Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680501336X/bt6661sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680501336X/bt6661Isup2.hkl |
CCDC reference: 274342
Data collection: COLLECT (Nonius, 1998); cell refinement: DENZO aand SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1991); software used to prepare material for publication: SHELXL97, PARST95 (Nardelli, 1995) and PLATON (Spek, 2001).
C20H19F3N2O4 | F(000) = 1696 |
Mr = 408.37 | Dx = 1.414 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 27239 reflections |
a = 22.4800 (14) Å | θ = 2.9–25.4° |
b = 22.1594 (15) Å | µ = 0.12 mm−1 |
c = 7.7029 (6) Å | T = 173 K |
V = 3837.1 (5) Å3 | Needle, colourless |
Z = 8 | 0.34 × 0.12 × 0.10 mm |
Nonius KappaCCD diffractometer | 2109 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
Graphite monochromator | θmax = 25.4°, θmin = 2.9° |
Detector resolution: 19 vertical, 18 horizontal pixels mm-1 | h = −27→27 |
345 frames via ω–rotation (Δω=1°) and two times 100 s per frame (three sets at different κ–angles) scans | k = −26→26 |
27239 measured reflections | l = −9→9 |
3790 independent reflections |
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)] = 0.033 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.050 | H-atom parameters constrained |
S = 0.86 | w = 1/[σ2(Fo2) + (0.005P)2] where P = (Fo2 + 2Fc2)/3 |
3790 reflections | (Δ/σ)max < 0.001 |
529 parameters | Δρmax = 0.14 e Å−3 |
1 restraint | Δρmin = −0.15 e Å−3 |
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 | ||
F1 | −0.18781 (8) | 0.90406 (10) | 0.4276 (3) | 0.0715 (8) | |
F2 | −0.17031 (9) | 0.98851 (10) | 0.5498 (3) | 0.0642 (7) | |
F3 | −0.21423 (8) | 0.98733 (9) | 0.3055 (3) | 0.0667 (7) | |
F1' | −0.20367 (8) | 0.42721 (9) | 0.5017 (3) | 0.0516 (6) | |
F2' | −0.18927 (8) | 0.51707 (9) | 0.5927 (3) | 0.0595 (6) | |
F3' | −0.23558 (8) | 0.50282 (9) | 0.3552 (3) | 0.0630 (6) | |
O1 | 0.12410 (10) | 0.83558 (10) | 0.7091 (3) | 0.0487 (7) | |
O2 | 0.20169 (10) | 0.80158 (10) | 0.5492 (3) | 0.0409 (7) | |
O3 | 0.18089 (10) | 0.75591 (9) | 0.9671 (3) | 0.0428 (6) | |
O4 | 0.05707 (9) | 0.78453 (9) | 0.3639 (3) | 0.0345 (6) | |
O1' | 0.09532 (10) | 0.30972 (10) | 0.8162 (3) | 0.0485 (7) | |
O2' | 0.16562 (10) | 0.23889 (10) | 0.8601 (3) | 0.0487 (7) | |
O3' | 0.20030 (9) | 0.34752 (10) | 0.5919 (3) | 0.0399 (6) | |
O4' | 0.03553 (9) | 0.30183 (9) | 0.3520 (3) | 0.0341 (6) | |
N1 | 0.16091 (11) | 0.70979 (12) | 0.8582 (4) | 0.0350 (7) | |
N2 | 0.01372 (11) | 0.83046 (12) | 0.3573 (4) | 0.0316 (7) | |
N1' | 0.17878 (12) | 0.30054 (12) | 0.4869 (3) | 0.0338 (7) | |
