organic compounds
2-Hydroxy-8-phenyltricyclo[7.3.1.02,7]tridecan-13-one reacts with 2-aminobenzyl alcohol to form the title compound, C26H29NO, which crystallizes with two independent molecules in the asymmetric unit. The N atom shows a nearly planar coordination owing to the strain imposed on the fused-ring compound.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806005472/bt2011sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806005472/bt2011Isup2.hkl |
CCDC reference: 601119
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.002 Å
- R factor = 0.046
- wR factor = 0.133
- Data-to-parameter ratio = 18.5
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C10
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 1 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.
11-Phenyl-7,8,9,10,10a,11,12,13,14,15-decaydro-5H-3,1-benzoxazino[2,1-e]acridine top
Crystal data top
C26H29NO | Z = 4 |
Mr = 371.50 | F(000) = 800 |
Triclinic, P1 | Dx = 1.211 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.653 (1) Å | Cell parameters from 956 reflections |
b = 11.427 (1) Å | θ = 2.4–27.6° |
c = 17.337 (2) Å | µ = 0.07 mm−1 |
α = 91.124 (2)° | T = 295 K |
β = 100.810 (2)° | Prism, colorless |
γ = 100.191 (2)° | 0.40 × 0.35 × 0.25 mm |
V = 2037.4 (4) Å3 |
Data collection top
Bruker SMART 1000 CCD area-detector diffractometer | 6699 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.033 |
Graphite monochromator | θmax = 27.5°, θmin = 2.0° |
Detector resolution: 8.33 pixels mm-1 | h = −13→13 |
φ and ω scans | k = −14→14 |
25549 measured reflections | l = −22→22 |
9331 independent reflections |
Refinement top
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)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.133 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0534P)2 + 0.6554P] where P = (Fo2 + 2Fc2)/3 |
9331 reflections | (Δ/σ)max = 0.001 |
505 parameters | Δρmax = 0.49 e Å−3 |
0 restraints | Δρmin = −0.28 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
O1 | 0.4373 (1) | 0.8526 (1) | 0.3996 (1) | 0.0411 (3) | |
O2 | 0.4923 (1) | 0.3376 (1) | 0.0851 (1) | 0.0403 (2) | |
N1 | 0.6470 (1) | 0.8029 (1) | 0.4069 (1) | 0.0381 (3) | |
N2 | 0.7213 (1) | 0.3528 (1) | 0.1259 (1) | 0.0355 (3) | |
C1 | 0.4363 (2) | 0.8574 (2) | 0.3168 (1) | 0.0416 (3) | |
C2 | 0.5644 (2) | 0.9261 (1) | 0.3069 (1) | 0.0372 (3) | |
C3 | 0.5818 (2) | 1.0165 (2) | 0.2563 (1) | 0.0458 (4) | |
C4 | 0.7045 (2) | 1.0807 (2) | 0.2553 (1) | 0.0552 (4) | |
C5 | 0.8094 (2) | 1.0561 (2) | 0.3082 (1) | 0.0561 (4) | |
C6 | 0.7938 (2) | 0.9683 (2) | 0.3614 (1) | 0.0465 (4) | |
C7 | 0.6713 (1) | 0.8995 (1) | 0.3596 (1) | 0.0368 (3) | |
C8 | 0.7535 (1) | 0.7594 (1) | 0.4522 (1) | 0.0380 (3) | |
C9 | 0.8404 (2) | 0.7106 (2) | 0.4049 (1) | 0.0502 (4) | |
C10 | 0.9685 (2) | 0.6987 (2) | 0.4557 (1) | 0.0732 (6) | |
C11 | 0.9516 (2) | 0.6382 (2) | 0.5289 (1) | 0.0643 (5) | |
C12 | 0.8738 (2) | 0.6972 (2) | 0.5772 (1) | 0.0471 (4) | |
C13 | 0.7663 (1) | 0.7511 (1) | 0.5296 (1) | 0.0353 (3) | |
C14 | 0.6715 (1) | 0.7889 (1) | 0.5759 (1) | 0.0339 (3) | |
