Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807009075/bi2163sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807009075/bi2163Isup2.hkl |
CCDC reference: 642915
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C20H17N5 | F(000) = 1376 |
Mr = 327.39 | Dx = 1.279 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1958 reflections |
a = 17.148 (6) Å | θ = 2.2–22.9° |
b = 18.399 (6) Å | µ = 0.08 mm−1 |
c = 10.847 (4) Å | T = 298 K |
β = 96.606 (5)° | Block, yellow |
V = 3399 (2) Å3 | 0.30 × 0.20 × 0.20 mm |
Z = 8 |
Siemens SMART CCD area-detector diffractometer | 5977 independent reflections |
Radiation source: fine-focus sealed tube | 3272 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.037 |
ω scans | θmax = 25.0°, θmin = 1.2° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −20→19 |
Tmin = 0.977, Tmax = 0.984 | k = −20→21 |
13510 measured reflections | l = −12→8 |
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)] = 0.050 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.143 | H-atom parameters constrained |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0537P)2 + 0.0985P] where P = (Fo2 + 2Fc2)/3 |
5977 reflections | (Δ/σ)max < 0.001 |
455 parameters | Δρmax = 0.15 e Å−3 |
0 restraints | Δρmin = −0.13 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 | ||
N1 | 0.37859 (12) | 0.50530 (11) | 0.33298 (19) | 0.0627 (6) | |
N2 | 0.39479 (12) | 0.39715 (11) | 0.21793 (19) | 0.0622 (5) | |
N3 | 0.25937 (11) | 0.41247 (10) | 0.26035 (17) | 0.0551 (5) | |
H3 | 0.2632 | 0.4529 | 0.3003 | 0.066* | |
N4 | 0.11944 (12) | 0.39085 (11) | 0.25376 (19) | 0.0629 (6) | |
N5 | 0.15077 (12) | 0.47215 (11) | 0.4213 (2) | 0.0652 (6) | |
N6 | 0.36719 (11) | 0.68562 (11) | 0.13647 (18) | 0.0608 (5) | |
N7 | 0.37685 (11) | 0.57661 (11) | 0.01994 (18) | 0.0617 (5) | |
N8 | 0.24384 (10) | 0.59721 (9) | 0.06887 (17) | 0.0532 (5) | |
H8 | 0.2507 | 0.6360 | 0.1131 | 0.064* | |
N9 | 0.10225 (11) | 0.58579 (9) | 0.05332 (18) | 0.0553 (5) | |
N10 | 0.14021 (12) | 0.66993 (11) | 0.2158 (2) | 0.0631 (6) | |
C1 | 0.35631 (18) | 0.61330 (15) | 0.4474 (3) | 0.1009 (11) | |
H1A | 0.3077 | 0.6174 | 0.3943 | 0.151* | |
H1B | 0.3793 | 0.6606 | 0.4609 | 0.151* | |
H1C | 0.3466 | 0.5927 | 0.5255 | 0.151* | |
C2 | 0.41107 (17) | 0.56563 (14) | 0.3876 (3) | 0.0695 (7) | |
