)
O20.1639 (3)1.21323 (19)0.77408 (13)0.0627 (6)
C20.1009 (4)0.8025 (2)0.51394 (15)0.0417 (6)
H210.05350.80160.53310.050*
H220.10560.88340.48610.050*
C30.1913 (4)0.6999 (3)0.45497 (15)0.0473 (6)
H310.16960.61980.48040.057*
H320.10940.71760.40960.057*
C40.4368 (5)0.6910 (3)0.42602 (17)0.0554 (7)
H410.49290.61940.39320.066*
H420.45680.76620.39350.066*
C50.5667 (4)0.6770 (3)0.49590 (17)0.0513 (7)
H510.72100.67730.47620.062*
H520.56090.59690.52470.062*
C60.4741 (4)0.7827 (2)0.55258 (16)0.0430 (6)
H610.48840.86220.52430.052*
H620.56170.77050.59640.052*
C70.2033 (4)0.6718 (2)0.64147 (14)0.0380 (6)
C80.3412 (4)0.6289 (2)0.69972 (16)0.0474 (6)
H80.45300.67080.70400.057*
C90.3186 (5)0.5274 (3)0.75100 (16)0.0505 (7)
H90.41620.50090.78850.061*
C100.1528 (4)0.4643 (2)0.74753 (15)0.0441 (6)
C110.0113 (4)0.5048 (2)0.69115 (16)0.0489 (7)
H110.10260.46370.68830.059*
C120.0376 (4)0.6059 (2)0.63904 (16)0.0448 (6)
H120.05860.63100.60100.054*
C130.1328 (4)0.9043 (2)0.63672 (14)0.0381 (6)
C140.2515 (4)0.9919 (2)0.64947 (16)0.0472 (6)
H140.39930.98160.62670.057*
C150.1573 (4)1.0947 (2)0.69510 (17)0.0507 (7)
H150.24221.15130.70310.061*
C160.0618 (4)1.1124 (2)0.72846 (15)0.0457 (6)
C170.1846 (4)1.0279 (3)0.71625 (17)0.0538 (7)
H170.33331.03960.73810.065*
C180.0880 (4)0.9263 (3)0.67190 (17)0.0497 (7)
H180.17360.86940.66500.060*
N1GA0.4320 (10)0.2979 (6)0.9128 (4)0.0677 (16)0.500 (4)
C1GA0.3272 (17)0.2419 (8)0.9783 (4)0.048 (3)0.535 (17)
C2GA0.2248 (13)0.3084 (6)1.0490 (4)0.083 (2)0.500 (4)
C3GA0.1183 (19)0.2511 (10)1.1075 (5)0.094 (8)0.500 (4)
H3GA0.05570.29711.15200.113*0.500 (4)
C4GA0.0893 (17)0.1324 (10)1.1105 (5)0.103 (3)0.500 (4)
H4GA0.00720.09891.15410.124*0.500 (4)
C5GA0.1870 (15)0.0633 (8)1.0459 (5)0.095 (3)0.500 (4)
H5GA0.17480.01991.04560.114*0.500 (4)
C6GA0.3042 (12)0.1169 (6)0.9808 (4)0.0693 (19)0.500 (4)
C7GA0.242 (2)0.4412 (12)1.0505 (9)0.166 (6)0.500 (4)
H7A10.12960.48241.09040.249*0.500 (4)
H7A20.22160.48310.99920.249*0.500 (4)
H7A30.38600.44421.06280.249*0.500 (4)
C8GA0.4103 (16)0.0416 (7)0.9089 (5)0.100 (3)0.500 (4)
H8A10.34960.03210.91070.150*0.500 (4)
H8A20.56780.01710.90960.150*0.500 (4)
H8A30.38070.09200.86100.150*0.500 (4)
N1GB0.4038 (9)0.2269 (6)0.8889 (3)0.0577 (14)0.500 (4)
C1GB0.3644 (10)0.2537 (6)0.9722 (5)0.084 (7)0.500 (4)
C2GB0.1664 (11)0.2251 (5)1.0144 (3)0.080 (2)0.500 (4)
C3GB0.110 (2)0.2517 (7)1.1032 (3)0.136 (13)0.500 (4)
H3GB0.01700.23661.13510.163*0.500 (4)
C4GB0.269 (2)0.3005 (12)1.1307 (6)0.131 (5)0.500 (4)
H4GB0.24770.31711.18450.157*0.500 (4)
C5GB0.4511 (18)0.3256 (9)1.0866 (5)0.105 (3)0.500 (4)
H5GB0.54690.35961.11080.126*0.500 (4)
C6GB0.5043 (13)0.3035 (6)1.0061 (4)0.0718 (19)0.500 (4)
C7GB0.0047 (11)0.1727 (6)0.9762 (5)0.123 (4)0.500 (4)
H7B10.02210.21950.92680.185*0.500 (4)
H7B20.13260.17941.01150.185*0.500 (4)
H7B30.06630.08610.96600.185*0.500 (4)
C8GB0.7084 (15)0.3327 (8)0.9581 (6)0.097 (3)0.500 (4)
H8B10.80780.25600.94160.146*0.500 (4)
H8B20.77990.37580.98970.146*0.500 (4)
H8B30.66940.38510.91180.146*0.500 (4)
H10.24920.33840.82550.125 (17)*
H20.05221.26060.78050.17 (2)*
H1A20.53610.25850.87020.14 (4)*0.500 (4)
H1A10.46780.37610.92150.10 (3)*0.500 (4)
H1B10.39360.15130.86820.12 (3)*0.500 (4)
H1B20.56250.22000.88130.031 (13)*0.500 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0802 (15)0.0503 (11)0.0568 (12)0.0255 (10)0.0079 (11)0.0054 (9)
C10.0306 (11)0.0368 (12)0.0413 (13)0.0087 (9)0.0037 (10)0.0011 (10)
O20.0640 (13)0.0545 (12)0.0676 (13)0.0107 (10)0.0077 (10)0.0250 (10)
C20.0384 (13)0.0421 (13)0.0438 (14)0.0092 (10)0.0047 (10)0.0024 (11)
C30.0492 (15)0.0513 (15)0.0422 (14)0.0101 (12)0.0071 (11)0.0069 (12)
C40.0545 (16)0.0591 (17)0.0490 (16)0.0103 (13)0.0049 (13)0.0095 (13)
C50.0357 (13)0.0516 (16)0.0647 (18)0.0082 (11)0.0026 (12)0.0122 (13)
C60.0337 (12)0.0434 (14)0.0528 (15)0.0114 (10)0.0040 (11)0.0029 (11)
C70.0335 (12)0.0371 (13)0.0438 (13)0.0089 (10)0.0028 (10)0.0055 (10)
C80.0471 (14)0.0501 (15)0.0506 (15)0.0199 (12)0.0122 (12)0.0006 (12)
C90.0561 (16)0.0529 (16)0.0456 (15)0.0151 (13)0.0154 (12)0.0045 (12)
C100.0570 (16)0.0345 (12)0.0394 (13)0.0126 (11)0.0019 (11)0.0014 (10)
C110.0518 (15)0.0504 (15)0.0518 (15)0.0258 (12)0.0075 (12)0.0027 (12)
C120.0440 (14)0.0482 (15)0.0459 (14)0.0144 (11)0.0116 (11)0.0016 (12)
C130.0376 (12)0.0361 (12)0.0409 (13)0.0090 (10)0.0045 (10)0.0020 (10)
C140.0407 (13)0.0448 (14)0.0571 (16)0.0152 (11)0.0021 (12)0.0078 (12)
C150.0504 (15)0.0432 (14)0.0621 (17)0.0185 (12)0.0012 (13)0.0123 (13)
C160.0524 (15)0.0397 (14)0.0423 (14)0.0063 (11)0.0002 (12)0.0077 (11)
C170.0382 (14)0.0639 (18)0.0608 (17)0.0156 (12)0.0043 (12)0.0181 (14)
C180.0419 (14)0.0525 (15)0.0576 (16)0.0173 (12)0.0012 (12)0.0150 (13)
N1GA0.069 (4)0.071 (4)0.063 (4)0.026 (3)0.004 (3)0.001 (3)
C1GA0.046 (4)0.048 (5)0.045 (5)0.001 (4)0.002 (4)0.005 (4)
C2GA0.078 (5)0.086 (6)0.084 (6)0.011 (4)0.005 (4)0.024 (5)
C3GA0.068 (9)0.15 (2)0.062 (9)0.018 (10)0.012 (7)0.033 (11)
C4GA0.124 (8)0.129 (8)0.054 (5)0.034 (7)0.007 (5)0.014 (5)
C5GA0.124 (7)0.070 (5)0.086 (6)0.014 (5)0.026 (5)0.022 (4)
C6GA0.081 (5)0.065 (4)0.051 (4)0.003 (3)0.010 (3)0.012 (3)
C7GA0.175 (12)0.140 (10)0.185 (12)0.071 (9)0.080 (10)0.098 (10)
C8GA0.129 (7)0.066 (5)0.092 (6)0.002 (5)0.001 (5)0.011 (4)
N1GB0.059 (3)0.058 (3)0.055 (3)0.011 (3)0.011 (2)0.002 (3)
C1GB0.082 (10)0.081 (10)0.085 (11)0.000 (7)0.025 (7)0.002 (8)
C2GB0.078 (5)0.088 (6)0.059 (4)0.000 (4)0.000 (4)0.022 (4)
C3GB0.13 (2)0.104 (17)0.126 (18)0.021 (13)0.020 (13)0.047 (12)
C4GB0.140 (10)0.146 (10)0.069 (6)0.023 (8)0.028 (7)0.010 (6)
C5GB0.138 (8)0.098 (6)0.071 (5)0.011 (6)0.031 (6)0.034 (5)
C6GB0.079 (5)0.065 (4)0.069 (4)0.004 (4)0.014 (4)0.014 (3)
C7GB0.098 (7)0.157 (10)0.118 (8)0.057 (7)0.011 (6)0.040 (7)
C8GB0.107 (7)0.087 (6)0.105 (6)0.026 (5)0.022 (5)0.020 (5)
Geometric parameters (Å, º) top
O1—C101.373 (3)N1GA—H1A20.9581
O1—H10.9676N1GA—H1A10.9589
C1—C131.538 (3)N1GA—H1B21.1457
C1—C61.539 (3)C1GA—C6GA1.403 (12)
C1—C71.542 (3)C1GA—C2GA1.4451
C1—C21.547 (3)C2GA—C3GA1.3032
O2—C161.381 (3)C2GA—C7GA1.483 (13)
O2—H20.9794C3GA—C4GA1.345 (13)
C2—C31.523 (3)C3GA—H3GA0.9300
C2—H210.9700C4GA—C5GA1.372 (11)
C2—H220.9700C4GA—H4GA0.9300
C3—C41.519 (4)C5GA—C6GA1.390 (10)
C3—H310.9700C5GA—H5GA0.9300
C3—H320.9700C6GA—C8GA1.513 (10)
C4—C51.513 (4)C7GA—H7A10.9600
C4—H410.9700C7GA—H7A20.9600
C4—H420.9700C7GA—H7A30.9600
C5—C61.525 (4)C8GA—H8A10.9600
C5—H510.9700C8GA—H8A20.9600
C5—H520.9700C8GA—H8A30.9600
C6—H610.9700C8GA—H1B11.3225
C6—H620.9700N1GB—C1GB1.444 (10)
C7—C81.390 (4)N1GB—H1A20.9637
C7—C121.392 (3)N1GB—H1B10.9448
C8—C91.368 (4)N1GB—H1B20.9648
C8—H80.9300C1GB—C6GB1.344 (10)
C9—C101.376 (4)C1GB—C2GB1.4139
C9—H90.9300C2GB—C7GB1.5118
C10—C111.378 (4)C2GB—C3GB1.5317
C11—C121.377 (4)C3GB—C4GB1.381 (16)
C11—H110.9300C3GB—H3GB0.9300
C12—H120.9300C4GB—C5GB1.329 (13)
C13—C141.383 (3)C4GB—H4GB0.9300
C13—C181.392 (3)C5GB—C6GB1.386 (10)
C14—C151.388 (4)C5GB—H5GB0.9300
C14—H140.9300C6GB—C8GB1.485 (11)
C15—C161.375 (4)C7GB—H7B10.9600
C15—H150.9300C7GB—H7B20.9600
C16—C171.372 (4)C7GB—H7B30.9600
C17—C181.369 (4)C8GB—H8B10.9600
C17—H170.9300C8GB—H8B20.9600
C18—H180.9300C8GB—H8B30.9600
N1GA—C1GA1.370 (10)
C10—O1—H1106.1C16—C15—H15120.1
C13—C1—C6111.72 (19)C14—C15—H15120.1
C13—C1—C7107.17 (19)C17—C16—C15119.4 (2)
C6—C1—C7110.68 (19)C17—C16—O2118.4 (2)
C13—C1—C2108.33 (18)C15—C16—O2122.2 (2)
C6—C1—C2106.38 (19)C18—C17—C16119.9 (2)
C7—C1—C2112.62 (19)C18—C17—H17120.0
C16—O2—H2108.4C16—C17—H17120.0
C3—C2—C1114.1 (2)C17—C18—C13122.9 (2)
C3—C2—H21108.7C17—C18—H18118.6
C1—C2—H21108.7C13—C18—H18118.6
C3—C2—H22108.7N1GA—C1GA—C6GA122.5 (6)
C1—C2—H22108.7N1GA—C1GA—C2GA122.6 (7)
H21—C2—H22107.6C6GA—C1GA—C2GA114.8 (6)
C4—C3—C2111.6 (2)C3GA—C2GA—C1GA119.3
C4—C3—H31109.3C3GA—C2GA—C7GA122.9 (7)
C2—C3—H31109.3C1GA—C2GA—C7GA117.8 (7)
C4—C3—H32109.3C2GA—C3GA—C4GA126.9 (7)
C2—C3—H32109.3C2GA—C3GA—H3GA116.5
H31—C3—H32108.0C4GA—C3GA—H3GA116.5
C5—C4—C3110.7 (2)C3GA—C4GA—C5GA116.5 (8)
C5—C4—H41109.5C3GA—C4GA—H4GA121.7
C3—C4—H41109.5C5GA—C4GA—H4GA121.7
C5—C4—H42109.5C4GA—C5GA—C6GA120.4 (8)
C3—C4—H42109.5C4GA—C5GA—H5GA119.8
H41—C4—H42108.1C6GA—C5GA—H5GA119.8
C4—C5—C6111.5 (2)C5GA—C6GA—C1GA121.9 (7)
C4—C5—H51109.3C5GA—C6GA—C8GA120.7 (7)
C6—C5—H51109.3C1GA—C6GA—C8GA117.4 (6)
C4—C5—H52109.3C1GB—N1GB—H1A2102.1
C6—C5—H52109.3C1GB—N1GB—H1B1125.6
H51—C5—H52108.0C1GB—N1GB—H1B297.2
C5—C6—C1112.7 (2)H1B1—N1GB—H1B2101.2
C5—C6—H61109.0C6GB—C1GB—C2GB123.2 (6)
C1—C6—H61109.0C6GB—C1GB—N1GB122.2 (6)
C5—C6—H62109.0C2GB—C1GB—N1GB114.6 (4)
C1—C6—H62109.0C1GB—C2GB—C7GB123.5
H61—C6—H62107.8C1GB—C2GB—C3GB118.1
C8—C7—C12115.8 (2)C7GB—C2GB—C3GB118.4
C8—C7—C1121.0 (2)C4GB—C3GB—C2GB112.8 (7)
C12—C7—C1123.1 (2)C4GB—C3GB—H3GB123.6
C9—C8—C7122.5 (2)C2GB—C3GB—H3GB123.6
C9—C8—H8118.7C5GB—C4GB—C3GB125.2 (10)
C7—C8—H8118.7C5GB—C4GB—H4GB117.4
C8—C9—C10120.5 (3)C3GB—C4GB—H4GB117.4
C8—C9—H9119.8C4GB—C5GB—C6GB123.0 (10)
C10—C9—H9119.8C4GB—C5GB—H5GB118.5
O1—C10—C9123.3 (2)C6GB—C5GB—H5GB118.5
O1—C10—C11118.0 (2)C1GB—C6GB—C5GB117.6 (8)
C9—C10—C11118.7 (2)C1GB—C6GB—C8GB120.5 (7)
C12—C11—C10120.3 (2)C5GB—C6GB—C8GB121.9 (8)
C12—C11—H11119.9C2GB—C7GB—H7B1109.5
C10—C11—H11119.9C2GB—C7GB—H7B2109.5
C11—C12—C7122.2 (2)H7B1—C7GB—H7B2109.5
C11—C12—H12118.9C2GB—C7GB—H7B3109.5
C7—C12—H12118.9H7B1—C7GB—H7B3109.5
C14—C13—C18115.8 (2)H7B2—C7GB—H7B3109.5
C14—C13—C1124.3 (2)C6GB—C8GB—H8B1109.5
C18—C13—C1119.9 (2)C6GB—C8GB—H8B2109.5
C13—C14—C15122.2 (2)H8B1—C8GB—H8B2109.5
C13—C14—H14118.9C6GB—C8GB—H8B3109.5
C15—C14—H14118.9H8B1—C8GB—H8B3109.5
C16—C15—C14119.8 (2)H8B2—C8GB—H8B3109.5
C13—C1—C2—C3175.2 (2)C14—C15—C16—C170.1 (4)
C6—C1—C2—C354.9 (3)C14—C15—C16—O2179.8 (3)
C7—C1—C2—C366.5 (3)C15—C16—C17—C180.7 (4)
C1—C2—C3—C455.2 (3)O2—C16—C17—C18179.4 (3)
C2—C3—C4—C553.1 (3)C16—C17—C18—C130.9 (5)
C3—C4—C5—C655.1 (3)C14—C13—C18—C170.2 (4)
C4—C5—C6—C158.9 (3)C1—C13—C18—C17179.0 (3)
C13—C1—C6—C5174.2 (2)N1GA—C1GA—C2GA—C3GA176.6 (10)
C7—C1—C6—C566.4 (3)C6GA—C1GA—C2GA—C3GA1.2 (14)
C2—C1—C6—C556.2 (3)N1GA—C1GA—C2GA—C7GA2.0 (15)
C13—C1—C7—C874.7 (3)C6GA—C1GA—C2GA—C7GA179.8 (10)
C6—C1—C7—C847.3 (3)C1GA—C2GA—C3GA—C4GA0.4 (19)
C2—C1—C7—C8166.2 (2)C7GA—C2GA—C3GA—C4GA178.2 (13)
C13—C1—C7—C12102.1 (3)C2GA—C3GA—C4GA—C5GA1.8 (19)
C6—C1—C7—C12135.8 (2)C3GA—C4GA—C5GA—C6GA1.6 (15)
C2—C1—C7—C1216.9 (3)C4GA—C5GA—C6GA—C1GA0.0 (13)
C12—C7—C8—C90.9 (4)C4GA—C5GA—C6GA—C8GA179.3 (9)
C1—C7—C8—C9177.9 (2)N1GA—C1GA—C6GA—C5GA176.4 (8)
C7—C8—C9—C101.2 (4)C2GA—C1GA—C6GA—C5GA1.4 (12)
C8—C9—C10—O1179.1 (2)N1GA—C1GA—C6GA—C8GA2.9 (13)
C8—C9—C10—C110.4 (4)C2GA—C1GA—C6GA—C8GA179.3 (8)
O1—C10—C11—C12179.9 (2)C6GB—C1GB—C2GB—C7GB178.1 (5)
C9—C10—C11—C120.5 (4)N1GB—C1GB—C2GB—C7GB1.0 (4)
C10—C11—C12—C70.8 (4)C6GB—C1GB—C2GB—C3GB0.4 (5)
C8—C7—C12—C110.1 (4)N1GB—C1GB—C2GB—C3GB179.5 (4)
C1—C7—C12—C11176.9 (2)C1GB—C2GB—C3GB—C4GB0.7 (7)
C6—C1—C13—C140.3 (3)C7GB—C2GB—C3GB—C4GB179.3 (7)
C7—C1—C13—C14121.7 (3)C2GB—C3GB—C4GB—C5GB1.4 (14)
C2—C1—C13—C14116.6 (3)C3GB—C4GB—C5GB—C6GB1.0 (17)
C6—C1—C13—C18179.5 (2)C2GB—C1GB—C6GB—C5GB1.0 (9)
C7—C1—C13—C1859.1 (3)N1GB—C1GB—C6GB—C5GB180.0 (7)
C2—C1—C13—C1862.7 (3)C2GB—C1GB—C6GB—C8GB179.3 (5)
C18—C13—C14—C150.6 (4)N1GB—C1GB—C6GB—C8GB0.3 (10)
C1—C13—C14—C15179.9 (2)C4GB—C5GB—C6GB—C1GB0.3 (13)
C13—C14—C15—C160.8 (4)C4GB—C5GB—C6GB—C8GB179.9 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1GB0.971.772.642 (6)148
O1—H1···N1GA0.971.972.896 (7)160
O2—H2···O1i0.981.782.757 (3)172
N1GA—H1A2···O2ii0.962.283.209 (7)162
N1GB—H1B2···O2ii0.962.293.060 (6)136
Symmetry codes: (i) x, y+1, z; (ii) x+1, y1, z.
(dc26x1.5) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 2,6-xylidine top
Crystal data top
C18H20O2/1.5(C8H11N)Z = 2
Mr = 450.11F(000) = 486
Triclinic, P1Dx = 1.191 Mg m3
Dm = N/A Mg m3
Dm measured by not measured
a = 7.8594 (3) ÅMelting point: 363.65K for guest release onset temp. and 463.15K for host melting K
b = 10.015 (1) ÅMo Kα radiation, λ = 0.71069 Å
c = 17.169 (1) ŵ = 0.07 mm1
α = 78.909 (2)°T = 173 K
β = 85.161 (1)°Prism, colourless
γ = 71.238 (1)°0.50 × 0.35 × 0.15 mm
V = 1255.33 (15) Å3
Data collection top
Nonius Kappa CCD
diffractometer
2742 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 25.6°, θmin = 2.7°
φ scans and ω scansh = 69
6193 measured reflectionsk = 1211
4593 independent reflectionsl = 2020
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0734P)2 + 0.0396P]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max < 0.001
4593 reflectionsΔρmax = 0.42 e Å3
344 parametersΔρmin = 0.18 e Å3
6 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.014 (3)
Special details top

Experimental. Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40 mm; combination of φ and ω scans of 1°, 60 s per °, 2 iterations.

