Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229624000676/dg3049sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229624000676/dg3049Isup2.hkl | |
MDL mol file https://doi.org/10.1107/S2053229624000676/dg3049Isup3.mol | |
Chemical Markup Language (CML) file https://doi.org/10.1107/S2053229624000676/dg3049Isup4.cml |
CCDC reference: 2327307
C22H25BrFN4O2+·C17H19N2O5S−·C2H3N | Z = 2 |
Mr = 880.82 | F(000) = 916 |
Triclinic, P1 | Dx = 1.410 Mg m−3 |
a = 12.5755 (3) Å | Cu Kα radiation, λ = 1.54184 Å |
b = 12.6649 (3) Å | Cell parameters from 10183 reflections |
c = 14.4336 (2) Å | θ = 3.3–75.7° |
α = 68.909 (2)° | µ = 2.34 mm−1 |
β = 82.733 (2)° | T = 200 K |
γ = 75.557 (2)° | Block, clear light colourless |
V = 2075.30 (8) Å3 | 0.15 × 0.13 × 0.11 mm |
XtaLAB Synergy R, DW system, HyPix diffractometer | 8229 independent reflections |
Mirror monochromator | 6803 reflections with I > 2σ(I) |
Detector resolution: 10.0000 pixels mm-1 | Rint = 0.041 |
ω scans | θmax = 76.5°, θmin = 3.3° |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2022) | h = −13→15 |
Tmin = 0.650, Tmax = 1.000 | k = −15→15 |
23536 measured reflections | l = −17→18 |
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.053 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.156 | w = 1/[σ2(Fo2) + (0.0823P)2 + 1.8341P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
8229 reflections | Δρmax = 1.37 e Å−3 |
539 parameters | Δρmin = −0.69 e Å−3 |
0 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. |
x | y | z | Uiso*/Ueq | ||
Br1 | 0.67091 (4) | 1.46322 (4) | 0.55377 (3) | 0.06337 (16) | |
F1 | 0.90103 (16) | 1.06014 (18) | 0.56148 (14) | 0.0496 (5) | |
O6 | 0.9323 (2) | 0.8108 (2) | 0.17554 (16) | 0.0459 (5) | |
O7 | 0.94456 (17) | 0.59723 (18) | 0.28619 (15) | 0.0365 (4) | |
N3 | 0.7903 (2) | 1.0507 (2) | 0.40976 (17) | 0.0320 (5) | |
H3 | 0.807061 | 1.069170 | 0.345666 | 0.038* | |
N4 | 0.76464 (19) | 0.9065 (2) | 0.55885 (17) | 0.0328 (5) | |
N5 | 0.8055 (2) | 0.7049 (2) | 0.57422 (17) | 0.0354 (5) | |
N6 | 0.95552 (19) | 0.2753 (2) | 0.14596 (18) | 0.0300 (5) | |
H6 | 0.889 (4) | 0.269 (4) | 0.154 (3) | 0.052 (11)* | |
C18 | 0.7067 (3) | 1.3330 (3) | 0.5111 (2) | 0.0429 (7) | |
C19 | 0.6480 (3) | 1.3332 (3) | 0.4356 (2) | 0.0409 (7) | |
H19 | 0.591302 | 1.397893 | 0.404936 | 0.049* | |
C20 | 0.6741 (2) | 1.2371 (3) | 0.4062 (2) | 0.0358 (6) | |
H20 | 0.633732 | 1.235840 | 0.355338 | 0.043* | |
C21 | 0.7573 (2) | 1.1427 (2) | 0.44869 (19) | 0.0317 (6) | |
C22 | 0.8149 (3) | 1.1470 (3) | 0.5229 (2) | 0.0367 (6) | |
C23 | 0.7897 (3) | 1.2409 (3) | 0.5549 (2) | 0.0434 (7) | |
H23 | 0.829240 | 1.241816 | 0.606359 | 0.052* | |
C24 | 0.7980 (2) | 0.9368 (2) | 0.46350 (19) | 0.0284 (5) | |
C25 | 0.8389 (2) | 0.8517 (2) | 0.41621 (19) | 0.0286 (5) | |
C26 | 0.8414 (2) | 0.7361 (2) | 0.4753 (2) | 0.0305 (5) | |
