Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806009834/ww2011sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806009834/ww2011Isup2.hkl |
CCDC reference: 605255
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.
C19H15NO2S | Z = 4 |
Mr = 321.38 | F(000) = 672 |
Triclinic, P1 | Dx = 1.323 Mg m−3 |
Hall symbol: -P 1 | Melting point = 393–394 K |
a = 10.0889 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.8104 (19) Å | Cell parameters from 2826 reflections |
c = 15.884 (3) Å | θ = 2.6–26.3° |
α = 77.896 (3)° | µ = 0.21 mm−1 |
β = 72.353 (3)° | T = 294 K |
γ = 84.459 (3)° | Rod, colourless |
V = 1613.1 (5) Å3 | 0.30 × 0.26 × 0.14 mm |
Bruker SMART CCD area-detector diffractometer | 5640 independent reflections |
Radiation source: fine-focus sealed tube | 3776 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.023 |
φ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −11→9 |
Tmin = 0.940, Tmax = 0.971 | k = −10→12 |
8234 measured reflections | l = −18→18 |
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)] = 0.043 | H-atom parameters constrained |
wR(F2) = 0.125 | w = 1/[σ2(Fo2) + (0.06P)2 + 0.1686P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
5640 reflections | Δρmax = 0.21 e Å−3 |
418 parameters | Δρmin = −0.29 e Å−3 |
6 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0131 (14) |
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 | 0.40767 (6) | 0.20500 (6) | 0.10161 (4) | 0.0511 (2) | |
S2 | 0.77776 (8) | 0.42973 (7) | 0.41574 (4) | 0.0661 (2) | |
O1 | 0.41336 (19) | 0.33737 (15) | 0.09462 (11) | 0.0636 (5) | |
O2 | 0.50129 (17) | 0.14237 (17) | 0.03524 (10) | 0.0653 (5) | |
O3 | 0.6312 (2) | 0.4362 (2) | 0.43287 (12) | 0.0876 (6) | |
O4 | 0.8396 (2) | 0.4692 (2) | 0.47468 (12) | 0.0919 (7) | |
N1 | 0.43643 (19) | 0.13765 (18) | 0.19921 (12) | 0.0475 (5) | |
N2 | 0.8424 (2) | 0.52053 (18) | 0.31513 (13) | 0.0559 (5) | |
C1 | 0.3944 (2) | 0.1911 (2) | 0.27900 (15) | 0.0469 (6) | |
C2 | 0.3499 (3) | 0.3133 (2) | 0.29099 (16) | 0.0570 (6) | |
H2 | 0.3391 | 0.3759 | 0.2433 | 0.068* | |
C3 | 0.3220 (3) | 0.3386 (3) | 0.37665 (18) | 0.0635 (7) | |
H3 | 0.2921 | 0.4199 | 0.3865 | 0.076* | |
C4 | 0.3375 (3) | 0.2459 (3) | 0.44817 (17) | 0.0686 (8) | |
