organic compounds
In the title compound, C23H28N2O9, the substituted 1,4-dihydropyridine ring has a flat-boat conformation. The dihedral angle between the mean planes of the 1,4-dihydropyridine and substituted phenyl rings is 88.10 (9)°. The 3-nitro substituent on the phenyl ring is rotated from coplanarity with the ring by only 3.2 (2)°.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803003015/lh6034sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803003015/lh6034Isup2.hkl |
CCDC reference: 206771
Computing details top
Data collection: Syntex P21 software; cell refinement: Syntex P21 software; data reduction: XP21 (Pavelčík, 1987); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXS97.
2,3-Dimethyl 5-isopropyl 1-ethoxymethyl-6-methyl-4-(3-nitrophenyl)-1,4-
dihydropyridine-2,3,5-tricarboxylate top
Crystal data top
C23H28N2O9 | F(000) = 1008 |
Mr = 476.47 | Dx = 1.325 Mg m−3 Dm = 1.33 (1) Mg m−3 Dm measured by flotation in bromoform–hexane |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
a = 9.291 (4) Å | θ = 6.9–18.7° |
b = 9.589 (3) Å | µ = 0.10 mm−1 |
c = 27.175 (13) Å | T = 293 K |
β = 99.53 (3)° | Block, yellow |
V = 2387.6 (17) Å3 | 0.4 × 0.3 × 0.3 mm |
Z = 4 |
Data collection top
Syntex P21 diffractometer | Rint = 0.000 |
Radiation source: fine-focus sealed tube | θmax = 27.6°, θmin = 1.5° |
Graphite monochromator | h = 0→12 |
θ/2θ scans | k = 0→12 |
5519 measured reflections | l = −35→34 |
5519 independent reflections | 2 standard reflections every 100 min |
1503 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.059 | H-atom parameters constrained |
wR(F2) = 0.083 | w = 1/[σ2(Fo2) + (0.0187P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.93 | (Δ/σ)max = 0.004 |
5519 reflections | Δρmax = 0.21 e Å−3 |
313 parameters | Δρmin = −0.16 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0027 (2) |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.7279 (3) | −0.4152 (2) | 0.67898 (9) | 0.0956 (7) | |
O2 | 0.5845 (2) | −0.2275 (2) | 0.79432 (6) | 0.0943 (8) | |
O3 | 0.8117 (2) | −0.23776 (18) | 0.77752 (6) | 0.0681 (6) | |
O4 | 0.74316 (19) | 0.05575 (17) | 0.78769 (5) | 0.0746 (6) | |
O5 | 0.7679 (2) | 0.1972 (2) | 0.72510 (6) | 0.0647 (6) | |
O6 | 0.7651 (2) | 0.3403 (2) | 0.51954 (7) | 0.0844 (7) | |
O7 | 0.9599 (2) | 0.2487 (2) | 0.50037 (6) | 0.0872 (7) | |
