Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806051014/er2023sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806051014/er2023Isup2.hkl |
CCDC reference: 633684
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 2000); software used to prepare material for publication: SHELXL97.
C18H16N4O4 | F(000) = 1472 |
Mr = 352.35 | Dx = 1.409 Mg m−3 |
Monoclinic, P21/c | Melting point = 472.4–472.8 K |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4387 (13) Å | Cell parameters from 3138 reflections |
b = 36.870 (5) Å | θ = 2.2–24.2° |
c = 13.3937 (16) Å | µ = 0.10 mm−1 |
β = 127.155 (7)° | T = 298 K |
V = 3321.3 (8) Å3 | Block, yellow |
Z = 8 | 0.31 × 0.24 × 0.18 mm |
Bruker APEX area-detector diffractometer | 5837 independent reflections |
Radiation source: fine-focus sealed tube | 4596 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
φ and ω scans | θmax = 25.0°, θmin = 1.1° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | h = −10→9 |
Tmin = 0.969, Tmax = 0.978 | k = −31→43 |
17376 measured reflections | l = −15→15 |
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)] = 0.084 | H-atom parameters constrained |
wR(F2) = 0.197 | w = 1/[σ2(Fo2) + (0.0805P)2 + 1.0761P] where P = (Fo2 + 2Fc2)/3 |
S = 1.23 | (Δ/σ)max = 0.001 |
5837 reflections | Δρmax = 0.27 e Å−3 |
476 parameters | Δρmin = −0.24 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0041 (8) |
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 | 0.2830 (4) | 0.77773 (7) | 0.1845 (2) | 0.0632 (7) | |
H1 | 0.2781 | 0.7970 | 0.2130 | 0.095* | |
O2 | 0.2315 (5) | 0.63006 (7) | 0.3851 (3) | 0.0803 (9) | |
O3 | 0.2078 (6) | 0.66537 (8) | 0.5008 (3) | 0.0940 (11) | |
O4 | 0.1932 (4) | 0.84480 (6) | 0.5249 (2) | 0.0523 (6) | |
O5 | 0.7367 (5) | 0.78438 (7) | 0.7005 (3) | 0.0700 (8) | |
H5 | 0.7304 | 0.8020 | 0.7353 | 0.105* | |
O6 | 0.7847 (6) | 0.80468 (11) | 0.2595 (4) | 0.1104 (13) | |
O7 | 0.7373 (5) | 0.86008 (11) | 0.2873 (3) | 0.0926 (10) | |
O8 | 0.6736 (4) | 0.93631 (6) | 0.7206 (2) | 0.0571 (7) | |
N1 | 0.2292 (5) | 0.66043 (8) | 0.4203 (3) | 0.0569 (8) | |
N2 | 0.2536 (4) | 0.82060 (7) | 0.3278 (2) | 0.0400 (6) | |
N3 | 0.2186 (4) | 0.91586 (7) | 0.3663 (2) | 0.0411 (7) | |
N4 | 0.2107 (4) | 0.90198 (7) | 0.4606 (2) | 0.0412 (7) | |
N5 | 0.7597 (5) | 0.82762 (13) | 0.3142 (3) | 0.0750 (10) | |
