Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101014627/fr1347sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101014627/fr1347Isup2.hkl |
CCDC reference: 179287
Tetrabenzo-24-crown-8 was prepared as described by Pedersen (1967) and Brown & Foubister (1983). Crystals of (I) were prepared by slow evaporation of a solution in 1,2-dichloroethane.
Four of the 1,2-dichloroethane molecules were found to be disordered. All were modelled over two sites (occupancy factors C73–74 72.5:27.5, C75–76 50:50, C77–78 52.5:47.5, C79–80 78:22) and were freely refined. All non-H atoms were refined anisotropically, and only one (C73A) exhibited unusual elongation of its displacement ellipsoid. All H atoms were placed in calculated positions, refined using a riding model and given an isotropic displacement parameter equal to 1.2 times the equivalent isotropic displacement parameter of the atom to which they were attached, with Cmethylene—H = 0.99 and Carene—H = 0.95 Å. The nine highest peaks in the final difference map (electron density greater than 0.4 e Å-3) were located near Cl atoms.
Data collection: CAD-4-PC (Enraf-Nonius, 1996); cell refinement: CAD-4-PC; data reduction: XCAD4 (Harms, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: PLATON (Spek, 2001).
C32H32O8·3C2H4Cl2 | Z = 4 |
Mr = 841.43 | F(000) = 1752 |
Triclinic, P1 | Dx = 1.418 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 13.478 (2) Å | Cell parameters from 25 reflections |
b = 14.3841 (18) Å | θ = 10.0–14.4° |
c = 21.381 (2) Å | µ = 0.49 mm−1 |
α = 97.144 (10)° | T = 100 K |
β = 97.854 (10)° | Hexagonal rod, colourless |
γ = 103.405 (11)° | 0.56 × 0.34 × 0.23 mm |
V = 3941.6 (9) Å3 |
Enraf-Nonius CAD-4 diffractometer | 12891 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 27.5°, θmin = 2.0° |
ω scans | h = −17→17 |
Absorption correction: ψ-scan (SHELXTL; Bruker, 1997) | k = −18→18 |
Tmin = 0.840, Tmax = 0.884 | l = −20→27 |
25644 measured reflections | 3 standard reflections every 120 min |
18086 independent reflections | intensity decay: 6% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0501P)2 + 2.861P] where P = (Fo2 + 2Fc2)/3 |
18086 reflections | (Δ/σ)max = 0.001 |
1027 parameters | Δρmax = 0.95 e Å−3 |
0 restraints | Δρmin = −0.76 e Å−3 |
0 constraints |
C32H32O8·3C2H4Cl2 | γ = 103.405 (11)° |
Mr = 841.43 | V = 3941.6 (9) Å3 |
Triclinic, P1 | Z = 4 |
a = 13.478 (2) Å | Mo Kα radiation |
b = 14.3841 (18) Å | µ = 0.49 mm−1 |
c = 21.381 (2) Å | T = 100 K |
α = 97.144 (10)° | 0.56 × 0.34 × 0.23 mm |
β = 97.854 (10)° |
Enraf-Nonius CAD-4 diffractometer | 12891 reflections with I > 2σ(I) |
Absorption correction: ψ-scan (SHELXTL; Bruker, 1997) | Rint = 0.025 |
Tmin = 0.840, Tmax = 0.884 | 3 standard reflections every 120 min |
25644 measured reflections | intensity decay: 6% |
18086 independent reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.120 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.95 e Å−3 |
18086 reflections | Δρmin = −0.76 e Å−3 |
1027 parameters |
Experimental. A 1.1 mm collimator was used. |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All e.s.d.'s are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.44016 (11) | 0.09195 (11) | 0.49109 (7) | 0.0196 (4) | |
O2 | 0.52622 (11) | 0.15340 (10) | 0.39864 (7) | 0.0179 (4) | |
O3 | 0.43188 (11) | 0.12168 (11) | 0.26344 (7) | 0.0187 (4) | |
O4 | 0.26313 (11) | 0.16004 (11) | 0.21696 (7) | 0.0184 (4) | |
O5 | 0.12365 (11) | 0.24525 (10) | 0.28704 (7) | 0.0171 (4) | |
O6 | 0.03819 (11) | 0.18540 (10) | 0.37954 (7) | 0.0166 (4) | |
O7 | 0.05773 (11) | 0.01594 (10) | 0.43608 (7) | 0.0165 (4) | |
O8 | 0.22775 (11) | −0.02349 (10) | 0.48229 (7) | 0.0197 (4) | |
C1 | 0.50479 (16) | 0.18322 (16) | 0.50568 (10) | 0.0192 (6) | |
C2 | 0.55107 (16) | 0.21701 (15) | 0.45477 (10) | 0.0183 (6) | |
C3 | 0.61637 (17) | 0.30937 (17) | 0.46397 (11) | 0.0254 (7) | |
C4 | 0.6351 (2) | 0.36853 (18) | 0.52311 (12) | 0.0328 (8) | |
C5 | 0.5905 (2) | 0.33548 (19) | 0.57286 (12) | 0.0356 (8) | |
C6 | 0.52556 (18) | 0.24226 (18) | 0.56454 (11) | 0.0273 (7) | |
C7 | 0.57468 (16) | 0.18429 (16) | 0.34668 (10) | 0.0199 (6) | |
C8 | 0.53091 (16) | 0.10892 (16) | 0.28821 (10) | 0.0201 (6) | |
C9 | 0.37602 (16) | 0.05897 (15) | 0.21049 (10) | 0.0180 (6) | |
C10 | 0.28296 (16) | 0.07956 (15) | 0.18514 (10) | 0.0179 (6) | |
C11 | 0.21948 (17) | 0.01968 (17) | 0.13192 (11) | 0.0246 (7) | |
C12 | 0.24815 (19) | −0.06051 (19) | 0.10349 (12) | 0.0310 (8) | |
C13 | 0.33975 (19) | −0.07967 (18) | 0.12771 (12) | 0.0304 (7) | |
C14 | 0.40402 (17) | −0.02041 (17) | 0.18133 (11) | 0.0238 (7) | |
C15 | 0.17348 (16) | 0.18803 (16) | 0.19016 (10) | 0.0191 (6) | |
C16 | 0.16702 (16) | 0.27612 (15) | 0.23310 (10) | 0.0180 (6) | |
C17 | 0.11182 (15) | 0.31617 (15) | 0.33175 (10) | 0.0158 (5) | |
C18 | 0.06595 (15) | 0.28380 (14) | 0.38320 (10) | 0.0153 (6) | |
C19 | 0.05165 (16) | 0.35017 (15) | 0.43162 (10) | 0.0183 (6) | |
C20 | 0.08309 (17) | 0.44924 (16) | 0.42934 (11) | 0.0214 (6) | |
C21 | 0.12666 (17) | 0.48070 (16) | 0.37873 (11) | 0.0222 (6) | |
C22 | 0.14107 (16) | 0.41449 (15) | 0.32960 (10) | 0.0195 (6) | |
C23 | −0.01802 (16) | 0.14784 (15) | 0.42687 (10) | 0.0173 (6) | |
C24 | −0.03746 (15) | 0.03941 (15) | 0.41408 (10) | 0.0171 (6) | |
C25 | 0.05629 (16) | −0.08002 (14) | 0.42776 (10) | 0.0168 (6) | |
C26 | 0.14913 (17) | −0.10180 (15) | 0.45275 (10) | 0.0194 (6) | |
C27 | 0.15451 (19) | −0.19785 (16) | 0.44672 (12) | 0.0267 (7) | |
C28 | 0.0684 (2) | −0.27133 (16) | 0.41644 (13) | 0.0320 (8) | |
C29 | −0.0221 (2) | −0.25033 (16) | 0.39236 (12) | 0.0293 (7) | |
C30 | −0.02863 (18) | −0.15446 (16) | 0.39791 (10) | 0.0221 (6) | |
C31 | 0.32013 (16) | −0.04311 (16) | 0.51300 (11) | 0.0228 (7) | |
C32 | 0.39558 (17) | 0.05144 (17) | 0.54165 (10) | 0.0227 (7) | |
O11 | 0.90683 (11) | 0.26221 (10) | 0.19633 (7) | 0.0162 (4) | |
O12 | 0.99351 (11) | 0.35766 (10) | 0.11605 (6) | 0.0148 (4) | |
O13 | 0.94295 (10) | 0.52824 (10) | 0.06966 (7) | 0.0155 (4) | |
O14 | 0.76390 (10) | 0.54436 (10) | 0.02110 (7) | 0.0154 (4) | |
O15 | 0.56347 (11) | 0.40120 (10) | 0.00641 (6) | 0.0160 (4) | |
O16 | 0.48426 (11) | 0.32060 (10) | 0.09467 (6) | 0.0160 (4) | |
O17 | 0.58037 (11) | 0.34344 (10) | 0.22864 (7) | 0.0171 (4) | |
O18 | 0.75486 (11) | 0.31350 (10) | 0.27093 (7) | 0.0171 (4) | |
C41 | 0.92428 (15) | 0.20639 (14) | 0.14455 (9) | 0.0146 (5) | |
C42 | 0.97273 (15) | 0.25923 (14) | 0.10039 (10) | 0.0142 (5) | |
C43 | 0.99492 (16) | 0.21039 (15) | 0.04642 (10) | 0.0163 (6) | |
C44 | 0.96801 (17) | 0.10941 (15) | 0.03477 (10) | 0.0206 (6) | |
