Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807004394/bv2040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807004394/bv2040Isup2.hkl |
CCDC reference: 624625
Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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, 2002); software used to prepare material for publication: SHELXL97.
C18H17NO2 | F(000) = 592 |
Mr = 279.33 | Dx = 1.269 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1848 reflections |
a = 9.4120 (12) Å | θ = 2.4–24.2° |
b = 9.7918 (12) Å | µ = 0.08 mm−1 |
c = 15.996 (2) Å | T = 298 K |
β = 97.254 (2)° | Block, colorless |
V = 1462.4 (3) Å3 | 0.29 × 0.18 × 0.17 mm |
Z = 4 |
Bruker APEX area-detector diffractometer | 2735 independent reflections |
Radiation source: fine-focus sealed tube | 2523 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.030 |
φ and ω scans | θmax = 25.0°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −11→11 |
Tmin = 0.976, Tmax = 0.979 | k = 0→11 |
7716 measured reflections | l = 0→19 |
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)] = 0.076 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.134 | H-atom parameters constrained |
S = 1.35 | w = 1/[σ2(Fo2) + (0.0329P)2 + 0.5185P] where P = (Fo2 + 2Fc2)/3 |
2735 reflections | (Δ/σ)max = 0.001 |
395 parameters | Δρmax = 0.19 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 | Occ. (<1) | |
O1 | 0.6851 (4) | 0.3867 (4) | 0.3830 (2) | 0.0586 (10) | |
O2 | 0.5656 (6) | 0.5758 (5) | 0.3419 (4) | 0.0980 (17) | |
C1 | 0.7524 (5) | 0.2724 (5) | 0.3452 (3) | 0.0450 (12) | |
C2 | 0.6226 (7) | 0.4727 (6) | 0.3226 (5) | 0.0624 (17) | |
N1A | 0.657 (3) | 0.412 (3) | 0.2315 (15) | 0.045 (3) | 0.405 (18) |
C3A | 0.764 (6) | 0.315 (9) | 0.247 (5) | 0.045 (6) | 0.405 (18) |
H3AA | 0.7299 | 0.2353 | 0.2136 | 0.054* | 0.405 (18) |
C4A | 0.887 (4) | 0.350 (3) | 0.219 (2) | 0.060 (3) | 0.405 (18) |
H4AA | 0.9347 | 0.2719 | 0.1984 | 0.072* | 0.405 (18) |
H4AB | 0.9511 | 0.3963 | 0.2622 | 0.072* | 0.405 (18) |
C5A | 0.827 (5) | 0.450 (4) | 0.146 (3) | 0.074 (6) | 0.405 (18) |
H5AA | 0.8949 | 0.5231 | 0.1409 | 0.089* | 0.405 (18) |
H5AB | 0.8129 | 0.4009 | 0.0927 | 0.089* | 0.405 (18) |
C6A | 0.690 (4) | 0.507 (5) | 0.164 (3) | 0.077 (5) | 0.405 (18) |
H6AA | 0.6181 | 0.5035 | 0.1153 | 0.092* | 0.405 (18) |
H6AB | 0.7011 | 0.6002 | 0.1844 | 0.092* | 0.405 (18) |
N1B | 0.628 (2) | 0.4298 (17) | 0.2549 (9) | 0.045 (3) | 0.595 (18) |
C3B | 0.727 (4) | 0.313 (6) | 0.254 (3) | 0.045 (6) | 0.595 (18) |
