Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802009418/ob6119sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802009418/ob6119Isup2.hkl |
CCDC reference: 189887
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SHELXTL (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C34H26N2O | F(000) = 1008 |
Mr = 478.57 | Dx = 1.241 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 12.661 (5) Å | Cell parameters from 93 reflections |
b = 19.247 (7) Å | θ = 2.3–24.7° |
c = 11.010 (4) Å | µ = 0.08 mm−1 |
β = 107.273 (7)° | T = 293 K |
V = 2561.8 (16) Å3 | Plate, colorless |
Z = 4 | 0.35 × 0.25 × 0.15 mm |
Bruker CCD area-detector diffractometer | 4517 independent reflections |
Radiation source: fine-focus sealed tube | 1891 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.082 |
φ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −15→14 |
Tmin = 0.974, Tmax = 0.989 | k = −22→20 |
10446 measured reflections | l = −13→12 |
Refinement on F2 | H-atom parameters constrained |
Least-squares matrix: full | w = 1/[σ2(Fo2) + (0.038P)2] where P = (Fo2 + 2Fc2)/3 |
R[F2 > 2σ(F2)] = 0.047 | (Δ/σ)max < 0.001 |
wR(F2) = 0.115 | Δρmax = 0.16 e Å−3 |
S = 0.98 | Δρmin = −0.16 e Å−3 |
4517 reflections | Extinction correction: SHELXL97 |
335 parameters | Extinction coefficient: 0.0023 (4) |
0 restraints |
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) | |
O1 | 0.87292 (19) | 0.90551 (12) | 0.1137 (2) | 0.0540 (7) | 0.50 |
N1A | 0.87292 (19) | 0.90551 (12) | 0.1137 (2) | 0.0540 (7) | 0.50 |
N2 | 0.8346 (2) | 1.28815 (14) | −0.0255 (3) | 0.0629 (8) | |
N1 | 0.78546 (19) | 0.87502 (13) | 0.2529 (2) | 0.0595 (7) | 0.50 |
O1A | 0.78546 (19) | 0.87502 (13) | 0.2529 (2) | 0.0595 (7) | 0.50 |
C1 | 0.8093 (2) | 0.99903 (15) | 0.2248 (3) | 0.0449 (8) | |
H1 | 0.7789 | 1.0051 | 0.2962 | 0.054* | |
C2 | 0.9066 (2) | 1.05012 (14) | 0.2327 (3) | 0.0419 (8) | |
H2 | 0.9040 | 1.0879 | 0.2915 | 0.050* | |
C3 | 0.8477 (2) | 1.07406 (14) | 0.0953 (3) | 0.0427 (8) | |
H3 | 0.8776 | 1.0472 | 0.0374 | 0.051* | |
C4 | 0.7385 (2) | 1.03766 (14) | 0.1025 (3) | 0.0459 (8) | |
H4 | 0.7123 | 1.0047 | 0.0321 | 0.055* | |
