Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014298/ci2319sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014298/ci2319Isup2.hkl |
CCDC reference: 647146
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
C28H29BrN2O2S2 | F(000) = 1176 |
Mr = 569.56 | Dx = 1.437 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3174 reflections |
a = 14.7207 (8) Å | θ = 2.1–25.0° |
b = 9.1692 (5) Å | µ = 1.75 mm−1 |
c = 20.6819 (11) Å | T = 293 K |
β = 109.461 (1)° | Block, colourless |
V = 2632.1 (2) Å3 | 0.25 × 0.24 × 0.22 mm |
Z = 4 |
Bruker SMART APEX CCD area-detector diffractometer | 4428 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 28.0°, θmin = 2.1° |
ω scans | h = −19→19 |
29550 measured reflections | k = −12→11 |
6207 independent reflections | l = −26→27 |
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.130 | H-atom parameters constrained |
S = 0.97 | w = 1/[σ2(Fo2) + (0.0721P)2 + 1.0141P] where P = (Fo2 + 2Fc2)/3 |
6207 reflections | (Δ/σ)max = 0.002 |
317 parameters | Δρmax = 0.80 e Å−3 |
0 restraints | Δρmin = −0.53 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 | ||
C1 | 0.10842 (17) | 0.1413 (3) | 0.69464 (14) | 0.0449 (6) | |
H1A | 0.0945 | 0.1805 | 0.7339 | 0.054* | |
H1B | 0.0498 | 0.1418 | 0.6552 | 0.054* | |
C2 | 0.18766 (17) | 0.2280 (3) | 0.68034 (12) | 0.0410 (5) | |
H2 | 0.1809 | 0.2255 | 0.6316 | 0.049* | |
C3 | 0.19917 (19) | 0.3823 (3) | 0.70762 (12) | 0.0467 (6) | |
H3A | 0.1369 | 0.4284 | 0.6990 | 0.056* | |
H3B | 0.2369 | 0.4404 | 0.6866 | 0.056* | |
C4 | 0.25159 (18) | 0.3652 (3) | 0.78437 (12) | 0.0429 (5) | |
H4 | 0.2042 | 0.3622 | 0.8083 | 0.051* | |
C5 | 0.3250 (2) | 0.4850 (3) | 0.81550 (15) | 0.0553 (7) | |
H5A | 0.3315 | 0.5008 | 0.8632 | 0.066* | |
H5B | 0.3056 | 0.5758 | 0.7907 | 0.066* | |
C6 | 0.40350 (16) | 0.2381 (3) | 0.83063 (12) | 0.0395 (5) | |
H6 | 0.4396 | 0.1643 | 0.8149 | 0.047* | |
C7 | 0.28028 (17) | 0.1525 (2) | 0.72437 (11) | 0.0363 (5) | |
H7 | 0.3328 | 0.1671 | 0.7058 | 0.044* | |
C8 | 0.25517 (16) | −0.0092 (2) | 0.72572 (11) | 0.0367 (5) | |
H8 | 0.2853 | −0.0476 | 0.7722 | 0.044* | |
C9 | 0.42549 (17) | 0.2203 (3) | 0.90772 (12) | 0.0410 (5) | |
C10 | 0.5014 (2) | 0.2919 (4) | 0.95574 (15) | 0.0731 (10) | |
H10 | 0.5400 | 0.3546 | 0.9409 | 0.088* | |
C11 | 0.5207 (3) | 0.2717 (4) | 1.02547 (16) | 0.0811 (11) | |
H11 | 0.5710 | 0.3219 | 1.0570 | 0.097* | |
