Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806012542/at2026sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806012542/at2026Isup2.hkl |
CCDC reference: 610683
Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C21H16ClN3 | F(000) = 2880 |
Mr = 345.82 | Dx = 1.334 Mg m−3 |
Orthorhombic, Pcab | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2bc 2ac | Cell parameters from 7332 reflections |
a = 8.0836 (10) Å | θ = 2.6–30.6° |
b = 27.952 (4) Å | µ = 0.23 mm−1 |
c = 30.483 (3) Å | T = 296 K |
V = 6887.7 (15) Å3 | Rod-shaped, orange |
Z = 16 | 0.35 × 0.20 × 0.10 mm |
Rigaku R-AXIS RAPID-S diffractometer | 10527 independent reflections |
Radiation source: fine-focus sealed tube | 6382 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.096 |
oscillation scans | θmax = 30.6°, θmin = 2.6° |
Absorption correction: multi-scan (Blessing, 1995) | h = −11→9 |
Tmin = 0.924, Tmax = 0.977 | k = −38→39 |
64891 measured reflections | l = −43→43 |
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)] = 0.108 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.205 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.18 | w = 1/[σ2(Fo2) + (0.0393P)2 + 4.4415P] where P = (Fo2 + 2Fc2)/3 |
10527 reflections | (Δ/σ)max < 0.001 |
555 parameters | Δρmax = 0.30 e Å−3 |
0 restraints | Δρmin = −0.27 e Å−3 |
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 | 0.53752 (14) | 0.34057 (3) | 0.05653 (4) | 0.0753 (3) | |
N1 | 0.8228 (3) | 0.00356 (8) | −0.03756 (9) | 0.0457 (6) | |
N2 | 0.6847 (3) | 0.11924 (8) | −0.00584 (8) | 0.0460 (6) | |
N3 | 0.6155 (3) | 0.13222 (9) | 0.02988 (9) | 0.0504 (6) | |
C1 | 0.7469 (4) | −0.00917 (11) | 0.00167 (11) | 0.0476 (7) | |
C2 | 0.7384 (5) | −0.05417 (12) | 0.02136 (13) | 0.0573 (9) | |
C3 | 0.6592 (5) | −0.05689 (14) | 0.06117 (14) | 0.0658 (10) | |
C4 | 0.5863 (5) | −0.01703 (15) | 0.08010 (13) | 0.0626 (10) | |
C5 | 0.5922 (4) | 0.02752 (13) | 0.06069 (11) | 0.0518 (8) | |
C6 | 0.6773 (4) | 0.03195 (10) | 0.02080 (10) | 0.0448 (7) | |
C7 | 0.7168 (4) | 0.07066 (10) | −0.00856 (10) | 0.0424 (7) | |
C8 | 0.8047 (4) | 0.05199 (10) | −0.04387 (10) | 0.0439 (7) | |
C9 | 0.8684 (4) | 0.07692 (11) | −0.08285 (10) | 0.0456 (7) | |
C10 | 0.9463 (4) | 0.12140 (12) | −0.07811 (13) | 0.0549 (8) | |
C11 | 1.0055 (5) | 0.14513 (15) | −0.11431 (15) | 0.0708 (11) | |
C12 | 0.9900 (6) | 0.12555 (17) | −0.15548 (17) | 0.0810 (13) | |
C13 | 0.9143 (6) | 0.08209 (17) | −0.16038 (15) | 0.0781 (12) | |
