Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270111030095/sq3293sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270111030095/sq3293Isup2.hkl |
CCDC reference: 846627
A mixture of La(NO3)3 (0.086 g, 0.2 mmol), PCA (0.137 mg, 0.6 mmol), phen (40 mg, 0.2 mmol), NaOH (0.240 g, 0.5 mol l-1) and EtOH/H2O (10 ml) was heated at 453 K for 50 h in a sealed 25 ml Teflon-lined stainless steel vessel under autogenous pressure. The reaction mixture was then cooled slowly to room temperature, whereupon colourless platelet single crystals of (I) were obtained in a yield of 55%. Spectroscopic analysis: IR (KBr, ν, cm-1): 3609 (ms), 3427 (m), 3077 (m), 3055 (m), 3020 (m), 2925 (m), 1953 (w), 1885 (w), 1808 (w), 1757 (w), 1635 (s), 1587 (sh), 1543 (sh), 1517 (s), 1490 (s), 1394 (sh), 1349 (s), 846 (m), 709 (s), 693 (s), 630 (m).
All H atoms bonded to C atoms were added at calculated positions and refined using a riding model, with C—H = 0.93 Å and Uiso = 1.2Ueq(C). The O-bound H atoms of the coordinated water and ethanol molecules could not be located reliably from the difference Fourier map; they have therefore been omitted from the refinement model but are included in the chemical formula and in all values derived from it. The displacement parameters indicated the presence of disorder, but a split-site model combined with restraints to the ADPs did not improve the model. We therefore adopted a dynamic disorder model with extremely strong restraints applied to the ADPs (ISOR and SIMU parameters of 0.004 Å2; Sheldrick, 2008).
Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[La2(C15H11O2)6(C12H8N2)2(C2H6O)(H2O)] | Z = 2 |
Mr = 2041.74 | F(000) = 2080 |
Triclinic, P1 | Dx = 1.387 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71075 Å |
a = 13.464 (3) Å | Cell parameters from 28884 reflections |
b = 18.572 (4) Å | θ = 3.0–27.4° |
c = 20.490 (4) Å | µ = 0.93 mm−1 |
α = 77.42 (3)° | T = 293 K |
β = 89.01 (3)° | Platelet, colourless |
γ = 77.94 (3)° | 0.38 × 0.27 × 0.10 mm |
V = 4887.9 (17) Å3 |
Rigaku R-AXIS RAPID diffractometer | 17208 independent reflections |
Radiation source: fine-focus sealed tube | 11202 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.056 |
Detector resolution: 14.6306 pixels mm-1 | θmax = 25.1°, θmin = 3.0° |
CCD profile fitting scans | h = −16→16 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −22→22 |
Tmin = 0.719, Tmax = 0.913 | l = −24→24 |
38229 measured reflections |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0596P)2 + 10.5654P] where P = (Fo2 + 2Fc2)/3 |
17208 reflections | (Δ/σ)max < 0.001 |
1226 parameters | Δρmax = 1.36 e Å−3 |
960 restraints | Δρmin = −1.22 e Å−3 |
[La2(C15H11O2)6(C12H8N2)2(C2H6O)(H2O)] | γ = 77.94 (3)° |
Mr = 2041.74 | V = 4887.9 (17) Å3 |
Triclinic, P1 | Z = 2 |
a = 13.464 (3) Å | Mo Kα radiation |
b = 18.572 (4) Å | µ = 0.93 mm−1 |
c = 20.490 (4) Å | T = 293 K |
α = 77.42 (3)° | 0.38 × 0.27 × 0.10 mm |
β = 89.01 (3)° |
Rigaku R-AXIS RAPID diffractometer | 17208 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 11202 reflections with I > 2σ(I) |
Tmin = 0.719, Tmax = 0.913 | Rint = 0.056 |
38229 measured reflections |
R[F2 > 2σ(F2)] = 0.059 | 960 restraints |
wR(F2) = 0.169 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0596P)2 + 10.5654P] where P = (Fo2 + 2Fc2)/3 |
17208 reflections | Δρmax = 1.36 e Å−3 |
1226 parameters | Δρmin = −1.22 e Å−3 |
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. |
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 > 2sigma(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 | ||
La1 | 0.15946 (3) | 0.21228 (2) | 0.34758 (2) | 0.03811 (13) | |
La2 | 0.24837 (3) | 0.35778 (2) | 0.166180 (19) | 0.03835 (13) | |
O1 | 0.0838 (4) | 0.2446 (3) | 0.5297 (3) | 0.0617 (15) | |
O2 | 0.2058 (4) | 0.1939 (3) | 0.4686 (2) | 0.0562 (13) | |
O3 | 0.0134 (4) | 0.2584 (3) | 0.2662 (2) | 0.0512 (12) | |
O4 | 0.0821 (4) | 0.3291 (3) | 0.1851 (3) | 0.0563 (12) | |
O5 | 0.2029 (4) | 0.1461 (3) | 0.2536 (3) | 0.0575 (13) | |
O6 | 0.2686 (5) | 0.2222 (3) | 0.1742 (3) | 0.0648 (14) | |
O7 | 0.1794 (4) | 0.3427 (3) | 0.3172 (3) | 0.0509 (12) | |
O8 | 0.2111 (4) | 0.4440 (3) | 0.2482 (2) | 0.0522 (12) | |
O9 | 0.3405 (4) | 0.2120 (3) | 0.3381 (2) | 0.0459 (11) | |
O10 | 0.3801 (4) | 0.2992 (3) | 0.2546 (2) | 0.0503 (12) | |
O11 | 0.2259 (4) | 0.3603 (3) | 0.0498 (3) | 0.0615 (14) | |
O12 | 0.1099 (6) | 0.4532 (4) | −0.0088 (3) | 0.093 (2) | |
O13 | 0.0121 (4) | 0.2778 (3) | 0.4081 (3) | 0.0657 (15) | |
O14 | 0.1177 (4) | 0.4814 (3) | 0.1120 (2) | 0.0539 (14) | |
N1 | 0.0371 (6) | 0.1111 (4) | 0.3809 (3) | 0.0586 (14) | |
N2 | 0.2423 (5) | 0.0635 (4) | 0.3986 (3) | 0.0546 (13) | |
N3 | 0.4358 (5) | 0.3203 (4) | 0.1101 (3) | 0.0610 (15) | |
N4 | 0.3683 (6) | 0.4611 (4) | 0.1308 (3) | 0.0591 (14) | |
C1 | 0.1666 (7) | 0.2023 (4) | 0.5235 (4) | 0.0503 (14) | |
C2 | 0.2214 (6) | 0.1551 (4) | 0.5873 (4) | 0.0509 (13) | |
C3 | 0.2959 (6) | 0.0957 (5) | 0.5841 (4) | 0.0549 (15) | |
H3 | 0.3132 | 0.0897 | 0.5412 | 0.066* | |
C4 | 0.3537 (7) | 0.0391 (5) | 0.6384 (5) | 0.0643 (15) | |
C5 | 0.3846 (7) | −0.0348 (5) | 0.6281 (5) | 0.0738 (18) | |
H5 | 0.3685 | −0.0457 | 0.5879 | 0.089* | |
C6 | 0.4392 (8) | −0.0916 (6) | 0.6784 (5) | 0.0833 (19) | |
H6 | 0.4568 | −0.1409 | 0.6727 | 0.100* | |
C7 | 0.4658 (8) | −0.0750 (6) | 0.7338 (6) | 0.087 (2) | |
H7 | 0.5053 | −0.1133 | 0.7656 | 0.104* | |
C8 | 0.4390 (8) | −0.0055 (6) | 0.7476 (6) | 0.0840 (19) | |
H8 | 0.4574 | 0.0030 | 0.7884 | 0.101* | |
C9 | 0.3823 (7) | 0.0538 (6) | 0.6983 (5) | 0.0746 (18) | |
H9 | 0.3643 | 0.1024 | 0.7059 | 0.090* | |
C10 | 0.1810 (7) | 0.1738 (5) | 0.6513 (4) | 0.0562 (14) | |
C11 | 0.1177 (7) | 0.1340 (5) | 0.6895 (4) | 0.0627 (16) | |
H11 | 0.0980 | 0.0951 | 0.6747 | 0.075* | |
C12 | 0.0822 (8) | 0.1500 (5) | 0.7493 (4) | 0.0706 (17) | |
H12 | 0.0375 | 0.1231 | 0.7734 | 0.085* | |
C13 | 0.1124 (8) | 0.2050 (5) | 0.7731 (5) | 0.0737 (17) | |
H13 | 0.0905 | 0.2147 | 0.8142 | 0.088* | |
C14 | 0.1755 (8) | 0.2459 (6) | 0.7360 (4) | 0.0740 (17) | |
H14 | 0.1952 | 0.2843 | 0.7517 | 0.089* | |
C15 | 0.2106 (8) | 0.2308 (5) | 0.6750 (4) | 0.0663 (16) | |
H15 | 0.2537 | 0.2588 | 0.6503 | 0.080* | |
C16 | −0.0675 (8) | 0.3395 (6) | 0.3921 (5) | 0.083 (2) | |
H16A | −0.0861 | 0.3478 | 0.3451 | 0.100* | |
H16B | −0.0449 | 0.3838 | 0.3986 | 0.100* | |
C17 | −0.1571 (10) | 0.3315 (8) | 0.4315 (7) | 0.122 (4) | |
H17A | −0.1637 | 0.2798 | 0.4406 | 0.183* | |
H17B | −0.2164 | 0.3630 | 0.4071 | 0.183* | |
H17C | −0.1503 | 0.3464 | 0.4730 | 0.183* | |
C18 | 0.0257 (6) | 0.2838 (4) | 0.2054 (4) | 0.0488 (13) | |
C19 | −0.0288 (6) | 0.2559 (4) | 0.1551 (4) | 0.0475 (13) | |
C20 | −0.0230 (6) | 0.2862 (5) | 0.0902 (4) | 0.0533 (14) | |
H20 | 0.0132 | 0.3246 | 0.0812 | 0.064* | |
C21 | −0.0641 (7) | 0.2694 (5) | 0.0307 (4) | 0.0618 (15) | |
C22 | −0.0753 (8) | 0.3230 (6) | −0.0283 (4) | 0.0735 (18) | |
H22 | −0.0587 | 0.3694 | −0.0291 | 0.088* | |
C23 | −0.1109 (8) | 0.3093 (6) | −0.0869 (5) | 0.0816 (19) | |
H23 | −0.1178 | 0.3464 | −0.1262 | 0.098* | |
C24 | −0.1355 (8) | 0.2420 (6) | −0.0868 (5) | 0.0818 (19) | |
H24 | −0.1610 | 0.2334 | −0.1256 | 0.098* | |
C25 | −0.1228 (8) | 0.1872 (6) | −0.0296 (4) | 0.0771 (18) | |
H25 | −0.1381 | 0.1408 | −0.0301 | 0.093* | |
C26 | −0.0872 (8) | 0.1994 (5) | 0.0298 (4) | 0.0695 (17) | |
H26 | −0.0789 | 0.1614 | 0.0685 | 0.083* | |
C27 | −0.0845 (6) | 0.1957 (4) | 0.1818 (4) | 0.0494 (13) | |
C28 | −0.1904 (7) | 0.2098 (5) | 0.1811 (4) | 0.0605 (16) | |
H28 | −0.2271 | 0.2589 | 0.1662 | 0.073* | |
C29 | −0.2416 (7) | 0.1523 (5) | 0.2022 (4) | 0.0691 (17) | |
H29 | −0.3123 | 0.1630 | 0.2010 | 0.083* | |
C30 | −0.1896 (7) | 0.0798 (5) | 0.2248 (4) | 0.0679 (17) | |