H4 | 0.3189 | 0.2659 | 0.5049 | 0.082* | |
C5 | 0.3801 (3) | 0.1249 (3) | 0.43603 (16) | 0.0630 (7) | |
H5 | 0.3899 | 0.0628 | 0.4843 | 0.076* | |
C6 | 0.4087 (2) | 0.0958 (2) | 0.35075 (15) | 0.0496 (6) | |
C7 | 0.4539 (2) | −0.0198 (2) | 0.31677 (16) | 0.0504 (6) | |
C8 | 0.4833 (3) | −0.1420 (3) | 0.35884 (19) | 0.0693 (8) | |
H8 | 0.4718 | −0.1608 | 0.4205 | 0.083* | |
C9 | 0.5293 (3) | −0.2333 (3) | 0.3075 (2) | 0.0798 (9) | |
H9 | 0.5501 | −0.3148 | 0.3344 | 0.096* | |
C10 | 0.5451 (3) | −0.2057 (3) | 0.2161 (2) | 0.0741 (8) | |
H10 | 0.5768 | −0.2693 | 0.1827 | 0.089* | |
C11 | 0.5151 (3) | −0.0865 (3) | 0.17298 (18) | 0.0600 (7) | |
H11 | 0.5249 | −0.0691 | 0.1116 | 0.072* | |
C12 | 0.4699 (2) | 0.0065 (2) | 0.22460 (16) | 0.0475 (6) | |
C13 | 0.2366 (2) | 0.1695 (2) | 0.11264 (14) | 0.0458 (6) | |
C14 | 0.1276 (3) | 0.2516 (2) | 0.14427 (15) | 0.0543 (6) | |
H14 | 0.1445 | 0.3246 | 0.1610 | 0.065* | |
C15 | −0.0057 (3) | 0.2248 (3) | 0.15078 (17) | 0.0641 (7) | |
H15 | −0.0784 | 0.2808 | 0.1715 | 0.077* | |
C16 | −0.0342 (3) | 0.1164 (3) | 0.12732 (18) | 0.0677 (8) | |
C17 | 0.0764 (3) | 0.0346 (3) | 0.0973 (2) | 0.0736 (8) | |
H17 | 0.0588 | −0.0393 | 0.0820 | 0.088* | |
C18 | 0.2113 (3) | 0.0591 (2) | 0.08933 (17) | 0.0632 (7) | |
H18 | 0.2840 | 0.0029 | 0.0688 | 0.076* | |
C19 | −0.1824 (3) | 0.0881 (4) | 0.1346 (2) | 0.1081 (12) | |
H19A | −0.2465 | 0.1300 | 0.1790 | 0.162* | |
H19B | −0.1946 | −0.0016 | 0.1519 | 0.162* | |
H19C | −0.1996 | 0.1181 | 0.0774 | 0.162* | |
C20 | 0.9792 (3) | 0.5706 (2) | 0.28108 (19) | 0.0576 (7) | |
C21 | 1.0700 (3) | 0.5920 (3) | 0.3272 (2) | 0.0756 (8) | |
H21 | 1.0473 | 0.5717 | 0.3896 | 0.091* | |
C22 | 1.1959 (4) | 0.6451 (3) | 0.2753 (3) | 0.0927 (11) | |
H22 | 1.2588 | 0.6604 | 0.3040 | 0.111* | |
C23 | 1.2308 (4) | 0.6757 (3) | 0.1828 (3) | 0.0994 (11) | |
H23 | 1.3163 | 0.7109 | 0.1504 | 0.119* | |
C24 | 1.1406 (3) | 0.6547 (3) | 0.1381 (2) | 0.0842 (9) | |
H24 | 1.1642 | 0.6756 | 0.0757 | 0.101* | |
C25 | 1.0133 (3) | 0.6018 (2) | 0.18769 (19) | 0.0614 (7) | |
C26 | 0.8986 (3) | 0.5678 (2) | 0.16100 (17) | 0.0580 (7) | |
C27 | 0.8766 (3) | 0.5775 (3) | 0.07791 (19) | 0.0756 (8) | |
H27 | 0.9420 | 0.6147 | 0.0257 | 0.091* | |
