Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103004542/jz1549sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270103004542/jz1549IIsup2.hkl |
CCDC reference: 214171
Compound (I) was synthesized via diboronation of bis(p-tolyl)acetylene with B2Cl4 according to the literature method of Siebert et al. (1989). Compound (I) (950 mg, 2.57 mmol) was dissolved in toluene (20 ml), and this solution was refluxed for 4 h. The solvent was removed in a vacuum to yield a red-brown oily residue. Recrystallization from pentane afforded yellowish crystals of (II) at room temperature, which were completely insoluble in common organic solvents once formed.
There are five dichloromethane molecules in the structure, and two of them are strongly disordered. As it was not possible to model these disordered molecules, we used the SQUEEZE option in PLATON (Spek, 2003). H atoms were inserted at calculated positions, and a common isotropic temperature factor was refined for each type. Residual electron density of about 1 e Å−3 was observed around the solvent molecules.
Data collection: SMART (Bruker, 1997/98); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXL97.
Fig. 1. The molecular structure of (II). H atoms and solvent molecules have been omitted for clarity, and displacement ellipsoids are shown at the 30% probability level. |
C64H56B8Cl6O5·5(CH2Cl2) | Z = 2 |
Mr = 1628.90 | F(000) = 1664 |
Triclinic, P1 | Dx = 1.334 Mg m−3 |
a = 13.7073 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.5780 (9) Å | Cell parameters from 6409 reflections |
c = 20.0237 (11) Å | θ = 2.3–31.1° |
α = 68.135 (1)° | µ = 0.59 mm−1 |
β = 82.695 (1)° | T = 190 K |
γ = 73.925 (1)° | Irregular, yellow |
V = 4056.3 (4) Å3 | 0.45 × 0.32 × 0.31 mm |
CCD area detector diffractometer | 25625 independent reflections |
Radiation source: fine-focus sealed tube | 17850 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ω–scan | θmax = 31.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | h = −19→19 |
Tmin = 0.896, Tmax = 1.000 | k = −21→24 |
68074 measured reflections | l = 0→29 |
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)] = 0.063 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.214 | Only H-atom displacement parameters refined |
S = 1.17 | w = 1/[σ2(Fo2) + (0.1264P)2] where P = (Fo2 + 2Fc2)/3 |
25625 reflections | (Δ/σ)max = 0.009 |
841 parameters | Δρmax = 1.06 e Å−3 |
0 restraints | Δρmin = −1.34 e Å−3 |
C64H56B8Cl6O5·5(CH2Cl2) | γ = 73.925 (1)° |
Mr = 1628.90 | V = 4056.3 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.7073 (8) Å | Mo Kα radiation |
b = 16.5780 (9) Å | µ = 0.59 mm−1 |
c = 20.0237 (11) Å | T = 190 K |
α = 68.135 (1)° | 0.45 × 0.32 × 0.31 mm |
β = 82.695 (1)° |
CCD area detector diffractometer | 25625 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1999) | 17850 reflections with I > 2σ(I) |
Tmin = 0.896, Tmax = 1.000 | Rint = 0.034 |
68074 measured reflections |
R[F2 > 2σ(F2)] = 0.063 | 0 restraints |
wR(F2) = 0.214 | Only H-atom displacement parameters refined |
S = 1.17 | Δρmax = 1.06 e Å−3 |
25625 reflections | Δρmin = −1.34 e Å−3 |
841 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.31285 (4) | 0.85585 (3) | 0.33018 (3) | 0.02855 (11) | |
Cl2 | 0.46936 (4) | 0.61044 (4) | 0.13147 (3) | 0.03401 (12) | |
Cl3 | 0.26846 (4) | 0.56737 (3) | 0.18956 (3) | 0.03167 (12) | |
Cl4 | 0.22802 (4) | 0.54846 (3) | 0.38654 (3) | 0.03095 (11) | |
Cl5 | 0.05870 (3) | 0.81519 (3) | 0.18713 (2) | 0.02506 (10) | |
Cl6 | 0.08033 (5) | 0.89154 (4) | 0.41656 (3) | 0.03937 (14) | |
Cl7 | 0.27779 (12) | 0.30328 (9) | 0.14477 (10) | 0.1172 (5) | |
Cl8 | 0.06686 (12) | 0.38298 (10) | 0.16773 (9) | 0.1126 (5) | |
Cl9 | 0.49553 (10) | 0.32663 (12) | 0.22218 (14) | 0.1459 (8) | |
Cl10 | 0.69698 (11) | 0.31809 (14) | 0.25728 (8) | 0.1275 (6) | |
Cl11 | 0.1859 (3) | 0.9499 (2) | 0.54780 (15) | 0.2224 (15) | |
Cl12 | 0.3703 (3) | 0.9905 (3) | 0.5006 (4) | 0.397 (4) | |
O1 | 0.23996 (11) | 0.89955 (9) | 0.07741 (7) | 0.0251 (3) | |
O2 | 0.29697 (10) | 0.74199 (8) | 0.14407 (7) | 0.0214 (2) | |
O3 | 0.25621 (10) | 0.84872 (8) | 0.20489 (7) | 0.0209 (2) | |
O4 | 0.22214 (10) | 0.70389 (8) | 0.26872 (7) | 0.0209 (2) | |
O5 | 0.13440 (10) | 0.83013 (9) | 0.30358 (7) | 0.0231 (3) | |
B1 | 0.22115 (16) | 0.91892 (14) | 0.13846 (11) | 0.0221 (4) | |
B2 | 0.26843 (16) | 0.81386 (14) | 0.07772 (11) | 0.0229 (4) | |
B3 | 0.29955 (16) | 0.75180 (13) | 0.21513 (11) | 0.0216 (4) | |
B4 | 0.21402 (16) | 0.88479 (14) | 0.26699 (11) | 0.0222 (4) | |
B5 | 0.33070 (17) | 0.65099 (14) | 0.12497 (12) | 0.0247 (4) | |
B6 | 0.28288 (16) | 0.62560 (14) | 0.31929 (11) | 0.0227 (4) | |
B7 | 0.11458 (15) | 0.75932 (14) | 0.27676 (11) | 0.0213 (4) | |
B8 | 0.07933 (18) | 0.82327 (15) | 0.36934 (12) | 0.0265 (4) | |
C1 | 0.16759 (15) | 1.00599 (12) | 0.15161 (10) | 0.0226 (3) | |
C2 | 0.16406 (15) | 0.98814 (12) | 0.22393 (10) | 0.0228 (3) | |
C3 | 0.12614 (15) | 1.09259 (12) | 0.09421 (10) | 0.0236 (3) | |
C4 | 0.07739 (17) | 1.09415 (14) | 0.03687 (11) | 0.0313 (4) | |
H4 | 0.0715 | 1.0395 | 0.0346 | 0.0469 (14)* | |
