Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024500/hb2085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024500/hb2085Isup2.hkl |
CCDC reference: 618204
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); 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, 2000); software used to prepare material for publication: SHELXTL.
C33H34N2O6 | F(000) = 588 |
Mr = 554.62 | Dx = 1.281 Mg m−3 |
Monoclinic, P21 | Melting point: 464 K |
Hall symbol: P 2yb | Mo Kα radiation, λ = 0.71073 Å |
a = 10.0296 (14) Å | Cell parameters from 3060 reflections |
b = 12.7262 (17) Å | θ = 2.4–26.6° |
c = 11.4028 (16) Å | µ = 0.09 mm−1 |
β = 98.942 (2)° | T = 294 K |
V = 1437.7 (3) Å3 | Block, colourless |
Z = 2 | 0.24 × 0.20 × 0.18 mm |
Bruker SMART CCD diffractometer | 3556 independent reflections |
Radiation source: fine-focus sealed tube | 2445 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ω scans | θmax = 28.3°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Bruker, 2000) | h = −13→12 |
Tmin = 0.979, Tmax = 0.984 | k = −16→16 |
8933 measured reflections | l = −15→12 |
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) = 0.102 | H-atom parameters constrained |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0455P)2 + 0.0766P] where P = (Fo2 + 2Fc2)/3 |
3556 reflections | (Δ/σ)max = 0.002 |
372 parameters | Δρmax = 0.16 e Å−3 |
1 restraint | Δρmin = −0.17 e Å−3 |
Experimental. 1H NMR (CDCl3, 300 MHz): δ 1.28 (s, 3H), 1.37 (s, 3H), 1.74–2.16 (m, 4H), 3.59–3.71(m, 4H), 4.65 (s, 1H), 4.70 (d, J = 7.6 Hz, 1H), 4.84–4.90 (m, 1H), 5.29 (s, 1H), 7.26–7.31 (m, 9 H), 7.31–7.50 (m, 6H), 8.24 (s, 1H). 13C NMR (CDCl3, 75 MHz): δ 24.44, 25.44, 25.89, 34.37, 46.32, 61.47, 64.07, 71.90, 80.39, 87.22, 112.37, 127.06, 127.81, 128.82, 143.88, 160.54, 176.63. |
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 | ||
N1 | 0.6298 (2) | 0.6121 (2) | 0.5864 (2) | 0.0442 (6) | |
N2 | 0.3632 (2) | 0.68614 (17) | 0.3465 (2) | 0.0368 (5) | |
O1 | 0.5586 (2) | 0.77254 (19) | 0.6346 (2) | 0.0607 (6) | |
O2 | 0.6986 (2) | 0.7586 (2) | 0.4043 (2) | 0.0709 (7) | |
O3 | 0.4777 (2) | 0.75649 (16) | 0.33992 (18) | 0.0502 (5) | |
O4 | 0.20297 (19) | 0.5242 (2) | 0.45595 (17) | 0.0554 (6) | |
