Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804013595/lh6225sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804013595/lh6225Isup2.hkl |
CCDC reference: 245289
Key indicators
- Single-crystal X-ray study
- T = 198 K
- Mean (C-C) = 0.004 Å
- R factor = 0.053
- wR factor = 0.160
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 48 Perc. PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.85 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C32 - C33 .. 5.72 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C56 - C57 .. 5.59 su PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C31 PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C48 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C32 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C46 PLAT242_ALERT_2_C Check Low U(eq) as Compared to Neighbors .... C53 PLAT410_ALERT_2_C Short Intra H...H Contact H28B .. H31B .. 1.96 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 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 9 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, 1997–1999); cell refinement: SMART; data reduction: SAINT (Bruker, 1997–1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997b); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997b); molecular graphics: PLATON (Spek, 2004); software used to prepare material for publication: SHELXTL (Sheldrick, 1997a).
C58H48O6 | F(000) = 3552 |
Mr = 840.96 | Dx = 1.233 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 14515 reflections |
a = 18.1209 (13) Å | θ = 2.1–25.0° |
b = 19.8137 (14) Å | µ = 0.08 mm−1 |
c = 25.2396 (17) Å | T = 198 K |
V = 9062.1 (11) Å3 | Irregular, colourless |
Z = 8 | 0.4 × 0.4 × 0.3 mm |
Bruker SMART 1000/P4 diffractometer | 10340 independent reflections |
Radiation source: fine-focus sealed tube | 5000 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.067 |
ω and φ scans | θmax = 27.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −23→21 |
Tmin = 0.88, Tmax = 0.98 | k = −24→25 |
60976 measured reflections | l = −32→32 |
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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0729P)2] where P = (Fo2 + 2Fc2)/3 |
10340 reflections | (Δ/σ)max < 0.001 |
577 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.23 e Å−3 |
Experimental. Crystal decay was monitored by repeating the initial 50 frames at the end of the data collection and analyzing duplicate reflections. 1H NMR spectra (300.15 MHz) were acquired on a Bruker AC-300 spectrometer using the solvent as chemical shift standard. Electronic ionization mass spectra were acquired on a VG Instruments ZAB-IF spectrometer at a potential of 70 eV. |
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 | ||
