Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803025005/lh6136sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803025005/lh6136Isup2.hkl |
CCDC reference: 227740
Key indicators
- Single-crystal X-ray study
- T = 218 K
- Mean (C-C) = 0.006 Å
- R factor = 0.029
- wR factor = 0.072
- Data-to-parameter ratio = 14.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.26 Ratio
Author Response: This is probably attibuted to the model used for the treatment of disorder of C34. The ratio of Ueq C34A to Ueq C34 is 0.1273/0.03905 or 3.26. The carbon distances involving C34 and C34A were not fixed and were found to give long and short C-C bond parameters. An alternate model for disorder was attempted where the bond distances of C33-C34, C33-C34A, C34-C35, and C34A-C35 were constrained to 1.48 angstroms. This yielded a rather elongated ellipsoid for C34A, a non-positive definite error for C34A, and a similar number of alert type C's in the CIF check plus an Alert type A. Although the current model is not ideal,we believe that it addresses the issue of disorder for C34. |
PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C35 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... Tm1 PLAT301_ALERT_3_C Main Residue Disorder ......................... 3.00 Perc. PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 21.40 Deg. C34 -C33 -C34A 1.555 1.555 1.555 PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ...... 15.00 Deg. C34A -C35 -C34 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 5 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2001); software used to prepare material for publication: SHELXTL.
[Tm(C4H8O)(C8H8)(C24H25)] | F(000) = 2672 |
Mr = 658.62 | Dx = 1.483 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 6048 reflections |
a = 13.1317 (9) Å | θ = 2.5–28.2° |
b = 15.709 (1) Å | µ = 3.03 mm−1 |
c = 28.594 (2) Å | T = 218 K |
V = 5898.6 (7) Å3 | Block, orange |
Z = 8 | 0.40 × 0.20 × 0.05 mm |
Bruker SMART 4K CCD area-detector diffractometer | 5203 independent reflections |
Radiation source: fine-focus sealed tube | 3903 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = −15→14 |
Tmin = 0.377, Tmax = 0.863 | k = −18→18 |
