Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014171/lh2343sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014171/lh2343Isup2.hkl |
CCDC reference: 647270
Data collection: CrystalClear (Rigaku, 2004); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C14H17BrINO | Z = 4 |
Mr = 422.10 | F(000) = 816 |
Triclinic, P1 | Dx = 1.888 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.0837 (10) Å | Cell parameters from 4848 reflections |
b = 12.2016 (17) Å | θ = 2.3–28.2° |
c = 13.702 (2) Å | µ = 4.84 mm−1 |
α = 88.495 (8)° | T = 93 K |
β = 84.782 (8)° | Prism, colourless |
γ = 79.050 (8)° | 0.30 × 0.20 × 0.10 mm |
V = 1484.8 (3) Å3 |
Rigaku Mercury CCD diffractometer | 4997 independent reflections |
Radiation source: rotating anode | 4376 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.026 |
ω and φ scans | θmax = 25.4°, θmin = 2.3° |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2004) | h = −10→10 |
Tmin = 0.325, Tmax = 0.643 | k = −14→14 |
9422 measured reflections | l = −12→16 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.108 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.052P)2 + 3.3908P] where P = (Fo2 + 2Fc2)/3 |
4997 reflections | (Δ/σ)max < 0.001 |
327 parameters | Δρmax = 1.08 e Å−3 |
0 restraints | Δρmin = −1.14 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 | ||
C1 | 0.1047 (6) | 0.8225 (5) | 0.2585 (4) | 0.0142 (12) | |
C2 | 0.2599 (6) | 0.7959 (5) | 0.2350 (4) | 0.0169 (12) | |
H2 | 0.3194 | 0.8506 | 0.2431 | 0.020* | |
C3 | 0.3291 (7) | 0.6917 (5) | 0.2003 (4) | 0.0195 (13) | |
H3 | 0.4351 | 0.6743 | 0.1858 | 0.023* | |
C4 | 0.2408 (6) | 0.6130 (5) | 0.1870 (4) | 0.0165 (12) | |
C5 | 0.0868 (6) | 0.6385 (5) | 0.2065 (4) | 0.0166 (12) | |
H5 | 0.0283 | 0.5837 | 0.1961 | 0.020* | |
C6 | 0.0152 (6) | 0.7434 (5) | 0.2415 (4) | 0.0152 (12) | |
C7 | −0.1862 (7) | 0.7457 (6) | 0.3747 (4) | 0.0272 (15) | |
H7A | −0.1184 | 0.7743 | 0.4151 | 0.041* | |
H7B | −0.1798 | 0.6656 | 0.3874 | 0.041* | |
H7C | −0.2897 | 0.7849 | 0.3911 | 0.041* | |
C8 | −0.2533 (6) | 0.7908 (4) | 0.2075 (4) | 0.0145 (12) | |
C9 | −0.2122 (6) | 0.8111 (5) | 0.1002 (4) | 0.0164 (12) | |
H9 | −0.1119 | 0.7639 | 0.0803 | 0.020* | |
C10 | −0.3296 (7) | 0.7807 (5) | 0.0369 (4) | 0.0216 (13) | |
H10A | −0.3304 | 0.6999 | 0.0443 | 0.026* | |
H10B | −0.4306 | 0.8220 | 0.0607 | 0.026* | |
C11 | −0.2977 (7) | 0.8082 (5) | −0.0712 (5) | 0.0230 (14) | |
