Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807003741/bv2044sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807003741/bv2044Isup2.hkl |
CCDC reference: 636178
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.
C18H11NO2 | F(000) = 1704 |
Mr = 273.28 | Dx = 1.343 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 2464 reflections |
a = 16.029 (13) Å | θ = 2.5–20.2° |
b = 8.709 (7) Å | µ = 0.09 mm−1 |
c = 29.04 (2) Å | T = 294 K |
V = 4055 (6) Å3 | Plate, colourless |
Z = 12 | 0.26 × 0.24 × 0.12 mm |
Bruker SMART 1000 CCD diffractometer | 3660 independent reflections |
Radiation source: fine-focus sealed tube | 1981 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.087 |
φ and ω scans | θmax = 25.0°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Bruker, 1997) | h = −19→19 |
Tmin = 0.977, Tmax = 0.990 | k = −7→10 |
19648 measured reflections | l = −34→28 |
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)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.185 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0822P)2 + 0.621P] where P = (Fo2 + 2Fc2)/3 |
3660 reflections | (Δ/σ)max = 0.004 |
544 parameters | Δρmax = 0.50 e Å−3 |
7 restraints | Δρmin = −0.22 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 | 0.0721 (4) | 0.6127 (9) | 0.0711 (3) | 0.077 (2) | |
O2 | 0.1807 (4) | 0.2751 (8) | 0.1750 (3) | 0.074 (2) | |
O3 | 0.1951 (3) | 0.2727 (7) | 0.3871 (2) | 0.0655 (18) | |
O4 | 0.0900 (3) | 0.6222 (8) | 0.4902 (2) | 0.0704 (19) | |
O5 | 0.3318 (3) | −0.0368 (6) | 0.3015 (3) | 0.098 (2) | |
O6 | 0.0967 (3) | 0.2553 (5) | 0.2848 (3) | 0.0756 (17) | |
N1 | 0.1482 (4) | 0.4558 (8) | 0.1196 (3) | 0.0555 (19) | |
N2 | 0.1627 (4) | 0.4611 (7) | 0.4407 (2) | 0.0466 (17) | |
N3 | 0.2023 (3) | 0.0764 (6) | 0.2929 (3) | 0.076 (3) | |
C1 | 0.0756 (5) | 0.5064 (12) | 0.0980 (4) | 0.059 (3) | |
C2 | 0.0058 (4) | 0.4085 (9) | 0.1145 (3) | 0.0432 (19) | |
C3 | −0.0778 (5) | 0.4090 (11) | 0.1044 (3) | 0.062 (3) | |
H3 | −0.0993 | 0.4740 | 0.0819 | 0.075* | |
C4 | −0.1291 (6) | 0.3103 (13) | 0.1284 (4) | 0.074 (3) | |
H4 | −0.1858 | 0.3074 | 0.1217 | 0.089* | |
C5 | −0.0981 (6) | 0.2181 (12) | 0.1615 (4) | 0.070 (3) | |
H5 | −0.1345 | 0.1546 | 0.1776 | 0.084* | |
C6 | −0.0138 (5) | 0.2145 (10) | 0.1724 (3) | 0.063 (3) | |
H6 | 0.0068 | 0.1510 | 0.1955 | 0.076* | |
C7 | 0.0385 (5) | 0.3107 (10) | 0.1471 (3) | 0.052 (2) | |
C8 | 0.1303 (5) | 0.3369 (10) | 0.1515 (3) | 0.049 (2) | |
C9 | 0.2286 (5) | 0.5320 (10) | 0.1159 (3) | 0.051 (2) | |
C10 | 0.2572 (5) | 0.6094 (11) | 0.1541 (3) | 0.060 (2) | |
H10 | 0.2264 | 0.6118 | 0.1813 | 0.072* | |
C11 | 0.3350 (6) | 0.6851 (11) | 0.1507 (4) | 0.068 (3) | |
H11 | 0.3560 | 0.7379 | 0.1760 | 0.082* | |
C12 | 0.3795 (6) | 0.6818 (12) | 0.1110 (4) | 0.071 (3) | |