C14 | 0.8525 (5) | 0.05785 (13) | −0.12453 (12) | 0.0585 (9) | |
C15 | 0.9194 (5) | −0.03009 (11) | −0.06385 (12) | 0.0597 (9) | |
C16 | 0.5960 (4) | 0.18267 (11) | 0.03304 (10) | 0.0473 (7) | |
C17 | 0.5175 (5) | 0.19923 (12) | 0.07049 (12) | 0.0571 (9) | |
C18 | 0.4978 (5) | 0.24788 (13) | 0.07786 (12) | 0.0585 (9) | |
C19 | 0.5582 (4) | 0.27960 (11) | 0.04745 (11) | 0.0529 (8) | |
C20 | 0.6373 (5) | 0.26400 (12) | 0.00998 (12) | 0.0569 (9) | |
C21 | 0.6569 (5) | 0.21560 (12) | 0.00295 (11) | 0.0542 (8) | |
H2 | 0.790 (4) | −0.0801 (10) | 0.0073 (10) | 0.045 (8)* | |
H3 | 0.649 (5) | −0.0869 (14) | 0.0756 (13) | 0.081 (12)* | |
H4 | 0.529 (5) | −0.0180 (12) | 0.1052 (12) | 0.068 (12)* | |
H5 | 0.543 (4) | 0.0561 (12) | 0.0745 (11) | 0.059 (10)* | |
H10 | 0.960 (4) | 0.1336 (11) | −0.0495 (11) | 0.055 (10)* | |
H11 | 1.059 (5) | 0.1769 (15) | −0.1121 (13) | 0.088 (13)* | |
H12 | 1.040 (5) | 0.1434 (16) | −0.1806 (15) | 0.104 (15)* | |
H13 | 0.900 (5) | 0.0681 (14) | −0.1885 (14) | 0.086 (14)* | |
H14 | 0.801 (4) | 0.0289 (11) | −0.1276 (10) | 0.054 (10)* | |
H15A | 0.9092 | −0.0616 | −0.0517 | 0.090* | |
H15B | 1.0336 | −0.0206 | −0.0637 | 0.090* | |
H15C | 0.8789 | −0.0301 | −0.0935 | 0.090* | |
H17 | 0.483 (4) | 0.1755 (12) | 0.0915 (12) | 0.065 (10)* | |
H18 | 0.444 (5) | 0.2578 (13) | 0.1043 (12) | 0.073 (11)* | |
H20 | 0.683 (5) | 0.2888 (13) | −0.0094 (12) | 0.075 (11)* | |
H21 | 0.707 (4) | 0.2034 (12) | −0.0228 (11) | 0.066 (11)* | |
Cl1' | 0.64881 (15) | −0.04734 (3) | −0.18667 (4) | 0.0879 (4) | |
N1' | 0.5139 (3) | −0.39505 (9) | −0.27022 (9) | 0.0511 (7) | |
N2' | 0.5869 (3) | −0.27488 (9) | −0.23757 (8) | 0.0472 (6) | |
N3' | 0.6404 (3) | −0.25842 (9) | −0.20137 (9) | 0.0507 (6) | |
C1' | 0.5788 (4) | −0.40452 (11) | −0.22871 (11) | 0.0528 (8) | |
C2' | 0.6031 (5) | −0.44834 (13) | −0.20820 (14) | 0.0653 (10) | |
C3' | 0.6675 (5) | −0.44766 (16) | −0.16640 (14) | 0.0741 (12) | |
C4' | 0.7066 (5) | −0.40496 (16) | −0.14559 (14) | 0.0719 (11) | |
C5' | 0.6843 (5) | −0.36184 (14) | −0.16613 (12) | 0.0609 (9) | |
C6' | 0.6189 (4) | −0.36101 (11) | −0.20842 (10) | 0.0491 (7) | |
C7' | 0.5757 (4) | −0.32428 (11) | −0.23947 (10) | 0.0468 (7) | |
C8' | 0.5123 (4) | −0.34649 (10) | −0.27674 (10) | 0.0458 (7) | |
C9' | 0.4609 (4) | −0.32430 (10) | −0.31831 (10) | 0.0447 (7) | |
C10' | 0.3596 (4) | −0.28421 (12) | −0.31830 (12) | 0.0522 (8) | |
C11' | 0.3218 (5) | −0.26138 (14) | −0.35717 (14) | 0.0663 (10) | |