C3 | 0.48912 (18) | 0.58199 (15) | 0.3872 (3) | 0.0787 (8) | |
H3A | 0.5103 | 0.6232 | 0.4279 | 0.094* | |
C4 | 0.53552 (17) | 0.53704 (17) | 0.3263 (3) | 0.0830 (9) | |
H4 | 0.5883 | 0.5479 | 0.3242 | 0.100* | |
C5 | 0.50354 (16) | 0.47602 (15) | 0.2685 (3) | 0.0741 (8) | |
H5 | 0.5340 | 0.4451 | 0.2260 | 0.089* | |
C6 | 0.42457 (15) | 0.46127 (14) | 0.2746 (2) | 0.0598 (6) | |
C8 | 0.32227 (15) | 0.37816 (12) | 0.2152 (2) | 0.0553 (6) | |
C9 | 0.29015 (15) | 0.31092 (12) | 0.1570 (2) | 0.0588 (6) | |
C10 | 0.32674 (17) | 0.25569 (14) | 0.0975 (2) | 0.0698 (7) | |
H10 | 0.3804 | 0.2569 | 0.0913 | 0.084* | |
C11 | 0.2807 (2) | 0.19917 (15) | 0.0481 (2) | 0.0818 (9) | |
H11 | 0.3037 | 0.1618 | 0.0073 | 0.098* | |
C12 | 0.2010 (2) | 0.19675 (14) | 0.0577 (3) | 0.0815 (9) | |
H12 | 0.1713 | 0.1580 | 0.0230 | 0.098* | |
C13 | 0.16461 (17) | 0.25162 (14) | 0.1186 (2) | 0.0708 (7) | |
H13 | 0.1112 | 0.2499 | 0.1261 | 0.085* | |
C14 | 0.21032 (15) | 0.30855 (12) | 0.1674 (2) | 0.0579 (6) | |
C15 | 0.18951 (15) | 0.37438 (12) | 0.2340 (2) | 0.0551 (6) | |
C16 | 0.10259 (15) | 0.45381 (13) | 0.3196 (3) | 0.0607 (7) | |
C17 | 0.03408 (16) | 0.49088 (14) | 0.2815 (3) | 0.0708 (8) | |
H17 | 0.0013 | 0.4757 | 0.2120 | 0.085* | |
C18 | 0.01540 (18) | 0.55031 (16) | 0.3475 (3) | 0.0833 (9) | |
H18 | −0.0294 | 0.5773 | 0.3217 | 0.100* | |
C19 | 0.06319 (19) | 0.56985 (15) | 0.4521 (3) | 0.0807 (9) | |
H19 | 0.0509 | 0.6099 | 0.4983 | 0.097* | |
C20 | 0.13008 (17) | 0.52942 (15) | 0.4884 (3) | 0.0702 (8) | |
C22 | 0.18238 (19) | 0.54475 (17) | 0.6070 (3) | 0.0987 (10) | |
H22A | 0.2269 | 0.5128 | 0.6130 | 0.148* | |
H22B | 0.1535 | 0.5369 | 0.6766 | 0.148* | |
H22C | 0.2000 | 0.5943 | 0.6070 | 0.148* | |
C23 | 0.35228 (18) | 0.79534 (14) | 0.2556 (3) | 0.0949 (10) | |
H23A | 0.3004 | 0.7967 | 0.2116 | 0.142* | |
H23B | 0.3746 | 0.8432 | 0.2581 | 0.142* | |
H23C | 0.3496 | 0.7784 | 0.3387 | 0.142* | |
C24 | 0.40270 (16) | 0.74472 (14) | 0.1903 (2) | 0.0692 (7) | |
C25 | 0.48183 (18) | 0.75779 (16) | 0.1870 (3) | 0.0819 (8) | |
H25 | 0.5057 | 0.7979 | 0.2276 | 0.098* | |
C26 | 0.52462 (17) | 0.71116 (19) | 0.1234 (3) | 0.0877 (9) | |
H26 | 0.5776 | 0.7201 | 0.1188 | 0.105* | |
C27 | 0.48942 (15) | 0.65107 (17) | 0.0664 (3) | 0.0778 (8) | |
