


Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810038109/bh2313sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536810038109/bh2313Isup2.hkl |
CCDC reference: 797685
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean
(C-C) = 0.006 Å
- Disorder in main residue
- R factor = 0.034
- wR factor = 0.101
- Data-to-parameter ratio = 17.9
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O6 PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for O8 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for La PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for O2 PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N3
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.42 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.58 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for O8 -- N4 .. 5.61 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O9 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O11 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O12 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C28 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N5 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C24 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C27 PLAT334_ALERT_2_C Small Average Benzene C-C Dist. C24 -C29 1.37 Ang. PLAT412_ALERT_2_C Short Intra XH3 .. XHn H19A .. H23A .. 1.83 Ang. PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 66.00 A 3 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 1 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 10 PLAT480_ALERT_4_C Long H...A H-Bond Reported H2A .. O6 .. 2.65 Ang. PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 103
Alert level G PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) La -- O6 .. 14.47 su PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) La -- O8 .. 10.97 su PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) La -- O9 .. 9.48 su PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) La -- O11 .. 6.17 su PLAT232_ALERT_2_G Hirshfeld Test Diff (M-X) La -- O12 .. 6.47 su PLAT301_ALERT_3_G Note: Main Residue Disorder ................... 2.00 Perc. PLAT380_ALERT_4_G Check Incorrectly? Oriented X(sp2)-Methyl Moiety C15 PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ...... 32.10 Deg. O5' -N3 -O5 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 5 ALERT level B = Potentially serious problem 19 ALERT level C = Check and explain 8 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 25 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Reagents and solvents are commercially available and were not purified before use. The Schiff base ligand 2-[(4-methylphenyl)iminomethyl]-6-methoxy-phenol was synthesized by condensation of o-vanillin and p-methylaniline. The title complex was obtained by adding La(NO3)3 (1 mmol, dissolved in 20 ml methanol) to N-salicylidene-p-toluidine (2 mmol) in methanol. The mixture was stirred for 8 h at room temperature. The resulting solid was then filtered out and the reddish-brown solution was kept aside. Red crystals were obtained after several days.
