Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602873X/wk2016sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680602873X/wk20163sup2.hkl |
CCDC reference: 618338
Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C26H25N2+·PF6− | F(000) = 528 |
Mr = 510.45 | Dx = 1.398 Mg m−3 |
Triclinic, P1 | Melting point: 216 K |
a = 9.568 (5) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.818 (7) Å | Cell parameters from 1175 reflections |
c = 12.523 (7) Å | θ = 2.7–21.0° |
α = 112.956 (8)° | µ = 0.18 mm−1 |
β = 109.260 (8)° | T = 293 K |
γ = 91.257 (8)° | Prism, yellow |
V = 1212.3 (12) Å3 | 0.22 × 0.18 × 0.16 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 4200 independent reflections |
Radiation source: fine-focus sealed tube | 2271 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.962, Tmax = 0.972 | k = −14→11 |
6505 measured reflections | l = −9→14 |
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)] = 0.073 | H-atom parameters constrained |
wR(F2) = 0.236 | w = 1/[σ2(Fo2) + (0.1446P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.98 | (Δ/σ)max < 0.001 |
4200 reflections | Δρmax = 0.42 e Å−3 |
370 parameters | Δρmin = −0.32 e Å−3 |
36 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.006 (4) |
Experimental. 1H NMR (300 MHZ, CDCl3, p.p.m.): δ 0.96 (t, J = 5.4 Hz, 3H, CH3), 1.42 (q, J = 5.4 Hz, 2H, CH2), 2.04 (t, J = 5.4 Hz, 2H, CH2), 4.57 (t, J = 5.4 Hz, 2H, CH2), 6.30 (s, 2H, CH2), 6.87 (d, J = 6.3 Hz, 1H, PhH), 7.10 (t, J = 6.3 Hz, 1H, PhH), 7.38 (t, J = 6.3 hz, 1H, PhH), 7.52 (d, J = 6.3 Hz, 1H, PhH), 7.52 (t, J = 8.4 Hz, 4H, AnH) (An: anthracene), 7.69 (t, J = 8.4 Hz, 4H, AnH), 8.19 (d, J = 8.4 Hz, 2H, AnH), 8.44 (d, J = 8.4 Hz, 2H, AnH), 8.84 (s, 1H, AnH), 11.03 (s, 1H, imiH) (imi: imidazole). |
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 | Occ. (<1) | |
P1 | 0.0152 (4) | 0.8875 (2) | 0.27897 (18) | 0.0611 (9) | 0.677 (4) |
F1 | −0.1043 (5) | 0.7678 (4) | 0.1681 (4) | 0.1087 (15) | 0.677 (4) |
F2 | 0.1146 (6) | 0.7963 (5) | 0.3210 (6) | 0.139 (3) | 0.677 (4) |
F3 | 0.1314 (8) | 1.0029 (4) | 0.3902 (4) | 0.153 (4) | 0.677 (4) |
F4 | −0.0701 (6) | 0.8817 (5) | 0.3665 (5) | 0.1437 (19) | 0.677 (4) |
