Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807008628/dn2125sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807008628/dn21253sup2.hkl |
CCDC reference: 642967
Data collection: CrysAlis CCD (Oxford Diffraction, 2004); cell refinement: CrysAlis RED (Oxford Diffraction, 2004); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 pour Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
C39H32ClN7O4 | F(000) = 1456 |
Mr = 698.17 | Dx = 1.327 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 6144 reflections |
a = 17.3927 (9) Å | θ = 3.2–25.0° |
b = 9.2018 (5) Å | µ = 0.16 mm−1 |
c = 22.846 (1) Å | T = 295 K |
β = 107.102 (5)° | Parallelepiped, orange |
V = 3494.7 (3) Å3 | 0.55 × 0.48 × 0.17 mm |
Z = 4 |
Oxford Xcalibur CCD diffractometer | 5135 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.057 |
Graphite monochromator | θmax = 25.0°, θmin = 3.2° |
ω scans | h = 0→20 |
59211 measured reflections | k = 0→10 |
6144 independent reflections | l = −27→25 |
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)] = 0.075 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.190 | H-atom parameters constrained |
S = 1.12 | w = 1/[σ2(Fo2) + (0.073P)2 + 3.0925P] where P = (Fo2 + 2Fc2)/3 |
6144 reflections | (Δ/σ)max < 0.001 |
462 parameters | Δρmax = 0.32 e Å−3 |
0 restraints | Δρmin = −0.40 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. Some disorder appears at the ethyl group as shown by the high values of equivalent ADPs for atoms C32 and C33. Despite the lower isotropic displacement parameters for the atoms, attemps to take into account such a disorder by splitting (PART instruction of SHELXL) the involved atoms (C32, C33, O3, O4 and even O1, O2 and Cl) did not improve the overall refinement. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.12141 (7) | 0.0944 (2) | 0.71263 (6) | 0.1356 (7) | |
O1 | 0.3092 (4) | 0.3697 (4) | 0.82507 (14) | 0.167 (2) | |
O2 | 0.32880 (16) | 0.6029 (3) | 0.83280 (10) | 0.0727 (7) | |
O3 | 0.5235 (3) | 0.9240 (4) | 1.24730 (14) | 0.1225 (14) | |
O4 | 0.4763 (3) | 1.0892 (4) | 1.18056 (15) | 0.1249 (14) | |
N1 | 0.17697 (14) | 0.2407 (3) | 1.05111 (11) | 0.0472 (6) | |
N2 | 0.10541 (14) | 0.2030 (3) | 1.00552 (12) | 0.0534 (6) | |
N3 | 0.19951 (13) | 0.2556 (3) | 0.95796 (10) | 0.0426 (5) | |
N4 | 0.37299 (14) | 0.5394 (3) | 1.01583 (10) | 0.0452 (6) | |
N5 | 0.35403 (14) | 0.5876 (3) | 0.95535 (10) | 0.0451 (6) | |
N6 | 0.35053 (15) | 0.3455 (3) | 0.95440 (11) | 0.0490 (6) | |