N6 | 0.7401 (4) | 0.85204 (7) | 0.7526 (3) | 0.0464 (7) | |
N7 | 0.7594 (4) | 0.90085 (8) | 0.9884 (3) | 0.0499 (7) | |
N8 | 0.7023 (4) | 0.92895 (7) | 0.9023 (3) | 0.0508 (7) | |
C1 | 0.2734 (5) | 0.75023 (9) | 0.2458 (3) | 0.0439 (8) | |
C2 | 0.2529 (5) | 0.75591 (8) | 0.3415 (3) | 0.0384 (7) | |
C3 | 0.2413 (5) | 0.72596 (8) | 0.3990 (3) | 0.0422 (8) | |
H3 | 0.2300 | 0.7291 | 0.4634 | 0.051* | |
C4 | 0.2464 (5) | 0.69151 (8) | 0.3615 (3) | 0.0448 (8) | |
C5 | 0.2663 (6) | 0.68606 (9) | 0.2676 (3) | 0.0530 (9) | |
H5A | 0.2688 | 0.6627 | 0.2426 | 0.064* | |
C6 | 0.2821 (6) | 0.71525 (10) | 0.2121 (3) | 0.0558 (10) | |
H6 | 0.2991 | 0.7116 | 0.1504 | 0.067* | |
C7 | 0.2448 (5) | 0.79222 (8) | 0.3793 (3) | 0.0409 (8) | |
H7 | 0.2327 | 0.7950 | 0.4434 | 0.049* | |
C8 | 0.2443 (4) | 0.85527 (8) | 0.3666 (3) | 0.0379 (7) | |
C9 | 0.2539 (5) | 0.88659 (8) | 0.3182 (3) | 0.0402 (8) | |
C10 | 0.2141 (5) | 0.86419 (8) | 0.4594 (3) | 0.0397 (8) | |
C11 | 0.1099 (5) | 0.92154 (8) | 0.4989 (3) | 0.0390 (7) | |
C12 | −0.0439 (5) | 0.94483 (10) | 0.4193 (3) | 0.0535 (9) | |
H12 | −0.0805 | 0.9493 | 0.3396 | 0.064* | |
C13 | −0.1440 (6) | 0.96161 (10) | 0.4590 (4) | 0.0606 (10) | |
H13 | −0.2477 | 0.9775 | 0.4057 | 0.073* | |
C14 | −0.0918 (6) | 0.95497 (10) | 0.5754 (4) | 0.0576 (10) | |
H14 | −0.1614 | 0.9659 | 0.6008 | 0.069* | |
C15 | 0.0633 (6) | 0.93211 (9) | 0.6551 (4) | 0.0551 (10) | |
H15 | 0.0991 | 0.9277 | 0.7347 | 0.066* | |
C16 | 0.1666 (5) | 0.91571 (9) | 0.6181 (3) | 0.0455 (8) | |
H16 | 0.2743 | 0.9007 | 0.6733 | 0.055* | |
C17 | 0.2970 (6) | 0.89201 (9) | 0.2266 (3) | 0.0547 (10) | |
H17A | 0.2918 | 0.8691 | 0.1908 | 0.082* | |
H17B | 0.4271 | 0.9024 | 0.2685 | 0.082* | |
H17C | 0.1998 | 0.9081 | 0.1614 | 0.082* | |
C18 | 0.3341 (6) | 0.94947 (9) | 0.4015 (4) | 0.0551 (9) | |
H18A | 0.4681 | 0.9452 | 0.4742 | 0.083* | |
H18B | 0.2750 | 0.9679 | 0.4200 | 0.083* | |
H18C | 0.3348 | 0.9573 | 0.3335 | 0.083* | |
C19 | 0.7455 (5) | 0.79567 (10) | 0.6090 (3) | 0.0513 (9) | |
C20 | 0.7461 (5) | 0.83279 (9) | 0.5852 (3) | 0.0431 (8) | |
C21 | 0.7523 (5) | 0.84263 (10) | 0.4880 (3) | 0.0493 (9) | |
H21 | 0.7527 | 0.8670 | 0.4703 | 0.059* | |
C22 | 0.7578 (5) | 0.81638 (11) | 0.4175 (3) | 0.0533 (9) | |
C23 | 0.7613 (6) | 0.77979 (11) | 0.4419 (4) | 0.0654 (11) | |
H23 | 0.7678 | 0.7624 | 0.3942 | 0.078* | |