O5 | 0.15418 (19) | 0.50188 (18) | 0.25659 (17) | 0.0499 (5) | |
O6 | 0.28832 (19) | 0.77149 (15) | 0.12066 (16) | 0.0421 (5) | |
C1 | 0.5629 (3) | 0.6137 (2) | 0.4625 (2) | 0.0371 (6) | |
C2 | 0.6275 (3) | 0.5186 (3) | 0.4080 (3) | 0.0488 (7) | |
H2A | 0.5613 | 0.4824 | 0.3510 | 0.059* | |
H2B | 0.7016 | 0.5410 | 0.3685 | 0.059* | |
C3 | 0.6778 (4) | 0.4481 (3) | 0.5122 (3) | 0.0623 (9) | |
H3A | 0.6063 | 0.4023 | 0.5302 | 0.075* | |
H3B | 0.7527 | 0.4052 | 0.4958 | 0.075* | |
C4 | 0.7220 (3) | 0.5222 (3) | 0.6129 (3) | 0.0668 (10) | |
H4A | 0.7123 | 0.4905 | 0.6885 | 0.080* | |
H4B | 0.8151 | 0.5435 | 0.6146 | 0.080* | |
C5 | 0.6240 (3) | 0.6929 (3) | 0.6598 (3) | 0.0516 (8) | |
H5 | 0.6734 | 0.6881 | 0.7357 | 0.062* | |
C6 | 0.5918 (3) | 0.7159 (3) | 0.4020 (3) | 0.0457 (7) | |
C7 | 0.4083 (2) | 0.6163 (2) | 0.4496 (2) | 0.0335 (6) | |
H7 | 0.3813 | 0.6466 | 0.5213 | 0.040* | |
C8 | 0.3303 (2) | 0.5150 (2) | 0.4177 (2) | 0.0345 (6) | |
H8 | 0.3802 | 0.4524 | 0.4497 | 0.041* | |
C9 | 0.2964 (3) | 0.5136 (2) | 0.2813 (2) | 0.0347 (6) | |
H9 | 0.3416 | 0.4547 | 0.2483 | 0.042* | |
C10 | 0.3453 (3) | 0.6188 (2) | 0.2381 (2) | 0.0342 (6) | |
H10 | 0.4328 | 0.6088 | 0.2117 | 0.041* | |
C11 | 0.2467 (3) | 0.6665 (2) | 0.1383 (2) | 0.0428 (7) | |
H11A | 0.2460 | 0.6259 | 0.0661 | 0.051* | |
H11B | 0.1564 | 0.6661 | 0.1586 | 0.051* | |
C12 | 0.1004 (3) | 0.4912 (3) | 0.3646 (3) | 0.0482 (8) | |
C13 | −0.0175 (4) | 0.5617 (6) | 0.3607 (5) | 0.121 (2) | |
H13A | −0.0605 | 0.5493 | 0.4290 | 0.181* | |
H13B | −0.0804 | 0.5480 | 0.2899 | 0.181* | |
H13C | 0.0118 | 0.6335 | 0.3606 | 0.181* | |
C14 | 0.0704 (6) | 0.3763 (4) | 0.3795 (4) | 0.0995 (17) | |
H14A | 0.1534 | 0.3373 | 0.3914 | 0.149* | |
H14B | 0.0138 | 0.3511 | 0.3095 | 0.149* | |
H14C | 0.0250 | 0.3673 | 0.4469 | 0.149* | |
C15 | 0.1964 (3) | 0.8352 (2) | 0.0397 (2) | 0.0376 (6) | |
C16 | 0.2706 (3) | 0.9401 (2) | 0.0337 (2) | 0.0421 (7) | |
C17 | 0.4010 (3) | 0.9548 (3) | 0.0896 (3) | 0.0556 (8) | |
H17 | 0.4450 | 0.9010 | 0.1355 | 0.067* | |
C18 | 0.4677 (4) | 1.0491 (3) | 0.0784 (4) | 0.0726 (11) | |
H18 | 0.5557 | 1.0579 | 0.1170 | 0.087* | |
C19 | 0.4055 (5) | 1.1290 (3) | 0.0113 (4) | 0.0749 (11) | |