C28 | 0.7573 (4) | 0.5316 (3) | 0.0735 (2) | 0.0781 (9) | |
H28 | 0.7424 | 0.5369 | 0.0179 | 0.094* | |
C29 | 0.6590 (3) | 0.4776 (3) | 0.1511 (2) | 0.0708 (8) | |
H29 | 0.5795 | 0.4459 | 0.1465 | 0.085* | |
C30 | 0.6759 (3) | 0.4695 (2) | 0.23570 (18) | 0.0622 (7) | |
H30 | 0.6085 | 0.4349 | 0.2878 | 0.075* | |
C31 | 0.7969 (3) | 0.5152 (2) | 0.23915 (16) | 0.0533 (6) | |
C32 | 0.8388 (3) | 0.2767 (2) | 0.40154 (15) | 0.0566 (6) | |
C33 | 0.7581 (3) | 0.1967 (3) | 0.38127 (17) | 0.0701 (8) | |
H33 | 0.6691 | 0.2226 | 0.3776 | 0.084* | |
C34 | 0.8115 (4) | 0.0786 (3) | 0.36672 (19) | 0.0852 (10) | |
H34 | 0.7575 | 0.0253 | 0.3528 | 0.102* | |
C35 | 0.9419 (5) | 0.0369 (3) | 0.3721 (2) | 0.0932 (11) | |
C36 | 1.0200 (4) | 0.1172 (4) | 0.3933 (2) | 0.0969 (11) | |
H36 | 1.1083 | 0.0900 | 0.3980 | 0.116* | |
C37 | 0.9706 (3) | 0.2369 (3) | 0.4077 (2) | 0.0776 (8) | |
H37 | 1.0251 | 0.2899 | 0.4214 | 0.093* | |
C38 | 1.0001 (5) | −0.0921 (3) | 0.3547 (3) | 0.1418 (17) | |
H38A | 1.0982 | −0.0972 | 0.3482 | 0.213* | |
H38B | 0.9850 | −0.1055 | 0.3005 | 0.213* | |
H38C | 0.9544 | −0.1558 | 0.4044 | 0.213* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0519 (4) | 0.0642 (4) | 0.0385 (3) | −0.0093 (3) | −0.0132 (3) | −0.0096 (3) |
S2 | 0.0697 (5) | 0.0854 (5) | 0.0454 (4) | 0.0137 (4) | −0.0167 (3) | −0.0249 (4) |
O1 | 0.0828 (13) | 0.0586 (11) | 0.0536 (10) | −0.0194 (9) | −0.0282 (9) | 0.0000 (8) |
O2 | 0.0553 (11) | 0.0967 (14) | 0.0427 (10) | −0.0048 (9) | −0.0054 (8) | −0.0225 (9) |
O3 | 0.0639 (13) | 0.1239 (18) | 0.0659 (13) | 0.0221 (12) | −0.0036 (10) | −0.0321 (12) |
O4 | 0.1201 (18) | 0.1134 (17) | 0.0576 (12) | 0.0096 (13) | −0.0374 (12) | −0.0393 (12) |
N1 | 0.0522 (12) | 0.0552 (12) | 0.0378 (11) | 0.0011 (9) | −0.0151 (9) | −0.0128 (9) |
N2 | 0.0666 (14) | 0.0574 (13) | 0.0513 (12) | 0.0071 (10) | −0.0266 (10) | −0.0172 (10) |
C1 | 0.0429 (13) | 0.0596 (16) | 0.0404 (13) | −0.0024 (11) | −0.0125 (10) | −0.0138 (11) |
C2 | 0.0616 (17) | 0.0609 (17) | 0.0512 (15) | 0.0025 (13) | −0.0193 (12) | −0.0142 (12) |
C3 | 0.0656 (18) | 0.0678 (18) | 0.0627 (17) | 0.0081 (13) | −0.0197 (14) | −0.0278 (15) |
C4 | 0.0727 (19) | 0.092 (2) | 0.0459 (16) | 0.0102 (16) | −0.0191 (13) | −0.0270 (15) |