C12 | 0.4660 (2) | 0.1786 (3) | 1.04730 (13) | 0.0562 (7) | |
C13 | 0.3929 (2) | 0.1029 (4) | 1.00161 (14) | 0.0609 (7) | |
H13 | 0.3571 | 0.0365 | 1.0171 | 0.073* | |
C14 | 0.3721 (2) | 0.1254 (3) | 0.93180 (13) | 0.0527 (7) | |
H14 | 0.3211 | 0.0754 | 0.9008 | 0.063* | |
C15 | 0.11462 (17) | −0.0912 (3) | 0.82527 (12) | 0.0415 (5) | |
C16 | 0.0647 (2) | 0.0213 (3) | 0.84274 (15) | 0.0556 (7) | |
H16 | 0.0197 | 0.0753 | 0.8088 | 0.067* | |
C17 | 0.0823 (3) | 0.0527 (4) | 0.91136 (18) | 0.0692 (9) | |
H17 | 0.0499 | 0.1299 | 0.9232 | 0.083* | |
C18 | 0.1470 (3) | −0.0284 (4) | 0.96248 (16) | 0.0658 (8) | |
C19 | 0.1947 (2) | −0.1405 (3) | 0.94410 (15) | 0.0630 (8) | |
H19 | 0.2383 | −0.1959 | 0.9782 | 0.076* | |
C20 | 0.1799 (2) | −0.1734 (3) | 0.87601 (14) | 0.0506 (6) | |
H20 | 0.2133 | −0.2496 | 0.8645 | 0.061* | |
C21 | 0.1633 (4) | 0.0068 (5) | 1.0370 (2) | 0.1075 (15) | |
H21A | 0.2159 | −0.0505 | 1.0656 | 0.161* | |
H21B | 0.1060 | −0.0152 | 1.0475 | 0.161* | |
H21C | 0.1782 | 0.1086 | 1.0450 | 0.161* | |
C22 | 0.28483 (18) | −0.1044 (3) | 0.67417 (13) | 0.0445 (6) | |
H22A | 0.3545 | −0.1023 | 0.6869 | 0.053* | |
H22B | 0.2661 | −0.2044 | 0.6784 | 0.053* | |
C23 | 0.24224 (17) | −0.0594 (3) | 0.60049 (12) | 0.0432 (6) | |
C24 | 0.1489 (2) | −0.0971 (4) | 0.56192 (15) | 0.0618 (8) | |
H24 | 0.1122 | −0.1531 | 0.5815 | 0.074* | |
C25 | 0.1095 (2) | −0.0517 (5) | 0.49398 (17) | 0.0836 (12) | |
H25 | 0.0463 | −0.0763 | 0.4688 | 0.100* | |
C26 | 0.1624 (3) | 0.0282 (5) | 0.46399 (17) | 0.0868 (12) | |
H26 | 0.1358 | 0.0580 | 0.4186 | 0.104* | |
C27 | 0.2548 (3) | 0.0642 (4) | 0.50122 (16) | 0.0733 (9) | |
H27 | 0.2917 | 0.1180 | 0.4809 | 0.088* | |
C28 | 0.2944 (2) | 0.0213 (3) | 0.56895 (14) | 0.0550 (7) | |
H28 | 0.3574 | 0.0475 | 0.5937 | 0.066* | |
N1 | 0.14897 (14) | −0.0068 (2) | 0.70883 (9) | 0.0382 (4) | |
N2 | 0.30182 (13) | 0.2218 (2) | 0.79237 (9) | 0.0356 (4) | |
O1 | 0.13953 (15) | −0.26627 (19) | 0.73505 (10) | 0.0568 (5) | |
O2 | −0.00631 (13) | −0.1115 (2) | 0.70266 (10) | 0.0609 (5) | |
S1 | 0.09438 (4) | −0.12964 (6) | 0.73830 (3) | 0.04214 (16) | |
S2 | 0.43692 (5) | 0.42057 (8) | 0.80806 (4) | 0.0562 (2) | |
Br1 | 0.48802 (3) | 0.15400 (4) | 1.142767 (15) | 0.08422 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0374 (12) | 0.0426 (13) | 0.0468 (14) | −0.0008 (10) | 0.0033 (10) | 0.0028 (11) |