H19 | 0.4510 | 1.1917 | 0.0035 | 0.090* | |
C20 | 0.2742 (5) | 1.1160 (3) | −0.0449 (4) | 0.0765 (11) | |
H20 | 0.2309 | 1.1701 | −0.0907 | 0.092* | |
C21 | 0.2072 (4) | 1.0227 (3) | −0.0331 (3) | 0.0605 (9) | |
H21 | 0.1184 | 1.0150 | −0.0702 | 0.073* | |
C22 | 0.1743 (3) | 0.7793 (2) | −0.0816 (2) | 0.0375 (6) | |
C23 | 0.2647 (3) | 0.7935 (3) | −0.1602 (3) | 0.0493 (7) | |
H23 | 0.3330 | 0.8432 | −0.1437 | 0.059* | |
C24 | 0.2548 (4) | 0.7344 (3) | −0.2635 (3) | 0.0633 (10) | |
H24 | 0.3155 | 0.7458 | −0.3161 | 0.076* | |
C25 | 0.1568 (4) | 0.6597 (3) | −0.2886 (3) | 0.0671 (10) | |
H25 | 0.1507 | 0.6201 | −0.3577 | 0.081* | |
C26 | 0.0670 (4) | 0.6439 (3) | −0.2103 (3) | 0.0567 (9) | |
H26 | 0.0009 | 0.5923 | −0.2262 | 0.068* | |
C27 | 0.0741 (3) | 0.7036 (2) | −0.1088 (3) | 0.0457 (7) | |
H27 | 0.0114 | 0.6932 | −0.0578 | 0.055* | |
C28 | 0.0642 (3) | 0.8538 (2) | 0.0896 (2) | 0.0386 (7) | |
C29 | −0.0554 (3) | 0.8819 (2) | 0.0163 (3) | 0.0476 (7) | |
H29 | −0.0559 | 0.8893 | −0.0650 | 0.057* | |
C30 | −0.1736 (3) | 0.8991 (3) | 0.0631 (3) | 0.0570 (9) | |
H30 | −0.2518 | 0.9191 | 0.0133 | 0.068* | |
C31 | −0.1758 (4) | 0.8866 (3) | 0.1822 (4) | 0.0616 (9) | |
H31 | −0.2556 | 0.8958 | 0.2130 | 0.074* | |
C32 | −0.0587 (4) | 0.8605 (3) | 0.2554 (3) | 0.0598 (9) | |
H32 | −0.0594 | 0.8537 | 0.3365 | 0.072* | |
C33 | 0.0613 (4) | 0.8441 (2) | 0.2108 (3) | 0.0490 (8) | |
H33 | 0.1396 | 0.8267 | 0.2621 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0402 (13) | 0.0478 (15) | 0.0400 (13) | −0.0035 (12) | −0.0077 (11) | 0.0065 (12) |
N2 | 0.0393 (13) | 0.0308 (12) | 0.0372 (12) | −0.0020 (10) | −0.0039 (10) | −0.0003 (10) |
O1 | 0.0683 (15) | 0.0526 (15) | 0.0589 (14) | −0.0098 (13) | 0.0026 (12) | −0.0063 (12) |
O2 | 0.0602 (15) | 0.0829 (18) | 0.0675 (15) | −0.0324 (14) | 0.0033 (12) | 0.0164 (14) |
O3 | 0.0588 (13) | 0.0383 (11) | 0.0482 (12) | −0.0132 (10) | −0.0080 (10) | 0.0086 (9) |
O4 | 0.0354 (10) | 0.0887 (17) | 0.0431 (11) | −0.0179 (11) | 0.0094 (9) | −0.0213 (12) |
O5 | 0.0437 (11) | 0.0662 (15) | 0.0362 (10) | −0.0162 (11) | −0.0050 (9) | 0.0029 (10) |
O6 | 0.0488 (11) | 0.0363 (11) | 0.0373 (10) | −0.0024 (9) | −0.0053 (9) | 0.0074 (9) |