H12 | 0.4305 | 0.7323 | 0.1092 | 0.085* | |
C13 | 0.3487 (4) | 0.6027 (10) | 0.0730 (3) | 0.052 (2) | |
C14 | 0.3936 (6) | 0.6023 (12) | 0.0302 (5) | 0.074 (3) | |
H14 | 0.4423 | 0.6597 | 0.0276 | 0.089* | |
C15 | 0.3657 (6) | 0.5184 (12) | −0.0071 (4) | 0.079 (3) | |
H15 | 0.3962 | 0.5135 | −0.0343 | 0.095* | |
C16 | 0.2920 (6) | 0.4434 (11) | −0.0024 (4) | 0.071 (3) | |
H16 | 0.2720 | 0.3896 | −0.0278 | 0.086* | |
C17 | 0.2448 (5) | 0.4408 (10) | 0.0367 (3) | 0.055 (2) | |
H17 | 0.1955 | 0.3850 | 0.0382 | 0.066* | |
C18 | 0.2726 (4) | 0.5230 (11) | 0.0737 (3) | 0.050 (2) | |
C19 | 0.1435 (5) | 0.3400 (10) | 0.4104 (3) | 0.057 (2) | |
C20 | 0.0523 (4) | 0.3164 (9) | 0.4144 (3) | 0.045 (2) | |
C21 | 0.0012 (5) | 0.2159 (11) | 0.3921 (3) | 0.062 (3) | |
H21 | 0.0222 | 0.1474 | 0.3705 | 0.075* | |
C22 | −0.0836 (5) | 0.2187 (11) | 0.4029 (4) | 0.068 (3) | |
H22 | −0.1199 | 0.1529 | 0.3876 | 0.082* | |
C23 | −0.1147 (5) | 0.3192 (11) | 0.4363 (4) | 0.063 (3) | |
H23 | −0.1714 | 0.3188 | 0.4432 | 0.076* | |
C24 | −0.0620 (5) | 0.4192 (11) | 0.4594 (3) | 0.061 (3) | |
H24 | −0.0819 | 0.4858 | 0.4819 | 0.074* | |
C25 | 0.0227 (4) | 0.4154 (10) | 0.4472 (3) | 0.050 (2) | |
C26 | 0.0909 (5) | 0.5143 (11) | 0.4633 (3) | 0.047 (2) | |
C27 | 0.2440 (4) | 0.5343 (10) | 0.4426 (3) | 0.049 (2) | |
C28 | 0.2735 (5) | 0.6094 (9) | 0.4060 (3) | 0.057 (2) | |
H28 | 0.2414 | 0.6127 | 0.3793 | 0.068* | |
C29 | 0.3516 (5) | 0.6841 (11) | 0.4062 (4) | 0.066 (3) | |
H29 | 0.3715 | 0.7331 | 0.3800 | 0.079* | |
C30 | 0.3975 (5) | 0.6826 (11) | 0.4460 (4) | 0.066 (3) | |
H30 | 0.4489 | 0.7321 | 0.4468 | 0.079* | |
C31 | 0.3680 (4) | 0.6069 (9) | 0.4863 (3) | 0.053 (2) | |
C32 | 0.4138 (5) | 0.5996 (11) | 0.5288 (4) | 0.066 (3) | |
H32 | 0.4652 | 0.6487 | 0.5308 | 0.079* | |
C33 | 0.3854 (6) | 0.5263 (13) | 0.5645 (5) | 0.085 (3) | |
H33 | 0.4166 | 0.5292 | 0.5915 | 0.102* | |
C34 | 0.3079 (6) | 0.4403 (13) | 0.5646 (4) | 0.077 (3) | |
H34 | 0.2900 | 0.3846 | 0.5901 | 0.093* | |
C35 | 0.2634 (5) | 0.4469 (11) | 0.5250 (3) | 0.060 (2) | |
H35 | 0.2128 | 0.3948 | 0.5239 | 0.073* | |
C36 | 0.2894 (4) | 0.5291 (9) | 0.4846 (3) | 0.0399 (19) | |
C37 | 0.2883 (4) | 0.0762 (9) | 0.2912 (5) | 0.100 (5) | |
C38 | 0.3138 (3) | 0.2372 (7) | 0.2855 (4) | 0.0515 (19) | |
C39 | 0.3921 (4) | 0.3026 (8) | 0.2839 (4) | 0.067 (2) | |
H39 | 0.4399 | 0.2421 | 0.2849 | 0.081* | |
C40 | 0.3975 (5) | 0.4586 (8) | 0.2808 (4) | 0.067 (2) | |
H40 | 0.4499 | 0.5044 | 0.2796 | 0.080* | |
C41 | 0.3277 (5) | 0.5495 (8) | 0.2794 (4) | 0.064 (2) | |
H41 | 0.3333 | 0.6558 | 0.2790 | 0.077* | |
C42 | 0.2480 (4) | 0.4837 (7) | 0.2786 (3) | 0.0570 (19) | |
H42 | 0.2002 | 0.5436 | 0.2758 | 0.068* | |
C43 | 0.2435 (4) | 0.3257 (6) | 0.2819 (4) | 0.0470 (17) | |