C15 | 0.7421 (1) | 0.8772 (1) | 0.6435 (1) | 0.0366 (3) | |
C16 | 0.8169 (2) | 0.9839 (2) | 0.6293 (1) | 0.0517 (4) | |
C17 | 0.8853 (2) | 1.0628 (2) | 0.6904 (1) | 0.0672 (6) | |
C18 | 0.8814 (2) | 1.0369 (2) | 0.7667 (1) | 0.0710 (6) | |
C19 | 0.8069 (2) | 0.9330 (2) | 0.7821 (1) | 0.0731 (7) | |
C20 | 0.7368 (2) | 0.8532 (2) | 0.7206 (1) | 0.0551 (5) | |
C21 | 0.5572 (1) | 0.8365 (1) | 0.5256 (1) | 0.0348 (3) | |
C22 | 0.4347 (2) | 0.8117 (2) | 0.5619 (1) | 0.0484 (4) | |
C23 | 0.3706 (2) | 0.6807 (2) | 0.5540 (1) | 0.0579 (5) | |
C24 | 0.3427 (2) | 0.6316 (2) | 0.4689 (1) | 0.0561 (5) | |
C25 | 0.4649 (2) | 0.6532 (1) | 0.4336 (1) | 0.0440 (4) | |
C26 | 0.5268 (1) | 0.7853 (1) | 0.4404 (1) | 0.0345 (3) | |
C27 | 0.4948 (2) | 0.2136 (1) | 0.0716 (1) | 0.0432 (4) | |
C28 | 0.5995 (2) | 0.2075 (1) | 0.0264 (1) | 0.0382 (3) | |
C29 | 0.5858 (2) | 0.1387 (2) | −0.0427 (1) | 0.0487 (4) | |
C30 | 0.6863 (2) | 0.1492 (2) | −0.0837 (1) | 0.0599 (5) | |
C31 | 0.7982 (2) | 0.2312 (2) | −0.0570 (1) | 0.0589 (5) | |
C32 | 0.8131 (2) | 0.3026 (2) | 0.0108 (1) | 0.0471 (4) | |
C33 | 0.7144 (1) | 0.2890 (1) | 0.0542 (1) | 0.0355 (3) | |
C34 | 0.8430 (1) | 0.4232 (1) | 0.1625 (1) | 0.0361 (3) | |
C35 | 0.9496 (2) | 0.3537 (2) | 0.1910 (1) | 0.0482 (4) | |
C36 | 1.0825 (2) | 0.4332 (2) | 0.2084 (1) | 0.0597 (5) | |
C37 | 1.0802 (2) | 0.5395 (2) | 0.2611 (1) | 0.0607 (5) | |
C38 | 0.9826 (2) | 0.6132 (2) | 0.2222 (1) | 0.0466 (4) | |
C39 | 0.8568 (1) | 0.5404 (1) | 0.1771 (1) | 0.0358 (3) | |
C40 | 0.7463 (1) | 0.6084 (1) | 0.1546 (1) | 0.0348 (3) | |
C41 | 0.7844 (1) | 0.7158 (1) | 0.1075 (1) | 0.0398 (3) | |
C42 | 0.8297 (2) | 0.7019 (2) | 0.0387 (1) | 0.0542 (4) | |
C43 | 0.8641 (2) | 0.7992 (2) | −0.0048 (1) | 0.0684 (6) | |
C44 | 0.8522 (2) | 0.9110 (2) | 0.0198 (1) | 0.0693 (6) | |
C45 | 0.8069 (2) | 0.9264 (2) | 0.0875 (1) | 0.0654 (6) | |
C46 | 0.7732 (2) | 0.8293 (2) | 0.1318 (1) | 0.0510 (4) | |
C47 | 0.6178 (1) | 0.5304 (1) | 0.1109 (1) | 0.0336 (3) | |
C48 | 0.4991 (2) | 0.5829 (1) | 0.1228 (1) | 0.0418 (3) | |
C49 | 0.4738 (2) | 0.5717 (2) | 0.2064 (1) | 0.0482 (4) | |
C50 | 0.4654 (2) | 0.4442 (2) | 0.2314 (1) | 0.0484 (4) | |
C51 | 0.5852 (2) | 0.3931 (1) | 0.2215 (1) | 0.0404 (3) | |
C52 | 0.6047 (1) | 0.4020 (1) | 0.1363 (1) | 0.0334 (3) | |
H1a | 0.3666 | 0.8961 | 0.2916 | 0.050* | |
H1b | 0.4228 | 0.7775 | 0.2930 | 0.050* | |
H3 | 0.5101 | 1.0346 | 0.2224 | 0.055* | |
H4 | 0.7160 | 1.1395 | 0.2196 | 0.066* | |
H5 | 0.8921 | 1.0993 | 0.3082 | 0.067* | |
H6 | 0.8649 | 0.9553 | 0.3982 | 0.056* | |
H9a | 0.7966 | 0.6332 | 0.3808 | 0.060* | |
H9b | 0.8563 | 0.7632 | 0.3632 | 0.060* | |
H10a | 1.0146 | 0.6539 | 0.4260 | 0.088* | |
H10b | 1.0212 | 0.7773 | 0.4693 | 0.088* | |
H11a | 1.0366 | 0.6369 | 0.5606 | 0.077* | |
H11b | 0.9084 | 0.5563 | 0.5153 | 0.077* | |
H12a | 0.9325 | 0.7593 | 0.6118 | 0.057* | |
H12b | 0.8358 | 0.6386 | 0.6100 | 0.057* | |
H14 | 0.6332 | 0.7174 | 0.5996 | 0.041* | |
H16 | 0.8209 | 1.0026 | 0.5778 | 0.062* | |
H17 | 0.9345 | 1.1340 | 0.6796 | 0.081* | |
H18 | 0.9290 | 1.0895 | 0.8077 | 0.085* | |
H19 | 0.8029 | 0.9153 | 0.8338 | 0.088* | |
