Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804001813/cv6268sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804001813/cv6268Isup2.hkl |
CCDC reference: 234919
Data collection: P3 (Siemens,1989); cell refinement: P3; data reduction: XDISK (Siemens, 1991a); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1991b); software used to prepare material for publication: SHELXL97.
C42H30N2 | Z = 2 |
Mr = 562.68 | F(000) = 592 |
Triclinic, P1 | Dx = 1.238 Mg m−3 |
Hall symbol: -P 1 | Melting point: 118 K |
a = 8.830 (2) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.932 (2) Å | Cell parameters from 24 reflections |
c = 14.888 (3) Å | θ = 10–12° |
α = 90.94 (2)° | µ = 0.07 mm−1 |
β = 105.58 (2)° | T = 293 K |
γ = 92.12 (2)° | Needle, colourless |
V = 1509.4 (5) Å3 | 0.40 × 0.20 × 0.20 mm |
Siemens P3/PC diffractometer | Rint = 0.044 |
Radiation source: fine-focus sealed tube | θmax = 25.1°, θmin = 1.7° |
Graphite monochromator | h = 0→10 |
θ–2θ scans | k = −14→14 |
5672 measured reflections | l = −17→17 |
5298 independent reflections | 2 standard reflections every 98 reflections |
2469 reflections with I > 2σ(I) | intensity decay: 5% |
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)] = 0.052 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 0.96 | w = 1/[σ2(Fo2) + (0.0616P)2] where P = (Fo2 + 2Fc2)/3 |
5298 reflections | (Δ/σ)max < 0.001 |
397 parameters | Δρmax = 0.12 e Å−3 |
0 restraints | Δρmin = −0.16 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 | 0.5160 (2) | 0.66220 (15) | 0.77619 (13) | 0.0487 (5) | |
N2 | 0.1655 (2) | 0.74577 (15) | 0.80975 (14) | 0.0515 (5) | |
C1 | 0.6588 (3) | 0.68407 (19) | 0.84481 (16) | 0.0465 (6) | |
C2 | 0.7029 (3) | 0.7977 (2) | 0.84536 (17) | 0.0496 (6) | |
C3 | 0.8412 (3) | 0.8376 (2) | 0.90883 (19) | 0.0637 (8) | |
H3 | 0.8729 | 0.9129 | 0.9102 | 0.076* | |
C4 | 0.9302 (3) | 0.7650 (3) | 0.9693 (2) | 0.0684 (8) | |
H4 | 1.0225 | 0.7913 | 1.0121 | 0.082* | |
C5 | 0.8840 (3) | 0.6527 (2) | 0.96702 (19) | 0.0685 (8) | |
H5 | 0.9465 | 0.6046 | 1.0083 | 0.082* | |
C6 | 0.7475 (3) | 0.6105 (2) | 0.90514 (18) | 0.0596 (7) | |
H6 | 0.7165 | 0.5350 | 0.9042 | 0.072* | |
C7 | 0.4730 (3) | 0.76240 (19) | 0.73068 (17) | 0.0503 (6) | |
