Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805006537/wk6044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805006537/wk6044Isup2.hkl |
CCDC reference: 270563
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C38H42N4O4S | F(000) = 1384 |
Mr = 650.82 | Dx = 1.225 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.641 (2) Å | Cell parameters from 3695 reflections |
b = 14.2886 (18) Å | θ = 2.6–21.2° |
c = 17.112 (2) Å | µ = 0.14 mm−1 |
β = 112.678 (2)° | T = 293 K |
V = 3528.5 (8) Å3 | Block, colorless |
Z = 4 | 0.24 × 0.20 × 0.16 mm |
Bruker SMART1000 CCD area-detector diffractometer | 7258 independent reflections |
Radiation source: fine-focus sealed tube | 3786 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
φ and ω scans | θmax = 26.4°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→13 |
Tmin = 0.831, Tmax = 0.980 | k = −15→17 |
20399 measured reflections | l = −20→21 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.137 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.06P)2] where P = (Fo2 + 2Fc2)/3 |
7258 reflections | (Δ/σ)max = 0.001 |
432 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.22 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 | 0.18276 (4) | 0.09890 (4) | 0.10579 (4) | 0.04380 (18) | |
O1 | 0.29865 (12) | 0.28107 (12) | 0.06513 (12) | 0.0624 (5) | |
O2 | 0.05065 (13) | 0.10526 (12) | −0.07091 (12) | 0.0809 (7) | |
O3 | 0.43902 (12) | 0.07635 (13) | 0.14164 (10) | 0.0625 (5) | |
O4 | 0.26605 (16) | −0.17598 (12) | 0.05474 (12) | 0.0886 (7) | |
N1 | 0.15804 (12) | 0.28328 (11) | 0.07351 (11) | 0.0387 (5) | |
N2 | 0.14677 (12) | 0.19232 (11) | 0.03928 (11) | 0.0401 (5) | |
N3 | 0.28458 (12) | 0.06103 (11) | 0.10537 (11) | 0.0386 (5) | |
N4 | 0.28456 (12) | −0.01929 (12) | 0.05739 (11) | 0.0431 (5) | |
C1 | 0.32239 (18) | 0.44721 (17) | 0.18972 (17) | 0.0636 (8) | |
H1 | 0.3497 | 0.4001 | 0.2289 | 0.076* | |
C2 | 0.3450 (2) | 0.5398 (2) | 0.2120 (2) | 0.0768 (9) | |
H2 | 0.3867 | 0.5549 | 0.2662 | 0.092* | |
C3 | 0.3060 (2) | 0.6091 (2) | 0.1540 (2) | 0.0824 (10) | |
H3 | 0.3207 | 0.6714 | 0.1692 | 0.099* | |
C4 | 0.2460 (2) | 0.58760 (18) | 0.0744 (2) | 0.0796 (9) | |
H4 | 0.2209 | 0.6350 | 0.0349 | 0.096* | |
C5 | 0.2219 (2) | 0.49538 (17) | 0.05198 (17) | 0.0647 (8) | |
H5 | 0.1802 | 0.4811 | −0.0024 | 0.078* | |