33690 measured reflections | l = −33→34 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.072 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0334P)2 + 1.0269P] where P = (Fo2 + 2Fc2)/3 |
5203 reflections | (Δ/σ)max = 0.002 |
359 parameters | Δρmax = 0.71 e Å−3 |
0 restraints | Δρmin = −0.43 e Å−3 |
Experimental. A crystal of approximately 0.40 x 0.20 x 0.05 mm3 on an edge was handled under a nitrogen atomosphere and mounted on a glass fiber with Paratone-N oil and then cooled to 218 K. The data were collected on a Bruker Smart 4 K CCD diffractometer with Mo radiation (Bruker,2001). The strucure was solved by direct methods and completed from subsequent difference Fourier syntheses. |
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) | |
O1 | 0.8828 (2) | 0.30732 (17) | 0.38686 (10) | 0.0420 (8) | |
Tm1 | 0.956870 (13) | 0.172882 (10) | 0.386912 (6) | 0.02965 (8) | |
C1 | 0.8891 (4) | 0.0841 (3) | 0.45381 (17) | 0.0485 (12) | |
H1A | 0.8928 | 0.0905 | 0.4864 | 0.073* | |
C2 | 0.8007 (4) | 0.1215 (3) | 0.4347 (2) | 0.0530 (13) | |
H2A | 0.7554 | 0.1424 | 0.4575 | 0.079* | |
C3 | 0.7665 (3) | 0.1340 (3) | 0.3887 (2) | 0.0561 (14) | |
H3A | 0.7022 | 0.1602 | 0.3878 | 0.084* | |
C4 | 0.8040 (4) | 0.1175 (3) | 0.3435 (2) | 0.0593 (15) | |
H4A | 0.7619 | 0.1393 | 0.3198 | 0.089* | |
C5 | 0.8902 (4) | 0.0756 (3) | 0.32611 (18) | 0.0554 (14) | |
H5A | 0.8936 | 0.0771 | 0.2933 | 0.083* | |
C6 | 0.9723 (3) | 0.0322 (3) | 0.34598 (18) | 0.0450 (12) | |
H6A | 1.0147 | 0.0071 | 0.3234 | 0.067* | |
C7 | 1.0058 (4) | 0.0173 (3) | 0.39117 (18) | 0.0449 (12) | |
H7A | 1.0654 | −0.0158 | 0.3920 | 0.067* | |
C8 | 0.9723 (3) | 0.0398 (3) | 0.43562 (18) | 0.0439 (12) | |
H8A | 1.0165 | 0.0204 | 0.4592 | 0.066* | |
C9 | 1.1077 (3) | 0.2469 (2) | 0.35766 (14) | 0.0271 (9) | |
C10 | 1.1477 (3) | 0.2611 (2) | 0.31231 (14) | 0.0279 (9) | |
C11 | 1.2289 (3) | 0.3153 (2) | 0.30462 (16) | 0.0392 (11) | |
H11A | 1.2533 | 0.3234 | 0.2740 | 0.047* | |
C12 | 1.2745 (3) | 0.3577 (3) | 0.34111 (17) | 0.0423 (11) | |
H12A | 1.3294 | 0.3947 | 0.3353 | 0.051* | |
C13 | 1.2399 (3) | 0.3460 (3) | 0.38595 (16) | 0.0402 (11) | |
H13A | 1.2711 | 0.3748 | 0.4110 | 0.048* | |
C14 | 1.1578 (3) | 0.2908 (2) | 0.39422 (14) | 0.0292 (9) | |
C15 | 1.1218 (3) | 0.2761 (2) | 0.44269 (14) | 0.0312 (9) | |