C24 | 0.7549 (6) | 0.76974 (10) | 0.5375 (4) | 0.0634 (11) | |
H24 | 0.7569 | 0.7453 | 0.5549 | 0.076* | |
C25 | 0.7373 (5) | 0.86064 (9) | 0.6586 (3) | 0.0445 (8) | |
H25 | 0.7294 | 0.8849 | 0.6372 | 0.053* | |
C26 | 0.7324 (5) | 0.87798 (9) | 0.8248 (3) | 0.0445 (8) | |
C27 | 0.7632 (5) | 0.86986 (9) | 0.9344 (3) | 0.0467 (8) | |
C28 | 0.6992 (5) | 0.91661 (9) | 0.8030 (3) | 0.0435 (8) | |
C29 | 0.7209 (5) | 0.96573 (9) | 0.9400 (3) | 0.0454 (8) | |
C30 | 0.8807 (6) | 0.97718 (11) | 1.0564 (3) | 0.0587 (10) | |
H30 | 0.9780 | 0.9607 | 1.1130 | 0.070* | |
C31 | 0.8962 (7) | 1.01322 (12) | 1.0890 (4) | 0.0681 (11) | |
H31 | 1.0044 | 1.0210 | 1.1677 | 0.082* | |
C32 | 0.7532 (7) | 1.03746 (11) | 1.0061 (4) | 0.0689 (12) | |
H32 | 0.7634 | 1.0617 | 1.0282 | 0.083* | |
C33 | 0.5948 (7) | 1.02572 (11) | 0.8905 (4) | 0.0693 (11) | |
H33 | 0.4980 | 1.0422 | 0.8337 | 0.083* | |
C34 | 0.5771 (6) | 0.98988 (10) | 0.8572 (3) | 0.0577 (10) | |
H34 | 0.4680 | 0.9821 | 0.7788 | 0.069* | |
C35 | 0.7994 (6) | 0.83390 (11) | 0.9950 (4) | 0.0650 (11) | |
H35A | 0.9232 | 0.8345 | 1.0778 | 0.098* | |
H35B | 0.8051 | 0.8156 | 0.9463 | 0.098* | |
H35C | 0.6933 | 0.8284 | 1.0001 | 0.098* | |
C36 | 0.6904 (7) | 0.90264 (12) | 1.0652 (4) | 0.0740 (12) | |
H36A | 0.5477 | 0.9030 | 1.0120 | 0.111* | |
H36B | 0.7404 | 0.9243 | 1.1151 | 0.111* | |
H36C | 0.7376 | 0.8818 | 1.1191 | 0.111* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.100 (2) | 0.0493 (16) | 0.0590 (17) | 0.0050 (15) | 0.0582 (17) | 0.0032 (13) |
O2 | 0.114 (2) | 0.0326 (15) | 0.096 (2) | 0.0038 (15) | 0.064 (2) | 0.0013 (14) |
O3 | 0.167 (3) | 0.0579 (19) | 0.094 (2) | −0.0192 (19) | 0.098 (3) | −0.0056 (16) |
O4 | 0.0827 (18) | 0.0357 (13) | 0.0603 (16) | 0.0028 (11) | 0.0546 (15) | 0.0052 (11) |
O5 | 0.095 (2) | 0.0459 (16) | 0.087 (2) | −0.0007 (15) | 0.0643 (19) | 0.0048 (14) |
O6 | 0.132 (3) | 0.137 (3) | 0.108 (3) | −0.021 (2) | 0.096 (3) | −0.045 (2) |
O7 | 0.109 (3) | 0.114 (3) | 0.074 (2) | 0.014 (2) | 0.065 (2) | 0.014 (2) |
O8 | 0.0828 (19) | 0.0489 (15) | 0.0377 (14) | 0.0002 (12) | 0.0354 (14) | 0.0024 (11) |
N1 | 0.069 (2) | 0.0367 (18) | 0.056 (2) | −0.0057 (14) | 0.0329 (18) | −0.0011 (14) |
N2 | 0.0449 (16) | 0.0360 (16) | 0.0426 (16) | 0.0018 (12) | 0.0282 (14) | 0.0001 (12) |
N3 | 0.0512 (17) | 0.0320 (15) | 0.0457 (16) | 0.0001 (12) | 0.0323 (15) | 0.0032 (12) |
