Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022847/ez2005sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022847/ez2005Isup2.hkl |
CCDC reference: 614862
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.
C30H22N4O2S | Dx = 1.358 Mg m−3 |
Mr = 502.58 | Melting point = 507–508 K |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 4130 reflections |
a = 16.126 (4) Å | θ = 2.5–23.4° |
b = 12.852 (4) Å | µ = 0.17 mm−1 |
c = 23.725 (6) Å | T = 294 K |
V = 4917 (2) Å3 | Block, colorless |
Z = 8 | 0.24 × 0.20 × 0.10 mm |
F(000) = 2096 |
Bruker APEX CCD area-detector diffractometer | 4331 independent reflections |
Radiation source: fine-focus sealed tube | 2725 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
φ and ω scans | θmax = 25.0°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −19→18 |
Tmin = 0.961, Tmax = 0.983 | k = −14→15 |
24035 measured reflections | l = −28→15 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.0527P)2 + 0.4279P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.114 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.26 e Å−3 |
4331 reflections | Δρmin = −0.23 e Å−3 |
335 parameters |
Experimental. 1H NMR (CDCl3): δ 2.39 (s, 3H), 3.74–3.78 (m, 1H), 4.50–4.54 (m, 1H), 5.55–5.58 (m, 1H), 6.71–8.18 (m, 15H), 7.95 (br, 1H). |
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 | 0.13697 (4) | 0.42321 (5) | 0.42196 (3) | 0.03489 (19) | |
O1 | 0.15909 (11) | 0.12191 (13) | 0.42720 (7) | 0.0392 (4) | |
O2 | −0.01590 (11) | 0.45329 (14) | 0.34229 (8) | 0.0490 (5) | |
N1 | 0.15465 (12) | 0.26136 (15) | 0.48821 (8) | 0.0307 (5) | |
N2 | 0.16455 (12) | 0.41174 (16) | 0.53771 (8) | 0.0351 (5) | |
N3 | 0.01424 (12) | 0.21643 (16) | 0.32914 (8) | 0.0337 (5) | |
N4 | −0.07907 (13) | 0.39396 (16) | 0.42392 (9) | 0.0398 (5) | |
H4 | −0.1060 | 0.4493 | 0.4328 | 0.048* | |
C1 | 0.11363 (14) | 0.29286 (17) | 0.39178 (9) | 0.0280 (6) | |
C2 | 0.15124 (14) | 0.36978 (19) | 0.48854 (10) | 0.0305 (6) | |
C3 | 0.14511 (14) | 0.21324 (19) | 0.43609 (9) | 0.0281 (6) | |
C4 | 0.17426 (14) | 0.23060 (19) | 0.54378 (10) | 0.0313 (6) | |
C5 | 0.18804 (16) | 0.1344 (2) | 0.56867 (11) | 0.0416 (7) | |
H5 | 0.1844 | 0.0727 | 0.5484 | 0.050* | |