C27 | 0.7704 (2) | 0.7918 (3) | 0.6073 (2) | 0.0353 (6) | |
H27 | 0.745294 | 0.771358 | 0.675044 | 0.042* | |
C28 | 0.8724 (2) | 0.8789 (2) | 0.3139 (2) | 0.0309 (6) | |
H28 | 0.872058 | 0.956977 | 0.273468 | 0.037* | |
C29 | 0.9052 (2) | 0.7924 (3) | 0.2739 (2) | 0.0319 (6) | |
C30 | 0.9103 (2) | 0.6745 (2) | 0.3346 (2) | 0.0313 (6) | |
C31 | 0.8797 (2) | 0.6469 (2) | 0.4339 (2) | 0.0327 (6) | |
H31 | 0.884361 | 0.568131 | 0.474730 | 0.039* | |
C32 | 0.8885 (5) | 0.9218 (4) | 0.1080 (3) | 0.0732 (14) | |
H32A | 0.810501 | 0.945709 | 0.125215 | 0.110* | |
H32B | 0.896514 | 0.919108 | 0.040431 | 0.110* | |
H32C | 0.928208 | 0.977652 | 0.111551 | 0.110* | |
C33 | 0.9330 (2) | 0.4798 (2) | 0.3374 (2) | 0.0329 (6) | |
H33A | 0.855364 | 0.478224 | 0.359140 | 0.039* | |
H33B | 0.978512 | 0.443442 | 0.396675 | 0.039* | |
C34 | 0.9713 (2) | 0.4156 (2) | 0.2642 (2) | 0.0287 (5) | |
H34 | 1.049267 | 0.420449 | 0.242716 | 0.034* | |
C35 | 0.9031 (2) | 0.4671 (3) | 0.1723 (2) | 0.0333 (6) | |
H35A | 0.904744 | 0.550146 | 0.139879 | 0.040* | |
H35B | 0.825777 | 0.461598 | 0.191882 | 0.040* | |
C36 | 0.9473 (2) | 0.4033 (2) | 0.0993 (2) | 0.0315 (6) | |
H36A | 0.898277 | 0.434511 | 0.042577 | 0.038* | |
H36B | 1.020925 | 0.417766 | 0.073219 | 0.038* | |
C37 | 1.0150 (2) | 0.2235 (2) | 0.2405 (2) | 0.0324 (6) | |
H37A | 1.093516 | 0.226082 | 0.225712 | 0.039* | |
H37B | 1.010312 | 0.141157 | 0.271879 | 0.039* | |
C38 | 0.9672 (2) | 0.2877 (2) | 0.3122 (2) | 0.0321 (6) | |
H38A | 1.009571 | 0.252661 | 0.373374 | 0.039* | |
H38B | 0.890098 | 0.280650 | 0.330846 | 0.039* | |
C39 | 1.0067 (3) | 0.2172 (3) | 0.0731 (2) | 0.0404 (7) | |
H39A | 1.009036 | 0.133850 | 0.102893 | 0.061* | |
H39B | 1.081577 | 0.229307 | 0.054918 | 0.061* | |
H39C | 0.963133 | 0.250061 | 0.013543 | 0.061* | |
S1 | 0.69507 (5) | 0.65651 (6) | 0.97649 (5) | 0.03338 (17) | |
O1 | 0.7221 (2) | 0.7233 (2) | 1.02794 (17) | 0.0484 (6) | |
O2 | 0.78010 (16) | 0.6105 (2) | 0.91622 (18) | 0.0454 (5) | |
O3 | 0.26954 (16) | 0.68389 (18) | 0.93466 (16) | 0.0391 (5) | |
O4 | 0.21762 (15) | 0.83186 (18) | 0.79706 (14) | 0.0341 (4) | |
O5 | 0.70675 (14) | 0.87738 (16) | 0.81418 (14) | 0.0284 (4) | |
N1 | 0.6492 (2) | 0.5500 (3) | 1.0531 (2) | 0.0413 (6) | |
H1A | 0.667 (3) | 0.486 (4) | 1.041 (3) | 0.045 (10)* | |
H1B | 0.601 (4) | 0.566 (4) | 1.090 (4) | 0.071 (15)* | |
N2 | 0.55352 (19) | 1.0113 (2) | 0.67886 (19) | 0.0371 (5) | |
H2 | 0.622464 | 1.017569 | 0.671753 | 0.044* | |
C1 | 0.5861 (2) | 0.7474 (2) | 0.89793 (19) | 0.0274 (5) | |
C2 | 0.4838 (2) | 0.7193 (2) | 0.90942 (19) | 0.0276 (5) | |
H2A | 0.470755 | 0.649943 | 0.959246 | 0.033* | |
C3 | 0.4009 (2) | 0.7946 (2) | 0.84654 (19) | 0.0265 (5) | |
C4 | 0.4219 (2) | 0.8931 (2) | 0.77032 (19) | 0.0279 (5) | |
H4 | 0.364685 | 0.943227 | 0.727626 | 0.033* | |