H11A | −0.3791 | 0.7912 | −0.1082 | 0.028* | |
H11B | −0.2019 | 0.7609 | −0.0971 | 0.028* | |
C12 | −0.2871 (7) | 0.9308 (5) | −0.0862 (5) | 0.0236 (14) | |
H12A | −0.3868 | 0.9779 | −0.0683 | 0.028* | |
H12B | −0.2586 | 0.9447 | −0.1563 | 0.028* | |
C13 | −0.1714 (7) | 0.9633 (5) | −0.0242 (4) | 0.0241 (14) | |
H13A | −0.0697 | 0.9235 | −0.0482 | 0.029* | |
H13B | −0.1730 | 1.0445 | −0.0315 | 0.029* | |
C14 | −0.2021 (7) | 0.9353 (5) | 0.0834 (4) | 0.0222 (13) | |
H14A | −0.2978 | 0.9825 | 0.1095 | 0.027* | |
H14B | −0.1206 | 0.9529 | 0.1202 | 0.027* | |
N1 | −0.1417 (5) | 0.7643 (4) | 0.2698 (3) | 0.0169 (11) | |
O1 | −0.3858 (4) | 0.8035 (3) | 0.2407 (3) | 0.0201 (9) | |
Br1 | 0.33296 (7) | 0.46748 (5) | 0.14507 (5) | 0.02437 (17) | |
I1 | 0.01013 (4) | 0.97811 (3) | 0.31835 (3) | 0.02065 (13) | |
C15 | 0.4082 (6) | 0.1997 (5) | 0.3629 (4) | 0.0178 (13) | |
C16 | 0.2544 (6) | 0.2398 (5) | 0.3573 (4) | 0.0171 (12) | |
H16 | 0.1940 | 0.1922 | 0.3342 | 0.021* | |
C17 | 0.1892 (6) | 0.3463 (5) | 0.3845 (4) | 0.0191 (13) | |
H17 | 0.0844 | 0.3724 | 0.3808 | 0.023* | |
C18 | 0.2785 (6) | 0.4159 (5) | 0.4177 (4) | 0.0169 (12) | |
C19 | 0.4316 (6) | 0.3777 (5) | 0.4250 (4) | 0.0173 (12) | |
H19 | 0.4913 | 0.4254 | 0.4488 | 0.021* | |
C20 | 0.4957 (6) | 0.2709 (5) | 0.3977 (4) | 0.0156 (12) | |
C21 | 0.6833 (7) | 0.1716 (6) | 0.5044 (5) | 0.0257 (14) | |
H21A | 0.6252 | 0.1115 | 0.5133 | 0.039* | |
H21B | 0.6547 | 0.2240 | 0.5588 | 0.039* | |
H21C | 0.7910 | 0.1397 | 0.5030 | 0.039* | |
C22 | 0.7693 (6) | 0.2537 (4) | 0.3503 (4) | 0.0153 (12) | |
C23 | 0.7348 (6) | 0.3136 (5) | 0.2536 (4) | 0.0178 (13) | |
H23 | 0.6244 | 0.3235 | 0.2465 | 0.021* | |
C24 | 0.7794 (7) | 0.4283 (5) | 0.2539 (5) | 0.0239 (14) | |
H24A | 0.8840 | 0.4194 | 0.2722 | 0.029* | |
H24B | 0.7129 | 0.4755 | 0.3040 | 0.029* | |
C25 | 0.7683 (7) | 0.4870 (5) | 0.1540 (5) | 0.0269 (15) | |
H25A | 0.6620 | 0.5037 | 0.1385 | 0.032* | |
H25B | 0.8043 | 0.5585 | 0.1560 | 0.032* | |
C26 | 0.8631 (7) | 0.4128 (6) | 0.0748 (5) | 0.0336 (17) | |
H26A | 0.8551 | 0.4510 | 0.0104 | 0.040* | |
H26B | 0.9701 | 0.3987 | 0.0889 | 0.040* | |
C27 | 0.8091 (7) | 0.3021 (5) | 0.0714 (5) | 0.0256 (14) | |
H27A | 0.8705 | 0.2549 | 0.0193 | 0.031* | |
H27B | 0.7030 | 0.3162 | 0.0554 | 0.031* | |
C28 | 0.8219 (7) | 0.2409 (5) | 0.1700 (5) | 0.0232 (14) | |
H28A | 0.9292 | 0.2204 | 0.1828 | 0.028* | |
