Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270113006288/ku3090sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113006288/ku3090I_296Ksup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270113006288/ku3090I_120Ksup3.hkl | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113006288/ku3090I_296Ksup4.cml | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S0108270113006288/ku3090I_120Ksup5.cml |
CCDC references: 934625; 934626
For both compounds, data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
C48H52N2O6 | F(000) = 1608 |
Mr = 752.92 | Dx = 1.202 Mg m−3 Dm = 1.19 Mg m−3 Dm measured by flotation in aqueous KI |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 23192 reflections |
a = 12.0729 (10) Å | θ = 2.2–27.1° |
b = 29.176 (2) Å | µ = 0.08 mm−1 |
c = 11.8511 (9) Å | T = 296 K |
β = 94.417 (1)° | Diamond, yellow |
V = 4162.0 (6) Å3 | 0.60 × 0.40 × 0.20 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 9074 independent reflections |
Radiation source: fine-focus sealed tube | 6318 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 27.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −15→15 |
Tmin = 0.954, Tmax = 0.984 | k = −37→37 |
57486 measured reflections | l = −15→15 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.167 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.12 | w = 1/[σ2(Fo2) + (0.0784P)2 + 0.8499P] where P = (Fo2 + 2Fc2)/3 |
9074 reflections | (Δ/σ)max = 0.011 |
718 parameters | Δρmax = 0.27 e Å−3 |
330 restraints | Δρmin = −0.19 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 | Occ. (<1) | |
O1 | 0.03159 (10) | 0.10405 (4) | 0.40845 (11) | 0.0513 (3) | |
H101 | 0.0378 (18) | 0.1322 (9) | 0.4119 (19) | 0.076 (7)* | |
C1 | 0.11831 (13) | 0.08237 (5) | 0.46690 (13) | 0.0375 (3) | |
C2 | 0.19168 (13) | 0.10756 (5) | 0.53754 (13) | 0.0404 (3) | |
N1 | −0.09197 (13) | 0.00457 (5) | 0.22064 (13) | 0.0541 (4) | |
H111 | −0.0755 (17) | −0.0275 (8) | 0.2202 (18) | 0.074 (6)* | |
O3 | 0.01569 (12) | −0.06592 (4) | 0.29139 (11) | 0.0592 (3) | |
C3 | 0.27773 (14) | 0.08460 (5) | 0.60106 (15) | 0.0470 (4) | |
C4 | 0.28665 (14) | 0.03782 (5) | 0.58942 (15) | 0.0471 (4) | |
H4 | 0.3505 (16) | 0.0225 (6) | 0.6372 (16) | 0.055 (5)* | |
O5 | 0.05666 (12) | 0.15119 (4) | 0.68791 (11) | 0.0566 (3) | |
H105 | 0.0675 (18) | 0.1225 (8) | 0.6757 (18) | 0.071 (6)* | |
C5 | 0.23054 (14) | −0.03771 (5) | 0.50491 (14) | 0.0456 (4) | |
N2 | −0.07555 (13) | 0.24166 (5) | 0.87614 (13) | 0.0529 (4) | |
H112 | −0.070 (2) | 0.2743 (9) | 0.879 (2) | 0.098 (8)* | |
C6 | 0.16297 (15) | −0.06073 (5) | 0.42823 (15) | 0.0476 (4) | |
O4 | 0.17625 (14) | −0.10644 (4) | 0.40741 (14) | 0.0687 (4) | |
H104 | 0.116 (3) | −0.1102 (11) | 0.351 (3) | 0.123 (11)* | |
C7 | 0.07358 (14) | −0.03964 (5) | 0.36041 (14) | 0.0435 (4) | |
O7 | −0.00972 (13) | 0.31778 (4) | 0.80541 (13) | 0.0745 (4) | |
C8 | 0.05471 (13) | 0.00819 (5) | 0.37036 (13) | 0.0382 (3) | |
O8 | 0.09906 (15) | 0.36915 (4) | 0.67585 (14) | 0.0763 (5) | |
H108 | 0.052 (3) | 0.3703 (11) | 0.738 (3) | 0.129 (11)* | |
C9 | 0.12742 (12) | 0.03436 (4) | 0.45076 (12) | 0.0357 (3) | |
C10 | 0.21447 (13) | 0.01167 (5) | 0.51592 (13) | 0.0398 (3) | |
C11 | 0.11545 (13) | 0.17841 (5) | 0.62055 (13) | 0.0405 (3) | |
C12 | 0.18081 (13) | 0.15884 (5) | 0.54295 (14) | 0.0418 (4) | |
C13 | 0.23957 (15) | 0.18736 (5) | 0.47280 (15) | 0.0505 (4) | |
C14 | 0.22926 (16) | 0.23426 (6) | 0.48383 (16) | 0.0519 (4) | |
H14 | 0.2699 (16) | 0.2535 (7) | 0.4336 (17) | 0.061 (5)* | |
C15 | 0.15948 (16) | 0.30496 (5) | 0.57225 (15) | 0.0500 (4) | |
C16 | 0.10309 (16) | 0.32290 (5) | 0.65579 (16) | 0.0533 (4) | |
C17 | 0.04275 (16) | 0.29584 (5) | 0.73236 (16) | 0.0516 (4) | |
C18 | 0.04221 (13) | 0.24731 (5) | 0.72224 (13) | 0.0414 (3) | |
C19 | 0.10593 (13) | 0.22662 (5) | 0.63609 (13) | 0.0390 (3) | |
C20 | 0.16500 (14) | 0.25494 (5) | 0.56330 (14) | 0.0444 (4) | |
C21 | 0.35858 (18) | 0.11124 (7) | 0.6794 (2) | 0.0666 (5) | |
H21A | 0.416 (2) | 0.0901 (8) | 0.724 (2) | 0.080* | 0.72 (2) |
H21B | 0.317 (2) | 0.1305 (10) | 0.737 (2) | 0.080* | 0.72 (2) |
H21C | 0.401 (2) | 0.1335 (9) | 0.629 (2) | 0.080* | 0.72 (2) |
H21D | 0.350 (6) | 0.1466 (6) | 0.686 (6) | 0.080* | 0.28 (2) |
H21E | 0.341 (6) | 0.096 (2) | 0.756 (3) | 0.080* | 0.28 (2) |
H21F | 0.441 (2) | 0.104 (2) | 0.665 (6) | 0.080* | 0.28 (2) |
C22 | −0.03030 (14) | 0.02755 (5) | 0.29787 (14) | 0.0448 (4) | |
H22 | −0.0461 (15) | 0.0625 (6) | 0.3018 (15) | 0.052 (5)* | |
C23 | 0.32468 (18) | −0.06217 (6) | 0.5722 (2) | 0.0656 (5) | |
H23 | 0.3463 (18) | −0.0433 (8) | 0.6340 (19) | 0.071 (6)* | |
C24 | 0.2927 (3) | −0.10797 (8) | 0.6252 (2) | 0.0963 (9) | |
H24A | 0.2850 | −0.1311 | 0.5676 | 0.144* | |
H24B | 0.2235 | −0.1045 | 0.6592 | 0.144* | |
H24C | 0.3496 | −0.1169 | 0.6821 | 0.144* | |
C25 | 0.4224 (2) | −0.06788 (11) | 0.5005 (3) | 0.1105 (10) | |
H25A | 0.4014 | −0.0873 | 0.4371 | 0.166* | |
H25B | 0.4834 | −0.0815 | 0.5453 | 0.166* | |
H25C | 0.4444 | −0.0384 | 0.4739 | 0.166* | |
C26 | 0.3125 (2) | 0.16735 (7) | 0.3879 (2) | 0.0715 (6) | |
H26A | 0.316 (4) | 0.1903 (11) | 0.321 (3) | 0.086* | 0.62 (6) |
H26B | 0.3917 (18) | 0.164 (2) | 0.428 (3) | 0.086* | 0.62 (6) |
H26C | 0.286 (4) | 0.1355 (9) | 0.357 (4) | 0.086* | 0.62 (6) |
H26D | 0.364 (6) | 0.143 (2) | 0.429 (4) | 0.086* | 0.38 (6) |
H26F | 0.261 (4) | 0.151 (3) | 0.325 (5) | 0.086* | 0.38 (6) |
H26E | 0.362 (6) | 0.1913 (16) | 0.350 (6) | 0.086* | 0.38 (6) |
C27 | −0.02006 (14) | 0.22277 (5) | 0.79844 (14) | 0.0441 (4) | |
H27 | −0.0225 (15) | 0.1887 (7) | 0.7928 (15) | 0.058 (5)* | |
C28 | 0.2208 (2) | 0.33572 (6) | 0.49415 (19) | 0.0682 (6) | |
H28 | 0.2269 (17) | 0.3189 (8) | 0.4210 (19) | 0.075 (6)* | |
C29 | 0.1581 (3) | 0.37939 (7) | 0.4536 (2) | 0.0906 (8) | |
H29A | 0.1608 | 0.4014 | 0.5140 | 0.136* | |
H29B | 0.0821 | 0.3719 | 0.4315 | 0.136* | |
H29C | 0.1922 | 0.3921 | 0.3901 | 0.136* | |
C30 | 0.3345 (2) | 0.34742 (10) | 0.5490 (3) | 0.1007 (9) | |
H30A | 0.3267 | 0.3650 | 0.6164 | 0.151* | |
H30B | 0.3747 | 0.3650 | 0.4972 | 0.151* | |
H30C | 0.3744 | 0.3197 | 0.5681 | 0.151* | |
C31 | −0.17321 (19) | 0.02641 (8) | 0.14102 (19) | 0.0661 (5) | |
H31A | −0.2287 (19) | 0.0025 (8) | 0.1132 (19) | 0.081 (7)* | |
H31B | −0.215 (2) | 0.0514 (10) | 0.181 (2) | 0.106 (9)* | |
C32 | −0.1201 (3) | 0.04872 (14) | 0.0435 (3) | 0.1055 (12) | |
H32A | −0.060 (3) | 0.0683 (13) | 0.067 (3) | 0.142 (13)* | |
H32B | −0.084 (3) | 0.0223 (15) | 0.004 (4) | 0.175 (19)* | |
C33 | −0.2021 (3) | 0.07249 (13) | −0.0413 (3) | 0.1188 (13) | |
H33A | −0.166 (4) | 0.0916 (17) | −0.092 (4) | 0.205 (19)* | |
H33B | −0.253 (2) | 0.0925 (11) | 0.012 (3) | 0.109 (11)* | |
C34B | −0.2962 (8) | 0.0443 (3) | −0.0919 (6) | 0.104 (3) | 0.439 (18) |