C6 | 0.25971 (16) | 0.42423 (15) | 0.11004 (15) | 0.0466 (6) | |
C7 | 0.24138 (17) | 0.32377 (15) | 0.08267 (14) | 0.0432 (6) | |
C8 | 0.09228 (16) | 0.31254 (15) | 0.11553 (15) | 0.0487 (6) | |
C9 | 0.04404 (19) | 0.40447 (16) | 0.07732 (19) | 0.0683 (8) | |
H9A | 0.0887 | 0.4542 | 0.0923 | 0.102* | |
H9B | −0.0029 | 0.4180 | 0.0989 | 0.102* | |
H9C | 0.0160 | 0.3988 | 0.0168 | 0.102* | |
C10 | 0.1456 (2) | 0.3223 (2) | 0.21053 (16) | 0.0743 (9) | |
H10A | 0.1809 | 0.2665 | 0.2322 | 0.111* | |
H10B | 0.1028 | 0.3317 | 0.2377 | 0.111* | |
H10C | 0.1867 | 0.3750 | 0.2217 | 0.111* | |
C11 | 0.01709 (19) | 0.23853 (18) | 0.09930 (19) | 0.0709 (8) | |
H11A | −0.0179 | 0.2330 | 0.0395 | 0.106* | |
H11B | −0.0234 | 0.2565 | 0.1269 | 0.106* | |
H11C | 0.0453 | 0.1794 | 0.1213 | 0.106* | |
C12 | 0.08226 (16) | 0.18109 (16) | −0.04441 (15) | 0.0508 (6) | |
C13 | 0.05762 (18) | 0.26693 (16) | −0.09861 (14) | 0.0483 (6) | |
C14 | 0.1223 (2) | 0.31205 (18) | −0.12003 (16) | 0.0600 (7) | |
H14 | 0.1840 | 0.2934 | −0.0962 | 0.072* | |
C15 | 0.0963 (2) | 0.38597 (19) | −0.17739 (16) | 0.0693 (8) | |
H15 | 0.1403 | 0.4167 | −0.1922 | 0.083* | |
C16 | 0.0047 (3) | 0.4132 (2) | −0.21215 (17) | 0.0750 (9) | |
H16 | −0.0131 | 0.4623 | −0.2508 | 0.090* | |
C17 | −0.0596 (2) | 0.3689 (2) | −0.19025 (19) | 0.0790 (10) | |
H17 | −0.1210 | 0.3887 | −0.2130 | 0.095* | |
C18 | −0.03452 (19) | 0.29474 (18) | −0.13448 (17) | 0.0687 (8) | |
H18 | −0.0791 | 0.2634 | −0.1209 | 0.082* | |
C19 | 0.37300 (17) | 0.09525 (15) | 0.15817 (14) | 0.0422 (6) | |
C20 | 0.38369 (16) | 0.14825 (15) | 0.23660 (14) | 0.0427 (6) | |
C21 | 0.45140 (18) | 0.21683 (17) | 0.26232 (16) | 0.0617 (7) | |
H21 | 0.4810 | 0.2346 | 0.2268 | 0.074* | |
C22 | 0.4751 (2) | 0.2588 (2) | 0.34026 (19) | 0.0781 (9) | |
H22 | 0.5200 | 0.3054 | 0.3568 | 0.094* | |
C23 | 0.4336 (2) | 0.2327 (2) | 0.39305 (18) | 0.0761 (9) | |
H23 | 0.4501 | 0.2615 | 0.4456 | 0.091* | |
C24 | 0.3668 (2) | 0.1637 (2) | 0.36929 (16) | 0.0665 (8) | |
H24 | 0.3389 | 0.1454 | 0.4060 | 0.080* | |
C25 | 0.34160 (17) | 0.12190 (17) | 0.29072 (15) | 0.0526 (6) | |
H25 | 0.2961 | 0.0758 | 0.2743 | 0.063* | |
C26 | 0.28963 (18) | −0.01368 (17) | −0.02868 (14) | 0.0546 (7) | |
C27 | 0.3011 (2) | 0.08817 (18) | −0.04878 (16) | 0.0700 (8) | |