C5 | 0.0372 (2) | 1.17458 (17) | −0.01693 (12) | 0.0390 (5) | |
H5 | 0.0028 | 1.1741 | −0.0550 | 0.0469 (14)* | |
C6 | 0.04594 (18) | 1.25597 (15) | −0.01675 (11) | 0.0350 (5) | |
C7 | 0.0951 (2) | 1.25429 (14) | 0.04024 (13) | 0.0378 (5) | |
H7 | 0.1019 | 1.3090 | 0.0418 | 0.0469 (14)* | |
C8 | 0.13449 (19) | 1.17433 (14) | 0.09520 (12) | 0.0339 (4) | |
H8 | 0.1674 | 1.1752 | 0.1338 | 0.0469 (14)* | |
C9 | 0.0046 (2) | 1.34253 (18) | −0.07728 (14) | 0.0491 (7) | |
H9A | 0.0578 | 1.3549 | −0.1145 | 0.106 (3)* | |
H9B | −0.0175 | 1.3918 | −0.0586 | 0.106 (3)* | |
H9C | −0.0533 | 1.3371 | −0.0980 | 0.106 (3)* | |
C10 | 0.11240 (16) | 1.05286 (13) | 0.25945 (10) | 0.0258 (4) | |
C11 | 0.16342 (19) | 1.07187 (15) | 0.30580 (12) | 0.0350 (5) | |
H11 | 0.2339 | 1.0449 | 0.3132 | 0.0469 (14)* | |
C12 | 0.1121 (2) | 1.12975 (17) | 0.34106 (14) | 0.0444 (6) | |
H12 | 0.1482 | 1.1424 | 0.3720 | 0.0469 (14)* | |
C13 | 0.0088 (2) | 1.16969 (17) | 0.33209 (14) | 0.0443 (6) | |
C14 | −0.0405 (2) | 1.15155 (19) | 0.28519 (14) | 0.0460 (6) | |
H14 | −0.1110 | 1.1784 | 0.2779 | 0.0469 (14)* | |
C15 | 0.01058 (18) | 1.09526 (16) | 0.24874 (12) | 0.0349 (5) | |
H15 | −0.0249 | 1.0855 | 0.2158 | 0.0469 (14)* | |
C16 | −0.0464 (3) | 1.2307 (3) | 0.3720 (2) | 0.0737 (11) | |
H16A | −0.0321 | 1.2007 | 0.4234 | 0.106 (3)* | |
H16B | −0.1196 | 1.2449 | 0.3654 | 0.106 (3)* | |
H16C | −0.0235 | 1.2863 | 0.3534 | 0.106 (3)* | |
C17 | 0.27146 (15) | 0.78013 (13) | 0.01578 (10) | 0.0252 (4) | |
C18 | 0.29573 (15) | 0.68872 (13) | 0.04375 (10) | 0.0249 (4) | |
C19 | 0.25240 (16) | 0.83969 (13) | −0.05993 (10) | 0.0273 (4) | |
C20 | 0.17543 (17) | 0.91854 (15) | −0.07790 (12) | 0.0320 (4) | |
H20 | 0.1335 | 0.9344 | −0.0408 | 0.0469 (14)* | |
C21 | 0.1589 (2) | 0.97423 (16) | −0.14880 (13) | 0.0387 (5) | |
H21 | 0.1044 | 1.0267 | −0.1596 | 0.0469 (14)* | |
C22 | 0.2198 (2) | 0.95552 (17) | −0.20441 (12) | 0.0409 (5) | |
C23 | 0.2971 (2) | 0.87750 (19) | −0.18669 (13) | 0.0506 (7) | |
H23 | 0.3399 | 0.8628 | −0.2239 | 0.0469 (14)* | |
C24 | 0.3134 (2) | 0.82036 (17) | −0.11593 (12) | 0.0431 (6) | |
H24 | 0.3670 | 0.7672 | −0.1054 | 0.0469 (14)* | |
C25 | 0.2012 (3) | 1.0179 (2) | −0.28141 (15) | 0.0608 (8) | |
H25A | 0.1482 | 1.0720 | −0.2824 | 0.106 (3)* | |
H25B | 0.1793 | 0.9875 | −0.3083 | 0.106 (3)* | |
H25C | 0.2641 | 1.0348 | −0.3035 | 0.106 (3)* | |
C26 | 0.28945 (16) | 0.62788 (14) | 0.00668 (11) | 0.0268 (4) | |
C27 | 0.35783 (17) | 0.54364 (15) | 0.02021 (12) | 0.0323 (4) | |
H27 | 0.4129 | 0.5262 | 0.0512 | 0.0469 (14)* | |
C28 | 0.34564 (19) | 0.48539 (16) | −0.01143 (13) | 0.0366 (5) | |
H28 | 0.3937 | 0.4291 | −0.0025 | 0.0469 (14)* | |
C29 | 0.26532 (19) | 0.50754 (17) | −0.05550 (13) | 0.0386 (5) | |
C30 | 0.19646 (19) | 0.59103 (18) | −0.06862 (14) | 0.0400 (5) | |
H30 | 0.1404 | 0.6070 | −0.0984 | 0.0469 (14)* | |
C31 | 0.20822 (18) | 0.65133 (17) | −0.03893 (13) | 0.0352 (5) | |
H31 | 0.1613 | 0.7084 | −0.0495 | 0.0469 (14)* | |
C32 | 0.2514 (2) | 0.4432 (2) | −0.08865 (19) | 0.0549 (7) | |
H32A | 0.3061 | 0.4367 | −0.1243 | 0.106 (3)* | |
H32B | 0.1857 | 0.4667 | −0.1122 | 0.106 (3)* | |
H32C | 0.2533 | 0.3846 | −0.0509 | 0.106 (3)* | |
C33 | 0.39488 (14) | 0.62503 (12) | 0.30861 (10) | 0.0231 (3) | |
C34 | 0.40524 (14) | 0.70177 (12) | 0.25368 (10) | 0.0229 (3) | |
C35 | 0.47490 (14) | 0.55343 (13) | 0.35515 (10) | 0.0255 (4) | |
C36 | 0.49254 (19) | 0.46527 (15) | 0.35797 (13) | 0.0365 (5) | |
H36 | 0.4527 | 0.4513 | 0.3302 | 0.0469 (14)* | |
C37 | 0.5680 (2) | 0.39751 (16) | 0.40113 (14) | 0.0428 (6) | |
H37 | 0.5803 | 0.3381 | 0.4014 | 0.0469 (14)* | |
C38 | 0.62566 (18) | 0.41537 (17) | 0.44367 (12) | 0.0400 (5) | |
C39 | 0.60668 (17) | 0.50232 (17) | 0.44207 (12) | 0.0361 (5) | |
H39 | 0.6446 | 0.5156 | 0.4715 | 0.0469 (14)* | |
C40 | 0.53265 (16) | 0.57096 (15) | 0.39797 (11) | 0.0304 (4) | |
H40 | 0.5215 | 0.6305 | 0.3972 | 0.0469 (14)* | |
C41 | 0.7068 (2) | 0.3412 (2) | 0.49058 (16) | 0.0585 (8) | |
H41A | 0.7683 | 0.3624 | 0.4860 | 0.106 (3)* | |
H41B | 0.7224 | 0.2892 | 0.4754 | 0.106 (3)* | |
H41C | 0.6825 | 0.3240 | 0.5409 | 0.106 (3)* | |
C42 | 0.49931 (15) | 0.73220 (13) | 0.22695 (10) | 0.0252 (4) | |
C43 | 0.49644 (18) | 0.82287 (16) | 0.19829 (16) | 0.0426 (6) | |
H43 | 0.4328 | 0.8658 | 0.1934 | 0.0469 (14)* | |
C44 | 0.5850 (2) | 0.85217 (19) | 0.1766 (2) | 0.0646 (10) | |
H44 | 0.5811 | 0.9147 | 0.1587 | 0.0469 (14)* | |
C45 | 0.6787 (2) | 0.7915 (2) | 0.1806 (2) | 0.0561 (8) | |
C46 | 0.68159 (17) | 0.70144 (17) | 0.20507 (13) | 0.0361 (5) | |
H46 | 0.7446 | 0.6591 | 0.2053 | 0.0469 (14)* | |
C47 | 0.59404 (15) | 0.67156 (14) | 0.22941 (11) | 0.0286 (4) | |
H47 | 0.5985 | 0.6090 | 0.2480 | 0.0469 (14)* | |
C48 | 0.7762 (3) | 0.8213 (3) | 0.1591 (3) | 0.0964 (17) | |
H48A | 0.7732 | 0.8620 | 0.1088 | 0.106 (3)* | |
H48B | 0.8335 | 0.7688 | 0.1646 | 0.106 (3)* | |
H48C | 0.7852 | 0.8526 | 0.1901 | 0.106 (3)* | |
C49 | 0.02081 (15) | 0.75057 (13) | 0.38952 (10) | 0.0253 (4) | |
C50 | 0.03738 (14) | 0.71459 (12) | 0.33654 (10) | 0.0238 (3) | |
C51 | −0.04306 (15) | 0.72811 (14) | 0.45598 (10) | 0.0267 (4) | |