H30 | −0.2246 | 0.0411 | 0.2383 | 0.082* | |
C31 | −0.0843 (7) | 0.0641 (5) | 0.2274 (4) | 0.0650 (16) | |
H31 | −0.0483 | 0.0150 | 0.2432 | 0.078* | |
C32 | −0.0332 (7) | 0.1220 (5) | 0.2065 (4) | 0.0562 (15) | |
H32 | 0.0375 | 0.1112 | 0.2089 | 0.067* | |
C33 | 0.2390 (7) | 0.1621 (5) | 0.1972 (4) | 0.0580 (14) | |
C34 | 0.2484 (7) | 0.1058 (5) | 0.1531 (4) | 0.0624 (14) | |
C35 | 0.2577 (8) | 0.1303 (6) | 0.0876 (5) | 0.0790 (18) | |
H35 | 0.2520 | 0.1820 | 0.0730 | 0.095* | |
C36 | 0.2756 (10) | 0.0861 (7) | 0.0355 (6) | 0.0988 (19) | |
C37 | 0.2160 (11) | 0.1127 (8) | −0.0235 (7) | 0.117 (2) | |
H37 | 0.1676 | 0.1576 | −0.0305 | 0.140* | |
C38 | 0.2331 (12) | 0.0672 (8) | −0.0731 (7) | 0.129 (2) | |
H38 | 0.1923 | 0.0813 | −0.1119 | 0.154* | |
C39 | 0.3074 (12) | 0.0044 (8) | −0.0640 (8) | 0.129 (2) | |
H39 | 0.3220 | −0.0204 | −0.0989 | 0.155* | |
C40 | 0.3624 (11) | −0.0242 (8) | −0.0046 (7) | 0.122 (2) | |
H40 | 0.4077 | −0.0706 | 0.0033 | 0.146* | |
C41 | 0.3464 (10) | 0.0208 (7) | 0.0437 (6) | 0.109 (2) | |
H41 | 0.3862 | 0.0049 | 0.0829 | 0.130* | |
C42 | 0.2420 (8) | 0.0275 (5) | 0.1841 (5) | 0.0658 (15) | |
C43 | 0.1753 (8) | −0.0082 (5) | 0.1570 (5) | 0.0783 (18) | |
H43 | 0.1328 | 0.0176 | 0.1204 | 0.094* | |
C44 | 0.1743 (9) | −0.0842 (6) | 0.1867 (6) | 0.091 (2) | |
H44 | 0.1334 | −0.1098 | 0.1683 | 0.109* | |
C45 | 0.2308 (9) | −0.1182 (7) | 0.2399 (6) | 0.094 (2) | |
H45 | 0.2257 | −0.1675 | 0.2591 | 0.113* | |
C46 | 0.2968 (9) | −0.0881 (6) | 0.2698 (6) | 0.090 (2) | |
H46 | 0.3373 | −0.1156 | 0.3069 | 0.108* | |
C47 | 0.2996 (8) | −0.0119 (5) | 0.2405 (5) | 0.0754 (18) | |
H47 | 0.3414 | 0.0121 | 0.2599 | 0.090* | |
C48 | 0.3873 (6) | 0.2638 (4) | 0.3140 (4) | 0.0455 (12) | |
C49 | 0.4570 (6) | 0.2851 (4) | 0.3604 (4) | 0.0479 (13) | |
C50 | 0.4491 (6) | 0.2608 (4) | 0.4263 (4) | 0.0512 (14) | |
H50 | 0.4048 | 0.2281 | 0.4377 | 0.061* | |
C51 | 0.4972 (7) | 0.2762 (5) | 0.4842 (4) | 0.0584 (14) | |
C52 | 0.4551 (8) | 0.2549 (5) | 0.5457 (4) | 0.0684 (17) | |
H52 | 0.3992 | 0.2322 | 0.5482 | 0.082* | |
C53 | 0.4946 (8) | 0.2665 (6) | 0.6035 (5) | 0.0784 (18) | |
H53 | 0.4646 | 0.2523 | 0.6442 | 0.094* | |
C54 | 0.5769 (8) | 0.2986 (6) | 0.6014 (5) | 0.0794 (18) | |
H54 | 0.6034 | 0.3061 | 0.6403 | 0.095* | |
C55 | 0.6203 (8) | 0.3196 (6) | 0.5411 (5) | 0.0760 (18) | |
H55 | 0.6766 | 0.3416 | 0.5391 | 0.091* | |
C56 | 0.5801 (7) | 0.3082 (5) | 0.4827 (4) | 0.0665 (16) | |
H56 | 0.6103 | 0.3226 | 0.4422 | 0.080* | |
C57 | 0.5192 (7) | 0.3395 (5) | 0.3276 (4) | 0.0577 (14) | |
C58 | 0.6075 (8) | 0.3175 (6) | 0.2966 (5) | 0.0750 (17) | |
H58 | 0.6323 | 0.2666 | 0.2977 | 0.090* | |
C59 | 0.6613 (9) | 0.3714 (6) | 0.2629 (5) | 0.0835 (19) | |
H59 | 0.7214 | 0.3563 | 0.2419 | 0.100* | |
C60 | 0.6250 (9) | 0.4445 (6) | 0.2616 (5) | 0.0837 (19) | |
H60 | 0.6603 | 0.4798 | 0.2388 | 0.100* | |
C61 | 0.5421 (8) | 0.4679 (6) | 0.2912 (5) | 0.0829 (19) | |
H61 | 0.5189 | 0.5191 | 0.2894 | 0.099* | |
C62 | 0.4876 (8) | 0.4153 (5) | 0.3258 (5) | 0.0728 (17) | |
H62 | 0.4291 | 0.4320 | 0.3477 | 0.087* | |
C63 | 0.1950 (6) | 0.4092 (4) | 0.3058 (4) | 0.0473 (12) | |
C64 | 0.1972 (6) | 0.4479 (4) | 0.3635 (4) | 0.0466 (12) | |
C65 | 0.2124 (6) | 0.4033 (4) | 0.4255 (4) | 0.0527 (14) | |
H65 | 0.2112 | 0.3527 | 0.4293 | 0.063* | |
C66 | 0.2309 (8) | 0.4267 (5) | 0.4882 (4) | 0.0622 (15) | |
C67 | 0.1774 (8) | 0.4047 (5) | 0.5435 (4) | 0.0724 (17) | |
H67 | 0.1295 | 0.3758 | 0.5411 | 0.087* | |
C68 | 0.1935 (9) | 0.4248 (6) | 0.6036 (5) | 0.0825 (19) | |
H68 | 0.1530 | 0.4125 | 0.6398 | 0.099* | |
C69 | 0.2675 (9) | 0.4622 (6) | 0.6092 (5) | 0.0856 (19) | |
H69 | 0.2797 | 0.4742 | 0.6497 | 0.103* | |
C70 | 0.3252 (9) | 0.4826 (6) | 0.5543 (5) | 0.0837 (19) | |
H70 | 0.3773 | 0.5075 | 0.5579 | 0.100* | |
C71 | 0.3048 (8) | 0.4655 (5) | 0.4936 (5) | 0.0744 (18) | |
H71 | 0.3419 | 0.4808 | 0.4563 | 0.089* | |
C72 | 0.1821 (6) | 0.5310 (4) | 0.3499 (4) | 0.0480 (13) | |
C73 | 0.1060 (7) | 0.5709 (4) | 0.3821 (4) | 0.0556 (15) | |
H73 | 0.0665 | 0.5449 | 0.4124 | 0.067* | |
C74 | 0.0873 (7) | 0.6496 (5) | 0.3700 (4) | 0.0652 (17) | |
H74 | 0.0357 | 0.6759 | 0.3919 | 0.078* | |
C75 | 0.1453 (8) | 0.6874 (5) | 0.3259 (5) | 0.0694 (17) | |
H75 | 0.1332 | 0.7397 | 0.3181 | 0.083* | |
C76 | 0.2211 (7) | 0.6501 (5) | 0.2928 (4) | 0.0654 (16) | |
H76 | 0.2601 | 0.6767 | 0.2628 | 0.078* | |
C77 | 0.2393 (7) | 0.5711 (4) | 0.3048 (4) | 0.0556 (15) | |
H77 | 0.2904 | 0.5453 | 0.2822 | 0.067* | |
C78 | 0.1803 (7) | 0.3990 (5) | −0.0053 (4) | 0.0564 (15) | |
C79 | 0.2168 (6) | 0.3748 (5) | −0.0686 (4) | 0.0510 (13) | |
C80 | 0.1580 (6) | 0.4173 (5) | −0.1307 (4) | 0.0511 (13) | |
C81 | 0.1543 (6) | 0.4929 (5) | −0.1574 (4) | 0.0564 (15) | |
H81 | 0.1886 | 0.5197 | −0.1354 | 0.068* | |
C82 | 0.1005 (7) | 0.5292 (5) | −0.2162 (4) | 0.0645 (17) | |
H82 | 0.1003 | 0.5797 | −0.2339 | 0.077* | |
C83 | 0.0481 (7) | 0.4923 (6) | −0.2484 (4) | 0.0679 (17) | |
H83 | 0.0130 | 0.5174 | −0.2883 | 0.081* | |
C84 | 0.0461 (7) | 0.4178 (5) | −0.2226 (4) | 0.0652 (17) | |
H84 | 0.0078 | 0.3928 | −0.2437 | 0.078* | |
C85 | 0.1024 (6) | 0.3805 (5) | −0.1643 (4) | 0.0585 (16) | |
H85 | 0.1029 | 0.3297 | −0.1473 | 0.070* | |
C86 | 0.2981 (7) | 0.3190 (5) | −0.0653 (4) | 0.0570 (15) | |
H86 | 0.3206 | 0.2939 | −0.0221 | 0.068* | |
C87 | 0.3584 (8) | 0.2902 (5) | −0.1184 (4) | 0.0707 (16) | |
C88 | 0.3617 (8) | 0.3316 (6) | −0.1830 (4) | 0.0733 (18) | |
H88 | 0.3182 | 0.3785 | −0.1961 | 0.088* | |
C89 | 0.4283 (8) | 0.3045 (6) | −0.2288 (5) | 0.087 (2) | |
H89 | 0.4307 | 0.3337 | −0.2716 | 0.104* | |
C90 | 0.4903 (9) | 0.2348 (7) | −0.2105 (5) | 0.100 (2) | |
H90 | 0.5331 | 0.2160 | −0.2417 | 0.121* | |
C91 | 0.4905 (10) | 0.1927 (7) | −0.1475 (5) | 0.106 (2) | |
H91 | 0.5336 | 0.1454 | −0.1353 | 0.128* | |
C92 | 0.4253 (9) | 0.2213 (6) | −0.1013 (5) | 0.095 (2) | |
H92 | 0.4268 | 0.1930 | −0.0578 | 0.114* | |
C93 | 0.3346 (8) | 0.5313 (5) | 0.1406 (4) | 0.0682 (17) | |
H93 | 0.2708 | 0.5432 | 0.1585 | 0.082* | |
C94 | 0.3931 (8) | 0.5876 (6) | 0.1247 (5) | 0.0760 (18) | |
H94 | 0.3682 | 0.6359 | 0.1315 | 0.091* | |
C95 | 0.4848 (8) | 0.5693 (6) | 0.0998 (5) | 0.0768 (18) | |
H95 | 0.5237 | 0.6060 | 0.0896 | 0.092* | |
C96 | 0.5242 (8) | 0.4994 (6) | 0.0886 (4) | 0.0725 (16) | |
C97 | 0.6200 (8) | 0.4778 (7) | 0.0600 (5) | 0.0801 (19) | |
H97 | 0.6616 | 0.5126 | 0.0494 | 0.096* | |
C98 | 0.6503 (8) | 0.4114 (7) | 0.0485 (5) | 0.0831 (19) | |
H98 | 0.7127 | 0.4010 | 0.0286 | 0.100* | |
C99 | 0.5932 (7) | 0.3512 (7) | 0.0647 (5) | 0.0761 (16) | |
C100 | 0.6213 (8) | 0.2809 (7) | 0.0526 (5) | 0.0832 (19) | |
H100 | 0.6831 | 0.2676 | 0.0328 | 0.100* | |
C101 | 0.5623 (8) | 0.2304 (7) | 0.0685 (5) | 0.0791 (19) | |
H101 | 0.5829 | 0.1822 | 0.0603 | 0.095* | |
C102 | 0.4681 (7) | 0.2515 (6) | 0.0979 (4) | 0.0716 (18) | |
H102 | 0.4270 | 0.2163 | 0.1091 | 0.086* | |
C103 | 0.4972 (7) | 0.3705 (6) | 0.0932 (4) | 0.0637 (15) | |
C104 | 0.4621 (7) | 0.4439 (6) | 0.1053 (4) | 0.0627 (14) | |
C105 | −0.0622 (7) | 0.1338 (6) | 0.3728 (4) | 0.0662 (16) | |
H105 | −0.0883 | 0.1849 | 0.3561 | 0.079* | |
C106 | −0.1305 (8) | 0.0863 (6) | 0.3876 (4) | 0.0698 (17) | |
H106 | −0.2000 | 0.1054 | 0.3809 | 0.084* | |
C107 | −0.0942 (8) | 0.0122 (6) | 0.4117 (4) | 0.0688 (16) | |
H107 | −0.1391 | −0.0201 | 0.4233 | 0.083* | |
C108 | 0.0104 (8) | −0.0165 (5) | 0.4196 (4) | 0.0649 (14) | |
C109 | 0.0585 (8) | −0.0942 (5) | 0.4423 (5) | 0.0720 (17) | |
H109 | 0.0172 | −0.1293 | 0.4521 | 0.086* | |
C110 | 0.1562 (8) | −0.1190 (5) | 0.4500 (5) | 0.0727 (17) | |
H110 | 0.1827 | −0.1705 | 0.4642 | 0.087* | |
C111 | 0.2242 (8) | −0.0665 (5) | 0.4366 (5) | 0.0667 (15) | |
C112 | 0.3287 (8) | −0.0882 (5) | 0.4460 (5) | 0.0744 (18) | |
