Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013898/bt6292sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013898/bt6292Isup2.hkl |
CCDC reference: 221673
Key indicators
- Single-crystal X-ray study
- T = 133 K
- Mean (C-C) = 0.002 Å
- R factor = 0.042
- wR factor = 0.116
- Data-to-parameter ratio = 19.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_320 Alert C Check Hybridisation of C1 in Main Residue . ? PLAT_320 Alert C Check Hybridisation of C5 in Main Residue . ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP (Siemens, 1994); software used to prepare material for publication: SHELXL97.
C30H48N4O4 | Z = 2 |
Mr = 528.72 | F(000) = 576 |
Triclinic, P1 | Dx = 1.176 Mg m−3 |
a = 10.8375 (8) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 11.6922 (8) Å | Cell parameters from 6653 reflections |
c = 13.7337 (10) Å | θ = 2.2–28.5° |
α = 109.065 (3)° | µ = 0.08 mm−1 |
β = 101.073 (3)° | T = 133 K |
γ = 106.800 (3)° | Prism, colourless |
V = 1493.59 (19) Å3 | 0.39 × 0.23 × 0.19 mm |
Bruker SMART 1000 CCD diffractometer | 5396 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 28.3°, θmin = 1.7° |
Detector resolution: 8.192 pixels mm-1 | h = −14→14 |
ω–scan | k = −15→15 |
17805 measured reflections | l = −18→18 |
7353 independent reflections |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.116 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0586P)2 + 0.0907P] where P = (Fo2 + 2Fc2)/3 |
7353 reflections | (Δ/σ)max = 0.001 |
373 parameters | Δρmax = 0.42 e Å−3 |
3 restraints | Δρmin = −0.33 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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 9.1385 (0.0020) x - 1.4857 (0.0039) y + 3.5543 (0.0046) z = 3.0982 (0.0022) * -0.0484 (0.0006) C11 * 0.0487 (0.0006) C16 * -0.0496 (0.0006) C21 * 0.0493 (0.0006) C26 - 0.9638 (0.0013) O1 0.6964 (0.0016) O2 - 0.9108 (0.0014) O3 0.7314 (0.0015) O4 Rms deviation of fitted atoms = 0.0490 |
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 | Occ. (<1) | |
O1 | 0.20249 (9) | 0.78494 (9) | 0.40800 (7) | 0.0303 (2) | |
O2 | 0.38325 (9) | 0.38040 (8) | 0.24123 (8) | 0.0325 (2) | |
O3 | 0.30457 (9) | 0.50436 (9) | 0.04316 (7) | 0.0332 (2) | |
O4 | 0.44982 (9) | 1.01521 (8) | 0.34527 (7) | 0.0287 (2) | |
N1 | 0.29341 (10) | 0.70016 (10) | 0.51542 (8) | 0.0240 (2) | |
N2 | 0.18476 (11) | 0.40507 (10) | 0.23941 (10) | 0.0357 (3) | |
N3 | 0.46959 (11) | 0.68472 (10) | 0.05547 (8) | 0.0277 (2) | |
N4 | 0.27657 (11) | 0.87143 (10) | 0.19391 (9) | 0.0283 (2) | |
C1 | 0.38238 (11) | 0.72177 (11) | 0.36999 (9) | 0.0197 (2) | |
