Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806011494/wn2014sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806011494/wn2014Isup2.hkl |
CCDC reference: 608524
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C20H28N4O8 | F(000) = 960 |
Mr = 452.46 | Dx = 1.331 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.918 (6) Å | Cell parameters from 952 reflections |
b = 12.090 (6) Å | θ = 2.4–25.1° |
c = 15.488 (8) Å | µ = 0.10 mm−1 |
β = 110.993 (8)° | T = 293 K |
V = 2258 (2) Å3 | Block, colorless |
Z = 4 | 0.38 × 0.36 × 0.34 mm |
Bruker SMART CCD area-detector diffractometer | 4613 independent reflections |
Radiation source: fine-focus sealed tube | 2990 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
φ and ω scans | θmax = 26.4°, θmin = 2.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→15 |
Tmin = 0.903, Tmax = 1.000 | k = −12→15 |
12464 measured reflections | l = −19→13 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.118 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0517P)2 + 0.5195P] where P = (Fo2 + 2Fc2)/3 |
4613 reflections | (Δ/σ)max < 0.001 |
304 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
Experimental. 1H NMR (300 MHz, [D6]DMSO): deta=1.18 (t, J=7.0 Hz, 6H), 1.44 (s, 6H), 2.64 (m, 4H), 3.23 (m, 2H), 3.72 (s, 2H), 3.81 (m, 2H), 4.07 (q, J=7.0 Hz, 4H), 10.34 (s, 2H); 13C NMR (300 MHz, [D6]DMSO): deta=14.05, 23.10, 32.49, 40.35, 48.13, 60.06, 61.69, 150.96, 170.77, 171.24. TOFMS (CI) calcd for (M+) C20H29N4O8: 453.1985, found: 453.1989. |
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 | Occ. (<1) | |
N1 | 0.14325 (12) | 0.28163 (13) | 0.11190 (10) | 0.0336 (4) | |
N2 | 0.07294 (12) | 0.45131 (13) | 0.13842 (11) | 0.0377 (4) | |
H2A | 0.0629 | 0.5198 | 0.1225 | 0.045* | |
N3 | −0.19393 (12) | 0.27695 (13) | 0.15140 (10) | 0.0320 (4) | |
N4 | −0.18893 (12) | 0.35457 (14) | 0.01436 (11) | 0.0376 (4) | |
H4A | −0.2145 | 0.4051 | −0.0269 | 0.045* | |
O1 | 0.20700 (12) | 0.44207 (13) | 0.07575 (11) | 0.0562 (4) | |
O2 | −0.03526 (12) | 0.47539 (12) | 0.22356 (10) | 0.0516 (4) | |
O3 | −0.32706 (11) | 0.39572 (13) | 0.06667 (10) | 0.0499 (4) | |
O4 | −0.06555 (11) | 0.31140 (12) | −0.05270 (9) | 0.0451 (4) | |
O5 | 0.42613 (13) | 0.16069 (13) | 0.28547 (11) | 0.0559 (4) | |
O6 | 0.28324 (13) | 0.05219 (15) | 0.20681 (12) | 0.0713 (5) | |
O7 | −0.44422 (12) | 0.04475 (13) | 0.14332 (12) | 0.0613 (5) | |
O8 | −0.25979 (13) | 0.03946 (14) | 0.18792 (13) | 0.0707 (5) | |
