Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022483/ac2026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022483/ac2026Isup2.hkl |
CCDC reference: 614853
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.003 Å
- R factor = 0.040
- wR factor = 0.118
- Data-to-parameter ratio = 21.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT021_ALERT_1_C Ratio Unique / Expected Reflections too High ... 1.05 PLAT230_ALERT_2_C Hirshfeld Test Diff for C2 - C3 .. 5.01 su PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrystalClear (Rigaku/MSC, 2002); cell refinement: CrystalClear; data reduction: CrystalStructure (Rigaku/MSC, 2003); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Betteridge et al., 2003); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: CrystalStructure.
C20H16Cl4FN3O2S | F(000) = 1064.00 |
Mr = 523.24 | Dx = 1.552 Mg m−3 |
Monoclinic, P21/n | Melting point = 461–462 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.7107 Å |
a = 13.7862 (4) Å | Cell parameters from 18322 reflections |
b = 11.0663 (3) Å | θ = 2.3–30.0° |
c = 14.6971 (4) Å | µ = 0.65 mm−1 |
β = 93.277 (1)° | T = 294 K |
V = 2238.56 (11) Å3 | Prism, yellow |
Z = 4 | 0.50 × 0.40 × 0.20 mm |
Rigaku R-AXIS RAPID S diffractometer | 6335 reflections with F2 > 2σ(F2) |
Detector resolution: 10.00 pixels mm-1 | Rint = 0.035 |
ω scans | θmax = 30.1° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −19→19 |
Tmin = 0.682, Tmax = 0.878 | k = −15→15 |
131970 measured reflections | l = −20→20 |
6892 independent reflections |
Refinement on F | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.040 | Chebychev polynomial with 3 parameters (Carruthers & Watkin, 1979) 5.3958 -5.3010 2.8963 |
wR(F2) = 0.118 | (Δ/σ)max = 0.006 |
S = 1.09 | Δρmax = 0.93 e Å−3 |
6335 reflections | Δρmin = −0.56 e Å−3 |
296 parameters |
Geometry. Least Squares Planes ————– Plane number 1 ————— Atoms Defining Plane Distance e.s.d. C1 [1;0;0;0] 0.1333 0.0008 C2 [1;0;0;0] -0.2659 0.0015 C3 [1;0;0;0] 0.2006 0.0012 C4 [1;0;0;0] -0.0809 0.0005 Additional Atoms Distance e.s.d. Mean deviation from plane is 0.1702 angstrom Chi-squared: 29463.053 ————– Plane number 2 ————— Atoms Defining Plane Distance e.s.d. C5 [1;0;0;0] -0.0209 0.0014 C6 [1;0;0;0] 0.0198 0.0015 C7 [1;0;0;0] -0.0039 0.0017 C8 [1;0;0;0] -0.0130 0.0018 C9 [1;0;0;0] 0.0101 0.0021 C10 [1;0;0;0] 0.0144 0.0019 Additional Atoms Distance e.s.d. Mean deviation from plane is 0.0137 angstrom Chi-squared: 217.503 ————– Plane number 3 ————— Atoms Defining Plane Distance e.s.d. C11 [1;0;0;0] 0.0119 0.0012 C12 [1;0;0;0] -0.0109 0.0011 C13 [1;0;0;0] 0.0088 0.0009 C14 [1;0;0;0] -0.0094 0.0010 Additional Atoms Distance e.s.d. Mean deviation from plane is 0.0103 angstrom Chi-squared: 92.158 ————– Plane number 4 ————— Atoms Defining Plane Distance e.s.d. C15 [1;0;0;0] -0.0151 0.0014 C16 [1;0;0;0] 0.0153 0.0018 C17 [1;0;0;0] 0.0025 0.0020 C18 [1;0;0;0] -0.0150 0.0018 C19 [1;0;0;0] 0.0068 0.0017 C20 [1;0;0;0] 0.0074 0.0014 Additional Atoms Distance e.s.d. Mean deviation from plane is 0.0103 angstrom Chi-squared: 141.555 Dihedral angles between least-squares planes ——————————————– plane plane angle e.s.d. 1 2 130.281 0.099 1 3 64.749 0.107 1 4 96.752 0.087 2 3 164.116 0.091 2 4 132.281 0.083 3 4 35.133 0.077 |
Refinement. Refinement using reflections with F2 > 3.0 σ(F2). The weighted R-factor(wR), goodness of fit (S) and R-factor (gt) are based on F, with F set to zero for negative F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
S1 | 0.17363 (4) | 0.15888 (6) | 0.54893 (4) | 0.0499 (2) | |
Cl1 | 0.34677 (5) | −0.13614 (6) | 0.55203 (5) | 0.0724 (2) | |
Cl2 | 0.32734 (7) | −0.14662 (7) | 0.74592 (7) | 0.0916 (3) | |
Cl3 | 0.35492 (6) | 0.12678 (6) | 0.76283 (4) | 0.0770 (2) | |
Cl4 | −0.06475 (6) | −0.06201 (8) | 0.21365 (5) | 0.0922 (3) | |
O2 | 0.46752 (11) | 0.2868 (2) | 0.52823 (11) | 0.0584 (5) | |
F1 | 0.45386 (10) | 0.1146 (2) | 0.11612 (10) | 0.0746 (5) | |
N3 | 0.30676 (11) | 0.1681 (2) | 0.22944 (11) | 0.0393 (4) | |
N2 | 0.30860 (12) | 0.1877 (2) | 0.42395 (11) | 0.0403 (4) | |
N1 | 0.45701 (12) | 0.1974 (2) | 0.57726 (12) | 0.0464 (5) | |