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)
O10.9230 (2)0.59543 (15)0.20898 (9)0.0367 (4)
C70.5408 (3)0.7382 (2)0.38512 (12)0.0254 (5)
O20.7771 (3)0.63742 (18)0.74928 (10)0.0546 (6)
C80.6336 (3)0.8265 (2)0.34196 (13)0.0288 (5)
H80.61060.91970.35370.035*
N1GA1.0563 (3)0.7893 (2)0.10180 (13)0.0378 (5)
C10.4117 (3)0.7841 (2)0.45450 (12)0.0260 (5)
C140.4262 (3)0.7742 (2)0.60361 (13)0.0318 (6)
H140.30060.82290.60290.038*
C130.5163 (3)0.7407 (2)0.53245 (13)0.0259 (5)
C100.7946 (3)0.6476 (2)0.26519 (12)0.0266 (5)
C1GA1.0165 (3)0.9332 (2)0.11471 (13)0.0317 (6)
C110.7033 (3)0.5583 (2)0.30602 (13)0.0311 (6)
H110.72630.46540.29390.037*
C30.1936 (3)0.9999 (2)0.36880 (14)0.0346 (6)
H310.13241.10420.36410.042*
H320.26620.98290.31960.042*
C90.7585 (3)0.7832 (2)0.28235 (13)0.0294 (5)
H90.81870.84650.25360.035*
C2GA1.1429 (3)0.9729 (2)0.14917 (13)0.0329 (6)
C180.6987 (3)0.6692 (2)0.53724 (13)0.0306 (6)
H180.76490.64470.49030.037*
C120.5779 (3)0.6036 (2)0.36479 (13)0.0283 (5)
H120.51530.54090.39210.034*
C20.3177 (3)0.9483 (2)0.43995 (13)0.0307 (6)
H210.24660.97530.48810.037*
H220.41050.99740.43090.037*
C170.7887 (3)0.6318 (2)0.60860 (14)0.0354 (6)
H170.91400.58180.61000.042*
C60.2603 (3)0.7130 (2)0.46456 (13)0.0304 (6)
H610.31550.60770.47260.036*
H620.18690.73710.51270.036*
C160.6954 (4)0.6675 (2)0.67722 (14)0.0379 (6)
C150.5134 (3)0.7389 (2)0.67462 (14)0.0365 (6)
H150.44820.76380.72170.044*
C50.1376 (3)0.7607 (2)0.39329 (14)0.0345 (6)
H510.20810.72950.34580.041*
H520.04160.71490.40370.041*
C6GA0.8461 (3)1.0303 (3)0.09581 (14)0.0396 (6)
C40.0534 (3)0.9226 (2)0.37746 (15)0.0393 (6)
H410.03110.95190.42170.047*
H420.01630.95140.32820.047*
C7GA1.3255 (3)0.8678 (3)0.16988 (15)0.0449 (7)
H7A11.31200.78600.20870.067*
H7A21.39660.91460.19260.067*
H7A31.38680.83440.12180.067*
C3GA1.0982 (4)1.1127 (3)0.16304 (14)0.0463 (7)
H3GA1.18391.14160.18580.056*
C5GA0.8068 (4)1.1687 (3)0.11109 (16)0.0560 (8)
H5GA0.69201.23620.09840.067*
C8GA0.7094 (4)0.9854 (3)0.06041 (17)0.0626 (9)
H8A10.59821.06610.05170.094*
H8A20.68450.90530.09680.094*
H8A30.75620.95550.00960.094*
C4GA0.9314 (5)1.2096 (3)0.14425 (17)0.0593 (9)
H4GA0.90241.30460.15420.071*
H10.969 (4)0.667 (2)0.1772 (14)0.080 (10)*
H20.896 (3)0.564 (2)0.7531 (17)0.092 (11)*
H1A11.181 (3)0.738 (3)0.1010 (17)0.072 (10)*
H1A21.005 (4)0.784 (3)0.0557 (15)0.077 (10)*
N1GB1.4477 (3)0.5150 (2)0.12078 (13)0.0429 (6)0.50
C6GB1.6201 (3)0.5521 (2)0.00147 (14)0.0336 (6)0.50
C1GB1.5132 (7)0.4911 (4)0.0374 (3)0.0308 (11)0.50
C3GB1.3440 (7)0.4510 (5)0.0852 (3)0.0400 (13)0.50
C5GB1.5824 (7)0.5539 (5)0.0834 (3)0.0415 (13)0.50
C7GB1.7399 (8)0.6205 (5)0.0355 (3)0.0524 (15)0.50
C8GB1.7650 (7)0.6009 (5)0.0434 (4)0.0514 (14)0.50
C4GB1.4477 (3)0.5150 (2)0.12078 (13)0.0429 (6)0.50
C2GB1.6201 (3)0.5521 (2)0.00147 (14)0.0336 (6)0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0377 (10)0.0366 (9)0.0325 (10)0.0102 (8)0.0081 (8)0.0042 (7)
C70.0258 (13)0.0258 (11)0.0253 (13)0.0098 (10)0.0033 (10)0.0021 (9)
O20.0690 (14)0.0461 (11)0.0411 (11)0.0012 (10)0.0237 (10)0.0132 (8)
C80.0302 (14)0.0276 (11)0.0329 (14)0.0146 (10)0.0019 (11)0.0053 (10)
N1GA0.0437 (15)0.0398 (12)0.0336 (13)0.0200 (11)0.0028 (11)0.0048 (9)
C10.0263 (13)0.0256 (11)0.0269 (13)0.0096 (10)0.0003 (10)0.0043 (9)
C140.0353 (14)0.0256 (12)0.0329 (14)0.0079 (10)0.0007 (11)0.0041 (10)
C130.0296 (14)0.0215 (11)0.0295 (13)0.0116 (10)0.0007 (10)0.0051 (9)
C100.0238 (13)0.0304 (12)0.0243 (13)0.0077 (10)0.0007 (10)0.0029 (10)
C1GA0.0358 (15)0.0340 (13)0.0230 (13)0.0125 (11)0.0060 (11)0.0002 (10)
C110.0358 (14)0.0267 (11)0.0314 (14)0.0108 (10)0.0006 (11)0.0055 (10)
C30.0340 (14)0.0297 (12)0.0370 (15)0.0057 (11)0.0029 (11)0.0052 (10)
C90.0279 (13)0.0310 (12)0.0313 (14)0.0147 (10)0.0010 (11)0.0008 (10)
C2GA0.0349 (15)0.0372 (13)0.0259 (13)0.0127 (11)0.0035 (11)0.0034 (10)
C180.0330 (15)0.0273 (11)0.0327 (14)0.0107 (10)0.0004 (11)0.0063 (10)
C120.0300 (13)0.0268 (12)0.0300 (13)0.0141 (10)0.0011 (11)0.0014 (9)
C20.0335 (14)0.0280 (12)0.0311 (14)0.0101 (10)0.0000 (11)0.0060 (9)
C170.0360 (15)0.0287 (12)0.0422 (16)0.0085 (10)0.0092 (12)0.0073 (11)
C60.0297 (14)0.0303 (12)0.0320 (14)0.0122 (10)0.0042 (11)0.0049 (10)
C160.0564 (18)0.0265 (12)0.0303 (15)0.0087 (12)0.0130 (13)0.0061 (10)
C150.0496 (17)0.0267 (12)0.0298 (14)0.0061 (11)0.0023 (12)0.0063 (10)
C50.0266 (13)0.0389 (13)0.0402 (15)0.0141 (10)0.0003 (11)0.0060 (10)
C6GA0.0320 (15)0.0512 (16)0.0298 (15)0.0115 (12)0.0009 (11)0.0034 (11)
C40.0329 (15)0.0416 (14)0.0396 (16)0.0064 (11)0.0040 (12)0.0056 (11)
C7GA0.0351 (16)0.0553 (16)0.0453 (17)0.0125 (13)0.0022 (12)0.0136 (12)
C3GA0.0635 (19)0.0404 (15)0.0360 (16)0.0181 (14)0.0027 (13)0.0053 (11)
C5GA0.0523 (19)0.0465 (17)0.0438 (18)0.0104 (14)0.0010 (15)0.0082 (13)
C8GA0.0433 (18)0.086 (2)0.0500 (19)0.0215 (16)0.0085 (15)0.0130 (15)
C4GA0.080 (2)0.0351 (15)0.0510 (19)0.0036 (16)0.0029 (17)0.0046 (13)
N1GB0.0477 (16)0.0431 (13)0.0350 (14)0.0063 (12)0.0005 (12)0.0140 (11)
C6GB0.0355 (15)0.0258 (12)0.0348 (15)0.0016 (11)0.0039 (12)0.0064 (10)
C1GB0.037 (3)0.024 (2)0.027 (3)0.006 (2)0.003 (2)0.000 (2)
C3GB0.050 (3)0.028 (2)0.038 (3)0.008 (2)0.002 (3)0.003 (2)
C5GB0.043 (3)0.026 (2)0.050 (3)0.002 (2)0.009 (3)0.003 (2)
C7GB0.056 (4)0.041 (3)0.066 (4)0.011 (3)0.024 (3)0.018 (3)
C8GB0.044 (4)0.051 (3)0.064 (4)0.022 (3)0.004 (3)0.011 (3)
C4GB0.0477 (16)0.0431 (13)0.0350 (14)0.0063 (12)0.0005 (12)0.0140 (11)
C2GB0.0355 (15)0.0258 (12)0.0348 (15)0.0016 (11)0.0039 (12)0.0064 (10)
Geometric parameters (Å, º) top
O1—C101.383 (2)C15—H150.9500
O1—H10.963 (14)C5—C41.520 (3)
C7—C81.391 (3)C5—H510.9900
C7—C121.391 (3)C5—H520.9900
C7—C11.538 (3)C6GA—C5GA1.392 (4)
O2—C161.378 (3)C6GA—C8GA1.501 (4)
O2—H20.985 (14)C4—H410.9900
C8—C91.388 (3)C4—H420.9900
C8—H80.9500C7GA—H7A10.9800
N1GA—C1GA1.430 (3)C7GA—H7A20.9800
N1GA—H1A10.95 (2)C7GA—H7A30.9800
N1GA—H1A20.93 (2)C3GA—C4GA1.378 (4)
C1—C131.545 (3)C3GA—H3GA0.9500
C1—C21.550 (3)C5GA—C4GA1.376 (4)
C1—C61.554 (3)C5GA—H5GA0.9500
C14—C151.378 (3)C8GA—H8A10.9800
C14—C131.402 (3)C8GA—H8A20.9800
C14—H140.9500C8GA—H8A30.9800
C13—C181.383 (3)C4GA—H4GA0.9500
C10—C111.376 (3)N1GB—C5GB1.318 (6)
C10—C91.380 (3)N1GB—C3GB1.421 (6)
C1GA—C2GA1.393 (3)N1GB—C1GBi1.448 (5)
C1GA—C6GA1.400 (3)C6GB—C1GBi1.339 (5)
C11—C121.384 (3)C6GB—C1GB1.422 (6)
C11—H110.9500C6GB—C3GBi1.446 (5)
C3—C41.521 (3)C6GB—C8GB1.462 (6)
C3—C21.531 (3)C6GB—C5GB1.465 (6)
C3—H310.9900C6GB—C7GB1.563 (6)
C3—H320.9900C1GB—C1GBi1.319 (9)
C9—H90.9500C1GB—C2GBi1.339 (5)
C2GA—C3GA1.392 (3)C1GB—C6GBi1.339 (5)
C2GA—C7GA1.504 (3)C1GB—C5GBi1.359 (7)
C18—C171.393 (3)C1GB—C4GBi1.448 (5)
C18—H180.9500C1GB—N1GBi1.448 (5)
C12—H120.9500C1GB—C3GBi1.533 (7)
C2—H210.9900C3GB—C8GBi1.433 (8)
C2—H220.9900C3GB—C2GBi1.446 (5)
C17—C161.379 (3)C3GB—C6GBi1.446 (5)
C17—H170.9500C3GB—C1GBi1.533 (7)
C6—C51.527 (3)C5GB—C1GBi1.359 (7)
C6—H610.9900C5GB—C7GB1.674 (8)
C6—H620.9900C7GB—C8GB1.395 (8)
C16—C151.378 (3)C8GB—C3GBi1.433 (8)
C10—O1—H1113.5 (17)H7A1—C7GA—H7A2109.5
C8—C7—C12116.41 (19)C2GA—C7GA—H7A3109.5
C8—C7—C1121.68 (18)H7A1—C7GA—H7A3109.5
C12—C7—C1121.83 (19)H7A2—C7GA—H7A3109.5
C16—O2—H2115.3 (18)C4GA—C3GA—C2GA120.9 (3)
C9—C8—C7122.32 (19)C4GA—C3GA—H3GA119.6
C9—C8—H8118.8C2GA—C3GA—H3GA119.6
C7—C8—H8118.8C4GA—C5GA—C6GA121.1 (2)
C1GA—N1GA—H1A1113.7 (18)C4GA—C5GA—H5GA119.4
C1GA—N1GA—H1A2112.4 (18)C6GA—C5GA—H5GA119.4
H1A1—N1GA—H1A2110 (3)C6GA—C8GA—H8A1109.5
C7—C1—C13109.93 (17)C6GA—C8GA—H8A2109.5
C7—C1—C2111.22 (17)H8A1—C8GA—H8A2109.5
C13—C1—C2108.86 (15)C6GA—C8GA—H8A3109.5
C7—C1—C6111.09 (16)H8A1—C8GA—H8A3109.5
C13—C1—C6108.95 (17)H8A2—C8GA—H8A3109.5
C2—C1—C6106.69 (16)C5GA—C4GA—C3GA120.0 (2)
C15—C14—C13122.3 (2)C5GA—C4GA—H4GA120.0
C15—C14—H14118.8C3GA—C4GA—H4GA120.0
C13—C14—H14118.8C5GB—N1GB—C3GB122.9 (3)
C18—C13—C14116.2 (2)C5GB—N1GB—C1GBi58.6 (3)
C18—C13—C1123.73 (19)C3GB—N1GB—C1GBi64.6 (3)
C14—C13—C1120.02 (18)C1GBi—C6GB—C1GB57.0 (4)
C11—C10—C9119.6 (2)C1GBi—C6GB—C3GBi121.5 (4)
C11—C10—O1117.89 (18)C1GB—C6GB—C3GBi64.6 (3)
C9—C10—O1122.5 (2)C1GBi—C6GB—C8GB179.3 (3)
C2GA—C1GA—C6GA121.0 (2)C1GB—C6GB—C8GB123.5 (4)
C2GA—C1GA—N1GA120.1 (2)C3GBi—C6GB—C8GB59.0 (3)
C6GA—C1GA—N1GA118.8 (2)C1GBi—C6GB—C5GB57.8 (3)
C10—C11—C12120.1 (2)C1GB—C6GB—C5GB114.6 (4)
C10—C11—H11119.9C3GBi—C6GB—C5GB179.2 (4)
C12—C11—H11119.9C8GB—C6GB—C5GB121.7 (4)
C4—C3—C2111.45 (19)C1GBi—C6GB—C7GB124.6 (3)
C4—C3—H31109.3C1GB—C6GB—C7GB178.3 (4)
C2—C3—H31109.3C3GBi—C6GB—C7GB113.7 (4)
C4—C3—H32109.3C8GB—C6GB—C7GB54.8 (3)
C2—C3—H32109.3C5GB—C6GB—C7GB67.0 (3)
H31—C3—H32108.0C1GBi—C1GB—C2GBi64.7 (4)
C10—C9—C8119.5 (2)C1GBi—C1GB—C6GBi64.7 (4)
C10—C9—H9120.2C2GBi—C1GB—C6GBi0.0 (3)
C8—C9—H9120.2C1GBi—C1GB—C5GBi130.2 (7)
C3GA—C2GA—C1GA118.7 (2)C2GBi—C1GB—C5GBi65.7 (4)
C3GA—C2GA—C7GA120.5 (2)C6GBi—C1GB—C5GBi65.7 (4)
C1GA—C2GA—C7GA120.8 (2)C1GBi—C1GB—C6GB58.3 (4)
C13—C18—C17122.2 (2)C2GBi—C1GB—C6GB123.0 (4)
C13—C18—H18118.9C6GBi—C1GB—C6GB123.0 (4)
C17—C18—H18118.9C5GBi—C1GB—C6GB170.3 (5)
C11—C12—C7122.0 (2)C1GBi—C1GB—C4GBi173.1 (6)
C11—C12—H12119.0C2GBi—C1GB—C4GBi121.6 (4)
C7—C12—H12119.0C6GBi—C1GB—C4GBi121.6 (4)
C3—C2—C1112.85 (17)C5GBi—C1GB—C4GBi55.9 (3)
C3—C2—H21109.0C6GB—C1GB—C4GBi115.3 (4)
C1—C2—H21109.0C1GBi—C1GB—N1GBi173.1 (6)
C3—C2—H22109.0C2GBi—C1GB—N1GBi121.6 (4)
C1—C2—H22109.0C6GBi—C1GB—N1GBi121.6 (4)
H21—C2—H22107.8C5GBi—C1GB—N1GBi55.9 (3)
C16—C17—C18119.8 (2)C6GB—C1GB—N1GBi115.3 (4)
C16—C17—H17120.1C4GBi—C1GB—N1GBi0.00 (4)
C18—C17—H17120.1C1GBi—C1GB—C3GBi116.7 (6)
C5—C6—C1112.97 (18)C2GBi—C1GB—C3GBi176.1 (4)
C5—C6—H61109.0C6GBi—C1GB—C3GBi176.1 (4)
C1—C6—H61109.0C5GBi—C1GB—C3GBi112.5 (4)
C5—C6—H62109.0C6GB—C1GB—C3GBi58.4 (3)
C1—C6—H62109.0C4GBi—C1GB—C3GBi56.9 (3)
H61—C6—H62107.8N1GBi—C1GB—C3GBi56.9 (3)
O2—C16—C15117.7 (2)N1GB—C3GB—C8GBi174.3 (5)
O2—C16—C17122.7 (2)N1GB—C3GB—C2GBi115.5 (4)
C15—C16—C17119.6 (2)C8GBi—C3GB—C2GBi61.1 (3)
C14—C15—C16119.9 (2)N1GB—C3GB—C6GBi115.5 (4)
C14—C15—H15120.1C8GBi—C3GB—C6GBi61.1 (3)
C16—C15—H15120.1C2GBi—C3GB—C6GBi0.00 (17)
C4—C5—C6110.81 (18)N1GB—C3GB—C1GBi58.6 (3)
C4—C5—H51109.5C8GBi—C3GB—C1GBi117.9 (4)
C6—C5—H51109.5C2GBi—C3GB—C1GBi56.9 (3)
C4—C5—H52109.5C6GBi—C3GB—C1GBi56.9 (3)
C6—C5—H52109.5N1GB—C5GB—C1GBi65.5 (3)
H51—C5—H52108.1N1GB—C5GB—C6GB121.9 (4)
C5GA—C6GA—C1GA118.3 (2)C1GBi—C5GB—C6GB56.5 (3)
C5GA—C6GA—C8GA121.1 (2)N1GB—C5GB—C7GB174.2 (4)
C1GA—C6GA—C8GA120.6 (2)C1GBi—C5GB—C7GB115.6 (4)
C5—C4—C3112.16 (19)C6GB—C5GB—C7GB59.3 (3)
C5—C4—H41109.2C8GB—C7GB—C6GB58.9 (3)
C3—C4—H41109.2C8GB—C7GB—C5GB112.5 (4)
C5—C4—H42109.2C6GB—C7GB—C5GB53.7 (3)
C3—C4—H42109.2C7GB—C8GB—C3GBi126.0 (5)
H41—C4—H42107.9C7GB—C8GB—C6GB66.3 (4)
C2GA—C7GA—H7A1109.5C3GBi—C8GB—C6GB59.9 (3)
C2GA—C7GA—H7A2109.5
C12—C7—C8—C90.8 (3)C7GB—C6GB—C1GB—C6GBi168 (10)
C1—C7—C8—C9176.06 (19)C1GBi—C6GB—C1GB—C5GBi153 (3)
C8—C7—C1—C1388.0 (2)C3GBi—C6GB—C1GB—C5GBi23 (2)
C12—C7—C1—C1388.7 (2)C8GB—C6GB—C1GB—C5GBi27 (3)
C8—C7—C1—C232.7 (3)C5GB—C6GB—C1GB—C5GBi157 (2)
C12—C7—C1—C2150.7 (2)C7GB—C6GB—C1GB—C5GBi16 (12)
C8—C7—C1—C6151.4 (2)C1GBi—C6GB—C1GB—C4GBi177.1 (6)
C12—C7—C1—C632.0 (3)C3GBi—C6GB—C1GB—C4GBi1.4 (3)
C15—C14—C13—C180.3 (3)C8GB—C6GB—C1GB—C4GBi2.3 (5)
C15—C14—C13—C1179.49 (19)C5GB—C6GB—C1GB—C4GBi178.4 (3)
C7—C1—C13—C180.9 (3)C7GB—C6GB—C1GB—C4GBi9 (11)
C2—C1—C13—C18123.0 (2)C1GBi—C6GB—C1GB—N1GBi177.1 (6)
C6—C1—C13—C18121.0 (2)C3GBi—C6GB—C1GB—N1GBi1.4 (3)
C7—C1—C13—C14178.84 (18)C8GB—C6GB—C1GB—N1GBi2.3 (5)
C2—C1—C13—C1456.8 (2)C5GB—C6GB—C1GB—N1GBi178.4 (3)
C6—C1—C13—C1459.2 (2)C7GB—C6GB—C1GB—N1GBi9 (11)
C9—C10—C11—C121.0 (3)C1GBi—C6GB—C1GB—C3GBi175.7 (4)
O1—C10—C11—C12177.78 (19)C8GB—C6GB—C1GB—C3GBi3.7 (4)
C11—C10—C9—C81.6 (3)C5GB—C6GB—C1GB—C3GBi179.8 (3)
O1—C10—C9—C8177.13 (19)C7GB—C6GB—C1GB—C3GBi7 (10)
C7—C8—C9—C100.7 (3)C5GB—N1GB—C3GB—C8GBi59 (5)
C6GA—C1GA—C2GA—C3GA1.4 (3)C1GBi—N1GB—C3GB—C8GBi53 (5)
N1GA—C1GA—C2GA—C3GA178.2 (2)C5GB—N1GB—C3GB—C2GBi7.8 (5)
C6GA—C1GA—C2GA—C7GA179.6 (2)C1GBi—N1GB—C3GB—C2GBi1.4 (3)
N1GA—C1GA—C2GA—C7GA2.8 (3)C5GB—N1GB—C3GB—C6GBi7.8 (5)
C14—C13—C18—C170.2 (3)C1GBi—N1GB—C3GB—C6GBi1.4 (3)
C1—C13—C18—C17179.95 (19)C5GB—N1GB—C3GB—C1GBi6.4 (4)
C10—C11—C12—C70.6 (3)C3GB—N1GB—C5GB—C1GBi6.7 (4)
C8—C7—C12—C111.4 (3)C3GB—N1GB—C5GB—C6GB8.5 (5)
C1—C7—C12—C11175.4 (2)C1GBi—N1GB—C5GB—C6GB1.8 (3)
C4—C3—C2—C156.0 (2)C3GB—N1GB—C5GB—C7GB109 (5)
C7—C1—C2—C365.0 (2)C1GBi—N1GB—C5GB—C7GB102 (5)
C13—C1—C2—C3173.71 (18)C1GBi—C6GB—C5GB—N1GB1.9 (3)
C6—C1—C2—C356.3 (2)C1GB—C6GB—C5GB—N1GB6.4 (5)
C13—C18—C17—C160.6 (3)C3GBi—C6GB—C5GB—N1GB20 (26)
C7—C1—C6—C564.2 (2)C8GB—C6GB—C5GB—N1GB177.4 (3)
C13—C1—C6—C5174.57 (16)C7GB—C6GB—C5GB—N1GB173.3 (4)
C2—C1—C6—C557.2 (2)C1GB—C6GB—C5GB—C1GBi4.5 (4)
C18—C17—C16—O2178.1 (2)C3GBi—C6GB—C5GB—C1GBi18 (26)
C18—C17—C16—C150.6 (3)C8GB—C6GB—C5GB—C1GBi179.4 (4)
C13—C14—C15—C160.3 (3)C7GB—C6GB—C5GB—C1GBi175.3 (3)
O2—C16—C15—C14178.6 (2)C1GBi—C6GB—C5GB—C7GB175.3 (3)
C17—C16—C15—C140.1 (3)C1GB—C6GB—C5GB—C7GB179.8 (3)
C1—C6—C5—C457.2 (2)C3GBi—C6GB—C5GB—C7GB167 (26)
C2GA—C1GA—C6GA—C5GA1.1 (3)C8GB—C6GB—C5GB—C7GB4.1 (4)
N1GA—C1GA—C6GA—C5GA177.9 (2)C1GBi—C6GB—C7GB—C8GB179.4 (4)
C2GA—C1GA—C6GA—C8GA178.6 (2)C1GB—C6GB—C7GB—C8GB11 (10)
N1GA—C1GA—C6GA—C8GA1.8 (3)C3GBi—C6GB—C7GB—C8GB4.1 (4)
C6—C5—C4—C353.7 (3)C5GB—C6GB—C7GB—C8GB175.7 (4)
C2—C3—C4—C553.2 (2)C1GBi—C6GB—C7GB—C5GB4.9 (4)
C1GA—C2GA—C3GA—C4GA1.0 (4)C1GB—C6GB—C7GB—C5GB173 (10)
C7GA—C2GA—C3GA—C4GA180.0 (2)C3GBi—C6GB—C7GB—C5GB179.8 (3)
C1GA—C6GA—C5GA—C4GA0.3 (4)C8GB—C6GB—C7GB—C5GB175.7 (4)
C8GA—C6GA—C5GA—C4GA179.4 (3)N1GB—C5GB—C7GB—C8GB107 (5)
C6GA—C5GA—C4GA—C3GA0.1 (4)C1GBi—C5GB—C7GB—C8GB8.3 (6)
C2GA—C3GA—C4GA—C5GA0.2 (4)C6GB—C5GB—C7GB—C8GB3.9 (4)
C3GBi—C6GB—C1GB—C1GBi175.7 (4)N1GB—C5GB—C7GB—C6GB103 (5)
C8GB—C6GB—C1GB—C1GBi179.4 (4)C1GBi—C5GB—C7GB—C6GB4.4 (3)
C5GB—C6GB—C1GB—C1GBi4.5 (4)C6GB—C7GB—C8GB—C3GBi4.6 (5)
C7GB—C6GB—C1GB—C1GBi168 (10)C5GB—C7GB—C8GB—C3GBi8.4 (7)
C1GBi—C6GB—C1GB—C2GBi0.000 (1)C5GB—C7GB—C8GB—C6GB3.7 (3)
C3GBi—C6GB—C1GB—C2GBi175.7 (4)C1GBi—C6GB—C8GB—C7GB42 (31)
C8GB—C6GB—C1GB—C2GBi179.4 (4)C1GB—C6GB—C8GB—C7GB179.6 (4)
C5GB—C6GB—C1GB—C2GBi4.5 (4)C3GBi—C6GB—C8GB—C7GB175.7 (4)
C7GB—C6GB—C1GB—C2GBi168 (10)C5GB—C6GB—C8GB—C7GB4.6 (4)
C1GBi—C6GB—C1GB—C6GBi0.000 (1)C1GBi—C6GB—C8GB—C3GBi133 (31)
C3GBi—C6GB—C1GB—C6GBi175.7 (4)C1GB—C6GB—C8GB—C3GBi3.9 (4)
C8GB—C6GB—C1GB—C6GBi179.4 (4)C5GB—C6GB—C8GB—C3GBi179.7 (3)
C5GB—C6GB—C1GB—C6GBi4.5 (4)C7GB—C6GB—C8GB—C3GBi175.7 (4)
Symmetry code: (i) x+3, y+1, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···N1GA0.96 (1)1.85 (1)2.804 (3)170 (3)
O2—H2···O1ii0.99 (1)1.81 (2)2.759 (2)160 (3)
N1GA—H1A1···N1GB0.95 (2)2.52 (2)3.392 (3)154 (2)
Symmetry code: (ii) x+2, y+1, z+1.
(dc26x2.5) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 2,3-xylidine top
Crystal data top
C18H20O2/2.5(C8H11N)Z = 4
Mr = 571.29F(000) = 1236
Triclinic, P1Dx = 1.166 Mg m3
Dm = N/A Mg m3
Dm measured by not measured
a = 7.885 (1) ÅMelting point: Not measured K
b = 10.026 (1) ÅMo Kα radiation, λ = 0.71069 Å
c = 43.761 (3) ŵ = 0.07 mm1
α = 94.661 (1)°T = 173 K
β = 91.539 (2)°Prism, colourless
γ = 109.02 (1)°0.47 × 0.30 × 0.10 mm
V = 3254.6 (6) Å3
Data collection top
Nonius Kappa CCD
diffractometer
5565 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 24.4°, θmin = 2.2°
0.5° φ scans and ω scansh = 88
10828 measured reflectionsk = 1111
7844 independent reflectionsl = 4350
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.189H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.565 w = 1/[σ2(Fo2) + (0.2P)2]
where P = (Fo2 + 2Fc2)/3
S = 2.50(Δ/σ)max = 0.040
7844 reflectionsΔρmax = 2.01 e Å3
609 parametersΔρmin = 1.04 e Å3
3 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.002 (7)
Special details top

Experimental. Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 55 mm; combination of φ and ω scans of 0.5°, 80 s per °, 2 iterations.

