Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801014234/ob6067sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801014234/ob6067Isup2.hkl |
CCDC reference: 162410
Aspergillus ochraceus, an Australian isolate D2306 (Connole et al., 1981), was grown on Sabourauds agar plates (pH 5.9, 298 K, 10–14 d). The mycelial mat was washed with distilled water (4 × 5 ml). The extracts were combined, the volume reduced to ca 50%, filtered, centrifuged, and extracted with CHCl3. Preparative TLC (silica gel) furnished ca 100 mg cycloechinulin per m2 mycelial mat. Cycloechinulin (I) was spectroscopically characterized before recrystallization. Single crystals of (I) were obtained on slow evaporation of MeOH at room temperature.
The large s.u. value of the Flack (1983) parameter, 2.7 (19), indicates that the absolute structure cannot be determined with Mo radiation. The stereostructure of the asymmetric carbon, C114 (C214, C314 or C414) in the Scheme and Figs. 1–8 was just assumed tentatively. The value of (Δ/σ)max is 0.121 (>0.10) and the C119 has ADP max/min ratio 4.20. These results may be due to the rough packing of four independent molecules.
Data collection: CAD-4-PC Software (Enraf-Nonius, 1992); cell refinement: CELLDIM in CAD-4-PC Software; data reduction: XCAD4 (McArdle & Higgins, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication: OSCAIL (McArdle, 1993).
C20H21N3O3·0.25CH4O | F(000) = 1524 |
Mr = 359.41 | Dx = 1.282 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
a = 15.222 (2) Å | Cell parameters from 25 reflections |
b = 16.848 (2) Å | θ = 12–18° |
c = 15.930 (2) Å | µ = 0.09 mm−1 |
β = 114.27 (1)° | T = 298 K |
V = 3724.3 (8) Å3 | Block, colourless |
Z = 8 | 0.6 × 0.3 × 0.3 mm |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.028 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.4° |
Graphite monochromator | h = −18→18 |
ω–2θ scans | k = −19→19 |
14273 measured reflections | l = −18→18 |
13028 independent reflections | 3 standard reflections every 120 min |
4745 reflections with I > 2σ(I) | intensity decay: 12% |
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)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.209 | w = 1/[σ2(Fo2) + (0.1209P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.83 | (Δ/σ)max = 0.121 |
13028 reflections | Δρmax = 0.52 e Å−3 |
973 parameters | Δρmin = −0.31 e Å−3 |
43 restraints | Absolute structure: (Flack, 1983), 6232 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 2.7 (19) |
C20H21N3O3·0.25CH4O | V = 3724.3 (8) Å3 |
Mr = 359.41 | Z = 8 |
Monoclinic, P21 | Mo Kα radiation |
a = 15.222 (2) Å | µ = 0.09 mm−1 |
b = 16.848 (2) Å | T = 298 K |
c = 15.930 (2) Å | 0.6 × 0.3 × 0.3 mm |
β = 114.27 (1)° |
Enraf-Nonius CAD-4 diffractometer | Rint = 0.028 |
14273 measured reflections | 3 standard reflections every 120 min |
13028 independent reflections | intensity decay: 12% |
4745 reflections with I > 2σ(I) |
R[F2 > 2σ(F2)] = 0.064 | H-atom parameters constrained |
wR(F2) = 0.209 | (Δ/σ)max = 0.121 |
S = 0.83 | Δρmax = 0.52 e Å−3 |
13028 reflections | Δρmin = −0.31 e Å−3 |
973 parameters | Absolute structure: (Flack, 1983), 6232 Friedel pairs |
43 restraints | Absolute structure parameter: 2.7 (19) |
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. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 7.5342 (0.0330) x + 0.2845 (0.0380) y + 9.3753 (0.0320) z = 12.3078 (0.0221) * 0.0002 (0.0062) N101 * 0.0109 (0.0064) C102 * -0.0269 (0.0062) C103 * 0.0006 (0.0070) C104 * -0.0153 (0.0071) C105 * 0.0141 (0.0068) C106 * -0.0086 (0.0066) C107 * -0.0141 (0.0079) C108 * 0.0391 (0.0075) C109 - 0.0699 (0.0118) C110 - 0.1188 (0.0122) C119 - 0.0409 (0.0104) O101 0.0102 (0.0139) C123 Rms deviation of fitted atoms = 0.0185 5.9561 (0.0300) x - 1.8093 (0.0316) y + 10.7109 (0.0240) z = 5.6023 (0.0407) Angle to previous plane (with approximate e.s.d.) = 9.64 (0.37) * 0.0182 (0.0052) N201 * -0.0234 (0.0059) C202 * -0.0120 (0.0056) C203 * 0.0165 (0.0059) C204 * -0.0138 (0.0058) C205 * -0.0131 (0.0057) C206 * 0.0019 (0.0060) C207 * 0.0038 (0.0069) C208 * 0.0219 (0.0072) C209 0.0491 (0.0102) C210 - 0.0121 (0.0097) C219 - 0.0681 (0.0096) O201 - 0.0168 (0.0123) C223 Rms deviation of fitted atoms = 0.0155 10.4738 (0.0236) x - 0.5419 (0.0326) y + 6.0222 (0.0320) z = 7.6391 (0.0228) Angle to previous plane (with approximate e.s.d.) = 20.73 (0.31) * 0.0077 (0.0046) N301 * 0.0262 (0.0049) C302 * -0.0287 (0.0054) C303 * 0.0372 (0.0063) C304 * -0.0122 (0.0065) C305 * 0.0101 (0.0064) C306 * -0.0116 (0.0062) C307 * -0.0068 (0.0068) C308 * -0.0217 (0.0060) C309 - 0.1332 (0.0099) C310 0.0540 (0.0091) C319 - 0.0004 (0.0100) O301 0.2314 (0.0122) C323 Rms deviation of fitted atoms = 0.0207 11.6518 (0.0195) x - 1.0949 (0.0317) y + 4.2850 (0.0316) z = 10.4557 (0.0235) Angle to previous plane (with approximate e.s.d.) = 6.84 (0.35) * -0.0047 (0.0049) N401 * -0.0472 (0.0051) C402 * -0.0044 (0.0053) C403 * 0.0223 (0.0055) C404 * -0.0432 (0.0058) C405 * -0.0216 (0.0060) C406 * 0.0102 (0.0057) C407 * 0.0490 (0.0066) C408 * 0.0395 (0.0063) C409 0.0642 (0.0099) C410 - 0.1375 (0.0097) C419 - 0.0393 (0.0090) O401 - 0.1244 (0.0117) C423 Rms deviation of fitted atoms = 0.0319 |
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 | ||
N313 | 0.3176 (4) | 0.8772 (3) | 0.6824 (4) | 0.0434 (15) | |
H313 | 0.3063 | 0.9069 | 0.7207 | 0.056* | |
O303 | 0.3073 (4) | 0.7653 (3) | 0.7550 (4) | 0.0621 (16) | |
N301 | 0.4542 (4) | 0.5291 (3) | 0.5274 (4) | 0.0443 (16) | |
H301 | 0.4756 | 0.5125 | 0.4882 | 0.058* | |
O302 | 0.4571 (4) | 0.9263 (3) | 0.5635 (4) | 0.0664 (15) | |
N316 | 0.4327 (4) | 0.8067 (3) | 0.6135 (4) | 0.0391 (14) | |
O301 | 0.3755 (5) | 0.2854 (3) | 0.6410 (5) | 0.092 (2) | |
O203 | 0.7523 (3) | 0.4610 (3) | 0.2024 (4) | 0.0548 (15) | |
N216 | 0.8783 (4) | 0.4202 (3) | 0.0567 (4) | 0.0470 (16) | |
O201 | 0.9150 (5) | 0.9362 (3) | 0.1660 (4) | 0.088 (2) | |
N201 | 1.0123 (4) | 0.6886 (3) | 0.0782 (4) | 0.0537 (17) | |
H201 | 1.0553 | 0.7034 | 0.0596 | 0.070* | |
N213 | 0.8009 (4) | 0.3453 (3) | 0.1624 (4) | 0.0536 (18) | |
H213 | 0.7569 | 0.3184 | 0.1703 | 0.070* | |
O202 | 0.9021 (4) | 0.2999 (3) | 0.0088 (4) | 0.0704 (17) | |
O403 | 0.6676 (4) | 0.0549 (3) | 0.7304 (4) | 0.0561 (14) | |
N416 | 0.5351 (4) | 0.0198 (3) | 0.8686 (4) | 0.0367 (14) | |
N113 | 0.7739 (4) | −0.0177 (3) | 0.6388 (4) | 0.0526 (17) | |
H113 | 0.7348 | 0.0054 | 0.6575 | 0.068* | |
O103 | 0.7475 (3) | −0.1303 (3) | 0.6971 (4) | 0.0605 (15) | |
O401 | 0.6259 (4) | 0.5364 (3) | 0.8661 (5) | 0.0719 (17) | |
