Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000936/ya6277sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000936/ya6277Isup2.hkl |
CCDC reference: 298585
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 (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C30H24N12S3 | Z = 2 |
Mr = 648.82 | F(000) = 672 |
Triclinic, P1 | Dx = 1.404 Mg m−3 |
Hall symbol: -P 1 | Melting point: 425 K |
a = 10.0160 (19) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.323 (2) Å | Cell parameters from 2083 reflections |
c = 15.379 (3) Å | θ = 2.3–22.5° |
α = 68.488 (3)° | µ = 0.28 mm−1 |
β = 71.162 (3)° | T = 294 K |
γ = 84.523 (3)° | Block, colourless |
V = 1535.2 (5) Å3 | 0.28 × 0.24 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 5403 independent reflections |
Radiation source: fine-focus sealed tube | 3377 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.925, Tmax = 0.972 | k = −11→13 |
7852 measured reflections | l = −18→18 |
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)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.094 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.028P)2 + 0.2486P] where P = (Fo2 + 2Fc2)/3 |
5403 reflections | (Δ/σ)max = 0.005 |
406 parameters | Δρmax = 0.25 e Å−3 |
0 restraints | Δρmin = −0.25 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 | 0.08780 (8) | 0.28478 (7) | 0.36733 (5) | 0.0504 (2) | |
S2 | 0.55027 (8) | 0.65753 (7) | 0.16704 (6) | 0.0531 (2) | |
S3 | −0.02785 (8) | 0.76032 (8) | 0.08160 (5) | 0.0520 (2) | |
N1 | −0.0689 (2) | 0.0815 (2) | 0.39369 (15) | 0.0453 (6) | |
N2 | −0.1820 (3) | 0.0106 (2) | 0.46679 (18) | 0.0526 (6) | |
N3 | −0.2225 (2) | 0.0498 (2) | 0.54031 (17) | 0.0501 (6) | |
N4 | −0.1353 (2) | 0.14976 (19) | 0.51535 (15) | 0.0369 (5) | |
N5 | 0.6903 (3) | 0.4320 (3) | 0.19254 (19) | 0.0641 (7) | |
N6 | 0.7620 (3) | 0.3611 (3) | 0.2558 (2) | 0.0816 (9) | |
N7 | 0.7597 (3) | 0.4123 (3) | 0.3186 (2) | 0.0722 (8) | |
N8 | 0.6852 (2) | 0.5202 (2) | 0.29746 (17) | 0.0499 (6) | |
N9 | −0.1454 (2) | 0.8225 (2) | −0.06588 (16) | 0.0491 (6) | |
N10 | −0.2480 (3) | 0.9004 (3) | −0.09320 (17) | 0.0589 (7) | |
N11 | −0.3033 (3) | 0.9620 (2) | −0.03475 (18) | 0.0559 (7) | |
N12 | −0.2347 (2) | 0.9246 (2) | 0.03487 (15) | 0.0407 (6) | |
C1 | 0.2208 (3) | 0.3905 (2) | 0.17462 (17) | 0.0363 (6) | |
