Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803021482/ob6307sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803021482/ob6307Isup2.hkl |
CCDC reference: 226932
Key indicators
- Single-crystal X-ray study
- T = 291 K
- Mean (C-C) = 0.003 Å
- R factor = 0.039
- wR factor = 0.087
- Data-to-parameter ratio = 12.9
checkCIF/PLATON results
No syntax errors found
Alert level C GOODF01_ALERT_2_C The least squares goodness of fit parameter lies outside the range 0.80 <> 2.00 Goodness of fit given = 0.795
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 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 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C23H16ClN3 | F(000) = 1536 |
Mr = 369.84 | Dx = 1.367 Mg m−3 |
Monoclinic, P21/c | Melting point = 452–453 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 7.789 (1) Å | Cell parameters from 35 reflections |
b = 17.777 (2) Å | θ = 2.9–14.9° |
c = 26.040 (3) Å | µ = 0.23 mm−1 |
β = 94.70 (1)° | T = 291 K |
V = 3593.7 (9) Å3 | Block, colorless |
Z = 8 | 0.54 × 0.48 × 0.34 mm |
Siemens P4 diffractometer | 3063 reflections with I > 2σ(I) |
Radiation source: normal-focus sealed tube | Rint = 0.011 |
Graphite monochromator | θmax = 25.0°, θmin = 1.4° |
ω scans | h = 0→9 |
Absorption correction: ψ scan (XSCANS; Siemens, 1994) | k = 0→21 |
Tmin = 0.882, Tmax = 0.926 | l = −30→30 |
7325 measured reflections | 3 standard reflections every 97 reflections |
6330 independent reflections | intensity decay: 1.9% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.087 | w = 1/[σ2(Fo2) + (0.0384P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.80 | (Δ/σ)max = 0.001 |
6330 reflections | Δρmax = 0.14 e Å−3 |
490 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Extinction correction: SHELXTL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0035 (2) |
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 | ||
Cl | 0.31998 (9) | 0.76302 (4) | 0.53087 (3) | 0.0816 (2) | |
N1 | 0.3554 (2) | 0.46802 (10) | 0.42845 (7) | 0.0593 (5) | |
N2 | 0.6123 (2) | 0.50260 (9) | 0.39244 (7) | 0.0472 (5) | |
N3 | 0.7484 (2) | 0.61308 (9) | 0.40530 (7) | 0.0508 (5) | |
C1 | 0.3512 (3) | 0.53833 (13) | 0.45174 (9) | 0.0553 (6) | |
C2 | 0.2160 (3) | 0.55456 (15) | 0.48200 (9) | 0.0698 (7) | |
H2 | 0.1315 | 0.5186 | 0.4861 | 0.084* | |
C3 | 0.2067 (3) | 0.62306 (15) | 0.50567 (9) | 0.0721 (8) | |
H3 | 0.1162 | 0.6335 | 0.5257 | 0.087* | |
C4 | 0.3333 (3) | 0.67714 (14) | 0.49964 (9) | 0.0622 (7) | |
C5 | 0.4667 (3) | 0.66296 (12) | 0.46996 (9) | 0.0570 (6) | |
H5 | 0.5500 | 0.6994 | 0.4659 | 0.068* | |
C6 | 0.4761 (3) | 0.59334 (12) | 0.44600 (8) | 0.0503 (6) | |