N413 | 0.6438 (4) | −0.0569 (3) | 0.7941 (4) | 0.0430 (15) | |
H413 | 0.6597 | −0.0843 | 0.7570 | 0.056* | |
N401 | 0.5617 (4) | 0.2932 (3) | 0.9864 (4) | 0.0519 (17) | |
H401 | 0.5469 | 0.3107 | 1.0296 | 0.067* | |
O402 | 0.4924 (4) | −0.0983 (3) | 0.9052 (4) | 0.0575 (14) | |
N101 | 0.9706 (5) | −0.3650 (4) | 0.5439 (5) | 0.072 (2) | |
H101 | 1.0053 | −0.3824 | 0.5168 | 0.094* | |
O102 | 0.9438 (6) | 0.0326 (4) | 0.5508 (7) | 0.154 (4) | |
O101 | 0.8637 (4) | −0.6068 (3) | 0.6327 (4) | 0.0787 (18) | |
N116 | 0.9118 (6) | −0.0854 (4) | 0.5950 (7) | 0.114 (4) | |
O501 | 0.2435 (5) | 0.2437 (4) | 0.1973 (6) | 0.114 (2) | |
H501 | 0.2379 | 0.2798 | 0.2293 | 0.159* | |
C102 | 0.9556 (6) | −0.2853 (4) | 0.5547 (6) | 0.058 (2) | |
C103 | 0.8956 (5) | −0.2812 (4) | 0.5987 (6) | 0.048 (2) | |
C104 | 0.8242 (6) | −0.3979 (5) | 0.6626 (6) | 0.068 (3) | |
H104 | 0.7904 | −0.3663 | 0.6872 | 0.089* | |
C105 | 0.8190 (6) | −0.4786 (5) | 0.6675 (7) | 0.068 (3) | |
H105 | 0.7819 | −0.5020 | 0.6948 | 0.089* | |
C106 | 0.8695 (6) | −0.5244 (4) | 0.6315 (6) | 0.062 (2) | |
C107 | 0.9206 (6) | −0.4950 (4) | 0.5871 (6) | 0.058 (2) | |
H107 | 0.9522 | −0.5280 | 0.5615 | 0.076* | |
C108 | 0.9240 (6) | −0.4127 (5) | 0.5813 (6) | 0.060 (2) | |
C109 | 0.8793 (6) | −0.3619 (4) | 0.6213 (6) | 0.050 (2) | |
C110 | 0.8543 (5) | −0.2155 (5) | 0.6254 (6) | 0.058 (2) | |
H110 | 0.8159 | −0.2336 | 0.6542 | 0.075* | |
C111 | 0.8525 (6) | −0.1360 (5) | 0.6225 (6) | 0.066 (3) | |
C112 | 0.7895 (5) | −0.0936 (4) | 0.6572 (5) | 0.046 (2) | |
C114 | 0.8157 (5) | 0.0308 (4) | 0.5904 (5) | 0.0520 (19) | |
H114 | 0.7645 | 0.0432 | 0.5300 | 0.068* | |
C115 | 0.8919 (8) | −0.0057 (5) | 0.5752 (10) | 0.109 (5) | |
C122 | 0.8465 (9) | 0.1067 (6) | 0.6419 (10) | 0.133 (5) | |
H12G | 0.9117 | 0.1019 | 0.6869 | 0.186* | |
H12H | 0.8051 | 0.1186 | 0.6723 | 0.186* | |
H12I | 0.8425 | 0.1487 | 0.5997 | 0.186* | |
C119 | 0.9905 (6) | −0.2202 (5) | 0.5108 (6) | 0.062 (2) | |
C120 | 1.0611 (8) | −0.2543 (5) | 0.4758 (8) | 0.108 (4) | |
H12A | 1.0818 | −0.2132 | 0.4462 | 0.151* | |
H12B | 1.0304 | −0.2959 | 0.4324 | 0.151* | |
H12C | 1.1159 | −0.2754 | 0.5265 | 0.151* | |
C121 | 0.9032 (8) | −0.1752 (7) | 0.4382 (6) | 0.123 (5) | |
H12D | 0.8744 | −0.1420 | 0.4690 | 0.172* | |
H12E | 0.8565 | −0.2128 | 0.4000 | 0.172* | |
H12F | 0.9248 | −0.1428 | 0.4007 | 0.172* | |
C118 | 1.0484 (6) | −0.1660 (5) | 0.5881 (7) | 0.069 (3) | |
H118 | 1.1145 | −0.1748 | 0.6139 | 0.090* | |
C117 | 1.0197 (6) | −0.1097 (6) | 0.6233 (6) | 0.088 (3) | |
H117 | 1.0664 | −0.0803 | 0.6697 | 0.114* | |
C123 | 0.8131 (7) | −0.6425 (5) | 0.6800 (7) | 0.087 (3) | |
H12J | 0.8367 | −0.6220 | 0.7415 | 0.122* | |
H12K | 0.8226 | −0.6990 | 0.6821 | 0.122* | |
H12L | 0.7456 | −0.6309 | 0.6483 | 0.122* | |
C202 | 0.9826 (5) | 0.6127 (4) | 0.0780 (5) | 0.0477 (19) | |
C203 | 0.9160 (5) | 0.6106 (4) | 0.1157 (5) | 0.0420 (19) | |
C204 | 0.8478 (5) | 0.7249 (4) | 0.1756 (5) | 0.0465 (19) | |
H204 | 0.8085 | 0.6934 | 0.1937 | 0.060* | |
C205 | 0.8481 (5) | 0.8073 (5) | 0.1865 (5) | 0.057 (2) | |
H205 | 0.8082 | 0.8306 | 0.2107 | 0.074* | |
C206 | 0.9099 (5) | 0.8556 (5) | 0.1603 (5) | 0.053 (2) | |
C207 | 0.9690 (5) | 0.8201 (5) | 0.1229 (5) | 0.058 (2) | |
H207 | 1.0104 | 0.8497 | 0.1056 | 0.076* | |
C208 | 0.9623 (5) | 0.7391 (4) | 0.1132 (5) | 0.048 (2) | |
C209 | 0.9049 (5) | 0.6906 (4) | 0.1386 (6) | 0.054 (2) | |
C210 | 0.8668 (5) | 0.5456 (4) | 0.1378 (5) | 0.0406 (18) | |
H210 | 0.8377 | 0.5620 | 0.1760 | 0.053* | |
C211 | 0.8516 (5) | 0.4662 (4) | 0.1174 (5) | 0.042 (2) | |
C212 | 0.7964 (5) | 0.4269 (5) | 0.1632 (6) | 0.055 (2) | |
C214 | 0.8778 (6) | 0.3027 (4) | 0.1485 (5) | 0.054 (2) | |
H214 | 0.9384 | 0.3090 | 0.2032 | 0.071* | |
C215 | 0.8874 (5) | 0.3408 (4) | 0.0665 (6) | 0.052 (2) | |
C222 | 0.8526 (9) | 0.2154 (5) | 0.1333 (9) | 0.119 (5) | |
H22G | 0.8331 | 0.1967 | 0.1801 | 0.167* | |
H22H | 0.9079 | 0.1860 | 0.1365 | 0.167* | |
H22I | 0.8007 | 0.2081 | 0.0738 | 0.167* | |
C219 | 1.0233 (5) | 0.5434 (4) | 0.0447 (5) | 0.0451 (19) | |
C220 | 1.0910 (6) | 0.5732 (5) | −0.0016 (6) | 0.077 (3) | |
H22A | 1.0565 | 0.6101 | −0.0499 | 0.107* | |
H22B | 1.1113 | 0.5287 | −0.0269 | 0.107* | |
H22C | 1.1464 | 0.5989 | 0.0437 | 0.107* | |
C221 | 1.0799 (5) | 0.4864 (4) | 0.1207 (5) | 0.056 (2) | |
H22D | 1.1396 | 0.5106 | 0.1606 | 0.078* | |
H22E | 1.0929 | 0.4389 | 0.0945 | 0.078* | |
H22F | 1.0431 | 0.4733 | 0.1555 | 0.078* | |
C218 | 0.9362 (5) | 0.5069 (3) | −0.0349 (5) | 0.0429 (19) | |
H218 | 0.9255 | 0.5231 | −0.0941 | 0.056* | |
C217 | 0.8743 (4) | 0.4542 (4) | −0.0272 (5) | 0.0408 (17) | |
H217 | 0.8238 | 0.4381 | −0.0815 | 0.053* | |
C223 | 0.8612 (7) | 0.9760 (5) | 0.2074 (7) | 0.086 (3) | |
H22J | 0.7940 | 0.9646 | 0.1737 | 0.120* | |
H22K | 0.8716 | 1.0322 | 0.2068 | 0.120* | |
H22L | 0.8816 | 0.9583 | 0.2699 | 0.120* | |
C302 | 0.4483 (4) | 0.6068 (4) | 0.5478 (5) | 0.0335 (17) | |
C303 | 0.4075 (5) | 0.6122 (4) | 0.6101 (5) | 0.0391 (19) | |
C304 | 0.3604 (5) | 0.4960 (4) | 0.6925 (6) | 0.059 (2) | |
H304 | 0.3456 | 0.5273 | 0.7330 | 0.077* | |
C305 | 0.3510 (6) | 0.4141 (5) | 0.6933 (6) | 0.066 (3) | |
H305 | 0.3240 | 0.3909 | 0.7302 | 0.086* | |
C306 | 0.3812 (5) | 0.3676 (4) | 0.6403 (6) | 0.060 (3) | |
C307 | 0.4149 (6) | 0.3994 (5) | 0.5809 (6) | 0.059 (2) | |
H307 | 0.4332 | 0.3674 | 0.5433 | 0.077* | |
C308 | 0.4209 (5) | 0.4801 (4) | 0.5785 (6) | 0.048 (2) | |
C309 | 0.3920 (4) | 0.5312 (4) | 0.6309 (5) | 0.0360 (18) | |
C310 | 0.3772 (5) | 0.6781 (4) | 0.6515 (5) | 0.0407 (18) | |
H310 | 0.3467 | 0.6603 | 0.6879 | 0.053* | |
C311 | 0.3815 (5) | 0.7571 (4) | 0.6508 (5) | 0.048 (2) | |
C312 | 0.3335 (5) | 0.8001 (4) | 0.7013 (6) | 0.044 (2) | |
C314 | 0.3185 (5) | 0.9129 (4) | 0.6005 (5) | 0.0459 (19) | |
H314 | 0.2612 | 0.8952 | 0.5473 | 0.060* | |
C315 | 0.4059 (5) | 0.8837 (4) | 0.5894 (5) | 0.0454 (19) | |
C322 | 0.3158 (6) | 1.0029 (4) | 0.6059 (6) | 0.071 (3) | |
H32G | 0.2626 | 1.0186 | 0.6198 | 0.100* | |
H32H | 0.3081 | 1.0253 | 0.5478 | 0.100* | |
H32I | 0.3749 | 1.0216 | 0.6533 | 0.100* | |
C319 | 0.4804 (5) | 0.6724 (4) | 0.5025 (5) | 0.0438 (19) | |
C320 | 0.5382 (7) | 0.6385 (5) | 0.4513 (7) | 0.081 (3) | |
H32A | 0.5922 | 0.6090 | 0.4935 | 0.114* | |
H32B | 0.5609 | 0.6812 | 0.4255 | 0.114* | |
H32C | 0.4977 | 0.6041 | 0.4028 | 0.114* | |
C321 | 0.3935 (5) | 0.7178 (4) | 0.4337 (5) | 0.060 (2) | |
H32D | 0.3616 | 0.6860 | 0.3796 | 0.084* | |
H32E | 0.4149 | 0.7665 | 0.4171 | 0.084* | |