N7 | 0.4870 (2) | 0.9620 (4) | 1.19538 (15) | 0.0820 (10) | |
C1 | 0.12048 (17) | 0.2068 (3) | 0.95408 (14) | 0.0491 (7) | |
C2 | 0.22629 (16) | 0.3296 (3) | 1.01820 (12) | 0.0402 (6) | |
C3 | 0.31528 (15) | 0.3124 (3) | 1.05140 (12) | 0.0417 (6) | |
H3A | 0.3268 | 0.2094 | 1.0573 | 0.050* | |
H3B | 0.3257 | 0.3558 | 1.0917 | 0.050* | |
C4 | 0.37507 (16) | 0.3785 (3) | 1.02054 (13) | 0.0422 (6) | |
C5 | 0.34018 (16) | 0.4724 (3) | 0.92237 (13) | 0.0447 (7) | |
C6 | 0.32379 (17) | 0.2032 (3) | 0.93408 (13) | 0.0454 (7) | |
C7 | 0.25002 (17) | 0.1561 (3) | 0.93826 (13) | 0.0427 (6) | |
C8 | 0.22593 (19) | 0.0152 (3) | 0.91954 (14) | 0.0523 (7) | |
H8 | 0.1769 | −0.0194 | 0.9223 | 0.063* | |
C9 | 0.2743 (2) | −0.0732 (3) | 0.89690 (15) | 0.0608 (9) | |
H9 | 0.2572 | −0.1666 | 0.8839 | 0.073* | |
C10 | 0.3471 (2) | −0.0256 (4) | 0.89331 (16) | 0.0661 (9) | |
H10 | 0.3793 | −0.0861 | 0.8778 | 0.079* | |
C11 | 0.3726 (2) | 0.1123 (4) | 0.91273 (16) | 0.0612 (9) | |
H11 | 0.4228 | 0.1443 | 0.9115 | 0.073* | |
C12 | 0.16449 (19) | 0.2969 (4) | 1.10572 (14) | 0.0541 (8) | |
C13 | 0.0967 (2) | 0.3747 (5) | 1.10533 (17) | 0.0715 (10) | |
H13 | 0.0555 | 0.3861 | 1.0689 | 0.086* | |
C14 | 0.0895 (3) | 0.4357 (6) | 1.1585 (2) | 0.0983 (15) | |
H14 | 0.0431 | 0.4865 | 1.1579 | 0.118* | |
C15 | 0.1501 (3) | 0.4223 (7) | 1.2123 (2) | 0.1053 (17) | |
H15 | 0.1460 | 0.4676 | 1.2476 | 0.126* | |
C16 | 0.2170 (3) | 0.3415 (6) | 1.21371 (17) | 0.0931 (15) | |
H16 | 0.2574 | 0.3296 | 1.2505 | 0.112* | |
C17 | 0.2248 (2) | 0.2771 (4) | 1.16056 (16) | 0.0710 (10) | |
H17 | 0.2699 | 0.2216 | 1.1618 | 0.085* | |
C18 | 0.06117 (17) | 0.1747 (4) | 0.89508 (15) | 0.0567 (8) | |
C19 | 0.0720 (2) | 0.2306 (4) | 0.84194 (16) | 0.0648 (9) | |
H19 | 0.1179 | 0.2847 | 0.8439 | 0.078* | |
C20 | 0.0150 (2) | 0.2068 (5) | 0.78549 (17) | 0.0754 (11) | |
H20 | 0.0220 | 0.2460 | 0.7499 | 0.091* | |
C21 | −0.0514 (2) | 0.1247 (5) | 0.78342 (19) | 0.0842 (13) | |
C22 | −0.0624 (2) | 0.0644 (6) | 0.8352 (2) | 0.0930 (15) | |
H22 | −0.1072 | 0.0068 | 0.8326 | 0.112* | |
C23 | −0.0063 (2) | 0.0898 (5) | 0.89173 (19) | 0.0762 (11) | |
H23 | −0.0137 | 0.0503 | 0.9271 | 0.091* | |
C24 | 0.19779 (15) | 0.4875 (3) | 1.01197 (12) | 0.0399 (6) | |
C25 | 0.15091 (17) | 0.5444 (3) | 0.95697 (13) | 0.0487 (7) | |
H25 | 0.1395 | 0.4877 | 0.9218 | 0.058* | |
C26 | 0.12069 (19) | 0.6846 (4) | 0.95347 (16) | 0.0596 (8) | |
H26 | 0.0893 | 0.7207 | 0.9161 | 0.072* | |
C27 | 0.1367 (2) | 0.7703 (4) | 1.00460 (17) | 0.0657 (9) | |