N2' | −0.00869 (11) | 0.34702 (12) | 0.3618 (4) | 0.0329 (7) | |
C1 | 0.13219 (14) | 0.68363 (14) | 0.5719 (4) | 0.0272 (9) | |
C2 | 0.07979 (14) | 0.68811 (14) | 0.4757 (4) | 0.0285 (9) | |
C3 | 0.06578 (14) | 0.64182 (15) | 0.3611 (4) | 0.0338 (9) | |
H3A | 0.0309 | 0.6440 | 0.2964 | 0.041* | |
C4 | 0.10272 (16) | 0.59270 (15) | 0.3418 (5) | 0.0385 (9) | |
H4A | 0.0923 | 0.5618 | 0.2660 | 0.046* | |
C5 | 0.15467 (15) | 0.58919 (15) | 0.4337 (4) | 0.0369 (10) | |
H5A | 0.1800 | 0.5565 | 0.4180 | 0.044* | |
C6 | 0.16950 (14) | 0.63431 (14) | 0.5497 (4) | 0.0342 (9) | |
H6A | 0.2046 | 0.6316 | 0.6132 | 0.041* | |
C7 | 0.14879 (14) | 0.72980 (15) | 0.7044 (5) | 0.0288 (9) | |
C8 | 0.15537 (17) | 0.79495 (17) | 0.6573 (5) | 0.0368 (10) | |
C9 | 0.21402 (16) | 0.86298 (14) | 0.4952 (5) | 0.0575 (11) | |
H9A | 0.2455 | 0.8629 | 0.4108 | 0.086* | |
H9B | 0.2259 | 0.8864 | 0.5941 | 0.086* | |
H9C | 0.1789 | 0.8803 | 0.4448 | 0.086* | |
C10 | 0.18715 (15) | 0.73239 (14) | 1.1403 (4) | 0.0451 (10) | |
H10A | 0.2072 | 0.7615 | 1.2117 | 0.068* | |
H10B | 0.2099 | 0.6958 | 1.1370 | 0.068* | |
H10C | 0.1485 | 0.7242 | 1.1878 | 0.068* | |
C11 | −0.01594 (15) | 0.92220 (15) | 0.2350 (4) | 0.0270 (9) | |
C12 | −0.07177 (15) | 0.91759 (14) | 0.3129 (4) | 0.0317 (9) | |
H12B | −0.0823 | 0.8824 | 0.3710 | 0.038* | |
C13 | −0.11141 (14) | 0.96477 (15) | 0.3043 (4) | 0.0291 (9) | |
C14 | −0.09735 (16) | 1.01821 (14) | 0.2189 (4) | 0.0326 (9) | |
H14A | −0.1242 | 1.0501 | 0.2158 | 0.039* | |
C15 | −0.04321 (16) | 1.02258 (14) | 0.1399 (4) | 0.0363 (10) | |
H15A | −0.0332 | 1.0578 | 0.0813 | 0.044* | |
C16 | −0.00283 (15) | 0.97523 (15) | 0.1455 (4) | 0.0351 (10) | |
H16A | 0.0335 | 0.9789 | 0.0888 | 0.042* | |
C17 | −0.17075 (17) | 0.96017 (18) | 0.3931 (6) | 0.0487 (11) | |
C18 | 0.02781 (14) | 0.87207 (15) | 0.2486 (4) | 0.0294 (9) | |
C19 | 0.08335 (14) | 0.87402 (13) | 0.1415 (5) | 0.0464 (11) | |
H19A | 0.1031 | 0.8357 | 0.1476 | 0.070* | |
H19B | 0.1092 | 0.9050 | 0.1851 | 0.070* | |
H19C | 0.0733 | 0.8827 | 0.0229 | 0.070* | |
C20 | 0.03815 (13) | 0.74053 (13) | 0.4909 (4) | 0.0322 (9) | |
H20A | −0.0024 | 0.7278 | 0.4679 | 0.039* | |
H20B | 0.0399 | 0.7576 | 0.6067 | 0.039* | |
C1' | 0.12275 (15) | 0.20897 (15) | 0.4869 (4) | 0.0291 (9) | |
C2' | 0.06367 (15) | 0.20352 (15) | 0.4372 (4) | 0.0299 (9) | |
C3' | 0.04655 (15) | 0.15144 (15) | 0.3500 (4) | 0.0359 (9) | |
H3'A | 0.0076 | 0.1478 | 0.3105 | 0.043* | |
C4' | 0.08644 (17) | 0.10490 (15) | 0.3209 (5) | 0.0395 (10) | |
H4'A | 0.0738 | 0.0699 | 0.2654 | 0.047* | |
C5' | 0.14457 (16) | 0.11018 (15) | 0.3735 (4) | 0.0396 (10) | |
