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The title compound, C32H32O8·3C2H4Cl2, illustrates how tetrabenzo-24-crown-8 may be solvated by a common solvent-extraction diluent, 1,2-di­chloro­ethane (DCE). Two mol­ecules of DCE occupy the crown cavity, forming weak hydrogen bonds to the ether O atoms and the crown arene rings, while the crown adopts its most commonly observed binding conformation. The asymmetric unit is composed of two mol­ecules of tetrabenzo-24-crown-8 and six mol­ecules of DCE.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101014627/fr1347sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101014627/fr1347Isup2.hkl
Contains datablock I

CCDC reference: 179287

Comment top

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.

Related literature top

For related literature, see: Brown & Foubister (1983); Bryan et al. (1999, 2000, 2001); Levitskaia et al. (2000); Pedersen (1967); Sachleben et al. (1997); Spek (2001).

Experimental top

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.

Refinement top

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.

Computing details top

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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) showing 50% displacement ellipsoids. H atoms have been omitted for clarity, except those on 1,2-dichloroethane, and only the major disorder components are shown.
2,5,12,15,22,25,32,35-Octaoxopentacyclo[34.4.0.06,11. 016,21.026,31]tetraconta-6,8,10,16,18,20,26,28,30,36,38,40-dodecaene tris(1,2-dichloroethane) solvate top
Crystal data top
C32H32O8·3C2H4Cl2Z = 4
Mr = 841.43F(000) = 1752
Triclinic, P1Dx = 1.418 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 13.478 (2) ÅCell parameters from 25 reflections
b = 14.3841 (18) Åθ = 10.0–14.4°
c = 21.381 (2) ŵ = 0.49 mm1
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
Data collection top
Enraf-Nonius CAD-4
diffractometer
12891 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.025
Graphite monochromatorθmax = 27.5°, θmin = 2.0°
ω scansh = 1717
Absorption correction: ψ-scan
(SHELXTL; Bruker, 1997)
k = 1818
Tmin = 0.840, Tmax = 0.884l = 2027
25644 measured reflections3 standard reflections every 120 min
18086 independent reflections intensity decay: 6%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.044Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120H-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 parametersΔρmax = 0.95 e Å3
0 restraintsΔρmin = 0.76 e Å3
0 constraints
Crystal data top
C32H32O8·3C2H4Cl2γ = 103.405 (11)°
Mr = 841.43V = 3941.6 (9) Å3
Triclinic, P1Z = 4
a = 13.478 (2) ÅMo Kα radiation
b = 14.3841 (18) ŵ = 0.49 mm1
c = 21.381 (2) ÅT = 100 K
α = 97.144 (10)°0.56 × 0.34 × 0.23 mm
β = 97.854 (10)°
Data collection top
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 = 0.8843 standard reflections every 120 min
25644 measured reflections intensity decay: 6%
18086 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0440 restraints
wR(F2) = 0.120H-atom parameters constrained
S = 1.03Δρmax = 0.95 e Å3
18086 reflectionsΔρmin = 0.76 e Å3
1027 parameters
Special details top

