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In the title compound, 1,1,6a,7,9a,10-hexa­chloro-2,3,5,6,8,9,11,12-octa-p-tolyl-1,6a,9a,12a-tetraborata-3a,4a,7,10-tetrabora-4a1,6b,9b,12b-tetraoxonia-4-oxatetra­cyclo­penta­[1,2-a:2,1,5-de:1,2-g:1,2-i]­naphthalene di­chloro­methane pentasolvate, C64H56B8Cl6O5·5CH2Cl2, two condensed oxadiborole rings are attached to two further oxadiborole rings in a type of donor-acceptor bonding, thus forming a ten-membered alternating (B-O)5 naphthalene-like arrangement as the central building block.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103004542/jz1549sup1.cif
Contains datablocks global, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103004542/jz1549IIsup2.hkl
Contains datablock II

CCDC reference: 214171

Comment top

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.

Experimental top

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.

Refinement top

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.

Computing details top

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.

Figures top
[Figure 1] 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.
(II) top
Crystal data top
C64H56B8Cl6O5·5(CH2Cl2)Z = 2
Mr = 1628.90F(000) = 1664
Triclinic, P1Dx = 1.334 Mg m3
a = 13.7073 (8) ÅMo Kα radiation, λ = 0.71073 Å
b = 16.5780 (9) ÅCell parameters from 6409 reflections
c = 20.0237 (11) Åθ = 2.3–31.1°
α = 68.135 (1)°µ = 0.59 mm1
β = 82.695 (1)°T = 190 K
γ = 73.925 (1)°Irregular, yellow
V = 4056.3 (4) Å30.45 × 0.32 × 0.31 mm
Data collection top
CCD area detector
diffractometer
25625 independent reflections
Radiation source: fine-focus sealed tube17850 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.034
ω–scanθmax = 31.0°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1999)
h = 1919
Tmin = 0.896, Tmax = 1.000k = 2124
68074 measured reflectionsl = 029
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)] = 0.063Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.214Only 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 parametersΔρmax = 1.06 e Å3
0 restraintsΔρmin = 1.34 e Å3
Crystal data top
C64H56B8Cl6O5·5(CH2Cl2)γ = 73.925 (1)°
Mr = 1628.90V = 4056.3 (4) Å3
Triclinic, P1Z = 2
a = 13.7073 (8) ÅMo Kα radiation
b = 16.5780 (9) ŵ = 0.59 mm1
c = 20.0237 (11) ÅT = 190 K
α = 68.135 (1)°0.45 × 0.32 × 0.31 mm
β = 82.695 (1)°
Data collection top
CCD area detector
diffractometer
25625 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1999)
17850 reflections with I > 2σ(I)
Tmin = 0.896, Tmax = 1.000Rint = 0.034
68074 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0630 restraints
wR(F2) = 0.214Only H-atom displacement parameters refined
S = 1.17Δρmax = 1.06 e Å3
25625 reflectionsΔρmin = 1.34 e Å3
841 parameters
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.31285 (4)0.85585 (3)0.33018 (3)0.02855 (11)
Cl20.46936 (4)0.61044 (4)0.13147 (3)0.03401 (12)
Cl30.26846 (4)0.56737 (3)0.18956 (3)0.03167 (12)
Cl40.22802 (4)0.54846 (3)0.38654 (3)0.03095 (11)
Cl50.05870 (3)0.81519 (3)0.18713 (2)0.02506 (10)
Cl60.08033 (5)0.89154 (4)0.41656 (3)0.03937 (14)
Cl70.27779 (12)0.30328 (9)0.14477 (10)0.1172 (5)
Cl80.06686 (12)0.38298 (10)0.16773 (9)0.1126 (5)
Cl90.49553 (10)0.32663 (12)0.22218 (14)0.1459 (8)
Cl100.69698 (11)0.31809 (14)0.25728 (8)0.1275 (6)
Cl110.1859 (3)0.9499 (2)0.54780 (15)0.2224 (15)
Cl120.3703 (3)0.9905 (3)0.5006 (4)0.397 (4)
O10.23996 (11)0.89955 (9)0.07741 (7)0.0251 (3)
O20.29697 (10)0.74199 (8)0.14407 (7)0.0214 (2)
O30.25621 (10)0.84872 (8)0.20489 (7)0.0209 (2)
O40.22214 (10)0.70389 (8)0.26872 (7)0.0209 (2)
O50.13440 (10)0.83013 (9)0.30358 (7)0.0231 (3)
B10.22115 (16)0.91892 (14)0.13846 (11)0.0221 (4)