C44 | 0.1696 (4) | 0.2228 (7) | 0.2851 (4) | 0.060 (2) | |
C45 | 0.1510 (2) | −0.0561 (4) | 0.30707 (17) | 0.060 (2) | |
C46 | 0.1406 (3) | −0.0913 (6) | 0.35339 (15) | 0.069 (3) | |
H46 | 0.1676 | −0.0334 | 0.3758 | 0.083* | |
C47 | 0.0897 (3) | −0.2133 (7) | 0.36628 (15) | 0.068 (3) | |
H47 | 0.0828 | −0.2369 | 0.3973 | 0.082* | |
C48 | 0.0493 (3) | −0.3000 (5) | 0.3329 (2) | 0.083 (3) | |
H48 | 0.0153 | −0.3816 | 0.3415 | 0.100* | |
C49 | 0.05972 (17) | −0.2647 (3) | 0.28653 (18) | 0.0514 (18) | |
C50 | 0.11054 (17) | −0.1427 (3) | 0.27364 (14) | 0.0429 (18) | |
C51 | 0.1210 (3) | −0.1075 (6) | 0.22732 (15) | 0.076 (3) | |
H51 | 0.1550 | −0.0259 | 0.2187 | 0.091* | |
C52 | 0.0805 (4) | −0.1941 (7) | 0.19389 (15) | 0.076 (3) | |
H52 | 0.0875 | −0.1705 | 0.1629 | 0.091* | |
C53 | 0.0297 (3) | −0.3161 (7) | 0.2068 (2) | 0.093 (3) | |
H53 | 0.0027 | −0.3741 | 0.1844 | 0.112* | |
C54 | 0.0193 (2) | −0.3514 (4) | 0.2531 (2) | 0.094 (4) | |
H54 | −0.0147 | −0.4329 | 0.2617 | 0.113* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.049 (4) | 0.095 (5) | 0.088 (5) | 0.003 (3) | 0.004 (3) | 0.037 (5) |
O2 | 0.038 (3) | 0.081 (5) | 0.101 (5) | 0.008 (3) | −0.003 (3) | 0.023 (4) |
O3 | 0.037 (3) | 0.073 (4) | 0.086 (5) | 0.008 (3) | 0.002 (3) | −0.024 (4) |
O4 | 0.056 (4) | 0.074 (4) | 0.081 (5) | −0.006 (3) | 0.013 (3) | −0.026 (4) |
O5 | 0.055 (3) | 0.061 (3) | 0.177 (7) | 0.011 (3) | 0.013 (4) | 0.014 (4) |
O6 | 0.027 (3) | 0.060 (3) | 0.140 (5) | 0.007 (2) | 0.004 (4) | 0.009 (5) |
N1 | 0.036 (4) | 0.064 (5) | 0.067 (5) | −0.005 (3) | −0.002 (3) | 0.016 (4) |
N2 | 0.032 (3) | 0.050 (4) | 0.057 (5) | 0.003 (3) | 0.001 (3) | −0.008 (4) |
N3 | 0.024 (3) | 0.039 (3) | 0.166 (9) | −0.006 (2) | 0.005 (4) | 0.010 (4) |
C1 | 0.042 (5) | 0.060 (6) | 0.076 (7) | 0.004 (4) | −0.006 (5) | 0.001 (6) |
C2 | 0.036 (4) | 0.049 (5) | 0.045 (5) | −0.005 (4) | 0.005 (4) | −0.003 (4) |
C3 | 0.048 (5) | 0.075 (7) | 0.064 (6) | −0.001 (5) | −0.009 (4) | −0.002 (5) |
C4 | 0.041 (5) | 0.084 (8) | 0.096 (8) | −0.017 (5) | 0.000 (6) | −0.011 (7) |
C5 | 0.048 (5) | 0.071 (7) | 0.090 (9) | −0.009 (5) | 0.005 (5) | 0.004 (6) |
C6 | 0.046 (5) | 0.060 (6) | 0.085 (7) | −0.005 (4) | 0.009 (5) | 0.006 (5) |
C7 | 0.036 (4) | 0.054 (5) | 0.066 (6) | −0.004 (4) | 0.007 (4) | −0.006 (5) |
C8 | 0.037 (4) | 0.052 (5) | 0.058 (6) | 0.005 (4) | 0.008 (5) | −0.004 (5) |
C9 | 0.035 (4) | 0.059 (5) | 0.061 (6) | −0.007 (4) | −0.011 (4) | 0.011 (5) |
C10 | 0.052 (5) | 0.076 (7) | 0.051 (6) | −0.002 (4) | 0.002 (5) | −0.011 (5) |
C11 | 0.061 (6) | 0.077 (7) | 0.068 (7) | −0.014 (5) | −0.021 (6) | −0.007 (5) |
C12 | 0.041 (5) | 0.082 (7) | 0.090 (8) | −0.011 (5) | −0.005 (6) | 0.031 (6) |
C13 | 0.028 (4) | 0.052 (5) | 0.075 (6) | −0.001 (4) | −0.008 (5) | 0.002 (5) |