H112 | 0.3582 | −0.1388 | 0.4619 | 0.089* | |
C113 | 0.3889 (8) | −0.0369 (5) | 0.4324 (5) | 0.0724 (18) | |
H113 | 0.4591 | −0.0518 | 0.4385 | 0.087* | |
C114 | 0.3425 (7) | 0.0387 (5) | 0.4090 (4) | 0.0636 (16) | |
H114 | 0.3837 | 0.0739 | 0.4002 | 0.076* | |
C115 | 0.1836 (7) | 0.0105 (5) | 0.4136 (4) | 0.0563 (13) | |
C116 | 0.0757 (7) | 0.0361 (5) | 0.4041 (4) | 0.0573 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
La1 | 0.0424 (3) | 0.0410 (2) | 0.0372 (2) | −0.01891 (19) | 0.00661 (19) | −0.01270 (19) |
La2 | 0.0498 (3) | 0.0387 (2) | 0.0324 (2) | −0.0191 (2) | 0.00411 (19) | −0.01102 (18) |
O1 | 0.062 (3) | 0.072 (3) | 0.048 (3) | −0.001 (3) | 0.004 (3) | −0.019 (3) |
O2 | 0.066 (3) | 0.061 (3) | 0.044 (3) | −0.016 (3) | 0.009 (2) | −0.015 (2) |
O3 | 0.054 (3) | 0.056 (3) | 0.046 (2) | −0.016 (2) | −0.002 (2) | −0.013 (2) |
O4 | 0.050 (3) | 0.066 (3) | 0.062 (3) | −0.030 (2) | 0.002 (2) | −0.016 (2) |
O5 | 0.064 (3) | 0.058 (3) | 0.061 (3) | −0.019 (2) | 0.005 (3) | −0.031 (2) |
O6 | 0.078 (3) | 0.047 (3) | 0.077 (3) | −0.022 (3) | −0.005 (3) | −0.021 (3) |
O7 | 0.060 (3) | 0.043 (2) | 0.059 (3) | −0.022 (2) | 0.002 (2) | −0.021 (2) |
O8 | 0.071 (3) | 0.051 (3) | 0.043 (2) | −0.023 (2) | 0.005 (2) | −0.019 (2) |
O9 | 0.043 (3) | 0.051 (3) | 0.049 (2) | −0.019 (2) | 0.005 (2) | −0.013 (2) |
O10 | 0.049 (3) | 0.061 (3) | 0.042 (2) | −0.021 (2) | −0.004 (2) | −0.007 (2) |
O11 | 0.066 (3) | 0.075 (3) | 0.041 (3) | 0.000 (3) | 0.002 (2) | −0.020 (2) |
O12 | 0.099 (5) | 0.111 (5) | 0.050 (3) | 0.031 (4) | −0.001 (3) | −0.028 (3) |
O13 | 0.057 (3) | 0.079 (4) | 0.057 (3) | 0.004 (3) | 0.008 (3) | −0.023 (3) |
O14 | 0.069 (4) | 0.046 (3) | 0.044 (3) | −0.009 (3) | 0.001 (3) | −0.008 (2) |
N1 | 0.062 (3) | 0.070 (3) | 0.056 (3) | −0.038 (3) | 0.015 (3) | −0.016 (3) |
N2 | 0.066 (3) | 0.049 (3) | 0.053 (3) | −0.021 (3) | 0.020 (3) | −0.014 (2) |
N3 | 0.054 (3) | 0.082 (3) | 0.046 (3) | −0.011 (3) | −0.001 (2) | −0.014 (3) |
N4 | 0.070 (3) | 0.074 (3) | 0.043 (3) | −0.040 (3) | 0.003 (2) | −0.009 (3) |
C1 | 0.060 (3) | 0.053 (3) | 0.045 (3) | −0.021 (3) | 0.008 (3) | −0.017 (2) |
C2 | 0.060 (3) | 0.055 (3) | 0.046 (2) | −0.026 (2) | 0.007 (2) | −0.016 (2) |
C3 | 0.058 (3) | 0.059 (3) | 0.054 (3) | −0.022 (3) | 0.009 (3) | −0.017 (3) |
C4 | 0.059 (3) | 0.066 (3) | 0.067 (3) | −0.018 (3) | 0.008 (3) | −0.011 (3) |
C5 | 0.065 (3) | 0.072 (3) | 0.081 (3) | −0.016 (3) | 0.009 (3) | −0.007 (3) |
C6 | 0.073 (3) | 0.080 (3) | 0.090 (3) | −0.015 (3) | 0.008 (3) | −0.006 (3) |
C7 | 0.075 (3) | 0.087 (3) | 0.090 (3) | −0.015 (3) | 0.007 (3) | −0.003 (3) |
C8 | 0.075 (3) | 0.088 (3) | 0.082 (3) | −0.016 (3) | 0.003 (3) | −0.006 (3) |
C9 | 0.066 (3) | 0.078 (3) | 0.075 (3) | −0.014 (3) | 0.003 (3) | −0.008 (3) |
C10 | 0.071 (3) | 0.060 (3) | 0.048 (3) | −0.030 (3) | 0.011 (2) | −0.021 (2) |
C11 | 0.082 (4) | 0.067 (3) | 0.051 (3) | −0.034 (3) | 0.015 (3) | −0.021 (3) |
C12 | 0.092 (4) | 0.074 (3) | 0.056 (3) | −0.036 (3) | 0.020 (3) | −0.020 (3) |
C13 | 0.098 (4) | 0.078 (4) | 0.056 (3) | −0.033 (3) | 0.016 (3) | −0.026 (3) |
C14 | 0.096 (4) | 0.077 (3) | 0.062 (3) | −0.033 (3) | 0.013 (3) | −0.030 (3) |
C15 | 0.083 (4) | 0.070 (3) | 0.059 (3) | −0.035 (3) | 0.013 (3) | −0.025 (3) |
C16 | 0.076 (4) | 0.092 (4) | 0.073 (4) | −0.001 (4) | 0.007 (4) | −0.014 (4) |
C17 | 0.114 (5) | 0.122 (5) | 0.122 (5) | −0.014 (4) | 0.008 (4) | −0.019 (4) |
C18 | 0.048 (3) | 0.055 (3) | 0.047 (2) | −0.018 (2) | −0.001 (2) | −0.013 (2) |
C19 | 0.050 (3) | 0.053 (3) | 0.044 (2) | −0.019 (2) | 0.001 (2) | −0.013 (2) |
C20 | 0.061 (3) | 0.057 (3) | 0.047 (3) | −0.021 (3) | 0.003 (3) | −0.014 (3) |
C21 | 0.074 (3) | 0.067 (3) | 0.049 (3) | −0.024 (3) | 0.003 (3) | −0.014 (2) |
C22 | 0.087 (4) | 0.078 (3) | 0.055 (3) | −0.025 (3) | −0.001 (3) | −0.008 (3) |
C23 | 0.097 (4) | 0.088 (4) | 0.057 (3) | −0.023 (4) | −0.006 (3) | −0.007 (3) |
C24 | 0.100 (4) | 0.089 (4) | 0.058 (3) | −0.025 (4) | −0.008 (3) | −0.014 (3) |
C25 | 0.097 (4) | 0.080 (4) | 0.059 (3) | −0.027 (3) | −0.005 (3) | −0.018 (3) |
C26 | 0.087 (4) | 0.073 (3) | 0.053 (3) | −0.025 (3) | −0.001 (3) | −0.017 (3) |
C27 | 0.051 (3) | 0.056 (3) | 0.048 (3) | −0.025 (2) | 0.000 (2) | −0.012 (2) |
C28 | 0.056 (3) | 0.068 (3) | 0.060 (3) | −0.023 (3) | 0.000 (3) | −0.009 (3) |
C29 | 0.061 (3) | 0.079 (3) | 0.069 (3) | −0.028 (3) | 0.001 (3) | −0.006 (3) |
C30 | 0.068 (3) | 0.072 (3) | 0.068 (3) | −0.035 (3) | 0.000 (3) | −0.005 (3) |
C31 | 0.068 (3) | 0.064 (3) | 0.066 (3) | −0.028 (3) | 0.001 (3) | −0.006 (3) |
C32 | 0.058 (3) | 0.059 (3) | 0.057 (3) | −0.027 (3) | 0.001 (3) | −0.010 (3) |
C33 | 0.069 (3) | 0.050 (2) | 0.066 (3) | −0.020 (2) | 0.002 (3) | −0.028 (2) |
C34 | 0.075 (3) | 0.057 (3) | 0.067 (3) | −0.021 (3) | 0.007 (3) | −0.032 (2) |
C35 | 0.093 (3) | 0.074 (3) | 0.078 (3) | −0.019 (3) | 0.006 (3) | −0.031 (3) |
C36 | 0.109 (3) | 0.097 (3) | 0.093 (3) | −0.017 (2) | 0.002 (2) | −0.031 (2) |
C37 | 0.126 (3) | 0.115 (3) | 0.109 (3) | −0.015 (3) | −0.002 (3) | −0.032 (3) |
C38 | 0.136 (3) | 0.128 (3) | 0.118 (3) | −0.015 (3) | −0.002 (3) | −0.032 (3) |
C39 | 0.136 (3) | 0.128 (3) | 0.120 (3) | −0.015 (3) | 0.000 (3) | −0.033 (3) |
C40 | 0.129 (3) | 0.122 (3) | 0.113 (3) | −0.014 (3) | 0.003 (3) | −0.034 (3) |
C41 | 0.116 (3) | 0.110 (3) | 0.101 (3) | −0.015 (3) | 0.004 (3) | −0.034 (3) |
C42 | 0.078 (3) | 0.058 (3) | 0.074 (3) | −0.025 (3) | 0.014 (3) | −0.032 (3) |
C43 | 0.087 (3) | 0.070 (3) | 0.089 (3) | −0.028 (3) | 0.011 (3) | −0.031 (3) |
C44 | 0.095 (3) | 0.083 (3) | 0.100 (3) | −0.027 (3) | 0.010 (3) | −0.026 (3) |
C45 | 0.099 (3) | 0.085 (3) | 0.099 (3) | −0.024 (3) | 0.014 (3) | −0.017 (3) |
C46 | 0.097 (3) | 0.082 (3) | 0.090 (3) | −0.017 (3) | 0.014 (3) | −0.018 (3) |
C47 | 0.088 (3) | 0.065 (3) | 0.078 (3) | −0.019 (3) | 0.019 (3) | −0.024 (3) |
C48 | 0.045 (3) | 0.052 (3) | 0.043 (2) | −0.017 (2) | 0.003 (2) | −0.013 (2) |
C49 | 0.051 (3) | 0.055 (3) | 0.045 (2) | −0.021 (2) | 0.005 (2) | −0.017 (2) |
C50 | 0.055 (3) | 0.059 (3) | 0.046 (3) | −0.023 (3) | 0.005 (3) | −0.014 (3) |
C51 | 0.064 (3) | 0.070 (3) | 0.048 (3) | −0.028 (3) | −0.001 (3) | −0.014 (2) |
C52 | 0.073 (3) | 0.084 (3) | 0.053 (3) | −0.028 (3) | −0.002 (3) | −0.015 (3) |
C53 | 0.082 (3) | 0.093 (3) | 0.063 (3) | −0.025 (3) | −0.002 (3) | −0.017 (3) |
C54 | 0.086 (4) | 0.096 (4) | 0.062 (3) | −0.031 (3) | −0.012 (3) | −0.018 (3) |
C55 | 0.082 (4) | 0.090 (4) | 0.063 (3) | −0.035 (3) | −0.012 (3) | −0.014 (3) |
C56 | 0.072 (3) | 0.080 (3) | 0.054 (3) | −0.032 (3) | −0.006 (3) | −0.011 (3) |
C57 | 0.059 (3) | 0.064 (3) | 0.060 (3) | −0.029 (2) | 0.005 (2) | −0.020 (2) |
C58 | 0.075 (3) | 0.077 (3) | 0.078 (3) | −0.029 (2) | 0.011 (2) | −0.019 (2) |
C59 | 0.083 (3) | 0.088 (3) | 0.084 (3) | −0.031 (3) | 0.014 (3) | −0.018 (3) |
C60 | 0.086 (3) | 0.086 (3) | 0.085 (3) | −0.038 (3) | 0.007 (3) | −0.011 (3) |
C61 | 0.082 (3) | 0.081 (3) | 0.088 (3) | −0.031 (3) | 0.000 (3) | −0.009 (3) |
C62 | 0.070 (3) | 0.073 (3) | 0.079 (3) | −0.031 (3) | 0.002 (3) | −0.009 (3) |
C63 | 0.060 (3) | 0.046 (2) | 0.046 (2) | −0.023 (2) | 0.003 (2) | −0.019 (2) |
C64 | 0.060 (3) | 0.045 (2) | 0.044 (2) | −0.024 (2) | 0.005 (2) | −0.016 (2) |
C65 | 0.071 (3) | 0.050 (3) | 0.046 (3) | −0.026 (3) | 0.004 (3) | −0.016 (2) |
C66 | 0.086 (3) | 0.059 (3) | 0.049 (3) | −0.027 (3) | 0.003 (3) | −0.017 (2) |
C67 | 0.097 (4) | 0.072 (3) | 0.056 (3) | −0.029 (3) | 0.002 (3) | −0.020 (3) |
C68 | 0.100 (3) | 0.084 (3) | 0.068 (3) | −0.026 (3) | 0.002 (3) | −0.020 (3) |
C69 | 0.110 (4) | 0.086 (4) | 0.066 (3) | −0.029 (3) | −0.006 (3) | −0.021 (3) |
C70 | 0.107 (4) | 0.082 (4) | 0.068 (3) | −0.030 (3) | −0.008 (3) | −0.019 (3) |
C71 | 0.097 (4) | 0.074 (3) | 0.058 (3) | −0.028 (3) | −0.002 (3) | −0.018 (3) |
