Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806007069/sg2011sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806007069/sg2011Isup2.hkl |
CCDC reference: 605169
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); 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.
C25H26N4O2S | Z = 2 |
Mr = 446.56 | F(000) = 472 |
Triclinic, P1 | Dx = 1.353 Mg m−3 |
a = 9.5216 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.076 (1) Å | Cell parameters from 3408 reflections |
c = 12.5294 (11) Å | θ = 2.5–28.2° |
α = 105.036 (2)° | µ = 0.18 mm−1 |
β = 101.193 (2)° | T = 292 K |
γ = 114.050 (2)° | Block, colorless |
V = 1095.93 (17) Å3 | 0.30 × 0.20 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 3570 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.069 |
Graphite monochromator | θmax = 27.5°, θmin = 1.8° |
φ and ω scans | h = −12→12 |
12852 measured reflections | k = −14→14 |
4978 independent reflections | l = −16→16 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.123 | H-atom parameters constrained |
S = 0.95 | w = 1/[σ2(Fo2) + (0.0632P)2] where P = (Fo2 + 2Fc2)/3 |
4978 reflections | (Δ/σ)max < 0.001 |
310 parameters | Δρmax = 0.24 e Å−3 |
18 restraints | Δρmin = −0.29 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 | Occ. (<1) | |
C1 | −0.0546 (2) | −0.23765 (17) | 0.32994 (14) | 0.0372 (4) | |
C2 | −0.2134 (2) | −0.35648 (18) | 0.32003 (15) | 0.0450 (4) | |
H2A | −0.2175 | −0.4475 | 0.2852 | 0.054* | 0.808 (6) |
H2B | −0.3037 | −0.3558 | 0.2691 | 0.054* | 0.808 (6) |
H2C | −0.2438 | −0.4440 | 0.2563 | 0.054* | 0.192 (6) |
H2D | −0.2994 | −0.3312 | 0.3044 | 0.054* | 0.192 (6) |
C3 | −0.2306 (3) | −0.3394 (4) | 0.4402 (2) | 0.0453 (8) | 0.808 (6) |
H3A | −0.2633 | −0.2670 | 0.4632 | 0.054* | 0.808 (6) |
H3B | −0.3156 | −0.4287 | 0.4360 | 0.054* | 0.808 (6) |
C4 | −0.0724 (3) | −0.2971 (3) | 0.5316 (2) | 0.0450 (8) | 0.808 (6) |
H4A | −0.0395 | −0.3693 | 0.5083 | 0.054* | 0.808 (6) |
H4B | −0.0895 | −0.2928 | 0.6060 | 0.054* | 0.808 (6) |
C3' | −0.191 (2) | −0.3802 (12) | 0.4341 (7) | 0.059 (4) | 0.192 (6) |
H3C | −0.2978 | −0.4423 | 0.4352 | 0.071* | 0.192 (6) |
H3D | −0.1266 | −0.4285 | 0.4377 | 0.071* | 0.192 (6) |
C4' | −0.1095 (11) | −0.2439 (12) | 0.5411 (10) | 0.051 (3) | 0.192 (6) |
