Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014673/ob6248sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014673/ob6248Isup2.hkl |
CCDC reference: 221711
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.003 Å
- R factor = 0.052
- wR factor = 0.136
- Data-to-parameter ratio = 17.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N2 - H2 ... ?
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1991); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: TEXSAN and Mercury (Bruno et al., 2002); software used to prepare material for publication: TEXSAN and Mercury.
C46H36N2O3 | F(000) = 1400 |
Mr = 664.77 | Dx = 1.255 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71069 Å |
a = 13.910 (4) Å | Cell parameters from 19635 reflections |
b = 13.425 (4) Å | θ = 3.7–55° |
c = 19.074 (6) Å | µ = 0.08 mm−1 |
β = 99.074 (19)° | T = 296 K |
V = 3517.3 (18) Å3 | Prism, colorless |
Z = 4 | 0.10 × 0.10 × 0.10 mm |
Rigaku R-AXIS RAPID Imaging Plate diffractometer | 7998 independent reflections |
Radiation source: fine-focus sealed tube | 3722 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.075 |
Detector resolution: 10.00 pixels mm-1 | θmax = 27.5°, θmin = 2.1° |
ω scans | h = −18→16 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −17→17 |
Tmin = 0.992, Tmax = 0.992 | l = −24→24 |
34653 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) = 0.136 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.86 | w = 1/[σ2(Fo2) + (0.0697P)2] where P = (Fo2 + 2Fc2)/3 |
7998 reflections | (Δ/σ)max = 0.001 |
469 parameters | Δρmax = 0.16 e Å−3 |
0 restraints | Δρmin = −0.23 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 | ||
O1 | 0.11831 (11) | 0.77525 (13) | 0.82071 (10) | 0.0762 (5) | |
O2 | 0.33937 (12) | 0.37481 (12) | 1.03509 (8) | 0.0642 (4) | |
O3 | 0.20672 (10) | 0.47200 (12) | 0.95027 (9) | 0.0585 (4) | |
H1 | 0.1189 (17) | 0.6024 (18) | 0.9211 (12) | 0.070* | |
N1 | 0.14570 (12) | 0.64150 (14) | 0.89310 (10) | 0.0498 (5) | |
H2 | 0.4325 (16) | 0.3581 (17) | 0.9051 (12) | 0.060* | |
N2 | 0.39502 (13) | 0.38567 (13) | 0.93136 (10) | 0.0490 (4) | |
H3 | 0.2403 (16) | 0.4410 (17) | 0.9852 (12) | 0.059* | |
C11 | 0.27118 (14) | 0.52060 (15) | 0.91560 (10) | 0.0423 (5) | |
C12 | 0.23988 (14) | 0.61144 (15) | 0.88334 (10) | 0.0425 (5) | |
C13 | 0.29864 (15) | 0.66334 (16) | 0.84391 (11) | 0.0480 (5) | |
H4 | 0.2773 | 0.7230 | 0.8220 | 0.058* | |
C14 | 0.38962 (15) | 0.62561 (16) | 0.83731 (11) | 0.0499 (5) | |
H5 | 0.4297 | 0.6607 | 0.8114 | 0.060* | |
C15 | 0.42113 (15) | 0.53650 (16) | 0.86887 (11) | 0.0489 (5) | |