H20 | 0.6860 | 0.7830 | 0.7317 | 0.066* | |
H21 | 0.5831 | 0.9230 | 0.5247 | 0.042* | |
H22a | 0.4578 | 0.8375 | 0.6171 | 0.058* | |
H22b | 0.3726 | 0.8583 | 0.5363 | 0.058* | |
H23a | 0.2899 | 0.6715 | 0.5733 | 0.069* | |
H23b | 0.4273 | 0.6353 | 0.5861 | 0.069* | |
H24a | 0.3089 | 0.5467 | 0.4667 | 0.067* | |
H24b | 0.2769 | 0.6694 | 0.4380 | 0.067* | |
H25a | 0.4430 | 0.6255 | 0.3787 | 0.053* | |
H25b | 0.5271 | 0.6079 | 0.4607 | 0.053* | |
H27a | 0.4116 | 0.1728 | 0.0419 | 0.052* | |
H27b | 0.5128 | 0.1762 | 0.1212 | 0.052* | |
H29 | 0.5087 | 0.0854 | −0.0614 | 0.058* | |
H30 | 0.6784 | 0.1013 | −0.1289 | 0.072* | |
H31 | 0.8653 | 0.2388 | −0.0850 | 0.071* | |
H32 | 0.8884 | 0.3591 | 0.0272 | 0.056* | |
H35a | 0.9484 | 0.2924 | 0.1511 | 0.058* | |
H35b | 0.9332 | 0.3147 | 0.2382 | 0.058* | |
H36a | 1.1466 | 0.3886 | 0.2340 | 0.072* | |
H36b | 1.1068 | 0.4601 | 0.1596 | 0.072* | |
H37a | 1.1661 | 0.5888 | 0.2731 | 0.073* | |
H37b | 1.0574 | 0.5122 | 0.3102 | 0.073* | |
H38a | 0.9628 | 0.6633 | 0.2624 | 0.056* | |
H38b | 1.0225 | 0.6651 | 0.1864 | 0.056* | |
H40 | 0.7287 | 0.6395 | 0.2038 | 0.042* | |
H42 | 0.8372 | 0.6264 | 0.0213 | 0.065* | |
H43 | 0.8951 | 0.7886 | −0.0507 | 0.082* | |
H44 | 0.8748 | 0.9761 | −0.0094 | 0.083* | |
H45 | 0.7985 | 1.0020 | 0.1041 | 0.078* | |
H46 | 0.7431 | 0.8407 | 0.1779 | 0.061* | |
H47 | 0.6194 | 0.5289 | 0.0546 | 0.040* | |
H48a | 0.5129 | 0.6663 | 0.1111 | 0.050* | |
H48b | 0.4230 | 0.5422 | 0.0861 | 0.050* | |
H49a | 0.5432 | 0.6231 | 0.2424 | 0.058* | |
H49b | 0.3930 | 0.5980 | 0.2092 | 0.058* | |
H50a | 0.3884 | 0.3949 | 0.2002 | 0.058* | |
H50b | 0.4567 | 0.4419 | 0.2861 | 0.058* | |
H51a | 0.5741 | 0.3104 | 0.2351 | 0.048* | |
H51b | 0.6615 | 0.4369 | 0.2567 | 0.048* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0355 (5) | 0.0538 (6) | 0.0381 (6) | 0.0193 (5) | 0.0073 (4) | 0.0061 (5) |
O2 | 0.0305 (5) | 0.0399 (6) | 0.0482 (6) | 0.0071 (4) | 0.0016 (4) | −0.0038 (5) |
N1 | 0.0338 (6) | 0.0470 (7) | 0.0386 (7) | 0.0169 (5) | 0.0103 (5) | 0.0089 (6) |
N2 | 0.0292 (6) | 0.0370 (6) | 0.0393 (7) | 0.0080 (5) | 0.0030 (5) | −0.0026 (5) |
C1 | 0.037 (1) | 0.051 (1) | 0.037 (1) | 0.014 (1) | 0.002 (1) | 0.003 (1) |
C2 | 0.040 (1) | 0.040 (1) | 0.033 (1) | 0.013 (1) | 0.006 (1) | 0.000 (1) |
C3 | 0.050 (1) | 0.048 (1) | 0.041 (1) | 0.018 (1) | 0.007 (1) | 0.007 (1) |
C4 | 0.061 (1) | 0.047 (1) | 0.062 (1) | 0.014 (1) | 0.017 (1) | 0.016 (1) |
C5 | 0.048 (1) | 0.051 (1) | 0.069 (1) | 0.002 (1) | 0.015 (1) | 0.009 (1) |
C6 | 0.038 (1) | 0.051 (1) | 0.050 (1) | 0.011 (1) | 0.005 (1) | 0.004 (1) |
C7 | 0.038 (1) | 0.040 (1) | 0.035 (1) | 0.012 (1) | 0.008 (1) | 0.001 (1) |
C8 | 0.034 (1) | 0.040 (1) | 0.043 (1) | 0.014 (1) | 0.009 (1) | 0.004 (1) |
C9 | 0.048 (1) | 0.059 (1) | 0.052 (1) | 0.026 (1) | 0.017 (1) | 0.005 (1) |
C10 | 0.056 (1) | 0.100 (2) | 0.078 (1) | 0.044 (1) | 0.022 (1) | 0.017 (1) |
C11 | 0.054 (1) | 0.077 (1) | 0.071 (1) | 0.039 (1) | 0.010 (1) | 0.013 (1) |
C12 | 0.045 (1) | 0.048 (1) | 0.048 (1) | 0.019 (1) | −0.002 (1) | 0.000 (1) |