F5 | −0.0920 (6) | 0.9749 (4) | 0.2415 (5) | 0.135 (2) | 0.677 (4) |
F6 | 0.0940 (7) | 0.8839 (8) | 0.1881 (5) | 0.165 (3) | 0.677 (4) |
P1' | 0.0381 (8) | 0.9013 (6) | 0.2785 (6) | 0.105 (4) | 0.323 (4) |
F1' | −0.1212 (9) | 0.8187 (8) | 0.1846 (9) | 0.1087 (15) | 0.323 (4) |
F3' | 0.1954 (9) | 0.9837 (10) | 0.3732 (9) | 0.127 (5) | 0.323 (4) |
F4' | −0.0417 (13) | 0.9952 (9) | 0.3580 (10) | 0.1437 (19) | 0.323 (4) |
F2' | 0.0489 (12) | 0.8234 (8) | 0.3580 (8) | 0.098 (5) | 0.323 (4) |
F5' | 0.0224 (9) | 0.9788 (7) | 0.1989 (7) | 0.094 (3) | 0.323 (4) |
F6' | 0.1161 (12) | 0.8069 (7) | 0.1992 (9) | 0.104 (4) | 0.323 (4) |
N1 | 0.5511 (3) | −0.0069 (3) | 0.3001 (3) | 0.0629 (9) | |
N2 | 0.7033 (3) | 0.1554 (2) | 0.3367 (3) | 0.0578 (8) | |
C1 | 0.7889 (4) | 0.4618 (3) | 0.4448 (3) | 0.0604 (10) | |
C2 | 0.7342 (5) | 0.4620 (5) | 0.5378 (4) | 0.0814 (12) | |
H2 | 0.7293 | 0.3900 | 0.5509 | 0.098* | |
C3 | 0.6895 (5) | 0.5613 (7) | 0.6066 (5) | 0.1069 (18) | |
H3 | 0.6535 | 0.5570 | 0.6656 | 0.128* | |
C4 | 0.6964 (5) | 0.6724 (6) | 0.5908 (5) | 0.1067 (18) | |
H4 | 0.6679 | 0.7419 | 0.6410 | 0.128* | |
C5 | 0.7448 (5) | 0.6784 (4) | 0.5024 (5) | 0.0875 (14) | |
H5 | 0.7476 | 0.7521 | 0.4920 | 0.105* | |
C6 | 0.7912 (4) | 0.5744 (3) | 0.4254 (4) | 0.0628 (10) | |
C7 | 0.8407 (4) | 0.5776 (4) | 0.3342 (4) | 0.0677 (11) | |
H7 | 0.8427 | 0.6506 | 0.3225 | 0.081* | |
C8 | 0.8873 (4) | 0.4767 (4) | 0.2597 (3) | 0.0628 (10) | |
C9 | 0.9369 (5) | 0.4814 (5) | 0.1660 (4) | 0.0889 (14) | |
H9 | 0.9383 | 0.5546 | 0.1548 | 0.107* | |
C10 | 0.9817 (6) | 0.3842 (7) | 0.0934 (5) | 0.1031 (17) | |
H10 | 1.0122 | 0.3897 | 0.0322 | 0.124* | |
C11 | 0.9819 (5) | 0.2743 (6) | 0.1108 (5) | 0.0983 (16) | |
H11 | 1.0124 | 0.2066 | 0.0601 | 0.118* | |
C12 | 0.9386 (4) | 0.2640 (4) | 0.1999 (4) | 0.0813 (13) | |
H12 | 0.9416 | 0.1898 | 0.2095 | 0.098* | |
C13 | 0.8884 (4) | 0.3640 (3) | 0.2795 (3) | 0.0601 (10) | |
C14 | 0.8390 (4) | 0.3605 (3) | 0.3721 (3) | 0.0584 (10) | |
C15 | 0.8483 (4) | 0.2444 (3) | 0.3968 (4) | 0.0722 (12) | |
H15A | 0.9224 | 0.2013 | 0.3672 | 0.087* | |
H15B | 0.8835 | 0.2697 | 0.4862 | 0.087* | |
C16 | 0.5743 (4) | 0.1405 (3) | 0.2336 (3) | 0.0549 (9) | |