O8 | 0.2915 (2) | −0.04339 (18) | 0.55522 (7) | 0.0818 (7) | |
O9 | 0.41566 (17) | 0.14887 (18) | 0.57961 (5) | 0.0509 (5) | |
N1 | 0.5540 (2) | −0.2373 (2) | 0.68197 (7) | 0.0527 (6) | |
N2 | 0.8597 (3) | 0.2523 (3) | 0.52454 (8) | 0.0626 (7) | |
C1 | 0.6297 (3) | −0.1459 (3) | 0.71601 (8) | 0.0460 (7) | |
C2 | 0.6513 (3) | −0.0145 (3) | 0.70464 (8) | 0.0426 (7) | |
C3 | 0.6097 (2) | 0.0382 (2) | 0.65277 (7) | 0.0414 (6) | |
H3 | 0.5743 | 0.1341 | 0.6545 | 0.050* | |
C4 | 0.4848 (2) | −0.0502 (3) | 0.62581 (8) | 0.0410 (7) | |
C5 | 0.4680 (3) | −0.1832 (3) | 0.63865 (9) | 0.0454 (7) | |
C6 | 0.5879 (3) | −0.3856 (3) | 0.68790 (10) | 0.0710 (9) | |
H6A | 0.5795 | −0.4142 | 0.7215 | 0.085* | |
H6B | 0.5176 | −0.4386 | 0.6649 | 0.085* | |
C7 | 0.7411 (4) | −0.4476 (4) | 0.63160 (12) | 0.1120 (13) | |
H7A | 0.7024 | −0.3719 | 0.6096 | 0.134* | |
H7B | 0.6843 | −0.5306 | 0.6213 | 0.134* | |
C8 | 0.8964 (4) | −0.4725 (3) | 0.62678 (11) | 0.1196 (12) | |
H8A | 0.9024 | −0.4955 | 0.5928 | 0.179* | |
H8B | 0.9344 | −0.5482 | 0.6481 | 0.179* | |
H8C | 0.9523 | −0.3898 | 0.6363 | 0.179* | |
C9 | 0.6712 (4) | −0.2069 (3) | 0.76746 (9) | 0.0589 (8) | |
C10 | 0.8600 (3) | −0.2995 (3) | 0.82578 (9) | 0.1065 (12) | |
H10A | 0.9615 | −0.3234 | 0.8290 | 0.160* | |
H10B | 0.8041 | −0.3822 | 0.8291 | 0.160* | |
H10C | 0.8467 | −0.2342 | 0.8514 | 0.160* | |
C11 | 0.7239 (3) | 0.0806 (3) | 0.74377 (10) | 0.0544 (8) | |
C12 | 0.8348 (3) | 0.2998 (3) | 0.76061 (9) | 0.0950 (11) | |
H12A | 0.8479 | 0.3853 | 0.7435 | 0.142* | |
H12B | 0.9279 | 0.2661 | 0.7769 | 0.142* | |
H12C | 0.7729 | 0.3162 | 0.7850 | 0.142* | |
C13 | 0.7348 (3) | 0.0391 (3) | 0.62293 (8) | 0.0386 (6) | |
C14 | 0.7456 (3) | 0.1443 (2) | 0.58971 (8) | 0.0412 (7) | |
H14 | 0.6801 | 0.2184 | 0.5865 | 0.049* | |
C15 | 0.8547 (3) | 0.1393 (3) | 0.56097 (9) | 0.0455 (7) | |
C16 | 0.9559 (3) | 0.0352 (3) | 0.56523 (9) | 0.0543 (7) | |
H16 | 1.0293 | 0.0345 | 0.5457 | 0.065* | |
C17 | 0.9460 (3) | −0.0681 (3) | 0.59904 (9) | 0.0535 (7) | |
H17 | 1.0129 | −0.1410 | 0.6026 | 0.064* | |
C18 | 0.8373 (3) | −0.0647 (3) | 0.62785 (8) | 0.0499 (7) | |
H18 | 0.8335 | −0.1347 | 0.6513 | 0.060* | |
C19 | 0.3870 (3) | 0.0138 (3) | 0.58384 (9) | 0.0484 (7) | |
C20 | 0.3283 (3) | 0.2257 (3) | 0.53940 (9) | 0.0625 (8) | |