B20.26843 (16)0.81386 (14)0.07772 (11)0.0229 (4)
B30.29955 (16)0.75180 (13)0.21513 (11)0.0216 (4)
B40.21402 (16)0.88479 (14)0.26699 (11)0.0222 (4)
B50.33070 (17)0.65099 (14)0.12497 (12)0.0247 (4)
B60.28288 (16)0.62560 (14)0.31929 (11)0.0227 (4)
B70.11458 (15)0.75932 (14)0.27676 (11)0.0213 (4)
B80.07933 (18)0.82327 (15)0.36934 (12)0.0265 (4)
C10.16759 (15)1.00599 (12)0.15161 (10)0.0226 (3)
C20.16406 (15)0.98814 (12)0.22393 (10)0.0228 (3)
C30.12614 (15)1.09259 (12)0.09421 (10)0.0236 (3)
C40.07739 (17)1.09415 (14)0.03687 (11)0.0313 (4)
H40.07151.03950.03460.0469 (14)*
C50.0372 (2)1.17458 (17)0.01693 (12)0.0390 (5)
H50.00281.17410.05500.0469 (14)*
C60.04594 (18)1.25597 (15)0.01675 (11)0.0350 (5)
C70.0951 (2)1.25429 (14)0.04024 (13)0.0378 (5)
H70.10191.30900.04180.0469 (14)*
C80.13449 (19)1.17433 (14)0.09520 (12)0.0339 (4)
H80.16741.17520.13380.0469 (14)*
C90.0046 (2)1.34253 (18)0.07728 (14)0.0491 (7)
H9A0.05781.35490.11450.106 (3)*
H9B0.01751.39180.05860.106 (3)*
H9C0.05331.33710.09800.106 (3)*
C100.11240 (16)1.05286 (13)0.25945 (10)0.0258 (4)
C110.16342 (19)1.07187 (15)0.30580 (12)0.0350 (5)
H110.23391.04490.31320.0469 (14)*
C120.1121 (2)1.12975 (17)0.34106 (14)0.0444 (6)
H120.14821.14240.37200.0469 (14)*
C130.0088 (2)1.16969 (17)0.33209 (14)0.0443 (6)
C140.0405 (2)1.15155 (19)0.28519 (14)0.0460 (6)
H140.11101.17840.27790.0469 (14)*
C150.01058 (18)1.09526 (16)0.24874 (12)0.0349 (5)
H150.02491.08550.21580.0469 (14)*
C160.0464 (3)1.2307 (3)0.3720 (2)0.0737 (11)
H16A0.03211.20070.42340.106 (3)*
H16B0.11961.24490.36540.106 (3)*
H16C0.02351.28630.35340.106 (3)*
C170.27146 (15)0.78013 (13)0.01578 (10)0.0252 (4)
C180.29573 (15)0.68872 (13)0.04375 (10)0.0249 (4)
C190.25240 (16)0.83969 (13)0.05993 (10)0.0273 (4)
C200.17543 (17)0.91854 (15)0.07790 (12)0.0320 (4)
H200.13350.93440.04080.0469 (14)*
C210.1589 (2)0.97423 (16)0.14880 (13)0.0387 (5)
H210.10441.02670.15960.0469 (14)*
C220.2198 (2)0.95552 (17)0.20441 (12)0.0409 (5)
C230.2971 (2)0.87750 (19)0.18669 (13)0.0506 (7)
H230.33990.86280.22390.0469 (14)*
C240.3134 (2)0.82036 (17)0.11593 (12)0.0431 (6)
H240.36700.76720.10540.0469 (14)*
C250.2012 (3)1.0179 (2)0.28141 (15)0.0608 (8)
H25A0.14821.07200.28240.106 (3)*
H25B0.17930.98750.30830.106 (3)*
H25C0.26411.03480.30350.106 (3)*
C260.28945 (16)0.62788 (14)0.00668 (11)0.0268 (4)
C270.35783 (17)0.54364 (15)0.02021 (12)0.0323 (4)
H270.41290.52620.05120.0469 (14)*
C280.34564 (19)0.48539 (16)0.01143 (13)0.0366 (5)
H280.39370.42910.00250.0469 (14)*
C290.26532 (19)0.50754 (17)0.05550 (13)0.0386 (5)
C300.19646 (19)0.59103 (18)0.06862 (14)0.0400 (5)
H300.14040.60700.09840.0469 (14)*
C310.20822 (18)0.65133 (17)0.03893 (13)0.0352 (5)
H310.16130.70840.04950.0469 (14)*
C320.2514 (2)0.4432 (2)0.08865 (19)0.0549 (7)
H32A0.30610.43670.12430.106 (3)*
H32B0.18570.46670.11220.106 (3)*
H32C0.25330.38460.05090.106 (3)*
C330.39488 (14)0.62503 (12)0.30861 (10)0.0231 (3)
C340.40524 (14)0.70177 (12)0.25368 (10)0.0229 (3)
C350.47490 (14)0.55343 (13)0.35515 (10)0.0255 (4)
C360.49254 (19)0.46527 (15)0.35797 (13)0.0365 (5)
H360.45270.45130.33020.0469 (14)*
C370.5680 (2)0.39751 (16)0.40113 (14)0.0428 (6)
H370.58030.33810.40140.0469 (14)*
C380.62566 (18)0.41537 (17)0.44367 (12)0.0400 (5)
C390.60668 (17)0.50232 (17)0.44207 (12)0.0361 (5)
H390.64460.51560.47150.0469 (14)*
C400.53265 (16)0.57096 (15)0.39797 (11)0.0304 (4)
H400.52150.63050.39720.0469 (14)*
C410.7068 (2)0.3412 (2)0.49058 (16)0.0585 (8)
H41A0.76830.36240.48600.106 (3)*
H41B0.72240.28920.47540.106 (3)*
H41C0.68250.32400.54090.106 (3)*
C420.49931 (15)0.73220 (13)0.22695 (10)0.0252 (4)
C430.49644 (18)0.82287 (16)0.19829 (16)0.0426 (6)
H430.43280.86580.19340.0469 (14)*
C440.5850 (2)0.85217 (19)0.1766 (2)0.0646 (10)