H27 | 0.5178 | 0.6191 | 0.0223 | 0.093* | |
C28 | 0.41033 (14) | 0.63908 (14) | 0.0761 (2) | 0.0605 (6) | |
C30 | 0.30400 (14) | 0.56040 (12) | 0.0195 (2) | 0.0527 (6) | |
C31 | 0.26709 (13) | 0.49506 (12) | −0.0399 (2) | 0.0523 (6) | |
C32 | 0.30040 (16) | 0.43834 (13) | −0.0992 (2) | 0.0651 (7) | |
H32 | 0.3537 | 0.4374 | −0.1080 | 0.078* | |
C33 | 0.25047 (17) | 0.38307 (14) | −0.1449 (2) | 0.0715 (8) | |
H33 | 0.2708 | 0.3439 | −0.1851 | 0.086* | |
C34 | 0.17113 (17) | 0.38462 (13) | −0.1324 (2) | 0.0695 (7) | |
H34 | 0.1393 | 0.3465 | −0.1639 | 0.083* | |
C35 | 0.13833 (15) | 0.44170 (12) | −0.0739 (2) | 0.0605 (7) | |
H35 | 0.0850 | 0.4428 | −0.0655 | 0.073* | |
C36 | 0.18777 (14) | 0.49700 (11) | −0.0285 (2) | 0.0495 (6) | |
C37 | 0.17135 (14) | 0.56399 (11) | 0.0384 (2) | 0.0497 (6) | |
C38 | 0.08932 (14) | 0.64982 (13) | 0.1186 (2) | 0.0551 (6) | |
C39 | 0.02035 (14) | 0.68735 (13) | 0.0828 (2) | 0.0634 (7) | |
H39 | −0.0145 | 0.6712 | 0.0165 | 0.076* | |
C40 | 0.00440 (17) | 0.74885 (15) | 0.1471 (3) | 0.0754 (8) | |
H40 | −0.0404 | 0.7761 | 0.1227 | 0.090* | |
C41 | 0.05539 (17) | 0.76955 (14) | 0.2476 (3) | 0.0738 (8) | |
H41 | 0.0452 | 0.8108 | 0.2927 | 0.089* | |
C42 | 0.12220 (15) | 0.72863 (14) | 0.2815 (3) | 0.0683 (7) | |
C44 | 0.17606 (18) | 0.74563 (17) | 0.3960 (3) | 0.1018 (11) | |
H44A | 0.2206 | 0.7137 | 0.4013 | 0.153* | |
H44B | 0.1487 | 0.7391 | 0.4676 | 0.153* | |
H44C | 0.1935 | 0.7951 | 0.3927 | 0.153* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0661 (14) | 0.0571 (12) | 0.0659 (14) | 0.0025 (11) | 0.0117 (11) | −0.0009 (11) |
N2 | 0.0592 (14) | 0.0609 (13) | 0.0668 (14) | 0.0058 (11) | 0.0077 (11) | −0.0013 (11) |
N3 | 0.0587 (13) | 0.0495 (11) | 0.0578 (13) | 0.0019 (10) | 0.0092 (10) | −0.0012 (10) |
N4 | 0.0607 (14) | 0.0624 (13) | 0.0658 (14) | −0.0029 (11) | 0.0086 (11) | 0.0073 (11) |
N5 | 0.0657 (15) | 0.0655 (14) | 0.0660 (15) | 0.0009 (11) | 0.0147 (12) | 0.0052 (12) |
N6 | 0.0579 (13) | 0.0655 (13) | 0.0596 (13) | −0.0053 (11) | 0.0100 (10) | −0.0012 (11) |
N7 | 0.0487 (13) | 0.0762 (14) | 0.0601 (13) | 0.0031 (11) | 0.0066 (10) | −0.0045 (11) |
N8 | 0.0490 (12) | 0.0505 (11) | 0.0616 (13) | −0.0002 (9) | 0.0125 (9) | −0.0088 (10) |
N9 | 0.0516 (13) | 0.0520 (11) | 0.0649 (14) | −0.0009 (10) | 0.0177 (10) | −0.0022 (10) |
