Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807006174/hj3029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807006174/hj3029Isup2.hkl |
CCDC reference: 641535
Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C32H26N2S2 | F(000) = 1056 |
Mr = 502.67 | Dx = 1.29 Mg m−3 |
Monoclinic, P21/a | Mo Kα radiation, λ = 0.71073 Å |
a = 11.9699 (13) Å | Cell parameters from 2000 reflections |
b = 12.3375 (15) Å | θ = 2.0–26.8° |
c = 17.8027 (18) Å | µ = 0.23 mm−1 |
β = 100.192 (8)° | T = 298 K |
V = 2587.6 (5) Å3 | Prism, pale yellow |
Z = 4 | 0.6 × 0.55 × 0.3 mm |
Stoe IPDS-II diffractometer | 5408 independent reflections |
Radiation source: fine-focus sealed tube | 4680 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.041 |
Detector resolution: 0.15 mm pixels mm-1 | θmax = 26.8°, θmin = 2.0° |
rotation method scans | h = −15→15 |
Absorption correction: numerical shape of crystal determined optically | k = −13→15 |
Tmin = 0.865, Tmax = 0.945 | l = −20→22 |
12356 measured reflections |
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) = 0.121 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0553P)2 + 0.7891P] where P = (Fo2 + 2Fc2)/3 |
5408 reflections | (Δ/σ)max = 0.024 |
327 parameters | Δρmax = 0.23 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Experimental. 1HNMR (CDCl3) δ 3.40 (s, 3H), 3.83 (s, 3H), 5.30 (s, 1H), 5.50 (s, 1H), 6.21 (d, J=8.0 Hz, 1H), 6.48 (d, J=7.9 Hz, 1H), 6.60 (d, J=7.8 Hz, 1H), 6.70 (t, J=7.6 Hz, 1H), 6.78 (t, J=7.6 Hz, 1H), 6.84 (d, J=7.5 Hz, 2H), 7.01–7.05 (m, 3H), 7.12–7.21 (m, 4H), 7.28 (d, J=7.8 Hz, 1H), 7.33 (d, J=8.2 Hz, 1H), 7.54 (d, J=7.6 Hz, 1H), 7.93 (d, J=7.5 Hz, 1H); 13CNMR (CDCl3) δ 30.5(CH3), 31.4(CH3), 52.3(CH), 55.6(CH), 66.4(C), 108.4(CH), 108.8(C), 109.1(CH), 119.3(CH), 119.9(CH), 121.1(CH), 123.5(CH), 126.9(CH), 127.1(CH), 127.5(CH), 127.8(C), 127.9(2CH), 128.8(CH), 128.9(2CH), 129.9(2CH), 130.7(CH), 130.9(C), 131.6(CH), 131.9(C), 135.2(C), 137.7(C), 138.1(C), 146.3(C), 204.3(C). |
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. The structure was solved by direct methods. 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 | ||
C1 | 0.62628 (14) | 0.58810 (17) | 0.89010 (13) | 0.0581 (5) | |
H1C | 0.6598 | 0.5544 | 0.9374 | 0.07* | |
H1B | 0.6603 | 0.6579 | 0.8863 | 0.07* | |