C7 | 0.6132 (3) | 0.57348 (12) | 0.41533 (8) | 0.0486 (6) | |
C8 | 0.4797 (3) | 0.45110 (12) | 0.40057 (9) | 0.0535 (6) | |
C9 | 0.7638 (3) | 0.49878 (11) | 0.36624 (8) | 0.0456 (6) | |
C10 | 0.8428 (3) | 0.56719 (11) | 0.37502 (8) | 0.0461 (6) | |
C11 | 0.8166 (3) | 0.43284 (11) | 0.33675 (8) | 0.0467 (6) | |
C12 | 0.7370 (3) | 0.41576 (12) | 0.28860 (9) | 0.0577 (6) | |
H12 | 0.6484 | 0.4463 | 0.2744 | 0.069* | |
C13 | 0.7875 (3) | 0.35397 (13) | 0.26133 (9) | 0.0662 (7) | |
H13 | 0.7325 | 0.3431 | 0.2291 | 0.079* | |
C14 | 0.9183 (4) | 0.30872 (13) | 0.28162 (10) | 0.0689 (8) | |
H14 | 0.9504 | 0.2664 | 0.2637 | 0.083* | |
C15 | 1.0020 (3) | 0.32625 (12) | 0.32867 (10) | 0.0648 (7) | |
H15 | 1.0932 | 0.2964 | 0.3420 | 0.078* | |
C16 | 0.9519 (3) | 0.38774 (12) | 0.35632 (8) | 0.0545 (6) | |
H16 | 1.0092 | 0.3989 | 0.3882 | 0.065* | |
C17 | 1.0036 (3) | 0.59804 (11) | 0.35697 (8) | 0.0456 (6) | |
C18 | 1.0557 (3) | 0.66954 (11) | 0.37360 (8) | 0.0542 (6) | |
H18 | 0.9905 | 0.6954 | 0.3962 | 0.065* | |
C19 | 1.2016 (3) | 0.70281 (13) | 0.35730 (9) | 0.0650 (7) | |
H19 | 1.2331 | 0.7508 | 0.3687 | 0.078* | |
C20 | 1.3003 (3) | 0.66521 (14) | 0.32439 (10) | 0.0696 (8) | |
H20 | 1.3992 | 0.6875 | 0.3136 | 0.084* | |
C21 | 1.2523 (3) | 0.59447 (14) | 0.30736 (9) | 0.0682 (7) | |
H21 | 1.3191 | 0.5689 | 0.2850 | 0.082* | |
C22 | 1.1049 (3) | 0.56114 (12) | 0.32335 (8) | 0.0577 (7) | |
H22 | 1.0734 | 0.5134 | 0.3114 | 0.069* | |
C23 | 0.4808 (3) | 0.37564 (12) | 0.37614 (9) | 0.0691 (7) | |
H23A | 0.3985 | 0.3438 | 0.3910 | 0.083* | |
H23B | 0.5936 | 0.3540 | 0.3818 | 0.083* | |
H23C | 0.4508 | 0.3804 | 0.3398 | 0.083* | |
Cl' | −0.17754 (10) | 0.75994 (4) | 0.53180 (3) | 0.0955 (3) | |
N1' | −0.1547 (2) | 1.04812 (11) | 0.41982 (8) | 0.0639 (6) | |
N2' | 0.1019 (2) | 1.01240 (9) | 0.38499 (7) | 0.0482 (5) | |
N3' | 0.2419 (2) | 0.90328 (9) | 0.40045 (7) | 0.0504 (5) | |
C1' | −0.1554 (3) | 0.97976 (14) | 0.44558 (9) | 0.0571 (6) | |
C2' | −0.2881 (3) | 0.96504 (16) | 0.47769 (10) | 0.0762 (8) | |
H2' | −0.3727 | 1.0011 | 0.4814 | 0.091* | |
C3' | −0.2937 (3) | 0.89830 (17) | 0.50352 (10) | 0.0796 (8) | |
H3' | −0.3818 | 0.8891 | 0.5248 | 0.096* | |
C4' | −0.1681 (3) | 0.84436 (14) | 0.49802 (9) | 0.0659 (7) | |
C5' | −0.0365 (3) | 0.85649 (13) | 0.46739 (8) | 0.0582 (6) | |
H5' | 0.0476 | 0.8200 | 0.4642 | 0.070* | |
C6' | −0.0307 (3) | 0.92476 (13) | 0.44098 (8) | 0.0513 (6) | |
C7' | 0.1057 (3) | 0.94273 (12) | 0.40925 (8) | 0.0470 (6) | |
C8' | −0.0326 (3) | 1.06344 (12) | 0.39091 (9) | 0.0572 (6) | |
C9' | 0.2530 (3) | 1.01581 (11) | 0.35889 (8) | 0.0479 (6) | |
C10' | 0.3350 (3) | 0.94790 (11) | 0.36922 (8) | 0.0459 (6) | |
