Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047271/ez2046sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047271/ez2046Isup2.hkl |
CCDC reference: 617295
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.
C27H24N2O4 | F(000) = 1856 |
Mr = 440.48 | Dx = 1.349 Mg m−3 |
Monoclinic, C2/c | Melting point = 541–543 K |
Hall symbol: -C 2yc | Mo Kα radiation, λ = 0.71070 Å |
a = 28.768 (5) Å | Cell parameters from 7420 reflections |
b = 8.9966 (12) Å | θ = 3.1–25.3° |
c = 17.703 (3) Å | µ = 0.09 mm−1 |
β = 108.727 (4)° | T = 153 K |
V = 4339.2 (12) Å3 | Block, red |
Z = 8 | 0.64 × 0.26 × 0.15 mm |
Bruker SMART CCD area-detector diffractometer | 3964 independent reflections |
Radiation source: fine-focus sealed tube | 3408 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.043 |
φ and ω scans | θmax = 25.4°, θmin = 3.1° |
Absorption correction: multi-scan (Jacobson, 1998) | h = −34→34 |
Tmin = 0.743, Tmax = 0.986 | k = −10→10 |
20588 measured reflections | l = −21→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)] = 0.062 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.124 | H-atom parameters constrained |
S = 1.20 | w = 1/[σ2(Fo2) + (0.038P)2 + 3.838P] where P = (Fo2 + 2Fc2)/3 |
3964 reflections | (Δ/σ)max < 0.001 |
301 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.17 e Å−3 |
Experimental. IR (cm-1): 1677 (CO), 1647 (CO); 1H NMR (DMSO-d6): δ 8.10 (d, 2H, ArH, J = 8.4 Hz), 7.83 (d, 1H, ArH, J = 7.6 Hz), 7.48–7.46 (m, 2H, ArH), 7.36 (d, 2H, ArH, J = 8.4 Hz), 7.32 (d, 1H, ArH, J = 7.6 Hz), 4.62 (s, 1H, CH), 3.60 (t, 1H, CH, J = 3.2 Hz), 3.12 (d, 1H, CH2, J = 17.2 Hz), 2.75 (d, 1H, CH2, J = 17.2 Hz), 2.27 (d, 1H, CH2, J = 16.0 Hz), 2.20 (d, 1H, CH2, J = 16.0 Hz), 1.32–1.26 (m, 2H, CH2), 1.05 (s, 6H, CH3), 1.02–0.86 (m, 2H, CH2). |
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 | ||
O1 | 0.59592 (6) | 0.89038 (17) | 0.38693 (10) | 0.0477 (4) | |
O2 | 0.50781 (6) | 0.60749 (19) | 0.10337 (10) | 0.0494 (4) | |
O3 | 0.77112 (7) | 0.9309 (2) | 0.19556 (11) | 0.0615 (5) | |
O4 | 0.71474 (7) | 0.9855 (2) | 0.08579 (11) | 0.0634 (5) | |
N1 | 0.60501 (6) | 0.37340 (18) | 0.34188 (10) | 0.0314 (4) | |
N2 | 0.72809 (8) | 0.9310 (2) | 0.15266 (12) | 0.0441 (5) | |
C1 | 0.61193 (8) | 0.4984 (2) | 0.39193 (12) | 0.0315 (5) | |
C2 | 0.60067 (8) | 0.6369 (2) | 0.36130 (12) | 0.0324 (5) | |
C3 | 0.58334 (8) | 0.6692 (2) | 0.27249 (13) | 0.0349 (5) | |
H3A | 0.5558 | 0.7424 | 0.2615 | 0.042* | |