H3BA | 0.6865 | 0.2391 | 0.2171 | 0.054* | 0.595 (18) |
C4B | 0.855 (2) | 0.3964 (19) | 0.2138 (14) | 0.060 (3) | 0.595 (18) |
H4BA | 0.9112 | 0.4509 | 0.2566 | 0.072* | 0.595 (18) |
H4BB | 0.9183 | 0.3337 | 0.1895 | 0.072* | 0.595 (18) |
C5B | 0.776 (3) | 0.485 (2) | 0.1479 (19) | 0.074 (6) | 0.595 (18) |
H5BA | 0.7583 | 0.4362 | 0.0947 | 0.089* | 0.595 (18) |
H5BB | 0.8306 | 0.5667 | 0.1396 | 0.089* | 0.595 (18) |
C6B | 0.637 (3) | 0.519 (3) | 0.1812 (15) | 0.077 (5) | 0.595 (18) |
H6BA | 0.6365 | 0.6146 | 0.1979 | 0.092* | 0.595 (18) |
H6BB | 0.5565 | 0.5033 | 0.1383 | 0.092* | 0.595 (18) |
C7 | 0.9058 (5) | 0.2631 (5) | 0.3884 (3) | 0.0416 (11) | |
C8 | 0.9686 (6) | 0.3670 (6) | 0.4382 (3) | 0.0574 (14) | |
H8A | 0.9158 | 0.4449 | 0.4467 | 0.069* | |
C9 | 1.1101 (7) | 0.3572 (8) | 0.4761 (4) | 0.0709 (18) | |
H9A | 1.1503 | 0.4282 | 0.5099 | 0.085* | |
C10 | 1.1902 (6) | 0.2436 (8) | 0.4639 (4) | 0.0739 (19) | |
H10A | 1.2847 | 0.2370 | 0.4889 | 0.089* | |
C11 | 1.1296 (6) | 0.1411 (8) | 0.4149 (4) | 0.0751 (19) | |
H11A | 1.1826 | 0.0633 | 0.4063 | 0.090* | |
C12 | 0.9893 (6) | 0.1515 (6) | 0.3775 (4) | 0.0640 (16) | |
H12A | 0.9502 | 0.0801 | 0.3437 | 0.077* | |
C13 | 0.6679 (5) | 0.1438 (5) | 0.3594 (3) | 0.0405 (12) | |
C14 | 0.5932 (5) | 0.1341 (6) | 0.4278 (3) | 0.0556 (14) | |
H14A | 0.5912 | 0.2086 | 0.4636 | 0.067* | |
C15 | 0.5209 (6) | 0.0155 (8) | 0.4445 (4) | 0.0642 (17) | |
H15A | 0.4688 | 0.0114 | 0.4900 | 0.077* | |
C16 | 0.5275 (6) | −0.0951 (7) | 0.3929 (4) | 0.0594 (16) | |
H16A | 0.4804 | −0.1753 | 0.4042 | 0.071* | |
C17 | 0.6018 (6) | −0.0896 (6) | 0.3257 (4) | 0.0564 (15) | |
H17A | 0.6063 | −0.1655 | 0.2912 | 0.068* | |
C18 | 0.6707 (5) | 0.0300 (5) | 0.3090 (3) | 0.0464 (13) | |
H18A | 0.7205 | 0.0338 | 0.2624 | 0.056* | |
O3 | 0.0338 (3) | 0.8839 (4) | 0.1176 (2) | 0.0512 (9) | |
O4 | −0.1716 (4) | 0.8433 (5) | 0.1706 (3) | 0.0818 (14) | |
N2 | 0.0453 (5) | 0.8547 (5) | 0.2563 (3) | 0.0556 (12) | |
C19 | 0.1842 (5) | 0.9028 (5) | 0.1500 (3) | 0.0408 (11) | |
C20 | −0.0435 (6) | 0.8588 (6) | 0.1819 (4) | 0.0577 (15) | |
C21 | 0.1923 (6) | 0.8404 (6) | 0.2382 (3) | 0.0500 (14) | |
H21A | 0.2563 | 0.8950 | 0.2782 | 0.060* | |
C22 | 0.2233 (7) | 0.6896 (7) | 0.2530 (4) | 0.0642 (16) | |
H22A | 0.3254 | 0.6718 | 0.2641 | 0.077* | |
H22B | 0.1821 | 0.6345 | 0.2056 | 0.077* | |
C23 | 0.1487 (7) | 0.6647 (8) | 0.3309 (4) | 0.083 (2) | |
H24A | 0.1210 | 0.5696 | 0.3341 | 0.100* | |
H24B | 0.2117 | 0.6879 | 0.3817 | 0.100* | |