H1A | 0.6388 | 0.5434 | 0.8482 | 0.07* | |
C2 | 0.45345 (14) | 0.62980 (13) | 0.94784 (10) | 0.0428 (4) | |
C3 | 0.50160 (16) | 0.65208 (16) | 1.02351 (11) | 0.0532 (4) | |
H3 | 0.5795 | 0.6465 | 1.0405 | 0.064* | |
C4 | 0.42985 (19) | 0.68252 (16) | 1.07190 (11) | 0.0593 (5) | |
H4 | 0.4598 | 0.6988 | 1.1225 | 0.071* | |
C5 | 0.31249 (18) | 0.68959 (16) | 1.04674 (11) | 0.0553 (4) | |
H5 | 0.2661 | 0.7113 | 1.0807 | 0.066* | |
C6 | 0.26445 (15) | 0.66507 (14) | 0.97264 (10) | 0.0460 (4) | |
H6 | 0.1862 | 0.669 | 0.9568 | 0.055* | |
C7 | 0.33485 (13) | 0.63410 (12) | 0.92128 (9) | 0.0398 (3) | |
C8 | 0.31615 (12) | 0.60537 (12) | 0.84153 (9) | 0.0379 (3) | |
C9 | 0.42192 (13) | 0.58723 (13) | 0.82413 (10) | 0.0407 (3) | |
C10 | 0.31876 (13) | 0.58031 (14) | 0.67646 (10) | 0.0420 (4) | |
H10 | 0.3102 | 0.6592 | 0.6728 | 0.05* | |
C11 | 0.32798 (14) | 0.53964 (16) | 0.59740 (10) | 0.0476 (4) | |
C12 | 0.33181 (19) | 0.43066 (19) | 0.57931 (13) | 0.0639 (5) | |
H12 | 0.3267 | 0.3787 | 0.6164 | 0.077* | |
C13 | 0.3432 (2) | 0.3980 (3) | 0.50635 (14) | 0.0784 (7) | |
H13 | 0.3444 | 0.3246 | 0.4948 | 0.094* | |
C14 | 0.3524 (2) | 0.4733 (3) | 0.45163 (13) | 0.0850 (9) | |
H14 | 0.3609 | 0.4513 | 0.403 | 0.102* | |
C15 | 0.3493 (2) | 0.5809 (3) | 0.46858 (13) | 0.0839 (8) | |
H15 | 0.3553 | 0.632 | 0.4311 | 0.101* | |
C16 | 0.33711 (16) | 0.6153 (2) | 0.54134 (12) | 0.0632 (5) | |
H16 | 0.3351 | 0.6889 | 0.5522 | 0.076* | |
C17 | 0.21727 (12) | 0.53655 (13) | 0.71157 (9) | 0.0377 (3) | |
C18 | 0.20667 (12) | 0.60497 (13) | 0.78491 (9) | 0.0370 (3) | |
H18 | 0.1932 | 0.6801 | 0.7678 | 0.044* | |
C19 | 0.10447 (12) | 0.57187 (13) | 0.81991 (9) | 0.0383 (3) | |
C20 | 0.10713 (15) | 0.48337 (14) | 0.86834 (10) | 0.0463 (4) | |
H20 | 0.172 | 0.4405 | 0.8783 | 0.056* | |
C21 | 0.01470 (17) | 0.45794 (16) | 0.90200 (13) | 0.0573 (5) | |
H21 | 0.0178 | 0.3985 | 0.9344 | 0.069* | |
C22 | −0.08206 (17) | 0.52100 (19) | 0.88744 (15) | 0.0683 (6) | |
H22 | −0.1441 | 0.5046 | 0.9103 | 0.082* | |
C23 | −0.08624 (16) | 0.60836 (19) | 0.83886 (15) | 0.0671 (6) | |
H23 | −0.1517 | 0.6504 | 0.8284 | 0.08* | |
C24 | 0.00646 (14) | 0.63390 (15) | 0.80558 (11) | 0.0497 (4) | |
H24 | 0.003 | 0.6934 | 0.7732 | 0.06* | |
C25 | 0.21476 (13) | 0.41578 (13) | 0.72498 (9) | 0.0404 (3) | |
C26 | 0.29154 (16) | 0.34506 (15) | 0.76711 (10) | 0.0490 (4) | |
