Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805038936/wn6393sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805038936/wn6393Isup2.hkl |
CCDC reference: 294134
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.
C22H26FNO2 | Dx = 1.260 Mg m−3 |
Mr = 355.44 | Melting point = 405–406 K |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3031 (16) Å | Cell parameters from 2854 reflections |
b = 10.7991 (17) Å | θ = 2.2–25.5° |
c = 17.207 (3) Å | µ = 0.09 mm−1 |
β = 101.942 (3)° | T = 294 K |
V = 1873.1 (5) Å3 | Prism, colorless |
Z = 4 | 0.28 × 0.26 × 0.24 mm |
F(000) = 760 |
Bruker SMART CCD-1000 area-detector diffractometer | 3825 independent reflections |
Radiation source: fine-focus sealed tube | 2433 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 26.4°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −12→8 |
Tmin = 0.972, Tmax = 0.979 | k = −13→13 |
10342 measured reflections | l = −18→21 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.122 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0531P)2 + 0.3765P] where P = (Fo2 + 2Fc2)/3 |
3825 reflections | (Δ/σ)max < 0.001 |
256 parameters | Δρmax = 0.14 e Å−3 |
16 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. 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) | |
F1 | 0.57396 (13) | 0.66871 (14) | −0.00416 (9) | 0.0848 (5) | |
O1 | 1.17017 (15) | 0.67276 (13) | 0.25811 (8) | 0.0612 (4) | |
O2 | 0.99669 (14) | 0.15201 (12) | 0.11810 (8) | 0.0523 (4) | |
N1 | 1.00375 (15) | 0.26234 (13) | 0.23136 (8) | 0.0377 (4) | |
C1 | 1.14219 (18) | 0.57711 (18) | 0.28953 (11) | 0.0420 (5) | |
C2 | 1.1630 (2) | 0.56718 (18) | 0.37827 (11) | 0.0470 (5) | |
H2A | 1.0848 | 0.5986 | 0.3948 | 0.056* | |
H2B | 1.2372 | 0.6195 | 0.4020 | 0.056* | |
C3 | 1.19007 (18) | 0.43566 (17) | 0.41008 (10) | 0.0411 (5) | |
C4 | 1.3242 (2) | 0.3888 (2) | 0.39746 (13) | 0.0558 (6) | |
H4A | 1.3931 | 0.4436 | 0.4233 | 0.084* | |
H4B | 1.3236 | 0.3861 | 0.3416 | 0.084* | |
H4C | 1.3401 | 0.3072 | 0.4195 | 0.084* | |
C5 | 1.1906 (2) | 0.4313 (2) | 0.49880 (11) | 0.0576 (6) | |
H5A | 1.2657 | 0.4764 | 0.5274 | 0.086* | |
H5B | 1.1960 | 0.3467 | 0.5164 | 0.086* | |
H5C | 1.1105 | 0.4679 | 0.5084 | 0.086* | |
C6 | 1.07835 (19) | 0.35284 (17) | 0.36586 (10) | 0.0420 (5) | |
H6A | 1.0997 | 0.2672 | 0.3800 | 0.050* | |
H6B | 0.9970 | 0.3732 | 0.3830 | 0.050* | |
