Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270107026170/fa3095sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270107026170/fa3095Isup2.hkl |
CCDC reference: 655495
A solution of 1L-3,4-bis(O-diphenylphosphino)-1,2,5,6-tetra-O-methyl-chiro-inositol (122 mg, O.20 mmol) in tetrahydrofuran (5 ml) was added dropwise to a solution of (RhCODCl)2 (49 mg, 0.10 mmol) in tetrahydrofuran (5 ml). The reaction mixture was stirred at room temperature for 17 h. AgBF4 (0.039 g, 0.2 mmol) was added and the reaction mixture stirred for 2 h. Filtration and removal of the solvent yielded an orange solid. Crystallization from CHCl3/pentane yielded the pure title compound as a CHCl3 solvate (0.078 g, 76%). 31P NMR (CDCl3): 134.8 (JRh—P = 178 Hz). Analysis calculated for C43H51BCl3F4O6P2Rh: C 50.54, H 5.03%; found: C 50.44, H 5.00%.
The disorder of the chloroform atoms was modelled using two-position linked atoms for one H and one Cl atom in each of the two molecules; H atoms were positioned (C—H = 1.03 Å) and fixed in the final refinement cycles with one common Uiso value. Identical anisotropic displacement parameters were used for disordered chloroform atoms Cl8A and Cl8B and for Cl7Aand Cl7B. The final major occupancies for the linked atoms were 0.564 (10) and 0.534 (6) for the C7 and C8 molecules, respectively. All other C-bound H atoms were constrained to their expected geometries (C—H = 0.95–1.00 Å) and were refined with Uiso(H) values of 1.2 or 1.5 times Ueq of their parent C atom. Only selected non-H atoms were refined with anisotropic thermal parameters in order to maintain a reasonable data/parameter ratio. There is a strong suggestion of the presence of a minor crystal fragment contributing to some of the data. The worst fit data (the top 35 reflections) have Fo >> Fc; removal of data for which Fo > 1.5Fc (830 data with R around 20%) improved agreement R1 (0.064 to 0.055) but with only insigificant changes in the model. Given no definitive experimental evidence for this, the full collected data results are presented here.
Data collection: SMART (Siemens, 2001); cell refinement: SMART; data reduction: SAINT (Siemens, 2001) and SADABS (Sheldrick, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.
[Rh(C8H12)(C34H38O6P2)]BF4·CHCl3 | F(000) = 2096 |
Mr = 1021.85 | Dx = 1.502 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 6137 reflections |
a = 9.3231 (17) Å | θ = 2.2–26.2° |
b = 26.611 (6) Å | µ = 0.69 mm−1 |
c = 18.218 (4) Å | T = 158 K |
β = 91.596 (7)° | Plate, orange |
V = 4518.0 (16) Å3 | 0.9 × 0.4 × 0.04 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 15833 independent reflections |
Radiation source: fine-focus sealed tube | 13832 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 8.192 pixels mm-1 | θmax = 26.4°, θmin = 2.2° |
ϕ and ω scans | h = −4→10 |
Absorption correction: multi-scan (Blessing, 1995) | k = −33→33 |
Tmin = 0.785, Tmax = 0.973 | l = −22→21 |
19306 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0443P)2 + 25.1837P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.004 |
15833 reflections | Δρmax = 0.83 e Å−3 |
645 parameters | Δρmin = −1.48 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 6332 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (3) |
[Rh(C8H12)(C34H38O6P2)]BF4·CHCl3 | V = 4518.0 (16) Å3 |
Mr = 1021.85 | Z = 4 |
Monoclinic, P21 | Mo Kα radiation |
a = 9.3231 (17) Å | µ = 0.69 mm−1 |
b = 26.611 (6) Å | T = 158 K |
c = 18.218 (4) Å | 0.9 × 0.4 × 0.04 mm |
β = 91.596 (7)° |
Bruker SMART CCD area-detector diffractometer | 15833 independent reflections |
Absorption correction: multi-scan (Blessing, 1995) | 13832 reflections with I > 2σ(I) |
Tmin = 0.785, Tmax = 0.973 | Rint = 0.026 |
19306 measured reflections |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.150 | w = 1/[σ2(Fo2) + (0.0443P)2 + 25.1837P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | Δρmax = 0.83 e Å−3 |
15833 reflections | Δρmin = −1.48 e Å−3 |
645 parameters | Absolute structure: Flack (1983), 6332 Friedel pairs |
1 restraint | Absolute structure parameter: 0.05 (3) |
Experimental. Crystal decay was monitored by repeating the initial 10 frames at the end of the data collection and analyzing duplicate reflections. The standard 0.8 mm diameter collimator was used. 1L-3,4-bis(O-diphenylphosphino)-1,2,5,6-tetra-O-methyl-chiro- inositol Rhodium cyclo-octadiene tetrafluoroborate). |
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 | Occ. (<1) | |
Rh1 | 0.79986 (6) | 0.16998 (2) | 0.56130 (3) | 0.02033 (13) | |
P1 | 0.7879 (2) | 0.16528 (7) | 0.43676 (9) | 0.0190 (4) | |
P2 | 0.5596 (2) | 0.17944 (7) | 0.56520 (10) | 0.0182 (4) | |
Cl71 | 0.7359 (6) | −0.08922 (15) | 0.6771 (3) | 0.1038 (14) | |
Cl72 | 0.9682 (8) | −0.0222 (2) | 0.6549 (4) | 0.169 (3) | |
Cl81 | 0.7140 (5) | 0.04991 (14) | 0.8207 (2) | 0.0986 (14) | |
Cl82 | 0.9926 (8) | 0.0106 (3) | 0.8583 (3) | 0.162 (3) | |
B1 | 0.8989 (13) | 0.1007 (4) | 0.0609 (6) | 0.038 (2) | |
B2 | 0.9632 (14) | 0.3830 (4) | 0.5478 (6) | 0.042 (3) | |
F11 | 0.9317 (12) | 0.0881 (4) | 0.1306 (4) | 0.120 (4) | |
F12 | 0.9946 (10) | 0.0780 (3) | 0.0125 (5) | 0.095 (3) | |
F13 | 0.9057 (8) | 0.1513 (2) | 0.0499 (4) | 0.0635 (18) | |
F14 | 0.7679 (8) | 0.0816 (2) | 0.0424 (4) | 0.069 (2) | |
F21 | 0.9553 (8) | 0.3308 (2) | 0.5526 (4) | 0.071 (2) | |
F22 | 0.8930 (9) | 0.3989 (3) | 0.4854 (4) | 0.079 (2) | |
F23 | 1.1047 (8) | 0.3969 (2) | 0.5454 (5) | 0.073 (2) | |
F24 | 0.9002 (10) | 0.4062 (3) | 0.6054 (5) | 0.097 (3) | |
O1 | 0.6387 (6) | 0.17863 (18) | 0.3941 (2) | 0.0226 (11)* | |
O2 | 0.4517 (6) | 0.14528 (18) | 0.5155 (3) | 0.0251 (11)* | |
O23 | 0.3797 (7) | 0.0456 (2) | 0.5082 (3) | 0.0349 (13)* | |
O24 | 0.5174 (7) | 0.0198 (2) | 0.3702 (3) | 0.0358 (14)* | |
O25 | 0.2570 (7) | 0.1107 (2) | 0.3073 (3) | 0.0315 (13)* | |
O26 | 0.5277 (6) | 0.15250 (18) | 0.2582 (3) | 0.0270 (12)* | |
C11 | 0.8148 (10) | 0.1993 (3) | 0.6775 (4) | 0.0264 (17)* | |
H11 | 0.7182 | 0.2105 | 0.6742 | 0.032* | |
C12 | 0.8350 (10) | 0.1490 (3) | 0.6788 (4) | 0.0304 (19)* | |
H12 | 0.7534 | 0.1279 | 0.6720 | 0.037* | |
C13 | 0.9817 (10) | 0.1241 (3) | 0.6905 (5) | 0.038 (2)* | |
H13A | 1.0439 | 0.1468 | 0.7204 | 0.045* | |
H13B | 0.9693 | 0.0927 | 0.7188 | 0.045* | |
C14 | 1.0572 (11) | 0.1117 (3) | 0.6195 (5) | 0.037 (2)* | |
H14A | 1.1616 | 0.1090 | 0.6305 | 0.044* | |
H14B | 1.0236 | 0.0784 | 0.6019 | 0.044* | |
C15 | 1.0342 (10) | 0.1484 (3) | 0.5602 (5) | 0.0292 (18)* | |
H15 | 1.0209 | 0.1351 | 0.5121 | 0.035* | |
C16 | 1.0296 (10) | 0.2006 (3) | 0.5666 (4) | 0.0264 (17)* | |
H16 | 1.0051 | 0.2200 | 0.5244 | 0.032* | |
C17 | 1.0622 (10) | 0.2275 (3) | 0.6386 (4) | 0.0329 (19)* | |
H17A | 1.1265 | 0.2062 | 0.6696 | 0.040* | |
H17B | 1.1137 | 0.2592 | 0.6284 | 0.040* | |
C18 | 0.9289 (10) | 0.2395 (3) | 0.6806 (5) | 0.0352 (19)* | |
H18A | 0.9571 | 0.2455 | 0.7327 | 0.042* | |
H18B | 0.8870 | 0.2711 | 0.6610 | 0.042* | |
C21 | 0.5121 (8) | 0.1466 (3) | 0.3861 (4) | 0.0192 (14)* | |
H21 | 0.4272 | 0.1694 | 0.3812 | 0.023* | |