C2 | 0.0492 (13) | 0.0390 (12) | 0.0296 (11) | −0.0027 (10) | 0.0059 (10) | 0.0030 (9) |
C3 | 0.0526 (15) | 0.0395 (13) | 0.0411 (13) | −0.0001 (11) | 0.0062 (11) | 0.0022 (10) |
C4 | 0.0458 (14) | 0.0427 (13) | 0.0391 (13) | 0.0044 (10) | 0.0127 (11) | −0.0048 (10) |
C5 | 0.0628 (17) | 0.0423 (14) | 0.0516 (15) | −0.0010 (12) | 0.0069 (13) | −0.0082 (12) |
C6 | 0.0375 (12) | 0.0409 (12) | 0.0363 (12) | −0.0027 (9) | 0.0073 (9) | −0.0032 (9) |
C7 | 0.0402 (12) | 0.0391 (12) | 0.0295 (11) | −0.0023 (9) | 0.0114 (9) | −0.0038 (9) |
C8 | 0.0405 (12) | 0.0375 (12) | 0.0293 (10) | 0.0006 (9) | 0.0079 (9) | −0.0009 (9) |
C9 | 0.0405 (12) | 0.0391 (12) | 0.0371 (12) | 0.0017 (10) | 0.0046 (10) | −0.0016 (10) |
C10 | 0.074 (2) | 0.082 (2) | 0.0448 (16) | −0.0341 (18) | −0.0040 (14) | 0.0038 (15) |
C11 | 0.088 (2) | 0.084 (2) | 0.0440 (17) | −0.028 (2) | −0.0140 (16) | −0.0028 (16) |
C12 | 0.0737 (19) | 0.0542 (16) | 0.0305 (12) | 0.0173 (14) | 0.0038 (12) | −0.0017 (11) |
C13 | 0.0669 (18) | 0.0734 (19) | 0.0400 (14) | −0.0070 (15) | 0.0144 (13) | 0.0028 (13) |
C14 | 0.0542 (15) | 0.0629 (17) | 0.0351 (13) | −0.0135 (13) | 0.0069 (11) | −0.0062 (12) |
C15 | 0.0470 (13) | 0.0386 (12) | 0.0420 (13) | −0.0082 (10) | 0.0189 (11) | −0.0016 (10) |
C16 | 0.0619 (17) | 0.0505 (15) | 0.0611 (17) | 0.0056 (13) | 0.0292 (14) | 0.0051 (13) |
C17 | 0.093 (2) | 0.0591 (18) | 0.074 (2) | −0.0032 (17) | 0.053 (2) | −0.0127 (16) |
C18 | 0.084 (2) | 0.072 (2) | 0.0508 (17) | −0.0246 (17) | 0.0348 (16) | −0.0119 (15) |
C19 | 0.075 (2) | 0.0686 (19) | 0.0437 (15) | −0.0090 (16) | 0.0167 (14) | 0.0069 (14) |
C20 | 0.0596 (16) | 0.0471 (14) | 0.0454 (14) | 0.0017 (12) | 0.0177 (12) | 0.0026 (11) |
C21 | 0.148 (4) | 0.130 (4) | 0.059 (2) | −0.033 (3) | 0.053 (2) | −0.027 (2) |
C22 | 0.0442 (13) | 0.0425 (13) | 0.0461 (14) | 0.0060 (10) | 0.0141 (11) | −0.0056 (11) |
C23 | 0.0423 (13) | 0.0468 (14) | 0.0400 (12) | 0.0041 (10) | 0.0132 (10) | −0.0137 (10) |
C24 | 0.0487 (15) | 0.087 (2) | 0.0506 (16) | −0.0074 (15) | 0.0173 (13) | −0.0258 (15) |
C25 | 0.0554 (18) | 0.135 (3) | 0.0477 (18) | 0.020 (2) | −0.0001 (15) | −0.033 (2) |
C26 | 0.109 (3) | 0.105 (3) | 0.0399 (16) | 0.042 (2) | 0.0153 (19) | −0.0017 (18) |
C27 | 0.106 (3) | 0.071 (2) | 0.0481 (17) | 0.0014 (19) | 0.0318 (18) | −0.0008 (15) |
C28 | 0.0609 (17) | 0.0581 (16) | 0.0481 (15) | −0.0041 (13) | 0.0208 (13) | −0.0085 (13) |
