Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805025961/ww6399sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805025961/ww6399Isup2.hkl |
CCDC reference: 284005
Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); 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.
C33H53NO2 | Dx = 1.024 Mg m−3 |
Mr = 495.76 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43 | Cell parameters from 3052 reflections |
Hall symbol: P 4cw | θ = 2.4–19.6° |
a = 15.822 (4) Å | µ = 0.06 mm−1 |
c = 12.844 (4) Å | T = 294 K |
V = 3215.4 (15) Å3 | Block, colourless |
Z = 4 | 0.24 × 0.22 × 0.18 mm |
F(000) = 1096 |
Bruker SMART CCD area-detector diffractometer | 3601 independent reflections |
Radiation source: fine-focus sealed tube | 1888 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.128 |
φ and ω scans | θmax = 27.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −19→18 |
Tmin = 0.972, Tmax = 0.989 | k = −20→15 |
18244 measured reflections | l = −16→15 |
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) = 0.164 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0563P)2 + 0.9914P] where P = (Fo2 + 2Fc2)/3 |
3601 reflections | (Δ/σ)max < 0.001 |
325 parameters | Δρmax = 0.21 e Å−3 |
1 restraint | Δρmin = −0.15 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 | ||
N1 | 0.0680 (2) | 0.4351 (2) | 1.0435 (3) | 0.0424 (8) | |
O1 | 0.4511 (2) | 0.3339 (2) | 0.9203 (3) | 0.0842 (12) | |
H1A | 0.4976 | 0.3683 | 0.8936 | 0.101* | |
O2 | −0.1522 (2) | 0.1003 (2) | 0.9501 (3) | 0.0741 (10) | |
H2A | −0.1186 | 0.0424 | 0.9669 | 0.089* | |
C1 | 0.3713 (3) | 0.3447 (3) | 0.9619 (4) | 0.0536 (12) | |
C2 | 0.3600 (3) | 0.3284 (3) | 1.0693 (4) | 0.0469 (11) | |
C3 | 0.2799 (3) | 0.3426 (2) | 1.1105 (3) | 0.0431 (10) | |
H3A | 0.2713 | 0.3334 | 1.1812 | 0.052* | |
C4 | 0.2121 (2) | 0.3699 (2) | 1.0498 (3) | 0.0423 (10) | |
C5 | 0.2262 (3) | 0.3824 (3) | 0.9444 (4) | 0.0493 (11) | |
H5A | 0.1810 | 0.3991 | 0.9030 | 0.059* | |
C6 | 0.3045 (3) | 0.3710 (3) | 0.8977 (4) | 0.0525 (12) | |
C7 | 0.4331 (3) | 0.2954 (3) | 1.1389 (4) | 0.0531 (12) | |
C8 | 0.5017 (3) | 0.3625 (4) | 1.1496 (5) | 0.0768 (16) | |
H8A | 0.5464 | 0.3413 | 1.1928 | 0.115* | |
H8B | 0.4781 | 0.4124 | 1.1807 | 0.115* | |
H8C | 0.5237 | 0.3762 | 1.0820 | 0.115* | |
C9 | 0.4703 (3) | 0.2124 (3) | 1.0947 (5) | 0.0766 (16) | |
