Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007063/ci6539sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007063/ci6539Isup2.hkl |
CCDC reference: 270268
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.
C32H32N4O | F(000) = 1040 |
Mr = 488.62 | Dx = 1.248 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1853 reflections |
a = 15.359 (3) Å | θ = 2.7–22.1° |
b = 13.215 (3) Å | µ = 0.08 mm−1 |
c = 12.969 (3) Å | T = 273 K |
β = 99.051 (3)° | Block, colourless |
V = 2599.5 (9) Å3 | 0.34 × 0.24 × 0.16 mm |
Z = 4 |
Bruker APEX CCD area-detector diffractometer | 4581 independent reflections |
Radiation source: fine-focus sealed tube | 3018 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→18 |
Tmin = 0.974, Tmax = 0.988 | k = −15→12 |
13748 measured 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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0608P)2 + 0.1682P] where P = (Fo2 + 2Fc2)/3 |
4581 reflections | (Δ/σ)max = 0.001 |
337 parameters | Δρmax = 0.17 e Å−3 |
0 restraints | Δρmin = −0.16 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 | ||
O1 | 0.06646 (8) | 0.21331 (8) | 0.55741 (10) | 0.0476 (3) | |
N1 | −0.04345 (10) | 0.14646 (11) | 0.64094 (12) | 0.0465 (4) | |
N2 | 0.09886 (11) | 0.35749 (11) | 0.71722 (12) | 0.0494 (4) | |
N3 | 0.31739 (10) | 0.32099 (11) | 0.40858 (12) | 0.0454 (4) | |
N4 | 0.40412 (11) | 0.29443 (13) | 0.23157 (13) | 0.0553 (4) | |
C1 | 0.01382 (14) | 0.07141 (15) | 0.69900 (17) | 0.0583 (6) | |
H1A | −0.0213 | 0.0229 | 0.7292 | 0.088* | |
H1B | 0.0533 | 0.1043 | 0.7535 | 0.088* | |
H1C | 0.0472 | 0.0375 | 0.6527 | 0.088* | |
C2 | −0.10592 (12) | 0.11614 (13) | 0.55568 (15) | 0.0442 (5) | |
C3 | −0.14256 (13) | 0.02173 (14) | 0.53366 (17) | 0.0545 (5) | |
H3 | −0.1260 | −0.0332 | 0.5772 | 0.065* | |
C4 | −0.20457 (15) | 0.01151 (16) | 0.44503 (18) | 0.0646 (6) | |
H4 | −0.2304 | −0.0514 | 0.4291 | 0.078* | |
C5 | −0.22913 (15) | 0.09199 (16) | 0.37966 (18) | 0.0664 (6) | |
H5 | −0.2709 | 0.0830 | 0.3202 | 0.080* | |
C6 | −0.19169 (14) | 0.18669 (15) | 0.40240 (17) | 0.0587 (5) | |
H6 | −0.2080 | 0.2414 | 0.3585 | 0.070* | |
C7 | −0.13033 (12) | 0.19842 (13) | 0.49044 (15) | 0.0463 (5) | |
C8 | −0.08182 (13) | 0.29121 (13) | 0.53673 (15) | 0.0501 (5) | |