C2 | 0.1284 (3) | 0.4643 (3) | 0.12696 (18) | 0.0393 (7) | |
H2 | 0.0391 | 0.4316 | 0.1409 | 0.047* | |
C3 | 0.1670 (3) | 0.5852 (3) | 0.05933 (17) | 0.0382 (6) | |
C4 | 0.3005 (3) | 0.6331 (2) | 0.03989 (17) | 0.0394 (7) | |
H4 | 0.3272 | 0.7147 | −0.0054 | 0.047* | |
C5 | 0.3944 (3) | 0.5622 (3) | 0.08628 (17) | 0.0366 (6) | |
C6 | 0.3534 (3) | 0.4398 (2) | 0.15338 (17) | 0.0370 (6) | |
H6 | 0.4162 | 0.3906 | 0.1843 | 0.044* | |
C7 | 0.1702 (3) | 0.2612 (2) | 0.25130 (17) | 0.0471 (7) | |
H7A | 0.2490 | 0.2048 | 0.2554 | 0.056* | |
H7B | 0.1028 | 0.2241 | 0.2348 | 0.056* | |
C8 | −0.0423 (3) | 0.1670 (2) | 0.42571 (18) | 0.0359 (6) | |
C9 | −0.1483 (3) | 0.2171 (2) | 0.58047 (18) | 0.0348 (6) | |
C10 | −0.1505 (3) | 0.3475 (3) | 0.54498 (19) | 0.0435 (7) | |
H10 | −0.1459 | 0.3913 | 0.4797 | 0.052* | |
C11 | −0.1595 (3) | 0.4129 (3) | 0.6063 (2) | 0.0495 (8) | |
H11 | −0.1593 | 0.5012 | 0.5823 | 0.059* | |
C12 | −0.1687 (3) | 0.3477 (3) | 0.7029 (2) | 0.0536 (8) | |
H12 | −0.1749 | 0.3919 | 0.7444 | 0.064* | |
C13 | −0.1689 (3) | 0.2175 (3) | 0.7384 (2) | 0.0591 (9) | |
H13 | −0.1766 | 0.1738 | 0.8042 | 0.071* | |
C14 | −0.1578 (3) | 0.1504 (3) | 0.67724 (19) | 0.0490 (7) | |
H14 | −0.1567 | 0.0621 | 0.7010 | 0.059* | |
C15 | 0.5367 (3) | 0.6173 (3) | 0.06552 (19) | 0.0509 (8) | |
H15A | 0.5552 | 0.6932 | 0.0068 | 0.061* | |
H15B | 0.6082 | 0.5565 | 0.0526 | 0.061* | |
C16 | 0.6438 (3) | 0.5306 (3) | 0.2198 (2) | 0.0465 (7) | |
C17 | 0.6662 (3) | 0.6036 (3) | 0.3514 (2) | 0.0478 (7) | |
C18 | 0.5339 (3) | 0.6382 (3) | 0.3940 (2) | 0.0717 (10) | |
H18 | 0.4553 | 0.6081 | 0.3880 | 0.086* | |
C19 | 0.5180 (4) | 0.7184 (4) | 0.4460 (3) | 0.0837 (11) | |
H19 | 0.4287 | 0.7442 | 0.4740 | 0.100* | |
C20 | 0.6352 (5) | 0.7600 (3) | 0.4560 (3) | 0.0777 (11) | |
H20 | 0.6250 | 0.8125 | 0.4921 | 0.093* | |
C21 | 0.7664 (4) | 0.7240 (3) | 0.4131 (3) | 0.0731 (10) | |
H21 | 0.8453 | 0.7528 | 0.4196 | 0.088* | |
C22 | 0.7830 (3) | 0.6461 (3) | 0.3607 (2) | 0.0614 (9) | |
H22 | 0.8727 | 0.6219 | 0.3315 | 0.074* | |
C23 | 0.0647 (3) | 0.6640 (3) | 0.0093 (2) | 0.0518 (8) | |
H23A | −0.0016 | 0.6095 | 0.0065 | 0.062* | |
H23B | 0.1149 | 0.7179 | −0.0573 | 0.062* | |
C24 | −0.1389 (3) | 0.8389 (2) | 0.01359 (19) | 0.0397 (7) | |