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

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
O10.44016 (11)0.09195 (11)0.49109 (7)0.0196 (4)
O20.52622 (11)0.15340 (10)0.39864 (7)0.0179 (4)
O30.43188 (11)0.12168 (11)0.26344 (7)0.0187 (4)
O40.26313 (11)0.16004 (11)0.21696 (7)0.0184 (4)
O50.12365 (11)0.24525 (10)0.28704 (7)0.0171 (4)
O60.03819 (11)0.18540 (10)0.37954 (7)0.0166 (4)
O70.05773 (11)0.01594 (10)0.43608 (7)0.0165 (4)
O80.22775 (11)0.02349 (10)0.48229 (7)0.0197 (4)
C10.50479 (16)0.18322 (16)0.50568 (10)0.0192 (6)
C20.55107 (16)0.21701 (15)0.45477 (10)0.0183 (6)
C30.61637 (17)0.30937 (17)0.46397 (11)0.0254 (7)
C40.6351 (2)0.36853 (18)0.52311 (12)0.0328 (8)
C50.5905 (2)0.33548 (19)0.57286 (12)0.0356 (8)
C60.52556 (18)0.24226 (18)0.56454 (11)0.0273 (7)
C70.57468 (16)0.18429 (16)0.34668 (10)0.0199 (6)
C80.53091 (16)0.10892 (16)0.28821 (10)0.0201 (6)
C90.37602 (16)0.05897 (15)0.21049 (10)0.0180 (6)
C100.28296 (16)0.07956 (15)0.18514 (10)0.0179 (6)
C110.21948 (17)0.01968 (17)0.13192 (11)0.0246 (7)
C120.24815 (19)0.06051 (19)0.10349 (12)0.0310 (8)
C130.33975 (19)0.07967 (18)0.12771 (12)0.0304 (7)
C140.40402 (17)0.02041 (17)0.18133 (11)0.0238 (7)
C150.17348 (16)0.18803 (16)0.19016 (10)0.0191 (6)
C160.16702 (16)0.27612 (15)0.23310 (10)0.0180 (6)
C170.11182 (15)0.31617 (15)0.33175 (10)0.0158 (5)
C180.06595 (15)0.28380 (14)0.38320 (10)0.0153 (6)
C190.05165 (16)0.35017 (15)0.43162 (10)0.0183 (6)
C200.08309 (17)0.44924 (16)0.42934 (11)0.0214 (6)
C210.12666 (17)0.48070 (16)0.37873 (11)0.0222 (6)
C220.14107 (16)0.41449 (15)0.32960 (10)0.0195 (6)
C230.01802 (16)0.14784 (15)0.42687 (10)0.0173 (6)
C240.03746 (15)0.03941 (15)0.41408 (10)0.0171 (6)
C250.05629 (16)0.08002 (14)0.42776 (10)0.0168 (6)
C260.14913 (17)0.10180 (15)0.45275 (10)0.0194 (6)
C270.15451 (19)0.19785 (16)0.44672 (12)0.0267 (7)
C280.0684 (2)0.27133 (16)0.41644 (13)0.0320 (8)
C290.0221 (2)0.25033 (16)0.39236 (12)0.0293 (7)
C300.02863 (18)0.15446 (16)0.39791 (10)0.0221 (6)
C310.32013 (16)0.04311 (16)0.51300 (11)0.0228 (7)
C320.39558 (17)0.05144 (17)0.54165 (10)0.0227 (7)
O110.90683 (11)0.26221 (10)0.19633 (7)0.0162 (4)
O120.99351 (11)0.35766 (10)0.11605 (6)0.0148 (4)
O130.94295 (10)0.52824 (10)0.06966 (7)0.0155 (4)
O140.76390 (10)0.54436 (10)0.02110 (7)0.0154 (4)
O150.56347 (11)0.40120 (10)0.00641 (6)0.0160 (4)
O160.48426 (11)0.32060 (10)0.09467 (6)0.0160 (4)
O170.58037 (11)0.34344 (10)0.22864 (7)0.0171 (4)
O180.75486 (11)0.31350 (10)0.27093 (7)0.0171 (4)
C410.92428 (15)0.20639 (14)0.14455 (9)0.0146 (5)
C420.97273 (15)0.25923 (14)0.10039 (10)0.0142 (5)
C430.99492 (16)0.21039 (15)0.04642 (10)0.0163 (6)
C440.96801 (17)0.10941 (15)0.03477 (10)0.0206 (6)
C450.92015 (17)0.05756 (15)0.07719 (11)0.0220 (6)
C460.89892 (16)0.10654 (15)0.13272 (10)0.0184 (6)
C471.04060 (15)0.41214 (14)0.07128 (10)0.0152 (6)
C481.04408 (15)0.51682 (14)0.09118 (10)0.0159 (6)
C490.92748 (15)0.61883 (14)0.08276 (9)0.0148 (5)
C500.82871 (15)0.62726 (14)0.05655 (9)0.0149 (6)
C510.80382 (16)0.71543 (15)0.06843 (10)0.0181 (6)
C520.87636 (18)0.79480 (15)0.10587 (11)0.0217 (6)
C530.97391 (18)0.78747 (15)0.12980 (11)0.0222 (6)
C540.99980 (17)0.69907 (15)0.11820 (10)0.0195 (6)
C550.66501 (15)0.55172 (15)0.00906 (10)0.0165 (6)
C560.60341 (16)0.45279 (15)0.04182 (9)0.0171 (6)
C570.50315 (15)0.30875 (14)0.01313 (10)0.0152 (6)
C580.45908 (15)0.26466 (14)0.03543 (10)0.0155 (6)
C590.39594 (16)0.17113 (15)0.02100 (10)0.0186 (6)
C600.37687 (17)0.12071 (15)0.04161 (11)0.0215 (6)
C610.42000 (17)0.16368 (16)0.08872 (11)0.0224 (6)
C620.48314 (16)0.25833 (16)0.07500 (10)0.0199 (6)
C630.43720 (16)0.28068 (15)0.14469 (10)0.0173 (6)
C640.47818 (15)0.35112 (15)0.20554 (10)0.0173 (6)
C650.63353 (15)0.40431 (15)0.28301 (9)0.0160 (5)
C660.72995 (15)0.38784 (15)0.30665 (9)0.0160 (6)
C670.79044 (16)0.44533 (16)0.36170 (10)0.0191 (6)
C680.75655 (17)0.52029 (16)0.39336 (10)0.0214 (6)
C690.66262 (18)0.53623 (16)0.37022 (10)0.0223 (7)
C700.60080 (16)0.47836 (15)0.31504 (10)0.0197 (6)
C710.84898 (15)0.28993 (15)0.29459 (10)0.0170 (6)
C720.86514 (16)0.21338 (15)0.24519 (10)0.0162 (6)
Cl30.34033 (5)0.08779 (6)0.34147 (4)0.0466 (2)0.500
Cl3A0.34033 (5)0.08779 (6)0.34147 (4)0.0466 (2)0.500
Cl40.06047 (5)0.01284 (5)0.26817 (3)0.0330 (2)0.500
Cl4A0.06047 (5)0.01284 (5)0.26817 (3)0.0330 (2)0.500
C750.2483 (5)0.0143 (4)0.3309 (3)0.0345 (17)0.500
C75A0.2139 (4)0.0960 (4)0.2931 (2)0.0297 (17)0.500
C760.1581 (4)0.0796 (4)0.2843 (2)0.0279 (17)0.500
C76A0.1891 (4)0.0020 (4)0.3111 (2)0.0291 (17)0.500
Cl10.28376 (8)0.48094 (8)0.17510 (5)0.0267 (3)0.730
Cl20.28612 (7)0.71324 (7)0.18846 (5)0.0395 (3)0.730
C730.3432 (3)0.5700 (3)0.24381 (19)0.0368 (12)0.730
C740.2822 (4)0.6445 (3)0.25201 (19)0.0405 (14)0.730
Cl50.38950 (5)0.34427 (6)0.36654 (3)0.0442 (2)0.530
Cl60.24267 (4)0.23139 (4)0.51683 (3)0.0272 (2)0.530
C770.3411 (4)0.3376 (4)0.4420 (2)0.0282 (14)0.530
C780.2865 (3)0.2346 (3)0.4427 (2)0.0236 (14)0.530
Cl70.76987 (4)0.30031 (4)0.00525 (3)0.0264 (2)0.780
Cl80.62269 (5)0.12900 (5)0.12354 (3)0.0303 (2)0.780
C790.6733 (2)0.1642 (2)0.05273 (15)0.0232 (9)0.780
C800.7213 (2)0.2717 (2)0.06447 (14)0.0213 (8)0.780
Cl90.76092 (6)0.95851 (6)0.25590 (4)0.0522 (3)
Cl100.55863 (6)0.78850 (7)0.27183 (4)0.0537 (3)
C810.7552 (2)0.8331 (2)0.24898 (13)0.0367 (9)
C820.6917 (2)0.7841 (2)0.29333 (13)0.0384 (8)
Cl110.64945 (6)0.56941 (5)0.16473 (3)0.0437 (2)
Cl120.94361 (6)0.52501 (6)0.24176 (4)0.0468 (3)
C830.7546 (2)0.51268 (19)0.17553 (12)0.0405 (9)
C840.8361 (2)0.57782 (18)0.22696 (12)0.0334 (8)
Cl1A0.3059 (3)0.5267 (3)0.1952 (2)0.0589 (16)0.270
Cl2A0.17795 (17)0.66320 (16)0.26609 (10)0.0304 (6)0.270