C13 | 0.034 (1) | 0.031 (1) | 0.040 (1) | 0.009 (1) | 0.003 (1) | 0.000 (1) |
C14 | 0.035 (1) | 0.031 (1) | 0.035 (1) | 0.005 (1) | 0.006 (1) | 0.001 (1) |
C15 | 0.034 (1) | 0.038 (1) | 0.038 (1) | 0.009 (1) | 0.004 (1) | −0.002 (1) |
C16 | 0.047 (1) | 0.049 (1) | 0.057 (1) | −0.005 (1) | 0.019 (1) | −0.012 (1) |
C17 | 0.044 (1) | 0.063 (1) | 0.090 (2) | −0.008 (1) | 0.020 (1) | −0.032 (1) |
C18 | 0.050 (1) | 0.079 (2) | 0.075 (2) | 0.021 (1) | −0.016 (1) | −0.037 (1) |
C19 | 0.102 (2) | 0.081 (2) | 0.036 (1) | 0.044 (1) | −0.009 (1) | −0.008 (1) |
C20 | 0.077 (1) | 0.049 (1) | 0.040 (1) | 0.018 (1) | 0.006 (1) | 0.005 (1) |
C21 | 0.034 (1) | 0.034 (1) | 0.037 (1) | 0.008 (1) | 0.006 (1) | −0.002 (1) |
C22 | 0.040 (1) | 0.066 (1) | 0.042 (1) | 0.014 (1) | 0.011 (1) | −0.006 (1) |
C23 | 0.040 (1) | 0.078 (1) | 0.054 (1) | −0.002 (1) | 0.017 (1) | 0.007 (1) |
C24 | 0.044 (1) | 0.055 (1) | 0.062 (1) | −0.008 (1) | 0.007 (1) | −0.001 (1) |
C25 | 0.045 (1) | 0.042 (1) | 0.043 (1) | 0.006 (1) | 0.004 (1) | −0.005 (1) |
C26 | 0.031 (1) | 0.040 (1) | 0.035 (1) | 0.012 (1) | 0.006 (1) | 0.002 (1) |
C27 | 0.039 (1) | 0.036 (1) | 0.051 (1) | 0.002 (1) | 0.004 (1) | 0.001 (1) |
C28 | 0.039 (1) | 0.032 (1) | 0.043 (1) | 0.010 (1) | 0.002 (1) | 0.003 (1) |
C29 | 0.050 (1) | 0.041 (1) | 0.052 (1) | 0.014 (1) | −0.003 (1) | −0.005 (1) |
C30 | 0.065 (1) | 0.067 (1) | 0.048 (1) | 0.025 (1) | 0.003 (1) | −0.016 (1) |
C31 | 0.057 (1) | 0.076 (1) | 0.050 (1) | 0.023 (1) | 0.018 (1) | −0.004 (1) |
C32 | 0.040 (1) | 0.054 (1) | 0.049 (1) | 0.011 (1) | 0.011 (1) | 0.000 (1) |
C33 | 0.036 (1) | 0.034 (1) | 0.038 (1) | 0.012 (1) | 0.005 (1) | 0.003 (1) |
C34 | 0.031 (1) | 0.040 (1) | 0.037 (1) | 0.007 (1) | 0.003 (1) | 0.002 (1) |
C35 | 0.038 (1) | 0.050 (1) | 0.055 (1) | 0.015 (1) | −0.002 (1) | 0.002 (1) |
C36 | 0.035 (1) | 0.070 (1) | 0.071 (1) | 0.015 (1) | −0.002 (1) | 0.002 (1) |
C37 | 0.042 (1) | 0.065 (1) | 0.064 (1) | 0.006 (1) | −0.012 (1) | 0.000 (1) |
C38 | 0.041 (1) | 0.047 (1) | 0.046 (1) | 0.000 (1) | −0.001 (1) | 0.003 (1) |
C39 | 0.033 (1) | 0.039 (1) | 0.033 (1) | 0.004 (1) | 0.003 (1) | 0.005 (1) |
C40 | 0.037 (1) | 0.034 (1) | 0.034 (1) | 0.006 (1) | 0.006 (1) | 0.003 (1) |
C41 | 0.033 (1) | 0.039 (1) | 0.046 (1) | 0.006 (1) | 0.004 (1) | 0.010 (1) |
C42 | 0.053 (1) | 0.059 (1) | 0.060 (1) | 0.021 (1) | 0.021 (1) | 0.022 (1) |
C43 | 0.050 (1) | 0.091 (2) | 0.075 (1) | 0.023 (1) | 0.026 (1) | 0.045 (1) |
C44 | 0.040 (1) | 0.066 (1) | 0.095 (2) | −0.001 (1) | 0.003 (1) | 0.045 (1) |
C45 | 0.056 (1) | 0.038 (1) | 0.090 (2) | −0.001 (1) | −0.009 (1) | 0.015 (1) |
C46 | 0.051 (1) | 0.039 (1) | 0.058 (1) | 0.004 (1) | 0.000 (1) | 0.004 (1) |
C47 | 0.034 (1) | 0.037 (1) | 0.031 (1) | 0.009 (1) | 0.006 (1) | 0.006 (1) |
C48 | 0.039 (1) | 0.040 (1) | 0.048 (1) | 0.014 (1) | 0.007 (1) | 0.007 (1) |
C49 | 0.045 (1) | 0.051 (1) | 0.054 (1) | 0.017 (1) | 0.017 (1) | −0.001 (1) |
C50 | 0.051 (1) | 0.056 (1) | 0.045 (1) | 0.013 (1) | 0.022 (1) | 0.008 (1) |
C51 | 0.044 (1) | 0.040 (1) | 0.040 (1) | 0.009 (1) | 0.011 (1) | 0.009 (1) |
C52 | 0.029 (1) | 0.035 (1) | 0.036 (7) | 0.007 (1) | 0.005 (1) | 0.001 (1) |
