Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803022001/rn6000sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803022001/rn6000Isup2.hkl |
CCDC reference: 226957
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.061
- wR factor = 0.126
- Data-to-parameter ratio = 15.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for N1 - C7 = 5.16 su PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
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 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.
C36H29Cl2N3O3 | Dx = 1.384 Mg m−3 |
Mr = 622.52 | Melting point = 524–525 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 12.622 (4) Å | Cell parameters from 851 reflections |
b = 9.644 (3) Å | θ = 2.7–23.8° |
c = 24.576 (9) Å | µ = 0.26 mm−1 |
β = 92.958 (6)° | T = 293 K |
V = 2987.7 (17) Å3 | Plate, colorless |
Z = 4 | 0.20 × 0.16 × 0.10 mm |
F(000) = 1296 |
Bruker SMART CCD area-detector diffractometer | 6082 independent reflections |
Radiation source: fine-focus sealed tube | 3405 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
φ and ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −15→12 |
Tmin = 0.873, Tmax = 0.974 | k = −11→12 |
16632 measured reflections | l = −30→22 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.061 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.126 | (Δ/σ)max = 0.001 |
S = 1.03 | Δρmax = 0.34 e Å−3 |
6082 reflections | Δρmin = −0.27 e Å−3 |
398 parameters |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.44995 (8) | 0.43251 (10) | 0.22742 (4) | 0.0627 (3) | |
Cl2 | 0.20671 (7) | 0.54749 (12) | 0.39733 (4) | 0.0737 (3) | |
N1 | 0.39840 (19) | 0.3499 (3) | 0.38121 (11) | 0.0426 (7) | |
N2 | 0.92074 (19) | 0.5533 (2) | 0.43535 (10) | 0.0415 (7) | |
H2 | 0.9494 | 0.6047 | 0.4607 | 0.050* | |
N3 | 0.89204 (19) | 0.2556 (2) | 0.35573 (10) | 0.0367 (6) | |
O1 | 0.62952 (16) | 0.2584 (2) | 0.32914 (8) | 0.0457 (6) | |
O2 | 0.48897 (16) | 0.3333 (2) | 0.41630 (8) | 0.0436 (6) | |
O3 | 0.96250 (16) | 0.3417 (2) | 0.47210 (9) | 0.0468 (6) | |
C1 | 0.6499 (2) | 0.3143 (3) | 0.37202 (12) | 0.0314 (7) | |
C2 | 0.5750 (2) | 0.4207 (3) | 0.39707 (12) | 0.0333 (7) | |
C3 | 0.6381 (2) | 0.4729 (3) | 0.44675 (12) | 0.0376 (7) | |