C5 | 0.8259 (3) | 0.92571 (16) | 0.2008 (3) | 0.0505 (9) | |
C6 | 0.8618 (3) | 0.83397 (17) | 0.1102 (3) | 0.0494 (8) | |
C7 | 0.8953 (3) | 0.7853 (2) | 0.0375 (3) | 0.0723 (11) | |
H7 | 0.9344 | 0.7982 | −0.0183 | 0.087* | |
C8 | 0.8691 (3) | 0.7180 (2) | 0.0502 (4) | 0.0811 (12) | |
H8 | 0.8902 | 0.6842 | 0.0017 | 0.097* | |
C9 | 0.8124 (4) | 0.6987 (2) | 0.1331 (4) | 0.0838 (13) | |
H9 | 0.7949 | 0.6521 | 0.1388 | 0.101* | |
C10 | 0.7808 (3) | 0.7467 (2) | 0.2081 (4) | 0.0770 (12) | |
H10 | 0.7431 | 0.7337 | 0.2652 | 0.092* | |
C11 | 0.8076 (3) | 0.81485 (17) | 0.1947 (3) | 0.0516 (9) | |
C12 | 1.0231 (2) | 1.02363 (14) | 0.2637 (3) | 0.0387 (7) | |
C13 | 1.0917 (3) | 1.04226 (14) | 0.1924 (3) | 0.0469 (8) | |
H13 | 1.0651 | 1.0714 | 0.1226 | 0.056* | |
C14 | 1.1990 (3) | 1.01841 (14) | 0.2231 (3) | 0.0456 (8) | |
H14 | 1.2432 | 1.0321 | 0.1732 | 0.055* | |
C15 | 1.2436 (2) | 0.97474 (15) | 0.3259 (3) | 0.0411 (8) | |
C16 | 1.1735 (2) | 0.95591 (15) | 0.3978 (3) | 0.0483 (8) | |
H16 | 1.1996 | 0.9265 | 0.4673 | 0.058* | |
C17 | 1.0663 (2) | 0.98033 (16) | 0.3671 (3) | 0.0489 (8) | |
H17 | 1.0219 | 0.9674 | 0.4171 | 0.059* | |
C18 | 1.3561 (3) | 0.94607 (17) | 0.3537 (3) | 0.0452 (8) | |
C19 | 1.4403 (3) | 0.98439 (18) | 0.3288 (3) | 0.0644 (10) | |
H19 | 1.4265 | 1.0293 | 0.2971 | 0.077* | |
C20 | 1.5443 (3) | 0.9559 (3) | 0.3513 (4) | 0.0844 (13) | |
H20 | 1.5999 | 0.9818 | 0.3335 | 0.101* | |
C21 | 1.5670 (3) | 0.8908 (3) | 0.3986 (4) | 0.0865 (13) | |
H21 | 1.6373 | 0.8722 | 0.4121 | 0.104* | |
C22 | 1.4858 (3) | 0.8526 (2) | 0.4264 (3) | 0.0807 (12) | |
H22 | 1.5012 | 0.8083 | 0.4604 | 0.097* | |
C23 | 1.3811 (3) | 0.88034 (18) | 0.4037 (3) | 0.0624 (10) | |
H23 | 1.3264 | 0.8541 | 0.4226 | 0.075* | |
C24 | 0.6456 (2) | 1.08255 (15) | 0.1129 (3) | 0.0483 (8) | |
C25 | 0.6441 (3) | 1.11766 (16) | 0.2206 (3) | 0.0636 (10) | |
H25 | 0.7047 | 1.1148 | 0.2930 | 0.076* | |
C26 | 0.5538 (4) | 1.15730 (18) | 0.2236 (4) | 0.0845 (13) | |
H26 | 0.5537 | 1.1802 | 0.2979 | 0.101* | |
C27 | 0.4646 (3) | 1.1629 (2) | 0.1172 (6) | 0.0929 (15) | |
H27 | 0.4037 | 1.1895 | 0.1189 | 0.111* | |
