Acta Cryst. (2008). E64, m984-m985 [ doi:10.1107/S1600536808019296 ]
![[kappa]](/logos/entities/kappa_rmgif.gif)
O)tris(picrato-2O1,O2)lanthanum(III) tri-2-pyridylamine solvateThe title compound, [La(C6H2N3O7)3(C2H6O)3]·C15H12N4, has two molecular building blocks, namely the neutral mononuclear adduct of lanthanum picrate with ethanol [i.e. La(pic)3:EtOH (1:3); La(pic)3 = lanthanum picrate and EtOH = ethanol] and the oligodentate aromatic nitrogen base tri-2-pyridylamine (tpa). The asymmetric unit contains two formula units. The compound was prepared during an investigation of the stereochemistry of lanthanoid picrate complexes with O-donor ligands. The metal-ligand adduct adopts a nine-coordinate tricapped trigonal-prismatic metal atom environment. The stereochemical arrangement of the ligands about the metal core is typical of a fac-isomer with stoichiometry M(bidentate)3(monodentate)3. Face-to-face hydrogen bonds are found between the tpa molecule and the ethanol ligands. One ethanol ligand is disordered over two positions, with site occupancy factors of ca 0.7 and 0.3. The oxygen atoms of a nitro group are also disordered over two positions; the site occupancy factors are ca 0.6 and 0.4.
Using a 1:1 mole ratio, hydrated La(pic)3 (Harrowfield et al.,, 1994) and tpa was dissolved in a suitable volume of 70% v/v ethanol in triethyl orthoformate (used in the synthesis as a dehydrating agent). The mixture was then heated under reflux for 1 h ensuring formation of complex is complete. The solution was then filtered while hot into a Shlenk tube fitted with vacuum and nitrogen outlet. The solvent was removed under vacuum until the contents were sufficiently concentrated, the product was then allowed to cool slowly until yellow crystals deposited.
All H atoms, with the exception of those associated with the hydroxy groups of the ethanol molecules, were positioned geometrically and refined using a riding model with C—H = 0.95–0.99 Å, and with Uiso(H) = 1.2 (1.5 for methyl groups) times Ueq(C). The hydroxy H atoms of the ethanol molecules were, in the early stages of refinement, built geometrically as idealized OH groups and refined using a riding model (allowing rotation about the C—O bond) until the mean shift/e.s.d. was at a minimum of 0.01, with the C—O—H angle tetrahedral and O—H = 0.80–0.85 Å, and with Uiso(H) = 1.5 times Ueq(O). A further five final cycles of refinement were performed with the hydroxy H atom positions fixed in order to allow hydroxy oxygen atom to lanthanum metal atom bond lengths with associated angles to be included in the connectivity list. Quasi-in-plane orientational disorder was exhibited for the totality of ethanol ligand "03" (with the exception of its La-bound oxygen atom "O031"). All 1,2– and 1,3– distances for the disordered atoms were restrained so that both fragments would have similar geometries (i.e. the SAME restraint, using the default 0.02 s.u. values). The sum of the site occupation parameters for both disordered groups was constrained to unity during refinement giving a major site occupation component value of 0.664 (8) with that of the minor component value complementary. All atoms of the disordered ethanol group closer than 1.7 Å were restrained to have similar Uij components (i.e. the SIMU restraint was applied) with the default 0.04 (central C atom) and 0.08 (terminal C and O atoms) s.u. values. The oxygen atoms of the "36" picrate nitro group exhibit rotational disorder around the N—C bond. During refinement the N—O distances were restrained to be the same (i.e. the SADI restraint, using the default 0.02 s.u. value) and atoms of each of the CNO2 fragments (atoms C36 and N36 both being a part of each planar group) were restrained to lie in a common plane (i.e. the FLAT restraint, using the default 0.1 s.u. value). The sum of site occupancies was constrained to unity, oxygen fragments refining to a major site occupation value of 0.58 (2) with a minor component value complementary. All atoms of the disordered nitro group closer than 1.7 Å were restrained to have similar Uij components (i.e. the SIMU restraint was applied) with the default 0.04 (central N atom) and 0.08 (terminal O atoms) s.u. values.
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Xtal3.7 (Hall et al., 2001); software used to prepare material for publication: Xtal3.7 (Hall et al., 2001).
![[Figure 1]](./zl2121fig1thm.gif)
| Fig. 1. View of the molecular structure of (I) depicting the tris(2-pyridyl)amine molecule interacting with the (C6H2N3O7-O,O')3(C2H6O-O)3La(III) adduct through O—H···N hydrogen bonds. 50% probability displacement ellipsoids are shown for non-H atoms. Enhanced figure is accessible at http://submission.iucr.org/jtkt/serve/z/u4xwab7OUyDKQ3um/zz0000/0/ |
![[Figure 2]](./zl2121fig2thm.gif)
| Fig. 2. Labelled ORTEP diagram of the tris(ethanol-O)tris(picrato-O,O')lanthanum(III) neutral mononuclear adduct projected through the triangular faces of its 9-coordinate tri-capped trigonal prismatic metal environment. 50% probability displacement ellipsoids are shown for non-H atoms. |
![[Figure 3]](./zl2121fig3thm.gif)
| Fig. 3. Packing diagram of (I) viewed down the c-axis. The O—H···N hydrogen bonds are shown as dotted lines. 50% probability displacement ellipsoids are shown for non-H atoms. |
| [La(C6H2N3O7)3(C2H6O)3]·C15H12N4 | Z = 4 |
| Mr = 1209.69 | F000 = 2440 |
| Triclinic, P1 | Dx = 1.672 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation λ = 0.71073 Å |
| a = 15.7554 (19) Å | Cell parameters from 16526 reflections |
| b = 16.4752 (14) Å | θ = 2.6–31.2º |
| c = 20.427 (4) Å | µ = 0.99 mm−1 |
| α = 101.714 (11)º | T = 100 (2) K |
| β = 111.610 (14)º | Plate, yellow |
| γ = 90.676 (8)º | 0.50 × 0.18 × 0.03 mm |
| V = 4805.1 (13) Å3 |
| Oxford Diffraction Xcalibur diffractometer | 28469 independent reflections |
| Radiation source: fine-focus sealed tube | 14209 reflections with I > 2σ(I) |
| Monochromator: graphite | Rint = 0.049 |
| Detector resolution: 16.0009 pixels mm-1 | θmax = 31.2º |
| T = 100(2) K | θmin = 2.6º |
| ω scans | h = −22→22 |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | k = −23→23 |
| Tmin = 0.773, Tmax = 0.970 | l = −29→29 |
| 58832 measured reflections |
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
| R[F2 > 2σ(F2)] = 0.043 | H-atom parameters constrained |
| wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.031P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 0.84 | (Δ/σ)max = 0.047 |
| 28469 reflections | Δρmax = 2.85 e Å−3 |
| 1419 parameters | Δρmin = −0.75 e Å−3 |
| 104 restraints | Extinction correction: none |
| Primary atom site location: structure-invariant direct methods |
| [La(C6H2N3O7)3(C2H6O)3]·C15H12N4 | γ = 90.676 (8)º |
| Mr = 1209.69 | V = 4805.1 (13) Å3 |
| Triclinic, P1 | Z = 4 |
| a = 15.7554 (19) Å | Mo Kα |
| b = 16.4752 (14) Å | µ = 0.99 mm−1 |
| c = 20.427 (4) Å | T = 100 (2) K |
| α = 101.714 (11)º | 0.50 × 0.18 × 0.03 mm |
| β = 111.610 (14)º |
| Oxford Diffraction Xcalibur diffractometer | 28469 independent reflections |
| Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2006) | 14209 reflections with I > 2σ(I) |
| Tmin = 0.773, Tmax = 0.970 | Rint = 0.049 |
| 58832 measured reflections |
| R[F2 > 2σ(F2)] = 0.043 | 104 restraints |
| wR(F2) = 0.086 | H-atom parameters constrained |
| S = 0.84 | Δρmax = 2.85 e Å−3 |
| 28469 reflections | Δρmin = −0.75 e Å−3 |