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*/Ueq
O2X0.0568 (7)0.9608 (5)0.38811 (13)0.0346 (15)
H2X0.015 (15)1.006 (13)0.377 (3)0.14 (6)*
O1X0.2552 (7)1.2477 (6)0.60021 (13)0.0399 (15)
H1X0.133 (6)1.212 (9)0.607 (2)0.06 (3)*
N1GC0.0762 (8)1.1054 (6)0.34703 (17)0.0386 (19)
C15X0.2188 (9)1.1806 (7)0.4176 (2)0.033 (2)
H15X0.15551.22980.40670.039*
C14X0.3478 (8)1.2529 (7)0.44143 (19)0.0280 (19)
H14X0.36821.35070.44700.034*
C3X0.7922 (9)1.4408 (8)0.45104 (19)0.032 (2)
H3X10.71591.39980.43200.039*
H3X20.85061.54340.44940.039*
C1X0.5819 (9)1.2646 (7)0.48415 (17)0.0242 (18)
C7X0.4899 (9)1.2577 (7)0.51427 (19)0.031 (2)
C10X0.3249 (10)1.2445 (7)0.5711 (2)0.033 (2)
C16X0.1855 (9)1.0373 (8)0.41012 (18)0.0276 (19)
C17X0.2801 (10)0.9684 (8)0.42534 (19)0.032 (2)
H17X0.25900.87050.41990.038*
C8X0.5864 (10)1.3236 (8)0.5420 (2)0.031 (2)
H8X0.71171.37200.54150.037*
C2GC0.1659 (10)1.3076 (8)0.3670 (2)0.039 (2)
C2X0.6735 (10)1.4215 (8)0.4785 (2)0.035 (2)
H2X10.57951.46520.47500.042*
H2X20.74771.47230.49710.042*
C6X0.7347 (9)1.2005 (8)0.4872 (2)0.034 (2)
H6X10.81341.24840.50560.040*
H6X20.68161.09900.49030.040*
C9X0.5081 (10)1.3213 (8)0.5698 (2)0.035 (2)
H9X0.57711.37110.58780.042*
C11X0.2234 (9)1.1772 (7)0.54547 (19)0.0290 (19)
H11X0.09951.12550.54660.035*
C1GC0.0382 (10)1.2572 (8)0.3542 (2)0.033 (2)
C18X0.4084 (9)1.0415 (7)0.44898 (18)0.0275 (18)
H18X0.47100.99160.45980.033*
C13X0.4449 (9)1.1845 (8)0.45684 (19)0.031 (2)
C12X0.3052 (9)1.1853 (8)0.5170 (2)0.034 (2)
H12X0.23291.14010.49900.041*
C4GC0.0429 (13)1.5486 (9)0.3664 (2)0.051 (3)
H4GC0.06991.64790.37080.061*
C3GC0.1199 (12)1.4562 (8)0.3729 (2)0.044 (2)
H3GC0.20561.49350.38180.052*
C6GC0.1281 (10)1.3479 (8)0.3471 (2)0.038 (2)
C5GC0.1667 (12)1.4944 (9)0.3534 (2)0.048 (2)
H5GC0.27991.55730.34850.058*
C4X0.9342 (10)1.3724 (8)0.4535 (2)0.042 (2)
H4X11.02251.42300.47060.051*
H4X20.99841.37880.43430.051*
C7GC0.3441 (12)1.2118 (9)0.3743 (2)0.055 (3)
H7C10.39911.14570.35630.083*
H7C20.42141.26800.38010.083*
H7C30.32971.15850.39150.083*
C8GC0.2693 (11)1.2911 (10)0.3330 (2)0.055 (3)
H8C10.30801.23630.34760.083*
H8C20.37291.37060.32810.083*
H8C30.21741.22990.31410.083*
C5X0.8481 (10)1.2142 (8)0.4595 (2)0.040 (2)
H5X10.77221.16100.44120.048*
H5X20.94401.17250.46300.048*
O2Y0.8929 (8)0.5824 (7)0.23675 (18)0.060 (2)
H2Y0.90 (2)0.526 (18)0.254 (3)0.21 (9)*
C15Y0.7387 (11)0.3789 (9)0.2014 (2)0.046 (2)
H15Y0.79660.32200.21080.055*
C17Y0.6866 (11)0.5972 (9)0.1971 (2)0.053 (3)
H17Y0.70840.69330.20450.064*
C14Y0.6115 (11)0.3213 (9)0.1757 (2)0.047 (2)
H14Y0.58300.22390.16880.057*
C18Y0.5727 (12)0.5402 (10)0.1727 (3)0.057 (3)
H18Y0.51870.59890.16300.069*
C16Y0.7741 (11)0.5172 (9)0.2119 (2)0.049 (3)
C1Y0.4139 (13)0.3416 (11)0.1307 (3)0.068 (3)
C13Y0.5296 (10)0.4002 (10)0.1608 (2)0.047 (3)
C2Y0.3142 (13)0.1793 (12)0.1292 (3)0.073 (4)
H2Y10.25110.14610.10880.087*
H2Y20.40370.13040.13160.087*
C6Y0.2556 (13)0.4057 (14)0.1284 (3)0.076 (4)
H6Y10.30780.51040.12990.091*
H6Y20.19130.37380.10800.091*
C8GD0.552 (2)0.8235 (17)0.0041 (4)0.120 (5)*
N1GA0.0375 (8)0.4119 (6)0.27087 (18)0.043 (2)
C1GA0.0058 (10)0.2632 (8)0.2645 (2)0.036 (2)
C2GA0.1769 (10)0.1761 (9)0.2720 (2)0.038 (2)
C6GA0.1093 (11)0.2044 (8)0.2501 (2)0.045 (2)
C4GA0.1034 (14)0.0284 (9)0.2531 (3)0.063 (3)
H4GA0.13660.12850.24920.075*
C3GA0.2193 (12)0.0321 (9)0.2666 (2)0.049 (3)
H3GA0.33200.02750.27240.059*
C7GA0.3097 (11)0.2448 (11)0.2860 (3)0.062 (3)
H7A10.42040.17040.29030.094*
H7A20.33770.30500.27150.094*
H7A30.25530.30240.30510.094*
C5GA0.0624 (12)0.0581 (9)0.2450 (2)0.054 (3)
H5GA0.14440.01700.23610.065*
C8GA0.2956 (11)0.2983 (10)0.2414 (3)0.062 (3)
H8A10.36410.23810.23360.092*
H8A20.36020.35900.25960.092*
H8A30.28100.35760.22550.092*
N1GB0.5326 (8)0.8483 (7)0.34991 (18)0.044 (2)
C2GB0.5781 (10)0.7107 (8)0.3035 (2)0.043 (3)
C1GB0.4843 (10)0.7902 (7)0.3193 (2)0.035 (2)
C5GB0.3022 (10)0.7659 (8)0.2720 (2)0.042 (2)
H5GB0.20790.78420.26100.050*
C6GB0.3441 (9)0.8180 (8)0.3033 (2)0.036 (2)
C3GB0.5341 (11)0.6617 (8)0.2731 (2)0.042 (2)
H3GB0.59920.60840.26280.051*
C4GB0.3988 (12)0.6883 (9)0.2573 (2)0.051 (3)
H4GB0.37070.65370.23630.062*
C7GB0.7345 (12)0.6824 (10)0.3203 (3)0.059 (3)
H7B10.79170.63280.30580.088*
H7B20.68900.62370.33700.088*
H7B30.82280.77270.32870.088*
C8GB0.2410 (11)0.9039 (10)0.3188 (2)0.054 (3)
H8B10.14060.90310.30500.081*
H8B20.32061.00170.32380.081*
H8B30.19440.86290.33770.081*
C3Y0.1760 (12)0.1376 (11)0.1543 (3)0.071 (4)
H3Y10.11510.03370.15170.086*
H3Y20.24040.16240.17480.086*
C5Y0.1199 (12)0.3643 (12)0.1532 (3)0.071 (3)
H5Y10.18240.40140.17360.085*
H5Y20.02700.40950.15030.085*
C4Y0.0331 (13)0.2126 (14)0.1528 (3)0.084 (4)
H4Y10.04480.17650.13380.101*
H4Y20.04340.19160.17050.101*
N1GD0.7625 (18)0.6773 (16)0.0089 (4)0.145 (5)*
C1GD0.8242 (16)0.8047 (10)0.0109 (3)0.142 (6)*
C2GD0.9972 (14)0.8508 (13)0.0245 (3)0.175 (8)*
C3GD1.0520 (11)0.9696 (14)0.0458 (3)0.121 (5)*
C4GD0.9337 (16)1.0423 (11)0.0534 (3)0.152 (7)*
C5GD0.7607 (14)0.9962 (11)0.0398 (3)0.123 (5)*
C6GD0.7059 (11)0.8774 (11)0.0185 (2)0.085 (4)*
C1GE0.2611 (17)0.8023 (14)0.1545 (4)0.114 (5)*
C2GE0.443 (2)0.8655 (17)0.1628 (3)0.35 (2)*
C3GE0.5684 (13)0.8879 (16)0.1404 (5)0.144 (6)*
C4GE0.512 (2)0.8469 (19)0.1097 (4)0.303 (17)*
C5GE0.330 (3)0.784 (2)0.1014 (3)0.194 (9)*
C6GE0.2047 (16)0.7613 (15)0.1238 (4)0.187 (9)*
C7Y0.5469 (8)0.3753 (6)0.10601 (16)0.079 (3)*
C8Y0.5746 (7)0.4946 (7)0.09018 (14)0.186 (9)*
C9Y0.7059 (9)0.5267 (7)0.06884 (14)0.228 (12)*
C10Y0.8096 (8)0.4396 (7)0.06333 (15)0.191 (9)*
C11Y0.7819 (9)0.3202 (7)0.07917 (17)0.141 (6)*
C12Y0.6505 (11)0.2881 (6)0.10051 (19)0.105 (4)*
C8GE0.0258 (13)0.7083 (14)0.1269 (3)0.218 (11)*
C7GD1.1050 (18)0.7510 (12)0.0146 (3)0.202 (10)*
O1Y0.9406 (10)0.4720 (9)0.04199 (17)0.194 (6)*
N1GE0.1610 (14)0.7895 (12)0.1828 (3)0.182 (7)*
C7GE0.5029 (15)0.9148 (11)0.1908 (3)0.186 (9)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O2X0.037 (3)0.028 (3)0.035 (4)0.008 (2)0.006 (3)0.004 (2)
O1X0.050 (4)0.046 (3)0.020 (4)0.011 (3)0.008 (3)0.003 (2)
N1GC0.036 (4)0.035 (4)0.044 (5)0.012 (3)0.009 (3)0.006 (3)
C15X0.026 (4)0.025 (4)0.049 (6)0.011 (3)0.001 (4)0.007 (4)
C14X0.023 (4)0.025 (4)0.039 (6)0.013 (3)0.003 (4)0.002 (3)
C3X0.032 (4)0.037 (4)0.026 (6)0.008 (3)0.005 (4)0.007 (3)
C1X0.029 (4)0.024 (4)0.015 (5)0.004 (3)0.000 (3)0.002 (3)
C7X0.032 (4)0.022 (4)0.041 (6)0.010 (3)0.001 (4)0.011 (3)
C10X0.046 (5)0.025 (4)0.029 (6)0.013 (4)0.001 (4)0.008 (3)
C16X0.021 (4)0.038 (4)0.020 (5)0.004 (3)0.002 (3)0.000 (3)
C17X0.039 (4)0.025 (4)0.031 (6)0.008 (3)0.001 (4)0.007 (3)
C8X0.028 (4)0.033 (4)0.031 (6)0.008 (3)0.000 (4)0.005 (3)
C2GC0.041 (5)0.037 (5)0.035 (6)0.008 (4)0.006 (4)0.002 (4)
C2X0.041 (4)0.030 (4)0.032 (6)0.010 (4)0.010 (4)0.003 (3)
C6X0.032 (4)0.033 (4)0.036 (6)0.011 (3)0.007 (4)0.003 (3)
C9X0.038 (4)0.028 (4)0.037 (6)0.008 (3)0.007 (4)0.002 (3)
C11X0.029 (4)0.031 (4)0.028 (6)0.010 (3)0.007 (4)0.000 (3)
C1GC0.042 (5)0.029 (4)0.030 (6)0.012 (4)0.009 (4)0.010 (3)
C18X0.031 (4)0.034 (4)0.015 (5)0.009 (3)0.006 (3)0.001 (3)
C13X0.026 (4)0.032 (4)0.032 (6)0.003 (3)0.003 (4)0.012 (3)
C12X0.031 (4)0.031 (4)0.038 (6)0.007 (3)0.007 (4)0.003 (3)
C4GC0.065 (6)0.038 (5)0.048 (7)0.014 (5)0.008 (5)0.005 (4)
C3GC0.064 (6)0.035 (5)0.035 (6)0.023 (4)0.001 (4)0.000 (4)
C6GC0.038 (4)0.032 (5)0.040 (6)0.007 (4)0.009 (4)0.004 (4)
C5GC0.049 (5)0.046 (5)0.041 (7)0.003 (4)0.001 (5)0.015 (4)
C4X0.032 (4)0.041 (5)0.047 (7)0.003 (4)0.009 (4)0.004 (4)
C7GC0.069 (6)0.048 (6)0.040 (7)0.011 (5)0.001 (5)0.003 (4)
C8GC0.049 (5)0.063 (6)0.056 (8)0.020 (5)0.005 (5)0.012 (5)
C5X0.040 (4)0.043 (5)0.042 (7)0.019 (4)0.015 (4)0.007 (4)
O2Y0.055 (4)0.057 (4)0.059 (6)0.014 (3)0.028 (4)0.020 (4)
C15Y0.046 (5)0.051 (6)0.036 (7)0.014 (4)0.016 (4)0.007 (4)
C17Y0.049 (5)0.044 (5)0.067 (8)0.023 (4)0.022 (5)0.016 (5)
C14Y0.042 (5)0.050 (5)0.046 (7)0.013 (4)0.007 (5)0.008 (4)
C18Y0.055 (6)0.069 (7)0.061 (8)0.043 (5)0.001 (5)0.007 (5)
C16Y0.042 (5)0.043 (5)0.061 (8)0.014 (4)0.000 (5)0.002 (4)
C1Y0.059 (6)0.080 (8)0.060 (9)0.022 (6)0.023 (6)0.015 (6)
C13Y0.031 (4)0.055 (6)0.048 (7)0.010 (4)0.004 (4)0.015 (4)
C2Y0.057 (6)0.085 (8)0.070 (10)0.026 (6)0.024 (6)0.034 (6)
C6Y0.050 (6)0.128 (10)0.042 (9)0.025 (6)0.021 (6)0.015 (6)
N1GA0.041 (4)0.025 (4)0.062 (6)0.008 (3)0.015 (4)0.006 (3)
C1GA0.036 (4)0.037 (5)0.032 (6)0.010 (4)0.004 (4)0.005 (4)
C2GA0.032 (4)0.054 (5)0.022 (6)0.004 (4)0.005 (4)0.006 (4)
C6GA0.037 (5)0.033 (5)0.057 (7)0.003 (4)0.001 (4)0.001 (4)
C4GA0.071 (7)0.027 (5)0.082 (9)0.006 (5)0.010 (6)0.007 (5)
C3GA0.050 (5)0.036 (5)0.045 (7)0.009 (4)0.006 (5)0.012 (4)
C7GA0.034 (5)0.091 (8)0.059 (8)0.009 (5)0.021 (5)0.027 (6)
C5GA0.057 (6)0.039 (5)0.060 (8)0.011 (5)0.001 (5)0.005 (4)
C8GA0.041 (5)0.050 (6)0.083 (9)0.000 (4)0.019 (5)0.003 (5)
N1GB0.035 (4)0.036 (4)0.049 (6)0.004 (3)0.012 (4)0.003 (3)
C2GB0.030 (4)0.029 (4)0.067 (8)0.004 (4)0.001 (4)0.022 (4)
C1GB0.034 (4)0.022 (4)0.039 (6)0.003 (3)0.009 (4)0.005 (3)
C5GB0.039 (5)0.033 (5)0.049 (7)0.004 (4)0.006 (4)0.013 (4)
C6GB0.027 (4)0.032 (4)0.051 (7)0.008 (3)0.008 (4)0.014 (4)
C3GB0.052 (5)0.031 (4)0.040 (7)0.007 (4)0.012 (5)0.008 (4)
C4GB0.055 (5)0.033 (5)0.054 (7)0.001 (4)0.007 (5)0.011 (4)
C7GB0.056 (6)0.047 (5)0.074 (9)0.017 (4)0.001 (5)0.013 (5)
C8GB0.045 (5)0.054 (6)0.058 (8)0.009 (4)0.003 (5)0.014 (5)
C3Y0.042 (5)0.069 (7)0.093 (11)0.013 (5)0.000 (6)0.026 (6)
C5Y0.045 (6)0.095 (9)0.068 (10)0.025 (6)0.022 (6)0.018 (6)
C4Y0.046 (6)0.108 (10)0.084 (11)0.014 (6)0.003 (6)0.025 (7)
Geometric parameters (Å, º) top
O2X—C16X1.366 (9)N1GA—C1GA1.418 (10)
O1X—C10X1.403 (10)C1GA—C6GA1.374 (12)
N1GC—C1GC1.458 (10)C1GA—C2GA1.412 (11)
C15X—C16X1.383 (10)C2GA—C3GA1.370 (12)
C15X—C14X1.411 (11)C2GA—C7GA1.543 (13)
C14X—C13X1.379 (10)C6GA—C5GA1.389 (12)
C3X—C4X1.497 (11)C6GA—C8GA1.541 (11)
C3X—C2X1.528 (11)C4GA—C3GA1.374 (14)
C1X—C7X1.517 (11)C4GA—C5GA1.386 (13)
C1X—C2X1.546 (10)N1GB—C1GB1.408 (11)
C1X—C6X1.546 (10)C2GB—C3GB1.375 (12)
C1X—C13X1.565 (10)C2GB—C1GB1.408 (12)
C7X—C8X1.406 (11)C2GB—C7GB1.535 (12)
C7X—C12X1.413 (10)C1GB—C6GB1.407 (11)
C10X—C11X1.353 (11)C5GB—C4GB1.389 (13)
C10X—C9X1.403 (10)C5GB—C6GB1.416 (13)
C16X—C17X1.364 (10)C6GB—C8GB1.501 (13)
C17X—C18X1.403 (10)C3GB—C4GB1.363 (12)
C8X—C9X1.377 (11)C3Y—C4Y1.548 (15)
C2GC—C1GC1.378 (11)C5Y—C4Y1.449 (16)
C2GC—C3GC1.413 (11)N1GD—C1GD1.419 (17)
C2GC—C7GC1.481 (12)C1GD—C2GD1.3900
C6X—C5X1.514 (11)C1GD—C6GD1.3900
C11X—C12X1.414 (11)C2GD—C3GD1.3900
C1GC—C6GC1.390 (11)C2GD—C7GD1.554 (14)
C18X—C13X1.380 (10)C3GD—C4GD1.3900
C4GC—C3GC1.369 (12)C4GD—C5GD1.3900
C4GC—C5GC1.378 (13)C5GD—C6GD1.3900
C6GC—C5GC1.402 (12)C1GE—C2GE1.3900
C6GC—C8GC1.530 (12)C1GE—C6GE1.3900
C4X—C5X1.555 (11)C1GE—N1GE1.478 (14)
O2Y—C16Y1.383 (11)C2GE—C7GE1.297 (15)
C15Y—C16Y1.360 (12)C2GE—C3GE1.3900
C15Y—C14Y1.434 (12)C3GE—C4GE1.3900
C17Y—C18Y1.339 (13)C4GE—C5GE1.3900
C17Y—C16Y1.400 (12)C5GE—C6GE1.3900
C14Y—C13Y1.365 (13)C6GE—C8GE1.351 (15)
C18Y—C13Y1.385 (12)C7Y—C8Y1.3900
C1Y—C7Y1.506 (13)C7Y—C12Y1.3900
C1Y—C13Y1.542 (13)C8Y—C9Y1.3900
C1Y—C2Y1.554 (15)C9Y—C10Y1.3900
C1Y—C6Y1.583 (15)C10Y—O1Y1.3885
C2Y—C3Y1.550 (16)C10Y—C11Y1.3900
C6Y—C5Y1.529 (16)C11Y—C12Y1.3900
C8GD—C6GD1.280 (17)
C16X—C15X—C14X119.2 (7)C6GA—C1GA—C2GA120.3 (7)
C13X—C14X—C15X121.3 (7)C6GA—C1GA—N1GA121.9 (7)
C4X—C3X—C2X112.8 (7)C2GA—C1GA—N1GA117.7 (7)
C7X—C1X—C2X109.3 (6)C3GA—C2GA—C1GA118.4 (8)
C7X—C1X—C6X108.6 (6)C3GA—C2GA—C7GA122.0 (7)
C2X—C1X—C6X106.2 (6)C1GA—C2GA—C7GA119.6 (7)
C7X—C1X—C13X111.1 (6)C1GA—C6GA—C5GA119.7 (8)
C2X—C1X—C13X110.6 (6)C1GA—C6GA—C8GA120.9 (7)
C6X—C1X—C13X111.0 (6)C5GA—C6GA—C8GA119.3 (8)
C8X—C7X—C12X115.0 (8)C3GA—C4GA—C5GA119.3 (8)
C8X—C7X—C1X121.2 (6)C2GA—C3GA—C4GA121.9 (8)
C12X—C7X—C1X123.8 (7)C4GA—C5GA—C6GA120.3 (9)
C11X—C10X—C9X121.2 (8)C3GB—C2GB—C1GB120.7 (8)
C11X—C10X—O1X123.2 (7)C3GB—C2GB—C7GB119.9 (9)
C9X—C10X—O1X115.6 (7)C1GB—C2GB—C7GB119.3 (9)
C17X—C16X—O2X118.4 (7)N1GB—C1GB—C6GB119.4 (7)
C17X—C16X—C15X119.9 (7)N1GB—C1GB—C2GB122.0 (8)
O2X—C16X—C15X121.7 (7)C6GB—C1GB—C2GB118.5 (8)
C16X—C17X—C18X120.4 (7)C4GB—C5GB—C6GB120.2 (8)
C9X—C8X—C7X123.2 (7)C1GB—C6GB—C5GB119.3 (8)
C1GC—C2GC—C3GC117.0 (7)C1GB—C6GB—C8GB120.9 (8)
C1GC—C2GC—C7GC122.1 (7)C5GB—C6GB—C8GB119.8 (8)
C3GC—C2GC—C7GC120.9 (8)C4GB—C3GB—C2GB121.3 (9)
C3X—C2X—C1X113.5 (6)C3GB—C4GB—C5GB120.0 (9)
C5X—C6X—C1X113.5 (6)C4Y—C3Y—C2Y112.5 (11)
C8X—C9X—C10X119.1 (7)C4Y—C5Y—C6Y113.2 (10)
C10X—C11X—C12X118.8 (7)C5Y—C4Y—C3Y110.1 (8)
C2GC—C1GC—C6GC121.8 (7)C2GD—C1GD—C6GD120.0
C2GC—C1GC—N1GC120.4 (7)C2GD—C1GD—N1GD120.3 (10)
C6GC—C1GC—N1GC117.8 (7)C6GD—C1GD—N1GD119.5 (10)
C13X—C18X—C17X121.0 (7)C3GD—C2GD—C1GD120.0
C14X—C13X—C18X118.1 (7)C3GD—C2GD—C7GD127.5 (11)
C14X—C13X—C1X120.7 (7)C1GD—C2GD—C7GD112.4 (11)
C18X—C13X—C1X121.0 (6)C2GD—C3GD—C4GD120.0
C7X—C12X—C11X122.7 (7)C5GD—C4GD—C3GD120.0
C3GC—C4GC—C5GC118.6 (8)C6GD—C5GD—C4GD120.0
C4GC—C3GC—C2GC122.8 (8)C8GD—C6GD—C5GD126.9 (11)
C1GC—C6GC—C5GC118.9 (8)C8GD—C6GD—C1GD113.1 (11)
C1GC—C6GC—C8GC121.5 (7)C5GD—C6GD—C1GD120.0
C5GC—C6GC—C8GC119.6 (7)C2GE—C1GE—C6GE120.0
C4GC—C5GC—C6GC120.9 (8)C2GE—C1GE—N1GE108.1 (13)
C3X—C4X—C5X110.3 (6)C6GE—C1GE—N1GE131.8 (13)
C6X—C5X—C4X110.7 (7)C7GE—C2GE—C1GE122.8 (14)
C16Y—C15Y—C14Y118.3 (8)C7GE—C2GE—C3GE117.0 (14)
C18Y—C17Y—C16Y121.0 (8)C1GE—C2GE—C3GE120.0
C13Y—C14Y—C15Y123.0 (8)C2GE—C3GE—C4GE120.0
C17Y—C18Y—C13Y123.4 (9)C5GE—C4GE—C3GE120.0
C15Y—C16Y—O2Y122.8 (8)C6GE—C5GE—C4GE120.0
C15Y—C16Y—C17Y118.7 (9)C8GE—C6GE—C5GE141.1 (14)
O2Y—C16Y—C17Y118.5 (8)C8GE—C6GE—C1GE98.9 (14)
C7Y—C1Y—C13Y104.0 (7)C5GE—C6GE—C1GE120.0
C7Y—C1Y—C2Y110.7 (8)C8Y—C7Y—C12Y120.0
C13Y—C1Y—C2Y112.4 (9)C8Y—C7Y—C1Y121.6 (5)
C7Y—C1Y—C6Y115.9 (9)C12Y—C7Y—C1Y118.3 (5)
C13Y—C1Y—C6Y110.6 (9)C9Y—C8Y—C7Y120.0
C2Y—C1Y—C6Y103.4 (8)C8Y—C9Y—C10Y120.0
C14Y—C13Y—C18Y115.5 (9)O1Y—C10Y—C9Y119.8
C14Y—C13Y—C1Y121.9 (8)O1Y—C10Y—C11Y120.2
C18Y—C13Y—C1Y122.2 (9)C9Y—C10Y—C11Y120.0
C3Y—C2Y—C1Y113.2 (8)C12Y—C11Y—C10Y120.0
C5Y—C6Y—C1Y114.1 (10)C11Y—C12Y—C7Y120.0
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2X—H2X···N1GC0.98 (3)1.85 (6)2.783 (8)159 (12)
O1X—H1X···O2Xi0.97 (3)1.92 (6)2.752 (7)142 (7)
O2Y—H2Y···N1GAii0.97 (3)2.01 (13)2.837 (10)141 (16)
Symmetry codes: (i) x, y+2, z+1; (ii) x+1, y, z.
(dc26x3) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 2,6-xylidine top
Crystal data top
C18H20O2/3(C8H11N)F(000) = 2736
Mr = 631.87Dx = 1.138 Mg m3
Dm = N/A Mg m3
Dm measured by not measured
Monoclinic, P21/nMelting point: 361.15K for guest release onset temp. and 463.15K fro host melting K
a = 9.807 (1) ÅMo Kα radiation, λ = 0.71069 Å
b = 25.464 (2) ŵ = 0.07 mm1
c = 29.842 (3) ÅT = 173 K
β = 98.28 (1)°Prism, colourless
V = 7374.6 (12) Å30.80 × 0.50 × 0.20 mm
Z = 8
Data collection top
Nonius Kappa CCD
diffractometer
8177 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.070
Graphite monochromatorθmax = 25.7°, θmin = 2.1°
0.8° φ scans and ω scansh = 011
13682 measured reflectionsk = 030
13682 independent reflectionsl = 3635
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.086H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.234 w = 1/[σ2(Fo2) + (0.0896P)2 + 7.8821P]
where P = (Fo2 + 2Fc2)/3
S = 1.06(Δ/σ)max = 0.023
13682 reflectionsΔρmax = 0.63 e Å3
923 parametersΔρmin = 0.25 e Å3
24 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0003 (5)
Special details top

Experimental. Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 50 mm; combination of φ and ω scans of 0.8°, 120 s per °, 2 iterations.