C8 | 0.5854 (3) | 0.84752 (19) | 0.77308 (17) | 0.0530 (7) | |
C9 | 0.5701 (4) | 0.9540 (2) | 0.7364 (2) | 0.0740 (9) | |
H9 | 0.6421 | 1.0118 | 0.7640 | 0.089* | |
C10 | 0.4497 (4) | 0.9740 (2) | 0.6601 (2) | 0.0866 (10) | |
H10 | 0.4399 | 1.0455 | 0.6358 | 0.104* | |
C11 | 0.3412 (4) | 0.8882 (2) | 0.6180 (2) | 0.0805 (9) | |
H11 | 0.2608 | 0.9035 | 0.5654 | 0.097* | |
C12 | 0.3499 (3) | 0.7813 (2) | 0.65242 (18) | 0.0615 (7) | |
H12 | 0.2768 | 0.7243 | 0.6245 | 0.074* | |
C13 | 0.2759 (3) | 0.7378 (2) | 0.89681 (17) | 0.0484 (6) | |
C14 | 0.3092 (3) | 0.8456 (2) | 0.93816 (18) | 0.0540 (7) | |
C15 | 0.4142 (3) | 0.8579 (3) | 1.0263 (2) | 0.0674 (8) | |
H15 | 0.4373 | 0.9284 | 1.0554 | 0.081* | |
C16 | 0.4837 (3) | 0.7650 (3) | 1.0703 (2) | 0.0741 (9) | |
H16 | 0.5563 | 0.7730 | 1.1285 | 0.089* | |
C17 | 0.4460 (3) | 0.6600 (3) | 1.0283 (2) | 0.0673 (8) | |
H17 | 0.4931 | 0.5981 | 1.0596 | 0.081* | |
C18 | 0.3410 (3) | 0.6438 (2) | 0.94182 (18) | 0.0591 (7) | |
H18 | 0.3149 | 0.5724 | 0.9148 | 0.071* | |
C19 | 0.1271 (3) | 0.85750 (19) | 0.79773 (18) | 0.0525 (7) | |
C20 | 0.2122 (3) | 0.9215 (2) | 0.87475 (18) | 0.0536 (7) | |
C21 | 0.1901 (4) | 1.0362 (2) | 0.8775 (2) | 0.0712 (8) | |
H21 | 0.2458 | 1.0806 | 0.9284 | 0.085* | |
C22 | 0.0847 (4) | 1.0828 (2) | 0.8039 (3) | 0.0832 (10) | |
H22 | 0.0689 | 1.1593 | 0.8055 | 0.100* | |
C23 | 0.0019 (4) | 1.0182 (2) | 0.7278 (2) | 0.0806 (9) | |
H23 | −0.0688 | 1.0519 | 0.6789 | 0.097* | |
C24 | 0.0221 (3) | 0.9038 (2) | 0.7228 (2) | 0.0659 (8) | |
H24 | −0.0327 | 0.8600 | 0.6712 | 0.079* | |
C25 | 0.4500 (3) | 0.55399 (19) | 0.74952 (16) | 0.0497 (6) | |
H25 | 0.5200 | 0.4981 | 0.7483 | 0.060* | |
C26 | 0.0840 (3) | 0.65840 (19) | 0.75022 (17) | 0.0529 (7) | |
H26 | −0.0247 | 0.6630 | 0.7296 | 0.063* | |
C27 | 0.2976 (3) | 0.52262 (18) | 0.72569 (15) | 0.0460 (6) | |
C28 | 0.1444 (3) | 0.56938 (18) | 0.71969 (16) | 0.0467 (6) | |
C29 | 0.0578 (3) | 0.46834 (17) | 0.66123 (16) | 0.0468 (6) | |
H29 | 0.0261 | 0.4882 | 0.5954 | 0.056* | |
C30 | 0.2216 (3) | 0.41000 (18) | 0.68271 (16) | 0.0468 (6) | |
H30 | 0.2281 | 0.3550 | 0.7316 | 0.056* | |
C31 | 0.2619 (3) | 0.35692 (19) | 0.60028 (17) | 0.0470 (6) | |
