Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S010827011301367X/fa3316sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S010827011301367X/fa3316Isup2.hkl |
CCDC reference: 950463
For related literature, see: Abboud et al. (1997); Allen (2002); Bernstein et al. (1995); Bishop et al. (2007); Cremer & Pople (1975); Lee et al. (2004); Lortat-Jacob (2009); Mohammadi et al. (2005); Patey et al. (2008); Piecewicz & Sengupta (2011); Scholefield et al. (2003); Schwörer et al. (2013); Turnbull et al. (2001).
4-Methoxyphenyl 4-O-[6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(9-fluorenylmethyloxycarbonyl)-α-D-glucopyranosyl]-2-O-benzoyl-3-O-benzyl-6-O-chloroacetyl-β-D-glucopyranoside was prepared as described in our recent publication (Schwörer et al., 2013). Good quality single crystals suitable for diffraction analysis were obtained by vapour diffusion of petroleum ether into a solution of the title compound in toluene.
Molecule 2 (primed labels) has conformational disorder at benzyl atom C38'; this was handled by refining two sites [A:B 0.53 (3):0.47 (3)] and equal bond-length restraints (for bonds to atoms O13' and C39').
The methyl H atoms were constrained to an ideal geometry (C—H = 0.98 Å), with Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the adjacent C—C bonds. All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances of 0.95 (aromatic), 0.99 (methylene) or 1.00 Å (tertiary) and with Uiso(H) = 1.5Ueq(C) for methyl H atoms or 1.2Ueq(C) otherwise.
Data collection: CrystalClear (Rigaku, 2005); cell refinement: FSProcess (Rigaku, 1998); data reduction: FSProcess (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 in WinGX (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008).
C59H56ClN3O16 | F(000) = 2304 |
Mr = 1098.52 | Dx = 1.367 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2yb | Cell parameters from 14490 reflections |
a = 10.454 (2) Å | θ = 6.6–71.4° |
b = 35.610 (7) Å | µ = 1.27 mm−1 |
c = 14.408 (3) Å | T = 123 K |
β = 95.61 (3)° | Needle, colourless |
V = 5338.0 (19) Å3 | 0.80 × 0.08 × 0.04 mm |
Z = 4 |
Rigaku Spider diffractometer | 12625 independent reflections |
Radiation source: Rigaku MM007 rotating anode | 8360 reflections with I > 2σ(I) |
Rigaku VariMax-HF Confocal Optical System monochromator | Rint = 0.055 |
Detector resolution: 10 pixels mm-1 | θmax = 55.0°, θmin = 6.5° |
ω scans | h = −10→8 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −37→37 |
Tmin = 0.68, Tmax = 1.0 | l = −15→15 |
35705 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)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.155 | w = 1/[σ2(Fo2) + (0.0772P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.00 | (Δ/σ)max = 0.004 |
12625 reflections | Δρmax = 0.32 e Å−3 |
1426 parameters | Δρmin = −0.30 e Å−3 |
3 restraints | Absolute structure: Flack x determined using 2859 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.035 (11) |
C59H56ClN3O16 | V = 5338.0 (19) Å3 |
Mr = 1098.52 | Z = 4 |
Monoclinic, P21 | Cu Kα radiation |
a = 10.454 (2) Å | µ = 1.27 mm−1 |
b = 35.610 (7) Å | T = 123 K |
c = 14.408 (3) Å | 0.80 × 0.08 × 0.04 mm |
β = 95.61 (3)° |
Rigaku Spider diffractometer | 12625 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 8360 reflections with I > 2σ(I) |
Tmin = 0.68, Tmax = 1.0 | Rint = 0.055 |
35705 measured reflections | θmax = 55.0° |
R[F2 > 2σ(F2)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.155 | Δρmax = 0.32 e Å−3 |
S = 1.00 | Δρmin = −0.30 e Å−3 |
12625 reflections | Absolute structure: Flack x determined using 2859 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004) |
1426 parameters | Absolute structure parameter: 0.035 (11) |
3 restraints |
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) | |
Cl1 | 0.3721 (2) | 0.56035 (6) | −0.17482 (15) | 0.0525 (6) | |
O1 | 0.0708 (5) | 0.54608 (14) | 0.1382 (4) | 0.0406 (15) | |
O2 | 0.0576 (5) | 0.50177 (13) | 0.3051 (4) | 0.0374 (14) | |
O3 | −0.0424 (5) | 0.42837 (13) | 0.2564 (3) | 0.0400 (14) | |
O4 | 0.1048 (5) | 0.39301 (12) | 0.1148 (3) | 0.0349 (13) | |
O5 | 0.1257 (5) | 0.49274 (13) | 0.0647 (3) | 0.0339 (13) | |
O6 | −0.1390 (6) | 0.52700 (17) | 0.3069 (4) | 0.0549 (17) | |
O7 | 0.4317 (6) | 0.65918 (15) | 0.1252 (4) | 0.0562 (17) | |
O8 | 0.3110 (5) | 0.46699 (14) | −0.0451 (4) | 0.0387 (14) | |
O9 | 0.1818 (6) | 0.50036 (16) | −0.1501 (4) | 0.0507 (16) | |
O10 | −0.0643 (5) | 0.36376 (13) | 0.0231 (4) | 0.0404 (15) | |
O11 | −0.0929 (5) | 0.38857 (16) | −0.1726 (4) | 0.0504 (16) | |
O12 | 0.0660 (9) | 0.3812 (2) | −0.2623 (6) | 0.102 (3) | |
O13 | 0.2099 (5) | 0.28054 (15) | 0.1022 (4) | 0.0532 (16) | |
O14 | 0.1591 (5) | 0.30329 (14) | −0.0874 (4) | 0.0448 (15) | |
O15 | 0.0641 (6) | 0.24722 (14) | −0.1193 (4) | 0.0522 (17) | |
O16 | 0.2558 (5) | 0.26371 (13) | −0.1670 (4) | 0.0411 (15) | |
N1 | 0.1279 (8) | 0.3355 (2) | 0.2381 (5) | 0.059 (2) | |
N2 | 0.1594 (8) | 0.3059 (3) | 0.2808 (6) | 0.066 (2) | |
N3 | 0.1936 (9) | 0.2815 (2) | 0.3290 (6) | 0.091 (3) | |
C1 | 0.1219 (8) | 0.5101 (2) | 0.1529 (5) | 0.035 (2) | |
H1 | 0.2102 | 0.5115 | 0.1864 | 0.042* | |
C2 | 0.0327 (8) | 0.4886 (2) | 0.2104 (5) | 0.032 (2) | |
H2 | −0.0588 | 0.4937 | 0.1868 | 0.039* | |
C3 | 0.0570 (8) | 0.4465 (2) | 0.2118 (5) | 0.036 (2) | |
H3 | 0.1408 | 0.4416 | 0.2495 | 0.043* | |
C4 | 0.0660 (8) | 0.4317 (2) | 0.1131 (5) | 0.031 (2) | |
H4 | −0.0182 | 0.4348 | 0.0745 | 0.038* | |
C5 | 0.1688 (8) | 0.4547 (2) | 0.0729 (5) | 0.033 (2) | |
H5 | 0.2480 | 0.4540 | 0.1178 | 0.040* | |
C6 | 0.1643 (9) | 0.5739 (2) | 0.1304 (6) | 0.038 (2) | |
C7 | 0.1974 (9) | 0.5960 (2) | 0.2074 (6) | 0.049 (2) | |
H7 | 0.1586 | 0.5918 | 0.2634 | 0.058* | |
C8 | 0.2878 (10) | 0.6243 (2) | 0.2029 (6) | 0.055 (3) | |
H8 | 0.3102 | 0.6398 | 0.2557 | 0.066* | |
C9 | 0.3451 (9) | 0.6300 (2) | 0.1219 (6) | 0.044 (2) | |
C10 | 0.3133 (8) | 0.6082 (2) | 0.0450 (6) | 0.044 (2) | |
H10 | 0.3535 | 0.6120 | −0.0106 | 0.052* | |
C11 | 0.2205 (8) | 0.5801 (2) | 0.0499 (6) | 0.043 (2) | |
H11 | 0.1961 | 0.5652 | −0.0035 | 0.052* | |
C12 | 0.4977 (9) | 0.6652 (2) | 0.0450 (6) | 0.051 (2) | |
H12A | 0.5514 | 0.6433 | 0.0348 | 0.076* | |
H12B | 0.5521 | 0.6876 | 0.0543 | 0.076* | |
H12C | 0.4352 | 0.6688 | −0.0095 | 0.076* | |
C13 | −0.0350 (10) | 0.5203 (2) | 0.3461 (6) | 0.041 (2) | |
C14 | 0.0093 (9) | 0.5312 (2) | 0.4439 (6) | 0.040 (2) | |
C15 | 0.1246 (9) | 0.5179 (2) | 0.4914 (6) | 0.046 (2) | |
H15 | 0.1822 | 0.5032 | 0.4595 | 0.055* | |
C16 | 0.1528 (9) | 0.5262 (2) | 0.5834 (6) | 0.054 (3) | |
H16 | 0.2290 | 0.5164 | 0.6159 | 0.064* | |
C17 | 0.0733 (10) | 0.5485 (3) | 0.6299 (6) | 0.054 (3) | |
H17 | 0.0946 | 0.5540 | 0.6941 | 0.065* | |
C18 | −0.0379 (9) | 0.5628 (3) | 0.5835 (6) | 0.056 (3) | |
H18 | −0.0920 | 0.5787 | 0.6155 | 0.067* | |
C19 | −0.0707 (9) | 0.5542 (2) | 0.4904 (6) | 0.048 (2) | |
H19 | −0.1475 | 0.5639 | 0.4586 | 0.058* | |
C20 | 0.0068 (9) | 0.4138 (2) | 0.3468 (6) | 0.050 (2) | |
H20A | 0.0570 | 0.4335 | 0.3824 | 0.061* | |
H20B | 0.0648 | 0.3923 | 0.3385 | 0.061* | |
C21 | −0.1031 (8) | 0.4011 (3) | 0.4009 (6) | 0.046 (2) | |
C22 | −0.1549 (10) | 0.3652 (2) | 0.3911 (7) | 0.065 (3) | |
H22 | −0.1271 | 0.3484 | 0.3458 | 0.078* | |
C23 | −0.2476 (10) | 0.3541 (3) | 0.4482 (8) | 0.072 (3) | |
H23 | −0.2824 | 0.3295 | 0.4420 | 0.087* | |
C24 | −0.2904 (10) | 0.3782 (3) | 0.5141 (7) | 0.063 (3) | |
H24 | −0.3538 | 0.3700 | 0.5526 | 0.075* | |
C25 | −0.2412 (10) | 0.4136 (3) | 0.5234 (6) | 0.059 (3) | |
H25 | −0.2700 | 0.4302 | 0.5685 | 0.071* | |
C26 | −0.1484 (9) | 0.4253 (3) | 0.4666 (6) | 0.057 (3) | |
H26 | −0.1153 | 0.4501 | 0.4726 | 0.068* | |
C27 | 0.2051 (8) | 0.4430 (2) | −0.0222 (5) | 0.037 (2) | |
H27A | 0.2319 | 0.4163 | −0.0211 | 0.045* | |
H27B | 0.1306 | 0.4460 | −0.0696 | 0.045* | |
C28 | 0.2828 (10) | 0.4967 (2) | −0.1025 (6) | 0.040 (2) | |
C29 | 0.3972 (9) | 0.5219 (2) | −0.0969 (6) | 0.045 (2) | |
H29A | 0.4732 | 0.5074 | −0.1122 | 0.054* | |
H29B | 0.4147 | 0.5315 | −0.0324 | 0.054* | |
C30 | 0.0026 (8) | 0.3673 (2) | 0.1125 (6) | 0.041 (2) | |
H30 | −0.0590 | 0.3759 | 0.1569 | 0.050* | |
C31 | 0.0137 (8) | 0.3510 (2) | −0.0486 (6) | 0.039 (2) | |
H31 | 0.0860 | 0.3691 | −0.0538 | 0.047* | |
C32 | 0.0685 (8) | 0.3123 (2) | −0.0205 (6) | 0.042 (2) | |
H32 | −0.0012 | 0.2930 | −0.0216 | 0.051* | |
C33 | 0.1433 (9) | 0.3145 (2) | 0.0752 (6) | 0.042 (2) | |
H33 | 0.2112 | 0.3340 | 0.0702 | 0.051* | |
C34 | 0.0579 (9) | 0.3292 (2) | 0.1460 (6) | 0.046 (2) | |
H34 | −0.0140 | 0.3111 | 0.1519 | 0.055* | |
C35 | −0.0730 (8) | 0.3505 (2) | −0.1399 (6) | 0.045 (2) | |