C9 | −0.14298 (15) | 0.35095 (17) | 0.5980 (2) | 0.0773 (7) | |
H9A | −0.1950 | 0.3712 | 0.5515 | 0.116* | |
H9B | −0.1127 | 0.4099 | 0.6284 | 0.116* | |
H9C | −0.1594 | 0.3090 | 0.6522 | 0.116* | |
C10 | −0.04911 (15) | 0.35960 (16) | 0.45660 (18) | 0.0709 (7) | |
H10A | −0.0111 | 0.3218 | 0.4187 | 0.106* | |
H10B | −0.0170 | 0.4154 | 0.4916 | 0.106* | |
H10C | −0.0985 | 0.3848 | 0.4089 | 0.106* | |
C11 | −0.00567 (12) | 0.24029 (13) | 0.61384 (15) | 0.0451 (5) | |
C12 | 0.03011 (13) | 0.30241 (14) | 0.70723 (15) | 0.0506 (5) | |
H12 | −0.0008 | 0.3006 | 0.7634 | 0.061* | |
C13 | 0.14920 (12) | 0.35371 (13) | 0.63516 (14) | 0.0424 (4) | |
C14 | 0.22010 (12) | 0.42289 (13) | 0.63433 (14) | 0.0425 (4) | |
C15 | 0.23794 (13) | 0.50184 (14) | 0.70834 (15) | 0.0515 (5) | |
H15 | 0.2024 | 0.5094 | 0.7596 | 0.062* | |
C16 | 0.30583 (14) | 0.56642 (15) | 0.70571 (17) | 0.0602 (6) | |
H16 | 0.3153 | 0.6191 | 0.7537 | 0.072* | |
C17 | 0.36184 (14) | 0.55470 (15) | 0.63157 (18) | 0.0629 (6) | |
H17 | 0.4087 | 0.5992 | 0.6309 | 0.075* | |
C18 | 0.34818 (13) | 0.47862 (14) | 0.56035 (17) | 0.0539 (5) | |
H18 | 0.3868 | 0.4706 | 0.5125 | 0.065* | |
C19 | 0.27638 (11) | 0.41176 (12) | 0.55781 (14) | 0.0429 (4) | |
C20 | 0.25923 (12) | 0.33148 (13) | 0.48254 (14) | 0.0426 (4) | |
C21 | 0.18994 (12) | 0.26750 (13) | 0.48520 (14) | 0.0444 (5) | |
H21 | 0.1791 | 0.2155 | 0.4366 | 0.053* | |
C22 | 0.13506 (12) | 0.27981 (12) | 0.56074 (14) | 0.0421 (4) | |
C23 | 0.30280 (13) | 0.39263 (15) | 0.32228 (16) | 0.0567 (5) | |
H23A | 0.2927 | 0.4596 | 0.3485 | 0.068* | |
H23B | 0.2510 | 0.3730 | 0.2736 | 0.068* | |
C24 | 0.38218 (14) | 0.39448 (16) | 0.26702 (18) | 0.0629 (6) | |
H24A | 0.3706 | 0.4395 | 0.2074 | 0.075* | |
H24B | 0.4323 | 0.4211 | 0.3141 | 0.075* | |
C25 | 0.40577 (15) | 0.21672 (15) | 0.31143 (18) | 0.0606 (6) | |
H25A | 0.4585 | 0.2251 | 0.3628 | 0.073* | |
H25B | 0.4087 | 0.1507 | 0.2795 | 0.073* | |
C26 | 0.32584 (14) | 0.22075 (14) | 0.36581 (17) | 0.0587 (6) | |
H26A | 0.2734 | 0.2047 | 0.3166 | 0.070* | |
H26B | 0.3317 | 0.1711 | 0.4215 | 0.070* | |
C27 | 0.47279 (14) | 0.29090 (16) | 0.17116 (16) | 0.0560 (5) | |
C28 | 0.49206 (16) | 0.37211 (19) | 0.11144 (18) | 0.0751 (7) | |
H28 | 0.4593 | 0.4313 | 0.1116 | 0.090* | |