The structure was solved by direct methods and successive Fourier difference synthesis. The H atoms bonded to C and N atoms were positioned geometrically and refined using a riding model [aliphatic C—H =0.96 Å (Uiso(H) = 1.5Ueq(C)), aromatic C—H = 0.93 Å (Uiso(H) = 1.2Ueq(C)) and N—H = 0.86 Å, Uiso(H) = 1.2Ueq(N)]. H atom of the hydroxyl group in methanol, H14, was found in a difference map and refined freely.
Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); 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).
![]() | Fig. 1. The molecular structure of the title complex, showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. |
[La(NO3)3(C15H15NO2)2(CH4O)] | Z = 2 |
Mr = 839.54 | F(000) = 848 |
Triclinic, P1 | Dx = 1.546 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.8616 (2) Å | Cell parameters from 9937 reflections |
b = 14.6502 (5) Å | θ = 1.5–27.7° |
c = 16.6470 (5) Å | µ = 1.26 mm−1 |
α = 73.210 (2)° | T = 296 K |
β = 85.648 (2)° | Block, red |
γ = 79.320 (1)° | 0.43 × 0.31 × 0.20 mm |
V = 1803.26 (9) Å3 |
Bruker APEXII CCD area-detector diffractometer | 8464 independent reflections |
Radiation source: fine-focus sealed tube | 7465 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
ϕ and ω scans | θmax = 27.7°, θmin = 1.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→10 |
Tmin = 0.634, Tmax = 0.783 | k = −19→18 |
30011 measured reflections | l = −21→21 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | w = 1/[σ2(Fo2) + (0.0579P)2 + 0.8812P] where P = (Fo2 + 2Fc2)/3 |
8464 reflections | (Δ/σ)max = 0.001 |
473 parameters | Δρmax = 1.23 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
0 constraints |
[La(NO3)3(C15H15NO2)2(CH4O)] | γ = 79.320 (1)° |
Mr = 839.54 | V = 1803.26 (9) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.8616 (2) Å | Mo Kα radiation |
b = 14.6502 (5) Å | µ = 1.26 mm−1 |
c = 16.6470 (5) Å | T = 296 K |
α = 73.210 (2)° | 0.43 × 0.31 × 0.20 mm |
β = 85.648 (2)° |
Bruker APEXII CCD area-detector diffractometer | 8464 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 7465 reflections with I > 2σ(I) |
Tmin = 0.634, Tmax = 0.783 | Rint = 0.024 |
30011 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 1.23 e Å−3 |
8464 reflections | Δρmin = −0.51 e Å−3 |
473 parameters |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
La | 0.50959 (2) | 0.172767 (11) | 0.194416 (10) | 0.04293 (7) | |
O1 | 0.3524 (3) | 0.32578 (16) | 0.11163 (14) | 0.0509 (5) | |
O2 | 0.4089 (4) | 0.20682 (18) | 0.01876 (17) | 0.0673 (7) | |
O3 | 0.4311 (3) | 0.05673 (16) | 0.32705 (14) | 0.0534 (5) | |
O4 | 0.2435 (3) | 0.23100 (17) | 0.30077 (18) | 0.0668 (7) | |
O5 | 0.665 (2) | 0.0504 (12) | 0.1156 (11) | 0.093 (5) | 0.50 |
O5' | 0.610 (3) | 0.0211 (12) | 0.1433 (13) | 0.118 (7) | 0.50 |
O6 | 0.7262 (5) | −0.0014 (2) | 0.2482 (2) | 0.0983 (11) | |
O7 | 0.8172 (5) | −0.0934 (3) | 0.1712 (3) | 0.1174 (14) | |
O8 | 0.8476 (4) | 0.1764 (3) | 0.17935 (19) | 0.0857 (9) | |
O9 | 0.7128 (4) | 0.2593 (2) | 0.06973 (19) | 0.0807 (9) | |
O10 | 0.9881 (4) | 0.2497 (3) | 0.0703 (2) | 0.0941 (11) | |
O11 | 0.5728 (4) | 0.32810 (17) | 0.22884 (17) | 0.0652 (6) | |
O12 | 0.6419 (4) | 0.19922 (19) | 0.32788 (15) | 0.0659 (6) | |
O13 | 0.6879 (4) | 0.3357 (2) | 0.34005 (19) | 0.0815 (8) | |
O14 | 0.2457 (4) | 0.1086 (3) | 0.1706 (2) | 0.0912 (11) | |