C1 | 0.12535 (12) | 0.14430 (11) | 0.71632 (8) | 0.0404 (5) | |
C2 | 0.19778 (12) | 0.12053 (10) | 0.72030 (7) | 0.0383 (5) | |
C3 | 0.24536 (12) | 0.14107 (10) | 0.76145 (7) | 0.0381 (5) | |
C4 | 0.21628 (12) | 0.18011 (10) | 0.80181 (8) | 0.0391 (5) | |
H4 | 0.2471 | 0.1939 | 0.8303 | 0.047* | |
C5 | 0.14216 (12) | 0.19958 (10) | 0.80125 (8) | 0.0393 (5) | |
C6 | 0.09877 (12) | 0.18285 (11) | 0.75787 (8) | 0.0418 (5) | |
H6 | 0.0492 | 0.1984 | 0.7567 | 0.050* | |
C7 | 0.32683 (12) | 0.12645 (11) | 0.75670 (8) | 0.0437 (5) | |
H7A | 0.3345 | 0.0781 | 0.7484 | 0.052* | |
H7B | 0.3518 | 0.1364 | 0.7907 | 0.052* | |
C8 | 0.35951 (11) | 0.16999 (11) | 0.71287 (8) | 0.0394 (5) | |
C9 | 0.39857 (11) | 0.14196 (10) | 0.67020 (8) | 0.0375 (5) | |
C10 | 0.42125 (11) | 0.18074 (11) | 0.62711 (8) | 0.0396 (5) | |
C11 | 0.40396 (12) | 0.24937 (12) | 0.62761 (9) | 0.0474 (6) | |
H11 | 0.4172 | 0.2766 | 0.5981 | 0.057* | |
C12 | 0.36814 (13) | 0.27841 (12) | 0.66991 (10) | 0.0534 (6) | |
H12 | 0.3589 | 0.3256 | 0.6701 | 0.064* | |
C13 | 0.34581 (12) | 0.23917 (11) | 0.71180 (9) | 0.0480 (6) | |
H13 | 0.3205 | 0.2596 | 0.7406 | 0.058* | |
C14 | 0.45963 (12) | 0.15039 (12) | 0.57919 (8) | 0.0456 (6) | |
H14A | 0.5090 | 0.1710 | 0.5749 | 0.055* | |
H14B | 0.4662 | 0.1012 | 0.5845 | 0.055* | |
C15 | 0.41395 (12) | 0.16295 (11) | 0.52992 (8) | 0.0402 (5) | |
C16 | 0.34327 (12) | 0.13594 (10) | 0.52456 (7) | 0.0390 (5) | |
C17 | 0.29328 (12) | 0.15824 (11) | 0.48572 (7) | 0.0397 (5) | |
C18 | 0.31869 (12) | 0.20448 (11) | 0.44881 (8) | 0.0433 (5) | |
H18 | 0.2864 | 0.2199 | 0.4218 | 0.052* | |
C19 | 0.39053 (12) | 0.22878 (11) | 0.45062 (8) | 0.0421 (5) | |
C20 | 0.43687 (12) | 0.20878 (11) | 0.49136 (8) | 0.0432 (5) | |
H20 | 0.4854 | 0.2267 | 0.4931 | 0.052* | |
C21 | 0.21360 (12) | 0.13619 (12) | 0.48794 (8) | 0.0452 (6) | |
H21A | 0.2111 | 0.0868 | 0.4935 | 0.054* | |
H21B | 0.1891 | 0.1468 | 0.4539 | 0.054* | |
C22 | 0.17393 (12) | 0.17203 (11) | 0.53276 (8) | 0.0416 (5) | |
C23 | 0.14164 (11) | 0.13670 (11) | 0.57523 (8) | 0.0392 (5) | |
C24 | 0.11286 (11) | 0.17062 (12) | 0.61924 (8) | 0.0423 (5) | |
C25 | 0.11551 (12) | 0.24040 (13) | 0.61963 (9) | 0.0518 (6) | |
H25 | 0.0979 | 0.2642 | 0.6498 | 0.062* | |
C26 | 0.14336 (13) | 0.27641 (13) | 0.57695 (10) | 0.0578 (7) | |
H26 | 0.1423 | 0.3243 | 0.5770 | 0.069* | |
C27 | 0.17258 (13) | 0.24170 (13) | 0.53455 (9) | 0.0522 (6) | |
H27 | 0.1924 | 0.2665 | 0.5056 | 0.063* | |
C28 | 0.07982 (12) | 0.13327 (12) | 0.66663 (8) | 0.0454 (6) | |
H28A | 0.0288 | 0.1494 | 0.6728 | 0.054* | |
H28B | 0.0775 | 0.0844 | 0.6587 | 0.054* | |
C29 | 0.11020 (14) | 0.23900 (12) | 0.84468 (10) | 0.0511 (6) | |
H29 | 0.0600 | 0.2520 | 0.8412 | 0.061* | |
O29 | 0.14175 (10) | 0.25651 (9) | 0.88449 (7) | 0.0661 (5) | |