C24 | 0.0180 (8) | 0.7556 (8) | 0.3213 (4) | 0.084 (2) | |
H23A | −0.0680 | 0.7032 | 0.3036 | 0.101* | |
H23B | 0.0073 | 0.8013 | 0.3740 | 0.101* | |
C25 | 0.2115 (5) | 1.0568 (5) | 0.1486 (3) | 0.0406 (12) | |
C26 | 0.2874 (6) | 1.1276 (6) | 0.2135 (4) | 0.0639 (16) | |
H26A | 0.3249 | 1.0819 | 0.2623 | 0.077* | |
C27 | 0.3083 (7) | 1.2675 (7) | 0.2066 (4) | 0.0782 (19) | |
H27A | 0.3590 | 1.3148 | 0.2512 | 0.094* | |
C28 | 0.2555 (7) | 1.3364 (7) | 0.1351 (5) | 0.0709 (18) | |
H28A | 0.2703 | 1.4299 | 0.1308 | 0.085* | |
C29 | 0.1811 (6) | 1.2668 (7) | 0.0704 (4) | 0.0659 (16) | |
H29A | 0.1438 | 1.3129 | 0.0217 | 0.079* | |
C30 | 0.1604 (6) | 1.1276 (6) | 0.0766 (3) | 0.0569 (15) | |
H30A | 0.1110 | 1.0809 | 0.0313 | 0.068* | |
C31 | 0.2734 (5) | 0.8263 (5) | 0.0923 (3) | 0.0418 (12) | |
C32 | 0.4186 (5) | 0.8545 (6) | 0.0963 (3) | 0.0484 (13) | |
H32A | 0.4597 | 0.9209 | 0.1333 | 0.058* | |
C33 | 0.5018 (6) | 0.7853 (7) | 0.0460 (4) | 0.0662 (17) | |
H33A | 0.5989 | 0.8055 | 0.0494 | 0.079* | |
C34 | 0.4448 (7) | 0.6873 (7) | −0.0090 (4) | 0.0726 (19) | |
H34A | 0.5019 | 0.6421 | −0.0435 | 0.087* | |
C35 | 0.3019 (7) | 0.6566 (6) | −0.0126 (4) | 0.0693 (17) | |
H35A | 0.2621 | 0.5892 | −0.0493 | 0.083* | |
C36 | 0.2167 (6) | 0.7252 (6) | 0.0380 (3) | 0.0538 (14) | |
H36A | 0.1202 | 0.7029 | 0.0353 | 0.065* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.080 (3) | 0.035 (2) | 0.060 (2) | 0.0143 (19) | 0.007 (2) | −0.0042 (19) |
O2 | 0.113 (4) | 0.050 (3) | 0.129 (5) | 0.031 (3) | 0.007 (3) | 0.008 (3) |
C1 | 0.060 (3) | 0.034 (3) | 0.040 (3) | 0.002 (3) | 0.004 (2) | −0.004 (2) |
C2 | 0.063 (4) | 0.034 (3) | 0.089 (5) | 0.001 (3) | 0.003 (4) | 0.010 (4) |
N1A | 0.070 (9) | 0.045 (6) | 0.024 (9) | 0.017 (5) | 0.016 (5) | −0.007 (6) |
C3A | 0.050 (18) | 0.038 (3) | 0.046 (8) | −0.010 (14) | 0.007 (12) | −0.001 (4) |
C4A | 0.075 (10) | 0.052 (12) | 0.054 (5) | 0.028 (7) | 0.018 (6) | 0.030 (9) |
C5A | 0.13 (2) | 0.034 (13) | 0.067 (5) | −0.001 (10) | 0.031 (12) | −0.008 (9) |
C6A | 0.108 (19) | 0.067 (7) | 0.057 (11) | 0.014 (11) | 0.018 (9) | 0.022 (8) |
N1B | 0.070 (9) | 0.045 (6) | 0.024 (9) | 0.017 (5) | 0.016 (5) | −0.007 (6) |
C3B | 0.050 (18) | 0.038 (3) | 0.046 (8) | −0.010 (14) | 0.007 (12) | −0.001 (4) |
C4B | 0.075 (10) | 0.052 (12) | 0.054 (5) | 0.028 (7) | 0.018 (6) | 0.030 (9) |
C5B | 0.13 (2) | 0.034 (13) | 0.067 (5) | −0.001 (10) | 0.031 (12) | −0.008 (9) |
C6B | 0.108 (19) | 0.067 (7) | 0.057 (11) | 0.014 (11) | 0.018 (9) | 0.022 (8) |
