Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007622/ac6157sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007622/ac6157Isup2.hkl |
CCDC reference: 270219
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocaldo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Version 1.05; Farrugia, 1999); software used to prepare material for publication: SHELXL97.
C28H24N4O4S2 | F(000) = 1136 |
Mr = 544.63 | Dx = 1.333 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71065 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 10.8010 (17) Å | θ = 11.4–16.0° |
b = 14.279 (4) Å | µ = 0.24 mm−1 |
c = 18.074 (3) Å | T = 296 K |
β = 103.230 (13)° | Prismatic, colorless |
V = 2713.5 (10) Å3 | 0.35 × 0.30 × 0.25 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 2870 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.016 |
Graphite monochromator | θmax = 25.2°, θmin = 1.8° |
ω/2θ scans | h = 0→12 |
Absorption correction: empirical (using intensity measurements) (North et al., 1968) | k = −1→17 |
Tmin = 0.890, Tmax = 0.943 | l = −21→21 |
5598 measured reflections | 3 standard reflections every 3600 min |
4877 independent reflections | intensity decay: <1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.037 | H-atom parameters constrained |
wR(F2) = 0.118 | w = 1/[σ2(Fo2) + (0.0506P)2 + 0.7918P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max < 0.001 |
4877 reflections | Δρmax = 0.23 e Å−3 |
346 parameters | Δρmin = −0.20 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0024 (5) |
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 | 0.65740 (6) | −0.12422 (5) | 0.33654 (3) | 0.0703 (2) | |
S2 | 0.41765 (6) | 0.10139 (5) | 0.15493 (4) | 0.0695 (2) | |
O1 | 0.76047 (17) | −0.06444 (16) | 0.36889 (10) | 0.0907 (6) | |
O2 | 0.67074 (19) | −0.22297 (14) | 0.34273 (11) | 0.0905 (6) | |
O3 | 0.29336 (18) | 0.07892 (13) | 0.16315 (12) | 0.0877 (6) | |
O4 | 0.5050 (2) | 0.14726 (14) | 0.21452 (11) | 0.0954 (6) | |
N1 | 0.61703 (19) | −0.09624 (15) | 0.24432 (11) | 0.0707 (6) | |
N2 | 0.50190 (19) | −0.13907 (15) | 0.20616 (11) | 0.0677 (5) | |
N3 | 0.48080 (19) | −0.00104 (15) | 0.13659 (13) | 0.0769 (6) | |
N4 | 0.6162 (2) | 0.00467 (16) | 0.14396 (14) | 0.0783 (6) | |
C1 | 0.4333 (3) | −0.1576 (2) | 0.37610 (15) | 0.0776 (7) | |
H1 | 0.4456 | −0.2202 | 0.3654 | 0.093* | |
C2 | 0.3271 (3) | −0.1312 (2) | 0.40121 (16) | 0.0863 (8) | |
H2 | 0.2684 | −0.1765 | 0.4071 | 0.104* | |