C30 | 0.41828 (14) | 0.27670 (12) | 0.41142 (10) | 0.0557 (6) | |
H30 | 0.4678 | 0.2915 | 0.4155 | 0.067* | |
O30 | 0.38428 (11) | 0.29928 (10) | 0.37443 (7) | 0.0761 (6) | |
C31 | 0.20064 (17) | 0.01175 (12) | 0.67869 (9) | 0.0643 (7) | |
H31A | 0.2155 | −0.0079 | 0.6442 | 0.077* | |
H31B | 0.1460 | 0.0127 | 0.6796 | 0.077* | |
O31 | 0.22764 (8) | 0.08096 (8) | 0.68124 (5) | 0.0486 (4) | |
C32 | 0.22718 (13) | −0.03360 (11) | 0.72177 (8) | 0.0454 (6) | |
C33 | 0.19304 (14) | −0.03389 (13) | 0.77070 (10) | 0.0602 (7) | |
H33 | 0.1551 | −0.0021 | 0.7778 | 0.072* | |
C34 | 0.21298 (17) | −0.07943 (15) | 0.80944 (11) | 0.0687 (8) | |
H34 | 0.1897 | −0.0780 | 0.8431 | 0.082* | |
C35 | 0.26585 (17) | −0.12629 (14) | 0.79954 (12) | 0.0679 (8) | |
H35 | 0.2780 | −0.1589 | 0.8257 | 0.081* | |
C36 | 0.30102 (17) | −0.12638 (14) | 0.75252 (14) | 0.0787 (9) | |
H36 | 0.3388 | −0.1586 | 0.7459 | 0.094* | |
C37 | 0.28247 (16) | −0.07979 (14) | 0.71360 (11) | 0.0683 (8) | |
H37 | 0.3084 | −0.0799 | 0.6809 | 0.082* | |
C38 | 0.47791 (12) | 0.05703 (11) | 0.70093 (9) | 0.0471 (6) | |
H38A | 0.4707 | 0.0719 | 0.7380 | 0.056* | |
H38B | 0.5211 | 0.0813 | 0.6863 | 0.056* | |
O38 | 0.41352 (7) | 0.07286 (7) | 0.67031 (5) | 0.0393 (4) | |
C39 | 0.49172 (12) | −0.01724 (11) | 0.69951 (9) | 0.0433 (5) | |
C40 | 0.49438 (13) | −0.05461 (13) | 0.74579 (10) | 0.0570 (6) | |
H40 | 0.4843 | −0.0332 | 0.7787 | 0.068* | |
C41 | 0.51130 (16) | −0.12192 (15) | 0.74488 (13) | 0.0758 (8) | |
H41 | 0.5138 | −0.1465 | 0.7771 | 0.091* | |
C42 | 0.52457 (16) | −0.15386 (15) | 0.69815 (14) | 0.0773 (8) | |
H42 | 0.5367 | −0.2005 | 0.6978 | 0.093* | |
C43 | 0.52032 (17) | −0.11826 (15) | 0.65145 (12) | 0.0739 (8) | |
H43 | 0.5283 | −0.1404 | 0.6186 | 0.089* | |
C44 | 0.50432 (14) | −0.04994 (13) | 0.65256 (10) | 0.0594 (7) | |
H44 | 0.5021 | −0.0254 | 0.6203 | 0.071* | |
C45 | 0.35197 (15) | 0.02260 (12) | 0.55730 (10) | 0.0612 (7) | |
H45A | 0.3463 | −0.0007 | 0.5918 | 0.073* | |
H45B | 0.4054 | 0.0279 | 0.5504 | 0.073* | |
O45 | 0.31817 (9) | 0.08933 (8) | 0.56087 (5) | 0.0485 (4) | |
C46 | 0.31909 (14) | −0.02038 (12) | 0.51475 (9) | 0.0528 (6) | |
C47 | 0.3461 (2) | −0.01946 (16) | 0.46359 (12) | 0.0887 (10) | |
H47 | 0.3862 | 0.0094 | 0.4550 | 0.106* | |
C48 | 0.3153 (3) | −0.0601 (2) | 0.42455 (13) | 0.1067 (13) | |
H48 | 0.3338 | −0.0585 | 0.3893 | 0.128* | |
C49 | 0.2583 (2) | −0.10262 (18) | 0.43704 (14) | 0.0928 (11) | |
H49 | 0.2378 | −0.1309 | 0.4104 | 0.111* | |
C50 | 0.23087 (17) | −0.10472 (14) | 0.48683 (13) | 0.0767 (9) | |
H50 | 0.1911 | −0.1341 | 0.4953 | 0.092* | |
C51 | 0.26147 (15) | −0.06351 (13) | 0.52530 (10) | 0.0621 (7) | |
H51 | 0.2420 | −0.0651 | 0.5602 | 0.075* | |
C52 | 0.09104 (14) | 0.03615 (12) | 0.53682 (8) | 0.0543 (7) | |
H52A | 0.1183 | 0.0023 | 0.5156 | 0.065* | |