H27 | 0.1150 | 0.8632 | 1.0023 | 0.079* | |
C28 | 0.1851 (2) | 0.7179 (4) | 1.05926 (16) | 0.0595 (8) | |
H28 | 0.1976 | 0.7768 | 1.0939 | 0.071* | |
C29 | 0.21539 (19) | 0.5782 (3) | 1.06324 (13) | 0.0504 (7) | |
H29 | 0.2480 | 0.5440 | 1.1006 | 0.060* | |
C30 | 0.45928 (18) | 0.3166 (4) | 1.05014 (16) | 0.0598 (8) | |
H30A | 0.4699 | 0.3147 | 1.0938 | 0.090* | |
H30B | 0.4985 | 0.3767 | 1.0398 | 0.090* | |
H30C | 0.4622 | 0.2197 | 1.0354 | 0.090* | |
C31 | 0.39977 (16) | 0.6408 (3) | 1.06123 (12) | 0.0428 (6) | |
C32 | 0.4338 (2) | 0.6023 (3) | 1.12269 (13) | 0.0552 (8) | |
H32 | 0.4374 | 0.5049 | 1.1341 | 0.066* | |
C33 | 0.4621 (2) | 0.7082 (4) | 1.16622 (14) | 0.0620 (9) | |
H33 | 0.4860 | 0.6826 | 1.2069 | 0.074* | |
C34 | 0.4550 (2) | 0.8516 (3) | 1.14937 (14) | 0.0548 (8) | |
C35 | 0.4191 (2) | 0.8919 (3) | 1.08998 (15) | 0.0565 (8) | |
H35 | 0.4134 | 0.9898 | 1.0795 | 0.068* | |
C36 | 0.39173 (18) | 0.7880 (3) | 1.04606 (14) | 0.0514 (7) | |
H36 | 0.3675 | 0.8156 | 1.0057 | 0.062* | |
C37 | 0.3242 (2) | 0.4751 (4) | 0.85504 (15) | 0.0645 (9) | |
C38 | 0.3181 (3) | 0.6116 (6) | 0.76703 (17) | 0.0971 (15) | |
H38A | 0.3650 | 0.5717 | 0.7580 | 0.116* | |
H38B | 0.2716 | 0.5546 | 0.7451 | 0.116* | |
C39 | 0.3069 (4) | 0.7597 (6) | 0.7471 (2) | 0.125 (2) | |
H39A | 0.2978 | 0.7639 | 0.7036 | 0.187* | |
H39B | 0.3542 | 0.8148 | 0.7672 | 0.187* | |
H39C | 0.2614 | 0.7997 | 0.7571 | 0.187* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0736 (7) | 0.2261 (19) | 0.0862 (8) | −0.0016 (9) | −0.0087 (6) | −0.0690 (10) |
O1 | 0.332 (7) | 0.080 (2) | 0.0524 (18) | −0.021 (3) | −0.003 (3) | −0.0129 (17) |
O2 | 0.0951 (19) | 0.0816 (18) | 0.0400 (12) | −0.0116 (14) | 0.0179 (12) | 0.0042 (12) |
O3 | 0.197 (4) | 0.094 (2) | 0.0536 (17) | −0.024 (2) | 0.001 (2) | −0.0189 (16) |
O4 | 0.225 (4) | 0.0615 (19) | 0.080 (2) | −0.020 (2) | 0.031 (2) | −0.0189 (16) |
N1 | 0.0384 (12) | 0.0543 (15) | 0.0484 (14) | −0.0083 (11) | 0.0119 (10) | 0.0047 (11) |
N2 | 0.0418 (13) | 0.0605 (16) | 0.0560 (16) | −0.0106 (12) | 0.0115 (11) | −0.0037 (13) |
N3 | 0.0363 (12) | 0.0466 (13) | 0.0432 (13) | −0.0033 (10) | 0.0091 (10) | −0.0058 (10) |
N4 | 0.0505 (13) | 0.0441 (13) | 0.0391 (12) | −0.0125 (11) | 0.0101 (10) | 0.0014 (10) |
N5 | 0.0447 (13) | 0.0498 (14) | 0.0365 (12) | −0.0075 (11) | 0.0053 (10) | 0.0034 (11) |
N6 | 0.0541 (14) | 0.0489 (15) | 0.0462 (14) | −0.0091 (12) | 0.0181 (11) | −0.0026 (11) |