C7 | 0.058 (3) | 0.036 (3) | 0.031 (3) | −0.006 (3) | 0.007 (2) | −0.002 (2) |
C8 | 0.074 (4) | 0.046 (3) | 0.054 (3) | −0.010 (3) | 0.014 (3) | −0.006 (3) |
C9 | 0.070 (4) | 0.075 (5) | 0.065 (4) | −0.024 (4) | −0.001 (3) | −0.016 (4) |
C10 | 0.054 (4) | 0.094 (6) | 0.071 (4) | −0.011 (4) | −0.003 (3) | −0.003 (4) |
C11 | 0.053 (4) | 0.076 (5) | 0.094 (5) | 0.000 (4) | 0.002 (3) | −0.017 (4) |
C12 | 0.058 (3) | 0.055 (4) | 0.076 (4) | −0.004 (3) | −0.002 (3) | −0.019 (3) |
C13 | 0.036 (3) | 0.042 (3) | 0.043 (3) | 0.006 (2) | 0.000 (2) | 0.006 (2) |
C14 | 0.047 (3) | 0.061 (4) | 0.059 (4) | 0.009 (3) | 0.009 (3) | 0.002 (3) |
C15 | 0.042 (3) | 0.096 (5) | 0.057 (4) | 0.003 (3) | 0.013 (3) | 0.023 (4) |
C16 | 0.046 (3) | 0.059 (4) | 0.069 (4) | −0.012 (3) | −0.009 (3) | 0.020 (3) |
C17 | 0.056 (3) | 0.044 (3) | 0.065 (4) | −0.003 (3) | −0.006 (3) | 0.006 (3) |
C18 | 0.047 (3) | 0.041 (3) | 0.052 (3) | 0.000 (2) | 0.009 (2) | 0.002 (3) |
O3 | 0.0408 (19) | 0.063 (2) | 0.049 (2) | −0.0023 (18) | 0.0037 (16) | −0.0056 (19) |
O4 | 0.048 (2) | 0.096 (4) | 0.105 (4) | −0.007 (2) | 0.021 (2) | −0.020 (3) |
N2 | 0.070 (3) | 0.052 (3) | 0.049 (3) | −0.016 (2) | 0.023 (2) | −0.009 (2) |
C19 | 0.042 (3) | 0.042 (3) | 0.038 (3) | −0.003 (2) | −0.001 (2) | −0.002 (2) |
C20 | 0.056 (4) | 0.049 (4) | 0.068 (4) | −0.004 (3) | 0.011 (3) | −0.025 (3) |
C21 | 0.054 (3) | 0.050 (3) | 0.044 (3) | −0.018 (3) | −0.002 (2) | −0.003 (3) |
C22 | 0.069 (4) | 0.059 (4) | 0.064 (4) | −0.003 (3) | 0.005 (3) | 0.018 (3) |
C23 | 0.103 (5) | 0.075 (5) | 0.067 (4) | −0.032 (4) | −0.003 (4) | 0.018 (4) |
C24 | 0.111 (5) | 0.088 (5) | 0.060 (4) | −0.022 (5) | 0.034 (4) | 0.001 (4) |
C25 | 0.034 (3) | 0.046 (3) | 0.043 (3) | 0.007 (2) | 0.009 (2) | −0.002 (2) |
C26 | 0.073 (4) | 0.049 (4) | 0.066 (4) | −0.013 (3) | −0.010 (3) | 0.003 (3) |
C27 | 0.090 (5) | 0.059 (4) | 0.080 (5) | −0.021 (4) | −0.008 (4) | −0.009 (4) |
C28 | 0.081 (4) | 0.046 (4) | 0.089 (5) | −0.002 (3) | 0.024 (4) | 0.008 (4) |
C29 | 0.072 (4) | 0.054 (4) | 0.073 (4) | 0.019 (3) | 0.013 (3) | 0.018 (3) |
C30 | 0.069 (4) | 0.053 (4) | 0.048 (3) | 0.004 (3) | 0.002 (3) | 0.000 (3) |
C31 | 0.054 (3) | 0.031 (3) | 0.038 (3) | −0.003 (2) | −0.002 (2) | 0.011 (2) |
C32 | 0.049 (3) | 0.044 (3) | 0.053 (3) | −0.001 (3) | 0.009 (2) | 0.005 (3) |
C33 | 0.060 (4) | 0.065 (4) | 0.078 (4) | 0.000 (3) | 0.023 (3) | 0.010 (4) |
C34 | 0.087 (5) | 0.063 (4) | 0.074 (4) | 0.021 (4) | 0.032 (4) | 0.004 (4) |
C35 | 0.096 (5) | 0.050 (4) | 0.062 (4) | −0.003 (4) | 0.011 (3) | −0.008 (3) |