C5 | 0.5260 (2) | 0.9198 (2) | 0.75542 (19) | 0.0279 (5) | |
C6 | 0.6053 (2) | 0.8477 (2) | 0.82435 (19) | 0.0259 (5) | |
C7 | 0.2887 (2) | 0.7672 (2) | 0.8607 (2) | 0.0281 (5) | |
C8 | 0.7085 (2) | 0.9688 (2) | 0.8463 (2) | 0.0287 (5) | |
C9 | 0.6389 (3) | 0.9926 (3) | 0.9218 (3) | 0.0435 (7) | |
H9 | 0.585001 | 0.948438 | 0.952434 | 0.052* | |
C10 | 0.6489 (3) | 1.0820 (3) | 0.9522 (3) | 0.0507 (8) | |
H10 | 0.600481 | 1.099922 | 1.003214 | 0.061* | |
C11 | 0.7283 (3) | 1.1451 (3) | 0.9089 (3) | 0.0481 (8) | |
H11 | 0.735241 | 1.205418 | 0.930707 | 0.058* | |
C12 | 0.7976 (3) | 1.1199 (3) | 0.8339 (3) | 0.0451 (7) | |
H12 | 0.852416 | 1.162907 | 0.803943 | 0.054* | |
C13 | 0.7872 (2) | 1.0316 (3) | 0.8021 (2) | 0.0350 (6) | |
H13 | 0.834396 | 1.014837 | 0.750001 | 0.042* | |
C14 | 0.4764 (3) | 1.0987 (3) | 0.6087 (2) | 0.0405 (7) | |
H14A | 0.428723 | 1.060725 | 0.587578 | 0.049* | |
H14B | 0.517290 | 1.140348 | 0.549029 | 0.049* | |
C15 | 0.4046 (3) | 1.1863 (3) | 0.6551 (3) | 0.0599 (10) | |
H15A | 0.350000 | 1.241230 | 0.606449 | 0.072* | |
H15B | 0.363528 | 1.143640 | 0.714063 | 0.072* | |
C16 | 0.4657 (4) | 1.2545 (4) | 0.6859 (4) | 0.0672 (11) | |
H16A | 0.505029 | 1.299949 | 0.627186 | 0.081* | |
H16B | 0.520978 | 1.200671 | 0.734338 | 0.081* | |
C17 | 0.3891 (5) | 1.3354 (5) | 0.7321 (4) | 0.0852 (15) | |
H17A | 0.334052 | 1.388443 | 0.684379 | 0.128* | |
H17B | 0.431030 | 1.380109 | 0.750309 | 0.128* | |
H17C | 0.352130 | 1.290236 | 0.791745 | 0.128* | |
N7 | 0.5526 (5) | 0.4934 (7) | 0.8103 (6) | 0.147 (3) | |
C40 | 0.7623 (5) | 0.4550 (5) | 0.7872 (4) | 0.0795 (14) | |
H40A | 0.794289 | 0.451720 | 0.847001 | 0.119* | |
H40B | 0.783664 | 0.517287 | 0.729771 | 0.119* | |
H40C | 0.789371 | 0.380741 | 0.776201 | 0.119* | |
C41 | 0.6450 (6) | 0.4773 (6) | 0.8000 (4) | 0.0929 (19) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0945 (3) | 0.0491 (2) | 0.0617 (3) | −0.0288 (2) | 0.0219 (2) | −0.0364 (2) |
F1 | 0.0553 (11) | 0.0514 (11) | 0.0438 (10) | −0.0098 (9) | −0.0118 (8) | −0.0165 (9) |
O6 | 0.0671 (15) | 0.0393 (12) | 0.0308 (10) | −0.0120 (11) | 0.0130 (10) | −0.0163 (9) |
O7 | 0.0463 (11) | 0.0309 (10) | 0.0367 (10) | −0.0104 (9) | 0.0051 (9) | −0.0176 (9) |
N3 | 0.0442 (13) | 0.0302 (12) | 0.0245 (10) | −0.0100 (10) | 0.0034 (9) | −0.0131 (9) |
N4 | 0.0367 (12) | 0.0346 (13) | 0.0286 (11) | −0.0094 (10) | 0.0027 (9) | −0.0130 (10) |
N5 | 0.0458 (14) | 0.0334 (13) | 0.0282 (11) | −0.0108 (11) | −0.0003 (10) | −0.0108 (10) |
N6 | 0.0234 (11) | 0.0359 (13) | 0.0374 (12) | −0.0104 (9) | 0.0025 (9) | −0.0191 (10) |
C18 | 0.061 (2) | 0.0356 (16) | 0.0392 (16) | −0.0231 (15) | 0.0185 (14) | −0.0191 (13) |
C19 | 0.0459 (17) | 0.0356 (16) | 0.0420 (16) | −0.0136 (13) | 0.0108 (13) | −0.0151 (13) |
C20 | 0.0416 (15) | 0.0338 (15) | 0.0346 (14) | −0.0144 (12) | 0.0046 (12) | −0.0128 (12) |
