Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520619011739/rm5017sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520619011739/rm5017form_IIsup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2052520619011739/rm5017form_IIIsup3.hkl | |
Portable Document Format (PDF) file https://doi.org/10.1107/S2052520619011739/rm5017sup4.pdf |
CCDC references: 1901918; 1937787
Data collection: CrysAlis PRO 1.171.38.46 (Rigaku OD, 2015) for form_II; CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018) for form_III. Cell refinement: CrysAlis PRO 1.171.38.46 (Rigaku OD, 2015) for form_II; CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018) for form_III. Data reduction: CrysAlis PRO 1.171.38.46 (Rigaku OD, 2015) for form_II; CrysAlis PRO 1.171.39.46 (Rigaku OD, 2018) for form_III. For both structures, program(s) used to solve structure: ShelXT (Sheldrick, 2015); program(s) used to refine structure: SHELXL (Sheldrick, 2015); molecular graphics: Olex2 (Dolomanov et al., 2009); software used to prepare material for publication: Olex2 (Dolomanov et al., 2009).
C15H17NO2·C6H6O2 | Dx = 1.248 Mg m−3 |
Mr = 353.40 | Cu Kα radiation, λ = 1.54184 Å |
Orthorhombic, P212121 | Cell parameters from 7942 reflections |
a = 7.2015 (1) Å | θ = 5.5–72.4° |
b = 12.2326 (1) Å | µ = 0.70 mm−1 |
c = 21.3487 (3) Å | T = 298 K |
V = 1880.67 (4) Å3 | Needle |
Z = 4 | 0.61 × 0.53 × 0.45 mm |
F(000) = 752 |
SuperNova, Dual, Cu at zero, AtlasS2 diffractometer | 3600 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 3470 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.029 |
Detector resolution: 5.2945 pixels mm-1 | θmax = 72.7°, θmin = 4.2° |
ω scans | h = −8→8 |
Absorption correction: gaussian CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −15→11 |
Tmin = 0.262, Tmax = 1.000 | l = −20→26 |
9920 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.046 | w = 1/[σ2(Fo2) + (0.0849P)2 + 0.0729P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.123 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.15 e Å−3 |
3600 reflections | Δρmin = −0.21 e Å−3 |
249 parameters | Absolute structure: Flack x determined using 1335 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
0 restraints | Absolute structure parameter: −0.04 (11) |
Primary atom site location: dual |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O3 | 0.6326 (2) | 0.72316 (18) | 0.17564 (9) | 0.0601 (5) | |
O2 | 0.7104 (3) | 0.64128 (14) | 0.28586 (8) | 0.0603 (5) | |
O4 | −0.0882 (2) | 0.72363 (19) | 0.08696 (9) | 0.0664 (5) | |
O1 | 1.1265 (4) | 0.94932 (16) | 0.33596 (11) | 0.0835 (7) | |
N1 | 0.7197 (3) | 0.50144 (18) | 0.35358 (10) | 0.0551 (5) | |
C19 | 0.0870 (3) | 0.72433 (18) | 0.11141 (10) | 0.0473 (5) | |
C3 | 1.1675 (3) | 0.75966 (19) | 0.36562 (9) | 0.0488 (5) | |
H3 | 1.068493 | 0.737459 | 0.340699 | 0.059* | |
C18 | 0.1219 (3) | 0.71991 (18) | 0.17521 (10) | 0.0455 (5) | |
H18 | 0.023349 | 0.716685 | 0.203314 | 0.055* | |
C2 | 1.2646 (3) | 0.68147 (19) | 0.40241 (9) | 0.0451 (5) | |
C16 | 0.4513 (3) | 0.72339 (18) | 0.15620 (10) | 0.0445 (4) | |
C17 | 0.3025 (3) | 0.72026 (17) | 0.19730 (10) | 0.0448 (4) | |
H17 | 0.324234 | 0.718367 | 0.240228 | 0.054* | |
C13 | 0.6531 (3) | 0.55069 (18) | 0.30278 (11) | 0.0491 (5) | |
C7 | 1.4165 (3) | 0.7172 (2) | 0.44006 (10) | 0.0518 (5) | |
C1 | 1.2131 (3) | 0.56926 (18) | 0.40433 (10) | 0.0474 (5) | |
C11 | 1.0576 (3) | 0.52604 (19) | 0.36370 (11) | 0.0509 (5) | |