N4 | 0.0536 (17) | 0.0350 (15) | 0.0439 (16) | 0.0029 (12) | 0.0341 (15) | 0.0027 (12) |
N5 | 0.065 (2) | 0.106 (3) | 0.065 (2) | −0.007 (2) | 0.045 (2) | −0.017 (2) |
N6 | 0.0459 (17) | 0.0459 (17) | 0.0412 (16) | −0.0001 (12) | 0.0231 (15) | −0.0009 (13) |
N7 | 0.0594 (19) | 0.0552 (19) | 0.0366 (16) | 0.0026 (14) | 0.0297 (16) | 0.0057 (13) |
N8 | 0.0623 (19) | 0.0464 (18) | 0.0376 (16) | 0.0034 (14) | 0.0270 (15) | 0.0008 (13) |
C1 | 0.049 (2) | 0.042 (2) | 0.0382 (19) | 0.0038 (15) | 0.0249 (17) | 0.0025 (15) |
C2 | 0.0392 (18) | 0.0368 (18) | 0.0355 (17) | −0.0010 (13) | 0.0206 (15) | −0.0039 (14) |
C3 | 0.047 (2) | 0.044 (2) | 0.0371 (18) | −0.0021 (15) | 0.0261 (17) | −0.0029 (15) |
C4 | 0.049 (2) | 0.0354 (19) | 0.043 (2) | 0.0001 (15) | 0.0241 (17) | −0.0029 (14) |
C5 | 0.065 (2) | 0.038 (2) | 0.048 (2) | 0.0043 (16) | 0.029 (2) | −0.0065 (16) |
C6 | 0.080 (3) | 0.051 (2) | 0.045 (2) | 0.0077 (18) | 0.042 (2) | −0.0048 (17) |
C7 | 0.048 (2) | 0.0401 (19) | 0.0394 (19) | 0.0010 (15) | 0.0292 (17) | −0.0018 (15) |
C8 | 0.0382 (18) | 0.0358 (18) | 0.0412 (18) | 0.0036 (13) | 0.0248 (16) | 0.0014 (14) |
C9 | 0.0382 (18) | 0.0402 (19) | 0.0424 (19) | 0.0035 (14) | 0.0244 (16) | 0.0038 (14) |
C10 | 0.0403 (18) | 0.0350 (18) | 0.0424 (19) | 0.0004 (14) | 0.0242 (17) | 0.0031 (14) |
C11 | 0.048 (2) | 0.0272 (17) | 0.0436 (19) | −0.0048 (14) | 0.0285 (17) | −0.0035 (14) |
C12 | 0.059 (2) | 0.059 (2) | 0.037 (2) | 0.0081 (18) | 0.0264 (19) | −0.0005 (16) |
C13 | 0.061 (2) | 0.061 (3) | 0.055 (2) | 0.0158 (19) | 0.032 (2) | 0.0028 (18) |
C14 | 0.069 (3) | 0.056 (2) | 0.062 (3) | 0.0045 (19) | 0.047 (2) | −0.0080 (19) |
C15 | 0.078 (3) | 0.048 (2) | 0.051 (2) | −0.0010 (19) | 0.045 (2) | −0.0037 (17) |
C16 | 0.054 (2) | 0.0368 (19) | 0.043 (2) | 0.0025 (15) | 0.0279 (18) | 0.0009 (14) |
C17 | 0.074 (3) | 0.047 (2) | 0.062 (2) | 0.0091 (18) | 0.051 (2) | 0.0103 (17) |
C18 | 0.070 (3) | 0.041 (2) | 0.062 (2) | −0.0082 (17) | 0.044 (2) | 0.0000 (16) |
C19 | 0.042 (2) | 0.048 (2) | 0.055 (2) | −0.0043 (16) | 0.0253 (19) | −0.0055 (17) |
C20 | 0.0364 (18) | 0.0397 (19) | 0.046 (2) | −0.0012 (14) | 0.0209 (17) | −0.0047 (15) |
C21 | 0.044 (2) | 0.052 (2) | 0.045 (2) | −0.0031 (16) | 0.0228 (18) | −0.0039 (16) |
C22 | 0.045 (2) | 0.066 (3) | 0.049 (2) | −0.0065 (17) | 0.0285 (19) | −0.0123 (18) |