H3A | 0.5918 | 0.5000 | 0.4752 | 0.045* | |
H3B | 0.6820 | 0.5513 | 0.4378 | 0.045* | |
C4 | 0.7064 (2) | 0.3473 (3) | 0.46435 (11) | 0.0362 (7) | |
H4A | 0.7658 | 0.3758 | 0.4884 | 0.043* | |
H4B | 0.6646 | 0.2797 | 0.4831 | 0.043* | |
C5 | 0.7455 (2) | 0.2863 (3) | 0.41145 (11) | 0.0297 (7) | |
C6 | 0.5209 (2) | 0.5182 (3) | 0.35495 (12) | 0.0333 (7) | |
H6 | 0.5568 | 0.5095 | 0.3207 | 0.040* | |
C7 | 0.4135 (2) | 0.4483 (3) | 0.34806 (12) | 0.0343 (7) | |
C8 | 0.3265 (2) | 0.4962 (3) | 0.31031 (13) | 0.0392 (8) | |
C9 | 0.3363 (3) | 0.4997 (3) | 0.25426 (14) | 0.0474 (8) | |
C10 | 0.2587 (3) | 0.5528 (4) | 0.21889 (15) | 0.0669 (11) | |
H10 | 0.2680 | 0.5537 | 0.1816 | 0.080* | |
C11 | 0.1685 (3) | 0.6037 (4) | 0.23889 (18) | 0.0701 (12) | |
H11 | 0.1165 | 0.6417 | 0.2152 | 0.084* | |
C12 | 0.1528 (3) | 0.5999 (4) | 0.29342 (17) | 0.0609 (10) | |
H12 | 0.0899 | 0.6328 | 0.3067 | 0.073* | |
C13 | 0.2310 (2) | 0.5471 (3) | 0.32862 (14) | 0.0465 (8) | |
C14 | 0.5078 (2) | 0.6703 (3) | 0.36731 (13) | 0.0353 (7) | |
C15 | 0.4586 (3) | 0.7158 (3) | 0.41262 (15) | 0.0488 (9) | |
H15 | 0.4376 | 0.6516 | 0.4381 | 0.059* | |
C16 | 0.4399 (3) | 0.8549 (4) | 0.42092 (16) | 0.0597 (10) | |
H16 | 0.4065 | 0.8840 | 0.4518 | 0.072* | |
C17 | 0.4708 (3) | 0.9503 (4) | 0.38330 (18) | 0.0634 (11) | |
H17 | 0.4574 | 1.0441 | 0.3884 | 0.076* | |
C18 | 0.5210 (3) | 0.9076 (4) | 0.33854 (17) | 0.0621 (10) | |
H18 | 0.5433 | 0.9723 | 0.3135 | 0.075* | |
C19 | 0.5388 (2) | 0.7679 (3) | 0.33026 (14) | 0.0483 (9) | |
H19 | 0.5721 | 0.7392 | 0.2993 | 0.058* | |
C20 | 0.8453 (2) | 0.3627 (3) | 0.38846 (11) | 0.0315 (7) | |
C21 | 0.8273 (2) | 0.4954 (3) | 0.35701 (12) | 0.0321 (7) | |
C22 | 0.7853 (2) | 0.5198 (3) | 0.30521 (12) | 0.0409 (8) | |
H22 | 0.7575 | 0.4471 | 0.2841 | 0.049* | |
C23 | 0.7847 (3) | 0.6529 (4) | 0.28492 (13) | 0.0499 (9) | |
H23 | 0.7564 | 0.6700 | 0.2499 | 0.060* | |
C24 | 0.8256 (3) | 0.7605 (4) | 0.31604 (15) | 0.0544 (10) | |
H24 | 0.8226 | 0.8502 | 0.3022 | 0.065* | |
C25 | 0.8708 (3) | 0.7374 (3) | 0.36739 (14) | 0.0476 (9) | |
H25 | 0.8995 | 0.8100 | 0.3883 | 0.057* | |
C26 | 0.8721 (2) | 0.6046 (3) | 0.38672 (12) | 0.0344 (7) | |
C27 | 0.9171 (2) | 0.4146 (3) | 0.43746 (12) | 0.0350 (7) | |