C4 | 0.56294 (8) | 0.5270 (2) | 0.23072 (12) | 0.0335 (5) | |
C5 | 0.57513 (8) | 0.3912 (2) | 0.26412 (12) | 0.0314 (5) | |
C6 | 0.60369 (8) | 0.7636 (2) | 0.41412 (14) | 0.0371 (5) | |
C7 | 0.61557 (9) | 0.7348 (3) | 0.50178 (13) | 0.0405 (6) | |
H7A | 0.5846 | 0.7163 | 0.5134 | 0.049* | |
H7B | 0.6308 | 0.8251 | 0.5315 | 0.049* | |
C8 | 0.64990 (8) | 0.6036 (2) | 0.53201 (12) | 0.0347 (5) | |
C9 | 0.62795 (8) | 0.4685 (2) | 0.48033 (12) | 0.0359 (5) | |
H9A | 0.6526 | 0.3877 | 0.4928 | 0.043* | |
H9B | 0.5993 | 0.4330 | 0.4946 | 0.043* | |
C10 | 0.52819 (8) | 0.5094 (3) | 0.15078 (13) | 0.0378 (5) | |
C11 | 0.52123 (8) | 0.3458 (3) | 0.13754 (13) | 0.0371 (5) | |
C12 | 0.49206 (8) | 0.2698 (3) | 0.07211 (14) | 0.0446 (6) | |
H12 | 0.4748 | 0.3208 | 0.0243 | 0.053* | |
C13 | 0.48846 (9) | 0.1159 (3) | 0.07775 (15) | 0.0475 (6) | |
H13 | 0.4684 | 0.0608 | 0.0334 | 0.057* | |
C14 | 0.51376 (9) | 0.0436 (3) | 0.14703 (14) | 0.0453 (6) | |
H14 | 0.5099 | −0.0608 | 0.1505 | 0.054* | |
C15 | 0.54519 (8) | 0.1200 (3) | 0.21289 (14) | 0.0392 (5) | |
H15 | 0.5633 | 0.0683 | 0.2599 | 0.047* | |
C16 | 0.54902 (8) | 0.2722 (2) | 0.20733 (12) | 0.0339 (5) | |
C17 | 0.62256 (8) | 0.7353 (2) | 0.24130 (13) | 0.0339 (5) | |
C18 | 0.67197 (8) | 0.7356 (2) | 0.28623 (13) | 0.0372 (5) | |
H18 | 0.6821 | 0.6921 | 0.3379 | 0.045* | |
C19 | 0.70670 (9) | 0.7981 (3) | 0.25718 (13) | 0.0393 (5) | |
H19 | 0.7405 | 0.7975 | 0.2882 | 0.047* | |
C20 | 0.69137 (9) | 0.8613 (2) | 0.18234 (13) | 0.0367 (5) | |
C21 | 0.64292 (9) | 0.8606 (2) | 0.13516 (14) | 0.0422 (6) | |
H21 | 0.6332 | 0.9028 | 0.0832 | 0.051* | |
C22 | 0.60887 (9) | 0.7973 (2) | 0.16510 (14) | 0.0407 (6) | |
H22 | 0.5753 | 0.7959 | 0.1331 | 0.049* | |
C23 | 0.70126 (8) | 0.6371 (3) | 0.52797 (14) | 0.0426 (6) | |
H23A | 0.6995 | 0.6515 | 0.4722 | 0.064* | |
H23B | 0.7232 | 0.5536 | 0.5507 | 0.064* | |
H23C | 0.7140 | 0.7276 | 0.5584 | 0.064* | |
C24 | 0.65375 (9) | 0.5700 (3) | 0.61857 (13) | 0.0450 (6) | |
H24A | 0.6665 | 0.6575 | 0.6517 | 0.068* | |
H24B | 0.6760 | 0.4859 | 0.6380 | 0.068* | |
H24C | 0.6212 | 0.5452 | 0.6214 | 0.068* | |
C25 | 0.62573 (8) | 0.2288 (2) | 0.37083 (12) | 0.0337 (5) | |
H25 | 0.6055 | 0.1627 | 0.3933 | 0.040* | |
C26 | 0.65556 (8) | 0.1540 (3) | 0.32669 (13) | 0.0412 (6) | |
H26A | 0.6600 | 0.2068 | 0.2804 | 0.049* | |
H26B | 0.6532 | 0.0445 | 0.3214 | 0.049* | |
C27 | 0.68037 (9) | 0.2170 (3) | 0.40780 (14) | 0.0439 (6) | |