H440.58110.91470.15870.0469 (14)*
C450.6787 (2)0.7915 (2)0.1806 (2)0.0561 (8)
C460.68159 (17)0.70144 (17)0.20507 (13)0.0361 (5)
H460.74460.65910.20530.0469 (14)*
C470.59404 (15)0.67156 (14)0.22941 (11)0.0286 (4)
H470.59850.60900.24800.0469 (14)*
C480.7762 (3)0.8213 (3)0.1591 (3)0.0964 (17)
H48A0.77320.86200.10880.106 (3)*
H48B0.83350.76880.16460.106 (3)*
H48C0.78520.85260.19010.106 (3)*
C490.02081 (15)0.75057 (13)0.38952 (10)0.0253 (4)
C500.03738 (14)0.71459 (12)0.33654 (10)0.0238 (3)
C510.04306 (15)0.72811 (14)0.45598 (10)0.0267 (4)
C520.02273 (18)0.64059 (15)0.50646 (12)0.0338 (4)
H520.03280.59570.49840.0469 (14)*
C530.0837 (2)0.61926 (18)0.56840 (12)0.0392 (5)
H530.06990.55950.60200.0469 (14)*
C540.1640 (2)0.68332 (19)0.58192 (12)0.0423 (6)
C550.1835 (2)0.77005 (18)0.53211 (13)0.0412 (5)
H550.23870.81470.54070.0469 (14)*
C560.12348 (18)0.79277 (15)0.46963 (12)0.0343 (4)
H560.13770.85270.43630.0469 (14)*
C570.2302 (3)0.6599 (3)0.64950 (16)0.0694 (10)
H57A0.30030.67060.63620.106 (3)*
H57B0.22820.69730.67710.106 (3)*
H57C0.20500.59650.67890.106 (3)*
C580.01619 (15)0.65329 (13)0.32784 (10)0.0252 (4)
C590.02246 (15)0.60802 (13)0.28011 (10)0.0264 (4)
H590.08350.61710.25350.0469 (14)*
C600.02597 (17)0.54992 (14)0.27034 (11)0.0305 (4)
H600.00300.51930.23800.0469 (14)*
C610.11659 (17)0.53613 (15)0.30745 (12)0.0338 (4)
C620.15699 (18)0.58357 (18)0.35354 (14)0.0400 (5)
H620.21930.57610.37890.0469 (14)*
C630.10865 (17)0.64094 (18)0.36317 (13)0.0369 (5)
H630.13880.67280.39450.0469 (14)*
C640.1689 (2)0.47244 (18)0.29886 (16)0.0472 (6)
H64A0.16020.41830.34230.106 (3)*
H64B0.13920.45600.25710.106 (3)*
H64C0.24140.50130.29160.106 (3)*
C650.1875 (4)0.4008 (3)0.1394 (2)0.0919 (15)
H65A0.18460.44310.08900.29 (2)*
H65B0.20770.42890.16950.29 (2)*
C660.5967 (3)0.3714 (3)0.2011 (3)0.0912 (14)
H66A0.57360.43420.19930.29 (2)*
H66B0.62140.37310.15200.29 (2)*
C670.2918 (7)0.9320 (7)0.4998 (4)0.163 (3)
H67A0.32670.86740.51880.29 (2)*
H67B0.27420.94710.44940.29 (2)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0293 (2)0.0315 (2)0.0257 (2)0.00463 (18)0.00809 (17)0.01082 (17)
Cl20.0250 (2)0.0371 (3)0.0434 (3)0.00297 (19)0.00607 (19)0.0242 (2)
Cl30.0425 (3)0.0246 (2)0.0295 (2)0.0111 (2)0.00268 (19)0.01049 (17)
Cl40.0274 (2)0.0286 (2)0.0291 (2)0.00885 (18)0.00310 (17)0.00050 (17)
Cl50.0232 (2)0.0271 (2)0.0230 (2)0.00316 (16)0.00587 (15)0.00730 (16)
Cl60.0549 (3)0.0432 (3)0.0320 (3)0.0229 (3)0.0122 (2)0.0233 (2)
Cl70.1084 (10)0.0785 (7)0.1679 (14)0.0319 (7)0.0553 (10)0.0246 (8)
Cl80.1329 (11)0.1242 (11)0.1277 (11)0.0613 (9)0.0420 (9)0.0908 (9)
Cl90.0704 (8)0.1312 (12)0.275 (2)0.0407 (8)0.0441 (11)0.1200 (15)
Cl100.0960 (9)0.1779 (15)0.1115 (10)0.0287 (10)0.0305 (8)0.0906 (11)
Cl110.295 (4)0.314 (4)0.176 (2)0.165 (3)0.069 (2)0.178 (3)
Cl120.143 (2)0.310 (5)0.872 (14)0.072 (3)0.040 (4)0.366 (7)
O10.0309 (7)0.0215 (6)0.0212 (6)0.0038 (5)0.0003 (5)0.0076 (5)
O20.0230 (6)0.0194 (6)0.0214 (6)0.0024 (5)0.0018 (5)0.0084 (5)
O30.0229 (6)0.0195 (6)0.0199 (6)0.0036 (5)0.0022 (5)0.0073 (5)
O40.0200 (6)0.0202 (6)0.0214 (6)0.0034 (5)0.0025 (5)0.0066 (5)
O50.0246 (6)0.0240 (6)0.0221 (6)0.0069 (5)0.0004 (5)0.0097 (5)
B10.0228 (9)0.0208 (9)0.0218 (9)0.0036 (7)0.0022 (7)0.0074 (7)
B20.0246 (10)0.0227 (9)0.0209 (9)0.0045 (7)0.0006 (7)0.0081 (7)
B30.0232 (9)0.0194 (8)0.0216 (9)0.0051 (7)0.0011 (7)0.0067 (7)
B40.0259 (10)0.0218 (9)0.0200 (8)0.0056 (7)0.0024 (7)0.0081 (7)
B50.0260 (10)0.0221 (9)0.0256 (9)0.0038 (8)0.0008 (8)0.0096 (7)
B60.0235 (9)0.0219 (9)0.0216 (9)0.0053 (7)0.0021 (7)0.0061 (7)
B70.0199 (9)0.0226 (9)0.0218 (9)0.0037 (7)0.0024 (7)0.0089 (7)
B80.0298 (11)0.0270 (10)0.0231 (9)0.0076 (8)0.0012 (8)0.0096 (8)