C28 | 0.8872 (2) | 0.1274 (3) | 0.38683 (13) | 0.0415 (8) | |
H28A | 0.9426 | 0.1251 | 0.4157 | 0.050* | |
H28B | 0.8951 | 0.0475 | 0.3634 | 0.050* | |
C29 | 0.7778 (2) | 0.1289 (3) | 0.41042 (12) | 0.0348 (7) | |
H29 | 0.7292 | 0.0836 | 0.3836 | 0.042* | |
C30 | 0.7738 (2) | 0.0455 (3) | 0.46263 (12) | 0.0354 (7) | |
C31 | 0.7103 (3) | −0.0696 (3) | 0.46385 (14) | 0.0488 (9) | |
H31 | 0.6681 | −0.0934 | 0.4331 | 0.059* | |
C32 | 0.7081 (3) | −0.1514 (4) | 0.51041 (16) | 0.0590 (10) | |
H32 | 0.6643 | −0.2289 | 0.5105 | 0.071* | |
C33 | 0.7694 (3) | −0.1192 (4) | 0.55574 (15) | 0.0579 (10) | |
H33 | 0.7680 | −0.1745 | 0.5867 | 0.069* | |
C34 | 0.8328 (3) | −0.0050 (4) | 0.55531 (15) | 0.0580 (10) | |
H34 | 0.8746 | 0.0182 | 0.5863 | 0.070* | |
C35 | 0.8357 (3) | 0.0767 (4) | 0.50916 (14) | 0.0526 (9) | |
H35 | 0.8799 | 0.1538 | 0.5094 | 0.063* | |
C36 | 0.9971 (3) | 0.2876 (3) | 0.33692 (15) | 0.0558 (10) | |
H36A | 0.9938 | 0.3715 | 0.3159 | 0.084* | |
H36B | 1.0206 | 0.2128 | 0.3147 | 0.084* | |
H36C | 1.0461 | 0.2994 | 0.3678 | 0.084* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0785 (7) | 0.0703 (6) | 0.0407 (5) | −0.0064 (5) | 0.0159 (5) | −0.0058 (5) |
Cl2 | 0.0514 (6) | 0.1156 (9) | 0.0549 (6) | 0.0077 (5) | 0.0092 (5) | −0.0127 (6) |
N1 | 0.0373 (15) | 0.0485 (16) | 0.0417 (17) | −0.0013 (13) | 0.0000 (13) | 0.0059 (14) |
N2 | 0.0519 (16) | 0.0283 (14) | 0.0423 (17) | −0.0070 (12) | −0.0152 (13) | −0.0041 (12) |
N3 | 0.0454 (16) | 0.0296 (13) | 0.0361 (16) | 0.0000 (11) | 0.0102 (12) | −0.0022 (12) |
O1 | 0.0535 (14) | 0.0507 (13) | 0.0319 (13) | 0.0043 (11) | −0.0068 (11) | −0.0114 (11) |
O2 | 0.0419 (12) | 0.0492 (13) | 0.0400 (13) | −0.0025 (10) | 0.0050 (10) | 0.0164 (11) |
O3 | 0.0563 (14) | 0.0354 (12) | 0.0462 (14) | −0.0029 (10) | −0.0216 (11) | 0.0057 (11) |
C1 | 0.0382 (17) | 0.0304 (16) | 0.0257 (17) | −0.0032 (13) | 0.0028 (14) | 0.0005 (14) |
C2 | 0.0367 (16) | 0.0349 (17) | 0.0288 (17) | −0.0021 (14) | 0.0060 (13) | 0.0025 (14) |
C3 | 0.0466 (19) | 0.0381 (18) | 0.0287 (17) | 0.0064 (14) | 0.0086 (14) | −0.0053 (14) |
C4 | 0.0431 (18) | 0.0430 (18) | 0.0225 (16) | 0.0032 (15) | 0.0012 (13) | −0.0009 (14) |
C5 | 0.0347 (17) | 0.0295 (16) | 0.0246 (16) | 0.0010 (13) | −0.0018 (13) | −0.0014 (13) |