H5'A | 0.1713 | 0.0789 | 0.3546 | 0.048* | |
C6' | 0.16287 (15) | 0.16279 (15) | 0.4554 (4) | 0.0375 (9) | |
H6'A | 0.2024 | 0.1671 | 0.4893 | 0.045* | |
C7' | 0.14574 (15) | 0.26473 (15) | 0.5734 (4) | 0.0312 (9) | |
C8' | 0.13245 (17) | 0.27473 (17) | 0.7622 (5) | 0.0383 (10) | |
C9' | 0.15676 (16) | 0.24265 (16) | 1.0492 (4) | 0.0605 (12) | |
H9'A | 0.1827 | 0.2145 | 1.1062 | 0.091* | |
H9'B | 0.1162 | 0.2331 | 1.0766 | 0.091* | |
H9'C | 0.1656 | 0.2828 | 1.0881 | 0.091* | |
C10' | 0.23487 (15) | 0.38762 (15) | 0.4871 (5) | 0.0525 (11) | |
H10D | 0.2682 | 0.3662 | 0.4395 | 0.079* | |
H10E | 0.2489 | 0.4205 | 0.5572 | 0.079* | |
H10F | 0.2107 | 0.4030 | 0.3944 | 0.079* | |
C11' | −0.03794 (15) | 0.44339 (15) | 0.2684 (4) | 0.0285 (9) | |
C12' | −0.09212 (14) | 0.43903 (13) | 0.3560 (4) | 0.0286 (8) | |
H12' | −0.1013 | 0.4038 | 0.4159 | 0.034* | |
C13' | −0.13227 (14) | 0.48613 (14) | 0.3554 (5) | 0.0284 (8) | |
C14' | −0.11938 (16) | 0.53894 (14) | 0.2642 (4) | 0.0342 (9) | |
H14' | −0.1463 | 0.5708 | 0.2631 | 0.041* | |
C15' | −0.06644 (17) | 0.54343 (15) | 0.1759 (4) | 0.0393 (10) | |
H15' | −0.0576 | 0.5786 | 0.1154 | 0.047* | |
C16' | −0.02614 (15) | 0.49607 (16) | 0.1763 (4) | 0.0350 (9) | |
H16' | 0.0092 | 0.4995 | 0.1143 | 0.042* | |
C17' | −0.18901 (16) | 0.48230 (16) | 0.4482 (5) | 0.0401 (10) | |
C18' | 0.00603 (15) | 0.39348 (15) | 0.2714 (4) | 0.0293 (9) | |
C19' | 0.06383 (15) | 0.39877 (15) | 0.1766 (5) | 0.0542 (12) | |
H19D | 0.0899 | 0.3667 | 0.2119 | 0.065* | |
H19E | 0.0819 | 0.4369 | 0.2031 | 0.065* | |
H19F | 0.0568 | 0.3961 | 0.0539 | 0.065* | |
C20' | 0.01912 (13) | 0.25281 (14) | 0.4670 (4) | 0.0356 (9) | |
H20C | −0.0207 | 0.2387 | 0.4408 | 0.043* | |
H20D | 0.0202 | 0.2660 | 0.5870 | 0.043* |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0471 (14) | 0.0444 (15) | 0.123 (2) | −0.0013 (11) | 0.0262 (13) | 0.0143 (14) |
F2 | 0.0626 (15) | 0.0748 (17) | 0.0552 (16) | 0.0096 (13) | 0.0149 (14) | 0.0017 (14) |
F3 | 0.0372 (13) | 0.0857 (18) | 0.0772 (18) | 0.0124 (11) | −0.0066 (13) | 0.0231 (14) |
F1' | 0.0457 (13) | 0.0367 (13) | 0.0726 (16) | −0.0002 (11) | 0.0133 (11) | 0.0078 (12) |
F2' | 0.0578 (15) | 0.0586 (15) | 0.0623 (16) | −0.0075 (11) | 0.0172 (13) | −0.0192 (13) |
F3' | 0.0371 (13) | 0.0787 (16) | 0.0732 (15) | 0.0044 (11) | −0.0075 (14) | 0.0281 (14) |
O1 | 0.0631 (18) | 0.0327 (17) | 0.0504 (18) | 0.0048 (14) | 0.0069 (15) | −0.0050 (14) |
O2 | 0.0522 (17) | 0.0330 (16) | 0.0374 (16) | −0.0074 (13) | 0.0125 (14) | 0.0039 (13) |
O3 | 0.0556 (17) | 0.0367 (15) | 0.0360 (15) | −0.0103 (13) | −0.0032 (14) | −0.0021 (14) |