C10.0254 (9)0.0217 (8)0.0221 (8)0.0061 (7)0.0023 (6)0.0087 (6)
C20.0247 (9)0.0223 (8)0.0233 (8)0.0057 (7)0.0032 (6)0.0093 (6)
C30.0265 (9)0.0210 (8)0.0219 (8)0.0036 (7)0.0006 (7)0.0076 (6)
C40.0380 (11)0.0291 (9)0.0275 (9)0.0065 (8)0.0066 (8)0.0102 (8)
C50.0450 (13)0.0433 (12)0.0250 (10)0.0062 (10)0.0118 (9)0.0080 (9)
C60.0375 (12)0.0312 (10)0.0263 (9)0.0014 (9)0.0002 (8)0.0042 (8)
C70.0515 (14)0.0224 (9)0.0353 (11)0.0068 (9)0.0043 (10)0.0063 (8)
C80.0466 (13)0.0250 (9)0.0301 (10)0.0079 (9)0.0080 (9)0.0083 (8)
C90.0543 (16)0.0393 (13)0.0323 (11)0.0017 (11)0.0065 (11)0.0058 (10)
C100.0320 (10)0.0235 (8)0.0219 (8)0.0039 (7)0.0018 (7)0.0099 (7)
C110.0420 (12)0.0308 (10)0.0360 (11)0.0038 (9)0.0093 (9)0.0171 (9)
C120.0655 (17)0.0345 (11)0.0387 (12)0.0034 (11)0.0127 (11)0.0220 (10)
C130.0618 (17)0.0351 (12)0.0360 (12)0.0009 (11)0.0004 (11)0.0207 (10)
C140.0427 (14)0.0456 (14)0.0448 (13)0.0084 (11)0.0025 (11)0.0241 (11)
C150.0354 (11)0.0379 (11)0.0331 (10)0.0023 (9)0.0033 (8)0.0186 (9)
C160.095 (3)0.061 (2)0.064 (2)0.0179 (19)0.0072 (19)0.0459 (17)
C170.0274 (9)0.0256 (9)0.0219 (8)0.0027 (7)0.0014 (7)0.0102 (7)
C180.0223 (9)0.0273 (9)0.0264 (8)0.0031 (7)0.0009 (7)0.0136 (7)
C190.0328 (10)0.0270 (9)0.0221 (8)0.0048 (8)0.0005 (7)0.0107 (7)
C200.0334 (11)0.0325 (10)0.0292 (10)0.0013 (8)0.0068 (8)0.0130 (8)
C210.0447 (13)0.0312 (11)0.0352 (11)0.0020 (9)0.0144 (10)0.0074 (9)
C220.0555 (15)0.0384 (12)0.0281 (10)0.0160 (11)0.0073 (10)0.0056 (9)
C230.0632 (18)0.0499 (15)0.0270 (11)0.0048 (13)0.0074 (11)0.0098 (10)
C240.0520 (15)0.0358 (12)0.0290 (10)0.0041 (10)0.0071 (10)0.0108 (9)
C250.082 (2)0.0570 (17)0.0329 (13)0.0219 (16)0.0149 (14)0.0030 (12)
C260.0289 (10)0.0289 (9)0.0266 (9)0.0060 (8)0.0009 (7)0.0156 (7)
C270.0329 (11)0.0322 (10)0.0352 (10)0.0040 (8)0.0029 (8)0.0181 (8)
C280.0400 (12)0.0335 (11)0.0424 (12)0.0060 (9)0.0019 (9)0.0236 (9)
C290.0417 (13)0.0459 (13)0.0411 (12)0.0159 (10)0.0064 (10)0.0287 (10)
C300.0342 (12)0.0523 (14)0.0437 (13)0.0099 (10)0.0043 (10)0.0279 (11)
C310.0309 (11)0.0393 (11)0.0382 (11)0.0035 (9)0.0030 (9)0.0197 (9)
C320.0524 (16)0.0639 (18)0.074 (2)0.0194 (14)0.0046 (14)0.0514 (16)
C330.0227 (8)0.0231 (8)0.0227 (8)0.0039 (7)0.0039 (6)0.0072 (6)
C340.0205 (8)0.0227 (8)0.0261 (8)0.0040 (7)0.0012 (6)0.0100 (7)
C350.0206 (8)0.0263 (9)0.0243 (8)0.0027 (7)0.0037 (7)0.0043 (7)
C360.0385 (12)0.0276 (10)0.0398 (11)0.0014 (9)0.0109 (9)0.0099 (9)
C370.0457 (14)0.0288 (11)0.0410 (12)0.0047 (10)0.0062 (10)0.0063 (9)
C380.0317 (11)0.0407 (12)0.0284 (10)0.0056 (9)0.0008 (8)0.0013 (9)
C390.0288 (10)0.0454 (12)0.0255 (9)0.0051 (9)0.0072 (8)0.0038 (9)
C400.0262 (10)0.0335 (10)0.0284 (9)0.0050 (8)0.0062 (7)0.0074 (8)
C410.0456 (15)0.0537 (17)0.0453 (15)0.0150 (13)0.0137 (12)0.0012 (12)
C420.0226 (9)0.0266 (9)0.0276 (9)0.0068 (7)0.0006 (7)0.0105 (7)
C430.0291 (11)0.0294 (10)0.0660 (16)0.0079 (9)0.0135 (11)0.0176 (10)
C440.0458 (15)0.0355 (13)0.115 (3)0.0227 (12)0.0334 (17)0.0321 (16)
C450.0322 (13)0.0479 (15)0.098 (2)0.0220 (11)0.0235 (14)0.0359 (16)
C460.0245 (10)0.0435 (12)0.0456 (12)0.0096 (9)0.0039 (9)0.0225 (10)
C470.0235 (9)0.0314 (10)0.0305 (9)0.0063 (8)0.0025 (7)0.0105 (8)
C480.0446 (18)0.068 (2)0.191 (5)0.0352 (17)0.050 (2)0.063 (3)
C490.0240 (9)0.0271 (9)0.0224 (8)0.0061 (7)0.0003 (7)0.0065 (7)
C500.0219 (8)0.0239 (8)0.0239 (8)0.0041 (7)0.0022 (6)0.0073 (7)
C510.0265 (9)0.0319 (9)0.0216 (8)0.0082 (8)0.0014 (7)0.0093 (7)
C520.0333 (11)0.0347 (11)0.0300 (10)0.0114 (9)0.0038 (8)0.0046 (8)
C530.0435 (13)0.0448 (13)0.0266 (10)0.0200 (11)0.0005 (9)0.0033 (9)
C540.0531 (15)0.0574 (15)0.0256 (10)0.0311 (13)0.0092 (9)0.0161 (10)
C550.0440 (13)0.0483 (13)0.0347 (11)0.0142 (11)0.0124 (10)0.0210 (10)
C560.0388 (12)0.0328 (10)0.0291 (10)0.0082 (9)0.0052 (8)0.0110 (8)
