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
CCDC references: 184876; 184877; 184878; 184879; 184880; 184881; 184882; 184883; 184884
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/C8H11N | Z = 2 |
Mr = 389.52 | F(000) = 420 |
Triclinic, P1 | Dx = 1.162 Mg m−3 Dm = N/A Mg m−3 Dm measured by not measured |
a = 6.234 (1) Å | Melting point: 365.55K for guest release onset temp. and 463.15K for host melting K |
b = 10.934 (2) Å | Mo Kα radiation, λ = 0.71070 Å |
c = 16.974 (2) Å | µ = 0.07 mm−1 |
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 tube | Rint = 0.018 |
Graphite monochromator | θmax = 25.0°, θmin = 1.9° |
1° φ scans and ω scans | h = 0→7 |
4040 measured reflections | k = −12→12 |
3895 independent reflections | l = −19→20 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H 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 reflections | Δρmax = 0.78 e Å−3 |
347 parameters | Δρmin = −0.17 e Å−3 |
20 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.1197 (4) | 0.36309 (18) | 0.79798 (12) | 0.0613 (6) | |
C1 | 0.2289 (4) | 0.7892 (2) | 0.58660 (14) | 0.0361 (5) | |
O2 | −0.1639 (3) | 1.21323 (19) | 0.77408 (13) | 0.0627 (6) | |
C2 | 0.1009 (4) | 0.8025 (2) | 0.51394 (15) | 0.0417 (6) | |
H21 | −0.0535 | 0.8016 | 0.5331 | 0.050* | |
H22 | 0.1056 | 0.8834 | 0.4861 | 0.050* | |
C3 | 0.1913 (4) | 0.6999 (3) | 0.45497 (15) | 0.0473 (6) | |
H31 | 0.1696 | 0.6198 | 0.4804 | 0.057* | |
H32 | 0.1094 | 0.7176 | 0.4096 | 0.057* | |
C4 | 0.4368 (5) | 0.6910 (3) | 0.42602 (17) | 0.0554 (7) | |
H41 | 0.4929 | 0.6194 | 0.3932 | 0.066* | |
H42 | 0.4568 | 0.7662 | 0.3935 | 0.066* | |
C5 | 0.5667 (4) | 0.6770 (3) | 0.49590 (17) | 0.0513 (7) | |
H51 | 0.7210 | 0.6773 | 0.4762 | 0.062* | |
H52 | 0.5609 | 0.5969 | 0.5247 | 0.062* | |
C6 | 0.4741 (4) | 0.7827 (2) | 0.55258 (16) | 0.0430 (6) | |
H61 | 0.4884 | 0.8622 | 0.5243 | 0.052* | |
H62 | 0.5617 | 0.7705 | 0.5964 | 0.052* | |
C7 | 0.2033 (4) | 0.6718 (2) | 0.64147 (14) | 0.0380 (6) | |
C8 | 0.3412 (4) | 0.6289 (2) | 0.69972 (16) | 0.0474 (6) | |
H8 | 0.4530 | 0.6708 | 0.7040 | 0.057* | |
C9 | 0.3186 (5) | 0.5274 (3) | 0.75100 (16) | 0.0505 (7) | |
H9 | 0.4162 | 0.5009 | 0.7885 | 0.061* | |
C10 | 0.1528 (4) | 0.4643 (2) | 0.74753 (15) | 0.0441 (6) | |
C11 | 0.0113 (4) | 0.5048 (2) | 0.69115 (16) | 0.0489 (7) | |
H11 | −0.1026 | 0.4637 | 0.6883 | 0.059* | |
C12 | 0.0376 (4) | 0.6059 (2) | 0.63904 (16) | 0.0448 (6) | |
H12 | −0.0586 | 0.6310 | 0.6010 | 0.054* | |
C13 | 0.1328 (4) | 0.9043 (2) | 0.63672 (14) | 0.0381 (6) | |
C14 | 0.2515 (4) | 0.9919 (2) | 0.64947 (16) | 0.0472 (6) | |
H14 | 0.3993 | 0.9816 | 0.6267 | 0.057* | |
C15 | 0.1573 (4) | 1.0947 (2) | 0.69510 (17) | 0.0507 (7) | |
H15 | 0.2422 | 1.1513 | 0.7031 | 0.061* | |
C16 | −0.0618 (4) | 1.1124 (2) | 0.72846 (15) | 0.0457 (6) | |
C17 | −0.1846 (4) | 1.0279 (3) | 0.71625 (17) | 0.0538 (7) | |
H17 | −0.3333 | 1.0396 | 0.7381 | 0.065* | |
C18 | −0.0880 (4) | 0.9263 (3) | 0.67190 (17) | 0.0497 (7) | |
H18 | −0.1736 | 0.8694 | 0.6650 | 0.060* | |
N1GA | 0.4320 (10) | 0.2979 (6) | 0.9128 (4) | 0.0677 (16) | 0.500 (4) |
C1GA | 0.3272 (17) | 0.2419 (8) | 0.9783 (4) | 0.048 (3) | 0.535 (17) |
C2GA | 0.2248 (13) | 0.3084 (6) | 1.0490 (4) | 0.083 (2) | 0.500 (4) |
C3GA | 0.1183 (19) | 0.2511 (10) | 1.1075 (5) | 0.094 (8) | 0.500 (4) |
H3GA | 0.0557 | 0.2971 | 1.1520 | 0.113* | 0.500 (4) |
C4GA | 0.0893 (17) | 0.1324 (10) | 1.1105 (5) | 0.103 (3) | 0.500 (4) |
H4GA | 0.0072 | 0.0989 | 1.1541 | 0.124* | 0.500 (4) |
C5GA | 0.1870 (15) | 0.0633 (8) | 1.0459 (5) | 0.095 (3) | 0.500 (4) |
H5GA | 0.1748 | −0.0199 | 1.0456 | 0.114* | 0.500 (4) |
C6GA | 0.3042 (12) | 0.1169 (6) | 0.9808 (4) | 0.0693 (19) | 0.500 (4) |
C7GA | 0.242 (2) | 0.4412 (12) | 1.0505 (9) | 0.166 (6) | 0.500 (4) |
H7A1 | 0.1296 | 0.4824 | 1.0904 | 0.249* | 0.500 (4) |
H7A2 | 0.2216 | 0.4831 | 0.9992 | 0.249* | 0.500 (4) |
H7A3 | 0.3860 | 0.4442 | 1.0628 | 0.249* | 0.500 (4) |
C8GA | 0.4103 (16) | 0.0416 (7) | 0.9089 (5) | 0.100 (3) | 0.500 (4) |
H8A1 | 0.3496 | −0.0321 | 0.9107 | 0.150* | 0.500 (4) |
H8A2 | 0.5678 | 0.0171 | 0.9096 | 0.150* | 0.500 (4) |
H8A3 | 0.3807 | 0.0920 | 0.8610 | 0.150* | 0.500 (4) |
N1GB | 0.4038 (9) | 0.2269 (6) | 0.8889 (3) | 0.0577 (14) | 0.500 (4) |
C1GB | 0.3644 (10) | 0.2537 (6) | 0.9722 (5) | 0.084 (7) | 0.500 (4) |
C2GB | 0.1664 (11) | 0.2251 (5) | 1.0144 (3) | 0.080 (2) | 0.500 (4) |
C3GB | 0.110 (2) | 0.2517 (7) | 1.1032 (3) | 0.136 (13) | 0.500 (4) |
H3GB | −0.0170 | 0.2366 | 1.1351 | 0.163* | 0.500 (4) |
C4GB | 0.269 (2) | 0.3005 (12) | 1.1307 (6) | 0.131 (5) | 0.500 (4) |
H4GB | 0.2477 | 0.3171 | 1.1845 | 0.157* | 0.500 (4) |
C5GB | 0.4511 (18) | 0.3256 (9) | 1.0866 (5) | 0.105 (3) | 0.500 (4) |
H5GB | 0.5469 | 0.3596 | 1.1108 | 0.126* | 0.500 (4) |
C6GB | 0.5043 (13) | 0.3035 (6) | 1.0061 (4) | 0.0718 (19) | 0.500 (4) |
C7GB | 0.0047 (11) | 0.1727 (6) | 0.9762 (5) | 0.123 (4) | 0.500 (4) |
H7B1 | −0.0221 | 0.2195 | 0.9268 | 0.185* | 0.500 (4) |
H7B2 | −0.1326 | 0.1794 | 1.0115 | 0.185* | 0.500 (4) |
H7B3 | 0.0663 | 0.0861 | 0.9660 | 0.185* | 0.500 (4) |
C8GB | 0.7084 (15) | 0.3327 (8) | 0.9581 (6) | 0.097 (3) | 0.500 (4) |
H8B1 | 0.8078 | 0.2560 | 0.9416 | 0.146* | 0.500 (4) |
H8B2 | 0.7799 | 0.3758 | 0.9897 | 0.146* | 0.500 (4) |
H8B3 | 0.6694 | 0.3851 | 0.9118 | 0.146* | 0.500 (4) |
H1 | 0.2492 | 0.3384 | 0.8255 | 0.125 (17)* | |
H2 | −0.0522 | 1.2606 | 0.7805 | 0.17 (2)* | |
H1A2 | 0.5361 | 0.2585 | 0.8702 | 0.14 (4)* | 0.500 (4) |
H1A1 | 0.4678 | 0.3761 | 0.9215 | 0.10 (3)* | 0.500 (4) |
H1B1 | 0.3936 | 0.1513 | 0.8682 | 0.12 (3)* | 0.500 (4) |
H1B2 | 0.5625 | 0.2200 | 0.8813 | 0.031 (13)* | 0.500 (4) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0802 (15) | 0.0503 (11) | 0.0568 (12) | −0.0255 (10) | −0.0079 (11) | 0.0054 (9) |
C1 | 0.0306 (11) | 0.0368 (12) | 0.0413 (13) | −0.0087 (9) | −0.0037 (10) | −0.0011 (10) |
O2 | 0.0640 (13) | 0.0545 (12) | 0.0676 (13) | −0.0107 (10) | 0.0077 (10) | −0.0250 (10) |
C2 | 0.0384 (13) | 0.0421 (13) | 0.0438 (14) | −0.0092 (10) | −0.0047 (10) | 0.0024 (11) |
C3 | 0.0492 (15) | 0.0513 (15) | 0.0422 (14) | −0.0101 (12) | −0.0071 (11) | −0.0069 (12) |
C4 | 0.0545 (16) | 0.0591 (17) | 0.0490 (16) | −0.0103 (13) | 0.0049 (13) | −0.0095 (13) |
C5 | 0.0357 (13) | 0.0516 (16) | 0.0647 (18) | −0.0082 (11) | 0.0026 (12) | −0.0122 (13) |
C6 | 0.0337 (12) | 0.0434 (14) | 0.0528 (15) | −0.0114 (10) | −0.0040 (11) | −0.0029 (11) |
C7 | 0.0335 (12) | 0.0371 (13) | 0.0438 (13) | −0.0089 (10) | −0.0028 (10) | −0.0055 (10) |
C8 | 0.0471 (14) | 0.0501 (15) | 0.0506 (15) | −0.0199 (12) | −0.0122 (12) | 0.0006 (12) |
C9 | 0.0561 (16) | 0.0529 (16) | 0.0456 (15) | −0.0151 (13) | −0.0154 (12) | 0.0045 (12) |
C10 | 0.0570 (16) | 0.0345 (12) | 0.0394 (13) | −0.0126 (11) | 0.0019 (11) | −0.0014 (10) |
C11 | 0.0518 (15) | 0.0504 (15) | 0.0518 (15) | −0.0258 (12) | −0.0075 (12) | −0.0027 (12) |
C12 | 0.0440 (14) | 0.0482 (15) | 0.0459 (14) | −0.0144 (11) | −0.0116 (11) | −0.0016 (12) |
C13 | 0.0376 (12) | 0.0361 (12) | 0.0409 (13) | −0.0090 (10) | −0.0045 (10) | −0.0020 (10) |
C14 | 0.0407 (13) | 0.0448 (14) | 0.0571 (16) | −0.0152 (11) | 0.0021 (12) | −0.0078 (12) |
C15 | 0.0504 (15) | 0.0432 (14) | 0.0621 (17) | −0.0185 (12) | −0.0012 (13) | −0.0123 (13) |
C16 | 0.0524 (15) | 0.0397 (14) | 0.0423 (14) | −0.0063 (11) | 0.0002 (12) | −0.0077 (11) |
C17 | 0.0382 (14) | 0.0639 (18) | 0.0608 (17) | −0.0156 (12) | 0.0043 (12) | −0.0181 (14) |
C18 | 0.0419 (14) | 0.0525 (15) | 0.0576 (16) | −0.0173 (12) | 0.0012 (12) | −0.0150 (13) |
N1GA | 0.069 (4) | 0.071 (4) | 0.063 (4) | −0.026 (3) | 0.004 (3) | −0.001 (3) |
C1GA | 0.046 (4) | 0.048 (5) | 0.045 (5) | 0.001 (4) | −0.002 (4) | −0.005 (4) |
C2GA | 0.078 (5) | 0.086 (6) | 0.084 (6) | −0.011 (4) | −0.005 (4) | −0.024 (5) |
C3GA | 0.068 (9) | 0.15 (2) | 0.062 (9) | −0.018 (10) | 0.012 (7) | −0.033 (11) |
C4GA | 0.124 (8) | 0.129 (8) | 0.054 (5) | −0.034 (7) | −0.007 (5) | 0.014 (5) |
C5GA | 0.124 (7) | 0.070 (5) | 0.086 (6) | −0.014 (5) | −0.026 (5) | 0.022 (4) |
C6GA | 0.081 (5) | 0.065 (4) | 0.051 (4) | 0.003 (3) | −0.010 (3) | 0.012 (3) |
C7GA | 0.175 (12) | 0.140 (10) | 0.185 (12) | −0.071 (9) | 0.080 (10) | −0.098 (10) |
C8GA | 0.129 (7) | 0.066 (5) | 0.092 (6) | −0.002 (5) | −0.001 (5) | −0.011 (4) |
N1GB | 0.059 (3) | 0.058 (3) | 0.055 (3) | −0.011 (3) | −0.011 (2) | 0.002 (3) |
C1GB | 0.082 (10) | 0.081 (10) | 0.085 (11) | 0.000 (7) | −0.025 (7) | −0.002 (8) |
C2GB | 0.078 (5) | 0.088 (6) | 0.059 (4) | 0.000 (4) | 0.000 (4) | 0.022 (4) |
C3GB | 0.13 (2) | 0.104 (17) | 0.126 (18) | 0.021 (13) | 0.020 (13) | 0.047 (12) |
C4GB | 0.140 (10) | 0.146 (10) | 0.069 (6) | 0.023 (8) | 0.028 (7) | −0.010 (6) |
C5GB | 0.138 (8) | 0.098 (6) | 0.071 (5) | 0.011 (6) | −0.031 (6) | −0.034 (5) |
C6GB | 0.079 (5) | 0.065 (4) | 0.069 (4) | −0.004 (4) | −0.014 (4) | −0.014 (3) |
C7GB | 0.098 (7) | 0.157 (10) | 0.118 (8) | −0.057 (7) | −0.011 (6) | 0.040 (7) |
C8GB | 0.107 (7) | 0.087 (6) | 0.105 (6) | −0.026 (5) | −0.022 (5) | −0.020 (5) |
Geometric parameters (Å, º) top
O1—C10 | 1.373 (3) | N1GA—H1A2 | 0.9581 |
O1—H1 | 0.9676 | N1GA—H1A1 | 0.9589 |
C1—C13 | 1.538 (3) | N1GA—H1B2 | 1.1457 |
C1—C6 | 1.539 (3) | C1GA—C6GA | 1.403 (12) |
C1—C7 | 1.542 (3) | C1GA—C2GA | 1.4451 |
C1—C2 | 1.547 (3) | C2GA—C3GA | 1.3032 |
O2—C16 | 1.381 (3) | C2GA—C7GA | 1.483 (13) |
O2—H2 | 0.9794 | C3GA—C4GA | 1.345 (13) |
C2—C3 | 1.523 (3) | C3GA—H3GA | 0.9300 |
C2—H21 | 0.9700 | C4GA—C5GA | 1.372 (11) |
C2—H22 | 0.9700 | C4GA—H4GA | 0.9300 |
C3—C4 | 1.519 (4) | C5GA—C6GA | 1.390 (10) |
C3—H31 | 0.9700 | C5GA—H5GA | 0.9300 |
C3—H32 | 0.9700 | C6GA—C8GA | 1.513 (10) |
C4—C5 | 1.513 (4) | C7GA—H7A1 | 0.9600 |
C4—H41 | 0.9700 | C7GA—H7A2 | 0.9600 |
C4—H42 | 0.9700 | C7GA—H7A3 | 0.9600 |
C5—C6 | 1.525 (4) | C8GA—H8A1 | 0.9600 |
C5—H51 | 0.9700 | C8GA—H8A2 | 0.9600 |
C5—H52 | 0.9700 | C8GA—H8A3 | 0.9600 |
C6—H61 | 0.9700 | C8GA—H1B1 | 1.3225 |
C6—H62 | 0.9700 | N1GB—C1GB | 1.444 (10) |
C7—C8 | 1.390 (4) | N1GB—H1A2 | 0.9637 |
C7—C12 | 1.392 (3) | N1GB—H1B1 | 0.9448 |
C8—C9 | 1.368 (4) | N1GB—H1B2 | 0.9648 |
C8—H8 | 0.9300 | C1GB—C6GB | 1.344 (10) |
C9—C10 | 1.376 (4) | C1GB—C2GB | 1.4139 |
C9—H9 | 0.9300 | C2GB—C7GB | 1.5118 |
C10—C11 | 1.378 (4) | C2GB—C3GB | 1.5317 |
C11—C12 | 1.377 (4) | C3GB—C4GB | 1.381 (16) |
C11—H11 | 0.9300 | C3GB—H3GB | 0.9300 |
C12—H12 | 0.9300 | C4GB—C5GB | 1.329 (13) |
C13—C14 | 1.383 (3) | C4GB—H4GB | 0.9300 |
C13—C18 | 1.392 (3) | C5GB—C6GB | 1.386 (10) |
C14—C15 | 1.388 (4) | C5GB—H5GB | 0.9300 |
C14—H14 | 0.9300 | C6GB—C8GB | 1.485 (11) |
C15—C16 | 1.375 (4) | C7GB—H7B1 | 0.9600 |
C15—H15 | 0.9300 | C7GB—H7B2 | 0.9600 |
C16—C17 | 1.372 (4) | C7GB—H7B3 | 0.9600 |
C17—C18 | 1.369 (4) | C8GB—H8B1 | 0.9600 |
C17—H17 | 0.9300 | C8GB—H8B2 | 0.9600 |
C18—H18 | 0.9300 | C8GB—H8B3 | 0.9600 |
N1GA—C1GA | 1.370 (10) | | |
| | | |
C10—O1—H1 | 106.1 | C16—C15—H15 | 120.1 |
C13—C1—C6 | 111.72 (19) | C14—C15—H15 | 120.1 |
C13—C1—C7 | 107.17 (19) | C17—C16—C15 | 119.4 (2) |
C6—C1—C7 | 110.68 (19) | C17—C16—O2 | 118.4 (2) |
C13—C1—C2 | 108.33 (18) | C15—C16—O2 | 122.2 (2) |
C6—C1—C2 | 106.38 (19) | C18—C17—C16 | 119.9 (2) |
C7—C1—C2 | 112.62 (19) | C18—C17—H17 | 120.0 |
C16—O2—H2 | 108.4 | C16—C17—H17 | 120.0 |
C3—C2—C1 | 114.1 (2) | C17—C18—C13 | 122.9 (2) |
C3—C2—H21 | 108.7 | C17—C18—H18 | 118.6 |
C1—C2—H21 | 108.7 | C13—C18—H18 | 118.6 |
C3—C2—H22 | 108.7 | N1GA—C1GA—C6GA | 122.5 (6) |
C1—C2—H22 | 108.7 | N1GA—C1GA—C2GA | 122.6 (7) |
H21—C2—H22 | 107.6 | C6GA—C1GA—C2GA | 114.8 (6) |
C4—C3—C2 | 111.6 (2) | C3GA—C2GA—C1GA | 119.3 |
C4—C3—H31 | 109.3 | C3GA—C2GA—C7GA | 122.9 (7) |
C2—C3—H31 | 109.3 | C1GA—C2GA—C7GA | 117.8 (7) |
C4—C3—H32 | 109.3 | C2GA—C3GA—C4GA | 126.9 (7) |
C2—C3—H32 | 109.3 | C2GA—C3GA—H3GA | 116.5 |
H31—C3—H32 | 108.0 | C4GA—C3GA—H3GA | 116.5 |
C5—C4—C3 | 110.7 (2) | C3GA—C4GA—C5GA | 116.5 (8) |
C5—C4—H41 | 109.5 | C3GA—C4GA—H4GA | 121.7 |
C3—C4—H41 | 109.5 | C5GA—C4GA—H4GA | 121.7 |
C5—C4—H42 | 109.5 | C4GA—C5GA—C6GA | 120.4 (8) |
C3—C4—H42 | 109.5 | C4GA—C5GA—H5GA | 119.8 |
H41—C4—H42 | 108.1 | C6GA—C5GA—H5GA | 119.8 |
C4—C5—C6 | 111.5 (2) | C5GA—C6GA—C1GA | 121.9 (7) |
C4—C5—H51 | 109.3 | C5GA—C6GA—C8GA | 120.7 (7) |
C6—C5—H51 | 109.3 | C1GA—C6GA—C8GA | 117.4 (6) |
C4—C5—H52 | 109.3 | C1GB—N1GB—H1A2 | 102.1 |
C6—C5—H52 | 109.3 | C1GB—N1GB—H1B1 | 125.6 |
H51—C5—H52 | 108.0 | C1GB—N1GB—H1B2 | 97.2 |
C5—C6—C1 | 112.7 (2) | H1B1—N1GB—H1B2 | 101.2 |
C5—C6—H61 | 109.0 | C6GB—C1GB—C2GB | 123.2 (6) |
C1—C6—H61 | 109.0 | C6GB—C1GB—N1GB | 122.2 (6) |
C5—C6—H62 | 109.0 | C2GB—C1GB—N1GB | 114.6 (4) |
C1—C6—H62 | 109.0 | C1GB—C2GB—C7GB | 123.5 |
H61—C6—H62 | 107.8 | C1GB—C2GB—C3GB | 118.1 |
C8—C7—C12 | 115.8 (2) | C7GB—C2GB—C3GB | 118.4 |
C8—C7—C1 | 121.0 (2) | C4GB—C3GB—C2GB | 112.8 (7) |
C12—C7—C1 | 123.1 (2) | C4GB—C3GB—H3GB | 123.6 |
C9—C8—C7 | 122.5 (2) | C2GB—C3GB—H3GB | 123.6 |
C9—C8—H8 | 118.7 | C5GB—C4GB—C3GB | 125.2 (10) |
C7—C8—H8 | 118.7 | C5GB—C4GB—H4GB | 117.4 |
C8—C9—C10 | 120.5 (3) | C3GB—C4GB—H4GB | 117.4 |
C8—C9—H9 | 119.8 | C4GB—C5GB—C6GB | 123.0 (10) |
C10—C9—H9 | 119.8 | C4GB—C5GB—H5GB | 118.5 |
O1—C10—C9 | 123.3 (2) | C6GB—C5GB—H5GB | 118.5 |
O1—C10—C11 | 118.0 (2) | C1GB—C6GB—C5GB | 117.6 (8) |
C9—C10—C11 | 118.7 (2) | C1GB—C6GB—C8GB | 120.5 (7) |
C12—C11—C10 | 120.3 (2) | C5GB—C6GB—C8GB | 121.9 (8) |
C12—C11—H11 | 119.9 | C2GB—C7GB—H7B1 | 109.5 |
C10—C11—H11 | 119.9 | C2GB—C7GB—H7B2 | 109.5 |
C11—C12—C7 | 122.2 (2) | H7B1—C7GB—H7B2 | 109.5 |
C11—C12—H12 | 118.9 | C2GB—C7GB—H7B3 | 109.5 |
C7—C12—H12 | 118.9 | H7B1—C7GB—H7B3 | 109.5 |
C14—C13—C18 | 115.8 (2) | H7B2—C7GB—H7B3 | 109.5 |
C14—C13—C1 | 124.3 (2) | C6GB—C8GB—H8B1 | 109.5 |
C18—C13—C1 | 119.9 (2) | C6GB—C8GB—H8B2 | 109.5 |
C13—C14—C15 | 122.2 (2) | H8B1—C8GB—H8B2 | 109.5 |
C13—C14—H14 | 118.9 | C6GB—C8GB—H8B3 | 109.5 |
C15—C14—H14 | 118.9 | H8B1—C8GB—H8B3 | 109.5 |
C16—C15—C14 | 119.8 (2) | H8B2—C8GB—H8B3 | 109.5 |
| | | |
C13—C1—C2—C3 | 175.2 (2) | C14—C15—C16—C17 | 0.1 (4) |
C6—C1—C2—C3 | 54.9 (3) | C14—C15—C16—O2 | −179.8 (3) |
C7—C1—C2—C3 | −66.5 (3) | C15—C16—C17—C18 | 0.7 (4) |
C1—C2—C3—C4 | −55.2 (3) | O2—C16—C17—C18 | −179.4 (3) |
C2—C3—C4—C5 | 53.1 (3) | C16—C17—C18—C13 | −0.9 (5) |
C3—C4—C5—C6 | −55.1 (3) | C14—C13—C18—C17 | 0.2 (4) |
C4—C5—C6—C1 | 58.9 (3) | C1—C13—C18—C17 | −179.0 (3) |
C13—C1—C6—C5 | −174.2 (2) | N1GA—C1GA—C2GA—C3GA | 176.6 (10) |
C7—C1—C6—C5 | 66.4 (3) | C6GA—C1GA—C2GA—C3GA | −1.2 (14) |
C2—C1—C6—C5 | −56.2 (3) | N1GA—C1GA—C2GA—C7GA | −2.0 (15) |
C13—C1—C7—C8 | −74.7 (3) | C6GA—C1GA—C2GA—C7GA | −179.8 (10) |
C6—C1—C7—C8 | 47.3 (3) | C1GA—C2GA—C3GA—C4GA | −0.4 (19) |
C2—C1—C7—C8 | 166.2 (2) | C7GA—C2GA—C3GA—C4GA | 178.2 (13) |
C13—C1—C7—C12 | 102.1 (3) | C2GA—C3GA—C4GA—C5GA | 1.8 (19) |
C6—C1—C7—C12 | −135.8 (2) | C3GA—C4GA—C5GA—C6GA | −1.6 (15) |
C2—C1—C7—C12 | −16.9 (3) | C4GA—C5GA—C6GA—C1GA | 0.0 (13) |
C12—C7—C8—C9 | 0.9 (4) | C4GA—C5GA—C6GA—C8GA | −179.3 (9) |
C1—C7—C8—C9 | 177.9 (2) | N1GA—C1GA—C6GA—C5GA | −176.4 (8) |
C7—C8—C9—C10 | −1.2 (4) | C2GA—C1GA—C6GA—C5GA | 1.4 (12) |
C8—C9—C10—O1 | −179.1 (2) | N1GA—C1GA—C6GA—C8GA | 2.9 (13) |
C8—C9—C10—C11 | 0.4 (4) | C2GA—C1GA—C6GA—C8GA | −179.3 (8) |
O1—C10—C11—C12 | −179.9 (2) | C6GB—C1GB—C2GB—C7GB | 178.1 (5) |
C9—C10—C11—C12 | 0.5 (4) | N1GB—C1GB—C2GB—C7GB | −1.0 (4) |
C10—C11—C12—C7 | −0.8 (4) | C6GB—C1GB—C2GB—C3GB | −0.4 (5) |
C8—C7—C12—C11 | 0.1 (4) | N1GB—C1GB—C2GB—C3GB | −179.5 (4) |
C1—C7—C12—C11 | −176.9 (2) | C1GB—C2GB—C3GB—C4GB | −0.7 (7) |
C6—C1—C13—C14 | 0.3 (3) | C7GB—C2GB—C3GB—C4GB | −179.3 (7) |
C7—C1—C13—C14 | 121.7 (3) | C2GB—C3GB—C4GB—C5GB | 1.4 (14) |
C2—C1—C13—C14 | −116.6 (3) | C3GB—C4GB—C5GB—C6GB | −1.0 (17) |
C6—C1—C13—C18 | 179.5 (2) | C2GB—C1GB—C6GB—C5GB | 1.0 (9) |
C7—C1—C13—C18 | −59.1 (3) | N1GB—C1GB—C6GB—C5GB | 180.0 (7) |
C2—C1—C13—C18 | 62.7 (3) | C2GB—C1GB—C6GB—C8GB | −179.3 (5) |
C18—C13—C14—C15 | 0.6 (4) | N1GB—C1GB—C6GB—C8GB | −0.3 (10) |
C1—C13—C14—C15 | 179.9 (2) | C4GB—C5GB—C6GB—C1GB | −0.3 (13) |
C13—C14—C15—C16 | −0.8 (4) | C4GB—C5GB—C6GB—C8GB | 179.9 (9) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1GB | 0.97 | 1.77 | 2.642 (6) | 148 |
O1—H1···N1GA | 0.97 | 1.97 | 2.896 (7) | 160 |
O2—H2···O1i | 0.98 | 1.78 | 2.757 (3) | 172 |
N1GA—H1A2···O2ii | 0.96 | 2.28 | 3.209 (7) | 162 |
N1GB—H1B2···O2ii | 0.96 | 2.29 | 3.060 (6) | 136 |
Symmetry codes: (i) x, y+1, z; (ii) x+1, y−1, z. |
(dc26x1.5) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 2,6-xylidine
top
Crystal data top
C18H20O2/1.5(C8H11N) | Z = 2 |
Mr = 450.11 | F(000) = 486 |
Triclinic, P1 | Dx = 1.191 Mg m−3 Dm = N/A Mg m−3 Dm measured by not measured |
a = 7.8594 (3) Å | Melting point: 363.65K for guest release onset temp. and 463.15K for host melting K |
b = 10.015 (1) Å | Mo Kα radiation, λ = 0.71069 Å |
c = 17.169 (1) Å | µ = 0.07 mm−1 |
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 tube | Rint = 0.017 |
Graphite monochromator | θmax = 25.6°, θmin = 2.7° |
1° φ scans and ω scans | h = −6→9 |
6193 measured reflections | k = −12→11 |
4593 independent reflections | l = −20→20 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.056 | H 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 reflections | Δρmax = 0.42 e Å−3 |
344 parameters | Δρmin = −0.18 e Å−3 |
6 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.9230 (2) | 0.59543 (15) | 0.20898 (9) | 0.0367 (4) | |
C7 | 0.5408 (3) | 0.7382 (2) | 0.38512 (12) | 0.0254 (5) | |
O2 | 0.7771 (3) | 0.63742 (18) | 0.74928 (10) | 0.0546 (6) | |
C8 | 0.6336 (3) | 0.8265 (2) | 0.34196 (13) | 0.0288 (5) | |
H8 | 0.6106 | 0.9197 | 0.3537 | 0.035* | |
N1GA | 1.0563 (3) | 0.7893 (2) | 0.10180 (13) | 0.0378 (5) | |
C1 | 0.4117 (3) | 0.7841 (2) | 0.45450 (12) | 0.0260 (5) | |
C14 | 0.4262 (3) | 0.7742 (2) | 0.60361 (13) | 0.0318 (6) | |
H14 | 0.3006 | 0.8229 | 0.6029 | 0.038* | |
C13 | 0.5163 (3) | 0.7407 (2) | 0.53245 (13) | 0.0259 (5) | |
C10 | 0.7946 (3) | 0.6476 (2) | 0.26519 (12) | 0.0266 (5) | |
C1GA | 1.0165 (3) | 0.9332 (2) | 0.11471 (13) | 0.0317 (6) | |
C11 | 0.7033 (3) | 0.5583 (2) | 0.30602 (13) | 0.0311 (6) | |
H11 | 0.7263 | 0.4654 | 0.2939 | 0.037* | |
C3 | 0.1936 (3) | 0.9999 (2) | 0.36880 (14) | 0.0346 (6) | |
H31 | 0.1324 | 1.1042 | 0.3641 | 0.042* | |
H32 | 0.2662 | 0.9829 | 0.3196 | 0.042* | |
C9 | 0.7585 (3) | 0.7832 (2) | 0.28235 (13) | 0.0294 (5) | |
H9 | 0.8187 | 0.8465 | 0.2536 | 0.035* | |
C2GA | 1.1429 (3) | 0.9729 (2) | 0.14917 (13) | 0.0329 (6) | |
C18 | 0.6987 (3) | 0.6692 (2) | 0.53724 (13) | 0.0306 (6) | |
H18 | 0.7649 | 0.6447 | 0.4903 | 0.037* | |
C12 | 0.5779 (3) | 0.6036 (2) | 0.36479 (13) | 0.0283 (5) | |
H12 | 0.5153 | 0.5409 | 0.3921 | 0.034* | |
C2 | 0.3177 (3) | 0.9483 (2) | 0.43995 (13) | 0.0307 (6) | |
H21 | 0.2466 | 0.9753 | 0.4881 | 0.037* | |
H22 | 0.4105 | 0.9974 | 0.4309 | 0.037* | |
C17 | 0.7887 (3) | 0.6318 (2) | 0.60860 (14) | 0.0354 (6) | |
H17 | 0.9140 | 0.5818 | 0.6100 | 0.042* | |
C6 | 0.2603 (3) | 0.7130 (2) | 0.46456 (13) | 0.0304 (6) | |
H61 | 0.3155 | 0.6077 | 0.4726 | 0.036* | |
H62 | 0.1869 | 0.7371 | 0.5127 | 0.036* | |
C16 | 0.6954 (4) | 0.6675 (2) | 0.67722 (14) | 0.0379 (6) | |
C15 | 0.5134 (3) | 0.7389 (2) | 0.67462 (14) | 0.0365 (6) | |
H15 | 0.4482 | 0.7638 | 0.7217 | 0.044* | |
C5 | 0.1376 (3) | 0.7607 (2) | 0.39329 (14) | 0.0345 (6) | |
H51 | 0.2081 | 0.7295 | 0.3458 | 0.041* | |
H52 | 0.0416 | 0.7149 | 0.4037 | 0.041* | |
C6GA | 0.8461 (3) | 1.0303 (3) | 0.09581 (14) | 0.0396 (6) | |
C4 | 0.0534 (3) | 0.9226 (2) | 0.37746 (15) | 0.0393 (6) | |
H41 | −0.0311 | 0.9519 | 0.4217 | 0.047* | |
H42 | −0.0163 | 0.9514 | 0.3282 | 0.047* | |
C7GA | 1.3255 (3) | 0.8678 (3) | 0.16988 (15) | 0.0449 (7) | |
H7A1 | 1.3120 | 0.7860 | 0.2087 | 0.067* | |
H7A2 | 1.3966 | 0.9146 | 0.1926 | 0.067* | |
H7A3 | 1.3868 | 0.8344 | 0.1218 | 0.067* | |
C3GA | 1.0982 (4) | 1.1127 (3) | 0.16304 (14) | 0.0463 (7) | |
H3GA | 1.1839 | 1.1416 | 0.1858 | 0.056* | |
C5GA | 0.8068 (4) | 1.1687 (3) | 0.11109 (16) | 0.0560 (8) | |
H5GA | 0.6920 | 1.2362 | 0.0984 | 0.067* | |
C8GA | 0.7094 (4) | 0.9854 (3) | 0.06041 (17) | 0.0626 (9) | |
H8A1 | 0.5982 | 1.0661 | 0.0517 | 0.094* | |
H8A2 | 0.6845 | 0.9053 | 0.0968 | 0.094* | |
H8A3 | 0.7562 | 0.9555 | 0.0096 | 0.094* | |
C4GA | 0.9314 (5) | 1.2096 (3) | 0.14425 (17) | 0.0593 (9) | |
H4GA | 0.9024 | 1.3046 | 0.1542 | 0.071* | |
H1 | 0.969 (4) | 0.667 (2) | 0.1772 (14) | 0.080 (10)* | |
H2 | 0.896 (3) | 0.564 (2) | 0.7531 (17) | 0.092 (11)* | |
H1A1 | 1.181 (3) | 0.738 (3) | 0.1010 (17) | 0.072 (10)* | |
H1A2 | 1.005 (4) | 0.784 (3) | 0.0557 (15) | 0.077 (10)* | |
N1GB | 1.4477 (3) | 0.5150 (2) | 0.12078 (13) | 0.0429 (6) | 0.50 |
C6GB | 1.6201 (3) | 0.5521 (2) | −0.00147 (14) | 0.0336 (6) | 0.50 |
C1GB | 1.5132 (7) | 0.4911 (4) | −0.0374 (3) | 0.0308 (11) | 0.50 |
C3GB | 1.3440 (7) | 0.4510 (5) | 0.0852 (3) | 0.0400 (13) | 0.50 |
C5GB | 1.5824 (7) | 0.5539 (5) | 0.0834 (3) | 0.0415 (13) | 0.50 |
C7GB | 1.7399 (8) | 0.6205 (5) | 0.0355 (3) | 0.0524 (15) | 0.50 |
C8GB | 1.7650 (7) | 0.6009 (5) | −0.0434 (4) | 0.0514 (14) | 0.50 |
C4GB | 1.4477 (3) | 0.5150 (2) | 0.12078 (13) | 0.0429 (6) | 0.50 |
C2GB | 1.6201 (3) | 0.5521 (2) | −0.00147 (14) | 0.0336 (6) | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0377 (10) | 0.0366 (9) | 0.0325 (10) | −0.0102 (8) | 0.0081 (8) | −0.0042 (7) |
C7 | 0.0258 (13) | 0.0258 (11) | 0.0253 (13) | −0.0098 (10) | −0.0033 (10) | −0.0021 (9) |
O2 | 0.0690 (14) | 0.0461 (11) | 0.0411 (11) | 0.0012 (10) | −0.0237 (10) | −0.0132 (8) |