H35A | −0.0325 | 0.3355 | −0.1870 | 0.054* | |
H35B | −0.1565 | 0.3388 | −0.1301 | 0.054* | |
C36 | −0.0181 (12) | 0.4003 (3) | −0.2373 (7) | 0.061 (3) | |
C37 | −0.0472 (11) | 0.4399 (2) | −0.2697 (6) | 0.070 (3) | |
H37A | 0.0178 | 0.4569 | −0.2397 | 0.105* | |
H37B | −0.1323 | 0.4472 | −0.2531 | 0.105* | |
H37C | −0.0458 | 0.4412 | −0.3376 | 0.105* | |
C38 | 0.1364 (9) | 0.2490 (2) | 0.1149 (6) | 0.055 (3) | |
H38A | 0.0924 | 0.2409 | 0.0542 | 0.066* | |
H38B | 0.0699 | 0.2550 | 0.1569 | 0.066* | |
C39 | 0.2212 (10) | 0.2169 (2) | 0.1569 (6) | 0.048 (2) | |
C40 | 0.3482 (10) | 0.2154 (3) | 0.1464 (7) | 0.065 (3) | |
H40 | 0.3877 | 0.2346 | 0.1134 | 0.078* | |
C41 | 0.4196 (10) | 0.1857 (3) | 0.1840 (7) | 0.080 (3) | |
H41 | 0.5092 | 0.1852 | 0.1777 | 0.096* | |
C42 | 0.3672 (12) | 0.1569 (3) | 0.2300 (8) | 0.073 (3) | |
H42 | 0.4186 | 0.1366 | 0.2549 | 0.088* | |
C43 | 0.2371 (11) | 0.1582 (3) | 0.2392 (7) | 0.069 (3) | |
H43 | 0.1972 | 0.1383 | 0.2696 | 0.083* | |
C44 | 0.1643 (9) | 0.1887 (2) | 0.2040 (6) | 0.061 (3) | |
H44 | 0.0754 | 0.1901 | 0.2124 | 0.073* | |
C45 | 0.1517 (9) | 0.2685 (2) | −0.1237 (6) | 0.039 (2) | |
C46 | 0.2670 (9) | 0.2282 (2) | −0.2166 (6) | 0.044 (2) | |
H46A | 0.1859 | 0.2138 | −0.2173 | 0.053* | |
H46B | 0.3373 | 0.2129 | −0.1851 | 0.053* | |
C47 | 0.2945 (8) | 0.2369 (2) | −0.3141 (5) | 0.038 (2) | |
H47 | 0.3731 | 0.2530 | −0.3132 | 0.045* | |
C48 | 0.1830 (8) | 0.2554 (2) | −0.3737 (6) | 0.043 (2) | |
C49 | 0.1250 (9) | 0.2893 (2) | −0.3624 (7) | 0.050 (2) | |
H49 | 0.1564 | 0.3058 | −0.3137 | 0.060* | |
C50 | 0.0188 (9) | 0.2992 (2) | −0.4240 (7) | 0.049 (2) | |
H50 | −0.0235 | 0.3224 | −0.4162 | 0.059* | |
C51 | −0.0256 (9) | 0.2754 (3) | −0.4963 (7) | 0.063 (3) | |
H51 | −0.0986 | 0.2824 | −0.5371 | 0.075* | |
C52 | 0.0350 (10) | 0.2416 (3) | −0.5099 (7) | 0.061 (3) | |
H52 | 0.0053 | 0.2256 | −0.5602 | 0.073* | |
C53 | 0.1408 (9) | 0.2315 (2) | −0.4481 (6) | 0.047 (2) | |
C54 | 0.2217 (9) | 0.1981 (2) | −0.4443 (6) | 0.045 (2) | |
C55 | 0.2201 (10) | 0.1666 (3) | −0.5028 (7) | 0.061 (3) | |
H55 | 0.1567 | 0.1645 | −0.5545 | 0.074* | |
C56 | 0.3092 (11) | 0.1392 (3) | −0.4855 (7) | 0.060 (3) | |
H56 | 0.3092 | 0.1181 | −0.5257 | 0.072* | |
C57 | 0.4004 (10) | 0.1420 (2) | −0.4092 (7) | 0.059 (3) | |
H57 | 0.4614 | 0.1224 | −0.3972 | 0.071* | |
C58 | 0.4048 (9) | 0.1732 (2) | −0.3490 (6) | 0.047 (2) | |
H58 | 0.4684 | 0.1752 | −0.2974 | 0.057* | |
C59 | 0.3138 (8) | 0.2006 (2) | −0.3676 (6) | 0.038 (2) | |
Cl1' | 0.8734 (2) | 0.55843 (6) | −0.17030 (15) | 0.0507 (6) | |
O1' | 0.5652 (5) | 0.54277 (13) | 0.1374 (4) | 0.0379 (14) | |
O2' | 0.5560 (5) | 0.49745 (13) | 0.3056 (3) | 0.0335 (13) | |
O3' | 0.4489 (5) | 0.42561 (13) | 0.2541 (3) | 0.0372 (14) | |
O4' | 0.5858 (5) | 0.38958 (12) | 0.1085 (3) | 0.0358 (14) | |
O5' | 0.6249 (5) | 0.48969 (13) | 0.0639 (3) | 0.0341 (13) | |
O6' | 0.3658 (6) | 0.52717 (16) | 0.3064 (4) | 0.0532 (17) | |
O7' | 0.9216 (6) | 0.65691 (14) | 0.1232 (4) | 0.0482 (16) | |
O8' | 0.8106 (5) | 0.46457 (13) | −0.0421 (4) | 0.0362 (14) | |
O9' | 0.6835 (6) | 0.49837 (15) | −0.1474 (4) | 0.0458 (15) | |
O10' | 0.4205 (5) | 0.36731 (13) | 0.0002 (4) | 0.0406 (14) | |
O11' | 0.4092 (6) | 0.39306 (15) | −0.1921 (4) | 0.0509 (16) | |
O12' | 0.5749 (9) | 0.3859 (2) | −0.2771 (6) | 0.105 (3) | |
O13' | 0.6259 (5) | 0.27235 (15) | 0.0858 (4) | 0.0505 (16) | |
O14' | 0.6458 (6) | 0.30377 (14) | −0.0995 (4) | 0.0453 (15) | |
O15' | 0.5545 (6) | 0.24825 (15) | −0.1437 (4) | 0.0532 (17) | |
O16' | 0.7589 (5) | 0.26364 (13) | −0.1669 (4) | 0.0432 (15) | |
N1' | 0.5654 (9) | 0.3277 (2) | 0.2197 (6) | 0.070 (3) | |
N2' | 0.5365 (9) | 0.2986 (3) | 0.2561 (6) | 0.086 (3) | |
N3' | 0.5164 (13) | 0.2712 (3) | 0.3034 (7) | 0.140 (5) | |
C1' | 0.6187 (8) | 0.50718 (19) | 0.1530 (5) | 0.035 (2) | |
H1' | 0.7064 | 0.5091 | 0.1873 | 0.042* | |
C2' | 0.5290 (8) | 0.48507 (19) | 0.2099 (5) | 0.0290 (19) | |
H2' | 0.4377 | 0.4910 | 0.1873 | 0.035* | |
C3' | 0.5497 (8) | 0.4428 (2) | 0.2082 (5) | 0.033 (2) | |
H3' | 0.6334 | 0.4371 | 0.2453 | 0.040* | |
C4' | 0.5576 (8) | 0.4291 (2) | 0.1095 (5) | 0.031 (2) | |
H4' | 0.4747 | 0.4343 | 0.0710 | 0.038* | |
C5' | 0.6660 (8) | 0.45167 (19) | 0.0720 (5) | 0.033 (2) | |
H5' | 0.7436 | 0.4503 | 0.1183 | 0.039* | |
C6' | 0.6569 (8) | 0.5716 (2) | 0.1288 (6) | 0.036 (2) | |
C7' | 0.6934 (8) | 0.5923 (2) | 0.2083 (6) | 0.041 (2) | |
H7' | 0.6582 | 0.5871 | 0.2652 | 0.049* | |
C8' | 0.7817 (8) | 0.6208 (2) | 0.2031 (6) | 0.042 (2) | |
H8' | 0.8070 | 0.6356 | 0.2567 | 0.051* | |
C9' | 0.8337 (8) | 0.6279 (2) | 0.1200 (6) | 0.038 (2) | |
C10' | 0.7972 (8) | 0.6072 (2) | 0.0410 (6) | 0.042 (2) | |
H10' | 0.8328 | 0.6123 | −0.0159 | 0.050* | |
C12' | 0.9852 (9) | 0.6629 (2) | 0.0418 (6) | 0.051 (3) | |
H12D | 1.0344 | 0.6404 | 0.0286 | 0.077* | |
H12E | 1.0437 | 0.6844 | 0.0517 | 0.077* | |
H12F | 0.9215 | 0.6681 | −0.0112 | 0.077* | |
C11' | 0.7061 (8) | 0.5786 (2) | 0.0468 (6) | 0.041 (2) | |
H11' | 0.6788 | 0.5641 | −0.0069 | 0.049* | |
C13' | 0.4684 (9) | 0.5183 (2) | 0.3457 (6) | 0.038 (2) | |
C14' | 0.5133 (9) | 0.5284 (2) | 0.4439 (6) | 0.039 (2) | |
C15' | 0.6234 (9) | 0.5123 (2) | 0.4908 (6) | 0.049 (2) | |
H15' | 0.6758 | 0.4958 | 0.4590 | 0.059* | |
C16' | 0.6548 (9) | 0.5206 (3) | 0.5833 (7) | 0.057 (3) | |
H16' | 0.7283 | 0.5092 | 0.6158 | 0.068* | |
C17' | 0.5812 (10) | 0.5453 (2) | 0.6303 (6) | 0.052 (3) | |
H17' | 0.6039 | 0.5506 | 0.6944 | 0.062* | |
C18' | 0.4748 (10) | 0.5621 (3) | 0.5833 (6) | 0.054 (3) | |
H18' | 0.4249 | 0.5794 | 0.6147 | 0.065* | |
C19' | 0.4406 (9) | 0.5536 (2) | 0.4883 (6) | 0.049 (2) | |
H19' | 0.3678 | 0.5652 | 0.4555 | 0.059* | |
C20' | 0.4989 (8) | 0.4082 (2) | 0.3408 (5) | 0.046 (2) | |
H20C | 0.5631 | 0.4250 | 0.3743 | 0.055* | |
H20D | 0.5428 | 0.3845 | 0.3273 | 0.055* | |
C21' | 0.3935 (8) | 0.4000 (2) | 0.4021 (5) | 0.036 (2) | |
C22' | 0.3494 (9) | 0.3645 (2) | 0.4133 (6) | 0.044 (2) | |
H22' | 0.3804 | 0.3447 | 0.3773 | 0.052* | |
C23' | 0.2598 (9) | 0.3564 (3) | 0.4762 (6) | 0.051 (3) | |
H23' | 0.2295 | 0.3315 | 0.4824 | 0.061* | |
C24' | 0.2163 (9) | 0.3845 (3) | 0.5287 (6) | 0.051 (2) | |
H24' | 0.1556 | 0.3792 | 0.5718 | 0.062* | |
C25' | 0.2602 (9) | 0.4210 (2) | 0.5195 (6) | 0.048 (2) | |
H25' | 0.2309 | 0.4406 | 0.5569 | 0.058* | |
C26' | 0.3470 (9) | 0.4287 (2) | 0.4554 (6) | 0.046 (2) | |
H26' | 0.3753 | 0.4537 | 0.4478 | 0.056* | |
C27' | 0.7042 (8) | 0.4402 (2) | −0.0225 (5) | 0.036 (2) | |
H27C | 0.7315 | 0.4135 | −0.0216 | 0.044* | |
H27D | 0.6310 | 0.4433 | −0.0708 | 0.044* | |
C28' | 0.7830 (9) | 0.4946 (2) | −0.0981 (6) | 0.037 (2) | |
C29' | 0.8958 (8) | 0.5205 (2) | −0.0899 (6) | 0.043 (2) | |
H29C | 0.9740 | 0.5063 | −0.1018 | 0.052* | |
H29D | 0.9085 | 0.5305 | −0.0256 | 0.052* | |
C30' | 0.4747 (9) | 0.3671 (2) | 0.0941 (6) | 0.043 (2) | |
H30' | 0.4093 | 0.3765 | 0.1347 | 0.052* | |
C31' | 0.5016 (9) | 0.3530 (2) | −0.0673 (6) | 0.043 (2) | |
H31' | 0.5792 | 0.3694 | −0.0681 | 0.051* | |
C32' | 0.5440 (8) | 0.3129 (2) | −0.0409 (6) | 0.043 (2) | |
H32' | 0.4705 | 0.2950 | −0.0523 | 0.051* | |
C33' | 0.6020 (9) | 0.3108 (2) | 0.0591 (6) | 0.046 (2) | |
H33' | 0.6843 | 0.3253 | 0.0666 | 0.055* | |
C34' | 0.5098 (8) | 0.3268 (2) | 0.1215 (6) | 0.043 (2) | |
H34' | 0.4299 | 0.3112 | 0.1166 | 0.052* | |
C35' | 0.4241 (9) | 0.3546 (2) | −0.1617 (6) | 0.048 (2) | |
H35C | 0.4684 | 0.3400 | −0.2076 | 0.058* | |
H35D | 0.3385 | 0.3432 | −0.1574 | 0.058* | |
C36' | 0.4887 (12) | 0.4049 (3) | −0.2526 (7) | 0.064 (3) | |
C37' | 0.4640 (11) | 0.4450 (2) | −0.2813 (6) | 0.070 (3) | |
H37D | 0.5255 | 0.4614 | −0.2450 | 0.105* | |
H37E | 0.3764 | 0.4520 | −0.2698 | 0.105* | |
H37F | 0.4742 | 0.4478 | −0.3479 | 0.105* | |
C39' | 0.7781 (8) | 0.2269 (2) | 0.1516 (7) | 0.050 (3) | |
C40' | 0.7923 (8) | 0.1918 (3) | 0.1117 (7) | 0.062 (3) | |
H40' | 0.7897 | 0.1894 | 0.0459 | 0.074* | |
C41' | 0.8101 (10) | 0.1605 (3) | 0.1677 (10) | 0.077 (4) | |
H41' | 0.8185 | 0.1367 | 0.1394 | 0.092* | |
C42' | 0.8159 (11) | 0.1625 (4) | 0.2596 (11) | 0.087 (4) | |
H42' | 0.8289 | 0.1407 | 0.2971 | 0.105* | |
C43' | 0.8027 (11) | 0.1970 (4) | 0.2990 (8) | 0.095 (4) | |
H43' | 0.8077 | 0.1990 | 0.3651 | 0.114* | |
C44' | 0.7821 (9) | 0.2292 (3) | 0.2458 (8) | 0.071 (3) | |
H44' | 0.7710 | 0.2527 | 0.2750 | 0.085* | |
C45' | 0.6430 (10) | 0.2691 (2) | −0.1380 (6) | 0.044 (2) | |
C46' | 0.7772 (8) | 0.22839 (19) | −0.2155 (6) | 0.041 (2) | |
H46C | 0.6992 | 0.2126 | −0.2154 | 0.049* | |
H46D | 0.8506 | 0.2144 | −0.1835 | 0.049* | |