C1 | 0.0316 (14) | 0.0429 (16) | 0.0348 (14) | −0.0058 (13) | −0.0014 (11) | 0.0032 (13) |
C2 | 0.0319 (14) | 0.0570 (19) | 0.0564 (18) | 0.0005 (15) | 0.0034 (13) | −0.0037 (16) |
C3 | 0.0513 (19) | 0.057 (2) | 0.076 (2) | 0.0142 (17) | 0.0011 (18) | 0.0082 (19) |
C4 | 0.055 (2) | 0.075 (3) | 0.064 (2) | 0.010 (2) | −0.0141 (17) | 0.011 (2) |
C5 | 0.0522 (19) | 0.059 (2) | 0.0404 (17) | −0.0162 (17) | −0.0029 (14) | 0.0027 (16) |
C6 | 0.0444 (17) | 0.0497 (18) | 0.0405 (16) | −0.0117 (15) | −0.0009 (14) | 0.0021 (14) |
C7 | 0.0294 (13) | 0.0383 (14) | 0.0309 (13) | 0.0007 (12) | −0.0009 (11) | −0.0002 (12) |
C8 | 0.0316 (13) | 0.0394 (14) | 0.0318 (13) | −0.0007 (12) | 0.0030 (11) | −0.0007 (12) |
C9 | 0.0366 (14) | 0.0353 (14) | 0.0318 (13) | 0.0029 (12) | 0.0041 (11) | −0.0015 (12) |
C10 | 0.0341 (14) | 0.0342 (14) | 0.0333 (13) | 0.0023 (12) | 0.0027 (11) | 0.0003 (12) |
C11 | 0.0509 (17) | 0.0366 (15) | 0.0379 (15) | −0.0011 (14) | −0.0029 (13) | 0.0041 (12) |
C12 | 0.0352 (15) | 0.065 (2) | 0.0431 (16) | −0.0126 (14) | −0.0002 (13) | −0.0011 (15) |
C13 | 0.053 (2) | 0.197 (7) | 0.113 (4) | 0.045 (3) | 0.012 (3) | −0.001 (4) |
C14 | 0.136 (4) | 0.101 (3) | 0.055 (2) | −0.072 (3) | −0.007 (3) | 0.016 (2) |
C15 | 0.0471 (16) | 0.0331 (15) | 0.0311 (13) | 0.0026 (12) | 0.0017 (12) | 0.0028 (11) |
C16 | 0.0518 (18) | 0.0367 (15) | 0.0386 (15) | −0.0027 (14) | 0.0089 (13) | −0.0006 (13) |
C17 | 0.054 (2) | 0.0464 (19) | 0.065 (2) | −0.0097 (16) | 0.0045 (17) | −0.0006 (16) |
C18 | 0.066 (2) | 0.057 (2) | 0.093 (3) | −0.016 (2) | 0.007 (2) | −0.005 (2) |
C19 | 0.089 (3) | 0.044 (2) | 0.098 (3) | −0.023 (2) | 0.033 (3) | −0.005 (2) |
C20 | 0.099 (3) | 0.0391 (19) | 0.093 (3) | −0.002 (2) | 0.019 (3) | 0.016 (2) |
C21 | 0.070 (2) | 0.0412 (18) | 0.069 (2) | −0.0011 (17) | 0.0063 (18) | 0.0116 (17) |
C22 | 0.0450 (15) | 0.0332 (15) | 0.0325 (13) | 0.0077 (13) | 0.0000 (12) | 0.0033 (11) |
C23 | 0.0509 (18) | 0.054 (2) | 0.0436 (16) | 0.0055 (15) | 0.0090 (14) | 0.0020 (14) |
C24 | 0.072 (2) | 0.074 (3) | 0.0460 (18) | 0.025 (2) | 0.0155 (17) | −0.0031 (17) |
C25 | 0.090 (3) | 0.061 (2) | 0.0462 (18) | 0.024 (2) | −0.0043 (19) | −0.0189 (17) |