C1 | 0.14510 (15) | 0.39243 (17) | 0.10654 (13) | 0.0365 (5) | |
C2 | 0.01603 (14) | 0.41271 (17) | 0.19230 (13) | 0.0350 (4) | |
C3 | 0.02554 (14) | 0.28993 (15) | 0.21236 (12) | 0.0308 (4) | |
C4 | 0.06520 (14) | 0.22552 (15) | 0.14415 (12) | 0.0318 (4) | |
H4 | 0.0980 | 0.1554 | 0.1729 | 0.038* | |
C5 | −0.05881 (14) | 0.20421 (15) | 0.07982 (12) | 0.0310 (4) | |
C6 | −0.08754 (14) | 0.22644 (15) | 0.16642 (12) | 0.0299 (4) | |
H6 | −0.0836 | 0.1564 | 0.1993 | 0.036* | |
C7 | −0.24164 (15) | 0.34482 (16) | 0.07926 (13) | 0.0342 (4) | |
C8 | −0.10286 (14) | 0.29448 (16) | 0.00837 (12) | 0.0323 (4) | |
C9 | 0.08799 (17) | 0.2723 (2) | 0.31571 (13) | 0.0481 (6) | |
H9A | 0.1596 | 0.3067 | 0.3335 | 0.072* | |
H9B | 0.0969 | 0.1945 | 0.3286 | 0.072* | |
H9C | 0.0467 | 0.3046 | 0.3500 | 0.072* | |
C10 | −0.08983 (18) | 0.09129 (18) | 0.03396 (16) | 0.0505 (6) | |
H10A | −0.1689 | 0.0824 | 0.0122 | 0.076* | |
H10B | −0.0554 | 0.0343 | 0.0781 | 0.076* | |
H10C | −0.0648 | 0.0861 | −0.0172 | 0.076* | |
C11 | 0.20756 (16) | 0.21850 (18) | 0.06763 (13) | 0.0415 (5) | |
H11A | 0.2038 | 0.2556 | 0.0111 | 0.050* | |
H11B | 0.1748 | 0.1457 | 0.0512 | 0.050* | |
C12 | 0.32815 (16) | 0.20599 (19) | 0.12987 (15) | 0.0456 (5) | |
H12A | 0.3700 | 0.1765 | 0.0941 | 0.055* | |
H12B | 0.3583 | 0.2782 | 0.1529 | 0.055* | |
C13 | 0.34127 (16) | 0.13082 (18) | 0.21013 (15) | 0.0442 (5) | |
C14 | 0.4494 (2) | 0.0907 (2) | 0.36797 (17) | 0.0630 (7) | 0.535 (5) |
H14A | 0.5288 | 0.0864 | 0.4011 | 0.076* | 0.535 (5) |
H14B | 0.4218 | 0.0165 | 0.3497 | 0.076* | 0.535 (5) |
C15 | 0.3929 (5) | 0.1404 (4) | 0.4308 (4) | 0.0783 (18) | 0.535 (5) |
H15A | 0.4165 | 0.2156 | 0.4450 | 0.117* | 0.535 (5) |
H15B | 0.4130 | 0.0983 | 0.4870 | 0.117* | 0.535 (5) |
H15C | 0.3139 | 0.1382 | 0.3997 | 0.117* | 0.535 (5) |
C14' | 0.4494 (2) | 0.0907 (2) | 0.36797 (17) | 0.0630 (7) | 0.465 (5) |
H14C | 0.3806 | 0.0648 | 0.3727 | 0.076* | 0.465 (5) |
H14D | 0.4895 | 0.1327 | 0.4232 | 0.076* | 0.465 (5) |
C15' | 0.5185 (4) | −0.0066 (5) | 0.3586 (4) | 0.0661 (18) | 0.465 (5) |
H15D | 0.4760 | −0.0507 | 0.3063 | 0.099* | 0.465 (5) |
H15E | 0.5392 | −0.0508 | 0.4137 | 0.099* | 0.465 (5) |
H15F | 0.5840 | 0.0200 | 0.3498 | 0.099* | 0.465 (5) |
C16 | −0.24076 (16) | 0.27283 (18) | 0.22484 (13) | 0.0405 (5) | |
H16A | −0.2516 | 0.3478 | 0.2423 | 0.049* | |
H16B | −0.1881 | 0.2369 | 0.2787 | 0.049* | |