N1 | 0.2882 (4) | 0.50830 (19) | 0.11960 (17) | 0.0521 (6) | |
H1A | 0.3398 | 0.4502 | 0.1421 | 0.063* | |
N2 | 0.5013 (3) | −0.12440 (19) | 0.41794 (17) | 0.0486 (6) | |
H2A | 0.5240 | −0.0801 | 0.3738 | 0.058* | |
N3 | 0.7281 (5) | −0.0207 (2) | 0.1827 (3) | 0.0753 (9) | |
N4 | 0.8512 (4) | 0.2286 (2) | 0.10540 (19) | 0.0582 (7) | |
N5 | 0.6358 (4) | 0.2885 (2) | 0.29964 (18) | 0.0542 (6) | |
C1 | 0.2592 (5) | 0.4606 (2) | −0.0041 (2) | 0.0548 (8) | |
C2 | 0.3205 (4) | 0.3609 (2) | 0.03234 (19) | 0.0453 (6) | |
C3 | 0.3459 (4) | 0.3002 (2) | −0.0216 (2) | 0.0523 (7) | |
C4 | 0.3071 (6) | 0.3360 (3) | −0.1045 (2) | 0.0694 (10) | |
H4A | 0.3238 | 0.2945 | −0.1386 | 0.083* | |
C5 | 0.2422 (7) | 0.4346 (3) | −0.1392 (2) | 0.0822 (13) | |
H5A | 0.2164 | 0.4580 | −0.1959 | 0.099* | |
C6 | 0.2170 (7) | 0.4957 (3) | −0.0904 (2) | 0.0775 (12) | |
H6A | 0.1720 | 0.5608 | −0.1133 | 0.093* | |
C7 | 0.2388 (5) | 0.5277 (2) | 0.0433 (2) | 0.0611 (9) | |
H7A | 0.1858 | 0.5907 | 0.0177 | 0.073* | |
C8 | 0.4344 (12) | 0.1407 (4) | −0.0311 (5) | 0.162 (4) | |
H8C | 0.4955 | 0.0794 | 0.0006 | 0.194* | |
H8A | 0.5006 | 0.1657 | −0.0808 | 0.194* | |
H8B | 0.3240 | 0.1327 | −0.0465 | 0.194* | |
C9 | 0.2656 (4) | 0.5737 (2) | 0.1702 (2) | 0.0512 (7) | |
C10 | 0.3521 (6) | 0.5460 (3) | 0.2447 (3) | 0.0675 (10) | |
H10A | 0.4255 | 0.4866 | 0.2605 | 0.081* | |
C11 | 0.3294 (6) | 0.6071 (3) | 0.2957 (3) | 0.0724 (11) | |
H11A | 0.3875 | 0.5882 | 0.3460 | 0.087* | |
C12 | 0.2219 (5) | 0.6955 (3) | 0.2731 (3) | 0.0651 (9) | |
C13 | 0.1410 (6) | 0.7226 (3) | 0.1976 (3) | 0.0747 (11) | |
H13A | 0.0713 | 0.7832 | 0.1808 | 0.090* | |
C14 | 0.1595 (6) | 0.6631 (3) | 0.1459 (3) | 0.0683 (10) | |
H14A | 0.1018 | 0.6826 | 0.0954 | 0.082* | |
C15 | 0.1923 (7) | 0.7602 (4) | 0.3311 (4) | 0.0954 (16) | |
H15A | 0.1148 | 0.8187 | 0.3055 | 0.143* | |
H15B | 0.3008 | 0.7758 | 0.3409 | 0.143* | |
H15C | 0.1427 | 0.7272 | 0.3834 | 0.143* | |
C16 | 0.3056 (4) | −0.0007 (2) | 0.4620 (2) | 0.0464 (7) | |
C17 | 0.3251 (4) | 0.0727 (2) | 0.3862 (2) | 0.0463 (6) | |
C18 | 0.2207 (4) | 0.1652 (2) | 0.3780 (2) | 0.0535 (7) | |
C19 | 0.1127 (5) | 0.1833 (3) | 0.4407 (3) | 0.0617 (9) | |
H19A | 0.0462 | 0.2444 | 0.4338 | 0.074* | |
C20 | 0.0999 (5) | 0.1110 (3) | 0.5159 (3) | 0.0654 (10) | |
H20A | 0.0266 | 0.1249 | 0.5589 | 0.078* | |
C21 | 0.1928 (5) | 0.0211 (3) | 0.5269 (2) | 0.0574 (8) | |
H21A | 0.1826 | −0.0264 | 0.5771 | 0.069* | |
C22 | 0.3935 (4) | −0.0961 (2) | 0.4727 (2) | 0.0495 (7) | |
H22A | 0.3732 | −0.1422 | 0.5225 | 0.059* | |
C23 | 0.1142 (7) | 0.3155 (3) | 0.2773 (4) | 0.108 (2) | |
H23A | 0.0386 | 0.3197 | 0.3247 | 0.162* | |
H23B | 0.0483 | 0.3120 | 0.2324 | 0.162* | |
H23C | 0.1687 | 0.3718 | 0.2591 | 0.162* | |
C24 | 0.5857 (4) | −0.2201 (2) | 0.4228 (2) | 0.0514 (7) | |
C25 | 0.6855 (6) | −0.2367 (3) | 0.3564 (3) | 0.0787 (12) | |
H25A | 0.6994 | −0.1853 | 0.3096 | 0.094* | |
C26 | 0.7662 (6) | −0.3292 (3) | 0.3578 (3) | 0.0841 (13) | |
H26A | 0.8345 | −0.3387 | 0.3118 | 0.101* | |
C27 | 0.7489 (6) | −0.4063 (3) | 0.4239 (3) | 0.0730 (11) | |
C28 | 0.6463 (9) | −0.3883 (3) | 0.4903 (3) | 0.1021 (18) | |
H28A | 0.6307 | −0.4400 | 0.5365 | 0.122* | |
