Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680601854X/bt2086sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680601854X/bt2086Isup2.hkl |
CCDC reference: 611202
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXL97.
C30H25N5O4 | F(000) = 1088 |
Mr = 519.55 | Dx = 1.298 Mg m−3 |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 25 reflections |
a = 15.5510 (16) Å | θ = 10–13° |
b = 6.9695 (14) Å | µ = 0.09 mm−1 |
c = 25.220 (2) Å | T = 293 K |
β = 103.46 (3)° | Block, colourless |
V = 2658.3 (7) Å3 | 0.40 × 0.40 × 0.30 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 2200 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
Graphite monochromator | θmax = 26.0°, θmin = 1.7° |
ω/2θ scans | h = −19→19 |
Absorption correction: ψ scan (North et al., 1968) | k = 0→8 |
Tmin = 0.965, Tmax = 0.974 | l = −31→31 |
5676 measured reflections | 3 standard reflections every 200 reflections |
2843 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.044 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.075P)2 + 0.19P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2843 reflections | Δρmax = 0.16 e Å−3 |
353 parameters | Δρmin = −0.15 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0098 (12) |
Experimental. 1H NMR (CDCl3, δ, p.p.m.): 8.16 (m, 1H), 7.74–7.75 (s, 4H), 7.19–7.23 (s, 5H), 7.03–7.05 (s, 2H), 3.74–3.77 (m, 2H), 3.63–3.66 (m, 2H), 2.75 (s, 3H), 2.35 (s, 6H). |
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 | ||
O1 | 0.4685 (2) | 0.7002 (4) | 0.86621 (11) | 0.0787 (9) | |
O2 | 0.78398 (15) | 0.4738 (5) | 0.74647 (13) | 0.0820 (10) | |
O3 | 0.51625 (15) | 0.3550 (4) | 0.70346 (11) | 0.0628 (7) | |
O4 | 0.45346 (15) | 0.9437 (5) | 0.60830 (11) | 0.0723 (9) | |
N1 | 0.5095 (3) | 0.6260 (6) | 0.91871 (15) | 0.0829 (12) | |
N2 | 0.50774 (18) | 0.4057 (5) | 0.85383 (12) | 0.0527 (7) | |
N3 | 0.5157 (2) | 0.9869 (6) | 0.57666 (13) | 0.0743 (11) | |
N4 | 0.57534 (16) | 0.7915 (4) | 0.64624 (11) | 0.0483 (7) | |
N5 | 0.64051 (15) | 0.5322 (4) | 0.74468 (11) | 0.0426 (6) | |
C1 | 0.7061 (3) | −0.0515 (10) | 1.0820 (2) | 0.0994 (17) | |
H1B | 0.6946 | −0.1828 | 1.0711 | 0.149* | |
H1C | 0.6827 | −0.0256 | 1.1133 | 0.149* | |