C72 | 0.061 (3) | 0.043 (2) | 0.047 (3) | −0.017 (2) | −0.002 (2) | −0.018 (2) |
C73 | 0.067 (3) | 0.047 (3) | 0.056 (3) | −0.009 (3) | −0.001 (3) | −0.020 (3) |
C74 | 0.076 (4) | 0.053 (3) | 0.067 (3) | −0.007 (3) | −0.004 (3) | −0.020 (3) |
C75 | 0.083 (4) | 0.051 (3) | 0.074 (4) | −0.012 (3) | −0.009 (3) | −0.013 (3) |
C76 | 0.079 (4) | 0.052 (3) | 0.067 (3) | −0.020 (3) | −0.006 (3) | −0.010 (3) |
C77 | 0.070 (3) | 0.046 (3) | 0.055 (3) | −0.018 (3) | −0.002 (3) | −0.015 (3) |
C78 | 0.061 (3) | 0.071 (3) | 0.036 (3) | −0.006 (3) | 0.000 (3) | −0.017 (3) |
C79 | 0.058 (3) | 0.063 (3) | 0.035 (2) | −0.014 (2) | 0.001 (2) | −0.016 (2) |
C80 | 0.055 (3) | 0.063 (3) | 0.037 (2) | −0.013 (2) | −0.001 (2) | −0.013 (2) |
C81 | 0.060 (3) | 0.065 (3) | 0.044 (3) | −0.015 (3) | −0.004 (3) | −0.010 (3) |
C82 | 0.064 (3) | 0.072 (3) | 0.051 (3) | −0.010 (3) | −0.003 (3) | −0.004 (3) |
C83 | 0.064 (3) | 0.083 (4) | 0.050 (3) | −0.009 (3) | −0.007 (3) | −0.006 (3) |
C84 | 0.064 (3) | 0.081 (3) | 0.051 (3) | −0.015 (3) | −0.011 (3) | −0.013 (3) |
C85 | 0.061 (3) | 0.070 (3) | 0.046 (3) | −0.015 (3) | −0.008 (3) | −0.013 (3) |
C86 | 0.068 (3) | 0.065 (3) | 0.037 (3) | −0.007 (3) | −0.001 (3) | −0.017 (3) |
C87 | 0.082 (3) | 0.075 (3) | 0.048 (3) | 0.007 (3) | 0.001 (3) | −0.020 (3) |
C88 | 0.084 (4) | 0.080 (4) | 0.049 (3) | 0.006 (3) | 0.003 (3) | −0.020 (3) |
C89 | 0.097 (4) | 0.094 (4) | 0.056 (3) | 0.014 (4) | 0.007 (3) | −0.020 (3) |
C90 | 0.110 (4) | 0.104 (4) | 0.065 (3) | 0.026 (4) | 0.010 (4) | −0.018 (4) |
C91 | 0.117 (4) | 0.104 (4) | 0.071 (4) | 0.032 (4) | 0.008 (4) | −0.014 (4) |
C92 | 0.106 (4) | 0.094 (4) | 0.063 (3) | 0.025 (4) | 0.005 (3) | −0.014 (3) |
C93 | 0.085 (4) | 0.074 (3) | 0.055 (3) | −0.042 (3) | 0.002 (3) | −0.011 (3) |
C94 | 0.092 (4) | 0.082 (4) | 0.063 (3) | −0.046 (3) | −0.004 (3) | −0.009 (3) |
C95 | 0.084 (4) | 0.093 (4) | 0.063 (3) | −0.050 (3) | −0.009 (3) | −0.005 (3) |
C96 | 0.070 (3) | 0.099 (3) | 0.053 (3) | −0.044 (3) | −0.005 (3) | −0.002 (3) |
C97 | 0.066 (3) | 0.115 (4) | 0.061 (3) | −0.042 (3) | −0.009 (3) | 0.001 (3) |
C98 | 0.061 (3) | 0.121 (4) | 0.062 (3) | −0.027 (3) | −0.005 (3) | 0.000 (3) |
C99 | 0.059 (3) | 0.110 (3) | 0.054 (3) | −0.017 (3) | −0.004 (3) | −0.006 (3) |
C100 | 0.065 (4) | 0.112 (4) | 0.062 (3) | −0.004 (3) | −0.002 (3) | −0.010 (3) |
C101 | 0.068 (4) | 0.101 (4) | 0.060 (3) | 0.000 (3) | −0.002 (3) | −0.015 (3) |
C102 | 0.062 (3) | 0.090 (4) | 0.057 (3) | −0.003 (3) | 0.000 (3) | −0.015 (3) |
C103 | 0.054 (3) | 0.093 (3) | 0.044 (3) | −0.021 (3) | −0.003 (2) | −0.008 (3) |
C104 | 0.062 (3) | 0.088 (3) | 0.044 (2) | −0.037 (3) | −0.002 (2) | −0.007 (3) |
C105 | 0.064 (3) | 0.082 (3) | 0.064 (3) | −0.041 (3) | 0.013 (3) | −0.016 (3) |
C106 | 0.068 (3) | 0.090 (3) | 0.066 (3) | −0.046 (3) | 0.011 (3) | −0.020 (3) |
C107 | 0.074 (3) | 0.087 (3) | 0.063 (3) | −0.052 (3) | 0.013 (3) | −0.021 (3) |
C108 | 0.081 (3) | 0.071 (3) | 0.058 (3) | −0.046 (3) | 0.013 (3) | −0.020 (3) |
C109 | 0.092 (4) | 0.067 (3) | 0.069 (3) | −0.045 (3) | 0.012 (3) | −0.014 (3) |
C110 | 0.094 (4) | 0.059 (3) | 0.072 (3) | −0.034 (3) | 0.011 (3) | −0.012 (3) |
C111 | 0.086 (3) | 0.054 (3) | 0.066 (3) | −0.028 (3) | 0.015 (3) | −0.011 (3) |
C112 | 0.088 (4) | 0.056 (3) | 0.074 (3) | −0.015 (3) | 0.014 (3) | −0.006 (3) |
C113 | 0.080 (4) | 0.057 (3) | 0.074 (3) | −0.012 (3) | 0.017 (3) | −0.004 (3) |
C114 | 0.071 (3) | 0.052 (3) | 0.067 (3) | −0.018 (3) | 0.016 (3) | −0.008 (3) |
C115 | 0.074 (3) | 0.051 (2) | 0.052 (3) | −0.028 (2) | 0.017 (3) | −0.016 (2) |
C116 | 0.071 (3) | 0.062 (3) | 0.051 (3) | −0.039 (3) | 0.015 (2) | −0.018 (2) |
La1—O7 | 2.436 (5) | C47—H47 | 0.9300 |
La1—O9 | 2.440 (5) | C48—C49 | 1.514 (10) |
La1—O3 | 2.483 (5) | C49—C50 | 1.339 (10) |
La1—O2 | 2.499 (5) | C49—C57 | 1.487 (11) |
La1—O5 | 2.500 (5) | C50—C51 | 1.469 (11) |
La1—O13 | 2.553 (5) | C50—H50 | 0.9300 |
La1—N1 | 2.722 (7) | C51—C56 | 1.368 (12) |
La1—N2 | 2.733 (7) | C51—C52 | 1.385 (11) |
La2—O11 | 2.398 (5) | C52—C53 | 1.384 (12) |
La2—O4 | 2.413 (5) | C52—H52 | 0.9300 |
La2—O6 | 2.445 (5) | C53—C54 | 1.358 (14) |
La2—O10 | 2.462 (5) | C53—H53 | 0.9300 |
La2—O8 | 2.539 (5) | C54—C55 | 1.372 (13) |
La2—O14 | 2.620 (5) | C54—H54 | 0.9300 |
La2—N4 | 2.732 (7) | C55—C56 | 1.395 (12) |
La2—N3 | 2.772 (7) | C55—H55 | 0.9300 |
O1—C1 | 1.244 (9) | C56—H56 | 0.9300 |
O2—C1 | 1.261 (8) | C57—C58 | 1.367 (12) |
O3—C18 | 1.255 (9) | C57—C62 | 1.375 (12) |
O4—C18 | 1.249 (9) | C58—C59 | 1.410 (13) |
O5—C33 | 1.246 (10) | C58—H58 | 0.9300 |
O6—C33 | 1.256 (10) | C59—C60 | 1.338 (14) |
O7—C63 | 1.268 (8) | C59—H59 | 0.9300 |
O8—C63 | 1.255 (9) | C60—C61 | 1.300 (14) |
O9—C48 | 1.267 (9) | C60—H60 | 0.9300 |
O10—C48 | 1.244 (9) | C61—C62 | 1.405 (13) |
O11—C78 | 1.285 (9) | C61—H61 | 0.9300 |
O12—C78 | 1.222 (10) | C62—H62 | 0.9300 |
O13—C16 | 1.381 (11) | C63—C64 | 1.514 (9) |
N1—C105 | 1.317 (11) | C64—C65 | 1.350 (10) |
N1—C116 | 1.362 (11) | C64—C72 | 1.478 (10) |
N2—C114 | 1.337 (11) | C65—C66 | 1.483 (10) |
N2—C115 | 1.368 (10) | C65—H65 | 0.9300 |
N3—C102 | 1.339 (11) | C66—C71 | 1.364 (13) |
N3—C103 | 1.357 (11) | C66—C67 | 1.365 (12) |
N4—C93 | 1.346 (11) | C67—C68 | 1.394 (12) |
N4—C104 | 1.359 (11) | C67—H67 | 0.9300 |
C1—C2 | 1.512 (11) | C68—C69 | 1.347 (14) |
C2—C3 | 1.339 (11) | C68—H68 | 0.9300 |
C2—C10 | 1.493 (10) | C69—C70 | 1.386 (14) |
C3—C4 | 1.458 (12) | C69—H69 | 0.9300 |
C3—H3 | 0.9300 | C70—C71 | 1.394 (12) |
C4—C9 | 1.392 (13) | C70—H70 | 0.9300 |
C4—C5 | 1.410 (12) | C71—H71 | 0.9300 |
C5—C6 | 1.393 (13) | C72—C73 | 1.381 (11) |
C5—H5 | 0.9300 | C72—C77 | 1.384 (11) |
C6—C7 | 1.314 (14) | C73—C74 | 1.398 (11) |
C6—H6 | 0.9300 | C73—H73 | 0.9300 |
C7—C8 | 1.355 (14) | C74—C75 | 1.359 (13) |
C7—H7 | 0.9300 | C74—H74 | 0.9300 |
C8—C9 | 1.417 (13) | C75—C76 | 1.365 (12) |
C8—H8 | 0.9300 | C75—H75 | 0.9300 |
C9—H9 | 0.9300 | C76—C77 | 1.403 (11) |
C10—C11 | 1.370 (11) | C76—H76 | 0.9300 |
C10—C15 | 1.386 (11) | C77—H77 | 0.9300 |
C11—C12 | 1.376 (11) | C78—C79 | 1.505 (10) |
C11—H11 | 0.9300 | C79—C86 | 1.332 (11) |
C12—C13 | 1.357 (12) | C79—C80 | 1.484 (11) |
C12—H12 | 0.9300 | C80—C81 | 1.382 (11) |
C13—C14 | 1.369 (13) | C80—C85 | 1.392 (11) |
C13—H13 | 0.9300 | C81—C82 | 1.380 (11) |
C14—C15 | 1.394 (11) | C81—H81 | 0.9300 |
C14—H14 | 0.9300 | C82—C83 | 1.347 (12) |
C15—H15 | 0.9300 | C82—H82 | 0.9300 |
C16—C17 | 1.456 (15) | C83—C84 | 1.375 (12) |
C16—H16A | 0.9700 | C83—H83 | 0.9300 |
C16—H16B | 0.9700 | C84—C85 | 1.390 (11) |
C17—H17A | 0.9600 | C84—H84 | 0.9300 |
C17—H17B | 0.9600 | C85—H85 | 0.9300 |
C17—H17C | 0.9600 | C86—C87 | 1.473 (11) |
C18—C19 | 1.512 (10) | C86—H86 | 0.9300 |
C19—C20 | 1.334 (10) | C87—C92 | 1.381 (13) |
C19—C27 | 1.478 (10) | C87—C88 | 1.385 (12) |
C20—C21 | 1.466 (11) | C88—C89 | 1.387 (12) |
C20—H20 | 0.9300 | C88—H88 | 0.9300 |
C21—C22 | 1.378 (12) | C89—C90 | 1.363 (13) |
C21—C26 | 1.403 (12) | C89—H89 | 0.9300 |
C22—C23 | 1.391 (13) | C90—C91 | 1.356 (14) |
C22—H22 | 0.9300 | C90—H90 | 0.9300 |
C23—C24 | 1.359 (14) | C91—C92 | 1.394 (13) |
C23—H23 | 0.9300 | C91—H91 | 0.9300 |
C24—C25 | 1.361 (13) | C92—H92 | 0.9300 |
C24—H24 | 0.9300 | C93—C94 | 1.416 (12) |
C25—C26 | 1.396 (12) | C93—H93 | 0.9300 |
C25—H25 | 0.9300 | C94—C95 | 1.334 (14) |
C26—H26 | 0.9300 | C94—H94 | 0.9300 |
C27—C32 | 1.386 (11) | C95—C96 | 1.362 (14) |
C27—C28 | 1.395 (11) | C95—H95 | 0.9300 |
C28—C29 | 1.378 (12) | C96—C97 | 1.423 (14) |
C28—H28 | 0.9300 | C96—C104 | 1.441 (12) |
C29—C30 | 1.365 (12) | C97—C98 | 1.287 (14) |
C29—H29 | 0.9300 | C97—H97 | 0.9300 |
C30—C31 | 1.385 (12) | C98—C99 | 1.462 (15) |
C30—H30 | 0.9300 | C98—H98 | 0.9300 |
C31—C32 | 1.382 (11) | C99—C100 | 1.357 (14) |