C11' | 0.3074 (3) | 1.08175 (11) | 0.32978 (8) | 0.0469 (6) | |
C12' | 0.2349 (3) | 1.09708 (12) | 0.28028 (9) | 0.0583 (7) | |
H12' | 0.1524 | 1.0647 | 0.2647 | 0.070* | |
C13' | 0.2843 (3) | 1.15997 (13) | 0.25407 (9) | 0.0670 (7) | |
H13' | 0.2340 | 1.1701 | 0.2212 | 0.080* | |
C14' | 0.4069 (3) | 1.20746 (13) | 0.27636 (10) | 0.0648 (7) | |
H14' | 0.4378 | 1.2504 | 0.2589 | 0.078* | |
C15' | 0.4842 (3) | 1.19182 (12) | 0.32420 (10) | 0.0632 (7) | |
H15' | 0.5703 | 1.2233 | 0.3388 | 0.076* | |
C16' | 0.4348 (3) | 1.12938 (12) | 0.35101 (9) | 0.0542 (6) | |
H16' | 0.4877 | 1.1193 | 0.3836 | 0.065* | |
C17' | 0.4972 (3) | 0.91750 (11) | 0.35208 (8) | 0.0459 (6) | |
C18' | 0.5534 (3) | 0.84765 (12) | 0.37075 (8) | 0.0530 (6) | |
H18' | 0.4893 | 0.8225 | 0.3940 | 0.064* | |
C19' | 0.7006 (3) | 0.81491 (13) | 0.35578 (9) | 0.0612 (7) | |
H19' | 0.7344 | 0.7679 | 0.3686 | 0.073* | |
C20' | 0.7987 (3) | 0.85157 (14) | 0.32182 (9) | 0.0664 (7) | |
H20' | 0.8992 | 0.8298 | 0.3118 | 0.080* | |
C21' | 0.7461 (3) | 0.92047 (14) | 0.30308 (9) | 0.0657 (7) | |
H21' | 0.8118 | 0.9455 | 0.2802 | 0.079* | |
C22' | 0.5968 (3) | 0.95348 (12) | 0.31771 (8) | 0.0561 (6) | |
H22' | 0.5629 | 1.0002 | 0.3044 | 0.067* | |
C23' | −0.0385 (3) | 1.13622 (12) | 0.36268 (10) | 0.0862 (9) | |
H23D | −0.0674 | 1.1272 | 0.3267 | 0.103* | |
H23E | 0.0721 | 1.1602 | 0.3673 | 0.103* | |
H23F | −0.1239 | 1.1682 | 0.3758 | 0.103* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.0740 (6) | 0.0977 (5) | 0.0741 (5) | 0.0230 (4) | 0.0122 (4) | −0.0156 (4) |
N1 | 0.0458 (14) | 0.0673 (13) | 0.0653 (14) | −0.0038 (10) | 0.0083 (11) | 0.0091 (11) |
N2 | 0.0399 (13) | 0.0474 (11) | 0.0547 (12) | −0.0008 (9) | 0.0062 (10) | 0.0049 (9) |
N3 | 0.0457 (13) | 0.0493 (11) | 0.0585 (12) | 0.0013 (10) | 0.0114 (10) | 0.0004 (9) |
C1 | 0.0477 (17) | 0.0670 (16) | 0.0514 (15) | 0.0014 (13) | 0.0060 (13) | 0.0075 (12) |
C2 | 0.0515 (18) | 0.089 (2) | 0.0718 (19) | −0.0037 (14) | 0.0199 (15) | 0.0097 (15) |
C3 | 0.059 (2) | 0.100 (2) | 0.0590 (18) | 0.0156 (16) | 0.0172 (15) | 0.0035 (16) |
C4 | 0.0541 (19) | 0.0819 (18) | 0.0508 (16) | 0.0144 (14) | 0.0050 (14) | 0.0004 (13) |
C5 | 0.0507 (18) | 0.0672 (16) | 0.0536 (15) | 0.0065 (12) | 0.0081 (13) | 0.0029 (12) |
C6 | 0.0433 (16) | 0.0593 (15) | 0.0486 (14) | 0.0037 (12) | 0.0067 (12) | 0.0063 (12) |
C7 | 0.0473 (17) | 0.0473 (14) | 0.0514 (14) | 0.0014 (12) | 0.0051 (12) | 0.0064 (11) |
C8 | 0.0478 (17) | 0.0519 (14) | 0.0595 (15) | −0.0069 (12) | −0.0024 (13) | 0.0099 (12) |
C9 | 0.0406 (15) | 0.0500 (14) | 0.0463 (13) | 0.0029 (11) | 0.0043 (11) | 0.0035 (11) |
