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Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229619009185/yo3065sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S2053229619009185/yo3065Isup2.hkl |
![]() | Portable Document Format (PDF) file https://doi.org/10.1107/S2053229619009185/yo3065sup3.pdf |
CCDC reference: 1572644
Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
C20H23F3N4O3S | F(000) = 952 |
Mr = 456.48 | Dx = 1.445 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.051 (7) Å | Cell parameters from 4036 reflections |
b = 5.295 (2) Å | θ = 2.7–27.7° |
c = 26.548 (11) Å | µ = 0.21 mm−1 |
β = 97.372 (7)° | T = 205 K |
V = 2098.3 (15) Å3 | Block, colourless |
Z = 4 | 0.16 × 0.15 × 0.12 mm |
Bruker D8 Venture diffractometer | 3412 reflections with I > 2σ(I) |
phi and ω scans | Rint = 0.025 |
Absorption correction: multi-scan (SADABS; Bruker, 2014/3) | θmax = 27.7°, θmin = 1.9° |
Tmin = 0.641, Tmax = 0.746 | h = −19→18 |
11854 measured reflections | k = −6→6 |
4794 independent reflections | l = −26→34 |
Refinement on F2 | Primary atom site location: dual |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.122 | w = 1/[σ2(Fo2) + (0.0422P)2 + 1.0593P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
4794 reflections | Δρmax = 0.28 e Å−3 |
326 parameters | Δρmin = −0.21 e Å−3 |
36 restraints |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Single-crystal X-ray diffraction measurements were carried out on a Bruker SMART APEXII CCD diffractometer at 205.0 K using graphite-monochromated Mo Kα radiation (λ = 0.71070 Å). Absorption correction was performed with Multi-scan BRUKER SADABS. All structures were solved by direct methods and refined by full-matrix least squares on F2 using the OLEX 2-1.2 computer program package. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
S1 | 0.52703 (3) | 0.65072 (11) | 0.42522 (2) | 0.04694 (16) | |
F1 | 0.8552 (9) | −0.1746 (17) | 0.4930 (6) | 0.108 (3) | 0.54 (2) |
F1A | 0.8725 (9) | −0.143 (3) | 0.4794 (5) | 0.111 (4) | 0.46 (2) |
F2 | 0.9241 (6) | 0.170 (3) | 0.4874 (6) | 0.128 (4) | 0.54 (2) |
F2A | 0.9244 (7) | 0.184 (2) | 0.5097 (9) | 0.125 (5) | 0.46 (2) |
F3 | 0.8780 (7) | 0.076 (3) | 0.5547 (4) | 0.102 (3) | 0.54 (2) |
F3A | 0.8502 (11) | −0.052 (4) | 0.5517 (5) | 0.129 (5) | 0.46 (2) |
O1 | 0.63947 (12) | 0.0187 (4) | 0.34831 (6) | 0.0694 (5) | |
O2 | 0.5728 (11) | 0.832 (3) | 0.5164 (5) | 0.070 (4) | 0.5 |
