Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024251/bi2023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024251/bi2023Isup2.hkl |
CCDC reference: 613583
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997) and DIRDIF99 (Beurskens et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CrystalStructure (Rigaku/MSC, 2005); software used to prepare material for publication: CrystalStructure.
C26H29N3O8 | F(000) = 1080 |
Mr = 511.52 | Dx = 1.294 Mg m−3 |
Monoclinic, P21 | Melting point: 456 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71070 Å |
a = 12.5459 (13) Å | Cell parameters from 4884 reflections |
b = 14.5417 (14) Å | θ = 1.4–27.9° |
c = 14.6939 (15) Å | µ = 0.10 mm−1 |
β = 101.563 (4)° | T = 294 K |
V = 2626.3 (5) Å3 | Block, colourless |
Z = 4 | 0.24 × 0.20 × 0.14 mm |
Rigaku Saturn CCD area-detector diffractometer | 5372 independent reflections |
Radiation source: rotating anode | 3777 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.043 |
ω scans | θmax = 26.0°, θmin = 1.4° |
Absorption correction: multi-scan Jacobson (1998) | h = −15→15 |
Tmin = 0.977, Tmax = 0.987 | k = −17→17 |
21856 measured reflections | l = −18→15 |
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)] = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.191 | w = 1/[σ2(Fo2) + (0.1155P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max < 0.001 |
5372 reflections | Δρmax = 0.41 e Å−3 |
685 parameters | Δρmin = −0.19 e Å−3 |
13 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.019 (3) |
Experimental. Spectroscopic analysis: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 1.28 (s, 3H), 1.34 (s, 3H), 1.38 (s, 3H), 1.44 (s, 3H), 3.61–3.71 (m, 2H), 3.85 (dd, J = 12.6 and 4.5 Hz, 1H), 3.96 (t, J = 6.6 Hz, 1H), 4.35 (t, J = 6.6 Hz, 1H), 4.74 (brs, 2H), 4.82 (d, J = 6.0 Hz, 1H), 7.16 (d, J = 7.5 Hz, 1H), 7.35 (t, J = 7.8 Hz, 1H), 7.63 (t, J = 8.1 Hz, 1H), 7.72 (s, 1H), 7.82 (d, J = 7.8 Hz, 1 H), 8.25 (d, J = 7.2 Hz, 1H), 8.33 (d, J = 6.9 Hz, 1H), 8.72 (s, 1H), 9.50 (brt, J = 14.4 Hz, 1H); 13C NMR (75 MHz, CDCl3, δ, p.p.m.): 171.53, 163.90, 148.07, 138.25, 136.41, 136.11, 133.69, 129.75, 129.20, 126.27, 123.05, 122.68, 122.54, 119.59, 111.62, 109.15, 82.40, 79.87, 77.56, 66.12, 62.62, 57.46, 26.88, 26.21, 25.20, 24.70. MS (ESI): 510.0 (C26H29N3O8 - H). Spectroscopic analysis: 1H NMR (300 MHz, CDCl3, δ, p.p.m.): 1.28 (s, 3H), 1.34 (s, 3H), 1.38 (s, 3H), 1.44 (s, 3H), 3.61–3.71 (m, 2H), 3.85 (dd, J = 12.6 and 4.5 Hz, 1H), 3.96 (t, J = 6.6 Hz, 1H), 4.35 (t, J = 6.6 Hz, 1H), 4.74 (brs, 2H), 4.82 (d, J = 6.0 Hz, 1H), 7.16 (d, J = 7.5 Hz, 1H), 7.35 (t, J = 7.8 Hz, 1H), 7.63 (t, J = 8.1 Hz, 1H), 7.72 (s, 1H), 7.82 (d, J = 7.8 Hz, 1 H), 8.25 (d, J = 7.2 Hz, 1H), 8.33 (d, J = 6.9 Hz, 1H), 8.72 (s, 1H), 9.50 (brt, J = 14.4 Hz, 1H); 13C NMR (75 MHz, CDCl3, δ, p.p.m.): 171.53, 163.90, 148.07, 138.25, 136.41, 136.11, 133.69, 129.75, 129.20, 126.27, 123.05, 122.68, 122.54, 119.59, 111.62, 109.15, 82.40, 79.87, 77.56, 66.12, 62.62, 57.46, 26.88, 26.21, 25.20, 24.70. MS (ESI): 510.0 (C26H29N3O8 - H). |
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 | ||
N1 | 0.1688 (3) | 0.7889 (3) | 0.7172 (3) | 0.0562 (10) | |
N3 | 0.9918 (4) | 0.7984 (4) | 0.9775 (4) | 0.0868 (16) | |
N4 | 0.3172 (3) | 0.7893 (3) | 0.3031 (3) | 0.0531 (10) | |
N6 | −0.4977 (4) | 0.7971 (4) | 0.0371 (4) | 0.0788 (14) | |
O1 | −0.0509 (3) | 0.7920 (4) | 0.5776 (3) | 0.0931 (14) | |
O2 | 0.0897 (3) | 0.8057 (3) | 0.5068 (3) | 0.0809 (12) | |
O3 | 0.2274 (3) | 0.5940 (3) | 0.6905 (3) | 0.0695 (11) | |
O4 | 0.3993 (3) | 0.5826 (3) | 0.7797 (3) | 0.0818 (12) | |
O5 | 0.1401 (3) | 0.8974 (3) | 0.8197 (3) | 0.0726 (11) | |
N2 | 0.5678 (3) | 0.9961 (3) | 0.8208 (3) | 0.0568 (11) | |