C10 | 0.0426 (15) | 0.0451 (13) | 0.0509 (14) | 0.0026 (11) | 0.0062 (12) | 0.0015 (11) |
C11 | 0.0494 (15) | 0.0415 (12) | 0.0492 (14) | −0.0014 (11) | 0.0047 (12) | 0.0026 (11) |
C12 | 0.0644 (18) | 0.0512 (14) | 0.0568 (16) | 0.0021 (12) | 0.0003 (14) | 0.0050 (12) |
C13 | 0.085 (2) | 0.0614 (16) | 0.0521 (16) | −0.0100 (15) | 0.0066 (15) | −0.0036 (13) |
C14 | 0.089 (2) | 0.0484 (15) | 0.072 (2) | 0.0009 (15) | 0.0265 (17) | −0.0030 (14) |
C15 | 0.0634 (19) | 0.0525 (16) | 0.0798 (19) | 0.0114 (13) | 0.0147 (16) | 0.0081 (14) |
C16 | 0.0539 (16) | 0.0553 (14) | 0.0543 (15) | 0.0022 (12) | 0.0050 (13) | 0.0060 (12) |
C17 | 0.0416 (15) | 0.0476 (13) | 0.0475 (14) | 0.0012 (11) | 0.0036 (12) | 0.0051 (11) |
C18 | 0.0456 (16) | 0.0513 (14) | 0.0656 (16) | 0.0014 (12) | 0.0044 (13) | 0.0007 (12) |
C19 | 0.0571 (19) | 0.0591 (15) | 0.0787 (19) | −0.0114 (14) | 0.0052 (15) | 0.0041 (14) |
C20 | 0.0555 (19) | 0.0782 (19) | 0.0767 (19) | −0.0143 (15) | 0.0144 (16) | 0.0144 (15) |
C21 | 0.064 (2) | 0.0776 (18) | 0.0662 (18) | −0.0037 (15) | 0.0251 (15) | 0.0000 (14) |
C22 | 0.0563 (18) | 0.0591 (15) | 0.0590 (16) | −0.0033 (13) | 0.0131 (14) | −0.0008 (12) |
C23 | 0.0607 (18) | 0.0618 (16) | 0.0864 (19) | −0.0165 (13) | 0.0159 (15) | 0.0018 (14) |
Cl' | 0.0724 (6) | 0.1373 (7) | 0.0779 (5) | −0.0182 (5) | 0.0125 (4) | 0.0366 (5) |
N1' | 0.0484 (15) | 0.0665 (14) | 0.0782 (15) | −0.0006 (11) | 0.0143 (12) | −0.0167 (11) |
N2' | 0.0398 (13) | 0.0492 (11) | 0.0564 (12) | −0.0022 (9) | 0.0078 (10) | −0.0081 (9) |
N3' | 0.0432 (13) | 0.0534 (11) | 0.0555 (12) | −0.0005 (10) | 0.0101 (10) | −0.0005 (9) |
C1' | 0.0441 (17) | 0.0729 (17) | 0.0549 (15) | −0.0067 (13) | 0.0087 (13) | −0.0148 (13) |
C2' | 0.0522 (19) | 0.103 (2) | 0.076 (2) | 0.0058 (15) | 0.0205 (16) | −0.0141 (17) |
C3' | 0.0525 (19) | 0.125 (3) | 0.0647 (19) | −0.0080 (18) | 0.0235 (15) | 0.0013 (18) |
C4' | 0.0513 (19) | 0.098 (2) | 0.0482 (16) | −0.0121 (15) | 0.0048 (14) | 0.0064 (14) |
C5' | 0.0450 (17) | 0.0797 (17) | 0.0502 (15) | −0.0065 (13) | 0.0046 (13) | 0.0011 (13) |
C6' | 0.0403 (16) | 0.0650 (15) | 0.0491 (14) | −0.0061 (12) | 0.0064 (12) | −0.0084 (12) |
C7' | 0.0372 (15) | 0.0536 (14) | 0.0507 (14) | −0.0048 (11) | 0.0064 (12) | −0.0072 (11) |
C8' | 0.0448 (17) | 0.0545 (15) | 0.0728 (18) | 0.0003 (12) | 0.0085 (13) | −0.0159 (13) |
C9' | 0.0409 (15) | 0.0505 (14) | 0.0523 (14) | −0.0016 (11) | 0.0037 (12) | −0.0071 (11) |
C10' | 0.0405 (15) | 0.0498 (13) | 0.0479 (14) | −0.0034 (11) | 0.0071 (11) | −0.0058 (11) |
C11' | 0.0456 (15) | 0.0441 (13) | 0.0517 (15) | 0.0020 (11) | 0.0083 (12) | −0.0053 (11) |
C12' | 0.0643 (18) | 0.0497 (14) | 0.0600 (16) | −0.0019 (12) | −0.0013 (14) | −0.0071 (12) |
