Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803023687/lh6119sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803023687/lh6119Isup2.hkl |
CCDC reference: 227019
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.
C21H15Cl2N5O2S | F(000) = 968 |
Mr = 472.34 | Dx = 1.485 Mg m−3 |
Monoclinic, P21/c | Melting point = 495–496 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 20.130 (6) Å | Cell parameters from 886 reflections |
b = 6.357 (2) Å | θ = 3.2–26.0° |
c = 17.394 (5) Å | µ = 0.44 mm−1 |
β = 108.369 (5)° | T = 293 K |
V = 2112.6 (11) Å3 | Block, colorless |
Z = 4 | 0.24 × 0.20 × 0.10 mm |
Bruker SMART CCD area-detector diffractometer | 4299 independent reflections |
Radiation source: fine-focus sealed tube | 2878 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scans | θmax = 26.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −25→13 |
Tmin = 0.825, Tmax = 0.960 | k = −7→7 |
11420 measured reflections | l = −21→21 |
Refinement on F2 | 336 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.119 | (Δ/σ)max < 0.001 |
S = 1.03 | Δρmax = 0.26 e Å−3 |
4299 reflections | Δρmin = −0.24 e Å−3 |
330 parameters |
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 | Occ. (<1) | |
S1 | 0.23947 (4) | 0.90593 (9) | 0.43845 (4) | 0.0445 (2) | |
N1 | 0.12918 (11) | 0.6723 (3) | 0.38539 (12) | 0.0434 (5) | |
N2 | 0.06533 (13) | 0.6393 (4) | 0.32744 (14) | 0.0604 (7) | |
N3 | 0.11655 (15) | 0.9474 (4) | 0.30607 (14) | 0.0607 (7) | |
N4 | 0.25902 (10) | 0.5539 (3) | 0.63284 (11) | 0.0330 (4) | |
N5 | 0.21438 (11) | 1.0824 (3) | 0.62151 (12) | 0.0394 (5) | |
H5 | 0.2231 | 1.2112 | 0.6364 | 0.047* | |
C1 | 0.23347 (12) | 0.6694 (3) | 0.49798 (14) | 0.0323 (5) | |
C2 | 0.16842 (13) | 0.5466 (4) | 0.44840 (14) | 0.0374 (6) | |
C3 | 0.06130 (19) | 0.8070 (6) | 0.28353 (19) | 0.0679 (9) | |
H3 | 0.0225 | 0.8319 | 0.2384 | 0.081* | |
C4 | 0.15774 (14) | 0.8550 (4) | 0.37074 (15) | 0.0444 (6) | |
C5 | 0.22482 (12) | 0.7318 (3) | 0.58196 (13) | 0.0312 (5) | |
C6 | 0.26197 (13) | 0.9492 (3) | 0.60941 (15) | 0.0375 (6) | |
C7 | 0.14864 (13) | 0.9865 (3) | 0.60700 (14) | 0.0360 (5) | |