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*/Ueq
O1X0.0281 (2)0.56325 (9)0.02685 (9)0.0475 (6)
O1Y0.2937 (3)1.41895 (10)0.22382 (10)0.0560 (7)
H1Y0.209 (3)1.4315 (15)0.2389 (13)0.076 (14)*
O2X0.0233 (3)0.91931 (10)0.00057 (10)0.0556 (7)
H2X0.056 (4)0.9389 (18)0.0028 (18)0.12 (2)*
C8X0.1682 (3)0.67842 (13)0.08885 (12)0.0411 (8)
H8X0.25610.69430.09660.049*
C7X0.0543 (3)0.70114 (12)0.10456 (10)0.0310 (7)
C1Y0.3274 (3)1.23842 (14)0.10794 (11)0.0378 (8)
O2Y0.2805 (3)1.04680 (10)0.20892 (10)0.0614 (8)
H2Y0.187 (3)1.0354 (17)0.2147 (15)0.092 (16)*
C9X0.1573 (3)0.63385 (13)0.06251 (12)0.0438 (9)
H9X0.23700.62000.05200.053*
C11Y0.1820 (3)1.35598 (14)0.18136 (11)0.0407 (8)
H11Y0.09561.37280.18960.049*
C12X0.0711 (3)0.67566 (12)0.09183 (11)0.0356 (8)
H12X0.15170.68990.10140.043*
C12Y0.1925 (3)1.31247 (14)0.15321 (11)0.0396 (8)
H12Y0.11171.29980.14270.048*
C14X0.0749 (3)0.82181 (13)0.08135 (11)0.0374 (8)
H14X0.15440.81070.09360.045*
C7Y0.3167 (3)1.28669 (13)0.13978 (12)0.0388 (8)
C1X0.0645 (3)0.75286 (12)0.13139 (11)0.0331 (7)
C1GD0.1478 (3)0.74035 (16)0.07207 (13)0.0477 (9)
C10Y0.2977 (4)1.37471 (14)0.19727 (12)0.0445 (9)
C1GB0.5921 (3)0.74171 (16)0.19360 (12)0.0450 (9)
C13X0.0501 (3)0.79709 (12)0.09606 (11)0.0346 (8)
C2X0.0492 (3)0.75683 (13)0.16236 (11)0.0373 (8)
H2X10.04730.79250.17560.045*
H2X20.14020.75190.14370.045*
C16Y0.2858 (3)1.09364 (14)0.18613 (12)0.0442 (9)
N1GE0.2148 (3)0.98307 (13)0.01891 (13)0.0549 (9)
C18Y0.1919 (3)1.15828 (16)0.14128 (13)0.0539 (10)
H18Y0.11641.17000.12720.065*
C2Y0.2170 (3)1.24064 (15)0.07528 (12)0.0438 (9)
H2Y10.12511.24460.09370.053*
H2Y20.21761.20660.05920.053*
C15Y0.4024 (4)1.12448 (15)0.18429 (14)0.0530 (10)
H15Y0.47541.11370.20000.064*
C16X0.0259 (4)0.87859 (13)0.03076 (13)0.0442 (9)
C11X0.0829 (3)0.63017 (12)0.06564 (11)0.0362 (8)
H11X0.17010.61380.05780.043*
C18X0.1611 (4)0.81338 (15)0.07485 (13)0.0495 (9)
H18X0.24770.79660.08260.059*
C10X0.0323 (3)0.60907 (12)0.05116 (11)0.0347 (7)
C6X0.2044 (3)0.75738 (14)0.16318 (12)0.0434 (9)
H6X10.28030.75270.14500.052*
H6X20.21260.79310.17640.052*
C13Y0.3103 (3)1.18901 (13)0.13689 (11)0.0373 (8)
C15X0.0885 (3)0.86209 (13)0.04951 (12)0.0432 (9)
H15X0.17560.87820.04060.052*
C8Y0.4301 (4)1.30601 (15)0.15742 (15)0.0562 (11)
H8Y0.51671.28920.14960.067*
C6GB0.5836 (4)0.78593 (16)0.16577 (14)0.0522 (10)
C6Y0.4686 (3)1.23552 (16)0.07623 (13)0.0506 (10)
H6Y10.47511.20140.06020.061*
H6Y20.54391.23700.09500.061*
C5Y0.4889 (4)1.27890 (17)0.04179 (14)0.0581 (11)
H5Y10.48961.31310.05760.070*
H5Y20.57931.27450.02260.070*
C5GD0.1703 (4)0.7774 (2)0.14687 (15)0.0619 (12)
H5GD0.17490.80720.16620.074*
C5X0.2208 (3)0.71745 (16)0.20135 (12)0.0487 (9)
H5X10.31060.72300.22060.058*
H5X20.22110.68170.18840.058*
C5GB0.5717 (4)0.77942 (19)0.12005 (15)0.0585 (11)
H5GB0.56560.80950.10100.070*
C6GD0.1541 (3)0.78486 (16)0.10023 (15)0.0529 (10)
C3GD0.1746 (3)0.68518 (17)0.13774 (13)0.0541 (10)
H3GD0.18170.65100.15060.065*
C9Y0.4213 (4)1.34871 (16)0.18591 (15)0.0603 (11)
H9Y0.50071.36040.19780.072*
C4GD0.1799 (4)0.72778 (19)0.16581 (14)0.0587 (11)
H4GD0.19000.72340.19770.070*
C3X0.0334 (3)0.71665 (15)0.20069 (11)0.0434 (9)
H3X10.10770.72190.21950.052*
H3X20.04310.68080.18770.052*
C4Y0.3757 (4)1.27909 (18)0.01202 (13)0.0594 (11)
H4Y10.38891.30920.00920.071*
H4Y20.38031.24640.00610.071*
N1GD0.1342 (4)0.74661 (18)0.02525 (13)0.0626 (10)
C14Y0.4144 (3)1.17079 (15)0.16000 (13)0.0479 (9)
H14Y0.49641.19090.15900.058*
C3Y0.2354 (4)1.28322 (16)0.04122 (13)0.0544 (10)
H3Y10.16191.28100.02180.065*
H3Y20.22731.31770.05680.065*
C2GD0.1593 (3)0.69031 (15)0.09099 (12)0.0458 (9)
C17Y0.1787 (4)1.11145 (16)0.16512 (14)0.0560 (11)
H17Y0.09591.09170.16700.067*
C4GB0.5685 (4)0.7304 (2)0.10111 (14)0.0621 (12)
H4GB0.56130.72650.06920.075*
C17X0.1491 (4)0.85272 (15)0.04323 (14)0.0527 (10)
H17X0.22730.86240.02960.063*
N1GB0.6017 (4)0.7471 (2)0.24048 (14)0.0783 (13)
C4X0.1058 (4)0.72158 (17)0.23033 (12)0.0537 (10)
H4X10.11160.75580.24620.064*
H4X20.11600.69340.25340.064*
C3GB0.5757 (4)0.68665 (19)0.12869 (17)0.0631 (12)
H3GB0.57290.65260.11550.076*
C2GE0.4271 (4)0.93247 (15)0.01796 (14)0.0514 (10)
C7GD0.1558 (4)0.64279 (17)0.06120 (15)0.0660 (12)
H7D10.06640.64080.04180.099*
H7D20.16950.61120.08000.099*
H7D30.22930.64530.04230.099*
C1GE0.3183 (4)0.96374 (14)0.00453 (15)0.0520 (10)
C2GB0.5870 (3)0.69165 (16)0.17485 (14)0.0517 (10)
C7GE0.4449 (4)0.92519 (17)0.06814 (15)0.0645 (11)
H7E10.45670.95950.08300.097*
H7E20.52640.90350.07770.097*
H7E30.36310.90780.07660.097*
C7GB0.5925 (5)0.6435 (2)0.2042 (2)0.0956 (18)
H7B10.58680.61200.18510.143*
H7B20.51500.64390.22160.143*
H7B30.67940.64310.22510.143*
C4GE0.5036 (4)0.91838 (17)0.05397 (17)0.0657 (12)
H4GE0.56760.90250.07090.079*
C6GE0.3043 (4)0.97321 (15)0.05007 (14)0.0516 (10)
C8GB0.5866 (6)0.8404 (2)0.1862 (2)0.1025 (19)
H8B10.57350.86660.16190.154*
H8B20.67570.84620.20500.154*
H8B30.51260.84370.20480.154*
C8GD0.1387 (5)0.83846 (19)0.07990 (18)0.0830 (15)
H8D10.04820.84150.06130.125*
H8D20.21100.84420.06090.125*
H8D30.14700.86480.10410.125*
C3GE0.5165 (4)0.91023 (16)0.00758 (16)0.0617 (11)
H3GE0.58910.88870.00670.074*
C5GE0.3997 (5)0.94895 (17)0.07568 (16)0.0656 (12)
H5GE0.39100.95400.10750.079*
C8GE0.1918 (5)1.00692 (19)0.07502 (15)0.0750 (13)
H8E10.10180.99280.07050.112*
H8E20.19941.00700.10740.112*
H8E30.20101.04290.06330.112*
N1GA0.7727 (3)0.51557 (12)0.00316 (10)0.0408 (7)
C1GC1.0442 (3)0.48023 (13)0.21449 (11)0.0386 (8)
N1GC0.9616 (3)0.46946 (12)0.24895 (11)0.0441 (7)
C6GA0.5826 (3)0.54499 (14)0.04114 (12)0.0426 (8)
C5GA0.5130 (4)0.54082 (17)0.07846 (14)0.0558 (10)
H5GA0.43650.56320.08040.067*
C2GA0.7376 (4)0.47594 (15)0.07425 (12)0.0465 (9)
C6GC1.0046 (4)0.52186 (15)0.18453 (12)0.0488 (9)
C7GA0.8600 (4)0.44051 (16)0.07279 (14)0.0580 (10)
H7A10.84290.41780.04610.087*
H7A20.87450.41880.10020.087*
H7A30.94220.46190.07110.087*
C1GA0.6956 (3)0.51141 (13)0.03946 (11)0.0386 (8)
C8GA0.5387 (4)0.58380 (15)0.00438 (14)0.0563 (10)
H8A10.61000.61080.00440.085*
H8A20.45210.60030.00960.085*
H8A30.52510.56580.02490.085*
C2GC1.1572 (3)0.44827 (14)0.21009 (12)0.0423 (8)
C7GC1.1968 (4)0.40357 (14)0.24161 (13)0.0504 (9)
H7C11.21060.41640.27290.076*
H7C21.28250.38780.23470.076*
H7C31.12340.37710.23800.076*
C3GC1.2317 (4)0.45967 (18)0.17476 (14)0.0590 (11)
H3GC1.30880.43850.17090.071*
C8GC0.8829 (4)0.55609 (16)0.18897 (14)0.0612 (11)
H8C10.80200.53400.19090.092*
H8C20.86450.57910.16250.092*
H8C30.90260.57750.21650.092*
C3GA0.6640 (4)0.47347 (18)0.11052 (13)0.0606 (11)
H3GA0.69130.44930.13440.073*
C5GC1.0836 (4)0.5315 (2)0.15028 (14)0.0681 (13)
H5GC1.05940.55970.12990.082*
C4GA0.5515 (4)0.50554 (19)0.11245 (14)0.0660 (12)
H4GA0.50110.50310.13730.079*
C4GC1.1962 (4)0.5010 (2)0.14531 (15)0.0713 (13)
H4GC1.24920.50820.12180.086*
N1GF0.9800 (3)0.00363 (13)0.23781 (11)0.0450 (7)
C1GF1.0683 (3)0.00496 (14)0.20486 (11)0.0412 (8)
C5GF1.2618 (4)0.01866 (17)0.16874 (14)0.0566 (10)
H5GF1.33730.04120.16590.068*
C2GF1.0400 (4)0.04724 (15)0.17449 (12)0.0481 (9)
C6GF1.1783 (4)0.02941 (14)0.20180 (13)0.0462 (9)
C7GF0.9195 (4)0.08264 (16)0.17746 (14)0.0624 (11)
H7F10.90770.10670.15150.094*
H7F30.83590.06140.17720.094*
H7F20.93600.10290.20560.094*
C8GF1.2058 (4)0.07512 (15)0.23326 (15)0.0602 (11)
H8F11.12400.09760.23070.090*
H8F21.28390.09530.22530.090*
H8F31.22770.06240.26440.090*
C3GF1.1273 (4)0.05620 (17)0.14266 (13)0.0578 (11)
H3GF1.11060.08500.12240.069*
C4GF1.2376 (4)0.02376 (18)0.14018 (13)0.0622 (11)
H4GF1.29770.03060.11860.075*
H1D10.106 (5)0.7176 (16)0.0044 (14)0.089 (16)*
H1D20.096 (4)0.7776 (14)0.0139 (15)0.080 (16)*
H1B10.634 (6)0.7780 (17)0.2551 (19)0.13 (2)*
H1B20.630 (6)0.7139 (18)0.255 (2)0.14 (3)*
H1C11.020 (3)0.4542 (14)0.2729 (11)0.057 (12)*
H1A10.720 (4)0.5286 (15)0.0230 (11)0.061 (12)*
H1F11.017 (3)0.0245 (13)0.2602 (11)0.048 (11)*
H1E10.251 (5)0.982 (2)0.0507 (12)0.11 (2)*
H1F20.935 (3)0.0259 (12)0.2465 (12)0.052 (11)*
H1A20.818 (4)0.4860 (13)0.0055 (13)0.070 (13)*
H1E20.178 (3)1.0154 (12)0.0080 (12)0.058 (12)*
H1C20.924 (3)0.5015 (12)0.2616 (11)0.056 (11)*
H1X0.061 (3)0.5490 (14)0.0180 (13)0.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1X0.0444 (14)0.0424 (14)0.0591 (16)0.0015 (11)0.0196 (12)0.0149 (12)
O1Y0.0511 (17)0.0485 (16)0.0722 (19)0.0006 (13)0.0219 (14)0.0092 (14)
O2X0.0488 (16)0.0427 (15)0.0776 (19)0.0036 (13)0.0173 (14)0.0177 (14)
C8X0.0239 (17)0.042 (2)0.059 (2)0.0020 (14)0.0135 (15)0.0035 (17)
C7X0.0232 (16)0.0328 (17)0.0378 (18)0.0000 (13)0.0067 (13)0.0022 (14)
C1Y0.0218 (16)0.050 (2)0.0419 (19)0.0004 (14)0.0057 (14)0.0042 (16)
O2Y0.0466 (16)0.0492 (16)0.093 (2)0.0029 (13)0.0235 (15)0.0253 (15)
C9X0.0322 (18)0.043 (2)0.060 (2)0.0038 (15)0.0217 (17)0.0071 (18)
C11Y0.0251 (17)0.051 (2)0.047 (2)0.0029 (15)0.0086 (15)0.0054 (17)
C12X0.0229 (16)0.0357 (18)0.048 (2)0.0039 (14)0.0054 (14)0.0022 (15)
C12Y0.0245 (17)0.052 (2)0.043 (2)0.0034 (15)0.0079 (14)0.0037 (17)
C14X0.0262 (17)0.0382 (19)0.049 (2)0.0043 (14)0.0083 (15)0.0020 (16)
C7Y0.0224 (16)0.044 (2)0.051 (2)0.0033 (14)0.0109 (15)0.0148 (17)
C1X0.0208 (15)0.0354 (18)0.0433 (19)0.0002 (13)0.0050 (14)0.0063 (14)
C1GD0.0227 (17)0.068 (3)0.052 (2)0.0075 (17)0.0068 (16)0.006 (2)
C10Y0.044 (2)0.036 (2)0.055 (2)0.0049 (16)0.0152 (17)0.0033 (17)
C1GB0.0246 (17)0.068 (3)0.043 (2)0.0036 (16)0.0064 (15)0.0057 (19)
C13X0.0266 (17)0.0280 (17)0.051 (2)0.0012 (13)0.0101 (15)0.0015 (15)
C2X0.0284 (17)0.0397 (19)0.044 (2)0.0004 (14)0.0046 (15)0.0061 (15)
C16Y0.0363 (19)0.042 (2)0.056 (2)0.0021 (16)0.0123 (17)0.0053 (17)
N1GE0.0448 (19)0.044 (2)0.076 (3)0.0037 (16)0.0086 (18)0.0119 (18)
C18Y0.0296 (19)0.067 (3)0.068 (3)0.0007 (18)0.0157 (18)0.021 (2)
C2Y0.0272 (17)0.060 (2)0.045 (2)0.0021 (16)0.0058 (15)0.0095 (18)
C15Y0.036 (2)0.054 (2)0.074 (3)0.0012 (17)0.0253 (19)0.014 (2)
C16X0.041 (2)0.0342 (19)0.059 (2)0.0056 (16)0.0131 (17)0.0047 (17)
C11X0.0298 (17)0.0364 (19)0.0424 (19)0.0019 (14)0.0048 (15)0.0041 (15)
C18X0.0327 (19)0.050 (2)0.068 (3)0.0032 (16)0.0163 (18)0.008 (2)
C10X0.0338 (18)0.0319 (18)0.0399 (19)0.0021 (14)0.0104 (15)0.0032 (15)
C6X0.0265 (17)0.051 (2)0.051 (2)0.0060 (15)0.0015 (15)0.0096 (18)
C13Y0.0252 (17)0.046 (2)0.0417 (19)0.0024 (14)0.0068 (14)0.0021 (16)
C15X0.0293 (18)0.0374 (19)0.064 (2)0.0027 (15)0.0094 (16)0.0058 (17)
C8Y0.0291 (19)0.048 (2)0.096 (3)0.0040 (16)0.022 (2)0.009 (2)
C6GB0.033 (2)0.059 (3)0.066 (3)0.0031 (17)0.0154 (18)0.007 (2)
C6Y0.0299 (19)0.060 (2)0.061 (2)0.0030 (17)0.0031 (17)0.015 (2)
C5Y0.042 (2)0.065 (3)0.065 (3)0.0023 (19)0.0002 (19)0.003 (2)
C5GD0.032 (2)0.084 (3)0.070 (3)0.012 (2)0.0047 (19)0.030 (3)
C5X0.0327 (19)0.066 (3)0.046 (2)0.0009 (17)0.0005 (16)0.0027 (19)
C5GB0.030 (2)0.080 (3)0.067 (3)0.0038 (19)0.0107 (19)0.018 (2)
C6GD0.0273 (19)0.057 (3)0.075 (3)0.0065 (17)0.0094 (18)0.004 (2)
C3GD0.031 (2)0.075 (3)0.057 (3)0.0016 (18)0.0067 (17)0.001 (2)
C9Y0.036 (2)0.054 (2)0.097 (3)0.0018 (18)0.032 (2)0.009 (2)
C4GD0.036 (2)0.086 (3)0.052 (2)0.001 (2)0.0003 (18)0.012 (2)
C3X0.0357 (19)0.054 (2)0.041 (2)0.0002 (16)0.0080 (15)0.0024 (17)
C4Y0.056 (2)0.073 (3)0.048 (2)0.007 (2)0.0044 (19)0.006 (2)
N1GD0.053 (2)0.080 (3)0.056 (2)0.004 (2)0.0131 (18)0.006 (2)
C14Y0.0291 (18)0.054 (2)0.064 (2)0.0043 (16)0.0174 (17)0.0080 (19)
C3Y0.045 (2)0.066 (3)0.053 (2)0.0039 (19)0.0086 (18)0.005 (2)
C2GD0.0244 (17)0.063 (3)0.051 (2)0.0042 (16)0.0070 (15)0.0042 (19)
C17Y0.034 (2)0.059 (3)0.077 (3)0.0092 (18)0.0182 (19)0.020 (2)
C4GB0.032 (2)0.110 (4)0.044 (2)0.001 (2)0.0025 (17)0.009 (3)
C17X0.035 (2)0.054 (2)0.074 (3)0.0003 (17)0.0254 (19)0.012 (2)
N1GB0.059 (2)0.127 (4)0.051 (2)0.013 (3)0.0157 (19)0.016 (3)
C4X0.043 (2)0.072 (3)0.044 (2)0.0024 (19)0.0006 (17)0.000 (2)
C3GB0.034 (2)0.068 (3)0.088 (3)0.0001 (19)0.011 (2)0.024 (3)
C2GE0.040 (2)0.044 (2)0.072 (3)0.0080 (17)0.0128 (19)0.007 (2)
C7GD0.063 (3)0.070 (3)0.068 (3)0.010 (2)0.018 (2)0.012 (2)
C1GE0.046 (2)0.040 (2)0.071 (3)0.0074 (17)0.014 (2)0.0125 (19)
C2GB0.0300 (19)0.060 (3)0.065 (3)0.0013 (17)0.0047 (18)0.001 (2)
C7GE0.059 (3)0.061 (3)0.076 (3)0.002 (2)0.017 (2)0.001 (2)
C7GB0.073 (3)0.082 (4)0.137 (5)0.014 (3)0.033 (3)0.045 (3)
C4GE0.048 (2)0.063 (3)0.092 (4)0.006 (2)0.029 (2)0.019 (3)
C6GE0.046 (2)0.044 (2)0.067 (3)0.0078 (18)0.014 (2)0.011 (2)
C8GB0.102 (4)0.068 (3)0.147 (5)0.015 (3)0.051 (4)0.031 (4)
C8GD0.070 (3)0.070 (3)0.114 (4)0.013 (3)0.029 (3)0.000 (3)
C3GE0.055 (3)0.057 (3)0.076 (3)0.000 (2)0.019 (2)0.008 (2)
C5GE0.066 (3)0.060 (3)0.074 (3)0.018 (2)0.019 (2)0.013 (2)
C8GE0.084 (3)0.076 (3)0.064 (3)0.008 (3)0.007 (2)0.010 (2)
N1GA0.0419 (17)0.0406 (18)0.0410 (18)0.0006 (14)0.0095 (14)0.0031 (14)
C1GC0.0369 (19)0.044 (2)0.0351 (18)0.0063 (15)0.0064 (15)0.0005 (15)
N1GC0.0445 (18)0.0435 (18)0.0469 (18)0.0047 (14)0.0154 (15)0.0022 (15)
C6GA0.0326 (19)0.042 (2)0.053 (2)0.0032 (15)0.0059 (16)0.0032 (17)
C5GA0.034 (2)0.067 (3)0.068 (3)0.0000 (18)0.0145 (19)0.010 (2)
C2GA0.039 (2)0.055 (2)0.045 (2)0.0020 (17)0.0058 (16)0.0007 (18)
C6GC0.044 (2)0.057 (2)0.044 (2)0.0082 (18)0.0016 (17)0.0041 (18)
C7GA0.055 (2)0.056 (2)0.063 (3)0.011 (2)0.012 (2)0.010 (2)
C1GA0.0331 (18)0.0385 (19)0.045 (2)0.0064 (15)0.0082 (15)0.0066 (16)
C8GA0.041 (2)0.043 (2)0.085 (3)0.0025 (17)0.010 (2)0.001 (2)
C2GC0.0353 (19)0.049 (2)0.043 (2)0.0078 (16)0.0056 (16)0.0047 (17)
C7GC0.043 (2)0.050 (2)0.059 (2)0.0001 (17)0.0099 (18)0.0078 (19)
C3GC0.038 (2)0.084 (3)0.058 (3)0.003 (2)0.0154 (19)0.008 (2)
C8GC0.059 (3)0.059 (3)0.064 (3)0.008 (2)0.004 (2)0.011 (2)
C3GA0.052 (2)0.082 (3)0.050 (2)0.003 (2)0.0136 (19)0.011 (2)
C5GC0.051 (3)0.096 (4)0.057 (3)0.008 (2)0.007 (2)0.026 (2)
C4GA0.049 (2)0.097 (4)0.056 (3)0.002 (2)0.025 (2)0.004 (2)
C4GC0.052 (3)0.110 (4)0.055 (3)0.009 (3)0.014 (2)0.016 (3)
N1GF0.0438 (18)0.0416 (19)0.053 (2)0.0019 (15)0.0164 (15)0.0032 (16)
C1GF0.0376 (19)0.044 (2)0.043 (2)0.0054 (16)0.0095 (16)0.0047 (16)
C5GF0.050 (2)0.063 (3)0.060 (3)0.007 (2)0.018 (2)0.009 (2)
C2GF0.053 (2)0.049 (2)0.042 (2)0.0012 (18)0.0073 (18)0.0008 (17)
C6GF0.039 (2)0.046 (2)0.054 (2)0.0037 (16)0.0088 (17)0.0065 (18)
C7GF0.070 (3)0.053 (2)0.064 (3)0.011 (2)0.012 (2)0.011 (2)
C8GF0.049 (2)0.050 (2)0.083 (3)0.0005 (19)0.013 (2)0.002 (2)
C3GF0.069 (3)0.060 (3)0.046 (2)0.003 (2)0.014 (2)0.0026 (19)
C4GF0.069 (3)0.077 (3)0.044 (2)0.008 (2)0.022 (2)0.005 (2)
Geometric parameters (Å, º) top
O1X—C10X1.371 (4)C3Y—H3Y20.9900
O1X—H1X0.949 (19)C2GD—C7GD1.499 (5)
O1Y—C10Y1.375 (4)C17Y—H17Y0.9500
O1Y—H1Y0.94 (2)C4GB—C3GB1.381 (6)
O2X—C16X1.371 (4)C4GB—H4GB0.9500
O2X—H2X0.91 (2)C17X—H17X0.9500
C8X—C9X1.376 (5)N1GB—H1B10.93 (3)
C8X—C7X1.398 (4)N1GB—H1B20.97 (3)
C8X—H8X0.9500C4X—H4X10.9900
C7X—C12X1.394 (4)C4X—H4X20.9900
C7X—C1X1.537 (4)C3GB—C2GB1.372 (6)
C1Y—C13Y1.522 (5)C3GB—H3GB0.9500
C1Y—C7Y1.548 (5)C2GE—C3GE1.364 (5)
C1Y—C2Y1.558 (4)C2GE—C1GE1.421 (5)
C1Y—C6Y1.563 (5)C2GE—C7GE1.494 (6)
O2Y—C16Y1.370 (4)C7GD—H7D10.9800
O2Y—H2Y0.95 (2)C7GD—H7D20.9800
C9X—C10X1.378 (4)C7GD—H7D30.9800
C9X—H9X0.9500C1GE—C6GE1.368 (6)
C11Y—C10Y1.376 (5)C2GB—C7GB1.505 (6)
C11Y—C12Y1.385 (5)C7GE—H7E10.9800
C11Y—H11Y0.9500C7GE—H7E20.9800
C12X—C11X1.393 (4)C7GE—H7E30.9800
C12X—H12X0.9500C7GB—H7B10.9800
C12Y—C7Y1.391 (5)C7GB—H7B20.9800
C12Y—H12Y0.9500C7GB—H7B30.9800
C14X—C13X1.391 (4)C4GE—C5GE1.369 (6)
C14X—C15X1.391 (5)C4GE—C3GE1.388 (6)
C14X—H14X0.9500C4GE—H4GE0.9500
C7Y—C8Y1.387 (5)C6GE—C5GE1.431 (5)
C1X—C13X1.535 (4)C6GE—C8GE1.507 (6)
C1X—C2X1.550 (4)C8GB—H8B10.9800
C1X—C6X1.556 (4)C8GB—H8B20.9800
C1GD—C2GD1.392 (5)C8GB—H8B30.9800
C1GD—N1GD1.393 (5)C8GD—H8D10.9800
C1GD—C6GD1.407 (5)C8GD—H8D20.9800
C10Y—C9Y1.380 (5)C8GD—H8D30.9800
C1GB—C2GB1.390 (5)C3GE—H3GE0.9500
C1GB—C6GB1.394 (5)C5GE—H5GE0.9500
C1GB—N1GB1.395 (5)C8GE—H8E10.9800
C13X—C18X1.399 (4)C8GE—H8E20.9800
C2X—C3X1.526 (5)C8GE—H8E30.9800
C2X—H2X10.9900N1GA—C1GA1.411 (4)
C2X—H2X20.9900N1GA—H1A10.94 (3)
C16Y—C17Y1.376 (5)N1GA—H1A20.93 (2)
C16Y—C15Y1.382 (5)C1GC—C2GC1.396 (5)
N1GE—C1GE1.402 (5)C1GC—C6GC1.405 (5)
N1GE—H1E10.96 (3)C1GC—N1GC1.424 (4)
N1GE—H1E20.94 (2)N1GC—H1C10.93 (3)
C18Y—C17Y1.385 (5)N1GC—H1C20.993 (19)
C18Y—C13Y1.390 (5)C6GA—C5GA1.391 (5)
C18Y—H18Y0.9500C6GA—C1GA1.406 (5)
C2Y—C3Y1.479 (5)C6GA—C8GA1.493 (5)
C2Y—H2Y10.9900C5GA—C4GA1.367 (6)
C2Y—H2Y20.9900C5GA—H5GA0.9500
C15Y—C14Y1.380 (5)C2GA—C3GA1.386 (5)
C15Y—H15Y0.9500C2GA—C1GA1.393 (5)
C16X—C17X1.379 (5)C2GA—C7GA1.508 (5)
C16X—C15X1.390 (5)C6GC—C5GC1.391 (5)
C11X—C10X1.375 (4)C6GC—C8GC1.499 (5)
C11X—H11X0.9500C7GA—H7A10.9800
C18X—C17X1.370 (5)C7GA—H7A20.9800
C18X—H18X0.9500C7GA—H7A30.9800
C6X—C5X1.518 (5)C8GA—H8A10.9800
C6X—H6X10.9900C8GA—H8A20.9800
C6X—H6X20.9900C8GA—H8A30.9800
C13Y—C14Y1.391 (4)C2GC—C3GC1.397 (5)
C15X—H15X0.9500C2GC—C7GC1.492 (5)
C8Y—C9Y1.375 (5)C7GC—H7C10.9800
C8Y—H8Y0.9500C7GC—H7C20.9800
C6GB—C5GB1.363 (6)C7GC—H7C30.9800
C6GB—C8GB1.513 (6)C3GC—C4GC1.383 (6)
C6Y—C5Y1.502 (5)C3GC—H3GC0.9500
C6Y—H6Y10.9900C8GC—H8C10.9800
C6Y—H6Y20.9900C8GC—H8C20.9800
C5Y—C4Y1.518 (5)C8GC—H8C30.9800
C5Y—H5Y10.9900C3GA—C4GA1.380 (6)
C5Y—H5Y20.9900C3GA—H3GA0.9500
C5GD—C4GD1.382 (6)C5GC—C4GC1.375 (6)
C5GD—C6GD1.391 (6)C5GC—H5GC0.9500
C5GD—H5GD0.9500C4GA—H4GA0.9500
C5X—C4X1.521 (5)C4GC—H4GC0.9500
C5X—H5X10.9900N1GF—C1GF1.418 (4)
C5X—H5X20.9900N1GF—H1F10.89 (3)
C5GB—C4GB1.369 (6)N1GF—H1F20.93 (2)
C5GB—H5GB0.9500C1GF—C6GF1.402 (5)
C6GD—C8GD1.492 (6)C1GF—C2GF1.409 (5)
C3GD—C4GD1.367 (6)C5GF—C4GF1.375 (6)
C3GD—C2GD1.388 (5)C5GF—C6GF1.397 (5)
C3GD—H3GD0.9500C5GF—H5GF0.9500
C9Y—H9Y0.9500C2GF—C3GF1.386 (5)
C4GD—H4GD0.9500C2GF—C7GF1.500 (5)
C3X—C4X1.521 (5)C6GF—C8GF1.495 (5)
C3X—H3X10.9900C7GF—H7F10.9800
C3X—H3X20.9900C7GF—H7F30.9800
C4Y—C3Y1.523 (5)C7GF—H7F20.9800
C4Y—H4Y10.9900C8GF—H8F10.9800
C4Y—H4Y20.9900C8GF—H8F20.9800
N1GD—H1D10.98 (3)C8GF—H8F30.9800
N1GD—H1D20.92 (3)C3GF—C4GF1.372 (6)
C14Y—H14Y0.9500C3GF—H3GF0.9500
C3Y—H3Y10.9900C4GF—H4GF0.9500
C10X—O1X—H1X115 (2)C5GB—C4GB—H4GB120.2
C10Y—O1Y—H1Y120 (3)C3GB—C4GB—H4GB120.2
C16X—O2X—H2X115 (3)C18X—C17X—C16X121.3 (3)
C9X—C8X—C7X122.2 (3)C18X—C17X—H17X119.3
C9X—C8X—H8X118.9C16X—C17X—H17X119.3
C7X—C8X—H8X118.9C1GB—N1GB—H1B1121 (4)
C12X—C7X—C8X115.6 (3)C1GB—N1GB—H1B2109 (4)
C12X—C7X—C1X121.9 (3)H1B1—N1GB—H1B2118 (6)
C8X—C7X—C1X122.3 (3)C5X—C4X—C3X109.9 (3)
C13Y—C1Y—C7Y108.4 (3)C5X—C4X—H4X1109.7
C13Y—C1Y—C2Y110.8 (3)C3X—C4X—H4X1109.7
C7Y—C1Y—C2Y111.3 (3)C5X—C4X—H4X2109.7
C13Y—C1Y—C6Y108.7 (3)C3X—C4X—H4X2109.7
C7Y—C1Y—C6Y112.6 (3)H4X1—C4X—H4X2108.2
C2Y—C1Y—C6Y104.9 (3)C2GB—C3GB—C4GB120.9 (4)
C16Y—O2Y—H2Y109 (3)C2GB—C3GB—H3GB119.6
C8X—C9X—C10X120.8 (3)C4GB—C3GB—H3GB119.6
C8X—C9X—H9X119.6C3GE—C2GE—C1GE117.9 (4)
C10X—C9X—H9X119.6C3GE—C2GE—C7GE121.1 (4)
C10Y—C11Y—C12Y119.6 (3)C1GE—C2GE—C7GE120.9 (4)
C10Y—C11Y—H11Y120.2C2GD—C7GD—H7D1109.5
C12Y—C11Y—H11Y120.2C2GD—C7GD—H7D2109.5
C11X—C12X—C7X122.6 (3)H7D1—C7GD—H7D2109.5
C11X—C12X—H12X118.7C2GD—C7GD—H7D3109.5
C7X—C12X—H12X118.7H7D1—C7GD—H7D3109.5
C11Y—C12Y—C7Y122.5 (3)H7D2—C7GD—H7D3109.5
C11Y—C12Y—H12Y118.7C6GE—C1GE—N1GE117.2 (4)
C7Y—C12Y—H12Y118.7C6GE—C1GE—C2GE121.9 (4)
C13X—C14X—C15X122.9 (3)N1GE—C1GE—C2GE120.7 (4)
C13X—C14X—H14X118.6C3GB—C2GB—C1GB118.8 (4)
C15X—C14X—H14X118.6C3GB—C2GB—C7GB120.0 (4)
C8Y—C7Y—C12Y116.1 (3)C1GB—C2GB—C7GB121.1 (4)
C8Y—C7Y—C1Y121.8 (3)C2GE—C7GE—H7E1109.5
C12Y—C7Y—C1Y122.0 (3)C2GE—C7GE—H7E2109.5
C13X—C1X—C7X106.1 (3)H7E1—C7GE—H7E2109.5
C13X—C1X—C2X111.0 (2)C2GE—C7GE—H7E3109.5
C7X—C1X—C2X111.6 (2)H7E1—C7GE—H7E3109.5
C13X—C1X—C6X110.5 (3)H7E2—C7GE—H7E3109.5
C7X—C1X—C6X111.5 (3)C2GB—C7GB—H7B1109.5
C2X—C1X—C6X106.2 (3)C2GB—C7GB—H7B2109.5
C2GD—C1GD—N1GD120.1 (4)H7B1—C7GB—H7B2109.5
C2GD—C1GD—C6GD120.1 (4)C2GB—C7GB—H7B3109.5
N1GD—C1GD—C6GD119.8 (4)H7B1—C7GB—H7B3109.5
O1Y—C10Y—C11Y121.8 (3)H7B2—C7GB—H7B3109.5
O1Y—C10Y—C9Y119.0 (3)C5GE—C4GE—C3GE120.8 (4)
C11Y—C10Y—C9Y119.2 (3)C5GE—C4GE—H4GE119.6
C2GB—C1GB—C6GB120.3 (4)C3GE—C4GE—H4GE119.6
C2GB—C1GB—N1GB119.2 (4)C1GE—C6GE—C5GE118.4 (4)
C6GB—C1GB—N1GB120.5 (4)C1GE—C6GE—C8GE123.5 (4)
C14X—C13X—C18X115.5 (3)C5GE—C6GE—C8GE118.1 (4)
C14X—C13X—C1X122.6 (3)C6GB—C8GB—H8B1109.5
C18X—C13X—C1X121.9 (3)C6GB—C8GB—H8B2109.5
C3X—C2X—C1X113.5 (3)H8B1—C8GB—H8B2109.5
C3X—C2X—H2X1108.9C6GB—C8GB—H8B3109.5
C1X—C2X—H2X1108.9H8B1—C8GB—H8B3109.5
C3X—C2X—H2X2108.9H8B2—C8GB—H8B3109.5
C1X—C2X—H2X2108.9C6GD—C8GD—H8D1109.5
H2X1—C2X—H2X2107.7C6GD—C8GD—H8D2109.5
O2Y—C16Y—C17Y122.4 (3)H8D1—C8GD—H8D2109.5
O2Y—C16Y—C15Y119.1 (3)C6GD—C8GD—H8D3109.5
C17Y—C16Y—C15Y118.5 (3)H8D1—C8GD—H8D3109.5
C1GE—N1GE—H1E1107 (3)H8D2—C8GD—H8D3109.5
C1GE—N1GE—H1E2114 (2)C2GE—C3GE—C4GE121.5 (4)
H1E1—N1GE—H1E2116 (4)C2GE—C3GE—H3GE119.3
C17Y—C18Y—C13Y123.2 (3)C4GE—C3GE—H3GE119.3
C17Y—C18Y—H18Y118.4C4GE—C5GE—C6GE119.5 (4)
C13Y—C18Y—H18Y118.4C4GE—C5GE—H5GE120.3
C3Y—C2Y—C1Y115.4 (3)C6GE—C5GE—H5GE120.3
C3Y—C2Y—H2Y1108.4C6GE—C8GE—H8E1109.5
C1Y—C2Y—H2Y1108.4C6GE—C8GE—H8E2109.5
C3Y—C2Y—H2Y2108.4H8E1—C8GE—H8E2109.5
C1Y—C2Y—H2Y2108.4C6GE—C8GE—H8E3109.5
H2Y1—C2Y—H2Y2107.5H8E1—C8GE—H8E3109.5
C14Y—C15Y—C16Y120.9 (3)H8E2—C8GE—H8E3109.5
C14Y—C15Y—H15Y119.6C1GA—N1GA—H1A1112 (2)
C16Y—C15Y—H15Y119.6C1GA—N1GA—H1A2119 (3)
O2X—C16X—C17X118.1 (3)H1A1—N1GA—H1A2107 (3)
O2X—C16X—C15X123.6 (3)C2GC—C1GC—C6GC122.0 (3)
C17X—C16X—C15X118.3 (3)C2GC—C1GC—N1GC119.8 (3)
C10X—C11X—C12X119.7 (3)C6GC—C1GC—N1GC118.1 (3)
C10X—C11X—H11X120.1C1GC—N1GC—H1C1107 (2)
C12X—C11X—H11X120.1C1GC—N1GC—H1C2114 (2)
C17X—C18X—C13X122.3 (3)H1C1—N1GC—H1C2106 (3)
C17X—C18X—H18X118.9C5GA—C6GA—C1GA117.5 (3)
C13X—C18X—H18X118.9C5GA—C6GA—C8GA121.0 (3)
O1X—C10X—C11X122.4 (3)C1GA—C6GA—C8GA121.4 (3)
O1X—C10X—C9X118.5 (3)C4GA—C5GA—C6GA121.9 (4)
C11X—C10X—C9X119.1 (3)C4GA—C5GA—H5GA119.0
C5X—C6X—C1X113.4 (3)C6GA—C5GA—H5GA119.0
C5X—C6X—H6X1108.9C3GA—C2GA—C1GA118.7 (3)
C1X—C6X—H6X1108.9C3GA—C2GA—C7GA120.1 (4)
C5X—C6X—H6X2108.9C1GA—C2GA—C7GA121.2 (3)
C1X—C6X—H6X2108.9C5GC—C6GC—C1GC118.0 (4)
H6X1—C6X—H6X2107.7C5GC—C6GC—C8GC119.8 (4)
C18Y—C13Y—C14Y115.3 (3)C1GC—C6GC—C8GC122.2 (3)
C18Y—C13Y—C1Y122.7 (3)C2GA—C7GA—H7A1109.5
C14Y—C13Y—C1Y121.9 (3)C2GA—C7GA—H7A2109.5
C16X—C15X—C14X119.6 (3)H7A1—C7GA—H7A2109.5
C16X—C15X—H15X120.2C2GA—C7GA—H7A3109.5
C14X—C15X—H15X120.2H7A1—C7GA—H7A3109.5
C9Y—C8Y—C7Y122.2 (3)H7A2—C7GA—H7A3109.5
C9Y—C8Y—H8Y118.9C2GA—C1GA—C6GA121.1 (3)
C7Y—C8Y—H8Y118.9C2GA—C1GA—N1GA119.2 (3)
C5GB—C6GB—C1GB119.2 (4)C6GA—C1GA—N1GA119.6 (3)
C5GB—C6GB—C8GB120.5 (4)C6GA—C8GA—H8A1109.5
C1GB—C6GB—C8GB120.3 (4)C6GA—C8GA—H8A2109.5
C5Y—C6Y—C1Y113.5 (3)H8A1—C8GA—H8A2109.5
C5Y—C6Y—H6Y1108.9C6GA—C8GA—H8A3109.5
C1Y—C6Y—H6Y1108.9H8A1—C8GA—H8A3109.5
C5Y—C6Y—H6Y2108.9H8A2—C8GA—H8A3109.5
C1Y—C6Y—H6Y2108.9C1GC—C2GC—C3GC117.3 (3)
H6Y1—C6Y—H6Y2107.7C1GC—C2GC—C7GC121.6 (3)
C6Y—C5Y—C4Y111.5 (3)C3GC—C2GC—C7GC121.1 (3)
C6Y—C5Y—H5Y1109.3C2GC—C7GC—H7C1109.5
C4Y—C5Y—H5Y1109.3C2GC—C7GC—H7C2109.5
C6Y—C5Y—H5Y2109.3H7C1—C7GC—H7C2109.5
C4Y—C5Y—H5Y2109.3C2GC—C7GC—H7C3109.5
H5Y1—C5Y—H5Y2108.0H7C1—C7GC—H7C3109.5
C4GD—C5GD—C6GD121.7 (4)H7C2—C7GC—H7C3109.5
C4GD—C5GD—H5GD119.2C4GC—C3GC—C2GC121.8 (4)
C6GD—C5GD—H5GD119.2C4GC—C3GC—H3GC119.1
C6X—C5X—C4X111.9 (3)C2GC—C3GC—H3GC119.1
C6X—C5X—H5X1109.2C6GC—C8GC—H8C1109.5
C4X—C5X—H5X1109.2C6GC—C8GC—H8C2109.5
C6X—C5X—H5X2109.2H8C1—C8GC—H8C2109.5
C4X—C5X—H5X2109.2C6GC—C8GC—H8C3109.5
H5X1—C5X—H5X2107.9H8C1—C8GC—H8C3109.5
C6GB—C5GB—C4GB121.2 (4)H8C2—C8GC—H8C3109.5
C6GB—C5GB—H5GB119.4C4GA—C3GA—C2GA121.0 (4)
C4GB—C5GB—H5GB119.4C4GA—C3GA—H3GA119.5
C5GD—C6GD—C1GD118.5 (4)C2GA—C3GA—H3GA119.5
C5GD—C6GD—C8GD121.5 (4)C4GC—C5GC—C6GC121.4 (4)
C1GD—C6GD—C8GD120.0 (4)C4GC—C5GC—H5GC119.3
C4GD—C3GD—C2GD122.0 (4)C6GC—C5GC—H5GC119.3
C4GD—C3GD—H3GD119.0C5GA—C4GA—C3GA119.7 (4)
C2GD—C3GD—H3GD119.0C5GA—C4GA—H4GA120.2
C8Y—C9Y—C10Y120.4 (3)C3GA—C4GA—H4GA120.2
C8Y—C9Y—H9Y119.8C5GC—C4GC—C3GC119.6 (4)
C10Y—C9Y—H9Y119.8C5GC—C4GC—H4GC120.2
C3GD—C4GD—C5GD118.7 (4)C3GC—C4GC—H4GC120.2
C3GD—C4GD—H4GD120.6C1GF—N1GF—H1F1113 (2)
C5GD—C4GD—H4GD120.6C1GF—N1GF—H1F2116 (2)
C4X—C3X—C2X111.5 (3)H1F1—N1GF—H1F2116 (3)
C4X—C3X—H3X1109.3C6GF—C1GF—C2GF121.1 (3)
C2X—C3X—H3X1109.3C6GF—C1GF—N1GF120.1 (3)
C4X—C3X—H3X2109.3C2GF—C1GF—N1GF118.7 (3)
C2X—C3X—H3X2109.3C4GF—C5GF—C6GF121.7 (4)
H3X1—C3X—H3X2108.0C4GF—C5GF—H5GF119.2
C5Y—C4Y—C3Y110.0 (3)C6GF—C5GF—H5GF119.2
C5Y—C4Y—H4Y1109.7C3GF—C2GF—C1GF118.9 (4)
C3Y—C4Y—H4Y1109.7C3GF—C2GF—C7GF120.8 (4)
C5Y—C4Y—H4Y2109.7C1GF—C2GF—C7GF120.3 (3)
C3Y—C4Y—H4Y2109.7C5GF—C6GF—C1GF117.3 (3)
H4Y1—C4Y—H4Y2108.2C5GF—C6GF—C8GF121.6 (3)
C1GD—N1GD—H1D1122 (3)C1GF—C6GF—C8GF121.1 (3)
C1GD—N1GD—H1D2116 (3)C2GF—C7GF—H7F1109.5
H1D1—N1GD—H1D2111 (4)C2GF—C7GF—H7F3109.5
C15Y—C14Y—C13Y122.2 (3)H7F1—C7GF—H7F3109.5
C15Y—C14Y—H14Y118.9C2GF—C7GF—H7F2109.5
C13Y—C14Y—H14Y118.9H7F1—C7GF—H7F2109.5
C2Y—C3Y—C4Y110.7 (3)H7F3—C7GF—H7F2109.5
C2Y—C3Y—H3Y1109.5C6GF—C8GF—H8F1109.5
C4Y—C3Y—H3Y1109.5C6GF—C8GF—H8F2109.5
C2Y—C3Y—H3Y2109.5H8F1—C8GF—H8F2109.5
C4Y—C3Y—H3Y2109.5C6GF—C8GF—H8F3109.5
H3Y1—C3Y—H3Y2108.1H8F1—C8GF—H8F3109.5
C3GD—C2GD—C1GD119.0 (4)H8F2—C8GF—H8F3109.5
C3GD—C2GD—C7GD120.7 (4)C4GF—C3GF—C2GF120.5 (4)
C1GD—C2GD—C7GD120.3 (3)C4GF—C3GF—H3GF119.7
C16Y—C17Y—C18Y119.8 (3)C2GF—C3GF—H3GF119.7
C16Y—C17Y—H17Y120.1C3GF—C4GF—C5GF120.4 (4)
C18Y—C17Y—H17Y120.1C3GF—C4GF—H4GF119.8
C5GB—C4GB—C3GB119.6 (4)C5GF—C4GF—H4GF119.8
C9X—C8X—C7X—C12X0.1 (5)C6Y—C5Y—C4Y—C3Y56.2 (5)
C9X—C8X—C7X—C1X176.0 (3)C16Y—C15Y—C14Y—C13Y0.9 (6)
C7X—C8X—C9X—C10X1.2 (5)C18Y—C13Y—C14Y—C15Y2.1 (5)
C8X—C7X—C12X—C11X0.7 (5)C1Y—C13Y—C14Y—C15Y176.4 (3)
C1X—C7X—C12X—C11X176.8 (3)C1Y—C2Y—C3Y—C4Y58.0 (4)
C10Y—C11Y—C12Y—C7Y0.5 (5)C5Y—C4Y—C3Y—C2Y55.5 (5)
C11Y—C12Y—C7Y—C8Y2.0 (5)C4GD—C3GD—C2GD—C1GD0.5 (5)
C11Y—C12Y—C7Y—C1Y179.4 (3)C4GD—C3GD—C2GD—C7GD179.2 (3)
C13Y—C1Y—C7Y—C8Y85.7 (4)N1GD—C1GD—C2GD—C3GD179.1 (3)
C2Y—C1Y—C7Y—C8Y152.1 (3)C6GD—C1GD—C2GD—C3GD1.1 (5)
C6Y—C1Y—C7Y—C8Y34.6 (4)N1GD—C1GD—C2GD—C7GD0.6 (5)
C13Y—C1Y—C7Y—C12Y92.8 (3)C6GD—C1GD—C2GD—C7GD178.6 (3)
C2Y—C1Y—C7Y—C12Y29.4 (4)O2Y—C16Y—C17Y—C18Y177.8 (4)
C6Y—C1Y—C7Y—C12Y146.9 (3)C15Y—C16Y—C17Y—C18Y2.6 (6)
C12X—C7X—C1X—C13X91.2 (3)C13Y—C18Y—C17Y—C16Y0.5 (6)
C8X—C7X—C1X—C13X84.6 (3)C6GB—C5GB—C4GB—C3GB0.8 (6)
C12X—C7X—C1X—C2X29.9 (4)C13X—C18X—C17X—C16X0.2 (6)
C8X—C7X—C1X—C2X154.3 (3)O2X—C16X—C17X—C18X176.8 (4)
C12X—C7X—C1X—C6X148.4 (3)C15X—C16X—C17X—C18X3.0 (6)
C8X—C7X—C1X—C6X35.8 (4)C6X—C5X—C4X—C3X55.2 (4)
C12Y—C11Y—C10Y—O1Y177.4 (3)C2X—C3X—C4X—C5X55.1 (4)
C12Y—C11Y—C10Y—C9Y1.9 (5)C5GB—C4GB—C3GB—C2GB0.4 (6)
C15X—C14X—C13X—C18X3.4 (5)C3GE—C2GE—C1GE—C6GE2.2 (6)
C15X—C14X—C13X—C1X179.7 (3)C7GE—C2GE—C1GE—C6GE176.5 (4)
C7X—C1X—C13X—C14X96.1 (3)C3GE—C2GE—C1GE—N1GE173.2 (3)
C2X—C1X—C13X—C14X25.4 (4)C7GE—C2GE—C1GE—N1GE8.1 (5)
C6X—C1X—C13X—C14X142.9 (3)C4GB—C3GB—C2GB—C1GB0.5 (5)
C7X—C1X—C13X—C18X80.7 (4)C4GB—C3GB—C2GB—C7GB179.1 (4)
C2X—C1X—C13X—C18X157.9 (3)C6GB—C1GB—C2GB—C3GB1.1 (5)
C6X—C1X—C13X—C18X40.3 (4)N1GB—C1GB—C2GB—C3GB179.2 (3)
C13X—C1X—C2X—C3X175.2 (3)C6GB—C1GB—C2GB—C7GB178.5 (4)
C7X—C1X—C2X—C3X66.6 (3)N1GB—C1GB—C2GB—C7GB0.4 (5)
C6X—C1X—C2X—C3X55.1 (3)N1GE—C1GE—C6GE—C5GE173.0 (3)
C13Y—C1Y—C2Y—C3Y172.0 (3)C2GE—C1GE—C6GE—C5GE2.5 (5)
C7Y—C1Y—C2Y—C3Y67.2 (4)N1GE—C1GE—C6GE—C8GE5.6 (6)
C6Y—C1Y—C2Y—C3Y54.9 (4)C2GE—C1GE—C6GE—C8GE178.9 (4)
O2Y—C16Y—C15Y—C14Y177.1 (4)C1GE—C2GE—C3GE—C4GE1.1 (6)
C17Y—C16Y—C15Y—C14Y3.3 (6)C7GE—C2GE—C3GE—C4GE177.6 (4)
C7X—C12X—C11X—C10X0.4 (5)C5GE—C4GE—C3GE—C2GE0.4 (6)
C14X—C13X—C18X—C17X2.9 (5)C3GE—C4GE—C5GE—C6GE0.7 (6)
C1X—C13X—C18X—C17X179.9 (3)C1GE—C6GE—C5GE—C4GE1.8 (6)
C12X—C11X—C10X—O1X177.3 (3)C8GE—C6GE—C5GE—C4GE179.6 (4)
C12X—C11X—C10X—C9X0.7 (5)C1GA—C6GA—C5GA—C4GA0.1 (6)
C8X—C9X—C10X—O1X176.6 (3)C8GA—C6GA—C5GA—C4GA179.9 (4)
C8X—C9X—C10X—C11X1.5 (5)C2GC—C1GC—C6GC—C5GC1.4 (5)
C13X—C1X—C6X—C5X175.4 (3)N1GC—C1GC—C6GC—C5GC178.5 (3)
C7X—C1X—C6X—C5X66.8 (4)C2GC—C1GC—C6GC—C8GC179.6 (3)
C2X—C1X—C6X—C5X54.9 (4)N1GC—C1GC—C6GC—C8GC2.5 (5)
C17Y—C18Y—C13Y—C14Y2.8 (6)C3GA—C2GA—C1GA—C6GA1.2 (5)
C17Y—C18Y—C13Y—C1Y175.7 (4)C7GA—C2GA—C1GA—C6GA179.1 (3)
C7Y—C1Y—C13Y—C18Y107.2 (4)C3GA—C2GA—C1GA—N1GA177.8 (3)
C2Y—C1Y—C13Y—C18Y15.2 (5)C7GA—C2GA—C1GA—N1GA2.5 (5)
C6Y—C1Y—C13Y—C18Y130.0 (4)C5GA—C6GA—C1GA—C2GA1.0 (5)
C7Y—C1Y—C13Y—C14Y74.4 (4)C8GA—C6GA—C1GA—C2GA178.9 (3)
C2Y—C1Y—C13Y—C14Y163.2 (3)C5GA—C6GA—C1GA—N1GA177.6 (3)
C6Y—C1Y—C13Y—C14Y48.4 (4)C8GA—C6GA—C1GA—N1GA2.3 (5)
O2X—C16X—C15X—C14X177.3 (3)C6GC—C1GC—C2GC—C3GC0.8 (5)
C17X—C16X—C15X—C14X2.5 (5)N1GC—C1GC—C2GC—C3GC178.0 (3)
C13X—C14X—C15X—C16X0.7 (5)C6GC—C1GC—C2GC—C7GC178.9 (3)
C12Y—C7Y—C8Y—C9Y1.1 (6)N1GC—C1GC—C2GC—C7GC1.8 (5)
C1Y—C7Y—C8Y—C9Y179.7 (4)C1GC—C2GC—C3GC—C4GC0.3 (6)
C2GB—C1GB—C6GB—C5GB0.7 (5)C7GC—C2GC—C3GC—C4GC180.0 (4)
N1GB—C1GB—C6GB—C5GB178.8 (3)C1GA—C2GA—C3GA—C4GA0.2 (6)
C2GB—C1GB—C6GB—C8GB178.9 (4)C7GA—C2GA—C3GA—C4GA179.9 (4)
N1GB—C1GB—C6GB—C8GB0.8 (5)C1GC—C6GC—C5GC—C4GC0.8 (6)
C13Y—C1Y—C6Y—C5Y172.6 (3)C8GC—C6GC—C5GC—C4GC179.8 (4)
C7Y—C1Y—C6Y—C5Y67.3 (4)C6GA—C5GA—C4GA—C3GA1.1 (7)
C2Y—C1Y—C6Y—C5Y54.0 (4)C2GA—C3GA—C4GA—C5GA0.9 (7)
C1Y—C6Y—C5Y—C4Y58.1 (5)C6GC—C5GC—C4GC—C3GC0.3 (7)
C1X—C6X—C5X—C4X57.5 (4)C2GC—C3GC—C4GC—C5GC0.8 (7)
C1GB—C6GB—C5GB—C4GB0.2 (5)C6GF—C1GF—C2GF—C3GF3.3 (5)
C8GB—C6GB—C5GB—C4GB179.8 (4)N1GF—C1GF—C2GF—C3GF179.1 (3)
C4GD—C5GD—C6GD—C1GD0.1 (5)C6GF—C1GF—C2GF—C7GF178.2 (3)
C4GD—C5GD—C6GD—C8GD177.8 (4)N1GF—C1GF—C2GF—C7GF0.6 (5)
C2GD—C1GD—C6GD—C5GD0.7 (5)C4GF—C5GF—C6GF—C1GF0.2 (6)
N1GD—C1GD—C6GD—C5GD178.8 (3)C4GF—C5GF—C6GF—C8GF179.2 (4)
C2GD—C1GD—C6GD—C8GD178.7 (3)C2GF—C1GF—C6GF—C5GF2.7 (5)
N1GD—C1GD—C6GD—C8GD3.3 (5)N1GF—C1GF—C6GF—C5GF179.7 (3)
C7Y—C8Y—C9Y—C10Y1.3 (7)C2GF—C1GF—C6GF—C8GF178.3 (3)
O1Y—C10Y—C9Y—C8Y176.5 (4)N1GF—C1GF—C6GF—C8GF0.7 (5)
C11Y—C10Y—C9Y—C8Y2.9 (6)C1GF—C2GF—C3GF—C4GF1.4 (6)
C2GD—C3GD—C4GD—C5GD0.3 (5)C7GF—C2GF—C3GF—C4GF179.8 (4)
C6GD—C5GD—C4GD—C3GD0.7 (5)C2GF—C3GF—C4GF—C5GF1.1 (6)
C1X—C2X—C3X—C4X57.7 (4)C6GF—C5GF—C4GF—C3GF1.7 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1X—H1X···N1GAi0.95 (2)1.83 (2)2.781 (4)174 (4)
O1Y—H1Y···N1GCii0.94 (2)1.92 (2)2.819 (4)159 (4)
O2X—H2X···N1GE0.91 (2)1.93 (2)2.835 (4)171 (5)
O2Y—H2Y···N1GFii0.95 (2)1.87 (2)2.801 (4)166 (4)
N1GA—H1A2···O1Xiii0.93 (2)2.13 (3)3.025 (4)161 (3)
N1GE—H1E2···O2Xiv0.94 (2)2.24 (3)3.115 (4)155 (3)
N1GF—H1F2···O1Yv0.93 (2)2.24 (2)3.147 (4)165 (3)
N1GC—H1C2···O2Yvi0.99 (2)2.11 (2)3.042 (4)157 (3)
Symmetry codes: (i) x1, y, z; (ii) x1, y+1, z; (iii) x+1, y+1, z; (iv) x, y+2, z; (v) x+1/2, y3/2, z+1/2; (vi) x+1/2, y1/2, z+1/2.
(dc23x0.5) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 2,3-xylidine top
Crystal data top
C18H20O2/0.5(C8H11N)F(000) = 1416
Mr = 328.93Dx = 1.214 Mg m3
Dm = N/A Mg m3
Dm measured by not measured
Monoclinic, C2/cMelting point: 412.95K fro guest release onset temp. and 463.15K for host melting K
a = 18.1704 (10) ÅMo Kα radiation, λ = 0.71069 Å
b = 12.2744 (10) ŵ = 0.08 mm1
c = 16.2036 (10) ÅT = 173 K
β = 95.30 (3)°Cuboid, colourless
V = 3598.5 (4) Å30.40 × 0.40 × 0.30 mm
Z = 8
Data collection top
Nonius Kappa CCD
diffractometer
2558 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.3°, θmin = 3.2°
φ scans and ω scansh = 2120
9719 measured reflectionsk = 1413
3283 independent reflectionsl = 1917
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.035H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090 w = 1/[σ2(Fo2) + (0.0402P)2 + 1.4007P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max = 0.010
3283 reflectionsΔρmax = 0.18 e Å3
288 parametersΔρmin = 0.16 e Å3
13 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0027 (3)
Special details top

