Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806024147/er2008sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806024147/er2008Isup2.hkl |
CCDC reference: 613672
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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: SHELXTL.
C21H17N3O2·0.5C3H6O | Z = 4 |
Mr = 372.42 | F(000) = 784 |
Triclinic, P1 | Dx = 1.310 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 11.605 (2) Å | Cell parameters from 3213 reflections |
b = 12.150 (2) Å | θ = 2.1–24.9° |
c = 14.846 (3) Å | µ = 0.09 mm−1 |
α = 75.68 (3)° | T = 298 K |
β = 68.86 (3)° | Block, brown |
γ = 81.52 (3)° | 0.38 × 0.26 × 0.13 mm |
V = 1887.8 (7) Å3 |
Bruker SMART CCD area-detector diffractometer | 7750 independent reflections |
Radiation source: fine-focus sealed tube | 4059 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
Detector resolution: 10 pixels mm-1 | θmax = 26.5°, θmin = 2.3° |
ω scans | h = −14→14 |
Absorption correction: multi-scan (SADABS; Sheldrick, 2002) | k = −15→15 |
Tmin = 0.968, Tmax = 0.989 | l = −18→18 |
15422 measured 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)] = 0.053 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.180 | H-atom parameters constrained |
S = 0.92 | w = 1/[σ2(Fo2) + (0.088P)2] where P = (Fo2 + 2Fc2)/3 |
7750 reflections | (Δ/σ)max < 0.001 |
502 parameters | Δρmax = 0.18 e Å−3 |
15 restraints | Δρmin = −0.43 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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.97988 (16) | 1.10344 (15) | 0.87876 (14) | 0.0937 (5) | |
O2 | 1.0017 (2) | 1.09669 (17) | 0.73040 (15) | 0.1140 (7) | |
O3 | 0.6864 (2) | 0.50524 (18) | 0.48253 (16) | 0.1182 (7) | |
O4 | 0.8617 (3) | 0.54486 (19) | 0.36606 (19) | 0.1339 (8) | |
N1 | 0.97942 (17) | 1.05098 (18) | 0.81774 (16) | 0.0775 (5) | |
N2 | 0.87047 (17) | 0.59428 (17) | 0.94109 (13) | 0.0720 (5) | |
N3 | 0.83438 (16) | 0.54225 (16) | 1.04029 (13) | 0.0694 (5) | |
N4 | 0.7504 (3) | 0.5665 (2) | 0.4054 (2) | 0.0956 (7) | |
N5 | 0.51804 (15) | 0.94397 (15) | 0.22371 (13) | 0.0694 (5) | |
N6 | 0.58305 (16) | 1.00775 (15) | 0.13258 (13) | 0.0650 (5) | |
C1 | 0.94959 (18) | 0.9332 (2) | 0.84984 (16) | 0.0656 (6) | |
C2 | 0.96232 (19) | 0.8703 (2) | 0.78037 (16) | 0.0715 (6) | |
H2 | 0.9891 | 0.9040 | 0.7135 | 0.086* | |
C3 | 0.93554 (19) | 0.7589 (2) | 0.81043 (16) | 0.0712 (6) | |
H3 | 0.9436 | 0.7169 | 0.7637 | 0.085* | |
C4 | 0.89592 (18) | 0.70679 (19) | 0.91120 (15) | 0.0629 (5) | |
C5 | 0.88316 (19) | 0.77275 (19) | 0.98010 (15) | 0.0645 (5) | |
H5 | 0.8556 | 0.7401 | 1.0472 | 0.077* | |
C6 | 0.91074 (19) | 0.8842 (2) | 0.94949 (16) | 0.0665 (6) | |
