Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805007142/bt6618sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805007142/bt66183sup2.hkl |
CCDC reference: 270239
Data collection: P3 (Siemens, 1989); cell refinement: P3; data reduction: XDISK (Siemens, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
2C30H18·3C12H4N4 | Z = 1 |
Mr = 1369.46 | F(000) = 708 |
Triclinic, P1 | Dx = 1.290 Mg m−3 |
a = 9.589 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.617 (5) Å | Cell parameters from 25 reflections |
c = 21.952 (12) Å | θ = 10–11.5° |
α = 80.81 (3)° | µ = 0.08 mm−1 |
β = 80.64 (4)° | T = 173 K |
γ = 62.50 (4)° | Plate, dark blue–violet |
V = 1763.4 (16) Å3 | 0.7 × 0.7 × 0.1 mm |
Siemens R3 diffractometer | Rint = 0.050 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 3.2° |
Graphite monochromator | h = −11→9 |
ω scans | k = −11→9 |
9928 measured reflections | l = −26→26 |
6211 independent reflections | 3 standard reflections every 147 reflections |
2764 reflections with I > 2σ(I) | intensity decay: none |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.157 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0588P)2] where P = (Fo2 + 2Fc2)/3 |
6211 reflections | (Δ/σ)max < 0.001 |
487 parameters | Δρmax = 0.22 e Å−3 |
461 restraints | Δρmin = −0.25 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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 6.2208 (0.0102) x + 3.0831 (0.0116) y + 5.6276 (0.0269) z = 3.8141 (0.0269) * -0.0047 (0.0021) C13 * 0.0018 (0.0022) C14 * 0.0030 (0.0023) C15 * -0.0050 (0.0024) C16 * 0.0021 (0.0023) C17 * 0.0028 (0.0022) C18 Rms deviation of fitted atoms = 0.0034 - 6.3838 (0.0057) x + 3.0427 (0.0042) y + 4.4737 (0.0158) z = 2.4542 (0.0105) Angle to previous plane (with approximate e.s.d.) = 3.10 (0.18) * -0.0319 (0.0025) C1 * -0.0407 (0.0026) C2 * -0.0036 (0.0026) C3 * 0.0207 (0.0026) C4 * 0.0158 (0.0024) C5 * -0.0176 (0.0025) C6 * -0.0372 (0.0026) C7 * -0.0178 (0.0025) C8 * 0.0517 (0.0023) C9 * 0.0091 (0.0026) C1A * 0.0205 (0.0026) C4A * 0.0189 (0.0026) C5A * 0.0121 (0.0025) C8A Rms deviation of fitted atoms = 0.0264 - 3.6952 (0.0135) x + 5.8249 (0.0120) y + 6.2196 (0.0297) z = 4.4691 (0.0290) Angle to previous plane (with approximate e.s.d.) = 19.21 (0.17) * 0.0075 (0.0023) C13' * -0.0118 (0.0025) C14' * 0.0059 (0.0027) C15' * 0.0043 (0.0030) C16' * -0.0086 (0.0028) C17' * 0.0027 (0.0024) C18' Rms deviation of fitted atoms = 0.0074 |