C29 | 0.55888 (17) | 0.3676 (2) | 0.05138 (19) | 0.0851 (8) | |
H29 | 0.5701 | 0.4237 | 0.0121 | 0.102* | |
C30 | 0.60812 (17) | 0.2832 (2) | 0.0487 (2) | 0.0835 (8) | |
H30 | 0.6527 | 0.2804 | 0.0079 | 0.100* | |
C31 | 0.5909 (2) | 0.2031 (2) | 0.1069 (2) | 0.0931 (9) | |
H31 | 0.6243 | 0.1445 | 0.1059 | 0.112* | |
C32 | 0.52491 (17) | 0.20604 (19) | 0.1676 (2) | 0.0816 (8) | |
H32 | 0.5152 | 0.1496 | 0.2071 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0524 (8) | 0.0400 (7) | 0.0543 (8) | −0.0099 (6) | 0.0202 (7) | −0.0088 (6) |
N1 | 0.0516 (10) | 0.0400 (9) | 0.0498 (10) | −0.0037 (7) | 0.0139 (8) | 0.0035 (7) |
N2 | 0.0570 (10) | 0.0473 (9) | 0.0452 (10) | −0.0016 (8) | 0.0119 (8) | −0.0056 (7) |
N3 | 0.0492 (9) | 0.0414 (9) | 0.0471 (9) | −0.0010 (7) | 0.0124 (8) | 0.0002 (7) |
N4 | 0.0528 (10) | 0.0644 (11) | 0.0517 (10) | 0.0029 (8) | 0.0168 (9) | −0.0004 (8) |
C1 | 0.0645 (13) | 0.0495 (12) | 0.0614 (14) | 0.0001 (10) | 0.0111 (11) | 0.0109 (10) |
C2 | 0.0476 (11) | 0.0436 (11) | 0.0455 (11) | −0.0043 (8) | 0.0194 (9) | −0.0012 (8) |
C3 | 0.0665 (14) | 0.0425 (11) | 0.0575 (13) | −0.0069 (10) | 0.0193 (11) | 0.0004 (9) |
C4 | 0.0784 (16) | 0.0494 (13) | 0.0666 (15) | −0.0150 (11) | 0.0129 (13) | −0.0095 (11) |
C5 | 0.0680 (15) | 0.0637 (14) | 0.0644 (15) | −0.0089 (11) | 0.0011 (12) | −0.0066 (11) |
C6 | 0.0634 (14) | 0.0511 (12) | 0.0603 (14) | 0.0020 (10) | 0.0062 (12) | 0.0043 (10) |
C7 | 0.0481 (11) | 0.0407 (10) | 0.0521 (12) | −0.0009 (8) | 0.0139 (10) | −0.0010 (9) |
C8 | 0.0555 (12) | 0.0388 (10) | 0.0564 (12) | −0.0009 (8) | 0.0098 (10) | 0.0019 (9) |
C9 | 0.0734 (16) | 0.0621 (14) | 0.0951 (19) | 0.0139 (11) | 0.0090 (14) | −0.0224 (13) |
C10 | 0.0809 (16) | 0.0494 (12) | 0.0784 (16) | −0.0103 (11) | −0.0002 (13) | 0.0179 (11) |
C11 | 0.0493 (11) | 0.0392 (10) | 0.0504 (11) | −0.0025 (8) | 0.0186 (9) | −0.0015 (8) |
C12 | 0.0567 (13) | 0.0501 (11) | 0.0479 (12) | −0.0036 (9) | 0.0165 (10) | −0.0045 (9) |
C13 | 0.0475 (11) | 0.0408 (10) | 0.0391 (10) | −0.0011 (8) | 0.0078 (9) | −0.0009 (8) |
C14 | 0.0470 (11) | 0.0371 (10) | 0.0412 (10) | 0.0028 (8) | 0.0001 (9) | −0.0005 (8) |
C15 | 0.0573 (12) | 0.0456 (11) | 0.0491 (12) | −0.0013 (9) | 0.0008 (10) | −0.0061 (9) |
