Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805003132/ww6350sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805003132/ww6350Isup2.hkl |
CCDC reference: 269887
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL.
[Co(C13H18NO)2] | F(000) = 996 |
Mr = 467.50 | Dx = 1.188 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.122 (2) Å | Cell parameters from 3300 reflections |
b = 12.943 (2) Å | θ = 2.3–24.2° |
c = 15.893 (3) Å | µ = 0.68 mm−1 |
β = 104.517 (3)° | T = 293 K |
V = 2613.1 (8) Å3 | Block, red |
Z = 4 | 0.28 × 0.18 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 4615 independent reflections |
Radiation source: fine-focus sealed tube | 3070 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.044 |
φ and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −15→15 |
Tmin = 0.821, Tmax = 0.934 | k = −12→15 |
13408 measured reflections | l = −18→14 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.142 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0764P)2] where P = (Fo2 + 2Fc2)/3 |
4615 reflections | (Δ/σ)max = 0.003 |
290 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.40 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 | ||
Co1 | 0.74524 (4) | 0.30020 (4) | 0.22372 (2) | 0.04365 (18) | |
O1 | 0.7296 (2) | 0.22456 (16) | 0.11864 (13) | 0.0502 (6) | |
O2 | 0.69756 (17) | 0.25210 (18) | 0.32005 (12) | 0.0439 (6) | |
N1 | 0.6847 (2) | 0.4288 (2) | 0.16502 (16) | 0.0471 (7) | |
N2 | 0.8939 (2) | 0.3101 (2) | 0.28795 (18) | 0.0524 (8) | |
C1 | 0.7179 (2) | 0.2629 (3) | 0.03980 (18) | 0.0387 (8) | |
C2 | 0.7333 (3) | 0.1970 (2) | −0.02794 (19) | 0.0394 (8) | |
C3 | 0.7241 (3) | 0.2404 (3) | −0.1090 (2) | 0.0471 (9) | |
H3 | 0.7357 | 0.1980 | −0.1529 | 0.057* | |
C4 | 0.6989 (3) | 0.3431 (3) | −0.12902 (19) | 0.0542 (9) | |
C5 | 0.6802 (3) | 0.4054 (3) | −0.0648 (2) | 0.0524 (9) | |
H5 | 0.6604 | 0.4738 | −0.0775 | 0.063* | |
C6 | 0.6905 (3) | 0.3676 (2) | 0.02051 (19) | 0.0419 (8) | |
C7 | 0.6703 (3) | 0.4413 (3) | 0.0826 (2) | 0.0498 (9) | |
H7 | 0.6438 | 0.5051 | 0.0605 | 0.060* | |
C8 | 0.6585 (4) | 0.5165 (3) | 0.2150 (2) | 0.0790 (14) | |
H8A | 0.7219 | 0.5434 | 0.2526 | 0.119* | |
H8B | 0.6121 | 0.4935 | 0.2492 | 0.119* | |
H8C | 0.6246 | 0.5696 | 0.1757 | 0.119* | |
C9 | 0.7587 (3) | 0.0830 (3) | −0.0097 (2) | 0.0570 (10) | |
