Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806000195/ya6275sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806000195/ya6275Isup2.hkl |
CCDC reference: 298584
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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, 2002); software used to prepare material for publication: SHELXL97.
C30H26NO4P | Z = 2 |
Mr = 495.49 | F(000) = 520 |
Triclinic, P1 | Dx = 1.312 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.9346 (10) Å | Cell parameters from 1645 reflections |
b = 10.1613 (12) Å | θ = 2.3–24.2° |
c = 14.8002 (16) Å | µ = 0.15 mm−1 |
α = 71.628 (2)° | T = 298 K |
β = 89.328 (2)° | Block, colourless |
γ = 79.940 (2)° | 0.19 × 0.14 × 0.12 mm |
V = 1254.2 (2) Å3 |
Bruker APEX area-detector diffractometer | 4459 independent reflections |
Radiation source: fine-focus sealed tube | 3371 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
φ and ω scans | θmax = 25.2°, θmin = 2.1° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→10 |
Tmin = 0.970, Tmax = 0.982 | k = −12→9 |
6745 measured reflections | l = −17→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)] = 0.072 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.159 | H-atom parameters constrained |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0518P)2 + 0.6569P] where P = (Fo2 + 2Fc2)/3 |
4459 reflections | (Δ/σ)max < 0.001 |
326 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.28 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 | ||
P1 | 0.10334 (9) | 0.41810 (9) | 0.79589 (6) | 0.0334 (2) | |
O1 | 0.7209 (3) | −0.0431 (3) | 0.5758 (2) | 0.0665 (8) | |
O2 | 0.5795 (3) | −0.0525 (3) | 0.70809 (17) | 0.0597 (7) | |
O3 | 0.0793 (3) | 0.6766 (2) | 0.49580 (15) | 0.0447 (6) | |
O4 | −0.0170 (3) | 0.6317 (2) | 0.63975 (16) | 0.0486 (6) | |
N1 | 0.1862 (3) | 0.3779 (3) | 0.71138 (18) | 0.0359 (6) | |
C1 | 0.7018 (5) | −0.1257 (4) | 0.6699 (3) | 0.0676 (12) | |
H1A | 0.7947 | −0.1427 | 0.7083 | 0.081* | |
H1B | 0.6794 | −0.2159 | 0.6704 | 0.081* | |
C2 | 0.5321 (4) | 0.0746 (4) | 0.6382 (2) | 0.0398 (8) | |
C3 | 0.6171 (4) | 0.0797 (4) | 0.5598 (3) | 0.0465 (9) | |
C4 | 0.5949 (4) | 0.1939 (4) | 0.4802 (3) | 0.0593 (11) | |
H4 | 0.6530 | 0.1972 | 0.4272 | 0.071* | |
C5 | 0.4812 (4) | 0.3056 (4) | 0.4814 (2) | 0.0503 (9) | |