H6 | 0.4825 | 0.5123 | 0.8644 | 0.059* | |
C16 | 0.36216 (14) | 0.48271 (15) | 0.90714 (11) | 0.0432 (5) | |
C17 | 0.08927 (15) | 0.71684 (16) | 0.86060 (12) | 0.0494 (5) | |
C18 | −0.01530 (14) | 0.71926 (15) | 0.88138 (10) | 0.0434 (5) | |
C19 | 0.38323 (14) | 0.33635 (16) | 0.99100 (11) | 0.0466 (5) | |
C20 | 0.42135 (14) | 0.22715 (15) | 0.99692 (11) | 0.0458 (5) | |
C21 | −0.07536 (14) | 0.80792 (15) | 0.84594 (11) | 0.0454 (5) | |
C22 | −0.08456 (16) | 0.82160 (17) | 0.77291 (12) | 0.0551 (6) | |
H7 | −0.0488 | 0.7815 | 0.7467 | 0.066* | |
C23 | −0.14565 (17) | 0.89353 (19) | 0.73847 (13) | 0.0642 (7) | |
H8 | −0.1504 | 0.9017 | 0.6896 | 0.077* | |
C24 | −0.19948 (18) | 0.95316 (18) | 0.77652 (14) | 0.0670 (7) | |
H9 | −0.2400 | 1.0023 | 0.7536 | 0.080* | |
C25 | −0.19301 (17) | 0.93967 (17) | 0.84805 (14) | 0.0629 (6) | |
H10 | −0.2302 | 0.9790 | 0.8737 | 0.075* | |
C26 | −0.13133 (16) | 0.86754 (16) | 0.88304 (12) | 0.0533 (5) | |
H11 | −0.1277 | 0.8593 | 0.9318 | 0.064* | |
C31 | −0.07359 (15) | 0.62637 (15) | 0.85137 (11) | 0.0457 (5) | |
C32 | −0.04451 (17) | 0.56479 (17) | 0.80041 (11) | 0.0553 (6) | |
H12 | 0.0151 | 0.5757 | 0.7855 | 0.066* | |
C33 | −0.1034 (2) | 0.48668 (19) | 0.77120 (13) | 0.0673 (7) | |
H13 | −0.0830 | 0.4460 | 0.7369 | 0.081* | |
C34 | −0.1915 (2) | 0.4694 (2) | 0.79290 (15) | 0.0714 (7) | |
H14 | −0.2301 | 0.4163 | 0.7741 | 0.086* | |
C35 | −0.22230 (17) | 0.5309 (2) | 0.84239 (14) | 0.0694 (7) | |
H15 | −0.2824 | 0.5200 | 0.8565 | 0.083* | |
C36 | −0.16451 (16) | 0.60893 (17) | 0.87130 (13) | 0.0570 (6) | |
H16 | −0.1864 | 0.6504 | 0.9045 | 0.068* | |
C41 | 0.00328 (14) | 0.72633 (16) | 0.96277 (11) | 0.0453 (5) | |
C42 | −0.01286 (16) | 0.64870 (17) | 1.00708 (12) | 0.0547 (6) | |
H17 | −0.0422 | 0.5906 | 0.9876 | 0.066* | |
C43 | 0.01380 (18) | 0.6559 (2) | 1.07991 (13) | 0.0714 (7) | |
H18 | 0.0025 | 0.6027 | 1.1087 | 0.086* | |
C44 | 0.05680 (19) | 0.7409 (2) | 1.10988 (14) | 0.0744 (8) | |
H19 | 0.0749 | 0.7456 | 1.1588 | 0.089* | |
C45 | 0.07283 (18) | 0.8190 (2) | 1.06685 (14) | 0.0721 (7) | |
H20 | 0.1014 | 0.8772 | 1.0868 | 0.086* | |
C46 | 0.04686 (16) | 0.81205 (18) | 0.99419 (13) | 0.0595 (6) | |
H21 | 0.0587 | 0.8655 | 0.9657 | 0.071* | |
C51 | 0.50405 (15) | 0.21535 (16) | 0.95227 (11) | 0.0487 (5) | |
C52 | 0.58660 (16) | 0.27575 (18) | 0.96709 (13) | 0.0595 (6) | |
H22 | 0.5908 | 0.3218 | 1.0039 | 0.071* | |
C53 | 0.66201 (18) | 0.2685 (2) | 0.92819 (15) | 0.0727 (7) | |
H23 | 0.7161 | 0.3097 | 0.9388 | 0.087* | |
