Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807007131/ww2045sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807007131/ww2045Isup2.hkl |
CCDC reference: 604701
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C32H44N2O8 | Dx = 1.297 Mg m−3 |
Mr = 584.69 | Melting point: 224 K |
Trigonal, P3121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 31 2" | Cell parameters from 7233 reflections |
a = 10.8279 (4) Å | θ = 2.2–21.7° |
c = 44.2504 (8) Å | µ = 0.09 mm−1 |
V = 4493.0 (2) Å3 | T = 294 K |
Z = 6 | Block, colourless |
F(000) = 1884 | 0.50 × 0.47 × 0.40 mm |
Bruker SMART CCD area-detector diffractometer | 3107 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.035 |
Graphite monochromator | θmax = 26.5°, θmin = 2.2° |
φ and ω scans | h = −13→13 |
26234 measured reflections | k = −8→13 |
3600 independent reflections | l = −52→55 |
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)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.099 | w = 1/[σ2(Fo2) + (0.0392P)2 + 1.8542P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.008 |
3600 reflections | Δρmax = 0.69 e Å−3 |
387 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0032 (4) |
Experimental. Spectroscopic analysis: 1H NMR (CDCl3, δ, p.p.m., selected signal): 1.10 (t, 3H), 3.26 (s, 6H), 3.36 (s, 3H), 6.98 (t, 1H), 7.46 (t, 1H), 7.90 (d, 1H), 8.64(d, 1H); 13C NMR (CDCl3, δ, p.p.m.): 169.0, 167.3, 141.6, 134.3, 131.0, 122.3, 120.2, 115.7, 90.1, 84.6, 84.1, 82.8, 78.5, 75.6, 61.5, 57.9, 56.5, 56.1, 55.4, 50.9, 49.8, 48.9, 48.5, 47.5, 44.8, 36.2, 31.8, 26.7, 26.2, 25.5, 24.1, 13.5. Analysis, calculated for C32H44N2O8: C 65.72, H 7.59, N 4.79%; found: C 65.99, H 7.56, N 4.58%. |
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 | 0.4155 (3) | 0.7126 (3) | 0.88688 (6) | 0.0384 (6) | |
H1 | 0.3143 | 0.6826 | 0.8848 | 0.046* | |
C2 | 0.4973 (3) | 0.8403 (3) | 0.86626 (6) | 0.0432 (7) | |
H2A | 0.5970 | 0.8905 | 0.8722 | 0.052* | |
H2B | 0.4607 | 0.9051 | 0.8687 | 0.052* | |
C3 | 0.4858 (3) | 0.7977 (3) | 0.83321 (6) | 0.0450 (7) | |
H3A | 0.3885 | 0.7591 | 0.8263 | 0.054* | |
H3B | 0.5471 | 0.8804 | 0.8210 | 0.054* | |
C4 | 0.5307 (3) | 0.6865 (3) | 0.83017 (5) | 0.0360 (6) | |
C5 | 0.4243 (3) | 0.5477 (3) | 0.84610 (5) | 0.0351 (6) | |
H5 | 0.3276 | 0.5096 | 0.8381 | 0.042* | |
C6 | 0.4763 (3) | 0.4392 (3) | 0.84289 (5) | 0.0394 (6) | |
H6A | 0.5446 | 0.4659 | 0.8265 | 0.047* | |
H6B | 0.3970 | 0.3443 | 0.8390 | 0.047* | |