H1D | 0.7688 | −0.0293 | 1.0911 | 0.149* | |
C2 | 0.6624 (3) | 0.0800 (7) | 1.03555 (19) | 0.0689 (12) | |
C3 | 0.6696 (4) | 0.2766 (8) | 1.0404 (2) | 0.0864 (14) | |
H3B | 0.7040 | 0.3292 | 1.0722 | 0.104* | |
C4 | 0.6278 (4) | 0.3957 (7) | 0.99972 (19) | 0.0870 (15) | |
H4B | 0.6334 | 0.5278 | 1.0046 | 0.104* | |
C5 | 0.5776 (2) | 0.3244 (6) | 0.95161 (15) | 0.0542 (9) | |
C6 | 0.5706 (3) | 0.1281 (6) | 0.94561 (19) | 0.0694 (11) | |
H6A | 0.5374 | 0.0753 | 0.9134 | 0.083* | |
C7 | 0.6129 (3) | 0.0104 (7) | 0.9875 (2) | 0.0861 (15) | |
H7A | 0.6075 | −0.1218 | 0.9828 | 0.103* | |
C8 | 0.5322 (2) | 0.4530 (5) | 0.90796 (15) | 0.0538 (9) | |
C9 | 0.4715 (2) | 0.5622 (5) | 0.83098 (15) | 0.0509 (9) | |
C10 | 0.4321 (2) | 0.6054 (6) | 0.77353 (15) | 0.0558 (9) | |
H10A | 0.3879 | 0.7047 | 0.7719 | 0.067* | |
H10B | 0.4020 | 0.4915 | 0.7564 | 0.067* | |
C11 | 0.49868 (18) | 0.6724 (5) | 0.74004 (13) | 0.0442 (8) | |
C12 | 0.57251 (19) | 0.8004 (5) | 0.77020 (13) | 0.0442 (8) | |
C13 | 0.5681 (2) | 0.9772 (6) | 0.79358 (14) | 0.0531 (9) | |
H13A | 0.5136 | 1.0345 | 0.7922 | 0.064* | |
C14 | 0.6456 (2) | 1.0689 (6) | 0.81915 (15) | 0.0601 (10) | |
H14A | 0.6435 | 1.1888 | 0.8350 | 0.072* | |
C15 | 0.7261 (2) | 0.9816 (6) | 0.82098 (16) | 0.0593 (9) | |
H15A | 0.7779 | 1.0444 | 0.8383 | 0.071* | |
C16 | 0.7320 (2) | 0.8019 (5) | 0.79763 (14) | 0.0493 (8) | |
H16A | 0.7865 | 0.7445 | 0.7990 | 0.059* | |
C17 | 0.65412 (18) | 0.7129 (5) | 0.77239 (12) | 0.0406 (7) | |
C18 | 0.54967 (19) | 0.4971 (5) | 0.72633 (13) | 0.0448 (8) | |
C19 | 0.6825 (3) | 0.2680 (7) | 0.68912 (18) | 0.0757 (13) | |
H19A | 0.7348 | 0.2108 | 0.6819 | 0.114* | |
H19B | 0.6460 | 0.3162 | 0.6557 | 0.114* | |
H19C | 0.6503 | 0.1733 | 0.7043 | 0.114* | |
C20 | 0.7080 (2) | 0.4284 (6) | 0.72852 (15) | 0.0531 (9) | |
C21 | 0.4433 (2) | 0.7608 (6) | 0.68741 (14) | 0.0531 (9) | |
H21A | 0.4003 | 0.6666 | 0.6695 | 0.064* | |
H21B | 0.4108 | 0.8693 | 0.6969 | 0.064* | |
C22 | 0.4952 (2) | 0.8266 (6) | 0.64798 (13) | 0.0488 (8) | |
C23 | 0.5851 (2) | 0.8925 (5) | 0.60135 (12) | 0.0465 (8) | |
C24 | 0.6695 (2) | 0.9026 (5) | 0.58370 (13) | 0.0454 (7) | |
C25 | 0.6728 (2) | 0.9900 (6) | 0.53497 (15) | 0.0600 (10) | |
