Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805037050/dn6273sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805037050/dn6273Isup2.hkl |
CCDC reference: 293882
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2000); software used to prepare material for publication: SHELXTL.
C20H32N6O6 | F(000) = 968 |
Mr = 452.52 | Dx = 1.256 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 5173 reflections |
a = 14.6448 (15) Å | θ = 2.3–27.8° |
b = 12.4388 (12) Å | µ = 0.09 mm−1 |
c = 13.2805 (14) Å | T = 292 K |
β = 98.362 (2)° | Block, colourless |
V = 2393.5 (4) Å3 | 0.40 × 0.30 × 0.20 mm |
Z = 4 |
Bruker SMART CCD area-detector diffractometer | 3444 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 25.0°, θmin = 1.4° |
φ and ω scans | h = −16→17 |
11778 measured reflections | k = −11→14 |
4210 independent 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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0815P)2 + 0.5234P] where P = (Fo2 + 2Fc2)/3 |
4210 reflections | (Δ/σ)max = 0.001 |
297 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.20 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 | 0.83215 (16) | 0.4581 (2) | 0.4295 (2) | 0.0888 (8) | |
H1A | 0.8324 | 0.4487 | 0.3578 | 0.133* | |
H1B | 0.8916 | 0.4396 | 0.4657 | 0.133* | |
H1C | 0.8185 | 0.5317 | 0.4430 | 0.133* | |
C2 | 0.7582 (2) | 0.4003 (4) | 0.5777 (2) | 0.1131 (11) | |
H2A | 0.7532 | 0.4754 | 0.5927 | 0.170* | |
H2B | 0.8142 | 0.3721 | 0.6147 | 0.170* | |
H2C | 0.7063 | 0.3625 | 0.5973 | 0.170* | |
C3 | 0.7835 (2) | 0.2693 (2) | 0.4462 (3) | 0.1044 (10) | |
H3A | 0.7342 | 0.2236 | 0.4606 | 0.157* | |
H3B | 0.8392 | 0.2507 | 0.4901 | 0.157* | |
H3C | 0.7925 | 0.2601 | 0.3765 | 0.157* | |
C4 | 0.75919 (15) | 0.38580 (19) | 0.46419 (17) | 0.0659 (6) | |
C5 | 0.61554 (14) | 0.50307 (17) | 0.43265 (15) | 0.0550 (5) | |
H5A | 0.6400 | 0.5278 | 0.5005 | 0.066* | |
H5B | 0.5507 | 0.4866 | 0.4320 | 0.066* | |
C6 | 0.63598 (14) | 0.37425 (14) | 0.30666 (16) | 0.0536 (5) | |
H6A | 0.5729 | 0.3483 | 0.2987 | 0.064* | |
H6B | 0.6748 | 0.3151 | 0.2913 | 0.064* | |
C7 | 0.69046 (13) | 0.66836 (15) | 0.37287 (15) | 0.0508 (5) | |
C8 | 0.71746 (13) | 0.47652 (15) | 0.18419 (14) | 0.0497 (4) | |
C9 | 0.60002 (11) | 0.56193 (13) | 0.25381 (12) | 0.0410 (4) | |
C10 | 0.49423 (12) | 0.56513 (14) | 0.22493 (14) | 0.0467 (4) | |
C11 | 0.36259 (15) | 0.4787 (2) | 0.1400 (2) | 0.0838 (8) | |
