Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807001432/hb2266sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807001432/hb2266Isup2.hkl |
CCDC reference: 636664
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C16H13NO4 | F(000) = 1184 |
Mr = 283.27 | Dx = 1.407 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 920 reflections |
a = 13.252 (3) Å | θ = 2.3–25.5° |
b = 15.431 (3) Å | µ = 0.10 mm−1 |
c = 13.974 (3) Å | T = 293 K |
β = 110.62 (3)° | Block, yellow |
V = 2674.5 (9) Å3 | 0.20 × 0.20 × 0.10 mm |
Z = 8 |
Bruker SMART CCD diffractometer | 5229 independent reflections |
Radiation source: fine-focus sealed tube | 1760 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
ω scans | θmax = 26.0°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2001) | h = 0→16 |
Tmin = 0.980, Tmax = 0.990 | k = 0→19 |
5459 measured reflections | l = −17→16 |
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)] = 0.088 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.205 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.0598P)2] where P = (Fo2 + 2Fc2)/3 |
5229 reflections | (Δ/σ)max < 0.001 |
381 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.35 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 | ||
C1 | 0.2380 (5) | 0.6687 (4) | 0.8676 (4) | 0.0426 (15) | |
C2 | 0.1471 (5) | 0.6454 (4) | 0.8869 (4) | 0.0559 (18) | |
H2 | 0.1294 | 0.5875 | 0.8909 | 0.067* | |
C3 | 0.0829 (5) | 0.7114 (4) | 0.9002 (5) | 0.0600 (18) | |
H3 | 0.0202 | 0.6977 | 0.9125 | 0.072* | |
C4 | 0.1101 (4) | 0.7974 (4) | 0.8957 (4) | 0.0494 (16) | |
H4 | 0.0665 | 0.8409 | 0.9061 | 0.059* | |
C5 | 0.2031 (4) | 0.8191 (3) | 0.8754 (4) | 0.0381 (15) | |
C6 | 0.2673 (4) | 0.7531 (3) | 0.8622 (4) | 0.0435 (15) | |
H6 | 0.3301 | 0.7659 | 0.8497 | 0.052* | |
C7 | 0.2379 (5) | 0.9113 (4) | 0.8701 (4) | 0.0451 (16) | |
C8 | 0.1657 (4) | 0.9820 (3) | 0.8718 (4) | 0.0448 (16) | |
H8 | 0.1010 | 0.9698 | 0.8811 | 0.054* | |
C9 | 0.1914 (4) | 1.0642 (4) | 0.8602 (4) | 0.0447 (15) | |
H9 | 0.2563 | 1.0727 | 0.8500 | 0.054* | |
C10 | 0.1297 (4) | 1.1419 (4) | 0.8616 (4) | 0.0433 (16) | |
C11 | 0.0288 (5) | 1.1390 (4) | 0.8720 (4) | 0.0477 (16) | |
H11 | −0.0023 | 1.0858 | 0.8764 | 0.057* | |
C12 | −0.0251 (4) | 1.2147 (4) | 0.8757 (4) | 0.0474 (16) | |
H12 | −0.0926 | 1.2121 | 0.8820 | 0.057* | |
C13 | 0.0203 (5) | 1.2943 (4) | 0.8702 (4) | 0.0479 (17) | |