C2 | 0.52392 (11) | 0.82734 (11) | 0.40662 (9) | 0.0193 (2) | |
H2 | 0.5513 | 0.9128 | 0.4696 | 0.023* | |
C3 | 0.62373 (11) | 0.76636 (11) | 0.38673 (9) | 0.0202 (2) | |
C4 | 0.53939 (11) | 0.64552 (11) | 0.28906 (9) | 0.0208 (2) | |
H4 | 0.5798 | 0.5823 | 0.2547 | 0.025* | |
C5 | 0.39286 (11) | 0.59675 (11) | 0.28954 (9) | 0.0203 (2) | |
C6 | 0.43074 (11) | 0.67008 (11) | 0.21909 (9) | 0.0203 (2) | |
C7 | 0.42035 (11) | 0.79429 (11) | 0.29908 (9) | 0.0193 (2) | |
C8 | 0.75585 (12) | 0.80992 (12) | 0.44102 (10) | 0.0241 (2) | |
C9 | 0.82600 (13) | 0.93387 (13) | 0.54204 (11) | 0.0338 (3) | |
H9A | 0.7589 | 0.9692 | 0.5633 | 0.041* | |
H9B | 0.8933 | 0.9979 | 0.5282 | 0.041* | |
H9C | 0.8716 | 0.9156 | 0.6007 | 0.041* | |
C10 | 0.84586 (12) | 0.73922 (13) | 0.40492 (12) | 0.0321 (3) | |
H10A | 0.7916 | 0.6585 | 0.3399 | 0.039* | |
H10B | 0.8870 | 0.7177 | 0.4631 | 0.039* | |
H10C | 0.9176 | 0.7954 | 0.3882 | 0.039* | |
C11 | 0.28542 (11) | 0.73851 (11) | 0.43291 (9) | 0.0217 (2) | |
C12 | 0.19938 (13) | 0.71676 (13) | 0.57739 (11) | 0.0324 (3) | |
H12A | 0.1886 | 0.6545 | 0.6126 | 0.039* | |
H12B | 0.1093 | 0.6946 | 0.5266 | 0.039* | |
C13 | 0.24526 (16) | 0.85370 (16) | 0.66354 (13) | 0.0464 (4) | |
H13A | 0.3344 | 0.8766 | 0.7142 | 0.056* | |
H13B | 0.1793 | 0.8576 | 0.7032 | 0.056* | |
H13C | 0.2517 | 0.9156 | 0.6290 | 0.056* | |
C14 | 0.40144 (13) | 0.66079 (12) | 0.55725 (10) | 0.0282 (3) | |
H14A | 0.4434 | 0.7140 | 0.6364 | 0.034* | |
H14B | 0.4726 | 0.6789 | 0.5225 | 0.034* | |
C15 | 0.35012 (15) | 0.51725 (14) | 0.53655 (13) | 0.0396 (3) | |
H15A | 0.2771 | 0.4980 | 0.5683 | 0.048* | |
H15B | 0.4248 | 0.4969 | 0.5698 | 0.048* | |
H15C | 0.3153 | 0.4639 | 0.4581 | 0.048* | |
C16 | 0.31929 (12) | 0.45210 (12) | 0.25344 (10) | 0.0251 (3) | |
C17 | 0.1234 (2) | 0.26610 (19) | 0.2222 (2) | 0.0314 (6) | 0.756 (5) |
H17A | 0.0568 | 0.2565 | 0.2622 | 0.038* | 0.756 (5) |
H17B | 0.1951 | 0.2381 | 0.2509 | 0.038* | 0.756 (5) |
C18 | 0.0537 (3) | 0.1813 (2) | 0.1035 (2) | 0.0570 (8) | 0.756 (5) |
H18A | −0.0181 | 0.2084 | 0.0756 | 0.068* | 0.756 (5) |
H18B | 0.0137 | 0.0898 | 0.0932 | 0.068* | 0.756 (5) |
H18C | 0.1200 | 0.1902 | 0.0642 | 0.068* | 0.756 (5) |
C17' | 0.1000 (6) | 0.2618 (6) | 0.1660 (6) | 0.0297 (17) | 0.244 (5) |
H17C | 0.0082 | 0.2490 | 0.1242 | 0.036* | 0.244 (5) |
H17D | 0.1455 | 0.2233 | 0.1156 | 0.036* | 0.244 (5) |
C18' | 0.0955 (6) | 0.2072 (6) | 0.2532 (6) | 0.045 (2) | 0.244 (5) |
H18D | 0.1878 | 0.2200 | 0.2916 | 0.054* | 0.244 (5) |
H18E | 0.0388 | 0.1136 | 0.2188 | 0.054* | 0.244 (5) |
H18F | 0.0570 | 0.2530 | 0.3049 | 0.054* | 0.244 (5) |
C19 | 0.09622 (13) | 0.47470 (13) | 0.22217 (12) | 0.0332 (3) | |