O1 | 0.52383 (12) | 0.1604 (2) | 0.63042 (12) | 0.0689 (6) | |
C12 | 0.3628 (2) | 0.0846 (2) | 0.29051 (13) | 0.0435 (6) | |
C13 | 0.2205 (1) | 0.2117 (2) | 0.27370 (13) | 0.0398 (5) | |
C15 | 0.2858 (2) | 0.1186 (2) | 0.14085 (13) | 0.0398 (5) | |
C3 | 0.3652 (1) | 0.1384 (2) | 0.57742 (13) | 0.0398 (5) | |
C5 | 0.1042 (1) | 0.0928 (2) | 0.4558 (1) | 0.0429 (6) | |
C4 | 0.2925 (1) | 0.1630 (2) | 0.51078 (13) | 0.0395 (5) | |
C11 | 0.3948 (1) | 0.1449 (2) | 0.38037 (13) | 0.0452 (6) | |
C20 | 0.1919 (2) | 0.0984 (2) | 0.10379 (13) | 0.0428 (6) | |
C6 | 0.1281 (2) | −0.0183 (2) | 0.4226 (1) | 0.0484 (6) | |
C14 | 0.2501 (2) | 0.2702 (2) | 0.36472 (13) | 0.0415 (5) | |
C8 | −0.0024 (2) | −0.0046 (2) | 0.3102 (2) | 0.0550 (7) | |
C1 | 0.3442 (2) | −0.0584 (2) | 0.6513 (2) | 0.0510 (7) | |
C2 | 0.3546 (2) | 0.0596 (2) | 0.6554 (1) | 0.0465 (6) | |
C7 | 0.0758 (2) | −0.0677 (2) | 0.3473 (2) | 0.0526 (7) | |
C16 | 0.3611 (2) | 0.0901 (2) | 0.0856 (1) | 0.0503 (6) | |
C19 | 0.1754 (2) | 0.0475 (2) | 0.0168 (1) | 0.0521 (7) | |
C18 | 0.2519 (2) | 0.0168 (2) | −0.0334 (2) | 0.0566 (7) | |
C17 | 0.3459 (2) | 0.0391 (2) | 0.0005 (2) | 0.0606 (8) | |
C10 | 0.0233 (2) | 0.1530 (2) | 0.4193 (2) | 0.0587 (7) | |
C9 | −0.0300 (2) | 0.1028 (2) | 0.3449 (2) | 0.0661 (8) | |
H(1) | 0.1822 | −0.0607 | 0.4498 | 0.0577* | |
H(2) | 0.0911 | −0.1446 | 0.3234 | 0.0631* | |
H(3) | −0.0853 | 0.1436 | 0.3185 | 0.0781* | |
H(4) | 0.0041 | 0.2276 | 0.4447 | 0.0701* | |
H(5) | 0.4358 | 0.2114 | 0.36852 | 0.0543* | |
H(6) | 0.4293 | 0.0887 | 0.41886 | 0.0542* | |
H(7) | 0.3232 | 0.0171 | 0.30329 | 0.0521* | |
H(8) | 0.4182 | 0.0580 | 0.26070 | 0.0524* | |
H(9) | 0.1875 | 0.2690 | 0.23497 | 0.0475* | |
H(10) | 0.1787 | 0.1454 | 0.28359 | 0.0474* | |
H(11) | 0.1931 | 0.2910 | 0.39466 | 0.0497* | |
H(12) | 0.2865 | 0.3412 | 0.35414 | 0.0496* | |
H(13) | 0.3994 | 0.0181 | −0.0344 | 0.0730* | |
H(14) | 0.2403 | −0.0192 | −0.0916 | 0.0676* | |
H(15) | 0.1107 | 0.0340 | −0.0068 | 0.0621* | |
H(16) | 0.1379 | 0.1198 | 0.13782 | 0.0512* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0422 (3) | 0.0651 (4) | 0.0428 (3) | −0.0047 (3) | 0.0054 (2) | −0.0109 (3) |
Cl1 | 0.0669 (4) | 0.0597 (4) | 0.0883 (5) | 0.0105 (3) | −0.0157 (4) | −0.0288 (4) |
Cl2 | 0.1055 (6) | 0.0631 (4) | 0.1085 (6) | 0.0040 (4) | 0.0250 (5) | 0.0319 (4) |
Cl3 | 0.1237 (6) | 0.0659 (4) | 0.0417 (3) | 0.0014 (4) | 0.0077 (4) | −0.0070 (3) |
Cl4 | 0.0971 (6) | 0.0958 (6) | 0.0783 (5) | −0.0231 (5) | −0.0405 (4) | −0.0006 (4) |
O2 | 0.0569 (10) | 0.0575 (10) | 0.0597 (10) | −0.0178 (8) | −0.0070 (8) | 0.0050 (8) |
F1 | 0.0457 (7) | 0.120 (1) | 0.0593 (9) | −0.0070 (8) | 0.0108 (6) | −0.0086 (9) |
N3 | 0.0394 (8) | 0.0455 (10) | 0.0330 (8) | 0.0009 (8) | 0.0010 (7) | 0.0009 (7) |
N2 | 0.0379 (8) | 0.0449 (10) | 0.0380 (9) | 0.0008 (7) | 0.0007 (7) | −0.0021 (7) |
N1 | 0.0438 (10) | 0.0502 (11) | 0.0442 (10) | −0.0082 (8) | −0.0065 (8) | 0.0013 (8) |
O1 | 0.0512 (9) | 0.0842 (13) | 0.0689 (11) | −0.0104 (9) | −0.0184 (8) | 0.0137 (10) |
C12 | 0.0408 (11) | 0.0543 (13) | 0.0355 (10) | 0.0084 (10) | 0.0022 (8) | 0.0020 (9) |
C13 | 0.0403 (10) | 0.0399 (11) | 0.0388 (10) | 0.0038 (9) | −0.0010 (8) | 0.0020 (9) |
C15 | 0.0476 (11) | 0.0402 (11) | 0.0314 (10) | 0.0019 (9) | −0.0002 (8) | 0.0031 (8) |
C3 | 0.0418 (10) | 0.0419 (11) | 0.0355 (10) | −0.0060 (9) | 0.0006 (8) | −0.0013 (9) |
C5 | 0.0372 (10) | 0.0469 (12) | 0.0444 (11) | −0.0039 (9) | −0.0001 (9) | 0.0003 (9) |
C4 | 0.0413 (10) | 0.0398 (11) | 0.0370 (10) | −0.0034 (9) | −0.0017 (8) | −0.0047 (8) |
C11 | 0.0366 (10) | 0.059 (1) | 0.0398 (10) | 0.0004 (10) | 0.0036 (8) | 0.0017 (10) |
C20 | 0.0440 (11) | 0.0501 (12) | 0.0342 (10) | 0.0054 (10) | 0.0018 (8) | 0.0024 (9) |
C6 | 0.0428 (12) | 0.0523 (13) | 0.0491 (12) | 0.0022 (10) | −0.0049 (9) | 0.0008 (10) |
C14 | 0.0483 (12) | 0.0357 (11) | 0.0403 (11) | 0.0006 (9) | 0.0010 (9) | −0.0019 (9) |
C8 | 0.0511 (13) | 0.059 (2) | 0.0527 (13) | −0.0116 (12) | −0.0132 (10) | 0.0035 (12) |
C1 | 0.0456 (12) | 0.0499 (13) | 0.058 (1) | 0.0012 (10) | 0.0042 (10) | 0.0004 (11) |
C2 | 0.0521 (13) | 0.0459 (12) | 0.0416 (11) | −0.0029 (10) | 0.0037 (9) | −0.0041 (10) |