H9A | 0.5152 | 0.1931 | 1.1391 | 0.115* | |
H9B | 0.4920 | 0.2224 | 1.0260 | 0.115* | |
H9C | 0.4269 | 0.1702 | 1.0916 | 0.115* | |
C10 | 0.4015 (3) | 0.2735 (3) | 1.2486 (4) | 0.0625 (14) | |
H10A | 0.4478 | 0.2532 | 1.2899 | 0.094* | |
H10B | 0.3588 | 0.2306 | 1.2441 | 0.094* | |
H10C | 0.3781 | 0.3231 | 1.2805 | 0.094* | |
C11 | 0.3154 (3) | 0.3841 (3) | 0.7789 (4) | 0.0598 (13) | |
C12 | 0.3788 (4) | 0.4563 (4) | 0.7567 (5) | 0.093 (2) | |
H12A | 0.3851 | 0.4632 | 0.6828 | 0.139* | |
H12B | 0.4326 | 0.4425 | 0.7868 | 0.139* | |
H12C | 0.3582 | 0.5079 | 0.7866 | 0.139* | |
C13 | 0.3455 (5) | 0.3014 (4) | 0.7257 (5) | 0.096 (2) | |
H13A | 0.3060 | 0.2568 | 0.7404 | 0.144* | |
H13B | 0.4002 | 0.2861 | 0.7520 | 0.144* | |
H13C | 0.3488 | 0.3099 | 0.6518 | 0.144* | |
C14 | 0.2328 (4) | 0.4076 (4) | 0.7253 (5) | 0.093 (2) | |
H14A | 0.1918 | 0.3640 | 0.7371 | 0.139* | |
H14B | 0.2424 | 0.4137 | 0.6518 | 0.139* | |
H14C | 0.2122 | 0.4600 | 0.7531 | 0.139* | |
C15 | 0.1253 (2) | 0.3779 (3) | 1.0989 (4) | 0.0464 (10) | |
H15A | 0.0996 | 0.3223 | 1.1019 | 0.056* | |
H15B | 0.1319 | 0.3979 | 1.1698 | 0.056* | |
C16 | 0.0915 (3) | 0.5234 (3) | 1.0646 (5) | 0.0613 (14) | |
H16A | 0.1520 | 0.5294 | 1.0556 | 0.074* | |
H16B | 0.0786 | 0.5361 | 1.1368 | 0.074* | |
C17 | 0.0474 (4) | 0.5881 (3) | 0.9961 (5) | 0.0792 (17) | |
H17A | −0.0129 | 0.5861 | 1.0096 | 0.095* | |
H17B | 0.0673 | 0.6441 | 1.0144 | 0.095* | |
C18 | 0.0621 (5) | 0.5738 (5) | 0.8841 (6) | 0.116 (3) | |
H18A | 0.0332 | 0.6165 | 0.8446 | 0.174* | |
H18B | 0.0411 | 0.5191 | 0.8649 | 0.174* | |
H18C | 0.1216 | 0.5767 | 0.8699 | 0.174* | |
C19 | −0.0197 (3) | 0.4182 (3) | 1.0735 (4) | 0.0516 (12) | |
H19A | −0.0560 | 0.4602 | 1.0416 | 0.062* | |
H19B | −0.0249 | 0.4239 | 1.1484 | 0.062* | |
C20 | −0.1162 (3) | 0.1763 (3) | 0.9785 (4) | 0.0511 (12) | |
C21 | −0.0716 (3) | 0.2260 (3) | 0.9060 (3) | 0.0464 (11) | |
C22 | −0.0408 (3) | 0.3029 (3) | 0.9400 (4) | 0.0509 (12) | |
H22A | −0.0127 | 0.3373 | 0.8926 | 0.061* | |
C23 | −0.0500 (3) | 0.3312 (3) | 1.0420 (3) | 0.0445 (10) | |
C24 | −0.0921 (3) | 0.2795 (3) | 1.1113 (4) | 0.0503 (11) | |
H24A | −0.0977 | 0.2975 | 1.1799 | 0.060* | |
C25 | −0.1266 (3) | 0.2014 (3) | 1.0835 (4) | 0.0488 (11) | |
C26 | −0.0602 (3) | 0.1983 (3) | 0.7905 (4) | 0.0520 (11) | |
C27 | −0.1459 (3) | 0.1941 (4) | 0.7340 (4) | 0.0827 (18) | |