N7 | 0.125 (3) | 0.065 (2) | 0.059 (2) | −0.016 (2) | 0.032 (2) | −0.0181 (17) |
C1 | 0.0385 (15) | 0.0565 (18) | 0.0536 (18) | −0.0056 (13) | 0.0155 (13) | −0.0040 (14) |
C2 | 0.0400 (14) | 0.0452 (16) | 0.0345 (13) | −0.0042 (12) | 0.0096 (11) | 0.0008 (12) |
C3 | 0.0386 (14) | 0.0401 (15) | 0.0446 (15) | −0.0010 (12) | 0.0092 (12) | 0.0041 (12) |
C4 | 0.0411 (14) | 0.0411 (15) | 0.0435 (15) | −0.0045 (12) | 0.0110 (12) | 0.0022 (12) |
C5 | 0.0354 (14) | 0.0531 (18) | 0.0434 (15) | −0.0052 (13) | 0.0081 (12) | 0.0005 (14) |
C6 | 0.0448 (15) | 0.0419 (16) | 0.0504 (16) | −0.0033 (13) | 0.0156 (13) | −0.0044 (13) |
C7 | 0.0450 (15) | 0.0383 (15) | 0.0447 (15) | −0.0006 (12) | 0.0130 (12) | −0.0013 (12) |
C8 | 0.0526 (17) | 0.0449 (17) | 0.0568 (18) | −0.0060 (14) | 0.0121 (14) | −0.0009 (14) |
C9 | 0.075 (2) | 0.0395 (17) | 0.061 (2) | 0.0052 (16) | 0.0098 (17) | −0.0055 (15) |
C10 | 0.068 (2) | 0.062 (2) | 0.068 (2) | 0.0147 (18) | 0.0188 (18) | −0.0137 (18) |
C11 | 0.0485 (17) | 0.073 (2) | 0.065 (2) | 0.0007 (16) | 0.0225 (16) | −0.0120 (18) |
C12 | 0.0554 (18) | 0.065 (2) | 0.0452 (17) | −0.0130 (16) | 0.0199 (14) | 0.0073 (15) |
C13 | 0.056 (2) | 0.108 (3) | 0.056 (2) | −0.011 (2) | 0.0253 (16) | −0.005 (2) |
C14 | 0.079 (3) | 0.149 (5) | 0.080 (3) | −0.017 (3) | 0.045 (2) | −0.024 (3) |
C15 | 0.109 (4) | 0.150 (5) | 0.072 (3) | −0.040 (4) | 0.050 (3) | −0.021 (3) |
C16 | 0.110 (4) | 0.123 (4) | 0.041 (2) | −0.038 (3) | 0.013 (2) | 0.011 (2) |
C17 | 0.072 (2) | 0.083 (3) | 0.054 (2) | −0.012 (2) | 0.0136 (17) | 0.0213 (19) |
C18 | 0.0381 (15) | 0.071 (2) | 0.0590 (19) | −0.0039 (15) | 0.0109 (14) | −0.0177 (17) |
C19 | 0.0488 (18) | 0.083 (3) | 0.060 (2) | −0.0025 (17) | 0.0112 (15) | −0.0132 (18) |
C20 | 0.060 (2) | 0.106 (3) | 0.057 (2) | 0.008 (2) | 0.0112 (17) | −0.023 (2) |
C21 | 0.049 (2) | 0.124 (4) | 0.071 (3) | 0.004 (2) | 0.0049 (18) | −0.042 (3) |
C22 | 0.046 (2) | 0.133 (4) | 0.094 (3) | −0.020 (2) | 0.011 (2) | −0.041 (3) |
C23 | 0.0455 (19) | 0.105 (3) | 0.078 (2) | −0.0151 (19) | 0.0183 (17) | −0.021 (2) |
C24 | 0.0367 (14) | 0.0437 (15) | 0.0406 (14) | 0.0009 (12) | 0.0134 (11) | 0.0034 (12) |
C25 | 0.0459 (16) | 0.0536 (18) | 0.0443 (16) | 0.0014 (14) | 0.0096 (13) | 0.0062 (14) |
C26 | 0.0539 (18) | 0.059 (2) | 0.062 (2) | 0.0110 (16) | 0.0099 (15) | 0.0149 (17) |
C27 | 0.072 (2) | 0.053 (2) | 0.079 (2) | 0.0185 (17) | 0.0333 (19) | 0.0143 (18) |
C28 | 0.074 (2) | 0.0505 (19) | 0.061 (2) | 0.0052 (16) | 0.0312 (17) | −0.0054 (16) |