C12' | 0.3827 (6) | −0.27861 (14) | −0.39624 (14) | 0.0703 (12) | |
C13' | 0.4798 (5) | −0.31888 (14) | −0.39711 (12) | 0.0620 (10) | |
C14' | 0.5191 (4) | −0.34177 (12) | −0.35835 (11) | 0.0518 (8) | |
C15' | 0.4314 (5) | −0.43090 (12) | −0.29704 (13) | 0.0713 (11) | |
C16' | 0.6409 (4) | −0.20735 (11) | −0.20031 (10) | 0.0465 (7) | |
C17' | 0.7387 (5) | −0.18588 (13) | −0.16900 (12) | 0.0568 (9) | |
C18' | 0.7441 (5) | −0.13657 (13) | −0.16497 (13) | 0.0601 (9) | |
C19' | 0.6469 (4) | −0.10930 (11) | −0.19184 (12) | 0.0555 (8) | |
C20' | 0.5462 (5) | −0.13012 (13) | −0.22257 (13) | 0.0618 (9) | |
C21' | 0.5426 (5) | −0.17913 (12) | −0.22727 (12) | 0.0583 (9) | |
H2' | 0.582 (4) | −0.4757 (12) | −0.2218 (11) | 0.062 (11)* | |
H3' | 0.682 (5) | −0.4772 (13) | −0.1515 (12) | 0.074 (11)* | |
H4' | 0.750 (4) | −0.4065 (11) | −0.1167 (11) | 0.056 (9)* | |
H5' | 0.714 (4) | −0.3323 (12) | −0.1524 (11) | 0.068 (11)* | |
H10' | 0.315 (4) | −0.2731 (11) | −0.2916 (11) | 0.063 (11)* | |
H11' | 0.257 (5) | −0.2344 (14) | −0.3561 (13) | 0.088 (14)* | |
H12' | 0.363 (4) | −0.2639 (12) | −0.4216 (12) | 0.064 (11)* | |
H13' | 0.521 (5) | −0.3314 (14) | −0.4237 (14) | 0.090 (14)* | |
H14' | 0.594 (5) | −0.3681 (13) | −0.3581 (12) | 0.075 (12)* | |
H15D | 0.4531 | −0.4621 | −0.2853 | 0.107* | |
H15E | 0.4724 | −0.4291 | −0.3266 | 0.107* | |
H15F | 0.3144 | −0.4251 | −0.2970 | 0.107* | |
H17' | 0.800 (4) | −0.2058 (11) | −0.1521 (11) | 0.057 (10)* | |
H18' | 0.812 (4) | −0.1220 (12) | −0.1438 (11) | 0.065 (10)* | |
H20' | 0.480 (4) | −0.1111 (12) | −0.2390 (11) | 0.062 (10)* | |
H21' | 0.466 (4) | −0.1943 (13) | −0.2464 (12) | 0.071 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0981 (8) | 0.0465 (5) | 0.0812 (7) | 0.0112 (5) | −0.0075 (6) | −0.0133 (4) |
N1 | 0.0479 (15) | 0.0360 (13) | 0.0532 (16) | −0.0008 (11) | −0.0030 (12) | −0.0015 (11) |
N2 | 0.0481 (15) | 0.0431 (14) | 0.0467 (15) | −0.0002 (11) | −0.0043 (12) | −0.0036 (11) |
N3 | 0.0571 (16) | 0.0449 (15) | 0.0491 (16) | −0.0008 (12) | 0.0016 (13) | −0.0038 (12) |
C1 | 0.0471 (17) | 0.0426 (16) | 0.0530 (19) | −0.0068 (13) | −0.0108 (15) | 0.0039 (14) |
C2 | 0.066 (2) | 0.0405 (18) | 0.066 (2) | −0.0034 (16) | −0.0122 (19) | 0.0065 (16) |
C3 | 0.073 (3) | 0.055 (2) | 0.070 (3) | −0.0129 (19) | −0.008 (2) | 0.018 (2) |
C4 | 0.062 (2) | 0.071 (3) | 0.055 (2) | −0.0165 (19) | −0.0039 (19) | 0.0145 (19) |