C3 | 0.3062 (3) | −0.0407 (3) | 0.41745 (16) | 0.0857 (8) | |
C4 | 0.3940 (4) | 0.0245 (2) | 0.4075 (2) | 0.0847 (11) | |
H4 | 0.3812 | 0.0871 | 0.4181 | 0.126* | |
C5 | 0.5017 (3) | 0.0000 (2) | 0.38196 (18) | 0.0933 (9) | |
H5 | 0.5598 | 0.0454 | 0.3753 | 0.112* | |
C6 | 0.5207 (2) | −0.09155 (18) | 0.36697 (13) | 0.0647 (6) | |
C7 | 0.4341 (2) | −0.08736 (17) | 0.15599 (13) | 0.0600 (6) | |
C8 | 0.6797 (2) | −0.03842 (16) | 0.20286 (13) | 0.0597 (6) | |
C9 | 0.4083 (2) | 0.16451 (17) | 0.07126 (14) | 0.0641 (6) | |
C10 | 0.5077 (3) | 0.22069 (19) | 0.06363 (17) | 0.0803 (8) | |
H10 | 0.5815 | 0.2239 | 0.1020 | 0.096* | |
C11 | 0.4956 (4) | 0.2723 (2) | −0.0022 (2) | 0.0979 (10) | |
H11 | 0.5627 | 0.3105 | −0.0078 | 0.117* | |
C12 | 0.3871 (4) | 0.2691 (2) | −0.06017 (18) | 0.0939 (10) | |
C13 | 0.2905 (4) | 0.2116 (2) | −0.05083 (18) | 0.0969 (10) | |
H13 | 0.2169 | 0.2080 | −0.0893 | 0.116* | |
C14 | 0.2992 (3) | 0.15879 (19) | 0.01373 (17) | 0.0818 (8) | |
H14 | 0.2327 | 0.1198 | 0.0187 | 0.098* | |
C15 | 0.1893 (3) | −0.0112 (3) | 0.4447 (2) | 0.1295 (14) | |
H15A | 0.1158 | −0.0424 | 0.4151 | 0.194* | |
H15B | 0.1783 | 0.0554 | 0.4391 | 0.194* | |
H15C | 0.2000 | −0.0278 | 0.4973 | 0.194* | |
C16 | 0.3751 (5) | 0.3284 (2) | −0.1305 (2) | 0.1383 (16) | |
H16A | 0.4415 | 0.3121 | −0.1556 | 0.207* | |
H16B | 0.3824 | 0.3933 | −0.1165 | 0.207* | |
H16C | 0.2939 | 0.3173 | −0.1643 | 0.207* | |
C17 | 0.3107 (2) | −0.12169 (19) | 0.11196 (14) | 0.0697 (7) | |
C18 | 0.2417 (3) | −0.1829 (2) | 0.14598 (18) | 0.0855 (8) | |
H18 | 0.2745 | −0.2027 | 0.1956 | 0.103* | |
C19 | 0.1247 (3) | −0.2147 (3) | 0.1070 (3) | 0.1181 (13) | |
H19 | 0.0778 | −0.2548 | 0.1306 | 0.142* | |
C20 | 0.0783 (4) | −0.1877 (4) | 0.0346 (3) | 0.1368 (17) | |
H20 | −0.0006 | −0.2098 | 0.0085 | 0.164* | |
C21 | 0.1450 (4) | −0.1284 (4) | −0.0012 (2) | 0.1291 (14) | |
H21 | 0.1117 | −0.1107 | −0.0513 | 0.155* | |
C22 | 0.2631 (3) | −0.0944 (2) | 0.03766 (17) | 0.0951 (9) | |
H22 | 0.3090 | −0.0538 | 0.0138 | 0.114* | |
C23 | 0.8198 (2) | −0.03523 (17) | 0.21881 (13) | 0.0592 (6) | |
C24 | 0.8936 (2) | −0.11392 (18) | 0.24318 (14) | 0.0676 (6) | |
H24 | 0.8552 | −0.1697 | 0.2522 | 0.081* | |
C25 | 1.0231 (3) | −0.1091 (2) | 0.25391 (15) | 0.0785 (8) | |
H25 | 1.0727 | −0.1616 | 0.2703 | 0.094* | |
C26 | 1.0797 (3) | −0.0270 (2) | 0.24047 (16) | 0.0846 (8) | |
H26 | 1.1677 | −0.0242 | 0.2475 | 0.101* | |