H5 | 0.4631 | 0.3851 | 0.4275 | 0.060* | |
C6 | 0.3931 (3) | 0.3032 (3) | 0.5602 (2) | 0.0351 (7) | |
C7 | 0.4202 (3) | 0.1834 (3) | 0.6419 (2) | 0.0380 (8) | |
H7 | 0.3647 | 0.1784 | 0.6961 | 0.046* | |
C8 | 0.2770 (3) | 0.4268 (3) | 0.5516 (2) | 0.0356 (7) | |
H8 | 0.2646 | 0.4935 | 0.4912 | 0.043* | |
C9 | 0.1844 (3) | 0.4611 (3) | 0.6166 (2) | 0.0326 (7) | |
C10 | 0.0725 (3) | 0.5965 (3) | 0.5861 (2) | 0.0366 (8) | |
C11 | −0.0211 (4) | 0.8127 (4) | 0.4690 (3) | 0.0545 (10) | |
H11A | 0.0073 | 0.8689 | 0.5060 | 0.065* | |
H11B | −0.1252 | 0.8000 | 0.4820 | 0.065* | |
C12 | −0.0091 (5) | 0.8860 (4) | 0.3659 (3) | 0.0693 (12) | |
H12A | 0.0955 | 0.8916 | 0.3526 | 0.104* | |
H12B | −0.0684 | 0.9794 | 0.3489 | 0.104* | |
H12C | −0.0466 | 0.8345 | 0.3294 | 0.104* | |
C13 | 0.1884 (3) | 0.2804 (4) | 0.9032 (2) | 0.0367 (8) | |
C14 | 0.1697 (5) | 0.1429 (4) | 0.9172 (3) | 0.0662 (12) | |
H14 | 0.1129 | 0.1233 | 0.8723 | 0.079* | |
C15 | 0.2338 (6) | 0.0350 (5) | 0.9964 (3) | 0.0827 (15) | |
H15 | 0.2199 | −0.0566 | 1.0049 | 0.099* | |
C16 | 0.3183 (5) | 0.0627 (5) | 1.0629 (3) | 0.0729 (13) | |
H16 | 0.3629 | −0.0104 | 1.1160 | 0.087* | |
C17 | 0.3366 (5) | 0.1971 (5) | 1.0512 (3) | 0.0647 (12) | |
H17 | 0.3929 | 0.2157 | 1.0968 | 0.078* | |
C18 | 0.2718 (4) | 0.3070 (4) | 0.9714 (2) | 0.0485 (9) | |
H18 | 0.2847 | 0.3986 | 0.9640 | 0.058* | |
C19 | 0.1382 (4) | 0.5797 (3) | 0.8121 (2) | 0.0372 (8) | |
C20 | 0.2768 (4) | 0.6186 (4) | 0.7826 (3) | 0.0498 (9) | |
H20 | 0.3452 | 0.5620 | 0.7565 | 0.060* | |
C21 | 0.3140 (5) | 0.7395 (5) | 0.7916 (3) | 0.0636 (11) | |
H21 | 0.4070 | 0.7644 | 0.7712 | 0.076* | |
C22 | 0.2154 (6) | 0.8232 (4) | 0.8303 (3) | 0.0689 (13) | |
H22 | 0.2417 | 0.9042 | 0.8372 | 0.083* | |
C23 | 0.0775 (6) | 0.7873 (4) | 0.8588 (3) | 0.0663 (12) | |
H23 | 0.0098 | 0.8450 | 0.8845 | 0.080* | |
C24 | 0.0380 (4) | 0.6666 (4) | 0.8499 (2) | 0.0507 (9) | |
H24 | −0.0560 | 0.6435 | 0.8693 | 0.061* | |
C25 | −0.0964 (3) | 0.4039 (3) | 0.8060 (2) | 0.0385 (8) | |
C26 | −0.1716 (4) | 0.3835 (4) | 0.7314 (3) | 0.0485 (9) | |
H26 | −0.1238 | 0.3899 | 0.6744 | 0.058* | |
C27 | −0.3162 (4) | 0.3540 (4) | 0.7411 (3) | 0.0650 (12) | |
H27 | −0.3652 | 0.3392 | 0.6909 | 0.078* | |
C28 | −0.3884 (5) | 0.3461 (5) | 0.8239 (4) | 0.0746 (14) | |
H28 | −0.4863 | 0.3258 | 0.8301 | 0.090* | |