C17 | 0.5305 (4) | 0.2061 (4) | 0.1603 (4) | 0.0703 (11) | |
H17 | 0.5930 | 0.2756 | 0.1737 | 0.084* | |
C18 | 0.3902 (4) | 0.1633 (4) | 0.0669 (4) | 0.0766 (12) | |
H18 | 0.3579 | 0.2051 | 0.0161 | 0.092* | |
C19 | 0.2953 (4) | 0.0597 (4) | 0.0458 (4) | 0.0783 (12) | |
H19 | 0.2017 | 0.0339 | −0.0185 | 0.094* | |
C20 | 0.3370 (4) | −0.0055 (4) | 0.1181 (4) | 0.0724 (11) | |
H20 | 0.2736 | −0.0745 | 0.1048 | 0.087* | |
C21 | 0.4773 (4) | 0.0367 (3) | 0.2114 (3) | 0.0561 (9) | |
C22 | 0.6851 (4) | 0.0664 (3) | 0.3710 (3) | 0.0616 (10) | |
H22 | 0.7562 | 0.0556 | 0.4363 | 0.074* | |
C23 | 0.4932 (5) | −0.1165 (4) | 0.3130 (4) | 0.0802 (13) | |
H23A | 0.3927 | −0.1099 | 0.3140 | 0.096* | |
H23B | 0.5564 | −0.1145 | 0.3925 | 0.096* | |
C24 | 0.4878 (5) | −0.2396 (4) | 0.2109 (5) | 0.0872 (14) | |
H24A | 0.5893 | −0.2512 | 0.2154 | 0.105* | |
H24B | 0.4329 | −0.2393 | 0.1307 | 0.105* | |
C25 | 0.4119 (6) | −0.3479 (4) | 0.2214 (5) | 0.1031 (16) | |
H25A | 0.4649 | −0.3456 | 0.3031 | 0.124* | |
H25B | 0.3097 | −0.3368 | 0.2146 | 0.124* | |
C26 | 0.4084 (7) | −0.4728 (5) | 0.1242 (6) | 0.133 (2) | |
H26A | 0.3589 | −0.5367 | 0.1352 | 0.199* | |
H26B | 0.5094 | −0.4857 | 0.1319 | 0.199* | |
H26C | 0.3547 | −0.4764 | 0.0429 | 0.199* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0774 (17) | 0.0579 (13) | 0.0434 (12) | 0.0118 (11) | 0.0185 (11) | 0.0196 (10) |
F1 | 0.099 (2) | 0.073 (3) | 0.120 (3) | 0.007 (2) | 0.002 (2) | 0.038 (3) |
F2 | 0.111 (4) | 0.138 (4) | 0.171 (7) | 0.057 (4) | 0.032 (4) | 0.082 (4) |
F3 | 0.199 (7) | 0.073 (3) | 0.094 (4) | −0.058 (4) | −0.053 (4) | 0.037 (3) |
F4 | 0.187 (5) | 0.151 (4) | 0.155 (4) | 0.062 (4) | 0.111 (4) | 0.085 (4) |
F5 | 0.152 (5) | 0.109 (3) | 0.145 (4) | 0.067 (3) | 0.030 (4) | 0.072 (3) |
F6 | 0.158 (6) | 0.239 (10) | 0.118 (4) | −0.021 (7) | 0.082 (4) | 0.072 (6) |
P1' | 0.081 (5) | 0.121 (7) | 0.158 (9) | 0.040 (4) | 0.033 (5) | 0.110 (6) |
F1' | 0.099 (2) | 0.073 (3) | 0.120 (3) | 0.007 (2) | 0.002 (2) | 0.038 (3) |
F3' | 0.091 (7) | 0.114 (10) | 0.143 (11) | 0.010 (6) | 0.020 (7) | 0.042 (8) |
F4' | 0.187 (5) | 0.151 (4) | 0.155 (4) | 0.062 (4) | 0.111 (4) | 0.085 (4) |