C8 | 0.0302 (14) | 0.0276 (11) | 0.0329 (14) | −0.0146 (10) | −0.0019 (11) | −0.0053 (10) |
N1GA | 0.0437 (15) | 0.0398 (12) | 0.0336 (13) | −0.0200 (11) | 0.0028 (11) | −0.0048 (9) |
C1 | 0.0263 (13) | 0.0256 (11) | 0.0269 (13) | −0.0096 (10) | −0.0003 (10) | −0.0043 (9) |
C14 | 0.0353 (14) | 0.0256 (12) | 0.0329 (14) | −0.0079 (10) | −0.0007 (11) | −0.0041 (10) |
C13 | 0.0296 (14) | 0.0215 (11) | 0.0295 (13) | −0.0116 (10) | −0.0007 (10) | −0.0051 (9) |
C10 | 0.0238 (13) | 0.0304 (12) | 0.0243 (13) | −0.0077 (10) | −0.0007 (10) | −0.0029 (10) |
C1GA | 0.0358 (15) | 0.0340 (13) | 0.0230 (13) | −0.0125 (11) | 0.0060 (11) | 0.0002 (10) |
C11 | 0.0358 (14) | 0.0267 (11) | 0.0314 (14) | −0.0108 (10) | 0.0006 (11) | −0.0055 (10) |
C3 | 0.0340 (14) | 0.0297 (12) | 0.0370 (15) | −0.0057 (11) | −0.0029 (11) | −0.0052 (10) |
C9 | 0.0279 (13) | 0.0310 (12) | 0.0313 (14) | −0.0147 (10) | −0.0010 (11) | −0.0008 (10) |
C2GA | 0.0349 (15) | 0.0372 (13) | 0.0259 (13) | −0.0127 (11) | 0.0035 (11) | −0.0034 (10) |
C18 | 0.0330 (15) | 0.0273 (11) | 0.0327 (14) | −0.0107 (10) | −0.0004 (11) | −0.0063 (10) |
C12 | 0.0300 (13) | 0.0268 (12) | 0.0300 (13) | −0.0141 (10) | 0.0011 (11) | −0.0014 (9) |
C2 | 0.0335 (14) | 0.0280 (12) | 0.0311 (14) | −0.0101 (10) | 0.0000 (11) | −0.0060 (9) |
C17 | 0.0360 (15) | 0.0287 (12) | 0.0422 (16) | −0.0085 (10) | −0.0092 (12) | −0.0073 (11) |
C6 | 0.0297 (14) | 0.0303 (12) | 0.0320 (14) | −0.0122 (10) | 0.0042 (11) | −0.0049 (10) |
C16 | 0.0564 (18) | 0.0265 (12) | 0.0303 (15) | −0.0087 (12) | −0.0130 (13) | −0.0061 (10) |
C15 | 0.0496 (17) | 0.0267 (12) | 0.0298 (14) | −0.0061 (11) | −0.0023 (12) | −0.0063 (10) |
C5 | 0.0266 (13) | 0.0389 (13) | 0.0402 (15) | −0.0141 (10) | −0.0003 (11) | −0.0060 (10) |
C6GA | 0.0320 (15) | 0.0512 (16) | 0.0298 (15) | −0.0115 (12) | 0.0009 (11) | 0.0034 (11) |
C4 | 0.0329 (15) | 0.0416 (14) | 0.0396 (16) | −0.0064 (11) | −0.0040 (12) | −0.0056 (11) |
C7GA | 0.0351 (16) | 0.0553 (16) | 0.0453 (17) | −0.0125 (13) | −0.0022 (12) | −0.0136 (12) |
C3GA | 0.0635 (19) | 0.0404 (15) | 0.0360 (16) | −0.0181 (14) | −0.0027 (13) | −0.0053 (11) |
C5GA | 0.0523 (19) | 0.0465 (17) | 0.0438 (18) | 0.0104 (14) | −0.0010 (15) | 0.0082 (13) |
C8GA | 0.0433 (18) | 0.086 (2) | 0.0500 (19) | −0.0215 (16) | −0.0085 (15) | 0.0130 (15) |
C4GA | 0.080 (2) | 0.0351 (15) | 0.0510 (19) | −0.0036 (16) | −0.0029 (17) | −0.0046 (13) |
N1GB | 0.0477 (16) | 0.0431 (13) | 0.0350 (14) | −0.0063 (12) | 0.0005 (12) | −0.0140 (11) |
C6GB | 0.0355 (15) | 0.0258 (12) | 0.0348 (15) | −0.0016 (11) | −0.0039 (12) | −0.0064 (10) |
C1GB | 0.037 (3) | 0.024 (2) | 0.027 (3) | −0.006 (2) | −0.003 (2) | 0.000 (2) |
C3GB | 0.050 (3) | 0.028 (2) | 0.038 (3) | −0.008 (2) | −0.002 (3) | −0.003 (2) |
C5GB | 0.043 (3) | 0.026 (2) | 0.050 (3) | −0.002 (2) | −0.009 (3) | −0.003 (2) |
C7GB | 0.056 (4) | 0.041 (3) | 0.066 (4) | −0.011 (3) | −0.024 (3) | −0.018 (3) |
C8GB | 0.044 (4) | 0.051 (3) | 0.064 (4) | −0.022 (3) | 0.004 (3) | −0.011 (3) |
C4GB | 0.0477 (16) | 0.0431 (13) | 0.0350 (14) | −0.0063 (12) | 0.0005 (12) | −0.0140 (11) |
C2GB | 0.0355 (15) | 0.0258 (12) | 0.0348 (15) | −0.0016 (11) | −0.0039 (12) | −0.0064 (10) |
Geometric parameters (Å, º) top
O1—C10 | 1.383 (2) | C15—H15 | 0.9500 |
O1—H1 | 0.963 (14) | C5—C4 | 1.520 (3) |
C7—C8 | 1.391 (3) | C5—H51 | 0.9900 |
C7—C12 | 1.391 (3) | C5—H52 | 0.9900 |
C7—C1 | 1.538 (3) | C6GA—C5GA | 1.392 (4) |
O2—C16 | 1.378 (3) | C6GA—C8GA | 1.501 (4) |
O2—H2 | 0.985 (14) | C4—H41 | 0.9900 |
C8—C9 | 1.388 (3) | C4—H42 | 0.9900 |
C8—H8 | 0.9500 | C7GA—H7A1 | 0.9800 |
N1GA—C1GA | 1.430 (3) | C7GA—H7A2 | 0.9800 |
N1GA—H1A1 | 0.95 (2) | C7GA—H7A3 | 0.9800 |
N1GA—H1A2 | 0.93 (2) | C3GA—C4GA | 1.378 (4) |
C1—C13 | 1.545 (3) | C3GA—H3GA | 0.9500 |
C1—C2 | 1.550 (3) | C5GA—C4GA | 1.376 (4) |
C1—C6 | 1.554 (3) | C5GA—H5GA | 0.9500 |
C14—C15 | 1.378 (3) | C8GA—H8A1 | 0.9800 |
C14—C13 | 1.402 (3) | C8GA—H8A2 | 0.9800 |
C14—H14 | 0.9500 | C8GA—H8A3 | 0.9800 |
C13—C18 | 1.383 (3) | C4GA—H4GA | 0.9500 |
C10—C11 | 1.376 (3) | N1GB—C5GB | 1.318 (6) |
C10—C9 | 1.380 (3) | N1GB—C3GB | 1.421 (6) |
C1GA—C2GA | 1.393 (3) | N1GB—C1GBi | 1.448 (5) |
C1GA—C6GA | 1.400 (3) | C6GB—C1GBi | 1.339 (5) |
C11—C12 | 1.384 (3) | C6GB—C1GB | 1.422 (6) |
C11—H11 | 0.9500 | C6GB—C3GBi | 1.446 (5) |
C3—C4 | 1.521 (3) | C6GB—C8GB | 1.462 (6) |
C3—C2 | 1.531 (3) | C6GB—C5GB | 1.465 (6) |
C3—H31 | 0.9900 | C6GB—C7GB | 1.563 (6) |
C3—H32 | 0.9900 | C1GB—C1GBi | 1.319 (9) |
C9—H9 | 0.9500 | C1GB—C2GBi | 1.339 (5) |
C2GA—C3GA | 1.392 (3) | C1GB—C6GBi | 1.339 (5) |
C2GA—C7GA | 1.504 (3) | C1GB—C5GBi | 1.359 (7) |
C18—C17 | 1.393 (3) | C1GB—C4GBi | 1.448 (5) |
C18—H18 | 0.9500 | C1GB—N1GBi | 1.448 (5) |
C12—H12 | 0.9500 | C1GB—C3GBi | 1.533 (7) |
C2—H21 | 0.9900 | C3GB—C8GBi | 1.433 (8) |
C2—H22 | 0.9900 | C3GB—C2GBi | 1.446 (5) |
C17—C16 | 1.379 (3) | C3GB—C6GBi | 1.446 (5) |
C17—H17 | 0.9500 | C3GB—C1GBi | 1.533 (7) |
C6—C5 | 1.527 (3) | C5GB—C1GBi | 1.359 (7) |
C6—H61 | 0.9900 | C5GB—C7GB | 1.674 (8) |
C6—H62 | 0.9900 | C7GB—C8GB | 1.395 (8) |
C16—C15 | 1.378 (3) | C8GB—C3GBi | 1.433 (8) |
| | | |
C10—O1—H1 | 113.5 (17) | H7A1—C7GA—H7A2 | 109.5 |
C8—C7—C12 | 116.41 (19) | C2GA—C7GA—H7A3 | 109.5 |
C8—C7—C1 | 121.68 (18) | H7A1—C7GA—H7A3 | 109.5 |
C12—C7—C1 | 121.83 (19) | H7A2—C7GA—H7A3 | 109.5 |
C16—O2—H2 | 115.3 (18) | C4GA—C3GA—C2GA | 120.9 (3) |
C9—C8—C7 | 122.32 (19) | C4GA—C3GA—H3GA | 119.6 |
C9—C8—H8 | 118.8 | C2GA—C3GA—H3GA | 119.6 |
C7—C8—H8 | 118.8 | C4GA—C5GA—C6GA | 121.1 (2) |
C1GA—N1GA—H1A1 | 113.7 (18) | C4GA—C5GA—H5GA | 119.4 |
C1GA—N1GA—H1A2 | 112.4 (18) | C6GA—C5GA—H5GA | 119.4 |
H1A1—N1GA—H1A2 | 110 (3) | C6GA—C8GA—H8A1 | 109.5 |
C7—C1—C13 | 109.93 (17) | C6GA—C8GA—H8A2 | 109.5 |
C7—C1—C2 | 111.22 (17) | H8A1—C8GA—H8A2 | 109.5 |
C13—C1—C2 | 108.86 (15) | C6GA—C8GA—H8A3 | 109.5 |
C7—C1—C6 | 111.09 (16) | H8A1—C8GA—H8A3 | 109.5 |
C13—C1—C6 | 108.95 (17) | H8A2—C8GA—H8A3 | 109.5 |
C2—C1—C6 | 106.69 (16) | C5GA—C4GA—C3GA | 120.0 (2) |
C15—C14—C13 | 122.3 (2) | C5GA—C4GA—H4GA | 120.0 |
C15—C14—H14 | 118.8 | C3GA—C4GA—H4GA | 120.0 |
C13—C14—H14 | 118.8 | C5GB—N1GB—C3GB | 122.9 (3) |
C18—C13—C14 | 116.2 (2) | C5GB—N1GB—C1GBi | 58.6 (3) |
C18—C13—C1 | 123.73 (19) | C3GB—N1GB—C1GBi | 64.6 (3) |
C14—C13—C1 | 120.02 (18) | C1GBi—C6GB—C1GB | 57.0 (4) |
C11—C10—C9 | 119.6 (2) | C1GBi—C6GB—C3GBi | 121.5 (4) |
C11—C10—O1 | 117.89 (18) | C1GB—C6GB—C3GBi | 64.6 (3) |
C9—C10—O1 | 122.5 (2) | C1GBi—C6GB—C8GB | 179.3 (3) |
C2GA—C1GA—C6GA | 121.0 (2) | C1GB—C6GB—C8GB | 123.5 (4) |
C2GA—C1GA—N1GA | 120.1 (2) | C3GBi—C6GB—C8GB | 59.0 (3) |
C6GA—C1GA—N1GA | 118.8 (2) | C1GBi—C6GB—C5GB | 57.8 (3) |
C10—C11—C12 | 120.1 (2) | C1GB—C6GB—C5GB | 114.6 (4) |
C10—C11—H11 | 119.9 | C3GBi—C6GB—C5GB | 179.2 (4) |
C12—C11—H11 | 119.9 | C8GB—C6GB—C5GB | 121.7 (4) |
C4—C3—C2 | 111.45 (19) | C1GBi—C6GB—C7GB | 124.6 (3) |
C4—C3—H31 | 109.3 | C1GB—C6GB—C7GB | 178.3 (4) |
C2—C3—H31 | 109.3 | C3GBi—C6GB—C7GB | 113.7 (4) |
C4—C3—H32 | 109.3 | C8GB—C6GB—C7GB | 54.8 (3) |
C2—C3—H32 | 109.3 | C5GB—C6GB—C7GB | 67.0 (3) |
H31—C3—H32 | 108.0 | C1GBi—C1GB—C2GBi | 64.7 (4) |
C10—C9—C8 | 119.5 (2) | C1GBi—C1GB—C6GBi | 64.7 (4) |
C10—C9—H9 | 120.2 | C2GBi—C1GB—C6GBi | 0.0 (3) |
C8—C9—H9 | 120.2 | C1GBi—C1GB—C5GBi | 130.2 (7) |
C3GA—C2GA—C1GA | 118.7 (2) | C2GBi—C1GB—C5GBi | 65.7 (4) |
C3GA—C2GA—C7GA | 120.5 (2) | C6GBi—C1GB—C5GBi | 65.7 (4) |
C1GA—C2GA—C7GA | 120.8 (2) | C1GBi—C1GB—C6GB | 58.3 (4) |
C13—C18—C17 | 122.2 (2) | C2GBi—C1GB—C6GB | 123.0 (4) |
C13—C18—H18 | 118.9 | C6GBi—C1GB—C6GB | 123.0 (4) |
C17—C18—H18 | 118.9 | C5GBi—C1GB—C6GB | 170.3 (5) |
C11—C12—C7 | 122.0 (2) | C1GBi—C1GB—C4GBi | 173.1 (6) |
C11—C12—H12 | 119.0 | C2GBi—C1GB—C4GBi | 121.6 (4) |
C7—C12—H12 | 119.0 | C6GBi—C1GB—C4GBi | 121.6 (4) |
C3—C2—C1 | 112.85 (17) | C5GBi—C1GB—C4GBi | 55.9 (3) |
C3—C2—H21 | 109.0 | C6GB—C1GB—C4GBi | 115.3 (4) |
C1—C2—H21 | 109.0 | C1GBi—C1GB—N1GBi | 173.1 (6) |
C3—C2—H22 | 109.0 | C2GBi—C1GB—N1GBi | 121.6 (4) |
C1—C2—H22 | 109.0 | C6GBi—C1GB—N1GBi | 121.6 (4) |
H21—C2—H22 | 107.8 | C5GBi—C1GB—N1GBi | 55.9 (3) |
C16—C17—C18 | 119.8 (2) | C6GB—C1GB—N1GBi | 115.3 (4) |
C16—C17—H17 | 120.1 | C4GBi—C1GB—N1GBi | 0.00 (4) |
C18—C17—H17 | 120.1 | C1GBi—C1GB—C3GBi | 116.7 (6) |
C5—C6—C1 | 112.97 (18) | C2GBi—C1GB—C3GBi | 176.1 (4) |
C5—C6—H61 | 109.0 | C6GBi—C1GB—C3GBi | 176.1 (4) |
C1—C6—H61 | 109.0 | C5GBi—C1GB—C3GBi | 112.5 (4) |
C5—C6—H62 | 109.0 | C6GB—C1GB—C3GBi | 58.4 (3) |
C1—C6—H62 | 109.0 | C4GBi—C1GB—C3GBi | 56.9 (3) |
H61—C6—H62 | 107.8 | N1GBi—C1GB—C3GBi | 56.9 (3) |
O2—C16—C15 | 117.7 (2) | N1GB—C3GB—C8GBi | 174.3 (5) |
O2—C16—C17 | 122.7 (2) | N1GB—C3GB—C2GBi | 115.5 (4) |
C15—C16—C17 | 119.6 (2) | C8GBi—C3GB—C2GBi | 61.1 (3) |
C14—C15—C16 | 119.9 (2) | N1GB—C3GB—C6GBi | 115.5 (4) |
C14—C15—H15 | 120.1 | C8GBi—C3GB—C6GBi | 61.1 (3) |
C16—C15—H15 | 120.1 | C2GBi—C3GB—C6GBi | 0.00 (17) |
C4—C5—C6 | 110.81 (18) | N1GB—C3GB—C1GBi | 58.6 (3) |
C4—C5—H51 | 109.5 | C8GBi—C3GB—C1GBi | 117.9 (4) |
C6—C5—H51 | 109.5 | C2GBi—C3GB—C1GBi | 56.9 (3) |
C4—C5—H52 | 109.5 | C6GBi—C3GB—C1GBi | 56.9 (3) |
C6—C5—H52 | 109.5 | N1GB—C5GB—C1GBi | 65.5 (3) |
H51—C5—H52 | 108.1 | N1GB—C5GB—C6GB | 121.9 (4) |
C5GA—C6GA—C1GA | 118.3 (2) | C1GBi—C5GB—C6GB | 56.5 (3) |
C5GA—C6GA—C8GA | 121.1 (2) | N1GB—C5GB—C7GB | 174.2 (4) |
C1GA—C6GA—C8GA | 120.6 (2) | C1GBi—C5GB—C7GB | 115.6 (4) |
C5—C4—C3 | 112.16 (19) | C6GB—C5GB—C7GB | 59.3 (3) |
C5—C4—H41 | 109.2 | C8GB—C7GB—C6GB | 58.9 (3) |
C3—C4—H41 | 109.2 | C8GB—C7GB—C5GB | 112.5 (4) |
C5—C4—H42 | 109.2 | C6GB—C7GB—C5GB | 53.7 (3) |
C3—C4—H42 | 109.2 | C7GB—C8GB—C3GBi | 126.0 (5) |
H41—C4—H42 | 107.9 | C7GB—C8GB—C6GB | 66.3 (4) |
C2GA—C7GA—H7A1 | 109.5 | C3GBi—C8GB—C6GB | 59.9 (3) |
C2GA—C7GA—H7A2 | 109.5 | | |
| | | |
C12—C7—C8—C9 | −0.8 (3) | C7GB—C6GB—C1GB—C6GBi | −168 (10) |
C1—C7—C8—C9 | 176.06 (19) | C1GBi—C6GB—C1GB—C5GBi | 153 (3) |
C8—C7—C1—C13 | −88.0 (2) | C3GBi—C6GB—C1GB—C5GBi | −23 (2) |
C12—C7—C1—C13 | 88.7 (2) | C8GB—C6GB—C1GB—C5GBi | −27 (3) |
C8—C7—C1—C2 | 32.7 (3) | C5GB—C6GB—C1GB—C5GBi | 157 (2) |
C12—C7—C1—C2 | −150.7 (2) | C7GB—C6GB—C1GB—C5GBi | −16 (12) |
C8—C7—C1—C6 | 151.4 (2) | C1GBi—C6GB—C1GB—C4GBi | 177.1 (6) |
C12—C7—C1—C6 | −32.0 (3) | C3GBi—C6GB—C1GB—C4GBi | 1.4 (3) |
C15—C14—C13—C18 | 0.3 (3) | C8GB—C6GB—C1GB—C4GBi | −2.3 (5) |
C15—C14—C13—C1 | −179.49 (19) | C5GB—C6GB—C1GB—C4GBi | −178.4 (3) |
C7—C1—C13—C18 | −0.9 (3) | C7GB—C6GB—C1GB—C4GBi | 9 (11) |
C2—C1—C13—C18 | −123.0 (2) | C1GBi—C6GB—C1GB—N1GBi | 177.1 (6) |
C6—C1—C13—C18 | 121.0 (2) | C3GBi—C6GB—C1GB—N1GBi | 1.4 (3) |
C7—C1—C13—C14 | 178.84 (18) | C8GB—C6GB—C1GB—N1GBi | −2.3 (5) |
C2—C1—C13—C14 | 56.8 (2) | C5GB—C6GB—C1GB—N1GBi | −178.4 (3) |
C6—C1—C13—C14 | −59.2 (2) | C7GB—C6GB—C1GB—N1GBi | 9 (11) |
C9—C10—C11—C12 | −1.0 (3) | C1GBi—C6GB—C1GB—C3GBi | 175.7 (4) |
O1—C10—C11—C12 | 177.78 (19) | C8GB—C6GB—C1GB—C3GBi | −3.7 (4) |
C11—C10—C9—C8 | 1.6 (3) | C5GB—C6GB—C1GB—C3GBi | −179.8 (3) |
O1—C10—C9—C8 | −177.13 (19) | C7GB—C6GB—C1GB—C3GBi | 7 (10) |
C7—C8—C9—C10 | −0.7 (3) | C5GB—N1GB—C3GB—C8GBi | −59 (5) |
C6GA—C1GA—C2GA—C3GA | −1.4 (3) | C1GBi—N1GB—C3GB—C8GBi | −53 (5) |
N1GA—C1GA—C2GA—C3GA | −178.2 (2) | C5GB—N1GB—C3GB—C2GBi | −7.8 (5) |
C6GA—C1GA—C2GA—C7GA | 179.6 (2) | C1GBi—N1GB—C3GB—C2GBi | −1.4 (3) |
N1GA—C1GA—C2GA—C7GA | 2.8 (3) | C5GB—N1GB—C3GB—C6GBi | −7.8 (5) |
C14—C13—C18—C17 | 0.2 (3) | C1GBi—N1GB—C3GB—C6GBi | −1.4 (3) |
C1—C13—C18—C17 | 179.95 (19) | C5GB—N1GB—C3GB—C1GBi | −6.4 (4) |
C10—C11—C12—C7 | −0.6 (3) | C3GB—N1GB—C5GB—C1GBi | 6.7 (4) |
C8—C7—C12—C11 | 1.4 (3) | C3GB—N1GB—C5GB—C6GB | 8.5 (5) |
C1—C7—C12—C11 | −175.4 (2) | C1GBi—N1GB—C5GB—C6GB | 1.8 (3) |
C4—C3—C2—C1 | 56.0 (2) | C3GB—N1GB—C5GB—C7GB | 109 (5) |
C7—C1—C2—C3 | 65.0 (2) | C1GBi—N1GB—C5GB—C7GB | 102 (5) |
C13—C1—C2—C3 | −173.71 (18) | C1GBi—C6GB—C5GB—N1GB | −1.9 (3) |
C6—C1—C2—C3 | −56.3 (2) | C1GB—C6GB—C5GB—N1GB | −6.4 (5) |
C13—C18—C17—C16 | −0.6 (3) | C3GBi—C6GB—C5GB—N1GB | −20 (26) |
C7—C1—C6—C5 | −64.2 (2) | C8GB—C6GB—C5GB—N1GB | 177.4 (3) |
C13—C1—C6—C5 | 174.57 (16) | C7GB—C6GB—C5GB—N1GB | 173.3 (4) |
C2—C1—C6—C5 | 57.2 (2) | C1GB—C6GB—C5GB—C1GBi | −4.5 (4) |
C18—C17—C16—O2 | −178.1 (2) | C3GBi—C6GB—C5GB—C1GBi | −18 (26) |
C18—C17—C16—C15 | 0.6 (3) | C8GB—C6GB—C5GB—C1GBi | 179.4 (4) |
C13—C14—C15—C16 | −0.3 (3) | C7GB—C6GB—C5GB—C1GBi | 175.3 (3) |
O2—C16—C15—C14 | 178.6 (2) | C1GBi—C6GB—C5GB—C7GB | −175.3 (3) |
C17—C16—C15—C14 | −0.1 (3) | C1GB—C6GB—C5GB—C7GB | −179.8 (3) |
C1—C6—C5—C4 | −57.2 (2) | C3GBi—C6GB—C5GB—C7GB | 167 (26) |
C2GA—C1GA—C6GA—C5GA | 1.1 (3) | C8GB—C6GB—C5GB—C7GB | 4.1 (4) |
N1GA—C1GA—C6GA—C5GA | 177.9 (2) | C1GBi—C6GB—C7GB—C8GB | −179.4 (4) |
C2GA—C1GA—C6GA—C8GA | −178.6 (2) | C1GB—C6GB—C7GB—C8GB | −11 (10) |
N1GA—C1GA—C6GA—C8GA | −1.8 (3) | C3GBi—C6GB—C7GB—C8GB | −4.1 (4) |
C6—C5—C4—C3 | 53.7 (3) | C5GB—C6GB—C7GB—C8GB | 175.7 (4) |
C2—C3—C4—C5 | −53.2 (2) | C1GBi—C6GB—C7GB—C5GB | 4.9 (4) |
C1GA—C2GA—C3GA—C4GA | 1.0 (4) | C1GB—C6GB—C7GB—C5GB | 173 (10) |
C7GA—C2GA—C3GA—C4GA | −180.0 (2) | C3GBi—C6GB—C7GB—C5GB | −179.8 (3) |
C1GA—C6GA—C5GA—C4GA | −0.3 (4) | C8GB—C6GB—C7GB—C5GB | −175.7 (4) |
C8GA—C6GA—C5GA—C4GA | 179.4 (3) | N1GB—C5GB—C7GB—C8GB | −107 (5) |
C6GA—C5GA—C4GA—C3GA | −0.1 (4) | C1GBi—C5GB—C7GB—C8GB | −8.3 (6) |
C2GA—C3GA—C4GA—C5GA | −0.2 (4) | C6GB—C5GB—C7GB—C8GB | −3.9 (4) |
C3GBi—C6GB—C1GB—C1GBi | −175.7 (4) | N1GB—C5GB—C7GB—C6GB | −103 (5) |
C8GB—C6GB—C1GB—C1GBi | −179.4 (4) | C1GBi—C5GB—C7GB—C6GB | −4.4 (3) |
C5GB—C6GB—C1GB—C1GBi | 4.5 (4) | C6GB—C7GB—C8GB—C3GBi | 4.6 (5) |
C7GB—C6GB—C1GB—C1GBi | −168 (10) | C5GB—C7GB—C8GB—C3GBi | 8.4 (7) |
C1GBi—C6GB—C1GB—C2GBi | 0.000 (1) | C5GB—C7GB—C8GB—C6GB | 3.7 (3) |
C3GBi—C6GB—C1GB—C2GBi | −175.7 (4) | C1GBi—C6GB—C8GB—C7GB | 42 (31) |
C8GB—C6GB—C1GB—C2GBi | −179.4 (4) | C1GB—C6GB—C8GB—C7GB | 179.6 (4) |
C5GB—C6GB—C1GB—C2GBi | 4.5 (4) | C3GBi—C6GB—C8GB—C7GB | 175.7 (4) |
C7GB—C6GB—C1GB—C2GBi | −168 (10) | C5GB—C6GB—C8GB—C7GB | −4.6 (4) |
C1GBi—C6GB—C1GB—C6GBi | 0.000 (1) | C1GBi—C6GB—C8GB—C3GBi | −133 (31) |
C3GBi—C6GB—C1GB—C6GBi | −175.7 (4) | C1GB—C6GB—C8GB—C3GBi | 3.9 (4) |
C8GB—C6GB—C1GB—C6GBi | −179.4 (4) | C5GB—C6GB—C8GB—C3GBi | 179.7 (3) |
C5GB—C6GB—C1GB—C6GBi | 4.5 (4) | C7GB—C6GB—C8GB—C3GBi | −175.7 (4) |
Symmetry code: (i) −x+3, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N1GA | 0.96 (1) | 1.85 (1) | 2.804 (3) | 170 (3) |
O2—H2···O1ii | 0.99 (1) | 1.81 (2) | 2.759 (2) | 160 (3) |
N1GA—H1A1···N1GB | 0.95 (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 = 571.29 | F(000) = 1236 |
Triclinic, P1 | Dx = 1.166 Mg m−3 Dm = N/A Mg m−3 Dm measured by not measured |
a = 7.885 (1) Å | Melting point: Not measured K |
b = 10.026 (1) Å | Mo Kα radiation, λ = 0.71069 Å |
c = 43.761 (3) Å | µ = 0.07 mm−1 |
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 tube | Rint = 0.018 |
Graphite monochromator | θmax = 24.4°, θmin = 2.2° |
0.5° φ scans and ω scans | h = −8→8 |
10828 measured reflections | k = −11→11 |
7844 independent reflections | l = −43→50 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.189 | H 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 reflections | Δρmax = 2.01 e Å−3 |
609 parameters | Δρmin = −1.04 e Å−3 |
3 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O2X | 0.0568 (7) | 0.9608 (5) | 0.38811 (13) | 0.0346 (15) | |
H2X | −0.015 (15) | 1.006 (13) | 0.377 (3) | 0.14 (6)* | |
O1X | 0.2552 (7) | 1.2477 (6) | 0.60021 (13) | 0.0399 (15) | |
H1X | 0.133 (6) | 1.212 (9) | 0.607 (2) | 0.06 (3)* | |
N1GC | −0.0762 (8) | 1.1054 (6) | 0.34703 (17) | 0.0386 (19) | |
C15X | 0.2188 (9) | 1.1806 (7) | 0.4176 (2) | 0.033 (2) | |
H15X | 0.1555 | 1.2298 | 0.4067 | 0.039* | |
C14X | 0.3478 (8) | 1.2529 (7) | 0.44143 (19) | 0.0280 (19) | |
H14X | 0.3682 | 1.3507 | 0.4470 | 0.034* | |
C3X | 0.7922 (9) | 1.4408 (8) | 0.45104 (19) | 0.032 (2) | |
H3X1 | 0.7159 | 1.3998 | 0.4320 | 0.039* | |
H3X2 | 0.8506 | 1.5434 | 0.4494 | 0.039* | |
C1X | 0.5819 (9) | 1.2646 (7) | 0.48415 (17) | 0.0242 (18) | |
C7X | 0.4899 (9) | 1.2577 (7) | 0.51427 (19) | 0.031 (2) | |
C10X | 0.3249 (10) | 1.2445 (7) | 0.5711 (2) | 0.033 (2) | |
C16X | 0.1855 (9) | 1.0373 (8) | 0.41012 (18) | 0.0276 (19) | |
C17X | 0.2801 (10) | 0.9684 (8) | 0.42534 (19) | 0.032 (2) | |
H17X | 0.2590 | 0.8705 | 0.4199 | 0.038* | |
C8X | 0.5864 (10) | 1.3236 (8) | 0.5420 (2) | 0.031 (2) | |
H8X | 0.7117 | 1.3720 | 0.5415 | 0.037* | |
C2GC | −0.1659 (10) | 1.3076 (8) | 0.3670 (2) | 0.039 (2) | |
C2X | 0.6735 (10) | 1.4215 (8) | 0.4785 (2) | 0.035 (2) | |
H2X1 | 0.5795 | 1.4652 | 0.4750 | 0.042* | |
H2X2 | 0.7477 | 1.4723 | 0.4971 | 0.042* | |
C6X | 0.7347 (9) | 1.2005 (8) | 0.4872 (2) | 0.034 (2) | |
H6X1 | 0.8134 | 1.2484 | 0.5056 | 0.040* | |
H6X2 | 0.6816 | 1.0990 | 0.4903 | 0.040* | |
C9X | 0.5081 (10) | 1.3213 (8) | 0.5698 (2) | 0.035 (2) | |
H9X | 0.5771 | 1.3711 | 0.5878 | 0.042* | |
C11X | 0.2234 (9) | 1.1772 (7) | 0.54547 (19) | 0.0290 (19) | |
H11X | 0.0995 | 1.1255 | 0.5466 | 0.035* | |
C1GC | −0.0382 (10) | 1.2572 (8) | 0.3542 (2) | 0.033 (2) | |
C18X | 0.4084 (9) | 1.0415 (7) | 0.44898 (18) | 0.0275 (18) | |
H18X | 0.4710 | 0.9916 | 0.4598 | 0.033* | |
C13X | 0.4449 (9) | 1.1845 (8) | 0.45684 (19) | 0.031 (2) | |
C12X | 0.3052 (9) | 1.1853 (8) | 0.5170 (2) | 0.034 (2) | |
H12X | 0.2329 | 1.1401 | 0.4990 | 0.041* | |
C4GC | 0.0429 (13) | 1.5486 (9) | 0.3664 (2) | 0.051 (3) | |
H4GC | 0.0699 | 1.6479 | 0.3708 | 0.061* | |
C3GC | −0.1199 (12) | 1.4562 (8) | 0.3729 (2) | 0.044 (2) | |
H3GC | −0.2056 | 1.4935 | 0.3818 | 0.052* | |
C6GC | 0.1281 (10) | 1.3479 (8) | 0.3471 (2) | 0.038 (2) | |
C5GC | 0.1667 (12) | 1.4944 (9) | 0.3534 (2) | 0.048 (2) | |
H5GC | 0.2799 | 1.5573 | 0.3485 | 0.058* | |
C4X | 0.9342 (10) | 1.3724 (8) | 0.4535 (2) | 0.042 (2) | |
H4X1 | 1.0225 | 1.4230 | 0.4706 | 0.051* | |
H4X2 | 0.9984 | 1.3788 | 0.4343 | 0.051* | |
C7GC | −0.3441 (12) | 1.2118 (9) | 0.3743 (2) | 0.055 (3) | |
H7C1 | −0.3991 | 1.1457 | 0.3563 | 0.083* | |
H7C2 | −0.4214 | 1.2680 | 0.3801 | 0.083* | |
H7C3 | −0.3297 | 1.1585 | 0.3915 | 0.083* | |
C8GC | 0.2693 (11) | 1.2911 (10) | 0.3330 (2) | 0.055 (3) | |
H8C1 | 0.3080 | 1.2363 | 0.3476 | 0.083* | |
H8C2 | 0.3729 | 1.3706 | 0.3281 | 0.083* | |
H8C3 | 0.2174 | 1.2299 | 0.3141 | 0.083* | |
C5X | 0.8481 (10) | 1.2142 (8) | 0.4595 (2) | 0.040 (2) | |
H5X1 | 0.7722 | 1.1610 | 0.4412 | 0.048* | |
H5X2 | 0.9440 | 1.1725 | 0.4630 | 0.048* | |
O2Y | 0.8929 (8) | 0.5824 (7) | 0.23675 (18) | 0.060 (2) | |
H2Y | 0.90 (2) | 0.526 (18) | 0.254 (3) | 0.21 (9)* | |
C15Y | 0.7387 (11) | 0.3789 (9) | 0.2014 (2) | 0.046 (2) | |
H15Y | 0.7966 | 0.3220 | 0.2108 | 0.055* | |
C17Y | 0.6866 (11) | 0.5972 (9) | 0.1971 (2) | 0.053 (3) | |
H17Y | 0.7084 | 0.6933 | 0.2045 | 0.064* | |
C14Y | 0.6115 (11) | 0.3213 (9) | 0.1757 (2) | 0.047 (2) | |
H14Y | 0.5830 | 0.2239 | 0.1688 | 0.057* | |
C18Y | 0.5727 (12) | 0.5402 (10) | 0.1727 (3) | 0.057 (3) | |
H18Y | 0.5187 | 0.5989 | 0.1630 | 0.069* | |
C16Y | 0.7741 (11) | 0.5172 (9) | 0.2119 (2) | 0.049 (3) | |
C1Y | 0.4139 (13) | 0.3416 (11) | 0.1307 (3) | 0.068 (3) | |
C13Y | 0.5296 (10) | 0.4002 (10) | 0.1608 (2) | 0.047 (3) | |
C2Y | 0.3142 (13) | 0.1793 (12) | 0.1292 (3) | 0.073 (4) | |
H2Y1 | 0.2511 | 0.1461 | 0.1088 | 0.087* | |
H2Y2 | 0.4037 | 0.1304 | 0.1316 | 0.087* | |
C6Y | 0.2556 (13) | 0.4057 (14) | 0.1284 (3) | 0.076 (4) | |
H6Y1 | 0.3078 | 0.5104 | 0.1299 | 0.091* | |
H6Y2 | 0.1913 | 0.3738 | 0.1080 | 0.091* | |
C8GD | 0.552 (2) | 0.8235 (17) | 0.0041 (4) | 0.120 (5)* | |
N1GA | 0.0375 (8) | 0.4119 (6) | 0.27087 (18) | 0.043 (2) | |
C1GA | −0.0058 (10) | 0.2632 (8) | 0.2645 (2) | 0.036 (2) | |
C2GA | −0.1769 (10) | 0.1761 (9) | 0.2720 (2) | 0.038 (2) | |
C6GA | 0.1093 (11) | 0.2044 (8) | 0.2501 (2) | 0.045 (2) | |
C4GA | −0.1034 (14) | −0.0284 (9) | 0.2531 (3) | 0.063 (3) | |
H4GA | −0.1366 | −0.1285 | 0.2492 | 0.075* | |
C3GA | −0.2193 (12) | 0.0321 (9) | 0.2666 (2) | 0.049 (3) | |
H3GA | −0.3320 | −0.0275 | 0.2724 | 0.059* | |
C7GA | −0.3097 (11) | 0.2448 (11) | 0.2860 (3) | 0.062 (3) | |
H7A1 | −0.4204 | 0.1704 | 0.2903 | 0.094* | |
H7A2 | −0.3377 | 0.3050 | 0.2715 | 0.094* | |
H7A3 | −0.2553 | 0.3024 | 0.3051 | 0.094* | |
C5GA | 0.0624 (12) | 0.0581 (9) | 0.2450 (2) | 0.054 (3) | |
H5GA | 0.1444 | 0.0170 | 0.2361 | 0.065* | |
C8GA | 0.2956 (11) | 0.2983 (10) | 0.2414 (3) | 0.062 (3) | |
H8A1 | 0.3641 | 0.2381 | 0.2336 | 0.092* | |
H8A2 | 0.3602 | 0.3590 | 0.2596 | 0.092* | |
H8A3 | 0.2810 | 0.3576 | 0.2255 | 0.092* | |
N1GB | 0.5326 (8) | 0.8483 (7) | 0.34991 (18) | 0.044 (2) | |
C2GB | 0.5781 (10) | 0.7107 (8) | 0.3035 (2) | 0.043 (3) | |
C1GB | 0.4843 (10) | 0.7902 (7) | 0.3193 (2) | 0.035 (2) | |
C5GB | 0.3022 (10) | 0.7659 (8) | 0.2720 (2) | 0.042 (2) | |
H5GB | 0.2079 | 0.7842 | 0.2610 | 0.050* | |
C6GB | 0.3441 (9) | 0.8180 (8) | 0.3033 (2) | 0.036 (2) | |
C3GB | 0.5341 (11) | 0.6617 (8) | 0.2731 (2) | 0.042 (2) | |
H3GB | 0.5992 | 0.6084 | 0.2628 | 0.051* | |
C4GB | 0.3988 (12) | 0.6883 (9) | 0.2573 (2) | 0.051 (3) | |
H4GB | 0.3707 | 0.6537 | 0.2363 | 0.062* | |
C7GB | 0.7345 (12) | 0.6824 (10) | 0.3203 (3) | 0.059 (3) | |
H7B1 | 0.7917 | 0.6328 | 0.3058 | 0.088* | |
H7B2 | 0.6890 | 0.6237 | 0.3370 | 0.088* | |
H7B3 | 0.8228 | 0.7727 | 0.3287 | 0.088* | |
C8GB | 0.2410 (11) | 0.9039 (10) | 0.3188 (2) | 0.054 (3) | |
H8B1 | 0.1406 | 0.9031 | 0.3050 | 0.081* | |
H8B2 | 0.3206 | 1.0017 | 0.3238 | 0.081* | |
H8B3 | 0.1944 | 0.8629 | 0.3377 | 0.081* | |
C3Y | 0.1760 (12) | 0.1376 (11) | 0.1543 (3) | 0.071 (4) | |
H3Y1 | 0.1151 | 0.0337 | 0.1517 | 0.086* | |
H3Y2 | 0.2404 | 0.1624 | 0.1748 | 0.086* | |