C10 | 0.8641 (4) | 0.0717 (3) | 0.0592 (2) | 0.0787 (13) | |
H10A | 0.8604 | 0.1080 | 0.1110 | 0.118* | |
H10B | 0.9198 | 0.1001 | 0.0372 | 0.118* | |
H10C | 0.8779 | −0.0001 | 0.0724 | 0.118* | |
C11 | 0.6694 (4) | 0.0300 (3) | 0.0214 (3) | 0.0863 (15) | |
H11A | 0.6051 | 0.0339 | −0.0236 | 0.129* | |
H11B | 0.6602 | 0.0643 | 0.0726 | 0.129* | |
H11C | 0.6872 | −0.0411 | 0.0346 | 0.129* | |
C12 | 0.7714 (5) | 0.0240 (3) | −0.0911 (3) | 0.0951 (17) | |
H12A | 0.7911 | −0.0463 | −0.0757 | 0.143* | |
H12B | 0.8250 | 0.0565 | −0.1133 | 0.143* | |
H12C | 0.7059 | 0.0250 | −0.1348 | 0.143* | |
C13 | 0.6909 (4) | 0.3848 (4) | −0.2204 (2) | 0.0906 (16) | |
H13A | 0.6308 | 0.3549 | −0.2602 | 0.136* | |
H13B | 0.7535 | 0.3670 | −0.2380 | 0.136* | |
H13C | 0.6834 | 0.4586 | −0.2204 | 0.136* | |
C14 | 0.7533 (3) | 0.2386 (2) | 0.40085 (19) | 0.0375 (7) | |
C15 | 0.7005 (3) | 0.2065 (2) | 0.46546 (18) | 0.0383 (7) | |
C16 | 0.7613 (3) | 0.1972 (3) | 0.5502 (2) | 0.0480 (9) | |
H16 | 0.7273 | 0.1786 | 0.5927 | 0.058* | |
C17 | 0.8689 (3) | 0.2137 (3) | 0.5762 (2) | 0.0545 (10) | |
C18 | 0.9191 (3) | 0.2410 (3) | 0.5146 (2) | 0.0488 (9) | |
H18 | 0.9916 | 0.2509 | 0.5306 | 0.059* | |
C19 | 0.8638 (3) | 0.2547 (2) | 0.42646 (19) | 0.0385 (7) | |
C20 | 0.9266 (3) | 0.2875 (3) | 0.3692 (2) | 0.0508 (9) | |
H20 | 0.9986 | 0.2931 | 0.3935 | 0.061* | |
C21 | 0.9732 (3) | 0.3423 (4) | 0.2417 (3) | 0.0973 (17) | |
H21A | 0.9601 | 0.4125 | 0.2225 | 0.146* | |
H21B | 0.9687 | 0.2983 | 0.1924 | 0.146* | |
H21C | 1.0422 | 0.3371 | 0.2802 | 0.146* | |
C22 | 0.9275 (4) | 0.2029 (4) | 0.6718 (2) | 0.0847 (15) | |
H22A | 0.9060 | 0.1403 | 0.6948 | 0.127* | |
H22B | 0.9114 | 0.2610 | 0.7038 | 0.127* | |
H22C | 1.0019 | 0.2007 | 0.6768 | 0.127* | |
C23 | 0.5821 (3) | 0.1862 (3) | 0.44128 (19) | 0.0462 (9) | |
C24 | 0.5221 (3) | 0.2844 (3) | 0.4044 (2) | 0.0563 (10) | |
H24A | 0.5358 | 0.3375 | 0.4480 | 0.084* | |
H24B | 0.4480 | 0.2699 | 0.3877 | 0.084* | |
H24C | 0.5448 | 0.3071 | 0.3546 | 0.084* | |
C25 | 0.5557 (3) | 0.0979 (3) | 0.3742 (2) | 0.0659 (11) | |
H25A | 0.5784 | 0.1164 | 0.3233 | 0.099* | |
H25B | 0.4810 | 0.0862 | 0.3586 | 0.099* | |
H25C | 0.5912 | 0.0360 | 0.3990 | 0.099* | |
C26 | 0.5414 (3) | 0.1537 (3) | 0.5202 (2) | 0.0734 (12) | |
H26A | 0.5769 | 0.0919 | 0.5452 | 0.110* | |