C32 | 0.3106 (3) | 0.4200 (2) | 0.53582 (19) | 0.0644 (8) | |
H32 | 0.3280 | 0.4971 | 0.5459 | 0.077* | |
C33 | 0.3342 (3) | 0.3704 (3) | 0.4562 (2) | 0.0774 (9) | |
H33 | 0.3671 | 0.4141 | 0.4133 | 0.093* | |
C34 | 0.3091 (3) | 0.2573 (3) | 0.4410 (2) | 0.0745 (9) | |
H34 | 0.3253 | 0.2238 | 0.3876 | 0.089* | |
C35 | 0.2604 (4) | 0.1933 (2) | 0.5038 (2) | 0.0726 (8) | |
H35 | 0.2434 | 0.1162 | 0.4934 | 0.087* | |
C36 | 0.2363 (3) | 0.2430 (2) | 0.58256 (18) | 0.0604 (7) | |
H36 | 0.2022 | 0.1988 | 0.6248 | 0.073* | |
C37 | −0.0756 (3) | 0.40386 (18) | 0.68415 (17) | 0.0453 (6) | |
C39 | −0.2969 (4) | 0.2726 (2) | 0.6361 (2) | 0.0817 (9) | |
H39 | −0.3657 | 0.2289 | 0.5892 | 0.098* | |
C40 | −0.3131 (3) | 0.2713 (2) | 0.7250 (3) | 0.0715 (8) | |
H40 | −0.3931 | 0.2277 | 0.7387 | 0.086* | |
C41 | −0.2108 (3) | 0.3348 (2) | 0.7930 (2) | 0.0694 (8) | |
H41 | −0.2199 | 0.3335 | 0.8537 | 0.083* | |
C42 | −0.0932 (3) | 0.4011 (2) | 0.77284 (19) | 0.0620 (7) | |
H42 | −0.0250 | 0.4446 | 0.8201 | 0.074* | |
C38 | −0.1786 (3) | 0.3385 (2) | 0.61564 (19) | 0.0668 (8) | |
H38 | −0.1687 | 0.3386 | 0.5550 | 0.080* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0495 (13) | 0.0440 (12) | 0.0485 (12) | −0.0040 (10) | 0.0073 (10) | −0.0013 (10) |
N2 | 0.0553 (13) | 0.0389 (12) | 0.0563 (13) | 0.0008 (10) | 0.0086 (11) | −0.0088 (10) |
C1 | 0.0478 (15) | 0.0496 (15) | 0.0409 (14) | −0.0023 (12) | 0.0105 (13) | −0.0015 (12) |
C2 | 0.0553 (17) | 0.0484 (15) | 0.0465 (15) | −0.0060 (13) | 0.0176 (13) | −0.0088 (12) |
C3 | 0.0684 (19) | 0.0610 (17) | 0.0598 (18) | −0.0202 (16) | 0.0183 (16) | −0.0183 (15) |
C4 | 0.0533 (18) | 0.082 (2) | 0.0635 (19) | −0.0075 (17) | 0.0067 (15) | −0.0113 (17) |
C5 | 0.0552 (18) | 0.080 (2) | 0.0644 (19) | 0.0001 (16) | 0.0056 (15) | −0.0001 (16) |
C6 | 0.0577 (17) | 0.0553 (16) | 0.0614 (18) | −0.0045 (14) | 0.0097 (15) | −0.0020 (14) |
C7 | 0.0576 (17) | 0.0446 (15) | 0.0496 (16) | 0.0022 (13) | 0.0161 (14) | 0.0015 (13) |
C8 | 0.0616 (18) | 0.0436 (15) | 0.0555 (16) | −0.0031 (13) | 0.0198 (14) | −0.0069 (13) |
C9 | 0.088 (2) | 0.0449 (17) | 0.087 (2) | −0.0061 (15) | 0.0212 (19) | −0.0005 (16) |
C10 | 0.099 (3) | 0.0509 (18) | 0.101 (3) | 0.0047 (18) | 0.010 (2) | 0.0172 (18) |