C5Y | 0.1199 (12) | 0.3643 (12) | 0.1532 (3) | 0.071 (3) | |
H5Y1 | 0.1824 | 0.4014 | 0.1736 | 0.085* | |
H5Y2 | 0.0270 | 0.4095 | 0.1503 | 0.085* | |
C4Y | 0.0331 (13) | 0.2126 (14) | 0.1528 (3) | 0.084 (4) | |
H4Y1 | −0.0448 | 0.1765 | 0.1338 | 0.101* | |
H4Y2 | −0.0434 | 0.1916 | 0.1705 | 0.101* | |
N1GD | 0.7625 (18) | 0.6773 (16) | −0.0089 (4) | 0.145 (5)* | |
C1GD | 0.8242 (16) | 0.8047 (10) | 0.0109 (3) | 0.142 (6)* | |
C2GD | 0.9972 (14) | 0.8508 (13) | 0.0245 (3) | 0.175 (8)* | |
C3GD | 1.0520 (11) | 0.9696 (14) | 0.0458 (3) | 0.121 (5)* | |
C4GD | 0.9337 (16) | 1.0423 (11) | 0.0534 (3) | 0.152 (7)* | |
C5GD | 0.7607 (14) | 0.9962 (11) | 0.0398 (3) | 0.123 (5)* | |
C6GD | 0.7059 (11) | 0.8774 (11) | 0.0185 (2) | 0.085 (4)* | |
C1GE | 0.2611 (17) | 0.8023 (14) | 0.1545 (4) | 0.114 (5)* | |
C2GE | 0.443 (2) | 0.8655 (17) | 0.1628 (3) | 0.35 (2)* | |
C3GE | 0.5684 (13) | 0.8879 (16) | 0.1404 (5) | 0.144 (6)* | |
C4GE | 0.512 (2) | 0.8469 (19) | 0.1097 (4) | 0.303 (17)* | |
C5GE | 0.330 (3) | 0.784 (2) | 0.1014 (3) | 0.194 (9)* | |
C6GE | 0.2047 (16) | 0.7613 (15) | 0.1238 (4) | 0.187 (9)* | |
C7Y | 0.5469 (8) | 0.3753 (6) | 0.10601 (16) | 0.079 (3)* | |
C8Y | 0.5746 (7) | 0.4946 (7) | 0.09018 (14) | 0.186 (9)* | |
C9Y | 0.7059 (9) | 0.5267 (7) | 0.06884 (14) | 0.228 (12)* | |
C10Y | 0.8096 (8) | 0.4396 (7) | 0.06333 (15) | 0.191 (9)* | |
C11Y | 0.7819 (9) | 0.3202 (7) | 0.07917 (17) | 0.141 (6)* | |
C12Y | 0.6505 (11) | 0.2881 (6) | 0.10051 (19) | 0.105 (4)* | |
C8GE | 0.0258 (13) | 0.7083 (14) | 0.1269 (3) | 0.218 (11)* | |
C7GD | 1.1050 (18) | 0.7510 (12) | 0.0146 (3) | 0.202 (10)* | |
O1Y | 0.9406 (10) | 0.4720 (9) | 0.04199 (17) | 0.194 (6)* | |
N1GE | 0.1610 (14) | 0.7895 (12) | 0.1828 (3) | 0.182 (7)* | |
C7GE | 0.5029 (15) | 0.9148 (11) | 0.1908 (3) | 0.186 (9)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2X | 0.037 (3) | 0.028 (3) | 0.035 (4) | 0.008 (2) | −0.006 (3) | −0.004 (2) |
O1X | 0.050 (4) | 0.046 (3) | 0.020 (4) | 0.011 (3) | 0.008 (3) | 0.003 (2) |
N1GC | 0.036 (4) | 0.035 (4) | 0.044 (5) | 0.012 (3) | −0.009 (3) | 0.006 (3) |
C15X | 0.026 (4) | 0.025 (4) | 0.049 (6) | 0.011 (3) | −0.001 (4) | 0.007 (4) |
C14X | 0.023 (4) | 0.025 (4) | 0.039 (6) | 0.013 (3) | 0.003 (4) | 0.002 (3) |
C3X | 0.032 (4) | 0.037 (4) | 0.026 (6) | 0.008 (3) | 0.005 (4) | 0.007 (3) |
C1X | 0.029 (4) | 0.024 (4) | 0.015 (5) | 0.004 (3) | 0.000 (3) | −0.002 (3) |
C7X | 0.032 (4) | 0.022 (4) | 0.041 (6) | 0.010 (3) | −0.001 (4) | 0.011 (3) |
C10X | 0.046 (5) | 0.025 (4) | 0.029 (6) | 0.013 (4) | −0.001 (4) | 0.008 (3) |
C16X | 0.021 (4) | 0.038 (4) | 0.020 (5) | 0.004 (3) | 0.002 (3) | 0.000 (3) |
C17X | 0.039 (4) | 0.025 (4) | 0.031 (6) | 0.008 (3) | 0.001 (4) | 0.007 (3) |
C8X | 0.028 (4) | 0.033 (4) | 0.031 (6) | 0.008 (3) | 0.000 (4) | 0.005 (3) |
C2GC | 0.041 (5) | 0.037 (5) | 0.035 (6) | 0.008 (4) | −0.006 (4) | 0.002 (4) |
C2X | 0.041 (4) | 0.030 (4) | 0.032 (6) | 0.010 (4) | −0.010 (4) | 0.003 (3) |
C6X | 0.032 (4) | 0.033 (4) | 0.036 (6) | 0.011 (3) | −0.007 (4) | 0.003 (3) |
C9X | 0.038 (4) | 0.028 (4) | 0.037 (6) | 0.008 (3) | −0.007 (4) | 0.002 (3) |
C11X | 0.029 (4) | 0.031 (4) | 0.028 (6) | 0.010 (3) | 0.007 (4) | 0.000 (3) |
C1GC | 0.042 (5) | 0.029 (4) | 0.030 (6) | 0.012 (4) | −0.009 (4) | 0.010 (3) |
C18X | 0.031 (4) | 0.034 (4) | 0.015 (5) | 0.009 (3) | −0.006 (3) | −0.001 (3) |
C13X | 0.026 (4) | 0.032 (4) | 0.032 (6) | 0.003 (3) | 0.003 (4) | 0.012 (3) |
C12X | 0.031 (4) | 0.031 (4) | 0.038 (6) | 0.007 (3) | −0.007 (4) | 0.003 (3) |
C4GC | 0.065 (6) | 0.038 (5) | 0.048 (7) | 0.014 (5) | −0.008 (5) | 0.005 (4) |
C3GC | 0.064 (6) | 0.035 (5) | 0.035 (6) | 0.023 (4) | 0.001 (4) | 0.000 (4) |
C6GC | 0.038 (4) | 0.032 (5) | 0.040 (6) | 0.007 (4) | −0.009 (4) | 0.004 (4) |
C5GC | 0.049 (5) | 0.046 (5) | 0.041 (7) | 0.003 (4) | −0.001 (5) | 0.015 (4) |
C4X | 0.032 (4) | 0.041 (5) | 0.047 (7) | 0.003 (4) | 0.009 (4) | 0.004 (4) |
C7GC | 0.069 (6) | 0.048 (6) | 0.040 (7) | 0.011 (5) | 0.001 (5) | −0.003 (4) |
C8GC | 0.049 (5) | 0.063 (6) | 0.056 (8) | 0.020 (5) | 0.005 (5) | 0.012 (5) |
C5X | 0.040 (4) | 0.043 (5) | 0.042 (7) | 0.019 (4) | 0.015 (4) | 0.007 (4) |
O2Y | 0.055 (4) | 0.057 (4) | 0.059 (6) | 0.014 (3) | −0.028 (4) | −0.020 (4) |
C15Y | 0.046 (5) | 0.051 (6) | 0.036 (7) | 0.014 (4) | −0.016 (4) | −0.007 (4) |
C17Y | 0.049 (5) | 0.044 (5) | 0.067 (8) | 0.023 (4) | −0.022 (5) | −0.016 (5) |
C14Y | 0.042 (5) | 0.050 (5) | 0.046 (7) | 0.013 (4) | 0.007 (5) | −0.008 (4) |
C18Y | 0.055 (6) | 0.069 (7) | 0.061 (8) | 0.043 (5) | −0.001 (5) | −0.007 (5) |
C16Y | 0.042 (5) | 0.043 (5) | 0.061 (8) | 0.014 (4) | 0.000 (5) | 0.002 (4) |
C1Y | 0.059 (6) | 0.080 (8) | 0.060 (9) | 0.022 (6) | −0.023 (6) | −0.015 (6) |
C13Y | 0.031 (4) | 0.055 (6) | 0.048 (7) | 0.010 (4) | 0.004 (4) | −0.015 (4) |
C2Y | 0.057 (6) | 0.085 (8) | 0.070 (10) | 0.026 (6) | −0.024 (6) | −0.034 (6) |
C6Y | 0.050 (6) | 0.128 (10) | 0.042 (9) | 0.025 (6) | −0.021 (6) | −0.015 (6) |
N1GA | 0.041 (4) | 0.025 (4) | 0.062 (6) | 0.008 (3) | −0.015 (4) | 0.006 (3) |
C1GA | 0.036 (4) | 0.037 (5) | 0.032 (6) | 0.010 (4) | −0.004 (4) | 0.005 (4) |
C2GA | 0.032 (4) | 0.054 (5) | 0.022 (6) | 0.004 (4) | −0.005 (4) | 0.006 (4) |
C6GA | 0.037 (5) | 0.033 (5) | 0.057 (7) | 0.003 (4) | 0.001 (4) | 0.001 (4) |
C4GA | 0.071 (7) | 0.027 (5) | 0.082 (9) | 0.006 (5) | −0.010 (6) | 0.007 (5) |
C3GA | 0.050 (5) | 0.036 (5) | 0.045 (7) | −0.009 (4) | −0.006 (5) | 0.012 (4) |
C7GA | 0.034 (5) | 0.091 (8) | 0.059 (8) | 0.009 (5) | 0.021 (5) | 0.027 (6) |
C5GA | 0.057 (6) | 0.039 (5) | 0.060 (8) | 0.011 (5) | −0.001 (5) | −0.005 (4) |
C8GA | 0.041 (5) | 0.050 (6) | 0.083 (9) | 0.000 (4) | 0.019 (5) | 0.003 (5) |
N1GB | 0.035 (4) | 0.036 (4) | 0.049 (6) | −0.004 (3) | −0.012 (4) | 0.003 (3) |
C2GB | 0.030 (4) | 0.029 (4) | 0.067 (8) | 0.004 (4) | 0.001 (4) | 0.022 (4) |
C1GB | 0.034 (4) | 0.022 (4) | 0.039 (6) | −0.003 (3) | 0.009 (4) | 0.005 (3) |
C5GB | 0.039 (5) | 0.033 (5) | 0.049 (7) | 0.004 (4) | −0.006 (4) | 0.013 (4) |
C6GB | 0.027 (4) | 0.032 (4) | 0.051 (7) | 0.008 (3) | 0.008 (4) | 0.014 (4) |
C3GB | 0.052 (5) | 0.031 (4) | 0.040 (7) | 0.007 (4) | 0.012 (5) | 0.008 (4) |
C4GB | 0.055 (5) | 0.033 (5) | 0.054 (7) | −0.001 (4) | −0.007 (5) | 0.011 (4) |
C7GB | 0.056 (6) | 0.047 (5) | 0.074 (9) | 0.017 (4) | −0.001 (5) | 0.013 (5) |
C8GB | 0.045 (5) | 0.054 (6) | 0.058 (8) | 0.009 (4) | 0.003 (5) | 0.014 (5) |
C3Y | 0.042 (5) | 0.069 (7) | 0.093 (11) | 0.013 (5) | 0.000 (6) | −0.026 (6) |
C5Y | 0.045 (6) | 0.095 (9) | 0.068 (10) | 0.025 (6) | −0.022 (6) | −0.018 (6) |
C4Y | 0.046 (6) | 0.108 (10) | 0.084 (11) | 0.014 (6) | 0.003 (6) | −0.025 (7) |
Geometric parameters (Å, º) top
O2X—C16X | 1.366 (9) | N1GA—C1GA | 1.418 (10) |
O1X—C10X | 1.403 (10) | C1GA—C6GA | 1.374 (12) |
N1GC—C1GC | 1.458 (10) | C1GA—C2GA | 1.412 (11) |
C15X—C16X | 1.383 (10) | C2GA—C3GA | 1.370 (12) |
C15X—C14X | 1.411 (11) | C2GA—C7GA | 1.543 (13) |
C14X—C13X | 1.379 (10) | C6GA—C5GA | 1.389 (12) |
C3X—C4X | 1.497 (11) | C6GA—C8GA | 1.541 (11) |
C3X—C2X | 1.528 (11) | C4GA—C3GA | 1.374 (14) |
C1X—C7X | 1.517 (11) | C4GA—C5GA | 1.386 (13) |
C1X—C2X | 1.546 (10) | N1GB—C1GB | 1.408 (11) |
C1X—C6X | 1.546 (10) | C2GB—C3GB | 1.375 (12) |
C1X—C13X | 1.565 (10) | C2GB—C1GB | 1.408 (12) |
C7X—C8X | 1.406 (11) | C2GB—C7GB | 1.535 (12) |
C7X—C12X | 1.413 (10) | C1GB—C6GB | 1.407 (11) |
C10X—C11X | 1.353 (11) | C5GB—C4GB | 1.389 (13) |
C10X—C9X | 1.403 (10) | C5GB—C6GB | 1.416 (13) |
C16X—C17X | 1.364 (10) | C6GB—C8GB | 1.501 (13) |
C17X—C18X | 1.403 (10) | C3GB—C4GB | 1.363 (12) |
C8X—C9X | 1.377 (11) | C3Y—C4Y | 1.548 (15) |
C2GC—C1GC | 1.378 (11) | C5Y—C4Y | 1.449 (16) |
C2GC—C3GC | 1.413 (11) | N1GD—C1GD | 1.419 (17) |
C2GC—C7GC | 1.481 (12) | C1GD—C2GD | 1.3900 |
C6X—C5X | 1.514 (11) | C1GD—C6GD | 1.3900 |
C11X—C12X | 1.414 (11) | C2GD—C3GD | 1.3900 |
C1GC—C6GC | 1.390 (11) | C2GD—C7GD | 1.554 (14) |
C18X—C13X | 1.380 (10) | C3GD—C4GD | 1.3900 |
C4GC—C3GC | 1.369 (12) | C4GD—C5GD | 1.3900 |
C4GC—C5GC | 1.378 (13) | C5GD—C6GD | 1.3900 |
C6GC—C5GC | 1.402 (12) | C1GE—C2GE | 1.3900 |
C6GC—C8GC | 1.530 (12) | C1GE—C6GE | 1.3900 |
C4X—C5X | 1.555 (11) | C1GE—N1GE | 1.478 (14) |
O2Y—C16Y | 1.383 (11) | C2GE—C7GE | 1.297 (15) |
C15Y—C16Y | 1.360 (12) | C2GE—C3GE | 1.3900 |
C15Y—C14Y | 1.434 (12) | C3GE—C4GE | 1.3900 |
C17Y—C18Y | 1.339 (13) | C4GE—C5GE | 1.3900 |
C17Y—C16Y | 1.400 (12) | C5GE—C6GE | 1.3900 |
C14Y—C13Y | 1.365 (13) | C6GE—C8GE | 1.351 (15) |
C18Y—C13Y | 1.385 (12) | C7Y—C8Y | 1.3900 |
C1Y—C7Y | 1.506 (13) | C7Y—C12Y | 1.3900 |
C1Y—C13Y | 1.542 (13) | C8Y—C9Y | 1.3900 |
C1Y—C2Y | 1.554 (15) | C9Y—C10Y | 1.3900 |
C1Y—C6Y | 1.583 (15) | C10Y—O1Y | 1.3885 |
C2Y—C3Y | 1.550 (16) | C10Y—C11Y | 1.3900 |
C6Y—C5Y | 1.529 (16) | C11Y—C12Y | 1.3900 |
C8GD—C6GD | 1.280 (17) | | |
| | | |
C16X—C15X—C14X | 119.2 (7) | C6GA—C1GA—C2GA | 120.3 (7) |
C13X—C14X—C15X | 121.3 (7) | C6GA—C1GA—N1GA | 121.9 (7) |
C4X—C3X—C2X | 112.8 (7) | C2GA—C1GA—N1GA | 117.7 (7) |
C7X—C1X—C2X | 109.3 (6) | C3GA—C2GA—C1GA | 118.4 (8) |
C7X—C1X—C6X | 108.6 (6) | C3GA—C2GA—C7GA | 122.0 (7) |
C2X—C1X—C6X | 106.2 (6) | C1GA—C2GA—C7GA | 119.6 (7) |
C7X—C1X—C13X | 111.1 (6) | C1GA—C6GA—C5GA | 119.7 (8) |
C2X—C1X—C13X | 110.6 (6) | C1GA—C6GA—C8GA | 120.9 (7) |
C6X—C1X—C13X | 111.0 (6) | C5GA—C6GA—C8GA | 119.3 (8) |
C8X—C7X—C12X | 115.0 (8) | C3GA—C4GA—C5GA | 119.3 (8) |
C8X—C7X—C1X | 121.2 (6) | C2GA—C3GA—C4GA | 121.9 (8) |
C12X—C7X—C1X | 123.8 (7) | C4GA—C5GA—C6GA | 120.3 (9) |
C11X—C10X—C9X | 121.2 (8) | C3GB—C2GB—C1GB | 120.7 (8) |
C11X—C10X—O1X | 123.2 (7) | C3GB—C2GB—C7GB | 119.9 (9) |
C9X—C10X—O1X | 115.6 (7) | C1GB—C2GB—C7GB | 119.3 (9) |
C17X—C16X—O2X | 118.4 (7) | N1GB—C1GB—C6GB | 119.4 (7) |
C17X—C16X—C15X | 119.9 (7) | N1GB—C1GB—C2GB | 122.0 (8) |
O2X—C16X—C15X | 121.7 (7) | C6GB—C1GB—C2GB | 118.5 (8) |
C16X—C17X—C18X | 120.4 (7) | C4GB—C5GB—C6GB | 120.2 (8) |
C9X—C8X—C7X | 123.2 (7) | C1GB—C6GB—C5GB | 119.3 (8) |
C1GC—C2GC—C3GC | 117.0 (7) | C1GB—C6GB—C8GB | 120.9 (8) |
C1GC—C2GC—C7GC | 122.1 (7) | C5GB—C6GB—C8GB | 119.8 (8) |
C3GC—C2GC—C7GC | 120.9 (8) | C4GB—C3GB—C2GB | 121.3 (9) |
C3X—C2X—C1X | 113.5 (6) | C3GB—C4GB—C5GB | 120.0 (9) |
C5X—C6X—C1X | 113.5 (6) | C4Y—C3Y—C2Y | 112.5 (11) |
C8X—C9X—C10X | 119.1 (7) | C4Y—C5Y—C6Y | 113.2 (10) |
C10X—C11X—C12X | 118.8 (7) | C5Y—C4Y—C3Y | 110.1 (8) |
C2GC—C1GC—C6GC | 121.8 (7) | C2GD—C1GD—C6GD | 120.0 |
C2GC—C1GC—N1GC | 120.4 (7) | C2GD—C1GD—N1GD | 120.3 (10) |
C6GC—C1GC—N1GC | 117.8 (7) | C6GD—C1GD—N1GD | 119.5 (10) |
C13X—C18X—C17X | 121.0 (7) | C3GD—C2GD—C1GD | 120.0 |
C14X—C13X—C18X | 118.1 (7) | C3GD—C2GD—C7GD | 127.5 (11) |
C14X—C13X—C1X | 120.7 (7) | C1GD—C2GD—C7GD | 112.4 (11) |
C18X—C13X—C1X | 121.0 (6) | C2GD—C3GD—C4GD | 120.0 |
C7X—C12X—C11X | 122.7 (7) | C5GD—C4GD—C3GD | 120.0 |
C3GC—C4GC—C5GC | 118.6 (8) | C6GD—C5GD—C4GD | 120.0 |
C4GC—C3GC—C2GC | 122.8 (8) | C8GD—C6GD—C5GD | 126.9 (11) |
C1GC—C6GC—C5GC | 118.9 (8) | C8GD—C6GD—C1GD | 113.1 (11) |
C1GC—C6GC—C8GC | 121.5 (7) | C5GD—C6GD—C1GD | 120.0 |
C5GC—C6GC—C8GC | 119.6 (7) | C2GE—C1GE—C6GE | 120.0 |
C4GC—C5GC—C6GC | 120.9 (8) | C2GE—C1GE—N1GE | 108.1 (13) |
C3X—C4X—C5X | 110.3 (6) | C6GE—C1GE—N1GE | 131.8 (13) |
C6X—C5X—C4X | 110.7 (7) | C7GE—C2GE—C1GE | 122.8 (14) |
C16Y—C15Y—C14Y | 118.3 (8) | C7GE—C2GE—C3GE | 117.0 (14) |
C18Y—C17Y—C16Y | 121.0 (8) | C1GE—C2GE—C3GE | 120.0 |
C13Y—C14Y—C15Y | 123.0 (8) | C2GE—C3GE—C4GE | 120.0 |
C17Y—C18Y—C13Y | 123.4 (9) | C5GE—C4GE—C3GE | 120.0 |
C15Y—C16Y—O2Y | 122.8 (8) | C6GE—C5GE—C4GE | 120.0 |
C15Y—C16Y—C17Y | 118.7 (9) | C8GE—C6GE—C5GE | 141.1 (14) |
O2Y—C16Y—C17Y | 118.5 (8) | C8GE—C6GE—C1GE | 98.9 (14) |
C7Y—C1Y—C13Y | 104.0 (7) | C5GE—C6GE—C1GE | 120.0 |
C7Y—C1Y—C2Y | 110.7 (8) | C8Y—C7Y—C12Y | 120.0 |
C13Y—C1Y—C2Y | 112.4 (9) | C8Y—C7Y—C1Y | 121.6 (5) |
C7Y—C1Y—C6Y | 115.9 (9) | C12Y—C7Y—C1Y | 118.3 (5) |
C13Y—C1Y—C6Y | 110.6 (9) | C9Y—C8Y—C7Y | 120.0 |
C2Y—C1Y—C6Y | 103.4 (8) | C8Y—C9Y—C10Y | 120.0 |
C14Y—C13Y—C18Y | 115.5 (9) | O1Y—C10Y—C9Y | 119.8 |
C14Y—C13Y—C1Y | 121.9 (8) | O1Y—C10Y—C11Y | 120.2 |
C18Y—C13Y—C1Y | 122.2 (9) | C9Y—C10Y—C11Y | 120.0 |
C3Y—C2Y—C1Y | 113.2 (8) | C12Y—C11Y—C10Y | 120.0 |
C5Y—C6Y—C1Y | 114.1 (10) | C11Y—C12Y—C7Y | 120.0 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2X—H2X···N1GC | 0.98 (3) | 1.85 (6) | 2.783 (8) | 159 (12) |
O1X—H1X···O2Xi | 0.97 (3) | 1.92 (6) | 2.752 (7) | 142 (7) |
O2Y—H2Y···N1GAii | 0.97 (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 = 631.87 | Dx = 1.138 Mg m−3 Dm = N/A Mg m−3 Dm measured by not measured |
Monoclinic, P21/n | Melting point: 361.15K for guest release onset temp. and 463.15K fro host melting K |
a = 9.807 (1) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 25.464 (2) Å | µ = 0.07 mm−1 |
c = 29.842 (3) Å | T = 173 K |
β = 98.28 (1)° | Prism, colourless |
V = 7374.6 (12) Å3 | 0.80 × 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 tube | Rint = 0.070 |
Graphite monochromator | θmax = 25.7°, θmin = 2.1° |
0.8° φ scans and ω scans | h = 0→11 |
13682 measured reflections | k = 0→30 |
13682 independent reflections | l = −36→35 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.086 | H 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 reflections | Δρmax = 0.63 e Å−3 |
923 parameters | Δρmin = −0.25 e Å−3 |
24 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1X | 0.0281 (2) | 0.56325 (9) | 0.02685 (9) | 0.0475 (6) | |
O1Y | −0.2937 (3) | 1.41895 (10) | 0.22382 (10) | 0.0560 (7) | |
H1Y | −0.209 (3) | 1.4315 (15) | 0.2389 (13) | 0.076 (14)* | |
O2X | 0.0233 (3) | 0.91931 (10) | 0.00057 (10) | 0.0556 (7) | |
H2X | −0.056 (4) | 0.9389 (18) | −0.0028 (18) | 0.12 (2)* | |
C8X | 0.1682 (3) | 0.67842 (13) | 0.08885 (12) | 0.0411 (8) | |
H8X | 0.2561 | 0.6943 | 0.0966 | 0.049* | |
C7X | 0.0543 (3) | 0.70114 (12) | 0.10456 (10) | 0.0310 (7) | |
C1Y | −0.3274 (3) | 1.23842 (14) | 0.10794 (11) | 0.0378 (8) | |
O2Y | −0.2805 (3) | 1.04680 (10) | 0.20892 (10) | 0.0614 (8) | |
H2Y | −0.187 (3) | 1.0354 (17) | 0.2147 (15) | 0.092 (16)* | |
C9X | 0.1573 (3) | 0.63385 (13) | 0.06251 (12) | 0.0438 (9) | |
H9X | 0.2370 | 0.6200 | 0.0520 | 0.053* | |
C11Y | −0.1820 (3) | 1.35598 (14) | 0.18136 (11) | 0.0407 (8) | |
H11Y | −0.0956 | 1.3728 | 0.1896 | 0.049* | |
C12X | −0.0711 (3) | 0.67566 (12) | 0.09183 (11) | 0.0356 (8) | |
H12X | −0.1517 | 0.6899 | 0.1014 | 0.043* | |
C12Y | −0.1925 (3) | 1.31247 (14) | 0.15321 (11) | 0.0396 (8) | |
H12Y | −0.1117 | 1.2998 | 0.1427 | 0.048* | |
C14X | −0.0749 (3) | 0.82181 (13) | 0.08135 (11) | 0.0374 (8) | |
H14X | −0.1544 | 0.8107 | 0.0936 | 0.045* | |
C7Y | −0.3167 (3) | 1.28669 (13) | 0.13978 (12) | 0.0388 (8) | |
C1X | 0.0645 (3) | 0.75286 (12) | 0.13139 (11) | 0.0331 (7) | |
C1GD | −0.1478 (3) | 0.74035 (16) | −0.07207 (13) | 0.0477 (9) | |
C10Y | −0.2977 (4) | 1.37471 (14) | 0.19727 (12) | 0.0445 (9) | |
C1GB | 0.5921 (3) | 0.74171 (16) | 0.19360 (12) | 0.0450 (9) | |
C13X | 0.0501 (3) | 0.79709 (12) | 0.09606 (11) | 0.0346 (8) | |
C2X | −0.0492 (3) | 0.75683 (13) | 0.16236 (11) | 0.0373 (8) | |
H2X1 | −0.0473 | 0.7925 | 0.1756 | 0.045* | |
H2X2 | −0.1402 | 0.7519 | 0.1437 | 0.045* | |
C16Y | −0.2858 (3) | 1.09364 (14) | 0.18613 (12) | 0.0442 (9) | |
N1GE | −0.2148 (3) | 0.98307 (13) | −0.01891 (13) | 0.0549 (9) | |
C18Y | −0.1919 (3) | 1.15828 (16) | 0.14128 (13) | 0.0539 (10) | |
H18Y | −0.1164 | 1.1700 | 0.1272 | 0.065* | |
C2Y | −0.2170 (3) | 1.24064 (15) | 0.07528 (12) | 0.0438 (9) | |
H2Y1 | −0.1251 | 1.2446 | 0.0937 | 0.053* | |
H2Y2 | −0.2176 | 1.2066 | 0.0592 | 0.053* | |
C15Y | −0.4024 (4) | 1.12448 (15) | 0.18429 (14) | 0.0530 (10) | |
H15Y | −0.4754 | 1.1137 | 0.2000 | 0.064* | |
C16X | 0.0259 (4) | 0.87859 (13) | 0.03076 (13) | 0.0442 (9) | |
C11X | −0.0829 (3) | 0.63017 (12) | 0.06564 (11) | 0.0362 (8) | |
H11X | −0.1701 | 0.6138 | 0.0578 | 0.043* | |
C18X | 0.1611 (4) | 0.81338 (15) | 0.07485 (13) | 0.0495 (9) | |
H18X | 0.2477 | 0.7966 | 0.0826 | 0.059* | |
C10X | 0.0323 (3) | 0.60907 (12) | 0.05116 (11) | 0.0347 (7) | |
C6X | 0.2044 (3) | 0.75738 (14) | 0.16318 (12) | 0.0434 (9) | |
H6X1 | 0.2803 | 0.7527 | 0.1450 | 0.052* | |
H6X2 | 0.2126 | 0.7931 | 0.1764 | 0.052* | |
C13Y | −0.3103 (3) | 1.18901 (13) | 0.13689 (11) | 0.0373 (8) | |
C15X | −0.0885 (3) | 0.86209 (13) | 0.04951 (12) | 0.0432 (9) | |
H15X | −0.1756 | 0.8782 | 0.0406 | 0.052* | |
C8Y | −0.4301 (4) | 1.30601 (15) | 0.15742 (15) | 0.0562 (11) | |
H8Y | −0.5167 | 1.2892 | 0.1496 | 0.067* | |
C6GB | 0.5836 (4) | 0.78593 (16) | 0.16577 (14) | 0.0522 (10) | |
C6Y | −0.4686 (3) | 1.23552 (16) | 0.07623 (13) | 0.0506 (10) | |
H6Y1 | −0.4751 | 1.2014 | 0.0602 | 0.061* | |
H6Y2 | −0.5439 | 1.2370 | 0.0950 | 0.061* | |
C5Y | −0.4889 (4) | 1.27890 (17) | 0.04179 (14) | 0.0581 (11) | |
H5Y1 | −0.4896 | 1.3131 | 0.0576 | 0.070* | |
H5Y2 | −0.5793 | 1.2745 | 0.0226 | 0.070* | |
C5GD | −0.1703 (4) | 0.7774 (2) | −0.14687 (15) | 0.0619 (12) | |
H5GD | −0.1749 | 0.8072 | −0.1662 | 0.074* | |
C5X | 0.2208 (3) | 0.71745 (16) | 0.20135 (12) | 0.0487 (9) | |
H5X1 | 0.3106 | 0.7230 | 0.2206 | 0.058* | |
H5X2 | 0.2211 | 0.6817 | 0.1884 | 0.058* | |
C5GB | 0.5717 (4) | 0.77942 (19) | 0.12005 (15) | 0.0585 (11) | |
H5GB | 0.5656 | 0.8095 | 0.1010 | 0.070* | |
C6GD | −0.1541 (3) | 0.78486 (16) | −0.10023 (15) | 0.0529 (10) | |
C3GD | −0.1746 (3) | 0.68518 (17) | −0.13774 (13) | 0.0541 (10) | |
H3GD | −0.1817 | 0.6510 | −0.1506 | 0.065* | |
C9Y | −0.4213 (4) | 1.34871 (16) | 0.18591 (15) | 0.0603 (11) | |
H9Y | −0.5007 | 1.3604 | 0.1978 | 0.072* | |
C4GD | −0.1799 (4) | 0.72778 (19) | −0.16581 (14) | 0.0587 (11) | |
H4GD | −0.1900 | 0.7234 | −0.1977 | 0.070* | |
C3X | −0.0334 (3) | 0.71665 (15) | 0.20069 (11) | 0.0434 (9) | |
H3X1 | −0.1077 | 0.7219 | 0.2195 | 0.052* | |
H3X2 | −0.0431 | 0.6808 | 0.1877 | 0.052* | |
C4Y | −0.3757 (4) | 1.27909 (18) | 0.01202 (13) | 0.0594 (11) | |
H4Y1 | −0.3889 | 1.3092 | −0.0092 | 0.071* | |
H4Y2 | −0.3803 | 1.2464 | −0.0061 | 0.071* | |
N1GD | −0.1342 (4) | 0.74661 (18) | −0.02525 (13) | 0.0626 (10) | |
C14Y | −0.4144 (3) | 1.17079 (15) | 0.16000 (13) | 0.0479 (9) | |
H14Y | −0.4964 | 1.1909 | 0.1590 | 0.058* | |
C3Y | −0.2354 (4) | 1.28322 (16) | 0.04122 (13) | 0.0544 (10) | |
H3Y1 | −0.1619 | 1.2810 | 0.0218 | 0.065* | |
H3Y2 | −0.2273 | 1.3177 | 0.0568 | 0.065* | |
C2GD | −0.1593 (3) | 0.69031 (15) | −0.09099 (12) | 0.0458 (9) | |
C17Y | −0.1787 (4) | 1.11145 (16) | 0.16512 (14) | 0.0560 (11) | |
H17Y | −0.0959 | 1.0917 | 0.1670 | 0.067* | |
C4GB | 0.5685 (4) | 0.7304 (2) | 0.10111 (14) | 0.0621 (12) | |
H4GB | 0.5613 | 0.7265 | 0.0692 | 0.075* | |
C17X | 0.1491 (4) | 0.85272 (15) | 0.04323 (14) | 0.0527 (10) | |
H17X | 0.2273 | 0.8624 | 0.0296 | 0.063* | |
N1GB | 0.6017 (4) | 0.7471 (2) | 0.24048 (14) | 0.0783 (13) | |
C4X | 0.1058 (4) | 0.72158 (17) | 0.23033 (12) | 0.0537 (10) | |
H4X1 | 0.1116 | 0.7558 | 0.2462 | 0.064* | |
H4X2 | 0.1160 | 0.6934 | 0.2534 | 0.064* | |
C3GB | 0.5757 (4) | 0.68665 (19) | 0.12869 (17) | 0.0631 (12) | |
H3GB | 0.5729 | 0.6526 | 0.1155 | 0.076* | |
C2GE | −0.4271 (4) | 0.93247 (15) | −0.01796 (14) | 0.0514 (10) | |
C7GD | −0.1558 (4) | 0.64279 (17) | −0.06120 (15) | 0.0660 (12) | |
H7D1 | −0.0664 | 0.6408 | −0.0418 | 0.099* | |
H7D2 | −0.1695 | 0.6112 | −0.0800 | 0.099* | |
H7D3 | −0.2293 | 0.6453 | −0.0423 | 0.099* | |
C1GE | −0.3183 (4) | 0.96374 (14) | 0.00453 (15) | 0.0520 (10) | |
C2GB | 0.5870 (3) | 0.69165 (16) | 0.17485 (14) | 0.0517 (10) | |
C7GE | −0.4449 (4) | 0.92519 (17) | −0.06814 (15) | 0.0645 (11) | |
H7E1 | −0.4567 | 0.9595 | −0.0830 | 0.097* | |
H7E2 | −0.5264 | 0.9035 | −0.0777 | 0.097* | |
H7E3 | −0.3631 | 0.9078 | −0.0766 | 0.097* | |
C7GB | 0.5925 (5) | 0.6435 (2) | 0.2042 (2) | 0.0956 (18) | |
H7B1 | 0.5868 | 0.6120 | 0.1851 | 0.143* | |
H7B2 | 0.5150 | 0.6439 | 0.2216 | 0.143* | |
H7B3 | 0.6794 | 0.6431 | 0.2251 | 0.143* | |
C4GE | −0.5036 (4) | 0.91838 (17) | 0.05397 (17) | 0.0657 (12) | |
H4GE | −0.5676 | 0.9025 | 0.0709 | 0.079* | |
C6GE | −0.3043 (4) | 0.97321 (15) | 0.05007 (14) | 0.0516 (10) | |
C8GB | 0.5866 (6) | 0.8404 (2) | 0.1862 (2) | 0.1025 (19) | |
H8B1 | 0.5735 | 0.8666 | 0.1619 | 0.154* | |
H8B2 | 0.6757 | 0.8462 | 0.2050 | 0.154* | |
H8B3 | 0.5126 | 0.8437 | 0.2048 | 0.154* | |
C8GD | −0.1387 (5) | 0.83846 (19) | −0.07990 (18) | 0.0830 (15) | |
H8D1 | −0.0482 | 0.8415 | −0.0613 | 0.125* | |
H8D2 | −0.2110 | 0.8442 | −0.0609 | 0.125* | |
H8D3 | −0.1470 | 0.8648 | −0.1041 | 0.125* | |
C3GE | −0.5165 (4) | 0.91023 (16) | 0.00758 (16) | 0.0617 (11) | |
H3GE | −0.5891 | 0.8887 | −0.0067 | 0.074* | |
C5GE | −0.3997 (5) | 0.94895 (17) | 0.07568 (16) | 0.0656 (12) | |
H5GE | −0.3910 | 0.9540 | 0.1075 | 0.079* | |
C8GE | −0.1918 (5) | 1.00692 (19) | 0.07502 (15) | 0.0750 (13) | |
H8E1 | −0.1018 | 0.9928 | 0.0705 | 0.112* | |
H8E2 | −0.1994 | 1.0070 | 0.1074 | 0.112* | |
H8E3 | −0.2010 | 1.0429 | 0.0633 | 0.112* | |
N1GA | 0.7727 (3) | 0.51557 (12) | 0.00316 (10) | 0.0408 (7) | |
C1GC | 1.0442 (3) | 0.48023 (13) | 0.21449 (11) | 0.0386 (8) | |
N1GC | 0.9616 (3) | 0.46946 (12) | 0.24895 (11) | 0.0441 (7) | |
C6GA | 0.5826 (3) | 0.54499 (14) | 0.04114 (12) | 0.0426 (8) | |
C5GA | 0.5130 (4) | 0.54082 (17) | 0.07846 (14) | 0.0558 (10) | |
H5GA | 0.4365 | 0.5632 | 0.0804 | 0.067* | |
C2GA | 0.7376 (4) | 0.47594 (15) | 0.07425 (12) | 0.0465 (9) | |
C6GC | 1.0046 (4) | 0.52186 (15) | 0.18453 (12) | 0.0488 (9) | |
C7GA | 0.8600 (4) | 0.44051 (16) | 0.07279 (14) | 0.0580 (10) | |
H7A1 | 0.8429 | 0.4178 | 0.0461 | 0.087* | |
