Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804034026/wk6030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804034026/wk60302sup2.hkl |
CCDC reference: 229990
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
C33H29N | F(000) = 468 |
Mr = 439.57 | Dx = 1.193 Mg m−3 |
Triclinic, P1 | Melting point: 282 K |
a = 9.891 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.188 (4) Å | Cell parameters from 689 reflections |
c = 13.592 (5) Å | θ = 2.3–22.3° |
α = 106.179 (7)° | µ = 0.07 mm−1 |
β = 106.822 (7)° | T = 293 K |
γ = 97.750 (7)° | Block, yellow |
V = 1224.1 (7) Å3 | 0.32 × 0.24 × 0.20 mm |
Z = 2 |
Bruker SMART1000 CCD area-detector diffractometer | 4975 independent reflections |
Radiation source: fine-focus sealed tube | 2036 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scans | θmax = 26.5°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→12 |
Tmin = 0.881, Tmax = 0.990 | k = −12→9 |
7130 measured reflections | l = −15→17 |
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)] = 0.077 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.208 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0803P)2] where P = (Fo2 + 2Fc2)/3 |
4975 reflections | (Δ/σ)max < 0.001 |
305 parameters | Δρmax = 0.23 e Å−3 |
3 restraints | Δρmin = −0.23 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. Disorder prsent in n-Pr group, modelled over 2 sites with isotropic adps, distance restraints and occupancies 0.621 (14) and 0.379 (14). |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1 | 0.6097 (3) | 0.1547 (2) | 0.33354 (18) | 0.0464 (7) | |
C1 | 0.7259 (4) | 0.2229 (3) | 0.1282 (2) | 0.0462 (8) | |
C2 | 0.8757 (4) | 0.2315 (4) | 0.1809 (3) | 0.0620 (10) | |
H2A | 0.9012 | 0.1907 | 0.2349 | 0.074* | |
C3 | 0.9818 (4) | 0.2969 (4) | 0.1549 (3) | 0.0776 (12) | |
H3A | 1.0783 | 0.2991 | 0.1903 | 0.093* | |
C4 | 0.9482 (5) | 0.3612 (5) | 0.0755 (3) | 0.0861 (14) | |
H4A | 1.0219 | 0.4063 | 0.0583 | 0.103* | |
C5 | 0.8094 (5) | 0.3576 (4) | 0.0242 (3) | 0.0745 (12) | |
H5A | 0.7884 | 0.4015 | −0.0281 | 0.089* | |
C6 | 0.6936 (4) | 0.2893 (3) | 0.0470 (2) | 0.0532 (9) | |
C7 | 0.5511 (4) | 0.2856 (3) | −0.0067 (3) | 0.0589 (10) | |
H7A | 0.5310 | 0.3300 | −0.0587 | 0.071* | |