C25 | −0.2785 (3) | 0.9709 (2) | 0.11470 (19) | 0.0424 (7) | |
C26 | −0.4189 (3) | 0.9923 (3) | 0.1525 (2) | 0.0627 (9) | |
H26 | −0.4853 | 0.9753 | 0.1278 | 0.075* | |
C27 | −0.4594 (4) | 1.0394 (3) | 0.2276 (3) | 0.0856 (12) | |
H27 | −0.5542 | 1.0544 | 0.2538 | 0.103* | |
C28 | −0.3627 (5) | 1.0646 (3) | 0.2646 (3) | 0.0836 (12) | |
H28 | −0.3915 | 1.0969 | 0.3151 | 0.100* | |
C29 | −0.2227 (4) | 1.0418 (3) | 0.2266 (2) | 0.0712 (10) | |
H29 | −0.1567 | 1.0580 | 0.2519 | 0.085* | |
C30 | −0.1796 (3) | 0.9952 (3) | 0.1512 (2) | 0.0543 (8) | |
H30 | −0.0848 | 0.9802 | 0.1252 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0686 (5) | 0.0476 (5) | 0.0347 (4) | −0.0206 (4) | −0.0063 (4) | −0.0174 (3) |
S2 | 0.0533 (5) | 0.0590 (5) | 0.0605 (5) | 0.0016 (4) | −0.0261 (4) | −0.0290 (4) |
S3 | 0.0518 (5) | 0.0704 (6) | 0.0471 (5) | 0.0180 (4) | −0.0270 (4) | −0.0299 (4) |
N1 | 0.0534 (16) | 0.0452 (15) | 0.0441 (14) | −0.0039 (12) | −0.0170 (12) | −0.0207 (12) |
N2 | 0.0546 (16) | 0.0492 (16) | 0.0612 (16) | −0.0095 (13) | −0.0154 (13) | −0.0275 (13) |
N3 | 0.0480 (15) | 0.0470 (15) | 0.0571 (16) | −0.0128 (12) | −0.0098 (12) | −0.0229 (13) |
N4 | 0.0415 (14) | 0.0348 (13) | 0.0368 (13) | −0.0036 (10) | −0.0115 (11) | −0.0148 (10) |
N5 | 0.0658 (18) | 0.0673 (19) | 0.0741 (19) | 0.0149 (15) | −0.0293 (15) | −0.0387 (16) |
N6 | 0.082 (2) | 0.083 (2) | 0.096 (2) | 0.0307 (18) | −0.0389 (19) | −0.0465 (19) |
N7 | 0.071 (2) | 0.076 (2) | 0.081 (2) | 0.0257 (16) | −0.0371 (17) | −0.0355 (17) |
N8 | 0.0436 (15) | 0.0606 (18) | 0.0524 (15) | 0.0063 (13) | −0.0192 (12) | −0.0253 (13) |
N9 | 0.0499 (15) | 0.0621 (17) | 0.0426 (14) | 0.0027 (13) | −0.0221 (12) | −0.0206 (12) |
N10 | 0.0641 (18) | 0.0711 (19) | 0.0504 (16) | 0.0096 (15) | −0.0315 (14) | −0.0218 (14) |
N11 | 0.0590 (17) | 0.0609 (18) | 0.0541 (16) | 0.0100 (13) | −0.0324 (14) | −0.0169 (14) |
N12 | 0.0445 (14) | 0.0420 (14) | 0.0397 (13) | −0.0015 (11) | −0.0195 (11) | −0.0131 (11) |
C1 | 0.0421 (17) | 0.0380 (16) | 0.0290 (14) | −0.0024 (13) | −0.0048 (12) | −0.0168 (12) |
C2 | 0.0340 (16) | 0.0519 (19) | 0.0370 (15) | −0.0041 (13) | −0.0074 (13) | −0.0234 (14) |
C3 | 0.0421 (17) | 0.0472 (18) | 0.0318 (15) | 0.0054 (14) | −0.0150 (13) | −0.0195 (13) |
C4 | 0.0488 (18) | 0.0364 (16) | 0.0299 (14) | −0.0035 (14) | −0.0078 (13) | −0.0112 (12) |