| 1419 parameters |
Experimental. CrysAlis RED (Oxford Diffraction, 2006) Empirical absorption correction using spherical harmonics as implemented in the SCALE3 ABSPACK scaling algorithm. |
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes. |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| La1 | 0.860784 (13) | 0.552421 (12) | 0.752304 (10) | 0.01733 (5) | |
| O11 | 0.84562 (14) | 0.40793 (13) | 0.69097 (11) | 0.0192 (5) | |
| C11 | 0.8443 (2) | 0.33456 (19) | 0.70167 (17) | 0.0162 (7) | |
| C12 | 0.8586 (2) | 0.31263 (19) | 0.76897 (18) | 0.0192 (7) | |
| C13 | 0.8654 (2) | 0.2323 (2) | 0.7780 (2) | 0.0231 (8) | |
| H13 | 0.8804 | 0.2213 | 0.8247 | 0.028* | |
| C14 | 0.8503 (2) | 0.16812 (19) | 0.71953 (19) | 0.0203 (7) | |
| C15 | 0.8328 (2) | 0.1827 (2) | 0.65141 (19) | 0.0211 (8) | |
| H15 | 0.8232 | 0.1379 | 0.6112 | 0.025* | |
| C16 | 0.8296 (2) | 0.2627 (2) | 0.64365 (18) | 0.0193 (7) | |
| N12 | 0.86660 (19) | 0.37655 (18) | 0.83211 (16) | 0.0244 (7) | |
| O121 | 0.83658 (16) | 0.44447 (14) | 0.82365 (12) | 0.0256 (5) | |
| O122 | 0.89884 (19) | 0.36014 (15) | 0.89202 (13) | 0.0386 (7) | |
| N14 | 0.84826 (19) | 0.08238 (18) | 0.7297 (2) | 0.0295 (8) | |
| O141 | 0.87984 (16) | 0.06817 (16) | 0.78795 (16) | 0.0373 (7) | |
| O142 | 0.81122 (16) | 0.02741 (14) | 0.67350 (14) | 0.0303 (6) | |
| N16 | 0.8119 (2) | 0.27897 (17) | 0.57155 (15) | 0.0238 (7) | |
| O161 | 0.75047 (17) | 0.32233 (15) | 0.54706 (13) | 0.0333 (6) | |
| O162 | 0.86114 (17) | 0.24768 (15) | 0.54005 (13) | 0.0340 (6) | |
| O21 | 0.95890 (14) | 0.55337 (14) | 0.68478 (12) | 0.0227 (5) | |
| C21 | 0.9606 (2) | 0.5047 (2) | 0.62887 (19) | 0.0234 (8) | |
| C22 | 0.8859 (2) | 0.4847 (2) | 0.56022 (18) | 0.0221 (8) | |
| C23 | 0.8899 (3) | 0.4340 (2) | 0.49848 (19) | 0.0286 (9) | |
| H23 | 0.8392 | 0.4252 | 0.4536 | 0.034* | |
| C24 | 0.9694 (3) | 0.3969 (2) | 0.5041 (2) | 0.0294 (9) | |
| C25 | 1.0435 (3) | 0.4080 (2) | 0.5692 (2) | 0.0317 (9) | |
| H25 | 1.0963 | 0.3793 | 0.5728 | 0.038* | |
| C26 | 1.0389 (2) | 0.4614 (2) | 0.6284 (2) | 0.0246 (8) | |
| N22 | 0.7984 (2) | 0.51949 (17) | 0.55199 (17) | 0.0259 (7) | |
| O221 | 0.77665 (15) | 0.53675 (14) | 0.60512 (12) | 0.0256 (6) | |
| O222 | 0.74856 (18) | 0.52775 (17) | 0.49225 (14) | 0.0414 (7) | |
| N24 | 0.9739 (3) | 0.3425 (2) | 0.4392 (2) | 0.0439 (10) | |
| O241 | 0.9067 (2) | 0.33343 (19) | 0.38276 (18) | 0.0616 (10) | |
| O242 | 1.0466 (2) | 0.31122 (18) | 0.44525 (17) | 0.0598 (9) | |
| N26 | 1.1194 (2) | 0.4714 (2) | 0.69646 (18) | 0.0330 (8) | |
| O261 | 1.14614 (16) | 0.54218 (16) | 0.73386 (14) | 0.0362 (7) | |
| O262 | 1.15419 (18) | 0.40807 (18) | 0.71157 (16) | 0.0479 (8) | |
| O31 | 1.00390 (15) | 0.51721 (13) | 0.83415 (12) | 0.0236 (5) | |
| C31 | 1.0896 (2) | 0.5396 (2) | 0.86261 (18) | 0.0206 (8) | |
| C32 | 1.1283 (2) | 0.62516 (19) | 0.88504 (17) | 0.0170 (7) | |
| C33 | 1.2209 (2) | 0.6484 (2) | 0.92038 (17) | 0.0213 (8) | |
| H33 | 1.2434 | 0.7056 | 0.9348 | 0.026* | |
| C34 | 1.2801 (2) | 0.5889 (2) | 0.93453 (19) | 0.0242 (8) | |
| C35 | 1.2499 (2) | 0.5048 (2) | 0.91411 (19) | 0.0261 (8) | |
| H35 | 1.2922 | 0.4641 | 0.9247 | 0.031* | |
| C36 | 1.1579 (2) | 0.48161 (19) | 0.87832 (19) | 0.0248 (8) | |
| N32 | 1.0704 (2) | 0.69303 (17) | 0.86917 (15) | 0.0219 (6) | |
| O321 | 0.98921 (15) | 0.67753 (13) | 0.82651 (13) | 0.0247 (5) | |
| O322 | 1.10475 (15) | 0.76525 (14) | 0.89742 (13) | 0.0278 (6) | |
| N34 | 1.37835 (19) | 0.61448 (19) | 0.97202 (16) | 0.0254 (7) | |
| O341 | 1.40413 (15) | 0.68896 (15) | 0.99330 (13) | 0.0298 (6) | |
| O342 | 1.43025 (16) | 0.55841 (15) | 0.98042 (14) | 0.0350 (6) | |
| N36 | 1.1311 (2) | 0.39154 (18) | 0.85566 (18) | 0.0359 (8) | |
| O361 | 1.0590 (7) | 0.3646 (14) | 0.8045 (8) | 0.039 (3) | 0.59 (2) |
| O362 | 1.1776 (6) | 0.3455 (4) | 0.8937 (7) | 0.048 (3) | 0.59 (2) |
| O363 | 1.0508 (9) | 0.366 (2) | 0.8229 (11) | 0.039 (3) | 0.41 (2) |
| O364 | 1.1983 (6) | 0.3466 (5) | 0.8618 (9) | 0.034 (4) | 0.41 (2) |
| O011 | 0.69116 (14) | 0.52258 (13) | 0.71509 (12) | 0.0237 (5) | |
| H011 | 0.6645 | 0.5450 | 0.7419 | 0.036* | |
| C011 | 0.6261 (2) | 0.4638 (2) | 0.65326 (19) | 0.0256 (8) | |
| H01A | 0.6566 | 0.4406 | 0.6199 | 0.031* | |
| H01B | 0.5745 | 0.4934 | 0.6270 | 0.031* | |
| C012 | 0.5896 (3) | 0.3944 (3) | 0.6747 (2) | 0.0548 (13) | |
| H01C | 0.5463 | 0.3563 | 0.6315 | 0.082* | |
| H01D | 0.5580 | 0.4169 | 0.7068 | 0.082* | |
| H01E | 0.6403 | 0.3643 | 0.7000 | 0.082* | |
| O021 | 0.81139 (14) | 0.68541 (13) | 0.71535 (12) | 0.0208 (5) | |
| H021 | 0.7554 | 0.6928 | 0.7001 | 0.031* | |
| C021 | 0.8602 (2) | 0.7417 (2) | 0.69256 (19) | 0.0235 (8) | |
| H02A | 0.9150 | 0.7164 | 0.6879 | 0.028* | |
| H02B | 0.8814 | 0.7942 | 0.7299 | 0.028* | |
| C022 | 0.8015 (2) | 0.7608 (2) | 0.6218 (2) | 0.0332 (9) | |
| H02C | 0.8372 | 0.7986 | 0.6081 | 0.050* | |
| H02D | 0.7481 | 0.7872 | 0.6265 | 0.050* | |
| H02E | 0.7811 | 0.7090 | 0.5845 | 0.050* | |
| O031 | 0.83140 (16) | 0.62240 (13) | 0.86196 (12) | 0.0261 (6) | 0.661 (8) |
| H031 | 0.8010 | 0.6632 | 0.8534 | 0.039* | 0.661 (8) |
| C031 | 0.8293 (4) | 0.6018 (3) | 0.9284 (3) | 0.0241 (15) | 0.661 (8) |
| H03A | 0.7930 | 0.5477 | 0.9169 | 0.029* | 0.661 (8) |
| H03B | 0.8015 | 0.6453 | 0.9529 | 0.029* | 0.661 (8) |
| C032 | 0.9264 (4) | 0.5973 (4) | 0.9753 (3) | 0.0297 (17) | 0.661 (8) |
| H03C | 0.9288 | 0.5841 | 1.0206 | 0.044* | 0.661 (8) |
| H03D | 0.9614 | 0.6511 | 0.9858 | 0.044* | 0.661 (8) |
| H03E | 0.9528 | 0.5539 | 0.9504 | 0.044* | 0.661 (8) |
| O033 | 0.83140 (16) | 0.62240 (13) | 0.86196 (12) | 0.0261 (6) | 0.339 (8) |
| H033 | 0.8123 | 0.6698 | 0.8628 | 0.039* | 0.339 (8) |
| C033 | 0.9030 (7) | 0.6198 (7) | 0.9377 (5) | 0.023 (3) | 0.339 (8) |
| H03F | 0.9475 | 0.5793 | 0.9331 | 0.028* | 0.339 (8) |
| H03G | 0.9369 | 0.6753 | 0.9623 | 0.028* | 0.339 (8) |
| C034 | 0.8519 (7) | 0.5942 (8) | 0.9799 (6) | 0.039 (4) | 0.339 (8) |
| H03H | 0.8952 | 0.5926 | 1.0284 | 0.058* | 0.339 (8) |
| H03I | 0.8193 | 0.5389 | 0.9554 | 0.058* | 0.339 (8) |
| H03J | 0.8077 | 0.6344 | 0.9837 | 0.058* | 0.339 (8) |
| N100 | 0.63018 (17) | 0.71629 (16) | 0.77801 (14) | 0.0186 (6) | |
| N111 | 0.60883 (17) | 0.59039 (17) | 0.80784 (15) | 0.0206 (6) | |
| C112 | 0.5936 (2) | 0.5476 (2) | 0.85276 (19) | 0.0249 (8) | |
| H112 | 0.5883 | 0.4884 | 0.8397 | 0.030* | |
| C113 | 0.5853 (2) | 0.5851 (2) | 0.91656 (19) | 0.0240 (8) | |
| H113 | 0.5734 | 0.5526 | 0.9462 | 0.029* | |
| C114 | 0.5945 (2) | 0.6707 (2) | 0.93635 (19) | 0.0256 (8) | |
| H114 | 0.5903 | 0.6982 | 0.9805 | 0.031* | |
| C115 | 0.6101 (2) | 0.7161 (2) | 0.89125 (18) | 0.0244 (8) | |
| H115 | 0.6160 | 0.7753 | 0.9034 | 0.029* | |
| C116 | 0.6169 (2) | 0.6733 (2) | 0.82803 (17) | 0.0178 (7) | |
| N121 | 0.62439 (18) | 0.68932 (16) | 0.65925 (15) | 0.0220 (6) | |
| C122 | 0.5771 (2) | 0.6647 (2) | 0.58794 (19) | 0.0248 (8) | |
| H122 | 0.6083 | 0.6678 | 0.5565 | 0.030* | |
| C123 | 0.4864 (2) | 0.6354 (2) | 0.5580 (2) | 0.0296 (9) | |
| H123 | 0.4560 | 0.6169 | 0.5071 | 0.035* | |
| C124 | 0.4395 (2) | 0.6333 (2) | 0.6038 (2) | 0.0277 (8) | |
| H124 | 0.3765 | 0.6132 | 0.5847 | 0.033* | |
| C125 | 0.4861 (2) | 0.6609 (2) | 0.67723 (19) | 0.0227 (8) | |
| H125 | 0.4556 | 0.6610 | 0.7096 | 0.027* | |
| C126 | 0.5789 (2) | 0.68842 (19) | 0.70310 (17) | 0.0184 (7) | |
| N131 | 0.77762 (18) | 0.77605 (16) | 0.85513 (14) | 0.0206 (6) | |
| C132 | 0.8455 (2) | 0.8387 (2) | 0.87808 (19) | 0.0254 (8) | |