N1 | 0.0419 (10) | 0.0375 (10) | 0.0340 (10) | −0.0005 (8) | 0.0112 (8) | −0.0013 (8) |
N2 | 0.0361 (10) | 0.0387 (10) | 0.0300 (9) | −0.0026 (8) | 0.0082 (8) | −0.0040 (7) |
O1 | 0.0792 (13) | 0.0361 (9) | 0.0584 (11) | −0.0072 (9) | 0.0275 (10) | −0.0088 (8) |
O2 | 0.0471 (10) | 0.0716 (13) | 0.0553 (12) | −0.0184 (9) | 0.0053 (9) | −0.0001 (10) |
S1 | 0.0472 (3) | 0.0381 (3) | 0.0393 (3) | −0.0098 (2) | 0.0121 (3) | −0.0045 (2) |
S2 | 0.0528 (4) | 0.0585 (4) | 0.0528 (4) | −0.0167 (3) | 0.0115 (3) | 0.0059 (3) |
Br1 | 0.1294 (4) | 0.0764 (3) | 0.03267 (17) | 0.0335 (2) | 0.00817 (17) | 0.00115 (13) |
C1—N1 | 1.473 (3) | C13—H13 | 0.93 |
C1—C2 | 1.520 (3) | C14—H14 | 0.93 |
C1—H1A | 0.97 | C15—C16 | 1.383 (4) |
C1—H1B | 0.97 | C15—C20 | 1.385 (4) |
C2—C3 | 1.512 (3) | C15—S1 | 1.758 (2) |
C2—C7 | 1.530 (3) | C16—C17 | 1.385 (4) |
C2—H2 | 0.98 | C16—H16 | 0.93 |
C3—C4 | 1.524 (3) | C17—C18 | 1.381 (5) |
C3—H3A | 0.97 | C17—H17 | 0.93 |
C3—H3B | 0.97 | C18—C19 | 1.369 (5) |
C4—N2 | 1.490 (3) | C18—C21 | 1.513 (4) |
C4—C5 | 1.525 (4) | C19—C20 | 1.384 (4) |
C4—H4 | 0.98 | C19—H19 | 0.93 |
C5—S2 | 1.804 (3) | C20—H20 | 0.93 |
C5—H5A | 0.97 | C21—H21A | 0.96 |
C5—H5B | 0.97 | C21—H21B | 0.96 |
C6—N2 | 1.449 (3) | C21—H21C | 0.96 |
C6—C9 | 1.526 (3) | C22—C23 | 1.500 (4) |
C6—S2 | 1.847 (2) | C22—H22A | 0.97 |
C6—H6 | 0.98 | C22—H22B | 0.97 |
C7—N2 | 1.478 (3) | C23—C28 | 1.376 (4) |
C7—C8 | 1.530 (3) | C23—C24 | 1.383 (4) |
C7—H7 | 0.98 | C24—C25 | 1.393 (5) |
C8—N1 | 1.484 (3) | C24—H24 | 0.93 |
C8—C22 | 1.549 (3) | C25—C26 | 1.361 (6) |
C8—H8 | 0.98 | C25—H25 | 0.93 |
C9—C14 | 1.372 (4) | C26—C27 | 1.362 (5) |
C9—C10 | 1.388 (4) | C26—H26 | 0.93 |
C10—C11 | 1.386 (4) | C27—C28 | 1.383 (4) |
C10—H10 | 0.93 | C27—H27 | 0.93 |
C11—C12 | 1.350 (5) | C28—H28 | 0.93 |
C11—H11 | 0.93 | N1—S1 | 1.616 (2) |
C12—C13 | 1.362 (4) | O1—S1 | 1.430 (2) |
C12—Br1 | 1.905 (3) | O2—S1 | 1.428 (2) |
C13—C14 | 1.388 (4) | ||
N1—C1—C2 | 103.56 (19) | C9—C14—H14 | 119.4 |
N1—C1—H1A | 111.0 | C13—C14—H14 | 119.4 |
C2—C1—H1A | 111.0 | C16—C15—C20 | 120.2 (2) |
N1—C1—H1B | 111.0 | C16—C15—S1 | 119.5 (2) |
C2—C1—H1B | 111.0 | C20—C15—S1 | 120.3 (2) |
H1A—C1—H1B | 109.0 | C15—C16—C17 | 119.2 (3) |
C3—C2—C1 | 114.5 (2) | C15—C16—H16 | 120.4 |
C3—C2—C7 | 103.57 (18) | C17—C16—H16 | 120.4 |
C1—C2—C7 | 103.71 (18) | C18—C17—C16 | 121.2 (3) |
C3—C2—H2 | 111.5 | C18—C17—H17 | 119.4 |