H19A | 0.0434 | 0.4360 | 0.1441 | 0.040* | |
H19B | 0.1529 | 0.5672 | 0.2422 | 0.040* | |
C20 | −0.00118 (14) | 0.46942 (15) | 0.28792 (14) | 0.0418 (4) | |
H20A | −0.0678 | 0.3798 | 0.2599 | 0.050* | |
H20B | −0.0485 | 0.5280 | 0.2821 | 0.050* | |
H20C | 0.0497 | 0.4971 | 0.3642 | 0.050* | |
C21 | 0.39500 (12) | 0.61257 (12) | 0.09818 (10) | 0.0239 (2) | |
C22 | 0.58444 (13) | 0.80895 (12) | 0.12003 (11) | 0.0295 (3) | |
H22A | 0.5748 | 0.8477 | 0.1925 | 0.035* | |
H22B | 0.5817 | 0.8699 | 0.0845 | 0.035* | |
C23 | 0.72126 (14) | 0.79567 (15) | 0.13429 (13) | 0.0435 (4) | |
H23A | 0.7280 | 0.7418 | 0.1752 | 0.052* | |
H23B | 0.7940 | 0.8825 | 0.1741 | 0.052* | |
H23C | 0.7302 | 0.7542 | 0.0628 | 0.052* | |
C24 | 0.44416 (15) | 0.63029 (15) | −0.06204 (10) | 0.0368 (3) | |
H24A | 0.3992 | 0.5339 | −0.0915 | 0.044* | |
H24B | 0.5320 | 0.6512 | −0.0768 | 0.044* | |
C25 | 0.35664 (19) | 0.6826 (2) | −0.11906 (13) | 0.0590 (5) | |
H25A | 0.2680 | 0.6587 | −0.1074 | 0.071* | |
H25B | 0.3442 | 0.6452 | −0.1970 | 0.071* | |
H25C | 0.4006 | 0.7781 | −0.0900 | 0.071* | |
C26 | 0.38140 (11) | 0.90130 (11) | 0.28165 (9) | 0.0215 (2) | |
C27 | 0.25626 (15) | 0.98161 (14) | 0.17382 (12) | 0.0374 (3) | |
H27A | 0.2801 | 1.0556 | 0.2443 | 0.045* | |
H27B | 0.1591 | 0.9553 | 0.1347 | 0.045* | |
C28 | 0.3401 (2) | 1.02584 (19) | 0.10872 (17) | 0.0594 (5) | |
H28A | 0.4361 | 1.0481 | 0.1453 | 0.071* | |
H28B | 0.3280 | 1.1030 | 0.1018 | 0.071* | |
H28C | 0.3112 | 0.9554 | 0.0363 | 0.071* | |
C29 | 0.17208 (13) | 0.74177 (13) | 0.12725 (11) | 0.0316 (3) | |
H29A | 0.2042 | 0.6758 | 0.1412 | 0.038* | |
H29B | 0.1583 | 0.7251 | 0.0497 | 0.038* | |
C30 | 0.03673 (14) | 0.72489 (16) | 0.14871 (13) | 0.0438 (4) | |
H30A | 0.0491 | 0.7394 | 0.2250 | 0.053* | |
H30B | −0.0290 | 0.6360 | 0.1018 | 0.053* | |
H30C | 0.0029 | 0.7883 | 0.1332 | 0.053* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0295 (5) | 0.0371 (5) | 0.0346 (5) | 0.0207 (4) | 0.0162 (4) | 0.0164 (4) |
O2 | 0.0338 (5) | 0.0222 (4) | 0.0448 (6) | 0.0137 (4) | 0.0181 (4) | 0.0116 (4) |
O3 | 0.0308 (5) | 0.0300 (5) | 0.0254 (5) | 0.0066 (4) | 0.0063 (4) | 0.0011 (4) |
O4 | 0.0362 (5) | 0.0218 (4) | 0.0280 (5) | 0.0129 (4) | 0.0098 (4) | 0.0086 (4) |
N1 | 0.0236 (5) | 0.0267 (5) | 0.0257 (5) | 0.0103 (4) | 0.0139 (4) | 0.0114 (4) |
N2 | 0.0255 (6) | 0.0203 (5) | 0.0564 (8) | 0.0063 (5) | 0.0181 (5) | 0.0089 (5) |
N3 | 0.0332 (6) | 0.0299 (6) | 0.0202 (5) | 0.0133 (5) | 0.0118 (4) | 0.0073 (4) |
N4 | 0.0302 (5) | 0.0302 (6) | 0.0284 (6) | 0.0172 (5) | 0.0071 (4) | 0.0127 (5) |