C7 | 0.0537 (13) | 0.0465 (13) | 0.057 (1) | −0.0033 (11) | 0.0011 (11) | −0.0072 (11) |
C16 | 0.0423 (12) | 0.069 (2) | 0.0398 (11) | 0.0008 (11) | 0.0067 (9) | 0.0033 (11) |
C19 | 0.057 (1) | 0.058 (1) | 0.0398 (11) | 0.0051 (11) | −0.0068 (10) | 0.0005 (10) |
C18 | 0.067 (2) | 0.066 (2) | 0.0360 (11) | 0.0103 (13) | −0.0021 (10) | −0.0049 (11) |
C17 | 0.062 (2) | 0.080 (2) | 0.0410 (12) | 0.0128 (13) | 0.0118 (11) | 0.0024 (12) |
C10 | 0.0457 (12) | 0.052 (1) | 0.077 (2) | 0.0056 (11) | −0.0050 (11) | −0.0056 (12) |
C9 | 0.051 (1) | 0.064 (2) | 0.081 (2) | 0.0039 (12) | −0.0203 (13) | 0.004 (1) |
S1—C5 | 1.781 (2) | C3—C2 | 1.454 (3) |
S1—C4 | 1.763 (2) | C5—C6 | 1.370 (3) |
Cl1—C1 | 1.696 (2) | C5—C10 | 1.382 (3) |
Cl2—C1 | 1.726 (3) | C11—H(5) | 0.95 |
Cl3—C2 | 1.745 (2) | C11—H(6) | 0.95 |
Cl4—C8 | 1.737 (2) | C20—C19 | 1.403 (3) |
O2—N1 | 1.237 (2) | C20—H(16) | 0.95 |
F1—C16 | 1.358 (3) | C6—C7 | 1.397 (3) |
N3—C12 | 1.475 (3) | C6—H(1) | 0.95 |
N3—C13 | 1.470 (3) | C14—H(11) | 0.95 |
N3—C15 | 1.427 (2) | C14—H(12) | 0.95 |
N2—C4 | 1.336 (3) | C8—C7 | 1.371 (3) |
N2—C11 | 1.461 (3) | C8—C9 | 1.356 (4) |
N2—C14 | 1.470 (3) | C1—C2 | 1.314 (3) |
N1—O1 | 1.243 (2) | C7—H(2) | 0.95 |
N1—C3 | 1.424 (3) | C16—C17 | 1.378 (3) |
C12—C11 | 1.522 (3) | C19—C18 | 1.365 (3) |
C12—H(7) | 0.95 | C19—H(15) | 0.95 |
C12—H(8) | 0.95 | C18—C17 | 1.383 (3) |
C13—C14 | 1.520 (3) | C18—H(14) | 0.95 |
C13—H(9) | 0.95 | C17—H(13) | 0.95 |
C13—H(10) | 0.95 | C10—C9 | 1.397 (4) |
C15—C20 | 1.393 (3) | C10—H(4) | 0.95 |
C15—C16 | 1.390 (3) | C9—H(3) | 0.950 (4) |
C3—C4 | 1.387 (3) | ||
S1···N2 | 2.707 (2) | C7···H(1) | 2.043 (3) |
S1···C3 | 2.660 (2) | C7···H(3) | 3.236 (3) |
S1···C6 | 2.748 (2) | C7···H(10) | 2.933 (3) |
S1···C14 | 3.207 (2) | C16···N3 | 2.440 (3) |
S1···C2 | 3.072 (2) | C16···C12 | 3.010 (3) |
S1···C10 | 2.735 (2) | C16···C20 | 2.365 (3) |
S1···H(1) | 2.839 (2) | C16···C19 | 2.739 (3) |
S1···H(4) | 2.824 (2) | C16···C18 | 2.383 (3) |
S1···H(11) | 2.724 (2) | C16···H(2) | 3.277 (3) |
Cl1···Cl2 | 2.880 (1) | C16···H(4) | 3.565 (3) |
Cl1···C3 | 3.070 (2) | C16···H(7) | 3.369 (3) |
Cl1···C4 | 3.440 (2) | C16···H(8) | 2.671 (3) |
Cl1···C2 | 2.644 (2) | C16···H(11) | 3.409 (3) |
Cl1···H(1) | 2.777 (2) | C16···H(12) | 3.566 (3) |
Cl1···H(6) | 3.402 (2) | C16···H(13) | 2.032 (3) |
Cl2···Cl1 | 2.880 (1) | C16···H(14) | 3.245 (3) |
Cl2···Cl3 | 3.058 (1) | C16···H(16) | 3.230 (3) |
Cl2···Cl4 | 3.594 (1) | C19···S1 | 2.473 (2) |
Cl2···C2 | 2.679 (2) | C19···Cl1 | 2.473 (2) |
Cl3···Cl2 | 3.058 (1) | C19···Cl2 | 2.473 (3) |
Cl3···N1 | 3.236 (2) | C19···Cl3 | 2.473 (2) |
Cl3···O1 | 3.141 (2) | C19···Cl4 | 2.473 (2) |
Cl3···C3 | 2.740 (2) | C19···O2 | 3.535 (3) |
Cl3···C1 | 2.623 (2) | C19···O2 | 3.414 (3) |
Cl3···C9 | 3.565 (3) | C19···O2 | 2.473 (3) |
Cl3···H(3) | 2.780 (3) | C19···F1 | 2.473 (3) |
Cl4···S1 | 3.383 (1) | C19···N3 | 2.473 (3) |
Cl4···Cl1 | 3.383 (1) | C19···N2 | 2.473 (3) |
Cl4···Cl2 | 3.594 (1) | C19···N1 | 2.473 (3) |
Cl4···Cl2 | 3.383 (1) | C19···O1 | 2.473 (3) |
Cl4···Cl3 | 3.383 (1) | C19···C12 | 2.473 (3) |
Cl4···Cl4 | 3.383 (1) | C19···C13 | 2.473 (3) |
Cl4···O2 | 3.383 (2) | C19···C15 | 2.437 (3) |
Cl4···F1 | 3.383 (2) | C19···C15 | 2.473 (3) |
Cl4···N3 | 3.383 (2) | C19···C3 | 2.473 (3) |
Cl4···N2 | 3.383 (2) | C19···C5 | 2.473 (3) |
Cl4···N1 | 3.383 (2) | C19···C4 | 2.473 (3) |
Cl4···O1 | 3.383 (2) | C19···C11 | 2.473 (3) |
Cl4···C12 | 3.383 (2) | C19···C20 | 2.473 (3) |
Cl4···C13 | 3.383 (2) | C19···C6 | 2.473 (3) |
Cl4···C15 | 3.383 (2) | C19···C14 | 2.473 (3) |
Cl4···C3 | 3.383 (2) | C19···C8 | 2.473 (3) |
Cl4···C5 | 3.383 (2) | C19···C1 | 2.473 (3) |
Cl4···C4 | 3.383 (2) | C19···C2 | 2.473 (3) |
Cl4···C11 | 3.383 (2) | C19···C7 | 2.473 (3) |
Cl4···C20 | 3.383 (2) | C19···C16 | 2.739 (3) |
Cl4···C6 | 3.383 (2) | C19···C16 | 2.473 (3) |
Cl4···C14 | 3.383 (2) | C19···C19 | 2.473 (3) |
Cl4···C8 | 3.383 (2) | C19···C18 | 2.473 (3) |
Cl4···C1 | 3.383 (2) | C19···C17 | 2.379 (3) |
Cl4···C2 | 3.383 (2) | C19···C17 | 2.473 (3) |
Cl4···C7 | 2.680 (2) | C19···C10 | 2.473 (3) |
Cl4···C7 | 3.383 (2) | C19···C9 | 2.473 (3) |
Cl4···C16 | 3.383 (2) | C19···H(1) | 2.473 (3) |