C6 | 0.0348 (17) | 0.0372 (17) | 0.0282 (16) | 0.0003 (13) | 0.0053 (13) | 0.0056 (14) |
C7 | 0.0409 (18) | 0.0331 (17) | 0.0293 (17) | −0.0020 (14) | 0.0051 (14) | 0.0031 (14) |
C8 | 0.0403 (18) | 0.0377 (18) | 0.0390 (19) | −0.0064 (14) | −0.0043 (15) | −0.0001 (15) |
C9 | 0.056 (2) | 0.047 (2) | 0.039 (2) | −0.0117 (17) | −0.0030 (17) | 0.0026 (17) |
C10 | 0.078 (3) | 0.084 (3) | 0.037 (2) | −0.011 (2) | −0.012 (2) | 0.008 (2) |
C11 | 0.070 (3) | 0.071 (3) | 0.066 (3) | 0.001 (2) | −0.028 (2) | 0.008 (2) |
C12 | 0.042 (2) | 0.062 (2) | 0.078 (3) | 0.0057 (17) | −0.012 (2) | 0.000 (2) |
C13 | 0.042 (2) | 0.049 (2) | 0.048 (2) | −0.0051 (16) | −0.0030 (17) | −0.0027 (17) |
C14 | 0.0329 (16) | 0.0325 (17) | 0.040 (2) | −0.0006 (13) | −0.0007 (14) | 0.0065 (15) |
C15 | 0.054 (2) | 0.039 (2) | 0.054 (2) | 0.0006 (16) | 0.0149 (18) | 0.0045 (17) |
C16 | 0.062 (2) | 0.045 (2) | 0.073 (3) | 0.0063 (18) | 0.017 (2) | −0.003 (2) |
C17 | 0.064 (2) | 0.036 (2) | 0.090 (3) | 0.0077 (18) | 0.002 (2) | 0.004 (2) |
C18 | 0.070 (3) | 0.044 (2) | 0.072 (3) | −0.0019 (19) | 0.006 (2) | 0.021 (2) |
C19 | 0.047 (2) | 0.048 (2) | 0.050 (2) | 0.0002 (16) | 0.0021 (17) | 0.0108 (18) |
C20 | 0.0375 (17) | 0.0279 (16) | 0.0287 (17) | −0.0007 (13) | −0.0007 (13) | −0.0016 (13) |
C21 | 0.0361 (16) | 0.0305 (16) | 0.0299 (17) | −0.0006 (13) | 0.0040 (13) | 0.0004 (14) |
C22 | 0.051 (2) | 0.0398 (19) | 0.0313 (18) | −0.0048 (15) | 0.0003 (15) | 0.0000 (15) |
C23 | 0.058 (2) | 0.058 (2) | 0.034 (2) | −0.0044 (18) | 0.0007 (16) | 0.0186 (18) |
C24 | 0.063 (2) | 0.042 (2) | 0.058 (3) | −0.0080 (18) | −0.002 (2) | 0.0218 (19) |
C25 | 0.058 (2) | 0.0294 (17) | 0.054 (2) | −0.0089 (15) | −0.0081 (18) | 0.0038 (16) |
C26 | 0.0365 (17) | 0.0314 (17) | 0.0349 (18) | −0.0017 (13) | −0.0026 (14) | 0.0014 (14) |
C27 | 0.0389 (18) | 0.0303 (17) | 0.0353 (18) | −0.0054 (14) | −0.0020 (15) | 0.0007 (15) |
C28 | 0.052 (2) | 0.0267 (17) | 0.046 (2) | 0.0019 (14) | 0.0069 (16) | −0.0018 (15) |
C29 | 0.0410 (17) | 0.0288 (16) | 0.0342 (18) | −0.0032 (13) | −0.0018 (14) | 0.0001 (14) |
C30 | 0.0377 (17) | 0.0279 (16) | 0.0404 (19) | 0.0005 (14) | 0.0002 (14) | 0.0041 (14) |
C31 | 0.061 (2) | 0.042 (2) | 0.044 (2) | −0.0110 (17) | 0.0021 (17) | −0.0004 (17) |