C8 | 0.08830 (15) | 1.0707 (4) | 0.61679 (17) | 0.0503 (7) | |
H8 | 0.0869 | 1.2089 | 0.6337 | 0.060* | |
C9 | 0.03044 (15) | 0.9419 (5) | 0.60047 (17) | 0.0555 (7) | |
H9 | −0.0113 | 0.9962 | 0.6044 | 0.067* | |
C10 | 0.03293 (14) | 0.7356 (4) | 0.57859 (16) | 0.0499 (7) | |
H10 | −0.0067 | 0.6515 | 0.5690 | 0.060* | |
C11 | 0.09377 (13) | 0.6513 (4) | 0.57072 (14) | 0.0407 (6) | |
H11 | 0.0956 | 0.5107 | 0.5568 | 0.049* | |
C12 | 0.15160 (12) | 0.7784 (3) | 0.58369 (13) | 0.0310 (5) | |
C14 | 0.32372 (12) | 0.5151 (4) | 0.61328 (15) | 0.0405 (6) | |
H14A | 0.3435 | 0.3790 | 0.6333 | 0.049* | |
H14B | 0.3583 | 0.6234 | 0.6361 | 0.049* | |
O1 | 0.15312 (10) | 0.3721 (3) | 0.46249 (11) | 0.0493 (5) | |
O2 | 0.32307 (9) | 0.9875 (3) | 0.61800 (13) | 0.0566 (5) | |
Cl1 | 0.2553 (3) | 0.3761 (7) | 0.3403 (3) | 0.0634 (9) | 0.542 (10) |
Cl2 | 0.4976 (3) | 0.6964 (15) | 0.3305 (4) | 0.140 (2) | 0.542 (10) |
C13 | 0.29955 (13) | 0.5216 (4) | 0.52101 (15) | 0.0400 (6) | 0.542 (10) |
H13 | 0.2805 | 0.3809 | 0.5045 | 0.048* | 0.542 (10) |
C15 | 0.3480 (3) | 0.5637 (10) | 0.4698 (4) | 0.0401 (18) | 0.542 (10) |
C16 | 0.3331 (3) | 0.4959 (9) | 0.3902 (3) | 0.0512 (19) | 0.542 (10) |
C17 | 0.3802 (4) | 0.5349 (10) | 0.3481 (3) | 0.062 (2) | 0.542 (10) |
H17 | 0.3702 | 0.4896 | 0.2948 | 0.075* | 0.542 (10) |
C18 | 0.4422 (3) | 0.6416 (12) | 0.3857 (4) | 0.063 (2) | 0.542 (10) |
C19 | 0.4571 (2) | 0.7093 (11) | 0.4653 (4) | 0.072 (2) | 0.542 (10) |
H19 | 0.4986 | 0.7807 | 0.4905 | 0.087* | 0.542 (10) |
C20 | 0.4100 (3) | 0.6704 (11) | 0.5074 (4) | 0.0582 (19) | 0.542 (10) |
H20 | 0.4200 | 0.7157 | 0.5607 | 0.070* | 0.542 (10) |
Cl1' | 0.2834 (4) | 0.4032 (10) | 0.3523 (4) | 0.0802 (14) | 0.458 (10) |
Cl2' | 0.5225 (3) | 0.8059 (8) | 0.3775 (6) | 0.119 (2) | 0.458 (10) |
C13' | 0.29955 (13) | 0.5216 (4) | 0.52101 (15) | 0.0400 (6) | 0.458 (10) |
H13' | 0.2849 | 0.3801 | 0.5002 | 0.048* | 0.458 (10) |
C15' | 0.3623 (3) | 0.5917 (12) | 0.4919 (5) | 0.042 (2) | 0.458 (10) |
C16' | 0.3559 (3) | 0.5355 (11) | 0.4126 (4) | 0.048 (2) | 0.458 (10) |
C17' | 0.4057 (4) | 0.6016 (11) | 0.3778 (5) | 0.057 (2) | 0.458 (10) |