C21 | 0.0405 (15) | 0.0319 (14) | 0.0254 (12) | −0.0160 (12) | 0.0070 (11) | −0.0103 (11) |
C22 | 0.0472 (16) | 0.0360 (15) | 0.0289 (13) | −0.0162 (13) | 0.0011 (12) | −0.0098 (12) |
C23 | 0.061 (2) | 0.0467 (18) | 0.0312 (14) | −0.0247 (16) | 0.0071 (13) | −0.0176 (13) |
C24 | 0.0273 (12) | 0.0316 (14) | 0.0278 (12) | −0.0078 (10) | −0.0006 (10) | −0.0113 (11) |
C25 | 0.0284 (12) | 0.0328 (14) | 0.0277 (12) | −0.0075 (11) | −0.0002 (10) | −0.0139 (11) |
C26 | 0.0300 (13) | 0.0329 (14) | 0.0282 (13) | −0.0060 (11) | −0.0033 (10) | −0.0098 (11) |
C27 | 0.0405 (15) | 0.0360 (15) | 0.0270 (13) | −0.0086 (12) | 0.0018 (11) | −0.0089 (11) |
C28 | 0.0352 (14) | 0.0302 (14) | 0.0291 (13) | −0.0119 (11) | 0.0026 (11) | −0.0105 (11) |
C29 | 0.0336 (14) | 0.0366 (15) | 0.0279 (13) | −0.0105 (12) | 0.0027 (10) | −0.0132 (11) |
C30 | 0.0307 (13) | 0.0322 (14) | 0.0364 (14) | −0.0071 (11) | −0.0003 (11) | −0.0185 (12) |
C31 | 0.0372 (14) | 0.0287 (14) | 0.0331 (14) | −0.0063 (11) | −0.0044 (11) | −0.0112 (11) |
C32 | 0.131 (4) | 0.047 (2) | 0.0298 (17) | −0.008 (2) | 0.014 (2) | −0.0132 (16) |
C33 | 0.0368 (14) | 0.0295 (14) | 0.0337 (14) | −0.0062 (11) | −0.0001 (11) | −0.0134 (11) |
C34 | 0.0274 (12) | 0.0291 (14) | 0.0316 (13) | −0.0054 (10) | −0.0019 (10) | −0.0131 (11) |
C35 | 0.0324 (14) | 0.0308 (14) | 0.0367 (14) | −0.0016 (11) | −0.0064 (11) | −0.0132 (12) |
C36 | 0.0318 (13) | 0.0335 (14) | 0.0310 (13) | −0.0086 (11) | −0.0050 (11) | −0.0110 (11) |
C37 | 0.0338 (14) | 0.0290 (14) | 0.0347 (14) | −0.0078 (11) | −0.0009 (11) | −0.0110 (11) |
C38 | 0.0335 (14) | 0.0318 (14) | 0.0306 (13) | −0.0086 (11) | 0.0016 (11) | −0.0102 (11) |
C39 | 0.0385 (15) | 0.0475 (18) | 0.0434 (16) | −0.0118 (13) | 0.0062 (13) | −0.0262 (14) |
S1 | 0.0252 (3) | 0.0334 (4) | 0.0369 (3) | −0.0073 (3) | −0.0053 (2) | −0.0045 (3) |
O1 | 0.0534 (13) | 0.0492 (13) | 0.0456 (12) | −0.0212 (11) | −0.0196 (10) | −0.0073 (10) |
O2 | 0.0251 (10) | 0.0432 (12) | 0.0543 (13) | −0.0019 (9) | 0.0035 (9) | −0.0060 (10) |
O3 | 0.0309 (10) | 0.0341 (11) | 0.0458 (12) | −0.0141 (8) | −0.0005 (9) | −0.0015 (9) |
O4 | 0.0276 (9) | 0.0439 (12) | 0.0308 (9) | −0.0135 (8) | −0.0028 (8) | −0.0085 (9) |
O5 | 0.0225 (8) | 0.0325 (10) | 0.0349 (9) | −0.0116 (7) | 0.0043 (7) | −0.0148 (8) |
N1 | 0.0384 (14) | 0.0341 (15) | 0.0422 (15) | −0.0066 (11) | −0.0002 (12) | −0.0036 (12) |
N2 | 0.0269 (11) | 0.0375 (13) | 0.0381 (13) | −0.0115 (10) | 0.0014 (9) | −0.0007 (11) |
C1 | 0.0251 (12) | 0.0278 (13) | 0.0295 (12) | −0.0052 (10) | −0.0011 (10) | −0.0106 (10) |
C2 | 0.0274 (12) | 0.0264 (13) | 0.0302 (13) | −0.0108 (10) | 0.0020 (10) | −0.0088 (10) |
C3 | 0.0266 (12) | 0.0287 (13) | 0.0283 (12) | −0.0107 (10) | 0.0018 (10) | −0.0127 (11) |
C4 | 0.0274 (12) | 0.0297 (13) | 0.0277 (12) | −0.0081 (10) | −0.0039 (10) | −0.0090 (11) |