C11 | 0.084 (2) | 0.069 (2) | 0.080 (2) | 0.0088 (18) | 0.0058 (18) | 0.0220 (17) |
C12 | 0.0647 (19) | 0.0588 (18) | 0.0572 (17) | −0.0025 (14) | 0.0104 (15) | 0.0066 (14) |
C13 | 0.0446 (15) | 0.0495 (15) | 0.0523 (16) | 0.0002 (12) | 0.0158 (13) | −0.0012 (13) |
C14 | 0.0517 (16) | 0.0541 (16) | 0.0592 (18) | −0.0110 (13) | 0.0225 (14) | −0.0124 (14) |
C15 | 0.0631 (19) | 0.072 (2) | 0.0650 (19) | −0.0270 (16) | 0.0183 (16) | −0.0159 (16) |
C16 | 0.069 (2) | 0.094 (2) | 0.0549 (18) | −0.0216 (19) | 0.0108 (15) | 0.0068 (18) |
C17 | 0.0635 (19) | 0.078 (2) | 0.0602 (19) | −0.0056 (16) | 0.0178 (16) | 0.0127 (16) |
C18 | 0.0628 (18) | 0.0578 (17) | 0.0570 (17) | 0.0002 (14) | 0.0169 (15) | 0.0007 (14) |
C19 | 0.0516 (16) | 0.0385 (14) | 0.0685 (18) | 0.0027 (13) | 0.0181 (15) | −0.0058 (14) |
C20 | 0.0501 (16) | 0.0425 (15) | 0.0703 (18) | −0.0058 (13) | 0.0218 (14) | −0.0111 (14) |
C21 | 0.073 (2) | 0.0508 (18) | 0.094 (2) | −0.0071 (15) | 0.0317 (19) | −0.0155 (17) |
C22 | 0.090 (2) | 0.0415 (17) | 0.124 (3) | 0.0077 (17) | 0.039 (2) | −0.0053 (19) |
C23 | 0.077 (2) | 0.0542 (19) | 0.107 (3) | 0.0102 (16) | 0.0169 (19) | 0.0052 (18) |
C24 | 0.0612 (18) | 0.0502 (17) | 0.078 (2) | 0.0031 (14) | 0.0053 (16) | −0.0051 (15) |
C25 | 0.0521 (17) | 0.0432 (15) | 0.0504 (15) | −0.0011 (12) | 0.0083 (13) | 0.0018 (12) |
C26 | 0.0501 (16) | 0.0424 (14) | 0.0613 (17) | −0.0012 (12) | 0.0074 (13) | −0.0026 (13) |
C27 | 0.0497 (17) | 0.0397 (13) | 0.0451 (15) | −0.0013 (12) | 0.0071 (12) | 0.0003 (11) |
C28 | 0.0497 (15) | 0.0368 (13) | 0.0492 (15) | −0.0012 (12) | 0.0066 (12) | −0.0021 (11) |
C29 | 0.0523 (16) | 0.0387 (13) | 0.0456 (14) | 0.0009 (12) | 0.0068 (12) | −0.0011 (11) |
C30 | 0.0519 (15) | 0.0374 (13) | 0.0482 (15) | −0.0004 (11) | 0.0086 (12) | 0.0014 (11) |
C31 | 0.0454 (15) | 0.0424 (14) | 0.0512 (15) | 0.0011 (11) | 0.0097 (12) | −0.0013 (12) |
C32 | 0.073 (2) | 0.0548 (17) | 0.0679 (19) | −0.0080 (14) | 0.0243 (16) | −0.0042 (15) |
C33 | 0.073 (2) | 0.095 (2) | 0.067 (2) | −0.0156 (18) | 0.0279 (17) | −0.0076 (18) |
C34 | 0.0633 (19) | 0.097 (2) | 0.059 (2) | 0.0024 (17) | 0.0107 (16) | −0.0266 (19) |
C35 | 0.086 (2) | 0.0551 (18) | 0.068 (2) | 0.0097 (16) | 0.0049 (17) | −0.0167 (16) |
