Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601631X/ww2009sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680601631X/ww2009Isup2.hkl |
CCDC reference: 610925
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C13H9NO5 | F(000) = 1072 |
Mr = 259.21 | Dx = 1.488 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 11.868 (2) Å | θ = 10–13° |
b = 10.254 (2) Å | µ = 0.12 mm−1 |
c = 19.833 (4) Å | T = 293 K |
β = 106.51 (3)° | Prism, colourless |
V = 2314.1 (8) Å3 | 0.40 × 0.30 × 0.30 mm |
Z = 8 |
Enraf–Nonius CAD-4 diffractometer | 3113 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.000 |
Graphite monochromator | θmax = 26.0°, θmin = 1.8° |
ω/2θ scans | h = −14→14 |
Absorption correction: ψ scan (SADABS; Sheldrick, 1996) | k = 0→12 |
Tmin = 0.955, Tmax = 0.966 | l = 0→24 |
4544 measured reflections | 3 standard reflections every 200 reflections |
4544 independent reflections | intensity decay: none |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.164 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1P)2] where P = (Fo2 + 2Fc2)/3 |
4544 reflections | (Δ/σ)max < 0.001 |
343 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.27 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 > 2σ(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 | 0.13009 (18) | 0.34520 (17) | 0.27904 (10) | 0.0675 (5) | |
O2 | 0.3903 (3) | 0.1591 (3) | 0.09776 (14) | 0.1127 (9) | |
O3 | 0.39428 (16) | 0.17170 (19) | 0.20815 (11) | 0.0656 (5) | |
O4 | 0.40750 (18) | 0.1870 (2) | 0.31999 (11) | 0.0871 (7) | |
O5 | 0.23037 (18) | −0.06142 (18) | 0.36754 (11) | 0.0731 (6) | |
N1 | 0.17781 (17) | 0.12910 (18) | 0.30494 (10) | 0.0462 (5) | |
C1 | 0.0608 (3) | 0.1735 (4) | 0.50630 (15) | 0.0786 (10) | |
H1A | 0.0463 | 0.1522 | 0.5486 | 0.094* | |
C2 | 0.0276 (3) | 0.2937 (4) | 0.47704 (16) | 0.0742 (9) | |
H2A | −0.0094 | 0.3517 | 0.4998 | 0.089* | |
C3 | 0.0477 (2) | 0.3302 (3) | 0.41519 (13) | 0.0589 (7) | |
H3A | 0.0260 | 0.4122 | 0.3957 | 0.071* | |
C4 | 0.10184 (19) | 0.2400 (2) | 0.38272 (12) | 0.0468 (6) | |
C5 | 0.1355 (2) | 0.1188 (2) | 0.41064 (12) | 0.0500 (6) | |
C6 | 0.1156 (3) | 0.0830 (3) | 0.47405 (13) | 0.0698 (8) | |
H6A | 0.1381 | 0.0016 | 0.4940 | 0.084* | |
C7 | 0.1348 (2) | 0.2513 (2) | 0.31662 (12) | 0.0462 (5) | |
C8 | 0.1870 (2) | 0.0453 (2) | 0.36234 (13) | 0.0502 (6) | |