O7 | 0.5913 (3) | 0.8445 (3) | 0.8543 (3) | 0.0810 (13) | |
O8 | 0.9579 (5) | 0.7275 (4) | 0.9408 (5) | 0.137 (3) | |
O9 | 1.0825 (3) | 0.8066 (4) | 1.0249 (4) | 0.1078 (17) | |
O10 | 0.4061 (3) | 0.7838 (3) | 0.5163 (3) | 0.0785 (11) | |
O11 | 0.5349 (3) | 0.8105 (4) | 0.4347 (3) | 0.0804 (12) | |
O12 | 0.3022 (4) | 0.9939 (3) | 0.2901 (3) | 0.0850 (13) | |
O13 | 0.2135 (4) | 0.9952 (4) | 0.1398 (4) | 0.1029 (16) | |
O14 | 0.3627 (3) | 0.6897 (2) | 0.2004 (3) | 0.0690 (10) | |
N5 | −0.0746 (3) | 0.5947 (3) | 0.1851 (3) | 0.0588 (11) | |
O16 | −0.0932 (3) | 0.7493 (3) | 0.1639 (4) | 0.0844 (14) | |
O17 | −0.4650 (4) | 0.8691 (3) | 0.0751 (5) | 0.129 (2) | |
O18 | −0.5884 (3) | 0.7898 (3) | −0.0102 (3) | 0.0906 (14) | |
C1 | 0.0661 (4) | 0.7395 (4) | 0.7197 (4) | 0.0624 (14) | |
H1A | 0.0165 | 0.7774 | 0.7464 | 0.075* | |
H1B | 0.0796 | 0.6826 | 0.7546 | 0.075* | |
C2 | 0.0220 (5) | 0.7212 (4) | 0.6167 (4) | 0.0727 (16) | |
H2 | −0.0125 | 0.6606 | 0.6070 | 0.087* | |
C3 | 0.1198 (5) | 0.7289 (4) | 0.5669 (4) | 0.0654 (14) | |
H3 | 0.1309 | 0.6728 | 0.5332 | 0.078* | |
C4 | 0.2179 (4) | 0.7534 (4) | 0.6417 (4) | 0.0616 (13) | |
H4 | 0.2595 | 0.8024 | 0.6190 | 0.074* | |
C5 | 0.2917 (4) | 0.6691 (4) | 0.6695 (4) | 0.0653 (14) | |
H5 | 0.3255 | 0.6520 | 0.6173 | 0.078* | |
C6 | 0.2958 (4) | 0.5365 (4) | 0.7575 (4) | 0.0688 (15) | |
C7 | 0.3782 (5) | 0.6764 (4) | 0.7557 (5) | 0.0786 (18) | |
H7A | 0.4426 | 0.7069 | 0.7434 | 0.094* | |
H7B | 0.3521 | 0.7092 | 0.8043 | 0.094* | |
C8 | −0.0254 (5) | 0.8150 (6) | 0.4900 (5) | 0.0842 (19) | |
C9 | −0.0811 (7) | 0.7518 (7) | 0.4130 (6) | 0.124 (3) | |
H9A | −0.0639 | 0.6890 | 0.4304 | 0.187* | |
H9B | −0.0562 | 0.7656 | 0.3569 | 0.187* | |
H9C | −0.1584 | 0.7606 | 0.4030 | 0.187* | |
C10 | −0.0513 (7) | 0.9155 (6) | 0.4703 (6) | 0.113 (3) | |
H10A | −0.1274 | 0.9259 | 0.4680 | 0.170* | |
H10B | −0.0339 | 0.9319 | 0.4117 | 0.170* | |
H10C | −0.0091 | 0.9524 | 0.5186 | 0.170* | |
C11 | 0.2468 (6) | 0.5280 (7) | 0.8419 (5) | 0.113 (3) | |
H11A | 0.2395 | 0.5879 | 0.8672 | 0.170* | |
H11B | 0.2931 | 0.4907 | 0.8874 | 0.170* | |
H11C | 0.1764 | 0.4997 | 0.8252 | 0.170* | |
C12 | 0.3144 (5) | 0.4459 (4) | 0.7153 (5) | 0.090 (2) | |
H12A | 0.2471 | 0.4126 | 0.7007 | 0.135* | |
H12B | 0.3665 | 0.4110 | 0.7586 | 0.135* | |
H12C | 0.3417 | 0.4558 | 0.6596 | 0.135* | |
C13 | 0.1920 (4) | 0.8694 (3) | 0.7618 (4) | 0.0521 (12) | |
C14 | 0.2782 (4) | 0.9306 (3) | 0.7359 (4) | 0.0544 (12) | |
C15 | 0.3841 (4) | 0.9283 (3) | 0.7874 (4) | 0.0578 (13) | |
H15 | 0.4046 | 0.8835 | 0.8327 | 0.069* | |
C16 | 0.4593 (3) | 0.9935 (3) | 0.7707 (4) | 0.0532 (12) | |
C17 | 0.4260 (4) | 1.0619 (4) | 0.7051 (4) | 0.0655 (15) | |
H17 | 0.4747 | 1.1077 | 0.6961 | 0.079* | |
C18 | 0.3206 (5) | 1.0624 (4) | 0.6528 (5) | 0.0810 (19) | |
H18 | 0.3001 | 1.1060 | 0.6062 | 0.097* | |
C19 | 0.2471 (4) | 0.9986 (4) | 0.6700 (5) | 0.0728 (17) | |
H19 | 0.1756 | 1.0009 | 0.6373 | 0.087* | |
C20 | 0.6275 (4) | 0.9232 (3) | 0.8590 (4) | 0.0566 (13) | |
C21 | 0.7427 (4) | 0.9403 (3) | 0.9049 (4) | 0.0528 (12) | |
C22 | 0.8122 (4) | 0.8662 (4) | 0.9209 (4) | 0.0655 (15) | |
H22 | 0.7865 | 0.8076 | 0.9031 | 0.079* | |
C23 | 0.9198 (4) | 0.8784 (4) | 0.9634 (4) | 0.0626 (14) | |
C24 | 0.9624 (4) | 0.9644 (4) | 0.9904 (4) | 0.0641 (14) | |
H24 | 1.0355 | 0.9718 | 1.0177 | 0.077* | |
C25 | 0.8931 (4) | 1.0379 (4) | 0.9756 (4) | 0.0668 (15) | |
H25 | 0.9190 | 1.0961 | 0.9948 | 0.080* | |
C26 | 0.7850 (4) | 1.0272 (4) | 0.9324 (4) | 0.0616 (14) | |
H26 | 0.7399 | 1.0785 | 0.9216 | 0.074* | |
C27 | 0.2670 (4) | 0.8126 (4) | 0.3819 (4) | 0.0647 (14) | |
H27A | 0.2376 | 0.7582 | 0.4062 | 0.078* | |
H27B | 0.2091 | 0.8572 | 0.3640 | 0.078* | |
C28 | 0.3597 (4) | 0.8527 (4) | 0.4525 (4) | 0.0663 (14) | |