H7A2 | 0.8745 | 0.4188 | 0.1002 | 0.087* | |
H7A3 | 0.9422 | 0.4619 | 0.0711 | 0.087* | |
C1GA | 0.6956 (3) | 0.51141 (13) | 0.03946 (11) | 0.0386 (8) | |
C8GA | 0.5387 (4) | 0.58380 (15) | 0.00438 (14) | 0.0563 (10) | |
H8A1 | 0.6100 | 0.6108 | 0.0044 | 0.085* | |
H8A2 | 0.4521 | 0.6003 | 0.0096 | 0.085* | |
H8A3 | 0.5251 | 0.5658 | −0.0249 | 0.085* | |
C2GC | 1.1572 (3) | 0.44827 (14) | 0.21009 (12) | 0.0423 (8) | |
C7GC | 1.1968 (4) | 0.40357 (14) | 0.24161 (13) | 0.0504 (9) | |
H7C1 | 1.2106 | 0.4164 | 0.2729 | 0.076* | |
H7C2 | 1.2825 | 0.3878 | 0.2347 | 0.076* | |
H7C3 | 1.1234 | 0.3771 | 0.2380 | 0.076* | |
C3GC | 1.2317 (4) | 0.45967 (18) | 0.17476 (14) | 0.0590 (11) | |
H3GC | 1.3088 | 0.4385 | 0.1709 | 0.071* | |
C8GC | 0.8829 (4) | 0.55609 (16) | 0.18897 (14) | 0.0612 (11) | |
H8C1 | 0.8020 | 0.5340 | 0.1909 | 0.092* | |
H8C2 | 0.8645 | 0.5791 | 0.1625 | 0.092* | |
H8C3 | 0.9026 | 0.5775 | 0.2165 | 0.092* | |
C3GA | 0.6640 (4) | 0.47347 (18) | 0.11052 (13) | 0.0606 (11) | |
H3GA | 0.6913 | 0.4493 | 0.1344 | 0.073* | |
C5GC | 1.0836 (4) | 0.5315 (2) | 0.15028 (14) | 0.0681 (13) | |
H5GC | 1.0594 | 0.5597 | 0.1299 | 0.082* | |
C4GA | 0.5515 (4) | 0.50554 (19) | 0.11245 (14) | 0.0660 (12) | |
H4GA | 0.5011 | 0.5031 | 0.1373 | 0.079* | |
C4GC | 1.1962 (4) | 0.5010 (2) | 0.14531 (15) | 0.0713 (13) | |
H4GC | 1.2492 | 0.5082 | 0.1218 | 0.086* | |
N1GF | 0.9800 (3) | 0.00363 (13) | 0.23781 (11) | 0.0450 (7) | |
C1GF | 1.0683 (3) | −0.00496 (14) | 0.20486 (11) | 0.0412 (8) | |
C5GF | 1.2618 (4) | 0.01866 (17) | 0.16874 (14) | 0.0566 (10) | |
H5GF | 1.3373 | 0.0412 | 0.1659 | 0.068* | |
C2GF | 1.0400 (4) | −0.04724 (15) | 0.17449 (12) | 0.0481 (9) | |
C6GF | 1.1783 (4) | 0.02941 (14) | 0.20180 (13) | 0.0462 (9) | |
C7GF | 0.9195 (4) | −0.08264 (16) | 0.17746 (14) | 0.0624 (11) | |
H7F1 | 0.9077 | −0.1067 | 0.1515 | 0.094* | |
H7F3 | 0.8359 | −0.0614 | 0.1772 | 0.094* | |
H7F2 | 0.9360 | −0.1029 | 0.2056 | 0.094* | |
C8GF | 1.2058 (4) | 0.07512 (15) | 0.23326 (15) | 0.0602 (11) | |
H8F1 | 1.1240 | 0.0976 | 0.2307 | 0.090* | |
H8F2 | 1.2839 | 0.0953 | 0.2253 | 0.090* | |
H8F3 | 1.2277 | 0.0624 | 0.2644 | 0.090* | |
C3GF | 1.1273 (4) | −0.05620 (17) | 0.14266 (13) | 0.0578 (11) | |
H3GF | 1.1106 | −0.0850 | 0.1224 | 0.069* | |
C4GF | 1.2376 (4) | −0.02376 (18) | 0.14018 (13) | 0.0622 (11) | |
H4GF | 1.2977 | −0.0306 | 0.1186 | 0.075* | |
H1D1 | −0.106 (5) | 0.7176 (16) | −0.0044 (14) | 0.089 (16)* | |
H1D2 | −0.096 (4) | 0.7776 (14) | −0.0139 (15) | 0.080 (16)* | |
H1B1 | 0.634 (6) | 0.7780 (17) | 0.2551 (19) | 0.13 (2)* | |
H1B2 | 0.630 (6) | 0.7139 (18) | 0.255 (2) | 0.14 (3)* | |
H1C1 | 1.020 (3) | 0.4542 (14) | 0.2729 (11) | 0.057 (12)* | |
H1A1 | 0.720 (4) | 0.5286 (15) | −0.0230 (11) | 0.061 (12)* | |
H1F1 | 1.017 (3) | 0.0245 (13) | 0.2602 (11) | 0.048 (11)* | |
H1E1 | −0.251 (5) | 0.982 (2) | −0.0507 (12) | 0.11 (2)* | |
H1F2 | 0.935 (3) | −0.0259 (12) | 0.2465 (12) | 0.052 (11)* | |
H1A2 | 0.818 (4) | 0.4860 (13) | −0.0055 (13) | 0.070 (13)* | |
H1E2 | −0.178 (3) | 1.0154 (12) | −0.0080 (12) | 0.058 (12)* | |
H1C2 | 0.924 (3) | 0.5015 (12) | 0.2616 (11) | 0.056 (11)* | |
H1X | −0.061 (3) | 0.5490 (14) | 0.0180 (13) | 0.067* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1X | 0.0444 (14) | 0.0424 (14) | 0.0591 (16) | −0.0015 (11) | 0.0196 (12) | −0.0149 (12) |
O1Y | 0.0511 (17) | 0.0485 (16) | 0.0722 (19) | −0.0006 (13) | 0.0219 (14) | −0.0092 (14) |
O2X | 0.0488 (16) | 0.0427 (15) | 0.0776 (19) | −0.0036 (13) | 0.0173 (14) | 0.0177 (14) |
C8X | 0.0239 (17) | 0.042 (2) | 0.059 (2) | −0.0020 (14) | 0.0135 (15) | −0.0035 (17) |
C7X | 0.0232 (16) | 0.0328 (17) | 0.0378 (18) | 0.0000 (13) | 0.0067 (13) | 0.0022 (14) |
C1Y | 0.0218 (16) | 0.050 (2) | 0.0419 (19) | 0.0004 (14) | 0.0057 (14) | 0.0042 (16) |
O2Y | 0.0466 (16) | 0.0492 (16) | 0.093 (2) | 0.0029 (13) | 0.0235 (15) | 0.0253 (15) |
C9X | 0.0322 (18) | 0.043 (2) | 0.060 (2) | 0.0038 (15) | 0.0217 (17) | −0.0071 (18) |
C11Y | 0.0251 (17) | 0.051 (2) | 0.047 (2) | −0.0029 (15) | 0.0086 (15) | 0.0054 (17) |
C12X | 0.0229 (16) | 0.0357 (18) | 0.048 (2) | 0.0039 (14) | 0.0054 (14) | −0.0022 (15) |
C12Y | 0.0245 (17) | 0.052 (2) | 0.043 (2) | 0.0034 (15) | 0.0079 (14) | 0.0037 (17) |
C14X | 0.0262 (17) | 0.0382 (19) | 0.049 (2) | −0.0043 (14) | 0.0083 (15) | 0.0020 (16) |
C7Y | 0.0224 (16) | 0.044 (2) | 0.051 (2) | 0.0033 (14) | 0.0109 (15) | 0.0148 (17) |
C1X | 0.0208 (15) | 0.0354 (18) | 0.0433 (19) | −0.0002 (13) | 0.0050 (14) | −0.0063 (14) |
C1GD | 0.0227 (17) | 0.068 (3) | 0.052 (2) | 0.0075 (17) | 0.0068 (16) | 0.006 (2) |
C10Y | 0.044 (2) | 0.036 (2) | 0.055 (2) | 0.0049 (16) | 0.0152 (17) | 0.0033 (17) |
C1GB | 0.0246 (17) | 0.068 (3) | 0.043 (2) | −0.0036 (16) | 0.0064 (15) | −0.0057 (19) |
C13X | 0.0266 (17) | 0.0280 (17) | 0.051 (2) | −0.0012 (13) | 0.0101 (15) | −0.0015 (15) |
C2X | 0.0284 (17) | 0.0397 (19) | 0.044 (2) | −0.0004 (14) | 0.0046 (15) | −0.0061 (15) |
C16Y | 0.0363 (19) | 0.042 (2) | 0.056 (2) | −0.0021 (16) | 0.0123 (17) | 0.0053 (17) |
N1GE | 0.0448 (19) | 0.044 (2) | 0.076 (3) | −0.0037 (16) | 0.0086 (18) | 0.0119 (18) |
C18Y | 0.0296 (19) | 0.067 (3) | 0.068 (3) | 0.0007 (18) | 0.0157 (18) | 0.021 (2) |
C2Y | 0.0272 (17) | 0.060 (2) | 0.045 (2) | 0.0021 (16) | 0.0058 (15) | 0.0095 (18) |
C15Y | 0.036 (2) | 0.054 (2) | 0.074 (3) | 0.0012 (17) | 0.0253 (19) | 0.014 (2) |
C16X | 0.041 (2) | 0.0342 (19) | 0.059 (2) | −0.0056 (16) | 0.0131 (17) | 0.0047 (17) |
C11X | 0.0298 (17) | 0.0364 (19) | 0.0424 (19) | −0.0019 (14) | 0.0048 (15) | −0.0041 (15) |
C18X | 0.0327 (19) | 0.050 (2) | 0.068 (3) | 0.0032 (16) | 0.0163 (18) | 0.008 (2) |
C10X | 0.0338 (18) | 0.0319 (18) | 0.0399 (19) | 0.0021 (14) | 0.0104 (15) | −0.0032 (15) |
C6X | 0.0265 (17) | 0.051 (2) | 0.051 (2) | −0.0060 (15) | 0.0015 (15) | −0.0096 (18) |
C13Y | 0.0252 (17) | 0.046 (2) | 0.0417 (19) | −0.0024 (14) | 0.0068 (14) | −0.0021 (16) |
C15X | 0.0293 (18) | 0.0374 (19) | 0.064 (2) | −0.0027 (15) | 0.0094 (16) | 0.0058 (17) |
C8Y | 0.0291 (19) | 0.048 (2) | 0.096 (3) | −0.0040 (16) | 0.022 (2) | −0.009 (2) |
C6GB | 0.033 (2) | 0.059 (3) | 0.066 (3) | −0.0031 (17) | 0.0154 (18) | −0.007 (2) |
C6Y | 0.0299 (19) | 0.060 (2) | 0.061 (2) | −0.0030 (17) | 0.0031 (17) | 0.015 (2) |
C5Y | 0.042 (2) | 0.065 (3) | 0.065 (3) | 0.0023 (19) | −0.0002 (19) | 0.003 (2) |
C5GD | 0.032 (2) | 0.084 (3) | 0.070 (3) | 0.012 (2) | 0.0047 (19) | 0.030 (3) |
C5X | 0.0327 (19) | 0.066 (3) | 0.046 (2) | 0.0009 (17) | −0.0005 (16) | −0.0027 (19) |
C5GB | 0.030 (2) | 0.080 (3) | 0.067 (3) | 0.0038 (19) | 0.0107 (19) | 0.018 (2) |
C6GD | 0.0273 (19) | 0.057 (3) | 0.075 (3) | 0.0065 (17) | 0.0094 (18) | 0.004 (2) |
C3GD | 0.031 (2) | 0.075 (3) | 0.057 (3) | −0.0016 (18) | 0.0067 (17) | −0.001 (2) |
C9Y | 0.036 (2) | 0.054 (2) | 0.097 (3) | −0.0018 (18) | 0.032 (2) | −0.009 (2) |
C4GD | 0.036 (2) | 0.086 (3) | 0.052 (2) | 0.001 (2) | 0.0003 (18) | 0.012 (2) |
C3X | 0.0357 (19) | 0.054 (2) | 0.041 (2) | −0.0002 (16) | 0.0080 (15) | −0.0024 (17) |
C4Y | 0.056 (2) | 0.073 (3) | 0.048 (2) | 0.007 (2) | 0.0044 (19) | 0.006 (2) |
N1GD | 0.053 (2) | 0.080 (3) | 0.056 (2) | 0.004 (2) | 0.0131 (18) | −0.006 (2) |
C14Y | 0.0291 (18) | 0.054 (2) | 0.064 (2) | 0.0043 (16) | 0.0174 (17) | 0.0080 (19) |
C3Y | 0.045 (2) | 0.066 (3) | 0.053 (2) | 0.0039 (19) | 0.0086 (18) | 0.005 (2) |
C2GD | 0.0244 (17) | 0.063 (3) | 0.051 (2) | 0.0042 (16) | 0.0070 (15) | 0.0042 (19) |
C17Y | 0.034 (2) | 0.059 (3) | 0.077 (3) | 0.0092 (18) | 0.0182 (19) | 0.020 (2) |
C4GB | 0.032 (2) | 0.110 (4) | 0.044 (2) | −0.001 (2) | 0.0025 (17) | −0.009 (3) |
C17X | 0.035 (2) | 0.054 (2) | 0.074 (3) | 0.0003 (17) | 0.0254 (19) | 0.012 (2) |
N1GB | 0.059 (2) | 0.127 (4) | 0.051 (2) | −0.013 (3) | 0.0157 (19) | −0.016 (3) |
C4X | 0.043 (2) | 0.072 (3) | 0.044 (2) | −0.0024 (19) | 0.0006 (17) | 0.000 (2) |
C3GB | 0.034 (2) | 0.068 (3) | 0.088 (3) | −0.0001 (19) | 0.011 (2) | −0.024 (3) |
C2GE | 0.040 (2) | 0.044 (2) | 0.072 (3) | 0.0080 (17) | 0.0128 (19) | 0.007 (2) |
C7GD | 0.063 (3) | 0.070 (3) | 0.068 (3) | 0.010 (2) | 0.018 (2) | 0.012 (2) |
C1GE | 0.046 (2) | 0.040 (2) | 0.071 (3) | 0.0074 (17) | 0.014 (2) | 0.0125 (19) |
C2GB | 0.0300 (19) | 0.060 (3) | 0.065 (3) | 0.0013 (17) | 0.0047 (18) | 0.001 (2) |
C7GE | 0.059 (3) | 0.061 (3) | 0.076 (3) | 0.002 (2) | 0.017 (2) | −0.001 (2) |
C7GB | 0.073 (3) | 0.082 (4) | 0.137 (5) | 0.014 (3) | 0.033 (3) | 0.045 (3) |
C4GE | 0.048 (2) | 0.063 (3) | 0.092 (4) | 0.006 (2) | 0.029 (2) | 0.019 (3) |
C6GE | 0.046 (2) | 0.044 (2) | 0.067 (3) | 0.0078 (18) | 0.014 (2) | 0.011 (2) |
C8GB | 0.102 (4) | 0.068 (3) | 0.147 (5) | −0.015 (3) | 0.051 (4) | −0.031 (4) |
C8GD | 0.070 (3) | 0.070 (3) | 0.114 (4) | 0.013 (3) | 0.029 (3) | 0.000 (3) |
C3GE | 0.055 (3) | 0.057 (3) | 0.076 (3) | 0.000 (2) | 0.019 (2) | 0.008 (2) |
C5GE | 0.066 (3) | 0.060 (3) | 0.074 (3) | 0.018 (2) | 0.019 (2) | 0.013 (2) |
C8GE | 0.084 (3) | 0.076 (3) | 0.064 (3) | 0.008 (3) | 0.007 (2) | 0.010 (2) |
N1GA | 0.0419 (17) | 0.0406 (18) | 0.0410 (18) | 0.0006 (14) | 0.0095 (14) | −0.0031 (14) |
C1GC | 0.0369 (19) | 0.044 (2) | 0.0351 (18) | −0.0063 (15) | 0.0064 (15) | −0.0005 (15) |
N1GC | 0.0445 (18) | 0.0435 (18) | 0.0469 (18) | 0.0047 (14) | 0.0154 (15) | 0.0022 (15) |
C6GA | 0.0326 (19) | 0.042 (2) | 0.053 (2) | −0.0032 (15) | 0.0059 (16) | −0.0032 (17) |
C5GA | 0.034 (2) | 0.067 (3) | 0.068 (3) | 0.0000 (18) | 0.0145 (19) | −0.010 (2) |
C2GA | 0.039 (2) | 0.055 (2) | 0.045 (2) | −0.0020 (17) | 0.0058 (16) | −0.0007 (18) |
C6GC | 0.044 (2) | 0.057 (2) | 0.044 (2) | −0.0082 (18) | 0.0016 (17) | 0.0041 (18) |
C7GA | 0.055 (2) | 0.056 (2) | 0.063 (3) | 0.011 (2) | 0.012 (2) | 0.010 (2) |
C1GA | 0.0331 (18) | 0.0385 (19) | 0.045 (2) | −0.0064 (15) | 0.0082 (15) | −0.0066 (16) |
C8GA | 0.041 (2) | 0.043 (2) | 0.085 (3) | 0.0025 (17) | 0.010 (2) | 0.001 (2) |
C2GC | 0.0353 (19) | 0.049 (2) | 0.043 (2) | −0.0078 (16) | 0.0056 (16) | −0.0047 (17) |
C7GC | 0.043 (2) | 0.050 (2) | 0.059 (2) | 0.0001 (17) | 0.0099 (18) | −0.0078 (19) |
C3GC | 0.038 (2) | 0.084 (3) | 0.058 (3) | −0.003 (2) | 0.0154 (19) | −0.008 (2) |
C8GC | 0.059 (3) | 0.059 (3) | 0.064 (3) | 0.008 (2) | 0.004 (2) | 0.011 (2) |
C3GA | 0.052 (2) | 0.082 (3) | 0.050 (2) | 0.003 (2) | 0.0136 (19) | 0.011 (2) |
C5GC | 0.051 (3) | 0.096 (4) | 0.057 (3) | −0.008 (2) | 0.007 (2) | 0.026 (2) |
C4GA | 0.049 (2) | 0.097 (4) | 0.056 (3) | 0.002 (2) | 0.025 (2) | 0.004 (2) |
C4GC | 0.052 (3) | 0.110 (4) | 0.055 (3) | −0.009 (3) | 0.014 (2) | 0.016 (3) |
N1GF | 0.0438 (18) | 0.0416 (19) | 0.053 (2) | −0.0019 (15) | 0.0164 (15) | −0.0032 (16) |
C1GF | 0.0376 (19) | 0.044 (2) | 0.043 (2) | 0.0054 (16) | 0.0095 (16) | 0.0047 (16) |
C5GF | 0.050 (2) | 0.063 (3) | 0.060 (3) | −0.007 (2) | 0.018 (2) | 0.009 (2) |
C2GF | 0.053 (2) | 0.049 (2) | 0.042 (2) | 0.0012 (18) | 0.0073 (18) | 0.0008 (17) |
C6GF | 0.039 (2) | 0.046 (2) | 0.054 (2) | 0.0037 (16) | 0.0088 (17) | 0.0065 (18) |
C7GF | 0.070 (3) | 0.053 (2) | 0.064 (3) | −0.011 (2) | 0.012 (2) | −0.011 (2) |
C8GF | 0.049 (2) | 0.050 (2) | 0.083 (3) | −0.0005 (19) | 0.013 (2) | −0.002 (2) |
C3GF | 0.069 (3) | 0.060 (3) | 0.046 (2) | 0.003 (2) | 0.014 (2) | −0.0026 (19) |
C4GF | 0.069 (3) | 0.077 (3) | 0.044 (2) | 0.008 (2) | 0.022 (2) | 0.005 (2) |
Geometric parameters (Å, º) top
O1X—C10X | 1.371 (4) | C3Y—H3Y2 | 0.9900 |
O1X—H1X | 0.949 (19) | C2GD—C7GD | 1.499 (5) |
O1Y—C10Y | 1.375 (4) | C17Y—H17Y | 0.9500 |
O1Y—H1Y | 0.94 (2) | C4GB—C3GB | 1.381 (6) |
O2X—C16X | 1.371 (4) | C4GB—H4GB | 0.9500 |
O2X—H2X | 0.91 (2) | C17X—H17X | 0.9500 |
C8X—C9X | 1.376 (5) | N1GB—H1B1 | 0.93 (3) |
C8X—C7X | 1.398 (4) | N1GB—H1B2 | 0.97 (3) |
C8X—H8X | 0.9500 | C4X—H4X1 | 0.9900 |
C7X—C12X | 1.394 (4) | C4X—H4X2 | 0.9900 |
C7X—C1X | 1.537 (4) | C3GB—C2GB | 1.372 (6) |
C1Y—C13Y | 1.522 (5) | C3GB—H3GB | 0.9500 |
C1Y—C7Y | 1.548 (5) | C2GE—C3GE | 1.364 (5) |
C1Y—C2Y | 1.558 (4) | C2GE—C1GE | 1.421 (5) |
C1Y—C6Y | 1.563 (5) | C2GE—C7GE | 1.494 (6) |
O2Y—C16Y | 1.370 (4) | C7GD—H7D1 | 0.9800 |
O2Y—H2Y | 0.95 (2) | C7GD—H7D2 | 0.9800 |
C9X—C10X | 1.378 (4) | C7GD—H7D3 | 0.9800 |
C9X—H9X | 0.9500 | C1GE—C6GE | 1.368 (6) |
C11Y—C10Y | 1.376 (5) | C2GB—C7GB | 1.505 (6) |
C11Y—C12Y | 1.385 (5) | C7GE—H7E1 | 0.9800 |
C11Y—H11Y | 0.9500 | C7GE—H7E2 | 0.9800 |
C12X—C11X | 1.393 (4) | C7GE—H7E3 | 0.9800 |
C12X—H12X | 0.9500 | C7GB—H7B1 | 0.9800 |
C12Y—C7Y | 1.391 (5) | C7GB—H7B2 | 0.9800 |
C12Y—H12Y | 0.9500 | C7GB—H7B3 | 0.9800 |
C14X—C13X | 1.391 (4) | C4GE—C5GE | 1.369 (6) |
C14X—C15X | 1.391 (5) | C4GE—C3GE | 1.388 (6) |
C14X—H14X | 0.9500 | C4GE—H4GE | 0.9500 |
C7Y—C8Y | 1.387 (5) | C6GE—C5GE | 1.431 (5) |
C1X—C13X | 1.535 (4) | C6GE—C8GE | 1.507 (6) |
C1X—C2X | 1.550 (4) | C8GB—H8B1 | 0.9800 |
C1X—C6X | 1.556 (4) | C8GB—H8B2 | 0.9800 |
C1GD—C2GD | 1.392 (5) | C8GB—H8B3 | 0.9800 |
C1GD—N1GD | 1.393 (5) | C8GD—H8D1 | 0.9800 |
C1GD—C6GD | 1.407 (5) | C8GD—H8D2 | 0.9800 |
C10Y—C9Y | 1.380 (5) | C8GD—H8D3 | 0.9800 |
C1GB—C2GB | 1.390 (5) | C3GE—H3GE | 0.9500 |
C1GB—C6GB | 1.394 (5) | C5GE—H5GE | 0.9500 |
C1GB—N1GB | 1.395 (5) | C8GE—H8E1 | 0.9800 |
C13X—C18X | 1.399 (4) | C8GE—H8E2 | 0.9800 |
C2X—C3X | 1.526 (5) | C8GE—H8E3 | 0.9800 |
C2X—H2X1 | 0.9900 | N1GA—C1GA | 1.411 (4) |
C2X—H2X2 | 0.9900 | N1GA—H1A1 | 0.94 (3) |
C16Y—C17Y | 1.376 (5) | N1GA—H1A2 | 0.93 (2) |
C16Y—C15Y | 1.382 (5) | C1GC—C2GC | 1.396 (5) |
N1GE—C1GE | 1.402 (5) | C1GC—C6GC | 1.405 (5) |
N1GE—H1E1 | 0.96 (3) | C1GC—N1GC | 1.424 (4) |
N1GE—H1E2 | 0.94 (2) | N1GC—H1C1 | 0.93 (3) |
C18Y—C17Y | 1.385 (5) | N1GC—H1C2 | 0.993 (19) |
C18Y—C13Y | 1.390 (5) | C6GA—C5GA | 1.391 (5) |
C18Y—H18Y | 0.9500 | C6GA—C1GA | 1.406 (5) |
C2Y—C3Y | 1.479 (5) | C6GA—C8GA | 1.493 (5) |
C2Y—H2Y1 | 0.9900 | C5GA—C4GA | 1.367 (6) |
C2Y—H2Y2 | 0.9900 | C5GA—H5GA | 0.9500 |
C15Y—C14Y | 1.380 (5) | C2GA—C3GA | 1.386 (5) |
C15Y—H15Y | 0.9500 | C2GA—C1GA | 1.393 (5) |
C16X—C17X | 1.379 (5) | C2GA—C7GA | 1.508 (5) |
C16X—C15X | 1.390 (5) | C6GC—C5GC | 1.391 (5) |
C11X—C10X | 1.375 (4) | C6GC—C8GC | 1.499 (5) |
C11X—H11X | 0.9500 | C7GA—H7A1 | 0.9800 |
C18X—C17X | 1.370 (5) | C7GA—H7A2 | 0.9800 |
C18X—H18X | 0.9500 | C7GA—H7A3 | 0.9800 |
C6X—C5X | 1.518 (5) | C8GA—H8A1 | 0.9800 |
C6X—H6X1 | 0.9900 | C8GA—H8A2 | 0.9800 |
C6X—H6X2 | 0.9900 | C8GA—H8A3 | 0.9800 |
C13Y—C14Y | 1.391 (4) | C2GC—C3GC | 1.397 (5) |
C15X—H15X | 0.9500 | C2GC—C7GC | 1.492 (5) |
C8Y—C9Y | 1.375 (5) | C7GC—H7C1 | 0.9800 |
C8Y—H8Y | 0.9500 | C7GC—H7C2 | 0.9800 |
C6GB—C5GB | 1.363 (6) | C7GC—H7C3 | 0.9800 |
C6GB—C8GB | 1.513 (6) | C3GC—C4GC | 1.383 (6) |
C6Y—C5Y | 1.502 (5) | C3GC—H3GC | 0.9500 |
C6Y—H6Y1 | 0.9900 | C8GC—H8C1 | 0.9800 |
C6Y—H6Y2 | 0.9900 | C8GC—H8C2 | 0.9800 |
C5Y—C4Y | 1.518 (5) | C8GC—H8C3 | 0.9800 |
C5Y—H5Y1 | 0.9900 | C3GA—C4GA | 1.380 (6) |
C5Y—H5Y2 | 0.9900 | C3GA—H3GA | 0.9500 |
C5GD—C4GD | 1.382 (6) | C5GC—C4GC | 1.375 (6) |
C5GD—C6GD | 1.391 (6) | C5GC—H5GC | 0.9500 |
C5GD—H5GD | 0.9500 | C4GA—H4GA | 0.9500 |
C5X—C4X | 1.521 (5) | C4GC—H4GC | 0.9500 |
C5X—H5X1 | 0.9900 | N1GF—C1GF | 1.418 (4) |
C5X—H5X2 | 0.9900 | N1GF—H1F1 | 0.89 (3) |
C5GB—C4GB | 1.369 (6) | N1GF—H1F2 | 0.93 (2) |
C5GB—H5GB | 0.9500 | C1GF—C6GF | 1.402 (5) |
C6GD—C8GD | 1.492 (6) | C1GF—C2GF | 1.409 (5) |
C3GD—C4GD | 1.367 (6) | C5GF—C4GF | 1.375 (6) |
C3GD—C2GD | 1.388 (5) | C5GF—C6GF | 1.397 (5) |
C3GD—H3GD | 0.9500 | C5GF—H5GF | 0.9500 |
C9Y—H9Y | 0.9500 | C2GF—C3GF | 1.386 (5) |
C4GD—H4GD | 0.9500 | C2GF—C7GF | 1.500 (5) |
C3X—C4X | 1.521 (5) | C6GF—C8GF | 1.495 (5) |
C3X—H3X1 | 0.9900 | C7GF—H7F1 | 0.9800 |
C3X—H3X2 | 0.9900 | C7GF—H7F3 | 0.9800 |
C4Y—C3Y | 1.523 (5) | C7GF—H7F2 | 0.9800 |
C4Y—H4Y1 | 0.9900 | C8GF—H8F1 | 0.9800 |
C4Y—H4Y2 | 0.9900 | C8GF—H8F2 | 0.9800 |
N1GD—H1D1 | 0.98 (3) | C8GF—H8F3 | 0.9800 |
N1GD—H1D2 | 0.92 (3) | C3GF—C4GF | 1.372 (6) |
C14Y—H14Y | 0.9500 | C3GF—H3GF | 0.9500 |
C3Y—H3Y1 | 0.9900 | C4GF—H4GF | 0.9500 |
| | | |
C10X—O1X—H1X | 115 (2) | C5GB—C4GB—H4GB | 120.2 |
C10Y—O1Y—H1Y | 120 (3) | C3GB—C4GB—H4GB | 120.2 |
C16X—O2X—H2X | 115 (3) | C18X—C17X—C16X | 121.3 (3) |
C9X—C8X—C7X | 122.2 (3) | C18X—C17X—H17X | 119.3 |
C9X—C8X—H8X | 118.9 | C16X—C17X—H17X | 119.3 |
C7X—C8X—H8X | 118.9 | C1GB—N1GB—H1B1 | 121 (4) |
C12X—C7X—C8X | 115.6 (3) | C1GB—N1GB—H1B2 | 109 (4) |
C12X—C7X—C1X | 121.9 (3) | H1B1—N1GB—H1B2 | 118 (6) |
C8X—C7X—C1X | 122.3 (3) | C5X—C4X—C3X | 109.9 (3) |
C13Y—C1Y—C7Y | 108.4 (3) | C5X—C4X—H4X1 | 109.7 |
C13Y—C1Y—C2Y | 110.8 (3) | C3X—C4X—H4X1 | 109.7 |
C7Y—C1Y—C2Y | 111.3 (3) | C5X—C4X—H4X2 | 109.7 |
C13Y—C1Y—C6Y | 108.7 (3) | C3X—C4X—H4X2 | 109.7 |
C7Y—C1Y—C6Y | 112.6 (3) | H4X1—C4X—H4X2 | 108.2 |
C2Y—C1Y—C6Y | 104.9 (3) | C2GB—C3GB—C4GB | 120.9 (4) |
C16Y—O2Y—H2Y | 109 (3) | C2GB—C3GB—H3GB | 119.6 |
C8X—C9X—C10X | 120.8 (3) | C4GB—C3GB—H3GB | 119.6 |
C8X—C9X—H9X | 119.6 | C3GE—C2GE—C1GE | 117.9 (4) |
C10X—C9X—H9X | 119.6 | C3GE—C2GE—C7GE | 121.1 (4) |
C10Y—C11Y—C12Y | 119.6 (3) | C1GE—C2GE—C7GE | 120.9 (4) |
C10Y—C11Y—H11Y | 120.2 | C2GD—C7GD—H7D1 | 109.5 |
C12Y—C11Y—H11Y | 120.2 | C2GD—C7GD—H7D2 | 109.5 |
C11X—C12X—C7X | 122.6 (3) | H7D1—C7GD—H7D2 | 109.5 |
C11X—C12X—H12X | 118.7 | C2GD—C7GD—H7D3 | 109.5 |
C7X—C12X—H12X | 118.7 | H7D1—C7GD—H7D3 | 109.5 |
C11Y—C12Y—C7Y | 122.5 (3) | H7D2—C7GD—H7D3 | 109.5 |
C11Y—C12Y—H12Y | 118.7 | C6GE—C1GE—N1GE | 117.2 (4) |
C7Y—C12Y—H12Y | 118.7 | C6GE—C1GE—C2GE | 121.9 (4) |
C13X—C14X—C15X | 122.9 (3) | N1GE—C1GE—C2GE | 120.7 (4) |
C13X—C14X—H14X | 118.6 | C3GB—C2GB—C1GB | 118.8 (4) |
C15X—C14X—H14X | 118.6 | C3GB—C2GB—C7GB | 120.0 (4) |
C8Y—C7Y—C12Y | 116.1 (3) | C1GB—C2GB—C7GB | 121.1 (4) |
C8Y—C7Y—C1Y | 121.8 (3) | C2GE—C7GE—H7E1 | 109.5 |
C12Y—C7Y—C1Y | 122.0 (3) | C2GE—C7GE—H7E2 | 109.5 |
C13X—C1X—C7X | 106.1 (3) | H7E1—C7GE—H7E2 | 109.5 |
C13X—C1X—C2X | 111.0 (2) | C2GE—C7GE—H7E3 | 109.5 |
C7X—C1X—C2X | 111.6 (2) | H7E1—C7GE—H7E3 | 109.5 |
C13X—C1X—C6X | 110.5 (3) | H7E2—C7GE—H7E3 | 109.5 |
C7X—C1X—C6X | 111.5 (3) | C2GB—C7GB—H7B1 | 109.5 |
C2X—C1X—C6X | 106.2 (3) | C2GB—C7GB—H7B2 | 109.5 |
C2GD—C1GD—N1GD | 120.1 (4) | H7B1—C7GB—H7B2 | 109.5 |
C2GD—C1GD—C6GD | 120.1 (4) | C2GB—C7GB—H7B3 | 109.5 |
N1GD—C1GD—C6GD | 119.8 (4) | H7B1—C7GB—H7B3 | 109.5 |
O1Y—C10Y—C11Y | 121.8 (3) | H7B2—C7GB—H7B3 | 109.5 |
O1Y—C10Y—C9Y | 119.0 (3) | C5GE—C4GE—C3GE | 120.8 (4) |
C11Y—C10Y—C9Y | 119.2 (3) | C5GE—C4GE—H4GE | 119.6 |
C2GB—C1GB—C6GB | 120.3 (4) | C3GE—C4GE—H4GE | 119.6 |
C2GB—C1GB—N1GB | 119.2 (4) | C1GE—C6GE—C5GE | 118.4 (4) |
C6GB—C1GB—N1GB | 120.5 (4) | C1GE—C6GE—C8GE | 123.5 (4) |
C14X—C13X—C18X | 115.5 (3) | C5GE—C6GE—C8GE | 118.1 (4) |
C14X—C13X—C1X | 122.6 (3) | C6GB—C8GB—H8B1 | 109.5 |
C18X—C13X—C1X | 121.9 (3) | C6GB—C8GB—H8B2 | 109.5 |
C3X—C2X—C1X | 113.5 (3) | H8B1—C8GB—H8B2 | 109.5 |
C3X—C2X—H2X1 | 108.9 | C6GB—C8GB—H8B3 | 109.5 |
C1X—C2X—H2X1 | 108.9 | H8B1—C8GB—H8B3 | 109.5 |
C3X—C2X—H2X2 | 108.9 | H8B2—C8GB—H8B3 | 109.5 |
C1X—C2X—H2X2 | 108.9 | C6GD—C8GD—H8D1 | 109.5 |
H2X1—C2X—H2X2 | 107.7 | C6GD—C8GD—H8D2 | 109.5 |
O2Y—C16Y—C17Y | 122.4 (3) | H8D1—C8GD—H8D2 | 109.5 |
O2Y—C16Y—C15Y | 119.1 (3) | C6GD—C8GD—H8D3 | 109.5 |
C17Y—C16Y—C15Y | 118.5 (3) | H8D1—C8GD—H8D3 | 109.5 |
C1GE—N1GE—H1E1 | 107 (3) | H8D2—C8GD—H8D3 | 109.5 |
C1GE—N1GE—H1E2 | 114 (2) | C2GE—C3GE—C4GE | 121.5 (4) |
H1E1—N1GE—H1E2 | 116 (4) | C2GE—C3GE—H3GE | 119.3 |
C17Y—C18Y—C13Y | 123.2 (3) | C4GE—C3GE—H3GE | 119.3 |
C17Y—C18Y—H18Y | 118.4 | C4GE—C5GE—C6GE | 119.5 (4) |
C13Y—C18Y—H18Y | 118.4 | C4GE—C5GE—H5GE | 120.3 |
C3Y—C2Y—C1Y | 115.4 (3) | C6GE—C5GE—H5GE | 120.3 |
C3Y—C2Y—H2Y1 | 108.4 | C6GE—C8GE—H8E1 | 109.5 |
C1Y—C2Y—H2Y1 | 108.4 | C6GE—C8GE—H8E2 | 109.5 |
C3Y—C2Y—H2Y2 | 108.4 | H8E1—C8GE—H8E2 | 109.5 |
C1Y—C2Y—H2Y2 | 108.4 | C6GE—C8GE—H8E3 | 109.5 |
H2Y1—C2Y—H2Y2 | 107.5 | H8E1—C8GE—H8E3 | 109.5 |
C14Y—C15Y—C16Y | 120.9 (3) | H8E2—C8GE—H8E3 | 109.5 |
C14Y—C15Y—H15Y | 119.6 | C1GA—N1GA—H1A1 | 112 (2) |
C16Y—C15Y—H15Y | 119.6 | C1GA—N1GA—H1A2 | 119 (3) |
O2X—C16X—C17X | 118.1 (3) | H1A1—N1GA—H1A2 | 107 (3) |
O2X—C16X—C15X | 123.6 (3) | C2GC—C1GC—C6GC | 122.0 (3) |
C17X—C16X—C15X | 118.3 (3) | C2GC—C1GC—N1GC | 119.8 (3) |
C10X—C11X—C12X | 119.7 (3) | C6GC—C1GC—N1GC | 118.1 (3) |
C10X—C11X—H11X | 120.1 | C1GC—N1GC—H1C1 | 107 (2) |
C12X—C11X—H11X | 120.1 | C1GC—N1GC—H1C2 | 114 (2) |
C17X—C18X—C13X | 122.3 (3) | H1C1—N1GC—H1C2 | 106 (3) |
C17X—C18X—H18X | 118.9 | C5GA—C6GA—C1GA | 117.5 (3) |
C13X—C18X—H18X | 118.9 | C5GA—C6GA—C8GA | 121.0 (3) |
O1X—C10X—C11X | 122.4 (3) | C1GA—C6GA—C8GA | 121.4 (3) |
O1X—C10X—C9X | 118.5 (3) | C4GA—C5GA—C6GA | 121.9 (4) |
C11X—C10X—C9X | 119.1 (3) | C4GA—C5GA—H5GA | 119.0 |
C5X—C6X—C1X | 113.4 (3) | C6GA—C5GA—H5GA | 119.0 |
C5X—C6X—H6X1 | 108.9 | C3GA—C2GA—C1GA | 118.7 (3) |
C1X—C6X—H6X1 | 108.9 | C3GA—C2GA—C7GA | 120.1 (4) |
C5X—C6X—H6X2 | 108.9 | C1GA—C2GA—C7GA | 121.2 (3) |
C1X—C6X—H6X2 | 108.9 | C5GC—C6GC—C1GC | 118.0 (4) |
H6X1—C6X—H6X2 | 107.7 | C5GC—C6GC—C8GC | 119.8 (4) |
C18Y—C13Y—C14Y | 115.3 (3) | C1GC—C6GC—C8GC | 122.2 (3) |
C18Y—C13Y—C1Y | 122.7 (3) | C2GA—C7GA—H7A1 | 109.5 |
C14Y—C13Y—C1Y | 121.9 (3) | C2GA—C7GA—H7A2 | 109.5 |
C16X—C15X—C14X | 119.6 (3) | H7A1—C7GA—H7A2 | 109.5 |
C16X—C15X—H15X | 120.2 | C2GA—C7GA—H7A3 | 109.5 |
C14X—C15X—H15X | 120.2 | H7A1—C7GA—H7A3 | 109.5 |
C9Y—C8Y—C7Y | 122.2 (3) | H7A2—C7GA—H7A3 | 109.5 |
C9Y—C8Y—H8Y | 118.9 | C2GA—C1GA—C6GA | 121.1 (3) |
C7Y—C8Y—H8Y | 118.9 | C2GA—C1GA—N1GA | 119.2 (3) |
C5GB—C6GB—C1GB | 119.2 (4) | C6GA—C1GA—N1GA | 119.6 (3) |
C5GB—C6GB—C8GB | 120.5 (4) | C6GA—C8GA—H8A1 | 109.5 |
C1GB—C6GB—C8GB | 120.3 (4) | C6GA—C8GA—H8A2 | 109.5 |
C5Y—C6Y—C1Y | 113.5 (3) | H8A1—C8GA—H8A2 | 109.5 |