C14 | 0.042 (5) | 0.060 (7) | 0.121 (10) | 0.003 (4) | 0.024 (6) | 0.026 (7) |
C15 | 0.065 (7) | 0.076 (7) | 0.096 (9) | 0.001 (6) | 0.032 (6) | 0.006 (7) |
C16 | 0.065 (6) | 0.071 (7) | 0.078 (8) | 0.007 (5) | 0.010 (6) | −0.020 (6) |
C17 | 0.045 (5) | 0.055 (5) | 0.066 (6) | 0.002 (4) | 0.003 (5) | 0.001 (5) |
C18 | 0.028 (4) | 0.056 (6) | 0.065 (6) | 0.000 (4) | 0.000 (4) | 0.005 (5) |
C19 | 0.035 (4) | 0.057 (6) | 0.077 (7) | 0.000 (4) | −0.007 (5) | −0.005 (5) |
C20 | 0.026 (4) | 0.047 (5) | 0.063 (6) | 0.004 (4) | −0.004 (4) | 0.004 (5) |
C21 | 0.042 (5) | 0.071 (6) | 0.074 (7) | 0.002 (4) | −0.002 (5) | −0.012 (5) |
C22 | 0.038 (5) | 0.071 (7) | 0.096 (8) | −0.014 (4) | −0.008 (5) | −0.002 (6) |
C23 | 0.031 (4) | 0.066 (6) | 0.094 (7) | −0.006 (4) | 0.006 (5) | 0.002 (6) |
C24 | 0.040 (5) | 0.073 (7) | 0.071 (7) | 0.000 (4) | 0.006 (4) | 0.007 (6) |
C25 | 0.023 (4) | 0.059 (5) | 0.067 (6) | 0.003 (4) | −0.004 (4) | 0.013 (5) |
C26 | 0.041 (5) | 0.054 (6) | 0.047 (5) | 0.001 (4) | −0.006 (4) | 0.003 (5) |
C27 | 0.025 (4) | 0.058 (5) | 0.063 (6) | 0.006 (4) | 0.008 (4) | −0.004 (5) |
C28 | 0.041 (5) | 0.059 (6) | 0.070 (7) | −0.007 (4) | 0.014 (5) | −0.013 (5) |
C29 | 0.053 (5) | 0.068 (6) | 0.076 (7) | −0.008 (5) | 0.021 (5) | 0.000 (5) |
C30 | 0.039 (5) | 0.061 (6) | 0.097 (8) | −0.012 (4) | 0.020 (6) | −0.007 (6) |
C31 | 0.031 (4) | 0.051 (5) | 0.078 (7) | 0.000 (4) | −0.005 (5) | −0.024 (5) |
C32 | 0.044 (5) | 0.057 (6) | 0.096 (8) | 0.004 (4) | −0.016 (6) | −0.014 (6) |
C33 | 0.071 (7) | 0.077 (8) | 0.109 (10) | 0.004 (6) | −0.038 (7) | 0.009 (7) |
C34 | 0.065 (6) | 0.093 (8) | 0.074 (7) | 0.003 (5) | −0.020 (6) | −0.012 (6) |
C35 | 0.038 (4) | 0.072 (6) | 0.071 (7) | 0.002 (4) | −0.003 (5) | −0.004 (5) |
C36 | 0.030 (4) | 0.037 (4) | 0.053 (5) | 0.002 (3) | 0.004 (4) | −0.006 (4) |
C37 | 0.024 (4) | 0.045 (4) | 0.229 (15) | 0.010 (3) | 0.010 (6) | 0.013 (7) |
C38 | 0.021 (3) | 0.046 (3) | 0.088 (6) | 0.001 (3) | 0.006 (4) | 0.001 (5) |
C39 | 0.039 (4) | 0.063 (4) | 0.099 (6) | −0.002 (3) | 0.012 (6) | 0.007 (7) |
C40 | 0.052 (5) | 0.063 (5) | 0.085 (6) | −0.023 (4) | 0.016 (6) | −0.006 (7) |
C41 | 0.060 (5) | 0.046 (4) | 0.085 (6) | −0.015 (4) | 0.007 (6) | 0.002 (6) |
C42 | 0.048 (4) | 0.050 (4) | 0.074 (5) | 0.002 (3) | 0.010 (5) | −0.003 (5) |
C43 | 0.036 (4) | 0.034 (3) | 0.071 (5) | −0.006 (3) | 0.008 (5) | −0.016 (5) |
C44 | 0.032 (4) | 0.044 (4) | 0.103 (7) | 0.003 (3) | 0.007 (5) | 0.000 (6) |
C45 | 0.035 (4) | 0.057 (5) | 0.088 (7) | 0.008 (4) | 0.008 (4) | 0.007 (5) |
C46 | 0.070 (6) | 0.050 (5) | 0.087 (8) | 0.006 (5) | 0.021 (5) | 0.018 (5) |
C47 | 0.072 (6) | 0.074 (7) | 0.059 (7) | 0.017 (5) | 0.016 (5) | 0.019 (5) |
C48 | 0.058 (6) | 0.066 (6) | 0.125 (10) | 0.016 (5) | 0.026 (6) | 0.015 (7) |