H6 | 0.9034 | 0.9270 | 0.9955 | 0.080* | |
C7 | 0.8730 (2) | 0.51729 (19) | 0.87667 (16) | 0.0709 (6) | |
H7 | 0.9552 | 0.5138 | 0.8263 | 0.085* | |
C8 | 0.8510 (3) | 0.4034 (2) | 0.95132 (18) | 0.0838 (7) | |
H8A | 0.7826 | 0.3675 | 0.9498 | 0.101* | |
H8B | 0.9246 | 0.3519 | 0.9380 | 0.101* | |
C9 | 0.82100 (19) | 0.4360 (2) | 1.04872 (17) | 0.0673 (6) | |
C10 | 0.78149 (19) | 0.35819 (19) | 1.14498 (18) | 0.0684 (6) | |
C11 | 0.7568 (2) | 0.3944 (2) | 1.23223 (19) | 0.0805 (7) | |
H11 | 0.7649 | 0.4702 | 1.2297 | 0.097* | |
C12 | 0.7204 (3) | 0.3199 (2) | 1.3224 (2) | 0.0920 (8) | |
H12 | 0.7038 | 0.3459 | 1.3800 | 0.110* | |
C13 | 0.7085 (2) | 0.2067 (2) | 1.3281 (2) | 0.0915 (8) | |
H13 | 0.6849 | 0.1563 | 1.3890 | 0.110* | |
C14 | 0.7318 (2) | 0.1696 (2) | 1.2433 (2) | 0.0872 (7) | |
H14 | 0.7235 | 0.0936 | 1.2468 | 0.105* | |
C15 | 0.7674 (2) | 0.2436 (2) | 1.1522 (2) | 0.0782 (7) | |
H15 | 0.7821 | 0.2170 | 1.0952 | 0.094* | |
C16 | 0.7761 (2) | 0.55473 (18) | 0.82794 (16) | 0.0664 (5) | |
C17 | 0.8055 (3) | 0.5635 (2) | 0.7286 (2) | 0.0973 (8) | |
H17 | 0.8864 | 0.5468 | 0.6898 | 0.117* | |
C18 | 0.7125 (4) | 0.5979 (3) | 0.6860 (3) | 0.1269 (12) | |
H18 | 0.7319 | 0.6041 | 0.6185 | 0.152* | |
C19 | 0.5943 (4) | 0.6222 (3) | 0.7424 (4) | 0.1286 (13) | |
H19 | 0.5334 | 0.6457 | 0.7135 | 0.154* | |
C20 | 0.5658 (3) | 0.6124 (2) | 0.8397 (3) | 0.1106 (10) | |
H20 | 0.4846 | 0.6283 | 0.8782 | 0.133* | |
C21 | 0.6548 (2) | 0.5790 (2) | 0.8833 (2) | 0.0820 (7) | |
H21 | 0.6333 | 0.5727 | 0.9510 | 0.098* | |
C22 | 0.6906 (2) | 0.66509 (19) | 0.35886 (17) | 0.0726 (6) | |
C23 | 0.7607 (2) | 0.7386 (2) | 0.27754 (17) | 0.0723 (6) | |
H23 | 0.8463 | 0.7252 | 0.2532 | 0.087* | |
C24 | 0.7045 (2) | 0.83167 (19) | 0.23235 (16) | 0.0675 (6) | |
H24 | 0.7522 | 0.8811 | 0.1772 | 0.081* | |
C25 | 0.5752 (2) | 0.85295 (18) | 0.26883 (16) | 0.0641 (5) | |
C26 | 0.5061 (2) | 0.7773 (2) | 0.35322 (17) | 0.0750 (6) | |
H26 | 0.4207 | 0.7907 | 0.3792 | 0.090* | |
C27 | 0.5632 (2) | 0.6843 (2) | 0.39752 (17) | 0.0772 (6) | |
H27 | 0.5169 | 0.6344 | 0.4530 | 0.093* | |
C28 | 0.50552 (19) | 1.07628 (19) | 0.09797 (16) | 0.0644 (5) | |
C29 | 0.5450 (2) | 1.15394 (18) | 0.00191 (16) | 0.0640 (5) | |
C30 | 0.6693 (2) | 1.16301 (19) | −0.05582 (17) | 0.0704 (6) | |
H30 | 0.7297 | 1.1192 | −0.0327 | 0.085* | |
C31 | 0.7040 (2) | 1.2364 (2) | −0.14712 (18) | 0.0803 (7) | |
H31 | 0.7874 | 1.2411 | −0.1851 | 0.096* | |
C32 | 0.6161 (3) | 1.3028 (2) | −0.1823 (2) | 0.0876 (7) | |
H32 | 0.6397 | 1.3527 | −0.2435 | 0.105* | |
C33 | 0.4928 (3) | 1.2943 (2) | −0.1257 (2) | 0.0926 (8) | |
H33 | 0.4328 | 1.3386 | −0.1491 | 0.111* | |