H27A | 0.2485 | 0.1236 | −0.0497 | 0.105* | |
H27B | 0.3055 | 0.0921 | −0.1031 | 0.105* | |
H27C | 0.3565 | 0.1131 | −0.0062 | 0.105* | |
C28 | 0.2007 (2) | −0.0523 (2) | −0.09553 (17) | 0.0840 (10) | |
H28A | 0.1968 | −0.1182 | −0.0868 | 0.126* | |
H28B | 0.2010 | −0.0416 | −0.1508 | 0.126* | |
H28C | 0.1483 | −0.0213 | −0.0911 | 0.126* | |
C29 | 0.3740 (2) | −0.0698 (2) | −0.02618 (18) | 0.0808 (9) | |
H29A | 0.4284 | −0.0473 | 0.0191 | 0.121* | |
H29B | 0.3814 | −0.0627 | −0.0790 | 0.121* | |
H29C | 0.3650 | −0.1348 | −0.0171 | 0.121* | |
C30 | 0.27883 (18) | −0.10227 (17) | 0.09388 (16) | 0.0537 (7) | |
C31 | 0.29158 (19) | −0.10267 (15) | 0.18538 (16) | 0.0512 (6) | |
C32 | 0.2164 (2) | −0.11522 (16) | 0.20802 (19) | 0.0646 (8) | |
H32 | 0.1568 | −0.1166 | 0.1664 | 0.078* | |
C33 | 0.2297 (3) | −0.12578 (19) | 0.2927 (2) | 0.0755 (9) | |
C34 | 0.3190 (3) | −0.1218 (2) | 0.3531 (2) | 0.0824 (10) | |
H34 | 0.3282 | −0.1297 | 0.4097 | 0.099* | |
C35 | 0.3951 (2) | −0.1067 (2) | 0.33262 (18) | 0.0762 (9) | |
C36 | 0.3799 (2) | −0.09913 (17) | 0.24762 (17) | 0.0617 (7) | |
H36 | 0.4303 | −0.0915 | 0.2321 | 0.074* | |
C37 | 0.1478 (3) | −0.1428 (2) | 0.3175 (2) | 0.1122 (13) | |
H37A | 0.0919 | −0.1228 | 0.2724 | 0.168* | |
H37B | 0.1560 | −0.1081 | 0.3679 | 0.168* | |
H37C | 0.1437 | −0.2084 | 0.3278 | 0.168* | |
C38 | 0.4921 (3) | −0.0956 (3) | 0.4003 (2) | 0.1285 (16) | |
H38A | 0.5273 | −0.1514 | 0.4025 | 0.193* | |
H38B | 0.4883 | −0.0856 | 0.4543 | 0.193* | |
H38C | 0.5221 | −0.0431 | 0.3867 | 0.193* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0417 (4) | 0.0363 (3) | 0.0508 (4) | 0.0017 (3) | 0.0150 (3) | 0.0065 (3) |
O1 | 0.0471 (11) | 0.0507 (10) | 0.0920 (14) | −0.0024 (9) | 0.0295 (10) | −0.0076 (9) |
O2 | 0.0805 (14) | 0.0429 (10) | 0.0781 (14) | −0.0077 (10) | −0.0150 (11) | −0.0087 (9) |
O3 | 0.0428 (11) | 0.0921 (14) | 0.0526 (11) | 0.0001 (9) | 0.0184 (9) | −0.0125 (9) |
O4 | 0.154 (2) | 0.0363 (10) | 0.0727 (13) | −0.0017 (11) | 0.0410 (13) | −0.0064 (9) |
N1 | 0.0401 (11) | 0.0305 (10) | 0.0429 (11) | 0.0007 (8) | 0.0133 (9) | −0.0008 (8) |
N2 | 0.0390 (11) | 0.0296 (10) | 0.0447 (11) | 0.0010 (8) | 0.0081 (9) | 0.0005 (8) |
N3 | 0.0410 (11) | 0.0311 (10) | 0.0378 (10) | 0.0012 (8) | 0.0087 (9) | −0.0016 (8) |