O3 | 0.6875 (10) | 0.755 (3) | 0.5709 (6) | 0.081 (4) | 0.5 |
N1 | 0.54185 (11) | 0.3384 (4) | 0.34317 (6) | 0.0487 (4) | |
N2 | 0.63712 (12) | 0.7050 (4) | 0.53079 (7) | 0.0526 (5) | |
N3 | 0.43493 (11) | 0.6421 (4) | 0.33536 (6) | 0.0515 (5) | |
N4 | 0.26569 (10) | 0.7797 (3) | 0.28300 (6) | 0.0434 (4) | |
C1 | 0.50279 (12) | 0.5254 (4) | 0.36293 (7) | 0.0425 (5) | |
C2 | 0.61018 (13) | 0.2030 (5) | 0.36797 (7) | 0.0464 (5) | |
C3 | 0.65155 (12) | 0.2764 (4) | 0.42019 (7) | 0.0413 (5) | |
C4 | 0.61939 (12) | 0.4688 (4) | 0.44857 (7) | 0.0372 (4) | |
C5 | 0.66502 (12) | 0.5100 (4) | 0.49754 (7) | 0.0410 (5) | |
C6 | 0.73970 (13) | 0.3740 (4) | 0.51622 (8) | 0.0468 (5) | |
H6 | 0.769070 | 0.407636 | 0.548954 | 0.056* | |
C7 | 0.77130 (13) | 0.1896 (4) | 0.48713 (8) | 0.0479 (5) | |
C8 | 0.85604 (17) | 0.0546 (6) | 0.50615 (10) | 0.0662 (7) | |
C9 | 0.72686 (13) | 0.1392 (5) | 0.43980 (8) | 0.0486 (5) | |
H9 | 0.747755 | 0.009301 | 0.420233 | 0.058* | |
C10 | 0.41082 (14) | 0.5820 (6) | 0.28127 (8) | 0.0603 (7) | |
H10A | 0.439959 | 0.424089 | 0.273247 | 0.072* | |
H10B | 0.431976 | 0.716647 | 0.260462 | 0.072* | |
C11 | 0.31140 (14) | 0.5553 (5) | 0.26915 (7) | 0.0493 (5) | |
H11A | 0.296009 | 0.523696 | 0.232706 | 0.059* | |
H11B | 0.291271 | 0.409934 | 0.287546 | 0.059* | |
C12 | 0.28611 (15) | 0.8181 (5) | 0.33727 (7) | 0.0543 (6) | |
H12A | 0.266122 | 0.671138 | 0.355248 | 0.065* | |
H12B | 0.253750 | 0.966621 | 0.347326 | 0.065* | |
C13 | 0.38519 (16) | 0.8555 (5) | 0.35200 (9) | 0.0615 (7) | |
H13A | 0.404235 | 1.010959 | 0.336436 | 0.074* | |
H13B | 0.398081 | 0.873235 | 0.388956 | 0.074* | |
C14 | 0.16929 (13) | 0.7631 (5) | 0.26748 (8) | 0.0508 (5) | |
H14A | 0.139390 | 0.893787 | 0.285327 | 0.061* | |
H14B | 0.148037 | 0.598650 | 0.277928 | 0.061* | |
C15 | 0.14244 (13) | 0.7943 (4) | 0.21079 (7) | 0.0431 (5) | |
H15 | 0.174017 | 0.663337 | 0.193265 | 0.052* | |
C16 | 0.16959 (17) | 1.0481 (5) | 0.19249 (9) | 0.0625 (6) | |
H16A | 0.235041 | 1.062146 | 0.198156 | 0.075* | |
H16B | 0.144881 | 1.180598 | 0.212410 | 0.075* | |
C17 | 0.1376 (2) | 1.0897 (6) | 0.13692 (10) | 0.0831 (9) | |
H17A | 0.152016 | 1.262774 | 0.127726 | 0.100* | |
H17B | 0.169625 | 0.974292 | 0.116704 | 0.100* | |
C18 | 0.0386 (2) | 1.0477 (6) | 0.12409 (11) | 0.0823 (9) | |
H18A | 0.006208 | 1.179663 | 0.140110 | 0.099* | |
H18B | 0.022299 | 1.060636 | 0.087238 | 0.099* | |
C19 | 0.01126 (18) | 0.7948 (6) | 0.14168 (10) | 0.0745 (8) | |