C5 | 0.0702 (18) | 0.0773 (19) | 0.0425 (15) | 0.0070 (14) | −0.0213 (13) | −0.0105 (13) |
C6 | 0.0448 (14) | 0.0606 (15) | 0.0447 (14) | 0.0022 (11) | −0.0153 (11) | −0.0111 (12) |
C7 | 0.0453 (14) | 0.0577 (16) | 0.0523 (15) | −0.0001 (11) | −0.0206 (11) | −0.0108 (12) |
C8 | 0.081 (2) | 0.0649 (19) | 0.0674 (18) | 0.0068 (15) | −0.0347 (15) | −0.0091 (15) |
C9 | 0.088 (2) | 0.0608 (19) | 0.100 (3) | 0.0113 (16) | −0.0464 (19) | −0.0154 (18) |
C10 | 0.074 (2) | 0.067 (2) | 0.094 (2) | 0.0130 (15) | −0.0347 (17) | −0.0336 (17) |
C11 | 0.0570 (16) | 0.0682 (18) | 0.0644 (17) | 0.0037 (13) | −0.0240 (13) | −0.0272 (14) |
C12 | 0.0383 (13) | 0.0554 (15) | 0.0532 (15) | −0.0014 (11) | −0.0168 (11) | −0.0148 (12) |
C13 | 0.0497 (14) | 0.0525 (14) | 0.0368 (12) | −0.0031 (11) | −0.0150 (10) | −0.0077 (11) |
C14 | 0.0586 (17) | 0.0563 (15) | 0.0467 (14) | 0.0002 (13) | −0.0127 (12) | −0.0119 (12) |
C15 | 0.0538 (17) | 0.078 (2) | 0.0535 (16) | 0.0075 (14) | −0.0104 (13) | −0.0096 (14) |
C16 | 0.0501 (17) | 0.098 (2) | 0.0545 (16) | −0.0111 (16) | −0.0135 (13) | −0.0125 (15) |
C17 | 0.068 (2) | 0.082 (2) | 0.084 (2) | −0.0144 (16) | −0.0267 (16) | −0.0314 (17) |
C18 | 0.0583 (17) | 0.0685 (18) | 0.0702 (18) | 0.0011 (13) | −0.0218 (14) | −0.0263 (14) |
C19 | 0.060 (2) | 0.172 (4) | 0.102 (3) | −0.024 (2) | −0.0240 (18) | −0.036 (3) |
C20 | 0.0685 (18) | 0.0412 (14) | 0.0731 (19) | 0.0053 (12) | −0.0335 (15) | −0.0167 (13) |
C21 | 0.094 (2) | 0.0552 (17) | 0.099 (2) | 0.0050 (16) | −0.057 (2) | −0.0218 (16) |
C22 | 0.095 (3) | 0.061 (2) | 0.150 (4) | −0.0058 (18) | −0.073 (3) | −0.023 (2) |
C23 | 0.091 (3) | 0.074 (2) | 0.138 (4) | −0.0194 (18) | −0.046 (3) | −0.004 (2) |
C24 | 0.088 (2) | 0.071 (2) | 0.091 (2) | −0.0188 (17) | −0.0256 (19) | −0.0032 (17) |
C25 | 0.0706 (19) | 0.0467 (15) | 0.0710 (19) | −0.0010 (13) | −0.0277 (15) | −0.0101 (13) |
C26 | 0.0733 (18) | 0.0481 (15) | 0.0552 (16) | 0.0035 (13) | −0.0242 (14) | −0.0097 (12) |
C27 | 0.100 (2) | 0.073 (2) | 0.0552 (18) | −0.0069 (17) | −0.0293 (16) | −0.0048 (14) |
C28 | 0.109 (3) | 0.078 (2) | 0.0612 (19) | −0.0026 (19) | −0.0468 (19) | −0.0121 (16) |
C29 | 0.085 (2) | 0.0659 (18) | 0.080 (2) | −0.0002 (15) | −0.0494 (18) | −0.0188 (16) |