C54 | 0.6576 (2) | 0.2003 (2) | 0.87355 (16) | 0.0783 (8) | |
H24 | 0.7081 | 0.1956 | 0.8471 | 0.094* | |
C55 | 0.5778 (2) | 0.1397 (2) | 0.85892 (14) | 0.0770 (8) | |
H25 | 0.5748 | 0.0930 | 0.8226 | 0.092* | |
C56 | 0.50086 (18) | 0.14681 (18) | 0.89765 (12) | 0.0618 (6) | |
H26 | 0.4471 | 0.1053 | 0.8867 | 0.074* | |
C61 | 0.45691 (16) | 0.19764 (16) | 1.07547 (12) | 0.0507 (5) | |
C62 | 0.54292 (17) | 0.14379 (17) | 1.09399 (13) | 0.0596 (6) | |
H27 | 0.5815 | 0.1299 | 1.0595 | 0.072* | |
C63 | 0.5720 (2) | 0.11041 (19) | 1.16325 (15) | 0.0723 (8) | |
H28 | 0.6297 | 0.0747 | 1.1746 | 0.087* | |
C64 | 0.5161 (2) | 0.1299 (2) | 1.21459 (15) | 0.0800 (8) | |
H29 | 0.5365 | 0.1092 | 1.2611 | 0.096* | |
C65 | 0.4293 (2) | 0.1805 (2) | 1.19703 (14) | 0.0784 (8) | |
H30 | 0.3905 | 0.1927 | 1.2316 | 0.094* | |
C66 | 0.39968 (18) | 0.21329 (19) | 1.12795 (13) | 0.0628 (6) | |
H31 | 0.3405 | 0.2463 | 1.1166 | 0.075* | |
C71 | 0.33246 (15) | 0.16032 (16) | 0.96796 (11) | 0.0498 (5) | |
C72 | 0.2577 (2) | 0.1927 (2) | 0.91680 (15) | 0.0819 (9) | |
H32 | 0.2579 | 0.2579 | 0.9003 | 0.098* | |
C73 | 0.1821 (2) | 0.1288 (2) | 0.88947 (17) | 0.0973 (11) | |
H33 | 0.1328 | 0.1517 | 0.8545 | 0.117* | |
C74 | 0.1794 (2) | 0.0339 (2) | 0.91322 (14) | 0.0766 (8) | |
H34 | 0.1284 | −0.0080 | 0.8950 | 0.092* | |
C75 | 0.25257 (18) | 0.00040 (19) | 0.96418 (13) | 0.0662 (7) | |
H35 | 0.2515 | −0.0648 | 0.9805 | 0.079* | |
C76 | 0.32788 (17) | 0.06288 (17) | 0.99147 (13) | 0.0590 (6) | |
H36 | 0.3767 | 0.0392 | 1.0264 | 0.071* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0602 (10) | 0.0700 (12) | 0.1047 (14) | 0.0148 (9) | 0.0327 (10) | 0.0456 (11) |
O2 | 0.0734 (10) | 0.0633 (11) | 0.0596 (10) | 0.0226 (9) | 0.0223 (9) | 0.0058 (8) |
O3 | 0.0477 (8) | 0.0555 (10) | 0.0758 (11) | 0.0041 (7) | 0.0204 (8) | 0.0253 (8) |
N1 | 0.0456 (10) | 0.0461 (11) | 0.0606 (11) | 0.0057 (8) | 0.0171 (9) | 0.0155 (9) |
N2 | 0.0508 (10) | 0.0399 (10) | 0.0602 (12) | 0.0063 (8) | 0.0209 (9) | 0.0015 (9) |
C11 | 0.0417 (10) | 0.0385 (12) | 0.0482 (12) | −0.0038 (9) | 0.0112 (9) | 0.0013 (9) |
C12 | 0.0408 (10) | 0.0385 (11) | 0.0486 (12) | −0.0016 (9) | 0.0084 (9) | −0.0008 (9) |
C13 | 0.0484 (12) | 0.0397 (12) | 0.0564 (13) | −0.0038 (10) | 0.0101 (10) | 0.0019 (10) |
C14 | 0.0499 (12) | 0.0450 (13) | 0.0581 (13) | −0.0072 (10) | 0.0188 (11) | 0.0017 (10) |
C15 | 0.0428 (11) | 0.0452 (13) | 0.0613 (13) | 0.0002 (9) | 0.0165 (10) | −0.0029 (10) |
C16 | 0.0444 (11) | 0.0353 (11) | 0.0512 (12) | −0.0002 (9) | 0.0108 (10) | −0.0015 (9) |
C17 | 0.0499 (12) | 0.0417 (12) | 0.0578 (13) | 0.0044 (10) | 0.0123 (11) | 0.0107 (10) |
