Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806042851/ob2085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806042851/ob2085Isup2.hkl |
CCDC reference: 628037
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
C25H29NO3 | Dx = 1.149 Mg m−3 |
Mr = 391.49 | Melting point: 384 K |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 5993 reflections |
a = 10.2911 (2) Å | θ = 2.0–28.2° |
b = 14.0805 (3) Å | µ = 0.08 mm−1 |
c = 15.6118 (3) Å | T = 273 K |
V = 2262.21 (8) Å3 | Block, colorless |
Z = 4 | 0.31 × 0.25 × 0.19 mm |
F(000) = 840 |
Bruker SMART APEX-2 CCD area-detector diffractometer | 3070 independent reflections |
Radiation source: fine-focus sealed tube | 2359 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
φ and ω scans | θmax = 28.2°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −13→13 |
Tmin = 0.971, Tmax = 0.979 | k = −18→18 |
20251 measured reflections | l = −20→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.041 | H-atom parameters constrained |
wR(F2) = 0.121 | w = 1/[σ2(Fo2) + (0.0654P)2 + 0.1915P] where P = (Fo2 + 2Fc2)/3 |
S = 1.01 | (Δ/σ)max = 0.001 |
3070 reflections | Δρmax = 0.20 e Å−3 |
275 parameters | Δρmin = −0.19 e Å−3 |
17 restraints | Extinction correction: SHELXL97 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.043 (6) |
Experimental. Spectroscopic analysis: 1H NMR (CDCl3, δ, p.p.m.): 7.37–6.00 (8H, m, Ar), 5.01 (s, 1H, PhCH–), 3.49–3.44 (q, 1H), 3.23–3.13 (m, 2H), 1.61 (s, 3H), 1.67–1.64 (m, 2H), 0.97 (s, 3H), 0.82–0.79 (t, 3H); 13C NMR (CDCl3, δ, p.p.m.): 172.4, 158.0, 154.1, 141.85–106.20 (Ar), 83.3, 68.0, 40.4, 37.4, 29.8, 28.1, 24.5, 12.4; ESI-MS for C25H29O3N, Calcd. 414(M+Na+); Found: 414(M+Na+). |
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 | 0.44076 (19) | 0.93655 (14) | 0.04012 (15) | 0.0901 (6) | |
O2 | 0.37297 (16) | 0.79593 (12) | −0.00837 (12) | 0.0718 (5) | |
O3 | 0.06448 (18) | 0.92985 (11) | 0.14736 (11) | 0.0714 (5) | |
N1 | 0.23632 (17) | 0.87519 (12) | 0.07545 (12) | 0.0546 (4) | |
C1 | 0.3578 (2) | 0.87749 (18) | 0.03624 (17) | 0.0657 (6) | |
C2 | 0.2493 (2) | 0.74262 (18) | −0.01161 (15) | 0.0623 (6) | |
C3 | 0.1803 (2) | 0.77892 (14) | 0.06982 (13) | 0.0519 (5) | |