C26 | 0.070 (2) | 0.045 (2) | 0.0493 (18) | 0.0066 (16) | −0.0112 (17) | −0.0114 (15) |
C27 | 0.0561 (19) | 0.0398 (16) | 0.0383 (15) | 0.0025 (15) | −0.0020 (14) | −0.0004 (13) |
C28 | 0.0493 (17) | 0.0322 (14) | 0.0341 (14) | −0.0027 (13) | 0.0060 (13) | −0.0009 (12) |
C29 | 0.0528 (19) | 0.0430 (17) | 0.0466 (17) | 0.0053 (14) | 0.0059 (15) | 0.0040 (14) |
C30 | 0.0540 (19) | 0.0472 (19) | 0.070 (2) | 0.0029 (16) | 0.0111 (18) | 0.0034 (16) |
C31 | 0.065 (2) | 0.0458 (19) | 0.080 (3) | 0.0005 (17) | 0.031 (2) | −0.0005 (18) |
C32 | 0.085 (3) | 0.052 (2) | 0.0482 (18) | −0.0055 (19) | 0.0271 (19) | −0.0059 (15) |
C33 | 0.069 (2) | 0.0393 (16) | 0.0390 (15) | −0.0057 (15) | 0.0081 (15) | −0.0024 (13) |
N1—C5 | 1.333 (4) | C13—H13C | 0.9600 |
N1—C1 | 1.468 (3) | C14—H14A | 0.9600 |
N1—C4 | 1.472 (4) | C14—H14B | 0.9600 |
N2—O3 | 1.467 (3) | C14—H14C | 0.9600 |
N2—C7 | 1.487 (3) | C15—C16 | 1.535 (4) |
N2—C10 | 1.492 (3) | C15—C22 | 1.540 (4) |
O1—C5 | 1.217 (4) | C15—C28 | 1.541 (4) |
O2—C6 | 1.198 (4) | C16—C17 | 1.376 (4) |
O3—C6 | 1.351 (4) | C16—C21 | 1.392 (4) |
O4—C12 | 1.410 (3) | C17—C18 | 1.390 (5) |
O4—C8 | 1.417 (3) | C17—H17 | 0.9300 |
O5—C9 | 1.418 (3) | C18—C19 | 1.363 (6) |
O5—C12 | 1.425 (4) | C18—H18 | 0.9300 |
O6—C11 | 1.424 (3) | C19—C20 | 1.383 (6) |
O6—C15 | 1.448 (3) | C19—H19 | 0.9300 |
C1—C6 | 1.521 (4) | C20—C21 | 1.381 (5) |
C1—C7 | 1.535 (4) | C20—H20 | 0.9300 |
C1—C2 | 1.548 (4) | C21—H21 | 0.9300 |
C2—C3 | 1.511 (5) | C22—C23 | 1.382 (4) |
C2—H2A | 0.9700 | C22—C27 | 1.392 (4) |
C2—H2B | 0.9700 | C23—C24 | 1.388 (5) |
C3—C4 | 1.499 (5) | C23—H23 | 0.9300 |
C3—H3A | 0.9700 | C24—C25 | 1.365 (6) |
C3—H3B | 0.9700 | C24—H24 | 0.9300 |
C4—H4A | 0.9700 | C25—C26 | 1.378 (5) |
C4—H4B | 0.9700 | C25—H25 | 0.9300 |
C5—H5 | 0.9300 | C26—C27 | 1.378 (4) |
C7—C8 | 1.523 (4) | C26—H26 | 0.9300 |
C7—H7 | 0.9800 | C27—H27 | 0.9300 |
C8—C9 | 1.540 (4) | C28—C33 | 1.393 (4) |
C8—H8 | 0.9800 | C28—C29 | 1.398 (4) |
C9—C10 | 1.533 (4) | C29—C30 | 1.392 (4) |
C9—H9 | 0.9800 | C29—H29 | 0.9300 |
C10—C11 | 1.514 (4) | C30—C31 | 1.370 (5) |
C10—H10 | 0.9800 | C30—H30 | 0.9300 |
C11—H11A | 0.9700 | C31—C32 | 1.372 (5) |
C11—H11B | 0.9700 | C31—H31 | 0.9300 |