H26 | 0.3597 | 0.3708 | 0.7946 | 0.059* | |
C27 | 0.2655 (2) | 0.23537 (17) | 0.76770 (13) | 0.0678 (6) | |
H27 | 0.3178 | 0.1873 | 0.7945 | 0.081* | |
C28 | 0.1645 (3) | 0.1972 (2) | 0.72960 (15) | 0.0799 (7) | |
H28 | 0.1486 | 0.1236 | 0.7316 | 0.096* | |
C29 | 0.0853 (2) | 0.2653 (2) | 0.68811 (15) | 0.0764 (7) | |
H29 | 0.0158 | 0.2392 | 0.6628 | 0.092* | |
C30 | 0.11357 (16) | 0.37518 (17) | 0.68555 (10) | 0.0526 (4) | |
C31 | −0.0617 (2) | 0.4452 (3) | 0.59926 (18) | 0.1038 (11) | |
H31A | −0.1099 | 0.4105 | 0.6297 | 0.125* | |
H31B | −0.0566 | 0.4009 | 0.5556 | 0.125* | |
H31C | −0.0928 | 0.5146 | 0.5825 | 0.125* | |
C32 | 0.10721 (14) | 0.55550 (17) | 0.65434 (10) | 0.0499 (4) | |
N1 | 0.50500 (11) | 0.60107 (12) | 0.88774 (9) | 0.0445 (3) | |
N2 | 0.05138 (13) | 0.45966 (17) | 0.64472 (9) | 0.0605 (4) | |
S1 | 0.45664 (3) | 0.55353 (4) | 0.73608 (3) | 0.04850 (14) | |
S2 | 0.06450 (5) | 0.67203 (6) | 0.61461 (3) | 0.0765 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0306 (8) | 0.0587 (11) | 0.0819 (14) | −0.0029 (7) | 0.0015 (8) | −0.0088 (10) |
C2 | 0.0426 (8) | 0.0349 (8) | 0.0487 (9) | −0.0023 (6) | 0.0020 (7) | 0.0001 (7) |
C3 | 0.0514 (10) | 0.0484 (10) | 0.0538 (10) | −0.0047 (8) | −0.0067 (8) | 0.0002 (8) |
C4 | 0.0740 (13) | 0.0547 (11) | 0.0441 (10) | −0.0050 (9) | −0.0032 (9) | −0.0033 (8) |
C5 | 0.0704 (12) | 0.0525 (10) | 0.0442 (9) | 0.0045 (9) | 0.0136 (9) | −0.0024 (8) |
C6 | 0.0499 (9) | 0.0434 (9) | 0.0452 (9) | 0.0032 (7) | 0.0100 (7) | −0.0006 (7) |
C7 | 0.0405 (8) | 0.0338 (7) | 0.0441 (8) | 0.0003 (6) | 0.0052 (6) | 0.0003 (6) |
C8 | 0.0331 (7) | 0.0374 (8) | 0.0435 (8) | −0.0007 (6) | 0.0075 (6) | −0.0020 (6) |
C9 | 0.0332 (7) | 0.0394 (8) | 0.0494 (9) | −0.0021 (6) | 0.0073 (6) | −0.0032 (7) |
C10 | 0.0385 (8) | 0.0428 (8) | 0.0468 (9) | 0.0017 (6) | 0.0132 (7) | 0.0039 (7) |
C11 | 0.0362 (8) | 0.0645 (11) | 0.0438 (9) | 0.0009 (7) | 0.0114 (7) | 0.0042 (8) |
C12 | 0.0691 (13) | 0.0704 (13) | 0.0582 (12) | 0.0044 (10) | 0.0278 (10) | −0.0053 (10) |
C13 | 0.0678 (13) | 0.107 (2) | 0.0646 (14) | −0.0017 (13) | 0.0229 (11) | −0.0247 (14) |
C14 | 0.0557 (12) | 0.155 (3) | 0.0446 (11) | −0.0051 (15) | 0.0106 (9) | −0.0158 (15) |
C15 | 0.0640 (14) | 0.141 (3) | 0.0470 (12) | −0.0063 (15) | 0.0108 (10) | 0.0245 (15) |
