Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768110040243/so5040sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401asup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401asup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401a-roomsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401bsup5.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50402asup6.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50402bsup7.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50409asup8.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50409bsup9.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50409b-roomsup10.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so504010asup11.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so504010bsup12.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so504010b-roomsup13.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S0108768110040243/so5040sup14.pdf |
CCDC references: 755931; 755932; 755933; 755934; 755935; 755936; 755937; 755938; 810883; 810884; 810885
Data collection: COLLECT (Hooft, 1998) and DENZO (Otwinowski & Minor, 1997) for (1a), 1a-room, (1b), (2a), (2b), (9a), (9b), (10a), (10b); Enraf-Nonius CAD4 Version 5.0 for 9b-room, 10b-room. Cell refinement: COLLECT and DENZO for (1a), 1a-room, (1b), (2a), (2b), (9a), (9b), (10a), (10b); Enraf-Nonius CAD4 Version 5.0 for 9b-room, 10b-room. Data reduction: COLLECT and DENZO for (1a), 1a-room, (1b), (2a), (2b), (9a), (9b), (10a), (10b); JANA2006, (Petricek,2006) for 9b-room, 10b-room. Program(s) used to solve structure: SIR92 (Altomare et al., 1994) for (1a), 1a-room, (1b), (2a), (2b), (9a), (9b), (10a), (10b); SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79) for 9b-room, 10b-room. For all structures, program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
2(C15H18N4O4)·H2O | F(000) = 1144 |
Mr = 534.64 | Dx = 1.269 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2yb | Cell parameters from 25066 reflections |
a = 8.4202 (2) Å | θ = 1–25.0° |
b = 24.7788 (4) Å | µ = 0.09 mm−1 |
c = 13.4204 (3) Å | T = 150 K |
β = 91.6730 (11)° | Plate, colourless |
V = 2798.87 (10) Å3 | 0.3 × 0.25 × 0.25 mm |
Z = 4 |
Nonius KappaCCD area detector diffractometer | 8038 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.060 |
Graphite monochromator | θmax = 25.0°, θmin = 1.5° |
Detector resolution: 9.091 pixels mm-1 | h = −10→9 |
φ and ω scans to fill the Ewald sphere | k = −29→27 |
31329 measured reflections | l = −15→15 |
9713 independent reflections |
Refinement on F2 | Hydrogen site location: difference Fourier map |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.054 | w = 1/[σ2(Fo2) + (0.077P)2 + 0.7105P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.137 | (Δ/σ)max = 0.001 |
S = 1.04 | Δρmax = 0.32 e Å−3 |
9713 reflections | Δρmin = −0.23 e Å−3 |
736 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.0273 (18) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.2 (10) |
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 | ||
N11 | 0.6263 (3) | 0.26408 (10) | 0.41438 (18) | 0.0328 (6) | |
C12 | 0.7683 (4) | 0.25815 (12) | 0.3764 (2) | 0.0310 (7) | |
O12 | 0.8290 (3) | 0.21328 (8) | 0.35927 (17) | 0.0396 (5) | |
C13 | 0.8666 (3) | 0.30768 (11) | 0.3543 (2) | 0.0332 (7) | |
H13 | 0.9055 | 0.3037 | 0.2866 | 0.040* | |
N14 | 0.7782 (3) | 0.35798 (10) | 0.35732 (19) | 0.0317 (6) | |
C15 | 0.6330 (4) | 0.36411 (12) | 0.3895 (2) | 0.0317 (7) | |
O15 | 0.5649 (3) | 0.40899 (9) | 0.39059 (17) | 0.0433 (6) | |
C16 | 0.5454 (3) | 0.31581 (12) | 0.4283 (2) | 0.0330 (7) | |
H16 | 0.4442 | 0.3138 | 0.3905 | 0.040* | |
C17 | 0.5055 (4) | 0.32292 (13) | 0.5372 (3) | 0.0438 (8) | |
H17A | 0.4448 | 0.3558 | 0.5450 | 0.053* | |
H17B | 0.6029 | 0.3262 | 0.5771 | 0.053* | |
C18 | 0.4099 (4) | 0.27523 (14) | 0.5742 (3) | 0.0467 (9) | |
H18A | 0.3949 | 0.2790 | 0.6452 | 0.056* | |
H18B | 0.3059 | 0.2752 | 0.5411 | 0.056* | |
C19 | 0.4927 (4) | 0.22198 (13) | 0.5542 (2) | 0.0393 (7) | |
H19A | 0.5896 | 0.2197 | 0.5949 | 0.047* | |
H19B | 0.4242 | 0.1923 | 0.5724 | 0.047* | |
C110 | 0.5323 (4) | 0.21735 (13) | 0.4450 (3) | 0.0416 (8) | |
H11A | 0.5919 | 0.1845 | 0.4343 | 0.050* | |
H11B | 0.4348 | 0.2155 | 0.4048 | 0.050* | |
C111 | 1.0139 (3) | 0.30983 (13) | 0.4264 (3) | 0.0390 (7) | |
H11C | 1.0784 | 0.2780 | 0.4162 | 0.047* | |
H11D | 1.0774 | 0.3411 | 0.4103 | 0.047* | |
C112 | 0.9711 (4) | 0.31271 (13) | 0.5343 (2) | 0.0379 (7) | |
C113 | 0.9509 (4) | 0.36186 (14) | 0.5808 (3) | 0.0504 (9) | |
H113 | 0.9652 | 0.3936 | 0.5453 | 0.060* | |
C114 | 0.9096 (6) | 0.36432 (16) | 0.6797 (3) | 0.0668 (12) | |
H114 | 0.8968 | 0.3977 | 0.7100 | 0.080* | |
C115 | 0.8870 (6) | 0.31763 (16) | 0.7338 (3) | 0.0663 (12) | |
H115 | 0.8596 | 0.3194 | 0.8003 | 0.080* | |
C116 | 0.9057 (5) | 0.26840 (14) | 0.6876 (3) | 0.0551 (10) | |
H116 | 0.8890 | 0.2367 | 0.7229 | 0.066* | |
C117 | 0.9491 (4) | 0.26592 (13) | 0.5895 (2) | 0.0426 (8) | |
H117 | 0.9639 | 0.2325 | 0.5597 | 0.051* | |
N21 | 0.7543 (3) | 0.05767 (10) | 0.62446 (19) | 0.0332 (6) | |
C22 | 0.8586 (4) | 0.09464 (12) | 0.6568 (2) | 0.0343 (7) | |
O22 | 0.8274 (3) | 0.14345 (9) | 0.65905 (19) | 0.0484 (6) | |
C23 | 1.0233 (4) | 0.07749 (12) | 0.6882 (2) | 0.0352 (7) | |
H23 | 1.0459 | 0.0932 | 0.7541 | 0.042* | |
N24 | 1.0421 (3) | 0.01897 (10) | 0.69821 (19) | 0.0342 (6) | |
C25 | 0.9404 (4) | −0.01779 (12) | 0.6630 (2) | 0.0326 (7) | |
O25 | 0.9698 (3) | −0.06727 (8) | 0.67021 (17) | 0.0410 (5) | |
C26 | 0.7863 (4) | −0.00055 (11) | 0.6152 (2) | 0.0313 (7) | |
H26 | 0.7014 | −0.0198 | 0.6487 | 0.038* | |
C27 | 0.7778 (4) | −0.01700 (13) | 0.5046 (2) | 0.0360 (7) | |
H27A | 0.8675 | −0.0016 | 0.4709 | 0.043* | |
H27B | 0.7849 | −0.0560 | 0.4995 | 0.043* | |
C28 | 0.6241 (4) | 0.00206 (13) | 0.4533 (3) | 0.0425 (8) | |
H28A | 0.5357 | −0.0184 | 0.4787 | 0.051* | |
H28B | 0.6289 | −0.0048 | 0.3823 | 0.051* | |
C29 | 0.5956 (4) | 0.06199 (14) | 0.4703 (3) | 0.0427 (8) | |
H29A | 0.6766 | 0.0829 | 0.4377 | 0.051* | |
H29B | 0.4929 | 0.0722 | 0.4416 | 0.051* | |
C210 | 0.6006 (4) | 0.07401 (13) | 0.5809 (3) | 0.0401 (8) | |
H21A | 0.5846 | 0.1123 | 0.5915 | 0.048* | |
H21B | 0.5161 | 0.0546 | 0.6129 | 0.048* | |
C211 | 1.1458 (4) | 0.10086 (13) | 0.6171 (2) | 0.0372 (7) | |
H21C | 1.1351 | 0.1398 | 0.6155 | 0.045* | |
H21D | 1.2518 | 0.0925 | 0.6428 | 0.045* | |
C212 | 1.1267 (4) | 0.07916 (12) | 0.5124 (2) | 0.0342 (7) | |
C213 | 1.0324 (4) | 0.10571 (13) | 0.4414 (2) | 0.0399 (8) | |
H213 | 0.9834 | 0.1379 | 0.4583 | 0.048* | |
C214 | 1.0098 (5) | 0.08536 (15) | 0.3467 (3) | 0.0518 (9) | |
H214 | 0.9455 | 0.1036 | 0.3003 | 0.062* | |
C215 | 1.0833 (5) | 0.03748 (16) | 0.3208 (3) | 0.0521 (10) | |
H215 | 1.0688 | 0.0236 | 0.2568 | 0.063* | |
C216 | 1.1777 (4) | 0.01056 (15) | 0.3898 (3) | 0.0477 (9) | |
H216 | 1.2278 | −0.0214 | 0.3723 | 0.057* | |
C217 | 1.1983 (4) | 0.03100 (13) | 0.4855 (2) | 0.0382 (7) | |
H217 | 1.2607 | 0.0123 | 0.5322 | 0.046* | |
N31 | 0.7141 (3) | 0.14447 (10) | 0.12665 (19) | 0.0346 (6) | |
C32 | 0.6162 (4) | 0.10629 (12) | 0.1599 (2) | 0.0347 (7) | |
O32 | 0.6514 (3) | 0.05793 (9) | 0.1602 (2) | 0.0494 (6) | |
C33 | 0.4556 (4) | 0.12232 (12) | 0.1940 (2) | 0.0363 (7) | |
H33 | 0.4420 | 0.1056 | 0.2594 | 0.044* | |
N34 | 0.4338 (3) | 0.18010 (10) | 0.20695 (19) | 0.0344 (6) | |
C35 | 0.5299 (4) | 0.21839 (13) | 0.1754 (2) | 0.0340 (7) | |
O35 | 0.5002 (3) | 0.26704 (8) | 0.18591 (17) | 0.0431 (6) | |
C36 | 0.6795 (4) | 0.20251 (12) | 0.1239 (2) | 0.0331 (7) | |
H36 | 0.7682 | 0.2210 | 0.1584 | 0.040* | |
C37 | 0.6745 (4) | 0.22241 (13) | 0.0153 (2) | 0.0382 (7) | |
H37A | 0.5817 | 0.2075 | −0.0192 | 0.046* | |
H37B | 0.6646 | 0.2614 | 0.0146 | 0.046* | |
C38 | 0.8220 (4) | 0.20624 (15) | −0.0391 (3) | 0.0477 (9) | |
H38A | 0.9127 | 0.2258 | −0.0114 | 0.057* | |
H38B | 0.8093 | 0.2160 | −0.1089 | 0.057* | |
C39 | 0.8533 (4) | 0.14563 (14) | −0.0306 (3) | 0.0458 (8) | |
H39A | 0.7689 | 0.1259 | −0.0651 | 0.055* | |
H39B | 0.9528 | 0.1368 | −0.0614 | 0.055* | |
C310 | 0.8611 (4) | 0.12945 (14) | 0.0789 (3) | 0.0449 (8) | |
H31A | 0.8771 | 0.0908 | 0.0845 | 0.054* | |
H31B | 0.9503 | 0.1473 | 0.1123 | 0.054* | |
C311 | 0.3264 (4) | 0.09830 (13) | 0.1230 (2) | 0.0382 (7) | |
H31C | 0.3389 | 0.0594 | 0.1209 | 0.046* | |
H31D | 0.2227 | 0.1060 | 0.1493 | 0.046* | |
C312 | 0.3328 (4) | 0.12018 (13) | 0.0188 (2) | 0.0369 (7) | |
C313 | 0.2558 (4) | 0.16822 (13) | −0.0067 (3) | 0.0402 (8) | |
H313 | 0.1980 | 0.1864 | 0.0409 | 0.048* | |
C314 | 0.2643 (4) | 0.18934 (15) | −0.1020 (3) | 0.0484 (9) | |
H314 | 0.2106 | 0.2210 | −0.1187 | 0.058* | |
C315 | 0.3535 (5) | 0.16292 (16) | −0.1724 (3) | 0.0552 (10) | |
H315 | 0.3601 | 0.1771 | −0.2363 | 0.066* | |
C316 | 0.4319 (5) | 0.11594 (16) | −0.1484 (3) | 0.0560 (10) | |
H316 | 0.4930 | 0.0987 | −0.1954 | 0.067* | |
C317 | 0.4198 (4) | 0.09419 (14) | −0.0537 (3) | 0.0451 (8) | |
H317 | 0.4706 | 0.0618 | −0.0384 | 0.054* | |
N41 | 0.8721 (3) | −0.05542 (9) | −0.09715 (18) | 0.0316 (6) | |
C42 | 0.7229 (4) | −0.05342 (12) | −0.1329 (2) | 0.0321 (7) | |
O42 | 0.6501 (3) | −0.01000 (8) | −0.14541 (17) | 0.0391 (5) | |
C43 | 0.6360 (3) | −0.10471 (11) | −0.1565 (2) | 0.0316 (7) | |
H43 | 0.5869 | −0.1009 | −0.2233 | 0.038* | |
N44 | 0.7371 (3) | −0.15279 (10) | −0.15730 (19) | 0.0329 (6) | |
C45 | 0.8872 (4) | −0.15539 (12) | −0.1268 (2) | 0.0333 (7) | |
O45 | 0.9653 (3) | −0.19805 (8) | −0.12731 (17) | 0.0433 (6) | |
C46 | 0.9698 (3) | −0.10473 (12) | −0.0897 (2) | 0.0330 (7) | |
H46 | 1.0615 | −0.0991 | −0.1318 | 0.040* | |
C47 | 1.0348 (4) | −0.11212 (13) | 0.0169 (2) | 0.0400 (7) | |
H47A | 0.9478 | −0.1203 | 0.0603 | 0.048* | |
H47B | 1.1078 | −0.1424 | 0.0191 | 0.048* | |
C48 | 1.1201 (4) | −0.06187 (15) | 0.0543 (3) | 0.0458 (8) | |
H48A | 1.1517 | −0.0666 | 0.1239 | 0.055* | |
H48B | 1.2154 | −0.0564 | 0.0167 | 0.055* | |
C49 | 1.0142 (4) | −0.01272 (13) | 0.0437 (2) | 0.0396 (7) | |
H49A | 0.9245 | −0.0165 | 0.0869 | 0.048* | |
H49B | 1.0733 | 0.0192 | 0.0642 | 0.048* | |
C410 | 0.9547 (4) | −0.00611 (12) | −0.0625 (3) | 0.0398 (7) | |
H41A | 0.8824 | 0.0243 | −0.0670 | 0.048* | |
H41B | 1.0435 | 0.0012 | −0.1049 | 0.048* | |
C411 | 0.5012 (4) | −0.11192 (14) | −0.0822 (2) | 0.0389 (7) | |
H41C | 0.4272 | −0.0821 | −0.0900 | 0.047* | |
H41D | 0.4439 | −0.1449 | −0.0983 | 0.047* | |
C412 | 0.5592 (4) | −0.11436 (13) | 0.0244 (2) | 0.0370 (7) | |
C413 | 0.5732 (4) | −0.06755 (13) | 0.0821 (3) | 0.0433 (8) | |
H413 | 0.5421 | −0.0346 | 0.0545 | 0.052* | |
C414 | 0.6318 (5) | −0.06906 (14) | 0.1786 (3) | 0.0518 (10) | |
H414 | 0.6409 | −0.0374 | 0.2154 | 0.062* | |
C415 | 0.6774 (5) | −0.11759 (15) | 0.2210 (3) | 0.0561 (10) | |
H415 | 0.7155 | −0.1189 | 0.2867 | 0.067* | |
C416 | 0.6659 (6) | −0.16415 (15) | 0.1649 (3) | 0.0585 (11) | |
H416 | 0.6986 | −0.1969 | 0.1926 | 0.070* | |
C417 | 0.6065 (5) | −0.16256 (13) | 0.0688 (3) | 0.0455 (8) | |
H417 | 0.5977 | −0.1945 | 0.0326 | 0.055* | |
O1W | 0.1138 (3) | 0.21200 (10) | 0.2438 (2) | 0.0475 (6) | |
O2W | 1.3586 (3) | −0.01206 (11) | 0.7449 (2) | 0.0517 (7) | |
H14 | 0.835 (5) | 0.3870 (18) | 0.336 (3) | 0.062 (12)* | |
H24 | 1.156 (4) | 0.0089 (12) | 0.717 (2) | 0.031 (8)* | |
H34 | 0.324 (4) | 0.1929 (13) | 0.232 (2) | 0.037 (8)* | |
H44 | 0.677 (4) | −0.1838 (16) | −0.162 (3) | 0.044 (9)* | |
H11W | 0.025 (5) | 0.2084 (17) | 0.286 (3) | 0.066 (12)* | |
H12W | 0.092 (5) | 0.242 (2) | 0.199 (4) | 0.076 (13)* | |
H21W | 1.474 (5) | −0.0106 (16) | 0.769 (3) | 0.063 (11)* | |
H22W | 1.383 (4) | −0.0330 (16) | 0.706 (3) | 0.041 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0381 (14) | 0.0275 (13) | 0.0331 (14) | 0.0009 (11) | 0.0061 (11) | −0.0001 (11) |
C12 | 0.0410 (17) | 0.0277 (16) | 0.0242 (15) | 0.0022 (13) | 0.0000 (12) | 0.0001 (13) |
O12 | 0.0519 (13) | 0.0252 (12) | 0.0423 (13) | 0.0072 (10) | 0.0123 (10) | 0.0002 (9) |
C13 | 0.0395 (16) | 0.0254 (16) | 0.0351 (17) | 0.0025 (13) | 0.0066 (13) | 0.0041 (13) |
N14 | 0.0397 (15) | 0.0220 (13) | 0.0336 (14) | 0.0003 (11) | 0.0041 (11) | 0.0039 (11) |
C15 | 0.0414 (18) | 0.0265 (16) | 0.0271 (16) | 0.0067 (13) | −0.0038 (13) | 0.0060 (12) |
O15 | 0.0547 (13) | 0.0335 (13) | 0.0418 (14) | 0.0137 (11) | 0.0032 (10) | 0.0057 (10) |
C16 | 0.0329 (15) | 0.0324 (16) | 0.0336 (17) | 0.0047 (13) | 0.0022 (12) | 0.0009 (13) |
C17 | 0.054 (2) | 0.0356 (18) | 0.042 (2) | 0.0099 (15) | 0.0158 (16) | −0.0002 (14) |
C18 | 0.051 (2) | 0.045 (2) | 0.045 (2) | 0.0091 (16) | 0.0189 (16) | 0.0046 (16) |
C19 | 0.0440 (18) | 0.0363 (18) | 0.0381 (19) | −0.0009 (14) | 0.0077 (14) | 0.0022 (14) |
C110 | 0.0482 (19) | 0.0356 (18) | 0.0414 (19) | −0.0080 (15) | 0.0089 (15) | −0.0024 (15) |
C111 | 0.0341 (16) | 0.0305 (17) | 0.052 (2) | 0.0040 (13) | 0.0042 (14) | 0.0057 (15) |
C112 | 0.0381 (16) | 0.0330 (17) | 0.0421 (19) | −0.0014 (14) | −0.0081 (13) | 0.0014 (15) |
C113 | 0.071 (2) | 0.0338 (19) | 0.046 (2) | −0.0078 (17) | −0.0122 (18) | 0.0038 (16) |
C114 | 0.122 (4) | 0.036 (2) | 0.041 (2) | −0.006 (2) | −0.010 (2) | −0.0109 (17) |
C115 | 0.119 (4) | 0.045 (2) | 0.034 (2) | −0.006 (2) | −0.013 (2) | −0.0031 (17) |
C116 | 0.093 (3) | 0.033 (2) | 0.038 (2) | −0.0109 (18) | −0.0127 (19) | 0.0029 (15) |
C117 | 0.059 (2) | 0.0296 (17) | 0.039 (2) | 0.0015 (15) | −0.0085 (15) | 0.0000 (14) |
N21 | 0.0359 (13) | 0.0282 (14) | 0.0353 (15) | 0.0047 (11) | −0.0003 (11) | −0.0017 (11) |
C22 | 0.0442 (18) | 0.0241 (17) | 0.0347 (17) | 0.0020 (13) | 0.0021 (14) | −0.0047 (13) |
O22 | 0.0514 (14) | 0.0256 (13) | 0.0679 (17) | 0.0047 (10) | −0.0014 (12) | −0.0053 (11) |
C23 | 0.0453 (18) | 0.0286 (16) | 0.0315 (17) | −0.0019 (13) | −0.0018 (13) | −0.0077 (13) |
N24 | 0.0424 (15) | 0.0271 (14) | 0.0331 (15) | 0.0052 (12) | 0.0003 (12) | 0.0042 (11) |
C25 | 0.0416 (17) | 0.0283 (17) | 0.0281 (16) | 0.0019 (14) | 0.0051 (13) | −0.0034 (13) |
O25 | 0.0558 (14) | 0.0248 (12) | 0.0427 (14) | 0.0062 (10) | 0.0031 (10) | 0.0037 (9) |
C26 | 0.0401 (16) | 0.0201 (15) | 0.0340 (17) | 0.0027 (12) | 0.0057 (13) | −0.0004 (12) |
C27 | 0.0381 (17) | 0.0385 (18) | 0.0316 (17) | −0.0030 (14) | 0.0022 (13) | −0.0061 (14) |
C28 | 0.0409 (18) | 0.049 (2) | 0.0378 (19) | −0.0058 (15) | −0.0003 (14) | −0.0008 (15) |
C29 | 0.0357 (17) | 0.044 (2) | 0.048 (2) | −0.0039 (14) | −0.0012 (15) | 0.0110 (16) |
C210 | 0.0376 (17) | 0.0290 (17) | 0.054 (2) | 0.0050 (13) | −0.0002 (15) | 0.0042 (14) |
C211 | 0.0383 (17) | 0.0298 (17) | 0.0431 (19) | 0.0000 (13) | −0.0048 (14) | −0.0031 (14) |
C212 | 0.0359 (16) | 0.0327 (17) | 0.0341 (17) | −0.0082 (13) | 0.0017 (13) | 0.0006 (13) |
C213 | 0.0492 (19) | 0.0329 (17) | 0.0377 (19) | −0.0047 (14) | 0.0024 (15) | 0.0099 (14) |
C214 | 0.065 (2) | 0.049 (2) | 0.042 (2) | −0.0084 (18) | −0.0021 (17) | 0.0171 (17) |
C215 | 0.068 (2) | 0.058 (2) | 0.0313 (19) | −0.0199 (19) | 0.0087 (17) | −0.0038 (17) |
C216 | 0.051 (2) | 0.047 (2) | 0.046 (2) | −0.0070 (16) | 0.0137 (17) | −0.0113 (17) |
C217 | 0.0325 (16) | 0.0402 (19) | 0.042 (2) | −0.0019 (14) | 0.0033 (14) | 0.0013 (15) |
N31 | 0.0365 (14) | 0.0270 (14) | 0.0404 (16) | 0.0046 (11) | 0.0012 (11) | −0.0020 (11) |
C32 | 0.0409 (17) | 0.0276 (18) | 0.0352 (18) | −0.0009 (14) | −0.0057 (13) | 0.0014 (13) |
O32 | 0.0543 (14) | 0.0278 (13) | 0.0658 (17) | 0.0050 (10) | −0.0007 (12) | 0.0034 (11) |
C33 | 0.0464 (18) | 0.0318 (17) | 0.0305 (17) | −0.0005 (14) | −0.0008 (14) | 0.0055 (13) |
N34 | 0.0414 (15) | 0.0327 (15) | 0.0292 (14) | 0.0042 (12) | 0.0012 (11) | −0.0025 (11) |
C35 | 0.0430 (17) | 0.0312 (18) | 0.0275 (17) | 0.0035 (14) | −0.0059 (13) | −0.0018 (13) |
O35 | 0.0544 (14) | 0.0278 (13) | 0.0471 (14) | 0.0090 (10) | 0.0004 (10) | −0.0033 (10) |
C36 | 0.0363 (16) | 0.0244 (16) | 0.0382 (18) | −0.0006 (12) | −0.0034 (13) | −0.0015 (13) |
C37 | 0.0392 (17) | 0.0355 (18) | 0.0400 (19) | −0.0023 (14) | 0.0002 (14) | 0.0064 (14) |
C38 | 0.0416 (19) | 0.058 (2) | 0.044 (2) | −0.0074 (16) | 0.0063 (15) | 0.0058 (17) |
C39 | 0.0376 (18) | 0.051 (2) | 0.049 (2) | −0.0028 (15) | 0.0070 (15) | −0.0127 (17) |
C310 | 0.0352 (17) | 0.0398 (19) | 0.060 (2) | 0.0023 (14) | −0.0008 (15) | −0.0017 (16) |
C311 | 0.0366 (16) | 0.0347 (18) | 0.0435 (19) | −0.0030 (13) | 0.0052 (14) | 0.0040 (14) |
C312 | 0.0367 (17) | 0.0344 (18) | 0.0393 (19) | −0.0082 (14) | −0.0030 (14) | −0.0044 (14) |
C313 | 0.0361 (17) | 0.0415 (19) | 0.043 (2) | −0.0023 (14) | −0.0015 (14) | −0.0010 (15) |
C314 | 0.052 (2) | 0.048 (2) | 0.044 (2) | −0.0095 (17) | −0.0123 (16) | 0.0079 (17) |
C315 | 0.076 (3) | 0.059 (3) | 0.0304 (19) | −0.024 (2) | −0.0071 (18) | −0.0001 (17) |
C316 | 0.079 (3) | 0.056 (2) | 0.034 (2) | −0.013 (2) | 0.0008 (18) | −0.0128 (18) |
C317 | 0.058 (2) | 0.0396 (19) | 0.037 (2) | −0.0040 (16) | −0.0004 (16) | −0.0100 (15) |
N41 | 0.0393 (14) | 0.0228 (12) | 0.0325 (14) | 0.0031 (10) | −0.0041 (11) | −0.0023 (10) |
C42 | 0.0413 (17) | 0.0297 (17) | 0.0253 (16) | 0.0019 (14) | −0.0004 (12) | 0.0024 (13) |
O42 | 0.0513 (13) | 0.0267 (12) | 0.0388 (13) | 0.0068 (10) | −0.0082 (10) | −0.0011 (9) |
C43 | 0.0396 (16) | 0.0264 (16) | 0.0286 (16) | 0.0027 (13) | −0.0039 (12) | −0.0036 (12) |
N44 | 0.0390 (15) | 0.0227 (14) | 0.0370 (15) | 0.0012 (11) | 0.0003 (11) | −0.0028 (11) |
C45 | 0.0420 (18) | 0.0298 (17) | 0.0282 (17) | 0.0065 (13) | 0.0037 (13) | −0.0015 (12) |
O45 | 0.0526 (13) | 0.0331 (13) | 0.0442 (14) | 0.0135 (11) | 0.0010 (10) | −0.0051 (10) |
C46 | 0.0331 (15) | 0.0357 (18) | 0.0300 (16) | 0.0060 (13) | 0.0012 (12) | −0.0007 (13) |
C47 | 0.0453 (18) | 0.0398 (18) | 0.0344 (18) | 0.0098 (15) | −0.0045 (14) | −0.0018 (14) |
C48 | 0.0411 (18) | 0.060 (2) | 0.0359 (19) | 0.0015 (16) | −0.0052 (14) | −0.0064 (17) |
C49 | 0.0400 (17) | 0.0430 (19) | 0.0358 (18) | −0.0045 (14) | 0.0024 (13) | −0.0082 (14) |
C410 | 0.0433 (18) | 0.0317 (17) | 0.044 (2) | −0.0063 (14) | −0.0043 (14) | −0.0067 (14) |
C411 | 0.0380 (17) | 0.0355 (18) | 0.0434 (19) | 0.0040 (14) | 0.0021 (14) | −0.0067 (15) |
C412 | 0.0352 (16) | 0.0346 (17) | 0.0416 (19) | −0.0045 (13) | 0.0089 (13) | −0.0029 (15) |
C413 | 0.054 (2) | 0.0346 (19) | 0.042 (2) | 0.0011 (15) | 0.0099 (16) | −0.0018 (15) |
C414 | 0.087 (3) | 0.034 (2) | 0.034 (2) | −0.0045 (18) | 0.0135 (18) | −0.0034 (15) |
C415 | 0.090 (3) | 0.047 (2) | 0.032 (2) | −0.002 (2) | 0.0076 (18) | 0.0041 (17) |
C416 | 0.105 (3) | 0.034 (2) | 0.037 (2) | −0.0002 (19) | 0.011 (2) | 0.0049 (15) |
C417 | 0.069 (2) | 0.0292 (18) | 0.039 (2) | −0.0040 (15) | 0.0113 (17) | −0.0004 (14) |
O1W | 0.0531 (15) | 0.0352 (13) | 0.0556 (16) | 0.0082 (11) | 0.0228 (12) | 0.0060 (11) |
O2W | 0.0529 (16) | 0.0472 (15) | 0.0538 (17) | 0.0161 (12) | −0.0180 (12) | −0.0162 (13) |
N11—C12 | 1.321 (4) | N31—C36 | 1.467 (4) |
N11—C16 | 1.466 (4) | C32—O32 | 1.234 (4) |
N11—C110 | 1.468 (4) | C32—C33 | 1.494 (5) |
C12—O12 | 1.248 (4) | C33—N34 | 1.455 (4) |
C12—C13 | 1.515 (4) | C33—C311 | 1.544 (5) |
C13—N14 | 1.453 (4) | C33—H33 | 0.9800 |
C13—C111 | 1.551 (4) | N34—C35 | 1.325 (4) |
C13—H13 | 0.9800 | N34—H34 | 1.04 (3) |
N14—C15 | 1.317 (4) | C35—O35 | 1.240 (4) |
N14—H14 | 0.92 (4) | C35—C36 | 1.507 (5) |
C15—O15 | 1.252 (4) | C36—C37 | 1.538 (4) |
C15—C16 | 1.506 (4) | C36—H36 | 0.9800 |
C16—C17 | 1.520 (4) | C37—C38 | 1.513 (5) |
C16—H16 | 0.9800 | C37—H37A | 0.9700 |
C17—C18 | 1.521 (5) | C37—H37B | 0.9700 |
C17—H17A | 0.9700 | C38—C39 | 1.528 (5) |