H11A | 1.074479 | 0.448074 | 0.357661 | 0.061* | |
H11B | 1.063835 | 0.560835 | 0.322922 | 0.061* | |
C8 | 1.5043 (3) | 0.6424 (2) | 0.48072 (12) | 0.0605 (6) | |
H8 | 1.603093 | 0.665713 | 0.505400 | 0.073* | |
C4 | 1.2186 (4) | 0.8671 (2) | 0.36663 (11) | 0.0601 (6) | |
C14 | 0.5035 (4) | 0.4901 (2) | 0.26812 (13) | 0.0612 (6) | |
H14A | 0.384711 | 0.507932 | 0.285762 | 0.092* | |
H14B | 0.524527 | 0.412813 | 0.271715 | 0.092* | |
H14C | 0.505713 | 0.510689 | 0.224740 | 0.092* | |
C21 | 0.4159 (3) | 0.7294 (2) | 0.09249 (11) | 0.0541 (5) | |
H21 | 0.514323 | 0.732485 | 0.064350 | 0.065* | |
C20 | 0.2360 (3) | 0.7310 (2) | 0.07048 (11) | 0.0566 (6) | |
H20 | 0.214368 | 0.736622 | 0.027659 | 0.068* | |
C10 | 1.3019 (4) | 0.5000 (2) | 0.44545 (12) | 0.0594 (6) | |
H10 | 1.264949 | 0.427233 | 0.447462 | 0.071* | |
C6 | 1.4698 (4) | 0.8287 (3) | 0.43667 (13) | 0.0647 (7) | |
H6 | 1.572654 | 0.852234 | 0.459293 | 0.078* | |
C12 | 0.8675 (3) | 0.5464 (2) | 0.39204 (11) | 0.0541 (5) | |
H12A | 0.862390 | 0.513608 | 0.433371 | 0.065* | |
H12B | 0.848721 | 0.624505 | 0.396765 | 0.065* | |
C9 | 1.4465 (4) | 0.5360 (3) | 0.48441 (14) | 0.0675 (7) | |
H9 | 1.502402 | 0.488047 | 0.512465 | 0.081* | |
C5 | 1.3747 (4) | 0.9019 (2) | 0.40135 (14) | 0.0710 (8) | |
H5 | 1.412195 | 0.974598 | 0.399986 | 0.085* | |
C15 | 0.9477 (6) | 0.9246 (3) | 0.3117 (2) | 0.0942 (12) | |
H15A | 0.958256 | 0.868388 | 0.280506 | 0.141* | |
H15B | 0.895032 | 0.989017 | 0.293151 | 0.141* | |
H15C | 0.868846 | 0.899623 | 0.345022 | 0.141* | |
H1 | 0.674 (4) | 0.437 (3) | 0.3605 (13) | 0.062 (8)* | |
H4 | −0.158 (4) | 0.732 (3) | 0.1187 (17) | 0.075 (10)* | |
H3A | 0.647 (5) | 0.701 (3) | 0.2125 (18) | 0.079 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O3 | 0.0365 (7) | 0.0861 (12) | 0.0577 (10) | 0.0024 (8) | −0.0015 (7) | 0.0149 (9) |
O2 | 0.0618 (10) | 0.0568 (9) | 0.0625 (10) | −0.0068 (8) | −0.0157 (8) | 0.0094 (8) |
O4 | 0.0422 (8) | 0.1001 (14) | 0.0570 (10) | −0.0004 (9) | −0.0080 (8) | 0.0029 (10) |
O1 | 0.1123 (19) | 0.0583 (11) | 0.0799 (13) | −0.0007 (12) | −0.0021 (14) | 0.0182 (10) |
N1 | 0.0487 (10) | 0.0594 (11) | 0.0571 (11) | −0.0099 (9) | −0.0090 (9) | 0.0093 (9) |
C19 | 0.0412 (10) | 0.0526 (11) | 0.0482 (11) | 0.0016 (9) | −0.0045 (9) | −0.0007 (9) |
C3 | 0.0513 (11) | 0.0562 (11) | 0.0388 (9) | −0.0024 (9) | −0.0015 (9) | −0.0013 (8) |
C18 | 0.0413 (9) | 0.0499 (10) | 0.0454 (10) | 0.0023 (9) | 0.0064 (8) | 0.0022 (9) |
C2 | 0.0401 (10) | 0.0570 (11) | 0.0381 (9) | 0.0006 (8) | 0.0023 (8) | −0.0047 (9) |
C16 | 0.0365 (9) | 0.0501 (10) | 0.0471 (11) | 0.0018 (8) | −0.0019 (8) | 0.0047 (9) |
C17 | 0.0444 (10) | 0.0511 (10) | 0.0390 (9) | 0.0037 (9) | 0.0014 (8) | 0.0028 (9) |
C13 | 0.0410 (10) | 0.0540 (11) | 0.0523 (11) | 0.0006 (9) | −0.0045 (9) | −0.0011 (9) |
C7 | 0.0390 (10) | 0.0737 (14) | 0.0426 (10) | −0.0045 (10) | 0.0023 (9) | −0.0119 (10) |
C1 | 0.0417 (10) | 0.0560 (11) | 0.0444 (10) | 0.0053 (9) | −0.0019 (9) | −0.0047 (9) |
C11 | 0.0500 (12) | 0.0519 (11) | 0.0508 (12) | 0.0006 (9) | −0.0065 (10) | −0.0043 (9) |
C8 | 0.0419 (10) | 0.0895 (17) | 0.0500 (12) | 0.0035 (12) | −0.0084 (10) | −0.0113 (12) |
C4 | 0.0751 (16) | 0.0564 (12) | 0.0488 (12) | −0.0057 (11) | 0.0102 (12) | 0.0057 (10) |
C14 | 0.0516 (12) | 0.0654 (13) | 0.0667 (15) | −0.0015 (11) | −0.0163 (12) | −0.0032 (12) |
C21 | 0.0437 (10) | 0.0743 (14) | 0.0443 (11) | 0.0005 (10) | 0.0089 (9) | 0.0027 (11) |
C20 | 0.0530 (13) | 0.0778 (15) | 0.0391 (10) | 0.0029 (11) | −0.0016 (9) | −0.0005 (11) |