C16 | 0.0499 (10) | 0.0876 (15) | 0.0529 (11) | −0.0035 (10) | 0.0111 (9) | 0.0164 (11) |
C17 | 0.0308 (7) | 0.0444 (8) | 0.0381 (8) | 0.0022 (6) | 0.0066 (6) | 0.0029 (6) |
C18 | 0.0314 (7) | 0.0373 (8) | 0.0427 (8) | 0.0028 (6) | 0.0079 (6) | 0.0009 (6) |
C19 | 0.0329 (7) | 0.0401 (8) | 0.0429 (8) | 0.0008 (6) | 0.0092 (6) | −0.0056 (6) |
C20 | 0.0449 (9) | 0.0442 (9) | 0.0530 (10) | 0.0048 (7) | 0.0174 (7) | 0.0002 (7) |
C21 | 0.0612 (11) | 0.0490 (10) | 0.0684 (12) | −0.0042 (8) | 0.0299 (10) | 0.0010 (9) |
C22 | 0.0497 (10) | 0.0675 (13) | 0.0976 (17) | −0.0027 (9) | 0.0402 (11) | −0.0020 (12) |
C23 | 0.0408 (9) | 0.0679 (13) | 0.0981 (17) | 0.0126 (9) | 0.0275 (10) | 0.0020 (12) |
C24 | 0.0388 (8) | 0.0503 (10) | 0.0621 (11) | 0.0079 (7) | 0.0143 (8) | 0.0006 (8) |
C25 | 0.0420 (8) | 0.0444 (8) | 0.0374 (8) | −0.0045 (6) | 0.0139 (6) | −0.0049 (7) |
C26 | 0.0612 (10) | 0.0443 (9) | 0.0438 (9) | 0.0034 (8) | 0.0154 (8) | 0.0024 (7) |
C27 | 0.1074 (18) | 0.0459 (10) | 0.0577 (12) | 0.0020 (11) | 0.0350 (12) | 0.0048 (9) |
C28 | 0.123 (2) | 0.0512 (12) | 0.0748 (15) | −0.0232 (14) | 0.0435 (16) | −0.0077 (11) |
C29 | 0.0808 (15) | 0.0822 (16) | 0.0712 (14) | −0.0407 (14) | 0.0267 (12) | −0.0280 (13) |
C30 | 0.0497 (9) | 0.0661 (12) | 0.0442 (9) | −0.0149 (9) | 0.0143 (8) | −0.0139 (8) |
C31 | 0.0527 (13) | 0.160 (3) | 0.0864 (19) | −0.0185 (16) | −0.0201 (13) | −0.016 (2) |
C32 | 0.0371 (8) | 0.0762 (13) | 0.0365 (8) | 0.0091 (8) | 0.0066 (7) | 0.0030 (8) |
N1 | 0.0309 (6) | 0.0446 (8) | 0.0558 (8) | −0.0025 (5) | 0.0018 (6) | −0.0029 (6) |
N2 | 0.0388 (8) | 0.0913 (13) | 0.0484 (9) | −0.0087 (8) | −0.0005 (7) | −0.0122 (9) |
S1 | 0.0327 (2) | 0.0608 (3) | 0.0541 (3) | 0.00021 (17) | 0.01321 (17) | −0.0086 (2) |
S2 | 0.0651 (3) | 0.1012 (5) | 0.0623 (3) | 0.0352 (3) | 0.0088 (3) | 0.0294 (3) |
C1—N1 | 1.454 (2) | C16—H16 | 0.93 |
C1—H1C | 0.96 | C17—C25 | 1.510 (2) |
C1—H1B | 0.96 | C17—C32 | 1.534 (2) |
C1—H1A | 0.96 | C17—C18 | 1.579 (2) |
C2—N1 | 1.373 (2) | C18—C19 | 1.524 (2) |
C2—C3 | 1.396 (3) | C18—H18 | 0.98 |
C2—C7 | 1.416 (2) | C19—C24 | 1.386 (2) |
C3—C4 | 1.372 (3) | C19—C20 | 1.388 (2) |
C3—H3 | 0.93 | C20—C21 | 1.384 (2) |
C4—C5 | 1.400 (3) | C20—H20 | 0.93 |
C4—H4 | 0.93 | C21—C22 | 1.381 (3) |
C5—C6 | 1.376 (3) | C21—H21 | 0.93 |
C5—H5 | 0.93 | C22—C23 | 1.377 (3) |