C45 | 0.92015 (17) | 0.05756 (15) | 0.07719 (11) | 0.0220 (6) | |
C46 | 0.89892 (16) | 0.10654 (15) | 0.13272 (10) | 0.0184 (6) | |
C47 | 1.04060 (15) | 0.41214 (14) | 0.07128 (10) | 0.0152 (6) | |
C48 | 1.04408 (15) | 0.51682 (14) | 0.09118 (10) | 0.0159 (6) | |
C49 | 0.92748 (15) | 0.61883 (14) | 0.08276 (9) | 0.0148 (5) | |
C50 | 0.82871 (15) | 0.62726 (14) | 0.05655 (9) | 0.0149 (6) | |
C51 | 0.80382 (16) | 0.71543 (15) | 0.06843 (10) | 0.0181 (6) | |
C52 | 0.87636 (18) | 0.79480 (15) | 0.10587 (11) | 0.0217 (6) | |
C53 | 0.97391 (18) | 0.78747 (15) | 0.12980 (11) | 0.0222 (6) | |
C54 | 0.99980 (17) | 0.69907 (15) | 0.11820 (10) | 0.0195 (6) | |
C55 | 0.66501 (15) | 0.55172 (15) | −0.00906 (10) | 0.0165 (6) | |
C56 | 0.60341 (16) | 0.45279 (15) | −0.04182 (9) | 0.0171 (6) | |
C57 | 0.50315 (15) | 0.30875 (14) | −0.01313 (10) | 0.0152 (6) | |
C58 | 0.45908 (15) | 0.26466 (14) | 0.03543 (10) | 0.0155 (6) | |
C59 | 0.39594 (16) | 0.17113 (15) | 0.02100 (10) | 0.0186 (6) | |
C60 | 0.37687 (17) | 0.12071 (15) | −0.04161 (11) | 0.0215 (6) | |
C61 | 0.42000 (17) | 0.16368 (16) | −0.08872 (11) | 0.0224 (6) | |
C62 | 0.48314 (16) | 0.25833 (16) | −0.07500 (10) | 0.0199 (6) | |
C63 | 0.43720 (16) | 0.28068 (15) | 0.14469 (10) | 0.0173 (6) | |
C64 | 0.47818 (15) | 0.35112 (15) | 0.20554 (10) | 0.0173 (6) | |
C65 | 0.63353 (15) | 0.40431 (15) | 0.28301 (9) | 0.0160 (5) | |
C66 | 0.72995 (15) | 0.38784 (15) | 0.30665 (9) | 0.0160 (6) | |
C67 | 0.79044 (16) | 0.44533 (16) | 0.36170 (10) | 0.0191 (6) | |
C68 | 0.75655 (17) | 0.52029 (16) | 0.39336 (10) | 0.0214 (6) | |
C69 | 0.66262 (18) | 0.53623 (16) | 0.37022 (10) | 0.0223 (7) | |
C70 | 0.60080 (16) | 0.47836 (15) | 0.31504 (10) | 0.0197 (6) | |
C71 | 0.84898 (15) | 0.28993 (15) | 0.29459 (10) | 0.0170 (6) | |
C72 | 0.86514 (16) | 0.21338 (15) | 0.24519 (10) | 0.0162 (6) | |
Cl3 | 0.34033 (5) | −0.08779 (6) | 0.34147 (4) | 0.0466 (2) | 0.500 |
Cl3A | 0.34033 (5) | −0.08779 (6) | 0.34147 (4) | 0.0466 (2) | 0.500 |
Cl4 | 0.06047 (5) | −0.01284 (5) | 0.26817 (3) | 0.0330 (2) | 0.500 |
Cl4A | 0.06047 (5) | −0.01284 (5) | 0.26817 (3) | 0.0330 (2) | 0.500 |
C75 | 0.2483 (5) | −0.0143 (4) | 0.3309 (3) | 0.0345 (17) | 0.500 |
C75A | 0.2139 (4) | −0.0960 (4) | 0.2931 (2) | 0.0297 (17) | 0.500 |
C76 | 0.1581 (4) | −0.0796 (4) | 0.2843 (2) | 0.0279 (17) | 0.500 |
C76A | 0.1891 (4) | −0.0020 (4) | 0.3111 (2) | 0.0291 (17) | 0.500 |
Cl1 | 0.28376 (8) | 0.48094 (8) | 0.17510 (5) | 0.0267 (3) | 0.730 |
Cl2 | 0.28612 (7) | 0.71324 (7) | 0.18846 (5) | 0.0395 (3) | 0.730 |
C73 | 0.3432 (3) | 0.5700 (3) | 0.24381 (19) | 0.0368 (12) | 0.730 |
C74 | 0.2822 (4) | 0.6445 (3) | 0.25201 (19) | 0.0405 (14) | 0.730 |
Cl5 | 0.38950 (5) | 0.34427 (6) | 0.36654 (3) | 0.0442 (2) | 0.530 |
Cl6 | 0.24267 (4) | 0.23139 (4) | 0.51683 (3) | 0.0272 (2) | 0.530 |
C77 | 0.3411 (4) | 0.3376 (4) | 0.4420 (2) | 0.0282 (14) | 0.530 |
C78 | 0.2865 (3) | 0.2346 (3) | 0.4427 (2) | 0.0236 (14) | 0.530 |
Cl7 | 0.76987 (4) | 0.30031 (4) | −0.00525 (3) | 0.0264 (2) | 0.780 |
Cl8 | 0.62269 (5) | 0.12900 (5) | 0.12354 (3) | 0.0303 (2) | 0.780 |
C79 | 0.6733 (2) | 0.1642 (2) | 0.05273 (15) | 0.0232 (9) | 0.780 |
C80 | 0.7213 (2) | 0.2717 (2) | 0.06447 (14) | 0.0213 (8) | 0.780 |
Cl9 | 0.76092 (6) | 0.95851 (6) | 0.25590 (4) | 0.0522 (3) | |
Cl10 | 0.55863 (6) | 0.78850 (7) | 0.27183 (4) | 0.0537 (3) | |
C81 | 0.7552 (2) | 0.8331 (2) | 0.24898 (13) | 0.0367 (9) | |
C82 | 0.6917 (2) | 0.7841 (2) | 0.29333 (13) | 0.0384 (8) | |
Cl11 | 0.64945 (6) | 0.56941 (5) | 0.16473 (3) | 0.0437 (2) | |
Cl12 | 0.94361 (6) | 0.52501 (6) | 0.24176 (4) | 0.0468 (3) | |
C83 | 0.7546 (2) | 0.51268 (19) | 0.17553 (12) | 0.0405 (9) | |
C84 | 0.8361 (2) | 0.57782 (18) | 0.22696 (12) | 0.0334 (8) | |
Cl1A | 0.3059 (3) | 0.5267 (3) | 0.1952 (2) | 0.0589 (16) | 0.270 |
Cl2A | 0.17795 (17) | 0.66320 (16) | 0.26609 (10) | 0.0304 (6) | 0.270 |
C73A | 0.3134 (9) | 0.6490 (7) | 0.1892 (6) | 0.045 (4) | 0.270 |
C74A | 0.3004 (8) | 0.7049 (10) | 0.2474 (5) | 0.043 (4) | 0.270 |
Cl5A | 0.38950 (5) | 0.34427 (6) | 0.36654 (3) | 0.0442 (2) | 0.470 |
Cl6A | 0.24267 (4) | 0.23139 (4) | 0.51683 (3) | 0.0272 (2) | 0.470 |
C77A | 0.3198 (4) | 0.2572 (4) | 0.4076 (2) | 0.0245 (16) | 0.470 |
C78A | 0.3179 (4) | 0.3129 (4) | 0.4706 (3) | 0.0217 (16) | 0.470 |
Cl7A | 0.76987 (4) | 0.30031 (4) | −0.00525 (3) | 0.0264 (2) | 0.220 |
Cl8A | 0.62269 (5) | 0.12900 (5) | 0.12354 (3) | 0.0303 (2) | 0.220 |
C79A | 0.6837 (7) | 0.2303 (7) | 0.0971 (5) | 0.023 (3) | 0.220 |
C80A | 0.7010 (8) | 0.1988 (7) | 0.0315 (5) | 0.019 (3) | 0.220 |
H3 | 0.64830 | 0.33220 | 0.42990 | 0.0300* | |
H4 | 0.67890 | 0.43220 | 0.52910 | 0.0390* | |
H5 | 0.60400 | 0.37630 | 0.61320 | 0.0430* | |
H6 | 0.49570 | 0.21950 | 0.59930 | 0.0330* | |
H7A | 0.65040 | 0.19290 | 0.35740 | 0.0240* | |
H7B | 0.56170 | 0.24710 | 0.33860 | 0.0240* | |
H8A | 0.57710 | 0.11710 | 0.25600 | 0.0240* | |
H8B | 0.52380 | 0.04320 | 0.29940 | 0.0240* | |
H11 | 0.15650 | 0.03320 | 0.11480 | 0.0290* | |
H12 | 0.20420 | −0.10200 | 0.06730 | 0.0370* | |
H13 | 0.35930 | −0.13380 | 0.10770 | 0.0360* | |
H14 | 0.46710 | −0.03430 | 0.19800 | 0.0290* | |
H15A | 0.11060 | 0.13500 | 0.18740 | 0.0230* | |
H15B | 0.17930 | 0.20270 | 0.14660 | 0.0230* | |
H16A | 0.23690 | 0.32030 | 0.24760 | 0.0220* | |
H16B | 0.12270 | 0.31120 | 0.20980 | 0.0220* | |
H19 | 0.02060 | 0.32850 | 0.46630 | 0.0220* | |
H20 | 0.07430 | 0.49500 | 0.46290 | 0.0260* | |
H21 | 0.14710 | 0.54810 | 0.37730 | 0.0270* | |
H22 | 0.17090 | 0.43670 | 0.29470 | 0.0230* | |
H23A | −0.08450 | 0.16660 | 0.42420 | 0.0210* | |
H23B | 0.02270 | 0.17390 | 0.47020 | 0.0210* | |
H24A | −0.09220 | 0.00920 | 0.43710 | 0.0210* | |
H24B | −0.06030 | 0.01510 | 0.36770 | 0.0210* | |
H27 | 0.21680 | −0.21330 | 0.46320 | 0.0320* | |
H28 | 0.07240 | −0.33680 | 0.41240 | 0.0380* | |
H29 | −0.08040 | −0.30110 | 0.37190 | 0.0350* | |
H30 | −0.09130 | −0.14000 | 0.38120 | 0.0270* | |
H31A | 0.35010 | −0.07970 | 0.48150 | 0.0270* | |
H31B | 0.30420 | −0.08260 | 0.54680 | 0.0270* | |
H32A | 0.35970 | 0.09590 | 0.56290 | 0.0270* | |
H32B | 0.45030 | 0.04110 | 0.57400 | 0.0270* | |
H43 | 1.02860 | 0.24560 | 0.01720 | 0.0200* | |
H44 | 0.98280 | 0.07610 | −0.00270 | 0.0250* | |
H45 | 0.90160 | −0.01120 | 0.06880 | 0.0260* | |
H46 | 0.86700 | 0.07080 | 0.16230 | 0.0220* | |
H47A | 0.99980 | 0.38850 | 0.02770 | 0.0180* | |
H47B | 1.11160 | 0.40440 | 0.07080 | 0.0180* | |
H48A | 1.06270 | 0.53480 | 0.13830 | 0.0190* | |
H48B | 1.09620 | 0.55870 | 0.07150 | 0.0190* | |
H51 | 0.73740 | 0.72170 | 0.05100 | 0.0220* | |
