Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803013709/bt6290sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803013709/bt6290Isup2.hkl |
CCDC reference: 221672
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 | F(000) = 1152 |
Mr = 528.72 | Dx = 1.142 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 10.7945 (12) Å | Cell parameters from 4910 reflections |
b = 25.449 (3) Å | θ = 2.2–28° |
c = 11.6710 (12) Å | µ = 0.08 mm−1 |
β = 106.353 (3)° | T = 133 K |
V = 3076.4 (6) Å3 | Prism, colourless |
Z = 4 | 0.44 × 0.27 × 0.22 mm |
Bruker SMART 1000 CCD diffractometer | 4102 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.051 |
Graphite monochromator | θmax = 26.4°, θmin = 2.0° |
Detector resolution: 8.192 pixels mm-1 | h = −13→13 |
ω scans | k = −31→25 |
19202 measured reflections | l = −14→13 |
6300 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) = 0.114 | H-atom parameters constrained |
S = 0.94 | w = 1/[σ2(Fo2) + (0.062P)2] where P = (Fo2 + 2Fc2)/3 |
6300 reflections | (Δ/σ)max = 0.001 |
353 parameters | Δρmax = 0.29 e Å−3 |
0 restraints | Δρmin = −0.19 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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.0405 (0.0030) x + 15.8337 (0.0086) y + 2.7059 (0.0045) z = 15.5432 (0.0038) * 0.0790 (0.0008) C11 * -0.0781 (0.0008) C16 * 0.0781 (0.0008) C21 * -0.0790 (0.0008) C26 0.8890 (0.0020) O1 - 1.0521 (0.0017) O2 0.8748 (0.0019) O3 - 1.0146 (0.0018) O4 Rms deviation of fitted atoms = 0.0785 |
x | y | z | Uiso*/Ueq | ||
O1 | 0.79816 (11) | 0.66733 (5) | 0.09104 (9) | 0.0359 (3) | |
O2 | 0.75937 (10) | 0.51322 (4) | 0.37644 (10) | 0.0362 (3) | |
O3 | 0.66659 (10) | 0.62720 (5) | 0.66299 (9) | 0.0366 (3) | |
O4 | 0.42995 (10) | 0.68820 (5) | 0.22351 (9) | 0.0326 (3) | |
N1 | 0.66646 (12) | 0.59666 (5) | 0.06782 (11) | 0.0297 (3) | |
N2 | 0.94430 (11) | 0.53210 (5) | 0.33016 (11) | 0.0271 (3) | |
N3 | 0.48350 (11) | 0.60232 (5) | 0.52538 (11) | 0.0271 (3) | |
N4 | 0.44752 (13) | 0.74008 (6) | 0.38489 (12) | 0.0389 (4) | |
C1 | 0.73255 (13) | 0.68912 (6) | 0.32409 (13) | 0.0232 (3) | |
H1 | 0.7278 | 0.7219 | 0.2759 | 0.028* | |
C2 | 0.75545 (13) | 0.63725 (6) | 0.26518 (13) | 0.0227 (3) | |
C3 | 0.80098 (12) | 0.60263 (6) | 0.35372 (12) | 0.0212 (3) | |