H27A | −0.1372 | 0.1769 | 0.6631 | 0.124* | |
H27B | −0.1721 | 0.2488 | 0.7354 | 0.124* | |
H27C | −0.1818 | 0.1539 | 0.7684 | 0.124* | |
C28 | −0.0141 (4) | 0.1127 (3) | 0.7823 (5) | 0.0780 (16) | |
H28A | −0.0083 | 0.0974 | 0.7103 | 0.117* | |
H28B | −0.0462 | 0.0701 | 0.8180 | 0.117* | |
H28C | 0.0408 | 0.1173 | 0.8135 | 0.117* | |
C29 | −0.0058 (4) | 0.2623 (4) | 0.7313 (5) | 0.0895 (19) | |
H29A | 0.0004 | 0.2443 | 0.6603 | 0.134* | |
H29B | 0.0489 | 0.2660 | 0.7633 | 0.134* | |
H29C | −0.0326 | 0.3167 | 0.7331 | 0.134* | |
C30 | −0.1752 (3) | 0.1467 (3) | 1.1631 (4) | 0.0608 (13) | |
C31 | −0.2678 (4) | 0.1367 (5) | 1.1283 (5) | 0.102 (2) | |
H31A | −0.2978 | 0.1029 | 1.1782 | 0.153* | |
H31B | −0.2696 | 0.1096 | 1.0615 | 0.153* | |
H31C | −0.2938 | 0.1914 | 1.1235 | 0.153* | |
C32 | −0.1328 (4) | 0.0605 (3) | 1.1769 (5) | 0.0857 (18) | |
H32D | −0.1172 | 0.0529 | 1.2486 | 0.129* | |
H32E | −0.0831 | 0.0578 | 1.1341 | 0.129* | |
H32F | −0.1713 | 0.0166 | 1.1567 | 0.129* | |
C33 | −0.1768 (4) | 0.1885 (4) | 1.2714 (4) | 0.0867 (19) | |
H33A | −0.2078 | 0.1534 | 1.3189 | 0.130* | |
H33B | −0.2037 | 0.2428 | 1.2666 | 0.130* | |
H33C | −0.1200 | 0.1955 | 1.2962 | 0.130* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.039 (2) | 0.039 (2) | 0.050 (2) | −0.0018 (15) | −0.0018 (16) | 0.0030 (16) |
O1 | 0.050 (2) | 0.107 (3) | 0.096 (3) | 0.0014 (18) | 0.029 (2) | 0.004 (2) |
O2 | 0.092 (3) | 0.060 (2) | 0.071 (2) | −0.0280 (19) | −0.001 (2) | −0.0064 (19) |
C1 | 0.039 (3) | 0.058 (3) | 0.064 (3) | −0.005 (2) | 0.008 (2) | 0.001 (2) |
C2 | 0.038 (2) | 0.046 (3) | 0.057 (3) | −0.0007 (19) | −0.004 (2) | −0.002 (2) |
C3 | 0.044 (3) | 0.044 (2) | 0.041 (2) | −0.0024 (19) | −0.001 (2) | 0.000 (2) |
C4 | 0.035 (2) | 0.042 (2) | 0.049 (3) | −0.0008 (18) | 0.001 (2) | 0.003 (2) |
C5 | 0.047 (3) | 0.050 (3) | 0.051 (3) | 0.002 (2) | −0.001 (2) | 0.006 (2) |
C6 | 0.052 (3) | 0.050 (3) | 0.056 (3) | −0.002 (2) | 0.010 (2) | 0.000 (2) |
C7 | 0.043 (3) | 0.049 (3) | 0.067 (3) | 0.005 (2) | −0.008 (2) | −0.004 (2) |
C8 | 0.052 (3) | 0.092 (4) | 0.086 (4) | −0.021 (3) | −0.011 (3) | −0.002 (3) |
C9 | 0.071 (4) | 0.069 (4) | 0.090 (4) | 0.021 (3) | −0.002 (3) | −0.003 (3) |
C10 | 0.056 (3) | 0.068 (3) | 0.063 (3) | 0.002 (2) | −0.011 (3) | 0.006 (3) |
C11 | 0.068 (3) | 0.061 (3) | 0.051 (3) | −0.004 (2) | 0.012 (3) | 0.004 (2) |