H52 | 0.85830 | 0.85450 | 0.11500 | 0.0260* | |
H53 | 1.02360 | 0.84250 | 0.15420 | 0.0270* | |
H54 | 1.06710 | 0.69400 | 0.13470 | 0.0230* | |
H55A | 0.67410 | 0.59640 | −0.04070 | 0.0200* | |
H55B | 0.62820 | 0.57750 | 0.02330 | 0.0200* | |
H56A | 0.54590 | 0.45790 | −0.07420 | 0.0210* | |
H56B | 0.64800 | 0.41830 | −0.06350 | 0.0210* | |
H59 | 0.36570 | 0.14130 | 0.05350 | 0.0220* | |
H60 | 0.33390 | 0.05650 | −0.05150 | 0.0260* | |
H61 | 0.40690 | 0.12890 | −0.13100 | 0.0270* | |
H62 | 0.51210 | 0.28790 | −0.10790 | 0.0240* | |
H63A | 0.45380 | 0.21810 | 0.14950 | 0.0210* | |
H63B | 0.36100 | 0.26910 | 0.13430 | 0.0210* | |
H64A | 0.48030 | 0.41780 | 0.19760 | 0.0210* | |
H64B | 0.43290 | 0.33590 | 0.23760 | 0.0210* | |
H67 | 0.85500 | 0.43390 | 0.37800 | 0.0230* | |
H68 | 0.79850 | 0.56020 | 0.43090 | 0.0260* | |
H69 | 0.63970 | 0.58700 | 0.39200 | 0.0270* | |
H70 | 0.53600 | 0.48980 | 0.29940 | 0.0240* | |
H71A | 0.84400 | 0.26540 | 0.33560 | 0.0200* | |
H71B | 0.90780 | 0.34820 | 0.30190 | 0.0200* | |
H72A | 0.91390 | 0.17890 | 0.26460 | 0.0190* | |
H72B | 0.79860 | 0.16570 | 0.22690 | 0.0190* | |
H75A | 0.22700 | 0.00540 | 0.37200 | 0.0420* | 0.500 |
H75B | 0.27830 | 0.04450 | 0.31340 | 0.0420* | 0.500 |
H75C | 0.21740 | −0.10720 | 0.24700 | 0.0360* | 0.500 |
H75D | 0.16040 | −0.14990 | 0.30240 | 0.0360* | 0.500 |
H76A | 0.12880 | −0.13790 | 0.30250 | 0.0330* | 0.500 |
H76B | 0.18110 | −0.10080 | 0.24400 | 0.0330* | 0.500 |
H76C | 0.23990 | 0.05130 | 0.29890 | 0.0350* | 0.500 |
H76D | 0.19080 | 0.01140 | 0.35780 | 0.0350* | 0.500 |
H73A | 0.34730 | 0.53840 | 0.28230 | 0.0440* | 0.730 |
H73B | 0.41460 | 0.60200 | 0.23910 | 0.0440* | 0.730 |
H74A | 0.31090 | 0.68840 | 0.29320 | 0.0490* | 0.730 |
H74B | 0.20940 | 0.61180 | 0.25320 | 0.0490* | 0.730 |
H77A | 0.39940 | 0.36040 | 0.47830 | 0.0340* | 0.530 |
H77B | 0.29280 | 0.37950 | 0.44610 | 0.0340* | 0.530 |
H78A | 0.33440 | 0.19230 | 0.43830 | 0.0280* | 0.530 |
H78B | 0.22720 | 0.21190 | 0.40690 | 0.0280* | 0.530 |
H79A | 0.72580 | 0.12890 | 0.04330 | 0.0280* | 0.780 |
H79B | 0.61650 | 0.14720 | 0.01540 | 0.0280* | 0.780 |
H80A | 0.77800 | 0.28940 | 0.10180 | 0.0260* | 0.780 |
H80B | 0.66890 | 0.30750 | 0.07300 | 0.0260* | 0.780 |
H81A | 0.72530 | 0.80150 | 0.20440 | 0.0440* | |
H81B | 0.82640 | 0.82480 | 0.25830 | 0.0440* | |
H82A | 0.71910 | 0.81700 | 0.33790 | 0.0460* | |
H82B | 0.69560 | 0.71590 | 0.29050 | 0.0460* | |
H83A | 0.73080 | 0.44840 | 0.18820 | 0.0490* | |
H83B | 0.78230 | 0.50390 | 0.13520 | 0.0490* | |
H84A | 0.80710 | 0.58770 | 0.26670 | 0.0400* | |
H84B | 0.85980 | 0.64170 | 0.21370 | 0.0400* | |
H73C | 0.38150 | 0.67860 | 0.17830 | 0.0530* | 0.270 |
H73D | 0.25920 | 0.65210 | 0.15380 | 0.0530* | 0.270 |
H74C | 0.31110 | 0.77380 | 0.24210 | 0.0520* | 0.270 |
H74D | 0.35350 | 0.70100 | 0.28320 | 0.0520* | 0.270 |
H77C | 0.24870 | 0.22810 | 0.38380 | 0.0300* | 0.470 |
H77D | 0.35540 | 0.20500 | 0.41300 | 0.0300* | 0.470 |
H78C | 0.28580 | 0.36710 | 0.46430 | 0.0260* | 0.470 |
H78D | 0.38940 | 0.34020 | 0.49420 | 0.0260* | 0.470 |
H79C | 0.64030 | 0.27720 | 0.09630 | 0.0280* | 0.220 |
H79D | 0.75060 | 0.26170 | 0.12560 | 0.0280* | 0.220 |
H80C | 0.63320 | 0.16750 | 0.00390 | 0.0230* | 0.220 |
H80D | 0.74190 | 0.14990 | 0.03310 | 0.0230* | 0.220 |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0194 (7) | 0.0221 (8) | 0.0184 (7) | 0.0049 (6) | 0.0040 (6) | 0.0077 (6) |
O2 | 0.0181 (7) | 0.0180 (7) | 0.0167 (7) | 0.0015 (6) | 0.0024 (6) | 0.0060 (6) |
O3 | 0.0154 (7) | 0.0224 (8) | 0.0182 (7) | 0.0068 (6) | −0.0006 (6) | 0.0027 (6) |
O4 | 0.0159 (7) | 0.0232 (8) | 0.0170 (7) | 0.0085 (6) | 0.0013 (6) | 0.0014 (6) |
O5 | 0.0198 (7) | 0.0178 (7) | 0.0161 (7) | 0.0071 (6) | 0.0059 (6) | 0.0043 (6) |
O6 | 0.0219 (7) | 0.0154 (7) | 0.0152 (7) | 0.0072 (6) | 0.0055 (6) | 0.0058 (6) |
O7 | 0.0154 (7) | 0.0134 (7) | 0.0212 (7) | 0.0046 (5) | 0.0004 (6) | 0.0055 (6) |
O8 | 0.0172 (7) | 0.0176 (7) | 0.0280 (8) | 0.0081 (6) | 0.0046 (6) | 0.0095 (6) |
C1 | 0.0160 (10) | 0.0215 (11) | 0.0213 (11) | 0.0077 (8) | −0.0013 (8) | 0.0070 (8) |
C2 | 0.0148 (9) | 0.0211 (11) | 0.0187 (10) | 0.0062 (8) | −0.0037 (8) | 0.0061 (8) |
C3 | 0.0216 (11) | 0.0245 (12) | 0.0265 (12) | 0.0022 (9) | −0.0044 (9) | 0.0073 (9) |
C4 | 0.0314 (13) | 0.0243 (12) | 0.0334 (14) | −0.0017 (10) | −0.0081 (11) | 0.0016 (10) |
C5 | 0.0398 (15) | 0.0343 (14) | 0.0253 (13) | 0.0072 (11) | −0.0081 (11) | −0.0042 (11) |
C6 | 0.0271 (12) | 0.0329 (13) | 0.0216 (11) | 0.0104 (10) | −0.0019 (9) | 0.0049 (10) |
C7 | 0.0150 (10) | 0.0241 (11) | 0.0205 (11) | 0.0016 (8) | 0.0019 (8) | 0.0105 (9) |
C8 | 0.0155 (10) | 0.0265 (11) | 0.0206 (11) | 0.0077 (8) | 0.0033 (8) | 0.0080 (9) |
C9 | 0.0154 (10) | 0.0226 (11) | 0.0161 (10) | 0.0033 (8) | 0.0043 (8) | 0.0050 (8) |
C10 | 0.0151 (10) | 0.0225 (11) | 0.0175 (10) | 0.0053 (8) | 0.0061 (8) | 0.0041 (8) |
C11 | 0.0186 (11) | 0.0321 (13) | 0.0224 (11) | 0.0086 (9) | 0.0025 (9) | −0.0008 (9) |
C12 | 0.0240 (12) | 0.0347 (14) | 0.0292 (13) | 0.0071 (10) | 0.0006 (10) | −0.0088 (10) |
C13 | 0.0285 (12) | 0.0295 (13) | 0.0325 (13) | 0.0117 (10) | 0.0053 (10) | −0.0059 (10) |
C14 | 0.0205 (11) | 0.0275 (12) | 0.0251 (11) | 0.0097 (9) | 0.0044 (9) | 0.0033 (9) |
C15 | 0.0135 (9) | 0.0295 (12) | 0.0162 (10) | 0.0094 (8) | 0.0009 (8) | 0.0049 (9) |
C16 | 0.0172 (10) | 0.0238 (11) | 0.0148 (10) | 0.0069 (8) | 0.0033 (8) | 0.0064 (8) |
C17 | 0.0135 (9) | 0.0200 (10) | 0.0152 (9) | 0.0083 (8) | 0.0000 (8) | 0.0033 (8) |
C18 | 0.0135 (9) | 0.0160 (10) | 0.0176 (10) | 0.0070 (8) | −0.0012 (8) | 0.0054 (8) |
C19 | 0.0190 (10) | 0.0221 (11) | 0.0161 (10) | 0.0089 (8) | 0.0020 (8) | 0.0053 (8) |
C20 | 0.0234 (11) | 0.0202 (11) | 0.0214 (11) | 0.0102 (9) | 0.0019 (9) | −0.0002 (9) |
C21 | 0.0216 (11) | 0.0152 (10) | 0.0306 (12) | 0.0061 (8) | 0.0035 (9) | 0.0051 (9) |
C22 | 0.0177 (10) | 0.0202 (11) | 0.0230 (11) | 0.0067 (8) | 0.0043 (8) | 0.0075 (9) |
C23 | 0.0183 (10) | 0.0207 (10) | 0.0167 (10) | 0.0082 (8) | 0.0058 (8) | 0.0084 (8) |
C24 | 0.0140 (9) | 0.0203 (10) | 0.0179 (10) | 0.0052 (8) | 0.0012 (8) | 0.0060 (8) |
C25 | 0.0226 (10) | 0.0130 (9) | 0.0163 (10) | 0.0039 (8) | 0.0073 (8) | 0.0050 (8) |
C26 | 0.0246 (11) | 0.0166 (10) | 0.0202 (10) | 0.0061 (8) | 0.0101 (9) | 0.0067 (8) |
C27 | 0.0329 (13) | 0.0211 (11) | 0.0346 (13) | 0.0128 (10) | 0.0191 (11) | 0.0109 (10) |
C28 | 0.0469 (15) | 0.0135 (11) | 0.0428 (15) | 0.0098 (10) | 0.0261 (12) | 0.0073 (10) |
C29 | 0.0367 (14) | 0.0165 (11) | 0.0305 (13) | −0.0022 (10) | 0.0117 (11) | −0.0012 (9) |