H52B | 0.0717 | 0.0710 | 0.5124 | 0.065* | |
O52 | 0.14037 (8) | 0.06708 (7) | 0.57492 (5) | 0.0463 (4) | |
C53 | 0.02796 (12) | 0.00261 (12) | 0.56532 (8) | 0.0441 (6) | |
C54 | 0.03062 (14) | −0.06576 (13) | 0.57469 (10) | 0.0610 (7) | |
H54 | 0.0729 | −0.0904 | 0.5637 | 0.073* | |
C55 | −0.02570 (18) | −0.09923 (17) | 0.59937 (13) | 0.0856 (10) | |
H55 | −0.0236 | −0.1468 | 0.6041 | 0.103* | |
C56 | −0.08439 (18) | −0.0637 (2) | 0.61691 (11) | 0.0821 (10) | |
H56 | −0.1230 | −0.0867 | 0.6348 | 0.099* | |
C57 | −0.09000 (17) | 0.0051 (2) | 0.60969 (12) | 0.0844 (10) | |
H57 | −0.1314 | 0.0295 | 0.6227 | 0.101* | |
C58 | −0.03214 (16) | 0.03838 (15) | 0.58225 (11) | 0.0678 (8) | |
H58 | −0.0351 | 0.0855 | 0.5757 | 0.081* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0427 (13) | 0.0409 (13) | 0.0376 (11) | −0.0092 (10) | 0.0012 (10) | 0.0047 (10) |
C2 | 0.0468 (14) | 0.0356 (12) | 0.0326 (11) | −0.0011 (10) | −0.0007 (9) | 0.0010 (9) |
C3 | 0.0455 (13) | 0.0346 (12) | 0.0342 (11) | 0.0007 (10) | −0.0026 (9) | 0.0017 (9) |
C4 | 0.0454 (14) | 0.0388 (13) | 0.0332 (11) | −0.0035 (10) | −0.0020 (9) | 0.0023 (9) |
C5 | 0.0447 (14) | 0.0357 (12) | 0.0374 (11) | −0.0060 (10) | 0.0069 (10) | 0.0039 (10) |
C6 | 0.0355 (12) | 0.0433 (14) | 0.0467 (12) | −0.0050 (10) | 0.0036 (10) | 0.0104 (10) |
C7 | 0.0484 (14) | 0.0489 (14) | 0.0336 (11) | 0.0085 (11) | −0.0082 (10) | −0.0078 (10) |
C8 | 0.0341 (12) | 0.0427 (13) | 0.0414 (11) | 0.0019 (10) | −0.0097 (9) | −0.0084 (10) |
C9 | 0.0359 (12) | 0.0361 (13) | 0.0405 (12) | −0.0004 (10) | −0.0108 (9) | −0.0075 (10) |
C10 | 0.0325 (12) | 0.0423 (13) | 0.0438 (12) | −0.0041 (10) | −0.0085 (9) | −0.0046 (10) |
C11 | 0.0431 (14) | 0.0426 (14) | 0.0564 (14) | −0.0029 (11) | −0.0031 (11) | 0.0024 (11) |
C12 | 0.0554 (16) | 0.0366 (14) | 0.0683 (16) | 0.0011 (11) | −0.0027 (13) | −0.0050 (12) |
C13 | 0.0485 (14) | 0.0425 (15) | 0.0531 (14) | 0.0031 (11) | −0.0033 (11) | −0.0132 (11) |
C14 | 0.0391 (13) | 0.0484 (14) | 0.0494 (13) | −0.0022 (11) | −0.0016 (10) | −0.0041 (11) |
C15 | 0.0402 (13) | 0.0412 (13) | 0.0391 (11) | −0.0024 (10) | 0.0003 (9) | −0.0041 (10) |
C16 | 0.0476 (14) | 0.0369 (12) | 0.0324 (11) | −0.0067 (10) | 0.0031 (9) | −0.0010 (9) |
C17 | 0.0465 (13) | 0.0401 (13) | 0.0325 (11) | −0.0096 (10) | −0.0005 (9) | −0.0019 (10) |
C18 | 0.0477 (14) | 0.0446 (14) | 0.0376 (11) | −0.0010 (11) | 0.0022 (10) | 0.0012 (10) |
C19 | 0.0455 (14) | 0.0392 (13) | 0.0418 (12) | −0.0005 (11) | 0.0118 (10) | 0.0021 (10) |
C20 | 0.0395 (13) | 0.0413 (13) | 0.0488 (13) | −0.0028 (10) | 0.0094 (10) | −0.0055 (11) |
C21 | 0.0462 (14) | 0.0505 (14) | 0.0387 (11) | −0.0141 (11) | −0.0076 (10) | 0.0048 (10) |
C22 | 0.0370 (12) | 0.0475 (14) | 0.0402 (12) | −0.0101 (11) | −0.0085 (9) | 0.0085 (10) |