C34 | 0.4575 (2) | 1.2211 (2) | −0.03518 (19) | 0.0801 (7) | |
H34 | 0.3738 | 1.2164 | 0.0020 | 0.096* | |
C35 | 0.37363 (19) | 1.0660 (2) | 0.16543 (17) | 0.0765 (6) | |
H35A | 0.3240 | 1.0415 | 0.1345 | 0.092* | |
H35B | 0.3375 | 1.1378 | 0.1839 | 0.092* | |
C36 | 0.38346 (18) | 0.97587 (19) | 0.25505 (17) | 0.0703 (6) | |
H36 | 0.3383 | 0.9101 | 0.2628 | 0.084* | |
C37 | 0.33697 (19) | 1.01791 (18) | 0.35070 (16) | 0.0658 (6) | |
C38 | 0.2159 (2) | 1.0073 (3) | 0.41003 (19) | 0.0947 (8) | |
H38 | 0.1635 | 0.9715 | 0.3930 | 0.114* | |
C39 | 0.1713 (3) | 1.0501 (3) | 0.4958 (2) | 0.1139 (10) | |
H39 | 0.0886 | 1.0431 | 0.5352 | 0.137* | |
C40 | 0.2443 (3) | 1.1010 (2) | 0.5230 (2) | 0.0957 (8) | |
H40 | 0.2130 | 1.1297 | 0.5803 | 0.115* | |
C41 | 0.3634 (3) | 1.1097 (3) | 0.4660 (2) | 0.1112 (10) | |
H41 | 0.4153 | 1.1441 | 0.4846 | 0.133* | |
C42 | 0.4105 (2) | 1.0685 (2) | 0.3802 (2) | 0.1018 (9) | |
H42 | 0.4936 | 1.0753 | 0.3419 | 0.122* | |
O5 | 0.1969 (5) | 0.7063 (5) | 0.4272 (5) | 0.176 (3)* | 0.584 (10) |
C43 | 0.0664 (7) | 0.7434 (6) | 0.5528 (5) | 0.125 (3)* | 0.584 (10) |
H43A | 0.1067 | 0.8137 | 0.5293 | 0.188* | 0.584 (10) |
H43B | 0.1048 | 0.6907 | 0.5951 | 0.188* | 0.584 (10) |
H43C | −0.0195 | 0.7575 | 0.5891 | 0.188* | 0.584 (10) |
C44 | 0.0766 (7) | 0.6985 (5) | 0.4740 (5) | 0.231 (3)* | 0.584 (10) |
C45 | 0.0547 (11) | 0.6562 (10) | 0.4098 (8) | 0.199 (5)* | 0.584 (10) |
H45A | 0.1233 | 0.6054 | 0.3829 | 0.299* | 0.584 (10) |
H45B | 0.0437 | 0.7168 | 0.3575 | 0.299* | 0.584 (10) |
H45C | −0.0191 | 0.6152 | 0.4416 | 0.299* | 0.584 (10) |
O5' | 0.152 (2) | 0.7212 (17) | 0.3819 (10) | 0.402 (11)* | 0.416 (10) |
C43' | 0.1377 (17) | 0.7732 (12) | 0.4954 (14) | 0.225 (7)* | 0.416 (10) |
H43D | 0.2017 | 0.7317 | 0.5192 | 0.338* | 0.416 (10) |
H43E | 0.0799 | 0.8107 | 0.5451 | 0.338* | 0.416 (10) |
H43F | 0.1737 | 0.8289 | 0.4367 | 0.338* | 0.416 (10) |
C44' | 0.0766 (7) | 0.6985 (5) | 0.4740 (5) | 0.231 (3)* | 0.416 (10) |
C45' | 0.0008 (13) | 0.6457 (10) | 0.4484 (10) | 0.153 (4)* | 0.416 (10) |
H45D | 0.0272 | 0.5664 | 0.4527 | 0.229* | 0.416 (10) |
H45E | 0.0044 | 0.6801 | 0.3819 | 0.229* | 0.416 (10) |
H45F | −0.0827 | 0.6533 | 0.4925 | 0.229* | 0.416 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0910 (12) | 0.0962 (13) | 0.0966 (13) | −0.0251 (10) | −0.0306 (10) | −0.0157 (11) |
O2 | 0.1315 (17) | 0.1073 (14) | 0.0748 (13) | −0.0212 (12) | −0.0104 (11) | 0.0018 (11) |
O3 | 0.153 (2) | 0.1027 (14) | 0.0982 (15) | −0.0163 (14) | −0.0542 (14) | 0.0034 (12) |
O4 | 0.1092 (18) | 0.1206 (17) | 0.162 (2) | 0.0127 (14) | −0.0616 (16) | 0.0008 (15) |
N1 | 0.0592 (11) | 0.0914 (15) | 0.0712 (14) | −0.0109 (10) | −0.0124 (10) | −0.0094 (12) |