C17 | −0.35059 (16) | 0.21135 (18) | 0.19642 (16) | 0.0469 (5) | |
H17A | −0.3805 | 0.2189 | 0.2453 | 0.056* | |
H17B | −0.4023 | 0.2462 | 0.1415 | 0.056* | |
C18 | −0.34311 (17) | 0.09051 (19) | 0.17697 (15) | 0.0474 (5) | |
C19 | −0.4493 (2) | −0.0733 (2) | 0.1242 (2) | 0.0781 (8) | |
H19A | −0.4090 | −0.1140 | 0.1802 | 0.094* | |
H19B | −0.4162 | −0.0893 | 0.0784 | 0.094* | |
C20 | −0.5684 (2) | −0.1065 (3) | 0.0888 (2) | 0.0875 (9) | |
H20A | −0.5997 | −0.0926 | 0.1354 | 0.131* | |
H20B | −0.5743 | −0.1839 | 0.0738 | 0.131* | |
H20C | −0.6078 | −0.0644 | 0.0343 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0293 (8) | 0.0359 (10) | 0.0382 (9) | 0.0042 (7) | 0.0152 (7) | 0.0047 (7) |
N2 | 0.0345 (9) | 0.0311 (9) | 0.0487 (10) | 0.0037 (7) | 0.0162 (8) | 0.0060 (7) |
N3 | 0.0266 (8) | 0.0378 (9) | 0.0330 (9) | 0.0045 (7) | 0.0125 (7) | 0.0041 (7) |
N4 | 0.0339 (8) | 0.0427 (10) | 0.0364 (9) | 0.0110 (7) | 0.0127 (7) | 0.0122 (7) |
O1 | 0.0498 (9) | 0.0516 (10) | 0.0805 (11) | 0.0080 (7) | 0.0396 (9) | 0.0247 (8) |
O2 | 0.0554 (9) | 0.0439 (9) | 0.0648 (10) | −0.0008 (7) | 0.0329 (8) | −0.0136 (7) |
O3 | 0.0391 (8) | 0.0594 (10) | 0.0543 (9) | 0.0214 (7) | 0.0205 (7) | 0.0126 (7) |
O4 | 0.0458 (8) | 0.0605 (10) | 0.0330 (7) | 0.0081 (7) | 0.0188 (7) | 0.0021 (7) |
O5 | 0.0551 (10) | 0.0536 (10) | 0.0523 (10) | −0.0057 (8) | 0.0110 (8) | 0.0109 (8) |
O6 | 0.0499 (10) | 0.0648 (12) | 0.0824 (13) | −0.0122 (9) | 0.0035 (9) | 0.0279 (9) |
O7 | 0.0405 (9) | 0.0445 (10) | 0.0980 (13) | −0.0007 (7) | 0.0236 (8) | 0.0025 (9) |
O8 | 0.0405 (9) | 0.0515 (11) | 0.1141 (15) | 0.0092 (8) | 0.0203 (9) | 0.0085 (10) |
C1 | 0.0290 (10) | 0.0394 (12) | 0.0408 (11) | 0.0049 (8) | 0.0121 (9) | 0.0094 (9) |
C2 | 0.0278 (9) | 0.0405 (11) | 0.0342 (10) | −0.0026 (9) | 0.0079 (8) | −0.0037 (9) |
C3 | 0.0266 (9) | 0.0341 (11) | 0.0306 (10) | −0.0001 (8) | 0.0090 (8) | 0.0030 (8) |
C4 | 0.0272 (9) | 0.0313 (11) | 0.0362 (10) | 0.0040 (8) | 0.0106 (8) | 0.0065 (8) |
C5 | 0.0266 (9) | 0.0310 (10) | 0.0356 (10) | 0.0033 (8) | 0.0115 (8) | −0.0016 (8) |
C6 | 0.0264 (9) | 0.0292 (10) | 0.0329 (10) | 0.0021 (8) | 0.0093 (8) | 0.0062 (8) |
C7 | 0.0289 (10) | 0.0373 (11) | 0.0363 (11) | 0.0031 (8) | 0.0116 (8) | 0.0008 (9) |
C8 | 0.0283 (9) | 0.0379 (11) | 0.0279 (10) | −0.0010 (8) | 0.0065 (8) | −0.0055 (8) |
C9 | 0.0396 (11) | 0.0669 (16) | 0.0326 (11) | −0.0044 (11) | 0.0066 (9) | 0.0062 (10) |
C10 | 0.0457 (12) | 0.0388 (13) | 0.0668 (15) | −0.0017 (10) | 0.0200 (11) | −0.0154 (11) |