Experimental. Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40 mm; combination of φ and ω scans of 1°, 60 s per °, 2 iterations.

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)
O10.01908 (6)0.27005 (8)0.17142 (6)0.0443 (3)
O20.44209 (6)0.57211 (8)0.12302 (7)0.0485 (3)
C70.14417 (7)0.40093 (9)0.00027 (7)0.0256 (3)
C170.33178 (7)0.61808 (10)0.06122 (7)0.0307 (3)
H170.33290.68930.08400.037*
C130.27099 (6)0.48452 (9)0.02053 (7)0.0248 (3)
C90.10168 (7)0.34588 (10)0.13998 (7)0.0312 (3)
H90.11090.33900.19650.037*
C10.20352 (7)0.44860 (10)0.06455 (7)0.0263 (3)
C140.32842 (7)0.41328 (10)0.00715 (8)0.0306 (3)
H140.32830.34250.03080.037*
C80.15542 (7)0.38957 (10)0.08290 (7)0.0281 (3)
H80.20110.41230.10130.034*
C180.27476 (7)0.58791 (10)0.01477 (7)0.0291 (3)
H180.23700.63930.00670.035*
C30.27854 (8)0.40330 (11)0.20184 (8)0.0378 (3)
H310.28820.34550.24400.045*
H320.32600.42190.17980.045*
C100.03519 (7)0.31264 (10)0.11470 (7)0.0309 (3)
C150.38561 (7)0.44196 (11)0.03937 (8)0.0344 (3)
H150.42380.39120.04720.041*
C20.22454 (7)0.36076 (10)0.13152 (7)0.0297 (3)
H210.17910.33510.15470.036*
H220.24700.29770.10520.036*
C60.17024 (7)0.54543 (10)0.10976 (8)0.0319 (3)
H610.15620.60380.06910.038*
H620.12480.52100.13370.038*
C110.02235 (8)0.32228 (12)0.03250 (8)0.0389 (3)
H110.02340.29910.01450.047*
C120.07633 (7)0.36583 (12)0.02376 (8)0.0364 (3)
H120.06680.37200.08020.044*
C160.38702 (7)0.54460 (10)0.07446 (7)0.0309 (3)
C50.22429 (8)0.59133 (11)0.17875 (8)0.0394 (3)
H510.26830.62050.15460.047*
H520.20050.65200.20650.047*
C40.24813 (9)0.50364 (12)0.24227 (8)0.0431 (4)
H410.28650.53370.28330.052*
H420.20520.48230.27210.052*
N1G0.04794 (19)0.0560 (3)0.3235 (2)0.0512 (9)0.50
C1G0.0347 (2)0.1689 (3)0.3024 (3)0.0361 (8)0.50
C5G0.0610 (4)0.3583 (7)0.3267 (5)0.0580 (18)0.50
H5G0.08870.41460.35530.070*0.50
C3G0.03287 (19)0.3044 (3)0.2209 (2)0.0458 (8)0.50
C6G0.07526 (17)0.2494 (3)0.34677 (18)0.0464 (7)0.50
H6G0.11200.23050.38990.056*0.50
C8G0.0917 (4)0.3359 (7)0.1538 (5)0.067 (2)0.50
H8G10.14060.32210.17270.101*0.50
H8G20.08600.29260.10400.101*0.50
H8G30.08700.41340.14090.101*0.50
C2G0.0198 (2)0.1954 (3)0.2403 (3)0.0366 (11)0.50
C4G0.0054 (17)0.3840 (3)0.2638 (11)0.064 (5)0.50
H4G0.00560.45820.25120.077*0.50
C7G0.0642 (3)0.1069 (5)0.1953 (3)0.0523 (10)0.50
H7G10.10240.13960.15640.078*0.50
H7G20.08760.06190.23550.078*0.50
H7G30.03160.06150.16480.078*0.50
H1A0.0314 (18)0.1990 (16)0.153 (2)0.063 (10)*0.50
H1B0.008 (3)0.270 (3)0.2279 (14)0.093 (13)*0.50
H2B0.440 (2)0.6470 (18)0.140 (3)0.108 (16)*0.50
H2A0.4782 (16)0.515 (3)0.134 (2)0.082 (12)*0.50
H1G10.051 (2)0.0214 (19)0.2732 (14)0.098*0.50
H1G20.0889 (17)0.057 (2)0.3632 (17)0.098*0.50
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0501 (6)0.0439 (6)0.0357 (6)0.0174 (5)0.0139 (5)0.0071 (4)
O20.0442 (6)0.0413 (6)0.0641 (7)0.0039 (5)0.0266 (5)0.0078 (5)
C70.0296 (7)0.0223 (6)0.0248 (6)0.0009 (5)0.0022 (5)0.0024 (5)
C170.0392 (8)0.0215 (6)0.0318 (7)0.0030 (6)0.0047 (6)0.0023 (5)
C130.0276 (7)0.0235 (6)0.0229 (6)0.0010 (5)0.0002 (5)0.0012 (5)
C90.0383 (8)0.0322 (7)0.0235 (6)0.0013 (6)0.0036 (5)0.0023 (5)
C10.0299 (7)0.0254 (6)0.0240 (6)0.0004 (5)0.0035 (5)0.0001 (5)
C140.0328 (7)0.0235 (7)0.0356 (7)0.0013 (6)0.0037 (5)0.0049 (5)
C80.0288 (7)0.0286 (7)0.0273 (6)0.0009 (5)0.0042 (5)0.0030 (5)
C180.0342 (7)0.0235 (7)0.0298 (6)0.0022 (6)0.0032 (5)0.0004 (5)
C30.0439 (8)0.0421 (8)0.0266 (7)0.0033 (7)0.0021 (6)0.0054 (6)
C100.0357 (8)0.0273 (7)0.0285 (7)0.0044 (6)0.0038 (5)0.0057 (5)
C150.0299 (7)0.0303 (7)0.0440 (8)0.0042 (6)0.0080 (6)0.0023 (6)
C20.0346 (7)0.0285 (7)0.0262 (6)0.0018 (6)0.0042 (5)0.0025 (5)
C60.0343 (7)0.0303 (7)0.0320 (7)0.0003 (6)0.0084 (5)0.0017 (5)
C110.0323 (7)0.0524 (9)0.0322 (7)0.0122 (7)0.0043 (6)0.0043 (6)
C120.0366 (8)0.0483 (8)0.0250 (6)0.0071 (6)0.0064 (5)0.0003 (6)
C160.0310 (7)0.0298 (7)0.0325 (7)0.0063 (6)0.0057 (5)0.0006 (5)
C50.0490 (9)0.0355 (8)0.0349 (7)0.0053 (7)0.0110 (6)0.0113 (6)
C40.0524 (9)0.0496 (9)0.0271 (7)0.0108 (7)0.0026 (6)0.0068 (6)
N1G0.0338 (18)0.042 (2)0.079 (2)0.0088 (15)0.0115 (15)0.0188 (17)
C1G0.027 (2)0.030 (2)0.053 (2)0.0024 (17)0.013 (2)0.0040 (18)
C5G0.063 (5)0.048 (3)0.067 (5)0.010 (3)0.027 (3)0.009 (3)
C3G0.054 (2)0.044 (2)0.0430 (18)0.0119 (18)0.0225 (14)0.0113 (16)
C6G0.0376 (18)0.057 (2)0.0456 (18)0.0044 (16)0.0093 (14)0.0051 (15)
C8G0.082 (5)0.066 (5)0.056 (3)0.032 (4)0.018 (4)0.017 (3)
C2G0.029 (3)0.0385 (18)0.043 (3)0.0015 (13)0.009 (3)0.003 (2)
C4G0.090 (8)0.0349 (17)0.077 (12)0.010 (4)0.052 (10)0.002 (2)
C7G0.041 (3)0.052 (3)0.062 (3)0.005 (2)0.0040 (19)0.010 (2)
Geometric parameters (Å, º) top
O1—C101.3867 (15)C2—H220.9900
O1—H1A0.955 (14)C6—C51.5261 (18)
O1—H1B0.953 (14)C6—H610.9900
O2—C161.3710 (16)C6—H620.9900
O2—H2B0.960 (17)C11—C121.3833 (18)
O2—H2A0.992 (15)C11—H110.9500
C7—C81.3887 (17)C12—H120.9500
C7—C121.3916 (18)C5—C41.524 (2)
C7—C11.5435 (17)C5—H510.9900
C17—C161.3810 (18)C5—H520.9900
C17—C181.3859 (18)C4—H410.9900
C17—H170.9500C4—H420.9900
C13—C141.3936 (17)N1G—C1G1.442 (5)
C13—C181.3962 (17)N1G—H1G10.926 (17)
C13—C11.5388 (17)N1G—H1G20.938 (17)
C9—C101.3731 (18)C1G—C2G1.383 (7)
C9—C81.3891 (17)C1G—C6G1.392 (5)
C9—H90.9500C5G—C6G1.394 (9)
C1—C61.5482 (17)C5G—C4G1.40 (3)
C1—C21.5523 (16)C5G—H5G0.9500
C14—C151.3844 (18)C3G—C4G1.353 (19)
C14—H140.9500C3G—C2G1.390 (5)
C8—H80.9500C3G—C8G1.504 (8)
C18—H180.9500C6G—H6G0.9500
C3—C41.523 (2)C8G—H8G10.9800
C3—C21.5255 (17)C8G—H8G20.9800
C3—H310.9900C8G—H8G30.9800
C3—H320.9900C2G—C7G1.501 (6)
C10—C111.3785 (18)C4G—H4G0.9500
C15—C161.3834 (18)C7G—H7G10.9800
C15—H150.9500C7G—H7G20.9800
C2—H210.9900C7G—H7G30.9800
C10—O1—H1A108 (2)H21—C2—H22107.8
C10—O1—H1B116 (3)C5—C6—C1112.15 (10)
H1A—O1—H1B112 (3)C5—C6—H61109.2
C16—O2—H2B113 (2)C1—C6—H61109.2
C16—O2—H2A117 (2)C5—C6—H62109.2
H2B—O2—H2A130 (3)C1—C6—H62109.2
C8—C7—C12116.61 (11)H61—C6—H62107.9
C8—C7—C1122.45 (11)C10—C11—C12119.80 (12)
C12—C7—C1120.94 (10)C10—C11—H11120.1
C16—C17—C18120.02 (11)C12—C11—H11120.1
C16—C17—H17120.0C11—C12—C7122.10 (11)
C18—C17—H17120.0C11—C12—H12118.9
C14—C13—C18116.16 (11)C7—C12—H12118.9
C14—C13—C1122.17 (11)O2—C16—C17120.52 (11)
C18—C13—C1121.44 (11)O2—C16—C15120.16 (12)
C10—C9—C8120.00 (11)C17—C16—C15119.31 (12)
C10—C9—H9120.0C4—C5—C6110.95 (11)
C8—C9—H9120.0C4—C5—H51109.4
C13—C1—C7109.44 (9)C6—C5—H51109.4
C13—C1—C6111.23 (10)C4—C5—H52109.4
C7—C1—C6109.35 (10)C6—C5—H52109.4
C13—C1—C2111.58 (10)H51—C5—H52108.0
C7—C1—C2108.66 (10)C3—C4—C5111.87 (11)
C6—C1—C2106.50 (9)C3—C4—H41109.2
C15—C14—C13122.38 (12)C5—C4—H41109.2
C15—C14—H14118.8C3—C4—H42109.2
C13—C14—H14118.8C5—C4—H42109.2
C7—C8—C9121.83 (12)H41—C4—H42107.9
C7—C8—H8119.1C1G—N1G—H1G1104.8 (17)
C9—C8—H8119.1C1G—N1G—H1G2105.1 (16)
C17—C18—C13122.19 (12)H1G1—N1G—H1G2120 (3)
C17—C18—H18118.9C2G—C1G—C6G121.2 (4)
C13—C18—H18118.9C2G—C1G—N1G119.4 (4)
C4—C3—C2111.36 (11)C6G—C1G—N1G119.4 (4)
C4—C3—H31109.4C6G—C5G—C4G119.4 (8)
C2—C3—H31109.4C6G—C5G—H5G120.3
C4—C3—H32109.4C4G—C5G—H5G120.3
C2—C3—H32109.4C4G—C3G—C2G120.7 (9)
H31—C3—H32108.0C4G—C3G—C8G118.9 (8)
C9—C10—C11119.65 (12)C2G—C3G—C8G120.4 (5)
C9—C10—O1120.38 (11)C1G—C6G—C5G118.8 (4)
C11—C10—O1119.96 (12)C1G—C6G—H6G120.6
C16—C15—C14119.92 (12)C5G—C6G—H6G120.6
C16—C15—H15120.0C1G—C2G—C3G119.1 (4)
C14—C15—H15120.0C1G—C2G—C7G120.0 (4)
C3—C2—C1112.60 (10)C3G—C2G—C7G120.9 (3)
C3—C2—H21109.1C3G—C4G—C5G120.8 (7)
C1—C2—H21109.1C3G—C4G—H4G119.6
C3—C2—H22109.1C5G—C4G—H4G119.6
C1—C2—H22109.1
C14—C13—C1—C787.60 (13)C7—C1—C6—C5175.81 (10)
C18—C13—C1—C786.60 (13)C2—C1—C6—C558.57 (13)
C14—C13—C1—C6151.47 (11)C9—C10—C11—C120.3 (2)
C18—C13—C1—C634.33 (14)O1—C10—C11—C12179.35 (13)
C14—C13—C1—C232.69 (15)C10—C11—C12—C70.0 (2)
C18—C13—C1—C2153.11 (10)C8—C7—C12—C110.3 (2)
C8—C7—C1—C133.01 (15)C1—C7—C12—C11179.66 (12)
C12—C7—C1—C13177.72 (11)C18—C17—C16—O2177.41 (11)
C8—C7—C1—C6125.07 (12)C18—C17—C16—C151.47 (18)
C12—C7—C1—C655.65 (15)C14—C15—C16—O2177.68 (12)
C8—C7—C1—C2119.06 (12)C14—C15—C16—C171.20 (19)
C12—C7—C1—C260.22 (15)C1—C6—C5—C458.15 (14)
C18—C13—C14—C150.92 (18)C2—C3—C4—C552.89 (16)
C1—C13—C14—C15173.56 (11)C6—C5—C4—C353.76 (16)
C12—C7—C8—C90.28 (18)C2G—C1G—C6G—C5G1.0 (6)
C1—C7—C8—C9179.59 (11)N1G—C1G—C6G—C5G178.9 (5)
C10—C9—C8—C70.08 (19)C4G—C5G—C6G—C1G1.3 (15)
C16—C17—C18—C130.53 (18)C6G—C1G—C2G—C3G1.3 (5)
C14—C13—C18—C170.65 (17)N1G—C1G—C2G—C3G179.2 (4)
C1—C13—C18—C17173.88 (11)C6G—C1G—C2G—C7G178.1 (4)
C8—C9—C10—C110.39 (19)N1G—C1G—C2G—C7G0.2 (6)
C8—C9—C10—O1179.29 (11)C4G—C3G—C2G—C1G2.0 (14)
C13—C14—C15—C160.02 (19)C8G—C3G—C2G—C1G179.9 (5)
C4—C3—C2—C156.33 (14)C4G—C3G—C2G—C7G177.4 (13)
C13—C1—C2—C363.86 (13)C8G—C3G—C2G—C7G0.5 (7)
C7—C1—C2—C3175.39 (10)C2G—C3G—C4G—C5G2 (3)
C6—C1—C2—C357.70 (13)C8G—C3G—C4G—C5G179.7 (15)
C13—C1—C6—C563.21 (13)C6G—C5G—C4G—C3G2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···O2i0.96 (1)1.71 (1)2.6680 (14)177 (3)
O1—H1B···O1ii0.95 (1)1.75 (1)2.700 (2)176 (5)
O2—H2A···N1Giii0.99 (2)1.73 (2)2.689 (4)162 (3)
O2—H2B···O1iv0.96 (2)1.78 (2)2.6680 (14)153 (3)
Symmetry codes: (i) x+1/2, y1/2, z; (ii) x, y, z+1/2; (iii) x1/2, y+1/2, z+1/2; (iv) x1/2, y+1/2, z.
(dc23x2) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 2,3-xylidine top
Crystal data top
C18H20O2/2(C8H11N)Z = 2
Mr = 510.70F(000) = 552
Triclinic, P1Dx = 1.186 Mg m3
Dm = N/A Mg m3
Dm measured by not measured
a = 6.3593 (3) ÅMelting point: 346.55K fro guest release onset temp. and 463.15K for host melting K
b = 10.8368 (5) ÅMo Kα radiation, λ = 0.71069 Å
c = 21.7366 (11) ŵ = 0.07 mm1
α = 93.429 (3)°T = 173 K
β = 91.100 (3)°Prism, colourless
γ = 106.912 (3)°0.50 × 0.40 × 0.30 mm
V = 1429.57 (12) Å3
Data collection top
Nonius Kappa CCD
diffractometer
3292 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.018
Graphite monochromatorθmax = 26.3°, θmin = 3.3°
φ scans and ω scansh = 77
6145 measured reflectionsk = 1313
4517 independent reflectionsl = 2622
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.120 w = 1/[σ2(Fo2) + (0.0553P)2 + 0.3573P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
4517 reflectionsΔρmax = 0.21 e Å3
371 parametersΔρmin = 0.18 e Å3
10 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.021 (2)
Special details top

Experimental. Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 45 mm; combination of φ and ω scans of 1°, 80 s per °, 2 iterations.