H28 | 0.3369 | 0.9066 | 0.4838 | 0.080* | |
C29 | 0.4510 (5) | 0.8764 (4) | 0.3990 (4) | 0.0642 (14) | |
H29 | 0.4760 | 0.9402 | 0.4082 | 0.077* | |
C30 | 0.4047 (4) | 0.8538 (3) | 0.2977 (3) | 0.0517 (11) | |
H30 | 0.4604 | 0.8228 | 0.2708 | 0.062* | |
C31 | 0.3642 (4) | 0.9384 (4) | 0.2399 (4) | 0.0616 (13) | |
H31 | 0.4265 | 0.9737 | 0.2282 | 0.074* | |
C32 | 0.2238 (6) | 1.0434 (5) | 0.2238 (5) | 0.092 (2) | |
C33 | 0.2857 (4) | 0.9213 (4) | 0.1491 (4) | 0.0702 (15) | |
H33A | 0.3238 | 0.9195 | 0.0979 | 0.084* | |
H33B | 0.2475 | 0.8635 | 0.1511 | 0.084* | |
C34 | 0.5203 (5) | 0.7815 (5) | 0.5233 (4) | 0.0741 (16) | |
C35 | 0.5783 (7) | 0.8443 (6) | 0.5982 (6) | 0.117 (3) | |
H35A | 0.5530 | 0.9062 | 0.5854 | 0.176* | |
H35B | 0.6552 | 0.8418 | 0.6000 | 0.176* | |
H35C | 0.5639 | 0.8252 | 0.6571 | 0.176* | |
C36 | 0.5587 (7) | 0.6837 (6) | 0.5377 (6) | 0.109 (3) | |
H36A | 0.5415 | 0.6604 | 0.5942 | 0.164* | |
H36B | 0.6360 | 0.6813 | 0.5417 | 0.164* | |
H36C | 0.5232 | 0.6467 | 0.4863 | 0.164* | |
C37 | 0.1139 (10) | 1.0354 (12) | 0.2478 (10) | 0.203 (6) | |
H37A | 0.0649 | 1.0779 | 0.2108 | 0.304* | |
H37B | 0.1192 | 1.0493 | 0.3124 | 0.304* | |
H37C | 0.0871 | 0.9739 | 0.2355 | 0.304* | |
C38 | 0.2699 (10) | 1.1340 (6) | 0.2016 (8) | 0.173 (4) | |
H38A | 0.3463 | 1.1273 | 0.2027 | 0.260* | |
H38B | 0.2592 | 1.1789 | 0.2468 | 0.260* | |
H38C | 0.2336 | 1.1538 | 0.1409 | 0.260* | |
C39 | 0.3061 (4) | 0.7098 (3) | 0.2586 (4) | 0.0506 (11) | |
C40 | 0.2182 (4) | 0.6449 (3) | 0.2734 (4) | 0.0544 (12) | |
C41 | 0.1122 (4) | 0.6578 (3) | 0.2287 (4) | 0.0536 (12) | |
H41 | 0.0922 | 0.7110 | 0.1944 | 0.064* | |
C42 | 0.0352 (4) | 0.5910 (3) | 0.2350 (4) | 0.0534 (12) | |
C43 | 0.0653 (4) | 0.5127 (4) | 0.2868 (5) | 0.0767 (18) | |
H43 | 0.0137 | 0.4678 | 0.2911 | 0.092* | |
C44 | 0.1716 (4) | 0.5010 (5) | 0.3323 (5) | 0.089 (2) | |
H44 | 0.1909 | 0.4488 | 0.3684 | 0.106* | |
C45 | 0.2491 (4) | 0.5652 (4) | 0.3249 (5) | 0.0763 (18) | |
H45 | 0.3213 | 0.5559 | 0.3538 | 0.092* | |
C46 | −0.1308 (4) | 0.6725 (4) | 0.1525 (4) | 0.0583 (13) | |
C47 | −0.2465 (4) | 0.6552 (3) | 0.1022 (4) | 0.0524 (12) | |
C48 | −0.3164 (4) | 0.7301 (3) | 0.0921 (4) | 0.0566 (13) | |
H48 | −0.2917 | 0.7875 | 0.1152 | 0.068* | |
C49 | −0.4235 (4) | 0.7179 (4) | 0.0469 (4) | 0.0578 (13) | |
C50 | −0.4628 (4) | 0.6361 (4) | 0.0106 (4) | 0.0645 (15) | |
H50 | −0.5351 | 0.6300 | −0.0194 | 0.077* | |
C51 | −0.3936 (5) | 0.5633 (4) | 0.0193 (5) | 0.0777 (18) | |
H51 | −0.4191 | 0.5069 | −0.0059 | 0.093* | |
C52 | −0.2858 (4) | 0.5712 (4) | 0.0649 (4) | 0.0628 (14) | |
H52 | −0.2401 | 0.5203 | 0.0704 | 0.075* | |
H5A | −0.111 (4) | 0.525 (4) | 0.177 (4) | 0.075 (17)* | |
H2A | 0.600 (4) | 1.048 (4) | 0.818 (4) | 0.061 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.050 (2) | 0.057 (2) | 0.064 (3) | −0.0079 (19) | 0.0164 (19) | −0.002 (2) |
N3 | 0.067 (3) | 0.075 (3) | 0.103 (4) | 0.017 (3) | −0.021 (3) | −0.004 (3) |
N4 | 0.046 (2) | 0.058 (2) | 0.056 (2) | −0.0083 (18) | 0.0116 (18) | −0.002 (2) |
N6 | 0.067 (3) | 0.071 (3) | 0.087 (4) | 0.014 (3) | −0.011 (3) | −0.006 (3) |
O1 | 0.060 (2) | 0.138 (4) | 0.078 (3) | 0.011 (3) | 0.007 (2) | 0.009 (3) |
O2 | 0.074 (2) | 0.097 (3) | 0.072 (3) | 0.011 (2) | 0.015 (2) | 0.018 (2) |
O3 | 0.061 (2) | 0.060 (2) | 0.079 (3) | −0.0043 (18) | −0.0052 (19) | 0.007 (2) |
O4 | 0.063 (2) | 0.070 (2) | 0.101 (3) | −0.0027 (19) | −0.009 (2) | −0.002 (2) |
O5 | 0.058 (2) | 0.067 (2) | 0.098 (3) | −0.0025 (19) | 0.028 (2) | −0.007 (2) |
N2 | 0.042 (2) | 0.046 (2) | 0.078 (3) | −0.0038 (19) | 0.002 (2) | 0.008 (2) |
O7 | 0.055 (2) | 0.053 (2) | 0.122 (4) | −0.0075 (17) | −0.015 (2) | 0.006 (2) |
O8 | 0.103 (4) | 0.081 (3) | 0.192 (6) | 0.034 (3) | −0.058 (4) | −0.027 (4) |