C5 | 0.0508 (19) | 0.058 (2) | 0.0462 (19) | −0.0088 (16) | −0.0055 (15) | −0.0012 (16) |
C6 | 0.0455 (17) | 0.0430 (16) | 0.0458 (17) | −0.0060 (13) | −0.0112 (14) | −0.0002 (13) |
C7 | 0.0452 (16) | 0.0360 (15) | 0.0462 (17) | −0.0024 (12) | −0.0040 (14) | −0.0015 (12) |
C8 | 0.0477 (17) | 0.0344 (14) | 0.0497 (18) | −0.0004 (12) | −0.0078 (14) | 0.0006 (13) |
C9 | 0.0473 (17) | 0.0413 (16) | 0.0484 (18) | 0.0030 (13) | 0.0012 (14) | 0.0018 (13) |
C10 | 0.057 (2) | 0.0474 (18) | 0.060 (2) | −0.0018 (15) | 0.0017 (18) | 0.0035 (16) |
C11 | 0.067 (2) | 0.057 (2) | 0.089 (3) | −0.0099 (19) | 0.010 (2) | 0.011 (2) |
C12 | 0.086 (3) | 0.078 (3) | 0.078 (3) | 0.000 (2) | 0.022 (3) | 0.023 (3) |
C13 | 0.100 (3) | 0.077 (3) | 0.057 (3) | 0.003 (2) | 0.017 (2) | 0.002 (2) |
C14 | 0.067 (2) | 0.050 (2) | 0.058 (2) | −0.0013 (17) | 0.0052 (18) | −0.0017 (17) |
C15 | 0.067 (2) | 0.0456 (18) | 0.066 (2) | 0.0081 (16) | −0.0031 (18) | −0.0094 (16) |
C16 | 0.0523 (18) | 0.0447 (17) | 0.0449 (17) | 0.0006 (14) | −0.0029 (14) | −0.0061 (13) |
C17 | 0.069 (2) | 0.0485 (19) | 0.054 (2) | 0.0008 (17) | 0.0059 (18) | −0.0012 (16) |
C18 | 0.068 (2) | 0.054 (2) | 0.053 (2) | 0.0072 (17) | 0.0055 (18) | −0.0117 (17) |
C19 | 0.060 (2) | 0.0437 (17) | 0.055 (2) | 0.0049 (15) | −0.0100 (17) | −0.0074 (14) |
C20 | 0.071 (2) | 0.0450 (18) | 0.055 (2) | −0.0032 (16) | −0.0009 (18) | −0.0014 (16) |
C21 | 0.072 (2) | 0.0463 (18) | 0.0446 (19) | 0.0005 (16) | 0.0040 (17) | −0.0061 (15) |
Cl1' | 0.0999 (8) | 0.0470 (5) | 0.1169 (9) | −0.0007 (5) | −0.0057 (7) | −0.0158 (5) |
N1' | 0.0654 (18) | 0.0368 (13) | 0.0510 (16) | 0.0037 (12) | 0.0001 (13) | −0.0004 (11) |
N2' | 0.0545 (16) | 0.0434 (14) | 0.0437 (15) | −0.0009 (12) | 0.0018 (12) | −0.0022 (11) |
N3' | 0.0595 (17) | 0.0459 (15) | 0.0466 (15) | 0.0014 (12) | −0.0017 (13) | −0.0017 (12) |
C1' | 0.060 (2) | 0.0488 (18) | 0.0499 (19) | 0.0103 (15) | 0.0045 (16) | 0.0033 (15) |
C2' | 0.083 (3) | 0.046 (2) | 0.067 (3) | 0.0140 (19) | 0.007 (2) | 0.0113 (18) |
C3' | 0.087 (3) | 0.067 (3) | 0.068 (3) | 0.020 (2) | 0.002 (2) | 0.026 (2) |
C4' | 0.080 (3) | 0.083 (3) | 0.053 (2) | 0.020 (2) | −0.003 (2) | 0.016 (2) |
C5' | 0.068 (2) | 0.064 (2) | 0.050 (2) | 0.0091 (19) | −0.0036 (18) | 0.0054 (18) |
C6' | 0.0521 (18) | 0.0483 (17) | 0.0469 (18) | 0.0067 (14) | 0.0037 (15) | 0.0053 (14) |
C7' | 0.0541 (19) | 0.0423 (16) | 0.0441 (17) | 0.0029 (14) | 0.0012 (14) | 0.0017 (13) |