H17' | 0.4014 | 0.5640 | 0.3247 | 0.069* | 0.458 (10) |
C18' | 0.4619 (3) | 0.7239 (11) | 0.4222 (5) | 0.070 (3) | 0.458 (10) |
C19' | 0.4684 (3) | 0.7801 (10) | 0.5014 (5) | 0.078 (3) | 0.458 (10) |
H19' | 0.5060 | 0.8619 | 0.5311 | 0.093* | 0.458 (10) |
C20' | 0.4186 (4) | 0.7140 (12) | 0.5363 (4) | 0.067 (2) | 0.458 (10) |
H20' | 0.4229 | 0.7516 | 0.5893 | 0.081* | 0.458 (10) |
C21 | 0.27025 (16) | 0.5846 (4) | 0.71935 (15) | 0.0519 (7) | |
H21A | 0.2992 | 0.7060 | 0.7379 | 0.078* | |
H21B | 0.2929 | 0.4628 | 0.7487 | 0.078* | |
H21C | 0.2260 | 0.6051 | 0.7282 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0536 (4) | 0.0335 (3) | 0.0525 (4) | 0.0032 (3) | 0.0254 (3) | 0.0128 (3) |
N1 | 0.0468 (13) | 0.0463 (12) | 0.0343 (12) | 0.0026 (10) | 0.0088 (10) | −0.0015 (10) |
N2 | 0.0570 (16) | 0.0757 (17) | 0.0387 (14) | 0.0088 (13) | 0.0011 (12) | −0.0091 (13) |
N3 | 0.0782 (18) | 0.0654 (16) | 0.0410 (14) | 0.0299 (14) | 0.0221 (13) | 0.0137 (12) |
N4 | 0.0371 (11) | 0.0280 (9) | 0.0330 (11) | −0.0004 (8) | 0.0099 (9) | 0.0014 (8) |
N5 | 0.0523 (13) | 0.0218 (9) | 0.0458 (12) | −0.0038 (9) | 0.0178 (10) | −0.0063 (8) |
C1 | 0.0366 (13) | 0.0260 (10) | 0.0375 (13) | 0.0016 (9) | 0.0164 (11) | 0.0051 (10) |
C2 | 0.0470 (15) | 0.0356 (13) | 0.0331 (13) | −0.0015 (11) | 0.0177 (11) | −0.0048 (10) |
C3 | 0.070 (2) | 0.088 (2) | 0.0388 (17) | 0.0277 (19) | 0.0065 (15) | −0.0047 (17) |
C4 | 0.0567 (17) | 0.0456 (14) | 0.0366 (15) | 0.0149 (13) | 0.0229 (13) | 0.0035 (11) |
C5 | 0.0348 (13) | 0.0239 (10) | 0.0345 (13) | −0.0044 (9) | 0.0103 (10) | −0.0011 (9) |
C6 | 0.0429 (15) | 0.0265 (11) | 0.0410 (15) | −0.0054 (11) | 0.0102 (11) | 0.0008 (10) |
C7 | 0.0460 (14) | 0.0299 (11) | 0.0355 (14) | 0.0009 (11) | 0.0175 (11) | 0.0042 (10) |
C8 | 0.0656 (19) | 0.0383 (13) | 0.0573 (18) | 0.0127 (13) | 0.0338 (15) | 0.0049 (12) |
C9 | 0.0485 (17) | 0.0675 (19) | 0.0609 (19) | 0.0130 (15) | 0.0322 (15) | 0.0114 (15) |
C10 | 0.0391 (15) | 0.0637 (17) | 0.0519 (17) | −0.0068 (13) | 0.0213 (13) | 0.0036 (14) |
C11 | 0.0422 (15) | 0.0425 (13) | 0.0390 (15) | −0.0060 (11) | 0.0148 (12) | −0.0007 (11) |