C29 | 0.0544 (17) | 0.0555 (18) | 0.0418 (16) | 0.0028 (14) | 0.0148 (13) | 0.0042 (14) |
C30 | 0.0406 (16) | 0.067 (2) | 0.070 (2) | 0.0019 (15) | 0.0130 (15) | 0.0048 (17) |
C31 | 0.0418 (14) | 0.0443 (16) | 0.0406 (15) | −0.0054 (12) | 0.0096 (12) | −0.0004 (12) |
C32 | 0.078 (2) | 0.0437 (17) | 0.0406 (16) | −0.0074 (15) | 0.0116 (15) | 0.0055 (13) |
C33 | 0.081 (2) | 0.064 (2) | 0.0389 (16) | −0.0112 (18) | 0.0138 (15) | 0.0000 (15) |
C34 | 0.068 (2) | 0.0514 (19) | 0.0470 (17) | −0.0076 (15) | 0.0200 (15) | −0.0086 (14) |
C35 | 0.073 (2) | 0.0426 (17) | 0.0559 (19) | −0.0011 (15) | 0.0214 (16) | −0.0014 (14) |
C36 | 0.0571 (18) | 0.0475 (18) | 0.0437 (16) | 0.0003 (14) | 0.0056 (14) | 0.0022 (14) |
C37 | 0.079 (2) | 0.059 (2) | 0.0447 (17) | −0.0061 (18) | 0.0017 (16) | −0.0071 (17) |
C38 | 0.123 (4) | 0.124 (4) | 0.044 (2) | 0.006 (3) | 0.023 (2) | 0.009 (2) |
C39 | 0.190 (6) | 0.120 (4) | 0.066 (3) | −0.027 (4) | 0.041 (3) | 0.024 (3) |
Cl1—C21 | 1.737 (4) | C11—C10 | 1.373 (5) |
O2—C37 | 1.292 (4) | C11—H11 | 0.9300 |
O2—C38 | 1.461 (4) | C35—C34 | 1.367 (4) |
O4—N7 | 1.218 (4) | C35—H35 | 0.9300 |
O3—N7 | 1.220 (4) | C8—C9 | 1.376 (5) |
O1—C37 | 1.172 (4) | C8—C7 | 1.390 (4) |
N4—C31 | 1.371 (4) | C8—H8 | 0.9300 |
N4—N5 | 1.395 (3) | C34—C33 | 1.370 (5) |
N4—C4 | 1.484 (4) | C33—H33 | 0.9300 |
N5—C5 | 1.282 (4) | C9—C10 | 1.365 (5) |
N1—N2 | 1.411 (3) | C9—H9 | 0.9300 |
N1—C12 | 1.425 (4) | C18—C19 | 1.382 (5) |
N1—C2 | 1.533 (3) | C18—C23 | 1.392 (5) |
N2—C1 | 1.278 (4) | C19—C20 | 1.393 (5) |
N7—C34 | 1.451 (4) | C19—H19 | 0.9300 |
C4—N6 | 1.476 (4) | C10—H10 | 0.9300 |
C4—C30 | 1.531 (4) | C28—C27 | 1.372 (5) |
C4—C3 | 1.542 (4) | C28—H28 | 0.9300 |
C2—N3 | 1.483 (3) | C27—C26 | 1.368 (5) |
C2—C3 | 1.518 (4) | C27—H27 | 0.9300 |
C2—C24 | 1.528 (4) | C26—H26 | 0.9300 |
N3—C1 | 1.424 (4) | C30—H30A | 0.9600 |
N3—C7 | 1.430 (4) | C30—H30B | 0.9600 |
N6—C5 | 1.362 (4) | C30—H30C | 0.9600 |
N6—C6 | 1.421 (4) | C13—C14 | 1.376 (5) |
C25—C24 | 1.384 (4) | C13—H13 | 0.9300 |
C25—C26 | 1.386 (4) | C23—C22 | 1.390 (5) |
C25—H25 | 0.9300 | C23—H23 | 0.9300 |
C24—C29 | 1.397 (4) | C21—C20 | 1.370 (6) |
C3—H3A | 0.9700 | C21—C22 | 1.371 (6) |
C3—H3B | 0.9700 | C20—H20 | 0.9300 |
C5—C37 | 1.481 (4) | C17—C16 | 1.393 (6) |
C31—C36 | 1.395 (4) | C17—H17 | 0.9300 |
C31—C32 | 1.400 (4) | C16—C15 | 1.372 (7) |
C12—C13 | 1.378 (5) | C16—H16 | 0.9300 |
C12—C17 | 1.389 (5) | C38—C39 | 1.432 (7) |
C29—C28 | 1.383 (4) | C38—H38A | 0.9700 |