C10 | 0.0562 (13) | 0.0591 (12) | 0.0630 (14) | 0.0074 (11) | −0.0080 (12) | 0.0006 (11) |
C6 | 0.0543 (13) | 0.0817 (17) | 0.0580 (14) | −0.0199 (13) | 0.0053 (11) | −0.0148 (13) |
C12 | 0.0485 (11) | 0.0676 (13) | 0.0463 (11) | −0.0059 (10) | −0.0057 (10) | 0.0021 (10) |
C9 | 0.0604 (14) | 0.0833 (17) | 0.0586 (14) | 0.0181 (13) | −0.0164 (12) | 0.0027 (13) |
C5 | 0.0842 (19) | 0.0667 (15) | 0.0620 (15) | −0.0286 (14) | 0.0137 (15) | −0.0042 (12) |
C15 | 0.125 (3) | 0.0640 (16) | 0.094 (2) | 0.0183 (19) | −0.033 (2) | 0.0065 (16) |
O3—C16 | 1.370 (2) | C1—C11 | 1.512 (3) |
O3—H3A | 0.84 (4) | C1—C10 | 1.377 (3) |
O2—C13 | 1.236 (3) | C11—H11A | 0.9700 |
O4—C19 | 1.365 (3) | C11—H11B | 0.9700 |
O4—H4 | 0.85 (4) | C11—C12 | 1.517 (3) |
O1—C4 | 1.371 (3) | C8—H8 | 0.9300 |
O1—C15 | 1.421 (4) | C8—C9 | 1.369 (4) |
N1—C13 | 1.330 (3) | C4—C5 | 1.412 (4) |
N1—C12 | 1.453 (3) | C14—H14A | 0.9600 |
N1—H1 | 0.87 (3) | C14—H14B | 0.9600 |
C19—C18 | 1.386 (3) | C14—H14C | 0.9600 |
C19—C20 | 1.387 (3) | C21—H21 | 0.9300 |
C3—H3 | 0.9300 | C21—C20 | 1.378 (3) |
C3—C2 | 1.421 (3) | C20—H20 | 0.9300 |
C3—C4 | 1.366 (3) | C10—H10 | 0.9300 |
C18—H18 | 0.9300 | C10—C9 | 1.403 (4) |
C18—C17 | 1.384 (3) | C6—H6 | 0.9300 |
C2—C7 | 1.427 (3) | C6—C5 | 1.356 (4) |
C2—C1 | 1.422 (3) | C12—H12A | 0.9700 |
C16—C17 | 1.386 (3) | C12—H12B | 0.9700 |
C16—C21 | 1.386 (3) | C9—H9 | 0.9300 |
C17—H17 | 0.9300 | C5—H5 | 0.9300 |
C13—C14 | 1.503 (3) | C15—H15A | 0.9600 |
C7—C8 | 1.411 (4) | C15—H15B | 0.9600 |
C7—C6 | 1.418 (4) | C15—H15C | 0.9600 |
C16—O3—H3A | 114 (2) | C9—C8—H8 | 119.5 |
C19—O4—H4 | 104 (2) | O1—C4—C5 | 114.5 (2) |
C4—O1—C15 | 117.2 (2) | C3—C4—O1 | 124.6 (3) |
C13—N1—C12 | 123.6 (2) | C3—C4—C5 | 120.8 (3) |
C13—N1—H1 | 115 (2) | C13—C14—H14A | 109.5 |
C12—N1—H1 | 122 (2) | C13—C14—H14B | 109.5 |
O4—C19—C18 | 122.9 (2) | C13—C14—H14C | 109.5 |
O4—C19—C20 | 118.4 (2) | H14A—C14—H14B | 109.5 |
C18—C19—C20 | 118.8 (2) | H14A—C14—H14C | 109.5 |
C2—C3—H3 | 119.8 | H14B—C14—H14C | 109.5 |
C4—C3—H3 | 119.8 | C16—C21—H21 | 119.7 |
C4—C3—C2 | 120.4 (2) | C20—C21—C16 | 120.6 (2) |
C19—C18—H18 | 119.8 | C20—C21—H21 | 119.7 |
C17—C18—C19 | 120.35 (19) | C19—C20—H20 | 119.6 |
C17—C18—H18 | 119.8 | C21—C20—C19 | 120.8 (2) |
C3—C2—C7 | 118.8 (2) | C21—C20—H20 | 119.6 |
C3—C2—C1 | 122.5 (2) | C1—C10—H10 | 119.0 |
C1—C2—C7 | 118.6 (2) | C1—C10—C9 | 121.9 (2) |
O3—C16—C17 | 123.0 (2) | C9—C10—H10 | 119.0 |
O3—C16—C21 | 118.22 (19) | C7—C6—H6 | 119.1 |
C17—C16—C21 | 118.72 (19) | C5—C6—C7 | 121.8 (2) |
C18—C17—C16 | 120.75 (18) | C5—C6—H6 | 119.1 |
C18—C17—H17 | 119.6 | N1—C12—C11 | 111.9 (2) |
C16—C17—H17 | 119.6 | N1—C12—H12A | 109.2 |
O2—C13—N1 | 121.6 (2) | N1—C12—H12B | 109.2 |
O2—C13—C14 | 122.5 (2) | C11—C12—H12A | 109.2 |
N1—C13—C14 | 115.9 (2) | C11—C12—H12B | 109.2 |
C8—C7—C2 | 119.4 (2) | H12A—C12—H12B | 107.9 |
C8—C7—C6 | 122.3 (2) | C8—C9—C10 | 119.3 (2) |
C6—C7—C2 | 118.3 (2) | C8—C9—H9 | 120.3 |
C2—C1—C11 | 120.91 (19) | C10—C9—H9 | 120.3 |
C10—C1—C2 | 119.4 (2) | C4—C5—H5 | 120.2 |
C10—C1—C11 | 119.6 (2) | C6—C5—C4 | 119.7 (2) |
C1—C11—H11A | 109.1 | C6—C5—H5 | 120.2 |
C1—C11—H11B | 109.1 | O1—C15—H15A | 109.5 |
C1—C11—C12 | 112.45 (19) | O1—C15—H15B | 109.5 |
H11A—C11—H11B | 107.8 | O1—C15—H15C | 109.5 |
C12—C11—H11A | 109.1 | H15A—C15—H15B | 109.5 |
C12—C11—H11B | 109.1 | H15A—C15—H15C | 109.5 |
C7—C8—H8 | 119.5 | H15B—C15—H15C | 109.5 |
C9—C8—C7 | 121.1 (2) |
C15H17NO2·C6H6O2· | F(000) = 752 |