| H132 | 0.9014 | 0.8348 | 0.9162 | 0.030* | |
| C133 | 0.8375 (2) | 0.9074 (2) | 0.84895 (18) | 0.0241 (8) | |
| H133 | 0.8874 | 0.9491 | 0.8651 | 0.029* | |
| C134 | 0.7552 (2) | 0.9146 (2) | 0.79552 (19) | 0.0259 (8) | |
| H134 | 0.7477 | 0.9620 | 0.7748 | 0.031* | |
| C135 | 0.6838 (2) | 0.8532 (2) | 0.77220 (18) | 0.0226 (8) | |
| H135 | 0.6263 | 0.8575 | 0.7360 | 0.027* | |
| C136 | 0.6987 (2) | 0.78497 (19) | 0.80338 (17) | 0.0178 (7) | |
| La2 | 0.633752 (13) | 0.916258 (12) | 0.243353 (10) | 0.01671 (5) | |
| O41 | 0.64846 (14) | 0.80202 (14) | 0.30240 (11) | 0.0198 (5) | |
| C41 | 0.6527 (2) | 0.7237 (2) | 0.29249 (18) | 0.0219 (8) | |
| C42 | 0.6402 (2) | 0.66825 (19) | 0.22517 (17) | 0.0172 (7) | |
| C43 | 0.6363 (2) | 0.5827 (2) | 0.21597 (19) | 0.0207 (7) | |
| H43 | 0.6237 | 0.5480 | 0.1696 | 0.025* | |
| C44 | 0.6511 (2) | 0.5485 (2) | 0.27501 (19) | 0.0207 (7) | |
| C45 | 0.6658 (2) | 0.5979 (2) | 0.34318 (18) | 0.0219 (8) | |
| H45 | 0.6743 | 0.5736 | 0.3832 | 0.026* | |
| C46 | 0.6676 (2) | 0.6820 (2) | 0.35048 (17) | 0.0175 (7) | |
| N42 | 0.63182 (18) | 0.69970 (17) | 0.16134 (15) | 0.0206 (6) | |
| O421 | 0.65665 (15) | 0.77426 (13) | 0.16916 (12) | 0.0226 (5) | |
| O422 | 0.60455 (17) | 0.65152 (15) | 0.10237 (13) | 0.0335 (6) | |
| N44 | 0.65393 (18) | 0.45574 (17) | 0.26500 (17) | 0.0196 (6) | |
| O441 | 0.62705 (16) | 0.41551 (15) | 0.20558 (16) | 0.0340 (7) | |
| O442 | 0.68841 (16) | 0.43226 (14) | 0.32138 (14) | 0.0306 (6) | |
| N46 | 0.6819 (2) | 0.73521 (18) | 0.42171 (16) | 0.0262 (7) | |
| O461 | 0.74305 (17) | 0.79230 (15) | 0.44626 (13) | 0.0338 (6) | |
| O462 | 0.63206 (17) | 0.71809 (16) | 0.45197 (13) | 0.0366 (6) | |
| O51 | 0.53601 (14) | 0.94981 (13) | 0.31108 (12) | 0.0215 (5) | |
| C51 | 0.5352 (2) | 0.93254 (19) | 0.36869 (18) | 0.0184 (7) | |
| C52 | 0.6101 (2) | 0.9501 (2) | 0.43716 (18) | 0.0219 (8) | |
| C53 | 0.6056 (2) | 0.9327 (2) | 0.49947 (18) | 0.0249 (8) | |
| H53 | 0.6565 | 0.9479 | 0.5441 | 0.030* | |
| C54 | 0.5259 (3) | 0.8932 (2) | 0.49544 (19) | 0.0263 (8) | |
| C55 | 0.4513 (2) | 0.8701 (2) | 0.4309 (2) | 0.0265 (8) | |
| H55 | 0.3977 | 0.8406 | 0.4285 | 0.032* | |
| C56 | 0.4557 (2) | 0.8906 (2) | 0.37010 (19) | 0.0229 (8) | |
| N52 | 0.6967 (2) | 0.98864 (17) | 0.44359 (17) | 0.0251 (7) | |
| O521 | 0.71871 (14) | 0.97801 (14) | 0.39039 (12) | 0.0234 (5) | |
| O522 | 0.74768 (17) | 1.02960 (15) | 0.50342 (14) | 0.0354 (6) | |
| N54 | 0.5208 (3) | 0.8752 (2) | 0.56113 (19) | 0.0368 (8) | |
| O541 | 0.5884 (2) | 0.89389 (19) | 0.61692 (15) | 0.0522 (8) | |
| O542 | 0.4460 (2) | 0.84492 (18) | 0.55689 (15) | 0.0500 (8) | |
| N56 | 0.37638 (19) | 0.8642 (2) | 0.30236 (16) | 0.0283 (7) | |
| O561 | 0.34683 (16) | 0.91519 (16) | 0.26496 (13) | 0.0335 (6) | |
| O562 | 0.34174 (17) | 0.79208 (17) | 0.28666 (15) | 0.0445 (7) | |
| O61 | 0.49117 (14) | 0.83816 (13) | 0.15971 (12) | 0.0204 (5) | |
| C61 | 0.4058 (2) | 0.8434 (2) | 0.13435 (17) | 0.0180 (7) | |
| C62 | 0.3641 (2) | 0.9168 (2) | 0.11297 (18) | 0.0207 (8) | |
| C63 | 0.2705 (2) | 0.9208 (2) | 0.08079 (17) | 0.0196 (7) | |
| H63 | 0.2467 | 0.9701 | 0.0669 | 0.023* | |
| C64 | 0.2121 (2) | 0.8507 (2) | 0.06938 (16) | 0.0174 (7) | |
| C65 | 0.2457 (2) | 0.7779 (2) | 0.08790 (17) | 0.0191 (7) | |
| H65 | 0.2050 | 0.7303 | 0.0789 | 0.023* | |
| C66 | 0.3380 (2) | 0.7753 (2) | 0.11914 (18) | 0.0212 (7) | |
| N62 | 0.42103 (18) | 0.99304 (16) | 0.12567 (15) | 0.0194 (6) | |
| O621 | 0.50192 (15) | 1.00287 (13) | 0.16861 (12) | 0.0230 (5) | |
| O622 | 0.38583 (15) | 1.04725 (14) | 0.09305 (13) | 0.0316 (6) | |
| N64 | 0.11342 (18) | 0.85389 (18) | 0.03600 (15) | 0.0227 (7) | |
| O641 | 0.08434 (15) | 0.91680 (14) | 0.01608 (13) | 0.0265 (6) | |
| O642 | 0.06349 (15) | 0.79255 (15) | 0.03100 (13) | 0.0315 (6) | |
| N66 | 0.3699 (2) | 0.69686 (18) | 0.13932 (17) | 0.0275 (7) | |
| O661 | 0.44218 (16) | 0.69852 (15) | 0.19101 (15) | 0.0351 (6) | |
| O662 | 0.32053 (17) | 0.63251 (15) | 0.10357 (15) | 0.0397 (7) | |
| O041 | 0.80292 (14) | 0.90418 (13) | 0.28443 (11) | 0.0210 (5) | |
| H041 | 0.8297 | 0.9108 | 0.2569 | 0.031* | |
| C041 | 0.8663 (2) | 0.8781 (2) | 0.34645 (19) | 0.0250 (8) | |
| H04A | 0.8338 | 0.8681 | 0.3777 | 0.030* | |
| H04B | 0.9160 | 0.9234 | 0.3748 | 0.030* | |
| C042 | 0.9081 (3) | 0.7998 (2) | 0.3252 (2) | 0.0490 (12) | |
| H04C | 0.9498 | 0.7840 | 0.3688 | 0.073* | |
| H04D | 0.9422 | 0.8101 | 0.2957 | 0.073* | |
| H04E | 0.8592 | 0.7547 | 0.2974 | 0.073* | |
| O051 | 0.68822 (14) | 1.06876 (12) | 0.27962 (12) | 0.0190 (5) | |
| H051 | 0.7450 | 1.0827 | 0.2983 | 0.028* | |
| C051 | 0.6404 (2) | 1.13673 (19) | 0.30115 (18) | 0.0215 (8) | |
| H05A | 0.5846 | 1.1141 | 0.3053 | 0.026* | |
| H05B | 0.6210 | 1.1697 | 0.2635 | 0.026* | |
| C052 | 0.6994 (2) | 1.1925 (2) | 0.37188 (19) | 0.0288 (9) | |
| H05C | 0.6648 | 1.2378 | 0.3848 | 0.043* | |
| H05D | 0.7542 | 1.2158 | 0.3676 | 0.043* | |
| H05E | 0.7178 | 1.1603 | 0.4095 | 0.043* | |
| O061 | 0.67246 (14) | 0.93827 (13) | 0.13884 (12) | 0.0204 (5) | |
| H061 | 0.6920 | 0.9875 | 0.1431 | 0.031* | |
| C061 | 0.6547 (2) | 0.8914 (2) | 0.06678 (17) | 0.0217 (8) | |
| H06A | 0.6791 | 0.8365 | 0.0689 | 0.026* | |
| H06B | 0.6864 | 0.9214 | 0.0436 | 0.026* | |
| C062 | 0.5527 (2) | 0.8792 (2) | 0.02221 (19) | 0.0268 (8) | |
| H06C | 0.5417 | 0.8463 | −0.0264 | 0.040* | |
| H06D | 0.5290 | 0.9335 | 0.0189 | 0.040* | |
| H06E | 0.5214 | 0.8497 | 0.0453 | 0.040* | |
| N200 | 0.87961 (17) | 0.07030 (16) | 0.22678 (14) | 0.0190 (6) | |
| N241 | 0.88834 (17) | −0.07251 (16) | 0.19476 (15) | 0.0186 (6) | |
| C242 | 0.8960 (2) | −0.1403 (2) | 0.14801 (19) | 0.0231 (8) | |
| H242 | 0.8947 | −0.1932 | 0.1596 | 0.028* | |
| C243 | 0.9055 (2) | −0.1362 (2) | 0.08426 (19) | 0.0244 (8) | |
| H243 | 0.9108 | −0.1849 | 0.0525 | 0.029* | |
| C244 | 0.9072 (2) | −0.0592 (2) | 0.06807 (18) | 0.0230 (8) | |
| H244 | 0.9137 | −0.0544 | 0.0245 | 0.028* | |
| C245 | 0.8995 (2) | 0.0114 (2) | 0.11468 (17) | 0.0199 (7) | |
| H245 | 0.9007 | 0.0648 | 0.1042 | 0.024* | |
| C246 | 0.8900 (2) | 0.0010 (2) | 0.17702 (18) | 0.0194 (7) | |
| N251 | 0.87729 (18) | 0.09980 (16) | 0.34369 (15) | 0.0215 (6) | |
| C252 | 0.9208 (2) | 0.1091 (2) | 0.41534 (18) | 0.0233 (8) | |
| H252 | 0.8872 | 0.1256 | 0.4453 | 0.028* | |
| C253 | 1.0108 (2) | 0.0960 (2) | 0.44737 (19) | 0.0292 (9) | |
| H253 | 1.0391 | 0.1036 | 0.4983 | 0.035* | |
| C254 | 1.0599 (2) | 0.0713 (2) | 0.40365 (19) | 0.0280 (8) | |
| H254 | 1.1220 | 0.0599 | 0.4243 | 0.034* | |
| C255 | 1.0178 (2) | 0.0635 (2) | 0.33003 (18) | 0.0233 (8) | |
| H255 | 1.0504 | 0.0486 | 0.2991 | 0.028* | |
| C256 | 0.9253 (2) | 0.07830 (19) | 0.30257 (18) | 0.0189 (7) | |
| N261 | 0.73700 (17) | 0.09295 (16) | 0.14540 (14) | 0.0188 (6) | |
| C262 | 0.6732 (2) | 0.1446 (2) | 0.12181 (19) | 0.0255 (8) | |
| H262 | 0.6195 | 0.1223 | 0.0805 | 0.031* | |
| C263 | 0.6803 (2) | 0.2279 (2) | 0.15349 (19) | 0.0279 (8) | |
| H263 | 0.6318 | 0.2613 | 0.1363 | 0.033* | |
| C264 | 0.7607 (2) | 0.2612 (2) | 0.21132 (19) | 0.0242 (8) | |
| H264 | 0.7685 | 0.3185 | 0.2345 | 0.029* | |
| C265 | 0.8291 (2) | 0.21070 (19) | 0.23486 (17) | 0.0200 (7) | |
| H265 | 0.8856 | 0.2328 | 0.2732 | 0.024* | |
| C266 | 0.8138 (2) | 0.1269 (2) | 0.20160 (17) | 0.0175 (7) |
| U11 | U22 | U33 | U12 | U13 | U23 | |
| La1 | 0.01984 (11) | 0.01524 (11) | 0.01523 (11) | 0.00090 (8) | 0.00573 (9) | 0.00149 (8) |