Cl4···C19 | 3.383 (2) | C19···H(2) | 2.473 (3) |
Cl4···C18 | 3.383 (2) | C19···H(3) | 2.473 (3) |
Cl4···C17 | 3.383 (2) | C19···H(4) | 2.473 (3) |
Cl4···C10 | 3.383 (3) | C19···H(5) | 2.473 (3) |
Cl4···C9 | 2.678 (3) | C19···H(6) | 2.473 (3) |
Cl4···C9 | 3.383 (3) | C19···H(7) | 2.473 (3) |
Cl4···H(1) | 3.383 (2) | C19···H(8) | 2.473 (3) |
Cl4···H(2) | 2.768 (2) | C19···H(9) | 2.473 (3) |
Cl4···H(2) | 3.383 (2) | C19···H(10) | 2.473 (3) |
Cl4···H(3) | 2.772 (3) | C19···H(11) | 3.573 (3) |
Cl4···H(3) | 3.383 (3) | C19···H(11) | 2.473 (3) |
Cl4···H(4) | 3.383 (3) | C19···H(12) | 2.996 (3) |
Cl4···H(5) | 3.339 (2) | C19···H(12) | 2.473 (3) |
Cl4···H(5) | 3.383 (2) | C19···H(13) | 3.237 (3) |
Cl4···H(6) | 3.383 (2) | C19···H(13) | 2.473 (3) |
Cl4···H(7) | 3.383 (2) | C19···H(14) | 2.013 (3) |
Cl4···H(8) | 3.383 (2) | C19···H(14) | 2.473 (3) |
Cl4···H(9) | 3.383 (2) | C19···H(15) | 2.473 (3) |
Cl4···H(10) | 3.383 (2) | C19···H(16) | 2.043 (3) |
Cl4···H(11) | 3.383 (2) | C19···H(16) | 2.473 (3) |
Cl4···H(12) | 3.383 (2) | C18···S1 | 3.540 (3) |
Cl4···H(13) | 3.383 (2) | C18···Cl1 | 3.540 (3) |
Cl4···H(14) | 3.063 (2) | C18···Cl2 | 3.540 (3) |
Cl4···H(14) | 3.383 (2) | C18···Cl3 | 3.599 (2) |
Cl4···H(15) | 3.085 (2) | C18···Cl3 | 3.540 (3) |
Cl4···H(15) | 3.383 (2) | C18···Cl4 | 3.540 (3) |
Cl4···H(16) | 3.383 (2) | C18···O2 | 3.540 (3) |
O2···N2 | 2.823 (2) | C18···F1 | 3.540 (3) |
O2···O1 | 2.164 (2) | C18···N3 | 3.540 (3) |
O2···C3 | 2.307 (3) | C18···N2 | 3.540 (3) |
O2···C4 | 2.774 (2) | C18···N1 | 3.540 (3) |
O2···C11 | 2.818 (3) | C18···O1 | 3.540 (3) |
O2···C20 | 3.467 (3) | C18···C12 | 3.540 (3) |
O2···C2 | 3.545 (3) | C18···C13 | 3.540 (3) |
O2···C19 | 3.535 (3) | C18···C15 | 2.811 (3) |
O2···C19 | 3.414 (3) | C18···C15 | 3.540 (3) |
O2···H(5) | 2.506 (3) | C18···C3 | 3.540 (3) |
O2···H(6) | 2.751 (3) | C18···C5 | 3.540 (3) |
O2···H(12) | 3.523 (2) | C18···C4 | 3.540 (3) |
O2···H(15) | 2.951 (3) | C18···C11 | 3.540 (3) |
O2···H(15) | 2.865 (3) | C18···C20 | 2.399 (3) |
O2···H(16) | 2.958 (3) | C18···C20 | 3.540 (3) |
F1···N3 | 2.761 (2) | C18···C6 | 3.540 (3) |
F1···C12 | 2.937 (2) | C18···C14 | 3.540 (3) |
F1···C15 | 2.367 (3) | C18···C8 | 3.540 (3) |
F1···C7 | 3.584 (3) | C18···C1 | 3.540 (3) |
F1···C17 | 2.347 (3) | C18···C2 | 3.540 (3) |
F1···H(2) | 2.888 (3) | C18···C7 | 3.540 (3) |
F1···H(4) | 3.174 (3) | C18···C16 | 2.383 (3) |
F1···H(7) | 3.541 (3) | C18···C16 | 3.540 (3) |
F1···H(8) | 2.295 (2) | C18···C19 | 3.540 (3) |
F1···H(13) | 2.531 (3) | C18···C18 | 3.540 (4) |
F1···H(13) | 2.823 (3) | C18···C17 | 3.540 (4) |
N3···F1 | 2.761 (2) | C18···C10 | 3.540 (3) |
N3···N2 | 2.866 (2) | C18···C9 | 3.540 (4) |
N3···C11 | 2.480 (2) | C18···H(1) | 3.540 (3) |
N3···C20 | 2.486 (2) | C18···H(2) | 3.540 (3) |
N3···C14 | 2.453 (3) | C18···H(3) | 3.540 (4) |
N3···C7 | 3.558 (3) | C18···H(4) | 3.540 (3) |
N3···C16 | 2.440 (3) | C18···H(5) | 3.540 (3) |
N3···H(2) | 2.647 (3) | C18···H(6) | 3.540 (3) |
N3···H(5) | 2.675 (2) | C18···H(7) | 3.540 (3) |
N3···H(6) | 3.292 (2) | C18···H(8) | 3.540 (3) |
N3···H(7) | 1.998 (3) | C18···H(9) | 3.540 (3) |
N3···H(8) | 1.994 (3) | C18···H(10) | 3.540 (3) |
N3···H(9) | 1.993 (3) | C18···H(11) | 3.286 (3) |
N3···H(10) | 1.994 (3) | C18···H(11) | 3.540 (3) |
N3···H(11) | 3.262 (3) | C18···H(12) | 3.340 (3) |
N3···H(12) | 2.677 (3) | C18···H(12) | 3.540 (3) |
N3···H(16) | 2.676 (2) | C18···H(13) | 2.034 (4) |
N2···S1 | 2.707 (2) | C18···H(13) | 3.540 (4) |
N2···O2 | 2.823 (2) | C18···H(14) | 3.540 (4) |
N2···N3 | 2.866 (2) | C18···H(15) | 2.017 (3) |
N2···N1 | 2.958 (2) | C18···H(15) | 3.540 (3) |
N2···C12 | 2.423 (3) | C18···H(16) | 3.248 (3) |
N2···C13 | 2.473 (2) | C18···H(16) | 3.540 (3) |
N2···C3 | 2.407 (2) | C17···F1 | 2.347 (3) |
N2···C5 | 3.068 (3) | C17···C15 | 2.432 (3) |
N2···C6 | 3.373 (3) | C17···C20 | 2.760 (3) |
N2···H(1) | 3.288 (3) | C17···C19 | 2.379 (3) |
N2···H(5) | 1.992 (3) | C17···H(4) | 3.507 (4) |
N2···H(6) | 1.997 (3) | C17···H(11) | 3.209 (3) |
N2···H(7) | 2.606 (3) | C17···H(13) | 3.574 (3) |
N2···H(8) | 3.243 (3) | C17···H(14) | 2.036 (3) |
N2···H(9) | 3.283 (2) | C17···H(15) | 3.239 (3) |