C29 | 0.5661 (8) | −0.2968 (3) | 0.4906 (3) | 0.0885 (15) | |
H29A | 0.4988 | −0.2871 | 0.5368 | 0.106* | |
C30 | 0.8370 (9) | −0.5076 (4) | 0.4238 (4) | 0.109 (2) | |
H30A | 0.8078 | −0.5530 | 0.4750 | 0.163* | |
H30B | 0.9602 | −0.5103 | 0.4195 | 0.163* | |
H30C | 0.7988 | −0.5234 | 0.3769 | 0.163* | |
C31 | 0.1924 (9) | 0.0164 (4) | 0.2049 (5) | 0.137 (3) | |
H31A | 0.0837 | 0.0174 | 0.1818 | 0.205* | |
H31B | 0.1798 | 0.0030 | 0.2648 | 0.205* | |
H31C | 0.2781 | −0.0330 | 0.1912 | 0.205* | |
H14 | 0.166 (8) | 0.151 (4) | 0.140 (4) | 0.107 (18)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
La | 0.04001 (10) | 0.03162 (10) | 0.05135 (11) | −0.00059 (6) | −0.00069 (7) | −0.00613 (7) |
O1 | 0.0568 (13) | 0.0394 (11) | 0.0507 (12) | 0.0028 (9) | −0.0089 (10) | −0.0083 (9) |
O2 | 0.0818 (18) | 0.0450 (13) | 0.0776 (17) | 0.0009 (12) | −0.0210 (14) | −0.0238 (12) |
O3 | 0.0528 (12) | 0.0415 (11) | 0.0574 (13) | −0.0024 (9) | 0.0127 (10) | −0.0076 (10) |
O4 | 0.0578 (14) | 0.0412 (12) | 0.0850 (17) | 0.0052 (10) | 0.0178 (13) | −0.0056 (12) |
O5 | 0.110 (12) | 0.067 (7) | 0.104 (8) | 0.032 (6) | −0.050 (7) | −0.043 (6) |
O5' | 0.101 (11) | 0.094 (12) | 0.174 (18) | 0.049 (8) | −0.058 (10) | −0.087 (12) |
O6 | 0.119 (3) | 0.071 (2) | 0.086 (2) | 0.0160 (19) | 0.017 (2) | −0.0171 (17) |
O7 | 0.124 (3) | 0.079 (2) | 0.137 (3) | 0.052 (2) | −0.015 (3) | −0.052 (2) |
O8 | 0.0601 (16) | 0.105 (2) | 0.0719 (18) | −0.0099 (16) | −0.0042 (14) | 0.0051 (17) |
O9 | 0.0552 (16) | 0.095 (2) | 0.0764 (18) | −0.0136 (15) | −0.0031 (13) | 0.0012 (16) |
O10 | 0.0467 (14) | 0.114 (3) | 0.093 (2) | −0.0199 (16) | 0.0056 (14) | 0.0177 (19) |
O11 | 0.0798 (17) | 0.0453 (13) | 0.0675 (15) | −0.0025 (12) | −0.0209 (13) | −0.0115 (11) |
O12 | 0.0837 (18) | 0.0540 (15) | 0.0525 (13) | −0.0075 (13) | −0.0064 (12) | −0.0044 (11) |
O13 | 0.083 (2) | 0.096 (2) | 0.0820 (19) | −0.0218 (17) | −0.0105 (15) | −0.0456 (17) |
O14 | 0.0644 (18) | 0.075 (2) | 0.118 (3) | −0.0223 (16) | −0.0334 (18) | 0.0124 (19) |
N1 | 0.0589 (16) | 0.0360 (13) | 0.0546 (15) | 0.0036 (11) | 0.0003 (12) | −0.0096 (11) |
N2 | 0.0531 (15) | 0.0417 (14) | 0.0496 (14) | −0.0111 (11) | −0.0007 (11) | −0.0091 (11) |
N3 | 0.067 (2) | 0.0517 (18) | 0.103 (3) | 0.0121 (16) | −0.003 (2) | −0.0288 (19) |
N4 | 0.0460 (15) | 0.0540 (17) | 0.0614 (17) | −0.0079 (12) | −0.0002 (13) | 0.0039 (13) |
N5 | 0.0507 (15) | 0.0585 (17) | 0.0544 (15) | −0.0073 (13) | 0.0012 (12) | −0.0192 (13) |
C1 | 0.065 (2) | 0.0433 (17) | 0.0476 (16) | −0.0017 (15) | 0.0010 (15) | −0.0053 (13) |
C2 | 0.0413 (15) | 0.0434 (16) | 0.0487 (16) | −0.0046 (12) | −0.0021 (12) | −0.0103 (13) |
C3 | 0.0495 (17) | 0.0488 (18) | 0.0593 (18) | −0.0070 (14) | −0.0040 (14) | −0.0166 (15) |
C4 | 0.084 (3) | 0.069 (3) | 0.060 (2) | −0.011 (2) | −0.0033 (19) | −0.0273 (19) |
C5 | 0.121 (4) | 0.071 (3) | 0.0464 (19) | −0.008 (3) | −0.010 (2) | −0.0080 (18) |
C6 | 0.114 (4) | 0.051 (2) | 0.055 (2) | 0.000 (2) | −0.009 (2) | −0.0021 (17) |
C7 | 0.079 (2) | 0.0389 (17) | 0.0545 (19) | 0.0021 (16) | 0.0017 (17) | −0.0045 (14) |
C8 | 0.268 (10) | 0.070 (3) | 0.159 (6) | 0.047 (5) | −0.110 (7) | −0.072 (4) |
C9 | 0.0521 (17) | 0.0398 (16) | 0.0586 (18) | −0.0004 (13) | 0.0020 (14) | −0.0145 (14) |