C4 | 0.80330 (13) | 0.63064 (6) | 0.47131 (12) | 0.0217 (3) | |
H4 | 0.8578 | 0.6145 | 0.5469 | 0.026* | |
C5 | 0.66173 (13) | 0.64309 (6) | 0.46530 (12) | 0.0220 (3) | |
C6 | 0.62009 (13) | 0.67880 (6) | 0.37921 (12) | 0.0223 (3) | |
C7 | 0.84278 (13) | 0.68522 (6) | 0.43928 (12) | 0.0224 (3) | |
C8 | 0.93647 (14) | 0.71763 (6) | 0.49500 (13) | 0.0272 (4) | |
C9 | 1.03525 (15) | 0.70210 (7) | 0.60898 (15) | 0.0352 (4) | |
H9A | 1.0206 | 0.7221 | 0.6757 | 0.042* | |
H9B | 1.1220 | 0.7096 | 0.6023 | 0.042* | |
H9C | 1.0275 | 0.6644 | 0.6232 | 0.042* | |
C10 | 0.94805 (17) | 0.77257 (7) | 0.45172 (16) | 0.0369 (4) | |
H10A | 0.8897 | 0.7768 | 0.3711 | 0.044* | |
H10B | 1.0371 | 0.7789 | 0.4502 | 0.044* | |
H10C | 0.9249 | 0.7978 | 0.5057 | 0.044* | |
C11 | 0.74030 (14) | 0.63450 (6) | 0.13440 (13) | 0.0258 (3) | |
C12 | 0.57984 (15) | 0.56158 (7) | 0.10810 (14) | 0.0333 (4) | |
H12A | 0.6051 | 0.5613 | 0.1965 | 0.040* | |
H12B | 0.5899 | 0.5254 | 0.0808 | 0.040* | |
C13 | 0.43891 (15) | 0.57763 (8) | 0.06197 (16) | 0.0403 (4) | |
H13A | 0.4268 | 0.6122 | 0.0942 | 0.048* | |
H13B | 0.3849 | 0.5517 | 0.0874 | 0.048* | |
H13C | 0.4141 | 0.5793 | −0.0254 | 0.048* | |
C14 | 0.66111 (16) | 0.59381 (8) | −0.05969 (14) | 0.0372 (4) | |
H14A | 0.6589 | 0.6299 | −0.0917 | 0.045* | |
H14B | 0.5802 | 0.5760 | −0.1038 | 0.045* | |
C15 | 0.77390 (17) | 0.56487 (8) | −0.08165 (14) | 0.0420 (4) | |
H15A | 0.8533 | 0.5849 | −0.0476 | 0.050* | |
H15B | 0.7603 | 0.5607 | −0.1678 | 0.050* | |
H15C | 0.7815 | 0.5302 | −0.0439 | 0.050* | |
C16 | 0.83304 (13) | 0.54597 (6) | 0.35305 (12) | 0.0228 (3) | |
C17 | 0.97370 (16) | 0.47609 (7) | 0.32691 (15) | 0.0367 (4) | |
H17A | 0.9509 | 0.4582 | 0.3935 | 0.044* | |
H17B | 1.0677 | 0.4718 | 0.3394 | 0.044* | |
C18 | 0.9026 (2) | 0.44980 (8) | 0.21083 (17) | 0.0545 (5) | |
H18A | 0.8093 | 0.4527 | 0.1993 | 0.065* | |
H18B | 0.9271 | 0.4126 | 0.2136 | 0.065* | |
H18C | 0.9252 | 0.4671 | 0.1444 | 0.065* | |
C19 | 1.04566 (14) | 0.56986 (7) | 0.32538 (15) | 0.0354 (4) | |
H19A | 1.1274 | 0.5593 | 0.3841 | 0.042* | |
H19B | 1.0217 | 0.6049 | 0.3491 | 0.042* | |
C20 | 1.06780 (17) | 0.57395 (9) | 0.20379 (16) | 0.0494 (5) | |
H20A | 1.0864 | 0.5390 | 0.1775 | 0.059* | |