N2 | 0.0813 (13) | 0.0822 (13) | 0.0633 (12) | −0.0048 (10) | −0.0320 (10) | −0.0235 (10) |
N3 | 0.0690 (11) | 0.0802 (13) | 0.0655 (12) | −0.0084 (9) | −0.0265 (9) | −0.0192 (10) |
N4 | 0.115 (2) | 0.0845 (16) | 0.0976 (18) | −0.0066 (15) | −0.0518 (17) | −0.0136 (14) |
N5 | 0.0518 (10) | 0.0738 (12) | 0.0713 (12) | −0.0004 (9) | −0.0050 (9) | −0.0212 (10) |
N6 | 0.0544 (10) | 0.0670 (11) | 0.0688 (11) | −0.0016 (9) | −0.0088 (9) | −0.0251 (9) |
C1 | 0.0453 (11) | 0.0834 (15) | 0.0626 (14) | −0.0079 (10) | −0.0140 (10) | −0.0096 (12) |
C2 | 0.0522 (12) | 0.1004 (18) | 0.0579 (13) | −0.0053 (12) | −0.0158 (10) | −0.0138 (13) |
C3 | 0.0576 (13) | 0.0997 (18) | 0.0625 (14) | −0.0032 (12) | −0.0219 (10) | −0.0272 (13) |
C4 | 0.0497 (11) | 0.0828 (15) | 0.0607 (13) | −0.0012 (10) | −0.0219 (10) | −0.0201 (11) |
C5 | 0.0610 (12) | 0.0801 (15) | 0.0547 (12) | −0.0052 (11) | −0.0205 (10) | −0.0167 (11) |
C6 | 0.0556 (12) | 0.0829 (16) | 0.0626 (14) | −0.0059 (11) | −0.0189 (10) | −0.0188 (11) |
C7 | 0.0666 (13) | 0.0879 (16) | 0.0694 (14) | 0.0082 (11) | −0.0292 (11) | −0.0350 (13) |
C8 | 0.0971 (18) | 0.0810 (16) | 0.0936 (17) | 0.0197 (13) | −0.0550 (15) | −0.0348 (14) |
C9 | 0.0620 (13) | 0.0729 (15) | 0.0805 (15) | 0.0040 (11) | −0.0361 (11) | −0.0271 (12) |
C10 | 0.0557 (12) | 0.0735 (14) | 0.0847 (16) | 0.0001 (10) | −0.0331 (11) | −0.0207 (13) |
C11 | 0.0839 (16) | 0.0785 (15) | 0.0817 (17) | −0.0122 (13) | −0.0266 (13) | −0.0198 (14) |
C12 | 0.0975 (19) | 0.0939 (19) | 0.0826 (18) | −0.0181 (15) | −0.0234 (14) | −0.0186 (15) |
C13 | 0.0747 (16) | 0.091 (2) | 0.100 (2) | −0.0151 (14) | −0.0258 (15) | −0.0053 (16) |
C14 | 0.0670 (15) | 0.0727 (16) | 0.122 (2) | −0.0080 (12) | −0.0364 (15) | −0.0126 (17) |
C15 | 0.0641 (14) | 0.0800 (16) | 0.1026 (19) | 0.0009 (12) | −0.0378 (13) | −0.0295 (15) |
C16 | 0.0706 (14) | 0.0690 (13) | 0.0711 (14) | 0.0023 (11) | −0.0329 (11) | −0.0258 (11) |
C17 | 0.102 (2) | 0.126 (2) | 0.0788 (17) | −0.0064 (17) | −0.0436 (15) | −0.0298 (16) |
C18 | 0.162 (4) | 0.148 (3) | 0.099 (2) | −0.024 (3) | −0.084 (3) | −0.008 (2) |
C19 | 0.138 (3) | 0.108 (2) | 0.179 (4) | −0.003 (2) | −0.115 (3) | −0.010 (3) |
C20 | 0.086 (2) | 0.095 (2) | 0.170 (3) | 0.0129 (15) | −0.070 (2) | −0.034 (2) |
C21 | 0.0734 (16) | 0.0829 (16) | 0.1002 (18) | 0.0074 (13) | −0.0382 (14) | −0.0320 (14) |
C22 | 0.0857 (17) | 0.0686 (14) | 0.0720 (15) | −0.0042 (13) | −0.0323 (13) | −0.0219 (12) |
C23 | 0.0680 (14) | 0.0747 (15) | 0.0776 (15) | 0.0004 (12) | −0.0233 (12) | −0.0271 (13) |
C24 | 0.0617 (13) | 0.0707 (14) | 0.0664 (13) | −0.0042 (11) | −0.0116 (11) | −0.0228 (11) |