C16 | 1.1429 (3) | 0.1993 (2) | 0.46567 (15) | 0.0323 (10) | |
C17 | 1.1016 (3) | 0.1839 (3) | 0.50975 (16) | 0.0393 (11) | |
H17A | 1.1144 | 0.1314 | 0.5243 | 0.047* | |
C18 | 1.0426 (3) | 0.2432 (3) | 0.53267 (16) | 0.0387 (10) | |
C19 | 1.0271 (3) | 0.3204 (3) | 0.51094 (16) | 0.0416 (11) | |
H19A | 0.9889 | 0.3622 | 0.5267 | 0.050* | |
C20 | 1.0650 (3) | 0.3391 (2) | 0.46709 (16) | 0.0366 (10) | |
C21 | 1.2159 (3) | 0.1354 (3) | 0.44494 (16) | 0.0450 (11) | |
H21A | 1.2846 | 0.1582 | 0.4460 | 0.068* | |
H21B | 1.1971 | 0.1240 | 0.4127 | 0.068* | |
H21C | 1.2131 | 0.0829 | 0.4628 | 0.068* | |
C22 | 0.9990 (4) | 0.2256 (3) | 0.58031 (17) | 0.0554 (13) | |
H22A | 0.9991 | 0.1647 | 0.5860 | 0.083* | |
H22B | 0.9297 | 0.2469 | 0.5818 | 0.083* | |
H22C | 1.0401 | 0.2538 | 0.6039 | 0.083* | |
C23 | 1.0488 (4) | 0.4256 (3) | 0.44534 (17) | 0.0536 (13) | |
H23A | 0.9913 | 0.4534 | 0.4603 | 0.080* | |
H23B | 1.0351 | 0.4191 | 0.4122 | 0.080* | |
H23C | 1.1094 | 0.4600 | 0.4496 | 0.080* | |
C24 | 1.1027 (3) | 0.2149 (2) | 0.27134 (14) | 0.0295 (9) | |
C25 | 1.0370 (3) | 0.2546 (3) | 0.23967 (15) | 0.0327 (9) | |
C26 | 0.9922 (3) | 0.2063 (3) | 0.20384 (15) | 0.0378 (10) | |
H26A | 0.9460 | 0.2329 | 0.1834 | 0.045* | |
C27 | 1.0139 (3) | 0.1212 (3) | 0.19766 (15) | 0.0371 (10) | |
C28 | 1.0843 (3) | 0.0848 (2) | 0.22769 (16) | 0.0376 (11) | |
H28A | 1.1019 | 0.0273 | 0.2233 | 0.045* | |
C29 | 1.1292 (3) | 0.1288 (2) | 0.26351 (14) | 0.0332 (10) | |
C30 | 1.0158 (3) | 0.3490 (2) | 0.24163 (17) | 0.0414 (11) | |
H30A | 1.0383 | 0.3714 | 0.2715 | 0.062* | |
H30B | 0.9432 | 0.3588 | 0.2381 | 0.062* | |
H30C | 1.0521 | 0.3774 | 0.2165 | 0.062* | |
C31 | 0.9672 (3) | 0.0710 (3) | 0.15780 (17) | 0.0536 (13) | |
H31A | 0.9111 | 0.1030 | 0.1445 | 0.080* | |
H31B | 0.9423 | 0.0169 | 0.1695 | 0.080* | |
H31C | 1.0183 | 0.0611 | 0.1339 | 0.080* | |
C32 | 1.2104 (3) | 0.0875 (3) | 0.29296 (16) | 0.0455 (12) | |
H32A | 1.2222 | 0.0299 | 0.2819 | 0.068* | |
H32B | 1.1883 | 0.0859 | 0.3253 | 0.068* | |
H32C | 1.2730 | 0.1200 | 0.2906 | 0.068* | |
C33 | 0.8058 (4) | 0.3437 (3) | 0.41729 (19) | 0.0539 (13) | |
H33A | 0.7533 | 0.3009 | 0.4239 | 0.065* | |
H33B | 0.8370 | 0.3605 | 0.4470 | 0.065* | |