C36 | 0.056 (3) | 0.050 (4) | 0.057 (3) | −0.005 (3) | 0.011 (3) | −0.003 (3) |
O1—C2 | 1.359 (7) | C15—C16 | 1.367 (9) |
O1—C1 | 1.456 (6) | C15—H15A | 0.9300 |
O2—C2 | 1.202 (8) | C16—C17 | 1.355 (8) |
C1—C3B | 1.51 (5) | C16—H16A | 0.9300 |
C1—C13 | 1.522 (7) | C17—C18 | 1.381 (7) |
C1—C7 | 1.523 (7) | C17—H17A | 0.9300 |
C1—C3A | 1.64 (8) | C18—H18A | 0.9300 |
C2—N1B | 1.168 (16) | O3—C20 | 1.355 (6) |
C2—N1A | 1.643 (18) | O3—C19 | 1.457 (5) |
N1A—C3A | 1.39 (8) | O4—C20 | 1.206 (6) |
N1A—C6A | 1.49 (5) | N2—C20 | 1.367 (7) |
C3A—C4A | 1.33 (6) | N2—C21 | 1.456 (6) |
C3A—H3AA | 0.9800 | N2—C24 | 1.468 (8) |
C4A—C5A | 1.58 (5) | C19—C31 | 1.521 (7) |
C4A—H4AA | 0.9700 | C19—C25 | 1.531 (7) |
C4A—H4AB | 0.9700 | C19—C21 | 1.531 (7) |
C5A—C6A | 1.46 (4) | C21—C22 | 1.518 (8) |
C5A—H5AA | 0.9700 | C21—H21A | 0.9800 |
C5A—H5AB | 0.9700 | C22—C23 | 1.526 (8) |
C6A—H6AA | 0.9700 | C22—H22A | 0.9700 |
C6A—H6AB | 0.9700 | C22—H22B | 0.9700 |
N1B—C3B | 1.47 (5) | C23—C24 | 1.511 (9) |
N1B—C6B | 1.48 (3) | C23—H24A | 0.9700 |
C3B—C4B | 1.65 (4) | C23—H24B | 0.9700 |
C3B—H3BA | 0.9800 | C24—H23A | 0.9700 |
C4B—C5B | 1.49 (3) | C24—H23B | 0.9700 |
C4B—H4BA | 0.9700 | C25—C26 | 1.371 (7) |
C4B—H4BB | 0.9700 | C25—C30 | 1.378 (7) |
C5B—C6B | 1.52 (2) | C26—C27 | 1.390 (9) |
C5B—H5BA | 0.9700 | C26—H26A | 0.9300 |
C5B—H5BB | 0.9700 | C27—C28 | 1.366 (9) |
C6B—H6BA | 0.9700 | C27—H27A | 0.9300 |
C6B—H6BB | 0.9700 | C28—C29 | 1.358 (9) |
C7—C12 | 1.370 (7) | C28—H28A | 0.9300 |
C7—C8 | 1.378 (7) | C29—C30 | 1.382 (8) |
C8—C9 | 1.394 (8) | C29—H29A | 0.9300 |
C8—H8A | 0.9300 | C30—H30A | 0.9300 |
C9—C10 | 1.372 (9) | C31—C36 | 1.380 (7) |
C9—H9A | 0.9300 | C31—C32 | 1.387 (7) |
C10—C11 | 1.355 (9) | C32—C33 | 1.371 (7) |
C10—H10A | 0.9300 | C32—H32A | 0.9300 |
C11—C12 | 1.383 (8) | C33—C34 | 1.365 (8) |
C11—H11A | 0.9300 | C33—H33A | 0.9300 |
C12—H12A | 0.9300 | C34—C35 | 1.372 (8) |
C13—C14 | 1.376 (7) | C34—H34A | 0.9300 |
C13—C18 | 1.377 (7) | C35—C36 | 1.383 (8) |
C14—C15 | 1.389 (9) | C35—H35A | 0.9300 |
C14—H14A | 0.9300 | C36—H36A | 0.9300 |
C2—O1—C1 | 110.6 (5) | C18—C13—C1 | 122.2 (4) |
O1—C1—C3B | 100.1 (19) | C13—C14—C15 | 121.5 (6) |
O1—C1—C13 | 108.1 (4) | C13—C14—H14A | 119.3 |
C3B—C1—C13 | 110.1 (18) | C15—C14—H14A | 119.3 |
O1—C1—C7 | 107.1 (4) | C16—C15—C14 | 119.1 (5) |
C3B—C1—C7 | 118.8 (12) | C16—C15—H15A | 120.5 |
C13—C1—C7 | 111.5 (4) | C14—C15—H15A | 120.5 |
O1—C1—C3A | 107 (3) | C17—C16—C15 | 120.9 (6) |
C13—C1—C3A | 117 (3) | C17—C16—H16A | 119.6 |