x | y | z | Uiso*/Ueq | ||
C1 | 0.0693 (3) | −0.1150 (4) | 0.71856 (14) | 0.0414 (8) | |
H1 | 0.0850 | −0.1514 | 0.7609 | 0.050* | |
C1A | 0.1018 (3) | 0.0082 (3) | 0.69025 (13) | 0.0338 (7) | |
C2 | 0.0134 (4) | −0.1843 (4) | 0.68398 (15) | 0.0478 (9) | |
H2 | −0.0086 | −0.2690 | 0.7030 | 0.057* | |
C3 | −0.0110 (4) | −0.1320 (4) | 0.62183 (16) | 0.0513 (9) | |
H3 | −0.0509 | −0.1794 | 0.5990 | 0.062* | |
C4 | 0.0234 (4) | −0.0102 (4) | 0.59356 (14) | 0.0437 (8) | |
H4 | 0.0081 | 0.0256 | 0.5511 | 0.052* | |
C4A | 0.0802 (3) | 0.0590 (3) | 0.62750 (13) | 0.0348 (7) | |
C5 | 0.1291 (3) | 0.2716 (4) | 0.55156 (13) | 0.0404 (8) | |
H5 | 0.0933 | 0.2541 | 0.5170 | 0.048* | |
C5A | 0.1273 (3) | 0.1850 (3) | 0.60861 (13) | 0.0326 (7) | |
C6 | 0.1841 (4) | 0.3842 (4) | 0.54607 (14) | 0.0443 (8) | |
H6 | 0.1868 | 0.4437 | 0.5073 | 0.053* | |
C7 | 0.2349 (4) | 0.4100 (4) | 0.59666 (14) | 0.0466 (9) | |
H7 | 0.2727 | 0.4870 | 0.5921 | 0.056* | |
C8 | 0.2320 (4) | 0.3263 (4) | 0.65379 (14) | 0.0433 (8) | |
H8 | 0.2667 | 0.3462 | 0.6881 | 0.052* | |
C8A | 0.1782 (3) | 0.2133 (3) | 0.66048 (12) | 0.0344 (7) | |
C9 | 0.1583 (3) | 0.1061 (3) | 0.71379 (12) | 0.0339 (7) | |
C10 | 0.1817 (3) | 0.1050 (3) | 0.77377 (13) | 0.0364 (8) | |
C11 | 0.2335 (3) | 0.2073 (4) | 0.79404 (13) | 0.0378 (8) | |
C12 | 0.2768 (4) | 0.2846 (4) | 0.81691 (13) | 0.0388 (8) | |
C13 | 0.3345 (3) | 0.3744 (4) | 0.84159 (13) | 0.0376 (8) | |
C14 | 0.3598 (4) | 0.4950 (4) | 0.80468 (15) | 0.0462 (8) | |
H14 | 0.3341 | 0.5202 | 0.7630 | 0.055* | |
C15 | 0.4215 (4) | 0.5778 (4) | 0.82762 (17) | 0.0535 (9) | |
H15 | 0.4380 | 0.6597 | 0.8022 | 0.064* | |
C16 | 0.4589 (4) | 0.5400 (4) | 0.88830 (18) | 0.0606 (10) | |
H16 | 0.5027 | 0.5956 | 0.9044 | 0.073* | |
C17 | 0.4335 (4) | 0.4231 (4) | 0.92557 (16) | 0.0552 (10) | |
H17 | 0.4589 | 0.3996 | 0.9672 | 0.066* | |
C18 | 0.3716 (4) | 0.3392 (4) | 0.90319 (14) | 0.0482 (9) | |
H18 | 0.3543 | 0.2586 | 0.9292 | 0.058* | |
C11' | 0.1539 (4) | 0.0028 (4) | 0.82435 (14) | 0.0415 (8) | |
C12' | 0.1306 (4) | −0.0710 (4) | 0.87059 (14) | 0.0435 (8) | |
C13' | 0.0991 (4) | −0.1572 (4) | 0.92590 (13) | 0.0436 (8) | |
C14' | −0.0008 (4) | −0.2258 (4) | 0.92764 (15) | 0.0573 (10) | |
H14' | −0.0458 | −0.2198 | 0.8913 | 0.069* | |
C15' | −0.0350 (5) | −0.3029 (5) | 0.98236 (18) | 0.0743 (12) | |
H15' | −0.1061 | −0.3471 | 0.9837 | 0.089* | |