C14 | 0.1195 (5) | 1.2984 (3) | 0.8583 (4) | 0.0460 (16) | |
H14 | 0.1504 | 1.3516 | 0.8534 | 0.055* | |
C15 | 0.1715 (5) | 1.2224 (3) | 0.8538 (4) | 0.0464 (15) | |
H15 | 0.2378 | 1.2253 | 0.8451 | 0.056* | |
C16 | 0.0081 (5) | 1.4486 (3) | 0.8774 (4) | 0.0599 (18) | |
H16A | 0.0742 | 1.4513 | 0.9352 | 0.090* | |
H16B | −0.0405 | 1.4924 | 0.8839 | 0.090* | |
H16C | 0.0230 | 1.4581 | 0.8158 | 0.090* | |
C17 | 0.7407 (4) | 0.8879 (4) | 0.8730 (4) | 0.0426 (15) | |
C18 | 0.6427 (4) | 0.9111 (4) | 0.8789 (4) | 0.0532 (17) | |
H18 | 0.6238 | 0.9691 | 0.8795 | 0.064* | |
C19 | 0.5736 (5) | 0.8463 (4) | 0.8838 (5) | 0.0645 (19) | |
H19 | 0.5065 | 0.8601 | 0.8868 | 0.077* | |
C20 | 0.6043 (5) | 0.7600 (4) | 0.8845 (4) | 0.0520 (17) | |
H20 | 0.5572 | 0.7164 | 0.8878 | 0.062* | |
C21 | 0.7039 (4) | 0.7382 (4) | 0.8802 (4) | 0.0398 (15) | |
C22 | 0.7728 (4) | 0.8040 (3) | 0.8739 (4) | 0.0431 (16) | |
H22 | 0.8398 | 0.7909 | 0.8703 | 0.052* | |
C23 | 0.7407 (5) | 0.6469 (4) | 0.8810 (4) | 0.0454 (16) | |
C24 | 0.6720 (5) | 0.5751 (4) | 0.8868 (4) | 0.0513 (17) | |
H24 | 0.6096 | 0.5876 | 0.9002 | 0.062* | |
C25 | 0.6931 (4) | 0.4932 (4) | 0.8741 (4) | 0.0476 (16) | |
H25 | 0.7567 | 0.4837 | 0.8616 | 0.057* | |
C26 | 0.6321 (5) | 0.4160 (4) | 0.8766 (4) | 0.0453 (16) | |
C27 | 0.5308 (5) | 0.4179 (4) | 0.8891 (4) | 0.0522 (16) | |
H27 | 0.5005 | 0.4710 | 0.8954 | 0.063* | |
C28 | 0.4764 (5) | 0.3433 (4) | 0.8920 (4) | 0.0553 (18) | |
H28 | 0.4108 | 0.3460 | 0.9022 | 0.066* | |
C29 | 0.5187 (5) | 0.2632 (4) | 0.8799 (4) | 0.0484 (17) | |
C30 | 0.6162 (5) | 0.2590 (4) | 0.8667 (4) | 0.0493 (17) | |
H30 | 0.6451 | 0.2057 | 0.8589 | 0.059* | |
C31 | 0.6706 (5) | 0.3341 (4) | 0.8652 (4) | 0.0482 (16) | |
H31 | 0.7366 | 0.3303 | 0.8560 | 0.058* | |
C32 | 0.4996 (5) | 0.1105 (4) | 0.8790 (5) | 0.067 (2) | |
H32A | 0.5161 | 0.1049 | 0.8177 | 0.100* | |
H32B | 0.4480 | 0.0670 | 0.8796 | 0.100* | |
H32C | 0.5642 | 0.1031 | 0.9375 | 0.100* | |
N1 | 0.3068 (4) | 0.5978 (3) | 0.8527 (4) | 0.0544 (14) | |
N2 | 0.8148 (5) | 0.9579 (3) | 0.8701 (4) | 0.0595 (15) | |
O1 | 0.3869 (3) | 0.6181 (3) | 0.8329 (3) | 0.0710 (13) | |
O2 | 0.2810 (4) | 0.5234 (3) | 0.8614 (3) | 0.0753 (14) | |
O3 | 0.3263 (3) | 0.9234 (2) | 0.8638 (3) | 0.0661 (13) | |
O4 | −0.0401 (3) | 1.3648 (2) | 0.8735 (3) | 0.0567 (12) | |
O5 | 0.8996 (4) | 0.9374 (3) | 0.8595 (4) | 0.0894 (17) | |
