Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100014190/qa0431sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100014190/qa0431Isup2.hkl |
CCDC reference: 153959
Data collection: DENZO (Otwinowski & Minor, 1997) and COLLECT (Hooft, 1998); cell refinement: DENZO and COLLECT; data reduction: DENZO and COLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.
C5H4Cl2N2S | F(000) = 1176 |
Mr = 195.07 | Dx = 1.666 Mg m−3 |
Triclinic, P1 | Melting point: 305 - 311 K K |
a = 13.6482 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 14.1294 (2) Å | Cell parameters from 15842 reflections |
c = 14.1343 (2) Å | θ = 2.9–27.5° |
α = 119.9578 (7)° | µ = 1.02 mm−1 |
β = 95.9391 (6)° | T = 150 K |
γ = 92.8349 (7)° | Block, yellow |
V = 2332.60 (6) Å3 | 0.30 × 0.13 × 0.13 mm |
Z = 12 |
Enraf Nonius KappaCCD area-detector diffractometer | 10671 independent reflections |
Radiation source: Enraf Nonius FR591 rotating anode | 8028 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
Detector resolution: 9.091 pixels mm-1 | θmax = 27.5°, θmin = 2.9° |
φ and ω scans | h = −17→17 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −18→18 |
Tmin = 0.749, Tmax = 0.883 | l = −18→18 |
34427 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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0491P)2 + 0.2046P] where P = (Fo2 + 2Fc2)/3 |
10671 reflections | (Δ/σ)max = 0.029 |
547 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.47 e Å−3 |
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. |
x | y | z | Uiso*/Ueq | ||
N1A | 0.38534 (10) | 0.20309 (12) | 0.45142 (12) | 0.0238 (3) | |
C2A | 0.39314 (12) | 0.23552 (15) | 0.37786 (15) | 0.0232 (4) | |
S21A | 0.39650 (4) | 0.37482 (4) | 0.41972 (4) | 0.02945 (12) | |
C22A | 0.38244 (14) | 0.43636 (16) | 0.56270 (16) | 0.0337 (5) | |
H21A | 0.3199 | 0.4044 | 0.5692 | 0.042* | |
H22A | 0.3818 | 0.5159 | 0.5948 | 0.042* | |
H23A | 0.4379 | 0.4224 | 0.6022 | 0.042* | |
N3A | 0.39832 (11) | 0.17091 (13) | 0.26982 (13) | 0.0263 (4) | |
C4A | 0.39408 (13) | 0.06466 (16) | 0.23484 (15) | 0.0256 (4) | |
Cl4A | 0.39692 (4) | −0.02227 (4) | 0.09511 (4) | 0.03840 (13) | |
C5A | 0.38798 (13) | 0.01918 (16) | 0.30139 (15) | 0.0261 (4) | |
H5A | 0.3869 | −0.0574 | 0.2745 | 0.033* | |
C6A | 0.38369 (12) | 0.09512 (16) | 0.40987 (15) | 0.0241 (4) | |
Cl6A | 0.37358 (4) | 0.04948 (4) | 0.50201 (4) | 0.03126 (12) | |
N1B | 0.37395 (10) | −0.64194 (13) | −0.05875 (12) | 0.0240 (3) | |