| O11 | 0.0287 (13) | 0.0140 (12) | 0.0118 (12) | −0.0005 (9) | 0.0047 (10) | 0.0019 (10) |
| C11 | 0.0182 (17) | 0.0146 (18) | 0.0135 (18) | −0.0008 (13) | 0.0053 (14) | −0.0005 (14) |
| C12 | 0.0186 (17) | 0.0147 (17) | 0.021 (2) | −0.0002 (13) | 0.0051 (15) | 0.0013 (15) |
| C13 | 0.0160 (17) | 0.025 (2) | 0.030 (2) | 0.0045 (14) | 0.0088 (16) | 0.0090 (17) |
| C14 | 0.0215 (17) | 0.0109 (17) | 0.029 (2) | 0.0007 (13) | 0.0093 (16) | 0.0069 (15) |
| C15 | 0.0221 (18) | 0.0173 (18) | 0.026 (2) | 0.0030 (14) | 0.0123 (16) | 0.0027 (15) |
| C16 | 0.0193 (17) | 0.0178 (18) | 0.0192 (19) | 0.0009 (13) | 0.0058 (15) | 0.0034 (15) |
| N12 | 0.0276 (16) | 0.0204 (17) | 0.0254 (18) | −0.0024 (13) | 0.0097 (14) | 0.0065 (14) |
| O121 | 0.0415 (15) | 0.0174 (13) | 0.0232 (14) | 0.0038 (11) | 0.0181 (12) | 0.0048 (11) |
| O122 | 0.0666 (19) | 0.0282 (15) | 0.0176 (15) | 0.0025 (13) | 0.0105 (14) | 0.0083 (12) |
| N14 | 0.0156 (16) | 0.0208 (17) | 0.050 (2) | −0.0010 (13) | 0.0167 (16) | −0.0034 (17) |
| O141 | 0.0266 (14) | 0.0346 (16) | 0.059 (2) | 0.0072 (11) | 0.0092 (14) | 0.0413 (15) |
| O142 | 0.0330 (14) | 0.0181 (14) | 0.0419 (17) | 0.0038 (11) | 0.0164 (13) | 0.0072 (12) |
| N16 | 0.0319 (17) | 0.0166 (16) | 0.0159 (16) | −0.0054 (13) | 0.0049 (14) | −0.0033 (13) |
| O161 | 0.0430 (16) | 0.0284 (15) | 0.0223 (15) | 0.0105 (12) | 0.0052 (13) | 0.0056 (12) |
| O162 | 0.0443 (16) | 0.0328 (15) | 0.0259 (15) | 0.0027 (12) | 0.0186 (13) | −0.0015 (12) |
| O21 | 0.0258 (13) | 0.0267 (14) | 0.0153 (13) | −0.0021 (10) | 0.0111 (11) | −0.0025 (11) |
| C21 | 0.033 (2) | 0.0173 (18) | 0.026 (2) | −0.0058 (15) | 0.0192 (18) | 0.0026 (16) |
| C22 | 0.031 (2) | 0.0229 (19) | 0.0126 (19) | −0.0035 (15) | 0.0101 (16) | 0.0009 (15) |
| C23 | 0.045 (2) | 0.0204 (19) | 0.020 (2) | −0.0112 (17) | 0.0147 (18) | −0.0022 (16) |
| C24 | 0.046 (2) | 0.024 (2) | 0.025 (2) | −0.0113 (17) | 0.027 (2) | −0.0074 (16) |
| C25 | 0.040 (2) | 0.018 (2) | 0.044 (3) | −0.0038 (16) | 0.029 (2) | −0.0016 (18) |
| C26 | 0.0218 (18) | 0.0221 (19) | 0.030 (2) | −0.0048 (15) | 0.0130 (17) | 0.0002 (16) |
| N22 | 0.0291 (18) | 0.0249 (17) | 0.0211 (19) | 0.0020 (13) | 0.0074 (15) | 0.0036 (14) |
| O221 | 0.0267 (13) | 0.0288 (14) | 0.0185 (14) | 0.0031 (10) | 0.0056 (11) | 0.0049 (11) |
| O222 | 0.0450 (17) | 0.0543 (19) | 0.0138 (15) | 0.0095 (14) | −0.0029 (13) | 0.0099 (13) |
| N24 | 0.075 (3) | 0.0246 (19) | 0.038 (2) | −0.0117 (19) | 0.037 (2) | −0.0106 (17) |
| O241 | 0.079 (2) | 0.063 (2) | 0.035 (2) | −0.0212 (18) | 0.0286 (19) | −0.0181 (17) |
| O242 | 0.083 (2) | 0.049 (2) | 0.063 (2) | 0.0098 (17) | 0.053 (2) | −0.0055 (17) |
| N26 | 0.0261 (18) | 0.039 (2) | 0.037 (2) | −0.0019 (16) | 0.0168 (16) | 0.0081 (18) |
| O261 | 0.0342 (15) | 0.0360 (17) | 0.0351 (17) | −0.0069 (12) | 0.0152 (13) | −0.0028 (14) |
| O262 | 0.0366 (16) | 0.0430 (18) | 0.059 (2) | 0.0121 (14) | 0.0115 (15) | 0.0115 (16) |
| O31 | 0.0229 (13) | 0.0181 (13) | 0.0240 (14) | 0.0019 (10) | 0.0019 (11) | 0.0053 (11) |
| C31 | 0.027 (2) | 0.0204 (19) | 0.0133 (18) | 0.0027 (15) | 0.0064 (16) | 0.0040 (15) |
| C32 | 0.0235 (18) | 0.0128 (17) | 0.0120 (18) | 0.0038 (13) | 0.0051 (15) | −0.0001 (14) |
| C33 | 0.0250 (19) | 0.0184 (18) | 0.0185 (19) | −0.0001 (14) | 0.0062 (16) | 0.0039 (15) |
| C34 | 0.0224 (19) | 0.025 (2) | 0.024 (2) | 0.0021 (15) | 0.0079 (16) | 0.0043 (16) |
| C35 | 0.027 (2) | 0.025 (2) | 0.029 (2) | 0.0093 (15) | 0.0107 (17) | 0.0106 (17) |
| C36 | 0.037 (2) | 0.0097 (17) | 0.028 (2) | 0.0013 (15) | 0.0110 (18) | 0.0065 (15) |
| N32 | 0.0300 (17) | 0.0149 (16) | 0.0235 (17) | 0.0049 (13) | 0.0133 (15) | 0.0039 (13) |
| O321 | 0.0219 (13) | 0.0217 (13) | 0.0265 (15) | 0.0044 (10) | 0.0044 (12) | 0.0057 (11) |
| O322 | 0.0294 (13) | 0.0155 (13) | 0.0348 (16) | −0.0002 (10) | 0.0107 (12) | 0.0009 (11) |
| N34 | 0.0213 (16) | 0.0269 (18) | 0.0275 (18) | 0.0019 (14) | 0.0058 (14) | 0.0114 (15) |
| O341 | 0.0224 (13) | 0.0229 (14) | 0.0389 (16) | −0.0030 (10) | 0.0045 (12) | 0.0094 (12) |
| O342 | 0.0241 (14) | 0.0340 (16) | 0.0488 (18) | 0.0085 (12) | 0.0119 (13) | 0.0168 (14) |
| N36 | 0.0272 (18) | 0.0194 (17) | 0.048 (2) | 0.0000 (14) | 0.0021 (17) | 0.0027 (16) |
| O361 | 0.022 (2) | 0.0260 (18) | 0.067 (6) | 0.003 (2) | 0.022 (3) | −0.006 (5) |
| O362 | 0.042 (4) | 0.019 (3) | 0.082 (6) | 0.005 (2) | 0.018 (4) | 0.015 (3) |
| O363 | 0.022 (2) | 0.0260 (18) | 0.067 (6) | 0.003 (2) | 0.022 (3) | −0.006 (5) |
| O364 | 0.019 (4) | 0.012 (3) | 0.059 (8) | 0.004 (3) | 0.001 (4) | 0.009 (4) |
| O011 | 0.0241 (13) | 0.0253 (13) | 0.0208 (14) | −0.0024 (10) | 0.0121 (11) | −0.0032 (11) |
| C011 | 0.0196 (18) | 0.026 (2) | 0.026 (2) | −0.0030 (15) | 0.0057 (16) | −0.0008 (17) |
| C012 | 0.061 (3) | 0.044 (3) | 0.047 (3) | −0.018 (2) | 0.012 (2) | 0.000 (2) |
| O021 | 0.0198 (12) | 0.0189 (12) | 0.0233 (14) | 0.0015 (9) | 0.0072 (11) | 0.0058 (10) |
| C021 | 0.029 (2) | 0.0134 (18) | 0.028 (2) | −0.0052 (14) | 0.0120 (17) | 0.0018 (15) |
| C022 | 0.034 (2) | 0.029 (2) | 0.041 (3) | −0.0041 (17) | 0.0141 (19) | 0.0195 (19) |
| O031 | 0.0402 (15) | 0.0219 (13) | 0.0164 (13) | 0.0101 (11) | 0.0107 (12) | 0.0039 (11) |
| C031 | 0.021 (3) | 0.032 (3) | 0.016 (3) | 0.007 (2) | 0.006 (2) | 0.000 (3) |
| C032 | 0.027 (3) | 0.032 (4) | 0.018 (4) | 0.001 (3) | −0.004 (3) | 0.005 (3) |
| O033 | 0.0402 (15) | 0.0219 (13) | 0.0164 (13) | 0.0101 (11) | 0.0107 (12) | 0.0039 (11) |
| C033 | 0.022 (6) | 0.030 (6) | 0.020 (6) | 0.020 (5) | 0.011 (5) | 0.006 (5) |
| C034 | 0.020 (6) | 0.069 (9) | 0.015 (6) | −0.006 (6) | −0.005 (5) | 0.006 (6) |
| N100 | 0.0185 (14) | 0.0234 (16) | 0.0115 (15) | −0.0043 (11) | 0.0037 (12) | 0.0028 (12) |
| N111 | 0.0232 (15) | 0.0219 (16) | 0.0180 (16) | 0.0032 (12) | 0.0089 (13) | 0.0056 (13) |
| C112 | 0.0284 (19) | 0.0150 (18) | 0.034 (2) | 0.0044 (14) | 0.0125 (18) | 0.0099 (16) |
| C113 | 0.0239 (19) | 0.034 (2) | 0.024 (2) | 0.0075 (15) | 0.0136 (16) | 0.0175 (17) |
| C114 | 0.030 (2) | 0.030 (2) | 0.018 (2) | 0.0013 (16) | 0.0102 (16) | 0.0059 (16) |
| C115 | 0.030 (2) | 0.0195 (19) | 0.023 (2) | 0.0024 (15) | 0.0090 (17) | 0.0034 (16) |
| C116 | 0.0206 (17) | 0.0169 (18) | 0.0161 (18) | 0.0019 (13) | 0.0069 (15) | 0.0044 (14) |
| N121 | 0.0236 (15) | 0.0234 (16) | 0.0195 (17) | 0.0019 (12) | 0.0081 (13) | 0.0058 (13) |
| C122 | 0.030 (2) | 0.029 (2) | 0.017 (2) | 0.0036 (16) | 0.0106 (17) | 0.0074 (16) |
| C123 | 0.029 (2) | 0.034 (2) | 0.019 (2) | −0.0006 (16) | 0.0022 (17) | 0.0055 (17) |
| C124 | 0.0208 (18) | 0.025 (2) | 0.032 (2) | 0.0013 (15) | 0.0029 (17) | 0.0080 (17) |
| C125 | 0.0225 (18) | 0.0203 (19) | 0.024 (2) | −0.0001 (14) | 0.0074 (16) | 0.0058 (16) |
| C126 | 0.0266 (18) | 0.0143 (17) | 0.0156 (19) | 0.0048 (14) | 0.0088 (15) | 0.0046 (14) |
| N131 | 0.0260 (16) | 0.0170 (15) | 0.0170 (16) | −0.0005 (12) | 0.0080 (13) | −0.0002 (12) |
| C132 | 0.038 (2) | 0.0204 (19) | 0.018 (2) | 0.0005 (16) | 0.0139 (17) | −0.0024 (15) |
| C133 | 0.035 (2) | 0.0207 (19) | 0.0158 (19) | −0.0013 (15) | 0.0100 (17) | 0.0013 (15) |
| C134 | 0.041 (2) | 0.0196 (19) | 0.024 (2) | 0.0007 (16) | 0.0181 (18) | 0.0082 (16) |
| C135 | 0.0276 (19) | 0.0223 (19) | 0.024 (2) | 0.0068 (15) | 0.0142 (16) | 0.0091 (16) |
| C136 | 0.0244 (18) | 0.0198 (18) | 0.0119 (18) | 0.0028 (14) | 0.0101 (15) | 0.0036 (14) |
| La2 | 0.01786 (10) | 0.01719 (11) | 0.01533 (11) | 0.00167 (8) | 0.00620 (9) | 0.00436 (8) |