C12 | 0.0349 (13) | 0.0299 (11) | 0.0291 (12) | 0.0006 (10) | 0.0113 (10) | 0.0018 (9) |
C14 | 0.0342 (14) | 0.0300 (12) | 0.0553 (17) | 0.0002 (10) | 0.0110 (12) | 0.0045 (11) |
O1 | 0.0632 (12) | 0.0366 (9) | 0.0472 (11) | −0.0113 (8) | 0.0162 (9) | −0.0072 (8) |
O2 | 0.0396 (11) | 0.0342 (9) | 0.0937 (16) | −0.0103 (8) | 0.0176 (10) | −0.0037 (9) |
Cl1 | 0.092 (3) | 0.0590 (14) | 0.0448 (13) | 0.0114 (15) | 0.0300 (17) | −0.0024 (9) |
Cl2 | 0.093 (2) | 0.217 (5) | 0.147 (3) | 0.050 (3) | 0.089 (2) | 0.087 (3) |
C13 | 0.0441 (14) | 0.0297 (11) | 0.0512 (16) | 0.0035 (10) | 0.0220 (12) | 0.0042 (11) |
C15 | 0.029 (3) | 0.036 (3) | 0.054 (4) | 0.010 (2) | 0.012 (3) | 0.010 (3) |
C16 | 0.050 (4) | 0.055 (4) | 0.049 (4) | 0.021 (3) | 0.016 (4) | 0.013 (3) |
C17 | 0.064 (4) | 0.076 (4) | 0.057 (4) | 0.037 (4) | 0.033 (4) | 0.023 (3) |
C18 | 0.045 (4) | 0.076 (5) | 0.079 (5) | 0.015 (4) | 0.035 (4) | 0.029 (4) |
C19 | 0.053 (4) | 0.075 (5) | 0.096 (6) | 0.010 (3) | 0.034 (4) | 0.016 (4) |
C20 | 0.040 (4) | 0.065 (4) | 0.078 (4) | −0.002 (3) | 0.030 (3) | 0.010 (3) |
Cl1' | 0.107 (4) | 0.084 (2) | 0.062 (2) | −0.007 (2) | 0.045 (3) | −0.0083 (16) |
Cl2' | 0.101 (3) | 0.120 (3) | 0.179 (5) | 0.024 (2) | 0.106 (3) | 0.064 (3) |
C13' | 0.0441 (14) | 0.0297 (11) | 0.0512 (16) | 0.0035 (10) | 0.0220 (12) | 0.0042 (11) |
C15' | 0.048 (5) | 0.041 (4) | 0.042 (4) | 0.009 (3) | 0.021 (4) | 0.012 (3) |
C16' | 0.048 (4) | 0.057 (4) | 0.047 (5) | 0.016 (3) | 0.026 (4) | 0.008 (4) |
C17' | 0.050 (5) | 0.068 (5) | 0.061 (5) | 0.008 (4) | 0.028 (4) | 0.020 (4) |
C18' | 0.064 (5) | 0.070 (5) | 0.089 (6) | 0.015 (4) | 0.045 (5) | 0.016 (5) |
C19' | 0.064 (5) | 0.068 (5) | 0.106 (6) | −0.007 (4) | 0.035 (4) | 0.015 (5) |
C20' | 0.055 (5) | 0.062 (5) | 0.089 (6) | −0.006 (4) | 0.030 (4) | 0.018 (4) |
C21 | 0.0676 (19) | 0.0469 (15) | 0.0363 (15) | 0.0004 (13) | 0.0094 (13) | 0.0016 (12) |
S1—C4 | 1.726 (3) | C11—H11 | 0.9300 |
S1—C1 | 1.851 (2) | C14—C13 | 1.524 (3) |
N1—C4 | 1.356 (3) | C14—H14A | 0.9700 |
N1—N2 | 1.377 (3) | C14—H14B | 0.9700 |
N1—C2 | 1.385 (3) | Cl1—C16 | 1.710 (4) |
N2—C3 | 1.300 (4) | Cl2—C18 | 1.720 (4) |