H20B | 1.1411 | 0.5973 | 0.2081 | 0.059* | |
H20C | 0.9903 | 0.5882 | 0.1468 | 0.059* | |
C21 | 0.60349 (14) | 0.62291 (6) | 0.55785 (13) | 0.0234 (3) | |
C22 | 0.42408 (16) | 0.59024 (7) | 0.62121 (14) | 0.0340 (4) | |
H22A | 0.4898 | 0.5748 | 0.6898 | 0.041* | |
H22B | 0.3547 | 0.5640 | 0.5922 | 0.041* | |
C23 | 0.3686 (2) | 0.63881 (9) | 0.6614 (2) | 0.0629 (6) | |
H23A | 0.4372 | 0.6648 | 0.6905 | 0.076* | |
H23B | 0.3307 | 0.6297 | 0.7259 | 0.076* | |
H23C | 0.3017 | 0.6536 | 0.5941 | 0.076* | |
C24 | 0.40765 (15) | 0.59014 (7) | 0.40285 (14) | 0.0305 (4) | |
H24A | 0.4483 | 0.6075 | 0.3466 | 0.037* | |
H24B | 0.3200 | 0.6050 | 0.3891 | 0.037* | |
C25 | 0.39613 (17) | 0.53208 (7) | 0.37571 (15) | 0.0400 (4) | |
H25A | 0.4819 | 0.5176 | 0.3820 | 0.048* | |
H25B | 0.3400 | 0.5266 | 0.2946 | 0.048* | |
H25C | 0.3590 | 0.5143 | 0.4329 | 0.048* | |
C26 | 0.49095 (14) | 0.70284 (6) | 0.32486 (13) | 0.0264 (3) | |
C27 | 0.52281 (19) | 0.76161 (8) | 0.50031 (16) | 0.0461 (5) | |
H27A | 0.5818 | 0.7341 | 0.5451 | 0.055* | |
H27B | 0.4634 | 0.7715 | 0.5476 | 0.055* | |
C28 | 0.6009 (2) | 0.80920 (9) | 0.48557 (19) | 0.0650 (6) | |
H28A | 0.6586 | 0.7997 | 0.4373 | 0.078* | |
H28B | 0.6523 | 0.8214 | 0.5643 | 0.078* | |
H28C | 0.5425 | 0.8373 | 0.4456 | 0.078* | |
C29 | 0.32216 (18) | 0.76484 (9) | 0.32497 (18) | 0.0557 (6) | |
H29A | 0.3160 | 0.7704 | 0.2396 | 0.067* | |
H29B | 0.3172 | 0.7996 | 0.3615 | 0.067* | |
C30 | 0.21109 (19) | 0.73157 (12) | 0.3348 (2) | 0.0785 (9) | |
H30A | 0.2147 | 0.6974 | 0.2972 | 0.094* | |
H30B | 0.1297 | 0.7492 | 0.2945 | 0.094* | |
H30C | 0.2162 | 0.7264 | 0.4192 | 0.094* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0428 (7) | 0.0354 (7) | 0.0336 (7) | −0.0058 (6) | 0.0177 (5) | 0.0043 (5) |
O2 | 0.0339 (6) | 0.0246 (7) | 0.0550 (8) | −0.0029 (5) | 0.0204 (6) | 0.0046 (5) |
O3 | 0.0336 (6) | 0.0517 (8) | 0.0232 (6) | −0.0091 (5) | 0.0058 (5) | 0.0009 (5) |
O4 | 0.0290 (6) | 0.0393 (7) | 0.0265 (6) | 0.0062 (5) | 0.0028 (5) | 0.0009 (5) |
N1 | 0.0307 (7) | 0.0355 (8) | 0.0223 (7) | −0.0043 (6) | 0.0066 (6) | −0.0040 (6) |
N2 | 0.0217 (6) | 0.0244 (7) | 0.0352 (7) | 0.0042 (5) | 0.0079 (6) | 0.0007 (6) |
N3 | 0.0225 (6) | 0.0345 (8) | 0.0256 (7) | −0.0034 (6) | 0.0089 (5) | −0.0001 (6) |