C32 | 0.079 (3) | 0.038 (2) | 0.061 (3) | −0.0148 (18) | 0.012 (2) | 0.0078 (19) |
C33 | 0.072 (3) | 0.049 (2) | 0.053 (2) | 0.0064 (19) | 0.005 (2) | 0.0201 (19) |
C34 | 0.056 (2) | 0.065 (2) | 0.051 (2) | 0.000 (2) | −0.0108 (18) | 0.020 (2) |
C35 | 0.053 (2) | 0.050 (2) | 0.053 (2) | −0.0137 (17) | −0.0107 (18) | 0.0131 (19) |
C36 | 0.056 (2) | 0.049 (2) | 0.064 (3) | 0.0009 (17) | 0.0224 (19) | −0.0027 (19) |
Cl1—C9 | 1.735 (4) | C15—C16 | 1.379 (4) |
Cl2—C13 | 1.732 (4) | C15—H15 | 0.9300 |
N1—C7 | 1.271 (3) | C16—C17 | 1.376 (5) |
N1—O2 | 1.405 (3) | C16—H16 | 0.9300 |
N2—C27 | 1.340 (4) | C17—C18 | 1.362 (5) |
N2—C26 | 1.405 (4) | C17—H17 | 0.9300 |
N2—H2 | 0.8600 | C18—C19 | 1.383 (5) |
N3—C20 | 1.453 (3) | C18—H18 | 0.9300 |
N3—C28 | 1.457 (4) | C19—H19 | 0.9300 |
N3—C36 | 1.460 (4) | C20—C21 | 1.507 (4) |
O1—C1 | 1.200 (3) | C20—C27 | 1.552 (4) |
O2—C2 | 1.472 (3) | C21—C22 | 1.374 (4) |
O3—C27 | 1.223 (3) | C21—C26 | 1.385 (4) |
C1—C5 | 1.532 (4) | C22—C23 | 1.377 (4) |
C1—C2 | 1.544 (4) | C22—H22 | 0.9300 |
C2—C3 | 1.509 (4) | C23—C24 | 1.374 (5) |
C2—C6 | 1.533 (4) | C23—H23 | 0.9300 |
C3—C4 | 1.536 (4) | C24—C25 | 1.376 (5) |
C3—H3A | 0.9700 | C24—H24 | 0.9300 |
C3—H3B | 0.9700 | C25—C26 | 1.366 (4) |
C4—C5 | 1.531 (4) | C25—H25 | 0.9300 |
C4—H4A | 0.9700 | C28—C29 | 1.525 (4) |
C4—H4B | 0.9700 | C28—H28A | 0.9700 |
C5—C29 | 1.573 (4) | C28—H28B | 0.9700 |
C5—C20 | 1.588 (4) | C29—C30 | 1.517 (4) |
C6—C14 | 1.509 (4) | C29—H29 | 0.9800 |
C6—C7 | 1.515 (4) | C30—C31 | 1.370 (4) |
C6—H6 | 0.9800 | C30—C35 | 1.384 (4) |
C7—C8 | 1.475 (4) | C31—C32 | 1.391 (4) |
C8—C9 | 1.390 (4) | C31—H31 | 0.9300 |
C8—C13 | 1.397 (4) | C32—C33 | 1.359 (5) |
C9—C10 | 1.375 (5) | C32—H32 | 0.9300 |
C10—C11 | 1.356 (5) | C33—C34 | 1.362 (5) |
C10—H10 | 0.9300 | C33—H33 | 0.9300 |
C11—C12 | 1.365 (5) | C34—C35 | 1.383 (4) |
C11—H11 | 0.9300 | C34—H34 | 0.9300 |
C12—C13 | 1.376 (4) | C35—H35 | 0.9300 |
C12—H12 | 0.9300 | C36—H36A | 0.9600 |
C14—C15 | 1.374 (4) | C36—H36B | 0.9600 |
C14—C19 | 1.380 (4) | C36—H36C | 0.9600 |
C7—N1—O2 | 109.5 (2) | C18—C17—H17 | 120.0 |
C27—N2—C26 | 111.7 (2) | C16—C17—H17 | 120.0 |
C27—N2—H2 | 124.1 | C17—C18—C19 | 120.0 (3) |
C26—N2—H2 | 124.1 | C17—C18—H18 | 120.0 |