C5 | 0.0287 (13) | 0.0269 (13) | 0.0278 (12) | −0.0093 (10) | 0.0031 (10) | −0.0082 (10) |
C6 | 0.0218 (11) | 0.0279 (13) | 0.0314 (12) | −0.0081 (10) | 0.0023 (9) | −0.0134 (11) |
C7 | 0.0289 (13) | 0.0286 (13) | 0.0308 (13) | −0.0099 (10) | 0.0012 (10) | −0.0134 (11) |
C8 | 0.0246 (12) | 0.0298 (13) | 0.0328 (13) | −0.0064 (10) | −0.0028 (10) | −0.0113 (11) |
C9 | 0.0417 (16) | 0.0490 (19) | 0.0491 (17) | −0.0189 (14) | 0.0113 (14) | −0.0262 (15) |
C10 | 0.059 (2) | 0.057 (2) | 0.0525 (19) | −0.0261 (17) | 0.0132 (16) | −0.0343 (17) |
C11 | 0.062 (2) | 0.0420 (18) | 0.0505 (19) | −0.0193 (16) | −0.0032 (16) | −0.0225 (15) |
C12 | 0.0514 (18) | 0.0367 (16) | 0.0500 (18) | −0.0213 (14) | −0.0023 (14) | −0.0101 (14) |
C13 | 0.0357 (14) | 0.0327 (15) | 0.0364 (14) | −0.0149 (12) | 0.0041 (11) | −0.0086 (12) |
C14 | 0.0371 (15) | 0.0423 (17) | 0.0351 (15) | −0.0154 (13) | −0.0049 (12) | 0.0006 (13) |
C15 | 0.0454 (19) | 0.045 (2) | 0.079 (3) | −0.0088 (16) | −0.0128 (18) | −0.0069 (19) |
C16 | 0.065 (3) | 0.062 (3) | 0.075 (3) | −0.018 (2) | −0.004 (2) | −0.022 (2) |
C17 | 0.114 (4) | 0.067 (3) | 0.076 (3) | −0.018 (3) | 0.017 (3) | −0.033 (3) |
N7 | 0.114 (4) | 0.238 (8) | 0.178 (6) | −0.108 (5) | 0.087 (4) | −0.161 (6) |
C40 | 0.103 (4) | 0.088 (4) | 0.066 (3) | −0.056 (3) | 0.007 (3) | −0.027 (3) |
C41 | 0.120 (5) | 0.121 (5) | 0.082 (3) | −0.083 (4) | 0.049 (3) | −0.068 (3) |
Br1—C18 | 1.896 (3) | C38—H38B | 0.9900 |
F1—C22 | 1.346 (4) | C39—H39A | 0.9800 |
O6—C29 | 1.366 (3) | C39—H39B | 0.9800 |
O6—C32 | 1.412 (5) | C39—H39C | 0.9800 |
O7—C30 | 1.355 (3) | S1—O1 | 1.429 (2) |
O7—C33 | 1.438 (3) | S1—O2 | 1.435 (2) |
N3—H3 | 0.8800 | S1—N1 | 1.591 (3) |
N3—C21 | 1.419 (3) | S1—C1 | 1.777 (3) |
N3—C24 | 1.355 (4) | O3—C7 | 1.250 (3) |
N4—C24 | 1.331 (3) | O4—C7 | 1.271 (3) |
N4—C27 | 1.355 (4) | O5—C6 | 1.394 (3) |
N5—C26 | 1.385 (4) | O5—C8 | 1.400 (3) |
N5—C27 | 1.310 (4) | N1—H1A | 0.86 (4) |
N6—H6 | 0.85 (4) | N1—H1B | 0.79 (5) |
N6—C36 | 1.497 (4) | N2—H2 | 0.8800 |
N6—C37 | 1.490 (4) | N2—C5 | 1.367 (3) |
N6—C39 | 1.487 (4) | N2—C14 | 1.448 (4) |
C18—C19 | 1.391 (5) | C1—C2 | 1.394 (4) |
C18—C23 | 1.370 (5) | C1—C6 | 1.384 (4) |
C19—H19 | 0.9500 | C2—H2A | 0.9500 |
C19—C20 | 1.380 (4) | C2—C3 | 1.392 (4) |
C20—H20 | 0.9500 | C3—C4 | 1.392 (4) |
C20—C21 | 1.383 (4) | C3—C7 | 1.508 (3) |
C21—C22 | 1.390 (4) | C4—H4 | 0.9500 |
C22—C23 | 1.377 (4) | C4—C5 | 1.403 (4) |
C23—H23 | 0.9500 | C5—C6 | 1.401 (4) |
C24—C25 | 1.434 (4) | C8—C9 | 1.380 (4) |
C25—C26 | 1.399 (4) | C8—C13 | 1.373 (4) |
C25—C28 | 1.423 (4) | C9—H9 | 0.9500 |
C26—C31 | 1.416 (4) | C9—C10 | 1.391 (5) |
C27—H27 | 0.9500 | C10—H10 | 0.9500 |
C28—H28 | 0.9500 | C10—C11 | 1.381 (5) |
C28—C29 | 1.368 (4) | C11—H11 | 0.9500 |
C29—C30 | 1.424 (4) | C11—C12 | 1.380 (5) |