C29 | −0.3168 (5) | 0.3680 (5) | 0.8980 (3) | 0.0699 (13) | |
H29 | −0.3670 | 0.3645 | 0.9539 | 0.084* | |
C30 | −0.1712 (4) | 0.3951 (4) | 0.8897 (3) | 0.0530 (10) | |
H30 | −0.1222 | 0.4077 | 0.9406 | 0.064* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0323 (5) | 0.0348 (5) | 0.0321 (4) | 0.0010 (4) | 0.0020 (3) | −0.0130 (4) |
O1 | 0.0580 (17) | 0.0592 (18) | 0.0711 (19) | 0.0181 (14) | 0.0140 (14) | −0.0206 (15) |
O2 | 0.0630 (17) | 0.0450 (16) | 0.0554 (16) | 0.0126 (13) | 0.0039 (13) | −0.0061 (13) |
O3 | 0.0495 (14) | 0.0367 (13) | 0.0400 (13) | 0.0054 (11) | 0.0043 (11) | −0.0083 (11) |
O4 | 0.0496 (14) | 0.0482 (15) | 0.0417 (13) | 0.0095 (12) | 0.0065 (11) | −0.0153 (12) |
N1 | 0.0389 (15) | 0.0304 (15) | 0.0362 (15) | 0.0027 (12) | 0.0027 (12) | −0.0122 (12) |
C1 | 0.058 (3) | 0.050 (2) | 0.081 (3) | 0.016 (2) | 0.003 (2) | −0.014 (2) |
C2 | 0.0364 (18) | 0.0376 (19) | 0.0446 (19) | −0.0036 (15) | −0.0002 (15) | −0.0134 (16) |
C3 | 0.0375 (19) | 0.047 (2) | 0.053 (2) | 0.0067 (16) | 0.0056 (16) | −0.0217 (19) |
C4 | 0.055 (2) | 0.066 (3) | 0.049 (2) | 0.007 (2) | 0.0192 (19) | −0.018 (2) |
C5 | 0.052 (2) | 0.047 (2) | 0.043 (2) | 0.0019 (18) | 0.0083 (17) | −0.0090 (17) |
C6 | 0.0330 (17) | 0.041 (2) | 0.0327 (17) | −0.0029 (15) | 0.0036 (13) | −0.0156 (15) |
C7 | 0.0374 (18) | 0.043 (2) | 0.0364 (18) | −0.0063 (15) | 0.0065 (14) | −0.0180 (16) |
C8 | 0.0405 (18) | 0.0336 (18) | 0.0310 (17) | −0.0012 (14) | 0.0025 (14) | −0.0110 (14) |
C9 | 0.0333 (17) | 0.0313 (17) | 0.0338 (17) | −0.0009 (14) | −0.0010 (13) | −0.0140 (14) |
C10 | 0.0363 (18) | 0.0388 (19) | 0.0344 (18) | −0.0031 (15) | 0.0013 (14) | −0.0129 (16) |
C11 | 0.060 (2) | 0.037 (2) | 0.056 (2) | 0.0094 (18) | −0.0063 (19) | −0.0104 (18) |
C12 | 0.089 (3) | 0.047 (2) | 0.054 (2) | 0.004 (2) | −0.010 (2) | 0.001 (2) |
C13 | 0.0366 (18) | 0.042 (2) | 0.0301 (17) | 0.0011 (15) | 0.0039 (14) | −0.0132 (15) |
C14 | 0.101 (3) | 0.045 (2) | 0.051 (2) | 0.001 (2) | −0.020 (2) | −0.020 (2) |
C15 | 0.134 (4) | 0.040 (2) | 0.062 (3) | 0.009 (3) | −0.020 (3) | −0.012 (2) |
C16 | 0.086 (3) | 0.062 (3) | 0.048 (2) | 0.021 (3) | −0.013 (2) | −0.004 (2) |
C17 | 0.061 (3) | 0.083 (3) | 0.042 (2) | −0.013 (2) | −0.0107 (19) | −0.009 (2) |
C18 | 0.048 (2) | 0.055 (2) | 0.039 (2) | −0.0106 (18) | −0.0002 (16) | −0.0094 (18) |