C29—H29 | 0.9300 | C38—H38B | 0.9700 |
C6—C11 | 1.379 (4) | C22—H22 | 0.9300 |
C6—C7 | 1.384 (4) | C14—C15 | 1.369 (7) |
C32—C33 | 1.376 (4) | C14—H14 | 0.9300 |
C32—H32 | 0.9300 | C15—H15 | 0.9300 |
C36—C35 | 1.367 (4) | C39—H39A | 0.9600 |
C36—H36 | 0.9300 | C39—H39B | 0.9600 |
C1—C18 | 1.467 (4) | C39—H39C | 0.9600 |
C37—O2—C38 | 116.7 (3) | C33—C34—N7 | 119.2 (3) |
C31—N4—N5 | 117.5 (2) | C34—C33—C32 | 119.7 (3) |
C31—N4—C4 | 128.9 (2) | C34—C33—H33 | 120.1 |
N5—N4—C4 | 112.5 (2) | C32—C33—H33 | 120.1 |
C5—N5—N4 | 105.5 (2) | C6—C7—C8 | 118.2 (3) |
N2—N1—C12 | 114.0 (2) | C6—C7—N3 | 119.2 (2) |
N2—N1—C2 | 105.6 (2) | C8—C7—N3 | 122.4 (3) |
C12—N1—C2 | 119.2 (2) | C10—C9—C8 | 120.9 (3) |
C1—N2—N1 | 107.3 (2) | C10—C9—H9 | 119.5 |
O4—N7—O3 | 122.6 (3) | C8—C9—H9 | 119.5 |
O4—N7—C34 | 118.5 (3) | C19—C18—C23 | 119.4 (3) |
O3—N7—C34 | 118.9 (3) | C19—C18—C1 | 119.5 (3) |
N6—C4—N4 | 97.9 (2) | C23—C18—C1 | 121.1 (3) |
N6—C4—C30 | 109.1 (2) | C18—C19—C20 | 120.7 (3) |
N4—C4—C30 | 113.7 (2) | C18—C19—H19 | 119.6 |
N6—C4—C3 | 110.9 (2) | C20—C19—H19 | 119.6 |
N4—C4—C3 | 114.9 (2) | C9—C10—C11 | 119.6 (3) |
C30—C4—C3 | 109.7 (2) | C9—C10—H10 | 120.2 |
N3—C2—C3 | 114.3 (2) | C11—C10—H10 | 120.2 |
N3—C2—C24 | 110.2 (2) | C27—C28—C29 | 120.4 (3) |
C3—C2—C24 | 113.6 (2) | C27—C28—H28 | 119.8 |
N3—C2—N1 | 98.2 (2) | C29—C28—H28 | 119.8 |
C3—C2—N1 | 109.6 (2) | C26—C27—C28 | 119.4 (3) |
C24—C2—N1 | 109.9 (2) | C26—C27—H27 | 120.3 |
C1—N3—C7 | 116.7 (2) | C28—C27—H27 | 120.3 |
C1—N3—C2 | 103.7 (2) | C27—C26—C25 | 120.5 (3) |
C7—N3—C2 | 122.1 (2) | C27—C26—H26 | 119.7 |
C5—N6—C6 | 129.5 (2) | C25—C26—H26 | 119.7 |
C5—N6—C4 | 109.1 (2) | O1—C37—O2 | 123.5 (3) |
C6—N6—C4 | 119.5 (2) | O1—C37—C5 | 122.3 (4) |
C24—C25—C26 | 121.1 (3) | O2—C37—C5 | 114.2 (3) |
C24—C25—H25 | 119.4 | C4—C30—H30A | 109.5 |
C26—C25—H25 | 119.4 | C4—C30—H30B | 109.5 |
C25—C24—C29 | 117.4 (3) | H30A—C30—H30B | 109.5 |
C25—C24—C2 | 122.2 (3) | C4—C30—H30C | 109.5 |
C29—C24—C2 | 120.3 (2) | H30A—C30—H30C | 109.5 |
C2—C3—C4 | 117.1 (2) | H30B—C30—H30C | 109.5 |
C2—C3—H3A | 108.0 | C14—C13—C12 | 120.3 (4) |
C4—C3—H3A | 108.0 | C14—C13—H13 | 119.8 |
C2—C3—H3B | 108.0 | C12—C13—H13 | 119.8 |
C4—C3—H3B | 108.0 | C22—C23—C18 | 119.7 (4) |
H3A—C3—H3B | 107.3 | C22—C23—H23 | 120.1 |
N5—C5—N6 | 114.9 (2) | C18—C23—H23 | 120.1 |
N5—C5—C37 | 122.8 (3) | C20—C21—C22 | 121.6 (4) |
N6—C5—C37 | 121.8 (3) | C20—C21—Cl1 | 118.3 (4) |
N4—C31—C36 | 119.1 (3) | C22—C21—Cl1 | 120.1 (3) |