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)
O10.5590 (2)0.78196 (12)0.22041 (6)0.0362 (3)
O20.2785 (2)0.07316 (12)0.23413 (6)0.0350 (4)
C90.2727 (3)0.64108 (17)0.15268 (9)0.0291 (4)
H90.18470.69810.15750.035*
C10.2387 (3)0.31170 (15)0.06770 (8)0.0242 (4)
C20.3900 (3)0.31687 (16)0.01209 (8)0.0269 (4)
H210.39520.39490.01000.032*
H220.54110.32550.02780.032*
C100.4753 (3)0.67120 (16)0.18270 (8)0.0271 (4)
C120.5243 (3)0.47490 (17)0.13756 (9)0.0311 (5)
H120.61390.41880.13250.037*
C130.2449 (3)0.20332 (15)0.10984 (8)0.0234 (4)
C80.1967 (3)0.52741 (16)0.11538 (8)0.0270 (4)
H80.05670.50860.09480.032*
C70.3180 (3)0.44035 (15)0.10712 (8)0.0240 (4)
C160.2618 (3)0.01733 (16)0.19399 (8)0.0269 (4)
C150.4211 (3)0.05187 (16)0.15058 (9)0.0291 (4)
H150.53700.01300.14890.035*
C170.0942 (3)0.07449 (16)0.19541 (8)0.0287 (4)
H170.01670.05110.22480.034*
C60.0047 (3)0.29067 (16)0.03997 (9)0.0273 (4)
H610.09890.28390.07390.033*
H620.00210.36690.01730.033*
C140.4112 (3)0.14324 (16)0.10953 (9)0.0277 (4)
H140.52190.16580.08010.033*
C50.0731 (3)0.16994 (17)0.00361 (9)0.0330 (5)
H520.22360.16110.01990.040*
H510.07820.09280.01920.040*
C180.0873 (3)0.16597 (16)0.15415 (8)0.0273 (4)
H180.02890.20460.15610.033*
C110.6028 (3)0.58784 (17)0.17472 (9)0.0326 (5)
H110.74400.60820.19480.039*
C30.3159 (3)0.19829 (17)0.03357 (9)0.0301 (4)
H310.41450.21040.06880.036*
H320.32660.12100.01310.036*
C40.0805 (3)0.17675 (18)0.05710 (9)0.0350 (5)
H420.03190.09520.08350.042*
H410.07360.24840.08250.042*
N1GA0.9441 (3)0.84666 (16)0.31320 (8)0.0356 (4)
C1GA0.9539 (3)0.95632 (17)0.35436 (9)0.0298 (5)
C2GA1.1155 (3)0.99578 (17)0.40176 (9)0.0309 (5)
C3GA1.1276 (3)1.10706 (18)0.43950 (9)0.0356 (5)
C6GA0.8077 (3)1.02710 (19)0.34425 (9)0.0364 (5)
H6GA0.69820.99970.31190.044*
C7GA1.2707 (3)0.9169 (2)0.41274 (10)0.0426 (5)
H7A11.20590.85050.44120.064*
H7A21.41060.97350.43070.064*
H7A31.29650.87540.37350.064*
C5GA0.8221 (3)1.1376 (2)0.38140 (10)0.0423 (5)
H5GA0.72281.18650.37450.051*
C4GA0.9807 (3)1.17706 (19)0.42855 (10)0.0405 (5)
H4GA0.98941.25310.45390.049*
C8GA1.2955 (4)1.1506 (2)0.49204 (10)0.0486 (6)
H8A11.27591.22770.51420.073*
H8A21.44361.17110.47580.073*
H8A31.27641.08130.52030.073*
C2GB0.8197 (4)0.4344 (2)0.31847 (10)0.0462 (6)
C3GB0.6093 (4)0.3884 (2)0.34114 (11)0.0478 (6)
C1GB0.9867 (4)0.5202 (2)0.35533 (11)0.0487 (6)
C5GB0.7379 (5)0.5069 (2)0.43806 (12)0.0637 (8)
H5GB0.71130.52990.47940.076*
C8GB0.4296 (4)0.2976 (2)0.30512 (12)0.0593 (7)
H8B10.29670.27760.32920.089*0.50
H8B20.46850.21800.29460.089*0.50
H8B30.40230.33600.26720.089*0.50
H8B40.48160.27680.26480.089*0.50
H8B50.30990.33640.29940.089*0.50
H8B60.37600.21840.32690.089*0.50
C4GB0.5705 (4)0.4266 (2)0.40135 (11)0.0542 (6)
H6GB0.42720.39670.41690.065*
N1GB1.2056 (5)0.5777 (3)0.33197 (15)0.0827 (8)
C6GB0.9450 (5)0.5546 (2)0.41538 (12)0.0592 (7)
H4GB1.05970.61140.44100.071*
C7GB0.8717 (5)0.3866 (3)0.25551 (11)0.0722 (8)
H7B10.95400.32380.26010.108*
H7B20.96050.45970.23400.108*
H7B30.73440.34520.23160.108*
H1A10.979 (3)0.7826 (17)0.3352 (10)0.056 (7)*
H10.455 (3)0.8326 (19)0.2250 (11)0.062 (7)*
H1A20.806 (3)0.816 (2)0.2903 (9)0.057 (7)*
H20.152 (3)0.098 (2)0.2607 (11)0.087 (9)*
H1B11.327 (6)0.618 (4)0.3634 (17)0.18 (2)*
H1B21.251 (6)0.508 (3)0.3081 (16)0.135 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0357 (8)0.0294 (7)0.0430 (9)0.0117 (6)0.0089 (7)0.0085 (6)
O20.0456 (8)0.0354 (7)0.0313 (8)0.0215 (6)0.0064 (7)0.0097 (6)
C90.0289 (10)0.0270 (9)0.0345 (11)0.0132 (8)0.0010 (9)0.0011 (9)
C10.0217 (9)0.0213 (8)0.0277 (10)0.0037 (7)0.0005 (8)0.0006 (8)
C20.0258 (9)0.0247 (9)0.0292 (11)0.0053 (8)0.0004 (8)0.0049 (8)
C100.0292 (10)0.0227 (9)0.0275 (11)0.0053 (8)0.0013 (8)0.0005 (8)
C120.0284 (10)0.0278 (10)0.0395 (12)0.0130 (8)0.0039 (9)0.0018 (9)
C130.0227 (9)0.0218 (8)0.0245 (10)0.0056 (7)0.0020 (8)0.0023 (7)
C80.0229 (9)0.0277 (9)0.0301 (11)0.0074 (8)0.0038 (8)0.0006 (8)
C70.0229 (9)0.0233 (9)0.0256 (10)0.0059 (8)0.0015 (8)0.0046 (8)
C160.0350 (10)0.0231 (9)0.0230 (10)0.0098 (8)0.0011 (8)0.0003 (8)
C150.0276 (10)0.0281 (9)0.0332 (11)0.0114 (8)0.0002 (9)0.0002 (8)
C170.0330 (10)0.0302 (10)0.0246 (10)0.0117 (8)0.0076 (8)0.0017 (8)
C60.0249 (9)0.0251 (9)0.0313 (11)0.0060 (8)0.0015 (8)0.0042 (8)
C140.0248 (9)0.0276 (9)0.0300 (11)0.0060 (8)0.0048 (8)0.0042 (8)
C50.0261 (10)0.0301 (10)0.0387 (12)0.0029 (8)0.0088 (9)0.0007 (9)
C180.0294 (10)0.0290 (9)0.0263 (10)0.0134 (8)0.0023 (8)0.0003 (8)
C110.0268 (10)0.0318 (10)0.0387 (12)0.0097 (8)0.0087 (9)0.0031 (9)
C30.0319 (10)0.0297 (10)0.0262 (11)0.0052 (8)0.0025 (8)0.0015 (8)
C40.0386 (11)0.0321 (10)0.0312 (11)0.0071 (9)0.0056 (9)0.0033 (9)
N1GA0.0395 (10)0.0344 (9)0.0335 (10)0.0114 (8)0.0018 (9)0.0043 (8)
C1GA0.0311 (10)0.0325 (10)0.0260 (11)0.0082 (9)0.0058 (9)0.0078 (8)
C2GA0.0307 (10)0.0330 (10)0.0284 (11)0.0071 (9)0.0030 (9)0.0085 (9)
C3GA0.0381 (11)0.0352 (11)0.0305 (12)0.0046 (9)0.0058 (9)0.0088 (9)
C6GA0.0342 (11)0.0453 (12)0.0317 (12)0.0136 (9)0.0019 (9)0.0085 (10)
C7GA0.0367 (11)0.0459 (12)0.0450 (13)0.0116 (10)0.0023 (10)0.0052 (10)
C5GA0.0445 (12)0.0455 (12)0.0450 (14)0.0234 (10)0.0085 (11)0.0125 (11)
C4GA0.0495 (13)0.0355 (11)0.0368 (13)0.0122 (10)0.0081 (11)0.0030 (10)
C8GA0.0515 (14)0.0495 (13)0.0385 (13)0.0054 (11)0.0041 (11)0.0018 (11)
C2GB0.0786 (17)0.0407 (12)0.0325 (13)0.0369 (12)0.0049 (12)0.0075 (10)
C3GB0.0718 (16)0.0379 (12)0.0391 (13)0.0253 (12)0.0058 (12)0.0013 (10)
C1GB0.0678 (16)0.0347 (11)0.0498 (15)0.0227 (12)0.0110 (13)0.0098 (11)
C5GB0.095 (2)0.0474 (14)0.0395 (14)0.0066 (14)0.0189 (15)0.0055 (12)
C8GB0.0668 (16)0.0518 (14)0.0579 (17)0.0180 (13)0.0234 (14)0.0035 (13)
C4GB0.0693 (16)0.0439 (13)0.0461 (15)0.0111 (12)0.0102 (13)0.0023 (11)
N1GB0.0751 (17)0.0716 (16)0.108 (2)0.0284 (14)0.0258 (17)0.0164 (16)
C6GB0.0830 (18)0.0391 (12)0.0488 (15)0.0092 (13)0.0001 (14)0.0052 (11)
C7GB0.114 (2)0.0894 (19)0.0383 (15)0.0692 (18)0.0037 (15)0.0021 (14)
Geometric parameters (Å, º) top
O1—C101.375 (2)N1GA—H1A10.941 (14)
O1—H10.980 (13)N1GA—H1A20.958 (13)
O2—C161.376 (2)C1GA—C6GA1.388 (3)
O2—H20.983 (13)C1GA—C2GA1.397 (3)
C9—C101.374 (3)C2GA—C3GA1.399 (3)
C9—C81.388 (2)C2GA—C7GA1.506 (3)
C9—H90.9500C3GA—C4GA1.389 (3)
C1—C71.537 (2)C3GA—C8GA1.504 (3)
C1—C131.541 (2)C6GA—C5GA1.383 (3)
C1—C61.544 (2)C6GA—H6GA0.9500
C1—C21.553 (2)C7GA—H7A10.9800
C2—C31.528 (2)C7GA—H7A20.9800
C2—H210.9900C7GA—H7A30.9800
C2—H220.9900C5GA—C4GA1.381 (3)
C10—C111.384 (2)C5GA—H5GA0.9500
C12—C111.382 (3)C4GA—H4GA0.9500
C12—C71.397 (2)C8GA—H8A10.9800
C12—H120.9500C8GA—H8A20.9800
C13—C141.393 (2)C8GA—H8A30.9800
C13—C181.394 (2)C2GB—C1GB1.392 (3)
C8—C71.388 (2)C2GB—C3GB1.396 (3)
C8—H80.9500C2GB—C7GB1.511 (3)
C16—C171.379 (2)C3GB—C4GB1.397 (3)
C16—C151.384 (2)C3GB—C8GB1.451 (3)
C15—C141.386 (2)C1GB—C6GB1.388 (3)
C15—H150.9500C1GB—N1GB1.464 (3)
C17—C181.385 (2)C5GB—C4GB1.368 (4)
C17—H170.9500C5GB—C6GB1.380 (3)
C6—C51.520 (3)C5GB—H5GB0.9500
C6—H610.9900C8GB—H8B10.9800
C6—H620.9900C8GB—H8B20.9800
C14—H140.9500C8GB—H8B30.9800
C5—C41.524 (3)C8GB—H8B40.9800
C5—H520.9900C8GB—H8B50.9800
C5—H510.9900C8GB—H8B60.9800
C18—H180.9500C4GB—H6GB0.9500
C11—H110.9500N1GB—H1B11.002 (19)
C3—C41.520 (3)N1GB—H1B21.007 (18)
C3—H310.9900C6GB—H4GB0.9500
C3—H320.9900C7GB—H7B10.9800
C4—H420.9900C7GB—H7B20.9800
C4—H410.9900C7GB—H7B30.9800
N1GA—C1GA1.430 (2)
C10—O1—H1112.3 (14)C6GA—C1GA—N1GA118.77 (19)
C16—O2—H2112.5 (15)C2GA—C1GA—N1GA120.56 (17)
C10—C9—C8120.09 (16)C1GA—C2GA—C3GA119.29 (18)
C10—C9—H9120.0C1GA—C2GA—C7GA119.94 (17)
C8—C9—H9120.0C3GA—C2GA—C7GA120.75 (19)
C7—C1—C13107.24 (14)C4GA—C3GA—C2GA119.4 (2)
C7—C1—C6111.11 (14)C4GA—C3GA—C8GA119.81 (19)
C13—C1—C6110.99 (13)C2GA—C3GA—C8GA120.82 (19)
C7—C1—C2109.00 (12)C5GA—C6GA—C1GA119.8 (2)
C13—C1—C2112.39 (13)C5GA—C6GA—H6GA120.1
C6—C1—C2106.13 (14)C1GA—C6GA—H6GA120.1
C3—C2—C1113.84 (13)C2GA—C7GA—H7A1109.5
C3—C2—H21108.8C2GA—C7GA—H7A2109.5
C1—C2—H21108.8H7A1—C7GA—H7A2109.5
C3—C2—H22108.8C2GA—C7GA—H7A3109.5
C1—C2—H22108.8H7A1—C7GA—H7A3109.5
H21—C2—H22107.7H7A2—C7GA—H7A3109.5
C9—C10—O1122.75 (16)C4GA—C5GA—C6GA120.1 (2)
C9—C10—C11119.29 (16)C4GA—C5GA—H5GA120.0
O1—C10—C11117.96 (16)C6GA—C5GA—H5GA120.0
C11—C12—C7122.35 (16)C5GA—C4GA—C3GA120.91 (19)
C11—C12—H12118.8C5GA—C4GA—H4GA119.5
C7—C12—H12118.8C3GA—C4GA—H4GA119.5
C14—C13—C18115.95 (16)C3GA—C8GA—H8A1109.5
C14—C13—C1123.50 (14)C3GA—C8GA—H8A2109.5
C18—C13—C1120.41 (15)H8A1—C8GA—H8A2109.5
C7—C8—C9122.30 (17)C3GA—C8GA—H8A3109.5
C7—C8—H8118.8H8A1—C8GA—H8A3109.5
C9—C8—H8118.8H8A2—C8GA—H8A3109.5
C8—C7—C12116.08 (16)C1GB—C2GB—C3GB119.8 (2)
C8—C7—C1124.31 (16)C1GB—C2GB—C7GB119.4 (2)
C12—C7—C1119.61 (15)C3GB—C2GB—C7GB120.7 (2)
O2—C16—C17122.85 (15)C2GB—C3GB—C4GB119.4 (2)
O2—C16—C15118.03 (15)C2GB—C3GB—C8GB122.3 (2)
C17—C16—C15119.12 (16)C4GB—C3GB—C8GB118.3 (2)
C16—C15—C14119.90 (16)C6GB—C1GB—C2GB119.6 (2)
C16—C15—H15120.1C6GB—C1GB—N1GB118.7 (3)
C14—C15—H15120.1C2GB—C1GB—N1GB121.6 (2)
C16—C17—C18120.21 (15)C4GB—C5GB—C6GB120.4 (2)
C16—C17—H17119.9C4GB—C5GB—H5GB119.8
C18—C17—H17119.9C6GB—C5GB—H5GB119.8
C5—C6—C1112.89 (14)C3GB—C8GB—H8B1109.5
C5—C6—H61109.0C3GB—C8GB—H8B2109.5
C1—C6—H61109.0H8B1—C8GB—H8B2109.5
C5—C6—H62109.0C3GB—C8GB—H8B3109.5
C1—C6—H62109.0H8B1—C8GB—H8B3109.5
H61—C6—H62107.8H8B2—C8GB—H8B3109.5
C15—C14—C13122.51 (15)C3GB—C8GB—H8B4109.5
C15—C14—H14118.7H8B1—C8GB—H8B4141.1
C13—C14—H14118.7H8B2—C8GB—H8B456.3
C6—C5—C4110.84 (14)H8B3—C8GB—H8B456.3
C6—C5—H52109.5C3GB—C8GB—H8B5109.5
C4—C5—H52109.5H8B1—C8GB—H8B556.3
C6—C5—H51109.5H8B2—C8GB—H8B5141.1
C4—C5—H51109.5H8B3—C8GB—H8B556.3
H52—C5—H51108.1H8B4—C8GB—H8B5109.5
C17—C18—C13122.31 (16)C3GB—C8GB—H8B6109.5
C17—C18—H18118.8H8B1—C8GB—H8B656.3
C13—C18—H18118.8H8B2—C8GB—H8B656.3
C12—C11—C10119.87 (17)H8B3—C8GB—H8B6141.1
C12—C11—H11120.1H8B4—C8GB—H8B6109.5
C10—C11—H11120.1H8B5—C8GB—H8B6109.5
C4—C3—C2111.08 (15)C5GB—C4GB—C3GB120.3 (2)
C4—C3—H31109.4C5GB—C4GB—H6GB119.8
C2—C3—H31109.4C3GB—C4GB—H6GB119.8
C4—C3—H32109.4C1GB—N1GB—H1B1117 (3)
C2—C3—H32109.4C1GB—N1GB—H1B2108 (2)
H31—C3—H32108.0H1B1—N1GB—H1B2106 (3)
C3—C4—C5110.84 (16)C5GB—C6GB—C1GB120.3 (2)
C3—C4—H42109.5C5GB—C6GB—H4GB119.8
C5—C4—H42109.5C1GB—C6GB—H4GB119.8
C3—C4—H41109.5C2GB—C7GB—H7B1109.5
C5—C4—H41109.5C2GB—C7GB—H7B2109.5
H42—C4—H41108.1H7B1—C7GB—H7B2109.5
C1GA—N1GA—H1A1109.5 (14)C2GB—C7GB—H7B3109.5
C1GA—N1GA—H1A2112.2 (13)H7B1—C7GB—H7B3109.5
H1A1—N1GA—H1A2113.3 (19)H7B2—C7GB—H7B3109.5
C6GA—C1GA—C2GA120.57 (18)
C7—C1—C2—C3175.17 (15)C1—C13—C18—C17176.07 (16)
C13—C1—C2—C366.1 (2)C7—C12—C11—C100.0 (3)
C6—C1—C2—C355.42 (18)C9—C10—C11—C120.9 (3)
C8—C9—C10—O1179.72 (15)O1—C10—C11—C12179.52 (16)
C8—C9—C10—C110.7 (3)C1—C2—C3—C455.9 (2)
C7—C1—C13—C14101.73 (19)C2—C3—C4—C553.96 (19)
C6—C1—C13—C14136.73 (17)C6—C5—C4—C355.8 (2)
C2—C1—C13—C1418.0 (2)C6GA—C1GA—C2GA—C3GA0.6 (2)
C7—C1—C13—C1873.86 (19)N1GA—C1GA—C2GA—C3GA176.98 (15)
C6—C1—C13—C1847.7 (2)C6GA—C1GA—C2GA—C7GA179.10 (16)
C2—C1—C13—C18166.36 (16)N1GA—C1GA—C2GA—C7GA4.5 (2)
C10—C9—C8—C70.4 (3)C1GA—C2GA—C3GA—C4GA0.9 (2)
C9—C8—C7—C121.3 (2)C7GA—C2GA—C3GA—C4GA179.38 (16)
C9—C8—C7—C1178.36 (16)C1GA—C2GA—C3GA—C8GA178.37 (17)
C11—C12—C7—C81.1 (3)C7GA—C2GA—C3GA—C8GA0.1 (3)
C11—C12—C7—C1178.56 (16)C2GA—C1GA—C6GA—C5GA0.0 (3)
C13—C1—C7—C8122.90 (17)N1GA—C1GA—C6GA—C5GA176.45 (15)
C6—C1—C7—C81.4 (2)C1GA—C6GA—C5GA—C4GA0.3 (3)
C2—C1—C7—C8115.18 (18)C6GA—C5GA—C4GA—C3GA0.0 (3)
C13—C1—C7—C1256.76 (19)C2GA—C3GA—C4GA—C5GA0.6 (3)
C6—C1—C7—C12178.22 (15)C8GA—C3GA—C4GA—C5GA178.67 (18)
C2—C1—C7—C1265.2 (2)C1GB—C2GB—C3GB—C4GB1.7 (3)
O2—C16—C15—C14179.59 (16)C7GB—C2GB—C3GB—C4GB175.0 (2)
C17—C16—C15—C140.3 (3)C1GB—C2GB—C3GB—C8GB179.2 (2)
O2—C16—C17—C18179.38 (17)C7GB—C2GB—C3GB—C8GB2.5 (3)
C15—C16—C17—C180.5 (3)C3GB—C2GB—C1GB—C6GB3.0 (3)
C7—C1—C6—C5175.28 (14)C7GB—C2GB—C1GB—C6GB173.8 (2)
C13—C1—C6—C565.47 (18)C3GB—C2GB—C1GB—N1GB175.7 (2)
C2—C1—C6—C556.92 (17)C7GB—C2GB—C1GB—N1GB7.5 (3)
C16—C15—C14—C130.0 (3)C6GB—C5GB—C4GB—C3GB2.3 (4)
C18—C13—C14—C150.1 (3)C2GB—C3GB—C4GB—C5GB1.0 (3)
C1—C13—C14—C15175.71 (16)C8GB—C3GB—C4GB—C5GB176.7 (2)
C1—C6—C5—C459.3 (2)C4GB—C5GB—C6GB—C1GB1.0 (4)
C16—C17—C18—C130.4 (3)C2GB—C1GB—C6GB—C5GB1.7 (4)
C14—C13—C18—C170.1 (3)N1GB—C1GB—C6GB—C5GB177.1 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.98 (1)1.73 (1)2.7071 (17)178 (2)
O2—H2···N1GAii0.98 (1)1.76 (1)2.7341 (19)172 (2)
N1GA—H1A2···O10.96 (1)2.10 (1)3.033 (2)163 (2)
N1GA—H1A1···N1GB0.94 (1)2.98 (1)3.789 (3)146 (2)
Symmetry codes: (i) x, y+1, z; (ii) x1, y1, z.
(dc34x0.5) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 3,4-xylidine, water top
Crystal data top
C18H20O2/0.5(C8H11N)/H2OZ = 4
Mr = 346.95F(000) = 748
Triclinic, P1Dx = 1.230 Mg m3
Dm = N/A Mg m3
Dm measured by not measured
a = 10.8979 (5) ÅMelting point: 359.35K, 392.75K and 403.35K for guests release onset temp. and 463.15K for host melting K
b = 12.5017 (7) ÅMo Kα radiation, λ = 0.71069 Å
c = 15.1701 (7) ŵ = 0.08 mm1
α = 106.510 (4)°T = 173 K
β = 99.895 (3)°Prism, colourless
γ = 102.559 (2)°0.30 × 0.30 × 0.20 mm
V = 1872.93 (16) Å3
Data collection top
Nonius Kappa CCD
diffractometer
3621 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.022
Graphite monochromatorθmax = 25.4°, θmin = 2.6°
φ scans and ω scansh = 1311
10118 measured reflectionsk = 1115
6720 independent reflectionsl = 1815
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.065H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.149 w = 1/[σ2(Fo2) + (0.0322P)2 + 2.1868P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max < 0.001
6720 reflectionsΔρmax = 0.38 e Å3
497 parametersΔρmin = 0.36 e Å3
22 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0027 (6)
Special details top

Experimental. Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40 mm; combination of φ and ω scans of 1°, 80 s per °, 2 iterations.