C47' | 0.8030 (8) | 0.2369 (2) | −0.3146 (5) | 0.036 (2) | |
H47' | 0.8803 | 0.2534 | −0.3158 | 0.044* | |
C48' | 0.6883 (8) | 0.2539 (2) | −0.3728 (6) | 0.042 (2) | |
C49' | 0.6323 (9) | 0.2881 (2) | −0.3640 (6) | 0.047 (2) | |
H49' | 0.6687 | 0.3059 | −0.3198 | 0.056* | |
C50' | 0.5189 (9) | 0.2966 (3) | −0.4218 (7) | 0.053 (3) | |
H50' | 0.4757 | 0.3198 | −0.4151 | 0.064* | |
C51' | 0.4714 (9) | 0.2707 (3) | −0.4883 (7) | 0.054 (3) | |
H51' | 0.3958 | 0.2767 | −0.5276 | 0.065* | |
C52' | 0.5296 (9) | 0.2369 (2) | −0.4993 (6) | 0.049 (2) | |
H52' | 0.4959 | 0.2198 | −0.5460 | 0.059* | |
C53' | 0.6390 (9) | 0.2282 (2) | −0.4409 (6) | 0.043 (2) | |
C54' | 0.7206 (9) | 0.1946 (2) | −0.4358 (6) | 0.046 (2) | |
C55' | 0.7159 (9) | 0.1615 (2) | −0.4887 (6) | 0.049 (2) | |
H55' | 0.6470 | 0.1574 | −0.5356 | 0.059* | |
C56' | 0.8113 (10) | 0.1350 (3) | −0.4725 (7) | 0.054 (3) | |
H56' | 0.8080 | 0.1126 | −0.5085 | 0.065* | |
C57' | 0.9125 (10) | 0.1408 (2) | −0.4037 (7) | 0.058 (3) | |
H57' | 0.9791 | 0.1227 | −0.3941 | 0.070* | |
C58' | 0.9169 (9) | 0.1733 (2) | −0.3483 (6) | 0.046 (2) | |
H58' | 0.9844 | 0.1768 | −0.3000 | 0.056* | |
C59' | 0.8222 (8) | 0.2000 (2) | −0.3650 (6) | 0.038 (2) | |
C38A | 0.7496 (17) | 0.2566 (6) | 0.0753 (17) | 0.054 (4)* | 0.53 (3) |
H38C | 0.8163 | 0.2790 | 0.0915 | 0.065* | 0.53 (3) |
H38D | 0.7605 | 0.2488 | 0.0151 | 0.065* | 0.53 (3) |
C38B | 0.7667 (16) | 0.2676 (6) | 0.117 (2) | 0.054 (4)* | 0.47 (3) |
H38E | 0.8326 | 0.2753 | 0.0699 | 0.065* | 0.47 (3) |
H38F | 0.8020 | 0.2875 | 0.1740 | 0.065* | 0.47 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0679 (17) | 0.0462 (13) | 0.0446 (14) | −0.0031 (12) | 0.0122 (12) | 0.0083 (11) |
O1 | 0.044 (4) | 0.024 (3) | 0.054 (4) | 0.002 (3) | 0.005 (3) | −0.003 (3) |
O2 | 0.036 (3) | 0.041 (3) | 0.036 (3) | 0.006 (3) | 0.007 (3) | −0.005 (3) |
O3 | 0.047 (4) | 0.041 (3) | 0.032 (3) | 0.001 (3) | 0.003 (3) | 0.004 (3) |
O4 | 0.042 (4) | 0.019 (3) | 0.043 (3) | 0.000 (3) | 0.004 (3) | −0.003 (2) |
O5 | 0.040 (4) | 0.034 (3) | 0.029 (3) | 0.007 (3) | 0.003 (3) | −0.002 (3) |
O6 | 0.049 (4) | 0.068 (4) | 0.047 (4) | 0.022 (3) | −0.002 (3) | −0.018 (3) |
O7 | 0.084 (5) | 0.040 (4) | 0.047 (4) | −0.017 (3) | 0.015 (4) | −0.008 (3) |
O8 | 0.041 (4) | 0.034 (3) | 0.042 (4) | −0.002 (3) | 0.009 (3) | 0.000 (3) |
O9 | 0.047 (4) | 0.062 (4) | 0.042 (4) | 0.002 (3) | 0.001 (3) | 0.011 (3) |
O10 | 0.046 (4) | 0.041 (3) | 0.035 (4) | −0.004 (3) | 0.009 (3) | −0.011 (3) |
O11 | 0.056 (4) | 0.050 (4) | 0.046 (4) | 0.002 (3) | 0.009 (3) | −0.004 (3) |
O12 | 0.129 (8) | 0.072 (5) | 0.117 (7) | 0.014 (5) | 0.073 (6) | 0.005 (5) |
O13 | 0.061 (4) | 0.026 (3) | 0.073 (4) | −0.005 (3) | 0.007 (3) | −0.002 (3) |
O14 | 0.047 (4) | 0.032 (3) | 0.057 (4) | −0.008 (3) | 0.012 (3) | −0.003 (3) |
O15 | 0.049 (4) | 0.032 (3) | 0.078 (5) | −0.012 (3) | 0.015 (3) | −0.012 (3) |
O16 | 0.034 (4) | 0.035 (3) | 0.056 (4) | −0.002 (3) | 0.015 (3) | −0.010 (3) |
N1 | 0.084 (6) | 0.039 (5) | 0.051 (5) | 0.006 (4) | −0.001 (4) | 0.010 (4) |
N2 | 0.080 (7) | 0.059 (6) | 0.060 (6) | −0.018 (5) | 0.012 (5) | 0.000 (5) |
N3 | 0.138 (9) | 0.067 (6) | 0.069 (7) | 0.008 (6) | 0.012 (6) | 0.017 (5) |
C1 | 0.040 (5) | 0.029 (5) | 0.035 (5) | 0.007 (4) | 0.010 (4) | −0.005 (4) |
C2 | 0.034 (5) | 0.036 (5) | 0.027 (5) | −0.001 (4) | 0.001 (4) | −0.006 (4) |
C3 | 0.042 (6) | 0.034 (5) | 0.031 (5) | 0.005 (4) | 0.001 (4) | 0.008 (4) |
C4 | 0.031 (5) | 0.031 (5) | 0.033 (5) | 0.000 (4) | 0.006 (4) | −0.001 (4) |
C5 | 0.040 (6) | 0.029 (5) | 0.030 (5) | 0.010 (4) | 0.007 (4) | −0.009 (4) |
C6 | 0.060 (6) | 0.023 (4) | 0.028 (5) | 0.009 (4) | −0.002 (5) | −0.005 (4) |
C7 | 0.070 (7) | 0.039 (5) | 0.039 (6) | −0.004 (5) | 0.014 (5) | 0.002 (4) |
C8 | 0.086 (8) | 0.042 (5) | 0.039 (6) | −0.011 (5) | 0.011 (5) | −0.012 (5) |
C9 | 0.061 (7) | 0.029 (5) | 0.042 (6) | 0.003 (5) | 0.002 (5) | −0.003 (5) |
C10 | 0.043 (6) | 0.040 (5) | 0.049 (6) | −0.001 (5) | 0.015 (5) | −0.005 (5) |
C11 | 0.048 (6) | 0.042 (5) | 0.040 (6) | 0.002 (5) | 0.010 (5) | −0.013 (4) |
C12 | 0.057 (6) | 0.039 (5) | 0.054 (7) | −0.001 (5) | 0.000 (5) | −0.005 (5) |
C13 | 0.053 (7) | 0.030 (5) | 0.040 (6) | 0.006 (5) | 0.012 (5) | 0.005 (4) |
C14 | 0.053 (6) | 0.027 (5) | 0.040 (6) | 0.003 (4) | 0.013 (5) | 0.001 (4) |
C15 | 0.052 (7) | 0.047 (6) | 0.041 (6) | 0.017 (5) | 0.011 (5) | 0.005 (5) |
C16 | 0.066 (7) | 0.053 (6) | 0.042 (6) | 0.002 (5) | 0.003 (5) | 0.002 (5) |
C17 | 0.071 (8) | 0.063 (6) | 0.030 (6) | −0.010 (6) | 0.011 (5) | −0.008 (5) |
C18 | 0.052 (7) | 0.070 (7) | 0.048 (7) | 0.004 (6) | 0.018 (5) | −0.010 (5) |
C19 | 0.055 (6) | 0.053 (6) | 0.038 (6) | 0.004 (5) | 0.011 (5) | −0.005 (5) |
C20 | 0.053 (6) | 0.061 (6) | 0.038 (6) | 0.010 (5) | 0.006 (5) | 0.009 (5) |
C21 | 0.045 (6) | 0.057 (6) | 0.037 (6) | 0.007 (5) | 0.008 (5) | 0.010 (5) |
C22 | 0.068 (7) | 0.035 (6) | 0.097 (9) | 0.008 (5) | 0.034 (7) | 0.012 (5) |
C23 | 0.052 (7) | 0.051 (6) | 0.115 (10) | 0.011 (5) | 0.017 (7) | 0.028 (7) |
C24 | 0.063 (7) | 0.077 (8) | 0.050 (7) | 0.015 (7) | 0.016 (5) | 0.027 (6) |
C25 | 0.064 (8) | 0.085 (8) | 0.031 (6) | −0.002 (6) | 0.015 (5) | −0.003 (5) |
C26 | 0.056 (7) | 0.068 (7) | 0.045 (6) | −0.009 (6) | 0.001 (5) | −0.002 (5) |
C27 | 0.043 (6) | 0.032 (4) | 0.038 (5) | −0.010 (4) | 0.009 (4) | 0.002 (4) |
C28 | 0.061 (7) | 0.031 (5) | 0.030 (5) | 0.006 (5) | 0.009 (5) | 0.003 (4) |
C29 | 0.056 (7) | 0.039 (5) | 0.041 (6) | −0.007 (5) | 0.010 (5) | 0.014 (4) |
C30 | 0.063 (7) | 0.027 (5) | 0.035 (5) | −0.003 (5) | 0.016 (5) | −0.004 (4) |
C31 | 0.043 (6) | 0.031 (5) | 0.044 (6) | −0.009 (4) | 0.014 (5) | −0.008 (4) |
C32 | 0.051 (6) | 0.029 (5) | 0.050 (6) | −0.003 (4) | 0.024 (5) | −0.007 (4) |
C33 | 0.057 (6) | 0.028 (5) | 0.040 (6) | −0.002 (4) | −0.002 (5) | −0.007 (4) |
C34 | 0.069 (7) | 0.034 (5) | 0.034 (6) | −0.007 (5) | 0.003 (5) | 0.000 (4) |
C35 | 0.049 (6) | 0.041 (5) | 0.043 (6) | −0.014 (4) | −0.001 (5) | −0.004 (4) |
C36 | 0.082 (9) | 0.055 (7) | 0.046 (7) | −0.003 (6) | 0.006 (6) | −0.014 (6) |
C37 | 0.104 (9) | 0.050 (6) | 0.053 (7) | −0.002 (6) | −0.004 (6) | −0.004 (5) |
C38 | 0.063 (7) | 0.047 (6) | 0.057 (6) | −0.012 (5) | 0.015 (5) | −0.008 (5) |
C39 | 0.060 (7) | 0.024 (5) | 0.060 (7) | 0.005 (5) | 0.005 (5) | 0.002 (5) |
C40 | 0.069 (8) | 0.039 (6) | 0.089 (8) | 0.005 (6) | 0.015 (6) | 0.007 (5) |
C41 | 0.074 (8) | 0.053 (7) | 0.116 (10) | 0.007 (6) | 0.018 (7) | −0.005 (7) |
C42 | 0.094 (10) | 0.039 (6) | 0.088 (9) | 0.011 (6) | 0.010 (7) | 0.012 (6) |
C43 | 0.086 (9) | 0.040 (6) | 0.082 (8) | −0.011 (6) | 0.011 (7) | 0.020 (6) |
C44 | 0.065 (7) | 0.043 (6) | 0.074 (7) | 0.003 (5) | 0.001 (6) | 0.009 (5) |
C45 | 0.054 (7) | 0.020 (5) | 0.044 (6) | −0.003 (5) | 0.008 (5) | 0.000 (4) |
C46 | 0.048 (6) | 0.026 (5) | 0.057 (6) | −0.003 (4) | 0.002 (5) | −0.012 (4) |
C47 | 0.042 (6) | 0.031 (5) | 0.041 (5) | −0.006 (4) | 0.008 (4) | −0.007 (4) |
C48 | 0.048 (6) | 0.036 (5) | 0.047 (6) | −0.006 (5) | 0.021 (5) | 0.006 (5) |
C49 | 0.050 (6) | 0.040 (5) | 0.062 (7) | −0.003 (5) | 0.010 (5) | 0.013 (5) |
C50 | 0.043 (6) | 0.040 (5) | 0.065 (7) | 0.001 (5) | 0.014 (5) | 0.014 (5) |
C51 | 0.041 (6) | 0.077 (8) | 0.073 (8) | 0.003 (6) | 0.013 (6) | 0.021 (7) |
C52 | 0.060 (7) | 0.064 (7) | 0.056 (7) | 0.002 (6) | −0.003 (6) | 0.007 (5) |
C53 | 0.057 (7) | 0.046 (6) | 0.040 (6) | −0.009 (5) | 0.010 (5) | 0.005 (5) |
C54 | 0.052 (6) | 0.043 (6) | 0.043 (6) | −0.005 (5) | 0.016 (5) | −0.002 (5) |
C55 | 0.067 (8) | 0.058 (7) | 0.062 (7) | −0.003 (6) | 0.016 (6) | −0.012 (6) |
C56 | 0.079 (8) | 0.051 (7) | 0.051 (7) | −0.009 (6) | 0.015 (6) | −0.021 (5) |
C57 | 0.070 (8) | 0.037 (6) | 0.078 (8) | 0.000 (5) | 0.040 (6) | −0.005 (6) |
C58 | 0.057 (7) | 0.034 (5) | 0.054 (6) | −0.002 (5) | 0.020 (5) | 0.001 (5) |
C59 | 0.036 (5) | 0.038 (5) | 0.040 (6) | −0.003 (4) | 0.006 (4) | 0.000 (4) |
Cl1' | 0.0654 (16) | 0.0437 (13) | 0.0442 (14) | −0.0035 (11) | 0.0119 (12) | 0.0116 (11) |
O1' | 0.044 (4) | 0.021 (3) | 0.049 (4) | 0.000 (3) | 0.007 (3) | −0.001 (3) |
O2' | 0.032 (3) | 0.038 (3) | 0.032 (3) | 0.003 (3) | 0.009 (3) | 0.001 (3) |
O3' | 0.040 (4) | 0.038 (3) | 0.033 (3) | −0.005 (3) | 0.004 (3) | 0.008 (3) |
O4' | 0.049 (4) | 0.016 (3) | 0.042 (3) | 0.000 (3) | 0.005 (3) | −0.003 (2) |
O5' | 0.048 (4) | 0.027 (3) | 0.028 (3) | 0.005 (3) | 0.006 (3) | 0.000 (2) |
O6' | 0.046 (4) | 0.062 (4) | 0.050 (4) | 0.021 (3) | −0.001 (3) | −0.013 (3) |
O7' | 0.064 (4) | 0.033 (3) | 0.051 (4) | −0.012 (3) | 0.019 (3) | −0.004 (3) |