C8' | 0.0545 (19) | 0.0371 (15) | 0.0459 (17) | 0.0043 (13) | 0.0033 (14) | −0.0021 (12) |
C9' | 0.0535 (18) | 0.0367 (15) | 0.0440 (17) | −0.0020 (13) | −0.0044 (14) | −0.0020 (12) |
C10' | 0.054 (2) | 0.0464 (18) | 0.056 (2) | 0.0009 (15) | −0.0029 (17) | −0.0041 (15) |
C11' | 0.070 (3) | 0.051 (2) | 0.078 (3) | 0.0044 (19) | −0.025 (2) | 0.0044 (19) |
C12' | 0.093 (3) | 0.061 (2) | 0.057 (2) | −0.016 (2) | −0.028 (2) | 0.0160 (19) |
C13' | 0.080 (3) | 0.060 (2) | 0.046 (2) | −0.0178 (19) | −0.0035 (19) | −0.0011 (17) |
C14' | 0.059 (2) | 0.0454 (18) | 0.0505 (19) | −0.0028 (15) | 0.0011 (16) | −0.0040 (15) |
C15' | 0.100 (3) | 0.0435 (19) | 0.070 (2) | −0.0067 (19) | −0.004 (2) | −0.0063 (17) |
C16' | 0.0512 (18) | 0.0443 (17) | 0.0439 (17) | −0.0013 (14) | 0.0017 (14) | −0.0017 (13) |
C17' | 0.064 (2) | 0.055 (2) | 0.052 (2) | 0.0011 (17) | −0.0143 (17) | −0.0037 (16) |
C18' | 0.063 (2) | 0.057 (2) | 0.060 (2) | −0.0057 (18) | −0.0119 (18) | −0.0134 (17) |
C19' | 0.057 (2) | 0.0458 (18) | 0.063 (2) | −0.0026 (15) | 0.0040 (17) | −0.0065 (16) |
C20' | 0.073 (2) | 0.050 (2) | 0.063 (2) | 0.0085 (18) | −0.014 (2) | 0.0000 (17) |
C21' | 0.068 (2) | 0.0478 (19) | 0.059 (2) | 0.0007 (17) | −0.0162 (19) | −0.0053 (16) |
Cl1—C19 | 1.735 (3) | Cl1'—C19' | 1.739 (3) |
N1—C8 | 1.375 (3) | N1'—C1' | 1.395 (4) |
N1—C1 | 1.391 (4) | N1'—C15' | 1.455 (4) |
N1—C15 | 1.462 (4) | N2'—C7' | 1.385 (4) |
N2—N3 | 1.277 (3) | N3'—N2' | 1.272 (3) |
N2—C7 | 1.385 (3) | N3'—C16' | 1.428 (4) |
N3—C16 | 1.422 (4) | C1'—C2' | 1.389 (4) |
C1—C2 | 1.395 (4) | C2'—H2' | 0.89 (3) |
C1—C6 | 1.406 (4) | C3'—C4' | 1.388 (6) |
C2—C3 | 1.374 (5) | C3'—H3' | 0.95 (4) |
C2—H2 | 0.94 (3) | C3'—C2' | 1.377 (6) |
C3—C4 | 1.386 (6) | C4'—H4' | 0.95 (3) |
C3—H3 | 0.95 (4) | C5'—C4' | 1.370 (5) |
C4—H4 | 0.90 (4) | C5'—H5' | 0.96 (3) |
C5—C4 | 1.379 (5) | C6'—C5' | 1.393 (5) |
C5—H5 | 0.99 (3) | C6'—C1' | 1.402 (4) |
C6—C5 | 1.402 (4) | C7'—C6' | 1.440 (4) |
C7—C8 | 1.391 (4) | C8'—N1' | 1.372 (4) |
C7—C6 | 1.440 (4) | C8'—C7' | 1.392 (4) |
C8—C9 | 1.470 (4) | C8'—C9' | 1.471 (4) |
C9—C14 | 1.384 (5) | C9'—C10' | 1.388 (4) |
C9—C10 | 1.401 (4) | C9'—C14' | 1.396 (4) |
C10—C11 | 1.374 (5) | C10'—C11' | 1.380 (5) |
C10—H10 | 0.94 (3) | C10'—H10' | 0.94 (3) |
C11—C12 | 1.375 (6) | C11'—H11' | 0.92 (4) |
C11—H11 | 0.99 (4) | C12'—C11' | 1.376 (6) |
C12—H12 | 1.00 (5) | C12'—H12' | 0.89 (4) |
C13—C12 | 1.368 (6) | C13'—C12' | 1.373 (6) |
C13—H13 | 0.95 (4) | C13'—H13' | 0.94 (4) |