H19A | 0.036229 | 0.662908 | 0.121730 | 0.089* | |
H19B | −0.054178 | 0.780856 | 0.135811 | 0.089* | |
C20 | 0.04285 (15) | 0.7530 (6) | 0.19717 (9) | 0.0645 (7) | |
H20A | 0.028111 | 0.580029 | 0.206253 | 0.077* | |
H20B | 0.010587 | 0.868432 | 0.217269 | 0.077* | |
O3A | 0.6660 (9) | 0.690 (3) | 0.5751 (5) | 0.063 (2) | 0.5 |
O2A | 0.5785 (13) | 0.850 (4) | 0.5140 (6) | 0.080 (4) | 0.5 |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0422 (3) | 0.0577 (4) | 0.0374 (3) | 0.0079 (2) | −0.00828 (19) | −0.0052 (2) |
F1 | 0.092 (5) | 0.053 (3) | 0.168 (8) | 0.019 (3) | −0.029 (5) | −0.001 (3) |
F1A | 0.079 (5) | 0.132 (8) | 0.107 (5) | 0.066 (5) | −0.043 (4) | −0.058 (6) |
F2 | 0.040 (3) | 0.164 (8) | 0.183 (8) | 0.031 (3) | 0.020 (4) | 0.080 (6) |
F2A | 0.048 (4) | 0.091 (5) | 0.221 (12) | 0.001 (3) | −0.047 (6) | −0.023 (7) |
F3 | 0.090 (4) | 0.129 (7) | 0.074 (3) | 0.048 (4) | −0.042 (3) | −0.010 (4) |
F3A | 0.124 (7) | 0.174 (11) | 0.085 (5) | 0.080 (7) | −0.001 (5) | 0.042 (6) |
O1 | 0.0746 (11) | 0.0853 (13) | 0.0458 (9) | 0.0258 (10) | −0.0022 (8) | −0.0171 (9) |
O2 | 0.072 (6) | 0.100 (10) | 0.035 (4) | 0.050 (6) | −0.008 (4) | −0.016 (4) |
O3 | 0.073 (7) | 0.091 (9) | 0.070 (6) | 0.017 (5) | −0.031 (5) | −0.043 (5) |
N1 | 0.0419 (9) | 0.0666 (13) | 0.0354 (8) | 0.0050 (9) | −0.0031 (7) | −0.0064 (9) |
N2 | 0.0508 (10) | 0.0619 (13) | 0.0419 (10) | 0.0087 (10) | −0.0067 (8) | −0.0093 (9) |
N3 | 0.0428 (9) | 0.0688 (13) | 0.0390 (9) | 0.0082 (9) | −0.0094 (7) | −0.0053 (9) |
N4 | 0.0404 (9) | 0.0533 (11) | 0.0337 (8) | 0.0026 (8) | −0.0065 (6) | −0.0019 (8) |
C1 | 0.0327 (9) | 0.0573 (14) | 0.0354 (9) | −0.0037 (9) | −0.0033 (7) | 0.0010 (9) |
C2 | 0.0411 (10) | 0.0625 (15) | 0.0353 (10) | 0.0037 (10) | 0.0037 (8) | −0.0052 (10) |
C3 | 0.0338 (9) | 0.0532 (13) | 0.0362 (10) | −0.0008 (9) | 0.0014 (7) | 0.0007 (9) |
C4 | 0.0305 (9) | 0.0463 (12) | 0.0337 (9) | −0.0029 (8) | −0.0002 (7) | 0.0025 (8) |
C5 | 0.0369 (10) | 0.0489 (13) | 0.0357 (10) | −0.0004 (9) | −0.0018 (7) | −0.0031 (9) |
C6 | 0.0384 (10) | 0.0585 (14) | 0.0405 (10) | −0.0007 (10) | −0.0066 (8) | −0.0007 (10) |
C7 | 0.0365 (10) | 0.0575 (14) | 0.0474 (11) | 0.0065 (10) | −0.0032 (8) | 0.0002 (11) |
C8 | 0.0518 (14) | 0.0741 (19) | 0.0668 (16) | 0.0172 (13) | −0.0144 (12) | −0.0065 (14) |
C9 | 0.0382 (10) | 0.0606 (15) | 0.0463 (11) | 0.0061 (10) | 0.0029 (8) | −0.0055 (11) |
C10 | 0.0479 (12) | 0.098 (2) | 0.0328 (10) | 0.0152 (13) | −0.0042 (9) | −0.0019 (12) |