O8' | 0.038 (4) | 0.032 (3) | 0.040 (3) | 0.001 (3) | 0.011 (3) | 0.001 (3) |
O9' | 0.044 (4) | 0.050 (4) | 0.044 (4) | 0.001 (3) | 0.006 (3) | 0.007 (3) |
O10' | 0.047 (4) | 0.028 (3) | 0.047 (4) | −0.003 (3) | 0.009 (3) | −0.006 (3) |
O11' | 0.066 (5) | 0.041 (4) | 0.048 (4) | 0.001 (3) | 0.019 (3) | −0.001 (3) |
O12' | 0.117 (7) | 0.093 (6) | 0.114 (7) | 0.000 (6) | 0.063 (6) | 0.006 (5) |
O13' | 0.050 (4) | 0.031 (3) | 0.071 (4) | 0.003 (3) | 0.007 (3) | 0.002 (3) |
O14' | 0.052 (4) | 0.030 (3) | 0.056 (4) | −0.005 (3) | 0.014 (3) | −0.006 (3) |
O15' | 0.056 (4) | 0.028 (3) | 0.077 (5) | −0.003 (3) | 0.013 (4) | −0.015 (3) |
O16' | 0.033 (4) | 0.036 (3) | 0.062 (4) | 0.001 (3) | 0.012 (3) | −0.008 (3) |
N1' | 0.132 (8) | 0.025 (4) | 0.060 (6) | −0.002 (5) | 0.036 (5) | 0.020 (4) |
N2' | 0.108 (8) | 0.093 (8) | 0.059 (7) | 0.030 (7) | 0.011 (6) | −0.010 (6) |
N3' | 0.242 (15) | 0.092 (8) | 0.094 (9) | 0.015 (8) | 0.053 (9) | 0.031 (7) |
C1' | 0.040 (5) | 0.027 (5) | 0.040 (5) | 0.005 (4) | 0.012 (4) | −0.001 (4) |
C2' | 0.031 (5) | 0.030 (4) | 0.026 (5) | 0.006 (4) | 0.005 (4) | 0.003 (4) |
C3' | 0.036 (5) | 0.035 (5) | 0.028 (5) | 0.002 (4) | 0.000 (4) | 0.007 (4) |
C4' | 0.036 (5) | 0.029 (5) | 0.029 (5) | 0.001 (4) | 0.003 (4) | 0.001 (4) |
C5' | 0.049 (6) | 0.023 (4) | 0.027 (5) | 0.002 (4) | 0.006 (4) | −0.001 (4) |
C6' | 0.048 (6) | 0.017 (4) | 0.043 (6) | 0.000 (4) | 0.002 (5) | −0.003 (4) |
C7' | 0.057 (6) | 0.028 (5) | 0.038 (6) | −0.001 (4) | 0.012 (5) | 0.003 (4) |
C8' | 0.057 (6) | 0.029 (5) | 0.041 (6) | −0.010 (4) | 0.004 (5) | −0.006 (4) |
C9' | 0.052 (6) | 0.023 (5) | 0.040 (6) | 0.006 (4) | 0.007 (5) | 0.003 (4) |
C10' | 0.044 (6) | 0.033 (5) | 0.052 (6) | −0.004 (4) | 0.015 (5) | −0.004 (4) |
C12' | 0.070 (7) | 0.037 (5) | 0.051 (6) | −0.001 (5) | 0.021 (5) | 0.001 (4) |
C11' | 0.057 (6) | 0.034 (5) | 0.035 (5) | 0.003 (4) | 0.018 (5) | −0.012 (4) |
C13' | 0.048 (6) | 0.031 (5) | 0.038 (6) | 0.004 (5) | 0.011 (5) | 0.003 (4) |
C14' | 0.048 (6) | 0.033 (5) | 0.038 (6) | −0.001 (4) | 0.014 (5) | −0.001 (4) |
C15' | 0.049 (6) | 0.062 (6) | 0.037 (6) | 0.014 (5) | 0.011 (5) | 0.005 (5) |
C16' | 0.059 (7) | 0.064 (7) | 0.048 (6) | 0.003 (6) | 0.008 (5) | 0.003 (5) |
C17' | 0.068 (7) | 0.054 (6) | 0.034 (6) | −0.020 (6) | 0.007 (5) | −0.003 (5) |
C18' | 0.067 (7) | 0.061 (6) | 0.036 (6) | 0.001 (6) | 0.015 (5) | −0.001 (5) |
C19' | 0.061 (7) | 0.046 (6) | 0.041 (6) | 0.009 (5) | 0.003 (5) | 0.000 (5) |
C20' | 0.052 (6) | 0.055 (6) | 0.032 (5) | 0.003 (5) | 0.011 (5) | 0.010 (5) |
C21' | 0.040 (6) | 0.035 (5) | 0.032 (5) | 0.003 (4) | −0.001 (4) | 0.006 (4) |
C22' | 0.056 (6) | 0.036 (5) | 0.040 (5) | 0.003 (5) | 0.005 (5) | 0.002 (4) |
C23' | 0.051 (7) | 0.047 (6) | 0.056 (6) | 0.004 (5) | 0.008 (5) | 0.016 (5) |
C24' | 0.046 (6) | 0.057 (7) | 0.053 (6) | 0.008 (5) | 0.017 (5) | 0.012 (5) |
C25' | 0.067 (7) | 0.046 (6) | 0.033 (5) | 0.007 (5) | 0.011 (5) | −0.007 (4) |
C26' | 0.054 (6) | 0.039 (5) | 0.044 (6) | −0.006 (5) | −0.002 (5) | 0.000 (5) |
C27' | 0.048 (6) | 0.029 (4) | 0.034 (5) | −0.013 (4) | 0.011 (4) | 0.004 (4) |
C28' | 0.049 (6) | 0.026 (5) | 0.037 (5) | 0.004 (5) | 0.010 (5) | 0.003 (4) |
C29' | 0.052 (6) | 0.035 (5) | 0.044 (6) | −0.005 (4) | 0.011 (5) | 0.014 (4) |
C30' | 0.070 (7) | 0.023 (5) | 0.039 (6) | −0.010 (5) | 0.016 (5) | −0.007 (4) |
C31' | 0.053 (6) | 0.035 (5) | 0.042 (6) | −0.006 (4) | 0.017 (5) | −0.013 (4) |
C32' | 0.050 (6) | 0.028 (5) | 0.053 (6) | −0.010 (4) | 0.019 (5) | −0.010 (4) |
C33' | 0.056 (7) | 0.024 (5) | 0.061 (7) | −0.003 (4) | 0.020 (5) | −0.003 (4) |
C34' | 0.062 (7) | 0.026 (5) | 0.042 (6) | −0.004 (4) | 0.008 (5) | −0.001 (4) |
C35' | 0.054 (6) | 0.038 (5) | 0.051 (6) | −0.008 (5) | 0.001 (5) | −0.006 (5) |
C36' | 0.081 (9) | 0.057 (7) | 0.054 (7) | −0.007 (7) | 0.005 (6) | −0.010 (6) |
C37' | 0.110 (9) | 0.060 (7) | 0.036 (6) | −0.034 (6) | −0.017 (6) | 0.007 (5) |
C39' | 0.047 (6) | 0.046 (6) | 0.060 (7) | 0.009 (5) | 0.015 (5) | 0.017 (5) |
C40' | 0.044 (6) | 0.087 (8) | 0.055 (7) | −0.010 (6) | 0.011 (5) | −0.010 (7) |
C41' | 0.057 (8) | 0.049 (7) | 0.125 (12) | −0.005 (6) | 0.014 (8) | −0.018 (8) |
C42' | 0.081 (9) | 0.066 (9) | 0.112 (12) | −0.010 (7) | −0.006 (9) | 0.037 (9) |
C43' | 0.087 (9) | 0.148 (12) | 0.049 (8) | −0.039 (9) | −0.001 (7) | 0.031 (9) |
C44' | 0.075 (8) | 0.064 (7) | 0.080 (8) | −0.010 (6) | 0.041 (7) | −0.012 (7) |
C45' | 0.064 (7) | 0.015 (5) | 0.054 (6) | −0.003 (5) | 0.007 (5) | −0.004 (4) |
C46' | 0.041 (6) | 0.021 (4) | 0.062 (6) | 0.009 (4) | 0.008 (5) | −0.006 (4) |
C47' | 0.037 (6) | 0.032 (5) | 0.041 (5) | −0.004 (4) | 0.006 (4) | −0.003 (4) |
C48' | 0.046 (6) | 0.037 (5) | 0.046 (6) | −0.003 (5) | 0.016 (5) | 0.011 (5) |
C49' | 0.043 (6) | 0.033 (5) | 0.066 (7) | −0.004 (5) | 0.011 (5) | 0.006 (5) |
C50' | 0.045 (7) | 0.052 (6) | 0.064 (7) | 0.012 (5) | 0.012 (5) | 0.020 (5) |
C51' | 0.047 (6) | 0.057 (7) | 0.059 (7) | 0.006 (5) | 0.001 (5) | 0.017 (6) |
C52' | 0.055 (7) | 0.049 (6) | 0.042 (6) | 0.000 (5) | −0.003 (5) | 0.012 (5) |
C53' | 0.059 (7) | 0.033 (5) | 0.039 (6) | −0.010 (5) | 0.014 (5) | 0.009 (4) |
C54' | 0.052 (6) | 0.039 (6) | 0.048 (6) | −0.004 (5) | 0.018 (5) | 0.003 (5) |
C55' | 0.064 (7) | 0.039 (5) | 0.048 (6) | −0.003 (5) | 0.020 (5) | −0.003 (5) |
C56' | 0.071 (8) | 0.045 (6) | 0.047 (6) | −0.004 (6) | 0.015 (6) | −0.009 (5) |
C57' | 0.074 (8) | 0.041 (6) | 0.066 (7) | 0.010 (5) | 0.041 (6) | 0.000 (5) |
C58' | 0.061 (7) | 0.035 (5) | 0.046 (6) | −0.001 (5) | 0.016 (5) | 0.001 (4) |
C59' | 0.042 (6) | 0.034 (5) | 0.037 (5) | −0.005 (4) | 0.004 (4) | 0.004 (4) |
Cl1—C29 | 1.774 (8) | O1'—C6' | 1.417 (9) |
O1—C1 | 1.395 (8) | O2'—C13' | 1.351 (9) |
O1—C6 | 1.404 (9) | O2'—C2' | 1.450 (8) |
O2—C13 | 1.354 (9) | O3'—C3' | 1.434 (9) |
O2—C2 | 1.444 (8) | O3'—C20' | 1.447 (8) |
O3—C3 | 1.428 (9) | O4'—C30' | 1.409 (9) |
O3—C20 | 1.450 (9) | O4'—C4' | 1.439 (8) |
O4—C30 | 1.406 (9) | O5'—C5' | 1.422 (8) |
O4—C4 | 1.435 (8) | O5'—C1' | 1.434 (9) |
O5—C1 | 1.418 (9) | O6'—C13' | 1.205 (9) |
O5—C5 | 1.429 (8) | O7'—C9' | 1.382 (9) |
O6—C13 | 1.199 (9) | O7'—C12' | 1.420 (9) |
O7—C9 | 1.376 (9) | O8'—C28' | 1.353 (9) |
O7—C12 | 1.419 (10) | O8'—C27' | 1.460 (8) |
O8—C28 | 1.358 (9) | O9'—C28' | 1.208 (9) |
O8—C27 | 1.461 (9) | O10'—C30' | 1.414 (9) |
O9—C28 | 1.208 (9) | O10'—C31' | 1.446 (9) |
O10—C30 | 1.411 (9) | O11'—C36' | 1.330 (12) |
O10—C31 | 1.450 (9) | O11'—C35' | 1.443 (9) |
O11—C36 | 1.340 (11) | O12'—C36' | 1.207 (12) |
O11—C35 | 1.443 (9) | O13'—C38A | 1.432 (15) |
O12—C36 | 1.196 (11) | O13'—C33' | 1.437 (9) |
O13—C38 | 1.384 (8) | O13'—C38B | 1.506 (18) |
O13—C33 | 1.432 (9) | O14'—C45' | 1.352 (9) |
O14—C45 | 1.344 (9) | O14'—C32' | 1.458 (9) |
O14—C32 | 1.452 (9) | O15'—C45' | 1.183 (9) |
O15—C45 | 1.195 (9) | O16'—C45' | 1.333 (10) |
O16—C45 | 1.318 (10) | O16'—C46' | 1.460 (8) |
O16—C46 | 1.463 (8) | N1'—N2' | 1.214 (12) |
N1—N2 | 1.248 (10) | N1'—C34' | 1.476 (10) |
N1—C34 | 1.468 (10) | N2'—N3' | 1.218 (12) |
N2—N3 | 1.146 (10) | C1'—C2' | 1.523 (10) |
C1—C2 | 1.516 (10) | C1'—H1' | 1.0000 |
C1—H1 | 1.0000 | C2'—C3' | 1.521 (10) |
C2—C3 | 1.520 (10) | C2'—H2' | 1.0000 |
C2—H2 | 1.0000 | C3'—C4' | 1.513 (10) |
C3—C4 | 1.529 (10) | C3'—H3' | 1.0000 |
C3—H3 | 1.0000 | C4'—C5' | 1.530 (10) |
C4—C5 | 1.511 (10) | C4'—H4' | 1.0000 |
C4—H4 | 1.0000 | C5'—C27' | 1.512 (10) |
C5—C27 | 1.516 (10) | C5'—H5' | 1.0000 |
C5—H5 | 1.0000 | C6'—C11' | 1.358 (10) |
C6—C11 | 1.369 (11) | C6'—C7' | 1.385 (10) |
C6—C7 | 1.376 (11) | C7'—C8' | 1.377 (10) |
C7—C8 | 1.388 (11) | C7'—H7' | 0.9500 |
C7—H7 | 0.9500 | C8'—C9' | 1.386 (11) |
C8—C9 | 1.378 (11) | C8'—H8' | 0.9500 |
C8—H8 | 0.9500 | C9'—C10' | 1.377 (11) |
C9—C10 | 1.367 (11) | C10'—C11' | 1.403 (10) |
C10—C11 | 1.400 (11) | C10'—H10' | 0.9500 |
C10—H10 | 0.9500 | C12'—H12D | 0.9800 |
C11—H11 | 0.9500 | C12'—H12E | 0.9800 |
C12—H12A | 0.9800 | C12'—H12F | 0.9800 |
C12—H12B | 0.9800 | C11'—H11' | 0.9500 |
C12—H12C | 0.9800 | C13'—C14' | 1.490 (11) |
C13—C14 | 1.491 (11) | C14'—C19' | 1.376 (11) |
C14—C19 | 1.388 (11) | C14'—C15' | 1.399 (11) |
C14—C15 | 1.410 (11) | C15'—C16' | 1.374 (11) |
C15—C16 | 1.362 (11) | C15'—H15' | 0.9500 |
C15—H15 | 0.9500 | C16'—C17' | 1.389 (12) |
C16—C17 | 1.370 (12) | C16'—H16' | 0.9500 |
C16—H16 | 0.9500 | C17'—C18' | 1.381 (11) |
C17—C18 | 1.380 (11) | C17'—H17' | 0.9500 |
C17—H17 | 0.9500 | C18'—C19' | 1.413 (11) |
C18—C19 | 1.387 (11) | C18'—H18' | 0.9500 |
C18—H18 | 0.9500 | C19'—H19' | 0.9500 |
C19—H19 | 0.9500 | C20'—C21' | 1.506 (11) |