H27A | 0.7000 | 0.3086 | 0.4115 | 0.053* | |
H27B | 0.6933 | 0.1464 | 0.4525 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0654 (11) | 0.0266 (9) | 0.0567 (10) | 0.0058 (8) | 0.0273 (9) | 0.0006 (8) |
O2 | 0.0460 (10) | 0.0522 (11) | 0.0455 (10) | 0.0103 (8) | 0.0082 (8) | 0.0122 (8) |
O3 | 0.0612 (12) | 0.0781 (14) | 0.0508 (11) | −0.0238 (11) | 0.0258 (10) | −0.0066 (10) |
O4 | 0.0789 (13) | 0.0606 (12) | 0.0618 (12) | 0.0033 (10) | 0.0383 (11) | 0.0255 (10) |
N1 | 0.0404 (10) | 0.0255 (9) | 0.0294 (10) | 0.0006 (8) | 0.0125 (8) | 0.0003 (7) |
N2 | 0.0663 (15) | 0.0307 (11) | 0.0455 (13) | −0.0053 (10) | 0.0321 (11) | −0.0029 (9) |
C1 | 0.0363 (11) | 0.0279 (11) | 0.0341 (12) | −0.0023 (9) | 0.0166 (10) | −0.0024 (9) |
C2 | 0.0375 (12) | 0.0281 (11) | 0.0360 (12) | 0.0017 (9) | 0.0180 (10) | 0.0000 (9) |
C3 | 0.0407 (12) | 0.0290 (11) | 0.0388 (12) | 0.0074 (10) | 0.0181 (10) | 0.0047 (9) |
C4 | 0.0370 (12) | 0.0319 (12) | 0.0353 (12) | 0.0034 (10) | 0.0168 (10) | 0.0028 (9) |
C5 | 0.0336 (11) | 0.0327 (12) | 0.0313 (12) | 0.0005 (9) | 0.0150 (9) | −0.0011 (9) |
C6 | 0.0388 (12) | 0.0300 (12) | 0.0482 (14) | 0.0007 (10) | 0.0218 (11) | −0.0019 (10) |
C7 | 0.0501 (14) | 0.0369 (13) | 0.0409 (13) | −0.0024 (11) | 0.0236 (11) | −0.0082 (10) |
C8 | 0.0458 (13) | 0.0310 (12) | 0.0316 (12) | −0.0062 (10) | 0.0186 (10) | −0.0043 (9) |
C9 | 0.0476 (13) | 0.0319 (12) | 0.0311 (12) | −0.0064 (10) | 0.0166 (10) | −0.0008 (9) |
C10 | 0.0344 (12) | 0.0449 (14) | 0.0363 (13) | 0.0062 (11) | 0.0146 (10) | 0.0047 (11) |
C11 | 0.0323 (11) | 0.0445 (14) | 0.0364 (13) | 0.0008 (10) | 0.0136 (10) | −0.0007 (10) |
C12 | 0.0340 (12) | 0.0609 (17) | 0.0375 (13) | 0.0028 (12) | 0.0095 (11) | −0.0026 (12) |
C13 | 0.0395 (13) | 0.0570 (17) | 0.0457 (15) | −0.0038 (12) | 0.0132 (11) | −0.0164 (12) |
C14 | 0.0429 (13) | 0.0449 (14) | 0.0497 (15) | −0.0058 (12) | 0.0173 (12) | −0.0125 (12) |
C15 | 0.0403 (13) | 0.0385 (13) | 0.0406 (13) | −0.0021 (11) | 0.0154 (11) | −0.0071 (10) |
C16 | 0.0330 (11) | 0.0384 (13) | 0.0340 (12) | −0.0008 (10) | 0.0158 (10) | −0.0041 (9) |
C17 | 0.0450 (13) | 0.0233 (11) | 0.0379 (13) | 0.0052 (10) | 0.0196 (10) | 0.0008 (9) |
C18 | 0.0485 (13) | 0.0334 (12) | 0.0338 (12) | 0.0033 (11) | 0.0191 (11) | 0.0030 (9) |
C19 | 0.0474 (13) | 0.0381 (13) | 0.0359 (13) | 0.0000 (11) | 0.0184 (11) | −0.0019 (10) |
C20 | 0.0536 (14) | 0.0235 (11) | 0.0408 (13) | −0.0007 (10) | 0.0259 (11) | −0.0016 (9) |