N3—C4 | 1.308 (3) | C13—C15 | 1.537 (4) |
N3—C3 | 1.383 (4) | C13—H13 | 0.9800 |
N4—C21 | 1.463 (3) | C15—C16 | 1.3900 |
N4—C14 | 1.467 (3) | C15—C20 | 1.3900 |
N4—C5 | 1.467 (3) | C16—C17 | 1.3900 |
N5—C6 | 1.344 (3) | C17—C18 | 1.3900 |
N5—C7 | 1.406 (3) | C17—H17 | 0.9300 |
N5—H5 | 0.8600 | C18—C19 | 1.3900 |
C1—C2 | 1.535 (3) | C19—C20 | 1.3900 |
C1—C13 | 1.574 (3) | C19—H19 | 0.9300 |
C1—C5 | 1.575 (3) | C20—H20 | 0.9300 |
C2—O1 | 1.197 (3) | Cl1'—C16' | 1.724 (5) |
C3—H3 | 0.9300 | Cl2'—C18' | 1.720 (5) |
C5—C12 | 1.513 (3) | C15'—C16' | 1.3900 |
C5—C6 | 1.572 (3) | C15'—C20' | 1.3900 |
C6—O2 | 1.216 (3) | C16'—C17' | 1.3900 |
C7—C8 | 1.386 (3) | C17'—C18' | 1.3900 |
C7—C12 | 1.391 (3) | C17'—H17' | 0.9300 |
C8—C9 | 1.378 (4) | C18'—C19' | 1.3900 |
C8—H8 | 0.9300 | C19'—C20' | 1.3900 |
C9—C10 | 1.371 (4) | C19'—H19' | 0.9300 |
C9—H9 | 0.9300 | C20'—H20' | 0.9300 |
C10—C11 | 1.383 (3) | C21—H21A | 0.9600 |
C10—H10 | 0.9300 | C21—H21B | 0.9600 |
C11—C12 | 1.376 (3) | C21—H21C | 0.9600 |
C4—S1—C1 | 90.76 (11) | C7—C12—C5 | 108.88 (19) |
C4—N1—N2 | 110.3 (2) | N4—C14—C13 | 103.16 (19) |
C4—N1—C2 | 118.3 (2) | N4—C14—H14A | 111.1 |
N2—N1—C2 | 131.3 (2) | C13—C14—H14A | 111.1 |
C3—N2—N1 | 100.1 (3) | N4—C14—H14B | 111.1 |
C4—N3—C3 | 100.9 (2) | C13—C14—H14B | 111.1 |
C21—N4—C14 | 113.6 (2) | H14A—C14—H14B | 109.1 |
C21—N4—C5 | 114.13 (18) | C14—C13—C15 | 124.4 (3) |
C14—N4—C5 | 105.77 (16) | C14—C13—C1 | 104.36 (18) |
C6—N5—C7 | 112.09 (19) | C15—C13—C1 | 112.9 (3) |
C6—N5—H5 | 124.0 | C14—C13—H13 | 104.4 |
C7—N5—H5 | 124.0 | C15—C13—H13 | 104.4 |
C2—C1—C13 | 110.00 (17) | C1—C13—H13 | 104.4 |
C2—C1—C5 | 108.97 (17) | C16—C15—C20 | 120.0 |
C13—C1—C5 | 104.23 (18) | C16—C15—C13 | 123.1 (3) |
C2—C1—S1 | 107.07 (16) | C20—C15—C13 | 116.9 (3) |
C13—C1—S1 | 115.36 (15) | C15—C16—C17 | 120.0 |
C5—C1—S1 | 111.10 (14) | C15—C16—Cl1 | 121.3 (3) |
O1—C2—N1 | 125.3 (2) | C17—C16—Cl1 | 118.7 (3) |
O1—C2—C1 | 125.8 (2) | C18—C17—C16 | 120.0 |
N1—C2—C1 | 108.89 (19) | C18—C17—H17 | 120.0 |
N2—C3—N3 | 117.9 (3) | C16—C17—H17 | 120.0 |
N2—C3—H3 | 121.1 | C17—C18—C19 | 120.0 |
N3—C3—H3 | 121.1 | C17—C18—Cl2 | 118.7 (3) |