O6 | 0.7891 (4) | 1.0329 (2) | 0.8778 (3) | 0.0757 (14) | |
O7 | 0.8301 (3) | 0.6321 (2) | 0.8769 (3) | 0.0631 (13) | |
O8 | 0.4557 (3) | 0.1940 (3) | 0.8821 (3) | 0.0655 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.048 (4) | 0.032 (4) | 0.045 (4) | 0.012 (3) | 0.014 (3) | 0.003 (3) |
C2 | 0.058 (4) | 0.040 (4) | 0.074 (5) | −0.005 (3) | 0.029 (4) | 0.009 (3) |
C3 | 0.051 (4) | 0.053 (4) | 0.085 (5) | −0.001 (4) | 0.034 (4) | 0.009 (4) |
C4 | 0.042 (4) | 0.048 (4) | 0.063 (4) | 0.012 (3) | 0.024 (3) | 0.005 (3) |
C5 | 0.032 (3) | 0.038 (3) | 0.041 (4) | 0.001 (3) | 0.008 (3) | −0.002 (3) |
C6 | 0.043 (4) | 0.037 (4) | 0.049 (4) | −0.005 (3) | 0.015 (3) | −0.001 (3) |
C7 | 0.036 (4) | 0.050 (4) | 0.048 (4) | −0.004 (3) | 0.013 (3) | −0.001 (3) |
C8 | 0.037 (4) | 0.034 (3) | 0.063 (4) | 0.002 (3) | 0.017 (3) | −0.003 (3) |
C9 | 0.040 (4) | 0.051 (4) | 0.045 (4) | −0.001 (3) | 0.016 (3) | −0.002 (3) |
C10 | 0.034 (4) | 0.046 (4) | 0.048 (4) | 0.001 (3) | 0.012 (3) | −0.003 (3) |
C11 | 0.044 (4) | 0.033 (3) | 0.064 (4) | −0.003 (3) | 0.017 (3) | −0.001 (3) |
C12 | 0.039 (4) | 0.048 (4) | 0.060 (4) | −0.007 (3) | 0.024 (3) | −0.004 (3) |
C13 | 0.045 (4) | 0.040 (4) | 0.059 (4) | 0.005 (3) | 0.018 (3) | −0.002 (3) |
C14 | 0.056 (4) | 0.029 (3) | 0.055 (4) | 0.000 (3) | 0.023 (3) | −0.001 (3) |
C15 | 0.042 (4) | 0.044 (4) | 0.054 (4) | −0.006 (3) | 0.018 (3) | 0.000 (3) |
C16 | 0.070 (5) | 0.035 (4) | 0.073 (5) | 0.005 (3) | 0.022 (4) | −0.007 (3) |
C17 | 0.035 (3) | 0.038 (4) | 0.051 (4) | 0.000 (3) | 0.010 (3) | 0.002 (3) |
C18 | 0.047 (4) | 0.042 (4) | 0.070 (5) | 0.010 (3) | 0.020 (4) | −0.001 (3) |
C19 | 0.046 (4) | 0.057 (4) | 0.098 (5) | 0.001 (4) | 0.034 (4) | −0.011 (4) |
C20 | 0.048 (4) | 0.050 (4) | 0.062 (4) | −0.002 (3) | 0.024 (3) | 0.003 (3) |
C21 | 0.041 (4) | 0.041 (4) | 0.038 (4) | −0.009 (3) | 0.015 (3) | −0.007 (3) |
C22 | 0.039 (4) | 0.042 (4) | 0.053 (4) | −0.002 (3) | 0.022 (3) | 0.000 (3) |
C23 | 0.060 (4) | 0.033 (4) | 0.044 (4) | −0.001 (3) | 0.019 (3) | −0.006 (3) |
C24 | 0.048 (4) | 0.052 (4) | 0.057 (4) | −0.008 (3) | 0.023 (3) | −0.003 (3) |
C25 | 0.040 (4) | 0.047 (4) | 0.059 (4) | −0.008 (3) | 0.020 (3) | −0.003 (3) |
C26 | 0.050 (4) | 0.034 (4) | 0.052 (4) | 0.002 (3) | 0.017 (3) | 0.002 (3) |
C27 | 0.052 (4) | 0.043 (4) | 0.062 (4) | 0.010 (3) | 0.022 (3) | −0.002 (3) |