C7—C1—C3A | 106 (2) | C15—C16—H16A | 119.6 |
N1B—C2—O2 | 127.8 (10) | C16—C17—C18 | 119.4 (6) |
N1B—C2—O1 | 111.8 (9) | C16—C17—H17A | 120.3 |
O2—C2—O1 | 120.3 (7) | C18—C17—H17A | 120.3 |
O2—C2—N1A | 132.5 (12) | C13—C18—C17 | 121.8 (5) |
O1—C2—N1A | 106.9 (11) | C13—C18—H18A | 119.1 |
C3A—N1A—C6A | 110 (3) | C17—C18—H18A | 119.1 |
C3A—N1A—C2 | 108 (4) | C20—O3—C19 | 110.1 (4) |
C6A—N1A—C2 | 120 (2) | C20—N2—C21 | 108.7 (4) |
N1A—C3A—C4A | 114 (6) | C20—N2—C24 | 119.7 (5) |
N1A—C3A—C1 | 102 (4) | C21—N2—C24 | 109.5 (5) |
C4A—C3A—C1 | 124 (5) | O3—C19—C31 | 107.9 (4) |
N1A—C3A—H3AA | 105.3 | O3—C19—C25 | 106.1 (4) |
C4A—C3A—H3AA | 105.2 | C31—C19—C25 | 111.7 (4) |
C1—C3A—H3AA | 105.2 | O3—C19—C21 | 102.2 (4) |
C3A—C4A—C5A | 100 (5) | C31—C19—C21 | 113.3 (4) |
C3A—C4A—H4AA | 112.1 | C25—C19—C21 | 114.6 (4) |
C5A—C4A—H4AA | 111.9 | O4—C20—O3 | 122.2 (6) |
C3A—C4A—H4AB | 111.8 | O4—C20—N2 | 128.0 (6) |
C5A—C4A—H4AB | 111.7 | O3—C20—N2 | 109.8 (4) |
H4AA—C4A—H4AB | 109.5 | N2—C21—C22 | 103.4 (4) |
C6A—C5A—C4A | 109 (4) | N2—C21—C19 | 102.0 (4) |
C6A—C5A—H5AA | 109.9 | C22—C21—C19 | 121.2 (5) |
C4A—C5A—H5AA | 110.0 | N2—C21—H21A | 109.8 |
C6A—C5A—H5AB | 109.8 | C22—C21—H21A | 109.8 |
C4A—C5A—H5AB | 109.8 | C19—C21—H21A | 109.8 |
H5AA—C5A—H5AB | 108.3 | C21—C22—C23 | 100.5 (5) |
C5A—C6A—N1A | 100 (4) | C21—C22—H22A | 111.7 |
C5A—C6A—H6AA | 111.7 | C23—C22—H22A | 111.7 |
N1A—C6A—H6AA | 111.7 | C21—C22—H22B | 111.7 |
C5A—C6A—H6AB | 111.7 | C23—C22—H22B | 111.7 |
N1A—C6A—H6AB | 111.7 | H22A—C22—H22B | 109.4 |
H6AA—C6A—H6AB | 109.5 | C24—C23—C22 | 106.0 (5) |
C2—N1B—C3B | 113 (2) | C24—C23—H24A | 110.5 |
C2—N1B—C6B | 122.6 (16) | C22—C23—H24A | 110.5 |
C3B—N1B—C6B | 110 (2) | C24—C23—H24B | 110.5 |
N1B—C3B—C1 | 102 (3) | C22—C23—H24B | 110.5 |
N1B—C3B—C4B | 97 (3) | H24A—C23—H24B | 108.7 |
C1—C3B—C4B | 118 (3) | N2—C24—C23 | 104.4 (5) |
N1B—C3B—H3BA | 112.5 | N2—C24—H23A | 110.9 |
C1—C3B—H3BA | 112.6 | C23—C24—H23A | 110.9 |
C4B—C3B—H3BA | 112.6 | N2—C24—H23B | 110.9 |
C5B—C4B—C3B | 104 (2) | C23—C24—H23B | 110.9 |
C5B—C4B—H4BA | 111.1 | H23A—C24—H23B | 108.9 |
C3B—C4B—H4BA | 111.0 | C26—C25—C30 | 118.2 (5) |
C5B—C4B—H4BB | 111.0 | C26—C25—C19 | 124.0 (5) |
C3B—C4B—H4BB | 110.9 | C30—C25—C19 | 117.8 (5) |
H4BA—C4B—H4BB | 109.0 | C25—C26—C27 | 120.2 (6) |
C4B—C5B—C6B | 105 (2) | C25—C26—H26A | 119.9 |
C4B—C5B—H5BA | 110.8 | C27—C26—H26A | 119.9 |
C6B—C5B—H5BA | 110.8 | C28—C27—C26 | 120.9 (6) |
C4B—C5B—H5BB | 110.7 | C28—C27—H27A | 119.6 |
C6B—C5B—H5BB | 110.8 | C26—C27—H27A | 119.6 |
