Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030510/ob2040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030510/ob2040Isup2.hkl |
CCDC reference: 621447
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.
C26H36N2O3S | F(000) = 984 |
Mr = 456.63 | Dx = 1.134 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 11.163 (5) Å | Cell parameters from 3267 reflections |
b = 10.422 (4) Å | θ = 2.5–20.9° |
c = 23.031 (10) Å | µ = 0.15 mm−1 |
β = 93.298 (5)° | T = 273 K |
V = 2675.2 (19) Å3 | Tabular, colourless |
Z = 4 | 0.32 × 0.18 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 4727 independent reflections |
Radiation source: fine-focus sealed tube | 3488 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
φ and ω scans | θmax = 25.0°, θmin = 2.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −13→13 |
Tmin = 0.646, Tmax = 1.000 | k = −12→12 |
13998 measured reflections | l = −18→27 |
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) = 0.130 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.048P)2 + 0.7023P] where P = (Fo2 + 2Fc2)/3 |
4727 reflections | (Δ/σ)max = 0.001 |
297 parameters | Δρmax = 0.41 e Å−3 |
0 restraints | Δρmin = −0.19 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 | ||
S1 | 0.13845 (4) | 0.47509 (5) | 0.10450 (2) | 0.05454 (17) | |
O1 | −0.08298 (15) | 0.81865 (19) | 0.07935 (8) | 0.0948 (6) | |
O2 | 0.26953 (14) | 0.79192 (14) | 0.16660 (6) | 0.0663 (4) | |
O3 | 0.21744 (12) | 0.43853 (14) | 0.04940 (6) | 0.0629 (4) | |
N1 | 0.09988 (14) | 0.72495 (15) | 0.08915 (7) | 0.0520 (4) | |
N2 | 0.16754 (13) | 0.63024 (15) | 0.12051 (7) | 0.0473 (4) | |
C1 | −0.13918 (19) | 0.5804 (2) | 0.14972 (11) | 0.0692 (6) | |
H1 | −0.1668 | 0.5594 | 0.1121 | 0.083* | |
C2 | −0.1846 (2) | 0.5160 (3) | 0.19648 (12) | 0.0755 (7) | |
C3 | −0.2789 (3) | 0.4121 (3) | 0.18662 (15) | 0.1097 (11) | |
H3A | −0.2675 | 0.3474 | 0.2161 | 0.165* | |
H3B | −0.2714 | 0.3742 | 0.1490 | 0.165* | |
H3C | −0.3573 | 0.4490 | 0.1885 | 0.165* | |
C4 | −0.1419 (2) | 0.5492 (3) | 0.25207 (11) | 0.0745 (7) | |
H4 | −0.1717 | 0.5066 | 0.2836 | 0.089* | |
C5 | −0.0564 (2) | 0.6434 (2) | 0.26221 (10) | 0.0685 (6) | |
C6 | −0.0068 (3) | 0.6738 (3) | 0.32334 (11) | 0.0961 (9) | |
H6A | −0.0534 | 0.6297 | 0.3509 | 0.144* | |