C23 | 0.0342 (12) | 0.0442 (14) | 0.0391 (12) | −0.0092 (10) | −0.0114 (9) | 0.0082 (10) |
C24 | 0.0314 (12) | 0.0527 (15) | 0.0428 (12) | −0.0076 (10) | −0.0062 (9) | 0.0093 (11) |
C25 | 0.0427 (14) | 0.0548 (17) | 0.0579 (15) | 0.0001 (12) | 0.0044 (11) | 0.0022 (12) |
C26 | 0.0561 (16) | 0.0431 (15) | 0.0742 (17) | 0.0024 (12) | 0.0064 (13) | 0.0125 (13) |
C27 | 0.0510 (15) | 0.0533 (16) | 0.0522 (14) | −0.0060 (12) | 0.0042 (12) | 0.0144 (12) |
C28 | 0.0371 (13) | 0.0570 (15) | 0.0420 (12) | −0.0086 (11) | −0.0047 (10) | 0.0075 (11) |
C29 | 0.0504 (15) | 0.0503 (15) | 0.0527 (14) | −0.0043 (12) | 0.0106 (12) | −0.0001 (12) |
O29 | 0.0767 (13) | 0.0675 (13) | 0.0541 (10) | 0.0026 (10) | 0.0094 (9) | −0.0126 (9) |
C30 | 0.0499 (16) | 0.0524 (16) | 0.0647 (16) | 0.0034 (12) | 0.0155 (13) | 0.0101 (13) |
O30 | 0.0742 (13) | 0.0812 (14) | 0.0728 (12) | 0.0039 (11) | 0.0104 (10) | 0.0313 (11) |
C31 | 0.098 (2) | 0.0419 (15) | 0.0528 (14) | 0.0060 (14) | −0.0262 (14) | −0.0112 (12) |
O31 | 0.0619 (11) | 0.0455 (10) | 0.0385 (8) | 0.0051 (8) | −0.0078 (7) | −0.0062 (7) |
C32 | 0.0517 (15) | 0.0403 (13) | 0.0441 (13) | 0.0025 (11) | −0.0098 (11) | −0.0032 (10) |
C33 | 0.0511 (16) | 0.0608 (17) | 0.0688 (17) | 0.0099 (13) | −0.0010 (13) | −0.0002 (14) |
C34 | 0.077 (2) | 0.0676 (19) | 0.0611 (17) | −0.0085 (17) | −0.0007 (15) | 0.0074 (15) |
C35 | 0.069 (2) | 0.0555 (18) | 0.079 (2) | −0.0095 (15) | −0.0217 (16) | 0.0170 (15) |
C36 | 0.0649 (19) | 0.0579 (19) | 0.113 (2) | 0.0219 (15) | −0.0036 (18) | 0.0170 (18) |
C37 | 0.076 (2) | 0.0588 (18) | 0.0695 (17) | 0.0138 (15) | 0.0177 (14) | 0.0009 (14) |
C38 | 0.0404 (13) | 0.0485 (14) | 0.0523 (13) | 0.0069 (11) | −0.0121 (10) | −0.0097 (11) |
O38 | 0.0387 (8) | 0.0376 (9) | 0.0416 (8) | 0.0044 (7) | −0.0104 (6) | −0.0073 (6) |
C39 | 0.0383 (13) | 0.0433 (14) | 0.0481 (13) | 0.0053 (10) | −0.0085 (10) | −0.0049 (11) |
C40 | 0.0536 (16) | 0.0610 (17) | 0.0563 (15) | 0.0056 (13) | 0.0009 (12) | 0.0053 (13) |
C41 | 0.076 (2) | 0.064 (2) | 0.088 (2) | 0.0033 (16) | −0.0081 (17) | 0.0254 (18) |
C42 | 0.068 (2) | 0.0484 (17) | 0.116 (3) | 0.0100 (15) | −0.0113 (18) | 0.0000 (19) |
C43 | 0.084 (2) | 0.0627 (19) | 0.0746 (19) | 0.0194 (16) | −0.0066 (16) | −0.0204 (16) |
C44 | 0.0737 (19) | 0.0489 (16) | 0.0554 (15) | 0.0175 (13) | −0.0102 (13) | −0.0045 (12) |
C45 | 0.0768 (19) | 0.0448 (15) | 0.0620 (15) | −0.0121 (14) | −0.0210 (14) | 0.0084 (12) |
O45 | 0.0616 (10) | 0.0441 (10) | 0.0398 (8) | −0.0140 (8) | −0.0063 (7) | 0.0066 (7) |
C46 | 0.0667 (17) | 0.0404 (14) | 0.0513 (14) | −0.0019 (13) | −0.0131 (12) | 0.0061 (11) |
C47 | 0.121 (3) | 0.075 (2) | 0.071 (2) | −0.011 (2) | 0.0152 (18) | −0.0011 (17) |
C48 | 0.173 (4) | 0.093 (3) | 0.0547 (19) | 0.011 (3) | 0.009 (2) | −0.0170 (19) |
