Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806038207/hb2149sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806038207/hb2149Isup2.hkl |
CCDC reference: 624708
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.
C30H25N5O6 | Z = 2 |
Mr = 551.55 | F(000) = 576 |
Triclinic, P1 | Dx = 1.358 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.6300 (17) Å | Cell parameters from 25 reflections |
b = 11.866 (2) Å | θ = 9–13° |
c = 14.616 (3) Å | µ = 0.10 mm−1 |
α = 108.95 (3)° | T = 293 K |
β = 99.02 (3)° | Block, colourless |
γ = 101.17 (3)° | 0.30 × 0.20 × 0.10 mm |
V = 1349.3 (6) Å3 |
Enraf–Nonius CAD-4 diffractometer | 2900 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.017 |
Graphite monochromator | θmax = 26.0°, θmin = 1.5° |
ω/2θ scans | h = 0→10 |
Absorption correction: ψ scan (North et al., 1968) | k = −14→14 |
Tmin = 0.977, Tmax = 0.990 | l = −17→18 |
5644 measured reflections | 3 standard reflections every 200 reflections |
5289 independent reflections |
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)] = 0.090 | H-atom parameters constrained |
wR(F2) = 0.223 | w = 1/[σ2(Fo2) + (0.06P)2 + 2P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
5272 reflections | Δρmax = 0.44 e Å−3 |
365 parameters | Δρmin = −0.60 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.016 (2) |
Experimental. 1H NMR (CDCl3): δ 8.20–8.21 (m, 1H), 7.49–7.51 (m, 2H), 7.39–7.40 (m, 2H), 7.32–7.35 (m, 2H), 7.25–7.29 (m, 1H), 7.09–7.11 (m, 2H), 7.01–7.03 (m, 2H), 3.84 (s, 6H), 3.78–3.81 (s, 2H), 3.69–3.72 (s, 2H), 2.79 (s, 3H). |
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 | 0.0119 (5) | −0.3145 (4) | 0.4303 (3) | 0.1095 (14) | |
O2 | 0.5030 (6) | 0.2212 (3) | 0.4452 (3) | 0.1050 (13) | |
O3 | 0.5615 (5) | 0.3922 (3) | 0.3182 (3) | 0.1068 (14) | |
O4 | 0.0780 (6) | 0.3887 (4) | 0.2863 (3) | 0.1161 (15) | |
O5 | 0.1912 (5) | 0.6866 (3) | 0.0801 (3) | 0.0838 (11) | |
O6 | 0.4701 (4) | 0.1580 (3) | −0.0386 (3) | 0.0785 (10) | |
N1 | 0.4181 (7) | 0.1898 (4) | 0.5122 (4) | 0.1062 (17) | |
N2 | 0.3857 (5) | 0.0245 (3) | 0.3744 (3) | 0.0680 (11) | |
N3 | 0.2838 (4) | 0.3007 (3) | 0.2621 (3) | 0.0582 (9) | |
N4 | 0.4138 (4) | 0.3121 (3) | 0.0691 (3) | 0.0629 (10) | |