C73A0.3134 (9)0.6490 (7)0.1892 (6)0.045 (4)0.270
C74A0.3004 (8)0.7049 (10)0.2474 (5)0.043 (4)0.270
Cl5A0.38950 (5)0.34427 (6)0.36654 (3)0.0442 (2)0.470
Cl6A0.24267 (4)0.23139 (4)0.51683 (3)0.0272 (2)0.470
C77A0.3198 (4)0.2572 (4)0.4076 (2)0.0245 (16)0.470
C78A0.3179 (4)0.3129 (4)0.4706 (3)0.0217 (16)0.470
Cl7A0.76987 (4)0.30031 (4)0.00525 (3)0.0264 (2)0.220
Cl8A0.62269 (5)0.12900 (5)0.12354 (3)0.0303 (2)0.220
C79A0.6837 (7)0.2303 (7)0.0971 (5)0.023 (3)0.220
C80A0.7010 (8)0.1988 (7)0.0315 (5)0.019 (3)0.220
H30.648300.332200.429900.0300*
H40.678900.432200.529100.0390*
H50.604000.376300.613200.0430*
H60.495700.219500.599300.0330*
H7A0.650400.192900.357400.0240*
H7B0.561700.247100.338600.0240*
H8A0.577100.117100.256000.0240*
H8B0.523800.043200.299400.0240*
H110.156500.033200.114800.0290*
H120.204200.102000.067300.0370*
H130.359300.133800.107700.0360*
H140.467100.034300.198000.0290*
H15A0.110600.135000.187400.0230*
H15B0.179300.202700.146600.0230*
H16A0.236900.320300.247600.0220*
H16B0.122700.311200.209800.0220*
H190.020600.328500.466300.0220*
H200.074300.495000.462900.0260*
H210.147100.548100.377300.0270*
H220.170900.436700.294700.0230*
H23A0.084500.166600.424200.0210*
H23B0.022700.173900.470200.0210*
H24A0.092200.009200.437100.0210*
H24B0.060300.015100.367700.0210*
H270.216800.213300.463200.0320*
H280.072400.336800.412400.0380*
H290.080400.301100.371900.0350*
H300.091300.140000.381200.0270*
H31A0.350100.079700.481500.0270*
H31B0.304200.082600.546800.0270*
H32A0.359700.095900.562900.0270*
H32B0.450300.041100.574000.0270*
H431.028600.245600.017200.0200*
H440.982800.076100.002700.0250*
H450.901600.011200.068800.0260*
H460.867000.070800.162300.0220*
H47A0.999800.388500.027700.0180*
H47B1.111600.404400.070800.0180*
H48A1.062700.534800.138300.0190*
H48B1.096200.558700.071500.0190*
H510.737400.721700.051000.0220*
H520.858300.854500.115000.0260*
H531.023600.842500.154200.0270*
H541.067100.694000.134700.0230*
H55A0.674100.596400.040700.0200*
H55B0.628200.577500.023300.0200*
H56A0.545900.457900.074200.0210*
H56B0.648000.418300.063500.0210*
H590.365700.141300.053500.0220*
H600.333900.056500.051500.0260*
H610.406900.128900.131000.0270*
H620.512100.287900.107900.0240*
H63A0.453800.218100.149500.0210*
H63B0.361000.269100.134300.0210*
H64A0.480300.417800.197600.0210*
H64B0.432900.335900.237600.0210*
H670.855000.433900.378000.0230*
H680.798500.560200.430900.0260*
H690.639700.587000.392000.0270*
H700.536000.489800.299400.0240*
H71A0.844000.265400.335600.0200*
H71B0.907800.348200.301900.0200*
H72A0.913900.178900.264600.0190*
H72B0.798600.165700.226900.0190*
H75A0.227000.005400.372000.0420*0.500
H75B0.278300.044500.313400.0420*0.500
H75C0.217400.107200.247000.0360*0.500
H75D0.160400.149900.302400.0360*0.500
H76A0.128800.137900.302500.0330*0.500
H76B0.181100.100800.244000.0330*0.500
H76C0.239900.051300.298900.0350*0.500
H76D0.190800.011400.357800.0350*0.500
H73A0.347300.538400.282300.0440*0.730
H73B0.414600.602000.239100.0440*0.730
H74A0.310900.688400.293200.0490*0.730
H74B0.209400.611800.253200.0490*0.730
H77A0.399400.360400.478300.0340*0.530
H77B0.292800.379500.446100.0340*0.530
H78A0.334400.192300.438300.0280*0.530
H78B0.227200.211900.406900.0280*0.530
H79A0.725800.128900.043300.0280*0.780
H79B0.616500.147200.015400.0280*0.780
H80A0.778000.289400.101800.0260*0.780
H80B0.668900.307500.073000.0260*0.780
H81A0.725300.801500.204400.0440*
H81B0.826400.824800.258300.0440*
H82A0.719100.817000.337900.0460*
H82B0.695600.715900.290500.0460*
H83A0.730800.448400.188200.0490*
H83B0.782300.503900.135200.0490*
H84A0.807100.587700.266700.0400*
H84B0.859800.641700.213700.0400*
H73C0.381500.678600.178300.0530*0.270
H73D0.259200.652100.153800.0530*0.270
H74C0.311100.773800.242100.0520*0.270
H74D0.353500.701000.283200.0520*0.270
H77C0.248700.228100.383800.0300*0.470
H77D0.355400.205000.413000.0300*0.470
H78C0.285800.367100.464300.0260*0.470
H78D0.389400.340200.494200.0260*0.470
H79C0.640300.277200.096300.0280*0.220
H79D0.750600.261700.125600.0280*0.220
H80C0.633200.167500.003900.0230*0.220
H80D0.741900.149900.033100.0230*0.220
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0194 (7)0.0221 (8)0.0184 (7)0.0049 (6)0.0040 (6)0.0077 (6)
O20.0181 (7)0.0180 (7)0.0167 (7)0.0015 (6)0.0024 (6)0.0060 (6)
O30.0154 (7)0.0224 (8)0.0182 (7)0.0068 (6)0.0006 (6)0.0027 (6)
O40.0159 (7)0.0232 (8)0.0170 (7)0.0085 (6)0.0013 (6)0.0014 (6)
O50.0198 (7)0.0178 (7)0.0161 (7)0.0071 (6)0.0059 (6)0.0043 (6)
O60.0219 (7)0.0154 (7)0.0152 (7)0.0072 (6)0.0055 (6)0.0058 (6)
O70.0154 (7)0.0134 (7)0.0212 (7)0.0046 (5)0.0004 (6)0.0055 (6)
O80.0172 (7)0.0176 (7)0.0280 (8)0.0081 (6)0.0046 (6)0.0095 (6)
C10.0160 (10)0.0215 (11)0.0213 (11)0.0077 (8)0.0013 (8)0.0070 (8)
C20.0148 (9)0.0211 (11)0.0187 (10)0.0062 (8)0.0037 (8)0.0061 (8)
C30.0216 (11)0.0245 (12)0.0265 (12)0.0022 (9)0.0044 (9)0.0073 (9)
C40.0314 (13)0.0243 (12)0.0334 (14)0.0017 (10)0.0081 (11)0.0016 (10)
C50.0398 (15)0.0343 (14)0.0253 (13)0.0072 (11)0.0081 (11)0.0042 (11)
C60.0271 (12)0.0329 (13)0.0216 (11)0.0104 (10)0.0019 (9)0.0049 (10)
C70.0150 (10)0.0241 (11)0.0205 (11)0.0016 (8)0.0019 (8)0.0105 (9)
C80.0155 (10)0.0265 (11)0.0206 (11)0.0077 (8)0.0033 (8)0.0080 (9)
C90.0154 (10)0.0226 (11)0.0161 (10)0.0033 (8)0.0043 (8)0.0050 (8)
C100.0151 (10)0.0225 (11)0.0175 (10)0.0053 (8)0.0061 (8)0.0041 (8)
C110.0186 (11)0.0321 (13)0.0224 (11)0.0086 (9)0.0025 (9)0.0008 (9)
C120.0240 (12)0.0347 (14)0.0292 (13)0.0071 (10)0.0006 (10)0.0088 (10)
C130.0285 (12)0.0295 (13)0.0325 (13)0.0117 (10)0.0053 (10)0.0059 (10)
C140.0205 (11)0.0275 (12)0.0251 (11)0.0097 (9)0.0044 (9)0.0033 (9)