C49 | 0.123 (3) | 0.077 (2) | 0.079 (2) | 0.015 (2) | −0.028 (2) | −0.0315 (19) |
C50 | 0.076 (2) | 0.067 (2) | 0.087 (2) | −0.0019 (16) | −0.0095 (17) | −0.0323 (17) |
C51 | 0.0699 (19) | 0.0556 (17) | 0.0608 (16) | −0.0034 (14) | −0.0054 (13) | −0.0121 (13) |
C52 | 0.0632 (17) | 0.0603 (16) | 0.0393 (12) | −0.0296 (13) | −0.0124 (11) | 0.0039 (11) |
O52 | 0.0549 (10) | 0.0454 (10) | 0.0387 (8) | −0.0202 (8) | −0.0161 (7) | 0.0043 (7) |
C53 | 0.0455 (14) | 0.0502 (15) | 0.0368 (11) | −0.0123 (12) | −0.0136 (10) | 0.0008 (10) |
C54 | 0.0506 (16) | 0.0590 (17) | 0.0735 (17) | −0.0101 (13) | −0.0084 (13) | 0.0212 (14) |
C55 | 0.071 (2) | 0.085 (2) | 0.100 (2) | −0.0185 (19) | −0.0090 (19) | 0.0452 (19) |
C56 | 0.060 (2) | 0.130 (3) | 0.0564 (17) | −0.025 (2) | −0.0014 (14) | 0.015 (2) |
C57 | 0.0464 (18) | 0.138 (3) | 0.0686 (19) | 0.008 (2) | −0.0082 (14) | −0.042 (2) |
C58 | 0.0595 (19) | 0.0681 (19) | 0.0759 (18) | −0.0007 (15) | −0.0199 (15) | −0.0220 (15) |
C1—C6 | 1.384 (3) | C31—O31 | 1.457 (3) |
C1—C2 | 1.398 (3) | C31—C32 | 1.490 (3) |
C1—C28 | 1.517 (3) | C31—H31A | 0.9900 |
C2—O31 | 1.371 (2) | C31—H31B | 0.9900 |
C2—C3 | 1.410 (3) | C32—C37 | 1.372 (3) |
C3—C4 | 1.383 (3) | C32—C33 | 1.381 (3) |
C3—C7 | 1.509 (3) | C33—C34 | 1.379 (4) |
C4—C5 | 1.397 (3) | C33—H33 | 0.9500 |
C4—H4 | 0.9500 | C34—C35 | 1.357 (4) |
C5—C6 | 1.388 (3) | C34—H34 | 0.9500 |
C5—C29 | 1.465 (3) | C35—C36 | 1.347 (4) |
C6—H6 | 0.9500 | C35—H35 | 0.9500 |
C7—C8 | 1.523 (3) | C36—C37 | 1.390 (4) |
C7—H7A | 0.9900 | C36—H36 | 0.9500 |
C7—H7B | 0.9900 | C37—H37 | 0.9500 |
C8—C13 | 1.393 (3) | C38—O38 | 1.434 (2) |
C8—C9 | 1.403 (3) | C38—C39 | 1.493 (3) |
C9—C10 | 1.394 (3) | C38—H38A | 0.9900 |
C9—O38 | 1.396 (2) | C38—H38B | 0.9900 |
C10—C11 | 1.395 (3) | C39—C44 | 1.370 (3) |
C10—C14 | 1.519 (3) | C39—C40 | 1.384 (3) |
C11—C12 | 1.376 (3) | C40—C41 | 1.369 (4) |
C11—H11 | 0.9500 | C40—H40 | 0.9500 |
C12—C13 | 1.373 (3) | C41—C42 | 1.360 (4) |
C12—H12 | 0.9500 | C41—H41 | 0.9500 |
C13—H13 | 0.9500 | C42—C43 | 1.376 (4) |
C14—C15 | 1.515 (3) | C42—H42 | 0.9500 |
C14—H14A | 0.9900 | C43—C44 | 1.385 (3) |
C14—H14B | 0.9900 | C43—H43 | 0.9500 |
C15—C20 | 1.394 (3) | C44—H44 | 0.9500 |
C15—C16 | 1.395 (3) | C45—O45 | 1.460 (3) |
C16—O45 | 1.378 (2) | C45—C46 | 1.495 (3) |
C16—C17 | 1.406 (3) | C45—H45A | 0.9900 |
C17—C18 | 1.385 (3) | C45—H45B | 0.9900 |
C17—C21 | 1.509 (3) | C46—C51 | 1.375 (3) |
C18—C19 | 1.389 (3) | C46—C47 | 1.381 (4) |
C18—H18 | 0.9500 | C47—C48 | 1.389 (5) |
C19—C20 | 1.385 (3) | C47—H47 | 0.9500 |
C19—C30 | 1.461 (3) | C48—C49 | 1.370 (5) |
C20—H20 | 0.9500 | C48—H48 | 0.9500 |
C21—C22 | 1.517 (3) | C49—C50 | 1.352 (4) |
C21—H21A | 0.9900 | C49—H49 | 0.9500 |
C21—H21B | 0.9900 | C50—C51 | 1.385 (3) |