N4 | 0.0544 (12) | 0.0324 (10) | 0.0379 (11) | 0.0026 (9) | 0.0127 (9) | −0.0018 (8) |
C1 | 0.0605 (18) | 0.0490 (16) | 0.0642 (18) | −0.0031 (13) | 0.0053 (15) | −0.0035 (13) |
C2 | 0.069 (2) | 0.065 (2) | 0.080 (2) | −0.0141 (16) | 0.0098 (16) | −0.0226 (17) |
C3 | 0.089 (2) | 0.0434 (17) | 0.113 (3) | −0.0164 (16) | 0.036 (2) | −0.0104 (18) |
C4 | 0.100 (2) | 0.0422 (16) | 0.093 (3) | −0.0055 (16) | 0.033 (2) | 0.0134 (15) |
C5 | 0.081 (2) | 0.0418 (15) | 0.0621 (17) | −0.0041 (14) | 0.0172 (15) | 0.0061 (13) |
C6 | 0.0464 (15) | 0.0365 (13) | 0.0515 (15) | −0.0043 (11) | 0.0131 (12) | 0.0016 (11) |
C7 | 0.0426 (15) | 0.0405 (13) | 0.0400 (14) | 0.0011 (12) | 0.0088 (12) | 0.0062 (10) |
C8 | 0.0533 (16) | 0.0421 (14) | 0.0569 (16) | 0.0025 (12) | 0.0281 (13) | −0.0004 (12) |
C9 | 0.075 (2) | 0.0455 (15) | 0.093 (2) | 0.0170 (14) | 0.0420 (17) | 0.0058 (14) |
C10 | 0.091 (2) | 0.087 (2) | 0.0566 (19) | −0.0044 (17) | 0.0413 (17) | −0.0038 (15) |
C11 | 0.0633 (19) | 0.0585 (17) | 0.104 (2) | 0.0014 (14) | 0.0467 (17) | 0.0014 (16) |
C12 | 0.0423 (15) | 0.0430 (15) | 0.0517 (16) | 0.0030 (12) | 0.0013 (12) | −0.0034 (12) |
C13 | 0.0506 (16) | 0.0428 (14) | 0.0382 (14) | 0.0062 (12) | 0.0025 (12) | −0.0044 (11) |
C14 | 0.0654 (19) | 0.0610 (17) | 0.0486 (16) | 0.0153 (15) | 0.0165 (14) | 0.0028 (13) |
C15 | 0.091 (2) | 0.0652 (18) | 0.0526 (17) | 0.0093 (17) | 0.0284 (17) | 0.0070 (14) |
C16 | 0.102 (3) | 0.0606 (19) | 0.0427 (17) | 0.0243 (19) | 0.0058 (17) | 0.0103 (13) |
C17 | 0.072 (2) | 0.070 (2) | 0.064 (2) | 0.0176 (17) | −0.0097 (17) | 0.0042 (16) |
C18 | 0.0574 (19) | 0.0566 (17) | 0.0663 (19) | 0.0020 (14) | −0.0047 (15) | 0.0008 (14) |
C19 | 0.0431 (15) | 0.0435 (13) | 0.0360 (13) | 0.0003 (12) | 0.0107 (12) | 0.0034 (10) |
C20 | 0.0415 (14) | 0.0433 (13) | 0.0354 (13) | 0.0027 (11) | 0.0062 (11) | 0.0000 (11) |
C21 | 0.0675 (19) | 0.0592 (16) | 0.0488 (16) | −0.0124 (14) | 0.0118 (14) | −0.0036 (13) |
C22 | 0.097 (3) | 0.0646 (19) | 0.0560 (19) | −0.0199 (17) | 0.0114 (18) | −0.0131 (16) |
C23 | 0.095 (2) | 0.070 (2) | 0.0450 (17) | 0.0099 (18) | 0.0069 (17) | −0.0172 (15) |
C24 | 0.076 (2) | 0.079 (2) | 0.0428 (16) | 0.0200 (17) | 0.0207 (15) | 0.0003 (14) |
C25 | 0.0519 (16) | 0.0592 (16) | 0.0436 (15) | 0.0054 (12) | 0.0152 (13) | 0.0014 (12) |
C26 | 0.0688 (18) | 0.0540 (15) | 0.0336 (14) | 0.0077 (13) | 0.0117 (13) | 0.0002 (11) |