H6B | −0.0111 | 0.7646 | 0.3299 | 0.144* | |
H6C | 0.0752 | 0.6461 | 0.3279 | 0.144* | |
C7 | −0.01384 (19) | 0.7074 (2) | 0.21471 (10) | 0.0649 (6) | |
H7 | 0.0421 | 0.7729 | 0.2208 | 0.078* | |
C8 | −0.05320 (17) | 0.6755 (2) | 0.15848 (9) | 0.0588 (5) | |
C9 | −0.01363 (19) | 0.7465 (2) | 0.10611 (10) | 0.0616 (5) | |
C10 | 0.14818 (19) | 0.7860 (2) | 0.03564 (9) | 0.0591 (5) | |
C11 | 0.1455 (3) | 0.9312 (2) | 0.04359 (12) | 0.0872 (8) | |
H11A | 0.0648 | 0.9583 | 0.0493 | 0.131* | |
H11B | 0.1735 | 0.9721 | 0.0096 | 0.131* | |
H11C | 0.1965 | 0.9546 | 0.0769 | 0.131* | |
C12 | 0.0712 (3) | 0.7427 (3) | −0.01749 (10) | 0.0929 (9) | |
H12A | 0.0751 | 0.6510 | −0.0208 | 0.139* | |
H12B | 0.1004 | 0.7814 | −0.0518 | 0.139* | |
H12C | −0.0105 | 0.7684 | −0.0134 | 0.139* | |
C13 | 0.2770 (2) | 0.7441 (2) | 0.02902 (11) | 0.0737 (6) | |
H13A | 0.3250 | 0.7671 | 0.0633 | 0.111* | |
H13B | 0.3077 | 0.7859 | −0.0041 | 0.111* | |
H13C | 0.2796 | 0.6528 | 0.0237 | 0.111* | |
C14 | 0.32747 (19) | 0.3602 (2) | 0.05839 (12) | 0.0739 (7) | |
C15 | 0.4208 (2) | 0.4300 (3) | 0.09356 (15) | 0.1097 (11) | |
H15A | 0.4307 | 0.5142 | 0.0776 | 0.165* | |
H15B | 0.4953 | 0.3841 | 0.0931 | 0.165* | |
H15C | 0.3972 | 0.4373 | 0.1329 | 0.165* | |
C16 | 0.2928 (3) | 0.2333 (3) | 0.0833 (2) | 0.161 (2) | |
H16A | 0.3553 | 0.1719 | 0.0779 | 0.241* | |
H16B | 0.2196 | 0.2040 | 0.0637 | 0.241* | |
H16C | 0.2813 | 0.2429 | 0.1240 | 0.241* | |
C17 | 0.3639 (3) | 0.3433 (4) | −0.00365 (15) | 0.1378 (15) | |
H17A | 0.3767 | 0.4260 | −0.0206 | 0.207* | |
H17B | 0.3014 | 0.2991 | −0.0259 | 0.207* | |
H17C | 0.4366 | 0.2941 | −0.0036 | 0.207* | |
C18 | 0.24637 (16) | 0.6781 (2) | 0.16553 (8) | 0.0506 (5) | |
C19 | 0.29471 (16) | 0.5907 (2) | 0.21221 (8) | 0.0523 (5) | |
C20 | 0.41123 (18) | 0.6153 (2) | 0.23475 (9) | 0.0653 (6) | |
H20 | 0.4578 | 0.6768 | 0.2174 | 0.078* | |
C21 | 0.4576 (2) | 0.5485 (3) | 0.28292 (10) | 0.0736 (7) | |
H21 | 0.5362 | 0.5638 | 0.2967 | 0.088* | |
C22 | 0.3896 (2) | 0.4599 (2) | 0.31083 (9) | 0.0668 (6) | |
C23 | 0.4367 (3) | 0.3980 (3) | 0.36695 (10) | 0.0899 (8) | |
H23A | 0.4044 | 0.3119 | 0.3694 | 0.108* | |
H23B | 0.5234 | 0.3915 | 0.3671 | 0.108* | |
C24 | 0.4029 (3) | 0.4739 (3) | 0.41850 (11) | 0.1069 (10) | |