H5BA—C5B—H5BB | 108.9 | C29—C28—C27 | 119.2 (6) |
N1B—C6B—C5B | 107 (2) | C29—C28—H28A | 120.4 |
N1B—C6B—H6BA | 110.4 | C27—C28—H28A | 120.4 |
C5B—C6B—H6BA | 110.4 | C28—C29—C30 | 120.3 (6) |
N1B—C6B—H6BB | 110.4 | C28—C29—H29A | 119.8 |
C5B—C6B—H6BB | 110.4 | C30—C29—H29A | 119.8 |
H6BA—C6B—H6BB | 108.6 | C25—C30—C29 | 121.2 (6) |
C12—C7—C8 | 116.8 (5) | C25—C30—H30A | 119.4 |
C12—C7—C1 | 121.0 (5) | C29—C30—H30A | 119.4 |
C8—C7—C1 | 122.1 (5) | C36—C31—C32 | 118.2 (5) |
C7—C8—C9 | 121.2 (6) | C36—C31—C19 | 122.4 (4) |
C7—C8—H8A | 119.4 | C32—C31—C19 | 119.3 (4) |
C9—C8—H8A | 119.4 | C33—C32—C31 | 120.4 (5) |
C10—C9—C8 | 120.3 (6) | C33—C32—H32A | 119.8 |
C10—C9—H9A | 119.8 | C31—C32—H32A | 119.8 |
C8—C9—H9A | 119.8 | C34—C33—C32 | 121.3 (6) |
C11—C10—C9 | 119.0 (6) | C34—C33—H33A | 119.4 |
C11—C10—H10A | 120.5 | C32—C33—H33A | 119.4 |
C9—C10—H10A | 120.5 | C33—C34—C35 | 119.0 (6) |
C10—C11—C12 | 120.4 (6) | C33—C34—H34A | 120.5 |
C10—C11—H11A | 119.8 | C35—C34—H34A | 120.5 |
C12—C11—H11A | 119.8 | C34—C35—C36 | 120.4 (6) |
C7—C12—C11 | 122.3 (6) | C34—C35—H35A | 119.8 |
C7—C12—H12A | 118.8 | C36—C35—H35A | 119.8 |
C11—C12—H12A | 118.8 | C31—C36—C35 | 120.7 (5) |
C14—C13—C18 | 117.3 (5) | C31—C36—H36A | 119.7 |
C14—C13—C1 | 120.3 (5) | C35—C36—H36A | 119.7 |
C2—O1—C1—C3B | 3.9 (15) | C3A—C1—C13—C14 | −148 (3) |
C2—O1—C1—C13 | −111.2 (5) | O1—C1—C13—C18 | 157.2 (4) |
C2—O1—C1—C7 | 128.5 (5) | C3B—C1—C13—C18 | 48.8 (17) |
C2—O1—C1—C3A | 15 (2) | C7—C1—C13—C18 | −85.2 (6) |
C1—O1—C2—N1B | 5.4 (12) | C3A—C1—C13—C18 | 37 (3) |
C1—O1—C2—O2 | −177.5 (6) | C18—C13—C14—C15 | −1.4 (7) |
C1—O1—C2—N1A | −2.3 (13) | C1—C13—C14—C15 | −176.8 (4) |
O2—C2—N1A—C3A | 160 (3) | C13—C14—C15—C16 | 1.8 (8) |
O1—C2—N1A—C3A | −14 (4) | C14—C15—C16—C17 | −0.8 (8) |
O2—C2—N1A—C6A | 33 (4) | C15—C16—C17—C18 | −0.4 (8) |
O1—C2—N1A—C6A | −141 (3) | C14—C13—C18—C17 | 0.1 (7) |
C6A—N1A—C3A—C4A | 18 (7) | C1—C13—C18—C17 | 175.4 (5) |
C2—N1A—C3A—C4A | −114 (5) | C16—C17—C18—C13 | 0.9 (8) |
C6A—N1A—C3A—C1 | 154 (3) | C20—O3—C19—C31 | 137.3 (4) |
C2—N1A—C3A—C1 | 22 (5) | C20—O3—C19—C25 | −102.8 (5) |
O1—C1—C3A—N1A | −24 (5) | C20—O3—C19—C21 | 17.6 (5) |
C13—C1—C3A—N1A | 98 (4) | C19—O3—C20—O4 | 178.0 (5) |
C7—C1—C3A—N1A | −138 (3) | C19—O3—C20—N2 | −2.1 (6) |
O1—C1—C3A—C4A | 106 (6) | C21—N2—C20—O4 | 164.2 (6) |
C13—C1—C3A—C4A | −133 (6) | C24—N2—C20—O4 | 37.5 (9) |
C7—C1—C3A—C4A | −8 (7) | C21—N2—C20—O3 | −15.7 (6) |
N1A—C3A—C4A—C5A | −26 (7) | C24—N2—C20—O3 | −142.4 (5) |