C11 | 0.0398 (11) | 0.0504 (14) | 0.0375 (11) | 0.0086 (10) | 0.0176 (9) | 0.0022 (9) |
C12 | 0.0345 (11) | 0.0511 (14) | 0.0563 (13) | 0.0110 (10) | 0.0224 (10) | 0.0117 (10) |
C13 | 0.0289 (10) | 0.0436 (13) | 0.0598 (14) | 0.0097 (10) | 0.0156 (10) | 0.0118 (10) |
C14 | 0.0651 (16) | 0.0636 (17) | 0.0525 (15) | 0.0010 (13) | 0.0117 (12) | 0.0145 (12) |
C15 | 0.103 (4) | 0.066 (4) | 0.074 (4) | 0.001 (3) | 0.041 (3) | 0.015 (3) |
C14' | 0.0651 (16) | 0.0636 (17) | 0.0525 (15) | 0.0010 (13) | 0.0117 (12) | 0.0145 (12) |
C15' | 0.056 (3) | 0.073 (4) | 0.061 (4) | 0.006 (3) | 0.012 (3) | 0.018 (3) |
C16 | 0.0394 (11) | 0.0480 (13) | 0.0375 (11) | 0.0022 (9) | 0.0179 (9) | 0.0009 (9) |
C17 | 0.0381 (12) | 0.0509 (14) | 0.0612 (14) | 0.0027 (10) | 0.0293 (11) | 0.0054 (11) |
C18 | 0.0371 (12) | 0.0495 (14) | 0.0578 (14) | 0.0024 (10) | 0.0197 (10) | 0.0132 (11) |
C19 | 0.0594 (16) | 0.0461 (17) | 0.126 (3) | −0.0032 (13) | 0.0294 (16) | 0.0016 (15) |
C20 | 0.0692 (19) | 0.065 (2) | 0.125 (3) | −0.0134 (15) | 0.0300 (18) | −0.0078 (17) |
N1—C1 | 1.343 (3) | C9—H9B | 0.9600 |
N1—C4 | 1.445 (2) | C9—H9C | 0.9600 |
N1—C11 | 1.467 (2) | C10—H10A | 0.9600 |
N2—C2 | 1.376 (2) | C10—H10B | 0.9600 |
N2—C1 | 1.396 (2) | C10—H10C | 0.9600 |
N2—H2A | 0.8600 | C11—C12 | 1.517 (3) |
N3—C7 | 1.345 (2) | C11—H11A | 0.9700 |
N3—C6 | 1.445 (2) | C11—H11B | 0.9700 |
N3—C16 | 1.468 (2) | C12—C13 | 1.500 (3) |
N4—C8 | 1.359 (2) | C12—H12A | 0.9700 |
N4—C7 | 1.407 (2) | C12—H12B | 0.9700 |
N4—H4A | 0.8600 | C14—C15 | 1.532 (5) |
O1—C1 | 1.225 (2) | C14—H14A | 0.9700 |
O2—C2 | 1.216 (2) | C14—H14B | 0.9700 |
O3—C7 | 1.217 (2) | C15—H15A | 0.9600 |
O4—C8 | 1.223 (2) | C15—H15B | 0.9600 |
O5—C13 | 1.333 (3) | C15—H15C | 0.9600 |
O5—C14 | 1.471 (3) | C15'—H15D | 0.9600 |
O6—C13 | 1.200 (3) | C15'—H15E | 0.9600 |
O7—C18 | 1.340 (3) | C15'—H15F | 0.9600 |
O7—C19 | 1.455 (3) | C16—C17 | 1.520 (3) |
O8—C18 | 1.199 (2) | C16—H16A | 0.9700 |
C2—C3 | 1.512 (3) | C16—H16B | 0.9700 |
C3—C9 | 1.527 (3) | C17—C18 | 1.502 (3) |
C3—C4 | 1.540 (3) | C17—H17A | 0.9700 |
C3—C6 | 1.576 (2) | C17—H17B | 0.9700 |
C4—C5 | 1.575 (2) | C19—C20 | 1.491 (4) |
C4—H4 | 0.9800 | C19—H19A | 0.9700 |
C5—C8 | 1.513 (3) | C19—H19B | 0.9700 |
C5—C10 | 1.525 (3) | C20—H20A | 0.9600 |
C5—C6 | 1.538 (2) | C20—H20B | 0.9600 |
C6—H6 | 0.9800 | C20—H20C | 0.9600 |
C9—H9A | 0.9600 | ||
C1—N1—C4 | 121.32 (15) | C5—C10—H10B | 109.5 |