C150.0135 (9)0.0295 (12)0.0162 (10)0.0094 (8)0.0009 (8)0.0049 (9)
C160.0172 (10)0.0238 (11)0.0148 (10)0.0069 (8)0.0033 (8)0.0064 (8)
C170.0135 (9)0.0200 (10)0.0152 (9)0.0083 (8)0.0000 (8)0.0033 (8)
C180.0135 (9)0.0160 (10)0.0176 (10)0.0070 (8)0.0012 (8)0.0054 (8)
C190.0190 (10)0.0221 (11)0.0161 (10)0.0089 (8)0.0020 (8)0.0053 (8)
C200.0234 (11)0.0202 (11)0.0214 (11)0.0102 (9)0.0019 (9)0.0002 (9)
C210.0216 (11)0.0152 (10)0.0306 (12)0.0061 (8)0.0035 (9)0.0051 (9)
C220.0177 (10)0.0202 (11)0.0230 (11)0.0067 (8)0.0043 (8)0.0075 (9)
C230.0183 (10)0.0207 (10)0.0167 (10)0.0082 (8)0.0058 (8)0.0084 (8)
C240.0140 (9)0.0203 (10)0.0179 (10)0.0052 (8)0.0012 (8)0.0060 (8)
C250.0226 (10)0.0130 (9)0.0163 (10)0.0039 (8)0.0073 (8)0.0050 (8)
C260.0246 (11)0.0166 (10)0.0202 (10)0.0061 (8)0.0101 (9)0.0067 (8)
C270.0329 (13)0.0211 (11)0.0346 (13)0.0128 (10)0.0191 (11)0.0109 (10)
C280.0469 (15)0.0135 (11)0.0428 (15)0.0098 (10)0.0261 (12)0.0073 (10)
C290.0367 (14)0.0165 (11)0.0305 (13)0.0022 (10)0.0117 (11)0.0012 (9)
C300.0258 (11)0.0199 (11)0.0182 (10)0.0008 (9)0.0045 (9)0.0029 (8)
C310.0198 (11)0.0251 (11)0.0307 (12)0.0117 (9)0.0080 (9)0.0164 (10)
C320.0213 (11)0.0325 (12)0.0201 (11)0.0120 (9)0.0059 (9)0.0142 (9)
O110.0216 (7)0.0148 (7)0.0159 (7)0.0071 (6)0.0078 (6)0.0072 (6)
O120.0208 (7)0.0118 (7)0.0140 (7)0.0054 (5)0.0054 (6)0.0048 (5)
O130.0154 (7)0.0113 (7)0.0205 (7)0.0051 (5)0.0008 (6)0.0039 (6)
O140.0139 (7)0.0129 (7)0.0198 (7)0.0049 (5)0.0004 (6)0.0046 (6)
O150.0170 (7)0.0151 (7)0.0142 (7)0.0017 (6)0.0006 (6)0.0031 (5)
O160.0170 (7)0.0167 (7)0.0129 (7)0.0021 (6)0.0009 (5)0.0034 (5)
O170.0133 (7)0.0216 (8)0.0164 (7)0.0069 (6)0.0000 (6)0.0016 (6)
O180.0138 (7)0.0233 (8)0.0147 (7)0.0077 (6)0.0001 (5)0.0017 (6)
C410.0140 (9)0.0169 (10)0.0156 (9)0.0078 (8)0.0027 (8)0.0050 (8)
C420.0148 (9)0.0130 (9)0.0172 (10)0.0070 (7)0.0012 (8)0.0062 (8)
C430.0184 (10)0.0164 (10)0.0184 (10)0.0090 (8)0.0047 (8)0.0084 (8)
C440.0277 (11)0.0171 (10)0.0205 (11)0.0123 (9)0.0053 (9)0.0021 (8)
C450.0266 (11)0.0124 (10)0.0298 (12)0.0083 (8)0.0070 (9)0.0051 (9)
C460.0198 (10)0.0155 (10)0.0228 (11)0.0061 (8)0.0054 (8)0.0091 (8)
C470.0146 (9)0.0162 (10)0.0176 (10)0.0049 (8)0.0057 (8)0.0082 (8)
C480.0133 (9)0.0150 (10)0.0198 (10)0.0036 (7)0.0004 (8)0.0074 (8)
C490.0188 (10)0.0126 (9)0.0144 (9)0.0045 (8)0.0033 (8)0.0060 (7)
C500.0183 (10)0.0127 (9)0.0155 (10)0.0036 (8)0.0063 (8)0.0062 (7)
C510.0209 (10)0.0168 (10)0.0212 (10)0.0086 (8)0.0075 (8)0.0087 (8)
C520.0323 (12)0.0116 (10)0.0250 (11)0.0080 (9)0.0110 (9)0.0064 (8)
C530.0290 (12)0.0124 (10)0.0218 (11)0.0001 (8)0.0028 (9)0.0012 (8)
C540.0223 (11)0.0162 (10)0.0186 (10)0.0034 (8)0.0003 (8)0.0042 (8)
C550.0164 (10)0.0179 (10)0.0178 (10)0.0071 (8)0.0019 (8)0.0083 (8)
C560.0184 (10)0.0198 (10)0.0134 (9)0.0047 (8)0.0005 (8)0.0063 (8)
C570.0124 (9)0.0157 (10)0.0180 (10)0.0055 (7)0.0009 (8)0.0047 (8)
C580.0134 (9)0.0167 (10)0.0173 (10)0.0078 (8)0.0010 (8)0.0028 (8)
C590.0167 (10)0.0165 (10)0.0226 (11)0.0049 (8)0.0007 (8)0.0049 (8)
C600.0215 (11)0.0138 (10)0.0264 (11)0.0041 (8)0.0015 (9)0.0006 (8)
C610.0230 (11)0.0218 (11)0.0198 (11)0.0081 (9)0.0034 (9)0.0028 (9)
C620.0206 (10)0.0218 (11)0.0182 (10)0.0065 (8)0.0021 (8)0.0055 (8)
C630.0144 (9)0.0206 (10)0.0167 (10)0.0030 (8)0.0023 (8)0.0059 (8)
C640.0122 (9)0.0230 (11)0.0173 (10)0.0062 (8)0.0012 (8)0.0039 (8)
C650.0157 (9)0.0186 (10)0.0132 (9)0.0022 (8)0.0022 (8)0.0050 (8)
C660.0163 (10)0.0182 (10)0.0143 (9)0.0030 (8)0.0058 (8)0.0053 (8)
C670.0162 (10)0.0249 (11)0.0162 (10)0.0033 (8)0.0022 (8)0.0075 (8)
C680.0244 (11)0.0214 (11)0.0139 (10)0.0010 (9)0.0015 (8)0.0008 (8)
C690.0281 (12)0.0193 (11)0.0198 (11)0.0068 (9)0.0062 (9)0.0004 (8)
C700.0182 (10)0.0222 (11)0.0210 (11)0.0079 (8)0.0045 (8)0.0054 (9)
C710.0137 (9)0.0234 (11)0.0158 (10)0.0069 (8)0.0018 (8)0.0075 (8)
C720.0167 (10)0.0182 (10)0.0169 (10)0.0061 (8)0.0044 (8)0.0104 (8)
Cl30.0301 (3)0.0678 (5)0.0416 (4)0.0044 (3)0.0039 (3)0.0251 (4)
Cl3A0.0301 (3)0.0678 (5)0.0416 (4)0.0044 (3)0.0039 (3)0.0251 (4)
Cl40.0436 (4)0.0313 (3)0.0273 (3)0.0138 (3)0.0102 (3)0.0037 (2)
Cl4A0.0436 (4)0.0313 (3)0.0273 (3)0.0138 (3)0.0102 (3)0.0037 (2)
C750.034 (3)0.039 (3)0.025 (3)0.005 (3)0.005 (2)0.012 (2)
C75A0.030 (3)0.031 (3)0.025 (3)0.002 (2)0.003 (2)0.006 (2)
C760.029 (3)0.028 (3)0.024 (3)0.004 (2)0.000 (2)0.005 (2)
C76A0.037 (3)0.025 (3)0.021 (3)0.002 (2)0.010 (2)0.001 (2)
Cl10.0280 (4)0.0262 (5)0.0273 (5)0.0072 (4)0.0035 (4)0.0108 (4)
Cl20.0392 (5)0.0351 (5)0.0438 (5)0.0082 (4)0.0013 (4)0.0138 (4)
C730.038 (2)0.036 (2)0.030 (2)0.0077 (16)0.0100 (16)0.0013 (17)
C740.058 (3)0.035 (2)0.030 (2)0.014 (2)0.0025 (18)0.0120 (18)
Cl50.0288 (3)0.0839 (6)0.0280 (3)0.0206 (3)0.0081 (3)0.0237 (3)
Cl60.0253 (3)0.0265 (3)0.0305 (3)0.0063 (2)0.0043 (2)0.0088 (2)
C770.024 (2)0.041 (3)0.022 (2)0.007 (2)0.007 (2)0.013 (2)
C780.019 (2)0.031 (3)0.021 (2)0.0125 (18)0.0014 (18)0.0009 (19)
Cl70.0219 (3)0.0202 (3)0.0365 (3)0.0054 (2)0.0003 (2)0.0076 (2)
Cl80.0317 (3)0.0395 (3)0.0246 (3)0.0154 (3)0.0075 (2)0.0081 (2)
C790.0246 (16)0.0244 (17)0.0218 (16)0.0080 (13)0.0042 (13)0.0041 (13)
C800.0194 (13)0.0215 (15)0.0231 (14)0.0092 (11)0.0010 (12)0.0009 (12)
Cl90.0498 (4)0.0427 (4)0.0533 (5)0.0052 (3)0.0073 (4)0.0174 (3)
Cl100.0307 (4)0.0814 (6)0.0438 (4)0.0013 (4)0.0081 (3)0.0186 (4)
C810.0286 (13)0.0491 (17)0.0324 (14)0.0068 (12)0.0047 (11)0.0132 (12)
C820.0332 (14)0.0465 (16)0.0343 (14)0.0040 (12)0.0077 (12)0.0112 (12)
Cl110.0427 (4)0.0490 (4)0.0280 (3)0.0105 (3)0.0053 (3)0.0172 (3)
Cl120.0640 (5)0.0486 (4)0.0491 (4)0.0332 (4)0.0311 (4)0.0284 (3)
C830.066 (2)0.0259 (13)0.0241 (13)0.0040 (13)0.0123 (13)0.0079 (10)
C840.0475 (16)0.0274 (13)0.0278 (13)0.0097 (11)0.0107 (12)0.0088 (10)