H4C | −0.1076 | −0.2659 | 0.6113 | 0.061* | 0.192 (6) |
H4D | −0.1703 | −0.1922 | 0.5367 | 0.061* | 0.192 (6) |
C5 | 0.0646 (2) | −0.15214 (17) | 0.54753 (14) | 0.0419 (4) | |
H5A | 0.0450 | −0.0768 | 0.5890 | 0.050* | 0.808 (6) |
H5B | 0.1683 | −0.1372 | 0.5946 | 0.050* | 0.808 (6) |
H5C | 0.1121 | −0.0561 | 0.6053 | 0.050* | 0.192 (6) |
H5D | 0.1263 | −0.1966 | 0.5738 | 0.050* | 0.192 (6) |
C6 | 0.07304 (19) | −0.14491 (16) | 0.43044 (14) | 0.0338 (4) | |
C7 | 0.20855 (19) | −0.04578 (16) | 0.40860 (13) | 0.0325 (4) | |
C8 | 0.1764 (2) | −0.07016 (17) | 0.28935 (14) | 0.0378 (4) | |
C9 | 0.4224 (2) | 0.10940 (17) | 0.31116 (14) | 0.0380 (4) | |
C10 | 0.5309 (2) | 0.1854 (2) | 0.25124 (16) | 0.0544 (5) | |
H10A | 0.4776 | 0.1383 | 0.1676 | 0.082* | |
H10B | 0.6323 | 0.1838 | 0.2727 | 0.082* | |
H10C | 0.5520 | 0.2826 | 0.2751 | 0.082* | |
C11 | 0.46787 (19) | 0.14936 (16) | 0.43527 (13) | 0.0334 (4) | |
C12 | 0.36193 (19) | 0.07171 (16) | 0.48544 (13) | 0.0315 (4) | |
C13 | 0.6195 (2) | 0.27715 (17) | 0.51428 (15) | 0.0379 (4) | |
C14 | 0.53053 (19) | 0.22325 (16) | 0.67469 (14) | 0.0326 (4) | |
C15 | 0.4310 (2) | 0.18140 (18) | 0.83284 (15) | 0.0458 (4) | |
H15A | 0.4414 | 0.1007 | 0.8418 | 0.055* | |
H15B | 0.3247 | 0.1454 | 0.7754 | 0.055* | |
C16 | 0.4465 (2) | 0.2788 (2) | 0.94908 (16) | 0.0563 (5) | |
H16A | 0.4262 | 0.3542 | 0.9374 | 0.068* | |
H16B | 0.3636 | 0.2247 | 0.9774 | 0.068* | |
C17 | 0.7207 (2) | 0.32217 (19) | 0.88217 (14) | 0.0434 (4) | |
H17A | 0.8061 | 0.3767 | 0.8559 | 0.052* | |
H17B | 0.7384 | 0.2459 | 0.8946 | 0.052* | |
C18 | 0.7259 (2) | 0.4175 (2) | 0.99489 (16) | 0.0539 (5) | |
H18A | 0.8322 | 0.4588 | 1.0543 | 0.065* | |
H18B | 0.7113 | 0.4950 | 0.9821 | 0.065* | |
C19 | 0.75647 (19) | 0.46287 (16) | 0.70911 (13) | 0.0349 (4) | |
C20 | 0.7048 (2) | 0.55814 (18) | 0.75406 (15) | 0.0430 (4) | |
H20 | 0.5939 | 0.5279 | 0.7390 | 0.052* | |
C21 | 0.9210 (2) | 0.50904 (18) | 0.72988 (15) | 0.0421 (4) | |
H21 | 0.9561 | 0.4454 | 0.6982 | 0.051* | |
C22 | 0.8193 (2) | 0.69938 (19) | 0.82196 (16) | 0.0498 (5) | |
H22 | 0.7841 | 0.7632 | 0.8529 | 0.060* | |
C23 | 1.0333 (2) | 0.65013 (19) | 0.79784 (16) | 0.0475 (5) | |
H23 | 1.1442 | 0.6803 | 0.8124 | 0.057* | |
C24 | 0.9847 (2) | 0.74749 (18) | 0.84467 (15) | 0.0470 (5) | |