C11 | 0.0487 (11) | 0.0646 (15) | 0.0319 (10) | 0.0043 (11) | −0.0056 (8) | −0.0067 (10) |
C12 | 0.0557 (12) | 0.0663 (16) | 0.0369 (10) | 0.0179 (11) | −0.0095 (9) | −0.0117 (10) |
C13 | 0.0616 (14) | 0.0593 (15) | 0.0552 (13) | 0.0123 (12) | −0.0248 (11) | −0.0148 (12) |
C14 | 0.0394 (10) | 0.0706 (16) | 0.0403 (11) | 0.0025 (10) | −0.0025 (8) | 0.0004 (10) |
C15 | 0.0428 (10) | 0.0447 (12) | 0.0386 (10) | 0.0037 (9) | −0.0070 (8) | −0.0023 (9) |
C16 | 0.0654 (15) | 0.0550 (15) | 0.0618 (14) | −0.0078 (12) | −0.0122 (11) | 0.0056 (12) |
C17 | 0.098 (2) | 0.081 (2) | 0.0654 (17) | −0.0008 (17) | −0.0073 (15) | 0.0278 (16) |
C18 | 0.100 (2) | 0.0721 (19) | 0.0639 (16) | 0.0223 (17) | −0.0313 (15) | 0.0081 (15) |
C19 | 0.0699 (16) | 0.078 (2) | 0.0659 (16) | 0.0025 (14) | −0.0305 (13) | −0.0043 (14) |
C20 | 0.0483 (12) | 0.0796 (18) | 0.0602 (14) | −0.0067 (13) | −0.0136 (10) | 0.0029 (13) |
O3A | 0.062 (5) | 0.082 (7) | 0.039 (2) | 0.011 (4) | −0.018 (3) | −0.016 (3) |
O2A | 0.090 (8) | 0.060 (6) | 0.080 (8) | 0.026 (5) | −0.027 (6) | −0.020 (5) |
S1—C1 | 1.776 (2) | C9—H9 | 0.9400 |
S1—C4 | 1.739 (2) | C10—H10A | 0.9800 |
F1—C8 | 1.262 (10) | C10—H10B | 0.9800 |
F1A—C8 | 1.305 (11) | C10—C11 | 1.496 (3) |
F2—C8 | 1.342 (9) | C11—H11A | 0.9800 |
F2A—C8 | 1.229 (11) | C11—H11B | 0.9800 |
F3—C8 | 1.293 (9) | C12—H12A | 0.9800 |
F3A—C8 | 1.347 (10) | C12—H12B | 0.9800 |
O1—C2 | 1.216 (3) | C12—C13 | 1.506 (3) |
O2—N2 | 1.200 (16) | C13—H13A | 0.9800 |
O3—N2 | 1.253 (14) | C13—H13B | 0.9800 |
N1—C1 | 1.296 (3) | C14—H14A | 0.9800 |
N1—C2 | 1.353 (3) | C14—H14B | 0.9800 |
N2—C5 | 1.455 (3) | C14—C15 | 1.516 (3) |
N2—O3A | 1.203 (14) | C15—H15 | 0.9900 |
N2—O2A | 1.211 (18) | C15—C16 | 1.504 (3) |
N3—C1 | 1.330 (2) | C15—C20 | 1.512 (3) |
N3—C10 | 1.470 (3) | C16—H16A | 0.9800 |
N3—C13 | 1.455 (3) | C16—H16B | 0.9800 |
N4—C11 | 1.444 (3) | C16—C17 | 1.508 (3) |
N4—C12 | 1.449 (2) | C17—H17A | 0.9800 |
N4—C14 | 1.459 (2) | C17—H17B | 0.9800 |
C2—C3 | 1.496 (3) | C17—C18 | 1.501 (4) |
C3—C4 | 1.390 (3) | C18—H18A | 0.9800 |
C3—C9 | 1.390 (3) | C18—H18B | 0.9800 |
C4—C5 | 1.407 (3) | C18—C19 | 1.494 (4) |
C5—C6 | 1.373 (3) | C19—H19A | 0.9800 |
C6—H6 | 0.9400 | C19—H19B | 0.9800 |
C6—C7 | 1.368 (3) | C19—C20 | 1.505 (3) |
C7—C8 | 1.492 (3) | C20—H20A | 0.9800 |
C7—C9 | 1.372 (3) | C20—H20B | 0.9800 |
C4—S1—C1 | 100.61 (10) | N4—C11—H11B | 109.4 |
C1—N1—C2 | 124.30 (17) | C10—C11—H11A | 109.4 |