C7 | 0.5473 (3) | 0.4446 (3) | 0.87365 (5) | 0.0338 (6) | |
H7 | 0.6383 | 0.4474 | 0.8705 | 0.041* | |
C8 | 0.4493 (3) | 0.3180 (3) | 0.89370 (6) | 0.0359 (6) | |
C9 | 0.2989 (3) | 0.3040 (3) | 0.89579 (5) | 0.0355 (6) | |
C10 | 0.3089 (3) | 0.4504 (3) | 0.89867 (5) | 0.0339 (6) | |
H10 | 0.2182 | 0.4385 | 0.8913 | 0.041* | |
C11 | 0.4302 (3) | 0.5787 (3) | 0.88074 (5) | 0.0318 (6) | |
C12 | 0.3107 (3) | 0.4715 (3) | 0.93392 (6) | 0.0432 (7) | |
H12A | 0.3953 | 0.5592 | 0.9399 | 0.052* | |
H12B | 0.2273 | 0.4761 | 0.9402 | 0.052* | |
C13 | 0.3103 (3) | 0.3424 (3) | 0.94844 (6) | 0.0394 (6) | |
H13 | 0.2595 | 0.3183 | 0.9678 | 0.047* | |
C14 | 0.2273 (3) | 0.2281 (3) | 0.92513 (6) | 0.0426 (7) | |
H14 | 0.1279 | 0.2064 | 0.9251 | 0.051* | |
C15 | 0.5182 (3) | 0.3271 (3) | 0.92501 (6) | 0.0409 (7) | |
H15A | 0.5084 | 0.2347 | 0.9292 | 0.049* | |
H15B | 0.6194 | 0.3947 | 0.9233 | 0.049* | |
C16 | 0.4620 (3) | 0.3698 (3) | 0.95263 (5) | 0.0411 (6) | |
H16 | 0.5253 | 0.4717 | 0.9565 | 0.049* | |
C17 | 0.5732 (3) | 0.5878 (3) | 0.88748 (5) | 0.0311 (5) | |
H17 | 0.5868 | 0.5877 | 0.9094 | 0.037* | |
C18 | 0.6833 (3) | 0.7360 (3) | 0.84106 (5) | 0.0382 (6) | |
H18A | 0.7197 | 0.6828 | 0.8303 | 0.046* | |
H18B | 0.7437 | 0.8360 | 0.8361 | 0.046* | |
C19 | 0.7826 (4) | 0.9902 (4) | 0.69914 (6) | 0.0512 (8) | |
C20 | 0.8836 (4) | 1.1390 (4) | 0.70960 (7) | 0.0667 (10) | |
H20A | 0.9795 | 1.1634 | 0.7047 | 0.100* | |
H20B | 0.8750 | 1.1448 | 0.7311 | 0.100* | |
H20C | 0.8610 | 1.2043 | 0.6998 | 0.100* | |
C21 | 0.5997 (3) | 0.7338 (3) | 0.77651 (6) | 0.0414 (7) | |
C22 | 0.3952 (6) | 0.8379 (5) | 0.92929 (9) | 0.0957 (16) | |
H22A | 0.4449 | 0.9332 | 0.9214 | 0.144* | |
H22B | 0.4035 | 0.8411 | 0.9509 | 0.144* | |
H22C | 0.2963 | 0.7932 | 0.9238 | 0.144* | |
C23 | 0.1593 (4) | 0.0152 (4) | 0.95286 (8) | 0.0691 (10) | |
H23A | 0.2134 | 0.0612 | 0.9707 | 0.104* | |
H23B | 0.1497 | −0.0775 | 0.9510 | 0.104* | |
H23C | 0.0665 | 0.0057 | 0.9544 | 0.104* | |
C24 | 0.6019 (4) | 0.3355 (5) | 0.98873 (8) | 0.0822 (13) | |
H24A | 0.6508 | 0.3111 | 0.9739 | 0.123* | |
H24B | 0.5971 | 0.2883 | 1.0074 | 0.123* | |
H24C | 0.6526 | 0.4368 | 0.9918 | 0.123* | |
C25 | 0.8305 (3) | 0.7331 (3) | 0.88187 (6) | 0.0418 (7) | |
H25A | 0.8441 | 0.6645 | 0.8704 | 0.050* | |
H25B | 0.8304 | 0.7115 | 0.9031 | 0.050* | |
C26 | 0.9540 (3) | 0.8809 (4) | 0.87572 (8) | 0.0595 (9) | |
H26A | 0.9667 | 0.8959 | 0.8543 | 0.089* | |
H26B | 1.0392 | 0.8901 | 0.8845 | 0.089* | |