C7 | 1.05543 (16) | 0.36602 (16) | 0.27682 (10) | 0.0346 (4) | |
C8 | 1.08544 (17) | 0.47062 (16) | 0.24154 (10) | 0.0359 (4) | |
C9 | 1.06991 (17) | 0.47663 (17) | 0.15201 (10) | 0.0371 (4) | |
H9 | 1.1372 | 0.5342 | 0.1407 | 0.045* | |
C10 | 0.93514 (18) | 0.52485 (17) | 0.10933 (10) | 0.0363 (4) | |
C11 | 0.90444 (19) | 0.64914 (18) | 0.11584 (11) | 0.0448 (5) | |
H11 | 0.9664 | 0.7011 | 0.1467 | 0.054* | |
C12 | 0.7836 (2) | 0.6976 (2) | 0.07736 (12) | 0.0525 (5) | |
H12 | 0.7647 | 0.7811 | 0.0818 | 0.063* | |
C13 | 0.6935 (2) | 0.6207 (2) | 0.03308 (13) | 0.0540 (6) | |
C14 | 0.7180 (2) | 0.4984 (2) | 0.02456 (13) | 0.0598 (6) | |
H14 | 0.6545 | 0.4477 | −0.0062 | 0.072* | |
C15 | 0.8398 (2) | 0.45076 (19) | 0.06272 (12) | 0.0506 (5) | |
H15 | 0.8577 | 0.3673 | 0.0569 | 0.061* | |
C16 | 1.10433 (19) | 0.34855 (17) | 0.12555 (11) | 0.0423 (5) | |
H16A | 1.0853 | 0.3458 | 0.0680 | 0.051* | |
H16B | 1.1987 | 0.3347 | 0.1439 | 0.051* | |
C17 | 1.03002 (18) | 0.24621 (18) | 0.15591 (10) | 0.0400 (4) | |
C18 | 0.93609 (19) | 0.16177 (17) | 0.26654 (11) | 0.0439 (5) | |
H18 | 0.9204 | 0.1930 | 0.3173 | 0.053* | |
C19 | 0.7998 (2) | 0.1231 (2) | 0.21670 (13) | 0.0589 (6) | |
H19A | 0.7876 | 0.1560 | 0.1639 | 0.071* | 0.590 (13) |
H19B | 0.7295 | 0.1527 | 0.2408 | 0.071* | 0.590 (13) |
H19C | 0.7947 | 0.1412 | 0.1615 | 0.071* | 0.410 (13) |
H19D | 0.7300 | 0.1667 | 0.2344 | 0.071* | 0.410 (13) |
C20 | 0.8099 (8) | −0.0188 (6) | 0.2107 (4) | 0.087 (3) | 0.590 (13) |
H20A | 0.8358 | −0.0422 | 0.1617 | 0.104* | 0.590 (13) |
H20B | 0.7255 | −0.0574 | 0.2123 | 0.104* | 0.590 (13) |
C21 | 0.9178 (6) | −0.0585 (5) | 0.2839 (4) | 0.070 (2) | 0.590 (13) |
H21A | 0.8833 | −0.0594 | 0.3323 | 0.084* | 0.590 (13) |
H21B | 0.9547 | −0.1391 | 0.2761 | 0.084* | 0.590 (13) |
C20' | 0.7850 (7) | −0.0106 (8) | 0.2383 (7) | 0.068 (3) | 0.410 (13) |
H20C | 0.7206 | −0.0530 | 0.1979 | 0.081* | 0.410 (13) |
H20D | 0.7588 | −0.0182 | 0.2891 | 0.081* | 0.410 (13) |
C21' | 0.9247 (7) | −0.0610 (6) | 0.2424 (9) | 0.081 (3) | 0.410 (13) |
H21C | 0.9405 | −0.0764 | 0.1896 | 0.097* | 0.410 (13) |
H21D | 0.9382 | −0.1374 | 0.2727 | 0.097* | 0.410 (13) |
C22 | 1.0178 (2) | 0.04311 (19) | 0.28486 (14) | 0.0616 (6) | |
H22A | 1.0778 | 0.0486 | 0.3355 | 0.074* | 0.590 (13) |
H22B | 1.0673 | 0.0266 | 0.2445 | 0.074* | 0.590 (13) |