O2—N2—O3 | 121.8 (11) | C10—C11—H11B | 109.4 |
O2—N2—C5 | 119.3 (6) | H11A—C11—H11B | 108.0 |
O3—N2—C5 | 118.3 (9) | N4—C12—H12A | 109.5 |
O3A—N2—C5 | 116.8 (9) | N4—C12—H12B | 109.5 |
O3A—N2—O2A | 123.7 (11) | N4—C12—C13 | 110.69 (18) |
O2A—N2—C5 | 118.8 (7) | H12A—C12—H12B | 108.1 |
C1—N3—C10 | 120.85 (19) | C13—C12—H12A | 109.5 |
C1—N3—C13 | 125.62 (17) | C13—C12—H12B | 109.5 |
C13—N3—C10 | 113.11 (17) | N3—C13—C12 | 110.48 (19) |
C11—N4—C12 | 108.74 (16) | N3—C13—H13A | 109.6 |
C11—N4—C14 | 111.55 (17) | N3—C13—H13B | 109.6 |
C12—N4—C14 | 111.45 (16) | C12—C13—H13A | 109.6 |
N1—C1—S1 | 127.78 (15) | C12—C13—H13B | 109.6 |
N1—C1—N3 | 119.23 (18) | H13A—C13—H13B | 108.1 |
N3—C1—S1 | 112.98 (16) | N4—C14—H14A | 108.8 |
O1—C2—N1 | 120.73 (19) | N4—C14—H14B | 108.8 |
O1—C2—C3 | 118.38 (19) | N4—C14—C15 | 113.72 (17) |
N1—C2—C3 | 120.89 (19) | H14A—C14—H14B | 107.7 |
C4—C3—C2 | 124.04 (17) | C15—C14—H14A | 108.8 |
C9—C3—C2 | 115.71 (19) | C15—C14—H14B | 108.8 |
C9—C3—C4 | 120.25 (18) | C14—C15—H15 | 107.9 |
C3—C4—S1 | 122.06 (14) | C16—C15—C14 | 111.66 (18) |
C3—C4—C5 | 116.85 (17) | C16—C15—H15 | 107.9 |
C5—C4—S1 | 121.09 (16) | C16—C15—C20 | 110.74 (19) |
C4—C5—N2 | 121.74 (18) | C20—C15—C14 | 110.58 (18) |
C6—C5—N2 | 116.08 (17) | C20—C15—H15 | 107.9 |
C6—C5—C4 | 122.16 (19) | C15—C16—H16A | 109.1 |
C5—C6—H6 | 120.1 | C15—C16—H16B | 109.1 |
C7—C6—C5 | 119.89 (18) | C15—C16—C17 | 112.4 (2) |
C7—C6—H6 | 120.1 | H16A—C16—H16B | 107.9 |
C6—C7—C8 | 119.7 (2) | C17—C16—H16A | 109.1 |
C6—C7—C9 | 119.47 (19) | C17—C16—H16B | 109.1 |
C9—C7—C8 | 120.8 (2) | C16—C17—H17A | 109.1 |
F1—C8—F2 | 108.5 (8) | C16—C17—H17B | 109.1 |
F1—C8—F3 | 110.5 (7) | H17A—C17—H17B | 107.8 |
F1—C8—C7 | 112.9 (6) | C18—C17—C16 | 112.6 (2) |
F1A—C8—F3A | 101.1 (8) | C18—C17—H17A | 109.1 |
F1A—C8—C7 | 114.4 (5) | C18—C17—H17B | 109.1 |
F2—C8—C7 | 108.4 (5) | C17—C18—H18A | 109.3 |
F2A—C8—F1A | 105.8 (9) | C17—C18—H18B | 109.3 |
F2A—C8—F3A | 108.2 (7) | H18A—C18—H18B | 108.0 |
F2A—C8—C7 | 115.5 (7) | C19—C18—C17 | 111.5 (2) |
F3—C8—F2 | 102.6 (5) | C19—C18—H18A | 109.3 |
F3—C8—C7 | 113.2 (4) | C19—C18—H18B | 109.3 |
F3A—C8—C7 | 110.6 (5) | C18—C19—H19A | 109.2 |
C3—C9—H9 | 119.3 | C18—C19—H19B | 109.2 |
C7—C9—C3 | 121.3 (2) | C18—C19—C20 | 111.9 (2) |
C7—C9—H9 | 119.3 | H19A—C19—H19B | 107.9 |
N3—C10—H10A | 109.6 | C20—C19—H19A | 109.2 |
N3—C10—H10B | 109.6 | C20—C19—H19B | 109.2 |
N3—C10—C11 | 110.19 (17) | C15—C20—H20A | 109.0 |