C28 | 0.054 (4) | 0.047 (4) | 0.074 (5) | 0.007 (3) | 0.034 (4) | 0.000 (3) |
C29 | 0.054 (4) | 0.031 (4) | 0.059 (4) | 0.004 (3) | 0.019 (4) | 0.002 (3) |
C30 | 0.041 (4) | 0.046 (4) | 0.059 (4) | 0.006 (3) | 0.015 (3) | −0.010 (3) |
C31 | 0.041 (4) | 0.050 (4) | 0.057 (4) | 0.001 (3) | 0.020 (3) | −0.005 (3) |
C32 | 0.064 (5) | 0.047 (4) | 0.084 (5) | −0.006 (4) | 0.020 (4) | −0.002 (4) |
N1 | 0.062 (4) | 0.043 (3) | 0.063 (4) | 0.002 (3) | 0.028 (3) | 0.002 (3) |
N2 | 0.062 (4) | 0.047 (4) | 0.074 (4) | −0.004 (3) | 0.031 (3) | 0.006 (3) |
O1 | 0.070 (3) | 0.047 (3) | 0.112 (4) | 0.008 (2) | 0.051 (3) | 0.000 (2) |
O2 | 0.089 (4) | 0.039 (3) | 0.109 (4) | 0.003 (3) | 0.049 (3) | 0.003 (3) |
O3 | 0.053 (3) | 0.040 (3) | 0.113 (4) | −0.001 (2) | 0.039 (3) | 0.005 (2) |
O4 | 0.056 (3) | 0.037 (2) | 0.080 (3) | 0.003 (2) | 0.028 (2) | −0.002 (2) |
O5 | 0.062 (3) | 0.061 (3) | 0.162 (5) | −0.006 (2) | 0.060 (3) | 0.006 (3) |
O6 | 0.090 (4) | 0.033 (3) | 0.112 (4) | −0.001 (3) | 0.046 (3) | 0.000 (3) |
O7 | 0.053 (3) | 0.047 (3) | 0.101 (3) | 0.004 (2) | 0.041 (3) | −0.003 (2) |
O8 | 0.060 (3) | 0.041 (3) | 0.104 (4) | −0.003 (2) | 0.039 (3) | 0.007 (2) |
C1—C6 | 1.368 (7) | C17—N2 | 1.469 (7) |
C1—C2 | 1.372 (7) | C18—C19 | 1.374 (7) |
C1—N1 | 1.486 (7) | C18—H18 | 0.9300 |
C2—C3 | 1.381 (7) | C19—C20 | 1.392 (7) |
C2—H2 | 0.9300 | C19—H19 | 0.9300 |
C3—C4 | 1.383 (7) | C20—C21 | 1.383 (7) |
C3—H3 | 0.9300 | C20—H20 | 0.9300 |
C4—C5 | 1.399 (7) | C21—C22 | 1.389 (7) |
C4—H4 | 0.9300 | C21—C23 | 1.490 (7) |
C5—C6 | 1.381 (7) | C22—H22 | 0.9300 |
C5—C7 | 1.506 (7) | C23—O7 | 1.227 (6) |
C6—H6 | 0.9300 | C23—C24 | 1.455 (7) |
C7—O3 | 1.219 (6) | C24—C25 | 1.319 (7) |
C7—C8 | 1.457 (7) | C24—H24 | 0.9300 |
C8—C9 | 1.339 (7) | C25—C26 | 1.448 (7) |
C8—H8 | 0.9300 | C25—H25 | 0.9300 |
C9—C10 | 1.455 (7) | C26—C31 | 1.392 (7) |
C9—H9 | 0.9300 | C26—C27 | 1.414 (7) |
C10—C15 | 1.381 (7) | C27—C28 | 1.366 (7) |
C10—C11 | 1.395 (7) | C27—H27 | 0.9300 |
C11—C12 | 1.381 (7) | C28—C29 | 1.392 (7) |
C11—H11 | 0.9300 | C28—H28 | 0.9300 |
C12—C13 | 1.382 (7) | C29—O8 | 1.363 (6) |
C12—H12 | 0.9300 | C29—C30 | 1.368 (7) |
C13—O4 | 1.360 (6) | C30—C31 | 1.370 (7) |
C13—C14 | 1.384 (7) | C30—H30 | 0.9300 |
C14—C15 | 1.372 (7) | C31—H31 | 0.9300 |
C14—H14 | 0.9300 | C32—O8 | 1.421 (6) |
C15—H15 | 0.9300 | C32—H32A | 0.9600 |
