Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806021131/gh2002sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806021131/gh2002Isup2.hkl |
CCDC reference: 613683
Data collection: CAD4/Mach3 (Enraf–Nonius, 2000); cell refinement: CAD4/Mach3; data reduction: HELENA (Spek, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: PLATON.
C23H31N2O3+·CF3SO3− | F(000) = 560 |
Mr = 532.57 | Dx = 1.407 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 11.312 (1) Å | θ = 20–35° |
b = 8.059 (1) Å | µ = 1.72 mm−1 |
c = 14.074 (1) Å | T = 293 K |
β = 101.49 (1)° | Prism, colorless |
V = 1257.3 (2) Å3 | 0.50 × 0.35 × 0.20 mm |
Z = 2 |
Enraf–Nonius CAD-4 diffractometer | 2634 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 75.0°, θmin = 3.2° |
ω/2θ scans | h = −14→13 |
Absorption correction: analytical de Meulenaer & Tompa 1965 | k = 0→10 |
Tmin = 0.480, Tmax = 0.725 | l = 0→17 |
2906 measured reflections | 3 standard reflections every 60 reflections |
2794 independent reflections | intensity decay: 1.5% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.043 | w = 1/[σ2(Fo2) + (0.082P)2 + 0.328P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.124 | (Δ/σ)max = 0.002 |
S = 0.99 | Δρmax = 0.33 e Å−3 |
2794 reflections | Δρmin = −0.34 e Å−3 |
333 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0263 (16) |
Primary atom site location: structure-invariant direct methods | Absolute structure: not refined (see text) |
Secondary atom site location: difference Fourier map |
Experimental. No Friedel related reflections were measured in the present data collection. Thus Flack test results are meaningless. |
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 | ||
O12 | 0.21910 (17) | 0.2748 (3) | 0.82739 (13) | 0.0369 (5) | |
O26 | 0.3721 (2) | 0.1585 (3) | 0.94418 (19) | 0.0478 (6) | |
O27 | 0.5594 (4) | 0.0800 (7) | 0.5116 (3) | 0.1006 (14) | |
N1 | 0.0675 (4) | 0.1236 (6) | 0.4824 (2) | 0.0748 (11) | |
N15 | 0.3358 (2) | 0.5614 (3) | 0.84133 (15) | 0.0353 (5) | |
C2 | 0.0215 (4) | 0.1758 (6) | 0.5551 (3) | 0.0699 (11) | |
H2 | −0.0621 | 0.1786 | 0.5472 | 0.084* | |
C3 | 0.0906 (3) | 0.2283 (5) | 0.6448 (2) | 0.0536 (8) | |