H26B | 0.4670 | 0.1410 | 0.5019 | 0.110* | |
H26C | 0.5549 | 0.2079 | 0.5628 | 0.110* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Co1 | 0.0520 (3) | 0.0486 (3) | 0.0333 (3) | 0.0033 (2) | 0.0163 (2) | 0.0073 (2) |
O1 | 0.0784 (18) | 0.0398 (14) | 0.0393 (12) | 0.0056 (12) | 0.0274 (12) | 0.0109 (10) |
O2 | 0.0432 (14) | 0.0612 (15) | 0.0271 (11) | −0.0032 (12) | 0.0084 (9) | 0.0057 (10) |
N1 | 0.065 (2) | 0.0425 (17) | 0.0360 (14) | 0.0005 (14) | 0.0171 (13) | 0.0007 (12) |
N2 | 0.0476 (18) | 0.064 (2) | 0.0504 (17) | 0.0015 (15) | 0.0215 (14) | 0.0160 (14) |
C1 | 0.043 (2) | 0.0417 (19) | 0.0333 (16) | −0.0040 (15) | 0.0138 (14) | 0.0020 (14) |
C2 | 0.044 (2) | 0.0413 (19) | 0.0359 (16) | −0.0020 (16) | 0.0153 (14) | −0.0013 (14) |
C3 | 0.054 (2) | 0.057 (2) | 0.0339 (17) | −0.0065 (18) | 0.0170 (15) | −0.0068 (16) |
C4 | 0.072 (3) | 0.060 (2) | 0.0326 (17) | 0.001 (2) | 0.0165 (17) | 0.0088 (17) |
C5 | 0.071 (3) | 0.043 (2) | 0.0424 (18) | 0.0019 (19) | 0.0127 (17) | 0.0119 (16) |
C6 | 0.054 (2) | 0.0373 (19) | 0.0350 (16) | −0.0007 (16) | 0.0120 (15) | 0.0053 (14) |
C7 | 0.068 (3) | 0.0348 (19) | 0.0469 (19) | 0.0038 (17) | 0.0141 (17) | 0.0048 (15) |
C8 | 0.132 (4) | 0.054 (3) | 0.058 (2) | 0.015 (3) | 0.035 (3) | −0.007 (2) |
C9 | 0.082 (3) | 0.042 (2) | 0.055 (2) | 0.006 (2) | 0.031 (2) | 0.0001 (17) |
C10 | 0.101 (4) | 0.074 (3) | 0.071 (3) | 0.041 (3) | 0.040 (3) | 0.023 (2) |
C11 | 0.121 (4) | 0.045 (3) | 0.104 (3) | −0.016 (2) | 0.048 (3) | 0.004 (2) |
C12 | 0.166 (5) | 0.057 (3) | 0.072 (3) | 0.022 (3) | 0.048 (3) | −0.008 (2) |
C13 | 0.150 (5) | 0.085 (3) | 0.042 (2) | 0.010 (3) | 0.034 (2) | 0.021 (2) |
C14 | 0.045 (2) | 0.0342 (18) | 0.0341 (17) | −0.0001 (15) | 0.0122 (14) | −0.0009 (14) |
C15 | 0.048 (2) | 0.0379 (18) | 0.0316 (15) | 0.0020 (15) | 0.0141 (14) | 0.0014 (13) |
C16 | 0.060 (2) | 0.057 (2) | 0.0309 (16) | 0.0022 (19) | 0.0178 (16) | 0.0031 (15) |
C17 | 0.060 (3) | 0.066 (3) | 0.0322 (17) | 0.011 (2) | 0.0014 (17) | −0.0006 (16) |
C18 | 0.040 (2) | 0.056 (2) | 0.047 (2) | 0.0061 (17) | 0.0047 (16) | −0.0037 (17) |
C19 | 0.042 (2) | 0.0359 (18) | 0.0388 (17) | 0.0053 (15) | 0.0116 (15) | 0.0026 (14) |
C20 | 0.038 (2) | 0.056 (2) | 0.058 (2) | 0.0017 (17) | 0.0116 (17) | 0.0071 (18) |