C14—C13 | 1.379 (5) | C14'—C13' | 1.381 (5) |
C14—H14 | 0.92 (3) | C14'—H14' | 0.95 (4) |
C15—H15A | 0.9600 | C15'—H15D | 0.9600 |
C15—H15B | 0.9600 | C15'—H15E | 0.9600 |
C15—H15C | 0.9600 | C15'—H15F | 0.9600 |
C16—C17 | 1.385 (4) | C16'—C17' | 1.377 (4) |
C16—C21 | 1.390 (4) | C16'—C21' | 1.389 (4) |
C17—C18 | 1.388 (5) | C17'—H17' | 0.90 (3) |
C17—H17 | 0.96 (3) | C18'—C19' | 1.367 (5) |
C18—H18 | 0.96 (4) | C18'—C17' | 1.384 (5) |
C19—C18 | 1.372 (5) | C18'—H18' | 0.94 (3) |
C19—C20 | 1.380 (5) | C20'—C19' | 1.371 (5) |
C20—H20 | 0.98 (4) | C20'—C21' | 1.378 (5) |
C21—C20 | 1.379 (4) | C20'—H20' | 0.91 (3) |
C21—H21 | 0.95 (3) | C21'—H21' | 0.95 (4) |
C8—N1—C1 | 109.0 (3) | C8'—N1'—C1' | 108.8 (3) |
C8—N1—C15 | 127.9 (3) | C8'—N1'—C15' | 126.6 (3) |
C1—N1—C15 | 122.9 (3) | C1'—N1'—C15' | 123.5 (3) |
N3—N2—C7 | 114.3 (3) | N3'—N2'—C7' | 114.8 (3) |
N2—N3—C16 | 112.8 (3) | N2'—N3'—C16' | 112.5 (3) |
N1—C1—C2 | 128.5 (3) | C2'—C1'—N1' | 128.9 (3) |
N1—C1—C6 | 108.9 (3) | C2'—C1'—C6' | 122.2 (3) |
C2—C1—C6 | 122.6 (3) | N1'—C1'—C6' | 108.8 (3) |
C3—C2—C1 | 116.9 (4) | C3'—C2'—C1' | 117.2 (4) |
C3—C2—H2 | 124.5 (19) | C3'—C2'—H2' | 121 (2) |
C1—C2—H2 | 118.6 (19) | C1'—C2'—H2' | 121 (2) |
C2—C3—C4 | 121.4 (4) | C2'—C3'—C4' | 121.4 (4) |
C2—C3—H3 | 120 (2) | C2'—C3'—H3' | 118 (2) |
C4—C3—H3 | 119 (2) | C4'—C3'—H3' | 120 (2) |
C5—C4—C3 | 122.2 (4) | C5'—C4'—C3' | 121.2 (4) |
C5—C4—H4 | 114 (2) | C5'—C4'—H4' | 121 (2) |
C3—C4—H4 | 124 (2) | C3'—C4'—H4' | 118 (2) |
C4—C5—C6 | 117.9 (4) | C4'—C5'—C6' | 119.2 (4) |
C4—C5—H5 | 122.3 (19) | C4'—C5'—H5' | 122 (2) |
C6—C5—H5 | 119.7 (19) | C6'—C5'—H5' | 119 (2) |
C5—C6—C1 | 118.9 (3) | C5'—C6'—C1' | 118.8 (3) |
C5—C6—C7 | 135.6 (3) | C5'—C6'—C7' | 135.4 (3) |
C1—C6—C7 | 105.5 (3) | C1'—C6'—C7' | 105.8 (3) |
N2—C7—C8 | 120.7 (3) | N2'—C7'—C8' | 120.2 (3) |
N2—C7—C6 | 131.1 (3) | N2'—C7'—C6' | 131.9 (3) |
C8—C7—C6 | 108.2 (3) | C8'—C7'—C6' | 107.9 (3) |
N1—C8—C7 | 108.4 (3) | N1'—C8'—C7' | 108.7 (3) |
N1—C8—C9 | 122.8 (3) | N1'—C8'—C9' | 123.0 (3) |
C7—C8—C9 | 128.8 (3) | C7'—C8'—C9' | 128.2 (3) |
C14—C9—C10 | 118.6 (3) | C10'—C9'—C14' | 118.8 (3) |
C14—C9—C8 | 121.8 (3) | C10'—C9'—C8' | 120.5 (3) |
C10—C9—C8 | 119.6 (3) | C14'—C9'—C8' | 120.7 (3) |
C11—C10—C9 | 120.1 (4) | C11'—C10'—C9' | 120.3 (4) |
C11—C10—H10 | 122 (2) | C11'—C10'—H10' | 120 (2) |
C9—C10—H10 | 118 (2) | C9'—C10'—H10' | 119 (2) |
C10—C11—C12 | 120.6 (4) | C12'—C11'—C10' | 120.2 (4) |