C36 | 0.075 (2) | 0.0431 (16) | 0.0605 (18) | 0.0028 (13) | 0.0129 (15) | −0.0021 (13) |
C37 | 0.0440 (15) | 0.0367 (13) | 0.0511 (16) | 0.0006 (11) | 0.0058 (12) | −0.0009 (11) |
C39 | 0.072 (2) | 0.069 (2) | 0.088 (3) | −0.0262 (17) | 0.0006 (19) | −0.0096 (17) |
C40 | 0.0556 (18) | 0.0548 (18) | 0.105 (3) | −0.0069 (14) | 0.0240 (19) | 0.0045 (18) |
C41 | 0.071 (2) | 0.0654 (18) | 0.077 (2) | −0.0054 (16) | 0.0296 (17) | −0.0007 (16) |
C42 | 0.0616 (18) | 0.0624 (17) | 0.0601 (19) | −0.0132 (14) | 0.0160 (15) | −0.0084 (14) |
C38 | 0.073 (2) | 0.0643 (17) | 0.0539 (17) | −0.0178 (16) | 0.0035 (15) | −0.0039 (14) |
N1—C7 | 1.398 (3) | C21—C22 | 1.373 (4) |
N1—C25 | 1.403 (3) | C21—H21 | 0.9300 |
N1—C1 | 1.406 (3) | C22—C23 | 1.377 (4) |
N2—C19 | 1.390 (3) | C22—H22 | 0.9300 |
N2—C26 | 1.400 (3) | C23—C24 | 1.387 (3) |
N2—C13 | 1.404 (3) | C23—H23 | 0.9300 |
C1—C6 | 1.375 (3) | C24—H24 | 0.9300 |
C1—C2 | 1.395 (3) | C25—C27 | 1.333 (3) |
C2—C3 | 1.391 (3) | C25—H25 | 0.9300 |
C2—C8 | 1.434 (3) | C26—C28 | 1.332 (3) |
C3—C4 | 1.369 (4) | C26—H26 | 0.9300 |
C3—H3 | 0.9300 | C27—C28 | 1.463 (3) |
C4—C5 | 1.383 (4) | C27—C30 | 1.530 (3) |
C4—H4 | 0.9300 | C28—C29 | 1.528 (3) |
C5—C6 | 1.378 (3) | C29—C37 | 1.500 (3) |
C5—H5 | 0.9300 | C29—C30 | 1.585 (3) |
C6—H6 | 0.9300 | C29—H29 | 0.9800 |
C7—C12 | 1.391 (3) | C30—C31 | 1.503 (3) |
C7—C8 | 1.408 (3) | C30—H30 | 0.9800 |
C8—C9 | 1.388 (3) | C31—C32 | 1.376 (3) |
C9—C10 | 1.363 (4) | C31—C36 | 1.379 (3) |
C9—H9 | 0.9300 | C32—C33 | 1.384 (4) |
C10—C11 | 1.394 (4) | C32—H32 | 0.9300 |
C10—H10 | 0.9300 | C33—C34 | 1.365 (4) |
C11—C12 | 1.381 (4) | C33—H33 | 0.9300 |
C11—H11 | 0.9300 | C34—C35 | 1.363 (4) |
C12—H12 | 0.9300 | C34—H34 | 0.9300 |
C13—C18 | 1.380 (3) | C35—C36 | 1.376 (3) |
C13—C14 | 1.402 (3) | C35—H35 | 0.9300 |
C14—C15 | 1.391 (3) | C36—H36 | 0.9300 |
C14—C20 | 1.448 (3) | C37—C42 | 1.371 (3) |
C15—C16 | 1.375 (4) | C37—C38 | 1.378 (3) |
C15—H15 | 0.9300 | C39—C40 | 1.369 (4) |
C16—C17 | 1.380 (4) | C39—C38 | 1.386 (4) |
C16—H16 | 0.9300 | C39—H39 | 0.9300 |
C17—C18 | 1.376 (3) | C40—C41 | 1.358 (4) |
C17—H17 | 0.9300 | C40—H40 | 0.9300 |
C18—H18 | 0.9300 | C41—C42 | 1.381 (3) |