C35B | −0.2808 (15) | 0.0093 (4) | −0.1663 (8) | 0.139 (4) | 0.439 (18) |
H35B | −0.2091 | 0.0031 | −0.1856 | 0.167* | 0.439 (18) |
C36B | −0.3663 (17) | −0.0170 (5) | −0.2135 (11) | 0.158 (4) | 0.439 (18) |
H36B | −0.3547 | −0.0407 | −0.2639 | 0.189* | 0.439 (18) |
C37B | −0.4698 (15) | −0.0063 (6) | −0.1819 (12) | 0.150 (5) | 0.439 (18) |
H37B | −0.5305 | −0.0231 | −0.2118 | 0.180* | 0.439 (18) |
C38B | −0.4866 (10) | 0.0286 (6) | −0.1078 (14) | 0.135 (4) | 0.439 (18) |
H38B | −0.5584 | 0.0347 | −0.0885 | 0.162* | 0.439 (18) |
C39B | −0.4006 (7) | 0.0545 (5) | −0.0614 (12) | 0.118 (3) | 0.439 (18) |
H39B | −0.4123 | 0.0781 | −0.0110 | 0.142* | 0.439 (18) |
C40 | −0.13950 (19) | 0.21677 (7) | 0.95544 (17) | 0.0570 (5) | |
H40A | −0.0896 (18) | 0.1973 (8) | 1.0048 (19) | 0.073 (6)* | |
H40B | −0.1861 (18) | 0.1946 (8) | 0.9150 (19) | 0.075 (6)* | |
C41 | −0.20324 (17) | 0.24965 (7) | 1.02361 (17) | 0.0537 (4) | |
H41A | −0.1479 (19) | 0.2709 (8) | 1.0595 (19) | 0.073 (6)* | |
H41B | −0.2485 (19) | 0.2683 (8) | 0.9692 (19) | 0.075 (7)* | |
C42 | −0.2668 (2) | 0.22580 (7) | 1.1111 (2) | 0.0639 (5) | |
H42A | −0.213 (2) | 0.2071 (9) | 1.158 (2) | 0.091 (8)* | |
H42B | −0.314 (2) | 0.2035 (9) | 1.074 (2) | 0.087 (8)* | |
C43 | −0.33201 (16) | 0.25663 (7) | 1.18402 (16) | 0.0569 (4) | |
C44 | −0.3204 (2) | 0.30389 (8) | 1.18609 (19) | 0.0684 (5) | |
H44 | −0.268 (2) | 0.3186 (8) | 1.136 (2) | 0.087 (7)* | |
C45 | −0.3780 (2) | 0.33118 (9) | 1.2575 (2) | 0.0804 (7) | |
H45 | −0.366 (2) | 0.3671 (11) | 1.258 (2) | 0.113 (9)* | |
C46 | −0.4480 (2) | 0.31201 (11) | 1.3279 (2) | 0.0927 (8) | |
H46 | −0.489 (3) | 0.3316 (11) | 1.383 (3) | 0.127 (10)* | |
C47 | −0.4606 (2) | 0.26522 (13) | 1.3287 (3) | 0.1036 (10) | |
H47 | −0.508 (3) | 0.2511 (11) | 1.391 (3) | 0.131 (10)* | |
C48 | −0.4033 (2) | 0.23778 (10) | 1.2574 (2) | 0.0845 (7) | |
H48 | −0.413 (2) | 0.2053 (11) | 1.257 (3) | 0.115 (10)* | |
C34A | −0.2828 (5) | 0.03929 (17) | −0.0997 (3) | 0.0766 (18) | 0.561 (18) |
C35A | −0.2417 (8) | 0.0032 (2) | −0.1580 (5) | 0.095 (2) | 0.561 (18) |
H35A | −0.1651 | 0.0003 | −0.1597 | 0.114* | 0.561 (18) |
C36A | −0.3082 (9) | −0.0287 (3) | −0.2136 (5) | 0.110 (3) | 0.561 (18) |
H36A | −0.2777 | −0.0528 | −0.2523 | 0.132* | 0.561 (18) |
C37A | −0.4208 (8) | −0.0245 (3) | −0.2111 (6) | 0.113 (3) | 0.561 (18) |
H37A | −0.4674 | −0.0459 | −0.2485 | 0.135* | 0.561 (18) |
C38A | −0.4658 (7) | 0.0110 (3) | −0.1541 (9) | 0.122 (3) | 0.561 (18) |
H38A | −0.5425 | 0.0137 | −0.1527 | 0.146* | 0.561 (18) |
C39A | −0.3962 (5) | 0.0424 (3) | −0.0992 (8) | 0.101 (2) | 0.561 (18) |
H39A | −0.4268 | 0.0664 | −0.0605 | 0.122* | 0.561 (18) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0616 (8) | 0.0240 (5) | 0.0666 (8) | 0.0021 (5) | −0.0071 (6) | 0.0001 (5) |
C1 | 0.0437 (8) | 0.0268 (6) | 0.0426 (8) | 0.0005 (6) | 0.0079 (6) | −0.0005 (6) |
C2 | 0.0445 (9) | 0.0282 (7) | 0.0493 (9) | −0.0016 (6) | 0.0096 (7) | −0.0079 (6) |
N1 | 0.0624 (9) | 0.0428 (8) | 0.0554 (9) | −0.0078 (7) | −0.0066 (7) | −0.0010 (7) |
O3 | 0.0818 (9) | 0.0307 (5) | 0.0634 (8) | −0.0115 (5) | −0.0044 (7) | −0.0079 (5) |
C3 | 0.0454 (9) | 0.0391 (8) | 0.0565 (10) | −0.0020 (7) | 0.0033 (7) | −0.0114 (7) |
C4 | 0.0446 (9) | 0.0393 (8) | 0.0566 (10) | 0.0039 (7) | −0.0003 (8) | −0.0071 (7) |
O5 | 0.0833 (9) | 0.0256 (5) | 0.0645 (8) | −0.0071 (5) | 0.0281 (7) | −0.0064 (5) |
C5 | 0.0513 (10) | 0.0314 (7) | 0.0546 (9) | 0.0066 (6) | 0.0063 (7) | −0.0030 (7) |
N2 | 0.0654 (10) | 0.0404 (7) | 0.0550 (9) | −0.0090 (6) | 0.0185 (7) | −0.0115 (6) |
C6 | 0.0601 (10) | 0.0245 (7) | 0.0590 (10) | 0.0026 (6) | 0.0102 (8) | −0.0054 (6) |
O4 | 0.0875 (10) | 0.0273 (6) | 0.0897 (10) | 0.0093 (6) | −0.0035 (8) | −0.0133 (6) |
C7 | 0.0548 (10) | 0.0288 (7) | 0.0475 (9) | −0.0062 (6) | 0.0072 (7) | −0.0044 (6) |
O7 | 0.0999 (11) | 0.0358 (6) | 0.0942 (10) | −0.0123 (6) | 0.0494 (9) | −0.0231 (6) |
C8 | 0.0457 (8) | 0.0274 (7) | 0.0422 (8) | −0.0051 (6) | 0.0075 (6) | −0.0010 (6) |
O8 | 0.1195 (13) | 0.0262 (6) | 0.0887 (10) | −0.0061 (6) | 0.0438 (10) | −0.0102 (6) |
C9 | 0.0409 (8) | 0.0262 (6) | 0.0408 (7) | −0.0019 (5) | 0.0094 (6) | −0.0027 (5) |
C10 | 0.0439 (8) | 0.0296 (7) | 0.0465 (8) | 0.0015 (6) | 0.0087 (7) | −0.0034 (6) |
C11 | 0.0484 (9) | 0.0291 (7) | 0.0443 (8) | −0.0061 (6) | 0.0050 (7) | −0.0045 (6) |
C12 | 0.0472 (9) | 0.0281 (7) | 0.0506 (9) | −0.0033 (6) | 0.0069 (7) | −0.0089 (6) |
C13 | 0.0572 (10) | 0.0356 (8) | 0.0609 (10) | −0.0067 (7) | 0.0183 (8) | −0.0104 (7) |
C14 | 0.0640 (11) | 0.0344 (8) | 0.0598 (10) | −0.0107 (7) | 0.0215 (9) | −0.0085 (7) |
C15 | 0.0661 (11) | 0.0299 (7) | 0.0556 (10) | −0.0070 (7) | 0.0139 (8) | −0.0053 (7) |
C16 | 0.0718 (12) | 0.0253 (7) | 0.0645 (11) | −0.0063 (7) | 0.0169 (9) | −0.0075 (7) |
C17 | 0.0627 (11) | 0.0324 (8) | 0.0617 (10) | −0.0049 (7) | 0.0170 (8) | −0.0134 (7) |
C18 | 0.0486 (9) | 0.0301 (7) | 0.0460 (8) | −0.0053 (6) | 0.0064 (7) | −0.0083 (6) |
C19 | 0.0447 (9) | 0.0286 (7) | 0.0434 (8) | −0.0043 (6) | 0.0028 (7) | −0.0073 (6) |
C20 | 0.0543 (10) | 0.0296 (7) | 0.0497 (9) | −0.0056 (6) | 0.0077 (7) | −0.0066 (6) |
C21 | 0.0629 (12) | 0.0518 (10) | 0.0822 (14) | −0.0033 (9) | −0.0133 (11) | −0.0197 (10) |
C22 | 0.0513 (10) | 0.0356 (8) | 0.0474 (9) | −0.0057 (7) | 0.0026 (7) | −0.0010 (7) |
C23 | 0.0729 (14) | 0.0414 (9) | 0.0795 (14) | 0.0179 (9) | −0.0123 (11) | −0.0100 (9) |
C24 | 0.129 (2) | 0.0556 (13) | 0.0999 (19) | 0.0238 (14) | −0.0184 (17) | 0.0133 (12) |
C25 | 0.0682 (16) | 0.110 (2) | 0.153 (3) | 0.0323 (15) | 0.0098 (17) | 0.002 (2) |
C26 | 0.0888 (15) | 0.0438 (10) | 0.0878 (15) | −0.0087 (10) | 0.0436 (12) | −0.0166 (10) |
C27 | 0.0520 (10) | 0.0341 (7) | 0.0465 (9) | −0.0023 (6) | 0.0060 (7) | −0.0066 (6) |
C28 | 0.1062 (17) | 0.0357 (9) | 0.0674 (12) | −0.0104 (9) | 0.0368 (12) | −0.0041 (8) |
C29 | 0.147 (2) | 0.0482 (11) | 0.0796 (15) | −0.0022 (13) | 0.0278 (16) | 0.0102 (11) |
C30 | 0.0922 (19) | 0.0839 (17) | 0.132 (2) | −0.0218 (14) | 0.0495 (18) | 0.0127 (16) |
C31 | 0.0638 (13) | 0.0663 (12) | 0.0653 (12) | −0.0040 (10) | −0.0134 (10) | −0.0003 (10) |
C32 | 0.089 (2) | 0.117 (3) | 0.105 (2) | −0.034 (2) | −0.0261 (18) | 0.052 (2) |
C33 | 0.126 (3) | 0.108 (2) | 0.116 (3) | −0.021 (2) | −0.030 (2) | 0.052 (2) |
C34B | 0.092 (5) | 0.122 (6) | 0.095 (6) | −0.005 (5) | −0.017 (5) | 0.051 (5) |
C35B | 0.115 (7) | 0.188 (9) | 0.115 (7) | −0.005 (6) | 0.010 (5) | 0.012 (5) |
C36B | 0.150 (9) | 0.212 (10) | 0.107 (7) | 0.001 (8) | −0.020 (7) | −0.012 (7) |
C37B | 0.122 (7) | 0.194 (10) | 0.123 (8) | −0.006 (8) | −0.057 (6) | 0.005 (7) |
C38B | 0.099 (5) | 0.172 (9) | 0.130 (8) | 0.002 (5) | −0.020 (5) | 0.034 (6) |
C39B | 0.107 (5) | 0.137 (7) | 0.108 (6) | 0.013 (5) | −0.012 (4) | 0.030 (5) |