H32F | 0.3495 | 0.7293 | 0.4613 | 0.084* | |
C318 | 0.5475 (5) | 0.7260 (4) | 0.5799 (5) | 0.049 (2) | |
H318 | 0.6129 | 0.7176 | 0.5968 | 0.064* | |
C317 | 0.5272 (5) | 0.7810 (4) | 0.6253 (5) | 0.050 (2) | |
H317 | 0.5791 | 0.8067 | 0.6705 | 0.065* | |
C323 | 0.3563 (6) | 0.2467 (5) | 0.7095 (7) | 0.078 (3) | |
H32J | 0.3973 | 0.2677 | 0.7687 | 0.109* | |
H32K | 0.3682 | 0.1909 | 0.7079 | 0.109* | |
H32L | 0.2901 | 0.2549 | 0.6987 | 0.109* | |
C402 | 0.5593 (5) | 0.2135 (4) | 0.9627 (5) | 0.0439 (19) | |
C403 | 0.5895 (5) | 0.2104 (4) | 0.8897 (5) | 0.0399 (19) | |
C404 | 0.6341 (5) | 0.3265 (4) | 0.8044 (4) | 0.0397 (18) | |
H404 | 0.6489 | 0.2952 | 0.7638 | 0.052* | |
C405 | 0.6377 (5) | 0.4076 (4) | 0.8002 (5) | 0.054 (2) | |
H405 | 0.6516 | 0.4313 | 0.7544 | 0.071* | |
C406 | 0.6207 (5) | 0.4550 (5) | 0.8634 (6) | 0.054 (2) | |
C407 | 0.5955 (5) | 0.4224 (4) | 0.9312 (6) | 0.049 (2) | |
H407 | 0.5828 | 0.4541 | 0.9727 | 0.064* | |
C408 | 0.5903 (5) | 0.3398 (4) | 0.9332 (5) | 0.0401 (18) | |
C409 | 0.6082 (5) | 0.2913 (4) | 0.8699 (5) | 0.048 (2) | |
C410 | 0.6063 (5) | 0.1432 (4) | 0.8431 (5) | 0.046 (2) | |
H410 | 0.6379 | 0.1598 | 0.8071 | 0.059* | |
C411 | 0.5920 (4) | 0.0652 (4) | 0.8336 (5) | 0.0358 (18) | |
C412 | 0.6371 (5) | 0.0211 (4) | 0.7827 (5) | 0.0457 (19) | |
C414 | 0.6262 (5) | −0.0989 (4) | 0.8641 (5) | 0.0419 (18) | |
H414 | 0.6038 | −0.1522 | 0.8403 | 0.054* | |
C415 | 0.5452 (5) | −0.0585 (4) | 0.8810 (5) | 0.0394 (17) | |
C422 | 0.7133 (6) | −0.1085 (5) | 0.9521 (5) | 0.082 (3) | |
H42G | 0.7608 | −0.1391 | 0.9412 | 0.115* | |
H42H | 0.6960 | −0.1353 | 0.9962 | 0.115* | |
H42I | 0.7394 | −0.0572 | 0.9755 | 0.115* | |
C419 | 0.5284 (5) | 0.1488 (4) | 1.0092 (5) | 0.0437 (19) | |
C420 | 0.4890 (7) | 0.1827 (5) | 1.0757 (6) | 0.075 (3) | |
H42A | 0.5353 | 0.2186 | 1.1176 | 0.105* | |
H42B | 0.4769 | 0.1402 | 1.1097 | 0.105* | |
H42C | 0.4300 | 0.2106 | 1.0416 | 0.105* | |
C421 | 0.6106 (6) | 0.0954 (5) | 1.0622 (5) | 0.065 (2) | |
H42D | 0.6437 | 0.0810 | 1.0245 | 0.091* | |
H42E | 0.5868 | 0.0484 | 1.0798 | 0.091* | |
H42F | 0.6543 | 0.1224 | 1.1163 | 0.091* | |
C418 | 0.4491 (5) | 0.1077 (4) | 0.9325 (5) | 0.0470 (19) | |
H418 | 0.3876 | 0.1238 | 0.9241 | 0.061* | |
C417 | 0.4506 (5) | 0.0522 (4) | 0.8739 (5) | 0.0471 (19) | |
H417 | 0.3914 | 0.0326 | 0.8327 | 0.061* | |
C423 | 0.6467 (6) | 0.5742 (5) | 0.7993 (7) | 0.080 (3) | |
H42J | 0.7071 | 0.5551 | 0.8018 | 0.112* | |
H42K | 0.6507 | 0.6304 | 0.8102 | 0.112* | |
H42L | 0.5966 | 0.5633 | 0.7397 | 0.112* | |
C502 | 0.1553 (8) | 0.2274 (6) | 0.1279 (8) | 0.138 (5) | |
H50A | 0.1073 | 0.2258 | 0.1524 | 0.193* | |
H50B | 0.1578 | 0.1769 | 0.1010 | 0.193* | |
H50C | 0.1391 | 0.2679 | 0.0816 | 0.193* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N313 | 0.053 (3) | 0.032 (3) | 0.054 (4) | 0.005 (3) | 0.030 (3) | 0.001 (3) |
O303 | 0.080 (4) | 0.044 (3) | 0.098 (5) | 0.002 (3) | 0.073 (4) | 0.006 (3) |
N301 | 0.057 (4) | 0.032 (4) | 0.059 (4) | −0.004 (3) | 0.040 (3) | −0.010 (3) |
O302 | 0.087 (4) | 0.046 (3) | 0.089 (4) | −0.005 (3) | 0.059 (4) | 0.001 (3) |
N316 | 0.044 (3) | 0.035 (4) | 0.054 (4) | 0.004 (3) | 0.035 (3) | 0.004 (3) |
O301 | 0.150 (6) | 0.033 (4) | 0.134 (6) | 0.000 (4) | 0.099 (5) | 0.014 (4) |
O203 | 0.061 (3) | 0.041 (3) | 0.087 (4) | 0.007 (2) | 0.055 (3) | 0.011 (3) |
N216 | 0.044 (4) | 0.037 (4) | 0.072 (5) | −0.004 (3) | 0.036 (4) | 0.000 (3) |
O201 | 0.137 (6) | 0.030 (3) | 0.114 (5) | −0.008 (4) | 0.068 (5) | −0.005 (3) |
N201 | 0.054 (4) | 0.042 (4) | 0.085 (5) | −0.009 (3) | 0.049 (4) | 0.004 (3) |
N213 | 0.065 (4) | 0.041 (4) | 0.084 (5) | −0.011 (3) | 0.060 (4) | 0.005 (3) |
O202 | 0.089 (4) | 0.049 (3) | 0.108 (5) | −0.006 (3) | 0.075 (4) | −0.013 (3) |
O403 | 0.088 (4) | 0.029 (3) | 0.074 (4) | 0.008 (3) | 0.056 (3) | 0.006 (3) |
N416 | 0.036 (3) | 0.018 (3) | 0.063 (4) | −0.006 (2) | 0.027 (3) | −0.001 (3) |
N113 | 0.061 (4) | 0.041 (4) | 0.082 (5) | −0.003 (3) | 0.054 (4) | 0.002 (3) |
O103 | 0.075 (3) | 0.039 (3) | 0.104 (4) | −0.011 (3) | 0.074 (3) | 0.000 (3) |
O401 | 0.111 (4) | 0.024 (3) | 0.117 (5) | −0.008 (3) | 0.083 (4) | −0.005 (3) |
N413 | 0.063 (4) | 0.026 (3) | 0.048 (4) | 0.003 (3) | 0.031 (3) | −0.009 (3) |
N401 | 0.069 (4) | 0.030 (4) | 0.074 (5) | −0.004 (3) | 0.048 (4) | −0.008 (3) |
O402 | 0.074 (3) | 0.032 (3) | 0.084 (4) | −0.005 (2) | 0.050 (3) | 0.005 (3) |
N101 | 0.096 (5) | 0.053 (4) | 0.112 (6) | −0.001 (4) | 0.088 (5) | −0.008 (4) |
O102 | 0.217 (8) | 0.058 (4) | 0.313 (12) | 0.010 (5) | 0.236 (9) | 0.030 (6) |
O101 | 0.103 (4) | 0.039 (4) | 0.128 (5) | −0.005 (3) | 0.082 (4) | 0.001 (3) |
N116 | 0.146 (8) | 0.048 (5) | 0.240 (11) | 0.008 (4) | 0.171 (8) | 0.024 (6) |
O501 | 0.109 (6) | 0.090 (6) | 0.138 (7) | 0.008 (4) | 0.046 (5) | −0.027 (4) |
C102 | 0.071 (6) | 0.026 (4) | 0.090 (7) | 0.001 (4) | 0.046 (5) | −0.008 (4) |
C103 | 0.055 (5) | 0.029 (4) | 0.081 (6) | 0.006 (3) | 0.049 (5) | 0.002 (4) |
C104 | 0.072 (6) | 0.048 (6) | 0.116 (8) | −0.002 (4) | 0.068 (6) | −0.006 (5) |
C105 | 0.078 (6) | 0.043 (5) | 0.114 (8) | −0.019 (4) | 0.070 (6) | −0.021 (5) |
C106 | 0.077 (6) | 0.020 (4) | 0.096 (7) | −0.002 (4) | 0.042 (6) | −0.005 (4) |
C107 | 0.071 (6) | 0.037 (5) | 0.089 (7) | 0.004 (4) | 0.055 (5) | −0.010 (4) |
C108 | 0.062 (5) | 0.050 (5) | 0.084 (6) | 0.005 (4) | 0.046 (5) | −0.003 (4) |
C109 | 0.073 (5) | 0.031 (4) | 0.071 (6) | 0.007 (4) | 0.056 (5) | 0.000 (4) |
C110 | 0.063 (5) | 0.038 (5) | 0.092 (7) | −0.004 (4) | 0.053 (5) | −0.002 (4) |
C111 | 0.071 (6) | 0.060 (6) | 0.094 (7) | 0.003 (4) | 0.061 (6) | 0.014 (5) |
C112 | 0.057 (5) | 0.022 (4) | 0.073 (6) | 0.004 (3) | 0.043 (4) | −0.007 (4) |
C114 | 0.051 (4) | 0.052 (5) | 0.053 (5) | 0.000 (4) | 0.023 (4) | 0.000 (4) |
C115 | 0.115 (8) | 0.049 (6) | 0.232 (14) | −0.001 (5) | 0.142 (9) | 0.027 (7) |
C122 | 0.210 (13) | 0.050 (7) | 0.212 (14) | −0.025 (7) | 0.160 (12) | 0.001 (8) |
C119 | 0.097 (6) | 0.059 (6) | 0.074 (6) | −0.033 (5) | 0.080 (6) | −0.028 (5) |
C120 | 0.152 (9) | 0.048 (6) | 0.204 (12) | −0.015 (5) | 0.155 (9) | −0.005 (6) |
C121 | 0.160 (10) | 0.154 (11) | 0.028 (5) | −0.081 (9) | 0.013 (6) | 0.002 (6) |
C118 | 0.086 (6) | 0.051 (5) | 0.105 (7) | 0.006 (5) | 0.075 (6) | 0.003 (5) |
C117 | 0.076 (6) | 0.097 (7) | 0.091 (7) | −0.021 (6) | 0.036 (6) | −0.008 (6) |
C123 | 0.107 (7) | 0.048 (6) | 0.122 (8) | −0.015 (5) | 0.062 (7) | −0.001 (5) |
C202 | 0.068 (5) | 0.029 (4) | 0.061 (5) | −0.001 (4) | 0.042 (4) | −0.002 (4) |
C203 | 0.043 (4) | 0.043 (5) | 0.048 (5) | −0.006 (3) | 0.027 (4) | −0.001 (4) |