C2B | 0.36984 (12) | −0.56773 (16) | 0.04714 (15) | 0.0247 (4) | |
S21B | 0.36834 (4) | −0.60995 (5) | 0.14405 (4) | 0.03389 (13) | |
C22B | 0.37360 (15) | −0.75550 (17) | 0.06153 (17) | 0.0358 (5) | |
H21B | 0.3144 | −0.7894 | 0.0054 | 0.045* | |
H22B | 0.3762 | −0.7878 | 0.1089 | 0.045* | |
H23B | 0.4330 | −0.7686 | 0.0253 | 0.045* | |
N3B | 0.36811 (11) | −0.45863 (13) | 0.09106 (12) | 0.0265 (4) | |
C4B | 0.37426 (13) | −0.42366 (16) | 0.02107 (15) | 0.0252 (4) | |
Cl4B | 0.37424 (4) | −0.28314 (4) | 0.07432 (4) | 0.03737 (13) | |
C5B | 0.38106 (12) | −0.48975 (16) | −0.08984 (15) | 0.0259 (4) | |
H5B | 0.3862 | −0.4618 | −0.1381 | 0.032* | |
C6B | 0.37965 (12) | −0.59970 (16) | −0.12390 (14) | 0.0240 (4) | |
Cl6B | 0.38529 (4) | −0.69211 (4) | −0.26081 (4) | 0.03322 (12) | |
N1C | 0.36536 (10) | −0.13544 (13) | 0.60558 (12) | 0.0244 (3) | |
C2C | 0.36130 (12) | −0.24285 (16) | 0.57346 (15) | 0.0244 (4) | |
S21C | 0.35783 (4) | −0.34074 (4) | 0.43411 (4) | 0.03170 (13) | |
C22C | 0.36817 (15) | −0.25618 (18) | 0.37330 (16) | 0.0357 (5) | |
H21C | 0.3135 | −0.2105 | 0.3891 | 0.045* | |
H22C | 0.3651 | −0.3031 | 0.2932 | 0.045* | |
H23C | 0.4316 | −0.2088 | 0.4043 | 0.045* | |
N3C | 0.35872 (10) | −0.28674 (13) | 0.63869 (13) | 0.0258 (3) | |
C4C | 0.35788 (12) | −0.21496 (16) | 0.74394 (15) | 0.0248 (4) | |
Cl4C | 0.35552 (4) | −0.26781 (4) | 0.83095 (4) | 0.03655 (13) | |
C5C | 0.35842 (13) | −0.10257 (16) | 0.78816 (15) | 0.0267 (4) | |
H5C | 0.3560 | −0.0530 | 0.8641 | 0.033* | |
C6C | 0.36282 (13) | −0.06935 (15) | 0.71234 (15) | 0.0245 (4) | |
Cl6C | 0.36721 (4) | 0.06942 (4) | 0.75702 (4) | 0.03605 (13) | |
N1D | −0.13026 (10) | 0.57481 (13) | 0.10062 (12) | 0.0238 (3) | |
C2D | −0.12170 (12) | 0.60705 (16) | 0.02722 (15) | 0.0245 (4) | |
S21D | −0.11406 (4) | 0.74656 (4) | 0.06969 (4) | 0.03232 (13) | |
C22D | −0.12531 (15) | 0.80767 (17) | 0.21327 (17) | 0.0377 (5) | |
H21D | −0.1892 | 0.7793 | 0.2209 | 0.047* | |
H22D | −0.1216 | 0.8877 | 0.2469 | 0.047* | |
H23D | −0.0713 | 0.7894 | 0.2505 | 0.047* | |
N3D | −0.11544 (11) | 0.54151 (14) | −0.08108 (13) | 0.0265 (4) | |
C4D | −0.11707 (12) | 0.43629 (16) | −0.11474 (14) | 0.0249 (4) | |
Cl4D | −0.10867 (4) | 0.34975 (4) | −0.25278 (4) | 0.03609 (13) | |
C5D | −0.12364 (12) | 0.39137 (16) | −0.04771 (15) | 0.0250 (4) | |
H5D | −0.1238 | 0.3150 | −0.0740 | 0.031* | |
C6D | −0.12989 (12) | 0.46759 (16) | 0.06058 (15) | 0.0240 (4) | |
Cl6D | −0.13668 (4) | 0.42284 (4) | 0.15354 (4) | 0.03442 (13) | |