O9 | 0.056 (2) | 0.114 (4) | 0.133 (4) | 0.008 (3) | −0.029 (3) | 0.008 (3) |
O10 | 0.078 (3) | 0.086 (3) | 0.073 (3) | −0.001 (2) | 0.018 (2) | 0.010 (2) |
O11 | 0.062 (2) | 0.112 (3) | 0.065 (2) | 0.009 (2) | 0.0061 (18) | 0.021 (2) |
O12 | 0.112 (3) | 0.071 (2) | 0.069 (3) | 0.033 (2) | 0.010 (2) | 0.001 (2) |
O13 | 0.073 (3) | 0.104 (3) | 0.114 (4) | 0.024 (3) | −0.025 (3) | −0.012 (3) |
O14 | 0.061 (2) | 0.056 (2) | 0.095 (3) | 0.0001 (17) | 0.027 (2) | −0.012 (2) |
N5 | 0.039 (2) | 0.053 (2) | 0.082 (3) | −0.0001 (19) | 0.005 (2) | 0.007 (2) |
O16 | 0.057 (2) | 0.050 (2) | 0.130 (4) | −0.0052 (18) | −0.019 (2) | 0.007 (2) |
O17 | 0.096 (4) | 0.081 (3) | 0.177 (6) | 0.036 (3) | −0.049 (4) | −0.047 (4) |
O18 | 0.056 (2) | 0.106 (3) | 0.096 (3) | 0.022 (2) | −0.016 (2) | 0.002 (3) |
C1 | 0.054 (3) | 0.069 (3) | 0.064 (3) | −0.014 (3) | 0.011 (2) | 0.003 (3) |
C2 | 0.072 (4) | 0.073 (4) | 0.071 (4) | −0.017 (3) | 0.008 (3) | −0.003 (3) |
C3 | 0.070 (3) | 0.068 (3) | 0.057 (3) | 0.003 (3) | 0.007 (3) | 0.005 (3) |
C4 | 0.059 (3) | 0.063 (3) | 0.064 (3) | −0.006 (2) | 0.017 (2) | 0.005 (3) |
C5 | 0.057 (3) | 0.064 (3) | 0.076 (4) | −0.007 (2) | 0.017 (3) | 0.003 (3) |
C6 | 0.054 (3) | 0.071 (3) | 0.078 (4) | 0.003 (3) | 0.005 (3) | 0.005 (3) |
C7 | 0.062 (3) | 0.062 (3) | 0.104 (5) | −0.002 (3) | 0.001 (3) | 0.003 (3) |
C8 | 0.067 (4) | 0.114 (5) | 0.067 (4) | 0.008 (4) | 0.003 (3) | 0.007 (4) |
C9 | 0.136 (7) | 0.132 (7) | 0.087 (6) | −0.029 (6) | −0.022 (5) | 0.000 (5) |
C10 | 0.108 (6) | 0.126 (7) | 0.094 (5) | 0.040 (5) | −0.011 (4) | 0.006 (5) |
C11 | 0.095 (5) | 0.161 (8) | 0.088 (5) | 0.032 (5) | 0.027 (4) | 0.045 (5) |
C12 | 0.081 (4) | 0.070 (4) | 0.107 (5) | 0.014 (3) | −0.010 (4) | −0.004 (4) |
C13 | 0.039 (2) | 0.052 (3) | 0.064 (3) | 0.003 (2) | 0.005 (2) | 0.009 (2) |
C14 | 0.042 (2) | 0.049 (3) | 0.072 (3) | 0.002 (2) | 0.009 (2) | 0.008 (2) |
C15 | 0.044 (3) | 0.047 (3) | 0.077 (4) | −0.002 (2) | 0.000 (2) | 0.009 (2) |
C16 | 0.036 (2) | 0.050 (2) | 0.071 (3) | 0.000 (2) | 0.004 (2) | 0.012 (2) |
C17 | 0.048 (3) | 0.060 (3) | 0.086 (4) | −0.001 (2) | 0.008 (3) | 0.021 (3) |
C18 | 0.056 (3) | 0.082 (4) | 0.099 (5) | 0.005 (3) | 0.002 (3) | 0.045 (4) |
C19 | 0.042 (3) | 0.073 (3) | 0.096 (5) | −0.004 (3) | −0.005 (3) | 0.027 (3) |
C20 | 0.047 (3) | 0.046 (3) | 0.072 (3) | 0.000 (2) | 0.001 (2) | 0.001 (2) |
C21 | 0.051 (3) | 0.047 (2) | 0.057 (3) | 0.000 (2) | 0.002 (2) | 0.005 (2) |
C22 | 0.062 (3) | 0.061 (3) | 0.064 (4) | 0.002 (3) | −0.009 (3) | −0.003 (3) |
C23 | 0.051 (3) | 0.066 (3) | 0.064 (3) | 0.009 (2) | −0.005 (2) | 0.010 (3) |
C24 | 0.051 (3) | 0.069 (3) | 0.066 (4) | −0.012 (3) | −0.005 (3) | 0.002 (3) |
C25 | 0.058 (3) | 0.064 (3) | 0.071 (4) | −0.017 (3) | −0.004 (3) | 0.003 (3) |
C26 | 0.064 (3) | 0.055 (3) | 0.063 (3) | −0.002 (2) | 0.004 (3) | 0.004 (3) |
C27 | 0.058 (3) | 0.063 (3) | 0.077 (4) | 0.002 (3) | 0.024 (3) | −0.004 (3) |
C28 | 0.069 (3) | 0.064 (3) | 0.066 (4) | 0.004 (3) | 0.013 (3) | −0.004 (3) |
C29 | 0.064 (3) | 0.062 (3) | 0.063 (3) | −0.009 (3) | 0.004 (3) | 0.001 (3) |
C30 | 0.048 (2) | 0.049 (2) | 0.058 (3) | −0.010 (2) | 0.009 (2) | 0.006 (2) |
C31 | 0.055 (3) | 0.062 (3) | 0.066 (3) | −0.001 (2) | 0.008 (3) | 0.006 (3) |
C32 | 0.110 (5) | 0.075 (4) | 0.083 (5) | 0.031 (4) | 0.002 (4) | −0.002 (4) |
C33 | 0.068 (3) | 0.070 (3) | 0.070 (4) | 0.004 (3) | 0.009 (3) | 0.011 (3) |
C34 | 0.069 (4) | 0.089 (4) | 0.063 (4) | 0.002 (3) | 0.010 (3) | 0.002 (3) |
C35 | 0.116 (6) | 0.133 (7) | 0.089 (5) | −0.020 (6) | −0.013 (5) | −0.012 (5) |
C36 | 0.125 (6) | 0.110 (6) | 0.083 (5) | 0.030 (5) | −0.002 (5) | 0.013 (4) |
C37 | 0.171 (8) | 0.258 (10) | 0.192 (9) | 0.088 (8) | 0.064 (7) | 0.010 (8) |
C38 | 0.213 (9) | 0.083 (5) | 0.181 (8) | 0.001 (6) | −0.063 (7) | 0.012 (5) |