N2···H(10) | 2.694 (2) | C10···S1 | 2.735 (2) |
N2···H(11) | 1.987 (3) | C10···C6 | 2.382 (3) |
N2···H(12) | 1.999 (3) | C10···C14 | 3.520 (3) |
N1···Cl3 | 3.236 (2) | C10···C8 | 2.381 (3) |
N1···N2 | 2.958 (2) | C10···C7 | 2.773 (3) |
N1···C4 | 2.447 (3) | C10···H(1) | 3.238 (3) |
N1···C11 | 3.027 (3) | C10···H(3) | 2.048 (3) |
N1···C1 | 3.437 (3) | C10···H(10) | 3.011 (3) |
N1···C2 | 2.413 (3) | C10···H(11) | 2.837 (3) |
N1···H(5) | 3.069 (3) | C9···Cl3 | 3.565 (3) |
N1···H(6) | 2.629 (3) | C9···Cl4 | 2.678 (3) |
N1···H(16) | 3.294 (3) | C9···C5 | 2.398 (3) |
O1···Cl3 | 3.141 (2) | C9···C6 | 2.751 (3) |
O1···O2 | 2.164 (2) | C9···C7 | 2.384 (4) |
O1···C3 | 2.292 (3) | C9···H(2) | 3.232 (4) |
O1···C4 | 3.553 (2) | C9···H(4) | 2.050 (4) |
O1···C20 | 3.571 (3) | C9···H(10) | 3.099 (3) |
O1···C1 | 3.489 (3) | H(1)···S1 | 2.839 (2) |
O1···C2 | 2.630 (3) | H(1)···Cl1 | 2.777 (2) |
O1···H(6) | 3.396 (3) | H(1)···N2 | 3.288 (3) |
O1···H(9) | 2.769 (3) | H(1)···C5 | 2.015 (3) |
O1···H(16) | 2.896 (3) | H(1)···C4 | 3.014 (3) |
C12···F1 | 2.937 (2) | H(1)···C8 | 3.237 (3) |
C12···N2 | 2.423 (3) | H(1)···C7 | 2.043 (3) |
C12···C13 | 2.415 (3) | H(1)···C10 | 3.238 (3) |
C12···C15 | 2.416 (3) | H(2)···Cl4 | 2.768 (2) |
C12···C4 | 3.539 (3) | H(2)···F1 | 2.888 (3) |
C12···C20 | 3.516 (3) | H(2)···N3 | 2.647 (3) |
C12···C14 | 2.831 (3) | H(2)···C12 | 3.507 (3) |
C12···C16 | 3.010 (3) | H(2)···C13 | 3.425 (3) |
C12···H(2) | 3.507 (3) | H(2)···C15 | 3.150 (3) |
C12···H(5) | 2.041 (3) | H(2)···C5 | 3.269 (3) |
C12···H(6) | 2.051 (3) | H(2)···C6 | 2.063 (3) |
C12···H(9) | 3.231 (3) | H(2)···C8 | 2.019 (3) |
C12···H(9) | 3.577 (3) | H(2)···C16 | 3.277 (3) |
C12···H(10) | 2.621 (3) | H(2)···C9 | 3.232 (4) |
C12···H(12) | 3.186 (3) | H(3)···Cl3 | 2.780 (3) |
C13···N2 | 2.473 (2) | H(3)···Cl4 | 2.772 (3) |
C13···C12 | 2.415 (3) | H(3)···C5 | 3.258 (3) |
C13···C15 | 2.426 (3) | H(3)···C8 | 2.007 (4) |
C13···C5 | 3.459 (3) | H(3)···C7 | 3.236 (3) |
C13···C11 | 2.889 (3) | H(3)···C10 | 2.048 (3) |
C13···C20 | 2.802 (3) | H(4)···S1 | 2.824 (2) |
C13···H(2) | 3.425 (3) | H(4)···F1 | 3.174 (3) |
C13···H(5) | 3.206 (3) | H(4)···C5 | 2.032 (3) |
C13···H(7) | 2.600 (3) | H(4)···C6 | 3.240 (3) |
C13···H(8) | 3.229 (3) | H(4)···C8 | 3.239 (3) |
C13···H(11) | 2.037 (3) | H(4)···C16 | 3.565 (3) |
C13···H(12) | 2.038 (3) | H(4)···C17 | 3.507 (4) |
C13···H(16) | 2.462 (3) | H(4)···C9 | 2.050 (4) |
C15···F1 | 2.367 (3) | H(5)···Cl4 | 3.339 (2) |
C15···C12 | 2.416 (3) | H(5)···O2 | 2.506 (3) |
C15···C13 | 2.426 (3) | H(5)···N3 | 2.675 (2) |
C15···C19 | 2.437 (3) | H(5)···N2 | 1.992 (3) |
C15···C18 | 2.811 (3) | H(5)···N1 | 3.069 (3) |
C15···C17 | 2.432 (3) | H(5)···C12 | 2.041 (3) |
C15···H(2) | 3.150 (3) | H(5)···C13 | 3.206 (3) |
C15···H(7) | 2.662 (3) | H(5)···C3 | 3.371 (3) |
C15···H(8) | 2.553 (3) | H(5)···C4 | 3.005 (3) |
C15···H(9) | 2.595 (3) | H(5)···C14 | 2.639 (3) |
C15···H(10) | 2.650 (3) | H(6)···Cl1 | 3.402 (2) |
C15···H(12) | 3.229 (3) | H(6)···O2 | 2.751 (3) |
C15···H(13) | 3.284 (3) | H(6)···N3 | 3.292 (2) |
C15···H(15) | 3.288 (3) | H(6)···N2 | 1.997 (3) |
C15···H(16) | 2.036 (3) | H(6)···N1 | 2.629 (3) |
C3···S1 | 2.660 (2) | H(6)···O1 | 3.396 (3) |
C3···Cl1 | 3.070 (2) | H(6)···C12 | 2.051 (3) |
C3···Cl3 | 2.740 (2) | H(6)···C3 | 2.598 (3) |
C3···O2 | 2.307 (3) | H(6)···C4 | 2.520 (3) |
C3···N2 | 2.407 (2) | H(6)···C14 | 3.248 (3) |
C3···O1 | 2.292 (3) | H(7)···F1 | 3.541 (3) |
C3···C11 | 2.948 (3) | H(7)···N3 | 1.998 (3) |
C3···C1 | 2.458 (3) | H(7)···N2 | 2.606 (3) |
C3···H(5) | 3.371 (3) | H(7)···C13 | 2.600 (3) |
C3···H(6) | 2.598 (3) | H(7)···C15 | 2.662 (3) |
C5···N2 | 3.068 (3) | H(7)···C4 | 3.497 (3) |
C5···C13 | 3.459 (3) | H(7)···C11 | 2.032 (3) |
C5···C4 | 2.785 (3) | H(7)···C20 | 3.475 (3) |
C5···C14 | 3.162 (3) | H(7)···C6 | 3.316 (3) |
C5···C8 | 2.746 (3) | H(7)···C14 | 3.127 (3) |
C5···C7 | 2.404 (3) | H(7)···C16 | 3.369 (3) |
C5···C9 | 2.398 (3) | H(8)···F1 | 2.295 (2) |
C5···H(1) | 2.015 (3) | H(8)···N3 | 1.994 (3) |
C5···H(2) | 3.269 (3) | H(8)···N2 | 3.243 (3) |
C5···H(3) | 3.258 (3) | H(8)···C13 | 3.229 (3) |
C5···H(4) | 2.032 (3) | H(8)···C15 | 2.553 (3) |
C5···H(10) | 2.846 (3) | H(8)···C11 | 2.047 (3) |