H3A | 0.0867 | 0.7837 | 0.0588 | 0.062* | |
C4 | 0.2836 (3) | 0.63844 (19) | −0.01243 (19) | 0.0784 (7) | |
H4A | 0.3256 | 0.6230 | −0.0656 | 0.118* | |
H4B | 0.2059 | 0.6013 | −0.0066 | 0.118* | |
H4C | 0.3413 | 0.6247 | 0.0343 | 0.118* | |
C5 | 0.1764 (3) | 0.7738 (3) | −0.09173 (17) | 0.0897 (9) | |
H5A | 0.2210 | 0.7507 | −0.1416 | 0.135* | |
H5B | 0.1725 | 0.8418 | −0.0936 | 0.135* | |
H5C | 0.0899 | 0.7484 | −0.0905 | 0.135* | |
C6 | 0.2025 (2) | 0.72197 (15) | 0.15048 (13) | 0.0555 (5) | |
C7 | 0.1146 (3) | 0.65228 (16) | 0.17310 (17) | 0.0698 (7) | |
H7A | 0.0411 | 0.6422 | 0.1396 | 0.084* | |
C8 | 0.1352 (4) | 0.59704 (19) | 0.2456 (2) | 0.0893 (10) | |
H8A | 0.0756 | 0.5500 | 0.2600 | 0.107* | |
C9 | 0.2415 (5) | 0.6110 (2) | 0.29565 (19) | 0.1001 (11) | |
H9A | 0.2543 | 0.5739 | 0.3442 | 0.120* | |
C10 | 0.3300 (4) | 0.6801 (3) | 0.27416 (18) | 0.0986 (10) | |
H10A | 0.4029 | 0.6895 | 0.3083 | 0.118* | |
C11 | 0.3112 (3) | 0.7359 (2) | 0.20190 (16) | 0.0756 (7) | |
H11A | 0.3714 | 0.7826 | 0.1879 | 0.091* | |
C12 | 0.1689 (2) | 0.94840 (15) | 0.11507 (13) | 0.0542 (5) | |
C13 | 0.2230 (3) | 1.04713 (15) | 0.11489 (14) | 0.0613 (6) | |
H13A | 0.3062 | 1.0474 | 0.0857 | 0.074* | |
H13B | 0.2369 | 1.0679 | 0.1734 | 0.074* | |
C14 | 0.1294 (2) | 1.11633 (14) | 0.06963 (13) | 0.0530 (5) | |
H14A | 0.0448 | 1.1112 | 0.0981 | 0.064* | |
C15 | 0.1107 (2) | 1.08751 (15) | −0.02319 (13) | 0.0532 (5) | |
C16 | −0.0090 (3) | 1.0616 (2) | −0.05399 (16) | 0.0715 (7) | |
H16A | −0.0805 | 1.0625 | −0.0176 | 0.086* | |
C17 | −0.0251 (3) | 1.0341 (3) | −0.13893 (19) | 0.0907 (9) | |
H17A | −0.1069 | 1.0166 | −0.1587 | 0.109* | |
C18 | 0.0779 (4) | 1.0325 (2) | −0.19304 (17) | 0.0877 (9) | |
H18A | 0.0669 | 1.0141 | −0.2498 | 0.105* | |
C19 | 0.1976 (3) | 1.0580 (2) | −0.16365 (16) | 0.0868 (9) | |
H19A | 0.2683 | 1.0575 | −0.2007 | 0.104* | |
C20 | 0.2145 (3) | 1.0845 (2) | −0.07952 (16) | 0.0739 (7) | |
H20A | 0.2971 | 1.1007 | −0.0602 | 0.089* | |
C21 | 0.1760 (3) | 1.21898 (14) | 0.07973 (14) | 0.0623 (6) | 0.196 (11) |
H21B | 0.2703 | 1.2188 | 0.0713 | 0.075* | 0.196 (11) |
C22 | 0.151 (3) | 1.2576 (15) | 0.1696 (6) | 0.0766 (13) | 0.196 (11) |