C40 | 0.0705 (13) | 0.0482 (10) | 0.0544 (11) | −0.0075 (9) | 0.0192 (10) | −0.0050 (8) |
C41 | 0.0568 (11) | 0.0547 (10) | 0.0508 (10) | −0.0027 (9) | 0.0115 (9) | −0.0019 (8) |
C42 | 0.0758 (14) | 0.0542 (11) | 0.0639 (12) | −0.0055 (10) | 0.0203 (11) | −0.0007 (10) |
C43 | 0.0544 (11) | 0.0627 (11) | 0.0547 (10) | −0.0001 (8) | 0.0102 (8) | 0.0048 (8) |
C44 | 0.0768 (14) | 0.0631 (12) | 0.0676 (13) | 0.0054 (10) | 0.0214 (11) | 0.0009 (10) |
C45 | 0.0916 (17) | 0.0764 (15) | 0.0743 (14) | 0.0244 (13) | 0.0135 (13) | −0.0004 (12) |
C46 | 0.0867 (18) | 0.108 (2) | 0.0869 (17) | 0.0333 (16) | 0.0302 (14) | 0.0023 (16) |
C47 | 0.0867 (19) | 0.126 (3) | 0.105 (2) | 0.0018 (17) | 0.0516 (17) | 0.0051 (19) |
C48 | 0.0839 (17) | 0.0793 (16) | 0.0946 (18) | −0.0086 (13) | 0.0348 (14) | 0.0069 (14) |
C34A | 0.080 (3) | 0.087 (4) | 0.060 (4) | −0.007 (3) | −0.013 (3) | 0.029 (3) |
C35A | 0.086 (4) | 0.140 (5) | 0.061 (3) | −0.007 (3) | 0.018 (2) | 0.010 (3) |
C36A | 0.127 (5) | 0.142 (5) | 0.060 (3) | −0.002 (4) | 0.003 (3) | −0.005 (3) |
C37A | 0.105 (5) | 0.143 (6) | 0.085 (4) | −0.021 (4) | −0.026 (4) | 0.012 (3) |
C38A | 0.086 (4) | 0.154 (6) | 0.119 (6) | 0.003 (4) | −0.037 (4) | 0.007 (5) |
C39A | 0.087 (4) | 0.111 (4) | 0.102 (4) | 0.019 (3) | −0.021 (3) | 0.007 (4) |
O1—C1 | 1.3654 (19) | C26—H26D | 1.044 (12) |
O1—H101 | 0.82 (2) | C26—H26F | 1.043 (12) |
C1—C2 | 1.383 (2) | C26—H26E | 1.040 (12) |
C1—C9 | 1.4190 (18) | C27—H27 | 0.996 (19) |
C2—C3 | 1.405 (2) | C28—C30 | 1.512 (4) |
C2—C12 | 1.5038 (19) | C28—C29 | 1.540 (3) |
N1—C22 | 1.318 (2) | C28—H28 | 1.00 (2) |
N1—C31 | 1.455 (3) | C29—H29A | 0.9600 |
N1—H111 | 0.96 (2) | C29—H29B | 0.9600 |
O3—C7 | 1.2873 (19) | C29—H29C | 0.9600 |
C3—C4 | 1.377 (2) | C30—H30A | 0.9600 |
C3—C21 | 1.510 (2) | C30—H30B | 0.9600 |
C4—C10 | 1.408 (2) | C30—H30C | 0.9600 |
C4—H4 | 1.023 (19) | C31—C32 | 1.511 (4) |
O5—C11 | 1.3635 (18) | C31—H31A | 1.01 (2) |
O5—H105 | 0.86 (2) | C31—H31B | 1.02 (3) |
C5—C6 | 1.352 (2) | C32—C33 | 1.523 (4) |
C5—C10 | 1.461 (2) | C32—H32A | 0.95 (4) |
C5—C23 | 1.516 (3) | C32—H32B | 1.02 (4) |
N2—C27 | 1.302 (2) | C33—C34B | 1.491 (8) |
N2—C40 | 1.456 (2) | C33—C34A | 1.504 (6) |
N2—H112 | 0.95 (3) | C33—H33A | 0.95 (5) |
C6—O4 | 1.3678 (17) | C33—H33B | 1.09 (3) |
C6—C7 | 1.434 (2) | C34B—C39B | 1.370 (4) |
O4—H104 | 0.95 (3) | C34B—C35B | 1.371 (4) |
C7—C8 | 1.420 (2) | C35B—C36B | 1.370 (4) |
O7—C17 | 1.283 (2) | C35B—H35B | 0.9300 |
C8—C22 | 1.405 (2) | C36B—C37B | 1.368 (4) |
C8—C9 | 1.460 (2) | C36B—H36B | 0.9300 |
O8—C16 | 1.3716 (18) | C37B—C38B | 1.369 (4) |
O8—H108 | 0.96 (3) | C37B—H37B | 0.9300 |
C9—C10 | 1.419 (2) | C38B—C39B | 1.366 (4) |
C11—C12 | 1.381 (2) | C38B—H38B | 0.9300 |
C11—C19 | 1.4243 (19) | C39B—H39B | 0.9300 |
C12—C13 | 1.406 (2) | C40—C41 | 1.504 (3) |
C13—C14 | 1.381 (2) | C40—H40A | 0.99 (2) |
C13—C26 | 1.505 (2) | C40—H40B | 0.96 (2) |
C14—C20 | 1.402 (2) | C41—C42 | 1.507 (3) |
C14—H14 | 0.98 (2) | C41—H41A | 0.98 (2) |
C15—C16 | 1.350 (2) | C41—H41B | 0.98 (2) |
C15—C20 | 1.465 (2) | C42—C43 | 1.510 (3) |
C15—C28 | 1.522 (2) | C42—H42A | 0.99 (3) |
C16—C17 | 1.442 (2) | C42—H42B | 0.95 (3) |
C17—C18 | 1.421 (2) | C43—C48 | 1.384 (3) |
C18—C27 | 1.414 (2) | C43—C44 | 1.386 (3) |
C18—C19 | 1.456 (2) | C44—C45 | 1.387 (3) |
C19—C20 | 1.425 (2) | C44—H44 | 1.00 (2) |
C21—H21A | 1.042 (12) | C45—C46 | 1.353 (4) |
C21—H21B | 1.043 (12) | C45—H45 | 1.06 (3) |
C21—H21C | 1.043 (12) | C46—C47 | 1.374 (4) |
C21—H21D | 1.042 (12) | C46—H46 | 1.03 (3) |
C21—H21E | 1.044 (12) | C47—C48 | 1.387 (4) |
C21—H21F | 1.042 (12) | C47—H47 | 1.05 (3) |
C22—H22 | 1.038 (18) | C48—H48 | 0.96 (3) |
C23—C25 | 1.515 (4) | C34A—C39A | 1.373 (4) |
C23—C24 | 1.538 (3) | C34A—C35A | 1.374 (4) |
C23—H23 | 0.94 (2) | C35A—C36A | 1.365 (4) |
C24—H24A | 0.9600 | C35A—H35A | 0.9300 |
C24—H24B | 0.9600 | C36A—C37A | 1.368 (4) |
C24—H24C | 0.9600 | C36A—H36A | 0.9300 |
C25—H25A | 0.9600 | C37A—C38A | 1.370 (4) |
C25—H25B | 0.9600 | C37A—H37A | 0.9300 |
C25—H25C | 0.9600 | C38A—C39A | 1.373 (4) |
C26—H26A | 1.042 (12) | C38A—H38A | 0.9300 |
C26—H26B | 1.041 (12) | C39A—H39A | 0.9300 |
C26—H26C | 1.040 (12) | ||
C1—O1—H101 | 111.9 (16) | H26B—C26—H26F | 140 (4) |
O1—C1—C2 | 119.43 (12) | H26C—C26—H26F | 36 (3) |
O1—C1—C9 | 116.96 (13) | H26D—C26—H26F | 108.5 (16) |
C2—C1—C9 | 123.61 (14) | C13—C26—H26E | 114 (3) |
C1—C2—C3 | 118.94 (13) | H26A—C26—H26E | 35 (3) |
C1—C2—C12 | 120.05 (14) | H26B—C26—H26E | 74 (3) |
C3—C2—C12 | 120.99 (13) | H26C—C26—H26E | 128 (4) |
C22—N1—C31 | 122.98 (16) | H26D—C26—H26E | 108.5 (16) |
C22—N1—H111 | 113.2 (13) | H26F—C26—H26E | 109.3 (16) |
C31—N1—H111 | 123.7 (13) | N2—C27—C18 | 124.42 (14) |
C4—C3—C2 | 118.63 (14) | N2—C27—H27 | 117.1 (11) |
C4—C3—C21 | 121.34 (16) | C18—C27—H27 | 118.5 (11) |
C2—C3—C21 | 120.03 (15) | C30—C28—C15 | 109.87 (19) |
C3—C4—C10 | 123.33 (16) | C30—C28—C29 | 110.83 (19) |
C3—C4—H4 | 116.0 (11) | C15—C28—C29 | 115.30 (19) |
C10—C4—H4 | 120.7 (11) | C30—C28—H28 | 110.9 (12) |
C11—O5—H105 | 112.0 (15) | C15—C28—H28 | 108.0 (12) |
C6—C5—C10 | 118.20 (14) | C29—C28—H28 | 101.6 (13) |
C6—C5—C23 | 120.59 (14) | C28—C29—H29A | 109.5 |
C10—C5—C23 | 121.11 (15) | C28—C29—H29B | 109.5 |
C27—N2—C40 | 124.94 (15) | H29A—C29—H29B | 109.5 |
C27—N2—H112 | 113.8 (16) | C28—C29—H29C | 109.5 |
C40—N2—H112 | 121.2 (15) | H29A—C29—H29C | 109.5 |
C5—C6—O4 | 122.18 (16) | H29B—C29—H29C | 109.5 |
C5—C6—C7 | 123.55 (13) | C28—C30—H30A | 109.5 |
O4—C6—C7 | 114.26 (15) | C28—C30—H30B | 109.5 |
C6—O4—H104 | 98.5 (19) | H30A—C30—H30B | 109.5 |
O3—C7—C8 | 123.73 (15) | C28—C30—H30C | 109.5 |
O3—C7—C6 | 116.67 (13) | H30A—C30—H30C | 109.5 |
C8—C7—C6 | 119.58 (14) | H30B—C30—H30C | 109.5 |
C22—C8—C7 | 117.29 (14) | N1—C31—C32 | 112.3 (2) |
C22—C8—C9 | 124.23 (13) | N1—C31—H31A | 107.9 (13) |
C7—C8—C9 | 118.41 (14) | C32—C31—H31A | 111.0 (13) |
C16—O8—H108 | 101 (2) | N1—C31—H31B | 110.3 (16) |
C1—C9—C10 | 116.68 (13) | C32—C31—H31B | 107.2 (16) |
C1—C9—C8 | 123.72 (13) | H31A—C31—H31B | 108.0 (19) |
C10—C9—C8 | 119.59 (12) | C31—C32—C33 | 114.1 (3) |
C4—C10—C9 | 118.75 (13) | C31—C32—H32A | 113 (2) |
C4—C10—C5 | 120.62 (14) | C33—C32—H32A | 111 (2) |
C9—C10—C5 | 120.62 (14) | C31—C32—H32B | 104 (3) |
O5—C11—C12 | 119.93 (13) | C33—C32—H32B | 109 (3) |
O5—C11—C19 | 116.67 (13) | H32A—C32—H32B | 104 (3) |
C12—C11—C19 | 123.40 (14) | C34B—C33—C34A | 9.2 (6) |
C11—C12—C13 | 119.29 (13) | C34B—C33—C32 | 116.8 (3) |
C11—C12—C2 | 119.75 (13) | C34A—C33—C32 | 112.0 (3) |
C13—C12—C2 | 120.92 (13) | C34B—C33—H33A | 116 (3) |
C14—C13—C12 | 118.49 (15) | C34A—C33—H33A | 113 (3) |
C14—C13—C26 | 120.62 (16) | C32—C33—H33A | 113 (3) |
C12—C13—C26 | 120.89 (14) | C34B—C33—H33B | 94.7 (17) |
C13—C14—C20 | 123.26 (16) | C34A—C33—H33B | 103.8 (16) |