C31—H31 | 0.9300 | C99—C103 | 1.418 (12) |
C32—H32 | 0.9300 | C100—C101 | 1.338 (15) |
C33—C34 | 1.509 (10) | C100—H100 | 0.9300 |
C34—C35 | 1.332 (12) | C101—C102 | 1.412 (13) |
C34—C42 | 1.474 (12) | C101—H101 | 0.9300 |
C35—C36 | 1.470 (14) | C102—H102 | 0.9300 |
C35—H35 | 0.9300 | C103—C104 | 1.420 (13) |
C36—C41 | 1.357 (15) | C105—C106 | 1.388 (12) |
C36—C37 | 1.400 (16) | C105—H105 | 0.9300 |
C37—C38 | 1.444 (17) | C106—C107 | 1.344 (13) |
C37—H37 | 0.9300 | C106—H106 | 0.9300 |
C38—C39 | 1.349 (17) | C107—C108 | 1.397 (13) |
C38—H38 | 0.9300 | C107—H107 | 0.9300 |
C39—C40 | 1.376 (18) | C108—C116 | 1.428 (11) |
C39—H39 | 0.9300 | C108—C109 | 1.431 (13) |
C40—C41 | 1.415 (16) | C109—C110 | 1.300 (13) |
C40—H40 | 0.9300 | C109—H109 | 0.9300 |
C41—H41 | 0.9300 | C110—C111 | 1.453 (12) |
C42—C47 | 1.377 (13) | C110—H110 | 0.9300 |
C42—C43 | 1.408 (13) | C111—C112 | 1.385 (13) |
C43—C44 | 1.412 (14) | C111—C115 | 1.398 (12) |
C43—H43 | 0.9300 | C112—C113 | 1.357 (13) |
C44—C45 | 1.301 (15) | C112—H112 | 0.9300 |
C44—H44 | 0.9300 | C113—C114 | 1.393 (12) |
C45—C46 | 1.362 (15) | C113—H113 | 0.9300 |
C45—H45 | 0.9300 | C114—H114 | 0.9300 |
C46—C47 | 1.421 (13) | C115—C116 | 1.433 (12) |
C46—H46 | 0.9300 | ||
O7—La1—O9 | 71.71 (17) | C44—C45—C46 | 125.7 (12) |
O7—La1—O3 | 83.80 (18) | C44—C45—H45 | 117.1 |
O9—La1—O3 | 133.01 (17) | C46—C45—H45 | 117.1 |
O7—La1—O2 | 95.19 (18) | C45—C46—C47 | 115.4 (11) |
O9—La1—O2 | 80.78 (17) | C45—C46—H46 | 122.3 |
O3—La1—O2 | 142.35 (17) | C47—C46—H46 | 122.3 |
O7—La1—O5 | 111.75 (18) | C42—C47—C46 | 121.9 (10) |
O9—La1—O5 | 79.10 (17) | C42—C47—H47 | 119.1 |
O3—La1—O5 | 73.63 (17) | C46—C47—H47 | 119.1 |
O2—La1—O5 | 138.85 (18) | O10—C48—O9 | 124.9 (7) |
O7—La1—O13 | 78.69 (19) | O10—C48—C49 | 117.0 (7) |
O9—La1—O13 | 135.67 (18) | O9—C48—C49 | 118.1 (7) |
O3—La1—O13 | 73.25 (17) | C50—C49—C57 | 126.0 (7) |
O2—La1—O13 | 69.69 (18) | C50—C49—C48 | 118.0 (7) |
O5—La1—O13 | 143.78 (19) | C57—C49—C48 | 115.5 (7) |
O7—La1—N1 | 149.7 (2) | C49—C50—C51 | 132.1 (8) |
O9—La1—N1 | 138.6 (2) | C49—C50—H50 | 114.0 |
O3—La1—N1 | 74.5 (2) | C51—C50—H50 | 114.0 |
O2—La1—N1 | 89.6 (2) | C56—C51—C52 | 117.6 (8) |
O5—La1—N1 | 82.48 (19) | C56—C51—C50 | 125.9 (8) |
O13—La1—N1 | 74.9 (2) | C52—C51—C50 | 116.4 (8) |
O7—La1—N2 | 149.2 (2) | C53—C52—C51 | 121.2 (9) |
O9—La1—N2 | 78.96 (19) | C53—C52—H52 | 119.4 |
O3—La1—N2 | 124.42 (19) | C51—C52—H52 | 119.4 |
O2—La1—N2 | 70.48 (18) | C54—C53—C52 | 120.6 (10) |
O5—La1—N2 | 70.65 (19) | C54—C53—H53 | 119.7 |
O13—La1—N2 | 118.50 (19) | C52—C53—H53 | 119.7 |
N1—La1—N2 | 59.9 (2) | C53—C54—C55 | 119.2 (9) |
O11—La2—O4 | 88.9 (2) | C53—C54—H54 | 120.4 |
O11—La2—O6 | 81.5 (2) | C55—C54—H54 | 120.4 |
O4—La2—O6 | 73.2 (2) | C54—C55—C56 | 120.2 (10) |
O11—La2—O10 | 137.06 (18) | C54—C55—H55 | 119.9 |
O4—La2—O10 | 117.42 (18) | C56—C55—H55 | 119.9 |
O6—La2—O10 | 75.47 (19) | C51—C56—C55 | 121.2 (9) |
O11—La2—O8 | 140.35 (18) | C51—C56—H56 | 119.4 |
O4—La2—O8 | 89.07 (18) | C55—C56—H56 | 119.4 |
O6—La2—O8 | 135.09 (18) | C58—C57—C62 | 117.2 (9) |
O10—La2—O8 | 77.16 (17) | C58—C57—C49 | 122.2 (8) |
O11—La2—O14 | 71.45 (17) | C62—C57—C49 | 120.5 (8) |
O4—La2—O14 | 73.82 (19) | C57—C58—C59 | 120.5 (9) |
O6—La2—O14 | 137.28 (19) | C57—C58—H58 | 119.8 |
O10—La2—O14 | 145.25 (17) | C59—C58—H58 | 119.8 |
O8—La2—O14 | 70.00 (16) | C60—C59—C58 | 119.3 (10) |
O11—La2—N4 | 88.6 (2) | C60—C59—H59 | 120.4 |
O4—La2—N4 | 150.0 (2) | C58—C59—H59 | 120.4 |
O6—La2—N4 | 135.7 (2) | C61—C60—C59 | 122.3 (11) |
O10—La2—N4 | 83.50 (19) | C61—C60—H60 | 118.8 |
O8—La2—N4 | 74.23 (19) | C59—C60—H60 | 118.8 |
O14—La2—N4 | 77.1 (2) | C60—C61—C62 | 119.6 (11) |
O11—La2—N3 | 70.1 (2) | C60—C61—H61 | 120.2 |
O4—La2—N3 | 146.0 (2) | C62—C61—H61 | 120.2 |
O6—La2—N3 | 77.3 (2) | C57—C62—C61 | 121.1 (10) |
O10—La2—N3 | 69.76 (18) | C57—C62—H62 | 119.5 |
O8—La2—N3 | 124.3 (2) | C61—C62—H62 | 119.5 |
O14—La2—N3 | 120.75 (19) | O8—C63—O7 | 122.2 (6) |
N4—La2—N3 | 58.8 (2) | O8—C63—C64 | 118.4 (6) |
C1—O2—La1 | 141.2 (5) | O7—C63—C64 | 119.4 (7) |
C18—O3—La1 | 121.4 (5) | C65—C64—C72 | 123.5 (6) |
C18—O4—La2 | 151.4 (5) | C65—C64—C63 | 117.1 (6) |
C33—O5—La1 | 135.3 (5) | C72—C64—C63 | 119.5 (6) |
C33—O6—La2 | 148.9 (6) | C64—C65—C66 | 126.7 (7) |
C63—O7—La1 | 175.0 (5) | C64—C65—H65 | 116.6 |
C63—O8—La2 | 112.3 (4) | C66—C65—H65 | 116.6 |
C48—O9—La1 | 131.6 (5) | C71—C66—C67 | 118.7 (8) |
C48—O10—La2 | 139.2 (5) | C71—C66—C65 | 121.8 (8) |
C78—O11—La2 | 144.4 (5) | C67—C66—C65 | 119.4 (8) |
C16—O13—La1 | 137.0 (5) | C66—C67—C68 | 121.1 (10) |
C105—N1—C116 | 118.1 (8) | C66—C67—H67 | 119.4 |
C105—N1—La1 | 120.1 (6) | C68—C67—H67 | 119.5 |
C116—N1—La1 | 121.8 (6) | C69—C68—C67 | 120.1 (10) |
C114—N2—C115 | 116.7 (7) | C69—C68—H68 | 119.9 |
C114—N2—La1 | 121.5 (5) | C67—C68—H68 | 119.9 |
C115—N2—La1 | 121.8 (6) | C68—C69—C70 | 119.5 (10) |
C102—N3—C103 | 117.6 (8) | C68—C69—H69 | 120.2 |
C102—N3—La2 | 120.4 (6) | C70—C69—H69 | 120.2 |
C103—N3—La2 | 122.0 (6) | C69—C70—C71 | 119.7 (11) |
C93—N4—C104 | 118.6 (8) | C69—C70—H70 | 120.1 |
C93—N4—La2 | 118.7 (6) | C71—C70—H70 | 120.1 |
C104—N4—La2 | 122.7 (6) | C66—C71—C70 | 120.7 (10) |
O1—C1—O2 | 125.2 (8) | C66—C71—H71 | 119.7 |
O1—C1—C2 | 116.6 (6) | C70—C71—H71 | 119.7 |
O2—C1—C2 | 118.1 (7) | C73—C72—C77 | 118.3 (7) |
C3—C2—C10 | 123.8 (8) | C73—C72—C64 | 118.8 (7) |
C3—C2—C1 | 119.2 (7) | C77—C72—C64 | 122.9 (7) |
C10—C2—C1 | 116.7 (7) | C72—C73—C74 | 121.0 (8) |
C2—C3—C4 | 129.2 (8) | C72—C73—H73 | 119.5 |
C2—C3—H3 | 115.4 | C74—C73—H73 | 119.5 |
C4—C3—H3 | 115.4 | C75—C74—C73 | 119.3 (9) |
C9—C4—C5 | 118.4 (9) | C75—C74—H74 | 120.3 |
C9—C4—C3 | 124.4 (9) | C73—C74—H74 | 120.3 |
C5—C4—C3 | 117.2 (9) | C74—C75—C76 | 121.4 (9) |
C6—C5—C4 | 119.9 (10) | C74—C75—H75 | 119.3 |
C6—C5—H5 | 120.1 | C76—C75—H75 | 119.3 |
C4—C5—H5 | 120.1 | C75—C76—C77 | 119.1 (9) |
C7—C6—C5 | 119.7 (11) | C75—C76—H76 | 120.4 |
C7—C6—H6 | 120.1 | C77—C76—H76 | 120.4 |
C5—C6—H6 | 120.1 | C72—C77—C76 | 120.8 (8) |
C6—C7—C8 | 124.0 (12) | C72—C77—H77 | 119.6 |
C6—C7—H7 | 118.0 | C76—C77—H77 | 119.6 |
C8—C7—H7 | 118.0 | O12—C78—O11 | 123.9 (7) |
C7—C8—C9 | 118.3 (11) | O12—C78—C79 | 118.9 (7) |
C7—C8—H8 | 120.9 | O11—C78—C79 | 117.2 (7) |
C9—C8—H8 | 120.9 | C86—C79—C80 | 125.4 (7) |
C4—C9—C8 | 119.7 (10) | C86—C79—C78 | 118.8 (7) |
C4—C9—H9 | 120.2 | C80—C79—C78 | 115.8 (7) |
C8—C9—H9 | 120.2 | C81—C80—C85 | 117.2 (8) |
C11—C10—C15 | 118.0 (7) | C81—C80—C79 | 123.3 (7) |
C11—C10—C2 | 121.8 (7) | C85—C80—C79 | 119.4 (8) |
C15—C10—C2 | 120.1 (8) | C82—C81—C80 | 120.9 (8) |
C10—C11—C12 | 122.0 (8) | C82—C81—H81 | 119.5 |
C10—C11—H11 | 119.0 | C80—C81—H81 | 119.5 |
C12—C11—H11 | 119.0 | C83—C82—C81 | 120.9 (9) |
C13—C12—C11 | 120.1 (9) | C83—C82—H82 | 119.5 |
C13—C12—H12 | 119.9 | C81—C82—H82 | 119.5 |
C11—C12—H12 | 119.9 | C82—C83—C84 | 120.4 (9) |
C12—C13—C14 | 119.3 (8) | C82—C83—H83 | 119.8 |
C12—C13—H13 | 120.3 | C84—C83—H83 | 119.8 |
C14—C13—H13 | 120.3 | C83—C84—C85 | 118.8 (9) |
C13—C14—C15 | 120.9 (9) | C83—C84—H84 | 120.6 |
C13—C14—H14 | 119.6 | C85—C84—H84 | 120.6 |
C15—C14—H14 | 119.6 | C84—C85—C80 | 121.6 (9) |
C10—C15—C14 | 119.7 (9) | C84—C85—H85 | 119.2 |
C10—C15—H15 | 120.2 | C80—C85—H85 | 119.2 |
C14—C15—H15 | 120.2 | C79—C86—C87 | 131.1 (8) |
O13—C16—C17 | 113.6 (10) | C79—C86—H86 | 114.5 |
O13—C16—H16A | 108.8 | C87—C86—H86 | 114.5 |
C17—C16—H16A | 108.8 | C92—C87—C88 | 116.9 (8) |
O13—C16—H16B | 108.8 | C92—C87—C86 | 118.5 (8) |
C17—C16—H16B | 108.8 | C88—C87—C86 | 124.1 (8) |
H16A—C16—H16B | 107.7 | C87—C88—C89 | 121.4 (9) |
C16—C17—H17A | 109.5 | C87—C88—H88 | 119.3 |
C16—C17—H17B | 109.5 | C89—C88—H88 | 119.3 |
H17A—C17—H17B | 109.5 | C90—C89—C88 | 119.6 (10) |
C16—C17—H17C | 109.5 | C90—C89—H89 | 120.2 |