C30 | 0.0258 (11) | 0.0199 (11) | 0.0182 (10) | 0.0008 (9) | 0.0045 (9) | 0.0029 (8) |
C31 | 0.0198 (11) | 0.0251 (11) | 0.0307 (12) | 0.0117 (9) | 0.0080 (9) | 0.0164 (10) |
C32 | 0.0213 (11) | 0.0325 (12) | 0.0201 (11) | 0.0120 (9) | 0.0059 (9) | 0.0142 (9) |
O11 | 0.0216 (7) | 0.0148 (7) | 0.0159 (7) | 0.0071 (6) | 0.0078 (6) | 0.0072 (6) |
O12 | 0.0208 (7) | 0.0118 (7) | 0.0140 (7) | 0.0054 (5) | 0.0054 (6) | 0.0048 (5) |
O13 | 0.0154 (7) | 0.0113 (7) | 0.0205 (7) | 0.0051 (5) | 0.0008 (6) | 0.0039 (6) |
O14 | 0.0139 (7) | 0.0129 (7) | 0.0198 (7) | 0.0049 (5) | −0.0004 (6) | 0.0046 (6) |
O15 | 0.0170 (7) | 0.0151 (7) | 0.0142 (7) | 0.0017 (6) | 0.0006 (6) | 0.0031 (5) |
O16 | 0.0170 (7) | 0.0167 (7) | 0.0129 (7) | 0.0021 (6) | 0.0009 (5) | 0.0034 (5) |
O17 | 0.0133 (7) | 0.0216 (8) | 0.0164 (7) | 0.0069 (6) | 0.0000 (6) | 0.0016 (6) |
O18 | 0.0138 (7) | 0.0233 (8) | 0.0147 (7) | 0.0077 (6) | −0.0001 (5) | 0.0017 (6) |
C41 | 0.0140 (9) | 0.0169 (10) | 0.0156 (9) | 0.0078 (8) | 0.0027 (8) | 0.0050 (8) |
C42 | 0.0148 (9) | 0.0130 (9) | 0.0172 (10) | 0.0070 (7) | 0.0012 (8) | 0.0062 (8) |
C43 | 0.0184 (10) | 0.0164 (10) | 0.0184 (10) | 0.0090 (8) | 0.0047 (8) | 0.0084 (8) |
C44 | 0.0277 (11) | 0.0171 (10) | 0.0205 (11) | 0.0123 (9) | 0.0053 (9) | 0.0021 (8) |
C45 | 0.0266 (11) | 0.0124 (10) | 0.0298 (12) | 0.0083 (8) | 0.0070 (9) | 0.0051 (9) |
C46 | 0.0198 (10) | 0.0155 (10) | 0.0228 (11) | 0.0061 (8) | 0.0054 (8) | 0.0091 (8) |
C47 | 0.0146 (9) | 0.0162 (10) | 0.0176 (10) | 0.0049 (8) | 0.0057 (8) | 0.0082 (8) |
C48 | 0.0133 (9) | 0.0150 (10) | 0.0198 (10) | 0.0036 (7) | 0.0004 (8) | 0.0074 (8) |
C49 | 0.0188 (10) | 0.0126 (9) | 0.0144 (9) | 0.0045 (8) | 0.0033 (8) | 0.0060 (7) |
C50 | 0.0183 (10) | 0.0127 (9) | 0.0155 (10) | 0.0036 (8) | 0.0063 (8) | 0.0062 (7) |
C51 | 0.0209 (10) | 0.0168 (10) | 0.0212 (10) | 0.0086 (8) | 0.0075 (8) | 0.0087 (8) |
C52 | 0.0323 (12) | 0.0116 (10) | 0.0250 (11) | 0.0080 (9) | 0.0110 (9) | 0.0064 (8) |
C53 | 0.0290 (12) | 0.0124 (10) | 0.0218 (11) | 0.0001 (8) | 0.0028 (9) | 0.0012 (8) |
C54 | 0.0223 (11) | 0.0162 (10) | 0.0186 (10) | 0.0034 (8) | 0.0003 (8) | 0.0042 (8) |
C55 | 0.0164 (10) | 0.0179 (10) | 0.0178 (10) | 0.0071 (8) | 0.0019 (8) | 0.0083 (8) |
C56 | 0.0184 (10) | 0.0198 (10) | 0.0134 (9) | 0.0047 (8) | 0.0005 (8) | 0.0063 (8) |
C57 | 0.0124 (9) | 0.0157 (10) | 0.0180 (10) | 0.0055 (7) | −0.0009 (8) | 0.0047 (8) |
C58 | 0.0134 (9) | 0.0167 (10) | 0.0173 (10) | 0.0078 (8) | −0.0010 (8) | 0.0028 (8) |
C59 | 0.0167 (10) | 0.0165 (10) | 0.0226 (11) | 0.0049 (8) | 0.0007 (8) | 0.0049 (8) |
C60 | 0.0215 (11) | 0.0138 (10) | 0.0264 (11) | 0.0041 (8) | −0.0015 (9) | −0.0006 (8) |
C61 | 0.0230 (11) | 0.0218 (11) | 0.0198 (11) | 0.0081 (9) | −0.0034 (9) | −0.0028 (9) |
C62 | 0.0206 (10) | 0.0218 (11) | 0.0182 (10) | 0.0065 (8) | 0.0021 (8) | 0.0055 (8) |
C63 | 0.0144 (9) | 0.0206 (10) | 0.0167 (10) | 0.0030 (8) | 0.0023 (8) | 0.0059 (8) |
C64 | 0.0122 (9) | 0.0230 (11) | 0.0173 (10) | 0.0062 (8) | 0.0012 (8) | 0.0039 (8) |
C65 | 0.0157 (9) | 0.0186 (10) | 0.0132 (9) | 0.0022 (8) | 0.0022 (8) | 0.0050 (8) |
C66 | 0.0163 (10) | 0.0182 (10) | 0.0143 (9) | 0.0030 (8) | 0.0058 (8) | 0.0053 (8) |
C67 | 0.0162 (10) | 0.0249 (11) | 0.0162 (10) | 0.0033 (8) | 0.0022 (8) | 0.0075 (8) |
C68 | 0.0244 (11) | 0.0214 (11) | 0.0139 (10) | −0.0010 (9) | 0.0015 (8) | 0.0008 (8) |
C69 | 0.0281 (12) | 0.0193 (11) | 0.0198 (11) | 0.0068 (9) | 0.0062 (9) | 0.0004 (8) |
C70 | 0.0182 (10) | 0.0222 (11) | 0.0210 (11) | 0.0079 (8) | 0.0045 (8) | 0.0054 (9) |
C71 | 0.0137 (9) | 0.0234 (11) | 0.0158 (10) | 0.0069 (8) | 0.0018 (8) | 0.0075 (8) |
C72 | 0.0167 (10) | 0.0182 (10) | 0.0169 (10) | 0.0061 (8) | 0.0044 (8) | 0.0104 (8) |
Cl3 | 0.0301 (3) | 0.0678 (5) | 0.0416 (4) | 0.0044 (3) | 0.0039 (3) | 0.0251 (4) |
Cl3A | 0.0301 (3) | 0.0678 (5) | 0.0416 (4) | 0.0044 (3) | 0.0039 (3) | 0.0251 (4) |
Cl4 | 0.0436 (4) | 0.0313 (3) | 0.0273 (3) | 0.0138 (3) | 0.0102 (3) | 0.0037 (2) |
Cl4A | 0.0436 (4) | 0.0313 (3) | 0.0273 (3) | 0.0138 (3) | 0.0102 (3) | 0.0037 (2) |
C75 | 0.034 (3) | 0.039 (3) | 0.025 (3) | −0.005 (3) | 0.005 (2) | 0.012 (2) |
C75A | 0.030 (3) | 0.031 (3) | 0.025 (3) | 0.002 (2) | 0.003 (2) | 0.006 (2) |
C76 | 0.029 (3) | 0.028 (3) | 0.024 (3) | 0.004 (2) | 0.000 (2) | 0.005 (2) |
C76A | 0.037 (3) | 0.025 (3) | 0.021 (3) | −0.002 (2) | 0.010 (2) | 0.001 (2) |
Cl1 | 0.0280 (4) | 0.0262 (5) | 0.0273 (5) | 0.0072 (4) | 0.0035 (4) | 0.0108 (4) |
Cl2 | 0.0392 (5) | 0.0351 (5) | 0.0438 (5) | 0.0082 (4) | 0.0013 (4) | 0.0138 (4) |
C73 | 0.038 (2) | 0.036 (2) | 0.030 (2) | 0.0077 (16) | −0.0100 (16) | 0.0013 (17) |
C74 | 0.058 (3) | 0.035 (2) | 0.030 (2) | 0.014 (2) | 0.0025 (18) | 0.0120 (18) |
Cl5 | 0.0288 (3) | 0.0839 (6) | 0.0280 (3) | 0.0206 (3) | 0.0081 (3) | 0.0237 (3) |
Cl6 | 0.0253 (3) | 0.0265 (3) | 0.0305 (3) | 0.0063 (2) | 0.0043 (2) | 0.0088 (2) |
C77 | 0.024 (2) | 0.041 (3) | 0.022 (2) | 0.007 (2) | 0.007 (2) | 0.013 (2) |
C78 | 0.019 (2) | 0.031 (3) | 0.021 (2) | 0.0125 (18) | −0.0014 (18) | −0.0009 (19) |
Cl7 | 0.0219 (3) | 0.0202 (3) | 0.0365 (3) | 0.0054 (2) | −0.0003 (2) | 0.0076 (2) |
Cl8 | 0.0317 (3) | 0.0395 (3) | 0.0246 (3) | 0.0154 (3) | 0.0075 (2) | 0.0081 (2) |
C79 | 0.0246 (16) | 0.0244 (17) | 0.0218 (16) | 0.0080 (13) | 0.0042 (13) | 0.0041 (13) |
C80 | 0.0194 (13) | 0.0215 (15) | 0.0231 (14) | 0.0092 (11) | −0.0010 (12) | 0.0009 (12) |
Cl9 | 0.0498 (4) | 0.0427 (4) | 0.0533 (5) | −0.0052 (3) | −0.0073 (4) | 0.0174 (3) |
Cl10 | 0.0307 (4) | 0.0814 (6) | 0.0438 (4) | −0.0013 (4) | 0.0081 (3) | 0.0186 (4) |
C81 | 0.0286 (13) | 0.0491 (17) | 0.0324 (14) | 0.0068 (12) | 0.0047 (11) | 0.0132 (12) |
C82 | 0.0332 (14) | 0.0465 (16) | 0.0343 (14) | 0.0040 (12) | 0.0077 (12) | 0.0112 (12) |
Cl11 | 0.0427 (4) | 0.0490 (4) | 0.0280 (3) | −0.0105 (3) | −0.0053 (3) | 0.0172 (3) |
Cl12 | 0.0640 (5) | 0.0486 (4) | 0.0491 (4) | 0.0332 (4) | 0.0311 (4) | 0.0284 (3) |
C83 | 0.066 (2) | 0.0259 (13) | 0.0241 (13) | −0.0040 (13) | 0.0123 (13) | 0.0079 (10) |
C84 | 0.0475 (16) | 0.0274 (13) | 0.0278 (13) | 0.0097 (11) | 0.0107 (12) | 0.0088 (10) |
Cl1A | 0.070 (3) | 0.045 (2) | 0.083 (3) | 0.032 (2) | 0.039 (2) | 0.029 (2) |
Cl2A | 0.0296 (11) | 0.0309 (11) | 0.0267 (10) | −0.0012 (9) | −0.0001 (8) | 0.0116 (9) |
C73A | 0.060 (7) | 0.023 (5) | 0.064 (7) | 0.029 (5) | 0.014 (6) | 0.019 (5) |
C74A | 0.038 (6) | 0.052 (7) | 0.039 (6) | 0.002 (5) | 0.004 (5) | 0.025 (6) |
Cl5A | 0.0288 (3) | 0.0839 (6) | 0.0280 (3) | 0.0206 (3) | 0.0081 (3) | 0.0237 (3) |
Cl6A | 0.0253 (3) | 0.0265 (3) | 0.0305 (3) | 0.0063 (2) | 0.0043 (2) | 0.0088 (2) |