N4 | 0.0368 (8) | 0.0437 (9) | 0.0327 (8) | 0.0201 (7) | 0.0041 (6) | −0.0038 (7) |
C1 | 0.0250 (7) | 0.0204 (8) | 0.0248 (8) | 0.0008 (6) | 0.0081 (6) | 0.0028 (6) |
C2 | 0.0188 (7) | 0.0222 (8) | 0.0277 (8) | −0.0028 (6) | 0.0077 (6) | −0.0004 (6) |
C3 | 0.0158 (7) | 0.0219 (8) | 0.0267 (8) | −0.0022 (6) | 0.0071 (6) | −0.0002 (6) |
C4 | 0.0183 (7) | 0.0218 (8) | 0.0239 (8) | 0.0015 (6) | 0.0043 (6) | 0.0012 (6) |
C5 | 0.0213 (7) | 0.0223 (8) | 0.0223 (8) | 0.0003 (6) | 0.0062 (6) | −0.0037 (6) |
C6 | 0.0217 (7) | 0.0221 (8) | 0.0229 (8) | 0.0012 (6) | 0.0057 (6) | −0.0031 (6) |
C7 | 0.0225 (7) | 0.0211 (8) | 0.0251 (8) | 0.0020 (6) | 0.0094 (6) | −0.0011 (6) |
C8 | 0.0270 (8) | 0.0264 (9) | 0.0307 (8) | −0.0017 (7) | 0.0123 (7) | −0.0056 (7) |
C9 | 0.0266 (8) | 0.0356 (10) | 0.0409 (10) | −0.0059 (7) | 0.0053 (7) | −0.0103 (8) |
C10 | 0.0423 (10) | 0.0274 (10) | 0.0454 (10) | −0.0090 (8) | 0.0194 (8) | −0.0071 (8) |
C11 | 0.0251 (8) | 0.0255 (9) | 0.0274 (8) | 0.0045 (7) | 0.0084 (7) | 0.0025 (7) |
C12 | 0.0357 (9) | 0.0326 (10) | 0.0293 (9) | −0.0077 (8) | 0.0055 (7) | −0.0038 (7) |
C13 | 0.0353 (9) | 0.0432 (12) | 0.0417 (10) | −0.0060 (8) | 0.0096 (8) | −0.0067 (8) |
C14 | 0.0397 (9) | 0.0470 (11) | 0.0230 (8) | 0.0021 (8) | 0.0058 (7) | −0.0034 (8) |
C15 | 0.0508 (11) | 0.0492 (12) | 0.0268 (9) | 0.0068 (9) | 0.0121 (8) | −0.0031 (8) |
C16 | 0.0215 (7) | 0.0227 (8) | 0.0230 (8) | −0.0001 (6) | 0.0044 (6) | 0.0002 (6) |
C17 | 0.0372 (9) | 0.0304 (10) | 0.0435 (10) | 0.0130 (8) | 0.0132 (8) | 0.0033 (8) |
C18 | 0.0782 (14) | 0.0325 (11) | 0.0533 (12) | 0.0103 (10) | 0.0191 (11) | −0.0068 (9) |
C19 | 0.0210 (8) | 0.0401 (11) | 0.0453 (10) | −0.0015 (7) | 0.0097 (7) | 0.0030 (8) |
C20 | 0.0284 (9) | 0.0698 (15) | 0.0486 (11) | −0.0012 (9) | 0.0086 (8) | 0.0136 (10) |
C21 | 0.0241 (7) | 0.0234 (9) | 0.0232 (8) | 0.0010 (6) | 0.0074 (6) | −0.0004 (6) |
C22 | 0.0313 (9) | 0.0416 (11) | 0.0335 (9) | −0.0060 (8) | 0.0166 (7) | 0.0001 (8) |
C23 | 0.0735 (14) | 0.0609 (15) | 0.0751 (15) | 0.0150 (12) | 0.0548 (13) | 0.0072 (12) |
C24 | 0.0246 (8) | 0.0354 (10) | 0.0289 (8) | −0.0019 (7) | 0.0032 (7) | 0.0004 (7) |
C25 | 0.0381 (9) | 0.0399 (11) | 0.0363 (10) | 0.0001 (8) | 0.0012 (8) | −0.0028 (8) |