C12—C13 | 1.480 (6) | C32—C33 | 1.393 (5) |
C12—C14 | 1.508 (6) | C32—H32 | 0.9300 |
C13—H13A | 0.9600 | C33—H33 | 0.9300 |
C13—H13B | 0.9600 | ||
C5—N1—C1 | 122.4 (3) | O5—C12—C14 | 107.4 (3) |
C5—N1—C4 | 123.9 (3) | C13—C12—C14 | 114.8 (4) |
C1—N1—C4 | 112.8 (3) | C12—C13—H13A | 109.5 |
O3—N2—C7 | 105.12 (18) | C12—C13—H13B | 109.5 |
O3—N2—C10 | 107.6 (2) | H13A—C13—H13B | 109.5 |
C7—N2—C10 | 107.1 (2) | C12—C13—H13C | 109.5 |
C6—O3—N2 | 110.2 (2) | H13A—C13—H13C | 109.5 |
C12—O4—C8 | 109.7 (2) | H13B—C13—H13C | 109.5 |
C9—O5—C12 | 110.0 (2) | C12—C14—H14A | 109.5 |
C11—O6—C15 | 116.4 (2) | C12—C14—H14B | 109.5 |
N1—C1—C6 | 111.0 (2) | H14A—C14—H14B | 109.5 |
N1—C1—C7 | 113.4 (2) | C12—C14—H14C | 109.5 |
C6—C1—C7 | 101.5 (2) | H14A—C14—H14C | 109.5 |
N1—C1—C2 | 102.6 (2) | H14B—C14—H14C | 109.5 |
C6—C1—C2 | 111.4 (2) | O6—C15—C16 | 104.5 (2) |
C7—C1—C2 | 117.3 (2) | O6—C15—C22 | 107.6 (2) |
C3—C2—C1 | 104.9 (3) | C16—C15—C22 | 111.4 (2) |
C3—C2—H2A | 110.8 | O6—C15—C28 | 110.5 (2) |
C1—C2—H2A | 110.8 | C16—C15—C28 | 109.5 (2) |
C3—C2—H2B | 110.8 | C22—C15—C28 | 113.0 (2) |
C1—C2—H2B | 110.8 | C17—C16—C21 | 118.2 (3) |
H2A—C2—H2B | 108.8 | C17—C16—C15 | 122.0 (3) |
C4—C3—C2 | 104.6 (3) | C21—C16—C15 | 119.8 (3) |
C4—C3—H3A | 110.8 | C16—C17—C18 | 120.7 (3) |
C2—C3—H3A | 110.8 | C16—C17—H17 | 119.6 |
C4—C3—H3B | 110.8 | C18—C17—H17 | 119.6 |
C2—C3—H3B | 110.8 | C19—C18—C17 | 120.7 (4) |
H3A—C3—H3B | 108.9 | C19—C18—H18 | 119.6 |
N1—C4—C3 | 103.3 (2) | C17—C18—H18 | 119.6 |
N1—C4—H4A | 111.1 | C18—C19—C20 | 119.4 (4) |
C3—C4—H4A | 111.1 | C18—C19—H19 | 120.3 |
N1—C4—H4B | 111.1 | C20—C19—H19 | 120.3 |
C3—C4—H4B | 111.1 | C21—C20—C19 | 120.1 (4) |
H4A—C4—H4B | 109.1 | C21—C20—H20 | 120.0 |
O1—C5—N1 | 124.6 (3) | C19—C20—H20 | 120.0 |
O1—C5—H5 | 117.7 | C20—C21—C16 | 120.9 (3) |
N1—C5—H5 | 117.7 | C20—C21—H21 | 119.5 |
O2—C6—O3 | 121.3 (3) | C16—C21—H21 | 119.5 |
O2—C6—C1 | 127.7 (3) | C23—C22—C27 | 118.0 (3) |
O3—C6—C1 | 111.0 (2) | C23—C22—C15 | 120.3 (3) |
N2—C7—C8 | 103.65 (19) | C27—C22—C15 | 121.2 (3) |
N2—C7—C1 | 105.5 (2) | C22—C23—C24 | 120.8 (3) |
C8—C7—C1 | 118.6 (2) | C22—C23—H23 | 119.6 |
N2—C7—H7 | 109.5 | C24—C23—H23 | 119.6 |