C16' | 0.0334 (5) | −0.3160 (5) | 1.03499 (18) | 0.0804 (14) | |
H16' | 0.0102 | −0.3694 | 1.0725 | 0.096* | |
C17' | 0.1353 (5) | −0.2509 (5) | 1.03254 (16) | 0.0786 (13) | |
H17' | 0.1839 | −0.2615 | 1.0686 | 0.094* | |
C18' | 0.1686 (4) | −0.1707 (4) | 0.97900 (14) | 0.0596 (10) | |
H18' | 0.2381 | −0.1250 | 0.9782 | 0.071* | |
C19 | 0.3879 (4) | 1.0804 (4) | 0.14087 (15) | 0.0469 (9) | |
C20 | 0.3729 (3) | 1.0196 (4) | 0.20428 (13) | 0.0389 (8) | |
C21 | 0.4173 (4) | 1.0841 (4) | 0.24802 (14) | 0.0402 (8) | |
C22 | 0.3222 (3) | 0.9047 (3) | 0.22244 (13) | 0.0354 (7) | |
C23 | 0.2690 (3) | 0.8468 (4) | 0.17949 (13) | 0.0374 (8) | |
H23 | 0.2648 | 0.8905 | 0.1374 | 0.045* | |
C24 | 0.2250 (3) | 0.7320 (3) | 0.19777 (13) | 0.0375 (8) | |
H24 | 0.1883 | 0.6972 | 0.1684 | 0.045* | |
C25 | 0.2318 (3) | 0.6594 (3) | 0.26086 (13) | 0.0350 (7) | |
C26 | 0.2810 (3) | 0.7199 (4) | 0.30435 (13) | 0.0385 (8) | |
H26 | 0.2833 | 0.6773 | 0.3465 | 0.046* | |
C27 | 0.3239 (3) | 0.8361 (4) | 0.28627 (13) | 0.0370 (8) | |
H27 | 0.3561 | 0.8742 | 0.3160 | 0.044* | |
C28 | 0.1929 (4) | 0.4610 (4) | 0.33948 (15) | 0.0416 (8) | |
C29 | 0.1930 (3) | 0.5366 (4) | 0.27746 (13) | 0.0375 (8) | |
C30 | 0.1505 (4) | 0.4739 (4) | 0.23216 (14) | 0.0422 (8) | |
N1 | 0.4043 (4) | 1.1277 (4) | 0.09029 (13) | 0.0679 (9) | |
N2 | 0.4512 (3) | 1.1363 (3) | 0.28354 (12) | 0.0527 (8) | |
N3 | 0.1919 (3) | 0.3985 (3) | 0.38818 (12) | 0.0513 (8) | |
N4 | 0.1185 (3) | 0.4205 (3) | 0.19628 (13) | 0.0575 (8) | |
C31 | 0.3562 (4) | 0.6999 (4) | 0.49761 (14) | 0.0408 (8) | |
C32 | 0.4116 (3) | 0.7586 (3) | 0.53950 (12) | 0.0341 (7) | |
C33 | 0.4208 (3) | 0.6846 (3) | 0.60195 (14) | 0.0371 (8) | |
C34 | 0.4448 (3) | 0.9498 (3) | 0.45696 (12) | 0.0342 (7) | |
H34 | 0.4065 | 0.9148 | 0.4283 | 0.041* | |
C35 | 0.4540 (3) | 0.8781 (3) | 0.52011 (12) | 0.0332 (7) | |
C36 | 0.5112 (3) | 0.9358 (3) | 0.56225 (13) | 0.0365 (8) | |
H36 | 0.5177 | 0.8920 | 0.6043 | 0.044* | |
N5 | 0.3110 (4) | 0.6549 (3) | 0.46327 (12) | 0.0583 (8) | |
N6 | 0.4282 (3) | 0.6228 (3) | 0.65118 (12) | 0.0489 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0380 (19) | 0.043 (2) | 0.0383 (17) | −0.0156 (16) | −0.0007 (14) | −0.0011 (15) |
C1A | 0.0283 (17) | 0.0334 (18) | 0.0383 (17) | −0.0124 (14) | −0.0039 (13) | −0.0038 (14) |
C2 | 0.050 (2) | 0.041 (2) | 0.057 (2) | −0.0270 (17) | 0.0045 (17) | −0.0062 (17) |