H11A | 0.3312 | 0.4874 | 0.1981 | 0.126* | |
H11B | 0.3452 | 0.4113 | 0.1075 | 0.126* | |
H11C | 0.3458 | 0.5364 | 0.0929 | 0.126* | |
C12 | 0.65264 (12) | 0.64724 (14) | 0.19753 (13) | 0.0439 (4) | |
C13 | 0.59147 (12) | 0.71849 (15) | 0.12043 (14) | 0.0464 (4) | |
C14 | 0.48085 (15) | 0.71400 (19) | −0.02712 (16) | 0.0658 (6) | |
H14A | 0.4418 | 0.7588 | 0.0073 | 0.099* | |
H14B | 0.4438 | 0.6621 | −0.0681 | 0.099* | |
H14C | 0.5133 | 0.7577 | −0.0698 | 0.099* | |
C15 | 0.78498 (15) | 0.76223 (18) | 0.26212 (19) | 0.0669 (6) | |
H15A | 0.7725 | 0.8167 | 0.2097 | 0.080* | |
H15B | 0.8139 | 0.7969 | 0.3241 | 0.080* | |
C16 | 0.80235 (14) | 0.63383 (19) | 0.13433 (17) | 0.0646 (6) | |
H16A | 0.7903 | 0.6895 | 0.0830 | 0.078* | |
H16B | 0.8433 | 0.5813 | 0.1107 | 0.078* | |
C17 | 0.94283 (16) | 0.7210 (3) | 0.2276 (2) | 0.0942 (9) | |
C18 | 0.9999 (2) | 0.6272 (4) | 0.1981 (4) | 0.1483 (17) | |
H18A | 0.9912 | 0.5662 | 0.2400 | 0.222* | |
H18B | 1.0639 | 0.6468 | 0.2076 | 0.222* | |
H18C | 0.9805 | 0.6092 | 0.1279 | 0.222* | |
C19 | 0.9458 (2) | 0.8134 (3) | 0.1522 (3) | 0.1391 (17) | |
H19A | 0.9204 | 0.7897 | 0.0851 | 0.209* | |
H19B | 1.0085 | 0.8357 | 0.1525 | 0.209* | |
H19C | 0.9102 | 0.8727 | 0.1717 | 0.209* | |
C20 | 0.9822 (2) | 0.7592 (4) | 0.3345 (3) | 0.1467 (17) | |
H20A | 0.9484 | 0.8210 | 0.3518 | 0.220* | |
H20B | 1.0460 | 0.7779 | 0.3363 | 0.220* | |
H20C | 0.9769 | 0.7026 | 0.3825 | 0.220* | |
N1 | 0.66325 (11) | 0.40597 (13) | 0.41153 (12) | 0.0532 (4) | |
N2 | 0.62353 (10) | 0.59089 (12) | 0.35964 (11) | 0.0456 (4) | |
N3 | 0.64217 (10) | 0.46123 (11) | 0.23258 (11) | 0.0446 (4) | |
N4 | 0.69911 (11) | 0.71167 (12) | 0.27947 (12) | 0.0507 (4) | |
N5 | 0.71602 (10) | 0.58219 (13) | 0.14928 (12) | 0.0504 (4) | |
N6 | 0.84655 (11) | 0.68123 (15) | 0.23076 (14) | 0.0652 (5) | |
O1 | 0.73199 (11) | 0.69780 (13) | 0.45408 (11) | 0.0714 (4) | |
O2 | 0.77349 (11) | 0.40908 (12) | 0.16918 (12) | 0.0710 (4) | |
O3 | 0.45034 (10) | 0.63920 (12) | 0.24816 (13) | 0.0712 (4) | |
O4 | 0.46132 (9) | 0.48030 (11) | 0.17243 (12) | 0.0611 (4) | |
O5 | 0.58570 (10) | 0.81389 (11) | 0.12794 (11) | 0.0617 (4) | |
O6 | 0.54676 (9) | 0.65869 (10) | 0.04739 (10) | 0.0563 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0515 (13) | 0.0943 (19) | 0.118 (2) | 0.0021 (12) | 0.0029 (13) | 0.0223 (16) |
C2 | 0.088 (2) | 0.176 (3) | 0.0685 (18) | 0.019 (2) | −0.0113 (14) | 0.0122 (19) |