C30—C31 | 1.375 (4) | C12—H12 | 0.9500 |
C31—H31 | 0.9500 | C12—C13 | 1.391 (4) |
C32—H32A | 0.9800 | C13—H13 | 0.9500 |
C32—H32B | 0.9800 | C14—H14A | 0.9900 |
C32—H32C | 0.9800 | C14—H14B | 0.9900 |
C33—H33A | 0.9900 | C14—C15 | 1.542 (6) |
C33—H33B | 0.9900 | C15—H15A | 0.9900 |
C33—C34 | 1.518 (4) | C15—H15B | 0.9900 |
C34—H34 | 1.0000 | C15—C16 | 1.492 (6) |
C34—C35 | 1.519 (4) | C16—H16A | 0.9900 |
C34—C38 | 1.527 (4) | C16—H16B | 0.9900 |
C35—H35A | 0.9900 | C16—C17 | 1.502 (7) |
C35—H35B | 0.9900 | C17—H17A | 0.9800 |
C35—C36 | 1.520 (4) | C17—H17B | 0.9800 |
C36—H36A | 0.9900 | C17—H17C | 0.9800 |
C36—H36B | 0.9900 | N7—C41 | 1.129 (8) |
C37—H37A | 0.9900 | C40—H40A | 0.9800 |
C37—H37B | 0.9900 | C40—H40B | 0.9800 |
C37—C38 | 1.516 (4) | C40—H40C | 0.9800 |
C38—H38A | 0.9900 | C40—C41 | 1.432 (8) |
C29—O6—C32 | 116.7 (2) | C37—C38—C34 | 110.1 (2) |
C30—O7—C33 | 118.1 (2) | C37—C38—H38A | 109.6 |
C21—N3—H3 | 117.4 | C37—C38—H38B | 109.6 |
C24—N3—H3 | 117.4 | H38A—C38—H38B | 108.1 |
C24—N3—C21 | 125.1 (2) | N6—C39—H39A | 109.5 |
C24—N4—C27 | 116.2 (2) | N6—C39—H39B | 109.5 |
C27—N5—C26 | 114.7 (2) | N6—C39—H39C | 109.5 |
C36—N6—H6 | 103 (3) | H39A—C39—H39B | 109.5 |
C37—N6—H6 | 113 (3) | H39A—C39—H39C | 109.5 |
C37—N6—C36 | 112.9 (2) | H39B—C39—H39C | 109.5 |
C39—N6—H6 | 106 (3) | O1—S1—O2 | 117.84 (15) |
C39—N6—C36 | 109.7 (2) | O1—S1—N1 | 110.14 (16) |
C39—N6—C37 | 111.6 (2) | O1—S1—C1 | 106.95 (13) |
C19—C18—Br1 | 119.1 (3) | O2—S1—N1 | 106.94 (16) |
C23—C18—Br1 | 119.6 (3) | O2—S1—C1 | 107.57 (13) |
C23—C18—C19 | 121.4 (3) | N1—S1—C1 | 106.90 (14) |
C18—C19—H19 | 120.8 | C6—O5—C8 | 115.58 (19) |
C20—C19—C18 | 118.4 (3) | S1—N1—H1A | 117 (3) |
C20—C19—H19 | 120.8 | S1—N1—H1B | 115 (4) |
C19—C20—H20 | 119.1 | H1A—N1—H1B | 126 (4) |
C19—C20—C21 | 121.8 (3) | C5—N2—H2 | 117.9 |
C21—C20—H20 | 119.1 | C5—N2—C14 | 124.1 (2) |
C20—C21—N3 | 120.5 (3) | C14—N2—H2 | 117.9 |
C20—C21—C22 | 117.8 (3) | C2—C1—S1 | 121.3 (2) |
C22—C21—N3 | 121.3 (3) | C6—C1—S1 | 118.17 (19) |
F1—C22—C21 | 119.5 (3) | C6—C1—C2 | 120.5 (2) |
F1—C22—C23 | 118.7 (3) | C1—C2—H2A | 120.6 |
C23—C22—C21 | 121.7 (3) | C3—C2—C1 | 118.8 (2) |
C18—C23—C22 | 118.9 (3) | C3—C2—H2A | 120.6 |
C18—C23—H23 | 120.6 | C2—C3—C7 | 119.2 (2) |
C22—C23—H23 | 120.6 | C4—C3—C2 | 120.5 (2) |
N3—C24—C25 | 119.6 (2) | C4—C3—C7 | 120.3 (2) |
N4—C24—N3 | 119.1 (2) | C3—C4—H4 | 119.4 |
N4—C24—C25 | 121.3 (3) | C3—C4—C5 | 121.2 (2) |
C26—C25—C24 | 116.6 (2) | C5—C4—H4 | 119.4 |
C26—C25—C28 | 119.4 (2) | N2—C5—C4 | 124.0 (2) |
C28—C25—C24 | 124.0 (3) | N2—C5—C6 | 118.7 (2) |
N5—C26—C25 | 122.0 (2) | C6—C5—C4 | 117.2 (2) |
N5—C26—C31 | 117.9 (3) | O5—C6—C5 | 117.9 (2) |
C25—C26—C31 | 120.1 (2) | C1—C6—O5 | 120.6 (2) |
N4—C27—H27 | 115.4 | C1—C6—C5 | 121.5 (2) |
N5—C27—N4 | 129.3 (3) | O3—C7—O4 | 123.3 (2) |
N5—C27—H27 | 115.4 | O3—C7—C3 | 118.9 (2) |