C1—N1—C11 | 117.69 (16) | H10A—C10—H10B | 109.5 |
C4—N1—C11 | 119.98 (16) | C5—C10—H10C | 109.5 |
C2—N2—C1 | 127.65 (17) | H10A—C10—H10C | 109.5 |
C2—N2—H2A | 116.2 | H10B—C10—H10C | 109.5 |
C1—N2—H2A | 116.2 | N1—C11—C12 | 112.29 (17) |
C7—N3—C6 | 121.21 (15) | N1—C11—H11A | 109.1 |
C7—N3—C16 | 118.10 (15) | C12—C11—H11A | 109.1 |
C6—N3—C16 | 119.55 (15) | N1—C11—H11B | 109.1 |
C8—N4—C7 | 128.42 (16) | C12—C11—H11B | 109.1 |
C8—N4—H4A | 115.8 | H11A—C11—H11B | 107.9 |
C7—N4—H4A | 115.8 | C13—C12—C11 | 111.87 (17) |
C13—O5—C14 | 116.91 (18) | C13—C12—H12A | 109.2 |
C18—O7—C19 | 116.79 (18) | C11—C12—H12A | 109.2 |
O1—C1—N1 | 122.78 (18) | C13—C12—H12B | 109.2 |
O1—C1—N2 | 119.97 (19) | C11—C12—H12B | 109.2 |
N1—C1—N2 | 117.25 (16) | H12A—C12—H12B | 107.9 |
O2—C2—N2 | 121.06 (19) | O6—C13—O5 | 123.9 (2) |
O2—C2—C3 | 123.07 (17) | O6—C13—C12 | 124.1 (2) |
N2—C2—C3 | 115.83 (16) | O5—C13—C12 | 112.00 (19) |
C2—C3—C9 | 109.00 (16) | O5—C14—C15 | 109.3 (3) |
C2—C3—C4 | 112.19 (15) | O5—C14—H14A | 109.8 |
C9—C3—C4 | 117.88 (16) | C15—C14—H14A | 109.8 |
C2—C3—C6 | 113.03 (14) | O5—C14—H14B | 109.8 |
C9—C3—C6 | 117.47 (15) | C15—C14—H14B | 109.8 |
C4—C3—C6 | 85.78 (13) | H14A—C14—H14B | 108.3 |
N1—C4—C3 | 116.40 (15) | H15D—C15'—H15E | 109.5 |
N1—C4—C5 | 122.39 (15) | H15D—C15'—H15F | 109.5 |
C3—C4—C5 | 90.22 (13) | H15E—C15'—H15F | 109.5 |
N1—C4—H4 | 108.8 | N3—C16—C17 | 113.15 (17) |
C3—C4—H4 | 108.8 | N3—C16—H16A | 108.9 |
C5—C4—H4 | 108.8 | C17—C16—H16A | 108.9 |
C8—C5—C10 | 109.76 (16) | N3—C16—H16B | 108.9 |
C8—C5—C6 | 111.52 (15) | C17—C16—H16B | 108.9 |
C10—C5—C6 | 117.22 (16) | H16A—C16—H16B | 107.8 |
C8—C5—C4 | 112.06 (15) | C18—C17—C16 | 114.41 (17) |
C10—C5—C4 | 118.63 (15) | C18—C17—H17A | 108.7 |
C6—C5—C4 | 85.89 (13) | C16—C17—H17A | 108.7 |
N3—C6—C5 | 116.51 (14) | C18—C17—H17B | 108.7 |
N3—C6—C3 | 122.77 (15) | C16—C17—H17B | 108.7 |
C5—C6—C3 | 90.26 (13) | H17A—C17—H17B | 107.6 |
N3—C6—H6 | 108.6 | O8—C18—O7 | 122.9 (2) |
C5—C6—H6 | 108.6 | O8—C18—C17 | 126.3 (2) |
C3—C6—H6 | 108.6 | O7—C18—C17 | 110.85 (18) |
O3—C7—N3 | 124.14 (17) | O7—C19—C20 | 107.7 (2) |
O3—C7—N4 | 119.11 (17) | O7—C19—H19A | 110.2 |
N3—C7—N4 | 116.73 (16) | C20—C19—H19A | 110.2 |
O4—C8—N4 | 121.48 (17) | O7—C19—H19B | 110.2 |
O4—C8—C5 | 122.50 (17) | C20—C19—H19B | 110.2 |
N4—C8—C5 | 116.00 (15) | H19A—C19—H19B | 108.5 |
C3—C9—H9A | 109.5 | C19—C20—H20A | 109.5 |
C3—C9—H9B | 109.5 | C19—C20—H20B | 109.5 |