C39 | 0.040 (2) | 0.049 (3) | 0.062 (3) | −0.001 (2) | 0.008 (2) | 0.004 (2) |
C40 | 0.041 (2) | 0.058 (3) | 0.062 (3) | 0.002 (2) | 0.005 (2) | 0.002 (2) |
C41 | 0.046 (3) | 0.048 (2) | 0.065 (3) | 0.003 (2) | 0.006 (2) | 0.008 (2) |
C42 | 0.041 (2) | 0.049 (2) | 0.069 (3) | 0.003 (2) | 0.008 (2) | 0.007 (2) |
C43 | 0.050 (3) | 0.062 (3) | 0.113 (5) | −0.005 (2) | 0.003 (3) | 0.035 (3) |
C44 | 0.051 (3) | 0.077 (4) | 0.129 (6) | 0.000 (3) | −0.004 (3) | 0.047 (4) |
C45 | 0.039 (3) | 0.083 (4) | 0.103 (5) | −0.003 (3) | 0.006 (3) | 0.034 (3) |
C46 | 0.048 (3) | 0.052 (3) | 0.068 (3) | −0.001 (2) | −0.004 (2) | 0.007 (2) |
C47 | 0.044 (3) | 0.058 (3) | 0.053 (3) | −0.006 (2) | 0.004 (2) | 0.001 (2) |
C48 | 0.048 (3) | 0.045 (2) | 0.069 (3) | 0.004 (2) | −0.006 (2) | 0.000 (2) |
C49 | 0.049 (3) | 0.061 (3) | 0.058 (3) | 0.006 (2) | −0.005 (2) | 0.000 (2) |
C50 | 0.047 (3) | 0.066 (3) | 0.073 (4) | −0.003 (2) | −0.006 (3) | −0.009 (3) |
C51 | 0.072 (4) | 0.063 (3) | 0.089 (5) | −0.006 (3) | −0.005 (3) | −0.020 (3) |
C52 | 0.050 (3) | 0.061 (3) | 0.072 (4) | 0.007 (2) | −0.002 (3) | −0.009 (3) |
N1—C13 | 1.345 (7) | C15—C16 | 1.394 (7) |
N1—C4 | 1.466 (7) | C15—H15 | 0.930 |
N1—C1 | 1.482 (6) | C16—C17 | 1.389 (7) |
N3—O8 | 1.201 (7) | C17—C18 | 1.391 (8) |
N3—O9 | 1.215 (6) | C17—H17 | 0.930 |
N3—C23 | 1.462 (8) | C18—C19 | 1.367 (8) |
N4—C39 | 1.321 (6) | C18—H18 | 0.930 |
N4—C30 | 1.458 (6) | C19—H19 | 0.930 |
N4—C27 | 1.464 (7) | C20—C21 | 1.489 (7) |
N6—O18 | 1.213 (6) | C21—C22 | 1.376 (7) |
N6—O17 | 1.219 (7) | C21—C26 | 1.398 (7) |
N6—C49 | 1.470 (7) | C22—C23 | 1.381 (8) |
O1—C2 | 1.419 (8) | C22—H22 | 0.930 |
O1—C8 | 1.428 (8) | C23—C24 | 1.386 (8) |
O2—C8 | 1.422 (7) | C24—C25 | 1.368 (8) |
O2—C3 | 1.427 (7) | C24—H24 | 0.930 |
O3—C5 | 1.428 (6) | C25—C26 | 1.386 (7) |
O3—C6 | 1.437 (7) | C25—H25 | 0.930 |
O4—C7 | 1.420 (7) | C26—H26 | 0.930 |
O4—C6 | 1.440 (7) | C27—C28 | 1.512 (8) |
O5—C13 | 1.239 (6) | C27—H27A | 0.970 |
N2—C20 | 1.353 (6) | C27—H27B | 0.970 |
N2—C16 | 1.412 (6) | C28—C29 | 1.553 (8) |
N2—H2A | 0.87 (6) | C28—H28 | 0.980 |
O7—C20 | 1.228 (6) | C29—C30 | 1.520 (7) |
O10—C28 | 1.415 (7) | C29—H29 | 0.980 |
O10—C34 | 1.416 (7) | C30—C31 | 1.523 (7) |
O11—C34 | 1.415 (7) | C30—H30 | 0.980 |
O11—C29 | 1.443 (7) | C31—C33 | 1.511 (7) |
O12—C31 | 1.424 (7) | C31—H31 | 0.980 |
O12—C32 | 1.432 (8) | C32—C37 | 1.495 (14) |
O13—C33 | 1.394 (7) | C32—C38 | 1.501 (13) |
O13—C32 | 1.402 (9) | C33—H33A | 0.970 |
O14—C39 | 1.252 (6) | C33—H33B | 0.970 |
N5—C46 | 1.367 (7) | C34—C35 | 1.502 (10) |
N5—C42 | 1.426 (6) | C34—C36 | 1.503 (11) |
N5—H5A | 1.10 (6) | C35—H35A | 0.960 |
O16—C46 | 1.211 (6) | C35—H35B | 0.960 |
C1—C2 | 1.526 (8) | C35—H35C | 0.960 |
C1—H1A | 0.970 | C36—H36A | 0.960 |
C1—H1B | 0.970 | C36—H36B | 0.960 |
C2—C3 | 1.553 (8) | C36—H36C | 0.960 |
C2—H2 | 0.980 | C37—H37A | 0.960 |
C3—C4 | 1.518 (7) | C37—H37B | 0.960 |
C3—H3 | 0.980 | C37—H37C | 0.960 |
C4—C5 | 1.541 (8) | C38—H38A | 0.960 |
C4—H4 | 0.980 | C38—H38B | 0.960 |
C5—C7 | 1.497 (8) | C38—H38C | 0.960 |
C5—H5 | 0.980 | C39—C40 | 1.501 (7) |
C6—C12 | 1.495 (9) | C40—C41 | 1.373 (7) |
C6—C11 | 1.496 (9) | C40—C45 | 1.395 (7) |
C7—H7A | 0.970 | C41—C42 | 1.386 (7) |
C7—H7B | 0.970 | C41—H41 | 0.930 |
C8—C10 | 1.512 (11) | C42—C43 | 1.380 (7) |
C8—C9 | 1.515 (11) | C43—C44 | 1.377 (7) |
C9—H9A | 0.960 | C43—H43 | 0.930 |
C9—H9B | 0.960 | C44—C45 | 1.368 (8) |
C9—H9C | 0.960 | C44—H44 | 0.930 |
C10—H10A | 0.960 | C45—H45 | 0.930 |
C10—H10B | 0.960 | C46—C47 | 1.512 (7) |
C10—H10C | 0.960 | C47—C48 | 1.388 (7) |
C11—H11A | 0.960 | C47—C52 | 1.388 (7) |
C11—H11B | 0.960 | C48—C49 | 1.387 (7) |
C11—H11C | 0.960 | C48—H48 | 0.930 |
C12—H12A | 0.960 | C49—C50 | 1.354 (8) |