C570.099 (3)0.081 (2)0.0394 (14)0.049 (2)0.0325 (16)0.0260 (15)
C580.0213 (8)0.0273 (9)0.0254 (8)0.0059 (7)0.0039 (7)0.0064 (7)
C590.0244 (9)0.0286 (9)0.0252 (8)0.0079 (7)0.0019 (7)0.0071 (7)
C600.0334 (11)0.0281 (9)0.0291 (9)0.0089 (8)0.0056 (8)0.0066 (7)
C610.0297 (10)0.0332 (10)0.0381 (11)0.0123 (8)0.0081 (8)0.0067 (9)
C620.0253 (10)0.0529 (14)0.0470 (13)0.0169 (10)0.0014 (9)0.0191 (11)
C630.0277 (10)0.0533 (14)0.0390 (11)0.0156 (10)0.0048 (9)0.0245 (10)
C640.0463 (14)0.0402 (13)0.0597 (16)0.0199 (11)0.0094 (12)0.0137 (12)
C650.152 (5)0.070 (2)0.075 (3)0.060 (3)0.025 (3)0.035 (2)
C660.059 (2)0.080 (3)0.109 (4)0.007 (2)0.002 (2)0.013 (3)
C670.190 (8)0.219 (9)0.142 (6)0.110 (7)0.001 (6)0.092 (6)
Geometric parameters (Å, º) top
Cl1—B41.814 (2)C26—C271.400 (3)
Cl2—B51.836 (2)C26—C311.407 (3)
Cl3—B51.833 (2)C27—C281.391 (3)
Cl4—B61.734 (2)C27—H270.9500
Cl5—B71.840 (2)C28—C291.381 (4)
Cl6—B81.727 (2)C28—H280.9500
Cl7—C651.719 (5)C29—C301.394 (4)
Cl8—C651.746 (5)C29—C321.512 (3)
Cl9—C661.685 (5)C30—C311.391 (3)
Cl10—C661.708 (5)C30—H300.9500
Cl11—C671.655 (9)C31—H310.9500
Cl12—C671.641 (8)C32—H32A0.9800
O1—B11.353 (2)C32—H32B0.9800
O1—B21.363 (2)C32—H32C0.9800
O2—B21.426 (2)C33—C341.366 (3)
O2—B31.497 (2)C33—C351.482 (3)
O2—B51.623 (2)C34—C421.479 (3)
O3—B11.433 (2)C35—C401.390 (3)
O3—B31.495 (2)C35—C361.394 (3)
O3—B41.555 (2)C36—C371.393 (3)
O4—B61.428 (2)C36—H360.9500
O4—B71.531 (2)C37—C381.388 (4)
O4—B31.565 (2)C37—H370.9500
O5—B81.414 (2)C38—C391.381 (4)
O5—B41.549 (2)C38—C411.510 (3)
O5—B71.557 (2)C39—C401.394 (3)
B1—C11.529 (3)C39—H390.9500
B2—C171.531 (3)C40—H400.9500
B3—C341.589 (3)C41—H41A0.9800
B4—C21.596 (3)C41—H41B0.9800
B5—C181.594 (3)C41—H41C0.9800
B6—C331.521 (3)C42—C431.386 (3)
B7—C501.598 (3)C42—C471.398 (3)
B8—C491.533 (3)C43—C441.390 (3)
C1—C21.363 (3)C43—H430.9500
C1—C31.480 (3)C44—C451.385 (4)
C2—C101.476 (3)C44—H440.9500
C3—C41.389 (3)C45—C461.377 (4)
C3—C81.399 (3)C45—C481.510 (4)
C4—C51.384 (3)C46—C471.387 (3)
C4—H40.9500C46—H460.9500
C5—C61.388 (4)C47—H470.9500
C5—H50.9500C48—H48A0.9800
C6—C71.385 (3)C48—H48B0.9800
C6—C91.509 (3)C48—H48C0.9800
C7—C81.389 (3)C49—C501.367 (3)
C7—H70.9500C49—C511.480 (3)
C8—H80.9500C50—C581.476 (3)
C9—H9A0.9800C51—C561.388 (3)
C9—H9B0.9800C51—C521.400 (3)
C9—H9C0.9800C52—C531.391 (3)
C10—C151.381 (3)C52—H520.9500
C10—C111.398 (3)C53—C541.379 (4)
C11—C121.385 (3)C53—H530.9500
C11—H110.9500C54—C551.386 (4)
C12—C131.390 (4)C54—C571.516 (3)
C12—H120.9500C55—C561.394 (3)
C13—C141.383 (4)C55—H550.9500
C13—C161.504 (4)C56—H560.9500
C14—C151.382 (3)C57—H57A0.9800
C14—H140.9500C57—H57B0.9800
C15—H150.9500C57—H57C0.9800
C16—H16A0.9800C58—C591.394 (3)
C16—H16B0.9800C58—C631.399 (3)
C16—H16C0.9800C59—C601.391 (3)
C17—C181.363 (3)C59—H590.9500
C17—C191.478 (3)C60—C611.394 (3)
C18—C261.482 (3)C60—H600.9500
C19—C201.391 (3)C61—C621.395 (4)
C19—C241.393 (3)C61—C641.498 (3)
C20—C211.381 (3)C62—C631.378 (3)
C20—H200.9500C62—H620.9500
C21—C221.382 (4)C63—H630.9500
C21—H210.9500C64—H64A0.9800
C22—C231.384 (4)C64—H64B0.9800
C22—C251.509 (3)C64—H64C0.9800
C23—C241.385 (3)C65—H65A0.9900
C23—H230.9500C65—H65B0.9900
C24—H240.9500C66—H66A0.9900
C25—H25A0.9800C66—H66B0.9900
C25—H25B0.9800C67—H67A0.9900
C25—H25C0.9800C67—H67B0.9900
B1—O1—B2122.79 (15)C28—C29—C30118.3 (2)
B2—O2—B3125.60 (14)C28—C29—C32121.3 (2)
B2—O2—B5105.97 (14)C30—C29—C32120.4 (2)
B3—O2—B5128.36 (14)C31—C30—C29121.3 (2)
B1—O3—B3125.73 (14)C31—C30—H30119.4
B1—O3—B4107.81 (14)C29—C30—H30119.4
B3—O3—B4124.41 (13)C30—C31—C26120.1 (2)
B6—O4—B7130.48 (14)C30—C31—H31119.9
B6—O4—B3105.33 (14)C26—C31—H31119.9
B7—O4—B3118.91 (13)C29—C32—H32A109.5
B8—O5—B4129.30 (15)C29—C32—H32B109.5