O4 | 0.0401 (15) | 0.0283 (14) | 0.0349 (14) | 0.0086 (12) | 0.0036 (13) | 0.0065 (13) |
O1' | 0.0561 (18) | 0.0464 (18) | 0.0429 (17) | 0.0058 (13) | 0.0121 (15) | −0.0073 (14) |
O2' | 0.0654 (18) | 0.0512 (18) | 0.0295 (16) | 0.0157 (14) | 0.0038 (15) | 0.0068 (16) |
O3' | 0.0516 (16) | 0.0320 (15) | 0.0361 (16) | −0.0130 (13) | 0.0098 (14) | −0.0037 (13) |
O4' | 0.0327 (14) | 0.0302 (15) | 0.0395 (14) | 0.0037 (11) | 0.0054 (13) | 0.0070 (13) |
N1 | 0.0336 (18) | 0.0353 (19) | 0.0361 (19) | −0.0046 (14) | 0.0030 (16) | −0.0082 (18) |
N2 | 0.0381 (18) | 0.0244 (18) | 0.0322 (19) | 0.0041 (15) | −0.0011 (16) | 0.0043 (17) |
N1' | 0.042 (2) | 0.0254 (18) | 0.0334 (18) | −0.0032 (15) | 0.0021 (16) | −0.0045 (17) |
N2' | 0.0334 (18) | 0.0320 (19) | 0.0334 (18) | 0.0039 (15) | −0.0043 (16) | −0.0010 (18) |
C1 | 0.030 (2) | 0.021 (2) | 0.030 (2) | −0.0018 (18) | 0.0053 (19) | −0.0035 (19) |
C2 | 0.033 (2) | 0.027 (2) | 0.026 (2) | 0.0011 (18) | 0.0035 (19) | 0.003 (2) |
C3 | 0.036 (2) | 0.037 (2) | 0.029 (2) | −0.0022 (19) | −0.002 (2) | 0.003 (2) |
C4 | 0.051 (3) | 0.030 (2) | 0.035 (2) | −0.009 (2) | 0.005 (2) | −0.004 (2) |
C5 | 0.042 (3) | 0.032 (2) | 0.037 (2) | 0.005 (2) | 0.008 (2) | −0.003 (2) |
C6 | 0.035 (2) | 0.030 (2) | 0.037 (2) | 0.0000 (19) | 0.0004 (19) | −0.002 (2) |
C7 | 0.030 (2) | 0.028 (2) | 0.028 (2) | 0.0027 (18) | 0.0063 (18) | 0.000 (2) |
C8 | 0.045 (3) | 0.034 (3) | 0.031 (2) | 0.000 (2) | −0.007 (2) | −0.005 (2) |
C9 | 0.079 (3) | 0.040 (3) | 0.053 (3) | −0.013 (2) | 0.009 (2) | 0.006 (2) |
C10 | 0.052 (3) | 0.053 (3) | 0.030 (2) | −0.002 (2) | 0.001 (2) | 0.006 (2) |
C11 | 0.032 (2) | 0.027 (2) | 0.021 (2) | −0.0030 (18) | −0.0036 (18) | −0.0042 (18) |
C12 | 0.036 (2) | 0.028 (2) | 0.031 (2) | −0.0002 (18) | −0.002 (2) | 0.0014 (19) |
C13 | 0.025 (2) | 0.031 (2) | 0.032 (2) | −0.0007 (18) | −0.0014 (19) | −0.0051 (19) |
C14 | 0.043 (3) | 0.022 (2) | 0.033 (2) | 0.0014 (19) | −0.008 (2) | 0.0026 (19) |
C15 | 0.049 (3) | 0.025 (2) | 0.035 (2) | −0.003 (2) | −0.002 (2) | 0.007 (2) |
C16 | 0.043 (2) | 0.036 (2) | 0.026 (2) | −0.005 (2) | 0.0038 (19) | −0.002 (2) |
C17 | 0.048 (3) | 0.035 (3) | 0.063 (3) | 0.005 (2) | −0.011 (3) | 0.006 (2) |
C18 | 0.028 (2) | 0.026 (2) | 0.034 (2) | 0.0017 (18) | −0.0049 (19) | −0.0053 (19) |
C19 | 0.042 (3) | 0.043 (3) | 0.055 (3) | 0.0021 (19) | 0.006 (2) | 0.013 (2) |
C20 | 0.035 (2) | 0.029 (2) | 0.032 (2) | 0.0002 (18) | 0.0016 (18) | 0.007 (2) |
C1' | 0.033 (2) | 0.030 (2) | 0.024 (2) | 0.0005 (19) | 0.0020 (18) | −0.0025 (19) |
C2' | 0.039 (3) | 0.028 (2) | 0.022 (2) | −0.0021 (19) | 0.0056 (18) | 0.0020 (18) |
