Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052949/cs2024sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052949/cs2024Isup2.hkl |
CCDC reference: 633663
Data collection: SMART and GEMINI (Siemens, 1995); cell refinement: SAINT (Siemens, 1995); data reduction: SAINT and XPREP (Siemens, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997), WinGX32 (Farrugia, 1999), POV-RAY (Cason, 2002) and WebLab ViewerPro (Molecular Simulations, 2000); software used to prepare material for publication: enCIFer (Version 1.0; Allen et al., 2004).
C20H20N2O4 | F(000) = 744 |
Mr = 352.38 | Dx = 1.401 Mg m−3 |
Monoclinic, Pc | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P -2yc | Cell parameters from 894 reflections |
a = 19.875 (9) Å | θ = 2.9–26.1° |
b = 7.393 (3) Å | µ = 0.10 mm−1 |
c = 11.529 (5) Å | T = 150 K |
β = 99.622 (9)° | Plate, colourless |
V = 1670.2 (13) Å3 | 0.50 × 0.17 × 0.11 mm |
Z = 4 |
Siemens SMART 1000 CCD area-detector diffractometer | 4288 independent reflections |
Radiation source: sealed tube | 3021 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
ω scans | θmax = 28.7°, θmin = 2.1° |
Absorption correction: multi-scan (TWINABS; Siemens, 1995) | h = 0→26 |
Tmin = 0.863, Tmax = 0.990 | k = −9→0 |
7366 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) = 0.095 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.0478P)2] where P = (Fo2 + 2Fc2)/3 |
4288 reflections | (Δ/σ)max < 0.001 |
474 parameters | Δρmax = 0.24 e Å−3 |
2 restraints | Δρmin = −0.24 e Å−3 |
Experimental. The crystal was coated in Exxon Paratone N hydrocarbon oil and mounted on a thin mohair fibre attached to a copper pin. Upon mounting on the diffractometer, the crystal was quenched to 150(K) under a cold nitrogen gas stream supplied by an Oxford Cryosystems Cryostream and data were collected at this temperature. 39 standard reflections were obtained by recollecting the first 50 CCD frames at the end of data collection. They were then used for a decay correction, giving an overall decay of 0.08%. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.8116 (3) | 0.3052 (8) | 0.8267 (5) | 0.0385 (15) | |
H1A | 0.8145 | 0.1854 | 0.7915 | 0.058* | |
H1B | 0.8557 | 0.3359 | 0.8744 | 0.058* | |
H1C | 0.8000 | 0.3954 | 0.7643 | 0.058* | |
C2 | 0.7576 (3) | 0.3035 (8) | 0.9033 (5) | 0.0268 (14) | |
H2A | 0.7705 | 0.2199 | 0.9704 | 0.032* | |
H2B | 0.7515 | 0.4261 | 0.9344 | 0.032* | |
C3 | 0.6412 (3) | 0.2359 (7) | 0.8846 (5) | 0.0226 (14) | |