C34 | 0.761 (2) | 0.4147 (12) | 0.3961 (12) | 0.067 (6) | 0.60 (6) |
H34A | 0.8001 | 0.4668 | 0.4020 | 0.080* | 0.60 (6) |
H34B | 0.6905 | 0.4228 | 0.4061 | 0.080* | 0.60 (6) |
C34A | 0.743 (3) | 0.397 (3) | 0.3806 (11) | 0.080 (11) | 0.40 (6) |
H34C | 0.6710 | 0.3818 | 0.3837 | 0.097* | 0.40 (6) |
H34D | 0.7504 | 0.4571 | 0.3879 | 0.097* | 0.40 (6) |
C35 | 0.7683 (4) | 0.3853 (4) | 0.3411 (3) | 0.089 (2) | |
H35A | 0.7148 | 0.3444 | 0.3330 | 0.107* | |
H35B | 0.7647 | 0.4342 | 0.3199 | 0.107* | |
C36 | 0.8718 (4) | 0.3449 (3) | 0.34061 (19) | 0.0562 (13) | |
H36A | 0.8761 | 0.3011 | 0.3163 | 0.067* | |
H36B | 0.9249 | 0.3875 | 0.3350 | 0.067* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0432 (18) | 0.0340 (15) | 0.049 (2) | 0.0094 (13) | 0.0129 (16) | 0.0063 (14) |
Tm1 | 0.02790 (11) | 0.02567 (10) | 0.03538 (13) | −0.00214 (7) | 0.00180 (9) | 0.00325 (8) |
C1 | 0.061 (3) | 0.043 (2) | 0.042 (3) | −0.008 (2) | 0.010 (3) | 0.009 (2) |
C2 | 0.048 (3) | 0.043 (3) | 0.067 (4) | −0.008 (2) | 0.024 (3) | 0.004 (3) |
C3 | 0.026 (2) | 0.046 (3) | 0.096 (5) | −0.004 (2) | 0.000 (3) | 0.009 (3) |
C4 | 0.051 (3) | 0.060 (3) | 0.066 (4) | −0.020 (3) | −0.026 (3) | 0.025 (3) |
C5 | 0.068 (4) | 0.051 (3) | 0.048 (3) | −0.030 (3) | −0.007 (3) | −0.002 (2) |
C6 | 0.058 (3) | 0.032 (2) | 0.045 (3) | −0.013 (2) | 0.006 (3) | −0.004 (2) |
C7 | 0.048 (3) | 0.029 (2) | 0.058 (4) | 0.001 (2) | 0.009 (2) | 0.000 (2) |
C8 | 0.046 (3) | 0.037 (2) | 0.048 (3) | −0.0037 (19) | −0.009 (2) | 0.013 (2) |
C9 | 0.025 (2) | 0.0238 (18) | 0.033 (3) | 0.0012 (16) | −0.0008 (18) | 0.0036 (17) |
C10 | 0.030 (2) | 0.0277 (19) | 0.026 (2) | 0.0023 (16) | 0.0013 (18) | 0.0048 (17) |
C11 | 0.040 (2) | 0.044 (2) | 0.034 (3) | −0.009 (2) | 0.004 (2) | 0.003 (2) |
C12 | 0.038 (2) | 0.043 (2) | 0.046 (3) | −0.0141 (19) | 0.007 (2) | 0.006 (2) |
C13 | 0.040 (3) | 0.038 (2) | 0.042 (3) | −0.0114 (19) | −0.004 (2) | −0.006 (2) |
C14 | 0.034 (2) | 0.0302 (19) | 0.024 (2) | −0.0012 (17) | 0.0017 (18) | 0.0031 (18) |
C15 | 0.030 (2) | 0.037 (2) | 0.026 (2) | −0.0046 (17) | −0.004 (2) | −0.0042 (18) |
C16 | 0.033 (2) | 0.035 (2) | 0.030 (3) | −0.0047 (17) | −0.005 (2) | 0.0023 (18) |
C17 | 0.043 (3) | 0.038 (2) | 0.037 (3) | −0.0052 (19) | −0.009 (2) | 0.011 (2) |