C1—C3A—C4A—C5A | −151 (6) | C20—N2—C21—C22 | −100.9 (5) |
C3A—C4A—C5A—C6A | 25 (6) | C24—N2—C21—C22 | 31.5 (6) |
C4A—C5A—C6A—N1A | −15 (5) | C20—N2—C21—C19 | 25.5 (5) |
C3A—N1A—C6A—C5A | 0 (6) | C24—N2—C21—C19 | 157.9 (5) |
C2—N1A—C6A—C5A | 126 (3) | O3—C19—C21—N2 | −25.1 (5) |
O2—C2—N1B—C3B | 170.2 (18) | C31—C19—C21—N2 | −140.9 (4) |
O1—C2—N1B—C3B | −13 (2) | C25—C19—C21—N2 | 89.2 (5) |
O2—C2—N1B—C6B | 34 (2) | O3—C19—C21—C22 | 88.8 (6) |
O1—C2—N1B—C6B | −149.0 (16) | C31—C19—C21—C22 | −27.1 (7) |
C2—N1B—C3B—C1 | 15 (3) | C25—C19—C21—C22 | −157.0 (5) |
C6B—N1B—C3B—C1 | 156 (2) | N2—C21—C22—C23 | −39.6 (5) |
C2—N1B—C3B—C4B | −106 (2) | C19—C21—C22—C23 | −152.7 (5) |
C6B—N1B—C3B—C4B | 35 (3) | C21—C22—C23—C24 | 34.6 (6) |
O1—C1—C3B—N1B | −10 (2) | C20—N2—C24—C23 | 117.1 (6) |
C13—C1—C3B—N1B | 104 (2) | C21—N2—C24—C23 | −9.3 (6) |
C7—C1—C3B—N1B | −125.8 (16) | C22—C23—C24—N2 | −16.5 (7) |
O1—C1—C3B—C4B | 95 (3) | O3—C19—C25—C26 | 135.5 (5) |
C13—C1—C3B—C4B | −151 (3) | C31—C19—C25—C26 | −107.1 (6) |
C7—C1—C3B—C4B | −21 (4) | C21—C19—C25—C26 | 23.6 (7) |
C3A—C1—C3B—C4B | −27 (19) | O3—C19—C25—C30 | −46.6 (6) |
N1B—C3B—C4B—C5B | −41 (3) | C31—C19—C25—C30 | 70.8 (5) |
C1—C3B—C4B—C5B | −149 (3) | C21—C19—C25—C30 | −158.5 (5) |
C3B—C4B—C5B—C6B | 32 (3) | C30—C25—C26—C27 | 1.4 (9) |
C2—N1B—C6B—C5B | 119 (2) | C19—C25—C26—C27 | 179.3 (6) |
C3B—N1B—C6B—C5B | −18 (3) | C25—C26—C27—C28 | −0.7 (10) |
C4B—C5B—C6B—N1B | −11 (3) | C26—C27—C28—C29 | 0.3 (10) |
O1—C1—C7—C12 | 168.2 (5) | C27—C28—C29—C30 | −0.6 (10) |
C3B—C1—C7—C12 | −80 (2) | C26—C25—C30—C29 | −1.8 (8) |
C13—C1—C7—C12 | 50.1 (6) | C19—C25—C30—C29 | −179.8 (5) |
C3A—C1—C7—C12 | −78 (3) | C28—C29—C30—C25 | 1.4 (9) |
O1—C1—C7—C8 | −13.5 (6) | O3—C19—C31—C36 | −18.4 (6) |
C3B—C1—C7—C8 | 99 (2) | C25—C19—C31—C36 | −134.7 (5) |
C13—C1—C7—C8 | −131.7 (5) | C21—C19—C31—C36 | 93.9 (5) |
C3A—C1—C7—C8 | 100 (3) | O3—C19—C31—C32 | 164.2 (4) |
C12—C7—C8—C9 | −0.7 (8) | C25—C19—C31—C32 | 47.9 (6) |
C1—C7—C8—C9 | −178.9 (5) | C21—C19—C31—C32 | −83.5 (5) |
C7—C8—C9—C10 | 0.5 (9) | C36—C31—C32—C33 | 1.4 (7) |
C8—C9—C10—C11 | −0.3 (10) | C19—C31—C32—C33 | 178.9 (5) |
C9—C10—C11—C12 | 0.3 (10) | C31—C32—C33—C34 | 0.0 (9) |
C8—C7—C12—C11 | 0.7 (9) | C32—C33—C34—C35 | −1.1 (9) |
C1—C7—C12—C11 | 179.0 (5) | C33—C34—C35—C36 | 0.8 (9) |
C10—C11—C12—C7 | −0.5 (10) | C32—C31—C36—C35 | −1.6 (8) |
O1—C1—C13—C14 | −27.5 (6) | C19—C31—C36—C35 | −179.1 (5) |
C3B—C1—C13—C14 | −135.9 (17) | C34—C35—C36—C31 | 0.6 (9) |
C7—C1—C13—C14 | 90.0 (5) |