H20 | 0.2266 | 0.1943 | 0.5352 | 0.075* | |
C21 | 0.3386 (4) | 0.3747 (3) | 0.55625 (10) | 0.1195 (13) | |
H21A | 0.2668 | 0.4292 | 0.5351 | 0.179* | |
H21B | 0.4342 | 0.4100 | 0.5544 | 0.179* | |
H21C | 0.3214 | 0.3802 | 0.5901 | 0.179* | |
C22 | 0.3874 (3) | 0.2032 (3) | 0.49220 (9) | 0.1130 (12) | |
H22A | 0.4856 | 0.2379 | 0.4961 | 0.170* | |
H22B | 0.3278 | 0.2518 | 0.4654 | 0.170* | |
H22C | 0.3870 | 0.1053 | 0.4848 | 0.170* | |
C23 | 0.3559 (3) | −0.2825 (2) | 0.61175 (8) | 0.0640 (8) | |
H23A | 0.3654 | −0.3715 | 0.6282 | 0.096* | |
H23B | 0.3711 | −0.2933 | 0.5779 | 0.096* | |
H23C | 0.2599 | −0.2460 | 0.6121 | 0.096* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0896 (18) | 0.0818 (16) | 0.1119 (17) | 0.0077 (15) | 0.0063 (16) | −0.0159 (14) |
O2 | 0.0787 (15) | 0.144 (2) | 0.0624 (12) | −0.0194 (15) | 0.0183 (11) | 0.0406 (13) |
O3 | 0.0605 (14) | 0.0805 (15) | 0.0590 (11) | 0.0127 (13) | −0.0025 (10) | 0.0183 (11) |
O4 | 0.1057 (16) | 0.0789 (15) | 0.0357 (10) | −0.0017 (13) | 0.0012 (11) | −0.0031 (11) |
O5 | 0.0820 (15) | 0.0591 (13) | 0.0509 (11) | −0.0178 (12) | 0.0053 (10) | −0.0026 (11) |
O6 | 0.0968 (18) | 0.0739 (16) | 0.0874 (15) | 0.0177 (14) | 0.0293 (14) | 0.0347 (13) |
O7 | 0.0755 (16) | 0.1144 (18) | 0.0783 (13) | −0.0121 (15) | 0.0321 (13) | 0.0256 (13) |
O8 | 0.0690 (14) | 0.0651 (15) | 0.0963 (14) | −0.0141 (13) | −0.0299 (12) | 0.0100 (11) |
O9 | 0.0565 (13) | 0.0417 (11) | 0.0502 (10) | −0.0002 (11) | −0.0045 (9) | 0.0048 (10) |
N1 | 0.0580 (16) | 0.0440 (15) | 0.0540 (14) | −0.0009 (14) | 0.0030 (12) | 0.0134 (13) |
N2 | 0.064 (2) | 0.072 (2) | 0.0507 (15) | −0.0132 (18) | 0.0059 (15) | 0.0115 (16) |
C1 | 0.0419 (18) | 0.058 (2) | 0.0380 (16) | −0.0013 (17) | 0.0062 (14) | 0.0040 (17) |
C2 | 0.0423 (18) | 0.0473 (19) | 0.0383 (15) | 0.0006 (15) | 0.0069 (14) | 0.0015 (14) |
C3 | 0.0434 (16) | 0.0392 (17) | 0.0415 (14) | 0.0015 (15) | 0.0067 (14) | −0.0021 (14) |
C4 | 0.0368 (16) | 0.049 (2) | 0.0367 (14) | −0.0013 (17) | 0.0054 (13) | 0.0044 (15) |
C5 | 0.0426 (18) | 0.0444 (19) | 0.0505 (17) | −0.0043 (16) | 0.0114 (15) | 0.0008 (15) |
C6 | 0.071 (2) | 0.059 (2) | 0.081 (2) | 0.001 (2) | 0.0070 (19) | 0.0130 (17) |
C7 | 0.117 (3) | 0.136 (3) | 0.079 (2) | −0.014 (3) | 0.004 (2) | −0.029 (2) |
C8 | 0.099 (3) | 0.125 (3) | 0.134 (3) | 0.026 (3) | 0.015 (2) | −0.034 (2) |