C12—H12B | 0.960 | C50—C51 | 1.359 (8) |
C12—H12C | 0.960 | C50—H50 | 0.930 |
C13—C14 | 1.507 (7) | C51—C52 | 1.388 (8) |
C14—C19 | 1.384 (7) | C51—H51 | 0.930 |
C14—C15 | 1.391 (7) | C52—H52 | 0.930 |
C13—N1—C4 | 126.4 (4) | C23—C22—H22 | 119.8 |
C13—N1—C1 | 120.9 (4) | C22—C23—C24 | 122.1 (5) |
C4—N1—C1 | 110.3 (4) | C22—C23—N3 | 118.9 (5) |
O8—N3—O9 | 123.2 (6) | C24—C23—N3 | 119.0 (5) |
O8—N3—C23 | 117.8 (5) | C25—C24—C23 | 117.6 (5) |
O9—N3—C23 | 118.9 (6) | C25—C24—H24 | 121.2 |
C39—N4—C30 | 122.8 (4) | C23—C24—H24 | 121.2 |
C39—N4—C27 | 125.1 (4) | C24—C25—C26 | 121.2 (5) |
C30—N4—C27 | 110.0 (4) | C24—C25—H25 | 119.4 |
O18—N6—O17 | 122.0 (5) | C26—C25—H25 | 119.4 |
O18—N6—C49 | 119.3 (5) | C25—C26—C21 | 120.9 (5) |
O17—N6—C49 | 118.7 (4) | C25—C26—H26 | 119.6 |
C2—O1—C8 | 107.0 (5) | C21—C26—H26 | 119.6 |
C8—O2—C3 | 108.4 (5) | N4—C27—C28 | 103.8 (4) |
C5—O3—C6 | 107.9 (4) | N4—C27—H27A | 111.0 |
C7—O4—C6 | 106.0 (4) | C28—C27—H27A | 111.0 |
C20—N2—C16 | 126.2 (5) | N4—C27—H27B | 111.0 |
C20—N2—H2A | 119 (4) | C28—C27—H27B | 111.0 |
C16—N2—H2A | 114 (4) | H27A—C27—H27B | 109.0 |
C28—O10—C34 | 110.0 (4) | O10—C28—C27 | 109.9 (5) |
C34—O11—C29 | 108.3 (4) | O10—C28—C29 | 104.2 (4) |
C31—O12—C32 | 107.7 (5) | C27—C28—C29 | 106.4 (5) |
C33—O13—C32 | 110.8 (5) | O10—C28—H28 | 112.0 |
C46—N5—C42 | 126.0 (4) | C27—C28—H28 | 112.0 |
C46—N5—H5A | 123 (3) | C29—C28—H28 | 112.0 |
C42—N5—H5A | 111 (3) | O11—C29—C30 | 108.7 (5) |
N1—C1—C2 | 101.7 (4) | O11—C29—C28 | 103.1 (4) |
N1—C1—H1A | 111.4 | C30—C29—C28 | 105.8 (4) |
C2—C1—H1A | 111.4 | O11—C29—H29 | 112.9 |
N1—C1—H1B | 111.4 | C30—C29—H29 | 112.9 |
C2—C1—H1B | 111.4 | C28—C29—H29 | 112.9 |
H1A—C1—H1B | 109.3 | N4—C30—C29 | 103.3 (4) |
O1—C2—C1 | 110.5 (5) | N4—C30—C31 | 112.3 (4) |
O1—C2—C3 | 105.2 (5) | C29—C30—C31 | 113.0 (4) |
C1—C2—C3 | 106.9 (4) | N4—C30—H30 | 109.4 |
O1—C2—H2 | 111.3 | C29—C30—H30 | 109.4 |
C1—C2—H2 | 111.3 | C31—C30—H30 | 109.4 |
C3—C2—H2 | 111.3 | O12—C31—C33 | 102.9 (4) |
O2—C3—C4 | 109.9 (5) | O12—C31—C30 | 108.9 (4) |
O2—C3—C2 | 102.3 (5) | C33—C31—C30 | 116.4 (4) |
C4—C3—C2 | 106.2 (5) | O12—C31—H31 | 109.4 |
O2—C3—H3 | 112.6 | C33—C31—H31 | 109.4 |
C4—C3—H3 | 112.6 | C30—C31—H31 | 109.4 |
C2—C3—H3 | 112.6 | O13—C32—O12 | 106.1 (5) |
N1—C4—C3 | 103.1 (4) | O13—C32—C37 | 104.0 (8) |
N1—C4—C5 | 113.6 (5) | O12—C32—C37 | 109.9 (8) |
C3—C4—C5 | 111.2 (5) | O13—C32—C38 | 102.7 (8) |
N1—C4—H4 | 109.5 | O12—C32—C38 | 110.4 (7) |
C3—C4—H4 | 109.5 | C37—C32—C38 | 122.2 (10) |
C5—C4—H4 | 109.5 | O13—C33—C31 | 104.8 (5) |
O3—C5—C7 | 102.5 (5) | O13—C33—H33A | 110.8 |
O3—C5—C4 | 109.2 (4) | C31—C33—H33A | 110.8 |
C7—C5—C4 | 117.6 (5) | O13—C33—H33B | 110.8 |
O3—C5—H5 | 109.1 | C31—C33—H33B | 110.8 |
C7—C5—H5 | 109.1 | H33A—C33—H33B | 108.9 |
C4—C5—H5 | 109.1 | O11—C34—O10 | 104.0 (4) |
O3—C6—O4 | 105.8 (4) | O11—C34—C35 | 111.1 (6) |
O3—C6—C12 | 110.5 (5) | O10—C34—C35 | 111.9 (6) |
O4—C6—C12 | 107.2 (5) | O11—C34—C36 | 108.3 (6) |
O3—C6—C11 | 109.2 (5) | O10—C34—C36 | 108.9 (6) |
O4—C6—C11 | 110.7 (6) | C35—C34—C36 | 112.2 (6) |
C12—C6—C11 | 113.2 (7) | C34—C35—H35A | 109.5 |
O4—C7—C5 | 102.1 (5) | C34—C35—H35B | 109.5 |
O4—C7—H7A | 111.3 | H35A—C35—H35B | 109.5 |
C5—C7—H7A | 111.3 | C34—C35—H35C | 109.5 |
O4—C7—H7B | 111.3 | H35A—C35—H35C | 109.5 |
C5—C7—H7B | 111.3 | H35B—C35—H35C | 109.5 |
H7A—C7—H7B | 109.2 | C34—C36—H36A | 109.5 |
O2—C8—O1 | 102.9 (4) | C34—C36—H36B | 109.5 |
O2—C8—C10 | 107.3 (6) | H36A—C36—H36B | 109.5 |
O1—C8—C10 | 108.7 (7) | C34—C36—H36C | 109.5 |
O2—C8—C9 | 111.8 (7) | H36A—C36—H36C | 109.5 |
O1—C8—C9 | 112.2 (7) | H36B—C36—H36C | 109.5 |
C10—C8—C9 | 113.2 (6) | C32—C37—H37A | 109.5 |
C8—C9—H9A | 109.5 | C32—C37—H37B | 109.5 |
C8—C9—H9B | 109.5 | H37A—C37—H37B | 109.5 |
H9A—C9—H9B | 109.5 | C32—C37—H37C | 109.5 |