H9A—C9—H9B | 109.5 | H20A—C20—H20B | 109.5 |
C3—C9—H9C | 109.5 | C19—C20—H20C | 109.5 |
H9A—C9—H9C | 109.5 | H20A—C20—H20C | 109.5 |
H9B—C9—H9C | 109.5 | H20B—C20—H20C | 109.5 |
C5—C10—H10A | 109.5 | ||
C4—N1—C1—O1 | −176.76 (17) | C10—C5—C6—C3 | 140.95 (16) |
C11—N1—C1—O1 | −8.3 (3) | C4—C5—C6—C3 | 20.74 (13) |
C4—N1—C1—N2 | 3.6 (3) | C2—C3—C6—N3 | −31.2 (2) |
C11—N1—C1—N2 | 172.08 (15) | C9—C3—C6—N3 | 97.2 (2) |
C2—N2—C1—O1 | −164.87 (18) | C4—C3—C6—N3 | −143.50 (17) |
C2—N2—C1—N1 | 14.8 (3) | C2—C3—C6—C5 | 91.11 (16) |
C1—N2—C2—O2 | 172.13 (18) | C9—C3—C6—C5 | −140.59 (17) |
C1—N2—C2—C3 | −5.6 (3) | C4—C3—C6—C5 | −21.24 (13) |
O2—C2—C3—C9 | −63.8 (2) | C6—N3—C7—O3 | −174.62 (18) |
N2—C2—C3—C9 | 113.88 (18) | C16—N3—C7—O3 | −6.8 (3) |
O2—C2—C3—C4 | 163.75 (17) | C6—N3—C7—N4 | 6.6 (3) |
N2—C2—C3—C4 | −18.6 (2) | C16—N3—C7—N4 | 174.37 (16) |
O2—C2—C3—C6 | 68.8 (2) | C8—N4—C7—O3 | −170.17 (19) |
N2—C2—C3—C6 | −113.55 (17) | C8—N4—C7—N3 | 8.7 (3) |
C1—N1—C4—C3 | −28.0 (2) | C7—N4—C8—O4 | 179.36 (18) |
C11—N1—C4—C3 | 163.74 (15) | C7—N4—C8—C5 | 1.0 (3) |
C1—N1—C4—C5 | 80.6 (2) | C10—C5—C8—O4 | −69.2 (2) |
C11—N1—C4—C5 | −87.6 (2) | C6—C5—C8—O4 | 159.16 (17) |
C2—C3—C4—N1 | 34.4 (2) | C4—C5—C8—O4 | 64.8 (2) |
C9—C3—C4—N1 | −93.5 (2) | C10—C5—C8—N4 | 109.14 (18) |
C6—C3—C4—N1 | 147.57 (15) | C6—C5—C8—N4 | −22.5 (2) |
C2—C3—C4—C5 | −92.46 (16) | C4—C5—C8—N4 | −116.85 (17) |
C9—C3—C4—C5 | 139.68 (17) | C1—N1—C11—C12 | 84.8 (2) |
C6—C3—C4—C5 | 20.71 (12) | C4—N1—C11—C12 | −106.6 (2) |
N1—C4—C5—C8 | −31.6 (2) | N1—C11—C12—C13 | 69.6 (2) |
C3—C4—C5—C8 | 90.32 (16) | C14—O5—C13—O6 | 1.1 (3) |
N1—C4—C5—C10 | 97.9 (2) | C14—O5—C13—C12 | −178.06 (18) |
C3—C4—C5—C10 | −140.14 (17) | C11—C12—C13—O6 | 33.5 (3) |
N1—C4—C5—C6 | −143.18 (17) | C11—C12—C13—O5 | −147.36 (18) |
C3—C4—C5—C6 | −21.25 (13) | C13—O5—C14—C15 | −95.7 (3) |
C7—N3—C6—C5 | −29.3 (2) | C7—N3—C16—C17 | 73.5 (2) |
C16—N3—C6—C5 | 163.07 (16) | C6—N3—C16—C17 | −118.47 (19) |
C7—N3—C6—C3 | 79.8 (2) | N3—C16—C17—C18 | 64.6 (2) |
C16—N3—C6—C3 | −87.8 (2) | C19—O7—C18—O8 | 2.9 (3) |
C8—C5—C6—N3 | 36.0 (2) | C19—O7—C18—C17 | −178.0 (2) |
C10—C5—C6—N3 | −91.7 (2) | C16—C17—C18—O8 | 5.4 (3) |
C4—C5—C6—N3 | 148.12 (16) | C16—C17—C18—O7 | −173.61 (18) |
C8—C5—C6—C3 | −91.36 (16) | C18—O7—C19—C20 | 179.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O4i | 0.86 | 2.32 | 3.148 (3) | 163 |
N4—H4A···O1i | 0.86 | 2.01 | 2.795 (3) | 151 |
Symmetry code: (i) −x, −y+1, −z. |