C8 | 0.4370 (4) | 0.2182 (3) | 0.0140 (2) | 0.0515 (9) | |
C9 | 0.2915 (4) | 0.2146 (4) | −0.0421 (3) | 0.0714 (11) | |
H9A | 0.2714 | 0.2584 | −0.0945 | 0.086* | |
C10 | 0.1821 (4) | 0.1492 (5) | −0.0213 (3) | 0.0813 (13) | |
H10A | 0.0867 | 0.1472 | −0.0593 | 0.098* | |
C11 | 0.2112 (4) | 0.0834 (4) | 0.0581 (3) | 0.0759 (12) | |
H11A | 0.1345 | 0.0388 | 0.0727 | 0.091* | |
C12 | 0.3484 (4) | 0.0840 (4) | 0.1135 (3) | 0.0575 (9) | |
H12A | 0.3650 | 0.0386 | 0.1650 | 0.069* | |
C13 | 0.4675 (3) | 0.1524 (3) | 0.0945 (2) | 0.0442 (8) | |
C14 | 0.6120 (3) | 0.1543 (3) | 0.1515 (2) | 0.0431 (8) | |
C15 | 0.6398 (4) | 0.0822 (3) | 0.2356 (2) | 0.0486 (9) | |
H15A | 0.5796 | −0.0128 | 0.2033 | 0.058* | |
H15B | 0.7405 | 0.0760 | 0.2565 | 0.058* | |
C19 | 0.6103 (4) | 0.0668 (3) | 0.4028 (2) | 0.0530 (9) | |
H19A | 0.6000 | 0.1214 | 0.4701 | 0.064* | |
H19B | 0.7036 | 0.0422 | 0.4216 | 0.064* | |
C20 | 0.4920 (4) | −0.0663 (3) | 0.3508 (2) | 0.0473 (8) | |
C21 | 0.3473 (4) | −0.0585 (4) | 0.3389 (2) | 0.0542 (9) | |
C22 | 0.3068 (5) | 0.0703 (4) | 0.3711 (3) | 0.0691 (11) | |
H22A | 0.3772 | 0.1542 | 0.3989 | 0.083* | |
C23 | 0.1669 (5) | 0.0744 (5) | 0.3625 (3) | 0.0877 (13) | |
H23A | 0.1433 | 0.1603 | 0.3858 | 0.105* | |
C24 | 0.0596 (6) | −0.0490 (7) | 0.3191 (4) | 0.1057 (17) | |
H24A | −0.0358 | −0.0450 | 0.3128 | 0.127* | |
C25 | 0.0913 (5) | −0.1734 (6) | 0.2863 (4) | 0.0925 (15) | |
H25A | 0.0174 | −0.2548 | 0.2569 | 0.111* | |
C26 | 0.2338 (4) | −0.1839 (4) | 0.2952 (3) | 0.0629 (10) | |
C27 | 0.2708 (5) | −0.3111 (4) | 0.2641 (3) | 0.0733 (12) | |
H27A | 0.1972 | −0.3927 | 0.2355 | 0.088* | |
C28 | 0.4087 (5) | −0.3241 (4) | 0.2729 (3) | 0.0619 (10) | |
C29 | 0.4431 (6) | −0.4569 (4) | 0.2391 (3) | 0.0849 (14) | |
H29A | 0.3694 | −0.5384 | 0.2105 | 0.102* | |
C30 | 0.5777 (7) | −0.4669 (5) | 0.2475 (4) | 0.0964 (16) | |
H30A | 0.5970 | −0.5548 | 0.2236 | 0.116* | |
C31 | 0.6909 (6) | −0.3464 (6) | 0.2920 (3) | 0.0895 (14) | |
H31A | 0.7853 | −0.3547 | 0.2984 | 0.107* | |
C32 | 0.6641 (5) | −0.2172 (4) | 0.3258 (3) | 0.0724 (11) | |
H32A | 0.7412 | −0.1385 | 0.3553 | 0.087* | |
C33 | 0.5234 (4) | −0.1984 (4) | 0.3179 (2) | 0.0539 (9) | |