C6 | 0.20773 (17) | 0.1359 (2) | 0.62585 (11) | 0.0479 (7) | |
H6 | 0.2176 | 0.0733 | 0.6443 | 0.058* | |
C7 | 0.21302 (17) | 0.2291 (2) | 0.65634 (11) | 0.0474 (7) | |
H7 | 0.2266 | 0.2269 | 0.6944 | 0.057* | |
C8 | 0.19848 (16) | 0.3242 (2) | 0.63095 (10) | 0.0435 (7) | |
H8 | 0.2014 | 0.3858 | 0.6515 | 0.052* | |
C9 | 0.17942 (15) | 0.3252 (2) | 0.57382 (10) | 0.0336 (6) | |
C10 | 0.01559 (14) | 0.27636 (19) | 0.38159 (10) | 0.0299 (6) | |
C11 | −0.03178 (15) | 0.22573 (19) | 0.42941 (10) | 0.0316 (6) | |
C12 | −0.03402 (16) | 0.1236 (2) | 0.44783 (11) | 0.0394 (7) | |
H12 | −0.0026 | 0.0726 | 0.4300 | 0.047* | |
C13 | −0.08448 (17) | 0.0985 (2) | 0.49389 (11) | 0.0457 (7) | |
H13 | −0.0861 | 0.0305 | 0.5072 | 0.055* | |
C14 | −0.13203 (17) | 0.1746 (2) | 0.51964 (11) | 0.0475 (8) | |
H14 | −0.1643 | 0.1570 | 0.5507 | 0.057* | |
C15 | −0.13275 (16) | 0.2763 (2) | 0.50043 (11) | 0.0435 (7) | |
H15 | −0.1653 | 0.3268 | 0.5178 | 0.052* | |
C16 | −0.08341 (15) | 0.3001 (2) | 0.45458 (10) | 0.0338 (6) | |
C17 | −0.02748 (15) | 0.3870 (2) | 0.37866 (11) | 0.0353 (6) | |
C18 | −0.06814 (17) | 0.2024 (2) | 0.30378 (11) | 0.0523 (8) | |
H18A | −0.1043 | 0.1695 | 0.3305 | 0.078* | |
H18B | −0.0635 | 0.1596 | 0.2708 | 0.078* | |
H18C | −0.0904 | 0.2690 | 0.2935 | 0.078* | |
C19 | 0.07723 (15) | 0.2629 (2) | 0.29241 (10) | 0.0367 (6) | |
H19A | 0.0599 | 0.3307 | 0.2789 | 0.044* | |
H19B | 0.0893 | 0.2184 | 0.2604 | 0.044* | |
C20 | 0.15213 (14) | 0.27153 (19) | 0.33192 (9) | 0.0289 (6) | |
H20 | 0.1773 | 0.2022 | 0.3336 | 0.035* | |
C21 | 0.22052 (15) | 0.34639 (19) | 0.31388 (9) | 0.0319 (6) | |
C22 | 0.20157 (17) | 0.4403 (2) | 0.28917 (10) | 0.0409 (7) | |
H22 | 0.1462 | 0.4569 | 0.2828 | 0.049* | |
C23 | 0.2634 (2) | 0.5125 (2) | 0.27313 (11) | 0.0519 (8) | |
H23 | 0.2487 | 0.5742 | 0.2553 | 0.062* | |
C24 | 0.3451 (2) | 0.4911 (2) | 0.28397 (12) | 0.0567 (9) | |
H24 | 0.3856 | 0.5390 | 0.2737 | 0.068* | |
C25 | 0.36869 (17) | 0.3968 (2) | 0.31060 (11) | 0.0439 (7) | |
C26 | 0.45345 (19) | 0.3747 (3) | 0.32402 (13) | 0.0600 (9) | |
H26 | 0.4936 | 0.4251 | 0.3171 | 0.072* | |
C27 | 0.4768 (2) | 0.2824 (3) | 0.34655 (14) | 0.0627 (9) | |
H27 | 0.5322 | 0.2699 | 0.3550 | 0.075* | |