C17—H17B | 0.9700 | C38—H38A | 0.9700 |
C18—C19 | 1.520 (5) | C38—H38B | 0.9700 |
C18—H18A | 0.9700 | C39—C310 | 1.523 (5) |
C18—H18B | 0.9700 | C39—H39A | 0.9700 |
C19—C110 | 1.517 (4) | C39—H39B | 0.9700 |
C19—H19A | 0.9700 | C310—H31A | 0.9700 |
C19—H19B | 0.9700 | C310—H31B | 0.9700 |
C110—H11A | 0.9700 | C311—C312 | 1.502 (5) |
C110—H11B | 0.9700 | C311—H31C | 0.9700 |
C111—C112 | 1.505 (5) | C311—H31D | 0.9700 |
C111—H11C | 0.9700 | C312—C317 | 1.393 (5) |
C111—H11D | 0.9700 | C312—C313 | 1.393 (5) |
C112—C113 | 1.381 (5) | C313—C314 | 1.386 (5) |
C112—C117 | 1.391 (5) | C313—H313 | 0.9300 |
C113—C114 | 1.382 (6) | C314—C315 | 1.388 (6) |
C113—H113 | 0.9300 | C314—H314 | 0.9300 |
C114—C115 | 1.382 (6) | C315—C316 | 1.372 (6) |
C114—H114 | 0.9300 | C315—H315 | 0.9300 |
C115—C116 | 1.379 (5) | C316—C317 | 1.386 (5) |
C115—H115 | 0.9300 | C316—H316 | 0.9300 |
C116—C117 | 1.378 (5) | C317—H317 | 0.9300 |
C116—H116 | 0.9300 | N41—C42 | 1.333 (4) |
C117—H117 | 0.9300 | N41—C410 | 1.475 (4) |
N21—C22 | 1.333 (4) | N41—C46 | 1.475 (4) |
N21—C210 | 1.462 (4) | C42—O42 | 1.247 (4) |
N21—C26 | 1.474 (4) | C42—C43 | 1.496 (4) |
C22—O22 | 1.238 (4) | C43—N44 | 1.464 (4) |
C22—C23 | 1.499 (5) | C43—C411 | 1.544 (4) |
C23—N24 | 1.464 (4) | C43—H43 | 0.9800 |
C23—C211 | 1.538 (5) | N44—C45 | 1.318 (4) |
C23—H23 | 0.9800 | N44—H44 | 0.92 (4) |
N24—C25 | 1.328 (4) | C45—O45 | 1.245 (4) |
N24—H24 | 1.01 (3) | C45—C46 | 1.513 (4) |
C25—O25 | 1.254 (4) | C46—C47 | 1.527 (4) |
C25—C26 | 1.493 (4) | C46—H46 | 0.9800 |
C26—C27 | 1.539 (4) | C47—C48 | 1.516 (5) |
C26—H26 | 0.9800 | C47—H47A | 0.9700 |
C27—C28 | 1.522 (5) | C47—H47B | 0.9700 |
C27—H27A | 0.9700 | C48—C49 | 1.514 (5) |
C27—H27B | 0.9700 | C48—H48A | 0.9700 |
C28—C29 | 1.523 (5) | C48—H48B | 0.9700 |
C28—H28A | 0.9700 | C49—C410 | 1.505 (5) |
C28—H28B | 0.9700 | C49—H49A | 0.9700 |
C29—C210 | 1.513 (5) | C49—H49B | 0.9700 |
C29—H29A | 0.9700 | C410—H41A | 0.9700 |
C29—H29B | 0.9700 | C410—H41B | 0.9700 |
C210—H21A | 0.9700 | C411—C412 | 1.499 (5) |
C210—H21B | 0.9700 | C411—H41C | 0.9700 |
C211—C212 | 1.510 (4) | C411—H41D | 0.9700 |
C211—H21C | 0.9700 | C412—C417 | 1.388 (5) |
C211—H21D | 0.9700 | C412—C413 | 1.397 (5) |
C212—C213 | 1.388 (5) | C413—C414 | 1.373 (5) |
C212—C217 | 1.389 (5) | C413—H413 | 0.9300 |
C213—C214 | 1.375 (5) | C414—C415 | 1.380 (5) |
C213—H213 | 0.9300 | C414—H414 | 0.9300 |
C214—C215 | 1.387 (5) | C415—C416 | 1.379 (5) |
C214—H214 | 0.9300 | C415—H415 | 0.9300 |
C215—C216 | 1.376 (5) | C416—C417 | 1.370 (6) |
C215—H215 | 0.9300 | C416—H416 | 0.9300 |
C216—C217 | 1.387 (5) | C417—H417 | 0.9300 |
C216—H216 | 0.9300 | O1W—H11W | 0.95 (5) |
C217—H217 | 0.9300 | O1W—H12W | 0.97 (5) |
N31—C32 | 1.340 (4) | O2W—H21W | 1.02 (5) |
N31—C310 | 1.459 (4) | O2W—H22W | 0.77 (4) |
C12—N11—C16 | 125.1 (2) | C32—N31—C36 | 125.3 (3) |
C12—N11—C110 | 121.4 (3) | C310—N31—C36 | 114.2 (3) |
C16—N11—C110 | 113.4 (2) | O32—C32—N31 | 122.5 (3) |
O12—C12—N11 | 123.4 (3) | O32—C32—C33 | 118.4 (3) |
O12—C12—C13 | 117.1 (3) | N31—C32—C33 | 119.0 (3) |
N11—C12—C13 | 119.4 (3) | N34—C33—C32 | 114.6 (3) |
N14—C13—C12 | 114.0 (2) | N34—C33—C311 | 111.3 (3) |
N14—C13—C111 | 110.7 (2) | C32—C33—C311 | 109.6 (3) |
C12—C13—C111 | 109.7 (2) | N34—C33—H33 | 106.9 |
N14—C13—H13 | 107.4 | C32—C33—H33 | 106.9 |
C12—C13—H13 | 107.4 | C311—C33—H33 | 106.9 |
C111—C13—H13 | 107.4 | C35—N34—C33 | 125.9 (3) |
C15—N14—C13 | 126.1 (3) | C35—N34—H34 | 116.1 (18) |
C15—N14—H14 | 121 (3) | C33—N34—H34 | 117.1 (17) |
C13—N14—H14 | 113 (3) | O35—C35—N34 | 122.2 (3) |
O15—C15—N14 | 122.4 (3) | O35—C35—C36 | 118.7 (3) |
O15—C15—C16 | 118.2 (3) | N34—C35—C36 | 119.1 (3) |
N14—C15—C16 | 119.3 (3) | N31—C36—C35 | 114.3 (3) |
N11—C16—C15 | 114.6 (2) | N31—C36—C37 | 109.8 (3) |
N11—C16—C17 | 109.9 (2) | C35—C36—C37 | 110.5 (2) |
C15—C16—C17 | 111.4 (3) | N31—C36—H36 | 107.3 |
N11—C16—H16 | 106.8 | C35—C36—H36 | 107.3 |
C15—C16—H16 | 106.8 | C37—C36—H36 | 107.3 |
C17—C16—H16 | 106.8 | C38—C37—C36 | 111.8 (3) |
C16—C17—C18 | 111.0 (3) | C38—C37—H37A | 109.2 |
C16—C17—H17A | 109.4 | C36—C37—H37A | 109.2 |
C18—C17—H17A | 109.4 | C38—C37—H37B | 109.2 |
C16—C17—H17B | 109.4 | C36—C37—H37B | 109.2 |
C18—C17—H17B | 109.4 | H37A—C37—H37B | 107.9 |
H17A—C17—H17B | 108.0 | C37—C38—C39 | 111.5 (3) |
C19—C18—C17 | 111.5 (3) | C37—C38—H38A | 109.3 |
C19—C18—H18A | 109.3 | C39—C38—H38A | 109.3 |
C17—C18—H18A | 109.3 | C37—C38—H38B | 109.3 |
C19—C18—H18B | 109.3 | C39—C38—H38B | 109.3 |
C17—C18—H18B | 109.3 | H38A—C38—H38B | 108.0 |
H18A—C18—H18B | 108.0 | C310—C39—C38 | 109.5 (3) |
C110—C19—C18 | 110.5 (3) | C310—C39—H39A | 109.8 |
C110—C19—H19A | 109.5 | C38—C39—H39A | 109.8 |
C18—C19—H19A | 109.5 | C310—C39—H39B | 109.8 |
C110—C19—H19B | 109.5 | C38—C39—H39B | 109.8 |
C18—C19—H19B | 109.5 | H39A—C39—H39B | 108.2 |
H19A—C19—H19B | 108.1 | N31—C310—C39 | 110.1 (3) |
N11—C110—C19 | 110.3 (3) | N31—C310—H31A | 109.6 |
N11—C110—H11A | 109.6 | C39—C310—H31A | 109.6 |
C19—C110—H11A | 109.6 | N31—C310—H31B | 109.6 |
N11—C110—H11B | 109.6 | C39—C310—H31B | 109.6 |
C19—C110—H11B | 109.6 | H31A—C310—H31B | 108.2 |
H11A—C110—H11B | 108.1 | C312—C311—C33 | 113.1 (3) |
C112—C111—C13 | 113.1 (2) | C312—C311—H31C | 109.0 |
C112—C111—H11C | 109.0 | C33—C311—H31C | 109.0 |
C13—C111—H11C | 109.0 | C312—C311—H31D | 109.0 |
C112—C111—H11D | 109.0 | C33—C311—H31D | 109.0 |
C13—C111—H11D | 109.0 | H31C—C311—H31D | 107.8 |
H11C—C111—H11D | 107.8 | C317—C312—C313 | 118.3 (3) |
C113—C112—C117 | 118.3 (3) | C317—C312—C311 | 121.2 (3) |
C113—C112—C111 | 120.9 (3) | C313—C312—C311 | 120.5 (3) |
C117—C112—C111 | 120.8 (3) | C314—C313—C312 | 120.8 (3) |
C112—C113—C114 | 120.7 (3) | C314—C313—H313 | 119.6 |
C112—C113—H113 | 119.7 | C312—C313—H313 | 119.6 |
C114—C113—H113 | 119.7 | C313—C314—C315 | 119.6 (4) |
C115—C114—C113 | 120.6 (4) | C313—C314—H314 | 120.2 |
C115—C114—H114 | 119.7 | C315—C314—H314 | 120.2 |
C113—C114—H114 | 119.7 | C316—C315—C314 | 120.4 (4) |
C116—C115—C114 | 119.0 (4) | C316—C315—H315 | 119.8 |
C116—C115—H115 | 120.5 | C314—C315—H315 | 119.8 |
C114—C115—H115 | 120.5 | C315—C316—C317 | 119.9 (4) |
C117—C116—C115 | 120.4 (3) | C315—C316—H316 | 120.1 |
C117—C116—H116 | 119.8 | C317—C316—H316 | 120.1 |
C115—C116—H116 | 119.8 | C316—C317—C312 | 120.9 (3) |
C116—C117—C112 | 120.9 (3) | C316—C317—H317 | 119.5 |
C116—C117—H117 | 119.5 | C312—C317—H317 | 119.5 |
C112—C117—H117 | 119.5 | C42—N41—C410 | 120.9 (2) |
C22—N21—C210 | 120.5 (2) | C42—N41—C46 | 125.0 (2) |
C22—N21—C26 | 125.4 (2) | C410—N41—C46 | 114.0 (2) |
C210—N21—C26 | 113.5 (2) | O42—C42—N41 | 122.3 (3) |
O22—C22—N21 | 122.7 (3) | O42—C42—C43 | 118.0 (3) |
O22—C22—C23 | 117.7 (3) | N41—C42—C43 | 119.7 (3) |
N21—C22—C23 | 119.5 (3) | N44—C43—C42 | 114.3 (2) |
N24—C23—C22 | 113.7 (3) | N44—C43—C411 | 110.4 (2) |
N24—C23—C211 | 110.9 (3) | C42—C43—C411 | 109.0 (2) |
C22—C23—C211 | 110.5 (3) | N44—C43—H43 | 107.6 |
N24—C23—H23 | 107.1 | C42—C43—H43 | 107.6 |
C22—C23—H23 | 107.1 | C411—C43—H43 | 107.6 |
C211—C23—H23 | 107.1 | C45—N44—C43 | 126.1 (3) |
C25—N24—C23 | 125.5 (3) | C45—N44—H44 | 120 (2) |
C25—N24—H24 | 121.0 (17) | C43—N44—H44 | 111 (2) |
C23—N24—H24 | 111.4 (17) | O45—C45—N44 | 122.8 (3) |
O25—C25—N24 | 121.3 (3) | O45—C45—C46 | 117.9 (3) |
O25—C25—C26 | 118.7 (3) | N44—C45—C46 | 119.3 (3) |
N24—C25—C26 | 120.0 (3) | N41—C46—C45 | 114.5 (2) |
N21—C26—C25 | 113.7 (2) | N41—C46—C47 | 110.3 (2) |
N21—C26—C27 | 109.7 (2) | C45—C46—C47 | 111.0 (3) |
C25—C26—C27 | 110.8 (2) | N41—C46—H46 | 106.9 |
N21—C26—H26 | 107.5 | C45—C46—H46 | 106.9 |
C25—C26—H26 | 107.5 | C47—C46—H46 | 106.9 |
C27—C26—H26 | 107.5 | C48—C47—C46 | 111.4 (3) |
C28—C27—C26 | 111.7 (3) | C48—C47—H47A | 109.3 |
C28—C27—H27A | 109.3 | C46—C47—H47A | 109.3 |
C26—C27—H27A | 109.3 | C48—C47—H47B | 109.3 |
C28—C27—H27B | 109.3 | C46—C47—H47B | 109.3 |
C26—C27—H27B | 109.3 | H47A—C47—H47B | 108.0 |
H27A—C27—H27B | 107.9 | C49—C48—C47 | 110.9 (3) |
C27—C28—C29 | 111.7 (3) | C49—C48—H48A | 109.5 |
C27—C28—H28A | 109.3 | C47—C48—H48A | 109.5 |
C29—C28—H28A | 109.3 | C49—C48—H48B | 109.5 |
C27—C28—H28B | 109.3 | C47—C48—H48B | 109.5 |
C29—C28—H28B | 109.3 | H48A—C48—H48B | 108.0 |
H28A—C28—H28B | 107.9 | C410—C49—C48 | 110.8 (3) |
C210—C29—C28 | 109.8 (3) | C410—C49—H49A | 109.5 |
C210—C29—H29A | 109.7 | C48—C49—H49A | 109.5 |
C28—C29—H29A | 109.7 | C410—C49—H49B | 109.5 |
C210—C29—H29B | 109.7 | C48—C49—H49B | 109.5 |
C28—C29—H29B | 109.7 | H49A—C49—H49B | 108.1 |
H29A—C29—H29B | 108.2 | N41—C410—C49 | 110.4 (3) |
N21—C210—C29 | 109.7 (3) | N41—C410—H41A | 109.6 |
N21—C210—H21A | 109.7 | C49—C410—H41A | 109.6 |
C29—C210—H21A | 109.7 | N41—C410—H41B | 109.6 |
N21—C210—H21B | 109.7 | C49—C410—H41B | 109.6 |
C29—C210—H21B | 109.7 | H41A—C410—H41B | 108.1 |
H21A—C210—H21B | 108.2 | C412—C411—C43 | 113.3 (3) |
C212—C211—C23 | 112.9 (2) | C412—C411—H41C | 108.9 |
C212—C211—H21C | 109.0 | C43—C411—H41C | 108.9 |
C23—C211—H21C | 109.0 | C412—C411—H41D | 108.9 |
C212—C211—H21D | 109.0 | C43—C411—H41D | 108.9 |
C23—C211—H21D | 109.0 | H41C—C411—H41D | 107.7 |
H21C—C211—H21D | 107.8 | C417—C412—C413 | 117.2 (3) |
C213—C212—C217 | 118.2 (3) | C417—C412—C411 | 121.7 (3) |
C213—C212—C211 | 120.9 (3) | C413—C412—C411 | 121.0 (3) |
C217—C212—C211 | 120.8 (3) | C414—C413—C412 | 121.5 (3) |
C214—C213—C212 | 121.4 (3) | C414—C413—H413 | 119.3 |
C214—C213—H213 | 119.3 | C412—C413—H413 | 119.3 |
C212—C213—H213 | 119.3 | C413—C414—C415 | 120.0 (3) |
C213—C214—C215 | 119.6 (3) | C413—C414—H414 | 120.0 |
C213—C214—H214 | 120.2 | C415—C414—H414 | 120.0 |
C215—C214—H214 | 120.2 | C416—C415—C414 | 119.3 (4) |
C216—C215—C214 | 119.9 (3) | C416—C415—H415 | 120.3 |
C216—C215—H215 | 120.0 | C414—C415—H415 | 120.3 |
C214—C215—H215 | 120.0 | C417—C416—C415 | 120.5 (3) |
C215—C216—C217 | 120.1 (3) | C417—C416—H416 | 119.8 |
C215—C216—H216 | 120.0 | C415—C416—H416 | 119.8 |
C217—C216—H216 | 120.0 | C416—C417—C412 | 121.4 (3) |
C216—C217—C212 | 120.7 (3) | C416—C417—H417 | 119.3 |
C216—C217—H217 | 119.6 | C412—C417—H417 | 119.3 |
C212—C217—H217 | 119.6 | H11W—O1W—H12W | 107 (4) |
C32—N31—C310 | 120.3 (3) | H21W—O2W—H22W | 89 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14···O25i | 0.92 (4) | 2.00 (4) | 2.848 (3) | 154 (4) |
N24—H24···O2W | 1.01 (3) | 1.82 (3) | 2.826 (4) | 176 (3) |
N34—H34···O1W | 1.04 (3) | 1.84 (4) | 2.864 (4) | 166 (3) |
N44—H44···O35ii | 0.92 (4) | 1.94 (4) | 2.836 (3) | 162 (3) |
O1W—H11W···O12iii | 0.95 (5) | 1.95 (5) | 2.893 (3) | 169 (4) |
O1W—H12W···O45iv | 0.97 (5) | 1.82 (5) | 2.792 (3) | 173 (4) |
O2W—H21W···O42v | 1.02 (5) | 1.85 (5) | 2.826 (3) | 161 (4) |
O2W—H22W···O15vi | 0.77 (4) | 1.99 (4) | 2.760 (4) | 176 (4) |
Symmetry codes: (i) −x+2, y+1/2, −z+1; (ii) −x+1, y−1/2, −z; (iii) x−1, y, z; (iv) −x+1, y+1/2, −z; (v) x+1, y, z+1; (vi) −x+2, y−1/2, −z+1. |
2(C15H18N2O2)·H2O | F(000) = 1144 |
Mr = 534.64 | Dx = 1.236 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3230 reflections |
a = 8.5217 (1) Å | θ = 1–26.0° |
b = 25.0552 (3) Å | µ = 0.09 mm−1 |
c = 13.4521 (2) Å | T = 297 K |
V = 2872.20 (6) Å3 | Prism, colourless |
Z = 4 | 0.4 × 0.4 × 0.3 mm |
Nonius KappaCCD area detector diffractometer | 4670 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.032 |
Graphite monochromator | θmax = 26.0°, θmin = 2.9° |
Detector resolution: 9.091 pixels mm-1 | h = −10→10 |
φ and ω scans to fill the Ewald sphere | k = −30→30 |
50418 measured reflections | l = −16→16 |
5656 independent reflections |
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)] = 0.035 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0538P)2 + 0.1118P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
5656 reflections | Δρmax = 0.09 e Å−3 |
368 parameters | Δρmin = −0.12 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.0 (8) |
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 | ||
N11 | 0.63236 (14) | 0.83973 (4) | 0.84175 (9) | 0.0579 (3) | |
C12 | 0.77696 (18) | 0.84296 (5) | 0.87773 (10) | 0.0553 (3) | |
O12 | 0.84440 (14) | 0.88591 (4) | 0.89221 (9) | 0.0720 (3) | |
C13 | 0.86689 (18) | 0.79218 (5) | 0.89793 (11) | 0.0589 (3) | |
H13 | 0.9119 | 0.7953 | 0.9647 | 0.071* | |
N14 | 0.77031 (16) | 0.74429 (5) | 0.89675 (10) | 0.0610 (3) | |
C15 | 0.62316 (19) | 0.74101 (6) | 0.86763 (11) | 0.0604 (4) | |
O15 | 0.54895 (16) | 0.69850 (5) | 0.86889 (10) | 0.0844 (4) | |
C16 | 0.54071 (18) | 0.79064 (6) | 0.83340 (11) | 0.0609 (4) | |
H16 | 0.4478 | 0.7950 | 0.8756 | 0.073* | |
C17 | 0.4824 (2) | 0.78427 (7) | 0.72644 (14) | 0.0818 (5) | |
H17A | 0.5712 | 0.7779 | 0.6829 | 0.098* | |
H17B | 0.4134 | 0.7536 | 0.7225 | 0.098* | |
C18 | 0.3947 (2) | 0.83366 (8) | 0.69159 (16) | 0.0919 (6) | |
H18A | 0.3682 | 0.8298 | 0.6218 | 0.110* | |
H18B | 0.2978 | 0.8371 | 0.7288 | 0.110* | |
C19 | 0.4926 (2) | 0.88315 (7) | 0.70573 (14) | 0.0737 (4) | |
H19A | 0.5831 | 0.8817 | 0.6621 | 0.088* | |
H19B | 0.4312 | 0.9143 | 0.6880 | 0.088* | |
C110 | 0.5467 (2) | 0.88809 (6) | 0.81155 (14) | 0.0752 (5) | |
H11A | 0.6146 | 0.9190 | 0.8181 | 0.090* | |
H11B | 0.4568 | 0.8932 | 0.8547 | 0.090* | |
C111 | 1.00439 (19) | 0.78751 (7) | 0.82460 (15) | 0.0767 (5) | |
H11C | 1.0741 | 0.8177 | 0.8341 | 0.092* | |
H11D | 1.0631 | 0.7553 | 0.8396 | 0.092* | |
C112 | 0.9539 (2) | 0.78585 (6) | 0.71764 (14) | 0.0735 (5) | |
C113 | 0.9171 (3) | 0.73810 (7) | 0.67201 (16) | 0.1061 (8) | |
H113 | 0.9285 | 0.7064 | 0.7071 | 0.127* | |
C114 | 0.8636 (5) | 0.73664 (8) | 0.57504 (18) | 0.1467 (14) | |
H114 | 0.8364 | 0.7042 | 0.5460 | 0.176* | |
C115 | 0.8506 (5) | 0.78322 (10) | 0.52162 (17) | 0.1411 (12) | |
H115 | 0.8185 | 0.7824 | 0.4556 | 0.169* | |
C116 | 0.8854 (4) | 0.83097 (8) | 0.56638 (16) | 0.1141 (9) | |
H116 | 0.8738 | 0.8626 | 0.5310 | 0.137* | |
C117 | 0.9373 (3) | 0.83237 (7) | 0.66291 (14) | 0.0858 (5) | |
H117 | 0.9616 | 0.8650 | 0.6920 | 0.103* | |
N21 | 0.77816 (15) | 1.04333 (5) | 0.62535 (10) | 0.0614 (3) | |
C22 | 0.8780 (2) | 1.00617 (6) | 0.59378 (12) | 0.0633 (4) | |
O22 | 0.84629 (16) | 0.95843 (4) | 0.59176 (12) | 0.0929 (4) | |
C23 | 1.0399 (2) | 1.02300 (6) | 0.56222 (12) | 0.0638 (4) | |
H23 | 1.0594 | 1.0071 | 0.4968 | 0.077* | |
N24 | 1.05910 (18) | 1.08021 (5) | 0.55155 (10) | 0.0653 (3) | |
C25 | 0.9599 (2) | 1.11740 (6) | 0.58351 (11) | 0.0602 (4) | |
O25 | 0.98891 (15) | 1.16573 (4) | 0.57477 (10) | 0.0789 (3) | |
C26 | 0.80946 (17) | 1.10054 (5) | 0.63188 (11) | 0.0567 (3) | |
H26 | 0.7243 | 1.1187 | 0.5966 | 0.068* | |
C27 | 0.8033 (2) | 1.11915 (7) | 0.73919 (13) | 0.0688 (4) | |
H27A | 0.8106 | 1.1578 | 0.7413 | 0.083* | |
H27B | 0.8922 | 1.1046 | 0.7752 | 0.083* | |
C28 | 0.6516 (2) | 1.10147 (8) | 0.78946 (15) | 0.0844 (5) | |
H28A | 0.6564 | 1.1101 | 0.8597 | 0.101* | |
H28B | 0.5640 | 1.1208 | 0.7608 | 0.101* | |
C29 | 0.6249 (2) | 1.04195 (7) | 0.77724 (15) | 0.0824 (5) | |
H29A | 0.7061 | 1.0224 | 0.8122 | 0.099* | |
H29B | 0.5243 | 1.0322 | 0.8058 | 0.099* | |
C210 | 0.6276 (2) | 1.02739 (7) | 0.66901 (15) | 0.0780 (5) | |
H21A | 0.6133 | 0.9892 | 0.6616 | 0.094* | |
H21B | 0.5425 | 1.0453 | 0.6347 | 0.094* | |
C211 | 1.16240 (19) | 0.99973 (6) | 0.63384 (13) | 0.0697 (4) | |
H21C | 1.1520 | 0.9612 | 0.6347 | 0.084* | |
H21D | 1.2664 | 1.0081 | 0.6091 | 0.084* | |
C212 | 1.14780 (18) | 1.02024 (6) | 0.73819 (12) | 0.0642 (4) | |
C213 | 1.0564 (2) | 0.99376 (7) | 0.80807 (14) | 0.0795 (5) | |
H213 | 1.0075 | 0.9619 | 0.7907 | 0.095* | |
C214 | 1.0373 (3) | 1.01363 (10) | 0.90161 (16) | 0.1046 (7) | |
H214 | 0.9751 | 0.9955 | 0.9473 | 0.126* | |
C215 | 1.1103 (4) | 1.06074 (11) | 0.92851 (16) | 0.1113 (8) | |
H215 | 1.0969 | 1.0745 | 0.9922 | 0.134* | |
C216 | 1.2039 (3) | 1.08747 (10) | 0.85996 (18) | 0.0975 (6) | |
H216 | 1.2553 | 1.1187 | 0.8782 | 0.117* | |
C217 | 1.2200 (2) | 1.06777 (7) | 0.76604 (14) | 0.0766 (5) | |
H217 | 1.2802 | 1.0864 | 0.7199 | 0.092* | |
O1W | 1.37246 (19) | 1.11314 (6) | 0.50808 (13) | 0.0964 (5) | |
H1W | 1.457 (3) | 1.1103 (8) | 0.4690 (19) | 0.106 (7)* | |
H2W | 1.396 (3) | 1.1395 (8) | 0.5503 (17) | 0.094 (7)* | |
H14 | 0.824 (2) | 0.7136 (8) | 0.9122 (14) | 0.078 (5)* | |
H24 | 1.152 (3) | 1.0946 (8) | 0.5249 (16) | 0.096 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0667 (7) | 0.0527 (6) | 0.0542 (7) | −0.0026 (6) | −0.0086 (6) | 0.0017 (5) |
C12 | 0.0704 (8) | 0.0504 (7) | 0.0451 (7) | −0.0057 (7) | −0.0064 (7) | 0.0001 (6) |
O12 | 0.0902 (8) | 0.0507 (5) | 0.0751 (7) | −0.0113 (5) | −0.0250 (6) | 0.0012 (5) |
C13 | 0.0671 (8) | 0.0527 (7) | 0.0568 (8) | −0.0077 (7) | −0.0107 (7) | 0.0062 (6) |
N14 | 0.0726 (8) | 0.0483 (6) | 0.0621 (8) | −0.0050 (6) | −0.0024 (6) | 0.0062 (6) |
C15 | 0.0744 (9) | 0.0580 (8) | 0.0487 (8) | −0.0151 (7) | 0.0021 (7) | 0.0033 (6) |
O15 | 0.0993 (8) | 0.0676 (7) | 0.0863 (9) | −0.0333 (6) | −0.0051 (7) | 0.0125 (6) |
C16 | 0.0603 (8) | 0.0678 (8) | 0.0546 (8) | −0.0140 (7) | 0.0000 (7) | 0.0063 (7) |
C17 | 0.0985 (12) | 0.0798 (10) | 0.0672 (11) | −0.0273 (10) | −0.0253 (10) | 0.0030 (9) |
C18 | 0.0882 (12) | 0.1103 (15) | 0.0772 (12) | −0.0160 (11) | −0.0295 (10) | 0.0142 (11) |
C19 | 0.0723 (10) | 0.0803 (10) | 0.0686 (10) | 0.0025 (8) | −0.0104 (8) | 0.0149 (8) |
C110 | 0.0845 (11) | 0.0647 (9) | 0.0764 (11) | 0.0116 (8) | −0.0162 (9) | 0.0016 (8) |
C111 | 0.0656 (9) | 0.0655 (9) | 0.0991 (14) | −0.0016 (8) | 0.0049 (9) | 0.0155 (9) |
C112 | 0.0842 (10) | 0.0580 (8) | 0.0782 (11) | 0.0065 (8) | 0.0266 (9) | 0.0057 (8) |
C113 | 0.180 (2) | 0.0575 (10) | 0.0805 (14) | 0.0161 (12) | 0.0307 (15) | 0.0031 (9) |
C114 | 0.298 (4) | 0.0696 (12) | 0.0722 (14) | 0.0027 (18) | 0.027 (2) | −0.0147 (10) |
C115 | 0.268 (4) | 0.0950 (15) | 0.0607 (12) | 0.013 (2) | 0.0222 (18) | −0.0067 (11) |
C116 | 0.202 (3) | 0.0740 (12) | 0.0658 (12) | 0.0190 (15) | 0.0353 (15) | 0.0061 (9) |
C117 | 0.1235 (15) | 0.0598 (9) | 0.0742 (12) | 0.0031 (9) | 0.0265 (11) | 0.0060 (8) |
N21 | 0.0626 (7) | 0.0530 (6) | 0.0685 (8) | −0.0087 (5) | −0.0032 (6) | 0.0028 (6) |
C22 | 0.0743 (9) | 0.0512 (8) | 0.0643 (9) | −0.0053 (7) | −0.0064 (8) | −0.0035 (7) |
O22 | 0.0978 (9) | 0.0527 (6) | 0.1282 (11) | −0.0118 (6) | −0.0003 (9) | −0.0102 (7) |
C23 | 0.0796 (10) | 0.0576 (8) | 0.0544 (8) | −0.0013 (8) | 0.0065 (8) | −0.0065 (7) |
N24 | 0.0738 (8) | 0.0646 (7) | 0.0574 (8) | −0.0072 (7) | 0.0083 (7) | 0.0049 (6) |
C25 | 0.0747 (9) | 0.0557 (8) | 0.0503 (8) | −0.0092 (7) | −0.0063 (7) | 0.0050 (6) |
O25 | 0.0970 (8) | 0.0546 (6) | 0.0851 (8) | −0.0149 (6) | 0.0012 (7) | 0.0095 (5) |
C26 | 0.0620 (8) | 0.0474 (7) | 0.0608 (9) | −0.0020 (6) | −0.0101 (7) | 0.0052 (6) |
C27 | 0.0706 (9) | 0.0707 (9) | 0.0650 (10) | −0.0005 (8) | 0.0003 (8) | −0.0074 (7) |
C28 | 0.0716 (11) | 0.1056 (14) | 0.0760 (12) | 0.0059 (10) | 0.0121 (9) | −0.0068 (10) |
C29 | 0.0624 (9) | 0.0927 (12) | 0.0921 (14) | 0.0037 (9) | 0.0112 (10) | 0.0239 (10) |
C210 | 0.0611 (9) | 0.0682 (10) | 0.1045 (15) | −0.0126 (8) | −0.0011 (10) | 0.0090 (9) |
C211 | 0.0662 (9) | 0.0649 (9) | 0.0781 (11) | 0.0076 (7) | 0.0108 (8) | −0.0057 (8) |
C212 | 0.0588 (8) | 0.0639 (8) | 0.0699 (10) | 0.0127 (7) | −0.0063 (8) | 0.0041 (7) |
C213 | 0.0947 (12) | 0.0742 (10) | 0.0696 (11) | 0.0077 (9) | −0.0050 (10) | 0.0195 (8) |
C214 | 0.1396 (19) | 0.1120 (16) | 0.0621 (12) | 0.0286 (15) | 0.0025 (13) | 0.0226 (12) |
C215 | 0.150 (2) | 0.1270 (19) | 0.0565 (12) | 0.0504 (17) | −0.0271 (14) | −0.0073 (12) |