C22 | 0.4910 (8) | 0.1149 (3) | 0.4545 (4) | 0.0208 (15)* | |
H22 | 0.5827 | 0.0971 | 0.4672 | 0.025* | |
C23 | 0.3711 (9) | 0.0763 (3) | 0.4454 (4) | 0.0232 (15)* | |
H23 | 0.2768 | 0.0942 | 0.4445 | 0.028* | |
C27 | 0.2550 (11) | 0.0153 (4) | 0.5183 (5) | 0.043 (2) | |
H27A | 0.2688 | −0.0054 | 0.5624 | 0.065* | |
H27B | 0.2393 | −0.0064 | 0.4754 | 0.065* | |
H27C | 0.1713 | 0.0371 | 0.5241 | 0.065* | |
C24 | 0.3843 (9) | 0.0471 (3) | 0.3737 (4) | 0.0294 (17)* | |
H24 | 0.3020 | 0.0232 | 0.3679 | 0.035* | |
C28 | 0.5146 (14) | −0.0298 (3) | 0.3971 (7) | 0.064 (3) | |
H28A | 0.6091 | −0.0453 | 0.3917 | 0.096* | |
H28B | 0.4424 | −0.0493 | 0.3691 | 0.096* | |
H28C | 0.4902 | −0.0294 | 0.4490 | 0.096* | |
C25 | 0.3846 (9) | 0.0828 (3) | 0.3084 (4) | 0.0238 (15)* | |
H25 | 0.3900 | 0.0629 | 0.2620 | 0.029* | |
C29 | 0.2057 (9) | 0.1239 (4) | 0.2364 (4) | 0.036 (2) | |
H29A | 0.1170 | 0.1434 | 0.2401 | 0.055* | |
H29B | 0.1864 | 0.0933 | 0.2078 | 0.055* | |
H29C | 0.2781 | 0.1441 | 0.2119 | 0.055* | |
C26 | 0.5183 (9) | 0.1173 (3) | 0.3163 (4) | 0.0225 (15)* | |
H26 | 0.6067 | 0.0959 | 0.3177 | 0.027* | |
C30 | 0.5789 (11) | 0.1324 (3) | 0.1925 (4) | 0.036 (2) | |
H30A | 0.5807 | 0.1588 | 0.1550 | 0.055* | |
H30B | 0.5155 | 0.1051 | 0.1756 | 0.055* | |
H30C | 0.6761 | 0.1193 | 0.2011 | 0.055* | |
C111 | 0.8450 (9) | 0.1052 (3) | 0.4003 (4) | 0.0249 (16)* | |
C112 | 0.8570 (9) | 0.0641 (3) | 0.4472 (4) | 0.0299 (17)* | |
H112 | 0.8394 | 0.0682 | 0.4980 | 0.036* | |
C113 | 0.8946 (11) | 0.0171 (4) | 0.4205 (5) | 0.043 (2)* | |
H113 | 0.9029 | −0.0109 | 0.4526 | 0.051* | |
C114 | 0.9196 (11) | 0.0118 (4) | 0.3462 (5) | 0.042 (2)* | |
H114 | 0.9432 | −0.0203 | 0.3274 | 0.051* | |
C115 | 0.9108 (10) | 0.0529 (3) | 0.2985 (5) | 0.038 (2)* | |
H115 | 0.9305 | 0.0488 | 0.2480 | 0.046* | |
C116 | 0.8731 (9) | 0.0996 (3) | 0.3252 (4) | 0.0301 (18)* | |
H116 | 0.8663 | 0.1277 | 0.2931 | 0.036* | |
C121 | 0.9026 (9) | 0.2113 (3) | 0.3961 (4) | 0.0224 (15)* | |
C122 | 1.0417 (9) | 0.1990 (3) | 0.3766 (4) | 0.0275 (17)* | |
H122 | 1.0720 | 0.1649 | 0.3772 | 0.033* | |
C123 | 1.1377 (11) | 0.2373 (3) | 0.3559 (5) | 0.040 (2)* | |
H123 | 1.2330 | 0.2291 | 0.3432 | 0.048* | |
C124 | 1.0926 (12) | 0.2864 (4) | 0.3541 (5) | 0.046 (2)* | |
H124 | 1.1565 | 0.3122 | 0.3400 | 0.055* | |
C125 | 0.9545 (10) | 0.2983 (3) | 0.3729 (4) | 0.0357 (19)* | |
H125 | 0.9253 | 0.3325 | 0.3716 | 0.043* | |
C126 | 0.8564 (10) | 0.2620 (3) | 0.3936 (4) | 0.0287 (17)* | |
H126 | 0.7613 | 0.2710 | 0.4058 | 0.034* | |
C211 | 0.4748 (7) | 0.1683 (3) | 0.6509 (3) | 0.0204 (13)* | |
C212 | 0.4313 (9) | 0.2070 (3) | 0.6986 (4) | 0.0255 (16)* | |
H212 | 0.4429 | 0.2409 | 0.6838 | 0.031* | |
C213 | 0.3716 (10) | 0.1971 (3) | 0.7672 (5) | 0.0346 (19)* | |
H213 | 0.3414 | 0.2239 | 0.7975 | 0.042* | |
C214 | 0.3576 (11) | 0.1480 (3) | 0.7896 (5) | 0.040 (2)* | |
H214 | 0.3193 | 0.1404 | 0.8361 | 0.048* | |
C215 | 0.4018 (12) | 0.1085 (4) | 0.7415 (5) | 0.046 (2)* | |
H215 | 0.3911 | 0.0745 | 0.7565 | 0.056* | |
C216 | 0.4580 (10) | 0.1183 (3) | 0.6760 (5) | 0.0326 (19)* | |
H216 | 0.4870 | 0.0912 | 0.6459 | 0.039* | |
C221 | 0.5097 (9) | 0.2433 (3) | 0.5414 (4) | 0.0274 (17)* | |
C222 | 0.6146 (10) | 0.2814 (3) | 0.5416 (4) | 0.0274 (17)* | |
H222 | 0.7121 | 0.2737 | 0.5531 | 0.033* | |
C223 | 0.5738 (10) | 0.3309 (3) | 0.5247 (5) | 0.035 (2)* | |
H223 | 0.6433 | 0.3570 | 0.5263 | 0.042* | |
C224 | 0.4342 (10) | 0.3416 (3) | 0.5060 (4) | 0.0331 (18)* | |
H224 | 0.4078 | 0.3751 | 0.4936 | 0.040* | |
C225 | 0.3305 (10) | 0.3040 (4) | 0.5049 (4) | 0.0354 (18)* | |
H225 | 0.2335 | 0.3122 | 0.4928 | 0.042* | |
C226 | 0.3677 (9) | 0.2548 (3) | 0.5215 (4) | 0.0267 (17)* | |
H226 | 0.2971 | 0.2291 | 0.5193 | 0.032* | |
Rh2 | 0.08715 (6) | 0.30622 (2) | 0.05804 (3) | 0.02121 (13) | |
P3 | 0.0865 (2) | 0.31006 (8) | −0.06624 (9) | 0.0189 (4) | |
P4 | 0.3257 (2) | 0.29197 (7) | 0.06169 (10) | 0.0206 (4) | |
O3 | 0.2297 (6) | 0.29477 (17) | −0.1100 (3) | 0.0232 (11)* | |
O4 | 0.4324 (6) | 0.32300 (18) | 0.0098 (3) | 0.0273 (12)* | |
O33 | 0.5282 (6) | 0.4199 (2) | 0.0068 (3) | 0.0319 (13)* | |
O34 | 0.3799 (7) | 0.4545 (2) | −0.1177 (3) | 0.0328 (13)* | |
O35 | 0.6005 (6) | 0.3578 (2) | −0.1984 (3) | 0.0298 (12)* | |
O36 | 0.3114 (6) | 0.32666 (19) | −0.2456 (3) | 0.0291 (12)* | |
C41 | 0.0759 (9) | 0.2769 (3) | 0.1748 (4) | 0.0251 (17)* | |
H41 | 0.1683 | 0.2623 | 0.1707 | 0.030* | |
C42 | 0.0700 (10) | 0.3275 (3) | 0.1769 (4) | 0.0263 (17)* | |
H42 | 0.1575 | 0.3452 | 0.1713 | 0.032* | |
C43 | −0.0647 (10) | 0.3589 (3) | 0.1876 (5) | 0.0334 (19)* | |
H43A | −0.1308 | 0.3395 | 0.2185 | 0.040* | |
H43B | −0.0372 | 0.3897 | 0.2151 | 0.040* | |
C44 | −0.1453 (11) | 0.3743 (3) | 0.1181 (5) | 0.037 (2)* | |
H44A | −0.1037 | 0.4060 | 0.0999 | 0.044* | |
H44B | −0.2465 | 0.3811 | 0.1299 | 0.044* | |
C45 | −0.1421 (9) | 0.3353 (3) | 0.0572 (4) | 0.0246 (17)* | |
H45 | −0.1329 | 0.3475 | 0.0086 | 0.030* | |
C46 | −0.1509 (10) | 0.2857 (3) | 0.0652 (5) | 0.035 (2)* | |
H46 | −0.1330 | 0.2654 | 0.0236 | 0.042* | |
C47 | −0.1873 (10) | 0.2591 (3) | 0.1361 (4) | 0.0327 (18)* | |
H47A | −0.2488 | 0.2296 | 0.1248 | 0.039* | |
H47B | −0.2417 | 0.2822 | 0.1676 | 0.039* | |
C48 | −0.0483 (9) | 0.2414 (3) | 0.1783 (4) | 0.0305 (18)* | |
H48A | −0.0712 | 0.2362 | 0.2305 | 0.037* | |
H48B | −0.0189 | 0.2086 | 0.1582 | 0.037* | |
C31 | 0.3540 (9) | 0.3259 (3) | −0.1172 (4) | 0.0240 (16)* | |
H31 | 0.4362 | 0.3025 | −0.1248 | 0.029* | |
C32 | 0.3924 (9) | 0.3561 (3) | −0.0486 (4) | 0.0217 (15)* | |
H32 | 0.3071 | 0.3762 | −0.0342 | 0.026* | |
C33 | 0.5192 (9) | 0.3913 (3) | −0.0587 (4) | 0.0244 (16)* | |
H33 | 0.6086 | 0.3709 | −0.0629 | 0.029* | |
C37 | 0.6370 (11) | 0.4574 (3) | 0.0078 (5) | 0.042 (2) | |
H37A | 0.6358 | 0.4756 | 0.0546 | 0.063* | |
H37B | 0.6193 | 0.4809 | −0.0327 | 0.063* | |
H37C | 0.7309 | 0.4414 | 0.0024 | 0.063* | |
C34 | 0.5004 (9) | 0.4240 (3) | −0.1269 (4) | 0.0239 (15)* | |
H34 | 0.5875 | 0.4454 | −0.1331 | 0.029* | |
C38 | 0.3697 (14) | 0.4972 (4) | −0.1641 (7) | 0.065 (3) | |
H38A | 0.2820 | 0.5159 | −0.1537 | 0.098* | |
H38B | 0.3666 | 0.4863 | −0.2155 | 0.098* | |
H38C | 0.4533 | 0.5189 | −0.1552 | 0.098* | |
C35 | 0.4783 (9) | 0.3893 (3) | −0.1940 (4) | 0.0237 (15)* | |
H35 | 0.4693 | 0.4102 | −0.2395 | 0.028* | |
C39 | 0.6391 (11) | 0.3443 (4) | −0.2718 (5) | 0.040 (2) | |
H39A | 0.7248 | 0.3229 | −0.2697 | 0.060* | |
H39B | 0.6592 | 0.3748 | −0.2998 | 0.060* | |
H39C | 0.5597 | 0.3259 | −0.2958 | 0.060* | |
C36 | 0.3433 (8) | 0.3590 (3) | −0.1856 (4) | 0.0208 (14)* | |
H36 | 0.2611 | 0.3827 | −0.1801 | 0.025* | |
C40 | 0.2590 (11) | 0.3526 (3) | −0.3098 (4) | 0.039 (2) | |
H40A | 0.2391 | 0.3283 | −0.3492 | 0.058* | |
H40B | 0.3313 | 0.3767 | −0.3256 | 0.058* | |
H40C | 0.1705 | 0.3706 | −0.2985 | 0.058* | |
C311 | 0.0235 (9) | 0.3696 (3) | −0.1056 (4) | 0.0234 (15)* | |
C312 | 0.0305 (10) | 0.4123 (3) | −0.0621 (4) | 0.0315 (18)* | |
H312 | 0.0632 | 0.4100 | −0.0123 | 0.038* | |
C313 | −0.0104 (11) | 0.4589 (4) | −0.0915 (5) | 0.044 (2)* | |