N1E | −0.13631 (10) | −0.26910 (13) | −0.40530 (12) | 0.0245 (3) | |
C2E | −0.14368 (12) | −0.19540 (16) | −0.30031 (14) | 0.0230 (4) | |
S21E | −0.14966 (4) | −0.23771 (4) | −0.20408 (4) | 0.03033 (12) | |
C22E | −0.13719 (15) | −0.38207 (17) | −0.28445 (17) | 0.0351 (5) | |
H21E | −0.1920 | −0.4185 | −0.3459 | 0.044* | |
H22E | −0.1387 | −0.4148 | −0.2376 | 0.044* | |
H23E | −0.0740 | −0.3915 | −0.3136 | 0.044* | |
N3E | −0.14731 (11) | −0.08639 (13) | −0.25718 (12) | 0.0261 (4) | |
C4E | −0.14168 (13) | −0.05132 (16) | −0.32751 (16) | 0.0262 (4) | |
Cl4E | −0.14325 (4) | 0.08865 (4) | −0.27476 (4) | 0.03697 (13) | |
C5E | −0.13493 (13) | −0.11798 (16) | −0.43852 (15) | 0.0266 (4) | |
H5E | −0.1320 | −0.0907 | −0.4876 | 0.033* | |
C6E | −0.13288 (13) | −0.22724 (16) | −0.47106 (14) | 0.0237 (4) | |
Cl6E | −0.12455 (4) | −0.31956 (4) | −0.60781 (4) | 0.03154 (12) | |
N1F | −0.11133 (10) | 1.24180 (13) | 0.26273 (12) | 0.0245 (3) | |
C2F | −0.10841 (13) | 1.13584 (16) | 0.23193 (15) | 0.0248 (4) | |
S21F | −0.10814 (4) | 1.03782 (4) | 0.09317 (4) | 0.03462 (13) | |
C22F | −0.11303 (15) | 1.12010 (18) | 0.02900 (16) | 0.0365 (5) | |
H21F | −0.1713 | 1.1603 | 0.0461 | 0.046* | |
H22F | −0.1177 | 1.0723 | −0.0512 | 0.046* | |
H23F | −0.0528 | 1.1725 | 0.0571 | 0.046* | |
N3F | −0.10731 (11) | 1.09240 (13) | 0.29836 (13) | 0.0267 (4) | |
C4F | −0.11196 (13) | 1.16331 (16) | 0.40246 (16) | 0.0258 (4) | |
Cl4F | −0.11438 (4) | 1.11032 (5) | 0.48962 (4) | 0.03747 (13) | |
C5F | −0.11586 (13) | 1.27476 (16) | 0.44580 (15) | 0.0254 (4) | |
H5F | −0.1186 | 1.3241 | 0.5217 | 0.032* | |
C6F | −0.11542 (12) | 1.30811 (15) | 0.36917 (15) | 0.0239 (4) | |
Cl6F | −0.12257 (4) | 1.44450 (4) | 0.41160 (4) | 0.03168 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.0251 (8) | 0.0201 (9) | 0.0270 (8) | 0.0024 (6) | 0.0041 (6) | 0.0126 (7) |
C2A | 0.0194 (9) | 0.0224 (10) | 0.0297 (10) | 0.0035 (7) | 0.0037 (7) | 0.0146 (9) |
S21A | 0.0365 (3) | 0.0213 (3) | 0.0351 (3) | 0.0040 (2) | 0.0074 (2) | 0.0172 (2) |
C22A | 0.0405 (11) | 0.0214 (11) | 0.0359 (12) | 0.0054 (8) | 0.0108 (9) | 0.0111 (9) |
N3A | 0.0273 (8) | 0.0264 (10) | 0.0270 (9) | 0.0024 (7) | 0.0036 (6) | 0.0150 (8) |
C4A | 0.0253 (9) | 0.0276 (11) | 0.0210 (9) | 0.0030 (8) | 0.0023 (7) | 0.0104 (9) |
Cl4A | 0.0549 (3) | 0.0325 (3) | 0.0210 (3) | 0.0026 (2) | 0.0046 (2) | 0.0090 (2) |
C5A | 0.0313 (10) | 0.0184 (10) | 0.0284 (10) | 0.0036 (8) | 0.0052 (8) | 0.0115 (9) |