Geometric parameters (Å, º) top
O1—C26 | 1.424 (2) | C48—C49 | 1.526 (2) |
O1—C1 | 1.436 (2) | C49—C50 | 1.521 (2) |
O2—C52 | 1.423 (2) | C50—C51 | 1.530 (2) |
O2—C27 | 1.438 (2) | C51—C52 | 1.533 (2) |
N1—C7 | 1.404 (2) | C1—H1a | 0.97 |
N1—C8 | 1.425 (2) | C1—H1b | 0.97 |
N1—C26 | 1.487 (2) | C3—H3 | 0.93 |
N2—C33 | 1.413 (2) | C4—H4 | 0.93 |
N2—C34 | 1.426 (2) | C5—H5 | 0.93 |
N2—C52 | 1.489 (2) | C6—H6 | 0.93 |
C1—C2 | 1.490 (2) | C9—H9a | 0.97 |
C2—C3 | 1.378 (2) | C9—H9b | 0.97 |
C2—C7 | 1.403 (2) | C10—H10a | 0.97 |
C3—C4 | 1.385 (2) | C10—H10b | 0.97 |
C4—C5 | 1.381 (3) | C11—H11a | 0.97 |
C5—C6 | 1.385 (2) | C11—H11b | 0.97 |
C6—C7 | 1.394 (2) | C12—H12a | 0.97 |
C8—C13 | 1.331 (2) | C12—H12b | 0.97 |
C8—C9 | 1.514 (2) | C14—H14 | 0.98 |
C9—C10 | 1.509 (3) | C16—H16 | 0.93 |
C10—C11 | 1.483 (3) | C17—H17 | 0.93 |
C11—C12 | 1.509 (2) | C18—H18 | 0.93 |
C12—C13 | 1.511 (2) | C19—H19 | 0.93 |
C13—C14 | 1.514 (2) | C20—H20 | 0.93 |
C14—C15 | 1.521 (2) | C21—H21 | 0.98 |
C14—C21 | 1.547 (2) | C22—H22a | 0.97 |
C15—C20 | 1.379 (2) | C22—H22b | 0.97 |
C15—C16 | 1.386 (2) | C23—H23a | 0.97 |
C16—C17 | 1.381 (3) | C23—H23b | 0.97 |
C17—C18 | 1.368 (3) | C24—H24a | 0.97 |
C18—C19 | 1.368 (3) | C24—H24b | 0.97 |
C19—C20 | 1.396 (3) | C25—H25a | 0.97 |
C21—C26 | 1.533 (2) | C25—H25b | 0.97 |
C21—C22 | 1.537 (2) | C27—H27a | 0.97 |
C22—C23 | 1.523 (3) | C27—H27b | 0.97 |
C23—C24 | 1.524 (3) | C29—H29 | 0.93 |
C24—C25 | 1.523 (2) | C30—H30 | 0.93 |
C25—C26 | 1.529 (2) | C31—H31 | 0.93 |
C27—C28 | 1.489 (2) | C32—H32 | 0.93 |
C28—C29 | 1.389 (2) | C35—H35a | 0.97 |
C28—C33 | 1.398 (2) | C35—H35b | 0.97 |
C29—C30 | 1.382 (3) | C36—H36a | 0.97 |
C30—C31 | 1.376 (3) | C36—H36b | 0.97 |
C31—C32 | 1.385 (2) | C37—H37a | 0.97 |
C32—C33 | 1.392 (2) | C37—H37b | 0.97 |
C34—C39 | 1.335 (2) | C38—H38a | 0.97 |
C34—C35 | 1.513 (2) | C38—H38b | 0.97 |
C35—C36 | 1.514 (2) | C40—H40 | 0.98 |
C36—C37 | 1.513 (3) | C42—H42 | 0.93 |
C37—C38 | 1.522 (2) | C43—H43 | 0.93 |
C38—C39 | 1.511 (2) | C44—H44 | 0.93 |
C39—C40 | 1.518 (2) | C45—H45 | 0.93 |
C40—C41 | 1.525 (2) | C46—H46 | 0.93 |
C40—C47 | 1.548 (2) | C47—H47 | 0.98 |
C41—C42 | 1.385 (2) | C48—H48a | 0.97 |
C41—C46 | 1.388 (2) | C48—H48b | 0.97 |
C42—C43 | 1.390 (3) | C49—H49a | 0.97 |
C43—C44 | 1.374 (3) | C49—H49b | 0.97 |
C44—C45 | 1.369 (3) | C50—H50a | 0.97 |
C45—C46 | 1.394 (3) | C50—H50b | 0.97 |
C47—C52 | 1.530 (2) | C51—H51a | 0.97 |
C47—C48 | 1.536 (2) | C51—H51b | 0.97 |
C26—O1—C1 | 114.3 (1) | C11—C10—H10b | 109.1 |
C52—O2—C27 | 114.4 (1) | C9—C10—H10b | 109.1 |
C7—N1—C8 | 119.5 (1) | H10a—C10—H10b | 107.9 |
C7—N1—C26 | 119.0 (1) | C10—C11—H11a | 108.9 |
C8—N1—C26 | 115.0 (1) | C12—C11—H11a | 108.9 |
C33—N2—C34 | 118.3 (1) | C10—C11—H11b | 108.9 |
C33—N2—C52 | 117.3 (1) | C12—C11—H11b | 108.9 |
C34—N2—C52 | 115.2 (1) | H11a—C11—H11b | 107.7 |
O1—C1—C2 | 107.8 (1) | C11—C12—H12a | 108.6 |
C3—C2—C7 | 120.1 (2) | C13—C12—H12a | 108.6 |
C3—C2—C1 | 125.3 (1) | C11—C12—H12b | 108.6 |
C7—C2—C1 | 114.3 (1) | C13—C12—H12b | 108.6 |
C2—C3—C4 | 121.0 (2) | H12a—C12—H12b | 107.6 |