H25A | 0.6213 | 1.0362 | 0.5120 | 0.072* | |
C26 | 0.7531 (3) | 1.0089 (7) | 0.52035 (17) | 0.0694 (11) | |
H26A | 0.7546 | 1.0681 | 0.4875 | 0.083* | |
C27 | 0.8303 (2) | 0.9420 (5) | 0.55329 (17) | 0.0594 (10) | |
C28 | 0.8259 (2) | 0.8507 (6) | 0.60107 (16) | 0.0605 (10) | |
H28A | 0.8773 | 0.8013 | 0.6234 | 0.073* | |
C29 | 0.7462 (2) | 0.8308 (6) | 0.61666 (14) | 0.0541 (9) | |
H29A | 0.7447 | 0.7693 | 0.6492 | 0.065* | |
C30 | 0.9181 (3) | 0.9625 (8) | 0.5372 (2) | 0.0872 (15) | |
H30A | 0.9643 | 0.9085 | 0.5652 | 0.131* | |
H30B | 0.9300 | 1.0959 | 0.5328 | 0.131* | |
H30C | 0.9153 | 0.8960 | 0.5035 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.121 (2) | 0.0477 (17) | 0.0738 (18) | 0.0228 (17) | 0.0355 (16) | 0.0009 (16) |
O2 | 0.0372 (13) | 0.078 (2) | 0.129 (2) | 0.0161 (14) | 0.0153 (13) | −0.034 (2) |
O3 | 0.0456 (12) | 0.0498 (16) | 0.0893 (18) | 0.0035 (12) | 0.0086 (12) | −0.0164 (15) |
O4 | 0.0526 (13) | 0.092 (2) | 0.0740 (17) | 0.0308 (15) | 0.0173 (12) | 0.0278 (17) |
N1 | 0.135 (3) | 0.049 (2) | 0.068 (2) | 0.012 (2) | 0.031 (2) | −0.0060 (18) |
N2 | 0.0526 (15) | 0.0455 (16) | 0.0627 (18) | 0.0125 (14) | 0.0187 (13) | −0.0005 (15) |
N3 | 0.0621 (18) | 0.092 (3) | 0.071 (2) | 0.029 (2) | 0.0207 (15) | 0.032 (2) |
N4 | 0.0442 (14) | 0.0487 (17) | 0.0521 (15) | 0.0121 (13) | 0.0114 (11) | 0.0080 (14) |
N5 | 0.0352 (12) | 0.0396 (15) | 0.0531 (15) | 0.0107 (12) | 0.0105 (11) | −0.0025 (13) |
C1 | 0.113 (4) | 0.091 (4) | 0.087 (3) | 0.017 (3) | 0.008 (3) | 0.020 (3) |
C2 | 0.069 (3) | 0.071 (3) | 0.068 (3) | 0.007 (2) | 0.019 (2) | 0.009 (2) |
C3 | 0.107 (4) | 0.074 (3) | 0.067 (3) | −0.012 (3) | −0.002 (2) | −0.006 (3) |
C4 | 0.134 (4) | 0.050 (2) | 0.067 (3) | −0.012 (3) | 0.002 (3) | −0.004 (2) |
C5 | 0.061 (2) | 0.047 (2) | 0.058 (2) | −0.0034 (18) | 0.0207 (17) | −0.0037 (18) |
C6 | 0.080 (3) | 0.051 (2) | 0.071 (3) | 0.002 (2) | 0.003 (2) | −0.010 (2) |
C7 | 0.111 (4) | 0.046 (3) | 0.091 (4) | 0.008 (3) | 0.002 (3) | 0.003 (3) |
C8 | 0.060 (2) | 0.044 (2) | 0.063 (2) | −0.0014 (18) | 0.0252 (17) | −0.0040 (18) |
C9 | 0.0471 (17) | 0.049 (2) | 0.065 (2) | 0.0032 (17) | 0.0303 (16) | 0.0028 (19) |