C30 | 0.0643 (18) | 0.0634 (17) | 0.0626 (17) | 0.0032 (13) | −0.0243 (14) | −0.0140 (13) |
C31 | 0.0655 (17) | 0.0482 (14) | 0.0540 (16) | 0.0101 (12) | −0.0269 (13) | −0.0178 (12) |
C32 | 0.0537 (16) | 0.0665 (17) | 0.0410 (14) | −0.0012 (13) | −0.0074 (12) | −0.0013 (12) |
C33 | 0.0689 (19) | 0.082 (2) | 0.0523 (16) | −0.0077 (16) | −0.0127 (14) | −0.0023 (14) |
C34 | 0.119 (3) | 0.068 (2) | 0.0586 (19) | −0.018 (2) | −0.0142 (19) | −0.0022 (16) |
C35 | 0.118 (3) | 0.068 (2) | 0.064 (2) | 0.008 (2) | 0.002 (2) | 0.0051 (16) |
C36 | 0.070 (2) | 0.090 (3) | 0.095 (3) | 0.019 (2) | 0.0004 (19) | 0.015 (2) |
C37 | 0.0616 (19) | 0.078 (2) | 0.079 (2) | 0.0007 (16) | −0.0146 (15) | 0.0059 (16) |
C38 | 0.193 (4) | 0.084 (3) | 0.105 (3) | 0.034 (3) | 0.001 (3) | −0.006 (2) |
S1—O1 | 1.4173 (17) | C17—C18 | 1.375 (3) |
S1—O2 | 1.4262 (17) | C17—H17 | 0.9300 |
S1—N1 | 1.6662 (19) | C18—H18 | 0.9300 |
S1—C13 | 1.753 (2) | C19—H19A | 0.9600 |
S2—O3 | 1.418 (2) | C19—H19B | 0.9600 |
S2—O4 | 1.4213 (19) | C19—H19C | 0.9600 |
S2—N2 | 1.666 (2) | C20—C25 | 1.391 (4) |
S2—C32 | 1.744 (3) | C20—C21 | 1.395 (4) |
N1—C12 | 1.427 (3) | C21—C22 | 1.389 (5) |
N1—C1 | 1.433 (3) | C21—H21 | 0.9300 |
N2—C31 | 1.428 (3) | C22—C23 | 1.377 (5) |
N2—C20 | 1.436 (3) | C22—H22 | 0.9300 |
C1—C2 | 1.387 (3) | C23—C24 | 1.372 (4) |
C1—C6 | 1.400 (3) | C23—H23 | 0.9300 |
C2—C3 | 1.384 (3) | C24—C25 | 1.392 (4) |
C2—H2 | 0.9300 | C24—H24 | 0.9300 |
C3—C4 | 1.386 (4) | C25—C26 | 1.448 (4) |
C3—H3 | 0.9300 | C26—C27 | 1.385 (3) |
C4—C5 | 1.370 (4) | C26—C31 | 1.401 (3) |
C4—H4 | 0.9300 | C27—C28 | 1.371 (4) |
C5—C6 | 1.393 (3) | C27—H27 | 0.9300 |
C5—H5 | 0.9300 | C28—C29 | 1.383 (4) |
C6—C7 | 1.445 (3) | C28—H28 | 0.9300 |
C7—C12 | 1.394 (3) | C29—C30 | 1.389 (3) |
C7—C8 | 1.397 (3) | C29—H29 | 0.9300 |
C8—C9 | 1.370 (4) | C30—C31 | 1.381 (3) |
C8—H8 | 0.9300 | C30—H30 | 0.9300 |
C9—C10 | 1.382 (4) | C32—C37 | 1.383 (4) |
C9—H9 | 0.9300 | C32—C33 | 1.389 (4) |
C10—C11 | 1.379 (4) | C33—C34 | 1.375 (4) |
C10—H10 | 0.9300 | C33—H33 | 0.9300 |
C11—C12 | 1.386 (3) | C34—C35 | 1.370 (5) |
C11—H11 | 0.9300 | C34—H34 | 0.9300 |
C13—C14 | 1.384 (3) | C35—C36 | 1.379 (5) |
C13—C18 | 1.388 (3) | C35—C38 | 1.508 (4) |