N3—C4—N1 | 110.8 (3) | C19—C18—Cl2 | 121.2 (3) |
N3—C4—S1 | 135.4 (2) | C20—C19—C18 | 120.0 |
N1—C4—S1 | 113.70 (19) | C20—C19—H19 | 120.0 |
N4—C5—C12 | 114.44 (17) | C18—C19—H19 | 120.0 |
N4—C5—C6 | 114.00 (18) | C19—C20—C15 | 120.0 |
C12—C5—C6 | 101.24 (17) | C19—C20—H20 | 120.0 |
N4—C5—C1 | 101.38 (16) | C15—C20—H20 | 120.0 |
C12—C5—C1 | 117.44 (18) | C16'—C15'—C20' | 120.0 |
C6—C5—C1 | 108.78 (17) | C15'—C16'—C17' | 120.0 |
O2—C6—N5 | 126.7 (2) | C15'—C16'—Cl1' | 121.7 (3) |
O2—C6—C5 | 125.4 (2) | C17'—C16'—Cl1' | 118.1 (3) |
N5—C6—C5 | 107.9 (2) | C16'—C17'—C18' | 120.0 |
C8—C7—C12 | 121.5 (2) | C16'—C17'—H17' | 120.0 |
C8—C7—N5 | 128.5 (2) | C18'—C17'—H17' | 120.0 |
C12—C7—N5 | 109.90 (19) | C17'—C18'—C19' | 120.0 |
C9—C8—C7 | 117.5 (2) | C17'—C18'—Cl2' | 119.2 (3) |
C9—C8—H8 | 121.2 | C19'—C18'—Cl2' | 120.8 (3) |
C7—C8—H8 | 121.2 | C20'—C19'—C18' | 120.0 |
C10—C9—C8 | 121.5 (2) | C20'—C19'—H19' | 120.0 |
C10—C9—H9 | 119.2 | C18'—C19'—H19' | 120.0 |
C8—C9—H9 | 119.2 | C19'—C20'—C15' | 120.0 |
C9—C10—C11 | 120.6 (2) | C19'—C20'—H20' | 120.0 |
C9—C10—H10 | 119.7 | C15'—C20'—H20' | 120.0 |
C11—C10—H10 | 119.7 | N4—C21—H21A | 109.5 |
C12—C11—C10 | 119.1 (2) | N4—C21—H21B | 109.5 |
C12—C11—H11 | 120.4 | H21A—C21—H21B | 109.5 |
C10—C11—H11 | 120.4 | N4—C21—H21C | 109.5 |
C11—C12—C7 | 119.6 (2) | H21A—C21—H21C | 109.5 |
C11—C12—C5 | 131.4 (2) | H21B—C21—H21C | 109.5 |
C4—N1—N2—C3 | −0.4 (3) | C7—C8—C9—C10 | 2.7 (4) |
C2—N1—N2—C3 | −174.8 (2) | C8—C9—C10—C11 | −1.3 (4) |
C4—S1—C1—C2 | 9.13 (15) | C9—C10—C11—C12 | −1.2 (4) |
C4—S1—C1—C13 | 131.92 (18) | C10—C11—C12—C7 | 2.1 (3) |
C4—S1—C1—C5 | −109.75 (16) | C10—C11—C12—C5 | 178.1 (2) |
C4—N1—C2—O1 | −171.4 (2) | C8—C7—C12—C11 | −0.7 (4) |
N2—N1—C2—O1 | 2.6 (4) | N5—C7—C12—C11 | 176.5 (2) |
C4—N1—C2—C1 | 9.9 (3) | C8—C7—C12—C5 | −177.5 (2) |
N2—N1—C2—C1 | −176.1 (2) | N5—C7—C12—C5 | −0.4 (3) |
C13—C1—C2—O1 | 43.3 (3) | N4—C5—C12—C11 | −52.6 (3) |
C5—C1—C2—O1 | −70.4 (3) | C6—C5—C12—C11 | −175.6 (2) |
S1—C1—C2—O1 | 169.4 (2) | C1—C5—C12—C11 | 66.1 (3) |
C13—C1—C2—N1 | −138.00 (19) | N4—C5—C12—C7 | 123.8 (2) |