C20—C21 | 1.519 (11) | C20'—H20C | 0.9900 |
C20—H20A | 0.9900 | C20'—H20D | 0.9900 |
C20—H20B | 0.9900 | C21'—C22' | 1.361 (10) |
C21—C22 | 1.390 (11) | C21'—C26' | 1.392 (11) |
C21—C26 | 1.396 (12) | C22'—C23' | 1.397 (11) |
C22—C23 | 1.389 (12) | C22'—H22' | 0.9500 |
C22—H22 | 0.9500 | C23'—C24' | 1.359 (11) |
C23—C24 | 1.384 (13) | C23'—H23' | 0.9500 |
C23—H23 | 0.9500 | C24'—C25' | 1.389 (11) |
C24—C25 | 1.364 (13) | C24'—H24' | 0.9500 |
C24—H24 | 0.9500 | C25'—C26' | 1.383 (11) |
C25—C26 | 1.393 (12) | C25'—H25' | 0.9500 |
C25—H25 | 0.9500 | C26'—H26' | 0.9500 |
C26—H26 | 0.9500 | C27'—H27C | 0.9900 |
C27—H27A | 0.9900 | C27'—H27D | 0.9900 |
C27—H27B | 0.9900 | C28'—C29' | 1.492 (11) |
C28—C29 | 1.490 (11) | C29'—H29C | 0.9900 |
C29—H29A | 0.9900 | C29'—H29D | 0.9900 |
C29—H29B | 0.9900 | C30'—C34' | 1.522 (10) |
C30—C34 | 1.532 (10) | C30'—H30' | 1.0000 |
C30—H30 | 1.0000 | C31'—C35' | 1.514 (11) |
C31—C35 | 1.523 (10) | C31'—C32' | 1.531 (11) |
C31—C32 | 1.532 (11) | C31'—H31' | 1.0000 |
C31—H31 | 1.0000 | C32'—C33' | 1.509 (11) |
C32—C33 | 1.519 (11) | C32'—H32' | 1.0000 |
C32—H32 | 1.0000 | C33'—C34' | 1.494 (11) |
C33—C34 | 1.514 (11) | C33'—H33' | 1.0000 |
C33—H33 | 1.0000 | C34'—H34' | 1.0000 |
C34—H34 | 1.0000 | C35'—H35C | 0.9900 |
C35—H35A | 0.9900 | C35'—H35D | 0.9900 |
C35—H35B | 0.9900 | C36'—C37' | 1.503 (13) |
C36—C37 | 1.507 (13) | C37'—H37D | 0.9800 |
C37—H37A | 0.9800 | C37'—H37E | 0.9800 |
C37—H37B | 0.9800 | C37'—H37F | 0.9800 |
C37—H37C | 0.9800 | C39'—C44' | 1.357 (12) |
C38—C39 | 1.531 (11) | C39'—C40' | 1.389 (12) |
C38—H38A | 0.9900 | C39'—C38A | 1.533 (16) |
C38—H38B | 0.9900 | C39'—C38B | 1.534 (17) |
C39—C40 | 1.353 (12) | C40'—C41' | 1.378 (13) |
C39—C44 | 1.380 (11) | C40'—H40' | 0.9500 |
C40—C41 | 1.376 (12) | C41'—C42' | 1.321 (15) |
C40—H40 | 0.9500 | C41'—H41' | 0.9500 |
C41—C42 | 1.365 (13) | C42'—C43' | 1.365 (16) |
C41—H41 | 0.9500 | C42'—H42' | 0.9500 |
C42—C43 | 1.381 (13) | C43'—C44' | 1.384 (13) |
C42—H42 | 0.9500 | C43'—H43' | 0.9500 |
C43—C44 | 1.393 (11) | C44'—H44' | 0.9500 |
C43—H43 | 0.9500 | C46'—C47' | 1.509 (11) |
C44—H44 | 0.9500 | C46'—H46C | 0.9900 |
C46—C47 | 1.493 (11) | C46'—H46D | 0.9900 |
C46—H46A | 0.9900 | C47'—C48' | 1.519 (11) |
C46—H46B | 0.9900 | C47'—C59' | 1.526 (10) |
C47—C48 | 1.528 (11) | C47'—H47' | 1.0000 |
C47—C59 | 1.528 (11) | C48'—C49' | 1.363 (11) |
C47—H47 | 1.0000 | C48'—C53' | 1.404 (11) |
C48—C49 | 1.368 (11) | C49'—C50' | 1.413 (12) |
C48—C53 | 1.407 (11) | C49'—H49' | 0.9500 |
C49—C50 | 1.397 (12) | C50'—C51' | 1.387 (12) |
C49—H49 | 0.9500 | C50'—H50' | 0.9500 |
C50—C51 | 1.386 (13) | C51'—C52' | 1.365 (12) |
C50—H50 | 0.9500 | C51'—H51' | 0.9500 |
C51—C52 | 1.383 (13) | C52'—C53' | 1.388 (12) |
C51—H51 | 0.9500 | C52'—H52' | 0.9500 |
C52—C53 | 1.397 (12) | C53'—C54' | 1.464 (11) |
C52—H52 | 0.9500 | C54'—C55' | 1.402 (12) |
C53—C54 | 1.455 (12) | C54'—C59' | 1.412 (11) |
C54—C59 | 1.396 (11) | C55'—C56' | 1.376 (12) |
C54—C55 | 1.403 (12) | C55'—H55' | 0.9500 |
C55—C56 | 1.355 (12) | C56'—C57' | 1.394 (12) |
C55—H55 | 0.9500 | C56'—H56' | 0.9500 |
C56—C57 | 1.387 (12) | C57'—C58' | 1.403 (11) |
C56—H56 | 0.9500 | C57'—H57' | 0.9500 |
C57—C58 | 1.407 (12) | C58'—C59' | 1.375 (11) |
C57—H57 | 0.9500 | C58'—H58' | 0.9500 |
C58—C59 | 1.371 (11) | C38A—H38C | 1.07 (3) |
C58—H58 | 0.9500 | C38A—H38D | 0.93 (3) |
Cl1'—C29' | 1.781 (7) | C38B—H38E | 1.05 (2) |
O1'—C1' | 1.395 (8) | C38B—H38F | 1.12 (3) |
C1—O1—C6 | 113.6 (6) | C9'—O7'—C12' | 116.7 (6) |
C13—O2—C2 | 120.0 (6) | C28'—O8'—C27' | 117.6 (6) |
C3—O3—C20 | 110.8 (6) | C30'—O10'—C31' | 115.8 (6) |
C30—O4—C4 | 114.3 (6) | C36'—O11'—C35' | 116.3 (8) |
C1—O5—C5 | 112.1 (5) | C38A—O13'—C33' | 118.8 (9) |
C9—O7—C12 | 117.1 (6) | C33'—O13'—C38B | 109.0 (8) |
C28—O8—C27 | 118.0 (7) | C45'—O14'—C32' | 117.0 (7) |
C30—O10—C31 | 114.6 (6) | C45'—O16'—C46' | 116.2 (6) |
C36—O11—C35 | 116.3 (7) | N2'—N1'—C34' | 107.8 (8) |
C38—O13—C33 | 117.5 (6) | N3'—N2'—N1' | 171.3 (12) |
C45—O14—C32 | 116.4 (6) | O1'—C1'—O5' | 107.6 (6) |
C45—O16—C46 | 116.9 (6) | O1'—C1'—C2' | 107.3 (6) |
N2—N1—C34 | 113.7 (7) | O5'—C1'—C2' | 109.9 (6) |
N3—N2—N1 | 171.6 (10) | O1'—C1'—H1' | 110.6 |
O1—C1—O5 | 108.0 (6) | O5'—C1'—H1' | 110.6 |
O1—C1—C2 | 107.5 (6) | C2'—C1'—H1' | 110.6 |
O5—C1—C2 | 109.9 (6) | O2'—C2'—C3' | 107.5 (6) |
O1—C1—H1 | 110.4 | O2'—C2'—C1' | 106.3 (6) |
O5—C1—H1 | 110.4 | C3'—C2'—C1' | 114.0 (6) |
C2—C1—H1 | 110.4 | O2'—C2'—H2' | 109.6 |
O2—C2—C1 | 106.7 (6) | C3'—C2'—H2' | 109.6 |
O2—C2—C3 | 107.1 (6) | C1'—C2'—H2' | 109.6 |
C1—C2—C3 | 113.4 (6) | O3'—C3'—C4' | 113.9 (6) |
O2—C2—H2 | 109.9 | O3'—C3'—C2' | 107.7 (6) |
C1—C2—H2 | 109.9 | C4'—C3'—C2' | 110.7 (6) |
C3—C2—H2 | 109.9 | O3'—C3'—H3' | 108.1 |
O3—C3—C2 | 108.9 (6) | C4'—C3'—H3' | 108.1 |
O3—C3—C4 | 112.1 (6) | C2'—C3'—H3' | 108.1 |
C2—C3—C4 | 110.6 (6) | O4'—C4'—C3' | 110.8 (6) |
O3—C3—H3 | 108.4 | O4'—C4'—C5' | 110.5 (6) |
C2—C3—H3 | 108.4 | C3'—C4'—C5' | 105.9 (6) |
C4—C3—H3 | 108.4 | O4'—C4'—H4' | 109.8 |
O4—C4—C5 | 108.5 (6) | C3'—C4'—H4' | 109.8 |
O4—C4—C3 | 110.9 (6) | C5'—C4'—H4' | 109.8 |
C5—C4—C3 | 106.2 (6) | O5'—C5'—C27' | 106.8 (6) |
O4—C4—H4 | 110.4 | O5'—C5'—C4' | 107.5 (6) |
C5—C4—H4 | 110.4 | C27'—C5'—C4' | 116.6 (6) |
C3—C4—H4 | 110.4 | O5'—C5'—H5' | 108.6 |
O5—C5—C4 | 108.4 (6) | C27'—C5'—H5' | 108.6 |
O5—C5—C27 | 106.9 (6) | C4'—C5'—H5' | 108.6 |
C4—C5—C27 | 116.6 (6) | C11'—C6'—C7' | 121.5 (8) |
O5—C5—H5 | 108.2 | C11'—C6'—O1' | 121.9 (7) |
C4—C5—H5 | 108.2 | C7'—C6'—O1' | 116.6 (7) |
C27—C5—H5 | 108.2 | C8'—C7'—C6' | 118.7 (8) |
C11—C6—C7 | 119.7 (8) | C8'—C7'—H7' | 120.6 |
C11—C6—O1 | 122.8 (7) | C6'—C7'—H7' | 120.6 |
C7—C6—O1 | 117.4 (8) | C7'—C8'—C9' | 120.1 (8) |
C6—C7—C8 | 119.7 (8) | C7'—C8'—H8' | 119.9 |
C6—C7—H7 | 120.1 | C9'—C8'—H8' | 119.9 |
C8—C7—H7 | 120.1 | C10'—C9'—O7' | 123.8 (8) |
C9—C8—C7 | 120.0 (8) | C10'—C9'—C8' | 121.2 (8) |
C9—C8—H8 | 120.0 | O7'—C9'—C8' | 115.1 (7) |
C7—C8—H8 | 120.0 | C9'—C10'—C11' | 118.2 (8) |
C10—C9—C8 | 120.7 (8) | C9'—C10'—H10' | 120.9 |
C10—C9—O7 | 124.4 (8) | C11'—C10'—H10' | 120.9 |
C8—C9—O7 | 114.9 (8) | O7'—C12'—H12D | 109.5 |
C9—C10—C11 | 118.7 (8) | O7'—C12'—H12E | 109.5 |
C9—C10—H10 | 120.6 | H12D—C12'—H12E | 109.5 |
C11—C10—H10 | 120.6 | O7'—C12'—H12F | 109.5 |
C6—C11—C10 | 121.0 (8) | H12D—C12'—H12F | 109.5 |
C6—C11—H11 | 119.5 | H12E—C12'—H12F | 109.5 |
C10—C11—H11 | 119.5 | C6'—C11'—C10' | 120.3 (8) |
O7—C12—H12A | 109.5 | C6'—C11'—H11' | 119.9 |
O7—C12—H12B | 109.5 | C10'—C11'—H11' | 119.9 |
H12A—C12—H12B | 109.5 | O6'—C13'—O2' | 123.6 (8) |
O7—C12—H12C | 109.5 | O6'—C13'—C14' | 124.5 (8) |
H12A—C12—H12C | 109.5 | O2'—C13'—C14' | 112.0 (8) |
H12B—C12—H12C | 109.5 | C19'—C14'—C15' | 120.6 (8) |
O6—C13—O2 | 123.0 (8) | C19'—C14'—C13' | 117.5 (8) |
O6—C13—C14 | 125.2 (8) | C15'—C14'—C13' | 121.9 (8) |
O2—C13—C14 | 111.7 (8) | C16'—C15'—C14' | 119.3 (8) |
C19—C14—C15 | 119.4 (8) | C16'—C15'—H15' | 120.4 |
C19—C14—C13 | 117.7 (8) | C14'—C15'—H15' | 120.4 |
C15—C14—C13 | 122.8 (8) | C15'—C16'—C17' | 121.2 (9) |
C16—C15—C14 | 119.5 (8) | C15'—C16'—H16' | 119.4 |
C16—C15—H15 | 120.3 | C17'—C16'—H16' | 119.4 |
C14—C15—H15 | 120.3 | C18'—C17'—C16' | 119.6 (9) |
C15—C16—C17 | 121.2 (9) | C18'—C17'—H17' | 120.2 |
C15—C16—H16 | 119.4 | C16'—C17'—H17' | 120.2 |
C17—C16—H16 | 119.4 | C17'—C18'—C19' | 119.8 (9) |
C16—C17—C18 | 119.9 (9) | C17'—C18'—H18' | 120.1 |
C16—C17—H17 | 120.0 | C19'—C18'—H18' | 120.1 |
C18—C17—H17 | 120.0 | C14'—C19'—C18' | 119.5 (9) |
C17—C18—C19 | 120.2 (9) | C14'—C19'—H19' | 120.3 |
C17—C18—H18 | 119.9 | C18'—C19'—H19' | 120.3 |
C19—C18—H18 | 119.9 | O3'—C20'—C21' | 111.5 (7) |
C14—C19—C18 | 119.6 (9) | O3'—C20'—H20C | 109.3 |
C14—C19—H19 | 120.2 | C21'—C20'—H20C | 109.3 |
C18—C19—H19 | 120.2 | O3'—C20'—H20D | 109.3 |
O3—C20—C21 | 110.4 (7) | C21'—C20'—H20D | 109.3 |
O3—C20—H20A | 109.6 | H20C—C20'—H20D | 108.0 |
C21—C20—H20A | 109.6 | C22'—C21'—C26' | 118.3 (8) |
O3—C20—H20B | 109.6 | C22'—C21'—C20' | 121.6 (8) |
C21—C20—H20B | 109.6 | C26'—C21'—C20' | 119.8 (8) |
H20A—C20—H20B | 108.1 | C21'—C22'—C23' | 121.7 (8) |
C22—C21—C26 | 118.8 (9) | C21'—C22'—H22' | 119.2 |
C22—C21—C20 | 121.9 (8) | C23'—C22'—H22' | 119.2 |
C26—C21—C20 | 119.2 (9) | C24'—C23'—C22' | 119.4 (8) |
C21—C22—C23 | 119.2 (9) | C24'—C23'—H23' | 120.3 |
C21—C22—H22 | 120.4 | C22'—C23'—H23' | 120.3 |
C23—C22—H22 | 120.4 | C23'—C24'—C25' | 120.3 (9) |
C24—C23—C22 | 121.5 (10) | C23'—C24'—H24' | 119.8 |
C24—C23—H23 | 119.2 | C25'—C24'—H24' | 119.8 |
C22—C23—H23 | 119.2 | C26'—C25'—C24' | 119.5 (8) |
C25—C24—C23 | 119.6 (10) | C26'—C25'—H25' | 120.3 |