C10 | 0.080 (3) | 0.0431 (18) | 0.073 (2) | 0.0112 (17) | −0.016 (2) | −0.0168 (17) |
C11 | 0.086 (3) | 0.057 (2) | 0.075 (2) | 0.002 (2) | −0.020 (2) | −0.0235 (19) |
C12 | 0.061 (2) | 0.054 (2) | 0.086 (3) | −0.0032 (17) | −0.0025 (19) | −0.0319 (19) |
C13 | 0.078 (3) | 0.051 (2) | 0.091 (3) | 0.0182 (19) | −0.013 (2) | −0.029 (2) |
C14 | 0.075 (2) | 0.051 (2) | 0.071 (2) | 0.0181 (18) | −0.0130 (19) | −0.0204 (17) |
C15 | 0.103 (4) | 0.078 (3) | 0.121 (4) | 0.002 (3) | −0.016 (3) | −0.060 (3) |
C16 | 0.0428 (15) | 0.0488 (17) | 0.0517 (16) | −0.0143 (13) | −0.0006 (12) | −0.0164 (13) |
C17 | 0.0391 (14) | 0.0462 (16) | 0.0559 (17) | −0.0101 (12) | 0.0028 (12) | −0.0170 (14) |
C18 | 0.0452 (16) | 0.0453 (17) | 0.069 (2) | −0.0086 (13) | 0.0073 (14) | −0.0165 (15) |
C19 | 0.0544 (19) | 0.056 (2) | 0.079 (2) | −0.0056 (16) | 0.0100 (17) | −0.0302 (18) |
C20 | 0.059 (2) | 0.081 (3) | 0.067 (2) | −0.0169 (19) | 0.0161 (17) | −0.040 (2) |
C21 | 0.059 (2) | 0.068 (2) | 0.0501 (17) | −0.0175 (17) | 0.0057 (15) | −0.0211 (16) |
C22 | 0.0530 (17) | 0.0502 (18) | 0.0459 (15) | −0.0155 (14) | −0.0042 (13) | −0.0098 (13) |
C23 | 0.085 (3) | 0.068 (3) | 0.124 (4) | 0.026 (2) | 0.030 (3) | 0.013 (3) |
C24 | 0.0543 (18) | 0.0441 (17) | 0.0582 (18) | −0.0107 (14) | −0.0079 (14) | −0.0149 (14) |
C25 | 0.091 (3) | 0.050 (2) | 0.088 (3) | −0.011 (2) | 0.025 (2) | −0.016 (2) |
C26 | 0.087 (3) | 0.065 (3) | 0.104 (3) | −0.010 (2) | 0.022 (3) | −0.037 (3) |
C27 | 0.080 (3) | 0.048 (2) | 0.096 (3) | −0.0049 (19) | −0.019 (2) | −0.026 (2) |
C28 | 0.160 (6) | 0.052 (2) | 0.082 (3) | −0.003 (3) | −0.004 (3) | −0.009 (2) |
C29 | 0.136 (4) | 0.053 (2) | 0.061 (2) | 0.000 (2) | 0.014 (3) | −0.0070 (19) |
C30 | 0.128 (5) | 0.064 (3) | 0.145 (5) | 0.008 (3) | −0.027 (4) | −0.054 (3) |
C31 | 0.117 (5) | 0.084 (4) | 0.205 (8) | −0.049 (4) | −0.060 (5) | 0.001 (4) |
La—O1 | 2.429 (2) | C8—H8A | 0.9600 |
La—O3 | 2.482 (2) | C8—H8B | 0.9600 |
La—O14 | 2.532 (3) | C9—C10 | 1.378 (5) |
La—O5' | 2.574 (19) | C9—C14 | 1.384 (5) |
La—O5 | 2.59 (2) | C10—C11 | 1.383 (5) |
La—O11 | 2.640 (2) | C10—H10A | 0.9300 |
La—O8 | 2.659 (3) | C11—C12 | 1.376 (5) |
La—O12 | 2.677 (3) | C11—H11A | 0.9300 |
La—O9 | 2.682 (3) | C12—C13 | 1.372 (6) |
La—O6 | 2.741 (3) | C12—C15 | 1.515 (5) |
La—O4 | 2.808 (2) | C13—C14 | 1.374 (5) |
La—O2 | 2.964 (3) | C13—H13A | 0.9300 |
O1—C2 | 1.296 (4) | C14—H14A | 0.9300 |
O2—C3 | 1.355 (4) | C15—H15A | 0.9600 |
O2—C8 | 1.426 (5) | C15—H15B | 0.9600 |
O3—C17 | 1.287 (4) | C15—H15C | 0.9600 |
O4—C18 | 1.388 (4) | C16—C22 | 1.406 (5) |
O4—C23 | 1.426 (5) | C16—C21 | 1.416 (5) |
O5—N3 | 1.342 (18) | C16—C17 | 1.422 (5) |
O5'—N3 | 1.15 (2) | C17—C18 | 1.423 (4) |
O6—N3 | 1.201 (5) | C18—C19 | 1.351 (5) |
O7—N3 | 1.218 (4) | C19—C20 | 1.397 (6) |
O8—N4 | 1.249 (4) | C19—H19A | 0.9300 |
O9—N4 | 1.225 (4) | C20—C21 | 1.350 (6) |
O10—N4 | 1.232 (4) | C20—H20A | 0.9300 |
O11—N5 | 1.248 (4) | C21—H21A | 0.9300 |
O12—N5 | 1.248 (4) | C22—H22A | 0.9300 |
O13—N5 | 1.230 (4) | C23—H23A | 0.9600 |
O14—C31 | 1.434 (6) | C23—H23B | 0.9600 |
O14—H14 | 0.87 (6) | C23—H23C | 0.9600 |
N1—C7 | 1.293 (4) | C24—C25 | 1.361 (5) |
N1—C9 | 1.428 (4) | C24—C29 | 1.366 (5) |