C6—C7 | 1.402 (2) | C22—H22 | 0.93 |
C6—H6 | 0.93 | C23—C24 | 1.384 (3) |
C7—C8 | 1.442 (2) | C23—H23 | 0.93 |
C8—C9 | 1.374 (2) | C24—H24 | 0.93 |
C8—C18 | 1.505 (2) | C25—C30 | 1.382 (2) |
C9—N1 | 1.379 (2) | C25—C26 | 1.387 (2) |
C9—S1 | 1.7416 (17) | C26—C27 | 1.389 (3) |
C10—C11 | 1.517 (2) | C26—H26 | 0.93 |
C10—C17 | 1.558 (2) | C27—C28 | 1.361 (4) |
C10—S1 | 1.8275 (17) | C27—H27 | 0.93 |
C10—H10 | 0.98 | C28—C29 | 1.379 (4) |
C11—C16 | 1.385 (3) | C28—H28 | 0.93 |
C11—C12 | 1.385 (3) | C29—C30 | 1.400 (3) |
C12—C13 | 1.389 (3) | C29—H29 | 0.93 |
C12—H12 | 0.93 | C30—N2 | 1.406 (3) |
C13—C14 | 1.364 (4) | C31—N2 | 1.460 (3) |
C13—H13 | 0.93 | C31—H31A | 0.96 |
C14—C15 | 1.363 (4) | C31—H31B | 0.96 |
C14—H14 | 0.93 | C31—H31C | 0.96 |
C15—C16 | 1.395 (4) | C32—N2 | 1.354 (3) |
C15—H15 | 0.93 | C32—S2 | 1.643 (2) |
N1—C1—H1C | 109.5 | C10—C17—C18 | 109.21 (13) |
N1—C1—H1B | 109.5 | C8—C18—C19 | 113.20 (13) |
H1C—C1—H1B | 109.5 | C8—C18—C17 | 111.57 (12) |
N1—C1—H1A | 109.5 | C19—C18—C17 | 112.50 (12) |
H1C—C1—H1A | 109.5 | C8—C18—H18 | 106.3 |
H1B—C1—H1A | 109.5 | C19—C18—H18 | 106.3 |
N1—C2—C3 | 129.59 (16) | C17—C18—H18 | 106.3 |
N1—C2—C7 | 108.17 (14) | C24—C19—C20 | 118.31 (15) |
C3—C2—C7 | 122.24 (17) | C24—C19—C18 | 119.44 (15) |
C4—C3—C2 | 117.55 (17) | C20—C19—C18 | 122.21 (14) |
C4—C3—H3 | 121.2 | C21—C20—C19 | 120.99 (16) |
C2—C3—H3 | 121.2 | C21—C20—H20 | 119.5 |
C3—C4—C5 | 121.36 (18) | C19—C20—H20 | 119.5 |
C3—C4—H4 | 119.3 | C22—C21—C20 | 119.94 (19) |
C5—C4—H4 | 119.3 | C22—C21—H21 | 120 |
C6—C5—C4 | 121.23 (18) | C20—C21—H21 | 120 |
C6—C5—H5 | 119.4 | C23—C22—C21 | 119.65 (18) |
C4—C5—H5 | 119.4 | C23—C22—H22 | 120.2 |
C5—C6—C7 | 119.19 (17) | C21—C22—H22 | 120.2 |
C5—C6—H6 | 120.4 | C22—C23—C24 | 120.29 (18) |
C7—C6—H6 | 120.4 | C22—C23—H23 | 119.9 |
C6—C7—C2 | 118.39 (15) | C24—C23—H23 | 119.9 |
C6—C7—C8 | 134.65 (15) | C23—C24—C19 | 120.82 (18) |
C2—C7—C8 | 106.94 (14) | C23—C24—H24 | 119.6 |
C9—C8—C7 | 105.87 (14) | C19—C24—H24 | 119.6 |
C9—C8—C18 | 125.19 (14) | C30—C25—C26 | 118.94 (17) |
C7—C8—C18 | 128.70 (13) | C30—C25—C17 | 108.51 (15) |
C8—C9—N1 | 110.74 (15) | C26—C25—C17 | 132.55 (15) |
C8—C9—S1 | 128.17 (13) | C25—C26—C27 | 119.3 (2) |
N1—C9—S1 | 121.09 (12) | C25—C26—H26 | 120.4 |
C11—C10—C17 | 116.60 (14) | C27—C26—H26 | 120.4 |