C28 | 0.41689 (18) | 0.2057 (3) | 0.35702 (11) | 0.0523 (8) | |
H28 | 0.4333 | 0.1413 | 0.3711 | 0.063* | |
C29 | 0.33432 (16) | 0.2242 (2) | 0.34683 (10) | 0.0399 (7) | |
H29 | 0.2957 | 0.1725 | 0.3548 | 0.048* | |
C30 | 0.30673 (15) | 0.3212 (2) | 0.32420 (9) | 0.0349 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0468 (4) | 0.0273 (4) | 0.0306 (3) | −0.0002 (3) | −0.0043 (3) | 0.0011 (3) |
O1 | 0.0518 (12) | 0.0275 (11) | 0.0382 (10) | 0.0076 (8) | −0.0016 (8) | −0.0018 (8) |
O2 | 0.0551 (13) | 0.0420 (12) | 0.0500 (12) | 0.0082 (9) | −0.0013 (9) | 0.0158 (10) |
N1 | 0.0366 (12) | 0.0279 (12) | 0.0276 (11) | 0.0022 (9) | −0.0040 (9) | 0.0003 (9) |
N2 | 0.0408 (13) | 0.0352 (13) | 0.0291 (11) | 0.0030 (10) | −0.0030 (9) | −0.0041 (10) |
N3 | 0.0296 (12) | 0.0405 (14) | 0.0311 (12) | −0.0022 (10) | −0.0011 (9) | −0.0019 (10) |
N4 | 0.0385 (14) | 0.0336 (13) | 0.0472 (13) | 0.0098 (10) | 0.0080 (11) | −0.0023 (11) |
C1 | 0.0324 (14) | 0.0258 (14) | 0.0258 (13) | 0.0013 (11) | −0.0001 (10) | −0.0012 (10) |
C2 | 0.0283 (14) | 0.0296 (15) | 0.0335 (14) | 0.0030 (11) | −0.0002 (11) | 0.0001 (11) |
C3 | 0.0250 (13) | 0.0298 (15) | 0.0295 (14) | 0.0014 (11) | −0.0006 (10) | −0.0003 (11) |
C4 | 0.0288 (14) | 0.0366 (16) | 0.0285 (14) | 0.0045 (12) | −0.0011 (11) | 0.0047 (12) |
C5 | 0.0459 (17) | 0.0390 (17) | 0.0399 (16) | 0.0022 (13) | −0.0040 (13) | 0.0039 (13) |
C6 | 0.0506 (19) | 0.053 (2) | 0.0405 (17) | 0.0037 (15) | −0.0064 (13) | 0.0139 (14) |
C7 | 0.0451 (18) | 0.070 (2) | 0.0272 (15) | −0.0026 (15) | −0.0040 (12) | 0.0058 (15) |
C8 | 0.0501 (18) | 0.0520 (19) | 0.0286 (14) | −0.0064 (14) | −0.0046 (12) | −0.0052 (13) |
C9 | 0.0325 (15) | 0.0392 (16) | 0.0289 (14) | 0.0002 (12) | 0.0002 (11) | −0.0006 (12) |
C10 | 0.0296 (14) | 0.0318 (15) | 0.0282 (14) | 0.0040 (11) | 0.0000 (10) | 0.0045 (11) |
C11 | 0.0280 (14) | 0.0355 (15) | 0.0313 (14) | 0.0014 (11) | 0.0002 (11) | 0.0015 (11) |
C12 | 0.0385 (16) | 0.0366 (17) | 0.0430 (16) | −0.0019 (13) | −0.0024 (13) | 0.0033 (13) |
C13 | 0.0469 (18) | 0.0447 (19) | 0.0455 (17) | −0.0131 (15) | −0.0046 (14) | 0.0120 (14) |
C14 | 0.0374 (17) | 0.069 (2) | 0.0359 (16) | −0.0127 (16) | 0.0018 (13) | 0.0053 (15) |