C26 | 0.0256 (8) | 0.0280 (9) | 0.0256 (8) | 0.0055 (7) | 0.0073 (7) | 0.0035 (7) |
C27 | 0.0558 (11) | 0.0452 (12) | 0.0338 (10) | 0.0227 (10) | 0.0070 (9) | −0.0084 (8) |
C28 | 0.0782 (15) | 0.0553 (15) | 0.0560 (13) | 0.0038 (13) | 0.0102 (12) | −0.0177 (11) |
C29 | 0.0505 (12) | 0.0653 (15) | 0.0458 (12) | 0.0386 (11) | 0.0044 (9) | −0.0044 (10) |
C30 | 0.0384 (11) | 0.147 (3) | 0.0545 (14) | 0.0421 (14) | 0.0200 (10) | 0.0244 (14) |
O1—C11 | 1.2339 (18) | C13—H13C | 0.9800 |
O2—C16 | 1.2345 (17) | C14—C15 | 1.505 (2) |
O3—C21 | 1.2292 (16) | C14—H14A | 0.9900 |
O4—C26 | 1.2382 (17) | C14—H14B | 0.9900 |
N1—C11 | 1.348 (2) | C15—H15A | 0.9800 |
N1—C12 | 1.463 (2) | C15—H15B | 0.9800 |
N1—C14 | 1.475 (2) | C15—H15C | 0.9800 |
N2—C16 | 1.3488 (18) | C17—C18 | 1.512 (3) |
N2—C17 | 1.463 (2) | C17—H17A | 0.9900 |
N2—C19 | 1.469 (2) | C17—H17B | 0.9900 |
N3—C21 | 1.3487 (19) | C18—H18A | 0.9800 |
N3—C24 | 1.4670 (19) | C18—H18B | 0.9800 |
N3—C22 | 1.4701 (19) | C18—H18C | 0.9800 |
N4—C26 | 1.339 (2) | C19—C20 | 1.507 (2) |
N4—C27 | 1.469 (2) | C19—H19A | 0.9900 |
N4—C29 | 1.478 (2) | C19—H19B | 0.9900 |
C1—C7 | 1.527 (2) | C20—H20A | 0.9800 |
C1—C2 | 1.540 (2) | C20—H20B | 0.9800 |
C1—C6 | 1.548 (2) | C20—H20C | 0.9800 |
C1—H1 | 1.0000 | C22—C23 | 1.505 (3) |
C2—C3 | 1.342 (2) | C22—H22A | 0.9900 |
C2—C11 | 1.490 (2) | C22—H22B | 0.9900 |
C3—C16 | 1.483 (2) | C23—H23A | 0.9800 |
C3—C4 | 1.541 (2) | C23—H23B | 0.9800 |
C4—C7 | 1.530 (2) | C23—H23C | 0.9800 |
C4—C5 | 1.5428 (19) | C24—C25 | 1.509 (2) |
C4—H4 | 1.0000 | C24—H24A | 0.9900 |
C5—C6 | 1.335 (2) | C24—H24B | 0.9900 |
C5—C21 | 1.486 (2) | C25—H25A | 0.9800 |
C6—C26 | 1.491 (2) | C25—H25B | 0.9800 |
C7—C8 | 1.325 (2) | C25—H25C | 0.9800 |
C8—C10 | 1.504 (2) | C27—C28 | 1.513 (3) |
C8—C9 | 1.505 (2) | C27—H27A | 0.9900 |
C9—H9A | 0.9800 | C27—H27B | 0.9900 |
C9—H9B | 0.9800 | C28—H28A | 0.9800 |
C9—H9C | 0.9800 | C28—H28B | 0.9800 |
C10—H10A | 0.9800 | C28—H28C | 0.9800 |
C10—H10B | 0.9800 | C29—C30 | 1.498 (3) |
C10—H10C | 0.9800 | C29—H29A | 0.9900 |
C12—C13 | 1.520 (2) | C29—H29B | 0.9900 |
C12—H12A | 0.9900 | C30—H30A | 0.9800 |
C12—H12B | 0.9900 | C30—H30B | 0.9800 |
C13—H13A | 0.9800 | C30—H30C | 0.9800 |