C19—C24 | 1.383 (3) | C41—H41 | 0.9300 |
C19—C20 | 1.389 (3) | C42—H42 | 0.9300 |
C20—C21 | 1.391 (3) | C38—H38 | 0.9300 |
C7—N1—C25 | 127.7 (2) | C21—C22—C23 | 121.2 (3) |
C7—N1—C1 | 107.61 (18) | C21—C22—H22 | 119.4 |
C25—N1—C1 | 123.7 (2) | C23—C22—H22 | 119.4 |
C19—N2—C26 | 123.1 (2) | C22—C23—C24 | 121.1 (3) |
C19—N2—C13 | 107.95 (19) | C22—C23—H23 | 119.4 |
C26—N2—C13 | 128.1 (2) | C24—C23—H23 | 119.4 |
C6—C1—C2 | 122.1 (2) | C19—C24—C23 | 117.2 (3) |
C6—C1—N1 | 128.4 (2) | C19—C24—H24 | 121.4 |
C2—C1—N1 | 109.5 (2) | C23—C24—H24 | 121.4 |
C3—C2—C1 | 118.9 (2) | C27—C25—N1 | 127.1 (2) |
C3—C2—C8 | 134.3 (2) | C27—C25—H25 | 116.5 |
C1—C2—C8 | 106.7 (2) | N1—C25—H25 | 116.5 |
C4—C3—C2 | 119.4 (2) | C28—C26—N2 | 127.5 (2) |
C4—C3—H3 | 120.3 | C28—C26—H26 | 116.3 |
C2—C3—H3 | 120.3 | N2—C26—H26 | 116.3 |
C3—C4—C5 | 120.5 (3) | C25—C27—C28 | 139.9 (2) |
C3—C4—H4 | 119.8 | C25—C27—C30 | 127.8 (2) |
C5—C4—H4 | 119.8 | C28—C27—C30 | 92.11 (18) |
C6—C5—C4 | 121.6 (3) | C26—C28—C27 | 139.7 (2) |
C6—C5—H5 | 119.2 | C26—C28—C29 | 128.5 (2) |
C4—C5—H5 | 119.2 | C27—C28—C29 | 91.72 (17) |
C1—C6—C5 | 117.5 (2) | C37—C29—C28 | 123.0 (2) |
C1—C6—H6 | 121.2 | C37—C29—C30 | 116.77 (18) |
C5—C6—H6 | 121.2 | C28—C29—C30 | 87.61 (17) |
C12—C7—N1 | 129.3 (2) | C37—C29—H29 | 109.2 |
C12—C7—C8 | 122.1 (2) | C28—C29—H29 | 109.2 |
N1—C7—C8 | 108.5 (2) | C30—C29—H29 | 109.2 |
C9—C8—C7 | 118.6 (2) | C31—C30—C27 | 121.6 (2) |
C9—C8—C2 | 133.6 (2) | C31—C30—C29 | 115.92 (19) |
C7—C8—C2 | 107.7 (2) | C27—C30—C29 | 87.16 (16) |
C10—C9—C8 | 120.0 (3) | C31—C30—H30 | 110.0 |
C10—C9—H9 | 120.0 | C27—C30—H30 | 110.0 |
C8—C9—H9 | 120.0 | C29—C30—H30 | 110.0 |
C9—C10—C11 | 120.6 (3) | C32—C31—C36 | 117.8 (2) |
C9—C10—H10 | 119.7 | C32—C31—C30 | 121.9 (2) |
C11—C10—H10 | 119.7 | C36—C31—C30 | 120.0 (2) |
C12—C11—C10 | 121.6 (3) | C31—C32—C33 | 121.0 (3) |
C12—C11—H11 | 119.2 | C31—C32—H32 | 119.5 |
C10—C11—H11 | 119.2 | C33—C32—H32 | 119.5 |
C11—C12—C7 | 117.0 (3) | C34—C33—C32 | 119.9 (3) |
C11—C12—H12 | 121.5 | C34—C33—H33 | 120.1 |
C7—C12—H12 | 121.5 | C32—C33—H33 | 120.1 |
C18—C13—C14 | 122.1 (2) | C35—C34—C33 | 120.1 (3) |
C18—C13—N2 | 129.3 (2) | C35—C34—H34 | 119.9 |
C14—C13—N2 | 108.6 (2) | C33—C34—H34 | 119.9 |