C8—C7—H7 | 109.5 | C25—C24—C23 | 120.6 (3) |
C1—C7—H7 | 109.5 | C25—C24—H24 | 119.7 |
O4—C8—C7 | 108.1 (2) | C23—C24—H24 | 119.7 |
O4—C8—C9 | 104.1 (2) | C24—C25—C26 | 119.2 (3) |
C7—C8—C9 | 106.0 (2) | C24—C25—H25 | 120.4 |
O4—C8—H8 | 112.7 | C26—C25—H25 | 120.4 |
C7—C8—H8 | 112.7 | C27—C26—C25 | 120.7 (3) |
C9—C8—H8 | 112.7 | C27—C26—H26 | 119.7 |
O5—C9—C10 | 113.0 (2) | C25—C26—H26 | 119.7 |
O5—C9—C8 | 105.0 (2) | C26—C27—C22 | 120.7 (3) |
C10—C9—C8 | 106.4 (2) | C26—C27—H27 | 119.6 |
O5—C9—H9 | 110.7 | C22—C27—H27 | 119.6 |
C10—C9—H9 | 110.7 | C33—C28—C29 | 117.9 (3) |
C8—C9—H9 | 110.7 | C33—C28—C15 | 120.3 (3) |
N2—C10—C11 | 111.9 (2) | C29—C28—C15 | 121.7 (2) |
N2—C10—C9 | 103.86 (19) | C30—C29—C28 | 120.9 (3) |
C11—C10—C9 | 112.8 (2) | C30—C29—H29 | 119.6 |
N2—C10—H10 | 109.4 | C28—C29—H29 | 119.6 |
C11—C10—H10 | 109.4 | C31—C30—C29 | 120.5 (3) |
C9—C10—H10 | 109.4 | C31—C30—H30 | 119.7 |
O6—C11—C10 | 108.1 (2) | C29—C30—H30 | 119.7 |
O6—C11—H11A | 110.1 | C30—C31—C32 | 119.1 (3) |
C10—C11—H11A | 110.1 | C30—C31—H31 | 120.4 |
O6—C11—H11B | 110.1 | C32—C31—H31 | 120.4 |
C10—C11—H11B | 110.1 | C31—C32—C33 | 121.4 (3) |
H11A—C11—H11B | 108.4 | C31—C32—H32 | 119.3 |
O4—C12—O5 | 106.2 (2) | C33—C32—H32 | 119.3 |
O4—C12—C13 | 109.2 (3) | C28—C33—C32 | 120.1 (3) |
O5—C12—C13 | 108.9 (3) | C28—C33—H33 | 120.0 |
O4—C12—C14 | 110.0 (3) | C32—C33—H33 | 120.0 |
C7—N2—O3—C6 | 18.0 (3) | C15—O6—C11—C10 | −171.8 (2) |
C10—N2—O3—C6 | −95.9 (2) | N2—C10—C11—O6 | 52.3 (3) |
C5—N1—C1—C6 | 47.1 (4) | C9—C10—C11—O6 | 169.0 (2) |
C4—N1—C1—C6 | −122.4 (3) | C8—O4—C12—O5 | −23.0 (3) |
C5—N1—C1—C7 | −66.3 (4) | C8—O4—C12—C13 | −140.3 (3) |
C4—N1—C1—C7 | 124.2 (3) | C8—O4—C12—C14 | 92.9 (4) |
C5—N1—C1—C2 | 166.2 (3) | C9—O5—C12—O4 | 15.5 (3) |
C4—N1—C1—C2 | −3.3 (3) | C9—O5—C12—C13 | 133.0 (4) |
N1—C1—C2—C3 | 22.9 (3) | C9—O5—C12—C14 | −102.2 (3) |
C6—C1—C2—C3 | 141.7 (3) | C11—O6—C15—C16 | −177.0 (2) |
C7—C1—C2—C3 | −102.0 (3) | C11—O6—C15—C22 | −58.5 (3) |
C1—C2—C3—C4 | −34.4 (3) | C11—O6—C15—C28 | 65.3 (3) |
C5—N1—C4—C3 | 173.0 (3) | O6—C15—C16—C17 | 5.2 (4) |
C1—N1—C4—C3 | −17.7 (4) | C22—C15—C16—C17 | −110.7 (3) |
C2—C3—C4—N1 | 31.6 (4) | C28—C15—C16—C17 | 123.5 (3) |