C21 | 0.060 (3) | 0.152 (5) | 0.088 (3) | −0.002 (3) | 0.034 (2) | 0.051 (3) |
C22 | 0.077 (3) | 0.127 (4) | 0.039 (2) | 0.004 (3) | −0.006 (2) | 0.001 (2) |
C23 | 0.050 (2) | 0.056 (2) | 0.0362 (16) | −0.0122 (17) | 0.0177 (15) | 0.0030 (15) |
C24 | 0.047 (2) | 0.072 (3) | 0.053 (2) | 0.0016 (19) | 0.0184 (17) | 0.0000 (18) |
C25 | 0.068 (3) | 0.062 (3) | 0.069 (2) | −0.020 (2) | 0.019 (2) | −0.008 (2) |
C26 | 0.068 (3) | 0.098 (3) | 0.063 (2) | −0.014 (3) | 0.032 (2) | 0.012 (2) |
Co1—O2 | 1.898 (2) | C12—H12B | 0.9600 |
Co1—O1 | 1.902 (2) | C12—H12C | 0.9600 |
Co1—N2 | 1.967 (3) | C13—H13A | 0.9600 |
Co1—N1 | 1.975 (3) | C13—H13B | 0.9600 |
O1—C1 | 1.321 (3) | C13—H13C | 0.9600 |
O2—C14 | 1.320 (3) | C14—C19 | 1.420 (4) |
N1—C7 | 1.285 (4) | C14—C15 | 1.436 (4) |
N1—C8 | 1.474 (4) | C15—C16 | 1.388 (4) |
N2—C20 | 1.289 (4) | C15—C23 | 1.527 (5) |
N2—C21 | 1.475 (5) | C16—C17 | 1.384 (5) |
C1—C6 | 1.415 (5) | C16—H16 | 0.9300 |
C1—C2 | 1.427 (4) | C17—C18 | 1.357 (5) |
C2—C3 | 1.382 (4) | C17—C22 | 1.528 (4) |
C2—C9 | 1.524 (5) | C18—C19 | 1.418 (4) |
C3—C4 | 1.388 (5) | C18—H18 | 0.9300 |
C3—H3 | 0.9300 | C19—C20 | 1.435 (4) |
C4—C5 | 1.370 (5) | C20—H20 | 0.9300 |
C4—C13 | 1.528 (4) | C21—H21A | 0.9600 |
C5—C6 | 1.416 (4) | C21—H21B | 0.9600 |
C5—H5 | 0.9300 | C21—H21C | 0.9600 |
C6—C7 | 1.444 (4) | C22—H22A | 0.9600 |
C7—H7 | 0.9300 | C22—H22B | 0.9600 |
C8—H8A | 0.9600 | C22—H22C | 0.9600 |
C8—H8B | 0.9600 | C23—C24 | 1.532 (5) |
C8—H8C | 0.9600 | C23—C26 | 1.541 (4) |
C9—C10 | 1.542 (5) | C23—C25 | 1.542 (5) |
C9—C11 | 1.543 (5) | C24—H24A | 0.9600 |
C9—C12 | 1.546 (5) | C24—H24B | 0.9600 |
C10—H10A | 0.9600 | C24—H24C | 0.9600 |
C10—H10B | 0.9600 | C25—H25A | 0.9600 |
C10—H10C | 0.9600 | C25—H25B | 0.9600 |
C11—H11A | 0.9600 | C25—H25C | 0.9600 |
C11—H11B | 0.9600 | C26—H26A | 0.9600 |
C11—H11C | 0.9600 | C26—H26B | 0.9600 |
C12—H12A | 0.9600 | C26—H26C | 0.9600 |
O2—Co1—O1 | 123.68 (10) | H12B—C12—H12C | 109.5 |
O2—Co1—N2 | 95.01 (10) | C4—C13—H13A | 109.5 |
O1—Co1—N2 | 111.34 (11) | C4—C13—H13B | 109.5 |
O2—Co1—N1 | 118.84 (10) | H13A—C13—H13B | 109.5 |
O1—Co1—N1 | 94.42 (9) | C4—C13—H13C | 109.5 |
N2—Co1—N1 | 114.81 (12) | H13A—C13—H13C | 109.5 |
C1—O1—Co1 | 126.9 (2) | H13B—C13—H13C | 109.5 |
C14—O2—Co1 | 127.8 (2) | O2—C14—C19 | 122.4 (3) |
C7—N1—C8 | 117.2 (3) | O2—C14—C15 | 119.0 (3) |