Mr = 353.40 | Dx = 1.245 Mg m−3 |
Monoclinic, P21 | Cu Kα radiation, λ = 1.54184 Å |
a = 7.3330 (1) Å | Cell parameters from 12027 reflections |
b = 29.3095 (4) Å | θ = 3.0–72.3° |
c = 8.8046 (1) Å | µ = 0.70 mm−1 |
β = 94.748 (1)° | T = 293 K |
V = 1885.85 (4) Å3 | Needle, colourless |
Z = 4 | 0.52 × 0.16 × 0.12 mm |
SuperNova, Dual, Cu at home/near, AtlasS2 diffractometer | 7276 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 6726 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.031 |
Detector resolution: 5.2945 pixels mm-1 | θmax = 72.8°, θmin = 3.0° |
ω scans | h = −8→7 |
Absorption correction: gaussian CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | k = −36→36 |
Tmin = 0.667, Tmax = 1.000 | l = −10→10 |
20956 measured reflections |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.049 | w = 1/[σ2(Fo2) + (0.0818P)2 + 0.0942P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.133 | (Δ/σ)max = 0.001 |
S = 1.06 | Δρmax = 0.14 e Å−3 |
7276 reflections | Δρmin = −0.23 e Å−3 |
497 parameters | Absolute structure: Flack x determined using 2905 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
1 restraint | Absolute structure parameter: −0.13 (7) |
Primary atom site location: dual |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
x | y | z | Uiso*/Ueq | ||
O6 | 1.5047 (3) | 0.71165 (9) | 1.3203 (3) | 0.0674 (6) | |
O2 | 1.0691 (4) | 0.34859 (9) | 0.5717 (2) | 0.0799 (7) | |
O4 | 0.6484 (3) | 0.65400 (10) | 0.8765 (3) | 0.0760 (6) | |
O7 | 0.9640 (3) | 0.30435 (10) | 0.3189 (3) | 0.0743 (6) | |
O8 | 0.2316 (3) | 0.29514 (10) | 0.1162 (3) | 0.0750 (7) | |
O5 | 0.7733 (3) | 0.68286 (12) | 1.1446 (3) | 0.0846 (8) | |
O1 | 0.7118 (7) | 0.45650 (12) | 0.3444 (4) | 0.1168 (12) | |
N2 | 1.0625 (4) | 0.33104 (9) | 0.8181 (3) | 0.0610 (6) | |
N1 | 0.5312 (4) | 0.67609 (10) | 0.6465 (3) | 0.0666 (6) | |
C34 | 1.3247 (4) | 0.70460 (9) | 1.2678 (3) | 0.0512 (6) | |
C13 | 1.1485 (4) | 0.33506 (10) | 0.6928 (3) | 0.0587 (7) | |
C31 | 0.9572 (4) | 0.69011 (11) | 1.1819 (3) | 0.0571 (6) | |
C40 | 0.4119 (4) | 0.29761 (10) | 0.1739 (3) | 0.0547 (6) | |
C41 | 0.5396 (4) | 0.27323 (10) | 0.1014 (3) | 0.0574 (6) | |
H41 | 0.502195 | 0.254923 | 0.018324 | 0.069* | |
C38 | 0.6524 (4) | 0.32671 (11) | 0.3500 (3) | 0.0572 (6) | |
H38 | 0.689941 | 0.344485 | 0.434319 | 0.069* | |
C33 | 1.1909 (4) | 0.72616 (10) | 1.3438 (3) | 0.0570 (6) | |
H33 | 1.224473 | 0.745784 | 1.424261 | 0.068* | |
C39 | 0.4679 (4) | 0.32449 (11) | 0.2988 (3) | 0.0583 (6) | |
H39 | 0.382268 | 0.341020 | 0.348373 | 0.070* | |
C1 | 0.6750 (4) | 0.41301 (11) | 0.8778 (4) | 0.0633 (7) | |
C37 | 0.7799 (4) | 0.30247 (10) | 0.2753 (3) | 0.0524 (6) | |
C36 | 1.0883 (4) | 0.66899 (12) | 1.1045 (3) | 0.0619 (7) | |
H36 | 1.053762 | 0.649682 | 1.023336 | 0.074* | |
C28 | 0.6691 (4) | 0.67249 (11) | 0.7532 (3) | 0.0620 (7) | |
C11 | 0.8633 (5) | 0.39295 (11) | 0.8936 (3) | 0.0638 (7) | |
H11A | 0.905654 | 0.391835 | 1.000866 | 0.077* | |
H11B | 0.945148 | 0.412864 | 0.843371 | 0.077* | |
C42 | 0.7227 (4) | 0.27576 (10) | 0.1512 (3) | 0.0569 (6) | |
H42 | 0.808066 | 0.259391 | 0.100813 | 0.068* | |
C2 | 0.6021 (4) | 0.43238 (9) | 0.7382 (4) | 0.0642 (7) | |
C27 | 0.3535 (4) | 0.65668 (11) | 0.6623 (3) | 0.0618 (7) | |
H27A | 0.260785 | 0.675775 | 0.609269 | 0.074* | |
H27B | 0.330918 | 0.656096 | 0.769235 | 0.074* | |
C32 | 1.0090 (4) | 0.71878 (11) | 1.3011 (3) | 0.0592 (7) | |
H32 | 0.920264 | 0.733301 | 1.353207 | 0.071* | |