C25 | 1.1085 (3) | 0.9026 (2) | 0.9157 (2) | 0.0749 (7) | |
H25A | 1.1139 | 0.9249 | 0.9963 | 0.112* | |
H25B | 1.0762 | 0.9618 | 0.8850 | 0.112* | |
H25C | 1.2139 | 0.9195 | 0.9111 | 0.112* | |
N1 | 0.27694 (18) | 0.00144 (15) | 0.23907 (12) | 0.0431 (4) | |
N2 | 0.39960 (16) | 0.10481 (13) | 0.60410 (11) | 0.0333 (3) | |
N3 | 0.63721 (15) | 0.31543 (13) | 0.63513 (11) | 0.0349 (3) | |
N4 | 0.55969 (16) | 0.26207 (14) | 0.79310 (11) | 0.0389 (3) | |
O1 | 0.72370 (16) | 0.35460 (13) | 0.48475 (11) | 0.0592 (4) | |
O2 | 0.60257 (17) | 0.34084 (15) | 1.03546 (10) | 0.0618 (4) | |
S1 | −0.01771 (6) | −0.21021 (5) | 0.20492 (4) | 0.04755 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0365 (9) | 0.0324 (9) | 0.0348 (9) | 0.0125 (7) | 0.0084 (7) | 0.0108 (7) |
C2 | 0.0345 (9) | 0.0398 (10) | 0.0463 (11) | 0.0103 (8) | 0.0064 (8) | 0.0132 (8) |
C3 | 0.0354 (15) | 0.0420 (17) | 0.0527 (16) | 0.0125 (12) | 0.0148 (12) | 0.0195 (13) |
C4 | 0.0420 (15) | 0.0425 (15) | 0.0434 (14) | 0.0123 (12) | 0.0125 (12) | 0.0207 (13) |
C3' | 0.055 (7) | 0.060 (7) | 0.073 (7) | 0.028 (5) | 0.025 (6) | 0.038 (6) |
C4' | 0.048 (6) | 0.056 (6) | 0.057 (6) | 0.026 (5) | 0.026 (5) | 0.027 (5) |
C5 | 0.0412 (10) | 0.0384 (10) | 0.0352 (9) | 0.0111 (8) | 0.0096 (8) | 0.0134 (8) |
C6 | 0.0346 (9) | 0.0274 (8) | 0.0328 (9) | 0.0124 (7) | 0.0073 (7) | 0.0088 (7) |
C7 | 0.0356 (9) | 0.0264 (8) | 0.0302 (8) | 0.0130 (7) | 0.0083 (7) | 0.0081 (7) |
C8 | 0.0382 (9) | 0.0325 (9) | 0.0307 (9) | 0.0114 (8) | 0.0072 (7) | 0.0069 (7) |
C9 | 0.0433 (10) | 0.0353 (9) | 0.0339 (9) | 0.0166 (8) | 0.0151 (8) | 0.0133 (7) |
C10 | 0.0582 (13) | 0.0532 (12) | 0.0377 (10) | 0.0131 (10) | 0.0189 (9) | 0.0175 (9) |
C11 | 0.0360 (9) | 0.0290 (8) | 0.0323 (9) | 0.0140 (7) | 0.0117 (7) | 0.0101 (7) |
C12 | 0.0356 (9) | 0.0259 (8) | 0.0306 (9) | 0.0142 (7) | 0.0099 (7) | 0.0093 (7) |
C13 | 0.0388 (10) | 0.0322 (9) | 0.0374 (9) | 0.0131 (8) | 0.0136 (8) | 0.0118 (7) |
C14 | 0.0320 (9) | 0.0290 (8) | 0.0327 (9) | 0.0129 (7) | 0.0096 (7) | 0.0099 (7) |
C15 | 0.0432 (10) | 0.0401 (10) | 0.0348 (10) | 0.0067 (8) | 0.0118 (8) | 0.0089 (8) |
C16 | 0.0535 (12) | 0.0621 (13) | 0.0365 (10) | 0.0178 (10) | 0.0163 (9) | 0.0100 (9) |
C17 | 0.0392 (10) | 0.0428 (10) | 0.0381 (10) | 0.0133 (8) | 0.0058 (8) | 0.0166 (8) |