N5 | 0.3938 (5) | 0.2181 (3) | −0.0952 (3) | 0.0787 (12) | |
C1 | −0.1049 (9) | −0.3885 (6) | 0.4599 (5) | 0.132 (3) | |
H1B | −0.1394 | −0.4711 | 0.4114 | 0.197* | |
H1C | −0.1969 | −0.3546 | 0.4652 | 0.197* | |
H1D | −0.0573 | −0.3899 | 0.5234 | 0.197* | |
C2 | 0.0754 (6) | −0.1935 (5) | 0.4913 (4) | 0.0749 (14) | |
C3 | 0.0434 (7) | −0.1397 (6) | 0.5813 (4) | 0.0827 (16) | |
H3A | −0.0270 | −0.1858 | 0.6059 | 0.099* | |
C4 | 0.1167 (8) | −0.0159 (6) | 0.6361 (4) | 0.0946 (19) | |
H4B | 0.0970 | 0.0206 | 0.6983 | 0.114* | |
C5 | 0.2167 (8) | 0.0527 (5) | 0.6000 (4) | 0.0886 (17) | |
H5B | 0.2641 | 0.1359 | 0.6375 | 0.106* | |
C6 | 0.2492 (6) | 0.0003 (5) | 0.5080 (4) | 0.0671 (13) | |
C7 | 0.1776 (6) | −0.1243 (5) | 0.4542 (4) | 0.0717 (13) | |
H7A | 0.1986 | −0.1616 | 0.3925 | 0.086* | |
C8 | 0.3520 (6) | 0.0715 (4) | 0.4654 (4) | 0.0700 (13) | |
C9 | 0.4787 (6) | 0.1180 (4) | 0.3653 (4) | 0.0710 (14) | |
C10 | 0.5549 (6) | 0.1261 (4) | 0.2837 (4) | 0.0754 (15) | |
H10A | 0.5644 | 0.0449 | 0.2458 | 0.090* | |
H10B | 0.6639 | 0.1805 | 0.3119 | 0.090* | |
C11 | 0.4613 (5) | 0.1738 (4) | 0.2131 (4) | 0.0600 (12) | |
C12 | 0.4458 (5) | 0.3035 (4) | 0.2697 (4) | 0.0651 (12) | |
C13 | 0.3420 (9) | 0.5227 (5) | 0.3626 (5) | 0.121 (2) | |
H13A | 0.2865 | 0.5854 | 0.3854 | 0.182* | |
H13B | 0.4118 | 0.5455 | 0.3229 | 0.182* | |
H13C | 0.4059 | 0.5143 | 0.4188 | 0.182* | |
C14 | 0.2214 (7) | 0.4039 (5) | 0.3019 (4) | 0.0726 (14) | |
C15 | 0.1858 (5) | 0.1788 (4) | 0.2014 (3) | 0.0513 (10) | |
C16 | 0.0177 (5) | 0.1356 (4) | 0.1765 (3) | 0.049 | |
H16A | −0.0489 | 0.1875 | 0.1957 | 0.058* | |
C17 | −0.0438 (6) | 0.0129 (5) | 0.1224 (4) | 0.0775 (14) | |
H17A | −0.1562 | −0.0183 | 0.1031 | 0.093* | |
C18 | 0.0478 (6) | −0.0657 (4) | 0.0951 (4) | 0.0769 (14) | |
H18A | −0.0010 | −0.1495 | 0.0612 | 0.092* | |
C19 | 0.2209 (6) | −0.0203 (4) | 0.1184 (4) | 0.0715 (14) | |
H19A | 0.2862 | −0.0726 | 0.0973 | 0.086* | |
C20 | 0.2869 (5) | 0.1024 (3) | 0.1727 (3) | 0.0539 (10) | |
C21 | 0.5557 (6) | 0.1789 (4) | 0.1333 (4) | 0.0768 (15) | |
H21A | 0.6629 | 0.2348 | 0.1658 | 0.092* | |
H21B | 0.5700 | 0.0975 | 0.1009 | 0.092* | |
C22 | 0.4775 (5) | 0.2193 (4) | 0.0562 (4) | 0.0638 (12) | |