C25—C28—H28 | 120.0 | O4—C7—C3 | 117.8 (2) |
C29—C28—C25 | 120.0 (3) | C9—C8—O5 | 122.5 (2) |
C29—C28—H28 | 120.0 | C13—C8—O5 | 116.6 (2) |
O6—C29—C28 | 124.2 (3) | C13—C8—C9 | 120.9 (3) |
O6—C29—C30 | 115.2 (2) | C8—C9—H9 | 120.5 |
C28—C29—C30 | 120.6 (2) | C8—C9—C10 | 119.0 (3) |
O7—C30—C29 | 114.8 (2) | C10—C9—H9 | 120.5 |
O7—C30—C31 | 125.2 (3) | C9—C10—H10 | 119.6 |
C31—C30—C29 | 120.0 (2) | C11—C10—C9 | 120.7 (3) |
C26—C31—H31 | 120.0 | C11—C10—H10 | 119.6 |
C30—C31—C26 | 119.9 (3) | C10—C11—H11 | 120.2 |
C30—C31—H31 | 120.0 | C12—C11—C10 | 119.5 (3) |
O6—C32—H32A | 109.5 | C12—C11—H11 | 120.2 |
O6—C32—H32B | 109.5 | C11—C12—H12 | 119.9 |
O6—C32—H32C | 109.5 | C11—C12—C13 | 120.2 (3) |
H32A—C32—H32B | 109.5 | C13—C12—H12 | 119.9 |
H32A—C32—H32C | 109.5 | C8—C13—C12 | 119.8 (3) |
H32B—C32—H32C | 109.5 | C8—C13—H13 | 120.1 |
O7—C33—H33A | 110.4 | C12—C13—H13 | 120.1 |
O7—C33—H33B | 110.4 | N2—C14—H14A | 109.4 |
O7—C33—C34 | 106.6 (2) | N2—C14—H14B | 109.4 |
H33A—C33—H33B | 108.6 | N2—C14—C15 | 111.1 (3) |
C34—C33—H33A | 110.4 | H14A—C14—H14B | 108.0 |
C34—C33—H33B | 110.4 | C15—C14—H14A | 109.4 |
C33—C34—H34 | 108.3 | C15—C14—H14B | 109.4 |
C33—C34—C35 | 112.5 (2) | C14—C15—H15A | 108.5 |
C33—C34—C38 | 111.2 (2) | C14—C15—H15B | 108.5 |
C35—C34—H34 | 108.3 | H15A—C15—H15B | 107.5 |
C35—C34—C38 | 108.2 (2) | C16—C15—C14 | 115.2 (3) |
C38—C34—H34 | 108.3 | C16—C15—H15A | 108.5 |
C34—C35—H35A | 109.5 | C16—C15—H15B | 108.5 |
C34—C35—H35B | 109.5 | C15—C16—H16A | 109.4 |
C34—C35—C36 | 110.7 (2) | C15—C16—H16B | 109.4 |
H35A—C35—H35B | 108.1 | C15—C16—C17 | 111.2 (4) |
C36—C35—H35A | 109.5 | H16A—C16—H16B | 108.0 |
C36—C35—H35B | 109.5 | C17—C16—H16A | 109.4 |
N6—C36—C35 | 112.4 (2) | C17—C16—H16B | 109.4 |
N6—C36—H36A | 109.1 | C16—C17—H17A | 109.5 |
N6—C36—H36B | 109.1 | C16—C17—H17B | 109.5 |
C35—C36—H36A | 109.1 | C16—C17—H17C | 109.5 |
C35—C36—H36B | 109.1 | H17A—C17—H17B | 109.5 |
H36A—C36—H36B | 107.9 | H17A—C17—H17C | 109.5 |
N6—C37—H37A | 109.3 | H17B—C17—H17C | 109.5 |
N6—C37—H37B | 109.3 | H40A—C40—H40B | 109.5 |
N6—C37—C38 | 111.5 (2) | H40A—C40—H40C | 109.5 |
H37A—C37—H37B | 108.0 | H40B—C40—H40C | 109.5 |
C38—C37—H37A | 109.3 | C41—C40—H40A | 109.5 |
C38—C37—H37B | 109.3 | C41—C40—H40B | 109.5 |
C34—C38—H38A | 109.6 | C41—C40—H40C | 109.5 |
C34—C38—H38B | 109.6 | N7—C41—C40 | 179.0 (6) |
Br1—C18—C19—C20 | −179.2 (2) | C33—C34—C38—C37 | −175.1 (2) |
Br1—C18—C23—C22 | −179.9 (2) | C34—C35—C36—N6 | 54.6 (3) |
F1—C22—C23—C18 | 175.7 (3) | C35—C34—C38—C37 | 60.8 (3) |
O6—C29—C30—O7 | 1.9 (4) | C36—N6—C37—C38 | 52.4 (3) |
O6—C29—C30—C31 | −177.0 (3) | C37—N6—C36—C35 | −50.8 (3) |
O7—C30—C31—C26 | −177.6 (2) | C38—C34—C35—C36 | −59.1 (3) |
O7—C33—C34—C35 | −60.8 (3) | C39—N6—C36—C35 | −175.9 (2) |
O7—C33—C34—C38 | 177.6 (2) | C39—N6—C37—C38 | 176.4 (2) |