C4 | 0.5779 (3) | 0.1769 (7) | 0.8054 (4) | 0.0195 (13) | |
C5 | 0.5161 (3) | 0.2081 (7) | 0.8400 (4) | 0.0185 (12) | |
H5 | 0.5145 | 0.2661 | 0.9131 | 0.022* | |
C6 | 0.4557 (3) | 0.1555 (6) | 0.7692 (5) | 0.0187 (12) | |
C7 | 0.4582 (3) | 0.0720 (7) | 0.6617 (4) | 0.0207 (13) | |
C8 | 0.5205 (3) | 0.0397 (7) | 0.6281 (4) | 0.0232 (14) | |
H8 | 0.5220 | −0.0191 | 0.5553 | 0.028* | |
C9 | 0.5812 (3) | 0.0912 (7) | 0.6982 (4) | 0.0232 (14) | |
H9 | 0.6239 | 0.0688 | 0.6741 | 0.028* | |
C10 | 0.3899 (3) | 0.1877 (7) | 0.8112 (4) | 0.0209 (13) | |
H10A | 0.3866 | 0.1066 | 0.8784 | 0.025* | |
H10B | 0.3882 | 0.3141 | 0.8387 | 0.025* | |
C11 | 0.3420 (3) | 0.0668 (7) | 0.6165 (4) | 0.0220 (13) | |
H11 | 0.3021 | 0.0346 | 0.5629 | 0.026* | |
C12 | 0.2664 (3) | 0.2071 (6) | 0.7335 (4) | 0.0197 (13) | |
C13 | 0.2540 (3) | 0.2440 (7) | 0.8448 (5) | 0.0227 (14) | |
H13 | 0.2898 | 0.2309 | 0.9100 | 0.027* | |
C14 | 0.1904 (3) | 0.2999 (7) | 0.8636 (4) | 0.0218 (13) | |
H14 | 0.1826 | 0.3245 | 0.9411 | 0.026* | |
C15 | 0.1379 (3) | 0.3199 (7) | 0.7685 (5) | 0.0226 (12) | |
C16 | 0.1507 (3) | 0.2877 (7) | 0.6589 (5) | 0.0305 (14) | |
H16 | 0.1150 | 0.3031 | 0.5938 | 0.037* | |
C17 | 0.2142 (3) | 0.2330 (7) | 0.6384 (5) | 0.0269 (14) | |
H17 | 0.2221 | 0.2134 | 0.5604 | 0.032* | |
C18 | 0.0700 (3) | 0.3787 (7) | 0.7931 (5) | 0.0294 (13) | |
C19 | −0.0460 (3) | 0.4234 (8) | 0.7090 (5) | 0.0408 (15) | |
H19A | −0.0459 | 0.4980 | 0.7804 | 0.049* | |
H19B | −0.0730 | 0.3126 | 0.7163 | 0.049* | |
C20 | −0.0767 (3) | 0.5275 (9) | 0.6016 (6) | 0.0561 (19) | |
H20A | −0.0532 | 0.6439 | 0.6004 | 0.084* | |
H20B | −0.1252 | 0.5487 | 0.6030 | 0.084* | |
H20C | −0.0717 | 0.4582 | 0.5311 | 0.084* | |
C21 | 0.1043 (3) | 0.8063 (8) | 0.6393 (5) | 0.0387 (16) | |
H21A | 0.1191 | 0.8862 | 0.5806 | 0.058* | |
H21B | 0.0620 | 0.8531 | 0.6612 | 0.058* | |
H21C | 0.0963 | 0.6846 | 0.6063 | 0.058* | |
C22 | 0.1587 (3) | 0.7986 (8) | 0.7464 (5) | 0.0314 (15) | |
H22A | 0.1655 | 0.9194 | 0.7836 | 0.038* | |
H22B | 0.1458 | 0.7123 | 0.8046 | 0.038* | |
C23 | 0.2764 (3) | 0.7289 (7) | 0.7903 (5) | 0.0260 (15) | |
C24 | 0.3367 (3) | 0.6715 (7) | 0.7437 (4) | 0.0205 (13) | |
C25 | 0.4002 (3) | 0.7046 (7) | 0.8112 (4) | 0.0203 (13) | |
H25 | 0.4029 | 0.7611 | 0.8859 | 0.024* | |
C26 | 0.4594 (3) | 0.6567 (6) | 0.7713 (5) | 0.0184 (12) | |
C27 | 0.4555 (3) | 0.5766 (6) | 0.6615 (5) | 0.0186 (12) | |
C28 | 0.3926 (3) | 0.5407 (7) | 0.5957 (4) | 0.0216 (13) | |