C9 | 0.2272 (2) | 0.0974 (2) | 0.24800 (12) | 0.0478 (6) | |
H9A | 0.2377 | 0.0025 | 0.2489 | 0.057* | |
C10 | 0.1508 (2) | 0.1316 (3) | 0.17571 (12) | 0.0620 (7) | |
H10A | 0.1342 | 0.2244 | 0.1730 | 0.074* | |
H10B | 0.0768 | 0.0850 | 0.1660 | 0.074* | |
C11 | 0.2139 (3) | 0.0948 (3) | 0.12229 (13) | 0.0678 (8) | |
H11A | 0.2153 | 0.0005 | 0.1188 | 0.081* | |
H11B | 0.1697 | 0.1283 | 0.0767 | 0.081* | |
C12 | 0.3356 (3) | 0.1438 (3) | 0.13860 (16) | 0.0683 (8) | |
C13 | 0.3481 (2) | 0.1567 (2) | 0.26287 (14) | 0.0524 (6) | |
O6 | 0.65068 (16) | 0.95665 (15) | 0.28435 (9) | 0.0565 (5) | |
O7 | 0.92493 (18) | 0.89639 (18) | 0.10274 (10) | 0.0689 (5) | |
O8 | 0.92227 (14) | 0.91002 (15) | 0.21244 (8) | 0.0506 (4) | |
O9 | 0.92416 (15) | 0.93506 (17) | 0.32251 (9) | 0.0598 (5) | |
O10 | 0.81155 (14) | 0.56524 (14) | 0.37181 (8) | 0.0477 (4) | |
N2 | 0.74502 (15) | 0.75916 (16) | 0.31498 (9) | 0.0397 (4) | |
C14 | 0.5281 (3) | 0.8354 (3) | 0.46956 (15) | 0.0638 (7) | |
H14A | 0.4765 | 0.8764 | 0.4903 | 0.077* | |
C15 | 0.5502 (2) | 0.8913 (2) | 0.41159 (14) | 0.0552 (6) | |
H15A | 0.5150 | 0.9695 | 0.3930 | 0.066* | |
C16 | 0.62691 (18) | 0.8264 (2) | 0.38203 (11) | 0.0414 (5) | |
C17 | 0.67791 (18) | 0.7089 (2) | 0.40970 (11) | 0.0394 (5) | |
C18 | 0.6568 (2) | 0.6541 (2) | 0.46829 (11) | 0.0476 (6) | |
H18A | 0.6922 | 0.5763 | 0.4871 | 0.057* | |
C19 | 0.5809 (2) | 0.7193 (3) | 0.49799 (13) | 0.0601 (7) | |
H19A | 0.5650 | 0.6849 | 0.5377 | 0.072* | |
C20 | 0.67036 (19) | 0.8613 (2) | 0.32148 (12) | 0.0423 (5) | |
C21 | 0.75388 (18) | 0.6628 (2) | 0.36660 (11) | 0.0372 (5) | |
C22 | 0.80799 (18) | 0.7553 (2) | 0.26206 (11) | 0.0363 (5) | |
H22A | 0.8576 | 0.6772 | 0.2706 | 0.044* | |
C23 | 0.72631 (19) | 0.7462 (2) | 0.18775 (11) | 0.0450 (5) | |
H23A | 0.6794 | 0.6674 | 0.1827 | 0.054* | |
H23B | 0.6736 | 0.8205 | 0.1782 | 0.054* | |
C24 | 0.7994 (2) | 0.7441 (2) | 0.13635 (12) | 0.0527 (6) | |
H24A | 0.8420 | 0.6622 | 0.1415 | 0.063* | |
H24B | 0.7471 | 0.7476 | 0.0889 | 0.063* | |
C25 | 0.8842 (2) | 0.8526 (2) | 0.14615 (12) | 0.0476 (6) | |
C26 | 0.88777 (19) | 0.8727 (2) | 0.27010 (12) | 0.0410 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0934 (14) | 0.0478 (11) | 0.0666 (12) | 0.0022 (9) | 0.0310 (11) | 0.0087 (9) |
O2 | 0.146 (2) | 0.114 (2) | 0.118 (2) | 0.0114 (17) | 0.103 (2) | 0.0078 (16) |