H22C | 1.0486 | 0.0336 | 0.3411 | 0.074* | 0.410 (13) |
H22D | 1.0932 | 0.0459 | 0.2602 | 0.074* | 0.410 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
F1 | 0.0491 (8) | 0.0955 (11) | 0.1000 (11) | 0.0159 (7) | −0.0074 (7) | 0.0155 (9) |
O1 | 0.0763 (11) | 0.0435 (8) | 0.0551 (9) | −0.0179 (8) | −0.0066 (8) | 0.0085 (7) |
O2 | 0.0688 (9) | 0.0455 (8) | 0.0427 (8) | 0.0002 (7) | 0.0119 (7) | −0.0111 (7) |
N1 | 0.0452 (9) | 0.0369 (9) | 0.0309 (8) | −0.0056 (7) | 0.0073 (7) | −0.0021 (7) |
C1 | 0.0401 (11) | 0.0375 (10) | 0.0445 (11) | −0.0011 (9) | 0.0000 (8) | 0.0023 (9) |
C2 | 0.0538 (12) | 0.0421 (11) | 0.0412 (11) | −0.0045 (9) | 0.0012 (9) | −0.0065 (9) |
C3 | 0.0446 (11) | 0.0435 (11) | 0.0324 (10) | −0.0031 (9) | 0.0014 (8) | −0.0026 (8) |
C4 | 0.0493 (12) | 0.0623 (14) | 0.0528 (13) | 0.0034 (11) | 0.0038 (10) | 0.0027 (11) |
C5 | 0.0676 (14) | 0.0641 (14) | 0.0366 (11) | −0.0022 (12) | 0.0002 (10) | −0.0045 (10) |
C6 | 0.0484 (11) | 0.0442 (11) | 0.0322 (10) | −0.0057 (9) | 0.0056 (8) | 0.0006 (8) |
C7 | 0.0338 (9) | 0.0377 (10) | 0.0308 (9) | −0.0015 (8) | 0.0034 (7) | −0.0023 (8) |
C8 | 0.0357 (10) | 0.0369 (10) | 0.0333 (9) | −0.0009 (8) | 0.0031 (7) | 0.0012 (8) |
C9 | 0.0382 (10) | 0.0382 (10) | 0.0351 (10) | −0.0029 (8) | 0.0078 (8) | 0.0045 (8) |
C10 | 0.0421 (10) | 0.0391 (10) | 0.0285 (9) | −0.0025 (8) | 0.0087 (8) | 0.0038 (8) |
C11 | 0.0469 (11) | 0.0431 (11) | 0.0428 (11) | −0.0012 (9) | 0.0056 (9) | −0.0013 (9) |
C12 | 0.0566 (13) | 0.0476 (12) | 0.0534 (13) | 0.0104 (10) | 0.0117 (11) | 0.0032 (10) |
C13 | 0.0393 (11) | 0.0673 (15) | 0.0530 (13) | 0.0072 (11) | 0.0039 (10) | 0.0114 (11) |
C14 | 0.0529 (14) | 0.0611 (15) | 0.0572 (14) | −0.0091 (11) | −0.0076 (11) | 0.0009 (11) |
C15 | 0.0547 (13) | 0.0430 (11) | 0.0488 (12) | −0.0024 (10) | −0.0014 (10) | 0.0006 (9) |
C16 | 0.0441 (11) | 0.0473 (12) | 0.0370 (10) | 0.0054 (9) | 0.0115 (8) | 0.0041 (9) |
C17 | 0.0442 (11) | 0.0410 (11) | 0.0341 (10) | 0.0070 (9) | 0.0064 (8) | −0.0009 (9) |
C18 | 0.0519 (12) | 0.0440 (11) | 0.0363 (10) | −0.0135 (9) | 0.0104 (9) | −0.0040 (9) |
C19 | 0.0491 (12) | 0.0772 (16) | 0.0506 (13) | −0.0163 (12) | 0.0110 (10) | −0.0135 (11) |
C20 | 0.131 (7) | 0.075 (4) | 0.051 (4) | −0.065 (5) | 0.009 (3) | −0.005 (3) |
C21 | 0.100 (4) | 0.044 (3) | 0.078 (4) | −0.012 (2) | 0.045 (3) | −0.008 (3) |