C18 | 0.0516 (12) | 0.0460 (11) | 0.0359 (10) | 0.0109 (9) | −0.0005 (9) | 0.0064 (9) |
C19 | 0.0318 (9) | 0.0286 (8) | 0.0325 (9) | 0.0074 (7) | 0.0060 (7) | 0.0094 (7) |
C20 | 0.0364 (10) | 0.0396 (10) | 0.0456 (10) | 0.0143 (8) | 0.0134 (8) | 0.0122 (8) |
C21 | 0.0357 (10) | 0.0399 (10) | 0.0466 (10) | 0.0148 (8) | 0.0124 (8) | 0.0170 (8) |
C22 | 0.0590 (12) | 0.0349 (10) | 0.0475 (11) | 0.0179 (9) | 0.0217 (10) | 0.0091 (8) |
C23 | 0.0318 (9) | 0.0456 (11) | 0.0457 (11) | 0.0042 (8) | 0.0035 (8) | 0.0196 (9) |
C24 | 0.0506 (11) | 0.0353 (10) | 0.0327 (9) | 0.0050 (9) | 0.0088 (8) | 0.0100 (8) |
C25 | 0.0724 (15) | 0.0394 (12) | 0.0637 (14) | −0.0032 (11) | 0.0123 (12) | 0.0050 (10) |
N1 | 0.0474 (9) | 0.0403 (8) | 0.0304 (8) | 0.0129 (7) | 0.0117 (7) | 0.0116 (6) |
N2 | 0.0341 (7) | 0.0277 (7) | 0.0287 (7) | 0.0096 (6) | 0.0075 (6) | 0.0079 (6) |
N3 | 0.0321 (7) | 0.0286 (7) | 0.0322 (7) | 0.0076 (6) | 0.0087 (6) | 0.0075 (6) |
N4 | 0.0333 (8) | 0.0364 (8) | 0.0275 (7) | 0.0051 (6) | 0.0056 (6) | 0.0063 (6) |
O1 | 0.0526 (8) | 0.0499 (8) | 0.0443 (8) | −0.0020 (7) | 0.0201 (7) | 0.0140 (6) |
O2 | 0.0605 (9) | 0.0700 (9) | 0.0291 (7) | 0.0157 (8) | 0.0100 (7) | 0.0105 (7) |
S1 | 0.0426 (3) | 0.0447 (3) | 0.0305 (2) | 0.0071 (2) | 0.0034 (2) | 0.0074 (2) |
C1—C6 | 1.355 (2) | C11—C12 | 1.404 (2) |
C1—C2 | 1.502 (2) | C11—C13 | 1.456 (2) |
C1—S1 | 1.7444 (17) | C12—N2 | 1.3698 (19) |
C2—C3' | 1.510 (8) | C13—O1 | 1.2126 (19) |
C2—C3 | 1.517 (3) | C13—N3 | 1.418 (2) |
C2—H2A | 0.9700 | C14—N2 | 1.3017 (19) |
C2—H2B | 0.9700 | C14—N4 | 1.369 (2) |
C2—H2C | 0.9700 | C14—N3 | 1.390 (2) |
C2—H2D | 0.9700 | C15—N4 | 1.457 (2) |
C3—C4 | 1.509 (4) | C15—C16 | 1.509 (2) |
C3—H3A | 0.9700 | C15—H15A | 0.9700 |
C3—H3B | 0.9700 | C15—H15B | 0.9700 |
C4—C5 | 1.531 (3) | C16—O2 | 1.417 (2) |
C4—H4A | 0.9700 | C16—H16A | 0.9700 |
C4—H4B | 0.9700 | C16—H16B | 0.9700 |
C3'—C4' | 1.506 (9) | C17—N4 | 1.469 (2) |
C3'—H3C | 0.9700 | C17—C18 | 1.506 (2) |
C3'—H3D | 0.9700 | C17—H17A | 0.9700 |
C4'—C5 | 1.523 (7) | C17—H17B | 0.9700 |
C4'—H4C | 0.9700 | C18—O2 | 1.415 (2) |
C4'—H4D | 0.9700 | C18—H18A | 0.9700 |
C5—C6 | 1.506 (2) | C18—H18B | 0.9700 |
C5—H5A | 0.9700 | C19—C20 | 1.376 (2) |
C5—H5B | 0.9700 | C19—C21 | 1.380 (2) |