C16 | 0.0654 (14) | 0.0487 (12) | 0.0622 (14) | −0.0070 (10) | −0.0034 (12) | −0.0123 (10) |
C17 | 0.0568 (13) | 0.0510 (13) | 0.0774 (16) | −0.0158 (10) | 0.0000 (12) | −0.0060 (11) |
C18 | 0.0495 (12) | 0.0506 (12) | 0.0610 (13) | −0.0077 (9) | 0.0065 (10) | −0.0020 (10) |
C19 | 0.0431 (10) | 0.0373 (10) | 0.0462 (11) | −0.0013 (8) | 0.0007 (9) | 0.0020 (8) |
C20 | 0.0450 (11) | 0.0403 (10) | 0.0428 (11) | 0.0008 (8) | 0.0081 (9) | 0.0023 (8) |
C21 | 0.0506 (11) | 0.0391 (10) | 0.0449 (11) | −0.0043 (8) | 0.0118 (9) | −0.0056 (8) |
C22 | 0.0463 (11) | 0.0350 (10) | 0.0452 (11) | −0.0035 (8) | 0.0078 (9) | −0.0008 (8) |
C23 | 0.0523 (12) | 0.0620 (13) | 0.0581 (13) | 0.0121 (10) | 0.0155 (10) | 0.0142 (10) |
C24 | 0.0616 (13) | 0.0615 (14) | 0.0703 (15) | 0.0143 (10) | 0.0251 (12) | 0.0191 (11) |
C25 | 0.0670 (14) | 0.0498 (12) | 0.0694 (14) | 0.0026 (10) | 0.0247 (12) | −0.0006 (10) |
C26 | 0.0680 (14) | 0.0500 (12) | 0.0625 (14) | −0.0052 (10) | 0.0243 (12) | −0.0049 (10) |
C27 | 0.0505 (12) | 0.0716 (14) | 0.0465 (12) | −0.0002 (10) | 0.0087 (10) | −0.0076 (10) |
C28 | 0.0762 (16) | 0.0894 (17) | 0.0657 (15) | 0.0170 (13) | 0.0293 (13) | 0.0169 (13) |
C29 | 0.0867 (19) | 0.111 (2) | 0.0651 (17) | 0.0075 (16) | 0.0345 (15) | 0.0166 (14) |
C30 | 0.0735 (17) | 0.119 (2) | 0.0643 (16) | 0.0005 (16) | 0.0318 (14) | −0.0161 (15) |
C31 | 0.099 (2) | 0.091 (2) | 0.101 (2) | 0.0098 (16) | 0.0507 (19) | −0.0126 (17) |
C32 | 0.0860 (18) | 0.0729 (16) | 0.0969 (19) | 0.0046 (13) | 0.0485 (16) | −0.0058 (14) |
O1—C22 | 1.367 (2) | C13—C22 | 1.366 (2) |
O1—C11 | 1.465 (2) | C13—C14 | 1.423 (2) |
N1—C2 | 1.404 (2) | C14—C15 | 1.415 (2) |
N1—C11 | 1.436 (2) | C14—C19 | 1.423 (2) |
N1—C1 | 1.455 (2) | C15—C16 | 1.352 (3) |
N2—C12 | 1.272 (2) | C15—H15 | 0.93 |
N2—C13 | 1.411 (2) | C16—C17 | 1.396 (3) |
N3—C20 | 1.417 (2) | C16—H16 | 0.93 |
N3—C26 | 1.450 (2) | C17—C18 | 1.359 (3) |
N3—C23 | 1.456 (2) | C17—H17 | 0.93 |
N4—C27 | 1.410 (2) | C18—C19 | 1.410 (3) |
N4—C25 | 1.456 (3) | C18—H18 | 0.93 |
N4—C24 | 1.457 (3) | C19—C20 | 1.438 (2) |
C1—H1A | 0.96 | C20—C21 | 1.364 (2) |
C1—H1B | 0.96 | C21—C22 | 1.399 (2) |
C1—H1C | 0.96 | C21—H21 | 0.93 |
C2—C3 | 1.380 (3) | C23—C24 | 1.509 (3) |
C2—C7 | 1.392 (3) | C23—H23A | 0.97 |