C12 | 0.8743 (4) | 0.34523 (11) | 0.8268 (4) | 0.0619 (7) | |
H12A | 0.813230 | 0.323855 | 0.889758 | 0.074* | |
H12B | 0.811179 | 0.344780 | 0.725564 | 0.074* | |
O3 | 0.3279 (11) | 0.54997 (18) | 1.1596 (6) | 0.161 (3) | |
C35 | 1.2729 (4) | 0.67640 (11) | 1.1470 (3) | 0.0585 (6) | |
H35 | 1.361440 | 0.662250 | 1.093621 | 0.070* | |
C3 | 0.7016 (5) | 0.43392 (10) | 0.6080 (4) | 0.0694 (8) | |
H3 | 0.819107 | 0.421822 | 0.611995 | 0.083* | |
C26 | 0.3380 (5) | 0.60850 (12) | 0.5983 (4) | 0.0697 (8) | |
H26A | 0.353780 | 0.609339 | 0.490039 | 0.084* | |
H26B | 0.435139 | 0.589856 | 0.647200 | 0.084* | |
C7 | 0.4216 (5) | 0.45099 (11) | 0.7306 (6) | 0.0858 (12) | |
C18 | 0.2502 (6) | 0.56915 (11) | 0.8934 (5) | 0.0786 (10) | |
H18 | 0.366447 | 0.580781 | 0.882898 | 0.094* | |
C19 | 0.2079 (10) | 0.55178 (15) | 1.0326 (8) | 0.119 (2) | |
C5 | 0.4444 (9) | 0.47123 (14) | 0.4709 (8) | 0.1113 (19) | |
H5 | 0.391022 | 0.483413 | 0.380356 | 0.134* | |
C8 | 0.3232 (6) | 0.44940 (15) | 0.8619 (8) | 0.1022 (17) | |
H8 | 0.206871 | 0.462214 | 0.858528 | 0.123* | |
C29 | 0.8492 (5) | 0.69121 (16) | 0.7160 (5) | 0.0872 (11) | |
H29A | 0.904322 | 0.707624 | 0.802303 | 0.131* | |
H29B | 0.831158 | 0.711459 | 0.630371 | 0.131* | |
H29C | 0.927919 | 0.666599 | 0.691378 | 0.131* | |
C16 | 0.1559 (5) | 0.58701 (12) | 0.6225 (5) | 0.0808 (11) | |
C4 | 0.6261 (7) | 0.45311 (11) | 0.4757 (5) | 0.0857 (12) | |
C17 | 0.1177 (5) | 0.56930 (11) | 0.7673 (6) | 0.0817 (11) | |
C14 | 1.3475 (5) | 0.32275 (13) | 0.7044 (4) | 0.0743 (9) | |
H14A | 1.364039 | 0.294859 | 0.650013 | 0.111* | |
H14B | 1.390303 | 0.318797 | 0.809548 | 0.111* | |
H14C | 1.415718 | 0.346723 | 0.660918 | 0.111* | |
C6 | 0.3512 (7) | 0.47090 (15) | 0.5935 (8) | 0.1066 (17) | |
H6 | 0.235774 | 0.484252 | 0.588341 | 0.128* | |
C9 | 0.3942 (7) | 0.42972 (17) | 0.9920 (8) | 0.1066 (16) | |
H9 | 0.325511 | 0.428051 | 1.076030 | 0.128* | |
C10 | 0.5689 (6) | 0.41206 (14) | 1.0000 (5) | 0.0849 (10) | |
H10 | 0.616893 | 0.399048 | 1.090991 | 0.102* | |
C24 | −0.1521 (13) | 0.5676 (3) | 0.5239 (16) | 0.195 (7) | |
H24 | −0.242386 | 0.567468 | 0.443257 | 0.234* | |
C22 | −0.0582 (7) | 0.55074 (14) | 0.7833 (10) | 0.126 (3) | |
C25 | 0.0230 (8) | 0.58584 (18) | 0.5026 (8) | 0.126 (2) | |
H25 | 0.048102 | 0.597021 | 0.407704 | 0.152* | |
C15 | 0.8954 (10) | 0.4438 (2) | 0.3465 (6) | 0.1168 (19) | |
H15A | 0.938922 | 0.449556 | 0.248418 | 0.175* | |
H15B | 0.907319 | 0.411883 | 0.369881 | 0.175* | |
H15C | 0.966316 | 0.461186 | 0.422604 | 0.175* | |
C20 | 0.0310 (18) | 0.5343 (2) | 1.0421 (16) | 0.186 (6) | |
H20 | 0.001775 | 0.522632 | 1.135300 | 0.223* | |
C21 | −0.0957 (13) | 0.5332 (2) | 0.9278 (19) | 0.184 (6) | |
H21 | −0.210197 | 0.521003 | 0.941532 | 0.221* | |
C23 | −0.1875 (12) | 0.5510 (3) | 0.6546 (19) | 0.201 (8) | |
H23 | −0.302862 | 0.538703 | 0.664362 | 0.241* | |
C30 | 0.5085 (16) | 0.5581 (3) | 1.1400 (9) | 0.170 (4) | |
H30A | 0.546256 | 0.539286 | 1.059089 | 0.255* | |
H30B | 0.581640 | 0.551213 | 1.232595 | 0.255* | |
H30C | 0.524207 | 0.589672 | 1.114445 | 0.255* | |
H2 | 1.117 (5) | 0.3233 (13) | 0.899 (5) | 0.070 (10)* | |
H5A | 0.755 (6) | 0.6733 (16) | 1.050 (6) | 0.094 (14)* | |
H8A | 0.149 (6) | 0.3048 (16) | 0.187 (5) | 0.087 (12)* | |
H6A | 1.584 (6) | 0.7018 (15) | 1.261 (5) | 0.080 (12)* | |
H7 | 0.996 (7) | 0.3220 (18) | 0.411 (6) | 0.105 (14)* | |