C13' | 0.079 (2) | 0.0624 (16) | 0.0588 (17) | 0.0043 (15) | −0.0002 (15) | 0.0006 (13) |
C14' | 0.076 (2) | 0.0499 (15) | 0.0716 (18) | 0.0016 (14) | 0.0222 (15) | 0.0039 (14) |
C15' | 0.0620 (18) | 0.0575 (16) | 0.0709 (18) | −0.0146 (13) | 0.0104 (15) | −0.0079 (14) |
C16' | 0.0529 (17) | 0.0556 (14) | 0.0539 (15) | −0.0071 (12) | 0.0032 (13) | −0.0060 (12) |
C17' | 0.0445 (15) | 0.0484 (13) | 0.0446 (13) | −0.0018 (11) | 0.0032 (12) | −0.0058 (11) |
C18' | 0.0452 (16) | 0.0539 (14) | 0.0600 (16) | −0.0041 (12) | 0.0060 (13) | −0.0031 (12) |
C19' | 0.0554 (19) | 0.0564 (15) | 0.0713 (18) | 0.0078 (13) | 0.0026 (15) | −0.0043 (13) |
C20' | 0.0593 (19) | 0.0711 (18) | 0.0698 (18) | 0.0142 (14) | 0.0112 (15) | −0.0136 (14) |
C21' | 0.0578 (19) | 0.0822 (18) | 0.0603 (17) | −0.0007 (14) | 0.0243 (14) | −0.0035 (14) |
C22' | 0.0564 (18) | 0.0576 (15) | 0.0555 (15) | 0.0029 (13) | 0.0125 (13) | 0.0006 (12) |
C23' | 0.070 (2) | 0.0565 (16) | 0.135 (3) | 0.0129 (14) | 0.0262 (18) | −0.0038 (16) |
Cl—C4 | 1.737 (2) | Cl'—C4' | 1.744 (2) |
N1—C8 | 1.292 (3) | N1'—C8' | 1.290 (3) |
N1—C1 | 1.391 (3) | N1'—C1' | 1.388 (3) |
N2—C7 | 1.394 (2) | N2'—C7' | 1.390 (2) |
N2—C8 | 1.409 (3) | N2'—C8' | 1.404 (3) |
N2—C9 | 1.413 (2) | N2'—C9' | 1.408 (3) |
N3—C7 | 1.311 (2) | N3'—C7' | 1.307 (2) |
N3—C10 | 1.387 (2) | N3'—C10' | 1.383 (2) |
C1—C6 | 1.396 (3) | C1'—C6' | 1.390 (3) |
C1—C2 | 1.396 (3) | C1'—C2' | 1.406 (3) |
C2—C3 | 1.369 (3) | C2'—C3' | 1.366 (3) |
C2—H2 | 0.9300 | C2'—H2' | 0.9300 |
C3—C4 | 1.395 (3) | C3'—C4' | 1.386 (3) |
C3—H3 | 0.9300 | C3'—H3' | 0.9300 |
C4—C5 | 1.368 (3) | C4'—C5' | 1.367 (3) |
C5—C6 | 1.391 (3) | C5'—C6' | 1.398 (3) |
C5—H5 | 0.9300 | C5'—H5' | 0.9300 |
C6—C7 | 1.429 (3) | C6'—C7' | 1.435 (3) |
C8—C23 | 1.485 (3) | C8'—C23' | 1.487 (3) |
C9—C10 | 1.374 (3) | C9'—C10' | 1.382 (3) |
C9—C11 | 1.478 (3) | C9'—C11' | 1.477 (3) |
C10—C17 | 1.478 (3) | C10'—C17' | 1.476 (3) |
C11—C12 | 1.386 (3) | C11'—C16' | 1.385 (3) |
C11—C16 | 1.388 (3) | C11'—C12' | 1.391 (3) |
C12—C13 | 1.382 (3) | C12'—C13' | 1.381 (3) |
C12—H12 | 0.9300 | C12'—H12' | 0.9300 |
C13—C14 | 1.370 (3) | C13'—C14' | 1.368 (3) |
C13—H13 | 0.9300 | C13'—H13' | 0.9300 |
C14—C15 | 1.376 (3) | C14'—C15' | 1.367 (3) |
C14—H14 | 0.9300 | C14'—H14' | 0.9300 |
C15—C16 | 1.383 (3) | C15'—C16' | 1.382 (3) |
C15—H15 | 0.9300 | C15'—H15' | 0.9300 |
C16—H16 | 0.9300 | C16'—H16' | 0.9300 |
C17—C22 | 1.390 (3) | C17'—C22' | 1.388 (3) |
C17—C18 | 1.393 (3) | C17'—C18' | 1.391 (3) |
C18—C19 | 1.379 (3) | C18'—C19' | 1.371 (3) |
C18—H18 | 0.9300 | C18'—H18' | 0.9300 |
C19—C20 | 1.371 (3) | C19'—C20' | 1.379 (3) |