C204 | 0.066 (5) | 0.037 (5) | 0.047 (5) | −0.005 (4) | 0.033 (4) | −0.004 (4) |
C205 | 0.058 (5) | 0.065 (6) | 0.051 (5) | 0.005 (4) | 0.026 (5) | −0.004 (4) |
C206 | 0.065 (5) | 0.064 (6) | 0.043 (5) | 0.002 (4) | 0.034 (4) | 0.006 (4) |
C207 | 0.067 (5) | 0.044 (5) | 0.070 (6) | −0.012 (4) | 0.034 (5) | 0.005 (4) |
C208 | 0.047 (5) | 0.048 (5) | 0.062 (5) | 0.008 (4) | 0.034 (4) | 0.015 (4) |
C209 | 0.053 (5) | 0.042 (5) | 0.076 (6) | 0.000 (4) | 0.037 (5) | −0.007 (4) |
C210 | 0.039 (4) | 0.046 (5) | 0.051 (5) | 0.002 (3) | 0.032 (4) | −0.001 (4) |
C211 | 0.040 (4) | 0.032 (5) | 0.073 (6) | 0.009 (3) | 0.041 (4) | 0.010 (4) |
C212 | 0.044 (5) | 0.055 (6) | 0.077 (6) | 0.003 (4) | 0.038 (5) | 0.012 (5) |
C214 | 0.065 (5) | 0.056 (5) | 0.063 (5) | 0.008 (4) | 0.048 (5) | 0.012 (4) |
C215 | 0.067 (5) | 0.040 (5) | 0.071 (6) | 0.001 (4) | 0.050 (5) | −0.007 (4) |
C222 | 0.215 (13) | 0.036 (5) | 0.196 (12) | 0.007 (6) | 0.175 (11) | 0.009 (7) |
C219 | 0.049 (4) | 0.035 (4) | 0.055 (5) | 0.003 (3) | 0.025 (4) | 0.007 (4) |
C220 | 0.071 (6) | 0.083 (7) | 0.111 (8) | 0.011 (5) | 0.072 (6) | 0.016 (6) |
C221 | 0.048 (4) | 0.047 (4) | 0.070 (6) | 0.004 (4) | 0.023 (4) | 0.011 (4) |
C218 | 0.070 (5) | 0.020 (4) | 0.065 (5) | 0.009 (3) | 0.055 (5) | 0.005 (3) |
C217 | 0.047 (4) | 0.038 (4) | 0.044 (4) | 0.001 (3) | 0.025 (4) | 0.013 (3) |
C223 | 0.133 (8) | 0.036 (5) | 0.087 (7) | 0.012 (5) | 0.043 (7) | −0.013 (5) |
C302 | 0.036 (4) | 0.029 (4) | 0.043 (4) | −0.005 (3) | 0.023 (4) | −0.005 (3) |
C303 | 0.054 (5) | 0.025 (4) | 0.049 (5) | 0.007 (3) | 0.032 (4) | 0.004 (4) |
C304 | 0.075 (6) | 0.026 (5) | 0.100 (7) | −0.010 (4) | 0.058 (5) | −0.014 (4) |
C305 | 0.087 (6) | 0.057 (6) | 0.096 (7) | −0.002 (4) | 0.080 (6) | −0.010 (5) |
C306 | 0.070 (5) | 0.017 (4) | 0.109 (8) | −0.003 (4) | 0.053 (6) | 0.006 (4) |
C307 | 0.078 (6) | 0.030 (5) | 0.078 (6) | 0.001 (4) | 0.042 (5) | −0.009 (4) |
C308 | 0.041 (4) | 0.039 (5) | 0.073 (6) | 0.004 (3) | 0.034 (4) | 0.001 (4) |
C309 | 0.032 (4) | 0.046 (5) | 0.035 (4) | 0.005 (3) | 0.018 (3) | 0.004 (4) |
C310 | 0.055 (5) | 0.035 (5) | 0.048 (5) | 0.002 (3) | 0.037 (4) | 0.005 (4) |
C311 | 0.066 (5) | 0.036 (5) | 0.059 (5) | 0.004 (4) | 0.044 (5) | 0.004 (4) |
C312 | 0.047 (4) | 0.035 (5) | 0.075 (6) | −0.009 (3) | 0.048 (4) | −0.004 (4) |
C314 | 0.050 (4) | 0.037 (4) | 0.056 (5) | 0.003 (3) | 0.027 (4) | −0.002 (4) |
C315 | 0.046 (4) | 0.045 (5) | 0.051 (5) | −0.002 (4) | 0.026 (4) | −0.009 (4) |
C322 | 0.094 (6) | 0.036 (4) | 0.114 (7) | 0.008 (4) | 0.074 (6) | 0.002 (4) |
C319 | 0.042 (5) | 0.043 (5) | 0.054 (5) | 0.004 (4) | 0.028 (4) | 0.006 (4) |
C320 | 0.135 (8) | 0.038 (5) | 0.113 (8) | −0.009 (5) | 0.093 (7) | −0.013 (5) |
C321 | 0.082 (6) | 0.043 (5) | 0.045 (5) | −0.019 (4) | 0.017 (5) | −0.015 (4) |
C318 | 0.053 (5) | 0.035 (4) | 0.061 (5) | −0.004 (3) | 0.025 (4) | −0.004 (4) |
C317 | 0.043 (4) | 0.052 (5) | 0.061 (5) | −0.019 (4) | 0.027 (4) | −0.026 (4) |
C323 | 0.080 (6) | 0.045 (6) | 0.112 (8) | 0.006 (4) | 0.043 (6) | 0.029 (5) |
C402 | 0.050 (4) | 0.038 (4) | 0.041 (5) | 0.005 (4) | 0.016 (4) | −0.007 (4) |
C403 | 0.057 (5) | 0.019 (4) | 0.051 (5) | −0.011 (3) | 0.030 (4) | −0.009 (4) |
C404 | 0.054 (4) | 0.044 (5) | 0.029 (4) | −0.003 (4) | 0.025 (4) | 0.000 (4) |
C405 | 0.075 (6) | 0.032 (5) | 0.061 (5) | −0.017 (4) | 0.033 (5) | 0.001 (4) |
C406 | 0.063 (5) | 0.045 (6) | 0.065 (6) | −0.008 (4) | 0.038 (5) | −0.013 (4) |
C407 | 0.054 (5) | 0.035 (5) | 0.076 (6) | −0.004 (3) | 0.044 (4) | −0.018 (4) |
C408 | 0.065 (5) | 0.028 (4) | 0.034 (4) | −0.004 (3) | 0.029 (4) | −0.007 (3) |
C409 | 0.056 (5) | 0.039 (5) | 0.052 (5) | −0.010 (4) | 0.025 (4) | −0.016 (4) |
C410 | 0.051 (5) | 0.039 (5) | 0.057 (5) | −0.003 (3) | 0.032 (4) | −0.007 (4) |
C411 | 0.026 (4) | 0.035 (4) | 0.043 (4) | −0.005 (3) | 0.011 (3) | −0.016 (3) |
C412 | 0.061 (5) | 0.030 (4) | 0.052 (5) | 0.001 (3) | 0.029 (4) | 0.000 (4) |
C414 | 0.063 (5) | 0.028 (4) | 0.053 (5) | 0.003 (3) | 0.043 (4) | 0.008 (3) |
C415 | 0.048 (4) | 0.035 (4) | 0.046 (4) | −0.004 (3) | 0.030 (4) | 0.012 (3) |
C422 | 0.064 (5) | 0.098 (7) | 0.082 (7) | 0.030 (5) | 0.028 (5) | 0.039 (6) |
C419 | 0.059 (5) | 0.021 (4) | 0.053 (5) | 0.001 (3) | 0.025 (4) | 0.001 (3) |
C420 | 0.105 (7) | 0.085 (7) | 0.071 (6) | −0.026 (5) | 0.071 (6) | −0.005 (5) |
C421 | 0.093 (6) | 0.048 (5) | 0.051 (5) | −0.010 (5) | 0.026 (5) | 0.006 (4) |
C418 | 0.050 (4) | 0.042 (5) | 0.063 (5) | −0.007 (4) | 0.037 (4) | 0.000 (4) |
C417 | 0.045 (4) | 0.035 (4) | 0.064 (5) | −0.013 (3) | 0.025 (4) | 0.005 (4) |
C423 | 0.088 (7) | 0.038 (6) | 0.141 (9) | −0.002 (4) | 0.074 (7) | 0.012 (6) |
C502 | 0.127 (10) | 0.092 (8) | 0.133 (10) | −0.035 (7) | −0.010 (9) | −0.011 (7) |
N313—C312 | 1.333 (9) | C208—C209 | 1.373 (10) |
N313—C314 | 1.442 (8) | C210—C211 | 1.373 (9) |
N313—H313 | 0.8600 | C210—H210 | 0.9300 |
O303—C312 | 1.231 (8) | C211—C212 | 1.476 (10) |
N301—C302 | 1.361 (8) | C214—C222 | 1.515 (11) |
N301—C308 | 1.393 (9) | C214—C215 | 1.516 (10) |
N301—H301 | 0.8600 | C214—H214 | 0.9800 |
O302—C315 | 1.247 (8) | C222—H22G | 0.9600 |
N316—C315 | 1.366 (9) | C222—H22H | 0.9600 |
N316—C311 | 1.429 (8) | C222—H22I | 0.9600 |
N316—C317 | 1.438 (8) | C219—C221 | 1.508 (9) |
O301—C306 | 1.388 (9) | C219—C218 | 1.536 (10) |
O301—C323 | 1.402 (10) | C219—C220 | 1.576 (9) |
O203—C212 | 1.231 (9) | C220—H22A | 0.9600 |
N216—C215 | 1.347 (8) | C220—H22B | 0.9600 |
N216—C211 | 1.422 (9) | C220—H22C | 0.9600 |
N216—C217 | 1.432 (8) | C221—H22D | 0.9600 |
O201—C206 | 1.362 (9) | C221—H22E | 0.9600 |
O201—C223 | 1.414 (10) | C221—H22F | 0.9600 |
N201—C202 | 1.354 (8) | C218—C217 | 1.336 (8) |
N201—C208 | 1.402 (9) | C218—H218 | 0.9300 |
N201—H201 | 0.8600 | C217—H217 | 0.9300 |
N213—C212 | 1.377 (9) | C223—H22J | 0.9600 |
N213—C214 | 1.466 (8) | C223—H22K | 0.9600 |
N213—H213 | 0.8600 | C223—H22L | 0.9600 |
O202—C215 | 1.240 (8) | C302—C303 | 1.373 (9) |
O403—C412 | 1.245 (8) | C302—C319 | 1.507 (9) |
N416—C415 | 1.334 (8) | C303—C309 | 1.446 (9) |
N416—C411 | 1.430 (8) | C303—C310 | 1.459 (9) |
N416—C417 | 1.432 (8) | C304—C305 | 1.388 (10) |
N113—C112 | 1.312 (8) | C304—C309 | 1.390 (10) |
N113—C114 | 1.438 (8) | C304—H304 | 0.9300 |
N113—H113 | 0.8600 | C305—C306 | 1.362 (10) |
O103—C112 | 1.236 (8) | C305—H305 | 0.9300 |
O401—C406 | 1.374 (9) | C306—C307 | 1.359 (10) |
O401—C423 | 1.383 (10) | C307—C308 | 1.364 (10) |
N413—C412 | 1.326 (8) | C307—H307 | 0.9300 |
N413—C414 | 1.436 (7) | C308—C309 | 1.390 (10) |