H3 | 0.0525 | 0.2637 | 0.6940 | 0.064* | |
C4 | 0.2131 (3) | 0.2268 (4) | 0.6589 (2) | 0.0425 (7) | |
C5 | 0.2687 (3) | 0.1713 (4) | 0.5829 (2) | 0.0471 (7) | |
C6 | 0.3950 (4) | 0.1594 (5) | 0.5900 (2) | 0.0538 (8) | |
H6 | 0.4473 | 0.1904 | 0.6468 | 0.065* | |
C7 | 0.4396 (5) | 0.1021 (7) | 0.5127 (3) | 0.0714 (12) | |
C8 | 0.3613 (7) | 0.0602 (9) | 0.4249 (3) | 0.0916 (18) | |
H8 | 0.3932 | 0.0264 | 0.3720 | 0.110* | |
C9 | 0.2418 (6) | 0.0687 (8) | 0.4170 (3) | 0.0897 (17) | |
H9 | 0.1917 | 0.0382 | 0.3589 | 0.108* | |
C10 | 0.1895 (4) | 0.1233 (5) | 0.4955 (2) | 0.0617 (10) | |
C11 | 0.2883 (2) | 0.2888 (4) | 0.75318 (18) | 0.0348 (6) | |
H11 | 0.3603 | 0.2189 | 0.7704 | 0.042* | |
C13 | 0.2935 (2) | 0.2931 (5) | 0.92227 (18) | 0.0377 (6) | |
C14 | 0.3772 (3) | 0.4427 (4) | 0.9231 (2) | 0.0378 (6) | |
H14A | 0.3831 | 0.5014 | 0.9840 | 0.045* | |
H14B | 0.4572 | 0.4032 | 0.9196 | 0.045* | |
C16 | 0.3286 (3) | 0.4716 (4) | 0.7442 (2) | 0.0370 (6) | |
H16 | 0.4106 | 0.4682 | 0.7315 | 0.044* | |
C17 | 0.2535 (3) | 0.5820 (4) | 0.6658 (2) | 0.0472 (7) | |
H17A | 0.2819 | 0.5703 | 0.6055 | 0.057* | |
H17B | 0.1694 | 0.5487 | 0.6545 | 0.057* | |
C18 | 0.2661 (4) | 0.7635 (4) | 0.7001 (2) | 0.0525 (8) | |
H18 | 0.2402 | 0.8392 | 0.6454 | 0.063* | |
C19 | 0.3977 (3) | 0.7963 (5) | 0.7481 (3) | 0.0579 (8) | |
H19A | 0.4506 | 0.7602 | 0.7056 | 0.070* | |
H19B | 0.4102 | 0.9141 | 0.7601 | 0.070* | |
C20 | 0.4269 (3) | 0.7001 (4) | 0.8444 (2) | 0.0472 (7) | |
H20A | 0.5077 | 0.6544 | 0.8537 | 0.057* | |
H20B | 0.4232 | 0.7741 | 0.8981 | 0.057* | |
C21 | 0.2153 (3) | 0.6401 (4) | 0.8470 (2) | 0.0393 (6) | |
H21A | 0.2165 | 0.6763 | 0.9129 | 0.047* | |
H21B | 0.1516 | 0.5585 | 0.8297 | 0.047* | |
C22 | 0.1895 (3) | 0.7893 (5) | 0.7779 (2) | 0.0495 (7) | |
H22 | 0.2178 | 0.8900 | 0.8145 | 0.059* | |
C23 | 0.0537 (3) | 0.8058 (6) | 0.7391 (3) | 0.0649 (10) | |
H23A | 0.0398 | 0.8928 | 0.6905 | 0.078* | |
H23B | 0.0236 | 0.7027 | 0.7077 | 0.078* | |
C24 | −0.0164 (4) | 0.8453 (8) | 0.8169 (4) | 0.0867 (16) | |
H24A | −0.0049 | 0.7582 | 0.8644 | 0.130* | |
H24B | −0.1006 | 0.8546 | 0.7884 | 0.130* | |
H24C | 0.0118 | 0.9483 | 0.8475 | 0.130* | |
C25 | 0.2069 (3) | 0.3051 (6) | 0.9916 (2) | 0.0491 (7) | |