H17A—C17—H17C | 109.5 | C88—C89—H89 | 120.2 |
H17B—C17—H17C | 109.5 | C91—C90—C89 | 121.0 (10) |
O4—C18—O3 | 123.2 (7) | C91—C90—H90 | 119.5 |
O4—C18—C19 | 119.3 (7) | C89—C90—H90 | 119.5 |
O3—C18—C19 | 117.5 (7) | C90—C91—C92 | 118.9 (10) |
C20—C19—C27 | 124.3 (7) | C90—C91—H91 | 120.5 |
C20—C19—C18 | 118.6 (7) | C92—C91—H91 | 120.5 |
C27—C19—C18 | 117.0 (6) | C87—C92—C91 | 122.0 (10) |
C19—C20—C21 | 131.1 (8) | C87—C92—H92 | 119.0 |
C19—C20—H20 | 114.5 | C91—C92—H92 | 119.0 |
C21—C20—H20 | 114.5 | N4—C93—C94 | 122.1 (9) |
C22—C21—C26 | 117.9 (8) | N4—C93—H93 | 118.9 |
C22—C21—C20 | 118.9 (8) | C94—C93—H93 | 118.9 |
C26—C21—C20 | 123.1 (8) | C95—C94—C93 | 118.2 (10) |
C21—C22—C23 | 121.4 (10) | C95—C94—H94 | 120.9 |
C21—C22—H22 | 119.3 | C93—C94—H94 | 120.9 |
C23—C22—H22 | 119.3 | C94—C95—C96 | 123.0 (10) |
C24—C23—C22 | 120.2 (10) | C94—C95—H95 | 118.5 |
C24—C23—H23 | 119.9 | C96—C95—H95 | 118.5 |
C22—C23—H23 | 119.9 | C95—C96—C97 | 125.2 (10) |
C23—C24—C25 | 119.7 (10) | C95—C96—C104 | 117.0 (9) |
C23—C24—H24 | 120.1 | C97—C96—C104 | 117.8 (10) |
C25—C24—H24 | 120.1 | C98—C97—C96 | 121.6 (11) |
C24—C25—C26 | 121.3 (10) | C98—C97—H97 | 119.2 |
C24—C25—H25 | 119.4 | C96—C97—H97 | 119.2 |
C26—C25—H25 | 119.4 | C97—C98—C99 | 124.4 (10) |
C25—C26—C21 | 119.4 (9) | C97—C98—H98 | 117.8 |
C25—C26—H26 | 120.3 | C99—C98—H98 | 117.8 |
C21—C26—H26 | 120.3 | C100—C99—C103 | 117.8 (11) |
C32—C27—C28 | 117.2 (8) | C100—C99—C98 | 126.4 (10) |
C32—C27—C19 | 121.0 (7) | C103—C99—C98 | 115.7 (10) |
C28—C27—C19 | 121.7 (7) | C101—C100—C99 | 121.6 (10) |
C29—C28—C27 | 121.2 (9) | C101—C100—H100 | 119.2 |
C29—C28—H28 | 119.4 | C99—C100—H100 | 119.2 |
C27—C28—H28 | 119.4 | C100—C101—C102 | 118.8 (11) |
C30—C29—C28 | 120.6 (9) | C100—C101—H101 | 120.6 |
C30—C29—H29 | 119.7 | C102—C101—H101 | 120.6 |
C28—C29—H29 | 119.7 | N3—C102—C101 | 122.2 (10) |
C29—C30—C31 | 119.7 (9) | N3—C102—H102 | 118.9 |
C29—C30—H30 | 120.2 | C101—C102—H102 | 118.9 |
C31—C30—H30 | 120.2 | N3—C103—C104 | 117.5 (8) |
C30—C31—C32 | 119.6 (9) | N3—C103—C99 | 122.0 (9) |
C30—C31—H31 | 120.2 | C104—C103—C99 | 120.5 (10) |
C32—C31—H31 | 120.2 | N4—C104—C103 | 118.9 (8) |
C31—C32—C27 | 121.7 (8) | N4—C104—C96 | 121.1 (9) |
C31—C32—H32 | 119.2 | C103—C104—C96 | 120.0 (9) |
C27—C32—H32 | 119.2 | N1—C105—C106 | 124.2 (10) |
O5—C33—O6 | 124.4 (7) | N1—C105—H105 | 117.9 |
O5—C33—C34 | 118.3 (8) | C106—C105—H105 | 117.9 |
O6—C33—C34 | 117.3 (8) | C107—C106—C105 | 118.7 (10) |
C35—C34—C42 | 123.3 (8) | C107—C106—H106 | 120.6 |
C35—C34—C33 | 118.2 (8) | C105—C106—H106 | 120.6 |
C42—C34—C33 | 118.5 (8) | C106—C107—C108 | 120.4 (9) |
C34—C35—C36 | 128.5 (10) | C106—C107—H107 | 119.8 |
C34—C35—H35 | 115.7 | C108—C107—H107 | 119.8 |
C36—C35—H35 | 115.7 | C107—C108—C116 | 117.5 (9) |
C41—C36—C37 | 120.0 (12) | C107—C108—C109 | 125.8 (9) |
C41—C36—C35 | 121.9 (12) | C116—C108—C109 | 116.6 (9) |
C37—C36—C35 | 118.0 (11) | C110—C109—C108 | 124.4 (9) |
C36—C37—C38 | 116.9 (13) | C110—C109—H109 | 117.8 |
C36—C37—H37 | 121.5 | C108—C109—H109 | 117.8 |
C38—C37—H37 | 121.5 | C109—C110—C111 | 120.1 (9) |
C39—C38—C37 | 120.9 (15) | C109—C110—H110 | 120.0 |
C39—C38—H38 | 119.6 | C111—C110—H110 | 120.0 |
C37—C38—H38 | 119.6 | C112—C111—C115 | 117.0 (9) |
C38—C39—C40 | 122.2 (15) | C112—C111—C110 | 123.6 (9) |
C38—C39—H39 | 118.9 | C115—C111—C110 | 119.4 (9) |
C40—C39—H39 | 118.9 | C113—C112—C111 | 121.3 (9) |
C39—C40—C41 | 116.5 (13) | C113—C112—H112 | 119.3 |
C39—C40—H40 | 121.7 | C111—C112—H112 | 119.3 |
C41—C40—H40 | 121.7 | C112—C113—C114 | 118.1 (10) |
C36—C41—C40 | 123.0 (13) | C112—C113—H113 | 120.9 |
C36—C41—H41 | 118.5 | C114—C113—H113 | 120.9 |
C40—C41—H41 | 118.5 | N2—C114—C113 | 123.7 (9) |
C47—C42—C43 | 118.5 (9) | N2—C114—H114 | 118.1 |
C47—C42—C34 | 121.1 (9) | C113—C114—H114 | 118.1 |
C43—C42—C34 | 120.4 (9) | N2—C115—C111 | 123.1 (9) |
C42—C43—C44 | 118.6 (11) | N2—C115—C116 | 117.6 (7) |
C42—C43—H43 | 120.7 | C111—C115—C116 | 119.3 (8) |
C44—C43—H43 | 120.7 | N1—C116—C108 | 121.0 (9) |
C45—C44—C43 | 119.7 (12) | N1—C116—C115 | 118.8 (7) |
C45—C44—H44 | 120.1 | C108—C116—C115 | 120.2 (8) |
C43—C44—H44 | 120.1 | ||
O7—La1—O2—C1 | 87.6 (8) | La2—O6—C33—O5 | −34.7 (17) |
O9—La1—O2—C1 | 158.1 (8) | La2—O6—C33—C34 | 145.6 (8) |
O3—La1—O2—C1 | 1.1 (9) | O5—C33—C34—C35 | 160.5 (9) |
O5—La1—O2—C1 | −140.4 (8) | O6—C33—C34—C35 | −19.8 (13) |
O13—La1—O2—C1 | 11.7 (8) | O5—C33—C34—C42 | −16.6 (13) |
N1—La1—O2—C1 | −62.4 (8) | O6—C33—C34—C42 | 163.1 (9) |
N2—La1—O2—C1 | −120.4 (8) | C42—C34—C35—C36 | −8.1 (18) |
O7—La1—O3—C18 | 63.0 (6) | C33—C34—C35—C36 | 174.9 (11) |
O9—La1—O3—C18 | 5.3 (6) | C34—C35—C36—C41 | −45 (2) |
O2—La1—O3—C18 | 153.5 (5) | C34—C35—C36—C37 | 133.7 (14) |
O5—La1—O3—C18 | −51.8 (5) | C41—C36—C37—C38 | 1 (2) |
O13—La1—O3—C18 | 143.1 (6) | C35—C36—C37—C38 | −178.2 (12) |
N1—La1—O3—C18 | −138.4 (6) | C36—C37—C38—C39 | −4 (2) |
N2—La1—O3—C18 | −103.5 (6) | C37—C38—C39—C40 | 8 (3) |
O11—La2—O4—C18 | 103.5 (11) | C38—C39—C40—C41 | −8 (2) |
O6—La2—O4—C18 | 22.1 (10) | C37—C36—C41—C40 | −1 (2) |
O10—La2—O4—C18 | −41.1 (11) | C35—C36—C41—C40 | 177.5 (12) |
O8—La2—O4—C18 | −116.1 (11) | C39—C40—C41—C36 | 5 (2) |
O14—La2—O4—C18 | 174.5 (11) | C35—C34—C42—C47 | 133.2 (11) |
N4—La2—O4—C18 | −171.2 (9) | C33—C34—C42—C47 | −49.8 (13) |
N3—La2—O4—C18 | 53.1 (12) | C35—C34—C42—C43 | −47.8 (14) |
O7—La1—O5—C33 | 6.2 (9) | C33—C34—C42—C43 | 129.1 (9) |
O9—La1—O5—C33 | −58.9 (8) | C47—C42—C43—C44 | −3.4 (14) |
O3—La1—O5—C33 | 82.4 (8) | C34—C42—C43—C44 | 177.7 (9) |
O2—La1—O5—C33 | −120.9 (8) | C42—C43—C44—C45 | 3.3 (16) |
O13—La1—O5—C33 | 107.0 (8) | C43—C44—C45—C46 | −2.9 (18) |
N1—La1—O5—C33 | 158.4 (8) | C44—C45—C46—C47 | 2.4 (17) |
N2—La1—O5—C33 | −140.9 (8) | C43—C42—C47—C46 | 3.0 (14) |
O11—La2—O6—C33 | −119.9 (11) | C34—C42—C47—C46 | −178.0 (9) |
O4—La2—O6—C33 | −28.5 (11) | C45—C46—C47—C42 | −2.4 (15) |
O10—La2—O6—C33 | 96.6 (11) | La2—O10—C48—O9 | 42.3 (12) |
O8—La2—O6—C33 | 42.4 (12) | La2—O10—C48—C49 | −137.4 (6) |
O14—La2—O6—C33 | −69.4 (12) | La1—O9—C48—O10 | −61.2 (9) |
N4—La2—O6—C33 | 160.9 (10) | La1—O9—C48—C49 | 118.6 (7) |
N3—La2—O6—C33 | 168.7 (11) | O10—C48—C49—C50 | 165.2 (7) |
O9—La1—O7—C63 | −54 (6) | O9—C48—C49—C50 | −14.5 (11) |
O3—La1—O7—C63 | 166 (6) | O10—C48—C49—C57 | −7.4 (10) |
O2—La1—O7—C63 | 24 (6) | O9—C48—C49—C57 | 172.9 (7) |
O5—La1—O7—C63 | −124 (6) | C57—C49—C50—C51 | −2.1 (15) |
O13—La1—O7—C63 | 92 (6) | C48—C49—C50—C51 | −173.8 (8) |
N1—La1—O7—C63 | 122 (6) | C49—C50—C51—C56 | −15.1 (16) |
N2—La1—O7—C63 | −36 (6) | C49—C50—C51—C52 | 166.2 (9) |
O11—La2—O8—C63 | 148.2 (5) | C56—C51—C52—C53 | 1.0 (15) |
O4—La2—O8—C63 | 61.0 (5) | C50—C51—C52—C53 | 179.8 (9) |
O6—La2—O8—C63 | −3.8 (7) | C51—C52—C53—C54 | −0.8 (16) |
O10—La2—O8—C63 | −57.4 (5) | C52—C53—C54—C55 | 0.3 (16) |
O14—La2—O8—C63 | 134.1 (6) | C53—C54—C55—C56 | 0.0 (16) |
N4—La2—O8—C63 | −144.2 (6) | C52—C51—C56—C55 | −0.6 (15) |
N3—La2—O8—C63 | −111.6 (5) | C50—C51—C56—C55 | −179.4 (9) |
O7—La1—O9—C48 | −12.5 (6) | C54—C55—C56—C51 | 0.1 (16) |
O3—La1—O9—C48 | 49.9 (7) | C50—C49—C57—C58 | 106.7 (11) |
O2—La1—O9—C48 | −111.1 (6) | C48—C49—C57—C58 | −81.3 (11) |
O5—La1—O9—C48 | 105.0 (6) | C50—C49—C57—C62 | −75.3 (12) |
O13—La1—O9—C48 | −63.1 (7) | C48—C49—C57—C62 | 96.6 (10) |
N1—La1—O9—C48 | 170.2 (5) | C62—C57—C58—C59 | −1.5 (14) |
N2—La1—O9—C48 | 177.2 (6) | C49—C57—C58—C59 | 176.4 (9) |
O11—La2—O10—C48 | −133.9 (7) | C57—C58—C59—C60 | −0.1 (16) |
O4—La2—O10—C48 | −12.1 (8) | C58—C59—C60—C61 | 1.0 (18) |
O6—La2—O10—C48 | −74.0 (7) | C59—C60—C61—C62 | −0.2 (18) |
O8—La2—O10—C48 | 70.0 (7) | C58—C57—C62—C61 | 2.3 (14) |
O14—La2—O10—C48 | 89.2 (8) | C49—C57—C62—C61 | −175.7 (9) |
N4—La2—O10—C48 | 145.2 (7) | C60—C61—C62—C57 | −1.5 (16) |