C3 | 0.0830 (18) | 0.0773 (18) | 0.143 (3) | 0.0235 (15) | −0.0159 (18) | 0.0167 (18) |
C4 | 0.0559 (12) | 0.0700 (14) | 0.0688 (14) | 0.0059 (10) | −0.0003 (10) | 0.0123 (11) |
C5 | 0.0550 (11) | 0.0643 (12) | 0.0479 (10) | 0.0017 (9) | 0.0155 (8) | 0.0057 (9) |
C6 | 0.0531 (11) | 0.0393 (10) | 0.0679 (13) | −0.0001 (8) | 0.0068 (9) | 0.0021 (8) |
C7 | 0.0505 (10) | 0.0482 (10) | 0.0528 (11) | 0.0028 (8) | 0.0042 (8) | −0.0111 (8) |
C8 | 0.0498 (10) | 0.0524 (11) | 0.0472 (10) | 0.0077 (8) | 0.0080 (8) | −0.0063 (8) |
C9 | 0.0421 (9) | 0.0386 (9) | 0.0422 (9) | 0.0009 (7) | 0.0058 (7) | −0.0026 (7) |
C10 | 0.0424 (10) | 0.0430 (10) | 0.0553 (11) | 0.0012 (8) | 0.0085 (8) | 0.0010 (8) |
C11 | 0.0495 (12) | 0.0768 (16) | 0.120 (2) | −0.0115 (11) | −0.0068 (13) | −0.0117 (14) |
C12 | 0.0405 (9) | 0.0435 (9) | 0.0472 (10) | −0.0001 (7) | 0.0050 (7) | −0.0008 (7) |
C13 | 0.0413 (9) | 0.0474 (11) | 0.0514 (11) | 0.0006 (8) | 0.0095 (8) | 0.0042 (8) |
C14 | 0.0616 (13) | 0.0745 (14) | 0.0572 (12) | 0.0092 (11) | −0.0054 (10) | 0.0053 (10) |
C15 | 0.0540 (12) | 0.0611 (13) | 0.0815 (15) | −0.0161 (10) | −0.0034 (11) | 0.0121 (11) |
C16 | 0.0482 (11) | 0.0800 (15) | 0.0683 (14) | 0.0082 (10) | 0.0174 (10) | 0.0269 (11) |
C17 | 0.0443 (12) | 0.128 (2) | 0.116 (2) | −0.0118 (14) | −0.0009 (13) | 0.0453 (18) |
C18 | 0.0461 (15) | 0.169 (4) | 0.201 (5) | 0.020 (2) | 0.024 (2) | 0.033 (3) |
C19 | 0.0705 (18) | 0.168 (4) | 0.178 (4) | −0.038 (2) | 0.013 (2) | 0.086 (3) |
C20 | 0.0639 (18) | 0.200 (4) | 0.152 (3) | −0.038 (2) | −0.032 (2) | 0.029 (3) |
N1 | 0.0503 (9) | 0.0531 (9) | 0.0557 (10) | 0.0022 (7) | 0.0063 (7) | 0.0088 (7) |
N2 | 0.0482 (8) | 0.0451 (8) | 0.0442 (8) | 0.0013 (6) | 0.0086 (6) | −0.0051 (6) |
N3 | 0.0458 (8) | 0.0395 (8) | 0.0486 (8) | 0.0029 (6) | 0.0072 (6) | −0.0048 (6) |
N4 | 0.0484 (8) | 0.0465 (9) | 0.0553 (9) | −0.0088 (7) | 0.0014 (7) | −0.0005 (7) |
N5 | 0.0441 (8) | 0.0582 (9) | 0.0505 (9) | 0.0073 (7) | 0.0121 (7) | 0.0049 (7) |
N6 | 0.0421 (9) | 0.0771 (12) | 0.0745 (12) | −0.0037 (8) | 0.0023 (8) | 0.0255 (10) |
O1 | 0.0787 (10) | 0.0767 (10) | 0.0549 (9) | −0.0091 (8) | −0.0035 (7) | −0.0213 (7) |
O2 | 0.0698 (10) | 0.0650 (9) | 0.0828 (11) | 0.0218 (8) | 0.0262 (8) | −0.0074 (8) |
O3 | 0.0493 (8) | 0.0634 (9) | 0.1001 (12) | 0.0105 (7) | 0.0083 (8) | −0.0153 (8) |