C216 | 0.1014 (14) | 0.1002 (14) | 0.0909 (16) | 0.0190 (12) | −0.0348 (13) | −0.0210 (12) |
C217 | 0.0617 (9) | 0.0824 (11) | 0.0857 (13) | 0.0038 (8) | −0.0091 (9) | −0.0022 (9) |
O1W | 0.0936 (9) | 0.0821 (8) | 0.1135 (12) | −0.0221 (7) | 0.0506 (9) | −0.0231 (8) |
N11—C12 | 1.3264 (19) | N21—C26 | 1.4606 (17) |
N11—C16 | 1.4612 (18) | N21—C210 | 1.466 (2) |
N11—C110 | 1.4715 (19) | C22—O22 | 1.2267 (16) |
C12—O12 | 1.2355 (16) | C22—C23 | 1.504 (2) |
C12—C13 | 1.510 (2) | C23—N24 | 1.450 (2) |
C13—N14 | 1.4552 (18) | C23—C211 | 1.535 (2) |
C13—C111 | 1.536 (2) | C23—H23 | 0.9800 |
C13—H13 | 0.9800 | N24—C25 | 1.329 (2) |
N14—C15 | 1.316 (2) | N24—H24 | 0.94 (2) |
N14—H14 | 0.918 (19) | C25—O25 | 1.2415 (17) |
C15—O15 | 1.2388 (17) | C25—C26 | 1.499 (2) |
C15—C16 | 1.501 (2) | C26—C27 | 1.518 (2) |
C16—C17 | 1.531 (2) | C26—H26 | 0.9800 |
C16—H16 | 0.9800 | C27—C28 | 1.524 (3) |
C17—C18 | 1.519 (3) | C27—H27A | 0.9700 |
C17—H17A | 0.9700 | C27—H27B | 0.9700 |
C17—H17B | 0.9700 | C28—C29 | 1.518 (3) |
C18—C19 | 1.507 (2) | C28—H28A | 0.9700 |
C18—H18A | 0.9700 | C28—H28B | 0.9700 |
C18—H18B | 0.9700 | C29—C210 | 1.501 (3) |
C19—C110 | 1.501 (3) | C29—H29A | 0.9700 |
C19—H19A | 0.9700 | C29—H29B | 0.9700 |
C19—H19B | 0.9700 | C210—H21A | 0.9700 |
C110—H11A | 0.9700 | C210—H21B | 0.9700 |
C110—H11B | 0.9700 | C211—C212 | 1.500 (2) |
C111—C112 | 1.502 (3) | C211—H21C | 0.9700 |
C111—H11C | 0.9700 | C211—H21D | 0.9700 |
C111—H11D | 0.9700 | C212—C213 | 1.389 (3) |
C112—C113 | 1.381 (3) | C212—C217 | 1.392 (2) |
C112—C117 | 1.386 (2) | C213—C214 | 1.363 (3) |
C113—C114 | 1.382 (4) | C213—H213 | 0.9300 |
C113—H113 | 0.9300 | C214—C215 | 1.382 (3) |
C114—C115 | 1.375 (3) | C214—H214 | 0.9300 |
C114—H114 | 0.9300 | C215—C216 | 1.391 (4) |
C115—C116 | 1.372 (3) | C215—H215 | 0.9300 |
C115—H115 | 0.9300 | C216—C217 | 1.363 (3) |
C116—C117 | 1.372 (3) | C216—H216 | 0.9300 |
C116—H116 | 0.9300 | C217—H217 | 0.9300 |
C117—H117 | 0.9300 | O1W—H1W | 0.89 (3) |
N21—C22 | 1.331 (2) | O1W—H2W | 0.89 (2) |
C12—N11—C16 | 125.16 (12) | C22—N21—C210 | 119.78 (13) |
C12—N11—C110 | 120.74 (12) | C26—N21—C210 | 113.76 (13) |
C16—N11—C110 | 114.01 (12) | O22—C22—N21 | 123.24 (16) |
O12—C12—N11 | 122.87 (13) | O22—C22—C23 | 117.99 (15) |
O12—C12—C13 | 118.00 (13) | N21—C22—C23 | 118.73 (12) |
N11—C12—C13 | 119.07 (12) | N24—C23—C22 | 114.10 (14) |
N14—C13—C12 | 113.94 (13) | N24—C23—C211 | 111.16 (13) |
N14—C13—C111 | 111.19 (13) | C22—C23—C211 | 109.88 (13) |
C12—C13—C111 | 109.62 (12) | N24—C23—H23 | 107.1 |
N14—C13—H13 | 107.3 | C22—C23—H23 | 107.1 |
C12—C13—H13 | 107.3 | C211—C23—H23 | 107.1 |
C111—C13—H13 | 107.3 | C25—N24—C23 | 126.11 (14) |
C15—N14—C13 | 126.41 (13) | C25—N24—H24 | 112.9 (12) |
C15—N14—H14 | 119.2 (11) | C23—N24—H24 | 120.7 (12) |
C13—N14—H14 | 114.1 (11) | O25—C25—N24 | 121.77 (15) |
O15—C15—N14 | 122.41 (15) | O25—C25—C26 | 119.10 (15) |
O15—C15—C16 | 118.53 (14) | N24—C25—C26 | 119.13 (13) |
N14—C15—C16 | 119.05 (12) | N21—C26—C25 | 114.00 (12) |
N11—C16—C15 | 115.07 (12) | N21—C26—C27 | 110.63 (12) |
N11—C16—C17 | 109.49 (12) | C25—C26—C27 | 110.86 (12) |
C15—C16—C17 | 110.74 (14) | N21—C26—H26 | 107.0 |
N11—C16—H16 | 107.1 | C25—C26—H26 | 107.0 |
C15—C16—H16 | 107.1 | C27—C26—H26 | 107.0 |
C17—C16—H16 | 107.1 | C26—C27—C28 | 111.22 (14) |
C18—C17—C16 | 111.39 (16) | C26—C27—H27A | 109.4 |
C18—C17—H17A | 109.3 | C28—C27—H27A | 109.4 |
C16—C17—H17A | 109.3 | C26—C27—H27B | 109.4 |
C18—C17—H17B | 109.3 | C28—C27—H27B | 109.4 |
C16—C17—H17B | 109.3 | H27A—C27—H27B | 108.0 |
H17A—C17—H17B | 108.0 | C29—C28—C27 | 111.41 (15) |
C19—C18—C17 | 111.05 (15) | C29—C28—H28A | 109.3 |
C19—C18—H18A | 109.4 | C27—C28—H28A | 109.3 |
C17—C18—H18A | 109.4 | C29—C28—H28B | 109.3 |
C19—C18—H18B | 109.4 | C27—C28—H28B | 109.3 |
C17—C18—H18B | 109.4 | H28A—C28—H28B | 108.0 |
H18A—C18—H18B | 108.0 | C210—C29—C28 | 109.97 (15) |
C110—C19—C18 | 110.95 (15) | C210—C29—H29A | 109.7 |
C110—C19—H19A | 109.4 | C28—C29—H29A | 109.7 |
C18—C19—H19A | 109.4 | C210—C29—H29B | 109.7 |
C110—C19—H19B | 109.4 | C28—C29—H29B | 109.7 |
C18—C19—H19B | 109.4 | H29A—C29—H29B | 108.2 |
H19A—C19—H19B | 108.0 | N21—C210—C29 | 109.64 (15) |
N11—C110—C19 | 110.26 (14) | N21—C210—H21A | 109.7 |
N11—C110—H11A | 109.6 | C29—C210—H21A | 109.7 |
C19—C110—H11A | 109.6 | N21—C210—H21B | 109.7 |
N11—C110—H11B | 109.6 | C29—C210—H21B | 109.7 |
C19—C110—H11B | 109.6 | H21A—C210—H21B | 108.2 |
H11A—C110—H11B | 108.1 | C212—C211—C23 | 113.63 (13) |
C112—C111—C13 | 113.50 (14) | C212—C211—H21C | 108.8 |
C112—C111—H11C | 108.9 | C23—C211—H21C | 108.8 |
C13—C111—H11C | 108.9 | C212—C211—H21D | 108.8 |
C112—C111—H11D | 108.9 | C23—C211—H21D | 108.8 |
C13—C111—H11D | 108.9 | H21C—C211—H21D | 107.7 |
H11C—C111—H11D | 107.7 | C213—C212—C217 | 118.31 (17) |
C113—C112—C117 | 117.99 (19) | C213—C212—C211 | 121.07 (16) |
C113—C112—C111 | 120.99 (16) | C217—C212—C211 | 120.55 (16) |
C117—C112—C111 | 120.98 (17) | C214—C213—C212 | 121.2 (2) |
C112—C113—C114 | 121.16 (18) | C214—C213—H213 | 119.4 |
C112—C113—H113 | 119.4 | C212—C213—H213 | 119.4 |
C114—C113—H113 | 119.4 | C213—C214—C215 | 120.0 (2) |
C115—C114—C113 | 119.8 (2) | C213—C214—H214 | 120.0 |
C115—C114—H114 | 120.1 | C215—C214—H214 | 120.0 |
C113—C114—H114 | 120.1 | C214—C215—C216 | 119.7 (2) |
C116—C115—C114 | 119.6 (2) | C214—C215—H215 | 120.1 |
C116—C115—H115 | 120.2 | C216—C215—H215 | 120.1 |
C114—C115—H115 | 120.2 | C217—C216—C215 | 119.9 (2) |
C115—C116—C117 | 120.5 (2) | C217—C216—H216 | 120.1 |
C115—C116—H116 | 119.8 | C215—C216—H216 | 120.1 |
C117—C116—H116 | 119.8 | C216—C217—C212 | 121.0 (2) |
C116—C117—C112 | 120.94 (18) | C216—C217—H217 | 119.5 |
C116—C117—H117 | 119.5 | C212—C217—H217 | 119.5 |
C112—C117—H117 | 119.5 | H1W—O1W—H2W | 105 (2) |
C22—N21—C26 | 126.08 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W···O12i | 0.89 (3) | 1.99 (3) | 2.8726 (18) | 171 (2) |
O1W—H2W···O15ii | 0.89 (2) | 1.89 (2) | 2.786 (2) | 176 (2) |
N14—H14···O25iii | 0.918 (19) | 2.004 (19) | 2.8690 (18) | 156.5 (15) |
N24—H24···O1W | 0.94 (2) | 1.95 (2) | 2.855 (2) | 161.3 (19) |
Symmetry codes: (i) −x+5/2, −y+2, z−1/2; (ii) −x+2, y+1/2, −z+3/2; (iii) −x+2, y−1/2, −z+3/2. |
C15H18N2O2 | F(000) = 1656 |
Mr = 258.31 | Dx = 1.235 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71070 Å |
Hall symbol: P 2yb | Cell parameters from 62657 reflections |
a = 22.1154 (7) Å | θ = 1–25° |
b = 6.3963 (2) Å | µ = 0.08 mm−1 |
c = 29.5771 (7) Å | T = 150 K |
β = 95.2660 (18)° | Prism, colourless |
V = 4166.2 (2) Å3 | 0.35 × 0.35 × 0.2 mm |
Z = 12 |
Nonius KappaCCD area detector diffractometer | 9326 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
Graphite monochromator | θmax = 25.1°, θmin = 1.2° |
Detector resolution: 9.091 pixels mm-1 | h = −26→26 |
φ and ω scans to fill the Ewald sphere | k = −7→7 |
64641 measured reflections | l = −34→35 |
14267 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.066 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.144 | w = 1/[σ2(Fo2) + (0.0145P)2 + 2.6049P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max = 0.004 |
14267 reflections | Δρmax = 0.19 e Å−3 |
1051 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.1 (11) |
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 | ||
N11 | −0.18810 (13) | 0.4965 (5) | 0.85758 (8) | 0.0257 (7) | |
C12 | −0.18332 (15) | 0.3068 (6) | 0.87631 (11) | 0.0266 (8) | |
C13 | −0.20288 (15) | 0.2767 (6) | 0.92324 (11) | 0.0294 (8) | |
H13 | −0.2279 | 0.1501 | 0.9224 | 0.035* | |
N14 | −0.23990 (13) | 0.4468 (5) | 0.93812 (9) | 0.0261 (7) | |
C15 | −0.24115 (15) | 0.6423 (6) | 0.92199 (10) | 0.0224 (8) | |
C16 | −0.21632 (15) | 0.6804 (5) | 0.87695 (10) | 0.0226 (8) | |
H16 | −0.1851 | 0.7891 | 0.8815 | 0.027* | |
C17 | −0.26619 (16) | 0.7631 (6) | 0.84289 (10) | 0.0316 (9) | |
H17A | −0.2813 | 0.8938 | 0.8541 | 0.038* | |
H17B | −0.2996 | 0.6641 | 0.8403 | 0.038* | |
C18 | −0.24460 (18) | 0.7995 (7) | 0.79582 (10) | 0.0389 (10) | |
H18A | −0.2791 | 0.8352 | 0.7745 | 0.047* | |
H18B | −0.2164 | 0.9159 | 0.7971 | 0.047* | |
C19 | −0.21369 (17) | 0.6048 (6) | 0.77938 (10) | 0.0334 (9) | |
H19A | −0.2432 | 0.4931 | 0.7744 | 0.040* | |
H19B | −0.1972 | 0.6343 | 0.7508 | 0.040* | |
C110 | −0.16345 (16) | 0.5370 (6) | 0.81404 (10) | 0.0342 (9) | |
H11A | −0.1445 | 0.4112 | 0.8037 | 0.041* | |
H11B | −0.1328 | 0.6455 | 0.8178 | 0.041* | |
C111 | −0.14745 (17) | 0.2368 (6) | 0.95717 (12) | 0.0358 (10) | |
H11C | −0.1609 | 0.1986 | 0.9863 | 0.043* | |
H11D | −0.1242 | 0.1209 | 0.9466 | 0.043* | |
C112 | −0.10734 (17) | 0.4284 (6) | 0.96277 (11) | 0.0316 (9) | |
C113 | −0.11505 (18) | 0.5732 (6) | 0.99712 (11) | 0.0362 (10) | |
H113 | −0.1440 | 0.5490 | 1.0174 | 0.043* | |
C114 | −0.07991 (19) | 0.7526 (7) | 1.00123 (13) | 0.0452 (11) | |
H114 | −0.0856 | 0.8481 | 1.0242 | 0.054* | |
C115 | −0.03683 (18) | 0.7906 (8) | 0.97175 (13) | 0.0479 (11) | |
H115 | −0.0135 | 0.9116 | 0.9749 | 0.057* | |
C116 | −0.02788 (19) | 0.6531 (7) | 0.93795 (14) | 0.0449 (11) | |
H116 | 0.0019 | 0.6786 | 0.9184 | 0.054* | |
C117 | −0.06381 (17) | 0.4729 (6) | 0.93275 (12) | 0.0362 (9) | |
H117 | −0.0586 | 0.3814 | 0.9090 | 0.043* | |
O12 | −0.16021 (12) | 0.1581 (4) | 0.85792 (8) | 0.0409 (7) | |
O15 | −0.26457 (11) | 0.7900 (4) | 0.94108 (7) | 0.0331 (6) | |
N21 | 0.29507 (15) | 0.4846 (5) | 0.87566 (9) | 0.0348 (8) | |
C22 | 0.30010 (17) | 0.2900 (6) | 0.89185 (12) | 0.0348 (9) | |
C23 | 0.29341 (17) | 0.2573 (6) | 0.94162 (11) | 0.0358 (9) | |
H23 | 0.2670 | 0.1361 | 0.9448 | 0.043* | |
N24 | 0.26790 (14) | 0.4365 (5) | 0.96412 (10) | 0.0303 (7) | |
C25 | 0.26370 (16) | 0.6314 (6) | 0.94829 (11) | 0.0295 (9) | |
C26 | 0.27089 (17) | 0.6661 (6) | 0.89841 (10) | 0.0301 (9) | |
H26 | 0.2997 | 0.7814 | 0.8963 | 0.036* | |
C27 | 0.21073 (19) | 0.7328 (7) | 0.87301 (12) | 0.0459 (11) | |
H27A | 0.1808 | 0.6234 | 0.8755 | 0.055* | |
H27B | 0.1961 | 0.8581 | 0.8870 | 0.055* | |
C28 | 0.2173 (2) | 0.7755 (8) | 0.82307 (12) | 0.0520 (11) | |
H28A | 0.2413 | 0.9011 | 0.8203 | 0.062* | |
H28B | 0.1775 | 0.7995 | 0.8073 | 0.062* | |
C29 | 0.2479 (2) | 0.5920 (8) | 0.80068 (12) | 0.0520 (12) | |
H29A | 0.2204 | 0.4736 | 0.7981 | 0.062* | |
H29B | 0.2567 | 0.6318 | 0.7703 | 0.062* | |
C210 | 0.3064 (2) | 0.5295 (7) | 0.82815 (11) | 0.0491 (12) | |
H21A | 0.3231 | 0.4063 | 0.8148 | 0.059* | |
H21B | 0.3358 | 0.6417 | 0.8275 | 0.059* | |
C211 | 0.35748 (18) | 0.2066 (6) | 0.96520 (13) | 0.0415 (10) | |
H21C | 0.3544 | 0.1856 | 0.9974 | 0.050* | |
H21D | 0.3718 | 0.0771 | 0.9529 | 0.050* | |
C212 | 0.40331 (17) | 0.3767 (6) | 0.95916 (12) | 0.0357 (9) | |
C213 | 0.41134 (18) | 0.5452 (7) | 0.98971 (13) | 0.0431 (11) | |
H213 | 0.3894 | 0.5476 | 1.0150 | 0.052* | |
C214 | 0.45009 (18) | 0.7039 (7) | 0.98330 (15) | 0.0496 (12) | |
H214 | 0.4556 | 0.8099 | 1.0048 | 0.060* | |
C215 | 0.4813 (2) | 0.7095 (8) | 0.94532 (15) | 0.0545 (12) | |
H215 | 0.5065 | 0.8219 | 0.9403 | 0.065* | |
C216 | 0.47507 (18) | 0.5480 (8) | 0.91497 (15) | 0.0504 (12) | |
H216 | 0.4969 | 0.5498 | 0.8896 | 0.061* | |
C217 | 0.43610 (18) | 0.3795 (7) | 0.92158 (13) | 0.0425 (10) | |
H217 | 0.4324 | 0.2703 | 0.9007 | 0.051* | |
O22 | 0.31394 (14) | 0.1389 (4) | 0.86910 (8) | 0.0468 (7) | |
O25 | 0.25042 (12) | 0.7827 (4) | 0.97130 (8) | 0.0419 (7) | |
N31 | 0.01837 (13) | −0.0103 (5) | 0.80175 (9) | 0.0286 (7) | |
C32 | 0.01465 (16) | −0.2023 (6) | 0.78399 (11) | 0.0320 (9) | |
C33 | 0.03689 (17) | −0.2353 (6) | 0.73809 (11) | 0.0346 (9) | |
H33 | 0.0618 | −0.3622 | 0.7392 | 0.042* | |
N34 | 0.07276 (13) | −0.0620 (5) | 0.72206 (11) | 0.0337 (8) | |
C35 | 0.07335 (17) | 0.1319 (7) | 0.73811 (13) | 0.0355 (9) | |
C36 | 0.04788 (17) | 0.1700 (6) | 0.78317 (12) | 0.0333 (9) | |
H36 | 0.0175 | 0.2813 | 0.7786 | 0.040* | |
C37 | 0.09855 (19) | 0.2501 (7) | 0.81675 (13) | 0.0501 (11) | |
H37A | 0.1138 | 0.3810 | 0.8058 | 0.060* | |
H37B | 0.1317 | 0.1501 | 0.8191 | 0.060* | |
C38 | 0.0763 (2) | 0.2841 (8) | 0.86376 (13) | 0.0578 (12) | |
H38A | 0.1107 | 0.3182 | 0.8852 | 0.069* | |
H38B | 0.0486 | 0.4020 | 0.8624 | 0.069* | |
C39 | 0.04443 (19) | 0.0939 (7) | 0.88052 (12) | 0.0452 (11) | |
H39A | 0.0278 | 0.1260 | 0.9090 | 0.054* | |
H39B | 0.0732 | −0.0199 | 0.8858 | 0.054* | |
C310 | −0.00622 (16) | 0.0289 (7) | 0.84539 (11) | 0.0352 (9) | |
H31A | −0.0256 | −0.0969 | 0.8554 | 0.042* | |
H31B | −0.0366 | 0.1385 | 0.8418 | 0.042* | |
C311 | −0.01982 (17) | −0.2709 (6) | 0.70407 (13) | 0.0391 (10) | |
H31C | −0.0066 | −0.3152 | 0.6752 | 0.047* | |
H31D | −0.0439 | −0.3831 | 0.7153 | 0.047* | |
C312 | −0.05872 (16) | −0.0815 (6) | 0.69664 (12) | 0.0327 (9) | |
C313 | −0.04975 (17) | 0.0589 (7) | 0.66217 (11) | 0.0368 (10) | |
H313 | −0.0204 | 0.0314 | 0.6424 | 0.044* | |
C314 | −0.08438 (17) | 0.2415 (7) | 0.65687 (12) | 0.0414 (10) | |
H314 | −0.0780 | 0.3334 | 0.6334 | 0.050* | |
C315 | −0.12875 (17) | 0.2883 (7) | 0.68645 (12) | 0.0404 (10) | |
H315 | −0.1515 | 0.4105 | 0.6833 | 0.049* | |
C316 | −0.13721 (17) | 0.1448 (7) | 0.72049 (13) | 0.0420 (11) | |
H316 | −0.1667 | 0.1706 | 0.7403 | 0.050* | |
C317 | −0.10342 (16) | −0.0330 (7) | 0.72566 (12) | 0.0353 (9) | |
H317 | −0.1102 | −0.1246 | 0.7491 | 0.042* | |
O32 | −0.00871 (12) | −0.3519 (4) | 0.80245 (9) | 0.0451 (7) | |
O35 | 0.09600 (12) | 0.2802 (5) | 0.71901 (9) | 0.0472 (7) | |
N41 | 0.14268 (17) | 0.4798 (5) | 0.54158 (10) | 0.0427 (9) | |
C42 | 0.1474 (2) | 0.2896 (7) | 0.55880 (12) | 0.0455 (11) | |
C43 | 0.13511 (18) | 0.2563 (6) | 0.60750 (12) | 0.0381 (10) | |
H43 | 0.1088 | 0.1335 | 0.6086 | 0.046* | |
N44 | 0.10430 (16) | 0.4312 (6) | 0.62625 (13) | 0.0458 (9) | |
C45 | 0.10235 (17) | 0.6251 (7) | 0.61046 (13) | 0.0382 (10) | |
C46 | 0.11788 (18) | 0.6616 (6) | 0.56288 (12) | 0.0377 (10) | |
H46 | 0.1481 | 0.7739 | 0.5635 | 0.045* | |
C47 | 0.0613 (2) | 0.7334 (9) | 0.53346 (18) | 0.0833 (18) | |
H47A | 0.0463 | 0.8620 | 0.5458 | 0.100* | |
H47B | 0.0298 | 0.6282 | 0.5342 | 0.100* | |
C48 | 0.0752 (3) | 0.7704 (10) | 0.48347 (15) | 0.107 (2) | |
H48A | 0.0375 | 0.7977 | 0.4649 | 0.129* | |
H48B | 0.1010 | 0.8925 | 0.4821 | 0.129* | |
C49 | 0.1065 (3) | 0.5826 (9) | 0.46458 (15) | 0.094 (2) | |
H49A | 0.0786 | 0.4656 | 0.4614 | 0.113* | |
H49B | 0.1188 | 0.6158 | 0.4348 | 0.113* | |
C410 | 0.1612 (2) | 0.5239 (7) | 0.49581 (12) | 0.0606 (14) | |
H41A | 0.1804 | 0.4012 | 0.4842 | 0.073* | |
H41B | 0.1904 | 0.6375 | 0.4974 | 0.073* | |
C411 | 0.19496 (19) | 0.2079 (7) | 0.63580 (12) | 0.0445 (11) | |
H41C | 0.1869 | 0.1772 | 0.6668 | 0.053* | |
H41D | 0.2135 | 0.0854 | 0.6236 | 0.053* | |
C412 | 0.2383 (2) | 0.3910 (7) | 0.63552 (13) | 0.0484 (11) | |
C413 | 0.2380 (2) | 0.5455 (8) | 0.66754 (17) | 0.0698 (15) | |
H413 | 0.2127 | 0.5331 | 0.6908 | 0.084* | |
C414 | 0.2749 (4) | 0.7205 (11) | 0.6657 (3) | 0.116 (3) | |
H414 | 0.2750 | 0.8251 | 0.6876 | 0.139* | |
C415 | 0.3115 (4) | 0.7337 (17) | 0.6304 (4) | 0.169 (7) | |
H415 | 0.3369 | 0.8489 | 0.6287 | 0.203* | |
C416 | 0.3115 (3) | 0.5898 (17) | 0.5993 (4) | 0.148 (5) | |
H416 | 0.3361 | 0.6064 | 0.5757 | 0.178* | |
C417 | 0.2758 (2) | 0.4127 (9) | 0.60053 (17) | 0.0686 (15) | |
H417 | 0.2769 | 0.3099 | 0.5784 | 0.082* | |
O42 | 0.16481 (18) | 0.1379 (5) | 0.53748 (9) | 0.0724 (11) | |
O45 | 0.08605 (13) | 0.7761 (5) | 0.63259 (10) | 0.0534 (8) | |
N51 | 0.54685 (14) | 0.9973 (5) | 0.79982 (9) | 0.0297 (7) | |
C52 | 0.54046 (16) | 0.8034 (6) | 0.78274 (11) | 0.0314 (9) | |
C53 | 0.54674 (17) | 0.7714 (6) | 0.73256 (11) | 0.0350 (9) | |
H53 | 0.5731 | 0.6497 | 0.7298 | 0.042* | |
N54 | 0.57468 (15) | 0.9463 (5) | 0.71134 (11) | 0.0356 (8) | |
C55 | 0.57920 (16) | 1.1377 (6) | 0.72726 (12) | 0.0300 (8) | |
C56 | 0.56963 (15) | 1.1772 (6) | 0.77658 (11) | 0.0269 (8) | |
H56 | 0.5398 | 1.2900 | 0.7776 | 0.032* | |
C57 | 0.62886 (16) | 1.2506 (6) | 0.80293 (11) | 0.0363 (9) | |
H57A | 0.6427 | 1.3777 | 0.7892 | 0.044* | |
H57B | 0.6599 | 1.1447 | 0.8009 | 0.044* | |
C58 | 0.62001 (18) | 1.2922 (8) | 0.85343 (11) | 0.0430 (10) | |
H58A | 0.6593 | 1.3175 | 0.8700 | 0.052* | |
H58B | 0.5955 | 1.4169 | 0.8557 | 0.052* | |
C59 | 0.58940 (18) | 1.1099 (7) | 0.87504 (12) | 0.0446 (10) | |
H59A | 0.6174 | 0.9930 | 0.8786 | 0.053* | |
H59B | 0.5789 | 1.1502 | 0.9050 | 0.053* | |
C510 | 0.53255 (17) | 1.0430 (6) | 0.84632 (11) | 0.0345 (9) | |
H51A | 0.5157 | 0.9194 | 0.8594 | 0.041* | |
H51B | 0.5025 | 1.1535 | 0.8458 | 0.041* | |
C511 | 0.48428 (18) | 0.7169 (6) | 0.70839 (12) | 0.0404 (10) | |
H51C | 0.4882 | 0.6930 | 0.6764 | 0.048* | |
H51D | 0.4694 | 0.5891 | 0.7211 | 0.048* | |
C512 | 0.43946 (17) | 0.8907 (6) | 0.71351 (11) | 0.0342 (9) | |
C513 | 0.40434 (17) | 0.8918 (7) | 0.75043 (12) | 0.0438 (11) | |
H513 | 0.4077 | 0.7808 | 0.7708 | 0.053* | |
C514 | 0.3651 (2) | 1.0517 (9) | 0.75742 (14) | 0.0564 (13) | |
H514 | 0.3422 | 1.0491 | 0.7822 | 0.068* | |
C515 | 0.3598 (2) | 1.2195 (8) | 0.72680 (15) | 0.0630 (15) | |
H515 | 0.3330 | 1.3281 | 0.7311 | 0.076* | |
C516 | 0.3948 (2) | 1.2231 (7) | 0.69007 (13) | 0.0521 (12) | |
H516 | 0.3922 | 1.3355 | 0.6700 | 0.063* | |
C517 | 0.43388 (18) | 1.0568 (7) | 0.68354 (12) | 0.0407 (10) | |
H517 | 0.4566 | 1.0577 | 0.6586 | 0.049* | |
O52 | 0.52535 (13) | 0.6539 (4) | 0.80549 (8) | 0.0442 (7) | |
O55 | 0.59400 (11) | 1.2887 (4) | 0.70393 (7) | 0.0374 (6) | |
N61 | 0.63307 (16) | 1.5006 (5) | 0.52701 (10) | 0.0417 (9) | |
C62 | 0.6388 (2) | 1.3085 (6) | 0.54377 (12) | 0.0399 (10) | |
C63 | 0.62485 (17) | 1.2716 (6) | 0.59232 (10) | 0.0334 (9) | |
H63 | 0.5997 | 1.1458 | 0.5932 | 0.040* | |
N64 | 0.59291 (13) | 1.4456 (5) | 0.61204 (10) | 0.0289 (7) | |
C65 | 0.58960 (17) | 1.6417 (6) | 0.59598 (11) | 0.0305 (9) | |
C66 | 0.6057 (2) | 1.6791 (6) | 0.54838 (11) | 0.0412 (10) | |
H66 | 0.6358 | 1.7920 | 0.5500 | 0.049* | |
C67 | 0.5504 (2) | 1.7574 (8) | 0.51850 (12) | 0.0595 (13) | |
H67A | 0.5181 | 1.6548 | 0.5185 | 0.071* | |
H67B | 0.5360 | 1.8863 | 0.5311 | 0.071* | |
C68 | 0.5648 (3) | 1.7964 (9) | 0.46969 (13) | 0.0777 (17) | |
H68A | 0.5274 | 1.8249 | 0.4510 | 0.093* | |
H68B | 0.5905 | 1.9190 | 0.4689 | 0.093* | |
C69 | 0.5967 (3) | 1.6107 (8) | 0.44989 (13) | 0.0708 (16) | |
H69A | 0.5686 | 1.4944 | 0.4457 | 0.085* | |
H69B | 0.6094 | 1.6484 | 0.4205 | 0.085* | |
C610 | 0.6515 (2) | 1.5452 (8) | 0.48114 (12) | 0.0605 (14) | |
H61A | 0.6696 | 1.4214 | 0.4691 | 0.073* | |
H61B | 0.6815 | 1.6561 | 0.4829 | 0.073* | |
C611 | 0.68619 (17) | 1.2310 (6) | 0.62093 (11) | 0.0346 (9) | |
H61C | 0.6782 | 1.1936 | 0.6516 | 0.042* | |
H61D | 0.7063 | 1.1133 | 0.6081 | 0.042* | |
C612 | 0.72766 (16) | 1.4161 (7) | 0.62273 (12) | 0.0359 (10) | |
C613 | 0.72413 (17) | 1.5683 (7) | 0.65572 (14) | 0.0414 (10) | |
H613 | 0.6962 | 1.5535 | 0.6772 | 0.050* | |
C614 | 0.7611 (2) | 1.7403 (8) | 0.65714 (16) | 0.0583 (13) | |
H614 | 0.7594 | 1.8382 | 0.6802 | 0.070* | |
C615 | 0.8011 (2) | 1.7688 (9) | 0.62438 (19) | 0.0697 (15) | |
H615 | 0.8250 | 1.8884 | 0.6245 | 0.084* | |
C616 | 0.80500 (19) | 1.6173 (10) | 0.59150 (18) | 0.0635 (15) | |
H616 | 0.8325 | 1.6336 | 0.5698 | 0.076* | |
C617 | 0.76855 (18) | 1.4424 (8) | 0.59059 (14) | 0.0497 (12) | |
H617 | 0.7715 | 1.3416 | 0.5682 | 0.060* | |
O62 | 0.65854 (16) | 1.1591 (5) | 0.52299 (9) | 0.0589 (9) | |
O65 | 0.57063 (11) | 1.7889 (4) | 0.61750 (8) | 0.0388 (6) | |
H14 | −0.2546 (19) | 0.457 (7) | 0.9612 (14) | 0.061 (15)* | |