N3—La2—O10—C48 | −155.6 (8) | La2—O8—C63—O7 | −13.1 (10) |
O4—La2—O11—C78 | 74.9 (10) | La2—O8—C63—C64 | 165.3 (5) |
O6—La2—O11—C78 | 148.1 (10) | La1—O7—C63—O8 | 136 (5) |
O10—La2—O11—C78 | −154.1 (9) | La1—O7—C63—C64 | −43 (6) |
O8—La2—O11—C78 | −12.4 (12) | O8—C63—C64—C65 | −159.3 (8) |
O14—La2—O11—C78 | 1.6 (10) | O7—C63—C64—C65 | 19.2 (12) |
N4—La2—O11—C78 | −75.2 (10) | O8—C63—C64—C72 | 21.1 (11) |
N3—La2—O11—C78 | −132.4 (10) | O7—C63—C64—C72 | −160.4 (7) |
O7—La1—O13—C16 | 51.0 (9) | C72—C64—C65—C66 | −9.1 (14) |
O9—La1—O13—C16 | 99.5 (9) | C63—C64—C65—C66 | 171.4 (8) |
O3—La1—O13—C16 | −35.8 (9) | C64—C65—C66—C71 | −52.0 (14) |
O2—La1—O13—C16 | 150.9 (10) | C64—C65—C66—C67 | 132.4 (10) |
O5—La1—O13—C16 | −60.5 (10) | C71—C66—C67—C68 | 3.6 (15) |
N1—La1—O13—C16 | −113.8 (9) | C65—C66—C67—C68 | 179.3 (9) |
N2—La1—O13—C16 | −156.4 (9) | C66—C67—C68—C69 | −4.6 (16) |
O7—La1—N1—C105 | 12.5 (8) | C67—C68—C69—C70 | 2.1 (17) |
O9—La1—N1—C105 | −172.5 (5) | C68—C69—C70—C71 | 1.2 (17) |
O3—La1—N1—C105 | −33.4 (6) | C67—C66—C71—C70 | −0.1 (15) |
O2—La1—N1—C105 | 112.1 (6) | C65—C66—C71—C70 | −175.7 (9) |
O5—La1—N1—C105 | −108.4 (6) | C69—C70—C71—C66 | −2.3 (16) |
O13—La1—N1—C105 | 43.0 (6) | C65—C64—C72—C73 | −54.7 (12) |
N2—La1—N1—C105 | 179.6 (7) | C63—C64—C72—C73 | 124.9 (8) |
O7—La1—N1—C116 | −169.6 (5) | C65—C64—C72—C77 | 127.0 (9) |
O9—La1—N1—C116 | 5.4 (7) | C63—C64—C72—C77 | −53.5 (11) |
O3—La1—N1—C116 | 144.5 (6) | C77—C72—C73—C74 | −0.3 (12) |
O2—La1—N1—C116 | −70.1 (6) | C64—C72—C73—C74 | −178.7 (8) |
O5—La1—N1—C116 | 69.5 (6) | C72—C73—C74—C75 | −0.2 (13) |
O13—La1—N1—C116 | −139.1 (6) | C73—C74—C75—C76 | 0.4 (14) |
N2—La1—N1—C116 | −2.5 (5) | C74—C75—C76—C77 | −0.1 (14) |
O7—La1—N2—C114 | −11.4 (8) | C73—C72—C77—C76 | 0.7 (12) |
O9—La1—N2—C114 | 6.6 (6) | C64—C72—C77—C76 | 179.0 (8) |
O3—La1—N2—C114 | 141.7 (6) | C75—C76—C77—C72 | −0.5 (13) |
O2—La1—N2—C114 | −77.4 (6) | La2—O11—C78—O12 | −12.9 (17) |
O5—La1—N2—C114 | 88.8 (6) | La2—O11—C78—C79 | 167.3 (6) |
O13—La1—N2—C114 | −129.7 (6) | O12—C78—C79—C86 | 175.4 (9) |
N1—La1—N2—C114 | −178.7 (7) | O11—C78—C79—C86 | −4.9 (13) |
O7—La1—N2—C115 | 169.7 (5) | O12—C78—C79—C80 | −3.8 (13) |
O9—La1—N2—C115 | −172.2 (6) | O11—C78—C79—C80 | 175.9 (8) |
O3—La1—N2—C115 | −37.1 (6) | C86—C79—C80—C81 | −113.3 (10) |
O2—La1—N2—C115 | 103.8 (6) | C78—C79—C80—C81 | 65.9 (11) |
O5—La1—N2—C115 | −90.0 (6) | C86—C79—C80—C85 | 67.4 (12) |
O13—La1—N2—C115 | 51.4 (6) | C78—C79—C80—C85 | −113.5 (9) |
N1—La1—N2—C115 | 2.5 (5) | C85—C80—C81—C82 | −2.3 (12) |
O11—La2—N3—C102 | −77.0 (6) | C79—C80—C81—C82 | 178.3 (7) |
O4—La2—N3—C102 | −21.9 (8) | C80—C81—C82—C83 | 1.6 (13) |
O6—La2—N3—C102 | 8.5 (6) | C81—C82—C83—C84 | 0.9 (14) |
O10—La2—N3—C102 | 87.4 (6) | C82—C83—C84—C85 | −2.6 (14) |
O8—La2—N3—C102 | 144.9 (6) | C83—C84—C85—C80 | 1.8 (13) |
O14—La2—N3—C102 | −129.5 (6) | C81—C80—C85—C84 | 0.6 (12) |
N4—La2—N3—C102 | −177.8 (7) | C79—C80—C85—C84 | 180.0 (7) |
O11—La2—N3—C103 | 102.0 (6) | C80—C79—C86—C87 | 8.1 (16) |
O4—La2—N3—C103 | 157.1 (6) | C78—C79—C86—C87 | −171.0 (9) |
O6—La2—N3—C103 | −172.6 (6) | C79—C86—C87—C92 | −165.9 (11) |
O10—La2—N3—C103 | −93.6 (6) | C79—C86—C87—C88 | 22.0 (18) |
O8—La2—N3—C103 | −36.1 (7) | C92—C87—C88—C89 | 0.7 (17) |
O14—La2—N3—C103 | 49.5 (7) | C86—C87—C88—C89 | 172.8 (10) |
N4—La2—N3—C103 | 1.1 (6) | C87—C88—C89—C90 | 1.8 (18) |
O11—La2—N4—C93 | 112.2 (6) | C88—C89—C90—C91 | −2 (2) |
O4—La2—N4—C93 | 26.8 (8) | C89—C90—C91—C92 | 1 (2) |
O6—La2—N4—C93 | −171.5 (6) | C88—C87—C92—C91 | −2.5 (19) |
O10—La2—N4—C93 | −110.1 (6) | C86—C87—C92—C91 | −175.1 (11) |
O8—La2—N4—C93 | −31.7 (6) | C90—C91—C92—C87 | 2 (2) |
O14—La2—N4—C93 | 40.9 (6) | C104—N4—C93—C94 | 0.7 (13) |
N3—La2—N4—C93 | 179.6 (7) | La2—N4—C93—C94 | 178.8 (7) |
O11—La2—N4—C104 | −69.7 (6) | N4—C93—C94—C95 | −0.7 (14) |
O4—La2—N4—C104 | −155.1 (6) | C93—C94—C95—C96 | 0.5 (15) |
O6—La2—N4—C104 | 6.6 (7) | C94—C95—C96—C97 | 177.8 (9) |
O10—La2—N4—C104 | 68.0 (6) | C94—C95—C96—C104 | −0.3 (15) |
O8—La2—N4—C104 | 146.4 (6) | C95—C96—C97—C98 | −177.2 (10) |
O14—La2—N4—C104 | −141.0 (6) | C104—C96—C97—C98 | 0.9 (14) |
N3—La2—N4—C104 | −2.3 (6) | C96—C97—C98—C99 | −1.9 (16) |
La1—O2—C1—O1 | −20.2 (14) | C97—C98—C99—C100 | 178.9 (10) |
La1—O2—C1—C2 | 157.0 (6) | C97—C98—C99—C103 | 1.8 (15) |
O1—C1—C2—C3 | 163.3 (8) | C103—C99—C100—C101 | −1.8 (15) |
O2—C1—C2—C3 | −14.2 (11) | C98—C99—C100—C101 | −178.8 (10) |
O1—C1—C2—C10 | −10.7 (11) | C99—C100—C101—C102 | 0.7 (15) |
O2—C1—C2—C10 | 171.8 (7) | C103—N3—C102—C101 | 0.0 (13) |
C10—C2—C3—C4 | −1.3 (14) | La2—N3—C102—C101 | 179.0 (6) |
C1—C2—C3—C4 | −174.8 (8) | C100—C101—C102—N3 | 0.2 (14) |
C2—C3—C4—C9 | −35.5 (15) | C102—N3—C103—C104 | 179.0 (8) |
C2—C3—C4—C5 | 146.3 (9) | La2—N3—C103—C104 | 0.0 (10) |
C9—C4—C5—C6 | 2.3 (14) | C102—N3—C103—C99 | −1.2 (12) |
C3—C4—C5—C6 | −179.4 (9) | La2—N3—C103—C99 | 179.8 (6) |
C4—C5—C6—C7 | −3.2 (15) | C100—C99—C103—N3 | 2.1 (14) |
C5—C6—C7—C8 | 3.4 (17) | C98—C99—C103—N3 | 179.4 (8) |
C6—C7—C8—C9 | −2.6 (17) | C100—C99—C103—C104 | −178.1 (9) |
C5—C4—C9—C8 | −1.5 (14) | C98—C99—C103—C104 | −0.8 (13) |
C3—C4—C9—C8 | −179.7 (9) | C93—N4—C104—C103 | −178.6 (8) |
C7—C8—C9—C4 | 1.6 (15) | La2—N4—C104—C103 | 3.4 (10) |
C3—C2—C10—C11 | −75.4 (12) | C93—N4—C104—C96 | −0.5 (12) |
C1—C2—C10—C11 | 98.3 (10) | La2—N4—C104—C96 | −178.6 (6) |
C3—C2—C10—C15 | 101.9 (11) | N3—C103—C104—N4 | −2.1 (12) |
C1—C2—C10—C15 | −84.4 (11) | C99—C103—C104—N4 | 178.0 (8) |
C15—C10—C11—C12 | 1.1 (15) | N3—C103—C104—C96 | 179.7 (8) |
C2—C10—C11—C12 | 178.4 (9) | C99—C103—C104—C96 | −0.1 (13) |
C10—C11—C12—C13 | −2.1 (16) | C95—C96—C104—N4 | 0.3 (13) |
C11—C12—C13—C14 | 2.2 (16) | C97—C96—C104—N4 | −177.9 (8) |
C12—C13—C14—C15 | −1.3 (16) | C95—C96—C104—C103 | 178.4 (8) |
C11—C10—C15—C14 | −0.2 (14) | C97—C96—C104—C103 | 0.1 (13) |
C2—C10—C15—C14 | −177.6 (9) | C116—N1—C105—C106 | 1.3 (13) |
C13—C14—C15—C10 | 0.3 (16) | La1—N1—C105—C106 | 179.2 (6) |
La1—O13—C16—C17 | 149.5 (8) | N1—C105—C106—C107 | 0.0 (14) |
La2—O4—C18—O3 | 73.6 (13) | C105—C106—C107—C108 | −2.1 (13) |
La2—O4—C18—C19 | −104.6 (11) | C106—C107—C108—C116 | 2.9 (13) |
La1—O3—C18—O4 | −45.0 (10) | C106—C107—C108—C109 | −177.5 (9) |
La1—O3—C18—C19 | 133.2 (6) | C107—C108—C109—C110 | −178.9 (9) |
O4—C18—C19—C20 | −6.6 (12) | C116—C108—C109—C110 | 0.7 (14) |
O3—C18—C19—C20 | 175.1 (7) | C108—C109—C110—C111 | 1.2 (15) |
O4—C18—C19—C27 | 172.9 (7) | C109—C110—C111—C112 | 177.6 (10) |
O3—C18—C19—C27 | −5.5 (11) | C109—C110—C111—C115 | −1.7 (14) |
C27—C19—C20—C21 | −1.7 (15) | C115—C111—C112—C113 | −1.0 (14) |
C18—C19—C20—C21 | 177.7 (8) | C110—C111—C112—C113 | 179.7 (9) |
C19—C20—C21—C22 | 159.8 (9) | C111—C112—C113—C114 | 0.5 (14) |
C19—C20—C21—C26 | −24.1 (15) | C115—N2—C114—C113 | 1.5 (12) |
C26—C21—C22—C23 | 1.6 (15) | La1—N2—C114—C113 | −177.3 (7) |
C20—C21—C22—C23 | 178.0 (9) | C112—C113—C114—N2 | −0.7 (14) |
C21—C22—C23—C24 | 0.0 (17) | C114—N2—C115—C111 | −2.2 (12) |
C22—C23—C24—C25 | −1.7 (17) | La1—N2—C115—C111 | 176.7 (6) |
C23—C24—C25—C26 | 1.7 (17) | C114—N2—C115—C116 | 178.8 (7) |
C24—C25—C26—C21 | 0.0 (16) | La1—N2—C115—C116 | −2.4 (9) |
C22—C21—C26—C25 | −1.6 (15) | C112—C111—C115—N2 | 1.9 (13) |
C20—C21—C26—C25 | −177.8 (9) | C110—C111—C115—N2 | −178.7 (8) |
C20—C19—C27—C32 | 105.4 (10) | C112—C111—C115—C116 | −179.0 (8) |
C18—C19—C27—C32 | −74.0 (9) | C110—C111—C115—C116 | 0.3 (12) |
C20—C19—C27—C28 | −72.2 (11) | C105—N1—C116—C108 | −0.4 (12) |
C18—C19—C27—C28 | 108.4 (9) | La1—N1—C116—C108 | −178.3 (6) |
C32—C27—C28—C29 | −1.9 (12) | C105—N1—C116—C115 | −179.6 (7) |
C19—C27—C28—C29 | 175.8 (8) | La1—N1—C116—C115 | 2.5 (10) |
C27—C28—C29—C30 | 0.4 (14) | C107—C108—C116—N1 | −1.7 (12) |