C18 | 0.0466 (11) | 0.0364 (11) | 0.0477 (12) | 0.0032 (9) | 0.0096 (10) | 0.0066 (9) |
C19 | 0.0426 (11) | 0.0442 (13) | 0.0532 (13) | 0.0025 (9) | 0.0087 (10) | −0.0011 (10) |
C20 | 0.0447 (11) | 0.0392 (12) | 0.0526 (12) | 0.0000 (9) | 0.0043 (10) | 0.0006 (9) |
C21 | 0.0460 (11) | 0.0395 (12) | 0.0514 (13) | 0.0013 (9) | 0.0101 (10) | 0.0063 (9) |
C22 | 0.0563 (13) | 0.0551 (14) | 0.0551 (14) | 0.0096 (11) | 0.0124 (11) | 0.0084 (11) |
C23 | 0.0640 (15) | 0.0680 (17) | 0.0601 (14) | 0.0070 (13) | 0.0078 (12) | 0.0194 (13) |
C24 | 0.0631 (14) | 0.0563 (16) | 0.0810 (18) | 0.0143 (12) | 0.0097 (14) | 0.0224 (13) |
C25 | 0.0657 (15) | 0.0475 (14) | 0.0777 (17) | 0.0134 (12) | 0.0180 (13) | 0.0049 (12) |
C26 | 0.0582 (13) | 0.0459 (13) | 0.0572 (13) | 0.0059 (11) | 0.0137 (11) | 0.0044 (10) |
C31 | 0.0486 (11) | 0.0386 (12) | 0.0496 (12) | 0.0047 (9) | 0.0066 (10) | 0.0046 (9) |
C32 | 0.0594 (13) | 0.0521 (14) | 0.0548 (14) | 0.0072 (11) | 0.0096 (11) | 0.0002 (11) |
C33 | 0.0828 (18) | 0.0569 (16) | 0.0583 (15) | 0.0063 (14) | −0.0009 (14) | −0.0088 (12) |
C34 | 0.0703 (16) | 0.0564 (16) | 0.0798 (18) | −0.0066 (13) | −0.0114 (15) | −0.0075 (14) |
C35 | 0.0540 (14) | 0.0674 (17) | 0.0852 (18) | −0.0099 (13) | 0.0063 (13) | −0.0058 (15) |
C36 | 0.0518 (13) | 0.0515 (14) | 0.0681 (15) | 0.0003 (11) | 0.0104 (12) | −0.0051 (11) |
C41 | 0.0424 (11) | 0.0436 (12) | 0.0508 (12) | 0.0019 (9) | 0.0100 (10) | 0.0044 (10) |
C42 | 0.0567 (13) | 0.0523 (14) | 0.0549 (13) | −0.0027 (11) | 0.0085 (11) | 0.0084 (11) |
C43 | 0.0750 (17) | 0.081 (2) | 0.0582 (15) | −0.0057 (15) | 0.0104 (13) | 0.0187 (14) |
C44 | 0.0721 (17) | 0.099 (2) | 0.0514 (15) | −0.0038 (16) | 0.0071 (13) | −0.0003 (15) |
C45 | 0.0675 (16) | 0.0764 (19) | 0.0696 (17) | −0.0128 (14) | 0.0027 (14) | −0.0137 (15) |
C46 | 0.0617 (14) | 0.0559 (15) | 0.0609 (15) | −0.0088 (11) | 0.0093 (12) | 0.0035 (11) |
C51 | 0.0471 (12) | 0.0425 (12) | 0.0562 (13) | 0.0065 (10) | 0.0072 (10) | 0.0012 (10) |
C52 | 0.0502 (13) | 0.0564 (15) | 0.0725 (16) | 0.0043 (11) | 0.0111 (12) | −0.0028 (12) |
C53 | 0.0526 (14) | 0.0756 (19) | 0.091 (2) | 0.0024 (13) | 0.0156 (14) | 0.0059 (16) |
C54 | 0.0724 (18) | 0.084 (2) | 0.085 (2) | 0.0150 (16) | 0.0334 (16) | 0.0073 (16) |
C55 | 0.091 (2) | 0.0734 (19) | 0.0716 (17) | 0.0092 (16) | 0.0284 (16) | −0.0100 (14) |
C56 | 0.0695 (15) | 0.0539 (15) | 0.0631 (15) | 0.0017 (12) | 0.0143 (13) | −0.0037 (12) |
C61 | 0.0513 (12) | 0.0442 (13) | 0.0546 (13) | −0.0034 (10) | 0.0015 (11) | 0.0022 (10) |