C16—O4 | 1.435 (6) | C32—H32B | 0.9600 |
C16—H16A | 0.9600 | C32—H32C | 0.9600 |
C16—H16B | 0.9600 | N1—O2 | 1.216 (5) |
C16—H16C | 0.9600 | N1—O1 | 1.228 (5) |
C17—C22 | 1.362 (7) | N2—O6 | 1.222 (6) |
C17—C18 | 1.377 (7) | N2—O5 | 1.225 (6) |
C6—C1—C2 | 123.2 (6) | C19—C18—H18 | 120.9 |
C6—C1—N1 | 119.5 (6) | C17—C18—H18 | 120.9 |
C2—C1—N1 | 117.3 (5) | C18—C19—C20 | 119.9 (6) |
C1—C2—C3 | 117.2 (6) | C18—C19—H19 | 120.1 |
C1—C2—H2 | 121.4 | C20—C19—H19 | 120.1 |
C3—C2—H2 | 121.4 | C21—C20—C19 | 120.9 (6) |
C2—C3—C4 | 121.3 (6) | C21—C20—H20 | 119.5 |
C2—C3—H3 | 119.4 | C19—C20—H20 | 119.5 |
C4—C3—H3 | 119.4 | C20—C21—C22 | 118.9 (6) |
C3—C4—C5 | 120.1 (6) | C20—C21—C23 | 123.1 (6) |
C3—C4—H4 | 119.9 | C22—C21—C23 | 118.1 (6) |
C5—C4—H4 | 119.9 | C17—C22—C21 | 119.1 (6) |
C6—C5—C4 | 118.6 (5) | C17—C22—H22 | 120.5 |
C6—C5—C7 | 118.5 (5) | C21—C22—H22 | 120.5 |
C4—C5—C7 | 122.9 (5) | O7—C23—C24 | 119.6 (5) |
C1—C6—C5 | 119.6 (6) | O7—C23—C21 | 119.7 (6) |
C1—C6—H6 | 120.2 | C24—C23—C21 | 120.7 (6) |
C5—C6—H6 | 120.2 | C25—C24—C23 | 123.7 (6) |
O3—C7—C8 | 122.8 (6) | C25—C24—H24 | 118.1 |
O3—C7—C5 | 117.8 (6) | C23—C24—H24 | 118.1 |
C8—C7—C5 | 119.4 (5) | C24—C25—C26 | 129.7 (6) |
C9—C8—C7 | 120.7 (6) | C24—C25—H25 | 115.2 |
C9—C8—H8 | 119.7 | C26—C25—H25 | 115.2 |
C7—C8—H8 | 119.7 | C31—C26—C27 | 115.9 (6) |
C8—C9—C10 | 127.6 (6) | C31—C26—C25 | 120.9 (6) |
C8—C9—H9 | 116.2 | C27—C26—C25 | 123.2 (6) |
C10—C9—H9 | 116.2 | C28—C27—C26 | 121.2 (6) |
C15—C10—C11 | 117.6 (6) | C28—C27—H27 | 119.4 |
C15—C10—C9 | 119.8 (5) | C26—C27—H27 | 119.4 |
C11—C10—C9 | 122.6 (5) | C27—C28—C29 | 120.4 (6) |
C12—C11—C10 | 120.3 (6) | C27—C28—H28 | 119.8 |
C12—C11—H11 | 119.9 | C29—C28—H28 | 119.8 |
C10—C11—H11 | 119.9 | O8—C29—C30 | 125.5 (6) |
C11—C12—C13 | 120.6 (6) | O8—C29—C28 | 114.6 (6) |
C11—C12—H12 | 119.7 | C30—C29—C28 | 119.9 (6) |
C13—C12—H12 | 119.7 | C29—C30—C31 | 119.3 (6) |
O4—C13—C12 | 115.8 (6) | C29—C30—H30 | 120.4 |
O4—C13—C14 | 124.3 (6) | C31—C30—H30 | 120.4 |
C12—C13—C14 | 119.9 (6) | C30—C31—C26 | 123.4 (6) |
C15—C14—C13 | 118.7 (6) | C30—C31—H31 | 118.3 |
C15—C14—H14 | 120.7 | C26—C31—H31 | 118.3 |
C13—C14—H14 | 120.7 | O8—C32—H32A | 109.5 |
C14—C15—C10 | 122.9 (6) | O8—C32—H32B | 109.5 |
C14—C15—H15 | 118.5 | H32A—C32—H32B | 109.5 |
C10—C15—H15 | 118.5 | O8—C32—H32C | 109.5 |
O4—C16—H16A | 109.5 | H32A—C32—H32C | 109.5 |