C27 | 1.0082 (3) | 0.0512 (2) | 0.21676 (16) | 0.0827 (8) | |
H27 | 1.0476 | 0.1066 | 0.2080 | 0.099* | |
C28 | 0.8775 (3) | 0.04760 (18) | 0.20585 (14) | 0.0712 (7) | |
H28 | 0.8287 | 0.1006 | 0.1899 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0735 (4) | 0.0809 (5) | 0.0560 (4) | −0.0003 (4) | 0.0138 (3) | 0.0088 (3) |
S2 | 0.0723 (4) | 0.0625 (4) | 0.0745 (4) | 0.0012 (3) | 0.0184 (3) | 0.0017 (3) |
O1 | 0.0768 (12) | 0.1295 (17) | 0.0625 (11) | −0.0226 (12) | 0.0089 (9) | −0.0072 (11) |
O2 | 0.1053 (15) | 0.0791 (13) | 0.0883 (13) | 0.0053 (11) | 0.0247 (11) | 0.0220 (10) |
O3 | 0.0810 (13) | 0.0801 (13) | 0.1139 (15) | 0.0022 (10) | 0.0465 (11) | −0.0009 (11) |
O4 | 0.1203 (16) | 0.0829 (13) | 0.0735 (12) | −0.0118 (12) | 0.0024 (11) | −0.0044 (10) |
N1 | 0.0707 (13) | 0.0836 (14) | 0.0554 (11) | −0.0199 (11) | 0.0092 (10) | 0.0072 (10) |
N2 | 0.0708 (13) | 0.0668 (13) | 0.0627 (12) | −0.0145 (11) | 0.0093 (10) | 0.0034 (11) |
N3 | 0.0618 (13) | 0.0627 (13) | 0.1083 (18) | 0.0034 (10) | 0.0241 (12) | 0.0151 (12) |
N4 | 0.0629 (13) | 0.0759 (15) | 0.0985 (17) | 0.0044 (11) | 0.0235 (12) | 0.0283 (13) |
C1 | 0.089 (2) | 0.0686 (17) | 0.0786 (17) | −0.0044 (15) | 0.0266 (15) | 0.0105 (14) |
C2 | 0.084 (2) | 0.094 (2) | 0.0839 (19) | −0.0162 (17) | 0.0253 (16) | 0.0061 (17) |
C3 | 0.084 (2) | 0.108 (3) | 0.060 (17) | −0.0002 (19) | 0.0176 (15) | −0.0029 (16) |
C4 | 0.128 (3) | 0.076 (2) | 0.086 (3) | 0.007 (2) | 0.041 (2) | −0.0201 (18) |
C5 | 0.109 (2) | 0.0706 (19) | 0.110 (2) | −0.0188 (17) | 0.046 (2) | −0.0119 (17) |
C6 | 0.0773 (16) | 0.0625 (15) | 0.0548 (14) | −0.0031 (13) | 0.0161 (12) | 0.0070 (11) |
C7 | 0.0669 (15) | 0.0566 (14) | 0.0597 (14) | −0.0001 (12) | 0.0211 (12) | −0.0046 (12) |
C8 | 0.0691 (15) | 0.0523 (13) | 0.0615 (14) | −0.0030 (12) | 0.0225 (12) | −0.0006 (11) |
C9 | 0.0590 (14) | 0.0578 (14) | 0.0735 (16) | 0.0066 (12) | 0.0113 (12) | −0.0004 (12) |
C10 | 0.0692 (18) | 0.0720 (17) | 0.097 (2) | −0.0022 (14) | 0.0126 (15) | 0.0134 (16) |
C11 | 0.109 (3) | 0.078 (2) | 0.113 (3) | −0.0036 (18) | 0.039 (2) | 0.0209 (19) |
C12 | 0.144 (3) | 0.0643 (19) | 0.077 (2) | 0.019 (2) | 0.033 (2) | 0.0059 (15) |
C13 | 0.119 (3) | 0.081 (2) | 0.076 (2) | 0.016 (2) | −0.0080 (19) | −0.0001 (17) |
C14 | 0.0735 (18) | 0.0720 (18) | 0.093 (2) | 0.0008 (14) | 0.0036 (15) | −0.0019 (15) |
C15 | 0.113 (3) | 0.186 (4) | 0.098 (2) | 0.020 (3) | 0.043 (2) | −0.019 (3) |