H26C | 0.9344 | 0.9505 | 0.8844 | 0.089* | |
C1' | 0.5646 (3) | 0.6655 (3) | 0.74604 (6) | 0.0400 (6) | |
C2' | 0.6298 (3) | 0.7442 (3) | 0.71956 (6) | 0.0412 (7) | |
C3' | 0.5976 (4) | 0.6730 (4) | 0.69187 (6) | 0.0531 (8) | |
H3' | 0.6416 | 0.7230 | 0.6743 | 0.064* | |
C4' | 0.5018 (4) | 0.5299 (4) | 0.69038 (7) | 0.0587 (9) | |
H4' | 0.4812 | 0.4843 | 0.6717 | 0.070* | |
C5' | 0.4348 (4) | 0.4517 (4) | 0.71597 (7) | 0.0577 (8) | |
H5' | 0.3688 | 0.3549 | 0.7146 | 0.069* | |
C6' | 0.4680 (3) | 0.5203 (3) | 0.74357 (6) | 0.0482 (7) | |
H6' | 0.4247 | 0.4681 | 0.7609 | 0.058* | |
N1 | 0.7249 (3) | 0.8911 (3) | 0.72174 (5) | 0.0469 (6) | |
H1A | 0.7506 | 0.9235 | 0.7398 | 0.056* | |
N2 | 0.6922 (2) | 0.7168 (2) | 0.87405 (4) | 0.0332 (5) | |
O1 | 0.7567 (3) | 0.9629 (3) | 0.67265 (5) | 0.0817 (9) | |
O2 | 0.6909 (2) | 0.8559 (2) | 0.78145 (4) | 0.0541 (6) | |
O3 | 0.5170 (2) | 0.6422 (2) | 0.79807 (4) | 0.0436 (5) | |
O4 | 0.2112 (2) | 0.2303 (2) | 0.87038 (4) | 0.0506 (5) | |
H4 | 0.2199 | 0.1612 | 0.8663 | 0.076* | |
O5 | 0.4340 (3) | 0.1928 (2) | 0.87853 (4) | 0.0496 (5) | |
H5A | 0.3864 | 0.1223 | 0.8891 | 0.074* | |
O6 | 0.2307 (2) | 0.0982 (2) | 0.92714 (4) | 0.0484 (5) | |
O7 | 0.4625 (2) | 0.2919 (3) | 0.97851 (4) | 0.0574 (6) | |
O8 | 0.4547 (3) | 0.7594 (2) | 0.91738 (4) | 0.0539 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0394 (16) | 0.0385 (15) | 0.0376 (14) | 0.0197 (13) | −0.0020 (12) | −0.0011 (12) |
C2 | 0.0501 (17) | 0.0348 (15) | 0.0447 (15) | 0.0212 (14) | 0.0018 (13) | 0.0025 (12) |
C3 | 0.0505 (18) | 0.0391 (16) | 0.0424 (15) | 0.0202 (15) | −0.0026 (13) | 0.0084 (12) |
C4 | 0.0407 (15) | 0.0336 (14) | 0.0268 (12) | 0.0133 (12) | −0.0009 (11) | 0.0035 (11) |
C5 | 0.0344 (14) | 0.0328 (14) | 0.0306 (12) | 0.0112 (12) | −0.0021 (11) | 0.0024 (10) |
C6 | 0.0470 (17) | 0.0325 (14) | 0.0314 (13) | 0.0143 (13) | 0.0059 (12) | 0.0024 (11) |
C7 | 0.0368 (14) | 0.0327 (14) | 0.0321 (12) | 0.0175 (12) | 0.0072 (11) | 0.0021 (11) |
C8 | 0.0410 (15) | 0.0304 (14) | 0.0350 (13) | 0.0169 (12) | 0.0056 (12) | 0.0012 (11) |
C9 | 0.0337 (14) | 0.0334 (14) | 0.0327 (13) | 0.0117 (12) | 0.0006 (11) | 0.0036 (11) |
C10 | 0.0272 (13) | 0.0356 (14) | 0.0356 (12) | 0.0132 (11) | 0.0012 (11) | 0.0040 (11) |
C11 | 0.0334 (14) | 0.0305 (13) | 0.0277 (11) | 0.0132 (11) | 0.0012 (10) | 0.0016 (10) |
C12 | 0.0467 (17) | 0.0507 (18) | 0.0362 (14) | 0.0274 (15) | 0.0115 (12) | 0.0078 (12) |
C13 | 0.0377 (15) | 0.0460 (17) | 0.0334 (13) | 0.0202 (13) | 0.0103 (11) | 0.0095 (12) |