C5Y—C6Y—H6Y1 | 108.9 | C6GA—C8GA—H8A3 | 109.5 |
C1Y—C6Y—H6Y1 | 108.9 | H8A1—C8GA—H8A3 | 109.5 |
C5Y—C6Y—H6Y2 | 108.9 | H8A2—C8GA—H8A3 | 109.5 |
C1Y—C6Y—H6Y2 | 108.9 | C1GC—C2GC—C3GC | 117.3 (3) |
H6Y1—C6Y—H6Y2 | 107.7 | C1GC—C2GC—C7GC | 121.6 (3) |
C6Y—C5Y—C4Y | 111.5 (3) | C3GC—C2GC—C7GC | 121.1 (3) |
C6Y—C5Y—H5Y1 | 109.3 | C2GC—C7GC—H7C1 | 109.5 |
C4Y—C5Y—H5Y1 | 109.3 | C2GC—C7GC—H7C2 | 109.5 |
C6Y—C5Y—H5Y2 | 109.3 | H7C1—C7GC—H7C2 | 109.5 |
C4Y—C5Y—H5Y2 | 109.3 | C2GC—C7GC—H7C3 | 109.5 |
H5Y1—C5Y—H5Y2 | 108.0 | H7C1—C7GC—H7C3 | 109.5 |
C4GD—C5GD—C6GD | 121.7 (4) | H7C2—C7GC—H7C3 | 109.5 |
C4GD—C5GD—H5GD | 119.2 | C4GC—C3GC—C2GC | 121.8 (4) |
C6GD—C5GD—H5GD | 119.2 | C4GC—C3GC—H3GC | 119.1 |
C6X—C5X—C4X | 111.9 (3) | C2GC—C3GC—H3GC | 119.1 |
C6X—C5X—H5X1 | 109.2 | C6GC—C8GC—H8C1 | 109.5 |
C4X—C5X—H5X1 | 109.2 | C6GC—C8GC—H8C2 | 109.5 |
C6X—C5X—H5X2 | 109.2 | H8C1—C8GC—H8C2 | 109.5 |
C4X—C5X—H5X2 | 109.2 | C6GC—C8GC—H8C3 | 109.5 |
H5X1—C5X—H5X2 | 107.9 | H8C1—C8GC—H8C3 | 109.5 |
C6GB—C5GB—C4GB | 121.2 (4) | H8C2—C8GC—H8C3 | 109.5 |
C6GB—C5GB—H5GB | 119.4 | C4GA—C3GA—C2GA | 121.0 (4) |
C4GB—C5GB—H5GB | 119.4 | C4GA—C3GA—H3GA | 119.5 |
C5GD—C6GD—C1GD | 118.5 (4) | C2GA—C3GA—H3GA | 119.5 |
C5GD—C6GD—C8GD | 121.5 (4) | C4GC—C5GC—C6GC | 121.4 (4) |
C1GD—C6GD—C8GD | 120.0 (4) | C4GC—C5GC—H5GC | 119.3 |
C4GD—C3GD—C2GD | 122.0 (4) | C6GC—C5GC—H5GC | 119.3 |
C4GD—C3GD—H3GD | 119.0 | C5GA—C4GA—C3GA | 119.7 (4) |
C2GD—C3GD—H3GD | 119.0 | C5GA—C4GA—H4GA | 120.2 |
C8Y—C9Y—C10Y | 120.4 (3) | C3GA—C4GA—H4GA | 120.2 |
C8Y—C9Y—H9Y | 119.8 | C5GC—C4GC—C3GC | 119.6 (4) |
C10Y—C9Y—H9Y | 119.8 | C5GC—C4GC—H4GC | 120.2 |
C3GD—C4GD—C5GD | 118.7 (4) | C3GC—C4GC—H4GC | 120.2 |
C3GD—C4GD—H4GD | 120.6 | C1GF—N1GF—H1F1 | 113 (2) |
C5GD—C4GD—H4GD | 120.6 | C1GF—N1GF—H1F2 | 116 (2) |
C4X—C3X—C2X | 111.5 (3) | H1F1—N1GF—H1F2 | 116 (3) |
C4X—C3X—H3X1 | 109.3 | C6GF—C1GF—C2GF | 121.1 (3) |
C2X—C3X—H3X1 | 109.3 | C6GF—C1GF—N1GF | 120.1 (3) |
C4X—C3X—H3X2 | 109.3 | C2GF—C1GF—N1GF | 118.7 (3) |
C2X—C3X—H3X2 | 109.3 | C4GF—C5GF—C6GF | 121.7 (4) |
H3X1—C3X—H3X2 | 108.0 | C4GF—C5GF—H5GF | 119.2 |
C5Y—C4Y—C3Y | 110.0 (3) | C6GF—C5GF—H5GF | 119.2 |
C5Y—C4Y—H4Y1 | 109.7 | C3GF—C2GF—C1GF | 118.9 (4) |
C3Y—C4Y—H4Y1 | 109.7 | C3GF—C2GF—C7GF | 120.8 (4) |
C5Y—C4Y—H4Y2 | 109.7 | C1GF—C2GF—C7GF | 120.3 (3) |
C3Y—C4Y—H4Y2 | 109.7 | C5GF—C6GF—C1GF | 117.3 (3) |
H4Y1—C4Y—H4Y2 | 108.2 | C5GF—C6GF—C8GF | 121.6 (3) |
C1GD—N1GD—H1D1 | 122 (3) | C1GF—C6GF—C8GF | 121.1 (3) |
C1GD—N1GD—H1D2 | 116 (3) | C2GF—C7GF—H7F1 | 109.5 |
H1D1—N1GD—H1D2 | 111 (4) | C2GF—C7GF—H7F3 | 109.5 |
C15Y—C14Y—C13Y | 122.2 (3) | H7F1—C7GF—H7F3 | 109.5 |
C15Y—C14Y—H14Y | 118.9 | C2GF—C7GF—H7F2 | 109.5 |
C13Y—C14Y—H14Y | 118.9 | H7F1—C7GF—H7F2 | 109.5 |
C2Y—C3Y—C4Y | 110.7 (3) | H7F3—C7GF—H7F2 | 109.5 |
C2Y—C3Y—H3Y1 | 109.5 | C6GF—C8GF—H8F1 | 109.5 |
C4Y—C3Y—H3Y1 | 109.5 | C6GF—C8GF—H8F2 | 109.5 |
C2Y—C3Y—H3Y2 | 109.5 | H8F1—C8GF—H8F2 | 109.5 |
C4Y—C3Y—H3Y2 | 109.5 | C6GF—C8GF—H8F3 | 109.5 |
H3Y1—C3Y—H3Y2 | 108.1 | H8F1—C8GF—H8F3 | 109.5 |
C3GD—C2GD—C1GD | 119.0 (4) | H8F2—C8GF—H8F3 | 109.5 |
C3GD—C2GD—C7GD | 120.7 (4) | C4GF—C3GF—C2GF | 120.5 (4) |
C1GD—C2GD—C7GD | 120.3 (3) | C4GF—C3GF—H3GF | 119.7 |
C16Y—C17Y—C18Y | 119.8 (3) | C2GF—C3GF—H3GF | 119.7 |
C16Y—C17Y—H17Y | 120.1 | C3GF—C4GF—C5GF | 120.4 (4) |
C18Y—C17Y—H17Y | 120.1 | C3GF—C4GF—H4GF | 119.8 |
C5GB—C4GB—C3GB | 119.6 (4) | C5GF—C4GF—H4GF | 119.8 |
| | | |
C9X—C8X—C7X—C12X | 0.1 (5) | C6Y—C5Y—C4Y—C3Y | −56.2 (5) |
C9X—C8X—C7X—C1X | −176.0 (3) | C16Y—C15Y—C14Y—C13Y | −0.9 (6) |
C7X—C8X—C9X—C10X | −1.2 (5) | C18Y—C13Y—C14Y—C15Y | −2.1 (5) |
C8X—C7X—C12X—C11X | 0.7 (5) | C1Y—C13Y—C14Y—C15Y | 176.4 (3) |
C1X—C7X—C12X—C11X | 176.8 (3) | C1Y—C2Y—C3Y—C4Y | −58.0 (4) |
C10Y—C11Y—C12Y—C7Y | 0.5 (5) | C5Y—C4Y—C3Y—C2Y | 55.5 (5) |
C11Y—C12Y—C7Y—C8Y | −2.0 (5) | C4GD—C3GD—C2GD—C1GD | −0.5 (5) |
C11Y—C12Y—C7Y—C1Y | 179.4 (3) | C4GD—C3GD—C2GD—C7GD | 179.2 (3) |
C13Y—C1Y—C7Y—C8Y | −85.7 (4) | N1GD—C1GD—C2GD—C3GD | 179.1 (3) |
C2Y—C1Y—C7Y—C8Y | 152.1 (3) | C6GD—C1GD—C2GD—C3GD | 1.1 (5) |
C6Y—C1Y—C7Y—C8Y | 34.6 (4) | N1GD—C1GD—C2GD—C7GD | −0.6 (5) |
C13Y—C1Y—C7Y—C12Y | 92.8 (3) | C6GD—C1GD—C2GD—C7GD | −178.6 (3) |
C2Y—C1Y—C7Y—C12Y | −29.4 (4) | O2Y—C16Y—C17Y—C18Y | 177.8 (4) |
C6Y—C1Y—C7Y—C12Y | −146.9 (3) | C15Y—C16Y—C17Y—C18Y | −2.6 (6) |
C12X—C7X—C1X—C13X | −91.2 (3) | C13Y—C18Y—C17Y—C16Y | −0.5 (6) |
C8X—C7X—C1X—C13X | 84.6 (3) | C6GB—C5GB—C4GB—C3GB | 0.8 (6) |
C12X—C7X—C1X—C2X | 29.9 (4) | C13X—C18X—C17X—C16X | 0.2 (6) |
C8X—C7X—C1X—C2X | −154.3 (3) | O2X—C16X—C17X—C18X | 176.8 (4) |
C12X—C7X—C1X—C6X | 148.4 (3) | C15X—C16X—C17X—C18X | −3.0 (6) |
C8X—C7X—C1X—C6X | −35.8 (4) | C6X—C5X—C4X—C3X | 55.2 (4) |
C12Y—C11Y—C10Y—O1Y | −177.4 (3) | C2X—C3X—C4X—C5X | −55.1 (4) |
C12Y—C11Y—C10Y—C9Y | 1.9 (5) | C5GB—C4GB—C3GB—C2GB | −0.4 (6) |
C15X—C14X—C13X—C18X | −3.4 (5) | C3GE—C2GE—C1GE—C6GE | −2.2 (6) |
C15X—C14X—C13X—C1X | 179.7 (3) | C7GE—C2GE—C1GE—C6GE | 176.5 (4) |
C7X—C1X—C13X—C14X | 96.1 (3) | C3GE—C2GE—C1GE—N1GE | 173.2 (3) |
C2X—C1X—C13X—C14X | −25.4 (4) | C7GE—C2GE—C1GE—N1GE | −8.1 (5) |
C6X—C1X—C13X—C14X | −142.9 (3) | C4GB—C3GB—C2GB—C1GB | −0.5 (5) |
C7X—C1X—C13X—C18X | −80.7 (4) | C4GB—C3GB—C2GB—C7GB | 179.1 (4) |
C2X—C1X—C13X—C18X | 157.9 (3) | C6GB—C1GB—C2GB—C3GB | 1.1 (5) |
C6X—C1X—C13X—C18X | 40.3 (4) | N1GB—C1GB—C2GB—C3GB | 179.2 (3) |
C13X—C1X—C2X—C3X | −175.2 (3) | C6GB—C1GB—C2GB—C7GB | −178.5 (4) |
C7X—C1X—C2X—C3X | 66.6 (3) | N1GB—C1GB—C2GB—C7GB | −0.4 (5) |
C6X—C1X—C2X—C3X | −55.1 (3) | N1GE—C1GE—C6GE—C5GE | −173.0 (3) |
C13Y—C1Y—C2Y—C3Y | 172.0 (3) | C2GE—C1GE—C6GE—C5GE | 2.5 (5) |
C7Y—C1Y—C2Y—C3Y | −67.2 (4) | N1GE—C1GE—C6GE—C8GE | 5.6 (6) |
C6Y—C1Y—C2Y—C3Y | 54.9 (4) | C2GE—C1GE—C6GE—C8GE | −178.9 (4) |
O2Y—C16Y—C15Y—C14Y | −177.1 (4) | C1GE—C2GE—C3GE—C4GE | 1.1 (6) |
C17Y—C16Y—C15Y—C14Y | 3.3 (6) | C7GE—C2GE—C3GE—C4GE | −177.6 (4) |
C7X—C12X—C11X—C10X | −0.4 (5) | C5GE—C4GE—C3GE—C2GE | −0.4 (6) |
C14X—C13X—C18X—C17X | 2.9 (5) | C3GE—C4GE—C5GE—C6GE | 0.7 (6) |
C1X—C13X—C18X—C17X | 179.9 (3) | C1GE—C6GE—C5GE—C4GE | −1.8 (6) |
C12X—C11X—C10X—O1X | 177.3 (3) | C8GE—C6GE—C5GE—C4GE | 179.6 (4) |
C12X—C11X—C10X—C9X | −0.7 (5) | C1GA—C6GA—C5GA—C4GA | −0.1 (6) |
C8X—C9X—C10X—O1X | −176.6 (3) | C8GA—C6GA—C5GA—C4GA | 179.9 (4) |
C8X—C9X—C10X—C11X | 1.5 (5) | C2GC—C1GC—C6GC—C5GC | −1.4 (5) |
C13X—C1X—C6X—C5X | 175.4 (3) | N1GC—C1GC—C6GC—C5GC | −178.5 (3) |
C7X—C1X—C6X—C5X | −66.8 (4) | C2GC—C1GC—C6GC—C8GC | 179.6 (3) |
C2X—C1X—C6X—C5X | 54.9 (4) | N1GC—C1GC—C6GC—C8GC | 2.5 (5) |
C17Y—C18Y—C13Y—C14Y | 2.8 (6) | C3GA—C2GA—C1GA—C6GA | 1.2 (5) |
C17Y—C18Y—C13Y—C1Y | −175.7 (4) | C7GA—C2GA—C1GA—C6GA | −179.1 (3) |
C7Y—C1Y—C13Y—C18Y | −107.2 (4) | C3GA—C2GA—C1GA—N1GA | 177.8 (3) |
C2Y—C1Y—C13Y—C18Y | 15.2 (5) | C7GA—C2GA—C1GA—N1GA | −2.5 (5) |
C6Y—C1Y—C13Y—C18Y | 130.0 (4) | C5GA—C6GA—C1GA—C2GA | −1.0 (5) |
C7Y—C1Y—C13Y—C14Y | 74.4 (4) | C8GA—C6GA—C1GA—C2GA | 178.9 (3) |
C2Y—C1Y—C13Y—C14Y | −163.2 (3) | C5GA—C6GA—C1GA—N1GA | −177.6 (3) |
C6Y—C1Y—C13Y—C14Y | −48.4 (4) | C8GA—C6GA—C1GA—N1GA | 2.3 (5) |
O2X—C16X—C15X—C14X | −177.3 (3) | C6GC—C1GC—C2GC—C3GC | 0.8 (5) |
C17X—C16X—C15X—C14X | 2.5 (5) | N1GC—C1GC—C2GC—C3GC | 178.0 (3) |
C13X—C14X—C15X—C16X | 0.7 (5) | C6GC—C1GC—C2GC—C7GC | −178.9 (3) |
C12Y—C7Y—C8Y—C9Y | 1.1 (6) | N1GC—C1GC—C2GC—C7GC | −1.8 (5) |
C1Y—C7Y—C8Y—C9Y | 179.7 (4) | C1GC—C2GC—C3GC—C4GC | 0.3 (6) |
C2GB—C1GB—C6GB—C5GB | −0.7 (5) | C7GC—C2GC—C3GC—C4GC | −180.0 (4) |
N1GB—C1GB—C6GB—C5GB | −178.8 (3) | C1GA—C2GA—C3GA—C4GA | −0.2 (6) |
C2GB—C1GB—C6GB—C8GB | 178.9 (4) | C7GA—C2GA—C3GA—C4GA | −179.9 (4) |
N1GB—C1GB—C6GB—C8GB | 0.8 (5) | C1GC—C6GC—C5GC—C4GC | 0.8 (6) |
C13Y—C1Y—C6Y—C5Y | −172.6 (3) | C8GC—C6GC—C5GC—C4GC | 179.8 (4) |
C7Y—C1Y—C6Y—C5Y | 67.3 (4) | C6GA—C5GA—C4GA—C3GA | 1.1 (7) |
C2Y—C1Y—C6Y—C5Y | −54.0 (4) | C2GA—C3GA—C4GA—C5GA | −0.9 (7) |
C1Y—C6Y—C5Y—C4Y | 58.1 (5) | C6GC—C5GC—C4GC—C3GC | 0.3 (7) |
C1X—C6X—C5X—C4X | −57.5 (4) | C2GC—C3GC—C4GC—C5GC | −0.8 (7) |
C1GB—C6GB—C5GB—C4GB | −0.2 (5) | C6GF—C1GF—C2GF—C3GF | 3.3 (5) |
C8GB—C6GB—C5GB—C4GB | −179.8 (4) | N1GF—C1GF—C2GF—C3GF | −179.1 (3) |
C4GD—C5GD—C6GD—C1GD | −0.1 (5) | C6GF—C1GF—C2GF—C7GF | −178.2 (3) |
C4GD—C5GD—C6GD—C8GD | 177.8 (4) | N1GF—C1GF—C2GF—C7GF | −0.6 (5) |
C2GD—C1GD—C6GD—C5GD | −0.7 (5) | C4GF—C5GF—C6GF—C1GF | 0.2 (6) |
N1GD—C1GD—C6GD—C5GD | −178.8 (3) | C4GF—C5GF—C6GF—C8GF | 179.2 (4) |
C2GD—C1GD—C6GD—C8GD | −178.7 (3) | C2GF—C1GF—C6GF—C5GF | −2.7 (5) |
N1GD—C1GD—C6GD—C8GD | 3.3 (5) | N1GF—C1GF—C6GF—C5GF | 179.7 (3) |
C7Y—C8Y—C9Y—C10Y | 1.3 (7) | C2GF—C1GF—C6GF—C8GF | 178.3 (3) |
O1Y—C10Y—C9Y—C8Y | 176.5 (4) | N1GF—C1GF—C6GF—C8GF | 0.7 (5) |
C11Y—C10Y—C9Y—C8Y | −2.9 (6) | C1GF—C2GF—C3GF—C4GF | −1.4 (6) |
C2GD—C3GD—C4GD—C5GD | −0.3 (5) | C7GF—C2GF—C3GF—C4GF | −179.8 (4) |
C6GD—C5GD—C4GD—C3GD | 0.7 (5) | C2GF—C3GF—C4GF—C5GF | −1.1 (6) |
C1X—C2X—C3X—C4X | 57.7 (4) | C6GF—C5GF—C4GF—C3GF | 1.7 (6) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1X—H1X···N1GAi | 0.95 (2) | 1.83 (2) | 2.781 (4) | 174 (4) |
O1Y—H1Y···N1GCii | 0.94 (2) | 1.92 (2) | 2.819 (4) | 159 (4) |
O2X—H2X···N1GE | 0.91 (2) | 1.93 (2) | 2.835 (4) | 171 (5) |
O2Y—H2Y···N1GFii | 0.95 (2) | 1.87 (2) | 2.801 (4) | 166 (4) |
N1GA—H1A2···O1Xiii | 0.93 (2) | 2.13 (3) | 3.025 (4) | 161 (3) |
N1GE—H1E2···O2Xiv | 0.94 (2) | 2.24 (3) | 3.115 (4) | 155 (3) |
N1GF—H1F2···O1Yv | 0.93 (2) | 2.24 (2) | 3.147 (4) | 165 (3) |
N1GC—H1C2···O2Yvi | 0.99 (2) | 2.11 (2) | 3.042 (4) | 157 (3) |
Symmetry codes: (i) x−1, y, z; (ii) x−1, y+1, z; (iii) −x+1, −y+1, −z; (iv) −x, −y+2, −z; (v) −x+1/2, y−3/2, −z+1/2; (vi) −x+1/2, y−1/2, −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 = 328.93 | Dx = 1.214 Mg m−3 Dm = N/A Mg m−3 Dm measured by not measured |
Monoclinic, C2/c | Melting point: 412.95K fro guest release onset temp. and 463.15K for host melting K |
a = 18.1704 (10) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 12.2744 (10) Å | µ = 0.08 mm−1 |
c = 16.2036 (10) Å | T = 173 K |
β = 95.30 (3)° | Cuboid, colourless |
V = 3598.5 (4) Å3 | 0.40 × 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 tube | Rint = 0.022 |
Graphite monochromator | θmax = 25.3°, θmin = 3.2° |
1° φ scans and ω scans | h = −21→20 |
9719 measured reflections | k = −14→13 |
3283 independent reflections | l = −19→17 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H 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 reflections | Δρmax = 0.18 e Å−3 |
288 parameters | Δρmin = −0.16 e Å−3 |
13 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.01908 (6) | 0.27005 (8) | 0.17142 (6) | 0.0443 (3) | |
O2 | −0.44209 (6) | 0.57211 (8) | 0.12302 (7) | 0.0485 (3) | |
C7 | −0.14417 (7) | 0.40093 (9) | −0.00027 (7) | 0.0256 (3) | |
C17 | −0.33178 (7) | 0.61808 (10) | 0.06122 (7) | 0.0307 (3) | |
H17 | −0.3329 | 0.6893 | 0.0840 | 0.037* | |
C13 | −0.27099 (6) | 0.48452 (9) | −0.02053 (7) | 0.0248 (3) | |
C9 | −0.10168 (7) | 0.34588 (10) | 0.13998 (7) | 0.0312 (3) | |
H9 | −0.1109 | 0.3390 | 0.1965 | 0.037* | |
C1 | −0.20352 (7) | 0.44860 (10) | −0.06455 (7) | 0.0263 (3) | |
C14 | −0.32842 (7) | 0.41328 (10) | −0.00715 (8) | 0.0306 (3) | |
H14 | −0.3283 | 0.3425 | −0.0308 | 0.037* | |
C8 | −0.15542 (7) | 0.38957 (10) | 0.08290 (7) | 0.0281 (3) | |
H8 | −0.2011 | 0.4123 | 0.1013 | 0.034* | |
C18 | −0.27476 (7) | 0.58791 (10) | 0.01477 (7) | 0.0291 (3) | |
H18 | −0.2370 | 0.6393 | 0.0067 | 0.035* | |
C3 | −0.27854 (8) | 0.40330 (11) | −0.20184 (8) | 0.0378 (3) | |
H31 | −0.2882 | 0.3455 | −0.2440 | 0.045* | |
H32 | −0.3260 | 0.4219 | −0.1798 | 0.045* | |
C10 | −0.03519 (7) | 0.31264 (10) | 0.11470 (7) | 0.0309 (3) | |
C15 | −0.38561 (7) | 0.44196 (11) | 0.03937 (8) | 0.0344 (3) | |
H15 | −0.4238 | 0.3912 | 0.0472 | 0.041* | |
C2 | −0.22454 (7) | 0.36076 (10) | −0.13152 (7) | 0.0297 (3) | |
H21 | −0.1791 | 0.3351 | −0.1547 | 0.036* | |
H22 | −0.2470 | 0.2977 | −0.1052 | 0.036* | |
C6 | −0.17024 (7) | 0.54543 (10) | −0.10976 (8) | 0.0319 (3) | |
H61 | −0.1562 | 0.6038 | −0.0691 | 0.038* | |
H62 | −0.1248 | 0.5210 | −0.1337 | 0.038* | |
C11 | −0.02235 (8) | 0.32228 (12) | 0.03250 (8) | 0.0389 (3) | |
H11 | 0.0234 | 0.2991 | 0.0145 | 0.047* | |
C12 | −0.07633 (7) | 0.36583 (12) | −0.02376 (8) | 0.0364 (3) | |
H12 | −0.0668 | 0.3720 | −0.0802 | 0.044* | |
C16 | −0.38702 (7) | 0.54460 (10) | 0.07446 (7) | 0.0309 (3) | |
C5 | −0.22429 (8) | 0.59133 (11) | −0.17875 (8) | 0.0394 (3) | |
H51 | −0.2683 | 0.6205 | −0.1546 | 0.047* | |
H52 | −0.2005 | 0.6520 | −0.2065 | 0.047* | |
C4 | −0.24813 (9) | 0.50364 (12) | −0.24227 (8) | 0.0431 (4) | |
H41 | −0.2865 | 0.5337 | −0.2833 | 0.052* | |
H42 | −0.2052 | 0.4823 | −0.2721 | 0.052* | |
N1G | −0.04794 (19) | 0.0560 (3) | −0.3235 (2) | 0.0512 (9) | 0.50 |
C1G | −0.0347 (2) | 0.1689 (3) | −0.3024 (3) | 0.0361 (8) | 0.50 |
C5G | −0.0610 (4) | 0.3583 (7) | −0.3267 (5) | 0.0580 (18) | 0.50 |
H5G | −0.0887 | 0.4146 | −0.3553 | 0.070* | 0.50 |
C3G | 0.03287 (19) | 0.3044 (3) | −0.2209 (2) | 0.0458 (8) | 0.50 |
C6G | −0.07526 (17) | 0.2494 (3) | −0.34677 (18) | 0.0464 (7) | 0.50 |
H6G | −0.1120 | 0.2305 | −0.3899 | 0.056* | 0.50 |
C8G | 0.0917 (4) | 0.3359 (7) | −0.1538 (5) | 0.067 (2) | 0.50 |
H8G1 | 0.1406 | 0.3221 | −0.1727 | 0.101* | 0.50 |
H8G2 | 0.0860 | 0.2926 | −0.1040 | 0.101* | 0.50 |
H8G3 | 0.0870 | 0.4134 | −0.1409 | 0.101* | 0.50 |
C2G | 0.0198 (2) | 0.1954 (3) | −0.2403 (3) | 0.0366 (11) | 0.50 |
C4G | −0.0054 (17) | 0.3840 (3) | −0.2638 (11) | 0.064 (5) | 0.50 |
H4G | 0.0056 | 0.4582 | −0.2512 | 0.077* | 0.50 |
C7G | 0.0642 (3) | 0.1069 (5) | −0.1953 (3) | 0.0523 (10) | 0.50 |
H7G1 | 0.1024 | 0.1396 | −0.1564 | 0.078* | 0.50 |
H7G2 | 0.0876 | 0.0619 | −0.2355 | 0.078* | 0.50 |
H7G3 | 0.0316 | 0.0615 | −0.1648 | 0.078* | 0.50 |
H1A | 0.0314 (18) | 0.1990 (16) | 0.153 (2) | 0.063 (10)* | 0.50 |
H1B | 0.008 (3) | 0.270 (3) | 0.2279 (14) | 0.093 (13)* | 0.50 |
H2B | −0.440 (2) | 0.6470 (18) | 0.140 (3) | 0.108 (16)* | 0.50 |
H2A | −0.4782 (16) | 0.515 (3) | 0.134 (2) | 0.082 (12)* | 0.50 |
H1G1 | −0.051 (2) | 0.0214 (19) | −0.2732 (14) | 0.098* | 0.50 |
H1G2 | −0.0889 (17) | 0.057 (2) | −0.3632 (17) | 0.098* | 0.50 |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0501 (6) | 0.0439 (6) | 0.0357 (6) | 0.0174 (5) | −0.0139 (5) | −0.0071 (4) |
O2 | 0.0442 (6) | 0.0413 (6) | 0.0641 (7) | 0.0039 (5) | 0.0266 (5) | −0.0078 (5) |
C7 | 0.0296 (7) | 0.0223 (6) | 0.0248 (6) | −0.0009 (5) | 0.0022 (5) | −0.0024 (5) |
C17 | 0.0392 (8) | 0.0215 (6) | 0.0318 (7) | 0.0030 (6) | 0.0047 (6) | −0.0023 (5) |
C13 | 0.0276 (7) | 0.0235 (6) | 0.0229 (6) | 0.0010 (5) | −0.0002 (5) | 0.0012 (5) |
C9 | 0.0383 (8) | 0.0322 (7) | 0.0235 (6) | 0.0013 (6) | 0.0036 (5) | −0.0023 (5) |
C1 | 0.0299 (7) | 0.0254 (6) | 0.0240 (6) | −0.0004 (5) | 0.0035 (5) | −0.0001 (5) |
C14 | 0.0328 (7) | 0.0235 (7) | 0.0356 (7) | −0.0013 (6) | 0.0037 (5) | −0.0049 (5) |
C8 | 0.0288 (7) | 0.0286 (7) | 0.0273 (6) | 0.0009 (5) | 0.0042 (5) | −0.0030 (5) |
C18 | 0.0342 (7) | 0.0235 (7) | 0.0298 (6) | −0.0022 (6) | 0.0032 (5) | 0.0004 (5) |
C3 | 0.0439 (8) | 0.0421 (8) | 0.0266 (7) | 0.0033 (7) | −0.0021 (6) | −0.0054 (6) |
C10 | 0.0357 (8) | 0.0273 (7) | 0.0285 (7) | 0.0044 (6) | −0.0038 (5) | −0.0057 (5) |
C15 | 0.0299 (7) | 0.0303 (7) | 0.0440 (8) | −0.0042 (6) | 0.0080 (6) | −0.0023 (6) |
C2 | 0.0346 (7) | 0.0285 (7) | 0.0262 (6) | 0.0018 (6) | 0.0042 (5) | −0.0025 (5) |
C6 | 0.0343 (7) | 0.0303 (7) | 0.0320 (7) | −0.0003 (6) | 0.0084 (5) | 0.0017 (5) |
C11 | 0.0323 (7) | 0.0524 (9) | 0.0322 (7) | 0.0122 (7) | 0.0043 (6) | −0.0043 (6) |
C12 | 0.0366 (8) | 0.0483 (8) | 0.0250 (6) | 0.0071 (6) | 0.0064 (5) | −0.0003 (6) |
C16 | 0.0310 (7) | 0.0298 (7) | 0.0325 (7) | 0.0063 (6) | 0.0057 (5) | 0.0006 (5) |
C5 | 0.0490 (9) | 0.0355 (8) | 0.0349 (7) | 0.0053 (7) | 0.0110 (6) | 0.0113 (6) |
C4 | 0.0524 (9) | 0.0496 (9) | 0.0271 (7) | 0.0108 (7) | 0.0026 (6) | 0.0068 (6) |
N1G | 0.0338 (18) | 0.042 (2) | 0.079 (2) | −0.0088 (15) | 0.0115 (15) | −0.0188 (17) |
C1G | 0.027 (2) | 0.030 (2) | 0.053 (2) | −0.0024 (17) | 0.013 (2) | −0.0040 (18) |
C5G | 0.063 (5) | 0.048 (3) | 0.067 (5) | 0.010 (3) | 0.027 (3) | 0.009 (3) |
C3G | 0.054 (2) | 0.044 (2) | 0.0430 (18) | −0.0119 (18) | 0.0225 (14) | −0.0113 (16) |
C6G | 0.0376 (18) | 0.057 (2) | 0.0456 (18) | 0.0044 (16) | 0.0093 (14) | 0.0051 (15) |
C8G | 0.082 (5) | 0.066 (5) | 0.056 (3) | −0.032 (4) | 0.018 (4) | −0.017 (3) |
C2G | 0.029 (3) | 0.0385 (18) | 0.043 (3) | −0.0015 (13) | 0.009 (3) | 0.003 (2) |
C4G | 0.090 (8) | 0.0349 (17) | 0.077 (12) | −0.010 (4) | 0.052 (10) | −0.002 (2) |
C7G | 0.041 (3) | 0.052 (3) | 0.062 (3) | −0.005 (2) | −0.0040 (19) | 0.010 (2) |
Geometric parameters (Å, º) top
O1—C10 | 1.3867 (15) | C2—H22 | 0.9900 |
O1—H1A | 0.955 (14) | C6—C5 | 1.5261 (18) |
O1—H1B | 0.953 (14) | C6—H61 | 0.9900 |
O2—C16 | 1.3710 (16) | C6—H62 | 0.9900 |
O2—H2B | 0.960 (17) | C11—C12 | 1.3833 (18) |
O2—H2A | 0.992 (15) | C11—H11 | 0.9500 |
C7—C8 | 1.3887 (17) | C12—H12 | 0.9500 |
C7—C12 | 1.3916 (18) | C5—C4 | 1.524 (2) |
C7—C1 | 1.5435 (17) | C5—H51 | 0.9900 |
C17—C16 | 1.3810 (18) | C5—H52 | 0.9900 |
C17—C18 | 1.3859 (18) | C4—H41 | 0.9900 |
C17—H17 | 0.9500 | C4—H42 | 0.9900 |
C13—C14 | 1.3936 (17) | N1G—C1G | 1.442 (5) |
C13—C18 | 1.3962 (17) | N1G—H1G1 | 0.926 (17) |
C13—C1 | 1.5388 (17) | N1G—H1G2 | 0.938 (17) |
C9—C10 | 1.3731 (18) | C1G—C2G | 1.383 (7) |
C9—C8 | 1.3891 (17) | C1G—C6G | 1.392 (5) |
C9—H9 | 0.9500 | C5G—C6G | 1.394 (9) |
C1—C6 | 1.5482 (17) | C5G—C4G | 1.40 (3) |
C1—C2 | 1.5523 (16) | C5G—H5G | 0.9500 |
C14—C15 | 1.3844 (18) | C3G—C4G | 1.353 (19) |
C14—H14 | 0.9500 | C3G—C2G | 1.390 (5) |
C8—H8 | 0.9500 | C3G—C8G | 1.504 (8) |
C18—H18 | 0.9500 | C6G—H6G | 0.9500 |
C3—C4 | 1.523 (2) | C8G—H8G1 | 0.9800 |
C3—C2 | 1.5255 (17) | C8G—H8G2 | 0.9800 |
C3—H31 | 0.9900 | C8G—H8G3 | 0.9800 |
C3—H32 | 0.9900 | C2G—C7G | 1.501 (6) |
C10—C11 | 1.3785 (18) | C4G—H4G | 0.9500 |
C15—C16 | 1.3834 (18) | C7G—H7G1 | 0.9800 |
C15—H15 | 0.9500 | C7G—H7G2 | 0.9800 |
C2—H21 | 0.9900 | C7G—H7G3 | 0.9800 |
| | | |
C10—O1—H1A | 108 (2) | H21—C2—H22 | 107.8 |
C10—O1—H1B | 116 (3) | C5—C6—C1 | 112.15 (10) |
H1A—O1—H1B | 112 (3) | C5—C6—H61 | 109.2 |
C16—O2—H2B | 113 (2) | C1—C6—H61 | 109.2 |
C16—O2—H2A | 117 (2) | C5—C6—H62 | 109.2 |
H2B—O2—H2A | 130 (3) | C1—C6—H62 | 109.2 |
C8—C7—C12 | 116.61 (11) | H61—C6—H62 | 107.9 |
C8—C7—C1 | 122.45 (11) | C10—C11—C12 | 119.80 (12) |
C12—C7—C1 | 120.94 (10) | C10—C11—H11 | 120.1 |
C16—C17—C18 | 120.02 (11) | C12—C11—H11 | 120.1 |
C16—C17—H17 | 120.0 | C11—C12—C7 | 122.10 (11) |
C18—C17—H17 | 120.0 | C11—C12—H12 | 118.9 |
C14—C13—C18 | 116.16 (11) | C7—C12—H12 | 118.9 |
C14—C13—C1 | 122.17 (11) | O2—C16—C17 | 120.52 (11) |
C18—C13—C1 | 121.44 (11) | O2—C16—C15 | 120.16 (12) |
C10—C9—C8 | 120.00 (11) | C17—C16—C15 | 119.31 (12) |
C10—C9—H9 | 120.0 | C4—C5—C6 | 110.95 (11) |
C8—C9—H9 | 120.0 | C4—C5—H51 | 109.4 |
C13—C1—C7 | 109.44 (9) | C6—C5—H51 | 109.4 |
C13—C1—C6 | 111.23 (10) | C4—C5—H52 | 109.4 |
C7—C1—C6 | 109.35 (10) | C6—C5—H52 | 109.4 |
C13—C1—C2 | 111.58 (10) | H51—C5—H52 | 108.0 |
C7—C1—C2 | 108.66 (10) | C3—C4—C5 | 111.87 (11) |
C6—C1—C2 | 106.50 (9) | C3—C4—H41 | 109.2 |
C15—C14—C13 | 122.38 (12) | C5—C4—H41 | 109.2 |
C15—C14—H14 | 118.8 | C3—C4—H42 | 109.2 |
C13—C14—H14 | 118.8 | C5—C4—H42 | 109.2 |
C7—C8—C9 | 121.83 (12) | H41—C4—H42 | 107.9 |
C7—C8—H8 | 119.1 | C1G—N1G—H1G1 | 104.8 (17) |
C9—C8—H8 | 119.1 | C1G—N1G—H1G2 | 105.1 (16) |
C17—C18—C13 | 122.19 (12) | H1G1—N1G—H1G2 | 120 (3) |
C17—C18—H18 | 118.9 | C2G—C1G—C6G | 121.2 (4) |
C13—C18—H18 | 118.9 | C2G—C1G—N1G | 119.4 (4) |
C4—C3—C2 | 111.36 (11) | C6G—C1G—N1G | 119.4 (4) |
C4—C3—H31 | 109.4 | C6G—C5G—C4G | 119.4 (8) |
C2—C3—H31 | 109.4 | C6G—C5G—H5G | 120.3 |
C4—C3—H32 | 109.4 | C4G—C5G—H5G | 120.3 |
C2—C3—H32 | 109.4 | C4G—C3G—C2G | 120.7 (9) |
H31—C3—H32 | 108.0 | C4G—C3G—C8G | 118.9 (8) |
C9—C10—C11 | 119.65 (12) | C2G—C3G—C8G | 120.4 (5) |
C9—C10—O1 | 120.38 (11) | C1G—C6G—C5G | 118.8 (4) |
C11—C10—O1 | 119.96 (12) | C1G—C6G—H6G | 120.6 |
C16—C15—C14 | 119.92 (12) | C5G—C6G—H6G | 120.6 |
C16—C15—H15 | 120.0 | C1G—C2G—C3G | 119.1 (4) |
C14—C15—H15 | 120.0 | C1G—C2G—C7G | 120.0 (4) |
C3—C2—C1 | 112.60 (10) | C3G—C2G—C7G | 120.9 (3) |
C3—C2—H21 | 109.1 | C3G—C4G—C5G | 120.8 (7) |
C1—C2—H21 | 109.1 | C3G—C4G—H4G | 119.6 |
C3—C2—H22 | 109.1 | C5G—C4G—H4G | 119.6 |
C1—C2—H22 | 109.1 | | |
| | | |
C14—C13—C1—C7 | −87.60 (13) | C7—C1—C6—C5 | 175.81 (10) |
C18—C13—C1—C7 | 86.60 (13) | C2—C1—C6—C5 | 58.57 (13) |
C14—C13—C1—C6 | 151.47 (11) | C9—C10—C11—C12 | 0.3 (2) |
C18—C13—C1—C6 | −34.33 (14) | O1—C10—C11—C12 | −179.35 (13) |
C14—C13—C1—C2 | 32.69 (15) | C10—C11—C12—C7 | 0.0 (2) |
C18—C13—C1—C2 | −153.11 (10) | C8—C7—C12—C11 | −0.3 (2) |
C8—C7—C1—C13 | 3.01 (15) | C1—C7—C12—C11 | −179.66 (12) |
C12—C7—C1—C13 | −177.72 (11) | C18—C17—C16—O2 | 177.41 (11) |
C8—C7—C1—C6 | 125.07 (12) | C18—C17—C16—C15 | −1.47 (18) |
C12—C7—C1—C6 | −55.65 (15) | C14—C15—C16—O2 | −177.68 (12) |
C8—C7—C1—C2 | −119.06 (12) | C14—C15—C16—C17 | 1.20 (19) |
C12—C7—C1—C2 | 60.22 (15) | C1—C6—C5—C4 | −58.15 (14) |
C18—C13—C14—C15 | −0.92 (18) | C2—C3—C4—C5 | −52.89 (16) |
C1—C13—C14—C15 | 173.56 (11) | C6—C5—C4—C3 | 53.76 (16) |
C12—C7—C8—C9 | 0.28 (18) | C2G—C1G—C6G—C5G | −1.0 (6) |
C1—C7—C8—C9 | 179.59 (11) | N1G—C1G—C6G—C5G | −178.9 (5) |
C10—C9—C8—C7 | 0.08 (19) | C4G—C5G—C6G—C1G | 1.3 (15) |
C16—C17—C18—C13 | 0.53 (18) | C6G—C1G—C2G—C3G | 1.3 (5) |
C14—C13—C18—C17 | 0.65 (17) | N1G—C1G—C2G—C3G | 179.2 (4) |
C1—C13—C18—C17 | −173.88 (11) | C6G—C1G—C2G—C7G | −178.1 (4) |