C5—C1—C2—N1 | 108.3 (2) | C6—C5—C12—C7 | 0.7 (2) |
S1—C1—C2—N1 | −11.9 (2) | C1—C5—C12—C7 | −117.5 (2) |
N1—N2—C3—N3 | 0.7 (3) | C21—N4—C14—C13 | −171.89 (18) |
C4—N3—C3—N2 | −0.6 (3) | C5—N4—C14—C13 | −46.0 (2) |
C3—N3—C4—N1 | 0.3 (3) | N4—C14—C13—C15 | 158.6 (3) |
C3—N3—C4—S1 | 177.7 (2) | N4—C14—C13—C1 | 27.2 (2) |
N2—N1—C4—N3 | 0.1 (3) | C2—C1—C13—C14 | −117.87 (19) |
C2—N1—C4—N3 | 175.3 (2) | C5—C1—C13—C14 | −1.2 (2) |
N2—N1—C4—S1 | −177.94 (16) | S1—C1—C13—C14 | 120.91 (17) |
C2—N1—C4—S1 | −2.7 (3) | C2—C1—C13—C15 | 104.3 (3) |
C1—S1—C4—N3 | 178.3 (3) | C5—C1—C13—C15 | −139.0 (3) |
C1—S1—C4—N1 | −4.30 (18) | S1—C1—C13—C15 | −16.9 (4) |
C21—N4—C5—C12 | −62.8 (3) | C14—C13—C15—C16 | 155.6 (3) |
C14—N4—C5—C12 | 171.60 (18) | C1—C13—C15—C16 | −76.5 (4) |
C21—N4—C5—C6 | 53.1 (3) | C14—C13—C15—C20 | −22.8 (4) |
C14—N4—C5—C6 | −72.5 (2) | C1—C13—C15—C20 | 105.1 (3) |
C21—N4—C5—C1 | 169.80 (19) | C20—C15—C16—C17 | 0.0 |
C14—N4—C5—C1 | 44.2 (2) | C13—C15—C16—C17 | −178.3 (5) |
C2—C1—C5—N4 | 92.31 (19) | C20—C15—C16—Cl1 | −176.6 (4) |
C13—C1—C5—N4 | −25.1 (2) | C13—C15—C16—Cl1 | 5.0 (4) |
S1—C1—C5—N4 | −149.96 (14) | C15—C16—C17—C18 | 0.0 |
C2—C1—C5—C12 | −33.1 (2) | Cl1—C16—C17—C18 | 176.7 (4) |
C13—C1—C5—C12 | −150.54 (18) | C16—C17—C18—C19 | 0.0 |
S1—C1—C5—C12 | 84.6 (2) | C16—C17—C18—Cl2 | −177.4 (4) |
C2—C1—C5—C6 | −147.25 (18) | C17—C18—C19—C20 | 0.0 |
C13—C1—C5—C6 | 95.3 (2) | Cl2—C18—C19—C20 | 177.3 (4) |
S1—C1—C5—C6 | −29.5 (2) | C18—C19—C20—C15 | 0.0 |
C7—N5—C6—O2 | −179.3 (2) | C16—C15—C20—C19 | 0.0 |
C7—N5—C6—C5 | 0.6 (3) | C13—C15—C20—C19 | 178.5 (5) |
N4—C5—C6—O2 | 55.7 (3) | C20'—C15'—C16'—C17' | 0.0 |
C12—C5—C6—O2 | 179.1 (2) | C20'—C15'—C16'—Cl1' | −174.4 (4) |
C1—C5—C6—O2 | −56.6 (3) | C15'—C16'—C17'—C18' | 0.0 |
N4—C5—C6—N5 | −124.2 (2) | Cl1'—C16'—C17'—C18' | 174.6 (4) |
C12—C5—C6—N5 | −0.8 (2) | C16'—C17'—C18'—C19' | 0.0 |
C1—C5—C6—N5 | 123.5 (2) | C16'—C17'—C18'—Cl2' | −179.4 (4) |
C6—N5—C7—C8 | 176.7 (2) | C17'—C18'—C19'—C20' | 0.0 |
C6—N5—C7—C12 | −0.2 (3) | Cl2'—C18'—C19'—C20' | 179.4 (4) |
C12—C7—C8—C9 | −1.7 (4) | C18'—C19'—C20'—C15' | 0.0 |
N5—C7—C8—C9 | −178.2 (2) | C16'—C15'—C20'—C19' | 0.0 |