C10 | 0.0386 (16) | 0.057 (2) | 0.075 (2) | 0.0088 (17) | 0.0218 (15) | 0.005 (2) |
C11 | 0.0347 (14) | 0.0447 (19) | 0.0560 (18) | 0.0113 (15) | 0.0160 (13) | 0.0038 (16) |
C12 | 0.0427 (16) | 0.0440 (19) | 0.0504 (17) | 0.0105 (15) | 0.0200 (13) | 0.0024 (16) |
C13 | 0.0532 (18) | 0.046 (2) | 0.066 (2) | 0.0104 (18) | 0.0269 (16) | 0.0005 (19) |
C14 | 0.075 (2) | 0.043 (2) | 0.070 (2) | 0.0036 (19) | 0.0296 (19) | −0.0085 (19) |
C15 | 0.057 (2) | 0.051 (2) | 0.070 (2) | −0.0055 (19) | 0.0159 (17) | −0.010 (2) |
C16 | 0.0412 (16) | 0.046 (2) | 0.061 (2) | 0.0049 (16) | 0.0127 (14) | 0.0000 (18) |
C17 | 0.0386 (15) | 0.0382 (17) | 0.0457 (16) | 0.0081 (14) | 0.0113 (12) | 0.0029 (15) |
C18 | 0.0373 (16) | 0.043 (2) | 0.0529 (19) | 0.0070 (15) | 0.0080 (13) | −0.0011 (17) |
C19 | 0.061 (2) | 0.071 (3) | 0.099 (3) | 0.013 (2) | 0.027 (2) | −0.033 (3) |
C20 | 0.0435 (17) | 0.047 (2) | 0.070 (2) | 0.0163 (16) | 0.0162 (15) | −0.0074 (18) |
C21 | 0.0389 (15) | 0.057 (2) | 0.064 (2) | 0.0146 (16) | 0.0129 (14) | 0.0047 (18) |
C22 | 0.0441 (17) | 0.050 (2) | 0.0498 (18) | 0.0141 (16) | 0.0061 (13) | −0.0001 (17) |
C23 | 0.0450 (16) | 0.0456 (19) | 0.0457 (17) | 0.0089 (16) | 0.0043 (13) | −0.0013 (16) |
C24 | 0.0490 (16) | 0.0389 (18) | 0.0472 (17) | 0.0026 (15) | 0.0089 (13) | −0.0056 (15) |
C25 | 0.059 (2) | 0.057 (2) | 0.064 (2) | 0.008 (2) | 0.0131 (16) | 0.012 (2) |
C26 | 0.077 (2) | 0.056 (2) | 0.082 (3) | 0.002 (2) | 0.032 (2) | 0.017 (2) |
C27 | 0.061 (2) | 0.043 (2) | 0.079 (3) | −0.0052 (18) | 0.0263 (18) | −0.008 (2) |
C28 | 0.0473 (18) | 0.057 (2) | 0.073 (2) | 0.0078 (18) | 0.0059 (16) | −0.009 (2) |
C29 | 0.0523 (18) | 0.054 (2) | 0.0542 (19) | 0.0057 (18) | 0.0091 (15) | 0.0007 (18) |
C30 | 0.072 (2) | 0.070 (3) | 0.132 (4) | −0.013 (3) | 0.051 (3) | −0.011 (3) |
O1—C9 | 1.318 (5) | C11—C21 | 1.533 (4) |
O1—N1 | 1.426 (4) | C11—C18 | 1.539 (5) |
O2—C20 | 1.205 (4) | C12—C13 | 1.374 (5) |
O3—C18 | 1.202 (4) | C12—C17 | 1.397 (4) |
O4—C22 | 1.336 (4) | C13—C14 | 1.384 (5) |
O4—N3 | 1.422 (4) | C13—H13A | 0.9300 |
N1—C8 | 1.303 (5) | C14—C15 | 1.384 (5) |
N2—C9 | 1.299 (5) | C14—H14A | 0.9300 |
N2—C8 | 1.369 (5) | C15—C16 | 1.396 (6) |
N3—C23 | 1.294 (4) | C15—H15A | 0.9300 |