C18 | 0.040 (2) | 0.044 (2) | 0.032 (3) | −0.008 (2) | −0.001 (2) | −0.001 (2) |
C19 | 0.049 (3) | 0.038 (2) | 0.038 (3) | −0.002 (2) | 0.005 (2) | −0.010 (2) |
C20 | 0.043 (3) | 0.036 (2) | 0.031 (3) | −0.0039 (18) | 0.000 (2) | −0.0038 (19) |
C21 | 0.042 (3) | 0.048 (2) | 0.045 (3) | 0.006 (2) | −0.001 (2) | 0.007 (2) |
C22 | 0.069 (3) | 0.060 (3) | 0.038 (3) | −0.009 (3) | 0.010 (3) | 0.005 (3) |
C23 | 0.076 (4) | 0.037 (2) | 0.048 (3) | 0.005 (2) | 0.008 (3) | −0.002 (2) |
C24 | 0.030 (2) | 0.035 (2) | 0.024 (2) | −0.0036 (17) | 0.0080 (18) | 0.0040 (18) |
C25 | 0.036 (2) | 0.037 (2) | 0.025 (2) | 0.0010 (19) | 0.006 (2) | 0.0039 (18) |
C26 | 0.040 (2) | 0.047 (2) | 0.026 (3) | 0.003 (2) | 0.004 (2) | −0.001 (2) |
C27 | 0.040 (3) | 0.043 (2) | 0.028 (3) | −0.0039 (19) | 0.011 (2) | −0.006 (2) |
C28 | 0.044 (3) | 0.028 (2) | 0.041 (3) | 0.0000 (18) | 0.011 (2) | −0.005 (2) |
C29 | 0.037 (2) | 0.031 (2) | 0.032 (3) | 0.0017 (18) | 0.009 (2) | 0.0031 (19) |
C30 | 0.049 (3) | 0.038 (2) | 0.038 (3) | 0.004 (2) | −0.003 (2) | 0.004 (2) |
C31 | 0.063 (3) | 0.055 (3) | 0.042 (3) | −0.007 (2) | −0.005 (3) | −0.018 (3) |
C32 | 0.049 (3) | 0.041 (2) | 0.046 (3) | 0.010 (2) | 0.000 (2) | −0.001 (2) |
C33 | 0.053 (3) | 0.052 (3) | 0.057 (4) | 0.014 (2) | 0.018 (3) | −0.006 (3) |
C34 | 0.082 (12) | 0.039 (7) | 0.080 (16) | 0.023 (6) | 0.037 (11) | 0.010 (8) |
C34A | 0.076 (15) | 0.13 (3) | 0.038 (15) | 0.077 (17) | −0.004 (12) | −0.003 (13) |
C35 | 0.076 (4) | 0.096 (5) | 0.094 (6) | 0.047 (4) | 0.012 (4) | 0.040 (4) |
C36 | 0.062 (3) | 0.049 (3) | 0.057 (3) | 0.015 (2) | 0.013 (3) | 0.014 (3) |
O1—C33 | 1.451 (5) | C19—C20 | 1.381 (6) |
O1—C36 | 1.455 (5) | C19—H19A | 0.9400 |
O1—Tm1 | 2.325 (3) | C20—C23 | 1.510 (6) |
Tm1—C9 | 2.445 (4) | C21—H21A | 0.9700 |
Tm1—C5 | 2.475 (4) | C21—H21B | 0.9700 |
Tm1—C6 | 2.509 (4) | C21—H21C | 0.9700 |
Tm1—C4 | 2.515 (5) | C22—H22A | 0.9700 |
Tm1—C8 | 2.520 (4) | C22—H22B | 0.9700 |
Tm1—C1 | 2.529 (4) | C22—H22C | 0.9700 |
Tm1—C7 | 2.530 (4) | C23—H23A | 0.9700 |
Tm1—C3 | 2.573 (4) | C23—H23B | 0.9700 |
Tm1—C2 | 2.594 (4) | C23—H23C | 0.9700 |
C1—C8 | 1.396 (6) | C24—C25 | 1.397 (5) |
C1—C2 | 1.410 (7) | C24—C29 | 1.414 (5) |