C6A | 0.0234 (9) | 0.0252 (11) | 0.0272 (10) | 0.0025 (7) | 0.0035 (7) | 0.0159 (9) |
Cl6A | 0.0453 (3) | 0.0261 (3) | 0.0281 (3) | 0.0051 (2) | 0.0070 (2) | 0.0177 (2) |
N1B | 0.0259 (8) | 0.0231 (9) | 0.0247 (8) | 0.0038 (6) | 0.0050 (6) | 0.0131 (7) |
C2B | 0.0226 (9) | 0.0298 (11) | 0.0232 (10) | 0.0038 (7) | 0.0042 (7) | 0.0145 (9) |
S21B | 0.0459 (3) | 0.0367 (3) | 0.0258 (3) | 0.0084 (2) | 0.0088 (2) | 0.0199 (2) |
C22B | 0.0464 (12) | 0.0361 (13) | 0.0365 (12) | 0.0099 (10) | 0.0077 (9) | 0.0261 (11) |
N3B | 0.0287 (8) | 0.0256 (9) | 0.0239 (8) | 0.0028 (7) | 0.0034 (6) | 0.0118 (7) |
C4B | 0.0241 (9) | 0.0211 (10) | 0.0285 (10) | 0.0021 (7) | 0.0036 (7) | 0.0113 (9) |
Cl4B | 0.0513 (3) | 0.0205 (3) | 0.0366 (3) | 0.0035 (2) | 0.0083 (2) | 0.0115 (2) |
C5B | 0.0286 (10) | 0.0249 (11) | 0.0298 (10) | 0.0026 (8) | 0.0056 (8) | 0.0179 (9) |
C6B | 0.0243 (9) | 0.0255 (11) | 0.0208 (9) | 0.0034 (7) | 0.0030 (7) | 0.0107 (8) |
Cl6B | 0.0492 (3) | 0.0269 (3) | 0.0228 (2) | 0.0067 (2) | 0.0106 (2) | 0.0110 (2) |
N1C | 0.0257 (8) | 0.0230 (9) | 0.0249 (8) | 0.0045 (6) | 0.0047 (6) | 0.0122 (7) |
C2C | 0.0197 (9) | 0.0259 (11) | 0.0266 (10) | 0.0038 (7) | 0.0040 (7) | 0.0123 (9) |
S21C | 0.0383 (3) | 0.0243 (3) | 0.0245 (3) | 0.0034 (2) | 0.0042 (2) | 0.0066 (2) |
C22C | 0.0402 (11) | 0.0372 (13) | 0.0232 (10) | 0.0008 (9) | 0.0051 (8) | 0.0108 (10) |
N3C | 0.0236 (8) | 0.0247 (9) | 0.0292 (9) | 0.0026 (6) | 0.0036 (6) | 0.0140 (8) |
C4C | 0.0231 (9) | 0.0282 (11) | 0.0301 (11) | 0.0033 (8) | 0.0037 (7) | 0.0199 (9) |
Cl4C | 0.0475 (3) | 0.0368 (3) | 0.0366 (3) | 0.0055 (2) | 0.0067 (2) | 0.0268 (3) |
C5C | 0.0295 (10) | 0.0279 (11) | 0.0237 (10) | 0.0066 (8) | 0.0076 (7) | 0.0128 (9) |
C6C | 0.0275 (9) | 0.0203 (10) | 0.0265 (10) | 0.0068 (7) | 0.0056 (7) | 0.0118 (9) |
Cl6C | 0.0580 (3) | 0.0212 (3) | 0.0310 (3) | 0.0112 (2) | 0.0109 (2) | 0.0135 (2) |
N1D | 0.0251 (8) | 0.0225 (9) | 0.0248 (8) | 0.0027 (6) | 0.0046 (6) | 0.0125 (7) |
C2D | 0.0203 (9) | 0.0254 (11) | 0.0303 (10) | 0.0025 (7) | 0.0037 (7) | 0.0161 (9) |
S21D | 0.0389 (3) | 0.0245 (3) | 0.0385 (3) | 0.0032 (2) | 0.0065 (2) | 0.0195 (2) |
C22D | 0.0438 (12) | 0.0229 (11) | 0.0413 (13) | 0.0042 (9) | 0.0093 (9) | 0.0119 (10) |
N3D | 0.0251 (8) | 0.0301 (10) | 0.0280 (9) | 0.0029 (7) | 0.0034 (6) | 0.0175 (8) |
C4D | 0.0228 (9) | 0.0291 (11) | 0.0217 (10) | 0.0038 (8) | 0.0037 (7) | 0.0120 (9) |
Cl4D | 0.0454 (3) | 0.0366 (3) | 0.0208 (2) | 0.0052 (2) | 0.0049 (2) | 0.0105 (2) |