O3 | 0.0554 (10) | 0.0679 (12) | 0.0851 (14) | −0.0046 (9) | 0.0385 (10) | 0.0068 (10) |
O4 | 0.0639 (12) | 0.1129 (18) | 0.0774 (14) | −0.0293 (12) | 0.0089 (11) | −0.0128 (13) |
O5 | 0.0813 (13) | 0.0476 (11) | 0.0898 (14) | 0.0050 (10) | 0.0234 (11) | 0.0098 (10) |
N1 | 0.0514 (11) | 0.0430 (10) | 0.0502 (11) | −0.0031 (8) | 0.0243 (9) | −0.0033 (9) |
C1 | 0.079 (2) | 0.121 (3) | 0.0445 (14) | −0.051 (2) | 0.0308 (14) | −0.0244 (18) |
C2 | 0.0603 (17) | 0.104 (3) | 0.0662 (18) | −0.0296 (17) | 0.0311 (15) | −0.0350 (18) |
C3 | 0.0481 (13) | 0.0722 (17) | 0.0596 (15) | −0.0111 (12) | 0.0202 (12) | −0.0209 (13) |
C4 | 0.0428 (12) | 0.0535 (14) | 0.0451 (12) | −0.0120 (10) | 0.0141 (10) | −0.0078 (11) |
C5 | 0.0481 (13) | 0.0585 (15) | 0.0435 (13) | −0.0191 (11) | 0.0129 (10) | −0.0026 (11) |
C6 | 0.0773 (19) | 0.083 (2) | 0.0473 (14) | −0.0356 (16) | 0.0154 (14) | 0.0036 (14) |
C7 | 0.0482 (13) | 0.0434 (13) | 0.0496 (13) | −0.0058 (10) | 0.0180 (10) | −0.0021 (11) |
C8 | 0.0498 (13) | 0.0413 (13) | 0.0574 (14) | −0.0097 (11) | 0.0117 (11) | 0.0035 (11) |
C9 | 0.0488 (13) | 0.0461 (13) | 0.0538 (13) | −0.0070 (10) | 0.0228 (11) | −0.0085 (11) |
C10 | 0.0483 (14) | 0.085 (2) | 0.0520 (14) | −0.0044 (13) | 0.0127 (12) | −0.0123 (14) |
C11 | 0.084 (2) | 0.0734 (19) | 0.0482 (14) | 0.0105 (16) | 0.0224 (14) | −0.0053 (14) |
C12 | 0.089 (2) | 0.0569 (16) | 0.078 (2) | 0.0159 (15) | 0.0547 (18) | 0.0098 (14) |
C13 | 0.0468 (13) | 0.0518 (15) | 0.0612 (15) | −0.0046 (11) | 0.0198 (12) | −0.0005 (12) |
O6 | 0.0732 (11) | 0.0347 (9) | 0.0709 (11) | 0.0105 (8) | 0.0355 (9) | 0.0130 (8) |
O7 | 0.0841 (13) | 0.0668 (12) | 0.0733 (12) | 0.0193 (10) | 0.0509 (11) | 0.0270 (10) |
O8 | 0.0541 (9) | 0.0448 (9) | 0.0605 (10) | −0.0079 (7) | 0.0285 (8) | 0.0050 (8) |
O9 | 0.0620 (11) | 0.0578 (11) | 0.0597 (10) | −0.0155 (9) | 0.0172 (9) | −0.0167 (9) |
O10 | 0.0586 (10) | 0.0357 (8) | 0.0524 (9) | 0.0085 (7) | 0.0214 (8) | 0.0047 (7) |
N2 | 0.0484 (10) | 0.0317 (9) | 0.0455 (10) | 0.0034 (8) | 0.0237 (8) | 0.0033 (8) |
C14 | 0.0693 (17) | 0.0637 (17) | 0.0745 (18) | −0.0039 (14) | 0.0467 (15) | −0.0155 (14) |
C15 | 0.0574 (14) | 0.0469 (13) | 0.0702 (16) | 0.0027 (11) | 0.0326 (13) | −0.0081 (12) |
C16 | 0.0439 (12) | 0.0356 (11) | 0.0493 (12) | −0.0050 (9) | 0.0205 (10) | −0.0065 (10) |