C14—C15 | 1.371 (3) | C36—C37 | 1.380 (4) |
C14—H14 | 0.9300 | C36—H36 | 0.9300 |
C15—C16 | 1.381 (4) | C37—H37 | 0.9300 |
C15—H15 | 0.9300 | C38—H38A | 0.9600 |
C16—C17 | 1.385 (4) | C38—H38B | 0.9600 |
C16—C19 | 1.520 (4) | C38—H38C | 0.9600 |
O1—S1—O2 | 120.35 (11) | C17—C18—C13 | 118.5 (2) |
O1—S1—N1 | 106.28 (9) | C17—C18—H18 | 120.7 |
O2—S1—N1 | 106.14 (10) | C13—C18—H18 | 120.7 |
O1—S1—C13 | 108.45 (11) | C16—C19—H19A | 109.5 |
O2—S1—C13 | 109.03 (10) | C16—C19—H19B | 109.5 |
N1—S1—C13 | 105.61 (10) | H19A—C19—H19B | 109.5 |
O3—S2—O4 | 120.56 (13) | C16—C19—H19C | 109.5 |
O3—S2—N2 | 106.30 (12) | H19A—C19—H19C | 109.5 |
O4—S2—N2 | 105.98 (12) | H19B—C19—H19C | 109.5 |
O3—S2—C32 | 108.74 (13) | C25—C20—C21 | 121.4 (3) |
O4—S2—C32 | 109.30 (13) | C25—C20—N2 | 108.6 (2) |
N2—S2—C32 | 104.80 (10) | C21—C20—N2 | 129.9 (3) |
C12—N1—C1 | 107.79 (18) | C22—C21—C20 | 116.8 (3) |
C12—N1—S1 | 124.98 (15) | C22—C21—H21 | 121.6 |
C1—N1—S1 | 125.11 (16) | C20—C21—H21 | 121.6 |
C31—N2—C20 | 107.1 (2) | C23—C22—C21 | 122.2 (3) |
C31—N2—S2 | 122.54 (17) | C23—C22—H22 | 118.9 |
C20—N2—S2 | 125.59 (17) | C21—C22—H22 | 118.9 |
C2—C1—C6 | 121.6 (2) | C24—C23—C22 | 120.5 (3) |
C2—C1—N1 | 130.6 (2) | C24—C23—H23 | 119.7 |
C6—C1—N1 | 107.7 (2) | C22—C23—H23 | 119.7 |
C3—C2—C1 | 117.5 (2) | C23—C24—C25 | 119.0 (3) |
C3—C2—H2 | 121.3 | C23—C24—H24 | 120.5 |
C1—C2—H2 | 121.3 | C25—C24—H24 | 120.5 |
C2—C3—C4 | 121.6 (2) | C20—C25—C24 | 120.0 (3) |
C2—C3—H3 | 119.2 | C20—C25—C26 | 107.9 (2) |
C4—C3—H3 | 119.2 | C24—C25—C26 | 132.1 (3) |
C5—C4—C3 | 120.6 (2) | C27—C26—C31 | 119.5 (3) |
C5—C4—H4 | 119.7 | C27—C26—C25 | 132.6 (3) |
C3—C4—H4 | 119.7 | C31—C26—C25 | 107.8 (2) |
C4—C5—C6 | 119.4 (2) | C28—C27—C26 | 119.3 (3) |
C4—C5—H5 | 120.3 | C28—C27—H27 | 120.4 |
C6—C5—H5 | 120.3 | C26—C27—H27 | 120.4 |
C5—C6—C1 | 119.3 (2) | C27—C28—C29 | 120.6 (3) |
C5—C6—C7 | 132.6 (2) | C27—C28—H28 | 119.7 |
C1—C6—C7 | 108.1 (2) | C29—C28—H28 | 119.7 |
C12—C7—C8 | 120.0 (2) | C28—C29—C30 | 121.7 (3) |
C12—C7—C6 | 108.0 (2) | C28—C29—H29 | 119.2 |
C8—C7—C6 | 132.0 (2) | C30—C29—H29 | 119.2 |
C9—C8—C7 | 118.6 (3) | C31—C30—C29 | 117.1 (3) |
C9—C8—H8 | 120.7 | C31—C30—H30 | 121.4 |
C7—C8—H8 | 120.7 | C29—C30—H30 | 121.4 |