C5—C4—C3 | 118.9 (1) | C13—C14—H14 | 106.6 |
C4—C5—C6 | 121.2 (2) | C15—C14—H14 | 106.6 |
C5—C6—C7 | 119.9 (2) | C21—C14—H14 | 106.6 |
C6—C7—N1 | 124.2 (1) | C17—C16—H16 | 119.4 |
C6—C7—C2 | 118.8 (1) | C15—C16—H16 | 119.4 |
N1—C7—C2 | 116.9 (1) | C18—C17—H17 | 119.7 |
C13—C8—N1 | 121.7 (1) | C16—C17—H17 | 119.7 |
C13—C8—C9 | 122.8 (1) | C19—C18—H18 | 120.3 |
N1—C8—C9 | 115.1 (1) | C17—C18—H18 | 120.3 |
C10—C9—C8 | 111.6 (2) | C18—C19—H19 | 119.8 |
C11—C10—C9 | 112.3 (2) | C20—C19—H19 | 119.8 |
C10—C11—C12 | 113.3 (2) | C15—C20—H20 | 119.6 |
C11—C12—C13 | 114.7 (1) | C19—C20—H20 | 119.6 |
C8—C13—C12 | 122.0 (1) | C26—C21—H21 | 107.7 |
C8—C13—C14 | 122.8 (1) | C22—C21—H21 | 107.7 |
C12—C13—C14 | 115.2 (1) | C14—C21—H21 | 107.7 |
C13—C14—C15 | 110.9 (1) | C23—C22—H22a | 109.0 |
C13—C14—C21 | 114.6 (1) | C21—C22—H22a | 109.0 |
C15—C14—C21 | 111.1 (1) | C23—C22—H22b | 109.0 |
C20—C15—C16 | 117.8 (2) | C21—C22—H22b | 109.0 |
C20—C15—C14 | 121.5 (2) | H22a—C22—H22b | 107.8 |
C16—C15—C14 | 120.6 (1) | C22—C23—H23a | 109.3 |
C17—C16—C15 | 121.1 (2) | C24—C23—H23a | 109.3 |
C18—C17—C16 | 120.5 (2) | C22—C23—H23b | 109.3 |
C19—C18—C17 | 119.4 (2) | C24—C23—H23b | 109.3 |
C18—C19—C20 | 120.3 (2) | H23a—C23—H23b | 107.9 |
C15—C20—C19 | 120.8 (2) | C25—C24—H24a | 109.4 |
C26—C21—C22 | 110.3 (1) | C23—C24—H24a | 109.4 |
C26—C21—C14 | 111.9 (1) | C25—C24—H24b | 109.4 |
C22—C21—C14 | 111.5 (1) | C23—C24—H24b | 109.4 |
C23—C22—C21 | 113.0 (1) | H24a—C24—H24b | 108.0 |
C22—C23—C24 | 111.7 (2) | C24—C25—H25a | 109.4 |
C25—C24—C23 | 111.3 (1) | C26—C25—H25a | 109.4 |
C24—C25—C26 | 111.3 (1) | C24—C25—H25b | 109.4 |
O1—C26—N1 | 109.8 (1) | C26—C25—H25b | 109.4 |
O1—C26—C25 | 109.9 (1) | H25a—C25—H25b | 108.0 |
N1—C26—C25 | 109.9 (1) | O2—C27—H27a | 110.3 |
O1—C26—C21 | 104.8 (1) | C28—C27—H27a | 110.3 |
N1—C26—C21 | 110.2 (1) | O2—C27—H27b | 110.3 |
C25—C26—C21 | 112.1 (1) | C28—C27—H27b | 110.3 |
O2—C27—C28 | 106.9 (1) | H27a—C27—H27b | 108.6 |
C29—C28—C33 | 120.2 (2) | C30—C29—H29 | 119.9 |
C29—C28—C27 | 125.5 (1) | C28—C29—H29 | 119.9 |
C33—C28—C27 | 114.0 (1) | C31—C30—H30 | 120.3 |
C30—C29—C28 | 120.2 (2) | C29—C30—H30 | 120.3 |
C31—C30—C29 | 119.5 (2) | C30—C31—H31 | 119.3 |
C30—C31—C32 | 121.5 (2) | C32—C31—H31 | 119.3 |
C31—C32—C33 | 119.3 (2) | C31—C32—H32 | 120.3 |
C32—C33—C28 | 119.3 (1) | C33—C32—H32 | 120.3 |
C32—C33—N2 | 124.3 (1) | C34—C35—H35a | 109.3 |
C28—C33—N2 | 116.4 (1) | C36—C35—H35a | 109.3 |
C39—C34—N2 | 121.8 (1) | C34—C35—H35b | 109.3 |
C39—C34—C35 | 122.9 (1) | C36—C35—H35b | 109.3 |
N2—C34—C35 | 115.1 (1) | H35a—C35—H35b | 107.9 |
C34—C35—C36 | 111.8 (1) | C37—C36—H36a | 109.7 |
C37—C36—C35 | 109.9 (2) | C35—C36—H36a | 109.7 |
C36—C37—C38 | 111.3 (2) | C37—C36—H36b | 109.7 |
C39—C38—C37 | 114.3 (1) | C35—C36—H36b | 109.7 |
C34—C39—C38 | 121.7 (1) | H36a—C36—H36b | 108.2 |
C34—C39—C40 | 122.8 (1) | C36—C37—H37a | 109.4 |
C38—C39—C40 | 115.4 (1) | C38—C37—H37a | 109.4 |
C39—C40—C41 | 111.9 (1) | C36—C37—H37b | 109.4 |
C39—C40—C47 | 114.0 (1) | C38—C37—H37b | 109.4 |
C41—C40—C47 | 110.3 (1) | H37a—C37—H37b | 108.0 |