C1—H1A | 0.9400 | C25—C26 | 1.403 (6) |
C2—C3 | 1.406 (7) | C25—C30 | 1.511 (5) |
C2—H2A | 0.9400 | C26—C27 | 1.378 (6) |
C3—C4 | 1.405 (7) | C26—H26A | 0.9400 |
C3—H3A | 0.9400 | C27—C28 | 1.385 (6) |
C4—C5 | 1.401 (7) | C27—C31 | 1.516 (6) |
C4—H4A | 0.9400 | C28—C29 | 1.370 (6) |
C5—C6 | 1.396 (7) | C28—H28A | 0.9400 |
C5—H5A | 0.9400 | C29—C32 | 1.506 (6) |
C6—C7 | 1.385 (6) | C30—H30A | 0.9700 |
C6—H6A | 0.9400 | C30—H30B | 0.9700 |
C7—C8 | 1.391 (6) | C30—H30C | 0.9700 |
C7—H7A | 0.9400 | C31—H31A | 0.9700 |
C8—H8A | 0.9400 | C31—H31B | 0.9700 |
C9—C14 | 1.415 (5) | C31—H31C | 0.9700 |
C9—C10 | 1.416 (5) | C32—H32A | 0.9700 |
C10—C11 | 1.383 (5) | C32—H32B | 0.9700 |
C10—C24 | 1.499 (5) | C32—H32C | 0.9700 |
C11—C12 | 1.375 (6) | C33—C34 | 1.40 (2) |
C11—H11A | 0.9400 | C33—C34A | 1.57 (3) |
C12—C13 | 1.373 (6) | C33—H33A | 0.9800 |
C12—H12A | 0.9400 | C33—H33B | 0.9800 |
C13—C14 | 1.404 (6) | C34—C35 | 1.64 (4) |
C13—H13A | 0.9400 | C34—H34A | 0.9800 |
C14—C15 | 1.483 (5) | C34—H34B | 0.9800 |
C15—C16 | 1.402 (5) | C34A—C35 | 1.19 (3) |
C15—C20 | 1.422 (5) | C34A—H34C | 0.9800 |
C16—C17 | 1.393 (6) | C34A—H34D | 0.9800 |
C16—C21 | 1.510 (6) | C35—C36 | 1.500 (7) |
C17—C18 | 1.377 (6) | C35—H35A | 0.9800 |
C17—H17A | 0.9400 | C35—H35B | 0.9800 |
C18—C19 | 1.378 (6) | C36—H36A | 0.9800 |
C18—C22 | 1.503 (6) | C36—H36B | 0.9800 |
C33—O1—C36 | 108.5 (3) | C13—C14—C15 | 119.9 (4) |
C33—O1—Tm1 | 130.4 (3) | C9—C14—C15 | 117.8 (3) |
C36—O1—Tm1 | 114.2 (2) | C16—C15—C20 | 118.2 (4) |
O1—Tm1—C9 | 84.66 (10) | C16—C15—C14 | 120.6 (4) |
O1—Tm1—C5 | 114.35 (15) | C20—C15—C14 | 121.2 (4) |
C9—Tm1—C5 | 109.88 (15) | C17—C16—C15 | 119.8 (4) |
O1—Tm1—C6 | 146.46 (14) | C17—C16—C21 | 119.2 (4) |
C9—Tm1—C6 | 101.20 (13) | C15—C16—C21 | 120.9 (4) |
C5—Tm1—C6 | 32.53 (16) | C18—C17—C16 | 122.2 (4) |
O1—Tm1—C4 | 88.86 (15) | C18—C17—H17A | 118.9 |
C9—Tm1—C4 | 130.00 (17) | C16—C17—H17A | 118.9 |
C5—Tm1—C4 | 32.59 (18) | C17—C18—C19 | 117.6 (4) |
C6—Tm1—C4 | 61.92 (17) | C17—C18—C22 | 121.4 (4) |
O1—Tm1—C8 | 141.94 (14) | C19—C18—C22 | 120.9 (4) |
C9—Tm1—C8 | 121.24 (13) | C18—C19—C20 | 122.9 (4) |
C5—Tm1—C8 | 84.51 (16) | C18—C19—H19A | 118.6 |
C6—Tm1—C8 | 61.35 (16) | C20—C19—H19A | 118.6 |
C4—Tm1—C8 | 92.83 (14) | C19—C20—C15 | 119.2 (4) |