C19 | 0.0433 (19) | 0.0362 (19) | 0.0301 (17) | 0.0012 (15) | −0.0023 (14) | −0.0122 (14) |
C20 | 0.051 (2) | 0.045 (2) | 0.057 (2) | −0.0095 (18) | 0.0043 (18) | −0.0213 (19) |
C21 | 0.075 (3) | 0.061 (3) | 0.059 (3) | −0.028 (2) | −0.004 (2) | −0.018 (2) |
C22 | 0.114 (4) | 0.043 (2) | 0.054 (3) | −0.020 (3) | −0.011 (3) | −0.017 (2) |
C23 | 0.097 (3) | 0.046 (3) | 0.060 (3) | 0.006 (2) | 0.002 (2) | −0.034 (2) |
C24 | 0.056 (2) | 0.051 (2) | 0.046 (2) | 0.0021 (18) | 0.0036 (17) | −0.0225 (18) |
C25 | 0.0347 (18) | 0.0372 (19) | 0.0390 (18) | 0.0021 (15) | 0.0028 (14) | −0.0105 (15) |
C26 | 0.045 (2) | 0.051 (2) | 0.049 (2) | −0.0121 (18) | 0.0008 (16) | −0.0120 (18) |
C27 | 0.047 (2) | 0.063 (3) | 0.078 (3) | −0.014 (2) | −0.013 (2) | −0.010 (2) |
C28 | 0.037 (2) | 0.058 (3) | 0.109 (4) | −0.008 (2) | 0.005 (2) | 0.002 (3) |
C29 | 0.052 (3) | 0.071 (3) | 0.072 (3) | −0.005 (2) | 0.024 (2) | −0.005 (2) |
C30 | 0.046 (2) | 0.062 (3) | 0.048 (2) | −0.0014 (19) | 0.0095 (17) | −0.0178 (19) |
P1—N1 | 1.573 (3) | C13—C18 | 1.381 (5) |
P1—C13 | 1.820 (3) | C13—C14 | 1.386 (5) |
P1—C19 | 1.811 (3) | C14—C15 | 1.375 (5) |
P1—C25 | 1.816 (3) | C14—H14 | 0.9300 |
O1—C1 | 1.407 (5) | C15—C16 | 1.373 (6) |
O1—C3 | 1.374 (4) | C15—H15 | 0.9300 |
O2—C1 | 1.426 (4) | C16—C17 | 1.360 (6) |
O2—C2 | 1.376 (4) | C16—H16 | 0.9300 |
O3—C10 | 1.335 (4) | C17—C18 | 1.391 (5) |
O3—C11 | 1.451 (4) | C17—H17 | 0.9300 |
O4—C10 | 1.209 (3) | C18—H18 | 0.9300 |
N1—C9 | 1.389 (4) | C19—C24 | 1.385 (4) |
C1—H1A | 0.9700 | C19—C20 | 1.389 (5) |
C1—H1B | 0.9700 | C20—C21 | 1.373 (5) |
C2—C7 | 1.369 (4) | C20—H20 | 0.9300 |
C2—C3 | 1.372 (5) | C21—C22 | 1.364 (6) |
C3—C4 | 1.355 (5) | C21—H21 | 0.9300 |
C4—C5 | 1.389 (5) | C22—C23 | 1.371 (6) |
C4—H4 | 0.9300 | C22—H22 | 0.9300 |
C5—C6 | 1.396 (4) | C23—C24 | 1.378 (5) |
C5—H5 | 0.9300 | C23—H23 | 0.9300 |
C6—C7 | 1.407 (4) | C24—H24 | 0.9300 |
C6—C8 | 1.455 (4) | C25—C30 | 1.386 (4) |
C7—H7 | 0.9300 | C25—C26 | 1.387 (5) |
C8—C9 | 1.351 (4) | C26—C27 | 1.372 (5) |
C8—H8 | 0.9300 | C26—H26 | 0.9300 |
C9—C10 | 1.495 (4) | C27—C28 | 1.365 (6) |
C11—C12 | 1.485 (5) | C27—H27 | 0.9300 |
C11—H11A | 0.9700 | C28—C29 | 1.372 (6) |
C11—H11B | 0.9700 | C28—H28 | 0.9300 |
C12—H12A | 0.9600 | C29—C30 | 1.373 (5) |
C12—H12B | 0.9600 | C29—H29 | 0.9300 |
C12—H12C | 0.9600 | C30—H30 | 0.9300 |