H28 | 0.3898 | 0.4814 | 0.5219 | 0.026* | |
C29 | 0.3340 (3) | 0.5895 (7) | 0.6353 (4) | 0.0205 (13) | |
H29 | 0.2910 | 0.5668 | 0.5878 | 0.025* | |
C30 | 0.5276 (3) | 0.6881 (7) | 0.8472 (4) | 0.0205 (14) | |
H30A | 0.5302 | 0.8146 | 0.8757 | 0.025* | |
H30B | 0.5323 | 0.6074 | 0.9166 | 0.025* | |
C31 | 0.5717 (3) | 0.5684 (7) | 0.6762 (4) | 0.0229 (14) | |
H31 | 0.6109 | 0.5370 | 0.6434 | 0.027* | |
C32 | 0.6498 (3) | 0.7126 (7) | 0.8322 (5) | 0.0212 (13) | |
C33 | 0.6643 (3) | 0.7538 (7) | 0.9523 (5) | 0.0253 (14) | |
H33 | 0.6298 | 0.7406 | 0.9997 | 0.030* | |
C34 | 0.7281 (3) | 0.8130 (7) | 1.0020 (5) | 0.0290 (14) | |
H34 | 0.7371 | 0.8423 | 1.0833 | 0.035* | |
C35 | 0.7792 (3) | 0.8306 (7) | 0.9357 (5) | 0.0279 (14) | |
C36 | 0.7659 (3) | 0.7901 (7) | 0.8172 (4) | 0.0246 (13) | |
H36 | 0.8010 | 0.8009 | 0.7708 | 0.030* | |
C37 | 0.7013 (3) | 0.7338 (7) | 0.7663 (5) | 0.0246 (14) | |
H37 | 0.6922 | 0.7092 | 0.6843 | 0.030* | |
C38 | 0.8470 (3) | 0.8982 (7) | 0.9930 (5) | 0.0306 (13) | |
C39 | 0.9601 (3) | 0.9588 (8) | 0.9650 (5) | 0.0378 (15) | |
H39A | 0.9807 | 0.8994 | 1.0394 | 0.045* | |
H39B | 0.9565 | 1.0902 | 0.9796 | 0.045* | |
C40 | 1.0028 (3) | 0.9256 (9) | 0.8715 (5) | 0.0513 (18) | |
H40A | 1.0075 | 0.7951 | 0.8604 | 0.077* | |
H40B | 1.0480 | 0.9795 | 0.8956 | 0.077* | |
H40C | 0.9808 | 0.9806 | 0.7975 | 0.077* | |
N1 | 0.3991 (3) | 0.0228 (5) | 0.5863 (3) | 0.0211 (11) | |
N2 | 0.3317 (2) | 0.1537 (6) | 0.7157 (4) | 0.0193 (10) | |
N3 | 0.5143 (3) | 0.5257 (6) | 0.6154 (4) | 0.0250 (12) | |
N4 | 0.5837 (2) | 0.6538 (6) | 0.7827 (4) | 0.0222 (11) | |
O1 | 0.6950 (2) | 0.2430 (5) | 0.8296 (3) | 0.0288 (10) | |
O2 | 0.6426 (2) | 0.2796 (6) | 0.9850 (3) | 0.0364 (11) | |
O3 | 0.0586 (2) | 0.4252 (6) | 0.8876 (3) | 0.0550 (13) | |
O4 | 0.0230 (2) | 0.3763 (6) | 0.6969 (3) | 0.0407 (11) | |
O5 | 0.2203 (2) | 0.7395 (5) | 0.7064 (3) | 0.0253 (10) | |
O6 | 0.2746 (2) | 0.7638 (6) | 0.8913 (3) | 0.0367 (12) | |
O7 | 0.8588 (2) | 0.9626 (5) | 1.0894 (3) | 0.0409 (10) | |
O8 | 0.89337 (19) | 0.8836 (5) | 0.9222 (3) | 0.0336 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.020 (3) | 0.049 (4) | 0.045 (4) | −0.009 (3) | 0.000 (3) | −0.002 (3) |
C2 | 0.020 (4) | 0.029 (3) | 0.029 (3) | −0.002 (3) | −0.003 (2) | −0.008 (2) |
C3 | 0.023 (4) | 0.022 (3) | 0.025 (3) | −0.002 (3) | 0.008 (3) | 0.001 (3) |
C4 | 0.028 (4) | 0.016 (3) | 0.012 (3) | 0.004 (2) | −0.002 (2) | 0.000 (2) |