| O41 | 0.0261 (13) | 0.0195 (13) | 0.0140 (13) | 0.0030 (10) | 0.0061 (10) | 0.0069 (10) |
| C41 | 0.0237 (19) | 0.027 (2) | 0.0170 (19) | 0.0020 (15) | 0.0061 (16) | 0.0117 (16) |
| C42 | 0.0155 (16) | 0.0200 (18) | 0.0132 (18) | 0.0021 (13) | 0.0010 (14) | 0.0057 (14) |
| C43 | 0.0212 (18) | 0.0185 (18) | 0.021 (2) | 0.0008 (14) | 0.0084 (15) | 0.0004 (15) |
| C44 | 0.0115 (16) | 0.0227 (19) | 0.026 (2) | 0.0031 (13) | 0.0033 (15) | 0.0081 (16) |
| C45 | 0.0245 (18) | 0.0219 (19) | 0.024 (2) | 0.0028 (14) | 0.0113 (16) | 0.0119 (16) |
| C46 | 0.0181 (17) | 0.0219 (19) | 0.0117 (18) | 0.0032 (14) | 0.0048 (14) | 0.0037 (14) |
| N42 | 0.0223 (15) | 0.0203 (16) | 0.0158 (16) | 0.0039 (12) | 0.0028 (13) | 0.0050 (13) |
| O421 | 0.0303 (13) | 0.0171 (13) | 0.0244 (14) | 0.0047 (10) | 0.0142 (11) | 0.0059 (11) |
| O422 | 0.0536 (17) | 0.0242 (14) | 0.0150 (14) | 0.0003 (12) | 0.0048 (13) | 0.0034 (12) |
| N44 | 0.0181 (15) | 0.0219 (17) | 0.0276 (19) | 0.0099 (12) | 0.0111 (14) | 0.0195 (15) |
| O441 | 0.0281 (14) | 0.0190 (14) | 0.052 (2) | 0.0045 (11) | 0.0117 (14) | 0.0090 (14) |
| O442 | 0.0356 (15) | 0.0219 (14) | 0.0414 (17) | 0.0079 (11) | 0.0186 (14) | 0.0142 (13) |
| N46 | 0.0283 (17) | 0.0257 (17) | 0.0257 (18) | 0.0071 (14) | 0.0062 (15) | 0.0155 (15) |
| O461 | 0.0443 (16) | 0.0310 (15) | 0.0212 (15) | −0.0067 (12) | 0.0075 (13) | 0.0053 (12) |
| O462 | 0.0447 (16) | 0.0469 (17) | 0.0263 (16) | 0.0057 (13) | 0.0215 (14) | 0.0098 (13) |
| O51 | 0.0227 (13) | 0.0273 (14) | 0.0172 (13) | 0.0091 (10) | 0.0092 (11) | 0.0074 (11) |
| C51 | 0.0253 (18) | 0.0133 (17) | 0.023 (2) | 0.0094 (14) | 0.0154 (16) | 0.0055 (15) |
| C52 | 0.0233 (19) | 0.025 (2) | 0.019 (2) | 0.0030 (15) | 0.0097 (16) | 0.0064 (16) |
| C53 | 0.036 (2) | 0.025 (2) | 0.0134 (19) | 0.0114 (16) | 0.0105 (16) | 0.0017 (15) |
| C54 | 0.042 (2) | 0.028 (2) | 0.020 (2) | 0.0139 (17) | 0.0205 (18) | 0.0130 (16) |
| C55 | 0.034 (2) | 0.029 (2) | 0.032 (2) | 0.0123 (16) | 0.0259 (19) | 0.0155 (17) |
| C56 | 0.0202 (18) | 0.0233 (19) | 0.030 (2) | 0.0120 (14) | 0.0131 (17) | 0.0092 (16) |
| N52 | 0.0325 (18) | 0.0217 (17) | 0.0200 (18) | 0.0098 (13) | 0.0082 (15) | 0.0054 (14) |
| O521 | 0.0253 (13) | 0.0298 (14) | 0.0162 (14) | 0.0016 (10) | 0.0101 (11) | 0.0030 (11) |
| O522 | 0.0377 (15) | 0.0375 (16) | 0.0178 (15) | −0.0060 (12) | 0.0000 (12) | −0.0020 (12) |
| N54 | 0.059 (2) | 0.038 (2) | 0.033 (2) | 0.0226 (18) | 0.033 (2) | 0.0180 (17) |
| O541 | 0.072 (2) | 0.072 (2) | 0.0190 (17) | 0.0246 (17) | 0.0168 (16) | 0.0239 (16) |
| O542 | 0.067 (2) | 0.060 (2) | 0.048 (2) | 0.0144 (16) | 0.0424 (17) | 0.0273 (16) |
| N56 | 0.0198 (16) | 0.042 (2) | 0.0283 (19) | 0.0070 (14) | 0.0143 (15) | 0.0080 (16) |
| O561 | 0.0278 (14) | 0.0454 (17) | 0.0285 (16) | 0.0096 (12) | 0.0090 (12) | 0.0137 (14) |
| O562 | 0.0331 (15) | 0.0415 (18) | 0.056 (2) | −0.0073 (13) | 0.0128 (14) | 0.0125 (15) |
| O61 | 0.0164 (12) | 0.0200 (13) | 0.0191 (13) | −0.0003 (9) | 0.0015 (10) | 0.0020 (10) |
| C61 | 0.029 (2) | 0.0175 (18) | 0.0067 (17) | 0.0013 (14) | 0.0067 (15) | 0.0016 (14) |
| C62 | 0.0248 (19) | 0.0228 (19) | 0.0176 (19) | −0.0008 (15) | 0.0112 (16) | 0.0053 (15) |
| C63 | 0.0270 (19) | 0.0178 (18) | 0.0156 (18) | 0.0046 (14) | 0.0095 (15) | 0.0045 (14) |
| C64 | 0.0130 (16) | 0.028 (2) | 0.0081 (17) | 0.0004 (14) | 0.0019 (13) | 0.0005 (14) |
| C65 | 0.0160 (17) | 0.0231 (19) | 0.0177 (19) | −0.0020 (14) | 0.0074 (15) | 0.0020 (15) |
| C66 | 0.0202 (18) | 0.0207 (19) | 0.0193 (19) | −0.0003 (14) | 0.0034 (15) | 0.0047 (15) |
| N62 | 0.0206 (16) | 0.0155 (15) | 0.0204 (16) | −0.0005 (12) | 0.0061 (13) | 0.0037 (13) |
| O621 | 0.0191 (13) | 0.0212 (13) | 0.0238 (14) | −0.0021 (10) | 0.0026 (11) | 0.0049 (11) |
| O622 | 0.0285 (14) | 0.0266 (14) | 0.0383 (16) | −0.0003 (11) | 0.0035 (12) | 0.0221 (13) |
| N64 | 0.0223 (16) | 0.0223 (17) | 0.0237 (18) | 0.0031 (13) | 0.0092 (14) | 0.0048 (14) |
| O641 | 0.0236 (13) | 0.0247 (14) | 0.0284 (15) | 0.0079 (10) | 0.0060 (11) | 0.0070 (12) |
| O642 | 0.0251 (13) | 0.0275 (14) | 0.0419 (17) | −0.0035 (11) | 0.0120 (12) | 0.0091 (12) |
| N66 | 0.0282 (17) | 0.0233 (17) | 0.036 (2) | 0.0043 (14) | 0.0143 (16) | 0.0140 (15) |
| O661 | 0.0201 (13) | 0.0354 (15) | 0.0474 (18) | 0.0043 (11) | 0.0024 (13) | 0.0239 (14) |
| O662 | 0.0396 (16) | 0.0194 (14) | 0.0534 (19) | −0.0042 (12) | 0.0088 (14) | 0.0108 (13) |
| O041 | 0.0208 (12) | 0.0295 (13) | 0.0157 (13) | 0.0053 (10) | 0.0078 (10) | 0.0096 (11) |
| C041 | 0.0136 (17) | 0.034 (2) | 0.025 (2) | −0.0005 (15) | 0.0003 (15) | 0.0138 (17) |
| C042 | 0.052 (3) | 0.046 (3) | 0.047 (3) | 0.031 (2) | 0.012 (2) | 0.018 (2) |
| O051 | 0.0216 (12) | 0.0121 (11) | 0.0206 (13) | 0.0007 (9) | 0.0084 (10) | −0.0027 (10) |
| C051 | 0.0234 (18) | 0.0171 (19) | 0.024 (2) | 0.0079 (14) | 0.0082 (16) | 0.0048 (15) |
| C052 | 0.035 (2) | 0.0184 (19) | 0.027 (2) | 0.0038 (15) | 0.0124 (18) | −0.0104 (16) |
| O061 | 0.0280 (13) | 0.0166 (12) | 0.0167 (13) | −0.0024 (9) | 0.0101 (11) | 0.0010 (10) |
| C061 | 0.031 (2) | 0.025 (2) | 0.0096 (18) | −0.0022 (15) | 0.0097 (16) | −0.0005 (15) |
| C062 | 0.027 (2) | 0.030 (2) | 0.022 (2) | 0.0034 (16) | 0.0104 (17) | 0.0019 (17) |
| N200 | 0.0221 (15) | 0.0206 (15) | 0.0164 (16) | 0.0046 (12) | 0.0094 (13) | 0.0045 (12) |
| N241 | 0.0189 (15) | 0.0159 (15) | 0.0224 (17) | 0.0032 (11) | 0.0097 (13) | 0.0041 (13) |
| C242 | 0.0175 (17) | 0.0177 (18) | 0.029 (2) | 0.0029 (14) | 0.0037 (16) | 0.0027 (16) |
| C243 | 0.0216 (18) | 0.023 (2) | 0.021 (2) | −0.0001 (14) | 0.0065 (16) | −0.0075 (16) |
| C244 | 0.0273 (19) | 0.029 (2) | 0.0150 (19) | −0.0016 (15) | 0.0105 (16) | 0.0055 (16) |
| C245 | 0.0270 (18) | 0.0154 (17) | 0.0163 (19) | −0.0013 (14) | 0.0087 (15) | 0.0008 (14) |
| C246 | 0.0198 (17) | 0.0177 (18) | 0.0171 (19) | 0.0016 (13) | 0.0050 (15) | −0.0002 (15) |
| N251 | 0.0269 (16) | 0.0219 (16) | 0.0163 (16) | 0.0029 (12) | 0.0106 (13) | 0.0012 (13) |
| C252 | 0.034 (2) | 0.0238 (19) | 0.0110 (18) | 0.0002 (15) | 0.0107 (16) | −0.0033 (15) |
| C253 | 0.037 (2) | 0.027 (2) | 0.0125 (19) | 0.0038 (16) | −0.0023 (17) | 0.0021 (16) |
| C254 | 0.0242 (19) | 0.026 (2) | 0.025 (2) | 0.0025 (15) | 0.0024 (17) | −0.0005 (17) |
| C255 | 0.0159 (17) | 0.030 (2) | 0.021 (2) | 0.0053 (14) | 0.0027 (15) | 0.0079 (16) |
| C256 | 0.0256 (18) | 0.0105 (17) | 0.0165 (19) | 0.0020 (13) | 0.0052 (15) | −0.0008 (14) |
| N261 | 0.0222 (15) | 0.0160 (15) | 0.0147 (15) | 0.0007 (11) | 0.0035 (13) | 0.0024 (12) |
| C262 | 0.0235 (19) | 0.027 (2) | 0.020 (2) | −0.0004 (15) | 0.0011 (16) | 0.0077 (16) |
| C263 | 0.029 (2) | 0.031 (2) | 0.028 (2) | 0.0119 (16) | 0.0104 (18) | 0.0156 (18) |
| C264 | 0.0279 (19) | 0.0153 (18) | 0.028 (2) | 0.0024 (14) | 0.0100 (17) | 0.0021 (16) |
| C265 | 0.0254 (18) | 0.0165 (18) | 0.0119 (18) | −0.0001 (14) | 0.0026 (15) | −0.0018 (14) |
| C266 | 0.0239 (18) | 0.0203 (18) | 0.0129 (18) | 0.0065 (14) | 0.0083 (15) | 0.0105 (14) |
| La1—O11 | 2.418 (2) | C134—C135 | 1.379 (4) |
| La1—O31 | 2.422 (2) | C134—H134 | 0.9500 |
| La1—O21 | 2.423 (2) | C135—C136 | 1.382 (4) |
| La1—O021 | 2.501 (2) | C135—H135 | 0.9500 |
| La1—O011 | 2.507 (2) | La2—O41 | 2.404 (2) |
| La1—O031 | 2.508 (2) | La2—O61 | 2.415 (2) |
| La1—O121 | 2.623 (2) | La2—O51 | 2.423 (2) |
| La1—O321 | 2.648 (2) | La2—O041 | 2.506 (2) |
| La1—O221 | 2.758 (2) | La2—O051 | 2.515 (2) |
| O11—C11 | 1.273 (3) | La2—O061 | 2.516 (2) |
| C11—C12 | 1.431 (4) | La2—O421 | 2.624 (2) |