H24A | 0.4319 | 0.5602 | 0.4153 | 0.160* | |
H24B | 0.4379 | 0.4353 | 0.4533 | 0.160* | |
H24C | 0.3171 | 0.4749 | 0.4200 | 0.160* | |
C25 | 0.2740 (2) | 0.4363 (2) | 0.28825 (10) | 0.0677 (6) | |
H25 | 0.2269 | 0.3763 | 0.3063 | 0.081* | |
C26 | 0.22701 (19) | 0.4998 (2) | 0.23950 (9) | 0.0605 (5) | |
H26 | 0.1495 | 0.4815 | 0.2249 | 0.073* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0494 (3) | 0.0486 (3) | 0.0653 (3) | −0.0034 (2) | 0.0005 (2) | −0.0015 (2) |
O1 | 0.0745 (10) | 0.1082 (14) | 0.1016 (13) | 0.0328 (10) | 0.0036 (10) | 0.0422 (11) |
O2 | 0.0814 (10) | 0.0546 (9) | 0.0614 (9) | −0.0111 (8) | −0.0095 (7) | 0.0008 (7) |
O3 | 0.0598 (8) | 0.0615 (9) | 0.0672 (9) | 0.0055 (7) | 0.0020 (7) | −0.0122 (7) |
N1 | 0.0539 (9) | 0.0501 (10) | 0.0514 (9) | 0.0032 (7) | −0.0037 (7) | 0.0082 (7) |
N2 | 0.0477 (8) | 0.0446 (9) | 0.0489 (9) | 0.0007 (7) | −0.0045 (7) | 0.0033 (7) |
C1 | 0.0569 (12) | 0.0789 (16) | 0.0706 (15) | 0.0042 (11) | −0.0066 (11) | 0.0064 (12) |
C2 | 0.0552 (12) | 0.0795 (17) | 0.0915 (19) | 0.0006 (11) | 0.0024 (12) | 0.0149 (14) |
C3 | 0.0884 (19) | 0.122 (3) | 0.117 (2) | −0.0321 (18) | −0.0059 (18) | 0.023 (2) |
C4 | 0.0631 (13) | 0.0868 (18) | 0.0749 (17) | 0.0091 (13) | 0.0149 (12) | 0.0145 (13) |
C5 | 0.0646 (13) | 0.0788 (16) | 0.0633 (14) | 0.0139 (12) | 0.0132 (11) | 0.0020 (12) |
C6 | 0.112 (2) | 0.115 (2) | 0.0632 (16) | 0.0066 (18) | 0.0165 (15) | −0.0124 (15) |
C7 | 0.0579 (12) | 0.0684 (15) | 0.0688 (15) | 0.0066 (11) | 0.0078 (10) | −0.0012 (11) |
C8 | 0.0499 (11) | 0.0613 (13) | 0.0653 (13) | 0.0134 (10) | 0.0034 (10) | 0.0067 (11) |
C9 | 0.0582 (12) | 0.0624 (13) | 0.0634 (13) | 0.0091 (10) | −0.0027 (10) | 0.0064 (11) |
C10 | 0.0698 (13) | 0.0583 (13) | 0.0487 (11) | −0.0034 (10) | −0.0012 (10) | 0.0082 (9) |
C11 | 0.116 (2) | 0.0611 (16) | 0.0848 (18) | −0.0026 (14) | 0.0122 (16) | 0.0180 (13) |
C12 | 0.0984 (18) | 0.126 (2) | 0.0520 (14) | −0.0119 (17) | −0.0111 (13) | 0.0039 (15) |
C13 | 0.0758 (15) | 0.0807 (17) | 0.0656 (14) | −0.0064 (13) | 0.0127 (12) | 0.0142 (12) |
C14 | 0.0555 (12) | 0.0678 (15) | 0.0985 (18) | 0.0062 (11) | 0.0048 (12) | −0.0144 (13) |
C15 | 0.0646 (15) | 0.137 (3) | 0.125 (3) | 0.0212 (17) | −0.0181 (16) | −0.048 (2) |