C16 | 0.7425 (12) | 0.2746 (10) | 0.3940 (8) | 0.060 (4)* | 0.379 (14) |
H16A | 0.8247 | 0.2398 | 0.4268 | 0.072* | 0.379 (14) |
H16B | 0.7661 | 0.3172 | 0.3437 | 0.072* | 0.379 (14) |
C17 | 0.7123 (17) | 0.3819 (9) | 0.4811 (8) | 0.070 (4)* | 0.379 (14) |
H17A | 0.6920 | 0.3395 | 0.5325 | 0.085* | 0.379 (14) |
H17B | 0.6271 | 0.4128 | 0.4482 | 0.085* | 0.379 (14) |
C18 | 0.8415 (19) | 0.5082 (12) | 0.5414 (10) | 0.104 (5)* | 0.379 (14) |
H18A | 0.8177 | 0.5776 | 0.5937 | 0.155* | 0.379 (14) |
H18B | 0.8641 | 0.5478 | 0.4901 | 0.155* | 0.379 (14) |
H18C | 0.9240 | 0.4788 | 0.5785 | 0.155* | 0.379 (14) |
C17' | 0.6394 (10) | 0.3885 (6) | 0.4702 (5) | 0.064 (2)* | 0.621 (14) |
H17C | 0.6126 | 0.3420 | 0.5175 | 0.077* | 0.621 (14) |
H17D | 0.5523 | 0.4066 | 0.4260 | 0.077* | 0.621 (14) |
C18' | 0.7495 (11) | 0.5270 (7) | 0.5392 (5) | 0.088 (3)* | 0.621 (14) |
H18D | 0.7073 | 0.5867 | 0.5839 | 0.132* | 0.621 (14) |
H18E | 0.7766 | 0.5725 | 0.4924 | 0.132* | 0.621 (14) |
H18F | 0.8341 | 0.5093 | 0.5850 | 0.132* | 0.621 (14) |
C16' | 0.7009 (8) | 0.2946 (5) | 0.3976 (4) | 0.0445 (19)* | 0.621 (14) |
H16C | 0.7215 | 0.3403 | 0.3481 | 0.053* | 0.621 (14) |
H16D | 0.7927 | 0.2852 | 0.4425 | 0.053* | 0.621 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0668 (19) | 0.0358 (15) | 0.0322 (13) | 0.0034 (13) | 0.0131 (13) | 0.0128 (12) |
C1 | 0.055 (2) | 0.0404 (19) | 0.0383 (17) | 0.0050 (16) | 0.0173 (16) | 0.0076 (15) |
C2 | 0.056 (2) | 0.074 (3) | 0.055 (2) | 0.007 (2) | 0.0191 (19) | 0.022 (2) |
C3 | 0.053 (3) | 0.102 (3) | 0.068 (3) | 0.000 (2) | 0.018 (2) | 0.024 (2) |
C4 | 0.076 (3) | 0.112 (4) | 0.065 (3) | −0.016 (3) | 0.027 (2) | 0.035 (3) |
C5 | 0.080 (3) | 0.087 (3) | 0.052 (2) | −0.008 (2) | 0.021 (2) | 0.031 (2) |
C6 | 0.063 (2) | 0.055 (2) | 0.0409 (18) | 0.0008 (18) | 0.0209 (17) | 0.0190 (17) |
C7 | 0.075 (3) | 0.064 (2) | 0.0423 (19) | 0.013 (2) | 0.0195 (19) | 0.0257 (18) |
C8 | 0.057 (2) | 0.057 (2) | 0.0379 (18) | 0.0114 (18) | 0.0136 (17) | 0.0159 (17) |
C9 | 0.071 (3) | 0.096 (3) | 0.051 (2) | 0.025 (2) | 0.015 (2) | 0.034 (2) |
C10 | 0.051 (3) | 0.124 (4) | 0.068 (3) | 0.021 (2) | 0.014 (2) | 0.037 (3) |
C11 | 0.054 (3) | 0.108 (3) | 0.061 (2) | 0.005 (2) | 0.018 (2) | 0.030 (2) |