H25A | 0.1608 | 0.2045 | 0.9887 | 0.074* | |
H25B | 0.1534 | 0.3973 | 0.9737 | 0.074* | |
H25C | 0.2517 | 0.3209 | 1.0565 | 0.074* | |
C28 | 0.6427 (5) | 0.0852 (12) | 0.6014 (4) | 0.105 (2) | |
H28A | 0.6581 | 0.1985 | 0.6210 | 0.157* | |
H28B | 0.7168 | 0.0331 | 0.5944 | 0.157* | |
H28C | 0.6096 | 0.0273 | 0.6497 | 0.157* | |
S30 | 0.31245 (7) | 0.80895 (14) | 0.13237 (5) | 0.0534 (3) | |
F35 | 0.1106 (4) | 0.9532 (7) | 0.1371 (5) | 0.158 (2) | |
F36 | 0.1449 (3) | 0.7475 (6) | 0.2302 (2) | 0.1063 (13) | |
F37 | 0.0925 (3) | 0.7108 (6) | 0.0777 (2) | 0.1042 (12) | |
O31 | 0.3725 (3) | 0.9052 (8) | 0.2093 (2) | 0.1173 (19) | |
O32 | 0.3450 (4) | 0.6351 (6) | 0.1408 (3) | 0.1025 (14) | |
O33 | 0.3076 (3) | 0.8745 (4) | 0.03761 (17) | 0.0626 (7) | |
C34 | 0.1578 (3) | 0.8033 (7) | 0.1460 (3) | 0.0688 (11) | |
H521 | 0.348 (4) | 0.102 (8) | 0.970 (4) | 0.069 (16)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O12 | 0.0405 (9) | 0.0406 (11) | 0.0297 (9) | −0.0029 (8) | 0.0073 (7) | −0.0001 (8) |
O26 | 0.0478 (12) | 0.0496 (14) | 0.0463 (13) | 0.0059 (11) | 0.0102 (10) | 0.0143 (11) |
O27 | 0.111 (3) | 0.130 (4) | 0.077 (2) | −0.009 (3) | 0.056 (2) | −0.039 (2) |
N1 | 0.094 (3) | 0.076 (3) | 0.0446 (16) | −0.012 (2) | −0.0115 (16) | −0.0061 (17) |
N15 | 0.0414 (11) | 0.0332 (12) | 0.0316 (11) | −0.0031 (10) | 0.0081 (9) | −0.0043 (10) |
C2 | 0.070 (2) | 0.076 (3) | 0.053 (2) | −0.010 (2) | −0.0107 (17) | 0.003 (2) |
C3 | 0.0585 (18) | 0.056 (2) | 0.0437 (16) | −0.0059 (17) | 0.0030 (14) | −0.0042 (16) |
C4 | 0.0617 (18) | 0.0326 (14) | 0.0315 (13) | −0.0041 (14) | 0.0053 (12) | −0.0021 (12) |
C5 | 0.079 (2) | 0.0313 (15) | 0.0321 (13) | −0.0060 (15) | 0.0120 (13) | −0.0035 (12) |
C6 | 0.080 (2) | 0.0485 (19) | 0.0363 (15) | −0.0073 (18) | 0.0199 (15) | −0.0081 (14) |
C7 | 0.100 (3) | 0.070 (3) | 0.052 (2) | −0.006 (2) | 0.035 (2) | −0.016 (2) |
C8 | 0.131 (5) | 0.103 (4) | 0.046 (2) | 0.001 (4) | 0.033 (3) | −0.026 (3) |
C9 | 0.137 (5) | 0.093 (4) | 0.0362 (18) | −0.008 (4) | 0.009 (2) | −0.030 (2) |
C10 | 0.094 (3) | 0.052 (2) | 0.0355 (16) | −0.008 (2) | 0.0051 (16) | −0.0054 (15) |