N413—H413 | 0.8600 | C310—C311 | 1.332 (9) |
N401—C408 | 1.352 (8) | C310—H310 | 0.9300 |
N401—C402 | 1.391 (9) | C311—C312 | 1.479 (10) |
N401—H401 | 0.8600 | C314—C315 | 1.495 (9) |
O402—C415 | 1.223 (7) | C314—C322 | 1.519 (9) |
N101—C108 | 1.360 (9) | C314—H314 | 0.9800 |
N101—C102 | 1.385 (9) | C322—H32G | 0.9600 |
N101—H101 | 0.8600 | C322—H32H | 0.9600 |
O102—C115 | 1.200 (9) | C322—H32I | 0.9600 |
O101—C106 | 1.391 (8) | C319—C321 | 1.530 (10) |
O101—C123 | 1.414 (9) | C319—C318 | 1.530 (10) |
N116—C115 | 1.384 (11) | C319—C320 | 1.536 (10) |
N116—C111 | 1.435 (10) | C320—H32A | 0.9600 |
N116—C117 | 1.568 (12) | C320—H32B | 0.9600 |
O501—C502 | 1.372 (11) | C320—H32C | 0.9600 |
O501—H501 | 0.8200 | C321—H32D | 0.9600 |
C102—C103 | 1.363 (10) | C321—H32E | 0.9600 |
C102—C119 | 1.510 (11) | C321—H32F | 0.9600 |
C103—C110 | 1.422 (10) | C318—C317 | 1.288 (9) |
C103—C109 | 1.453 (10) | C318—H318 | 0.9300 |
C104—C105 | 1.366 (11) | C317—H317 | 0.9300 |
C104—C109 | 1.400 (10) | C323—H32J | 0.9600 |
C104—H104 | 0.9300 | C323—H32K | 0.9600 |
C105—C106 | 1.371 (10) | C323—H32L | 0.9600 |
C105—H105 | 0.9300 | C402—C403 | 1.416 (10) |
C106—C107 | 1.344 (10) | C402—C419 | 1.498 (10) |
C107—C108 | 1.392 (10) | C403—C410 | 1.434 (9) |
C107—H107 | 0.9300 | C403—C409 | 1.452 (10) |
C108—C109 | 1.401 (10) | C404—C405 | 1.371 (9) |
C110—C111 | 1.339 (10) | C404—C409 | 1.391 (9) |
C110—H110 | 0.9300 | C404—H404 | 0.9300 |
C111—C112 | 1.474 (10) | C405—C406 | 1.389 (10) |
C114—C115 | 1.420 (11) | C405—H405 | 0.9300 |
C114—C122 | 1.488 (12) | C406—C407 | 1.400 (10) |
C114—H114 | 0.9800 | C407—C408 | 1.394 (9) |
C122—H12G | 0.9600 | C407—H407 | 0.9300 |
C122—H12H | 0.9600 | C408—C409 | 1.409 (9) |
C122—H12I | 0.9600 | C410—C411 | 1.329 (9) |
C119—C118 | 1.495 (12) | C410—H410 | 0.9300 |
C119—C120 | 1.513 (10) | C411—C412 | 1.462 (9) |
C119—C121 | 1.554 (13) | C414—C422 | 1.491 (10) |
C120—H12A | 0.9600 | C414—C415 | 1.526 (9) |
C120—H12B | 0.9600 | C414—H414 | 0.9800 |
C120—H12C | 0.9600 | C422—H42G | 0.9600 |
C121—H12D | 0.9600 | C422—H42H | 0.9600 |
C121—H12E | 0.9600 | C422—H42I | 0.9600 |
C121—H12F | 0.9600 | C419—C418 | 1.489 (10) |
C118—C117 | 1.267 (11) | C419—C421 | 1.490 (10) |
C118—H118 | 0.9300 | C419—C420 | 1.526 (10) |
C117—H117 | 0.9300 | C420—H42A | 0.9600 |
C123—H12J | 0.9600 | C420—H42B | 0.9600 |
C123—H12K | 0.9600 | C420—H42C | 0.9600 |
C123—H12L | 0.9600 | C421—H42D | 0.9600 |
C202—C203 | 1.375 (9) | C421—H42E | 0.9600 |
C202—C219 | 1.516 (10) | C421—H42F | 0.9600 |
C203—C209 | 1.423 (10) | C418—C417 | 1.328 (9) |
C203—C210 | 1.450 (9) | C418—H418 | 0.9300 |
C204—C209 | 1.363 (10) | C417—H417 | 0.9300 |
C204—C205 | 1.399 (10) | C423—H42J | 0.9600 |
C204—H204 | 0.9300 | C423—H42K | 0.9600 |
C205—C206 | 1.430 (10) | C423—H42L | 0.9600 |
C205—H205 | 0.9300 | C502—H50A | 0.9600 |
C206—C207 | 1.401 (10) | C502—H50B | 0.9600 |
C207—C208 | 1.372 (10) | C502—H50C | 0.9600 |
C207—H207 | 0.9300 | ||
C312—N313—C314 | 122.9 (6) | C219—C221—H22E | 109.5 |
C312—N313—H313 | 118.5 | H22D—C221—H22E | 109.5 |
C314—N313—H313 | 118.5 | C219—C221—H22F | 109.5 |
C302—N301—C308 | 110.7 (6) | H22D—C221—H22F | 109.5 |
C302—N301—H301 | 124.7 | H22E—C221—H22F | 109.5 |
C308—N301—H301 | 124.7 | C217—C218—C219 | 126.3 (7) |
C315—N316—C311 | 121.4 (6) | C217—C218—H218 | 116.9 |
C315—N316—C317 | 119.3 (6) | C219—C218—H218 | 116.9 |
C311—N316—C317 | 117.1 (6) | C218—C217—N216 | 126.2 (7) |
C306—O301—C323 | 120.2 (8) | C218—C217—H217 | 116.9 |
C215—N216—C211 | 120.5 (7) | N216—C217—H217 | 116.9 |
C215—N216—C217 | 117.9 (6) | O201—C223—H22J | 109.5 |
C211—N216—C217 | 120.1 (5) | O201—C223—H22K | 109.5 |
C206—O201—C223 | 118.4 (7) | H22J—C223—H22K | 109.5 |
C202—N201—C208 | 109.8 (6) | O201—C223—H22L | 109.5 |
C202—N201—H201 | 125.1 | H22J—C223—H22L | 109.5 |
C208—N201—H201 | 125.1 | H22K—C223—H22L | 109.5 |
C212—N213—C214 | 122.4 (6) | N301—C302—C303 | 109.4 (6) |
C212—N213—H213 | 118.8 | N301—C302—C319 | 121.6 (6) |
C214—N213—H213 | 118.8 | C303—C302—C319 | 128.9 (6) |
C415—N416—C411 | 122.4 (6) | C302—C303—C309 | 105.5 (6) |
C415—N416—C417 | 114.8 (5) | C302—C303—C310 | 134.3 (6) |
C411—N416—C417 | 121.5 (5) | C309—C303—C310 | 120.2 (6) |
C112—N113—C114 | 126.4 (6) | C305—C304—C309 | 119.9 (8) |
C112—N113—H113 | 116.8 | C305—C304—H304 | 120.0 |
C114—N113—H113 | 116.8 | C309—C304—H304 | 120.0 |
C406—O401—C423 | 117.6 (7) | C306—C305—C304 | 120.2 (8) |
C412—N413—C414 | 124.5 (6) | C306—C305—H305 | 119.9 |
C412—N413—H413 | 117.8 | C304—C305—H305 | 119.9 |
C414—N413—H413 | 117.8 | C307—C306—C305 | 121.6 (7) |
C408—N401—C402 | 111.7 (6) | C307—C306—O301 | 116.2 (8) |
C408—N401—H401 | 124.1 | C305—C306—O301 | 122.1 (8) |
C402—N401—H401 | 124.1 | C306—C307—C308 | 117.5 (8) |
C108—N101—C102 | 112.2 (7) | C306—C307—H307 | 121.2 |
C108—N101—H101 | 123.9 | C308—C307—H307 | 121.2 |
C102—N101—H101 | 123.9 | C307—C308—C309 | 124.0 (8) |
C106—O101—C123 | 118.9 (7) | C307—C308—N301 | 130.6 (8) |
C115—N116—C111 | 122.8 (7) | C309—C308—N301 | 105.4 (6) |
C115—N116—C117 | 115.0 (7) | C308—C309—C304 | 116.5 (7) |
C111—N116—C117 | 118.2 (7) | C308—C309—C303 | 109.0 (6) |
C502—O501—H501 | 109.5 | C304—C309—C303 | 134.4 (7) |
C103—C102—N101 | 106.9 (7) | C311—C310—C303 | 137.0 (7) |
C103—C102—C119 | 129.8 (7) | C311—C310—H310 | 111.5 |
N101—C102—C119 | 122.7 (7) | C303—C310—H310 | 111.5 |
C102—C103—C110 | 131.6 (7) | C310—C311—N316 | 128.6 (7) |
C102—C103—C109 | 107.4 (6) | C310—C311—C312 | 116.6 (7) |
C110—C103—C109 | 120.9 (7) | N316—C311—C312 | 114.5 (6) |
C105—C104—C109 | 121.1 (8) | O303—C312—N313 | 122.7 (7) |
C105—C104—H104 | 119.4 | O303—C312—C311 | 121.2 (7) |
C109—C104—H104 | 119.4 | N313—C312—C311 | 116.0 (7) |
C104—C105—C106 | 118.9 (8) | N313—C314—C315 | 108.0 (6) |
C104—C105—H105 | 120.6 | N313—C314—C322 | 110.8 (6) |
C106—C105—H105 | 120.6 | C315—C314—C322 | 112.4 (6) |
C107—C106—C105 | 123.9 (7) | N313—C314—H314 | 108.5 |
C107—C106—O101 | 115.4 (7) | C315—C314—H314 | 108.5 |
C105—C106—O101 | 120.5 (8) | C322—C314—H314 | 108.5 |
C106—C107—C108 | 116.6 (7) | O302—C315—N316 | 119.0 (6) |
C106—C107—H107 | 121.7 | O302—C315—C314 | 123.8 (7) |
C108—C107—H107 | 121.7 | N316—C315—C314 | 117.2 (6) |
N101—C108—C107 | 131.1 (8) | C314—C322—H32G | 109.5 |
N101—C108—C109 | 106.0 (7) | C314—C322—H32H | 109.5 |
C107—C108—C109 | 122.7 (8) | H32G—C322—H32H | 109.5 |
C104—C109—C108 | 116.6 (7) | C314—C322—H32I | 109.5 |
C104—C109—C103 | 135.9 (7) | H32G—C322—H32I | 109.5 |
C108—C109—C103 | 107.1 (7) | H32H—C322—H32I | 109.5 |