C25 | 0.0630 (13) | 0.0645 (13) | 0.0650 (13) | −0.0050 (11) | −0.0117 (11) | −0.0283 (11) |
C26 | 0.0662 (14) | 0.0768 (15) | 0.0767 (15) | −0.0091 (12) | −0.0088 (12) | −0.0271 (13) |
C27 | 0.0894 (18) | 0.0723 (15) | 0.0680 (14) | −0.0180 (13) | −0.0163 (13) | −0.0192 (12) |
C28 | 0.0555 (12) | 0.0711 (13) | 0.0764 (15) | 0.0022 (10) | −0.0221 (11) | −0.0373 (12) |
C29 | 0.0640 (13) | 0.0672 (13) | 0.0686 (14) | 0.0005 (10) | −0.0217 (11) | −0.0320 (11) |
C30 | 0.0701 (15) | 0.0704 (14) | 0.0755 (15) | 0.0000 (11) | −0.0237 (12) | −0.0278 (12) |
C31 | 0.0818 (16) | 0.0825 (16) | 0.0759 (16) | −0.0070 (14) | −0.0188 (13) | −0.0263 (14) |
C32 | 0.116 (2) | 0.0773 (16) | 0.0760 (16) | −0.0003 (16) | −0.0378 (17) | −0.0236 (13) |
C33 | 0.106 (2) | 0.0975 (19) | 0.0891 (19) | 0.0164 (16) | −0.0494 (17) | −0.0336 (16) |
C34 | 0.0730 (15) | 0.0934 (17) | 0.0843 (17) | 0.0107 (13) | −0.0322 (13) | −0.0382 (15) |
C35 | 0.0564 (13) | 0.0958 (17) | 0.0813 (16) | 0.0023 (12) | −0.0197 (11) | −0.0350 (14) |
C36 | 0.0489 (12) | 0.0797 (14) | 0.0820 (15) | −0.0059 (10) | −0.0095 (10) | −0.0345 (12) |
C37 | 0.0516 (12) | 0.0690 (13) | 0.0717 (14) | −0.0014 (10) | −0.0104 (10) | −0.0228 (11) |
C38 | 0.0560 (14) | 0.144 (2) | 0.0809 (17) | −0.0112 (15) | −0.0075 (12) | −0.0396 (16) |
C39 | 0.0759 (18) | 0.171 (3) | 0.0763 (19) | −0.007 (2) | 0.0050 (15) | −0.039 (2) |
C40 | 0.108 (2) | 0.099 (2) | 0.0742 (17) | 0.0076 (17) | −0.0209 (17) | −0.0322 (15) |
C41 | 0.107 (2) | 0.117 (2) | 0.130 (3) | −0.0128 (18) | −0.034 (2) | −0.068 (2) |
C42 | 0.0726 (16) | 0.121 (2) | 0.117 (2) | −0.0263 (15) | −0.0008 (15) | −0.0702 (19) |
O1—N1 | 1.232 (2) | C22—C27 | 1.386 (3) |
O2—N1 | 1.225 (2) | C23—C24 | 1.370 (3) |
O3—N4 | 1.243 (3) | C23—H23 | 0.9300 |
O4—N4 | 1.228 (3) | C24—C25 | 1.408 (3) |
N1—C1 | 1.443 (3) | C24—H24 | 0.9300 |
N2—C4 | 1.370 (3) | C25—C26 | 1.407 (3) |
N2—N3 | 1.384 (2) | C26—C27 | 1.369 (3) |
N2—C7 | 1.485 (3) | C26—H26 | 0.9300 |
N3—C9 | 1.293 (3) | C27—H27 | 0.9300 |
N4—C22 | 1.444 (3) | C28—C29 | 1.458 (3) |
N5—C25 | 1.360 (3) | C28—C35 | 1.500 (3) |
N5—N6 | 1.385 (2) | C29—C30 | 1.391 (3) |
N5—C36 | 1.481 (3) | C29—C34 | 1.392 (3) |
N6—C28 | 1.291 (3) | C30—C31 | 1.382 (3) |
C1—C6 | 1.382 (3) | C30—H30 | 0.9300 |
C1—C2 | 1.384 (3) | C31—C32 | 1.377 (4) |
C2—C3 | 1.361 (3) | C31—H31 | 0.9300 |
C2—H2 | 0.9300 | C32—C33 | 1.378 (4) |
C3—C4 | 1.404 (3) | C32—H32 | 0.9300 |
C3—H3 | 0.9300 | C33—C34 | 1.373 (4) |
C4—C5 | 1.404 (3) | C33—H33 | 0.9300 |
C5—C6 | 1.364 (3) | C34—H34 | 0.9300 |
C5—H5 | 0.9300 | C35—C36 | 1.528 (3) |
C6—H6 | 0.9300 | C35—H35A | 0.9700 |
C7—C16 | 1.506 (3) | C35—H35B | 0.9700 |
C7—C8 | 1.533 (3) | C36—C37 | 1.514 (3) |