C5D | 0.0268 (9) | 0.0215 (10) | 0.0263 (10) | 0.0039 (7) | 0.0043 (7) | 0.0116 (9) |
C6D | 0.0241 (9) | 0.0263 (11) | 0.0254 (10) | 0.0023 (7) | 0.0029 (7) | 0.0160 (9) |
Cl6D | 0.0536 (3) | 0.0286 (3) | 0.0275 (3) | 0.0057 (2) | 0.0082 (2) | 0.0185 (2) |
N1E | 0.0243 (8) | 0.0267 (9) | 0.0249 (8) | 0.0026 (6) | 0.0043 (6) | 0.0147 (7) |
C2E | 0.0218 (9) | 0.0281 (11) | 0.0219 (9) | 0.0021 (7) | 0.0023 (7) | 0.0150 (9) |
S21E | 0.0379 (3) | 0.0350 (3) | 0.0241 (3) | 0.0066 (2) | 0.0078 (2) | 0.0187 (2) |
C22E | 0.0452 (12) | 0.0349 (13) | 0.0373 (12) | 0.0103 (9) | 0.0108 (9) | 0.0259 (11) |
N3E | 0.0260 (8) | 0.0268 (9) | 0.0247 (8) | 0.0026 (6) | 0.0040 (6) | 0.0125 (7) |
C4E | 0.0253 (9) | 0.0216 (10) | 0.0303 (10) | 0.0019 (7) | 0.0036 (7) | 0.0124 (9) |
Cl4E | 0.0495 (3) | 0.0198 (3) | 0.0370 (3) | 0.0008 (2) | 0.0062 (2) | 0.0113 (2) |
C5E | 0.0298 (10) | 0.0275 (11) | 0.0270 (10) | 0.0030 (8) | 0.0047 (8) | 0.0171 (9) |
C6E | 0.0244 (9) | 0.0268 (11) | 0.0218 (9) | 0.0046 (7) | 0.0049 (7) | 0.0133 (9) |
Cl6E | 0.0466 (3) | 0.0270 (3) | 0.0206 (2) | 0.0059 (2) | 0.00906 (19) | 0.0110 (2) |
N1F | 0.0264 (8) | 0.0258 (9) | 0.0212 (8) | 0.0046 (6) | 0.0037 (6) | 0.0115 (7) |
C2F | 0.0249 (9) | 0.0231 (11) | 0.0240 (10) | 0.0026 (7) | 0.0044 (7) | 0.0100 (9) |
S21F | 0.0483 (3) | 0.0251 (3) | 0.0237 (3) | 0.0072 (2) | 0.0071 (2) | 0.0068 (2) |
C22F | 0.0489 (12) | 0.0372 (13) | 0.0218 (10) | 0.0085 (10) | 0.0055 (9) | 0.0133 (10) |
N3F | 0.0306 (8) | 0.0233 (9) | 0.0262 (9) | 0.0043 (7) | 0.0057 (6) | 0.0122 (8) |
C4F | 0.0222 (9) | 0.0298 (11) | 0.0301 (10) | 0.0030 (8) | 0.0039 (7) | 0.0186 (9) |
Cl4F | 0.0512 (3) | 0.0373 (3) | 0.0361 (3) | 0.0072 (2) | 0.0118 (2) | 0.0265 (3) |
C5F | 0.0281 (10) | 0.0291 (11) | 0.0187 (9) | 0.0063 (8) | 0.0061 (7) | 0.0111 (9) |
C6F | 0.0211 (9) | 0.0221 (10) | 0.0268 (10) | 0.0030 (7) | 0.0033 (7) | 0.0111 (9) |
Cl6F | 0.0445 (3) | 0.0219 (3) | 0.0284 (3) | 0.0073 (2) | 0.0063 (2) | 0.0122 (2) |
N1A—C6A | 1.331 (2) | N1D—C6D | 1.327 (2) |
N1A—C2A | 1.340 (2) | N1D—C2D | 1.338 (2) |
C2A—N3A | 1.344 (2) | C2D—N3D | 1.352 (2) |
C2A—S21A | 1.7460 (19) | C2D—S21D | 1.744 (2) |
S21A—C22A | 1.794 (2) | S21D—C22D | 1.793 (2) |
C22A—H21A | 0.9800 | C22D—H21D | 0.9800 |
C22A—H22A | 0.9800 | C22D—H22D | 0.9800 |
C22A—H23A | 0.9800 | C22D—H23D | 0.9800 |
N3A—C4A | 1.321 (2) | N3D—C4D | 1.313 (3) |
C4A—C5A | 1.385 (3) | C4D—C5D | 1.386 (3) |
C4A—Cl4A | 1.7345 (18) | C4D—Cl4D | 1.7298 (18) |