C5—H5C | 0.9700 | C19—N3 | 1.4526 (19) |
C5—H5D | 0.9700 | C20—C22 | 1.385 (2) |
C6—C7 | 1.443 (2) | C20—H20 | 0.9300 |
C7—C8 | 1.395 (2) | C21—C23 | 1.380 (2) |
C7—C12 | 1.417 (2) | C21—H21 | 0.9300 |
C8—N1 | 1.348 (2) | C22—C24 | 1.381 (3) |
C8—S1 | 1.7302 (17) | C22—H22 | 0.9300 |
C9—N1 | 1.330 (2) | C23—C24 | 1.381 (3) |
C9—C11 | 1.424 (2) | C23—H23 | 0.9300 |
C9—C10 | 1.503 (2) | C24—C25 | 1.510 (2) |
C10—H10A | 0.9600 | C25—H25A | 0.9600 |
C10—H10B | 0.9600 | C25—H25B | 0.9600 |
C10—H10C | 0.9600 | C25—H25C | 0.9600 |
C6—C1—C2 | 126.12 (15) | N1—C9—C10 | 114.75 (14) |
C6—C1—S1 | 113.16 (13) | C11—C9—C10 | 123.62 (15) |
C2—C1—S1 | 120.70 (12) | C9—C10—H10A | 109.5 |
C1—C2—C3' | 108.2 (6) | C9—C10—H10B | 109.5 |
C1—C2—C3 | 110.51 (17) | H10A—C10—H10B | 109.5 |
C3'—C2—C3 | 26.5 (5) | C9—C10—H10C | 109.5 |
C1—C2—H2A | 109.5 | H10A—C10—H10C | 109.5 |
C3'—C2—H2A | 86.6 | H10B—C10—H10C | 109.5 |
C3—C2—H2A | 109.5 | C12—C11—C9 | 120.69 (14) |
C1—C2—H2B | 109.5 | C12—C11—C13 | 117.87 (14) |
C3'—C2—H2B | 131.4 | C9—C11—C13 | 121.30 (14) |
C3—C2—H2B | 109.5 | N2—C12—C11 | 123.20 (14) |
H2A—C2—H2B | 108.1 | N2—C12—C7 | 119.02 (13) |
C1—C2—H2C | 110.7 | C11—C12—C7 | 117.77 (14) |
C3'—C2—H2C | 109.0 | O1—C13—N3 | 119.07 (15) |
C3—C2—H2C | 127.8 | O1—C13—C11 | 125.76 (16) |
H2A—C2—H2C | 24.9 | N3—C13—C11 | 115.04 (14) |
H2B—C2—H2C | 84.9 | N2—C14—N4 | 118.31 (14) |
C1—C2—H2D | 109.7 | N2—C14—N3 | 123.00 (14) |
C3'—C2—H2D | 110.8 | N4—C14—N3 | 118.61 (13) |
C3—C2—H2D | 85.8 | N4—C15—C16 | 108.66 (14) |
H2A—C2—H2D | 128.6 | N4—C15—H15A | 110.0 |
H2B—C2—H2D | 26.2 | C16—C15—H15A | 110.0 |
H2C—C2—H2D | 108.4 | N4—C15—H15B | 110.0 |
C4—C3—C2 | 111.5 (2) | C16—C15—H15B | 110.0 |
C4—C3—H3A | 109.3 | H15A—C15—H15B | 108.3 |
C2—C3—H3A | 109.3 | O2—C16—C15 | 112.79 (16) |
C4—C3—H3B | 109.3 | O2—C16—H16A | 109.0 |
C2—C3—H3B | 109.3 | C15—C16—H16A | 109.0 |
H3A—C3—H3B | 108.0 | O2—C16—H16B | 109.0 |
C3—C4—C5 | 111.9 (2) | C15—C16—H16B | 109.0 |
C3—C4—H4A | 109.2 | H16A—C16—H16B | 107.8 |
C5—C4—H4A | 109.2 | N4—C17—C18 | 108.47 (15) |
C3—C4—H4B | 109.2 | N4—C17—H17A | 110.0 |
C5—C4—H4B | 109.2 | C18—C17—H17A | 110.0 |
H4A—C4—H4B | 107.9 | N4—C17—H17B | 110.0 |
C4'—C3'—C2 | 113.3 (9) | C18—C17—H17B | 110.0 |
C4'—C3'—H3C | 108.9 | H17A—C17—H17B | 108.4 |