C7—N1—Co1 | 121.7 (2) | C19—C14—C15 | 118.6 (3) |
C8—N1—Co1 | 121.0 (2) | C16—C15—C14 | 117.1 (3) |
C20—N2—C21 | 117.7 (3) | C16—C15—C23 | 122.0 (3) |
C20—N2—Co1 | 122.9 (2) | C14—C15—C23 | 120.8 (3) |
C21—N2—Co1 | 119.4 (2) | C17—C16—C15 | 124.9 (3) |
O1—C1—C6 | 121.9 (3) | C17—C16—H16 | 117.6 |
O1—C1—C2 | 119.1 (3) | C15—C16—H16 | 117.6 |
C6—C1—C2 | 119.0 (3) | C18—C17—C16 | 117.9 (3) |
C3—C2—C1 | 117.6 (3) | C18—C17—C22 | 121.8 (4) |
C3—C2—C9 | 122.3 (3) | C16—C17—C22 | 120.3 (3) |
C1—C2—C9 | 120.1 (3) | C17—C18—C19 | 121.6 (3) |
C2—C3—C4 | 124.3 (3) | C17—C18—H18 | 119.2 |
C2—C3—H3 | 117.9 | C19—C18—H18 | 119.2 |
C4—C3—H3 | 117.9 | C18—C19—C14 | 119.8 (3) |
C5—C4—C3 | 118.0 (3) | C18—C19—C20 | 115.5 (3) |
C5—C4—C13 | 121.2 (4) | C14—C19—C20 | 124.6 (3) |
C3—C4—C13 | 120.8 (3) | N2—C20—C19 | 127.1 (3) |
C4—C5—C6 | 121.2 (3) | N2—C20—H20 | 116.5 |
C4—C5—H5 | 119.4 | C19—C20—H20 | 116.5 |
C6—C5—H5 | 119.4 | N2—C21—H21A | 109.5 |
C1—C6—C5 | 119.8 (3) | N2—C21—H21B | 109.5 |
C1—C6—C7 | 124.4 (3) | H21A—C21—H21B | 109.5 |
C5—C6—C7 | 115.9 (3) | N2—C21—H21C | 109.5 |
N1—C7—C6 | 127.5 (3) | H21A—C21—H21C | 109.5 |
N1—C7—H7 | 116.3 | H21B—C21—H21C | 109.5 |
C6—C7—H7 | 116.3 | C17—C22—H22A | 109.5 |
N1—C8—H8A | 109.5 | C17—C22—H22B | 109.5 |
N1—C8—H8B | 109.5 | H22A—C22—H22B | 109.5 |
H8A—C8—H8B | 109.5 | C17—C22—H22C | 109.5 |
N1—C8—H8C | 109.5 | H22A—C22—H22C | 109.5 |
H8A—C8—H8C | 109.5 | H22B—C22—H22C | 109.5 |
H8B—C8—H8C | 109.5 | C15—C23—C24 | 110.3 (3) |
C2—C9—C10 | 110.0 (3) | C15—C23—C26 | 112.4 (3) |
C2—C9—C11 | 110.1 (3) | C24—C23—C26 | 106.7 (3) |
C10—C9—C11 | 110.4 (3) | C15—C23—C25 | 109.9 (3) |
C2—C9—C12 | 112.6 (3) | C24—C23—C25 | 110.2 (3) |
C10—C9—C12 | 106.4 (3) | C26—C23—C25 | 107.2 (3) |
C11—C9—C12 | 107.3 (3) | C23—C24—H24A | 109.5 |
C9—C10—H10A | 109.5 | C23—C24—H24B | 109.5 |
C9—C10—H10B | 109.5 | H24A—C24—H24B | 109.5 |
H10A—C10—H10B | 109.5 | C23—C24—H24C | 109.5 |
C9—C10—H10C | 109.5 | H24A—C24—H24C | 109.5 |
H10A—C10—H10C | 109.5 | H24B—C24—H24C | 109.5 |
H10B—C10—H10C | 109.5 | C23—C25—H25A | 109.5 |
C9—C11—H11A | 109.5 | C23—C25—H25B | 109.5 |
C9—C11—H11B | 109.5 | H25A—C25—H25B | 109.5 |
H11A—C11—H11B | 109.5 | C23—C25—H25C | 109.5 |
C9—C11—H11C | 109.5 | H25A—C25—H25C | 109.5 |
H11A—C11—H11C | 109.5 | H25B—C25—H25C | 109.5 |