C23 | 0.054 (2) | 0.065 (3) | 0.078 (3) | −0.0115 (19) | 0.040 (2) | −0.030 (2) |
C24 | 0.056 (2) | 0.043 (2) | 0.086 (3) | −0.0038 (17) | 0.040 (2) | −0.013 (2) |
C25 | 0.0416 (19) | 0.0397 (19) | 0.044 (2) | −0.0028 (14) | 0.0217 (17) | −0.0023 (15) |
C26 | 0.0399 (19) | 0.046 (2) | 0.040 (2) | −0.0016 (15) | 0.0203 (17) | −0.0001 (15) |
C27 | 0.043 (2) | 0.047 (2) | 0.043 (2) | −0.0026 (15) | 0.0222 (17) | 0.0008 (16) |
C28 | 0.0424 (19) | 0.049 (2) | 0.0306 (18) | −0.0003 (15) | 0.0175 (16) | −0.0035 (15) |
C29 | 0.049 (2) | 0.053 (2) | 0.0354 (19) | 0.0022 (16) | 0.0259 (18) | −0.0048 (15) |
C30 | 0.058 (2) | 0.066 (3) | 0.044 (2) | 0.0105 (19) | 0.026 (2) | −0.0037 (18) |
C31 | 0.071 (3) | 0.074 (3) | 0.050 (2) | −0.006 (2) | 0.033 (2) | −0.022 (2) |
C32 | 0.100 (4) | 0.054 (3) | 0.069 (3) | −0.002 (2) | 0.060 (3) | −0.014 (2) |
C33 | 0.084 (3) | 0.056 (3) | 0.062 (3) | 0.013 (2) | 0.041 (3) | 0.003 (2) |
C34 | 0.057 (2) | 0.054 (2) | 0.043 (2) | 0.0029 (18) | 0.0208 (19) | −0.0009 (17) |
C35 | 0.078 (3) | 0.061 (3) | 0.055 (2) | 0.003 (2) | 0.040 (2) | 0.0120 (19) |
C36 | 0.089 (3) | 0.084 (3) | 0.069 (3) | −0.002 (2) | 0.058 (3) | −0.001 (2) |
O1—C1 | 1.338 (4) | C13—C14 | 1.363 (5) |
O1—H1 | 0.8200 | C13—H13 | 0.9300 |
O2—N1 | 1.220 (4) | C14—C15 | 1.369 (5) |
O3—N1 | 1.210 (4) | C14—H14 | 0.9300 |
O4—C10 | 1.224 (4) | C15—C16 | 1.376 (5) |
O5—C19 | 1.337 (4) | C15—H15 | 0.9300 |
O5—H5 | 0.8200 | C16—H16 | 0.9300 |
O6—N5 | 1.218 (5) | C17—H17A | 0.9600 |
O7—N5 | 1.231 (5) | C17—H17B | 0.9600 |
O8—C28 | 1.227 (4) | C17—H17C | 0.9600 |
N1—C4 | 1.447 (4) | C18—H18A | 0.9600 |
N2—C7 | 1.280 (4) | C18—H18B | 0.9600 |
N2—C8 | 1.400 (4) | C18—H18C | 0.9600 |
N3—C9 | 1.379 (4) | C19—C24 | 1.389 (5) |
N3—N4 | 1.402 (3) | C19—C20 | 1.406 (5) |
N3—C18 | 1.467 (4) | C20—C21 | 1.383 (5) |
N4—C10 | 1.394 (4) | C20—C25 | 1.454 (5) |
N4—C11 | 1.426 (4) | C21—C22 | 1.372 (5) |
N5—C22 | 1.453 (5) | C21—H21 | 0.9300 |
N6—C25 | 1.285 (4) | C22—C23 | 1.384 (5) |
N6—C26 | 1.389 (4) | C23—C24 | 1.364 (6) |
N7—C27 | 1.363 (4) | C23—H23 | 0.9300 |
N7—N8 | 1.402 (4) | C24—H24 | 0.9300 |
N7—C36 | 1.458 (5) | C25—H25 | 0.9300 |
N8—C28 | 1.391 (4) | C26—C27 | 1.361 (5) |
N8—C29 | 1.422 (4) | C26—C28 | 1.447 (5) |
C1—C6 | 1.383 (5) | C27—C35 | 1.487 (5) |
C1—C2 | 1.408 (4) | C29—C34 | 1.368 (5) |
C2—C3 | 1.383 (4) | C29—C30 | 1.374 (5) |
