Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806022513/lh2097sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806022513/lh2097Isup2.hkl |
CCDC reference: 613775
Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); 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, 1997); software used to prepare material for publication: SHELXTL.
C27H50N2O4 | F(000) = 1032 |
Mr = 466.69 | Dx = 1.084 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2068 reflections |
a = 11.871 (3) Å | θ = 2.5–20.1° |
b = 18.170 (4) Å | µ = 0.07 mm−1 |
c = 13.260 (3) Å | T = 294 K |
β = 91.386 (4)° | Block, colourless |
V = 2859.4 (11) Å3 | 0.22 × 0.20 × 0.10 mm |
Z = 4 |
Bruker SMART-CCD area-detector diffractometer | 5037 independent reflections |
Radiation source: fine-focus sealed tube | 2237 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.066 |
φ and ω scans | θmax = 25.0°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −14→14 |
Tmin = 0.984, Tmax = 0.993 | k = −20→21 |
14581 measured reflections | l = −15→11 |
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)] = 0.054 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.165 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0647P)2 + 0.2574P] where P = (Fo2 + 2Fc2)/3 |
5037 reflections | (Δ/σ)max = 0.002 |
309 parameters | Δρmax = 0.17 e Å−3 |
6 restraints | Δρmin = −0.18 e Å−3 |
Experimental. 1H NMR (CDCl3): δ 0.90 (t, 3H), 1.07 (s, 12H), 1.16 (s, 12H), 1.32 (m, 4H), 1.47 (m, 4H), 2.17 (s, 6H), 3.26 (t, 1H), 5.06 (m, 2H) 13C NMR (CDCl3): δ 14.04, 20.87, 22.58, 28.23, 28.58, 29.69, 33.38, 45.84, 45.91, 52.58, 55.41, 69.05, 169.50 |
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 | 0.04402 (16) | 0.01242 (10) | 0.24909 (14) | 0.0546 (6) | |
O2 | −0.06481 (19) | −0.01622 (14) | 0.37872 (18) | 0.0859 (8) | |
O3 | −0.00900 (15) | 0.16230 (10) | 0.17701 (13) | 0.0481 (5) | |
O4 | −0.12095 (16) | 0.08696 (12) | 0.08518 (16) | 0.0666 (7) | |
N1 | 0.3419 (2) | −0.11008 (15) | 0.2838 (2) | 0.0665 (8) | |
N2 | 0.25314 (19) | 0.22335 (13) | −0.01251 (18) | 0.0536 (7) | |
C1 | 0.1203 (2) | −0.04904 (16) | 0.2721 (2) | 0.0512 (8) | |
H1 | 0.0769 | −0.0934 | 0.2871 | 0.061* | |
C2 | 0.1994 (2) | −0.03125 (18) | 0.3587 (2) | 0.0630 (9) | |
H2A | 0.1562 | −0.0233 | 0.4189 | 0.076* | |
H2B | 0.2391 | 0.0141 | 0.3441 | 0.076* | |