N10 | 0.0577 (14) | 0.0641 (13) | 0.0709 (15) | 0.0001 (10) | 0.0224 (12) | −0.0141 (12) |
C1 | 0.111 (3) | 0.0763 (19) | 0.120 (3) | −0.0068 (18) | 0.034 (2) | −0.0250 (19) |
C2 | 0.083 (2) | 0.0597 (16) | 0.0675 (18) | −0.0029 (15) | 0.0146 (15) | 0.0025 (15) |
C3 | 0.089 (2) | 0.0701 (18) | 0.077 (2) | −0.0181 (17) | 0.0090 (17) | 0.0038 (16) |
C4 | 0.067 (2) | 0.087 (2) | 0.095 (2) | −0.0103 (17) | 0.0098 (17) | 0.0101 (19) |
C5 | 0.0647 (19) | 0.0756 (19) | 0.083 (2) | 0.0034 (15) | 0.0121 (15) | 0.0027 (16) |
C6 | 0.0576 (17) | 0.0607 (15) | 0.0605 (17) | 0.0055 (13) | 0.0041 (13) | 0.0062 (14) |
C8 | 0.0651 (17) | 0.0514 (14) | 0.0491 (15) | 0.0067 (13) | 0.0052 (12) | 0.0048 (12) |
C9 | 0.0733 (18) | 0.0556 (15) | 0.0471 (15) | 0.0050 (13) | 0.0043 (13) | 0.0054 (13) |
C10 | 0.084 (2) | 0.0656 (16) | 0.0604 (18) | 0.0096 (15) | 0.0085 (15) | −0.0031 (15) |
C11 | 0.118 (3) | 0.0689 (19) | 0.0572 (18) | 0.0135 (18) | 0.0048 (18) | −0.0092 (15) |
C12 | 0.117 (3) | 0.0604 (17) | 0.0619 (19) | −0.0095 (18) | −0.0127 (18) | −0.0020 (15) |
C13 | 0.083 (2) | 0.0611 (16) | 0.0659 (18) | −0.0066 (15) | −0.0032 (15) | 0.0072 (15) |
C14 | 0.0756 (18) | 0.0511 (15) | 0.0458 (15) | 0.0000 (13) | 0.0018 (13) | 0.0062 (12) |
C15 | 0.0615 (17) | 0.0534 (14) | 0.0495 (15) | −0.0034 (13) | 0.0026 (12) | 0.0098 (12) |
C16 | 0.0602 (17) | 0.0579 (16) | 0.0668 (19) | −0.0022 (14) | 0.0190 (14) | 0.0161 (15) |
C17 | 0.0656 (18) | 0.0762 (18) | 0.0728 (19) | 0.0049 (15) | 0.0170 (15) | 0.0187 (16) |
C18 | 0.081 (2) | 0.080 (2) | 0.093 (3) | 0.0165 (17) | 0.028 (2) | 0.0206 (19) |
C19 | 0.092 (2) | 0.0656 (18) | 0.091 (2) | 0.0093 (17) | 0.0402 (19) | 0.0082 (18) |
C20 | 0.078 (2) | 0.0701 (18) | 0.0670 (19) | −0.0059 (15) | 0.0252 (16) | 0.0057 (16) |
C22 | 0.111 (3) | 0.104 (2) | 0.085 (2) | −0.009 (2) | 0.025 (2) | −0.008 (2) |
C23 | 0.112 (3) | 0.0701 (18) | 0.105 (2) | −0.0201 (17) | 0.023 (2) | −0.0165 (18) |
C24 | 0.074 (2) | 0.0676 (17) | 0.0651 (18) | −0.0182 (15) | 0.0044 (15) | 0.0060 (15) |
C25 | 0.076 (2) | 0.084 (2) | 0.083 (2) | −0.0270 (17) | −0.0016 (17) | 0.0094 (18) |
C26 | 0.0547 (18) | 0.119 (3) | 0.088 (2) | −0.0240 (19) | 0.0036 (16) | 0.016 (2) |
C27 | 0.0510 (18) | 0.111 (2) | 0.0717 (19) | −0.0017 (16) | 0.0079 (14) | 0.0048 (18) |