C15 | 0.0371 (16) | 0.056 (2) | 0.0373 (15) | 0.0009 (14) | 0.0056 (12) | −0.0039 (14) |
C16 | 0.0270 (14) | 0.0394 (17) | 0.0350 (15) | 0.0003 (12) | −0.0015 (11) | −0.0010 (12) |
C17 | 0.0303 (15) | 0.0349 (16) | 0.0409 (16) | 0.0035 (12) | −0.0056 (12) | 0.0018 (13) |
C18 | 0.0387 (17) | 0.075 (2) | 0.0435 (17) | −0.0123 (15) | −0.0077 (13) | −0.0013 (15) |
C19 | 0.0366 (16) | 0.0448 (17) | 0.0286 (14) | −0.0026 (12) | −0.0009 (11) | −0.0013 (12) |
C20 | 0.0269 (13) | 0.0327 (15) | 0.0270 (13) | 0.0024 (11) | 0.0003 (11) | −0.0018 (11) |
C21 | 0.0381 (16) | 0.0338 (16) | 0.0239 (13) | −0.0001 (12) | 0.0059 (11) | −0.0034 (11) |
C22 | 0.0460 (17) | 0.0426 (18) | 0.0341 (15) | 0.0015 (14) | 0.0050 (12) | −0.0004 (13) |
C23 | 0.075 (2) | 0.0341 (17) | 0.0461 (18) | −0.0023 (16) | 0.0173 (15) | 0.0021 (13) |
C24 | 0.065 (2) | 0.045 (2) | 0.061 (2) | −0.0168 (17) | 0.0288 (16) | −0.0103 (15) |
C25 | 0.0429 (18) | 0.0461 (19) | 0.0429 (16) | −0.0101 (14) | 0.0139 (13) | −0.0106 (13) |
C26 | 0.038 (2) | 0.076 (3) | 0.066 (2) | −0.0190 (17) | 0.0154 (15) | −0.0191 (18) |
C27 | 0.0361 (19) | 0.087 (3) | 0.065 (2) | 0.0048 (19) | 0.0015 (15) | −0.013 (2) |
C28 | 0.0408 (19) | 0.066 (2) | 0.0501 (19) | 0.0058 (16) | 0.0021 (14) | −0.0016 (15) |
C29 | 0.0353 (17) | 0.0490 (18) | 0.0352 (15) | −0.0012 (13) | 0.0022 (12) | −0.0039 (13) |
C30 | 0.0391 (16) | 0.0429 (17) | 0.0227 (13) | −0.0034 (13) | 0.0065 (11) | −0.0061 (11) |
S1—C2 | 1.738 (2) | C12—H12 | 0.9300 |
S1—C1 | 1.860 (2) | C13—C14 | 1.385 (4) |
O1—C3 | 1.214 (3) | C13—H13 | 0.9300 |
O2—C17 | 1.227 (3) | C14—C15 | 1.384 (4) |
N1—C3 | 1.391 (3) | C14—H14 | 0.9300 |
N1—C2 | 1.395 (3) | C15—C16 | 1.382 (3) |
N1—C4 | 1.412 (3) | C15—H15 | 0.9300 |
N2—C2 | 1.303 (3) | C18—H18A | 0.9600 |
N2—C9 | 1.424 (3) | C18—H18B | 0.9600 |
N3—C10 | 1.464 (3) | C18—H18C | 0.9600 |
N3—C19 | 1.466 (3) | C19—C20 | 1.533 (3) |
N3—C18 | 1.470 (3) | C19—H19A | 0.9700 |
N4—C17 | 1.361 (3) | C19—H19B | 0.9700 |
N4—C16 | 1.410 (3) | C20—C21 | 1.525 (3) |
N4—H4 | 0.8600 | C20—H20 | 0.9800 |
C1—C3 | 1.552 (3) | C21—C22 | 1.376 (3) |
C1—C20 | 1.574 (3) | C21—C30 | 1.448 (3) |
C1—C10 | 1.613 (3) | C22—C23 | 1.414 (4) |
C4—C5 | 1.388 (3) | C22—H22 | 0.9300 |