C5 | 0.0353 (16) | 0.0478 (18) | 0.0275 (14) | −0.0044 (13) | −0.0054 (12) | −0.0166 (13) |
C6 | 0.0410 (17) | 0.0427 (17) | 0.0329 (15) | 0.0082 (13) | −0.0145 (12) | −0.0188 (13) |
C7 | 0.060 (2) | 0.0383 (17) | 0.0397 (16) | −0.0013 (14) | −0.0064 (14) | −0.0177 (13) |
C8 | 0.0471 (17) | 0.0328 (16) | 0.0343 (15) | 0.0003 (12) | −0.0189 (13) | −0.0138 (12) |
C9 | 0.0322 (15) | 0.0397 (17) | 0.0347 (15) | −0.0047 (12) | −0.0072 (12) | −0.0171 (13) |
C10 | 0.0482 (18) | 0.0435 (18) | 0.0408 (16) | 0.0003 (14) | −0.0132 (13) | −0.0177 (14) |
C11 | 0.055 (2) | 0.0404 (18) | 0.055 (2) | −0.0007 (14) | −0.0106 (15) | −0.0251 (15) |
C12 | 0.054 (2) | 0.066 (2) | 0.0493 (19) | −0.0051 (16) | −0.0051 (15) | −0.0376 (17) |
C13 | 0.074 (2) | 0.068 (2) | 0.0350 (17) | −0.0096 (18) | −0.0093 (15) | −0.0211 (16) |
C14 | 0.062 (2) | 0.0407 (18) | 0.0412 (17) | −0.0034 (14) | −0.0121 (15) | −0.0134 (14) |
C15 | 0.0440 (18) | 0.069 (2) | 0.0423 (17) | −0.0087 (15) | −0.0101 (14) | −0.0226 (15) |
C16 | 0.0371 (17) | 0.055 (2) | 0.0503 (18) | −0.0047 (14) | −0.0109 (14) | −0.0227 (15) |
C17 | 0.0453 (19) | 0.056 (2) | 0.0467 (17) | −0.0017 (15) | −0.0211 (15) | −0.0166 (15) |
C18 | 0.048 (2) | 0.104 (3) | 0.091 (3) | 0.0065 (19) | −0.0280 (19) | −0.062 (2) |
C19 | 0.071 (3) | 0.109 (3) | 0.101 (3) | 0.020 (2) | −0.034 (2) | −0.070 (3) |
C20 | 0.107 (3) | 0.075 (3) | 0.074 (2) | −0.007 (2) | −0.044 (2) | −0.036 (2) |
C21 | 0.072 (3) | 0.084 (3) | 0.073 (2) | −0.023 (2) | −0.035 (2) | −0.022 (2) |
C22 | 0.048 (2) | 0.079 (2) | 0.059 (2) | −0.0112 (17) | −0.0210 (16) | −0.0194 (18) |
C23 | 0.057 (2) | 0.058 (2) | 0.0490 (17) | 0.0115 (15) | −0.0238 (15) | −0.0252 (15) |
C24 | 0.0361 (16) | 0.0448 (18) | 0.0388 (16) | −0.0024 (13) | −0.0134 (13) | −0.0134 (13) |
C25 | 0.0475 (19) | 0.0325 (16) | 0.0443 (17) | 0.0003 (13) | −0.0125 (14) | −0.0119 (13) |
C26 | 0.057 (2) | 0.063 (2) | 0.078 (2) | 0.0150 (17) | −0.0240 (18) | −0.0373 (19) |
C27 | 0.072 (3) | 0.086 (3) | 0.099 (3) | 0.017 (2) | −0.009 (2) | −0.053 (2) |
C28 | 0.111 (4) | 0.073 (3) | 0.069 (3) | 0.008 (2) | −0.012 (2) | −0.044 (2) |
C29 | 0.094 (3) | 0.067 (2) | 0.064 (2) | −0.007 (2) | −0.029 (2) | −0.0299 (19) |
C30 | 0.059 (2) | 0.057 (2) | 0.0516 (19) | −0.0061 (16) | −0.0185 (16) | −0.0220 (16) |