C10—C11—H11 | 122 (2) | C12'—C11'—H11' | 121 (3) |
C12—C11—H11 | 117 (2) | C10'—C11'—H11' | 118 (3) |
C13—C12—C11 | 119.6 (4) | C13'—C12'—C11' | 120.5 (4) |
C13—C12—H12 | 123 (3) | C13'—C12'—H12' | 118 (2) |
C11—C12—H12 | 118 (3) | C11'—C12'—H12' | 122 (2) |
C12—C13—C14 | 120.8 (4) | C12'—C13'—C14' | 119.7 (4) |
C12—C13—H13 | 121 (3) | C12'—C13'—H13' | 122 (3) |
C14—C13—H13 | 118 (3) | C14'—C13'—H13' | 119 (3) |
C13—C14—C9 | 120.3 (4) | C13'—C14'—C9' | 120.6 (4) |
C13—C14—H14 | 121 (2) | C13'—C14'—H14' | 121 (2) |
C9—C14—H14 | 118 (2) | C9'—C14'—H14' | 119 (2) |
N1—C15—H15A | 109.5 | N1'—C15'—H15D | 109.5 |
N1—C15—H15B | 109.5 | N1'—C15'—H15E | 109.5 |
H15A—C15—H15B | 109.5 | H15D—C15'—H15E | 109.5 |
N1—C15—H15C | 109.5 | N1'—C15'—H15F | 109.5 |
H15A—C15—H15C | 109.5 | H15D—C15'—H15F | 109.5 |
H15B—C15—H15C | 109.5 | H15E—C15'—H15F | 109.5 |
C17—C16—C21 | 119.0 (3) | C17'—C16'—C21' | 119.4 (3) |
C17—C16—N3 | 116.0 (3) | C17'—C16'—N3' | 116.9 (3) |
C21—C16—N3 | 125.0 (3) | C21'—C16'—N3' | 123.6 (3) |
C16—C17—C18 | 120.9 (3) | C16'—C17'—C18' | 120.9 (3) |
C16—C17—H17 | 117 (2) | C16'—C17'—H17' | 116 (2) |
C18—C17—H17 | 122 (2) | C18'—C17'—H17' | 123 (2) |
C19—C18—C17 | 118.9 (3) | C19'—C18'—C17' | 118.9 (3) |
C19—C18—H18 | 123 (2) | C19'—C18'—H18' | 120 (2) |
C17—C18—H18 | 118 (2) | C17'—C18'—H18' | 121 (2) |
C18—C19—C20 | 121.3 (3) | C18'—C19'—C20' | 120.9 (3) |
C18—C19—Cl1 | 119.5 (3) | C18'—C19'—Cl1' | 119.7 (3) |
C20—C19—Cl1 | 119.2 (3) | C20'—C19'—Cl1' | 119.3 (3) |
C21—C20—C19 | 119.5 (3) | C19'—C20'—C21' | 120.4 (3) |
C21—C20—H20 | 124 (2) | C19'—C20'—H20' | 119 (2) |
C19—C20—H20 | 117 (2) | C21'—C20'—H20' | 121 (2) |
C20—C21—C16 | 120.5 (3) | C20'—C21'—C16' | 119.4 (3) |
C20—C21—H21 | 122 (2) | C20'—C21'—H21' | 121 (2) |
C16—C21—H21 | 117 (2) | C16'—C21'—H21' | 119 (2) |
C1—N1—C8—C7 | 0.0 (3) | C8'—N1'—C1'—C2' | 179.8 (4) |
C15—N1—C8—C7 | −173.7 (3) | C15'—N1'—C1'—C2' | 11.3 (6) |
C1—N1—C8—C9 | −178.8 (3) | C8'—N1'—C1'—C6' | 0.2 (4) |
C15—N1—C8—C9 | 7.4 (5) | C15'—N1'—C1'—C6' | −168.3 (3) |
C8—N1—C1—C2 | −178.4 (3) | N3'—N2'—C7'—C8' | 177.4 (3) |
C15—N1—C1—C2 | −4.3 (5) | N3'—N2'—C7'—C6' | −2.5 (5) |
C8—N1—C1—C6 | 0.5 (3) | C16'—N3'—N2'—C7' | −176.8 (3) |
C15—N1—C1—C6 | 174.6 (3) | N2'—N3'—C16'—C17' | −161.6 (3) |
N3—N2—C7—C8 | −174.3 (3) | N2'—N3'—C16'—C21' | 21.9 (4) |
N3—N2—C7—C6 | 4.0 (4) | N1'—C1'—C2'—C3' | −178.9 (4) |
C7—N2—N3—C16 | 175.4 (2) | C6'—C1'—C2'—C3' | 0.6 (6) |
N2—N3—C16—C17 | 178.3 (3) | C4'—C3'—C2'—C1' | −0.1 (6) |