C5 | 0.022 (3) | 0.016 (3) | 0.018 (3) | 0.007 (2) | 0.006 (2) | 0.003 (2) |
C6 | 0.023 (3) | 0.014 (3) | 0.018 (3) | −0.003 (3) | 0.001 (2) | 0.003 (2) |
C7 | 0.030 (4) | 0.016 (3) | 0.015 (3) | 0.002 (3) | 0.000 (3) | 0.000 (2) |
C8 | 0.038 (4) | 0.019 (3) | 0.013 (3) | 0.007 (3) | 0.007 (3) | 0.004 (2) |
C9 | 0.026 (4) | 0.025 (3) | 0.018 (3) | 0.004 (3) | 0.001 (3) | 0.006 (2) |
C10 | 0.021 (3) | 0.021 (3) | 0.018 (3) | −0.004 (3) | −0.002 (2) | −0.001 (2) |
C11 | 0.030 (4) | 0.017 (3) | 0.017 (3) | −0.002 (3) | −0.002 (3) | −0.001 (2) |
C12 | 0.025 (4) | 0.014 (3) | 0.018 (3) | 0.001 (2) | −0.002 (2) | −0.002 (2) |
C13 | 0.029 (4) | 0.021 (3) | 0.015 (3) | −0.004 (2) | −0.005 (3) | −0.001 (2) |
C14 | 0.026 (4) | 0.025 (3) | 0.015 (3) | 0.002 (2) | 0.004 (2) | −0.001 (2) |
C15 | 0.021 (3) | 0.025 (3) | 0.021 (3) | −0.002 (2) | 0.004 (2) | −0.001 (2) |
C16 | 0.023 (3) | 0.034 (3) | 0.031 (3) | −0.004 (3) | −0.006 (2) | 0.005 (3) |
C17 | 0.030 (4) | 0.030 (3) | 0.021 (3) | −0.002 (3) | 0.006 (3) | −0.002 (2) |
C18 | 0.027 (3) | 0.035 (3) | 0.025 (3) | −0.002 (2) | 0.002 (3) | 0.000 (3) |
C19 | 0.023 (3) | 0.059 (4) | 0.041 (3) | 0.003 (3) | 0.006 (3) | −0.005 (3) |
C20 | 0.042 (4) | 0.059 (4) | 0.068 (5) | 0.012 (3) | 0.009 (4) | 0.021 (4) |
C21 | 0.032 (4) | 0.046 (4) | 0.037 (4) | −0.001 (3) | 0.002 (3) | −0.010 (3) |
C22 | 0.024 (4) | 0.035 (3) | 0.034 (3) | 0.000 (3) | 0.005 (3) | −0.001 (3) |
C23 | 0.033 (4) | 0.023 (3) | 0.022 (3) | −0.008 (3) | 0.005 (3) | −0.001 (3) |
C24 | 0.017 (3) | 0.021 (3) | 0.021 (3) | −0.002 (2) | −0.003 (2) | 0.004 (2) |
C25 | 0.033 (4) | 0.018 (3) | 0.011 (2) | 0.003 (3) | 0.006 (2) | 0.002 (2) |
C26 | 0.026 (4) | 0.016 (3) | 0.013 (3) | −0.005 (3) | 0.000 (2) | 0.003 (2) |
C27 | 0.024 (4) | 0.014 (3) | 0.018 (3) | 0.003 (3) | 0.004 (3) | 0.007 (2) |
C28 | 0.029 (4) | 0.020 (3) | 0.016 (3) | 0.002 (3) | 0.005 (3) | 0.001 (2) |
C29 | 0.026 (4) | 0.020 (3) | 0.012 (3) | −0.002 (3) | −0.007 (2) | 0.005 (2) |
C30 | 0.031 (4) | 0.021 (3) | 0.009 (2) | −0.003 (3) | 0.001 (2) | −0.002 (2) |
C31 | 0.035 (4) | 0.022 (3) | 0.013 (3) | 0.005 (3) | 0.007 (3) | 0.000 (2) |
C32 | 0.019 (4) | 0.021 (3) | 0.020 (3) | 0.005 (3) | −0.009 (3) | 0.003 (2) |
C33 | 0.024 (4) | 0.030 (3) | 0.021 (3) | 0.004 (2) | 0.001 (3) | 0.001 (2) |
C34 | 0.032 (4) | 0.031 (3) | 0.022 (3) | 0.002 (3) | −0.004 (3) | −0.001 (2) |
C35 | 0.029 (4) | 0.028 (3) | 0.027 (3) | 0.004 (3) | 0.005 (3) | 0.003 (2) |
C36 | 0.029 (4) | 0.026 (3) | 0.018 (3) | 0.000 (3) | 0.003 (2) | 0.001 (2) |