N4—C31—C32 | 122.4 (3) | C21—C20—C19 | 118.8 (4) |
C36—C31—C32 | 118.5 (3) | C21—C20—H20 | 120.6 |
C13—C12—C17 | 119.5 (3) | C19—C20—H20 | 120.6 |
C13—C12—N1 | 122.2 (3) | C12—C17—C16 | 119.3 (4) |
C17—C12—N1 | 118.2 (3) | C12—C17—H17 | 120.4 |
C28—C29—C24 | 121.0 (3) | C16—C17—H17 | 120.4 |
C28—C29—H29 | 119.5 | C15—C16—C17 | 120.6 (4) |
C24—C29—H29 | 119.5 | C15—C16—H16 | 119.7 |
C11—C6—C7 | 120.9 (3) | C17—C16—H16 | 119.7 |
C11—C6—N6 | 119.9 (3) | C39—C38—O2 | 110.1 (4) |
C7—C6—N6 | 119.2 (3) | C39—C38—H38A | 109.6 |
C33—C32—C31 | 120.1 (3) | O2—C38—H38A | 109.6 |
C33—C32—H32 | 119.9 | C39—C38—H38B | 109.6 |
C31—C32—H32 | 119.9 | O2—C38—H38B | 109.6 |
C35—C36—C31 | 120.6 (3) | H38A—C38—H38B | 108.2 |
C35—C36—H36 | 119.7 | C21—C22—C23 | 119.7 (4) |
C31—C36—H36 | 119.7 | C21—C22—H22 | 120.2 |
N2—C1—N3 | 114.0 (3) | C23—C22—H22 | 120.2 |
N2—C1—C18 | 124.1 (3) | C15—C14—C13 | 120.7 (5) |
N3—C1—C18 | 121.7 (3) | C15—C14—H14 | 119.7 |
C10—C11—C6 | 120.1 (3) | C13—C14—H14 | 119.7 |
C10—C11—H11 | 119.9 | C14—C15—C16 | 119.6 (4) |
C6—C11—H11 | 119.9 | C14—C15—H15 | 120.2 |
C36—C35—C34 | 119.8 (3) | C16—C15—H15 | 120.2 |
C36—C35—H35 | 120.1 | C38—C39—H39A | 109.5 |
C34—C35—H35 | 120.1 | C38—C39—H39B | 109.5 |
C9—C8—C7 | 120.3 (3) | H39A—C39—H39B | 109.5 |
C9—C8—H8 | 119.9 | C38—C39—H39C | 109.5 |
C7—C8—H8 | 119.9 | H39A—C39—H39C | 109.5 |
C35—C34—C33 | 121.2 (3) | H39B—C39—H39C | 109.5 |
C35—C34—N7 | 119.7 (3) | ||
C31—N4—N5—C5 | 172.5 (2) | C32—C31—C36—C35 | 2.3 (5) |
C4—N4—N5—C5 | 3.3 (3) | N1—N2—C1—N3 | −4.0 (4) |
C12—N1—N2—C1 | 156.5 (3) | N1—N2—C1—C18 | −179.7 (3) |
C2—N1—N2—C1 | 23.8 (3) | C7—N3—C1—N2 | 119.4 (3) |
C31—N4—C4—N6 | −170.5 (3) | C2—N3—C1—N2 | −17.9 (3) |
N5—N4—C4—N6 | −2.8 (3) | C7—N3—C1—C18 | −64.8 (4) |
C31—N4—C4—C30 | −55.6 (4) | C2—N3—C1—C18 | 157.9 (3) |
N5—N4—C4—C30 | 112.1 (3) | C7—C6—C11—C10 | 2.2 (5) |
C31—N4—C4—C3 | 72.0 (4) | N6—C6—C11—C10 | 179.7 (3) |
N5—N4—C4—C3 | −120.2 (2) | C31—C36—C35—C34 | 0.1 (5) |
N2—N1—C2—N3 | −32.5 (3) | C36—C35—C34—C33 | −1.8 (5) |
C12—N1—C2—N3 | −162.2 (2) | C36—C35—C34—N7 | 177.4 (3) |
N2—N1—C2—C3 | −152.0 (2) | O4—N7—C34—C35 | 4.9 (6) |
C12—N1—C2—C3 | 78.3 (3) | O3—N7—C34—C35 | −175.2 (4) |
N2—N1—C2—C24 | 82.5 (3) | O4—N7—C34—C33 | −176.0 (4) |
C12—N1—C2—C24 | −47.2 (3) | O3—N7—C34—C33 | 4.0 (6) |
C3—C2—N3—C1 | 144.9 (2) | C35—C34—C33—C32 | 0.9 (5) |
C24—C2—N3—C1 | −85.7 (3) | N7—C34—C33—C32 | −178.3 (3) |
N1—C2—N3—C1 | 29.0 (3) | C31—C32—C33—C34 | 1.6 (5) |
C3—C2—N3—C7 | 10.5 (4) | C11—C6—C7—C8 | −0.9 (4) |