C111—C110—C103 | 140.7 (8) | C302—C319—C321 | 110.8 (5) |
C111—C110—H110 | 109.7 | C302—C319—C318 | 106.7 (6) |
C103—C110—H110 | 109.7 | C321—C319—C318 | 112.1 (6) |
C110—C111—N116 | 126.8 (8) | C302—C319—C320 | 110.5 (6) |
C110—C111—C112 | 118.6 (7) | C321—C319—C320 | 108.7 (7) |
N116—C111—C112 | 114.4 (7) | C318—C319—C320 | 108.0 (6) |
O103—C112—N113 | 121.2 (7) | C319—C320—H32A | 109.5 |
O103—C112—C111 | 120.3 (7) | C319—C320—H32B | 109.5 |
N113—C112—C111 | 118.4 (7) | H32A—C320—H32B | 109.5 |
C115—C114—N113 | 114.8 (7) | C319—C320—H32C | 109.5 |
C115—C114—C122 | 111.8 (8) | H32A—C320—H32C | 109.5 |
N113—C114—C122 | 107.6 (7) | H32B—C320—H32C | 109.5 |
C115—C114—H114 | 107.5 | C319—C321—H32D | 109.5 |
N113—C114—H114 | 107.5 | C319—C321—H32E | 109.5 |
C122—C114—H114 | 107.5 | H32D—C321—H32E | 109.5 |
O102—C115—N116 | 119.0 (9) | C319—C321—H32F | 109.5 |
O102—C115—C114 | 121.1 (9) | H32D—C321—H32F | 109.5 |
N116—C115—C114 | 119.8 (7) | H32E—C321—H32F | 109.5 |
C114—C122—H12G | 109.5 | C317—C318—C319 | 129.9 (7) |
C114—C122—H12H | 109.5 | C317—C318—H318 | 115.1 |
H12G—C122—H12H | 109.5 | C319—C318—H318 | 115.1 |
C114—C122—H12I | 109.5 | C318—C317—N316 | 126.9 (7) |
H12G—C122—H12I | 109.5 | C318—C317—H317 | 116.5 |
H12H—C122—H12I | 109.5 | N316—C317—H317 | 116.5 |
C118—C119—C102 | 105.2 (7) | O301—C323—H32J | 109.5 |
C118—C119—C120 | 105.6 (7) | O301—C323—H32K | 109.5 |
C102—C119—C120 | 109.5 (7) | H32J—C323—H32K | 109.5 |
C118—C119—C121 | 110.4 (8) | O301—C323—H32L | 109.5 |
C102—C119—C121 | 110.1 (7) | H32J—C323—H32L | 109.5 |
C120—C119—C121 | 115.5 (8) | H32K—C323—H32L | 109.5 |
C119—C120—H12A | 109.5 | N401—C402—C403 | 106.0 (6) |
C119—C120—H12B | 109.5 | N401—C402—C419 | 123.2 (7) |
H12A—C120—H12B | 109.5 | C403—C402—C419 | 130.8 (6) |
C119—C120—H12C | 109.5 | C402—C403—C410 | 129.9 (6) |
H12A—C120—H12C | 109.5 | C402—C403—C409 | 107.6 (6) |
H12B—C120—H12C | 109.5 | C410—C403—C409 | 122.4 (6) |
C119—C121—H12D | 109.5 | C405—C404—C409 | 119.4 (7) |
C119—C121—H12E | 109.5 | C405—C404—H404 | 120.3 |
H12D—C121—H12E | 109.5 | C409—C404—H404 | 120.3 |
C119—C121—H12F | 109.5 | C404—C405—C406 | 121.0 (7) |
H12D—C121—H12F | 109.5 | C404—C405—H405 | 119.5 |
H12E—C121—H12F | 109.5 | C406—C405—H405 | 119.5 |
C117—C118—C119 | 128.9 (8) | O401—C406—C405 | 124.9 (7) |
C117—C118—H118 | 115.5 | O401—C406—C407 | 113.4 (7) |
C119—C118—H118 | 115.6 | C405—C406—C407 | 121.7 (7) |
C118—C117—N116 | 125.4 (9) | C408—C407—C406 | 116.5 (7) |
C118—C117—H117 | 117.3 | C408—C407—H407 | 121.8 |
N116—C117—H117 | 117.3 | C406—C407—H407 | 121.8 |
O101—C123—H12J | 109.5 | N401—C408—C407 | 129.0 (7) |
O101—C123—H12K | 109.5 | N401—C408—C409 | 108.5 (6) |
H12J—C123—H12K | 109.5 | C407—C408—C409 | 122.2 (7) |
O101—C123—H12L | 109.5 | C404—C409—C408 | 119.1 (7) |
H12J—C123—H12L | 109.5 | C404—C409—C403 | 134.8 (7) |
H12K—C123—H12L | 109.5 | C408—C409—C403 | 106.0 (6) |
N201—C202—C203 | 109.2 (6) | C411—C410—C403 | 141.6 (7) |
N201—C202—C219 | 122.9 (6) | C411—C410—H410 | 109.2 |
C203—C202—C219 | 127.8 (6) | C403—C410—H410 | 109.2 |
C202—C203—C209 | 105.9 (6) | C410—C411—N416 | 125.5 (6) |
C202—C203—C210 | 132.3 (7) | C410—C411—C412 | 118.2 (7) |
C209—C203—C210 | 121.7 (7) | N416—C411—C412 | 116.2 (6) |
C209—C204—C205 | 120.3 (8) | O403—C412—N413 | 121.1 (7) |
C209—C204—H204 | 119.9 | O403—C412—C411 | 121.8 (7) |
C205—C204—H204 | 119.9 | N413—C412—C411 | 117.1 (7) |
C204—C205—C206 | 119.9 (8) | N413—C414—C422 | 114.0 (6) |
C204—C205—H205 | 120.1 | N413—C414—C415 | 109.9 (5) |
C206—C205—H205 | 120.1 | C422—C414—C415 | 110.7 (6) |
O201—C206—C207 | 115.2 (7) | N413—C414—H414 | 107.3 |
O201—C206—C205 | 125.1 (7) | C422—C414—H414 | 107.3 |
C207—C206—C205 | 119.7 (8) | C415—C414—H414 | 107.3 |
C208—C207—C206 | 116.2 (7) | O402—C415—N416 | 122.6 (6) |
C208—C207—H207 | 121.9 | O402—C415—C414 | 119.6 (6) |
C206—C207—H207 | 121.9 | N416—C415—C414 | 117.8 (6) |
C207—C208—C209 | 125.9 (8) | C414—C422—H42G | 109.5 |
C207—C208—N201 | 128.4 (7) | C414—C422—H42H | 109.5 |
C209—C208—N201 | 105.7 (6) | H42G—C422—H42H | 109.5 |
C204—C209—C208 | 118.1 (7) | C414—C422—H42I | 109.5 |
C204—C209—C203 | 132.5 (7) | H42G—C422—H42I | 109.5 |
C208—C209—C203 | 109.4 (7) | H42H—C422—H42I | 109.5 |
C211—C210—C203 | 137.0 (7) | C418—C419—C421 | 113.1 (6) |
C211—C210—H210 | 111.5 | C418—C419—C402 | 104.2 (6) |
C203—C210—H210 | 111.5 | C421—C419—C402 | 110.9 (6) |
C210—C211—N216 | 128.6 (6) | C418—C419—C420 | 109.1 (6) |
C210—C211—C212 | 113.2 (7) | C421—C419—C420 | 108.1 (7) |
N216—C211—C212 | 118.1 (7) | C402—C419—C420 | 111.3 (6) |
O203—C212—N213 | 120.6 (7) | C419—C420—H42A | 109.5 |
O203—C212—C211 | 125.6 (7) | C419—C420—H42B | 109.5 |
N213—C212—C211 | 113.7 (7) | H42A—C420—H42B | 109.5 |
N213—C214—C222 | 109.5 (7) | C419—C420—H42C | 109.5 |
N213—C214—C215 | 106.8 (6) | H42A—C420—H42C | 109.5 |
C222—C214—C215 | 112.4 (7) | H42B—C420—H42C | 109.5 |
N213—C214—H214 | 109.4 | C419—C421—H42D | 109.5 |
C222—C214—H214 | 109.4 | C419—C421—H42E | 109.5 |
C215—C214—H214 | 109.4 | H42D—C421—H42E | 109.5 |
O202—C215—N216 | 120.5 (8) | C419—C421—H42F | 109.5 |
O202—C215—C214 | 120.9 (7) | H42D—C421—H42F | 109.5 |
N216—C215—C214 | 118.6 (7) | H42E—C421—H42F | 109.5 |
C214—C222—H22G | 109.5 | C417—C418—C419 | 131.5 (7) |
C214—C222—H22H | 109.5 | C417—C418—H418 | 114.3 |
H22G—C222—H22H | 109.5 | C419—C418—H418 | 114.3 |
C214—C222—H22I | 109.5 | C418—C417—N416 | 125.8 (6) |
H22G—C222—H22I | 109.5 | C418—C417—H417 | 117.1 |
H22H—C222—H22I | 109.5 | N416—C417—H417 | 117.1 |
C221—C219—C202 | 113.0 (6) | O401—C423—H42J | 109.5 |
C221—C219—C218 | 115.0 (6) | O401—C423—H42K | 109.5 |
C202—C219—C218 | 105.0 (5) | H42J—C423—H42K | 109.5 |
C221—C219—C220 | 108.1 (6) | O401—C423—H42L | 109.5 |
C202—C219—C220 | 111.0 (6) | H42J—C423—H42L | 109.5 |
C218—C219—C220 | 104.5 (6) | H42K—C423—H42L | 109.5 |
C219—C220—H22A | 109.5 | O501—C502—H50A | 109.5 |
C219—C220—H22B | 109.5 | O501—C502—H50B | 109.5 |
H22A—C220—H22B | 109.5 | H50A—C502—H50B | 109.5 |
C219—C220—H22C | 109.5 | O501—C502—H50C | 109.5 |
H22A—C220—H22C | 109.5 | H50A—C502—H50C | 109.5 |
H22B—C220—H22C | 109.5 | H50B—C502—H50C | 109.5 |
C219—C221—H22D | 109.5 | ||
C108—N101—C102—C103 | −1.3 (10) | C308—N301—C302—C303 | −2.4 (8) |
C108—N101—C102—C119 | −173.4 (8) | C308—N301—C302—C319 | 179.6 (6) |
N101—C102—C103—C110 | −178.1 (9) | N301—C302—C303—C309 | 2.6 (7) |
C119—C102—C103—C110 | −6.9 (15) | C319—C302—C303—C309 | −179.6 (6) |
N101—C102—C103—C109 | 4.2 (9) | N301—C302—C303—C310 | −174.9 (7) |