C52 | −0.02273 (18) | 0.64059 (15) | 0.50646 (12) | 0.0338 (4) | |
H52 | 0.0328 | 0.5957 | 0.4984 | 0.0469 (14)* | |
C53 | −0.0837 (2) | 0.61926 (18) | 0.56840 (12) | 0.0392 (5) | |
H53 | −0.0699 | 0.5595 | 0.6020 | 0.0469 (14)* | |
C54 | −0.1640 (2) | 0.68332 (19) | 0.58192 (12) | 0.0423 (6) | |
C55 | −0.1835 (2) | 0.77005 (18) | 0.53211 (13) | 0.0412 (5) | |
H55 | −0.2387 | 0.8147 | 0.5407 | 0.0469 (14)* | |
C56 | −0.12348 (18) | 0.79277 (15) | 0.46963 (12) | 0.0343 (4) | |
H56 | −0.1377 | 0.8527 | 0.4363 | 0.0469 (14)* | |
C57 | −0.2302 (3) | 0.6599 (3) | 0.64950 (16) | 0.0694 (10) | |
H57A | −0.3003 | 0.6706 | 0.6362 | 0.106 (3)* | |
H57B | −0.2282 | 0.6973 | 0.6771 | 0.106 (3)* | |
H57C | −0.2050 | 0.5965 | 0.6789 | 0.106 (3)* | |
C58 | −0.01619 (15) | 0.65329 (13) | 0.32784 (10) | 0.0252 (4) | |
C59 | 0.02246 (15) | 0.60802 (13) | 0.28011 (10) | 0.0264 (4) | |
H59 | 0.0835 | 0.6171 | 0.2535 | 0.0469 (14)* | |
C60 | −0.02597 (17) | 0.54992 (14) | 0.27034 (11) | 0.0305 (4) | |
H60 | 0.0030 | 0.5193 | 0.2380 | 0.0469 (14)* | |
C61 | −0.11659 (17) | 0.53613 (15) | 0.30745 (12) | 0.0338 (4) | |
C62 | −0.15699 (18) | 0.58357 (18) | 0.35354 (14) | 0.0400 (5) | |
H62 | −0.2193 | 0.5761 | 0.3789 | 0.0469 (14)* | |
C63 | −0.10865 (17) | 0.64094 (18) | 0.36317 (13) | 0.0369 (5) | |
H63 | −0.1388 | 0.6728 | 0.3945 | 0.0469 (14)* | |
C64 | −0.1689 (2) | 0.47244 (18) | 0.29886 (16) | 0.0472 (6) | |
H64A | −0.1602 | 0.4183 | 0.3423 | 0.106 (3)* | |
H64B | −0.1392 | 0.4560 | 0.2571 | 0.106 (3)* | |
H64C | −0.2414 | 0.5013 | 0.2916 | 0.106 (3)* | |
C65 | 0.1875 (4) | 0.4008 (3) | 0.1394 (2) | 0.0919 (15) | |
H65A | 0.1846 | 0.4431 | 0.0890 | 0.29 (2)* | |
H65B | 0.2077 | 0.4289 | 0.1695 | 0.29 (2)* | |
C66 | 0.5967 (3) | 0.3714 (3) | 0.2011 (3) | 0.0912 (14) | |
H66A | 0.5736 | 0.4342 | 0.1993 | 0.29 (2)* | |
H66B | 0.6214 | 0.3731 | 0.1520 | 0.29 (2)* | |
C67 | 0.2918 (7) | 0.9320 (7) | 0.4998 (4) | 0.163 (3) | |
H67A | 0.3267 | 0.8674 | 0.5188 | 0.29 (2)* | |
H67B | 0.2742 | 0.9471 | 0.4494 | 0.29 (2)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0293 (2) | 0.0315 (2) | 0.0257 (2) | −0.00463 (18) | −0.00809 (17) | −0.01082 (17) |
Cl2 | 0.0250 (2) | 0.0371 (3) | 0.0434 (3) | 0.00297 (19) | −0.00607 (19) | −0.0242 (2) |
Cl3 | 0.0425 (3) | 0.0246 (2) | 0.0295 (2) | −0.0111 (2) | 0.00268 (19) | −0.01049 (17) |
Cl4 | 0.0274 (2) | 0.0286 (2) | 0.0291 (2) | −0.00885 (18) | −0.00310 (17) | 0.00050 (17) |
Cl5 | 0.0232 (2) | 0.0271 (2) | 0.0230 (2) | −0.00316 (16) | −0.00587 (15) | −0.00730 (16) |
Cl6 | 0.0549 (3) | 0.0432 (3) | 0.0320 (3) | −0.0229 (3) | 0.0122 (2) | −0.0233 (2) |
Cl7 | 0.1084 (10) | 0.0785 (7) | 0.1679 (14) | −0.0319 (7) | −0.0553 (10) | −0.0246 (8) |
Cl8 | 0.1329 (11) | 0.1242 (11) | 0.1277 (11) | −0.0613 (9) | 0.0420 (9) | −0.0908 (9) |
Cl9 | 0.0704 (8) | 0.1312 (12) | 0.275 (2) | −0.0407 (8) | 0.0441 (11) | −0.1200 (15) |
Cl10 | 0.0960 (9) | 0.1779 (15) | 0.1115 (10) | 0.0287 (10) | −0.0305 (8) | −0.0906 (11) |
Cl11 | 0.295 (4) | 0.314 (4) | 0.176 (2) | −0.165 (3) | 0.069 (2) | −0.178 (3) |
Cl12 | 0.143 (2) | 0.310 (5) | 0.872 (14) | −0.072 (3) | 0.040 (4) | −0.366 (7) |
O1 | 0.0309 (7) | 0.0215 (6) | 0.0212 (6) | −0.0038 (5) | −0.0003 (5) | −0.0076 (5) |
O2 | 0.0230 (6) | 0.0194 (6) | 0.0214 (6) | −0.0024 (5) | −0.0018 (5) | −0.0084 (5) |
O3 | 0.0229 (6) | 0.0195 (6) | 0.0199 (6) | −0.0036 (5) | −0.0022 (5) | −0.0073 (5) |
O4 | 0.0200 (6) | 0.0202 (6) | 0.0214 (6) | −0.0034 (5) | −0.0025 (5) | −0.0066 (5) |
O5 | 0.0246 (6) | 0.0240 (6) | 0.0221 (6) | −0.0069 (5) | 0.0004 (5) | −0.0097 (5) |
B1 | 0.0228 (9) | 0.0208 (9) | 0.0218 (9) | −0.0036 (7) | −0.0022 (7) | −0.0074 (7) |
B2 | 0.0246 (10) | 0.0227 (9) | 0.0209 (9) | −0.0045 (7) | −0.0006 (7) | −0.0081 (7) |
B3 | 0.0232 (9) | 0.0194 (8) | 0.0216 (9) | −0.0051 (7) | −0.0011 (7) | −0.0067 (7) |
B4 | 0.0259 (10) | 0.0218 (9) | 0.0200 (8) | −0.0056 (7) | −0.0024 (7) | −0.0081 (7) |
B5 | 0.0260 (10) | 0.0221 (9) | 0.0256 (9) | −0.0038 (8) | −0.0008 (8) | −0.0096 (7) |
B6 | 0.0235 (9) | 0.0219 (9) | 0.0216 (9) | −0.0053 (7) | −0.0021 (7) | −0.0061 (7) |
B7 | 0.0199 (9) | 0.0226 (9) | 0.0218 (9) | −0.0037 (7) | −0.0024 (7) | −0.0089 (7) |
B8 | 0.0298 (11) | 0.0270 (10) | 0.0231 (9) | −0.0076 (8) | 0.0012 (8) | −0.0096 (8) |
C1 | 0.0254 (9) | 0.0217 (8) | 0.0221 (8) | −0.0061 (7) | −0.0023 (6) | −0.0087 (6) |
C2 | 0.0247 (9) | 0.0223 (8) | 0.0233 (8) | −0.0057 (7) | −0.0032 (6) | −0.0093 (6) |
C3 | 0.0265 (9) | 0.0210 (8) | 0.0219 (8) | −0.0036 (7) | −0.0006 (7) | −0.0076 (6) |
C4 | 0.0380 (11) | 0.0291 (9) | 0.0275 (9) | −0.0065 (8) | −0.0066 (8) | −0.0102 (8) |
C5 | 0.0450 (13) | 0.0433 (12) | 0.0250 (10) | −0.0062 (10) | −0.0118 (9) | −0.0080 (9) |
C6 | 0.0375 (12) | 0.0312 (10) | 0.0263 (9) | −0.0014 (9) | 0.0002 (8) | −0.0042 (8) |
C7 | 0.0515 (14) | 0.0224 (9) | 0.0353 (11) | −0.0068 (9) | −0.0043 (10) | −0.0063 (8) |
C8 | 0.0466 (13) | 0.0250 (9) | 0.0301 (10) | −0.0079 (9) | −0.0080 (9) | −0.0083 (8) |
C9 | 0.0543 (16) | 0.0393 (13) | 0.0323 (11) | −0.0017 (11) | −0.0065 (11) | 0.0058 (10) |