N4—C22 | 1.281 (4) | C16—C17 | 1.378 (4) |
N4—C23 | 1.371 (4) | C16—H16A | 0.9300 |
N5—C18 | 1.402 (4) | C19—C20 | 1.487 (5) |
N5—C20 | 1.410 (4) | C19—H19A | 0.9600 |
N5—C17 | 1.432 (4) | C19—H19B | 0.9600 |
C1—C2 | 1.519 (7) | C19—H19C | 0.9600 |
C1—H1B | 0.9600 | C21—C22 | 1.492 (5) |
C1—H1C | 0.9600 | C21—H21A | 0.9700 |
C1—H1D | 0.9600 | C21—H21B | 0.9700 |
C2—C7 | 1.366 (7) | C23—C24 | 1.482 (4) |
C2—C3 | 1.377 (7) | C24—C29 | 1.380 (4) |
C3—C4 | 1.362 (7) | C24—C25 | 1.384 (5) |
C3—H3B | 0.9300 | C25—C26 | 1.387 (5) |
C4—C5 | 1.374 (6) | C25—H25A | 0.9300 |
C4—H4B | 0.9300 | C26—C27 | 1.373 (6) |
C5—C6 | 1.378 (6) | C26—H26A | 0.9300 |
C5—C8 | 1.467 (5) | C27—C28 | 1.379 (6) |
C6—C7 | 1.377 (6) | C27—C30 | 1.518 (5) |
C6—H6A | 0.9300 | C28—C29 | 1.391 (5) |
C7—H7A | 0.9300 | C28—H28A | 0.9300 |
C9—C10 | 1.467 (5) | C29—H29A | 0.9300 |
C10—C11 | 1.553 (4) | C30—H30A | 0.9600 |
C10—H10A | 0.9700 | C30—H30B | 0.9600 |
C10—H10B | 0.9700 | C30—H30C | 0.9600 |
C11—C12 | 1.512 (5) | ||
C9—O1—N1 | 106.4 (3) | C15—C14—H14A | 120.2 |
C22—O4—N3 | 105.9 (2) | C14—C15—C16 | 121.9 (3) |
C8—N1—O1 | 103.1 (3) | C14—C15—H15A | 119.1 |
C9—N2—C8 | 103.4 (3) | C16—C15—H15A | 119.1 |
C23—N3—O4 | 102.9 (3) | C17—C16—C15 | 117.5 (3) |
C22—N4—C23 | 103.1 (3) | C17—C16—H16A | 121.2 |
C18—N5—C20 | 125.1 (3) | C15—C16—H16A | 121.2 |
C18—N5—C17 | 109.7 (2) | C16—C17—C12 | 121.0 (3) |
C20—N5—C17 | 123.8 (3) | C16—C17—N5 | 129.5 (3) |
C2—C1—H1B | 109.5 | C12—C17—N5 | 109.6 (3) |
C2—C1—H1C | 109.5 | O3—C18—N5 | 126.3 (3) |
H1B—C1—H1C | 109.5 | O3—C18—C11 | 125.1 (3) |
C2—C1—H1D | 109.5 | N5—C18—C11 | 108.6 (3) |
H1B—C1—H1D | 109.5 | C20—C19—H19A | 109.5 |
H1C—C1—H1D | 109.5 | C20—C19—H19B | 109.5 |
C7—C2—C3 | 116.7 (5) | H19A—C19—H19B | 109.5 |
C7—C2—C1 | 122.0 (5) | C20—C19—H19C | 109.5 |
C3—C2—C1 | 121.3 (5) | H19A—C19—H19C | 109.5 |
C4—C3—C2 | 121.7 (5) | H19B—C19—H19C | 109.5 |
C4—C3—H3B | 119.2 | O2—C20—N5 | 119.2 (3) |
C2—C3—H3B | 119.2 | O2—C20—C19 | 122.2 (3) |
C3—C4—C5 | 121.2 (5) | N5—C20—C19 | 118.6 (3) |
C3—C4—H4B | 119.4 | C22—C21—C11 | 114.7 (2) |
C5—C4—H4B | 119.4 | C22—C21—H21A | 108.6 |
C4—C5—C6 | 118.0 (4) | C11—C21—H21A | 108.6 |
C4—C5—C8 | 121.1 (4) | C22—C21—H21B | 108.6 |