H313 | −0.0047 | 0.4885 | −0.0625 | 0.053* | |
C314 | −0.0593 (12) | 0.4610 (4) | −0.1635 (5) | 0.046 (2)* | |
H314 | −0.0910 | 0.4923 | −0.1831 | 0.055* | |
C315 | −0.0636 (11) | 0.4191 (3) | −0.2079 (5) | 0.042 (2)* | |
H315 | −0.0954 | 0.4218 | −0.2578 | 0.050* | |
C316 | −0.0214 (10) | 0.3731 (3) | −0.1795 (4) | 0.0307 (18)* | |
H316 | −0.0228 | 0.3440 | −0.2098 | 0.037* | |
C321 | −0.0304 (8) | 0.2626 (3) | −0.1047 (4) | 0.0217 (15)* | |
C322 | −0.1741 (9) | 0.2731 (3) | −0.1235 (4) | 0.0268 (16)* | |
H322 | −0.2068 | 0.3069 | −0.1229 | 0.032* | |
C323 | −0.2696 (10) | 0.2351 (3) | −0.1431 (4) | 0.0343 (19)* | |
H323 | −0.3672 | 0.2425 | −0.1547 | 0.041* | |
C324 | −0.2196 (10) | 0.1859 (3) | −0.1454 (5) | 0.0341 (19)* | |
H324 | −0.2837 | 0.1596 | −0.1593 | 0.041* | |
C325 | −0.0778 (9) | 0.1746 (3) | −0.1275 (4) | 0.0350 (18)* | |
H325 | −0.0459 | 0.1407 | −0.1286 | 0.042* | |
C326 | 0.0176 (10) | 0.2125 (3) | −0.1082 (4) | 0.0291 (17)* | |
H326 | 0.1153 | 0.2047 | −0.0973 | 0.035* | |
C411 | 0.4206 (8) | 0.3030 (3) | 0.1489 (3) | 0.0209 (13)* | |
C412 | 0.4654 (10) | 0.3524 (3) | 0.1646 (4) | 0.0306 (18)* | |
H412 | 0.4506 | 0.3784 | 0.1296 | 0.037* | |
C413 | 0.5318 (10) | 0.3625 (3) | 0.2323 (4) | 0.0340 (19)* | |
H413 | 0.5626 | 0.3957 | 0.2435 | 0.041* | |
C414 | 0.5535 (10) | 0.3247 (3) | 0.2837 (5) | 0.0355 (19)* | |
H414 | 0.5969 | 0.3321 | 0.3302 | 0.043* | |
C415 | 0.5115 (10) | 0.2758 (3) | 0.2669 (5) | 0.0332 (18)* | |
H415 | 0.5269 | 0.2496 | 0.3017 | 0.040* | |
C416 | 0.4478 (8) | 0.2654 (3) | 0.1997 (4) | 0.0218 (15)* | |
H416 | 0.4218 | 0.2318 | 0.1880 | 0.026* | |
C421 | 0.3663 (9) | 0.2276 (3) | 0.0387 (4) | 0.0247 (16)* | |
C422 | 0.2635 (10) | 0.1906 (3) | 0.0437 (4) | 0.0300 (17)* | |
H422 | 0.1697 | 0.1987 | 0.0589 | 0.036* | |
C423 | 0.2984 (11) | 0.1411 (4) | 0.0261 (5) | 0.041 (2)* | |
H423 | 0.2273 | 0.1157 | 0.0292 | 0.050* | |
C424 | 0.4348 (10) | 0.1285 (3) | 0.0042 (5) | 0.0362 (19)* | |
H424 | 0.4577 | 0.0946 | −0.0071 | 0.043* | |
C425 | 0.5361 (10) | 0.1652 (3) | −0.0011 (4) | 0.0379 (19)* | |
H425 | 0.6295 | 0.1567 | −0.0166 | 0.045* | |
C426 | 0.5050 (9) | 0.2151 (3) | 0.0157 (4) | 0.0285 (17)* | |
H426 | 0.5765 | 0.2403 | 0.0118 | 0.034* | |
C7 | 0.816 (2) | −0.0490 (5) | 0.6177 (8) | 0.090 (5) | |
C8 | 0.8153 (17) | 0.0220 (4) | 0.8885 (7) | 0.072 (4) | |
Cl7A | 0.6659 (10) | −0.0086 (3) | 0.5805 (5) | 0.0881 (16)* | 0.564 (10) |
Cl8A | 0.7082 (9) | −0.0225 (2) | 0.9321 (4) | 0.0829 (17) | 0.534 (6) |
H7A | 0.8471 | −0.0705 | 0.5737 | 0.11 (4)* | 0.564 (10) |
H8A | 0.8273 | 0.0498 | 0.9275 | 0.11 (4)* | 0.534 (6) |
Cl7B | 0.7224 (13) | 0.0063 (4) | 0.6036 (6) | 0.0881 (16)* | 0.436 (10) |
Cl8B | 0.7818 (10) | −0.0464 (3) | 0.8923 (5) | 0.0829 (17) | 0.466 (6) |
H7B | 0.8352 | −0.0665 | 0.5681 | 0.11 (4)* | 0.436 (10) |
H8B | 0.8101 | 0.0400 | 0.9385 | 0.11 (4)* | 0.466 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Rh1 | 0.0163 (3) | 0.0237 (3) | 0.0208 (3) | 0.0020 (2) | −0.0024 (2) | −0.0020 (2) |
P1 | 0.0154 (11) | 0.0205 (9) | 0.0209 (8) | 0.0018 (7) | −0.0004 (7) | 0.0010 (8) |
P2 | 0.0098 (11) | 0.0242 (11) | 0.0206 (8) | −0.0008 (7) | −0.0004 (7) | −0.0023 (7) |
Cl71 | 0.121 (4) | 0.069 (2) | 0.123 (3) | −0.003 (2) | 0.035 (3) | 0.039 (2) |
Cl72 | 0.190 (7) | 0.132 (5) | 0.186 (6) | −0.085 (5) | 0.051 (5) | −0.024 (4) |
Cl81 | 0.107 (3) | 0.074 (2) | 0.113 (3) | −0.010 (2) | −0.029 (3) | 0.033 (2) |
Cl82 | 0.155 (6) | 0.198 (6) | 0.134 (5) | 0.099 (5) | 0.020 (4) | 0.003 (4) |
B1 | 0.030 (7) | 0.044 (6) | 0.039 (5) | −0.007 (4) | 0.004 (4) | 0.001 (4) |
B2 | 0.047 (8) | 0.034 (5) | 0.046 (6) | −0.008 (5) | −0.004 (5) | −0.001 (5) |
F11 | 0.168 (10) | 0.130 (8) | 0.059 (5) | −0.044 (7) | −0.052 (6) | 0.040 (5) |
F12 | 0.086 (7) | 0.069 (5) | 0.132 (7) | −0.012 (4) | 0.050 (5) | −0.027 (5) |
F13 | 0.078 (5) | 0.038 (3) | 0.075 (4) | −0.006 (3) | 0.001 (4) | −0.004 (3) |
F14 | 0.055 (5) | 0.053 (4) | 0.098 (5) | −0.004 (3) | −0.007 (4) | −0.002 (4) |
F21 | 0.076 (6) | 0.035 (3) | 0.100 (5) | −0.009 (3) | −0.020 (4) | 0.018 (3) |
F22 | 0.105 (7) | 0.061 (4) | 0.069 (4) | 0.023 (4) | −0.031 (4) | 0.005 (3) |
F23 | 0.056 (5) | 0.039 (3) | 0.126 (6) | −0.004 (3) | 0.002 (4) | 0.008 (4) |
F24 | 0.101 (8) | 0.105 (6) | 0.087 (6) | −0.023 (5) | 0.031 (5) | −0.046 (5) |
C27 | 0.041 (7) | 0.039 (5) | 0.051 (6) | −0.014 (4) | 0.016 (4) | −0.002 (4) |
C28 | 0.090 (10) | 0.022 (5) | 0.082 (8) | 0.019 (5) | 0.026 (7) | −0.002 (5) |
C29 | 0.019 (5) | 0.065 (6) | 0.025 (4) | 0.002 (4) | −0.005 (3) | 0.008 (4) |
C30 | 0.040 (6) | 0.045 (5) | 0.024 (4) | −0.004 (4) | −0.001 (4) | −0.004 (4) |
Rh2 | 0.0153 (3) | 0.0270 (3) | 0.0212 (3) | −0.0017 (2) | −0.0020 (2) | 0.0028 (2) |
P3 | 0.0169 (11) | 0.0196 (9) | 0.0201 (8) | −0.0020 (8) | −0.0017 (6) | 0.0032 (8) |
P4 | 0.0157 (12) | 0.0242 (10) | 0.0217 (9) | −0.0017 (7) | −0.0021 (7) | 0.0047 (7) |
C37 | 0.048 (7) | 0.031 (5) | 0.047 (5) | −0.018 (4) | −0.010 (4) | 0.000 (4) |
C38 | 0.076 (10) | 0.049 (6) | 0.071 (8) | 0.017 (6) | 0.016 (6) | 0.028 (6) |
C39 | 0.040 (7) | 0.048 (5) | 0.031 (4) | −0.003 (4) | 0.014 (4) | −0.003 (4) |
C40 | 0.050 (7) | 0.043 (5) | 0.023 (4) | −0.004 (4) | −0.007 (4) | 0.002 (4) |
C7 | 0.127 (15) | 0.048 (7) | 0.095 (11) | 0.003 (8) | 0.043 (10) | 0.011 (7) |
C8 | 0.112 (12) | 0.046 (6) | 0.058 (7) | −0.023 (7) | −0.013 (7) | 0.010 (5) |
Cl8A | 0.096 (5) | 0.060 (3) | 0.091 (4) | −0.014 (3) | −0.018 (3) | 0.035 (3) |
Cl8B | 0.096 (5) | 0.060 (3) | 0.091 (4) | −0.014 (3) | −0.018 (3) | 0.035 (3) |
Rh1—C12 | 2.227 (8) | C225—H225 | 0.9500 |
Rh1—C11 | 2.256 (8) | C226—H226 | 0.9500 |
Rh1—P2 | 2.257 (2) | Rh2—C42 | 2.249 (8) |
Rh1—C15 | 2.259 (9) | Rh2—P4 | 2.255 (2) |
Rh1—P1 | 2.2719 (18) | Rh2—P3 | 2.2662 (18) |
Rh1—C16 | 2.291 (9) | Rh2—C41 | 2.271 (8) |
P1—O1 | 1.613 (5) | Rh2—C45 | 2.273 (8) |
P1—C121 | 1.799 (8) | Rh2—C46 | 2.293 (10) |
P1—C111 | 1.816 (8) | P3—O3 | 1.625 (6) |
P2—O2 | 1.614 (5) | P3—C321 | 1.797 (7) |
P2—C211 | 1.795 (7) | P3—C311 | 1.830 (7) |
P2—C221 | 1.811 (8) | P4—O4 | 1.618 (6) |
Cl71—C7 | 1.707 (14) | P4—C421 | 1.805 (8) |
Cl72—C7 | 1.713 (19) | P4—C411 | 1.820 (7) |
Cl81—C8 | 1.705 (13) | O3—C31 | 1.433 (9) |
Cl82—C8 | 1.783 (17) | O4—C32 | 1.423 (8) |
B1—F11 | 1.339 (12) | O33—C33 | 1.415 (9) |
B1—F14 | 1.356 (13) | O33—C37 | 1.422 (10) |
B1—F13 | 1.362 (12) | O34—C34 | 1.400 (9) |
B1—F12 | 1.407 (13) | O34—C38 | 1.418 (11) |
B2—F22 | 1.363 (13) | O35—C35 | 1.419 (9) |
B2—F24 | 1.365 (14) | O35—C39 | 1.440 (10) |
B2—F23 | 1.373 (14) | O36—C36 | 1.416 (8) |
B2—F21 | 1.393 (12) | O36—C40 | 1.433 (9) |
O1—C21 | 1.460 (9) | C41—C42 | 1.348 (10) |
O2—C22 | 1.431 (8) | C41—C48 | 1.497 (11) |
O23—C23 | 1.408 (9) | C41—H41 | 0.9500 |
O23—C27 | 1.430 (11) | C42—C43 | 1.525 (12) |
O24—C28 | 1.409 (11) | C42—H42 | 0.9500 |
O24—C24 | 1.441 (10) | C43—C44 | 1.511 (12) |
O25—C25 | 1.402 (10) | C43—H43A | 0.9900 |
O25—C29 | 1.410 (9) | C43—H43B | 0.9900 |
O26—C30 | 1.407 (10) | C44—C45 | 1.520 (11) |
O26—C26 | 1.418 (8) | C44—H44A | 0.9900 |