C13—H13B | 0.9800 | ||
C11—N1—C12 | 125.33 (12) | O2—C16—N2 | 122.14 (14) |
C11—N1—C14 | 117.74 (13) | O2—C16—C3 | 119.29 (13) |
C12—N1—C14 | 116.58 (13) | N2—C16—C3 | 118.53 (13) |
C16—N2—C17 | 118.16 (13) | N2—C17—C18 | 113.27 (14) |
C16—N2—C19 | 123.40 (13) | N2—C17—H17A | 108.9 |
C17—N2—C19 | 117.84 (12) | C18—C17—H17A | 108.9 |
C21—N3—C24 | 125.76 (12) | N2—C17—H17B | 108.9 |
C21—N3—C22 | 117.24 (12) | C18—C17—H17B | 108.9 |
C24—N3—C22 | 117.00 (12) | H17A—C17—H17B | 107.7 |
C26—N4—C27 | 123.96 (13) | C17—C18—H18A | 109.5 |
C26—N4—C29 | 117.57 (14) | C17—C18—H18B | 109.5 |
C27—N4—C29 | 118.12 (14) | H18A—C18—H18B | 109.5 |
C7—C1—C2 | 98.86 (11) | C17—C18—H18C | 109.5 |
C7—C1—C6 | 97.53 (11) | H18A—C18—H18C | 109.5 |
C2—C1—C6 | 106.45 (12) | H18B—C18—H18C | 109.5 |
C7—C1—H1 | 117.0 | N2—C19—C20 | 113.45 (14) |
C2—C1—H1 | 117.0 | N2—C19—H19A | 108.9 |
C6—C1—H1 | 117.0 | C20—C19—H19A | 108.9 |
C3—C2—C11 | 131.97 (14) | N2—C19—H19B | 108.9 |
C3—C2—C1 | 106.81 (12) | C20—C19—H19B | 108.9 |
C11—C2—C1 | 120.83 (13) | H19A—C19—H19B | 107.7 |
C2—C3—C16 | 132.06 (13) | C19—C20—H20A | 109.5 |
C2—C3—C4 | 107.02 (13) | C19—C20—H20B | 109.5 |
C16—C3—C4 | 120.62 (12) | H20A—C20—H20B | 109.5 |
C7—C4—C3 | 97.95 (11) | C19—C20—H20C | 109.5 |
C7—C4—C5 | 98.22 (11) | H20A—C20—H20C | 109.5 |
C3—C4—C5 | 106.68 (11) | H20B—C20—H20C | 109.5 |
C7—C4—H4 | 117.0 | O3—C21—N3 | 122.24 (13) |
C3—C4—H4 | 117.0 | O3—C21—C5 | 117.77 (13) |
C5—C4—H4 | 117.0 | N3—C21—C5 | 119.95 (13) |
C6—C5—C21 | 131.34 (13) | N3—C22—C23 | 111.27 (15) |
C6—C5—C4 | 107.05 (12) | N3—C22—H22A | 109.4 |
C21—C5—C4 | 120.82 (12) | C23—C22—H22A | 109.4 |
C5—C6—C26 | 132.52 (13) | N3—C22—H22B | 109.4 |
C5—C6—C1 | 106.91 (12) | C23—C22—H22B | 109.4 |
C26—C6—C1 | 120.16 (12) | H22A—C22—H22B | 108.0 |
C8—C7—C1 | 133.59 (14) | C22—C23—H23A | 109.5 |
C8—C7—C4 | 132.21 (14) | C22—C23—H23B | 109.5 |
C1—C7—C4 | 94.16 (11) | H23A—C23—H23B | 109.5 |
C7—C8—C10 | 122.55 (15) | C22—C23—H23C | 109.5 |
C7—C8—C9 | 121.55 (15) | H23A—C23—H23C | 109.5 |
C10—C8—C9 | 115.85 (14) | H23B—C23—H23C | 109.5 |
C8—C9—H9A | 109.5 | N3—C24—C25 | 113.70 (13) |
C8—C9—H9B | 109.5 | N3—C24—H24A | 108.8 |
H9A—C9—H9B | 109.5 | C25—C24—H24A | 108.8 |
C8—C9—H9C | 109.5 | N3—C24—H24B | 108.8 |