C16 | 0.097 (2) | 0.080 (2) | 0.309 (6) | 0.0294 (19) | 0.036 (3) | 0.049 (3) |
C17 | 0.102 (2) | 0.191 (4) | 0.121 (3) | 0.038 (2) | 0.010 (2) | −0.072 (3) |
C18 | 0.0509 (10) | 0.0557 (13) | 0.0450 (10) | −0.0027 (9) | 0.0014 (8) | 0.0010 (9) |
C19 | 0.0506 (10) | 0.0608 (12) | 0.0451 (11) | 0.0023 (9) | −0.0007 (8) | 0.0010 (9) |
C20 | 0.0545 (11) | 0.0870 (17) | 0.0535 (12) | −0.0072 (11) | −0.0038 (10) | 0.0042 (11) |
C21 | 0.0549 (12) | 0.107 (2) | 0.0573 (14) | 0.0070 (12) | −0.0105 (10) | 0.0005 (13) |
C22 | 0.0692 (14) | 0.0821 (16) | 0.0492 (12) | 0.0200 (12) | 0.0021 (10) | 0.0053 (11) |
C23 | 0.1004 (19) | 0.109 (2) | 0.0587 (15) | 0.0286 (17) | −0.0086 (13) | 0.0145 (14) |
C24 | 0.144 (3) | 0.122 (3) | 0.0539 (15) | −0.008 (2) | −0.0011 (17) | 0.0094 (16) |
C25 | 0.0707 (14) | 0.0751 (15) | 0.0572 (13) | 0.0043 (11) | 0.0033 (11) | 0.0158 (11) |
C26 | 0.0540 (11) | 0.0682 (14) | 0.0589 (13) | −0.0015 (10) | −0.0001 (10) | 0.0086 (11) |
S1—O3 | 1.6315 (16) | C12—H12C | 0.9600 |
S1—N2 | 1.6860 (17) | C13—H13A | 0.9600 |
O1—C9 | 1.221 (2) | C13—H13B | 0.9600 |
O2—C18 | 1.214 (2) | C13—H13C | 0.9600 |
O3—C14 | 1.479 (3) | C14—C15 | 1.474 (4) |
N1—C9 | 1.366 (3) | C14—C16 | 1.501 (4) |
N1—N2 | 1.416 (2) | C14—C17 | 1.518 (4) |
N1—C10 | 1.513 (3) | C15—H15A | 0.9600 |
N2—C18 | 1.412 (2) | C15—H15B | 0.9600 |
C1—C8 | 1.386 (3) | C15—H15C | 0.9600 |
C1—C2 | 1.389 (3) | C16—H16A | 0.9600 |
C1—H1 | 0.9300 | C16—H16B | 0.9600 |
C2—C4 | 1.384 (4) | C16—H16C | 0.9600 |
C2—C3 | 1.518 (4) | C17—H17A | 0.9600 |
C3—H3A | 0.9600 | C17—H17B | 0.9600 |
C3—H3B | 0.9600 | C17—H17C | 0.9600 |
C3—H3C | 0.9600 | C18—C19 | 1.487 (3) |
C4—C5 | 1.380 (4) | C19—C26 | 1.385 (3) |
C4—H4 | 0.9300 | C19—C20 | 1.396 (3) |
C5—C7 | 1.388 (3) | C20—C21 | 1.385 (3) |
C5—C6 | 1.516 (4) | C20—H20 | 0.9300 |
C6—H6A | 0.9600 | C21—C22 | 1.378 (3) |
C6—H6B | 0.9600 | C21—H21 | 0.9300 |
C6—H6C | 0.9600 | C22—C25 | 1.385 (3) |
C7—C8 | 1.384 (3) | C22—C23 | 1.512 (3) |
C7—H7 | 0.9300 | C23—C24 | 1.493 (4) |
C8—C9 | 1.503 (3) | C23—H23A | 0.9700 |
C10—C13 | 1.518 (3) | C23—H23B | 0.9700 |
C10—C12 | 1.523 (3) | C24—H24A | 0.9600 |
C10—C11 | 1.525 (3) | C24—H24B | 0.9600 |
C11—H11A | 0.9600 | C24—H24C | 0.9600 |
C11—H11B | 0.9600 | C25—C26 | 1.381 (3) |