C5A—C6A | 1.374 (3) | C5D—C6D | 1.378 (3) |
C5A—H5A | 0.9500 | C5D—H5D | 0.9500 |
C6A—Cl6A | 1.7315 (18) | C6D—Cl6D | 1.7274 (18) |
N1B—C6B | 1.330 (2) | N1E—C6E | 1.331 (2) |
N1B—C2B | 1.341 (2) | N1E—C2E | 1.340 (2) |
C2B—N3B | 1.347 (2) | C2E—N3E | 1.350 (2) |
C2B—S21B | 1.7472 (19) | C2E—S21E | 1.7447 (18) |
S21B—C22B | 1.798 (2) | S21E—C22E | 1.800 (2) |
C22B—H21B | 0.9800 | C22E—H21E | 0.9800 |
C22B—H22B | 0.9800 | C22E—H22E | 0.9800 |
C22B—H23B | 0.9800 | C22E—H23E | 0.9800 |
N3B—C4B | 1.316 (2) | N3E—C4E | 1.320 (2) |
C4B—C5B | 1.384 (3) | C4E—C5E | 1.386 (3) |
C4B—Cl4B | 1.7366 (19) | C4E—Cl4E | 1.733 (2) |
C5B—C6B | 1.376 (3) | C5E—C6E | 1.376 (3) |
C5B—H5B | 0.9500 | C5E—H5E | 0.9500 |
C6B—Cl6B | 1.7243 (18) | C6E—Cl6E | 1.7299 (18) |
N1C—C6C | 1.326 (2) | N1F—C6F | 1.326 (2) |
N1C—C2C | 1.346 (2) | N1F—C2F | 1.338 (2) |
C2C—N3C | 1.346 (2) | C2F—N3F | 1.354 (2) |
C2C—S21C | 1.7459 (19) | C2F—S21F | 1.7475 (18) |
S21C—C22C | 1.794 (2) | S21F—C22F | 1.796 (2) |
C22C—H21C | 0.9800 | C22F—H21F | 0.9800 |
C22C—H22C | 0.9800 | C22F—H22F | 0.9800 |
C22C—H23C | 0.9800 | C22F—H23F | 0.9800 |
N3C—C4C | 1.319 (2) | N3F—C4F | 1.314 (2) |
C4C—C5C | 1.385 (3) | C4F—C5F | 1.382 (3) |
C4C—Cl4C | 1.7304 (18) | C4F—Cl4F | 1.7340 (19) |
C5C—C6C | 1.373 (3) | C5F—C6F | 1.381 (3) |
C5C—H5C | 0.9500 | C5F—H5F | 0.9500 |
C6C—Cl6C | 1.7294 (19) | C6F—Cl6F | 1.7203 (19) |
C6A—N1A—C2A | 114.36 (16) | C6D—N1D—C2D | 114.73 (16) |
N1A—C2A—N3A | 126.83 (17) | N1D—C2D—N3D | 126.51 (18) |
N1A—C2A—S21A | 119.86 (14) | N1D—C2D—S21D | 119.88 (14) |
N3A—C2A—S21A | 113.31 (14) | N3D—C2D—S21D | 113.59 (14) |
C2A—S21A—C22A | 102.43 (9) | C2D—S21D—C22D | 101.92 (10) |
S21A—C22A—H21A | 109.5 | S21D—C22D—H21D | 109.5 |
S21A—C22A—H22A | 109.5 | S21D—C22D—H22D | 109.5 |
H21A—C22A—H22A | 109.5 | H21D—C22D—H22D | 109.5 |
S21A—C22A—H23A | 109.5 | S21D—C22D—H23D | 109.5 |
H21A—C22A—H23A | 109.5 | H21D—C22D—H23D | 109.5 |
H22A—C22A—H23A | 109.5 | H22D—C22D—H23D | 109.5 |
C4A—N3A—C2A | 114.93 (16) | C4D—N3D—C2D | 115.09 (16) |
N3A—C4A—C5A | 124.79 (17) | N3D—C4D—C5D | 124.76 (17) |
N3A—C4A—Cl4A | 116.54 (14) | N3D—C4D—Cl4D | 116.48 (14) |
C5A—C4A—Cl4A | 118.67 (15) | C5D—C4D—Cl4D | 118.76 (15) |
C6A—C5A—C4A | 113.77 (17) | C6D—C5D—C4D | 113.92 (18) |
C6A—C5A—H5A | 123.1 | C6D—C5D—H5D | 123.0 |
C4A—C5A—H5A | 123.1 | C4D—C5D—H5D | 123.0 |
N1A—C6A—C5A | 125.29 (17) | N1D—C6D—C5D | 124.98 (17) |
N1A—C6A—Cl6A | 115.95 (14) | N1D—C6D—Cl6D | 116.32 (14) |