C6—C5—C8 | 120.8 (4) | C11—C21—H21B | 108.6 |
C7—C6—C5 | 119.7 (5) | H21A—C21—H21B | 107.6 |
C7—C6—H6A | 120.1 | N4—C22—O4 | 113.4 (3) |
C5—C6—H6A | 120.1 | N4—C22—C21 | 130.3 (3) |
C2—C7—C6 | 122.6 (5) | O4—C22—C21 | 116.3 (3) |
C2—C7—H7A | 118.7 | N3—C23—N4 | 114.7 (3) |
C6—C7—H7A | 118.7 | N3—C23—C24 | 122.0 (3) |
N1—C8—N2 | 113.9 (4) | N4—C23—C24 | 123.2 (3) |
N1—C8—C5 | 121.0 (4) | C29—C24—C25 | 119.2 (3) |
N2—C8—C5 | 125.1 (3) | C29—C24—C23 | 120.3 (3) |
N2—C9—O1 | 113.2 (3) | C25—C24—C23 | 120.5 (3) |
N2—C9—C10 | 130.5 (3) | C24—C25—C26 | 120.0 (3) |
O1—C9—C10 | 116.3 (3) | C24—C25—H25A | 120.0 |
C9—C10—C11 | 114.9 (3) | C26—C25—H25A | 120.0 |
C9—C10—H10A | 108.5 | C27—C26—C25 | 121.4 (4) |
C11—C10—H10A | 108.5 | C27—C26—H26A | 119.3 |
C9—C10—H10B | 108.5 | C25—C26—H26A | 119.3 |
C11—C10—H10B | 108.5 | C26—C27—C28 | 118.1 (3) |
H10A—C10—H10B | 107.5 | C26—C27—C30 | 121.4 (4) |
C12—C11—C21 | 114.0 (3) | C28—C27—C30 | 120.5 (4) |
C12—C11—C18 | 102.2 (2) | C27—C28—C29 | 121.5 (3) |
C21—C11—C18 | 109.8 (3) | C27—C28—H28A | 119.3 |
C12—C11—C10 | 115.4 (3) | C29—C28—H28A | 119.3 |
C21—C11—C10 | 106.3 (2) | C24—C29—C28 | 119.7 (3) |
C18—C11—C10 | 109.1 (3) | C24—C29—H29A | 120.1 |
C13—C12—C17 | 120.6 (3) | C28—C29—H29A | 120.1 |
C13—C12—C11 | 129.6 (3) | C27—C30—H30A | 109.5 |
C17—C12—C11 | 109.8 (3) | C27—C30—H30B | 109.5 |
C12—C13—C14 | 119.3 (3) | H30A—C30—H30B | 109.5 |
C12—C13—H13A | 120.3 | C27—C30—H30C | 109.5 |
C14—C13—H13A | 120.3 | H30A—C30—H30C | 109.5 |
C13—C14—C15 | 119.7 (4) | H30B—C30—H30C | 109.5 |
C13—C14—H14A | 120.2 | ||
C9—O1—N1—C8 | 0.3 (4) | C18—N5—C17—C16 | 178.7 (3) |
C22—O4—N3—C23 | −0.3 (4) | C20—N5—C17—C16 | −13.9 (5) |
C7—C2—C3—C4 | 1.4 (9) | C18—N5—C17—C12 | −2.6 (3) |
C1—C2—C3—C4 | −177.4 (5) | C20—N5—C17—C12 | 164.9 (3) |
C2—C3—C4—C5 | −1.0 (9) | C20—N5—C18—O3 | 15.7 (6) |
C3—C4—C5—C6 | 0.0 (8) | C17—N5—C18—O3 | −177.0 (3) |
C3—C4—C5—C8 | 179.7 (5) | C20—N5—C18—C11 | −164.0 (3) |
C4—C5—C6—C7 | 0.5 (8) | C17—N5—C18—C11 | 3.3 (3) |
C8—C5—C6—C7 | −179.2 (4) | C12—C11—C18—O3 | 177.6 (3) |
C3—C2—C7—C6 | −0.9 (8) | C21—C11—C18—O3 | −61.1 (4) |
C1—C2—C7—C6 | 177.9 (5) | C10—C11—C18—O3 | 55.0 (5) |
C5—C6—C7—C2 | −0.1 (8) | C12—C11—C18—N5 | −2.7 (3) |