C3 | 0.2851 (3) | −0.0921 (2) | 0.3791 (3) | 0.0714 (10) | |
C4 | 0.2732 (3) | −0.12287 (18) | 0.1898 (2) | 0.0627 (9) | |
C5 | 0.1874 (2) | −0.06051 (17) | 0.1791 (2) | 0.0558 (8) | |
H5A | 0.2267 | −0.0153 | 0.1636 | 0.067* | |
H5B | 0.1362 | −0.0713 | 0.1229 | 0.067* | |
C6 | 0.2288 (3) | −0.1573 (2) | 0.4318 (3) | 0.1054 (14) | |
H6A | 0.1682 | −0.1758 | 0.3898 | 0.158* | |
H6B | 0.1998 | −0.1413 | 0.4951 | 0.158* | |
H6C | 0.2833 | −0.1956 | 0.4435 | 0.158* | |
C7 | 0.3746 (3) | −0.0599 (3) | 0.4535 (3) | 0.1080 (15) | |
H7A | 0.4207 | −0.0989 | 0.4804 | 0.162* | |
H7B | 0.3376 | −0.0353 | 0.5076 | 0.162* | |
H7C | 0.4209 | −0.0253 | 0.4187 | 0.162* | |
C8 | 0.4331 (3) | −0.1640 (2) | 0.2960 (3) | 0.1125 (16) | |
H8A | 0.4884 | −0.1457 | 0.3438 | 0.169* | |
H8B | 0.4678 | −0.1719 | 0.2322 | 0.169* | |
H8C | 0.4030 | −0.2096 | 0.3200 | 0.169* | |
C9 | 0.2120 (3) | −0.19751 (19) | 0.1840 (3) | 0.1016 (14) | |
H9A | 0.2646 | −0.2363 | 0.1991 | 0.152* | |
H9B | 0.1805 | −0.2044 | 0.1173 | 0.152* | |
H9C | 0.1527 | −0.1984 | 0.2320 | 0.152* | |
C10 | 0.3506 (3) | −0.1168 (2) | 0.0988 (3) | 0.0990 (13) | |
H10A | 0.4003 | −0.0755 | 0.1080 | 0.148* | |
H10B | 0.3056 | −0.1099 | 0.0384 | 0.148* | |
H10C | 0.3941 | −0.1610 | 0.0931 | 0.148* | |
C11 | −0.0462 (2) | 0.02021 (17) | 0.3056 (2) | 0.0543 (8) | |
C12 | −0.1247 (2) | 0.08026 (15) | 0.2665 (2) | 0.0493 (8) | |
H12 | −0.1229 | 0.1209 | 0.3150 | 0.059* | |
C13 | −0.0865 (2) | 0.10931 (16) | 0.1655 (2) | 0.0468 (8) | |
C14 | 0.0492 (2) | 0.18507 (14) | 0.0858 (2) | 0.0431 (7) | |
H14 | −0.0052 | 0.1934 | 0.0302 | 0.052* | |
C15 | 0.1334 (2) | 0.12755 (15) | 0.0573 (2) | 0.0473 (8) | |
H15A | 0.0939 | 0.0822 | 0.0414 | 0.057* | |
H15B | 0.1835 | 0.1181 | 0.1148 | 0.057* | |
C16 | 0.2035 (2) | 0.14974 (15) | −0.0324 (2) | 0.0479 (8) | |
C17 | 0.1804 (2) | 0.28400 (15) | 0.0243 (2) | 0.0508 (8) | |
C18 | 0.1102 (2) | 0.25464 (15) | 0.1115 (2) | 0.0495 (8) | |
H18A | 0.1596 | 0.2460 | 0.1696 | 0.059* | |
H18B | 0.0558 | 0.2918 | 0.1300 | 0.059* | |
C19 | 0.1320 (3) | 0.14288 (18) | −0.1304 (2) | 0.0699 (10) | |
H19A | 0.0656 | 0.1727 | −0.1255 | 0.105* | |
H19B | 0.1105 | 0.0924 | −0.1404 | 0.105* | |
H19C | 0.1752 | 0.1592 | −0.1864 | 0.105* | |
C20 | 0.2995 (2) | 0.09311 (17) | −0.0382 (3) | 0.0704 (10) | |