C12 | 0.056 (2) | 0.068 (2) | 0.0454 (19) | 0.0042 (19) | 0.0150 (17) | 0.0212 (18) |
C13 | 0.050 (2) | 0.0437 (19) | 0.0340 (17) | 0.0057 (16) | 0.0130 (15) | 0.0098 (15) |
C14 | 0.055 (2) | 0.0368 (18) | 0.0350 (16) | 0.0044 (16) | 0.0170 (16) | 0.0093 (14) |
C15 | 0.061 (2) | 0.0408 (19) | 0.0451 (18) | 0.0092 (16) | 0.0191 (16) | 0.0161 (16) |
C19 | 0.066 (2) | 0.048 (2) | 0.0442 (18) | 0.0073 (17) | 0.0142 (16) | 0.0226 (17) |
C20 | 0.065 (2) | 0.041 (2) | 0.0373 (17) | 0.0058 (17) | 0.0175 (16) | 0.0178 (16) |
C21 | 0.068 (3) | 0.061 (2) | 0.0409 (18) | 0.014 (2) | 0.0186 (18) | 0.0278 (18) |
C22 | 0.080 (3) | 0.073 (3) | 0.061 (2) | 0.018 (2) | 0.025 (2) | 0.032 (2) |
C23 | 0.080 (3) | 0.111 (4) | 0.090 (3) | 0.040 (3) | 0.034 (3) | 0.047 (3) |
C24 | 0.073 (4) | 0.143 (5) | 0.118 (4) | 0.032 (4) | 0.032 (3) | 0.067 (4) |
C25 | 0.064 (3) | 0.117 (4) | 0.092 (3) | 0.003 (3) | 0.015 (3) | 0.049 (3) |
C26 | 0.062 (3) | 0.075 (3) | 0.047 (2) | −0.001 (2) | 0.0112 (19) | 0.029 (2) |
C27 | 0.088 (3) | 0.066 (3) | 0.049 (2) | −0.014 (2) | 0.011 (2) | 0.023 (2) |
C28 | 0.098 (3) | 0.047 (2) | 0.0401 (19) | 0.006 (2) | 0.024 (2) | 0.0186 (18) |
C29 | 0.143 (5) | 0.050 (3) | 0.056 (2) | 0.010 (3) | 0.031 (3) | 0.018 (2) |
C30 | 0.159 (5) | 0.076 (4) | 0.074 (3) | 0.051 (4) | 0.050 (4) | 0.035 (3) |
C31 | 0.111 (4) | 0.105 (4) | 0.084 (3) | 0.050 (3) | 0.050 (3) | 0.051 (3) |
C32 | 0.104 (4) | 0.063 (3) | 0.075 (3) | 0.033 (2) | 0.044 (2) | 0.039 (2) |
C33 | 0.078 (3) | 0.051 (2) | 0.0399 (18) | 0.012 (2) | 0.0233 (18) | 0.0246 (17) |
N1—C16' | 1.453 (5) | C22—C23 | 1.362 (5) |
N1—C15 | 1.465 (4) | C22—H22A | 0.9300 |
N1—C19 | 1.469 (3) | C23—C24 | 1.385 (6) |
N1—C16 | 1.508 (7) | C23—H23A | 0.9300 |
C1—C14 | 1.405 (4) | C24—C25 | 1.333 (6) |
C1—C2 | 1.426 (4) | C24—H24A | 0.9300 |
C1—C6 | 1.431 (4) | C25—C26 | 1.400 (5) |
C2—C3 | 1.352 (5) | C25—H25A | 0.9300 |
C2—H2A | 0.9300 | C26—C27 | 1.380 (5) |
C3—C4 | 1.397 (5) | C27—C28 | 1.363 (5) |
C3—H3A | 0.9300 | C27—H27A | 0.9300 |
C4—C5 | 1.338 (5) | C28—C29 | 1.423 (5) |
C4—H4A | 0.9300 | C28—C33 | 1.440 (5) |
C5—C6 | 1.416 (5) | C29—C30 | 1.323 (6) |
C5—H5A | 0.9300 | C29—H29A | 0.9300 |
C6—C7 | 1.377 (4) | C30—C31 | 1.397 (6) |
C7—C8 | 1.381 (5) | C30—H30A | 0.9300 |