Cl1A0.070 (3)0.045 (2)0.083 (3)0.032 (2)0.039 (2)0.029 (2)
Cl2A0.0296 (11)0.0309 (11)0.0267 (10)0.0012 (9)0.0001 (8)0.0116 (9)
C73A0.060 (7)0.023 (5)0.064 (7)0.029 (5)0.014 (6)0.019 (5)
C74A0.038 (6)0.052 (7)0.039 (6)0.002 (5)0.004 (5)0.025 (6)
Cl5A0.0288 (3)0.0839 (6)0.0280 (3)0.0206 (3)0.0081 (3)0.0237 (3)
Cl6A0.0253 (3)0.0265 (3)0.0305 (3)0.0063 (2)0.0043 (2)0.0088 (2)
C77A0.020 (2)0.030 (3)0.025 (3)0.010 (2)0.001 (2)0.006 (2)
C78A0.019 (2)0.022 (3)0.024 (3)0.0060 (19)0.003 (2)0.003 (2)
Cl7A0.0219 (3)0.0202 (3)0.0365 (3)0.0054 (2)0.0003 (2)0.0076 (2)
Cl8A0.0317 (3)0.0395 (3)0.0246 (3)0.0154 (3)0.0075 (2)0.0081 (2)
C79A0.012 (4)0.020 (5)0.035 (6)0.004 (4)0.002 (4)0.001 (5)
C80A0.019 (5)0.013 (5)0.027 (6)0.005 (4)0.001 (4)0.009 (5)
Geometric parameters (Å, º) top
Cl3—C751.816 (7)C32—H32A0.9902
Cl3A—C75A1.839 (5)C41—C421.419 (3)
Cl4—C761.821 (6)C41—C461.379 (3)
Cl4A—C76A1.810 (5)C42—C431.380 (3)
Cl1—C731.782 (4)C43—C441.394 (3)
Cl2—C741.777 (4)C44—C451.378 (3)
Cl5—C771.826 (5)C45—C461.402 (3)
Cl6—C781.768 (4)C47—C481.501 (3)
Cl7—C801.765 (3)C49—C501.410 (3)
Cl8—C791.824 (3)C49—C541.384 (3)
Cl9—C811.774 (3)C50—C511.388 (3)
Cl10—C821.807 (3)C51—C521.393 (3)
Cl11—C831.795 (3)C52—C531.377 (3)
Cl12—C841.795 (3)C53—C541.397 (3)
Cl1A—C73A1.760 (11)C55—C561.500 (3)
Cl2A—C74A1.739 (12)C57—C581.411 (3)
Cl5A—C77A1.782 (5)C57—C621.386 (3)
Cl6A—C78A1.841 (6)C58—C591.387 (3)
Cl7A—C80A1.862 (10)C59—C601.401 (3)
Cl8A—C79A1.702 (10)C60—C611.372 (3)
O1—C321.429 (3)C61—C621.400 (3)
O1—C11.369 (3)C63—C641.497 (3)
O2—C71.430 (3)C65—C661.412 (3)
O2—C21.365 (3)C65—C701.385 (3)
O3—C91.364 (3)C66—C671.385 (3)
O3—C81.428 (3)C67—C681.400 (3)
O4—C151.430 (3)C68—C691.375 (3)
O4—C101.368 (3)C69—C701.394 (3)
O5—C171.362 (3)C71—C721.503 (3)
O5—C161.435 (3)C43—H430.9500
O6—C231.430 (3)C44—H440.9506
O6—C181.367 (2)C45—H450.9497
O7—C251.365 (2)C46—H460.9498
O7—C241.434 (3)C47—H47A0.9903
O8—C261.370 (3)C47—H47B0.9900
O8—C311.431 (3)C48—H48A0.9904
O11—C721.435 (3)C48—H48B0.9905
O11—C411.365 (2)C51—H510.9503
O12—C421.367 (2)C52—H520.9503
O12—C471.434 (2)C53—H530.9504
O13—C491.368 (2)C54—H540.9498
O13—C481.431 (3)C55—H55B0.9888
O14—C551.432 (3)C55—H55A0.9899
O14—C501.368 (2)C56—H56A0.9889
O15—C561.436 (2)C56—H56B0.9896
O15—C571.368 (2)C59—H590.9506
O16—C631.430 (3)C60—H600.9503
O16—C581.367 (2)C61—H610.9495
O17—C641.432 (3)C62—H620.9490
O17—C651.364 (2)C63—H63B0.9905
O18—C711.431 (3)C63—H63A0.9905
O18—C661.369 (3)C64—H64B0.9899
C1—C21.410 (3)C64—H64A0.9893
C1—C61.382 (3)C67—H670.9504
C2—C31.387 (3)C68—H680.9510
C3—C41.390 (3)C69—H690.9513
C4—C51.374 (4)C70—H700.9498
C5—C61.396 (4)C71—H71A0.9899
C7—C81.500 (3)C71—H71B0.9904
C9—C141.386 (3)C72—H72A0.9889
C9—C101.407 (3)C72—H72B0.9899
C10—C111.385 (3)C75—C761.503 (8)
C11—C121.395 (4)C75A—C76A1.484 (8)
C12—C131.374 (4)C75—H75A0.9898
C13—C141.391 (3)C75—H75B0.9901
C15—C161.497 (3)C75A—H75D0.9894
C17—C181.410 (3)C75A—H75C0.9882
C17—C221.386 (3)C76—H76A0.9901
C18—C191.384 (3)C76—H76B0.9915
C19—C201.398 (3)C76A—H76D0.9892
C20—C211.376 (3)C76A—H76C0.9898
C21—C221.393 (3)C73—C741.502 (7)
C23—C241.504 (3)C73—H73A0.9895
C25—C261.411 (3)C73—H73B0.9903
C25—C301.388 (3)C74—H74B0.9902
C26—C271.391 (3)C74—H74A0.9896
C27—C281.392 (4)C77—C781.497 (7)
C28—C291.372 (4)C77—H77A0.9889
C29—C301.394 (3)C77—H77B0.9895
C31—C321.497 (3)C78—H78B0.9904
C3—H30.9504C78—H78A0.9901
C4—H40.9503C79—C801.506 (4)
C5—H50.9505C79—H79A0.9896
C6—H60.9501C79—H79B0.9902
C7—H7A0.9899C80—H80B0.9888
C7—H7B0.9902C80—H80A0.9892
C8—H8B0.9902C81—C821.496 (4)
C8—H8A0.9895C81—H81A0.9899
C11—H110.9496C81—H81B0.9908
C12—H120.9496C82—H82B0.9893
C13—H130.9496C82—H82A0.9895
C14—H140.9505C83—C841.493 (4)
C15—H15B0.9896C83—H83A0.9898
C15—H15A0.9894C83—H83B0.9908
C16—H16A0.9903C84—H84A0.9907
C16—H16B0.9902C84—H84B0.9900
C19—H190.9507C73A—C74A1.450 (17)
C20—H200.9508C73A—H73C0.9899
C21—H210.9500C73A—H73D0.9904
C22—H220.9499C74A—H74D0.9904
C23—H23A0.9904C74A—H74C0.9909
C23—H23B0.9896C77A—C78A1.486 (8)
C24—H24B0.9904C77A—H77C0.9901
C24—H24A0.9895C77A—H77D0.9904
C27—H270.9505C78A—H78D0.9899
C28—H280.9496C78A—H78C0.9898
C29—H290.9501C79A—C80A1.486 (15)
C30—H300.9497C79A—H79C0.9903
C31—H31B0.9894C79A—H79D0.9904
C31—H31A0.9892C80A—H80C0.9908
C32—H32B0.9907C80A—H80D0.9902
C1—O1—C32117.65 (16)C45—C44—H44119.77
C2—O2—C7116.70 (16)C44—C45—H45120.03
C8—O3—C9117.42 (17)C46—C45—H45120.10
C10—O4—C15117.01 (16)C45—C46—H46119.86
C16—O5—C17116.51 (16)C41—C46—H46119.90
C18—O6—C23117.08 (16)O12—C47—H47A110.00
C24—O7—C25116.46 (16)H47A—C47—H47B108.42
C26—O8—C31116.94 (16)C48—C47—H47B109.98
C41—O11—C72117.41 (16)O12—C47—H47B110.04
C42—O12—C47115.75 (15)C48—C47—H47A109.99
C48—O13—C49117.27 (15)C47—C48—H48A110.31
C50—O14—C55116.67 (16)O13—C48—H48B110.33
C56—O15—C57117.40 (15)C47—C48—H48B110.39
C58—O16—C63116.89 (16)H48A—C48—H48B108.62
C64—O17—C65117.37 (16)O13—C48—H48A110.37
C66—O18—C71116.95 (16)C50—C51—H51120.04
O1—C1—C6125.3 (2)C52—C51—H51120.02
C2—C1—C6119.6 (2)C51—C52—H52119.69
O1—C1—C2115.01 (18)C53—C52—H52119.72
C1—C2—C3119.8 (2)C54—C53—H53120.02
O2—C2—C1115.35 (19)C52—C53—H53120.04
O2—C2—C3124.86 (19)C49—C54—H54119.96
C2—C3—C4119.9 (2)C53—C54—H54119.96
C3—C4—C5120.3 (2)H55A—C55—H55B108.38
C4—C5—C6120.4 (2)O14—C55—H55A109.99
C1—C6—C5119.9 (2)O14—C55—H55B109.99
O2—C7—C8108.71 (18)C56—C55—H55A109.97
O3—C8—C7107.00 (18)C56—C55—H55B109.99
O3—C9—C14125.4 (2)O15—C56—H56B110.17
C10—C9—C14119.6 (2)C55—C56—H56A110.25
O3—C9—C10115.00 (19)O15—C56—H56A110.21
C9—C10—C11119.8 (2)C55—C56—H56B110.26
O4—C10—C9115.01 (18)H56A—C56—H56B108.56
O4—C10—C11125.2 (2)C58—C59—H59120.11
C10—C11—C12119.9 (2)C60—C59—H59120.08