C19—H19 | 0.9300 | C19'—H19' | 0.9300 |
C20—C21 | 1.375 (3) | C20'—C21' | 1.369 (3) |
C20—H20 | 0.9300 | C20'—H20' | 0.9300 |
C21—C22 | 1.386 (3) | C21'—C22' | 1.384 (3) |
C21—H21 | 0.9300 | C21'—H21' | 0.9300 |
C22—H22 | 0.9300 | C22'—H22' | 0.9300 |
C23—H23A | 0.9600 | C23'—H23D | 0.9600 |
C23—H23B | 0.9600 | C23'—H23E | 0.9600 |
C23—H23C | 0.9600 | C23'—H23F | 0.9600 |
C8—N1—C1 | 120.0 (2) | C8'—N1'—C1' | 120.0 (2) |
C7—N2—C8 | 120.07 (19) | C7'—N2'—C8' | 120.98 (19) |
C7—N2—C9 | 105.96 (17) | C7'—N2'—C9' | 105.66 (17) |
C8—N2—C9 | 133.89 (19) | C8'—N2'—C9' | 133.32 (19) |
C7—N3—C10 | 105.64 (18) | C7'—N3'—C10' | 105.52 (18) |
N1—C1—C6 | 122.8 (2) | N1'—C1'—C6' | 122.9 (2) |
N1—C1—C2 | 118.5 (2) | N1'—C1'—C2' | 118.9 (2) |
C6—C1—C2 | 118.7 (2) | C6'—C1'—C2' | 118.2 (2) |
C3—C2—C1 | 120.5 (2) | C3'—C2'—C1' | 120.6 (3) |
C3—C2—H2 | 119.7 | C3'—C2'—H2' | 119.7 |
C1—C2—H2 | 119.7 | C1'—C2'—H2' | 119.7 |
C2—C3—C4 | 119.9 (3) | C2'—C3'—C4' | 119.9 (3) |
C2—C3—H3 | 120.0 | C2'—C3'—H3' | 120.1 |
C4—C3—H3 | 120.0 | C4'—C3'—H3' | 120.1 |
C5—C4—C3 | 120.9 (2) | C5'—C4'—C3' | 121.4 (2) |
C5—C4—Cl | 120.2 (2) | C5'—C4'—Cl' | 119.6 (2) |
C3—C4—Cl | 118.9 (2) | C3'—C4'—Cl' | 118.9 (2) |
C4—C5—C6 | 119.2 (2) | C4'—C5'—C6' | 118.7 (2) |
C4—C5—H5 | 120.4 | C4'—C5'—H5' | 120.7 |
C6—C5—H5 | 120.4 | C6'—C5'—H5' | 120.7 |
C5—C6—C1 | 120.8 (2) | C1'—C6'—C5' | 121.2 (2) |
C5—C6—C7 | 122.7 (2) | C1'—C6'—C7' | 116.7 (2) |
C1—C6—C7 | 116.5 (2) | C5'—C6'—C7' | 122.1 (2) |
N3—C7—N2 | 112.1 (2) | N3'—C7'—N2' | 112.71 (19) |
N3—C7—C6 | 128.9 (2) | N3'—C7'—C6' | 129.2 (2) |
N2—C7—C6 | 119.0 (2) | N2'—C7'—C6' | 118.1 (2) |
N1—C8—N2 | 121.7 (2) | N1'—C8'—N2' | 121.3 (2) |
N1—C8—C23 | 118.8 (2) | N1'—C8'—C23' | 118.5 (2) |
N2—C8—C23 | 119.5 (2) | N2'—C8'—C23' | 120.1 (2) |
C10—C9—N2 | 104.94 (18) | C10'—C9'—N2' | 105.08 (18) |
C10—C9—C11 | 130.5 (2) | C10'—C9'—C11' | 130.2 (2) |
N2—C9—C11 | 124.60 (19) | N2'—C9'—C11' | 124.65 (19) |
C9—C10—N3 | 111.4 (2) | C9'—C10'—N3' | 111.0 (2) |
C9—C10—C17 | 130.9 (2) | C9'—C10'—C17' | 130.9 (2) |
N3—C10—C17 | 117.71 (19) | N3'—C10'—C17' | 118.09 (19) |
C12—C11—C16 | 118.4 (2) | C16'—C11'—C12' | 118.3 (2) |
C12—C11—C9 | 121.4 (2) | C16'—C11'—C9' | 120.5 (2) |
C16—C11—C9 | 120.2 (2) | C12'—C11'—C9' | 121.3 (2) |
C13—C12—C11 | 120.9 (2) | C13'—C12'—C11' | 120.5 (2) |
C13—C12—H12 | 119.5 | C13'—C12'—H12' | 119.7 |
C11—C12—H12 | 119.5 | C11'—C12'—H12' | 119.7 |
C14—C13—C12 | 120.2 (2) | C14'—C13'—C12' | 120.2 (2) |
C14—C13—H13 | 119.9 | C14'—C13'—H13' | 119.9 |
C12—C13—H13 | 119.9 | C12'—C13'—H13' | 119.9 |
C13—C14—C15 | 119.6 (2) | C15'—C14'—C13' | 120.1 (2) |
C13—C14—H14 | 120.2 | C15'—C14'—H14' | 120.0 |