C27 | 0.099 (2) | 0.0662 (18) | 0.0443 (15) | 0.0010 (16) | 0.0274 (15) | 0.0084 (13) |
C28 | 0.102 (3) | 0.076 (2) | 0.0479 (17) | −0.0014 (18) | −0.0009 (16) | −0.0101 (15) |
C29 | 0.098 (2) | 0.093 (2) | 0.0582 (19) | 0.0297 (19) | 0.0376 (17) | 0.0030 (16) |
C30 | 0.0665 (17) | 0.0364 (14) | 0.0534 (16) | 0.0060 (13) | 0.0179 (13) | 0.0002 (13) |
C31 | 0.0682 (19) | 0.0308 (13) | 0.0569 (17) | 0.0073 (12) | 0.0265 (15) | 0.0089 (11) |
C32 | 0.076 (2) | 0.0390 (15) | 0.085 (2) | −0.0064 (13) | 0.0377 (17) | −0.0059 (14) |
C33 | 0.105 (3) | 0.0533 (18) | 0.094 (3) | −0.0043 (17) | 0.067 (2) | −0.0006 (16) |
C34 | 0.119 (3) | 0.079 (2) | 0.066 (2) | 0.020 (2) | 0.054 (2) | 0.0242 (17) |
C35 | 0.085 (2) | 0.092 (2) | 0.0569 (19) | 0.0354 (18) | 0.0341 (18) | 0.0262 (16) |
C36 | 0.0707 (19) | 0.0652 (17) | 0.0571 (18) | 0.0253 (15) | 0.0333 (15) | 0.0203 (14) |
C37 | 0.144 (3) | 0.093 (2) | 0.147 (3) | −0.038 (2) | 0.109 (3) | −0.029 (2) |
C38 | 0.097 (3) | 0.216 (5) | 0.062 (2) | 0.060 (3) | 0.019 (2) | 0.033 (3) |
S1—N3 | 1.6846 (19) | C16—H16 | 0.9300 |
S1—N2 | 1.7029 (17) | C17—C18 | 1.378 (4) |
O1—C7 | 1.213 (3) | C17—H17 | 0.9300 |
O2—C12 | 1.205 (3) | C18—H18 | 0.9300 |
O3—C19 | 1.202 (3) | C19—C20 | 1.493 (3) |
O4—C30 | 1.223 (3) | C20—C25 | 1.379 (3) |
N1—C7 | 1.379 (3) | C20—C21 | 1.384 (3) |
N1—N2 | 1.408 (2) | C21—C22 | 1.376 (4) |
N1—C8 | 1.523 (3) | C21—H21 | 0.9300 |
N2—C12 | 1.407 (3) | C22—C23 | 1.352 (4) |
N3—N4 | 1.411 (2) | C22—H22 | 0.9300 |
N3—C19 | 1.416 (3) | C23—C24 | 1.379 (4) |
N4—C30 | 1.359 (3) | C23—H23 | 0.9300 |
N4—C26 | 1.507 (3) | C24—C25 | 1.383 (3) |
C1—C6 | 1.377 (3) | C24—H24 | 0.9300 |
C1—C2 | 1.385 (3) | C25—H25 | 0.9300 |
C1—H1 | 0.9300 | C26—C27 | 1.522 (3) |
C2—C3 | 1.367 (4) | C26—C28 | 1.523 (3) |
C2—H2 | 0.9300 | C26—C29 | 1.531 (4) |
C3—C4 | 1.359 (4) | C27—H27A | 0.9600 |
C3—H3 | 0.9300 | C27—H27B | 0.9600 |
C4—C5 | 1.383 (4) | C27—H27C | 0.9600 |
C4—H4 | 0.9300 | C28—H28A | 0.9600 |
C5—C6 | 1.385 (3) | C28—H28B | 0.9600 |
C5—H5 | 0.9300 | C28—H28C | 0.9600 |
C6—C7 | 1.503 (3) | C29—H29A | 0.9600 |
C8—C10 | 1.521 (3) | C29—H29B | 0.9600 |
C8—C11 | 1.525 (3) | C29—H29C | 0.9600 |
C8—C9 | 1.530 (3) | C30—C31 | 1.500 (3) |
C9—H9A | 0.9600 | C31—C36 | 1.382 (3) |