C25—C24—H24 | 120.2 | C24'—C25'—H25' | 120.3 |
C23—C24—H24 | 120.2 | C25'—C26'—C21' | 120.8 (8) |
C24—C25—C26 | 119.7 (10) | C25'—C26'—H26' | 119.6 |
C24—C25—H25 | 120.1 | C21'—C26'—H26' | 119.6 |
C26—C25—H25 | 120.1 | O8'—C27'—C5' | 106.6 (6) |
C25—C26—C21 | 121.1 (9) | O8'—C27'—H27C | 110.4 |
C25—C26—H26 | 119.5 | C5'—C27'—H27C | 110.4 |
C21—C26—H26 | 119.5 | O8'—C27'—H27D | 110.4 |
O8—C27—C5 | 107.8 (6) | C5'—C27'—H27D | 110.4 |
O8—C27—H27A | 110.1 | H27C—C27'—H27D | 108.6 |
C5—C27—H27A | 110.1 | O9'—C28'—O8' | 124.1 (8) |
O8—C27—H27B | 110.1 | O9'—C28'—C29' | 127.3 (8) |
C5—C27—H27B | 110.1 | O8'—C28'—C29' | 108.6 (7) |
H27A—C27—H27B | 108.5 | C28'—C29'—Cl1' | 111.4 (6) |
O9—C28—O8 | 123.7 (8) | C28'—C29'—H29C | 109.3 |
O9—C28—C29 | 128.2 (8) | Cl1'—C29'—H29C | 109.3 |
O8—C28—C29 | 108.1 (8) | C28'—C29'—H29D | 109.3 |
C28—C29—Cl1 | 111.2 (6) | Cl1'—C29'—H29D | 109.4 |
C28—C29—H29A | 109.4 | H29C—C29'—H29D | 108.0 |
Cl1—C29—H29A | 109.4 | O10'—C30'—O4' | 112.6 (6) |
C28—C29—H29B | 109.4 | O10'—C30'—C34' | 108.5 (6) |
Cl1—C29—H29B | 109.4 | O4'—C30'—C34' | 108.9 (7) |
H29A—C29—H29B | 108.0 | O10'—C30'—H30' | 108.9 |
O4—C30—O10 | 112.7 (6) | O4'—C30'—H30' | 108.9 |
O4—C30—C34 | 107.8 (7) | C34'—C30'—H30' | 108.9 |
O10—C30—C34 | 110.3 (6) | O10'—C31'—C35' | 107.1 (7) |
O4—C30—H30 | 108.6 | O10'—C31'—C32' | 109.6 (7) |
O10—C30—H30 | 108.6 | C35'—C31'—C32' | 112.0 (7) |
C34—C30—H30 | 108.6 | O10'—C31'—H31' | 109.4 |
O10—C31—C35 | 106.9 (7) | C35'—C31'—H31' | 109.4 |
O10—C31—C32 | 108.3 (6) | C32'—C31'—H31' | 109.4 |
C35—C31—C32 | 113.2 (7) | O14'—C32'—C33' | 107.1 (7) |
O10—C31—H31 | 109.5 | O14'—C32'—C31' | 105.9 (6) |
C35—C31—H31 | 109.5 | C33'—C32'—C31' | 111.3 (6) |
C32—C31—H31 | 109.5 | O14'—C32'—H32' | 110.8 |
O14—C32—C33 | 107.6 (7) | C33'—C32'—H32' | 110.8 |
O14—C32—C31 | 105.9 (6) | C31'—C32'—H32' | 110.8 |
C33—C32—C31 | 109.8 (6) | O13'—C33'—C34' | 108.0 (7) |
O14—C32—H32 | 111.1 | O13'—C33'—C32' | 110.3 (6) |
C33—C32—H32 | 111.1 | C34'—C33'—C32' | 109.4 (7) |
C31—C32—H32 | 111.1 | O13'—C33'—H33' | 109.7 |
O13—C33—C34 | 114.3 (7) | C34'—C33'—H33' | 109.7 |
O13—C33—C32 | 113.3 (6) | C32'—C33'—H33' | 109.7 |
C34—C33—C32 | 110.1 (7) | N1'—C34'—C33' | 111.6 (7) |
O13—C33—H33 | 106.1 | N1'—C34'—C30' | 107.0 (6) |
C34—C33—H33 | 106.1 | C33'—C34'—C30' | 110.9 (7) |
C32—C33—H33 | 106.1 | N1'—C34'—H34' | 109.1 |
N1—C34—C33 | 112.7 (7) | C33'—C34'—H34' | 109.1 |
N1—C34—C30 | 106.9 (7) | C30'—C34'—H34' | 109.1 |
C33—C34—C30 | 108.8 (7) | O11'—C35'—C31' | 110.0 (6) |
N1—C34—H34 | 109.5 | O11'—C35'—H35C | 109.7 |
C33—C34—H34 | 109.5 | C31'—C35'—H35C | 109.7 |
C30—C34—H34 | 109.5 | O11'—C35'—H35D | 109.7 |
O11—C35—C31 | 109.0 (6) | C31'—C35'—H35D | 109.7 |
O11—C35—H35A | 109.9 | H35C—C35'—H35D | 108.2 |
C31—C35—H35A | 109.9 | O12'—C36'—O11' | 123.2 (10) |
O11—C35—H35B | 109.9 | O12'—C36'—C37' | 124.4 (11) |
C31—C35—H35B | 109.9 | O11'—C36'—C37' | 112.3 (10) |
H35A—C35—H35B | 108.3 | C36'—C37'—H37D | 109.5 |
O12—C36—O11 | 121.9 (10) | C36'—C37'—H37E | 109.5 |
O12—C36—C37 | 124.8 (11) | H37D—C37'—H37E | 109.5 |
O11—C36—C37 | 113.2 (10) | C36'—C37'—H37F | 109.5 |
C36—C37—H37A | 109.5 | H37D—C37'—H37F | 109.5 |
C36—C37—H37B | 109.5 | H37E—C37'—H37F | 109.5 |
H37A—C37—H37B | 109.5 | C44'—C39'—C40' | 118.3 (9) |
C36—C37—H37C | 109.5 | C44'—C39'—C38A | 131.3 (14) |
H37A—C37—H37C | 109.5 | C40'—C39'—C38A | 110.2 (14) |
H37B—C37—H37C | 109.5 | C44'—C39'—C38B | 105.1 (15) |
O13—C38—C39 | 110.5 (7) | C40'—C39'—C38B | 136.5 (15) |
O13—C38—H38A | 109.6 | C41'—C40'—C39' | 119.9 (9) |
C39—C38—H38A | 109.6 | C41'—C40'—H40' | 120.1 |
O13—C38—H38B | 109.6 | C39'—C40'—H40' | 120.1 |
C39—C38—H38B | 109.6 | C42'—C41'—C40' | 122.2 (11) |
H38A—C38—H38B | 108.1 | C42'—C41'—H41' | 118.9 |
C40—C39—C44 | 120.0 (9) | C40'—C41'—H41' | 118.9 |
C40—C39—C38 | 121.5 (8) | C41'—C42'—C43' | 118.1 (12) |
C44—C39—C38 | 118.5 (8) | C41'—C42'—H42' | 121.0 |
C39—C40—C41 | 119.2 (9) | C43'—C42'—H42' | 121.0 |
C39—C40—H40 | 120.4 | C42'—C43'—C44' | 122.0 (11) |
C41—C40—H40 | 120.4 | C42'—C43'—H43' | 119.0 |
C42—C41—C40 | 122.8 (10) | C44'—C43'—H43' | 119.0 |
C42—C41—H41 | 118.6 | C39'—C44'—C43' | 119.5 (10) |
C40—C41—H41 | 118.6 | C39'—C44'—H44' | 120.3 |
C41—C42—C43 | 117.9 (10) | C43'—C44'—H44' | 120.3 |
C41—C42—H42 | 121.1 | O15'—C45'—O16' | 128.0 (8) |
C43—C42—H42 | 121.1 | O15'—C45'—O14' | 125.9 (9) |
C42—C43—C44 | 120.0 (9) | O16'—C45'—O14' | 106.2 (8) |
C42—C43—H43 | 120.0 | O16'—C46'—C47' | 109.0 (6) |
C44—C43—H43 | 120.0 | O16'—C46'—H46C | 109.9 |
C39—C44—C43 | 120.1 (9) | C47'—C46'—H46C | 109.9 |
C39—C44—H44 | 119.9 | O16'—C46'—H46D | 109.9 |
C43—C44—H44 | 119.9 | C47'—C46'—H46D | 109.9 |
O15—C45—O16 | 128.0 (8) | H46C—C46'—H46D | 108.3 |
O15—C45—O14 | 125.4 (9) | C46'—C47'—C48' | 113.4 (7) |
O16—C45—O14 | 106.5 (7) | C46'—C47'—C59' | 108.7 (6) |
O16—C46—C47 | 108.2 (6) | C48'—C47'—C59' | 102.4 (7) |
O16—C46—H46A | 110.1 | C46'—C47'—H47' | 110.7 |
C47—C46—H46A | 110.1 | C48'—C47'—H47' | 110.7 |
O16—C46—H46B | 110.1 | C59'—C47'—H47' | 110.7 |
C47—C46—H46B | 110.1 | C49'—C48'—C53' | 121.2 (9) |
H46A—C46—H46B | 108.4 | C49'—C48'—C47' | 128.8 (8) |
C46—C47—C48 | 114.3 (7) | C53'—C48'—C47' | 110.0 (7) |
C46—C47—C59 | 110.3 (6) | C48'—C49'—C50' | 118.7 (9) |
C48—C47—C59 | 102.2 (7) | C48'—C49'—H49' | 120.7 |
C46—C47—H47 | 109.9 | C50'—C49'—H49' | 120.7 |
C48—C47—H47 | 109.9 | C51'—C50'—C49' | 119.2 (9) |
C59—C47—H47 | 109.9 | C51'—C50'—H50' | 120.4 |
C49—C48—C53 | 121.0 (9) | C49'—C50'—H50' | 120.4 |
C49—C48—C47 | 129.5 (8) | C52'—C51'—C50' | 122.2 (9) |
C53—C48—C47 | 109.4 (7) | C52'—C51'—H51' | 118.9 |
C48—C49—C50 | 118.7 (9) | C50'—C51'—H51' | 118.9 |
C48—C49—H49 | 120.6 | C51'—C52'—C53' | 118.6 (9) |
C50—C49—H49 | 120.6 | C51'—C52'—H52' | 120.7 |
C51—C50—C49 | 120.7 (9) | C53'—C52'—H52' | 120.7 |
C51—C50—H50 | 119.6 | C52'—C53'—C48' | 120.1 (8) |
C49—C50—H50 | 119.6 | C52'—C53'—C54' | 131.0 (9) |
C52—C51—C50 | 120.9 (9) | C48'—C53'—C54' | 109.0 (8) |
C52—C51—H51 | 119.6 | C55'—C54'—C59' | 119.3 (9) |
C50—C51—H51 | 119.6 | C55'—C54'—C53' | 131.9 (9) |
C51—C52—C53 | 118.7 (10) | C59'—C54'—C53' | 108.7 (8) |
C51—C52—H52 | 120.7 | C56'—C55'—C54' | 119.9 (9) |
C53—C52—H52 | 120.7 | C56'—C55'—H55' | 120.0 |
C52—C53—C48 | 119.9 (9) | C54'—C55'—H55' | 120.0 |
C52—C53—C54 | 131.0 (9) | C55'—C56'—C57' | 120.4 (9) |
C48—C53—C54 | 109.1 (8) | C55'—C56'—H56' | 119.8 |
C59—C54—C55 | 119.6 (9) | C57'—C56'—H56' | 119.8 |
C59—C54—C53 | 109.4 (8) | C56'—C57'—C58' | 120.5 (9) |
C55—C54—C53 | 131.1 (9) | C56'—C57'—H57' | 119.8 |
C56—C55—C54 | 119.8 (10) | C58'—C57'—H57' | 119.8 |
C56—C55—H55 | 120.1 | C59'—C58'—C57' | 119.1 (9) |
C54—C55—H55 | 120.1 | C59'—C58'—H58' | 120.4 |
C55—C56—C57 | 120.1 (9) | C57'—C58'—H58' | 120.4 |
C55—C56—H56 | 119.9 | C58'—C59'—C54' | 120.7 (8) |
C57—C56—H56 | 119.9 | C58'—C59'—C47' | 129.7 (8) |
C56—C57—C58 | 121.6 (9) | C54'—C59'—C47' | 109.5 (7) |
C56—C57—H57 | 119.2 | O13'—C38A—C39' | 108.0 (11) |
C58—C57—H57 | 119.2 | O13'—C38A—H38C | 105.0 (17) |
C59—C58—C57 | 117.5 (9) | C39'—C38A—H38C | 106.4 (18) |
C59—C58—H58 | 121.3 | O13'—C38A—H38D | 114.2 (19) |
C57—C58—H58 | 121.3 | C39'—C38A—H38D | 115.6 (18) |
C58—C59—C54 | 121.4 (8) | H38C—C38A—H38D | 106.8 (15) |
C58—C59—C47 | 128.8 (8) | O13'—C38B—C39' | 104.2 (12) |
C54—C59—C47 | 109.8 (7) | O13'—C38B—H38E | 117 (2) |
C1'—O1'—C6' | 114.0 (6) | C39'—C38B—H38E | 114.8 (17) |
C13'—O2'—C2' | 119.8 (6) | O13'—C38B—H38F | 113.1 (18) |
C3'—O3'—C20' | 111.2 (6) | C39'—C38B—H38F | 110.6 (18) |
C30'—O4'—C4' | 113.0 (6) | H38E—C38B—H38F | 96.9 (16) |
C5'—O5'—C1' | 112.4 (5) | ||
C6—O1—C1—O5 | −92.1 (7) | C5'—O5'—C1'—C2' | −57.4 (8) |
C6—O1—C1—C2 | 149.3 (6) | C13'—O2'—C2'—C3' | −127.5 (7) |
C5—O5—C1—O1 | −176.0 (6) | C13'—O2'—C2'—C1' | 110.0 (7) |
C5—O5—C1—C2 | −59.0 (8) | O1'—C1'—C2'—O2' | −79.4 (7) |
C13—O2—C2—C1 | 115.1 (7) | O5'—C1'—C2'—O2' | 163.8 (5) |
C13—O2—C2—C3 | −123.2 (7) | O1'—C1'—C2'—C3' | 162.3 (6) |
O1—C1—C2—O2 | −76.6 (7) | O5'—C1'—C2'—C3' | 45.6 (9) |
O5—C1—C2—O2 | 166.0 (6) | C20'—O3'—C3'—C4' | 124.2 (7) |
O1—C1—C2—C3 | 165.7 (6) | C20'—O3'—C3'—C2' | −112.6 (7) |
O5—C1—C2—C3 | 48.4 (9) | O2'—C2'—C3'—O3' | 69.6 (7) |
C20—O3—C3—C2 | −109.5 (7) | C1'—C2'—C3'—O3' | −172.8 (6) |
C20—O3—C3—C4 | 127.8 (6) | O2'—C2'—C3'—C4' | −165.2 (6) |
O2—C2—C3—O3 | 70.6 (7) | C1'—C2'—C3'—C4' | −47.6 (9) |
C1—C2—C3—O3 | −172.0 (6) | C30'—O4'—C4'—C3' | 94.1 (7) |
O2—C2—C3—C4 | −165.8 (6) | C30'—O4'—C4'—C5' | −148.8 (6) |
C1—C2—C3—C4 | −48.4 (9) | O3'—C3'—C4'—O4' | −62.3 (8) |
C30—O4—C4—C5 | −154.8 (6) | C2'—C3'—C4'—O4' | 176.1 (6) |