H28B | 0.7817 | 0.1711 | 0.1673 | 0.028* | |
N2 | 0.6521 (5) | 0.2304 (4) | 0.4119 (3) | 0.0166 (11) | |
O2 | 0.8991 (4) | 0.2255 (3) | 0.3722 (3) | 0.0195 (9) | |
Br2 | 0.19102 (6) | 0.56281 (5) | 0.46021 (5) | 0.02319 (16) | |
I2 | 0.50497 (4) | 0.03808 (3) | 0.31934 (3) | 0.02059 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.015 (3) | 0.017 (3) | 0.010 (3) | −0.001 (2) | −0.004 (2) | 0.002 (2) |
C2 | 0.016 (3) | 0.018 (3) | 0.020 (3) | −0.008 (2) | −0.006 (2) | 0.000 (2) |
C3 | 0.021 (3) | 0.019 (3) | 0.020 (3) | −0.007 (2) | −0.002 (3) | −0.003 (3) |
C4 | 0.019 (3) | 0.013 (3) | 0.016 (3) | 0.001 (2) | −0.004 (2) | 0.002 (2) |
C5 | 0.015 (3) | 0.020 (3) | 0.017 (3) | −0.007 (2) | −0.005 (2) | 0.000 (2) |
C6 | 0.012 (3) | 0.022 (3) | 0.012 (3) | −0.003 (2) | −0.004 (2) | 0.004 (2) |
C7 | 0.017 (3) | 0.045 (4) | 0.020 (3) | −0.007 (3) | −0.001 (3) | 0.009 (3) |
C8 | 0.014 (3) | 0.013 (3) | 0.017 (3) | −0.004 (2) | −0.002 (2) | −0.003 (2) |
C9 | 0.015 (3) | 0.018 (3) | 0.016 (3) | −0.002 (2) | −0.003 (2) | −0.002 (2) |
C10 | 0.026 (3) | 0.017 (3) | 0.026 (3) | −0.009 (2) | −0.011 (3) | 0.000 (3) |
C11 | 0.019 (3) | 0.026 (3) | 0.024 (4) | −0.001 (3) | −0.007 (3) | −0.001 (3) |
C12 | 0.025 (3) | 0.026 (3) | 0.021 (3) | −0.007 (3) | −0.004 (3) | 0.005 (3) |
C13 | 0.030 (4) | 0.022 (3) | 0.021 (3) | −0.008 (3) | −0.002 (3) | −0.001 (3) |
C14 | 0.028 (3) | 0.022 (3) | 0.020 (3) | −0.014 (3) | −0.002 (3) | −0.002 (3) |
N1 | 0.012 (2) | 0.023 (3) | 0.016 (3) | −0.0031 (19) | 0.000 (2) | 0.003 (2) |
O1 | 0.013 (2) | 0.024 (2) | 0.024 (2) | −0.0059 (16) | 0.0004 (18) | −0.0017 (18) |
Br1 | 0.0206 (3) | 0.0192 (3) | 0.0324 (4) | 0.0002 (2) | −0.0040 (3) | −0.0068 (3) |
I1 | 0.0196 (2) | 0.0188 (2) | 0.0233 (2) | −0.00164 (15) | −0.00381 (17) | −0.00248 (17) |
C15 | 0.017 (3) | 0.026 (3) | 0.011 (3) | −0.006 (2) | 0.000 (2) | −0.002 (2) |
C16 | 0.014 (3) | 0.020 (3) | 0.019 (3) | −0.006 (2) | −0.002 (2) | 0.003 (2) |
C17 | 0.008 (3) | 0.031 (3) | 0.018 (3) | −0.003 (2) | −0.002 (2) | −0.002 (3) |
C18 | 0.016 (3) | 0.022 (3) | 0.012 (3) | −0.003 (2) | 0.003 (2) | 0.002 (2) |
C19 | 0.021 (3) | 0.018 (3) | 0.014 (3) | −0.009 (2) | 0.000 (2) | −0.001 (2) |
C20 | 0.011 (3) | 0.019 (3) | 0.017 (3) | −0.005 (2) | 0.000 (2) | 0.003 (2) |
C21 | 0.024 (3) | 0.035 (4) | 0.019 (3) | −0.007 (3) | −0.003 (3) | 0.010 (3) |
C22 | 0.013 (3) | 0.011 (3) | 0.024 (3) | −0.005 (2) | −0.004 (2) | −0.004 (2) |