C3' | 0.032 (2) | 0.043 (3) | 0.033 (2) | −0.003 (2) | 0.002 (2) | 0.001 (2) |
C4' | 0.050 (3) | 0.034 (2) | 0.034 (2) | −0.007 (2) | 0.004 (2) | −0.0105 (19) |
C5' | 0.048 (3) | 0.032 (2) | 0.038 (2) | 0.0080 (19) | 0.003 (2) | −0.012 (2) |
C6' | 0.034 (2) | 0.037 (2) | 0.041 (2) | 0.001 (2) | −0.001 (2) | −0.003 (2) |
C7' | 0.033 (2) | 0.032 (2) | 0.029 (2) | 0.0065 (19) | 0.0022 (19) | −0.005 (2) |
C8' | 0.042 (3) | 0.033 (3) | 0.040 (3) | −0.006 (2) | 0.008 (2) | −0.001 (2) |
C9' | 0.076 (3) | 0.078 (3) | 0.027 (2) | 0.007 (3) | 0.008 (2) | 0.007 (2) |
C10' | 0.062 (3) | 0.041 (3) | 0.054 (3) | −0.015 (2) | 0.015 (2) | −0.002 (2) |
C11' | 0.032 (2) | 0.028 (2) | 0.025 (2) | −0.0033 (19) | −0.0044 (19) | −0.0022 (19) |
C12' | 0.038 (2) | 0.025 (2) | 0.022 (2) | −0.0036 (18) | −0.006 (2) | 0.0006 (19) |
C13' | 0.034 (2) | 0.022 (2) | 0.029 (2) | −0.0017 (18) | −0.005 (2) | 0.000 (2) |
C14' | 0.044 (3) | 0.026 (2) | 0.033 (2) | −0.0015 (19) | −0.005 (2) | −0.0001 (19) |
C15' | 0.055 (3) | 0.029 (2) | 0.034 (2) | −0.009 (2) | 0.001 (2) | 0.0047 (19) |
C16' | 0.041 (2) | 0.034 (2) | 0.030 (2) | −0.004 (2) | 0.0013 (18) | 0.000 (2) |
C17' | 0.039 (3) | 0.027 (2) | 0.054 (3) | 0.001 (2) | −0.006 (2) | 0.002 (2) |
C18' | 0.033 (2) | 0.031 (2) | 0.024 (2) | −0.0054 (19) | −0.0022 (18) | −0.004 (2) |
C19' | 0.053 (3) | 0.039 (2) | 0.071 (3) | 0.005 (2) | 0.020 (2) | 0.006 (2) |
C20' | 0.035 (2) | 0.037 (2) | 0.036 (2) | 0.0008 (19) | 0.002 (2) | 0.004 (2) |
F1—C17 | 1.328 (4) | C13—C17 | 1.502 (5) |
F2—C17 | 1.361 (4) | C14—C15 | 1.364 (4) |
F3—C17 | 1.331 (4) | C14—H14A | 0.9300 |
F1'—C17' | 1.330 (3) | C15—C16 | 1.388 (4) |
F2'—C17' | 1.354 (4) | C15—H15A | 0.9300 |
F3'—C17' | 1.347 (4) | C16—H16A | 0.9300 |
O1—C8 | 1.210 (4) | C18—C19 | 1.497 (4) |
O2—C8 | 1.341 (4) | C19—H19A | 0.9600 |
O2—C9 | 1.450 (3) | C19—H19B | 0.9600 |
O3—N1 | 1.396 (3) | C19—H19C | 0.9600 |
O3—C10 | 1.439 (3) | C20—H20A | 0.9700 |
O4—N2 | 1.410 (3) | C20—H20B | 0.9700 |
O4—C20 | 1.445 (3) | C1'—C6' | 1.386 (4) |
O1'—C8' | 1.213 (4) | C1'—C2' | 1.387 (4) |
O2'—C8' | 1.325 (4) | C1'—C7' | 1.496 (4) |
O2'—C9' | 1.473 (3) | C2'—C3' | 1.390 (4) |
O3'—N1' | 1.404 (3) | C2'—C20' | 1.500 (4) |
O3'—C10' | 1.430 (3) | C3'—C4' | 1.385 (4) |
O4'—N2' | 1.413 (3) | C3'—H3'A | 0.9300 |
O4'—C20' | 1.449 (3) | C4'—C5' | 1.373 (4) |
N1—C7 | 1.294 (4) | C4'—H4'A | 0.9300 |
N2—C18 | 1.285 (3) | C5'—C6' | 1.388 (4) |
N1'—C7' | 1.275 (3) | C5'—H5'A | 0.9300 |
N2'—C18' | 1.286 (3) | C6'—H6'A | 0.9300 |
C1—C6 | 1.388 (4) | C7'—C8' | 1.501 (5) |
C1—C2 | 1.395 (4) | C9'—H9'A | 0.9600 |