H1 | 0.545 (5) | 0.6888 (14) | 0.565 (5) | 0.074 (11)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O6 | 0.0471 (11) | 0.0896 (15) | 0.0658 (12) | −0.0090 (10) | 0.0052 (9) | −0.0088 (11) |
O2 | 0.0872 (17) | 0.0967 (17) | 0.0531 (11) | 0.0042 (14) | −0.0109 (11) | 0.0057 (11) |
O4 | 0.0684 (15) | 0.0968 (16) | 0.0611 (12) | −0.0069 (12) | −0.0045 (10) | 0.0083 (11) |
O7 | 0.0419 (11) | 0.1112 (18) | 0.0687 (13) | 0.0071 (11) | −0.0014 (9) | −0.0137 (13) |
O8 | 0.0435 (11) | 0.124 (2) | 0.0568 (11) | −0.0011 (12) | −0.0016 (9) | 0.0031 (12) |
O5 | 0.0415 (11) | 0.145 (2) | 0.0671 (13) | 0.0008 (13) | 0.0040 (9) | −0.0159 (14) |
O1 | 0.169 (4) | 0.095 (2) | 0.0786 (19) | −0.005 (2) | −0.031 (2) | 0.0194 (15) |
N2 | 0.0579 (14) | 0.0710 (14) | 0.0520 (12) | 0.0054 (11) | −0.0074 (11) | 0.0092 (10) |
N1 | 0.0646 (16) | 0.0801 (16) | 0.0549 (13) | −0.0025 (13) | 0.0041 (11) | 0.0095 (12) |
C34 | 0.0455 (14) | 0.0583 (13) | 0.0499 (13) | −0.0010 (10) | 0.0048 (10) | 0.0069 (10) |
C13 | 0.0616 (17) | 0.0597 (14) | 0.0529 (14) | −0.0026 (12) | −0.0071 (12) | −0.0043 (11) |
C31 | 0.0439 (14) | 0.0773 (17) | 0.0502 (13) | 0.0037 (12) | 0.0047 (11) | 0.0032 (12) |
C40 | 0.0428 (14) | 0.0751 (16) | 0.0458 (12) | −0.0029 (12) | 0.0016 (10) | 0.0115 (11) |
C41 | 0.0549 (16) | 0.0668 (15) | 0.0502 (13) | −0.0025 (12) | 0.0032 (11) | −0.0051 (11) |
C38 | 0.0507 (15) | 0.0715 (16) | 0.0490 (13) | 0.0018 (12) | 0.0023 (10) | −0.0052 (11) |
C33 | 0.0600 (16) | 0.0573 (14) | 0.0533 (14) | 0.0040 (12) | 0.0025 (12) | −0.0044 (11) |
C39 | 0.0468 (15) | 0.0773 (17) | 0.0513 (13) | 0.0100 (13) | 0.0077 (11) | 0.0019 (12) |
C1 | 0.0574 (17) | 0.0601 (15) | 0.0718 (17) | −0.0090 (13) | 0.0027 (14) | −0.0077 (13) |
C37 | 0.0418 (13) | 0.0666 (14) | 0.0483 (12) | 0.0031 (11) | 0.0021 (10) | 0.0034 (11) |
C36 | 0.0504 (15) | 0.0789 (18) | 0.0560 (14) | 0.0012 (13) | 0.0025 (11) | −0.0119 (13) |
C28 | 0.0586 (17) | 0.0645 (15) | 0.0631 (16) | −0.0025 (13) | 0.0073 (12) | −0.0035 (13) |
C11 | 0.0583 (17) | 0.0771 (18) | 0.0548 (14) | −0.0053 (14) | −0.0036 (12) | −0.0007 (13) |
C42 | 0.0506 (15) | 0.0659 (15) | 0.0542 (13) | 0.0086 (12) | 0.0048 (11) | −0.0043 (12) |
C2 | 0.0574 (17) | 0.0458 (13) | 0.087 (2) | −0.0072 (12) | −0.0054 (15) | −0.0078 (13) |
C27 | 0.0561 (17) | 0.0705 (16) | 0.0578 (15) | 0.0023 (13) | −0.0008 (12) | 0.0055 (12) |
C32 | 0.0528 (15) | 0.0686 (16) | 0.0569 (14) | 0.0145 (13) | 0.0097 (12) | −0.0007 (12) |
C12 | 0.0537 (16) | 0.0670 (16) | 0.0639 (16) | −0.0035 (13) | −0.0016 (12) | 0.0109 (12) |
O3 | 0.249 (7) | 0.137 (3) | 0.105 (3) | 0.069 (4) | 0.070 (4) | 0.056 (3) |
C35 | 0.0468 (14) | 0.0758 (17) | 0.0538 (14) | 0.0062 (13) | 0.0085 (11) | −0.0080 (12) |
C3 | 0.075 (2) | 0.0510 (14) | 0.0778 (19) | −0.0056 (13) | −0.0202 (16) | 0.0012 (13) |
C26 | 0.072 (2) | 0.0742 (18) | 0.0622 (16) | 0.0108 (16) | 0.0026 (15) | −0.0035 (14) |
C7 | 0.065 (2) | 0.0455 (14) | 0.142 (4) | −0.0020 (13) | −0.019 (2) | −0.0159 (18) |
C18 | 0.079 (2) | 0.0557 (15) | 0.105 (3) | 0.0082 (15) | 0.032 (2) | 0.0095 (16) |
C19 | 0.160 (5) | 0.066 (2) | 0.142 (5) | 0.024 (3) | 0.080 (4) | 0.020 (3) |
C5 | 0.127 (4) | 0.066 (2) | 0.128 (4) | 0.009 (2) | −0.068 (4) | 0.007 (2) |
C8 | 0.062 (2) | 0.070 (2) | 0.178 (5) | −0.0069 (17) | 0.026 (3) | −0.036 (3) |
C29 | 0.068 (2) | 0.094 (2) | 0.102 (3) | −0.0191 (19) | 0.0168 (19) | −0.006 (2) |
C16 | 0.068 (2) | 0.0599 (16) | 0.110 (3) | 0.0075 (15) | −0.0156 (19) | −0.0276 (18) |
C4 | 0.117 (3) | 0.0578 (17) | 0.076 (2) | −0.0068 (18) | −0.030 (2) | 0.0066 (15) |