C4—C9 | 1.412 (3) | C23—C24 | 1.370 (4) |
C5—C6 | 1.393 (3) | C23—H23 | 0.9300 |
C5—H5 | 0.9300 | C24—C25 | 1.418 (4) |
C6—C7 | 1.402 (4) | C24—H24 | 0.9300 |
C6—H6 | 0.9300 | C25—C30 | 1.431 (4) |
C7—C8 | 1.383 (4) | C25—C26 | 1.432 (4) |
C7—H7 | 0.9300 | C26—C27 | 1.355 (4) |
C8—C9 | 1.390 (3) | C26—H26 | 0.9300 |
C8—H8 | 0.9300 | C27—C28 | 1.402 (4) |
C10—C11 | 1.515 (3) | C27—H27 | 0.9300 |
C10—C17 | 1.584 (3) | C28—C29 | 1.374 (4) |
C11—C12 | 1.384 (3) | C28—H28 | 0.9300 |
C11—C16 | 1.401 (3) | C29—C30 | 1.429 (4) |
C12—C13 | 1.400 (3) | C29—H29 | 0.9300 |
C2—S1—C1 | 91.19 (11) | C13—C14—H14 | 119.1 |
C3—N1—C2 | 116.42 (19) | C16—C15—C14 | 117.6 (3) |
C3—N1—C4 | 136.9 (2) | C16—C15—H15 | 121.2 |
C2—N1—C4 | 106.45 (19) | C14—C15—H15 | 121.2 |
C2—N2—C9 | 104.1 (2) | C15—C16—C11 | 121.8 (2) |
C10—N3—C19 | 106.32 (19) | C15—C16—N4 | 128.6 (2) |
C10—N3—C18 | 115.2 (2) | C11—C16—N4 | 109.5 (2) |
C19—N3—C18 | 115.65 (19) | O2—C17—N4 | 127.0 (2) |
C17—N4—C16 | 112.4 (2) | O2—C17—C10 | 126.0 (2) |
C17—N4—H4 | 123.8 | N4—C17—C10 | 107.0 (2) |
C16—N4—H4 | 123.8 | N3—C18—H18A | 109.5 |
C3—C1—C20 | 111.55 (19) | N3—C18—H18B | 109.5 |
C3—C1—C10 | 109.58 (18) | H18A—C18—H18B | 109.5 |
C20—C1—C10 | 103.21 (17) | N3—C18—H18C | 109.5 |
C3—C1—S1 | 105.48 (15) | H18A—C18—H18C | 109.5 |
C20—C1—S1 | 115.10 (16) | H18B—C18—H18C | 109.5 |
C10—C1—S1 | 111.98 (15) | N3—C19—C20 | 102.24 (18) |
N2—C2—N1 | 114.3 (2) | N3—C19—H19A | 111.3 |
N2—C2—S1 | 132.2 (2) | C20—C19—H19A | 111.3 |
N1—C2—S1 | 113.26 (17) | N3—C19—H19B | 111.3 |
O1—C3—N1 | 124.3 (2) | C20—C19—H19B | 111.3 |
O1—C3—C1 | 125.5 (2) | H19A—C19—H19B | 109.2 |
N1—C3—C1 | 110.2 (2) | C21—C20—C19 | 116.37 (19) |
C5—C4—C9 | 122.9 (2) | C21—C20—C1 | 115.38 (18) |
C5—C4—N1 | 133.0 (2) | C19—C20—C1 | 104.69 (18) |
C9—C4—N1 | 104.1 (2) | C21—C20—H20 | 106.6 |
C4—C5—C6 | 116.0 (3) | C19—C20—H20 | 106.6 |
C4—C5—H5 | 122.0 | C1—C20—H20 | 106.6 |
C6—C5—H5 | 122.0 | C22—C21—C30 | 118.8 (2) |
C5—C6—C7 | 121.9 (3) | C22—C21—C20 | 120.8 (2) |
C5—C6—H6 | 119.1 | C30—C21—C20 | 120.4 (2) |
C7—C6—H6 | 119.1 | C21—C22—C23 | 122.2 (3) |
C8—C7—C6 | 121.4 (2) | C21—C22—H22 | 118.9 |
C8—C7—H7 | 119.3 | C23—C22—H22 | 118.9 |
C6—C7—H7 | 119.3 | C24—C23—C22 | 119.7 (3) |