H11B—C11—H11C | 109.5 | C23—C26—H26A | 109.5 |
C9—C12—H12A | 109.5 | C23—C26—H26B | 109.5 |
C9—C12—H12B | 109.5 | H26A—C26—H26B | 109.5 |
H12A—C12—H12B | 109.5 | C23—C26—H26C | 109.5 |
C9—C12—H12C | 109.5 | H26A—C26—H26C | 109.5 |
H12A—C12—H12C | 109.5 | H26B—C26—H26C | 109.5 |
O2—Co1—O1—C1 | 149.3 (2) | Co1—N1—C7—C6 | 2.3 (5) |
N2—Co1—O1—C1 | −98.8 (3) | C1—C6—C7—N1 | 8.3 (6) |
N1—Co1—O1—C1 | 20.1 (3) | C5—C6—C7—N1 | −172.4 (3) |
O1—Co1—O2—C14 | 122.9 (3) | C3—C2—C9—C10 | 117.9 (4) |
N2—Co1—O2—C14 | 3.1 (3) | C1—C2—C9—C10 | −62.2 (4) |
N1—Co1—O2—C14 | −118.9 (3) | C3—C2—C9—C11 | −120.3 (4) |
O2—Co1—N1—C7 | −145.6 (3) | C1—C2—C9—C11 | 59.7 (4) |
O1—Co1—N1—C7 | −13.0 (3) | C3—C2—C9—C12 | −0.6 (5) |
N2—Co1—N1—C7 | 103.0 (3) | C1—C2—C9—C12 | 179.4 (3) |
O2—Co1—N1—C8 | 37.1 (3) | Co1—O2—C14—C19 | −3.3 (4) |
O1—Co1—N1—C8 | 169.8 (3) | Co1—O2—C14—C15 | 176.7 (2) |
N2—Co1—N1—C8 | −74.2 (3) | O2—C14—C15—C16 | −177.5 (3) |
O2—Co1—N2—C20 | −0.7 (3) | C19—C14—C15—C16 | 2.5 (4) |
O1—Co1—N2—C20 | −129.9 (3) | O2—C14—C15—C23 | 1.1 (4) |
N1—Co1—N2—C20 | 124.4 (3) | C19—C14—C15—C23 | −178.9 (3) |
O2—Co1—N2—C21 | 177.8 (3) | C14—C15—C16—C17 | −2.0 (5) |
O1—Co1—N2—C21 | 48.6 (3) | C23—C15—C16—C17 | 179.4 (3) |
N1—Co1—N2—C21 | −57.1 (3) | C15—C16—C17—C18 | 0.0 (5) |
Co1—O1—C1—C6 | −15.5 (4) | C15—C16—C17—C22 | 179.0 (4) |
Co1—O1—C1—C2 | 164.6 (2) | C16—C17—C18—C19 | 1.4 (5) |
O1—C1—C2—C3 | −177.8 (3) | C22—C17—C18—C19 | −177.6 (4) |
C6—C1—C2—C3 | 2.3 (5) | C17—C18—C19—C14 | −0.8 (5) |
O1—C1—C2—C9 | 2.3 (5) | C17—C18—C19—C20 | 177.6 (3) |
C6—C1—C2—C9 | −177.6 (3) | O2—C14—C19—C18 | 178.7 (3) |
C1—C2—C3—C4 | −1.4 (5) | C15—C14—C19—C18 | −1.2 (5) |
C9—C2—C3—C4 | 178.5 (4) | O2—C14—C19—C20 | 0.5 (5) |
C2—C3—C4—C5 | −1.0 (6) | C15—C14—C19—C20 | −179.5 (3) |
C2—C3—C4—C13 | 179.7 (4) | C21—N2—C20—C19 | 180.0 (4) |
C3—C4—C5—C6 | 2.5 (6) | Co1—N2—C20—C19 | −1.5 (5) |
C13—C4—C5—C6 | −178.2 (4) | C18—C19—C20—N2 | −176.2 (3) |
O1—C1—C6—C5 | 179.2 (3) | C14—C19—C20—N2 | 2.1 (6) |
C2—C1—C6—C5 | −0.9 (5) | C16—C15—C23—C24 | 118.1 (3) |
O1—C1—C6—C7 | −1.5 (5) | C14—C15—C23—C24 | −60.5 (4) |
C2—C1—C6—C7 | 178.4 (3) | C16—C15—C23—C26 | −0.9 (5) |
C4—C5—C6—C1 | −1.6 (5) | C14—C15—C23—C26 | −179.5 (3) |
C4—C5—C6—C7 | 179.0 (3) | C16—C15—C23—C25 | −120.2 (3) |
C8—N1—C7—C6 | 179.6 (4) | C14—C15—C23—C25 | 61.2 (4) |