C3 | 0.051 (2) | 0.052 (2) | 0.058 (2) | −0.0255 (19) | −0.0007 (17) | −0.0194 (18) |
C4 | 0.045 (2) | 0.049 (2) | 0.0370 (17) | −0.0199 (17) | −0.0019 (15) | −0.0087 (15) |
C4A | 0.0319 (18) | 0.0347 (18) | 0.0351 (17) | −0.0129 (15) | 0.0005 (13) | −0.0059 (14) |
C5 | 0.0376 (19) | 0.046 (2) | 0.0300 (17) | −0.0124 (16) | −0.0050 (14) | −0.0032 (15) |
C5A | 0.0279 (17) | 0.0324 (18) | 0.0337 (16) | −0.0118 (14) | 0.0012 (13) | −0.0028 (13) |
C6 | 0.047 (2) | 0.044 (2) | 0.0369 (18) | −0.0209 (17) | 0.0023 (15) | 0.0041 (15) |
C7 | 0.055 (2) | 0.053 (2) | 0.0401 (19) | −0.0340 (18) | 0.0031 (16) | −0.0012 (16) |
C8 | 0.046 (2) | 0.050 (2) | 0.0383 (18) | −0.0257 (17) | −0.0018 (15) | −0.0028 (15) |
C8A | 0.0306 (17) | 0.0382 (19) | 0.0308 (16) | −0.0132 (15) | −0.0004 (13) | −0.0028 (14) |
C9 | 0.0273 (17) | 0.0359 (18) | 0.0342 (16) | −0.0114 (14) | −0.0023 (13) | −0.0010 (13) |
C10 | 0.0324 (18) | 0.0377 (19) | 0.0349 (17) | −0.0135 (15) | −0.0026 (13) | 0.0004 (14) |
C11 | 0.0339 (19) | 0.042 (2) | 0.0318 (17) | −0.0139 (15) | −0.0025 (13) | −0.0005 (14) |
C12 | 0.0367 (19) | 0.042 (2) | 0.0333 (17) | −0.0148 (16) | −0.0010 (14) | −0.0036 (15) |
C13 | 0.0347 (18) | 0.0397 (19) | 0.0364 (17) | −0.0146 (15) | −0.0014 (14) | −0.0070 (14) |
C14 | 0.044 (2) | 0.041 (2) | 0.0438 (19) | −0.0130 (16) | 0.0022 (15) | −0.0045 (16) |
C15 | 0.047 (2) | 0.036 (2) | 0.071 (2) | −0.0164 (17) | 0.0073 (18) | −0.0099 (18) |
C16 | 0.049 (2) | 0.061 (3) | 0.078 (3) | −0.026 (2) | 0.002 (2) | −0.028 (2) |
C17 | 0.053 (2) | 0.068 (3) | 0.044 (2) | −0.022 (2) | −0.0019 (17) | −0.0224 (18) |
C18 | 0.049 (2) | 0.055 (2) | 0.0388 (19) | −0.0229 (18) | 0.0046 (16) | −0.0121 (17) |
C11' | 0.0407 (19) | 0.040 (2) | 0.0372 (17) | −0.0131 (16) | −0.0058 (14) | 0.0011 (15) |
C12' | 0.042 (2) | 0.043 (2) | 0.0395 (18) | −0.0147 (16) | −0.0062 (15) | 0.0002 (15) |
C13' | 0.048 (2) | 0.037 (2) | 0.0332 (17) | −0.0108 (16) | −0.0005 (15) | 0.0002 (14) |
C14' | 0.054 (2) | 0.059 (2) | 0.051 (2) | −0.024 (2) | −0.0067 (17) | 0.0132 (18) |
C15' | 0.067 (3) | 0.078 (3) | 0.074 (3) | −0.040 (2) | 0.005 (2) | 0.017 (2) |
C16' | 0.096 (4) | 0.076 (3) | 0.046 (2) | −0.031 (3) | 0.013 (2) | 0.012 (2) |
C17' | 0.110 (4) | 0.083 (3) | 0.031 (2) | −0.037 (3) | −0.003 (2) | 0.000 (2) |
C18' | 0.077 (3) | 0.059 (2) | 0.0368 (19) | −0.026 (2) | −0.0065 (18) | −0.0032 (17) |