C1—C2—H2 | 111.5 | C16—C17—H17 | 119.4 |
C7—C2—H2 | 111.5 | C19—C18—C17 | 118.6 (3) |
C2—C3—C4 | 104.28 (19) | C19—C18—C21 | 121.4 (4) |
C2—C3—H3A | 110.9 | C17—C18—C21 | 120.0 (4) |
C4—C3—H3A | 110.9 | C18—C19—C20 | 121.6 (3) |
C2—C3—H3B | 110.9 | C18—C19—H19 | 119.2 |
C4—C3—H3B | 110.9 | C20—C19—H19 | 119.2 |
H3A—C3—H3B | 108.9 | C19—C20—C15 | 119.1 (3) |
N2—C4—C3 | 105.49 (18) | C19—C20—H20 | 120.4 |
N2—C4—C5 | 109.46 (19) | C15—C20—H20 | 120.4 |
C3—C4—C5 | 114.0 (2) | C18—C21—H21A | 109.5 |
N2—C4—H4 | 109.3 | C18—C21—H21B | 109.5 |
C3—C4—H4 | 109.3 | H21A—C21—H21B | 109.5 |
C5—C4—H4 | 109.3 | C18—C21—H21C | 109.5 |
C4—C5—S2 | 105.48 (17) | H21A—C21—H21C | 109.5 |
C4—C5—H5A | 110.6 | H21B—C21—H21C | 109.5 |
S2—C5—H5A | 110.6 | C23—C22—C8 | 115.22 (19) |
C4—C5—H5B | 110.6 | C23—C22—H22A | 108.5 |
S2—C5—H5B | 110.6 | C8—C22—H22A | 108.5 |
H5A—C5—H5B | 108.8 | C23—C22—H22B | 108.5 |
N2—C6—C9 | 112.35 (19) | C8—C22—H22B | 108.5 |
N2—C6—S2 | 105.63 (15) | H22A—C22—H22B | 107.5 |
C9—C6—S2 | 112.29 (16) | C28—C23—C24 | 117.7 (3) |
N2—C6—H6 | 108.8 | C28—C23—C22 | 121.3 (2) |
C9—C6—H6 | 108.8 | C24—C23—C22 | 121.1 (2) |
S2—C6—H6 | 108.8 | C23—C24—C25 | 120.5 (3) |
N2—C7—C2 | 103.76 (17) | C23—C24—H24 | 119.8 |
N2—C7—C8 | 112.06 (18) | C25—C24—H24 | 119.8 |
C2—C7—C8 | 106.06 (18) | C26—C25—C24 | 120.8 (3) |
N2—C7—H7 | 111.5 | C26—C25—H25 | 119.6 |
C2—C7—H7 | 111.5 | C24—C25—H25 | 119.6 |
C8—C7—H7 | 111.5 | C25—C26—C27 | 119.2 (3) |
N1—C8—C7 | 102.89 (17) | C25—C26—H26 | 120.4 |
N1—C8—C22 | 111.27 (18) | C27—C26—H26 | 120.4 |
C7—C8—C22 | 114.08 (19) | C26—C27—C28 | 120.5 (3) |
N1—C8—H8 | 109.5 | C26—C27—H27 | 119.7 |
C7—C8—H8 | 109.5 | C28—C27—H27 | 119.7 |
C22—C8—H8 | 109.5 | C23—C28—C27 | 121.3 (3) |
C14—C9—C10 | 117.5 (2) | C23—C28—H28 | 119.3 |
C14—C9—C6 | 119.9 (2) | C27—C28—H28 | 119.3 |
C10—C9—C6 | 122.5 (2) | C1—N1—C8 | 112.7 (2) |
C11—C10—C9 | 121.2 (3) | C1—N1—S1 | 119.9 (2) |
C11—C10—H10 | 119.4 | C8—N1—S1 | 121.2 (2) |
C9—C10—H10 | 119.4 | C6—N2—C7 | 114.8 (2) |
C12—C11—C10 | 119.6 (3) | C6—N2—C4 | 110.7 (2) |
C12—C11—H11 | 120.2 | C7—N2—C4 | 109.4 (2) |
C10—C11—H11 | 120.2 | O2—S1—O1 | 119.8 (1) |
C11—C12—C13 | 120.8 (3) | O2—S1—N1 | 106.6 (1) |
C11—C12—Br1 | 120.4 (2) | O1—S1—N1 | 107.2 (1) |
C13—C12—Br1 | 118.8 (2) | O2—S1—C15 | 107.3 (1) |
C12—C13—C14 | 119.7 (3) | O1—S1—C15 | 107.5 (1) |
C12—C13—H13 | 120.1 | N1—S1—C15 | 108.1 (1) |