C8—C9—H9C | 109.5 | H37A—C37—H37C | 109.5 |
H9A—C9—H9C | 109.5 | H37B—C37—H37C | 109.5 |
H9B—C9—H9C | 109.5 | C32—C38—H38A | 109.5 |
C8—C10—H10A | 109.5 | C32—C38—H38B | 109.5 |
C8—C10—H10B | 109.5 | H38A—C38—H38B | 109.5 |
H10A—C10—H10B | 109.5 | C32—C38—H38C | 109.5 |
C8—C10—H10C | 109.5 | H38A—C38—H38C | 109.5 |
H10A—C10—H10C | 109.5 | H38B—C38—H38C | 109.5 |
H10B—C10—H10C | 109.5 | O14—C39—N4 | 121.7 (4) |
C6—C11—H11A | 109.5 | O14—C39—C40 | 119.1 (5) |
C6—C11—H11B | 109.5 | N4—C39—C40 | 119.1 (4) |
H11A—C11—H11B | 109.5 | C41—C40—C45 | 120.7 (5) |
C6—C11—H11C | 109.5 | C41—C40—C39 | 120.9 (4) |
H11A—C11—H11C | 109.5 | C45—C40—C39 | 117.9 (4) |
H11B—C11—H11C | 109.5 | C40—C41—C42 | 119.5 (4) |
C6—C12—H12A | 109.5 | C40—C41—H41 | 120.2 |
C6—C12—H12B | 109.5 | C42—C41—H41 | 120.2 |
H12A—C12—H12B | 109.5 | C43—C42—C41 | 119.9 (4) |
C6—C12—H12C | 109.5 | C43—C42—N5 | 116.4 (5) |
H12A—C12—H12C | 109.5 | C41—C42—N5 | 123.6 (4) |
H12B—C12—H12C | 109.5 | C44—C43—C42 | 120.0 (5) |
O5—C13—N1 | 121.9 (5) | C44—C43—H43 | 120.0 |
O5—C13—C14 | 118.8 (5) | C42—C43—H43 | 120.0 |
N1—C13—C14 | 119.1 (5) | C45—C44—C43 | 120.8 (5) |
C19—C14—C15 | 120.2 (4) | C45—C44—H44 | 119.6 |
C19—C14—C13 | 118.8 (4) | C43—C44—H44 | 119.6 |
C15—C14—C13 | 120.3 (4) | C44—C45—C40 | 119.0 (5) |
C14—C15—C16 | 119.6 (4) | C44—C45—H45 | 120.5 |
C14—C15—H15 | 120.2 | C40—C45—H45 | 120.5 |
C16—C15—H15 | 120.2 | O16—C46—N5 | 123.8 (4) |
C17—C16—C15 | 119.3 (4) | O16—C46—C47 | 122.0 (4) |
C17—C16—N2 | 117.8 (4) | N5—C46—C47 | 114.2 (4) |
C15—C16—N2 | 122.8 (5) | C48—C47—C52 | 118.8 (4) |
C16—C17—C18 | 120.5 (5) | C48—C47—C46 | 116.4 (4) |
C16—C17—H17 | 119.8 | C52—C47—C46 | 124.8 (5) |
C18—C17—H17 | 119.8 | C49—C48—C47 | 118.8 (5) |
C19—C18—C17 | 119.7 (5) | C49—C48—H48 | 120.6 |
C19—C18—H18 | 120.1 | C47—C48—H48 | 120.6 |
C17—C18—H18 | 120.1 | C50—C49—C48 | 122.9 (5) |
C18—C19—C14 | 120.6 (5) | C50—C49—N6 | 118.4 (5) |
C18—C19—H19 | 119.7 | C48—C49—N6 | 118.7 (5) |
C14—C19—H19 | 119.7 | C49—C50—C51 | 118.1 (5) |
O7—C20—N2 | 122.7 (5) | C49—C50—H50 | 120.9 |
O7—C20—C21 | 119.7 (4) | C51—C50—H50 | 120.9 |
N2—C20—C21 | 117.6 (4) | C50—C51—C52 | 121.6 (5) |
C22—C21—C26 | 117.9 (4) | C50—C51—H51 | 119.2 |
C22—C21—C20 | 118.1 (4) | C52—C51—H51 | 119.2 |
C26—C21—C20 | 124.0 (4) | C51—C52—C47 | 119.8 (5) |
C21—C22—C23 | 120.4 (5) | C51—C52—H52 | 120.1 |
C21—C22—H22 | 119.8 | C47—C52—H52 | 120.1 |
C13—N1—C1—C2 | 129.2 (5) | C39—N4—C27—C28 | 131.9 (5) |
C4—N1—C1—C2 | −34.3 (6) | C30—N4—C27—C28 | −31.7 (5) |
C8—O1—C2—C1 | 136.4 (5) | C34—O10—C28—C27 | 128.7 (5) |
C8—O1—C2—C3 | 21.3 (6) | C34—O10—C28—C29 | 15.0 (6) |
N1—C1—C2—O1 | −93.7 (5) | N4—C27—C28—O10 | −95.9 (5) |
N1—C1—C2—C3 | 20.3 (6) | N4—C27—C28—C29 | 16.3 (6) |
C8—O2—C3—C4 | −136.2 (5) | C34—O11—C29—C30 | −135.4 (5) |
C8—O2—C3—C2 | −23.7 (6) | C34—O11—C29—C28 | −23.5 (6) |
O1—C2—C3—O2 | 1.3 (6) | O10—C28—C29—O11 | 5.1 (5) |
C1—C2—C3—O2 | −116.3 (5) | C27—C28—C29—O11 | −111.0 (5) |
O1—C2—C3—C4 | 116.4 (5) | O10—C28—C29—C30 | 119.2 (5) |
C1—C2—C3—C4 | −1.1 (6) | C27—C28—C29—C30 | 3.1 (6) |
C13—N1—C4—C3 | −128.4 (5) | C39—N4—C30—C29 | −130.4 (5) |
C1—N1—C4—C3 | 34.0 (5) | C27—N4—C30—C29 | 33.6 (5) |
C13—N1—C4—C5 | 111.1 (5) | C39—N4—C30—C31 | 107.5 (5) |
C1—N1—C4—C5 | −86.6 (5) | C27—N4—C30—C31 | −88.4 (5) |
O2—C3—C4—N1 | 91.1 (5) | O11—C29—C30—N4 | 88.9 (5) |
C2—C3—C4—N1 | −18.8 (6) | C28—C29—C30—N4 | −21.3 (5) |
O2—C3—C4—C5 | −146.8 (5) | O11—C29—C30—C31 | −149.6 (4) |
C2—C3—C4—C5 | 103.4 (5) | C28—C29—C30—C31 | 100.3 (5) |
C6—O3—C5—C7 | −25.8 (6) | C32—O12—C31—C33 | −27.7 (6) |
C6—O3—C5—C4 | −151.2 (4) | C32—O12—C31—C30 | −151.8 (5) |
N1—C4—C5—O3 | 64.9 (6) | N4—C30—C31—O12 | 71.2 (5) |
C3—C4—C5—O3 | −51.0 (6) | C29—C30—C31—O12 | −45.1 (6) |