C11—H11C | 0.9600 | C25—H25 | 0.9300 |
C12—H12A | 0.9600 | C26—H26 | 0.9300 |
C12—H12B | 0.9600 | ||
O3—S1—N2 | 106.75 (8) | H13A—C13—H13B | 109.5 |
C14—O3—S1 | 120.09 (14) | C10—C13—H13C | 109.5 |
C9—N1—N2 | 116.43 (16) | H13A—C13—H13C | 109.5 |
C9—N1—C10 | 122.95 (16) | H13B—C13—H13C | 109.5 |
N2—N1—C10 | 120.25 (15) | C15—C14—O3 | 111.1 (2) |
C18—N2—N1 | 114.84 (15) | C15—C14—C16 | 114.5 (3) |
C18—N2—S1 | 127.13 (13) | O3—C14—C16 | 108.0 (2) |
N1—N2—S1 | 117.83 (12) | C15—C14—C17 | 110.8 (2) |
C8—C1—C2 | 120.9 (2) | O3—C14—C17 | 101.4 (2) |
C8—C1—H1 | 119.6 | C16—C14—C17 | 110.2 (3) |
C2—C1—H1 | 119.6 | C14—C15—H15A | 109.5 |
C4—C2—C1 | 118.3 (2) | C14—C15—H15B | 109.5 |
C4—C2—C3 | 121.0 (2) | H15A—C15—H15B | 109.5 |
C1—C2—C3 | 120.6 (3) | C14—C15—H15C | 109.5 |
C2—C3—H3A | 109.5 | H15A—C15—H15C | 109.5 |
C2—C3—H3B | 109.5 | H15B—C15—H15C | 109.5 |
H3A—C3—H3B | 109.5 | C14—C16—H16A | 109.5 |
C2—C3—H3C | 109.5 | C14—C16—H16B | 109.5 |
H3A—C3—H3C | 109.5 | H16A—C16—H16B | 109.5 |
H3B—C3—H3C | 109.5 | C14—C16—H16C | 109.5 |
C5—C4—C2 | 122.2 (2) | H16A—C16—H16C | 109.5 |
C5—C4—H4 | 118.9 | H16B—C16—H16C | 109.5 |
C2—C4—H4 | 118.9 | C14—C17—H17A | 109.5 |
C4—C5—C7 | 118.2 (2) | C14—C17—H17B | 109.5 |
C4—C5—C6 | 121.1 (2) | H17A—C17—H17B | 109.5 |
C7—C5—C6 | 120.6 (2) | C14—C17—H17C | 109.5 |
C5—C6—H6A | 109.4 | H17A—C17—H17C | 109.5 |
C5—C6—H6B | 109.5 | H17B—C17—H17C | 109.5 |
H6A—C6—H6B | 109.5 | O2—C18—N2 | 118.89 (17) |
C5—C6—H6C | 109.5 | O2—C18—C19 | 121.07 (17) |
H6A—C6—H6C | 109.5 | N2—C18—C19 | 119.97 (18) |
H6B—C6—H6C | 109.5 | C26—C19—C20 | 118.55 (19) |
C8—C7—C5 | 121.2 (2) | C26—C19—C18 | 124.22 (17) |
C8—C7—H7 | 119.4 | C20—C19—C18 | 116.61 (19) |
C5—C7—H7 | 119.4 | C21—C20—C19 | 120.2 (2) |
C7—C8—C1 | 119.2 (2) | C21—C20—H20 | 119.9 |
C7—C8—C9 | 122.7 (2) | C19—C20—H20 | 119.9 |
C1—C8—C9 | 117.9 (2) | C22—C21—C20 | 121.3 (2) |
O1—C9—N1 | 121.9 (2) | C22—C21—H21 | 119.3 |
O1—C9—C8 | 120.10 (19) | C20—C21—H21 | 119.3 |
N1—C9—C8 | 117.98 (18) | C21—C22—C25 | 118.1 (2) |
N1—C10—C13 | 110.17 (17) | C21—C22—C23 | 120.7 (2) |
N1—C10—C12 | 108.60 (18) | C25—C22—C23 | 121.1 (2) |
C13—C10—C12 | 109.2 (2) | C24—C23—C22 | 111.3 (2) |
N1—C10—C11 | 108.00 (18) | C24—C23—H23A | 109.4 |
C13—C10—C11 | 108.8 (2) | C22—C23—H23A | 109.4 |