C2—C3'—H3C | 108.9 | O2—C18—C17 | 111.31 (15) |
C4'—C3'—H3D | 108.9 | O2—C18—H18A | 109.4 |
C2—C3'—H3D | 108.9 | C17—C18—H18A | 109.4 |
H3C—C3'—H3D | 107.7 | O2—C18—H18B | 109.4 |
C3'—C4'—C5 | 109.5 (10) | C17—C18—H18B | 109.4 |
C3'—C4'—H4C | 109.8 | H18A—C18—H18B | 108.0 |
C5—C4'—H4C | 109.8 | C20—C19—C21 | 119.94 (15) |
C3'—C4'—H4D | 109.8 | C20—C19—N3 | 119.94 (14) |
C5—C4'—H4D | 109.8 | C21—C19—N3 | 120.05 (15) |
H4C—C4'—H4D | 108.2 | C19—C20—C22 | 119.51 (17) |
C6—C5—C4' | 112.2 (5) | C19—C20—H20 | 120.2 |
C6—C5—C4 | 110.86 (16) | C22—C20—H20 | 120.2 |
C4'—C5—C4 | 30.2 (5) | C19—C21—C23 | 119.72 (17) |
C6—C5—H5A | 109.5 | C19—C21—H21 | 120.1 |
C4'—C5—H5A | 81.3 | C23—C21—H21 | 120.1 |
C4—C5—H5A | 109.5 | C24—C22—C20 | 121.45 (18) |
C6—C5—H5B | 109.5 | C24—C22—H22 | 119.3 |
C4'—C5—H5B | 130.9 | C20—C22—H22 | 119.3 |
C4—C5—H5B | 109.5 | C21—C23—C24 | 121.42 (17) |
H5A—C5—H5B | 108.1 | C21—C23—H23 | 119.3 |
C6—C5—H5C | 109.3 | C24—C23—H23 | 119.3 |
C4'—C5—H5C | 111.1 | C23—C24—C22 | 117.94 (16) |
C4—C5—H5C | 133.6 | C23—C24—C25 | 120.88 (19) |
H5A—C5—H5C | 33.2 | C22—C24—C25 | 121.16 (19) |
H5B—C5—H5C | 77.4 | C24—C25—H25A | 109.5 |
C6—C5—H5D | 110.5 | C24—C25—H25B | 109.5 |
C4'—C5—H5D | 105.6 | H25A—C25—H25B | 109.5 |
C4—C5—H5D | 78.4 | C24—C25—H25C | 109.5 |
H5A—C5—H5D | 132.7 | H25A—C25—H25C | 109.5 |
H5B—C5—H5D | 33.7 | H25B—C25—H25C | 109.5 |
H5C—C5—H5D | 108.2 | C9—N1—C8 | 116.59 (14) |
C1—C6—C7 | 111.94 (14) | C14—N2—C12 | 118.60 (13) |
C1—C6—C5 | 120.97 (14) | C14—N3—C13 | 121.20 (13) |
C7—C6—C5 | 127.09 (14) | C14—N3—C19 | 123.13 (13) |
C8—C7—C12 | 115.84 (14) | C13—N3—C19 | 115.03 (13) |
C8—C7—C6 | 112.20 (14) | C14—N4—C15 | 118.26 (13) |
C12—C7—C6 | 131.92 (14) | C14—N4—C17 | 124.57 (13) |
N1—C8—C7 | 127.40 (15) | C15—N4—C17 | 110.14 (13) |
N1—C8—S1 | 120.85 (12) | C18—O2—C16 | 110.07 (13) |
C7—C8—S1 | 111.75 (12) | C8—S1—C1 | 90.93 (8) |
N1—C9—C11 | 121.62 (15) | ||
C6—C1—C2—C3' | −14.6 (6) | N4—C15—C16—O2 | −56.6 (2) |
S1—C1—C2—C3' | 164.0 (6) | N4—C17—C18—O2 | 59.66 (19) |
C6—C1—C2—C3 | 13.4 (3) | C21—C19—C20—C22 | −1.3 (3) |
S1—C1—C2—C3 | −168.07 (17) | N3—C19—C20—C22 | −178.31 (15) |
C1—C2—C3—C4 | −42.7 (3) | C20—C19—C21—C23 | 1.4 (2) |
C3'—C2—C3—C4 | 47.1 (12) | N3—C19—C21—C23 | 178.37 (14) |