C14 | 0.0350 (15) | 0.0415 (16) | 0.0447 (15) | 0.0142 (13) | 0.0069 (12) | 0.0127 (13) |
C15 | 0.0393 (16) | 0.0445 (16) | 0.0405 (14) | 0.0222 (13) | 0.0044 (12) | 0.0099 (12) |
C16 | 0.0393 (15) | 0.0441 (16) | 0.0341 (13) | 0.0167 (13) | 0.0016 (12) | 0.0045 (12) |
C17 | 0.0317 (13) | 0.0299 (13) | 0.0277 (11) | 0.0123 (11) | 0.0025 (10) | 0.0005 (10) |
C18 | 0.0377 (15) | 0.0376 (15) | 0.0313 (12) | 0.0129 (13) | 0.0031 (11) | 0.0045 (11) |
C19 | 0.068 (2) | 0.064 (2) | 0.0378 (15) | 0.0451 (19) | 0.0106 (15) | 0.0111 (14) |
C20 | 0.083 (3) | 0.056 (2) | 0.060 (2) | 0.035 (2) | 0.0161 (19) | 0.0144 (17) |
C21 | 0.0467 (17) | 0.0427 (17) | 0.0311 (13) | 0.0195 (14) | 0.0010 (12) | 0.0067 (12) |
C22 | 0.151 (5) | 0.088 (3) | 0.073 (2) | 0.079 (3) | 0.021 (3) | −0.017 (2) |
C23 | 0.070 (2) | 0.056 (2) | 0.071 (2) | 0.024 (2) | 0.0177 (19) | 0.0315 (18) |
C24 | 0.068 (3) | 0.126 (4) | 0.060 (2) | 0.054 (3) | −0.0140 (19) | 0.011 (2) |
C25 | 0.0344 (15) | 0.0439 (17) | 0.0407 (15) | 0.0147 (13) | −0.0010 (12) | −0.0005 (13) |
C26 | 0.0366 (17) | 0.054 (2) | 0.067 (2) | 0.0064 (16) | −0.0038 (15) | 0.0028 (16) |
C1' | 0.0411 (16) | 0.0455 (16) | 0.0332 (13) | 0.0216 (13) | −0.0022 (12) | 0.0008 (12) |
C2' | 0.0424 (16) | 0.0554 (18) | 0.0319 (13) | 0.0290 (15) | −0.0004 (11) | 0.0033 (13) |
C3' | 0.060 (2) | 0.069 (2) | 0.0352 (14) | 0.0361 (19) | 0.0023 (14) | −0.0025 (15) |
C4' | 0.072 (2) | 0.072 (2) | 0.0393 (16) | 0.041 (2) | −0.0084 (15) | −0.0147 (16) |
C5' | 0.059 (2) | 0.053 (2) | 0.0558 (18) | 0.0233 (17) | −0.0102 (16) | −0.0165 (16) |
C6' | 0.0512 (19) | 0.0464 (18) | 0.0442 (15) | 0.0222 (16) | −0.0022 (13) | −0.0021 (13) |
N1 | 0.0545 (16) | 0.0521 (16) | 0.0310 (11) | 0.0244 (14) | 0.0018 (11) | 0.0047 (11) |
N2 | 0.0304 (11) | 0.0326 (12) | 0.0310 (10) | 0.0115 (10) | 0.0005 (9) | 0.0016 (9) |
O1 | 0.134 (3) | 0.0785 (18) | 0.0354 (11) | 0.0550 (19) | 0.0027 (14) | 0.0103 (11) |
O2 | 0.0623 (14) | 0.0415 (12) | 0.0353 (10) | 0.0087 (11) | 0.0024 (10) | 0.0024 (9) |
O3 | 0.0526 (12) | 0.0381 (10) | 0.0275 (9) | 0.0134 (10) | 0.0004 (8) | 0.0034 (8) |
O4 | 0.0490 (12) | 0.0406 (12) | 0.0454 (11) | 0.0098 (10) | −0.0091 (10) | −0.0015 (9) |
O5 | 0.0634 (15) | 0.0318 (11) | 0.0505 (11) | 0.0215 (11) | 0.0150 (10) | 0.0036 (9) |
O6 | 0.0513 (13) | 0.0361 (11) | 0.0494 (11) | 0.0156 (10) | 0.0080 (10) | 0.0136 (9) |
O7 | 0.0553 (14) | 0.0825 (17) | 0.0367 (10) | 0.0361 (13) | 0.0019 (9) | 0.0165 (11) |