C1 | 0.0204 (5) | 0.0194 (5) | 0.0212 (6) | 0.0088 (5) | 0.0090 (4) | 0.0078 (5) |
C2 | 0.0198 (5) | 0.0188 (5) | 0.0186 (5) | 0.0074 (4) | 0.0070 (4) | 0.0061 (4) |
C3 | 0.0222 (5) | 0.0205 (6) | 0.0216 (6) | 0.0093 (5) | 0.0101 (5) | 0.0100 (5) |
C4 | 0.0209 (5) | 0.0207 (6) | 0.0233 (6) | 0.0100 (5) | 0.0105 (5) | 0.0083 (5) |
C5 | 0.0201 (5) | 0.0199 (6) | 0.0223 (6) | 0.0094 (5) | 0.0100 (4) | 0.0070 (5) |
C6 | 0.0207 (5) | 0.0206 (6) | 0.0196 (6) | 0.0088 (5) | 0.0080 (4) | 0.0062 (5) |
C7 | 0.0203 (5) | 0.0202 (6) | 0.0182 (5) | 0.0096 (5) | 0.0084 (4) | 0.0058 (4) |
C8 | 0.0212 (6) | 0.0230 (6) | 0.0295 (6) | 0.0087 (5) | 0.0093 (5) | 0.0114 (5) |
C9 | 0.0235 (6) | 0.0299 (7) | 0.0372 (8) | 0.0081 (6) | 0.0042 (5) | 0.0056 (6) |
C10 | 0.0211 (6) | 0.0294 (7) | 0.0462 (8) | 0.0109 (5) | 0.0122 (6) | 0.0136 (6) |
C11 | 0.0207 (5) | 0.0201 (6) | 0.0227 (6) | 0.0075 (5) | 0.0094 (5) | 0.0056 (5) |
C12 | 0.0325 (7) | 0.0362 (7) | 0.0333 (7) | 0.0115 (6) | 0.0218 (6) | 0.0146 (6) |
C13 | 0.0474 (9) | 0.0469 (9) | 0.0417 (9) | 0.0149 (7) | 0.0294 (7) | 0.0080 (7) |
C14 | 0.0290 (6) | 0.0321 (7) | 0.0287 (7) | 0.0130 (5) | 0.0112 (5) | 0.0163 (6) |
C15 | 0.0463 (8) | 0.0360 (8) | 0.0430 (8) | 0.0175 (7) | 0.0140 (7) | 0.0222 (7) |
C16 | 0.0272 (6) | 0.0214 (6) | 0.0270 (6) | 0.0091 (5) | 0.0129 (5) | 0.0078 (5) |
C17 | 0.0264 (10) | 0.0233 (11) | 0.0387 (14) | 0.0045 (8) | 0.0067 (10) | 0.0121 (11) |
C18 | 0.0614 (15) | 0.0258 (13) | 0.0554 (16) | 0.0100 (11) | −0.0108 (12) | 0.0048 (13) |
C17' | 0.023 (3) | 0.022 (4) | 0.027 (4) | 0.004 (3) | 0.006 (3) | −0.004 (4) |
C18' | 0.040 (4) | 0.030 (3) | 0.080 (5) | 0.015 (3) | 0.034 (3) | 0.031 (4) |
C19 | 0.0233 (6) | 0.0266 (7) | 0.0400 (8) | 0.0064 (5) | 0.0105 (6) | 0.0044 (6) |
C20 | 0.0262 (7) | 0.0344 (8) | 0.0574 (10) | 0.0082 (6) | 0.0191 (7) | 0.0092 (7) |
C21 | 0.0235 (6) | 0.0266 (6) | 0.0224 (6) | 0.0132 (5) | 0.0089 (5) | 0.0067 (5) |
C22 | 0.0343 (7) | 0.0285 (7) | 0.0290 (7) | 0.0119 (6) | 0.0178 (6) | 0.0112 (5) |
C23 | 0.0346 (8) | 0.0412 (9) | 0.0519 (9) | 0.0125 (7) | 0.0204 (7) | 0.0133 (7) |
C24 | 0.0472 (8) | 0.0427 (8) | 0.0221 (7) | 0.0187 (7) | 0.0171 (6) | 0.0102 (6) |
C25 | 0.0594 (10) | 0.0945 (14) | 0.0290 (8) | 0.0404 (11) | 0.0124 (8) | 0.0234 (9) |
C26 | 0.0241 (6) | 0.0250 (6) | 0.0219 (6) | 0.0135 (5) | 0.0125 (5) | 0.0105 (5) |
C27 | 0.0441 (8) | 0.0415 (8) | 0.0384 (8) | 0.0278 (7) | 0.0112 (6) | 0.0213 (7) |
C28 | 0.0774 (12) | 0.0665 (12) | 0.0738 (13) | 0.0454 (11) | 0.0397 (10) | 0.0513 (11) |
C29 | 0.0277 (6) | 0.0370 (7) | 0.0269 (7) | 0.0153 (6) | 0.0043 (5) | 0.0089 (6) |