C7—H7 | 0.9800 | C36—H36 | 0.9800 |
C8—C9 | 1.499 (3) | C37—C42 | 1.361 (3) |
C8—H8A | 0.9700 | C37—C38 | 1.368 (3) |
C8—H8B | 0.9700 | C38—C39 | 1.390 (4) |
C9—C10 | 1.460 (3) | C38—H38 | 0.9300 |
C10—C11 | 1.389 (3) | C39—C40 | 1.338 (4) |
C10—C15 | 1.399 (3) | C39—H39 | 0.9300 |
C11—C12 | 1.377 (3) | C40—C41 | 1.339 (4) |
C11—H11 | 0.9300 | C40—H40 | 0.9300 |
C12—C13 | 1.381 (4) | C41—C42 | 1.381 (4) |
C12—H12 | 0.9300 | C41—H41 | 0.9300 |
C13—C14 | 1.364 (4) | C42—H42 | 0.9300 |
C13—H13 | 0.9300 | O5—C44 | 1.322 (8) |
C14—C15 | 1.384 (4) | C43—C44 | 1.370 (6) |
C14—H14 | 0.9300 | C43—H43A | 0.9600 |
C15—H15 | 0.9300 | C43—H43B | 0.9600 |
C16—C17 | 1.368 (3) | C43—H43C | 0.9600 |
C16—C21 | 1.381 (3) | C44—C45 | 1.301 (7) |
C17—C18 | 1.405 (5) | C45—H45A | 0.9600 |
C17—H17 | 0.9300 | C45—H45B | 0.9600 |
C18—C19 | 1.357 (5) | C45—H45C | 0.9600 |
C18—H18 | 0.9300 | C43'—H43D | 0.9600 |
C19—C20 | 1.340 (5) | C43'—H43E | 0.9600 |
C19—H19 | 0.9300 | C43'—H43F | 0.9600 |
C20—C21 | 1.371 (4) | C45'—H45D | 0.9600 |
C20—H20 | 0.9300 | C45'—H45E | 0.9600 |
C21—H21 | 0.9300 | C45'—H45F | 0.9600 |
C22—C23 | 1.375 (3) | ||
O2—N1—O1 | 121.7 (2) | C20—C21—H21 | 119.6 |
O2—N1—C1 | 118.9 (2) | C16—C21—H21 | 119.6 |
O1—N1—C1 | 119.4 (2) | C23—C22—C27 | 121.1 (2) |
C4—N2—N3 | 120.48 (17) | C23—C22—N4 | 119.6 (2) |
C4—N2—C7 | 126.41 (18) | C27—C22—N4 | 119.3 (2) |
N3—N2—C7 | 113.08 (18) | C24—C23—C22 | 119.9 (2) |
C9—N3—N2 | 108.51 (18) | C24—C23—H23 | 120.0 |
O4—N4—O3 | 122.6 (3) | C22—C23—H23 | 120.0 |
O4—N4—C22 | 118.9 (3) | C23—C24—C25 | 120.4 (2) |
O3—N4—C22 | 118.5 (3) | C23—C24—H24 | 119.8 |
C25—N5—N6 | 120.40 (17) | C25—C24—H24 | 119.8 |
C25—N5—C36 | 126.21 (19) | N5—C25—C26 | 120.7 (2) |
N6—N5—C36 | 112.80 (18) | N5—C25—C24 | 121.0 (2) |
C28—N6—N5 | 108.71 (18) | C26—C25—C24 | 118.3 (2) |
C6—C1—C2 | 120.8 (2) | C27—C26—C25 | 120.7 (2) |
C6—C1—N1 | 119.5 (2) | C27—C26—H26 | 119.6 |
C2—C1—N1 | 119.6 (2) | C25—C26—H26 | 119.6 |
C3—C2—C1 | 119.7 (2) | C26—C27—C22 | 119.4 (2) |
C3—C2—H2 | 120.1 | C26—C27—H27 | 120.3 |
C1—C2—H2 | 120.1 | C22—C27—H27 | 120.3 |
C2—C3—C4 | 120.7 (2) | N6—C28—C29 | 122.13 (19) |
C2—C3—H3 | 119.6 | N6—C28—C35 | 113.3 (2) |
C4—C3—H3 | 119.6 | C29—C28—C35 | 124.5 (2) |
N2—C4—C5 | 121.1 (2) | C30—C29—C34 | 117.9 (2) |
N2—C4—C3 | 120.5 (2) | C30—C29—C28 | 122.0 (2) |
C5—C4—C3 | 118.4 (2) | C34—C29—C28 | 120.1 (2) |
C6—C5—C4 | 120.6 (2) | C31—C30—C29 | 120.7 (2) |
C6—C5—H5 | 119.7 | C31—C30—H30 | 119.7 |
C4—C5—H5 | 119.7 | C29—C30—H30 | 119.7 |
C5—C6—C1 | 119.7 (2) | C32—C31—C30 | 120.6 (2) |
C5—C6—H6 | 120.1 | C32—C31—H31 | 119.7 |
C1—C6—H6 | 120.1 | C30—C31—H31 | 119.7 |