C28 | 0.4657 (3) | 1.1295 (2) | 0.0098 (5) | 0.1088 (16) | |
H28 | 0.4056 | 1.1335 | −0.0630 | 0.131* | |
C29 | 0.5546 (3) | 1.08983 (19) | 0.0072 (4) | 0.0817 (12) | |
H29 | 0.5537 | 1.0672 | −0.0677 | 0.098* | |
C30 | 0.8444 (2) | 1.14866 (15) | 0.0578 (3) | 0.0418 (8) | |
C31 | 0.8907 (3) | 1.20190 (17) | 0.1389 (3) | 0.0554 (9) | |
H31 | 0.9268 | 1.1927 | 0.2240 | 0.066* | |
C32 | 0.8836 (3) | 1.26948 (18) | 0.0936 (4) | 0.0633 (10) | |
H32 | 0.9156 | 1.3043 | 0.1513 | 0.076* | |
C33 | 0.7899 (3) | 1.23608 (19) | −0.1024 (3) | 0.0673 (10) | |
H33 | 0.7536 | 1.2468 | −0.1869 | 0.081* | |
C34 | 0.7930 (3) | 1.16731 (17) | −0.0667 (3) | 0.0629 (10) | |
H34 | 0.7604 | 1.1335 | −0.1265 | 0.076* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0660 (18) | 0.0429 (15) | 0.0605 (17) | −0.0054 (13) | 0.0304 (14) | −0.0002 (13) |
N1A | 0.0660 (18) | 0.0429 (15) | 0.0605 (17) | −0.0054 (13) | 0.0304 (14) | −0.0002 (13) |
N2 | 0.071 (2) | 0.057 (2) | 0.056 (2) | 0.0052 (16) | 0.0112 (17) | 0.0032 (18) |
N1 | 0.0540 (17) | 0.0627 (18) | 0.0642 (18) | −0.0046 (14) | 0.0211 (14) | 0.0096 (15) |
O1A | 0.0540 (17) | 0.0627 (18) | 0.0642 (18) | −0.0046 (14) | 0.0211 (14) | 0.0096 (15) |
C1 | 0.040 (2) | 0.053 (2) | 0.0403 (19) | 0.0039 (16) | 0.0107 (16) | 0.0034 (16) |
C2 | 0.044 (2) | 0.0433 (19) | 0.0364 (19) | 0.0090 (16) | 0.0094 (15) | 0.0010 (15) |
C3 | 0.044 (2) | 0.045 (2) | 0.0374 (19) | 0.0081 (15) | 0.0093 (15) | 0.0002 (15) |
C4 | 0.046 (2) | 0.0488 (19) | 0.0380 (19) | 0.0032 (17) | 0.0052 (16) | −0.0034 (16) |
C5 | 0.043 (2) | 0.047 (2) | 0.057 (2) | 0.0008 (17) | 0.0089 (18) | 0.0072 (19) |
C6 | 0.048 (2) | 0.042 (2) | 0.054 (2) | 0.0041 (17) | 0.0103 (18) | 0.0047 (19) |
C7 | 0.082 (3) | 0.063 (3) | 0.077 (3) | 0.001 (2) | 0.031 (2) | −0.010 (2) |
C8 | 0.104 (4) | 0.054 (3) | 0.071 (3) | 0.014 (2) | 0.005 (3) | −0.005 (2) |
C9 | 0.100 (4) | 0.049 (3) | 0.076 (3) | −0.008 (2) | −0.014 (3) | 0.010 (2) |
C10 | 0.087 (3) | 0.064 (3) | 0.073 (3) | −0.016 (2) | 0.013 (2) | 0.016 (2) |
C11 | 0.054 (2) | 0.043 (2) | 0.052 (2) | −0.0011 (18) | 0.0074 (18) | 0.0080 (18) |