H22A | 0.2300 | 1.2823 | 0.1946 | 0.092* | 0.196 (11) |
H22B | 0.1166 | 1.2082 | 0.2066 | 0.092* | 0.196 (11) |
C23 | 0.051 (3) | 1.3370 (13) | 0.1578 (13) | 0.110 (2) | 0.196 (11) |
H23A | −0.0371 | 1.3123 | 0.1627 | 0.132* | 0.196 (11) |
H23B | 0.0627 | 1.3864 | 0.2004 | 0.132* | 0.196 (11) |
C24 | 0.075 (3) | 1.3752 (10) | 0.0682 (13) | 0.1048 (17) | 0.196 (11) |
H24A | −0.0035 | 1.4017 | 0.0439 | 0.126* | 0.196 (11) |
H24B | 0.1419 | 1.4240 | 0.0691 | 0.126* | 0.196 (11) |
C25 | 0.120 (3) | 1.2897 (12) | 0.0173 (8) | 0.0820 (13) | 0.196 (11) |
H25A | 0.0475 | 1.2619 | −0.0133 | 0.098* | 0.196 (11) |
H25B | 0.1856 | 1.3084 | −0.0241 | 0.098* | 0.196 (11) |
C21' | 0.1760 (3) | 1.21898 (14) | 0.07973 (14) | 0.0623 (6) | 0.804 (11) |
H21A | 0.2594 | 1.2263 | 0.0501 | 0.075* | 0.804 (11) |
C22' | 0.1923 (6) | 1.2500 (4) | 0.1744 (2) | 0.0766 (13) | 0.804 (11) |
H22C | 0.1481 | 1.2059 | 0.2122 | 0.092* | 0.804 (11) |
H22D | 0.2836 | 1.2518 | 0.1898 | 0.092* | 0.804 (11) |
C23' | 0.1331 (9) | 1.3477 (3) | 0.1814 (3) | 0.110 (2) | 0.804 (11) |
H23C | 0.0542 | 1.3452 | 0.2154 | 0.132* | 0.804 (11) |
H23D | 0.1935 | 1.3908 | 0.2090 | 0.132* | 0.804 (11) |
C24' | 0.1033 (6) | 1.3812 (3) | 0.0940 (4) | 0.1048 (17) | 0.804 (11) |
H24C | 0.1763 | 1.4160 | 0.0704 | 0.126* | 0.804 (11) |
H24D | 0.0277 | 1.4224 | 0.0944 | 0.126* | 0.804 (11) |
C25' | 0.0769 (5) | 1.2923 (3) | 0.0422 (4) | 0.0820 (13) | 0.804 (11) |
H25C | 0.0925 | 1.3032 | −0.0183 | 0.098* | 0.804 (11) |
H25D | −0.0119 | 1.2708 | 0.0500 | 0.098* | 0.804 (11) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0665 (10) | 0.0701 (11) | 0.1337 (18) | −0.0101 (10) | 0.0223 (11) | 0.0069 (11) |
O2 | 0.0618 (9) | 0.0691 (10) | 0.0847 (11) | 0.0037 (8) | 0.0266 (9) | −0.0014 (9) |
O3 | 0.0817 (11) | 0.0600 (9) | 0.0726 (10) | 0.0062 (9) | 0.0290 (9) | 0.0003 (8) |
N1 | 0.0552 (9) | 0.0472 (9) | 0.0615 (10) | 0.0012 (8) | 0.0116 (8) | 0.0059 (8) |
C1 | 0.0586 (13) | 0.0582 (13) | 0.0804 (16) | 0.0052 (11) | 0.0156 (12) | 0.0120 (12) |
C2 | 0.0652 (13) | 0.0654 (13) | 0.0562 (11) | 0.0001 (11) | 0.0122 (11) | −0.0026 (10) |