F2' | 0.134 (11) | 0.084 (7) | 0.072 (5) | −0.028 (7) | −0.006 (6) | 0.066 (5) |
F5' | 0.087 (6) | 0.117 (7) | 0.112 (6) | 0.040 (5) | 0.028 (5) | 0.090 (6) |
F6' | 0.130 (8) | 0.081 (6) | 0.098 (7) | 0.021 (6) | 0.062 (6) | 0.016 (5) |
N1 | 0.0499 (17) | 0.0609 (18) | 0.077 (2) | −0.0045 (15) | 0.0079 (16) | 0.0413 (16) |
N2 | 0.0454 (16) | 0.0509 (16) | 0.0709 (19) | −0.0032 (13) | 0.0044 (14) | 0.0341 (15) |
C1 | 0.0396 (18) | 0.067 (2) | 0.062 (2) | −0.0053 (17) | 0.0023 (17) | 0.0287 (19) |
C2 | 0.059 (2) | 0.098 (3) | 0.078 (3) | −0.007 (2) | 0.012 (2) | 0.039 (3) |
C3 | 0.073 (3) | 0.144 (5) | 0.085 (3) | −0.002 (3) | 0.028 (3) | 0.032 (4) |
C4 | 0.069 (3) | 0.122 (5) | 0.097 (4) | 0.028 (3) | 0.023 (3) | 0.020 (3) |
C5 | 0.061 (3) | 0.073 (3) | 0.102 (4) | 0.009 (2) | 0.004 (3) | 0.032 (3) |
C6 | 0.045 (2) | 0.054 (2) | 0.071 (2) | 0.0023 (16) | −0.0006 (18) | 0.0264 (19) |
C7 | 0.057 (2) | 0.058 (2) | 0.083 (3) | −0.0023 (18) | 0.003 (2) | 0.043 (2) |
C8 | 0.051 (2) | 0.068 (2) | 0.062 (2) | −0.0058 (18) | 0.0032 (18) | 0.035 (2) |
C9 | 0.084 (3) | 0.099 (4) | 0.080 (3) | −0.008 (3) | 0.015 (3) | 0.048 (3) |
C10 | 0.089 (4) | 0.133 (5) | 0.076 (3) | −0.006 (3) | 0.025 (3) | 0.039 (3) |
C11 | 0.077 (3) | 0.108 (4) | 0.075 (3) | 0.004 (3) | 0.018 (3) | 0.012 (3) |
C12 | 0.067 (3) | 0.071 (3) | 0.081 (3) | −0.001 (2) | 0.009 (2) | 0.022 (2) |
C13 | 0.047 (2) | 0.053 (2) | 0.063 (2) | −0.0056 (16) | 0.0043 (18) | 0.0211 (18) |
C14 | 0.0415 (19) | 0.052 (2) | 0.069 (2) | −0.0068 (16) | −0.0007 (17) | 0.0301 (18) |
C15 | 0.047 (2) | 0.067 (2) | 0.094 (3) | −0.0099 (18) | −0.0027 (19) | 0.050 (2) |
C16 | 0.0422 (18) | 0.055 (2) | 0.060 (2) | 0.0021 (16) | 0.0046 (16) | 0.0287 (17) |
C17 | 0.052 (2) | 0.072 (2) | 0.082 (3) | −0.0011 (19) | 0.0036 (19) | 0.045 (2) |
C18 | 0.060 (2) | 0.086 (3) | 0.083 (3) | 0.012 (2) | 0.004 (2) | 0.054 (2) |
C19 | 0.050 (2) | 0.083 (3) | 0.079 (3) | −0.002 (2) | −0.003 (2) | 0.035 (2) |
C20 | 0.051 (2) | 0.072 (2) | 0.082 (3) | −0.0038 (19) | 0.007 (2) | 0.036 (2) |
C21 | 0.0461 (19) | 0.054 (2) | 0.063 (2) | 0.0009 (16) | 0.0108 (17) | 0.0279 (17) |
C22 | 0.052 (2) | 0.064 (2) | 0.068 (2) | 0.0029 (18) | 0.0064 (18) | 0.0400 (19) |