C13—C14—H14 | 117.3 (12) | C32—C33—H33B | 103.1 (16) |
C20—C14—H14 | 119.5 (12) | H33A—C33—H33B | 111 (3) |
C16—C15—C20 | 117.88 (15) | C39B—C34B—C35B | 120.3 (9) |
C16—C15—C28 | 120.92 (14) | C39B—C34B—C33 | 117.5 (8) |
C20—C15—C28 | 121.10 (15) | C35B—C34B—C33 | 122.2 (8) |
C15—C16—O8 | 122.36 (15) | C36B—C35B—C34B | 122.9 (11) |
C15—C16—C17 | 123.86 (14) | C36B—C35B—H35B | 118.5 |
O8—C16—C17 | 113.78 (15) | C34B—C35B—H35B | 118.5 |
O7—C17—C18 | 123.72 (15) | C37B—C36B—C35B | 115.8 (12) |
O7—C17—C16 | 116.81 (14) | C37B—C36B—H36B | 122.1 |
C18—C17—C16 | 119.46 (14) | C35B—C36B—H36B | 122.1 |
C27—C18—C17 | 116.75 (14) | C36B—C37B—C38B | 122.0 (13) |
C27—C18—C19 | 125.01 (13) | C36B—C37B—H37B | 119.0 |
C17—C18—C19 | 118.24 (14) | C38B—C37B—H37B | 119.0 |
C11—C19—C20 | 116.44 (13) | C39B—C38B—C37B | 121.5 (12) |
C11—C19—C18 | 123.53 (13) | C39B—C38B—H38B | 119.2 |
C20—C19—C18 | 120.02 (12) | C37B—C38B—H38B | 119.2 |
C14—C20—C19 | 119.08 (13) | C38B—C39B—C34B | 117.4 (11) |
C14—C20—C15 | 120.52 (14) | C38B—C39B—H39B | 121.3 |
C19—C20—C15 | 120.41 (14) | C34B—C39B—H39B | 121.3 |
C3—C21—H21A | 112.5 (17) | N2—C40—C41 | 110.32 (15) |
C3—C21—H21B | 111.3 (16) | N2—C40—H40A | 109.9 (13) |
H21A—C21—H21B | 108.4 (13) | C41—C40—H40A | 111.3 (13) |
C3—C21—H21C | 106.7 (16) | N2—C40—H40B | 109.5 (13) |
H21A—C21—H21C | 109.1 (14) | C41—C40—H40B | 113.2 (13) |
H21B—C21—H21C | 108.9 (14) | H40A—C40—H40B | 102.4 (18) |
C3—C21—H21D | 119 (4) | C40—C41—C42 | 112.57 (16) |
H21A—C21—H21D | 128 (4) | C40—C41—H41A | 106.0 (13) |
H21B—C21—H21D | 50 (3) | C42—C41—H41A | 111.0 (13) |
H21C—C21—H21D | 59 (3) | C40—C41—H41B | 106.5 (13) |
C3—C21—H21E | 99 (4) | C42—C41—H41B | 115.0 (13) |
H21A—C21—H21E | 59 (4) | H41A—C41—H41B | 105.1 (19) |
H21B—C21—H21E | 61 (4) | C41—C42—C43 | 115.74 (17) |
H21C—C21—H21E | 154 (4) | C41—C42—H42A | 107.5 (15) |
H21D—C21—H21E | 108.5 (17) | C43—C42—H42A | 110.6 (15) |
C3—C21—H21F | 112 (4) | C41—C42—H42B | 108.8 (15) |
H21A—C21—H21F | 50 (4) | C43—C42—H42B | 110.3 (15) |
H21B—C21—H21F | 137 (4) | H42A—C42—H42B | 103 (2) |
H21C—C21—H21F | 62 (4) | C48—C43—C44 | 116.8 (2) |
H21D—C21—H21F | 109.1 (17) | C48—C43—C42 | 120.00 (19) |
H21E—C21—H21F | 108.4 (17) | C44—C43—C42 | 123.11 (17) |
N1—C22—C8 | 124.54 (15) | C43—C44—C45 | 121.8 (2) |
N1—C22—H22 | 115.8 (10) | C43—C44—H44 | 119.0 (14) |
C8—C22—H22 | 119.7 (10) | C45—C44—H44 | 119.2 (14) |
C25—C23—C5 | 110.0 (2) | C46—C45—C44 | 120.3 (3) |
C25—C23—C24 | 111.4 (2) | C46—C45—H45 | 119.9 (16) |
C5—C23—C24 | 114.98 (19) | C44—C45—H45 | 119.7 (16) |
C25—C23—H23 | 108.7 (13) | C45—C46—C47 | 119.4 (2) |
C5—C23—H23 | 106.7 (13) | C45—C46—H46 | 121.4 (18) |
C24—C23—H23 | 104.7 (14) | C47—C46—H46 | 119.2 (18) |
C23—C24—H24A | 109.5 | C46—C47—C48 | 120.5 (3) |
C23—C24—H24B | 109.5 | C46—C47—H47 | 117.6 (18) |
H24A—C24—H24B | 109.5 | C48—C47—H47 | 121.6 (18) |
C23—C24—H24C | 109.5 | C43—C48—C47 | 121.2 (3) |
H24A—C24—H24C | 109.5 | C43—C48—H48 | 118.5 (19) |
H24B—C24—H24C | 109.5 | C47—C48—H48 | 120.3 (19) |
C23—C25—H25A | 109.5 | C39A—C34A—C35A | 116.8 (5) |
C23—C25—H25B | 109.5 | C39A—C34A—C33 | 124.5 (5) |
H25A—C25—H25B | 109.5 | C35A—C34A—C33 | 118.7 (5) |
C23—C25—H25C | 109.5 | C36A—C35A—C34A | 123.0 (6) |
H25A—C25—H25C | 109.5 | C36A—C35A—H35A | 118.5 |
H25B—C25—H25C | 109.5 | C34A—C35A—H35A | 118.5 |
C13—C26—H26A | 109 (2) | C35A—C36A—C37A | 118.4 (6) |
C13—C26—H26B | 107 (2) | C35A—C36A—H36A | 120.8 |
H26A—C26—H26B | 108.7 (15) | C37A—C36A—H36A | 120.8 |
C13—C26—H26C | 114 (2) | C36A—C37A—C38A | 120.8 (7) |
H26A—C26—H26C | 109.3 (15) | C36A—C37A—H37A | 119.6 |
H26B—C26—H26C | 109.3 (15) | C38A—C37A—H37A | 119.6 |
C13—C26—H26D | 108 (3) | C37A—C38A—C39A | 119.1 (7) |
H26A—C26—H26D | 138 (4) | C37A—C38A—H38A | 120.5 |
H26B—C26—H26D | 40 (3) | C39A—C38A—H38A | 120.5 |
H26C—C26—H26D | 73 (3) | C38A—C39A—C34A | 121.9 (6) |
C13—C26—H26F | 108 (3) | C38A—C39A—H39A | 119.1 |
H26A—C26—H26F | 79 (3) | C34A—C39A—H39A | 119.1 |
O1—C1—C2—C3 | 177.23 (14) | C27—C18—C19—C11 | −1.8 (3) |
C9—C1—C2—C3 | −2.8 (2) | C17—C18—C19—C11 | 177.48 (16) |
O1—C1—C2—C12 | −4.6 (2) | C27—C18—C19—C20 | 179.54 (15) |
C9—C1—C2—C12 | 175.40 (14) | C17—C18—C19—C20 | −1.2 (2) |
C1—C2—C3—C4 | 0.8 (2) | C13—C14—C20—C19 | −0.7 (3) |
C12—C2—C3—C4 | −177.33 (15) | C13—C14—C20—C15 | 178.69 (18) |
C1—C2—C3—C21 | −179.62 (17) | C11—C19—C20—C14 | −1.2 (2) |
C12—C2—C3—C21 | 2.2 (2) | C18—C19—C20—C14 | 177.58 (15) |
C2—C3—C4—C10 | 0.7 (3) | C11—C19—C20—C15 | 179.46 (15) |
C21—C3—C4—C10 | −178.81 (17) | C18—C19—C20—C15 | −1.8 (2) |
C10—C5—C6—O4 | 176.00 (16) | C16—C15—C20—C14 | −175.15 (18) |
C23—C5—C6—O4 | −0.3 (3) | C28—C15—C20—C14 | 1.4 (3) |
C10—C5—C6—C7 | −2.6 (3) | C16—C15—C20—C19 | 4.2 (3) |
C23—C5—C6—C7 | −178.96 (17) | C28—C15—C20—C19 | −179.17 (17) |
C5—C6—C7—O3 | −179.57 (16) | C31—N1—C22—C8 | −174.92 (17) |
O4—C6—C7—O3 | 1.7 (2) | C7—C8—C22—N1 | −1.1 (2) |
C5—C6—C7—C8 | 1.7 (3) | C9—C8—C22—N1 | 175.90 (15) |
O4—C6—C7—C8 | −177.03 (15) | C6—C5—C23—C25 | 79.4 (2) |
O3—C7—C8—C22 | −1.8 (2) | C10—C5—C23—C25 | −96.9 (2) |
C6—C7—C8—C22 | 176.82 (14) | C6—C5—C23—C24 | −47.3 (3) |
O3—C7—C8—C9 | −179.06 (14) | C10—C5—C23—C24 | 136.5 (2) |
C6—C7—C8—C9 | −0.4 (2) | C40—N2—C27—C18 | −179.68 (18) |
O1—C1—C9—C10 | −177.00 (13) | C17—C18—C27—N2 | −0.3 (3) |
C2—C1—C9—C10 | 3.0 (2) | C19—C18—C27—N2 | 179.05 (16) |
O1—C1—C9—C8 | 4.4 (2) | C16—C15—C28—C30 | 84.0 (2) |
C2—C1—C9—C8 | −175.58 (14) | C20—C15—C28—C30 | −92.5 (2) |
C22—C8—C9—C1 | 1.8 (2) | C16—C15—C28—C29 | −42.1 (3) |
C7—C8—C9—C1 | 178.80 (14) | C20—C15—C28—C29 | 141.4 (2) |
C22—C8—C9—C10 | −176.76 (14) | C22—N1—C31—C32 | 79.2 (3) |
C7—C8—C9—C10 | 0.3 (2) | N1—C31—C32—C33 | −179.3 (3) |
C3—C4—C10—C9 | −0.4 (2) | C31—C32—C33—C34B | −54.8 (7) |
C3—C4—C10—C5 | 178.10 (16) | C31—C32—C33—C34A | −63.5 (5) |
C1—C9—C10—C4 | −1.3 (2) | C34A—C33—C34B—C39B | 171.9 (14) |
C8—C9—C10—C4 | 177.30 (14) | C32—C33—C34B—C39B | 110.8 (6) |
C1—C9—C10—C5 | −179.88 (14) | C34A—C33—C34B—C35B | −8.1 (14) |
C8—C9—C10—C5 | −1.2 (2) | C32—C33—C34B—C35B | −69.2 (6) |
C6—C5—C10—C4 | −176.12 (16) | C39B—C34B—C35B—C36B | −0.04 (14) |
C23—C5—C10—C4 | 0.2 (2) | C33—C34B—C35B—C36B | 179.99 (9) |
C6—C5—C10—C9 | 2.4 (2) | C34B—C35B—C36B—C37B | 0.02 (14) |
C23—C5—C10—C9 | 178.71 (16) | C35B—C36B—C37B—C38B | −0.01 (14) |
O5—C11—C12—C13 | 178.99 (15) | C36B—C37B—C38B—C39B | 0.01 (14) |
C19—C11—C12—C13 | −1.7 (2) | C37B—C38B—C39B—C34B | −0.02 (14) |
O5—C11—C12—C2 | −3.3 (2) | C35B—C34B—C39B—C38B | 0.04 (13) |
C19—C11—C12—C2 | 176.04 (14) | C33—C34B—C39B—C38B | −179.99 (8) |
C1—C2—C12—C11 | 90.18 (19) | C27—N2—C40—C41 | −173.35 (18) |
C3—C2—C12—C11 | −91.68 (19) | N2—C40—C41—C42 | −177.27 (18) |
C1—C2—C12—C13 | −92.2 (2) | C40—C41—C42—C43 | 179.3 (2) |
C3—C2—C12—C13 | 86.0 (2) | C41—C42—C43—C48 | 172.4 (2) |