C17 | 0.065 (2) | 0.0469 (14) | 0.136 (3) | 0.0019 (14) | 0.021 (2) | −0.0148 (18) |
C14 | 0.066 (2) | 0.079 (2) | 0.078 (2) | 0.0093 (16) | 0.0033 (16) | −0.0064 (16) |
C6 | 0.088 (3) | 0.066 (2) | 0.157 (5) | 0.012 (2) | −0.041 (3) | −0.009 (3) |
C9 | 0.088 (3) | 0.090 (3) | 0.148 (5) | −0.011 (2) | 0.044 (3) | −0.023 (3) |
C10 | 0.079 (2) | 0.086 (2) | 0.092 (2) | −0.0103 (19) | 0.022 (2) | −0.016 (2) |
C24 | 0.107 (7) | 0.130 (7) | 0.327 (15) | 0.019 (5) | −0.103 (9) | −0.114 (9) |
C22 | 0.067 (3) | 0.0529 (18) | 0.263 (8) | −0.0038 (18) | 0.038 (4) | −0.032 (3) |
C25 | 0.107 (4) | 0.098 (3) | 0.163 (5) | 0.014 (3) | −0.055 (4) | −0.055 (3) |
C15 | 0.161 (6) | 0.113 (4) | 0.077 (3) | −0.037 (4) | 0.011 (3) | 0.020 (2) |
C20 | 0.222 (10) | 0.072 (3) | 0.294 (13) | 0.025 (5) | 0.202 (10) | 0.042 (6) |
C21 | 0.128 (6) | 0.065 (3) | 0.379 (19) | −0.008 (4) | 0.147 (9) | −0.007 (6) |
C23 | 0.069 (4) | 0.088 (4) | 0.44 (2) | −0.002 (3) | −0.003 (9) | −0.108 (9) |
C30 | 0.224 (10) | 0.181 (8) | 0.103 (5) | 0.045 (7) | 0.003 (5) | 0.054 (5) |
O6—C34 | 1.378 (3) | C12—H12A | 0.9700 |
O6—H6A | 0.86 (5) | C12—H12B | 0.9700 |
O2—C13 | 1.237 (4) | O3—C19 | 1.366 (9) |
O4—C28 | 1.234 (4) | O3—C30 | 1.371 (11) |
O7—C37 | 1.374 (3) | C35—H35 | 0.9300 |
O7—H7 | 0.97 (5) | C3—H3 | 0.9300 |
O8—C40 | 1.379 (3) | C3—C4 | 1.369 (5) |
O8—H8A | 0.95 (5) | C26—H26A | 0.9700 |
O5—C31 | 1.378 (4) | C26—H26B | 0.9700 |
O5—H5A | 0.88 (5) | C26—C16 | 1.507 (6) |
O1—C4 | 1.364 (6) | C7—C8 | 1.414 (8) |
O1—C15 | 1.396 (7) | C7—C6 | 1.401 (8) |
N2—C13 | 1.321 (4) | C18—H18 | 0.9300 |
N2—C12 | 1.450 (4) | C18—C19 | 1.385 (7) |
N2—H2 | 0.82 (4) | C18—C17 | 1.413 (6) |
N1—C28 | 1.327 (4) | C19—C20 | 1.404 (13) |
N1—C27 | 1.439 (4) | C5—H5 | 0.9300 |
N1—H1 | 0.82 (4) | C5—C4 | 1.432 (7) |
C34—C33 | 1.385 (4) | C5—C6 | 1.324 (8) |
C34—C35 | 1.375 (4) | C8—H8 | 0.9300 |
C13—C14 | 1.499 (4) | C8—C9 | 1.348 (8) |
C31—C36 | 1.372 (4) | C29—H29A | 0.9600 |
C31—C32 | 1.373 (4) | C29—H29B | 0.9600 |
C40—C41 | 1.376 (4) | C29—H29C | 0.9600 |
C40—C39 | 1.387 (4) | C16—C17 | 1.426 (7) |
C41—H41 | 0.9300 | C16—C25 | 1.376 (6) |
C41—C42 | 1.379 (4) | C17—C22 | 1.418 (6) |
C38—H38 | 0.9300 | C14—H14A | 0.9600 |
C38—C39 | 1.391 (4) | C14—H14B | 0.9600 |
C38—C37 | 1.383 (4) | C14—H14C | 0.9600 |
C33—H33 | 0.9300 | C6—H6 | 0.9300 |
C33—C32 | 1.372 (4) | C9—H9 | 0.9300 |
C39—H39 | 0.9300 | C9—C10 | 1.378 (7) |
C1—C11 | 1.496 (5) | C10—H10 | 0.9300 |
C1—C2 | 1.418 (5) | C24—H24 | 0.9300 |
C1—C10 | 1.379 (5) | C24—C25 | 1.418 (13) |
C37—C42 | 1.381 (4) | C24—C23 | 1.295 (18) |
C36—H36 | 0.9300 | C22—C21 | 1.420 (16) |
C36—C35 | 1.391 (4) | C22—C23 | 1.416 (15) |
C28—C29 | 1.491 (5) | C25—H25 | 0.9300 |
C11—H11A | 0.9700 | C15—H15A | 0.9600 |
C11—H11B | 0.9700 | C15—H15B | 0.9600 |
C11—C12 | 1.522 (5) | C15—H15C | 0.9600 |
C42—H42 | 0.9300 | C20—H20 | 0.9300 |
C2—C3 | 1.410 (5) | C20—C21 | 1.312 (16) |
C2—C7 | 1.428 (5) | C21—H21 | 0.9300 |
C27—H27A | 0.9700 | C23—H23 | 0.9300 |
C27—H27B | 0.9700 | C30—H30A | 0.9600 |
C27—C26 | 1.521 (5) | C30—H30B | 0.9600 |
C32—H32 | 0.9300 | C30—H30C | 0.9600 |
C34—O6—H6A | 115 (3) | C27—C26—H26A | 109.2 |
C37—O7—H7 | 115 (3) | C27—C26—H26B | 109.2 |
C40—O8—H8A | 113 (3) | H26A—C26—H26B | 107.9 |
C31—O5—H5A | 110 (3) | C16—C26—C27 | 112.1 (3) |
C4—O1—C15 | 118.8 (3) | C16—C26—H26A | 109.2 |
C13—N2—C12 | 122.8 (2) | C16—C26—H26B | 109.2 |
C13—N2—H2 | 121 (3) | C8—C7—C2 | 118.9 (4) |
C12—N2—H2 | 116 (3) | C6—C7—C2 | 118.3 (5) |