C28 | 0.0481 (16) | 0.0789 (17) | 0.0543 (16) | −0.0012 (13) | 0.0051 (12) | 0.0062 (14) |
C30 | 0.0517 (16) | 0.0594 (14) | 0.0476 (15) | 0.0073 (12) | 0.0084 (12) | 0.0031 (12) |
C31 | 0.0582 (16) | 0.0536 (14) | 0.0451 (14) | 0.0070 (12) | 0.0060 (11) | −0.0003 (12) |
C32 | 0.0677 (17) | 0.0690 (17) | 0.0586 (16) | 0.0178 (14) | 0.0075 (13) | −0.0019 (14) |
C33 | 0.092 (2) | 0.0619 (17) | 0.0600 (18) | 0.0171 (16) | 0.0072 (15) | −0.0110 (14) |
C34 | 0.087 (2) | 0.0560 (15) | 0.0648 (18) | −0.0023 (14) | 0.0048 (15) | −0.0075 (14) |
C35 | 0.0693 (17) | 0.0566 (15) | 0.0554 (16) | −0.0023 (13) | 0.0072 (13) | −0.0013 (13) |
C36 | 0.0593 (16) | 0.0474 (13) | 0.0423 (13) | 0.0028 (12) | 0.0077 (11) | 0.0025 (11) |
C37 | 0.0539 (15) | 0.0491 (13) | 0.0474 (14) | 0.0000 (12) | 0.0109 (11) | 0.0054 (11) |
C38 | 0.0498 (15) | 0.0558 (15) | 0.0640 (17) | −0.0021 (12) | 0.0252 (13) | 0.0022 (13) |
C39 | 0.0546 (16) | 0.0675 (16) | 0.0721 (18) | 0.0041 (13) | 0.0242 (13) | 0.0054 (14) |
C40 | 0.069 (2) | 0.0733 (19) | 0.089 (2) | 0.0183 (15) | 0.0294 (17) | 0.0091 (17) |
C41 | 0.078 (2) | 0.0606 (16) | 0.089 (2) | 0.0081 (15) | 0.0376 (18) | −0.0078 (16) |
C42 | 0.0574 (17) | 0.0720 (17) | 0.080 (2) | −0.0023 (14) | 0.0288 (15) | −0.0166 (16) |
C44 | 0.083 (2) | 0.117 (2) | 0.108 (3) | 0.0049 (19) | 0.0197 (19) | −0.054 (2) |
N1—C6 | 1.340 (3) | C16—C17 | 1.380 (3) |
N1—C2 | 1.348 (3) | C17—C18 | 1.366 (3) |
N2—C8 | 1.289 (3) | C17—H17 | 0.930 |
N2—C6 | 1.399 (3) | C18—C19 | 1.368 (4) |
N3—C8 | 1.387 (3) | C18—H18 | 0.930 |
N3—C15 | 1.389 (3) | C19—C20 | 1.386 (4) |
N3—H3 | 0.860 | C19—H19 | 0.930 |
N4—C15 | 1.281 (3) | C20—C22 | 1.508 (4) |
N4—C16 | 1.408 (3) | C22—H22A | 0.960 |
N5—C16 | 1.343 (3) | C22—H22B | 0.960 |
N5—C20 | 1.351 (3) | C22—H22C | 0.960 |
N6—C24 | 1.346 (3) | C23—C24 | 1.503 (4) |
N6—C28 | 1.349 (3) | C23—H23A | 0.960 |
N7—C30 | 1.284 (3) | C23—H23B | 0.960 |
N7—C28 | 1.393 (3) | C23—H23C | 0.960 |
N8—C37 | 1.390 (3) | C24—C25 | 1.383 (4) |
N8—C30 | 1.392 (3) | C25—C26 | 1.366 (4) |
N8—H8 | 0.860 | C25—H25 | 0.930 |
N9—C37 | 1.279 (3) | C26—C27 | 1.372 (4) |
N9—C38 | 1.405 (3) | C26—H26 | 0.930 |
N10—C38 | 1.341 (3) | C27—C28 | 1.390 (3) |
N10—C42 | 1.349 (3) | C27—H27 | 0.930 |