C9 | 0.066 (2) | 0.061 (2) | 0.0471 (19) | −0.009 (2) | 0.0012 (18) | 0.0111 (16) |
C10 | 0.111 (3) | 0.124 (3) | 0.0708 (19) | 0.014 (2) | −0.0276 (19) | 0.049 (2) |
C11 | 0.0549 (19) | 0.064 (2) | 0.0442 (17) | 0.0036 (18) | 0.0083 (16) | −0.0035 (19) |
C12 | 0.133 (3) | 0.077 (2) | 0.0686 (19) | −0.042 (2) | −0.003 (2) | −0.0202 (18) |
C13 | 0.0413 (16) | 0.0387 (17) | 0.0344 (14) | 0.0071 (16) | 0.0025 (13) | 0.0036 (13) |
C14 | 0.0424 (17) | 0.0434 (17) | 0.0379 (13) | 0.0018 (15) | 0.0066 (14) | −0.0005 (14) |
C15 | 0.0446 (18) | 0.0453 (19) | 0.0444 (16) | −0.0079 (17) | 0.0007 (15) | 0.0027 (16) |
C16 | 0.0446 (18) | 0.070 (2) | 0.0502 (16) | −0.0078 (19) | 0.0132 (15) | −0.0029 (17) |
C17 | 0.0486 (19) | 0.054 (2) | 0.0594 (16) | 0.0080 (17) | 0.0126 (16) | 0.0010 (16) |
C18 | 0.0547 (18) | 0.0517 (19) | 0.0437 (15) | −0.0024 (18) | 0.0096 (14) | 0.0043 (15) |
C19 | 0.0456 (19) | 0.046 (2) | 0.0531 (18) | 0.0016 (18) | 0.0081 (15) | −0.0007 (16) |
C20 | 0.0489 (18) | 0.057 (2) | 0.073 (2) | 0.0017 (18) | −0.0140 (16) | 0.0155 (18) |
C21 | 0.188 (4) | 0.049 (2) | 0.106 (2) | 0.013 (3) | −0.020 (2) | 0.0113 (19) |
C22 | 0.117 (3) | 0.151 (3) | 0.0637 (19) | 0.003 (3) | −0.004 (2) | 0.032 (2) |
C23 | 0.068 (2) | 0.0572 (19) | 0.0640 (17) | −0.0137 (18) | 0.0024 (16) | 0.0047 (15) |
Geometric parameters (Å, º) top
O1—C7 | 1.350 (3) | C8—H8A | 0.9600 |
O1—C6 | 1.391 (3) | C8—H8B | 0.9600 |
O2—C9 | 1.190 (3) | C8—H8C | 0.9600 |
O3—C9 | 1.322 (3) | C10—H10A | 0.9600 |
O3—C10 | 1.441 (2) | C10—H10B | 0.9600 |
O4—C11 | 1.201 (2) | C10—H10C | 0.9600 |
O5—C11 | 1.321 (3) | C12—H12A | 0.9600 |
O5—C12 | 1.445 (2) | C12—H12B | 0.9600 |
O6—N2 | 1.210 (3) | C12—H12C | 0.9600 |
O7—N2 | 1.225 (2) | C13—C14 | 1.369 (3) |
O8—C19 | 1.211 (3) | C13—C18 | 1.369 (3) |
O9—C19 | 1.331 (3) | C14—C15 | 1.380 (3) |
O9—C20 | 1.450 (2) | C14—H14 | 0.9300 |
N1—C1 | 1.380 (3) | C15—C16 | 1.363 (3) |
N1—C5 | 1.408 (3) | C16—C17 | 1.364 (3) |
N1—C6 | 1.459 (3) | C16—H16 | 0.9300 |
N2—C15 | 1.474 (3) | C17—C18 | 1.376 (3) |
C1—C2 | 1.320 (3) | C17—H17 | 0.9300 |
C1—C9 | 1.506 (3) | C18—H18 | 0.9300 |
C2—C11 | 1.476 (3) | C20—C22 | 1.492 (3) |
C2—C3 | 1.487 (3) | C20—C21 | 1.498 (3) |
C3—C4 | 1.523 (3) | C20—H20 | 0.9800 |
C3—C13 | 1.523 (3) | C21—H21A | 0.9600 |