C10 | 0.0320 (10) | 0.0235 (8) | 0.0219 (8) | −0.0039 (7) | −0.0018 (7) | −0.0099 (7) |
C11 | 0.0420 (12) | 0.0308 (10) | 0.0360 (11) | −0.0038 (9) | −0.0093 (9) | −0.0171 (9) |
C12 | 0.0655 (17) | 0.0345 (11) | 0.0387 (12) | −0.0034 (11) | −0.0127 (11) | −0.0220 (10) |
C13 | 0.0618 (17) | 0.0351 (12) | 0.0360 (12) | −0.0009 (11) | −0.0004 (11) | −0.0207 (10) |
C14 | 0.0427 (14) | 0.0456 (14) | 0.0448 (13) | 0.0084 (11) | −0.0025 (11) | −0.0241 (11) |
C15 | 0.0354 (11) | 0.0379 (11) | 0.0331 (10) | −0.0023 (9) | −0.0033 (8) | −0.0186 (9) |
C16 | 0.095 (3) | 0.061 (2) | 0.064 (2) | 0.0179 (19) | −0.0072 (19) | −0.0459 (17) |
C17 | 0.0274 (9) | 0.0256 (9) | 0.0219 (8) | −0.0027 (7) | −0.0014 (7) | −0.0102 (7) |
C18 | 0.0223 (9) | 0.0273 (9) | 0.0264 (8) | −0.0031 (7) | 0.0009 (7) | −0.0136 (7) |
C19 | 0.0328 (10) | 0.0270 (9) | 0.0221 (8) | −0.0048 (8) | −0.0005 (7) | −0.0107 (7) |
C20 | 0.0334 (11) | 0.0325 (10) | 0.0292 (10) | −0.0013 (8) | −0.0068 (8) | −0.0130 (8) |
C21 | 0.0447 (13) | 0.0312 (11) | 0.0352 (11) | −0.0020 (9) | −0.0144 (10) | −0.0074 (9) |
C22 | 0.0555 (15) | 0.0384 (12) | 0.0281 (10) | −0.0160 (11) | −0.0073 (10) | −0.0056 (9) |
C23 | 0.0632 (18) | 0.0499 (15) | 0.0270 (11) | −0.0048 (13) | 0.0074 (11) | −0.0098 (10) |
C24 | 0.0520 (15) | 0.0358 (12) | 0.0290 (10) | 0.0041 (10) | 0.0071 (10) | −0.0108 (9) |
C25 | 0.082 (2) | 0.0570 (17) | 0.0329 (13) | −0.0219 (16) | −0.0149 (14) | 0.0030 (12) |
C26 | 0.0289 (10) | 0.0289 (9) | 0.0266 (9) | −0.0060 (8) | 0.0009 (7) | −0.0156 (7) |
C27 | 0.0329 (11) | 0.0322 (10) | 0.0352 (10) | −0.0040 (8) | −0.0029 (8) | −0.0181 (8) |
C28 | 0.0400 (12) | 0.0335 (11) | 0.0424 (12) | −0.0060 (9) | 0.0019 (9) | −0.0236 (9) |
C29 | 0.0417 (13) | 0.0459 (13) | 0.0411 (12) | −0.0159 (10) | 0.0064 (10) | −0.0287 (10) |
C30 | 0.0342 (12) | 0.0523 (14) | 0.0437 (13) | −0.0099 (10) | −0.0043 (10) | −0.0279 (11) |
C31 | 0.0309 (11) | 0.0393 (11) | 0.0382 (11) | −0.0035 (9) | −0.0030 (9) | −0.0197 (9) |
C32 | 0.0524 (16) | 0.0639 (18) | 0.074 (2) | −0.0194 (14) | 0.0046 (14) | −0.0514 (16) |
C33 | 0.0227 (8) | 0.0231 (8) | 0.0227 (8) | −0.0039 (7) | −0.0039 (6) | −0.0072 (6) |
C34 | 0.0205 (8) | 0.0227 (8) | 0.0261 (8) | −0.0040 (7) | −0.0012 (6) | −0.0100 (7) |
C35 | 0.0206 (8) | 0.0263 (9) | 0.0243 (8) | −0.0027 (7) | −0.0037 (7) | −0.0043 (7) |
C36 | 0.0385 (12) | 0.0276 (10) | 0.0398 (11) | −0.0014 (9) | −0.0109 (9) | −0.0099 (9) |
C37 | 0.0457 (14) | 0.0288 (11) | 0.0410 (12) | 0.0047 (10) | −0.0062 (10) | −0.0063 (9) |
C38 | 0.0317 (11) | 0.0407 (12) | 0.0284 (10) | 0.0056 (9) | −0.0008 (8) | −0.0013 (9) |
C39 | 0.0288 (10) | 0.0454 (12) | 0.0255 (9) | −0.0051 (9) | −0.0072 (8) | −0.0038 (9) |
C40 | 0.0262 (10) | 0.0335 (10) | 0.0284 (9) | −0.0050 (8) | −0.0062 (7) | −0.0074 (8) |
C41 | 0.0456 (15) | 0.0537 (17) | 0.0453 (15) | 0.0150 (13) | −0.0137 (12) | 0.0012 (12) |
C42 | 0.0226 (9) | 0.0266 (9) | 0.0276 (9) | −0.0068 (7) | −0.0006 (7) | −0.0105 (7) |
C43 | 0.0291 (11) | 0.0294 (10) | 0.0660 (16) | −0.0079 (9) | 0.0135 (11) | −0.0176 (10) |
C44 | 0.0458 (15) | 0.0355 (13) | 0.115 (3) | −0.0227 (12) | 0.0334 (17) | −0.0321 (16) |
C45 | 0.0322 (13) | 0.0479 (15) | 0.098 (2) | −0.0220 (11) | 0.0235 (14) | −0.0359 (16) |
C46 | 0.0245 (10) | 0.0435 (12) | 0.0456 (12) | −0.0096 (9) | 0.0039 (9) | −0.0225 (10) |
C47 | 0.0235 (9) | 0.0314 (10) | 0.0305 (9) | −0.0063 (8) | −0.0025 (7) | −0.0105 (8) |
C48 | 0.0446 (18) | 0.068 (2) | 0.191 (5) | −0.0352 (17) | 0.050 (2) | −0.063 (3) |
C49 | 0.0240 (9) | 0.0271 (9) | 0.0224 (8) | −0.0061 (7) | −0.0003 (7) | −0.0065 (7) |
C50 | 0.0219 (8) | 0.0239 (8) | 0.0239 (8) | −0.0041 (7) | −0.0022 (6) | −0.0073 (7) |
C51 | 0.0265 (9) | 0.0319 (9) | 0.0216 (8) | −0.0082 (8) | 0.0014 (7) | −0.0093 (7) |
C52 | 0.0333 (11) | 0.0347 (11) | 0.0300 (10) | −0.0114 (9) | −0.0038 (8) | −0.0046 (8) |
C53 | 0.0435 (13) | 0.0448 (13) | 0.0266 (10) | −0.0200 (11) | −0.0005 (9) | −0.0033 (9) |
C54 | 0.0531 (15) | 0.0574 (15) | 0.0256 (10) | −0.0311 (13) | 0.0092 (9) | −0.0161 (10) |
C55 | 0.0440 (13) | 0.0483 (13) | 0.0347 (11) | −0.0142 (11) | 0.0124 (10) | −0.0210 (10) |
C56 | 0.0388 (12) | 0.0328 (10) | 0.0291 (10) | −0.0082 (9) | 0.0052 (8) | −0.0110 (8) |
C57 | 0.099 (3) | 0.081 (2) | 0.0394 (14) | −0.049 (2) | 0.0325 (16) | −0.0260 (15) |
C58 | 0.0213 (8) | 0.0273 (9) | 0.0254 (8) | −0.0059 (7) | −0.0039 (7) | −0.0064 (7) |
C59 | 0.0244 (9) | 0.0286 (9) | 0.0252 (8) | −0.0079 (7) | −0.0019 (7) | −0.0071 (7) |
C60 | 0.0334 (11) | 0.0281 (9) | 0.0291 (9) | −0.0089 (8) | −0.0056 (8) | −0.0066 (7) |
C61 | 0.0297 (10) | 0.0332 (10) | 0.0381 (11) | −0.0123 (8) | −0.0081 (8) | −0.0067 (9) |
C62 | 0.0253 (10) | 0.0529 (14) | 0.0470 (13) | −0.0169 (10) | 0.0014 (9) | −0.0191 (11) |
C63 | 0.0277 (10) | 0.0533 (14) | 0.0390 (11) | −0.0156 (10) | 0.0048 (9) | −0.0245 (10) |
C64 | 0.0463 (14) | 0.0402 (13) | 0.0597 (16) | −0.0199 (11) | −0.0094 (12) | −0.0137 (12) |
C65 | 0.152 (5) | 0.070 (2) | 0.075 (3) | −0.060 (3) | 0.025 (3) | −0.035 (2) |
C66 | 0.059 (2) | 0.080 (3) | 0.109 (4) | −0.007 (2) | −0.002 (2) | −0.013 (3) |