C1—C2 | 1.487 (4) | C30—C31 | 1.472 (3) |
C1—H1A | 0.960 | C31—C36 | 1.380 (3) |
C1—H1B | 0.960 | C31—C32 | 1.383 (3) |
C1—H1C | 0.960 | C32—C33 | 1.384 (3) |
C2—C3 | 1.372 (4) | C32—H32 | 0.930 |
C3—C4 | 1.369 (4) | C33—C34 | 1.383 (3) |
C3—H3A | 0.930 | C33—H33 | 0.930 |
C4—C5 | 1.370 (4) | C34—C35 | 1.379 (3) |
C4—H4 | 0.930 | C34—H34 | 0.930 |
C5—C6 | 1.390 (3) | C35—C36 | 1.379 (3) |
C5—H5 | 0.930 | C35—H35 | 0.930 |
C8—C9 | 1.467 (3) | C36—C37 | 1.474 (3) |
C9—C14 | 1.387 (3) | C38—C39 | 1.386 (3) |
C9—C10 | 1.391 (3) | C39—C40 | 1.373 (3) |
C10—C11 | 1.377 (4) | C39—H39 | 0.930 |
C10—H10 | 0.930 | C40—C41 | 1.371 (4) |
C11—C12 | 1.383 (4) | C40—H40 | 0.930 |
C11—H11 | 0.930 | C41—C42 | 1.385 (4) |
C12—C13 | 1.393 (4) | C41—H41 | 0.930 |
C12—H12 | 0.930 | C42—C44 | 1.493 (4) |
C13—C14 | 1.377 (3) | C44—H44A | 0.960 |
C13—H13 | 0.930 | C44—H44B | 0.960 |
C14—C15 | 1.475 (3) | C44—H44C | 0.960 |
C6—N1—C2 | 118.0 (2) | C19—C20—C22 | 122.3 (3) |
C8—N2—C6 | 122.8 (2) | C20—C22—H22A | 109.5 |
C8—N3—C15 | 112.6 (2) | C20—C22—H22B | 109.5 |
C8—N3—H3 | 123.7 | H22A—C22—H22B | 109.5 |
C15—N3—H3 | 123.7 | C20—C22—H22C | 109.5 |
C15—N4—C16 | 122.1 (2) | H22A—C22—H22C | 109.5 |
C16—N5—C20 | 117.6 (2) | H22B—C22—H22C | 109.5 |
C24—N6—C28 | 118.5 (2) | C24—C23—H23A | 109.5 |
C30—N7—C28 | 123.0 (2) | C24—C23—H23B | 109.5 |
C37—N8—C30 | 112.13 (19) | H23A—C23—H23B | 109.5 |
C37—N8—H8 | 123.9 | C24—C23—H23C | 109.5 |
C30—N8—H8 | 123.9 | H23A—C23—H23C | 109.5 |
C37—N9—C38 | 121.9 (2) | H23B—C23—H23C | 109.5 |
C38—N10—C42 | 117.9 (2) | N6—C24—C25 | 121.7 (3) |
C2—C1—H1A | 109.5 | N6—C24—C23 | 116.7 (2) |
C2—C1—H1B | 109.5 | C25—C24—C23 | 121.6 (3) |
H1A—C1—H1B | 109.5 | C26—C25—C24 | 119.3 (3) |
C2—C1—H1C | 109.5 | C26—C25—H25 | 120.4 |
H1A—C1—H1C | 109.5 | C24—C25—H25 | 120.4 |
H1B—C1—H1C | 109.5 | C25—C26—C27 | 120.0 (3) |
N1—C2—C3 | 122.2 (2) | C25—C26—H26 | 120.0 |
N1—C2—C1 | 115.3 (3) | C27—C26—H26 | 120.0 |
C3—C2—C1 | 122.5 (3) | C26—C27—C28 | 118.4 (3) |
C4—C3—C2 | 119.4 (3) | C26—C27—H27 | 120.8 |
C4—C3—H3A | 120.3 | C28—C27—H27 | 120.8 |
C2—C3—H3A | 120.3 | N6—C28—C27 | 122.0 (3) |
C5—C4—C3 | 119.5 (3) | N6—C28—N7 | 121.0 (2) |
C5—C4—H4 | 120.3 | C27—C28—N7 | 117.0 (2) |
C3—C4—H4 | 120.3 | N7—C30—N8 | 130.5 (2) |
C4—C5—C6 | 118.6 (3) | N7—C30—C31 | 124.1 (2) |