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*/Ueq
O1Y1.1341 (2)0.1345 (2)0.17979 (15)0.0331 (6)
O2Y0.2774 (2)0.01417 (19)0.13813 (14)0.0324 (6)
O1X0.2661 (2)0.47495 (19)0.14053 (14)0.0338 (6)
C1Y0.7649 (3)0.0817 (2)0.40287 (19)0.0187 (7)
C1X0.7598 (3)0.5796 (2)0.39954 (19)0.0179 (6)
C13Y0.6303 (3)0.0577 (2)0.33582 (18)0.0179 (7)
C7X0.6247 (3)0.5543 (2)0.33376 (18)0.0182 (7)
C8X0.5668 (3)0.4450 (2)0.26438 (19)0.0216 (7)
H8X0.61040.38650.26070.026*
C10X0.3837 (3)0.5035 (3)0.20438 (19)0.0221 (7)
C11X0.4390 (3)0.6137 (3)0.2710 (2)0.0247 (7)
H11X0.39610.67260.27300.030*
C10Y1.0443 (3)0.1216 (3)0.2325 (2)0.0227 (7)
C17Y0.4481 (3)0.1202 (3)0.27271 (19)0.0226 (7)
H17Y0.40590.17950.27530.027*
C9X0.4482 (3)0.4188 (3)0.20090 (19)0.0244 (7)
H9X0.41110.34320.15520.029*
C6Y0.8004 (3)0.1951 (2)0.48859 (19)0.0211 (7)
H6Y20.89180.21160.52330.025*
H6Y10.79420.26010.46470.025*
C8Y0.9482 (3)0.0229 (2)0.32947 (19)0.0214 (7)
H8Y0.94450.03560.35820.026*
C17X1.0334 (3)0.5357 (3)0.2726 (2)0.0251 (7)
H17X1.08980.48740.26520.030*
C14X0.8680 (3)0.6740 (2)0.2944 (2)0.0230 (7)
H14X0.81090.72180.30090.028*
C7Y0.8652 (3)0.0929 (2)0.34328 (18)0.0176 (6)
C9Y1.0365 (3)0.0365 (3)0.2746 (2)0.0259 (7)
H9Y1.09170.01280.26600.031*
C16Y0.3936 (3)0.0114 (3)0.20444 (19)0.0226 (7)
C16X1.0389 (3)0.6192 (3)0.2290 (2)0.0221 (7)
C15Y0.4564 (3)0.0741 (3)0.20081 (19)0.0231 (7)
H15Y0.41960.14890.15380.028*
C14Y0.5723 (3)0.0506 (2)0.26543 (19)0.0209 (7)
H14Y0.61430.11030.26200.025*
C5Y0.7143 (3)0.1911 (3)0.5579 (2)0.0246 (7)
H5Y10.74640.26440.61270.029*
H5Y20.62450.18490.52590.029*
C12Y0.8748 (3)0.1774 (3)0.29940 (19)0.0229 (7)
H12Y0.81900.22630.30710.028*
C2Y0.7673 (3)0.0178 (2)0.44374 (19)0.0209 (7)
H2Y10.74110.09260.39070.025*
H2Y20.85720.00630.47890.025*
C18X0.9448 (3)0.5227 (3)0.3276 (2)0.0241 (7)
H18X0.94220.46540.35750.029*
C2X0.7653 (3)0.4819 (2)0.44222 (19)0.0215 (7)
H2X10.74010.40650.39000.026*
H2X20.85570.49530.47750.026*
C3X0.6761 (3)0.4754 (3)0.5091 (2)0.0254 (7)
H3X20.58510.45830.47340.031*
H3X10.68260.41110.53400.031*
C12X0.5578 (3)0.6376 (3)0.3348 (2)0.0223 (7)
H12X0.59450.71320.38060.027*
C6X0.7956 (3)0.6937 (2)0.48495 (19)0.0209 (7)
H6X10.88720.71050.51950.025*
H6X20.78880.75830.46070.025*
C13X0.8599 (3)0.5912 (2)0.33983 (19)0.0190 (7)
C11Y0.9629 (3)0.1927 (3)0.2449 (2)0.0228 (7)
H11Y0.96740.25150.21630.027*
C3Y0.6771 (3)0.0248 (3)0.5104 (2)0.0268 (7)
H3Y20.58630.04150.47460.032*
H3Y10.68320.08920.53510.032*
C18Y0.5650 (3)0.1422 (2)0.33750 (19)0.0204 (7)
H18Y0.60160.21700.38440.024*
C15X0.9562 (3)0.6892 (3)0.2403 (2)0.0248 (7)
H15X0.95990.74730.21100.030*
C5X0.7098 (3)0.6897 (3)0.55464 (19)0.0236 (7)
H5X20.74080.76370.60870.028*
H5X10.61950.68160.52250.028*
C4X0.7120 (3)0.5888 (3)0.5916 (2)0.0266 (7)
H4X10.79980.60210.63120.032*
H4X20.64970.58390.63170.032*
C4Y0.7135 (3)0.0889 (3)0.5931 (2)0.0303 (8)
H4Y20.65050.08430.63270.036*
H4Y10.80060.10100.63320.036*
C4G0.6040 (4)0.3300 (3)0.0191 (3)0.0491 (11)
C2G0.4564 (4)0.1540 (3)0.0175 (3)0.0491 (11)
H2G0.44030.08740.03680.059*
N1G0.2260 (3)0.0939 (3)0.0650 (2)0.0654 (10)
C3G0.5808 (4)0.2316 (3)0.0484 (2)0.0442 (10)
C5G0.5015 (5)0.3446 (3)0.0394 (3)0.0544 (11)
H5G0.51770.41050.05970.065*
C6G0.3767 (5)0.2697 (3)0.0707 (3)0.0594 (13)
H6G0.30870.28340.11040.071*
C1G0.3564 (4)0.1720 (3)0.0404 (3)0.0459 (10)
C7G0.6829 (4)0.2078 (4)0.1057 (3)0.0627 (12)
H7G10.64630.14350.12690.094*
H7G20.72830.27730.16110.094*
H7G30.74430.18640.06840.094*
C8G0.7396 (4)0.4149 (3)0.0554 (3)0.0689 (14)
H8G10.74220.47830.02920.103*
H8G20.80270.37410.03540.103*
H8G30.76110.44680.12480.103*
O2X1.1278 (2)0.6313 (2)0.17562 (15)0.0331 (6)
O2W0.1109 (2)0.2480 (2)0.05724 (18)0.0510 (7)
O1W0.1062 (2)0.7659 (3)0.0720 (2)0.0710 (10)
H1X0.226 (3)0.539 (2)0.154 (3)0.069 (13)*
H2Y0.229 (4)0.042 (3)0.153 (3)0.103 (17)*
H1Y1.122 (4)0.186 (3)0.143 (2)0.091 (15)*
H2X1.113 (4)0.676 (3)0.135 (3)0.089 (15)*
H1W20.033 (3)0.758 (4)0.025 (3)0.107*
H2W10.155 (4)0.328 (2)0.097 (3)0.107*
H1G10.202 (3)0.063 (3)0.1348 (17)0.107*
H1G20.257 (3)0.032 (3)0.042 (3)0.107*
H2W20.160 (4)0.203 (3)0.020 (3)0.107*
H1W10.165 (4)0.840 (2)0.090 (3)0.107*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O1Y0.0298 (12)0.0462 (15)0.0425 (14)0.0216 (11)0.0224 (11)0.0274 (12)
O2Y0.0238 (12)0.0381 (15)0.0266 (12)0.0111 (11)0.0059 (9)0.0034 (10)
O1X0.0292 (13)0.0374 (15)0.0296 (12)0.0181 (11)0.0037 (10)0.0032 (11)
C1Y0.0200 (15)0.0168 (16)0.0203 (15)0.0054 (13)0.0040 (12)0.0081 (13)
C1X0.0183 (15)0.0151 (16)0.0212 (15)0.0052 (12)0.0052 (12)0.0067 (13)
C13Y0.0177 (15)0.0202 (17)0.0180 (15)0.0054 (13)0.0078 (12)0.0078 (13)
C7X0.0190 (15)0.0195 (17)0.0181 (15)0.0064 (13)0.0053 (12)0.0083 (13)
C8X0.0243 (16)0.0185 (17)0.0238 (16)0.0114 (13)0.0067 (13)0.0055 (13)
C10X0.0172 (16)0.0319 (19)0.0179 (16)0.0096 (14)0.0031 (12)0.0081 (14)
C11X0.0262 (17)0.0255 (19)0.0269 (17)0.0151 (14)0.0060 (13)0.0099 (14)
C10Y0.0161 (16)0.0269 (19)0.0251 (17)0.0050 (14)0.0055 (13)0.0090 (14)
C17Y0.0255 (17)0.0233 (18)0.0239 (16)0.0142 (14)0.0077 (13)0.0090 (14)
C9X0.0242 (17)0.0246 (18)0.0209 (16)0.0081 (14)0.0027 (13)0.0032 (14)
C6Y0.0221 (16)0.0176 (17)0.0218 (16)0.0041 (13)0.0023 (12)0.0069 (13)
C8Y0.0235 (16)0.0206 (17)0.0230 (16)0.0087 (13)0.0049 (13)0.0104 (13)
C17X0.0231 (17)0.0263 (19)0.0325 (18)0.0153 (14)0.0089 (14)0.0122 (15)
C14X0.0219 (16)0.0204 (17)0.0319 (17)0.0112 (13)0.0087 (13)0.0114 (14)
C7Y0.0156 (15)0.0171 (16)0.0187 (15)0.0054 (12)0.0013 (12)0.0049 (13)
C9Y0.0253 (17)0.0286 (19)0.0310 (18)0.0152 (14)0.0092 (14)0.0139 (15)
C16Y0.0197 (16)0.0310 (19)0.0175 (15)0.0090 (14)0.0037 (12)0.0079 (14)
C16X0.0172 (16)0.0250 (18)0.0264 (17)0.0066 (14)0.0073 (13)0.0105 (14)
C15Y0.0280 (17)0.0193 (17)0.0191 (16)0.0090 (14)0.0072 (13)0.0005 (13)
C14Y0.0217 (16)0.0193 (17)0.0226 (16)0.0111 (13)0.0049 (13)0.0048 (13)
C5Y0.0256 (17)0.0242 (18)0.0210 (16)0.0069 (14)0.0036 (13)0.0047 (14)
C12Y0.0218 (16)0.0218 (18)0.0285 (17)0.0099 (13)0.0081 (13)0.0095 (14)
C2Y0.0224 (16)0.0169 (17)0.0260 (16)0.0081 (13)0.0048 (13)0.0101 (13)
C18X0.0221 (16)0.0254 (18)0.0303 (17)0.0093 (14)0.0076 (13)0.0153 (15)
C2X0.0217 (16)0.0204 (17)0.0223 (16)0.0070 (13)0.0019 (12)0.0080 (13)
C3X0.0290 (17)0.0223 (18)0.0299 (17)0.0074 (14)0.0095 (14)0.0147 (14)
C12X0.0239 (16)0.0175 (17)0.0246 (16)0.0068 (13)0.0068 (13)0.0047 (13)
C6X0.0196 (15)0.0186 (17)0.0238 (16)0.0045 (13)0.0040 (12)0.0074 (13)
C13X0.0167 (15)0.0179 (17)0.0197 (15)0.0020 (13)0.0025 (12)0.0057 (13)
C11Y0.0232 (16)0.0231 (18)0.0269 (17)0.0089 (14)0.0070 (13)0.0132 (14)
C3Y0.0293 (18)0.0265 (19)0.0335 (18)0.0118 (15)0.0112 (14)0.0184 (15)
C18Y0.0241 (16)0.0143 (16)0.0224 (16)0.0067 (13)0.0039 (13)0.0056 (13)
C15X0.0277 (17)0.0201 (18)0.0318 (17)0.0085 (14)0.0107 (14)0.0132 (14)
C5X0.0272 (17)0.0221 (18)0.0200 (16)0.0080 (14)0.0059 (13)0.0041 (13)
C4X0.0290 (17)0.031 (2)0.0238 (16)0.0098 (15)0.0079 (13)0.0136 (15)
C4Y0.0351 (19)0.036 (2)0.0275 (17)0.0144 (16)0.0116 (14)0.0159 (16)
C4G0.081 (3)0.0201 (19)0.043 (2)0.0025 (19)0.047 (2)0.0039 (17)
C2G0.072 (3)0.022 (2)0.051 (2)0.0010 (19)0.046 (2)0.0004 (17)
N1G0.059 (2)0.050 (2)0.059 (2)0.0064 (18)0.0147 (18)0.0070 (18)
C3G0.063 (3)0.044 (2)0.034 (2)0.027 (2)0.0290 (18)0.0068 (17)
C5G0.100 (4)0.031 (2)0.047 (2)0.027 (2)0.042 (2)0.0139 (18)
C6G0.095 (3)0.021 (2)0.059 (3)0.003 (2)0.057 (2)0.0049 (18)
C1G0.051 (2)0.039 (2)0.039 (2)0.0127 (19)0.0185 (18)0.0047 (17)
C7G0.066 (3)0.076 (3)0.053 (3)0.032 (2)0.020 (2)0.019 (2)
C8G0.086 (3)0.045 (3)0.047 (2)0.021 (2)0.040 (2)0.0107 (19)
O2X0.0328 (13)0.0424 (15)0.0436 (14)0.0201 (11)0.0228 (11)0.0287 (12)
O2W0.0360 (15)0.0557 (18)0.0597 (18)0.0026 (13)0.0003 (12)0.0316 (14)
O1W0.0412 (17)0.064 (2)0.100 (2)0.0128 (14)0.0166 (15)0.0573 (19)
Geometric parameters (Å, º) top
O1Y—C10Y1.376 (3)C12Y—H12Y0.9500
O1Y—H1Y0.977 (15)C2Y—C3Y1.533 (4)
O2Y—C16Y1.387 (3)C2Y—H2Y10.9900
O2Y—H2Y0.964 (14)C2Y—H2Y20.9900
O1X—C10X1.374 (3)C18X—C13X1.392 (4)
O1X—H1X0.984 (14)C18X—H18X0.9500
C1Y—C7Y1.542 (4)C2X—C3X1.527 (4)
C1Y—C2Y1.543 (4)C2X—H2X10.9900
C1Y—C6Y1.547 (4)C2X—H2X20.9900
C1Y—C13Y1.548 (4)C3X—C4X1.520 (4)
C1X—C13X1.541 (4)C3X—H3X20.9900
C1X—C7X1.542 (4)C3X—H3X10.9900
C1X—C2X1.544 (4)C12X—H12X0.9500
C1X—C6X1.549 (4)C6X—C5X1.531 (4)
C13Y—C18Y1.393 (4)C6X—H6X10.9900
C13Y—C14Y1.395 (4)C6X—H6X20.9900
C7X—C12X1.393 (4)C11Y—H11Y0.9500
C7X—C8X1.397 (4)C3Y—C4Y1.524 (4)
C8X—C9X1.383 (4)C3Y—H3Y20.9900
C8X—H8X0.9500C3Y—H3Y10.9900
C10X—C11X1.386 (4)C18Y—H18Y0.9500
C10X—C9X1.386 (4)C15X—H15X0.9500
C11X—C12X1.393 (4)C5X—C4X1.522 (4)
C11X—H11X0.9500C5X—H5X20.9900
C10Y—C9Y1.383 (4)C5X—H5X10.9900
C10Y—C11Y1.385 (4)C4X—H4X10.9900
C17Y—C16Y1.383 (4)C4X—H4X20.9900
C17Y—C18Y1.389 (4)C4Y—H4Y20.9900
C17Y—H17Y0.9500C4Y—H4Y10.9900
C9X—H9X0.9500C4G—C5G1.382 (6)
C6Y—C5Y1.529 (4)C4G—C3G1.411 (5)
C6Y—H6Y20.9900C4G—C8G1.522 (5)
C6Y—H6Y10.9900C2G—C1G1.378 (5)
C8Y—C9Y1.390 (4)C2G—C3G1.397 (5)
C8Y—C7Y1.391 (4)C2G—H2G0.9500
C8Y—H8Y0.9500N1G—C1G1.456 (5)
C17X—C16X1.381 (4)N1G—H1G10.98 (2)
C17X—C18X1.393 (4)N1G—H1G21.03 (2)
C17X—H17X0.9500C3G—C7G1.429 (5)
C14X—C15X1.384 (4)C5G—C6G1.387 (6)
C14X—C13X1.393 (4)C5G—H5G0.9500
C14X—H14X0.9500C6G—C1G1.410 (5)
C7Y—C12Y1.394 (4)C6G—H6G0.9500
C9Y—H9Y0.9500C7G—H7G10.9800
C16Y—C15Y1.382 (4)C7G—H7G20.9800
C16X—O2X1.376 (3)C7G—H7G30.9800
C16X—C15X1.386 (4)C8G—H8G10.9800
C15Y—C14Y1.375 (4)C8G—H8G20.9800
C15Y—H15Y0.9500C8G—H8G30.9800
C14Y—H14Y0.9500O2X—H2X0.959 (14)
C5Y—C4Y1.517 (4)O2W—H2W10.971 (19)
C5Y—H5Y10.9900O2W—H2W20.98 (2)
C5Y—H5Y20.9900O1W—H1W20.94 (2)
C12Y—C11Y1.387 (4)O1W—H1W10.94 (2)
C10Y—O1Y—H1Y113 (2)C1X—C2X—H2X1109.1
C16Y—O2Y—H2Y115 (3)C3X—C2X—H2X2109.1
C10X—O1X—H1X111 (2)C1X—C2X—H2X2109.1
C7Y—C1Y—C2Y111.4 (2)H2X1—C2X—H2X2107.8
C7Y—C1Y—C6Y108.9 (2)C4X—C3X—C2X111.2 (2)
C2Y—C1Y—C6Y106.8 (2)C4X—C3X—H3X2109.4
C7Y—C1Y—C13Y106.6 (2)C2X—C3X—H3X2109.4
C2Y—C1Y—C13Y110.5 (2)C4X—C3X—H3X1109.4
C6Y—C1Y—C13Y112.7 (2)C2X—C3X—H3X1109.4
C13X—C1X—C7X107.3 (2)H3X2—C3X—H3X1108.0
C13X—C1X—C2X111.3 (2)C11X—C12X—C7X122.2 (3)
C7X—C1X—C2X110.9 (2)C11X—C12X—H12X118.9
C13X—C1X—C6X108.6 (2)C7X—C12X—H12X118.9
C7X—C1X—C6X112.7 (2)C5X—C6X—C1X113.8 (2)
C2X—C1X—C6X106.1 (2)C5X—C6X—H6X1108.8
C18Y—C13Y—C14Y116.6 (2)C1X—C6X—H6X1108.8
C18Y—C13Y—C1Y123.2 (2)C5X—C6X—H6X2108.8
C14Y—C13Y—C1Y120.2 (2)C1X—C6X—H6X2108.8
C12X—C7X—C8X116.4 (2)H6X1—C6X—H6X2107.7
C12X—C7X—C1X123.5 (2)C18X—C13X—C14X116.6 (3)
C8X—C7X—C1X119.9 (2)C18X—C13X—C1X123.8 (2)
C9X—C8X—C7X122.5 (3)C14X—C13X—C1X119.6 (3)
C9X—C8X—H8X118.8C10Y—C11Y—C12Y119.4 (3)
C7X—C8X—H8X118.8C10Y—C11Y—H11Y120.3
O1X—C10X—C11X121.9 (3)C12Y—C11Y—H11Y120.3
O1X—C10X—C9X118.3 (3)C4Y—C3Y—C2Y110.9 (2)
C11X—C10X—C9X119.7 (3)C4Y—C3Y—H3Y2109.5
C10X—C11X—C12X119.6 (3)C2Y—C3Y—H3Y2109.5
C10X—C11X—H11X120.2C4Y—C3Y—H3Y1109.5
C12X—C11X—H11X120.2C2Y—C3Y—H3Y1109.5
O1Y—C10Y—C9Y119.1 (3)H3Y2—C3Y—H3Y1108.1
O1Y—C10Y—C11Y121.4 (3)C17Y—C18Y—C13Y122.0 (3)
C9Y—C10Y—C11Y119.5 (3)C17Y—C18Y—H18Y119.0
C16Y—C17Y—C18Y119.6 (3)C13Y—C18Y—H18Y119.0
C16Y—C17Y—H17Y120.2C14X—C15X—C16X119.6 (3)
C18Y—C17Y—H17Y120.2C14X—C15X—H15X120.2
C8X—C9X—C10X119.6 (3)C16X—C15X—H15X120.2
C8X—C9X—H9X120.2C4X—C5X—C6X111.4 (2)
C10X—C9X—H9X120.2C4X—C5X—H5X2109.4
C5Y—C6Y—C1Y114.0 (2)C6X—C5X—H5X2109.4
C5Y—C6Y—H6Y2108.8C4X—C5X—H5X1109.4
C1Y—C6Y—H6Y2108.8C6X—C5X—H5X1109.4
C5Y—C6Y—H6Y1108.8H5X2—C5X—H5X1108.0
C1Y—C6Y—H6Y1108.8C3X—C4X—C5X110.2 (2)
H6Y2—C6Y—H6Y1107.7C3X—C4X—H4X1109.6
C9Y—C8Y—C7Y121.6 (3)C5X—C4X—H4X1109.6
C9Y—C8Y—H8Y119.2C3X—C4X—H4X2109.6
C7Y—C8Y—H8Y119.2C5X—C4X—H4X2109.6
C16X—C17X—C18X119.7 (3)H4X1—C4X—H4X2108.1
C16X—C17X—H17X120.1C5Y—C4Y—C3Y111.1 (2)
C18X—C17X—H17X120.1C5Y—C4Y—H4Y2109.4
C15X—C14X—C13X122.4 (3)C3Y—C4Y—H4Y2109.4
C15X—C14X—H14X118.8C5Y—C4Y—H4Y1109.4
C13X—C14X—H14X118.8C3Y—C4Y—H4Y1109.4
C8Y—C7Y—C12Y116.7 (3)H4Y2—C4Y—H4Y1108.0
C8Y—C7Y—C1Y124.0 (2)C5G—C4G—C3G117.9 (4)
C12Y—C7Y—C1Y119.2 (3)C5G—C4G—C8G124.0 (4)
C10Y—C9Y—C8Y120.3 (3)C3G—C4G—C8G118.1 (4)
C10Y—C9Y—H9Y119.9C1G—C2G—C3G121.4 (4)
C8Y—C9Y—H9Y119.9C1G—C2G—H2G119.3
C15Y—C16Y—C17Y119.8 (3)C3G—C2G—H2G119.3
C15Y—C16Y—O2Y118.7 (3)C1G—N1G—H1G1105 (2)
C17Y—C16Y—O2Y121.5 (3)C1G—N1G—H1G294.1 (19)
O2X—C16X—C17X118.9 (3)H1G1—N1G—H1G2107 (3)
O2X—C16X—C15X121.4 (3)C2G—C3G—C4G119.0 (4)
C17X—C16X—C15X119.7 (3)C2G—C3G—C7G119.7 (4)
C14Y—C15Y—C16Y119.8 (3)C4G—C3G—C7G121.3 (4)
C14Y—C15Y—H15Y120.1C4G—C5G—C6G124.5 (4)
C16Y—C15Y—H15Y120.1C4G—C5G—H5G117.8
C15Y—C14Y—C13Y122.3 (3)C6G—C5G—H5G117.8
C15Y—C14Y—H14Y118.8C5G—C6G—C1G116.3 (4)
C13Y—C14Y—H14Y118.8C5G—C6G—H6G121.8
C4Y—C5Y—C6Y111.5 (2)C1G—C6G—H6G121.8
C4Y—C5Y—H5Y1109.3C2G—C1G—C6G120.9 (4)
C6Y—C5Y—H5Y1109.3C2G—C1G—N1G119.6 (4)
C4Y—C5Y—H5Y2109.3C6G—C1G—N1G119.4 (4)
C6Y—C5Y—H5Y2109.3C3G—C7G—H7G1109.5
H5Y1—C5Y—H5Y2108.0C3G—C7G—H7G2109.5
C11Y—C12Y—C7Y122.5 (3)H7G1—C7G—H7G2109.5
C11Y—C12Y—H12Y118.8C3G—C7G—H7G3109.5
C7Y—C12Y—H12Y118.8H7G1—C7G—H7G3109.5
C3Y—C2Y—C1Y112.8 (2)H7G2—C7G—H7G3109.5
C3Y—C2Y—H2Y1109.0C4G—C8G—H8G1109.5
C1Y—C2Y—H2Y1109.0C4G—C8G—H8G2109.5
C3Y—C2Y—H2Y2109.0H8G1—C8G—H8G2109.5
C1Y—C2Y—H2Y2109.0C4G—C8G—H8G3109.5
H2Y1—C2Y—H2Y2107.8H8G1—C8G—H8G3109.5
C13X—C18X—C17X121.9 (3)H8G2—C8G—H8G3109.5
C13X—C18X—H18X119.0C16X—O2X—H2X115 (3)
C17X—C18X—H18X119.0H2W1—O2W—H2W2118 (3)
C3X—C2X—C1X112.6 (2)H1W2—O1W—H1W1110 (4)
C3X—C2X—H2X1109.1
C7Y—C1Y—C13Y—C18Y103.1 (3)C13X—C1X—C2X—C3X174.8 (2)
C2Y—C1Y—C13Y—C18Y135.7 (3)C7X—C1X—C2X—C3X65.8 (3)
C6Y—C1Y—C13Y—C18Y16.3 (4)C6X—C1X—C2X—C3X56.9 (3)
C7Y—C1Y—C13Y—C14Y72.7 (3)C1X—C2X—C3X—C4X59.6 (3)
C2Y—C1Y—C13Y—C14Y48.5 (3)C10X—C11X—C12X—C7X0.6 (4)
C6Y—C1Y—C13Y—C14Y167.9 (2)C8X—C7X—C12X—C11X0.5 (4)
C13X—C1X—C7X—C12X102.8 (3)C1X—C7X—C12X—C11X176.4 (3)
C2X—C1X—C7X—C12X135.5 (3)C13X—C1X—C6X—C5X175.3 (2)
C6X—C1X—C7X—C12X16.7 (4)C7X—C1X—C6X—C5X66.0 (3)
C13X—C1X—C7X—C8X73.0 (3)C2X—C1X—C6X—C5X55.6 (3)
C2X—C1X—C7X—C8X48.8 (3)C17X—C18X—C13X—C14X0.1 (4)
C6X—C1X—C7X—C8X167.5 (2)C17X—C18X—C13X—C1X179.7 (3)
C12X—C7X—C8X—C9X1.3 (4)C15X—C14X—C13X—C18X0.5 (4)
C1X—C7X—C8X—C9X177.3 (3)C15X—C14X—C13X—C1X179.6 (3)
O1X—C10X—C11X—C12X179.2 (3)C7X—C1X—C13X—C18X122.3 (3)
C9X—C10X—C11X—C12X1.1 (4)C2X—C1X—C13X—C18X0.7 (4)
C7X—C8X—C9X—C10X0.8 (4)C6X—C1X—C13X—C18X115.7 (3)
O1X—C10X—C9X—C8X179.9 (3)C7X—C1X—C13X—C14X57.6 (3)
C11X—C10X—C9X—C8X0.4 (4)C2X—C1X—C13X—C14X179.1 (2)
C7Y—C1Y—C6Y—C5Y175.3 (2)C6X—C1X—C13X—C14X64.5 (3)
C2Y—C1Y—C6Y—C5Y54.9 (3)O1Y—C10Y—C11Y—C12Y179.3 (3)
C13Y—C1Y—C6Y—C5Y66.6 (3)C9Y—C10Y—C11Y—C12Y0.0 (4)
C9Y—C8Y—C7Y—C12Y0.0 (4)C7Y—C12Y—C11Y—C10Y0.4 (4)
C9Y—C8Y—C7Y—C1Y179.7 (3)C1Y—C2Y—C3Y—C4Y58.4 (3)
C2Y—C1Y—C7Y—C8Y0.8 (4)C16Y—C17Y—C18Y—C13Y0.3 (4)
C6Y—C1Y—C7Y—C8Y116.7 (3)C14Y—C13Y—C18Y—C17Y0.1 (4)
C13Y—C1Y—C7Y—C8Y121.4 (3)C1Y—C13Y—C18Y—C17Y176.0 (2)
C2Y—C1Y—C7Y—C12Y178.9 (2)C13X—C14X—C15X—C16X0.9 (4)
C6Y—C1Y—C7Y—C12Y63.6 (3)O2X—C16X—C15X—C14X179.9 (3)
C13Y—C1Y—C7Y—C12Y58.3 (3)C17X—C16X—C15X—C14X0.6 (4)
O1Y—C10Y—C9Y—C8Y178.9 (3)C1X—C6X—C5X—C4X56.3 (3)
C11Y—C10Y—C9Y—C8Y0.4 (4)C2X—C3X—C4X—C5X55.9 (3)
C7Y—C8Y—C9Y—C10Y0.4 (4)C6X—C5X—C4X—C3X54.1 (3)
C18Y—C17Y—C16Y—C15Y0.5 (4)C6Y—C5Y—C4Y—C3Y53.6 (3)
C18Y—C17Y—C16Y—O2Y179.7 (3)C2Y—C3Y—C4Y—C5Y55.2 (3)
C18X—C17X—C16X—O2X179.5 (3)C1G—C2G—C3G—C4G0.2 (5)
C18X—C17X—C16X—C15X0.0 (4)C1G—C2G—C3G—C7G177.9 (3)
C17Y—C16Y—C15Y—C14Y0.4 (4)C5G—C4G—C3G—C2G0.3 (5)
O2Y—C16Y—C15Y—C14Y179.6 (3)C8G—C4G—C3G—C2G178.7 (3)
C16Y—C15Y—C14Y—C13Y0.0 (4)C5G—C4G—C3G—C7G177.4 (3)
C18Y—C13Y—C14Y—C15Y0.2 (4)C8G—C4G—C3G—C7G3.7 (5)
C1Y—C13Y—C14Y—C15Y176.3 (3)C3G—C4G—C5G—C6G0.8 (5)
C1Y—C6Y—C5Y—C4Y55.3 (3)C8G—C4G—C5G—C6G178.1 (3)
C8Y—C7Y—C12Y—C11Y0.4 (4)C4G—C5G—C6G—C1G0.8 (5)
C1Y—C7Y—C12Y—C11Y179.9 (2)C3G—C2G—C1G—C6G0.2 (5)
C7Y—C1Y—C2Y—C3Y175.1 (2)C3G—C2G—C1G—N1G175.4 (3)
C6Y—C1Y—C2Y—C3Y56.2 (3)C5G—C6G—C1G—C2G0.3 (5)
C13Y—C1Y—C2Y—C3Y66.6 (3)C5G—C6G—C1G—N1G175.8 (3)
C16X—C17X—C18X—C13X0.4 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1Y—H1Y···O2Wi0.98 (2)1.70 (2)2.651 (3)165 (4)
O2Y—H2Y···O1Yii0.96 (1)1.73 (1)2.688 (3)176 (4)
O1X—H1X···O2Xii0.98 (1)1.74 (1)2.709 (3)168 (3)
O2X—H2X···O1Wi0.96 (1)1.67 (1)2.628 (3)172 (4)
O1W—H1W1···O2Yiii0.94 (2)1.82 (2)2.757 (3)173 (4)
O1W—H1W2···O2Wiv0.94 (2)1.80 (2)2.740 (3)175 (4)
O2W—H2W1···O1X0.97 (2)1.83 (2)2.765 (3)161 (4)
O2W—H2W2···N1G0.98 (2)1.95 (2)2.923 (4)170 (4)
Symmetry codes: (i) x+1, y, z; (ii) x1, y, z; (iii) x, y+1, z; (iv) x, y+1, z.
(dc34x1) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 3,4-xylidine top
Crystal data top
C18H20O2/C8H11NF(000) = 1680
Mr = 389.52Dx = 1.195 Mg m3
Dm = N/A Mg m3
Dm measured by not measured
Monoclinic, C2/cMelting point: 463.15K for host melting K
a = 34.965 (1) ÅMo Kα radiation, λ = 0.71069 Å
b = 6.2546 (3) ŵ = 0.07 mm1
c = 20.2035 (8) ÅT = 173 K
β = 101.577 (1)°Prism, colourless
V = 4328.5 (3) Å30.35 × 0.25 × 0.20 mm
Z = 8
Data collection top
Nonius Kappa CCD
diffractometer
2949 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.111
Graphite monochromatorθmax = 28.2°, θmin = 2.1°
0.8° φ scans and ω scansh = 4344
7707 measured reflectionsk = 48
4699 independent reflectionsl = 2525
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.104H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.282 w = 1/[σ2(Fo2) + (0.P)2 + 16.4095P]
where P = (Fo2 + 2Fc2)/3
S = 1.16(Δ/σ)max < 0.001
4699 reflectionsΔρmax = 0.39 e Å3
278 parametersΔρmin = 0.30 e Å3
7 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0043 (8)
Special details top

Experimental. Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 55 mm; combination of φ and ω scans of 0.8°, 60 s per °, 2 iterations.