H20A | 0.3380 | 0.0992 | −0.1005 | 0.106* | |
H20B | 0.2688 | 0.0443 | −0.0350 | 0.106* | |
H20C | 0.3516 | 0.1005 | 0.0174 | 0.106* | |
C21 | 0.3302 (3) | 0.24753 (19) | −0.0912 (3) | 0.0873 (12) | |
H21A | 0.3814 | 0.2084 | −0.1062 | 0.131* | |
H21B | 0.3720 | 0.2897 | −0.0678 | 0.131* | |
H21C | 0.2874 | 0.2603 | −0.1511 | 0.131* | |
C22 | 0.2570 (3) | 0.34484 (17) | 0.0697 (3) | 0.0784 (11) | |
H22A | 0.3123 | 0.3230 | 0.1145 | 0.118* | |
H22B | 0.2121 | 0.3791 | 0.1064 | 0.118* | |
H22C | 0.2943 | 0.3701 | 0.0164 | 0.118* | |
C23 | 0.1013 (3) | 0.31988 (17) | −0.0566 (3) | 0.0735 (10) | |
H23A | 0.1447 | 0.3350 | −0.1132 | 0.110* | |
H23B | 0.0650 | 0.3620 | −0.0282 | 0.110* | |
H23C | 0.0453 | 0.2849 | −0.0785 | 0.110* | |
C24 | −0.2440 (2) | 0.05032 (16) | 0.2598 (2) | 0.0596 (9) | |
H24A | −0.2486 | 0.0150 | 0.2051 | 0.071* | |
H24B | −0.2590 | 0.0241 | 0.3218 | 0.071* | |
C25 | −0.3345 (2) | 0.10691 (18) | 0.2432 (3) | 0.0699 (10) | |
H25A | −0.3172 | 0.1360 | 0.1842 | 0.084* | |
H25B | −0.3354 | 0.1398 | 0.3008 | 0.084* | |
C26 | −0.4513 (3) | 0.0722 (2) | 0.2282 (3) | 0.1040 (14) | |
H26A | −0.4529 | 0.0450 | 0.1652 | 0.125* | |
H26B | −0.4631 | 0.0372 | 0.2822 | 0.125* | |
C27 | −0.5421 (3) | 0.1237 (3) | 0.2263 (4) | 0.150 (2) | |
H27A | −0.5422 | 0.1503 | 0.2888 | 0.225* | |
H27B | −0.6122 | 0.0978 | 0.2174 | 0.225* | |
H27C | −0.5329 | 0.1575 | 0.1715 | 0.225* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0530 (13) | 0.0568 (13) | 0.0546 (13) | 0.0093 (10) | 0.0167 (11) | 0.0061 (10) |
O2 | 0.0750 (16) | 0.110 (2) | 0.0733 (17) | 0.0065 (14) | 0.0251 (14) | 0.0392 (16) |
O3 | 0.0491 (12) | 0.0559 (12) | 0.0397 (12) | −0.0090 (10) | 0.0107 (9) | −0.0023 (10) |
O4 | 0.0590 (14) | 0.0953 (17) | 0.0454 (14) | −0.0191 (12) | 0.0024 (11) | −0.0089 (13) |
N1 | 0.0501 (16) | 0.092 (2) | 0.0574 (18) | 0.0143 (15) | −0.0066 (14) | 0.0015 (16) |
N2 | 0.0466 (15) | 0.0598 (17) | 0.0552 (17) | −0.0051 (13) | 0.0161 (13) | 0.0015 (13) |
C1 | 0.0540 (19) | 0.0520 (19) | 0.048 (2) | 0.0030 (16) | 0.0045 (16) | 0.0036 (16) |
C2 | 0.061 (2) | 0.083 (2) | 0.045 (2) | −0.0008 (19) | 0.0054 (17) | −0.0034 (18) |
C3 | 0.056 (2) | 0.104 (3) | 0.054 (2) | 0.003 (2) | −0.0083 (18) | 0.013 (2) |
C4 | 0.053 (2) | 0.072 (2) | 0.063 (2) | 0.0140 (18) | −0.0050 (18) | −0.0073 (18) |