C37 | 0.029 (4) | 0.027 (3) | 0.017 (3) | 0.002 (2) | 0.001 (3) | 0.002 (2) |
C38 | 0.033 (4) | 0.029 (3) | 0.029 (3) | 0.003 (3) | 0.002 (3) | 0.001 (2) |
C39 | 0.026 (3) | 0.041 (4) | 0.044 (3) | −0.010 (3) | 0.000 (3) | −0.005 (3) |
C40 | 0.035 (4) | 0.062 (4) | 0.059 (4) | −0.016 (3) | 0.014 (3) | −0.013 (4) |
N1 | 0.022 (3) | 0.024 (3) | 0.015 (2) | −0.005 (2) | −0.002 (2) | −0.001 (2) |
N2 | 0.017 (3) | 0.023 (3) | 0.017 (2) | −0.002 (2) | 0.000 (2) | −0.001 (2) |
N3 | 0.031 (4) | 0.024 (3) | 0.018 (2) | −0.006 (2) | −0.001 (2) | −0.004 (2) |
N4 | 0.024 (3) | 0.021 (2) | 0.021 (3) | −0.001 (2) | 0.003 (2) | 0.000 (2) |
O1 | 0.022 (3) | 0.036 (2) | 0.027 (2) | −0.0032 (18) | −0.0007 (19) | −0.0027 (18) |
O2 | 0.022 (3) | 0.068 (3) | 0.018 (2) | 0.003 (2) | −0.0009 (18) | −0.007 (2) |
O3 | 0.031 (3) | 0.103 (4) | 0.030 (2) | 0.025 (2) | 0.001 (2) | −0.009 (2) |
O4 | 0.019 (2) | 0.066 (3) | 0.036 (2) | 0.002 (2) | 0.0009 (19) | −0.004 (2) |
O5 | 0.019 (2) | 0.034 (2) | 0.023 (2) | 0.0006 (18) | 0.0016 (18) | −0.0038 (18) |
O6 | 0.032 (3) | 0.052 (3) | 0.026 (2) | 0.003 (2) | 0.006 (2) | −0.010 (2) |
O7 | 0.039 (3) | 0.052 (2) | 0.030 (2) | −0.005 (2) | 0.0012 (19) | −0.010 (2) |
O8 | 0.022 (2) | 0.047 (2) | 0.030 (2) | −0.0047 (19) | 0.0011 (17) | −0.0051 (18) |
C1—C2 | 1.500 (7) | C21—C22 | 1.500 (7) |
C1—H1A | 0.9800 | C21—H21A | 0.9800 |
C1—H1B | 0.9800 | C21—H21B | 0.9800 |
C1—H1C | 0.9800 | C21—H21C | 0.9800 |
C2—O1 | 1.455 (6) | C22—O5 | 1.446 (6) |
C2—H2A | 0.9900 | C22—H22A | 0.9900 |
C2—H2B | 0.9900 | C22—H22B | 0.9900 |
C3—O2 | 1.198 (6) | C23—O6 | 1.198 (6) |
C3—O1 | 1.331 (7) | C23—O5 | 1.350 (7) |
C3—C4 | 1.491 (8) | C23—C24 | 1.457 (8) |
C4—C5 | 1.374 (7) | C24—C29 | 1.382 (7) |
C4—C9 | 1.400 (7) | C24—C25 | 1.390 (8) |
C5—C6 | 1.389 (8) | C25—C26 | 1.379 (7) |
C5—H5 | 0.9500 | C25—H25 | 0.9500 |
C6—C7 | 1.393 (6) | C26—C27 | 1.388 (6) |
C6—C10 | 1.488 (8) | C26—C30 | 1.504 (8) |
C7—C8 | 1.379 (8) | C27—C28 | 1.376 (8) |
C7—N1 | 1.388 (7) | C27—N3 | 1.414 (7) |
C8—C9 | 1.388 (8) | C28—C29 | 1.368 (7) |
C8—H8 | 0.9500 | C28—H28 | 0.9500 |
C9—H9 | 0.9500 | C29—H29 | 0.9500 |
C10—N2 | 1.479 (7) | C30—N4 | 1.462 (7) |
C10—H10A | 0.9900 | C30—H30A | 0.9900 |
C10—H10B | 0.9900 | C30—H30B | 0.9900 |
C11—N1 | 1.283 (7) | C31—N3 | 1.274 (7) |
C11—N2 | 1.357 (6) | C31—N4 | 1.365 (6) |
C11—H11 | 0.9500 | C31—H31 | 0.9500 |
C12—C13 | 1.373 (7) | C32—C37 | 1.381 (8) |