C24—C2—N3—C7 | 139.9 (2) | N6—C6—C7—C8 | −178.4 (3) |
N1—C2—N3—C7 | −105.3 (3) | C11—C6—C7—N3 | −177.1 (3) |
N4—C4—N6—C5 | 1.4 (3) | N6—C6—C7—N3 | 5.3 (4) |
C30—C4—N6—C5 | −117.2 (3) | C9—C8—C7—C6 | −0.7 (4) |
C3—C4—N6—C5 | 121.9 (2) | C9—C8—C7—N3 | 175.4 (3) |
N4—C4—N6—C6 | −164.1 (2) | C1—N3—C7—C6 | 172.4 (3) |
C30—C4—N6—C6 | 77.3 (3) | C2—N3—C7—C6 | −58.7 (4) |
C3—C4—N6—C6 | −43.6 (3) | C1—N3—C7—C8 | −3.7 (4) |
C26—C25—C24—C29 | −1.9 (4) | C2—N3—C7—C8 | 125.2 (3) |
C26—C25—C24—C2 | 175.0 (3) | C7—C8—C9—C10 | 1.1 (5) |
N3—C2—C24—C25 | 2.5 (3) | N2—C1—C18—C19 | 156.4 (3) |
C3—C2—C24—C25 | 132.2 (3) | N3—C1—C18—C19 | −19.0 (5) |
N1—C2—C24—C25 | −104.6 (3) | N2—C1—C18—C23 | −23.0 (5) |
N3—C2—C24—C29 | 179.3 (2) | N3—C1—C18—C23 | 161.6 (3) |
C3—C2—C24—C29 | −50.9 (3) | C23—C18—C19—C20 | 2.0 (5) |
N1—C2—C24—C29 | 72.2 (3) | C1—C18—C19—C20 | −177.4 (3) |
N3—C2—C3—C4 | 63.5 (3) | C8—C9—C10—C11 | 0.2 (5) |
C24—C2—C3—C4 | −64.1 (3) | C6—C11—C10—C9 | −1.8 (5) |
N1—C2—C3—C4 | 172.6 (2) | C24—C29—C28—C27 | 0.2 (5) |
N6—C4—C3—C2 | −44.0 (3) | C29—C28—C27—C26 | −2.1 (5) |
N4—C4—C3—C2 | 65.8 (3) | C28—C27—C26—C25 | 1.9 (5) |
C30—C4—C3—C2 | −164.6 (3) | C24—C25—C26—C27 | 0.1 (5) |
N4—N5—C5—N6 | −2.3 (3) | C38—O2—C37—O1 | −2.9 (7) |
N4—N5—C5—C37 | −174.8 (3) | C38—O2—C37—C5 | 176.7 (3) |
C6—N6—C5—N5 | 164.1 (3) | N5—C5—C37—O1 | −177.6 (5) |
C4—N6—C5—N5 | 0.5 (3) | N6—C5—C37—O1 | 10.3 (6) |
C6—N6—C5—C37 | −23.3 (5) | N5—C5—C37—O2 | 2.7 (5) |
C4—N6—C5—C37 | 173.1 (3) | N6—C5—C37—O2 | −169.4 (3) |
N5—N4—C31—C36 | 12.7 (4) | C17—C12—C13—C14 | 1.7 (6) |
C4—N4—C31—C36 | 179.9 (3) | N1—C12—C13—C14 | −175.4 (4) |
N5—N4—C31—C32 | −168.4 (3) | C19—C18—C23—C22 | −1.0 (6) |
C4—N4—C31—C32 | −1.2 (5) | C1—C18—C23—C22 | 178.4 (4) |
N2—N1—C12—C13 | −31.1 (4) | C22—C21—C20—C19 | −0.8 (6) |
C2—N1—C12—C13 | 94.8 (4) | Cl1—C21—C20—C19 | −179.3 (3) |
N2—N1—C12—C17 | 151.8 (3) | C18—C19—C20—C21 | −1.1 (6) |
C2—N1—C12—C17 | −82.4 (4) | C13—C12—C17—C16 | −2.6 (5) |
C25—C24—C29—C28 | 1.8 (4) | N1—C12—C17—C16 | 174.6 (3) |
C2—C24—C29—C28 | −175.2 (3) | C12—C17—C16—C15 | 0.7 (6) |
C5—N6—C6—C11 | 91.0 (4) | C37—O2—C38—C39 | 167.3 (4) |
C4—N6—C6—C11 | −106.8 (3) | C20—C21—C22—C23 | 1.8 (7) |
C5—N6—C6—C7 | −91.5 (4) | Cl1—C21—C22—C23 | −179.7 (3) |
C4—N6—C6—C7 | 70.7 (4) | C18—C23—C22—C21 | −0.9 (7) |
N4—C31—C32—C33 | 177.9 (3) | C12—C13—C14—C15 | 1.1 (7) |
C36—C31—C32—C33 | −3.2 (5) | C13—C14—C15—C16 | −3.0 (8) |
N4—C31—C36—C35 | −178.8 (3) | C17—C16—C15—C14 | 2.1 (7) |