C8—C9—C10 | 120.7 (3) | C30—C31—C26 | 121.8 (2) |
C8—C9—H9 | 119.6 | C30—C31—N2 | 129.8 (2) |
C10—C9—H9 | 119.6 | C26—C31—N2 | 108.4 (2) |
C11—C10—C9 | 121.9 (3) | C37—C32—C33 | 120.1 (3) |
C11—C10—H10 | 119.1 | C37—C32—S2 | 119.4 (2) |
C9—C10—H10 | 119.1 | C33—C32—S2 | 120.5 (2) |
C10—C11—C12 | 117.5 (3) | C34—C33—C32 | 119.1 (3) |
C10—C11—H11 | 121.2 | C34—C33—H33 | 120.5 |
C12—C11—H11 | 121.2 | C32—C33—H33 | 120.5 |
C11—C12—C7 | 121.3 (2) | C35—C34—C33 | 122.0 (3) |
C11—C12—N1 | 130.5 (2) | C35—C34—H34 | 119.0 |
C7—C12—N1 | 108.25 (19) | C33—C34—H34 | 119.0 |
C14—C13—C18 | 120.3 (2) | C34—C35—C36 | 118.1 (3) |
C14—C13—S1 | 119.92 (18) | C34—C35—C38 | 121.5 (4) |
C18—C13—S1 | 119.78 (19) | C36—C35—C38 | 120.4 (4) |
C15—C14—C13 | 119.7 (2) | C35—C36—C37 | 121.7 (3) |
C15—C14—H14 | 120.2 | C35—C36—H36 | 119.2 |
C13—C14—H14 | 120.2 | C37—C36—H36 | 119.2 |
C14—C15—C16 | 121.5 (2) | C36—C37—C32 | 119.1 (3) |
C14—C15—H15 | 119.3 | C36—C37—H37 | 120.5 |
C16—C15—H15 | 119.3 | C32—C37—H37 | 120.5 |
C15—C16—C17 | 117.8 (3) | C35—C38—H38A | 109.5 |
C15—C16—C19 | 120.9 (3) | C35—C38—H38B | 109.5 |
C17—C16—C19 | 121.3 (3) | H38A—C38—H38B | 109.5 |
C18—C17—C16 | 122.2 (3) | C35—C38—H38C | 109.5 |
C18—C17—H17 | 118.9 | H38A—C38—H38C | 109.5 |
C16—C17—H17 | 118.9 | H38B—C38—H38C | 109.5 |
O1—S1—N1—C12 | −165.59 (17) | C14—C15—C16—C19 | −179.8 (3) |
O2—S1—N1—C12 | −36.3 (2) | C15—C16—C17—C18 | −0.9 (4) |
C13—S1—N1—C12 | 79.33 (19) | C19—C16—C17—C18 | 179.3 (3) |
O1—S1—N1—C1 | 33.0 (2) | C16—C17—C18—C13 | 0.3 (4) |
O2—S1—N1—C1 | 162.26 (18) | C14—C13—C18—C17 | 0.9 (4) |
C13—S1—N1—C1 | −82.1 (2) | S1—C13—C18—C17 | −179.0 (2) |
O3—S2—N2—C31 | −46.0 (2) | C31—N2—C20—C25 | 3.3 (2) |
O4—S2—N2—C31 | −175.36 (18) | S2—N2—C20—C25 | 159.22 (17) |
C32—S2—N2—C31 | 69.1 (2) | C31—N2—C20—C21 | −178.4 (2) |
O3—S2—N2—C20 | 161.60 (18) | S2—N2—C20—C21 | −22.5 (3) |
O4—S2—N2—C20 | 32.2 (2) | C25—C20—C21—C22 | −0.4 (4) |
C32—S2—N2—C20 | −83.4 (2) | N2—C20—C21—C22 | −178.4 (2) |
C12—N1—C1—C2 | −178.8 (2) | C20—C21—C22—C23 | 0.1 (4) |
S1—N1—C1—C2 | −14.8 (3) | C21—C22—C23—C24 | 0.2 (5) |
C12—N1—C1—C6 | 2.8 (2) | C22—C23—C24—C25 | −0.1 (5) |
S1—N1—C1—C6 | 166.91 (16) | C21—C20—C25—C24 | 0.4 (4) |