C3—C4 | 1.379 (3) | C23—H23B | 0.97 |
C3—H3 | 0.93 | C24—H24A | 0.97 |
C4—C5 | 1.375 (3) | C24—H24B | 0.97 |
C4—H4 | 0.93 | C25—C26 | 1.510 (3) |
C5—C6 | 1.389 (3) | C25—H25A | 0.97 |
C5—H5 | 0.93 | C25—H25B | 0.97 |
C6—C7 | 1.370 (3) | C26—H26A | 0.97 |
C6—H6 | 0.93 | C26—H26B | 0.97 |
C7—C8 | 1.509 (3) | C27—C28 | 1.383 (3) |
C8—C10 | 1.521 (3) | C27—C32 | 1.383 (3) |
C8—C9 | 1.540 (3) | C28—C29 | 1.384 (3) |
C8—C11 | 1.566 (3) | C28—H28 | 0.93 |
C9—H9A | 0.96 | C29—C30 | 1.351 (4) |
C9—H9B | 0.96 | C29—H29 | 0.93 |
C9—H9C | 0.96 | C30—C31 | 1.350 (4) |
C10—H10A | 0.96 | C30—H30 | 0.93 |
C10—H10B | 0.96 | C31—C32 | 1.378 (3) |
C10—H10C | 0.96 | C31—H31 | 0.93 |
C11—C12 | 1.494 (3) | C32—H32 | 0.93 |
C12—H12 | 0.93 | ||
C22—O1—C11 | 117.87 (13) | C19—C14—C13 | 119.24 (16) |
C2—N1—C11 | 107.83 (14) | C16—C15—C14 | 121.07 (19) |
C2—N1—C1 | 119.73 (15) | C16—C15—H15 | 119.5 |
C11—N1—C1 | 118.73 (15) | C14—C15—H15 | 119.5 |
C12—N2—C13 | 116.58 (16) | C15—C16—C17 | 120.58 (19) |
C20—N3—C26 | 116.89 (14) | C15—C16—H16 | 119.7 |
C20—N3—C23 | 114.81 (14) | C17—C16—H16 | 119.7 |
C26—N3—C23 | 108.20 (15) | C18—C17—C16 | 120.28 (19) |
C27—N4—C25 | 116.17 (16) | C18—C17—H17 | 119.9 |
C27—N4—C24 | 115.84 (16) | C16—C17—H17 | 119.9 |
C25—N4—C24 | 113.25 (16) | C17—C18—C19 | 121.08 (19) |
N1—C1—H1A | 109.5 | C17—C18—H18 | 119.5 |
N1—C1—H1B | 109.5 | C19—C18—H18 | 119.5 |
H1A—C1—H1B | 109.5 | C18—C19—C14 | 118.55 (17) |
N1—C1—H1C | 109.5 | C18—C19—C20 | 122.52 (17) |
H1A—C1—H1C | 109.5 | C14—C19—C20 | 118.91 (15) |
H1B—C1—H1C | 109.5 | C21—C20—N3 | 122.28 (16) |
C3—C2—C7 | 121.21 (19) | C21—C20—C19 | 120.05 (16) |
C3—C2—N1 | 128.84 (18) | N3—C20—C19 | 117.66 (15) |
C7—C2—N1 | 109.95 (16) | C20—C21—C22 | 120.28 (16) |
C4—C3—C2 | 117.82 (19) | C20—C21—H21 | 119.9 |
C4—C3—H3 | 121.1 | C22—C21—H21 | 119.9 |
C2—C3—H3 | 121.1 | C13—C22—O1 | 121.18 (16) |
C5—C4—C3 | 121.6 (2) | C13—C22—C21 | 122.11 (16) |
C5—C4—H4 | 119.2 | O1—C22—C21 | 116.70 (15) |
C3—C4—H4 | 119.2 | N3—C23—C24 | 109.72 (15) |
C4—C5—C6 | 120.1 (2) | N3—C23—H23A | 109.7 |
C4—C5—H5 | 120.0 | C24—C23—H23A | 109.7 |
C6—C5—H5 | 120.0 | N3—C23—H23B | 109.7 |
C7—C6—C5 | 119.09 (19) | C24—C23—H23B | 109.7 |
C7—C6—H6 | 120.5 | H23A—C23—H23B | 108.2 |
C5—C6—H6 | 120.5 | N4—C24—C23 | 112.30 (17) |