C67 | 0.190 (8) | 0.219 (9) | 0.142 (6) | −0.110 (7) | −0.001 (6) | −0.092 (6) |
Cl1—B4 | 1.814 (2) | C26—C27 | 1.400 (3) |
Cl2—B5 | 1.836 (2) | C26—C31 | 1.407 (3) |
Cl3—B5 | 1.833 (2) | C27—C28 | 1.391 (3) |
Cl4—B6 | 1.734 (2) | C27—H27 | 0.9500 |
Cl5—B7 | 1.840 (2) | C28—C29 | 1.381 (4) |
Cl6—B8 | 1.727 (2) | C28—H28 | 0.9500 |
Cl7—C65 | 1.719 (5) | C29—C30 | 1.394 (4) |
Cl8—C65 | 1.746 (5) | C29—C32 | 1.512 (3) |
Cl9—C66 | 1.685 (5) | C30—C31 | 1.391 (3) |
Cl10—C66 | 1.708 (5) | C30—H30 | 0.9500 |
Cl11—C67 | 1.655 (9) | C31—H31 | 0.9500 |
Cl12—C67 | 1.641 (8) | C32—H32A | 0.9800 |
O1—B1 | 1.353 (2) | C32—H32B | 0.9800 |
O1—B2 | 1.363 (2) | C32—H32C | 0.9800 |
O2—B2 | 1.426 (2) | C33—C34 | 1.366 (3) |
O2—B3 | 1.497 (2) | C33—C35 | 1.482 (3) |
O2—B5 | 1.623 (2) | C34—C42 | 1.479 (3) |
O3—B1 | 1.433 (2) | C35—C40 | 1.390 (3) |
O3—B3 | 1.495 (2) | C35—C36 | 1.394 (3) |
O3—B4 | 1.555 (2) | C36—C37 | 1.393 (3) |
O4—B6 | 1.428 (2) | C36—H36 | 0.9500 |
O4—B7 | 1.531 (2) | C37—C38 | 1.388 (4) |
O4—B3 | 1.565 (2) | C37—H37 | 0.9500 |
O5—B8 | 1.414 (2) | C38—C39 | 1.381 (4) |
O5—B4 | 1.549 (2) | C38—C41 | 1.510 (3) |
O5—B7 | 1.557 (2) | C39—C40 | 1.394 (3) |
B1—C1 | 1.529 (3) | C39—H39 | 0.9500 |
B2—C17 | 1.531 (3) | C40—H40 | 0.9500 |
B3—C34 | 1.589 (3) | C41—H41A | 0.9800 |
B4—C2 | 1.596 (3) | C41—H41B | 0.9800 |
B5—C18 | 1.594 (3) | C41—H41C | 0.9800 |
B6—C33 | 1.521 (3) | C42—C43 | 1.386 (3) |
B7—C50 | 1.598 (3) | C42—C47 | 1.398 (3) |
B8—C49 | 1.533 (3) | C43—C44 | 1.390 (3) |
C1—C2 | 1.363 (3) | C43—H43 | 0.9500 |
C1—C3 | 1.480 (3) | C44—C45 | 1.385 (4) |
C2—C10 | 1.476 (3) | C44—H44 | 0.9500 |
C3—C4 | 1.389 (3) | C45—C46 | 1.377 (4) |
C3—C8 | 1.399 (3) | C45—C48 | 1.510 (4) |
C4—C5 | 1.384 (3) | C46—C47 | 1.387 (3) |
C4—H4 | 0.9500 | C46—H46 | 0.9500 |
C5—C6 | 1.388 (4) | C47—H47 | 0.9500 |
C5—H5 | 0.9500 | C48—H48A | 0.9800 |
C6—C7 | 1.385 (3) | C48—H48B | 0.9800 |
C6—C9 | 1.509 (3) | C48—H48C | 0.9800 |
C7—C8 | 1.389 (3) | C49—C50 | 1.367 (3) |
C7—H7 | 0.9500 | C49—C51 | 1.480 (3) |
C8—H8 | 0.9500 | C50—C58 | 1.476 (3) |
C9—H9A | 0.9800 | C51—C56 | 1.388 (3) |
C9—H9B | 0.9800 | C51—C52 | 1.400 (3) |
C9—H9C | 0.9800 | C52—C53 | 1.391 (3) |
C10—C15 | 1.381 (3) | C52—H52 | 0.9500 |
C10—C11 | 1.398 (3) | C53—C54 | 1.379 (4) |
C11—C12 | 1.385 (3) | C53—H53 | 0.9500 |
C11—H11 | 0.9500 | C54—C55 | 1.386 (4) |
C12—C13 | 1.390 (4) | C54—C57 | 1.516 (3) |
C12—H12 | 0.9500 | C55—C56 | 1.394 (3) |
C13—C14 | 1.383 (4) | C55—H55 | 0.9500 |
C13—C16 | 1.504 (4) | C56—H56 | 0.9500 |
C14—C15 | 1.382 (3) | C57—H57A | 0.9800 |
C14—H14 | 0.9500 | C57—H57B | 0.9800 |
C15—H15 | 0.9500 | C57—H57C | 0.9800 |
C16—H16A | 0.9800 | C58—C59 | 1.394 (3) |
C16—H16B | 0.9800 | C58—C63 | 1.399 (3) |
C16—H16C | 0.9800 | C59—C60 | 1.391 (3) |
C17—C18 | 1.363 (3) | C59—H59 | 0.9500 |
C17—C19 | 1.478 (3) | C60—C61 | 1.394 (3) |
C18—C26 | 1.482 (3) | C60—H60 | 0.9500 |
C19—C20 | 1.391 (3) | C61—C62 | 1.395 (4) |
C19—C24 | 1.393 (3) | C61—C64 | 1.498 (3) |
C20—C21 | 1.381 (3) | C62—C63 | 1.378 (3) |
C20—H20 | 0.9500 | C62—H62 | 0.9500 |
C21—C22 | 1.382 (4) | C63—H63 | 0.9500 |
C21—H21 | 0.9500 | C64—H64A | 0.9800 |
C22—C23 | 1.384 (4) | C64—H64B | 0.9800 |
C22—C25 | 1.509 (3) | C64—H64C | 0.9800 |
C23—C24 | 1.385 (3) | C65—H65A | 0.9900 |
C23—H23 | 0.9500 | C65—H65B | 0.9900 |
C24—H24 | 0.9500 | C66—H66A | 0.9900 |
C25—H25A | 0.9800 | C66—H66B | 0.9900 |
C25—H25B | 0.9800 | C67—H67A | 0.9900 |
C25—H25C | 0.9800 | C67—H67B | 0.9900 |
B1—O1—B2 | 122.79 (15) | C28—C29—C30 | 118.3 (2) |
B2—O2—B3 | 125.60 (14) | C28—C29—C32 | 121.3 (2) |
B2—O2—B5 | 105.97 (14) | C30—C29—C32 | 120.4 (2) |
B3—O2—B5 | 128.36 (14) | C31—C30—C29 | 121.3 (2) |
B1—O3—B3 | 125.73 (14) | C31—C30—H30 | 119.4 |
B1—O3—B4 | 107.81 (14) | C29—C30—H30 | 119.4 |
B3—O3—B4 | 124.41 (13) | C30—C31—C26 | 120.1 (2) |
B6—O4—B7 | 130.48 (14) | C30—C31—H31 | 119.9 |
B6—O4—B3 | 105.33 (14) | C26—C31—H31 | 119.9 |
B7—O4—B3 | 118.91 (13) | C29—C32—H32A | 109.5 |
B8—O5—B4 | 129.30 (15) | C29—C32—H32B | 109.5 |
B8—O5—B7 | 107.48 (14) | H32A—C32—H32B | 109.5 |
B4—O5—B7 | 122.62 (13) | C29—C32—H32C | 109.5 |
O1—B1—O3 | 118.14 (16) | H32A—C32—H32C | 109.5 |
O1—B1—C1 | 131.55 (17) | H32B—C32—H32C | 109.5 |
O3—B1—C1 | 110.30 (16) | C34—C33—C35 | 128.08 (17) |
O1—B2—O2 | 118.64 (16) | C34—C33—B6 | 108.69 (16) |
O1—B2—C17 | 129.23 (17) | C35—C33—B6 | 123.13 (16) |
O2—B2—C17 | 112.08 (16) | C33—C34—C42 | 127.77 (18) |
O3—B3—O2 | 107.38 (14) | C33—C34—B3 | 108.92 (16) |
O3—B3—O4 | 103.79 (14) | C42—C34—B3 | 123.04 (16) |
O2—B3—O4 | 108.97 (14) | C40—C35—C36 | 118.15 (19) |
O3—B3—C34 | 118.73 (16) | C40—C35—C33 | 121.81 (18) |
O2—B3—C34 | 113.40 (15) | C36—C35—C33 | 120.03 (19) |
O4—B3—C34 | 103.75 (14) | C37—C36—C35 | 120.5 (2) |
O5—B4—O3 | 101.54 (13) | C37—C36—H36 | 119.7 |
O5—B4—C2 | 113.06 (16) | C35—C36—H36 | 119.7 |
O3—B4—C2 | 102.02 (14) | C38—C37—C36 | 121.1 (2) |
O5—B4—Cl1 | 109.09 (12) | C38—C37—H37 | 119.5 |
O3—B4—Cl1 | 110.44 (13) | C36—C37—H37 | 119.5 |
C2—B4—Cl1 | 119.02 (14) | C39—C38—C37 | 118.4 (2) |
C18—B5—O2 | 100.90 (14) | C39—C38—C41 | 121.1 (3) |