O4 | 0.0454 (7) | 0.0535 (8) | 0.0811 (10) | −0.0046 (6) | −0.0021 (6) | −0.0103 (7) |
O5 | 0.0631 (9) | 0.0462 (8) | 0.0736 (10) | 0.0054 (6) | 0.0030 (7) | 0.0051 (6) |
O6 | 0.0583 (8) | 0.0540 (8) | 0.0529 (8) | 0.0040 (6) | −0.0046 (6) | 0.0017 (6) |
C1—C4 | 1.519 (3) | C11—H11A | 0.9600 |
C1—H1A | 0.9600 | C11—H11B | 0.9600 |
C1—H1B | 0.9600 | C11—H11C | 0.9600 |
C1—H1C | 0.9600 | C12—N4 | 1.440 (2) |
C2—C4 | 1.520 (4) | C12—N5 | 1.449 (2) |
C2—H2A | 0.9600 | C12—C13 | 1.539 (2) |
C2—H2B | 0.9600 | C13—O5 | 1.195 (2) |
C2—H2C | 0.9600 | C13—O6 | 1.318 (2) |
C3—C4 | 1.519 (4) | C14—O6 | 1.451 (2) |
C3—H3A | 0.9600 | C14—H14A | 0.9600 |
C3—H3B | 0.9600 | C14—H14B | 0.9600 |
C3—H3C | 0.9600 | C14—H14C | 0.9600 |
C4—N1 | 1.497 (3) | C15—N6 | 1.453 (3) |
C5—N1 | 1.443 (3) | C15—N4 | 1.454 (3) |
C5—N2 | 1.477 (2) | C15—H15A | 0.9700 |
C5—H5A | 0.9700 | C15—H15B | 0.9700 |
C5—H5B | 0.9700 | C16—N5 | 1.457 (3) |
C6—N1 | 1.447 (3) | C16—N6 | 1.472 (3) |
C6—N3 | 1.474 (2) | C16—H16A | 0.9700 |
C6—H6A | 0.9700 | C16—H16B | 0.9700 |
C6—H6B | 0.9700 | C17—N6 | 1.501 (3) |
C7—O1 | 1.215 (2) | C17—C18 | 1.520 (5) |
C7—N2 | 1.368 (2) | C17—C20 | 1.528 (5) |
C7—N4 | 1.375 (3) | C17—C19 | 1.529 (4) |
C8—O2 | 1.210 (2) | C18—H18A | 0.9600 |
C8—N3 | 1.368 (2) | C18—H18B | 0.9600 |
C8—N5 | 1.393 (3) | C18—H18C | 0.9600 |
C9—N3 | 1.442 (2) | C19—H19A | 0.9600 |
C9—N2 | 1.443 (2) | C19—H19B | 0.9600 |
C9—C10 | 1.541 (2) | C19—H19C | 0.9600 |
C9—C12 | 1.564 (2) | C20—H20A | 0.9600 |
C10—O3 | 1.189 (2) | C20—H20B | 0.9600 |
C10—O4 | 1.317 (2) | C20—H20C | 0.9600 |
C11—O4 | 1.448 (3) | ||
C4—C1—H1A | 109.5 | O5—C13—C12 | 123.89 (17) |
C4—C1—H1B | 109.5 | O6—C13—C12 | 110.08 (15) |
H1A—C1—H1B | 109.5 | O6—C14—H14A | 109.5 |
C4—C1—H1C | 109.5 | O6—C14—H14B | 109.5 |
H1A—C1—H1C | 109.5 | H14A—C14—H14B | 109.5 |
H1B—C1—H1C | 109.5 | O6—C14—H14C | 109.5 |
C4—C2—H2A | 109.5 | H14A—C14—H14C | 109.5 |
C4—C2—H2B | 109.5 | H14B—C14—H14C | 109.5 |
H2A—C2—H2B | 109.5 | N6—C15—N4 | 109.42 (17) |
C4—C2—H2C | 109.5 | N6—C15—H15A | 109.8 |
H2A—C2—H2C | 109.5 | N4—C15—H15A | 109.8 |
H2B—C2—H2C | 109.5 | N6—C15—H15B | 109.8 |
C4—C3—H3A | 109.5 | N4—C15—H15B | 109.8 |
C4—C3—H3B | 109.5 | H15A—C15—H15B | 108.2 |
H3A—C3—H3B | 109.5 | N5—C16—N6 | 109.79 (16) |
C4—C3—H3C | 109.5 | N5—C16—H16A | 109.7 |
H3A—C3—H3C | 109.5 | N6—C16—H16A | 109.7 |
H3B—C3—H3C | 109.5 | N5—C16—H16B | 109.7 |
N1—C4—C1 | 114.40 (18) | N6—C16—H16B | 109.7 |