C2—C3—C4—C5 | 62.4 (4) | C19—C20—C22—C24 | 0.7 (3) |
C1—C2—C3'—C4' | 47.1 (14) | C19—C21—C23—C24 | −0.9 (3) |
C3—C2—C3'—C4' | −52.6 (9) | C21—C23—C24—C22 | 0.3 (3) |
C2—C3'—C4'—C5 | −64.7 (18) | C21—C23—C24—C25 | −178.07 (17) |
C3'—C4'—C5—C6 | 45.2 (13) | C20—C22—C24—C23 | −0.2 (3) |
C3'—C4'—C5—C4 | −48.5 (8) | C20—C22—C24—C25 | 178.14 (17) |
C3—C4—C5—C6 | −47.9 (4) | C11—C9—N1—C8 | −1.5 (2) |
C3—C4—C5—C4' | 50.7 (9) | C10—C9—N1—C8 | 179.55 (15) |
C2—C1—C6—C7 | 178.67 (15) | C7—C8—N1—C9 | −1.4 (3) |
S1—C1—C6—C7 | 0.05 (19) | S1—C8—N1—C9 | 178.60 (13) |
C2—C1—C6—C5 | −1.1 (3) | N4—C14—N2—C12 | 174.22 (14) |
S1—C1—C6—C5 | −179.76 (12) | N3—C14—N2—C12 | −2.3 (2) |
C4'—C5—C6—C1 | −14.5 (6) | C11—C12—N2—C14 | 8.5 (2) |
C4—C5—C6—C1 | 18.0 (3) | C7—C12—N2—C14 | −171.09 (14) |
C4'—C5—C6—C7 | 165.7 (6) | N2—C14—N3—C13 | −7.5 (2) |
C4—C5—C6—C7 | −161.8 (2) | N4—C14—N3—C13 | 175.91 (14) |
C1—C6—C7—C8 | −0.7 (2) | N2—C14—N3—C19 | 162.82 (15) |
C5—C6—C7—C8 | 179.15 (15) | N4—C14—N3—C19 | −13.7 (2) |
C1—C6—C7—C12 | 176.86 (16) | O1—C13—N3—C14 | −173.20 (15) |
C5—C6—C7—C12 | −3.3 (3) | C11—C13—N3—C14 | 10.7 (2) |
C12—C7—C8—N1 | 3.0 (3) | O1—C13—N3—C19 | 15.7 (2) |
C6—C7—C8—N1 | −179.08 (16) | C11—C13—N3—C19 | −160.42 (14) |
C12—C7—C8—S1 | −176.99 (11) | C20—C19—N3—C14 | −63.1 (2) |
C6—C7—C8—S1 | 0.96 (18) | C21—C19—N3—C14 | 119.86 (17) |
N1—C9—C11—C12 | 2.5 (2) | C20—C19—N3—C13 | 107.76 (17) |
C10—C9—C11—C12 | −178.59 (16) | C21—C19—N3—C13 | −69.23 (19) |
N1—C9—C11—C13 | −173.04 (15) | N2—C14—N4—C15 | −9.5 (2) |
C10—C9—C11—C13 | 5.8 (3) | N3—C14—N4—C15 | 167.24 (14) |
C9—C11—C12—N2 | 179.64 (15) | N2—C14—N4—C17 | 138.21 (16) |
C13—C11—C12—N2 | −4.6 (2) | N3—C14—N4—C17 | −45.1 (2) |
C9—C11—C12—C7 | −0.8 (2) | C16—C15—N4—C14 | −150.84 (16) |
C13—C11—C12—C7 | 174.94 (14) | C16—C15—N4—C17 | 57.13 (19) |
C8—C7—C12—N2 | 177.90 (14) | C18—C17—N4—C14 | 151.08 (15) |
C6—C7—C12—N2 | 0.5 (3) | C18—C17—N4—C15 | −59.03 (18) |
C8—C7—C12—C11 | −1.7 (2) | C17—C18—O2—C16 | −58.5 (2) |
C6—C7—C12—C11 | −179.14 (15) | C15—C16—O2—C18 | 57.3 (2) |
C12—C11—C13—O1 | 179.39 (16) | N1—C8—S1—C1 | 179.25 (15) |
C9—C11—C13—O1 | −4.9 (3) | C7—C8—S1—C1 | −0.78 (13) |
C12—C11—C13—N3 | −4.8 (2) | C6—C1—S1—C8 | 0.42 (14) |
C9—C11—C13—N3 | 170.91 (14) | C2—C1—S1—C8 | −178.29 (14) |