C6—C1—C2—C3 | 1.1 (3) | N2—C20—C25—C24 | 178.9 (2) |
N1—C1—C2—C3 | −177.0 (2) | C21—C20—C25—C26 | 179.9 (2) |
C1—C2—C3—C4 | −0.1 (4) | N2—C20—C25—C26 | −1.7 (3) |
C2—C3—C4—C5 | −0.6 (4) | C23—C24—C25—C20 | −0.2 (4) |
C3—C4—C5—C6 | 0.4 (4) | C23—C24—C25—C26 | −179.4 (3) |
C4—C5—C6—C1 | 0.5 (4) | C20—C25—C26—C27 | −180.0 (3) |
C4—C5—C6—C7 | −179.8 (2) | C24—C25—C26—C27 | −0.6 (5) |
C2—C1—C6—C5 | −1.3 (4) | C20—C25—C26—C31 | −0.6 (3) |
N1—C1—C6—C5 | 177.2 (2) | C24—C25—C26—C31 | 178.8 (3) |
C2—C1—C6—C7 | 178.9 (2) | C31—C26—C27—C28 | −2.0 (4) |
N1—C1—C6—C7 | −2.6 (2) | C25—C26—C27—C28 | 177.3 (3) |
C5—C6—C7—C12 | −178.4 (3) | C26—C27—C28—C29 | 0.8 (4) |
C1—C6—C7—C12 | 1.3 (3) | C27—C28—C29—C30 | 1.0 (4) |
C5—C6—C7—C8 | 0.5 (4) | C28—C29—C30—C31 | −1.5 (4) |
C1—C6—C7—C8 | −179.8 (3) | C29—C30—C31—C26 | 0.2 (4) |
C12—C7—C8—C9 | 0.9 (4) | C29—C30—C31—N2 | 179.5 (2) |
C6—C7—C8—C9 | −177.9 (3) | C27—C26—C31—C30 | 1.5 (4) |
C7—C8—C9—C10 | −0.6 (4) | C25—C26—C31—C30 | −177.9 (2) |
C8—C9—C10—C11 | −0.3 (5) | C27—C26—C31—N2 | −177.9 (2) |
C9—C10—C11—C12 | 0.9 (4) | C25—C26—C31—N2 | 2.7 (3) |
C10—C11—C12—C7 | −0.6 (3) | C20—N2—C31—C30 | 177.0 (2) |
C10—C11—C12—N1 | 177.3 (2) | S2—N2—C31—C30 | 20.2 (3) |
C8—C7—C12—C11 | −0.2 (3) | C20—N2—C31—C26 | −3.7 (2) |
C6—C7—C12—C11 | 178.8 (2) | S2—N2—C31—C26 | −160.48 (17) |
C8—C7—C12—N1 | −178.6 (2) | O3—S2—C32—C37 | −163.0 (2) |
C6—C7—C12—N1 | 0.5 (2) | O4—S2—C32—C37 | −29.6 (2) |
C1—N1—C12—C11 | 179.8 (2) | N2—S2—C32—C37 | 83.6 (2) |
S1—N1—C12—C11 | 15.7 (3) | O3—S2—C32—C33 | 19.1 (2) |
C1—N1—C12—C7 | −2.0 (2) | O4—S2—C32—C33 | 152.5 (2) |
S1—N1—C12—C7 | −166.12 (16) | N2—S2—C32—C33 | −94.3 (2) |
O1—S1—C13—C14 | −22.5 (2) | C37—C32—C33—C34 | −0.6 (4) |
O2—S1—C13—C14 | −155.24 (18) | S2—C32—C33—C34 | 177.27 (19) |
N1—S1—C13—C14 | 91.08 (19) | C32—C33—C34—C35 | 0.4 (4) |
O1—S1—C13—C18 | 157.31 (19) | C33—C34—C35—C36 | 0.3 (5) |
O2—S1—C13—C18 | 24.6 (2) | C33—C34—C35—C38 | −179.1 (3) |
N1—S1—C13—C18 | −89.1 (2) | C34—C35—C36—C37 | −0.8 (5) |
C18—C13—C14—C15 | −1.3 (3) | C38—C35—C36—C37 | 178.6 (3) |
S1—C13—C14—C15 | 178.49 (18) | C35—C36—C37—C32 | 0.6 (5) |
C13—C14—C15—C16 | 0.7 (4) | C33—C32—C37—C36 | 0.1 (4) |
C14—C15—C16—C17 | 0.4 (4) | S2—C32—C37—C36 | −177.8 (2) |