N1—H1A | 0.8600 | C25—C26 | 1.380 (6) |
N2—C22 | 1.301 (4) | C25—H25A | 0.9300 |
N2—C24 | 1.417 (4) | C26—C27 | 1.350 (7) |
N2—H2A | 0.8600 | C26—H26A | 0.9300 |
C1—C7 | 1.408 (5) | C27—C28 | 1.375 (7) |
C1—C2 | 1.416 (4) | C27—C30 | 1.518 (6) |
C1—C6 | 1.421 (5) | C28—C29 | 1.373 (6) |
C2—C3 | 1.416 (4) | C28—H28A | 0.9300 |
C3—C4 | 1.364 (5) | C29—H29A | 0.9300 |
C4—C5 | 1.403 (6) | C30—H30A | 0.9600 |
C4—H4A | 0.9300 | C30—H30B | 0.9600 |
C5—C6 | 1.354 (6) | C30—H30C | 0.9600 |
C5—H5A | 0.9300 | C31—H31A | 0.9600 |
C6—H6A | 0.9300 | C31—H31B | 0.9600 |
C7—H7A | 0.9300 | C31—H31C | 0.9600 |
C8—H8C | 0.9600 | ||
O1—La—O3 | 131.51 (8) | O1—C2—C3 | 120.9 (3) |
O1—La—O14 | 83.19 (10) | O1—C2—C1 | 121.9 (3) |
O3—La—O14 | 71.17 (10) | C3—C2—C1 | 117.2 (3) |
O1—La—O5' | 125.4 (5) | O2—C3—C4 | 126.2 (3) |
O3—La—O5' | 84.7 (4) | O2—C3—C2 | 112.6 (3) |
O14—La—O5' | 71.2 (4) | C4—C3—C2 | 121.2 (3) |
O1—La—O5 | 117.8 (4) | C3—C4—C5 | 120.8 (4) |
O3—La—O5 | 99.1 (3) | C3—C4—H4A | 119.6 |
O14—La—O5 | 82.3 (4) | C5—C4—H4A | 119.6 |
O5'—La—O5 | 15.8 (6) | C6—C5—C4 | 120.2 (4) |
O1—La—O11 | 64.68 (8) | C6—C5—H5A | 119.9 |
O3—La—O11 | 108.70 (8) | C4—C5—H5A | 119.9 |
O14—La—O11 | 136.91 (11) | C5—C6—C1 | 120.1 (4) |
O5'—La—O11 | 151.1 (4) | C5—C6—H6A | 119.9 |
O5—La—O11 | 137.2 (4) | C1—C6—H6A | 119.9 |
O1—La—O8 | 109.57 (9) | N1—C7—C1 | 125.0 (3) |
O3—La—O8 | 112.38 (8) | N1—C7—H7A | 117.5 |
O14—La—O8 | 151.69 (14) | C1—C7—H7A | 117.5 |
O5'—La—O8 | 81.0 (4) | O2—C8—H8C | 109.5 |
O5—La—O8 | 69.4 (4) | O2—C8—H8A | 109.5 |
O11—La—O8 | 70.22 (10) | H8C—C8—H8A | 109.5 |
O1—La—O12 | 109.48 (8) | O2—C8—H8B | 109.5 |
O3—La—O12 | 68.27 (8) | H8C—C8—H8B | 109.5 |
O14—La—O12 | 134.66 (11) | H8A—C8—H8B | 109.5 |
O5'—La—O12 | 123.0 (5) | C10—C9—C14 | 120.1 (3) |
O5—La—O12 | 123.1 (4) | C10—C9—N1 | 118.6 (3) |
O11—La—O12 | 47.22 (8) | C14—C9—N1 | 121.4 (3) |
O8—La—O12 | 66.28 (10) | C9—C10—C11 | 119.7 (3) |
O1—La—O9 | 69.51 (9) | C9—C10—H10A | 120.2 |
O3—La—O9 | 158.15 (9) | C11—C10—H10A | 120.2 |
O14—La—O9 | 123.52 (11) | C12—C11—C10 | 121.0 (4) |
O5'—La—O9 | 85.6 (4) | C12—C11—H11A | 119.5 |
O5—La—O9 | 69.8 (3) | C10—C11—H11A | 119.5 |
O11—La—O9 | 72.62 (10) | C13—C12—C11 | 118.3 (3) |
O8—La—O9 | 46.59 (9) | C13—C12—C15 | 121.2 (4) |
O12—La—O9 | 101.36 (9) | C11—C12—C15 | 120.5 (4) |
O1—La—O6 | 165.10 (9) | C12—C13—C14 | 122.1 (3) |
O3—La—O6 | 61.97 (9) | C12—C13—H13A | 118.9 |
O14—La—O6 | 97.88 (12) | C14—C13—H13A | 118.9 |
O5'—La—O6 | 42.8 (5) | C13—C14—C9 | 118.9 (4) |
O5—La—O6 | 48.1 (4) | C13—C14—H14A | 120.6 |
O11—La—O6 | 120.64 (11) | C9—C14—H14A | 120.6 |
O8—La—O6 | 63.33 (12) | C12—C15—H15A | 109.5 |
O12—La—O6 | 80.39 (10) | C12—C15—H15B | 109.5 |
O9—La—O6 | 98.05 (11) | H15A—C15—H15B | 109.5 |
O1—La—O4 | 74.24 (7) | C12—C15—H15C | 109.5 |
O3—La—O4 | 59.36 (7) | H15A—C15—H15C | 109.5 |
O14—La—O4 | 73.01 (12) | H15B—C15—H15C | 109.5 |
O5'—La—O4 | 135.7 (4) | C22—C16—C21 | 119.2 (3) |
O5—La—O4 | 151.3 (4) | C22—C16—C17 | 120.8 (3) |
O11—La—O4 | 71.17 (9) | C21—C16—C17 | 120.0 (3) |
O8—La—O4 | 134.08 (10) | O3—C17—C16 | 121.9 (3) |
O12—La—O4 | 69.48 (9) | O3—C17—C18 | 121.1 (3) |
O9—La—O4 | 136.83 (9) | C16—C17—C18 | 117.1 (3) |
O6—La—O4 | 120.37 (9) | C19—C18—O4 | 125.7 (3) |