C15—C14—H14 | 120.2 | C13'—C14'—H14' | 120.0 |
C14—C15—C16 | 120.6 (2) | C14'—C15'—C16' | 120.2 (2) |
C14—C15—H15 | 119.7 | C14'—C15'—H15' | 119.9 |
C16—C15—H15 | 119.7 | C16'—C15'—H15' | 119.9 |
C15—C16—C11 | 120.3 (2) | C15'—C16'—C11' | 120.6 (2) |
C15—C16—H16 | 119.9 | C15'—C16'—H16' | 119.7 |
C11—C16—H16 | 119.9 | C11'—C16'—H16' | 119.7 |
C22—C17—C18 | 117.4 (2) | C22'—C17'—C18' | 117.4 (2) |
C22—C17—C10 | 124.4 (2) | C22'—C17'—C10' | 124.3 (2) |
C18—C17—C10 | 118.2 (2) | C18'—C17'—C10' | 118.3 (2) |
C19—C18—C17 | 121.5 (2) | C19'—C18'—C17' | 121.8 (2) |
C19—C18—H18 | 119.3 | C19'—C18'—H18' | 119.1 |
C17—C18—H18 | 119.3 | C17'—C18'—H18' | 119.1 |
C20—C19—C18 | 120.1 (2) | C18'—C19'—C20' | 120.1 (2) |
C20—C19—H19 | 119.9 | C18'—C19'—H19' | 119.9 |
C18—C19—H19 | 119.9 | C20'—C19'—H19' | 119.9 |
C19—C20—C21 | 119.8 (2) | C21'—C20'—C19' | 119.1 (2) |
C19—C20—H20 | 120.1 | C21'—C20'—H20' | 120.4 |
C21—C20—H20 | 120.1 | C19'—C20'—H20' | 120.4 |
C20—C21—C22 | 120.2 (2) | C20'—C21'—C22' | 121.0 (2) |
C20—C21—H21 | 119.9 | C20'—C21'—H21' | 119.5 |
C22—C21—H21 | 119.9 | C22'—C21'—H21' | 119.5 |
C21—C22—C17 | 121.0 (2) | C21'—C22'—C17' | 120.6 (2) |
C21—C22—H22 | 119.5 | C21'—C22'—H22' | 119.7 |
C17—C22—H22 | 119.5 | C17'—C22'—H22' | 119.7 |
C8—C23—H23A | 109.5 | C8'—C23'—H23D | 109.5 |
C8—C23—H23B | 109.5 | C8'—C23'—H23E | 109.5 |
H23A—C23—H23B | 109.5 | H23D—C23'—H23E | 109.5 |
C8—C23—H23C | 109.5 | C8'—C23'—H23F | 109.5 |
H23A—C23—H23C | 109.5 | H23D—C23'—H23F | 109.5 |
H23B—C23—H23C | 109.5 | H23E—C23'—H23F | 109.5 |
C8—N1—C1—C6 | 0.8 (3) | C8'—N1'—C1'—C6' | −1.5 (3) |
C8—N1—C1—C2 | −179.4 (2) | C8'—N1'—C1'—C2' | 178.7 (2) |
N1—C1—C2—C3 | 180.0 (2) | N1'—C1'—C2'—C3' | 179.7 (2) |
C6—C1—C2—C3 | −0.2 (4) | C6'—C1'—C2'—C3' | −0.1 (4) |
C1—C2—C3—C4 | −0.1 (4) | C1'—C2'—C3'—C4' | −0.2 (4) |
C2—C3—C4—C5 | 0.5 (4) | C2'—C3'—C4'—C5' | 0.5 (4) |
C2—C3—C4—Cl | −179.07 (18) | C2'—C3'—C4'—Cl' | 179.5 (2) |
C3—C4—C5—C6 | −0.6 (4) | C3'—C4'—C5'—C6' | −0.5 (4) |
Cl—C4—C5—C6 | 178.97 (17) | Cl'—C4'—C5'—C6' | −179.52 (17) |
C4—C5—C6—C1 | 0.3 (3) | N1'—C1'—C6'—C5' | −179.7 (2) |
C4—C5—C6—C7 | −178.6 (2) | C2'—C1'—C6'—C5' | 0.1 (3) |
N1—C1—C6—C5 | 179.9 (2) | N1'—C1'—C6'—C7' | 2.2 (3) |
C2—C1—C6—C5 | 0.1 (3) | C2'—C1'—C6'—C7' | −178.0 (2) |
N1—C1—C6—C7 | −1.2 (3) | C4'—C5'—C6'—C1' | 0.2 (3) |
C2—C1—C6—C7 | 179.0 (2) | C4'—C5'—C6'—C7' | 178.2 (2) |
C10—N3—C7—N2 | −0.6 (2) | C10'—N3'—C7'—N2' | 0.3 (2) |
C10—N3—C7—C6 | 178.4 (2) | C10'—N3'—C7'—C6' | −177.2 (2) |
C8—N2—C7—N3 | 177.70 (18) | C8'—N2'—C7'—N3' | −178.53 (19) |
C9—N2—C7—N3 | 0.6 (2) | C9'—N2'—C7'—N3' | −0.5 (2) |
C8—N2—C7—C6 | −1.4 (3) | C8'—N2'—C7'—C6' | −0.7 (3) |