C20—N3—C28 | 106.5 (2) | C19—C18—H18 | 120.0 |
C20—N3—C36 | 115.3 (2) | C14—C19—C18 | 120.9 (3) |
C28—N3—C36 | 114.1 (2) | C14—C19—H19 | 119.5 |
N1—O2—C2 | 109.1 (2) | C18—C19—H19 | 119.5 |
O1—C1—C5 | 127.0 (3) | N3—C20—C21 | 112.0 (2) |
O1—C1—C2 | 122.8 (3) | N3—C20—C27 | 114.9 (2) |
C5—C1—C2 | 110.1 (2) | C21—C20—C27 | 101.0 (2) |
O2—C2—C3 | 107.4 (2) | N3—C20—C5 | 102.7 (2) |
O2—C2—C6 | 104.9 (2) | C21—C20—C5 | 118.3 (2) |
C3—C2—C6 | 122.7 (2) | C27—C20—C5 | 108.4 (2) |
O2—C2—C1 | 103.0 (2) | C22—C21—C26 | 119.1 (3) |
C3—C2—C1 | 103.6 (2) | C22—C21—C20 | 131.4 (3) |
C6—C2—C1 | 113.5 (2) | C26—C21—C20 | 109.2 (2) |
C2—C3—C4 | 103.3 (2) | C21—C22—C23 | 119.3 (3) |
C2—C3—H3A | 111.1 | C21—C22—H22 | 120.3 |
C4—C3—H3A | 111.1 | C23—C22—H22 | 120.3 |
C2—C3—H3B | 111.1 | C24—C23—C22 | 120.5 (3) |
C4—C3—H3B | 111.1 | C24—C23—H23 | 119.7 |
H3A—C3—H3B | 109.1 | C22—C23—H23 | 119.7 |
C5—C4—C3 | 105.3 (2) | C23—C24—C25 | 121.0 (3) |
C5—C4—H4A | 110.7 | C23—C24—H24 | 119.5 |
C3—C4—H4A | 110.7 | C25—C24—H24 | 119.5 |
C5—C4—H4B | 110.7 | C26—C25—C24 | 117.9 (3) |
C3—C4—H4B | 110.7 | C26—C25—H25 | 121.1 |
H4A—C4—H4B | 108.8 | C24—C25—H25 | 121.1 |
C4—C5—C1 | 101.1 (2) | C25—C26—C21 | 122.1 (3) |
C4—C5—C29 | 118.6 (2) | C25—C26—N2 | 128.5 (3) |
C1—C5—C29 | 110.9 (2) | C21—C26—N2 | 109.2 (2) |
C4—C5—C20 | 114.9 (2) | O3—C27—N2 | 125.8 (3) |
C1—C5—C20 | 107.9 (2) | O3—C27—C20 | 126.0 (3) |
C29—C5—C20 | 103.3 (2) | N2—C27—C20 | 108.2 (2) |
C14—C6—C7 | 110.4 (2) | N3—C28—C29 | 104.8 (2) |
C14—C6—C2 | 120.7 (3) | N3—C28—H28A | 110.8 |
C7—C6—C2 | 99.6 (2) | C29—C28—H28A | 110.8 |
C14—C6—H6 | 108.5 | N3—C28—H28B | 110.8 |
C7—C6—H6 | 108.5 | C29—C28—H28B | 110.8 |
C2—C6—H6 | 108.5 | H28A—C28—H28B | 108.9 |
N1—C7—C8 | 120.3 (3) | C30—C29—C28 | 112.8 (2) |
N1—C7—C6 | 115.1 (3) | C30—C29—C5 | 118.5 (2) |
C8—C7—C6 | 124.3 (3) | C28—C29—C5 | 104.8 (2) |
C9—C8—C13 | 115.7 (3) | C30—C29—H29 | 106.7 |
C9—C8—C7 | 122.0 (3) | C28—C29—H29 | 106.7 |
C13—C8—C7 | 122.3 (3) | C5—C29—H29 | 106.7 |
C10—C9—C8 | 122.6 (3) | C31—C30—C35 | 117.6 (3) |
C10—C9—Cl1 | 118.3 (3) | C31—C30—C29 | 119.5 (3) |
C8—C9—Cl1 | 119.1 (3) | C35—C30—C29 | 122.8 (3) |
C11—C10—C9 | 119.4 (4) | C30—C31—C32 | 120.9 (3) |
C11—C10—H10 | 120.3 | C30—C31—H31 | 119.5 |