C11 | 0.0445 (13) | 0.0322 (13) | 0.0286 (11) | −0.0003 (12) | 0.0095 (10) | −0.0035 (11) |
C13 | 0.0391 (12) | 0.0455 (15) | 0.0292 (11) | 0.0014 (14) | 0.0083 (9) | 0.0026 (12) |
C14 | 0.0385 (13) | 0.0432 (16) | 0.0307 (13) | 0.0028 (12) | 0.0045 (10) | −0.0017 (12) |
C16 | 0.0478 (14) | 0.0352 (15) | 0.0300 (12) | −0.0020 (12) | 0.0129 (11) | −0.0053 (11) |
C17 | 0.069 (2) | 0.0411 (16) | 0.0322 (14) | −0.0018 (15) | 0.0126 (13) | 0.0010 (13) |
C18 | 0.074 (2) | 0.0400 (19) | 0.0421 (16) | −0.0046 (15) | 0.0089 (15) | 0.0057 (13) |
C19 | 0.073 (2) | 0.0411 (17) | 0.063 (2) | −0.0148 (19) | 0.0221 (16) | 0.0011 (18) |
C20 | 0.0500 (16) | 0.0411 (17) | 0.0502 (16) | −0.0098 (14) | 0.0094 (13) | −0.0081 (14) |
C21 | 0.0446 (14) | 0.0357 (15) | 0.0375 (14) | 0.0038 (12) | 0.0076 (11) | −0.0059 (12) |
C22 | 0.0617 (17) | 0.0358 (15) | 0.0475 (16) | 0.0018 (16) | 0.0024 (13) | −0.0050 (15) |
C23 | 0.067 (2) | 0.050 (2) | 0.070 (2) | 0.010 (2) | −0.0037 (17) | 0.005 (2) |
C24 | 0.066 (2) | 0.081 (4) | 0.112 (4) | 0.026 (2) | 0.014 (2) | −0.012 (3) |
C25 | 0.0486 (14) | 0.066 (2) | 0.0364 (13) | −0.0009 (18) | 0.0164 (11) | 0.0050 (17) |
C28 | 0.082 (3) | 0.148 (6) | 0.095 (4) | 0.000 (4) | 0.044 (3) | −0.031 (4) |
S30 | 0.0501 (4) | 0.0753 (6) | 0.0377 (4) | −0.0155 (4) | 0.0159 (3) | −0.0061 (4) |
F35 | 0.143 (4) | 0.114 (3) | 0.242 (6) | 0.058 (3) | 0.102 (4) | 0.030 (4) |
F36 | 0.0935 (17) | 0.155 (4) | 0.0880 (18) | −0.036 (2) | 0.0588 (15) | −0.005 (2) |
F37 | 0.0631 (14) | 0.148 (3) | 0.097 (2) | −0.0435 (18) | 0.0043 (13) | −0.006 (2) |
O31 | 0.107 (2) | 0.198 (5) | 0.0515 (16) | −0.089 (3) | 0.0272 (16) | −0.038 (2) |
O32 | 0.116 (3) | 0.092 (3) | 0.111 (3) | 0.035 (3) | 0.051 (2) | 0.030 (3) |
O33 | 0.0776 (16) | 0.0665 (17) | 0.0467 (13) | −0.0201 (14) | 0.0200 (11) | −0.0018 (12) |
C34 | 0.0549 (18) | 0.077 (3) | 0.080 (3) | −0.011 (2) | 0.0277 (18) | −0.009 (3) |
O12—C11 | 1.429 (3) | C17—C18 | 1.538 (5) |
O12—C13 | 1.437 (3) | C17—H17A | 0.9700 |
O26—C13 | 1.398 (4) | C17—H17B | 0.9700 |
O26—H521 | 0.67 (6) | C18—C22 | 1.540 (5) |
O27—C7 | 1.370 (6) | C18—C19 | 1.530 (5) |
O27—C28 | 1.419 (7) | C18—H18 | 0.9800 |
N1—C2 | 1.306 (6) | C19—C20 | 1.539 (5) |
N1—C10 | 1.356 (6) | C19—H19A | 0.9700 |