N2—C7—C16 | 111.80 (17) | C31—C32—C33 | 119.2 (3) |
N2—C7—C8 | 100.80 (17) | C31—C32—H32 | 120.4 |
C16—C7—C8 | 114.08 (19) | C33—C32—H32 | 120.4 |
N2—C7—H7 | 109.9 | C34—C33—C32 | 120.6 (3) |
C16—C7—H7 | 109.9 | C34—C33—H33 | 119.7 |
C8—C7—H7 | 109.9 | C32—C33—H33 | 119.7 |
C9—C8—C7 | 103.65 (18) | C33—C34—C29 | 121.0 (2) |
C9—C8—H8A | 111.0 | C33—C34—H34 | 119.5 |
C7—C8—H8A | 111.0 | C29—C34—H34 | 119.5 |
C9—C8—H8B | 111.0 | C28—C35—C36 | 103.49 (18) |
C7—C8—H8B | 111.0 | C28—C35—H35A | 111.1 |
H8A—C8—H8B | 109.0 | C36—C35—H35A | 111.1 |
N3—C9—C10 | 121.7 (2) | C28—C35—H35B | 111.1 |
N3—C9—C8 | 113.2 (2) | C36—C35—H35B | 111.1 |
C10—C9—C8 | 125.1 (2) | H35A—C35—H35B | 109.0 |
C11—C10—C15 | 117.6 (2) | N5—C36—C37 | 112.48 (18) |
C11—C10—C9 | 121.8 (2) | N5—C36—C35 | 101.57 (17) |
C15—C10—C9 | 120.6 (2) | C37—C36—C35 | 114.18 (18) |
C12—C11—C10 | 121.1 (2) | N5—C36—H36 | 109.4 |
C12—C11—H11 | 119.4 | C37—C36—H36 | 109.4 |
C10—C11—H11 | 119.4 | C35—C36—H36 | 109.4 |
C11—C12—C13 | 120.5 (3) | C42—C37—C38 | 117.8 (2) |
C11—C12—H12 | 119.7 | C42—C37—C36 | 122.66 (19) |
C13—C12—H12 | 119.7 | C38—C37—C36 | 119.6 (2) |
C14—C13—C12 | 119.2 (3) | C37—C38—C39 | 119.8 (3) |
C14—C13—H13 | 120.4 | C37—C38—H38 | 120.1 |
C12—C13—H13 | 120.4 | C39—C38—H38 | 120.1 |
C13—C14—C15 | 120.9 (2) | C40—C39—C38 | 121.7 (3) |
C13—C14—H14 | 119.5 | C40—C39—H39 | 119.2 |
C15—C14—H14 | 119.5 | C38—C39—H39 | 119.2 |
C14—C15—C10 | 120.6 (2) | C39—C40—C41 | 118.6 (3) |
C14—C15—H15 | 119.7 | C39—C40—H40 | 120.7 |
C10—C15—H15 | 119.7 | C41—C40—H40 | 120.7 |
C17—C16—C21 | 118.6 (2) | C40—C41—C42 | 121.1 (3) |
C17—C16—C7 | 120.9 (2) | C40—C41—H41 | 119.4 |
C21—C16—C7 | 120.4 (2) | C42—C41—H41 | 119.4 |
C16—C17—C18 | 119.3 (3) | C37—C42—C41 | 120.9 (2) |
C16—C17—H17 | 120.3 | C37—C42—H42 | 119.5 |
C18—C17—H17 | 120.3 | C41—C42—H42 | 119.5 |
C19—C18—C17 | 120.6 (3) | C45—C44—O5 | 96.7 (8) |
C19—C18—H18 | 119.7 | C45—C44—C43 | 164.8 (10) |
C17—C18—H18 | 119.7 | O5—C44—C43 | 98.4 (6) |
C20—C19—C18 | 119.9 (3) | H43D—C43'—H43E | 109.5 |
C20—C19—H19 | 120.1 | H43D—C43'—H43F | 109.5 |
C18—C19—H19 | 120.1 | H43E—C43'—H43F | 109.5 |
C19—C20—C21 | 120.8 (3) | H45D—C45'—H45E | 109.5 |
C19—C20—H20 | 119.6 | H45D—C45'—H45F | 109.5 |
C21—C20—H20 | 119.6 | H45E—C45'—H45F | 109.5 |
C20—C21—C16 | 120.8 (3) | ||
C4—N2—N3—C9 | −177.39 (18) | C17—C16—C21—C20 | −0.6 (4) |
C7—N2—N3—C9 | 4.6 (2) | C7—C16—C21—C20 | −179.5 (2) |
C25—N5—N6—C28 | 169.44 (17) | O4—N4—C22—C23 | −6.4 (3) |
C36—N5—N6—C28 | −2.3 (2) | O3—N4—C22—C23 | 175.4 (2) |
O2—N1—C1—C6 | −172.7 (2) | O4—N4—C22—C27 | 174.0 (2) |
O1—N1—C1—C6 | 6.0 (3) | O3—N4—C22—C27 | −4.3 (3) |
O2—N1—C1—C2 | 8.4 (3) | C27—C22—C23—C24 | −1.1 (3) |