C77A | 0.020 (2) | 0.030 (3) | 0.025 (3) | 0.010 (2) | 0.001 (2) | 0.006 (2) |
C78A | 0.019 (2) | 0.022 (3) | 0.024 (3) | 0.0060 (19) | 0.003 (2) | 0.003 (2) |
Cl7A | 0.0219 (3) | 0.0202 (3) | 0.0365 (3) | 0.0054 (2) | −0.0003 (2) | 0.0076 (2) |
Cl8A | 0.0317 (3) | 0.0395 (3) | 0.0246 (3) | 0.0154 (3) | 0.0075 (2) | 0.0081 (2) |
C79A | 0.012 (4) | 0.020 (5) | 0.035 (6) | 0.004 (4) | −0.002 (4) | −0.001 (5) |
C80A | 0.019 (5) | 0.013 (5) | 0.027 (6) | 0.005 (4) | 0.001 (4) | 0.009 (5) |
Cl3—C75 | 1.816 (7) | C32—H32A | 0.9902 |
Cl3A—C75A | 1.839 (5) | C41—C42 | 1.419 (3) |
Cl4—C76 | 1.821 (6) | C41—C46 | 1.379 (3) |
Cl4A—C76A | 1.810 (5) | C42—C43 | 1.380 (3) |
Cl1—C73 | 1.782 (4) | C43—C44 | 1.394 (3) |
Cl2—C74 | 1.777 (4) | C44—C45 | 1.378 (3) |
Cl5—C77 | 1.826 (5) | C45—C46 | 1.402 (3) |
Cl6—C78 | 1.768 (4) | C47—C48 | 1.501 (3) |
Cl7—C80 | 1.765 (3) | C49—C50 | 1.410 (3) |
Cl8—C79 | 1.824 (3) | C49—C54 | 1.384 (3) |
Cl9—C81 | 1.774 (3) | C50—C51 | 1.388 (3) |
Cl10—C82 | 1.807 (3) | C51—C52 | 1.393 (3) |
Cl11—C83 | 1.795 (3) | C52—C53 | 1.377 (3) |
Cl12—C84 | 1.795 (3) | C53—C54 | 1.397 (3) |
Cl1A—C73A | 1.760 (11) | C55—C56 | 1.500 (3) |
Cl2A—C74A | 1.739 (12) | C57—C58 | 1.411 (3) |
Cl5A—C77A | 1.782 (5) | C57—C62 | 1.386 (3) |
Cl6A—C78A | 1.841 (6) | C58—C59 | 1.387 (3) |
Cl7A—C80A | 1.862 (10) | C59—C60 | 1.401 (3) |
Cl8A—C79A | 1.702 (10) | C60—C61 | 1.372 (3) |
O1—C32 | 1.429 (3) | C61—C62 | 1.400 (3) |
O1—C1 | 1.369 (3) | C63—C64 | 1.497 (3) |
O2—C7 | 1.430 (3) | C65—C66 | 1.412 (3) |
O2—C2 | 1.365 (3) | C65—C70 | 1.385 (3) |
O3—C9 | 1.364 (3) | C66—C67 | 1.385 (3) |
O3—C8 | 1.428 (3) | C67—C68 | 1.400 (3) |
O4—C15 | 1.430 (3) | C68—C69 | 1.375 (3) |
O4—C10 | 1.368 (3) | C69—C70 | 1.394 (3) |
O5—C17 | 1.362 (3) | C71—C72 | 1.503 (3) |
O5—C16 | 1.435 (3) | C43—H43 | 0.9500 |
O6—C23 | 1.430 (3) | C44—H44 | 0.9506 |
O6—C18 | 1.367 (2) | C45—H45 | 0.9497 |
O7—C25 | 1.365 (2) | C46—H46 | 0.9498 |
O7—C24 | 1.434 (3) | C47—H47A | 0.9903 |
O8—C26 | 1.370 (3) | C47—H47B | 0.9900 |
O8—C31 | 1.431 (3) | C48—H48A | 0.9904 |
O11—C72 | 1.435 (3) | C48—H48B | 0.9905 |
O11—C41 | 1.365 (2) | C51—H51 | 0.9503 |
O12—C42 | 1.367 (2) | C52—H52 | 0.9503 |
O12—C47 | 1.434 (2) | C53—H53 | 0.9504 |
O13—C49 | 1.368 (2) | C54—H54 | 0.9498 |
O13—C48 | 1.431 (3) | C55—H55B | 0.9888 |
O14—C55 | 1.432 (3) | C55—H55A | 0.9899 |
O14—C50 | 1.368 (2) | C56—H56A | 0.9889 |
O15—C56 | 1.436 (2) | C56—H56B | 0.9896 |
O15—C57 | 1.368 (2) | C59—H59 | 0.9506 |
O16—C63 | 1.430 (3) | C60—H60 | 0.9503 |
O16—C58 | 1.367 (2) | C61—H61 | 0.9495 |
O17—C64 | 1.432 (3) | C62—H62 | 0.9490 |
O17—C65 | 1.364 (2) | C63—H63B | 0.9905 |
O18—C71 | 1.431 (3) | C63—H63A | 0.9905 |
O18—C66 | 1.369 (3) | C64—H64B | 0.9899 |
C1—C2 | 1.410 (3) | C64—H64A | 0.9893 |
C1—C6 | 1.382 (3) | C67—H67 | 0.9504 |
C2—C3 | 1.387 (3) | C68—H68 | 0.9510 |
C3—C4 | 1.390 (3) | C69—H69 | 0.9513 |
C4—C5 | 1.374 (4) | C70—H70 | 0.9498 |
C5—C6 | 1.396 (4) | C71—H71A | 0.9899 |
C7—C8 | 1.500 (3) | C71—H71B | 0.9904 |
C9—C14 | 1.386 (3) | C72—H72A | 0.9889 |
C9—C10 | 1.407 (3) | C72—H72B | 0.9899 |
C10—C11 | 1.385 (3) | C75—C76 | 1.503 (8) |
C11—C12 | 1.395 (4) | C75A—C76A | 1.484 (8) |
C12—C13 | 1.374 (4) | C75—H75A | 0.9898 |
C13—C14 | 1.391 (3) | C75—H75B | 0.9901 |
C15—C16 | 1.497 (3) | C75A—H75D | 0.9894 |
C17—C18 | 1.410 (3) | C75A—H75C | 0.9882 |
C17—C22 | 1.386 (3) | C76—H76A | 0.9901 |
C18—C19 | 1.384 (3) | C76—H76B | 0.9915 |
C19—C20 | 1.398 (3) | C76A—H76D | 0.9892 |
C20—C21 | 1.376 (3) | C76A—H76C | 0.9898 |
C21—C22 | 1.393 (3) | C73—C74 | 1.502 (7) |
C23—C24 | 1.504 (3) | C73—H73A | 0.9895 |
C25—C26 | 1.411 (3) | C73—H73B | 0.9903 |
C25—C30 | 1.388 (3) | C74—H74B | 0.9902 |
C26—C27 | 1.391 (3) | C74—H74A | 0.9896 |
C27—C28 | 1.392 (4) | C77—C78 | 1.497 (7) |
C28—C29 | 1.372 (4) | C77—H77A | 0.9889 |
C29—C30 | 1.394 (3) | C77—H77B | 0.9895 |
C31—C32 | 1.497 (3) | C78—H78B | 0.9904 |
C3—H3 | 0.9504 | C78—H78A | 0.9901 |
C4—H4 | 0.9503 | C79—C80 | 1.506 (4) |
C5—H5 | 0.9505 | C79—H79A | 0.9896 |
C6—H6 | 0.9501 | C79—H79B | 0.9902 |
C7—H7A | 0.9899 | C80—H80B | 0.9888 |
C7—H7B | 0.9902 | C80—H80A | 0.9892 |
C8—H8B | 0.9902 | C81—C82 | 1.496 (4) |
C8—H8A | 0.9895 | C81—H81A | 0.9899 |
C11—H11 | 0.9496 | C81—H81B | 0.9908 |
C12—H12 | 0.9496 | C82—H82B | 0.9893 |
C13—H13 | 0.9496 | C82—H82A | 0.9895 |
C14—H14 | 0.9505 | C83—C84 | 1.493 (4) |
C15—H15B | 0.9896 | C83—H83A | 0.9898 |
C15—H15A | 0.9894 | C83—H83B | 0.9908 |
C16—H16A | 0.9903 | C84—H84A | 0.9907 |
C16—H16B | 0.9902 | C84—H84B | 0.9900 |
C19—H19 | 0.9507 | C73A—C74A | 1.450 (17) |
C20—H20 | 0.9508 | C73A—H73C | 0.9899 |
C21—H21 | 0.9500 | C73A—H73D | 0.9904 |
C22—H22 | 0.9499 | C74A—H74D | 0.9904 |
C23—H23A | 0.9904 | C74A—H74C | 0.9909 |
C23—H23B | 0.9896 | C77A—C78A | 1.486 (8) |
C24—H24B | 0.9904 | C77A—H77C | 0.9901 |
C24—H24A | 0.9895 | C77A—H77D | 0.9904 |
C27—H27 | 0.9505 | C78A—H78D | 0.9899 |
C28—H28 | 0.9496 | C78A—H78C | 0.9898 |
C29—H29 | 0.9501 | C79A—C80A | 1.486 (15) |
C30—H30 | 0.9497 | C79A—H79C | 0.9903 |
C31—H31B | 0.9894 | C79A—H79D | 0.9904 |
C31—H31A | 0.9892 | C80A—H80C | 0.9908 |
C32—H32B | 0.9907 | C80A—H80D | 0.9902 |
C1—O1—C32 | 117.65 (16) | C45—C44—H44 | 119.77 |
C2—O2—C7 | 116.70 (16) | C44—C45—H45 | 120.03 |
C8—O3—C9 | 117.42 (17) | C46—C45—H45 | 120.10 |
C10—O4—C15 | 117.01 (16) | C45—C46—H46 | 119.86 |
C16—O5—C17 | 116.51 (16) | C41—C46—H46 | 119.90 |
C18—O6—C23 | 117.08 (16) | O12—C47—H47A | 110.00 |
C24—O7—C25 | 116.46 (16) | H47A—C47—H47B | 108.42 |
C26—O8—C31 | 116.94 (16) | C48—C47—H47B | 109.98 |
C41—O11—C72 | 117.41 (16) | O12—C47—H47B | 110.04 |
C42—O12—C47 | 115.75 (15) | C48—C47—H47A | 109.99 |
C48—O13—C49 | 117.27 (15) | C47—C48—H48A | 110.31 |
C50—O14—C55 | 116.67 (16) | O13—C48—H48B | 110.33 |
C56—O15—C57 | 117.40 (15) | C47—C48—H48B | 110.39 |
C58—O16—C63 | 116.89 (16) | H48A—C48—H48B | 108.62 |
C64—O17—C65 | 117.37 (16) | O13—C48—H48A | 110.37 |
C66—O18—C71 | 116.95 (16) | C50—C51—H51 | 120.04 |
O1—C1—C6 | 125.3 (2) | C52—C51—H51 | 120.02 |
C2—C1—C6 | 119.6 (2) | C51—C52—H52 | 119.69 |
O1—C1—C2 | 115.01 (18) | C53—C52—H52 | 119.72 |
C1—C2—C3 | 119.8 (2) | C54—C53—H53 | 120.02 |
O2—C2—C1 | 115.35 (19) | C52—C53—H53 | 120.04 |
O2—C2—C3 | 124.86 (19) | C49—C54—H54 | 119.96 |
C2—C3—C4 | 119.9 (2) | C53—C54—H54 | 119.96 |
C3—C4—C5 | 120.3 (2) | H55A—C55—H55B | 108.38 |
C4—C5—C6 | 120.4 (2) | O14—C55—H55A | 109.99 |
C1—C6—C5 | 119.9 (2) | O14—C55—H55B | 109.99 |
O2—C7—C8 | 108.71 (18) | C56—C55—H55A | 109.97 |
O3—C8—C7 | 107.00 (18) | C56—C55—H55B | 109.99 |
O3—C9—C14 | 125.4 (2) | O15—C56—H56B | 110.17 |