C62 | 0.0600 (14) | 0.0483 (14) | 0.0662 (15) | 0.0001 (11) | −0.0036 (12) | 0.0011 (11) |
C63 | 0.0692 (16) | 0.0599 (17) | 0.0783 (18) | −0.0048 (13) | −0.0172 (15) | 0.0125 (14) |
C64 | 0.090 (2) | 0.076 (2) | 0.0668 (17) | −0.0187 (16) | −0.0100 (17) | 0.0236 (14) |
C65 | 0.084 (2) | 0.088 (2) | 0.0632 (17) | −0.0173 (17) | 0.0117 (15) | 0.0123 (15) |
C66 | 0.0602 (14) | 0.0645 (16) | 0.0633 (16) | −0.0031 (12) | 0.0084 (13) | 0.0089 (12) |
C71 | 0.0482 (12) | 0.0456 (13) | 0.0545 (13) | 0.0003 (10) | 0.0047 (10) | 0.0002 (10) |
C72 | 0.0793 (18) | 0.0566 (17) | 0.096 (2) | −0.0140 (14) | −0.0287 (16) | 0.0199 (15) |
C73 | 0.087 (2) | 0.076 (2) | 0.109 (2) | −0.0224 (16) | −0.0424 (18) | 0.0221 (18) |
C74 | 0.0727 (17) | 0.074 (2) | 0.0778 (18) | −0.0248 (15) | −0.0039 (15) | 0.0012 (15) |
C75 | 0.0714 (15) | 0.0535 (16) | 0.0723 (16) | −0.0142 (13) | 0.0076 (14) | 0.0032 (13) |
C76 | 0.0570 (13) | 0.0502 (14) | 0.0666 (15) | −0.0025 (11) | −0.0001 (12) | 0.0048 (11) |
O1—C17 | 1.206 (2) | C35—H15 | 0.9300 |
O2—C19 | 1.228 (2) | C36—H16 | 0.9300 |
O3—C11 | 1.362 (2) | C41—C42 | 1.382 (3) |
O3—H3 | 0.86 (2) | C41—C46 | 1.392 (3) |
N1—C17 | 1.367 (3) | C42—C43 | 1.383 (3) |
N1—C12 | 1.411 (3) | C42—H17 | 0.9300 |
N1—H1 | 0.87 (2) | C43—C44 | 1.371 (4) |
N2—C19 | 1.349 (3) | C43—H18 | 0.9300 |
N2—C16 | 1.433 (3) | C44—C45 | 1.371 (4) |
N2—H2 | 0.86 (2) | C44—H19 | 0.9300 |
C11—C16 | 1.397 (3) | C45—C46 | 1.379 (3) |
C11—C12 | 1.404 (3) | C45—H20 | 0.9300 |
C12—C13 | 1.383 (3) | C46—H21 | 0.9300 |
C13—C14 | 1.387 (3) | C51—C56 | 1.385 (3) |
C13—H4 | 0.9300 | C51—C52 | 1.398 (3) |
C14—C15 | 1.379 (3) | C52—C53 | 1.380 (3) |
C14—H5 | 0.9300 | C52—H22 | 0.9300 |
C15—C16 | 1.384 (3) | C53—C54 | 1.381 (4) |
C15—H6 | 0.9300 | C53—H23 | 0.9300 |
C17—C18 | 1.567 (3) | C54—C55 | 1.369 (4) |
C18—C41 | 1.536 (3) | C54—H24 | 0.9300 |
C18—C21 | 1.547 (3) | C55—C56 | 1.396 (4) |
C18—C31 | 1.547 (3) | C55—H25 | 0.9300 |
C19—C20 | 1.557 (3) | C56—H26 | 0.9300 |
C20—C51 | 1.544 (3) | C61—C66 | 1.390 (3) |
C20—C61 | 1.553 (3) | C61—C62 | 1.395 (3) |
C20—C71 | 1.557 (3) | C62—C63 | 1.393 (3) |
C21—C26 | 1.386 (3) | C62—H27 | 0.9300 |
C21—C22 | 1.391 (3) | C63—C64 | 1.368 (4) |
C22—C23 | 1.382 (3) | C63—H28 | 0.9300 |
C22—H7 | 0.9300 | C64—C65 | 1.380 (4) |
C23—C24 | 1.378 (3) | C64—H29 | 0.9300 |
C23—H8 | 0.9300 | C65—C66 | 1.389 (3) |
C24—C25 | 1.365 (3) | C65—H30 | 0.9300 |
C24—H9 | 0.9300 | C66—H31 | 0.9300 |
C25—C26 | 1.392 (3) | C71—C72 | 1.379 (3) |
C25—H10 | 0.9300 | C71—C76 | 1.388 (3) |
C26—H11 | 0.9300 | C72—C73 | 1.393 (4) |