C5 | 0.0567 (19) | 0.067 (2) | 0.0434 (19) | 0.0112 (17) | −0.0030 (16) | −0.0051 (16) |
C6 | 0.095 (3) | 0.125 (3) | 0.096 (3) | 0.014 (3) | 0.007 (3) | 0.052 (3) |
C7 | 0.085 (3) | 0.169 (4) | 0.069 (3) | −0.005 (3) | −0.021 (2) | −0.008 (3) |
C8 | 0.078 (3) | 0.159 (4) | 0.099 (3) | 0.046 (3) | −0.019 (2) | −0.002 (3) |
C9 | 0.096 (3) | 0.070 (3) | 0.137 (4) | 0.020 (2) | −0.030 (3) | −0.026 (3) |
C10 | 0.081 (3) | 0.145 (4) | 0.070 (3) | 0.046 (3) | 0.007 (2) | −0.019 (3) |
C11 | 0.051 (2) | 0.066 (2) | 0.047 (2) | −0.0058 (17) | 0.0126 (17) | −0.0004 (18) |
C12 | 0.0451 (18) | 0.0535 (19) | 0.0499 (19) | −0.0011 (15) | 0.0160 (15) | −0.0053 (16) |
C13 | 0.0407 (18) | 0.055 (2) | 0.045 (2) | 0.0029 (16) | 0.0082 (15) | −0.0023 (16) |
C14 | 0.0447 (17) | 0.0499 (18) | 0.0352 (17) | −0.0035 (15) | 0.0088 (14) | 0.0027 (14) |
C15 | 0.0480 (17) | 0.0481 (18) | 0.0461 (19) | −0.0022 (15) | 0.0055 (15) | 0.0002 (15) |
C16 | 0.0499 (18) | 0.0517 (19) | 0.0426 (18) | −0.0023 (15) | 0.0074 (15) | −0.0024 (15) |
C17 | 0.0511 (18) | 0.0476 (18) | 0.054 (2) | −0.0032 (16) | 0.0061 (16) | 0.0016 (16) |
C18 | 0.0490 (17) | 0.0501 (19) | 0.0496 (19) | 0.0025 (15) | 0.0090 (15) | −0.0026 (15) |
C19 | 0.079 (2) | 0.085 (2) | 0.045 (2) | −0.007 (2) | 0.0040 (18) | −0.0071 (18) |
C20 | 0.062 (2) | 0.072 (2) | 0.078 (2) | 0.0142 (18) | 0.0217 (18) | −0.0079 (19) |
C21 | 0.079 (2) | 0.091 (3) | 0.094 (3) | −0.020 (2) | 0.046 (2) | −0.001 (2) |
C22 | 0.077 (2) | 0.064 (2) | 0.095 (3) | −0.0210 (19) | 0.012 (2) | −0.012 (2) |
C23 | 0.083 (2) | 0.065 (2) | 0.073 (2) | 0.0090 (19) | 0.007 (2) | 0.0176 (19) |
C24 | 0.0525 (19) | 0.066 (2) | 0.061 (2) | −0.0128 (17) | 0.0200 (16) | −0.0091 (17) |
C25 | 0.047 (2) | 0.081 (2) | 0.082 (3) | 0.0013 (18) | 0.0116 (18) | −0.017 (2) |
C26 | 0.055 (2) | 0.117 (3) | 0.140 (4) | 0.005 (2) | 0.005 (2) | −0.027 (3) |
C27 | 0.086 (3) | 0.190 (5) | 0.173 (5) | 0.002 (3) | −0.007 (3) | −0.053 (4) |
O1—C11 | 1.329 (3) | C12—C13 | 1.520 (4) |
O1—C1 | 1.465 (3) | C12—H12 | 0.9800 |
O2—C11 | 1.199 (3) | C14—C18 | 1.492 (3) |
O3—C13 | 1.338 (3) | C14—C15 | 1.501 (3) |
O3—C14 | 1.467 (3) | C14—H14 | 0.9800 |
O4—C13 | 1.202 (3) | C15—C16 | 1.523 (4) |
N1—C8 | 1.466 (4) | C15—H15A | 0.9700 |
N1—C3 | 1.483 (4) | C15—H15B | 0.9700 |