C6—C7—C2 | 120.15 (17) | N4—C24—H24A | 109.1 |
C6—C7—C8 | 130.93 (17) | C23—C24—H24A | 109.1 |
C2—C7—C8 | 108.89 (17) | N4—C24—H24B | 109.1 |
C7—C8—C10 | 113.98 (17) | C23—C24—H24B | 109.1 |
C7—C8—C9 | 108.58 (16) | H24A—C24—H24B | 107.9 |
C10—C8—C9 | 109.97 (18) | N4—C25—C26 | 112.51 (17) |
C7—C8—C11 | 100.21 (14) | N4—C25—H25A | 109.1 |
C10—C8—C11 | 113.44 (16) | C26—C25—H25A | 109.1 |
C9—C8—C11 | 110.23 (16) | N4—C25—H25B | 109.1 |
C8—C9—H9A | 109.5 | C26—C25—H25B | 109.1 |
C8—C9—H9B | 109.5 | H25A—C25—H25B | 107.8 |
H9A—C9—H9B | 109.5 | N3—C26—C25 | 109.82 (15) |
C8—C9—H9C | 109.5 | N3—C26—H26A | 109.7 |
H9A—C9—H9C | 109.5 | C25—C26—H26A | 109.7 |
H9B—C9—H9C | 109.5 | N3—C26—H26B | 109.7 |
C8—C10—H10A | 109.5 | C25—C26—H26B | 109.7 |
C8—C10—H10B | 109.5 | H26A—C26—H26B | 108.2 |
H10A—C10—H10B | 109.5 | C28—C27—C32 | 115.7 (2) |
C8—C10—H10C | 109.5 | C28—C27—N4 | 122.03 (19) |
H10A—C10—H10C | 109.5 | C32—C27—N4 | 122.22 (19) |
H10B—C10—H10C | 109.5 | C27—C28—C29 | 121.7 (2) |
N1—C11—O1 | 106.18 (13) | C27—C28—H28 | 119.2 |
N1—C11—C12 | 112.78 (15) | C29—C28—H28 | 119.2 |
O1—C11—C12 | 109.15 (15) | C30—C29—C28 | 121.2 (2) |
N1—C11—C8 | 103.73 (14) | C30—C29—H29 | 119.4 |
O1—C11—C8 | 109.46 (14) | C28—C29—H29 | 119.4 |
C12—C11—C8 | 115.08 (15) | C31—C30—C29 | 118.2 (2) |
N2—C12—C11 | 126.17 (17) | C31—C30—H30 | 120.9 |
N2—C12—H12 | 116.9 | C29—C30—H30 | 120.9 |
C11—C12—H12 | 116.9 | C30—C31—C32 | 121.6 (3) |
C22—C13—N2 | 120.86 (16) | C30—C31—H31 | 119.2 |
C22—C13—C14 | 119.38 (16) | C32—C31—H31 | 119.2 |
N2—C13—C14 | 119.58 (16) | C31—C32—C27 | 121.6 (2) |
C15—C14—C19 | 118.38 (17) | C31—C32—H32 | 119.2 |
C15—C14—C13 | 122.37 (17) | C27—C32—H32 | 119.2 |
C11—N1—C2—C3 | 162.05 (18) | C19—C14—C15—C16 | 1.1 (3) |
C1—N1—C2—C3 | 22.1 (3) | C13—C14—C15—C16 | 179.94 (18) |
C11—N1—C2—C7 | −18.84 (19) | C14—C15—C16—C17 | −2.0 (3) |
C1—N1—C2—C7 | −158.77 (16) | C15—C16—C17—C18 | 0.6 (3) |
C7—C2—C3—C4 | −0.3 (3) | C16—C17—C18—C19 | 1.7 (3) |
N1—C2—C3—C4 | 178.74 (17) | C17—C18—C19—C14 | −2.5 (3) |
C2—C3—C4—C5 | 0.5 (3) | C17—C18—C19—C20 | 179.02 (19) |
C3—C4—C5—C6 | −0.4 (3) | C15—C14—C19—C18 | 1.1 (3) |
C4—C5—C6—C7 | 0.0 (3) | C13—C14—C19—C18 | −177.76 (17) |
C5—C6—C7—C2 | 0.2 (3) | C15—C14—C19—C20 | 179.66 (17) |