C11—C12 | 1.352 (11) | C44—H44B | 0.9900 |
C11—C18 | 1.509 (12) | C45—C46 | 1.331 (11) |
C11—H11 | 0.9500 | C45—H45 | 0.9500 |
C12—C13 | 1.529 (12) | C46—C47 | 1.519 (12) |
C12—H12 | 0.9500 | C46—H46 | 0.9500 |
C13—C14 | 1.526 (12) | C47—C48 | 1.560 (11) |
C13—H13A | 0.9900 | C47—H47A | 0.9900 |
C13—H13B | 0.9900 | C47—H47B | 0.9900 |
C14—C15 | 1.468 (11) | C48—H48A | 0.9900 |
C14—H14A | 0.9900 | C48—H48B | 0.9900 |
C14—H14B | 0.9900 | C31—C32 | 1.521 (10) |
C15—C16 | 1.395 (10) | C31—C36 | 1.526 (9) |
C15—H15 | 0.9500 | C31—H31 | 1.0000 |
C16—C17 | 1.518 (11) | C32—C33 | 1.523 (10) |
C16—H16 | 0.9500 | C32—H32 | 1.0000 |
C17—C18 | 1.512 (12) | C33—C34 | 1.523 (10) |
C17—H17A | 0.9900 | C33—H33 | 1.0000 |
C17—H17B | 0.9900 | C37—H37A | 0.9800 |
C18—H18A | 0.9900 | C37—H37B | 0.9800 |
C18—H18B | 0.9900 | C37—H37C | 0.9800 |
C21—C26 | 1.495 (9) | C34—C35 | 1.541 (10) |
C21—C22 | 1.521 (9) | C34—H34 | 1.0000 |
C21—H21 | 1.0000 | C38—H38A | 0.9800 |
C22—C23 | 1.525 (10) | C38—H38B | 0.9800 |
C22—H22 | 1.0000 | C38—H38C | 0.9800 |
C23—C24 | 1.527 (10) | C35—C36 | 1.507 (10) |
C23—H23 | 1.0000 | C35—H35 | 1.0000 |
C27—H27A | 0.9800 | C39—H39A | 0.9800 |
C27—H27B | 0.9800 | C39—H39B | 0.9800 |
C27—H27C | 0.9800 | C39—H39C | 0.9800 |
C24—C25 | 1.522 (10) | C36—H36 | 1.0000 |
C24—H24 | 1.0000 | C40—H40A | 0.9800 |
C28—H28A | 0.9800 | C40—H40B | 0.9800 |
C28—H28B | 0.9800 | C40—H40C | 0.9800 |
C28—H28C | 0.9800 | C311—C312 | 1.386 (10) |
C25—C26 | 1.552 (11) | C311—C316 | 1.402 (11) |
C25—H25 | 1.0000 | C312—C313 | 1.401 (12) |
C29—H29A | 0.9800 | C312—H312 | 0.9500 |
C29—H29B | 0.9800 | C313—C314 | 1.376 (13) |
C29—H29C | 0.9800 | C313—H313 | 0.9500 |
C26—H26 | 1.0000 | C314—C315 | 1.379 (13) |
C30—H30A | 0.9800 | C314—H314 | 0.9500 |
C30—H30B | 0.9800 | C315—C316 | 1.383 (12) |
C30—H30C | 0.9800 | C315—H315 | 0.9500 |
C111—C112 | 1.391 (10) | C316—H316 | 0.9500 |
C111—C116 | 1.408 (11) | C321—C322 | 1.401 (11) |
C112—C113 | 1.390 (12) | C321—C326 | 1.411 (10) |
C112—H112 | 0.9500 | C322—C323 | 1.387 (11) |
C113—C114 | 1.386 (13) | C322—H322 | 0.9500 |
C113—H113 | 0.9500 | C323—C324 | 1.391 (12) |
C114—C115 | 1.398 (12) | C323—H323 | 0.9500 |
C114—H114 | 0.9500 | C324—C325 | 1.385 (12) |
C115—C116 | 1.384 (12) | C324—H324 | 0.9500 |
C115—H115 | 0.9500 | C325—C326 | 1.382 (12) |
C116—H116 | 0.9500 | C325—H325 | 0.9500 |
C121—C122 | 1.393 (12) | C326—H326 | 0.9500 |
C121—C126 | 1.418 (10) | C411—C416 | 1.382 (10) |
C122—C123 | 1.415 (12) | C411—C412 | 1.405 (11) |
C122—H122 | 0.9500 | C412—C413 | 1.391 (11) |
C123—C124 | 1.374 (13) | C412—H412 | 0.9500 |
C123—H123 | 0.9500 | C413—C414 | 1.384 (11) |
C124—C125 | 1.377 (14) | C413—H413 | 0.9500 |
C124—H124 | 0.9500 | C414—C415 | 1.390 (11) |
C125—C126 | 1.388 (12) | C414—H414 | 0.9500 |
C125—H125 | 0.9500 | C415—C416 | 1.373 (11) |
C126—H126 | 0.9500 | C415—H415 | 0.9500 |
C211—C212 | 1.415 (10) | C416—H416 | 0.9500 |
C211—C216 | 1.417 (11) | C421—C422 | 1.379 (11) |
C212—C213 | 1.406 (11) | C421—C426 | 1.411 (12) |
C212—H212 | 0.9500 | C422—C423 | 1.396 (12) |
C213—C214 | 1.378 (12) | C422—H422 | 0.9500 |
C213—H213 | 0.9500 | C423—C424 | 1.385 (14) |
C214—C215 | 1.437 (13) | C423—H423 | 0.9500 |
C214—H214 | 0.9500 | C424—C425 | 1.364 (13) |
C215—C216 | 1.343 (13) | C424—H424 | 0.9500 |
C215—H215 | 0.9500 | C425—C426 | 1.394 (12) |
C216—H216 | 0.9500 | C425—H425 | 0.9500 |
C221—C226 | 1.397 (11) | C426—H426 | 0.9500 |
C221—C222 | 1.409 (11) | C7—Cl7B | 1.726 (17) |
C222—C223 | 1.402 (11) | C7—Cl7A | 1.875 (18) |
C222—H222 | 0.9500 | C7—H7A | 1.034 |
C223—C224 | 1.366 (13) | C7—H7B | 1.037 |
C223—H223 | 0.9500 | C8—Cl8A | 1.752 (14) |
C224—C225 | 1.391 (12) | C8—Cl8B | 1.847 (13) |
C224—H224 | 0.9500 | C8—H8A | 1.029 |
C225—C226 | 1.387 (12) | C8—H8B | 1.031 |
C12—Rh1—C11 | 35.1 (3) | P4—Rh2—C45 | 169.7 (2) |
C12—Rh1—P2 | 96.7 (2) | P3—Rh2—C45 | 90.1 (2) |
C11—Rh1—P2 | 88.1 (2) | C41—Rh2—C45 | 93.2 (3) |
C12—Rh1—C15 | 80.1 (3) | C42—Rh2—C46 | 84.8 (3) |
C11—Rh1—C15 | 93.5 (3) | P4—Rh2—C46 | 156.0 (2) |
P2—Rh1—C15 | 171.6 (2) | P3—Rh2—C46 | 95.3 (2) |
C12—Rh1—P1 | 161.4 (2) | C41—Rh2—C46 | 78.1 (3) |
C11—Rh1—P1 | 162.9 (2) | C45—Rh2—C46 | 33.9 (3) |
P2—Rh1—P1 | 90.93 (7) | O3—P3—C321 | 97.5 (3) |
C15—Rh1—P1 | 89.9 (2) | O3—P3—C311 | 106.5 (3) |
C12—Rh1—C16 | 86.4 (3) | C321—P3—C311 | 105.7 (4) |
C11—Rh1—C16 | 78.7 (3) | O3—P3—Rh2 | 120.00 (19) |
P2—Rh1—C16 | 152.4 (2) | C321—P3—Rh2 | 110.1 (2) |
C15—Rh1—C16 | 35.7 (3) | C311—P3—Rh2 | 115.0 (2) |
P1—Rh1—C16 | 94.7 (2) | O4—P4—C421 | 102.3 (3) |
O1—P1—C121 | 99.6 (3) | O4—P4—C411 | 97.8 (3) |
O1—P1—C111 | 106.0 (3) | C421—P4—C411 | 104.8 (3) |
C121—P1—C111 | 105.3 (4) | O4—P4—Rh2 | 121.2 (2) |
O1—P1—Rh1 | 119.12 (19) | C421—P4—Rh2 | 111.4 (3) |
C121—P1—Rh1 | 111.1 (2) | C411—P4—Rh2 | 117.0 (2) |
C111—P1—Rh1 | 114.0 (2) | C31—O3—P3 | 125.3 (4) |
O2—P2—C211 | 96.4 (3) | C32—O4—P4 | 126.9 (5) |
O2—P2—C221 | 104.0 (3) | C33—O33—C37 | 114.5 (7) |
C211—P2—C221 | 104.3 (4) | C34—O34—C38 | 115.7 (7) |
O2—P2—Rh1 | 121.5 (2) | C35—O35—C39 | 115.0 (6) |
C211—P2—Rh1 | 118.1 (2) | C36—O36—C40 | 113.4 (6) |
C221—P2—Rh1 | 110.2 (3) | C42—C41—C48 | 126.6 (8) |
F11—B1—F14 | 108.8 (9) | C42—C41—Rh2 | 71.7 (5) |
F11—B1—F13 | 112.1 (9) | C48—C41—Rh2 | 108.2 (5) |
F14—B1—F13 | 112.2 (9) | C42—C41—H41 | 116.7 |
F11—B1—F12 | 110.8 (11) | C48—C41—H41 | 116.7 |
F14—B1—F12 | 105.4 (9) | Rh2—C41—H41 | 90.0 |
F13—B1—F12 | 107.4 (9) | C41—C42—C43 | 125.8 (8) |
F22—B2—F24 | 107.1 (11) | C41—C42—Rh2 | 73.5 (5) |
F22—B2—F23 | 109.1 (10) | C43—C42—Rh2 | 110.0 (5) |
F24—B2—F23 | 109.7 (9) | C41—C42—H42 | 117.1 |
F22—B2—F21 | 109.7 (8) | C43—C42—H42 | 117.1 |
F24—B2—F21 | 112.3 (10) | Rh2—C42—H42 | 86.3 |
F23—B2—F21 | 108.9 (9) | C44—C43—C42 | 115.7 (7) |
C21—O1—P1 | 127.1 (4) | C44—C43—H43A | 108.3 |
C22—O2—P2 | 125.8 (5) | C42—C43—H43A | 108.3 |
C23—O23—C27 | 113.8 (7) | C44—C43—H43B | 108.3 |
C28—O24—C24 | 115.7 (7) | C42—C43—H43B | 108.3 |
C25—O25—C29 | 114.2 (6) | H43A—C43—H43B | 107.4 |
C30—O26—C26 | 114.3 (6) | C43—C44—C45 | 114.0 (7) |
C12—C11—C18 | 127.2 (9) | C43—C44—H44A | 108.8 |
C12—C11—Rh1 | 71.3 (5) | C45—C44—H44A | 108.8 |
C18—C11—Rh1 | 107.8 (5) | C43—C44—H44B | 108.8 |
C12—C11—H11 | 116.4 | C45—C44—H44B | 108.8 |
C18—C11—H11 | 116.4 | H44A—C44—H44B | 107.7 |
Rh1—C11—H11 | 90.9 | C46—C45—C44 | 126.5 (8) |
C11—C12—C13 | 123.7 (8) | C46—C45—Rh2 | 73.9 (6) |
C11—C12—Rh1 | 73.6 (5) | C44—C45—Rh2 | 105.4 (5) |
C13—C12—Rh1 | 110.5 (6) | C46—C45—H45 | 116.7 |
C11—C12—H12 | 118.2 | C44—C45—H45 | 116.7 |
C13—C12—H12 | 118.2 | Rh2—C45—H45 | 90.8 |
Rh1—C12—H12 | 85.9 | C45—C46—C47 | 124.8 (8) |
C14—C13—C12 | 114.0 (7) | C45—C46—Rh2 | 72.2 (6) |
C14—C13—H13A | 108.7 | C47—C46—Rh2 | 113.5 (6) |
C12—C13—H13A | 108.7 | C45—C46—H46 | 117.6 |
C14—C13—H13B | 108.7 | C47—C46—H46 | 117.6 |
C12—C13—H13B | 108.7 | Rh2—C46—H46 | 84.2 |
H13A—C13—H13B | 107.6 | C46—C47—C48 | 110.9 (7) |
C15—C14—C13 | 114.7 (8) | C46—C47—H47A | 109.5 |
C15—C14—H14A | 108.6 | C48—C47—H47A | 109.5 |
C13—C14—H14A | 108.6 | C46—C47—H47B | 109.5 |