C17 | 0.0438 (11) | 0.0349 (11) | 0.0419 (11) | −0.0094 (9) | 0.0159 (9) | −0.0054 (9) |
C18 | 0.0589 (14) | 0.0470 (13) | 0.0412 (12) | −0.0114 (11) | 0.0209 (11) | −0.0026 (10) |
C19 | 0.0719 (17) | 0.0667 (17) | 0.0524 (14) | −0.0161 (14) | 0.0351 (13) | −0.0073 (13) |
C20 | 0.0453 (12) | 0.0337 (11) | 0.0521 (13) | 0.0003 (9) | 0.0207 (10) | −0.0011 (10) |
C21 | 0.0407 (11) | 0.0306 (10) | 0.0403 (11) | −0.0050 (9) | 0.0115 (9) | −0.0005 (9) |
C22 | 0.0418 (11) | 0.0308 (10) | 0.0407 (11) | 0.0012 (9) | 0.0188 (9) | 0.0023 (9) |
C23 | 0.0464 (12) | 0.0411 (12) | 0.0481 (13) | −0.0066 (10) | 0.0145 (10) | −0.0030 (10) |
C24 | 0.0658 (15) | 0.0507 (14) | 0.0437 (13) | 0.0007 (12) | 0.0190 (11) | −0.0027 (11) |
C25 | 0.0533 (13) | 0.0428 (13) | 0.0543 (14) | 0.0150 (10) | 0.0276 (11) | 0.0136 (11) |
C26 | 0.0403 (11) | 0.0372 (11) | 0.0497 (13) | 0.0018 (9) | 0.0194 (10) | 0.0025 (10) |
O1—C7 | 1.209 (3) | O6—C20 | 1.206 (3) |
O2—C12 | 1.184 (3) | O7—C25 | 1.189 (3) |
O3—C13 | 1.356 (3) | O8—C26 | 1.374 (3) |
O3—C12 | 1.387 (4) | O8—C25 | 1.393 (3) |
O4—C13 | 1.193 (3) | O9—C26 | 1.192 (3) |
O5—C8 | 1.202 (3) | O10—C21 | 1.200 (2) |
N1—C7 | 1.397 (3) | N2—C20 | 1.401 (3) |
N1—C8 | 1.405 (3) | N2—C21 | 1.405 (3) |
N1—C9 | 1.449 (3) | N2—C22 | 1.452 (2) |
C1—C2 | 1.371 (5) | C14—C15 | 1.375 (4) |
C1—C6 | 1.389 (5) | C14—C19 | 1.388 (4) |
C1—H1A | 0.9300 | C14—H14A | 0.9300 |
C2—C3 | 1.367 (4) | C15—C16 | 1.385 (3) |
C2—H2A | 0.9300 | C15—H15A | 0.9300 |
C3—C4 | 1.385 (3) | C16—C17 | 1.390 (3) |
C3—H3A | 0.9300 | C16—C20 | 1.479 (3) |
C4—C5 | 1.373 (3) | C17—C18 | 1.376 (3) |
C4—C7 | 1.475 (3) | C17—C21 | 1.485 (3) |
C5—C6 | 1.393 (3) | C18—C19 | 1.380 (3) |
C5—C8 | 1.480 (3) | C18—H18A | 0.9300 |
C6—H6A | 0.9300 | C19—H19A | 0.9300 |
C9—C10 | 1.504 (3) | C22—C26 | 1.512 (3) |
C9—C13 | 1.509 (3) | C22—C23 | 1.519 (3) |
C9—H9A | 0.9800 | C22—H22A | 0.9800 |
C10—C11 | 1.509 (3) | C23—C24 | 1.514 (3) |
C10—H10A | 0.9700 | C23—H23A | 0.9700 |
C10—H10B | 0.9700 | C23—H23B | 0.9700 |
C11—C12 | 1.475 (4) | C24—C25 | 1.476 (3) |
C11—H11A | 0.9700 | C24—H24A | 0.9700 |
C11—H11B | 0.9700 | C24—H24B | 0.9700 |
C13—O3—C12 | 124.7 (2) | C26—O8—C25 | 125.03 (18) |
C7—N1—C8 | 111.22 (19) | C20—N2—C21 | 112.14 (17) |
C7—N1—C9 | 125.32 (19) | C20—N2—C22 | 123.77 (17) |
C8—N1—C9 | 122.6 (2) | C21—N2—C22 | 124.07 (17) |
C2—C1—C6 | 121.4 (3) | C15—C14—C19 | 121.7 (2) |