C10—C9—C14 | 119.6 (2) | C55—C56—H56A | 110.25 |
O3—C9—C10 | 115.00 (19) | O15—C56—H56A | 110.21 |
C9—C10—C11 | 119.8 (2) | C55—C56—H56B | 110.26 |
O4—C10—C9 | 115.01 (18) | H56A—C56—H56B | 108.56 |
O4—C10—C11 | 125.2 (2) | C58—C59—H59 | 120.11 |
C10—C11—C12 | 119.9 (2) | C60—C59—H59 | 120.08 |
C11—C12—C13 | 120.2 (2) | C61—C60—H60 | 119.87 |
C12—C13—C14 | 120.5 (2) | C59—C60—H60 | 119.88 |
C9—C14—C13 | 120.0 (2) | C60—C61—H61 | 119.71 |
O4—C15—C16 | 107.44 (17) | C62—C61—H61 | 119.71 |
O5—C16—C15 | 108.06 (17) | C61—C62—H62 | 120.17 |
C18—C17—C22 | 119.65 (19) | C57—C62—H62 | 120.12 |
O5—C17—C22 | 124.92 (19) | C64—C63—H63A | 109.99 |
O5—C17—C18 | 115.43 (18) | O16—C63—H63B | 110.04 |
O6—C18—C17 | 114.51 (18) | C64—C63—H63B | 110.05 |
O6—C18—C19 | 125.50 (19) | H63A—C63—H63B | 108.41 |
C17—C18—C19 | 119.99 (19) | O16—C63—H63A | 110.05 |
C18—C19—C20 | 119.7 (2) | O17—C64—H64A | 110.11 |
C19—C20—C21 | 120.2 (2) | O17—C64—H64B | 110.15 |
C20—C21—C22 | 120.5 (2) | C63—C64—H64A | 110.19 |
C17—C22—C21 | 119.9 (2) | C63—C64—H64B | 110.14 |
O6—C23—C24 | 107.41 (17) | H64A—C64—H64B | 108.45 |
O7—C24—C23 | 107.54 (17) | C68—C67—H67 | 120.00 |
C26—C25—C30 | 119.74 (19) | C66—C67—H67 | 119.97 |
O7—C25—C30 | 124.8 (2) | C67—C68—H68 | 119.98 |
O7—C25—C26 | 115.49 (18) | C69—C68—H68 | 119.97 |
O8—C26—C25 | 115.27 (18) | C70—C69—H69 | 119.83 |
O8—C26—C27 | 125.3 (2) | C68—C69—H69 | 119.80 |
C25—C26—C27 | 119.4 (2) | C69—C70—H70 | 119.84 |
C26—C27—C28 | 119.8 (2) | C65—C70—H70 | 119.92 |
C27—C28—C29 | 120.8 (2) | O18—C71—H71B | 110.16 |
C28—C29—C30 | 120.0 (2) | C72—C71—H71A | 110.19 |
C25—C30—C29 | 120.2 (2) | O18—C71—H71A | 110.17 |
O8—C31—C32 | 108.33 (18) | C72—C71—H71B | 110.19 |
O1—C32—C31 | 107.78 (17) | H71A—C71—H71B | 108.56 |
C4—C3—H3 | 120.02 | H72A—C72—H72B | 108.64 |
C2—C3—H3 | 120.07 | C71—C72—H72A | 110.39 |
C5—C4—H4 | 119.87 | C71—C72—H72B | 110.33 |
C3—C4—H4 | 119.79 | O11—C72—H72A | 110.36 |
C6—C5—H5 | 119.82 | O11—C72—H72B | 110.37 |
C4—C5—H5 | 119.79 | Cl3—C75—C76 | 104.1 (4) |
C1—C6—H6 | 120.10 | Cl3A—C75A—C76A | 106.1 (3) |
C5—C6—H6 | 120.00 | Cl4—C76—C75 | 108.5 (4) |
O2—C7—H7B | 109.97 | Cl4A—C76A—C75A | 106.4 (4) |
H7A—C7—H7B | 108.35 | Cl3—C75—H75A | 110.91 |
O2—C7—H7A | 109.91 | Cl3—C75—H75B | 110.96 |
C8—C7—H7A | 109.94 | C76—C75—H75A | 110.90 |
C8—C7—H7B | 109.97 | C76—C75—H75B | 110.97 |
C7—C8—H8B | 110.37 | H75A—C75—H75B | 108.93 |
O3—C8—H8B | 110.35 | Cl3A—C75A—H75C | 110.54 |
O3—C8—H8A | 110.36 | Cl3A—C75A—H75D | 110.47 |
H8A—C8—H8B | 108.47 | C76A—C75A—H75C | 110.52 |
C7—C8—H8A | 110.30 | C76A—C75A—H75D | 110.49 |
C10—C11—H11 | 120.02 | H75C—C75A—H75D | 108.67 |
C12—C11—H11 | 120.05 | Cl4—C76—H76A | 110.07 |
C13—C12—H12 | 119.90 | Cl4—C76—H76B | 109.95 |
C11—C12—H12 | 119.91 | C75—C76—H76A | 110.05 |
C12—C13—H13 | 119.74 | C75—C76—H76B | 110.02 |
C14—C13—H13 | 119.78 | H76A—C76—H76B | 108.27 |
C9—C14—H14 | 119.98 | Cl4A—C76A—H76C | 110.51 |
C13—C14—H14 | 120.06 | Cl4A—C76A—H76D | 110.50 |
O4—C15—H15B | 110.25 | H76C—C76A—H76D | 108.66 |
C16—C15—H15A | 110.20 | Cl1—C73—C74 | 110.5 (3) |
C16—C15—H15B | 110.21 | Cl2—C74—C73 | 111.1 (3) |
O4—C15—H15A | 110.21 | Cl1—C73—H73A | 109.54 |
H15A—C15—H15B | 108.53 | Cl1—C73—H73B | 109.57 |
H16A—C16—H16B | 108.38 | C74—C73—H73A | 109.54 |
O5—C16—H16A | 110.16 | C74—C73—H73B | 109.56 |
C15—C16—H16B | 110.11 | H73A—C73—H73B | 108.05 |
C15—C16—H16A | 110.05 | Cl2—C74—H74A | 109.41 |
O5—C16—H16B | 110.08 | Cl2—C74—H74B | 109.45 |
C20—C19—H19 | 120.15 | C73—C74—H74A | 109.49 |
C18—C19—H19 | 120.13 | C73—C74—H74B | 109.42 |
C19—C20—H20 | 119.85 | H74A—C74—H74B | 107.96 |
C21—C20—H20 | 119.91 | Cl5—C77—C78 | 108.5 (3) |
C20—C21—H21 | 119.72 | Cl6—C78—C77 | 106.9 (3) |
C22—C21—H21 | 119.77 | Cl5—C77—H77A | 109.90 |
C17—C22—H22 | 120.06 | Cl5—C77—H77B | 109.94 |
C21—C22—H22 | 120.06 | C78—C77—H77A | 110.07 |
H23A—C23—H23B | 108.48 | C78—C77—H77B | 110.07 |
C24—C23—H23B | 110.23 | H77A—C77—H77B | 108.36 |
C24—C23—H23A | 110.25 | Cl6—C78—H78A | 110.29 |
O6—C23—H23A | 110.26 | Cl6—C78—H78B | 110.32 |
O6—C23—H23B | 110.21 | C77—C78—H78A | 110.37 |
C23—C24—H24A | 110.21 | C77—C78—H78B | 110.31 |
C23—C24—H24B | 110.17 | H78A—C78—H78B | 108.65 |
H24A—C24—H24B | 108.52 | Cl8—C79—C80 | 109.3 (2) |
O7—C24—H24A | 110.18 | Cl7—C80—C79 | 106.9 (2) |
O7—C24—H24B | 110.22 | Cl8—C79—H79A | 109.76 |
C26—C27—H27 | 120.11 | Cl8—C79—H79B | 109.78 |
C28—C27—H27 | 120.07 | C80—C79—H79A | 109.90 |
C27—C28—H28 | 119.56 | C80—C79—H79B | 109.78 |
C29—C28—H28 | 119.60 | H79A—C79—H79B | 108.26 |
C30—C29—H29 | 119.91 | Cl7—C80—H80A | 110.30 |
C28—C29—H29 | 120.07 | Cl7—C80—H80B | 110.36 |
C25—C30—H30 | 119.90 | C79—C80—H80A | 110.35 |
C29—C30—H30 | 119.95 | C79—C80—H80B | 110.36 |
H31A—C31—H31B | 108.31 | H80A—C80—H80B | 108.57 |
O8—C31—H31A | 110.05 | Cl9—C81—C82 | 112.6 (2) |
C32—C31—H31B | 110.06 | Cl10—C82—C81 | 109.56 (19) |
C32—C31—H31A | 110.03 | Cl9—C81—H81A | 109.11 |
O8—C31—H31B | 110.06 | Cl9—C81—H81B | 109.10 |
O1—C32—H32B | 110.17 | C82—C81—H81A | 109.07 |
C31—C32—H32A | 110.12 | C82—C81—H81B | 109.09 |
C31—C32—H32B | 110.13 | H81A—C81—H81B | 107.77 |
H32A—C32—H32B | 108.44 | Cl10—C82—H82A | 109.70 |
O1—C32—H32A | 110.20 | Cl10—C82—H82B | 109.75 |
O11—C41—C46 | 125.79 (18) | C81—C82—H82A | 109.73 |
C42—C41—C46 | 119.54 (18) | C81—C82—H82B | 109.73 |
O11—C41—C42 | 114.67 (17) | H82A—C82—H82B | 108.35 |
O12—C42—C41 | 115.02 (17) | Cl11—C83—C84 | 106.99 (18) |
O12—C42—C43 | 125.19 (18) | Cl12—C84—C83 | 109.81 (18) |
C41—C42—C43 | 119.79 (18) | Cl11—C83—H83A | 110.33 |
C42—C43—C44 | 120.1 (2) | Cl11—C83—H83B | 110.28 |
C43—C44—C45 | 120.5 (2) | C84—C83—H83A | 110.32 |
C44—C45—C46 | 119.9 (2) | C84—C83—H83B | 110.34 |
C41—C46—C45 | 120.24 (19) | H83A—C83—H83B | 108.58 |
O12—C47—C48 | 108.41 (16) | Cl12—C84—H84A | 109.68 |
O13—C48—C47 | 106.81 (16) | Cl12—C84—H84B | 109.66 |
C50—C49—C54 | 119.87 (19) | C83—C84—H84A | 109.74 |
O13—C49—C50 | 114.77 (17) | C83—C84—H84B | 109.71 |
O13—C49—C54 | 125.36 (19) | H84A—C84—H84B | 108.23 |
O14—C50—C51 | 125.23 (19) | Cl1A—C73A—C74A | 113.3 (9) |
C49—C50—C51 | 119.51 (18) | Cl2A—C74A—C73A | 111.7 (9) |
O14—C50—C49 | 115.26 (17) | Cl1A—C73A—H73C | 108.90 |
C50—C51—C52 | 119.9 (2) | Cl1A—C73A—H73D | 108.82 |
C51—C52—C53 | 120.6 (2) | C74A—C73A—H73C | 108.97 |
C52—C53—C54 | 119.9 (2) | C74A—C73A—H73D | 108.90 |
C49—C54—C53 | 120.1 (2) | H73C—C73A—H73D | 107.78 |
O14—C55—C56 | 108.53 (17) | Cl2A—C74A—H74C | 109.30 |
O15—C56—C55 | 107.39 (15) | Cl2A—C74A—H74D | 109.33 |
O15—C57—C58 | 114.81 (18) | C73A—C74A—H74C | 109.29 |
O15—C57—C62 | 125.37 (19) | C73A—C74A—H74D | 109.32 |
C58—C57—C62 | 119.82 (19) | H74C—C74A—H74D | 107.85 |