C8—C9—C10—C11 | −0.39 (19) | N1G—C1G—C2G—C7G | −0.2 (6) |
C8—C9—C10—O1 | 179.29 (11) | C4G—C3G—C2G—C1G | −2.0 (14) |
C13—C14—C15—C16 | 0.02 (19) | C8G—C3G—C2G—C1G | −179.9 (5) |
C4—C3—C2—C1 | 56.33 (14) | C4G—C3G—C2G—C7G | 177.4 (13) |
C13—C1—C2—C3 | 63.86 (13) | C8G—C3G—C2G—C7G | −0.5 (7) |
C7—C1—C2—C3 | −175.39 (10) | C2G—C3G—C4G—C5G | 2 (3) |
C6—C1—C2—C3 | −57.70 (13) | C8G—C3G—C4G—C5G | −179.7 (15) |
C13—C1—C6—C5 | −63.21 (13) | C6G—C5G—C4G—C3G | −2 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···O2i | 0.96 (1) | 1.71 (1) | 2.6680 (14) | 177 (3) |
O1—H1B···O1ii | 0.95 (1) | 1.75 (1) | 2.700 (2) | 176 (5) |
O2—H2A···N1Giii | 0.99 (2) | 1.73 (2) | 2.689 (4) | 162 (3) |
O2—H2B···O1iv | 0.96 (2) | 1.78 (2) | 2.6680 (14) | 153 (3) |
Symmetry codes: (i) x+1/2, y−1/2, z; (ii) −x, y, −z+1/2; (iii) x−1/2, −y+1/2, z+1/2; (iv) x−1/2, 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 = 510.70 | F(000) = 552 |
Triclinic, P1 | Dx = 1.186 Mg m−3 Dm = N/A Mg m−3 Dm measured by not measured |
a = 6.3593 (3) Å | Melting point: 346.55K fro guest release onset temp. and 463.15K for host melting K |
b = 10.8368 (5) Å | Mo Kα radiation, λ = 0.71069 Å |
c = 21.7366 (11) Å | µ = 0.07 mm−1 |
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 tube | Rint = 0.018 |
Graphite monochromator | θmax = 26.3°, θmin = 3.3° |
1° φ scans and ω scans | h = −7→7 |
6145 measured reflections | k = −13→13 |
4517 independent reflections | l = −26→22 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.045 | H 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 reflections | Δρmax = 0.21 e Å−3 |
371 parameters | Δρmin = −0.18 e Å−3 |
10 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | Occ. (<1) |
O1 | 0.5590 (2) | 0.78196 (12) | 0.22041 (6) | 0.0362 (3) | |
O2 | 0.2785 (2) | −0.07316 (12) | 0.23413 (6) | 0.0350 (4) | |
C9 | 0.2727 (3) | 0.64108 (17) | 0.15268 (9) | 0.0291 (4) | |
H9 | 0.1847 | 0.6981 | 0.1575 | 0.035* | |
C1 | 0.2387 (3) | 0.31170 (15) | 0.06770 (8) | 0.0242 (4) | |
C2 | 0.3900 (3) | 0.31687 (16) | 0.01209 (8) | 0.0269 (4) | |
H21 | 0.3952 | 0.3949 | −0.0100 | 0.032* | |
H22 | 0.5411 | 0.3255 | 0.0278 | 0.032* | |
C10 | 0.4753 (3) | 0.67120 (16) | 0.18270 (8) | 0.0271 (4) | |
C12 | 0.5243 (3) | 0.47490 (17) | 0.13756 (9) | 0.0311 (5) | |
H12 | 0.6139 | 0.4188 | 0.1325 | 0.037* | |
C13 | 0.2449 (3) | 0.20332 (15) | 0.10984 (8) | 0.0234 (4) | |
C8 | 0.1967 (3) | 0.52741 (16) | 0.11538 (8) | 0.0270 (4) | |
H8 | 0.0567 | 0.5086 | 0.0948 | 0.032* | |
C7 | 0.3180 (3) | 0.44035 (15) | 0.10712 (8) | 0.0240 (4) | |
C16 | 0.2618 (3) | 0.01733 (16) | 0.19399 (8) | 0.0269 (4) | |
C15 | 0.4211 (3) | 0.05187 (16) | 0.15058 (9) | 0.0291 (4) | |
H15 | 0.5370 | 0.0130 | 0.1489 | 0.035* | |
C17 | 0.0942 (3) | 0.07449 (16) | 0.19541 (8) | 0.0287 (4) | |
H17 | −0.0167 | 0.0511 | 0.2248 | 0.034* | |
C6 | 0.0047 (3) | 0.29067 (16) | 0.03997 (9) | 0.0273 (4) | |
H61 | −0.0989 | 0.2839 | 0.0739 | 0.033* | |
H62 | 0.0021 | 0.3669 | 0.0173 | 0.033* | |
C14 | 0.4112 (3) | 0.14324 (16) | 0.10953 (9) | 0.0277 (4) | |
H14 | 0.5219 | 0.1658 | 0.0801 | 0.033* | |
C5 | −0.0731 (3) | 0.16994 (17) | −0.00361 (9) | 0.0330 (5) | |
H52 | −0.2236 | 0.1611 | −0.0199 | 0.040* | |
H51 | −0.0782 | 0.0928 | 0.0192 | 0.040* | |
C18 | 0.0873 (3) | 0.16597 (16) | 0.15415 (8) | 0.0273 (4) | |
H18 | −0.0289 | 0.2046 | 0.1561 | 0.033* | |
C11 | 0.6028 (3) | 0.58784 (17) | 0.17472 (9) | 0.0326 (5) | |
H11 | 0.7440 | 0.6082 | 0.1948 | 0.039* | |
C3 | 0.3159 (3) | 0.19829 (17) | −0.03357 (9) | 0.0301 (4) | |
H31 | 0.4145 | 0.2104 | −0.0688 | 0.036* | |
H32 | 0.3266 | 0.1210 | −0.0131 | 0.036* | |
C4 | 0.0805 (3) | 0.17675 (18) | −0.05710 (9) | 0.0350 (5) | |
H42 | 0.0319 | 0.0952 | −0.0835 | 0.042* | |
H41 | 0.0736 | 0.2484 | −0.0825 | 0.042* | |
N1GA | 0.9441 (3) | 0.84666 (16) | 0.31320 (8) | 0.0356 (4) | |
C1GA | 0.9539 (3) | 0.95632 (17) | 0.35436 (9) | 0.0298 (5) | |
C2GA | 1.1155 (3) | 0.99578 (17) | 0.40176 (9) | 0.0309 (5) | |
C3GA | 1.1276 (3) | 1.10706 (18) | 0.43950 (9) | 0.0356 (5) | |
C6GA | 0.8077 (3) | 1.02710 (19) | 0.34425 (9) | 0.0364 (5) | |
H6GA | 0.6982 | 0.9997 | 0.3119 | 0.044* | |
C7GA | 1.2707 (3) | 0.9169 (2) | 0.41274 (10) | 0.0426 (5) | |
H7A1 | 1.2059 | 0.8505 | 0.4412 | 0.064* | |
H7A2 | 1.4106 | 0.9735 | 0.4307 | 0.064* | |
H7A3 | 1.2965 | 0.8754 | 0.3735 | 0.064* | |
C5GA | 0.8221 (3) | 1.1376 (2) | 0.38140 (10) | 0.0423 (5) | |
H5GA | 0.7228 | 1.1865 | 0.3745 | 0.051* | |
C4GA | 0.9807 (3) | 1.17706 (19) | 0.42855 (10) | 0.0405 (5) | |
H4GA | 0.9894 | 1.2531 | 0.4539 | 0.049* | |
C8GA | 1.2955 (4) | 1.1506 (2) | 0.49204 (10) | 0.0486 (6) | |
H8A1 | 1.2759 | 1.2277 | 0.5142 | 0.073* | |
H8A2 | 1.4436 | 1.1711 | 0.4758 | 0.073* | |
H8A3 | 1.2764 | 1.0813 | 0.5203 | 0.073* | |
C2GB | 0.8197 (4) | 0.4344 (2) | 0.31847 (10) | 0.0462 (6) | |
C3GB | 0.6093 (4) | 0.3884 (2) | 0.34114 (11) | 0.0478 (6) | |
C1GB | 0.9867 (4) | 0.5202 (2) | 0.35533 (11) | 0.0487 (6) | |
C5GB | 0.7379 (5) | 0.5069 (2) | 0.43806 (12) | 0.0637 (8) | |
H5GB | 0.7113 | 0.5299 | 0.4794 | 0.076* | |
C8GB | 0.4296 (4) | 0.2976 (2) | 0.30512 (12) | 0.0593 (7) | |
H8B1 | 0.2967 | 0.2776 | 0.3292 | 0.089* | 0.50 |
H8B2 | 0.4685 | 0.2180 | 0.2946 | 0.089* | 0.50 |
H8B3 | 0.4023 | 0.3360 | 0.2672 | 0.089* | 0.50 |
H8B4 | 0.4816 | 0.2768 | 0.2648 | 0.089* | 0.50 |
H8B5 | 0.3099 | 0.3364 | 0.2994 | 0.089* | 0.50 |
H8B6 | 0.3760 | 0.2184 | 0.3269 | 0.089* | 0.50 |
C4GB | 0.5705 (4) | 0.4266 (2) | 0.40135 (11) | 0.0542 (6) | |
H6GB | 0.4272 | 0.3967 | 0.4169 | 0.065* | |
N1GB | 1.2056 (5) | 0.5777 (3) | 0.33197 (15) | 0.0827 (8) | |
C6GB | 0.9450 (5) | 0.5546 (2) | 0.41538 (12) | 0.0592 (7) | |
H4GB | 1.0597 | 0.6114 | 0.4410 | 0.071* | |
C7GB | 0.8717 (5) | 0.3866 (3) | 0.25551 (11) | 0.0722 (8) | |
H7B1 | 0.9540 | 0.3238 | 0.2601 | 0.108* | |
H7B2 | 0.9605 | 0.4597 | 0.2340 | 0.108* | |
H7B3 | 0.7344 | 0.3452 | 0.2316 | 0.108* | |
H1A1 | 0.979 (3) | 0.7826 (17) | 0.3352 (10) | 0.056 (7)* | |
H1 | 0.455 (3) | 0.8326 (19) | 0.2250 (11) | 0.062 (7)* | |
H1A2 | 0.806 (3) | 0.816 (2) | 0.2903 (9) | 0.057 (7)* | |
H2 | 0.152 (3) | −0.098 (2) | 0.2607 (11) | 0.087 (9)* | |
H1B1 | 1.327 (6) | 0.618 (4) | 0.3634 (17) | 0.18 (2)* | |
H1B2 | 1.251 (6) | 0.508 (3) | 0.3081 (16) | 0.135 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0357 (8) | 0.0294 (7) | 0.0430 (9) | 0.0117 (6) | −0.0089 (7) | −0.0085 (6) |
O2 | 0.0456 (8) | 0.0354 (7) | 0.0313 (8) | 0.0215 (6) | 0.0064 (7) | 0.0097 (6) |
C9 | 0.0289 (10) | 0.0270 (9) | 0.0345 (11) | 0.0132 (8) | −0.0010 (9) | 0.0011 (9) |
C1 | 0.0217 (9) | 0.0213 (8) | 0.0277 (10) | 0.0037 (7) | −0.0005 (8) | 0.0006 (8) |
C2 | 0.0258 (9) | 0.0247 (9) | 0.0292 (11) | 0.0053 (8) | 0.0004 (8) | 0.0049 (8) |
C10 | 0.0292 (10) | 0.0227 (9) | 0.0275 (11) | 0.0053 (8) | −0.0013 (8) | −0.0005 (8) |
C12 | 0.0284 (10) | 0.0278 (10) | 0.0395 (12) | 0.0130 (8) | −0.0039 (9) | −0.0018 (9) |
C13 | 0.0227 (9) | 0.0218 (8) | 0.0245 (10) | 0.0056 (7) | −0.0020 (8) | −0.0023 (7) |
C8 | 0.0229 (9) | 0.0277 (9) | 0.0301 (11) | 0.0074 (8) | −0.0038 (8) | 0.0006 (8) |
C7 | 0.0229 (9) | 0.0233 (9) | 0.0256 (10) | 0.0059 (8) | 0.0015 (8) | 0.0046 (8) |
C16 | 0.0350 (10) | 0.0231 (9) | 0.0230 (10) | 0.0098 (8) | −0.0011 (8) | 0.0003 (8) |
C15 | 0.0276 (10) | 0.0281 (9) | 0.0332 (11) | 0.0114 (8) | 0.0002 (9) | 0.0002 (8) |
C17 | 0.0330 (10) | 0.0302 (10) | 0.0246 (10) | 0.0117 (8) | 0.0076 (8) | 0.0017 (8) |
C6 | 0.0249 (9) | 0.0251 (9) | 0.0313 (11) | 0.0060 (8) | −0.0015 (8) | 0.0042 (8) |
C14 | 0.0248 (9) | 0.0276 (9) | 0.0300 (11) | 0.0060 (8) | 0.0048 (8) | 0.0042 (8) |
C5 | 0.0261 (10) | 0.0301 (10) | 0.0387 (12) | 0.0029 (8) | −0.0088 (9) | −0.0007 (9) |
C18 | 0.0294 (10) | 0.0290 (9) | 0.0263 (10) | 0.0134 (8) | 0.0023 (8) | −0.0003 (8) |
C11 | 0.0268 (10) | 0.0318 (10) | 0.0387 (12) | 0.0097 (8) | −0.0087 (9) | −0.0031 (9) |
C3 | 0.0319 (10) | 0.0297 (10) | 0.0262 (11) | 0.0052 (8) | 0.0025 (8) | 0.0015 (8) |
C4 | 0.0386 (11) | 0.0321 (10) | 0.0312 (11) | 0.0071 (9) | −0.0056 (9) | −0.0033 (9) |
N1GA | 0.0395 (10) | 0.0344 (9) | 0.0335 (10) | 0.0114 (8) | −0.0018 (9) | 0.0043 (8) |
C1GA | 0.0311 (10) | 0.0325 (10) | 0.0260 (11) | 0.0082 (9) | 0.0058 (9) | 0.0078 (8) |
C2GA | 0.0307 (10) | 0.0330 (10) | 0.0284 (11) | 0.0071 (9) | 0.0030 (9) | 0.0085 (9) |
C3GA | 0.0381 (11) | 0.0352 (11) | 0.0305 (12) | 0.0046 (9) | 0.0058 (9) | 0.0088 (9) |
C6GA | 0.0342 (11) | 0.0453 (12) | 0.0317 (12) | 0.0136 (9) | 0.0019 (9) | 0.0085 (10) |
C7GA | 0.0367 (11) | 0.0459 (12) | 0.0450 (13) | 0.0116 (10) | −0.0023 (10) | 0.0052 (10) |
C5GA | 0.0445 (12) | 0.0455 (12) | 0.0450 (14) | 0.0234 (10) | 0.0085 (11) | 0.0125 (11) |
C4GA | 0.0495 (13) | 0.0355 (11) | 0.0368 (13) | 0.0122 (10) | 0.0081 (11) | 0.0030 (10) |
C8GA | 0.0515 (14) | 0.0495 (13) | 0.0385 (13) | 0.0054 (11) | −0.0041 (11) | 0.0018 (11) |
C2GB | 0.0786 (17) | 0.0407 (12) | 0.0325 (13) | 0.0369 (12) | 0.0049 (12) | 0.0075 (10) |
C3GB | 0.0718 (16) | 0.0379 (12) | 0.0391 (13) | 0.0253 (12) | −0.0058 (12) | 0.0013 (10) |
C1GB | 0.0678 (16) | 0.0347 (11) | 0.0498 (15) | 0.0227 (12) | 0.0110 (13) | 0.0098 (11) |
C5GB | 0.095 (2) | 0.0474 (14) | 0.0395 (14) | 0.0066 (14) | 0.0189 (15) | −0.0055 (12) |
C8GB | 0.0668 (16) | 0.0518 (14) | 0.0579 (17) | 0.0180 (13) | −0.0234 (14) | −0.0035 (13) |
C4GB | 0.0693 (16) | 0.0439 (13) | 0.0461 (15) | 0.0111 (12) | 0.0102 (13) | 0.0023 (11) |
N1GB | 0.0751 (17) | 0.0716 (16) | 0.108 (2) | 0.0284 (14) | 0.0258 (17) | 0.0164 (16) |
C6GB | 0.0830 (18) | 0.0391 (12) | 0.0488 (15) | 0.0092 (13) | −0.0001 (14) | −0.0052 (11) |
C7GB | 0.114 (2) | 0.0894 (19) | 0.0383 (15) | 0.0692 (18) | 0.0037 (15) | 0.0021 (14) |
Geometric parameters (Å, º) top
O1—C10 | 1.375 (2) | N1GA—H1A1 | 0.941 (14) |
O1—H1 | 0.980 (13) | N1GA—H1A2 | 0.958 (13) |
O2—C16 | 1.376 (2) | C1GA—C6GA | 1.388 (3) |
O2—H2 | 0.983 (13) | C1GA—C2GA | 1.397 (3) |
C9—C10 | 1.374 (3) | C2GA—C3GA | 1.399 (3) |
C9—C8 | 1.388 (2) | C2GA—C7GA | 1.506 (3) |
C9—H9 | 0.9500 | C3GA—C4GA | 1.389 (3) |
C1—C7 | 1.537 (2) | C3GA—C8GA | 1.504 (3) |
C1—C13 | 1.541 (2) | C6GA—C5GA | 1.383 (3) |
C1—C6 | 1.544 (2) | C6GA—H6GA | 0.9500 |
C1—C2 | 1.553 (2) | C7GA—H7A1 | 0.9800 |
C2—C3 | 1.528 (2) | C7GA—H7A2 | 0.9800 |
C2—H21 | 0.9900 | C7GA—H7A3 | 0.9800 |
C2—H22 | 0.9900 | C5GA—C4GA | 1.381 (3) |
C10—C11 | 1.384 (2) | C5GA—H5GA | 0.9500 |
C12—C11 | 1.382 (3) | C4GA—H4GA | 0.9500 |
C12—C7 | 1.397 (2) | C8GA—H8A1 | 0.9800 |
C12—H12 | 0.9500 | C8GA—H8A2 | 0.9800 |
C13—C14 | 1.393 (2) | C8GA—H8A3 | 0.9800 |
C13—C18 | 1.394 (2) | C2GB—C1GB | 1.392 (3) |
C8—C7 | 1.388 (2) | C2GB—C3GB | 1.396 (3) |
C8—H8 | 0.9500 | C2GB—C7GB | 1.511 (3) |
C16—C17 | 1.379 (2) | C3GB—C4GB | 1.397 (3) |
C16—C15 | 1.384 (2) | C3GB—C8GB | 1.451 (3) |
C15—C14 | 1.386 (2) | C1GB—C6GB | 1.388 (3) |
C15—H15 | 0.9500 | C1GB—N1GB | 1.464 (3) |
C17—C18 | 1.385 (2) | C5GB—C4GB | 1.368 (4) |
C17—H17 | 0.9500 | C5GB—C6GB | 1.380 (3) |
C6—C5 | 1.520 (3) | C5GB—H5GB | 0.9500 |
C6—H61 | 0.9900 | C8GB—H8B1 | 0.9800 |
C6—H62 | 0.9900 | C8GB—H8B2 | 0.9800 |
C14—H14 | 0.9500 | C8GB—H8B3 | 0.9800 |
C5—C4 | 1.524 (3) | C8GB—H8B4 | 0.9800 |
C5—H52 | 0.9900 | C8GB—H8B5 | 0.9800 |
C5—H51 | 0.9900 | C8GB—H8B6 | 0.9800 |
C18—H18 | 0.9500 | C4GB—H6GB | 0.9500 |
C11—H11 | 0.9500 | N1GB—H1B1 | 1.002 (19) |
C3—C4 | 1.520 (3) | N1GB—H1B2 | 1.007 (18) |
C3—H31 | 0.9900 | C6GB—H4GB | 0.9500 |
C3—H32 | 0.9900 | C7GB—H7B1 | 0.9800 |
C4—H42 | 0.9900 | C7GB—H7B2 | 0.9800 |
C4—H41 | 0.9900 | C7GB—H7B3 | 0.9800 |
N1GA—C1GA | 1.430 (2) | | |
| | | |
C10—O1—H1 | 112.3 (14) | C6GA—C1GA—N1GA | 118.77 (19) |
C16—O2—H2 | 112.5 (15) | C2GA—C1GA—N1GA | 120.56 (17) |
C10—C9—C8 | 120.09 (16) | C1GA—C2GA—C3GA | 119.29 (18) |
C10—C9—H9 | 120.0 | C1GA—C2GA—C7GA | 119.94 (17) |
C8—C9—H9 | 120.0 | C3GA—C2GA—C7GA | 120.75 (19) |
C7—C1—C13 | 107.24 (14) | C4GA—C3GA—C2GA | 119.4 (2) |
C7—C1—C6 | 111.11 (14) | C4GA—C3GA—C8GA | 119.81 (19) |
C13—C1—C6 | 110.99 (13) | C2GA—C3GA—C8GA | 120.82 (19) |
C7—C1—C2 | 109.00 (12) | C5GA—C6GA—C1GA | 119.8 (2) |
C13—C1—C2 | 112.39 (13) | C5GA—C6GA—H6GA | 120.1 |
C6—C1—C2 | 106.13 (14) | C1GA—C6GA—H6GA | 120.1 |
C3—C2—C1 | 113.84 (13) | C2GA—C7GA—H7A1 | 109.5 |
C3—C2—H21 | 108.8 | C2GA—C7GA—H7A2 | 109.5 |
C1—C2—H21 | 108.8 | H7A1—C7GA—H7A2 | 109.5 |
C3—C2—H22 | 108.8 | C2GA—C7GA—H7A3 | 109.5 |
C1—C2—H22 | 108.8 | H7A1—C7GA—H7A3 | 109.5 |
H21—C2—H22 | 107.7 | H7A2—C7GA—H7A3 | 109.5 |
C9—C10—O1 | 122.75 (16) | C4GA—C5GA—C6GA | 120.1 (2) |
C9—C10—C11 | 119.29 (16) | C4GA—C5GA—H5GA | 120.0 |
O1—C10—C11 | 117.96 (16) | C6GA—C5GA—H5GA | 120.0 |
C11—C12—C7 | 122.35 (16) | C5GA—C4GA—C3GA | 120.91 (19) |
C11—C12—H12 | 118.8 | C5GA—C4GA—H4GA | 119.5 |
C7—C12—H12 | 118.8 | C3GA—C4GA—H4GA | 119.5 |
C14—C13—C18 | 115.95 (16) | C3GA—C8GA—H8A1 | 109.5 |
C14—C13—C1 | 123.50 (14) | C3GA—C8GA—H8A2 | 109.5 |
C18—C13—C1 | 120.41 (15) | H8A1—C8GA—H8A2 | 109.5 |
C7—C8—C9 | 122.30 (17) | C3GA—C8GA—H8A3 | 109.5 |
C7—C8—H8 | 118.8 | H8A1—C8GA—H8A3 | 109.5 |
C9—C8—H8 | 118.8 | H8A2—C8GA—H8A3 | 109.5 |
C8—C7—C12 | 116.08 (16) | C1GB—C2GB—C3GB | 119.8 (2) |
C8—C7—C1 | 124.31 (16) | C1GB—C2GB—C7GB | 119.4 (2) |
C12—C7—C1 | 119.61 (15) | C3GB—C2GB—C7GB | 120.7 (2) |
O2—C16—C17 | 122.85 (15) | C2GB—C3GB—C4GB | 119.4 (2) |
O2—C16—C15 | 118.03 (15) | C2GB—C3GB—C8GB | 122.3 (2) |
C17—C16—C15 | 119.12 (16) | C4GB—C3GB—C8GB | 118.3 (2) |
C16—C15—C14 | 119.90 (16) | C6GB—C1GB—C2GB | 119.6 (2) |
C16—C15—H15 | 120.1 | C6GB—C1GB—N1GB | 118.7 (3) |
C14—C15—H15 | 120.1 | C2GB—C1GB—N1GB | 121.6 (2) |
C16—C17—C18 | 120.21 (15) | C4GB—C5GB—C6GB | 120.4 (2) |
C16—C17—H17 | 119.9 | C4GB—C5GB—H5GB | 119.8 |
C18—C17—H17 | 119.9 | C6GB—C5GB—H5GB | 119.8 |
C5—C6—C1 | 112.89 (14) | C3GB—C8GB—H8B1 | 109.5 |
C5—C6—H61 | 109.0 | C3GB—C8GB—H8B2 | 109.5 |
C1—C6—H61 | 109.0 | H8B1—C8GB—H8B2 | 109.5 |
C5—C6—H62 | 109.0 | C3GB—C8GB—H8B3 | 109.5 |
C1—C6—H62 | 109.0 | H8B1—C8GB—H8B3 | 109.5 |
H61—C6—H62 | 107.8 | H8B2—C8GB—H8B3 | 109.5 |
C15—C14—C13 | 122.51 (15) | C3GB—C8GB—H8B4 | 109.5 |
C15—C14—H14 | 118.7 | H8B1—C8GB—H8B4 | 141.1 |
C13—C14—H14 | 118.7 | H8B2—C8GB—H8B4 | 56.3 |
C6—C5—C4 | 110.84 (14) | H8B3—C8GB—H8B4 | 56.3 |
C6—C5—H52 | 109.5 | C3GB—C8GB—H8B5 | 109.5 |
C4—C5—H52 | 109.5 | H8B1—C8GB—H8B5 | 56.3 |
C6—C5—H51 | 109.5 | H8B2—C8GB—H8B5 | 141.1 |
C4—C5—H51 | 109.5 | H8B3—C8GB—H8B5 | 56.3 |
H52—C5—H51 | 108.1 | H8B4—C8GB—H8B5 | 109.5 |
C17—C18—C13 | 122.31 (16) | C3GB—C8GB—H8B6 | 109.5 |
C17—C18—H18 | 118.8 | H8B1—C8GB—H8B6 | 56.3 |
C13—C18—H18 | 118.8 | H8B2—C8GB—H8B6 | 56.3 |
C12—C11—C10 | 119.87 (17) | H8B3—C8GB—H8B6 | 141.1 |
C12—C11—H11 | 120.1 | H8B4—C8GB—H8B6 | 109.5 |
C10—C11—H11 | 120.1 | H8B5—C8GB—H8B6 | 109.5 |
C4—C3—C2 | 111.08 (15) | C5GB—C4GB—C3GB | 120.3 (2) |
C4—C3—H31 | 109.4 | C5GB—C4GB—H6GB | 119.8 |
C2—C3—H31 | 109.4 | C3GB—C4GB—H6GB | 119.8 |
C4—C3—H32 | 109.4 | C1GB—N1GB—H1B1 | 117 (3) |
C2—C3—H32 | 109.4 | C1GB—N1GB—H1B2 | 108 (2) |
H31—C3—H32 | 108.0 | H1B1—N1GB—H1B2 | 106 (3) |
C3—C4—C5 | 110.84 (16) | C5GB—C6GB—C1GB | 120.3 (2) |
C3—C4—H42 | 109.5 | C5GB—C6GB—H4GB | 119.8 |
C5—C4—H42 | 109.5 | C1GB—C6GB—H4GB | 119.8 |
C3—C4—H41 | 109.5 | C2GB—C7GB—H7B1 | 109.5 |
C5—C4—H41 | 109.5 | C2GB—C7GB—H7B2 | 109.5 |
H42—C4—H41 | 108.1 | H7B1—C7GB—H7B2 | 109.5 |
C1GA—N1GA—H1A1 | 109.5 (14) | C2GB—C7GB—H7B3 | 109.5 |
C1GA—N1GA—H1A2 | 112.2 (13) | H7B1—C7GB—H7B3 | 109.5 |
H1A1—N1GA—H1A2 | 113.3 (19) | H7B2—C7GB—H7B3 | 109.5 |
C6GA—C1GA—C2GA | 120.57 (18) | | |
| | | |
C7—C1—C2—C3 | −175.17 (15) | C1—C13—C18—C17 | −176.07 (16) |
C13—C1—C2—C3 | 66.1 (2) | C7—C12—C11—C10 | 0.0 (3) |
C6—C1—C2—C3 | −55.42 (18) | C9—C10—C11—C12 | −0.9 (3) |
C8—C9—C10—O1 | −179.72 (15) | O1—C10—C11—C12 | 179.52 (16) |
C8—C9—C10—C11 | 0.7 (3) | C1—C2—C3—C4 | 55.9 (2) |
C7—C1—C13—C14 | −101.73 (19) | C2—C3—C4—C5 | −53.96 (19) |
C6—C1—C13—C14 | 136.73 (17) | C6—C5—C4—C3 | 55.8 (2) |
C2—C1—C13—C14 | 18.0 (2) | C6GA—C1GA—C2GA—C3GA | 0.6 (2) |
C7—C1—C13—C18 | 73.86 (19) | N1GA—C1GA—C2GA—C3GA | 176.98 (15) |
C6—C1—C13—C18 | −47.7 (2) | C6GA—C1GA—C2GA—C7GA | 179.10 (16) |
C2—C1—C13—C18 | −166.36 (16) | N1GA—C1GA—C2GA—C7GA | −4.5 (2) |
C10—C9—C8—C7 | 0.4 (3) | C1GA—C2GA—C3GA—C4GA | −0.9 (2) |
C9—C8—C7—C12 | −1.3 (2) | C7GA—C2GA—C3GA—C4GA | −179.38 (16) |
C9—C8—C7—C1 | 178.36 (16) | C1GA—C2GA—C3GA—C8GA | 178.37 (17) |
C11—C12—C7—C8 | 1.1 (3) | C7GA—C2GA—C3GA—C8GA | −0.1 (3) |
C11—C12—C7—C1 | −178.56 (16) | C2GA—C1GA—C6GA—C5GA | 0.0 (3) |
C13—C1—C7—C8 | −122.90 (17) | N1GA—C1GA—C6GA—C5GA | −176.45 (15) |
C6—C1—C7—C8 | −1.4 (2) | C1GA—C6GA—C5GA—C4GA | −0.3 (3) |
C2—C1—C7—C8 | 115.18 (18) | C6GA—C5GA—C4GA—C3GA | 0.0 (3) |
C13—C1—C7—C12 | 56.76 (19) | C2GA—C3GA—C4GA—C5GA | 0.6 (3) |
C6—C1—C7—C12 | 178.22 (15) | C8GA—C3GA—C4GA—C5GA | −178.67 (18) |
C2—C1—C7—C12 | −65.2 (2) | C1GB—C2GB—C3GB—C4GB | −1.7 (3) |
O2—C16—C15—C14 | −179.59 (16) | C7GB—C2GB—C3GB—C4GB | 175.0 (2) |
C17—C16—C15—C14 | 0.3 (3) | C1GB—C2GB—C3GB—C8GB | −179.2 (2) |
O2—C16—C17—C18 | 179.38 (17) | C7GB—C2GB—C3GB—C8GB | −2.5 (3) |
C15—C16—C17—C18 | −0.5 (3) | C3GB—C2GB—C1GB—C6GB | 3.0 (3) |
C7—C1—C6—C5 | 175.28 (14) | C7GB—C2GB—C1GB—C6GB | −173.8 (2) |
C13—C1—C6—C5 | −65.47 (18) | C3GB—C2GB—C1GB—N1GB | −175.7 (2) |
C2—C1—C6—C5 | 56.92 (17) | C7GB—C2GB—C1GB—N1GB | 7.5 (3) |
C16—C15—C14—C13 | 0.0 (3) | C6GB—C5GB—C4GB—C3GB | 2.3 (4) |
C18—C13—C14—C15 | −0.1 (3) | C2GB—C3GB—C4GB—C5GB | −1.0 (3) |
C1—C13—C14—C15 | 175.71 (16) | C8GB—C3GB—C4GB—C5GB | 176.7 (2) |
C1—C6—C5—C4 | −59.3 (2) | C4GB—C5GB—C6GB—C1GB | −1.0 (4) |
C16—C17—C18—C13 | 0.4 (3) | C2GB—C1GB—C6GB—C5GB | −1.7 (4) |
C14—C13—C18—C17 | −0.1 (3) | N1GB—C1GB—C6GB—C5GB | 177.1 (2) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.98 (1) | 1.73 (1) | 2.7071 (17) | 178 (2) |
O2—H2···N1GAii | 0.98 (1) | 1.76 (1) | 2.7341 (19) | 172 (2) |
N1GA—H1A2···O1 | 0.96 (1) | 2.10 (1) | 3.033 (2) | 163 (2) |
N1GA—H1A1···N1GB | 0.94 (1) | 2.98 (1) | 3.789 (3) | 146 (2) |
Symmetry codes: (i) x, y+1, z; (ii) x−1, y−1, z. |
(dc34x0.5) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 3,4-xylidine, water
top
Crystal data top
C18H20O2/0.5(C8H11N)/H2O | Z = 4 |
Mr = 346.95 | F(000) = 748 |
Triclinic, P1 | Dx = 1.230 Mg m−3 Dm = N/A Mg m−3 Dm measured by not measured |
a = 10.8979 (5) Å | Melting point: 359.35K, 392.75K and 403.35K for guests release onset temp. and
463.15K for host melting K |
b = 12.5017 (7) Å | Mo Kα radiation, λ = 0.71069 Å |
c = 15.1701 (7) Å | µ = 0.08 mm−1 |
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 tube | Rint = 0.022 |
Graphite monochromator | θmax = 25.4°, θmin = 2.6° |
1° φ scans and ω scans | h = −13→11 |
10118 measured reflections | k = −11→15 |
6720 independent reflections | l = −18→15 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.065 | H 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 reflections | Δρmax = 0.38 e Å−3 |
497 parameters | Δρmin = −0.36 e Å−3 |
22 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1Y | 1.1341 (2) | 0.1345 (2) | 0.17979 (15) | 0.0331 (6) | |
O2Y | 0.2774 (2) | −0.01417 (19) | 0.13813 (14) | 0.0324 (6) | |
O1X | 0.2661 (2) | 0.47495 (19) | 0.14053 (14) | 0.0338 (6) | |
C1Y | 0.7649 (3) | 0.0817 (2) | 0.40287 (19) | 0.0187 (7) | |
C1X | 0.7598 (3) | 0.5796 (2) | 0.39954 (19) | 0.0179 (6) | |
C13Y | 0.6303 (3) | 0.0577 (2) | 0.33582 (18) | 0.0179 (7) | |
C7X | 0.6247 (3) | 0.5543 (2) | 0.33376 (18) | 0.0182 (7) | |
C8X | 0.5668 (3) | 0.4450 (2) | 0.26438 (19) | 0.0216 (7) | |
H8X | 0.6104 | 0.3865 | 0.2607 | 0.026* | |
C10X | 0.3837 (3) | 0.5035 (3) | 0.20438 (19) | 0.0221 (7) | |
C11X | 0.4390 (3) | 0.6137 (3) | 0.2710 (2) | 0.0247 (7) | |
H11X | 0.3961 | 0.6726 | 0.2730 | 0.030* | |
C10Y | 1.0443 (3) | 0.1216 (3) | 0.2325 (2) | 0.0227 (7) | |
C17Y | 0.4481 (3) | 0.1202 (3) | 0.27271 (19) | 0.0226 (7) | |
H17Y | 0.4059 | 0.1795 | 0.2753 | 0.027* | |
C9X | 0.4482 (3) | 0.4188 (3) | 0.20090 (19) | 0.0244 (7) | |
H9X | 0.4111 | 0.3432 | 0.1552 | 0.029* | |
C6Y | 0.8004 (3) | 0.1951 (2) | 0.48859 (19) | 0.0211 (7) | |
H6Y2 | 0.8918 | 0.2116 | 0.5233 | 0.025* | |
H6Y1 | 0.7942 | 0.2601 | 0.4647 | 0.025* | |
C8Y | 0.9482 (3) | 0.0229 (2) | 0.32947 (19) | 0.0214 (7) | |
H8Y | 0.9445 | −0.0356 | 0.3582 | 0.026* | |
C17X | 1.0334 (3) | 0.5357 (3) | 0.2726 (2) | 0.0251 (7) | |
H17X | 1.0898 | 0.4874 | 0.2652 | 0.030* | |
C14X | 0.8680 (3) | 0.6740 (2) | 0.2944 (2) | 0.0230 (7) | |
H14X | 0.8109 | 0.7218 | 0.3009 | 0.028* | |
C7Y | 0.8652 (3) | 0.0929 (2) | 0.34328 (18) | 0.0176 (6) | |
C9Y | 1.0365 (3) | 0.0365 (3) | 0.2746 (2) | 0.0259 (7) | |
H9Y | 1.0917 | −0.0128 | 0.2660 | 0.031* | |
C16Y | 0.3936 (3) | 0.0114 (3) | 0.20444 (19) | 0.0226 (7) | |
C16X | 1.0389 (3) | 0.6192 (3) | 0.2290 (2) | 0.0221 (7) | |
C15Y | 0.4564 (3) | −0.0741 (3) | 0.20081 (19) | 0.0231 (7) | |
H15Y | 0.4196 | −0.1489 | 0.1538 | 0.028* | |
C14Y | 0.5723 (3) | −0.0506 (2) | 0.26543 (19) | 0.0209 (7) | |
H14Y | 0.6143 | −0.1103 | 0.2620 | 0.025* | |
C5Y | 0.7143 (3) | 0.1911 (3) | 0.5579 (2) | 0.0246 (7) | |
H5Y1 | 0.7464 | 0.2644 | 0.6127 | 0.029* | |
H5Y2 | 0.6245 | 0.1849 | 0.5259 | 0.029* | |
C12Y | 0.8748 (3) | 0.1774 (3) | 0.29940 (19) | 0.0229 (7) | |
H12Y | 0.8190 | 0.2263 | 0.3071 | 0.028* | |
C2Y | 0.7673 (3) | −0.0178 (2) | 0.44374 (19) | 0.0209 (7) | |
H2Y1 | 0.7411 | −0.0926 | 0.3907 | 0.025* | |
H2Y2 | 0.8572 | −0.0063 | 0.4789 | 0.025* | |
C18X | 0.9448 (3) | 0.5227 (3) | 0.3276 (2) | 0.0241 (7) | |
H18X | 0.9422 | 0.4654 | 0.3575 | 0.029* | |
C2X | 0.7653 (3) | 0.4819 (2) | 0.44222 (19) | 0.0215 (7) | |