C19 | 0.045 (2) | 0.049 (2) | 0.047 (2) | −0.0212 (17) | −0.0043 (16) | −0.0020 (17) |
C20 | 0.040 (2) | 0.039 (2) | 0.0352 (17) | −0.0144 (16) | −0.0035 (14) | −0.0058 (14) |
C21 | 0.0366 (19) | 0.039 (2) | 0.0405 (18) | −0.0146 (16) | −0.0008 (15) | −0.0040 (15) |
C22 | 0.0303 (18) | 0.0312 (18) | 0.0350 (17) | −0.0060 (14) | −0.0026 (14) | −0.0025 (14) |
C23 | 0.0371 (19) | 0.041 (2) | 0.0312 (16) | −0.0160 (16) | −0.0011 (14) | −0.0027 (14) |
C24 | 0.0355 (19) | 0.041 (2) | 0.0337 (17) | −0.0143 (15) | −0.0070 (14) | −0.0017 (14) |
C25 | 0.0270 (17) | 0.0363 (19) | 0.0337 (16) | −0.0077 (14) | −0.0026 (13) | −0.0032 (14) |
C26 | 0.0375 (19) | 0.0394 (19) | 0.0311 (16) | −0.0115 (15) | −0.0037 (14) | −0.0017 (14) |
C27 | 0.0374 (19) | 0.0402 (19) | 0.0301 (16) | −0.0127 (15) | −0.0051 (13) | −0.0075 (14) |
C28 | 0.041 (2) | 0.0344 (19) | 0.0426 (19) | −0.0109 (16) | −0.0033 (15) | −0.0036 (15) |
C29 | 0.0341 (18) | 0.0375 (19) | 0.0349 (17) | −0.0127 (15) | −0.0010 (14) | −0.0004 (14) |
C30 | 0.042 (2) | 0.039 (2) | 0.0399 (18) | −0.0156 (16) | −0.0046 (15) | 0.0048 (16) |
N1 | 0.084 (2) | 0.078 (2) | 0.0487 (19) | −0.046 (2) | −0.0059 (17) | 0.0056 (17) |
N2 | 0.057 (2) | 0.0517 (19) | 0.0485 (17) | −0.0220 (16) | −0.0089 (14) | −0.0081 (15) |
N3 | 0.0573 (19) | 0.0487 (18) | 0.0401 (16) | −0.0203 (15) | −0.0014 (13) | 0.0024 (14) |
N4 | 0.068 (2) | 0.057 (2) | 0.0525 (18) | −0.0300 (17) | −0.0186 (16) | 0.0000 (15) |
C31 | 0.044 (2) | 0.040 (2) | 0.0372 (18) | −0.0209 (16) | −0.0039 (15) | 0.0065 (15) |
C32 | 0.0374 (18) | 0.0321 (18) | 0.0297 (16) | −0.0145 (15) | −0.0013 (13) | 0.0004 (13) |
C33 | 0.0380 (19) | 0.0347 (19) | 0.0369 (18) | −0.0169 (15) | −0.0028 (14) | 0.0024 (15) |
C34 | 0.0420 (19) | 0.0322 (18) | 0.0293 (16) | −0.0177 (15) | −0.0044 (13) | −0.0014 (13) |
C35 | 0.0319 (17) | 0.0290 (17) | 0.0322 (16) | −0.0099 (14) | −0.0016 (13) | 0.0007 (13) |
C36 | 0.0418 (19) | 0.0366 (19) | 0.0274 (16) | −0.0160 (16) | −0.0030 (14) | 0.0013 (14) |
N5 | 0.082 (2) | 0.061 (2) | 0.0447 (17) | −0.0440 (18) | −0.0137 (16) | 0.0035 (15) |
N6 | 0.0580 (19) | 0.0476 (18) | 0.0411 (16) | −0.0272 (15) | −0.0024 (13) | 0.0049 (14) |
C1—C1A | 1.390 (4) | C13'—C14' | 1.385 (4) |
C1—C2 | 1.390 (4) | C13'—C18' | 1.394 (4) |
C1—H1 | 0.9500 | C14'—C15' | 1.383 (4) |
C1A—C4A | 1.401 (4) | C14'—H14' | 0.9500 |
C1A—C9 | 1.471 (4) | C15'—C16' | 1.380 (5) |
C2—C3 | 1.395 (4) | C15'—H15' | 0.9500 |