C2—C1—H1A | 119.3 | C15—C14—H14A | 119.1 |
C6—C1—H1A | 119.3 | C19—C14—H14A | 119.1 |
C3—C2—C1 | 121.6 (3) | C14—C15—C16 | 117.2 (2) |
C3—C2—H2A | 119.2 | C14—C15—H15A | 121.4 |
C1—C2—H2A | 119.2 | C16—C15—H15A | 121.4 |
C2—C3—C4 | 117.2 (3) | C15—C16—C17 | 120.9 (2) |
C2—C3—H3A | 121.4 | C15—C16—C20 | 130.6 (2) |
C4—C3—H3A | 121.4 | C17—C16—C20 | 108.48 (18) |
C5—C4—C3 | 122.5 (2) | C18—C17—C16 | 121.6 (2) |
C5—C4—C7 | 108.0 (2) | C18—C17—C21 | 130.0 (2) |
C3—C4—C7 | 129.5 (2) | C16—C17—C21 | 108.43 (18) |
C4—C5—C6 | 119.9 (3) | C17—C18—C19 | 117.4 (2) |
C4—C5—C8 | 109.0 (2) | C17—C18—H18A | 121.3 |
C6—C5—C8 | 131.1 (3) | C19—C18—H18A | 121.3 |
C1—C6—C5 | 117.5 (3) | C18—C19—C14 | 121.1 (2) |
C1—C6—H6A | 121.3 | C18—C19—H19A | 119.5 |
C5—C6—H6A | 121.3 | C14—C19—H19A | 119.5 |
O1—C7—N1 | 124.5 (2) | O6—C20—N2 | 124.6 (2) |
O1—C7—C4 | 129.2 (2) | O6—C20—C16 | 129.8 (2) |
N1—C7—C4 | 106.19 (19) | N2—C20—C16 | 105.64 (18) |
O5—C8—N1 | 124.0 (2) | O10—C21—N2 | 124.88 (19) |
O5—C8—C5 | 130.8 (2) | O10—C21—C17 | 129.82 (19) |
N1—C8—C5 | 105.2 (2) | N2—C21—C17 | 105.30 (17) |
N1—C9—C10 | 115.0 (2) | N2—C22—C26 | 109.73 (17) |
N1—C9—C13 | 109.26 (19) | N2—C22—C23 | 112.66 (17) |
C10—C9—C13 | 112.0 (2) | C26—C22—C23 | 111.05 (17) |
N1—C9—H9A | 106.7 | N2—C22—H22A | 107.7 |
C10—C9—H9A | 106.7 | C26—C22—H22A | 107.7 |
C13—C9—H9A | 106.7 | C23—C22—H22A | 107.7 |
C9—C10—C11 | 109.1 (2) | C24—C23—C22 | 108.92 (18) |
C9—C10—H10A | 109.9 | C24—C23—H23A | 109.9 |
C11—C10—H10A | 109.9 | C22—C23—H23A | 109.9 |
C9—C10—H10B | 109.9 | C24—C23—H23B | 109.9 |
C11—C10—H10B | 109.9 | C22—C23—H23B | 109.9 |
H10A—C10—H10B | 108.3 | H23A—C23—H23B | 108.3 |
C12—C11—C10 | 114.2 (2) | C25—C24—C23 | 113.57 (19) |
C12—C11—H11A | 108.7 | C25—C24—H24A | 108.9 |
C10—C11—H11A | 108.7 | C23—C24—H24A | 108.9 |
C12—C11—H11B | 108.7 | C25—C24—H24B | 108.9 |
C10—C11—H11B | 108.7 | C23—C24—H24B | 108.9 |
H11A—C11—H11B | 107.6 | H24A—C24—H24B | 107.7 |
O2—C12—O3 | 115.8 (3) | O7—C25—O8 | 115.7 (2) |
O2—C12—C11 | 126.0 (3) | O7—C25—C24 | 126.3 (2) |
O3—C12—C11 | 118.2 (2) | O8—C25—C24 | 117.97 (19) |
O4—C13—O3 | 117.8 (2) | O9—C26—O8 | 117.1 (2) |
O4—C13—C9 | 124.3 (2) | O9—C26—C22 | 125.5 (2) |
O3—C13—C9 | 117.9 (2) | O8—C26—C22 | 117.38 (19) |
C6—C1—C2—C3 | −0.5 (4) | C19—C14—C15—C16 | 0.5 (4) |
C1—C2—C3—C4 | 0.8 (4) | C14—C15—C16—C17 | 0.8 (3) |