H2X1 | 0.7401 | 0.4065 | 0.3900 | 0.026* | |
H2X2 | 0.8557 | 0.4953 | 0.4775 | 0.026* | |
C3X | 0.6761 (3) | 0.4754 (3) | 0.5091 (2) | 0.0254 (7) | |
H3X2 | 0.5851 | 0.4583 | 0.4734 | 0.031* | |
H3X1 | 0.6826 | 0.4111 | 0.5340 | 0.031* | |
C12X | 0.5578 (3) | 0.6376 (3) | 0.3348 (2) | 0.0223 (7) | |
H12X | 0.5945 | 0.7132 | 0.3806 | 0.027* | |
C6X | 0.7956 (3) | 0.6937 (2) | 0.48495 (19) | 0.0209 (7) | |
H6X1 | 0.8872 | 0.7105 | 0.5195 | 0.025* | |
H6X2 | 0.7888 | 0.7583 | 0.4607 | 0.025* | |
C13X | 0.8599 (3) | 0.5912 (2) | 0.33983 (19) | 0.0190 (7) | |
C11Y | 0.9629 (3) | 0.1927 (3) | 0.2449 (2) | 0.0228 (7) | |
H11Y | 0.9674 | 0.2515 | 0.2163 | 0.027* | |
C3Y | 0.6771 (3) | −0.0248 (3) | 0.5104 (2) | 0.0268 (7) | |
H3Y2 | 0.5863 | −0.0415 | 0.4746 | 0.032* | |
H3Y1 | 0.6832 | −0.0892 | 0.5351 | 0.032* | |
C18Y | 0.5650 (3) | 0.1422 (2) | 0.33750 (19) | 0.0204 (7) | |
H18Y | 0.6016 | 0.2170 | 0.3844 | 0.024* | |
C15X | 0.9562 (3) | 0.6892 (3) | 0.2403 (2) | 0.0248 (7) | |
H15X | 0.9599 | 0.7473 | 0.2110 | 0.030* | |
C5X | 0.7098 (3) | 0.6897 (3) | 0.55464 (19) | 0.0236 (7) | |
H5X2 | 0.7408 | 0.7637 | 0.6087 | 0.028* | |
H5X1 | 0.6195 | 0.6816 | 0.5225 | 0.028* | |
C4X | 0.7120 (3) | 0.5888 (3) | 0.5916 (2) | 0.0266 (7) | |
H4X1 | 0.7998 | 0.6021 | 0.6312 | 0.032* | |
H4X2 | 0.6497 | 0.5839 | 0.6317 | 0.032* | |
C4Y | 0.7135 (3) | 0.0889 (3) | 0.5931 (2) | 0.0303 (8) | |
H4Y2 | 0.6505 | 0.0843 | 0.6327 | 0.036* | |
H4Y1 | 0.8006 | 0.1010 | 0.6332 | 0.036* | |
C4G | 0.6040 (4) | 0.3300 (3) | 0.0191 (3) | 0.0491 (11) | |
C2G | 0.4564 (4) | 0.1540 (3) | 0.0175 (3) | 0.0491 (11) | |
H2G | 0.4403 | 0.0874 | 0.0368 | 0.059* | |
N1G | 0.2260 (3) | 0.0939 (3) | −0.0650 (2) | 0.0654 (10) | |
C3G | 0.5808 (4) | 0.2316 (3) | 0.0484 (2) | 0.0442 (10) | |
C5G | 0.5015 (5) | 0.3446 (3) | −0.0394 (3) | 0.0544 (11) | |
H5G | 0.5177 | 0.4105 | −0.0597 | 0.065* | |
C6G | 0.3767 (5) | 0.2697 (3) | −0.0707 (3) | 0.0594 (13) | |
H6G | 0.3087 | 0.2834 | −0.1104 | 0.071* | |
C1G | 0.3564 (4) | 0.1720 (3) | −0.0404 (3) | 0.0459 (10) | |
C7G | 0.6829 (4) | 0.2078 (4) | 0.1057 (3) | 0.0627 (12) | |
H7G1 | 0.6463 | 0.1435 | 0.1269 | 0.094* | |
H7G2 | 0.7283 | 0.2773 | 0.1611 | 0.094* | |
H7G3 | 0.7443 | 0.1864 | 0.0684 | 0.094* | |
C8G | 0.7396 (4) | 0.4149 (3) | 0.0554 (3) | 0.0689 (14) | |
H8G1 | 0.7422 | 0.4783 | 0.0292 | 0.103* | |
H8G2 | 0.8027 | 0.3741 | 0.0354 | 0.103* | |
H8G3 | 0.7611 | 0.4468 | 0.1248 | 0.103* | |
O2X | 1.1278 (2) | 0.6313 (2) | 0.17562 (15) | 0.0331 (6) | |
O2W | 0.1109 (2) | 0.2480 (2) | 0.05724 (18) | 0.0510 (7) | |
O1W | 0.1062 (2) | 0.7659 (3) | 0.0720 (2) | 0.0710 (10) | |
H1X | 0.226 (3) | 0.539 (2) | 0.154 (3) | 0.069 (13)* | |
H2Y | 0.229 (4) | 0.042 (3) | 0.153 (3) | 0.103 (17)* | |
H1Y | 1.122 (4) | 0.186 (3) | 0.143 (2) | 0.091 (15)* | |
H2X | 1.113 (4) | 0.676 (3) | 0.135 (3) | 0.089 (15)* | |
H1W2 | 0.033 (3) | 0.758 (4) | 0.025 (3) | 0.107* | |
H2W1 | 0.155 (4) | 0.328 (2) | 0.097 (3) | 0.107* | |
H1G1 | 0.202 (3) | 0.063 (3) | −0.1348 (17) | 0.107* | |
H1G2 | 0.257 (3) | 0.032 (3) | −0.042 (3) | 0.107* | |
H2W2 | 0.160 (4) | 0.203 (3) | 0.020 (3) | 0.107* | |
H1W1 | 0.165 (4) | 0.840 (2) | 0.090 (3) | 0.107* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1Y | 0.0298 (12) | 0.0462 (15) | 0.0425 (14) | 0.0216 (11) | 0.0224 (11) | 0.0274 (12) |
O2Y | 0.0238 (12) | 0.0381 (15) | 0.0266 (12) | 0.0111 (11) | −0.0059 (9) | 0.0034 (10) |
O1X | 0.0292 (13) | 0.0374 (15) | 0.0296 (12) | 0.0181 (11) | −0.0037 (10) | 0.0032 (11) |
C1Y | 0.0200 (15) | 0.0168 (16) | 0.0203 (15) | 0.0054 (13) | 0.0040 (12) | 0.0081 (13) |
C1X | 0.0183 (15) | 0.0151 (16) | 0.0212 (15) | 0.0052 (12) | 0.0052 (12) | 0.0067 (13) |
C13Y | 0.0177 (15) | 0.0202 (17) | 0.0180 (15) | 0.0054 (13) | 0.0078 (12) | 0.0078 (13) |
C7X | 0.0190 (15) | 0.0195 (17) | 0.0181 (15) | 0.0064 (13) | 0.0053 (12) | 0.0083 (13) |
C8X | 0.0243 (16) | 0.0185 (17) | 0.0238 (16) | 0.0114 (13) | 0.0067 (13) | 0.0055 (13) |
C10X | 0.0172 (16) | 0.0319 (19) | 0.0179 (16) | 0.0096 (14) | 0.0031 (12) | 0.0081 (14) |
C11X | 0.0262 (17) | 0.0255 (19) | 0.0269 (17) | 0.0151 (14) | 0.0060 (13) | 0.0099 (14) |
C10Y | 0.0161 (16) | 0.0269 (19) | 0.0251 (17) | 0.0050 (14) | 0.0055 (13) | 0.0090 (14) |
C17Y | 0.0255 (17) | 0.0233 (18) | 0.0239 (16) | 0.0142 (14) | 0.0077 (13) | 0.0090 (14) |
C9X | 0.0242 (17) | 0.0246 (18) | 0.0209 (16) | 0.0081 (14) | 0.0027 (13) | 0.0032 (14) |
C6Y | 0.0221 (16) | 0.0176 (17) | 0.0218 (16) | 0.0041 (13) | 0.0023 (12) | 0.0069 (13) |
C8Y | 0.0235 (16) | 0.0206 (17) | 0.0230 (16) | 0.0087 (13) | 0.0049 (13) | 0.0104 (13) |
C17X | 0.0231 (17) | 0.0263 (19) | 0.0325 (18) | 0.0153 (14) | 0.0089 (14) | 0.0122 (15) |
C14X | 0.0219 (16) | 0.0204 (17) | 0.0319 (17) | 0.0112 (13) | 0.0087 (13) | 0.0114 (14) |
C7Y | 0.0156 (15) | 0.0171 (16) | 0.0187 (15) | 0.0054 (12) | 0.0013 (12) | 0.0049 (13) |
C9Y | 0.0253 (17) | 0.0286 (19) | 0.0310 (18) | 0.0152 (14) | 0.0092 (14) | 0.0139 (15) |
C16Y | 0.0197 (16) | 0.0310 (19) | 0.0175 (15) | 0.0090 (14) | 0.0037 (12) | 0.0079 (14) |
C16X | 0.0172 (16) | 0.0250 (18) | 0.0264 (17) | 0.0066 (14) | 0.0073 (13) | 0.0105 (14) |
C15Y | 0.0280 (17) | 0.0193 (17) | 0.0191 (16) | 0.0090 (14) | 0.0072 (13) | −0.0005 (13) |
C14Y | 0.0217 (16) | 0.0193 (17) | 0.0226 (16) | 0.0111 (13) | 0.0049 (13) | 0.0048 (13) |
C5Y | 0.0256 (17) | 0.0242 (18) | 0.0210 (16) | 0.0069 (14) | 0.0036 (13) | 0.0047 (14) |
C12Y | 0.0218 (16) | 0.0218 (18) | 0.0285 (17) | 0.0099 (13) | 0.0081 (13) | 0.0095 (14) |
C2Y | 0.0224 (16) | 0.0169 (17) | 0.0260 (16) | 0.0081 (13) | 0.0048 (13) | 0.0101 (13) |
C18X | 0.0221 (16) | 0.0254 (18) | 0.0303 (17) | 0.0093 (14) | 0.0076 (13) | 0.0153 (15) |
C2X | 0.0217 (16) | 0.0204 (17) | 0.0223 (16) | 0.0070 (13) | 0.0019 (12) | 0.0080 (13) |
C3X | 0.0290 (17) | 0.0223 (18) | 0.0299 (17) | 0.0074 (14) | 0.0095 (14) | 0.0147 (14) |
C12X | 0.0239 (16) | 0.0175 (17) | 0.0246 (16) | 0.0068 (13) | 0.0068 (13) | 0.0047 (13) |
C6X | 0.0196 (15) | 0.0186 (17) | 0.0238 (16) | 0.0045 (13) | 0.0040 (12) | 0.0074 (13) |
C13X | 0.0167 (15) | 0.0179 (17) | 0.0197 (15) | 0.0020 (13) | 0.0025 (12) | 0.0057 (13) |
C11Y | 0.0232 (16) | 0.0231 (18) | 0.0269 (17) | 0.0089 (14) | 0.0070 (13) | 0.0132 (14) |
C3Y | 0.0293 (18) | 0.0265 (19) | 0.0335 (18) | 0.0118 (15) | 0.0112 (14) | 0.0184 (15) |
C18Y | 0.0241 (16) | 0.0143 (16) | 0.0224 (16) | 0.0067 (13) | 0.0039 (13) | 0.0056 (13) |
C15X | 0.0277 (17) | 0.0201 (18) | 0.0318 (17) | 0.0085 (14) | 0.0107 (14) | 0.0132 (14) |
C5X | 0.0272 (17) | 0.0221 (18) | 0.0200 (16) | 0.0080 (14) | 0.0059 (13) | 0.0041 (13) |
C4X | 0.0290 (17) | 0.031 (2) | 0.0238 (16) | 0.0098 (15) | 0.0079 (13) | 0.0136 (15) |
C4Y | 0.0351 (19) | 0.036 (2) | 0.0275 (17) | 0.0144 (16) | 0.0116 (14) | 0.0159 (16) |
C4G | 0.081 (3) | 0.0201 (19) | 0.043 (2) | 0.0025 (19) | 0.047 (2) | −0.0039 (17) |
C2G | 0.072 (3) | 0.022 (2) | 0.051 (2) | 0.0010 (19) | 0.046 (2) | −0.0004 (17) |
N1G | 0.059 (2) | 0.050 (2) | 0.059 (2) | −0.0064 (18) | 0.0147 (18) | −0.0070 (18) |
C3G | 0.063 (3) | 0.044 (2) | 0.034 (2) | 0.027 (2) | 0.0290 (18) | 0.0068 (17) |
C5G | 0.100 (4) | 0.031 (2) | 0.047 (2) | 0.027 (2) | 0.042 (2) | 0.0139 (18) |
C6G | 0.095 (3) | 0.021 (2) | 0.059 (3) | 0.003 (2) | 0.057 (2) | −0.0049 (18) |
C1G | 0.051 (2) | 0.039 (2) | 0.039 (2) | 0.0127 (19) | 0.0185 (18) | −0.0047 (17) |
C7G | 0.066 (3) | 0.076 (3) | 0.053 (3) | 0.032 (2) | 0.020 (2) | 0.019 (2) |
C8G | 0.086 (3) | 0.045 (3) | 0.047 (2) | −0.021 (2) | 0.040 (2) | −0.0107 (19) |
O2X | 0.0328 (13) | 0.0424 (15) | 0.0436 (14) | 0.0201 (11) | 0.0228 (11) | 0.0287 (12) |
O2W | 0.0360 (15) | 0.0557 (18) | 0.0597 (18) | 0.0026 (13) | 0.0003 (12) | 0.0316 (14) |
O1W | 0.0412 (17) | 0.064 (2) | 0.100 (2) | −0.0128 (14) | −0.0166 (15) | 0.0573 (19) |
Geometric parameters (Å, º) top
O1Y—C10Y | 1.376 (3) | C12Y—H12Y | 0.9500 |
O1Y—H1Y | 0.977 (15) | C2Y—C3Y | 1.533 (4) |
O2Y—C16Y | 1.387 (3) | C2Y—H2Y1 | 0.9900 |
O2Y—H2Y | 0.964 (14) | C2Y—H2Y2 | 0.9900 |
O1X—C10X | 1.374 (3) | C18X—C13X | 1.392 (4) |
O1X—H1X | 0.984 (14) | C18X—H18X | 0.9500 |
C1Y—C7Y | 1.542 (4) | C2X—C3X | 1.527 (4) |
C1Y—C2Y | 1.543 (4) | C2X—H2X1 | 0.9900 |
C1Y—C6Y | 1.547 (4) | C2X—H2X2 | 0.9900 |
C1Y—C13Y | 1.548 (4) | C3X—C4X | 1.520 (4) |
C1X—C13X | 1.541 (4) | C3X—H3X2 | 0.9900 |
C1X—C7X | 1.542 (4) | C3X—H3X1 | 0.9900 |
C1X—C2X | 1.544 (4) | C12X—H12X | 0.9500 |
C1X—C6X | 1.549 (4) | C6X—C5X | 1.531 (4) |
C13Y—C18Y | 1.393 (4) | C6X—H6X1 | 0.9900 |
C13Y—C14Y | 1.395 (4) | C6X—H6X2 | 0.9900 |
C7X—C12X | 1.393 (4) | C11Y—H11Y | 0.9500 |
C7X—C8X | 1.397 (4) | C3Y—C4Y | 1.524 (4) |
C8X—C9X | 1.383 (4) | C3Y—H3Y2 | 0.9900 |
C8X—H8X | 0.9500 | C3Y—H3Y1 | 0.9900 |
C10X—C11X | 1.386 (4) | C18Y—H18Y | 0.9500 |
C10X—C9X | 1.386 (4) | C15X—H15X | 0.9500 |
C11X—C12X | 1.393 (4) | C5X—C4X | 1.522 (4) |
C11X—H11X | 0.9500 | C5X—H5X2 | 0.9900 |
C10Y—C9Y | 1.383 (4) | C5X—H5X1 | 0.9900 |
C10Y—C11Y | 1.385 (4) | C4X—H4X1 | 0.9900 |
C17Y—C16Y | 1.383 (4) | C4X—H4X2 | 0.9900 |
C17Y—C18Y | 1.389 (4) | C4Y—H4Y2 | 0.9900 |
C17Y—H17Y | 0.9500 | C4Y—H4Y1 | 0.9900 |
C9X—H9X | 0.9500 | C4G—C5G | 1.382 (6) |
C6Y—C5Y | 1.529 (4) | C4G—C3G | 1.411 (5) |
C6Y—H6Y2 | 0.9900 | C4G—C8G | 1.522 (5) |
C6Y—H6Y1 | 0.9900 | C2G—C1G | 1.378 (5) |
C8Y—C9Y | 1.390 (4) | C2G—C3G | 1.397 (5) |
C8Y—C7Y | 1.391 (4) | C2G—H2G | 0.9500 |
C8Y—H8Y | 0.9500 | N1G—C1G | 1.456 (5) |
C17X—C16X | 1.381 (4) | N1G—H1G1 | 0.98 (2) |
C17X—C18X | 1.393 (4) | N1G—H1G2 | 1.03 (2) |
C17X—H17X | 0.9500 | C3G—C7G | 1.429 (5) |
C14X—C15X | 1.384 (4) | C5G—C6G | 1.387 (6) |
C14X—C13X | 1.393 (4) | C5G—H5G | 0.9500 |
C14X—H14X | 0.9500 | C6G—C1G | 1.410 (5) |
C7Y—C12Y | 1.394 (4) | C6G—H6G | 0.9500 |
C9Y—H9Y | 0.9500 | C7G—H7G1 | 0.9800 |
C16Y—C15Y | 1.382 (4) | C7G—H7G2 | 0.9800 |
C16X—O2X | 1.376 (3) | C7G—H7G3 | 0.9800 |
C16X—C15X | 1.386 (4) | C8G—H8G1 | 0.9800 |
C15Y—C14Y | 1.375 (4) | C8G—H8G2 | 0.9800 |
C15Y—H15Y | 0.9500 | C8G—H8G3 | 0.9800 |
C14Y—H14Y | 0.9500 | O2X—H2X | 0.959 (14) |
C5Y—C4Y | 1.517 (4) | O2W—H2W1 | 0.971 (19) |
C5Y—H5Y1 | 0.9900 | O2W—H2W2 | 0.98 (2) |
C5Y—H5Y2 | 0.9900 | O1W—H1W2 | 0.94 (2) |
C12Y—C11Y | 1.387 (4) | O1W—H1W1 | 0.94 (2) |
| | | |
C10Y—O1Y—H1Y | 113 (2) | C1X—C2X—H2X1 | 109.1 |
C16Y—O2Y—H2Y | 115 (3) | C3X—C2X—H2X2 | 109.1 |
C10X—O1X—H1X | 111 (2) | C1X—C2X—H2X2 | 109.1 |
C7Y—C1Y—C2Y | 111.4 (2) | H2X1—C2X—H2X2 | 107.8 |
C7Y—C1Y—C6Y | 108.9 (2) | C4X—C3X—C2X | 111.2 (2) |
C2Y—C1Y—C6Y | 106.8 (2) | C4X—C3X—H3X2 | 109.4 |
C7Y—C1Y—C13Y | 106.6 (2) | C2X—C3X—H3X2 | 109.4 |
C2Y—C1Y—C13Y | 110.5 (2) | C4X—C3X—H3X1 | 109.4 |
C6Y—C1Y—C13Y | 112.7 (2) | C2X—C3X—H3X1 | 109.4 |
C13X—C1X—C7X | 107.3 (2) | H3X2—C3X—H3X1 | 108.0 |
C13X—C1X—C2X | 111.3 (2) | C11X—C12X—C7X | 122.2 (3) |
C7X—C1X—C2X | 110.9 (2) | C11X—C12X—H12X | 118.9 |
C13X—C1X—C6X | 108.6 (2) | C7X—C12X—H12X | 118.9 |
C7X—C1X—C6X | 112.7 (2) | C5X—C6X—C1X | 113.8 (2) |
C2X—C1X—C6X | 106.1 (2) | C5X—C6X—H6X1 | 108.8 |
C18Y—C13Y—C14Y | 116.6 (2) | C1X—C6X—H6X1 | 108.8 |
C18Y—C13Y—C1Y | 123.2 (2) | C5X—C6X—H6X2 | 108.8 |
C14Y—C13Y—C1Y | 120.2 (2) | C1X—C6X—H6X2 | 108.8 |
C12X—C7X—C8X | 116.4 (2) | H6X1—C6X—H6X2 | 107.7 |
C12X—C7X—C1X | 123.5 (2) | C18X—C13X—C14X | 116.6 (3) |
C8X—C7X—C1X | 119.9 (2) | C18X—C13X—C1X | 123.8 (2) |
C9X—C8X—C7X | 122.5 (3) | C14X—C13X—C1X | 119.6 (3) |
C9X—C8X—H8X | 118.8 | C10Y—C11Y—C12Y | 119.4 (3) |
C7X—C8X—H8X | 118.8 | C10Y—C11Y—H11Y | 120.3 |
O1X—C10X—C11X | 121.9 (3) | C12Y—C11Y—H11Y | 120.3 |
O1X—C10X—C9X | 118.3 (3) | C4Y—C3Y—C2Y | 110.9 (2) |
C11X—C10X—C9X | 119.7 (3) | C4Y—C3Y—H3Y2 | 109.5 |
C10X—C11X—C12X | 119.6 (3) | C2Y—C3Y—H3Y2 | 109.5 |
C10X—C11X—H11X | 120.2 | C4Y—C3Y—H3Y1 | 109.5 |
C12X—C11X—H11X | 120.2 | C2Y—C3Y—H3Y1 | 109.5 |
O1Y—C10Y—C9Y | 119.1 (3) | H3Y2—C3Y—H3Y1 | 108.1 |
O1Y—C10Y—C11Y | 121.4 (3) | C17Y—C18Y—C13Y | 122.0 (3) |
C9Y—C10Y—C11Y | 119.5 (3) | C17Y—C18Y—H18Y | 119.0 |
C16Y—C17Y—C18Y | 119.6 (3) | C13Y—C18Y—H18Y | 119.0 |
C16Y—C17Y—H17Y | 120.2 | C14X—C15X—C16X | 119.6 (3) |
C18Y—C17Y—H17Y | 120.2 | C14X—C15X—H15X | 120.2 |
C8X—C9X—C10X | 119.6 (3) | C16X—C15X—H15X | 120.2 |
C8X—C9X—H9X | 120.2 | C4X—C5X—C6X | 111.4 (2) |
C10X—C9X—H9X | 120.2 | C4X—C5X—H5X2 | 109.4 |
C5Y—C6Y—C1Y | 114.0 (2) | C6X—C5X—H5X2 | 109.4 |
C5Y—C6Y—H6Y2 | 108.8 | C4X—C5X—H5X1 | 109.4 |
C1Y—C6Y—H6Y2 | 108.8 | C6X—C5X—H5X1 | 109.4 |
C5Y—C6Y—H6Y1 | 108.8 | H5X2—C5X—H5X1 | 108.0 |
C1Y—C6Y—H6Y1 | 108.8 | C3X—C4X—C5X | 110.2 (2) |
H6Y2—C6Y—H6Y1 | 107.7 | C3X—C4X—H4X1 | 109.6 |
C9Y—C8Y—C7Y | 121.6 (3) | C5X—C4X—H4X1 | 109.6 |
C9Y—C8Y—H8Y | 119.2 | C3X—C4X—H4X2 | 109.6 |
C7Y—C8Y—H8Y | 119.2 | C5X—C4X—H4X2 | 109.6 |
C16X—C17X—C18X | 119.7 (3) | H4X1—C4X—H4X2 | 108.1 |
C16X—C17X—H17X | 120.1 | C5Y—C4Y—C3Y | 111.1 (2) |
C18X—C17X—H17X | 120.1 | C5Y—C4Y—H4Y2 | 109.4 |
C15X—C14X—C13X | 122.4 (3) | C3Y—C4Y—H4Y2 | 109.4 |
C15X—C14X—H14X | 118.8 | C5Y—C4Y—H4Y1 | 109.4 |
C13X—C14X—H14X | 118.8 | C3Y—C4Y—H4Y1 | 109.4 |
C8Y—C7Y—C12Y | 116.7 (3) | H4Y2—C4Y—H4Y1 | 108.0 |
C8Y—C7Y—C1Y | 124.0 (2) | C5G—C4G—C3G | 117.9 (4) |
C12Y—C7Y—C1Y | 119.2 (3) | C5G—C4G—C8G | 124.0 (4) |
C10Y—C9Y—C8Y | 120.3 (3) | C3G—C4G—C8G | 118.1 (4) |
C10Y—C9Y—H9Y | 119.9 | C1G—C2G—C3G | 121.4 (4) |
C8Y—C9Y—H9Y | 119.9 | C1G—C2G—H2G | 119.3 |
C15Y—C16Y—C17Y | 119.8 (3) | C3G—C2G—H2G | 119.3 |
C15Y—C16Y—O2Y | 118.7 (3) | C1G—N1G—H1G1 | 105 (2) |
C17Y—C16Y—O2Y | 121.5 (3) | C1G—N1G—H1G2 | 94.1 (19) |
O2X—C16X—C17X | 118.9 (3) | H1G1—N1G—H1G2 | 107 (3) |
O2X—C16X—C15X | 121.4 (3) | C2G—C3G—C4G | 119.0 (4) |
C17X—C16X—C15X | 119.7 (3) | C2G—C3G—C7G | 119.7 (4) |
C14Y—C15Y—C16Y | 119.8 (3) | C4G—C3G—C7G | 121.3 (4) |
C14Y—C15Y—H15Y | 120.1 | C4G—C5G—C6G | 124.5 (4) |
C16Y—C15Y—H15Y | 120.1 | C4G—C5G—H5G | 117.8 |
C15Y—C14Y—C13Y | 122.3 (3) | C6G—C5G—H5G | 117.8 |
C15Y—C14Y—H14Y | 118.8 | C5G—C6G—C1G | 116.3 (4) |
C13Y—C14Y—H14Y | 118.8 | C5G—C6G—H6G | 121.8 |
C4Y—C5Y—C6Y | 111.5 (2) | C1G—C6G—H6G | 121.8 |
C4Y—C5Y—H5Y1 | 109.3 | C2G—C1G—C6G | 120.9 (4) |
C6Y—C5Y—H5Y1 | 109.3 | C2G—C1G—N1G | 119.6 (4) |
C4Y—C5Y—H5Y2 | 109.3 | C6G—C1G—N1G | 119.4 (4) |
C6Y—C5Y—H5Y2 | 109.3 | C3G—C7G—H7G1 | 109.5 |
H5Y1—C5Y—H5Y2 | 108.0 | C3G—C7G—H7G2 | 109.5 |
C11Y—C12Y—C7Y | 122.5 (3) | H7G1—C7G—H7G2 | 109.5 |
C11Y—C12Y—H12Y | 118.8 | C3G—C7G—H7G3 | 109.5 |
C7Y—C12Y—H12Y | 118.8 | H7G1—C7G—H7G3 | 109.5 |
C3Y—C2Y—C1Y | 112.8 (2) | H7G2—C7G—H7G3 | 109.5 |
C3Y—C2Y—H2Y1 | 109.0 | C4G—C8G—H8G1 | 109.5 |
C1Y—C2Y—H2Y1 | 109.0 | C4G—C8G—H8G2 | 109.5 |
C3Y—C2Y—H2Y2 | 109.0 | H8G1—C8G—H8G2 | 109.5 |
C1Y—C2Y—H2Y2 | 109.0 | C4G—C8G—H8G3 | 109.5 |
H2Y1—C2Y—H2Y2 | 107.8 | H8G1—C8G—H8G3 | 109.5 |
C13X—C18X—C17X | 121.9 (3) | H8G2—C8G—H8G3 | 109.5 |
C13X—C18X—H18X | 119.0 | C16X—O2X—H2X | 115 (3) |
C17X—C18X—H18X | 119.0 | H2W1—O2W—H2W2 | 118 (3) |
C3X—C2X—C1X | 112.6 (2) | H1W2—O1W—H1W1 | 110 (4) |
C3X—C2X—H2X1 | 109.1 | | |
| | | |
C7Y—C1Y—C13Y—C18Y | −103.1 (3) | C13X—C1X—C2X—C3X | 174.8 (2) |
C2Y—C1Y—C13Y—C18Y | 135.7 (3) | C7X—C1X—C2X—C3X | −65.8 (3) |
C6Y—C1Y—C13Y—C18Y | 16.3 (4) | C6X—C1X—C2X—C3X | 56.9 (3) |
C7Y—C1Y—C13Y—C14Y | 72.7 (3) | C1X—C2X—C3X—C4X | −59.6 (3) |
C2Y—C1Y—C13Y—C14Y | −48.5 (3) | C10X—C11X—C12X—C7X | 0.6 (4) |
C6Y—C1Y—C13Y—C14Y | −167.9 (2) | C8X—C7X—C12X—C11X | 0.5 (4) |
C13X—C1X—C7X—C12X | −102.8 (3) | C1X—C7X—C12X—C11X | 176.4 (3) |
C2X—C1X—C7X—C12X | 135.5 (3) | C13X—C1X—C6X—C5X | −175.3 (2) |
C6X—C1X—C7X—C12X | 16.7 (4) | C7X—C1X—C6X—C5X | 66.0 (3) |
C13X—C1X—C7X—C8X | 73.0 (3) | C2X—C1X—C6X—C5X | −55.6 (3) |
C2X—C1X—C7X—C8X | −48.8 (3) | C17X—C18X—C13X—C14X | −0.1 (4) |
C6X—C1X—C7X—C8X | −167.5 (2) | C17X—C18X—C13X—C1X | 179.7 (3) |
C12X—C7X—C8X—C9X | −1.3 (4) | C15X—C14X—C13X—C18X | −0.5 (4) |
C1X—C7X—C8X—C9X | −177.3 (3) | C15X—C14X—C13X—C1X | 179.6 (3) |
O1X—C10X—C11X—C12X | 179.2 (3) | C7X—C1X—C13X—C18X | −122.3 (3) |
C9X—C10X—C11X—C12X | −1.1 (4) | C2X—C1X—C13X—C18X | −0.7 (4) |
C7X—C8X—C9X—C10X | 0.8 (4) | C6X—C1X—C13X—C18X | 115.7 (3) |
O1X—C10X—C9X—C8X | −179.9 (3) | C7X—C1X—C13X—C14X | 57.6 (3) |
C11X—C10X—C9X—C8X | 0.4 (4) | C2X—C1X—C13X—C14X | 179.1 (2) |
C7Y—C1Y—C6Y—C5Y | −175.3 (2) | C6X—C1X—C13X—C14X | −64.5 (3) |
C2Y—C1Y—C6Y—C5Y | −54.9 (3) | O1Y—C10Y—C11Y—C12Y | −179.3 (3) |
C13Y—C1Y—C6Y—C5Y | 66.6 (3) | C9Y—C10Y—C11Y—C12Y | 0.0 (4) |
C9Y—C8Y—C7Y—C12Y | 0.0 (4) | C7Y—C12Y—C11Y—C10Y | 0.4 (4) |
C9Y—C8Y—C7Y—C1Y | 179.7 (3) | C1Y—C2Y—C3Y—C4Y | −58.4 (3) |
C2Y—C1Y—C7Y—C8Y | −0.8 (4) | C16Y—C17Y—C18Y—C13Y | 0.3 (4) |
C6Y—C1Y—C7Y—C8Y | 116.7 (3) | C14Y—C13Y—C18Y—C17Y | 0.1 (4) |
C13Y—C1Y—C7Y—C8Y | −121.4 (3) | C1Y—C13Y—C18Y—C17Y | 176.0 (2) |
C2Y—C1Y—C7Y—C12Y | 178.9 (2) | C13X—C14X—C15X—C16X | 0.9 (4) |
C6Y—C1Y—C7Y—C12Y | −63.6 (3) | O2X—C16X—C15X—C14X | 179.9 (3) |
C13Y—C1Y—C7Y—C12Y | 58.3 (3) | C17X—C16X—C15X—C14X | −0.6 (4) |
O1Y—C10Y—C9Y—C8Y | 178.9 (3) | C1X—C6X—C5X—C4X | 56.3 (3) |
C11Y—C10Y—C9Y—C8Y | −0.4 (4) | C2X—C3X—C4X—C5X | 55.9 (3) |
C7Y—C8Y—C9Y—C10Y | 0.4 (4) | C6X—C5X—C4X—C3X | −54.1 (3) |
C18Y—C17Y—C16Y—C15Y | −0.5 (4) | C6Y—C5Y—C4Y—C3Y | −53.6 (3) |
C18Y—C17Y—C16Y—O2Y | −179.7 (3) | C2Y—C3Y—C4Y—C5Y | 55.2 (3) |
C18X—C17X—C16X—O2X | 179.5 (3) | C1G—C2G—C3G—C4G | −0.2 (5) |
C18X—C17X—C16X—C15X | 0.0 (4) | C1G—C2G—C3G—C7G | −177.9 (3) |
C17Y—C16Y—C15Y—C14Y | 0.4 (4) | C5G—C4G—C3G—C2G | −0.3 (5) |
O2Y—C16Y—C15Y—C14Y | 179.6 (3) | C8G—C4G—C3G—C2G | 178.7 (3) |
C16Y—C15Y—C14Y—C13Y | 0.0 (4) | C5G—C4G—C3G—C7G | 177.4 (3) |
C18Y—C13Y—C14Y—C15Y | −0.2 (4) | C8G—C4G—C3G—C7G | −3.7 (5) |
C1Y—C13Y—C14Y—C15Y | −176.3 (3) | C3G—C4G—C5G—C6G | 0.8 (5) |
C1Y—C6Y—C5Y—C4Y | 55.3 (3) | C8G—C4G—C5G—C6G | −178.1 (3) |
C8Y—C7Y—C12Y—C11Y | −0.4 (4) | C4G—C5G—C6G—C1G | −0.8 (5) |
C1Y—C7Y—C12Y—C11Y | 179.9 (2) | C3G—C2G—C1G—C6G | 0.2 (5) |
C7Y—C1Y—C2Y—C3Y | 175.1 (2) | C3G—C2G—C1G—N1G | −175.4 (3) |
C6Y—C1Y—C2Y—C3Y | 56.2 (3) | C5G—C6G—C1G—C2G | 0.3 (5) |
C13Y—C1Y—C2Y—C3Y | −66.6 (3) | C5G—C6G—C1G—N1G | 175.8 (3) |
C16X—C17X—C18X—C13X | 0.4 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1Y—H1Y···O2Wi | 0.98 (2) | 1.70 (2) | 2.651 (3) | 165 (4) |
O2Y—H2Y···O1Yii | 0.96 (1) | 1.73 (1) | 2.688 (3) | 176 (4) |
O1X—H1X···O2Xii | 0.98 (1) | 1.74 (1) | 2.709 (3) | 168 (3) |
O2X—H2X···O1Wi | 0.96 (1) | 1.67 (1) | 2.628 (3) | 172 (4) |
O1W—H1W1···O2Yiii | 0.94 (2) | 1.82 (2) | 2.757 (3) | 173 (4) |
O1W—H1W2···O2Wiv | 0.94 (2) | 1.80 (2) | 2.740 (3) | 175 (4) |
O2W—H2W1···O1X | 0.97 (2) | 1.83 (2) | 2.765 (3) | 161 (4) |
O2W—H2W2···N1G | 0.98 (2) | 1.95 (2) | 2.923 (4) | 170 (4) |
Symmetry codes: (i) x+1, y, z; (ii) x−1, 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/C8H11N | F(000) = 1680 |
Mr = 389.52 | Dx = 1.195 Mg m−3 Dm = N/A Mg m−3 Dm measured by not measured |
Monoclinic, C2/c | Melting point: 463.15K for host melting K |
a = 34.965 (1) Å | Mo Kα radiation, λ = 0.71069 Å |
b = 6.2546 (3) Å | µ = 0.07 mm−1 |
c = 20.2035 (8) Å | T = 173 K |
β = 101.577 (1)° | Prism, colourless |
V = 4328.5 (3) Å3 | 0.35 × 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 tube | Rint = 0.111 |
Graphite monochromator | θmax = 28.2°, θmin = 2.1° |
0.8° φ scans and ω scans | h = −43→44 |
7707 measured reflections | k = −4→8 |
4699 independent reflections | l = −25→25 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.104 | H 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 reflections | Δρmax = 0.39 e Å−3 |
278 parameters | Δρmin = −0.30 e Å−3 |
7 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O1 | 0.14735 (8) | 0.8158 (5) | 0.23403 (15) | 0.0367 (8) | |
O2 | 0.15232 (9) | 0.7995 (5) | 0.67500 (15) | 0.0381 (8) | |
C10 | 0.12232 (11) | 0.7839 (8) | 0.27792 (19) | 0.0316 (10) | |
C7 | 0.07230 (11) | 0.7045 (7) | 0.36777 (19) | 0.0276 (9) | |
C1 | 0.04713 (11) | 0.6605 (8) | 0.4214 (2) | 0.0328 (10) | |
C16 | 0.12690 (11) | 0.7581 (7) | 0.6146 (2) | 0.0301 (9) | |
C8 | 0.07383 (12) | 0.9032 (8) | 0.3386 (2) | 0.0363 (10) | |
H8 | 0.0576 | 1.0141 | 0.3495 | 0.044* | |
C13 | 0.07420 (12) | 0.6939 (8) | 0.4911 (2) | 0.0341 (10) | |
C9 | 0.09848 (11) | 0.9472 (8) | 0.2936 (2) | 0.0348 (10) | |
H9 | 0.0989 | 1.0852 | 0.2741 | 0.042* | |
C11 | 0.12138 (12) | 0.5870 (8) | 0.3058 (2) | 0.0348 (10) | |
H11 | 0.1377 | 0.4764 | 0.2949 | 0.042* | |
C2 | 0.01159 (12) | 0.8115 (8) | 0.4126 (2) | 0.0391 (11) | |
H21 | −0.0017 | 0.7904 | 0.4510 | 0.047* | |
H22 | 0.0209 | 0.9613 | 0.4142 | 0.047* | |
C12 | 0.09666 (11) | 0.5464 (8) | 0.3504 (2) | 0.0356 (10) | |
H12 | 0.0963 | 0.4076 | 0.3694 | 0.043* | |
C14 | 0.07464 (13) | 0.8809 (8) | 0.5272 (2) | 0.0429 (12) | |
H14 | 0.0566 | 0.9906 | 0.5100 | 0.052* | |
C6 | 0.03078 (12) | 0.4296 (8) | 0.4153 (2) | 0.0357 (11) | |
H61 | 0.0527 | 0.3276 | 0.4186 | 0.043* | |
H62 | 0.0177 | 0.4013 | 0.4536 | 0.043* | |
C18 | 0.10088 (13) | 0.5367 (8) | 0.5197 (2) | 0.0438 (12) | |
H18 | 0.1013 | 0.4042 | 0.4969 | 0.053* | |
C15 | 0.10086 (14) | 0.9141 (8) | 0.5881 (2) | 0.0459 (12) | |
H15 | 0.1006 | 1.0459 | 0.6114 | 0.055* | |
C5 | 0.00156 (12) | 0.3908 (8) | 0.3486 (2) | 0.0430 (12) | |
H51 | 0.0151 | 0.4081 | 0.3103 | 0.052* | |
H52 | −0.0083 | 0.2422 | 0.3478 | 0.052* | |
C17 | 0.12681 (13) | 0.5688 (8) | 0.5805 (2) | 0.0427 (12) | |
H17 | 0.1446 | 0.4588 | 0.5986 | 0.051* | |
C4 | −0.03273 (13) | 0.5446 (9) | 0.3398 (3) | 0.0514 (14) | |
H41 | −0.0484 | 0.5153 | 0.3746 | 0.062* | |
H42 | −0.0497 | 0.5236 | 0.2948 | 0.062* | |
C3 | −0.01792 (13) | 0.7764 (9) | 0.3466 (2) | 0.0469 (13) | |
H31 | −0.0055 | 0.8111 | 0.3080 | 0.056* | |
H32 | −0.0403 | 0.8742 | 0.3451 | 0.056* | |
N1G | 0.20885 (10) | 0.5013 (6) | 0.21900 (17) | 0.0334 (9) | |
C1G | 0.23266 (11) | 0.6072 (7) | 0.1789 (2) | 0.0307 (9) | |