C12 | 0.112 (5) | 0.092 (4) | 0.075 (4) | −0.023 (4) | 0.017 (4) | 0.016 (3) |
C13 | 0.139 (6) | 0.084 (4) | 0.065 (4) | 0.009 (4) | 0.008 (4) | −0.009 (3) |
C14 | 0.097 (5) | 0.133 (6) | 0.048 (3) | 0.006 (4) | 0.003 (3) | 0.025 (4) |
C15 | 0.040 (2) | 0.051 (3) | 0.048 (3) | 0.0015 (19) | −0.003 (2) | 0.008 (2) |
C16 | 0.060 (3) | 0.043 (3) | 0.081 (4) | −0.004 (2) | −0.007 (3) | 0.004 (3) |
C17 | 0.097 (4) | 0.057 (3) | 0.084 (5) | 0.008 (3) | −0.002 (3) | 0.017 (3) |
C18 | 0.158 (7) | 0.111 (6) | 0.079 (5) | 0.035 (5) | −0.006 (5) | 0.016 (4) |
C19 | 0.045 (3) | 0.058 (3) | 0.051 (3) | 0.000 (2) | 0.004 (2) | −0.005 (2) |
C20 | 0.052 (3) | 0.053 (3) | 0.048 (3) | −0.009 (2) | −0.005 (2) | −0.003 (2) |
C21 | 0.042 (2) | 0.055 (3) | 0.042 (3) | −0.003 (2) | −0.002 (2) | −0.002 (2) |
C22 | 0.045 (3) | 0.060 (3) | 0.047 (3) | −0.004 (2) | 0.004 (2) | 0.000 (2) |
C23 | 0.040 (2) | 0.052 (3) | 0.042 (3) | −0.0039 (19) | −0.002 (2) | −0.004 (2) |
C24 | 0.044 (3) | 0.069 (3) | 0.039 (3) | −0.004 (2) | 0.001 (2) | −0.002 (2) |
C25 | 0.042 (2) | 0.059 (3) | 0.045 (3) | −0.009 (2) | −0.002 (2) | 0.002 (2) |
C26 | 0.052 (3) | 0.061 (3) | 0.044 (3) | 0.006 (2) | −0.001 (2) | −0.003 (2) |
C27 | 0.071 (4) | 0.126 (5) | 0.052 (3) | 0.017 (3) | −0.014 (3) | −0.014 (3) |
C28 | 0.088 (4) | 0.080 (4) | 0.066 (4) | 0.024 (3) | −0.002 (3) | −0.016 (3) |
C29 | 0.117 (5) | 0.098 (4) | 0.053 (4) | −0.016 (4) | 0.025 (3) | −0.010 (3) |
C30 | 0.060 (3) | 0.074 (3) | 0.049 (3) | −0.013 (2) | 0.006 (2) | 0.011 (3) |
C31 | 0.069 (4) | 0.148 (6) | 0.088 (5) | −0.040 (4) | 0.004 (3) | 0.034 (4) |
C32 | 0.114 (5) | 0.070 (4) | 0.074 (4) | 0.002 (3) | 0.008 (4) | 0.018 (3) |
C33 | 0.103 (5) | 0.105 (5) | 0.052 (4) | −0.011 (3) | 0.021 (3) | 0.013 (3) |
N1—C19 | 1.465 (5) | C16—H16A | 0.9700 |
N1—C15 | 1.466 (5) | C16—H16B | 0.9700 |
N1—C16 | 1.471 (5) | C17—C18 | 1.474 (10) |
O1—C1 | 1.381 (5) | C17—H17A | 0.9700 |
O1—H1A | 0.9787 | C17—H17B | 0.9700 |
O2—C20 | 1.380 (5) | C18—H18A | 0.9600 |
O2—H2A | 1.0810 | C18—H18B | 0.9600 |
C1—C6 | 1.404 (7) | C18—H18C | 0.9600 |
C1—C2 | 1.414 (7) | C19—C23 | 1.512 (6) |
C2—C3 | 1.392 (6) | C19—H19A | 0.9700 |
C2—C7 | 1.552 (6) | C19—H19B | 0.9700 |
C3—C4 | 1.395 (6) | C20—C21 | 1.408 (6) |
C3—H3A | 0.9300 | C20—C25 | 1.415 (7) |
C4—C5 | 1.386 (6) | C21—C22 | 1.382 (6) |
C4—C15 | 1.516 (6) | C21—C26 | 1.557 (7) |