C20' | 0.075 (5) | 0.078 (5) | 0.053 (6) | −0.037 (4) | 0.016 (4) | −0.013 (4) |
C21' | 0.078 (5) | 0.054 (4) | 0.127 (8) | −0.021 (3) | 0.059 (6) | −0.031 (5) |
C22 | 0.0720 (15) | 0.0475 (13) | 0.0616 (14) | −0.0042 (11) | 0.0058 (12) | 0.0105 (11) |
F1—C13 | 1.367 (2) | C12—H12 | 0.9300 |
O1—C1 | 1.228 (2) | C13—C14 | 1.358 (3) |
O2—C17 | 1.218 (2) | C14—C15 | 1.389 (3) |
N1—C17 | 1.391 (2) | C14—H14 | 0.9300 |
N1—C7 | 1.406 (2) | C15—H15 | 0.9300 |
N1—C18 | 1.486 (2) | C16—C17 | 1.499 (3) |
C1—C8 | 1.465 (3) | C16—H16A | 0.9700 |
C1—C2 | 1.501 (3) | C16—H16B | 0.9700 |
C2—C3 | 1.527 (3) | C18—C22 | 1.530 (3) |
C2—H2A | 0.9700 | C18—C19 | 1.544 (3) |
C2—H2B | 0.9700 | C18—H18 | 0.9800 |
C3—C5 | 1.526 (3) | C19—C20' | 1.507 (8) |
C3—C4 | 1.529 (3) | C19—C20 | 1.541 (7) |
C3—C6 | 1.530 (2) | C19—H19A | 0.9601 |
C4—H4A | 0.9600 | C19—H19B | 0.9600 |
C4—H4B | 0.9600 | C19—H19C | 0.9600 |
C4—H4C | 0.9600 | C19—H19D | 0.9599 |
C5—H5A | 0.9600 | C20—C21 | 1.558 (7) |
C5—H5B | 0.9600 | C20—H20A | 0.9700 |
C5—H5C | 0.9600 | C20—H20B | 0.9700 |
C6—C7 | 1.508 (2) | C21—C22 | 1.503 (5) |
C6—H6A | 0.9700 | C21—H21A | 0.9700 |
C6—H6B | 0.9700 | C21—H21B | 0.9700 |
C7—C8 | 1.348 (2) | C20'—C21' | 1.527 (8) |
C8—C9 | 1.517 (2) | C20'—H20C | 0.9700 |
C9—C16 | 1.521 (3) | C20'—H20D | 0.9700 |
C9—C10 | 1.522 (2) | C21'—C22 | 1.558 (7) |
C9—H9 | 0.9800 | C21'—H21C | 0.9700 |
C10—C15 | 1.387 (3) | C21'—H21D | 0.9700 |
C10—C11 | 1.389 (3) | C22—H22A | 0.9600 |
C11—C12 | 1.386 (3) | C22—H22B | 0.9600 |
C11—H11 | 0.9300 | C22—H22C | 0.9600 |
C12—C13 | 1.356 (3) | C22—H22D | 0.9601 |
C17—N1—C7 | 119.65 (15) | N1—C17—C16 | 116.43 (16) |
C17—N1—C18 | 119.15 (14) | N1—C18—C22 | 114.32 (16) |
C7—N1—C18 | 120.74 (14) | N1—C18—C19 | 114.90 (16) |
O1—C1—C8 | 120.99 (17) | C22—C18—C19 | 106.65 (16) |
O1—C1—C2 | 120.72 (17) | N1—C18—H18 | 106.8 |
C8—C1—C2 | 118.28 (16) | C22—C18—H18 | 106.8 |
C1—C2—C3 | 114.09 (15) | C19—C18—H18 | 106.8 |
C1—C2—H2A | 108.7 | C20'—C19—C20 | 22.3 (4) |
C3—C2—H2A | 108.7 | C20'—C19—C18 | 104.4 (4) |
C1—C2—H2B | 108.7 | C20—C19—C18 | 103.9 (3) |
C3—C2—H2B | 108.7 | C20'—C19—H19A | 126.0 |
H2A—C2—H2B | 107.6 | C20—C19—H19A | 107.6 |
C5—C3—C2 | 110.50 (16) | C18—C19—H19A | 110.6 |
C5—C3—C4 | 108.38 (16) | C20'—C19—H19B | 95.1 |
C2—C3—C4 | 111.13 (17) | C20—C19—H19B | 115.3 |
C5—C3—C6 | 109.02 (16) | C18—C19—H19B | 110.5 |