H24 | 0.262 (2) | 0.412 (7) | 0.9929 (15) | 0.072 (15)* | |
H34 | 0.0930 (16) | −0.086 (6) | 0.6935 (12) | 0.043 (11)* | |
H44 | 0.0995 (15) | 0.418 (6) | 0.6525 (11) | 0.021 (10)* | |
H54 | 0.5730 (13) | 0.935 (5) | 0.6824 (11) | 0.015 (8)* | |
H64 | 0.5802 (16) | 1.415 (6) | 0.6415 (12) | 0.041 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N11 | 0.0336 (17) | 0.0269 (19) | 0.0173 (13) | 0.0006 (13) | 0.0063 (12) | −0.0015 (13) |
C12 | 0.030 (2) | 0.023 (2) | 0.0271 (17) | −0.0046 (17) | 0.0023 (15) | −0.0051 (18) |
C13 | 0.0276 (19) | 0.021 (2) | 0.0406 (19) | −0.0085 (17) | 0.0071 (15) | 0.0066 (18) |
N14 | 0.0359 (18) | 0.0274 (19) | 0.0166 (14) | 0.0040 (14) | 0.0103 (13) | 0.0020 (14) |
C15 | 0.0253 (19) | 0.023 (2) | 0.0186 (15) | −0.0022 (16) | 0.0007 (14) | −0.0020 (17) |
C16 | 0.0274 (19) | 0.0177 (19) | 0.0242 (16) | −0.0038 (14) | 0.0101 (14) | −0.0021 (14) |
C17 | 0.046 (2) | 0.030 (2) | 0.0202 (16) | 0.0072 (19) | 0.0102 (15) | 0.0038 (17) |
C18 | 0.061 (3) | 0.035 (2) | 0.0209 (16) | 0.006 (2) | 0.0087 (17) | 0.0076 (18) |
C19 | 0.049 (2) | 0.035 (2) | 0.0180 (16) | −0.0077 (18) | 0.0158 (16) | 0.0013 (16) |
C110 | 0.042 (2) | 0.038 (2) | 0.0243 (17) | −0.0003 (19) | 0.0162 (16) | −0.0009 (17) |
C111 | 0.041 (2) | 0.032 (3) | 0.0353 (19) | 0.0059 (18) | 0.0072 (17) | 0.0075 (18) |
C112 | 0.041 (2) | 0.027 (2) | 0.0250 (17) | 0.0083 (18) | −0.0049 (17) | 0.0048 (17) |
C113 | 0.046 (2) | 0.036 (3) | 0.0253 (18) | 0.006 (2) | −0.0058 (17) | 0.0080 (18) |
C114 | 0.057 (3) | 0.031 (3) | 0.043 (2) | 0.008 (2) | −0.021 (2) | −0.003 (2) |
C115 | 0.043 (3) | 0.042 (3) | 0.054 (2) | −0.009 (2) | −0.025 (2) | 0.000 (2) |
C116 | 0.044 (3) | 0.042 (3) | 0.047 (2) | −0.003 (2) | −0.0067 (19) | 0.008 (2) |
C117 | 0.039 (2) | 0.037 (2) | 0.0311 (19) | 0.0028 (18) | −0.0020 (17) | 0.0055 (18) |
O12 | 0.0527 (17) | 0.0271 (17) | 0.0448 (15) | 0.0018 (13) | 0.0152 (13) | −0.0057 (13) |
O15 | 0.0523 (16) | 0.0254 (15) | 0.0233 (11) | 0.0076 (13) | 0.0123 (11) | −0.0063 (12) |
N21 | 0.058 (2) | 0.028 (2) | 0.0207 (14) | −0.0016 (15) | 0.0147 (15) | 0.0016 (14) |
C22 | 0.052 (2) | 0.016 (2) | 0.0375 (19) | −0.0100 (19) | 0.0129 (18) | −0.0058 (19) |
C23 | 0.046 (2) | 0.029 (2) | 0.0350 (19) | 0.0035 (19) | 0.0157 (17) | 0.0021 (19) |
N24 | 0.0455 (19) | 0.0272 (19) | 0.0203 (14) | 0.0005 (15) | 0.0143 (14) | 0.0033 (15) |
C25 | 0.043 (2) | 0.024 (2) | 0.0236 (17) | −0.0101 (18) | 0.0160 (16) | −0.0018 (18) |
C26 | 0.048 (2) | 0.020 (2) | 0.0234 (17) | −0.0043 (17) | 0.0125 (16) | 0.0004 (16) |
C27 | 0.060 (3) | 0.042 (3) | 0.036 (2) | −0.002 (2) | 0.0054 (19) | −0.0008 (19) |
C28 | 0.067 (3) | 0.051 (3) | 0.035 (2) | −0.002 (3) | −0.010 (2) | 0.008 (2) |
C29 | 0.080 (3) | 0.051 (3) | 0.0240 (19) | −0.016 (3) | 0.002 (2) | −0.002 (2) |
C210 | 0.084 (3) | 0.043 (3) | 0.0230 (19) | −0.013 (2) | 0.023 (2) | 0.0018 (19) |
C211 | 0.060 (3) | 0.028 (2) | 0.039 (2) | 0.009 (2) | 0.017 (2) | 0.0040 (18) |
C212 | 0.039 (2) | 0.035 (2) | 0.035 (2) | 0.0063 (18) | 0.0116 (17) | 0.0075 (18) |
C213 | 0.046 (2) | 0.049 (3) | 0.036 (2) | 0.013 (2) | 0.0130 (19) | −0.005 (2) |
C214 | 0.038 (2) | 0.052 (3) | 0.060 (3) | 0.007 (2) | 0.006 (2) | −0.013 (2) |
C215 | 0.053 (3) | 0.050 (3) | 0.061 (3) | −0.004 (2) | 0.009 (2) | 0.005 (2) |
C216 | 0.037 (2) | 0.058 (3) | 0.059 (3) | −0.007 (2) | 0.022 (2) | 0.006 (3) |
C217 | 0.047 (2) | 0.038 (3) | 0.045 (2) | 0.008 (2) | 0.016 (2) | −0.0025 (19) |
O22 | 0.079 (2) | 0.0249 (17) | 0.0393 (14) | −0.0095 (15) | 0.0217 (14) | −0.0061 (14) |
O25 | 0.0658 (19) | 0.0308 (16) | 0.0323 (12) | −0.0026 (15) | 0.0222 (13) | −0.0038 (14) |
N31 | 0.0276 (16) | 0.028 (2) | 0.0316 (15) | −0.0001 (13) | 0.0127 (13) | 0.0003 (14) |
C32 | 0.038 (2) | 0.021 (2) | 0.0390 (19) | 0.0016 (18) | 0.0145 (17) | 0.0040 (19) |
C33 | 0.044 (2) | 0.025 (2) | 0.0375 (19) | −0.0019 (18) | 0.0192 (17) | 0.0098 (19) |
N34 | 0.0303 (17) | 0.026 (2) | 0.0472 (19) | 0.0038 (14) | 0.0173 (15) | 0.0011 (16) |
C35 | 0.036 (2) | 0.027 (2) | 0.046 (2) | 0.0055 (18) | 0.0205 (18) | 0.001 (2) |
C36 | 0.041 (2) | 0.022 (2) | 0.039 (2) | 0.0016 (17) | 0.0133 (17) | 0.0004 (17) |
C37 | 0.050 (3) | 0.042 (3) | 0.058 (2) | −0.016 (2) | 0.007 (2) | 0.004 (2) |
C38 | 0.069 (3) | 0.048 (3) | 0.054 (2) | −0.015 (3) | −0.008 (2) | −0.007 (3) |
C39 | 0.054 (3) | 0.041 (3) | 0.038 (2) | −0.003 (2) | −0.0073 (19) | −0.001 (2) |
C310 | 0.036 (2) | 0.038 (2) | 0.0330 (19) | −0.0001 (18) | 0.0102 (17) | 0.0001 (18) |
C311 | 0.042 (2) | 0.030 (2) | 0.047 (2) | −0.0076 (19) | 0.0128 (19) | −0.0076 (19) |
C312 | 0.031 (2) | 0.034 (2) | 0.0334 (19) | −0.0048 (18) | 0.0032 (16) | −0.0045 (18) |
C313 | 0.039 (2) | 0.048 (3) | 0.0257 (18) | −0.005 (2) | 0.0100 (16) | −0.0024 (18) |
C314 | 0.047 (2) | 0.048 (3) | 0.0271 (18) | −0.004 (2) | −0.0050 (17) | 0.0035 (19) |
C315 | 0.039 (2) | 0.038 (2) | 0.044 (2) | 0.005 (2) | −0.0006 (18) | −0.012 (2) |
C316 | 0.029 (2) | 0.056 (3) | 0.041 (2) | 0.005 (2) | 0.0072 (18) | −0.010 (2) |
C317 | 0.036 (2) | 0.042 (3) | 0.0290 (18) | −0.0082 (19) | 0.0101 (17) | −0.0039 (18) |
O32 | 0.0569 (18) | 0.0293 (18) | 0.0527 (16) | −0.0037 (14) | 0.0244 (14) | 0.0087 (14) |
O35 | 0.0563 (18) | 0.0285 (16) | 0.0619 (16) | −0.0023 (14) | 0.0329 (14) | 0.0032 (15) |
N41 | 0.067 (2) | 0.030 (2) | 0.0298 (17) | −0.0014 (17) | 0.0001 (16) | −0.0032 (16) |
C42 | 0.069 (3) | 0.032 (3) | 0.035 (2) | −0.002 (2) | 0.001 (2) | −0.011 (2) |
C43 | 0.052 (3) | 0.014 (2) | 0.049 (2) | −0.0072 (18) | 0.0129 (19) | −0.0053 (19) |
N44 | 0.057 (2) | 0.032 (2) | 0.053 (2) | −0.0024 (18) | 0.0297 (19) | −0.0016 (19) |
C45 | 0.032 (2) | 0.029 (2) | 0.056 (2) | 0.0019 (18) | 0.0108 (19) | −0.005 (2) |
C46 | 0.047 (2) | 0.028 (2) | 0.037 (2) | −0.0032 (19) | −0.0032 (18) | −0.0071 (18) |
C47 | 0.083 (4) | 0.057 (4) | 0.101 (4) | 0.019 (3) | −0.041 (3) | −0.015 (3) |
C48 | 0.184 (7) | 0.081 (5) | 0.046 (3) | 0.043 (5) | −0.049 (4) | −0.005 (3) |
C49 | 0.165 (6) | 0.064 (4) | 0.043 (3) | 0.019 (4) | −0.044 (3) | −0.013 (3) |
C410 | 0.117 (4) | 0.039 (3) | 0.025 (2) | 0.003 (3) | 0.002 (2) | −0.0079 (19) |
C411 | 0.071 (3) | 0.031 (2) | 0.035 (2) | 0.009 (2) | 0.022 (2) | 0.0112 (18) |
C412 | 0.058 (3) | 0.051 (3) | 0.035 (2) | 0.008 (2) | −0.006 (2) | 0.020 (2) |
C413 | 0.084 (4) | 0.055 (3) | 0.062 (3) | −0.010 (3) | −0.036 (3) | 0.019 (3) |
C414 | 0.151 (7) | 0.056 (4) | 0.120 (6) | −0.025 (5) | −0.102 (5) | 0.017 (4) |
C415 | 0.081 (6) | 0.116 (9) | 0.287 (17) | −0.046 (7) | −0.112 (9) | 0.116 (10) |
C416 | 0.048 (4) | 0.182 (11) | 0.215 (11) | 0.001 (6) | 0.009 (6) | 0.162 (10) |
C417 | 0.047 (3) | 0.081 (4) | 0.079 (3) | 0.008 (3) | 0.014 (3) | 0.041 (3) |
O42 | 0.142 (3) | 0.033 (2) | 0.0448 (17) | 0.006 (2) | 0.0237 (19) | −0.0101 (16) |
O45 | 0.066 (2) | 0.0289 (17) | 0.0708 (18) | 0.0030 (16) | 0.0346 (16) | −0.0087 (16) |
N51 | 0.0410 (18) | 0.0219 (18) | 0.0279 (15) | 0.0000 (14) | 0.0117 (14) | 0.0024 (14) |
C52 | 0.030 (2) | 0.032 (2) | 0.0329 (18) | 0.0034 (18) | 0.0053 (16) | 0.0058 (19) |
C53 | 0.048 (2) | 0.017 (2) | 0.0417 (19) | 0.0066 (18) | 0.0178 (18) | 0.0043 (18) |
N54 | 0.050 (2) | 0.028 (2) | 0.0324 (18) | 0.0020 (15) | 0.0209 (16) | 0.0022 (16) |
C55 | 0.030 (2) | 0.022 (2) | 0.039 (2) | 0.0029 (17) | 0.0113 (16) | 0.0025 (19) |
C56 | 0.0253 (19) | 0.023 (2) | 0.0323 (18) | 0.0016 (15) | 0.0036 (15) | 0.0069 (16) |
C57 | 0.029 (2) | 0.037 (2) | 0.043 (2) | 0.0009 (18) | 0.0045 (16) | 0.005 (2) |
C58 | 0.041 (2) | 0.056 (3) | 0.0314 (18) | −0.006 (2) | −0.0014 (17) | 0.007 (2) |
C59 | 0.054 (3) | 0.046 (3) | 0.0342 (19) | 0.012 (2) | 0.0035 (19) | 0.004 (2) |
C510 | 0.046 (2) | 0.033 (2) | 0.0270 (18) | −0.0071 (19) | 0.0145 (17) | 0.0019 (17) |
C511 | 0.053 (3) | 0.033 (2) | 0.038 (2) | −0.006 (2) | 0.0176 (19) | −0.0031 (18) |
C512 | 0.038 (2) | 0.037 (2) | 0.0272 (18) | −0.0061 (19) | −0.0015 (17) | −0.0029 (18) |
C513 | 0.043 (2) | 0.055 (3) | 0.033 (2) | 0.001 (2) | 0.0069 (18) | 0.000 (2) |
C514 | 0.050 (3) | 0.081 (4) | 0.039 (2) | 0.014 (3) | 0.005 (2) | −0.007 (3) |
C515 | 0.055 (3) | 0.073 (4) | 0.058 (3) | 0.031 (3) | −0.014 (2) | −0.021 (3) |
C516 | 0.068 (3) | 0.048 (3) | 0.034 (2) | 0.007 (2) | −0.027 (2) | −0.003 (2) |
C517 | 0.053 (3) | 0.044 (3) | 0.0235 (18) | 0.003 (2) | −0.0071 (18) | −0.0014 (19) |
O52 | 0.0659 (19) | 0.0272 (17) | 0.0411 (14) | −0.0045 (14) | 0.0143 (14) | 0.0114 (13) |
O55 | 0.0509 (16) | 0.0302 (16) | 0.0335 (12) | −0.0017 (14) | 0.0170 (12) | 0.0064 (13) |
N61 | 0.067 (2) | 0.032 (2) | 0.0253 (16) | 0.0008 (17) | 0.0017 (16) | 0.0001 (15) |
C62 | 0.072 (3) | 0.018 (2) | 0.0308 (19) | −0.008 (2) | 0.0083 (19) | −0.0063 (19) |
C63 | 0.055 (2) | 0.021 (2) | 0.0234 (16) | 0.0068 (19) | −0.0004 (16) | −0.0079 (18) |
N64 | 0.0312 (17) | 0.0276 (19) | 0.0272 (15) | −0.0035 (14) | −0.0010 (13) | 0.0018 (15) |
C65 | 0.037 (2) | 0.029 (2) | 0.0230 (17) | −0.0081 (18) | −0.0089 (16) | −0.0002 (18) |
C66 | 0.071 (3) | 0.027 (2) | 0.0231 (18) | −0.003 (2) | −0.0095 (18) | 0.0013 (17) |
C67 | 0.087 (3) | 0.048 (3) | 0.038 (2) | 0.013 (3) | −0.025 (2) | −0.007 (2) |
C68 | 0.130 (5) | 0.054 (3) | 0.041 (2) | 0.007 (3) | −0.035 (3) | 0.001 (3) |
C69 | 0.127 (5) | 0.054 (3) | 0.028 (2) | −0.017 (3) | −0.015 (3) | 0.001 (2) |
C610 | 0.105 (4) | 0.056 (3) | 0.0213 (19) | −0.016 (3) | 0.010 (2) | 0.003 (2) |
C611 | 0.049 (2) | 0.026 (2) | 0.0296 (18) | 0.0122 (18) | 0.0102 (17) | 0.0094 (17) |
C612 | 0.030 (2) | 0.043 (3) | 0.035 (2) | 0.0088 (19) | 0.0088 (17) | 0.020 (2) |
C613 | 0.032 (2) | 0.040 (3) | 0.052 (2) | 0.0085 (19) | 0.0002 (19) | 0.003 (2) |
C614 | 0.048 (3) | 0.049 (3) | 0.074 (3) | −0.006 (2) | −0.016 (2) | 0.012 (3) |
C615 | 0.051 (3) | 0.049 (3) | 0.106 (4) | 0.001 (3) | −0.012 (3) | 0.040 (4) |
C616 | 0.034 (3) | 0.074 (4) | 0.084 (3) | 0.001 (3) | 0.014 (2) | 0.049 (3) |
C617 | 0.044 (3) | 0.056 (3) | 0.052 (2) | 0.014 (2) | 0.017 (2) | 0.021 (2) |
O62 | 0.111 (3) | 0.0301 (19) | 0.0383 (15) | −0.0023 (17) | 0.0189 (16) | −0.0095 (14) |
O65 | 0.0482 (16) | 0.0299 (16) | 0.0381 (13) | 0.0007 (14) | 0.0030 (12) | 0.0001 (14) |
N11—C12 | 1.334 (5) | N41—C42 | 1.319 (5) |
N11—C110 | 1.467 (4) | N41—C46 | 1.454 (5) |
N11—C16 | 1.472 (4) | N41—C410 | 1.478 (5) |
C12—O12 | 1.230 (4) | C42—O42 | 1.237 (5) |
C12—C13 | 1.504 (4) | C42—C43 | 1.505 (5) |
C13—N14 | 1.454 (5) | C43—N44 | 1.447 (5) |
C13—C111 | 1.533 (5) | C43—C411 | 1.531 (5) |
C13—H13 | 0.9800 | C43—H43 | 0.9800 |
N14—C15 | 1.338 (5) | N44—C45 | 1.324 (5) |
N14—H14 | 0.79 (4) | N44—H44 | 0.80 (3) |
C15—O15 | 1.238 (4) | C45—O45 | 1.239 (5) |
C15—C16 | 1.507 (4) | C45—C46 | 1.497 (5) |
C16—C17 | 1.519 (5) | C46—C47 | 1.529 (6) |
C16—H16 | 0.9800 | C46—H46 | 0.9800 |
C17—C18 | 1.531 (4) | C47—C48 | 1.556 (7) |
C17—H17A | 0.9700 | C47—H47A | 0.9700 |
C17—H17B | 0.9700 | C47—H47B | 0.9700 |
C18—C19 | 1.522 (5) | C48—C49 | 1.519 (7) |
C18—H18A | 0.9700 | C48—H48A | 0.9700 |
C18—H18B | 0.9700 | C48—H48B | 0.9700 |
C19—C110 | 1.505 (5) | C49—C410 | 1.501 (7) |
C19—H19A | 0.9700 | C49—H49A | 0.9700 |
C19—H19B | 0.9700 | C49—H49B | 0.9700 |
C110—H11A | 0.9700 | C410—H41A | 0.9700 |
C110—H11B | 0.9700 | C410—H41B | 0.9700 |
C111—C112 | 1.513 (5) | C411—C412 | 1.515 (6) |
C111—H11C | 0.9700 | C411—H41C | 0.9700 |
C111—H11D | 0.9700 | C411—H41D | 0.9700 |
C112—C113 | 1.397 (5) | C412—C413 | 1.369 (7) |
C112—C117 | 1.397 (5) | C412—C417 | 1.391 (6) |
C113—C114 | 1.385 (6) | C413—C414 | 1.389 (8) |
C113—H113 | 0.9300 | C413—H413 | 0.9300 |
C114—C115 | 1.371 (6) | C414—C415 | 1.383 (13) |
C114—H114 | 0.9300 | C414—H414 | 0.9300 |
C115—C116 | 1.360 (6) | C415—C416 | 1.300 (15) |
C115—H115 | 0.9300 | C415—H415 | 0.9300 |
C116—C117 | 1.401 (6) | C416—C417 | 1.383 (10) |
C116—H116 | 0.9300 | C416—H416 | 0.9300 |
C117—H117 | 0.9300 | C417—H417 | 0.9300 |
N21—C22 | 1.335 (5) | N51—C52 | 1.342 (5) |
N21—C26 | 1.467 (4) | N51—C56 | 1.454 (4) |
N21—C210 | 1.478 (4) | N51—C510 | 1.469 (4) |
C22—O22 | 1.232 (4) | C52—O52 | 1.233 (4) |
C22—C23 | 1.507 (5) | C52—C53 | 1.517 (5) |
C23—N24 | 1.464 (5) | C53—N54 | 1.448 (5) |
C23—C211 | 1.555 (5) | C53—C511 | 1.536 (5) |
C23—H23 | 0.9800 | C53—H53 | 0.9800 |
N24—C25 | 1.332 (5) | N54—C55 | 1.312 (5) |
N24—H24 | 0.89 (4) | N54—H54 | 0.86 (3) |
C25—O25 | 1.234 (4) | C55—O55 | 1.249 (4) |
C25—C26 | 1.515 (4) | C55—C56 | 1.514 (5) |
C26—C27 | 1.527 (5) | C56—C57 | 1.535 (5) |
C26—H26 | 0.9800 | C56—H56 | 0.9800 |
C27—C28 | 1.522 (5) | C57—C58 | 1.547 (5) |
C27—H27A | 0.9700 | C57—H57A | 0.9700 |
C27—H27B | 0.9700 | C57—H57B | 0.9700 |
C28—C29 | 1.535 (6) | C58—C59 | 1.518 (6) |
C28—H28A | 0.9700 | C58—H58A | 0.9700 |
C28—H28B | 0.9700 | C58—H58B | 0.9700 |
C29—C210 | 1.516 (6) | C59—C510 | 1.513 (5) |
C29—H29A | 0.9700 | C59—H59A | 0.9700 |
C29—H29B | 0.9700 | C59—H59B | 0.9700 |
C210—H21A | 0.9700 | C510—H51A | 0.9700 |
C210—H21B | 0.9700 | C510—H51B | 0.9700 |
C211—C212 | 1.509 (6) | C511—C512 | 1.506 (5) |
C211—H21C | 0.9700 | C511—H51C | 0.9700 |
C211—H21D | 0.9700 | C511—H51D | 0.9700 |
C212—C217 | 1.382 (5) | C512—C517 | 1.382 (5) |
C212—C213 | 1.407 (6) | C512—C513 | 1.397 (5) |
C213—C214 | 1.353 (6) | C513—C514 | 1.369 (6) |
C213—H213 | 0.9300 | C513—H513 | 0.9300 |
C214—C215 | 1.372 (6) | C514—C515 | 1.402 (7) |
C214—H214 | 0.9300 | C514—H514 | 0.9300 |
C215—C216 | 1.367 (6) | C515—C516 | 1.390 (6) |
C215—H215 | 0.9300 | C515—H515 | 0.9300 |
C216—C217 | 1.405 (6) | C516—C517 | 1.395 (6) |
C216—H216 | 0.9300 | C516—H516 | 0.9300 |
C217—H217 | 0.9300 | C517—H517 | 0.9300 |
N31—C32 | 1.335 (5) | N61—C62 | 1.327 (5) |
N31—C36 | 1.457 (4) | N61—C66 | 1.462 (5) |
N31—C310 | 1.467 (4) | N61—C610 | 1.480 (5) |
C32—O32 | 1.238 (4) | C62—O62 | 1.238 (5) |
C32—C33 | 1.501 (5) | C62—C63 | 1.514 (5) |
C33—N34 | 1.466 (5) | C63—N64 | 1.467 (5) |
C33—C311 | 1.551 (5) | C63—C611 | 1.553 (5) |
C33—H33 | 0.9800 | C63—H63 | 0.9800 |
N34—C35 | 1.328 (5) | N64—C65 | 1.341 (5) |
N34—H34 | 1.00 (4) | N64—H64 | 0.96 (4) |
C35—O35 | 1.234 (5) | C65—O65 | 1.232 (4) |
C35—C36 | 1.514 (5) | C65—C66 | 1.503 (5) |
C36—C37 | 1.516 (5) | C66—C67 | 1.527 (6) |
C36—H36 | 0.9800 | C66—H66 | 0.9800 |
C37—C38 | 1.533 (5) | C67—C68 | 1.527 (6) |
C37—H37A | 0.9700 | C67—H67A | 0.9700 |
C37—H37B | 0.9700 | C67—H67B | 0.9700 |
C38—C39 | 1.512 (6) | C68—C69 | 1.525 (7) |
C38—H38A | 0.9700 | C68—H68A | 0.9700 |
C38—H38B | 0.9700 | C68—H68B | 0.9700 |
C39—C310 | 1.515 (5) | C69—C610 | 1.514 (7) |
C39—H39A | 0.9700 | C69—H69A | 0.9700 |
C39—H39B | 0.9700 | C69—H69B | 0.9700 |
C310—H31A | 0.9700 | C610—H61A | 0.9700 |
C310—H31B | 0.9700 | C610—H61B | 0.9700 |
C311—C312 | 1.490 (5) | C611—C612 | 1.496 (6) |
C311—H31C | 0.9700 | C611—H61C | 0.9700 |
C311—H31D | 0.9700 | C611—H61D | 0.9700 |
C312—C313 | 1.387 (5) | C612—C617 | 1.381 (5) |
C312—C317 | 1.402 (5) | C612—C613 | 1.386 (6) |
C313—C314 | 1.397 (6) | C613—C614 | 1.369 (6) |
C313—H313 | 0.9300 | C613—H613 | 0.9300 |
C314—C315 | 1.406 (5) | C614—C615 | 1.382 (7) |
C314—H314 | 0.9300 | C614—H614 | 0.9300 |
C315—C316 | 1.388 (6) | C615—C616 | 1.381 (7) |
C315—H315 | 0.9300 | C615—H615 | 0.9300 |
C316—C317 | 1.361 (6) | C616—C617 | 1.378 (7) |
C316—H316 | 0.9300 | C616—H616 | 0.9300 |
C317—H317 | 0.9300 | C617—H617 | 0.9300 |
C12—N11—C110 | 120.2 (3) | C42—N41—C46 | 126.2 (3) |
C12—N11—C16 | 125.8 (3) | C42—N41—C410 | 120.7 (3) |
C110—N11—C16 | 113.9 (3) | C46—N41—C410 | 113.1 (3) |
O12—C12—N11 | 122.7 (3) | O42—C42—N41 | 122.9 (4) |
O12—C12—C13 | 118.4 (3) | O42—C42—C43 | 118.0 (4) |
N11—C12—C13 | 118.8 (3) | N41—C42—C43 | 119.0 (4) |
N14—C13—C12 | 113.7 (3) | N44—C43—C42 | 113.0 (4) |
N14—C13—C111 | 111.4 (3) | N44—C43—C411 | 111.1 (3) |
C12—C13—C111 | 110.2 (3) | C42—C43—C411 | 109.2 (3) |
N14—C13—H13 | 107.1 | N44—C43—H43 | 107.8 |
C12—C13—H13 | 107.1 | C42—C43—H43 | 107.8 |
C111—C13—H13 | 107.1 | C411—C43—H43 | 107.8 |
C15—N14—C13 | 125.8 (3) | C45—N44—C43 | 126.2 (3) |
C15—N14—H14 | 104 (4) | C45—N44—H44 | 116 (3) |
C13—N14—H14 | 128 (3) | C43—N44—H44 | 113 (3) |
O15—C15—N14 | 123.1 (3) | O45—C45—N44 | 123.1 (4) |
O15—C15—C16 | 118.8 (3) | O45—C45—C46 | 118.5 (4) |
N14—C15—C16 | 118.0 (3) | N44—C45—C46 | 118.3 (4) |
N11—C16—C15 | 114.6 (3) | N41—C46—C45 | 114.3 (3) |
N11—C16—C17 | 109.2 (3) | N41—C46—C47 | 108.4 (3) |
C15—C16—C17 | 110.0 (3) | C45—C46—C47 | 109.6 (4) |
N11—C16—H16 | 107.6 | N41—C46—H46 | 108.1 |
C15—C16—H16 | 107.6 | C45—C46—H46 | 108.1 |
C17—C16—H16 | 107.6 | C47—C46—H46 | 108.1 |
C16—C17—C18 | 112.8 (3) | C46—C47—C48 | 111.3 (5) |
C16—C17—H17A | 109.0 | C46—C47—H47A | 109.4 |
C18—C17—H17A | 109.0 | C48—C47—H47A | 109.4 |
C16—C17—H17B | 109.0 | C46—C47—H47B | 109.4 |
C18—C17—H17B | 109.0 | C48—C47—H47B | 109.4 |
H17A—C17—H17B | 107.8 | H47A—C47—H47B | 108.0 |
C19—C18—C17 | 110.7 (3) | C49—C48—C47 | 111.5 (5) |
C19—C18—H18A | 109.5 | C49—C48—H48A | 109.3 |
C17—C18—H18A | 109.5 | C47—C48—H48A | 109.3 |
C19—C18—H18B | 109.5 | C49—C48—H48B | 109.3 |
C17—C18—H18B | 109.5 | C47—C48—H48B | 109.3 |
H18A—C18—H18B | 108.1 | H48A—C48—H48B | 108.0 |
C110—C19—C18 | 110.1 (3) | C410—C49—C48 | 109.9 (4) |
C110—C19—H19A | 109.6 | C410—C49—H49A | 109.7 |
C18—C19—H19A | 109.6 | C48—C49—H49A | 109.7 |
C110—C19—H19B | 109.6 | C410—C49—H49B | 109.7 |
C18—C19—H19B | 109.6 | C48—C49—H49B | 109.7 |
H19A—C19—H19B | 108.2 | H49A—C49—H49B | 108.2 |
N11—C110—C19 | 109.8 (3) | N41—C410—C49 | 109.6 (4) |
N11—C110—H11A | 109.7 | N41—C410—H41A | 109.7 |
C19—C110—H11A | 109.7 | C49—C410—H41A | 109.7 |
N11—C110—H11B | 109.7 | N41—C410—H41B | 109.7 |
C19—C110—H11B | 109.7 | C49—C410—H41B | 109.7 |
H11A—C110—H11B | 108.2 | H41A—C410—H41B | 108.2 |
C112—C111—C13 | 111.3 (3) | C412—C411—C43 | 110.9 (3) |
C112—C111—H11C | 109.4 | C412—C411—H41C | 109.5 |
C13—C111—H11C | 109.4 | C43—C411—H41C | 109.5 |
C112—C111—H11D | 109.4 | C412—C411—H41D | 109.5 |
C13—C111—H11D | 109.4 | C43—C411—H41D | 109.5 |
H11C—C111—H11D | 108.0 | H41C—C411—H41D | 108.0 |
C113—C112—C117 | 117.7 (4) | C413—C412—C417 | 119.0 (5) |
C113—C112—C111 | 120.5 (3) | C413—C412—C411 | 120.7 (4) |
C117—C112—C111 | 121.8 (3) | C417—C412—C411 | 120.1 (5) |
C114—C113—C112 | 120.6 (4) | C412—C413—C414 | 121.0 (6) |
C114—C113—H113 | 119.7 | C412—C413—H413 | 119.5 |
C112—C113—H113 | 119.7 | C414—C413—H413 | 119.5 |
C115—C114—C113 | 120.6 (4) | C415—C414—C413 | 117.7 (8) |
C115—C114—H114 | 119.7 | C415—C414—H414 | 121.1 |
C113—C114—H114 | 119.7 | C413—C414—H414 | 121.1 |
C116—C115—C114 | 120.6 (4) | C416—C415—C414 | 121.9 (10) |
C116—C115—H115 | 119.7 | C416—C415—H415 | 119.1 |
C114—C115—H115 | 119.7 | C414—C415—H415 | 119.1 |
C115—C116—C117 | 119.6 (4) | C415—C416—C417 | 121.7 (10) |
C115—C116—H116 | 120.2 | C415—C416—H416 | 119.1 |
C117—C116—H116 | 120.2 | C417—C416—H416 | 119.1 |
C112—C117—C116 | 121.0 (4) | C416—C417—C412 | 118.7 (7) |
C112—C117—H117 | 119.5 | C416—C417—H417 | 120.6 |
C116—C117—H117 | 119.5 | C412—C417—H417 | 120.6 |
C22—N21—C26 | 126.5 (3) | C52—N51—C56 | 125.6 (3) |
C22—N21—C210 | 120.4 (3) | C52—N51—C510 | 120.8 (3) |
C26—N21—C210 | 112.5 (3) | C56—N51—C510 | 113.5 (3) |
O22—C22—N21 | 123.5 (3) | O52—C52—N51 | 122.4 (3) |
O22—C22—C23 | 118.4 (4) | O52—C52—C53 | 118.9 (4) |
N21—C22—C23 | 117.8 (3) | N51—C52—C53 | 118.5 (3) |
N24—C23—C22 | 114.3 (3) | N54—C53—C52 | 113.6 (3) |
N24—C23—C211 | 109.4 (3) | N54—C53—C511 | 112.0 (3) |
C22—C23—C211 | 107.5 (3) | C52—C53—C511 | 109.1 (3) |
N24—C23—H23 | 108.5 | N54—C53—H53 | 107.3 |
