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
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean (C-C) = 0.008 Å
- R factor = 0.045
- wR factor = 0.095
- Data-to-parameter ratio = 9.0
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.04 Ratio PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.74 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.82 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.21 Ratio PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT432_ALERT_2_C Short Inter X...Y Contact O6 .. C11 .. 2.99 Ang.
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 28.67 From the CIF: _reflns_number_total 4288 Count of symmetry unique reflns 4311 Completeness (_total/calc) 99.47% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
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) |
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