C21 | 0.0603 (16) | 0.0317 (13) | 0.0393 (13) | 0.0054 (11) | 0.0225 (12) | 0.0104 (10) |
C22 | 0.0464 (13) | 0.0358 (13) | 0.0410 (13) | 0.0055 (11) | 0.0154 (11) | 0.0063 (10) |
C23 | 0.0432 (13) | 0.0475 (14) | 0.0394 (13) | −0.0079 (11) | 0.0166 (11) | −0.0025 (11) |
C24 | 0.0574 (15) | 0.0460 (14) | 0.0366 (13) | −0.0090 (12) | 0.0220 (11) | −0.0057 (11) |
C25 | 0.0418 (12) | 0.0232 (11) | 0.0369 (12) | 0.0021 (9) | 0.0137 (10) | 0.0022 (9) |
C26 | 0.0476 (14) | 0.0350 (13) | 0.0427 (14) | 0.0057 (11) | 0.0170 (11) | −0.0017 (10) |
C27 | 0.0435 (13) | 0.0434 (14) | 0.0418 (14) | 0.0056 (11) | 0.0096 (11) | 0.0014 (11) |
O1—C6 | 1.230 (3) | C12—H12 | 0.9500 |
O2—C10 | 1.229 (3) | C13—C14 | 1.372 (3) |
O3—N2 | 1.227 (3) | C13—H13 | 0.9500 |
O4—N2 | 1.223 (3) | C14—C15 | 1.404 (3) |
N1—C5 | 1.378 (3) | C14—H14 | 0.9500 |
N1—C1 | 1.406 (3) | C15—C16 | 1.381 (3) |
N1—C25 | 1.454 (3) | C15—H15 | 0.9500 |
N2—C20 | 1.463 (3) | C17—C18 | 1.388 (3) |
C1—C2 | 1.356 (3) | C17—C22 | 1.395 (3) |
C1—C9 | 1.507 (3) | C18—C19 | 1.382 (3) |
C2—C6 | 1.459 (3) | C18—H18 | 0.9500 |
C2—C3 | 1.517 (3) | C19—C20 | 1.377 (3) |
C3—C4 | 1.500 (3) | C19—H19 | 0.9500 |
C3—C17 | 1.527 (3) | C20—C21 | 1.376 (3) |
C3—H3A | 1.0000 | C21—C22 | 1.378 (3) |
C4—C5 | 1.354 (3) | C21—H21 | 0.9500 |
C4—C10 | 1.456 (3) | C22—H22 | 0.9500 |
C5—C16 | 1.495 (3) | C23—H23A | 0.9800 |
C6—C7 | 1.500 (3) | C23—H23B | 0.9800 |
C7—C8 | 1.522 (3) | C23—H23C | 0.9800 |
C7—H7A | 0.9900 | C24—H24A | 0.9800 |
C7—H7B | 0.9900 | C24—H24B | 0.9800 |
C8—C9 | 1.530 (3) | C24—H24C | 0.9800 |
C8—C24 | 1.531 (3) | C25—C26 | 1.493 (3) |
C8—C23 | 1.532 (3) | C25—C27 | 1.500 (3) |
C9—H9A | 0.9900 | C25—H25 | 1.0000 |
C9—H9B | 0.9900 | C26—C27 | 1.495 (3) |
C10—C11 | 1.494 (3) | C26—H26A | 0.9900 |
C11—C12 | 1.374 (3) | C26—H26B | 0.9900 |
C11—C16 | 1.403 (3) | C27—H27A | 0.9900 |
C12—C13 | 1.395 (4) | C27—H27B | 0.9900 |
C5—N1—C1 | 116.97 (17) | C13—C14—C15 | 121.7 (2) |
C5—N1—C25 | 120.62 (17) | C13—C14—H14 | 119.1 |
C1—N1—C25 | 122.31 (17) | C15—C14—H14 | 119.1 |
O4—N2—O3 | 122.7 (2) | C16—C15—C14 | 118.1 (2) |
O4—N2—C20 | 118.7 (2) | C16—C15—H15 | 121.0 |
O3—N2—C20 | 118.6 (2) | C14—C15—H15 | 121.0 |
C2—C1—N1 | 121.05 (19) | C15—C16—C11 | 119.7 (2) |
C2—C1—C9 | 122.25 (19) | C15—C16—C5 | 134.2 (2) |
N1—C1—C9 | 116.47 (17) | C11—C16—C5 | 106.02 (19) |
C1—C2—C6 | 120.27 (19) | C18—C17—C22 | 118.2 (2) |