C30 | 0.0287 (7) | 0.0539 (10) | 0.0493 (9) | 0.0199 (7) | 0.0090 (6) | 0.0198 (8) |
O1—C11 | 1.2267 (14) | C14—C15 | 1.5149 (19) |
O2—C16 | 1.2248 (14) | C14—H14A | 0.9900 |
O3—C21 | 1.2274 (15) | C14—H14B | 0.9900 |
O4—C26 | 1.2277 (14) | C15—H15A | 0.9800 |
N1—C11 | 1.3451 (15) | C15—H15B | 0.9800 |
N1—C14 | 1.4624 (15) | C15—H15C | 0.9800 |
N1—C12 | 1.4629 (15) | C17—C18 | 1.500 (3) |
N2—C16 | 1.3508 (16) | C17—H17A | 0.9900 |
N2—C19 | 1.4593 (17) | C17—H17B | 0.9900 |
N2—C17 | 1.484 (2) | C18—H18A | 0.9800 |
N2—C17' | 1.522 (6) | C18—H18B | 0.9800 |
N3—C21 | 1.3493 (15) | C18—H18C | 0.9800 |
N3—C22 | 1.4611 (16) | C17'—C18' | 1.532 (9) |
N3—C24 | 1.4636 (16) | C17'—H17C | 0.9900 |
N4—C26 | 1.3544 (15) | C17'—H17D | 0.9900 |
N4—C29 | 1.4565 (17) | C18'—H18D | 0.9800 |
N4—C27 | 1.4686 (16) | C18'—H18E | 0.9800 |
C1—C11 | 1.4987 (15) | C18'—H18F | 0.9800 |
C1—C7 | 1.5259 (15) | C19—C20 | 1.5160 (19) |
C1—C2 | 1.5274 (15) | C19—H19A | 0.9900 |
C1—C5 | 1.5683 (16) | C19—H19B | 0.9900 |
C2—C3 | 1.4782 (15) | C20—H20A | 0.9800 |
C2—C7 | 1.5264 (15) | C20—H20B | 0.9800 |
C2—H2 | 1.0000 | C20—H20C | 0.9800 |
C3—C8 | 1.3363 (16) | C22—C23 | 1.5175 (19) |
C3—C4 | 1.4749 (16) | C22—H22A | 0.9900 |
C4—C5 | 1.5264 (15) | C22—H22B | 0.9900 |
C4—C6 | 1.5276 (15) | C23—H23A | 0.9800 |
C4—H4 | 1.0000 | C23—H23B | 0.9800 |
C5—C16 | 1.5042 (16) | C23—H23C | 0.9800 |
C5—C6 | 1.5267 (15) | C24—C25 | 1.500 (2) |
C6—C21 | 1.4941 (16) | C24—H24A | 0.9900 |
C6—C7 | 1.5584 (15) | C24—H24B | 0.9900 |
C7—C26 | 1.5044 (15) | C25—H25A | 0.9800 |
C8—C9 | 1.4992 (18) | C25—H25B | 0.9800 |
C8—C10 | 1.5050 (17) | C25—H25C | 0.9800 |
C9—H9A | 0.9800 | C27—C28 | 1.495 (2) |
C9—H9B | 0.9800 | C27—H27A | 0.9900 |
C9—H9C | 0.9800 | C27—H27B | 0.9900 |
C10—H10A | 0.9800 | C28—H28A | 0.9800 |
C10—H10B | 0.9800 | C28—H28B | 0.9800 |
C10—H10C | 0.9800 | C28—H28C | 0.9800 |
C12—C13 | 1.512 (2) | C29—C30 | 1.5212 (19) |
C12—H12A | 0.9900 | C29—H29A | 0.9900 |
C12—H12B | 0.9900 | C29—H29B | 0.9900 |
C13—H13A | 0.9800 | C30—H30A | 0.9800 |
C13—H13B | 0.9800 | C30—H30B | 0.9800 |
C13—H13C | 0.9800 | C30—H30C | 0.9800 |
C11—N1—C14 | 124.43 (10) | H15A—C15—H15B | 109.5 |
C11—N1—C12 | 117.64 (10) | C14—C15—H15C | 109.5 |
C14—N1—C12 | 117.32 (10) | H15A—C15—H15C | 109.5 |
C16—N2—C19 | 123.72 (10) | H15B—C15—H15C | 109.5 |
C16—N2—C17 | 116.14 (12) | O2—C16—N2 | 121.50 (11) |
C19—N2—C17 | 119.28 (12) | O2—C16—C5 | 119.45 (10) |
C16—N2—C17' | 119.1 (2) | N2—C16—C5 | 118.99 (10) |
C19—N2—C17' | 105.2 (3) | N2—C17—C18 | 110.20 (19) |
C21—N3—C22 | 124.09 (10) | N2—C17—H17A | 109.6 |
C21—N3—C24 | 118.60 (11) | C18—C17—H17A | 109.6 |