C7—C8—C9 | 118.0 (3) | C24—C23—H23 | 120.1 |
C7—C8—H8 | 121.0 | C22—C23—H23 | 120.1 |
C9—C8—H8 | 121.0 | C23—C24—C25 | 120.9 (3) |
C8—C9—C4 | 119.9 (2) | C23—C24—H24 | 119.6 |
C8—C9—N2 | 129.1 (2) | C25—C24—H24 | 119.6 |
C4—C9—N2 | 111.0 (2) | C24—C25—C30 | 119.6 (3) |
N3—C10—C11 | 113.8 (2) | C24—C25—C26 | 121.6 (3) |
N3—C10—C17 | 115.38 (19) | C30—C25—C26 | 118.8 (3) |
C11—C10—C17 | 101.38 (19) | C27—C26—C25 | 121.7 (3) |
N3—C10—C1 | 102.19 (17) | C27—C26—H26 | 119.1 |
C11—C10—C1 | 116.01 (19) | C25—C26—H26 | 119.1 |
C17—C10—C1 | 108.55 (19) | C26—C27—C28 | 119.7 (3) |
C12—C11—C16 | 119.8 (2) | C26—C27—H27 | 120.2 |
C12—C11—C10 | 131.1 (2) | C28—C27—H27 | 120.2 |
C16—C11—C10 | 109.0 (2) | C29—C28—C27 | 121.0 (3) |
C11—C12—C13 | 118.7 (3) | C29—C28—H28 | 119.5 |
C11—C12—H12 | 120.7 | C27—C28—H28 | 119.5 |
C13—C12—H12 | 120.7 | C28—C29—C30 | 121.3 (3) |
C14—C13—C12 | 120.2 (3) | C28—C29—H29 | 119.4 |
C14—C13—H13 | 119.9 | C30—C29—H29 | 119.4 |
C12—C13—H13 | 119.9 | C29—C30—C25 | 117.4 (2) |
C15—C14—C13 | 121.8 (3) | C29—C30—C21 | 123.9 (2) |
C15—C14—H14 | 119.1 | C25—C30—C21 | 118.7 (2) |
C2—S1—C1—C3 | −16.28 (16) | C1—C10—C11—C16 | 109.7 (2) |
C2—S1—C1—C20 | −139.69 (17) | C16—C11—C12—C13 | −4.0 (4) |
C2—S1—C1—C10 | 102.85 (16) | C10—C11—C12—C13 | −179.9 (2) |
C9—N2—C2—N1 | 0.9 (3) | C11—C12—C13—C14 | 1.1 (4) |
C9—N2—C2—S1 | −174.0 (2) | C12—C13—C14—C15 | 1.3 (4) |
C3—N1—C2—N2 | −176.8 (2) | C13—C14—C15—C16 | −0.6 (4) |
C4—N1—C2—N2 | −1.4 (3) | C14—C15—C16—C11 | −2.4 (4) |
C3—N1—C2—S1 | −0.9 (3) | C14—C15—C16—N4 | 173.3 (2) |
C4—N1—C2—S1 | 174.49 (16) | C12—C11—C16—C15 | 4.8 (4) |
C1—S1—C2—N2 | −174.3 (2) | C10—C11—C16—C15 | −178.5 (2) |
C1—S1—C2—N1 | 10.81 (18) | C12—C11—C16—N4 | −171.7 (2) |
C2—N1—C3—O1 | 168.1 (2) | C10—C11—C16—N4 | 5.0 (3) |
C4—N1—C3—O1 | −5.4 (4) | C17—N4—C16—C15 | −175.7 (3) |
C2—N1—C3—C1 | −12.3 (3) | C17—N4—C16—C11 | 0.5 (3) |
C4—N1—C3—C1 | 174.1 (2) | C16—N4—C17—O2 | 174.5 (2) |
C20—C1—C3—O1 | −36.1 (3) | C16—N4—C17—C10 | −5.6 (3) |
C10—C1—C3—O1 | 77.5 (3) | N3—C10—C17—O2 | −48.7 (3) |
S1—C1—C3—O1 | −161.8 (2) | C11—C10—C17—O2 | −172.2 (2) |
C20—C1—C3—N1 | 144.31 (19) | C1—C10—C17—O2 | 65.2 (3) |
C10—C1—C3—N1 | −102.0 (2) | N3—C10—C17—N4 | 131.3 (2) |