O1—La—O2 | 56.74 (7) | C19—C18—C17 | 121.4 (3) |
O3—La—O2 | 131.40 (8) | O4—C18—C17 | 113.0 (3) |
O14—La—O2 | 62.19 (10) | C18—C19—C20 | 120.6 (3) |
O5'—La—O2 | 68.6 (5) | C18—C19—H19A | 119.7 |
O5—La—O2 | 63.1 (4) | C20—C19—H19A | 119.7 |
O11—La—O2 | 114.18 (7) | C21—C20—C19 | 120.9 (3) |
O8—La—O2 | 102.91 (9) | C21—C20—H20A | 119.6 |
O12—La—O2 | 160.04 (8) | C19—C20—H20A | 119.6 |
O9—La—O2 | 61.45 (9) | C20—C21—C16 | 120.1 (3) |
O6—La—O2 | 110.58 (9) | C20—C21—H21A | 120.0 |
O4—La—O2 | 115.03 (8) | C16—C21—H21A | 120.0 |
C2—O1—La | 133.08 (19) | N2—C22—C16 | 124.7 (3) |
C3—O2—C8 | 115.9 (4) | N2—C22—H22A | 117.7 |
C3—O2—La | 114.91 (19) | C16—C22—H22A | 117.7 |
C8—O2—La | 128.8 (3) | O4—C23—H23A | 109.5 |
C17—O3—La | 128.9 (2) | O4—C23—H23B | 109.5 |
C18—O4—C23 | 117.0 (3) | H23A—C23—H23B | 109.5 |
C18—O4—La | 117.00 (18) | O4—C23—H23C | 109.5 |
C23—O4—La | 125.3 (3) | H23A—C23—H23C | 109.5 |
N3—O5—La | 97.9 (10) | H23B—C23—H23C | 109.5 |
N3—O5'—La | 105.2 (13) | C25—C24—C29 | 118.7 (4) |
N3—O6—La | 94.6 (2) | C25—C24—N2 | 118.8 (3) |
N4—O8—La | 98.3 (2) | C29—C24—N2 | 122.5 (3) |
N4—O9—La | 97.8 (2) | C24—C25—C26 | 120.6 (4) |
N5—O11—La | 98.73 (19) | C24—C25—H25A | 119.7 |
N5—O12—La | 96.91 (18) | C26—C25—H25A | 119.7 |
C31—O14—La | 131.9 (3) | C27—C26—C25 | 121.9 (4) |
C31—O14—H14 | 112 (4) | C27—C26—H26A | 119.0 |
La—O14—H14 | 116 (4) | C25—C26—H26A | 119.0 |
C7—N1—C9 | 126.5 (3) | C26—C27—C28 | 116.8 (4) |
C7—N1—H1A | 116.7 | C26—C27—C30 | 121.1 (5) |
C9—N1—H1A | 116.7 | C28—C27—C30 | 122.1 (5) |
C22—N2—C24 | 127.3 (3) | C29—C28—C27 | 122.4 (5) |
C22—N2—H2A | 116.4 | C29—C28—H28A | 118.8 |
C24—N2—H2A | 116.4 | C27—C28—H28A | 118.8 |
O5'—N3—O6 | 112.0 (11) | C24—C29—C28 | 119.7 (4) |
O5'—N3—O7 | 123.3 (11) | C24—C29—H29A | 120.2 |
O6—N3—O7 | 122.0 (4) | C28—C29—H29A | 120.2 |
O5'—N3—O5 | 32.1 (13) | C27—C30—H30A | 109.5 |
O6—N3—O5 | 117.7 (9) | C27—C30—H30B | 109.5 |
O7—N3—O5 | 118.3 (9) | H30A—C30—H30B | 109.5 |
O9—N4—O10 | 121.4 (3) | C27—C30—H30C | 109.5 |
O9—N4—O8 | 117.3 (3) | H30A—C30—H30C | 109.5 |
O10—N4—O8 | 121.3 (3) | H30B—C30—H30C | 109.5 |
O13—N5—O11 | 121.3 (3) | O14—C31—H31A | 109.5 |
O13—N5—O12 | 121.6 (3) | O14—C31—H31B | 109.5 |
O11—N5—O12 | 117.1 (3) | H31A—C31—H31B | 109.5 |
C7—C1—C2 | 121.5 (3) | O14—C31—H31C | 109.5 |
C7—C1—C6 | 118.1 (3) | H31A—C31—H31C | 109.5 |
C2—C1—C6 | 120.4 (3) | H31B—C31—H31C | 109.5 |
O3—La—O1—C2 | −131.3 (3) | O1—La—O11—N5 | 161.2 (2) |
O14—La—O1—C2 | −74.0 (3) | O3—La—O11—N5 | 33.3 (2) |
O5'—La—O1—C2 | −12.8 (6) | O14—La—O11—N5 | 115.4 (2) |
O5—La—O1—C2 | 3.6 (5) | O5'—La—O11—N5 | −80.9 (10) |
O11—La—O1—C2 | 135.5 (3) | O5—La—O11—N5 | −94.4 (6) |
O8—La—O1—C2 | 80.0 (3) | O8—La—O11—N5 | −74.5 (2) |
O12—La—O1—C2 | 150.9 (3) | O12—La—O11—N5 | 1.05 (18) |
O9—La—O1—C2 | 55.7 (3) | O9—La—O11—N5 | −123.8 (2) |
O6—La—O1—C2 | 21.1 (5) | O6—La—O11—N5 | −34.6 (2) |
O4—La—O1—C2 | −148.2 (3) | O4—La—O11—N5 | 80.1 (2) |
O2—La—O1—C2 | −12.9 (3) | O2—La—O11—N5 | −170.17 (19) |
O1—La—O2—C3 | 9.7 (2) | O1—La—O12—N5 | −20.1 (2) |
O3—La—O2—C3 | 128.2 (2) | O3—La—O12—N5 | −148.1 (2) |
O14—La—O2—C3 | 110.3 (3) | O14—La—O12—N5 | −120.0 (2) |
O5'—La—O2—C3 | −170.3 (5) | O5'—La—O12—N5 | 144.1 (5) |