N15—C14 | 1.498 (4) | C19—H19B | 0.9700 |
N15—C21 | 1.519 (4) | C20—H20A | 0.9700 |
N15—C20 | 1.515 (4) | C20—H20B | 0.9700 |
N15—C16 | 1.534 (3) | C21—C22 | 1.537 (5) |
C2—C3 | 1.411 (5) | C21—H21A | 0.9700 |
C2—H2 | 0.9300 | C21—H21B | 0.9700 |
C3—C4 | 1.360 (5) | C22—C23 | 1.531 (5) |
C3—H3 | 0.9300 | C22—H22 | 0.9800 |
C4—C5 | 1.418 (4) | C23—C24 | 1.509 (7) |
C4—C11 | 1.511 (4) | C23—H23A | 0.9700 |
C5—C6 | 1.415 (5) | C23—H23B | 0.9700 |
C5—C10 | 1.423 (5) | C24—H24A | 0.9600 |
C6—C7 | 1.368 (5) | C24—H24B | 0.9600 |
C6—H6 | 0.9300 | C24—H24C | 0.9600 |
C7—C8 | 1.410 (7) | C25—H25A | 0.9600 |
C8—C9 | 1.336 (9) | C25—H25B | 0.9600 |
C8—H8 | 0.9300 | C25—H25C | 0.9600 |
C9—C10 | 1.424 (6) | C28—H28A | 0.9600 |
C9—H9 | 0.9300 | C28—H28B | 0.9600 |
C11—C16 | 1.555 (4) | C28—H28C | 0.9600 |
C11—H11 | 0.9800 | S30—O31 | 1.393 (4) |
C13—C25 | 1.518 (4) | S30—O33 | 1.425 (3) |
C13—C14 | 1.531 (5) | S30—O32 | 1.447 (5) |
C14—H14A | 0.9700 | S30—C34 | 1.798 (4) |
C14—H14B | 0.9700 | F35—C34 | 1.317 (8) |
C16—C17 | 1.536 (4) | F36—C34 | 1.302 (5) |
C16—H16 | 0.9800 | F37—C34 | 1.320 (6) |
C11—O12—C13 | 111.48 (19) | C22—C18—C19 | 107.4 (3) |
C13—O26—H521 | 110 (5) | C22—C18—C17 | 108.7 (3) |
C7—O27—C28 | 118.0 (3) | C19—C18—C17 | 108.9 (3) |
C2—N1—C10 | 116.6 (3) | C22—C18—H18 | 110.6 |
C14—N15—C21 | 111.9 (2) | C19—C18—H18 | 110.6 |
C14—N15—C20 | 110.0 (2) | C17—C18—H18 | 110.6 |
C21—N15—C20 | 107.6 (2) | C20—C19—C18 | 108.7 (3) |
C14—N15—C16 | 109.6 (2) | C20—C19—H19A | 109.9 |
C21—N15—C16 | 110.7 (2) | C18—C19—H19A | 109.9 |
C20—N15—C16 | 106.8 (2) | C20—C19—H19B | 109.9 |
N1—C2—C3 | 124.1 (4) | C18—C19—H19B | 109.9 |
N1—C2—H2 | 117.9 | H19A—C19—H19B | 108.3 |
C3—C2—H2 | 117.9 | N15—C20—C19 | 108.7 (2) |
C4—C3—C2 | 119.6 (4) | N15—C20—H20A | 109.9 |
C4—C3—H3 | 120.2 | C19—C20—H20A | 109.9 |
C2—C3—H3 | 120.2 | N15—C20—H20B | 109.9 |
C3—C4—C5 | 119.0 (3) | C19—C20—H20B | 109.9 |
C3—C4—C11 | 120.3 (3) | H20A—C20—H20B | 108.3 |
C5—C4—C11 | 120.6 (3) | N15—C21—C22 | 110.7 (2) |
C6—C5—C4 | 124.2 (3) | N15—C21—H21A | 109.5 |
C6—C5—C10 | 119.7 (3) | C22—C21—H21A | 109.5 |
C4—C5—C10 | 116.1 (3) | N15—C21—H21B | 109.5 |
C7—C6—C5 | 119.6 (4) | C22—C21—H21B | 109.5 |