C9—C10—H10 | 120.3 | C32—C31—H31 | 119.5 |
C10—C11—C12 | 120.9 (4) | C33—C32—C31 | 120.7 (3) |
C10—C11—H11 | 119.6 | C33—C32—H32 | 119.7 |
C12—C11—H11 | 119.6 | C31—C32—H32 | 119.7 |
C11—C12—C13 | 119.5 (4) | C32—C33—C34 | 119.2 (3) |
C11—C12—H12 | 120.3 | C32—C33—H33 | 120.4 |
C13—C12—H12 | 120.3 | C34—C33—H33 | 120.4 |
C12—C13—C8 | 122.0 (3) | C33—C34—C35 | 120.5 (3) |
C12—C13—Cl2 | 117.0 (3) | C33—C34—H34 | 119.8 |
C8—C13—Cl2 | 120.9 (3) | C35—C34—H34 | 119.8 |
C15—C14—C19 | 118.2 (3) | C34—C35—C30 | 121.1 (3) |
C15—C14—C6 | 122.2 (3) | C34—C35—H35 | 119.5 |
C19—C14—C6 | 119.5 (3) | C30—C35—H35 | 119.5 |
C14—C15—C16 | 121.2 (3) | N3—C36—H36A | 109.5 |
C14—C15—H15 | 119.4 | N3—C36—H36B | 109.5 |
C16—C15—H15 | 119.4 | H36A—C36—H36B | 109.5 |
C17—C16—C15 | 119.7 (3) | N3—C36—H36C | 109.5 |
C17—C16—H16 | 120.2 | H36A—C36—H36C | 109.5 |
C15—C16—H16 | 120.2 | H36B—C36—H36C | 109.5 |
C18—C17—C16 | 120.0 (3) | ||
C7—N1—O2—C2 | −8.6 (3) | C28—N3—C20—C21 | −169.8 (2) |
N1—O2—C2—C3 | 145.1 (2) | C36—N3—C20—C21 | 62.6 (3) |
N1—O2—C2—C6 | 13.1 (3) | C28—N3—C20—C27 | 75.7 (3) |
N1—O2—C2—C1 | −105.9 (2) | C36—N3—C20—C27 | −51.9 (3) |
O1—C1—C2—O2 | 74.1 (3) | C28—N3—C20—C5 | −41.7 (3) |
C5—C1—C2—O2 | −101.9 (2) | C36—N3—C20—C5 | −169.4 (2) |
O1—C1—C2—C3 | −174.1 (3) | C4—C5—C20—N3 | 155.9 (2) |
C5—C1—C2—C3 | 9.9 (3) | C1—C5—C20—N3 | −92.3 (2) |
O1—C1—C2—C6 | −38.8 (4) | C29—C5—C20—N3 | 25.2 (3) |
C5—C1—C2—C6 | 145.2 (2) | C4—C5—C20—C21 | −80.1 (3) |
O2—C2—C3—C4 | 77.7 (3) | C1—C5—C20—C21 | 31.7 (3) |
C6—C2—C3—C4 | −160.9 (3) | C29—C5—C20—C21 | 149.1 (2) |
C1—C2—C3—C4 | −30.9 (3) | C4—C5—C20—C27 | 33.9 (3) |
C2—C3—C4—C5 | 42.1 (3) | C1—C5—C20—C27 | 145.7 (2) |
C3—C4—C5—C1 | −34.5 (3) | C29—C5—C20—C27 | −96.8 (2) |
C3—C4—C5—C29 | −155.9 (2) | N3—C20—C21—C22 | 45.1 (4) |
C3—C4—C5—C20 | 81.3 (3) | C27—C20—C21—C22 | 167.8 (3) |
O1—C1—C5—C4 | −160.6 (3) | C5—C20—C21—C22 | −74.1 (4) |
C2—C1—C5—C4 | 15.2 (3) | N3—C20—C21—C26 | −128.3 (3) |
O1—C1—C5—C29 | −33.9 (4) | C27—C20—C21—C26 | −5.5 (3) |
C2—C1—C5—C29 | 141.8 (2) | C5—C20—C21—C26 | 112.5 (3) |
O1—C1—C5—C20 | 78.5 (3) | C26—C21—C22—C23 | −2.7 (4) |
C2—C1—C5—C20 | −105.7 (2) | C20—C21—C22—C23 | −175.5 (3) |
O2—C2—C6—C14 | 109.0 (3) | C21—C22—C23—C24 | −0.1 (5) |