C5···H(11) | 2.693 (3) | H(8)···C16 | 2.671 (3) |
C4···Cl1 | 3.440 (2) | H(9)···N3 | 1.993 (3) |
C4···O2 | 2.774 (2) | H(9)···N2 | 3.283 (2) |
C4···N1 | 2.447 (3) | H(9)···O1 | 2.769 (3) |
C4···O1 | 3.553 (2) | H(9)···C12 | 3.231 (3) |
C4···C12 | 3.539 (3) | H(9)···C12 | 3.577 (3) |
C4···C5 | 2.785 (3) | H(9)···C15 | 2.595 (3) |
C4···C11 | 2.452 (3) | H(9)···C20 | 2.701 (3) |
C4···C6 | 3.240 (3) | H(9)···C14 | 2.048 (3) |
C4···C14 | 2.493 (3) | H(10)···N3 | 1.994 (3) |
C4···C1 | 3.257 (3) | H(10)···N2 | 2.694 (2) |
C4···C2 | 2.520 (3) | H(10)···C12 | 2.621 (3) |
C4···H(1) | 3.014 (3) | H(10)···C15 | 2.650 (3) |
C4···H(5) | 3.005 (3) | H(10)···C5 | 2.846 (3) |
C4···H(6) | 2.520 (3) | H(10)···C11 | 3.227 (3) |
C4···H(7) | 3.497 (3) | H(10)···C20 | 2.709 (3) |
C4···H(11) | 2.556 (3) | H(10)···C6 | 2.846 (3) |
C4···H(12) | 3.029 (3) | H(10)···C14 | 2.041 (3) |
C11···O2 | 2.818 (3) | H(10)···C8 | 3.041 (3) |
C11···N3 | 2.480 (2) | H(10)···C7 | 2.933 (3) |
C11···N1 | 3.027 (3) | H(10)···C10 | 3.011 (3) |
C11···C13 | 2.889 (3) | H(10)···C9 | 3.099 (3) |
C11···C3 | 2.948 (3) | H(11)···S1 | 2.724 (2) |
C11···C4 | 2.452 (3) | H(11)···N3 | 3.262 (3) |
C11···C14 | 2.430 (3) | H(11)···N2 | 1.987 (3) |
C11···H(7) | 2.032 (3) | H(11)···C13 | 2.037 (3) |
C11···H(8) | 2.047 (3) | H(11)···C5 | 2.693 (3) |
C11···H(10) | 3.227 (3) | H(11)···C4 | 2.556 (3) |
C11···H(11) | 3.233 (3) | H(11)···C11 | 3.233 (3) |
C11···H(12) | 2.652 (3) | H(11)···C6 | 3.568 (3) |
C20···S1 | 3.170 (2) | H(11)···C16 | 3.409 (3) |
C20···Cl1 | 3.170 (2) | H(11)···C19 | 3.573 (3) |
C20···Cl2 | 3.170 (2) | H(11)···C18 | 3.286 (3) |
C20···Cl3 | 3.170 (2) | H(11)···C17 | 3.209 (3) |
C20···Cl4 | 3.170 (2) | H(11)···C10 | 2.837 (3) |
C20···O2 | 3.467 (3) | H(12)···O2 | 3.523 (2) |
C20···O2 | 3.170 (3) | H(12)···N3 | 2.677 (3) |
C20···F1 | 3.170 (2) | H(12)···N2 | 1.999 (3) |
C20···N3 | 2.486 (2) | H(12)···C12 | 3.186 (3) |
C20···N3 | 3.170 (3) | H(12)···C13 | 2.038 (3) |
C20···N2 | 3.170 (3) | H(12)···C15 | 3.229 (3) |
C20···N1 | 3.170 (3) | H(12)···C4 | 3.029 (3) |
C20···O1 | 3.571 (3) | H(12)···C11 | 2.652 (3) |
C20···O1 | 3.170 (3) | H(12)···C20 | 2.924 (3) |
C20···C12 | 3.516 (3) | H(12)···C16 | 3.566 (3) |
C20···C12 | 3.170 (3) | H(12)···C19 | 2.996 (3) |
C20···C13 | 2.802 (3) | H(12)···C18 | 3.340 (3) |
C20···C13 | 3.170 (3) | H(13)···Cl3 | 3.240 (2) |
C20···C15 | 3.170 (3) | H(13)···F1 | 2.531 (3) |
C20···C3 | 3.170 (3) | H(13)···F1 | 2.823 (3) |
C20···C5 | 3.170 (3) | H(13)···C15 | 3.284 (3) |
C20···C4 | 3.170 (3) | H(13)···C16 | 2.032 (3) |
C20···C11 | 3.170 (3) | H(13)···C19 | 3.237 (3) |
C20···C20 | 3.170 (3) | H(13)···C18 | 2.034 (4) |
C20···C6 | 3.170 (3) | H(13)···C17 | 3.574 (3) |
C20···C14 | 3.170 (3) | H(14)···Cl2 | 3.075 (3) |
C20···C8 | 3.170 (3) | H(14)···Cl3 | 3.173 (3) |
C20···C1 | 3.170 (3) | H(14)···Cl4 | 3.063 (2) |
C20···C2 | 3.170 (3) | H(14)···C20 | 3.257 (3) |
C20···C7 | 3.170 (3) | H(14)···C16 | 3.245 (3) |
C20···C16 | 2.365 (3) | H(14)···C19 | 2.013 (3) |
C20···C16 | 3.170 (3) | H(14)···C17 | 2.036 (3) |
C20···C19 | 3.170 (3) | H(15)···S1 | 1.581 (2) |
C20···C18 | 2.399 (3) | H(15)···Cl1 | 1.581 (2) |
C20···C18 | 3.170 (3) | H(15)···Cl2 | 1.581 (3) |
C20···C17 | 2.760 (3) | H(15)···Cl3 | 1.581 (2) |
C20···C17 | 3.170 (3) | H(15)···Cl4 | 3.085 (2) |
C20···C10 | 3.170 (3) | H(15)···Cl4 | 1.581 (2) |
C20···C9 | 3.170 (3) | H(15)···O2 | 2.951 (3) |
C20···H(1) | 3.170 (3) | H(15)···O2 | 2.865 (3) |
C20···H(2) | 3.170 (3) | H(15)···O2 | 1.581 (3) |
C20···H(3) | 3.170 (3) | H(15)···F1 | 1.581 (3) |
C20···H(4) | 3.170 (3) | H(15)···N3 | 1.581 (3) |
C20···H(5) | 3.170 (3) | H(15)···N2 | 1.581 (3) |
C20···H(6) | 3.170 (3) | H(15)···N1 | 1.581 (3) |
C20···H(7) | 3.475 (3) | H(15)···O1 | 1.581 (3) |
C20···H(7) | 3.170 (3) | H(15)···C12 | 1.581 (3) |
C20···H(8) | 3.170 (3) | H(15)···C13 | 1.581 (3) |
C20···H(9) | 2.701 (3) | H(15)···C15 | 3.288 (3) |
C20···H(9) | 3.170 (3) | H(15)···C15 | 1.581 (3) |
C20···H(10) | 2.709 (3) | H(15)···C3 | 1.581 (3) |
C20···H(10) | 3.170 (3) | H(15)···C5 | 1.581 (3) |
C20···H(11) | 3.170 (3) | H(15)···C4 | 1.581 (3) |
C20···H(12) | 2.924 (3) | H(15)···C11 | 1.581 (3) |