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*/Ueq
O10.14735 (8)0.8158 (5)0.23403 (15)0.0367 (8)
O20.15232 (9)0.7995 (5)0.67500 (15)0.0381 (8)
C100.12232 (11)0.7839 (8)0.27792 (19)0.0316 (10)
C70.07230 (11)0.7045 (7)0.36777 (19)0.0276 (9)
C10.04713 (11)0.6605 (8)0.4214 (2)0.0328 (10)
C160.12690 (11)0.7581 (7)0.6146 (2)0.0301 (9)
C80.07383 (12)0.9032 (8)0.3386 (2)0.0363 (10)
H80.05761.01410.34950.044*
C130.07420 (12)0.6939 (8)0.4911 (2)0.0341 (10)
C90.09848 (11)0.9472 (8)0.2936 (2)0.0348 (10)
H90.09891.08520.27410.042*
C110.12138 (12)0.5870 (8)0.3058 (2)0.0348 (10)
H110.13770.47640.29490.042*
C20.01159 (12)0.8115 (8)0.4126 (2)0.0391 (11)
H210.00170.79040.45100.047*
H220.02090.96130.41420.047*
C120.09666 (11)0.5464 (8)0.3504 (2)0.0356 (10)
H120.09630.40760.36940.043*
C140.07464 (13)0.8809 (8)0.5272 (2)0.0429 (12)
H140.05660.99060.51000.052*
C60.03078 (12)0.4296 (8)0.4153 (2)0.0357 (11)
H610.05270.32760.41860.043*
H620.01770.40130.45360.043*
C180.10088 (13)0.5367 (8)0.5197 (2)0.0438 (12)
H180.10130.40420.49690.053*
C150.10086 (14)0.9141 (8)0.5881 (2)0.0459 (12)
H150.10061.04590.61140.055*
C50.00156 (12)0.3908 (8)0.3486 (2)0.0430 (12)
H510.01510.40810.31030.052*
H520.00830.24220.34780.052*
C170.12681 (13)0.5688 (8)0.5805 (2)0.0427 (12)
H170.14460.45880.59860.051*
C40.03273 (13)0.5446 (9)0.3398 (3)0.0514 (14)
H410.04840.51530.37460.062*
H420.04970.52360.29480.062*
C30.01792 (13)0.7764 (9)0.3466 (2)0.0469 (13)
H310.00550.81110.30800.056*
H320.04030.87420.34510.056*
N1G0.20885 (10)0.5013 (6)0.21900 (17)0.0334 (9)
C1G0.23266 (11)0.6072 (7)0.1789 (2)0.0307 (9)
C2G0.21866 (12)0.7873 (7)0.1411 (2)0.0317 (9)
H2G0.19360.84160.14330.038*
C6G0.26906 (12)0.5285 (8)0.1753 (2)0.0402 (11)
H6G0.27910.40560.20050.048*
C3G0.24074 (12)0.8892 (8)0.1001 (2)0.0364 (11)
C7G0.22368 (15)1.0811 (8)0.0591 (2)0.0482 (13)
H7G10.22171.05100.01100.072*
H7G20.24061.20530.07200.072*
H7G30.19771.11140.06790.072*
C4G0.27737 (12)0.8099 (8)0.0966 (2)0.0379 (11)
C8G0.30226 (14)0.9151 (10)0.0524 (2)0.0529 (14)
H8G10.28850.91030.00510.079*
H8G20.32710.83860.05720.079*
H8G30.30731.06420.06630.079*
C5G0.29082 (12)0.6317 (9)0.1342 (2)0.0434 (12)
H5G0.31590.57700.13190.052*
H1G20.22580.42870.26510.12 (3)*
H1G10.1893 (9)0.597 (5)0.231 (2)0.023 (10)*
H10.1479 (12)0.961 (4)0.219 (2)0.033 (12)*
H20.1723 (11)0.692 (6)0.687 (2)0.053 (15)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0334 (16)0.050 (2)0.0305 (16)0.0030 (15)0.0161 (13)0.0017 (15)
O20.0387 (17)0.0494 (19)0.0237 (15)0.0124 (15)0.0001 (13)0.0060 (15)
C100.0227 (19)0.056 (3)0.0156 (18)0.0036 (19)0.0029 (15)0.0027 (19)
C70.0267 (19)0.039 (2)0.0165 (18)0.0043 (18)0.0034 (15)0.0046 (18)
C10.027 (2)0.051 (3)0.022 (2)0.0071 (19)0.0083 (16)0.006 (2)
C160.028 (2)0.043 (2)0.0191 (19)0.0051 (19)0.0045 (15)0.0005 (18)
C80.032 (2)0.053 (3)0.025 (2)0.007 (2)0.0102 (17)0.005 (2)
C130.029 (2)0.055 (3)0.021 (2)0.011 (2)0.0099 (16)0.006 (2)
C90.032 (2)0.049 (3)0.024 (2)0.000 (2)0.0069 (17)0.004 (2)
C110.031 (2)0.049 (3)0.026 (2)0.006 (2)0.0085 (17)0.008 (2)
C20.033 (2)0.060 (3)0.028 (2)0.016 (2)0.0136 (18)0.017 (2)
C120.030 (2)0.052 (3)0.026 (2)0.009 (2)0.0089 (17)0.010 (2)
C140.047 (3)0.051 (3)0.028 (2)0.021 (2)0.001 (2)0.005 (2)
C60.029 (2)0.056 (3)0.023 (2)0.005 (2)0.0098 (17)0.012 (2)
C180.046 (3)0.050 (3)0.032 (2)0.017 (2)0.002 (2)0.002 (2)
C150.052 (3)0.051 (3)0.032 (3)0.018 (2)0.002 (2)0.006 (2)
C50.034 (2)0.062 (3)0.032 (2)0.005 (2)0.0038 (19)0.018 (2)
C170.043 (3)0.050 (3)0.032 (2)0.017 (2)0.0017 (19)0.004 (2)
C40.029 (2)0.086 (4)0.037 (3)0.003 (3)0.001 (2)0.020 (3)
C30.028 (2)0.080 (4)0.033 (2)0.013 (2)0.0057 (19)0.014 (3)
N1G0.0311 (18)0.046 (2)0.0230 (18)0.0030 (17)0.0039 (14)0.0043 (17)
C1G0.028 (2)0.044 (2)0.0176 (19)0.0031 (19)0.0006 (15)0.0036 (18)
C2G0.030 (2)0.043 (2)0.0206 (19)0.0017 (19)0.0017 (16)0.0001 (19)
C6G0.034 (2)0.055 (3)0.029 (2)0.002 (2)0.0000 (18)0.004 (2)
C3G0.036 (2)0.054 (3)0.017 (2)0.006 (2)0.0032 (17)0.004 (2)
C7G0.059 (3)0.056 (3)0.032 (3)0.001 (3)0.013 (2)0.011 (2)
C4G0.031 (2)0.062 (3)0.019 (2)0.012 (2)0.0016 (16)0.009 (2)
C8G0.043 (3)0.085 (4)0.033 (3)0.019 (3)0.011 (2)0.002 (3)
C5G0.027 (2)0.070 (3)0.031 (2)0.003 (2)0.0023 (18)0.002 (2)
Geometric parameters (Å, º) top
O1—C101.379 (4)C18—H180.9500
O1—H10.95 (2)C15—H150.9500
O2—C161.383 (5)C5—C41.519 (6)
O2—H20.97 (2)C5—H510.9900
C10—C111.358 (6)C5—H520.9900
C10—C91.394 (6)C17—H170.9500
C7—C81.381 (6)C4—C31.536 (8)
C7—C121.396 (6)C4—H410.9900
C7—C11.551 (5)C4—H420.9900
C1—C21.542 (6)C3—H310.9900
C1—C131.546 (6)C3—H320.9900
C1—C61.549 (6)N1G—C1G1.434 (5)
C16—C151.368 (6)N1G—H1G21.0958
C16—C171.369 (6)N1G—H1G10.976 (19)
C8—C91.401 (5)C1G—C6G1.380 (6)
C8—H80.9500C1G—C2G1.393 (6)
C13—C141.377 (6)C2G—C3G1.394 (6)
C13—C181.398 (6)C2G—H2G0.9500
C9—H90.9500C6G—C5G1.393 (6)
C11—C121.390 (5)C6G—H6G0.9500
C11—H110.9500C3G—C4G1.389 (6)
C2—C31.530 (6)C3G—C7G1.511 (6)
C2—H210.9900C7G—H7G10.9800
C2—H220.9900C7G—H7G20.9800
C12—H120.9500C7G—H7G30.9800
C14—C151.395 (6)C4G—C5G1.377 (7)
C14—H140.9500C4G—C8G1.516 (6)
C6—C51.539 (6)C8G—H8G10.9800
C6—H610.9900C8G—H8G20.9800
C6—H620.9900C8G—H8G30.9800
C18—C171.386 (6)C5G—H5G0.9500
C10—O1—H1113 (2)C4—C5—H51109.3
C16—O2—H2113 (3)C6—C5—H51109.3
C11—C10—O1118.0 (4)C4—C5—H52109.3
C11—C10—C9120.3 (4)C6—C5—H52109.3
O1—C10—C9121.6 (4)H51—C5—H52107.9
C8—C7—C12116.9 (4)C16—C17—C18120.4 (4)
C8—C7—C1122.2 (4)C16—C17—H17119.8
C12—C7—C1120.7 (4)C18—C17—H17119.8
C2—C1—C13110.7 (4)C5—C4—C3110.1 (4)
C2—C1—C6106.6 (3)C5—C4—H41109.6
C13—C1—C6110.3 (4)C3—C4—H41109.6
C2—C1—C7111.6 (3)C5—C4—H42109.6
C13—C1—C7106.4 (3)C3—C4—H42109.6
C6—C1—C7111.3 (3)H41—C4—H42108.2
C15—C16—C17119.1 (4)C2—C3—C4111.7 (4)
C15—C16—O2118.1 (4)C2—C3—H31109.3
C17—C16—O2122.8 (4)C4—C3—H31109.3
C7—C8—C9122.4 (4)C2—C3—H32109.3
C7—C8—H8118.8C4—C3—H32109.3
C9—C8—H8118.8H31—C3—H32107.9
C14—C13—C18116.3 (4)C1G—N1G—H1G2113.3
C14—C13—C1122.5 (4)C1G—N1G—H1G1112 (2)
C18—C13—C1121.2 (4)H1G2—N1G—H1G1108.8
C10—C9—C8118.5 (4)C6G—C1G—C2G119.0 (4)
C10—C9—H9120.7C6G—C1G—N1G120.7 (4)
C8—C9—H9120.7C2G—C1G—N1G120.2 (4)
C10—C11—C12120.3 (4)C1G—C2G—C3G121.3 (4)
C10—C11—H11119.8C1G—C2G—H2G119.3
C12—C11—H11119.8C3G—C2G—H2G119.3
C3—C2—C1113.5 (4)C1G—C6G—C5G119.1 (4)
C3—C2—H21108.9C1G—C6G—H6G120.4
C1—C2—H21108.9C5G—C6G—H6G120.4
C3—C2—H22108.9C4G—C3G—C2G119.6 (4)
C1—C2—H22108.9C4G—C3G—C7G121.5 (4)
H21—C2—H22107.7C2G—C3G—C7G118.9 (4)
C11—C12—C7121.6 (4)C3G—C7G—H7G1109.5
C11—C12—H12119.2C3G—C7G—H7G2109.5
C7—C12—H12119.2H7G1—C7G—H7G2109.5
C13—C14—C15121.9 (4)C3G—C7G—H7G3109.5
C13—C14—H14119.0H7G1—C7G—H7G3109.5
C15—C14—H14119.0H7G2—C7G—H7G3109.5
C5—C6—C1112.7 (4)C5G—C4G—C3G118.5 (4)
C5—C6—H61109.1C5G—C4G—C8G120.2 (4)
C1—C6—H61109.1C3G—C4G—C8G121.3 (5)
C5—C6—H62109.1C4G—C8G—H8G1109.5
C1—C6—H62109.1C4G—C8G—H8G2109.5
H61—C6—H62107.8H8G1—C8G—H8G2109.5
C17—C18—C13121.9 (5)C4G—C8G—H8G3109.5
C17—C18—H18119.1H8G1—C8G—H8G3109.5
C13—C18—H18119.1H8G2—C8G—H8G3109.5
C16—C15—C14120.4 (5)C4G—C5G—C6G122.5 (4)
C16—C15—H15119.8C4G—C5G—H5G118.8
C14—C15—H15119.8C6G—C5G—H5G118.8
C4—C5—C6111.8 (4)
C8—C7—C1—C227.6 (6)C13—C1—C6—C5176.4 (3)
C12—C7—C1—C2156.9 (4)C7—C1—C6—C565.7 (4)
C8—C7—C1—C1393.4 (5)C14—C13—C18—C171.1 (7)
C12—C7—C1—C1382.2 (5)C1—C13—C18—C17176.4 (4)
C8—C7—C1—C6146.5 (4)C17—C16—C15—C140.1 (7)
C12—C7—C1—C638.0 (5)O2—C16—C15—C14179.8 (4)
C12—C7—C8—C90.0 (6)C13—C14—C15—C160.9 (7)
C1—C7—C8—C9175.7 (4)C1—C6—C5—C458.0 (5)
C2—C1—C13—C1423.0 (6)C15—C16—C17—C180.6 (7)
C6—C1—C13—C14140.7 (4)O2—C16—C17—C18179.4 (4)
C7—C1—C13—C1498.5 (5)C13—C18—C17—C160.1 (7)
C2—C1—C13—C18159.6 (4)C6—C5—C4—C354.4 (5)
C6—C1—C13—C1841.9 (5)C1—C2—C3—C456.9 (5)
C7—C1—C13—C1878.9 (5)C5—C4—C3—C253.8 (5)
C11—C10—C9—C80.2 (6)C6G—C1G—C2G—C3G0.3 (6)
O1—C10—C9—C8179.9 (4)N1G—C1G—C2G—C3G178.0 (4)
C7—C8—C9—C100.1 (6)C2G—C1G—C6G—C5G0.3 (6)
O1—C10—C11—C12180.0 (4)N1G—C1G—C6G—C5G177.9 (4)
C9—C10—C11—C120.1 (6)C1G—C2G—C3G—C4G0.2 (6)
C13—C1—C2—C3176.0 (4)C1G—C2G—C3G—C7G178.7 (4)
C6—C1—C2—C356.1 (4)C2G—C3G—C4G—C5G0.1 (6)
C7—C1—C2—C365.6 (5)C7G—C3G—C4G—C5G178.6 (4)
C10—C11—C12—C70.1 (7)C2G—C3G—C4G—C8G179.6 (4)
C8—C7—C12—C110.1 (6)C7G—C3G—C4G—C8G1.2 (7)
C1—C7—C12—C11175.6 (4)C3G—C4G—C5G—C6G0.1 (7)
C18—C13—C14—C151.5 (7)C8G—C4G—C5G—C6G179.7 (4)
C1—C13—C14—C15176.0 (4)C1G—C6G—C5G—C4G0.1 (7)
C2—C1—C6—C556.2 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.95 (2)1.77 (2)2.706 (4)166 (4)
O2—H2···N1Gii0.97 (2)1.78 (2)2.744 (5)173 (5)
N1G—H1G1···O10.98 (2)2.02 (2)2.975 (5)166 (3)
Symmetry codes: (i) x, y+2, z1/2; (ii) x, y+1, z+1/2.
(dc35x1) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 3,5-xylidine top
Crystal data top
C18H20O2/C8H11NZ = 2
Mr = 389.52F(000) = 420
Triclinic, P1Dx = 1.175 Mg m3
Dm = N/A Mg m3
Dm measured by not measured
a = 6.327 (1) ÅMelting point: 397.35K for guest release onset temp. and 463.15K for host melting K
b = 10.720 (2) ÅMo Kα radiation, λ = 0.71069 Å
c = 16.920 (4) ŵ = 0.07 mm1
α = 96.481 (15)°T = 293 K
β = 100.094 (17)°Prism, colourless
γ = 99.827 (14)°0.40 × 0.40 × 0.30 mm
V = 1101.1 (4) Å3
Data collection top
Nonius Kappa CCD
diffractometer
2067 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.039
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
φ scans and ω scansh = 07
4014 measured reflectionsk = 1212
3869 independent reflectionsl = 2019
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.137 w = 1/[σ2(Fo2) + (0.0323P)2 + 0.4445P]
where P = (Fo2 + 2Fc2)/3
S = 1.11(Δ/σ)max < 0.001
3869 reflectionsΔρmax = 0.20 e Å3
281 parametersΔρmin = 0.18 e Å3
7 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.038 (3)
Special details top

Experimental. Complete sphere of data collected using COLLECT strategy (Nonius, 2000). Crystal to detector distance = 40 mm; combination of φ and ω scans of 1°, 80 s per °, 2 iterations.

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*/Ueq
O20.3928 (4)0.68002 (18)0.72633 (12)0.0562 (6)
O10.0728 (3)0.18608 (18)0.68965 (12)0.0554 (6)
C70.1635 (4)0.1486 (2)0.85554 (15)0.0368 (6)
C10.1943 (4)0.2764 (2)0.91165 (15)0.0367 (6)
C90.2994 (4)0.0339 (3)0.80014 (16)0.0438 (7)
H90.41240.07940.80090.053*
C130.2417 (4)0.3844 (2)0.86143 (15)0.0364 (6)
C180.1246 (4)0.4822 (3)0.85518 (16)0.0445 (7)
H180.00780.48250.88170.053*
C100.1063 (4)0.0768 (2)0.74526 (15)0.0410 (7)
C150.4671 (4)0.4861 (3)0.77511 (17)0.0469 (7)
H150.58420.48670.74860.056*
C20.3880 (4)0.2939 (2)0.98404 (16)0.0421 (7)
H210.51930.28590.96330.051*
H220.41050.37991.01320.051*
C120.0291 (4)0.1022 (3)0.79878 (16)0.0451 (7)
H120.14230.14760.79740.054*
C170.1770 (5)0.5793 (3)0.81052 (16)0.0472 (7)
H170.09590.64390.80780.057*
C160.3472 (5)0.5814 (2)0.77016 (16)0.0423 (7)
C80.3265 (4)0.0771 (2)0.85449 (16)0.0428 (7)
H80.45820.10450.89150.051*
C110.0594 (5)0.0081 (3)0.74460 (16)0.0470 (7)
H110.19110.03630.70770.056*
C140.4127 (4)0.3893 (3)0.81962 (17)0.0463 (7)
H140.49390.32470.82170.056*
C60.0097 (4)0.2838 (3)0.94901 (16)0.0435 (7)
H610.00650.36890.97870.052*
H620.13760.27000.90570.052*
C50.0457 (5)0.1852 (3)1.00624 (17)0.0520 (8)
H510.17530.19381.02800.062*
H520.07010.09980.97610.062*
C30.3576 (4)0.1986 (3)1.04353 (16)0.0456 (7)
H310.35170.11301.01650.055*
H320.48190.21861.08860.055*
C40.1493 (5)0.2027 (3)1.07547 (17)0.0547 (8)
H410.16380.28421.10930.066*
H420.12600.13551.10870.066*
N1G0.3627 (5)0.3557 (3)0.38669 (15)0.0566 (7)
C1G0.4510 (5)0.3065 (3)0.45744 (17)0.0514 (8)
C6G0.6615 (5)0.3584 (3)0.49912 (19)0.0604 (9)
H6G0.74300.42590.48080.072*
C2G0.3325 (6)0.2049 (3)0.4840 (2)0.0681 (9)
H2G0.19130.16860.45610.082*
C5G0.7535 (6)0.3125 (3)0.5673 (2)0.0679 (9)
C3G0.4218 (7)0.1564 (4)0.5519 (2)0.0815 (12)
C4G0.6302 (7)0.2121 (4)0.5931 (2)0.0816 (11)
H4G0.68920.18110.63950.098*
C7G0.2902 (8)0.0446 (5)0.5805 (3)0.138 (2)
H7G10.38610.00780.61760.207*
H7G20.21860.01880.53470.207*
H7G30.18240.07400.60740.207*
C8G0.9838 (6)0.3696 (4)0.6128 (3)0.1075 (15)
H8G11.00880.33790.66380.161*
H8G21.00210.46110.62230.161*
H8G31.08660.34590.58120.161*
H1G20.380 (6)0.4472 (18)0.397 (2)0.092 (12)*
H1G10.212 (3)0.315 (3)0.365 (2)0.094 (13)*
H20.486 (6)0.667 (4)0.6871 (19)0.119 (15)*
H10.197 (4)0.226 (3)0.706 (2)0.111 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O20.0760 (15)0.0466 (12)0.0604 (13)0.0224 (10)0.0313 (12)0.0249 (10)
O10.0680 (15)0.0448 (12)0.0490 (12)0.0140 (11)0.0011 (11)0.0002 (10)
C70.0390 (15)0.0402 (15)0.0364 (14)0.0121 (12)0.0126 (12)0.0135 (12)
C10.0343 (14)0.0378 (15)0.0412 (15)0.0105 (12)0.0105 (12)0.0101 (12)
C90.0444 (17)0.0461 (17)0.0460 (16)0.0191 (13)0.0093 (14)0.0116 (14)
C130.0378 (15)0.0383 (15)0.0353 (14)0.0083 (12)0.0105 (12)0.0082 (11)
C180.0485 (17)0.0471 (16)0.0464 (16)0.0198 (14)0.0189 (14)0.0111 (13)
C100.0521 (18)0.0381 (15)0.0343 (15)0.0098 (13)0.0086 (14)0.0101 (12)
C150.0450 (17)0.0503 (17)0.0546 (18)0.0144 (14)0.0228 (14)0.0186 (14)
C20.0429 (16)0.0406 (15)0.0434 (16)0.0073 (12)0.0100 (13)0.0075 (12)
C120.0417 (16)0.0460 (17)0.0489 (17)0.0161 (13)0.0043 (14)0.0078 (14)
C170.0592 (19)0.0413 (16)0.0519 (17)0.0221 (14)0.0236 (15)0.0138 (14)
C160.0539 (18)0.0350 (15)0.0402 (15)0.0091 (13)0.0117 (13)0.0105 (12)
C80.0413 (16)0.0430 (16)0.0427 (16)0.0096 (13)0.0032 (12)0.0059 (13)
C110.0419 (17)0.0492 (17)0.0452 (17)0.0091 (13)0.0026 (13)0.0050 (14)
C140.0460 (17)0.0458 (16)0.0567 (18)0.0187 (13)0.0194 (14)0.0193 (14)
C60.0411 (16)0.0469 (16)0.0470 (16)0.0126 (13)0.0143 (13)0.0113 (13)
C50.0481 (18)0.0597 (19)0.0576 (19)0.0156 (15)0.0239 (15)0.0195 (15)
C30.0476 (17)0.0522 (17)0.0374 (15)0.0109 (13)0.0057 (13)0.0100 (13)
C40.064 (2)0.062 (2)0.0477 (18)0.0174 (16)0.0228 (16)0.0200 (15)
N1G0.068 (2)0.0575 (18)0.0474 (15)0.0114 (15)0.0158 (14)0.0138 (13)
C1G0.060 (2)0.0566 (19)0.0404 (16)0.0119 (15)0.0176 (15)0.0048 (14)
C6G0.065 (2)0.056 (2)0.059 (2)0.0004 (16)0.0190 (17)0.0077 (16)
C2G0.065 (2)0.078 (2)0.056 (2)0.0053 (18)0.0108 (17)0.0189 (18)
C5G0.068 (2)0.072 (2)0.056 (2)0.0076 (19)0.0051 (18)0.0016 (18)
C3G0.087 (3)0.092 (3)0.062 (2)0.007 (2)0.013 (2)0.036 (2)
C4G0.090 (3)0.096 (3)0.053 (2)0.008 (2)0.002 (2)0.022 (2)
C7G0.131 (4)0.155 (5)0.115 (4)0.035 (3)0.008 (3)0.082 (4)
C8G0.082 (3)0.124 (4)0.093 (3)0.001 (3)0.016 (2)0.001 (3)
Geometric parameters (Å, º) top
O2—C161.378 (3)C6—C51.527 (4)
O2—H20.978 (14)C6—H610.9700
O1—C101.378 (3)C6—H620.9700
O1—H10.970 (14)C5—C41.515 (4)
C7—C81.388 (3)C5—H510.9700
C7—C121.389 (4)C5—H520.9700
C7—C11.539 (4)C3—C41.515 (4)
C1—C131.531 (3)C3—H310.9700
C1—C61.543 (3)C3—H320.9700
C1—C21.543 (3)C4—H410.9700
C9—C101.372 (4)C4—H420.9700
C9—C81.385 (4)N1G—C1G1.425 (4)
C9—H90.9300N1G—H1G20.960 (18)
C13—C181.386 (3)N1G—H1G10.966 (14)
C13—C141.390 (3)C1G—C2G1.379 (4)
C18—C171.383 (4)C1G—C6G1.382 (4)
C18—H180.9300C6G—C5G1.379 (4)
C10—C111.380 (4)C6G—H6G0.9300
C15—C161.375 (4)C2G—C3G1.385 (5)
C15—C141.381 (4)C2G—H2G0.9300
C15—H150.9300C5G—C4G1.378 (5)
C2—C31.525 (3)C5G—C8G1.512 (5)
C2—H210.9700C3G—C4G1.377 (5)
C2—H220.9700C3G—C7G1.515 (5)
C12—C111.376 (4)C4G—H4G0.9300
C12—H120.9300C7G—H7G10.9600
C17—C161.371 (4)C7G—H7G20.9600
C17—H170.9300C7G—H7G30.9600
C8—H80.9300C8G—H8G10.9600
C11—H110.9300C8G—H8G20.9600
C14—H140.9300C8G—H8G30.9600
C16—O2—H2116 (2)C1—C6—H62109.1
C10—O1—H1105 (2)H61—C6—H62107.8
C8—C7—C12116.0 (2)C4—C5—C6111.3 (2)
C8—C7—C1123.2 (2)C4—C5—H51109.4
C12—C7—C1120.7 (2)C6—C5—H51109.4
C13—C1—C7107.7 (2)C4—C5—H52109.4
C13—C1—C6112.0 (2)C6—C5—H52109.4
C7—C1—C6110.8 (2)H51—C5—H52108.0
C13—C1—C2108.0 (2)C4—C3—C2111.1 (2)
C7—C1—C2112.5 (2)C4—C3—H31109.4
C6—C1—C2105.9 (2)C2—C3—H31109.4
C10—C9—C8120.1 (3)C4—C3—H32109.4
C10—C9—H9120.0C2—C3—H32109.4
C8—C9—H9120.0H31—C3—H32108.0
C18—C13—C14116.1 (2)C3—C4—C5110.8 (2)
C18—C13—C1123.9 (2)C3—C4—H41109.5
C14—C13—C1120.1 (2)C5—C4—H41109.5
C17—C18—C13121.7 (2)C3—C4—H42109.5
C17—C18—H18119.1C5—C4—H42109.5
C13—C18—H18119.1H41—C4—H42108.1
C9—C10—O1122.1 (2)C1G—N1G—H1G2111 (2)
C9—C10—C11119.3 (3)C1G—N1G—H1G1112 (2)
O1—C10—C11118.6 (2)H1G2—N1G—H1G1112 (3)
C16—C15—C14119.6 (3)C2G—C1G—C6G119.0 (3)
C16—C15—H15120.2C2G—C1G—N1G121.2 (3)
C14—C15—H15120.2C6G—C1G—N1G119.8 (3)
C3—C2—C1114.3 (2)C5G—C6G—C1G121.5 (3)
C3—C2—H21108.7C5G—C6G—H6G119.2
C1—C2—H21108.7C1G—C6G—H6G119.2
C3—C2—H22108.7C1G—C2G—C3G120.6 (3)
C1—C2—H22108.7C1G—C2G—H2G119.7
H21—C2—H22107.6C3G—C2G—H2G119.7
C11—C12—C7122.7 (3)C4G—C5G—C6G118.2 (3)
C11—C12—H12118.7C4G—C5G—C8G120.4 (3)
C7—C12—H12118.7C6G—C5G—C8G121.4 (3)
C16—C17—C18120.7 (2)C4G—C3G—C2G119.0 (3)
C16—C17—H17119.6C4G—C3G—C7G120.9 (3)
C18—C17—H17119.6C2G—C3G—C7G120.2 (4)
C17—C16—C15119.1 (2)C3G—C4G—C5G121.7 (3)
C17—C16—O2118.6 (2)C3G—C4G—H4G119.2
C15—C16—O2122.3 (2)C5G—C4G—H4G119.2
C9—C8—C7122.2 (3)C3G—C7G—H7G1109.5
C9—C8—H8118.9C3G—C7G—H7G2109.5
C7—C8—H8118.9H7G1—C7G—H7G2109.5
C12—C11—C10119.7 (3)C3G—C7G—H7G3109.5
C12—C11—H11120.1H7G1—C7G—H7G3109.5
C10—C11—H11120.1H7G2—C7G—H7G3109.5
C15—C14—C13122.7 (2)C5G—C8G—H8G1109.5
C15—C14—H14118.6C5G—C8G—H8G2109.5
C13—C14—H14118.6H8G1—C8G—H8G2109.5
C5—C6—C1112.6 (2)C5G—C8G—H8G3109.5
C5—C6—H61109.1H8G1—C8G—H8G3109.5
C1—C6—H61109.1H8G2—C8G—H8G3109.5
C5—C6—H62109.1
C8—C7—C1—C1399.9 (3)C12—C7—C8—C90.1 (4)
C12—C7—C1—C1376.2 (3)C1—C7—C8—C9176.1 (2)
C8—C7—C1—C6137.4 (2)C7—C12—C11—C100.3 (4)
C12—C7—C1—C646.6 (3)C9—C10—C11—C120.0 (4)
C8—C7—C1—C219.0 (3)O1—C10—C11—C12179.2 (2)
C12—C7—C1—C2164.9 (2)C16—C15—C14—C131.0 (4)
C7—C1—C13—C18126.4 (3)C18—C13—C14—C150.9 (4)
C6—C1—C13—C184.3 (3)C1—C13—C14—C15178.2 (3)
C2—C1—C13—C18111.9 (3)C13—C1—C6—C5174.1 (2)
C7—C1—C13—C1454.6 (3)C7—C1—C6—C565.7 (3)
C6—C1—C13—C14176.6 (2)C2—C1—C6—C556.6 (3)
C2—C1—C13—C1467.2 (3)C1—C6—C5—C459.0 (3)
C14—C13—C18—C170.6 (4)C1—C2—C3—C456.0 (3)
C1—C13—C18—C17178.5 (3)C2—C3—C4—C553.3 (3)
C8—C9—C10—O1179.4 (2)C6—C5—C4—C355.3 (3)
C8—C9—C10—C110.3 (4)C2G—C1G—C6G—C5G1.3 (5)
C13—C1—C2—C3175.9 (2)N1G—C1G—C6G—C5G179.3 (3)
C7—C1—C2—C365.4 (3)C6G—C1G—C2G—C3G0.7 (5)
C6—C1—C2—C355.8 (3)N1G—C1G—C2G—C3G178.7 (3)
C8—C7—C12—C110.2 (4)C1G—C6G—C5G—C4G0.4 (5)
C1—C7—C12—C11176.6 (2)C1G—C6G—C5G—C8G180.0 (3)
C13—C18—C17—C160.5 (4)C1G—C2G—C3G—C4G0.7 (6)
C18—C17—C16—C150.5 (4)C1G—C2G—C3G—C7G180.0 (4)
C18—C17—C16—O2179.9 (3)C2G—C3G—C4G—C5G1.7 (6)
C14—C15—C16—C170.8 (4)C7G—C3G—C4G—C5G179.0 (4)
C14—C15—C16—O2179.6 (3)C6G—C5G—C4G—C3G1.1 (6)
C10—C9—C8—C70.4 (4)C8G—C5G—C4G—C3G178.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O2—H2···N1Gi0.98 (1)1.72 (1)2.697 (3)176 (4)
O1—H1···O2ii0.97 (1)1.74 (1)2.701 (3)171 (3)
N1G—H1G1···O1iii0.97 (1)2.07 (2)3.013 (4)165 (3)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x, y1, z; (iii) x, y, z+1.
 

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