C22—C23—H23 | 108.5 | C52—C53—H53 | 107.3 |
C211—C23—H23 | 108.5 | C511—C53—H53 | 107.3 |
C25—N24—C23 | 126.2 (3) | C55—N54—C53 | 125.9 (3) |
C25—N24—H24 | 120 (3) | C55—N54—H54 | 115 (2) |
C23—N24—H24 | 113 (3) | C53—N54—H54 | 113 (2) |
O25—C25—N24 | 123.6 (3) | O55—C55—N54 | 122.6 (3) |
O25—C25—C26 | 118.3 (3) | O55—C55—C56 | 118.0 (3) |
N24—C25—C26 | 118.0 (3) | N54—C55—C56 | 119.3 (3) |
N21—C26—C25 | 113.9 (3) | N51—C56—C55 | 114.1 (3) |
N21—C26—C27 | 109.4 (3) | N51—C56—C57 | 108.6 (3) |
C25—C26—C27 | 110.8 (3) | C55—C56—C57 | 110.6 (3) |
N21—C26—H26 | 107.4 | N51—C56—H56 | 107.8 |
C25—C26—H26 | 107.4 | C55—C56—H56 | 107.8 |
C27—C26—H26 | 107.4 | C57—C56—H56 | 107.8 |
C28—C27—C26 | 111.8 (3) | C56—C57—C58 | 111.4 (3) |
C28—C27—H27A | 109.3 | C56—C57—H57A | 109.3 |
C26—C27—H27A | 109.3 | C58—C57—H57A | 109.3 |
C28—C27—H27B | 109.3 | C56—C57—H57B | 109.3 |
C26—C27—H27B | 109.3 | C58—C57—H57B | 109.3 |
H27A—C27—H27B | 107.9 | H57A—C57—H57B | 108.0 |
C27—C28—C29 | 111.5 (4) | C59—C58—C57 | 112.0 (4) |
C27—C28—H28A | 109.3 | C59—C58—H58A | 109.2 |
C29—C28—H28A | 109.3 | C57—C58—H58A | 109.2 |
C27—C28—H28B | 109.3 | C59—C58—H58B | 109.2 |
C29—C28—H28B | 109.3 | C57—C58—H58B | 109.2 |
H28A—C28—H28B | 108.0 | H58A—C58—H58B | 107.9 |
C210—C29—C28 | 111.0 (3) | C510—C59—C58 | 111.1 (3) |
C210—C29—H29A | 109.4 | C510—C59—H59A | 109.4 |
C28—C29—H29A | 109.4 | C58—C59—H59A | 109.4 |
C210—C29—H29B | 109.4 | C510—C59—H59B | 109.4 |
C28—C29—H29B | 109.4 | C58—C59—H59B | 109.4 |
H29A—C29—H29B | 108.0 | H59A—C59—H59B | 108.0 |
N21—C210—C29 | 110.5 (3) | N51—C510—C59 | 110.1 (3) |
N21—C210—H21A | 109.5 | N51—C510—H51A | 109.7 |
C29—C210—H21A | 109.5 | C59—C510—H51A | 109.7 |
N21—C210—H21B | 109.5 | N51—C510—H51B | 109.7 |
C29—C210—H21B | 109.5 | C59—C510—H51B | 109.7 |
H21A—C210—H21B | 108.1 | H51A—C510—H51B | 108.2 |
C212—C211—C23 | 113.0 (3) | C512—C511—C53 | 111.0 (3) |
C212—C211—H21C | 109.0 | C512—C511—H51C | 109.4 |
C23—C211—H21C | 109.0 | C53—C511—H51C | 109.4 |
C212—C211—H21D | 109.0 | C512—C511—H51D | 109.4 |
C23—C211—H21D | 109.0 | C53—C511—H51D | 109.4 |
H21C—C211—H21D | 107.8 | H51C—C511—H51D | 108.0 |
C217—C212—C213 | 117.5 (4) | C517—C512—C513 | 118.3 (4) |
C217—C212—C211 | 120.8 (4) | C517—C512—C511 | 121.6 (3) |
C213—C212—C211 | 121.5 (3) | C513—C512—C511 | 120.0 (4) |
C214—C213—C212 | 121.9 (4) | C514—C513—C512 | 121.8 (4) |
C214—C213—H213 | 119.0 | C514—C513—H513 | 119.1 |
C212—C213—H213 | 119.0 | C512—C513—H513 | 119.1 |
C213—C214—C215 | 120.5 (4) | C513—C514—C515 | 119.4 (4) |
C213—C214—H214 | 119.8 | C513—C514—H514 | 120.3 |
C215—C214—H214 | 119.8 | C515—C514—H514 | 120.3 |
C216—C215—C214 | 119.3 (4) | C516—C515—C514 | 119.9 (4) |
C216—C215—H215 | 120.3 | C516—C515—H515 | 120.1 |
C214—C215—H215 | 120.3 | C514—C515—H515 | 120.1 |
C215—C216—C217 | 121.0 (4) | C515—C516—C517 | 119.4 (4) |
C215—C216—H216 | 119.5 | C515—C516—H516 | 120.3 |
C217—C216—H216 | 119.5 | C517—C516—H516 | 120.3 |
C212—C217—C216 | 119.7 (4) | C512—C517—C516 | 121.1 (4) |
C212—C217—H217 | 120.1 | C512—C517—H517 | 119.4 |
C216—C217—H217 | 120.1 | C516—C517—H517 | 119.4 |
C32—N31—C36 | 126.4 (3) | C62—N61—C66 | 126.2 (3) |
C32—N31—C310 | 119.2 (3) | C62—N61—C610 | 119.8 (4) |
C36—N31—C310 | 114.3 (3) | C66—N61—C610 | 113.9 (3) |
O32—C32—N31 | 123.4 (3) | O62—C62—N61 | 123.7 (3) |
O32—C32—C33 | 118.4 (4) | O62—C62—C63 | 117.5 (4) |
N31—C32—C33 | 118.1 (3) | N61—C62—C63 | 118.6 (3) |
N34—C33—C32 | 114.7 (3) | N64—C63—C62 | 113.9 (3) |
N34—C33—C311 | 109.3 (3) | N64—C63—C611 | 109.8 (3) |
C32—C33—C311 | 107.1 (3) | C62—C63—C611 | 107.4 (3) |
N34—C33—H33 | 108.5 | N64—C63—H63 | 108.5 |
C32—C33—H33 | 108.5 | C62—C63—H63 | 108.5 |
C311—C33—H33 | 108.5 | C611—C63—H63 | 108.5 |
C35—N34—C33 | 125.3 (3) | C65—N64—C63 | 125.5 (3) |
C35—N34—H34 | 117 (2) | C65—N64—H64 | 120 (2) |
C33—N34—H34 | 117 (2) | C63—N64—H64 | 113 (2) |
O35—C35—N34 | 123.1 (3) | O65—C65—N64 | 122.8 (3) |
O35—C35—C36 | 118.6 (4) | O65—C65—C66 | 118.9 (3) |
N34—C35—C36 | 118.2 (3) | N64—C65—C66 | 118.1 (3) |
N31—C36—C35 | 114.8 (3) | N61—C66—C65 | 115.1 (3) |
N31—C36—C37 | 110.5 (3) | N61—C66—C67 | 110.3 (3) |
C35—C36—C37 | 108.6 (3) | C65—C66—C67 | 110.3 (4) |
N31—C36—H36 | 107.6 | N61—C66—H66 | 106.9 |
C35—C36—H36 | 107.6 | C65—C66—H66 | 106.9 |
C37—C36—H36 | 107.6 | C67—C66—H66 | 106.9 |
C36—C37—C38 | 111.3 (3) | C68—C67—C66 | 112.0 (4) |
C36—C37—H37A | 109.4 | C68—C67—H67A | 109.2 |
C38—C37—H37A | 109.4 | C66—C67—H67A | 109.2 |
C36—C37—H37B | 109.4 | C68—C67—H67B | 109.2 |
C38—C37—H37B | 109.4 | C66—C67—H67B | 109.2 |
H37A—C37—H37B | 108.0 | H67A—C67—H67B | 107.9 |
C39—C38—C37 | 112.4 (4) | C69—C68—C67 | 112.3 (4) |
C39—C38—H38A | 109.1 | C69—C68—H68A | 109.1 |
C37—C38—H38A | 109.1 | C67—C68—H68A | 109.1 |
C39—C38—H38B | 109.1 | C69—C68—H68B | 109.1 |
C37—C38—H38B | 109.1 | C67—C68—H68B | 109.1 |
H38A—C38—H38B | 107.9 | H68A—C68—H68B | 107.9 |
C38—C39—C310 | 109.5 (3) | C610—C69—C68 | 110.7 (4) |
C38—C39—H39A | 109.8 | C610—C69—H69A | 109.5 |
C310—C39—H39A | 109.8 | C68—C69—H69A | 109.5 |
C38—C39—H39B | 109.8 | C610—C69—H69B | 109.5 |
C310—C39—H39B | 109.8 | C68—C69—H69B | 109.5 |
H39A—C39—H39B | 108.2 | H69A—C69—H69B | 108.1 |
N31—C310—C39 | 109.9 (3) | N61—C610—C69 | 109.9 (4) |
N31—C310—H31A | 109.7 | N61—C610—H61A | 109.7 |
C39—C310—H31A | 109.7 | C69—C610—H61A | 109.7 |
N31—C310—H31B | 109.7 | N61—C610—H61B | 109.7 |
C39—C310—H31B | 109.7 | C69—C610—H61B | 109.7 |
H31A—C310—H31B | 108.2 | H61A—C610—H61B | 108.2 |
C312—C311—C33 | 113.4 (3) | C612—C611—C63 | 112.9 (3) |
C312—C311—H31C | 108.9 | C612—C611—H61C | 109.0 |
C33—C311—H31C | 108.9 | C63—C611—H61C | 109.0 |
C312—C311—H31D | 108.9 | C612—C611—H61D | 109.0 |
C33—C311—H31D | 108.9 | C63—C611—H61D | 109.0 |
H31C—C311—H31D | 107.7 | H61C—C611—H61D | 107.8 |
C313—C312—C317 | 117.6 (4) | C617—C612—C613 | 118.8 (4) |
C313—C312—C311 | 121.0 (3) | C617—C612—C611 | 120.7 (4) |
C317—C312—C311 | 121.3 (4) | C613—C612—C611 | 120.5 (3) |
C312—C313—C314 | 120.7 (3) | C614—C613—C612 | 120.9 (4) |
C312—C313—H313 | 119.7 | C614—C613—H613 | 119.5 |
C314—C313—H313 | 119.7 | C612—C613—H613 | 119.5 |
C313—C314—C315 | 121.0 (4) | C613—C614—C615 | 120.2 (5) |
C313—C314—H314 | 119.5 | C613—C614—H614 | 119.9 |
C315—C314—H314 | 119.5 | C615—C614—H614 | 119.9 |
C316—C315—C314 | 117.3 (4) | C616—C615—C614 | 119.1 (5) |
C316—C315—H315 | 121.3 | C616—C615—H615 | 120.4 |
C314—C315—H315 | 121.3 | C614—C615—H615 | 120.4 |
C317—C316—C315 | 121.7 (4) | C617—C616—C615 | 120.6 (4) |
C317—C316—H316 | 119.2 | C617—C616—H616 | 119.7 |
C315—C316—H316 | 119.2 | C615—C616—H616 | 119.7 |
C316—C317—C312 | 121.8 (4) | C616—C617—C612 | 120.3 (5) |
C316—C317—H317 | 119.1 | C616—C617—H617 | 119.9 |
C312—C317—H317 | 119.1 | C612—C617—H617 | 119.9 |
D—H···A | D—H | H···A | D···A | D—H···A |
N14—H14···O25i | 0.79 (4) | 2.28 (4) | 2.906 (4) | 137 (4) |
N24—H24···O15i | 0.89 (4) | 2.10 (5) | 2.964 (4) | 165 (4) |
N34—H34···O45ii | 1.00 (4) | 2.00 (4) | 2.881 (4) | 145 (3) |
N44—H44···O35 | 0.80 (3) | 2.16 (3) | 2.930 (5) | 162 (4) |
N54—H54···O65ii | 0.86 (3) | 2.13 (3) | 2.946 (4) | 159 (3) |
N64—H64···O55 | 0.96 (4) | 2.01 (4) | 2.895 (4) | 152 (3) |
Symmetry codes: (i) −x, y−1/2, −z+2; (ii) x, y−1, z. |
C16H20N2O2 | Z = 2 |
Mr = 272.34 | F(000) = 292 |
Triclinic, P1 | Dx = 1.304 Mg m−3 |
Hall symbol: P 1 | Mo Kα radiation, λ = 0.71070 Å |
a = 7.4277 (2) Å | Cell parameters from 10488 reflections |
b = 7.4388 (3) Å | θ = 1–27° |
c = 13.5369 (5) Å | µ = 0.09 mm−1 |
α = 90.176 (2)° | T = 150 K |
β = 79.737 (2)° | Irregular, colourless |
γ = 70.800 (2)° | 0.5 × 0.35 × 0.25 mm |
V = 693.52 (4) Å3 |
Nonius KappaCCD area detector diffractometer | 4906 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.070 |
Graphite monochromator | θmax = 27.2°, θmin = 2.9° |
Detector resolution: 9.091 pixels mm-1 | h = −9→9 |
φ and ω scans to fill the Ewald sphere | k = −9→9 |
11078 measured reflections | l = −17→15 |
5078 independent reflections |
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)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.101 | w = 1/[σ2(Fo2) + (0.0539P)2 + 0.1346P] where P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
5078 reflections | Δρmax = 0.28 e Å−3 |
363 parameters | Δρmin = −0.24 e Å−3 |
3 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.2 (9) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.6311 (2) | 0.2315 (2) | 0.08112 (11) | 0.0226 (3) | |
C2 | 0.6909 (2) | 0.0720 (2) | 0.02033 (13) | 0.0228 (3) | |
O2 | 0.59020 (18) | −0.0293 (2) | 0.01480 (10) | 0.0322 (3) | |
C3 | 0.8911 (2) | 0.0123 (2) | −0.04502 (13) | 0.0219 (3) | |
H3 | 0.8750 | −0.0082 | −0.1140 | 0.026* | |
N4 | 0.9873 (2) | 0.1559 (2) | −0.04707 (11) | 0.0227 (3) | |
C4 | 1.1665 (3) | 0.1208 (3) | −0.12202 (15) | 0.0293 (4) | |
H4A | 1.1761 | 0.2402 | −0.1443 | 0.044* | |
H4B | 1.1640 | 0.0436 | −0.1784 | 0.044* | |
H4C | 1.2764 | 0.0555 | −0.0923 | 0.044* | |
C5 | 0.9445 (2) | 0.2951 (2) | 0.02569 (13) | 0.0237 (3) | |
O5 | 1.0476 (2) | 0.39306 (19) | 0.03084 (11) | 0.0350 (3) | |
C6 | 0.7544 (2) | 0.3399 (2) | 0.10051 (13) | 0.0230 (3) | |
H6 | 0.6809 | 0.4744 | 0.0950 | 0.028* | |
C7 | 0.7881 (3) | 0.3218 (3) | 0.20922 (13) | 0.0267 (4) | |
H7A | 0.8645 | 0.1912 | 0.2179 | 0.032* | |
H7B | 0.8602 | 0.4036 | 0.2230 | 0.032* | |
C8 | 0.5947 (3) | 0.3783 (3) | 0.28314 (15) | 0.0341 (4) | |
H8A | 0.6188 | 0.3525 | 0.3507 | 0.041* | |
H8B | 0.5278 | 0.5142 | 0.2820 | 0.041* | |
C9 | 0.4668 (3) | 0.2697 (3) | 0.25712 (15) | 0.0350 (4) | |
H9A | 0.3411 | 0.3168 | 0.3016 | 0.042* | |
H9B | 0.5254 | 0.1355 | 0.2673 | 0.042* | |
C10 | 0.4398 (2) | 0.2920 (3) | 0.14862 (14) | 0.0294 (4) | |
H10A | 0.3650 | 0.2147 | 0.1323 | 0.035* | |
H10B | 0.3692 | 0.4242 | 0.1397 | 0.035* | |
C11 | 1.0179 (3) | −0.1816 (2) | −0.01458 (14) | 0.0254 (4) | |
H11A | 0.9570 | −0.2761 | −0.0234 | 0.030* | |
H11B | 1.1433 | −0.2212 | −0.0595 | 0.030* | |
C12 | 1.0488 (2) | −0.1780 (2) | 0.09209 (14) | 0.0236 (4) | |
C13 | 0.9193 (3) | −0.2164 (2) | 0.16938 (14) | 0.0262 (4) | |
H13 | 0.8146 | −0.2464 | 0.1545 | 0.031* | |
C14 | 0.9434 (3) | −0.2110 (3) | 0.26848 (15) | 0.0310 (4) | |
H14 | 0.8561 | −0.2382 | 0.3194 | 0.037* | |
C15 | 1.0985 (3) | −0.1646 (3) | 0.29140 (15) | 0.0353 (5) | |
H15 | 1.1139 | −0.1585 | 0.3579 | 0.042* | |
C16 | 1.2297 (3) | −0.1275 (3) | 0.21547 (17) | 0.0356 (5) | |
H16 | 1.3347 | −0.0984 | 0.2306 | 0.043* | |
C17 | 1.2047 (3) | −0.1337 (3) | 0.11608 (16) | 0.0304 (4) | |
H17 | 1.2931 | −0.1079 | 0.0652 | 0.036* | |
N21 | 0.4899 (2) | 0.8958 (2) | 0.67886 (10) | 0.0215 (3) | |
C22 | 0.6232 (2) | 0.8630 (2) | 0.73778 (13) | 0.0228 (3) | |
O22 | 0.7237 (2) | 0.96498 (19) | 0.74289 (10) | 0.0323 (3) | |
C23 | 0.6511 (2) | 0.6939 (2) | 0.80252 (13) | 0.0224 (3) | |
H23 | 0.6387 | 0.7431 | 0.8715 | 0.027* | |
N24 | 0.50558 (19) | 0.6001 (2) | 0.80523 (11) | 0.0218 (3) | |
C24 | 0.5026 (3) | 0.4597 (3) | 0.88025 (14) | 0.0293 (4) | |
H24A | 0.3717 | 0.4618 | 0.9024 | 0.044* | |
H24B | 0.5519 | 0.4903 | 0.9367 | 0.044* | |
H24C | 0.5822 | 0.3349 | 0.8510 | 0.044* | |
C25 | 0.4023 (2) | 0.6079 (2) | 0.73241 (13) | 0.0229 (3) | |
O25 | 0.30625 (19) | 0.50239 (19) | 0.72680 (11) | 0.0347 (3) | |
C26 | 0.3921 (2) | 0.7623 (2) | 0.65851 (13) | 0.0223 (3) | |
H26 | 0.2544 | 0.8377 | 0.6646 | 0.027* | |
C27 | 0.4637 (3) | 0.6798 (3) | 0.54885 (13) | 0.0260 (4) | |
H27A | 0.5994 | 0.6009 | 0.5394 | 0.031* | |
H27B | 0.3902 | 0.6001 | 0.5341 | 0.031* | |
C28 | 0.4401 (3) | 0.8393 (3) | 0.47708 (14) | 0.0330 (4) | |
H28A | 0.3029 | 0.9052 | 0.4791 | 0.040* | |
H28B | 0.4985 | 0.7848 | 0.4090 | 0.040* | |
C29 | 0.5342 (3) | 0.9824 (3) | 0.50395 (14) | 0.0324 (4) | |
H29A | 0.6741 | 0.9214 | 0.4926 | 0.039* | |
H29B | 0.5053 | 1.0882 | 0.4609 | 0.039* | |
C210 | 0.4591 (3) | 1.0569 (2) | 0.61376 (14) | 0.0278 (4) | |
H21A | 0.5269 | 1.1401 | 0.6313 | 0.033* | |
H21B | 0.3217 | 1.1302 | 0.6237 | 0.033* | |
C211 | 0.8604 (2) | 0.5522 (3) | 0.77144 (14) | 0.0257 (4) | |
H21C | 0.9509 | 0.6181 | 0.7785 | 0.031* | |
H21D | 0.8794 | 0.4504 | 0.8172 | 0.031* | |
C212 | 0.9070 (2) | 0.4656 (2) | 0.66521 (13) | 0.0233 (4) | |
C213 | 0.8709 (3) | 0.2984 (3) | 0.64377 (15) | 0.0283 (4) | |
H213 | 0.8182 | 0.2386 | 0.6958 | 0.034* | |
C214 | 0.9128 (3) | 0.2204 (3) | 0.54578 (17) | 0.0344 (4) | |
H214 | 0.8883 | 0.1087 | 0.5327 | 0.041* | |
C215 | 0.9904 (3) | 0.3074 (3) | 0.46757 (15) | 0.0336 (4) | |
H215 | 1.0168 | 0.2557 | 0.4018 | 0.040* | |
C216 | 1.0287 (3) | 0.4728 (3) | 0.48791 (14) | 0.0310 (4) | |
H216 | 1.0831 | 0.5312 | 0.4358 | 0.037* | |
C217 | 0.9859 (2) | 0.5512 (3) | 0.58620 (14) | 0.0264 (4) | |
H217 | 1.0106 | 0.6629 | 0.5991 | 0.032* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0209 (7) | 0.0233 (7) | 0.0218 (7) | −0.0066 (6) | −0.0011 (5) | −0.0020 (6) |
C2 | 0.0234 (8) | 0.0240 (8) | 0.0222 (9) | −0.0089 (7) | −0.0058 (7) | 0.0011 (7) |
O2 | 0.0298 (7) | 0.0336 (7) | 0.0358 (7) | −0.0159 (6) | −0.0029 (6) | −0.0062 (6) |
C3 | 0.0256 (8) | 0.0196 (8) | 0.0206 (8) | −0.0082 (7) | −0.0030 (6) | −0.0027 (6) |
N4 | 0.0238 (7) | 0.0197 (7) | 0.0235 (7) | −0.0081 (6) | −0.0005 (5) | 0.0000 (6) |
C4 | 0.0262 (9) | 0.0278 (9) | 0.0297 (9) | −0.0075 (7) | 0.0028 (7) | 0.0010 (7) |
C5 | 0.0264 (8) | 0.0179 (8) | 0.0256 (9) | −0.0054 (7) | −0.0056 (7) | 0.0019 (6) |
O5 | 0.0371 (7) | 0.0276 (7) | 0.0439 (8) | −0.0172 (6) | −0.0049 (6) | −0.0016 (6) |
C6 | 0.0276 (9) | 0.0153 (7) | 0.0256 (9) | −0.0057 (7) | −0.0063 (7) | 0.0002 (6) |
C7 | 0.0333 (9) | 0.0220 (8) | 0.0244 (9) | −0.0080 (7) | −0.0070 (7) | −0.0027 (7) |
C8 | 0.0388 (10) | 0.0343 (10) | 0.0228 (9) | −0.0059 (8) | −0.0017 (8) | −0.0065 (8) |
C9 | 0.0310 (10) | 0.0402 (11) | 0.0270 (10) | −0.0085 (9) | 0.0055 (8) | −0.0041 (8) |
C10 | 0.0200 (8) | 0.0317 (10) | 0.0312 (10) | −0.0041 (7) | 0.0001 (7) | −0.0045 (8) |
C11 | 0.0286 (9) | 0.0184 (8) | 0.0262 (9) | −0.0061 (7) | −0.0010 (7) | −0.0034 (7) |
C12 | 0.0251 (8) | 0.0142 (7) | 0.0289 (9) | −0.0031 (6) | −0.0053 (7) | 0.0008 (6) |
C13 | 0.0283 (9) | 0.0184 (8) | 0.0325 (9) | −0.0081 (7) | −0.0069 (7) | −0.0003 (7) |
C14 | 0.0373 (10) | 0.0260 (9) | 0.0283 (9) | −0.0099 (8) | −0.0038 (8) | 0.0032 (7) |
C15 | 0.0490 (12) | 0.0286 (10) | 0.0324 (11) | −0.0124 (9) | −0.0193 (9) | 0.0053 (8) |
C16 | 0.0375 (10) | 0.0297 (10) | 0.0489 (12) | −0.0158 (8) | −0.0232 (9) | 0.0088 (9) |
C17 | 0.0272 (9) | 0.0233 (9) | 0.0411 (11) | −0.0074 (7) | −0.0098 (8) | 0.0089 (8) |
N21 | 0.0246 (7) | 0.0194 (7) | 0.0209 (7) | −0.0077 (6) | −0.0047 (6) | 0.0005 (5) |
C22 | 0.0247 (8) | 0.0215 (8) | 0.0225 (8) | −0.0084 (7) | −0.0035 (7) | −0.0026 (6) |
O22 | 0.0394 (7) | 0.0313 (7) | 0.0358 (7) | −0.0208 (6) | −0.0147 (6) | 0.0060 (6) |
C23 | 0.0226 (8) | 0.0254 (8) | 0.0213 (8) | −0.0102 (7) | −0.0052 (6) | 0.0008 (7) |
N24 | 0.0206 (7) | 0.0211 (7) | 0.0235 (7) | −0.0073 (6) | −0.0030 (5) | 0.0022 (5) |
C24 | 0.0275 (9) | 0.0273 (9) | 0.0313 (10) | −0.0080 (7) | −0.0035 (7) | 0.0068 (7) |
C25 | 0.0153 (7) | 0.0233 (8) | 0.0290 (9) | −0.0059 (6) | −0.0022 (6) | −0.0013 (7) |
O25 | 0.0307 (7) | 0.0344 (7) | 0.0452 (8) | −0.0177 (6) | −0.0103 (6) | 0.0031 (6) |
C26 | 0.0179 (7) | 0.0229 (8) | 0.0253 (8) | −0.0055 (6) | −0.0046 (6) | −0.0031 (7) |
C27 | 0.0235 (8) | 0.0288 (9) | 0.0257 (9) | −0.0085 (7) | −0.0055 (7) | −0.0053 (7) |
C28 | 0.0382 (11) | 0.0363 (10) | 0.0229 (9) | −0.0077 (9) | −0.0108 (8) | −0.0007 (8) |
C29 | 0.0421 (11) | 0.0321 (10) | 0.0230 (9) | −0.0119 (9) | −0.0070 (8) | 0.0057 (8) |
C210 | 0.0342 (10) | 0.0202 (8) | 0.0280 (9) | −0.0059 (7) | −0.0094 (7) | 0.0041 (7) |
C211 | 0.0208 (8) | 0.0300 (9) | 0.0265 (9) | −0.0071 (7) | −0.0072 (7) | 0.0037 (7) |
C212 | 0.0165 (7) | 0.0236 (8) | 0.0283 (9) | −0.0044 (7) | −0.0054 (7) | 0.0004 (7) |
C213 | 0.0233 (9) | 0.0240 (8) | 0.0355 (10) | −0.0082 (7) | 0.0004 (7) | 0.0006 (7) |
C214 | 0.0282 (9) | 0.0274 (9) | 0.0462 (12) | −0.0100 (8) | −0.0024 (8) | −0.0090 (8) |
C215 | 0.0279 (9) | 0.0347 (10) | 0.0319 (10) | −0.0040 (8) | −0.0025 (8) | −0.0110 (8) |
C216 | 0.0266 (9) | 0.0344 (10) | 0.0280 (10) | −0.0071 (8) | −0.0012 (7) | 0.0033 (8) |
C217 | 0.0212 (8) | 0.0246 (8) | 0.0335 (10) | −0.0074 (7) | −0.0056 (7) | 0.0015 (7) |
N1—C2 | 1.342 (2) | N21—C22 | 1.342 (2) |
N1—C6 | 1.459 (2) | N21—C26 | 1.460 (2) |
N1—C10 | 1.473 (2) | N21—C210 | 1.471 (2) |
C2—O2 | 1.234 (2) | C22—O22 | 1.236 (2) |
C2—C3 | 1.512 (2) | C22—C23 | 1.514 (2) |
C3—N4 | 1.466 (2) | C23—N24 | 1.462 (2) |
C3—C11 | 1.544 (2) | C23—C211 | 1.546 (2) |
C3—H3 | 0.9800 | C23—H23 | 0.9800 |
N4—C5 | 1.345 (2) | N24—C25 | 1.343 (2) |
N4—C4 | 1.469 (2) | N24—C24 | 1.462 (2) |
C4—H4A | 0.9600 | C24—H24A | 0.9600 |
C4—H4B | 0.9600 | C24—H24B | 0.9600 |
C4—H4C | 0.9600 | C24—H24C | 0.9600 |
C5—O5 | 1.228 (2) | C25—O25 | 1.232 (2) |
C5—C6 | 1.520 (2) | C25—C26 | 1.518 (3) |
C6—C7 | 1.535 (2) | C26—C27 | 1.537 (2) |
C6—H6 | 0.9800 | C26—H26 | 0.9800 |
C7—C8 | 1.526 (3) | C27—C28 | 1.521 (3) |
C7—H7A | 0.9700 | C27—H27A | 0.9700 |
C7—H7B | 0.9700 | C27—H27B | 0.9700 |
C8—C9 | 1.517 (3) | C28—C29 | 1.527 (3) |
C8—H8A | 0.9700 | C28—H28A | 0.9700 |
C8—H8B | 0.9700 | C28—H28B | 0.9700 |
C9—C10 | 1.520 (3) | C29—C210 | 1.525 (3) |
C9—H9A | 0.9700 | C29—H29A | 0.9700 |
C9—H9B | 0.9700 | C29—H29B | 0.9700 |
C10—H10A | 0.9700 | C210—H21A | 0.9700 |
C10—H10B | 0.9700 | C210—H21B | 0.9700 |
C11—C12 | 1.504 (3) | C211—C212 | 1.508 (2) |
C11—H11A | 0.9700 | C211—H21C | 0.9700 |
C11—H11B | 0.9700 | C211—H21D | 0.9700 |
C12—C13 | 1.388 (3) | C212—C217 | 1.385 (3) |
C12—C17 | 1.393 (2) | C212—C213 | 1.396 (2) |
C13—C14 | 1.387 (3) | C213—C214 | 1.386 (3) |
C13—H13 | 0.9300 | C213—H213 | 0.9300 |
C14—C15 | 1.390 (3) | C214—C215 | 1.380 (3) |
C14—H14 | 0.9300 | C214—H214 | 0.9300 |
C15—C16 | 1.379 (3) | C215—C216 | 1.388 (3) |
C15—H15 | 0.9300 | C215—H215 | 0.9300 |
C16—C17 | 1.393 (3) | C216—C217 | 1.391 (3) |
C16—H16 | 0.9300 | C216—H216 | 0.9300 |
C17—H17 | 0.9300 | C217—H217 | 0.9300 |
C2—N1—C6 | 124.78 (14) | C22—N21—C26 | 124.54 (15) |
C2—N1—C10 | 120.78 (14) | C22—N21—C210 | 120.64 (14) |
C6—N1—C10 | 113.58 (13) | C26—N21—C210 | 113.85 (13) |
O2—C2—N1 | 123.22 (15) | O22—C22—N21 | 123.37 (16) |
O2—C2—C3 | 117.96 (14) | O22—C22—C23 | 118.02 (15) |
N1—C2—C3 | 118.82 (14) | N21—C22—C23 | 118.60 (14) |
N4—C3—C2 | 114.35 (13) | N24—C23—C22 | 114.55 (13) |
N4—C3—C11 | 111.80 (14) | N24—C23—C211 | 112.15 (14) |
C2—C3—C11 | 109.80 (14) | C22—C23—C211 | 109.77 (14) |
N4—C3—H3 | 106.8 | N24—C23—H23 | 106.6 |
C2—C3—H3 | 106.8 | C22—C23—H23 | 106.6 |
C11—C3—H3 | 106.8 | C211—C23—H23 | 106.6 |
C5—N4—C3 | 124.19 (14) | C25—N24—C24 | 117.94 (14) |
C5—N4—C4 | 117.67 (14) | C25—N24—C23 | 123.74 (14) |
C3—N4—C4 | 116.88 (14) | C24—N24—C23 | 117.07 (14) |
N4—C4—H4A | 109.5 | N24—C24—H24A | 109.5 |
N4—C4—H4B | 109.5 | N24—C24—H24B | 109.5 |
H4A—C4—H4B | 109.5 | H24A—C24—H24B | 109.5 |
N4—C4—H4C | 109.5 | N24—C24—H24C | 109.5 |
H4A—C4—H4C | 109.5 | H24A—C24—H24C | 109.5 |
H4B—C4—H4C | 109.5 | H24B—C24—H24C | 109.5 |
O5—C5—N4 | 122.71 (16) | O25—C25—N24 | 122.71 (16) |
O5—C5—C6 | 118.97 (15) | O25—C25—C26 | 118.64 (15) |
N4—C5—C6 | 118.21 (15) | N24—C25—C26 | 118.50 (14) |
N1—C6—C5 | 114.98 (13) | N21—C26—C25 | 114.78 (14) |
N1—C6—C7 | 110.40 (14) | N21—C26—C27 | 109.97 (14) |
C5—C6—C7 | 111.53 (14) | C25—C26—C27 | 112.28 (14) |
N1—C6—H6 | 106.4 | N21—C26—H26 | 106.4 |