C12 | 0.040 (2) | 0.0399 (18) | 0.0353 (18) | 0.0020 (15) | 0.0098 (15) | −0.0020 (15) |
C13 | 0.052 (2) | 0.0428 (19) | 0.045 (2) | 0.0054 (17) | 0.0133 (17) | 0.0081 (16) |
C14 | 0.046 (2) | 0.0454 (19) | 0.048 (2) | 0.0012 (16) | 0.0173 (17) | 0.0023 (17) |
C15 | 0.041 (2) | 0.0424 (19) | 0.0380 (19) | −0.0006 (15) | 0.0084 (16) | −0.0033 (16) |
C16 | 0.045 (2) | 0.059 (2) | 0.0383 (19) | 0.0075 (17) | 0.0078 (17) | 0.0044 (17) |
C17 | 0.043 (2) | 0.067 (2) | 0.0384 (19) | 0.0026 (17) | 0.0138 (16) | 0.0058 (17) |
C18 | 0.041 (2) | 0.056 (2) | 0.0377 (19) | 0.0023 (18) | 0.0104 (16) | −0.0056 (17) |
C19 | 0.047 (2) | 0.084 (3) | 0.062 (2) | 0.003 (2) | 0.0161 (19) | 0.006 (2) |
C20 | 0.044 (3) | 0.137 (4) | 0.075 (3) | 0.007 (3) | 0.021 (2) | 0.013 (3) |
C21 | 0.054 (3) | 0.132 (4) | 0.074 (3) | 0.033 (3) | 0.019 (2) | 0.008 (3) |
C22 | 0.071 (3) | 0.084 (3) | 0.084 (3) | 0.029 (3) | 0.019 (3) | 0.009 (2) |
C23 | 0.047 (2) | 0.067 (3) | 0.072 (3) | 0.0091 (19) | 0.0156 (19) | 0.003 (2) |
C24 | 0.038 (2) | 0.048 (2) | 0.054 (2) | 0.0020 (16) | 0.0058 (17) | 0.0002 (18) |
C25 | 0.059 (3) | 0.067 (2) | 0.061 (3) | 0.016 (2) | 0.013 (2) | −0.006 (2) |
C26 | 0.092 (4) | 0.071 (3) | 0.100 (4) | 0.021 (3) | 0.044 (3) | −0.004 (2) |
C27 | 0.047 (3) | 0.079 (3) | 0.153 (5) | 0.016 (2) | 0.028 (3) | 0.008 (3) |
C28 | 0.050 (3) | 0.112 (4) | 0.133 (5) | 0.024 (3) | −0.021 (3) | −0.024 (3) |
C29 | 0.057 (3) | 0.092 (3) | 0.076 (3) | 0.020 (2) | −0.012 (2) | −0.020 (2) |
C30 | 0.038 (2) | 0.050 (2) | 0.037 (2) | 0.0055 (15) | 0.0099 (16) | −0.0025 (17) |
C31 | 0.061 (2) | 0.053 (2) | 0.044 (2) | 0.0065 (18) | 0.0031 (18) | 0.0017 (19) |
C32 | 0.066 (3) | 0.051 (2) | 0.063 (3) | 0.0023 (19) | 0.004 (2) | −0.006 (2) |
C33 | 0.092 (3) | 0.063 (3) | 0.038 (2) | 0.010 (2) | 0.005 (2) | 0.007 (2) |
C34 | 0.088 (3) | 0.051 (2) | 0.039 (2) | 0.0031 (19) | 0.003 (2) | 0.0023 (19) |
O1—C5 | 1.329 (3) | C15—C18 | 1.472 (4) |
O1—C6 | 1.384 (3) | C16—C17 | 1.380 (4) |
N2—C32 | 1.323 (4) | C16—H16 | 0.9300 |
N2—C33 | 1.325 (4) | C17—H17 | 0.9300 |
N1—C5 | 1.310 (3) | C18—C23 | 1.379 (4) |