C4—C5—H5 | 120.7 | N8—C30—C31 | 105.39 (19) |
C6—C5—H5 | 120.7 | C36—C31—C32 | 121.7 (2) |
N1—C6—C5 | 122.3 (2) | C36—C31—C30 | 108.54 (19) |
N1—C6—N2 | 120.8 (2) | C32—C31—C30 | 129.8 (2) |
C5—C6—N2 | 116.9 (2) | C31—C32—C33 | 116.7 (2) |
N2—C8—N3 | 131.0 (2) | C31—C32—H32 | 121.7 |
N2—C8—C9 | 123.5 (2) | C33—C32—H32 | 121.7 |
N3—C8—C9 | 105.5 (2) | C34—C33—C32 | 121.6 (2) |
C14—C9—C10 | 121.1 (2) | C34—C33—H33 | 119.2 |
C14—C9—C8 | 108.5 (2) | C32—C33—H33 | 119.2 |
C10—C9—C8 | 130.4 (2) | C35—C34—C33 | 121.2 (2) |
C11—C10—C9 | 117.6 (3) | C35—C34—H34 | 119.4 |
C11—C10—H10 | 121.2 | C33—C34—H34 | 119.4 |
C9—C10—H10 | 121.2 | C34—C35—C36 | 117.4 (2) |
C10—C11—C12 | 121.5 (3) | C34—C35—H35 | 121.3 |
C10—C11—H11 | 119.2 | C36—C35—H35 | 121.3 |
C12—C11—H11 | 119.2 | C35—C36—C31 | 121.4 (2) |
C11—C12—C13 | 120.8 (3) | C35—C36—C37 | 130.5 (2) |
C11—C12—H12 | 119.6 | C31—C36—C37 | 108.2 (2) |
C13—C12—H12 | 119.6 | N9—C37—N8 | 130.4 (2) |
C14—C13—C12 | 117.9 (3) | N9—C37—C36 | 123.8 (2) |
C14—C13—H13 | 121.1 | N8—C37—C36 | 105.58 (18) |
C12—C13—H13 | 121.1 | N10—C38—C39 | 122.7 (2) |
C13—C14—C9 | 121.1 (2) | N10—C38—N9 | 120.1 (2) |
C13—C14—C15 | 130.8 (3) | C39—C38—N9 | 117.1 (2) |
C9—C14—C15 | 108.1 (2) | C40—C39—C38 | 118.8 (3) |
N4—C15—N3 | 130.5 (2) | C40—C39—H39 | 120.6 |
N4—C15—C14 | 124.1 (2) | C38—C39—H39 | 120.6 |
N3—C15—C14 | 105.3 (2) | C39—C40—C41 | 119.1 (3) |
N5—C16—C17 | 123.0 (3) | C39—C40—H40 | 120.4 |
N5—C16—N4 | 118.7 (2) | C41—C40—H40 | 120.4 |
C17—C16—N4 | 118.1 (3) | C40—C41—C42 | 119.5 (3) |
C18—C17—C16 | 118.8 (3) | C40—C41—H41 | 120.2 |
C18—C17—H17 | 120.6 | C42—C41—H41 | 120.2 |
C16—C17—H17 | 120.6 | N10—C42—C41 | 121.8 (3) |
C17—C18—C19 | 119.4 (3) | N10—C42—C44 | 116.7 (3) |
C17—C18—H18 | 120.3 | C41—C42—C44 | 121.4 (3) |
C19—C18—H18 | 120.3 | C42—C44—H44A | 109.5 |
C18—C19—C20 | 119.5 (3) | C42—C44—H44B | 109.5 |
C18—C19—H19 | 120.3 | H44A—C44—H44B | 109.5 |
C20—C19—H19 | 120.3 | C42—C44—H44C | 109.5 |
N5—C20—C19 | 121.7 (3) | H44A—C44—H44C | 109.5 |
N5—C20—C22 | 116.0 (3) | H44B—C44—H44C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···N1 | 0.86 | 2.19 | 2.710 (3) | 119 |
N3—H3···N5 | 0.86 | 2.48 | 2.910 (3) | 112 |
N8—H8···N6 | 0.86 | 2.18 | 2.702 (3) | 118 |
N8—H8···N10 | 0.86 | 2.39 | 2.853 (3) | 114 |