C49 | 0.033 (4) | 0.040 (4) | 0.081 (6) | 0.003 (3) | 0.003 (5) | −0.002 (5) |
C50 | 0.027 (4) | 0.033 (3) | 0.069 (6) | 0.000 (3) | 0.005 (4) | 0.000 (4) |
C51 | 0.053 (5) | 0.079 (7) | 0.096 (8) | 0.018 (5) | 0.012 (6) | 0.003 (6) |
C52 | 0.090 (8) | 0.070 (7) | 0.067 (7) | −0.003 (6) | −0.014 (6) | −0.012 (6) |
C53 | 0.105 (9) | 0.074 (8) | 0.102 (9) | 0.023 (7) | 0.001 (7) | −0.014 (6) |
C54 | 0.045 (5) | 0.052 (5) | 0.186 (13) | 0.015 (4) | −0.022 (7) | −0.037 (7) |
O1—C1 | 1.213 (11) | C23—H23 | 0.9300 |
O2—C8 | 1.186 (10) | C24—C25 | 1.403 (11) |
O3—C19 | 1.220 (10) | C24—H24 | 0.9300 |
O4—C26 | 1.222 (10) | C25—C26 | 1.468 (11) |
O5—C37 | 1.243 (9) | C27—C28 | 1.335 (11) |
O6—C44 | 1.202 (7) | C27—C36 | 1.422 (11) |
N1—C1 | 1.395 (10) | C28—C29 | 1.411 (11) |
N1—C8 | 1.417 (11) | C28—H28 | 0.9300 |
N1—C9 | 1.454 (10) | C29—C30 | 1.370 (13) |
N2—C26 | 1.403 (10) | C29—H29 | 0.9300 |
N2—C19 | 1.408 (11) | C30—C31 | 1.423 (13) |
N2—C27 | 1.452 (10) | C30—H30 | 0.9300 |
N3—C37 | 1.380 (9) | C31—C36 | 1.431 (10) |
N3—C44 | 1.397 (9) | C31—C32 | 1.437 (14) |
N3—C45 | 1.475 (6) | C32—C33 | 1.299 (14) |
C1—C2 | 1.486 (12) | C32—H32 | 0.9300 |
C2—C3 | 1.372 (11) | C33—C34 | 1.451 (14) |
C2—C7 | 1.376 (11) | C33—H33 | 0.9300 |
C3—C4 | 1.378 (13) | C34—C35 | 1.356 (12) |
C3—H3 | 0.9300 | C34—H34 | 0.9300 |
C4—C5 | 1.346 (14) | C35—C36 | 1.436 (12) |
C4—H4 | 0.9300 | C35—H35 | 0.9300 |
C5—C6 | 1.388 (13) | C37—C38 | 1.471 (10) |
C5—H5 | 0.9300 | C38—C43 | 1.369 (8) |
C6—C7 | 1.395 (12) | C38—C39 | 1.378 (9) |
C6—H6 | 0.9300 | C39—C40 | 1.364 (9) |
C7—C8 | 1.496 (11) | C39—H39 | 0.9300 |
C9—C10 | 1.378 (11) | C40—C41 | 1.372 (10) |
C9—C18 | 1.415 (12) | C40—H40 | 0.9300 |
C10—C11 | 1.415 (12) | C41—C42 | 1.401 (9) |
C10—H10 | 0.9300 | C41—H41 | 0.9300 |
C11—C12 | 1.354 (14) | C42—C43 | 1.381 (8) |
C11—H11 | 0.9300 | C42—H42 | 0.9300 |
C12—C13 | 1.391 (13) | C43—C44 | 1.488 (8) |
C12—H12 | 0.9300 | C45—C46 | 1.3900 |
C13—C18 | 1.404 (11) | C45—C50 | 1.3900 |
C13—C14 | 1.435 (14) | C46—C47 | 1.3900 |
C14—C15 | 1.382 (15) | C46—H46 | 0.9300 |
C14—H14 | 0.9300 | C47—C48 | 1.3900 |
C15—C16 | 1.357 (13) | C47—H47 | 0.9300 |
C15—H15 | 0.9300 | C48—C49 | 1.3900 |
C16—C17 | 1.365 (12) | C48—H48 | 0.9300 |
C16—H16 | 0.9300 | C49—C50 | 1.3900 |
C17—C18 | 1.366 (12) | C49—C54 | 1.3900 |
C17—H17 | 0.9300 | C50—C51 | 1.3900 |
C19—C20 | 1.480 (10) | C51—C52 | 1.3900 |
C20—C21 | 1.362 (11) | C51—H51 | 0.9300 |
C20—C25 | 1.371 (11) | C52—C53 | 1.3900 |
C21—C22 | 1.395 (11) | C52—H52 | 0.9300 |
C21—H21 | 0.9300 | C53—C54 | 1.3900 |
C22—C23 | 1.399 (13) | C53—H53 | 0.9300 |
C22—H22 | 0.9300 | C54—H54 | 0.9300 |
C23—C24 | 1.386 (13) | ||
C1—N1—C8 | 110.9 (7) | N2—C26—C25 | 105.5 (7) |
C1—N1—C9 | 124.2 (7) | C28—C27—C36 | 121.2 (8) |