| C11—C16 | 1.443 (4) | La2—O621 | 2.702 (2) |
| C12—C13 | 1.373 (4) | La2—O521 | 2.759 (2) |
| C12—N12 | 1.454 (4) | O41—C41 | 1.272 (4) |
| C13—C14 | 1.369 (4) | C41—C42 | 1.432 (4) |
| C13—H13 | 0.9500 | C41—C46 | 1.435 (4) |
| C14—C15 | 1.388 (5) | C42—C43 | 1.381 (4) |
| C14—N14 | 1.471 (4) | C42—N42 | 1.461 (4) |
| C15—C16 | 1.357 (4) | C43—C44 | 1.378 (4) |
| C15—H15 | 0.9500 | C43—H43 | 0.9500 |
| C16—N16 | 1.476 (4) | C44—C45 | 1.397 (5) |
| N12—O122 | 1.228 (4) | C44—N44 | 1.504 (4) |
| N12—O121 | 1.240 (3) | C45—C46 | 1.361 (4) |
| N14—O141 | 1.183 (4) | C45—H45 | 0.9500 |
| N14—O142 | 1.245 (4) | C46—N46 | 1.474 (4) |
| N16—O161 | 1.226 (3) | N42—O422 | 1.220 (3) |
| N16—O162 | 1.234 (3) | N42—O421 | 1.245 (3) |
| O21—C21 | 1.265 (4) | N44—O441 | 1.175 (3) |
| C21—C22 | 1.431 (5) | N44—O442 | 1.223 (3) |
| C21—C26 | 1.435 (5) | N46—O461 | 1.223 (3) |
| C22—C23 | 1.387 (4) | N46—O462 | 1.226 (3) |
| C22—N22 | 1.465 (4) | O51—C51 | 1.270 (4) |
| C23—C24 | 1.378 (5) | C51—C52 | 1.430 (5) |
| C23—H23 | 0.9500 | C51—C56 | 1.435 (4) |
| C24—C25 | 1.384 (5) | C52—C53 | 1.387 (4) |
| C24—N24 | 1.467 (4) | C52—N52 | 1.447 (4) |
| C25—C26 | 1.369 (5) | C53—C54 | 1.375 (5) |
| C25—H25 | 0.9500 | C53—H53 | 0.9500 |
| C26—N26 | 1.474 (5) | C54—C55 | 1.381 (5) |
| N22—O222 | 1.220 (4) | C54—N54 | 1.461 (4) |
| N22—O221 | 1.236 (3) | C55—C56 | 1.377 (4) |
| N24—O241 | 1.225 (4) | C55—H55 | 0.9500 |
| N24—O242 | 1.236 (4) | C56—N56 | 1.461 (4) |
| N26—O262 | 1.226 (4) | N52—O522 | 1.234 (3) |
| N26—O261 | 1.229 (4) | N52—O521 | 1.238 (3) |
| O31—C31 | 1.272 (4) | N54—O541 | 1.218 (4) |
| C31—C36 | 1.439 (5) | N54—O542 | 1.240 (4) |
| C31—C32 | 1.442 (4) | N56—O561 | 1.230 (4) |
| C32—C33 | 1.377 (4) | N56—O562 | 1.231 (4) |
| C32—N32 | 1.463 (4) | O61—C61 | 1.263 (4) |
| C33—C34 | 1.360 (4) | C61—C66 | 1.444 (4) |
| C33—H33 | 0.9500 | C61—C62 | 1.450 (5) |
| C34—C35 | 1.388 (4) | C62—C63 | 1.386 (4) |
| C34—N34 | 1.464 (4) | C62—N62 | 1.456 (4) |
| C35—C36 | 1.369 (5) | C63—C64 | 1.395 (4) |
| C35—H35 | 0.9500 | C63—H63 | 0.9500 |
| C36—N36 | 1.468 (4) | C64—C65 | 1.384 (4) |
| N32—O322 | 1.232 (3) | C64—N64 | 1.456 (4) |
| N32—O321 | 1.242 (3) | C65—C66 | 1.361 (4) |
| N34—O341 | 1.225 (3) | C65—H65 | 0.9500 |
| N34—O342 | 1.237 (3) | C66—N66 | 1.473 (4) |
| N36—O363 | 1.214 (12) | N62—O622 | 1.237 (3) |
| N36—O361 | 1.227 (9) | N62—O621 | 1.239 (3) |
| N36—O362 | 1.244 (7) | N64—O641 | 1.223 (3) |
| N36—O364 | 1.282 (9) | N64—O642 | 1.237 (3) |
| O011—C011 | 1.453 (4) | N66—O662 | 1.229 (3) |
| O011—H011 | 0.8400 | N66—O661 | 1.231 (3) |
| C011—C012 | 1.484 (5) | O041—C041 | 1.445 (4) |
| C011—H01A | 0.9900 | O041—H041 | 0.8400 |
| C011—H01B | 0.9900 | C041—C042 | 1.512 (5) |
| C012—H01C | 0.9800 | C041—H04A | 0.9900 |
| C012—H01D | 0.9800 | C041—H04B | 0.9900 |
| C012—H01E | 0.9800 | C042—H04C | 0.9800 |
| O021—C021 | 1.446 (3) | C042—H04D | 0.9800 |
| O021—H021 | 0.8400 | C042—H04E | 0.9800 |
| C021—C022 | 1.501 (5) | O051—C051 | 1.441 (4) |
| C021—H02A | 0.9900 | O051—H051 | 0.8402 |
| C021—H02B | 0.9900 | C051—C052 | 1.499 (4) |
| C022—H02C | 0.9800 | C051—H05A | 0.9900 |
| C022—H02D | 0.9800 | C051—H05B | 0.9900 |
| C022—H02E | 0.9800 | C052—H05C | 0.9800 |
| O031—C031 | 1.476 (6) | C052—H05D | 0.9800 |
| O031—H031 | 0.8396 | C052—H05E | 0.9800 |
| O031—H033 | 0.8393 | O061—C061 | 1.439 (4) |
| C031—C032 | 1.488 (7) | O061—H061 | 0.8401 |
| C031—H03A | 0.9900 | C061—C062 | 1.514 (4) |
| C031—H03B | 0.9900 | C061—H06A | 0.9900 |
| C032—H03C | 0.9800 | C061—H06B | 0.9900 |
| C032—H03D | 0.9800 | C062—H06C | 0.9800 |
| C032—H03E | 0.9800 | C062—H06D | 0.9800 |
| C033—C034 | 1.489 (12) | C062—H06E | 0.9800 |
| C033—H03F | 0.9900 | N200—C246 | 1.421 (4) |
| C033—H03G | 0.9900 | N200—C256 | 1.424 (4) |
| C034—H03H | 0.9800 | N200—C266 | 1.426 (4) |
| C034—H03I | 0.9800 | N241—C246 | 1.336 (4) |
| C034—H03J | 0.9800 | N241—C242 | 1.352 (4) |
| N100—C126 | 1.415 (4) | C242—C243 | 1.379 (5) |
| N100—C136 | 1.426 (4) | C242—H242 | 0.9500 |
| N100—C116 | 1.428 (4) | C243—C244 | 1.377 (5) |
| N111—C116 | 1.334 (4) | C243—H243 | 0.9500 |
| N111—C112 | 1.349 (4) | C244—C245 | 1.382 (4) |
| C112—C113 | 1.378 (5) | C244—H244 | 0.9500 |
| C112—H112 | 0.9500 | C245—C246 | 1.379 (4) |
| C113—C114 | 1.376 (5) | C245—H245 | 0.9500 |
| C113—H113 | 0.9500 | N251—C256 | 1.325 (4) |
| C114—C115 | 1.383 (4) | N251—C252 | 1.343 (4) |
| C114—H114 | 0.9500 | C252—C253 | 1.366 (5) |
| C115—C116 | 1.382 (4) | C252—H252 | 0.9500 |
| C115—H115 | 0.9500 | C253—C254 | 1.390 (5) |
| N121—C126 | 1.340 (4) | C253—H253 | 0.9500 |
| N121—C122 | 1.340 (4) | C254—C255 | 1.379 (5) |
| C122—C123 | 1.368 (5) | C254—H254 | 0.9500 |
| C122—H122 | 0.9500 | C255—C256 | 1.400 (4) |
| C123—C124 | 1.393 (5) | C255—H255 | 0.9500 |
| C123—H123 | 0.9500 | N261—C266 | 1.340 (4) |
| C124—C125 | 1.379 (5) | N261—C262 | 1.341 (4) |
| C124—H124 | 0.9500 | C262—C263 | 1.377 (5) |
| C125—C126 | 1.392 (4) | C262—H262 | 0.9500 |
| C125—H125 | 0.9500 | C263—C264 | 1.386 (5) |
| N131—C136 | 1.336 (4) | C263—H263 | 0.9500 |
| N131—C132 | 1.356 (4) | C264—C265 | 1.373 (4) |
| C132—C133 | 1.369 (5) | C264—H264 | 0.9500 |
| C132—H132 | 0.9500 | C265—C266 | 1.384 (4) |
| C133—C134 | 1.379 (5) | C265—H265 | 0.9500 |
| C133—H133 | 0.9500 | ||
| O11···O011 | 3.217 (3) | O41···O041 | 3.115 (4) |
| O21···O021 | 3.341 (3) | O51···O051 | 3.397 (4) |
| O31···O031 | 3.400 (4) | O61···O061 | 3.483 (4) |
| O11—La1—O31 | 83.56 (7) | C133—C134—H134 | 120.0 |
| O11—La1—O21 | 77.24 (7) | C134—C135—C136 | 117.7 (3) |
| O31—La1—O21 | 78.13 (8) | C134—C135—H135 | 121.2 |
| O11—La1—O021 | 135.75 (7) | C136—C135—H135 | 121.2 |
| O31—La1—O021 | 132.33 (7) | N131—C136—C135 | 123.7 (3) |
| O21—La1—O021 | 85.43 (7) | N131—C136—N100 | 115.6 (3) |
| O11—La1—O011 | 81.53 (7) | C135—C136—N100 | 120.6 (3) |
| O31—La1—O011 | 140.19 (7) | O41—La2—O61 | 84.07 (7) |
| O21—La1—O011 | 132.99 (7) | O41—La2—O51 | 78.16 (7) |
| O021—La1—O011 | 81.35 (7) | O61—La2—O51 | 79.12 (7) |
| O11—La1—O031 | 132.41 (7) | O41—La2—O041 | 78.73 (7) |
| O31—La1—O031 | 87.21 (8) | O61—La2—O041 | 139.58 (7) |
| O21—La1—O031 | 145.42 (7) | O51—La2—O041 | 131.15 (7) |
| O021—La1—O031 | 81.64 (7) | O41—La2—O051 | 136.73 (7) |
| O011—La1—O031 | 76.40 (7) | O61—La2—O051 | 132.83 (7) |
| O11—La1—O121 | 64.93 (7) | O51—La2—O051 | 86.93 (7) |
| O31—La1—O121 | 67.28 (7) | O041—La2—O051 | 81.41 (7) |
| O21—La1—O121 | 130.43 (7) | O41—La2—O061 | 132.65 (7) |
| O021—La1—O121 | 144.13 (7) | O61—La2—O061 | 89.85 (7) |
| O011—La1—O121 | 72.96 (7) | O51—La2—O061 | 146.34 (7) |
| O031—La1—O121 | 68.43 (7) | O041—La2—O061 | 76.13 (7) |
| O11—La1—O321 | 139.95 (7) | O051—La2—O061 | 77.46 (7) |
| O31—La1—O321 | 63.77 (7) | O41—La2—O421 | 65.29 (7) |
| O21—La1—O321 | 74.00 (7) | O61—La2—O421 | 66.78 (7) |
| O021—La1—O321 | 68.73 (7) | O51—La2—O421 | 131.44 (7) |
| O011—La1—O321 | 138.46 (7) | O041—La2—O421 | 72.81 (7) |
| O031—La1—O321 | 71.43 (7) | O051—La2—O421 | 141.63 (7) |
| O121—La1—O321 | 116.62 (7) | O061—La2—O421 | 69.19 (7) |
| O11—La1—O221 | 70.14 (7) | O41—La2—O621 | 139.50 (7) |
| O31—La1—O221 | 136.22 (7) | O61—La2—O621 | 62.92 (7) |
| O21—La1—O221 | 62.61 (7) | O51—La2—O621 | 73.33 (7) |
| O021—La1—O221 | 65.73 (7) | O041—La2—O621 | 141.71 (7) |
| O011—La1—O221 | 70.84 (7) | O051—La2—O621 | 69.92 (7) |
| O031—La1—O221 | 136.31 (7) | O061—La2—O621 | 73.33 (7) |
| O121—La1—O221 | 125.17 (7) | O421—La2—O621 | 115.75 (7) |