H9A—C9—H9C | 109.5 | C25—C24—H24B | 108.8 |
H9B—C9—H9C | 109.5 | H24A—C24—H24B | 107.7 |
C8—C10—H10A | 109.5 | C24—C25—H25A | 109.5 |
C8—C10—H10B | 109.5 | C24—C25—H25B | 109.5 |
H10A—C10—H10B | 109.5 | H25A—C25—H25B | 109.5 |
C8—C10—H10C | 109.5 | C24—C25—H25C | 109.5 |
H10A—C10—H10C | 109.5 | H25A—C25—H25C | 109.5 |
H10B—C10—H10C | 109.5 | H25B—C25—H25C | 109.5 |
O1—C11—N1 | 122.19 (14) | O4—C26—N4 | 122.84 (14) |
O1—C11—C2 | 117.77 (14) | O4—C26—C6 | 117.71 (13) |
N1—C11—C2 | 120.03 (13) | N4—C26—C6 | 119.41 (13) |
N1—C12—C13 | 112.89 (14) | N4—C27—C28 | 112.11 (15) |
N1—C12—H12A | 109.0 | N4—C27—H27A | 109.2 |
C13—C12—H12A | 109.0 | C28—C27—H27A | 109.2 |
N1—C12—H12B | 109.0 | N4—C27—H27B | 109.2 |
C13—C12—H12B | 109.0 | C28—C27—H27B | 109.2 |
H12A—C12—H12B | 107.8 | H27A—C27—H27B | 107.9 |
C12—C13—H13A | 109.5 | C27—C28—H28A | 109.5 |
C12—C13—H13B | 109.5 | C27—C28—H28B | 109.5 |
H13A—C13—H13B | 109.5 | H28A—C28—H28B | 109.5 |
C12—C13—H13C | 109.5 | C27—C28—H28C | 109.5 |
H13A—C13—H13C | 109.5 | H28A—C28—H28C | 109.5 |
H13B—C13—H13C | 109.5 | H28B—C28—H28C | 109.5 |
N1—C14—C15 | 113.08 (13) | N4—C29—C30 | 111.62 (18) |
N1—C14—H14A | 109.0 | N4—C29—H29A | 109.3 |
C15—C14—H14A | 109.0 | C30—C29—H29A | 109.3 |
N1—C14—H14B | 109.0 | N4—C29—H29B | 109.3 |
C15—C14—H14B | 109.0 | C30—C29—H29B | 109.3 |
H14A—C14—H14B | 107.8 | H29A—C29—H29B | 108.0 |
C14—C15—H15A | 109.5 | C29—C30—H30A | 109.5 |
C14—C15—H15B | 109.5 | C29—C30—H30B | 109.5 |
H15A—C15—H15B | 109.5 | H30A—C30—H30B | 109.5 |
C14—C15—H15C | 109.5 | C29—C30—H30C | 109.5 |
H15A—C15—H15C | 109.5 | H30A—C30—H30C | 109.5 |
H15B—C15—H15C | 109.5 | H30B—C30—H30C | 109.5 |
C7—C1—C2—C3 | 33.25 (13) | C3—C2—C11—N1 | 59.1 (2) |
C6—C1—C2—C3 | −67.37 (14) | C1—C2—C11—N1 | −129.20 (15) |
C7—C1—C2—C11 | −140.34 (13) | C11—N1—C12—C13 | 102.11 (17) |
C6—C1—C2—C11 | 119.04 (14) | C14—N1—C12—C13 | −70.93 (18) |
C11—C2—C3—C16 | −11.7 (3) | C11—N1—C14—C15 | 82.23 (19) |
C1—C2—C3—C16 | 175.70 (14) | C12—N1—C14—C15 | −104.18 (17) |
C11—C2—C3—C4 | 174.84 (14) | C17—N2—C16—O2 | 3.4 (2) |
C1—C2—C3—C4 | 2.25 (14) | C19—N2—C16—O2 | −167.55 (14) |
C2—C3—C4—C7 | −36.81 (13) | C17—N2—C16—C3 | −178.59 (12) |
C16—C3—C4—C7 | 148.84 (12) | C19—N2—C16—C3 | 10.5 (2) |