C1—C2—C3 | 123.18 (19) | C18—C17—C3 | 122.22 (19) |
C6—C2—C3 | 116.53 (18) | C22—C17—C3 | 119.6 (2) |
C4—C3—C2 | 107.09 (17) | C19—C18—C17 | 121.2 (2) |
C4—C3—C17 | 111.81 (17) | C19—C18—H18 | 119.4 |
C2—C3—C17 | 114.47 (18) | C17—C18—H18 | 119.4 |
C4—C3—H3A | 107.7 | C20—C19—C18 | 118.6 (2) |
C2—C3—H3A | 107.7 | C20—C19—H19 | 120.7 |
C17—C3—H3A | 107.7 | C18—C19—H19 | 120.7 |
C5—C4—C10 | 109.07 (19) | C21—C20—C19 | 122.1 (2) |
C5—C4—C3 | 123.33 (19) | C21—C20—N2 | 119.4 (2) |
C10—C4—C3 | 127.60 (19) | C19—C20—N2 | 118.5 (2) |
C4—C5—N1 | 122.12 (19) | C20—C21—C22 | 118.4 (2) |
C4—C5—C16 | 110.41 (18) | C20—C21—H21 | 120.8 |
N1—C5—C16 | 127.32 (19) | C22—C21—H21 | 120.8 |
O1—C6—C2 | 120.5 (2) | C21—C22—C17 | 121.5 (2) |
O1—C6—C7 | 121.1 (2) | C21—C22—H22 | 119.2 |
C2—C6—C7 | 118.36 (19) | C17—C22—H22 | 119.2 |
C6—C7—C8 | 113.83 (18) | C8—C23—H23A | 109.5 |
C6—C7—H7A | 108.8 | C8—C23—H23B | 109.5 |
C8—C7—H7A | 108.8 | H23A—C23—H23B | 109.5 |
C6—C7—H7B | 108.8 | C8—C23—H23C | 109.5 |
C8—C7—H7B | 108.8 | H23A—C23—H23C | 109.5 |
H7A—C7—H7B | 107.7 | H23B—C23—H23C | 109.5 |
C7—C8—C9 | 108.01 (18) | C8—C24—H24A | 109.5 |
C7—C8—C24 | 109.58 (18) | C8—C24—H24B | 109.5 |
C9—C8—C24 | 108.98 (18) | H24A—C24—H24B | 109.5 |
C7—C8—C23 | 110.96 (18) | C8—C24—H24C | 109.5 |
C9—C8—C23 | 110.33 (18) | H24A—C24—H24C | 109.5 |
C24—C8—C23 | 108.95 (19) | H24B—C24—H24C | 109.5 |
C1—C9—C8 | 114.13 (17) | N1—C25—C26 | 117.26 (18) |
C1—C9—H9A | 108.7 | N1—C25—C27 | 118.09 (19) |
C8—C9—H9A | 108.7 | C26—C25—C27 | 59.91 (15) |
C1—C9—H9B | 108.7 | N1—C25—H25 | 116.5 |
C8—C9—H9B | 108.7 | C26—C25—H25 | 116.5 |
H9A—C9—H9B | 107.6 | C27—C25—H25 | 116.5 |
O2—C10—C4 | 127.9 (2) | C25—C26—C27 | 60.26 (15) |
O2—C10—C11 | 126.1 (2) | C25—C26—H26A | 117.7 |
C4—C10—C11 | 105.99 (19) | C27—C26—H26A | 117.7 |
C12—C11—C16 | 121.9 (2) | C25—C26—H26B | 117.7 |
C12—C11—C10 | 129.6 (2) | C27—C26—H26B | 117.7 |
C16—C11—C10 | 108.47 (19) | H26A—C26—H26B | 114.9 |
C11—C12—C13 | 118.2 (2) | C26—C27—C25 | 59.83 (14) |
C11—C12—H12 | 120.9 | C26—C27—H27A | 117.8 |
C13—C12—H12 | 120.9 | C25—C27—H27A | 117.8 |
C14—C13—C12 | 120.3 (2) | C26—C27—H27B | 117.8 |
C14—C13—H13 | 119.9 | C25—C27—H27B | 117.8 |
C12—C13—H13 | 119.9 | H27A—C27—H27B | 114.9 |
C5—N1—C1—C2 | −16.5 (3) | C4—C10—C11—C12 | 179.6 (2) |
C25—N1—C1—C2 | 167.0 (2) | O2—C10—C11—C16 | −176.9 (2) |
C5—N1—C1—C9 | 158.16 (18) | C4—C10—C11—C16 | 2.2 (2) |
C25—N1—C1—C9 | −18.3 (3) | C16—C11—C12—C13 | 3.4 (3) |