C3—H3 | 0.9800 | C21—H21B | 0.9600 |
C4—C5 | 1.339 (3) | C21—H21C | 0.9600 |
C4—C19 | 1.470 (3) | C22—H22A | 0.9600 |
C5—C23 | 1.508 (3) | C22—H22B | 0.9600 |
C6—H6A | 0.9700 | C22—H22C | 0.9600 |
C6—H6B | 0.9700 | C23—H23A | 0.9600 |
C7—C8 | 1.489 (4) | C23—H23B | 0.9600 |
C7—H7A | 0.9700 | C23—H23C | 0.9600 |
C7—H7B | 0.9700 | ||
C7—O1—C6 | 116.7 (3) | O4—C11—O5 | 123.0 (3) |
C9—O3—C10 | 115.4 (2) | O4—C11—C2 | 124.7 (3) |
C11—O5—C12 | 116.52 (19) | O5—C11—C2 | 112.3 (2) |
C19—O9—C20 | 117.7 (2) | O5—C12—H12A | 109.5 |
C1—N1—C5 | 118.8 (2) | O5—C12—H12B | 109.5 |
C1—N1—C6 | 117.9 (2) | H12A—C12—H12B | 109.5 |
C5—N1—C6 | 122.2 (2) | O5—C12—H12C | 109.5 |
O6—N2—O7 | 124.2 (3) | H12A—C12—H12C | 109.5 |
O6—N2—C15 | 119.0 (3) | H12B—C12—H12C | 109.5 |
O7—N2—C15 | 116.8 (3) | C14—C13—C18 | 118.3 (2) |
C2—C1—N1 | 122.0 (2) | C14—C13—C3 | 120.1 (2) |
C2—C1—C9 | 124.2 (3) | C18—C13—C3 | 121.6 (2) |
N1—C1—C9 | 113.5 (2) | C13—C14—C15 | 119.3 (2) |
C1—C2—C11 | 119.3 (2) | C13—C14—H14 | 120.4 |
C1—C2—C3 | 121.4 (2) | C15—C14—H14 | 120.4 |
C11—C2—C3 | 119.3 (2) | C16—C15—C14 | 122.6 (2) |
C2—C3—C4 | 109.0 (2) | C16—C15—N2 | 119.9 (3) |
C2—C3—C13 | 113.86 (19) | C14—C15—N2 | 117.5 (3) |
C4—C3—C13 | 109.53 (17) | C15—C16—C17 | 117.8 (2) |
C2—C3—H3 | 108.1 | C15—C16—H16 | 121.1 |
C4—C3—H3 | 108.1 | C17—C16—H16 | 121.1 |
C13—C3—H3 | 108.1 | C16—C17—C18 | 120.2 (2) |
C5—C4—C19 | 121.1 (3) | C16—C17—H17 | 119.9 |
C5—C4—C3 | 121.2 (2) | C18—C17—H17 | 119.9 |
C19—C4—C3 | 117.7 (2) | C13—C18—C17 | 121.7 (2) |
C4—C5—N1 | 119.6 (2) | C13—C18—H18 | 119.1 |
C4—C5—C23 | 125.2 (2) | C17—C18—H18 | 119.1 |
N1—C5—C23 | 115.1 (2) | O8—C19—O9 | 121.4 (2) |
O1—C6—N1 | 111.8 (2) | O8—C19—C4 | 127.1 (3) |
O1—C6—H6A | 109.3 | O9—C19—C4 | 111.5 (3) |
N1—C6—H6A | 109.3 | O9—C20—C22 | 109.5 (2) |
O1—C6—H6B | 109.3 | O9—C20—C21 | 104.8 (2) |
N1—C6—H6B | 109.3 | C22—C20—C21 | 112.8 (3) |
H6A—C6—H6B | 107.9 | O9—C20—H20 | 109.9 |
O1—C7—C8 | 111.3 (3) | C22—C20—H20 | 109.9 |
O1—C7—H7A | 109.4 | C21—C20—H20 | 109.9 |
C8—C7—H7A | 109.4 | C20—C21—H21A | 109.5 |
O1—C7—H7B | 109.4 | C20—C21—H21B | 109.5 |
C8—C7—H7B | 109.4 | H21A—C21—H21B | 109.5 |
H7A—C7—H7B | 108.0 | C20—C21—H21C | 109.5 |
C7—C8—H8A | 109.5 | H21A—C21—H21C | 109.5 |
C7—C8—H8B | 109.5 | H21B—C21—H21C | 109.5 |
H8A—C8—H8B | 109.5 | C20—C22—H22A | 109.5 |