C15—C14—C13 | 118.7 (3) | C34—C35—C36 | 119.8 (3) |
C15—C14—C20 | 134.3 (2) | C34—C35—H35 | 120.1 |
C13—C14—C20 | 106.9 (2) | C36—C35—H35 | 120.1 |
C16—C15—C14 | 119.5 (3) | C35—C36—C31 | 121.4 (3) |
C16—C15—H15 | 120.2 | C35—C36—H36 | 119.3 |
C14—C15—H15 | 120.2 | C31—C36—H36 | 119.3 |
C15—C16—C17 | 120.2 (3) | C42—C37—C38 | 118.1 (2) |
C15—C16—H16 | 119.9 | C42—C37—C29 | 122.4 (2) |
C17—C16—H16 | 119.9 | C38—C37—C29 | 119.4 (2) |
C18—C17—C16 | 122.2 (3) | C40—C39—C38 | 120.4 (3) |
C18—C17—H17 | 118.9 | C40—C39—H39 | 119.8 |
C16—C17—H17 | 118.9 | C38—C39—H39 | 119.8 |
C17—C18—C13 | 117.3 (3) | C41—C40—C39 | 119.1 (3) |
C17—C18—H18 | 121.4 | C41—C40—H40 | 120.5 |
C13—C18—H18 | 121.4 | C39—C40—H40 | 120.5 |
C24—C19—C20 | 122.4 (2) | C40—C41—C42 | 120.8 (3) |
C24—C19—N2 | 128.0 (2) | C40—C41—H41 | 119.6 |
C20—C19—N2 | 109.6 (2) | C42—C41—H41 | 119.6 |
C19—C20—C21 | 119.0 (3) | C37—C42—C41 | 121.0 (2) |
C19—C20—C14 | 107.0 (2) | C37—C42—H42 | 119.5 |
C21—C20—C14 | 134.0 (3) | C41—C42—H42 | 119.5 |
C22—C21—C20 | 119.0 (3) | C37—C38—C39 | 120.7 (3) |
C22—C21—H21 | 120.5 | C37—C38—H38 | 119.7 |
C20—C21—H21 | 120.5 | C39—C38—H38 | 119.7 |
C7—N1—C1—C6 | −178.3 (2) | C13—C14—C20—C19 | −1.0 (3) |
C25—N1—C1—C6 | −9.1 (4) | C15—C14—C20—C21 | 1.6 (5) |
C7—N1—C1—C2 | 2.3 (3) | C13—C14—C20—C21 | 178.3 (3) |
C25—N1—C1—C2 | 171.5 (2) | C19—C20—C21—C22 | −0.1 (4) |
C6—C1—C2—C3 | 0.2 (4) | C14—C20—C21—C22 | −179.2 (3) |
N1—C1—C2—C3 | 179.6 (2) | C20—C21—C22—C23 | −0.3 (5) |
C6—C1—C2—C8 | 179.1 (2) | C21—C22—C23—C24 | 0.0 (5) |
N1—C1—C2—C8 | −1.4 (3) | C20—C19—C24—C23 | −1.2 (4) |
C1—C2—C3—C4 | −0.2 (4) | N2—C19—C24—C23 | 178.9 (2) |
C8—C2—C3—C4 | −178.8 (3) | C22—C23—C24—C19 | 0.8 (4) |
C2—C3—C4—C5 | 0.4 (4) | C7—N1—C25—C27 | −49.4 (4) |
C3—C4—C5—C6 | −0.5 (4) | C1—N1—C25—C27 | 143.6 (2) |
C2—C1—C6—C5 | −0.3 (4) | C19—N2—C26—C28 | 140.4 (3) |
N1—C1—C6—C5 | −179.6 (2) | C13—N2—C26—C28 | −51.5 (4) |
C4—C5—C6—C1 | 0.5 (4) | N1—C25—C27—C28 | −3.9 (5) |
C25—N1—C7—C12 | 4.5 (4) | N1—C25—C27—C30 | 170.0 (2) |
C1—N1—C7—C12 | 173.2 (2) | N2—C26—C28—C27 | −2.7 (5) |
C25—N1—C7—C8 | −170.9 (2) | N2—C26—C28—C29 | 174.6 (2) |
C1—N1—C7—C8 | −2.2 (3) | C25—C27—C28—C26 | −16.1 (6) |