C2—H2 | 0.9500 | C16'—C17' | 1.373 (5) |
C3—C4 | 1.387 (4) | C16'—H16' | 0.9500 |
C3—H3 | 0.9500 | C17'—C18' | 1.376 (5) |
C4—C4A | 1.385 (4) | C17'—H17' | 0.9500 |
C4—H4 | 0.9500 | C18'—H18' | 0.9500 |
C4A—C5A | 1.459 (4) | C19—N1 | 1.146 (4) |
C5—C6 | 1.389 (4) | C19—C20 | 1.433 (4) |
C5—C5A | 1.391 (4) | C20—C22 | 1.381 (4) |
C5—H5 | 0.9500 | C20—C21 | 1.433 (4) |
C5A—C8A | 1.418 (4) | C21—N2 | 1.151 (4) |
C6—C7 | 1.382 (4) | C22—C23 | 1.431 (4) |
C6—H6 | 0.9500 | C22—C27 | 1.450 (4) |
C7—C8 | 1.382 (4) | C23—C24 | 1.339 (4) |
C7—H7 | 0.9500 | C23—H23 | 0.9500 |
C8—C8A | 1.383 (4) | C24—C25 | 1.445 (4) |
C8—H8 | 0.9500 | C24—H24 | 0.9500 |
C8A—C9 | 1.481 (4) | C25—C29 | 1.374 (4) |
C9—C10 | 1.369 (4) | C25—C26 | 1.432 (4) |
C10—C11' | 1.437 (4) | C26—C27 | 1.344 (4) |
C10—C11 | 1.441 (4) | C26—H26 | 0.9500 |
C11—C12 | 1.203 (4) | C27—H27 | 0.9500 |
C12—C13 | 1.427 (4) | C28—N3 | 1.141 (3) |
C13—C14 | 1.398 (4) | C28—C29 | 1.438 (4) |
C13—C18 | 1.403 (4) | C29—C30 | 1.438 (4) |
C14—C15 | 1.378 (4) | C30—N4 | 1.154 (4) |
C14—H14 | 0.9500 | C31—N5 | 1.152 (4) |
C15—C16 | 1.384 (5) | C31—C32 | 1.432 (4) |
C15—H15 | 0.9500 | C32—C35 | 1.373 (4) |
C16—C17 | 1.373 (5) | C32—C33 | 1.436 (4) |
C16—H16 | 0.9500 | C33—N6 | 1.143 (3) |
C17—C18 | 1.381 (5) | C34—C36i | 1.338 (4) |
C17—H17 | 0.9500 | C34—C35 | 1.443 (4) |
C18—H18 | 0.9500 | C34—H34 | 0.9500 |
C11'—C12' | 1.195 (4) | C35—C36 | 1.440 (4) |
C12'—C13' | 1.429 (4) | C36—H36 | 0.9500 |
C1A—C1—C2 | 119.0 (3) | C12'—C11'—C10 | 172.8 (3) |
C1A—C1—H1 | 120.5 | C11'—C12'—C13' | 178.8 (4) |
C2—C1—H1 | 120.5 | C14'—C13'—C18' | 119.6 (3) |
C1—C1A—C4A | 119.9 (3) | C14'—C13'—C12' | 120.9 (3) |
C1—C1A—C9 | 132.1 (3) | C18'—C13'—C12' | 119.5 (3) |
C4A—C1A—C9 | 108.0 (3) | C15'—C14'—C13' | 120.0 (4) |
C1—C2—C3 | 121.2 (3) | C15'—C14'—H14' | 120.0 |
C1—C2—H2 | 119.4 | C13'—C14'—H14' | 120.0 |
C3—C2—H2 | 119.4 | C16'—C15'—C14' | 120.4 (4) |
C4—C3—C2 | 119.6 (3) | C16'—C15'—H15' | 119.8 |
C4—C3—H3 | 120.2 | C14'—C15'—H15' | 119.8 |
C2—C3—H3 | 120.2 | C17'—C16'—C15' | 119.3 (4) |
C4A—C4—C3 | 119.6 (3) | C17'—C16'—H16' | 120.3 |
C4A—C4—H4 | 120.2 | C15'—C16'—H16' | 120.3 |
C3—C4—H4 | 120.2 | C16'—C17'—C18' | 121.4 (4) |
C4—C4A—C1A | 120.7 (3) | C16'—C17'—H17' | 119.3 |
C4—C4A—C5A | 130.2 (3) | C18'—C17'—H17' | 119.3 |
C1A—C4A—C5A | 109.1 (3) | C17'—C18'—C13' | 119.3 (4) |
C6—C5—C5A | 118.9 (3) | C17'—C18'—H18' | 120.4 |