C11—C12—C13120.2 (2)C61—C60—H60119.87
C12—C13—C14120.5 (2)C59—C60—H60119.88
C9—C14—C13120.0 (2)C60—C61—H61119.71
O4—C15—C16107.44 (17)C62—C61—H61119.71
O5—C16—C15108.06 (17)C61—C62—H62120.17
C18—C17—C22119.65 (19)C57—C62—H62120.12
O5—C17—C22124.92 (19)C64—C63—H63A109.99
O5—C17—C18115.43 (18)O16—C63—H63B110.04
O6—C18—C17114.51 (18)C64—C63—H63B110.05
O6—C18—C19125.50 (19)H63A—C63—H63B108.41
C17—C18—C19119.99 (19)O16—C63—H63A110.05
C18—C19—C20119.7 (2)O17—C64—H64A110.11
C19—C20—C21120.2 (2)O17—C64—H64B110.15
C20—C21—C22120.5 (2)C63—C64—H64A110.19
C17—C22—C21119.9 (2)C63—C64—H64B110.14
O6—C23—C24107.41 (17)H64A—C64—H64B108.45
O7—C24—C23107.54 (17)C68—C67—H67120.00
C26—C25—C30119.74 (19)C66—C67—H67119.97
O7—C25—C30124.8 (2)C67—C68—H68119.98
O7—C25—C26115.49 (18)C69—C68—H68119.97
O8—C26—C25115.27 (18)C70—C69—H69119.83
O8—C26—C27125.3 (2)C68—C69—H69119.80
C25—C26—C27119.4 (2)C69—C70—H70119.84
C26—C27—C28119.8 (2)C65—C70—H70119.92
C27—C28—C29120.8 (2)O18—C71—H71B110.16
C28—C29—C30120.0 (2)C72—C71—H71A110.19
C25—C30—C29120.2 (2)O18—C71—H71A110.17
O8—C31—C32108.33 (18)C72—C71—H71B110.19
O1—C32—C31107.78 (17)H71A—C71—H71B108.56
C4—C3—H3120.02H72A—C72—H72B108.64
C2—C3—H3120.07C71—C72—H72A110.39
C5—C4—H4119.87C71—C72—H72B110.33
C3—C4—H4119.79O11—C72—H72A110.36
C6—C5—H5119.82O11—C72—H72B110.37
C4—C5—H5119.79Cl3—C75—C76104.1 (4)
C1—C6—H6120.10Cl3A—C75A—C76A106.1 (3)
C5—C6—H6120.00Cl4—C76—C75108.5 (4)
O2—C7—H7B109.97Cl4A—C76A—C75A106.4 (4)
H7A—C7—H7B108.35Cl3—C75—H75A110.91
O2—C7—H7A109.91Cl3—C75—H75B110.96
C8—C7—H7A109.94C76—C75—H75A110.90
C8—C7—H7B109.97C76—C75—H75B110.97
C7—C8—H8B110.37H75A—C75—H75B108.93
O3—C8—H8B110.35Cl3A—C75A—H75C110.54
O3—C8—H8A110.36Cl3A—C75A—H75D110.47
H8A—C8—H8B108.47C76A—C75A—H75C110.52
C7—C8—H8A110.30C76A—C75A—H75D110.49
C10—C11—H11120.02H75C—C75A—H75D108.67
C12—C11—H11120.05Cl4—C76—H76A110.07
C13—C12—H12119.90Cl4—C76—H76B109.95
C11—C12—H12119.91C75—C76—H76A110.05
C12—C13—H13119.74C75—C76—H76B110.02
C14—C13—H13119.78H76A—C76—H76B108.27
C9—C14—H14119.98Cl4A—C76A—H76C110.51
C13—C14—H14120.06Cl4A—C76A—H76D110.50
O4—C15—H15B110.25H76C—C76A—H76D108.66
C16—C15—H15A110.20Cl1—C73—C74110.5 (3)
C16—C15—H15B110.21Cl2—C74—C73111.1 (3)
O4—C15—H15A110.21Cl1—C73—H73A109.54
H15A—C15—H15B108.53Cl1—C73—H73B109.57
H16A—C16—H16B108.38C74—C73—H73A109.54
O5—C16—H16A110.16C74—C73—H73B109.56
C15—C16—H16B110.11H73A—C73—H73B108.05
C15—C16—H16A110.05Cl2—C74—H74A109.41
O5—C16—H16B110.08Cl2—C74—H74B109.45
C20—C19—H19120.15C73—C74—H74A109.49
C18—C19—H19120.13C73—C74—H74B109.42
C19—C20—H20119.85H74A—C74—H74B107.96
C21—C20—H20119.91Cl5—C77—C78108.5 (3)
C20—C21—H21119.72Cl6—C78—C77106.9 (3)
C22—C21—H21119.77Cl5—C77—H77A109.90
C17—C22—H22120.06Cl5—C77—H77B109.94
C21—C22—H22120.06C78—C77—H77A110.07
H23A—C23—H23B108.48C78—C77—H77B110.07
C24—C23—H23B110.23H77A—C77—H77B108.36
C24—C23—H23A110.25Cl6—C78—H78A110.29
O6—C23—H23A110.26Cl6—C78—H78B110.32
O6—C23—H23B110.21C77—C78—H78A110.37
C23—C24—H24A110.21C77—C78—H78B110.31
C23—C24—H24B110.17H78A—C78—H78B108.65
H24A—C24—H24B108.52Cl8—C79—C80109.3 (2)
O7—C24—H24A110.18Cl7—C80—C79106.9 (2)
O7—C24—H24B110.22Cl8—C79—H79A109.76
C26—C27—H27120.11Cl8—C79—H79B109.78
C28—C27—H27120.07C80—C79—H79A109.90
C27—C28—H28119.56C80—C79—H79B109.78
C29—C28—H28119.60H79A—C79—H79B108.26
C30—C29—H29119.91Cl7—C80—H80A110.30
C28—C29—H29120.07Cl7—C80—H80B110.36
C25—C30—H30119.90C79—C80—H80A110.35
C29—C30—H30119.95C79—C80—H80B110.36
H31A—C31—H31B108.31H80A—C80—H80B108.57
O8—C31—H31A110.05Cl9—C81—C82112.6 (2)
C32—C31—H31B110.06Cl10—C82—C81109.56 (19)
C32—C31—H31A110.03Cl9—C81—H81A109.11
O8—C31—H31B110.06Cl9—C81—H81B109.10
O1—C32—H32B110.17C82—C81—H81A109.07
C31—C32—H32A110.12C82—C81—H81B109.09
C31—C32—H32B110.13H81A—C81—H81B107.77
H32A—C32—H32B108.44Cl10—C82—H82A109.70
O1—C32—H32A110.20Cl10—C82—H82B109.75
O11—C41—C46125.79 (18)C81—C82—H82A109.73
C42—C41—C46119.54 (18)C81—C82—H82B109.73
O11—C41—C42114.67 (17)H82A—C82—H82B108.35
O12—C42—C41115.02 (17)Cl11—C83—C84106.99 (18)
O12—C42—C43125.19 (18)Cl12—C84—C83109.81 (18)
C41—C42—C43119.79 (18)Cl11—C83—H83A110.33
C42—C43—C44120.1 (2)Cl11—C83—H83B110.28
C43—C44—C45120.5 (2)C84—C83—H83A110.32
C44—C45—C46119.9 (2)C84—C83—H83B110.34
C41—C46—C45120.24 (19)H83A—C83—H83B108.58
O12—C47—C48108.41 (16)Cl12—C84—H84A109.68
O13—C48—C47106.81 (16)Cl12—C84—H84B109.66
C50—C49—C54119.87 (19)C83—C84—H84A109.74
O13—C49—C50114.77 (17)C83—C84—H84B109.71
O13—C49—C54125.36 (19)H84A—C84—H84B108.23
O14—C50—C51125.23 (19)Cl1A—C73A—C74A113.3 (9)
C49—C50—C51119.51 (18)Cl2A—C74A—C73A111.7 (9)
O14—C50—C49115.26 (17)Cl1A—C73A—H73C108.90
C50—C51—C52119.9 (2)Cl1A—C73A—H73D108.82
C51—C52—C53120.6 (2)C74A—C73A—H73C108.97
C52—C53—C54119.9 (2)C74A—C73A—H73D108.90
C49—C54—C53120.1 (2)H73C—C73A—H73D107.78
O14—C55—C56108.53 (17)Cl2A—C74A—H74C109.30
O15—C56—C55107.39 (15)Cl2A—C74A—H74D109.33
O15—C57—C58114.81 (18)C73A—C74A—H74C109.29
O15—C57—C62125.37 (19)C73A—C74A—H74D109.32
C58—C57—C62119.82 (19)H74C—C74A—H74D107.85
C57—C58—C59119.82 (19)Cl5A—C77A—C78A104.6 (4)
O16—C58—C59125.20 (19)Cl6A—C78A—C77A108.9 (4)
O16—C58—C57114.98 (17)Cl5A—C77A—H77C110.73
C58—C59—C60119.8 (2)Cl5A—C77A—H77D110.71
C59—C60—C61120.3 (2)C78A—C77A—H77C110.92
C60—C61—C62120.6 (2)C78A—C77A—H77D110.93
C57—C62—C61119.7 (2)H77C—C77A—H77D108.90
O16—C63—C64108.30 (17)Cl6A—C78A—H78C109.84
O17—C64—C63107.80 (17)Cl6A—C78A—H78D109.87
O17—C65—C66114.88 (18)C77A—C78A—H78C109.93
O17—C65—C70125.62 (19)C77A—C78A—H78D109.93
C66—C65—C70119.50 (18)H78C—C78A—H78D108.34
O18—C66—C67125.70 (19)Cl8A—C79A—C80A106.8 (7)
C65—C66—C67119.80 (19)Cl7A—C80A—C79A113.2 (7)
O18—C66—C65114.50 (17)Cl8A—C79A—H79C110.42
C66—C67—C68120.0 (2)Cl8A—C79A—H79D110.38