C3 | 0.0543 (11) | 0.0470 (10) | 0.0545 (11) | −0.0001 (9) | 0.0101 (9) | −0.0002 (9) |
C4 | 0.0903 (18) | 0.0676 (15) | 0.0773 (15) | 0.0069 (14) | 0.0212 (15) | −0.0144 (13) |
C5 | 0.099 (2) | 0.114 (2) | 0.0559 (13) | 0.009 (2) | 0.0052 (14) | 0.0030 (15) |
C6 | 0.0707 (13) | 0.0446 (10) | 0.0513 (10) | 0.0032 (10) | 0.0128 (10) | −0.0024 (9) |
C7 | 0.0856 (17) | 0.0540 (12) | 0.0698 (14) | −0.0047 (12) | 0.0226 (13) | −0.0023 (11) |
C8 | 0.133 (3) | 0.0532 (14) | 0.0812 (19) | −0.0048 (16) | 0.045 (2) | 0.0041 (13) |
C9 | 0.167 (4) | 0.0748 (19) | 0.0586 (15) | 0.018 (2) | 0.021 (2) | 0.0149 (14) |
C10 | 0.136 (3) | 0.100 (2) | 0.0598 (14) | 0.011 (2) | −0.0135 (18) | 0.0079 (16) |
C11 | 0.0961 (19) | 0.0694 (15) | 0.0613 (13) | −0.0067 (15) | −0.0014 (13) | 0.0041 (12) |
C12 | 0.0663 (13) | 0.0497 (11) | 0.0467 (10) | 0.0061 (10) | 0.0010 (10) | 0.0049 (9) |
C13 | 0.0756 (14) | 0.0515 (12) | 0.0567 (11) | 0.0011 (11) | −0.0071 (11) | 0.0024 (10) |
C14 | 0.0629 (12) | 0.0485 (10) | 0.0477 (10) | 0.0047 (10) | 0.0050 (10) | 0.0026 (9) |
C15 | 0.0649 (12) | 0.0485 (11) | 0.0462 (10) | 0.0007 (9) | 0.0011 (9) | 0.0041 (9) |
C16 | 0.0653 (14) | 0.0866 (18) | 0.0627 (13) | −0.0051 (13) | −0.0003 (12) | −0.0058 (13) |
C17 | 0.0868 (18) | 0.112 (2) | 0.0735 (17) | −0.0086 (18) | −0.0163 (16) | −0.0139 (17) |
C18 | 0.121 (2) | 0.094 (2) | 0.0478 (12) | 0.0019 (19) | −0.0050 (16) | −0.0064 (13) |
C19 | 0.103 (2) | 0.103 (2) | 0.0546 (13) | −0.0093 (19) | 0.0192 (15) | −0.0070 (14) |
C20 | 0.0745 (15) | 0.0870 (18) | 0.0600 (13) | −0.0106 (14) | 0.0095 (13) | −0.0055 (13) |
C21 | 0.0833 (16) | 0.0481 (11) | 0.0556 (11) | 0.0031 (11) | 0.0008 (12) | 0.0007 (10) |
C22 | 0.101 (4) | 0.0645 (17) | 0.0642 (15) | 0.002 (2) | −0.0116 (18) | −0.0112 (13) |
C23 | 0.164 (6) | 0.071 (2) | 0.095 (3) | 0.009 (3) | 0.022 (4) | −0.023 (2) |
C24 | 0.109 (4) | 0.0638 (18) | 0.142 (5) | 0.014 (2) | −0.031 (3) | −0.015 (2) |
C25 | 0.103 (3) | 0.0579 (16) | 0.085 (3) | 0.019 (2) | −0.008 (2) | 0.0039 (18) |
C21' | 0.0833 (16) | 0.0481 (11) | 0.0556 (11) | 0.0031 (11) | 0.0008 (12) | 0.0007 (10) |
C22' | 0.101 (4) | 0.0645 (17) | 0.0642 (15) | 0.002 (2) | −0.0116 (18) | −0.0112 (13) |