N1—P1—C19 | 115.60 (15) | C18—C13—C14 | 118.4 (3) |
N1—P1—C25 | 116.52 (15) | C18—C13—P1 | 122.7 (3) |
C19—P1—C25 | 111.67 (15) | C14—C13—P1 | 118.9 (3) |
N1—P1—C13 | 104.93 (14) | C15—C14—C13 | 121.0 (4) |
C19—P1—C13 | 104.30 (15) | C15—C14—H14 | 119.5 |
C25—P1—C13 | 101.70 (15) | C13—C14—H14 | 119.5 |
C3—O1—C1 | 105.8 (3) | C16—C15—C14 | 120.0 (4) |
C2—O2—C1 | 105.8 (3) | C16—C15—H15 | 120.0 |
C10—O3—C11 | 115.0 (3) | C14—C15—H15 | 120.0 |
C9—N1—P1 | 127.9 (2) | C17—C16—C15 | 120.0 (4) |
O1—C1—O2 | 108.8 (3) | C17—C16—H16 | 120.0 |
O1—C1—H1A | 109.9 | C15—C16—H16 | 120.0 |
O2—C1—H1A | 109.9 | C16—C17—C18 | 120.4 (4) |
O1—C1—H1B | 109.9 | C16—C17—H17 | 119.8 |
O2—C1—H1B | 109.9 | C18—C17—H17 | 119.8 |
H1A—C1—H1B | 108.3 | C13—C18—C17 | 120.2 (4) |
C7—C2—C3 | 122.8 (3) | C13—C18—H18 | 119.9 |
C7—C2—O2 | 128.0 (3) | C17—C18—H18 | 119.9 |
C3—C2—O2 | 109.2 (3) | C24—C19—C20 | 118.3 (3) |
C4—C3—C2 | 121.7 (3) | C24—C19—P1 | 125.4 (3) |
C4—C3—O1 | 127.9 (3) | C20—C19—P1 | 116.3 (3) |
C2—C3—O1 | 110.4 (3) | C21—C20—C19 | 120.8 (4) |
C3—C4—C5 | 116.9 (3) | C21—C20—H20 | 119.6 |
C3—C4—H4 | 121.6 | C19—C20—H20 | 119.6 |
C5—C4—H4 | 121.6 | C22—C21—C20 | 120.4 (4) |
C4—C5—C6 | 122.6 (3) | C22—C21—H21 | 119.8 |
C4—C5—H5 | 118.7 | C20—C21—H21 | 119.8 |
C6—C5—H5 | 118.7 | C21—C22—C23 | 119.7 (4) |
C5—C6—C7 | 119.0 (3) | C21—C22—H22 | 120.1 |
C5—C6—C8 | 116.9 (3) | C23—C22—H22 | 120.1 |
C7—C6—C8 | 124.1 (3) | C22—C23—C24 | 120.7 (4) |
C2—C7—C6 | 117.0 (3) | C22—C23—H23 | 119.7 |
C2—C7—H7 | 121.5 | C24—C23—H23 | 119.7 |
C6—C7—H7 | 121.5 | C23—C24—C19 | 120.2 (4) |
C9—C8—C6 | 130.8 (3) | C23—C24—H24 | 119.9 |
C9—C8—H8 | 114.6 | C19—C24—H24 | 119.9 |
C6—C8—H8 | 114.6 | C30—C25—C26 | 118.5 (3) |
C8—C9—N1 | 124.0 (3) | C30—C25—P1 | 122.4 (3) |
C8—C9—C10 | 118.8 (3) | C26—C25—P1 | 118.7 (2) |
N1—C9—C10 | 117.2 (3) | C27—C26—C25 | 120.5 (4) |
O4—C10—O3 | 122.3 (3) | C27—C26—H26 | 119.8 |
O4—C10—C9 | 122.3 (3) | C25—C26—H26 | 119.8 |
O3—C10—C9 | 115.4 (3) | C28—C27—C26 | 120.3 (4) |
O3—C11—C12 | 109.1 (3) | C28—C27—H27 | 119.8 |
O3—C11—H11A | 109.9 | C26—C27—H27 | 119.8 |
C12—C11—H11A | 109.9 | C27—C28—C29 | 120.1 (4) |
O3—C11—H11B | 109.9 | C27—C28—H28 | 119.9 |
C12—C11—H11B | 109.9 | C29—C28—H28 | 119.9 |
H11A—C11—H11B | 108.3 | C28—C29—C30 | 120.0 (4) |
C11—C12—H12A | 109.5 | C28—C29—H29 | 120.0 |