C23 | 0.014 (3) | 0.017 (3) | 0.023 (3) | −0.005 (2) | 0.003 (2) | 0.000 (2) |
C24 | 0.031 (4) | 0.015 (3) | 0.029 (4) | −0.010 (2) | −0.010 (3) | 0.007 (3) |
C25 | 0.032 (4) | 0.015 (3) | 0.036 (4) | −0.006 (3) | −0.012 (3) | 0.008 (3) |
C26 | 0.023 (4) | 0.044 (4) | 0.033 (4) | −0.007 (3) | −0.008 (3) | 0.021 (3) |
C27 | 0.028 (3) | 0.028 (4) | 0.018 (3) | −0.001 (3) | 0.002 (3) | 0.000 (3) |
C28 | 0.026 (3) | 0.015 (3) | 0.026 (4) | −0.001 (2) | 0.004 (3) | 0.004 (3) |
N2 | 0.015 (3) | 0.021 (3) | 0.015 (3) | −0.004 (2) | −0.003 (2) | 0.001 (2) |
O2 | 0.014 (2) | 0.019 (2) | 0.027 (2) | −0.0049 (16) | −0.0060 (18) | 0.0018 (18) |
Br2 | 0.0194 (3) | 0.0220 (3) | 0.0270 (4) | 0.0006 (2) | −0.0033 (3) | −0.0068 (3) |
I2 | 0.0189 (2) | 0.0203 (2) | 0.0233 (2) | −0.00522 (15) | −0.00136 (16) | −0.00349 (17) |
C1—C2 | 1.395 (8) | C15—C16 | 1.398 (8) |
C1—C6 | 1.412 (8) | C15—C20 | 1.403 (8) |
C1—I1 | 2.085 (6) | C15—I2 | 2.080 (6) |
C2—C3 | 1.382 (8) | C16—C17 | 1.368 (8) |
C2—H2 | 0.9500 | C16—H16 | 0.9500 |
C3—C4 | 1.388 (8) | C17—C18 | 1.391 (8) |
C3—H3 | 0.9500 | C17—H17 | 0.9500 |
C4—C5 | 1.377 (8) | C18—C19 | 1.392 (8) |
C4—Br1 | 1.894 (5) | C18—Br2 | 1.901 (6) |
C5—C6 | 1.397 (8) | C19—C20 | 1.368 (8) |
C5—H5 | 0.9500 | C19—H19 | 0.9500 |
C6—N1 | 1.419 (7) | C20—N2 | 1.442 (7) |
C7—N1 | 1.481 (7) | C21—N2 | 1.464 (7) |
C7—H7A | 0.9800 | C21—H21A | 0.9800 |
C7—H7B | 0.9800 | C21—H21B | 0.9800 |
C7—H7C | 0.9800 | C21—H21C | 0.9800 |
C8—O1 | 1.230 (7) | C22—O2 | 1.226 (7) |
C8—N1 | 1.371 (7) | C22—N2 | 1.365 (7) |
C8—C9 | 1.509 (8) | C22—C23 | 1.526 (8) |
C9—C10 | 1.536 (8) | C23—C24 | 1.529 (8) |
C9—C14 | 1.546 (8) | C23—C28 | 1.532 (8) |
C9—H9 | 1.0000 | C23—H23 | 1.0000 |
C10—C11 | 1.524 (9) | C24—C25 | 1.531 (9) |
C10—H10A | 0.9900 | C24—H24A | 0.9900 |
C10—H10B | 0.9900 | C24—H24B | 0.9900 |
C11—C12 | 1.524 (8) | C25—C26 | 1.525 (10) |
C11—H11A | 0.9900 | C25—H25A | 0.9900 |
C11—H11B | 0.9900 | C25—H25B | 0.9900 |
C12—C13 | 1.525 (8) | C26—C27 | 1.524 (9) |
C12—H12A | 0.9900 | C26—H26A | 0.9900 |
C12—H12B | 0.9900 | C26—H26B | 0.9900 |
C13—C14 | 1.518 (8) | C27—C28 | 1.530 (8) |
C13—H13A | 0.9900 | C27—H27A | 0.9900 |
C13—H13B | 0.9900 | C27—H27B | 0.9900 |
C14—H14A | 0.9900 | C28—H28A | 0.9900 |
C14—H14B | 0.9900 | C28—H28B | 0.9900 |
C2—C1—C6 | 119.2 (5) | C16—C15—C20 | 118.7 (5) |
C2—C1—I1 | 119.3 (4) | C16—C15—I2 | 120.5 (4) |