C23 | 0.3641 (5) | 0.3073 (4) | −0.0261 (4) | 0.0571 (11) | |
C24 | 0.2851 (5) | 0.3973 (4) | −0.0497 (3) | 0.0558 (11) | |
C25 | 0.2764 (5) | 0.4968 (4) | 0.0293 (3) | 0.0544 (10) | |
H25A | 0.3172 | 0.5051 | 0.0946 | 0.065* | |
C26 | 0.2048 (5) | 0.5848 (4) | 0.0086 (4) | 0.0602 (11) | |
C27 | 0.1433 (6) | 0.5705 (5) | −0.0869 (4) | 0.0717 (13) | |
H27A | 0.0943 | 0.6290 | −0.0993 | 0.086* | |
C28 | 0.1514 (7) | 0.4725 (6) | −0.1651 (4) | 0.0875 (16) | |
H28A | 0.1087 | 0.4645 | −0.2300 | 0.105* | |
C29 | 0.2246 (7) | 0.3841 (5) | −0.1467 (4) | 0.0790 (14) | |
H29A | 0.2324 | 0.3173 | −0.1993 | 0.095* | |
C30 | 0.2563 (8) | 0.7079 (5) | 0.1802 (4) | 0.0930 (18) | |
H30A | 0.2374 | 0.7827 | 0.2220 | 0.140* | |
H30B | 0.3711 | 0.7156 | 0.1907 | 0.140* | |
H30C | 0.2049 | 0.6400 | 0.1965 | 0.140* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.115 (3) | 0.087 (3) | 0.102 (3) | −0.002 (2) | 0.039 (3) | 0.013 (2) |
O2 | 0.137 (4) | 0.048 (2) | 0.106 (3) | 0.012 (2) | 0.006 (3) | 0.015 (2) |
O3 | 0.074 (2) | 0.053 (2) | 0.163 (4) | 0.0042 (19) | −0.004 (2) | 0.022 (2) |
O4 | 0.112 (3) | 0.085 (3) | 0.149 (4) | 0.066 (3) | 0.030 (3) | 0.018 (3) |
O5 | 0.117 (3) | 0.0515 (19) | 0.102 (3) | 0.045 (2) | 0.043 (2) | 0.0314 (19) |
O6 | 0.077 (2) | 0.0471 (17) | 0.121 (3) | 0.0306 (17) | 0.049 (2) | 0.0234 (19) |
N1 | 0.152 (5) | 0.054 (3) | 0.095 (4) | 0.025 (3) | 0.018 (3) | 0.012 (3) |
N2 | 0.062 (2) | 0.051 (2) | 0.085 (3) | 0.024 (2) | 0.010 (2) | 0.016 (2) |
N3 | 0.059 (2) | 0.0409 (19) | 0.080 (2) | 0.0260 (17) | 0.0170 (18) | 0.0215 (17) |
N4 | 0.062 (2) | 0.045 (2) | 0.097 (3) | 0.0299 (18) | 0.036 (2) | 0.030 (2) |
N5 | 0.087 (3) | 0.050 (2) | 0.104 (3) | 0.028 (2) | 0.041 (3) | 0.020 (2) |
C1 | 0.131 (6) | 0.110 (5) | 0.149 (7) | 0.002 (5) | 0.061 (5) | 0.045 (5) |
C2 | 0.069 (3) | 0.078 (4) | 0.073 (3) | 0.027 (3) | 0.014 (3) | 0.019 (3) |
C3 | 0.083 (4) | 0.102 (4) | 0.077 (4) | 0.049 (3) | 0.022 (3) | 0.035 (3) |
C4 | 0.126 (5) | 0.105 (5) | 0.072 (4) | 0.076 (4) | 0.031 (4) | 0.029 (4) |
C5 | 0.117 (5) | 0.074 (4) | 0.072 (4) | 0.053 (4) | 0.008 (3) | 0.015 (3) |
C6 | 0.068 (3) | 0.067 (3) | 0.064 (3) | 0.037 (3) | 0.003 (2) | 0.017 (2) |
C7 | 0.071 (3) | 0.066 (3) | 0.069 (3) | 0.027 (3) | 0.015 (3) | 0.009 (3) |