C119—C102—C103—C109 | 175.5 (8) | C319—C302—C303—C310 | 3.0 (13) |
C109—C104—C105—C106 | 0.3 (14) | C309—C304—C305—C306 | 6.3 (13) |
C104—C105—C106—C107 | −3.4 (14) | C304—C305—C306—C307 | −4.6 (13) |
C104—C105—C106—O101 | −178.1 (8) | C304—C305—C306—O301 | 178.2 (8) |
C123—O101—C106—C107 | 178.5 (8) | C323—O301—C306—C307 | 169.9 (8) |
C123—O101—C106—C105 | −6.4 (13) | C323—O301—C306—C305 | −12.7 (12) |
C105—C106—C107—C108 | 2.4 (14) | C305—C306—C307—C308 | 2.4 (13) |
O101—C106—C107—C108 | 177.3 (8) | O301—C306—C307—C308 | 179.8 (7) |
C102—N101—C108—C107 | −178.9 (9) | C306—C307—C308—C309 | −2.0 (12) |
C102—N101—C108—C109 | −2.2 (10) | C306—C307—C308—N301 | 178.3 (7) |
C106—C107—C108—N101 | 178.0 (9) | C302—N301—C308—C307 | −179.1 (8) |
C106—C107—C108—C109 | 1.8 (13) | C302—N301—C308—C309 | 1.1 (8) |
C105—C104—C109—C108 | 3.4 (13) | C307—C308—C309—C304 | 3.7 (11) |
C105—C104—C109—C103 | 174.8 (9) | N301—C308—C309—C304 | −176.5 (6) |
N101—C108—C109—C104 | 178.4 (8) | C307—C308—C309—C303 | −179.3 (7) |
C107—C108—C109—C104 | −4.5 (13) | N301—C308—C309—C303 | 0.5 (8) |
N101—C108—C109—C103 | 4.7 (9) | C305—C304—C309—C308 | −5.7 (11) |
C107—C108—C109—C103 | −178.3 (8) | C305—C304—C309—C303 | 178.2 (8) |
C102—C103—C109—C104 | −177.5 (10) | C302—C303—C309—C308 | −1.9 (8) |
C110—C103—C109—C104 | 4.5 (15) | C310—C303—C309—C308 | 176.0 (6) |
C102—C103—C109—C108 | −5.6 (9) | C302—C303—C309—C304 | 174.4 (8) |
C110—C103—C109—C108 | 176.5 (7) | C310—C303—C309—C304 | −7.7 (12) |
C102—C103—C110—C111 | −0.3 (19) | C302—C303—C310—C311 | −5.2 (15) |
C109—C103—C110—C111 | 177.1 (11) | C309—C303—C310—C311 | 177.7 (8) |
C103—C110—C111—N116 | −9 (2) | C303—C310—C311—N316 | −8.8 (15) |
C103—C110—C111—C112 | 176.1 (10) | C303—C310—C311—C312 | 176.3 (8) |
C115—N116—C111—C110 | 165.8 (11) | C315—N316—C311—C310 | 157.2 (8) |
C117—N116—C111—C110 | −37.8 (15) | C317—N316—C311—C310 | −39.5 (11) |
C115—N116—C111—C112 | −19.1 (16) | C315—N316—C311—C312 | −27.8 (9) |
C117—N116—C111—C112 | 137.3 (8) | C317—N316—C311—C312 | 135.5 (7) |
C114—N113—C112—O103 | −178.0 (7) | C314—N313—C312—O303 | −159.2 (7) |
C114—N113—C112—C111 | −2.8 (12) | C314—N313—C312—C311 | 18.4 (9) |
C110—C111—C112—O103 | 7.8 (13) | C310—C311—C312—O303 | 13.4 (11) |
N116—C111—C112—O103 | −167.7 (8) | N316—C311—C312—O303 | −162.2 (6) |
C110—C111—C112—N113 | −167.4 (8) | C310—C311—C312—N313 | −164.3 (7) |
N116—C111—C112—N113 | 17.1 (12) | N316—C311—C312—N313 | 20.1 (9) |
C112—N113—C114—C115 | −10.6 (12) | C312—N313—C314—C315 | −46.5 (8) |
C112—N113—C114—C122 | −135.7 (9) | C312—N313—C314—C322 | −170.0 (6) |
C111—N116—C115—O102 | −178.5 (12) | C311—N316—C315—O302 | 174.7 (7) |
C117—N116—C115—O102 | 24.4 (18) | C317—N316—C315—O302 | 11.8 (10) |
C111—N116—C115—C114 | 6.1 (19) | C311—N316—C315—C314 | −2.3 (10) |
C117—N116—C115—C114 | −150.9 (10) | C317—N316—C315—C314 | −165.3 (6) |
N113—C114—C115—O102 | −166.5 (12) | N313—C314—C315—O302 | −140.2 (7) |
C122—C114—C115—O102 | −43.7 (17) | C322—C314—C315—O302 | −17.7 (11) |
N113—C114—C115—N116 | 8.7 (16) | N313—C314—C315—N316 | 36.7 (8) |
C122—C114—C115—N116 | 131.6 (12) | C322—C314—C315—N316 | 159.2 (6) |
C103—C102—C119—C118 | 63.5 (11) | N301—C302—C319—C321 | 108.0 (7) |
N101—C102—C119—C118 | −126.4 (8) | C303—C302—C319—C321 | −69.7 (9) |
C103—C102—C119—C120 | 176.6 (9) | N301—C302—C319—C318 | −129.7 (6) |
N101—C102—C119—C120 | −13.3 (12) | C303—C302—C319—C318 | 52.6 (9) |
C103—C102—C119—C121 | −55.4 (12) | N301—C302—C319—C320 | −12.5 (9) |
N101—C102—C119—C121 | 114.7 (9) | C303—C302—C319—C320 | 169.8 (7) |
C102—C119—C118—C117 | −84.1 (11) | C302—C319—C318—C317 | −80.2 (10) |
C120—C119—C118—C117 | 160.1 (9) | C321—C319—C318—C317 | 41.2 (11) |
C121—C119—C118—C117 | 34.6 (12) | C320—C319—C318—C317 | 161.0 (8) |
C119—C118—C117—N116 | 2.8 (15) | C319—C318—C317—N316 | −0.4 (14) |
C115—N116—C117—C118 | −128.8 (12) | C315—N316—C317—C318 | −119.5 (9) |
C111—N116—C117—C118 | 73.0 (13) | C311—N316—C317—C318 | 76.8 (10) |
C208—N201—C202—C203 | −2.4 (9) | C408—N401—C402—C403 | 0.5 (8) |
C208—N201—C202—C219 | −179.6 (7) | C408—N401—C402—C419 | −178.8 (7) |
N201—C202—C203—C209 | 0.7 (8) | N401—C402—C403—C410 | 175.6 (7) |
C219—C202—C203—C209 | 177.8 (7) | C419—C402—C403—C410 | −5.2 (12) |
N201—C202—C203—C210 | −175.1 (7) | N401—C402—C403—C409 | −1.1 (7) |
C219—C202—C203—C210 | 1.9 (14) | C419—C402—C403—C409 | 178.2 (7) |
C209—C204—C205—C206 | −1.2 (11) | C409—C404—C405—C406 | 3.4 (12) |
C223—O201—C206—C207 | −176.8 (7) | C423—O401—C406—C405 | 2.0 (12) |
C223—O201—C206—C205 | 5.3 (12) | C423—O401—C406—C407 | −177.5 (7) |
C204—C205—C206—O201 | 178.6 (7) | C404—C405—C406—O401 | 177.8 (7) |
C204—C205—C206—C207 | 0.8 (11) | C404—C405—C406—C407 | −2.8 (12) |
O201—C206—C207—C208 | −177.5 (7) | O401—C406—C407—C408 | −179.1 (7) |
C205—C206—C207—C208 | 0.5 (11) | C405—C406—C407—C408 | 1.4 (11) |
C206—C207—C208—C209 | −1.5 (13) | C402—N401—C408—C407 | 175.1 (8) |
C206—C207—C208—N201 | −180.0 (7) | C402—N401—C408—C409 | 0.2 (8) |
C202—N201—C208—C207 | −178.3 (8) | C406—C407—C408—N401 | −175.1 (7) |
C202—N201—C208—C209 | 3.0 (9) | C406—C407—C408—C409 | −0.8 (11) |
C205—C204—C209—C208 | 0.3 (12) | C405—C404—C409—C408 | −2.8 (11) |
C205—C204—C209—C203 | −176.6 (8) | C405—C404—C409—C403 | 174.1 (8) |
C207—C208—C209—C204 | 1.1 (13) | N401—C408—C409—C404 | 176.9 (6) |
N201—C208—C209—C204 | 179.8 (7) | C407—C408—C409—C404 | 1.5 (11) |
C207—C208—C209—C203 | 178.7 (8) | N401—C408—C409—C403 | −0.8 (8) |
N201—C208—C209—C203 | −2.5 (9) | C407—C408—C409—C403 | −176.2 (7) |
C202—C203—C209—C204 | 178.3 (9) | C402—C403—C409—C404 | −176.0 (8) |
C210—C203—C209—C204 | −5.2 (13) | C410—C403—C409—C404 | 7.1 (13) |
C202—C203—C209—C208 | 1.2 (9) | C402—C403—C409—C408 | 1.2 (8) |
C210—C203—C209—C208 | 177.6 (7) | C410—C403—C409—C408 | −175.7 (6) |
C202—C203—C210—C211 | −14.4 (15) | C402—C403—C410—C411 | 12.0 (15) |
C209—C203—C210—C211 | 170.3 (8) | C409—C403—C410—C411 | −171.8 (9) |
C203—C210—C211—N216 | −4.8 (14) | C403—C410—C411—N416 | 8.4 (15) |
C203—C210—C211—C212 | 178.1 (8) | C403—C410—C411—C412 | −172.1 (9) |
C215—N216—C211—C210 | 157.9 (7) | C415—N416—C411—C410 | −160.0 (7) |
C217—N216—C211—C210 | −36.4 (11) | C417—N416—C411—C410 | 33.6 (10) |
C215—N216—C211—C212 | −25.1 (10) | C415—N416—C411—C412 | 20.5 (9) |
C217—N216—C211—C212 | 140.6 (6) | C417—N416—C411—C412 | −145.9 (7) |
C214—N213—C212—O203 | −156.9 (7) | C414—N413—C412—O403 | 168.7 (6) |
C214—N213—C212—C211 | 20.7 (11) | C414—N413—C412—C411 | −11.7 (10) |
C210—C211—C212—O203 | 12.6 (11) | C410—C411—C412—O403 | −17.6 (11) |