C5A—C6A—Cl6A | 118.75 (15) | C5D—C6D—Cl6D | 118.70 (15) |
C6B—N1B—C2B | 114.52 (16) | C6E—N1E—C2E | 114.50 (16) |
N1B—C2B—N3B | 126.82 (17) | N1E—C2E—N3E | 126.64 (17) |
N1B—C2B—S21B | 119.81 (15) | N1E—C2E—S21E | 119.97 (15) |
N3B—C2B—S21B | 113.35 (13) | N3E—C2E—S21E | 113.38 (13) |
C2B—S21B—C22B | 102.40 (9) | C2E—S21E—C22E | 102.32 (9) |
S21B—C22B—H21B | 109.5 | S21E—C22E—H21E | 109.5 |
S21B—C22B—H22B | 109.5 | S21E—C22E—H22E | 109.5 |
H21B—C22B—H22B | 109.5 | H21E—C22E—H22E | 109.5 |
S21B—C22B—H23B | 109.5 | S21E—C22E—H23E | 109.5 |
H21B—C22B—H23B | 109.5 | H21E—C22E—H23E | 109.5 |
H22B—C22B—H23B | 109.5 | H22E—C22E—H23E | 109.5 |
C4B—N3B—C2B | 114.70 (16) | C4E—N3E—C2E | 114.97 (16) |
N3B—C4B—C5B | 125.12 (18) | N3E—C4E—C5E | 124.80 (18) |
N3B—C4B—Cl4B | 116.42 (14) | N3E—C4E—Cl4E | 116.45 (14) |
C5B—C4B—Cl4B | 118.46 (15) | C5E—C4E—Cl4E | 118.75 (15) |
C6B—C5B—C4B | 113.88 (17) | C6E—C5E—C4E | 113.80 (17) |
C6B—C5B—H5B | 123.1 | C6E—C5E—H5E | 123.1 |
C4B—C5B—H5B | 123.1 | C4E—C5E—H5E | 123.1 |
N1B—C6B—C5B | 124.92 (17) | N1E—C6E—C5E | 125.27 (17) |
N1B—C6B—Cl6B | 116.14 (14) | N1E—C6E—Cl6E | 116.18 (14) |
C5B—C6B—Cl6B | 118.94 (14) | C5E—C6E—Cl6E | 118.56 (14) |
C6C—N1C—C2C | 114.44 (16) | C6F—N1F—C2F | 114.86 (16) |
N3C—C2C—N1C | 126.68 (17) | N1F—C2F—N3F | 126.53 (17) |
N3C—C2C—S21C | 113.48 (14) | N1F—C2F—S21F | 120.05 (14) |
N1C—C2C—S21C | 119.83 (14) | N3F—C2F—S21F | 113.40 (14) |
C2C—S21C—C22C | 102.01 (10) | C2F—S21F—C22F | 102.17 (10) |
S21C—C22C—H21C | 109.5 | S21F—C22F—H21F | 109.5 |
S21C—C22C—H22C | 109.5 | S21F—C22F—H22F | 109.5 |
H21C—C22C—H22C | 109.5 | H21F—C22F—H22F | 109.5 |
S21C—C22C—H23C | 109.5 | S21F—C22F—H23F | 109.5 |
H21C—C22C—H23C | 109.5 | H21F—C22F—H23F | 109.5 |
H22C—C22C—H23C | 109.5 | H22F—C22F—H23F | 109.5 |
C4C—N3C—C2C | 114.80 (16) | C4F—N3F—C2F | 114.87 (16) |
N3C—C4C—C5C | 124.86 (17) | N3F—C4F—C5F | 124.90 (17) |
N3C—C4C—Cl4C | 116.32 (14) | N3F—C4F—Cl4F | 116.34 (15) |
C5C—C4C—Cl4C | 118.82 (14) | C5F—C4F—Cl4F | 118.76 (14) |
C6C—C5C—C4C | 113.92 (17) | C6F—C5F—C4F | 114.14 (16) |
C6C—C5C—H5C | 123.0 | C6F—C5F—H5F | 122.9 |
C4C—C5C—H5C | 123.0 | C4F—C5F—H5F | 122.9 |
N1C—C6C—C5C | 125.24 (18) | N1F—C6F—C5F | 124.67 (17) |
N1C—C6C—Cl6C | 115.95 (14) | N1F—C6F—Cl6F | 116.37 (14) |
C5C—C6C—Cl6C | 118.80 (14) | C5F—C6F—Cl6F | 118.95 (14) |
C6A—N1A—C2A—N3A | 0.6 (2) | C6D—N1D—C2D—N3D | 1.7 (2) |
C6A—N1A—C2A—S21A | −179.88 (12) | C6D—N1D—C2D—S21D | −176.41 (12) |
N1A—C2A—S21A—C22A | −2.21 (16) | N1D—C2D—S21D—C22D | −1.92 (16) |