N1—C4 | 1.491 (4) | C16—C20 | 1.539 (4) |
N2—C21 | 1.471 (4) | C16—C19 | 1.540 (4) |
N2—C16 | 1.483 (3) | C17—C18 | 1.537 (4) |
N2—C17 | 1.490 (3) | C17—C22 | 1.544 (4) |
C1—C5 | 1.498 (4) | C17—C23 | 1.552 (4) |
C1—C2 | 1.502 (4) | C18—H18A | 0.9700 |
C1—H1 | 0.9800 | C18—H18B | 0.9700 |
C2—C3 | 1.522 (4) | C19—H19A | 0.9600 |
C2—H2A | 0.9700 | C19—H19B | 0.9600 |
C2—H2B | 0.9700 | C19—H19C | 0.9600 |
C3—C6 | 1.536 (5) | C20—H20A | 0.9600 |
C3—C7 | 1.548 (4) | C20—H20B | 0.9600 |
C4—C5 | 1.528 (4) | C20—H20C | 0.9600 |
C4—C10 | 1.538 (4) | C21—H21A | 0.9600 |
C4—C9 | 1.540 (4) | C21—H21B | 0.9600 |
C5—H5A | 0.9700 | C21—H21C | 0.9600 |
C5—H5B | 0.9700 | C22—H22A | 0.9600 |
C6—H6A | 0.9600 | C22—H22B | 0.9600 |
C6—H6B | 0.9600 | C22—H22C | 0.9600 |
C6—H6C | 0.9600 | C23—H23A | 0.9600 |
C7—H7A | 0.9600 | C23—H23B | 0.9600 |
C7—H7B | 0.9600 | C23—H23C | 0.9600 |
C7—H7C | 0.9600 | C24—C25 | 1.499 (4) |
C8—H8A | 0.9600 | C24—H24A | 0.9700 |
C8—H8B | 0.9600 | C24—H24B | 0.9700 |
C8—H8C | 0.9600 | C25—C26 | 1.533 (4) |
C9—H9A | 0.9600 | C25—H25A | 0.9700 |
C9—H9B | 0.9600 | C25—H25B | 0.9700 |
C9—H9C | 0.9600 | C26—C27 | 1.426 (5) |
C10—H10A | 0.9600 | C26—H26A | 0.9700 |
C10—H10B | 0.9600 | C26—H26B | 0.9700 |
C10—H10C | 0.9600 | C27—H27A | 0.9600 |
C11—C12 | 1.518 (4) | C27—H27B | 0.9600 |
C12—C24 | 1.517 (4) | C27—H27C | 0.9600 |
C11—O1—C1 | 117.8 (2) | C18—C14—C15 | 109.0 (2) |
C13—O3—C14 | 116.4 (2) | O3—C14—H14 | 110.4 |
C8—N1—C3 | 113.7 (3) | C18—C14—H14 | 110.4 |
C8—N1—C4 | 112.1 (3) | C15—C14—H14 | 110.4 |
C3—N1—C4 | 119.7 (2) | C14—C15—C16 | 113.1 (2) |
C21—N2—C16 | 113.2 (2) | C14—C15—H15A | 109.0 |
C21—N2—C17 | 112.8 (2) | C16—C15—H15A | 109.0 |
C16—N2—C17 | 119.6 (2) | C14—C15—H15B | 109.0 |
O1—C1—C5 | 105.8 (2) | C16—C15—H15B | 109.0 |
O1—C1—C2 | 111.5 (2) | H15A—C15—H15B | 107.8 |
C5—C1—C2 | 108.9 (2) | N2—C16—C15 | 108.8 (2) |
O1—C1—H1 | 110.2 | N2—C16—C20 | 108.7 (2) |
C5—C1—H1 | 110.2 | C15—C16—C20 | 106.3 (2) |
C2—C1—H1 | 110.2 | N2—C16—C19 | 115.6 (2) |
C1—C2—C3 | 112.5 (3) | C15—C16—C19 | 109.7 (2) |
C1—C2—H2A | 109.1 | C20—C16—C19 | 107.3 (2) |
C3—C2—H2A | 109.1 | N2—C17—C18 | 108.6 (2) |
C1—C2—H2B | 109.1 | N2—C17—C22 | 108.4 (2) |
C3—C2—H2B | 109.1 | C18—C17—C22 | 106.3 (2) |
H2A—C2—H2B | 107.8 | N2—C17—C23 | 115.5 (2) |