C2—C7 | 1.447 (4) | C30—C31 | 1.380 (5) |
C3—C4 | 1.376 (4) | C30—H30 | 0.9300 |
C3—H3 | 0.9300 | C31—C32 | 1.367 (6) |
C4—C5 | 1.380 (5) | C31—H31 | 0.9300 |
C5—C6 | 1.360 (5) | C32—C33 | 1.368 (6) |
C5—H5A | 0.9300 | C32—H32 | 0.9300 |
C6—H6 | 0.9300 | C33—C34 | 1.374 (5) |
C7—H7 | 0.9300 | C33—H33 | 0.9300 |
C8—C9 | 1.351 (4) | C34—H34 | 0.9300 |
C8—C10 | 1.449 (4) | C35—H35A | 0.9600 |
C9—C17 | 1.488 (4) | C35—H35B | 0.9600 |
C11—C12 | 1.374 (5) | C35—H35C | 0.9600 |
C11—C16 | 1.378 (4) | C36—H36A | 0.9600 |
C12—C13 | 1.385 (5) | C36—H36B | 0.9600 |
C12—H12 | 0.9300 | C36—H36C | 0.9600 |
C1—O1—H1 | 109.5 | C9—C17—H17B | 109.5 |
C19—O5—H5 | 109.5 | H17A—C17—H17B | 109.5 |
O3—N1—O2 | 121.9 (3) | C9—C17—H17C | 109.5 |
O3—N1—C4 | 119.0 (3) | H17A—C17—H17C | 109.5 |
O2—N1—C4 | 119.1 (3) | H17B—C17—H17C | 109.5 |
C7—N2—C8 | 120.8 (3) | N3—C18—H18A | 109.5 |
C9—N3—N4 | 106.1 (2) | N3—C18—H18B | 109.5 |
C9—N3—C18 | 121.5 (3) | H18A—C18—H18B | 109.5 |
N4—N3—C18 | 113.7 (3) | N3—C18—H18C | 109.5 |
C10—N4—N3 | 110.0 (2) | H18A—C18—H18C | 109.5 |
C10—N4—C11 | 122.1 (2) | H18B—C18—H18C | 109.5 |
N3—N4—C11 | 120.2 (2) | O5—C19—C24 | 118.4 (3) |
O6—N5—O7 | 123.4 (4) | O5—C19—C20 | 121.4 (3) |
O6—N5—C22 | 118.7 (5) | C24—C19—C20 | 120.2 (4) |
O7—N5—C22 | 118.0 (4) | C21—C20—C19 | 118.5 (3) |
C25—N6—C26 | 122.1 (3) | C21—C20—C25 | 119.8 (3) |
C27—N7—N8 | 106.8 (3) | C19—C20—C25 | 121.7 (3) |
C27—N7—C36 | 124.1 (3) | C22—C21—C20 | 119.9 (3) |
N8—N7—C36 | 117.5 (3) | C22—C21—H21 | 120.0 |
C28—N8—N7 | 110.1 (3) | C20—C21—H21 | 120.0 |
C28—N8—C29 | 125.9 (3) | C21—C22—C23 | 122.0 (4) |
N7—N8—C29 | 120.2 (3) | C21—C22—N5 | 118.5 (4) |
O1—C1—C6 | 118.1 (3) | C23—C22—N5 | 119.5 (4) |
O1—C1—C2 | 122.1 (3) | C24—C23—C22 | 118.6 (3) |
C6—C1—C2 | 119.7 (3) | C24—C23—H23 | 120.7 |
C3—C2—C1 | 118.5 (3) | C22—C23—H23 | 120.7 |
C3—C2—C7 | 120.6 (3) | C23—C24—C19 | 120.7 (4) |
C1—C2—C7 | 120.9 (3) | C23—C24—H24 | 119.6 |
C4—C3—C2 | 120.3 (3) | C19—C24—H24 | 119.6 |
C4—C3—H3 | 119.8 | N6—C25—C20 | 120.7 (3) |
C2—C3—H3 | 119.8 | N6—C25—H25 | 119.7 |
C3—C4—C5 | 121.0 (3) | C20—C25—H25 | 119.7 |
C3—C4—N1 | 119.8 (3) | C27—C26—N6 | 122.7 (3) |
C5—C4—N1 | 119.2 (3) | C27—C26—C28 | 108.8 (3) |
C6—C5—C4 | 119.3 (3) | N6—C26—C28 | 128.5 (3) |
C6—C5—H5A | 120.4 | C26—C27—N7 | 109.8 (3) |
C4—C5—H5A | 120.4 | C26—C27—C35 | 128.9 (3) |