C22—N3—C24 | 117.00 (10) | N2—C17—H17B | 109.6 |
C26—N4—C29 | 125.44 (10) | C18—C17—H17B | 109.6 |
C26—N4—C27 | 116.83 (11) | H17A—C17—H17B | 108.1 |
C29—N4—C27 | 117.15 (10) | C18'—C17'—N2 | 98.9 (5) |
C11—C1—C7 | 125.11 (9) | C18'—C17'—H17C | 112.0 |
C11—C1—C2 | 121.06 (10) | N2—C17'—H17C | 112.0 |
C7—C1—C2 | 59.99 (7) | C18'—C17'—H17D | 112.0 |
C11—C1—C5 | 131.89 (9) | N2—C17'—H17D | 112.0 |
C7—C1—C5 | 90.50 (8) | H17C—C17'—H17D | 109.7 |
C2—C1—C5 | 103.96 (9) | C17'—C18'—H18D | 109.5 |
C3—C2—C7 | 110.12 (9) | C17'—C18'—H18E | 109.5 |
C3—C2—C1 | 110.08 (9) | H18D—C18'—H18E | 109.5 |
C7—C2—C1 | 59.96 (7) | C17'—C18'—H18F | 109.5 |
C3—C2—H2 | 120.6 | H18D—C18'—H18F | 109.5 |
C7—C2—H2 | 120.6 | H18E—C18'—H18F | 109.5 |
C1—C2—H2 | 120.6 | N2—C19—C20 | 112.70 (12) |
C8—C3—C4 | 129.07 (11) | N2—C19—H19A | 109.1 |
C8—C3—C2 | 129.53 (11) | C20—C19—H19A | 109.1 |
C4—C3—C2 | 101.39 (9) | N2—C19—H19B | 109.1 |
C3—C4—C5 | 110.66 (9) | C20—C19—H19B | 109.1 |
C3—C4—C6 | 109.84 (9) | H19A—C19—H19B | 107.8 |
C5—C4—C6 | 59.99 (7) | C19—C20—H20A | 109.5 |
C3—C4—H4 | 120.5 | C19—C20—H20B | 109.5 |
C5—C4—H4 | 120.5 | H20A—C20—H20B | 109.5 |
C6—C4—H4 | 120.5 | C19—C20—H20C | 109.5 |
C16—C5—C4 | 118.08 (9) | H20A—C20—H20C | 109.5 |
C16—C5—C6 | 127.69 (10) | H20B—C20—H20C | 109.5 |
C4—C5—C6 | 60.05 (7) | O3—C21—N3 | 123.29 (11) |
C16—C5—C1 | 134.13 (9) | O3—C21—C6 | 120.55 (11) |
C4—C5—C1 | 103.19 (9) | N3—C21—C6 | 116.14 (10) |
C6—C5—C1 | 89.13 (8) | N3—C22—C23 | 113.38 (11) |
C21—C6—C5 | 126.55 (10) | N3—C22—H22A | 108.9 |
C21—C6—C4 | 120.54 (9) | C23—C22—H22A | 108.9 |
C5—C6—C4 | 59.97 (7) | N3—C22—H22B | 108.9 |
C21—C6—C7 | 131.46 (9) | C23—C22—H22B | 108.9 |
C5—C6—C7 | 90.85 (8) | H22A—C22—H22B | 107.7 |
C4—C6—C7 | 104.05 (9) | C22—C23—H23A | 109.5 |
C26—C7—C1 | 130.13 (9) | C22—C23—H23B | 109.5 |
C26—C7—C2 | 118.76 (10) | H23A—C23—H23B | 109.5 |
C1—C7—C2 | 60.06 (7) | C22—C23—H23C | 109.5 |
C26—C7—C6 | 131.97 (10) | H23A—C23—H23C | 109.5 |
C1—C7—C6 | 89.52 (8) | H23B—C23—H23C | 109.5 |
C2—C7—C6 | 103.48 (8) | N3—C24—C25 | 112.33 (12) |
C3—C8—C9 | 122.46 (11) | N3—C24—H24A | 109.1 |
C3—C8—C10 | 122.65 (12) | C25—C24—H24A | 109.1 |
C9—C8—C10 | 114.88 (11) | N3—C24—H24B | 109.1 |
C8—C9—H9A | 109.5 | C25—C24—H24B | 109.1 |
C8—C9—H9B | 109.5 | H24A—C24—H24B | 107.9 |
H9A—C9—H9B | 109.5 | C24—C25—H25A | 109.5 |
C8—C9—H9C | 109.5 | C24—C25—H25B | 109.5 |
H9A—C9—H9C | 109.5 | H25A—C25—H25B | 109.5 |
H9B—C9—H9C | 109.5 | C24—C25—H25C | 109.5 |
C8—C10—H10A | 109.5 | H25A—C25—H25C | 109.5 |
C8—C10—H10B | 109.5 | H25B—C25—H25C | 109.5 |
H10A—C10—H10B | 109.5 | O4—C26—N4 | 121.23 (10) |
C8—C10—H10C | 109.5 | O4—C26—C7 | 118.83 (10) |