N1—C4—C3 | 108.18 (19) | H16A—C16—H16B | 108.2 |
C1—C4—C3 | 109.0 (2) | N6—C17—C18 | 107.9 (3) |
N1—C4—C2 | 107.4 (2) | N6—C17—C20 | 107.8 (2) |
C1—C4—C2 | 109.9 (2) | C18—C17—C20 | 109.3 (3) |
C3—C4—C2 | 107.8 (3) | N6—C17—C19 | 112.5 (2) |
N1—C5—N2 | 113.88 (15) | C18—C17—C19 | 109.8 (3) |
N1—C5—H5A | 108.8 | C20—C17—C19 | 109.4 (3) |
N2—C5—H5A | 108.8 | C17—C18—H18A | 109.5 |
N1—C5—H5B | 108.8 | C17—C18—H18B | 109.5 |
N2—C5—H5B | 108.8 | H18A—C18—H18B | 109.5 |
H5A—C5—H5B | 107.7 | C17—C18—H18C | 109.5 |
N1—C6—N3 | 114.03 (15) | H18A—C18—H18C | 109.5 |
N1—C6—H6A | 108.7 | H18B—C18—H18C | 109.5 |
N3—C6—H6A | 108.7 | C17—C19—H19A | 109.5 |
N1—C6—H6B | 108.7 | C17—C19—H19B | 109.5 |
N3—C6—H6B | 108.7 | H19A—C19—H19B | 109.5 |
H6A—C6—H6B | 107.6 | C17—C19—H19C | 109.5 |
O1—C7—N2 | 125.68 (19) | H19A—C19—H19C | 109.5 |
O1—C7—N4 | 125.66 (19) | H19B—C19—H19C | 109.5 |
N2—C7—N4 | 108.57 (15) | C17—C20—H20A | 109.5 |
O2—C8—N3 | 126.39 (18) | C17—C20—H20B | 109.5 |
O2—C8—N5 | 125.26 (18) | H20A—C20—H20B | 109.5 |
N3—C8—N5 | 108.26 (15) | C17—C20—H20C | 109.5 |
N3—C9—N2 | 111.03 (13) | H20A—C20—H20C | 109.5 |
N3—C9—C10 | 114.65 (14) | H20B—C20—H20C | 109.5 |
N2—C9—C10 | 108.94 (14) | C5—N1—C6 | 109.97 (15) |
N3—C9—C12 | 103.96 (13) | C5—N1—C4 | 119.84 (17) |
N2—C9—C12 | 103.39 (13) | C6—N1—C4 | 120.87 (17) |
C10—C9—C12 | 114.26 (14) | C7—N2—C9 | 111.47 (15) |
O3—C10—O4 | 126.02 (17) | C7—N2—C5 | 124.11 (16) |
O3—C10—C9 | 121.13 (16) | C9—N2—C5 | 115.11 (14) |
O4—C10—C9 | 112.85 (15) | C8—N3—C9 | 111.61 (14) |
O4—C11—H11A | 109.5 | C8—N3—C6 | 123.21 (15) |
O4—C11—H11B | 109.5 | C9—N3—C6 | 115.94 (14) |
H11A—C11—H11B | 109.5 | C7—N4—C12 | 111.61 (14) |
O4—C11—H11C | 109.5 | C7—N4—C15 | 120.50 (16) |
H11A—C11—H11C | 109.5 | C12—N4—C15 | 116.45 (16) |
H11B—C11—H11C | 109.5 | C8—N5—C12 | 111.07 (14) |
N4—C12—N5 | 112.47 (14) | C8—N5—C16 | 119.33 (16) |
N4—C12—C13 | 110.34 (14) | C12—N5—C16 | 116.00 (16) |
N5—C12—C13 | 112.06 (14) | C15—N6—C16 | 108.33 (16) |
N4—C12—C9 | 103.18 (14) | C15—N6—C17 | 113.8 (2) |
N5—C12—C9 | 102.96 (13) | C16—N6—C17 | 113.8 (2) |
C13—C12—C9 | 115.40 (14) | C10—O4—C11 | 116.19 (16) |
O5—C13—O6 | 126.03 (17) | C13—O6—C14 | 116.36 (15) |
N3—C9—C10—O3 | 172.08 (18) | N2—C9—N3—C8 | −103.07 (17) |
N2—C9—C10—O3 | 47.0 (2) | C10—C9—N3—C8 | 132.93 (16) |
C12—C9—C10—O3 | −68.1 (2) | C12—C9—N3—C8 | 7.49 (18) |
N3—C9—C10—O4 | −9.0 (2) | N2—C9—N3—C6 | 44.90 (19) |