C18—B5—Cl3 | 116.13 (15) | C37—C38—C41 | 120.6 (3) |
O2—B5—Cl3 | 109.02 (13) | C38—C39—C40 | 121.0 (2) |
C18—B5—Cl2 | 111.83 (14) | C38—C39—H39 | 119.5 |
O2—B5—Cl2 | 107.59 (13) | C40—C39—H39 | 119.5 |
Cl3—B5—Cl2 | 110.60 (11) | C35—C40—C39 | 120.8 (2) |
O4—B6—C33 | 111.46 (15) | C35—C40—H40 | 119.6 |
O4—B6—Cl4 | 121.26 (15) | C39—C40—H40 | 119.6 |
C33—B6—Cl4 | 127.13 (15) | C38—C41—H41A | 109.5 |
O4—B7—O5 | 102.44 (14) | C38—C41—H41B | 109.5 |
O4—B7—C50 | 120.03 (15) | H41A—C41—H41B | 109.5 |
O5—B7—C50 | 103.27 (14) | C38—C41—H41C | 109.5 |
O4—B7—Cl5 | 108.22 (12) | H41A—C41—H41C | 109.5 |
O5—B7—Cl5 | 109.96 (12) | H41B—C41—H41C | 109.5 |
C50—B7—Cl5 | 112.08 (13) | C43—C42—C47 | 117.39 (18) |
O5—B8—C49 | 110.84 (17) | C43—C42—C34 | 120.72 (18) |
O5—B8—Cl6 | 122.02 (15) | C47—C42—C34 | 121.89 (17) |
C49—B8—Cl6 | 127.14 (16) | C42—C43—C44 | 121.2 (2) |
C2—C1—C3 | 127.61 (17) | C42—C43—H43 | 119.4 |
C2—C1—B1 | 107.97 (16) | C44—C43—H43 | 119.4 |
C3—C1—B1 | 124.40 (16) | C45—C44—C43 | 120.9 (2) |
C1—C2—C10 | 125.07 (17) | C45—C44—H44 | 119.6 |
C1—C2—B4 | 111.33 (16) | C43—C44—H44 | 119.6 |
C10—C2—B4 | 123.36 (16) | C46—C45—C44 | 118.3 (2) |
C4—C3—C8 | 117.99 (18) | C46—C45—C48 | 119.8 (3) |
C4—C3—C1 | 119.83 (17) | C44—C45—C48 | 122.0 (3) |
C8—C3—C1 | 122.18 (18) | C45—C46—C47 | 121.1 (2) |
C5—C4—C3 | 120.6 (2) | C45—C46—H46 | 119.4 |
C5—C4—H4 | 119.7 | C47—C46—H46 | 119.4 |
C3—C4—H4 | 119.7 | C46—C47—C42 | 121.0 (2) |
C4—C5—C6 | 121.8 (2) | C46—C47—H47 | 119.5 |
C4—C5—H5 | 119.1 | C42—C47—H47 | 119.5 |
C6—C5—H5 | 119.1 | C45—C48—H48A | 109.5 |
C7—C6—C5 | 117.5 (2) | C45—C48—H48B | 109.5 |
C7—C6—C9 | 121.6 (2) | H48A—C48—H48B | 109.5 |
C5—C6—C9 | 120.8 (2) | C45—C48—H48C | 109.5 |
C6—C7—C8 | 121.4 (2) | H48A—C48—H48C | 109.5 |
C6—C7—H7 | 119.3 | H48B—C48—H48C | 109.5 |
C8—C7—H7 | 119.3 | C50—C49—C51 | 128.51 (18) |
C7—C8—C3 | 120.6 (2) | C50—C49—B8 | 108.67 (16) |
C7—C8—H8 | 119.7 | C51—C49—B8 | 122.81 (18) |
C3—C8—H8 | 119.7 | C49—C50—C58 | 127.05 (17) |
C6—C9—H9A | 109.5 | C49—C50—B7 | 109.68 (16) |
C6—C9—H9B | 109.5 | C58—C50—B7 | 122.78 (16) |
H9A—C9—H9B | 109.5 | C56—C51—C52 | 118.83 (19) |
C6—C9—H9C | 109.5 | C56—C51—C49 | 121.06 (18) |
H9A—C9—H9C | 109.5 | C52—C51—C49 | 120.11 (19) |
H9B—C9—H9C | 109.5 | C53—C52—C51 | 120.1 (2) |
C15—C10—C11 | 117.94 (19) | C53—C52—H52 | 120.0 |
C15—C10—C2 | 120.38 (18) | C51—C52—H52 | 120.0 |
C11—C10—C2 | 121.66 (19) | C54—C53—C52 | 121.2 (2) |
C12—C11—C10 | 120.6 (2) | C54—C53—H53 | 119.4 |
C12—C11—H11 | 119.7 | C52—C53—H53 | 119.4 |
C10—C11—H11 | 119.7 | C53—C54—C55 | 118.6 (2) |
C11—C12—C13 | 121.2 (2) | C53—C54—C57 | 121.1 (3) |
C11—C12—H12 | 119.4 | C55—C54—C57 | 120.3 (3) |
C13—C12—H12 | 119.4 | C54—C55—C56 | 121.1 (2) |
C14—C13—C12 | 117.7 (2) | C54—C55—H55 | 119.5 |
C14—C13—C16 | 121.7 (3) | C56—C55—H55 | 119.5 |
C12—C13—C16 | 120.7 (3) | C51—C56—C55 | 120.2 (2) |
C15—C14—C13 | 121.4 (2) | C51—C56—H56 | 119.9 |
C15—C14—H14 | 119.3 | C55—C56—H56 | 119.9 |
C13—C14—H14 | 119.3 | C54—C57—H57A | 109.5 |
C10—C15—C14 | 121.1 (2) | C54—C57—H57B | 109.5 |
C10—C15—H15 | 119.5 | H57A—C57—H57B | 109.5 |
C14—C15—H15 | 119.5 | C54—C57—H57C | 109.5 |
C13—C16—H16A | 109.5 | H57A—C57—H57C | 109.5 |
C13—C16—H16B | 109.5 | H57B—C57—H57C | 109.5 |
H16A—C16—H16B | 109.5 | C59—C58—C63 | 116.95 (19) |
C13—C16—H16C | 109.5 | C59—C58—C50 | 120.09 (17) |
H16A—C16—H16C | 109.5 | C63—C58—C50 | 122.89 (19) |
H16B—C16—H16C | 109.5 | C60—C59—C58 | 121.75 (19) |
C18—C17—C19 | 128.47 (18) | C60—C59—H59 | 119.1 |
C18—C17—B2 | 107.62 (16) | C58—C59—H59 | 119.1 |
C19—C17—B2 | 123.90 (17) | C59—C60—C61 | 120.7 (2) |
C17—C18—C26 | 126.39 (18) | C59—C60—H60 | 119.6 |
C17—C18—B5 | 112.02 (17) | C61—C60—H60 | 119.6 |
C26—C18—B5 | 121.58 (17) | C60—C61—C62 | 117.5 (2) |
C20—C19—C24 | 117.4 (2) | C60—C61—C64 | 121.6 (2) |
C20—C19—C17 | 121.50 (18) | C62—C61—C64 | 120.9 (2) |
C24—C19—C17 | 121.03 (19) | C63—C62—C61 | 121.5 (2) |
C21—C20—C19 | 121.0 (2) | C63—C62—H62 | 119.2 |
C21—C20—H20 | 119.5 | C61—C62—H62 | 119.2 |
C19—C20—H20 | 119.5 | C62—C63—C58 | 121.4 (2) |
C20—C21—C22 | 121.6 (2) | C62—C63—H63 | 119.3 |
C20—C21—H21 | 119.2 | C58—C63—H63 | 119.3 |
C22—C21—H21 | 119.2 | C61—C64—H64A | 109.5 |
C21—C22—C23 | 117.5 (2) | C61—C64—H64B | 109.5 |
C21—C22—C25 | 120.7 (3) | H64A—C64—H64B | 109.5 |
C23—C22—C25 | 121.8 (3) | C61—C64—H64C | 109.5 |
C22—C23—C24 | 121.4 (2) | H64A—C64—H64C | 109.5 |
C22—C23—H23 | 119.3 | H64B—C64—H64C | 109.5 |
C24—C23—H23 | 119.3 | Cl7—C65—Cl8 | 112.7 (2) |
C23—C24—C19 | 120.9 (2) | Cl7—C65—H65A | 109.1 |
C23—C24—H24 | 119.5 | Cl8—C65—H65A | 109.1 |
C19—C24—H24 | 119.5 | Cl7—C65—H65B | 109.1 |
C22—C25—H25A | 109.5 | Cl8—C65—H65B | 109.1 |
C22—C25—H25B | 109.5 | H65A—C65—H65B | 107.8 |
H25A—C25—H25B | 109.5 | Cl9—C66—Cl10 | 116.7 (3) |
C22—C25—H25C | 109.5 | Cl9—C66—H66A | 108.1 |
H25A—C25—H25C | 109.5 | Cl10—C66—H66A | 108.1 |
H25B—C25—H25C | 109.5 | Cl9—C66—H66B | 108.1 |
C27—C26—C31 | 118.35 (19) | Cl10—C66—H66B | 108.1 |
C27—C26—C18 | 121.72 (19) | H66A—C66—H66B | 107.3 |
C31—C26—C18 | 119.73 (19) | Cl12—C67—Cl11 | 113.5 (5) |
C28—C27—C26 | 120.4 (2) | Cl12—C67—H67A | 108.9 |