C12—C17 | 1.390 (7) | C32—C33 | 1.400 (7) |
C12—N2 | 1.404 (7) | C32—N4 | 1.411 (7) |
C13—C14 | 1.382 (8) | C33—C34 | 1.374 (8) |
C13—H13 | 0.9500 | C33—H33 | 0.9500 |
C14—C15 | 1.389 (7) | C34—C35 | 1.375 (7) |
C14—H14 | 0.9500 | C34—H34 | 0.9500 |
C15—C16 | 1.352 (7) | C35—C36 | 1.380 (7) |
C15—C18 | 1.488 (7) | C35—C38 | 1.485 (8) |
C16—C17 | 1.383 (7) | C36—C37 | 1.383 (8) |
C16—H16 | 0.9500 | C36—H36 | 0.9500 |
C17—H17 | 0.9500 | C37—H37 | 0.9500 |
C18—O3 | 1.200 (6) | C38—O7 | 1.196 (6) |
C18—O4 | 1.325 (6) | C38—O8 | 1.333 (6) |
C19—O4 | 1.444 (7) | C39—O8 | 1.446 (6) |
C19—C20 | 1.499 (7) | C39—C40 | 1.499 (7) |
C19—H19A | 0.9900 | C39—H39A | 0.9900 |
C19—H19B | 0.9900 | C39—H39B | 0.9900 |
C20—H20A | 0.9800 | C40—H40A | 0.9800 |
C20—H20B | 0.9800 | C40—H40B | 0.9800 |
C20—H20C | 0.9800 | C40—H40C | 0.9800 |
C2—C1—H1A | 109.5 | O5—C22—C21 | 106.3 (5) |
C2—C1—H1B | 109.5 | O5—C22—H22A | 110.5 |
H1A—C1—H1B | 109.5 | C21—C22—H22A | 110.5 |
C2—C1—H1C | 109.5 | O5—C22—H22B | 110.5 |
H1A—C1—H1C | 109.5 | C21—C22—H22B | 110.5 |
H1B—C1—H1C | 109.5 | H22A—C22—H22B | 108.7 |
O1—C2—C1 | 106.6 (4) | O6—C23—O5 | 122.0 (6) |
O1—C2—H2A | 110.4 | O6—C23—C24 | 125.4 (6) |
C1—C2—H2A | 110.4 | O5—C23—C24 | 112.6 (5) |
O1—C2—H2B | 110.4 | C29—C24—C25 | 118.6 (5) |
C1—C2—H2B | 110.4 | C29—C24—C23 | 123.5 (5) |
H2A—C2—H2B | 108.6 | C25—C24—C23 | 117.9 (5) |
O2—C3—O1 | 124.0 (6) | C26—C25—C24 | 120.9 (5) |
O2—C3—C4 | 123.4 (6) | C26—C25—H25 | 119.5 |
O1—C3—C4 | 112.5 (5) | C24—C25—H25 | 119.5 |
C5—C4—C9 | 120.6 (5) | C25—C26—C27 | 119.5 (5) |
C5—C4—C3 | 118.5 (5) | C25—C26—C30 | 120.2 (5) |
C9—C4—C3 | 120.9 (5) | C27—C26—C30 | 120.3 (5) |
C4—C5—C6 | 120.6 (5) | C28—C27—C26 | 119.5 (5) |
C4—C5—H5 | 119.7 | C28—C27—N3 | 118.3 (5) |
C6—C5—H5 | 119.7 | C26—C27—N3 | 122.1 (5) |
C5—C6—C7 | 119.4 (6) | C29—C28—C27 | 120.7 (5) |
C5—C6—C10 | 118.9 (5) | C29—C28—H28 | 119.6 |
C7—C6—C10 | 121.6 (5) | C27—C28—H28 | 119.6 |
C8—C7—N1 | 119.0 (5) | C28—C29—C24 | 120.7 (5) |
C8—C7—C6 | 119.6 (6) | C28—C29—H29 | 119.6 |
N1—C7—C6 | 121.4 (6) | C24—C29—H29 | 119.6 |
C7—C8—C9 | 121.6 (5) | N4—C30—C26 | 111.6 (4) |
C7—C8—H8 | 119.2 | N4—C30—H30A | 109.3 |
C9—C8—H8 | 119.2 | C26—C30—H30A | 109.3 |
C8—C9—C4 | 118.2 (5) | N4—C30—H30B | 109.3 |
C8—C9—H9 | 120.9 | C26—C30—H30B | 109.3 |
C4—C9—H9 | 120.9 | H30A—C30—H30B | 108.0 |
N2—C10—C6 | 110.6 (4) | N3—C31—N4 | 128.0 (6) |
N2—C10—H10A | 109.5 | N3—C31—H31 | 116.0 |
C6—C10—H10A | 109.5 | N4—C31—H31 | 116.0 |