C16 | 0.239 (5) | 0.093 (2) | 0.088 (2) | 0.038 (3) | 0.047 (3) | 0.021 (2) |
C17 | 0.0698 (16) | 0.0717 (17) | 0.0664 (16) | 0.0028 (14) | 0.0130 (13) | −0.0194 (13) |
C18 | 0.0778 (19) | 0.086 (2) | 0.094 (2) | −0.0177 (16) | 0.0220 (16) | −0.0237 (16) |
C19 | 0.091 (2) | 0.136 (3) | 0.128 (3) | −0.035 (2) | 0.028 (2) | −0.058 (3) |
C20 | 0.095 (3) | 0.179 (5) | 0.127 (4) | −0.017 (3) | 0.008 (3) | −0.076 (3) |
C21 | 0.119 (3) | 0.173 (4) | 0.079 (2) | 0.003 (3) | −0.012 (2) | −0.038 (3) |
C22 | 0.099 (2) | 0.111 (2) | 0.0706 (19) | 0.0045 (19) | 0.0095 (17) | −0.0152 (17) |
C23 | 0.0638 (15) | 0.0607 (14) | 0.0550 (13) | −0.0024 (12) | 0.0174 (11) | −0.0013 (11) |
C24 | 0.0689 (16) | 0.0671 (16) | 0.0667 (15) | −0.0022 (13) | 0.0156 (12) | 0.0036 (12) |
C25 | 0.0699 (18) | 0.084 (2) | 0.0808 (18) | 0.0045 (15) | 0.0153 (14) | 0.0089 (15) |
C26 | 0.0659 (17) | 0.111 (2) | 0.0755 (18) | −0.0056 (17) | 0.0131 (14) | 0.0070 (17) |
C27 | 0.0785 (19) | 0.087 (2) | 0.0841 (19) | −0.0205 (16) | 0.0219 (15) | 0.0084 (16) |
C28 | 0.0769 (18) | 0.0651 (16) | 0.0738 (17) | −0.0030 (14) | 0.0219 (14) | 0.0048 (13) |
S1—O1 | 1.4184 (19) | C12—C13 | 1.369 (5) |
S1—O2 | 1.419 (2) | C12—C16 | 1.508 (4) |
S1—N1 | 1.672 (2) | C13—C14 | 1.374 (4) |
S1—C6 | 1.752 (3) | C13—H13 | 0.9300 |
S2—O4 | 1.419 (2) | C14—H14 | 0.9300 |
S2—O3 | 1.4208 (19) | C15—H15A | 0.9599 |
S2—N3 | 1.679 (2) | C15—H15B | 0.9599 |
S2—C9 | 1.743 (3) | C15—H15C | 0.9599 |
N1—C8 | 1.391 (3) | C16—H16A | 0.9599 |
N1—N2 | 1.415 (3) | C16—H16B | 0.9599 |
N2—C7 | 1.265 (3) | C16—H16C | 0.9599 |
N3—C7 | 1.406 (3) | C17—C22 | 1.380 (4) |
N3—N4 | 1.440 (3) | C17—C18 | 1.382 (4) |
N4—C8 | 1.284 (3) | C18—C19 | 1.375 (4) |
C1—C6 | 1.371 (3) | C18—H18 | 0.9300 |
C1—C2 | 1.379 (4) | C19—C20 | 1.346 (6) |
C1—H1 | 0.9300 | C19—H19 | 0.9300 |
C2—C3 | 1.355 (4) | C20—C21 | 1.367 (6) |
C2—H2 | 0.9300 | C20—H20 | 0.9300 |
C3—C4 | 1.370 (4) | C21—C22 | 1.395 (5) |
C3—C15 | 1.516 (4) | C21—H21 | 0.9300 |
C4—C5 | 1.392 (4) | C22—H22 | 0.9300 |
C4—H4 | 0.9300 | C23—C28 | 1.382 (3) |
C5—C6 | 1.359 (4) | C23—C24 | 1.390 (3) |
C5—H5 | 0.9300 | C24—C25 | 1.369 (3) |
C7—C17 | 1.471 (3) | C24—H24 | 0.9300 |
C8—C23 | 1.474 (3) | C25—C26 | 1.369 (4) |
C9—C10 | 1.372 (3) | C25—H25 | 0.9300 |
C9—C14 | 1.384 (3) | C26—C27 | 1.368 (4) |
C10—C11 | 1.381 (4) | C26—H26 | 0.9300 |
C10—H10 | 0.9300 | C27—C28 | 1.381 (4) |
C11—C12 | 1.382 (5) | C27—H27 | 0.9300 |
C11—H11 | 0.9300 | C28—H28 | 0.9300 |