O8 | 0.0817 (17) | 0.0462 (12) | 0.0375 (10) | 0.0348 (12) | −0.0004 (10) | −0.0051 (9) |
C1—O8 | 1.429 (3) | C17—H17 | 0.9800 |
C1—C2 | 1.517 (4) | C18—N2 | 1.484 (3) |
C1—C11 | 1.559 (4) | C18—H18A | 0.9700 |
C1—H1 | 0.9800 | C18—H18B | 0.9700 |
C2—C3 | 1.520 (4) | C19—O1 | 1.207 (3) |
C2—H2A | 0.9700 | C19—N1 | 1.368 (4) |
C2—H2B | 0.9700 | C19—C20 | 1.498 (5) |
C3—C4 | 1.512 (4) | C20—H20A | 0.9600 |
C3—H3A | 0.9700 | C20—H20B | 0.9600 |
C3—H3B | 0.9700 | C20—H20C | 0.9600 |
C4—O3 | 1.483 (3) | C21—O2 | 1.211 (4) |
C4—C5 | 1.533 (4) | C21—O3 | 1.345 (3) |
C4—C18 | 1.538 (4) | C21—C1' | 1.493 (4) |
C5—C6 | 1.543 (4) | C22—O8 | 1.401 (4) |
C5—C11 | 1.563 (3) | C22—H22A | 0.9600 |
C5—H5 | 0.9800 | C22—H22B | 0.9600 |
C6—C7 | 1.550 (4) | C22—H22C | 0.9600 |
C6—H6A | 0.9700 | C23—O6 | 1.417 (3) |
C6—H6B | 0.9700 | C23—H23A | 0.9600 |
C7—C8 | 1.529 (4) | C23—H23B | 0.9600 |
C7—C17 | 1.557 (4) | C23—H23C | 0.9600 |
C7—H7 | 0.9800 | C24—O7 | 1.412 (4) |
C8—O5 | 1.446 (3) | C24—H24A | 0.9600 |
C8—C15 | 1.553 (4) | C24—H24B | 0.9600 |
C8—C9 | 1.561 (4) | C24—H24C | 0.9600 |
C9—O4 | 1.430 (3) | C25—N2 | 1.459 (4) |
C9—C14 | 1.524 (3) | C25—C26 | 1.511 (4) |
C9—C10 | 1.539 (4) | C25—H25A | 0.9700 |
C10—C11 | 1.569 (3) | C25—H25B | 0.9700 |
C10—C12 | 1.575 (3) | C26—H26A | 0.9600 |
C10—H10 | 0.9800 | C26—H26B | 0.9600 |
C11—C17 | 1.531 (4) | C26—H26C | 0.9600 |
C12—C13 | 1.537 (4) | C1'—C6' | 1.390 (4) |
C12—H12A | 0.9700 | C1'—C2' | 1.413 (4) |
C12—H12B | 0.9700 | C2'—C3' | 1.396 (4) |
C13—C14 | 1.514 (4) | C2'—N1 | 1.401 (4) |
C13—C16 | 1.527 (4) | C3'—C4' | 1.369 (5) |
C13—H13 | 0.9800 | C3'—H3' | 0.9300 |
C14—O6 | 1.428 (3) | C4'—C5' | 1.382 (5) |
C14—H14 | 0.9800 | C4'—H4' | 0.9300 |
C15—C16 | 1.536 (4) | C5'—C6' | 1.380 (4) |
C15—H15A | 0.9700 | C5'—H5' | 0.9300 |
C15—H15B | 0.9700 | C6'—H6' | 0.9300 |
C16—O7 | 1.425 (3) | N1—H1A | 0.8600 |
C16—H16 | 0.9800 | O4—H4 | 0.8200 |
C17—N2 | 1.471 (3) | O5—H5A | 0.8200 |
O8—C1—C2 | 108.1 (2) | O7—C16—C13 | 107.7 (2) |
O8—C1—C11 | 110.1 (2) | O7—C16—C15 | 110.0 (2) |
C2—C1—C11 | 117.3 (2) | C13—C16—C15 | 113.2 (2) |
O8—C1—H1 | 107.0 | O7—C16—H16 | 108.6 |
C2—C1—H1 | 107.0 | C13—C16—H16 | 108.6 |
C11—C1—H1 | 107.0 | C15—C16—H16 | 108.6 |
C1—C2—C3 | 112.3 (2) | N2—C17—C11 | 111.1 (2) |
C1—C2—H2A | 109.1 | N2—C17—C7 | 115.0 (2) |
C3—C2—H2A | 109.1 | C11—C17—C7 | 100.8 (2) |
C1—C2—H2B | 109.1 | N2—C17—H17 | 109.9 |
C3—C2—H2B | 109.1 | C11—C17—H17 | 109.9 |