C2G | 0.21866 (12) | 0.7873 (7) | 0.1411 (2) | 0.0317 (9) | |
H2G | 0.1936 | 0.8416 | 0.1433 | 0.038* | |
C6G | 0.26906 (12) | 0.5285 (8) | 0.1753 (2) | 0.0402 (11) | |
H6G | 0.2791 | 0.4056 | 0.2005 | 0.048* | |
C3G | 0.24074 (12) | 0.8892 (8) | 0.1001 (2) | 0.0364 (11) | |
C7G | 0.22368 (15) | 1.0811 (8) | 0.0591 (2) | 0.0482 (13) | |
H7G1 | 0.2217 | 1.0510 | 0.0110 | 0.072* | |
H7G2 | 0.2406 | 1.2053 | 0.0720 | 0.072* | |
H7G3 | 0.1977 | 1.1114 | 0.0679 | 0.072* | |
C4G | 0.27737 (12) | 0.8099 (8) | 0.0966 (2) | 0.0379 (11) | |
C8G | 0.30226 (14) | 0.9151 (10) | 0.0524 (2) | 0.0529 (14) | |
H8G1 | 0.2885 | 0.9103 | 0.0051 | 0.079* | |
H8G2 | 0.3271 | 0.8386 | 0.0572 | 0.079* | |
H8G3 | 0.3073 | 1.0642 | 0.0663 | 0.079* | |
C5G | 0.29082 (12) | 0.6317 (9) | 0.1342 (2) | 0.0434 (12) | |
H5G | 0.3159 | 0.5770 | 0.1319 | 0.052* | |
H1G2 | 0.2258 | 0.4287 | 0.2651 | 0.12 (3)* | |
H1G1 | 0.1893 (9) | 0.597 (5) | 0.231 (2) | 0.023 (10)* | |
H1 | 0.1479 (12) | 0.961 (4) | 0.219 (2) | 0.033 (12)* | |
H2 | 0.1723 (11) | 0.692 (6) | 0.687 (2) | 0.053 (15)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O1 | 0.0334 (16) | 0.050 (2) | 0.0305 (16) | −0.0030 (15) | 0.0161 (13) | 0.0017 (15) |
O2 | 0.0387 (17) | 0.0494 (19) | 0.0237 (15) | 0.0124 (15) | 0.0001 (13) | −0.0060 (15) |
C10 | 0.0227 (19) | 0.056 (3) | 0.0156 (18) | −0.0036 (19) | 0.0029 (15) | −0.0027 (19) |
C7 | 0.0267 (19) | 0.039 (2) | 0.0165 (18) | 0.0043 (18) | 0.0034 (15) | 0.0046 (18) |
C1 | 0.027 (2) | 0.051 (3) | 0.022 (2) | 0.0071 (19) | 0.0083 (16) | 0.006 (2) |
C16 | 0.028 (2) | 0.043 (2) | 0.0191 (19) | 0.0051 (19) | 0.0045 (15) | 0.0005 (18) |
C8 | 0.032 (2) | 0.053 (3) | 0.025 (2) | 0.007 (2) | 0.0102 (17) | 0.005 (2) |
C13 | 0.029 (2) | 0.055 (3) | 0.021 (2) | 0.011 (2) | 0.0099 (16) | 0.006 (2) |
C9 | 0.032 (2) | 0.049 (3) | 0.024 (2) | 0.000 (2) | 0.0069 (17) | 0.004 (2) |
C11 | 0.031 (2) | 0.049 (3) | 0.026 (2) | 0.006 (2) | 0.0085 (17) | 0.008 (2) |
C2 | 0.033 (2) | 0.060 (3) | 0.028 (2) | 0.016 (2) | 0.0136 (18) | 0.017 (2) |
C12 | 0.030 (2) | 0.052 (3) | 0.026 (2) | 0.009 (2) | 0.0089 (17) | 0.010 (2) |
C14 | 0.047 (3) | 0.051 (3) | 0.028 (2) | 0.021 (2) | 0.001 (2) | 0.005 (2) |
C6 | 0.029 (2) | 0.056 (3) | 0.023 (2) | 0.005 (2) | 0.0098 (17) | 0.012 (2) |
C18 | 0.046 (3) | 0.050 (3) | 0.032 (2) | 0.017 (2) | −0.002 (2) | −0.002 (2) |
C15 | 0.052 (3) | 0.051 (3) | 0.032 (3) | 0.018 (2) | 0.002 (2) | −0.006 (2) |
C5 | 0.034 (2) | 0.062 (3) | 0.032 (2) | 0.005 (2) | 0.0038 (19) | 0.018 (2) |
C17 | 0.043 (3) | 0.050 (3) | 0.032 (2) | 0.017 (2) | −0.0017 (19) | 0.004 (2) |
C4 | 0.029 (2) | 0.086 (4) | 0.037 (3) | 0.003 (3) | 0.001 (2) | 0.020 (3) |
C3 | 0.028 (2) | 0.080 (4) | 0.033 (2) | 0.013 (2) | 0.0057 (19) | 0.014 (3) |
N1G | 0.0311 (18) | 0.046 (2) | 0.0230 (18) | −0.0030 (17) | 0.0039 (14) | 0.0043 (17) |
C1G | 0.028 (2) | 0.044 (2) | 0.0176 (19) | −0.0031 (19) | 0.0006 (15) | −0.0036 (18) |
C2G | 0.030 (2) | 0.043 (2) | 0.0206 (19) | −0.0017 (19) | 0.0017 (16) | 0.0001 (19) |
C6G | 0.034 (2) | 0.055 (3) | 0.029 (2) | 0.002 (2) | 0.0000 (18) | 0.004 (2) |
C3G | 0.036 (2) | 0.054 (3) | 0.017 (2) | −0.006 (2) | 0.0032 (17) | −0.004 (2) |
C7G | 0.059 (3) | 0.056 (3) | 0.032 (3) | 0.001 (3) | 0.013 (2) | 0.011 (2) |
C4G | 0.031 (2) | 0.062 (3) | 0.019 (2) | −0.012 (2) | 0.0016 (16) | −0.009 (2) |
C8G | 0.043 (3) | 0.085 (4) | 0.033 (3) | −0.019 (3) | 0.011 (2) | −0.002 (3) |
C5G | 0.027 (2) | 0.070 (3) | 0.031 (2) | 0.003 (2) | 0.0023 (18) | −0.002 (2) |
Geometric parameters (Å, º) top
O1—C10 | 1.379 (4) | C18—H18 | 0.9500 |
O1—H1 | 0.95 (2) | C15—H15 | 0.9500 |
O2—C16 | 1.383 (5) | C5—C4 | 1.519 (6) |
O2—H2 | 0.97 (2) | C5—H51 | 0.9900 |
C10—C11 | 1.358 (6) | C5—H52 | 0.9900 |
C10—C9 | 1.394 (6) | C17—H17 | 0.9500 |
C7—C8 | 1.381 (6) | C4—C3 | 1.536 (8) |
C7—C12 | 1.396 (6) | C4—H41 | 0.9900 |
C7—C1 | 1.551 (5) | C4—H42 | 0.9900 |
C1—C2 | 1.542 (6) | C3—H31 | 0.9900 |
C1—C13 | 1.546 (6) | C3—H32 | 0.9900 |
C1—C6 | 1.549 (6) | N1G—C1G | 1.434 (5) |
C16—C15 | 1.368 (6) | N1G—H1G2 | 1.0958 |
C16—C17 | 1.369 (6) | N1G—H1G1 | 0.976 (19) |
C8—C9 | 1.401 (5) | C1G—C6G | 1.380 (6) |
C8—H8 | 0.9500 | C1G—C2G | 1.393 (6) |
C13—C14 | 1.377 (6) | C2G—C3G | 1.394 (6) |
C13—C18 | 1.398 (6) | C2G—H2G | 0.9500 |
C9—H9 | 0.9500 | C6G—C5G | 1.393 (6) |
C11—C12 | 1.390 (5) | C6G—H6G | 0.9500 |
C11—H11 | 0.9500 | C3G—C4G | 1.389 (6) |
C2—C3 | 1.530 (6) | C3G—C7G | 1.511 (6) |
C2—H21 | 0.9900 | C7G—H7G1 | 0.9800 |
C2—H22 | 0.9900 | C7G—H7G2 | 0.9800 |
C12—H12 | 0.9500 | C7G—H7G3 | 0.9800 |
C14—C15 | 1.395 (6) | C4G—C5G | 1.377 (7) |
C14—H14 | 0.9500 | C4G—C8G | 1.516 (6) |
C6—C5 | 1.539 (6) | C8G—H8G1 | 0.9800 |
C6—H61 | 0.9900 | C8G—H8G2 | 0.9800 |
C6—H62 | 0.9900 | C8G—H8G3 | 0.9800 |
C18—C17 | 1.386 (6) | C5G—H5G | 0.9500 |
| | | |
C10—O1—H1 | 113 (2) | C4—C5—H51 | 109.3 |
C16—O2—H2 | 113 (3) | C6—C5—H51 | 109.3 |
C11—C10—O1 | 118.0 (4) | C4—C5—H52 | 109.3 |
C11—C10—C9 | 120.3 (4) | C6—C5—H52 | 109.3 |
O1—C10—C9 | 121.6 (4) | H51—C5—H52 | 107.9 |
C8—C7—C12 | 116.9 (4) | C16—C17—C18 | 120.4 (4) |
C8—C7—C1 | 122.2 (4) | C16—C17—H17 | 119.8 |
C12—C7—C1 | 120.7 (4) | C18—C17—H17 | 119.8 |
C2—C1—C13 | 110.7 (4) | C5—C4—C3 | 110.1 (4) |
C2—C1—C6 | 106.6 (3) | C5—C4—H41 | 109.6 |
C13—C1—C6 | 110.3 (4) | C3—C4—H41 | 109.6 |
C2—C1—C7 | 111.6 (3) | C5—C4—H42 | 109.6 |
C13—C1—C7 | 106.4 (3) | C3—C4—H42 | 109.6 |
C6—C1—C7 | 111.3 (3) | H41—C4—H42 | 108.2 |
C15—C16—C17 | 119.1 (4) | C2—C3—C4 | 111.7 (4) |
C15—C16—O2 | 118.1 (4) | C2—C3—H31 | 109.3 |
C17—C16—O2 | 122.8 (4) | C4—C3—H31 | 109.3 |
C7—C8—C9 | 122.4 (4) | C2—C3—H32 | 109.3 |
C7—C8—H8 | 118.8 | C4—C3—H32 | 109.3 |
C9—C8—H8 | 118.8 | H31—C3—H32 | 107.9 |
C14—C13—C18 | 116.3 (4) | C1G—N1G—H1G2 | 113.3 |
C14—C13—C1 | 122.5 (4) | C1G—N1G—H1G1 | 112 (2) |
C18—C13—C1 | 121.2 (4) | H1G2—N1G—H1G1 | 108.8 |
C10—C9—C8 | 118.5 (4) | C6G—C1G—C2G | 119.0 (4) |
C10—C9—H9 | 120.7 | C6G—C1G—N1G | 120.7 (4) |
C8—C9—H9 | 120.7 | C2G—C1G—N1G | 120.2 (4) |
C10—C11—C12 | 120.3 (4) | C1G—C2G—C3G | 121.3 (4) |
C10—C11—H11 | 119.8 | C1G—C2G—H2G | 119.3 |
C12—C11—H11 | 119.8 | C3G—C2G—H2G | 119.3 |
C3—C2—C1 | 113.5 (4) | C1G—C6G—C5G | 119.1 (4) |
C3—C2—H21 | 108.9 | C1G—C6G—H6G | 120.4 |
C1—C2—H21 | 108.9 | C5G—C6G—H6G | 120.4 |
C3—C2—H22 | 108.9 | C4G—C3G—C2G | 119.6 (4) |
C1—C2—H22 | 108.9 | C4G—C3G—C7G | 121.5 (4) |
H21—C2—H22 | 107.7 | C2G—C3G—C7G | 118.9 (4) |
C11—C12—C7 | 121.6 (4) | C3G—C7G—H7G1 | 109.5 |
C11—C12—H12 | 119.2 | C3G—C7G—H7G2 | 109.5 |
C7—C12—H12 | 119.2 | H7G1—C7G—H7G2 | 109.5 |
C13—C14—C15 | 121.9 (4) | C3G—C7G—H7G3 | 109.5 |
C13—C14—H14 | 119.0 | H7G1—C7G—H7G3 | 109.5 |
C15—C14—H14 | 119.0 | H7G2—C7G—H7G3 | 109.5 |
C5—C6—C1 | 112.7 (4) | C5G—C4G—C3G | 118.5 (4) |
C5—C6—H61 | 109.1 | C5G—C4G—C8G | 120.2 (4) |
C1—C6—H61 | 109.1 | C3G—C4G—C8G | 121.3 (5) |
C5—C6—H62 | 109.1 | C4G—C8G—H8G1 | 109.5 |
C1—C6—H62 | 109.1 | C4G—C8G—H8G2 | 109.5 |
H61—C6—H62 | 107.8 | H8G1—C8G—H8G2 | 109.5 |
C17—C18—C13 | 121.9 (5) | C4G—C8G—H8G3 | 109.5 |
C17—C18—H18 | 119.1 | H8G1—C8G—H8G3 | 109.5 |
C13—C18—H18 | 119.1 | H8G2—C8G—H8G3 | 109.5 |
C16—C15—C14 | 120.4 (5) | C4G—C5G—C6G | 122.5 (4) |
C16—C15—H15 | 119.8 | C4G—C5G—H5G | 118.8 |
C14—C15—H15 | 119.8 | C6G—C5G—H5G | 118.8 |
C4—C5—C6 | 111.8 (4) | | |
| | | |
C8—C7—C1—C2 | 27.6 (6) | C13—C1—C6—C5 | 176.4 (3) |
C12—C7—C1—C2 | −156.9 (4) | C7—C1—C6—C5 | −65.7 (4) |
C8—C7—C1—C13 | −93.4 (5) | C14—C13—C18—C17 | −1.1 (7) |
C12—C7—C1—C13 | 82.2 (5) | C1—C13—C18—C17 | 176.4 (4) |
C8—C7—C1—C6 | 146.5 (4) | C17—C16—C15—C14 | −0.1 (7) |
C12—C7—C1—C6 | −38.0 (5) | O2—C16—C15—C14 | 179.8 (4) |
C12—C7—C8—C9 | 0.0 (6) | C13—C14—C15—C16 | −0.9 (7) |
C1—C7—C8—C9 | 175.7 (4) | C1—C6—C5—C4 | −58.0 (5) |
C2—C1—C13—C14 | −23.0 (6) | C15—C16—C17—C18 | 0.6 (7) |
C6—C1—C13—C14 | −140.7 (4) | O2—C16—C17—C18 | −179.4 (4) |
C7—C1—C13—C14 | 98.5 (5) | C13—C18—C17—C16 | 0.1 (7) |
C2—C1—C13—C18 | 159.6 (4) | C6—C5—C4—C3 | 54.4 (5) |
C6—C1—C13—C18 | 41.9 (5) | C1—C2—C3—C4 | 56.9 (5) |
C7—C1—C13—C18 | −78.9 (5) | C5—C4—C3—C2 | −53.8 (5) |
C11—C10—C9—C8 | 0.2 (6) | C6G—C1G—C2G—C3G | −0.3 (6) |
O1—C10—C9—C8 | −179.9 (4) | N1G—C1G—C2G—C3G | −178.0 (4) |
C7—C8—C9—C10 | −0.1 (6) | C2G—C1G—C6G—C5G | 0.3 (6) |
O1—C10—C11—C12 | −180.0 (4) | N1G—C1G—C6G—C5G | 177.9 (4) |
C9—C10—C11—C12 | −0.1 (6) | C1G—C2G—C3G—C4G | 0.2 (6) |
C13—C1—C2—C3 | −176.0 (4) | C1G—C2G—C3G—C7G | 178.7 (4) |
C6—C1—C2—C3 | −56.1 (4) | C2G—C3G—C4G—C5G | −0.1 (6) |
C7—C1—C2—C3 | 65.6 (5) | C7G—C3G—C4G—C5G | −178.6 (4) |
C10—C11—C12—C7 | −0.1 (7) | C2G—C3G—C4G—C8G | 179.6 (4) |
C8—C7—C12—C11 | 0.1 (6) | C7G—C3G—C4G—C8G | 1.2 (7) |
C1—C7—C12—C11 | −175.6 (4) | C3G—C4G—C5G—C6G | 0.1 (7) |
C18—C13—C14—C15 | 1.5 (7) | C8G—C4G—C5G—C6G | −179.7 (4) |
C1—C13—C14—C15 | −176.0 (4) | C1G—C6G—C5G—C4G | −0.1 (7) |
C2—C1—C6—C5 | 56.2 (4) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.95 (2) | 1.77 (2) | 2.706 (4) | 166 (4) |
O2—H2···N1Gii | 0.97 (2) | 1.78 (2) | 2.744 (5) | 173 (5) |
N1G—H1G1···O1 | 0.98 (2) | 2.02 (2) | 2.975 (5) | 166 (3) |
Symmetry codes: (i) x, −y+2, z−1/2; (ii) x, −y+1, z+1/2. |
(dc35x1) 1,1'-bis-(4-hydroxyphenyl)cyclohexane and 3,5-xylidine
top
Crystal data top
C18H20O2/C8H11N | Z = 2 |
Mr = 389.52 | F(000) = 420 |
Triclinic, P1 | Dx = 1.175 Mg m−3 Dm = N/A Mg m−3 Dm measured by not measured |
a = 6.327 (1) Å | Melting point: 397.35K for guest release onset temp. and 463.15K for host melting K |
b = 10.720 (2) Å | Mo Kα radiation, λ = 0.71069 Å |
c = 16.920 (4) Å | µ = 0.07 mm−1 |
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 tube | Rint = 0.039 |
Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
1° φ scans and ω scans | h = 0→7 |
4014 measured reflections | k = −12→12 |
3869 independent reflections | l = −20→19 |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H 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 reflections | Δρmax = 0.20 e Å−3 |
281 parameters | Δρmin = −0.18 e Å−3 |
7 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction 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 | x | y | z | Uiso*/Ueq | |
O2 | 0.3928 (4) | 0.68002 (18) | 0.72633 (12) | 0.0562 (6) | |
O1 | 0.0728 (3) | −0.18608 (18) | 0.68965 (12) | 0.0554 (6) | |
C7 | 0.1635 (4) | 0.1486 (2) | 0.85554 (15) | 0.0368 (6) | |
C1 | 0.1943 (4) | 0.2764 (2) | 0.91165 (15) | 0.0367 (6) | |
C9 | 0.2994 (4) | −0.0339 (3) | 0.80014 (16) | 0.0438 (7) | |
H9 | 0.4124 | −0.0794 | 0.8009 | 0.053* | |
C13 | 0.2417 (4) | 0.3844 (2) | 0.86143 (15) | 0.0364 (6) | |
C18 | 0.1246 (4) | 0.4822 (3) | 0.85518 (16) | 0.0445 (7) | |
H18 | 0.0078 | 0.4825 | 0.8817 | 0.053* | |
C10 | 0.1063 (4) | −0.0768 (2) | 0.74526 (15) | 0.0410 (7) | |
C15 | 0.4671 (4) | 0.4861 (3) | 0.77511 (17) | 0.0469 (7) | |
H15 | 0.5842 | 0.4867 | 0.7486 | 0.056* | |
C2 | 0.3880 (4) | 0.2939 (2) | 0.98404 (16) | 0.0421 (7) | |
H21 | 0.5193 | 0.2859 | 0.9633 | 0.051* | |
H22 | 0.4105 | 0.3799 | 1.0132 | 0.051* | |
C12 | −0.0291 (4) | 0.1022 (3) | 0.79878 (16) | 0.0451 (7) | |
H12 | −0.1423 | 0.1476 | 0.7974 | 0.054* | |
C17 | 0.1770 (5) | 0.5793 (3) | 0.81052 (16) | 0.0472 (7) | |
H17 | 0.0959 | 0.6439 | 0.8078 | 0.057* | |
C16 | 0.3472 (5) | 0.5814 (2) | 0.77016 (16) | 0.0423 (7) | |
C8 | 0.3265 (4) | 0.0771 (2) | 0.85449 (16) | 0.0428 (7) | |
H8 | 0.4582 | 0.1045 | 0.8915 | 0.051* | |
C11 | −0.0594 (5) | −0.0081 (3) | 0.74460 (16) | 0.0470 (7) | |
H11 | −0.1911 | −0.0363 | 0.7077 | 0.056* | |
C14 | 0.4127 (4) | 0.3893 (3) | 0.81962 (17) | 0.0463 (7) | |
H14 | 0.4939 | 0.3247 | 0.8217 | 0.056* | |
C6 | −0.0097 (4) | 0.2838 (3) | 0.94901 (16) | 0.0435 (7) | |
H61 | 0.0065 | 0.3689 | 0.9787 | 0.052* | |
H62 | −0.1376 | 0.2700 | 0.9057 | 0.052* | |
C5 | −0.0457 (5) | 0.1852 (3) | 1.00624 (17) | 0.0520 (8) | |
H51 | −0.1753 | 0.1938 | 1.0280 | 0.062* | |
H52 | −0.0701 | 0.0998 | 0.9761 | 0.062* | |
C3 | 0.3576 (4) | 0.1986 (3) | 1.04353 (16) | 0.0456 (7) | |
H31 | 0.3517 | 0.1130 | 1.0165 | 0.055* | |
H32 | 0.4819 | 0.2186 | 1.0886 | 0.055* | |
C4 | 0.1493 (5) | 0.2027 (3) | 1.07547 (17) | 0.0547 (8) | |
H41 | 0.1638 | 0.2842 | 1.1093 | 0.066* | |
H42 | 0.1260 | 0.1355 | 1.1087 | 0.066* | |
N1G | 0.3627 (5) | 0.3557 (3) | 0.38669 (15) | 0.0566 (7) | |
C1G | 0.4510 (5) | 0.3065 (3) | 0.45744 (17) | 0.0514 (8) | |
C6G | 0.6615 (5) | 0.3584 (3) | 0.49912 (19) | 0.0604 (9) | |
H6G | 0.7430 | 0.4259 | 0.4808 | 0.072* | |
C2G | 0.3325 (6) | 0.2049 (3) | 0.4840 (2) | 0.0681 (9) | |
H2G | 0.1913 | 0.1686 | 0.4561 | 0.082* | |
C5G | 0.7535 (6) | 0.3125 (3) | 0.5673 (2) | 0.0679 (9) | |
C3G | 0.4218 (7) | 0.1564 (4) | 0.5519 (2) | 0.0815 (12) | |
C4G | 0.6302 (7) | 0.2121 (4) | 0.5931 (2) | 0.0816 (11) | |
H4G | 0.6892 | 0.1811 | 0.6395 | 0.098* | |
C7G | 0.2902 (8) | 0.0446 (5) | 0.5805 (3) | 0.138 (2) | |
H7G1 | 0.3861 | 0.0078 | 0.6176 | 0.207* | |
H7G2 | 0.2186 | −0.0188 | 0.5347 | 0.207* | |
H7G3 | 0.1824 | 0.0740 | 0.6074 | 0.207* | |
C8G | 0.9838 (6) | 0.3696 (4) | 0.6128 (3) | 0.1075 (15) | |
H8G1 | 1.0088 | 0.3379 | 0.6638 | 0.161* | |
H8G2 | 1.0021 | 0.4611 | 0.6223 | 0.161* | |
H8G3 | 1.0866 | 0.3459 | 0.5812 | 0.161* | |
H1G2 | 0.380 (6) | 0.4472 (18) | 0.397 (2) | 0.092 (12)* | |
H1G1 | 0.212 (3) | 0.315 (3) | 0.365 (2) | 0.094 (13)* | |
H2 | 0.486 (6) | 0.667 (4) | 0.6871 (19) | 0.119 (15)* | |
H1 | 0.197 (4) | −0.226 (3) | 0.706 (2) | 0.111 (14)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O2 | 0.0760 (15) | 0.0466 (12) | 0.0604 (13) | 0.0224 (10) | 0.0313 (12) | 0.0249 (10) |
O1 | 0.0680 (15) | 0.0448 (12) | 0.0490 (12) | 0.0140 (11) | 0.0011 (11) | 0.0002 (10) |
C7 | 0.0390 (15) | 0.0402 (15) | 0.0364 (14) | 0.0121 (12) | 0.0126 (12) | 0.0135 (12) |
C1 | 0.0343 (14) | 0.0378 (15) | 0.0412 (15) | 0.0105 (12) | 0.0105 (12) | 0.0101 (12) |
C9 | 0.0444 (17) | 0.0461 (17) | 0.0460 (16) | 0.0191 (13) | 0.0093 (14) | 0.0116 (14) |
C13 | 0.0378 (15) | 0.0383 (15) | 0.0353 (14) | 0.0083 (12) | 0.0105 (12) | 0.0082 (11) |
C18 | 0.0485 (17) | 0.0471 (16) | 0.0464 (16) | 0.0198 (14) | 0.0189 (14) | 0.0111 (13) |
C10 | 0.0521 (18) | 0.0381 (15) | 0.0343 (15) | 0.0098 (13) | 0.0086 (14) | 0.0101 (12) |
C15 | 0.0450 (17) | 0.0503 (17) | 0.0546 (18) | 0.0144 (14) | 0.0228 (14) | 0.0186 (14) |
C2 | 0.0429 (16) | 0.0406 (15) | 0.0434 (16) | 0.0073 (12) | 0.0100 (13) | 0.0075 (12) |
C12 | 0.0417 (16) | 0.0460 (17) | 0.0489 (17) | 0.0161 (13) | 0.0043 (14) | 0.0078 (14) |
C17 | 0.0592 (19) | 0.0413 (16) | 0.0519 (17) | 0.0221 (14) | 0.0236 (15) | 0.0138 (14) |
C16 | 0.0539 (18) | 0.0350 (15) | 0.0402 (15) | 0.0091 (13) | 0.0117 (13) | 0.0105 (12) |
C8 | 0.0413 (16) | 0.0430 (16) | 0.0427 (16) | 0.0096 (13) | 0.0032 (12) | 0.0059 (13) |
C11 | 0.0419 (17) | 0.0492 (17) | 0.0452 (17) | 0.0091 (13) | −0.0026 (13) | 0.0050 (14) |
C14 | 0.0460 (17) | 0.0458 (16) | 0.0567 (18) | 0.0187 (13) | 0.0194 (14) | 0.0193 (14) |
C6 | 0.0411 (16) | 0.0469 (16) | 0.0470 (16) | 0.0126 (13) | 0.0143 (13) | 0.0113 (13) |
C5 | 0.0481 (18) | 0.0597 (19) | 0.0576 (19) | 0.0156 (15) | 0.0239 (15) | 0.0195 (15) |
C3 | 0.0476 (17) | 0.0522 (17) | 0.0374 (15) | 0.0109 (13) | 0.0057 (13) | 0.0100 (13) |
C4 | 0.064 (2) | 0.062 (2) | 0.0477 (18) | 0.0174 (16) | 0.0228 (16) | 0.0200 (15) |
N1G | 0.068 (2) | 0.0575 (18) | 0.0474 (15) | 0.0114 (15) | 0.0158 (14) | 0.0138 (13) |
C1G | 0.060 (2) | 0.0566 (19) | 0.0404 (16) | 0.0119 (15) | 0.0176 (15) | 0.0048 (14) |
C6G | 0.065 (2) | 0.056 (2) | 0.059 (2) | −0.0004 (16) | 0.0190 (17) | 0.0077 (16) |
C2G | 0.065 (2) | 0.078 (2) | 0.056 (2) | −0.0053 (18) | 0.0108 (17) | 0.0189 (18) |
C5G | 0.068 (2) | 0.072 (2) | 0.056 (2) | 0.0076 (19) | 0.0051 (18) | 0.0016 (18) |
C3G | 0.087 (3) | 0.092 (3) | 0.062 (2) | −0.007 (2) | 0.013 (2) | 0.036 (2) |
C4G | 0.090 (3) | 0.096 (3) | 0.053 (2) | 0.008 (2) | 0.002 (2) | 0.022 (2) |
C7G | 0.131 (4) | 0.155 (5) | 0.115 (4) | −0.035 (3) | 0.008 (3) | 0.082 (4) |
C8G | 0.082 (3) | 0.124 (4) | 0.093 (3) | −0.001 (3) | −0.016 (2) | 0.001 (3) |
Geometric parameters (Å, º) top
O2—C16 | 1.378 (3) | C6—C5 | 1.527 (4) |
O2—H2 | 0.978 (14) | C6—H61 | 0.9700 |
O1—C10 | 1.378 (3) | C6—H62 | 0.9700 |
O1—H1 | 0.970 (14) | C5—C4 | 1.515 (4) |
C7—C8 | 1.388 (3) | C5—H51 | 0.9700 |
C7—C12 | 1.389 (4) | C5—H52 | 0.9700 |
C7—C1 | 1.539 (4) | C3—C4 | 1.515 (4) |
C1—C13 | 1.531 (3) | C3—H31 | 0.9700 |
C1—C6 | 1.543 (3) | C3—H32 | 0.9700 |
C1—C2 | 1.543 (3) | C4—H41 | 0.9700 |
C9—C10 | 1.372 (4) | C4—H42 | 0.9700 |
C9—C8 | 1.385 (4) | N1G—C1G | 1.425 (4) |
C9—H9 | 0.9300 | N1G—H1G2 | 0.960 (18) |
C13—C18 | 1.386 (3) | N1G—H1G1 | 0.966 (14) |
C13—C14 | 1.390 (3) | C1G—C2G | 1.379 (4) |
C18—C17 | 1.383 (4) | C1G—C6G | 1.382 (4) |
C18—H18 | 0.9300 | C6G—C5G | 1.379 (4) |
C10—C11 | 1.380 (4) | C6G—H6G | 0.9300 |
C15—C16 | 1.375 (4) | C2G—C3G | 1.385 (5) |
C15—C14 | 1.381 (4) | C2G—H2G | 0.9300 |
C15—H15 | 0.9300 | C5G—C4G | 1.378 (5) |
C2—C3 | 1.525 (3) | C5G—C8G | 1.512 (5) |
C2—H21 | 0.9700 | C3G—C4G | 1.377 (5) |
C2—H22 | 0.9700 | C3G—C7G | 1.515 (5) |
C12—C11 | 1.376 (4) | C4G—H4G | 0.9300 |
C12—H12 | 0.9300 | C7G—H7G1 | 0.9600 |
C17—C16 | 1.371 (4) | C7G—H7G2 | 0.9600 |
C17—H17 | 0.9300 | C7G—H7G3 | 0.9600 |
C8—H8 | 0.9300 | C8G—H8G1 | 0.9600 |
C11—H11 | 0.9300 | C8G—H8G2 | 0.9600 |
C14—H14 | 0.9300 | C8G—H8G3 | 0.9600 |
| | | |
C16—O2—H2 | 116 (2) | C1—C6—H62 | 109.1 |
C10—O1—H1 | 105 (2) | H61—C6—H62 | 107.8 |
C8—C7—C12 | 116.0 (2) | C4—C5—C6 | 111.3 (2) |
C8—C7—C1 | 123.2 (2) | C4—C5—H51 | 109.4 |
C12—C7—C1 | 120.7 (2) | C6—C5—H51 | 109.4 |
C13—C1—C7 | 107.7 (2) | C4—C5—H52 | 109.4 |
C13—C1—C6 | 112.0 (2) | C6—C5—H52 | 109.4 |
C7—C1—C6 | 110.8 (2) | H51—C5—H52 | 108.0 |
C13—C1—C2 | 108.0 (2) | C4—C3—C2 | 111.1 (2) |
C7—C1—C2 | 112.5 (2) | C4—C3—H31 | 109.4 |
C6—C1—C2 | 105.9 (2) | C2—C3—H31 | 109.4 |
C10—C9—C8 | 120.1 (3) | C4—C3—H32 | 109.4 |
C10—C9—H9 | 120.0 | C2—C3—H32 | 109.4 |
C8—C9—H9 | 120.0 | H31—C3—H32 | 108.0 |
C18—C13—C14 | 116.1 (2) | C3—C4—C5 | 110.8 (2) |
C18—C13—C1 | 123.9 (2) | C3—C4—H41 | 109.5 |
C14—C13—C1 | 120.1 (2) | C5—C4—H41 | 109.5 |
C17—C18—C13 | 121.7 (2) | C3—C4—H42 | 109.5 |
C17—C18—H18 | 119.1 | C5—C4—H42 | 109.5 |
C13—C18—H18 | 119.1 | H41—C4—H42 | 108.1 |
C9—C10—O1 | 122.1 (2) | C1G—N1G—H1G2 | 111 (2) |
C9—C10—C11 | 119.3 (3) | C1G—N1G—H1G1 | 112 (2) |
O1—C10—C11 | 118.6 (2) | H1G2—N1G—H1G1 | 112 (3) |
C16—C15—C14 | 119.6 (3) | C2G—C1G—C6G | 119.0 (3) |
C16—C15—H15 | 120.2 | C2G—C1G—N1G | 121.2 (3) |
C14—C15—H15 | 120.2 | C6G—C1G—N1G | 119.8 (3) |
C3—C2—C1 | 114.3 (2) | C5G—C6G—C1G | 121.5 (3) |
C3—C2—H21 | 108.7 | C5G—C6G—H6G | 119.2 |
C1—C2—H21 | 108.7 | C1G—C6G—H6G | 119.2 |
C3—C2—H22 | 108.7 | C1G—C2G—C3G | 120.6 (3) |
C1—C2—H22 | 108.7 | C1G—C2G—H2G | 119.7 |
H21—C2—H22 | 107.6 | C3G—C2G—H2G | 119.7 |
C11—C12—C7 | 122.7 (3) | C4G—C5G—C6G | 118.2 (3) |
C11—C12—H12 | 118.7 | C4G—C5G—C8G | 120.4 (3) |
C7—C12—H12 | 118.7 | C6G—C5G—C8G | 121.4 (3) |
C16—C17—C18 | 120.7 (2) | C4G—C3G—C2G | 119.0 (3) |
C16—C17—H17 | 119.6 | C4G—C3G—C7G | 120.9 (3) |
C18—C17—H17 | 119.6 | C2G—C3G—C7G | 120.2 (4) |
C17—C16—C15 | 119.1 (2) | C3G—C4G—C5G | 121.7 (3) |
C17—C16—O2 | 118.6 (2) | C3G—C4G—H4G | 119.2 |
C15—C16—O2 | 122.3 (2) | C5G—C4G—H4G | 119.2 |
C9—C8—C7 | 122.2 (3) | C3G—C7G—H7G1 | 109.5 |
C9—C8—H8 | 118.9 | C3G—C7G—H7G2 | 109.5 |
C7—C8—H8 | 118.9 | H7G1—C7G—H7G2 | 109.5 |
C12—C11—C10 | 119.7 (3) | C3G—C7G—H7G3 | 109.5 |
C12—C11—H11 | 120.1 | H7G1—C7G—H7G3 | 109.5 |
C10—C11—H11 | 120.1 | H7G2—C7G—H7G3 | 109.5 |
C15—C14—C13 | 122.7 (2) | C5G—C8G—H8G1 | 109.5 |
C15—C14—H14 | 118.6 | C5G—C8G—H8G2 | 109.5 |
C13—C14—H14 | 118.6 | H8G1—C8G—H8G2 | 109.5 |
C5—C6—C1 | 112.6 (2) | C5G—C8G—H8G3 | 109.5 |
C5—C6—H61 | 109.1 | H8G1—C8G—H8G3 | 109.5 |
C1—C6—H61 | 109.1 | H8G2—C8G—H8G3 | 109.5 |
C5—C6—H62 | 109.1 | | |
| | | |
C8—C7—C1—C13 | 99.9 (3) | C12—C7—C8—C9 | 0.1 (4) |
C12—C7—C1—C13 | −76.2 (3) | C1—C7—C8—C9 | −176.1 (2) |
C8—C7—C1—C6 | −137.4 (2) | C7—C12—C11—C10 | −0.3 (4) |
C12—C7—C1—C6 | 46.6 (3) | C9—C10—C11—C12 | 0.0 (4) |
C8—C7—C1—C2 | −19.0 (3) | O1—C10—C11—C12 | −179.2 (2) |
C12—C7—C1—C2 | 164.9 (2) | C16—C15—C14—C13 | −1.0 (4) |
C7—C1—C13—C18 | 126.4 (3) | C18—C13—C14—C15 | 0.9 (4) |
C6—C1—C13—C18 | 4.3 (3) | C1—C13—C14—C15 | −178.2 (3) |
C2—C1—C13—C18 | −111.9 (3) | C13—C1—C6—C5 | −174.1 (2) |
C7—C1—C13—C14 | −54.6 (3) | C7—C1—C6—C5 | 65.7 (3) |
C6—C1—C13—C14 | −176.6 (2) | C2—C1—C6—C5 | −56.6 (3) |
C2—C1—C13—C14 | 67.2 (3) | C1—C6—C5—C4 | 59.0 (3) |
C14—C13—C18—C17 | −0.6 (4) | C1—C2—C3—C4 | −56.0 (3) |
C1—C13—C18—C17 | 178.5 (3) | C2—C3—C4—C5 | 53.3 (3) |
C8—C9—C10—O1 | 179.4 (2) | C6—C5—C4—C3 | −55.3 (3) |
C8—C9—C10—C11 | 0.3 (4) | C2G—C1G—C6G—C5G | −1.3 (5) |
C13—C1—C2—C3 | 175.9 (2) | N1G—C1G—C6G—C5G | −179.3 (3) |
C7—C1—C2—C3 | −65.4 (3) | C6G—C1G—C2G—C3G | 0.7 (5) |
C6—C1—C2—C3 | 55.8 (3) | N1G—C1G—C2G—C3G | 178.7 (3) |
C8—C7—C12—C11 | 0.2 (4) | C1G—C6G—C5G—C4G | 0.4 (5) |
C1—C7—C12—C11 | 176.6 (2) | C1G—C6G—C5G—C8G | −180.0 (3) |
C13—C18—C17—C16 | 0.5 (4) | C1G—C2G—C3G—C4G | 0.7 (6) |
C18—C17—C16—C15 | −0.5 (4) | C1G—C2G—C3G—C7G | −180.0 (4) |
C18—C17—C16—O2 | 179.9 (3) | C2G—C3G—C4G—C5G | −1.7 (6) |
C14—C15—C16—C17 | 0.8 (4) | C7G—C3G—C4G—C5G | 179.0 (4) |
C14—C15—C16—O2 | −179.6 (3) | C6G—C5G—C4G—C3G | 1.1 (6) |
C10—C9—C8—C7 | −0.4 (4) | C8G—C5G—C4G—C3G | −178.6 (4) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H2···N1Gi | 0.98 (1) | 1.72 (1) | 2.697 (3) | 176 (4) |
O1—H1···O2ii | 0.97 (1) | 1.74 (1) | 2.701 (3) | 171 (3) |
N1G—H1G1···O1iii | 0.97 (1) | 2.07 (2) | 3.013 (4) | 165 (3) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y−1, z; (iii) −x, −y, −z+1. |