C11—C10—S1 | 105.83 (11) | C28—C27—C26 | 120.9 (2) |
C17—C10—S1 | 113.11 (11) | C28—C27—H27 | 119.5 |
C11—C10—H10 | 106.9 | C26—C27—H27 | 119.5 |
C17—C10—H10 | 106.9 | C27—C28—C29 | 121.5 (2) |
S1—C10—H10 | 106.9 | C27—C28—H28 | 119.3 |
C16—C11—C12 | 118.46 (19) | C29—C28—H28 | 119.3 |
C16—C11—C10 | 118.29 (19) | C28—C29—C30 | 117.4 (2) |
C12—C11—C10 | 123.21 (17) | C28—C29—H29 | 121.3 |
C11—C12—C13 | 120.7 (2) | C30—C29—H29 | 121.3 |
C11—C12—H12 | 119.6 | C25—C30—C29 | 122.0 (2) |
C13—C12—H12 | 119.6 | C25—C30—N2 | 109.28 (17) |
C14—C13—C12 | 120.3 (3) | C29—C30—N2 | 128.72 (19) |
C14—C13—H13 | 119.9 | N2—C31—H31A | 109.5 |
C12—C13—H13 | 119.9 | N2—C31—H31B | 109.5 |
C15—C14—C13 | 119.7 (2) | H31A—C31—H31B | 109.5 |
C15—C14—H14 | 120.1 | N2—C31—H31C | 109.5 |
C13—C14—H14 | 120.1 | H31A—C31—H31C | 109.5 |
C14—C15—C16 | 120.9 (2) | H31B—C31—H31C | 109.5 |
C14—C15—H15 | 119.6 | N2—C32—C17 | 107.30 (16) |
C16—C15—H15 | 119.6 | N2—C32—S2 | 126.91 (14) |
C11—C16—C15 | 119.9 (3) | C17—C32—S2 | 125.76 (15) |
C11—C16—H16 | 120 | C2—N1—C9 | 108.28 (13) |
C15—C16—H16 | 120 | C2—N1—C1 | 126.16 (15) |
C25—C17—C32 | 102.51 (14) | C9—N1—C1 | 125.56 (16) |
C25—C17—C10 | 116.37 (13) | C32—N2—C30 | 112.19 (14) |
C32—C17—C10 | 108.64 (13) | C32—N2—C31 | 124.4 (2) |
C25—C17—C18 | 112.96 (13) | C30—N2—C31 | 123.4 (2) |
C32—C17—C18 | 106.41 (12) | C9—S1—C10 | 98.33 (7) |
N1—C2—C3—C4 | 177.99 (18) | C24—C19—C20—C21 | −0.5 (3) |
C7—C2—C3—C4 | −2.2 (3) | C18—C19—C20—C21 | 177.13 (17) |
C2—C3—C4—C5 | 0.9 (3) | C19—C20—C21—C22 | 0.1 (3) |
C3—C4—C5—C6 | 0.7 (3) | C20—C21—C22—C23 | 0.6 (4) |
C4—C5—C6—C7 | −1.0 (3) | C21—C22—C23—C24 | −0.9 (4) |
C5—C6—C7—C2 | −0.3 (2) | C22—C23—C24—C19 | 0.5 (3) |
C5—C6—C7—C8 | −178.61 (18) | C20—C19—C24—C23 | 0.1 (3) |
N1—C2—C7—C6 | −178.20 (14) | C18—C19—C24—C23 | −177.51 (18) |
C3—C2—C7—C6 | 2.0 (2) | C32—C17—C25—C30 | −4.10 (16) |
N1—C2—C7—C8 | 0.53 (18) | C10—C17—C25—C30 | −122.49 (15) |
C3—C2—C7—C8 | −179.30 (16) | C18—C17—C25—C30 | 110.00 (15) |
C6—C7—C8—C9 | 177.57 (18) | C32—C17—C25—C26 | 175.90 (17) |
C2—C7—C8—C9 | −0.87 (18) | C10—C17—C25—C26 | 57.5 (2) |
C6—C7—C8—C18 | 3.1 (3) | C18—C17—C25—C26 | −70.0 (2) |
C2—C7—C8—C18 | −175.29 (15) | C30—C25—C26—C27 | 0.9 (3) |
C7—C8—C9—N1 | 0.90 (18) | C17—C25—C26—C27 | −179.12 (17) |
C18—C8—C9—N1 | 175.58 (14) | C25—C26—C27—C28 | −2.1 (3) |