H2A—C2—H2B | 107.9 | C7—C17—H17 | 109.9 |
C4—C3—C2 | 108.5 (2) | N2—C18—C4 | 113.1 (2) |
C4—C3—H3A | 110.0 | N2—C18—H18A | 109.0 |
C2—C3—H3A | 110.0 | C4—C18—H18A | 109.0 |
C4—C3—H3B | 110.0 | N2—C18—H18B | 109.0 |
C2—C3—H3B | 110.0 | C4—C18—H18B | 109.0 |
H3A—C3—H3B | 108.4 | H18A—C18—H18B | 107.8 |
O3—C4—C3 | 108.8 (2) | O1—C19—N1 | 124.0 (3) |
O3—C4—C5 | 102.6 (2) | O1—C19—C20 | 121.3 (3) |
C3—C4—C5 | 110.9 (2) | N1—C19—C20 | 114.8 (3) |
O3—C4—C18 | 109.2 (2) | C19—C20—H20A | 109.5 |
C3—C4—C18 | 114.3 (2) | C19—C20—H20B | 109.5 |
C5—C4—C18 | 110.3 (2) | H20A—C20—H20B | 109.5 |
C4—C5—C6 | 108.8 (2) | C19—C20—H20C | 109.5 |
C4—C5—C11 | 108.1 (2) | H20A—C20—H20C | 109.5 |
C6—C5—C11 | 105.2 (2) | H20B—C20—H20C | 109.5 |
C4—C5—H5 | 111.5 | O2—C21—O3 | 123.8 (2) |
C6—C5—H5 | 111.5 | O2—C21—C1' | 124.8 (2) |
C11—C5—H5 | 111.5 | O3—C21—C1' | 111.4 (3) |
C5—C6—C7 | 104.7 (2) | O8—C22—H22A | 109.5 |
C5—C6—H6A | 110.8 | O8—C22—H22B | 109.5 |
C7—C6—H6A | 110.8 | H22A—C22—H22B | 109.5 |
C5—C6—H6B | 110.8 | O8—C22—H22C | 109.5 |
C7—C6—H6B | 110.8 | H22A—C22—H22C | 109.5 |
H6A—C6—H6B | 108.9 | H22B—C22—H22C | 109.5 |
C8—C7—C6 | 111.5 (2) | O6—C23—H23A | 109.5 |
C8—C7—C17 | 111.3 (2) | O6—C23—H23B | 109.5 |
C6—C7—C17 | 102.8 (2) | H23A—C23—H23B | 109.5 |
C8—C7—H7 | 110.3 | O6—C23—H23C | 109.5 |
C6—C7—H7 | 110.3 | H23A—C23—H23C | 109.5 |
C17—C7—H7 | 110.3 | H23B—C23—H23C | 109.5 |
O5—C8—C7 | 105.9 (2) | O7—C24—H24A | 109.5 |
O5—C8—C15 | 107.5 (2) | O7—C24—H24B | 109.5 |
C7—C8—C15 | 111.4 (2) | H24A—C24—H24B | 109.5 |
O5—C8—C9 | 108.2 (2) | O7—C24—H24C | 109.5 |
C7—C8—C9 | 110.1 (2) | H24A—C24—H24C | 109.5 |
C15—C8—C9 | 113.5 (2) | H24B—C24—H24C | 109.5 |
O4—C9—C14 | 110.6 (2) | N2—C25—C26 | 113.4 (3) |
O4—C9—C10 | 108.9 (2) | N2—C25—H25A | 108.9 |
C14—C9—C10 | 103.8 (2) | C26—C25—H25A | 108.9 |
O4—C9—C8 | 112.2 (2) | N2—C25—H25B | 108.9 |
C14—C9—C8 | 109.1 (2) | C26—C25—H25B | 108.9 |
C10—C9—C8 | 111.9 (2) | H25A—C25—H25B | 107.7 |
C9—C10—C11 | 117.8 (2) | C25—C26—H26A | 109.5 |
C9—C10—C12 | 102.8 (2) | C25—C26—H26B | 109.5 |
C11—C10—C12 | 115.4 (2) | H26A—C26—H26B | 109.5 |
C9—C10—H10 | 106.7 | C25—C26—H26C | 109.5 |
C11—C10—H10 | 106.7 | H26A—C26—H26C | 109.5 |
C12—C10—H10 | 106.7 | H26B—C26—H26C | 109.5 |
C17—C11—C1 | 118.4 (2) | C6'—C1'—C2' | 118.9 (3) |
C17—C11—C5 | 97.84 (19) | C6'—C1'—C21 | 119.5 (3) |
C1—C11—C5 | 111.0 (2) | C2'—C1'—C21 | 121.6 (3) |
C17—C11—C10 | 109.3 (2) | C3'—C2'—N1 | 121.8 (3) |
C1—C11—C10 | 107.8 (2) | C3'—C2'—C1' | 118.9 (3) |