C20···H(12) | 3.170 (3) | H(15)···C20 | 2.048 (3) |
C20···H(13) | 3.170 (3) | H(15)···C20 | 1.581 (3) |
C20···H(14) | 3.257 (3) | H(15)···C6 | 1.581 (3) |
C20···H(14) | 3.170 (3) | H(15)···C14 | 1.581 (3) |
C20···H(15) | 2.048 (3) | H(15)···C8 | 1.581 (3) |
C20···H(15) | 3.170 (3) | H(15)···C1 | 1.581 (3) |
C20···H(16) | 3.170 (3) | H(15)···C2 | 1.581 (3) |
C6···S1 | 2.748 (2) | H(15)···C7 | 1.581 (3) |
C6···N2 | 3.373 (3) | H(15)···C16 | 1.581 (3) |
C6···C4 | 3.240 (3) | H(15)···C19 | 1.581 (3) |
C6···C8 | 2.377 (3) | H(15)···C18 | 2.017 (3) |
C6···C10 | 2.382 (3) | H(15)···C18 | 1.581 (3) |
C6···C9 | 2.751 (3) | H(15)···C17 | 3.239 (3) |
C6···H(2) | 2.063 (3) | H(15)···C17 | 1.581 (3) |
C6···H(4) | 3.240 (3) | H(15)···C10 | 1.581 (3) |
C6···H(7) | 3.316 (3) | H(15)···C9 | 1.581 (3) |
C6···H(10) | 2.846 (3) | H(16)···S1 | 3.006 (2) |
C6···H(11) | 3.568 (3) | H(16)···Cl1 | 3.006 (2) |
C14···S1 | 3.207 (2) | H(16)···Cl2 | 3.006 (2) |
C14···N3 | 2.453 (3) | H(16)···Cl3 | 3.006 (2) |
C14···C12 | 2.831 (3) | H(16)···Cl4 | 3.006 (2) |
C14···C5 | 3.162 (3) | H(16)···O2 | 2.958 (3) |
C14···C4 | 2.493 (3) | H(16)···O2 | 3.006 (3) |
C14···C11 | 2.430 (3) | H(16)···F1 | 3.006 (2) |
C14···C10 | 3.520 (3) | H(16)···N3 | 2.676 (2) |
C14···H(5) | 2.639 (3) | H(16)···N3 | 3.006 (3) |
C14···H(6) | 3.248 (3) | H(16)···N2 | 3.006 (3) |
C14···H(7) | 3.127 (3) | H(16)···N1 | 3.294 (3) |
C14···H(9) | 2.048 (3) | H(16)···N1 | 3.006 (3) |
C14···H(10) | 2.041 (3) | H(16)···O1 | 2.896 (3) |
C8···C5 | 2.746 (3) | H(16)···O1 | 3.006 (3) |
C8···C6 | 2.377 (3) | H(16)···C12 | 3.006 (3) |
C8···C10 | 2.381 (3) | H(16)···C13 | 2.462 (3) |
C8···H(1) | 3.237 (3) | H(16)···C13 | 3.006 (3) |
C8···H(2) | 2.019 (3) | H(16)···C15 | 2.036 (3) |
C8···H(3) | 2.007 (4) | H(16)···C15 | 3.006 (3) |
C8···H(4) | 3.239 (3) | H(16)···C3 | 3.006 (3) |
C8···H(10) | 3.041 (3) | H(16)···C5 | 3.006 (3) |
C8···H(16) | 3.552 (3) | H(16)···C4 | 3.006 (3) |
C1···Cl3 | 2.623 (2) | H(16)···C11 | 3.006 (3) |
C1···N1 | 3.437 (3) | H(16)···C20 | 3.006 (3) |
C1···O1 | 3.489 (3) | H(16)···C6 | 3.006 (3) |
C1···C3 | 2.458 (3) | H(16)···C14 | 3.006 (3) |
C1···C4 | 3.257 (3) | H(16)···C8 | 3.552 (3) |
C2···S1 | 3.072 (2) | H(16)···C8 | 3.006 (3) |
C2···Cl1 | 2.644 (2) | H(16)···C1 | 3.006 (3) |
C2···Cl2 | 2.679 (2) | H(16)···C2 | 3.006 (3) |
C2···O2 | 3.545 (3) | H(16)···C7 | 3.006 (3) |
C2···N1 | 2.413 (3) | H(16)···C16 | 3.230 (3) |
C2···O1 | 2.630 (3) | H(16)···C16 | 3.006 (3) |
C2···C4 | 2.520 (3) | H(16)···C19 | 2.043 (3) |
C7···Cl4 | 2.680 (2) | H(16)···C19 | 3.006 (3) |
C7···F1 | 3.584 (3) | H(16)···C18 | 3.248 (3) |
C7···N3 | 3.558 (3) | H(16)···C18 | 3.006 (3) |
C7···C5 | 2.404 (3) | H(16)···C17 | 3.006 (3) |
C7···C10 | 2.773 (3) | H(16)···C10 | 3.006 (3) |
C7···C9 | 2.384 (4) | H(16)···C9 | 3.006 (3) |
C5—S1—C4 | 103.58 (9) | C19—C20—C15 | 121.3 (2) |
C12—N3—C13 | 110.2 (2) | H(16)—C20—C15 | 119.5 (2) |
C12—N3—C15 | 112.8 (2) | C7—C6—H(1) | 119.8 (3) |
C13—N3—C15 | 113.8 (1) | C7—C6—C5 | 120.6 (2) |
C4—N2—C11 | 122.4 (2) | H(1)—C6—C5 | 119.5 (2) |
C4—N2—C14 | 125.3 (2) | H(11)—C14—H(12) | 109.5 (3) |
C11—N2—C14 | 112.0 (2) | H(11)—C14—N2 | 108.5 (2) |
O1—N1—C3 | 118.3 (2) | H(11)—C14—C13 | 108.9 (2) |
O1—N1—O2 | 121.5 (2) | H(12)—C14—N2 | 109.5 (2) |
C3—N1—O2 | 120.1 (2) | H(12)—C14—C13 | 109.0 (2) |
C11—C12—H(7) | 108.3 (2) | N2—C14—C13 | 111.5 (2) |
C11—C12—H(8) | 109.6 (2) | C7—C8—C9 | 121.9 (2) |
C11—C12—N3 | 111.7 (2) | C7—C8—Cl4 | 118.7 (2) |
H(7)—C12—H(8) | 109.5 (3) | C9—C8—Cl4 | 119.4 (2) |
H(7)—C12—N3 | 109.0 (2) | C2—C1—Cl1 | 122.4 (2) |
H(8)—C12—N3 | 108.7 (2) | C2—C1—Cl2 | 123.0 (2) |
C14—C13—H(9) | 109.8 (2) | Cl1—C1—Cl2 | 114.6 (1) |
C14—C13—H(10) | 109.2 (2) | Cl3—C2—C3 | 117.5 (2) |
C14—C13—N3 | 110.3 (2) | Cl3—C2—C1 | 117.3 (2) |
H(9)—C13—H(10) | 109.5 (2) | C3—C2—C1 | 125.2 (2) |
H(9)—C13—N3 | 109.0 (2) | H(2)—C7—C6 | 121.9 (3) |
H(10)—C13—N3 | 109.1 (2) | H(2)—C7—C8 | 119.7 (3) |
C20—C15—C16 | 116.3 (2) | C6—C7—C8 | 118.3 (2) |
C20—C15—N3 | 123.6 (2) | C17—C16—F1 | 118.2 (2) |
C16—C15—N3 | 120.0 (2) | C17—C16—C15 | 122.9 (2) |
C4—C3—C2 | 124.9 (2) | F1—C16—C15 | 118.9 (2) |
C4—C3—N1 | 121.0 (2) | C18—C19—H(15) | 120.1 (2) |