C7—C8—H8C | 109.5 | C20—C22—H22B | 109.5 |
H8A—C8—H8C | 109.5 | H22A—C22—H22B | 109.5 |
H8B—C8—H8C | 109.5 | C20—C22—H22C | 109.5 |
O2—C9—O3 | 125.5 (3) | H22A—C22—H22C | 109.5 |
O2—C9—C1 | 122.6 (3) | H22B—C22—H22C | 109.5 |
O3—C9—C1 | 111.8 (2) | C5—C23—H23A | 109.5 |
O3—C10—H10A | 109.5 | C5—C23—H23B | 109.5 |
O3—C10—H10B | 109.5 | H23A—C23—H23B | 109.5 |
H10A—C10—H10B | 109.5 | C5—C23—H23C | 109.5 |
O3—C10—H10C | 109.5 | H23A—C23—H23C | 109.5 |
H10A—C10—H10C | 109.5 | H23B—C23—H23C | 109.5 |
H10B—C10—H10C | 109.5 | ||
C5—N1—C1—C2 | −15.6 (3) | N1—C1—C9—O3 | 105.3 (3) |
C6—N1—C1—C2 | 153.2 (3) | C12—O5—C11—O4 | −3.4 (4) |
C5—N1—C1—C9 | 159.0 (2) | C12—O5—C11—C2 | 177.4 (2) |
C6—N1—C1—C9 | −32.2 (3) | C1—C2—C11—O4 | −13.8 (4) |
N1—C1—C2—C11 | 175.6 (2) | C3—C2—C11—O4 | 168.8 (2) |
C9—C1—C2—C11 | 1.6 (4) | C1—C2—C11—O5 | 165.4 (2) |
N1—C1—C2—C3 | −7.0 (4) | C3—C2—C11—O5 | −12.0 (3) |
C9—C1—C2—C3 | 179.0 (2) | C2—C3—C13—C14 | −143.6 (2) |
C1—C2—C3—C4 | 26.8 (3) | C4—C3—C13—C14 | 94.1 (3) |
C11—C2—C3—C4 | −155.7 (2) | C2—C3—C13—C18 | 37.3 (3) |
C1—C2—C3—C13 | −95.8 (3) | C4—C3—C13—C18 | −84.9 (2) |
C11—C2—C3—C13 | 81.7 (3) | C18—C13—C14—C15 | 2.8 (3) |
C2—C3—C4—C5 | −27.8 (3) | C3—C13—C14—C15 | −176.36 (19) |
C13—C3—C4—C5 | 97.3 (3) | C13—C14—C15—C16 | −1.9 (3) |
C2—C3—C4—C19 | 154.7 (2) | C13—C14—C15—N2 | 178.11 (19) |
C13—C3—C4—C19 | −80.1 (2) | O6—N2—C15—C16 | 176.5 (2) |
C19—C4—C5—N1 | −173.71 (19) | O7—N2—C15—C16 | −2.1 (3) |
C3—C4—C5—N1 | 8.9 (3) | O6—N2—C15—C14 | −3.5 (3) |
C19—C4—C5—C23 | 2.6 (4) | O7—N2—C15—C14 | 177.8 (2) |
C3—C4—C5—C23 | −174.8 (2) | C14—C15—C16—C17 | 0.8 (4) |
C1—N1—C5—C4 | 14.2 (3) | N2—C15—C16—C17 | −179.3 (2) |
C6—N1—C5—C4 | −154.1 (3) | C15—C16—C17—C18 | −0.5 (4) |
C1—N1—C5—C23 | −162.4 (2) | C14—C13—C18—C17 | −2.6 (3) |
C6—N1—C5—C23 | 29.2 (3) | C3—C13—C18—C17 | 176.5 (2) |
C7—O1—C6—N1 | −90.3 (3) | C16—C17—C18—C13 | 1.5 (4) |
C1—N1—C6—O1 | −67.5 (3) | C20—O9—C19—O8 | 0.0 (3) |
C5—N1—C6—O1 | 101.0 (3) | C20—O9—C19—C4 | 179.48 (18) |
C6—O1—C7—C8 | 178.2 (3) | C5—C4—C19—O8 | −5.0 (4) |
C10—O3—C9—O2 | −1.0 (4) | C3—C4—C19—O8 | 172.4 (2) |
C10—O3—C9—C1 | −178.8 (2) | C5—C4—C19—O9 | 175.5 (2) |
C2—C1—C9—O2 | 101.9 (4) | C3—C4—C19—O9 | −7.0 (3) |
N1—C1—C9—O2 | −72.6 (4) | C19—O9—C20—C22 | −82.1 (3) |
C2—C1—C9—O3 | −80.3 (3) | C19—O9—C20—C21 | 156.7 (2) |