O1—Tm1—C1 | 110.72 (13) | C19—C20—C23 | 120.9 (4) |
C9—Tm1—C1 | 143.74 (15) | C15—C20—C23 | 119.9 (4) |
C5—Tm1—C1 | 93.81 (16) | C16—C21—H21A | 109.5 |
C6—Tm1—C1 | 84.00 (15) | C16—C21—H21B | 109.5 |
C4—Tm1—C1 | 84.32 (17) | H21A—C21—H21B | 109.5 |
C8—Tm1—C1 | 32.11 (15) | C16—C21—H21C | 109.5 |
O1—Tm1—C7 | 169.63 (13) | H21A—C21—H21C | 109.5 |
C9—Tm1—C7 | 105.68 (13) | H21B—C21—H21C | 109.5 |
C5—Tm1—C7 | 61.78 (17) | C18—C22—H22A | 109.5 |
C6—Tm1—C7 | 31.90 (14) | C18—C22—H22B | 109.5 |
C4—Tm1—C7 | 83.80 (16) | H22A—C22—H22B | 109.5 |
C8—Tm1—C7 | 31.96 (15) | C18—C22—H22C | 109.5 |
C1—Tm1—C7 | 61.34 (15) | H22A—C22—H22C | 109.5 |
O1—Tm1—C3 | 78.98 (13) | H22B—C22—H22C | 109.5 |
C9—Tm1—C3 | 155.02 (16) | C20—C23—H23A | 109.5 |
C5—Tm1—C3 | 61.55 (18) | C20—C23—H23B | 109.5 |
C6—Tm1—C3 | 83.02 (16) | H23A—C23—H23B | 109.5 |
C4—Tm1—C3 | 32.03 (17) | C20—C23—H23C | 109.5 |
C8—Tm1—C3 | 82.57 (15) | H23A—C23—H23C | 109.5 |
C1—Tm1—C3 | 60.83 (17) | H23B—C23—H23C | 109.5 |
C7—Tm1—C3 | 90.96 (15) | C25—C24—C29 | 118.4 (4) |
O1—Tm1—C2 | 87.23 (12) | C25—C24—C10 | 122.3 (3) |
C9—Tm1—C2 | 165.71 (15) | C29—C24—C10 | 119.3 (4) |
C5—Tm1—C2 | 84.19 (17) | C24—C25—C26 | 119.4 (4) |
C6—Tm1—C2 | 92.05 (14) | C24—C25—C30 | 121.8 (4) |
C4—Tm1—C2 | 61.40 (19) | C26—C25—C30 | 118.7 (4) |
C8—Tm1—C2 | 60.93 (15) | C27—C26—C25 | 122.1 (4) |
C1—Tm1—C2 | 31.93 (15) | C27—C26—H26A | 119.0 |
C7—Tm1—C2 | 82.83 (15) | C25—C26—H26A | 119.0 |
C3—Tm1—C2 | 31.58 (17) | C26—C27—C28 | 117.3 (4) |
C8—C1—C2 | 135.1 (5) | C26—C27—C31 | 121.1 (4) |
C8—C1—Tm1 | 73.6 (3) | C28—C27—C31 | 121.4 (4) |
C2—C1—Tm1 | 76.6 (3) | C29—C28—C27 | 122.8 (4) |
C8—C1—H1A | 112.5 | C29—C28—H28A | 118.6 |
C2—C1—H1A | 112.5 | C27—C28—H28A | 118.6 |
Tm1—C1—H1A | 132.3 | C28—C29—C24 | 119.7 (4) |
C3—C2—C1 | 133.1 (5) | C28—C29—C32 | 120.4 (4) |
C3—C2—Tm1 | 73.4 (3) | C24—C29—C32 | 119.9 (4) |
C1—C2—Tm1 | 71.5 (3) | C25—C30—H30A | 109.5 |
C3—C2—H2A | 113.5 | C25—C30—H30B | 109.5 |
C1—C2—H2A | 113.5 | H30A—C30—H30B | 109.5 |
Tm1—C2—H2A | 139.2 | C25—C30—H30C | 109.5 |
C4—C3—C2 | 136.3 (5) | H30A—C30—H30C | 109.5 |
C4—C3—Tm1 | 71.7 (3) | H30B—C30—H30C | 109.5 |
C2—C3—Tm1 | 75.0 (3) | C27—C31—H31A | 109.5 |
C4—C3—H3A | 111.9 | C27—C31—H31B | 109.5 |