C23' | 0.164 (6) | 0.071 (2) | 0.095 (3) | 0.009 (3) | 0.022 (4) | −0.023 (2) |
C24' | 0.109 (4) | 0.0638 (18) | 0.142 (5) | 0.014 (2) | −0.031 (3) | −0.015 (2) |
C25' | 0.103 (3) | 0.0579 (16) | 0.085 (3) | 0.019 (2) | −0.008 (2) | 0.0039 (18) |
O1—C1 | 1.193 (3) | C15—C16 | 1.372 (3) |
O2—C1 | 1.352 (3) | C15—C20 | 1.384 (3) |
O2—C2 | 1.478 (3) | C16—C17 | 1.392 (4) |
O3—C12 | 1.215 (3) | C16—H16A | 0.9300 |
N1—C12 | 1.388 (3) | C17—C18 | 1.355 (4) |
N1—C1 | 1.393 (3) | C17—H17A | 0.9300 |
N1—C3 | 1.476 (3) | C18—C19 | 1.362 (5) |
C2—C4 | 1.509 (4) | C18—H18A | 0.9300 |
C2—C5 | 1.523 (4) | C19—C20 | 1.377 (4) |
C2—C3 | 1.544 (3) | C19—H19A | 0.9300 |
C3—C6 | 1.510 (3) | C20—H20A | 0.9300 |
C3—H3A | 0.9800 | C21—C25 | 1.507 (8) |
C4—H4A | 0.9600 | C21—C22 | 1.527 (9) |
C4—H4B | 0.9600 | C21—H21B | 0.9800 |
C4—H4C | 0.9600 | C22—C23 | 1.531 (9) |
C5—H5A | 0.9600 | C22—H22A | 0.9700 |
C5—H5B | 0.9600 | C22—H22B | 0.9700 |
C5—H5C | 0.9600 | C23—C24 | 1.521 (10) |
C6—C7 | 1.380 (3) | C23—H23A | 0.9700 |
C6—C11 | 1.391 (4) | C23—H23B | 0.9700 |
C7—C8 | 1.390 (4) | C24—C25 | 1.514 (9) |
C7—H7A | 0.9300 | C24—H24A | 0.9700 |
C8—C9 | 1.358 (5) | C24—H24B | 0.9700 |
C8—H8A | 0.9300 | C25—H25A | 0.9700 |
C9—C10 | 1.375 (5) | C25—H25B | 0.9700 |
C9—H9A | 0.9300 | C22'—C23' | 1.509 (6) |
C10—C11 | 1.388 (4) | C22'—H22C | 0.9700 |
C10—H10A | 0.9300 | C22'—H22D | 0.9700 |
C11—H11A | 0.9300 | C23'—C24' | 1.475 (7) |
C12—C13 | 1.497 (3) | C23'—H23C | 0.9700 |
C13—C14 | 1.541 (3) | C23'—H23D | 0.9700 |
C13—H13A | 0.9700 | C24'—C25' | 1.515 (6) |
C13—H13B | 0.9700 | C24'—H24C | 0.9700 |
C14—C15 | 1.517 (3) | C24'—H24D | 0.9700 |
C14—C21 | 1.531 (3) | C25'—H25C | 0.9700 |
C14—H14A | 0.9800 | C25'—H25D | 0.9700 |
C1—O2—C2 | 110.48 (17) | C16—C15—C14 | 121.3 (2) |
C12—N1—C1 | 128.9 (2) | C20—C15—C14 | 121.1 (2) |
C12—N1—C3 | 120.87 (17) | C15—C16—C17 | 121.0 (3) |
C1—N1—C3 | 110.26 (18) | C15—C16—H16A | 119.5 |
O1—C1—O2 | 122.4 (2) | C17—C16—H16A | 119.5 |
O1—C1—N1 | 129.5 (2) | C18—C17—C16 | 120.4 (3) |
O2—C1—N1 | 108.1 (2) | C18—C17—H17A | 119.8 |
O2—C2—C4 | 107.0 (2) | C16—C17—H17A | 119.8 |
O2—C2—C5 | 107.8 (2) | C17—C18—C19 | 119.5 (2) |
C4—C2—C5 | 112.8 (2) | C17—C18—H18A | 120.2 |