C8—N1—C9 | 124.2 (7) | C28—C27—N2 | 120.2 (8) |
C26—N2—C19 | 111.1 (7) | C36—C27—N2 | 118.5 (7) |
C26—N2—C27 | 125.0 (7) | C27—C28—C29 | 122.4 (9) |
C19—N2—C27 | 123.3 (6) | C27—C28—H28 | 118.8 |
C37—N3—C44 | 111.7 (6) | C29—C28—H28 | 118.8 |
C37—N3—C45 | 124.5 (6) | C30—C29—C28 | 118.5 (9) |
C44—N3—C45 | 123.4 (5) | C30—C29—H29 | 120.8 |
O1—C1—N1 | 124.7 (8) | C28—C29—H29 | 120.8 |
O1—C1—C2 | 127.7 (8) | C29—C30—C31 | 121.3 (8) |
N1—C1—C2 | 107.5 (8) | C29—C30—H30 | 119.4 |
C3—C2—C7 | 121.4 (7) | C31—C30—H30 | 119.4 |
C3—C2—C1 | 131.6 (8) | C30—C31—C36 | 118.9 (8) |
C7—C2—C1 | 106.9 (7) | C30—C31—C32 | 123.8 (8) |
C2—C3—C4 | 118.1 (9) | C36—C31—C32 | 117.3 (9) |
C2—C3—H3 | 120.9 | C33—C32—C31 | 121.9 (9) |
C4—C3—H3 | 120.9 | C33—C32—H32 | 119.0 |
C5—C4—C3 | 120.9 (9) | C31—C32—H32 | 119.0 |
C5—C4—H4 | 119.6 | C32—C33—C34 | 123.7 (10) |
C3—C4—H4 | 119.6 | C32—C33—H33 | 118.1 |
C4—C5—C6 | 122.3 (10) | C34—C33—H33 | 118.1 |
C4—C5—H5 | 118.8 | C35—C34—C33 | 115.2 (10) |
C6—C5—H5 | 118.8 | C35—C34—H34 | 122.4 |
C5—C6—C7 | 116.8 (9) | C33—C34—H34 | 122.4 |
C5—C6—H6 | 121.6 | C34—C35—C36 | 124.2 (8) |
C7—C6—H6 | 121.6 | C34—C35—H35 | 117.9 |
C2—C7—C6 | 120.3 (7) | C36—C35—H35 | 117.9 |
C2—C7—C8 | 109.9 (7) | C27—C36—C31 | 117.7 (8) |
C6—C7—C8 | 129.6 (9) | C27—C36—C35 | 124.6 (7) |
O2—C8—N1 | 124.7 (7) | C31—C36—C35 | 117.6 (8) |
O2—C8—C7 | 130.6 (8) | O5—C37—N3 | 123.6 (7) |
N1—C8—C7 | 104.7 (7) | O5—C37—C38 | 128.8 (7) |
C10—C9—C18 | 124.0 (8) | N3—C37—C38 | 106.3 (6) |
C10—C9—N1 | 117.2 (8) | C43—C38—C39 | 120.9 (6) |
C18—C9—N1 | 118.8 (7) | C43—C38—C37 | 108.4 (5) |
C9—C10—C11 | 117.6 (9) | C39—C38—C37 | 130.6 (6) |
C9—C10—H10 | 121.2 | C40—C39—C38 | 118.1 (6) |
C11—C10—H10 | 121.2 | C40—C39—H39 | 120.9 |
C12—C11—C10 | 121.0 (9) | C38—C39—H39 | 120.9 |
C12—C11—H11 | 119.5 | C39—C40—C41 | 121.7 (6) |
C10—C11—H11 | 119.5 | C39—C40—H40 | 119.2 |
C11—C12—C13 | 119.9 (8) | C41—C40—H40 | 119.2 |
C11—C12—H12 | 120.0 | C40—C41—C42 | 120.5 (6) |
C13—C12—H12 | 120.0 | C40—C41—H41 | 119.7 |
C12—C13—C18 | 122.7 (9) | C42—C41—H41 | 119.7 |
C12—C13—C14 | 120.7 (9) | C43—C42—C41 | 117.0 (6) |
C18—C13—C14 | 116.5 (9) | C43—C42—H42 | 121.5 |
C15—C14—C13 | 121.2 (9) | C41—C42—H42 | 121.5 |
C15—C14—H14 | 119.4 | C38—C43—C42 | 121.6 (6) |
C13—C14—H14 | 119.4 | C38—C43—C44 | 108.1 (5) |
C16—C15—C14 | 117.3 (10) | C42—C43—C44 | 130.2 (6) |
C16—C15—H15 | 121.4 | O6—C44—N3 | 125.5 (6) |
C14—C15—H15 | 121.4 | O6—C44—C43 | 129.1 (6) |
C15—C16—C17 | 125.0 (10) | N3—C44—C43 | 105.2 (5) |
C15—C16—H16 | 117.5 | C46—C45—C50 | 120.0 |
C17—C16—H16 | 117.5 | C46—C45—N3 | 120.6 (4) |
C16—C17—C18 | 117.8 (8) | C50—C45—N3 | 119.3 (4) |
C16—C17—H17 | 121.1 | C45—C46—C47 | 120.0 |
C18—C17—H17 | 121.1 | C45—C46—H46 | 120.0 |
C17—C18—C13 | 122.1 (9) | C47—C46—H46 | 120.0 |