C15—C14—H14B | 108.6 | C48—C47—H47B | 109.5 |
C13—C14—H14B | 108.6 | H47A—C47—H47B | 108.0 |
H14A—C14—H14B | 107.6 | C41—C48—C47 | 115.0 (7) |
C16—C15—C14 | 127.3 (8) | C41—C48—H48A | 108.5 |
C16—C15—Rh1 | 73.4 (5) | C47—C48—H48A | 108.5 |
C14—C15—Rh1 | 106.5 (6) | C41—C48—H48B | 108.5 |
C16—C15—H15 | 116.4 | C47—C48—H48B | 108.5 |
C14—C15—H15 | 116.4 | H48A—C48—H48B | 107.5 |
Rh1—C15—H15 | 90.1 | O3—C31—C32 | 113.8 (6) |
C15—C16—C17 | 122.4 (8) | O3—C31—C36 | 111.9 (6) |
C15—C16—Rh1 | 70.9 (5) | C32—C31—C36 | 111.9 (6) |
C17—C16—Rh1 | 111.7 (6) | O3—C31—H31 | 106.2 |
C15—C16—H16 | 118.8 | C32—C31—H31 | 106.2 |
C17—C16—H16 | 118.8 | C36—C31—H31 | 106.2 |
Rh1—C16—H16 | 87.5 | O4—C32—C31 | 109.7 (5) |
C18—C17—C16 | 112.9 (7) | O4—C32—C33 | 106.5 (6) |
C18—C17—H17A | 109.0 | C31—C32—C33 | 113.1 (6) |
C16—C17—H17A | 109.0 | O4—C32—H32 | 109.2 |
C18—C17—H17B | 109.0 | C31—C32—H32 | 109.2 |
C16—C17—H17B | 109.0 | C33—C32—H32 | 109.2 |
H17A—C17—H17B | 107.8 | O33—C33—C32 | 104.9 (6) |
C11—C18—C17 | 114.8 (7) | O33—C33—C34 | 112.5 (6) |
C11—C18—H18A | 108.6 | C32—C33—C34 | 112.2 (6) |
C17—C18—H18A | 108.6 | O33—C33—H33 | 109.0 |
C11—C18—H18B | 108.6 | C32—C33—H33 | 109.0 |
C17—C18—H18B | 108.6 | C34—C33—H33 | 109.0 |
H18A—C18—H18B | 107.5 | O33—C37—H37A | 109.5 |
O1—C21—C26 | 109.8 (6) | O33—C37—H37B | 109.5 |
O1—C21—C22 | 111.4 (5) | H37A—C37—H37B | 109.5 |
C26—C21—C22 | 114.6 (6) | O33—C37—H37C | 109.5 |
O1—C21—H21 | 106.9 | H37A—C37—H37C | 109.5 |
C26—C21—H21 | 106.9 | H37B—C37—H37C | 109.5 |
C22—C21—H21 | 106.9 | O34—C34—C33 | 107.9 (6) |
O2—C22—C21 | 111.4 (5) | O34—C34—C35 | 110.7 (6) |
O2—C22—C23 | 105.2 (6) | C33—C34—C35 | 108.3 (6) |
C21—C22—C23 | 113.3 (6) | O34—C34—H34 | 110.0 |
O2—C22—H22 | 108.9 | C33—C34—H34 | 110.0 |
C21—C22—H22 | 108.9 | C35—C34—H34 | 110.0 |
C23—C22—H22 | 108.9 | O34—C38—H38A | 109.5 |
O23—C23—C22 | 106.2 (6) | O34—C38—H38B | 109.5 |
O23—C23—C24 | 113.4 (6) | H38A—C38—H38B | 109.5 |
C22—C23—C24 | 111.0 (6) | O34—C38—H38C | 109.5 |
O23—C23—H23 | 108.7 | H38A—C38—H38C | 109.5 |
C22—C23—H23 | 108.7 | H38B—C38—H38C | 109.5 |
C24—C23—H23 | 108.7 | O35—C35—C36 | 111.3 (6) |
O23—C27—H27A | 109.5 | O35—C35—C34 | 108.0 (6) |
O23—C27—H27B | 109.5 | C36—C35—C34 | 109.5 (6) |
H27A—C27—H27B | 109.5 | O35—C35—H35 | 109.3 |
O23—C27—H27C | 109.5 | C36—C35—H35 | 109.3 |
H27A—C27—H27C | 109.5 | C34—C35—H35 | 109.3 |
H27B—C27—H27C | 109.5 | O35—C39—H39A | 109.5 |
O24—C24—C25 | 105.0 (6) | O35—C39—H39B | 109.5 |
O24—C24—C23 | 112.6 (6) | H39A—C39—H39B | 109.5 |
C25—C24—C23 | 110.7 (6) | O35—C39—H39C | 109.5 |
O24—C24—H24 | 109.4 | H39A—C39—H39C | 109.5 |
C25—C24—H24 | 109.4 | H39B—C39—H39C | 109.5 |
C23—C24—H24 | 109.4 | O36—C36—C35 | 113.9 (6) |
O24—C28—H28A | 109.5 | O36—C36—C31 | 106.7 (5) |
O24—C28—H28B | 109.5 | C35—C36—C31 | 110.9 (6) |
H28A—C28—H28B | 109.5 | O36—C36—H36 | 108.4 |
O24—C28—H28C | 109.5 | C35—C36—H36 | 108.4 |
H28A—C28—H28C | 109.5 | C31—C36—H36 | 108.4 |
H28B—C28—H28C | 109.5 | O36—C40—H40A | 109.5 |
O25—C25—C24 | 108.7 (6) | O36—C40—H40B | 109.5 |
O25—C25—C26 | 111.6 (6) | H40A—C40—H40B | 109.5 |
C24—C25—C26 | 108.3 (6) | O36—C40—H40C | 109.5 |
O25—C25—H25 | 109.4 | H40A—C40—H40C | 109.5 |
C24—C25—H25 | 109.4 | H40B—C40—H40C | 109.5 |
C26—C25—H25 | 109.4 | C312—C311—C316 | 120.3 (7) |
O25—C29—H29A | 109.5 | C312—C311—P3 | 118.4 (6) |
O25—C29—H29B | 109.5 | C316—C311—P3 | 121.1 (6) |
H29A—C29—H29B | 109.5 | C311—C312—C313 | 119.9 (8) |
O25—C29—H29C | 109.5 | C311—C312—H312 | 120.0 |
H29A—C29—H29C | 109.5 | C313—C312—H312 | 120.0 |
H29B—C29—H29C | 109.5 | C314—C313—C312 | 118.7 (9) |
O26—C26—C21 | 107.1 (5) | C314—C313—H313 | 120.7 |
O26—C26—C25 | 112.8 (6) | C312—C313—H313 | 120.7 |
C21—C26—C25 | 109.7 (6) | C313—C314—C315 | 122.0 (9) |
O26—C26—H26 | 109.1 | C313—C314—H314 | 119.0 |
C21—C26—H26 | 109.1 | C315—C314—H314 | 119.0 |
C25—C26—H26 | 109.1 | C314—C315—C316 | 119.6 (9) |
O26—C30—H30A | 109.5 | C314—C315—H315 | 120.2 |
O26—C30—H30B | 109.5 | C316—C315—H315 | 120.2 |
H30A—C30—H30B | 109.5 | C315—C316—C311 | 119.4 (8) |
O26—C30—H30C | 109.5 | C315—C316—H316 | 120.3 |
H30A—C30—H30C | 109.5 | C311—C316—H316 | 120.3 |
H30B—C30—H30C | 109.5 | C322—C321—C326 | 118.6 (7) |
C112—C111—C116 | 120.0 (7) | C322—C321—P3 | 121.5 (6) |
C112—C111—P1 | 119.2 (6) | C326—C321—P3 | 119.5 (6) |
C116—C111—P1 | 120.8 (6) | C323—C322—C321 | 121.4 (8) |
C113—C112—C111 | 120.6 (8) | C323—C322—H322 | 119.3 |
C113—C112—H112 | 119.7 | C321—C322—H322 | 119.3 |
C111—C112—H112 | 119.7 | C322—C323—C324 | 118.7 (9) |
C114—C113—C112 | 118.9 (9) | C322—C323—H323 | 120.6 |
C114—C113—H113 | 120.5 | C324—C323—H323 | 120.6 |
C112—C113—H113 | 120.5 | C325—C324—C323 | 121.0 (9) |
C113—C114—C115 | 121.3 (9) | C325—C324—H324 | 119.5 |
C113—C114—H114 | 119.4 | C323—C324—H324 | 119.5 |
C115—C114—H114 | 119.4 | C326—C325—C324 | 120.4 (9) |
C116—C115—C114 | 119.7 (8) | C326—C325—H325 | 119.8 |
C116—C115—H115 | 120.2 | C324—C325—H325 | 119.8 |
C114—C115—H115 | 120.2 | C325—C326—C321 | 119.9 (8) |
C115—C116—C111 | 119.5 (8) | C325—C326—H326 | 120.1 |
C115—C116—H116 | 120.3 | C321—C326—H326 | 120.1 |
C111—C116—H116 | 120.3 | C416—C411—C412 | 119.5 (6) |
C122—C121—C126 | 120.0 (7) | C416—C411—P4 | 122.9 (6) |
C122—C121—P1 | 120.9 (6) | C412—C411—P4 | 117.6 (5) |
C126—C121—P1 | 118.5 (6) | C413—C412—C411 | 118.9 (7) |
C121—C122—C123 | 119.9 (8) | C413—C412—H412 | 120.5 |
C121—C122—H122 | 120.0 | C411—C412—H412 | 120.5 |
C123—C122—H122 | 120.0 | C414—C413—C412 | 120.8 (8) |
C124—C123—C122 | 119.8 (10) | C414—C413—H413 | 119.6 |
C124—C123—H123 | 120.1 | C412—C413—H413 | 119.6 |
C122—C123—H123 | 120.1 | C413—C414—C415 | 119.8 (8) |
C123—C124—C125 | 120.0 (10) | C413—C414—H414 | 120.1 |
C123—C124—H124 | 120.0 | C415—C414—H414 | 120.1 |
C125—C124—H124 | 120.0 | C416—C415—C414 | 119.7 (8) |
C124—C125—C126 | 122.4 (9) | C416—C415—H415 | 120.1 |
C124—C125—H125 | 118.8 | C414—C415—H415 | 120.1 |
C126—C125—H125 | 118.8 | C415—C416—C411 | 121.2 (7) |
C125—C126—C121 | 117.9 (8) | C415—C416—H416 | 119.4 |
C125—C126—H126 | 121.1 | C411—C416—H416 | 119.4 |
C121—C126—H126 | 121.1 | C422—C421—C426 | 119.6 (7) |
C212—C211—C216 | 116.7 (7) | C422—C421—P4 | 120.8 (6) |
C212—C211—P2 | 123.7 (6) | C426—C421—P4 | 119.6 (6) |
C216—C211—P2 | 119.4 (6) | C421—C422—C423 | 119.5 (9) |
C213—C212—C211 | 122.5 (7) | C421—C422—H422 | 120.2 |
C213—C212—H212 | 118.8 | C423—C422—H422 | 120.2 |
C211—C212—H212 | 118.8 | C424—C423—C422 | 121.1 (9) |
C214—C213—C212 | 118.9 (8) | C424—C423—H423 | 119.5 |
C214—C213—H213 | 120.5 | C422—C423—H423 | 119.5 |
C212—C213—H213 | 120.5 | C425—C424—C423 | 119.3 (9) |
C213—C214—C215 | 118.9 (9) | C425—C424—H424 | 120.3 |
C213—C214—H214 | 120.6 | C423—C424—H424 | 120.3 |
C215—C214—H214 | 120.6 | C424—C425—C426 | 121.2 (9) |
C216—C215—C214 | 121.7 (9) | C424—C425—H425 | 119.4 |
C216—C215—H215 | 119.1 | C426—C425—H425 | 119.4 |
C214—C215—H215 | 119.1 | C425—C426—C421 | 119.3 (8) |
C215—C216—C211 | 121.2 (8) | C425—C426—H426 | 120.4 |
C215—C216—H216 | 119.4 | C421—C426—H426 | 120.4 |
C211—C216—H216 | 119.4 | Cl71—C7—Cl72 | 112.5 (10) |