N1—C4—C5—C7 | −51.3 (7) | N4—C30—C31—C33 | −44.5 (7) |
C3—C4—C5—C7 | −167.2 (5) | C29—C30—C31—C33 | −160.9 (5) |
C5—O3—C6—O4 | 3.6 (6) | C33—O13—C32—O12 | −3.3 (8) |
C5—O3—C6—C12 | −112.1 (5) | C33—O13—C32—C37 | −119.2 (8) |
C5—O3—C6—C11 | 122.8 (6) | C33—O13—C32—C38 | 112.5 (7) |
C7—O4—C6—O3 | 21.7 (6) | C31—O12—C32—O13 | 20.2 (7) |
C7—O4—C6—C12 | 139.6 (6) | C31—O12—C32—C37 | 132.1 (9) |
C7—O4—C6—C11 | −96.5 (7) | C31—O12—C32—C38 | −90.3 (8) |
C6—O4—C7—C5 | −37.1 (7) | C32—O13—C33—C31 | −13.6 (7) |
O3—C5—C7—O4 | 38.4 (6) | O12—C31—C33—O13 | 25.0 (6) |
C4—C5—C7—O4 | 158.2 (5) | C30—C31—C33—O13 | 144.1 (5) |
C3—O2—C8—O1 | 37.5 (7) | C29—O11—C34—O10 | 33.0 (6) |
C3—O2—C8—C10 | 152.1 (6) | C29—O11—C34—C35 | −87.5 (6) |
C3—O2—C8—C9 | −83.2 (7) | C29—O11—C34—C36 | 148.8 (6) |
C2—O1—C8—O2 | −35.9 (7) | C28—O10—C34—O11 | −29.8 (6) |
C2—O1—C8—C10 | −149.5 (6) | C28—O10—C34—C35 | 90.2 (6) |
C2—O1—C8—C9 | 84.4 (7) | C28—O10—C34—C36 | −145.2 (5) |
C4—N1—C13—O5 | 174.0 (5) | C30—N4—C39—O14 | −8.4 (7) |
C1—N1—C13—O5 | 13.3 (7) | C27—N4—C39—O14 | −170.0 (5) |
C4—N1—C13—C14 | −1.6 (7) | C30—N4—C39—C40 | 175.8 (4) |
C1—N1—C13—C14 | −162.3 (4) | C27—N4—C39—C40 | 14.2 (7) |
O5—C13—C14—C19 | −82.5 (7) | O14—C39—C40—C41 | −96.4 (6) |
N1—C13—C14—C19 | 93.3 (6) | N4—C39—C40—C41 | 79.5 (7) |
O5—C13—C14—C15 | 87.5 (6) | O14—C39—C40—C45 | 76.0 (7) |
N1—C13—C14—C15 | −96.7 (6) | N4—C39—C40—C45 | −108.1 (6) |
C19—C14—C15—C16 | −1.5 (9) | C45—C40—C41—C42 | 0.2 (8) |
C13—C14—C15—C16 | −171.4 (5) | C39—C40—C41—C42 | 172.4 (5) |
C14—C15—C16—C17 | 2.3 (8) | C40—C41—C42—C43 | 0.6 (8) |
C14—C15—C16—N2 | 179.3 (5) | C40—C41—C42—N5 | −174.7 (5) |
C20—N2—C16—C17 | −153.2 (6) | C46—N5—C42—C43 | 159.6 (6) |
C20—N2—C16—C15 | 29.8 (9) | C46—N5—C42—C41 | −24.9 (9) |
C15—C16—C17—C18 | −3.6 (9) | C41—C42—C43—C44 | 0.1 (10) |
N2—C16—C17—C18 | 179.3 (6) | N5—C42—C43—C44 | 175.8 (6) |
C16—C17—C18—C19 | 4.1 (10) | C42—C43—C44—C45 | −1.7 (12) |
C17—C18—C19—C14 | −3.3 (11) | C43—C44—C45—C40 | 2.5 (12) |
C15—C14—C19—C18 | 2.1 (10) | C41—C40—C45—C44 | −1.7 (10) |
C13—C14—C19—C18 | 172.1 (6) | C39—C40—C45—C44 | −174.1 (6) |
C16—N2—C20—O7 | −0.7 (9) | C42—N5—C46—O16 | −1.2 (9) |
C16—N2—C20—C21 | 176.8 (5) | C42—N5—C46—C47 | −179.8 (5) |
O7—C20—C21—C22 | 15.2 (8) | O16—C46—C47—C48 | −17.0 (8) |
N2—C20—C21—C22 | −162.4 (5) | N5—C46—C47—C48 | 161.6 (5) |
O7—C20—C21—C26 | −165.0 (6) | O16—C46—C47—C52 | 161.7 (6) |
N2—C20—C21—C26 | 17.3 (8) | N5—C46—C47—C52 | −19.6 (8) |
C26—C21—C22—C23 | 0.3 (8) | C52—C47—C48—C49 | 1.5 (8) |
C20—C21—C22—C23 | −180.0 (5) | C46—C47—C48—C49 | −179.7 (5) |
C21—C22—C23—C24 | −0.7 (10) | C47—C48—C49—C50 | −1.2 (9) |
C21—C22—C23—N3 | −178.7 (6) | C47—C48—C49—N6 | 179.3 (5) |
O8—N3—C23—C22 | 9.5 (10) | O18—N6—C49—C50 | −6.8 (9) |
O9—N3—C23—C22 | −170.8 (6) | O17—N6—C49—C50 | 175.0 (7) |
O8—N3—C23—C24 | −168.6 (8) | O18—N6—C49—C48 | 172.7 (6) |
O9—N3—C23—C24 | 11.1 (10) | O17—N6—C49—C48 | −5.5 (9) |
C22—C23—C24—C25 | 1.4 (9) | C48—C49—C50—C51 | 0.0 (10) |
N3—C23—C24—C25 | 179.5 (6) | N6—C49—C50—C51 | 179.5 (6) |
C23—C24—C25—C26 | −1.9 (9) | C49—C50—C51—C52 | 0.8 (11) |
C24—C25—C26—C21 | 1.7 (9) | C50—C51—C52—C47 | −0.5 (10) |
C22—C21—C26—C25 | −0.8 (8) | C48—C47—C52—C51 | −0.7 (9) |
C20—C21—C26—C25 | 179.5 (5) | C46—C47—C52—C51 | −179.4 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O14i | 0.87 (6) | 2.13 (6) | 2.981 (6) | 165 (5) |
N5—H5A···O5ii | 1.10 (6) | 1.90 (6) | 2.982 (6) | 166 (5) |
C24—H24···O13iii | 0.93 | 2.59 | 3.489 (7) | 162 |
C25—H25···O8iv | 0.93 | 2.52 | 3.418 (7) | 163 |
C51—H51···O17v | 0.93 | 2.56 | 3.473 (7) | 166 |
C52—H52···O5ii | 0.93 | 2.56 | 3.370 (7) | 146 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x, y−1/2, −z+1; (iii) x+1, y, z+1; (iv) −x+2, y+1/2, −z+2; (v) −x−1, y−1/2, −z. |