H10A—C10—H10B | 108.1 | C15—C20—H20B | 109.0 |
C11—C10—H10A | 109.6 | C19—C20—C15 | 113.1 (2) |
C11—C10—H10B | 109.6 | C19—C20—H20A | 109.0 |
N4—C11—C10 | 111.31 (19) | C19—C20—H20B | 109.0 |
N4—C11—H11A | 109.4 | H20A—C20—H20B | 107.8 |
S1—C4—C5—N2 | 0.2 (3) | C6—C7—C8—F2A | −67.1 (12) |
S1—C4—C5—C6 | −177.98 (16) | C6—C7—C8—F3 | 18.7 (9) |
O1—C2—C3—C4 | −174.1 (2) | C6—C7—C8—F3A | 56.3 (13) |
O1—C2—C3—C9 | 6.2 (3) | C6—C7—C9—C3 | 1.7 (3) |
O2—N2—C5—C4 | 1.0 (11) | C8—C7—C9—C3 | −175.3 (2) |
O2—N2—C5—C6 | 179.3 (11) | C9—C3—C4—S1 | 178.49 (16) |
O3—N2—C5—C4 | −170.4 (7) | C9—C3—C4—C5 | −1.7 (3) |
O3—N2—C5—C6 | 7.9 (8) | C9—C7—C8—F1 | −37.8 (9) |
N1—C2—C3—C4 | 5.9 (3) | C9—C7—C8—F1A | −13.4 (11) |
N1—C2—C3—C9 | −173.8 (2) | C9—C7—C8—F2 | 82.5 (9) |
N2—C5—C6—C7 | −179.0 (2) | C9—C7—C8—F2A | 109.9 (12) |
N3—C10—C11—N4 | 56.2 (3) | C9—C7—C8—F3 | −164.3 (8) |
N4—C12—C13—N3 | −56.6 (3) | C9—C7—C8—F3A | −126.7 (13) |
N4—C14—C15—C16 | −61.0 (3) | C10—N3—C1—S1 | 173.83 (17) |
N4—C14—C15—C20 | 175.2 (2) | C10—N3—C1—N1 | −7.3 (3) |
C1—S1—C4—C3 | −2.88 (19) | C10—N3—C13—C12 | 51.9 (3) |
C1—S1—C4—C5 | 177.31 (17) | C11—N4—C12—C13 | 61.2 (2) |
C1—N1—C2—O1 | 174.7 (2) | C11—N4—C14—C15 | −73.9 (2) |
C1—N1—C2—C3 | −5.3 (3) | C12—N4—C11—C10 | −61.4 (2) |
C1—N3—C10—C11 | 135.4 (2) | C12—N4—C14—C15 | 164.3 (2) |
C1—N3—C13—C12 | −135.5 (2) | C13—N3—C1—S1 | 1.8 (3) |
C2—N1—C1—S1 | 0.1 (3) | C13—N3—C1—N1 | −179.3 (2) |
C2—N1—C1—N3 | −178.6 (2) | C13—N3—C10—C11 | −51.6 (3) |
C2—C3—C4—S1 | −1.2 (3) | C14—N4—C11—C10 | 175.31 (17) |
C2—C3—C4—C5 | 178.66 (19) | C14—N4—C12—C13 | −175.5 (2) |
C2—C3—C9—C7 | 179.5 (2) | C14—C15—C16—C17 | −175.9 (2) |
C3—C4—C5—N2 | −179.62 (18) | C14—C15—C20—C19 | 177.0 (2) |
C3—C4—C5—C6 | 2.2 (3) | C15—C16—C17—C18 | 53.5 (3) |
C4—S1—C1—N1 | 3.8 (2) | C16—C15—C20—C19 | 52.7 (3) |
C4—S1—C1—N3 | −177.46 (16) | C16—C17—C18—C19 | −53.5 (4) |
C4—C3—C9—C7 | −0.2 (3) | C17—C18—C19—C20 | 53.2 (3) |
C4—C5—C6—C7 | −0.8 (3) | C18—C19—C20—C15 | −53.7 (3) |
C5—C6—C7—C8 | 175.8 (2) | C20—C15—C16—C17 | −52.2 (3) |
C5—C6—C7—C9 | −1.2 (3) | O3A—N2—C5—C4 | 163.6 (6) |
C6—C7—C8—F1 | 145.3 (9) | O3A—N2—C5—C6 | −18.1 (7) |
C6—C7—C8—F1A | 169.7 (10) | O2A—N2—C5—C4 | −7.0 (11) |
C6—C7—C8—F2 | −94.5 (8) | O2A—N2—C5—C6 | 171.2 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—O2···H12B | 0.98 (1) | 2.68 (1) | 3.311 (3) | 123 (1) |
N2—O3···H13B | 0.98 (1) | 2.94 (1) | 3.844 (15) | 153 (1) |
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