N2—N3—C16—C21 | −5.3 (4) | C2'—C3'—C4'—C5' | −0.8 (7) |
N1—C1—C6—C5 | 179.4 (3) | C6'—C5'—C4'—C3' | 1.0 (6) |
C2—C1—C6—C5 | −1.7 (5) | C5'—C6'—C1'—C2' | −0.4 (5) |
N1—C1—C6—C7 | −0.8 (3) | C7'—C6'—C1'—C2' | −179.7 (3) |
C2—C1—C6—C7 | 178.2 (3) | C5'—C6'—C1'—N1' | 179.2 (3) |
N1—C1—C2—C3 | 178.2 (3) | C7'—C6'—C1'—N1' | −0.1 (4) |
C6—C1—C2—C3 | −0.6 (5) | C1'—C6'—C5'—C4' | −0.4 (5) |
C1—C2—C3—C4 | 2.1 (5) | C7'—C6'—C5'—C4' | 178.6 (4) |
C2—C3—C4—C5 | −1.4 (6) | N2'—C7'—C6'—C5' | 0.7 (7) |
C6—C5—C4—C3 | −0.9 (5) | C8'—C7'—C6'—C5' | −179.1 (4) |
C1—C6—C5—C4 | 2.4 (5) | N2'—C7'—C6'—C1' | 179.8 (3) |
C7—C6—C5—C4 | −177.5 (3) | C8'—C7'—C6'—C1' | −0.1 (4) |
N2—C7—C6—C5 | 2.2 (6) | C7'—C8'—N1'—C1' | −0.2 (4) |
C8—C7—C6—C5 | −179.4 (3) | C9'—C8'—N1'—C1' | 176.1 (3) |
N2—C7—C6—C1 | −177.7 (3) | C7'—C8'—N1'—C15' | 167.8 (3) |
C8—C7—C6—C1 | 0.8 (3) | C9'—C8'—N1'—C15' | −15.9 (5) |
N2—C7—C8—N1 | 178.1 (3) | N1'—C8'—C9'—C10' | 136.9 (3) |
C6—C7—C8—N1 | −0.5 (3) | C7'—C8'—C9'—C10' | −47.5 (5) |
N2—C7—C8—C9 | −3.1 (5) | N1'—C8'—C9'—C14' | −46.1 (5) |
C6—C7—C8—C9 | 178.2 (3) | C7'—C8'—C9'—C14' | 129.5 (4) |
N1—C8—C9—C14 | 42.5 (5) | N1'—C8'—C7'—N2' | −179.7 (3) |
C7—C8—C9—C14 | −136.1 (4) | C9'—C8'—C7'—N2' | 4.2 (5) |
N1—C8—C9—C10 | −138.0 (3) | N1'—C8'—C7'—C6' | 0.2 (4) |
C7—C8—C9—C10 | 43.4 (5) | C9'—C8'—C7'—C6' | −175.9 (3) |
C10—C9—C14—C13 | 0.8 (5) | C14'—C9'—C10'—C11' | −2.0 (5) |
C8—C9—C14—C13 | −179.7 (3) | C8'—C9'—C10'—C11' | 175.1 (3) |
C14—C9—C10—C11 | −0.2 (5) | C10'—C9'—C14'—C13' | 1.6 (5) |
C8—C9—C10—C11 | −179.7 (3) | C8'—C9'—C14'—C13' | −175.5 (3) |
C9—C10—C11—C12 | −0.4 (6) | C9'—C10'—C11'—C12' | 0.8 (6) |
C10—C11—C12—C13 | 0.3 (7) | C13'—C12'—C11'—C10' | 0.7 (6) |
C14—C13—C12—C11 | 0.4 (7) | C14'—C13'—C12'—C11' | −1.1 (6) |
C9—C14—C13—C12 | −0.9 (7) | C9'—C14'—C13'—C12' | −0.1 (5) |
C17—C16—C21—C20 | −1.0 (5) | C17'—C16'—C21'—C20' | 0.8 (5) |
N3—C16—C21—C20 | −177.2 (3) | N3'—C16'—C21'—C20' | 177.2 (3) |
C21—C16—C17—C18 | 0.8 (5) | C21'—C16'—C17'—C18' | −2.0 (5) |
N3—C16—C17—C18 | 177.4 (3) | N3'—C16'—C17'—C18' | −178.6 (3) |
C16—C17—C18—C19 | −0.4 (6) | C19'—C18'—C17'—C16' | 1.8 (6) |
C18—C19—C20—C21 | −0.3 (5) | C17'—C18'—C19'—C20' | −0.5 (6) |
Cl1—C19—C20—C21 | 178.8 (3) | C17'—C18'—C19'—Cl1' | 178.8 (3) |
C20—C19—C18—C17 | 0.1 (5) | C21'—C20'—C19'—C18' | −0.7 (6) |
Cl1—C19—C18—C17 | −179.0 (3) | C21'—C20'—C19'—Cl1' | −180.0 (3) |
C16—C21—C20—C19 | 0.7 (5) | C19'—C20'—C21'—C16' | 0.6 (6) |