C1—C7 | 1.493 (4) | C9'—H9'B | 0.9600 |
C2—C3 | 1.389 (4) | C9'—H9'C | 0.9600 |
C2—C20 | 1.496 (4) | C10'—H10D | 0.9600 |
C3—C4 | 1.377 (4) | C10'—H10E | 0.9600 |
C3—H3A | 0.9300 | C10'—H10F | 0.9600 |
C4—C5 | 1.368 (4) | C11'—C16' | 1.391 (4) |
C4—H4A | 0.9300 | C11'—C12' | 1.396 (4) |
C5—C6 | 1.382 (4) | C11'—C18' | 1.484 (4) |
C5—H5A | 0.9300 | C12'—C13' | 1.380 (4) |
C6—H6A | 0.9300 | C12'—H12' | 0.9300 |
C7—C8 | 1.496 (4) | C13'—C14' | 1.395 (4) |
C9—H9A | 0.9600 | C13'—C17' | 1.465 (4) |
C9—H9B | 0.9600 | C14'—C15' | 1.374 (4) |
C9—H9C | 0.9600 | C14'—H14' | 0.9300 |
C10—H10A | 0.9600 | C15'—C16' | 1.386 (4) |
C10—H10B | 0.9600 | C15'—H15' | 0.9300 |
C10—H10C | 0.9600 | C16'—H16' | 0.9300 |
C11—C16 | 1.394 (4) | C18'—C19' | 1.495 (4) |
C11—C12 | 1.395 (4) | C19'—H19D | 0.9600 |
C11—C18 | 1.487 (4) | C19'—H19E | 0.9600 |
C12—C13 | 1.375 (4) | C19'—H19F | 0.9600 |
C12—H12B | 0.9300 | C20'—H20C | 0.9700 |
C13—C14 | 1.391 (4) | C20'—H20D | 0.9700 |
C8—O2—C9 | 115.4 (3) | O4—C20—H20A | 110.4 |
N1—O3—C10 | 108.8 (2) | C2—C20—H20A | 110.4 |
N2—O4—C20 | 107.9 (2) | O4—C20—H20B | 110.4 |
C8'—O2'—C9' | 116.9 (3) | C2—C20—H20B | 110.4 |
N1'—O3'—C10' | 108.9 (2) | H20A—C20—H20B | 108.6 |
N2'—O4'—C20' | 108.6 (2) | C6'—C1'—C2' | 120.7 (3) |
C7—N1—O3 | 111.5 (3) | C6'—C1'—C7' | 117.6 (3) |
C18—N2—O4 | 111.8 (3) | C2'—C1'—C7' | 121.7 (3) |
C7'—N1'—O3' | 111.2 (3) | C3'—C2'—C1' | 118.1 (3) |
C18'—N2'—O4' | 110.9 (3) | C3'—C2'—C20' | 119.6 (3) |
C6—C1—C2 | 120.1 (3) | C1'—C2'—C20' | 122.2 (3) |
C6—C1—C7 | 118.2 (3) | C4'—C3'—C2' | 121.1 (3) |
C2—C1—C7 | 121.7 (3) | C4'—C3'—H3'A | 119.4 |
C3—C2—C1 | 118.4 (3) | C2'—C3'—H3'A | 119.4 |
C3—C2—C20 | 118.7 (3) | C5'—C4'—C3' | 120.3 (3) |
C1—C2—C20 | 122.8 (3) | C5'—C4'—H4'A | 119.8 |
C4—C3—C2 | 121.0 (3) | C3'—C4'—H4'A | 119.8 |
C4—C3—H3A | 119.5 | C4'—C5'—C6' | 119.2 (3) |
C2—C3—H3A | 119.5 | C4'—C5'—H5'A | 120.4 |
C5—C4—C3 | 120.3 (3) | C6'—C5'—H5'A | 120.4 |
C5—C4—H4A | 119.9 | C1'—C6'—C5' | 120.5 (3) |
C3—C4—H4A | 119.9 | C1'—C6'—H6'A | 119.8 |
C4—C5—C6 | 120.0 (3) | C5'—C6'—H6'A | 119.8 |
C4—C5—H5A | 120.0 | N1'—C7'—C1' | 118.8 (3) |
C6—C5—H5A | 120.0 | N1'—C7'—C8' | 122.0 (3) |
C5—C6—C1 | 120.2 (3) | C1'—C7'—C8' | 119.0 (3) |
C5—C6—H6A | 119.9 | O1'—C8'—O2' | 125.1 (4) |
C1—C6—H6A | 119.9 | O1'—C8'—C7' | 124.3 (4) |
N1—C7—C1 | 116.4 (3) | O2'—C8'—C7' | 110.5 (3) |
N1—C7—C8 | 122.2 (3) | O2'—C9'—H9'A | 109.5 |
C1—C7—C8 | 121.3 (3) | O2'—C9'—H9'B | 109.5 |
O1—C8—O2 | 125.1 (4) | H9'A—C9'—H9'B | 109.5 |
O1—C8—C7 | 125.5 (4) | O2'—C9'—H9'C | 109.5 |
O2—C8—C7 | 109.5 (3) | H9'A—C9'—H9'C | 109.5 |
O2—C9—H9A | 109.5 | H9'B—C9'—H9'C | 109.5 |