C2—C3—C6 | 107.63 (15) | H19A—C19—H19B | 108.9 |
C4—C3—C6 | 110.17 (16) | C20'—C19—H19C | 116.9 |
C3—C4—H4A | 109.5 | C20—C19—H19C | 97.3 |
C3—C4—H4B | 109.5 | C18—C19—H19C | 110.5 |
H4A—C4—H4B | 109.5 | H19A—C19—H19C | 10.9 |
C3—C4—H4C | 109.5 | H19B—C19—H19C | 117.9 |
H4A—C4—H4C | 109.5 | C20'—C19—H19D | 105.8 |
H4B—C4—H4C | 109.5 | C20—C19—H19D | 125.1 |
C3—C5—H5A | 109.5 | C18—C19—H19D | 110.2 |
C3—C5—H5B | 109.5 | H19A—C19—H19D | 99.2 |
H5A—C5—H5B | 109.5 | H19B—C19—H19D | 11.3 |
C3—C5—H5C | 109.5 | H19C—C19—H19D | 108.8 |
H5A—C5—H5C | 109.5 | C19—C20—C21 | 105.5 (4) |
H5B—C5—H5C | 109.5 | C19—C20—H20A | 110.6 |
C7—C6—C3 | 113.18 (15) | C21—C20—H20A | 110.6 |
C7—C6—H6A | 108.9 | C19—C20—H20B | 110.6 |
C3—C6—H6A | 108.9 | C21—C20—H20B | 110.6 |
C7—C6—H6B | 108.9 | H20A—C20—H20B | 108.8 |
C3—C6—H6B | 108.9 | C22—C21—C20 | 100.4 (4) |
H6A—C6—H6B | 107.8 | C22—C21—H21A | 111.7 |
C8—C7—N1 | 120.82 (15) | C20—C21—H21A | 111.7 |
C8—C7—C6 | 122.30 (16) | C22—C21—H21B | 111.7 |
N1—C7—C6 | 116.86 (15) | C20—C21—H21B | 111.7 |
C7—C8—C1 | 120.38 (16) | H21A—C21—H21B | 109.5 |
C7—C8—C9 | 120.49 (16) | C19—C20'—C21' | 102.2 (6) |
C1—C8—C9 | 119.00 (16) | C19—C20'—H20C | 111.3 |
C8—C9—C16 | 106.44 (14) | C21'—C20'—H20C | 111.3 |
C8—C9—C10 | 113.49 (14) | C19—C20'—H20D | 111.3 |
C16—C9—C10 | 114.37 (15) | C21'—C20'—H20D | 111.3 |
C8—C9—H9 | 107.4 | H20C—C20'—H20D | 109.2 |
C16—C9—H9 | 107.4 | C20'—C21'—C22 | 104.3 (6) |
C10—C9—H9 | 107.4 | C20'—C21'—H21C | 110.9 |
C15—C10—C11 | 117.27 (18) | C22—C21'—H21C | 110.9 |
C15—C10—C9 | 123.25 (17) | C20'—C21'—H21D | 110.9 |
C11—C10—C9 | 119.47 (16) | C22—C21'—H21D | 110.9 |
C12—C11—C10 | 121.54 (19) | H21C—C21'—H21D | 108.9 |
C12—C11—H11 | 119.2 | C21—C22—C18 | 105.2 (3) |
C10—C11—H11 | 119.2 | C21—C22—C21' | 27.6 (4) |
C13—C12—C11 | 118.7 (2) | C18—C22—C21' | 104.4 (3) |
C13—C12—H12 | 120.6 | C21—C22—H22A | 111.5 |
C11—C12—H12 | 120.6 | C18—C22—H22A | 111.0 |
C12—C13—C14 | 122.3 (2) | C21'—C22—H22A | 133.5 |
C12—C13—F1 | 118.5 (2) | C21—C22—H22B | 108.8 |
C14—C13—F1 | 119.2 (2) | C18—C22—H22B | 111.0 |
C13—C14—C15 | 118.6 (2) | C21'—C22—H22B | 84.0 |
C13—C14—H14 | 120.7 | H22A—C22—H22B | 109.2 |
C15—C14—H14 | 120.7 | C21—C22—H22C | 90.9 |
C10—C15—C14 | 121.5 (2) | C18—C22—H22C | 110.5 |
C10—C15—H15 | 119.3 | C21'—C22—H22C | 116.0 |
C14—C15—H15 | 119.3 | H22A—C22—H22C | 22.4 |