C7—C8—C9—S1 | −178.01 (13) | C26—C27—C28—C29 | 1.1 (3) |
C18—C8—C9—S1 | −3.3 (3) | C27—C28—C29—C30 | 1.1 (3) |
C17—C10—C11—C16 | 127.30 (17) | C26—C25—C30—C29 | 1.3 (3) |
S1—C10—C11—C16 | −105.96 (16) | C17—C25—C30—C29 | −178.66 (17) |
C17—C10—C11—C12 | −55.1 (2) | C26—C25—C30—N2 | −177.65 (15) |
S1—C10—C11—C12 | 71.6 (2) | C17—C25—C30—N2 | 2.36 (19) |
C16—C11—C12—C13 | −0.8 (3) | C28—C29—C30—C25 | −2.3 (3) |
C10—C11—C12—C13 | −178.37 (19) | C28—C29—C30—N2 | 176.4 (2) |
C11—C12—C13—C14 | 1.0 (4) | C25—C17—C32—N2 | 4.48 (17) |
C12—C13—C14—C15 | −0.7 (4) | C10—C17—C32—N2 | 128.19 (15) |
C13—C14—C15—C16 | 0.2 (4) | C18—C17—C32—N2 | −114.34 (15) |
C12—C11—C16—C15 | 0.3 (3) | C25—C17—C32—S2 | −177.20 (13) |
C10—C11—C16—C15 | 178.02 (18) | C10—C17—C32—S2 | −53.50 (19) |
C14—C15—C16—C11 | 0.0 (3) | C18—C17—C32—S2 | 63.98 (17) |
C11—C10—C17—C25 | 62.35 (19) | C3—C2—N1—C9 | 179.83 (17) |
S1—C10—C17—C25 | −60.70 (17) | C7—C2—N1—C9 | 0.01 (18) |
C11—C10—C17—C32 | −52.64 (19) | C3—C2—N1—C1 | −0.6 (3) |
S1—C10—C17—C32 | −175.68 (12) | C7—C2—N1—C1 | 179.58 (16) |
C11—C10—C17—C18 | −168.32 (14) | C8—C9—N1—C2 | −0.59 (19) |
S1—C10—C17—C18 | 68.64 (14) | S1—C9—N1—C2 | 178.41 (12) |
C9—C8—C18—C19 | 151.50 (15) | C8—C9—N1—C1 | 179.84 (16) |
C7—C8—C18—C19 | −35.1 (2) | S1—C9—N1—C1 | −1.2 (2) |
C9—C8—C18—C17 | 23.4 (2) | C17—C32—N2—C30 | −3.4 (2) |
C7—C8—C18—C17 | −163.19 (15) | S2—C32—N2—C30 | 178.31 (13) |
C25—C17—C18—C8 | 76.02 (16) | C17—C32—N2—C31 | 174.9 (2) |
C32—C17—C18—C8 | −172.25 (13) | S2—C32—N2—C31 | −3.4 (3) |
C10—C17—C18—C8 | −55.15 (16) | C25—C30—N2—C32 | 0.7 (2) |
C25—C17—C18—C19 | −52.46 (17) | C29—C30—N2—C32 | −178.17 (19) |
C32—C17—C18—C19 | 59.26 (17) | C25—C30—N2—C31 | −177.6 (2) |
C10—C17—C18—C19 | 176.36 (13) | C29—C30—N2—C31 | 3.5 (3) |
C8—C18—C19—C24 | 132.04 (16) | C8—C9—S1—C10 | 11.79 (17) |
C17—C18—C19—C24 | −100.33 (18) | N1—C9—S1—C10 | −167.01 (14) |
C8—C18—C19—C20 | −45.5 (2) | C11—C10—S1—C9 | −172.11 (12) |
C17—C18—C19—C20 | 82.11 (19) | C17—C10—S1—C9 | −43.28 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1A···S1 | 0.96 | 2.69 | 3.139 (2) | 109 |
C10—H10···S2 | 0.98 | 2.95 | 3.251 (2) | 99 |
C18—H18···S2 | 0.98 | 2.89 | 3.309 (2) | 107 |
C26—H26···S1 | 0.93 | 2.82 | 3.348 (2) | 117 |
C31—H31C···S2 | 0.96 | 2.70 | 3.169 (4) | 111 |