N1—C11 | 1.392 (3) | C18—C19 | 1.388 (4) |
C1—C5 | 1.462 (4) | C19—C20 | 1.380 (4) |
C1—C2 | 1.558 (4) | C19—H19 | 0.9300 |
C1—C4 | 1.566 (4) | C20—C21 | 1.353 (5) |
C1—H1 | 0.9800 | C20—H20 | 0.9300 |
C2—C12 | 1.502 (4) | C21—C22 | 1.370 (5) |
C2—C3 | 1.545 (4) | C21—H21 | 0.9300 |
C2—H2 | 0.9800 | C22—C23 | 1.381 (4) |
C3—C30 | 1.491 (4) | C22—H22 | 0.9300 |
C3—C4 | 1.572 (4) | C23—H23 | 0.9300 |
C3—H3 | 0.9800 | C24—C25 | 1.370 (4) |
C4—C24 | 1.491 (4) | C24—C29 | 1.381 (4) |
C4—H4 | 0.9800 | C25—C26 | 1.382 (4) |
C6—C11 | 1.360 (4) | C25—H25 | 0.9300 |
C6—C7 | 1.378 (4) | C26—C27 | 1.368 (5) |
C7—C8 | 1.355 (4) | C26—H26 | 0.9300 |
C7—H7 | 0.9300 | C27—C28 | 1.350 (5) |
C8—C9 | 1.369 (5) | C27—H27 | 0.9300 |
C8—H8 | 0.9300 | C28—C29 | 1.367 (5) |
C9—C10 | 1.376 (5) | C28—H28 | 0.9300 |
C9—H9 | 0.9300 | C29—H29 | 0.9300 |
C10—C11 | 1.373 (4) | C30—C31 | 1.371 (4) |
C10—H10 | 0.9300 | C30—C34 | 1.379 (4) |
C12—C13 | 1.380 (3) | C31—C32 | 1.386 (4) |
C12—C17 | 1.385 (4) | C31—H31 | 0.9300 |
C13—C14 | 1.378 (4) | C32—H32 | 0.9300 |
C13—H13 | 0.9300 | C33—C34 | 1.378 (4) |
C14—C15 | 1.388 (4) | C33—H33 | 0.9300 |
C14—H14 | 0.9300 | C34—H34 | 0.9300 |
C15—C16 | 1.401 (4) | ||
C5—O1—C6 | 104.3 (3) | C16—C15—C18 | 121.4 (3) |
C32—N2—C33 | 114.4 (3) | C17—C16—C15 | 121.0 (3) |
C5—N1—C11 | 105.1 (3) | C17—C16—H16 | 119.5 |
C5—C1—C2 | 117.8 (3) | C15—C16—H16 | 119.5 |
C5—C1—C4 | 112.3 (2) | C16—C17—C12 | 121.7 (3) |
C2—C1—C4 | 89.4 (2) | C16—C17—H17 | 119.1 |
C5—C1—H1 | 111.8 | C12—C17—H17 | 119.1 |
C2—C1—H1 | 111.8 | C23—C18—C19 | 117.8 (3) |
C4—C1—H1 | 111.8 | C23—C18—C15 | 121.4 (3) |
C12—C2—C3 | 118.7 (2) | C19—C18—C15 | 120.8 (3) |
C12—C2—C1 | 120.4 (2) | C20—C19—C18 | 120.1 (3) |
C3—C2—C1 | 89.4 (2) | C20—C19—H19 | 120.0 |
C12—C2—H2 | 108.9 | C18—C19—H19 | 120.0 |
C3—C2—H2 | 108.9 | C21—C20—C19 | 121.2 (4) |
C1—C2—H2 | 108.9 | C21—C20—H20 | 119.4 |
C30—C3—C2 | 121.6 (3) | C19—C20—H20 | 119.4 |
C30—C3—C4 | 119.4 (2) | C20—C21—C22 | 119.7 (4) |
C2—C3—C4 | 89.6 (2) | C20—C21—H21 | 120.2 |
C30—C3—H3 | 108.2 | C22—C21—H21 | 120.2 |
C2—C3—H3 | 108.2 | C21—C22—C23 | 119.7 (4) |