C8 | 0.070 (3) | 0.052 (3) | 0.075 (3) | 0.029 (2) | −0.005 (3) | 0.011 (3) |
C9 | 0.060 (3) | 0.052 (3) | 0.091 (4) | 0.026 (2) | −0.008 (3) | 0.019 (3) |
C10 | 0.048 (3) | 0.060 (3) | 0.122 (4) | 0.026 (2) | 0.007 (3) | 0.037 (3) |
C11 | 0.038 (2) | 0.039 (2) | 0.104 (4) | 0.0181 (18) | 0.014 (2) | 0.025 (2) |
C12 | 0.049 (3) | 0.040 (2) | 0.107 (4) | 0.018 (2) | 0.012 (2) | 0.027 (2) |
C13 | 0.152 (6) | 0.053 (3) | 0.132 (5) | 0.038 (4) | 0.014 (5) | 0.002 (3) |
C14 | 0.081 (4) | 0.073 (3) | 0.080 (3) | 0.049 (3) | 0.025 (3) | 0.031 (3) |
C15 | 0.040 (2) | 0.054 (2) | 0.071 (3) | 0.0201 (19) | 0.0169 (19) | 0.032 (2) |
C16 | 0.049 | 0.049 | 0.049 | 0.013 | 0.012 | 0.018 |
C17 | 0.048 (3) | 0.091 (4) | 0.093 (4) | 0.015 (3) | 0.015 (3) | 0.036 (3) |
C18 | 0.079 (4) | 0.046 (3) | 0.089 (4) | 0.003 (3) | 0.006 (3) | 0.016 (2) |
C19 | 0.079 (3) | 0.033 (2) | 0.092 (3) | 0.019 (2) | 0.004 (3) | 0.013 (2) |
C20 | 0.049 (2) | 0.039 (2) | 0.078 (3) | 0.0147 (18) | 0.013 (2) | 0.026 (2) |
C21 | 0.053 (3) | 0.054 (3) | 0.140 (5) | 0.028 (2) | 0.036 (3) | 0.041 (3) |
C22 | 0.050 (3) | 0.045 (2) | 0.106 (4) | 0.017 (2) | 0.039 (3) | 0.029 (3) |
C23 | 0.055 (3) | 0.040 (2) | 0.079 (3) | 0.0125 (19) | 0.032 (2) | 0.018 (2) |
C24 | 0.054 (3) | 0.039 (2) | 0.077 (3) | 0.0112 (19) | 0.027 (2) | 0.019 (2) |
C25 | 0.053 (3) | 0.043 (2) | 0.073 (3) | 0.0121 (19) | 0.023 (2) | 0.024 (2) |
C26 | 0.063 (3) | 0.049 (2) | 0.081 (3) | 0.019 (2) | 0.031 (2) | 0.032 (2) |
C27 | 0.069 (3) | 0.068 (3) | 0.098 (4) | 0.027 (3) | 0.030 (3) | 0.046 (3) |
C28 | 0.095 (4) | 0.099 (4) | 0.084 (4) | 0.031 (3) | 0.025 (3) | 0.049 (3) |
C29 | 0.090 (4) | 0.067 (3) | 0.078 (4) | 0.024 (3) | 0.027 (3) | 0.019 (3) |
C30 | 0.141 (5) | 0.055 (3) | 0.094 (4) | 0.045 (3) | 0.050 (4) | 0.021 (3) |
O1—C2 | 1.367 (6) | C10—H10B | 0.9700 |
O1—C1 | 1.420 (7) | C11—C20 | 1.495 (6) |
O2—C9 | 1.342 (6) | C11—C12 | 1.535 (5) |
O2—N1 | 1.412 (6) | C11—C21 | 1.533 (6) |
O3—C12 | 1.222 (5) | C13—C14 | 1.479 (8) |
O4—C14 | 1.190 (6) | C13—H13A | 0.9600 |
O5—C26 | 1.355 (5) | C13—H13B | 0.9600 |
O5—C30 | 1.403 (6) | C13—H13C | 0.9600 |
O6—C22 | 1.324 (5) | C15—C16 | 1.387 (5) |
O6—N5 | 1.423 (5) | C15—C20 | 1.391 (5) |