B8—O5—B7107.48 (14)H32A—C32—H32B109.5
B4—O5—B7122.62 (13)C29—C32—H32C109.5
O1—B1—O3118.14 (16)H32A—C32—H32C109.5
O1—B1—C1131.55 (17)H32B—C32—H32C109.5
O3—B1—C1110.30 (16)C34—C33—C35128.08 (17)
O1—B2—O2118.64 (16)C34—C33—B6108.69 (16)
O1—B2—C17129.23 (17)C35—C33—B6123.13 (16)
O2—B2—C17112.08 (16)C33—C34—C42127.77 (18)
O3—B3—O2107.38 (14)C33—C34—B3108.92 (16)
O3—B3—O4103.79 (14)C42—C34—B3123.04 (16)
O2—B3—O4108.97 (14)C40—C35—C36118.15 (19)
O3—B3—C34118.73 (16)C40—C35—C33121.81 (18)
O2—B3—C34113.40 (15)C36—C35—C33120.03 (19)
O4—B3—C34103.75 (14)C37—C36—C35120.5 (2)
O5—B4—O3101.54 (13)C37—C36—H36119.7
O5—B4—C2113.06 (16)C35—C36—H36119.7
O3—B4—C2102.02 (14)C38—C37—C36121.1 (2)
O5—B4—Cl1109.09 (12)C38—C37—H37119.5
O3—B4—Cl1110.44 (13)C36—C37—H37119.5
C2—B4—Cl1119.02 (14)C39—C38—C37118.4 (2)
C18—B5—O2100.90 (14)C39—C38—C41121.1 (3)
C18—B5—Cl3116.13 (15)C37—C38—C41120.6 (3)
O2—B5—Cl3109.02 (13)C38—C39—C40121.0 (2)
C18—B5—Cl2111.83 (14)C38—C39—H39119.5
O2—B5—Cl2107.59 (13)C40—C39—H39119.5
Cl3—B5—Cl2110.60 (11)C35—C40—C39120.8 (2)
O4—B6—C33111.46 (15)C35—C40—H40119.6
O4—B6—Cl4121.26 (15)C39—C40—H40119.6
C33—B6—Cl4127.13 (15)C38—C41—H41A109.5
O4—B7—O5102.44 (14)C38—C41—H41B109.5
O4—B7—C50120.03 (15)H41A—C41—H41B109.5
O5—B7—C50103.27 (14)C38—C41—H41C109.5
O4—B7—Cl5108.22 (12)H41A—C41—H41C109.5
O5—B7—Cl5109.96 (12)H41B—C41—H41C109.5
C50—B7—Cl5112.08 (13)C43—C42—C47117.39 (18)
O5—B8—C49110.84 (17)C43—C42—C34120.72 (18)
O5—B8—Cl6122.02 (15)C47—C42—C34121.89 (17)
C49—B8—Cl6127.14 (16)C42—C43—C44121.2 (2)
C2—C1—C3127.61 (17)C42—C43—H43119.4
C2—C1—B1107.97 (16)C44—C43—H43119.4
C3—C1—B1124.40 (16)C45—C44—C43120.9 (2)
C1—C2—C10125.07 (17)C45—C44—H44119.6
C1—C2—B4111.33 (16)C43—C44—H44119.6
C10—C2—B4123.36 (16)C46—C45—C44118.3 (2)
C4—C3—C8117.99 (18)C46—C45—C48119.8 (3)
C4—C3—C1119.83 (17)C44—C45—C48122.0 (3)
C8—C3—C1122.18 (18)C45—C46—C47121.1 (2)
C5—C4—C3120.6 (2)C45—C46—H46119.4
C5—C4—H4119.7C47—C46—H46119.4
C3—C4—H4119.7C46—C47—C42121.0 (2)
C4—C5—C6121.8 (2)C46—C47—H47119.5
C4—C5—H5119.1C42—C47—H47119.5
C6—C5—H5119.1C45—C48—H48A109.5
C7—C6—C5117.5 (2)C45—C48—H48B109.5
C7—C6—C9121.6 (2)H48A—C48—H48B109.5
C5—C6—C9120.8 (2)C45—C48—H48C109.5
C6—C7—C8121.4 (2)H48A—C48—H48C109.5
C6—C7—H7119.3H48B—C48—H48C109.5
C8—C7—H7119.3C50—C49—C51128.51 (18)
C7—C8—C3120.6 (2)C50—C49—B8108.67 (16)
C7—C8—H8119.7C51—C49—B8122.81 (18)
C3—C8—H8119.7C49—C50—C58127.05 (17)
C6—C9—H9A109.5C49—C50—B7109.68 (16)
C6—C9—H9B109.5C58—C50—B7122.78 (16)
H9A—C9—H9B109.5C56—C51—C52118.83 (19)
C6—C9—H9C109.5C56—C51—C49121.06 (18)
H9A—C9—H9C109.5C52—C51—C49120.11 (19)
H9B—C9—H9C109.5C53—C52—C51120.1 (2)
C15—C10—C11117.94 (19)C53—C52—H52120.0
C15—C10—C2120.38 (18)C51—C52—H52120.0
C11—C10—C2121.66 (19)C54—C53—C52121.2 (2)
C12—C11—C10120.6 (2)C54—C53—H53119.4
C12—C11—H11119.7C52—C53—H53119.4
C10—C11—H11119.7C53—C54—C55118.6 (2)
C11—C12—C13121.2 (2)C53—C54—C57121.1 (3)
C11—C12—H12119.4C55—C54—C57120.3 (3)
C13—C12—H12119.4C54—C55—C56121.1 (2)
C14—C13—C12117.7 (2)C54—C55—H55119.5
C14—C13—C16121.7 (3)C56—C55—H55119.5
C12—C13—C16120.7 (3)C51—C56—C55120.2 (2)
C15—C14—C13121.4 (2)C51—C56—H56119.9
C15—C14—H14119.3C55—C56—H56119.9
C13—C14—H14119.3C54—C57—H57A109.5
C10—C15—C14121.1 (2)C54—C57—H57B109.5
C10—C15—H15119.5H57A—C57—H57B109.5
C14—C15—H15119.5C54—C57—H57C109.5
C13—C16—H16A109.5H57A—C57—H57C109.5
C13—C16—H16B109.5H57B—C57—H57C109.5
H16A—C16—H16B109.5C59—C58—C63116.95 (19)
C13—C16—H16C109.5C59—C58—C50120.09 (17)
H16A—C16—H16C109.5C63—C58—C50122.89 (19)
H16B—C16—H16C109.5C60—C59—C58121.75 (19)
C18—C17—C19128.47 (18)C60—C59—H59119.1
C18—C17—B2107.62 (16)C58—C59—H59119.1
C19—C17—B2123.90 (17)C59—C60—C61120.7 (2)
C17—C18—C26126.39 (18)C59—C60—H60119.6
C17—C18—B5112.02 (17)C61—C60—H60119.6