O1—N1—C8—N2 | −1.8 (4) | C21—C11—C18—N5 | 118.6 (3) |
O1—N1—C8—C5 | 179.9 (3) | C10—C11—C18—N5 | −125.2 (3) |
C9—N2—C8—N1 | 2.5 (4) | C18—N5—C20—O2 | 178.9 (4) |
C9—N2—C8—C5 | −179.2 (3) | C17—N5—C20—O2 | 13.3 (5) |
C4—C5—C8—N1 | −26.0 (6) | C18—N5—C20—C19 | −0.3 (5) |
C6—C5—C8—N1 | 153.7 (4) | C17—N5—C20—C19 | −165.8 (3) |
C4—C5—C8—N2 | 155.8 (4) | C12—C11—C21—C22 | 54.5 (4) |
C6—C5—C8—N2 | −24.5 (6) | C18—C11—C21—C22 | −59.4 (4) |
C8—N2—C9—O1 | −2.2 (4) | C10—C11—C21—C22 | −177.3 (3) |
C8—N2—C9—C10 | 179.8 (3) | C23—N4—C22—O4 | −0.8 (4) |
N1—O1—C9—N2 | 1.3 (4) | C23—N4—C22—C21 | −179.5 (4) |
N1—O1—C9—C10 | 179.5 (3) | N3—O4—C22—N4 | 0.8 (5) |
N2—C9—C10—C11 | −85.5 (5) | N3—O4—C22—C21 | 179.6 (3) |
O1—C9—C10—C11 | 96.6 (4) | C11—C21—C22—N4 | 14.0 (6) |
C9—C10—C11—C12 | −37.6 (4) | C11—C21—C22—O4 | −164.6 (3) |
C9—C10—C11—C21 | −164.9 (3) | O4—N3—C23—N4 | −0.2 (5) |
C9—C10—C11—C18 | 76.7 (4) | O4—N3—C23—C24 | −177.1 (3) |
C21—C11—C12—C13 | 62.8 (4) | C22—N4—C23—N3 | 0.6 (4) |
C18—C11—C12—C13 | −178.7 (3) | C22—N4—C23—C24 | 177.5 (3) |
C10—C11—C12—C13 | −60.6 (5) | N3—C23—C24—C29 | 167.6 (4) |
C21—C11—C12—C17 | −117.3 (3) | N4—C23—C24—C29 | −9.1 (5) |
C18—C11—C12—C17 | 1.2 (3) | N3—C23—C24—C25 | −10.1 (6) |
C10—C11—C12—C17 | 119.3 (3) | N4—C23—C24—C25 | 173.2 (3) |
C17—C12—C13—C14 | 0.4 (5) | C29—C24—C25—C26 | −1.5 (6) |
C11—C12—C13—C14 | −179.7 (3) | C23—C24—C25—C26 | 176.2 (4) |
C12—C13—C14—C15 | −0.2 (6) | C24—C25—C26—C27 | 0.1 (7) |
C13—C14—C15—C16 | 0.0 (6) | C25—C26—C27—C28 | 1.6 (6) |
C14—C15—C16—C17 | −0.1 (5) | C25—C26—C27—C30 | 179.9 (4) |
C15—C16—C17—C12 | 0.3 (5) | C26—C27—C28—C29 | −1.8 (6) |
C15—C16—C17—N5 | 178.9 (3) | C30—C27—C28—C29 | 179.8 (4) |
C13—C12—C17—C16 | −0.5 (5) | C25—C24—C29—C28 | 1.3 (6) |
C11—C12—C17—C16 | 179.6 (3) | C23—C24—C29—C28 | −176.4 (4) |
C13—C12—C17—N5 | −179.3 (3) | C27—C28—C29—C24 | 0.4 (6) |
C11—C12—C17—N5 | 0.7 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···N1i | 0.93 | 2.62 | 3.387 (6) | 140 |
C10—H10A···O2ii | 0.97 | 2.46 | 3.411 (5) | 166 |
C16—H16A···O2 | 0.93 | 2.30 | 2.834 (5) | 116 |
C29—H29A···N4 | 0.93 | 2.62 | 2.935 (4) | 100 |
Symmetry codes: (i) x, y−1, z; (ii) x−1/2, y+1/2, z. |