N2—C10—H10B | 109.5 | C37—C32—C33 | 118.1 (5) |
C6—C10—H10B | 109.5 | C37—C32—N4 | 122.6 (5) |
H10A—C10—H10B | 108.1 | C33—C32—N4 | 119.4 (5) |
N1—C11—N2 | 127.8 (5) | C34—C33—C32 | 120.3 (6) |
N1—C11—H11 | 116.1 | C34—C33—H33 | 119.9 |
N2—C11—H11 | 116.1 | C32—C33—H33 | 119.9 |
C13—C12—C17 | 118.9 (6) | C33—C34—C35 | 121.0 (5) |
C13—C12—N2 | 120.4 (5) | C33—C34—H34 | 119.5 |
C17—C12—N2 | 120.6 (5) | C35—C34—H34 | 119.5 |
C12—C13—C14 | 121.2 (5) | C34—C35—C36 | 119.5 (6) |
C12—C13—H13 | 119.4 | C34—C35—C38 | 118.9 (5) |
C14—C13—H13 | 119.4 | C36—C35—C38 | 121.5 (5) |
C13—C14—C15 | 119.6 (5) | C35—C36—C37 | 119.7 (5) |
C13—C14—H14 | 120.2 | C35—C36—H36 | 120.2 |
C15—C14—H14 | 120.2 | C37—C36—H36 | 120.2 |
C16—C15—C14 | 119.0 (6) | C32—C37—C36 | 121.4 (5) |
C16—C15—C18 | 123.2 (5) | C32—C37—H37 | 119.3 |
C14—C15—C18 | 117.8 (5) | C36—C37—H37 | 119.3 |
C15—C16—C17 | 122.1 (5) | O7—C38—O8 | 123.5 (6) |
C15—C16—H16 | 118.9 | O7—C38—C35 | 124.8 (6) |
C17—C16—H16 | 118.9 | O8—C38—C35 | 111.7 (5) |
C16—C17—C12 | 119.2 (5) | O8—C39—C40 | 106.8 (4) |
C16—C17—H17 | 120.4 | O8—C39—H39A | 110.4 |
C12—C17—H17 | 120.4 | C40—C39—H39A | 110.4 |
O3—C18—O4 | 123.3 (5) | O8—C39—H39B | 110.4 |
O3—C18—C15 | 124.8 (5) | C40—C39—H39B | 110.4 |
O4—C18—C15 | 111.8 (5) | H39A—C39—H39B | 108.6 |
O4—C19—C20 | 107.8 (5) | C39—C40—H40A | 109.5 |
O4—C19—H19A | 110.1 | C39—C40—H40B | 109.5 |
C20—C19—H19A | 110.1 | H40A—C40—H40B | 109.5 |
O4—C19—H19B | 110.1 | C39—C40—H40C | 109.5 |
C20—C19—H19B | 110.1 | H40A—C40—H40C | 109.5 |
H19A—C19—H19B | 108.5 | H40B—C40—H40C | 109.5 |
C19—C20—H20A | 109.5 | C11—N1—C7 | 117.3 (4) |
C19—C20—H20B | 109.5 | C11—N2—C12 | 122.0 (5) |
H20A—C20—H20B | 109.5 | C11—N2—C10 | 119.9 (5) |
C19—C20—H20C | 109.5 | C12—N2—C10 | 118.1 (4) |
H20A—C20—H20C | 109.5 | C31—N3—C27 | 116.6 (5) |
H20B—C20—H20C | 109.5 | C31—N4—C32 | 121.2 (5) |
C22—C21—H21A | 109.5 | C31—N4—C30 | 120.2 (5) |
C22—C21—H21B | 109.5 | C32—N4—C30 | 118.6 (4) |
H21A—C21—H21B | 109.5 | C3—O1—C2 | 114.2 (4) |
C22—C21—H21C | 109.5 | C18—O4—C19 | 117.7 (4) |
H21A—C21—H21C | 109.5 | C23—O5—C22 | 115.5 (4) |
H21B—C21—H21C | 109.5 | C38—O8—C39 | 116.7 (4) |
O2—C3—C4—C5 | 13.6 (8) | C25—C26—C30—N4 | −171.4 (4) |
O1—C3—C4—C5 | −163.2 (4) | C27—C26—C30—N4 | 9.6 (6) |
O2—C3—C4—C9 | −166.2 (5) | C37—C32—C33—C34 | −0.1 (8) |
O1—C3—C4—C9 | 17.0 (7) | N4—C32—C33—C34 | −179.3 (5) |
C9—C4—C5—C6 | −0.2 (8) | C32—C33—C34—C35 | −1.0 (9) |
C3—C4—C5—C6 | 180.0 (5) | C33—C34—C35—C36 | 0.8 (8) |