C23 | 0.072 (3) | 0.075 (3) | 0.098 (3) | −0.011 (2) | 0.015 (2) | 0.055 (3) |
C24 | 0.072 (3) | 0.073 (3) | 0.114 (4) | −0.001 (2) | 0.016 (3) | 0.052 (3) |
C25 | 0.089 (3) | 0.079 (3) | 0.139 (4) | −0.008 (3) | 0.018 (3) | 0.065 (3) |
C26 | 0.128 (5) | 0.080 (4) | 0.158 (5) | −0.008 (3) | 0.014 (4) | 0.051 (4) |
P1—F6 | 1.547 (4) | C9—H9 | 0.9300 |
P1—F5 | 1.563 (4) | C10—C11 | 1.398 (7) |
P1—F3 | 1.570 (3) | C10—H10 | 0.9300 |
P1—F2 | 1.582 (4) | C11—C12 | 1.356 (7) |
P1—F4 | 1.588 (4) | C11—H11 | 0.9300 |
P1—F1 | 1.608 (3) | C12—C13 | 1.429 (5) |
P1'—F6' | 1.566 (5) | C12—H12 | 0.9300 |
P1'—F5' | 1.573 (5) | C13—C14 | 1.403 (5) |
P1'—F3' | 1.574 (5) | C14—C15 | 1.518 (5) |
P1'—F4' | 1.575 (5) | C15—H15A | 0.9700 |
P1'—F2' | 1.582 (4) | C15—H15B | 0.9700 |
P1'—F1' | 1.586 (5) | C16—C17 | 1.392 (5) |
N1—C22 | 1.335 (4) | C16—C21 | 1.398 (5) |
N1—C21 | 1.394 (4) | C17—C18 | 1.378 (5) |
N1—C23 | 1.484 (5) | C17—H17 | 0.9300 |
N2—C22 | 1.310 (4) | C18—C19 | 1.391 (6) |
N2—C16 | 1.408 (4) | C18—H18 | 0.9300 |
N2—C15 | 1.493 (4) | C19—C20 | 1.375 (5) |
C1—C14 | 1.398 (5) | C19—H19 | 0.9300 |
C1—C2 | 1.425 (6) | C20—C21 | 1.378 (5) |
C1—C6 | 1.443 (5) | C20—H20 | 0.9300 |
C2—C3 | 1.334 (7) | C22—H22 | 0.9300 |
C2—H2 | 0.9300 | C23—C24 | 1.502 (6) |
C3—C4 | 1.406 (8) | C23—H23A | 0.9700 |
C3—H3 | 0.9300 | C23—H23B | 0.9700 |
C4—C5 | 1.358 (7) | C24—C25 | 1.528 (6) |
C4—H4 | 0.9300 | C24—H24A | 0.9700 |
C5—C6 | 1.422 (6) | C24—H24B | 0.9700 |
C5—H5 | 0.9300 | C25—C26 | 1.494 (7) |
C6—C7 | 1.385 (6) | C25—H25A | 0.9700 |
C7—C8 | 1.387 (5) | C25—H25B | 0.9700 |
C7—H7 | 0.9300 | C26—H26A | 0.9600 |
C8—C9 | 1.421 (6) | C26—H26B | 0.9600 |
C8—C13 | 1.446 (5) | C26—H26C | 0.9600 |
C9—C10 | 1.339 (6) | ||
F6—P1—F5 | 92.9 (4) | C11—C10—H10 | 120.4 |
F6—P1—F3 | 93.0 (3) | C12—C11—C10 | 121.6 (5) |
F5—P1—F3 | 91.2 (3) | C12—C11—H11 | 119.2 |
F6—P1—F2 | 91.4 (4) | C10—C11—H11 | 119.2 |
F5—P1—F2 | 175.5 (4) | C11—C12—C13 | 121.8 (5) |
F3—P1—F2 | 90.1 (3) | C11—C12—H12 | 119.1 |
F6—P1—F4 | 176.2 (4) | C13—C12—H12 | 119.1 |
F5—P1—F4 | 88.6 (3) | C14—C13—C12 | 125.6 (4) |
F3—P1—F4 | 90.5 (3) | C14—C13—C8 | 118.4 (3) |
F2—P1—F4 | 87.0 (3) | C12—C13—C8 | 116.0 (4) |