C67—C68—C69120.1 (2)C80A—C79A—H79C110.32
C68—C69—C70120.4 (2)C80A—C79A—H79D110.37
C65—C70—C69120.2 (2)H79C—C79A—H79D108.57
O18—C71—C72107.56 (17)Cl7A—C80A—H80C108.84
O11—C72—C71106.75 (17)Cl7A—C80A—H80D108.91
C42—C43—H43119.97C79A—C80A—H80C108.98
C44—C43—H43119.98C79A—C80A—H80D109.00
C43—C44—H44119.74H80C—C80A—H80D107.79
C32—O1—C1—C2176.46 (19)C22—C17—C18—C190.9 (3)
C1—O1—C32—C31174.15 (18)O5—C17—C18—O61.3 (3)
C32—O1—C1—C64.4 (3)C17—C18—C19—C200.2 (3)
C7—O2—C2—C1177.95 (19)O6—C18—C19—C20179.6 (2)
C7—O2—C2—C32.3 (3)C18—C19—C20—C211.0 (3)
C2—O2—C7—C8175.11 (18)C19—C20—C21—C220.7 (4)
C8—O3—C9—C144.9 (3)C20—C21—C22—C170.3 (3)
C8—O3—C9—C10175.13 (18)O6—C23—C24—O776.0 (2)
C9—O3—C8—C7178.52 (17)C26—C25—C30—C290.3 (3)
C15—O4—C10—C9175.41 (18)O7—C25—C26—O80.4 (3)
C15—O4—C10—C114.8 (3)O7—C25—C30—C29179.5 (2)
C10—O4—C15—C16179.31 (17)C30—C25—C26—O8178.86 (19)
C16—O5—C17—C221.9 (3)C30—C25—C26—C270.4 (3)
C17—O5—C16—C15179.96 (17)O7—C25—C26—C27179.7 (2)
C16—O5—C17—C18178.01 (18)C25—C26—C27—C280.3 (4)
C23—O6—C18—C195.5 (3)O8—C26—C27—C28178.9 (2)
C18—O6—C23—C24178.72 (17)C26—C27—C28—C290.0 (4)
C23—O6—C18—C17173.90 (18)C27—C28—C29—C300.1 (4)
C24—O7—C25—C302.4 (3)C28—C29—C30—C250.0 (4)
C25—O7—C24—C23179.10 (17)O8—C31—C32—O177.3 (2)
C24—O7—C25—C26176.81 (18)C42—C41—C46—C450.5 (3)
C31—O8—C26—C274.4 (3)C46—C41—C42—C430.6 (3)
C31—O8—C26—C25174.84 (18)O11—C41—C46—C45179.4 (2)
C26—O8—C31—C32179.68 (17)O11—C41—C42—O120.6 (3)
C41—O11—C72—C71177.49 (17)O11—C41—C42—C43179.51 (19)
C72—O11—C41—C464.7 (3)C46—C41—C42—O12179.22 (19)
C72—O11—C41—C42175.44 (18)C41—C42—C43—C441.2 (3)
C47—O12—C42—C41178.80 (17)O12—C42—C43—C44178.6 (2)
C42—O12—C47—C48172.20 (17)C42—C43—C44—C450.7 (3)
C47—O12—C42—C431.0 (3)C43—C44—C45—C460.4 (3)
C48—O13—C49—C543.9 (3)C44—C45—C46—C411.0 (3)
C49—O13—C48—C47179.82 (16)O12—C47—C48—O1379.68 (19)
C48—O13—C49—C50175.72 (17)O13—C49—C54—C53178.29 (19)
C55—O14—C50—C514.0 (3)C54—C49—C50—O14178.51 (18)
C55—O14—C50—C49176.73 (17)O13—C49—C50—O141.1 (2)
C50—O14—C55—C56176.43 (16)O13—C49—C50—C51178.21 (18)
C56—O15—C57—C58174.93 (18)C54—C49—C50—C512.2 (3)
C57—O15—C56—C55179.16 (17)C50—C49—C54—C532.1 (3)
C56—O15—C57—C624.7 (3)C49—C50—C51—C520.2 (3)
C63—O16—C58—C57176.97 (18)O14—C50—C51—C52179.43 (19)
C58—O16—C63—C64177.67 (17)C50—C51—C52—C531.9 (3)
C63—O16—C58—C593.3 (3)C51—C52—C53—C541.9 (3)
C65—O17—C64—C63177.83 (17)C52—C53—C54—C490.1 (3)
C64—O17—C65—C705.6 (3)O14—C55—C56—O1578.5 (2)
C64—O17—C65—C66174.69 (17)C58—C57—C62—C610.5 (3)
C71—O18—C66—C673.6 (3)O15—C57—C58—O160.7 (3)
C71—O18—C66—C65176.56 (17)C62—C57—C58—O16179.70 (19)
C66—O18—C71—C72174.92 (17)O15—C57—C58—C59179.60 (19)
C2—C1—C6—C51.2 (4)O15—C57—C62—C61179.9 (2)
O1—C1—C6—C5177.9 (2)C62—C57—C58—C590.0 (3)
O1—C1—C2—C3178.7 (2)C57—C58—C59—C600.5 (3)
C6—C1—C2—C30.5 (3)O16—C58—C59—C60179.2 (2)
O1—C1—C2—O21.0 (3)C58—C59—C60—C610.3 (3)
C6—C1—C2—O2179.7 (2)C59—C60—C61—C620.2 (3)
O2—C2—C3—C4179.1 (2)C60—C61—C62—C570.7 (3)
C1—C2—C3—C40.6 (3)O16—C63—C64—O1776.9 (2)
C2—C3—C4—C51.0 (4)C66—C65—C70—C690.0 (3)
C3—C4—C5—C60.2 (4)O17—C65—C66—O180.3 (3)
C4—C5—C6—C10.9 (4)O17—C65—C70—C69179.7 (2)
O2—C7—C8—O378.0 (2)O17—C65—C66—C67179.90 (18)
O3—C9—C10—O40.8 (3)C70—C65—C66—C670.4 (3)
C14—C9—C10—O4179.25 (19)C70—C65—C66—O18179.42 (18)
C10—C9—C14—C130.6 (3)O18—C66—C67—C68179.0 (2)
O3—C9—C10—C11179.1 (2)C65—C66—C67—C680.8 (3)
C14—C9—C10—C110.9 (3)C66—C67—C68—C690.7 (3)
O3—C9—C14—C13179.4 (2)C67—C68—C69—C700.3 (3)
C9—C10—C11—C120.3 (3)C68—C69—C70—C650.0 (3)
O4—C10—C11—C12179.9 (2)O18—C71—C72—O1179.5 (2)
C10—C11—C12—C130.7 (4)Cl1—C73—C74—Cl266.3 (4)
C11—C12—C13—C141.0 (4)Cl3—C75—C76—Cl4178.8 (3)
C12—C13—C14—C90.4 (4)Cl3A—C75A—C76A—Cl4A175.8 (2)
O4—C15—C16—O579.5 (2)Cl5—C77—C78—Cl6179.2 (2)
O5—C17—C18—C19179.19 (19)Cl8—C79—C80—Cl7179.28 (14)
C18—C17—C22—C211.1 (3)Cl9—C81—C82—Cl1064.2 (2)
C22—C17—C18—O6178.59 (19)Cl11—C83—C84—Cl12178.98 (13)
O5—C17—C22—C21179.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C75—H75A···O80.992.443.302 (6)145
C75—H75B···O30.992.553.385 (7)142
C78—H78A···O10.992.513.389 (5)147
C78—H78B···O60.992.463.310 (4)143
C80—H80B···O150.992.583.351 (3)134
C83—H83A···O170.992.553.391 (3)142
C83—H83B···O140.992.573.404 (3)142
C3—H3···Cg80.952.903.788 (3)155
C15—H15A···Cg5i0.992.943.399 (2)109
C15—H15B···Cg5i0.993.093.399 (2)99
C23—H23A···Cg4ii0.993.243.354 (2)88
C23—H23B···Cg4ii0.992.713.354 (2)123
C27—H27···Cg1iii0.953.194.124 (3)167
C43—H43···Cg6iv0.952.773.684 (2)162
C51—H51···Cg7v0.952.763.679 (2)164
C59—H59···Cg20.953.234.144 (2)162
C71—H71B···Cg3vi0.992.763.458 (2)128
C77—H77A···Cg10.992.903.611 (5)129
C77—H77B···Cg30.992.833.605 (6)136
C79—H79A···Cg50.992.923.682 (3)135
C79—H79B···Cg70.992.853.639 (3)137
C84—H84A···Cg80.992.823.575 (3)134
C84—H84B···Cg60.992.923.690 (3)135
C78A—H78C···Cg30.992.983.725 (6)133
C78A—H78D···Cg10.992.803.583 (6)136
C80A—H80C···Cg70.992.863.641 (11)137
C80A—H80D···Cg50.992.823.574 (11)133
Symmetry codes: (i) x1, 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 formulaC32H32O8·3C2H4Cl2
Mr841.43
Crystal system, space groupTriclinic, 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)
V3)3941.6 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.49
Crystal size (mm)0.56 × 0.34 × 0.23
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ-scan
(SHELXTL; Bruker, 1997)
Tmin, Tmax0.840, 0.884
No. of measured, independent and
observed [I > 2σ(I)] reflections
25644, 18086, 12891
Rint0.025
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.044, 0.120, 1.03
No. of reflections18086
No. of parameters1027
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)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).