O1—S1—O2 | 120.63 (13) | C11—C12—C16 | 121.0 (4) |
O1—S1—N1 | 105.56 (11) | C12—C13—C14 | 121.9 (3) |
O2—S1—N1 | 108.34 (12) | C12—C13—H13 | 119.0 |
O1—S1—C6 | 110.39 (13) | C14—C13—H13 | 119.0 |
O2—S1—C6 | 108.50 (12) | C13—C14—C9 | 119.1 (3) |
N1—S1—C6 | 101.72 (11) | C13—C14—H14 | 120.5 |
O4—S2—O3 | 120.34 (13) | C9—C14—H14 | 120.5 |
O4—S2—N3 | 108.79 (12) | C3—C15—H15A | 109.5 |
O3—S2—N3 | 105.08 (11) | C3—C15—H15B | 109.5 |
O4—S2—C9 | 108.42 (12) | H15A—C15—H15B | 109.5 |
O3—S2—C9 | 109.82 (12) | C3—C15—H15C | 109.5 |
N3—S2—C9 | 102.97 (12) | H15A—C15—H15C | 109.5 |
C8—N1—N2 | 118.41 (19) | H15B—C15—H15C | 109.5 |
C8—N1—S1 | 129.12 (17) | C12—C16—H16A | 109.5 |
N2—N1—S1 | 112.47 (15) | C12—C16—H16B | 109.5 |
C7—N2—N1 | 113.4 (2) | H16A—C16—H16B | 109.5 |
C7—N3—N4 | 116.16 (19) | C12—C16—H16C | 109.5 |
C7—N3—S2 | 121.97 (17) | H16A—C16—H16C | 109.5 |
N4—N3—S2 | 112.48 (17) | H16B—C16—H16C | 109.5 |
C8—N4—N3 | 112.8 (2) | C22—C17—C18 | 119.5 (3) |
C6—C1—C2 | 119.9 (3) | C22—C17—C7 | 121.5 (3) |
C6—C1—H1 | 120.1 | C18—C17—C7 | 119.0 (2) |
C2—C1—H1 | 120.1 | C19—C18—C17 | 120.5 (3) |
C3—C2—C1 | 121.7 (3) | C19—C18—H18 | 119.8 |
C3—C2—H2 | 119.2 | C17—C18—H18 | 119.8 |
C1—C2—H2 | 119.2 | C20—C19—C18 | 119.8 (4) |
C2—C3—C4 | 117.7 (3) | C20—C19—H19 | 120.1 |
C2—C3—C15 | 121.9 (3) | C18—C19—H19 | 120.1 |
C4—C3—C15 | 120.4 (3) | C19—C20—C21 | 121.2 (4) |
C3—C4—C5 | 121.9 (3) | C19—C20—H20 | 119.4 |
C3—C4—H4 | 119.0 | C21—C20—H20 | 119.4 |
C5—C4—H4 | 119.0 | C20—C21—C22 | 119.8 (4) |
C6—C5—C4 | 119.0 (3) | C20—C21—H21 | 120.1 |
C6—C5—H5 | 120.5 | C22—C21—H21 | 120.1 |
C4—C5—H5 | 120.5 | C17—C22—C21 | 119.1 (4) |
C5—C6—C1 | 119.9 (3) | C17—C22—H22 | 120.5 |
C5—C6—S1 | 119.7 (2) | C21—C22—H22 | 120.5 |
C1—C6—S1 | 120.5 (2) | C28—C23—C24 | 119.8 (2) |
N2—C7—N3 | 120.6 (2) | C28—C23—C8 | 118.4 (2) |
N2—C7—C17 | 119.8 (2) | C24—C23—C8 | 121.7 (2) |
N3—C7—C17 | 119.3 (2) | C25—C24—C23 | 119.8 (2) |
N4—C8—N1 | 119.8 (2) | C25—C24—H24 | 120.1 |
N4—C8—C23 | 118.5 (2) | C23—C24—H24 | 120.1 |
N1—C8—C23 | 121.2 (2) | C24—C25—C26 | 120.1 (3) |
C10—C9—C14 | 120.7 (3) | C24—C25—H25 | 120.0 |
C10—C9—S2 | 119.9 (2) | C26—C25—H25 | 120.0 |
C14—C9—S2 | 119.4 (2) | C27—C26—C25 | 120.7 (3) |
C9—C10—C11 | 118.5 (3) | C27—C26—H26 | 119.7 |
C9—C10—H10 | 120.7 | C25—C26—H26 | 119.7 |
C11—C10—H10 | 120.7 | C26—C27—C28 | 120.0 (3) |
C10—C11—C12 | 122.1 (3) | C26—C27—H27 | 120.0 |
C10—C11—H11 | 119.0 | C28—C27—H27 | 120.0 |