C5—C6—H6 | 106.4 | C25—C26—H26 | 106.4 |
C7—C6—H6 | 106.4 | C27—C26—H26 | 106.4 |
C8—C7—C6 | 110.53 (15) | C28—C27—C26 | 110.57 (14) |
C8—C7—H7A | 109.5 | C28—C27—H27A | 109.5 |
C6—C7—H7A | 109.5 | C26—C27—H27A | 109.5 |
C8—C7—H7B | 109.5 | C28—C27—H27B | 109.5 |
C6—C7—H7B | 109.5 | C26—C27—H27B | 109.5 |
H7A—C7—H7B | 108.1 | H27A—C27—H27B | 108.1 |
C9—C8—C7 | 111.44 (15) | C27—C28—C29 | 111.93 (15) |
C9—C8—H8A | 109.3 | C27—C28—H28A | 109.2 |
C7—C8—H8A | 109.3 | C29—C28—H28A | 109.2 |
C9—C8—H8B | 109.3 | C27—C28—H28B | 109.2 |
C7—C8—H8B | 109.3 | C29—C28—H28B | 109.2 |
H8A—C8—H8B | 108.0 | H28A—C28—H28B | 107.9 |
C8—C9—C10 | 111.17 (16) | C210—C29—C28 | 110.50 (16) |
C8—C9—H9A | 109.4 | C210—C29—H29A | 109.5 |
C10—C9—H9A | 109.4 | C28—C29—H29A | 109.5 |
C8—C9—H9B | 109.4 | C210—C29—H29B | 109.5 |
C10—C9—H9B | 109.4 | C28—C29—H29B | 109.5 |
H9A—C9—H9B | 108.0 | H29A—C29—H29B | 108.1 |
N1—C10—C9 | 109.56 (14) | N21—C210—C29 | 109.72 (14) |
N1—C10—H10A | 109.8 | N21—C210—H21A | 109.7 |
C9—C10—H10A | 109.8 | C29—C210—H21A | 109.7 |
N1—C10—H10B | 109.8 | N21—C210—H21B | 109.7 |
C9—C10—H10B | 109.8 | C29—C210—H21B | 109.7 |
H10A—C10—H10B | 108.2 | H21A—C210—H21B | 108.2 |
C12—C11—C3 | 113.82 (13) | C212—C211—C23 | 113.88 (14) |
C12—C11—H11A | 108.8 | C212—C211—H21C | 108.8 |
C3—C11—H11A | 108.8 | C23—C211—H21C | 108.8 |
C12—C11—H11B | 108.8 | C212—C211—H21D | 108.8 |
C3—C11—H11B | 108.8 | C23—C211—H21D | 108.8 |
H11A—C11—H11B | 107.7 | H21C—C211—H21D | 107.7 |
C13—C12—C17 | 118.49 (17) | C217—C212—C213 | 118.33 (16) |
C13—C12—C11 | 120.18 (16) | C217—C212—C211 | 120.61 (15) |
C17—C12—C11 | 121.32 (16) | C213—C212—C211 | 121.06 (16) |
C14—C13—C12 | 121.14 (17) | C214—C213—C212 | 120.71 (17) |
C14—C13—H13 | 119.4 | C214—C213—H213 | 119.6 |
C12—C13—H13 | 119.4 | C212—C213—H213 | 119.6 |
C13—C14—C15 | 119.73 (18) | C215—C214—C213 | 120.48 (18) |
C13—C14—H14 | 120.1 | C215—C214—H214 | 119.8 |
C15—C14—H14 | 120.1 | C213—C214—H214 | 119.8 |
C16—C15—C14 | 119.96 (17) | C214—C215—C216 | 119.42 (17) |
C16—C15—H15 | 120.0 | C214—C215—H215 | 120.3 |
C14—C15—H15 | 120.0 | C216—C215—H215 | 120.3 |
C15—C16—C17 | 119.96 (17) | C215—C216—C217 | 120.01 (18) |
C15—C16—H16 | 120.0 | C215—C216—H216 | 120.0 |
C17—C16—H16 | 120.0 | C217—C216—H216 | 120.0 |
C12—C17—C16 | 120.72 (18) | C212—C217—C216 | 121.04 (17) |
C12—C17—H17 | 119.6 | C212—C217—H217 | 119.5 |
C16—C17—H17 | 119.6 | C216—C217—H217 | 119.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O22i | 0.98 | 2.44 | 3.386 (2) | 161 |
C11—H11A···O5ii | 0.97 | 2.48 | 3.169 (2) | 128 |
C17—H17···O2iii | 0.93 | 2.45 | 3.279 (2) | 149 |
C211—H21C···O25iii | 0.97 | 2.46 | 3.154 (2) | 129 |
C23—H23···O2iv | 0.98 | 2.47 | 3.405 (2) | 160 |
C213—H213···O22ii | 0.93 | 2.41 | 3.229 (2) | 146 |
Symmetry codes: (i) x, y−1, z−1; (ii) x, y−1, z; (iii) x+1, y, z; (iv) x, y+1, z+1. |
C16H20N2O2 | F(000) = 584 |
Mr = 272.34 | Dx = 1.245 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1930 reflections |
a = 10.0530 (3) Å | θ = 1–27.5° |
b = 10.8372 (2) Å | µ = 0.08 mm−1 |
c = 13.3352 (5) Å | T = 150 K |
V = 1452.82 (7) Å3 | Prism, colourless |
Z = 4 | 0.35 × 0.35 × 0.2 mm |
Nonius KappaCCD area detector diffractometer | 3001 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 27.5°, θmin = 2.4° |
Detector resolution: 9.091 pixels mm-1 | h = −13→13 |
φ and ω scans to fill the Ewald sphere | k = −14→14 |
19589 measured reflections | l = −17→17 |
3329 independent reflections |
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)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.084 | w = 1/[σ2(Fo2) + (0.0412P)2 + 0.1777P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3329 reflections | Δρmax = 0.11 e Å−3 |
182 parameters | Δρmin = −0.15 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.0 (10) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.76966 (11) | 0.78748 (9) | 0.10030 (8) | 0.0309 (2) | |
C2 | 0.71461 (13) | 0.88638 (11) | 0.14480 (10) | 0.0318 (3) | |
C3 | 0.63673 (12) | 0.86737 (11) | 0.24015 (10) | 0.0307 (3) | |
H3 | 0.5556 | 0.9170 | 0.2348 | 0.037* | |
N4 | 0.59584 (9) | 0.74034 (9) | 0.25791 (8) | 0.0272 (2) | |
C5 | 0.65930 (11) | 0.64213 (11) | 0.22008 (9) | 0.0254 (2) | |
C6 | 0.76476 (12) | 0.66229 (10) | 0.14093 (9) | 0.0269 (2) | |
H6 | 0.8514 | 0.6445 | 0.1714 | 0.032* | |
C7 | 0.74331 (15) | 0.57026 (12) | 0.05532 (10) | 0.0388 (3) | |
H7A | 0.7484 | 0.4869 | 0.0815 | 0.047* | |
H7B | 0.6551 | 0.5819 | 0.0273 | 0.047* | |
C8 | 0.8463 (2) | 0.58622 (16) | −0.02691 (13) | 0.0584 (5) | |
H8A | 0.9339 | 0.5667 | −0.0009 | 0.070* | |
H8B | 0.8272 | 0.5299 | −0.0816 | 0.070* | |
C9 | 0.8446 (2) | 0.71804 (16) | −0.06530 (12) | 0.0554 (4) | |
H9A | 0.9137 | 0.7287 | −0.1154 | 0.066* | |
H9B | 0.7595 | 0.7352 | −0.0967 | 0.066* | |
C10 | 0.86717 (16) | 0.80670 (15) | 0.01999 (12) | 0.0469 (4) | |
H10A | 0.9562 | 0.7952 | 0.0465 | 0.056* | |
H10B | 0.8603 | 0.8907 | −0.0046 | 0.056* | |
C11 | 0.71812 (14) | 0.91938 (12) | 0.32945 (11) | 0.0356 (3) | |
H11A | 0.7317 | 1.0072 | 0.3197 | 0.043* | |
H11B | 0.6678 | 0.9084 | 0.3909 | 0.043* | |
C12 | 0.85125 (13) | 0.85690 (11) | 0.34014 (10) | 0.0316 (3) | |
C13 | 0.96202 (14) | 0.90234 (12) | 0.29004 (12) | 0.0379 (3) | |
H13 | 0.9553 | 0.9753 | 0.2537 | 0.046* | |
C14 | 1.08261 (14) | 0.84019 (14) | 0.29353 (13) | 0.0438 (4) | |
H14 | 1.1561 | 0.8717 | 0.2598 | 0.053* | |
C15 | 1.09351 (15) | 0.73154 (14) | 0.34716 (13) | 0.0460 (4) | |
H15 | 1.1740 | 0.6893 | 0.3491 | 0.055* | |
C16 | 0.98416 (16) | 0.68598 (13) | 0.39784 (13) | 0.0442 (4) | |
H16 | 0.9913 | 0.6130 | 0.4341 | 0.053* | |
C17 | 0.86397 (14) | 0.74835 (12) | 0.39499 (11) | 0.0365 (3) | |
H17 | 0.7912 | 0.7174 | 0.4300 | 0.044* | |
C18 | 0.49168 (14) | 0.72095 (14) | 0.33300 (11) | 0.0393 (3) | |
H18A | 0.4422 | 0.6479 | 0.3166 | 0.059* | |
H18B | 0.4329 | 0.7908 | 0.3336 | 0.059* | |
H18C | 0.5316 | 0.7115 | 0.3979 | 0.059* | |
O2 | 0.72732 (11) | 0.99202 (9) | 0.11236 (9) | 0.0460 (3) | |
O5 | 0.63248 (9) | 0.53580 (8) | 0.24505 (7) | 0.0360 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0321 (5) | 0.0303 (5) | 0.0305 (5) | −0.0033 (4) | 0.0036 (5) | 0.0031 (4) |
C2 | 0.0271 (6) | 0.0284 (6) | 0.0400 (7) | −0.0032 (5) | −0.0070 (5) | 0.0034 (5) |
C3 | 0.0257 (6) | 0.0241 (6) | 0.0424 (7) | 0.0033 (5) | −0.0017 (5) | −0.0031 (5) |
N4 | 0.0233 (4) | 0.0267 (5) | 0.0315 (5) | −0.0007 (4) | 0.0033 (4) | −0.0012 (4) |
C5 | 0.0226 (5) | 0.0260 (6) | 0.0276 (6) | 0.0009 (5) | −0.0026 (5) | 0.0006 (5) |
C6 | 0.0235 (5) | 0.0282 (6) | 0.0288 (6) | 0.0016 (5) | 0.0009 (5) | 0.0013 (5) |
C7 | 0.0503 (9) | 0.0337 (7) | 0.0324 (7) | 0.0060 (6) | 0.0028 (6) | −0.0066 (5) |
C8 | 0.0748 (12) | 0.0610 (10) | 0.0395 (9) | 0.0158 (9) | 0.0208 (9) | −0.0068 (8) |
C9 | 0.0637 (10) | 0.0679 (11) | 0.0346 (8) | 0.0045 (9) | 0.0180 (8) | 0.0050 (7) |
C10 | 0.0422 (8) | 0.0568 (9) | 0.0418 (8) | −0.0049 (7) | 0.0136 (7) | 0.0108 (7) |
C11 | 0.0342 (7) | 0.0294 (6) | 0.0431 (8) | 0.0024 (5) | −0.0012 (6) | −0.0106 (6) |
C12 | 0.0326 (6) | 0.0285 (6) | 0.0338 (7) | 0.0003 (5) | −0.0059 (6) | −0.0094 (5) |
C13 | 0.0348 (7) | 0.0316 (7) | 0.0474 (8) | −0.0046 (5) | −0.0057 (6) | −0.0022 (6) |
C14 | 0.0302 (7) | 0.0446 (8) | 0.0564 (9) | −0.0030 (6) | −0.0012 (7) | −0.0104 (7) |
C15 | 0.0347 (7) | 0.0410 (8) | 0.0623 (10) | 0.0069 (6) | −0.0142 (7) | −0.0143 (7) |
C16 | 0.0502 (9) | 0.0345 (7) | 0.0479 (9) | 0.0035 (6) | −0.0172 (7) | −0.0003 (7) |
C17 | 0.0394 (7) | 0.0383 (7) | 0.0320 (7) | −0.0031 (6) | −0.0047 (6) | −0.0025 (6) |
C18 | 0.0315 (7) | 0.0449 (8) | 0.0414 (8) | −0.0004 (6) | 0.0107 (6) | −0.0037 (6) |
O2 | 0.0470 (6) | 0.0285 (5) | 0.0624 (7) | −0.0050 (4) | −0.0031 (6) | 0.0122 (4) |
O5 | 0.0362 (5) | 0.0273 (4) | 0.0444 (5) | −0.0022 (4) | 0.0080 (4) | 0.0046 (4) |
N1—C2 | 1.3442 (17) | C9—H9A | 0.9700 |
N1—C6 | 1.4618 (15) | C9—H9B | 0.9700 |
N1—C10 | 1.4667 (17) | C10—H10A | 0.9700 |
C2—O2 | 1.2305 (15) | C10—H10B | 0.9700 |
C2—C3 | 1.5074 (19) | C11—C12 | 1.5067 (18) |
C3—N4 | 1.4561 (15) | C11—H11A | 0.9700 |
C3—C11 | 1.5509 (19) | C11—H11B | 0.9700 |
C3—H3 | 0.9800 | C12—C13 | 1.3887 (19) |
N4—C5 | 1.3396 (15) | C12—C17 | 1.3912 (19) |
N4—C18 | 1.4640 (16) | C13—C14 | 1.388 (2) |
C5—O5 | 1.2294 (14) | C13—H13 | 0.9300 |
C5—C6 | 1.5118 (17) | C14—C15 | 1.382 (2) |
C6—C7 | 1.5312 (17) | C14—H14 | 0.9300 |
C6—H6 | 0.9800 | C15—C16 | 1.382 (2) |
C7—C8 | 1.518 (2) | C15—H15 | 0.9300 |
C7—H7A | 0.9700 | C16—C17 | 1.385 (2) |
C7—H7B | 0.9700 | C16—H16 | 0.9300 |
C8—C9 | 1.518 (2) | C17—H17 | 0.9300 |
C8—H8A | 0.9700 | C18—H18A | 0.9600 |
C8—H8B | 0.9700 | C18—H18B | 0.9600 |
C9—C10 | 1.506 (2) | C18—H18C | 0.9600 |
C2—N1—C6 | 124.22 (11) | C10—C9—H9B | 109.6 |
C2—N1—C10 | 118.97 (11) | C8—C9—H9B | 109.6 |
C6—N1—C10 | 115.15 (11) | H9A—C9—H9B | 108.1 |
O2—C2—N1 | 122.94 (13) | N1—C10—C9 | 111.11 (13) |
O2—C2—C3 | 118.53 (12) | N1—C10—H10A | 109.4 |
N1—C2—C3 | 118.51 (11) | C9—C10—H10A | 109.4 |
N4—C3—C2 | 114.39 (10) | N1—C10—H10B | 109.4 |
N4—C3—C11 | 111.58 (11) | C9—C10—H10B | 109.4 |
C2—C3—C11 | 108.91 (10) | H10A—C10—H10B | 108.0 |
N4—C3—H3 | 107.2 | C12—C11—C3 | 112.21 (10) |
C2—C3—H3 | 107.2 | C12—C11—H11A | 109.2 |
C11—C3—H3 | 107.2 | C3—C11—H11A | 109.2 |
C5—N4—C3 | 123.75 (10) | C12—C11—H11B | 109.2 |
C5—N4—C18 | 118.96 (10) | C3—C11—H11B | 109.2 |
C3—N4—C18 | 116.67 (10) | H11A—C11—H11B | 107.9 |
O5—C5—N4 | 122.57 (11) | C13—C12—C17 | 118.62 (13) |
O5—C5—C6 | 118.58 (10) | C13—C12—C11 | 120.49 (12) |
N4—C5—C6 | 118.82 (10) | C17—C12—C11 | 120.76 (12) |
N1—C6—C5 | 114.62 (10) | C14—C13—C12 | 120.82 (13) |
N1—C6—C7 | 109.45 (10) | C14—C13—H13 | 119.6 |
C5—C6—C7 | 109.13 (10) | C12—C13—H13 | 119.6 |
N1—C6—H6 | 107.8 | C15—C14—C13 | 120.01 (14) |
C5—C6—H6 | 107.8 | C15—C14—H14 | 120.0 |
C7—C6—H6 | 107.8 | C13—C14—H14 | 120.0 |
C8—C7—C6 | 111.61 (12) | C16—C15—C14 | 119.64 (14) |
C8—C7—H7A | 109.3 | C16—C15—H15 | 120.2 |
C6—C7—H7A | 109.3 | C14—C15—H15 | 120.2 |
C8—C7—H7B | 109.3 | C15—C16—C17 | 120.41 (14) |
C6—C7—H7B | 109.3 | C15—C16—H16 | 119.8 |
H7A—C7—H7B | 108.0 | C17—C16—H16 | 119.8 |
C9—C8—C7 | 110.07 (13) | C16—C17—C12 | 120.48 (14) |
C9—C8—H8A | 109.6 | C16—C17—H17 | 119.8 |
C7—C8—H8A | 109.6 | C12—C17—H17 | 119.8 |
C9—C8—H8B | 109.6 | N4—C18—H18A | 109.5 |
C7—C8—H8B | 109.6 | N4—C18—H18B | 109.5 |
H8A—C8—H8B | 108.2 | H18A—C18—H18B | 109.5 |
C10—C9—C8 | 110.13 (14) | N4—C18—H18C | 109.5 |
C10—C9—H9A | 109.6 | H18A—C18—H18C | 109.5 |
C8—C9—H9A | 109.6 | H18B—C18—H18C | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O5i | 0.98 | 2.30 | 3.2703 (14) | 169 |
C8—H8B···O5ii | 0.97 | 2.45 | 3.3228 (19) | 149 |
C15—H15···O2iii | 0.93 | 2.41 | 3.2053 (17) | 143 |
C18—H18A···O2iv | 0.96 | 2.58 | 3.3961 (17) | 143 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+3/2, −y+1, z−1/2; (iii) −x+2, y−1/2, −z+1/2; (iv) −x+1, y−1/2, −z+1/2. |
C14H16N2O2 | F(000) = 260 |
Mr = 244.29 | Dx = 1.345 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1446 reflections |
a = 5.6190 (2) Å | θ = 1–27.5° |
b = 10.0392 (3) Å | µ = 0.09 mm−1 |
c = 10.7068 (2) Å | T = 150 K |
β = 92.4862 (15)° | Prism, colourless |
V = 603.40 (3) Å3 | 0.4 × 0.3 × 0.25 mm |
Z = 2 |
Nonius KappaCCD area detector diffractometer | 2686 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.023 |
Graphite monochromator | θmax = 27.5°, θmin = 2.8° |
Detector resolution: 9.091 pixels mm-1 | h = −7→7 |
φ and ω scans to fill the Ewald sphere | k = −12→12 |
9184 measured reflections | l = −13→13 |
2749 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.027 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.070 | w = 1/[σ2(Fo2) + (0.0353P)2 + 0.0914P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max < 0.001 |
2749 reflections | Δρmax = 0.17 e Å−3 |
167 parameters | Δρmin = −0.14 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.2 (8) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.47099 (17) | 0.40434 (9) | 0.63512 (9) | 0.0209 (2) | |
C2 | 0.3039 (2) | 0.44530 (11) | 0.55118 (10) | 0.0199 (2) | |
C3 | 0.27201 (19) | 0.34395 (10) | 0.44400 (10) | 0.0191 (2) | |
H3 | 0.4207 | 0.3426 | 0.3995 | 0.023* | |
N4 | 0.24194 (17) | 0.21113 (9) | 0.49905 (9) | 0.02125 (19) | |
C5 | 0.39540 (19) | 0.16963 (11) | 0.59163 (10) | 0.0196 (2) | |
C6 | 0.58621 (18) | 0.27321 (10) | 0.62341 (10) | 0.0188 (2) | |
H6 | 0.6988 | 0.2767 | 0.5561 | 0.023* | |
C7 | 0.7233 (2) | 0.25498 (11) | 0.74796 (10) | 0.0242 (2) | |
H7A | 0.8687 | 0.2048 | 0.7377 | 0.029* | |
H7B | 0.6271 | 0.2095 | 0.8078 | 0.029* | |
C8 | 0.7782 (2) | 0.39800 (12) | 0.78970 (11) | 0.0262 (2) | |
H8A | 0.9171 | 0.4321 | 0.7495 | 0.031* | |
H8B | 0.8061 | 0.4027 | 0.8796 | 0.031* | |
C9 | 0.5543 (2) | 0.47610 (12) | 0.74836 (10) | 0.0240 (2) | |
H9A | 0.4363 | 0.4737 | 0.8118 | 0.029* | |
H9B | 0.5920 | 0.5681 | 0.7298 | 0.029* | |
C10 | 0.0722 (2) | 0.37830 (12) | 0.34892 (10) | 0.0231 (2) | |
H10A | −0.0782 | 0.3488 | 0.3805 | 0.028* | |
H10B | 0.0646 | 0.4743 | 0.3390 | 0.028* | |
C11 | 0.10575 (19) | 0.31493 (11) | 0.22284 (10) | 0.0211 (2) | |
C12 | −0.0579 (2) | 0.22343 (12) | 0.17195 (11) | 0.0257 (2) | |
H12 | −0.1924 | 0.2018 | 0.2153 | 0.031* | |
C13 | −0.0217 (2) | 0.16398 (13) | 0.05655 (12) | 0.0312 (3) | |
H13 | −0.1327 | 0.1035 | 0.0234 | 0.037* | |
C14 | 0.1776 (2) | 0.19435 (14) | −0.00865 (11) | 0.0326 (3) | |
H14 | 0.2024 | 0.1536 | −0.0850 | 0.039* | |
C15 | 0.3411 (2) | 0.28627 (15) | 0.04063 (11) | 0.0316 (3) | |
H15 | 0.4753 | 0.3075 | −0.0033 | 0.038* | |
C16 | 0.3055 (2) | 0.34645 (12) | 0.15475 (11) | 0.0258 (2) | |
H16 | 0.4153 | 0.4084 | 0.1865 | 0.031* | |
O2 | 0.19509 (14) | 0.55179 (8) | 0.55813 (7) | 0.02473 (18) | |
O5 | 0.38324 (14) | 0.06290 (8) | 0.64613 (8) | 0.02643 (19) | |
H4 | 0.112 (3) | 0.1635 (17) | 0.4789 (14) | 0.033 (4)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0259 (5) | 0.0164 (4) | 0.0203 (4) | 0.0022 (3) | −0.0001 (4) | −0.0014 (3) |
C2 | 0.0222 (5) | 0.0185 (5) | 0.0194 (5) | 0.0000 (4) | 0.0038 (4) | 0.0025 (4) |
C3 | 0.0210 (5) | 0.0168 (5) | 0.0196 (5) | 0.0022 (4) | 0.0018 (4) | 0.0012 (4) |
N4 | 0.0214 (4) | 0.0172 (4) | 0.0250 (5) | −0.0016 (4) | −0.0016 (3) | 0.0011 (3) |
C5 | 0.0197 (5) | 0.0178 (5) | 0.0215 (5) | 0.0011 (4) | 0.0028 (4) | −0.0009 (4) |
C6 | 0.0191 (5) | 0.0167 (5) | 0.0207 (5) | 0.0014 (4) | 0.0016 (4) | 0.0003 (4) |
C7 | 0.0255 (5) | 0.0216 (5) | 0.0250 (5) | 0.0018 (4) | −0.0047 (4) | −0.0002 (4) |
C8 | 0.0269 (5) | 0.0249 (6) | 0.0263 (6) | −0.0025 (5) | −0.0033 (5) | −0.0027 (5) |
C9 | 0.0292 (6) | 0.0198 (5) | 0.0228 (5) | −0.0002 (4) | −0.0005 (4) | −0.0035 (4) |
C10 | 0.0228 (5) | 0.0252 (6) | 0.0214 (5) | 0.0042 (4) | −0.0002 (4) | 0.0028 (4) |
C11 | 0.0211 (5) | 0.0210 (5) | 0.0211 (5) | 0.0038 (4) | −0.0012 (4) | 0.0047 (4) |
C12 | 0.0229 (5) | 0.0263 (6) | 0.0273 (6) | −0.0009 (4) | −0.0034 (4) | 0.0050 (4) |
C13 | 0.0349 (6) | 0.0277 (6) | 0.0300 (6) | −0.0004 (5) | −0.0111 (5) | −0.0006 (5) |
C14 | 0.0393 (6) | 0.0374 (7) | 0.0205 (5) | 0.0086 (6) | −0.0058 (5) | −0.0028 (5) |
C15 | 0.0288 (6) | 0.0438 (7) | 0.0223 (6) | 0.0027 (5) | 0.0031 (5) | 0.0033 (5) |
C16 | 0.0249 (5) | 0.0294 (6) | 0.0229 (5) | −0.0037 (4) | −0.0004 (4) | 0.0032 (5) |
O2 | 0.0286 (4) | 0.0187 (4) | 0.0270 (4) | 0.0059 (3) | 0.0021 (3) | 0.0000 (3) |
O5 | 0.0269 (4) | 0.0189 (4) | 0.0333 (4) | −0.0013 (3) | −0.0009 (3) | 0.0059 (3) |
N1—C2 | 1.3358 (14) | C8—H8A | 0.9700 |
N1—C9 | 1.4693 (14) | C8—H8B | 0.9700 |
N1—C6 | 1.4747 (13) | C9—H9A | 0.9700 |
C2—O2 | 1.2355 (13) | C9—H9B | 0.9700 |
C2—C3 | 1.5384 (15) | C10—C11 | 1.5115 (15) |
C3—N4 | 1.4706 (13) | C10—H10A | 0.9700 |
C3—C10 | 1.5219 (15) | C10—H10B | 0.9700 |
C3—H3 | 0.9800 | C11—C12 | 1.3937 (16) |
N4—C5 | 1.3511 (14) | C11—C16 | 1.4008 (15) |
N4—H4 | 0.890 (17) | C12—C13 | 1.3949 (18) |
C5—O5 | 1.2235 (14) | C12—H12 | 0.9300 |
C5—C6 | 1.5215 (15) | C13—C14 | 1.379 (2) |
C6—C7 | 1.5218 (14) | C13—H13 | 0.9300 |
C6—H6 | 0.9800 | C14—C15 | 1.390 (2) |
C7—C8 | 1.5312 (16) | C14—H14 | 0.9300 |
C7—H7A | 0.9700 | C15—C16 | 1.3854 (17) |
C7—H7B | 0.9700 | C15—H15 | 0.9300 |
C8—C9 | 1.5313 (16) | C16—H16 | 0.9300 |
C2—N1—C9 | 126.41 (10) | C7—C8—H8B | 110.9 |
C2—N1—C6 | 121.06 (9) | C9—C8—H8B | 110.9 |
C9—N1—C6 | 112.48 (9) | H8A—C8—H8B | 109.0 |
O2—C2—N1 | 124.13 (10) | N1—C9—C8 | 102.47 (9) |
O2—C2—C3 | 125.11 (10) | N1—C9—H9A | 111.3 |
N1—C2—C3 | 110.73 (9) | C8—C9—H9A | 111.3 |
N4—C3—C10 | 112.29 (9) | N1—C9—H9B | 111.3 |
N4—C3—C2 | 108.21 (8) | C8—C9—H9B | 111.3 |
C10—C3—C2 | 114.07 (9) | H9A—C9—H9B | 109.2 |
N4—C3—H3 | 107.3 | C11—C10—C3 | 112.66 (9) |
C10—C3—H3 | 107.3 | C11—C10—H10A | 109.1 |
C2—C3—H3 | 107.3 | C3—C10—H10A | 109.1 |
C5—N4—C3 | 119.52 (9) | C11—C10—H10B | 109.1 |
C5—N4—H4 | 120.1 (10) | C3—C10—H10B | 109.1 |
C3—N4—H4 | 119.8 (10) | H10A—C10—H10B | 107.8 |
O5—C5—N4 | 124.95 (10) | C12—C11—C16 | 118.37 (11) |
O5—C5—C6 | 123.04 (10) | C12—C11—C10 | 121.40 (10) |
N4—C5—C6 | 112.00 (9) | C16—C11—C10 | 120.22 (10) |
N1—C6—C5 | 108.75 (8) | C11—C12—C13 | 120.62 (11) |
N1—C6—C7 | 103.90 (8) | C11—C12—H12 | 119.7 |
C5—C6—C7 | 116.03 (9) | C13—C12—H12 | 119.7 |
N1—C6—H6 | 109.3 | C14—C13—C12 | 120.42 (12) |
C5—C6—H6 | 109.3 | C14—C13—H13 | 119.8 |
C7—C6—H6 | 109.3 | C12—C13—H13 | 119.8 |
C6—C7—C8 | 103.35 (9) | C13—C14—C15 | 119.51 (12) |
C6—C7—H7A | 111.1 | C13—C14—H14 | 120.2 |
C8—C7—H7A | 111.1 | C15—C14—H14 | 120.2 |
C6—C7—H7B | 111.1 | C16—C15—C14 | 120.37 (12) |
C8—C7—H7B | 111.1 | C16—C15—H15 | 119.8 |
H7A—C7—H7B | 109.1 | C14—C15—H15 | 119.8 |
C7—C8—C9 | 104.08 (9) | C15—C16—C11 | 120.68 (11) |
C7—C8—H8A | 110.9 | C15—C16—H16 | 119.7 |
C9—C8—H8A | 110.9 | C11—C16—H16 | 119.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O2i | 0.890 (17) | 2.083 (17) | 2.9721 (12) | 176.9 (14) |
Symmetry code: (i) −x, y−1/2, −z+1. |
C14H16N2O2 | F(000) = 260 |
Mr = 244.29 | Dx = 1.308 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 1507 reflections |
a = 7.8134 (3) Å | θ = 1–27.5° |
b = 6.5487 (2) Å | µ = 0.09 mm−1 |
c = 12.1725 (4) Å | T = 150 K |
β = 95.0641 (17)° | Bar, colourless |
V = 620.41 (4) Å3 | 0.4 × 0.2 × 0.12 mm |
Z = 2 |
Nonius KappaCCD area detector diffractometer | 2604 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.022 |
Graphite monochromator | θmax = 27.5°, θmin = 1.7° |
Detector resolution: 9.091 pixels mm-1 | h = −10→10 |
φ and ω scans to fill the Ewald sphere | k = −8→8 |
9305 measured reflections | l = −15→15 |
2831 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.081 | w = 1/[σ2(Fo2) + (0.0464P)2 + 0.0425P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2831 reflections | Δρmax = 0.29 e Å−3 |
167 parameters | Δρmin = −0.19 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.1 (9) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.97376 (13) | 0.81471 (15) | 0.69098 (9) | 0.0240 (2) | |
C2 | 0.90364 (15) | 0.62961 (18) | 0.69766 (10) | 0.0234 (3) | |
C3 | 0.71426 (16) | 0.60791 (18) | 0.66012 (10) | 0.0253 (3) | |
H3 | 0.7024 | 0.4848 | 0.6115 | 0.030* | |
N4 | 0.64478 (14) | 0.78083 (17) | 0.59458 (9) | 0.0276 (2) | |
H4 | 0.546 (2) | 0.758 (2) | 0.5541 (13) | 0.036 (4)* | |
C5 | 0.71573 (16) | 0.96488 (19) | 0.58671 (10) | 0.0269 (3) | |
C6 | 0.88671 (16) | 1.00140 (18) | 0.65147 (10) | 0.0241 (3) | |
H6 | 0.8679 | 1.0895 | 0.7164 | 0.029* | |
C7 | 1.02259 (16) | 1.10166 (19) | 0.58637 (10) | 0.0278 (3) | |
H7A | 1.0241 | 1.0400 | 0.5122 | 0.033* | |