C7—H7A | 0.9300 | C31—C32 | 1.357 (5) |
C8—C9 | 1.411 (5) | C31—H31A | 0.9300 |
C8—C13 | 1.417 (4) | C32—C33 | 1.408 (5) |
C9—C10 | 1.335 (5) | C32—H32A | 0.9300 |
C9—H9A | 0.9300 | C16—C17 | 1.503 (9) |
C10—C11 | 1.404 (5) | C16—H16A | 0.9700 |
C10—H10A | 0.9300 | C16—H16B | 0.9700 |
C11—C12 | 1.347 (4) | C17—C18 | 1.524 (9) |
C11—H11A | 0.9300 | C17—H17A | 0.9700 |
C12—C13 | 1.413 (4) | C17—H17B | 0.9700 |
C12—H12A | 0.9300 | C18—H18A | 0.9600 |
C13—C14 | 1.409 (4) | C18—H18B | 0.9600 |
C14—C15 | 1.504 (4) | C18—H18C | 0.9600 |
C15—H15A | 0.9700 | C17'—C16' | 1.496 (7) |
C15—H15B | 0.9700 | C17'—C18' | 1.521 (7) |
C19—C20 | 1.505 (4) | C17'—H17C | 0.9700 |
C19—H19A | 0.9700 | C17'—H17D | 0.9700 |
C19—H19B | 0.9700 | C18'—H18D | 0.9600 |
C20—C33 | 1.402 (4) | C18'—H18E | 0.9600 |
C20—C21 | 1.409 (5) | C18'—H18F | 0.9600 |
C21—C22 | 1.414 (5) | C16'—H16C | 0.9700 |
C21—C26 | 1.431 (5) | C16'—H16D | 0.9700 |
C16'—N1—C15 | 115.9 (4) | C22—C23—C24 | 120.3 (5) |
C16'—N1—C19 | 110.5 (3) | C22—C23—H23A | 119.9 |
C15—N1—C19 | 111.0 (2) | C24—C23—H23A | 119.9 |
C16'—N1—C16 | 19.0 (5) | C25—C24—C23 | 120.8 (5) |
C15—N1—C16 | 102.2 (5) | C25—C24—H24A | 119.6 |
C19—N1—C16 | 106.5 (5) | C23—C24—H24A | 119.6 |
C14—C1—C2 | 124.1 (3) | C24—C25—C26 | 121.3 (5) |
C14—C1—C6 | 119.6 (3) | C24—C25—H25A | 119.4 |
C2—C1—C6 | 116.3 (3) | C26—C25—H25A | 119.4 |
C3—C2—C1 | 122.1 (4) | C27—C26—C25 | 122.7 (4) |
C3—C2—H2A | 118.9 | C27—C26—C21 | 117.8 (4) |
C1—C2—H2A | 118.9 | C25—C26—C21 | 119.4 (4) |
C2—C3—C4 | 120.7 (4) | C28—C27—C26 | 123.9 (4) |
C2—C3—H3A | 119.6 | C28—C27—H27A | 118.1 |
C4—C3—H3A | 119.6 | C26—C27—H27A | 118.1 |
C5—C4—C3 | 119.7 (4) | C27—C28—C29 | 122.5 (4) |
C5—C4—H4A | 120.2 | C27—C28—C33 | 118.5 (4) |
C3—C4—H4A | 120.2 | C29—C28—C33 | 119.1 (4) |
C4—C5—C6 | 122.1 (4) | C30—C29—C28 | 121.4 (5) |
C4—C5—H5A | 118.9 | C30—C29—H29A | 119.3 |
C6—C5—H5A | 118.9 | C28—C29—H29A | 119.3 |
C7—C6—C5 | 121.6 (3) | C29—C30—C31 | 120.5 (5) |
C7—C6—C1 | 119.3 (3) | C29—C30—H30A | 119.7 |
C5—C6—C1 | 119.0 (3) | C31—C30—H30A | 119.7 |
C6—C7—C8 | 122.2 (3) | C32—C31—C30 | 120.4 (5) |
C6—C7—H7A | 118.9 | C32—C31—H31A | 119.8 |
C8—C7—H7A | 118.9 | C30—C31—H31A | 119.8 |
C7—C8—C9 | 121.6 (3) | C31—C32—C33 | 122.2 (4) |