N1—C8 | 1.307 (6) | C16—C17 | 1.359 (6) |
N2—C9 | 1.295 (6) | C16—H16A | 0.9300 |
N2—C8 | 1.366 (6) | C17—C18 | 1.340 (7) |
N3—C12 | 1.378 (5) | C17—H17A | 0.9300 |
N3—C14 | 1.421 (5) | C18—C19 | 1.431 (7) |
N3—C15 | 1.432 (5) | C18—H18A | 0.9300 |
N4—C22 | 1.297 (5) | C19—C20 | 1.363 (5) |
N4—C23 | 1.370 (6) | C19—H19A | 0.9300 |
N5—C23 | 1.303 (5) | C21—C22 | 1.482 (7) |
C1—H1B | 0.9600 | C21—H21A | 0.9700 |
C1—H1C | 0.9600 | C21—H21B | 0.9700 |
C1—H1D | 0.9600 | C23—C24 | 1.472 (6) |
C2—C3 | 1.360 (7) | C24—C25 | 1.381 (5) |
C2—C7 | 1.380 (7) | C24—C29 | 1.378 (7) |
C3—C4 | 1.385 (8) | C25—C26 | 1.401 (6) |
C3—H3A | 0.9300 | C25—H25A | 0.9300 |
C4—C5 | 1.354 (8) | C26—C27 | 1.355 (6) |
C4—H4B | 0.9300 | C27—C28 | 1.363 (7) |
C5—C6 | 1.385 (7) | C27—H27A | 0.9300 |
C5—H5B | 0.9300 | C28—C29 | 1.400 (7) |
C6—C7 | 1.387 (6) | C28—H28A | 0.9300 |
C6—C8 | 1.454 (7) | C29—H29A | 0.9300 |
C7—H7A | 0.9300 | C30—H30A | 0.9600 |
C9—C10 | 1.470 (7) | C30—H30B | 0.9600 |
C10—C11 | 1.527 (6) | C30—H30C | 0.9600 |
C10—H10A | 0.9700 | ||
C2—O1—C1 | 117.5 (5) | H13A—C13—H13C | 109.5 |
C9—O2—N1 | 107.7 (4) | H13B—C13—H13C | 109.5 |
C26—O5—C30 | 118.9 (4) | O4—C14—N3 | 118.4 (5) |
C22—O6—N5 | 107.3 (3) | O4—C14—C13 | 124.8 (5) |
C8—N1—O2 | 102.6 (5) | N3—C14—C13 | 116.7 (5) |
C9—N2—C8 | 104.5 (4) | C16—C15—C20 | 122.5 (4) |
C12—N3—C14 | 125.7 (4) | C16—C15—N3 | 128.3 (4) |
C12—N3—C15 | 109.6 (3) | C20—C15—N3 | 109.0 (3) |
C14—N3—C15 | 124.6 (4) | C17—C16—C15 | 116.1 (4) |
C22—N4—C23 | 102.7 (4) | C17—C16—H16A | 121.9 |
C23—N5—O6 | 101.8 (4) | C15—C16—H16A | 121.9 |
O1—C1—H1B | 109.5 | C18—C17—C16 | 123.9 (5) |
O1—C1—H1C | 109.5 | C18—C17—H17A | 118.0 |
H1B—C1—H1C | 109.5 | C16—C17—H17A | 118.0 |
O1—C1—H1D | 109.5 | C17—C18—C19 | 119.8 (4) |
H1B—C1—H1D | 109.5 | C17—C18—H18A | 120.1 |
H1C—C1—H1D | 109.5 | C19—C18—H18A | 120.1 |
C3—C2—O1 | 125.3 (6) | C20—C19—C18 | 117.8 (4) |
C3—C2—C7 | 120.1 (5) | C20—C19—H19A | 121.1 |
O1—C2—C7 | 114.5 (5) | C18—C19—H19A | 121.1 |
C2—C3—C4 | 119.4 (6) | C19—C20—C15 | 119.8 (4) |
C2—C3—H3A | 120.3 | C19—C20—C11 | 129.8 (4) |
C4—C3—H3A | 120.3 | C15—C20—C11 | 110.4 (3) |
C5—C4—C3 | 120.8 (5) | C22—C21—C11 | 114.7 (3) |
C5—C4—H4B | 119.6 | C22—C21—H21A | 108.6 |