C6—C5—H5 | 120.6 | C13'—C18'—H18' | 120.4 |
C5A—C5—H5 | 120.6 | N1—C19—C20 | 178.0 (4) |
C5—C5A—C8A | 120.5 (3) | C22—C20—C19 | 122.8 (3) |
C5—C5A—C4A | 130.9 (3) | C22—C20—C21 | 121.8 (3) |
C8A—C5A—C4A | 108.6 (3) | C19—C20—C21 | 115.3 (3) |
C7—C6—C5 | 120.3 (3) | N2—C21—C20 | 179.2 (3) |
C7—C6—H6 | 119.8 | C20—C22—C23 | 121.9 (3) |
C5—C6—H6 | 119.8 | C20—C22—C27 | 120.6 (3) |
C8—C7—C6 | 121.5 (3) | C23—C22—C27 | 117.4 (3) |
C8—C7—H7 | 119.3 | C24—C23—C22 | 120.9 (3) |
C6—C7—H7 | 119.3 | C24—C23—H23 | 119.6 |
C7—C8—C8A | 119.4 (3) | C22—C23—H23 | 119.6 |
C7—C8—H8 | 120.3 | C23—C24—C25 | 121.9 (3) |
C8A—C8—H8 | 120.3 | C23—C24—H24 | 119.0 |
C8—C8A—C5A | 119.5 (3) | C25—C24—H24 | 119.0 |
C8—C8A—C9 | 133.2 (3) | C29—C25—C26 | 122.2 (3) |
C5A—C8A—C9 | 107.3 (3) | C29—C25—C24 | 120.5 (3) |
C10—C9—C1A | 127.2 (3) | C26—C25—C24 | 117.3 (3) |
C10—C9—C8A | 125.8 (3) | C27—C26—C25 | 120.9 (3) |
C1A—C9—C8A | 106.9 (2) | C27—C26—H26 | 119.6 |
C9—C10—C11' | 123.5 (3) | C25—C26—H26 | 119.6 |
C9—C10—C11 | 124.4 (3) | C26—C27—C22 | 121.6 (3) |
C11'—C10—C11 | 112.0 (3) | C26—C27—H27 | 119.2 |
C12—C11—C10 | 173.3 (3) | C22—C27—H27 | 119.2 |
C11—C12—C13 | 177.1 (3) | N3—C28—C29 | 178.4 (4) |
C14—C13—C18 | 118.9 (3) | C25—C29—C28 | 123.8 (3) |
C14—C13—C12 | 121.0 (3) | C25—C29—C30 | 120.9 (3) |
C18—C13—C12 | 120.1 (3) | C28—C29—C30 | 115.3 (3) |
C15—C14—C13 | 121.2 (3) | N4—C30—C29 | 178.6 (4) |
C15—C14—H14 | 119.4 | N5—C31—C32 | 178.9 (3) |
C13—C14—H14 | 119.4 | C35—C32—C31 | 121.1 (3) |
C14—C15—C16 | 119.0 (4) | C35—C32—C33 | 122.8 (3) |
C14—C15—H15 | 120.5 | C31—C32—C33 | 116.1 (3) |
C16—C15—H15 | 120.5 | N6—C33—C32 | 178.4 (4) |
C17—C16—C15 | 120.9 (4) | C36i—C34—C35 | 121.8 (3) |
C17—C16—H16 | 119.6 | C36i—C34—H34 | 119.1 |
C15—C16—H16 | 119.6 | C35—C34—H34 | 119.1 |
C16—C17—C18 | 120.8 (3) | C32—C35—C36 | 120.9 (3) |
C16—C17—H17 | 119.6 | C32—C35—C34 | 121.8 (3) |
C18—C17—H17 | 119.6 | C36—C35—C34 | 117.3 (3) |
C17—C18—C13 | 119.3 (3) | C34i—C36—C35 | 120.9 (3) |
C17—C18—H18 | 120.3 | C34i—C36—H36 | 119.5 |
C13—C18—H18 | 120.3 | C35—C36—H36 | 119.5 |
C2—C1—C1A—C4A | −1.0 (4) | C13—C14—C15—C16 | 0.1 (5) |
C2—C1—C1A—C9 | 178.8 (3) | C14—C15—C16—C17 | −0.8 (5) |
C1A—C1—C2—C3 | −0.3 (5) | C15—C16—C17—C18 | 0.7 (5) |
C1—C2—C3—C4 | 1.1 (5) | C16—C17—C18—C13 | 0.0 (5) |
C2—C3—C4—C4A | −0.6 (5) | C14—C13—C18—C17 | −0.7 (4) |
C3—C4—C4A—C1A | −0.6 (5) | C18'—C13'—C14'—C15' | 2.0 (5) |