C28—C27—H27 | 119.8 | Cl11—C67—H67A | 108.9 |
C26—C27—H27 | 119.8 | Cl12—C67—H67B | 108.9 |
C29—C28—C27 | 121.5 (2) | Cl11—C67—H67B | 108.9 |
C29—C28—H28 | 119.2 | H67A—C67—H67B | 107.7 |
C27—C28—H28 | 119.2 | ||
B2—O1—B1—O3 | 15.8 (3) | O2—B5—C18—C17 | 12.3 (2) |
B2—O1—B1—C1 | −164.8 (2) | Cl3—B5—C18—C17 | 129.91 (16) |
B3—O3—B1—O1 | −9.1 (3) | Cl2—B5—C18—C17 | −101.87 (17) |
B4—O3—B1—O1 | −173.28 (16) | O2—B5—C18—C26 | −166.28 (16) |
B3—O3—B1—C1 | 171.43 (15) | Cl3—B5—C18—C26 | −48.6 (2) |
B4—O3—B1—C1 | 7.2 (2) | Cl2—B5—C18—C26 | 79.6 (2) |
B1—O1—B2—O2 | −11.4 (3) | C18—C17—C19—C20 | 140.0 (2) |
B1—O1—B2—C17 | 166.1 (2) | B2—C17—C19—C20 | −41.1 (3) |
B3—O2—B2—O1 | −0.5 (3) | C18—C17—C19—C24 | −42.3 (3) |
B5—O2—B2—O1 | −177.59 (17) | B2—C17—C19—C24 | 136.6 (2) |
B3—O2—B2—C17 | −178.46 (16) | C24—C19—C20—C21 | 1.5 (3) |
B5—O2—B2—C17 | 4.5 (2) | C17—C19—C20—C21 | 179.3 (2) |
B1—O3—B3—O2 | −1.3 (2) | C19—C20—C21—C22 | −2.0 (4) |
B4—O3—B3—O2 | 160.39 (15) | C20—C21—C22—C23 | 1.4 (4) |
B1—O3—B3—O4 | −116.64 (17) | C20—C21—C22—C25 | −179.2 (3) |
B4—O3—B3—O4 | 45.1 (2) | C21—C22—C23—C24 | −0.3 (4) |
B1—O3—B3—C34 | 128.92 (18) | C25—C22—C23—C24 | −179.7 (3) |
B4—O3—B3—C34 | −69.4 (2) | C22—C23—C24—C19 | −0.1 (5) |
B2—O2—B3—O3 | 6.1 (2) | C20—C19—C24—C23 | −0.5 (4) |
B5—O2—B3—O3 | −177.50 (15) | C17—C19—C24—C23 | −178.3 (3) |
B2—O2—B3—O4 | 117.92 (17) | C17—C18—C26—C27 | 147.1 (2) |
B5—O2—B3—O4 | −65.7 (2) | B5—C18—C26—C27 | −34.6 (3) |
B2—O2—B3—C34 | −127.07 (18) | C17—C18—C26—C31 | −38.2 (3) |
B5—O2—B3—C34 | 49.3 (2) | B5—C18—C26—C31 | 140.1 (2) |
B6—O4—B3—O3 | −137.01 (15) | C31—C26—C27—C28 | 0.6 (3) |
B7—O4—B3—O3 | 19.96 (19) | C18—C26—C27—C28 | 175.3 (2) |
B6—O4—B3—O2 | 108.82 (16) | C26—C27—C28—C29 | −1.4 (4) |
B7—O4—B3—O2 | −94.21 (17) | C27—C28—C29—C30 | 0.8 (4) |
B6—O4—B3—C34 | −12.28 (18) | C27—C28—C29—C32 | −178.8 (2) |
B7—O4—B3—C34 | 144.68 (15) | C28—C29—C30—C31 | 0.6 (4) |
B8—O5—B4—O3 | 170.58 (17) | C32—C29—C30—C31 | −179.7 (3) |
B7—O5—B4—O3 | 0.6 (2) | C29—C30—C31—C26 | −1.5 (4) |
B8—O5—B4—C2 | −80.9 (2) | C27—C26—C31—C30 | 0.9 (3) |
B7—O5—B4—C2 | 109.18 (18) | C18—C26—C31—C30 | −174.0 (2) |
B8—O5—B4—Cl1 | 54.0 (2) | O4—B6—C33—C34 | 1.2 (2) |
B7—O5—B4—Cl1 | −115.96 (15) | Cl4—B6—C33—C34 | −174.39 (16) |
B1—O3—B4—O5 | 109.57 (15) | O4—B6—C33—C35 | 177.81 (17) |
B3—O3—B4—O5 | −54.9 (2) | Cl4—B6—C33—C35 | 2.2 (3) |
B1—O3—B4—C2 | −7.32 (18) | C35—C33—C34—C42 | 0.2 (3) |
B3—O3—B4—C2 | −171.81 (15) | B6—C33—C34—C42 | 176.56 (18) |
B1—O3—B4—Cl1 | −134.81 (13) | C35—C33—C34—B3 | 174.21 (18) |
B3—O3—B4—Cl1 | 60.70 (19) | B6—C33—C34—B3 | −9.4 (2) |
B2—O2—B5—C18 | −9.39 (18) | O3—B3—C34—C33 | 128.09 (17) |
B3—O2—B5—C18 | 173.65 (16) | O2—B3—C34—C33 | −104.45 (18) |
B2—O2—B5—Cl3 | −132.13 (14) | O4—B3—C34—C33 | 13.6 (2) |
B3—O2—B5—Cl3 | 50.9 (2) | O3—B3—C34—C42 | −57.5 (2) |
B2—O2—B5—Cl2 | 107.89 (14) | O2—B3—C34—C42 | 69.9 (2) |
B3—O2—B5—Cl2 | −69.1 (2) | O4—B3—C34—C42 | −171.99 (16) |
B7—O4—B6—C33 | −145.69 (17) | C34—C33—C35—C40 | 59.8 (3) |
B3—O4—B6—C33 | 7.5 (2) | B6—C33—C35—C40 | −116.1 (2) |
B7—O4—B6—Cl4 | 30.2 (3) | C34—C33—C35—C36 | −121.5 (2) |
B3—O4—B6—Cl4 | −176.57 (14) | B6—C33—C35—C36 | 62.6 (3) |
B6—O4—B7—O5 | 89.8 (2) | C40—C35—C36—C37 | −1.8 (3) |
B3—O4—B7—O5 | −60.44 (18) | C33—C35—C36—C37 | 179.5 (2) |
B6—O4—B7—C50 | −23.7 (3) | C35—C36—C37—C38 | 1.7 (4) |
B3—O4—B7—C50 | −173.95 (16) | C36—C37—C38—C39 | −0.2 (4) |
B6—O4—B7—Cl5 | −154.03 (15) | C36—C37—C38—C41 | 179.6 (2) |
B3—O4—B7—Cl5 | 55.71 (17) | C37—C38—C39—C40 | −1.1 (3) |
B8—O5—B7—O4 | −123.61 (16) | C41—C38—C39—C40 | 179.1 (2) |
B4—O5—B7—O4 | 48.24 (19) | C36—C35—C40—C39 | 0.5 (3) |
B8—O5—B7—C50 | 1.74 (19) | C33—C35—C40—C39 | 179.16 (19) |
B4—O5—B7—C50 | 173.58 (15) | C38—C39—C40—C35 | 0.9 (3) |
B8—O5—B7—Cl5 | 121.51 (15) | C33—C34—C42—C43 | −148.6 (2) |
B4—O5—B7—Cl5 | −66.64 (18) | B3—C34—C42—C43 | 38.1 (3) |
B4—O5—B8—C49 | −171.52 (17) | C33—C34—C42—C47 | 31.4 (3) |
B7—O5—B8—C49 | −0.4 (2) | B3—C34—C42—C47 | −141.9 (2) |
B4—O5—B8—Cl6 | 9.4 (3) | C47—C42—C43—C44 | −3.5 (4) |
B7—O5—B8—Cl6 | −179.45 (15) | C34—C42—C43—C44 | 176.5 (3) |
O1—B1—C1—C2 | 176.7 (2) | C42—C43—C44—C45 | 2.2 (6) |
O3—B1—C1—C2 | −3.9 (2) | C43—C44—C45—C46 | 1.6 (6) |
O1—B1—C1—C3 | −2.2 (3) | C43—C44—C45—C48 | −178.4 (4) |
O3—B1—C1—C3 | 177.27 (16) | C44—C45—C46—C47 | −4.1 (5) |
C3—C1—C2—C10 | 3.2 (3) | C48—C45—C46—C47 | 175.9 (4) |
B1—C1—C2—C10 | −175.64 (18) | C45—C46—C47—C42 | 2.8 (4) |
C3—C1—C2—B4 | 177.65 (18) | C43—C42—C47—C46 | 1.0 (3) |
B1—C1—C2—B4 | −1.2 (2) | C34—C42—C47—C46 | −179.0 (2) |
O5—B4—C2—C1 | −103.03 (18) | O5—B8—C49—C50 | −1.4 (2) |
O3—B4—C2—C1 | 5.2 (2) | Cl6—B8—C49—C50 | 177.62 (17) |
Cl1—B4—C2—C1 | 126.97 (16) | O5—B8—C49—C51 | 179.60 (18) |
O5—B4—C2—C10 | 71.6 (2) | Cl6—B8—C49—C51 | −1.4 (3) |
O3—B4—C2—C10 | 179.80 (16) | C51—C49—C50—C58 | 9.4 (3) |
Cl1—B4—C2—C10 | −58.4 (2) | B8—C49—C50—C58 | −169.56 (19) |
C2—C1—C3—C4 | −139.2 (2) | C51—C49—C50—B7 | −178.56 (19) |
B1—C1—C3—C4 | 39.5 (3) | B8—C49—C50—B7 | 2.5 (2) |
C2—C1—C3—C8 | 41.1 (3) | O4—B7—C50—C49 | 110.42 (19) |
B1—C1—C3—C8 | −140.3 (2) | O5—B7—C50—C49 | −2.7 (2) |