Selected torsion angles (º) top
C32—O1—C1—C2176.46 (19)C58—O16—C63—C64177.67 (17)
C1—O1—C32—C31174.15 (18)C65—O17—C64—C63177.83 (17)
C7—O2—C2—C1177.95 (19)C64—O17—C65—C66174.69 (17)
C2—O2—C7—C8175.11 (18)C71—O18—C66—C65176.56 (17)
C8—O3—C9—C10175.13 (18)C66—O18—C71—C72174.92 (17)
C9—O3—C8—C7178.52 (17)O1—C1—C2—O21.0 (3)
C15—O4—C10—C9175.41 (18)O2—C7—C8—O378.0 (2)
C10—O4—C15—C16179.31 (17)O3—C9—C10—O40.8 (3)
C17—O5—C16—C15179.96 (17)O4—C15—C16—O579.5 (2)
C16—O5—C17—C18178.01 (18)O5—C17—C18—O61.3 (3)
C18—O6—C23—C24178.72 (17)O6—C23—C24—O776.0 (2)
C23—O6—C18—C17173.90 (18)O7—C25—C26—O80.4 (3)
C25—O7—C24—C23179.10 (17)O8—C31—C32—O177.3 (2)
C24—O7—C25—C26176.81 (18)O11—C41—C42—O120.6 (3)
C31—O8—C26—C25174.84 (18)O12—C47—C48—O1379.68 (19)
C26—O8—C31—C32179.68 (17)O13—C49—C50—O141.1 (2)
C41—O11—C72—C71177.49 (17)O14—C55—C56—O1578.5 (2)
C72—O11—C41—C42175.44 (18)O15—C57—C58—O160.7 (3)
C47—O12—C42—C41178.80 (17)O16—C63—C64—O1776.9 (2)
C42—O12—C47—C48172.20 (17)O17—C65—C66—O180.3 (3)
C49—O13—C48—C47179.82 (16)O18—C71—C72—O1179.5 (2)
C48—O13—C49—C50175.72 (17)Cl1—C73—C74—Cl266.3 (4)
C55—O14—C50—C49176.73 (17)Cl3—C75—C76—Cl4178.8 (3)
C50—O14—C55—C56176.43 (16)Cl5—C77—C78—Cl6179.2 (2)
C56—O15—C57—C58174.93 (18)Cl8—C79—C80—Cl7179.28 (14)
C57—O15—C56—C55179.16 (17)Cl9—C81—C82—Cl1064.2 (2)
C63—O16—C58—C57176.97 (18)Cl11—C83—C84—Cl12178.98 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C75—H75A···O80.992.443.302 (6)145
C75—H75B···O30.992.553.385 (7)142
C78—H78A···O10.992.513.389 (5)147
C78—H78B···O60.992.463.310 (4)143
C80—H80B···O150.992.583.351 (3)134
C83—H83A···O170.992.553.391 (3)142
C83—H83B···O140.992.573.404 (3)142
C3—H3···Cg80.952.903.788 (3)155
C15—H15A···Cg5i0.992.943.399 (2)109
C15—H15B···Cg5i0.993.093.399 (2)99
C23—H23A···Cg4ii0.993.243.354 (2)88
C23—H23B···Cg4ii0.992.713.354 (2)123
C27—H27···Cg1iii0.953.194.124 (3)167
C43—H43···Cg6iv0.952.773.684 (2)162
C51—H51···Cg7v0.952.763.679 (2)164
C59—H59···Cg20.953.234.144 (2)162
C71—H71B···Cg3vi0.992.763.458 (2)128
C77—H77A···Cg10.992.903.611 (5)129
C77—H77B···Cg30.992.833.605 (6)136
C79—H79A···Cg50.992.923.682 (3)135
C79—H79B···Cg70.992.853.639 (3)137
C84—H84A···Cg80.992.823.575 (3)134
C84—H84B···Cg60.992.923.690 (3)135
C78A—H78C···Cg30.992.983.725 (6)133
C78A—H78D···Cg10.992.803.583 (6)136
C80A—H80C···Cg70.992.863.641 (11)137
C80A—H80D···Cg50.992.823.574 (11)133
Symmetry codes: (i) x1, 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.
 

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