C7—C8—C13 | 119.0 (3) | C31—C32—H32A | 118.9 |
C9—C8—C13 | 119.4 (3) | C33—C32—H32A | 118.9 |
C10—C9—C8 | 121.0 (4) | C20—C33—C32 | 123.5 (3) |
C10—C9—H9A | 119.5 | C20—C33—C28 | 120.1 (4) |
C8—C9—H9A | 119.5 | C32—C33—C28 | 116.4 (4) |
C9—C10—C11 | 120.0 (4) | C17—C16—N1 | 109.0 (7) |
C9—C10—H10A | 120.0 | C17—C16—H16A | 109.9 |
C11—C10—H10A | 120.0 | N1—C16—H16A | 109.9 |
C12—C11—C10 | 121.0 (4) | C17—C16—H16B | 109.9 |
C12—C11—H11A | 119.5 | N1—C16—H16B | 109.9 |
C10—C11—H11A | 119.5 | H16A—C16—H16B | 108.3 |
C11—C12—C13 | 121.0 (3) | C16—C17—C18 | 110.9 (9) |
C11—C12—H12A | 119.5 | C16—C17—H17A | 109.5 |
C13—C12—H12A | 119.5 | C18—C17—H17A | 109.5 |
C14—C13—C12 | 122.0 (3) | C16—C17—H17B | 109.5 |
C14—C13—C8 | 120.5 (3) | C18—C17—H17B | 109.5 |
C12—C13—C8 | 117.6 (3) | H17A—C17—H17B | 108.0 |
C1—C14—C13 | 119.4 (3) | C17—C18—H18A | 109.5 |
C1—C14—C15 | 121.8 (3) | C17—C18—H18B | 109.5 |
C13—C14—C15 | 118.9 (3) | H18A—C18—H18B | 109.5 |
N1—C15—C14 | 113.3 (2) | C17—C18—H18C | 109.5 |
N1—C15—H15A | 108.9 | H18A—C18—H18C | 109.5 |
C14—C15—H15A | 108.9 | H18B—C18—H18C | 109.5 |
N1—C15—H15B | 108.9 | C16'—C17'—C18' | 110.7 (6) |
C14—C15—H15B | 108.9 | C16'—C17'—H17C | 109.5 |
H15A—C15—H15B | 107.7 | C18'—C17'—H17C | 109.5 |
N1—C19—C20 | 114.0 (2) | C16'—C17'—H17D | 109.5 |
N1—C19—H19A | 108.7 | C18'—C17'—H17D | 109.5 |
C20—C19—H19A | 108.7 | H17C—C17'—H17D | 108.1 |
N1—C19—H19B | 108.7 | C17'—C18'—H18D | 109.5 |
C20—C19—H19B | 108.7 | C17'—C18'—H18E | 109.5 |
H19A—C19—H19B | 107.6 | H18D—C18'—H18E | 109.5 |
C33—C20—C21 | 119.2 (3) | C17'—C18'—H18F | 109.5 |
C33—C20—C19 | 121.4 (3) | H18D—C18'—H18F | 109.5 |
C21—C20—C19 | 119.3 (3) | H18E—C18'—H18F | 109.5 |
C20—C21—C22 | 122.7 (3) | N1—C16'—C17' | 115.8 (5) |
C20—C21—C26 | 120.5 (4) | N1—C16'—H16C | 108.3 |
C22—C21—C26 | 116.7 (4) | C17'—C16'—H16C | 108.3 |
C23—C22—C21 | 121.4 (4) | N1—C16'—H16D | 108.3 |
C23—C22—H22A | 119.3 | C17'—C16'—H16D | 108.3 |
C21—C22—H22A | 119.3 | H16C—C16'—H16D | 107.4 |
C14—C1—C2—C3 | 179.1 (3) | N1—C19—C20—C21 | −72.8 (4) |
C6—C1—C2—C3 | −0.8 (5) | C33—C20—C21—C22 | 179.3 (3) |
C1—C2—C3—C4 | 1.0 (6) | C19—C20—C21—C22 | 1.9 (4) |
C2—C3—C4—C5 | −0.3 (6) | C33—C20—C21—C26 | 0.9 (4) |