C5—C6 | 1.389 (6) | C22—C23 | 1.391 (6) |
C5—H5A | 0.9300 | C22—H22A | 0.9300 |
C6—C11 | 1.549 (7) | C23—C24 | 1.381 (6) |
C7—C8 | 1.525 (6) | C24—C25 | 1.397 (6) |
C7—C10 | 1.535 (7) | C24—H24A | 0.9300 |
C7—C9 | 1.547 (7) | C25—C30 | 1.545 (6) |
C8—H8A | 0.9600 | C26—C29 | 1.531 (7) |
C8—H8B | 0.9600 | C26—C27 | 1.539 (7) |
C8—H8C | 0.9600 | C26—C28 | 1.542 (6) |
C9—H9A | 0.9600 | C27—H27A | 0.9600 |
C9—H9B | 0.9600 | C27—H27B | 0.9600 |
C9—H9C | 0.9600 | C27—H27C | 0.9600 |
C10—H10A | 0.9600 | C28—H28A | 0.9600 |
C10—H10B | 0.9600 | C28—H28B | 0.9600 |
C10—H10C | 0.9600 | C28—H28C | 0.9600 |
C11—C14 | 1.524 (7) | C29—H29A | 0.9600 |
C11—C12 | 1.547 (7) | C29—H29B | 0.9600 |
C11—C13 | 1.551 (7) | C29—H29C | 0.9600 |
C12—H12A | 0.9600 | C30—C32 | 1.530 (7) |
C12—H12B | 0.9600 | C30—C31 | 1.540 (7) |
C12—H12C | 0.9600 | C30—C33 | 1.541 (7) |
C13—H13A | 0.9600 | C31—H31A | 0.9600 |
C13—H13B | 0.9600 | C31—H31B | 0.9600 |
C13—H13C | 0.9600 | C31—H31C | 0.9600 |
C14—H14A | 0.9600 | C32—H32D | 0.9600 |
C14—H14B | 0.9600 | C32—H32E | 0.9600 |
C14—H14C | 0.9600 | C32—H32F | 0.9600 |
C15—H15A | 0.9700 | C33—H33A | 0.9600 |
C15—H15B | 0.9700 | C33—H33B | 0.9600 |
C16—C17 | 1.519 (7) | C33—H33C | 0.9600 |
C19—N1—C15 | 110.2 (3) | C18—C17—H17A | 109.0 |
C19—N1—C16 | 111.4 (3) | C16—C17—H17A | 109.0 |
C15—N1—C16 | 110.0 (3) | C18—C17—H17B | 109.0 |
C1—O1—H1A | 139.0 | C16—C17—H17B | 109.0 |
C20—O2—H2A | 118.8 | H17A—C17—H17B | 107.8 |
O1—C1—C6 | 119.8 (5) | C17—C18—H18A | 109.5 |
O1—C1—C2 | 118.0 (4) | C17—C18—H18B | 109.5 |
C6—C1—C2 | 122.1 (4) | H18A—C18—H18B | 109.5 |
C3—C2—C1 | 117.2 (4) | C17—C18—H18C | 109.5 |
C3—C2—C7 | 120.9 (4) | H18A—C18—H18C | 109.5 |
C1—C2—C7 | 121.9 (4) | H18B—C18—H18C | 109.5 |
C2—C3—C4 | 122.6 (4) | N1—C19—C23 | 113.4 (3) |
C2—C3—H3A | 118.7 | N1—C19—H19A | 108.9 |
C4—C3—H3A | 118.7 | C23—C19—H19A | 108.9 |
C5—C4—C3 | 117.8 (4) | N1—C19—H19B | 108.9 |
C5—C4—C15 | 122.7 (4) | C23—C19—H19B | 108.9 |
C3—C4—C15 | 119.4 (4) | H19A—C19—H19B | 107.7 |
C4—C5—C6 | 123.2 (4) | O2—C20—C21 | 121.2 (4) |
C4—C5—H5A | 118.4 | O2—C20—C25 | 116.7 (4) |
C6—C5—H5A | 118.4 | C21—C20—C25 | 122.1 (4) |
C5—C6—C1 | 117.2 (4) | C22—C21—C20 | 117.3 (4) |
C5—C6—C11 | 120.5 (4) | C22—C21—C26 | 120.5 (4) |
C1—C6—C11 | 122.3 (4) | C20—C21—C26 | 122.1 (4) |
C8—C7—C10 | 107.8 (4) | C21—C22—C23 | 123.0 (4) |