C226—C221—C222 | 119.7 (7) | Cl71—C7—Cl7B | 113.7 (10) |
C226—C221—P2 | 120.2 (6) | Cl72—C7—Cl7B | 96.5 (9) |
C222—C221—P2 | 120.1 (6) | Cl71—C7—Cl7A | 104.8 (9) |
C223—C222—C221 | 119.4 (8) | Cl72—C7—Cl7A | 120.4 (8) |
C223—C222—H222 | 120.3 | Cl71—C7—H7A | 106.4 (10) |
C221—C222—H222 | 120.3 | Cl72—C7—H7A | 106.7 (13) |
C224—C223—C222 | 120.1 (8) | Cl7B—C7—H7A | 120.6 (13) |
C224—C223—H223 | 119.9 | Cl7A—C7—H7A | 105.1 (12) |
C222—C223—H223 | 119.9 | Cl71—C7—H7B | 111.1 (10) |
C223—C224—C225 | 120.7 (8) | Cl72—C7—H7B | 111.6 (13) |
C223—C224—H224 | 119.7 | Cl7B—C7—H7B | 110.7 (12) |
C225—C224—H224 | 119.7 | Cl7A—C7—H7B | 95.1 (12) |
C226—C225—C224 | 120.4 (8) | Cl81—C8—Cl8A | 108.2 (8) |
C226—C225—H225 | 119.8 | Cl81—C8—Cl82 | 110.5 (8) |
C224—C225—H225 | 119.8 | Cl8A—C8—Cl82 | 124.7 (8) |
C225—C226—C221 | 119.6 (8) | Cl81—C8—Cl8B | 111.4 (7) |
C225—C226—H226 | 120.2 | Cl82—C8—Cl8B | 90.2 (8) |
C221—C226—H226 | 120.2 | Cl81—C8—H8A | 103.5 (9) |
C42—Rh2—P4 | 96.3 (2) | Cl8A—C8—H8A | 103.0 (10) |
C42—Rh2—P3 | 162.3 (2) | Cl82—C8—H8A | 104.6 (10) |
P4—Rh2—P3 | 90.69 (7) | Cl8B—C8—H8A | 134.2 (10) |
C42—Rh2—C41 | 34.7 (3) | Cl81—C8—H8B | 113.5 (11) |
P4—Rh2—C41 | 89.2 (2) | Cl8A—C8—H8B | 82.6 (8) |
P3—Rh2—C41 | 162.2 (2) | Cl82—C8—H8B | 114.7 (11) |
C42—Rh2—C45 | 80.1 (3) | Cl8B—C8—H8B | 114.3 (9) |
C12—Rh1—P1—O1 | 124.6 (8) | C45—Rh2—P3—O3 | 178.5 (3) |
C11—Rh1—P1—O1 | −76.6 (8) | C46—Rh2—P3—O3 | −148.0 (3) |
P2—Rh1—P1—O1 | 10.1 (2) | C42—Rh2—P3—C321 | −125.9 (8) |
C15—Rh1—P1—O1 | −178.3 (3) | P4—Rh2—P3—C321 | 120.5 (3) |
C16—Rh1—P1—O1 | −142.9 (3) | C41—Rh2—P3—C321 | 31.0 (8) |
C12—Rh1—P1—C121 | −120.6 (8) | C45—Rh2—P3—C321 | −69.8 (3) |
C11—Rh1—P1—C121 | 38.2 (9) | C46—Rh2—P3—C321 | −36.2 (4) |
P2—Rh1—P1—C121 | 124.9 (3) | C42—Rh2—P3—C311 | −6.7 (8) |
C15—Rh1—P1—C121 | −63.5 (3) | P4—Rh2—P3—C311 | −120.3 (3) |
C16—Rh1—P1—C121 | −28.1 (3) | C41—Rh2—P3—C311 | 150.2 (8) |
C12—Rh1—P1—C111 | −1.8 (8) | C45—Rh2—P3—C311 | 49.4 (4) |
C11—Rh1—P1—C111 | 157.0 (8) | C46—Rh2—P3—C311 | 83.0 (4) |
P2—Rh1—P1—C111 | −116.3 (3) | C42—Rh2—P4—O4 | −121.1 (3) |
C15—Rh1—P1—C111 | 55.3 (4) | P3—Rh2—P4—O4 | 42.7 (2) |
C16—Rh1—P1—C111 | 90.7 (4) | C41—Rh2—P4—O4 | −155.1 (3) |
C12—Rh1—P2—O2 | −118.9 (3) | C45—Rh2—P4—O4 | −51.7 (12) |
C11—Rh1—P2—O2 | −152.9 (3) | C46—Rh2—P4—O4 | 147.4 (6) |
P1—Rh1—P2—O2 | 44.1 (2) | C42—Rh2—P4—C421 | 118.6 (3) |
C16—Rh1—P2—O2 | 146.1 (5) | P3—Rh2—P4—C421 | −77.7 (3) |
C12—Rh1—P2—C211 | −0.5 (4) | C41—Rh2—P4—C421 | 84.6 (3) |
C11—Rh1—P2—C211 | −34.5 (3) | C45—Rh2—P4—C421 | −172.1 (11) |
P1—Rh1—P2—C211 | 162.5 (3) | C46—Rh2—P4—C421 | 27.0 (6) |
C16—Rh1—P2—C211 | −95.5 (5) | C42—Rh2—P4—C411 | −2.0 (3) |
C12—Rh1—P2—C221 | 119.2 (3) | P3—Rh2—P4—C411 | 161.8 (3) |
C11—Rh1—P2—C221 | 85.1 (3) | C41—Rh2—P4—C411 | −36.0 (3) |
P1—Rh1—P2—C221 | −77.8 (3) | C45—Rh2—P4—C411 | 67.4 (12) |
C16—Rh1—P2—C221 | 24.2 (5) | C46—Rh2—P4—C411 | −93.5 (6) |
C121—P1—O1—C21 | 161.1 (5) | C321—P3—O3—C31 | 164.0 (5) |
C111—P1—O1—C21 | 52.0 (6) | C311—P3—O3—C31 | 55.1 (6) |
Rh1—P1—O1—C21 | −78.0 (5) | Rh2—P3—O3—C31 | −77.7 (5) |
C211—P2—O2—C22 | −143.3 (5) | C421—P4—O4—C32 | 115.7 (6) |
C221—P2—O2—C22 | 110.2 (6) | C411—P4—O4—C32 | −137.2 (6) |
Rh1—P2—O2—C22 | −14.7 (6) | Rh2—P4—O4—C32 | −9.0 (6) |
P2—Rh1—C11—C12 | 104.5 (6) | P4—Rh2—C41—C42 | 102.4 (6) |
C15—Rh1—C11—C12 | −67.3 (6) | P3—Rh2—C41—C42 | −167.9 (5) |
P1—Rh1—C11—C12 | −168.4 (6) | C45—Rh2—C41—C42 | −67.6 (6) |
C16—Rh1—C11—C12 | −99.9 (6) | C46—Rh2—C41—C42 | −98.2 (6) |
C12—Rh1—C11—C18 | 124.2 (9) | C42—Rh2—C41—C48 | 123.5 (9) |
P2—Rh1—C11—C18 | −131.3 (6) | P4—Rh2—C41—C48 | −134.1 (5) |
C15—Rh1—C11—C18 | 56.9 (6) | P3—Rh2—C41—C48 | −44.4 (11) |
P1—Rh1—C11—C18 | −44.2 (12) | C45—Rh2—C41—C48 | 55.9 (6) |
C16—Rh1—C11—C18 | 24.3 (6) | C46—Rh2—C41—C48 | 25.4 (6) |
C18—C11—C12—C13 | 5.5 (14) | C48—C41—C42—C43 | 3.5 (14) |
Rh1—C11—C12—C13 | 104.0 (8) | Rh2—C41—C42—C43 | 103.0 (8) |
C18—C11—C12—Rh1 | −98.6 (8) | C48—C41—C42—Rh2 | −99.5 (8) |
P2—Rh1—C12—C11 | −77.0 (6) | P4—Rh2—C42—C41 | −79.3 (6) |
C15—Rh1—C12—C11 | 110.9 (6) | P3—Rh2—C42—C41 | 167.8 (5) |
P1—Rh1—C12—C11 | 169.4 (6) | C45—Rh2—C42—C41 | 110.5 (6) |
C16—Rh1—C12—C11 | 75.5 (6) | C46—Rh2—C42—C41 | 76.6 (6) |
C11—Rh1—C12—C13 | −120.4 (9) | P4—Rh2—C42—C43 | 157.9 (5) |
P2—Rh1—C12—C13 | 162.5 (5) | P3—Rh2—C42—C43 | 45.0 (11) |
C15—Rh1—C12—C13 | −9.6 (6) | C41—Rh2—C42—C43 | −122.8 (9) |
P1—Rh1—C12—C13 | 48.9 (11) | C45—Rh2—C42—C43 | −12.3 (5) |
C16—Rh1—C12—C13 | −45.0 (6) | C46—Rh2—C42—C43 | −46.2 (6) |
C11—C12—C13—C14 | −93.1 (10) | C41—C42—C43—C44 | −91.0 (11) |
Rh1—C12—C13—C14 | −9.6 (9) | Rh2—C42—C43—C44 | −7.3 (9) |
C12—C13—C14—C15 | 35.8 (11) | C42—C43—C44—C45 | 34.7 (11) |
C13—C14—C15—C16 | 39.8 (14) | C43—C44—C45—C46 | 38.8 (13) |
C13—C14—C15—Rh1 | −41.7 (9) | C43—C44—C45—Rh2 | −42.3 (9) |
C12—Rh1—C15—C16 | −97.6 (5) | C42—Rh2—C45—C46 | −95.5 (6) |
C11—Rh1—C15—C16 | −65.0 (5) | P4—Rh2—C45—C46 | −166.2 (9) |
P1—Rh1—C15—C16 | 98.2 (5) | P3—Rh2—C45—C46 | 99.4 (5) |
C12—Rh1—C15—C14 | 27.2 (6) | C41—Rh2—C45—C46 | −63.2 (6) |
C11—Rh1—C15—C14 | 59.8 (6) | C42—Rh2—C45—C44 | 28.8 (5) |
P1—Rh1—C15—C14 | −137.0 (5) | P4—Rh2—C45—C44 | −41.9 (14) |
C16—Rh1—C15—C14 | 124.8 (8) | P3—Rh2—C45—C44 | −136.4 (5) |
C14—C15—C16—C17 | 5.7 (15) | C41—Rh2—C45—C44 | 61.1 (5) |
Rh1—C15—C16—C17 | 104.1 (8) | C46—Rh2—C45—C44 | 124.2 (8) |
C14—C15—C16—Rh1 | −98.4 (10) | C44—C45—C46—C47 | 9.3 (16) |
C12—Rh1—C16—C15 | 78.1 (5) | Rh2—C45—C46—C47 | 106.7 (9) |
C11—Rh1—C16—C15 | 112.7 (5) | C44—C45—C46—Rh2 | −97.4 (9) |
P2—Rh1—C16—C15 | 175.6 (4) | C42—Rh2—C46—C45 | 80.0 (5) |
P1—Rh1—C16—C15 | −83.2 (5) | P4—Rh2—C46—C45 | 174.0 (4) |
C12—Rh1—C16—C17 | −40.1 (6) | P3—Rh2—C46—C45 | −82.3 (5) |
C11—Rh1—C16—C17 | −5.6 (6) | C41—Rh2—C46—C45 | 114.4 (6) |
P2—Rh1—C16—C17 | 57.4 (8) | C42—Rh2—C46—C47 | −41.0 (6) |
C15—Rh1—C16—C17 | −118.2 (8) | P4—Rh2—C46—C47 | 53.0 (10) |
P1—Rh1—C16—C17 | 158.5 (5) | P3—Rh2—C46—C47 | 156.8 (6) |
C15—C16—C17—C18 | −95.3 (10) | C41—Rh2—C46—C47 | −6.5 (6) |
Rh1—C16—C17—C18 | −14.7 (9) | C45—Rh2—C46—C47 | −120.9 (9) |
C12—C11—C18—C17 | 38.1 (12) | C45—C46—C47—C48 | −97.2 (11) |
Rh1—C11—C18—C17 | −41.7 (8) | Rh2—C46—C47—C48 | −13.1 (9) |
C16—C17—C18—C11 | 38.4 (10) | C42—C41—C48—C47 | 38.2 (12) |
P1—O1—C21—C26 | −92.8 (6) | Rh2—C41—C48—C47 | −42.2 (8) |
P1—O1—C21—C22 | 35.2 (8) | C46—C47—C48—C41 | 37.5 (10) |
P2—O2—C22—C21 | −77.8 (7) | P3—O3—C31—C32 | 37.8 (8) |
P2—O2—C22—C23 | 159.0 (5) | P3—O3—C31—C36 | −90.4 (6) |
O1—C21—C22—O2 | 68.5 (8) | P4—O4—C32—C31 | −80.3 (7) |
C26—C21—C22—O2 | −166.0 (6) | P4—O4—C32—C33 | 157.1 (5) |
O1—C21—C22—C23 | −173.0 (6) | O3—C31—C32—O4 | 64.8 (8) |
C26—C21—C22—C23 | −47.5 (9) | C36—C31—C32—O4 | −167.1 (6) |
C27—O23—C23—C22 | 165.1 (7) | O3—C31—C32—C33 | −176.5 (6) |
C27—O23—C23—C24 | −72.7 (9) | C36—C31—C32—C33 | −48.4 (9) |
O2—C22—C23—O23 | −66.6 (7) | C37—O33—C33—C32 | −177.3 (7) |
C21—C22—C23—O23 | 171.4 (6) | C37—O33—C33—C34 | −55.0 (9) |
O2—C22—C23—C24 | 169.7 (6) | O4—C32—C33—O33 | −65.9 (7) |
C21—C22—C23—C24 | 47.7 (8) | C31—C32—C33—O33 | 173.5 (6) |