C9—H9B | 0.9600 | C31—C32 | 1.384 (4) |
C9—H9C | 0.9600 | C32—C33 | 1.391 (4) |
C10—H10A | 0.9600 | C32—H32 | 0.9300 |
C10—H10B | 0.9600 | C33—C34 | 1.380 (4) |
C10—H10C | 0.9600 | C33—C37 | 1.515 (4) |
C11—H11A | 0.9600 | C34—C35 | 1.381 (4) |
C11—H11B | 0.9600 | C34—H34 | 0.9300 |
C11—H11C | 0.9600 | C35—C36 | 1.385 (4) |
C12—C13 | 1.496 (3) | C35—C38 | 1.521 (4) |
C13—C14 | 1.364 (3) | C36—H36 | 0.9300 |
C13—C18 | 1.389 (3) | C37—H37A | 0.9600 |
C14—C15 | 1.392 (3) | C37—H37B | 0.9600 |
C14—H14 | 0.9300 | C37—H37C | 0.9600 |
C15—C16 | 1.379 (4) | C38—H38A | 0.9600 |
C15—H15 | 0.9300 | C38—H38B | 0.9600 |
C16—C17 | 1.358 (4) | C38—H38C | 0.9600 |
N3—S1—N2 | 108.57 (9) | O3—C19—N3 | 119.2 (2) |
C7—N1—N2 | 113.31 (17) | O3—C19—C20 | 121.1 (2) |
C7—N1—C8 | 127.74 (18) | N3—C19—C20 | 119.5 (2) |
N2—N1—C8 | 116.78 (16) | C25—C20—C21 | 119.0 (2) |
C12—N2—N1 | 117.01 (16) | C25—C20—C19 | 123.2 (2) |
C12—N2—S1 | 120.88 (14) | C21—C20—C19 | 116.9 (2) |
N1—N2—S1 | 119.30 (13) | C22—C21—C20 | 120.2 (3) |
N4—N3—C19 | 115.68 (17) | C22—C21—H21 | 119.9 |
N4—N3—S1 | 118.39 (13) | C20—C21—H21 | 119.9 |
C19—N3—S1 | 125.36 (15) | C23—C22—C21 | 120.5 (3) |
C30—N4—N3 | 115.31 (18) | C23—C22—H22 | 119.7 |
C30—N4—C26 | 122.21 (19) | C21—C22—H22 | 119.7 |
N3—N4—C26 | 122.48 (17) | C22—C23—C24 | 120.3 (3) |
C6—C1—C2 | 120.6 (2) | C22—C23—H23 | 119.9 |
C6—C1—H1 | 119.7 | C24—C23—H23 | 119.9 |
C2—C1—H1 | 119.7 | C23—C24—C25 | 119.7 (3) |
C3—C2—C1 | 119.8 (3) | C23—C24—H24 | 120.1 |
C3—C2—H2 | 120.1 | C25—C24—H24 | 120.1 |
C1—C2—H2 | 120.1 | C20—C25—C24 | 120.2 (3) |
C4—C3—C2 | 120.4 (3) | C20—C25—H25 | 119.9 |
C4—C3—H3 | 119.8 | C24—C25—H25 | 119.9 |
C2—C3—H3 | 119.8 | N4—C26—C27 | 109.08 (19) |
C3—C4—C5 | 120.2 (3) | N4—C26—C28 | 109.7 (2) |
C3—C4—H4 | 119.9 | C27—C26—C28 | 109.2 (2) |
C5—C4—H4 | 119.9 | N4—C26—C29 | 108.32 (18) |
C4—C5—C6 | 120.4 (3) | C27—C26—C29 | 109.4 (2) |
C4—C5—H5 | 119.8 | C28—C26—C29 | 111.0 (2) |
C6—C5—H5 | 119.8 | C26—C27—H27A | 109.5 |
C1—C6—C5 | 118.6 (2) | C26—C27—H27B | 109.5 |
C1—C6—C7 | 120.9 (2) | H27A—C27—H27B | 109.5 |
C5—C6—C7 | 120.0 (2) | C26—C27—H27C | 109.5 |
O1—C7—N1 | 121.1 (2) | H27A—C27—H27C | 109.5 |
O1—C7—C6 | 119.1 (2) | H27B—C27—H27C | 109.5 |
N1—C7—C6 | 119.6 (2) | C26—C28—H28A | 109.5 |
C10—C8—N1 | 109.78 (19) | C26—C28—H28B | 109.5 |