C4—C3—H3 | 108.2 | C21—C22—H22 | 120.1 |
C24—C4—C1 | 118.2 (2) | C23—C22—H22 | 120.1 |
C24—C4—C3 | 118.1 (2) | C18—C23—C22 | 121.4 (3) |
C1—C4—C3 | 88.2 (2) | C18—C23—H23 | 119.3 |
C24—C4—H4 | 110.2 | C22—C23—H23 | 119.3 |
C1—C4—H4 | 110.2 | C25—C24—C29 | 117.2 (3) |
C3—C4—H4 | 110.2 | C25—C24—C4 | 124.5 (3) |
N1—C5—O1 | 114.5 (3) | C29—C24—C4 | 118.3 (3) |
N1—C5—C1 | 123.0 (3) | C24—C25—C26 | 121.1 (3) |
O1—C5—C1 | 122.1 (3) | C24—C25—H25 | 119.4 |
C11—C6—C7 | 121.2 (3) | C26—C25—H25 | 119.4 |
C11—C6—O1 | 108.6 (3) | C27—C26—C25 | 120.1 (4) |
C7—C6—O1 | 130.2 (3) | C27—C26—H26 | 120.0 |
C8—C7—C6 | 117.6 (4) | C25—C26—H26 | 120.0 |
C8—C7—H7 | 121.2 | C28—C27—C26 | 119.5 (4) |
C6—C7—H7 | 121.2 | C28—C27—H27 | 120.3 |
C7—C8—C9 | 121.4 (4) | C26—C27—H27 | 120.3 |
C7—C8—H8 | 119.3 | C27—C28—C29 | 120.5 (4) |
C9—C8—H8 | 119.3 | C27—C28—H28 | 119.8 |
C8—C9—C10 | 121.4 (4) | C29—C28—H28 | 119.8 |
C8—C9—H9 | 119.3 | C28—C29—C24 | 121.7 (4) |
C10—C9—H9 | 119.3 | C28—C29—H29 | 119.2 |
C11—C10—C9 | 116.9 (4) | C24—C29—H29 | 119.2 |
C11—C10—H10 | 121.6 | C31—C30—C34 | 115.9 (3) |
C9—C10—H10 | 121.6 | C31—C30—C3 | 124.6 (3) |
C6—C11—C10 | 121.5 (4) | C34—C30—C3 | 119.5 (3) |
C6—C11—N1 | 107.5 (3) | C30—C31—C32 | 119.8 (3) |
C10—C11—N1 | 130.9 (4) | C30—C31—H31 | 120.1 |
C13—C12—C17 | 117.5 (3) | C32—C31—H31 | 120.1 |
C13—C12—C2 | 121.6 (3) | N2—C32—C31 | 124.9 (3) |
C17—C12—C2 | 120.9 (3) | N2—C32—H32 | 117.5 |
C14—C13—C12 | 121.0 (3) | C31—C32—H32 | 117.5 |
C14—C13—H13 | 119.5 | N2—C33—C34 | 125.0 (3) |
C12—C13—H13 | 119.5 | N2—C33—H33 | 117.5 |
C13—C14—C15 | 122.3 (3) | C34—C33—H33 | 117.5 |
C13—C14—H14 | 118.9 | C33—C34—C30 | 119.9 (3) |
C15—C14—H14 | 118.9 | C33—C34—H34 | 120.1 |
C14—C15—C16 | 116.4 (3) | C30—C34—H34 | 120.1 |
C14—C15—C18 | 122.0 (3) | ||
C5—C1—C2—C12 | −22.3 (4) | C12—C13—C14—C15 | 0.2 (4) |
C4—C1—C2—C12 | −137.4 (3) | C13—C14—C15—C16 | −0.1 (4) |
C5—C1—C2—C3 | 101.0 (3) | C13—C14—C15—C18 | 176.3 (3) |
C4—C1—C2—C3 | −14.0 (2) | C14—C15—C16—C17 | −0.4 (4) |
C12—C2—C3—C30 | −96.4 (3) | C18—C15—C16—C17 | −176.7 (3) |
C1—C2—C3—C30 | 138.8 (3) | C15—C16—C17—C12 | 0.7 (4) |