C7—C6—H6 | 120.2 | H21A—C21—H21B | 108.1 |
C5—C6—H6 | 120.2 | C18—C22—C23 | 115.1 (3) |
O27—C7—C6 | 125.2 (4) | C18—C22—C21 | 106.3 (3) |
O27—C7—C8 | 114.2 (4) | C23—C22—C21 | 110.1 (3) |
C6—C7—C8 | 120.7 (5) | C18—C22—H22 | 108.4 |
C9—C8—C7 | 120.7 (4) | C23—C22—H22 | 108.4 |
C9—C8—H8 | 119.7 | C21—C22—H22 | 108.4 |
C7—C8—H8 | 119.7 | C24—C23—C22 | 113.2 (3) |
C8—C9—C10 | 121.4 (4) | C24—C23—H23A | 108.9 |
C8—C9—H9 | 119.3 | C22—C23—H23A | 108.9 |
C10—C9—H9 | 119.3 | C24—C23—H23B | 108.9 |
N1—C10—C5 | 124.5 (4) | C22—C23—H23B | 108.9 |
N1—C10—C9 | 117.6 (4) | H23A—C23—H23B | 107.7 |
C5—C10—C9 | 117.8 (4) | C23—C24—H24A | 109.5 |
O12—C11—C4 | 108.7 (2) | C23—C24—H24B | 109.5 |
O12—C11—C16 | 110.2 (2) | H24A—C24—H24B | 109.5 |
C4—C11—C16 | 111.4 (2) | C23—C24—H24C | 109.5 |
O12—C11—H11 | 108.8 | H24A—C24—H24C | 109.5 |
C4—C11—H11 | 108.8 | H24B—C24—H24C | 109.5 |
C16—C11—H11 | 108.8 | C13—C25—H25A | 109.5 |
O26—C13—O12 | 110.8 (3) | C13—C25—H25B | 109.5 |
O26—C13—C25 | 111.8 (3) | H25A—C25—H25B | 109.5 |
O12—C13—C25 | 105.7 (2) | C13—C25—H25C | 109.5 |
O26—C13—C14 | 104.2 (2) | H25A—C25—H25C | 109.5 |
O12—C13—C14 | 109.5 (2) | H25B—C25—H25C | 109.5 |
C25—C13—C14 | 115.0 (3) | O27—C28—H28A | 109.5 |
N15—C14—C13 | 113.5 (2) | O27—C28—H28B | 109.5 |
N15—C14—H14A | 108.9 | H28A—C28—H28B | 109.5 |
C13—C14—H14A | 108.9 | O27—C28—H28C | 109.5 |
N15—C14—H14B | 108.9 | H28A—C28—H28C | 109.5 |
C13—C14—H14B | 108.9 | H28B—C28—H28C | 109.5 |
H14A—C14—H14B | 107.7 | O31—S30—O33 | 116.3 (2) |
N15—C16—C17 | 106.9 (2) | O31—S30—O32 | 113.5 (3) |
N15—C16—C11 | 109.9 (2) | O33—S30—O32 | 113.4 (2) |
C17—C16—C11 | 118.6 (2) | O31—S30—C34 | 105.4 (2) |
N15—C16—H16 | 107.0 | O33—S30—C34 | 104.6 (2) |
C17—C16—H16 | 107.0 | O32—S30—C34 | 101.8 (3) |
C11—C16—H16 | 107.0 | F36—C34—F35 | 106.7 (5) |
C18—C17—C16 | 108.8 (3) | F36—C34—F37 | 108.6 (4) |
C18—C17—H17A | 109.9 | F35—C34—F37 | 106.9 (5) |
C16—C17—H17A | 109.9 | F36—C34—S30 | 113.2 (3) |
C18—C17—H17B | 109.9 | F35—C34—S30 | 110.6 (4) |
C16—C17—H17B | 109.9 | F37—C34—S30 | 110.6 (3) |
H17A—C17—H17B | 108.3 | ||
C10—N1—C2—C3 | −1.0 (7) | C14—N15—C16—C17 | 164.4 (2) |
N1—C2—C3—C4 | 0.3 (7) | C21—N15—C16—C17 | 40.5 (3) |