C3—C4—C5—C6 | −0.5 (6) | C19—C20—C21—C26 | −176.6 (3) |
C4—C5—C6—C7 | −179.6 (4) | C20—C21—C22—C23 | −177.5 (3) |
C4—C5—C6—C1 | 0.6 (6) | C26—C21—C22—C23 | 1.0 (5) |
C14—C1—C6—C7 | 0.4 (4) | C21—C22—C23—C24 | −1.5 (6) |
C2—C1—C6—C7 | −179.7 (3) | C22—C23—C24—C25 | 0.7 (7) |
C14—C1—C6—C5 | −179.8 (3) | C23—C24—C25—C26 | 0.4 (7) |
C2—C1—C6—C5 | 0.1 (4) | C24—C25—C26—C27 | 178.6 (4) |
C5—C6—C7—C8 | 179.4 (3) | C24—C25—C26—C21 | −0.9 (6) |
C1—C6—C7—C8 | −0.8 (5) | C20—C21—C26—C27 | −0.8 (5) |
C6—C7—C8—C9 | −179.6 (3) | C22—C21—C26—C27 | −179.4 (3) |
C6—C7—C8—C13 | 1.0 (5) | C20—C21—C26—C25 | 178.7 (3) |
C7—C8—C9—C10 | −180.0 (4) | C22—C21—C26—C25 | 0.1 (5) |
C13—C8—C9—C10 | −0.5 (5) | C25—C26—C27—C28 | −179.3 (4) |
C8—C9—C10—C11 | 0.4 (6) | C21—C26—C27—C28 | 0.1 (5) |
C9—C10—C11—C12 | −0.6 (6) | C26—C27—C28—C29 | −179.4 (3) |
C10—C11—C12—C13 | 0.9 (6) | C26—C27—C28—C33 | 0.5 (5) |
C11—C12—C13—C14 | 180.0 (3) | C27—C28—C29—C30 | 179.4 (4) |
C11—C12—C13—C8 | −0.9 (5) | C33—C28—C29—C30 | −0.5 (6) |
C7—C8—C13—C14 | −0.7 (5) | C28—C29—C30—C31 | 1.2 (7) |
C9—C8—C13—C14 | 179.9 (3) | C29—C30—C31—C32 | −0.9 (7) |
C7—C8—C13—C12 | −179.8 (3) | C30—C31—C32—C33 | −0.1 (6) |
C9—C8—C13—C12 | 0.8 (5) | C21—C20—C33—C32 | 179.7 (3) |
C2—C1—C14—C13 | 179.9 (3) | C19—C20—C33—C32 | −2.9 (4) |
C6—C1—C14—C13 | −0.2 (4) | C21—C20—C33—C28 | −0.2 (4) |
C2—C1—C14—C15 | −0.3 (5) | C19—C20—C33—C28 | 177.2 (3) |
C6—C1—C14—C15 | 179.6 (3) | C31—C32—C33—C20 | −179.1 (3) |
C12—C13—C14—C1 | 179.4 (3) | C31—C32—C33—C28 | 0.8 (5) |
C8—C13—C14—C1 | 0.3 (4) | C27—C28—C33—C20 | −0.4 (4) |
C12—C13—C14—C15 | −0.4 (4) | C29—C28—C33—C20 | 179.4 (3) |
C8—C13—C14—C15 | −179.5 (3) | C27—C28—C33—C32 | 179.7 (3) |
C16'—N1—C15—C14 | −64.1 (4) | C29—C28—C33—C32 | −0.5 (4) |
C19—N1—C15—C14 | 168.7 (2) | C16'—N1—C16—C17 | 26.3 (14) |
C16—N1—C15—C14 | −78.1 (6) | C15—N1—C16—C17 | 164.7 (7) |
C1—C14—C15—N1 | 110.1 (3) | C19—N1—C16—C17 | −78.8 (9) |
C13—C14—C15—N1 | −70.2 (3) | N1—C16—C17—C18 | −177.6 (9) |
C16'—N1—C19—C20 | 165.7 (4) | C15—N1—C16'—C17' | 157.9 (4) |
C15—N1—C19—C20 | −64.3 (4) | C19—N1—C16'—C17' | −74.7 (6) |
C16—N1—C19—C20 | −174.7 (6) | C16—N1—C16'—C17' | −156 (2) |
N1—C19—C20—C33 | 109.8 (3) | C18'—C17'—C16'—N1 | 175.5 (5) |