C11—C12—C13—C14 | −0.3 (3) | C41—C42—C43—C44 | −11.0 (3) |
C2—C12—C13—C14 | −177.96 (16) | C48—C43—C44—C45 | −0.5 (3) |
C11—C12—C13—C26 | 179.44 (18) | C42—C43—C44—C45 | −177.2 (2) |
C2—C12—C13—C26 | 1.8 (3) | C43—C44—C45—C46 | −0.1 (4) |
C12—C13—C14—C20 | 1.5 (3) | C44—C45—C46—C47 | 0.7 (4) |
C26—C13—C14—C20 | −178.3 (2) | C45—C46—C47—C48 | −0.7 (5) |
C20—C15—C16—O8 | 175.71 (18) | C44—C43—C48—C47 | 0.5 (4) |
C28—C15—C16—O8 | −0.9 (3) | C42—C43—C48—C47 | 177.3 (3) |
C20—C15—C16—C17 | −3.8 (3) | C46—C47—C48—C43 | 0.1 (5) |
C28—C15—C16—C17 | 179.64 (19) | C34B—C33—C34A—C39A | 0.2 (14) |
C15—C16—C17—O7 | −177.93 (19) | C32—C33—C34A—C39A | 122.7 (5) |
O8—C16—C17—O7 | 2.6 (3) | C34B—C33—C34A—C35A | −180 (100) |
C15—C16—C17—C18 | 0.8 (3) | C32—C33—C34A—C35A | −57.4 (5) |
O8—C16—C17—C18 | −178.70 (17) | C39A—C34A—C35A—C36A | −0.03 (13) |
O7—C17—C18—C27 | −0.3 (3) | C33—C34A—C35A—C36A | 179.99 (9) |
C16—C17—C18—C27 | −178.90 (16) | C34A—C35A—C36A—C37A | 0.03 (14) |
O7—C17—C18—C19 | −179.61 (17) | C35A—C36A—C37A—C38A | −0.03 (13) |
C16—C17—C18—C19 | 1.7 (3) | C36A—C37A—C38A—C39A | 0.02 (14) |
O5—C11—C19—C20 | −178.27 (14) | C37A—C38A—C39A—C34A | −0.02 (14) |
C12—C11—C19—C20 | 2.4 (2) | C35A—C34A—C39A—C38A | 0.02 (13) |
O5—C11—C19—C18 | 3.0 (2) | C33—C34A—C39A—C38A | 180.00 (8) |
C12—C11—C19—C18 | −176.33 (15) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H101···O7i | 0.82 (2) | 1.99 (2) | 2.617 (2) | 133 (2) |
N1—H111···O3 | 0.96 (2) | 1.74 (2) | 2.540 (2) | 139 (2) |
O4—H104···O5ii | 0.95 (3) | 2.42 (3) | 3.225 (2) | 142 (3) |
O4—H104···O3 | 0.95 (3) | 1.87 (3) | 2.576 (2) | 128 (3) |
O5—H105···O3ii | 0.86 (2) | 1.99 (2) | 2.654 (2) | 134 (2) |
N2—H112···O7 | 0.95 (3) | 1.73 (3) | 2.524 (2) | 138 (2) |
O8—H108···O7 | 0.96 (3) | 1.91 (3) | 2.577 (2) | 124 (3) |
O8—H108···O1iii | 0.96 (3) | 2.19 (4) | 3.036 (2) | 146 (3) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y, −z+1; (iii) x, −y+1/2, z+1/2. |
C48H52N2O6 | F(000) = 1608 |
Mr = 752.92 | Dx = 1.234 Mg m−3 Dm = 1.19 Mg m−3 Dm measured by flotation in aqueous KI |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 33430 reflections |
a = 11.9559 (9) Å | θ = 2.2–27.4° |
b = 29.079 (2) Å | µ = 0.08 mm−1 |
c = 11.6918 (9) Å | T = 120 K |
β = 94.207 (1)° | Diamond, yellow |
V = 4053.9 (5) Å3 | 0.60 × 0.40 × 0.30 mm |
Z = 4 |
Bruker APEXII CCD area-detector diffractometer | 9192 independent reflections |
Radiation source: fine-focus sealed tube | 7917 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
φ and ω scans | θmax = 27.5°, θmin = 2.2° |
Absorption correction: empirical (using intensity measurements) (SADABS; Bruker, 2009) | h = −15→15 |
Tmin = 0.953, Tmax = 0.976 | k = −37→37 |
58753 measured reflections | l = −15→15 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0623P)2 + 1.8081P] where P = (Fo2 + 2Fc2)/3 |
9192 reflections | (Δ/σ)max = 0.001 |
705 parameters | Δρmax = 0.78 e Å−3 |
73 restraints | Δρmin = −0.37 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 | ||
O1 | 0.02818 (8) | 0.10415 (3) | 0.41306 (8) | 0.02308 (19) | |
H101 | 0.0321 (17) | 0.1332 (8) | 0.4181 (17) | 0.049 (5)* | |
C1 | 0.11754 (10) | 0.08263 (4) | 0.46898 (10) | 0.0180 (2) | |
N1 | −0.09397 (9) | 0.00460 (4) | 0.21931 (9) | 0.0242 (2) | |
H111 | −0.0777 (15) | −0.0266 (7) | 0.2155 (15) | 0.039 (5)* | |
C2 | 0.19342 (10) | 0.10806 (4) | 0.53868 (10) | 0.0191 (2) | |
N2 | −0.08040 (9) | 0.24140 (4) | 0.88295 (9) | 0.0230 (2) | |
H112 | −0.0735 (17) | 0.2724 (8) | 0.8884 (18) | 0.052 (6)* | |
O3 | 0.01624 (8) | −0.06586 (3) | 0.28800 (8) | 0.0264 (2) | |
C3 | 0.28144 (10) | 0.08517 (4) | 0.60136 (11) | 0.0215 (2) | |
O4 | 0.17734 (9) | −0.10675 (3) | 0.40633 (9) | 0.0291 (2) | |
H104 | 0.1253 (18) | −0.1124 (7) | 0.3548 (19) | 0.049 (6)* | |
C4 | 0.29041 (10) | 0.03803 (4) | 0.59030 (11) | 0.0215 (2) | |
H4 | 0.3522 (14) | 0.0225 (6) | 0.6354 (14) | 0.027 (4)* | |
O5 | 0.05678 (8) | 0.15098 (3) | 0.69249 (8) | 0.0255 (2) | |
H105 | 0.0657 (16) | 0.1223 (7) | 0.6767 (17) | 0.045 (5)* | |
C5 | 0.23147 (10) | −0.03789 (4) | 0.50624 (11) | 0.0208 (2) | |
C6 | 0.16359 (11) | −0.06104 (4) | 0.42796 (11) | 0.0217 (2) | |
O7 | −0.01550 (9) | 0.31792 (3) | 0.81195 (9) | 0.0323 (2) | |
C7 | 0.07332 (10) | −0.03959 (4) | 0.35899 (10) | 0.0204 (2) | |
C8 | 0.05371 (10) | 0.00830 (4) | 0.37107 (10) | 0.0187 (2) | |
O8 | 0.09452 (9) | 0.37003 (3) | 0.68062 (9) | 0.0318 (2) | |
H108 | 0.0551 (17) | 0.3721 (7) | 0.7403 (19) | 0.051 (6)* | |
C9 | 0.12733 (10) | 0.03445 (4) | 0.45210 (10) | 0.0172 (2) | |
C10 | 0.21612 (10) | 0.01168 (4) | 0.51679 (10) | 0.0186 (2) | |
C11 | 0.11489 (10) | 0.17878 (4) | 0.62356 (10) | 0.0190 (2) | |
C12 | 0.18174 (10) | 0.15936 (4) | 0.54448 (10) | 0.0195 (2) | |
C13 | 0.23984 (11) | 0.18842 (4) | 0.47261 (11) | 0.0223 (3) | |
C14 | 0.22792 (11) | 0.23547 (4) | 0.48321 (11) | 0.0221 (2) | |
H14 | 0.2663 (13) | 0.2543 (5) | 0.4313 (13) | 0.024 (4)* | |
C15 | 0.15550 (11) | 0.30600 (4) | 0.57399 (11) | 0.0222 (2) | |
C16 | 0.09885 (11) | 0.32380 (4) | 0.66003 (12) | 0.0238 (3) | |
C17 | 0.03806 (11) | 0.29603 (4) | 0.73742 (11) | 0.0232 (3) | |
C18 | 0.03867 (10) | 0.24748 (4) | 0.72660 (10) | 0.0195 (2) | |
C19 | 0.10394 (10) | 0.22699 (4) | 0.63909 (10) | 0.0184 (2) | |
C20 | 0.16209 (10) | 0.25592 (4) | 0.56460 (10) | 0.0198 (2) | |
C21 | 0.36362 (12) | 0.11190 (5) | 0.67936 (13) | 0.0283 (3) | |
H21C | 0.4044 (16) | 0.1351 (7) | 0.6338 (16) | 0.042 (5)* | |
H21B | 0.3248 (16) | 0.1303 (7) | 0.7374 (17) | 0.045 (5)* | |
H21A | 0.4211 (16) | 0.0913 (7) | 0.7185 (17) | 0.045 (5)* | |
C22 | −0.03333 (10) | 0.02768 (4) | 0.29809 (11) | 0.0210 (2) | |
H22A | −0.0519 (13) | 0.0603 (5) | 0.3034 (13) | 0.024 (4)* | |
C23 | 0.32598 (12) | −0.06257 (4) | 0.57501 (12) | 0.0277 (3) | |
H23 | 0.3520 (14) | −0.0429 (6) | 0.6420 (15) | 0.035 (4)* | |
C24 | 0.42661 (14) | −0.06743 (7) | 0.50281 (18) | 0.0454 (4) | |
H24C | 0.4507 (19) | −0.0365 (9) | 0.473 (2) | 0.068 (7)* | |
H24B | 0.4071 (17) | −0.0869 (8) | 0.4376 (19) | 0.055 (6)* | |
H24A | 0.4906 (18) | −0.0813 (8) | 0.5497 (18) | 0.056 (6)* | |
C25 | 0.29445 (16) | −0.10921 (5) | 0.62566 (15) | 0.0383 (4) | |
H25C | 0.3507 (17) | −0.1183 (7) | 0.6876 (17) | 0.048 (5)* | |
H25B | 0.2937 (17) | −0.1337 (7) | 0.5698 (18) | 0.052 (6)* | |
H25A | 0.2195 (19) | −0.1086 (7) | 0.6600 (19) | 0.057 (6)* | |
C26 | 0.31375 (13) | 0.16848 (5) | 0.38591 (13) | 0.0307 (3) | |
H26C | 0.3335 (15) | 0.1919 (7) | 0.3289 (16) | 0.041 (5)* | |
H26B | 0.2746 (17) | 0.1426 (7) | 0.3416 (17) | 0.050 (5)* | |
H26A | 0.3829 (18) | 0.1567 (7) | 0.4239 (18) | 0.055 (6)* | |
C27 | −0.02427 (10) | 0.22227 (4) | 0.80412 (11) | 0.0206 (2) | |
H27 | −0.0280 (13) | 0.1893 (6) | 0.8002 (13) | 0.027 (4)* | |
C28 | 0.21666 (13) | 0.33729 (4) | 0.49441 (12) | 0.0285 (3) | |