N216—C211—C212—O203 | −164.8 (7) | N416—C411—C412—O403 | 161.9 (6) |
C210—C211—C212—N213 | −164.8 (7) | C410—C411—C412—N413 | 162.8 (7) |
N216—C211—C212—N213 | 17.7 (10) | N416—C411—C412—N413 | −17.7 (9) |
C212—N213—C214—C222 | −169.4 (8) | C412—N413—C414—C422 | −89.6 (8) |
C212—N213—C214—C215 | −47.4 (10) | C412—N413—C414—C415 | 35.3 (9) |
C211—N216—C215—O202 | 173.5 (7) | C411—N416—C415—O402 | −175.1 (6) |
C217—N216—C215—O202 | 7.5 (11) | C417—N416—C415—O402 | −7.8 (10) |
C211—N216—C215—C214 | −5.7 (11) | C411—N416—C415—C414 | 5.0 (10) |
C217—N216—C215—C214 | −171.6 (6) | C417—N416—C415—C414 | 172.2 (6) |
N213—C214—C215—O202 | −140.6 (7) | N413—C414—C415—O402 | 149.2 (6) |
C222—C214—C215—O202 | −20.5 (12) | C422—C414—C415—O402 | −84.0 (9) |
N213—C214—C215—N216 | 38.6 (10) | N413—C414—C415—N416 | −30.8 (9) |
C222—C214—C215—N216 | 158.7 (8) | C422—C414—C415—N416 | 95.9 (7) |
N201—C202—C219—C221 | 113.4 (8) | N401—C402—C419—C418 | 124.4 (7) |
C203—C202—C219—C221 | −63.3 (10) | C403—C402—C419—C418 | −54.7 (9) |
N201—C202—C219—C218 | −120.5 (7) | N401—C402—C419—C421 | −113.5 (8) |
C203—C202—C219—C218 | 62.8 (10) | C403—C402—C419—C421 | 67.4 (10) |
N201—C202—C219—C220 | −8.3 (10) | N401—C402—C419—C420 | 7.0 (10) |
C203—C202—C219—C220 | 175.0 (7) | C403—C402—C419—C420 | −172.1 (7) |
C221—C219—C218—C217 | 40.5 (9) | C421—C419—C418—C417 | −38.3 (11) |
C202—C219—C218—C217 | −84.3 (8) | C402—C419—C418—C417 | 82.3 (9) |
C220—C219—C218—C217 | 158.9 (6) | C420—C419—C418—C417 | −158.7 (8) |
C219—C218—C217—N216 | −1.4 (10) | C419—C418—C417—N416 | −3.3 (13) |
C215—N216—C217—C218 | −119.5 (8) | C415—N416—C417—C418 | 121.2 (8) |
C211—N216—C217—C218 | 74.5 (9) | C411—N416—C417—C418 | −71.4 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N313—H313···O203i | 0.86 | 2.01 | 2.847 (6) | 165 |
N301—H301···O302ii | 0.86 | 2.13 | 2.919 (6) | 153 |
N201—H201···O202iii | 0.86 | 2.20 | 2.936 (6) | 144 |
N213—H213···O303ii | 0.86 | 2.03 | 2.834 (6) | 155 |
N113—H113···O403 | 0.86 | 2.02 | 2.861 (6) | 167 |
N413—H413···O103 | 0.86 | 2.08 | 2.900 (6) | 158 |
N401—H401···O402iv | 0.86 | 2.07 | 2.859 (6) | 152 |
N101—H101···O102v | 0.86 | 2.12 | 2.928 (6) | 156 |
O501—H501···O103i | 0.82 | 1.87 | 2.677 (6) | 167 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) −x+2, y+1/2, −z; (iv) −x+1, y+1/2, −z+2; (v) −x+2, y−1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H21N3O3·0.25CH4O |
Mr | 359.41 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 15.222 (2), 16.848 (2), 15.930 (2) |
β (°) | 114.27 (1) |
V (Å3) | 3724.3 (8) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.09 |
Crystal size (mm) | 0.6 × 0.3 × 0.3 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14273, 13028, 4745 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.064, 0.209, 0.83 |
No. of reflections | 13028 |
No. of parameters | 973 |
No. of restraints | 43 |
H-atom treatment | H-atom parameters constrained |
(Δ/σ)max | 0.121 |
Δρmax, Δρmin (e Å−3) | 0.52, −0.31 |
Absolute structure | (Flack, 1983), 6232 Friedel pairs |
Absolute structure parameter | 2.7 (19) |
Computer programs: CAD-4-PC Software (Enraf-Nonius, 1992), CELLDIM in CAD-4-PC Software, XCAD4 (McArdle & Higgins, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEX (McArdle, 1995), OSCAIL (McArdle, 1993).
C102—C119—C118—C117 | −84.1 (11) | C302—C319—C318—C317 | −80.2 (10) |
C111—N116—C117—C118 | 73.0 (13) | C311—N316—C317—C318 | 76.8 (10) |
C202—C219—C218—C217 | −84.3 (8) | C402—C419—C418—C417 | 82.3 (9) |
C211—N216—C217—C218 | 74.5 (9) | C411—N416—C417—C418 | −71.4 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N313—H313···O203i | 0.86 | 2.007 | 2.847 (6) | 165 |
N301—H301···O302ii | 0.86 | 2.128 | 2.919 (6) | 153 |
N201—H201···O202iii | 0.86 | 2.197 | 2.936 (6) | 144 |
N213—H213···O303ii | 0.86 | 2.030 | 2.834 (6) | 155 |
N113—H113···O403 | 0.86 | 2.017 | 2.861 (6) | 167 |
N413—H413···O103 | 0.86 | 2.083 | 2.900 (6) | 158 |
N401—H401···O402iv | 0.86 | 2.074 | 2.859 (6) | 152 |
N101—H101···O102v | 0.86 | 2.121 | 2.928 (6) | 156 |
O501—H501···O103i | 0.82 | 1.872 | 2.677 (6) | 167 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+1, y−1/2, −z+1; (iii) −x+2, y+1/2, −z; (iv) −x+1, y+1/2, −z+2; (v) −x+2, y−1/2, −z+1. |
Aspergillus ochraceus is known to produce a number of alkaloids constructed from various amino acids, such as Phe, Ala, Trp, and Pro (Merve et al., 1965; Rahbaek & Breinholt, 1999; Rahbaek et al., 1999). Cycloechinulin (I) was first isolated in 1992 in minute quantities, 1.1 mg, from the sclerotia of A. ochraceus by De Guzman et al. (1992). The Trp-Ala-derived structure was proposed on the basis of spectroscopic properties, but has not been established by X-ray diffraction. Cycloechinulin (I) is structurally related to the pentacyclic Trp-Pro-derived alkaloid (II) which was isolated from A. ustus by Steyn in 1973, and, more remotely, to those of the echinulin series of compounds, e.g. neoechinulin from A. amstelodami (Barbetta et al., 1969; Dossena et al., 1974; Quilico & Panizzi, 1943; Steyn, 1971; Yamamoto & Arai, 1986). Cycloechinulin (I) has been shown to excert moderate insecticidal activity against the lepidopteran crop pest Helicoverpa zea (De Guzman et al., 1992). Substantial amounts of cycloechinulin (I) has now been isolated from the mycelial mat of A. ochraceus and its structure confirmed by X-ray diffraction analysis.
The title compound crystallizes in the monoclinic non-centrosymmetric space group P21 with four molecules in the asymmetric unit. The crystal structure also includes one methanol molecule. The four independent molecules are shown in Figs. 1–4. The conformation of molecules 1–3 are almost identical, while molecule 4 is found in a different conformation in the eight-membered dihydroazocin moiety and six-membered 2,5-diketopiperazin part of the molecule (see Table 1 and Figs. 5–8). The indole part of all four molecules are planar and the atoms CX23, OX01, CX10 and CX19 (X = 1–4), are also in the same plane [largest deviation -0.138 (10) Å for atom C419]. A selection of bond lengths shows that these are all within the normal range of such bonds (Allen et al., 1986). The mean value for the C═ O bonds is 1.232 (15) Å, while the CX02═CX03 bonds have an average bond length of 1.38 (2) Å. The mean value of the CX10═CX11 and CX18═CX17 bonds is 1.32 (3) Å. The molecules are packed in the crystal through a series of intermolecular hydrogen bonds which also involve the methanol molecule (see Table 2).