C12—C7—C8—C9 | 1.4 (4) | C30—C27—C28—C26 | 168.6 (3) |
N1—C7—C8—C9 | 177.3 (2) | C25—C27—C28—C29 | 166.0 (3) |
C12—C7—C8—C2 | −174.5 (2) | C30—C27—C28—C29 | −9.26 (18) |
N1—C7—C8—C2 | 1.4 (3) | C26—C28—C29—C37 | −48.6 (4) |
C3—C2—C8—C9 | 3.7 (5) | C27—C28—C29—C37 | 129.6 (2) |
C1—C2—C8—C9 | −175.0 (3) | C26—C28—C29—C30 | −169.3 (3) |
C3—C2—C8—C7 | 178.8 (3) | C27—C28—C29—C30 | 8.93 (17) |
C1—C2—C8—C7 | 0.0 (3) | C25—C27—C30—C31 | −48.3 (3) |
C7—C8—C9—C10 | −1.1 (4) | C28—C27—C30—C31 | 127.8 (2) |
C2—C8—C9—C10 | 173.6 (3) | C25—C27—C30—C29 | −167.2 (2) |
C8—C9—C10—C11 | −0.1 (5) | C28—C27—C30—C29 | 8.93 (17) |
C9—C10—C11—C12 | 0.9 (5) | C37—C29—C30—C31 | 101.3 (2) |
C10—C11—C12—C7 | −0.6 (4) | C28—C29—C30—C31 | −132.6 (2) |
N1—C7—C12—C11 | −175.5 (3) | C37—C29—C30—C27 | −134.6 (2) |
C8—C7—C12—C11 | −0.6 (4) | C28—C29—C30—C27 | −8.55 (17) |
C19—N2—C13—C18 | 175.4 (2) | C27—C30—C31—C32 | −28.2 (3) |
C26—N2—C13—C18 | 5.8 (4) | C29—C30—C31—C32 | 75.4 (3) |
C19—N2—C13—C14 | −1.4 (3) | C27—C30—C31—C36 | 158.0 (2) |
C26—N2—C13—C14 | −171.0 (2) | C29—C30—C31—C36 | −98.5 (3) |
C18—C13—C14—C15 | 1.7 (4) | C36—C31—C32—C33 | −0.4 (4) |
N2—C13—C14—C15 | 178.8 (2) | C30—C31—C32—C33 | −174.4 (2) |
C18—C13—C14—C20 | −175.6 (2) | C31—C32—C33—C34 | −0.1 (4) |
N2—C13—C14—C20 | 1.5 (3) | C32—C33—C34—C35 | 0.2 (4) |
C13—C14—C15—C16 | 0.6 (4) | C33—C34—C35—C36 | 0.1 (4) |
C20—C14—C15—C16 | 177.0 (3) | C34—C35—C36—C31 | −0.6 (4) |
C14—C15—C16—C17 | −1.8 (4) | C32—C31—C36—C35 | 0.7 (4) |
C15—C16—C17—C18 | 0.9 (4) | C30—C31—C36—C35 | 174.9 (2) |
C16—C17—C18—C13 | 1.3 (4) | C28—C29—C37—C42 | −24.8 (3) |
C14—C13—C18—C17 | −2.6 (4) | C30—C29—C37—C42 | 81.0 (3) |
N2—C13—C18—C17 | −179.0 (2) | C28—C29—C37—C38 | 159.8 (2) |
C26—N2—C19—C24 | −9.1 (4) | C30—C29—C37—C38 | −94.4 (3) |
C13—N2—C19—C24 | −179.3 (2) | C38—C39—C40—C41 | −0.6 (4) |
C26—N2—C19—C20 | 171.0 (2) | C39—C40—C41—C42 | 1.0 (4) |
C13—N2—C19—C20 | 0.8 (3) | C38—C37—C42—C41 | 0.0 (4) |
C24—C19—C20—C21 | 0.8 (4) | C29—C37—C42—C41 | −175.4 (2) |
N2—C19—C20—C21 | −179.3 (2) | C40—C41—C42—C37 | −0.7 (4) |
C24—C19—C20—C14 | −179.8 (2) | C42—C37—C38—C39 | 0.3 (4) |
N2—C19—C20—C14 | 0.1 (3) | C29—C37—C38—C39 | 175.9 (2) |
C15—C14—C20—C19 | −177.7 (3) | C40—C39—C38—C37 | 0.0 (4) |