C3—C4—C4A—C5A | 178.8 (3) | C12'—C13'—C14'—C15' | −177.2 (3) |
C1—C1A—C4A—C4 | 1.4 (4) | C13'—C14'—C15'—C16' | −1.9 (6) |
C9—C1A—C4A—C4 | −178.4 (3) | C14'—C15'—C16'—C17' | 0.3 (6) |
C1—C1A—C4A—C5A | −178.1 (3) | C15'—C16'—C17'—C18' | 1.1 (6) |
C9—C1A—C4A—C5A | 2.1 (3) | C16'—C17'—C18'—C13' | −1.0 (6) |
C6—C5—C5A—C8A | 1.1 (4) | C14'—C13'—C18'—C17' | −0.6 (5) |
C6—C5—C5A—C4A | −178.5 (3) | C12'—C13'—C18'—C17' | 178.6 (3) |
C4—C4A—C5A—C5 | −0.1 (5) | C19—C20—C22—C23 | −5.0 (5) |
C1A—C4A—C5A—C5 | 179.4 (3) | C21—C20—C22—C23 | 176.2 (3) |
C4—C4A—C5A—C8A | −179.7 (3) | C19—C20—C22—C27 | 173.9 (3) |
C1A—C4A—C5A—C8A | −0.2 (3) | C21—C20—C22—C27 | −4.9 (4) |
C5A—C5—C6—C7 | −0.5 (4) | C20—C22—C23—C24 | 177.9 (3) |
C5—C6—C7—C8 | −0.3 (5) | C27—C22—C23—C24 | −1.0 (4) |
C6—C7—C8—C8A | 0.5 (5) | C22—C23—C24—C25 | −1.2 (4) |
C7—C8—C8A—C5A | 0.2 (4) | C23—C24—C25—C29 | −176.9 (3) |
C7—C8—C8A—C9 | −179.3 (3) | C23—C24—C25—C26 | 2.7 (4) |
C5—C5A—C8A—C8 | −1.0 (4) | C29—C25—C26—C27 | 177.5 (3) |
C4A—C5A—C8A—C8 | 178.7 (3) | C24—C25—C26—C27 | −2.1 (4) |
C5—C5A—C8A—C9 | 178.6 (3) | C25—C26—C27—C22 | 0.0 (4) |
C4A—C5A—C8A—C9 | −1.7 (3) | C20—C22—C27—C26 | −177.3 (3) |
C1—C1A—C9—C10 | −5.6 (5) | C23—C22—C27—C26 | 1.6 (4) |
C4A—C1A—C9—C10 | 174.2 (3) | C26—C25—C29—C28 | 2.1 (5) |
C1—C1A—C9—C8A | 177.1 (3) | C24—C25—C29—C28 | −178.4 (3) |
C4A—C1A—C9—C8A | −3.1 (3) | C26—C25—C29—C30 | −177.3 (3) |
C8—C8A—C9—C10 | 5.1 (5) | C24—C25—C29—C30 | 2.3 (4) |
C5A—C8A—C9—C10 | −174.4 (3) | C31—C32—C35—C36 | −179.4 (3) |
C8—C8A—C9—C1A | −177.5 (3) | C33—C32—C35—C36 | 0.2 (4) |
C5A—C8A—C9—C1A | 3.0 (3) | C31—C32—C35—C34 | −0.1 (4) |
C1A—C9—C10—C11' | 0.4 (5) | C33—C32—C35—C34 | 179.5 (3) |
C8A—C9—C10—C11' | 177.2 (3) | C36i—C34—C35—C32 | −178.7 (3) |
C1A—C9—C10—C11 | −178.3 (3) | C36i—C34—C35—C36 | 0.7 (5) |
C8A—C9—C10—C11 | −1.5 (5) | C32—C35—C36—C34i | 178.7 (3) |
C18—C13—C14—C15 | 0.6 (5) | C34—C35—C36—C34i | −0.6 (5) |
C12—C13—C14—C15 | −177.4 (3) |
Symmetry code: (i) −x+1, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
C36—H36···N2i | 0.95 | 2.49 | 3.389 (4) | 159 |
C6—H6···N3 | 0.95 | 2.71 | 3.436 (4) | 134 |
C6—H6···N5 | 0.95 | 2.78 | 3.501 (5) | 134 |
C26—H26···N5 | 0.95 | 2.58 | 3.480 (4) | 157 |
C14—H14···N6 | 0.95 | 2.67 | 3.464 (4) | 141 |
C2—H2···N4ii | 0.95 | 2.78 | 3.651 (5) | 152 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y, −z+1. |