C30—O4—C4—C3 | 88.9 (7) | O3'—C3'—C4'—C5' | 177.8 (6) |
O3—C3—C4—O4 | −65.5 (8) | C2'—C3'—C4'—C5' | 56.3 (8) |
C2—C3—C4—O4 | 172.7 (6) | C1'—O5'—C5'—C27' | −164.4 (6) |
O3—C3—C4—C5 | 176.8 (6) | C1'—O5'—C5'—C4' | 69.9 (8) |
C2—C3—C4—C5 | 55.0 (8) | O4'—C4'—C5'—O5' | 172.8 (5) |
C1—O5—C5—C4 | 69.5 (8) | C3'—C4'—C5'—O5' | −67.1 (7) |
C1—O5—C5—C27 | −164.1 (6) | O4'—C4'—C5'—C27' | 53.1 (9) |
O4—C4—C5—O5 | 175.7 (5) | C3'—C4'—C5'—C27' | 173.1 (7) |
C3—C4—C5—O5 | −64.9 (7) | C1'—O1'—C6'—C11' | 83.6 (9) |
O4—C4—C5—C27 | 55.1 (9) | C1'—O1'—C6'—C7' | −96.8 (8) |
C3—C4—C5—C27 | 174.5 (7) | C11'—C6'—C7'—C8' | 0.1 (12) |
C1—O1—C6—C11 | 80.3 (9) | O1'—C6'—C7'—C8' | −179.6 (7) |
C1—O1—C6—C7 | −101.0 (8) | C6'—C7'—C8'—C9' | −0.9 (12) |
C11—C6—C7—C8 | −0.2 (13) | C12'—O7'—C9'—C10' | −6.0 (11) |
O1—C6—C7—C8 | −178.9 (7) | C12'—O7'—C9'—C8' | 174.7 (7) |
C6—C7—C8—C9 | −0.7 (13) | C7'—C8'—C9'—C10' | 1.0 (12) |
C7—C8—C9—C10 | 0.5 (14) | C7'—C8'—C9'—O7' | −179.7 (7) |
C7—C8—C9—O7 | 179.1 (8) | O7'—C9'—C10'—C11' | −179.5 (7) |
C12—O7—C9—C10 | −4.2 (12) | C8'—C9'—C10'—C11' | −0.3 (12) |
C12—O7—C9—C8 | 177.2 (8) | C7'—C6'—C11'—C10' | 0.7 (12) |
C8—C9—C10—C11 | 0.6 (13) | O1'—C6'—C11'—C10' | −179.7 (7) |
O7—C9—C10—C11 | −177.9 (8) | C9'—C10'—C11'—C6' | −0.5 (12) |
C7—C6—C11—C10 | 1.3 (12) | C2'—O2'—C13'—O6' | 0.9 (11) |
O1—C6—C11—C10 | 179.9 (7) | C2'—O2'—C13'—C14' | −179.9 (6) |
C9—C10—C11—C6 | −1.5 (12) | O6'—C13'—C14'—C19' | −9.2 (12) |
C2—O2—C13—O6 | −1.0 (11) | O2'—C13'—C14'—C19' | 171.6 (7) |
C2—O2—C13—C14 | 179.5 (6) | O6'—C13'—C14'—C15' | 169.3 (8) |
O6—C13—C14—C19 | −6.8 (12) | O2'—C13'—C14'—C15' | −9.9 (11) |
O2—C13—C14—C19 | 172.7 (7) | C19'—C14'—C15'—C16' | 3.1 (13) |
O6—C13—C14—C15 | 170.1 (9) | C13'—C14'—C15'—C16' | −175.3 (8) |
O2—C13—C14—C15 | −10.4 (11) | C14'—C15'—C16'—C17' | −1.6 (13) |
C19—C14—C15—C16 | 3.1 (12) | C15'—C16'—C17'—C18' | −0.4 (13) |
C13—C14—C15—C16 | −173.8 (8) | C16'—C17'—C18'—C19' | 1.1 (13) |
C14—C15—C16—C17 | −2.3 (13) | C15'—C14'—C19'—C18' | −2.4 (13) |
C15—C16—C17—C18 | 0.1 (14) | C13'—C14'—C19'—C18' | 176.0 (8) |
C16—C17—C18—C19 | 1.3 (14) | C17'—C18'—C19'—C14' | 0.4 (13) |
C15—C14—C19—C18 | −1.7 (12) | C3'—O3'—C20'—C21' | 163.6 (6) |
C13—C14—C19—C18 | 175.3 (8) | O3'—C20'—C21'—C22' | 105.5 (9) |
C17—C18—C19—C14 | −0.5 (14) | O3'—C20'—C21'—C26' | −80.4 (9) |
C3—O3—C20—C21 | 169.6 (7) | C26'—C21'—C22'—C23' | 0.1 (12) |
O3—C20—C21—C22 | 86.6 (10) | C20'—C21'—C22'—C23' | 174.3 (8) |
O3—C20—C21—C26 | −97.4 (9) | C21'—C22'—C23'—C24' | −0.8 (13) |
C26—C21—C22—C23 | −1.5 (13) | C22'—C23'—C24'—C25' | 0.3 (13) |
C20—C21—C22—C23 | 174.5 (8) | C23'—C24'—C25'—C26' | 1.0 (13) |
C21—C22—C23—C24 | 0.6 (15) | C24'—C25'—C26'—C21' | −1.8 (13) |
C22—C23—C24—C25 | 0.2 (15) | C22'—C21'—C26'—C25' | 1.3 (12) |
C23—C24—C25—C26 | 0.1 (15) | C20'—C21'—C26'—C25' | −173.1 (8) |
C24—C25—C26—C21 | −1.0 (14) | C28'—O8'—C27'—C5' | −98.9 (7) |
C22—C21—C26—C25 | 1.7 (13) | O5'—C5'—C27'—O8' | 61.6 (8) |
C20—C21—C26—C25 | −174.4 (8) | C4'—C5'—C27'—O8' | −178.3 (6) |
C28—O8—C27—C5 | −99.2 (7) | C27'—O8'—C28'—O9' | −15.5 (11) |
O5—C5—C27—O8 | 62.4 (8) | C27'—O8'—C28'—C29' | 166.0 (6) |
C4—C5—C27—O8 | −176.2 (6) | O9'—C28'—C29'—Cl1' | −4.2 (11) |
C27—O8—C28—O9 | −15.3 (11) | O8'—C28'—C29'—Cl1' | 174.2 (5) |
C27—O8—C28—C29 | 166.2 (6) | C31'—O10'—C30'—O4' | 61.5 (8) |
O9—C28—C29—Cl1 | −1.6 (12) | C31'—O10'—C30'—C34' | −59.1 (8) |
O8—C28—C29—Cl1 | 176.8 (5) | C4'—O4'—C30'—O10' | 75.7 (7) |
C4—O4—C30—O10 | 75.9 (7) | C4'—O4'—C30'—C34' | −163.8 (6) |
C4—O4—C30—C34 | −162.0 (6) | C30'—O10'—C31'—C35' | 178.2 (6) |
C31—O10—C30—O4 | 60.0 (8) | C30'—O10'—C31'—C32' | 56.4 (8) |
C31—O10—C30—C34 | −60.6 (8) | C45'—O14'—C32'—C33' | 103.8 (8) |
C30—O10—C31—C35 | −177.8 (6) | C45'—O14'—C32'—C31' | −137.3 (7) |
C30—O10—C31—C32 | 60.0 (8) | O10'—C31'—C32'—O14' | −168.0 (6) |
C45—O14—C32—C33 | 108.6 (8) | C35'—C31'—C32'—O14' | 73.2 (9) |
C45—O14—C32—C31 | −134.0 (7) | O10'—C31'—C32'—C33' | −52.0 (9) |
O10—C31—C32—O14 | −172.3 (6) | C35'—C31'—C32'—C33' | −170.7 (7) |
C35—C31—C32—O14 | 69.4 (9) | C38A—O13'—C33'—C34' | −148.0 (15) |
O10—C31—C32—C33 | −56.4 (9) | C38B—O13'—C33'—C34' | −118.6 (15) |
C35—C31—C32—C33 | −174.8 (7) | C38A—O13'—C33'—C32' | 92.4 (15) |
C38—O13—C33—C34 | 62.7 (9) | C38B—O13'—C33'—C32' | 121.9 (14) |
C38—O13—C33—C32 | −64.6 (9) | O14'—C32'—C33'—O13' | −72.0 (8) |
O14—C32—C33—O13 | −58.5 (8) | C31'—C32'—C33'—O13' | 172.7 (7) |
C31—C32—C33—O13 | −173.3 (7) | O14'—C32'—C33'—C34' | 169.4 (6) |
O14—C32—C33—C34 | 172.0 (6) | C31'—C32'—C33'—C34' | 54.1 (9) |
C31—C32—C33—C34 | 57.2 (9) | N2'—N1'—C34'—C33' | −91.5 (9) |
N2—N1—C34—C33 | −72.2 (10) | N2'—N1'—C34'—C30' | 147.0 (8) |
N2—N1—C34—C30 | 168.3 (8) | O13'—C33'—C34'—N1' | 63.7 (9) |
O13—C33—C34—N1 | 56.6 (9) | C32'—C33'—C34'—N1' | −176.3 (6) |
C32—C33—C34—N1 | −174.5 (6) | O13'—C33'—C34'—C30' | −177.2 (7) |
O13—C33—C34—C30 | 174.9 (7) | C32'—C33'—C34'—C30' | −57.1 (9) |
C32—C33—C34—C30 | −56.1 (9) | O10'—C30'—C34'—N1' | −179.8 (7) |
O4—C30—C34—N1 | 55.2 (8) | O4'—C30'—C34'—N1' | 57.3 (9) |
O10—C30—C34—N1 | 178.8 (7) | O10'—C30'—C34'—C33' | 58.4 (9) |
O4—C30—C34—C33 | −66.8 (8) | O4'—C30'—C34'—C33' | −64.5 (9) |
O10—C30—C34—C33 | 56.8 (9) | C36'—O11'—C35'—C31' | 99.2 (9) |
C36—O11—C35—C31 | 97.7 (9) | O10'—C31'—C35'—O11' | 71.6 (8) |
O10—C31—C35—O11 | 75.3 (8) | C32'—C31'—C35'—O11' | −168.2 (7) |
C32—C31—C35—O11 | −165.5 (7) | C35'—O11'—C36'—O12' | −4.9 (14) |
C35—O11—C36—O12 | −4.6 (13) | C35'—O11'—C36'—C37' | 179.0 (7) |
C35—O11—C36—C37 | 178.4 (7) | C44'—C39'—C40'—C41' | −0.1 (14) |
C33—O13—C38—C39 | −171.9 (7) | C38A—C39'—C40'—C41' | −175.8 (11) |
O13—C38—C39—C40 | −24.3 (12) | C38B—C39'—C40'—C41' | 174.6 (13) |
O13—C38—C39—C44 | 157.6 (8) | C39'—C40'—C41'—C42' | −0.9 (16) |
C44—C39—C40—C41 | −0.7 (15) | C40'—C41'—C42'—C43' | 0.5 (18) |
C38—C39—C40—C41 | −178.8 (9) | C41'—C42'—C43'—C44' | 0.8 (19) |
C39—C40—C41—C42 | 1.6 (16) | C40'—C39'—C44'—C43' | 1.3 (15) |
C40—C41—C42—C43 | −0.5 (16) | C38A—C39'—C44'—C43' | 175.9 (13) |
C41—C42—C43—C44 | −1.4 (16) | C38B—C39'—C44'—C43' | −174.9 (11) |
C40—C39—C44—C43 | −1.2 (14) | C42'—C43'—C44'—C39' | −1.7 (17) |
C38—C39—C44—C43 | 176.9 (8) | C46'—O16'—C45'—O15' | 3.3 (13) |
C42—C43—C44—C39 | 2.3 (15) | C46'—O16'—C45'—O14' | −177.1 (6) |
C46—O16—C45—O15 | 0.4 (12) | C32'—O14'—C45'—O15' | 15.4 (13) |
C46—O16—C45—O14 | −177.1 (6) | C32'—O14'—C45'—O16' | −164.2 (6) |
C32—O14—C45—O15 | 14.6 (12) | C45'—O16'—C46'—C47' | 116.1 (8) |
C32—O14—C45—O16 | −167.9 (6) | O16'—C46'—C47'—C48' | −67.0 (9) |
C45—O16—C46—C47 | 128.0 (7) | O16'—C46'—C47'—C59' | 179.9 (6) |
O16—C46—C47—C48 | −68.4 (9) | C46'—C47'—C48'—C49' | 67.3 (11) |
O16—C46—C47—C59 | 177.2 (6) | C59'—C47'—C48'—C49' | −175.8 (8) |
C46—C47—C48—C49 | 63.1 (11) | C46'—C47'—C48'—C53' | −110.8 (8) |
C59—C47—C48—C49 | −177.8 (8) | C59'—C47'—C48'—C53' | 6.1 (9) |
C46—C47—C48—C53 | −116.2 (8) | C53'—C48'—C49'—C50' | 3.2 (12) |
C59—C47—C48—C53 | 2.9 (9) | C47'—C48'—C49'—C50' | −174.7 (8) |
C53—C48—C49—C50 | 2.9 (12) | C48'—C49'—C50'—C51' | −2.9 (13) |
C47—C48—C49—C50 | −176.4 (8) | C49'—C50'—C51'—C52' | 0.9 (14) |
C48—C49—C50—C51 | −1.3 (13) | C50'—C51'—C52'—C53' | 0.8 (13) |
C49—C50—C51—C52 | −0.7 (14) | C51'—C52'—C53'—C48' | −0.5 (12) |
C50—C51—C52—C53 | 1.1 (14) | C51'—C52'—C53'—C54' | 179.8 (8) |
C51—C52—C53—C48 | 0.4 (13) | C49'—C48'—C53'—C52' | −1.6 (12) |
C51—C52—C53—C54 | 179.4 (9) | C47'—C48'—C53'—C52' | 176.7 (7) |
C49—C48—C53—C52 | −2.5 (13) | C49'—C48'—C53'—C54' | 178.2 (7) |
C47—C48—C53—C52 | 176.9 (8) | C47'—C48'—C53'—C54' | −3.5 (9) |
C49—C48—C53—C54 | 178.3 (7) | C52'—C53'—C54'—C55' | 1.5 (15) |
C47—C48—C53—C54 | −2.3 (9) | C48'—C53'—C54'—C55' | −178.3 (9) |
C52—C53—C54—C59 | −178.5 (9) | C52'—C53'—C54'—C59' | 178.9 (9) |
C48—C53—C54—C59 | 0.6 (10) | C48'—C53'—C54'—C59' | −0.9 (9) |
C52—C53—C54—C55 | 1.9 (16) | C59'—C54'—C55'—C56' | −1.3 (12) |
C48—C53—C54—C55 | −179.1 (9) | C53'—C54'—C55'—C56' | 175.8 (8) |
C59—C54—C55—C56 | −1.2 (13) | C54'—C55'—C56'—C57' | 0.1 (13) |
C53—C54—C55—C56 | 178.4 (9) | C55'—C56'—C57'—C58' | 1.6 (13) |
C54—C55—C56—C57 | 1.1 (14) | C56'—C57'—C58'—C59' | −2.2 (13) |
C55—C56—C57—C58 | −1.1 (14) | C57'—C58'—C59'—C54' | 1.0 (12) |
C56—C57—C58—C59 | 1.1 (13) | C57'—C58'—C59'—C47' | 178.7 (8) |
C57—C58—C59—C54 | −1.2 (12) | C55'—C54'—C59'—C58' | 0.8 (12) |
C57—C58—C59—C47 | 179.1 (8) | C53'—C54'—C59'—C58' | −177.0 (7) |
C55—C54—C59—C58 | 1.3 (13) | C55'—C54'—C59'—C47' | −177.3 (7) |
C53—C54—C59—C58 | −178.4 (7) | C53'—C54'—C59'—C47' | 4.9 (9) |
C55—C54—C59—C47 | −179.0 (7) | C46'—C47'—C59'—C58' | −64.3 (11) |