S1—C8 | 1.727 (3) | C9—C10 | 1.374 (3) |
S1—C7 | 1.815 (3) | C9—C14 | 1.376 (3) |
S2—C16 | 1.726 (3) | C10—C11 | 1.375 (3) |
S2—C15 | 1.826 (3) | C10—H10 | 0.9300 |
S3—C24 | 1.733 (3) | C11—C12 | 1.371 (4) |
S3—C23 | 1.822 (3) | C11—H11 | 0.9300 |
N1—C8 | 1.317 (3) | C12—C13 | 1.372 (4) |
N1—N2 | 1.371 (3) | C12—H12 | 0.9300 |
N2—N3 | 1.295 (3) | C13—C14 | 1.383 (4) |
N3—N4 | 1.359 (3) | C13—H13 | 0.9300 |
N4—C8 | 1.347 (3) | C14—H14 | 0.9300 |
N4—C9 | 1.435 (3) | C15—H15A | 0.9700 |
N5—C16 | 1.326 (3) | C15—H15B | 0.9700 |
N5—N6 | 1.369 (3) | C17—C18 | 1.366 (4) |
N6—N7 | 1.290 (3) | C17—C22 | 1.373 (4) |
N7—N8 | 1.359 (3) | C18—C19 | 1.383 (4) |
N8—C16 | 1.349 (3) | C18—H18 | 0.9300 |
N8—C17 | 1.434 (3) | C19—C20 | 1.378 (5) |
N9—C24 | 1.324 (3) | C19—H19 | 0.9300 |
N9—N10 | 1.358 (3) | C20—C21 | 1.366 (5) |
N10—N11 | 1.291 (3) | C20—H20 | 0.9300 |
N11—N12 | 1.373 (3) | C21—C22 | 1.364 (4) |
N12—C24 | 1.349 (3) | C21—H21 | 0.9300 |
N12—C25 | 1.434 (3) | C22—H22 | 0.9300 |
C1—C6 | 1.382 (3) | C23—H23A | 0.9700 |
C1—C2 | 1.390 (3) | C23—H23B | 0.9700 |
C1—C7 | 1.510 (3) | C25—C26 | 1.373 (4) |
C2—C3 | 1.379 (3) | C25—C30 | 1.377 (4) |
C2—H2 | 0.9300 | C26—C27 | 1.376 (4) |
C3—C4 | 1.390 (3) | C26—H26 | 0.9300 |
C3—C23 | 1.506 (3) | C27—C28 | 1.367 (5) |
C4—C5 | 1.380 (3) | C27—H27 | 0.9300 |
C4—H4 | 0.9300 | C28—C29 | 1.374 (5) |
C5—C6 | 1.393 (3) | C28—H28 | 0.9300 |
C5—C15 | 1.501 (3) | C29—C30 | 1.375 (4) |
C6—H6 | 0.9300 | C29—H29 | 0.9300 |
C7—H7A | 0.9700 | C30—H30 | 0.9300 |
C7—H7B | 0.9700 | ||
C8—S1—C7 | 101.39 (12) | C12—C13—C14 | 120.7 (3) |
C16—S2—C15 | 100.66 (14) | C12—C13—H13 | 119.7 |
C24—S3—C23 | 99.17 (13) | C14—C13—H13 | 119.7 |
C8—N1—N2 | 105.4 (2) | C9—C14—C13 | 118.5 (3) |
N3—N2—N1 | 111.4 (2) | C9—C14—H14 | 120.7 |
N2—N3—N4 | 105.9 (2) | C13—C14—H14 | 120.7 |
C8—N4—N3 | 108.4 (2) | C5—C15—S2 | 112.71 (18) |
C8—N4—C9 | 130.0 (2) | C5—C15—H15A | 109.1 |
N3—N4—C9 | 121.6 (2) | S2—C15—H15A | 109.1 |
C16—N5—N6 | 105.5 (3) | C5—C15—H15B | 109.1 |
N7—N6—N5 | 111.2 (3) | S2—C15—H15B | 109.1 |
N6—N7—N8 | 106.6 (2) | H15A—C15—H15B | 107.8 |
C16—N8—N7 | 108.0 (2) | N5—C16—N8 | 108.7 (3) |
C16—N8—C17 | 130.5 (3) | N5—C16—S2 | 128.4 (2) |
N7—N8—C17 | 121.4 (2) | N8—C16—S2 | 122.9 (2) |
C24—N9—N10 | 105.4 (2) | C18—C17—C22 | 120.9 (3) |