N3—C21—C22—F1 | −2.6 (4) | S1—C1—C2—C3 | 179.1 (2) |
N3—C21—C22—C23 | 174.0 (3) | S1—C1—C6—O5 | −1.5 (3) |
N3—C24—C25—C26 | −178.0 (2) | S1—C1—C6—C5 | 175.7 (2) |
N3—C24—C25—C28 | −0.3 (4) | O1—S1—C1—C2 | −118.4 (2) |
N4—C24—C25—C26 | 0.2 (4) | O1—S1—C1—C6 | 61.7 (2) |
N4—C24—C25—C28 | 177.9 (3) | O2—S1—C1—C2 | 114.1 (2) |
N5—C26—C31—C30 | 176.3 (3) | O2—S1—C1—C6 | −65.8 (2) |
N6—C37—C38—C34 | −57.8 (3) | O5—C8—C9—C10 | 177.4 (3) |
C18—C19—C20—C21 | −1.0 (4) | O5—C8—C13—C12 | −176.7 (3) |
C19—C18—C23—C22 | −0.1 (5) | N1—S1—C1—C2 | −0.4 (3) |
C19—C20—C21—N3 | −173.1 (3) | N1—S1—C1—C6 | 179.6 (2) |
C19—C20—C21—C22 | 0.0 (4) | N2—C5—C6—O5 | 3.6 (4) |
C20—C21—C22—F1 | −175.7 (2) | N2—C5—C6—C1 | −173.8 (3) |
C20—C21—C22—C23 | 0.9 (4) | N2—C14—C15—C16 | 61.9 (4) |
C21—N3—C24—N4 | 5.5 (4) | C1—C2—C3—C4 | 3.3 (4) |
C21—N3—C24—C25 | −176.2 (2) | C1—C2—C3—C7 | −177.8 (2) |
C21—C22—C23—C18 | −0.9 (4) | C2—C1—C6—O5 | 178.5 (2) |
C23—C18—C19—C20 | 1.0 (4) | C2—C1—C6—C5 | −4.2 (4) |
C24—N3—C21—C20 | −127.7 (3) | C2—C3—C4—C5 | −0.7 (4) |
C24—N3—C21—C22 | 59.4 (4) | C2—C3—C7—O3 | 7.2 (4) |
C24—N4—C27—N5 | 0.9 (5) | C2—C3—C7—O4 | −174.0 (2) |
C24—C25—C26—N5 | 0.5 (4) | C3—C4—C5—N2 | 176.2 (3) |
C24—C25—C26—C31 | 179.5 (2) | C3—C4—C5—C6 | −4.3 (4) |
C24—C25—C28—C29 | −176.7 (3) | C4—C3—C7—O3 | −174.0 (3) |
C25—C26—C31—C30 | −2.7 (4) | C4—C3—C7—O4 | 4.8 (4) |
C25—C28—C29—O6 | 175.8 (3) | C4—C5—C6—O5 | −176.0 (2) |
C25—C28—C29—C30 | −2.5 (4) | C4—C5—C6—C1 | 6.7 (4) |
C26—N5—C27—N4 | −0.2 (5) | C5—N2—C14—C15 | 77.1 (4) |
C26—C25—C28—C29 | 0.9 (4) | C6—O5—C8—C9 | 29.6 (4) |
C27—N4—C24—N3 | 177.4 (2) | C6—O5—C8—C13 | −153.5 (2) |
C27—N4—C24—C25 | −0.8 (4) | C6—C1—C2—C3 | −0.9 (4) |
C27—N5—C26—C25 | −0.5 (4) | C7—C3—C4—C5 | −179.5 (2) |
C27—N5—C26—C31 | −179.5 (3) | C8—O5—C6—C1 | −106.0 (3) |
C28—C25—C26—N5 | −177.3 (2) | C8—O5—C6—C5 | 76.6 (3) |
C28—C25—C26—C31 | 1.7 (4) | C8—C9—C10—C11 | −1.1 (6) |
C28—C29—C30—O7 | −179.6 (2) | C9—C8—C13—C12 | 0.4 (5) |
C28—C29—C30—C31 | 1.5 (4) | C9—C10—C11—C12 | 0.8 (6) |
C29—C30—C31—C26 | 1.1 (4) | C10—C11—C12—C13 | 0.1 (5) |
C30—O7—C33—C34 | 176.8 (2) | C11—C12—C13—C8 | −0.7 (5) |
C32—O6—C29—C28 | −22.9 (5) | C13—C8—C9—C10 | 0.5 (5) |
C32—O6—C29—C30 | 155.5 (3) | C14—N2—C5—C4 | 6.0 (5) |
C33—O7—C30—C29 | −168.9 (2) | C14—N2—C5—C6 | −173.5 (3) |
C33—O7—C30—C31 | 9.9 (4) | C14—C15—C16—C17 | −178.8 (4) |
C33—C34—C35—C36 | 177.6 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O3i | 0.86 (4) | 2.02 (5) | 2.830 (4) | 158 (4) |
N1—H1B···N7i | 0.79 (5) | 2.37 (5) | 3.046 (8) | 144 (5) |
N3—H3···O4ii | 0.88 | 2..01 | 2.818 (3) | 153 |
N6—H6···O3iii | 0.85 (5) | 2.34 (5) | 3.050 (3) | 142 (4) |
N6—H6···O4iii | 0.85 (5) | 1.97 (5) | 2.734 (3) | 149 (5) |
Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1. |
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