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The crystal structures of eight cyclodipeptides are determined, incorporating pipecolic acid or proline and phenylalanine or N-methyl phenylalanine. This set of structures allows the evaluation of the effects on molecular conformation and crystal packing of imino acid ring-size, relative configuration of the two amino acids, and N-methylation. In the non-methylated compounds, hydrogen-bonding interactions form one-dimensional motifs that dominate the packing arrangement. Three compounds have more than one symmetry-independent molecule in the asymmetric unit (Z′ > 1), indicative of a broad and shallow molecular energy minimum. Density functional theory calculations reveal the interplay between inter- and intramolecular factors in the crystals. Only for the N-methylated compounds do simulations of the molecules in the isolated state succeed to reproduce the observed crystallographic conformations. Puckering of the diketopiperazine ring and the deviation from planarity of the amide bonds are not reproduced in the remaining compounds. Cluster in vacuo calculations with a central cyclodipeptide molecule surrounded by hydrogen-bound molecules establish that hydrogen bonding is of major importance but that other intermolecular interactions must also contribute substantially to the crystal structure. More advanced periodic calculations, incorporating the crystallographic environment to the full extent, are necessary to correctly describe all the conformational features of these cyclodipeptide crystals.
Supporting information
| Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768110040243/so5040sup1.cif Contains datablocks 1a, 1a-room, 1b, 2a, 2b, 9a, 9b, 9b-room, 10a, 10b, 10b-room |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401asup2.hkl Contains datablock 1a |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401asup3.hkl Contains datablock 1a |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401a-roomsup4.hkl Contains datablock 1a-room |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50401bsup5.hkl Contains datablock 1b |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50402asup6.hkl Contains datablock 2a |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50402bsup7.hkl Contains datablock 2b |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50409asup8.hkl Contains datablock 9a |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50409bsup9.hkl Contains datablock 9b |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so50409b-roomsup10.hkl Contains datablock 9b-room |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so504010asup11.hkl Contains datablock 10a |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so504010bsup12.hkl Contains datablock 10b |
| Structure factor file (CIF format) https://doi.org/10.1107/S0108768110040243/so504010b-roomsup13.hkl Contains datablock 10b-room |
| Portable Document Format (PDF) file https://doi.org/10.1107/S0108768110040243/so5040sup14.pdf Extra tables and figures |
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).
Crystal data top
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 | |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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)* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Hydrogen-bond geometry (Å, º) top
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. |
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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)* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) | | |
Hydrogen-bond geometry (Å, º) top
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. |
Crystal data top
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 | |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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)* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 |
Hydrogen-bond geometry (Å, º) top
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. |
Crystal data top
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 | |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 |
Hydrogen-bond geometry (Å, º) top
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. |
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 |
Hydrogen-bond geometry (Å, º) top
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. |
Crystal data top
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 | |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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)* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 |
Hydrogen-bond geometry (Å, º) top
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. |
Crystal data top
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 | |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Hydrogen-bond geometry (Å, º) top
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. |
Crystal data top
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 | |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Hydrogen-bond geometry (Å, º) top
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. |
Crystal data top
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 | |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 |
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Hydrogen-bond geometry (Å, º) top
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. |
Crystal data top
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 |
Data collection top
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 top
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) |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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) | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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) |
Hydrogen-bond geometry (Å, º) top
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. |
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