C8—C3—C4—C5 | −0.9 (3) | Cl5—B7—C50—C49 | −120.96 (16) |
C1—C3—C4—C5 | 179.3 (2) | O4—B7—C50—C58 | −77.1 (2) |
C3—C4—C5—C6 | 1.5 (4) | O5—B7—C50—C58 | 169.80 (16) |
C4—C5—C6—C7 | −1.1 (4) | Cl5—B7—C50—C58 | 51.5 (2) |
C4—C5—C6—C9 | 177.9 (2) | C50—C49—C51—C56 | −120.7 (2) |
C5—C6—C7—C8 | 0.2 (4) | B8—C49—C51—C56 | 58.2 (3) |
C9—C6—C7—C8 | −178.9 (2) | C50—C49—C51—C52 | 59.5 (3) |
C6—C7—C8—C3 | 0.4 (4) | B8—C49—C51—C52 | −121.7 (2) |
C4—C3—C8—C7 | 0.0 (3) | C56—C51—C52—C53 | 1.1 (3) |
C1—C3—C8—C7 | 179.7 (2) | C49—C51—C52—C53 | −179.0 (2) |
C1—C2—C10—C15 | 55.9 (3) | C51—C52—C53—C54 | −0.9 (4) |
B4—C2—C10—C15 | −118.0 (2) | C52—C53—C54—C55 | 0.4 (4) |
C1—C2—C10—C11 | −125.5 (2) | C52—C53—C54—C57 | −180.0 (3) |
B4—C2—C10—C11 | 60.6 (3) | C53—C54—C55—C56 | −0.3 (4) |
C15—C10—C11—C12 | 1.6 (3) | C57—C54—C55—C56 | −179.9 (3) |
C2—C10—C11—C12 | −177.0 (2) | C52—C51—C56—C55 | −1.0 (3) |
C10—C11—C12—C13 | 0.7 (4) | C49—C51—C56—C55 | 179.2 (2) |
C11—C12—C13—C14 | −1.7 (4) | C54—C55—C56—C51 | 0.5 (4) |
C11—C12—C13—C16 | 178.6 (3) | C49—C50—C58—C59 | −167.0 (2) |
C12—C13—C14—C15 | 0.4 (4) | B7—C50—C58—C59 | 22.0 (3) |
C16—C13—C14—C15 | −179.8 (3) | C49—C50—C58—C63 | 16.3 (3) |
C11—C10—C15—C14 | −2.9 (3) | B7—C50—C58—C63 | −154.8 (2) |
C2—C10—C15—C14 | 175.8 (2) | C63—C58—C59—C60 | −2.9 (3) |
C13—C14—C15—C10 | 1.9 (4) | C50—C58—C59—C60 | −179.85 (18) |
O1—B2—C17—C18 | −174.3 (2) | C58—C59—C60—C61 | 1.1 (3) |
O2—B2—C17—C18 | 3.4 (2) | C59—C60—C61—C62 | 0.9 (3) |
O1—B2—C17—C19 | 6.7 (3) | C59—C60—C61—C64 | −178.7 (2) |
O2—B2—C17—C19 | −175.67 (18) | C60—C61—C62—C63 | −1.0 (4) |
C19—C17—C18—C26 | −12.6 (3) | C64—C61—C62—C63 | 178.6 (2) |
B2—C17—C18—C26 | 168.36 (18) | C61—C62—C63—C58 | −0.8 (4) |
C19—C17—C18—B5 | 168.91 (19) | C59—C58—C63—C62 | 2.7 (3) |
B2—C17—C18—B5 | −10.1 (2) | C50—C58—C63—C62 | 179.6 (2) |
Experimental details
Crystal data | |
Chemical formula | C64H56B8Cl6O5·5(CH2Cl2) |
Mr | 1628.90 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 190 |
a, b, c (Å) | 13.7073 (8), 16.5780 (9), 20.0237 (11) |
α, β, γ (°) | 68.135 (1), 82.695 (1), 73.925 (1) |
V (Å3) | 4056.3 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.59 |
Crystal size (mm) | 0.45 × 0.32 × 0.31 |
Data collection | |
Diffractometer | CCD area detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1999) |
Tmin, Tmax | 0.896, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 68074, 25625, 17850 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.725 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.063, 0.214, 1.17 |
No. of reflections | 25625 |
No. of parameters | 841 |
H-atom treatment | Only H-atom displacement parameters refined |
Δρmax, Δρmin (e Å−3) | 1.06, −1.34 |
Computer programs: SMART (Bruker, 1997/98), SAINT (Bruker, 1999), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXL97.
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In an attempt to synthesize 1,4-dichloro-2,3,5,6-tetra(p-tolyl) −1,4-diboracyclohexa-2,5-diene,[(p-CH3C6H4)2C2BCl]2, as a potential precursor for nido-C4B2-carboranes, via thermolysis of 1,2-bis(dichloroboryl)-1,2-bis(p-tolyl)-ethene (I) in toluene, we obtained the title compound, [(CH3C6H4C)8B8O5Cl6], (II), as yellowish crystals. The formation of (II) can be explained by traces of water originating from toluene that was not rigorously dried.
The `tetramer' (II) consists of two oxadiborole rings, (III), that are connected by an oxygen bridge (B—O—B). In addition, two further oxadiborole rings are attached to the diboryloxane derivative, thus forming donor–acceptor bonding systems in which the Cl atom of B3 (from the B3–B6 ring) migrates to atom B5. Compound (II) consists of a bicyclic (B—O)5-building block with three [(p-tolyl-C)2BCl] bridges and one bis-(p-tolyl)ethene bridge. The title compound crystallizes with 5 CH2Cl2 solvate molecules.
In the molecular structure of (II), depicted in Fig.1, different B—O bond lengths are observed. The B—O distances between the sp2-hybridized atoms B1 and B2 and the atom O1 [1.353 (2) and 1.363 (2) Å, respectively] lie in the range of comparable B—O bond lengths in catecholborylalkanes, C6H4O2BR, (B—O = 1.39 Å; Bayer et al., 2002), and oxadiboroles [B—O = 1.374 (3) Å; Köster et al., 1994]. In comparison, the bond lengths B2—O2, B1—O3, B6—O4 and B8—O5 in (2) are elongated [1.414 (2)–1.433 (2) Å] because of the threefold-coordination of the O atoms. The bonds to the sp3-hybridized B atoms are elongated compared with the corresponding bonds of sp2-hybridized B [B—C = 1.589–1.598 (3) versus 1.521–1.533 (3) Å, B—Cl = 1.814–1.840 (2) versus 1.728, 1.734 (2) Å]. For the B—O bonds between sp3 B and threefold-coordinated O atoms the following tendency is observed. B atoms without neighboring Cl atoms form shorter B—O bonds [B3—O2 = 1.497 (2) Å and B3—O3 = 1.495 (2) Å] than those with one chlorine substituent, B4—O3, B4—O5, B7—O4 and B7—O5 [1.531 (2)–1.557 (2) Å], while the B—O bond at B5 bearing two Cl atoms is even longer [1.623 (2) Å]. This observation is explained by the electron-withdrawing properties of the Cl atoms.