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
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.004 Å
- Disorder in solvent or counterion
- R factor = 0.053
- wR factor = 0.180
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT413_ALERT_2_A Short Inter XH3 .. XHn H38 .. H43F .. 1.70 Ang.
Alert level B PLAT432_ALERT_2_B Short Inter X...Y Contact O4 .. C45' .. 2.89 Ang. PLAT432_ALERT_2_B Short Inter X...Y Contact C38 .. C43' .. 2.94 Ang.
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 0.50 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT202_ALERT_3_C Isotropic non-H Atoms in Anion/Solvent ......... 4 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C39 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C16 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C37 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C40 PLAT243_ALERT_4_C High 'Solvent' Ueq as Compared to Neighbors for C44 PLAT244_ALERT_4_C Low 'Solvent' Ueq as Compared to Neighbors for C44' PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 50.00 Perc. PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O5 PLAT309_ALERT_2_C Single Bonded Oxygen (C-O .GT. 1.3 Ang) ........ O5' PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C37 -C42 1.37 Ang. PLAT413_ALERT_2_C Short Inter XH3 .. XHn H12 .. H43D .. 2.12 Ang.
1 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 11 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion
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) |
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