C5—C6—C7—C8 | −177.37 (19) | C13—C14—C19—C20 | 0.8 (3) |
C3—C2—C7—C6 | −0.1 (3) | C26—N3—C20—C21 | −25.4 (3) |
N1—C2—C7—C6 | −179.27 (16) | C23—N3—C20—C21 | 103.0 (2) |
C3—C2—C7—C8 | 178.00 (16) | C26—N3—C20—C19 | 153.37 (17) |
N1—C2—C7—C8 | −1.2 (2) | C23—N3—C20—C19 | −78.3 (2) |
C6—C7—C8—C10 | −42.3 (3) | C18—C19—C20—C21 | 178.48 (18) |
C2—C7—C8—C10 | 139.90 (18) | C14—C19—C20—C21 | 0.0 (3) |
C6—C7—C8—C9 | 80.7 (3) | C18—C19—C20—N3 | −0.3 (3) |
C2—C7—C8—C9 | −97.15 (19) | C14—C19—C20—N3 | −178.78 (15) |
C6—C7—C8—C11 | −163.80 (19) | N3—C20—C21—C22 | 178.97 (16) |
C2—C7—C8—C11 | 18.40 (18) | C19—C20—C21—C22 | 0.3 (3) |
C2—N1—C11—O1 | −85.53 (16) | N2—C13—C22—O1 | 6.4 (3) |
C1—N1—C11—O1 | 54.9 (2) | C14—C13—C22—O1 | −178.50 (16) |
C2—N1—C11—C12 | 154.98 (15) | N2—C13—C22—C21 | −172.95 (16) |
C1—N1—C11—C12 | −64.6 (2) | C14—C13—C22—C21 | 2.2 (3) |
C2—N1—C11—C8 | 29.81 (17) | C11—O1—C22—C13 | 17.7 (2) |
C1—N1—C11—C8 | 170.21 (15) | C11—O1—C22—C21 | −162.88 (15) |
C22—O1—C11—N1 | −152.93 (15) | C20—C21—C22—C13 | −1.4 (3) |
C22—O1—C11—C12 | −31.1 (2) | C20—C21—C22—O1 | 179.26 (16) |
C22—O1—C11—C8 | 95.69 (17) | C20—N3—C23—C24 | 163.99 (16) |
C7—C8—C11—N1 | −28.59 (16) | C26—N3—C23—C24 | −63.4 (2) |
C10—C8—C11—N1 | −150.48 (16) | C27—N4—C24—C23 | 174.65 (17) |
C9—C8—C11—N1 | 85.70 (18) | C25—N4—C24—C23 | −47.5 (2) |
C7—C8—C11—O1 | 84.40 (15) | N3—C23—C24—N4 | 55.7 (2) |
C10—C8—C11—O1 | −37.5 (2) | C27—N4—C25—C26 | −175.04 (17) |
C9—C8—C11—O1 | −161.31 (15) | C24—N4—C25—C26 | 47.3 (2) |
C7—C8—C11—C12 | −152.27 (15) | C20—N3—C26—C25 | −165.41 (17) |
C10—C8—C11—C12 | 85.8 (2) | C23—N3—C26—C25 | 63.1 (2) |
C9—C8—C11—C12 | −38.0 (2) | N4—C25—C26—N3 | −55.3 (2) |
C13—N2—C12—C11 | −4.8 (3) | C25—N4—C27—C28 | −163.9 (2) |
N1—C11—C12—N2 | 143.92 (19) | C24—N4—C27—C28 | −27.3 (3) |
O1—C11—C12—N2 | 26.2 (3) | C25—N4—C27—C32 | 16.4 (3) |
C8—C11—C12—N2 | −97.3 (2) | C24—N4—C27—C32 | 153.0 (2) |
C12—N2—C13—C22 | −13.2 (3) | C32—C27—C28—C29 | 0.6 (4) |
C12—N2—C13—C14 | 171.74 (17) | N4—C27—C28—C29 | −179.2 (2) |
C22—C13—C14—C15 | 179.33 (17) | C27—C28—C29—C30 | 0.0 (4) |
N2—C13—C14—C15 | −5.5 (3) | C30—C31—C32—C27 | 0.5 (4) |
C22—C13—C14—C19 | −1.8 (3) | C28—C27—C32—C31 | −0.9 (4) |
N2—C13—C14—C19 | 173.32 (16) | N4—C27—C32—C31 | 178.9 (2) |