C28—C29—C30—C31 | 0.9 (14) | C109—C108—C116—N1 | 178.7 (7) |
C29—C30—C31—C32 | −0.7 (14) | C107—C108—C116—C115 | 177.5 (8) |
C30—C31—C32—C27 | −0.9 (13) | C109—C108—C116—C115 | −2.1 (12) |
C28—C27—C32—C31 | 2.2 (12) | N2—C115—C116—N1 | −0.1 (11) |
C19—C27—C32—C31 | −175.6 (7) | C111—C115—C116—N1 | −179.2 (7) |
La1—O5—C33—O6 | 3.6 (14) | N2—C115—C116—C108 | −179.3 (7) |
La1—O5—C33—C34 | −176.7 (6) | C111—C115—C116—C108 | 1.6 (12) |
Experimental details
Crystal data | |
Chemical formula | [La2(C15H11O2)6(C12H8N2)2(C2H6O)(H2O)] |
Mr | 2041.74 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 13.464 (3), 18.572 (4), 20.490 (4) |
α, β, γ (°) | 77.42 (3), 89.01 (3), 77.94 (3) |
V (Å3) | 4887.9 (17) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.93 |
Crystal size (mm) | 0.38 × 0.27 × 0.10 |
Data collection | |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.719, 0.913 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 38229, 17208, 11202 |
Rint | 0.056 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.059, 0.169, 1.16 |
No. of reflections | 17208 |
No. of parameters | 1226 |
No. of restraints | 960 |
H-atom treatment | H-atom parameters constrained |
w = 1/[σ2(Fo2) + (0.0596P)2 + 10.5654P] where P = (Fo2 + 2Fc2)/3 | |
Δρmax, Δρmin (e Å−3) | 1.36, −1.22 |
Computer programs: PROCESS-AUTO (Rigaku, 1998), CrystalStructure (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Photochromism, a photoinduced reversible transformation between two chemical forms having different absorption spectra, i.e. different colours, is both of great basic interest and of high application potential (Dürr & Bouas-Laurent, 2003). Among all the photochromic families, diarylethenes are some of the most efficient compounds used for photoswitching applications because of their thermal irreversibility, high fatigue resistance, and good photoconversion yield between an open form and a closed form (Irie, 2002). For these reasons, numerous recent advances focused on diarylethene photochemistry have been reported (Tsuboi et al., 2009). Organic–inorganic hybrids based on diarylethene moieties have attracted particular interest for their varied structures, novel photophysical and/or photochemical phenomena and fascinating properties (Wenger et al., 2004; Busby et al., 2005; Yam et al., 2004; Ko et al., 2006).
In our recent work, we have become interested in preparing self-assembled organic–inorganic hybrid materials by dint of either coordinate bonds or coulomb interactions based on organic templates (Chai et al., 2007a,b, 2009, 2010). With the aim of constructing organic–inorganic hybrids in the field of coordinate chemistry, the carboxylate ligands are versatile candidates which can adopt several chelating bidentate and/or different carboxylate-bridging coordinate modes. Additionally, a carboxylate group in a bridging mode provides an efficient pathway that couples magnetic or luminescent metal centres for ferromagnetic interaction or energy transfer (Oldham et al., 1987; Faulkner & Pope, 2003). Phenylcinnamic acid (PCA) is a monocarboxylic acid in which two arene rings are connected by π-conjugated ethylene, and the diarylethene unit could show typical photochromic transformation (see second scheme) (Dürr & Bouas-Laurent, 2003). Previously, Kumagai and co-workers synthesized and characterized some transition metal complexes using PCA- as a ligand, but neither photochromic nor luminescent properties were reported (Kumagai et al., 2003, 2005; Oka & Inoue, 2004). In this study, we have focused on the construction of novel organic–inorganic complexes by utilizing PCA- as a ligand and rare earth ions as metal centres, and the title novel photochromic dinuclear compound, (I), has been successfully synthesized. Considering the photochromism derived from the PCA- ligand and the photoluminescence displayed by rare earth ions, this novel hybrid may be endowed with new functions, such as luminescence modulation by photochromic switching.
The structure of (I) has been characterized as a dinuclear cluster (Fig. 1), consisting of two LaIII cations, six PCA- anions, two 1,10-phenanthroline (phen) ligands, one ethanol molecule and one water molecule. Each crystallographically independent LaIII cation adopts a distorted [LaO6N2] bicapped trigonal–prismatic coordination geometry, with one capping site occupied up by a coordinating solvent (ethanol or water) and the other occupied by half a phen ligand (Fig. 2). The La—O [2.398 (5)–2.620 (5) Å] and La—N [2.722 (7)–2.772 (7) Å] bond lengths are similar to previously reported values (Khanjani et al., 2010). The two La centres are connected by four bridging PCA- ligands to form the dinuclear cluster. Each La coordination polyhedron is completed by one monodentate PCA- ligand, one bidentate phen ligand and one coordinated solvent molecule (ethanol or water). Previous reports (Kumagai et al., 2003, 2005; Oka & Inoue, 2004) have described two coordination modes for the PCA- ligand, bridged and tricoordinated. In the dinuclear metal–carboxylate cluster of (I), the tricoordinated mode means that one of the O atoms is coordinated to a single metal centre while the other is within coordinating distance of both metal centres. The terminal PCA- ligands observed in (I) thus appear to be unprecedented in this type of complex. The configurations of the PCA- ligands in the complex are almost the same. All six atoms in and around the C═C bonds are essentially coplanar, while the two phenyl rings are in a syn–syn mode with a dihedral angle of about 70°.
Previously, some dinuclear La cluster compounds have been synthesized from carboxylate and neutral ligands. Focusing on the structural features of the cluster core, there are two modes that have been observed to construct such clusters. In the first mode, also seen in a dinuclear Nd cluster we reported recently (Chai et al., 2009), two carboxylate groups bridge the La centres to form a dinuclear La2 cluster (Li et al., 2007; Gao, 2009) and the remaining coordination sites are occupied by other anionic and neutral ligands. In the second mode, four carboxylate groups bridge the La centres to form a dinuclear unit, with two groups adopting a µ2-bridged arrangement and the other two adopting a tricoordinated mode (Lu et al., 1996; Shi et al., 2001; Zheng & Jin, 2003; Lu et al., 2001; Fu et al., 2004; Zhu et al., 2005; Liu et al., 2008). Here, the structure of the cluster core is notably different from the reported examples. The difference may be due to the large size of the PCA- ligand and the steric crowding it creates around the cluster core. Seen along the La1···La2 axis, this La2(PCA)4 unit looks like a windmill (Fig. 3). The two remaining PCA- ligands adopt a mono-coordinated mode, with a phen ligand and a coordinating solvent molecule completing the remaining coordination sites on each side of the windmill-like unit. O—H···O hydrogen bonding links the noncoordinated carboxylate O atom of the monodentate PCA- ligand to the solvent molecule coordinated to each La centre [O13···O1 = 2.600 (8) Å and O14···O12 = 2.653 (8) Å].
As the PCA- ligand contains a feature of a potentially photochromic molecule (Dürr & Bouas-Laurent, 2003), the photochromism of (I) has been observed roughly. When a colourless ethanolic solution of (I) is irradiated with UV light for some minutes, a gradual colour change to yellow occurs (see second scheme). Similar behaviour is shown by a powder sample of (I), though the transformation is slower than that in solution. The corresponding Eu3+ and Tb3+ samples have also been synthesized due to their expected luminescent properties. Detailed analyses of their spectroscopic properties are ongoing.