C26—C18—B5121.58 (17)C60—C61—C62117.5 (2)
C20—C19—C24117.4 (2)C60—C61—C64121.6 (2)
C20—C19—C17121.50 (18)C62—C61—C64120.9 (2)
C24—C19—C17121.03 (19)C63—C62—C61121.5 (2)
C21—C20—C19121.0 (2)C63—C62—H62119.2
C21—C20—H20119.5C61—C62—H62119.2
C19—C20—H20119.5C62—C63—C58121.4 (2)
C20—C21—C22121.6 (2)C62—C63—H63119.3
C20—C21—H21119.2C58—C63—H63119.3
C22—C21—H21119.2C61—C64—H64A109.5
C21—C22—C23117.5 (2)C61—C64—H64B109.5
C21—C22—C25120.7 (3)H64A—C64—H64B109.5
C23—C22—C25121.8 (3)C61—C64—H64C109.5
C22—C23—C24121.4 (2)H64A—C64—H64C109.5
C22—C23—H23119.3H64B—C64—H64C109.5
C24—C23—H23119.3Cl7—C65—Cl8112.7 (2)
C23—C24—C19120.9 (2)Cl7—C65—H65A109.1
C23—C24—H24119.5Cl8—C65—H65A109.1
C19—C24—H24119.5Cl7—C65—H65B109.1
C22—C25—H25A109.5Cl8—C65—H65B109.1
C22—C25—H25B109.5H65A—C65—H65B107.8
H25A—C25—H25B109.5Cl9—C66—Cl10116.7 (3)
C22—C25—H25C109.5Cl9—C66—H66A108.1
H25A—C25—H25C109.5Cl10—C66—H66A108.1
H25B—C25—H25C109.5Cl9—C66—H66B108.1
C27—C26—C31118.35 (19)Cl10—C66—H66B108.1
C27—C26—C18121.72 (19)H66A—C66—H66B107.3
C31—C26—C18119.73 (19)Cl12—C67—Cl11113.5 (5)
C28—C27—C26120.4 (2)Cl12—C67—H67A108.9
C28—C27—H27119.8Cl11—C67—H67A108.9
C26—C27—H27119.8Cl12—C67—H67B108.9
C29—C28—C27121.5 (2)Cl11—C67—H67B108.9
C29—C28—H28119.2H67A—C67—H67B107.7
C27—C28—H28119.2
B2—O1—B1—O315.8 (3)O2—B5—C18—C1712.3 (2)
B2—O1—B1—C1164.8 (2)Cl3—B5—C18—C17129.91 (16)
B3—O3—B1—O19.1 (3)Cl2—B5—C18—C17101.87 (17)
B4—O3—B1—O1173.28 (16)O2—B5—C18—C26166.28 (16)
B3—O3—B1—C1171.43 (15)Cl3—B5—C18—C2648.6 (2)
B4—O3—B1—C17.2 (2)Cl2—B5—C18—C2679.6 (2)
B1—O1—B2—O211.4 (3)C18—C17—C19—C20140.0 (2)
B1—O1—B2—C17166.1 (2)B2—C17—C19—C2041.1 (3)
B3—O2—B2—O10.5 (3)C18—C17—C19—C2442.3 (3)
B5—O2—B2—O1177.59 (17)B2—C17—C19—C24136.6 (2)
B3—O2—B2—C17178.46 (16)C24—C19—C20—C211.5 (3)
B5—O2—B2—C174.5 (2)C17—C19—C20—C21179.3 (2)
B1—O3—B3—O21.3 (2)C19—C20—C21—C222.0 (4)
B4—O3—B3—O2160.39 (15)C20—C21—C22—C231.4 (4)
B1—O3—B3—O4116.64 (17)C20—C21—C22—C25179.2 (3)
B4—O3—B3—O445.1 (2)C21—C22—C23—C240.3 (4)
B1—O3—B3—C34128.92 (18)C25—C22—C23—C24179.7 (3)
B4—O3—B3—C3469.4 (2)C22—C23—C24—C190.1 (5)
B2—O2—B3—O36.1 (2)C20—C19—C24—C230.5 (4)
B5—O2—B3—O3177.50 (15)C17—C19—C24—C23178.3 (3)
B2—O2—B3—O4117.92 (17)C17—C18—C26—C27147.1 (2)
B5—O2—B3—O465.7 (2)B5—C18—C26—C2734.6 (3)
B2—O2—B3—C34127.07 (18)C17—C18—C26—C3138.2 (3)
B5—O2—B3—C3449.3 (2)B5—C18—C26—C31140.1 (2)
B6—O4—B3—O3137.01 (15)C31—C26—C27—C280.6 (3)
B7—O4—B3—O319.96 (19)C18—C26—C27—C28175.3 (2)
B6—O4—B3—O2108.82 (16)C26—C27—C28—C291.4 (4)
B7—O4—B3—O294.21 (17)C27—C28—C29—C300.8 (4)
B6—O4—B3—C3412.28 (18)C27—C28—C29—C32178.8 (2)
B7—O4—B3—C34144.68 (15)C28—C29—C30—C310.6 (4)
B8—O5—B4—O3170.58 (17)C32—C29—C30—C31179.7 (3)
B7—O5—B4—O30.6 (2)C29—C30—C31—C261.5 (4)
B8—O5—B4—C280.9 (2)C27—C26—C31—C300.9 (3)
B7—O5—B4—C2109.18 (18)C18—C26—C31—C30174.0 (2)
B8—O5—B4—Cl154.0 (2)O4—B6—C33—C341.2 (2)
B7—O5—B4—Cl1115.96 (15)Cl4—B6—C33—C34174.39 (16)
B1—O3—B4—O5109.57 (15)O4—B6—C33—C35177.81 (17)
B3—O3—B4—O554.9 (2)Cl4—B6—C33—C352.2 (3)
B1—O3—B4—C27.32 (18)C35—C33—C34—C420.2 (3)
B3—O3—B4—C2171.81 (15)B6—C33—C34—C42176.56 (18)
B1—O3—B4—Cl1134.81 (13)C35—C33—C34—B3174.21 (18)
B3—O3—B4—Cl160.70 (19)B6—C33—C34—B39.4 (2)
B2—O2—B5—C189.39 (18)O3—B3—C34—C33128.09 (17)
B3—O2—B5—C18173.65 (16)O2—B3—C34—C33104.45 (18)
B2—O2—B5—Cl3132.13 (14)O4—B3—C34—C3313.6 (2)
B3—O2—B5—Cl350.9 (2)O3—B3—C34—C4257.5 (2)
B2—O2—B5—Cl2107.89 (14)O2—B3—C34—C4269.9 (2)
B3—O2—B5—Cl269.1 (2)O4—B3—C34—C42171.99 (16)
B7—O4—B6—C33145.69 (17)C34—C33—C35—C4059.8 (3)
B3—O4—B6—C337.5 (2)B6—C33—C35—C40116.1 (2)
B7—O4—B6—Cl430.2 (3)C34—C33—C35—C36121.5 (2)
B3—O4—B6—Cl4176.57 (14)B6—C33—C35—C3662.6 (3)
B6—O4—B7—O589.8 (2)C40—C35—C36—C371.8 (3)
B3—O4—B7—O560.44 (18)C33—C35—C36—C37179.5 (2)