O2—C2—C3 | 101.54 (17) | C19—C18—H18A | 120.2 |
C4—C2—C3 | 115.9 (2) | C18—C19—C20 | 120.5 (3) |
C5—C2—C3 | 110.7 (2) | C18—C19—H19A | 119.8 |
N1—C3—C6 | 112.27 (18) | C20—C19—H19A | 119.8 |
N1—C3—C2 | 99.97 (17) | C19—C20—C15 | 121.1 (3) |
C6—C3—C2 | 116.19 (17) | C19—C20—H20A | 119.4 |
N1—C3—H3A | 109.3 | C15—C20—H20A | 119.4 |
C6—C3—H3A | 109.3 | C25—C21—C22 | 107.0 (5) |
C2—C3—H3A | 109.3 | C25—C21—C14 | 116.0 (9) |
C2—C4—H4A | 109.5 | C22—C21—C14 | 112.2 (11) |
C2—C4—H4B | 109.5 | C25—C21—H21B | 107.1 |
H4A—C4—H4B | 109.5 | C22—C21—H21B | 107.1 |
C2—C4—H4C | 109.5 | C14—C21—H21B | 107.1 |
H4A—C4—H4C | 109.5 | C21—C22—C23 | 105.4 (6) |
H4B—C4—H4C | 109.5 | C21—C22—H22A | 110.7 |
C2—C5—H5A | 109.5 | C23—C22—H22A | 110.7 |
C2—C5—H5B | 109.5 | C21—C22—H22B | 110.7 |
H5A—C5—H5B | 109.5 | C23—C22—H22B | 110.7 |
C2—C5—H5C | 109.5 | H22A—C22—H22B | 108.8 |
H5A—C5—H5C | 109.5 | C24—C23—C22 | 104.8 (7) |
H5B—C5—H5C | 109.5 | C24—C23—H23A | 110.8 |
C7—C6—C11 | 118.7 (2) | C22—C23—H23A | 110.8 |
C7—C6—C3 | 119.4 (2) | C24—C23—H23B | 110.8 |
C11—C6—C3 | 121.9 (2) | C22—C23—H23B | 110.8 |
C6—C7—C8 | 120.4 (3) | H23A—C23—H23B | 108.9 |
C6—C7—H7A | 119.8 | C25—C24—C23 | 104.6 (7) |
C8—C7—H7A | 119.8 | C25—C24—H24A | 110.8 |
C9—C8—C7 | 120.7 (3) | C23—C24—H24A | 110.8 |
C9—C8—H8A | 119.6 | C25—C24—H24B | 110.8 |
C7—C8—H8A | 119.6 | C23—C24—H24B | 110.8 |
C8—C9—C10 | 119.7 (3) | H24A—C24—H24B | 108.9 |
C8—C9—H9A | 120.2 | C21—C25—C24 | 107.6 (6) |
C10—C9—H9A | 120.2 | C21—C25—H25A | 110.2 |
C9—C10—C11 | 120.5 (3) | C24—C25—H25A | 110.2 |
C9—C10—H10A | 119.8 | C21—C25—H25B | 110.2 |
C11—C10—H10A | 119.8 | C24—C25—H25B | 110.2 |
C10—C11—C6 | 120.1 (3) | H25A—C25—H25B | 108.5 |
C10—C11—H11A | 120.0 | C23'—C22'—H22C | 110.5 |
C6—C11—H11A | 120.0 | C23'—C22'—H22D | 110.5 |
O3—C12—N1 | 117.9 (2) | H22C—C22'—H22D | 108.6 |
O3—C12—C13 | 121.9 (2) | C24'—C23'—C22' | 108.0 (3) |
N1—C12—C13 | 120.2 (2) | C24'—C23'—H23C | 110.1 |
C12—C13—C14 | 110.8 (2) | C22'—C23'—H23C | 110.1 |
C12—C13—H13A | 109.5 | C24'—C23'—H23D | 110.1 |
C14—C13—H13A | 109.5 | C22'—C23'—H23D | 110.1 |
C12—C13—H13B | 109.5 | H23C—C23'—H23D | 108.4 |