C2—C3—C4—C5 | −0.5 (3) | C14—C15—C16—C20 | −178.5 (2) |
C2—C3—C4—C7 | −179.8 (2) | C15—C16—C17—C18 | −1.7 (3) |
C3—C4—C5—C6 | −0.1 (3) | C20—C16—C17—C18 | 177.8 (2) |
C7—C4—C5—C6 | 179.3 (2) | C15—C16—C17—C21 | 179.3 (2) |
C3—C4—C5—C8 | 178.3 (2) | C20—C16—C17—C21 | −1.3 (2) |
C7—C4—C5—C8 | −2.2 (2) | C16—C17—C18—C19 | 1.2 (3) |
C2—C1—C6—C5 | −0.1 (4) | C21—C17—C18—C19 | −180.0 (2) |
C4—C5—C6—C1 | 0.4 (3) | C17—C18—C19—C14 | 0.1 (4) |
C8—C5—C6—C1 | −177.6 (2) | C15—C14—C19—C18 | −1.0 (4) |
C8—N1—C7—O1 | 171.9 (2) | C21—N2—C20—O6 | 178.3 (2) |
C9—N1—C7—O1 | 2.4 (4) | C22—N2—C20—O6 | −0.3 (3) |
C8—N1—C7—C4 | −6.6 (2) | C21—N2—C20—C16 | −0.6 (2) |
C9—N1—C7—C4 | −176.01 (19) | C22—N2—C20—C16 | −179.19 (18) |
C5—C4—C7—O1 | −173.0 (2) | C15—C16—C20—O6 | 1.8 (4) |
C3—C4—C7—O1 | 6.4 (4) | C17—C16—C20—O6 | −177.6 (2) |
C5—C4—C7—N1 | 5.3 (2) | C15—C16—C20—N2 | −179.4 (2) |
C3—C4—C7—N1 | −175.2 (2) | C17—C16—C20—N2 | 1.2 (2) |
C7—N1—C8—O5 | −173.9 (2) | C20—N2—C21—O10 | 179.4 (2) |
C9—N1—C8—O5 | −4.1 (4) | C22—N2—C21—O10 | −2.1 (3) |
C7—N1—C8—C5 | 5.2 (2) | C20—N2—C21—C17 | −0.2 (2) |
C9—N1—C8—C5 | 174.99 (18) | C22—N2—C21—C17 | 178.42 (18) |
C4—C5—C8—O5 | 177.3 (3) | C18—C17—C21—O10 | 2.5 (4) |
C6—C5—C8—O5 | −4.5 (4) | C16—C17—C21—O10 | −178.6 (2) |
C4—C5—C8—N1 | −1.7 (2) | C18—C17—C21—N2 | −178.0 (2) |
C6—C5—C8—N1 | 176.5 (2) | C16—C17—C21—N2 | 0.9 (2) |
C7—N1—C9—C10 | −52.9 (3) | C20—N2—C22—C26 | 59.3 (3) |
C8—N1—C9—C10 | 138.8 (2) | C21—N2—C22—C26 | −119.1 (2) |
C7—N1—C9—C13 | 74.0 (3) | C20—N2—C22—C23 | −64.9 (3) |
C8—N1—C9—C13 | −94.3 (2) | C21—N2—C22—C23 | 116.6 (2) |
N1—C9—C10—C11 | 179.3 (2) | N2—C22—C23—C24 | 179.44 (17) |
C13—C9—C10—C11 | 53.8 (3) | C26—C22—C23—C24 | 55.9 (2) |
C9—C10—C11—C12 | −50.3 (3) | C22—C23—C24—C25 | −52.6 (3) |
C13—O3—C12—O2 | −177.9 (2) | C26—O8—C25—O7 | −178.79 (19) |
C13—O3—C12—C11 | 0.3 (4) | C26—O8—C25—C24 | 0.6 (3) |
C10—C11—C12—O2 | −158.1 (3) | C23—C24—C25—O7 | −155.8 (2) |
C10—C11—C12—O3 | 24.0 (4) | C23—C24—C25—O8 | 24.9 (3) |
C12—O3—C13—O4 | −178.5 (3) | C25—O8—C26—O9 | −176.8 (2) |
C12—O3—C13—C9 | 4.2 (4) | C25—O8—C26—C22 | 3.8 (3) |
N1—C9—C13—O4 | 21.9 (4) | N2—C22—C26—O9 | 22.6 (3) |
C10—C9—C13—O4 | 150.6 (3) | C23—C22—C26—O9 | 147.8 (2) |
N1—C9—C13—O3 | −160.9 (2) | N2—C22—C26—O8 | −158.04 (17) |
C10—C9—C13—O3 | −32.2 (3) | C23—C22—C26—O8 | −32.8 (2) |