B6—O4—B7—C5023.7 (3)C35—C36—C37—C381.7 (4)
B3—O4—B7—C50173.95 (16)C36—C37—C38—C390.2 (4)
B6—O4—B7—Cl5154.03 (15)C36—C37—C38—C41179.6 (2)
B3—O4—B7—Cl555.71 (17)C37—C38—C39—C401.1 (3)
B8—O5—B7—O4123.61 (16)C41—C38—C39—C40179.1 (2)
B4—O5—B7—O448.24 (19)C36—C35—C40—C390.5 (3)
B8—O5—B7—C501.74 (19)C33—C35—C40—C39179.16 (19)
B4—O5—B7—C50173.58 (15)C38—C39—C40—C350.9 (3)
B8—O5—B7—Cl5121.51 (15)C33—C34—C42—C43148.6 (2)
B4—O5—B7—Cl566.64 (18)B3—C34—C42—C4338.1 (3)
B4—O5—B8—C49171.52 (17)C33—C34—C42—C4731.4 (3)
B7—O5—B8—C490.4 (2)B3—C34—C42—C47141.9 (2)
B4—O5—B8—Cl69.4 (3)C47—C42—C43—C443.5 (4)
B7—O5—B8—Cl6179.45 (15)C34—C42—C43—C44176.5 (3)
O1—B1—C1—C2176.7 (2)C42—C43—C44—C452.2 (6)
O3—B1—C1—C23.9 (2)C43—C44—C45—C461.6 (6)
O1—B1—C1—C32.2 (3)C43—C44—C45—C48178.4 (4)
O3—B1—C1—C3177.27 (16)C44—C45—C46—C474.1 (5)
C3—C1—C2—C103.2 (3)C48—C45—C46—C47175.9 (4)
B1—C1—C2—C10175.64 (18)C45—C46—C47—C422.8 (4)
C3—C1—C2—B4177.65 (18)C43—C42—C47—C461.0 (3)
B1—C1—C2—B41.2 (2)C34—C42—C47—C46179.0 (2)
O5—B4—C2—C1103.03 (18)O5—B8—C49—C501.4 (2)
O3—B4—C2—C15.2 (2)Cl6—B8—C49—C50177.62 (17)
Cl1—B4—C2—C1126.97 (16)O5—B8—C49—C51179.60 (18)
O5—B4—C2—C1071.6 (2)Cl6—B8—C49—C511.4 (3)
O3—B4—C2—C10179.80 (16)C51—C49—C50—C589.4 (3)
Cl1—B4—C2—C1058.4 (2)B8—C49—C50—C58169.56 (19)
C2—C1—C3—C4139.2 (2)C51—C49—C50—B7178.56 (19)
B1—C1—C3—C439.5 (3)B8—C49—C50—B72.5 (2)
C2—C1—C3—C841.1 (3)O4—B7—C50—C49110.42 (19)
B1—C1—C3—C8140.3 (2)O5—B7—C50—C492.7 (2)
C8—C3—C4—C50.9 (3)Cl5—B7—C50—C49120.96 (16)
C1—C3—C4—C5179.3 (2)O4—B7—C50—C5877.1 (2)
C3—C4—C5—C61.5 (4)O5—B7—C50—C58169.80 (16)
C4—C5—C6—C71.1 (4)Cl5—B7—C50—C5851.5 (2)
C4—C5—C6—C9177.9 (2)C50—C49—C51—C56120.7 (2)
C5—C6—C7—C80.2 (4)B8—C49—C51—C5658.2 (3)
C9—C6—C7—C8178.9 (2)C50—C49—C51—C5259.5 (3)
C6—C7—C8—C30.4 (4)B8—C49—C51—C52121.7 (2)
C4—C3—C8—C70.0 (3)C56—C51—C52—C531.1 (3)
C1—C3—C8—C7179.7 (2)C49—C51—C52—C53179.0 (2)
C1—C2—C10—C1555.9 (3)C51—C52—C53—C540.9 (4)
B4—C2—C10—C15118.0 (2)C52—C53—C54—C550.4 (4)
C1—C2—C10—C11125.5 (2)C52—C53—C54—C57180.0 (3)
B4—C2—C10—C1160.6 (3)C53—C54—C55—C560.3 (4)
C15—C10—C11—C121.6 (3)C57—C54—C55—C56179.9 (3)
C2—C10—C11—C12177.0 (2)C52—C51—C56—C551.0 (3)
C10—C11—C12—C130.7 (4)C49—C51—C56—C55179.2 (2)
C11—C12—C13—C141.7 (4)C54—C55—C56—C510.5 (4)
C11—C12—C13—C16178.6 (3)C49—C50—C58—C59167.0 (2)
C12—C13—C14—C150.4 (4)B7—C50—C58—C5922.0 (3)
C16—C13—C14—C15179.8 (3)C49—C50—C58—C6316.3 (3)
C11—C10—C15—C142.9 (3)B7—C50—C58—C63154.8 (2)
C2—C10—C15—C14175.8 (2)C63—C58—C59—C602.9 (3)
C13—C14—C15—C101.9 (4)C50—C58—C59—C60179.85 (18)
O1—B2—C17—C18174.3 (2)C58—C59—C60—C611.1 (3)
O2—B2—C17—C183.4 (2)C59—C60—C61—C620.9 (3)
O1—B2—C17—C196.7 (3)C59—C60—C61—C64178.7 (2)
O2—B2—C17—C19175.67 (18)C60—C61—C62—C631.0 (4)
C19—C17—C18—C2612.6 (3)C64—C61—C62—C63178.6 (2)
B2—C17—C18—C26168.36 (18)C61—C62—C63—C580.8 (4)
C19—C17—C18—B5168.91 (19)C59—C58—C63—C622.7 (3)
B2—C17—C18—B510.1 (2)C50—C58—C63—C62179.6 (2)

Experimental details

Crystal data
Chemical formulaC64H56B8Cl6O5·5(CH2Cl2)
Mr1628.90
Crystal system, space groupTriclinic, 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)
V3)4056.3 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.59
Crystal size (mm)0.45 × 0.32 × 0.31
Data collection
DiffractometerCCD area detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1999)
Tmin, Tmax0.896, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
68074, 25625, 17850
Rint0.034
(sin θ/λ)max1)0.725
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.063, 0.214, 1.17
No. of reflections25625
No. of parameters841
H-atom treatmentOnly H-atom displacement parameters refined
Δρmax, Δρmin (e Å3)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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