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
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.005 Å
- R factor = 0.108
- wR factor = 0.205
- Data-to-parameter ratio = 19.0
checkCIF/PLATON results
No syntax errors found
Alert level C RFACG01_ALERT_3_C The value of the R factor is > 0.10 R factor given 0.108 PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT082_ALERT_2_C High R1 Value .................................. 0.11 PLAT128_ALERT_4_C Non-standard setting of Space group Pbca .... Pcab PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5 PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd. # 2 C21 H16 Cl N3
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 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 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
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) |
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