O1—N1—C1—C2 | −172.82 (19) | N4—C22—C23—C24 | 179.3 (2) |
C6—C1—C2—C3 | 0.4 (3) | C22—C23—C24—C25 | 0.2 (3) |
N1—C1—C2—C3 | 179.28 (19) | N6—N5—C25—C26 | −169.88 (17) |
C1—C2—C3—C4 | −0.5 (3) | C36—N5—C25—C26 | 0.6 (3) |
N3—N2—C4—C5 | −1.6 (3) | N6—N5—C25—C24 | 9.9 (3) |
C7—N2—C4—C5 | 176.13 (18) | C36—N5—C25—C24 | −179.60 (18) |
N3—N2—C4—C3 | 178.39 (18) | C23—C24—C25—N5 | −178.91 (19) |
C7—N2—C4—C3 | −3.9 (3) | C23—C24—C25—C26 | 0.9 (3) |
C2—C3—C4—N2 | −179.22 (19) | N5—C25—C26—C27 | 178.60 (19) |
C2—C3—C4—C5 | 0.8 (3) | C24—C25—C26—C27 | −1.2 (3) |
N2—C4—C5—C6 | 178.89 (19) | C25—C26—C27—C22 | 0.4 (3) |
C3—C4—C5—C6 | −1.1 (3) | C23—C22—C27—C26 | 0.8 (3) |
C4—C5—C6—C1 | 1.1 (3) | N4—C22—C27—C26 | −179.6 (2) |
C2—C1—C6—C5 | −0.8 (3) | N5—N6—C28—C29 | −178.97 (17) |
N1—C1—C6—C5 | −179.61 (18) | N5—N6—C28—C35 | 0.3 (2) |
C4—N2—C7—C16 | −64.4 (3) | N6—C28—C29—C30 | −3.5 (3) |
N3—N2—C7—C16 | 113.5 (2) | C35—C28—C29—C30 | 177.41 (18) |
C4—N2—C7—C8 | 174.0 (2) | N6—C28—C29—C34 | 175.92 (19) |
N3—N2—C7—C8 | −8.1 (2) | C35—C28—C29—C34 | −3.2 (3) |
N2—C7—C8—C9 | 8.0 (2) | C34—C29—C30—C31 | −0.1 (3) |
C16—C7—C8—C9 | −112.0 (2) | C28—C29—C30—C31 | 179.27 (18) |
N2—N3—C9—C10 | −179.10 (17) | C29—C30—C31—C32 | 0.5 (3) |
N2—N3—C9—C8 | 1.4 (2) | C30—C31—C32—C33 | −0.6 (3) |
C7—C8—C9—N3 | −6.4 (2) | C31—C32—C33—C34 | 0.3 (4) |
C7—C8—C9—C10 | 174.16 (19) | C32—C33—C34—C29 | 0.1 (4) |
N3—C9—C10—C11 | −0.2 (3) | C30—C29—C34—C33 | −0.2 (3) |
C8—C9—C10—C11 | 179.2 (2) | C28—C29—C34—C33 | −179.6 (2) |
N3—C9—C10—C15 | 179.84 (19) | N6—C28—C35—C36 | 1.7 (2) |
C8—C9—C10—C15 | −0.8 (3) | C29—C28—C35—C36 | −179.12 (18) |
C15—C10—C11—C12 | 0.4 (3) | C25—N5—C36—C37 | 69.5 (3) |
C9—C10—C11—C12 | −179.5 (2) | N6—N5—C36—C37 | −119.35 (19) |
C10—C11—C12—C13 | 0.4 (4) | C25—N5—C36—C35 | −167.99 (19) |
C11—C12—C13—C14 | −0.7 (4) | N6—N5—C36—C35 | 3.1 (2) |
C12—C13—C14—C15 | 0.2 (4) | C28—C35—C36—N5 | −2.7 (2) |
C13—C14—C15—C10 | 0.6 (4) | C28—C35—C36—C37 | 118.63 (18) |
C11—C10—C15—C14 | −0.9 (3) | N5—C36—C37—C42 | 27.5 (3) |
C9—C10—C15—C14 | 179.0 (2) | C35—C36—C37—C42 | −87.5 (3) |
N2—C7—C16—C17 | 131.3 (2) | N5—C36—C37—C38 | −153.7 (2) |
C8—C7—C16—C17 | −115.1 (3) | C35—C36—C37—C38 | 91.3 (3) |
N2—C7—C16—C21 | −49.8 (3) | C42—C37—C38—C39 | 1.6 (4) |
C8—C7—C16—C21 | 63.8 (3) | C36—C37—C38—C39 | −177.3 (3) |
C21—C16—C17—C18 | 0.7 (4) | C37—C38—C39—C40 | −0.7 (5) |
C7—C16—C17—C18 | 179.6 (3) | C38—C39—C40—C41 | −0.5 (5) |
C16—C17—C18—C19 | −0.1 (5) | C39—C40—C41—C42 | 0.7 (5) |
C17—C18—C19—C20 | −0.6 (6) | C38—C37—C42—C41 | −1.4 (4) |
C18—C19—C20—C21 | 0.7 (5) | C36—C37—C42—C41 | 177.4 (3) |
C19—C20—C21—C16 | 0.0 (4) | C40—C41—C42—C37 | 0.2 (5) |