C57—C58—C59 | 119.82 (19) | Cl5A—C77A—C78A | 104.6 (4) |
O16—C58—C59 | 125.20 (19) | Cl6A—C78A—C77A | 108.9 (4) |
O16—C58—C57 | 114.98 (17) | Cl5A—C77A—H77C | 110.73 |
C58—C59—C60 | 119.8 (2) | Cl5A—C77A—H77D | 110.71 |
C59—C60—C61 | 120.3 (2) | C78A—C77A—H77C | 110.92 |
C60—C61—C62 | 120.6 (2) | C78A—C77A—H77D | 110.93 |
C57—C62—C61 | 119.7 (2) | H77C—C77A—H77D | 108.90 |
O16—C63—C64 | 108.30 (17) | Cl6A—C78A—H78C | 109.84 |
O17—C64—C63 | 107.80 (17) | Cl6A—C78A—H78D | 109.87 |
O17—C65—C66 | 114.88 (18) | C77A—C78A—H78C | 109.93 |
O17—C65—C70 | 125.62 (19) | C77A—C78A—H78D | 109.93 |
C66—C65—C70 | 119.50 (18) | H78C—C78A—H78D | 108.34 |
O18—C66—C67 | 125.70 (19) | Cl8A—C79A—C80A | 106.8 (7) |
C65—C66—C67 | 119.80 (19) | Cl7A—C80A—C79A | 113.2 (7) |
O18—C66—C65 | 114.50 (17) | Cl8A—C79A—H79C | 110.42 |
C66—C67—C68 | 120.0 (2) | Cl8A—C79A—H79D | 110.38 |
C67—C68—C69 | 120.1 (2) | C80A—C79A—H79C | 110.32 |
C68—C69—C70 | 120.4 (2) | C80A—C79A—H79D | 110.37 |
C65—C70—C69 | 120.2 (2) | H79C—C79A—H79D | 108.57 |
O18—C71—C72 | 107.56 (17) | Cl7A—C80A—H80C | 108.84 |
O11—C72—C71 | 106.75 (17) | Cl7A—C80A—H80D | 108.91 |
C42—C43—H43 | 119.97 | C79A—C80A—H80C | 108.98 |
C44—C43—H43 | 119.98 | C79A—C80A—H80D | 109.00 |
C43—C44—H44 | 119.74 | H80C—C80A—H80D | 107.79 |
C32—O1—C1—C2 | 176.46 (19) | C22—C17—C18—C19 | −0.9 (3) |
C1—O1—C32—C31 | 174.15 (18) | O5—C17—C18—O6 | −1.3 (3) |
C32—O1—C1—C6 | −4.4 (3) | C17—C18—C19—C20 | −0.2 (3) |
C7—O2—C2—C1 | −177.95 (19) | O6—C18—C19—C20 | −179.6 (2) |
C7—O2—C2—C3 | 2.3 (3) | C18—C19—C20—C21 | 1.0 (3) |
C2—O2—C7—C8 | −175.11 (18) | C19—C20—C21—C22 | −0.7 (4) |
C8—O3—C9—C14 | 4.9 (3) | C20—C21—C22—C17 | −0.3 (3) |
C8—O3—C9—C10 | −175.13 (18) | O6—C23—C24—O7 | 76.0 (2) |
C9—O3—C8—C7 | −178.52 (17) | C26—C25—C30—C29 | −0.3 (3) |
C15—O4—C10—C9 | 175.41 (18) | O7—C25—C26—O8 | 0.4 (3) |
C15—O4—C10—C11 | −4.8 (3) | O7—C25—C30—C29 | −179.5 (2) |
C10—O4—C15—C16 | 179.31 (17) | C30—C25—C26—O8 | −178.86 (19) |
C16—O5—C17—C22 | −1.9 (3) | C30—C25—C26—C27 | 0.4 (3) |
C17—O5—C16—C15 | 179.96 (17) | O7—C25—C26—C27 | 179.7 (2) |
C16—O5—C17—C18 | 178.01 (18) | C25—C26—C27—C28 | −0.3 (4) |
C23—O6—C18—C19 | 5.5 (3) | O8—C26—C27—C28 | 178.9 (2) |
C18—O6—C23—C24 | −178.72 (17) | C26—C27—C28—C29 | 0.0 (4) |
C23—O6—C18—C17 | −173.90 (18) | C27—C28—C29—C30 | 0.1 (4) |
C24—O7—C25—C30 | 2.4 (3) | C28—C29—C30—C25 | 0.0 (4) |
C25—O7—C24—C23 | −179.10 (17) | O8—C31—C32—O1 | −77.3 (2) |
C24—O7—C25—C26 | −176.81 (18) | C42—C41—C46—C45 | −0.5 (3) |
C31—O8—C26—C27 | −4.4 (3) | C46—C41—C42—C43 | −0.6 (3) |
C31—O8—C26—C25 | 174.84 (18) | O11—C41—C46—C45 | 179.4 (2) |
C26—O8—C31—C32 | 179.68 (17) | O11—C41—C42—O12 | −0.6 (3) |
C41—O11—C72—C71 | −177.49 (17) | O11—C41—C42—C43 | 179.51 (19) |
C72—O11—C41—C46 | 4.7 (3) | C46—C41—C42—O12 | 179.22 (19) |
C72—O11—C41—C42 | −175.44 (18) | C41—C42—C43—C44 | 1.2 (3) |
C47—O12—C42—C41 | −178.80 (17) | O12—C42—C43—C44 | −178.6 (2) |
C42—O12—C47—C48 | 172.20 (17) | C42—C43—C44—C45 | −0.7 (3) |
C47—O12—C42—C43 | 1.0 (3) | C43—C44—C45—C46 | −0.4 (3) |
C48—O13—C49—C54 | −3.9 (3) | C44—C45—C46—C41 | 1.0 (3) |
C49—O13—C48—C47 | 179.82 (16) | O12—C47—C48—O13 | −79.68 (19) |
C48—O13—C49—C50 | 175.72 (17) | O13—C49—C54—C53 | −178.29 (19) |
C55—O14—C50—C51 | 4.0 (3) | C54—C49—C50—O14 | 178.51 (18) |
C55—O14—C50—C49 | −176.73 (17) | O13—C49—C50—O14 | −1.1 (2) |
C50—O14—C55—C56 | −176.43 (16) | O13—C49—C50—C51 | 178.21 (18) |
C56—O15—C57—C58 | −174.93 (18) | C54—C49—C50—C51 | −2.2 (3) |
C57—O15—C56—C55 | 179.16 (17) | C50—C49—C54—C53 | 2.1 (3) |
C56—O15—C57—C62 | 4.7 (3) | C49—C50—C51—C52 | 0.2 (3) |
C63—O16—C58—C57 | 176.97 (18) | O14—C50—C51—C52 | 179.43 (19) |
C58—O16—C63—C64 | 177.67 (17) | C50—C51—C52—C53 | 1.9 (3) |
C63—O16—C58—C59 | −3.3 (3) | C51—C52—C53—C54 | −1.9 (3) |
C65—O17—C64—C63 | 177.83 (17) | C52—C53—C54—C49 | −0.1 (3) |
C64—O17—C65—C70 | −5.6 (3) | O14—C55—C56—O15 | 78.5 (2) |
C64—O17—C65—C66 | 174.69 (17) | C58—C57—C62—C61 | −0.5 (3) |
C71—O18—C66—C67 | 3.6 (3) | O15—C57—C58—O16 | −0.7 (3) |
C71—O18—C66—C65 | −176.56 (17) | C62—C57—C58—O16 | 179.70 (19) |
C66—O18—C71—C72 | −174.92 (17) | O15—C57—C58—C59 | 179.60 (19) |
C2—C1—C6—C5 | 1.2 (4) | O15—C57—C62—C61 | 179.9 (2) |
O1—C1—C6—C5 | −177.9 (2) | C62—C57—C58—C59 | 0.0 (3) |
O1—C1—C2—C3 | 178.7 (2) | C57—C58—C59—C60 | 0.5 (3) |
C6—C1—C2—C3 | −0.5 (3) | O16—C58—C59—C60 | −179.2 (2) |
O1—C1—C2—O2 | −1.0 (3) | C58—C59—C60—C61 | −0.3 (3) |
C6—C1—C2—O2 | 179.7 (2) | C59—C60—C61—C62 | −0.2 (3) |
O2—C2—C3—C4 | 179.1 (2) | C60—C61—C62—C57 | 0.7 (3) |
C1—C2—C3—C4 | −0.6 (3) | O16—C63—C64—O17 | −76.9 (2) |
C2—C3—C4—C5 | 1.0 (4) | C66—C65—C70—C69 | 0.0 (3) |
C3—C4—C5—C6 | −0.2 (4) | O17—C65—C66—O18 | 0.3 (3) |
C4—C5—C6—C1 | −0.9 (4) | O17—C65—C70—C69 | −179.7 (2) |
O2—C7—C8—O3 | 78.0 (2) | O17—C65—C66—C67 | −179.90 (18) |
O3—C9—C10—O4 | 0.8 (3) | C70—C65—C66—C67 | 0.4 (3) |
C14—C9—C10—O4 | −179.25 (19) | C70—C65—C66—O18 | −179.42 (18) |
C10—C9—C14—C13 | −0.6 (3) | O18—C66—C67—C68 | 179.0 (2) |
O3—C9—C10—C11 | −179.1 (2) | C65—C66—C67—C68 | −0.8 (3) |
C14—C9—C10—C11 | 0.9 (3) | C66—C67—C68—C69 | 0.7 (3) |
O3—C9—C14—C13 | 179.4 (2) | C67—C68—C69—C70 | −0.3 (3) |
C9—C10—C11—C12 | −0.3 (3) | C68—C69—C70—C65 | 0.0 (3) |
O4—C10—C11—C12 | 179.9 (2) | O18—C71—C72—O11 | 79.5 (2) |
C10—C11—C12—C13 | −0.7 (4) | Cl1—C73—C74—Cl2 | −66.3 (4) |
C11—C12—C13—C14 | 1.0 (4) | Cl3—C75—C76—Cl4 | −178.8 (3) |
C12—C13—C14—C9 | −0.4 (4) | Cl3A—C75A—C76A—Cl4A | −175.8 (2) |
O4—C15—C16—O5 | −79.5 (2) | Cl5—C77—C78—Cl6 | 179.2 (2) |
O5—C17—C18—C19 | 179.19 (19) | Cl8—C79—C80—Cl7 | 179.28 (14) |
C18—C17—C22—C21 | 1.1 (3) | Cl9—C81—C82—Cl10 | 64.2 (2) |
C22—C17—C18—O6 | 178.59 (19) | Cl11—C83—C84—Cl12 | 178.98 (13) |
O5—C17—C22—C21 | −179.0 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C75—H75A···O8 | 0.99 | 2.44 | 3.302 (6) | 145 |
C75—H75B···O3 | 0.99 | 2.55 | 3.385 (7) | 142 |
C78—H78A···O1 | 0.99 | 2.51 | 3.389 (5) | 147 |
C78—H78B···O6 | 0.99 | 2.46 | 3.310 (4) | 143 |
C80—H80B···O15 | 0.99 | 2.58 | 3.351 (3) | 134 |
C83—H83A···O17 | 0.99 | 2.55 | 3.391 (3) | 142 |
C83—H83B···O14 | 0.99 | 2.57 | 3.404 (3) | 142 |
C3—H3···Cg8 | 0.95 | 2.90 | 3.788 (3) | 155 |
C15—H15A···Cg5i | 0.99 | 2.94 | 3.399 (2) | 109 |
C15—H15B···Cg5i | 0.99 | 3.09 | 3.399 (2) | 99 |
C23—H23A···Cg4ii | 0.99 | 3.24 | 3.354 (2) | 88 |
C23—H23B···Cg4ii | 0.99 | 2.71 | 3.354 (2) | 123 |
C27—H27···Cg1iii | 0.95 | 3.19 | 4.124 (3) | 167 |
C43—H43···Cg6iv | 0.95 | 2.77 | 3.684 (2) | 162 |
C51—H51···Cg7v | 0.95 | 2.76 | 3.679 (2) | 164 |
C59—H59···Cg2 | 0.95 | 3.23 | 4.144 (2) | 162 |