C8—C7—C9 | 110.7 (4) | C21—C22—H22A | 118.5 |
C10—C7—C9 | 105.6 (4) | C23—C22—H22A | 118.5 |
C8—C7—C2 | 110.3 (4) | C24—C23—C22 | 117.8 (4) |
C10—C7—C2 | 111.2 (4) | C24—C23—C19 | 121.3 (4) |
C9—C7—C2 | 111.0 (4) | C22—C23—C19 | 120.8 (4) |
C7—C8—H8A | 109.5 | C23—C24—C25 | 123.2 (4) |
C7—C8—H8B | 109.5 | C23—C24—H24A | 118.4 |
H8A—C8—H8B | 109.5 | C25—C24—H24A | 118.4 |
C7—C8—H8C | 109.5 | C24—C25—C20 | 116.5 (4) |
H8A—C8—H8C | 109.5 | C24—C25—C30 | 121.4 (4) |
H8B—C8—H8C | 109.5 | C20—C25—C30 | 122.1 (4) |
C7—C9—H9A | 109.5 | C29—C26—C27 | 106.8 (5) |
C7—C9—H9B | 109.5 | C29—C26—C28 | 106.4 (4) |
H9A—C9—H9B | 109.5 | C27—C26—C28 | 110.3 (4) |
C7—C9—H9C | 109.5 | C29—C26—C21 | 110.6 (4) |
H9A—C9—H9C | 109.5 | C27—C26—C21 | 111.1 (4) |
H9B—C9—H9C | 109.5 | C28—C26—C21 | 111.5 (4) |
C7—C10—H10A | 109.5 | C26—C27—H27A | 109.5 |
C7—C10—H10B | 109.5 | C26—C27—H27B | 109.5 |
H10A—C10—H10B | 109.5 | H27A—C27—H27B | 109.5 |
C7—C10—H10C | 109.5 | C26—C27—H27C | 109.5 |
H10A—C10—H10C | 109.5 | H27A—C27—H27C | 109.5 |
H10B—C10—H10C | 109.5 | H27B—C27—H27C | 109.5 |
C14—C11—C12 | 107.0 (5) | C26—C28—H28A | 109.5 |
C14—C11—C6 | 112.5 (4) | C26—C28—H28B | 109.5 |
C12—C11—C6 | 110.6 (4) | H28A—C28—H28B | 109.5 |
C14—C11—C13 | 105.7 (5) | C26—C28—H28C | 109.5 |
C12—C11—C13 | 110.1 (5) | H28A—C28—H28C | 109.5 |
C6—C11—C13 | 110.8 (4) | H28B—C28—H28C | 109.5 |
C11—C12—H12A | 109.5 | C26—C29—H29A | 109.5 |
C11—C12—H12B | 109.5 | C26—C29—H29B | 109.5 |
H12A—C12—H12B | 109.5 | H29A—C29—H29B | 109.5 |
C11—C12—H12C | 109.5 | C26—C29—H29C | 109.5 |
H12A—C12—H12C | 109.5 | H29A—C29—H29C | 109.5 |
H12B—C12—H12C | 109.5 | H29B—C29—H29C | 109.5 |
C11—C13—H13A | 109.5 | C32—C30—C31 | 111.1 (5) |
C11—C13—H13B | 109.5 | C32—C30—C33 | 106.6 (5) |
H13A—C13—H13B | 109.5 | C31—C30—C33 | 106.9 (5) |
C11—C13—H13C | 109.5 | C32—C30—C25 | 110.9 (4) |
H13A—C13—H13C | 109.5 | C31—C30—C25 | 109.8 (4) |
H13B—C13—H13C | 109.5 | C33—C30—C25 | 111.4 (4) |
C11—C14—H14A | 109.5 | C30—C31—H31A | 109.5 |
C11—C14—H14B | 109.5 | C30—C31—H31B | 109.5 |
H14A—C14—H14B | 109.5 | H31A—C31—H31B | 109.5 |
C11—C14—H14C | 109.5 | C30—C31—H31C | 109.5 |
H14A—C14—H14C | 109.5 | H31A—C31—H31C | 109.5 |
H14B—C14—H14C | 109.5 | H31B—C31—H31C | 109.5 |
N1—C15—C4 | 114.2 (3) | C30—C32—H32D | 109.6 |
N1—C15—H15A | 108.7 | C30—C32—H32E | 109.3 |