N2—C9—C10—O4 | −134.11 (16) | C10—C9—N3—C6 | −79.10 (19) |
C12—C9—C10—O4 | 110.85 (17) | C12—C9—N3—C6 | 155.46 (14) |
N3—C9—C12—N4 | −115.54 (14) | N1—C6—N3—C8 | 94.7 (2) |
N2—C9—C12—N4 | 0.52 (16) | N1—C6—N3—C9 | −49.2 (2) |
C10—C9—C12—N4 | 118.78 (15) | O1—C7—N4—C12 | 170.11 (18) |
N3—C9—C12—N5 | 1.64 (16) | N2—C7—N4—C12 | −13.3 (2) |
N2—C9—C12—N5 | 117.70 (14) | O1—C7—N4—C15 | 28.0 (3) |
C10—C9—C12—N5 | −124.05 (15) | N2—C7—N4—C15 | −155.47 (17) |
N3—C9—C12—C13 | 124.04 (15) | N5—C12—N4—C7 | −102.66 (18) |
N2—C9—C12—C13 | −119.90 (16) | C13—C12—N4—C7 | 131.41 (16) |
C10—C9—C12—C13 | −1.7 (2) | C9—C12—N4—C7 | 7.58 (19) |
N4—C12—C13—O5 | 1.3 (2) | N5—C12—N4—C15 | 41.1 (2) |
N5—C12—C13—O5 | −124.86 (19) | C13—C12—N4—C15 | −84.79 (19) |
C9—C12—C13—O5 | 117.74 (19) | C9—C12—N4—C15 | 151.38 (16) |
N4—C12—C13—O6 | −177.93 (14) | N6—C15—N4—C7 | 87.2 (2) |
N5—C12—C13—O6 | 55.91 (19) | N6—C15—N4—C12 | −53.2 (2) |
C9—C12—C13—O6 | −61.49 (19) | O2—C8—N5—C12 | −168.13 (19) |
N2—C5—N1—C6 | −51.8 (2) | N3—C8—N5—C12 | 15.3 (2) |
N2—C5—N1—C4 | 95.1 (2) | O2—C8—N5—C16 | −29.1 (3) |
N3—C6—N1—C5 | 50.6 (2) | N3—C8—N5—C16 | 154.37 (17) |
N3—C6—N1—C4 | −95.9 (2) | N4—C12—N5—C8 | 100.26 (17) |
C1—C4—N1—C5 | −70.8 (3) | C13—C12—N5—C8 | −134.75 (16) |
C3—C4—N1—C5 | 167.6 (2) | C9—C12—N5—C8 | −10.13 (18) |
C2—C4—N1—C5 | 51.5 (3) | N4—C12—N5—C16 | −40.3 (2) |
C1—C4—N1—C6 | 72.5 (3) | C13—C12—N5—C16 | 84.73 (19) |
C3—C4—N1—C6 | −49.2 (3) | C9—C12—N5—C16 | −150.64 (15) |
C2—C4—N1—C6 | −165.3 (2) | N6—C16—N5—C8 | −85.7 (2) |
O1—C7—N2—C9 | −169.76 (18) | N6—C16—N5—C12 | 51.4 (2) |
N4—C7—N2—C9 | 13.7 (2) | N4—C15—N6—C16 | 61.9 (2) |
O1—C7—N2—C5 | −25.0 (3) | N4—C15—N6—C17 | −170.33 (19) |
N4—C7—N2—C5 | 158.48 (16) | N5—C16—N6—C15 | −61.5 (2) |
N3—C9—N2—C7 | 102.41 (17) | N5—C16—N6—C17 | 170.83 (18) |
C10—C9—N2—C7 | −130.41 (15) | C18—C17—N6—C15 | 177.7 (3) |
C12—C9—N2—C7 | −8.52 (18) | C20—C17—N6—C15 | 59.7 (3) |
N3—C9—N2—C5 | −45.78 (19) | C19—C17—N6—C15 | −61.0 (3) |
C10—C9—N2—C5 | 81.40 (17) | C18—C17—N6—C16 | −57.4 (3) |
C12—C9—N2—C5 | −156.72 (14) | C20—C17—N6—C16 | −175.5 (3) |
N1—C5—N2—C7 | −92.2 (2) | C19—C17—N6—C16 | 63.8 (3) |
N1—C5—N2—C9 | 51.4 (2) | O3—C10—O4—C11 | 0.5 (3) |
O2—C8—N3—C9 | 169.34 (18) | C9—C10—O4—C11 | −178.38 (19) |
N5—C8—N3—C9 | −14.2 (2) | O5—C13—O6—C14 | −3.7 (3) |
O2—C8—N3—C6 | 24.1 (3) | C12—C13—O6—C14 | 175.54 (16) |
N5—C8—N3—C6 | −159.41 (15) |