H10A—C10—H10C | 109.5 | N4—C26—C7 | 119.86 (10) |
H10B—C10—H10C | 109.5 | N4—C27—C28 | 112.51 (12) |
O1—C11—N1 | 122.59 (10) | N4—C27—H27A | 109.1 |
O1—C11—C1 | 120.01 (10) | C28—C27—H27A | 109.1 |
N1—C11—C1 | 117.40 (10) | N4—C27—H27B | 109.1 |
N1—C12—C13 | 113.58 (11) | C28—C27—H27B | 109.1 |
N1—C12—H12A | 108.8 | H27A—C27—H27B | 107.8 |
C13—C12—H12A | 108.9 | C27—C28—H28A | 109.5 |
N1—C12—H12B | 108.8 | C27—C28—H28B | 109.5 |
C13—C12—H12B | 108.9 | H28A—C28—H28B | 109.5 |
H12A—C12—H12B | 107.7 | C27—C28—H28C | 109.5 |
C12—C13—H13A | 109.5 | H28A—C28—H28C | 109.5 |
C12—C13—H13B | 109.5 | H28B—C28—H28C | 109.5 |
H13A—C13—H13B | 109.5 | N4—C29—C30 | 113.30 (11) |
C12—C13—H13C | 109.5 | N4—C29—H29A | 108.9 |
H13A—C13—H13C | 109.5 | C30—C29—H29A | 108.9 |
H13B—C13—H13C | 109.5 | N4—C29—H29B | 108.9 |
N1—C14—C15 | 112.55 (11) | C30—C29—H29B | 108.9 |
N1—C14—H14A | 109.1 | H29A—C29—H29B | 107.7 |
C15—C14—H14A | 109.1 | C29—C30—H30A | 109.5 |
N1—C14—H14B | 109.1 | C29—C30—H30B | 109.5 |
C15—C14—H14B | 109.1 | H30A—C30—H30B | 109.5 |
H14A—C14—H14B | 107.8 | C29—C30—H30C | 109.5 |
C14—C15—H15A | 109.5 | H30A—C30—H30C | 109.5 |
C14—C15—H15B | 109.5 | H30B—C30—H30C | 109.5 |
C11—C1—C2—C3 | 142.47 (10) | C2—C3—C8—C10 | −175.61 (11) |
C7—C1—C2—C3 | −102.22 (10) | C14—N1—C11—O1 | −171.47 (11) |
C5—C1—C2—C3 | −19.88 (11) | C12—N1—C11—O1 | −0.67 (17) |
C11—C1—C2—C7 | −115.31 (11) | C14—N1—C11—C1 | 8.96 (17) |
C5—C1—C2—C7 | 82.35 (9) | C12—N1—C11—C1 | 179.76 (10) |
C7—C2—C3—C8 | 146.13 (12) | C7—C1—C11—O1 | 20.21 (17) |
C1—C2—C3—C8 | −149.58 (11) | C2—C1—C11—O1 | 93.33 (13) |
C7—C2—C3—C4 | −32.58 (11) | C5—C1—C11—O1 | −109.96 (14) |
C1—C2—C3—C4 | 31.71 (11) | C7—C1—C11—N1 | −160.21 (11) |
C8—C3—C4—C5 | 149.18 (12) | C2—C1—C11—N1 | −87.08 (13) |
C2—C3—C4—C5 | −32.10 (11) | C5—C1—C11—N1 | 69.63 (16) |
C8—C3—C4—C6 | −146.43 (12) | C11—N1—C12—C13 | −81.84 (15) |
C2—C3—C4—C6 | 32.29 (11) | C14—N1—C12—C13 | 89.63 (14) |
C3—C4—C5—C16 | −138.90 (10) | C11—N1—C14—C15 | −113.37 (13) |
C6—C4—C5—C16 | 119.50 (11) | C12—N1—C14—C15 | 75.81 (14) |
C3—C4—C5—C6 | 101.60 (10) | C19—N2—C16—O2 | −161.87 (12) |
C3—C4—C5—C1 | 20.41 (11) | C17—N2—C16—O2 | 7.4 (2) |
C6—C4—C5—C1 | −81.19 (9) | C17'—N2—C16—O2 | −24.9 (4) |
C11—C1—C5—C16 | −5.5 (2) | C19—N2—C16—C5 | 20.79 (19) |
C7—C1—C5—C16 | −146.85 (13) | C17—N2—C16—C5 | −169.94 (14) |
C2—C1—C5—C16 | 154.03 (12) | C17'—N2—C16—C5 | 157.8 (4) |
C11—C1—C5—C4 | −159.80 (11) | C4—C5—C16—O2 | 11.32 (16) |
C7—C1—C5—C4 | 58.89 (9) | C6—C5—C16—O2 | 83.68 (15) |
C2—C1—C5—C4 | −0.23 (10) | C1—C5—C16—O2 | −140.05 (13) |
C11—C1—C5—C6 | 141.29 (12) | C4—C5—C16—N2 | −171.29 (11) |