C12—C11—H11 | 119.0 | C27—C28—C23 | 119.6 (3) |
C13—C12—C11 | 117.7 (3) | C27—C28—H28 | 120.2 |
C13—C12—C16 | 121.4 (4) | C23—C28—H28 | 120.2 |
O1—S1—N1—C8 | 9.4 (3) | N2—N1—C8—C23 | −144.2 (2) |
O2—S1—N1—C8 | −121.1 (2) | S1—N1—C8—C23 | 36.2 (3) |
C6—S1—N1—C8 | 124.7 (2) | O4—S2—C9—C10 | 24.1 (2) |
O1—S1—N1—N2 | −170.30 (17) | O3—S2—C9—C10 | 157.4 (2) |
O2—S1—N1—N2 | 59.2 (2) | N3—S2—C9—C10 | −91.0 (2) |
C6—S1—N1—N2 | −55.0 (2) | O4—S2—C9—C14 | −154.5 (2) |
C8—N1—N2—C7 | −36.6 (3) | O3—S2—C9—C14 | −21.2 (2) |
S1—N1—N2—C7 | 143.15 (19) | N3—S2—C9—C14 | 90.3 (2) |
O4—S2—N3—C7 | 108.8 (2) | C14—C9—C10—C11 | 0.9 (4) |
O3—S2—N3—C7 | −21.3 (2) | S2—C9—C10—C11 | −177.8 (2) |
C9—S2—N3—C7 | −136.3 (2) | C9—C10—C11—C12 | 0.1 (5) |
O4—S2—N3—N4 | −36.4 (2) | C10—C11—C12—C13 | −0.7 (5) |
O3—S2—N3—N4 | −166.47 (17) | C10—C11—C12—C16 | 178.3 (3) |
C9—S2—N3—N4 | 78.54 (19) | C11—C12—C13—C14 | 0.4 (5) |
C7—N3—N4—C8 | −38.9 (3) | C16—C12—C13—C14 | −178.6 (3) |
S2—N3—N4—C8 | 108.5 (2) | C12—C13—C14—C9 | 0.5 (5) |
C6—C1—C2—C3 | −0.1 (4) | C10—C9—C14—C13 | −1.2 (4) |
C1—C2—C3—C4 | 0.5 (5) | S2—C9—C14—C13 | 177.5 (2) |
C1—C2—C3—C15 | 179.7 (3) | N2—C7—C17—C22 | −148.2 (3) |
C2—C3—C4—C5 | −0.3 (5) | N3—C7—C17—C22 | 25.6 (4) |
C15—C3—C4—C5 | −179.5 (3) | N2—C7—C17—C18 | 31.6 (4) |
C3—C4—C5—C6 | −0.4 (5) | N3—C7—C17—C18 | −154.6 (2) |
C4—C5—C6—C1 | 0.9 (5) | C22—C17—C18—C19 | −1.6 (4) |
C4—C5—C6—S1 | −178.8 (2) | C7—C17—C18—C19 | 178.6 (3) |
C2—C1—C6—C5 | −0.7 (4) | C17—C18—C19—C20 | 1.4 (5) |
C2—C1—C6—S1 | 179.0 (2) | C18—C19—C20—C21 | −0.4 (7) |
O1—S1—C6—C5 | 31.7 (3) | C19—C20—C21—C22 | −0.4 (7) |
O2—S1—C6—C5 | 165.9 (2) | C18—C17—C22—C21 | 0.8 (4) |
N1—S1—C6—C5 | −80.0 (2) | C7—C17—C22—C21 | −179.4 (3) |
O1—S1—C6—C1 | −148.0 (2) | C20—C21—C22—C17 | 0.2 (6) |
O2—S1—C6—C1 | −13.7 (2) | N4—C8—C23—C28 | 38.9 (3) |
N1—S1—C6—C1 | 100.4 (2) | N1—C8—C23—C28 | −149.4 (2) |
N1—N2—C7—N3 | 7.0 (3) | N4—C8—C23—C24 | −138.3 (3) |
N1—N2—C7—C17 | −179.3 (2) | N1—C8—C23—C24 | 33.4 (3) |
N4—N3—C7—N2 | 30.4 (3) | C28—C23—C24—C25 | −0.3 (4) |
S2—N3—C7—N2 | −113.6 (2) | C8—C23—C24—C25 | 176.9 (2) |
N4—N3—C7—C17 | −143.4 (2) | C23—C24—C25—C26 | −0.2 (4) |
S2—N3—C7—C17 | 72.7 (3) | C24—C25—C26—C27 | 0.4 (4) |
N3—N4—C8—N1 | 10.4 (3) | C25—C26—C27—C28 | −0.3 (5) |
N3—N4—C8—C23 | −177.8 (2) | C26—C27—C28—C23 | −0.2 (4) |
N2—N1—C8—N4 | 27.5 (3) | C24—C23—C28—C27 | 0.5 (4) |
S1—N1—C8—N4 | −152.2 (2) | C8—C23—C28—C27 | −176.8 (2) |