H28 | 0.2270 (14) | 0.3200 (6) | 0.4229 (15) | 0.032 (4)* | |
C29 | 0.15283 (15) | 0.38114 (5) | 0.45508 (14) | 0.0357 (3) | |
H29B | 0.1543 (14) | 0.4049 (6) | 0.5159 (15) | 0.036 (4)* | |
H29C | 0.1874 (15) | 0.3946 (6) | 0.3881 (16) | 0.037 (5)* | |
H29A | 0.0705 (18) | 0.3745 (7) | 0.4304 (17) | 0.050 (5)* | |
C30 | 0.33178 (14) | 0.34981 (6) | 0.55088 (16) | 0.0390 (4) | |
H30C | 0.3254 (14) | 0.3668 (6) | 0.6238 (16) | 0.036 (4)* | |
H30B | 0.3787 (17) | 0.3223 (7) | 0.5672 (17) | 0.048 (5)* | |
H30A | 0.3730 (16) | 0.3689 (7) | 0.4997 (17) | 0.047 (5)* | |
C31 | −0.17656 (12) | 0.02684 (5) | 0.13941 (12) | 0.0280 (3) | |
H31B | −0.2304 (14) | 0.0025 (6) | 0.1090 (14) | 0.032 (4)* | |
H31A | −0.2193 (15) | 0.0498 (6) | 0.1822 (16) | 0.040 (5)* | |
C32 | −0.12169 (14) | 0.05076 (6) | 0.04222 (15) | 0.0399 (4) | |
H32B | −0.0765 (18) | 0.0269 (8) | 0.0009 (18) | 0.055 (6)* | |
H32A | −0.0663 (18) | 0.0738 (8) | 0.0753 (19) | 0.060 (6)* | |
C33 | −0.20658 (16) | 0.07359 (6) | −0.04442 (16) | 0.0443 (4) | |
H33B | −0.2473 (16) | 0.0960 (7) | −0.0011 (17) | 0.044 (5)* | |
H33A | −0.1624 (19) | 0.0901 (8) | −0.105 (2) | 0.063 (6)* | |
C34 | −0.28915 (14) | 0.04002 (6) | −0.10122 (13) | 0.0380 (3) | |
C35 | −0.24830 (19) | 0.00324 (7) | −0.16325 (15) | 0.0528 (4) | |
H35 | −0.158 (2) | 0.0005 (9) | −0.170 (2) | 0.090 (8)* | |
C36 | −0.3173 (2) | −0.02896 (9) | −0.21598 (17) | 0.0697 (6) | |
H36 | −0.2870 | −0.0536 | −0.2572 | 0.084* | |
C37 | −0.4283 (3) | −0.02542 (10) | −0.2090 (2) | 0.0772 (6) | |
H37 | −0.487 (3) | −0.0475 (11) | −0.247 (3) | 0.116 (11)* | |
C38 | −0.47539 (18) | 0.00983 (10) | −0.1487 (2) | 0.0757 (6) | |
H38 | −0.5543 | 0.0116 | −0.1441 | 0.091* | |
C39 | −0.40283 (16) | 0.04364 (8) | −0.0932 (2) | 0.0581 (5) | |
H39 | −0.4242 (14) | 0.0672 (6) | −0.0457 (15) | 0.029 (4)* | |
C40 | −0.14515 (12) | 0.21628 (4) | 0.96384 (11) | 0.0243 (3) | |
H40B | −0.0941 (14) | 0.1972 (6) | 1.0133 (14) | 0.029 (4)* | |
H40A | −0.1989 (14) | 0.1961 (6) | 0.9195 (14) | 0.030 (4)* | |
C41 | −0.20643 (11) | 0.25041 (4) | 1.03490 (11) | 0.0229 (3) | |
H41B | −0.2566 (13) | 0.2683 (5) | 0.9832 (13) | 0.022 (4)* | |
H41A | −0.1514 (14) | 0.2712 (6) | 1.0731 (14) | 0.028 (4)* | |
C42 | −0.27215 (12) | 0.22669 (5) | 1.12437 (12) | 0.0267 (3) | |
H42B | −0.2188 (14) | 0.2081 (6) | 1.1742 (15) | 0.030 (4)* | |
H42A | −0.3255 (15) | 0.2050 (6) | 1.0846 (15) | 0.034 (4)* | |
C43 | −0.33502 (11) | 0.25879 (5) | 1.19907 (11) | 0.0240 (3) | |
C44 | −0.40572 (12) | 0.24050 (5) | 1.27734 (12) | 0.0308 (3) | |
H44 | −0.4172 (15) | 0.2069 (7) | 1.2818 (16) | 0.041 (5)* | |
C45 | −0.46126 (13) | 0.26897 (6) | 1.35000 (14) | 0.0371 (3) | |
H45 | −0.5099 (18) | 0.2555 (7) | 1.4058 (18) | 0.053 (6)* | |
C46 | −0.44767 (13) | 0.31624 (6) | 1.34521 (13) | 0.0356 (3) | |
H46 | −0.4847 (16) | 0.3378 (7) | 1.3958 (16) | 0.044 (5)* | |
C47 | −0.37911 (13) | 0.33500 (5) | 1.26738 (12) | 0.0320 (3) | |
H47 | −0.3676 (15) | 0.3682 (7) | 1.2635 (16) | 0.040 (5)* | |
C48 | −0.32328 (12) | 0.30647 (5) | 1.19450 (12) | 0.0271 (3) | |
H48 | −0.2745 (14) | 0.3207 (6) | 1.1390 (14) | 0.031 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0264 (5) | 0.0124 (4) | 0.0298 (5) | 0.0011 (3) | −0.0021 (4) | 0.0002 (3) |
C1 | 0.0203 (5) | 0.0149 (5) | 0.0192 (5) | 0.0004 (4) | 0.0050 (4) | 0.0009 (4) |
N1 | 0.0275 (6) | 0.0205 (5) | 0.0241 (5) | −0.0034 (4) | −0.0017 (4) | 0.0004 (4) |
C2 | 0.0215 (6) | 0.0140 (5) | 0.0223 (6) | −0.0013 (4) | 0.0059 (4) | −0.0029 (4) |
N2 | 0.0268 (5) | 0.0194 (5) | 0.0235 (5) | −0.0045 (4) | 0.0067 (4) | −0.0044 (4) |
O3 | 0.0360 (5) | 0.0161 (4) | 0.0264 (5) | −0.0049 (4) | −0.0013 (4) | −0.0027 (3) |
C3 | 0.0216 (6) | 0.0190 (6) | 0.0242 (6) | −0.0019 (4) | 0.0029 (5) | −0.0037 (5) |
O4 | 0.0363 (5) | 0.0137 (4) | 0.0364 (6) | 0.0030 (4) | −0.0025 (4) | −0.0060 (4) |
C4 | 0.0204 (6) | 0.0196 (6) | 0.0246 (6) | 0.0013 (4) | 0.0015 (5) | −0.0020 (5) |
O5 | 0.0368 (5) | 0.0132 (4) | 0.0279 (5) | −0.0031 (4) | 0.0123 (4) | −0.0024 (3) |
C5 | 0.0227 (6) | 0.0160 (5) | 0.0239 (6) | 0.0020 (4) | 0.0042 (5) | −0.0003 (4) |
C6 | 0.0274 (6) | 0.0133 (5) | 0.0251 (6) | 0.0010 (4) | 0.0058 (5) | −0.0010 (4) |
O7 | 0.0404 (6) | 0.0183 (4) | 0.0407 (6) | −0.0048 (4) | 0.0212 (5) | −0.0094 (4) |
C7 | 0.0250 (6) | 0.0165 (5) | 0.0201 (6) | −0.0036 (4) | 0.0037 (5) | −0.0008 (4) |
C8 | 0.0219 (6) | 0.0149 (5) | 0.0196 (6) | −0.0027 (4) | 0.0041 (4) | −0.0001 (4) |
O8 | 0.0475 (6) | 0.0132 (4) | 0.0370 (6) | −0.0021 (4) | 0.0192 (5) | −0.0042 (4) |
C9 | 0.0195 (5) | 0.0144 (5) | 0.0182 (5) | −0.0016 (4) | 0.0050 (4) | −0.0009 (4) |
C10 | 0.0203 (6) | 0.0157 (5) | 0.0204 (6) | −0.0001 (4) | 0.0053 (4) | −0.0014 (4) |
C11 | 0.0213 (6) | 0.0155 (5) | 0.0202 (6) | −0.0026 (4) | 0.0005 (4) | −0.0008 (4) |
C12 | 0.0214 (6) | 0.0144 (5) | 0.0224 (6) | −0.0018 (4) | 0.0008 (4) | −0.0033 (4) |
C13 | 0.0244 (6) | 0.0185 (6) | 0.0248 (6) | −0.0020 (4) | 0.0060 (5) | −0.0041 (5) |
C14 | 0.0256 (6) | 0.0173 (6) | 0.0242 (6) | −0.0038 (4) | 0.0070 (5) | −0.0014 (5) |
C15 | 0.0271 (6) | 0.0155 (5) | 0.0244 (6) | −0.0025 (4) | 0.0043 (5) | −0.0008 (4) |
C16 | 0.0289 (6) | 0.0135 (5) | 0.0294 (6) | −0.0018 (5) | 0.0060 (5) | −0.0026 (5) |
C17 | 0.0253 (6) | 0.0181 (6) | 0.0268 (6) | −0.0020 (5) | 0.0065 (5) | −0.0048 (5) |
C18 | 0.0211 (6) | 0.0165 (5) | 0.0209 (6) | −0.0020 (4) | 0.0016 (5) | −0.0035 (4) |
C19 | 0.0200 (5) | 0.0163 (5) | 0.0188 (5) | −0.0016 (4) | 0.0007 (4) | −0.0026 (4) |
C20 | 0.0219 (6) | 0.0159 (5) | 0.0217 (6) | −0.0017 (4) | 0.0016 (5) | −0.0023 (4) |
C21 | 0.0269 (7) | 0.0225 (6) | 0.0345 (7) | −0.0020 (5) | −0.0043 (6) | −0.0069 (5) |
C22 | 0.0233 (6) | 0.0184 (6) | 0.0215 (6) | −0.0029 (4) | 0.0035 (5) | 0.0005 (4) |
C23 | 0.0296 (7) | 0.0196 (6) | 0.0331 (7) | 0.0060 (5) | −0.0035 (6) | −0.0033 (5) |
C24 | 0.0289 (8) | 0.0463 (10) | 0.0610 (11) | 0.0124 (7) | 0.0042 (8) | −0.0026 (9) |
C25 | 0.0501 (10) | 0.0224 (7) | 0.0408 (9) | 0.0074 (6) | −0.0080 (7) | 0.0040 (6) |
C26 | 0.0368 (8) | 0.0206 (6) | 0.0370 (8) | −0.0027 (5) | 0.0177 (6) | −0.0051 (6) |
C27 | 0.0229 (6) | 0.0178 (6) | 0.0211 (6) | −0.0010 (4) | 0.0012 (5) | −0.0027 (4) |
C28 | 0.0429 (8) | 0.0161 (6) | 0.0283 (7) | −0.0020 (5) | 0.0149 (6) | −0.0012 (5) |
C29 | 0.0555 (10) | 0.0210 (6) | 0.0315 (8) | 0.0011 (6) | 0.0095 (7) | 0.0036 (6) |
C30 | 0.0363 (8) | 0.0314 (8) | 0.0517 (10) | −0.0060 (6) | 0.0201 (7) | 0.0040 (7) |
C31 | 0.0269 (7) | 0.0298 (7) | 0.0266 (7) | −0.0015 (5) | −0.0038 (5) | 0.0004 (5) |
C32 | 0.0348 (8) | 0.0431 (9) | 0.0404 (9) | −0.0101 (7) | −0.0068 (7) | 0.0165 (7) |
C33 | 0.0482 (10) | 0.0379 (8) | 0.0446 (9) | −0.0052 (7) | −0.0105 (8) | 0.0155 (7) |
C34 | 0.0397 (8) | 0.0440 (8) | 0.0290 (7) | −0.0048 (6) | −0.0060 (6) | 0.0165 (6) |