N3A—C2A—S21A—C22A | 177.34 (13) | N3D—C2D—S21D—C22D | 179.71 (13) |
N1A—C2A—N3A—C4A | 0.7 (3) | N1D—C2D—N3D—C4D | −0.8 (3) |
S21A—C2A—N3A—C4A | −178.78 (13) | S21D—C2D—N3D—C4D | 177.47 (12) |
C2A—N3A—C4A—C5A | −2.0 (3) | C2D—N3D—C4D—C5D | −0.6 (3) |
C2A—N3A—C4A—Cl4A | 178.22 (12) | C2D—N3D—C4D—Cl4D | −179.73 (12) |
N3A—C4A—C5A—C6A | 1.8 (3) | N3D—C4D—C5D—C6D | 0.8 (3) |
Cl4A—C4A—C5A—C6A | −178.45 (13) | Cl4D—C4D—C5D—C6D | 179.94 (13) |
C2A—N1A—C6A—C5A | −0.9 (3) | C2D—N1D—C6D—C5D | −1.4 (3) |
C2A—N1A—C6A—Cl6A | −179.95 (12) | C2D—N1D—C6D—Cl6D | 177.94 (12) |
C4A—C5A—C6A—N1A | −0.2 (3) | C4D—C5D—C6D—N1D | 0.3 (3) |
C4A—C5A—C6A—Cl6A | 178.83 (13) | C4D—C5D—C6D—Cl6D | −179.09 (12) |
C6B—N1B—C2B—N3B | 2.0 (3) | C6E—N1E—C2E—N3E | −0.3 (3) |
C6B—N1B—C2B—S21B | −176.84 (12) | C6E—N1E—C2E—S21E | 179.64 (12) |
N1B—C2B—S21B—C22B | 0.11 (16) | N1E—C2E—S21E—C22E | 2.69 (16) |
N3B—C2B—S21B—C22B | −178.90 (13) | N3E—C2E—S21E—C22E | −177.34 (13) |
N1B—C2B—N3B—C4B | −2.2 (3) | N1E—C2E—N3E—C4E | −0.9 (3) |
S21B—C2B—N3B—C4B | 176.71 (12) | S21E—C2E—N3E—C4E | 179.18 (12) |
C2B—N3B—C4B—C5B | 0.7 (3) | C2E—N3E—C4E—C5E | 1.5 (3) |
C2B—N3B—C4B—Cl4B | −179.05 (12) | C2E—N3E—C4E—Cl4E | −178.59 (12) |
N3B—C4B—C5B—C6B | 0.8 (3) | N3E—C4E—C5E—C6E | −1.0 (3) |
Cl4B—C4B—C5B—C6B | −179.50 (13) | Cl4E—C4E—C5E—C6E | 179.14 (13) |
C2B—N1B—C6B—C5B | −0.3 (2) | C2E—N1E—C6E—C5E | 1.0 (2) |
C2B—N1B—C6B—Cl6B | 179.90 (12) | C2E—N1E—C6E—Cl6E | −179.40 (12) |
C4B—C5B—C6B—N1B | −1.0 (3) | C4E—C5E—C6E—N1E | −0.4 (3) |
C4B—C5B—C6B—Cl6B | 178.83 (13) | C4E—C5E—C6E—Cl6E | 180.00 (13) |
C6C—N1C—C2C—N3C | −2.6 (3) | C6F—N1F—C2F—N3F | −1.4 (3) |
C6C—N1C—C2C—S21C | 176.88 (12) | C6F—N1F—C2F—S21F | 177.31 (12) |
N3C—C2C—S21C—C22C | −177.40 (13) | N1F—C2F—S21F—C22F | −0.30 (17) |
N1C—C2C—S21C—C22C | 3.07 (16) | N3F—C2F—S21F—C22F | 178.56 (13) |
N1C—C2C—N3C—C4C | 1.7 (2) | N1F—C2F—N3F—C4F | 1.7 (3) |
S21C—C2C—N3C—C4C | −177.83 (12) | S21F—C2F—N3F—C4F | −177.09 (13) |
C2C—N3C—C4C—C5C | 0.7 (3) | C2F—N3F—C4F—C5F | −1.2 (3) |
C2C—N3C—C4C—Cl4C | −179.53 (12) | C2F—N3F—C4F—Cl4F | 178.19 (12) |
N3C—C4C—C5C—C6C | −1.8 (3) | N3F—C4F—C5F—C6F | 0.6 (3) |
Cl4C—C4C—C5C—C6C | 178.46 (13) | Cl4F—C4F—C5F—C6F | −178.82 (13) |
C2C—N1C—C6C—C5C | 1.3 (3) | C2F—N1F—C6F—C5F | 0.6 (3) |
C2C—N1C—C6C—Cl6C | −179.66 (12) | C2F—N1F—C6F—Cl6F | −178.35 (12) |
C4C—C5C—C6C—N1C | 0.7 (3) | C4F—C5F—C6F—N1F | −0.2 (3) |
C4C—C5C—C6C—Cl6C | −178.35 (13) | C4F—C5F—C6F—Cl6F | 178.69 (13) |