C17—C18—C9 | 123.2 (7) | C48—C47—C46 | 120.0 |
C13—C18—C9 | 114.7 (8) | C48—C47—H47 | 120.0 |
O3—C19—N2 | 124.0 (7) | C46—C47—H47 | 120.0 |
O3—C19—C20 | 130.3 (8) | C47—C48—C49 | 120.0 |
N2—C19—C20 | 105.7 (7) | C47—C48—H48 | 120.0 |
C21—C20—C25 | 121.8 (7) | C49—C48—H48 | 120.0 |
C21—C20—C19 | 130.2 (8) | C48—C49—C50 | 120.0 |
C25—C20—C19 | 108.0 (7) | C48—C49—C54 | 120.0 |
C20—C21—C22 | 117.9 (9) | C50—C49—C54 | 120.0 |
C20—C21—H21 | 121.1 | C51—C50—C49 | 120.0 |
C22—C21—H21 | 121.1 | C51—C50—C45 | 120.0 |
C21—C22—C23 | 121.0 (8) | C49—C50—C45 | 120.0 |
C21—C22—H22 | 119.5 | C50—C51—C52 | 120.0 |
C23—C22—H22 | 119.5 | C50—C51—H51 | 120.0 |
C24—C23—C22 | 120.7 (8) | C52—C51—H51 | 120.0 |
C24—C23—H23 | 119.6 | C53—C52—C51 | 120.0 |
C22—C23—H23 | 119.6 | C53—C52—H52 | 120.0 |
C23—C24—C25 | 117.0 (9) | C51—C52—H52 | 120.0 |
C23—C24—H24 | 121.5 | C52—C53—C54 | 120.0 |
C25—C24—H24 | 121.5 | C52—C53—H53 | 120.0 |
C20—C25—C24 | 121.6 (8) | C54—C53—H53 | 120.0 |
C20—C25—C26 | 109.5 (7) | C53—C54—C49 | 120.0 |
C24—C25—C26 | 128.8 (9) | C53—C54—H54 | 120.0 |
O4—C26—N2 | 124.2 (7) | C49—C54—H54 | 120.0 |
O4—C26—C25 | 130.3 (8) | ||
C8—N1—C1—O1 | 175.8 (10) | C24—C25—C26—N2 | 179.7 (8) |
C9—N1—C1—O1 | 5.5 (15) | C26—N2—C27—C28 | −107.5 (10) |
C8—N1—C1—C2 | −3.5 (10) | C19—N2—C27—C28 | 62.9 (11) |
C9—N1—C1—C2 | −173.8 (8) | C26—N2—C27—C36 | 70.0 (10) |
O1—C1—C2—C3 | 0.7 (17) | C19—N2—C27—C36 | −119.6 (9) |
N1—C1—C2—C3 | 180.0 (8) | C36—C27—C28—C29 | 1.7 (13) |
O1—C1—C2—C7 | −175.8 (10) | N2—C27—C28—C29 | 179.2 (7) |
N1—C1—C2—C7 | 3.5 (9) | C27—C28—C29—C30 | −1.9 (13) |
C7—C2—C3—C4 | 1.3 (13) | C28—C29—C30—C31 | 0.5 (14) |
C1—C2—C3—C4 | −174.8 (9) | C29—C30—C31—C36 | 0.9 (13) |
C2—C3—C4—C5 | 1.1 (14) | C29—C30—C31—C32 | 179.1 (9) |
C3—C4—C5—C6 | −1.5 (16) | C30—C31—C32—C33 | −178.5 (9) |
C4—C5—C6—C7 | −0.6 (15) | C36—C31—C32—C33 | −0.3 (13) |
C3—C2—C7—C6 | −3.4 (13) | C31—C32—C33—C34 | 2.8 (17) |
C1—C2—C7—C6 | 173.5 (8) | C32—C33—C34—C35 | −3.1 (15) |
C3—C2—C7—C8 | −179.1 (7) | C33—C34—C35—C36 | 1.1 (14) |
C1—C2—C7—C8 | −2.2 (9) | C28—C27—C36—C31 | −0.2 (11) |
C5—C6—C7—C2 | 2.9 (13) | N2—C27—C36—C31 | −177.7 (7) |
C5—C6—C7—C8 | 177.7 (9) | C28—C27—C36—C35 | −177.9 (8) |
C1—N1—C8—O2 | −178.8 (9) | N2—C27—C36—C35 | 4.6 (11) |
C9—N1—C8—O2 | −8.6 (14) | C30—C31—C36—C27 | −1.1 (11) |
C1—N1—C8—C7 | 2.2 (9) | C32—C31—C36—C27 | −179.4 (7) |
C9—N1—C8—C7 | 172.4 (7) | C30—C31—C36—C35 | 176.7 (7) |
C2—C7—C8—O2 | −178.8 (9) | C32—C31—C36—C35 | −1.5 (10) |
C6—C7—C8—O2 | 6.0 (16) | C34—C35—C36—C27 | 178.7 (9) |
C2—C7—C8—N1 | 0.1 (9) | C34—C35—C36—C31 | 1.0 (12) |
C6—C7—C8—N1 | −175.1 (9) | C44—N3—C37—O5 | 172.6 (12) |
C1—N1—C9—C10 | 108.2 (10) | C45—N3—C37—O5 | 0 (2) |
C8—N1—C9—C10 | −60.8 (11) | C44—N3—C37—C38 | 4.8 (15) |