C28—O24—C24—C25 | −148.8 (8) | O4—C32—C33—C34 | 171.6 (6) |
C28—O24—C24—C23 | 90.6 (9) | C31—C32—C33—C34 | 51.1 (8) |
O23—C23—C24—O24 | −58.8 (9) | C38—O34—C34—C33 | 162.0 (8) |
C22—C23—C24—O24 | 60.6 (8) | C38—O34—C34—C35 | −79.7 (9) |
O23—C23—C24—C25 | −176.1 (7) | O33—C33—C34—O34 | −55.2 (8) |
C22—C23—C24—C25 | −56.6 (9) | C32—C33—C34—O34 | 62.8 (8) |
C29—O25—C25—C24 | −148.0 (7) | O33—C33—C34—C35 | −175.0 (6) |
C29—O25—C25—C26 | 92.6 (8) | C32—C33—C34—C35 | −57.0 (8) |
O24—C24—C25—O25 | 179.4 (6) | C39—O35—C35—C36 | 92.6 (8) |
C23—C24—C25—O25 | −58.7 (8) | C39—O35—C35—C34 | −147.1 (7) |
O24—C24—C25—C26 | −59.2 (7) | O34—C34—C35—O35 | −177.2 (6) |
C23—C24—C25—C26 | 62.7 (8) | C33—C34—C35—O35 | −59.1 (8) |
C30—O26—C26—C21 | 161.1 (7) | O34—C34—C35—C36 | −55.8 (8) |
C30—O26—C26—C25 | −78.1 (8) | C33—C34—C35—C36 | 62.2 (8) |
O1—C21—C26—O26 | −57.9 (7) | C40—O36—C36—C35 | −73.7 (8) |
C22—C21—C26—O26 | 175.8 (6) | C40—O36—C36—C31 | 163.6 (7) |
O1—C21—C26—C25 | 179.3 (5) | O35—C35—C36—O36 | −62.1 (8) |
C22—C21—C26—C25 | 53.1 (8) | C34—C35—C36—O36 | 178.5 (6) |
O25—C25—C26—O26 | −59.7 (8) | O35—C35—C36—C31 | 58.2 (8) |
C24—C25—C26—O26 | −179.3 (6) | C34—C35—C36—C31 | −61.2 (7) |
O25—C25—C26—C21 | 59.6 (7) | O3—C31—C36—O36 | −52.6 (8) |
C24—C25—C26—C21 | −60.0 (8) | C32—C31—C36—O36 | 178.3 (6) |
O1—P1—C111—C112 | −117.6 (7) | O3—C31—C36—C35 | −177.1 (6) |
C121—P1—C111—C112 | 137.5 (7) | C32—C31—C36—C35 | 53.8 (8) |
Rh1—P1—C111—C112 | 15.4 (8) | O3—P3—C311—C312 | −112.6 (7) |
O1—P1—C111—C116 | 60.6 (8) | C321—P3—C311—C312 | 144.4 (7) |
C121—P1—C111—C116 | −44.3 (8) | Rh2—P3—C311—C312 | 22.8 (8) |
Rh1—P1—C111—C116 | −166.4 (6) | O3—P3—C311—C316 | 62.8 (7) |
C116—C111—C112—C113 | −1.0 (13) | C321—P3—C311—C316 | −40.1 (8) |
P1—C111—C112—C113 | 177.2 (7) | Rh2—P3—C311—C316 | −161.7 (6) |
C111—C112—C113—C114 | −0.1 (14) | C316—C311—C312—C313 | 1.5 (13) |
C112—C113—C114—C115 | 1.4 (15) | P3—C311—C312—C313 | 177.0 (7) |
C113—C114—C115—C116 | −1.5 (15) | C311—C312—C313—C314 | 1.0 (14) |
C114—C115—C116—C111 | 0.4 (13) | C312—C313—C314—C315 | −2.6 (16) |
C112—C111—C116—C115 | 0.8 (13) | C313—C314—C315—C316 | 1.7 (16) |
P1—C111—C116—C115 | −177.3 (7) | C314—C315—C316—C311 | 0.8 (14) |
O1—P1—C121—C122 | −139.1 (6) | C312—C311—C316—C315 | −2.4 (13) |
C111—P1—C121—C122 | −29.4 (7) | P3—C311—C316—C315 | −177.8 (7) |
Rh1—P1—C121—C122 | 94.5 (6) | O3—P3—C321—C322 | −140.6 (6) |
O1—P1—C121—C126 | 49.6 (6) | C311—P3—C321—C322 | −31.1 (7) |
C111—P1—C121—C126 | 159.2 (6) | Rh2—P3—C321—C322 | 93.6 (6) |
Rh1—P1—C121—C126 | −76.8 (6) | O3—P3—C321—C326 | 47.0 (6) |
C126—C121—C122—C123 | 1.4 (11) | C311—P3—C321—C326 | 156.5 (6) |
P1—C121—C122—C123 | −169.8 (6) | Rh2—P3—C321—C326 | −78.8 (6) |
C121—C122—C123—C124 | −0.9 (13) | C326—C321—C322—C323 | 2.0 (11) |
C122—C123—C124—C125 | 0.4 (14) | P3—C321—C322—C323 | −170.5 (6) |
C123—C124—C125—C126 | −0.3 (14) | C321—C322—C323—C324 | −1.4 (12) |
C124—C125—C126—C121 | 0.8 (12) | C322—C323—C324—C325 | 0.9 (12) |
C122—C121—C126—C125 | −1.3 (11) | C323—C324—C325—C326 | −1.1 (12) |
P1—C121—C126—C125 | 170.1 (6) | C324—C325—C326—C321 | 1.7 (12) |
O2—P2—C211—C212 | −127.9 (6) | C322—C321—C326—C325 | −2.1 (11) |
C221—P2—C211—C212 | −21.6 (7) | P3—C321—C326—C325 | 170.5 (6) |
Rh1—P2—C211—C212 | 101.1 (6) | O4—P4—C411—C416 | −134.5 (6) |
O2—P2—C211—C216 | 56.7 (6) | C421—P4—C411—C416 | −29.6 (7) |
C221—P2—C211—C216 | 162.9 (6) | Rh2—P4—C411—C416 | 94.4 (6) |
Rh1—P2—C211—C216 | −74.4 (6) | O4—P4—C411—C412 | 46.4 (7) |
C216—C211—C212—C213 | −1.2 (12) | C421—P4—C411—C412 | 151.4 (6) |
P2—C211—C212—C213 | −176.7 (7) | Rh2—P4—C411—C412 | −84.6 (6) |
C211—C212—C213—C214 | 1.4 (14) | C416—C411—C412—C413 | −2.2 (12) |
C212—C213—C214—C215 | −1.2 (14) | P4—C411—C412—C413 | 176.8 (7) |
C213—C214—C215—C216 | 0.9 (16) | C411—C412—C413—C414 | −0.1 (13) |
C214—C215—C216—C211 | −0.7 (15) | C412—C413—C414—C415 | 1.5 (14) |
C212—C211—C216—C215 | 0.8 (12) | C413—C414—C415—C416 | −0.5 (14) |
P2—C211—C216—C215 | 176.5 (8) | C414—C415—C416—C411 | −1.8 (13) |
O2—P2—C221—C226 | 31.4 (7) | C412—C411—C416—C415 | 3.2 (12) |
C211—P2—C221—C226 | −69.1 (7) | P4—C411—C416—C415 | −175.8 (6) |
Rh1—P2—C221—C226 | 163.2 (5) | O4—P4—C421—C422 | −150.9 (6) |
O2—P2—C221—C222 | −147.4 (6) | C411—P4—C421—C422 | 107.5 (7) |
C211—P2—C221—C222 | 112.1 (7) | Rh2—P4—C421—C422 | −20.0 (7) |
Rh1—P2—C221—C222 | −15.6 (7) | O4—P4—C421—C426 | 29.4 (7) |
C226—C221—C222—C223 | 2.7 (12) | C411—P4—C421—C426 | −72.2 (7) |
P2—C221—C222—C223 | −178.6 (6) | Rh2—P4—C421—C426 | 160.3 (5) |
C221—C222—C223—C224 | −2.1 (13) | C426—C421—C422—C423 | 0.2 (12) |
C222—C223—C224—C225 | 1.4 (13) | P4—C421—C422—C423 | −179.5 (7) |
C223—C224—C225—C226 | −1.3 (12) | C421—C422—C423—C424 | 0.4 (13) |
C224—C225—C226—C221 | 1.9 (12) | C422—C423—C424—C425 | −0.8 (14) |
C222—C221—C226—C225 | −2.6 (11) | C423—C424—C425—C426 | 0.6 (13) |
P2—C221—C226—C225 | 178.7 (6) | C424—C425—C426—C421 | 0.0 (12) |
C42—Rh2—P3—O3 | 122.4 (8) | C422—C421—C426—C425 | −0.4 (11) |
P4—Rh2—P3—O3 | 8.7 (2) | P4—C421—C426—C425 | 179.3 (6) |
C41—Rh2—P3—O3 | −80.8 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···F23i | 1.03 | 2.39 | 3.402 (17) | 166 |
C8—H8A···F12ii | 1.03 | 2.29 | 3.148 (16) | 139 |
C8—H8A···F14ii | 1.03 | 2.34 | 3.262 (14) | 149 |
C113—H113···F23i | 0.95 | 2.45 | 3.258 (12) | 142 |
C115—H115···F11 | 0.95 | 2.38 | 3.210 (12) | 146 |
C124—H124···Cl71iii | 0.95 | 2.83 | 3.726 (12) | 158 |
C313—H313···F12iv | 0.95 | 2.55 | 3.482 (13) | 167 |
C315—H315···F24v | 0.95 | 2.53 | 3.426 (13) | 158 |
C423—H423···F12vi | 0.95 | 2.40 | 3.296 (14) | 157 |
C18—H18A···Cg1vii | 0.99 | 2.77 | 3.607 (10) | 142 |
C48—H48A···Cg2vi | 0.99 | 2.71 | 3.600 (8) | 150 |
C47—H47B···Cg3vi | 0.99 | 2.82 | 3.693 (10) | 147 |
Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) x, y, z+1; (iii) −x+2, y+1/2, −z+1; (iv) −x+1, y+1/2, −z; (v) x−1, y, z−1; (vi) x−1, y, z; (vii) x+1, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | [Rh(C8H12)(C34H38O6P2)]BF4·CHCl3 |
Mr | 1021.85 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 158 |
a, b, c (Å) | 9.3231 (17), 26.611 (6), 18.218 (4) |
β (°) | 91.596 (7) |
V (Å3) | 4518.0 (16) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.69 |
Crystal size (mm) | 0.9 × 0.4 × 0.04 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (Blessing, 1995) |
Tmin, Tmax | 0.785, 0.973 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19306, 15833, 13832 |
Rint | 0.026 |
(sin θ/λ)max (Å−1) | 0.626 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.150, 1.07 |
No. of reflections | 15833 |
No. of parameters | 645 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0443P)2 + 25.1837P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 0.83, −1.48 |
Absolute structure | Flack (1983), 6332 Friedel pairs |
Absolute structure parameter | 0.05 (3) |
Computer programs: SMART (Siemens, 2001), SMART, SAINT (Siemens, 2001) and SADABS (Sheldrick, 1996), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and Mercury (Bruno et al., 2002), SHELXL97.