C5—C11—C10 | 112.3 (2) | N1—C2'—C1' | 119.4 (2) |
C13—C12—C10 | 106.7 (2) | C4'—C3'—C2' | 120.4 (3) |
C13—C12—H12A | 110.4 | C4'—C3'—H3' | 119.8 |
C10—C12—H12A | 110.4 | C2'—C3'—H3' | 119.8 |
C13—C12—H12B | 110.4 | C3'—C4'—C5' | 121.5 (3) |
C10—C12—H12B | 110.4 | C3'—C4'—H4' | 119.3 |
H12A—C12—H12B | 108.6 | C5'—C4'—H4' | 119.3 |
C14—C13—C16 | 112.5 (2) | C6'—C5'—C4' | 118.7 (3) |
C14—C13—C12 | 100.9 (2) | C6'—C5'—H5' | 120.7 |
C16—C13—C12 | 111.1 (2) | C4'—C5'—H5' | 120.7 |
C14—C13—H13 | 110.6 | C5'—C6'—C1' | 121.6 (3) |
C16—C13—H13 | 110.6 | C5'—C6'—H6' | 119.2 |
C12—C13—H13 | 110.6 | C1'—C6'—H6' | 119.2 |
O6—C14—C13 | 117.7 (2) | C19—N1—C2' | 128.9 (2) |
O6—C14—C9 | 109.1 (2) | C19—N1—H1A | 115.5 |
C13—C14—C9 | 101.9 (2) | C2'—N1—H1A | 115.5 |
O6—C14—H14 | 109.2 | C25—N2—C17 | 112.2 (2) |
C13—C14—H14 | 109.2 | C25—N2—C18 | 110.5 (2) |
C9—C14—H14 | 109.2 | C17—N2—C18 | 116.3 (2) |
C16—C15—C8 | 118.6 (2) | C21—O3—C4 | 121.3 (2) |
C16—C15—H15A | 107.7 | C9—O4—H4 | 109.5 |
C8—C15—H15A | 107.7 | C8—O5—H5A | 109.5 |
C16—C15—H15B | 107.7 | C23—O6—C14 | 113.6 (2) |
C8—C15—H15B | 107.7 | C24—O7—C16 | 112.3 (3) |
H15A—C15—H15B | 107.1 | C22—O8—C1 | 115.2 (3) |
O8—C1—C2—C3 | 168.9 (2) | C8—C9—C14—O6 | −52.2 (3) |
C11—C1—C2—C3 | 43.8 (4) | O4—C9—C14—C13 | −163.2 (2) |
C1—C2—C3—C4 | −53.7 (3) | C10—C9—C14—C13 | −46.4 (3) |
C2—C3—C4—O3 | 178.9 (2) | C8—C9—C14—C13 | 73.0 (3) |
C2—C3—C4—C5 | 66.7 (3) | O5—C8—C15—C16 | −138.9 (3) |
C2—C3—C4—C18 | −58.8 (3) | C7—C8—C15—C16 | 105.5 (3) |
O3—C4—C5—C6 | 65.1 (2) | C9—C8—C15—C16 | −19.4 (4) |
C3—C4—C5—C6 | −178.9 (2) | C14—C13—C16—O7 | −98.1 (3) |
C18—C4—C5—C6 | −51.2 (3) | C12—C13—C16—O7 | 149.6 (2) |
O3—C4—C5—C11 | 178.8 (2) | C14—C13—C16—C15 | 23.8 (3) |
C3—C4—C5—C11 | −65.1 (3) | C12—C13—C16—C15 | −88.5 (3) |
C18—C4—C5—C11 | 62.5 (3) | C8—C15—C16—O7 | 143.1 (3) |
C4—C5—C6—C7 | 100.7 (2) | C8—C15—C16—C13 | 22.5 (4) |
C11—C5—C6—C7 | −14.9 (3) | C1—C11—C17—N2 | −49.2 (3) |
C5—C6—C7—C8 | 101.7 (2) | C5—C11—C17—N2 | 69.8 (2) |
C5—C6—C7—C17 | −17.7 (3) | C10—C11—C17—N2 | −173.18 (18) |
C6—C7—C8—O5 | 65.9 (3) | C1—C11—C17—C7 | −171.6 (2) |
C17—C7—C8—O5 | −179.9 (2) | C5—C11—C17—C7 | −52.5 (2) |
C6—C7—C8—C15 | −177.6 (2) | C10—C11—C17—C7 | 64.5 (2) |
C17—C7—C8—C15 | −63.4 (3) | C8—C7—C17—N2 | 165.6 (2) |
C6—C7—C8—C9 | −50.8 (3) | C6—C7—C17—N2 | −74.9 (3) |
C17—C7—C8—C9 | 63.4 (3) | C8—C7—C17—C11 | −74.9 (2) |
O5—C8—C9—O4 | −33.0 (3) | C6—C7—C17—C11 | 44.6 (2) |
C7—C8—C9—O4 | 82.3 (3) | O3—C4—C18—N2 | −152.6 (2) |