C53—C54—C59—C47 | 1.3 (9) | C48'—C47'—C59'—C58' | 175.5 (8) |
C46—C47—C59—C58 | −61.0 (11) | C46'—C47'—C59'—C54' | 113.6 (8) |
C48—C47—C59—C58 | 177.1 (8) | C48'—C47'—C59'—C54' | −6.6 (8) |
C46—C47—C59—C54 | 119.3 (8) | C33'—O13'—C38A—C39' | 149.3 (12) |
C48—C47—C59—C54 | −2.6 (8) | C44'—C39'—C38A—O13' | −57 (2) |
C6'—O1'—C1'—O5' | −91.4 (7) | C40'—C39'—C38A—O13' | 118.4 (16) |
C6'—O1'—C1'—C2' | 150.3 (6) | C33'—O13'—C38B—C39' | 175.2 (13) |
C5'—O5'—C1'—O1' | −173.9 (6) | C44'—C39'—C38B—O13' | −100.1 (17) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O6′ | 1.00 | 2.32 | 3.265 (10) | 157 |
C1′—H1′···O6i | 1.00 | 2.33 | 3.276 (10) | 157 |
C4—H4···O8′ii | 1.00 | 2.56 | 3.512 (9) | 159 |
C4′—H4′···O8 | 1.00 | 2.55 | 3.508 (9) | 160 |
C27—H27A···O10′ | 0.99 | 2.63 | 3.507 (10) | 148 |
C29—H29A···O9′ | 0.99 | 2.33 | 3.258 (11) | 156 |
C29′—H29C···O9i | 0.99 | 2.35 | 3.273 (8) | 154 |
C34′—H34′···O13 | 1.00 | 2.54 | 3.529 (7) | 172 |
C35—H35B···O14′ii | 0.99 | 2.49 | 3.476 (7) | 174 |
C35′—H35D···O14 | 0.99 | 2.63 | 3.569 (10) | 158 |
C44—H44···Cg1ii | 0.95 | 2.91 | 3.849 (10) | 171 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C59H56ClN3O16 |
Mr | 1098.52 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 123 |
a, b, c (Å) | 10.454 (2), 35.610 (7), 14.408 (3) |
β (°) | 95.61 (3) |
V (Å3) | 5338.0 (19) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 1.27 |
Crystal size (mm) | 0.80 × 0.08 × 0.04 |
Data collection | |
Diffractometer | Rigaku Spider diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.68, 1.0 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 35705, 12625, 8360 |
Rint | 0.055 |
θmax (°) | 55.0 |
(sin θ/λ)max (Å−1) | 0.531 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.057, 0.155, 1.00 |
No. of reflections | 12625 |
No. of parameters | 1426 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.32, −0.30 |
Absolute structure | Flack x determined using 2859 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons & Flack, 2004) |
Absolute structure parameter | 0.035 (11) |
Computer programs: CrystalClear (Rigaku, 2005), FSProcess (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), ORTEP-3 in WinGX (Farrugia, 2012), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2008).
Cl1—C29 | 1.774 (8) | Cl1'—C29' | 1.781 (7) |
O4—C4 | 1.435 (8) | O4'—C4' | 1.439 (8) |
N1—N2 | 1.248 (10) | N1'—N2' | 1.214 (12) |
N1—C34 | 1.468 (10) | N1'—C34' | 1.476 (10) |
N2—N3 | 1.146 (10) | N2'—N3' | 1.218 (12) |
N2—N1—C34 | 113.7 (7) | N2'—N1'—C34' | 107.8 (8) |
N3—N2—N1 | 171.6 (10) | N3'—N2'—N1' | 171.3 (12) |
C30—O4—C4—C3 | 88.9 (7) | C30'—O4'—C4'—C3' | 94.1 (7) |
C31—O10—C30—O4 | 60.0 (8) | C31'—O10'—C30'—O4' | 61.5 (8) |
C38—O13—C33—C34 | 62.7 (9) | C38B—O13'—C33'—C34' | −118.6 (15) |
C33—O13—C38—C39 | −171.9 (7) | C33'—O13'—C38A—C39' | 149.3 (12) |
O13—C38—C39—C40 | −24.3 (12) | C33'—O13'—C38B—C39' | 175.2 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···O6' | 1.00 | 2.32 | 3.265 (10) | 157 |
C1'—H1'···O6i | 1.00 | 2.33 | 3.276 (10) | 157 |
C4—H4···O8'ii | 1.00 | 2.56 | 3.512 (9) | 159 |
C4'—H4'···O8 | 1.00 | 2.55 | 3.508 (9) | 160 |
C27—H27A···O10' | 0.99 | 2.63 | 3.507 (10) | 147.9 |
C29—H29A···O9' | 0.99 | 2.33 | 3.258 (11) | 156 |
C29'—H29C···O9i | 0.99 | 2.35 | 3.273 (8) | 154 |
C34'—H34'···O13 | 1.00 | 2.54 | 3.529 (7) | 172 |
C35—H35B···O14'ii | 0.99 | 2.49 | 3.476 (7) | 174 |
C35'—H35D···O14 | 0.99 | 2.63 | 3.569 (10) | 158.1 |
C44—H44···Cg1ii | 0.95 | 2.91 | 3.849 (10) | 171 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y, z. |
Compound | Q (Å) | θ (%) | ϕ (%) | Head_Db | Foot_Db |
C1–C5/O5 | 0.588 (8) | 11.8 (8) | 293 (4) | 0.748 (8) | -0.586 (8) |
C1'–C5'/O5' | 0.594 (8) | 14.6 (8) | 288 (3) | 0.768 (8) | -0.566 (8) |
C30–C34/O10 | 0.582 (8) | 0.0 (8) | 202 (41) | 0.666 (8) | -0.692 (8) |
C31'–C34'/O10' | 0.561 (9) | 3.9 (9) | 116 (13) | 0.675 (8) | -0.648 (8) |
RAVNAD-1 | 0.597 (3) | 7.5 (3) | 89 (2) | 0.727 (4) | -0.652 (4) |
RAVNAD-2 | 0.577 (3) | 13.8 (3) | 340.8 (13) | 0.713 (4) | -0.555 (5) |
Reference: (a) Cremer & Pople (1975); Note: (b) the distance (Å) from the four-atom `seat' plane |
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Heparan sulfate (HS) is a linear polysaccharide with a disaccharide repeating unit of D-glucosamine and L-iduronic or D-glucuronic acid, which can be O- or N-sulfated or N-acetylated. HS is involved in the regulation of many important biological processes (Bishop et al., 2007; Turnbull et al., 2001), involving growth factors (Mohammadi et al., 2005), cytokines (Lortat-Jacob, 2009) and stem cells (Piecewicz & Sengupta, 2011). In addition, HS was identified as a regulator of the cleavage of the amyloid precursor protein by β-secretase (BACE1), which is a critical step in the formation of the amyloid plaques that are found in the brains of people suffering from Alzheimer's disease (Scholefield et al., 2003). Homogenous HS polymers derived from chemically modified heparin fragments have demonstrated potent inhibition of BACE1 without any significant anticoagulant activity (Scholefield et al., 2003; Patey et al., 2008). Therefore synthetic HS–oligosaccharides with high potency as BACE1 inhibitors might have an application as novel therapeutics for Alzheimer's disease.
In a recent paper (Schwörer et al., 2013), we describe the synthesis and inhibition data of a library of such oligosaccharides. At the centre of the synthetic methodology are two highly orthogonally protected disaccharide building blocks, one of them being the title compound, (I). This disaccharide can serve as a glycosyl acceptor by removal of the Fmoc group (see Scheme) or can be converted into a glycosyl donor by hydrolysis of the methoxyphenyl glycoside and formation of the corresponding trichloroacemidate; the azide and the orthogonal ester protecting groups provide selective access to further functionalization later in the synthesis.
The crystal contains two enantiomerically identical molecules which are related by translation along the a axis and separated by almost exactly half a cell (Fig. 1). Atom labels of the two molecules are related by the addition of a prime for the second molecule (Fig. 1). Just one benzyl group is oriented differently (atoms C38–C44/C38A and C39'–C44'), breaking this novel translational relationship: confirmation is given by the dihedral angles (e.g. C38—O13—C33—C34) shown in Table 1. The second molecule (primed labels) is disordered at the C38' site into two sites (C38A/C38B); only the major site atom (C38A) is shown in Fig. 1. An overlap view of the molecules confirms their close similarity (Fig. 2). The geometric parameters are essentially the same (Table 1) with the corresponding pyranose rings in closely related chair con formations (Table 2). The observed absolute configurations confirmed the expected stereochemistry: C1,1'(S), C2,2'(R), C3,3'(S), C4,4'(S), C5,5'(R), C30,30'(S), C31,31'(R), C32,32'(S), C33,33'(R), C34,34'(R).
There are few reported crystal structures of disaccharide molecules [Cambridge Structiral Database (CSD); Allen, 2002]: one glucopyranose (CSD refcode RAVNAD; Abboud et al., 1997) and one idopyranose (AQOGIW; Lee et al., 2004) relative. The conformational data given in Table 2 (Cremer & Pople, 1975) show that the essential pyranose chair conformations have not been disturbed significantly in the title compound.
The packing in the crystal of (I) is dominated by strong C—H···O interactions which efficiently bind the molecules related along both the a (Fig. 3) and c axes (Table 3). These interactions form a three-dimensional network in which R22 and C22 motifs (Bernstein et al., 1995) involving 8, 11, 13, 15, 18, 22 and 25 atoms are found, e.g. R22(11) is clearly seen in Fig. 3.
The question that arises from this analysis concerns why there are two nearly identical molecules almost exactly one-half cell apart, while a single molecule per asymetric unit in a cell with half the axial length would seem to be a logical and similar arrangement. Indeed, contacts between the molecules principally involve C—H···O interactions (Table 3). There seems to be only one notable exception: a C–H···π interaction (last entry, Table 3 where Cg1 is the centroid of the C39'–C44' ring) involving both phenyl groups (H44 on C44 to the centroid of the `alternatively oriented' C39'–C44' phenyl ring). This is probably fortuitous, but we note that all the other C—H···π interactions have less favourable X—H···centroid angles (114–141°) compared with the value of 171° observed for (I).