S1—C1—C3—N1 | 18.7 (2) | C11—C10—C17—N4 | 7.9 (2) |
C3—N1—C4—C5 | −3.9 (5) | C1—C10—C17—N4 | −114.7 (2) |
C2—N1—C4—C5 | −177.9 (3) | C10—N3—C19—C20 | 47.9 (2) |
C3—N1—C4—C9 | 175.2 (3) | C18—N3—C19—C20 | 177.1 (2) |
C2—N1—C4—C9 | 1.2 (2) | N3—C19—C20—C21 | −161.64 (19) |
C9—C4—C5—C6 | −0.1 (4) | N3—C19—C20—C1 | −33.0 (2) |
N1—C4—C5—C6 | 178.9 (2) | C3—C1—C20—C21 | −104.6 (2) |
C4—C5—C6—C7 | 0.2 (4) | C10—C1—C20—C21 | 137.8 (2) |
C5—C6—C7—C8 | 0.3 (4) | S1—C1—C20—C21 | 15.5 (3) |
C6—C7—C8—C9 | −0.8 (4) | C3—C1—C20—C19 | 126.2 (2) |
C7—C8—C9—C4 | 0.9 (4) | C10—C1—C20—C19 | 8.6 (2) |
C7—C8—C9—N2 | −177.8 (2) | S1—C1—C20—C19 | −113.73 (18) |
C5—C4—C9—C8 | −0.5 (4) | C19—C20—C21—C22 | 38.8 (3) |
N1—C4—C9—C8 | −179.7 (2) | C1—C20—C21—C22 | −84.4 (3) |
C5—C4—C9—N2 | 178.5 (2) | C19—C20—C21—C30 | −143.2 (2) |
N1—C4—C9—N2 | −0.8 (3) | C1—C20—C21—C30 | 93.6 (3) |
C2—N2—C9—C8 | 178.8 (3) | C30—C21—C22—C23 | 0.5 (4) |
C2—N2—C9—C4 | 0.0 (3) | C20—C21—C22—C23 | 178.5 (2) |
C19—N3—C10—C11 | −167.30 (19) | C21—C22—C23—C24 | −2.3 (4) |
C18—N3—C10—C11 | 63.2 (3) | C22—C23—C24—C25 | 0.7 (4) |
C19—N3—C10—C17 | 76.1 (2) | C23—C24—C25—C30 | 2.6 (4) |
C18—N3—C10—C17 | −53.4 (3) | C23—C24—C25—C26 | −177.8 (3) |
C19—N3—C10—C1 | −41.5 (2) | C24—C25—C26—C27 | −176.2 (3) |
C18—N3—C10—C1 | −171.0 (2) | C30—C25—C26—C27 | 3.3 (4) |
C3—C1—C10—N3 | −100.2 (2) | C25—C26—C27—C28 | 0.2 (5) |
C20—C1—C10—N3 | 18.7 (2) | C26—C27—C28—C29 | −2.6 (4) |
S1—C1—C10—N3 | 143.12 (15) | C27—C28—C29—C30 | 1.3 (4) |
C3—C1—C10—C11 | 24.2 (3) | C28—C29—C30—C25 | 2.3 (3) |
C20—C1—C10—C11 | 143.1 (2) | C28—C29—C30—C21 | −178.3 (2) |
S1—C1—C10—C11 | −92.5 (2) | C24—C25—C30—C29 | 175.1 (2) |
C3—C1—C10—C17 | 137.46 (19) | C26—C25—C30—C29 | −4.5 (3) |
C20—C1—C10—C17 | −103.6 (2) | C24—C25—C30—C21 | −4.3 (3) |
S1—C1—C10—C17 | 20.8 (2) | C26—C25—C30—C21 | 176.1 (2) |
N3—C10—C11—C12 | 44.0 (3) | C22—C21—C30—C29 | −176.6 (2) |
C17—C10—C11—C12 | 168.5 (2) | C20—C21—C30—C29 | 5.4 (3) |
C1—C10—C11—C12 | −74.1 (3) | C22—C21—C30—C25 | 2.7 (3) |
N3—C10—C11—C16 | −132.2 (2) | C20—C21—C30—C25 | −175.3 (2) |
C17—C10—C11—C16 | −7.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···N2i | 0.86 | 2.14 | 2.994 (3) | 174 |
Symmetry code: (i) −x, −y+1, −z+1. |