C71—H71B···Cg3vi | 0.99 | 2.76 | 3.458 (2) | 128 |
C77—H77A···Cg1 | 0.99 | 2.90 | 3.611 (5) | 129 |
C77—H77B···Cg3 | 0.99 | 2.83 | 3.605 (6) | 136 |
C79—H79A···Cg5 | 0.99 | 2.92 | 3.682 (3) | 135 |
C79—H79B···Cg7 | 0.99 | 2.85 | 3.639 (3) | 137 |
C84—H84A···Cg8 | 0.99 | 2.82 | 3.575 (3) | 134 |
C84—H84B···Cg6 | 0.99 | 2.92 | 3.690 (3) | 135 |
C78A—H78C···Cg3 | 0.99 | 2.98 | 3.725 (6) | 133 |
C78A—H78D···Cg1 | 0.99 | 2.80 | 3.583 (6) | 136 |
C80A—H80C···Cg7 | 0.99 | 2.86 | 3.641 (11) | 137 |
C80A—H80D···Cg5 | 0.99 | 2.82 | 3.574 (11) | 133 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+2, −z+1; (iii) −x+3, −y+2, −z+1; (iv) −x+4, −y+3, −z; (v) −x+3, −y+3, −z; (vi) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C32H32O8·3C2H4Cl2 |
Mr | 841.43 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 13.478 (2), 14.3841 (18), 21.381 (2) |
α, β, γ (°) | 97.144 (10), 97.854 (10), 103.405 (11) |
V (Å3) | 3941.6 (9) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.49 |
Crystal size (mm) | 0.56 × 0.34 × 0.23 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | ψ-scan (SHELXTL; Bruker, 1997) |
Tmin, Tmax | 0.840, 0.884 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 25644, 18086, 12891 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.044, 0.120, 1.03 |
No. of reflections | 18086 |
No. of parameters | 1027 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.95, −0.76 |
Computer programs: CAD-4-PC (Enraf-Nonius, 1996), CAD-4-PC, XCAD4 (Harms, 1995), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), PLATON (Spek, 2001).
C32—O1—C1—C2 | 176.46 (19) | C58—O16—C63—C64 | 177.67 (17) |
C1—O1—C32—C31 | 174.15 (18) | C65—O17—C64—C63 | 177.83 (17) |
C7—O2—C2—C1 | −177.95 (19) | C64—O17—C65—C66 | 174.69 (17) |
C2—O2—C7—C8 | −175.11 (18) | C71—O18—C66—C65 | −176.56 (17) |
C8—O3—C9—C10 | −175.13 (18) | C66—O18—C71—C72 | −174.92 (17) |
C9—O3—C8—C7 | −178.52 (17) | O1—C1—C2—O2 | −1.0 (3) |
C15—O4—C10—C9 | 175.41 (18) | O2—C7—C8—O3 | 78.0 (2) |
C10—O4—C15—C16 | 179.31 (17) | O3—C9—C10—O4 | 0.8 (3) |
C17—O5—C16—C15 | 179.96 (17) | O4—C15—C16—O5 | −79.5 (2) |
C16—O5—C17—C18 | 178.01 (18) | O5—C17—C18—O6 | −1.3 (3) |
C18—O6—C23—C24 | −178.72 (17) | O6—C23—C24—O7 | 76.0 (2) |
C23—O6—C18—C17 | −173.90 (18) | O7—C25—C26—O8 | 0.4 (3) |
C25—O7—C24—C23 | −179.10 (17) | O8—C31—C32—O1 | −77.3 (2) |
C24—O7—C25—C26 | −176.81 (18) | O11—C41—C42—O12 | −0.6 (3) |
C31—O8—C26—C25 | 174.84 (18) | O12—C47—C48—O13 | −79.68 (19) |
C26—O8—C31—C32 | 179.68 (17) | O13—C49—C50—O14 | −1.1 (2) |
C41—O11—C72—C71 | −177.49 (17) | O14—C55—C56—O15 | 78.5 (2) |
C72—O11—C41—C42 | −175.44 (18) | O15—C57—C58—O16 | −0.7 (3) |
C47—O12—C42—C41 | −178.80 (17) | O16—C63—C64—O17 | −76.9 (2) |
C42—O12—C47—C48 | 172.20 (17) | O17—C65—C66—O18 | 0.3 (3) |
C49—O13—C48—C47 | 179.82 (16) | O18—C71—C72—O11 | 79.5 (2) |
C48—O13—C49—C50 | 175.72 (17) | Cl1—C73—C74—Cl2 | −66.3 (4) |
C55—O14—C50—C49 | −176.73 (17) | Cl3—C75—C76—Cl4 | −178.8 (3) |
C50—O14—C55—C56 | −176.43 (16) | Cl5—C77—C78—Cl6 | 179.2 (2) |
C56—O15—C57—C58 | −174.93 (18) | Cl8—C79—C80—Cl7 | 179.28 (14) |
C57—O15—C56—C55 | 179.16 (17) | Cl9—C81—C82—Cl10 | 64.2 (2) |
C63—O16—C58—C57 | 176.97 (18) | Cl11—C83—C84—Cl12 | 178.98 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C75—H75A···O8 | 0.99 | 2.44 | 3.302 (6) | 145 |
C75—H75B···O3 | 0.99 | 2.55 | 3.385 (7) | 142 |
C78—H78A···O1 | 0.99 | 2.51 | 3.389 (5) | 147 |
C78—H78B···O6 | 0.99 | 2.46 | 3.310 (4) | 143 |
C80—H80B···O15 | 0.99 | 2.58 | 3.351 (3) | 134 |
C83—H83A···O17 | 0.99 | 2.55 | 3.391 (3) | 142 |
C83—H83B···O14 | 0.99 | 2.57 | 3.404 (3) | 142 |
C3—H3···Cg8 | 0.95 | 2.90 | 3.788 (3) | 155 |
C15—H15A···Cg5i | 0.99 | 2.94 | 3.399 (2) | 109 |
C15—H15B···Cg5i | 0.99 | 3.09 | 3.399 (2) | 99 |
C23—H23A···Cg4ii | 0.99 | 3.24 | 3.354 (2) | 88 |
C23—H23B···Cg4ii | 0.99 | 2.71 | 3.354 (2) | 123 |
C27—H27···Cg1iii | 0.95 | 3.19 | 4.124 (3) | 167 |
C43—H43···Cg6iv | 0.95 | 2.77 | 3.684 (2) | 162 |
C51—H51···Cg7v | 0.95 | 2.76 | 3.679 (2) | 164 |
C59—H59···Cg2 | 0.95 | 3.23 | 4.144 (2) | 162 |
C71—H71B···Cg3vi | 0.99 | 2.76 | 3.458 (2) | 128 |
C77—H77A···Cg1 | 0.99 | 2.90 | 3.611 (5) | 129 |
C77—H77B···Cg3 | 0.99 | 2.83 | 3.605 (6) | 136 |
C79—H79A···Cg5 | 0.99 | 2.92 | 3.682 (3) | 135 |
C79—H79B···Cg7 | 0.99 | 2.85 | 3.639 (3) | 137 |
C84—H84A···Cg8 | 0.99 | 2.82 | 3.575 (3) | 134 |
C84—H84B···Cg6 | 0.99 | 2.92 | 3.690 (3) | 135 |
C78A—H78C···Cg3 | 0.99 | 2.98 | 3.725 (6) | 133 |
C78A—H78D···Cg1 | 0.99 | 2.80 | 3.583 (6) | 136 |
C80A—H80C···Cg7 | 0.99 | 2.86 | 3.641 (11) | 137 |
C80A—H80D···Cg5 | 0.99 | 2.82 | 3.574 (11) | 133 |
Symmetry codes: (i) x−1, y, z; (ii) −x+2, −y+2, −z+1; (iii) −x+3, −y+2, −z+1; (iv) −x+4, −y+3, −z; (v) −x+3, −y+3, −z; (vi) x+1, y, z. |
Solvation of a host molecule can inhibit guest complexation if the energy of desolvating the host molecule is sufficiently high (Bryan et al., 2001). Solvation can also alter the host conformation, which could facilitate or inhibit the eventual guest complexation (Sachleben et al., 1997). As part of our continuing studies of tetrabenzo-24-crown-8 (Levitskaia et al., 2000; Bryan et al., 2000), we have determined its structure when solvated by three 1,2-dichloroethane molecules (DCE), to give the title compound, (I).
Two molecules of tetrabenzo-24-crown-8 and six molecules of DCE make up the asymmetric unit of (I). Both crown ether molecules adopt the conformation previously observed when bound to acetonitrile, Cs+ or Rb+ (Bryan et al., 2000, 1999; Levitskaia et al., 2000). Two DCE molecules fill each crown cavity, forming weak C—H···O and C—H···π hydrogen bonds to both the crown O atoms and the arene rings. The geometrical parameters for these interactions, as calculated by PLATON (Spek, 2001), are presented in Table 2, with ring centroids represented as Cg1 (C1—C6), Cg2 (C9—C13) etc.
Polar solvents such as acetonitrile and nitromethane have often been observed to coordinate crown ether host molecules (Sachleben et al., 1997), but, to the best of our knowledge, this is the first report of a crown-ether-DCE complex. All four of the included solvent molecules adopt an anti configuration. Two additional DCE molecules are observed outside the crown; both adopt a gauche conformation and neither appears to engage in hydrogen bonding.
No π-stacking of arene rings is observed in the crystal structure of (I). However, close Carene—H···π contacts, some of which may represent edge-face arene interactions, are clearly present. The geometrical parameters for these interactions, as calculated by PLATON, are also presented in Table 2.