N11—N10—N9 | 111.8 (2) | C18—C17—N8 | 120.3 (3) |
N10—N11—N12 | 106.2 (2) | C22—C17—N8 | 118.7 (3) |
C24—N12—N11 | 107.2 (2) | C17—C18—C19 | 119.4 (3) |
C24—N12—C25 | 132.9 (2) | C17—C18—H18 | 120.3 |
N11—N12—C25 | 119.8 (2) | C19—C18—H18 | 120.3 |
C6—C1—C2 | 119.0 (2) | C20—C19—C18 | 119.6 (4) |
C6—C1—C7 | 122.2 (2) | C20—C19—H19 | 120.2 |
C2—C1—C7 | 118.7 (2) | C18—C19—H19 | 120.2 |
C3—C2—C1 | 121.1 (2) | C21—C20—C19 | 120.0 (3) |
C3—C2—H2 | 119.4 | C21—C20—H20 | 120.0 |
C1—C2—H2 | 119.4 | C19—C20—H20 | 120.0 |
C2—C3—C4 | 118.7 (2) | C22—C21—C20 | 120.7 (3) |
C2—C3—C23 | 120.2 (2) | C22—C21—H21 | 119.7 |
C4—C3—C23 | 121.0 (2) | C20—C21—H21 | 119.7 |
C5—C4—C3 | 121.5 (2) | C21—C22—C17 | 119.4 (3) |
C5—C4—H4 | 119.3 | C21—C22—H22 | 120.3 |
C3—C4—H4 | 119.3 | C17—C22—H22 | 120.3 |
C4—C5—C6 | 118.6 (2) | C3—C23—S3 | 106.95 (17) |
C4—C5—C15 | 120.4 (2) | C3—C23—H23A | 110.3 |
C6—C5—C15 | 121.0 (2) | S3—C23—H23A | 110.3 |
C1—C6—C5 | 121.0 (2) | C3—C23—H23B | 110.3 |
C1—C6—H6 | 119.5 | S3—C23—H23B | 110.3 |
C5—C6—H6 | 119.5 | H23A—C23—H23B | 108.6 |
C1—C7—S1 | 106.64 (17) | N9—C24—N12 | 109.4 (2) |
C1—C7—H7A | 110.4 | N9—C24—S3 | 125.5 (2) |
S1—C7—H7A | 110.4 | N12—C24—S3 | 125.1 (2) |
C1—C7—H7B | 110.4 | C26—C25—C30 | 121.0 (3) |
S1—C7—H7B | 110.4 | C26—C25—N12 | 119.1 (3) |
H7A—C7—H7B | 108.6 | C30—C25—N12 | 119.8 (3) |
N1—C8—N4 | 108.9 (2) | C25—C26—C27 | 118.6 (3) |
N1—C8—S1 | 128.1 (2) | C25—C26—H26 | 120.7 |
N4—C8—S1 | 123.00 (19) | C27—C26—H26 | 120.7 |
C10—C9—C14 | 121.0 (2) | C28—C27—C26 | 121.2 (4) |
C10—C9—N4 | 119.4 (2) | C28—C27—H27 | 119.4 |
C14—C9—N4 | 119.6 (2) | C26—C27—H27 | 119.4 |
C11—C10—C9 | 119.8 (2) | C27—C28—C29 | 119.5 (3) |
C11—C10—H10 | 120.1 | C27—C28—H28 | 120.2 |
C9—C10—H10 | 120.1 | C29—C28—H28 | 120.2 |
C12—C11—C10 | 119.9 (3) | C30—C29—C28 | 120.4 (3) |
C12—C11—H11 | 120.1 | C30—C29—H29 | 119.8 |
C10—C11—H11 | 120.1 | C28—C29—H29 | 119.8 |
C13—C12—C11 | 120.1 (3) | C29—C30—C25 | 119.3 (3) |
C13—C12—H12 | 119.9 | C29—C30—H30 | 120.4 |
C11—C12—H12 | 119.9 | C25—C30—H30 | 120.4 |
C8—N1—N2—N3 | −0.4 (3) | C4—C5—C15—S2 | 106.8 (2) |
N1—N2—N3—N4 | 0.5 (3) | C6—C5—C15—S2 | −72.3 (3) |
N2—N3—N4—C8 | −0.5 (3) | C16—S2—C15—C5 | 102.0 (2) |
N2—N3—N4—C9 | −179.4 (2) | N6—N5—C16—N8 | −0.2 (3) |
C16—N5—N6—N7 | 0.2 (4) | N6—N5—C16—S2 | 177.9 (2) |