C1—N1—C9—C18 | −71.8 (11) | C45—N3—C37—C38 | −167.9 (9) |
C8—N1—C9—C18 | 119.2 (9) | O5—C37—C38—C43 | −169.6 (14) |
C18—C9—C10—C11 | 0.5 (14) | N3—C37—C38—C43 | −2.7 (15) |
N1—C9—C10—C11 | −179.5 (8) | O5—C37—C38—C39 | 10 (2) |
C9—C10—C11—C12 | 0.3 (14) | N3—C37—C38—C39 | 176.7 (12) |
C10—C11—C12—C13 | −0.2 (14) | C43—C38—C39—C40 | 2.9 (18) |
C11—C12—C13—C18 | −0.6 (14) | C37—C38—C39—C40 | −176.4 (13) |
C11—C12—C13—C14 | 177.8 (9) | C38—C39—C40—C41 | 0 (2) |
C12—C13—C14—C15 | 177.0 (9) | C39—C40—C41—C42 | −3.6 (19) |
C18—C13—C14—C15 | −4.5 (13) | C40—C41—C42—C43 | 3.7 (17) |
C13—C14—C15—C16 | 3.5 (14) | C39—C38—C43—C42 | −2.7 (18) |
C14—C15—C16—C17 | −2.1 (15) | C37—C38—C43—C42 | 176.7 (11) |
C15—C16—C17—C18 | 1.7 (14) | C39—C38—C43—C44 | −179.7 (12) |
C16—C17—C18—C13 | −2.8 (13) | C37—C38—C43—C44 | −0.3 (13) |
C16—C17—C18—C9 | 178.7 (9) | C41—C42—C43—C38 | −0.7 (17) |
C12—C13—C18—C17 | −177.4 (8) | C41—C42—C43—C44 | 175.6 (11) |
C14—C13—C18—C17 | 4.1 (12) | C37—N3—C44—O6 | −179.8 (14) |
C12—C13—C18—C9 | 1.3 (12) | C45—N3—C44—O6 | −7.0 (18) |
C14—C13—C18—C9 | −177.2 (8) | C37—N3—C44—C43 | −4.9 (14) |
C10—C9—C18—C17 | 177.4 (9) | C45—N3—C44—C43 | 167.9 (8) |
N1—C9—C18—C17 | −2.6 (12) | C38—C43—C44—O6 | 177.7 (14) |
C10—C9—C18—C13 | −1.2 (13) | C42—C43—C44—O6 | 1 (2) |
N1—C9—C18—C13 | 178.7 (7) | C38—C43—C44—N3 | 3.1 (12) |
C26—N2—C19—O3 | −179.1 (9) | C42—C43—C44—N3 | −173.6 (11) |
C27—N2—C19—O3 | 9.4 (14) | C37—N3—C45—C46 | 79.1 (11) |
C26—N2—C19—C20 | 0.3 (9) | C44—N3—C45—C46 | −92.7 (9) |
C27—N2—C19—C20 | −171.3 (7) | C37—N3—C45—C50 | −103.0 (11) |
O3—C19—C20—C21 | −1.9 (17) | C44—N3—C45—C50 | 85.1 (10) |
N2—C19—C20—C21 | 178.8 (9) | C50—C45—C46—C47 | 0.0 |
O3—C19—C20—C25 | 176.5 (10) | N3—C45—C46—C47 | 177.8 (4) |
N2—C19—C20—C25 | −2.8 (9) | C45—C46—C47—C48 | 0.0 |
C25—C20—C21—C22 | 1.7 (14) | C46—C47—C48—C49 | 0.0 |
C19—C20—C21—C22 | 179.9 (9) | C47—C48—C49—C50 | 0.0 |
C20—C21—C22—C23 | −1.6 (15) | C47—C48—C49—C54 | 180.0 |
C21—C22—C23—C24 | 0.4 (16) | C48—C49—C50—C51 | 180.0 |
C22—C23—C24—C25 | 0.6 (14) | C54—C49—C50—C51 | 0.0 |
C21—C20—C25—C24 | −0.6 (13) | C48—C49—C50—C45 | 0.0 |
C19—C20—C25—C24 | −179.2 (8) | C54—C49—C50—C45 | 180.0 |
C21—C20—C25—C26 | −177.2 (8) | C46—C45—C50—C51 | 180.0 |
C19—C20—C25—C26 | 4.2 (9) | N3—C45—C50—C51 | 2.2 (4) |
C23—C24—C25—C20 | −0.6 (13) | C46—C45—C50—C49 | 0.0 |
C23—C24—C25—C26 | 175.3 (9) | N3—C45—C50—C49 | −177.8 (4) |
C19—N2—C26—O4 | −177.3 (8) | C49—C50—C51—C52 | 0.0 |
C27—N2—C26—O4 | −5.9 (13) | C45—C50—C51—C52 | 180.0 |
C19—N2—C26—C25 | 2.2 (9) | C50—C51—C52—C53 | 0.0 |
C27—N2—C26—C25 | 173.6 (7) | C51—C52—C53—C54 | 0.0 |
C20—C25—C26—O4 | 175.4 (9) | C52—C53—C54—C49 | 0.0 |
C24—C25—C26—O4 | −0.9 (16) | C48—C49—C54—C53 | 180.0 |
C20—C25—C26—N2 | −4.0 (9) | C50—C49—C54—C53 | 0.0 |