C6—C1—I1 | 121.5 (4) | C20—C15—I2 | 120.8 (4) |
C3—C2—C1 | 121.5 (5) | C17—C16—C15 | 121.3 (6) |
C3—C2—H2 | 119.2 | C17—C16—H16 | 119.4 |
C1—C2—H2 | 119.2 | C15—C16—H16 | 119.4 |
C2—C3—C4 | 118.8 (5) | C16—C17—C18 | 119.1 (5) |
C2—C3—H3 | 120.6 | C16—C17—H17 | 120.5 |
C4—C3—H3 | 120.6 | C18—C17—H17 | 120.5 |
C5—C4—C3 | 120.8 (5) | C17—C18—C19 | 120.8 (5) |
C5—C4—Br1 | 119.3 (4) | C17—C18—Br2 | 120.3 (4) |
C3—C4—Br1 | 119.8 (4) | C19—C18—Br2 | 118.8 (4) |
C4—C5—C6 | 121.1 (5) | C20—C19—C18 | 119.7 (5) |
C4—C5—H5 | 119.5 | C20—C19—H19 | 120.2 |
C6—C5—H5 | 119.5 | C18—C19—H19 | 120.2 |
C5—C6—C1 | 118.4 (5) | C19—C20—C15 | 120.5 (5) |
C5—C6—N1 | 120.1 (5) | C19—C20—N2 | 118.9 (5) |
C1—C6—N1 | 121.0 (5) | C15—C20—N2 | 120.5 (5) |
N1—C7—H7A | 109.5 | N2—C21—H21A | 109.5 |
N1—C7—H7B | 109.5 | N2—C21—H21B | 109.5 |
H7A—C7—H7B | 109.5 | H21A—C21—H21B | 109.5 |
N1—C7—H7C | 109.5 | N2—C21—H21C | 109.5 |
H7A—C7—H7C | 109.5 | H21A—C21—H21C | 109.5 |
H7B—C7—H7C | 109.5 | H21B—C21—H21C | 109.5 |
O1—C8—N1 | 119.5 (5) | O2—C22—N2 | 120.4 (5) |
O1—C8—C9 | 120.8 (5) | O2—C22—C23 | 121.1 (5) |
N1—C8—C9 | 119.6 (5) | N2—C22—C23 | 118.4 (5) |
C8—C9—C10 | 111.0 (5) | C22—C23—C24 | 109.1 (5) |
C8—C9—C14 | 109.5 (5) | C22—C23—C28 | 108.2 (5) |
C10—C9—C14 | 109.5 (5) | C24—C23—C28 | 111.7 (5) |
C8—C9—H9 | 109.0 | C22—C23—H23 | 109.2 |
C10—C9—H9 | 109.0 | C24—C23—H23 | 109.2 |
C14—C9—H9 | 109.0 | C28—C23—H23 | 109.2 |
C11—C10—C9 | 112.3 (5) | C23—C24—C25 | 112.2 (5) |
C11—C10—H10A | 109.1 | C23—C24—H24A | 109.2 |
C9—C10—H10A | 109.1 | C25—C24—H24A | 109.2 |
C11—C10—H10B | 109.1 | C23—C24—H24B | 109.2 |
C9—C10—H10B | 109.1 | C25—C24—H24B | 109.2 |
H10A—C10—H10B | 107.9 | H24A—C24—H24B | 107.9 |
C10—C11—C12 | 111.3 (5) | C26—C25—C24 | 110.0 (5) |
C10—C11—H11A | 109.4 | C26—C25—H25A | 109.7 |
C12—C11—H11A | 109.4 | C24—C25—H25A | 109.7 |
C10—C11—H11B | 109.4 | C26—C25—H25B | 109.7 |
C12—C11—H11B | 109.4 | C24—C25—H25B | 109.7 |
H11A—C11—H11B | 108.0 | H25A—C25—H25B | 108.2 |
C11—C12—C13 | 111.3 (5) | C27—C26—C25 | 110.1 (5) |
C11—C12—H12A | 109.4 | C27—C26—H26A | 109.6 |
C13—C12—H12A | 109.4 | C25—C26—H26A | 109.6 |
C11—C12—H12B | 109.4 | C27—C26—H26B | 109.6 |
C13—C12—H12B | 109.4 | C25—C26—H26B | 109.6 |
H12A—C12—H12B | 108.0 | H26A—C26—H26B | 108.2 |
C14—C13—C12 | 111.9 (5) | C26—C27—C28 | 110.6 (5) |
C14—C13—H13A | 109.2 | C26—C27—H27A | 109.5 |
C12—C13—H13A | 109.2 | C28—C27—H27A | 109.5 |