C7—C1—C5—C6 | −0.01 (8) | C6—C5—C16—N2 | −98.92 (14) |
C2—C1—C5—C6 | −59.14 (9) | C1—C5—C16—N2 | 37.35 (19) |
C16—C5—C6—C21 | 3.62 (18) | C16—N2—C17—C18 | −99.26 (19) |
C4—C5—C6—C21 | 107.58 (12) | C19—N2—C17—C18 | 70.5 (2) |
C1—C5—C6—C21 | −146.63 (11) | C17'—N2—C17—C18 | 4.2 (5) |
C16—C5—C6—C4 | −103.96 (12) | C16—N2—C17'—C18' | 98.6 (4) |
C1—C5—C6—C4 | 105.79 (9) | C19—N2—C17'—C18' | −117.4 (4) |
C16—C5—C6—C7 | 150.26 (11) | C17—N2—C17'—C18' | 6.7 (3) |
C4—C5—C6—C7 | −105.78 (9) | C16—N2—C19—C20 | −136.44 (14) |
C1—C5—C6—C7 | 0.01 (8) | C17—N2—C19—C20 | 54.61 (19) |
C3—C4—C6—C21 | 139.78 (10) | C17'—N2—C19—C20 | 81.7 (3) |
C5—C4—C6—C21 | −117.23 (12) | C22—N3—C21—O3 | −175.04 (11) |
C3—C4—C6—C5 | −102.99 (10) | C24—N3—C21—O3 | −1.60 (18) |
C3—C4—C6—C7 | −20.29 (11) | C22—N3—C21—C6 | 3.30 (17) |
C5—C4—C6—C7 | 82.70 (9) | C24—N3—C21—C6 | 176.74 (10) |
C11—C1—C7—C26 | 4.88 (19) | C5—C6—C21—O3 | 16.84 (17) |
C2—C1—C7—C26 | −103.92 (13) | C4—C6—C21—O3 | 90.22 (13) |
C5—C1—C7—C26 | 150.20 (12) | C7—C6—C21—O3 | −115.97 (14) |
C11—C1—C7—C2 | 108.80 (12) | C5—C6—C21—N3 | −161.55 (11) |
C5—C1—C7—C2 | −105.88 (9) | C4—C6—C21—N3 | −88.17 (13) |
C11—C1—C7—C6 | −145.31 (11) | C7—C6—C21—N3 | 65.64 (16) |
C2—C1—C7—C6 | 105.89 (8) | C21—N3—C22—C23 | 98.31 (14) |
C5—C1—C7—C6 | 0.01 (8) | C24—N3—C22—C23 | −75.22 (14) |
C3—C2—C7—C26 | −135.69 (10) | C21—N3—C24—C25 | 99.69 (15) |
C1—C2—C7—C26 | 122.16 (11) | C22—N3—C24—C25 | −86.41 (16) |
C3—C2—C7—C1 | 102.15 (10) | C29—N4—C26—O4 | −166.04 (11) |
C3—C2—C7—C6 | 20.66 (11) | C27—N4—C26—O4 | 4.97 (17) |
C1—C2—C7—C6 | −81.49 (9) | C29—N4—C26—C7 | 17.24 (17) |
C21—C6—C7—C26 | −5.4 (2) | C27—N4—C26—C7 | −171.75 (10) |
C5—C6—C7—C26 | −149.26 (12) | C1—C7—C26—O4 | 86.00 (15) |
C4—C6—C7—C26 | 151.55 (11) | C2—C7—C26—O4 | 12.39 (15) |
C21—C6—C7—C1 | 143.87 (12) | C6—C7—C26—O4 | −135.97 (12) |
C5—C6—C7—C1 | −0.02 (8) | C1—C7—C26—N4 | −97.21 (14) |
C4—C6—C7—C1 | −59.20 (9) | C2—C7—C26—N4 | −170.82 (10) |
C21—C6—C7—C2 | −157.15 (11) | C6—C7—C26—N4 | 40.83 (17) |
C5—C6—C7—C2 | 58.97 (9) | C26—N4—C27—C28 | 86.32 (16) |
C4—C6—C7—C2 | −0.22 (10) | C29—N4—C27—C28 | −101.91 (15) |
C4—C3—C8—C9 | −177.87 (11) | C26—N4—C29—C30 | 104.11 (14) |
C2—C3—C8—C9 | 3.75 (19) | C27—N4—C29—C30 | −66.87 (15) |
C4—C3—C8—C10 | 2.77 (19) |
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O1i | 0.98 | 2.66 | 3.2511 (16) | 119 |
C2—H2···O4i | 1.00 | 2.41 | 3.2105 (14) | 137 |
C15—H15B···O2ii | 0.98 | 2.62 | 3.3651 (18) | 133 |
C24—H24B···O2iii | 0.99 | 2.55 | 3.3575 (16) | 138 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+1, −y+1, −z. |