C1—N1—C5—O1 | 3.9 (5) | O6—C15—C16—C21 | −176.9 (3) |
C4—N1—C5—O1 | 172.2 (3) | C22—C15—C16—C21 | 67.2 (3) |
N2—O3—C6—O2 | 176.9 (3) | C28—C15—C16—C21 | −58.5 (3) |
N2—O3—C6—C1 | −2.6 (3) | C21—C16—C17—C18 | −0.8 (5) |
N1—C1—C6—O2 | 46.7 (4) | C15—C16—C17—C18 | 177.2 (3) |
C7—C1—C6—O2 | 167.4 (3) | C16—C17—C18—C19 | −0.2 (6) |
C2—C1—C6—O2 | −67.0 (4) | C17—C18—C19—C20 | 0.7 (7) |
N1—C1—C6—O3 | −133.9 (2) | C18—C19—C20—C21 | −0.1 (6) |
C7—C1—C6—O3 | −13.2 (3) | C19—C20—C21—C16 | −1.0 (6) |
C2—C1—C6—O3 | 112.4 (3) | C17—C16—C21—C20 | 1.4 (5) |
O3—N2—C7—C8 | −151.0 (2) | C15—C16—C21—C20 | −176.6 (3) |
C10—N2—C7—C8 | −36.7 (3) | O6—C15—C22—C23 | −84.2 (3) |
O3—N2—C7—C1 | −25.6 (3) | C16—C15—C22—C23 | 29.8 (3) |
C10—N2—C7—C1 | 88.6 (2) | C28—C15—C22—C23 | 153.5 (3) |
N1—C1—C7—N2 | 142.4 (2) | O6—C15—C22—C27 | 87.4 (3) |
C6—C1—C7—N2 | 23.3 (3) | C16—C15—C22—C27 | −158.6 (3) |
C2—C1—C7—N2 | −98.3 (3) | C28—C15—C22—C27 | −34.8 (3) |
N1—C1—C7—C8 | −102.1 (3) | C27—C22—C23—C24 | 0.5 (4) |
C6—C1—C7—C8 | 138.8 (2) | C15—C22—C23—C24 | 172.5 (3) |
C2—C1—C7—C8 | 17.2 (3) | C22—C23—C24—C25 | −1.1 (5) |
C12—O4—C8—C7 | 133.2 (2) | C23—C24—C25—C26 | 0.3 (5) |
C12—O4—C8—C9 | 20.8 (3) | C24—C25—C26—C27 | 1.1 (5) |
N2—C7—C8—O4 | −86.4 (2) | C25—C26—C27—C22 | −1.7 (5) |
C1—C7—C8—O4 | 157.1 (2) | C23—C22—C27—C26 | 0.9 (4) |
N2—C7—C8—C9 | 24.7 (3) | C15—C22—C27—C26 | −171.0 (3) |
C1—C7—C8—C9 | −91.8 (3) | O6—C15—C28—C33 | 21.9 (4) |
C12—O5—C9—C10 | −118.3 (2) | C16—C15—C28—C33 | −92.7 (3) |
C12—O5—C9—C8 | −2.7 (3) | C22—C15—C28—C33 | 142.5 (3) |
O4—C8—C9—O5 | −10.8 (3) | O6—C15—C28—C29 | −158.9 (2) |
C7—C8—C9—O5 | −124.7 (2) | C16—C15—C28—C29 | 86.6 (3) |
O4—C8—C9—C10 | 109.2 (2) | C22—C15—C28—C29 | −38.3 (4) |
C7—C8—C9—C10 | −4.7 (3) | C33—C28—C29—C30 | −0.4 (4) |
O3—N2—C10—C11 | −91.9 (2) | C15—C28—C29—C30 | −179.6 (3) |
C7—N2—C10—C11 | 155.6 (2) | C28—C29—C30—C31 | −1.3 (5) |
O3—N2—C10—C9 | 146.18 (19) | C29—C30—C31—C32 | 2.2 (5) |
C7—N2—C10—C9 | 33.6 (2) | C30—C31—C32—C33 | −1.5 (5) |
O5—C9—C10—N2 | 97.7 (2) | C29—C28—C33—C32 | 1.1 (4) |
C8—C9—C10—N2 | −17.0 (3) | C15—C28—C33—C32 | −179.7 (3) |
O5—C9—C10—C11 | −23.7 (3) | C31—C32—C33—C28 | −0.2 (5) |
C8—C9—C10—C11 | −138.4 (2) |