C42—C41—C46 | 118.4 (2) | C39—C38—H38a | 108.7 |
C42—C41—C40 | 120.5 (1) | C37—C38—H38a | 108.7 |
C46—C41—C40 | 121.1 (2) | C39—C38—H38b | 108.7 |
C41—C42—C43 | 120.9 (2) | C37—C38—H38b | 108.7 |
C44—C43—C42 | 120.1 (2) | H38a—C38—H38b | 107.6 |
C45—C44—C43 | 119.8 (2) | C39—C40—H40 | 106.7 |
C44—C45—C46 | 120.4 (2) | C41—C40—H40 | 106.7 |
C41—C46—C45 | 120.4 (2) | C47—C40—H40 | 106.7 |
C52—C47—C48 | 110.3 (1) | C41—C42—H42 | 119.5 |
C52—C47—C40 | 111.5 (1) | C43—C42—H42 | 119.5 |
C48—C47—C40 | 111.5 (1) | C44—C43—H43 | 120.0 |
C49—C48—C47 | 112.6 (1) | C42—C43—H43 | 120.0 |
C50—C49—C48 | 111.7 (1) | C45—C44—H44 | 120.1 |
C49—C50—C51 | 112.1 (1) | C43—C44—H44 | 120.1 |
C50—C51—C52 | 110.0 (1) | C44—C45—H45 | 119.8 |
O2—C52—N2 | 109.8 (1) | C46—C45—H45 | 119.8 |
O2—C52—C47 | 105.5 (1) | C41—C46—H46 | 119.8 |
N2—C52—C47 | 109.9 (1) | C45—C46—H46 | 119.8 |
O2—C52—C51 | 109.3 (1) | C52—C47—H47 | 107.8 |
N2—C52—C51 | 110.5 (1) | C48—C47—H47 | 107.8 |
C47—C52—C51 | 111.8 (1) | C40—C47—H47 | 107.8 |
O1—C1—H1a | 110.2 | C49—C48—H48a | 109.1 |
C2—C1—H1a | 110.2 | C47—C48—H48a | 109.1 |
O1—C1—H1b | 110.2 | C49—C48—H48b | 109.1 |
C2—C1—H1b | 110.2 | C47—C48—H48b | 109.1 |
H1a—C1—H1b | 108.5 | H48a—C48—H48b | 107.8 |
C2—C3—H3 | 119.5 | C50—C49—H49a | 109.3 |
C4—C3—H3 | 119.5 | C48—C49—H49a | 109.3 |
C5—C4—H4 | 120.6 | C50—C49—H49b | 109.3 |
C3—C4—H4 | 120.6 | C48—C49—H49b | 109.3 |
C4—C5—H5 | 119.4 | H49a—C49—H49b | 107.9 |
C6—C5—H5 | 119.4 | C49—C50—H50a | 109.2 |
C5—C6—H6 | 120.1 | C51—C50—H50a | 109.2 |
C7—C6—H6 | 120.1 | C49—C50—H50b | 109.2 |
C10—C9—H9a | 109.3 | C51—C50—H50b | 109.2 |
C8—C9—H9a | 109.3 | H50a—C50—H50b | 107.9 |
C10—C9—H9b | 109.3 | C50—C51—H51a | 109.7 |
C8—C9—H9b | 109.3 | C52—C51—H51a | 109.7 |
H9a—C9—H9b | 108.0 | C50—C51—H51b | 109.7 |
C11—C10—H10a | 109.1 | C52—C51—H51b | 109.7 |
C9—C10—H10a | 109.1 | H51a—C51—H51b | 108.2 |
C26—O1—C1—C2 | −66.6 (2) | C52—O2—C27—C28 | −67.2 (2) |
O1—C1—C2—C3 | −132.7 (2) | O2—C27—C28—C29 | −129.2 (2) |
O1—C1—C2—C7 | 41.7 (2) | O2—C27—C28—C33 | 43.9 (2) |
C7—C2—C3—C4 | 1.4 (2) | C33—C28—C29—C30 | 1.0 (2) |
C1—C2—C3—C4 | 175.5 (2) | C27—C28—C29—C30 | 173.6 (2) |
C2—C3—C4—C5 | −2.6 (3) | C28—C29—C30—C31 | −2.2 (3) |
C3—C4—C5—C6 | 0.5 (3) | C29—C30—C31—C32 | 0.8 (3) |
C4—C5—C6—C7 | 2.9 (3) | C30—C31—C32—C33 | 1.8 (3) |
C5—C6—C7—N1 | 175.1 (2) | C31—C32—C33—C28 | −3.1 (2) |
C5—C6—C7—C2 | −4.0 (2) | C31—C32—C33—N2 | 177.0 (2) |
C8—N1—C7—C6 | −9.2 (2) | C29—C28—C33—C32 | 1.7 (2) |
C26—N1—C7—C6 | 141.1 (2) | C27—C28—C33—C32 | −171.7 (1) |
C8—N1—C7—C2 | 170.0 (1) | C29—C28—C33—N2 | −178.3 (1) |
C26—N1—C7—C2 | −39.8 (2) | C27—C28—C33—N2 | 8.3 (2) |
C3—C2—C7—C6 | 2.0 (2) | C34—N2—C33—C32 | −9.3 (2) |
C1—C2—C7—C6 | −172.8 (1) | C52—N2—C33—C32 | 135.8 (2) |
C3—C2—C7—N1 | −177.2 (1) | C34—N2—C33—C28 | 170.7 (1) |
C1—C2—C7—N1 | 8.1 (2) | C52—N2—C33—C28 | −44.2 (2) |
C7—N1—C8—C13 | 124.5 (2) | C33—N2—C34—C39 | 120.8 (2) |
C26—N1—C8—C13 | −26.9 (2) | C52—N2—C34—C39 | −25.1 (2) |
C7—N1—C8—C9 | −62.4 (2) | C33—N2—C34—C35 | −65.6 (2) |
C26—N1—C8—C9 | 146.2 (1) | C52—N2—C34—C35 | 148.6 (1) |
C13—C8—C9—C10 | −22.9 (2) | C39—C34—C35—C36 | −21.9 (2) |