C12—C2—C3—C4 | 138.7 (3) | C13—C12—C17—C16 | −0.6 (4) |
C1—C2—C3—C4 | 14.0 (2) | C2—C12—C17—C16 | −179.5 (3) |
C5—C1—C4—C24 | 132.7 (3) | C14—C15—C18—C23 | −145.3 (3) |
C2—C1—C4—C24 | −107.4 (3) | C16—C15—C18—C23 | 30.8 (4) |
C5—C1—C4—C3 | −106.2 (3) | C14—C15—C18—C19 | 34.0 (4) |
C2—C1—C4—C3 | 13.8 (2) | C16—C15—C18—C19 | −149.9 (3) |
C30—C3—C4—C24 | −19.4 (4) | C23—C18—C19—C20 | 1.6 (5) |
C2—C3—C4—C24 | 107.3 (3) | C15—C18—C19—C20 | −177.7 (3) |
C30—C3—C4—C1 | −140.6 (3) | C18—C19—C20—C21 | −0.6 (6) |
C2—C3—C4—C1 | −13.9 (2) | C19—C20—C21—C22 | −0.8 (6) |
C11—N1—C5—O1 | 0.0 (4) | C20—C21—C22—C23 | 1.2 (6) |
C11—N1—C5—C1 | 172.9 (3) | C19—C18—C23—C22 | −1.2 (5) |
C6—O1—C5—N1 | −0.3 (4) | C15—C18—C23—C22 | 178.1 (3) |
C6—O1—C5—C1 | −173.4 (3) | C21—C22—C23—C18 | −0.2 (5) |
C2—C1—C5—N1 | 143.5 (3) | C1—C4—C24—C25 | 30.5 (4) |
C4—C1—C5—N1 | −114.8 (3) | C3—C4—C24—C25 | −73.7 (4) |
C2—C1—C5—O1 | −44.0 (4) | C1—C4—C24—C29 | −149.7 (3) |
C4—C1—C5—O1 | 57.7 (4) | C3—C4—C24—C29 | 106.1 (3) |
C5—O1—C6—C11 | 0.6 (3) | C29—C24—C25—C26 | 1.4 (5) |
C5—O1—C6—C7 | −180.0 (3) | C4—C24—C25—C26 | −178.8 (3) |
C11—C6—C7—C8 | 2.1 (5) | C24—C25—C26—C27 | −1.0 (6) |
O1—C6—C7—C8 | −177.3 (3) | C25—C26—C27—C28 | −0.1 (6) |
C6—C7—C8—C9 | −0.6 (6) | C26—C27—C28—C29 | 0.6 (7) |
C7—C8—C9—C10 | −0.9 (6) | C27—C28—C29—C24 | −0.1 (7) |
C8—C9—C10—C11 | 0.8 (6) | C25—C24—C29—C28 | −0.9 (6) |
C7—C6—C11—C10 | −2.2 (5) | C4—C24—C29—C28 | 179.3 (4) |
O1—C6—C11—C10 | 177.4 (3) | C2—C3—C30—C31 | −0.7 (4) |
C7—C6—C11—N1 | 179.9 (3) | C4—C3—C30—C31 | 109.0 (3) |
O1—C6—C11—N1 | −0.6 (4) | C2—C3—C30—C34 | 178.6 (3) |
C9—C10—C11—C6 | 0.7 (5) | C4—C3—C30—C34 | −71.7 (4) |
C9—C10—C11—N1 | 178.1 (3) | C34—C30—C31—C32 | 0.2 (4) |
C5—N1—C11—C6 | 0.4 (3) | C3—C30—C31—C32 | 179.5 (3) |
C5—N1—C11—C10 | −177.3 (3) | C33—N2—C32—C31 | 0.5 (5) |
C3—C2—C12—C13 | 23.7 (4) | C30—C31—C32—N2 | −0.2 (5) |
C1—C2—C12—C13 | 131.6 (3) | C32—N2—C33—C34 | −0.8 (5) |
C3—C2—C12—C17 | −157.5 (3) | N2—C33—C34—C30 | 0.8 (5) |
C1—C2—C12—C17 | −49.6 (4) | C31—C30—C34—C33 | −0.4 (5) |
C17—C12—C13—C14 | 0.1 (4) | C3—C30—C34—C33 | −179.8 (3) |
C2—C12—C13—C14 | 179.0 (3) |