F6—P1—F1 | 88.5 (3) | C1—C14—C13 | 122.1 (3) |
F5—P1—F1 | 89.8 (3) | C1—C14—C15 | 119.8 (4) |
F3—P1—F1 | 178.2 (3) | C13—C14—C15 | 118.0 (3) |
F2—P1—F1 | 88.8 (3) | N2—C15—C14 | 114.4 (3) |
F4—P1—F1 | 88.0 (3) | N2—C15—H15A | 108.7 |
F6'—P1'—F5' | 91.1 (4) | C14—C15—H15A | 108.7 |
F6'—P1'—F3' | 90.6 (5) | N2—C15—H15B | 108.7 |
F5'—P1'—F3' | 90.8 (5) | C14—C15—H15B | 108.7 |
F6'—P1'—F4' | 179.4 (5) | H15A—C15—H15B | 107.6 |
F5'—P1'—F4' | 89.3 (4) | C17—C16—C21 | 120.1 (3) |
F3'—P1'—F4' | 89.9 (4) | C17—C16—N2 | 134.0 (3) |
F6'—P1'—F2' | 90.0 (4) | C21—C16—N2 | 105.9 (3) |
F5'—P1'—F2' | 178.4 (5) | C18—C17—C16 | 116.9 (3) |
F3'—P1'—F2' | 90.4 (4) | C18—C17—H17 | 121.6 |
F4'—P1'—F2' | 89.7 (4) | C16—C17—H17 | 121.6 |
F6'—P1'—F1' | 90.0 (4) | C17—C18—C19 | 122.2 (4) |
F5'—P1'—F1' | 89.7 (4) | C17—C18—H18 | 118.9 |
F3'—P1'—F1' | 179.2 (5) | C19—C18—H18 | 118.9 |
F4'—P1'—F1' | 89.5 (5) | C20—C19—C18 | 121.4 (4) |
F2'—P1'—F1' | 89.1 (4) | C20—C19—H19 | 119.3 |
C22—N1—C21 | 107.9 (3) | C18—C19—H19 | 119.3 |
C22—N1—C23 | 125.6 (3) | C19—C20—C21 | 116.5 (4) |
C21—N1—C23 | 126.5 (3) | C19—C20—H20 | 121.7 |
C22—N2—C16 | 108.4 (3) | C21—C20—H20 | 121.7 |
C22—N2—C15 | 121.1 (3) | C20—C21—N1 | 130.6 (3) |
C16—N2—C15 | 130.2 (3) | C20—C21—C16 | 122.8 (3) |
C14—C1—C2 | 124.4 (4) | N1—C21—C16 | 106.6 (3) |
C14—C1—C6 | 118.7 (4) | N2—C22—N1 | 111.1 (3) |
C2—C1—C6 | 116.9 (4) | N2—C22—H22 | 124.4 |
C3—C2—C1 | 122.6 (5) | N1—C22—H22 | 124.4 |
C3—C2—H2 | 118.7 | N1—C23—C24 | 113.9 (4) |
C1—C2—H2 | 118.7 | N1—C23—H23A | 108.8 |
C2—C3—C4 | 120.6 (5) | C24—C23—H23A | 108.8 |
C2—C3—H3 | 119.7 | N1—C23—H23B | 108.8 |
C4—C3—H3 | 119.7 | C24—C23—H23B | 108.8 |
C5—C4—C3 | 120.1 (5) | H23A—C23—H23B | 107.7 |
C5—C4—H4 | 120.0 | C23—C24—C25 | 111.5 (4) |
C3—C4—H4 | 120.0 | C23—C24—H24A | 109.3 |
C4—C5—C6 | 121.3 (5) | C25—C24—H24A | 109.3 |
C4—C5—H5 | 119.4 | C23—C24—H24B | 109.3 |
C6—C5—H5 | 119.4 | C25—C24—H24B | 109.3 |
C7—C6—C5 | 122.6 (4) | H24A—C24—H24B | 108.0 |
C7—C6—C1 | 119.0 (3) | C26—C25—C24 | 113.4 (5) |
C5—C6—C1 | 118.5 (4) | C26—C25—H25A | 108.9 |
C6—C7—C8 | 122.8 (4) | C24—C25—H25A | 108.9 |
C6—C7—H7 | 118.6 | C26—C25—H25B | 108.9 |