Rh1—C12 | 2.227 (8) | Rh1—C16 | 2.291 (9) |
Rh1—C11 | 2.256 (8) | P1—O1 | 1.613 (5) |
Rh1—P2 | 2.257 (2) | P1—C111 | 1.816 (8) |
Rh1—C15 | 2.259 (9) | P2—C211 | 1.795 (7) |
Rh1—P1 | 2.2719 (18) | ||
C12—Rh1—C11 | 35.1 (3) | C45—Rh2—C46 | 33.9 (3) |
Rh1—P1—O1—C21 | −78.0 (5) | Rh2—P3—O3—C31 | −77.7 (5) |
Rh1—P2—O2—C22 | −14.7 (6) | Rh2—P4—O4—C32 | −9.0 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···F23i | 1.03 | 2.39 | 3.402 (17) | 166 |
C8—H8A···F12ii | 1.03 | 2.29 | 3.148 (16) | 139 |
C8—H8A···F14ii | 1.03 | 2.34 | 3.262 (14) | 149 |
C113—H113···F23i | 0.95 | 2.45 | 3.258 (12) | 142 |
C115—H115···F11 | 0.95 | 2.38 | 3.210 (12) | 146 |
C124—H124···Cl71iii | 0.95 | 2.83 | 3.726 (12) | 158 |
C313—H313···F12iv | 0.95 | 2.55 | 3.482 (13) | 167 |
C315—H315···F24v | 0.95 | 2.53 | 3.426 (13) | 158 |
C423—H423···F12vi | 0.95 | 2.40 | 3.296 (14) | 157 |
C18—H18A···Cg1vii | 0.99 | 2.77 | 3.607 (10) | 142 |
C48—H48A···Cg2vi | 0.99 | 2.71 | 3.600 (8) | 150 |
C47—H47B···Cg3vi | 0.99 | 2.82 | 3.693 (10) | 147 |
Symmetry codes: (i) −x+2, y−1/2, −z+1; (ii) x, y, z+1; (iii) −x+2, y+1/2, −z+1; (iv) −x+1, y+1/2, −z; (v) x−1, y, z−1; (vi) x−1, y, z; (vii) x+1, y, z+1. |
This study is part of a programme aimed at developing new catalysts for the asymmetric hydrogenation of alkenes based on carbohydrate precursor molecules (Gainsford et al., 2000; Falshaw et al., 1999, 2007). Only a few structures of related catalysts have been reported [in the following, refcodes in the Cambridge Structural Database (CSD; Version 5.28, updates January 2007; Allen, 2002) are given in capitals]. A preliminary report of this study was given by Gainsford et al. (2005).
The asymmetric unit contains two independent RhI complexes containing the novel ligand CANDYPHOS (CP), BF4- anions and chloroform solvation molecules. Both chloroform molecules show some disorder, which was modelled using two full Cl atoms and two linked positions (approximately 0.5 occupancy each) for the remaining H and Cl atoms. The CP ligands were confirmed to have absolute carbon configurations of SSRRRR (C21–C26, C31–C36). The independent [RhI(CP)(COD)]+ cations (one is shown in Fig. 1) are essentially identical with a close superposition overlap of the final models possible (Fig. 2). The r.m.s. fit of coordinates one to the other was 0.223 Å, with bond and angle r.m.s. values of 0.023 Å and 1.43° (Spek, 2003). Minor orientational differences of the phenyl rings are seen; for example, the O1—P1—C111—C112 and O3—P3—C311—C312 dihedral angles are -117.6 (7) and -112.6 (7)°, respectively.
The seven-membered chelate rings are in the δ-twist-chair conformation (Kadyrov et al., 1999; Anconi et al., 2006). The P-aryl ring conformations are somewhat similar to those reported in QAHZEF (Aghmiz et al., 2004) with α(f), β(r), α' and β' angles [as defined by Seebach et al. (1992) and RajanBabu et al. (1997)] of 15.3 (2) and 16.2 (2), 66.5 (3) and 65.4 (3), 55.0 (3) and 51.5 (3), and 50.0 (3) and 54.1 (3)°, respectively (calculated using PLATON; Spek, 2003). There seems some disparity between reported values in these two reference papers and the deposited coordinates in the CSD, but it is also clear that there is a considerable variation observed in such Rh complexes with angles ranging from 11.2 (QAHZEF) to 75.0° (NIJMUO; RajanBabu et al., 1997). The chiro-inositol rings are closest to chair conformations, with atoms C22 and C32 at the foot and atoms C25 and C35 at the head positions; the displacement Q and θ values (Cremer & Pople, 1975) for the C21–C26 and C31–C36 rings are 0.569 (8) and 0.577 (8) Å and 11.2 (8) and 9.5 (8)°, respectively.
The Rh—P bonds range from 2.255 (2) to 2.2719 (18) Å, within the ranges noted in the closely-related structures ZATSAO {phenyl [2,3-bis(O-diphenylphosphino)-β-D-glucopyranoside-P,P']- [η4-(Z,Z)-cycloocta-1,5-diene]rhodium(I) tetrafluoroborate; 2.250 and 2.275 Å; Kempe et al., 1995}, NIJMUO {(1S,2S)-(η2,η2-cycloocta-1,5-diene)[1,2-bis(diphenylphosphiono)oxy]cyclohexanerhodium(I) hexfluorantimonate benzene solvate; 2.250 and 2.238 Å} and QAHZEF [(η4-(Z,Z)-cycloocta-1,5-diene)-3,4-bis-O-(diphenylphosphino) -1,6-dideoxy-2,5-anhydro-L-iditolrhodium(I) tetrafluoroborate dichloromethane solvate; 2.288–2.311 Å] [please check locations of brackets in compound names; why give the names here when other compounds are cited only by refcode?]. The P—O distances here [average 1.617 (4) Å] are self-consistent and within the range noted in these papers (1.610–1.642 Å).
The Rh—cyclo-1,5-diene bond-distance ranges [2.227 (8)–2.293 (10) Å] are within the ranges observed previously, viz. 2.238–2.317 Å (QOPKEL; Kempe et al., 2001) and 2.219–2.305 Å (POTGEK; Kempe et al., 1998). The octa-1,5-diene (COD) rings have twisted boat conformations (Bats et al., 2004), and are skewed with regard to the RhP2 plane, similar to the configuration observed in, for example, CACNAW (Holz et al., 2001). A CSD survey of related (L)Rh(COD)+ compounds, where L is a bis(phosphine) ligand linked into a seven-membered ring by four atoms (17 hits), shows that the COD-coordinated C atoms are always asymmetrically placed with respect to the RhP2 plane (with bond mid-points out of plane from 0.06 to 0.60 Å (PUHPAJ; Borns et al., 1998). In our case the mid-point of one C═C set is coplanar [the out-of-RhP2-plane values are 0.015 (8) and 0.033 (8) Å], while the other set is 0.355 (8) and 0.248 (8) Å, respectively, from the plane. These values are very similar to those in the bis(phosphine) complex BEDPIJ (Anderson & Pignolet, 1981) and in one of the two cations in QAHZEF; the COD atomic disorder found in this latter study suggests that other close intramolecular interactions may be the cause for the COD rotational skewness observed both here and in other related compounds (e.g. CACNAW).
The crystalline packing is stabilized by weak but significant hydrogen-bonding interactions between the cations and the chloroform and fluoroborate anions (Table 2). The H124···Cl71 interaction, involving the trans-to-P phenyl H atom, has been noted in several compounds [e.g. H···Cl = 2.76 Å and C—H···Cl = 161° in a ruthenium–triphenylphosphine complex (VAKFAP; Snelgrove et al., 2003)]. Interactions between solvent chloroform molecules and tetrafluoroborate anions similar to those reported here have also been observed [e.g. in LUBTAD (Moores et al., 2002), with H···F = 2.34 Å and C—H···F = 171°]. Significant interactions of phenyl H atoms in the meta position with fluoroborate anions (H113, H115, H313 and H315) have been noted in at least ten CSD structures since 2003. The parameters observed in a copper(I) salt (AVEXUU; Fournier et al., 2004) and a ruthenium(I) salt (EWOJAB; Keisham et al., 2004) are H···F distances of 2.38 and 2.37 Å and C—H···F angles of 169 and 153°, respectively. Finally there are at least three C—H···π attractive interactions (the last three entries of Table 2; Cg1, Cg2 and Cg3 are the centres of the phenyl rings C321–C326, C121–C126 and C411–C416, respectively) and a close contact between the methoxy atom O33 and chloroform atom Cl8A at (-x + 1, y + 1/2, -z + 1) [2.930 (9) Å]. Fig. 2 does not show these intermolecular interactions but visually confirms that the estimated potential solvent area of 166 Å (Spek,2 003) is not localized in the lattice.