C22—C27 | 1.381 (3) | C50—H50 | 0.9500 |
C22—C23 | 1.408 (3) | C51—H51 | 0.9500 |
C23—O52 | 1.380 (2) | C52—O52 | 1.449 (2) |
C23—C24 | 1.399 (3) | C52—C53 | 1.505 (3) |
C24—C25 | 1.383 (3) | C52—H52A | 0.9900 |
C24—C28 | 1.529 (3) | C52—H52B | 0.9900 |
C25—C26 | 1.387 (3) | C53—C58 | 1.368 (3) |
C25—H25 | 0.9500 | C53—C54 | 1.376 (3) |
C26—C27 | 1.378 (3) | C54—C55 | 1.367 (4) |
C26—H26 | 0.9500 | C54—H54 | 0.9500 |
C27—H27 | 0.9500 | C55—C56 | 1.350 (4) |
C28—H28A | 0.9900 | C55—H55 | 0.9500 |
C28—H28B | 0.9900 | C56—C57 | 1.378 (5) |
C29—O29 | 1.207 (3) | C56—H56 | 0.9500 |
C29—H29 | 0.9500 | C57—C58 | 1.419 (4) |
C30—O30 | 1.205 (3) | C57—H57 | 0.9500 |
C30—H30 | 0.9500 | C58—H58 | 0.9500 |
C6—C1—C2 | 117.28 (19) | C19—C30—H30 | 116.9 |
C6—C1—C28 | 121.1 (2) | O31—C31—C32 | 115.26 (19) |
C2—C1—C28 | 121.42 (19) | O31—C31—H31A | 108.5 |
O31—C2—C1 | 120.77 (18) | C32—C31—H31A | 108.5 |
O31—C2—C3 | 116.96 (19) | O31—C31—H31B | 108.5 |
C1—C2—C3 | 121.98 (19) | C32—C31—H31B | 108.5 |
C4—C3—C2 | 118.1 (2) | H31A—C31—H31B | 107.5 |
C4—C3—C7 | 122.58 (18) | C2—O31—C31 | 115.93 (18) |
C2—C3—C7 | 118.97 (18) | C37—C32—C33 | 117.3 (2) |
C3—C4—C5 | 120.86 (19) | C37—C32—C31 | 121.9 (2) |
C3—C4—H4 | 119.6 | C33—C32—C31 | 120.7 (2) |
C5—C4—H4 | 119.6 | C34—C33—C32 | 121.3 (2) |
C6—C5—C4 | 119.11 (19) | C34—C33—H33 | 119.4 |
C6—C5—C29 | 119.6 (2) | C32—C33—H33 | 119.4 |
C4—C5—C29 | 121.3 (2) | C35—C34—C33 | 120.1 (3) |
C1—C6—C5 | 122.2 (2) | C35—C34—H34 | 119.9 |
C1—C6—H6 | 118.9 | C33—C34—H34 | 119.9 |
C5—C6—H6 | 118.9 | C36—C35—C34 | 119.8 (3) |
C3—C7—C8 | 109.23 (17) | C36—C35—H35 | 120.1 |
C3—C7—H7A | 109.8 | C34—C35—H35 | 120.1 |
C8—C7—H7A | 109.8 | C35—C36—C37 | 120.5 (3) |
C3—C7—H7B | 109.8 | C35—C36—H36 | 119.8 |
C8—C7—H7B | 109.8 | C37—C36—H36 | 119.7 |
H7A—C7—H7B | 108.3 | C32—C37—C36 | 120.9 (3) |
C13—C8—C9 | 117.7 (2) | C32—C37—H37 | 119.6 |
C13—C8—C7 | 120.14 (19) | C36—C37—H37 | 119.6 |
C9—C8—C7 | 121.97 (19) | O38—C38—C39 | 109.80 (17) |
C10—C9—O38 | 119.02 (18) | O38—C38—H38A | 109.7 |
C10—C9—C8 | 122.0 (2) | C39—C38—H38A | 109.7 |
O38—C9—C8 | 118.99 (18) | O38—C38—H38B | 109.7 |
C9—C10—C11 | 117.6 (2) | C39—C38—H38B | 109.7 |
C9—C10—C14 | 122.55 (19) | H38A—C38—H38B | 108.2 |
C11—C10—C14 | 119.7 (2) | C9—O38—C38 | 111.93 (15) |
C12—C11—C10 | 121.4 (2) | C44—C39—C40 | 118.1 (2) |
C12—C11—H11 | 119.3 | C44—C39—C38 | 121.0 (2) |
C10—C11—H11 | 119.3 | C40—C39—C38 | 120.9 (2) |
C13—C12—C11 | 120.0 (2) | C41—C40—C39 | 121.0 (3) |
C13—C12—H12 | 120.0 | C41—C40—H40 | 119.5 |
C11—C12—H12 | 120.0 | C39—C40—H40 | 119.5 |
C12—C13—C8 | 121.3 (2) | C42—C41—C40 | 120.5 (3) |
C12—C13—H13 | 119.4 | C42—C41—H41 | 119.8 |
C8—C13—H13 | 119.4 | C40—C41—H41 | 119.8 |
C15—C14—C10 | 109.78 (17) | C41—C42—C43 | 119.6 (3) |
C15—C14—H14A | 109.7 | C41—C42—H42 | 120.2 |