H7B | 1.0028 | 1.2505 | 0.5786 | 0.033* | |
C8 | 1.18849 (17) | 1.0567 (2) | 0.65766 (12) | 0.0321 (3) | |
H8A | 1.2090 | 1.1605 | 0.7165 | 0.038* | |
H8B | 1.2878 | 1.0553 | 0.6125 | 0.038* | |
C9 | 1.16081 (17) | 0.8448 (2) | 0.70737 (13) | 0.0341 (3) | |
H9A | 1.2221 | 0.7382 | 0.6686 | 0.041* | |
H9B | 1.2013 | 0.8418 | 0.7867 | 0.041* | |
C11 | 0.61265 (16) | 0.5635 (2) | 0.76089 (11) | 0.0293 (3) | |
H11A | 0.4881 | 0.5731 | 0.7380 | 0.035* | |
H11B | 0.6371 | 0.4220 | 0.7863 | 0.035* | |
C12 | 0.65652 (16) | 0.7087 (2) | 0.85585 (11) | 0.0277 (3) | |
C13 | 0.77677 (17) | 0.6517 (2) | 0.94119 (11) | 0.0351 (3) | |
H13 | 0.8276 | 0.5200 | 0.9406 | 0.042* | |
C14 | 0.8234 (2) | 0.7843 (3) | 1.02710 (12) | 0.0440 (4) | |
H14 | 0.9065 | 0.7441 | 1.0847 | 0.053* | |
C15 | 0.7487 (2) | 0.9758 (3) | 1.02894 (13) | 0.0459 (4) | |
H15 | 0.7799 | 1.0665 | 1.0882 | 0.055* | |
C16 | 0.6291 (2) | 1.0352 (2) | 0.94499 (13) | 0.0399 (4) | |
H16 | 0.5780 | 1.1667 | 0.9464 | 0.048* | |
C17 | 0.58358 (18) | 0.9024 (2) | 0.85844 (12) | 0.0314 (3) | |
H17 | 0.5018 | 0.9441 | 0.8004 | 0.038* | |
O2 | 0.98647 (12) | 0.47946 (13) | 0.73194 (8) | 0.0295 (2) | |
O5 | 0.64784 (13) | 1.10497 (15) | 0.53046 (9) | 0.0401 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0217 (5) | 0.0224 (5) | 0.0273 (6) | 0.0021 (4) | −0.0017 (4) | 0.0036 (4) |
C2 | 0.0278 (6) | 0.0234 (6) | 0.0189 (6) | 0.0012 (5) | 0.0021 (5) | −0.0018 (5) |
C3 | 0.0281 (6) | 0.0216 (6) | 0.0253 (6) | −0.0012 (5) | −0.0031 (5) | −0.0034 (5) |
N4 | 0.0252 (5) | 0.0304 (6) | 0.0256 (6) | 0.0005 (4) | −0.0067 (5) | −0.0018 (5) |
C5 | 0.0277 (6) | 0.0269 (6) | 0.0252 (6) | 0.0059 (5) | −0.0027 (5) | −0.0024 (5) |
C6 | 0.0278 (6) | 0.0209 (6) | 0.0228 (6) | 0.0036 (5) | −0.0017 (5) | 0.0005 (5) |
C7 | 0.0365 (7) | 0.0217 (6) | 0.0253 (7) | −0.0014 (5) | 0.0026 (5) | 0.0017 (5) |
C8 | 0.0298 (6) | 0.0303 (7) | 0.0363 (8) | −0.0040 (5) | 0.0045 (5) | 0.0030 (5) |
C9 | 0.0233 (6) | 0.0344 (7) | 0.0435 (8) | −0.0009 (5) | −0.0021 (6) | 0.0101 (6) |
C11 | 0.0276 (6) | 0.0279 (6) | 0.0323 (7) | −0.0060 (5) | 0.0015 (5) | −0.0012 (5) |
C12 | 0.0229 (6) | 0.0349 (7) | 0.0261 (6) | −0.0046 (5) | 0.0069 (5) | 0.0002 (5) |
C13 | 0.0311 (7) | 0.0451 (8) | 0.0293 (7) | 0.0005 (6) | 0.0037 (6) | 0.0014 (6) |
C14 | 0.0364 (8) | 0.0668 (11) | 0.0280 (7) | −0.0022 (7) | −0.0021 (6) | −0.0033 (7) |
C15 | 0.0450 (8) | 0.0606 (10) | 0.0326 (7) | −0.0106 (8) | 0.0073 (7) | −0.0183 (8) |
C16 | 0.0384 (8) | 0.0416 (8) | 0.0416 (9) | −0.0040 (6) | 0.0137 (7) | −0.0119 (6) |
C17 | 0.0246 (6) | 0.0383 (7) | 0.0318 (7) | −0.0016 (5) | 0.0057 (5) | −0.0002 (6) |
O2 | 0.0329 (5) | 0.0232 (5) | 0.0320 (5) | 0.0046 (4) | −0.0006 (4) | 0.0022 (4) |
O5 | 0.0388 (5) | 0.0359 (5) | 0.0428 (6) | 0.0078 (4) | −0.0116 (5) | 0.0085 (5) |
N1—C2 | 1.3357 (16) | C8—H8A | 0.9900 |
N1—C6 | 1.4597 (15) | C8—H8B | 0.9900 |
N1—C9 | 1.4707 (17) | C9—H9A | 0.9900 |
C2—O2 | 1.2297 (15) | C9—H9B | 0.9900 |
C2—C3 | 1.5163 (17) | C11—C12 | 1.5128 (18) |
C3—N4 | 1.4619 (16) | C11—H11A | 0.9900 |
C3—C11 | 1.5465 (17) | C11—H11B | 0.9900 |
C3—H3 | 1.0000 | C12—C13 | 1.3889 (19) |
N4—C5 | 1.3336 (17) | C12—C17 | 1.392 (2) |
N4—H4 | 0.894 (17) | C13—C14 | 1.383 (2) |
C5—O5 | 1.2360 (16) | C13—H13 | 0.9500 |
C5—C6 | 1.5090 (17) | C14—C15 | 1.384 (3) |
C6—C7 | 1.5280 (17) | C14—H14 | 0.9500 |
C6—H6 | 1.0000 | C15—C16 | 1.378 (2) |
C7—C8 | 1.5236 (19) | C15—H15 | 0.9500 |
C7—H7A | 0.9900 | C16—C17 | 1.388 (2) |
C7—H7B | 0.9900 | C16—H16 | 0.9500 |
C8—C9 | 1.5367 (19) | C17—H17 | 0.9500 |
C2—N1—C6 | 126.76 (10) | C7—C8—H8B | 110.8 |
C2—N1—C9 | 121.42 (10) | C9—C8—H8B | 110.8 |
C6—N1—C9 | 111.17 (10) | H8A—C8—H8B | 108.8 |
O2—C2—N1 | 122.68 (11) | N1—C9—C8 | 103.90 (11) |
O2—C2—C3 | 119.85 (11) | N1—C9—H9A | 111.0 |
N1—C2—C3 | 117.47 (10) | C8—C9—H9A | 111.0 |
N4—C3—C2 | 113.41 (10) | N1—C9—H9B | 111.0 |
N4—C3—C11 | 112.75 (10) | C8—C9—H9B | 111.0 |
C2—C3—C11 | 109.53 (10) | H9A—C9—H9B | 109.0 |
N4—C3—H3 | 106.9 | C12—C11—C3 | 112.97 (10) |
C2—C3—H3 | 106.9 | C12—C11—H11A | 109.0 |
C11—C3—H3 | 106.9 | C3—C11—H11A | 109.0 |
C5—N4—C3 | 127.05 (11) | C12—C11—H11B | 109.0 |
C5—N4—H4 | 117.4 (10) | C3—C11—H11B | 109.0 |
C3—N4—H4 | 115.5 (10) | H11A—C11—H11B | 107.8 |
O5—C5—N4 | 123.35 (12) | C13—C12—C17 | 118.65 (13) |
O5—C5—C6 | 119.25 (12) | C13—C12—C11 | 119.67 (12) |
N4—C5—C6 | 117.40 (11) | C17—C12—C11 | 121.64 (13) |
N1—C6—C5 | 113.87 (10) | C14—C13—C12 | 120.80 (15) |
N1—C6—C7 | 101.88 (9) | C14—C13—H13 | 119.6 |
C5—C6—C7 | 114.89 (10) | C12—C13—H13 | 119.6 |
N1—C6—H6 | 108.6 | C13—C14—C15 | 119.87 (15) |
C5—C6—H6 | 108.6 | C13—C14—H14 | 120.1 |
C7—C6—H6 | 108.6 | C15—C14—H14 | 120.1 |
C8—C7—C6 | 102.52 (10) | C16—C15—C14 | 120.20 (15) |
C8—C7—H7A | 111.3 | C16—C15—H15 | 119.9 |
C6—C7—H7A | 111.3 | C14—C15—H15 | 119.9 |
C8—C7—H7B | 111.3 | C15—C16—C17 | 119.82 (15) |
C6—C7—H7B | 111.3 | C15—C16—H16 | 120.1 |
H7A—C7—H7B | 109.2 | C17—C16—H16 | 120.1 |
C7—C8—C9 | 104.87 (11) | C16—C17—C12 | 120.67 (14) |
C7—C8—H8A | 110.8 | C16—C17—H17 | 119.7 |
C9—C8—H8A | 110.8 | C12—C17—H17 | 119.7 |
C6—N1—C2—O2 | 179.90 (11) | N4—C5—C6—C7 | 132.51 (12) |
C9—N1—C2—O2 | 10.02 (19) | N1—C6—C7—C8 | −39.00 (12) |
C6—N1—C2—C3 | 0.34 (17) | C5—C6—C7—C8 | −162.60 (10) |
C9—N1—C2—C3 | −169.54 (12) | C6—C7—C8—C9 | 34.65 (13) |
O2—C2—C3—N4 | −164.18 (11) | C2—N1—C9—C8 | 162.72 (11) |
N1—C2—C3—N4 | 15.39 (15) | C6—N1—C9—C8 | −8.59 (15) |
O2—C2—C3—C11 | 68.90 (14) | C7—C8—C9—N1 | −16.79 (14) |
N1—C2—C3—C11 | −111.53 (12) | N4—C3—C11—C12 | −78.26 (14) |
C2—C3—N4—C5 | −16.20 (17) | C2—C3—C11—C12 | 49.04 (14) |
C11—C3—N4—C5 | 109.01 (14) | C3—C11—C12—C13 | −96.46 (14) |
C3—N4—C5—O5 | −179.00 (12) | C3—C11—C12—C17 | 81.32 (14) |
C3—N4—C5—C6 | 0.30 (18) | C17—C12—C13—C14 | −0.02 (18) |
C2—N1—C6—C5 | −16.31 (16) | C11—C12—C13—C14 | 177.83 (12) |
C9—N1—C6—C5 | 154.43 (11) | C12—C13—C14—C15 | 0.5 (2) |
C2—N1—C6—C7 | −140.60 (12) | C13—C14—C15—C16 | −0.5 (2) |
C9—N1—C6—C7 | 30.14 (13) | C14—C15—C16—C17 | 0.0 (2) |
O5—C5—C6—N1 | −165.12 (11) | C15—C16—C17—C12 | 0.5 (2) |
N4—C5—C6—N1 | 15.54 (15) | C13—C12—C17—C16 | −0.48 (18) |
O5—C5—C6—C7 | −48.16 (16) | C11—C12—C17—C16 | −178.28 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5i | 0.894 (17) | 2.017 (17) | 2.8733 (15) | 160.1 (15) |
C7—H7B···O2ii | 0.99 | 2.41 | 3.0707 (15) | 124 |
Symmetry codes: (i) −x+1, y−1/2, −z+1; (ii) x, y+1, z. |
C14H16N2O2 | F(000) = 260 |
Mr = 244.29 | Dx = 1.260 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2yb | Cell parameters from 25 reflections |
a = 8.0807 (7) Å | θ = 12–14° |
b = 6.6311 (6) Å | µ = 0.09 mm−1 |
c = 12.0895 (9) Å | T = 293 K |
β = 96.428 (7)° | Bar, colourless |
V = 643.73 (9) Å3 | 0.6 × 0.3 × 0.1 mm |
Z = 2 |
CAD4-MACHIII diffractometer | Rint = 0.028 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.7° |
Graphite monochromator | h = −9→9 |
θ–2θ scan | k = −7→7 |
2263 measured reflections | l = 0→14 |
2212 independent reflections | 3 standard reflections every 3600 min |
1942 reflections with I > 2σ(I) | intensity decay: 3% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0756P)2 + 0.0177P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
2212 reflections | Δρmax = 0.19 e Å−3 |
167 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.2 (15) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.46304 (19) | 0.2001 (2) | 0.69014 (13) | 0.0442 (4) | |
C2 | 0.3958 (2) | 0.0168 (3) | 0.69721 (14) | 0.0437 (4) | |
C3 | 0.2122 (2) | −0.0042 (3) | 0.65991 (16) | 0.0489 (4) | |
H3 | 0.1987 | −0.1250 | 0.6130 | 0.059* | |
N4 | 0.1441 (2) | 0.1635 (3) | 0.59236 (14) | 0.0541 (5) | |
H4 | 0.043 (3) | 0.136 (4) | 0.5508 (19) | 0.065 (7)* | |
C5 | 0.2102 (3) | 0.3463 (3) | 0.58604 (16) | 0.0518 (5) | |
C6 | 0.3757 (3) | 0.3834 (3) | 0.65098 (14) | 0.0450 (4) | |
H6 | 0.3593 | 0.4675 | 0.7155 | 0.054* | |
C7 | 0.5048 (3) | 0.4841 (3) | 0.58651 (17) | 0.0562 (5) | |
H7A | 0.5024 | 0.4275 | 0.5124 | 0.067* | |
H7B | 0.4860 | 0.6283 | 0.5806 | 0.067* | |
C8 | 0.6675 (3) | 0.4381 (4) | 0.6557 (2) | 0.0676 (6) | |
H8A | 0.6933 | 0.5408 | 0.7122 | 0.081* | |
H8B | 0.7578 | 0.4317 | 0.6093 | 0.081* | |
C9 | 0.6419 (3) | 0.2341 (4) | 0.7092 (2) | 0.0627 (6) | |
H9A | 0.7018 | 0.1291 | 0.6745 | 0.075* | |
H9B | 0.6796 | 0.2372 | 0.7882 | 0.075* | |
C11 | 0.1176 (3) | −0.0429 (3) | 0.76061 (19) | 0.0600 (5) | |
H11A | −0.0010 | −0.0409 | 0.7364 | 0.072* | |
H11B | 0.1455 | −0.1766 | 0.7894 | 0.072* | |
C12 | 0.1543 (2) | 0.1078 (4) | 0.85303 (16) | 0.0529 (5) | |
C13 | 0.2761 (3) | 0.0674 (5) | 0.93905 (18) | 0.0725 (7) | |
H13 | 0.3314 | −0.0557 | 0.9410 | 0.087* | |
C14 | 0.3170 (4) | 0.2047 (8) | 1.0213 (2) | 0.1006 (12) | |
H14 | 0.4005 | 0.1752 | 1.0783 | 0.121* | |
C15 | 0.2361 (5) | 0.3852 (8) | 1.0204 (3) | 0.1084 (13) | |
H15 | 0.2642 | 0.4785 | 1.0768 | 0.130* | |
C16 | 0.1145 (4) | 0.4285 (5) | 0.9371 (3) | 0.0943 (10) | |
H16 | 0.0589 | 0.5513 | 0.9369 | 0.113* | |
C17 | 0.0727 (3) | 0.2904 (4) | 0.8521 (2) | 0.0657 (6) | |
H17 | −0.0101 | 0.3211 | 0.7949 | 0.079* | |
O2 | 0.4772 (2) | −0.12931 (19) | 0.73232 (12) | 0.0591 (4) | |
O5 | 0.1418 (2) | 0.4838 (3) | 0.52975 (16) | 0.0819 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0435 (8) | 0.0363 (8) | 0.0513 (9) | 0.0044 (7) | −0.0019 (7) | 0.0065 (6) |
C2 | 0.0554 (11) | 0.0367 (10) | 0.0386 (9) | 0.0036 (9) | 0.0032 (7) | −0.0015 (7) |
C3 | 0.0587 (11) | 0.0373 (10) | 0.0481 (10) | −0.0029 (9) | −0.0051 (8) | −0.0074 (8) |
N4 | 0.0519 (10) | 0.0540 (12) | 0.0517 (9) | −0.0017 (8) | −0.0146 (8) | −0.0062 (8) |
C5 | 0.0574 (12) | 0.0458 (12) | 0.0490 (10) | 0.0112 (10) | −0.0084 (9) | −0.0002 (9) |
C6 | 0.0587 (11) | 0.0320 (9) | 0.0432 (9) | 0.0069 (8) | 0.0008 (8) | −0.0026 (7) |
C7 | 0.0806 (14) | 0.0353 (10) | 0.0535 (11) | 0.0012 (10) | 0.0109 (10) | 0.0042 (9) |
C8 | 0.0623 (13) | 0.0623 (15) | 0.0800 (15) | −0.0093 (11) | 0.0159 (11) | 0.0093 (11) |
C9 | 0.0465 (11) | 0.0591 (14) | 0.0805 (15) | −0.0010 (9) | −0.0018 (10) | 0.0131 (11) |
C11 | 0.0577 (11) | 0.0524 (12) | 0.0698 (13) | −0.0158 (10) | 0.0065 (10) | −0.0032 (11) |
C12 | 0.0446 (9) | 0.0644 (13) | 0.0515 (10) | −0.0107 (10) | 0.0130 (8) | −0.0024 (10) |
C13 | 0.0609 (13) | 0.103 (2) | 0.0532 (12) | 0.0040 (14) | 0.0068 (10) | 0.0009 (13) |
C14 | 0.0798 (19) | 0.163 (4) | 0.0577 (15) | −0.020 (2) | 0.0042 (13) | −0.0201 (19) |
C15 | 0.112 (3) | 0.143 (4) | 0.0742 (19) | −0.044 (3) | 0.0256 (19) | −0.054 (2) |
C16 | 0.103 (2) | 0.084 (2) | 0.107 (2) | −0.0099 (16) | 0.057 (2) | −0.0282 (17) |
C17 | 0.0541 (12) | 0.0740 (16) | 0.0720 (14) | −0.0040 (11) | 0.0195 (11) | −0.0029 (12) |
O2 | 0.0734 (10) | 0.0379 (8) | 0.0644 (9) | 0.0124 (7) | 0.0003 (7) | 0.0059 (7) |
O5 | 0.0813 (11) | 0.0648 (11) | 0.0911 (12) | 0.0179 (9) | −0.0278 (9) | 0.0201 (10) |
N1—C2 | 1.338 (2) | C8—H8A | 0.9700 |
N1—C9 | 1.455 (3) | C8—H8B | 0.9700 |
N1—C6 | 1.458 (2) | C9—H9A | 0.9700 |
C2—O2 | 1.220 (2) | C9—H9B | 0.9700 |
C2—C3 | 1.508 (3) | C11—C12 | 1.504 (3) |
C3—N4 | 1.451 (3) | C11—H11A | 0.9700 |
C3—C11 | 1.530 (3) | C11—H11B | 0.9700 |
C3—H3 | 0.9800 | C12—C13 | 1.376 (3) |
N4—C5 | 1.330 (3) | C12—C17 | 1.378 (4) |
N4—H4 | 0.93 (3) | C13—C14 | 1.361 (5) |
C5—O5 | 1.231 (3) | C13—H13 | 0.9300 |
C5—C6 | 1.494 (3) | C14—C15 | 1.364 (6) |
C6—C7 | 1.524 (3) | C14—H14 | 0.9300 |
C6—H6 | 0.9800 | C15—C16 | 1.356 (6) |
C7—C8 | 1.509 (4) | C15—H15 | 0.9300 |
C7—H7A | 0.9700 | C16—C17 | 1.390 (4) |
C7—H7B | 0.9700 | C16—H16 | 0.9300 |
C8—C9 | 1.524 (3) | C17—H17 | 0.9300 |
C2—N1—C9 | 122.25 (16) | C7—C8—H8B | 110.7 |
C2—N1—C6 | 126.37 (15) | C9—C8—H8B | 110.7 |
C9—N1—C6 | 111.00 (16) | H8A—C8—H8B | 108.8 |
O2—C2—N1 | 122.44 (17) | N1—C9—C8 | 104.50 (17) |
O2—C2—C3 | 120.31 (17) | N1—C9—H9A | 110.9 |
N1—C2—C3 | 117.25 (15) | C8—C9—H9A | 110.9 |
N4—C3—C2 | 113.31 (17) | N1—C9—H9B | 110.9 |
N4—C3—C11 | 112.60 (18) | C8—C9—H9B | 110.9 |
C2—C3—C11 | 109.89 (16) | H9A—C9—H9B | 108.9 |
N4—C3—H3 | 106.9 | C12—C11—C3 | 113.89 (17) |
C2—C3—H3 | 106.9 | C12—C11—H11A | 108.8 |
C11—C3—H3 | 106.9 | C3—C11—H11A | 108.8 |
C5—N4—C3 | 126.96 (17) | C12—C11—H11B | 108.8 |
C5—N4—H4 | 118.9 (17) | C3—C11—H11B | 108.8 |
C3—N4—H4 | 114.2 (17) | H11A—C11—H11B | 107.7 |
O5—C5—N4 | 123.26 (19) | C13—C12—C17 | 118.6 (2) |
O5—C5—C6 | 119.2 (2) | C13—C12—C11 | 119.8 (2) |
N4—C5—C6 | 117.51 (17) | C17—C12—C11 | 121.6 (2) |
N1—C6—C5 | 113.93 (16) | C14—C13—C12 | 121.1 (3) |
N1—C6—C7 | 101.38 (16) | C14—C13—H13 | 119.4 |
C5—C6—C7 | 115.29 (16) | C12—C13—H13 | 119.4 |
N1—C6—H6 | 108.6 | C13—C14—C15 | 120.3 (3) |
C5—C6—H6 | 108.6 | C13—C14—H14 | 119.9 |
C7—C6—H6 | 108.6 | C15—C14—H14 | 119.9 |
C8—C7—C6 | 103.41 (16) | C16—C15—C14 | 119.9 (3) |
C8—C7—H7A | 111.1 | C16—C15—H15 | 120.1 |
C6—C7—H7A | 111.1 | C14—C15—H15 | 120.1 |
C8—C7—H7B | 111.1 | C15—C16—C17 | 120.3 (4) |
C6—C7—H7B | 111.1 | C15—C16—H16 | 119.8 |
H7A—C7—H7B | 109.0 | C17—C16—H16 | 119.8 |
C7—C8—C9 | 105.24 (18) | C12—C17—C16 | 119.8 (3) |
C7—C8—H8A | 110.7 | C12—C17—H17 | 120.1 |
C9—C8—H8A | 110.7 | C16—C17—H17 | 120.1 |
C9—N1—C2—O2 | 8.7 (3) | N4—C5—C6—C7 | 131.7 (2) |
C6—N1—C2—O2 | −179.07 (17) | N1—C6—C7—C8 | −37.70 (19) |
C9—N1—C2—C3 | −171.49 (19) | C5—C6—C7—C8 | −161.25 (18) |
C6—N1—C2—C3 | 0.8 (3) | C6—C7—C8—C9 | 31.5 (2) |
O2—C2—C3—N4 | −163.51 (17) | C2—N1—C9—C8 | 161.35 (19) |
N1—C2—C3—N4 | 16.6 (2) | C6—N1—C9—C8 | −12.0 (2) |
O2—C2—C3—C11 | 69.6 (2) | C7—C8—C9—N1 | −12.8 (2) |
N1—C2—C3—C11 | −110.3 (2) | N4—C3—C11—C12 | −75.2 (2) |
C2—C3—N4—C5 | −19.2 (3) | C2—C3—C11—C12 | 52.2 (2) |
C11—C3—N4—C5 | 106.3 (2) | C3—C11—C12—C13 | −93.9 (3) |
C3—N4—C5—O5 | −177.2 (2) | C3—C11—C12—C17 | 83.8 (3) |
C3—N4—C5—C6 | 2.9 (3) | C17—C12—C13—C14 | −0.6 (4) |
C2—N1—C6—C5 | −17.2 (3) | C11—C12—C13—C14 | 177.1 (2) |
C9—N1—C6—C5 | 155.78 (18) | C12—C13—C14—C15 | 0.7 (5) |
C2—N1—C6—C7 | −141.70 (18) | C13—C14—C15—C16 | −0.2 (5) |
C9—N1—C6—C7 | 31.3 (2) | C14—C15—C16—C17 | −0.4 (5) |
O5—C5—C6—N1 | −164.9 (2) | C13—C12—C17—C16 | 0.0 (3) |
N4—C5—C6—N1 | 15.0 (3) | C11—C12—C17—C16 | −177.7 (2) |
O5—C5—C6—C7 | −48.3 (3) | C15—C16—C17—C12 | 0.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4···O5i | 0.93 (3) | 1.97 (3) | 2.859 (2) | 161 (2) |
C7—H7B···O2ii | 0.97 | 2.45 | 3.133 (2) | 128 |
Symmetry codes: (i) −x, y−1/2, −z+1; (ii) x, y+1, z. |
C15H18N2O2 | Dx = 1.306 Mg m−3 |
Mr = 258.31 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43212 | Cell parameters from 3032 reflections |
Hall symbol: P 4nw 2abw | θ = 3–27.5° |
a = 7.8284 (2) Å | µ = 0.09 mm−1 |
c = 42.8636 (9) Å | T = 150 K |
V = 2626.85 (11) Å3 | Prism, colourless |
Z = 8 | 0.4 × 0.3 × 0.1 mm |
F(000) = 1104 |
Nonius KappaCCD area detector diffractometer | 2402 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.055 |
Graphite monochromator | θmax = 27.5°, θmin = 3.0° |
Detector resolution: 9.091 pixels mm-1 | h = −10→10 |
φ and ω scans to fill the Ewald sphere | k = −7→7 |
24574 measured reflections | l = −55→55 |
2994 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.039 | H-atom parameters constrained |
wR(F2) = 0.091 | w = 1/[σ2(Fo2) + (0.0388P)2 + 0.3491P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
2994 reflections | Δρmax = 0.14 e Å−3 |
173 parameters | Δρmin = −0.14 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 1.5 (14) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.52102 (16) | 0.89914 (16) | 0.77171 (3) | 0.0303 (3) | |
C2 | 0.3547 (2) | 0.9272 (2) | 0.77700 (3) | 0.0288 (3) | |
C3 | 0.2535 (2) | 0.78621 (19) | 0.79282 (3) | 0.0285 (3) | |
H3 | 0.1491 | 0.7688 | 0.7806 | 0.034* | |
N4 | 0.34033 (16) | 0.62127 (16) | 0.79491 (3) | 0.0291 (3) | |
C5 | 0.5122 (2) | 0.6021 (2) | 0.79406 (4) | 0.0312 (4) | |
C6 | 0.61582 (19) | 0.7460 (2) | 0.78063 (3) | 0.0303 (4) | |
H6 | 0.6708 | 0.7024 | 0.7617 | 0.036* | |
C7 | 0.7568 (2) | 0.8180 (2) | 0.80133 (4) | 0.0348 (4) | |
H7A | 0.8555 | 0.7432 | 0.8016 | 0.042* | |
H7B | 0.7167 | 0.8349 | 0.8225 | 0.042* | |
C8 | 0.7992 (2) | 0.9893 (2) | 0.78562 (4) | 0.0393 (4) | |
H8A | 0.8249 | 1.0753 | 0.8012 | 0.047* | |
H8B | 0.8974 | 0.9770 | 0.7720 | 0.047* | |
C9 | 0.6419 (2) | 1.0407 (2) | 0.76683 (4) | 0.0407 (4) | |
H9A | 0.5948 | 1.1475 | 0.7744 | 0.049* | |
H9B | 0.6697 | 1.0531 | 0.7449 | 0.049* | |
C10 | 0.19918 (19) | 0.8534 (2) | 0.82535 (3) | 0.0315 (4) | |
H10A | 0.1315 | 0.9561 | 0.8226 | 0.038* | |
H10B | 0.1272 | 0.7685 | 0.8353 | 0.038* | |
C11 | 0.3475 (2) | 0.8930 (2) | 0.84658 (3) | 0.0295 (3) | |
C12 | 0.4206 (2) | 1.0551 (2) | 0.84702 (4) | 0.0352 (4) | |
H12 | 0.3784 | 1.1396 | 0.8339 | 0.042* | |
C13 | 0.5551 (2) | 1.0918 (3) | 0.86676 (4) | 0.0441 (4) | |
H13 | 0.6024 | 1.2007 | 0.8668 | 0.053* | |
C14 | 0.6198 (2) | 0.9688 (3) | 0.88642 (4) | 0.0470 (5) | |
H14 | 0.7096 | 0.9946 | 0.8998 | 0.056* | |
C15 | 0.5501 (2) | 0.8069 (3) | 0.88607 (4) | 0.0427 (4) | |
H15 | 0.5938 | 0.7229 | 0.8992 | 0.051* | |
C16 | 0.4154 (2) | 0.7692 (2) | 0.86631 (3) | 0.0337 (4) | |
H16 | 0.3696 | 0.6595 | 0.8662 | 0.040* | |
C17 | 0.2369 (2) | 0.4768 (2) | 0.80538 (4) | 0.0380 (4) | |
H17A | 0.2429 | 0.4681 | 0.8277 | 0.057* | |
H17B | 0.2795 | 0.3734 | 0.7962 | 0.057* | |
H17C | 0.1203 | 0.4939 | 0.7992 | 0.057* | |
O2 | 0.28202 (15) | 1.06203 (14) | 0.77088 (3) | 0.0387 (3) | |
O5 | 0.58386 (16) | 0.46897 (15) | 0.80183 (3) | 0.0437 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0288 (7) | 0.0315 (7) | 0.0307 (6) | −0.0035 (6) | −0.0019 (5) | 0.0043 (6) |
C2 | 0.0285 (8) | 0.0329 (9) | 0.0249 (7) | −0.0029 (7) | −0.0042 (6) | 0.0022 (6) |
C3 | 0.0252 (8) | 0.0319 (8) | 0.0283 (7) | −0.0019 (7) | −0.0032 (6) | 0.0030 (6) |
N4 | 0.0292 (7) | 0.0276 (7) | 0.0305 (6) | −0.0032 (5) | 0.0008 (5) | 0.0020 (5) |
C5 | 0.0330 (9) | 0.0322 (9) | 0.0284 (8) | 0.0029 (7) | −0.0014 (6) | −0.0012 (7) |
C6 | 0.0275 (8) | 0.0334 (9) | 0.0301 (7) | 0.0035 (7) | 0.0017 (6) | 0.0005 (7) |
C7 | 0.0266 (8) | 0.0450 (10) | 0.0329 (8) | −0.0013 (7) | −0.0015 (7) | 0.0006 (7) |
C8 | 0.0313 (9) | 0.0452 (10) | 0.0414 (9) | −0.0082 (8) | 0.0008 (7) | −0.0010 (8) |
C9 | 0.0352 (10) | 0.0438 (11) | 0.0431 (9) | −0.0131 (8) | −0.0014 (8) | 0.0090 (8) |
C10 | 0.0251 (8) | 0.0390 (10) | 0.0303 (8) | 0.0006 (7) | 0.0004 (6) | 0.0020 (7) |
C11 | 0.0243 (8) | 0.0368 (9) | 0.0273 (7) | 0.0019 (7) | 0.0038 (6) | −0.0033 (7) |
C12 | 0.0312 (9) | 0.0362 (9) | 0.0380 (9) | 0.0022 (8) | 0.0028 (7) | −0.0060 (7) |
C13 | 0.0318 (10) | 0.0469 (11) | 0.0537 (10) | −0.0047 (8) | 0.0045 (8) | −0.0218 (9) |
C14 | 0.0292 (9) | 0.0750 (14) | 0.0367 (9) | −0.0001 (9) | −0.0030 (7) | −0.0204 (10) |
C15 | 0.0354 (10) | 0.0649 (13) | 0.0278 (8) | 0.0099 (9) | −0.0001 (7) | 0.0001 (8) |
C16 | 0.0302 (8) | 0.0430 (10) | 0.0280 (7) | 0.0024 (8) | 0.0037 (6) | 0.0000 (7) |
C17 | 0.0417 (10) | 0.0345 (9) | 0.0380 (8) | −0.0104 (8) | 0.0002 (8) | 0.0033 (7) |
O2 | 0.0355 (7) | 0.0359 (7) | 0.0447 (6) | 0.0015 (5) | −0.0061 (5) | 0.0103 (6) |
O5 | 0.0424 (7) | 0.0347 (7) | 0.0539 (7) | 0.0057 (6) | −0.0038 (6) | 0.0045 (6) |
N1—C2 | 1.340 (2) | C9—H9A | 0.9700 |
N1—C6 | 1.4607 (19) | C9—H9B | 0.9700 |
N1—C9 | 1.472 (2) | C10—C11 | 1.507 (2) |
C2—O2 | 1.2275 (18) | C10—H10A | 0.9700 |
C2—C3 | 1.518 (2) | C10—H10B | 0.9700 |
C3—N4 | 1.4618 (19) | C11—C12 | 1.392 (2) |
C3—C10 | 1.550 (2) | C11—C16 | 1.392 (2) |
C3—H3 | 0.9800 | C12—C13 | 1.381 (2) |
N4—C5 | 1.354 (2) | C12—H12 | 0.9300 |
N4—C17 | 1.462 (2) | C13—C14 | 1.376 (3) |