C3—C4—H4B | 119.6 | C11—C21—H21A | 108.6 |
C4—C5—C6 | 120.8 (6) | C22—C21—H21B | 108.6 |
C4—C5—H5B | 119.6 | C11—C21—H21B | 108.6 |
C6—C5—H5B | 119.6 | H21A—C21—H21B | 107.6 |
C7—C6—C5 | 118.2 (5) | N4—C22—O6 | 113.0 (4) |
C7—C6—C8 | 119.3 (4) | N4—C22—C21 | 127.8 (5) |
C5—C6—C8 | 122.4 (5) | O6—C22—C21 | 119.2 (4) |
C2—C7—C6 | 120.7 (5) | N5—C23—N4 | 115.3 (4) |
C2—C7—H7A | 119.7 | N5—C23—C24 | 121.8 (5) |
C6—C7—H7A | 119.7 | N4—C23—C24 | 122.9 (4) |
N1—C8—N2 | 114.0 (5) | C25—C24—C29 | 121.1 (4) |
N1—C8—C6 | 121.4 (5) | C25—C24—C23 | 117.4 (4) |
N2—C8—C6 | 124.6 (4) | C29—C24—C23 | 121.5 (4) |
N2—C9—O2 | 111.1 (5) | C24—C25—C26 | 118.4 (4) |
N2—C9—C10 | 130.4 (5) | C24—C25—H25A | 120.8 |
O2—C9—C10 | 118.5 (5) | C26—C25—H25A | 120.8 |
C9—C10—C11 | 113.7 (4) | O5—C26—C27 | 116.3 (4) |
C9—C10—H10A | 108.8 | O5—C26—C25 | 123.4 (4) |
C11—C10—H10A | 108.8 | C27—C26—C25 | 120.2 (4) |
C9—C10—H10B | 108.8 | C26—C27—C28 | 121.6 (5) |
C11—C10—H10B | 108.8 | C26—C27—H27A | 119.2 |
H10A—C10—H10B | 107.7 | C28—C27—H27A | 119.2 |
C20—C11—C10 | 112.8 (4) | C27—C28—C29 | 119.4 (5) |
C20—C11—C12 | 101.6 (3) | C27—C28—H28A | 120.3 |
C10—C11—C12 | 110.7 (4) | C29—C28—H28A | 120.3 |
C20—C11—C21 | 114.3 (4) | C24—C29—C28 | 119.2 (5) |
C10—C11—C21 | 107.8 (3) | C24—C29—H29A | 120.4 |
C12—C11—C21 | 109.5 (4) | C28—C29—H29A | 120.4 |
O3—C12—N3 | 126.4 (4) | O5—C30—H30A | 109.5 |
O3—C12—C11 | 124.1 (4) | O5—C30—H30B | 109.5 |
N3—C12—C11 | 109.4 (4) | H30A—C30—H30B | 109.5 |
C14—C13—H13A | 109.5 | O5—C30—H30C | 109.5 |
C14—C13—H13B | 109.5 | H30A—C30—H30C | 109.5 |
H13A—C13—H13B | 109.5 | H30B—C30—H30C | 109.5 |
C14—C13—H13C | 109.5 | ||
C9—O2—N1—C8 | −0.1 (6) | C14—N3—C15—C20 | 177.8 (4) |
C22—O6—N5—C23 | −0.6 (4) | C20—C15—C16—C17 | 0.4 (6) |
C1—O1—C2—C3 | 4.3 (8) | N3—C15—C16—C17 | −176.0 (4) |
C1—O1—C2—C7 | −174.8 (5) | C15—C16—C17—C18 | 1.7 (7) |
O1—C2—C3—C4 | 179.7 (5) | C16—C17—C18—C19 | −3.5 (8) |
C7—C2—C3—C4 | −1.2 (8) | C17—C18—C19—C20 | 3.2 (7) |
C2—C3—C4—C5 | 1.5 (8) | C18—C19—C20—C15 | −1.4 (7) |
C3—C4—C5—C6 | −0.6 (8) | C18—C19—C20—C11 | 175.8 (5) |
C4—C5—C6—C7 | −0.4 (7) | C16—C15—C20—C19 | −0.4 (7) |
C4—C5—C6—C8 | 178.1 (5) | N3—C15—C20—C19 | 176.6 (4) |
C3—C2—C7—C6 | 0.2 (7) | C16—C15—C20—C11 | −178.1 (4) |