C10—C8—C11 | 109.0 (2) | H28A—C28—H28B | 109.5 |
N1—C8—C11 | 109.71 (19) | C26—C28—H28C | 109.5 |
C10—C8—C9 | 110.8 (2) | H28A—C28—H28C | 109.5 |
N1—C8—C9 | 110.20 (19) | H28B—C28—H28C | 109.5 |
C11—C8—C9 | 107.4 (2) | C26—C29—H29A | 109.5 |
C8—C9—H9A | 109.5 | C26—C29—H29B | 109.5 |
C8—C9—H9B | 109.5 | H29A—C29—H29B | 109.5 |
H9A—C9—H9B | 109.5 | C26—C29—H29C | 109.5 |
C8—C9—H9C | 109.5 | H29A—C29—H29C | 109.5 |
H9A—C9—H9C | 109.5 | H29B—C29—H29C | 109.5 |
H9B—C9—H9C | 109.5 | O4—C30—N4 | 121.7 (2) |
C8—C10—H10A | 109.5 | O4—C30—C31 | 119.8 (2) |
C8—C10—H10B | 109.5 | N4—C30—C31 | 118.5 (2) |
H10A—C10—H10B | 109.5 | C36—C31—C32 | 119.6 (3) |
C8—C10—H10C | 109.5 | C36—C31—C30 | 119.7 (2) |
H10A—C10—H10C | 109.5 | C32—C31—C30 | 120.5 (3) |
H10B—C10—H10C | 109.5 | C31—C32—C33 | 120.3 (3) |
C8—C11—H11A | 109.5 | C31—C32—H32 | 119.9 |
C8—C11—H11B | 109.5 | C33—C32—H32 | 119.9 |
H11A—C11—H11B | 109.5 | C34—C33—C32 | 118.4 (3) |
C8—C11—H11C | 109.5 | C34—C33—C37 | 121.2 (3) |
H11A—C11—H11C | 109.5 | C32—C33—C37 | 120.4 (4) |
H11B—C11—H11C | 109.5 | C33—C34—C35 | 122.6 (3) |
O2—C12—N2 | 121.0 (2) | C33—C34—H34 | 118.7 |
O2—C12—C13 | 122.3 (2) | C35—C34—H34 | 118.7 |
N2—C12—C13 | 116.73 (19) | C34—C35—C36 | 117.6 (3) |
C14—C13—C18 | 119.8 (2) | C34—C35—C38 | 121.9 (3) |
C14—C13—C12 | 120.9 (2) | C36—C35—C38 | 120.5 (3) |
C18—C13—C12 | 118.9 (2) | C31—C36—C35 | 121.5 (3) |
C13—C14—C15 | 120.2 (3) | C31—C36—H36 | 119.3 |
C13—C14—H14 | 119.9 | C35—C36—H36 | 119.3 |
C15—C14—H14 | 119.9 | C33—C37—H37A | 109.5 |
C16—C15—C14 | 119.4 (3) | C33—C37—H37B | 109.5 |
C16—C15—H15 | 120.3 | H37A—C37—H37B | 109.5 |
C14—C15—H15 | 120.3 | C33—C37—H37C | 109.5 |
C17—C16—C15 | 120.4 (3) | H37A—C37—H37C | 109.5 |
C17—C16—H16 | 119.8 | H37B—C37—H37C | 109.5 |
C15—C16—H16 | 119.8 | C35—C38—H38A | 109.5 |
C16—C17—C18 | 120.4 (3) | C35—C38—H38B | 109.5 |
C16—C17—H17 | 119.8 | H38A—C38—H38B | 109.5 |
C18—C17—H17 | 119.8 | C35—C38—H38C | 109.5 |
C17—C18—C13 | 119.7 (3) | H38A—C38—H38C | 109.5 |
C17—C18—H18 | 120.1 | H38B—C38—H38C | 109.5 |
C13—C18—H18 | 120.1 | ||
C7—N1—N2—C12 | −108.5 (2) | C15—C16—C17—C18 | −1.5 (5) |
C8—N1—N2—C12 | 86.9 (2) | C16—C17—C18—C13 | 1.8 (4) |
C7—N1—N2—S1 | 90.35 (19) | C14—C13—C18—C17 | −1.2 (4) |
C8—N1—N2—S1 | −74.2 (2) | C12—C13—C18—C17 | −174.5 (2) |
N3—S1—N2—C12 | 97.32 (19) | N4—N3—C19—O3 | 23.0 (3) |