C14—C13—H13B | 109.2 | C26—C27—H27B | 109.5 |
C12—C13—H13B | 109.2 | C28—C27—H27B | 109.5 |
H13A—C13—H13B | 107.9 | H27A—C27—H27B | 108.1 |
C13—C14—C9 | 112.3 (5) | C27—C28—C23 | 111.2 (5) |
C13—C14—H14A | 109.1 | C27—C28—H28A | 109.4 |
C9—C14—H14A | 109.1 | C23—C28—H28A | 109.4 |
C13—C14—H14B | 109.1 | C27—C28—H28B | 109.4 |
C9—C14—H14B | 109.1 | C23—C28—H28B | 109.4 |
H14A—C14—H14B | 107.9 | H28A—C28—H28B | 108.0 |
C8—N1—C6 | 125.6 (5) | C22—N2—C20 | 124.2 (5) |
C8—N1—C7 | 118.1 (5) | C22—N2—C21 | 119.2 (5) |
C6—N1—C7 | 116.1 (4) | C20—N2—C21 | 116.2 (4) |
C6—C1—C2—C3 | −3.5 (8) | C20—C15—C16—C17 | 0.3 (9) |
I1—C1—C2—C3 | 176.4 (4) | I2—C15—C16—C17 | −179.2 (5) |
C1—C2—C3—C4 | 1.2 (9) | C15—C16—C17—C18 | 0.5 (9) |
C2—C3—C4—C5 | 1.0 (9) | C16—C17—C18—C19 | −1.2 (9) |
C2—C3—C4—Br1 | −177.2 (4) | C16—C17—C18—Br2 | −177.9 (4) |
C3—C4—C5—C6 | −0.9 (9) | C17—C18—C19—C20 | 1.1 (9) |
Br1—C4—C5—C6 | 177.3 (4) | Br2—C18—C19—C20 | 177.9 (4) |
C4—C5—C6—C1 | −1.4 (8) | C18—C19—C20—C15 | −0.3 (9) |
C4—C5—C6—N1 | −174.1 (5) | C18—C19—C20—N2 | −176.0 (5) |
C2—C1—C6—C5 | 3.5 (8) | C16—C15—C20—C19 | −0.4 (9) |
I1—C1—C6—C5 | −176.3 (4) | I2—C15—C20—C19 | 179.1 (4) |
C2—C1—C6—N1 | 176.1 (5) | C16—C15—C20—N2 | 175.2 (5) |
I1—C1—C6—N1 | −3.8 (7) | I2—C15—C20—N2 | −5.3 (7) |
O1—C8—C9—C10 | −32.7 (7) | O2—C22—C23—C24 | −65.6 (7) |
N1—C8—C9—C10 | 151.2 (5) | N2—C22—C23—C24 | 115.4 (6) |
O1—C8—C9—C14 | 88.3 (6) | O2—C22—C23—C28 | 56.2 (7) |
N1—C8—C9—C14 | −87.9 (6) | N2—C22—C23—C28 | −122.8 (5) |
C8—C9—C10—C11 | 175.8 (5) | C22—C23—C24—C25 | 172.2 (5) |
C14—C9—C10—C11 | 54.8 (6) | C28—C23—C24—C25 | 52.6 (7) |
C9—C10—C11—C12 | −55.9 (6) | C23—C24—C25—C26 | −55.7 (7) |
C10—C11—C12—C13 | 54.6 (7) | C24—C25—C26—C27 | 59.0 (7) |
C11—C12—C13—C14 | −54.5 (7) | C25—C26—C27—C28 | −59.9 (7) |
C12—C13—C14—C9 | 55.0 (7) | C26—C27—C28—C23 | 56.3 (7) |
C8—C9—C14—C13 | −176.2 (5) | C22—C23—C28—C27 | −172.7 (5) |
C10—C9—C14—C13 | −54.3 (6) | C24—C23—C28—C27 | −52.5 (7) |
O1—C8—N1—C6 | 177.6 (5) | O2—C22—N2—C20 | 172.7 (5) |
C9—C8—N1—C6 | −6.2 (8) | C23—C22—N2—C20 | −8.3 (8) |
O1—C8—N1—C7 | 3.4 (8) | O2—C22—N2—C21 | 0.1 (8) |
C9—C8—N1—C7 | 179.6 (5) | C23—C22—N2—C21 | 179.2 (5) |
C5—C6—N1—C8 | −81.5 (7) | C19—C20—N2—C22 | −80.2 (7) |
C1—C6—N1—C8 | 106.0 (7) | C15—C20—N2—C22 | 104.1 (7) |
C5—C6—N1—C7 | 92.7 (7) | C19—C20—N2—C21 | 92.6 (7) |
C1—C6—N1—C7 | −79.8 (7) | C15—C20—N2—C21 | −83.1 (7) |