C5—O5 | 1.2295 (19) | C13—H13 | 0.9300 |
C5—C6 | 1.503 (2) | C14—C15 | 1.380 (3) |
C6—C7 | 1.524 (2) | C14—H14 | 0.9300 |
C6—H6 | 0.9800 | C15—C16 | 1.385 (2) |
C7—C8 | 1.537 (2) | C15—H15 | 0.9300 |
C7—H7A | 0.9700 | C16—H16 | 0.9300 |
C7—H7B | 0.9700 | C17—H17A | 0.9600 |
C8—C9 | 1.526 (2) | C17—H17B | 0.9600 |
C8—H8A | 0.9700 | C17—H17C | 0.9600 |
C8—H8B | 0.9700 | ||
C2—N1—C6 | 125.73 (13) | N1—C9—C8 | 104.18 (13) |
C2—N1—C9 | 121.68 (14) | N1—C9—H9A | 110.9 |
C6—N1—C9 | 109.18 (12) | C8—C9—H9A | 110.9 |
O2—C2—N1 | 123.72 (14) | N1—C9—H9B | 110.9 |
O2—C2—C3 | 118.61 (14) | C8—C9—H9B | 110.9 |
N1—C2—C3 | 117.61 (14) | H9A—C9—H9B | 108.9 |
N4—C3—C2 | 115.28 (13) | C11—C10—C3 | 113.67 (13) |
N4—C3—C10 | 111.84 (12) | C11—C10—H10A | 108.8 |
C2—C3—C10 | 107.37 (13) | C3—C10—H10A | 108.8 |
N4—C3—H3 | 107.3 | C11—C10—H10B | 108.8 |
C2—C3—H3 | 107.3 | C3—C10—H10B | 108.8 |
C10—C3—H3 | 107.3 | H10A—C10—H10B | 107.7 |
C5—N4—C3 | 123.93 (13) | C12—C11—C16 | 118.00 (15) |
C5—N4—C17 | 118.21 (14) | C12—C11—C10 | 120.84 (15) |
C3—N4—C17 | 116.42 (13) | C16—C11—C10 | 121.16 (15) |
O5—C5—N4 | 122.70 (16) | C13—C12—C11 | 120.76 (17) |
O5—C5—C6 | 119.51 (15) | C13—C12—H12 | 119.6 |
N4—C5—C6 | 117.61 (14) | C11—C12—H12 | 119.6 |
N1—C6—C5 | 116.17 (12) | C14—C13—C12 | 120.70 (18) |
N1—C6—C7 | 102.52 (13) | C14—C13—H13 | 119.7 |
C5—C6—C7 | 116.44 (13) | C12—C13—H13 | 119.7 |
N1—C6—H6 | 107.0 | C13—C14—C15 | 119.36 (17) |
C5—C6—H6 | 107.0 | C13—C14—H14 | 120.3 |
C7—C6—H6 | 107.0 | C15—C14—H14 | 120.3 |
C6—C7—C8 | 102.94 (13) | C14—C15—C16 | 120.26 (17) |
C6—C7—H7A | 111.2 | C14—C15—H15 | 119.9 |
C8—C7—H7A | 111.2 | C16—C15—H15 | 119.9 |
C6—C7—H7B | 111.2 | C15—C16—C11 | 120.92 (17) |
C8—C7—H7B | 111.2 | C15—C16—H16 | 119.5 |
H7A—C7—H7B | 109.1 | C11—C16—H16 | 119.5 |
C9—C8—C7 | 106.69 (13) | N4—C17—H17A | 109.5 |
C9—C8—H8A | 110.4 | N4—C17—H17B | 109.5 |
C7—C8—H8A | 110.4 | H17A—C17—H17B | 109.5 |
C9—C8—H8B | 110.4 | N4—C17—H17C | 109.5 |
C7—C8—H8B | 110.4 | H17A—C17—H17C | 109.5 |
H8A—C8—H8B | 108.6 | H17B—C17—H17C | 109.5 |
C15H18N2O2 | F(000) = 552 |
Mr = 258.31 | Dx = 1.277 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 1784 reflections |
a = 10.1348 (4) Å | θ = 1–27.5° |
b = 10.9014 (3) Å | µ = 0.09 mm−1 |
c = 12.1599 (4) Å | T = 150 K |
V = 1343.47 (8) Å3 | Prism, colourless |
Z = 4 | 0.35 × 0.3 × 0.25 mm |
Nonius KappaCCD area detector diffractometer | 2577 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 27.5°, θmin = 2.5° |
Detector resolution: 9.091 pixels mm-1 | h = −13→13 |
φ and ω scans to fill the Ewald sphere | k = −14→14 |
11846 measured reflections | l = −15→15 |
3071 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.036 | H-atom parameters constrained |
wR(F2) = 0.085 | w = 1/[σ2(Fo2) + (0.0503P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max < 0.001 |
3071 reflections | Δρmax = 0.13 e Å−3 |
173 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.0 (10) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.22471 (12) | 0.77530 (9) | 0.07886 (8) | 0.0280 (3) | |
C2 | 0.28151 (14) | 0.87308 (11) | 0.12512 (10) | 0.0268 (3) | |
C3 | 0.35221 (13) | 0.85174 (11) | 0.23322 (10) | 0.0259 (3) | |
H3 | 0.4328 | 0.9047 | 0.2318 | 0.031* | |
N4 | 0.39891 (11) | 0.72480 (10) | 0.24597 (8) | 0.0257 (2) | |
C5 | 0.34112 (13) | 0.62720 (11) | 0.19868 (10) | 0.0265 (3) | |
C6 | 0.22360 (14) | 0.65206 (11) | 0.12583 (10) | 0.0266 (3) | |
H6 | 0.1413 | 0.6416 | 0.1702 | 0.032* | |
C7 | 0.21393 (16) | 0.57201 (12) | 0.02345 (11) | 0.0352 (3) | |
H7A | 0.1770 | 0.4902 | 0.0409 | 0.042* | |
H7B | 0.3010 | 0.5618 | −0.0122 | 0.042* | |
C8 | 0.11994 (16) | 0.64638 (14) | −0.04848 (11) | 0.0406 (4) | |
H8A | 0.0272 | 0.6337 | −0.0256 | 0.049* | |
H8B | 0.1292 | 0.6233 | −0.1268 | 0.049* | |
C9 | 0.16223 (17) | 0.77920 (14) | −0.02988 (11) | 0.0405 (4) | |
H9A | 0.2255 | 0.8063 | −0.0869 | 0.049* | |
H9B | 0.0851 | 0.8350 | −0.0301 | 0.049* | |
C10 | 0.50917 (15) | 0.70452 (14) | 0.32134 (12) | 0.0382 (4) | |
H10A | 0.4756 | 0.6731 | 0.3915 | 0.057* | |
H10B | 0.5556 | 0.7821 | 0.3338 | 0.057* | |
H10C | 0.5702 | 0.6447 | 0.2892 | 0.057* | |
C11 | 0.26810 (14) | 0.89624 (12) | 0.33153 (10) | 0.0299 (3) | |
H11A | 0.3186 | 0.8833 | 0.4003 | 0.036* | |
H11B | 0.2524 | 0.9854 | 0.3237 | 0.036* | |
C12 | 0.13761 (13) | 0.83217 (12) | 0.34128 (10) | 0.0275 (3) | |
C13 | 0.02642 (14) | 0.87856 (12) | 0.28909 (12) | 0.0341 (3) | |
H13 | 0.0324 | 0.9535 | 0.2496 | 0.041* | |
C14 | −0.09319 (16) | 0.81719 (15) | 0.29372 (13) | 0.0418 (4) | |
H14 | −0.1683 | 0.8500 | 0.2574 | 0.050* | |
C15 | −0.10320 (16) | 0.70808 (13) | 0.35133 (12) | 0.0402 (4) | |
H15 | −0.1851 | 0.6658 | 0.3548 | 0.048* | |
C16 | 0.00629 (15) | 0.66102 (13) | 0.40370 (12) | 0.0380 (3) | |
H16 | −0.0001 | 0.5858 | 0.4427 | 0.046* | |
C17 | 0.12553 (14) | 0.72285 (12) | 0.39969 (10) | 0.0319 (3) | |
H17 | 0.1999 | 0.6903 | 0.4372 | 0.038* | |
O2 | 0.27815 (11) | 0.97623 (8) | 0.08400 (8) | 0.0371 (3) | |
O5 | 0.37901 (10) | 0.52100 (8) | 0.21342 (8) | 0.0388 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0315 (6) | 0.0263 (5) | 0.0262 (5) | 0.0022 (5) | −0.0049 (5) | 0.0002 (4) |
C2 | 0.0261 (7) | 0.0257 (7) | 0.0285 (6) | 0.0039 (6) | 0.0044 (5) | −0.0013 (5) |
C3 | 0.0253 (7) | 0.0230 (6) | 0.0293 (6) | −0.0022 (6) | 0.0005 (5) | −0.0023 (5) |
N4 | 0.0239 (6) | 0.0272 (5) | 0.0260 (5) | 0.0018 (5) | −0.0042 (5) | −0.0018 (4) |
C5 | 0.0273 (7) | 0.0260 (6) | 0.0262 (6) | −0.0003 (6) | −0.0005 (6) | 0.0001 (5) |
C6 | 0.0267 (7) | 0.0246 (6) | 0.0284 (6) | −0.0003 (6) | −0.0008 (5) | −0.0004 (5) |
C7 | 0.0397 (8) | 0.0320 (7) | 0.0338 (7) | −0.0016 (7) | −0.0036 (6) | −0.0063 (6) |
C8 | 0.0412 (9) | 0.0493 (9) | 0.0314 (7) | −0.0028 (8) | −0.0096 (6) | −0.0074 (6) |
C9 | 0.0470 (9) | 0.0418 (8) | 0.0328 (8) | 0.0086 (7) | −0.0149 (7) | −0.0006 (6) |
C10 | 0.0324 (9) | 0.0427 (8) | 0.0396 (8) | 0.0008 (7) | −0.0104 (6) | 0.0009 (7) |
C11 | 0.0290 (8) | 0.0313 (7) | 0.0296 (7) | −0.0011 (6) | 0.0021 (6) | −0.0069 (5) |
C12 | 0.0286 (7) | 0.0282 (6) | 0.0258 (6) | 0.0007 (6) | 0.0045 (5) | −0.0072 (5) |
C13 | 0.0319 (8) | 0.0285 (7) | 0.0418 (8) | 0.0029 (6) | 0.0032 (7) | 0.0019 (6) |
C14 | 0.0293 (8) | 0.0445 (9) | 0.0515 (9) | 0.0031 (7) | −0.0035 (7) | −0.0032 (7) |
C15 | 0.0337 (9) | 0.0362 (8) | 0.0506 (9) | −0.0062 (7) | 0.0090 (7) | −0.0098 (7) |
C16 | 0.0452 (9) | 0.0300 (7) | 0.0389 (7) | −0.0029 (7) | 0.0141 (7) | 0.0003 (6) |
C17 | 0.0340 (8) | 0.0337 (7) | 0.0281 (6) | 0.0028 (6) | 0.0033 (6) | 0.0005 (6) |
O2 | 0.0453 (6) | 0.0256 (5) | 0.0404 (6) | 0.0037 (5) | −0.0013 (5) | 0.0057 (4) |
O5 | 0.0415 (6) | 0.0249 (5) | 0.0499 (6) | 0.0039 (4) | −0.0122 (5) | 0.0033 (4) |
N1—C2 | 1.3357 (16) | C9—H9A | 0.9900 |
N1—C6 | 1.4598 (16) | C9—H9B | 0.9900 |
N1—C9 | 1.4667 (17) | C10—H10A | 0.9800 |
C2—O2 | 1.2311 (15) | C10—H10B | 0.9800 |
C2—C3 | 1.5151 (18) | C10—H10C | 0.9800 |
C3—N4 | 1.4707 (16) | C11—C12 | 1.500 (2) |
C3—C11 | 1.5463 (18) | C11—H11A | 0.9900 |
C3—H3 | 1.0000 | C11—H11B | 0.9900 |
N4—C5 | 1.3437 (16) | C12—C13 | 1.3887 (19) |
N4—C10 | 1.4621 (17) | C12—C17 | 1.3928 (19) |
C5—O5 | 1.2328 (15) | C13—C14 | 1.386 (2) |
C5—C6 | 1.5089 (18) | C13—H13 | 0.9500 |
C6—C7 | 1.5235 (17) | C14—C15 | 1.384 (2) |
C6—H6 | 1.0000 | C14—H14 | 0.9500 |
C7—C8 | 1.526 (2) | C15—C16 | 1.378 (2) |
C7—H7A | 0.9900 | C15—H15 | 0.9500 |
C7—H7B | 0.9900 | C16—C17 | 1.385 (2) |
C8—C9 | 1.527 (2) | C16—H16 | 0.9500 |
C8—H8A | 0.9900 | C17—H17 | 0.9500 |
C8—H8B | 0.9900 | ||
C2—N1—C6 | 124.96 (10) | N1—C9—C8 | 103.13 (11) |
C2—N1—C9 | 122.86 (11) | N1—C9—H9A | 111.1 |
C6—N1—C9 | 112.09 (10) | C8—C9—H9A | 111.1 |
O2—C2—N1 | 123.09 (12) | N1—C9—H9B | 111.1 |
O2—C2—C3 | 120.38 (11) | C8—C9—H9B | 111.1 |
N1—C2—C3 | 116.53 (11) | H9A—C9—H9B | 109.1 |
N4—C3—C2 | 112.84 (10) | N4—C10—H10A | 109.5 |
N4—C3—C11 | 113.03 (10) | N4—C10—H10B | 109.5 |
C2—C3—C11 | 111.21 (11) | H10A—C10—H10B | 109.5 |
N4—C3—H3 | 106.4 | N4—C10—H10C | 109.5 |
C2—C3—H3 | 106.4 | H10A—C10—H10C | 109.5 |
C11—C3—H3 | 106.4 | H10B—C10—H10C | 109.5 |
C5—N4—C10 | 118.79 (11) | C12—C11—C3 | 113.64 (10) |
C5—N4—C3 | 124.03 (10) | C12—C11—H11A | 108.8 |
C10—N4—C3 | 117.02 (10) | C3—C11—H11A | 108.8 |
O5—C5—N4 | 123.06 (12) | C12—C11—H11B | 108.8 |
O5—C5—C6 | 119.99 (11) | C3—C11—H11B | 108.8 |
N4—C5—C6 | 116.94 (11) | H11A—C11—H11B | 107.7 |
N1—C6—C5 | 112.88 (11) | C13—C12—C17 | 118.25 (13) |
N1—C6—C7 | 102.00 (10) | C13—C12—C11 | 120.64 (12) |
C5—C6—C7 | 115.31 (11) | C17—C12—C11 | 121.08 (12) |
N1—C6—H6 | 108.8 | C14—C13—C12 | 121.03 (13) |
C5—C6—H6 | 108.8 | C14—C13—H13 | 119.5 |
C7—C6—H6 | 108.8 | C12—C13—H13 | 119.5 |
C6—C7—C8 | 101.78 (11) | C15—C14—C13 | 119.97 (15) |
C6—C7—H7A | 111.4 | C15—C14—H14 | 120.0 |
C8—C7—H7A | 111.4 | C13—C14—H14 | 120.0 |
C6—C7—H7B | 111.4 | C16—C15—C14 | 119.64 (14) |
C8—C7—H7B | 111.4 | C16—C15—H15 | 120.2 |
H7A—C7—H7B | 109.3 | C14—C15—H15 | 120.2 |
C7—C8—C9 | 104.10 (11) | C15—C16—C17 | 120.34 (13) |
C7—C8—H8A | 110.9 | C15—C16—H16 | 119.8 |
C9—C8—H8A | 110.9 | C17—C16—H16 | 119.8 |
C7—C8—H8B | 110.9 | C16—C17—C12 | 120.75 (13) |
C9—C8—H8B | 110.9 | C16—C17—H17 | 119.6 |
H8A—C8—H8B | 109.0 | C12—C17—H17 | 119.6 |
C6—N1—C2—O2 | −178.52 (12) | N4—C5—C6—N1 | 25.59 (16) |
C9—N1—C2—O2 | 5.2 (2) | O5—C5—C6—C7 | −38.49 (18) |
C6—N1—C2—C3 | 1.45 (19) | N4—C5—C6—C7 | 142.29 (12) |
C9—N1—C2—C3 | −174.81 (13) | N1—C6—C7—C8 | −38.38 (14) |
O2—C2—C3—N4 | −154.04 (12) | C5—C6—C7—C8 | −161.09 (11) |
N1—C2—C3—N4 | 25.99 (17) | C6—C7—C8—C9 | 39.55 (15) |
O2—C2—C3—C11 | 77.73 (15) | C2—N1—C9—C8 | 176.95 (13) |
N1—C2—C3—C11 | −102.23 (13) | C6—N1—C9—C8 | 0.26 (16) |
C2—C3—N4—C5 | −28.21 (17) | C7—C8—C9—N1 | −24.88 (15) |
C11—C3—N4—C5 | 99.06 (14) | N4—C3—C11—C12 | −67.73 (14) |
C2—C3—N4—C10 | 156.38 (11) | C2—C3—C11—C12 | 60.39 (14) |
C11—C3—N4—C10 | −76.35 (14) | C3—C11—C12—C13 | −90.29 (15) |
C10—N4—C5—O5 | −2.08 (19) | C3—C11—C12—C17 | 87.61 (15) |
C3—N4—C5—O5 | −177.40 (12) | C17—C12—C13—C14 | −0.8 (2) |
C10—N4—C5—C6 | 177.12 (11) | C11—C12—C13—C14 | 177.19 (12) |
C3—N4—C5—C6 | 1.79 (17) | C12—C13—C14—C15 | 0.2 (2) |
C2—N1—C6—C5 | −27.96 (18) | C13—C14—C15—C16 | −0.1 (2) |
C9—N1—C6—C5 | 148.65 (12) | C14—C15—C16—C17 | 0.6 (2) |
C2—N1—C6—C7 | −152.31 (13) | C15—C16—C17—C12 | −1.1 (2) |
C9—N1—C6—C7 | 24.30 (15) | C13—C12—C17—C16 | 1.2 (2) |
O5—C5—C6—N1 | −155.19 (12) | C11—C12—C17—C16 | −176.72 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O5i | 1.00 | 2.39 | 3.3536 (16) | 163 |
C8—H8B···O5ii | 0.99 | 2.50 | 3.4224 (17) | 155 |
C15—H15···O2iii | 0.95 | 2.39 | 3.1859 (18) | 141 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) −x+1/2, −y+1, z−1/2; (iii) −x, y−1/2, −z+1/2. |
C15H18N2O2 | F(000) = 552 |
Mr = 258.31 | Dx = 1.255 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 10.1490 (5) Å | θ = 13–14° |
b = 10.939 (1) Å | µ = 0.08 mm−1 |
c = 12.310 (1) Å | T = 293 K |
V = 1366.66 (18) Å3 | Prism, colourless |
Z = 4 | 0.5 × 0.4 × 0.3 mm |
CAD4-MACHIII diffractometer | Rint = 0.0000 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.5° |
Graphite monochromator | h = 0→12 |
θ–2θ scan | k = 0→12 |
1386 measured reflections | l = 0→14 |
1386 independent reflections | 3 standard reflections every 3600 min |
1179 reflections with I > 2σ(I) | intensity decay: 9% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.035 | w = 1/[σ2(Fo2) + (0.0678P)2 + 0.0829P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.101 | (Δ/σ)max < 0.001 |
S = 1.07 | Δρmax = 0.13 e Å−3 |
1386 reflections | Δρmin = −0.17 e Å−3 |
174 parameters | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.028 (4) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack H D (1983), Acta Cryst. A39, 876-881 |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −3 (2) |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.7752 (2) | 0.22607 (17) | 0.08058 (15) | 0.0458 (5) | |
C2 | 0.7183 (2) | 0.1294 (2) | 0.12611 (18) | 0.0436 (5) | |
C3 | 0.6482 (2) | 0.1502 (2) | 0.23244 (17) | 0.0407 (5) | |
H3 | 0.5692 | 0.0987 | 0.2307 | 0.049* | |
N4 | 0.60164 (18) | 0.27640 (17) | 0.24587 (15) | 0.0414 (5) | |
C5 | 0.6589 (2) | 0.37307 (19) | 0.19856 (17) | 0.0426 (5) | |
C6 | 0.7752 (2) | 0.3487 (2) | 0.12667 (17) | 0.0418 (5) | |
H6 | 0.8558 | 0.3593 | 0.1695 | 0.050* | |
C7 | 0.7849 (3) | 0.4282 (3) | 0.0261 (2) | 0.0617 (7) | |
H7A | 0.8218 | 0.5077 | 0.0430 | 0.074* | |
H7B | 0.6995 | 0.4388 | −0.0080 | 0.074* | |
C8 | 0.8772 (3) | 0.3541 (3) | −0.0454 (2) | 0.0749 (9) | |
H8A | 0.8658 | 0.3756 | −0.1213 | 0.090* | |
H8B | 0.9683 | 0.3679 | −0.0251 | 0.090* | |
C9 | 0.8384 (4) | 0.2230 (3) | −0.0256 (2) | 0.0712 (9) | |
H9A | 0.7777 | 0.1945 | −0.0809 | 0.085* | |
H9B | 0.9152 | 0.1702 | −0.0248 | 0.085* | |
C10 | 0.4911 (3) | 0.2955 (3) | 0.3195 (2) | 0.0633 (8) | |
H10A | 0.5231 | 0.3261 | 0.3876 | 0.095* | |
H10B | 0.4461 | 0.2194 | 0.3310 | 0.095* | |
H10C | 0.4313 | 0.3537 | 0.2882 | 0.095* | |
C11 | 0.7314 (3) | 0.1047 (2) | 0.32916 (19) | 0.0496 (6) | |
H11A | 0.6816 | 0.1164 | 0.3956 | 0.060* | |
H11B | 0.7470 | 0.0178 | 0.3207 | 0.060* | |
C12 | 0.8618 (2) | 0.1688 (2) | 0.34005 (17) | 0.0428 (5) | |
C13 | 0.9728 (3) | 0.1243 (2) | 0.2894 (2) | 0.0592 (7) | |
H13 | 0.9678 | 0.0516 | 0.2505 | 0.071* | |
C14 | 1.0913 (3) | 0.1855 (3) | 0.2953 (3) | 0.0720 (9) | |
H14 | 1.1651 | 0.1544 | 0.2601 | 0.086* | |
C15 | 1.1002 (3) | 0.2922 (3) | 0.3531 (3) | 0.0705 (9) | |
H15 | 1.1801 | 0.3336 | 0.3574 | 0.085* | |
C16 | 0.9924 (3) | 0.3370 (3) | 0.4039 (3) | 0.0643 (8) | |
H16 | 0.9984 | 0.4098 | 0.4427 | 0.077* | |
C17 | 0.8738 (3) | 0.2763 (2) | 0.3988 (2) | 0.0525 (6) | |
H17 | 0.8010 | 0.3078 | 0.4351 | 0.063* | |
O2 | 0.7219 (2) | 0.02684 (15) | 0.08536 (16) | 0.0649 (5) | |
O5 | 0.6212 (2) | 0.47820 (15) | 0.21331 (18) | 0.0678 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0551 (11) | 0.0403 (10) | 0.0422 (9) | 0.0052 (10) | 0.0092 (10) | −0.0014 (8) |
C2 | 0.0438 (12) | 0.0370 (12) | 0.0500 (12) | 0.0052 (10) | −0.0078 (11) | −0.0004 (10) |
C3 | 0.0386 (11) | 0.0344 (11) | 0.0493 (12) | −0.0036 (10) | −0.0003 (10) | 0.0044 (10) |
N4 | 0.0394 (10) | 0.0392 (10) | 0.0455 (9) | 0.0018 (8) | 0.0081 (9) | 0.0032 (8) |
C5 | 0.0456 (12) | 0.0356 (11) | 0.0467 (11) | 0.0023 (10) | 0.0037 (11) | −0.0012 (10) |
C6 | 0.0440 (11) | 0.0365 (11) | 0.0448 (11) | −0.0015 (10) | 0.0016 (10) | 0.0024 (9) |
C7 | 0.0732 (17) | 0.0535 (16) | 0.0585 (14) | −0.0039 (15) | 0.0090 (14) | 0.0137 (13) |
C8 | 0.080 (2) | 0.091 (2) | 0.0539 (14) | −0.0059 (19) | 0.0225 (15) | 0.0140 (16) |
C9 | 0.087 (2) | 0.0691 (18) | 0.0576 (16) | 0.0122 (17) | 0.0285 (16) | 0.0005 (14) |
C10 | 0.0540 (16) | 0.0665 (18) | 0.0693 (16) | 0.0024 (13) | 0.0202 (14) | 0.0009 (15) |
C11 | 0.0515 (14) | 0.0445 (13) | 0.0529 (13) | −0.0043 (12) | −0.0023 (12) | 0.0141 (11) |
C12 | 0.0469 (13) | 0.0400 (11) | 0.0414 (11) | 0.0015 (11) | −0.0083 (10) | 0.0122 (10) |
C13 | 0.0546 (15) | 0.0444 (13) | 0.0786 (18) | 0.0057 (12) | −0.0073 (14) | −0.0042 (14) |
C14 | 0.0474 (15) | 0.073 (2) | 0.096 (2) | 0.0067 (14) | 0.0045 (16) | 0.0058 (18) |
C15 | 0.0549 (16) | 0.0633 (19) | 0.093 (2) | −0.0131 (15) | −0.0182 (17) | 0.0205 (17) |
C16 | 0.0744 (19) | 0.0496 (14) | 0.0690 (16) | −0.0070 (15) | −0.0271 (16) | −0.0015 (14) |
C17 | 0.0577 (15) | 0.0536 (13) | 0.0463 (12) | 0.0067 (12) | −0.0066 (12) | −0.0011 (11) |
O2 | 0.0840 (13) | 0.0387 (10) | 0.0720 (12) | 0.0076 (9) | 0.0027 (12) | −0.0119 (9) |
O5 | 0.0770 (13) | 0.0369 (9) | 0.0896 (13) | 0.0088 (9) | 0.0252 (12) | −0.0036 (9) |
N1—C2 | 1.329 (3) | C9—H9A | 0.9700 |
N1—C9 | 1.456 (3) | C9—H9B | 0.9700 |
N1—C6 | 1.457 (3) | C10—H10A | 0.9600 |
C2—O2 | 1.230 (3) | C10—H10B | 0.9600 |
C2—C3 | 1.507 (3) | C10—H10C | 0.9600 |
C3—N4 | 1.469 (3) | C11—C12 | 1.503 (3) |
C3—C11 | 1.542 (3) | C11—H11A | 0.9700 |
C3—H3 | 0.9800 | C11—H11B | 0.9700 |
N4—C5 | 1.340 (3) | C12—C13 | 1.377 (4) |
N4—C10 | 1.457 (3) | C12—C17 | 1.386 (3) |
C5—O5 | 1.225 (3) | C13—C14 | 1.378 (4) |
C5—C6 | 1.499 (3) | C13—H13 | 0.9300 |
C6—C7 | 1.515 (3) | C14—C15 | 1.370 (5) |
C6—H6 | 0.9800 | C14—H14 | 0.9300 |
C7—C8 | 1.519 (4) | C15—C16 | 1.352 (4) |
C7—H7A | 0.9700 | C15—H15 | 0.9300 |
C7—H7B | 0.9700 | C16—C17 | 1.376 (4) |
C8—C9 | 1.508 (5) | C16—H16 | 0.9300 |
C8—H8A | 0.9700 | C17—H17 | 0.9300 |
C8—H8B | 0.9700 | ||
C2—N1—C9 | 123.5 (2) | N1—C9—C8 | 103.8 (2) |
C2—N1—C6 | 124.66 (18) | N1—C9—H9A | 111.0 |
C9—N1—C6 | 111.8 (2) | C8—C9—H9A | 111.0 |
O2—C2—N1 | 122.7 (2) | N1—C9—H9B | 111.0 |
O2—C2—C3 | 120.4 (2) | C8—C9—H9B | 111.0 |
N1—C2—C3 | 116.83 (19) | H9A—C9—H9B | 109.0 |
N4—C3—C2 | 113.05 (17) | N4—C10—H10A | 109.5 |
N4—C3—C11 | 113.11 (18) | N4—C10—H10B | 109.5 |
C2—C3—C11 | 111.32 (19) | H10A—C10—H10B | 109.5 |
N4—C3—H3 | 106.2 | N4—C10—H10C | 109.5 |
C2—C3—H3 | 106.2 | H10A—C10—H10C | 109.5 |
C11—C3—H3 | 106.2 | H10B—C10—H10C | 109.5 |
C5—N4—C10 | 119.4 (2) | C12—C11—C3 | 113.63 (18) |
C5—N4—C3 | 123.59 (18) | C12—C11—H11A | 108.8 |
C10—N4—C3 | 116.93 (19) | C3—C11—H11A | 108.8 |
O5—C5—N4 | 122.7 (2) | C12—C11—H11B | 108.8 |
O5—C5—C6 | 120.0 (2) | C3—C11—H11B | 108.8 |
N4—C5—C6 | 117.26 (19) | H11A—C11—H11B | 107.7 |
N1—C6—C5 | 113.16 (19) | C13—C12—C17 | 117.7 (2) |
N1—C6—C7 | 102.12 (18) | C13—C12—C11 | 121.0 (2) |
C5—C6—C7 | 115.6 (2) | C17—C12—C11 | 121.3 (2) |
N1—C6—H6 | 108.6 | C12—C13—C14 | 121.2 (3) |
C5—C6—H6 | 108.6 | C12—C13—H13 | 119.4 |
C7—C6—H6 | 108.6 | C14—C13—H13 | 119.4 |
C6—C7—C8 | 102.0 (2) | C15—C14—C13 | 119.9 (3) |
C6—C7—H7A | 111.4 | C15—C14—H14 | 120.0 |
C8—C7—H7A | 111.4 | C13—C14—H14 | 120.0 |
C6—C7—H7B | 111.4 | C16—C15—C14 | 119.7 (3) |
C8—C7—H7B | 111.4 | C16—C15—H15 | 120.2 |
H7A—C7—H7B | 109.2 | C14—C15—H15 | 120.2 |
C9—C8—C7 | 104.6 (2) | C15—C16—C17 | 120.8 (3) |
C9—C8—H8A | 110.8 | C15—C16—H16 | 119.6 |
C7—C8—H8A | 110.8 | C17—C16—H16 | 119.6 |
C9—C8—H8B | 110.8 | C16—C17—C12 | 120.7 (3) |
C7—C8—H8B | 110.8 | C16—C17—H17 | 119.7 |
H8A—C8—H8B | 108.9 | C12—C17—H17 | 119.7 |
C9—N1—C2—O2 | 5.0 (4) | N4—C5—C6—N1 | 25.5 (3) |
C6—N1—C2—O2 | −179.0 (2) | O5—C5—C6—C7 | −38.4 (3) |
C9—N1—C2—C3 | −175.4 (2) | N4—C5—C6—C7 | 142.7 (2) |
C6—N1—C2—C3 | 0.6 (3) | N1—C6—C7—C8 | −37.4 (3) |
O2—C2—C3—N4 | −154.3 (2) | C5—C6—C7—C8 | −160.6 (2) |
N1—C2—C3—N4 | 26.1 (3) | C6—C7—C8—C9 | 37.9 (3) |
O2—C2—C3—C11 | 77.1 (3) | C2—N1—C9—C8 | 175.5 (2) |
N1—C2—C3—C11 | −102.5 (2) | C6—N1—C9—C8 | −1.0 (3) |
C2—C3—N4—C5 | −27.5 (3) | C7—C8—C9—N1 | −23.1 (3) |
C11—C3—N4—C5 | 100.2 (3) | N4—C3—C11—C12 | −67.5 (3) |
C2—C3—N4—C10 | 155.7 (2) | C2—C3—C11—C12 | 61.0 (3) |
C11—C3—N4—C10 | −76.6 (3) | C3—C11—C12—C13 | −90.4 (3) |
C10—N4—C5—O5 | −1.0 (4) | C3—C11—C12—C17 | 87.7 (3) |
C3—N4—C5—O5 | −177.7 (2) | C17—C12—C13—C14 | −1.0 (4) |
C10—N4—C5—C6 | 177.9 (2) | C11—C12—C13—C14 | 177.2 (2) |
C3—N4—C5—C6 | 1.2 (3) | C12—C13—C14—C15 | 0.5 (5) |
C2—N1—C6—C5 | −27.0 (3) | C13—C14—C15—C16 | −0.2 (5) |
C9—N1—C6—C5 | 149.4 (2) | C14—C15—C16—C17 | 0.4 (5) |
C2—N1—C6—C7 | −151.9 (2) | C15—C16—C17—C12 | −1.0 (4) |
C9—N1—C6—C7 | 24.5 (3) | C13—C12—C17—C16 | 1.3 (4) |
O5—C5—C6—N1 | −155.6 (2) | C11—C12—C17—C16 | −176.9 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C3—H3···O5i | 0.98 | 2.44 | 3.386 (3) | 162 |
C8—H8A···O5ii | 0.97 | 2.59 | 3.491 (4) | 154 |
C15—H15···O2iii | 0.93 | 2.44 | 3.228 (4) | 143 |
Symmetry codes: (i) −x+1, y−1/2, −z+1/2; (ii) −x+3/2, −y+1, z−1/2; (iii) −x+2, y+1/2, −z+1/2. |