N3—S1—N2—N1 | −102.25 (16) | S1—N3—C19—O3 | −165.82 (17) |
N2—S1—N3—N4 | −101.87 (15) | N4—N3—C19—C20 | −152.68 (18) |
N2—S1—N3—C19 | 87.14 (18) | S1—N3—C19—C20 | 18.5 (3) |
C19—N3—N4—C30 | 93.1 (2) | O3—C19—C20—C25 | −133.1 (3) |
S1—N3—N4—C30 | −78.8 (2) | N3—C19—C20—C25 | 42.5 (3) |
C19—N3—N4—C26 | −87.4 (2) | O3—C19—C20—C21 | 35.6 (3) |
S1—N3—N4—C26 | 100.7 (2) | N3—C19—C20—C21 | −148.8 (2) |
C6—C1—C2—C3 | −1.0 (5) | C25—C20—C21—C22 | −1.0 (4) |
C1—C2—C3—C4 | −0.8 (5) | C19—C20—C21—C22 | −170.1 (2) |
C2—C3—C4—C5 | 1.7 (5) | C20—C21—C22—C23 | 0.9 (4) |
C3—C4—C5—C6 | −0.8 (5) | C21—C22—C23—C24 | 0.0 (5) |
C2—C1—C6—C5 | 1.8 (4) | C22—C23—C24—C25 | −0.8 (4) |
C2—C1—C6—C7 | 174.3 (3) | C21—C20—C25—C24 | 0.1 (4) |
C4—C5—C6—C1 | −0.9 (4) | C19—C20—C25—C24 | 168.6 (2) |
C4—C5—C6—C7 | −173.4 (3) | C23—C24—C25—C20 | 0.7 (4) |
N2—N1—C7—O1 | −2.6 (3) | C30—N4—C26—C27 | −176.7 (2) |
C8—N1—C7—O1 | 159.9 (2) | N3—N4—C26—C27 | 3.8 (3) |
N2—N1—C7—C6 | 173.82 (18) | C30—N4—C26—C28 | 63.6 (3) |
C8—N1—C7—C6 | −23.6 (3) | N3—N4—C26—C28 | −115.8 (2) |
C1—C6—C7—O1 | −74.8 (3) | C30—N4—C26—C29 | −57.7 (3) |
C5—C6—C7—O1 | 97.6 (3) | N3—N4—C26—C29 | 122.9 (2) |
C1—C6—C7—N1 | 108.7 (3) | N3—N4—C30—O4 | 170.3 (2) |
C5—C6—C7—N1 | −79.0 (3) | C26—N4—C30—O4 | −9.1 (4) |
C7—N1—C8—C10 | −50.7 (3) | N3—N4—C30—C31 | −11.6 (3) |
N2—N1—C8—C10 | 111.4 (2) | C26—N4—C30—C31 | 168.9 (2) |
C7—N1—C8—C11 | −170.4 (2) | O4—C30—C31—C36 | 98.5 (3) |
N2—N1—C8—C11 | −8.3 (3) | N4—C30—C31—C36 | −79.6 (3) |
C7—N1—C8—C9 | 71.6 (3) | O4—C30—C31—C32 | −75.5 (3) |
N2—N1—C8—C9 | −126.4 (2) | N4—C30—C31—C32 | 106.4 (3) |
N1—N2—C12—O2 | −160.5 (2) | C36—C31—C32—C33 | −1.1 (4) |
S1—N2—C12—O2 | 0.3 (3) | C30—C31—C32—C33 | 173.0 (2) |
N1—N2—C12—C13 | 21.2 (3) | C31—C32—C33—C34 | 1.1 (4) |
S1—N2—C12—C13 | −177.95 (17) | C31—C32—C33—C37 | −177.9 (2) |
O2—C12—C13—C14 | −113.5 (3) | C32—C33—C34—C35 | 0.9 (5) |
N2—C12—C13—C14 | 64.8 (3) | C37—C33—C34—C35 | 179.8 (3) |
O2—C12—C13—C18 | 59.8 (4) | C33—C34—C35—C36 | −2.7 (5) |
N2—C12—C13—C18 | −122.0 (2) | C33—C34—C35—C38 | 175.6 (3) |
C18—C13—C14—C15 | 0.2 (4) | C32—C31—C36—C35 | −0.9 (4) |
C12—C13—C14—C15 | 173.4 (2) | C30—C31—C36—C35 | −174.9 (2) |
C13—C14—C15—C16 | 0.1 (4) | C34—C35—C36—C31 | 2.7 (4) |
C14—C15—C16—C17 | 0.5 (4) | C38—C35—C36—C31 | −175.6 (3) |