| O321—La1—O221 | 117.88 (7) | O41—La2—O521 | 71.61 (7) |
| C11—O11—La1 | 141.63 (19) | O61—La2—O521 | 137.79 (7) |
| O11—C11—C12 | 126.4 (3) | O51—La2—O521 | 62.72 (7) |
| O11—C11—C16 | 121.0 (3) | O041—La2—O521 | 69.31 (7) |
| C12—C11—C16 | 112.6 (3) | O051—La2—O521 | 65.47 (7) |
| C13—C12—C11 | 123.2 (3) | O061—La2—O521 | 131.97 (6) |
| C13—C12—N12 | 116.6 (3) | O421—La2—O521 | 126.73 (7) |
| C11—C12—N12 | 120.3 (3) | O621—La2—O521 | 117.28 (7) |
| C14—C13—C12 | 119.7 (3) | C41—O41—La2 | 142.7 (2) |
| C14—C13—H13 | 120.1 | O41—C41—C42 | 125.7 (3) |
| C12—C13—H13 | 120.1 | O41—C41—C46 | 120.9 (3) |
| C13—C14—C15 | 121.3 (3) | C42—C41—C46 | 113.4 (3) |
| C13—C14—N14 | 118.3 (3) | C43—C42—C41 | 123.1 (3) |
| C15—C14—N14 | 120.3 (3) | C43—C42—N42 | 115.6 (3) |
| C16—C15—C14 | 118.4 (3) | C41—C42—N42 | 121.3 (3) |
| C16—C15—H15 | 120.8 | C44—C43—C42 | 119.0 (3) |
| C14—C15—H15 | 120.8 | C44—C43—H43 | 120.5 |
| C15—C16—C11 | 124.7 (3) | C42—C43—H43 | 120.5 |
| C15—C16—N16 | 118.8 (3) | C43—C44—C45 | 121.7 (3) |
| C11—C16—N16 | 116.5 (3) | C43—C44—N44 | 118.2 (3) |
| O122—N12—O121 | 121.9 (3) | C45—C44—N44 | 120.1 (3) |
| O122—N12—C12 | 118.9 (3) | C46—C45—C44 | 118.0 (3) |
| O121—N12—C12 | 119.1 (3) | C46—C45—H45 | 121.0 |
| N12—O121—La1 | 133.32 (19) | C44—C45—H45 | 121.0 |
| O141—N14—O142 | 123.4 (3) | C45—C46—C41 | 124.6 (3) |
| O141—N14—C14 | 121.0 (3) | C45—C46—N46 | 118.9 (3) |
| O142—N14—C14 | 115.6 (3) | C41—C46—N46 | 116.4 (3) |
| O161—N16—O162 | 124.4 (3) | O422—N42—O421 | 121.8 (3) |
| O161—N16—C16 | 118.7 (3) | O422—N42—C42 | 119.2 (3) |
| O162—N16—C16 | 116.9 (3) | O421—N42—C42 | 118.9 (3) |
| C21—O21—La1 | 132.25 (19) | N42—O421—La2 | 135.20 (18) |
| O21—C21—C22 | 125.0 (3) | O441—N44—O442 | 128.1 (3) |
| O21—C21—C26 | 122.7 (3) | O441—N44—C44 | 117.6 (3) |
| C22—C21—C26 | 112.3 (3) | O442—N44—C44 | 114.2 (3) |
| C23—C22—C21 | 124.5 (3) | O461—N46—O462 | 125.2 (3) |
| C23—C22—N22 | 115.8 (3) | O461—N46—C46 | 117.6 (3) |
| C21—C22—N22 | 119.7 (3) | O462—N46—C46 | 117.2 (3) |
| C24—C23—C22 | 118.1 (3) | C51—O51—La2 | 133.24 (19) |
| C24—C23—H23 | 121.0 | O51—C51—C52 | 125.6 (3) |
| C22—C23—H23 | 121.0 | O51—C51—C56 | 121.5 (3) |
| C23—C24—C25 | 121.8 (3) | C52—C51—C56 | 112.9 (3) |
| C23—C24—N24 | 118.5 (4) | C53—C52—C51 | 123.9 (3) |
| C25—C24—N24 | 119.7 (4) | C53—C52—N52 | 116.7 (3) |
| C26—C25—C24 | 118.6 (3) | C51—C52—N52 | 119.4 (3) |
| C26—C25—H25 | 120.7 | C54—C53—C52 | 118.8 (3) |
| C24—C25—H25 | 120.7 | C54—C53—H53 | 120.6 |
| C25—C26—C21 | 124.6 (3) | C52—C53—H53 | 120.6 |
| C25—C26—N26 | 116.6 (3) | C53—C54—C55 | 121.4 (3) |
| C21—C26—N26 | 118.8 (3) | C53—C54—N54 | 118.8 (3) |
| O222—N22—O221 | 122.7 (3) | C55—C54—N54 | 119.7 (3) |
| O222—N22—C22 | 118.5 (3) | C56—C55—C54 | 119.0 (3) |
| O221—N22—C22 | 118.8 (3) | C56—C55—H55 | 120.5 |
| N22—O221—La1 | 137.2 (2) | C54—C55—H55 | 120.5 |
| O241—N24—O242 | 124.9 (4) | C55—C56—C51 | 123.8 (3) |
| O241—N24—C24 | 117.8 (4) | C55—C56—N56 | 117.8 (3) |
| O242—N24—C24 | 117.3 (4) | C51—C56—N56 | 118.2 (3) |
| O262—N26—O261 | 125.1 (3) | O522—N52—O521 | 122.1 (3) |
| O262—N26—C26 | 117.2 (3) | O522—N52—C52 | 118.0 (3) |
| O261—N26—C26 | 117.7 (3) | O521—N52—C52 | 119.9 (3) |
| C31—O31—La1 | 142.0 (2) | N52—O521—La2 | 136.9 (2) |
| O31—C31—C36 | 122.9 (3) | O541—N54—O542 | 124.1 (3) |
| O31—C31—C32 | 124.0 (3) | O541—N54—C54 | 118.5 (3) |
| C36—C31—C32 | 113.0 (3) | O542—N54—C54 | 117.3 (4) |
| C33—C32—C31 | 123.0 (3) | O561—N56—O562 | 123.6 (3) |
| C33—C32—N32 | 115.7 (3) | O561—N56—C56 | 118.7 (3) |
| C31—C32—N32 | 121.2 (3) | O562—N56—C56 | 117.6 (3) |
| C34—C33—C32 | 119.6 (3) | C61—O61—La2 | 141.8 (2) |
| C34—C33—H33 | 120.2 | O61—C61—C66 | 123.7 (3) |
| C32—C33—H33 | 120.2 | O61—C61—C62 | 124.1 (3) |
| C33—C34—C35 | 121.9 (3) | C66—C61—C62 | 112.0 (3) |
| C33—C34—N34 | 119.0 (3) | C63—C62—C61 | 124.2 (3) |
| C35—C34—N34 | 119.1 (3) | C63—C62—N62 | 115.4 (3) |
| C36—C35—C34 | 118.6 (3) | C61—C62—N62 | 120.4 (3) |
| C36—C35—H35 | 120.7 | C62—C63—C64 | 118.2 (3) |
| C34—C35—H35 | 120.7 | C62—C63—H63 | 120.9 |
| C35—C36—C31 | 123.9 (3) | C64—C63—H63 | 120.9 |
| C35—C36—N36 | 115.7 (3) | C65—C64—C63 | 121.6 (3) |
| C31—C36—N36 | 120.5 (3) | C65—C64—N64 | 119.4 (3) |
| O322—N32—O321 | 121.2 (3) | C63—C64—N64 | 119.0 (3) |
| O322—N32—C32 | 118.5 (3) | C66—C65—C64 | 119.1 (3) |
| O321—N32—C32 | 120.2 (3) | C66—C65—H65 | 120.4 |
| N32—O321—La1 | 142.00 (19) | C64—C65—H65 | 120.4 |
| O341—N34—O342 | 124.2 (3) | C65—C66—C61 | 124.9 (3) |
| O341—N34—C34 | 118.8 (3) | C65—C66—N66 | 116.8 (3) |
| O342—N34—C34 | 117.0 (3) | C61—C66—N66 | 118.3 (3) |
| O361—N36—O362 | 121.4 (12) | O622—N62—O621 | 121.7 (3) |
| O363—N36—O364 | 125.0 (16) | O622—N62—C62 | 118.1 (3) |
| O363—N36—C36 | 119.4 (17) | O621—N62—C62 | 120.3 (3) |
| O361—N36—C36 | 119.5 (12) | N62—O621—La2 | 140.69 (18) |
| O362—N36—C36 | 118.6 (4) | O641—N64—O642 | 123.7 (3) |
| O364—N36—C36 | 114.4 (5) | O641—N64—C64 | 119.0 (3) |
| C011—O011—La1 | 129.85 (18) | O642—N64—C64 | 117.3 (3) |
| C011—O011—H011 | 109.5 | O662—N66—O661 | 123.3 (3) |
| La1—O011—H011 | 120.5 | O662—N66—C66 | 117.0 (3) |
| O011—C011—C012 | 112.2 (3) | O661—N66—C66 | 119.6 (3) |
| O011—C011—H01A | 109.2 | C041—O041—La2 | 131.51 (17) |
| C012—C011—H01A | 109.2 | C041—O041—H041 | 109.5 |
| O011—C011—H01B | 109.2 | La2—O041—H041 | 118.6 |
| C012—C011—H01B | 109.2 | O041—C041—C042 | 112.2 (3) |
| H01A—C011—H01B | 107.9 | O041—C041—H04A | 109.2 |
| C011—C012—H01C | 109.5 | C042—C041—H04A | 109.2 |
| C011—C012—H01D | 109.5 | O041—C041—H04B | 109.2 |
| H01C—C012—H01D | 109.5 | C042—C041—H04B | 109.2 |
| C011—C012—H01E | 109.5 | H04A—C041—H04B | 107.9 |
| H01C—C012—H01E | 109.5 | C041—C042—H04C | 109.5 |
| H01D—C012—H01E | 109.5 | C041—C042—H04D | 109.5 |
| C021—O021—La1 | 127.51 (18) | H04C—C042—H04D | 109.5 |
| C021—O021—H021 | 109.5 | C041—C042—H04E | 109.5 |
| La1—O021—H021 | 119.5 | H04C—C042—H04E | 109.5 |
| O021—C021—C022 | 112.0 (3) | H04D—C042—H04E | 109.5 |
| O021—C021—H02A | 109.2 | C051—O051—La2 | 126.94 (17) |
| C022—C021—H02A | 109.2 | C051—O051—H051 | 109.5 |
| O021—C021—H02B | 109.2 | La2—O051—H051 | 118.4 |
| C022—C021—H02B | 109.2 | O051—C051—C052 | 111.7 (3) |
| H02A—C021—H02B | 107.9 | O051—C051—H05A | 109.3 |
| C021—C022—H02C | 109.5 | C052—C051—H05A | 109.3 |
| C021—C022—H02D | 109.5 | O051—C051—H05B | 109.3 |
| H02C—C022—H02D | 109.5 | C052—C051—H05B | 109.3 |
| C021—C022—H02E | 109.5 | H05A—C051—H05B | 107.9 |
| H02C—C022—H02E | 109.5 | C051—C052—H05C | 109.5 |
| H02D—C022—H02E | 109.5 | C051—C052—H05D | 109.5 |
| C031—O031—La1 | 138.2 (2) | H05C—C052—H05D | 109.5 |
| C031—O031—H031 | 109.4 | C051—C052—H05E | 109.5 |
| La1—O031—H031 | 109.9 | H05C—C052—H05E | 109.5 |
| C031—O031—H033 | 103.8 | H05D—C052—H05E | 109.5 |
| La1—O031—H033 | 117.8 | C061—O061—La2 | 135.52 (17) |
| O031—C031—C032 | 106.2 (4) | C061—O061—H061 | 109.5 |
| O031—C031—H03A | 110.5 | La2—O061—H061 | 113.9 |
| C032—C031—H03A | 110.5 | O061—C061—C062 | 110.5 (3) |
| O031—C031—H03B | 110.5 | O061—C061—H06A | 109.6 |
| C032—C031—H03B | 110.5 | C062—C061—H06A | 109.6 |
| H03A—C031—H03B | 108.7 | O061—C061—H06B | 109.5 |
| C031—C032—H03C | 109.5 | C062—C061—H06B | 109.5 |
| C031—C032—H03D | 109.5 | H06A—C061—H06B | 108.1 |
| H03C—C032—H03D | 109.5 | C061—C062—H06C | 109.5 |
| C031—C032—H03E | 109.5 | C061—C062—H06D | 109.5 |
| H03C—C032—H03E | 109.5 | H06C—C062—H06D | 109.5 |