C8—C7—H7 | 118.6 | C24—C25—H25B | 108.9 |
C7—C8—C9 | 122.0 (4) | H25A—C25—H25B | 107.7 |
C7—C8—C13 | 119.0 (4) | C25—C26—H26A | 109.5 |
C9—C8—C13 | 118.9 (4) | C25—C26—H26B | 109.5 |
C10—C9—C8 | 122.4 (5) | H26A—C26—H26B | 109.5 |
C10—C9—H9 | 118.8 | C25—C26—H26C | 109.5 |
C8—C9—H9 | 118.8 | H26A—C26—H26C | 109.5 |
C9—C10—C11 | 119.2 (5) | H26B—C26—H26C | 109.5 |
C9—C10—H10 | 120.4 | ||
C14—C1—C2—C3 | 178.9 (4) | C8—C13—C14—C15 | −176.9 (3) |
C6—C1—C2—C3 | −1.4 (6) | C22—N2—C15—C14 | −164.7 (3) |
C1—C2—C3—C4 | −0.7 (7) | C16—N2—C15—C14 | 21.9 (6) |
C2—C3—C4—C5 | 1.9 (8) | C1—C14—C15—N2 | 83.1 (4) |
C3—C4—C5—C6 | −0.9 (7) | C13—C14—C15—N2 | −99.8 (4) |
C4—C5—C6—C7 | 179.8 (4) | C22—N2—C16—C17 | 179.4 (4) |
C4—C5—C6—C1 | −1.3 (6) | C15—N2—C16—C17 | −6.6 (7) |
C14—C1—C6—C7 | 1.0 (5) | C22—N2—C16—C21 | 1.1 (4) |
C2—C1—C6—C7 | −178.7 (3) | C15—N2—C16—C21 | 175.1 (3) |
C14—C1—C6—C5 | −178.0 (3) | C21—C16—C17—C18 | −0.3 (6) |
C2—C1—C6—C5 | 2.4 (5) | N2—C16—C17—C18 | −178.4 (4) |
C5—C6—C7—C8 | 179.4 (3) | C16—C17—C18—C19 | 0.2 (6) |
C1—C6—C7—C8 | 0.5 (5) | C17—C18—C19—C20 | 0.2 (7) |
C6—C7—C8—C9 | 179.6 (3) | C18—C19—C20—C21 | −0.4 (6) |
C6—C7—C8—C13 | −1.7 (5) | C19—C20—C21—N1 | 179.2 (4) |
C7—C8—C9—C10 | −179.8 (4) | C19—C20—C21—C16 | 0.3 (6) |
C13—C8—C9—C10 | 1.5 (6) | C22—N1—C21—C20 | −179.4 (4) |
C8—C9—C10—C11 | −0.9 (7) | C23—N1—C21—C20 | 1.6 (6) |
C9—C10—C11—C12 | −0.4 (7) | C22—N1—C21—C16 | −0.3 (4) |
C10—C11—C12—C13 | 0.9 (7) | C23—N1—C21—C16 | −179.4 (3) |
C11—C12—C13—C14 | 178.7 (4) | C17—C16—C21—C20 | 0.1 (6) |
C11—C12—C13—C8 | −0.3 (5) | N2—C16—C21—C20 | 178.7 (3) |
C7—C8—C13—C14 | 1.3 (5) | C17—C16—C21—N1 | −179.0 (3) |
C9—C8—C13—C14 | −179.9 (3) | N2—C16—C21—N1 | −0.5 (4) |
C7—C8—C13—C12 | −179.6 (3) | C16—N2—C22—N1 | −1.3 (4) |
C9—C8—C13—C12 | −0.9 (5) | C15—N2—C22—N1 | −176.0 (3) |
C2—C1—C14—C13 | 178.4 (3) | C21—N1—C22—N2 | 1.0 (4) |
C6—C1—C14—C13 | −1.3 (5) | C23—N1—C22—N2 | −179.9 (3) |
C2—C1—C14—C15 | −4.7 (5) | C22—N1—C23—C24 | −107.8 (4) |
C6—C1—C14—C15 | 175.7 (3) | C21—N1—C23—C24 | 71.1 (5) |
C12—C13—C14—C1 | −178.8 (3) | N1—C23—C24—C25 | −173.9 (4) |
C8—C13—C14—C1 | 0.1 (5) | C23—C24—C25—C26 | −178.1 (4) |
C12—C13—C14—C15 | 4.2 (5) |