C4—C15—H15A | 108.7 | H32D—C32—H32E | 109.5 |
N1—C15—H15B | 108.7 | C30—C32—H32F | 109.5 |
C4—C15—H15B | 108.7 | H32D—C32—H32F | 109.5 |
H15A—C15—H15B | 107.6 | H32E—C32—H32F | 109.5 |
N1—C16—C17 | 114.6 (4) | C30—C33—H33A | 109.5 |
N1—C16—H16A | 108.6 | C30—C33—H33B | 109.5 |
C17—C16—H16A | 108.6 | H33A—C33—H33B | 109.5 |
N1—C16—H16B | 108.6 | C30—C33—H33C | 109.5 |
C17—C16—H16B | 108.6 | H33A—C33—H33C | 109.5 |
H16A—C16—H16B | 107.6 | H33B—C33—H33C | 109.5 |
C18—C17—C16 | 113.0 (5) | ||
O1—C1—C2—C3 | 177.7 (4) | N1—C16—C17—C18 | −57.6 (8) |
C6—C1—C2—C3 | −2.3 (7) | C15—N1—C19—C23 | −64.3 (5) |
O1—C1—C2—C7 | −2.8 (6) | C16—N1—C19—C23 | 173.3 (4) |
C6—C1—C2—C7 | 177.1 (4) | O2—C20—C21—C22 | 177.2 (4) |
C1—C2—C3—C4 | 1.4 (6) | C25—C20—C21—C22 | −2.7 (7) |
C7—C2—C3—C4 | −178.1 (4) | O2—C20—C21—C26 | −0.1 (7) |
C2—C3—C4—C5 | 0.6 (6) | C25—C20—C21—C26 | 180.0 (4) |
C2—C3—C4—C15 | 175.7 (4) | C20—C21—C22—C23 | 1.9 (6) |
C3—C4—C5—C6 | −1.7 (6) | C26—C21—C22—C23 | 179.3 (4) |
C15—C4—C5—C6 | −176.6 (4) | C21—C22—C23—C24 | −0.1 (6) |
C4—C5—C6—C1 | 0.8 (7) | C21—C22—C23—C19 | −176.3 (4) |
C4—C5—C6—C11 | 178.6 (4) | N1—C19—C23—C24 | 132.4 (4) |
O1—C1—C6—C5 | −178.8 (4) | N1—C19—C23—C22 | −51.5 (6) |
C2—C1—C6—C5 | 1.3 (7) | C22—C23—C24—C25 | −1.0 (7) |
O1—C1—C6—C11 | 3.4 (7) | C19—C23—C24—C25 | 175.2 (4) |
C2—C1—C6—C11 | −176.5 (4) | C23—C24—C25—C20 | 0.3 (7) |
C3—C2—C7—C8 | −113.7 (5) | C23—C24—C25—C30 | −178.4 (4) |
C1—C2—C7—C8 | 66.9 (6) | O2—C20—C25—C24 | −178.3 (4) |
C3—C2—C7—C10 | 5.9 (6) | C21—C20—C25—C24 | 1.6 (7) |
C1—C2—C7—C10 | −173.5 (4) | O2—C20—C25—C30 | 0.4 (7) |
C3—C2—C7—C9 | 123.2 (5) | C21—C20—C25—C30 | −179.7 (4) |
C1—C2—C7—C9 | −56.2 (6) | C22—C21—C26—C29 | 5.4 (6) |
C5—C6—C11—C14 | −1.2 (7) | C20—C21—C26—C29 | −177.4 (5) |
C1—C6—C11—C14 | 176.6 (5) | C22—C21—C26—C27 | −113.1 (5) |
C5—C6—C11—C12 | 118.5 (5) | C20—C21—C26—C27 | 64.2 (6) |
C1—C6—C11—C12 | −63.8 (6) | C22—C21—C26—C28 | 123.5 (5) |
C5—C6—C11—C13 | −119.2 (5) | C20—C21—C26—C28 | −59.3 (6) |
C1—C6—C11—C13 | 58.6 (6) | C24—C25—C30—C32 | −120.2 (5) |
C19—N1—C15—C4 | 161.2 (4) | C20—C25—C30—C32 | 61.2 (6) |
C16—N1—C15—C4 | −75.6 (5) | C24—C25—C30—C31 | 116.7 (5) |
C5—C4—C15—N1 | −27.1 (6) | C20—C25—C30—C31 | −61.9 (6) |
C3—C4—C15—N1 | 158.1 (4) | C24—C25—C30—C33 | −1.6 (6) |
C19—N1—C16—C17 | −68.5 (6) | C20—C25—C30—C33 | 179.9 (5) |
C15—N1—C16—C17 | 169.1 (4) |