C10—C14—H14A | 109.7 | C43—C42—H42 | 120.2 |
C15—C14—H14B | 109.7 | C42—C43—C44 | 119.7 (3) |
C10—C14—H14B | 109.7 | C42—C43—H43 | 120.1 |
H14A—C14—H14B | 108.2 | C44—C43—H43 | 120.1 |
C20—C15—C16 | 117.12 (19) | C39—C44—C43 | 121.0 (2) |
C20—C15—C14 | 121.15 (19) | C39—C44—H44 | 119.5 |
C16—C15—C14 | 121.23 (19) | C43—C44—H44 | 119.5 |
O45—C16—C15 | 119.72 (18) | O45—C45—C46 | 113.15 (19) |
O45—C16—C17 | 117.48 (18) | O45—C45—H45A | 108.9 |
C15—C16—C17 | 122.60 (19) | C46—C45—H45A | 108.9 |
C18—C17—C16 | 117.5 (2) | O45—C45—H45B | 108.9 |
C18—C17—C21 | 122.30 (19) | C46—C45—H45B | 108.9 |
C16—C17—C21 | 119.96 (18) | H45A—C45—H45B | 107.8 |
C17—C18—C19 | 121.2 (2) | C16—O45—C45 | 115.29 (18) |
C17—C18—H18 | 119.4 | C51—C46—C47 | 117.3 (2) |
C19—C18—H18 | 119.4 | C51—C46—C45 | 121.2 (2) |
C20—C19—C18 | 119.56 (19) | C47—C46—C45 | 121.5 (3) |
C20—C19—C30 | 118.7 (2) | C46—C47—C48 | 120.9 (3) |
C18—C19—C30 | 121.7 (2) | C46—C47—H47 | 119.6 |
C19—C20—C15 | 121.6 (2) | C48—C47—H47 | 119.6 |
C19—C20—H20 | 119.2 | C49—C48—C47 | 119.7 (3) |
C15—C20—H20 | 119.2 | C49—C48—H48 | 120.1 |
C17—C21—C22 | 110.21 (17) | C47—C48—H48 | 120.1 |
C17—C21—H21A | 109.6 | C50—C49—C48 | 120.7 (3) |
C22—C21—H21A | 109.6 | C50—C49—H49 | 119.7 |
C17—C21—H21B | 109.6 | C48—C49—H49 | 119.7 |
C22—C21—H21B | 109.6 | C49—C50—C51 | 119.1 (3) |
H21A—C21—H21B | 108.1 | C49—C50—H50 | 120.5 |
C27—C22—C23 | 117.7 (2) | C51—C50—H50 | 120.5 |
C27—C22—C21 | 120.04 (19) | C46—C51—C50 | 122.3 (3) |
C23—C22—C21 | 122.1 (2) | C46—C51—H51 | 118.8 |
O52—C23—C24 | 118.60 (18) | C50—C51—H51 | 118.8 |
O52—C23—C22 | 120.0 (2) | O52—C52—C53 | 109.76 (16) |
C24—C23—C22 | 121.4 (2) | O52—C52—H52A | 109.7 |
C25—C24—C23 | 118.2 (2) | C53—C52—H52A | 109.7 |
C25—C24—C28 | 119.5 (2) | O52—C52—H52B | 109.7 |
C23—C24—C28 | 122.3 (2) | C53—C52—H52B | 109.7 |
C24—C25—C26 | 121.4 (2) | H52A—C52—H52B | 108.2 |
C24—C25—H25 | 119.3 | C23—O52—C52 | 115.91 (16) |
C26—C25—H25 | 119.3 | C58—C53—C54 | 119.0 (2) |
C27—C26—C25 | 119.1 (2) | C58—C53—C52 | 121.7 (2) |
C27—C26—H26 | 120.5 | C54—C53—C52 | 119.4 (2) |
C25—C26—H26 | 120.5 | C55—C54—C53 | 122.0 (3) |
C26—C27—C22 | 122.1 (2) | C55—C54—H54 | 119.0 |
C26—C27—H27 | 119.0 | C53—C54—H54 | 119.0 |
C22—C27—H27 | 119.0 | C56—C55—C54 | 118.9 (3) |
C1—C28—C24 | 111.34 (17) | C56—C55—H55 | 120.5 |
C1—C28—H28A | 109.4 | C54—C55—H55 | 120.5 |
C24—C28—H28A | 109.4 | C55—C56—C57 | 122.1 (3) |
C1—C28—H28B | 109.4 | C55—C56—H56 | 119.0 |
C24—C28—H28B | 109.4 | C57—C56—H56 | 119.0 |
H28A—C28—H28B | 108.0 | C56—C57—C58 | 118.0 (3) |
O29—C29—C5 | 126.1 (2) | C56—C57—H57 | 121.0 |
O29—C29—H29 | 117.0 | C58—C57—H57 | 121.0 |
C5—C29—H29 | 117.0 | C53—C58—C57 | 120.0 (3) |
O30—C30—C19 | 126.2 (2) | C53—C58—H58 | 120.0 |
O30—C30—H30 | 116.9 | C57—C58—H58 | 120.0 |