C2—C3—C4—C5 | 64.29 (14) | C2—C3—C16—O2 | −104.94 (19) |
C16—C3—C4—C5 | −110.06 (14) | C4—C3—C16—O2 | 67.78 (18) |
C7—C4—C5—C6 | 33.85 (14) | C2—C3—C16—N2 | 77.0 (2) |
C3—C4—C5—C6 | −67.05 (15) | C4—C3—C16—N2 | −110.30 (15) |
C7—C4—C5—C21 | −137.05 (13) | C16—N2—C17—C18 | 79.40 (19) |
C3—C4—C5—C21 | 122.05 (14) | C19—N2—C17—C18 | −109.16 (17) |
C21—C5—C6—C26 | −16.1 (3) | C16—N2—C19—C20 | −115.96 (17) |
C4—C5—C6—C26 | 174.27 (15) | C17—N2—C19—C20 | 73.08 (18) |
C21—C5—C6—C1 | 171.43 (14) | C24—N3—C21—O3 | −172.46 (14) |
C4—C5—C6—C1 | 1.84 (15) | C22—N3—C21—O3 | 6.5 (2) |
C7—C1—C6—C5 | −36.90 (14) | C24—N3—C21—C5 | 9.8 (2) |
C2—C1—C6—C5 | 64.70 (14) | C22—N3—C21—C5 | −171.26 (13) |
C7—C1—C6—C26 | 149.55 (13) | C6—C5—C21—O3 | −122.55 (18) |
C2—C1—C6—C26 | −108.85 (15) | C4—C5—C21—O3 | 45.8 (2) |
C2—C1—C7—C8 | 128.98 (17) | C6—C5—C21—N3 | 55.3 (2) |
C6—C1—C7—C8 | −122.97 (17) | C4—C5—C21—N3 | −136.28 (15) |
C2—C1—C7—C4 | −53.26 (11) | C21—N3—C22—C23 | 80.44 (19) |
C6—C1—C7—C4 | 54.78 (12) | C24—N3—C22—C23 | −100.47 (18) |
C3—C4—C7—C8 | −127.96 (16) | C21—N3—C24—C25 | 107.24 (18) |
C5—C4—C7—C8 | 123.80 (16) | C22—N3—C24—C25 | −71.75 (18) |
C3—C4—C7—C1 | 54.23 (11) | C27—N4—C26—O4 | −174.17 (16) |
C5—C4—C7—C1 | −54.01 (11) | C29—N4—C26—O4 | −1.1 (2) |
C1—C7—C8—C10 | 3.7 (3) | C27—N4—C26—C6 | 3.7 (2) |
C4—C7—C8—C10 | −173.26 (14) | C29—N4—C26—C6 | 176.80 (16) |
C1—C7—C8—C9 | −178.73 (14) | C5—C6—C26—O4 | −105.61 (19) |
C4—C7—C8—C9 | 4.3 (2) | C1—C6—C26—O4 | 66.01 (19) |
C12—N1—C11—O1 | −170.13 (14) | C5—C6—C26—N4 | 76.4 (2) |
C14—N1—C11—O1 | 2.8 (2) | C1—C6—C26—N4 | −111.95 (16) |
C12—N1—C11—C2 | 10.6 (2) | C26—N4—C27—C28 | 90.6 (2) |
C14—N1—C11—C2 | −176.41 (13) | C29—N4—C27—C28 | −82.5 (2) |
C3—C2—C11—O1 | −120.22 (18) | C26—N4—C29—C30 | 81.3 (2) |
C1—C2—C11—O1 | 51.52 (19) | C27—N4—C29—C30 | −105.2 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C27—H27B···O1i | 0.99 | 2.52 | 3.423 (2) | 151 |
C22—H22B···O2ii | 0.99 | 2.40 | 3.299 (2) | 151 |
C15—H15B···O3iii | 0.98 | 2.58 | 3.286 (2) | 129 |
C9—H9A···O4iv | 0.98 | 2.61 | 3.425 (2) | 141 |
C10—H10C···O4iv | 0.98 | 2.55 | 3.383 (2) | 143 |
Symmetry codes: (i) x−1/2, −y+3/2, z+1/2; (ii) −x+1, −y+1, −z+1; (iii) x, y, z−1; (iv) x+1/2, −y+3/2, z+1/2. |