N1—C3—C2 | 108.9 (3) | C18—C17—C23 | 109.6 (2) |
N1—C3—C6 | 115.5 (3) | C22—C17—C23 | 108.0 (2) |
C2—C3—C6 | 110.2 (3) | C14—C18—C17 | 113.0 (2) |
N1—C3—C7 | 107.9 (3) | C14—C18—H18A | 109.0 |
C2—C3—C7 | 106.4 (3) | C17—C18—H18A | 109.0 |
C6—C3—C7 | 107.5 (3) | C14—C18—H18B | 109.0 |
N1—C4—C5 | 108.2 (2) | C17—C18—H18B | 109.0 |
N1—C4—C10 | 108.6 (3) | H18A—C18—H18B | 107.8 |
C5—C4—C10 | 106.5 (3) | C16—C19—H19A | 109.5 |
N1—C4—C9 | 115.3 (3) | C16—C19—H19B | 109.5 |
C5—C4—C9 | 109.6 (2) | H19A—C19—H19B | 109.5 |
C10—C4—C9 | 108.3 (3) | C16—C19—H19C | 109.5 |
C1—C5—C4 | 113.2 (2) | H19A—C19—H19C | 109.5 |
C1—C5—H5A | 108.9 | H19B—C19—H19C | 109.5 |
C4—C5—H5A | 108.9 | C16—C20—H20A | 109.5 |
C1—C5—H5B | 108.9 | C16—C20—H20B | 109.5 |
C4—C5—H5B | 108.9 | H20A—C20—H20B | 109.5 |
H5A—C5—H5B | 107.8 | C16—C20—H20C | 109.5 |
C3—C6—H6A | 109.5 | H20A—C20—H20C | 109.5 |
C3—C6—H6B | 109.5 | H20B—C20—H20C | 109.5 |
H6A—C6—H6B | 109.5 | N2—C21—H21A | 109.5 |
C3—C6—H6C | 109.5 | N2—C21—H21B | 109.5 |
H6A—C6—H6C | 109.5 | H21A—C21—H21B | 109.5 |
H6B—C6—H6C | 109.5 | N2—C21—H21C | 109.5 |
C3—C7—H7A | 109.5 | H21A—C21—H21C | 109.5 |
C3—C7—H7B | 109.5 | H21B—C21—H21C | 109.5 |
H7A—C7—H7B | 109.5 | C17—C22—H22A | 109.5 |
C3—C7—H7C | 109.5 | C17—C22—H22B | 109.5 |
H7A—C7—H7C | 109.5 | H22A—C22—H22B | 109.5 |
H7B—C7—H7C | 109.5 | C17—C22—H22C | 109.5 |
N1—C8—H8A | 109.5 | H22A—C22—H22C | 109.5 |
N1—C8—H8B | 109.5 | H22B—C22—H22C | 109.5 |
H8A—C8—H8B | 109.5 | C17—C23—H23A | 109.5 |
N1—C8—H8C | 109.5 | C17—C23—H23B | 109.5 |
H8A—C8—H8C | 109.5 | H23A—C23—H23B | 109.5 |
H8B—C8—H8C | 109.5 | C17—C23—H23C | 109.5 |
C4—C9—H9A | 109.5 | H23A—C23—H23C | 109.5 |
C4—C9—H9B | 109.5 | H23B—C23—H23C | 109.5 |
H9A—C9—H9B | 109.5 | C25—C24—C12 | 115.3 (2) |
C4—C9—H9C | 109.5 | C25—C24—H24A | 108.5 |
H9A—C9—H9C | 109.5 | C12—C24—H24A | 108.5 |
H9B—C9—H9C | 109.5 | C25—C24—H24B | 108.5 |
C4—C10—H10A | 109.5 | C12—C24—H24B | 108.5 |
C4—C10—H10B | 109.5 | H24A—C24—H24B | 107.5 |
H10A—C10—H10B | 109.5 | C24—C25—C26 | 112.3 (3) |
C4—C10—H10C | 109.5 | C24—C25—H25A | 109.1 |
H10A—C10—H10C | 109.5 | C26—C25—H25A | 109.1 |
H10B—C10—H10C | 109.5 | C24—C25—H25B | 109.1 |
O2—C11—O1 | 124.3 (3) | C26—C25—H25B | 109.1 |
O2—C11—C12 | 123.3 (3) | H25A—C25—H25B | 107.9 |
O1—C11—C12 | 112.4 (3) | C27—C26—C25 | 114.4 (4) |