C31—C32 | 1.384 (3) | C72—H32 | 0.9300 |
C31—C36 | 1.397 (3) | C73—C74 | 1.355 (4) |
C32—C33 | 1.392 (3) | C73—H33 | 0.9300 |
C32—H12 | 0.9300 | C74—C75 | 1.368 (3) |
C33—C34 | 1.374 (4) | C74—H34 | 0.9300 |
C33—H13 | 0.9300 | C75—C76 | 1.378 (3) |
C34—C35 | 1.372 (4) | C75—H35 | 0.9300 |
C34—H14 | 0.9300 | C76—H36 | 0.9300 |
C35—C36 | 1.381 (3) | ||
C11—O3—H3 | 106.8 (16) | C35—C36—C31 | 120.9 (2) |
C17—N1—C12 | 129.08 (18) | C35—C36—H16 | 119.5 |
C17—N1—H1 | 116.9 (16) | C31—C36—H16 | 119.5 |
C12—N1—H1 | 113.8 (16) | C42—C41—C46 | 117.5 (2) |
C19—N2—C16 | 130.04 (18) | C42—C41—C18 | 123.6 (2) |
C19—N2—H2 | 116.5 (15) | C46—C41—C18 | 118.61 (19) |
C16—N2—H2 | 113.2 (15) | C41—C42—C43 | 121.2 (2) |
O3—C11—C16 | 124.03 (18) | C41—C42—H17 | 119.4 |
O3—C11—C12 | 116.52 (17) | C43—C42—H17 | 119.4 |
C16—C11—C12 | 119.33 (18) | C44—C43—C42 | 120.5 (2) |
C13—C12—C11 | 120.45 (18) | C44—C43—H18 | 119.8 |
C13—C12—N1 | 124.63 (19) | C42—C43—H18 | 119.8 |
C11—C12—N1 | 114.89 (17) | C43—C44—C45 | 119.2 (2) |
C12—C13—C14 | 119.4 (2) | C43—C44—H19 | 120.4 |
C12—C13—H4 | 120.3 | C45—C44—H19 | 120.4 |
C14—C13—H4 | 120.3 | C44—C45—C46 | 120.5 (3) |
C15—C14—C13 | 120.58 (19) | C44—C45—H20 | 119.7 |
C15—C14—H5 | 119.7 | C46—C45—H20 | 119.7 |
C13—C14—H5 | 119.7 | C45—C46—C41 | 121.1 (2) |
C14—C15—C16 | 120.58 (19) | C45—C46—H21 | 119.5 |
C14—C15—H6 | 119.7 | C41—C46—H21 | 119.5 |
C16—C15—H6 | 119.7 | C56—C51—C52 | 117.7 (2) |
C15—C16—C11 | 119.60 (19) | C56—C51—C20 | 123.0 (2) |
C15—C16—N2 | 117.32 (18) | C52—C51—C20 | 119.27 (19) |
C11—C16—N2 | 122.87 (18) | C53—C52—C51 | 121.3 (2) |
O1—C17—N1 | 122.8 (2) | C53—C52—H22 | 119.3 |
O1—C17—C18 | 124.24 (18) | C51—C52—H22 | 119.3 |
N1—C17—C18 | 112.96 (17) | C52—C53—C54 | 120.3 (3) |
C41—C18—C21 | 112.79 (17) | C52—C53—H23 | 119.8 |
C41—C18—C31 | 114.74 (16) | C54—C53—H23 | 119.8 |
C21—C18—C31 | 104.06 (16) | C55—C54—C53 | 119.1 (3) |
C41—C18—C17 | 104.00 (16) | C55—C54—H24 | 120.5 |
C21—C18—C17 | 111.36 (16) | C53—C54—H24 | 120.5 |
C31—C18—C17 | 110.05 (17) | C54—C55—C56 | 121.0 (3) |
O2—C19—N2 | 120.74 (19) | C54—C55—H25 | 119.5 |
O2—C19—C20 | 123.13 (19) | C56—C55—H25 | 119.5 |
N2—C19—C20 | 115.98 (18) | C51—C56—C55 | 120.5 (2) |
C51—C20—C61 | 110.75 (17) | C51—C56—H26 | 119.8 |
C51—C20—C71 | 111.37 (17) | C55—C56—H26 | 119.8 |
C61—C20—C71 | 108.03 (17) | C66—C61—C62 | 117.5 (2) |
C51—C20—C19 | 109.37 (17) | C66—C61—C20 | 121.66 (19) |
C61—C20—C19 | 111.29 (17) | C62—C61—C20 | 120.4 (2) |
C71—C20—C19 | 105.94 (16) | C63—C62—C61 | 121.1 (2) |
C26—C21—C22 | 117.69 (19) | C63—C62—H27 | 119.5 |