C5—C6—C1 | 121.1 (3) | N7—C27—C35 | 121.4 (3) |
C5—C6—H6 | 119.4 | O8—C28—N8 | 123.9 (3) |
C1—C6—H6 | 119.4 | O8—C28—C26 | 132.2 (3) |
N2—C7—C2 | 122.5 (3) | N8—C28—C26 | 103.9 (3) |
N2—C7—H7 | 118.7 | C34—C29—C30 | 120.1 (3) |
C2—C7—H7 | 118.7 | C34—C29—N8 | 118.6 (3) |
C9—C8—N2 | 124.7 (3) | C30—C29—N8 | 121.2 (3) |
C9—C8—C10 | 108.1 (3) | C29—C30—C31 | 119.7 (4) |
N2—C8—C10 | 127.2 (3) | C29—C30—H30 | 120.1 |
C8—C9—N3 | 110.6 (3) | C31—C30—H30 | 120.1 |
C8—C9—C17 | 128.8 (3) | C32—C31—C30 | 120.3 (4) |
N3—C9—C17 | 120.6 (3) | C32—C31—H31 | 119.9 |
O4—C10—N4 | 124.2 (3) | C30—C31—H31 | 119.9 |
O4—C10—C8 | 131.1 (3) | C31—C32—C33 | 119.5 (4) |
N4—C10—C8 | 104.6 (3) | C31—C32—H32 | 120.3 |
C12—C11—C16 | 120.0 (3) | C33—C32—H32 | 120.3 |
C12—C11—N4 | 121.8 (3) | C32—C33—C34 | 120.8 (4) |
C16—C11—N4 | 118.2 (3) | C32—C33—H33 | 119.6 |
C11—C12—C13 | 119.4 (3) | C34—C33—H33 | 119.6 |
C11—C12—H12 | 120.3 | C29—C34—C33 | 119.6 (4) |
C13—C12—H12 | 120.3 | C29—C34—H34 | 120.2 |
C14—C13—C12 | 120.5 (4) | C33—C34—H34 | 120.2 |
C14—C13—H13 | 119.7 | C27—C35—H35A | 109.5 |
C12—C13—H13 | 119.7 | C27—C35—H35B | 109.5 |
C13—C14—C15 | 119.9 (3) | H35A—C35—H35B | 109.5 |
C13—C14—H14 | 120.0 | C27—C35—H35C | 109.5 |
C15—C14—H14 | 120.0 | H35A—C35—H35C | 109.5 |
C14—C15—C16 | 120.3 (3) | H35B—C35—H35C | 109.5 |
C14—C15—H15 | 119.8 | N7—C36—H36A | 109.5 |
C16—C15—H15 | 119.8 | N7—C36—H36B | 109.5 |
C15—C16—C11 | 119.8 (3) | H36A—C36—H36B | 109.5 |
C15—C16—H16 | 120.1 | N7—C36—H36C | 109.5 |
C11—C16—H16 | 120.1 | H36A—C36—H36C | 109.5 |
C9—C17—H17A | 109.5 | H36B—C36—H36C | 109.5 |
C9—N3—N4—C10 | −7.9 (3) | C13—C14—C15—C16 | −0.2 (6) |
C18—N3—N4—C10 | −144.0 (3) | C14—C15—C16—C11 | −1.8 (5) |
C9—N3—N4—C11 | −157.8 (3) | C12—C11—C16—C15 | 2.7 (5) |
C18—N3—N4—C11 | 66.1 (4) | N4—C11—C16—C15 | −175.4 (3) |
C27—N7—N8—C28 | −8.8 (4) | O5—C19—C20—C21 | −179.0 (3) |
C36—N7—N8—C28 | −153.6 (3) | C24—C19—C20—C21 | 1.3 (5) |
C27—N7—N8—C29 | −168.0 (3) | O5—C19—C20—C25 | 0.0 (5) |
C36—N7—N8—C29 | 47.2 (4) | C24—C19—C20—C25 | −179.7 (3) |
O1—C1—C2—C3 | 179.1 (3) | C19—C20—C21—C22 | −0.1 (5) |
C6—C1—C2—C3 | −0.2 (5) | C25—C20—C21—C22 | −179.1 (3) |
O1—C1—C2—C7 | −1.1 (5) | C20—C21—C22—C23 | −1.3 (5) |
C6—C1—C2—C7 | 179.6 (3) | C20—C21—C22—N5 | 178.6 (3) |
C1—C2—C3—C4 | −1.1 (5) | O6—N5—C22—C21 | 172.7 (4) |
C7—C2—C3—C4 | 179.1 (3) | O7—N5—C22—C21 | −6.7 (5) |