C4—C5—C6—C7 | −0.6 (7) | C33—C34—C35—C38 | 179.0 (5) |
C4—C5—C6—C10 | 178.5 (4) | C34—C35—C36—C37 | 0.5 (8) |
C5—C6—C7—C8 | 1.2 (7) | C38—C35—C36—C37 | −177.6 (5) |
C10—C6—C7—C8 | −177.9 (5) | C33—C32—C37—C36 | 1.4 (8) |
C5—C6—C7—N1 | −177.8 (5) | N4—C32—C37—C36 | −179.4 (5) |
C10—C6—C7—N1 | 3.2 (7) | C35—C36—C37—C32 | −1.6 (8) |
N1—C7—C8—C9 | 177.9 (5) | C34—C35—C38—O7 | −10.7 (8) |
C6—C7—C8—C9 | −1.0 (7) | C36—C35—C38—O7 | 167.5 (5) |
C7—C8—C9—C4 | 0.3 (7) | C34—C35—C38—O8 | 171.2 (5) |
C5—C4—C9—C8 | 0.3 (7) | C36—C35—C38—O8 | −10.6 (7) |
C3—C4—C9—C8 | −179.9 (5) | N2—C11—N1—C7 | −1.5 (8) |
C5—C6—C10—N2 | 169.7 (4) | C8—C7—N1—C11 | −175.0 (5) |
C7—C6—C10—N2 | −11.2 (6) | C6—C7—N1—C11 | 3.9 (7) |
C17—C12—C13—C14 | 2.3 (8) | N1—C11—N2—C12 | 174.6 (5) |
N2—C12—C13—C14 | 178.8 (5) | N1—C11—N2—C10 | −8.1 (8) |
C12—C13—C14—C15 | −0.2 (8) | C13—C12—N2—C11 | 160.4 (5) |
C13—C14—C15—C16 | −1.4 (8) | C17—C12—N2—C11 | −23.2 (7) |
C13—C14—C15—C18 | 179.4 (5) | C13—C12—N2—C10 | −17.0 (7) |
C14—C15—C16—C17 | 0.9 (8) | C17—C12—N2—C10 | 159.5 (4) |
C18—C15—C16—C17 | −180.0 (5) | C6—C10—N2—C11 | 13.4 (6) |
C15—C16—C17—C12 | 1.2 (8) | C6—C10—N2—C12 | −169.2 (4) |
C13—C12—C17—C16 | −2.7 (8) | N4—C31—N3—C27 | 1.9 (8) |
N2—C12—C17—C16 | −179.2 (5) | C28—C27—N3—C31 | 176.9 (5) |
C16—C15—C18—O3 | −172.4 (6) | C26—C27—N3—C31 | −4.8 (7) |
C14—C15—C18—O3 | 6.8 (8) | N3—C31—N4—C32 | −171.8 (5) |
C16—C15—C18—O4 | 6.8 (8) | N3—C31—N4—C30 | 7.5 (8) |
C14—C15—C18—O4 | −174.1 (5) | C37—C32—N4—C31 | 18.1 (8) |
O6—C23—C24—C29 | 163.0 (6) | C33—C32—N4—C31 | −162.7 (5) |
O5—C23—C24—C29 | −16.9 (8) | C37—C32—N4—C30 | −161.2 (5) |
O6—C23—C24—C25 | −18.4 (9) | C33—C32—N4—C30 | 18.0 (7) |
O5—C23—C24—C25 | 161.7 (4) | C26—C30—N4—C31 | −12.4 (6) |
C29—C24—C25—C26 | −0.1 (7) | C26—C30—N4—C32 | 166.9 (4) |
C23—C24—C25—C26 | −178.8 (5) | O2—C3—O1—C2 | 2.0 (8) |
C24—C25—C26—C27 | 0.9 (7) | C4—C3—O1—C2 | 178.9 (4) |
C24—C25—C26—C30 | −178.0 (5) | C1—C2—O1—C3 | −179.3 (4) |
C25—C26—C27—C28 | −2.2 (6) | O3—C18—O4—C19 | −3.3 (9) |
C30—C26—C27—C28 | 176.8 (5) | C15—C18—O4—C19 | 177.6 (4) |
C25—C26—C27—N3 | 179.5 (5) | C20—C19—O4—C18 | 143.2 (5) |
C30—C26—C27—N3 | −1.5 (6) | O6—C23—O5—C22 | 1.0 (8) |
C26—C27—C28—C29 | 2.6 (7) | C24—C23—O5—C22 | −179.1 (4) |
N3—C27—C28—C29 | −179.0 (4) | C21—C22—O5—C23 | 178.2 (5) |
C27—C28—C29—C24 | −1.8 (8) | O7—C38—O8—C39 | −3.0 (8) |
C25—C24—C29—C28 | 0.5 (8) | C35—C38—O8—C39 | 175.1 (4) |
C23—C24—C29—C28 | 179.1 (5) | C40—C39—O8—C38 | 179.7 (5) |