O2—C9—H9B | 109.5 | O3'—C10'—H10D | 109.5 |
H9A—C9—H9B | 109.5 | O3'—C10'—H10E | 109.5 |
O2—C9—H9C | 109.5 | H10D—C10'—H10E | 109.5 |
H9A—C9—H9C | 109.5 | O3'—C10'—H10F | 109.5 |
H9B—C9—H9C | 109.5 | H10D—C10'—H10F | 109.5 |
O3—C10—H10A | 109.5 | H10E—C10'—H10F | 109.5 |
O3—C10—H10B | 109.5 | C16'—C11'—C12' | 118.1 (3) |
H10A—C10—H10B | 109.5 | C16'—C11'—C18' | 120.4 (3) |
O3—C10—H10C | 109.5 | C12'—C11'—C18' | 121.5 (3) |
H10A—C10—H10C | 109.5 | C13'—C12'—C11' | 121.1 (3) |
H10B—C10—H10C | 109.5 | C13'—C12'—H12' | 119.4 |
C16—C11—C12 | 117.7 (3) | C11'—C12'—H12' | 119.4 |
C16—C11—C18 | 121.7 (3) | C12'—C13'—C14' | 120.0 (3) |
C12—C11—C18 | 120.7 (3) | C12'—C13'—C17' | 121.6 (3) |
C13—C12—C11 | 120.5 (3) | C14'—C13'—C17' | 118.4 (3) |
C13—C12—H12B | 119.8 | C15'—C14'—C13' | 119.3 (3) |
C11—C12—H12B | 119.8 | C15'—C14'—H14' | 120.3 |
C12—C13—C14 | 121.5 (3) | C13'—C14'—H14' | 120.3 |
C12—C13—C17 | 120.1 (3) | C14'—C15'—C16' | 120.7 (3) |
C14—C13—C17 | 118.3 (3) | C14'—C15'—H15' | 119.7 |
C15—C14—C13 | 118.3 (3) | C16'—C15'—H15' | 119.7 |
C15—C14—H14A | 120.8 | C15'—C16'—C11' | 120.8 (3) |
C13—C14—H14A | 120.8 | C15'—C16'—H16' | 119.6 |
C14—C15—C16 | 121.1 (3) | C11'—C16'—H16' | 119.6 |
C14—C15—H15A | 119.5 | F1'—C17'—F3' | 106.4 (3) |
C16—C15—H15A | 119.5 | F1'—C17'—F2' | 105.5 (3) |
C15—C16—C11 | 121.0 (3) | F3'—C17'—F2' | 104.0 (3) |
C15—C16—H16A | 119.5 | F1'—C17'—C13' | 114.8 (3) |
C11—C16—H16A | 119.5 | F3'—C17'—C13' | 113.4 (3) |
F1—C17—F3 | 108.2 (3) | F2'—C17'—C13' | 111.9 (3) |
F1—C17—F2 | 104.9 (3) | N2'—C18'—C11' | 115.7 (3) |
F3—C17—F2 | 104.3 (3) | N2'—C18'—C19' | 123.4 (3) |
F1—C17—C13 | 114.3 (3) | C11'—C18'—C19' | 120.9 (3) |
F3—C17—C13 | 113.0 (3) | C18'—C19'—H19D | 109.5 |
F2—C17—C13 | 111.5 (3) | C18'—C19'—H19E | 109.5 |
N2—C18—C11 | 114.8 (3) | H19D—C19'—H19E | 109.5 |
N2—C18—C19 | 125.8 (3) | C18'—C19'—H19F | 109.5 |
C11—C18—C19 | 119.4 (3) | H19D—C19'—H19F | 109.5 |
C18—C19—H19A | 109.5 | H19E—C19'—H19F | 109.5 |
C18—C19—H19B | 109.5 | O4'—C20'—C2' | 106.4 (3) |
H19A—C19—H19B | 109.5 | O4'—C20'—H20C | 110.5 |
C18—C19—H19C | 109.5 | C2'—C20'—H20C | 110.5 |
H19A—C19—H19C | 109.5 | O4'—C20'—H20D | 110.5 |
H19B—C19—H19C | 109.5 | C2'—C20'—H20D | 110.5 |
O4—C20—C2 | 106.7 (3) | H20C—C20'—H20D | 108.6 |
C10—O3—N1—C7 | 173.6 (3) | C3—C2—C20—O4 | −89.8 (3) |
C20—O4—N2—C18 | 179.0 (2) | C1—C2—C20—O4 | 90.3 (4) |
C10'—O3'—N1'—C7' | −177.6 (3) | C6'—C1'—C2'—C3' | −2.1 (5) |
C20'—O4'—N2'—C18' | 175.3 (2) | C7'—C1'—C2'—C3' | 176.9 (3) |
C6—C1—C2—C3 | 1.2 (5) | C6'—C1'—C2'—C20' | −179.2 (3) |
C7—C1—C2—C3 | −176.7 (3) | C7'—C1'—C2'—C20' | −0.1 (5) |