C35 | 0.0672 (12) | 0.0618 (11) | 0.0306 (8) | −0.0115 (9) | 0.0118 (8) | 0.0033 (7) |
C36 | 0.1006 (15) | 0.0733 (14) | 0.0343 (10) | −0.0202 (12) | −0.0013 (10) | −0.0010 (9) |
C37 | 0.0925 (14) | 0.0813 (15) | 0.0522 (13) | −0.0266 (12) | −0.0326 (12) | 0.0200 (10) |
C38 | 0.0378 (10) | 0.0984 (16) | 0.0868 (16) | −0.0083 (9) | −0.0237 (10) | 0.0408 (12) |
C39 | 0.0405 (9) | 0.0657 (12) | 0.0664 (13) | 0.0084 (8) | −0.0078 (9) | 0.0243 (10) |
C40 | 0.0291 (7) | 0.0224 (6) | 0.0224 (6) | −0.0033 (5) | 0.0072 (5) | −0.0015 (5) |
C41 | 0.0236 (6) | 0.0246 (6) | 0.0208 (6) | −0.0014 (5) | 0.0038 (5) | −0.0015 (5) |
C42 | 0.0318 (7) | 0.0246 (6) | 0.0244 (6) | −0.0013 (5) | 0.0078 (5) | −0.0005 (5) |
C43 | 0.0233 (6) | 0.0289 (6) | 0.0199 (6) | 0.0009 (5) | 0.0016 (5) | 0.0006 (5) |
C44 | 0.0302 (7) | 0.0335 (7) | 0.0294 (7) | −0.0010 (6) | 0.0073 (6) | 0.0029 (6) |
C45 | 0.0310 (7) | 0.0496 (9) | 0.0322 (8) | 0.0039 (6) | 0.0118 (6) | 0.0034 (7) |
C46 | 0.0314 (7) | 0.0461 (9) | 0.0299 (7) | 0.0145 (6) | 0.0059 (6) | −0.0035 (6) |
C47 | 0.0349 (7) | 0.0310 (7) | 0.0298 (7) | 0.0085 (6) | 0.0000 (6) | −0.0017 (6) |
C48 | 0.0284 (7) | 0.0283 (7) | 0.0251 (6) | 0.0020 (5) | 0.0041 (5) | 0.0010 (5) |
O1—C1 | 1.3630 (14) | C25—H25C | 0.99 (2) |
O1—H101 | 0.85 (2) | C25—H25B | 0.97 (2) |
C1—C2 | 1.3876 (17) | C25—H25A | 1.01 (2) |
C1—C9 | 1.4210 (15) | C26—H26C | 0.993 (19) |
N1—C22 | 1.3139 (16) | C26—H26B | 1.01 (2) |
N1—C31 | 1.4596 (17) | C26—H26A | 0.97 (2) |
N1—H111 | 0.930 (19) | C27—H27 | 0.962 (16) |
C2—C3 | 1.4051 (17) | C28—C30 | 1.526 (2) |
C2—C12 | 1.5003 (15) | C28—C29 | 1.539 (2) |
N2—C27 | 1.3039 (16) | C28—H28 | 0.991 (17) |
N2—C40 | 1.4610 (16) | C29—H29B | 0.990 (18) |
N2—H112 | 0.91 (2) | C29—H29C | 0.992 (19) |
O3—C7 | 1.2865 (15) | C29—H29A | 1.02 (2) |
C3—C4 | 1.3819 (17) | C30—H30C | 0.993 (18) |
C3—C21 | 1.5065 (17) | C30—H30B | 0.99 (2) |
O4—C6 | 1.3652 (14) | C30—H30A | 0.98 (2) |
O4—H104 | 0.85 (2) | C31—C32 | 1.521 (2) |
C4—C10 | 1.4151 (17) | C31—H31B | 1.004 (17) |
C4—H4 | 0.985 (16) | C31—H31A | 0.997 (19) |
O5—C11 | 1.3665 (14) | C32—C33 | 1.532 (2) |
O5—H105 | 0.86 (2) | C32—H32B | 1.02 (2) |
C5—C6 | 1.3566 (18) | C32—H32A | 1.00 (2) |
C5—C10 | 1.4596 (16) | C33—C34 | 1.507 (2) |
C5—C23 | 1.5182 (17) | C33—H33B | 0.98 (2) |
C6—C7 | 1.4411 (18) | C33—H33A | 1.03 (2) |
O7—C17 | 1.2871 (15) | C34—C39 | 1.373 (3) |
C7—C8 | 1.4209 (16) | C34—C35 | 1.400 (3) |
C8—C22 | 1.4136 (17) | C35—C36 | 1.365 (3) |
C8—C9 | 1.4588 (16) | C35—H35 | 1.09 (3) |
O8—C16 | 1.3674 (14) | C36—C37 | 1.339 (4) |
O8—H108 | 0.87 (2) | C36—H36 | 0.9500 |
C9—C10 | 1.4211 (16) | C37—C38 | 1.387 (4) |
C11—C12 | 1.3859 (17) | C37—H37 | 1.03 (3) |
C11—C19 | 1.4211 (16) | C38—C39 | 1.434 (3) |
C12—C13 | 1.4101 (17) | C38—H38 | 0.9500 |
C13—C14 | 1.3822 (17) | C39—H39 | 0.930 (17) |
C13—C26 | 1.5086 (17) | C40—C41 | 1.5169 (17) |
C14—C20 | 1.4101 (17) | C40—H40B | 0.980 (17) |
C14—H14 | 0.959 (16) | C40—H40A | 0.989 (17) |
C15—C16 | 1.3560 (18) | C41—C42 | 1.5192 (18) |
C15—C20 | 1.4628 (16) | C41—H41B | 0.972 (16) |
C15—C28 | 1.5259 (17) | C41—H41A | 0.977 (17) |
C16—C17 | 1.4476 (17) | C42—C43 | 1.5151 (18) |
C17—C18 | 1.4175 (16) | C42—H42B | 0.992 (17) |
C18—C27 | 1.4230 (17) | C42—H42A | 0.989 (18) |
C18—C19 | 1.4587 (16) | C43—C48 | 1.3949 (19) |
C19—C20 | 1.4278 (16) | C43—C44 | 1.3959 (18) |
C21—H21C | 1.007 (19) | C44—C45 | 1.389 (2) |
C21—H21B | 1.00 (2) | C44—H44 | 0.988 (19) |
C21—H21A | 1.00 (2) | C45—C46 | 1.386 (2) |
C22—H22A | 0.976 (16) | C45—H45 | 0.99 (2) |
C23—C24 | 1.526 (2) | C46—C47 | 1.381 (2) |
C23—C25 | 1.538 (2) | C46—H46 | 0.99 (2) |
C23—H23 | 1.001 (18) | C47—C48 | 1.3939 (19) |
C24—H24C | 1.01 (3) | C47—H47 | 0.98 (2) |
C24—H24B | 0.97 (2) | C48—H48 | 0.994 (17) |
C24—H24A | 0.99 (2) | ||
C1—O1—H101 | 112.7 (14) | C13—C26—H26B | 111.0 (11) |
O1—C1—C2 | 119.53 (10) | H26C—C26—H26B | 106.9 (15) |
O1—C1—C9 | 117.10 (10) | C13—C26—H26A | 110.4 (12) |
C2—C1—C9 | 123.37 (11) | H26C—C26—H26A | 108.2 (16) |
C22—N1—C31 | 122.33 (11) | H26B—C26—H26A | 108.5 (17) |
C22—N1—H111 | 115.2 (11) | N2—C27—C18 | 123.65 (11) |
C31—N1—H111 | 122.4 (11) | N2—C27—H27 | 115.8 (9) |
C1—C2—C3 | 119.10 (10) | C18—C27—H27 | 120.6 (9) |
C1—C2—C12 | 119.82 (11) | C15—C28—C30 | 109.62 (12) |
C3—C2—C12 | 121.07 (11) | C15—C28—C29 | 115.27 (12) |
C27—N2—C40 | 124.67 (11) | C30—C28—C29 | 110.08 (12) |
C27—N2—H112 | 115.2 (13) | C15—C28—H28 | 107.9 (10) |
C40—N2—H112 | 120.0 (13) | C30—C28—H28 | 108.8 (10) |
C4—C3—C2 | 118.78 (11) | C29—C28—H28 | 104.9 (10) |
C4—C3—C21 | 121.11 (12) | C28—C29—H29B | 112.4 (10) |
C2—C3—C21 | 120.11 (11) | C28—C29—H29C | 109.6 (10) |
C6—O4—H104 | 103.1 (14) | H29B—C29—H29C | 107.9 (14) |
C3—C4—C10 | 122.98 (11) | C28—C29—H29A | 111.9 (12) |
C3—C4—H4 | 117.7 (9) | H29B—C29—H29A | 107.5 (15) |
C10—C4—H4 | 119.3 (9) | H29C—C29—H29A | 107.4 (15) |
C11—O5—H105 | 111.7 (13) | C28—C30—H30C | 111.5 (10) |
C6—C5—C10 | 118.32 (11) | C28—C30—H30B | 111.9 (12) |
C6—C5—C23 | 120.52 (11) | H30C—C30—H30B | 108.3 (16) |
C10—C5—C23 | 121.02 (11) | C28—C30—H30A | 110.5 (12) |
C5—C6—O4 | 122.27 (11) | H30C—C30—H30A | 108.5 (15) |
C5—C6—C7 | 123.30 (11) | H30B—C30—H30A | 105.9 (16) |
O4—C6—C7 | 114.41 (11) | N1—C31—C32 | 111.84 (12) |
O3—C7—C8 | 124.24 (11) | N1—C31—H31B | 107.5 (10) |
O3—C7—C6 | 116.35 (11) | C32—C31—H31B | 111.0 (10) |
C8—C7—C6 | 119.40 (11) | N1—C31—H31A | 108.9 (11) |
C22—C8—C7 | 116.75 (11) | C32—C31—H31A | 109.5 (11) |
C22—C8—C9 | 124.52 (10) | H31B—C31—H31A | 108.1 (14) |
C7—C8—C9 | 118.64 (11) | C31—C32—C33 | 113.02 (14) |
C16—O8—H108 | 103.7 (14) | C31—C32—H32B | 108.3 (12) |
C1—C9—C10 | 116.83 (10) | C33—C32—H32B | 109.2 (12) |
C1—C9—C8 | 123.52 (11) | C31—C32—H32A | 109.1 (13) |
C10—C9—C8 | 119.63 (10) | C33—C32—H32A | 110.7 (13) |
C4—C10—C9 | 118.83 (10) | H32B—C32—H32A | 106.2 (17) |
C4—C10—C5 | 120.59 (11) | C34—C33—C32 | 113.05 (14) |
C9—C10—C5 | 120.58 (11) | C34—C33—H33B | 109.0 (12) |
O5—C11—C12 | 119.71 (10) | C32—C33—H33B | 106.1 (11) |
O5—C11—C19 | 116.91 (10) | C34—C33—H33A | 110.6 (13) |
C12—C11—C19 | 123.38 (11) | C32—C33—H33A | 107.9 (13) |
C11—C12—C13 | 119.14 (10) | H33B—C33—H33A | 110.1 (17) |
C11—C12—C2 | 119.70 (10) | C39—C34—C35 | 118.57 (19) |
C13—C12—C2 | 121.15 (11) | C39—C34—C33 | 122.68 (19) |
C14—C13—C12 | 118.76 (11) | C35—C34—C33 | 118.74 (16) |
C14—C13—C26 | 120.67 (11) | C36—C35—C34 | 122.4 (2) |
C12—C13—C26 | 120.57 (11) | C36—C35—H35 | 118.9 (15) |
C13—C14—C20 | 122.98 (11) | C34—C35—H35 | 118.7 (15) |
C13—C14—H14 | 116.8 (9) | C37—C36—C35 | 119.2 (3) |
C20—C14—H14 | 120.2 (9) | C37—C36—H36 | 120.4 |
C16—C15—C20 | 117.92 (11) | C35—C36—H36 | 120.4 |
C16—C15—C28 | 120.84 (11) | C36—C37—C38 | 121.9 (2) |
C20—C15—C28 | 121.13 (11) | C36—C37—H37 | 125.3 (19) |