C26—C21—C18 | 121.95 (19) | C61—C62—H27 | 119.5 |
C22—C21—C18 | 119.82 (18) | C64—C63—C62 | 120.3 (3) |
C23—C22—C21 | 121.4 (2) | C64—C63—H28 | 119.9 |
C23—C22—H7 | 119.3 | C62—C63—H28 | 119.9 |
C21—C22—H7 | 119.3 | C63—C64—C65 | 119.7 (2) |
C24—C23—C22 | 120.0 (2) | C63—C64—H29 | 120.2 |
C24—C23—H8 | 120.0 | C65—C64—H29 | 120.2 |
C22—C23—H8 | 120.0 | C64—C65—C66 | 120.2 (3) |
C25—C24—C23 | 119.6 (2) | C64—C65—H30 | 119.9 |
C25—C24—H9 | 120.2 | C66—C65—H30 | 119.9 |
C23—C24—H9 | 120.2 | C65—C66—C61 | 121.2 (2) |
C24—C25—C26 | 120.7 (2) | C65—C66—H31 | 119.4 |
C24—C25—H10 | 119.7 | C61—C66—H31 | 119.4 |
C26—C25—H10 | 119.7 | C72—C71—C76 | 117.2 (2) |
C21—C26—C25 | 120.7 (2) | C72—C71—C20 | 122.5 (2) |
C21—C26—H11 | 119.7 | C76—C71—C20 | 120.20 (19) |
C25—C26—H11 | 119.7 | C71—C72—C73 | 120.8 (2) |
C32—C31—C36 | 117.9 (2) | C71—C72—H32 | 119.6 |
C32—C31—C18 | 123.17 (19) | C73—C72—H32 | 119.6 |
C36—C31—C18 | 118.60 (19) | C74—C73—C72 | 120.8 (3) |
C31—C32—C33 | 120.8 (2) | C74—C73—H33 | 119.6 |
C31—C32—H12 | 119.6 | C72—C73—H33 | 119.6 |
C33—C32—H12 | 119.6 | C73—C74—C75 | 119.4 (2) |
C34—C33—C32 | 120.2 (2) | C73—C74—H34 | 120.3 |
C34—C33—H13 | 119.9 | C75—C74—H34 | 120.3 |
C32—C33—H13 | 119.9 | C74—C75—C76 | 120.3 (2) |
C35—C34—C33 | 119.7 (2) | C74—C75—H35 | 119.9 |
C35—C34—H14 | 120.1 | C76—C75—H35 | 119.9 |
C33—C34—H14 | 120.1 | C75—C76—C71 | 121.5 (2) |
C34—C35—C36 | 120.4 (2) | C75—C76—H36 | 119.2 |
C34—C35—H15 | 119.8 | C71—C76—H36 | 119.2 |
C36—C35—H15 | 119.8 | ||
O3—C11—C12—C13 | −176.67 (19) | C34—C35—C36—C31 | −0.5 (4) |
C16—C11—C12—C13 | −0.4 (3) | C32—C31—C36—C35 | 1.7 (3) |
O3—C11—C12—N1 | 1.7 (3) | C18—C31—C36—C35 | 175.6 (2) |
C16—C11—C12—N1 | 177.95 (18) | C21—C18—C41—C42 | 131.0 (2) |
C17—N1—C12—C13 | 8.9 (3) | C31—C18—C41—C42 | 12.1 (3) |
C17—N1—C12—C11 | −169.3 (2) | C17—C18—C41—C42 | −108.2 (2) |
C11—C12—C13—C14 | −1.0 (3) | C21—C18—C41—C46 | −54.9 (2) |
N1—C12—C13—C14 | −179.12 (19) | C31—C18—C41—C46 | −173.88 (18) |
C12—C13—C14—C15 | 0.9 (3) | C17—C18—C41—C46 | 65.9 (2) |
C13—C14—C15—C16 | 0.6 (3) | C46—C41—C42—C43 | −0.3 (3) |
C14—C15—C16—C11 | −1.9 (3) | C18—C41—C42—C43 | 173.8 (2) |
C14—C15—C16—N2 | 172.96 (19) | C41—C42—C43—C44 | 0.2 (4) |
O3—C11—C16—C15 | 177.8 (2) | C42—C43—C44—C45 | 0.2 (4) |
C12—C11—C16—C15 | 1.8 (3) | C43—C44—C45—C46 | −0.6 (4) |
O3—C11—C16—N2 | 3.2 (3) | C44—C45—C46—C41 | 0.5 (4) |
C12—C11—C16—N2 | −172.78 (19) | C42—C41—C46—C45 | 0.0 (3) |
C19—N2—C16—C15 | 146.4 (2) | C18—C41—C46—C45 | −174.4 (2) |
C19—N2—C16—C11 | −38.8 (3) | C61—C20—C51—C56 | 114.9 (2) |