N1—C1—C2—C6 | 174.19 (19) | C10—C11—C12—C13 | −173.8 (2) |
C9—C1—C2—C6 | −0.1 (3) | C11—C12—C13—C14 | −0.3 (4) |
N1—C1—C2—C3 | −4.2 (3) | C12—C13—C14—C15 | −2.4 (4) |
C9—C1—C2—C3 | −178.54 (19) | C13—C14—C15—C16 | 2.0 (3) |
C1—C2—C3—C4 | 21.9 (3) | C14—C15—C16—C11 | 1.0 (3) |
C6—C2—C3—C4 | −156.53 (18) | C14—C15—C16—C5 | 175.5 (2) |
C1—C2—C3—C17 | −102.6 (2) | C12—C11—C16—C15 | −3.7 (3) |
C6—C2—C3—C17 | 78.9 (2) | C10—C11—C16—C15 | 174.0 (2) |
C2—C3—C4—C5 | −22.1 (3) | C12—C11—C16—C5 | −179.6 (2) |
C17—C3—C4—C5 | 104.0 (2) | C10—C11—C16—C5 | −1.9 (2) |
C2—C3—C4—C10 | 158.0 (2) | C4—C5—C16—C15 | −174.0 (2) |
C17—C3—C4—C10 | −75.9 (3) | N1—C5—C16—C15 | 1.7 (4) |
C10—C4—C5—N1 | −175.60 (18) | C4—C5—C16—C11 | 1.0 (2) |
C3—C4—C5—N1 | 4.5 (3) | N1—C5—C16—C11 | 176.71 (19) |
C10—C4—C5—C16 | 0.3 (2) | C4—C3—C17—C18 | −108.8 (2) |
C3—C4—C5—C16 | −179.57 (19) | C2—C3—C17—C18 | 13.2 (3) |
C1—N1—C5—C4 | 16.5 (3) | C4—C3—C17—C22 | 71.0 (2) |
C25—N1—C5—C4 | −167.0 (2) | C2—C3—C17—C22 | −167.04 (19) |
C1—N1—C5—C16 | −158.72 (19) | C22—C17—C18—C19 | 1.2 (3) |
C25—N1—C5—C16 | 17.8 (3) | C3—C17—C18—C19 | −179.02 (19) |
C1—C2—C6—O1 | 176.3 (2) | C17—C18—C19—C20 | 0.3 (3) |
C3—C2—C6—O1 | −5.2 (3) | C18—C19—C20—C21 | −1.7 (3) |
C1—C2—C6—C7 | −4.8 (3) | C18—C19—C20—N2 | 178.33 (19) |
C3—C2—C6—C7 | 173.73 (19) | O4—N2—C20—C21 | −1.0 (3) |
O1—C6—C7—C8 | −148.0 (2) | O3—N2—C20—C21 | 179.8 (2) |
C2—C6—C7—C8 | 33.1 (3) | O4—N2—C20—C19 | 179.0 (2) |
C6—C7—C8—C9 | −53.3 (2) | O3—N2—C20—C19 | −0.2 (3) |
C6—C7—C8—C24 | −171.95 (19) | C19—C20—C21—C22 | 1.5 (3) |
C6—C7—C8—C23 | 67.7 (2) | N2—C20—C21—C22 | −178.54 (19) |
C2—C1—C9—C8 | −23.2 (3) | C20—C21—C22—C17 | 0.1 (3) |
N1—C1—C9—C8 | 162.17 (18) | C18—C17—C22—C21 | −1.5 (3) |
C7—C8—C9—C1 | 48.3 (2) | C3—C17—C22—C21 | 178.8 (2) |
C24—C8—C9—C1 | 167.25 (19) | C5—N1—C25—C26 | 56.3 (3) |
C23—C8—C9—C1 | −73.2 (2) | C1—N1—C25—C26 | −127.4 (2) |
C5—C4—C10—O2 | 177.6 (2) | C5—N1—C25—C27 | 124.9 (2) |
C3—C4—C10—O2 | −2.5 (4) | C1—N1—C25—C27 | −58.8 (3) |
C5—C4—C10—C11 | −1.5 (2) | N1—C25—C26—C27 | 108.3 (2) |
C3—C4—C10—C11 | 178.4 (2) | N1—C25—C27—C26 | −106.9 (2) |
O2—C10—C11—C12 | 0.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C27—H27B···O4i | 0.99 | 2.53 | 3.496 (3) | 164 |
C27—H27A···O3ii | 0.99 | 2.55 | 3.262 (3) | 129 |
C12—H12···O2iii | 0.95 | 2.55 | 3.298 (3) | 136 |
Symmetry codes: (i) x, −y+1, z+1/2; (ii) −x+3/2, y−1/2, −z+1/2; (iii) −x+1, −y+1, −z. |