O1—C2—C7—C6 | 179.4 (4) | N3—C15—C20—C11 | −1.1 (5) |
C5—C6—C7—C2 | 0.7 (7) | C10—C11—C20—C19 | −58.9 (7) |
C8—C6—C7—C2 | −178.0 (4) | C12—C11—C20—C19 | −177.4 (5) |
O2—N1—C8—N2 | −0.4 (6) | C21—C11—C20—C19 | 64.8 (6) |
O2—N1—C8—C6 | −179.1 (4) | C10—C11—C20—C15 | 118.5 (4) |
C9—N2—C8—N1 | 0.8 (5) | C12—C11—C20—C15 | −0.1 (5) |
C9—N2—C8—C6 | 179.4 (4) | C21—C11—C20—C15 | −117.8 (4) |
C7—C6—C8—N1 | 178.0 (5) | C20—C11—C21—C22 | 51.6 (5) |
C5—C6—C8—N1 | −0.5 (7) | C10—C11—C21—C22 | 177.9 (4) |
C7—C6—C8—N2 | −0.4 (7) | C12—C11—C21—C22 | −61.6 (5) |
C5—C6—C8—N2 | −179.0 (4) | C23—N4—C22—O6 | −0.4 (5) |
C8—N2—C9—O2 | −0.8 (5) | C23—N4—C22—C21 | 178.7 (4) |
C8—N2—C9—C10 | 180.0 (4) | N5—O6—C22—N4 | 0.7 (5) |
N1—O2—C9—N2 | 0.6 (6) | N5—O6—C22—C21 | −178.5 (4) |
N1—O2—C9—C10 | 179.9 (4) | C11—C21—C22—N4 | 46.0 (6) |
N2—C9—C10—C11 | 98.1 (6) | C11—C21—C22—O6 | −135.0 (4) |
O2—C9—C10—C11 | −81.0 (5) | O6—N5—C23—N4 | 0.5 (5) |
C9—C10—C11—C20 | −53.5 (5) | O6—N5—C23—C24 | 179.4 (4) |
C9—C10—C11—C12 | 59.5 (5) | C22—N4—C23—N5 | −0.1 (5) |
C9—C10—C11—C21 | 179.3 (4) | C22—N4—C23—C24 | −179.0 (4) |
C14—N3—C12—O3 | 6.3 (8) | N5—C23—C24—C25 | −172.4 (4) |
C15—N3—C12—O3 | −177.8 (5) | N4—C23—C24—C25 | 6.5 (6) |
C14—N3—C12—C11 | −177.8 (4) | N5—C23—C24—C29 | 6.5 (6) |
C15—N3—C12—C11 | −1.9 (5) | N4—C23—C24—C29 | −174.7 (4) |
C20—C11—C12—O3 | 177.2 (5) | C29—C24—C25—C26 | −0.2 (6) |
C10—C11—C12—O3 | 57.2 (6) | C23—C24—C25—C26 | 178.7 (4) |
C21—C11—C12—O3 | −61.5 (6) | C30—O5—C26—C27 | −178.4 (4) |
C20—C11—C12—N3 | 1.2 (5) | C30—O5—C26—C25 | 2.1 (7) |
C10—C11—C12—N3 | −118.8 (4) | C24—C25—C26—O5 | −179.4 (4) |
C21—C11—C12—N3 | 122.4 (4) | C24—C25—C26—C27 | 1.2 (6) |
C12—N3—C14—O4 | 177.1 (5) | O5—C26—C27—C28 | 179.3 (4) |
C15—N3—C14—O4 | 1.8 (7) | C25—C26—C27—C28 | −1.2 (7) |
C12—N3—C14—C13 | −4.4 (7) | C26—C27—C28—C29 | 0.2 (8) |
C15—N3—C14—C13 | −179.7 (5) | C25—C24—C29—C28 | −0.8 (7) |
C12—N3—C15—C16 | 178.6 (4) | C23—C24—C29—C28 | −179.7 (4) |
C14—N3—C15—C16 | −5.4 (7) | C27—C28—C29—C24 | 0.9 (8) |
C12—N3—C15—C20 | 1.9 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7A···N2 | 0.93 | 2.59 | 2.910 (7) | 101 |
C16—H16A···O4 | 0.93 | 2.27 | 2.805 (7) | 116 |
C25—H25A···N4 | 0.93 | 2.52 | 2.858 (6) | 102 |