O4—C16—H16B | 109.5 | H32B—C32—H32C | 109.5 |
H16A—C16—H16B | 109.5 | O2—N1—O1 | 124.0 (5) |
O4—C16—H16C | 109.5 | O2—N1—C1 | 118.2 (5) |
H16A—C16—H16C | 109.5 | O1—N1—C1 | 117.8 (5) |
H16B—C16—H16C | 109.5 | O6—N2—O5 | 123.4 (6) |
C22—C17—C18 | 123.0 (6) | O6—N2—C17 | 119.0 (6) |
C22—C17—N2 | 119.3 (5) | O5—N2—C17 | 117.7 (5) |
C18—C17—N2 | 117.6 (6) | C13—O4—C16 | 117.5 (5) |
C19—C18—C17 | 118.2 (6) | C29—O8—C32 | 116.7 (5) |
C6—C1—C2—C3 | 0.7 (9) | C18—C17—C22—C21 | 0.5 (9) |
N1—C1—C2—C3 | −179.7 (5) | N2—C17—C22—C21 | 177.8 (5) |
C1—C2—C3—C4 | −0.9 (10) | C20—C21—C22—C17 | 0.6 (8) |
C2—C3—C4—C5 | 1.2 (9) | C23—C21—C22—C17 | 179.9 (5) |
C3—C4—C5—C6 | −1.3 (8) | C20—C21—C23—O7 | 179.9 (6) |
C3—C4—C5—C7 | −179.5 (5) | C22—C21—C23—O7 | 0.6 (8) |
C2—C1—C6—C5 | −0.8 (9) | C20—C21—C23—C24 | −0.3 (9) |
N1—C1—C6—C5 | 179.6 (5) | C22—C21—C23—C24 | −179.6 (5) |
C4—C5—C6—C1 | 1.0 (8) | O7—C23—C24—C25 | −9.6 (9) |
C7—C5—C6—C1 | 179.4 (5) | C21—C23—C24—C25 | 170.6 (6) |
C6—C5—C7—O3 | −6.6 (8) | C23—C24—C25—C26 | −179.3 (6) |
C4—C5—C7—O3 | 171.7 (5) | C24—C25—C26—C31 | −177.5 (6) |
C6—C5—C7—C8 | 172.9 (5) | C24—C25—C26—C27 | 3.5 (10) |
C4—C5—C7—C8 | −8.8 (8) | C31—C26—C27—C28 | 1.5 (9) |
O3—C7—C8—C9 | 4.1 (9) | C25—C26—C27—C28 | −179.4 (6) |
C5—C7—C8—C9 | −175.4 (5) | C26—C27—C28—C29 | −1.8 (9) |
C7—C8—C9—C10 | −178.9 (5) | C27—C28—C29—O8 | −178.6 (6) |
C8—C9—C10—C15 | 176.5 (6) | C27—C28—C29—C30 | 1.1 (9) |
C8—C9—C10—C11 | −2.7 (9) | O8—C29—C30—C31 | 179.4 (6) |
C15—C10—C11—C12 | −1.0 (9) | C28—C29—C30—C31 | −0.3 (9) |
C9—C10—C11—C12 | 178.2 (5) | C29—C30—C31—C26 | 0.2 (9) |
C10—C11—C12—C13 | −0.6 (9) | C27—C26—C31—C30 | −0.7 (9) |
C11—C12—C13—O4 | 179.4 (5) | C25—C26—C31—C30 | −179.9 (6) |
C11—C12—C13—C14 | 1.6 (9) | C6—C1—N1—O2 | 177.4 (5) |
O4—C13—C14—C15 | −178.6 (5) | C2—C1—N1—O2 | −2.2 (8) |
C12—C13—C14—C15 | −1.0 (9) | C6—C1—N1—O1 | −2.1 (8) |
C13—C14—C15—C10 | −0.6 (9) | C2—C1—N1—O1 | 178.3 (6) |
C11—C10—C15—C14 | 1.6 (9) | C22—C17—N2—O6 | −174.0 (6) |
C9—C10—C15—C14 | −177.6 (5) | C18—C17—N2—O6 | 3.4 (8) |
C22—C17—C18—C19 | −1.3 (9) | C22—C17—N2—O5 | 6.3 (8) |
N2—C17—C18—C19 | −178.6 (5) | C18—C17—N2—O5 | −176.2 (6) |
C17—C18—C19—C20 | 1.0 (9) | C12—C13—O4—C16 | 174.5 (5) |
C18—C19—C20—C21 | 0.1 (10) | C14—C13—O4—C16 | −7.9 (8) |
C19—C20—C21—C22 | −0.9 (9) | C30—C29—O8—C32 | 5.5 (9) |
C19—C20—C21—C23 | 179.8 (6) | C28—C29—O8—C32 | −174.7 (5) |