C14—C13—H13 | 120.1 | C5—S2—C6 | 87.0 (1) |
C9—C14—C13 | 121.1 (2) | ||
N1—C1—C2—C3 | −142.7 (2) | C8—C22—C23—C24 | −79.9 (3) |
N1—C1—C2—C7 | −30.6 (2) | C28—C23—C24—C25 | −1.2 (4) |
C1—C2—C3—C4 | 76.6 (3) | C22—C23—C24—C25 | 178.5 (3) |
C7—C2—C3—C4 | −35.6 (2) | C23—C24—C25—C26 | 1.1 (5) |
C2—C3—C4—N2 | 22.9 (3) | C24—C25—C26—C27 | −0.2 (6) |
C2—C3—C4—C5 | 143.0 (2) | C25—C26—C27—C28 | −0.6 (5) |
N2—C4—C5—S2 | 28.1 (2) | C24—C23—C28—C27 | 0.4 (4) |
C3—C4—C5—S2 | −89.8 (2) | C22—C23—C28—C27 | −179.3 (3) |
C3—C2—C7—N2 | 34.8 (2) | C26—C27—C28—C23 | 0.5 (5) |
C1—C2—C7—N2 | −85.0 (2) | C2—C1—N1—C8 | 17.9 (2) |
C3—C2—C7—C8 | 153.05 (19) | C2—C1—N1—S1 | 170.49 (15) |
C1—C2—C7—C8 | 33.2 (2) | C7—C8—N1—C1 | 2.5 (2) |
N2—C7—C8—N1 | 90.6 (2) | C22—C8—N1—C1 | −120.1 (2) |
C2—C7—C8—N1 | −22.0 (2) | C7—C8—N1—S1 | −149.70 (15) |
N2—C7—C8—C22 | −148.78 (19) | C22—C8—N1—S1 | 87.7 (2) |
C2—C7—C8—C22 | 98.7 (2) | C9—C6—N2—C7 | −145.5 (2) |
N2—C6—C9—C14 | 33.3 (3) | S2—C6—N2—C7 | 91.76 (19) |
S2—C6—C9—C14 | 152.2 (2) | C9—C6—N2—C4 | 90.0 (2) |
N2—C6—C9—C10 | −149.8 (3) | S2—C6—N2—C4 | −32.7 (2) |
S2—C6—C9—C10 | −30.9 (3) | C2—C7—N2—C6 | −146.11 (19) |
C14—C9—C10—C11 | −1.9 (5) | C8—C7—N2—C6 | 99.9 (2) |
C6—C9—C10—C11 | −178.9 (3) | C2—C7—N2—C4 | −21.0 (2) |
C9—C10—C11—C12 | 1.3 (6) | C8—C7—N2—C4 | −134.98 (19) |
C10—C11—C12—C13 | 0.9 (5) | C3—C4—N2—C6 | 126.5 (2) |
C10—C11—C12—Br1 | −177.8 (3) | C5—C4—N2—C6 | 3.4 (3) |
C11—C12—C13—C14 | −2.3 (5) | C3—C4—N2—C7 | −1.0 (2) |
Br1—C12—C13—C14 | 176.4 (2) | C5—C4—N2—C7 | −124.0 (2) |
C10—C9—C14—C13 | 0.5 (4) | C1—N1—S1—O2 | 40.2 (2) |
C6—C9—C14—C13 | 177.5 (3) | C8—N1—S1—O2 | −169.51 (17) |
C12—C13—C14—C9 | 1.6 (5) | C1—N1—S1—O1 | 169.61 (18) |
C20—C15—C16—C17 | 1.4 (4) | C8—N1—S1—O1 | −40.14 (19) |
S1—C15—C16—C17 | −178.8 (2) | C1—N1—S1—C15 | −74.8 (2) |
C15—C16—C17—C18 | −1.6 (5) | C8—N1—S1—C15 | 75.44 (19) |
C16—C17—C18—C19 | 0.7 (5) | C16—C15—S1—O2 | −38.5 (2) |
C16—C17—C18—C21 | −178.8 (3) | C20—C15—S1—O2 | 141.2 (2) |
C17—C18—C19—C20 | 0.3 (5) | C16—C15—S1—O1 | −168.6 (2) |
C21—C18—C19—C20 | 179.8 (3) | C20—C15—S1—O1 | 11.2 (2) |
C18—C19—C20—C15 | −0.4 (4) | C16—C15—S1—N1 | 76.0 (2) |
C16—C15—C20—C19 | −0.5 (4) | C20—C15—S1—N1 | −104.2 (2) |
S1—C15—C20—C19 | 179.8 (2) | C4—C5—S2—C6 | −39.49 (18) |
N1—C8—C22—C23 | 57.8 (3) | N2—C6—S2—C5 | 42.26 (16) |
C7—C8—C22—C23 | −58.0 (3) | C9—C6—S2—C5 | −80.52 (18) |
C8—C22—C23—C28 | 99.8 (3) |