C6—C1—C2—C20 | −178.9 (3) | C1'—C2'—C3'—C4' | 3.2 (5) |
C7—C1—C2—C20 | 3.2 (5) | C20'—C2'—C3'—C4' | −179.7 (3) |
C1—C2—C3—C4 | −0.3 (5) | C2'—C3'—C4'—C5' | −2.0 (5) |
C20—C2—C3—C4 | 179.8 (3) | C3'—C4'—C5'—C6' | −0.3 (5) |
C2—C3—C4—C5 | −1.1 (5) | C2'—C1'—C6'—C5' | −0.1 (5) |
C3—C4—C5—C6 | 1.7 (5) | C7'—C1'—C6'—C5' | −179.2 (3) |
C4—C5—C6—C1 | −0.8 (5) | C4'—C5'—C6'—C1' | 1.3 (5) |
C2—C1—C6—C5 | −0.6 (5) | O3'—N1'—C7'—C1' | −175.0 (3) |
C7—C1—C6—C5 | 177.3 (3) | O3'—N1'—C7'—C8' | 1.0 (4) |
O3—N1—C7—C1 | 174.7 (2) | C6'—C1'—C7'—N1' | 72.4 (4) |
O3—N1—C7—C8 | −0.8 (4) | C2'—C1'—C7'—N1' | −106.7 (4) |
C6—C1—C7—N1 | −51.3 (4) | C6'—C1'—C7'—C8' | −103.7 (4) |
C2—C1—C7—N1 | 126.7 (3) | C2'—C1'—C7'—C8' | 77.2 (4) |
C6—C1—C7—C8 | 124.3 (3) | C9'—O2'—C8'—O1' | −0.7 (5) |
C2—C1—C7—C8 | −57.8 (4) | C9'—O2'—C8'—C7' | −178.8 (3) |
C9—O2—C8—O1 | 0.7 (5) | N1'—C7'—C8'—O1' | 80.4 (5) |
C9—O2—C8—C7 | −178.9 (3) | C1'—C7'—C8'—O1' | −103.6 (4) |
N1—C7—C8—O1 | −70.2 (5) | N1'—C7'—C8'—O2' | −101.4 (4) |
C1—C7—C8—O1 | 114.5 (4) | C1'—C7'—C8'—O2' | 74.6 (4) |
N1—C7—C8—O2 | 109.4 (3) | C16'—C11'—C12'—C13' | −1.6 (5) |
C1—C7—C8—O2 | −65.9 (4) | C18'—C11'—C12'—C13' | 178.7 (3) |
C16—C11—C12—C13 | −1.7 (4) | C11'—C12'—C13'—C14' | 0.9 (5) |
C18—C11—C12—C13 | 178.1 (3) | C11'—C12'—C13'—C17' | −179.4 (3) |
C11—C12—C13—C14 | −0.1 (5) | C12'—C13'—C14'—C15' | −0.2 (5) |
C11—C12—C13—C17 | −178.2 (3) | C17'—C13'—C14'—C15' | −179.9 (3) |
C12—C13—C14—C15 | 1.3 (5) | C13'—C14'—C15'—C16' | 0.3 (5) |
C17—C13—C14—C15 | 179.3 (3) | C14'—C15'—C16'—C11' | −1.1 (5) |
C13—C14—C15—C16 | −0.6 (5) | C12'—C11'—C16'—C15' | 1.8 (5) |
C14—C15—C16—C11 | −1.3 (5) | C18'—C11'—C16'—C15' | −178.6 (3) |
C12—C11—C16—C15 | 2.3 (4) | C12'—C13'—C17'—F1' | −12.8 (5) |
C18—C11—C16—C15 | −177.4 (3) | C14'—C13'—C17'—F1' | 166.9 (3) |
C12—C13—C17—F1 | −20.1 (5) | C12'—C13'—C17'—F3' | −135.5 (3) |
C14—C13—C17—F1 | 161.8 (3) | C14'—C13'—C17'—F3' | 44.3 (5) |
C12—C13—C17—F3 | −144.4 (3) | C12'—C13'—C17'—F2' | 107.3 (4) |
C14—C13—C17—F3 | 37.5 (5) | C14'—C13'—C17'—F2' | −73.0 (4) |
C12—C13—C17—F2 | 98.6 (4) | O4'—N2'—C18'—C11' | 178.5 (3) |
C14—C13—C17—F2 | −79.5 (4) | O4'—N2'—C18'—C19' | −2.6 (4) |
O4—N2—C18—C11 | −179.9 (2) | C16'—C11'—C18'—N2' | 179.2 (3) |
O4—N2—C18—C19 | −0.9 (4) | C12'—C11'—C18'—N2' | −1.2 (5) |
C16—C11—C18—N2 | 169.2 (3) | C16'—C11'—C18'—C19' | 0.3 (5) |
C12—C11—C18—N2 | −10.5 (4) | C12'—C11'—C18'—C19' | 179.9 (3) |
C16—C11—C18—C19 | −9.8 (4) | N2'—O4'—C20'—C2' | 173.9 (2) |
C12—C11—C18—C19 | 170.5 (3) | C3'—C2'—C20'—O4' | −108.0 (3) |
N2—O4—C20—C2 | 171.6 (2) | C1'—C2'—C20'—O4' | 69.0 (4) |