C15—C8—C9—O4 | −152.1 (2) | C3—C4—C18—N2 | 85.3 (3) |
O5—C8—C9—C14 | 90.0 (2) | C5—C4—C18—N2 | −40.5 (3) |
C7—C8—C9—C14 | −154.8 (2) | O2—C21—C1'—C6' | 173.3 (3) |
C15—C8—C9—C14 | −29.2 (3) | O3—C21—C1'—C6' | −6.6 (4) |
O5—C8—C9—C10 | −155.72 (19) | O2—C21—C1'—C2' | −5.2 (5) |
C7—C8—C9—C10 | −40.5 (3) | O3—C21—C1'—C2' | 174.9 (3) |
C15—C8—C9—C10 | 85.2 (3) | C6'—C1'—C2'—C3' | −1.5 (4) |
O4—C9—C10—C11 | −88.2 (3) | C21—C1'—C2'—C3' | 177.0 (3) |
C14—C9—C10—C11 | 153.9 (2) | C6'—C1'—C2'—N1 | 178.7 (3) |
C8—C9—C10—C11 | 36.4 (3) | C21—C1'—C2'—N1 | −2.9 (4) |
O4—C9—C10—C12 | 143.8 (2) | N1—C2'—C3'—C4' | −178.5 (3) |
C14—C9—C10—C12 | 25.9 (3) | C1'—C2'—C3'—C4' | 1.6 (5) |
C8—C9—C10—C12 | −91.6 (2) | C2'—C3'—C4'—C5' | −0.4 (5) |
O8—C1—C11—C17 | −54.3 (3) | C3'—C4'—C5'—C6' | −1.0 (5) |
C2—C1—C11—C17 | 69.8 (3) | C4'—C5'—C6'—C1' | 1.1 (5) |
O8—C1—C11—C5 | −166.3 (2) | C2'—C1'—C6'—C5' | 0.1 (5) |
C2—C1—C11—C5 | −42.2 (3) | C21—C1'—C6'—C5' | −178.4 (3) |
O8—C1—C11—C10 | 70.4 (3) | O1—C19—N1—C2' | 0.7 (5) |
C2—C1—C11—C10 | −165.6 (2) | C20—C19—N1—C2' | −178.9 (3) |
C4—C5—C11—C17 | −74.2 (2) | C3'—C2'—N1—C19 | 11.0 (5) |
C6—C5—C11—C17 | 41.9 (2) | C1'—C2'—N1—C19 | −169.1 (3) |
C4—C5—C11—C1 | 50.3 (3) | C26—C25—N2—C17 | −164.6 (2) |
C6—C5—C11—C1 | 166.5 (2) | C26—C25—N2—C18 | 63.8 (3) |
C4—C5—C11—C10 | 171.1 (2) | C11—C17—N2—C25 | 176.1 (2) |
C6—C5—C11—C10 | −72.7 (3) | C7—C17—N2—C25 | −70.3 (3) |
C9—C10—C11—C17 | −51.1 (3) | C11—C17—N2—C18 | −55.3 (3) |
C12—C10—C11—C17 | 70.7 (3) | C7—C17—N2—C18 | 58.3 (3) |
C9—C10—C11—C1 | 178.9 (2) | C4—C18—N2—C25 | 166.6 (2) |
C12—C10—C11—C1 | −59.3 (3) | C4—C18—N2—C17 | 37.2 (3) |
C9—C10—C11—C5 | 56.3 (3) | O2—C21—O3—C4 | 1.0 (5) |
C12—C10—C11—C5 | 178.1 (2) | C1'—C21—O3—C4 | −179.1 (2) |
C9—C10—C12—C13 | 3.1 (3) | C3—C4—O3—C21 | 65.8 (3) |
C11—C10—C12—C13 | −126.5 (2) | C5—C4—O3—C21 | −176.6 (2) |
C10—C12—C13—C14 | −30.9 (3) | C18—C4—O3—C21 | −59.5 (3) |
C10—C12—C13—C16 | 88.6 (3) | C13—C14—O6—C23 | 68.1 (3) |
C16—C13—C14—O6 | 47.8 (3) | C9—C14—O6—C23 | −176.6 (3) |
C12—C13—C14—O6 | 166.3 (2) | C13—C16—O7—C24 | −165.8 (3) |
C16—C13—C14—C9 | −71.4 (3) | C15—C16—O7—C24 | 70.4 (4) |
C12—C13—C14—C9 | 47.1 (3) | C2—C1—O8—C22 | 75.0 (4) |
O4—C9—C14—O6 | 71.7 (3) | C11—C1—O8—C22 | −155.8 (3) |
C10—C9—C14—O6 | −171.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O2 | 0.86 | 1.97 | 2.668 (3) | 138 |
O4—H4···O5 | 0.82 | 2.23 | 2.665 (3) | 113 |
O5—H5A···O6 | 0.82 | 2.30 | 2.875 (3) | 127 |