C11—C12—H12B | 109.5 | C30—C29—H29 | 120.0 |
H12A—C12—H12B | 109.5 | C29—C30—C25 | 120.6 (4) |
C11—C12—H12C | 109.5 | C29—C30—H30 | 119.7 |
H12A—C12—H12C | 109.5 | C25—C30—H30 | 119.7 |
H12B—C12—H12C | 109.5 | ||
C19—P1—N1—C9 | −52.6 (3) | C19—P1—C13—C14 | 174.4 (3) |
C25—P1—N1—C9 | 81.6 (3) | C25—P1—C13—C14 | 58.2 (3) |
C13—P1—N1—C9 | −166.8 (3) | C18—C13—C14—C15 | −0.7 (6) |
C3—O1—C1—O2 | 2.8 (4) | P1—C13—C14—C15 | 179.0 (4) |
C2—O2—C1—O1 | −2.6 (4) | C13—C14—C15—C16 | −0.2 (7) |
C1—O2—C2—C7 | −178.0 (4) | C14—C15—C16—C17 | 1.0 (7) |
C1—O2—C2—C3 | 1.4 (4) | C15—C16—C17—C18 | −0.8 (7) |
C7—C2—C3—C4 | −0.3 (6) | C14—C13—C18—C17 | 0.9 (5) |
O2—C2—C3—C4 | −179.7 (3) | P1—C13—C18—C17 | −178.8 (3) |
C7—C2—C3—O1 | 179.8 (3) | C16—C17—C18—C13 | −0.1 (6) |
O2—C2—C3—O1 | 0.4 (4) | N1—P1—C19—C24 | 151.1 (3) |
C1—O1—C3—C4 | 178.1 (4) | C25—P1—C19—C24 | 14.8 (3) |
C1—O1—C3—C2 | −1.9 (4) | C13—P1—C19—C24 | −94.2 (3) |
C2—C3—C4—C5 | −0.3 (6) | N1—P1—C19—C20 | −28.1 (3) |
O1—C3—C4—C5 | 179.6 (4) | C25—P1—C19—C20 | −164.4 (2) |
C3—C4—C5—C6 | 0.4 (6) | C13—P1—C19—C20 | 86.6 (3) |
C4—C5—C6—C7 | 0.2 (5) | C24—C19—C20—C21 | 0.6 (5) |
C4—C5—C6—C8 | −179.5 (3) | P1—C19—C20—C21 | 179.8 (3) |
C3—C2—C7—C6 | 0.8 (5) | C19—C20—C21—C22 | 0.4 (6) |
O2—C2—C7—C6 | −179.9 (3) | C20—C21—C22—C23 | −1.0 (6) |
C5—C6—C7—C2 | −0.7 (5) | C21—C22—C23—C24 | 0.7 (6) |
C8—C6—C7—C2 | 178.9 (3) | C22—C23—C24—C19 | 0.2 (6) |
C5—C6—C8—C9 | −173.6 (3) | C20—C19—C24—C23 | −0.9 (5) |
C7—C6—C8—C9 | 6.7 (5) | P1—C19—C24—C23 | 179.9 (3) |
C6—C8—C9—N1 | 1.3 (5) | N1—P1—C25—C30 | 160.6 (3) |
C6—C8—C9—C10 | −178.8 (3) | C19—P1—C25—C30 | −63.5 (3) |
P1—N1—C9—C8 | 169.2 (3) | C13—P1—C25—C30 | 47.2 (3) |
P1—N1—C9—C10 | −10.6 (4) | N1—P1—C25—C26 | −11.1 (3) |
C11—O3—C10—O4 | 4.0 (5) | C19—P1—C25—C26 | 124.7 (3) |
C11—O3—C10—C9 | −175.2 (3) | C13—P1—C25—C26 | −124.6 (3) |
C8—C9—C10—O4 | 177.8 (3) | C30—C25—C26—C27 | −0.6 (5) |
N1—C9—C10—O4 | −2.4 (5) | P1—C25—C26—C27 | 171.5 (3) |
C8—C9—C10—O3 | −3.1 (4) | C25—C26—C27—C28 | 0.8 (6) |
N1—C9—C10—O3 | 176.8 (3) | C26—C27—C28—C29 | 0.1 (7) |
C10—O3—C11—C12 | −176.3 (3) | C27—C28—C29—C30 | −1.3 (7) |
N1—P1—C13—C18 | 116.0 (3) | C28—C29—C30—C25 | 1.5 (6) |
C19—P1—C13—C18 | −5.9 (3) | C26—C25—C30—C29 | −0.6 (6) |
C25—P1—C13—C18 | −122.1 (3) | P1—C25—C30—C29 | −172.3 (3) |
N1—P1—C13—C14 | −63.6 (3) |