C2—C3—H3A | 111.9 | H31A—C31—H31B | 109.5 |
Tm1—C3—H3A | 140.3 | C27—C31—H31C | 109.5 |
C5—C4—C3 | 134.2 (5) | H31A—C31—H31C | 109.5 |
C5—C4—Tm1 | 72.1 (3) | H31B—C31—H31C | 109.5 |
C3—C4—Tm1 | 76.3 (3) | C29—C32—H32A | 109.5 |
C5—C4—H4A | 112.9 | C29—C32—H32B | 109.5 |
C3—C4—H4A | 112.9 | H32A—C32—H32B | 109.5 |
Tm1—C4—H4A | 134.4 | C29—C32—H32C | 109.5 |
C6—C5—C4 | 135.1 (5) | H32A—C32—H32C | 109.5 |
C6—C5—Tm1 | 75.1 (3) | H32B—C32—H32C | 109.5 |
C4—C5—Tm1 | 75.3 (3) | C34—C33—O1 | 110.2 (12) |
C6—C5—H5A | 112.5 | C34—C33—C34A | 21.4 (15) |
C4—C5—H5A | 112.5 | O1—C33—C34A | 99.9 (12) |
Tm1—C5—H5A | 132.0 | C34—C33—H33A | 109.6 |
C7—C6—C5 | 135.0 (5) | O1—C33—H33A | 109.6 |
C7—C6—Tm1 | 74.9 (3) | C34A—C33—H33A | 97.1 |
C5—C6—Tm1 | 72.4 (3) | C34—C33—H33B | 109.6 |
C7—C6—H6A | 112.5 | O1—C33—H33B | 109.6 |
C5—C6—H6A | 112.5 | C34A—C33—H33B | 130.9 |
Tm1—C6—H6A | 137.5 | H33A—C33—H33B | 108.1 |
C6—C7—C8 | 135.2 (4) | C33—C34—C35 | 99.6 (15) |
C6—C7—Tm1 | 73.2 (2) | C33—C34—H34A | 111.9 |
C8—C7—Tm1 | 73.6 (2) | C35—C34—H34A | 111.9 |
C6—C7—H7A | 112.4 | C33—C34—H34B | 111.9 |
C8—C7—H7A | 112.4 | C35—C34—H34B | 111.9 |
Tm1—C7—H7A | 138.4 | H34A—C34—H34B | 109.6 |
C7—C8—C1 | 135.6 (4) | C35—C34A—C33 | 114 (2) |
C7—C8—Tm1 | 74.4 (3) | C35—C34A—H34C | 108.7 |
C1—C8—Tm1 | 74.3 (2) | C33—C34A—H34C | 108.7 |
C7—C8—H8A | 112.2 | C35—C34A—H34D | 108.7 |
C1—C8—H8A | 112.2 | C33—C34A—H34D | 108.7 |
Tm1—C8—H8A | 135.6 | H34C—C34A—H34D | 107.6 |
C14—C9—C10 | 115.3 (3) | C34A—C35—C36 | 108.8 (17) |
C14—C9—Tm1 | 110.8 (3) | C34A—C35—C34 | 15 (3) |
C10—C9—Tm1 | 133.5 (3) | C36—C35—C34 | 100.4 (10) |
C11—C10—C9 | 121.9 (4) | C34A—C35—H35A | 97.0 |
C11—C10—C24 | 118.5 (4) | C36—C35—H35A | 111.7 |
C9—C10—C24 | 119.6 (3) | C34—C35—H35A | 111.7 |
C12—C11—C10 | 120.9 (4) | C34A—C35—H35B | 117.3 |
C12—C11—H11A | 119.5 | C36—C35—H35B | 111.7 |
C10—C11—H11A | 119.5 | C34—C35—H35B | 111.7 |
C13—C12—C11 | 120.0 (4) | H35A—C35—H35B | 109.5 |
C13—C12—H12A | 120.0 | O1—C36—C35 | 104.6 (4) |
C11—C12—H12A | 120.0 | O1—C36—H36A | 110.8 |
C12—C13—C14 | 119.6 (4) | C35—C36—H36A | 110.8 |
C12—C13—H13A | 120.2 | O1—C36—H36B | 110.8 |
C14—C13—H13A | 120.2 | C35—C36—H36B | 110.8 |
C13—C14—C9 | 122.3 (4) | H36A—C36—H36B | 108.9 |