C24—C12—C11 | 109.1 (2) | C27—C26—H26A | 108.7 |
C24—C12—C13 | 111.8 (2) | C25—C26—H26A | 108.7 |
C11—C12—C13 | 110.9 (2) | C27—C26—H26B | 108.7 |
C24—C12—H12 | 108.3 | C25—C26—H26B | 108.7 |
C11—C12—H12 | 108.3 | H26A—C26—H26B | 107.6 |
C13—C12—H12 | 108.3 | C26—C27—H27A | 109.5 |
O4—C13—O3 | 124.3 (3) | C26—C27—H27B | 109.5 |
O4—C13—C12 | 124.1 (3) | H27A—C27—H27B | 109.5 |
O3—C13—C12 | 111.6 (3) | C26—C27—H27C | 109.5 |
O3—C14—C18 | 106.6 (2) | H27A—C27—H27C | 109.5 |
O3—C14—C15 | 109.9 (2) | H27B—C27—H27C | 109.5 |
C11—O1—C1—C5 | 160.6 (2) | C24—C12—C13—O4 | −28.1 (4) |
C11—O1—C1—C2 | −81.1 (3) | C11—C12—C13—O4 | 93.9 (3) |
O1—C1—C2—C3 | −175.8 (2) | C24—C12—C13—O3 | 152.5 (2) |
C5—C1—C2—C3 | −59.4 (3) | C11—C12—C13—O3 | −85.5 (3) |
C8—N1—C3—C2 | 175.2 (3) | C13—O3—C14—C18 | 167.3 (2) |
C4—N1—C3—C2 | −48.4 (4) | C13—O3—C14—C15 | −74.8 (3) |
C8—N1—C3—C6 | −60.2 (4) | O3—C14—C15—C16 | −175.8 (2) |
C4—N1—C3—C6 | 76.1 (4) | C18—C14—C15—C16 | −59.3 (3) |
C8—N1—C3—C7 | 60.1 (4) | C21—N2—C16—C15 | 175.3 (2) |
C4—N1—C3—C7 | −163.6 (3) | C17—N2—C16—C15 | −47.9 (3) |
C1—C2—C3—N1 | 52.4 (3) | C21—N2—C16—C20 | 60.0 (3) |
C1—C2—C3—C6 | −75.3 (4) | C17—N2—C16—C20 | −163.3 (2) |
C1—C2—C3—C7 | 168.4 (3) | C21—N2—C16—C19 | −60.7 (3) |
C8—N1—C4—C5 | −175.2 (3) | C17—N2—C16—C19 | 76.0 (3) |
C3—N1—C4—C5 | 47.8 (4) | C14—C15—C16—N2 | 52.1 (3) |
C8—N1—C4—C10 | −60.0 (4) | C14—C15—C16—C20 | 169.0 (2) |
C3—N1—C4—C10 | 162.9 (3) | C14—C15—C16—C19 | −75.2 (3) |
C8—N1—C4—C9 | 61.7 (4) | C21—N2—C17—C18 | −175.6 (2) |
C3—N1—C4—C9 | −75.3 (4) | C16—N2—C17—C18 | 47.4 (3) |
O1—C1—C5—C4 | 179.5 (2) | C21—N2—C17—C22 | −60.6 (3) |
C2—C1—C5—C4 | 59.4 (3) | C16—N2—C17—C22 | 162.5 (2) |
N1—C4—C5—C1 | −51.7 (3) | C21—N2—C17—C23 | 60.8 (3) |
C10—C4—C5—C1 | −168.3 (3) | C16—N2—C17—C23 | −76.1 (3) |
C9—C4—C5—C1 | 74.7 (3) | O3—C14—C18—C17 | 177.4 (2) |
C1—O1—C11—O2 | 5.9 (4) | C15—C14—C18—C17 | 58.8 (3) |
C1—O1—C11—C12 | −173.4 (2) | N2—C17—C18—C14 | −51.4 (3) |
O2—C11—C12—C24 | −48.8 (4) | C22—C17—C18—C14 | −167.9 (2) |
O1—C11—C12—C24 | 130.5 (3) | C23—C17—C18—C14 | 75.6 (3) |
O2—C11—C12—C13 | −172.4 (3) | C11—C12—C24—C25 | 167.8 (3) |
O1—C11—C12—C13 | 7.0 (3) | C13—C12—C24—C25 | −69.2 (3) |
C14—O3—C13—O4 | −10.2 (4) | C12—C24—C25—C26 | 175.1 (3) |
C14—O3—C13—C12 | 169.1 (2) | C24—C25—C26—C27 | 171.5 (4) |