C17—C16—C9 | 113.50 (15) | H22B—C22—H22C | 126.6 |
C17—C16—H16A | 108.9 | C21—C22—H22D | 129.3 |
C9—C16—H16A | 108.9 | C18—C22—H22D | 110.1 |
C17—C16—H16B | 108.9 | C21'—C22—H22D | 106.9 |
C9—C16—H16B | 108.9 | H22A—C22—H22D | 88.3 |
H16A—C16—H16B | 107.7 | H22B—C22—H22D | 23.8 |
O2—C17—N1 | 121.03 (17) | H22C—C22—H22D | 108.7 |
O2—C17—C16 | 122.52 (17) | ||
O1—C1—C2—C3 | −151.56 (19) | C12—C13—C14—C15 | 0.0 (3) |
C8—C1—C2—C3 | 29.5 (3) | F1—C13—C14—C15 | −179.98 (18) |
C1—C2—C3—C5 | −172.05 (17) | C11—C10—C15—C14 | −0.5 (3) |
C1—C2—C3—C4 | 67.6 (2) | C9—C10—C15—C14 | −179.84 (18) |
C1—C2—C3—C6 | −53.1 (2) | C13—C14—C15—C10 | 0.5 (3) |
C5—C3—C6—C7 | 171.01 (16) | C8—C9—C16—C17 | 51.8 (2) |
C2—C3—C6—C7 | 51.1 (2) | C10—C9—C16—C17 | −74.38 (19) |
C4—C3—C6—C7 | −70.2 (2) | C7—N1—C17—O2 | 173.39 (17) |
C17—N1—C7—C8 | 25.1 (2) | C18—N1—C17—O2 | 1.1 (3) |
C18—N1—C7—C8 | −162.74 (16) | C7—N1—C17—C16 | −4.8 (2) |
C17—N1—C7—C6 | −153.40 (16) | C18—N1—C17—C16 | −177.12 (15) |
C18—N1—C7—C6 | 18.8 (2) | C9—C16—C17—O2 | 146.89 (18) |
C3—C6—C7—C8 | −26.5 (2) | C9—C16—C17—N1 | −34.9 (2) |
C3—C6—C7—N1 | 151.93 (16) | C17—N1—C18—C22 | 66.4 (2) |
N1—C7—C8—C1 | −178.54 (16) | C7—N1—C18—C22 | −105.78 (19) |
C6—C7—C8—C1 | −0.1 (3) | C17—N1—C18—C19 | −57.4 (2) |
N1—C7—C8—C9 | −2.8 (3) | C7—N1—C18—C19 | 130.41 (18) |
C6—C7—C8—C9 | 175.62 (16) | N1—C18—C19—C20' | 152.1 (4) |
O1—C1—C8—C7 | 179.86 (18) | C22—C18—C19—C20' | 24.3 (5) |
C2—C1—C8—C7 | −1.2 (3) | N1—C18—C19—C20 | 129.1 (4) |
O1—C1—C8—C9 | 4.0 (3) | C22—C18—C19—C20 | 1.3 (4) |
C2—C1—C8—C9 | −177.04 (16) | C20'—C19—C20—C21 | −70.0 (11) |
C7—C8—C9—C16 | −34.5 (2) | C18—C19—C20—C21 | 24.2 (8) |
C1—C8—C9—C16 | 141.32 (16) | C19—C20—C21—C22 | −40.7 (9) |
C7—C8—C9—C10 | 92.2 (2) | C20—C19—C20'—C21' | 51.2 (11) |
C1—C8—C9—C10 | −92.00 (19) | C18—C19—C20'—C21' | −40.2 (10) |
C8—C9—C10—C15 | −109.6 (2) | C19—C20'—C21'—C22 | 41.2 (12) |
C16—C9—C10—C15 | 12.8 (2) | C20—C21—C22—C18 | 41.1 (7) |
C8—C9—C10—C11 | 71.1 (2) | C20—C21—C22—C21' | −50.9 (8) |
C16—C9—C10—C11 | −166.51 (16) | N1—C18—C22—C21 | −155.4 (3) |
C15—C10—C11—C12 | 0.0 (3) | C19—C18—C22—C21 | −27.3 (4) |
C9—C10—C11—C12 | 179.29 (17) | N1—C18—C22—C21' | −126.9 (5) |
C10—C11—C12—C13 | 0.6 (3) | C19—C18—C22—C21' | 1.3 (6) |
C11—C12—C13—C14 | −0.6 (3) | C20'—C21'—C22—C21 | 69.4 (9) |
C11—C12—C13—F1 | 179.42 (17) | C20'—C21'—C22—C18 | −26.0 (11) |