C3—C2—C6—C14 | −13.6 (4) | C22—C23—C24—C25 | 2.0 (5) |
C1—C2—C6—C14 | −139.3 (3) | C23—C24—C25—C26 | −1.0 (5) |
O2—C2—C6—C7 | −11.8 (3) | C24—C25—C26—C21 | −1.8 (5) |
C3—C2—C6—C7 | −134.3 (3) | C24—C25—C26—N2 | 174.3 (3) |
C1—C2—C6—C7 | 99.9 (3) | C22—C21—C26—C25 | 3.7 (5) |
O2—N1—C7—C8 | −173.9 (2) | C20—C21—C26—C25 | 178.0 (3) |
O2—N1—C7—C6 | 0.1 (3) | C22—C21—C26—N2 | −173.0 (3) |
C14—C6—C7—N1 | −120.2 (3) | C20—C21—C26—N2 | 1.2 (3) |
C2—C6—C7—N1 | 7.7 (3) | C27—N2—C26—C25 | −171.9 (3) |
C14—C6—C7—C8 | 53.5 (4) | C27—N2—C26—C21 | 4.6 (4) |
C2—C6—C7—C8 | −178.5 (3) | C26—N2—C27—O3 | 172.0 (3) |
N1—C7—C8—C9 | −124.0 (3) | C26—N2—C27—C20 | −8.1 (3) |
C6—C7—C8—C9 | 62.5 (4) | N3—C20—C27—O3 | −51.2 (4) |
N1—C7—C8—C13 | 59.1 (4) | C21—C20—C27—O3 | −171.9 (3) |
C6—C7—C8—C13 | −114.3 (3) | C5—C20—C27—O3 | 63.0 (4) |
C13—C8—C9—C10 | 1.6 (5) | N3—C20—C27—N2 | 128.9 (3) |
C7—C8—C9—C10 | −175.5 (3) | C21—C20—C27—N2 | 8.2 (3) |
C13—C8—C9—Cl1 | −177.5 (2) | C5—C20—C27—N2 | −116.9 (3) |
C7—C8—C9—Cl1 | 5.4 (4) | C20—N3—C28—C29 | 41.8 (3) |
C8—C9—C10—C11 | −0.2 (6) | C36—N3—C28—C29 | 170.2 (2) |
Cl1—C9—C10—C11 | 178.9 (3) | N3—C28—C29—C30 | −153.7 (2) |
C9—C10—C11—C12 | −1.6 (6) | N3—C28—C29—C5 | −23.3 (3) |
C10—C11—C12—C13 | 1.8 (6) | C4—C5—C29—C30 | −2.8 (4) |
C11—C12—C13—C8 | −0.3 (5) | C1—C5—C29—C30 | −119.0 (3) |
C11—C12—C13—Cl2 | 179.2 (3) | C20—C5—C29—C30 | 125.6 (3) |
C9—C8—C13—C12 | −1.3 (5) | C4—C5—C29—C28 | −129.6 (3) |
C7—C8—C13—C12 | 175.7 (3) | C1—C5—C29—C28 | 114.1 (3) |
C9—C8—C13—Cl2 | 179.2 (2) | C20—C5—C29—C28 | −1.2 (3) |
C7—C8—C13—Cl2 | −3.7 (4) | C28—C29—C30—C31 | −116.0 (3) |
C7—C6—C14—C15 | 60.4 (4) | C5—C29—C30—C31 | 121.0 (3) |
C2—C6—C14—C15 | −54.9 (4) | C28—C29—C30—C35 | 60.9 (4) |
C7—C6—C14—C19 | −114.7 (3) | C5—C29—C30—C35 | −62.1 (4) |
C2—C6—C14—C19 | 130.0 (3) | C35—C30—C31—C32 | 0.3 (5) |
C19—C14—C15—C16 | 0.4 (5) | C29—C30—C31—C32 | 177.4 (3) |
C6—C14—C15—C16 | −174.7 (3) | C30—C31—C32—C33 | −0.3 (5) |
C14—C15—C16—C17 | 0.0 (5) | C31—C32—C33—C34 | 0.4 (6) |
C15—C16—C17—C18 | −1.0 (6) | C32—C33—C34—C35 | −0.5 (6) |
C16—C17—C18—C19 | 1.4 (6) | C33—C34—C35—C30 | 0.6 (6) |
C15—C14—C19—C18 | 0.1 (5) | C31—C30—C35—C34 | −0.5 (5) |
C6—C14—C19—C18 | 175.4 (3) | C29—C30—C35—C34 | −177.4 (3) |
C17—C18—C19—C14 | −1.0 (5) |