C15—C16—O8 | 122.23 (11) | C38—C37—H37 | 112.7 (19) |
C15—C16—C17 | 123.49 (11) | C37—C38—C39 | 118.8 (2) |
O8—C16—C17 | 114.28 (11) | C37—C38—H38 | 120.6 |
O7—C17—C18 | 123.99 (11) | C39—C38—H38 | 120.6 |
O7—C17—C16 | 116.41 (11) | C34—C39—C38 | 119.1 (2) |
C18—C17—C16 | 119.59 (11) | C34—C39—H39 | 114.5 (11) |
C17—C18—C27 | 116.73 (11) | C38—C39—H39 | 126.2 (11) |
C17—C18—C19 | 118.41 (11) | N2—C40—C41 | 109.12 (10) |
C27—C18—C19 | 124.85 (11) | N2—C40—H40B | 109.1 (10) |
C11—C19—C20 | 116.73 (10) | C41—C40—H40B | 110.6 (10) |
C11—C19—C18 | 123.47 (11) | N2—C40—H40A | 108.2 (10) |
C20—C19—C18 | 119.79 (10) | C41—C40—H40A | 110.7 (10) |
C14—C20—C19 | 118.94 (10) | H40B—C40—H40A | 109.0 (14) |
C14—C20—C15 | 120.42 (11) | C40—C41—C42 | 112.03 (11) |
C19—C20—C15 | 120.62 (11) | C40—C41—H41B | 108.1 (9) |
C3—C21—H21C | 110.2 (11) | C42—C41—H41B | 110.2 (9) |
C3—C21—H21B | 111.7 (11) | C40—C41—H41A | 108.6 (10) |
H21C—C21—H21B | 105.5 (15) | C42—C41—H41A | 109.4 (10) |
C3—C21—H21A | 111.5 (11) | H41B—C41—H41A | 108.5 (13) |
H21C—C21—H21A | 107.4 (15) | C43—C42—C41 | 114.88 (11) |
H21B—C21—H21A | 110.3 (15) | C43—C42—H42B | 108.8 (10) |
N1—C22—C8 | 124.29 (11) | C41—C42—H42B | 108.0 (10) |
N1—C22—H22A | 115.1 (9) | C43—C42—H42A | 109.5 (10) |
C8—C22—H22A | 120.6 (9) | C41—C42—H42A | 108.3 (10) |
C5—C23—C24 | 109.71 (13) | H42B—C42—H42A | 107.1 (14) |
C5—C23—C25 | 115.26 (12) | C48—C43—C44 | 118.12 (12) |
C24—C23—C25 | 110.91 (13) | C48—C43—C42 | 122.33 (12) |
C5—C23—H23 | 108.7 (10) | C44—C43—C42 | 119.53 (12) |
C24—C23—H23 | 105.8 (10) | C45—C44—C43 | 120.89 (14) |
C25—C23—H23 | 105.9 (10) | C45—C44—H44 | 118.8 (11) |
C23—C24—H24C | 111.3 (13) | C43—C44—H44 | 120.3 (11) |
C23—C24—H24B | 109.7 (13) | C46—C45—C44 | 120.23 (14) |
H24C—C24—H24B | 108.0 (19) | C46—C45—H45 | 119.9 (12) |
C23—C24—H24A | 109.8 (12) | C44—C45—H45 | 119.9 (12) |
H24C—C24—H24A | 108.8 (18) | C47—C46—C45 | 119.70 (13) |
H24B—C24—H24A | 109.2 (18) | C47—C46—H46 | 117.3 (11) |
C23—C25—H25C | 110.2 (12) | C45—C46—H46 | 123.0 (11) |
C23—C25—H25B | 112.3 (12) | C46—C47—C48 | 120.11 (14) |
H25C—C25—H25B | 105.7 (17) | C46—C47—H47 | 120.9 (11) |
C23—C25—H25A | 112.9 (12) | C48—C47—H47 | 119.0 (11) |
H25C—C25—H25A | 106.9 (17) | C47—C48—C43 | 120.93 (13) |
H25B—C25—H25A | 108.5 (17) | C47—C48—H48 | 118.8 (10) |
C13—C26—H26C | 111.6 (11) | C43—C48—H48 | 120.2 (10) |
O1—C1—C2—C3 | 176.20 (11) | O7—C17—C18—C27 | −0.14 (19) |
C9—C1—C2—C3 | −3.68 (18) | C16—C17—C18—C27 | −178.98 (11) |
O1—C1—C2—C12 | −4.88 (17) | O7—C17—C18—C19 | −179.37 (12) |
C9—C1—C2—C12 | 175.25 (11) | C16—C17—C18—C19 | 1.78 (18) |
C1—C2—C3—C4 | 0.86 (18) | O5—C11—C19—C20 | −178.19 (10) |
C12—C2—C3—C4 | −178.05 (11) | C12—C11—C19—C20 | 2.78 (18) |
C1—C2—C3—C21 | −178.83 (11) | O5—C11—C19—C18 | 2.61 (17) |
C12—C2—C3—C21 | 2.26 (18) | C12—C11—C19—C18 | −176.43 (11) |
C2—C3—C4—C10 | 1.27 (19) | C17—C18—C19—C11 | 177.14 (12) |
C21—C3—C4—C10 | −179.03 (12) | C27—C18—C19—C11 | −2.02 (19) |
C10—C5—C6—O4 | 175.05 (11) | C17—C18—C19—C20 | −2.04 (17) |
C23—C5—C6—O4 | −0.82 (19) | C27—C18—C19—C20 | 178.79 (11) |
C10—C5—C6—C7 | −3.38 (19) | C13—C14—C20—C19 | −0.61 (19) |
C23—C5—C6—C7 | −179.25 (12) | C13—C14—C20—C15 | 178.13 (12) |
C5—C6—C7—O3 | 179.74 (12) | C11—C19—C20—C14 | −1.44 (17) |
O4—C6—C7—O3 | 1.20 (16) | C18—C19—C20—C14 | 177.80 (11) |
C5—C6—C7—C8 | 0.82 (19) | C11—C19—C20—C15 | 179.82 (11) |
O4—C6—C7—C8 | −177.72 (11) | C18—C19—C20—C15 | −0.94 (17) |
O3—C7—C8—C22 | −1.10 (18) | C16—C15—C20—C14 | −174.48 (12) |
C6—C7—C8—C22 | 177.72 (11) | C28—C15—C20—C14 | 1.66 (19) |
O3—C7—C8—C9 | −177.83 (11) | C16—C15—C20—C19 | 4.24 (18) |
C6—C7—C8—C9 | 1.00 (17) | C28—C15—C20—C19 | −179.62 (12) |
O1—C1—C9—C10 | −175.73 (10) | C31—N1—C22—C8 | −174.68 (12) |
C2—C1—C9—C10 | 4.15 (17) | C7—C8—C22—N1 | −1.80 (18) |
O1—C1—C9—C8 | 5.88 (16) | C9—C8—C22—N1 | 174.71 (11) |
C2—C1—C9—C8 | −174.25 (11) | C6—C5—C23—C24 | 80.53 (16) |
C22—C8—C9—C1 | 1.79 (18) | C10—C5—C23—C24 | −95.23 (15) |
C7—C8—C9—C1 | 178.24 (11) | C6—C5—C23—C25 | −45.50 (18) |
C22—C8—C9—C10 | −176.56 (11) | C10—C5—C23—C25 | 138.75 (13) |
C7—C8—C9—C10 | −0.11 (16) | C40—N2—C27—C18 | −179.68 (12) |
C3—C4—C10—C9 | −0.71 (18) | C17—C18—C27—N2 | −0.41 (18) |
C3—C4—C10—C5 | 178.34 (12) | C19—C18—C27—N2 | 178.77 (12) |
C1—C9—C10—C4 | −1.89 (16) | C16—C15—C28—C30 | 82.86 (16) |
C8—C9—C10—C4 | 176.57 (10) | C20—C15—C28—C30 | −93.16 (14) |
C1—C9—C10—C5 | 179.06 (10) | C16—C15—C28—C29 | −41.98 (19) |
C8—C9—C10—C5 | −2.48 (17) | C20—C15—C28—C29 | 142.00 (13) |
C6—C5—C10—C4 | −174.83 (11) | C22—N1—C31—C32 | 78.61 (17) |
C23—C5—C10—C4 | 1.01 (18) | N1—C31—C32—C33 | 178.81 (14) |
C6—C5—C10—C9 | 4.20 (17) | C31—C32—C33—C34 | −59.9 (2) |
C23—C5—C10—C9 | −179.95 (11) | C32—C33—C34—C39 | 120.07 (19) |
O5—C11—C12—C13 | 179.00 (11) | C32—C33—C34—C35 | −59.0 (2) |
C19—C11—C12—C13 | −1.99 (18) | C39—C34—C35—C36 | 0.1 (3) |
O5—C11—C12—C2 | −2.52 (17) | C33—C34—C35—C36 | 179.16 (17) |
C19—C11—C12—C2 | 176.49 (11) | C34—C35—C36—C37 | 0.3 (3) |
C1—C2—C12—C11 | 88.34 (15) | C35—C36—C37—C38 | −0.6 (3) |
C3—C2—C12—C11 | −92.76 (14) | C36—C37—C38—C39 | 0.6 (4) |
C1—C2—C12—C13 | −93.21 (15) | C35—C34—C39—C38 | −0.1 (3) |
C3—C2—C12—C13 | 85.69 (15) | C33—C34—C39—C38 | −179.14 (17) |
C11—C12—C13—C14 | −0.18 (18) | C37—C38—C39—C34 | −0.2 (3) |
C2—C12—C13—C14 | −178.64 (11) | C27—N2—C40—C41 | −175.11 (12) |
C11—C12—C13—C26 | 179.73 (12) | N2—C40—C41—C42 | −177.77 (11) |
C2—C12—C13—C26 | 1.28 (19) | C40—C41—C42—C43 | 179.66 (11) |
C12—C13—C14—C20 | 1.5 (2) | C41—C42—C43—C48 | −6.83 (19) |
C26—C13—C14—C20 | −178.45 (13) | C41—C42—C43—C44 | 174.53 (12) |
C20—C15—C16—O8 | 175.44 (12) | C48—C43—C44—C45 | −1.1 (2) |
C28—C15—C16—O8 | −0.7 (2) | C42—C43—C44—C45 | 177.59 (13) |
C20—C15—C16—C17 | −4.6 (2) | C43—C44—C45—C46 | 0.4 (2) |
C28—C15—C16—C17 | 179.20 (12) | C44—C45—C46—C47 | 0.4 (2) |
C15—C16—C17—O7 | −177.25 (13) | C45—C46—C47—C48 | −0.4 (2) |
O8—C16—C17—O7 | 2.67 (18) | C46—C47—C48—C43 | −0.3 (2) |
C15—C16—C17—C18 | 1.7 (2) | C44—C43—C48—C47 | 1.1 (2) |
O8—C16—C17—C18 | −178.40 (12) | C42—C43—C48—C47 | −177.60 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H101···O7i | 0.85 (2) | 1.95 (2) | 2.591 (1) | 132 (2) |
N1—H111···O3 | 0.93 (2) | 1.77 (2) | 2.535 (1) | 137 (2) |
O4—H104···O5ii | 0.85 (2) | 2.48 (2) | 3.217 (1) | 146 (2) |
O4—H104···O3 | 0.85 (2) | 2.00 (2) | 2.578 (1) | 125 (2) |
O5—H105···O3ii | 0.86 (2) | 1.97 (2) | 2.640 (1) | 134 (2) |
N2—H112···O7 | 0.91 (2) | 1.77 (2) | 2.517 (1) | 138 (2) |
O8—H108···O7 | 0.87 (2) | 2.00 (2) | 2.585 (1) | 123 (2) |
O8—H108···O1iii | 0.87 (2) | 2.18 (2) | 2.982 (1) | 152 (2) |
Symmetry codes: (i) x, −y+1/2, z−1/2; (ii) −x, −y, −z+1; (iii) x, −y+1/2, z+1/2. |
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