C14—C13—H13B | 109.5 | C23'—C24'—C25' | 105.5 (3) |
H13A—C13—H13B | 108.1 | C23'—C24'—H24C | 110.6 |
C15—C14—C21 | 112.99 (17) | C25'—C24'—H24C | 110.6 |
C15—C14—C13 | 110.38 (18) | C23'—C24'—H24D | 110.6 |
C21—C14—C13 | 110.76 (19) | C25'—C24'—H24D | 110.6 |
C15—C14—H14A | 107.5 | H24C—C24'—H24D | 108.8 |
C21—C14—H14A | 107.5 | C24'—C25'—H25C | 111.1 |
C13—C14—H14A | 107.5 | C24'—C25'—H25D | 111.1 |
C16—C15—C20 | 117.5 (2) | H25C—C25'—H25D | 109.1 |
C2—O2—C1—O1 | −172.3 (2) | C3—N1—C12—O3 | 2.4 (3) |
C2—O2—C1—N1 | 9.6 (3) | C1—N1—C12—C13 | 3.7 (3) |
C12—N1—C1—O1 | 14.4 (4) | C3—N1—C12—C13 | −175.75 (19) |
C3—N1—C1—O1 | −166.1 (3) | O3—C12—C13—C14 | −58.5 (3) |
C12—N1—C1—O2 | −167.7 (2) | N1—C12—C13—C14 | 119.6 (2) |
C3—N1—C1—O2 | 11.8 (3) | C12—C13—C14—C15 | −61.5 (2) |
C1—O2—C2—C4 | −147.4 (2) | C12—C13—C14—C21 | 172.56 (18) |
C1—O2—C2—C5 | 90.9 (2) | C21—C14—C15—C16 | −117.6 (3) |
C1—O2—C2—C3 | −25.5 (2) | C13—C14—C15—C16 | 117.7 (3) |
C12—N1—C3—C6 | −83.1 (2) | C21—C14—C15—C20 | 63.7 (3) |
C1—N1—C3—C6 | 97.4 (2) | C13—C14—C15—C20 | −60.9 (3) |
C12—N1—C3—C2 | 153.16 (19) | C20—C15—C16—C17 | −0.4 (4) |
C1—N1—C3—C2 | −26.4 (2) | C14—C15—C16—C17 | −179.1 (3) |
O2—C2—C3—N1 | 29.5 (2) | C15—C16—C17—C18 | −0.1 (5) |
C4—C2—C3—N1 | 145.1 (2) | C16—C17—C18—C19 | 0.1 (5) |
C5—C2—C3—N1 | −84.7 (2) | C17—C18—C19—C20 | 0.5 (5) |
O2—C2—C3—C6 | −91.5 (2) | C18—C19—C20—C15 | −1.1 (5) |
C4—C2—C3—C6 | 24.1 (3) | C16—C15—C20—C19 | 1.0 (4) |
C5—C2—C3—C6 | 154.2 (2) | C14—C15—C20—C19 | 179.7 (3) |
N1—C3—C6—C7 | 151.4 (2) | C15—C14—C21—C25 | 37.1 (10) |
C2—C3—C6—C7 | −94.4 (2) | C13—C14—C21—C25 | 161.5 (9) |
N1—C3—C6—C11 | −30.3 (3) | C15—C14—C21—C22 | 160.5 (9) |
C2—C3—C6—C11 | 83.9 (3) | C13—C14—C21—C22 | −75.1 (10) |
C11—C6—C7—C8 | −0.3 (3) | C25—C21—C22—C23 | 14 (2) |
C3—C6—C7—C8 | 178.0 (2) | C14—C21—C22—C23 | −114.2 (16) |
C6—C7—C8—C9 | 0.4 (4) | C21—C22—C23—C24 | −29 (2) |
C7—C8—C9—C10 | −0.3 (5) | C22—C23—C24—C25 | 33 (2) |
C8—C9—C10—C11 | 0.2 (5) | C22—C21—C25—C24 | 6 (2) |
C9—C10—C11—C6 | −0.2 (5) | C14—C21—C25—C24 | 132.3 (17) |
C7—C6—C11—C10 | 0.2 (4) | C23—C24—C25—C21 | −24 (2) |
C3—C6—C11—C10 | −178.1 (2) | C22'—C23'—C24'—C25' | 29.0 (6) |
C1—N1—C12—O3 | −178.1 (2) |