C9—N2—C7—C6 | −178.47 (19) | C9'—N2'—C7'—C6' | 177.42 (18) |
C5—C6—C7—N3 | 1.4 (4) | C1'—C6'—C7'—N3' | 176.4 (2) |
C1—C6—C7—N3 | −177.5 (2) | C5'—C6'—C7'—N3' | −1.7 (4) |
C5—C6—C7—N2 | −179.66 (19) | C1'—C6'—C7'—N2' | −1.1 (3) |
C1—C6—C7—N2 | 1.4 (3) | C5'—C6'—C7'—N2' | −179.17 (19) |
C1—N1—C8—N2 | −0.6 (3) | C1'—N1'—C8'—N2' | −0.4 (3) |
C1—N1—C8—C23 | −179.95 (19) | C1'—N1'—C8'—C23' | 178.2 (2) |
C7—N2—C8—N1 | 1.0 (3) | C7'—N2'—C8'—N1' | 1.5 (3) |
C9—N2—C8—N1 | 177.1 (2) | C9'—N2'—C8'—N1' | −176.0 (2) |
C7—N2—C8—C23 | −179.72 (19) | C7'—N2'—C8'—C23' | −177.2 (2) |
C9—N2—C8—C23 | −3.6 (3) | C9'—N2'—C8'—C23' | 5.4 (4) |
C7—N2—C9—C10 | −0.4 (2) | C7'—N2'—C9'—C10' | 0.4 (2) |
C8—N2—C9—C10 | −176.9 (2) | C8'—N2'—C9'—C10' | 178.1 (2) |
C7—N2—C9—C11 | 179.39 (19) | C7'—N2'—C9'—C11' | −176.76 (19) |
C8—N2—C9—C11 | 2.9 (4) | C8'—N2'—C9'—C11' | 1.0 (4) |
N2—C9—C10—N3 | 0.1 (2) | N2'—C9'—C10'—N3' | −0.2 (2) |
C11—C9—C10—N3 | −179.7 (2) | C11'—C9'—C10'—N3' | 176.7 (2) |
N2—C9—C10—C17 | −178.5 (2) | N2'—C9'—C10'—C17' | 178.9 (2) |
C11—C9—C10—C17 | 1.7 (4) | C11'—C9'—C10'—C17' | −4.2 (4) |
C7—N3—C10—C9 | 0.3 (2) | C7'—N3'—C10'—C9' | −0.1 (2) |
C7—N3—C10—C17 | 179.11 (18) | C7'—N3'—C10'—C17' | −179.28 (18) |
C10—C9—C11—C12 | −104.9 (3) | C10'—C9'—C11'—C16' | −74.5 (3) |
N2—C9—C11—C12 | 75.3 (3) | N2'—C9'—C11'—C16' | 101.8 (3) |
C10—C9—C11—C16 | 73.0 (3) | C10'—C9'—C11'—C12' | 104.4 (3) |
N2—C9—C11—C16 | −106.7 (3) | N2'—C9'—C11'—C12' | −79.2 (3) |
C16—C11—C12—C13 | 2.0 (3) | C16'—C11'—C12'—C13' | −2.6 (3) |
C9—C11—C12—C13 | 179.9 (2) | C9'—C11'—C12'—C13' | 178.4 (2) |
C11—C12—C13—C14 | −0.3 (4) | C11'—C12'—C13'—C14' | 0.8 (4) |
C12—C13—C14—C15 | −1.7 (4) | C12'—C13'—C14'—C15' | 1.6 (4) |
C13—C14—C15—C16 | 1.9 (4) | C13'—C14'—C15'—C16' | −2.2 (4) |
C14—C15—C16—C11 | −0.3 (4) | C14'—C15'—C16'—C11' | 0.3 (4) |
C12—C11—C16—C15 | −1.7 (3) | C12'—C11'—C16'—C15' | 2.1 (3) |
C9—C11—C16—C15 | −179.7 (2) | C9'—C11'—C16'—C15' | −179.0 (2) |
C9—C10—C17—C22 | 3.5 (4) | C9'—C10'—C17'—C22' | −4.0 (4) |
N3—C10—C17—C22 | −175.0 (2) | N3'—C10'—C17'—C22' | 175.0 (2) |
C9—C10—C17—C18 | −178.0 (2) | C9'—C10'—C17'—C18' | 177.1 (2) |
N3—C10—C17—C18 | 3.4 (3) | N3'—C10'—C17'—C18' | −3.9 (3) |
C22—C17—C18—C19 | 0.3 (3) | C22'—C17'—C18'—C19' | −0.4 (3) |
C10—C17—C18—C19 | −178.3 (2) | C10'—C17'—C18'—C19' | 178.5 (2) |
C17—C18—C19—C20 | −0.7 (4) | C17'—C18'—C19'—C20' | 0.8 (4) |
C18—C19—C20—C21 | 0.5 (4) | C18'—C19'—C20'—C21' | −0.6 (4) |
C19—C20—C21—C22 | 0.0 (4) | C19'—C20'—C21'—C22' | 0.0 (4) |
C20—C21—C22—C17 | −0.4 (4) | C20'—C21'—C22'—C17' | 0.4 (4) |
C18—C17—C22—C21 | 0.3 (3) | C18'—C17'—C22'—C21' | −0.2 (3) |
C10—C17—C22—C21 | 178.7 (2) | C10'—C17'—C22'—C21' | −179.1 (2) |