C12—C10—C11 | 112.1 (2) | C24—C23—H23B | 109.4 |
C10—C11—H11A | 109.5 | C22—C23—H23B | 109.4 |
C10—C11—H11B | 109.5 | H23A—C23—H23B | 108.0 |
H11A—C11—H11B | 109.5 | C23—C24—H24A | 109.5 |
C10—C11—H11C | 109.5 | C23—C24—H24B | 109.5 |
H11A—C11—H11C | 109.5 | H24A—C24—H24B | 109.5 |
H11B—C11—H11C | 109.5 | C23—C24—H24C | 109.5 |
C10—C12—H12A | 109.5 | H24A—C24—H24C | 109.5 |
C10—C12—H12B | 109.5 | H24B—C24—H24C | 109.5 |
H12A—C12—H12B | 109.5 | C26—C25—C22 | 121.5 (2) |
C10—C12—H12C | 109.5 | C26—C25—H25 | 119.3 |
H12A—C12—H12C | 109.5 | C22—C25—H25 | 119.3 |
H12B—C12—H12C | 109.5 | C25—C26—C19 | 120.4 (2) |
C10—C13—H13A | 109.5 | C25—C26—H26 | 119.8 |
C10—C13—H13B | 109.5 | C19—C26—H26 | 119.8 |
N2—S1—O3—C14 | 104.40 (16) | N2—N1—C10—C13 | −7.8 (2) |
C9—N1—N2—C18 | −96.7 (2) | C9—N1—C10—C12 | −61.0 (3) |
C10—N1—N2—C18 | 90.1 (2) | N2—N1—C10—C12 | 111.7 (2) |
C9—N1—N2—S1 | 78.5 (2) | C9—N1—C10—C11 | 60.7 (3) |
C10—N1—N2—S1 | −94.71 (17) | N2—N1—C10—C11 | −126.5 (2) |
O3—S1—N2—C18 | −100.41 (16) | S1—O3—C14—C15 | −66.2 (3) |
O3—S1—N2—N1 | 85.11 (14) | S1—O3—C14—C16 | 60.2 (3) |
C8—C1—C2—C4 | 0.0 (3) | S1—O3—C14—C17 | 176.1 (2) |
C8—C1—C2—C3 | 179.9 (2) | N1—N2—C18—O2 | −15.1 (2) |
C1—C2—C4—C5 | 0.0 (4) | S1—N2—C18—O2 | 170.29 (15) |
C3—C2—C4—C5 | −179.9 (3) | N1—N2—C18—C19 | 161.91 (16) |
C2—C4—C5—C7 | 0.9 (4) | S1—N2—C18—C19 | −12.7 (2) |
C2—C4—C5—C6 | −177.2 (2) | O2—C18—C19—C26 | 133.8 (2) |
C4—C5—C7—C8 | −1.8 (3) | N2—C18—C19—C26 | −43.2 (3) |
C6—C5—C7—C8 | 176.2 (2) | O2—C18—C19—C20 | −37.1 (3) |
C5—C7—C8—C1 | 1.9 (3) | N2—C18—C19—C20 | 146.01 (19) |
C5—C7—C8—C9 | 177.1 (2) | C26—C19—C20—C21 | 0.8 (3) |
C2—C1—C8—C7 | −0.9 (3) | C18—C19—C20—C21 | 172.2 (2) |
C2—C1—C8—C9 | −176.4 (2) | C19—C20—C21—C22 | −2.1 (4) |
N2—N1—C9—O1 | −174.3 (2) | C20—C21—C22—C25 | 1.9 (4) |
C10—N1—C9—O1 | −1.2 (3) | C20—C21—C22—C23 | −173.5 (2) |
N2—N1—C9—C8 | 4.2 (3) | C21—C22—C23—C24 | 90.1 (3) |
C10—N1—C9—C8 | 177.17 (18) | C25—C22—C23—C24 | −85.2 (3) |
C7—C8—C9—O1 | −106.9 (3) | C21—C22—C25—C26 | −0.5 (4) |
C1—C8—C9—O1 | 68.4 (3) | C23—C22—C25—C26 | 175.0 (2) |
C7—C8—C9—N1 | 74.7 (3) | C22—C25—C26—C19 | −0.8 (4) |
C1—C8—C9—N1 | −110.0 (2) | C20—C19—C26—C25 | 0.6 (3) |
C9—N1—C10—C13 | 179.4 (2) | C18—C19—C26—C25 | −170.1 (2) |