N1—C8—C9—C10 | 164.2 (2) | N2—C34—C35—C36 | 164.5 (1) |
C8—C9—C10—C11 | 48.3 (2) | C34—C35—C36—C37 | 50.6 (2) |
C9—C10—C11—C12 | −55.4 (3) | C35—C36—C37—C38 | −60.5 (2) |
C10—C11—C12—C13 | 34.6 (3) | C36—C37—C38—C39 | 39.9 (2) |
N1—C8—C13—C12 | 175.7 (1) | N2—C34—C39—C38 | 174.5 (1) |
C9—C8—C13—C12 | 3.1 (2) | C35—C34—C39—C38 | 1.4 (2) |
N1—C8—C13—C14 | −1.3 (2) | N2—C34—C39—C40 | −1.5 (2) |
C9—C8—C13—C14 | −173.8 (1) | C35—C34—C39—C40 | −174.6 (1) |
C11—C12—C13—C8 | −8.6 (2) | C37—C38—C39—C34 | −10.5 (2) |
C11—C12—C13—C14 | 168.6 (2) | C37—C38—C39—C40 | 165.8 (2) |
C8—C13—C14—C15 | −126.0 (2) | C34—C39—C40—C41 | −127.9 (2) |
C12—C13—C14—C15 | 56.9 (2) | C38—C39—C40—C41 | 55.8 (2) |
C8—C13—C14—C21 | 0.8 (2) | C34—C39—C40—C47 | −1.8 (2) |
C12—C13—C14—C21 | −176.3 (1) | C38—C39—C40—C47 | −178.1 (1) |
C13—C14—C15—C20 | −119.9 (2) | C39—C40—C41—C42 | 56.2 (2) |
C21—C14—C15—C20 | 111.4 (2) | C47—C40—C41—C42 | −71.9 (2) |
C13—C14—C15—C16 | 58.5 (2) | C39—C40—C41—C46 | −124.7 (2) |
C21—C14—C15—C16 | −70.2 (2) | C47—C40—C41—C46 | 107.3 (2) |
C20—C15—C16—C17 | 0.9 (3) | C46—C41—C42—C43 | 0.5 (3) |
C14—C15—C16—C17 | −177.6 (2) | C40—C41—C42—C43 | 179.7 (2) |
C15—C16—C17—C18 | 0.3 (3) | C41—C42—C43—C44 | −0.7 (3) |
C16—C17—C18—C19 | −1.2 (3) | C42—C43—C44—C45 | 0.2 (3) |
C17—C18—C19—C20 | 0.8 (3) | C43—C44—C45—C46 | 0.3 (3) |
C16—C15—C20—C19 | −1.3 (3) | C42—C41—C46—C45 | 0.0 (2) |
C14—C15—C20—C19 | 177.1 (2) | C40—C41—C46—C45 | −179.1 (2) |
C18—C19—C20—C15 | 0.5 (3) | C44—C45—C46—C41 | −0.4 (3) |
C13—C14—C21—C26 | 26.1 (2) | C39—C40—C47—C52 | 29.9 (2) |
C15—C14—C21—C26 | 152.8 (1) | C41—C40—C47—C52 | 156.9 (2) |
C13—C14—C21—C22 | 150.2 (1) | C39—C40—C47—C48 | 153.8 (1) |
C15—C14—C21—C22 | −83.2 (2) | C41—C40—C47—C48 | −79.3 (2) |
C26—C21—C22—C23 | 53.0 (2) | C52—C47—C48—C49 | 53.5 (2) |
C14—C21—C22—C23 | −72.0 (2) | C40—C47—C48—C49 | −71.0 (2) |
C21—C22—C23—C24 | −53.6 (2) | C47—C48—C49—C50 | −52.8 (2) |
C22—C23—C24—C25 | 54.2 (2) | C48—C49—C50—C51 | 54.0 (2) |
C23—C24—C25—C26 | −55.5 (2) | C49—C50—C51—C52 | −55.9 (2) |
C1—O1—C26—N1 | 36.7 (2) | C27—O2—C52—N2 | 33.3 (2) |
C1—O1—C26—C25 | −84.4 (2) | C27—O2—C52—C47 | 151.7 (1) |
C1—O1—C26—C21 | 155.1 (1) | C27—O2—C52—C51 | −88.0 (1) |
C7—N1—C26—O1 | 16.7 (2) | C33—N2—C52—O2 | 22.3 (2) |
C8—N1—C26—O1 | 168.2 (1) | C34—N2—C52—O2 | 168.5 (1) |
C7—N1—C26—C25 | 137.7 (1) | C33—N2—C52—C47 | −93.3 (1) |
C8—N1—C26—C25 | −70.8 (2) | C34—N2—C52—C47 | 52.9 (2) |
C7—N1—C26—C21 | −98.3 (2) | C33—N2—C52—C51 | 142.9 (1) |
C8—N1—C26—C21 | 53.2 (2) | C34—N2—C52—C51 | −70.9 (2) |
C24—C25—C26—O1 | −60.1 (2) | C48—C47—C52—O2 | 62.8 (1) |
C24—C25—C26—N1 | 178.9 (1) | C40—C47—C52—O2 | −172.8 (1) |
C24—C25—C26—C21 | 56.0 (2) | C48—C47—C52—N2 | −178.9 (1) |
C22—C21—C26—O1 | 65.3 (2) | C40—C47—C52—N2 | −54.4 (2) |
C14—C21—C26—O1 | −170.0 (1) | C48—C47—C52—C51 | −55.9 (2) |
C22—C21—C26—N1 | −176.6 (1) | C40—C47—C52—C51 | 68.6 (2) |
C14—C21—C26—N1 | −51.9 (2) | C50—C51—C52—O2 | −59.2 (2) |
C22—C21—C26—C25 | −53.9 (2) | C50—C51—C52—N2 | 179.9 (1) |
C14—C21—C26—C25 | 70.8 (2) | C50—C51—C52—C47 | 57.2 (2) |