C2—C3—C4—C5 | 1.1 (5) | O6—N5—C22—C23 | −7.4 (5) |
C2—C3—C4—N1 | −178.5 (3) | O7—N5—C22—C23 | 173.2 (4) |
O3—N1—C4—C3 | 1.0 (5) | C21—C22—C23—C24 | 1.4 (6) |
O2—N1—C4—C3 | 179.1 (3) | N5—C22—C23—C24 | −178.5 (3) |
O3—N1—C4—C5 | −178.5 (4) | C22—C23—C24—C19 | −0.1 (6) |
O2—N1—C4—C5 | −0.4 (5) | O5—C19—C24—C23 | 179.1 (4) |
C3—C4—C5—C6 | 0.4 (5) | C20—C19—C24—C23 | −1.2 (6) |
N1—C4—C5—C6 | 179.9 (3) | C26—N6—C25—C20 | 179.8 (3) |
C4—C5—C6—C1 | −1.7 (6) | C21—C20—C25—N6 | −177.0 (3) |
O1—C1—C6—C5 | −177.7 (3) | C19—C20—C25—N6 | 4.1 (5) |
C2—C1—C6—C5 | 1.7 (5) | C25—N6—C26—C27 | −170.6 (3) |
C8—N2—C7—C2 | 179.7 (3) | C25—N6—C26—C28 | 7.3 (5) |
C3—C2—C7—N2 | −179.5 (3) | N6—C26—C27—N7 | 176.1 (3) |
C1—C2—C7—N2 | 0.7 (5) | C28—C26—C27—N7 | −2.2 (4) |
C7—N2—C8—C9 | 179.5 (3) | N6—C26—C27—C35 | −3.1 (6) |
C7—N2—C8—C10 | −3.5 (5) | C28—C26—C27—C35 | 178.6 (4) |
N2—C8—C9—N3 | 173.4 (3) | N8—N7—C27—C26 | 6.6 (4) |
C10—C8—C9—N3 | −4.1 (4) | C36—N7—C27—C26 | 148.5 (3) |
N2—C8—C9—C17 | −7.1 (6) | N8—N7—C27—C35 | −174.1 (3) |
C10—C8—C9—C17 | 175.4 (3) | C36—N7—C27—C35 | −32.2 (5) |
N4—N3—C9—C8 | 7.4 (4) | N7—N8—C28—O8 | −172.5 (3) |
C18—N3—C9—C8 | 139.3 (3) | C29—N8—C28—O8 | −14.8 (5) |
N4—N3—C9—C17 | −172.2 (3) | N7—N8—C28—C26 | 7.3 (3) |
C18—N3—C9—C17 | −40.3 (4) | C29—N8—C28—C26 | 165.0 (3) |
N3—N4—C10—O4 | −174.0 (3) | C27—C26—C28—O8 | 176.6 (4) |
C11—N4—C10—O4 | −24.8 (5) | N6—C26—C28—O8 | −1.5 (6) |
N3—N4—C10—C8 | 5.4 (3) | C27—C26—C28—N8 | −3.2 (4) |
C11—N4—C10—C8 | 154.7 (3) | N6—C26—C28—N8 | 178.7 (3) |
C9—C8—C10—O4 | 178.6 (3) | C28—N8—C29—C34 | 61.6 (5) |
N2—C8—C10—O4 | 1.2 (6) | N7—N8—C29—C34 | −142.7 (3) |
C9—C8—C10—N4 | −0.8 (3) | C28—N8—C29—C30 | −117.5 (4) |
N2—C8—C10—N4 | −178.2 (3) | N7—N8—C29—C30 | 38.1 (5) |
C10—N4—C11—C12 | −119.3 (4) | C34—C29—C30—C31 | −0.5 (6) |
N3—N4—C11—C12 | 26.9 (4) | N8—C29—C30—C31 | 178.7 (3) |
C10—N4—C11—C16 | 58.7 (4) | C29—C30—C31—C32 | 0.1 (6) |
N3—N4—C11—C16 | −155.1 (3) | C30—C31—C32—C33 | −0.2 (6) |
C16—C11—C12—C13 | −1.6 (5) | C31—C32—C33—C34 | 0.6 (6) |
N4—C11—C12—C13 | 176.4 (3) | C30—C29—C34—C33 | 0.9 (6) |
C11—C12—C13—C14 | −0.4 (6) | N8—C29—C34—C33 | −178.3 (3) |
C12—C13—C14—C15 | 1.3 (6) | C32—C33—C34—C29 | −0.9 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···N2 | 0.82 | 1.88 | 2.612 (3) | 147 |
O5—H5···N6 | 0.82 | 1.86 | 2.586 (4) | 148 |