C2—C3—N1 | 113.9 (2) | C18—C19—C20 | 120.1 (2) |
C6—C5—C10 | 120.0 (2) | H(15)—C19—C20 | 119.7 (3) |
C6—C5—S1 | 120.8 (2) | C17—C18—H(14) | 120.4 (3) |
C10—C5—S1 | 119.2 (2) | C17—C18—C19 | 119.9 (2) |
S1—C4—N2 | 121.1 (1) | H(14)—C18—C19 | 119.7 (3) |
S1—C4—C3 | 114.7 (1) | H(13)—C17—C16 | 120.5 (3) |
N2—C4—C3 | 124.2 (2) | H(13)—C17—C18 | 120.2 (3) |
H(5)—C11—H(6) | 109.5 (3) | C16—C17—C18 | 119.3 (2) |
H(5)—C11—N2 | 109.6 (2) | C9—C10—H(4) | 120.5 (3) |
H(5)—C11—C12 | 109.1 (2) | C9—C10—C5 | 119.3 (2) |
H(6)—C11—N2 | 110.1 (2) | H(4)—C10—C5 | 120.2 (3) |
H(6)—C11—C12 | 109.9 (2) | H(3)—C9—C8 | 119.9 (3) |
N2—C11—C12 | 108.6 (2) | H(3)—C9—C10 | 120.3 (3) |
C19—C20—H(16) | 119.2 (2) | C8—C9—C10 | 119.7 (2) |
C4—S1—C5—C6 | 56.7 (2) | N3—C15—C20—H(16) | 1.4 (4) |
C4—S1—C5—C10 | −125.6 (2) | C16—C15—C20—C19 | 2.5 (3) |
C5—S1—C4—N2 | 37.5 (2) | C16—C15—C20—H(16) | −177.2 (2) |
C5—S1—C4—C3 | −142.3 (1) | N3—C15—C16—F1 | −2.5 (3) |
C13—N3—C12—C11 | −58.6 (2) | N3—C15—C16—C17 | 178.2 (2) |
C13—N3—C12—H(7) | 61.0 (2) | C20—C15—C16—F1 | 176.1 (2) |
C13—N3—C12—H(8) | −179.7 (2) | C20—C15—C16—C17 | −3.1 (3) |
C15—N3—C12—C11 | 173.0 (2) | N1—C3—C4—S1 | −145.2 (2) |
C15—N3—C12—H(7) | −67.3 (2) | N1—C3—C4—N2 | 35.0 (3) |
C15—N3—C12—H(8) | 52.0 (3) | C2—C3—C4—S1 | 30.5 (3) |
C12—N3—C13—C14 | 55.9 (2) | C2—C3—C4—N2 | −149.3 (2) |
C12—N3—C13—H(9) | 176.5 (2) | N1—C3—C2—Cl3 | 65.4 (2) |
C12—N3—C13—H(10) | −64.0 (2) | N1—C3—C2—C1 | −115.1 (2) |
C15—N3—C13—C14 | −176.3 (2) | C4—C3—C2—Cl3 | −110.5 (2) |
C15—N3—C13—H(9) | −55.7 (3) | C4—C3—C2—C1 | 69.0 (3) |
C15—N3—C13—H(10) | 63.8 (2) | S1—C5—C6—C7 | −177.5 (2) |
C12—N3—C15—C20 | 118.4 (2) | S1—C5—C6—H(1) | 0.4 (4) |
C12—N3—C15—C16 | −63.0 (2) | C10—C5—C6—C7 | 4.8 (3) |
C13—N3—C15—C20 | −8.0 (3) | C10—C5—C6—H(1) | −177.3 (3) |
C13—N3—C15—C16 | 170.6 (2) | S1—C5—C10—C9 | 178.5 (2) |
C11—N2—C4—S1 | −153.8 (1) | S1—C5—C10—H(4) | −1.7 (4) |
C11—N2—C4—C3 | 26.0 (3) | C6—C5—C10—C9 | −3.8 (3) |
C14—N2—C4—S1 | 33.5 (3) | C6—C5—C10—H(4) | 176.0 (3) |
C14—N2—C4—C3 | −146.8 (2) | C15—C20—C19—C18 | −0.1 (3) |
C4—N2—C11—C12 | 129.8 (2) | C15—C20—C19—H(15) | 179.5 (3) |
C4—N2—C11—H(5) | −111.1 (2) | H(16)—C20—C19—C18 | 179.6 (3) |
C4—N2—C11—H(6) | 9.4 (3) | H(16)—C20—C19—H(15) | −0.8 (4) |
C14—N2—C11—C12 | −56.6 (2) | C5—C6—C7—C8 | −2.7 (3) |
C14—N2—C11—H(5) | 62.5 (2) | C5—C6—C7—H(2) | −179.8 (3) |
C14—N2—C11—H(6) | −177.0 (2) | H(1)—C6—C7—C8 | 179.4 (3) |
C4—N2—C14—C13 | −130.2 (2) | H(1)—C6—C7—H(2) | 2.3 (4) |
C4—N2—C14—H(11) | −10.3 (3) | Cl4—C8—C7—C6 | 177.2 (2) |
C4—N2—C14—H(12) | 109.1 (2) | Cl4—C8—C7—H(2) | −5.6 (4) |
C11—N2—C14—C13 | 56.4 (2) | C9—C8—C7—C6 | −0.5 (4) |
C11—N2—C14—H(11) | 176.3 (2) | C9—C8—C7—H(2) | 176.7 (3) |
C11—N2—C14—H(12) | −64.3 (2) | Cl4—C8—C9—C10 | −176.3 (2) |
O2—N1—C3—C4 | 13.3 (3) | Cl4—C8—C9—H(3) | 3.6 (4) |
O2—N1—C3—C2 | −162.9 (2) | C7—C8—C9—C10 | 1.4 (4) |
O1—N1—C3—C4 | −170.1 (2) | C7—C8—C9—H(3) | −178.7 (3) |
O1—N1—C3—C2 | 13.8 (3) | Cl1—C1—C2—Cl3 | −177.7 (2) |
N3—C12—C11—N2 | 58.1 (2) | Cl1—C1—C2—C3 | 2.8 (3) |
N3—C12—C11—H(5) | −61.3 (3) | Cl2—C1—C2—Cl3 | 2.0 (3) |
N3—C12—C11—H(6) | 178.7 (2) | Cl2—C1—C2—C3 | −177.5 (2) |
H(7)—C12—C11—N2 | −62.0 (3) | F1—C16—C17—C18 | −177.9 (2) |
H(7)—C12—C11—H(5) | 178.6 (3) | F1—C16—C17—H(13) | 3.1 (4) |
H(7)—C12—C11—H(6) | 58.6 (3) | C15—C16—C17—C18 | 1.3 (4) |
H(8)—C12—C11—N2 | 178.7 (2) | C15—C16—C17—H(13) | −177.7 (3) |
H(8)—C12—C11—H(5) | 59.2 (3) | C20—C19—C18—C17 | −1.9 (4) |
H(8)—C12—C11—H(6) | −60.8 (3) | C20—C19—C18—H(14) | 178.6 (3) |
N3—C13—C14—N2 | −55.0 (2) | H(15)—C19—C18—C17 | 178.6 (3) |
N3—C13—C14—H(11) | −174.7 (2) | H(15)—C19—C18—H(14) | −0.9 (5) |
N3—C13—C14—H(12) | 65.9 (3) | C19—C18—C17—C16 | 1.3 (4) |
H(9)—C13—C14—N2 | −175.2 (2) | C19—C18—C17—H(13) | −179.8 (3) |
H(9)—C13—C14—H(11) | 65.1 (3) | H(14)—C18—C17—C16 | −179.2 (3) |
H(9)—C13—C14—H(12) | −54.2 (3) | H(14)—C18—C17—H(13) | −0.2 (5) |
H(10)—C13—C14—N2 | 64.8 (3) | C5—C10—C9—C8 | 0.8 (4) |
H(10)—C13—C14—H(11) | −54.9 (3) | C5—C10—C9—H(3) | −179.2 (3) |
H(10)—C13—C14—H(12) | −174.2 (3) | H(4)—C10—C9—C8 | −179.1 (3) |
N3—C15—C20—C19 | −178.9 (2) | H(4)—C10—C9—H(3) | 1.0 (5) |