| H03D—C032—H03E | 109.5 | C061—C062—H06E | 109.5 |
| C034—C033—H03F | 110.2 | H06C—C062—H06E | 109.5 |
| C034—C033—H03G | 110.2 | H06D—C062—H06E | 109.5 |
| H03F—C033—H03G | 108.5 | C246—N200—C256 | 120.8 (3) |
| C033—C034—H03H | 109.5 | C246—N200—C266 | 119.9 (3) |
| C033—C034—H03I | 109.5 | C256—N200—C266 | 118.8 (3) |
| H03H—C034—H03I | 109.5 | C246—N241—C242 | 117.3 (3) |
| C033—C034—H03J | 109.5 | N241—C242—C243 | 123.0 (3) |
| H03H—C034—H03J | 109.5 | N241—C242—H242 | 118.5 |
| H03I—C034—H03J | 109.5 | C243—C242—H242 | 118.5 |
| C126—N100—C136 | 119.9 (2) | C244—C243—C242 | 117.9 (3) |
| C126—N100—C116 | 120.2 (2) | C244—C243—H243 | 121.0 |
| C136—N100—C116 | 119.8 (3) | C242—C243—H243 | 121.0 |
| C116—N111—C112 | 116.8 (3) | C243—C244—C245 | 120.5 (3) |
| N111—C112—C113 | 123.4 (3) | C243—C244—H244 | 119.8 |
| N111—C112—H112 | 118.3 | C245—C244—H244 | 119.8 |
| C113—C112—H112 | 118.3 | C246—C245—C244 | 117.4 (3) |
| C114—C113—C112 | 118.6 (3) | C246—C245—H245 | 121.3 |
| C114—C113—H113 | 120.7 | C244—C245—H245 | 121.3 |
| C112—C113—H113 | 120.7 | N241—C246—C245 | 123.9 (3) |
| C113—C114—C115 | 119.2 (3) | N241—C246—N200 | 115.4 (3) |
| C113—C114—H114 | 120.4 | C245—C246—N200 | 120.7 (3) |
| C115—C114—H114 | 120.4 | C256—N251—C252 | 117.7 (3) |
| C114—C115—C116 | 118.3 (3) | N251—C252—C253 | 123.4 (3) |
| C114—C115—H115 | 120.9 | N251—C252—H252 | 118.3 |
| C116—C115—H115 | 120.9 | C253—C252—H252 | 118.3 |
| N111—C116—C115 | 123.7 (3) | C252—C253—C254 | 118.4 (3) |
| N111—C116—N100 | 115.1 (3) | C252—C253—H253 | 120.8 |
| C115—C116—N100 | 121.2 (3) | C254—C253—H253 | 120.8 |
| C126—N121—C122 | 117.8 (3) | C255—C254—C253 | 119.5 (3) |
| N121—C122—C123 | 123.6 (3) | C255—C254—H254 | 120.3 |
| N121—C122—H122 | 118.2 | C253—C254—H254 | 120.3 |
| C123—C122—H122 | 118.2 | C254—C255—C256 | 117.6 (3) |
| C122—C123—C124 | 118.5 (3) | C254—C255—H255 | 121.2 |
| C122—C123—H123 | 120.8 | C256—C255—H255 | 121.2 |
| C124—C123—H123 | 120.8 | N251—C256—C255 | 123.3 (3) |
| C125—C124—C123 | 118.9 (3) | N251—C256—N200 | 117.7 (3) |
| C125—C124—H124 | 120.5 | C255—C256—N200 | 119.0 (3) |
| C123—C124—H124 | 120.5 | C266—N261—C262 | 116.5 (3) |
| C124—C125—C126 | 118.7 (3) | N261—C262—C263 | 124.3 (3) |
| C124—C125—H125 | 120.6 | N261—C262—H262 | 117.9 |
| C126—C125—H125 | 120.6 | C263—C262—H262 | 117.9 |
| N121—C126—C125 | 122.4 (3) | C262—C263—C264 | 117.7 (3) |
| N121—C126—N100 | 116.5 (3) | C262—C263—H263 | 121.1 |
| C125—C126—N100 | 121.0 (3) | C264—C263—H263 | 121.1 |
| C136—N131—C132 | 117.0 (3) | C265—C264—C263 | 119.4 (3) |
| N131—C132—C133 | 123.2 (3) | C265—C264—H264 | 120.3 |
| N131—C132—H132 | 118.4 | C263—C264—H264 | 120.3 |
| C133—C132—H132 | 118.4 | C264—C265—C266 | 118.6 (3) |
| C132—C133—C134 | 118.3 (3) | C264—C265—H265 | 120.7 |
| C132—C133—H133 | 120.8 | C266—C265—H265 | 120.7 |
| C134—C133—H133 | 120.8 | N261—C266—C265 | 123.3 (3) |
| C135—C134—C133 | 120.1 (3) | N261—C266—N200 | 115.4 (3) |
| C135—C134—H134 | 120.0 | C265—C266—N200 | 121.3 (3) |
| N111—C116—N100—C126 | 42.2 (4) | N241—C246—N200—C256 | 41.8 (4) |
| N121—C126—N100—C136 | 38.1 (4) | N251—C256—N200—C266 | 36.9 (4) |
| N131—C136—N100—C116 | 40.1 (4) | N261—C266—N200—C246 | 34.0 (5) |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O011—H011···N111 | 0.839 | 1.902 | 2.740 (4) | 175 |
| O021—H021···N121 | 0.840 | 1.916 | 2.747 (3) | 170 |
| O031—H031···N131 | 0.840 | 1.895 | 2.693 (3) | 158 |
| O041—H041···N241i | 0.839 | 1.881 | 2.721 (4) | 179 |
| O051—H051···N251i | 0.841 | 1.934 | 2.769 (3) | 172 |
| O061—H061···N261i | 0.840 | 1.854 | 2.692 (4) | 175 |
| Symmetry codes: (i) x, y+1, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| O011—H011···N111 | 0.839 | 1.902 | 2.740 (4) | 175 |
| O021—H021···N121 | 0.840 | 1.916 | 2.747 (3) | 170 |
| O031—H031···N131 | 0.840 | 1.895 | 2.693 (3) | 158 |
| O041—H041···N241i | 0.839 | 1.881 | 2.721 (4) | 179 |
| O051—H051···N251i | 0.841 | 1.934 | 2.769 (3) | 172 |
| O061—H061···N261i | 0.840 | 1.854 | 2.692 (4) | 175 |
| Symmetry codes: (i) x, y+1, z. |
The author thanks Dr Brian Skelton, University of Western Australia Crystallography Centre, for assistance during the data collection and Professor Allan White, University of Western Australia School of Biomedical and Chemical Sciences, for supplying the starting materials.
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Hall, S. R., du Boulay, D. J. & Olthof-Hazekamp, R. (2001). The Xtal 3.7 System. The University of Western Australia, Australia.
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The title compound crystallizes in space group P1 with two independent groups of (C6H2N3O7-O,O')3La(O-C2H6O)3. (C5H4N)3N, (I), in the asymmetric unit (Z=4). Each individual bimolecular cluster comprises the metal-ligand adduct La(pic)3(EtOH)3 hydrogen bonded to the aromatic nitrogen base molecule tpa through a "face to face" arrangement in which the pyridine nitrogen atoms of the tpa molecules act as hydrogen bond acceptors and the hydroxy groups of ethanol ligands act as hydrogen bond donors (see Fig. 1 and Fig. 3). The primary coordination sphere of lanthanum is nine-coordinate, consisting only of ligand oxygen donor atoms, adopting the "fac" isomeric form of a tri-capped trigonal prism in which all three unidentate ethanol ligands occupy mutually "cis"-sites of one triangular face and the bidentate O,O'–picrate anions chelating through the phenoxy oxygen atoms at sites of the opposite triangular face and with an adjacent O–nitro oxygen atom at the capping site of each rectangular face (see Fig. 2).
The bimolecular cluster has a pseudo-threefold axis normal to the triangular faces of the tri-capped trigonal prism disposed about the lanthanum core. There is an obtuse (greater than 120°) nitro–O—La—O–nitro angle (approx. 125°) when compared with other angles associated with picrate nitro group oxygen atoms at the capping sites of the tri-capped trigonal prism (see Fig. 2, values for O121—La1—O321, O221 being 116.62 (7), 125.17 (7)° respectively with O321—La1—O221 being 117.88 (7)° and values for O421—La2—O621, O521 being 115.75 (7), 126.73 (7)° respectively with O621—La2—O521 being 117.28 (7)°). Presumably, the length of the corresponding rectangular edge (phenoxide oxygen and ethanol oxygen donor atoms) of the trigonal prism opposite to this angle becomes the shortest rectangular edge distance as a result of minimizing strain (contact distances for O11···O011, O21···O021 and O31···O031 being 3.217 (3), 3.341 (3) and 3.400 (4) Å respectively, with contact distances for O41···O041, O51···O051 and O61···O061 being 3.115 (4), 3.397 (4) and 3.483 (4) Å respectively). This observation exists concomitantly with a distortion of the inter-planar dihedral angle between the tpa pyridyl group, whose nitrogen atom is hydrogen bonded to the ethanol ligand which is associated with the above mentioned shorter rectangular edge, and the central NC3 plane of the tpa molecule. Noticeably, the dihedral angles between the NC3 and C5N planes of tpa which comprise nitrogen atoms labelled N111, N121 and N131 are 44.7 (1), 39.0 (1) and 40.0 (1)° respectively. The corresponding dihedral angles found in the second set of molecular coordinates for planes comprising nitrogen atoms N241, N251 and N261 are 45.7 (1), 40.6 (1) and 37.4 (1)° respectively. In agreement with the previous statement the angles for N111 and N241 are seen to be significantly larger.