C12—N1—C17—O1 | −6.0 (4) | C71—C20—C51—C56 | −5.3 (3) |
C12—N1—C17—C18 | 174.58 (19) | C19—C20—C51—C56 | −122.1 (2) |
O1—C17—C18—C41 | −123.4 (2) | C61—C20—C51—C52 | −64.8 (2) |
N1—C17—C18—C41 | 56.0 (2) | C71—C20—C51—C52 | 174.91 (19) |
O1—C17—C18—C21 | −1.7 (3) | C19—C20—C51—C52 | 58.2 (2) |
N1—C17—C18—C21 | 177.72 (18) | C56—C51—C52—C53 | 0.8 (3) |
O1—C17—C18—C31 | 113.2 (2) | C20—C51—C52—C53 | −179.4 (2) |
N1—C17—C18—C31 | −67.4 (2) | C51—C52—C53—C54 | −0.4 (4) |
C16—N2—C19—O2 | −0.9 (3) | C52—C53—C54—C55 | −0.5 (4) |
C16—N2—C19—C20 | 174.75 (18) | C53—C54—C55—C56 | 0.9 (4) |
O2—C19—C20—C51 | −158.2 (2) | C52—C51—C56—C55 | −0.4 (3) |
N2—C19—C20—C51 | 26.2 (2) | C20—C51—C56—C55 | 179.8 (2) |
O2—C19—C20—C61 | −35.6 (3) | C54—C55—C56—C51 | −0.4 (4) |
N2—C19—C20—C61 | 148.92 (18) | C51—C20—C61—C66 | 172.1 (2) |
O2—C19—C20—C71 | 81.6 (2) | C71—C20—C61—C66 | −65.7 (3) |
N2—C19—C20—C71 | −93.9 (2) | C19—C20—C61—C66 | 50.2 (3) |
C41—C18—C21—C26 | −19.3 (3) | C51—C20—C61—C62 | −15.5 (3) |
C31—C18—C21—C26 | 105.6 (2) | C71—C20—C61—C62 | 106.7 (2) |
C17—C18—C21—C26 | −135.8 (2) | C19—C20—C61—C62 | −137.4 (2) |
C41—C18—C21—C22 | 169.23 (19) | C66—C61—C62—C63 | −2.4 (3) |
C31—C18—C21—C22 | −65.8 (2) | C20—C61—C62—C63 | −175.2 (2) |
C17—C18—C21—C22 | 52.7 (3) | C61—C62—C63—C64 | 0.1 (4) |
C26—C21—C22—C23 | 1.4 (3) | C62—C63—C64—C65 | 1.8 (4) |
C18—C21—C22—C23 | 173.2 (2) | C63—C64—C65—C66 | −1.3 (4) |
C21—C22—C23—C24 | −0.4 (4) | C64—C65—C66—C61 | −1.1 (4) |
C22—C23—C24—C25 | −0.9 (4) | C62—C61—C66—C65 | 2.9 (4) |
C23—C24—C25—C26 | 1.1 (4) | C20—C61—C66—C65 | 175.6 (2) |
C22—C21—C26—C25 | −1.2 (3) | C51—C20—C71—C72 | −89.3 (3) |
C18—C21—C26—C25 | −172.8 (2) | C61—C20—C71—C72 | 148.9 (2) |
C24—C25—C26—C21 | −0.1 (4) | C19—C20—C71—C72 | 29.5 (3) |
C41—C18—C31—C32 | −130.8 (2) | C51—C20—C71—C76 | 88.2 (2) |
C21—C18—C31—C32 | 105.5 (2) | C61—C20—C71—C76 | −33.7 (3) |
C17—C18—C31—C32 | −13.9 (3) | C19—C20—C71—C76 | −153.0 (2) |
C41—C18—C31—C36 | 55.7 (2) | C76—C71—C72—C73 | −1.0 (4) |
C21—C18—C31—C36 | −68.1 (2) | C20—C71—C72—C73 | 176.5 (3) |
C17—C18—C31—C36 | 172.52 (18) | C71—C72—C73—C74 | 0.9 (5) |
C36—C31—C32—C33 | −1.3 (3) | C72—C73—C74—C75 | −0.6 (5) |
C18—C31—C32—C33 | −175.0 (2) | C73—C74—C75—C76 | 0.5 (4) |
C31—C32—C33—C34 | −0.2 (3) | C74—C75—C76—C71 | −0.6 (4) |
C32—C33—C34—C35 | 1.5 (4) | C72—C71—C76—C75 | 0.9 (4) |
C33—C34—C35—C36 | −1.1 (4) | C20—C71—C76—C75 | −176.7 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O3 | 0.87 (2) | 2.16 (2) | 2.607 (2) | 112 (2) |
O3—H3···O2 | 0.86 (2) | 1.78 (2) | 2.604 (2) | 159 (2) |