C28—N1—C27 | 122.9 (3) | C6—C7—C8 | 122.8 (5) |
C28—N1—H1 | 121 (3) | C19—C18—H18 | 119.8 |
C27—N1—H1 | 116 (3) | C19—C18—C17 | 120.4 (5) |
O6—C34—C33 | 117.8 (2) | C17—C18—H18 | 119.8 |
C35—C34—O6 | 123.1 (3) | O3—C19—C18 | 124.2 (6) |
C35—C34—C33 | 119.1 (3) | O3—C19—C20 | 118.2 (8) |
O2—C13—N2 | 121.7 (3) | C18—C19—C20 | 117.6 (9) |
O2—C13—C14 | 121.5 (3) | C4—C5—H5 | 119.5 |
N2—C13—C14 | 116.8 (3) | C6—C5—H5 | 119.5 |
C36—C31—O5 | 121.6 (3) | C6—C5—C4 | 121.0 (4) |
C36—C31—C32 | 119.7 (3) | C7—C8—H8 | 119.3 |
C32—C31—O5 | 118.7 (3) | C9—C8—C7 | 121.4 (4) |
O8—C40—C39 | 122.3 (3) | C9—C8—H8 | 119.3 |
C41—C40—O8 | 118.0 (3) | C28—C29—H29A | 109.5 |
C41—C40—C39 | 119.6 (2) | C28—C29—H29B | 109.5 |
C40—C41—H41 | 119.8 | C28—C29—H29C | 109.5 |
C40—C41—C42 | 120.4 (3) | H29A—C29—H29B | 109.5 |
C42—C41—H41 | 119.8 | H29A—C29—H29C | 109.5 |
C39—C38—H38 | 120.0 | H29B—C29—H29C | 109.5 |
C37—C38—H38 | 120.0 | C17—C16—C26 | 121.3 (3) |
C37—C38—C39 | 120.0 (3) | C25—C16—C26 | 118.8 (5) |
C34—C33—H33 | 119.8 | C25—C16—C17 | 119.9 (5) |
C32—C33—C34 | 120.5 (3) | O1—C4—C3 | 124.7 (4) |
C32—C33—H33 | 119.8 | O1—C4—C5 | 116.2 (4) |
C40—C39—C38 | 119.9 (3) | C3—C4—C5 | 119.1 (5) |
C40—C39—H39 | 120.0 | C18—C17—C16 | 122.1 (3) |
C38—C39—H39 | 120.0 | C18—C17—C22 | 119.5 (5) |
C2—C1—C11 | 121.1 (3) | C22—C17—C16 | 118.4 (5) |
C10—C1—C11 | 119.7 (3) | C13—C14—H14A | 109.5 |
C10—C1—C2 | 119.2 (3) | C13—C14—H14B | 109.5 |
O7—C37—C38 | 122.3 (2) | C13—C14—H14C | 109.5 |
O7—C37—C42 | 118.1 (2) | H14A—C14—H14B | 109.5 |
C42—C37—C38 | 119.6 (2) | H14A—C14—H14C | 109.5 |
C31—C36—H36 | 119.9 | H14B—C14—H14C | 109.5 |
C31—C36—C35 | 120.2 (3) | C7—C6—H6 | 119.1 |
C35—C36—H36 | 119.9 | C5—C6—C7 | 121.8 (4) |
O4—C28—N1 | 121.1 (3) | C5—C6—H6 | 119.1 |
O4—C28—C29 | 122.0 (3) | C8—C9—H9 | 120.1 |
N1—C28—C29 | 116.9 (3) | C8—C9—C10 | 119.8 (5) |
C1—C11—H11A | 108.8 | C10—C9—H9 | 120.1 |
C1—C11—H11B | 108.8 | C1—C10—H10 | 118.8 |
C1—C11—C12 | 113.8 (3) | C9—C10—C1 | 122.3 (5) |
H11A—C11—H11B | 107.7 | C9—C10—H10 | 118.8 |
C12—C11—H11A | 108.8 | C25—C24—H24 | 119.7 |
C12—C11—H11B | 108.8 | C23—C24—H24 | 119.7 |
C41—C42—C37 | 120.4 (3) | C23—C24—C25 | 120.6 (10) |
C41—C42—H42 | 119.8 | C17—C22—C21 | 118.2 (8) |
C37—C42—H42 | 119.8 | C23—C22—C17 | 118.2 (8) |
C1—C2—C7 | 118.4 (4) | C23—C22—C21 | 123.6 (8) |
C3—C2—C1 | 122.3 (3) | C16—C25—C24 | 119.9 (8) |
C3—C2—C7 | 119.3 (3) | C16—C25—H25 | 120.0 |
N1—C27—H27A | 109.2 | C24—C25—H25 | 120.0 |
N1—C27—H27B | 109.2 | O1—C15—H15A | 109.5 |
N1—C27—C26 | 111.8 (3) | O1—C15—H15B | 109.5 |
H27A—C27—H27B | 107.9 | O1—C15—H15C | 109.5 |
C26—C27—H27A | 109.2 | H15A—C15—H15B | 109.5 |
C26—C27—H27B | 109.2 | H15A—C15—H15C | 109.5 |
C31—C32—H32 | 119.8 | H15B—C15—H15C | 109.5 |
C33—C32—C31 | 120.5 (3) | C19—C20—H20 | 117.9 |
C33—C32—H32 | 119.8 | C21—C20—C19 | 124.2 (9) |
N2—C12—C11 | 111.4 (3) | C21—C20—H20 | 117.9 |
N2—C12—H12A | 109.3 | C22—C21—H21 | 119.9 |
N2—C12—H12B | 109.3 | C20—C21—C22 | 120.1 (7) |
C11—C12—H12A | 109.3 | C20—C21—H21 | 119.9 |
C11—C12—H12B | 109.3 | C24—C23—C22 | 122.9 (9) |
H12A—C12—H12B | 108.0 | C24—C23—H23 | 118.6 |
C19—O3—C30 | 117.0 (5) | C22—C23—H23 | 118.6 |
C34—C35—C36 | 120.1 (3) | O3—C30—H30A | 109.5 |
C34—C35—H35 | 119.9 | O3—C30—H30B | 109.5 |
C36—C35—H35 | 119.9 | O3—C30—H30C | 109.5 |
C2—C3—H3 | 119.8 | H30A—C30—H30B | 109.5 |
C4—C3—C2 | 120.4 (4) | H30A—C30—H30C | 109.5 |
C4—C3—H3 | 119.8 | H30B—C30—H30C | 109.5 |
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