N5—N6—N7—N8 | −0.1 (4) | N7—N8—C16—N5 | 0.1 (3) |
N6—N7—N8—C16 | 0.0 (3) | C17—N8—C16—N5 | 177.6 (3) |
N6—N7—N8—C17 | −177.8 (3) | N7—N8—C16—S2 | −178.1 (2) |
C24—N9—N10—N11 | −0.1 (3) | C17—N8—C16—S2 | −0.6 (4) |
N9—N10—N11—N12 | 0.2 (3) | C15—S2—C16—N5 | −0.5 (3) |
N10—N11—N12—C24 | −0.3 (3) | C15—S2—C16—N8 | 177.4 (2) |
N10—N11—N12—C25 | −176.2 (2) | C16—N8—C17—C18 | 56.4 (4) |
C6—C1—C2—C3 | 0.0 (4) | N7—N8—C17—C18 | −126.4 (3) |
C7—C1—C2—C3 | 177.2 (2) | C16—N8—C17—C22 | −124.6 (3) |
C1—C2—C3—C4 | −0.5 (4) | N7—N8—C17—C22 | 52.6 (4) |
C1—C2—C3—C23 | −179.4 (2) | C22—C17—C18—C19 | 0.8 (5) |
C2—C3—C4—C5 | 0.3 (4) | N8—C17—C18—C19 | 179.8 (3) |
C23—C3—C4—C5 | 179.2 (2) | C17—C18—C19—C20 | −1.5 (6) |
C3—C4—C5—C6 | 0.5 (4) | C18—C19—C20—C21 | 1.3 (6) |
C3—C4—C5—C15 | −178.7 (2) | C19—C20—C21—C22 | −0.6 (5) |
C2—C1—C6—C5 | 0.8 (4) | C20—C21—C22—C17 | −0.1 (5) |
C7—C1—C6—C5 | −176.3 (2) | C18—C17—C22—C21 | −0.1 (5) |
C4—C5—C6—C1 | −1.1 (4) | N8—C17—C22—C21 | −179.0 (3) |
C15—C5—C6—C1 | 178.1 (2) | C2—C3—C23—S3 | 93.3 (3) |
C6—C1—C7—S1 | 89.2 (3) | C4—C3—C23—S3 | −85.5 (3) |
C2—C1—C7—S1 | −88.0 (2) | C24—S3—C23—C3 | −179.05 (19) |
C8—S1—C7—C1 | 147.64 (19) | N10—N9—C24—N12 | −0.1 (3) |
N2—N1—C8—N4 | 0.0 (3) | N10—N9—C24—S3 | 178.6 (2) |
N2—N1—C8—S1 | −180.0 (2) | N11—N12—C24—N9 | 0.2 (3) |
N3—N4—C8—N1 | 0.3 (3) | C25—N12—C24—N9 | 175.3 (2) |
C9—N4—C8—N1 | 179.1 (2) | N11—N12—C24—S3 | −178.48 (19) |
N3—N4—C8—S1 | −179.73 (18) | C25—N12—C24—S3 | −3.3 (4) |
C9—N4—C8—S1 | −1.0 (4) | C23—S3—C24—N9 | 1.1 (3) |
C7—S1—C8—N1 | 1.9 (3) | C23—S3—C24—N12 | 179.6 (2) |
C7—S1—C8—N4 | −178.1 (2) | C24—N12—C25—C26 | −140.5 (3) |
C8—N4—C9—C10 | 49.9 (4) | N11—N12—C25—C26 | 34.1 (4) |
N3—N4—C9—C10 | −131.4 (3) | C24—N12—C25—C30 | 40.5 (4) |
C8—N4—C9—C14 | −129.8 (3) | N11—N12—C25—C30 | −144.8 (2) |
N3—N4—C9—C14 | 48.8 (3) | C30—C25—C26—C27 | 0.3 (5) |
C14—C9—C10—C11 | 1.3 (4) | N12—C25—C26—C27 | −178.6 (3) |
N4—C9—C10—C11 | −178.4 (2) | C25—C26—C27—C28 | −0.1 (5) |
C9—C10—C11—C12 | −1.1 (4) | C26—C27—C28—C29 | −0.4 (6) |
C10—C11—C12—C13 | 0.0 (4) | C27—C28—C29—C30 | 0.6 (5) |
C11—C12—C13—C14 | 0.9 (5) | C28—C29—C30—C25 | −0.4 (5) |
C10—C9—C14—C13 | −0.3 (4) | C26—C25—C30—C29 | −0.1 (4) |
N4—C9—C14—C13 | 179.4 (2) | N12—C25—C30—C29 | 178.8 (2) |
C12—C13—C14—C9 | −0.8 (4) |