C2—C3—C4—C5 | −0.4 (6) | C20—N15—C16—C17 | −76.4 (3) |
C2—C3—C4—C11 | 177.7 (4) | C14—N15—C16—C11 | 34.5 (3) |
C3—C4—C5—C6 | −178.0 (4) | C21—N15—C16—C11 | −89.4 (3) |
C11—C4—C5—C6 | 3.9 (5) | C20—N15—C16—C11 | 153.7 (2) |
C3—C4—C5—C10 | 1.0 (5) | O12—C11—C16—N15 | 26.3 (3) |
C11—C4—C5—C10 | −177.0 (3) | C4—C11—C16—N15 | 147.0 (2) |
C4—C5—C6—C7 | 179.1 (4) | O12—C11—C16—C17 | −97.0 (3) |
C10—C5—C6—C7 | 0.1 (6) | C4—C11—C16—C17 | 23.7 (3) |
C28—O27—C7—C6 | 13.0 (9) | N15—C16—C17—C18 | 27.0 (3) |
C28—O27—C7—C8 | −167.0 (7) | C11—C16—C17—C18 | 151.7 (3) |
C5—C6—C7—O27 | −177.8 (5) | C16—C17—C18—C22 | −75.3 (4) |
C5—C6—C7—C8 | 2.2 (8) | C16—C17—C18—C19 | 41.4 (4) |
O27—C7—C8—C9 | 177.0 (6) | C22—C18—C19—C20 | 48.2 (4) |
C6—C7—C8—C9 | −3.0 (10) | C17—C18—C19—C20 | −69.3 (4) |
C7—C8—C9—C10 | 1.4 (10) | C14—N15—C20—C19 | 167.1 (3) |
C2—N1—C10—C5 | 1.8 (7) | C21—N15—C20—C19 | −70.7 (3) |
C2—N1—C10—C9 | −179.3 (5) | C16—N15—C20—C19 | 48.3 (3) |
C6—C5—C10—N1 | 177.3 (4) | C18—C19—C20—N15 | 20.6 (4) |
C4—C5—C10—N1 | −1.8 (6) | C14—N15—C21—C22 | 166.6 (2) |
C6—C5—C10—C9 | −1.6 (6) | C20—N15—C21—C22 | 45.6 (3) |
C4—C5—C10—C9 | 179.3 (4) | C16—N15—C21—C22 | −70.7 (3) |
C8—C9—C10—N1 | −178.1 (6) | C19—C18—C22—C23 | 165.1 (3) |
C8—C9—C10—C5 | 0.9 (8) | C17—C18—C22—C23 | −77.2 (4) |
C13—O12—C11—C4 | 166.0 (3) | C19—C18—C22—C21 | −72.6 (3) |
C13—O12—C11—C16 | −71.6 (3) | C17—C18—C22—C21 | 45.1 (3) |
C3—C4—C11—O12 | 24.3 (4) | N15—C21—C22—C18 | 22.4 (3) |
C5—C4—C11—O12 | −157.6 (3) | N15—C21—C22—C23 | 147.8 (3) |
C3—C4—C11—C16 | −97.3 (3) | C18—C22—C23—C24 | −175.1 (4) |
C5—C4—C11—C16 | 80.7 (3) | C21—C22—C23—C24 | 64.7 (5) |
C11—O12—C13—O26 | −68.1 (3) | O31—S30—C34—F36 | −56.2 (5) |
C11—O12—C13—C25 | 170.7 (3) | O33—S30—C34—F36 | −179.3 (4) |
C11—O12—C13—C14 | 46.2 (3) | O32—S30—C34—F36 | 62.4 (5) |
C21—N15—C14—C13 | 63.5 (3) | O31—S30—C34—F35 | 63.4 (5) |
C20—N15—C14—C13 | −176.9 (2) | O33—S30—C34—F35 | −59.7 (5) |
C16—N15—C14—C13 | −59.8 (3) | O32—S30—C34—F35 | −177.9 (5) |
O26—C13—C14—N15 | 137.5 (2) | O31—S30—C34—F37 | −178.3 (4) |
O12—C13—C14—N15 | 19.0 (3) | O33—S30—C34—F37 | 58.6 (4) |
C25—C13—C14—N15 | −99.8 (3) | O32—S30—C34—F37 | −59.7 (5) |