O5—La—O2—C3 | −154.0 (5) | O5—La—O12—N5 | 125.2 (4) |
O11—La—O2—C3 | −21.6 (3) | O11—La—O12—N5 | −1.04 (18) |
O8—La—O2—C3 | −95.5 (2) | O8—La—O12—N5 | 83.4 (2) |
O12—La—O2—C3 | −40.7 (4) | O9—La—O12—N5 | 52.0 (2) |
O9—La—O2—C3 | −73.5 (2) | O6—La—O12—N5 | 148.4 (2) |
O6—La—O2—C3 | −161.5 (2) | O4—La—O12—N5 | −84.0 (2) |
O4—La—O2—C3 | 58.0 (3) | O2—La—O12—N5 | 23.0 (4) |
O1—La—O2—C8 | −177.5 (6) | O1—La—O14—C31 | −171.4 (6) |
O3—La—O2—C8 | −58.9 (6) | O3—La—O14—C31 | −33.1 (6) |
O14—La—O2—C8 | −76.8 (6) | O5'—La—O14—C31 | 57.6 (8) |
O5'—La—O2—C8 | 2.6 (7) | O5—La—O14—C31 | 69.3 (7) |
O5—La—O2—C8 | 18.9 (7) | O11—La—O14—C31 | −130.7 (6) |
O11—La—O2—C8 | 151.3 (6) | O8—La—O14—C31 | 69.3 (7) |
O8—La—O2—C8 | 77.4 (6) | O12—La—O14—C31 | −60.6 (7) |
O12—La—O2—C8 | 132.1 (6) | O9—La—O14—C31 | 128.8 (6) |
O9—La—O2—C8 | 99.4 (6) | O6—La—O14—C31 | 23.6 (6) |
O6—La—O2—C8 | 11.3 (6) | O4—La—O14—C31 | −95.8 (6) |
O4—La—O2—C8 | −129.2 (6) | O2—La—O14—C31 | 132.8 (6) |
O1—La—O3—C17 | −25.9 (3) | La—O5'—N3—O6 | 24.1 (11) |
O14—La—O3—C17 | −87.9 (3) | La—O5'—N3—O7 | −174.5 (4) |
O5'—La—O3—C17 | −159.9 (5) | La—O5'—N3—O5 | −83 (3) |
O5—La—O3—C17 | −166.5 (5) | La—O6—N3—O5' | −21.8 (10) |
O11—La—O3—C17 | 46.5 (3) | La—O6—N3—O7 | 176.6 (4) |
O8—La—O3—C17 | 122.2 (3) | La—O6—N3—O5 | 13.1 (9) |
O12—La—O3—C17 | 71.4 (3) | La—O5—N3—O5' | 74 (3) |
O9—La—O3—C17 | 136.3 (3) | La—O5—N3—O6 | −13.9 (10) |
O6—La—O3—C17 | 161.9 (3) | La—O5—N3—O7 | −178.0 (4) |
O4—La—O3—C17 | −6.9 (2) | La—O9—N4—O10 | 179.3 (3) |
O2—La—O3—C17 | −104.6 (3) | La—O9—N4—O8 | −1.8 (4) |
O1—La—O4—C18 | 172.4 (3) | La—O8—N4—O9 | 1.9 (4) |
O3—La—O4—C18 | 7.0 (2) | La—O8—N4—O10 | −179.3 (3) |
O14—La—O4—C18 | 84.9 (2) | La—O11—N5—O13 | 178.8 (3) |
O5'—La—O4—C18 | 47.5 (7) | La—O11—N5—O12 | −1.8 (3) |
O5—La—O4—C18 | 52.8 (9) | La—O12—N5—O13 | −178.9 (3) |
O11—La—O4—C18 | −119.5 (2) | La—O12—N5—O11 | 1.8 (3) |
O8—La—O4—C18 | −85.4 (3) | La—O1—C2—C3 | 14.8 (4) |
O12—La—O4—C18 | −69.2 (2) | La—O1—C2—C1 | −165.3 (2) |
O9—La—O4—C18 | −153.9 (2) | C7—C1—C2—O1 | 3.6 (5) |
O6—La—O4—C18 | −4.4 (3) | C6—C1—C2—O1 | −176.7 (4) |
O2—La—O4—C18 | 131.9 (2) | C7—C1—C2—C3 | −176.5 (3) |
O1—La—O4—C23 | 2.6 (4) | C6—C1—C2—C3 | 3.2 (5) |
O3—La—O4—C23 | −162.7 (4) | C8—O2—C3—C4 | −0.7 (7) |
O14—La—O4—C23 | −84.9 (4) | La—O2—C3—C4 | 173.1 (3) |
O5'—La—O4—C23 | −122.3 (8) | C8—O2—C3—C2 | 178.7 (5) |
O5—La—O4—C23 | −117.0 (9) | La—O2—C3—C2 | −7.5 (4) |
O11—La—O4—C23 | 70.7 (4) | O1—C2—C3—O2 | −1.7 (4) |
O8—La—O4—C23 | 104.8 (4) | C1—C2—C3—O2 | 178.4 (3) |
O12—La—O4—C23 | 121.0 (4) | O1—C2—C3—C4 | 177.8 (3) |
O9—La—O4—C23 | 36.3 (4) | C1—C2—C3—C4 | −2.2 (5) |
O6—La—O4—C23 | −174.2 (4) | O2—C3—C4—C5 | 180.0 (4) |
O2—La—O4—C23 | −37.9 (4) | C2—C3—C4—C5 | 0.6 (6) |
O1—La—O5—N3 | −178.7 (6) | C3—C4—C5—C6 | −0.1 (8) |
O3—La—O5—N3 | −31.2 (9) | C4—C5—C6—C1 | 1.2 (8) |
O14—La—O5—N3 | −100.7 (8) | C7—C1—C6—C5 | 176.9 (5) |
O5'—La—O5—N3 | −56 (3) | C2—C1—C6—C5 | −2.8 (7) |
O11—La—O5—N3 | 99.4 (8) | C9—N1—C7—C1 | −178.2 (4) |
O8—La—O5—N3 | 79.4 (8) | C2—C1—C7—N1 | 7.1 (6) |
O12—La—O5—N3 | 38.7 (10) | C6—C1—C7—N1 | −172.6 (4) |
O9—La—O5—N3 | 129.3 (9) | C7—N1—C9—C10 | −168.9 (4) |
O6—La—O5—N3 | 7.2 (5) | C7—N1—C9—C14 | 11.1 (6) |
O4—La—O5—N3 | −69.8 (13) | C14—C9—C10—C11 | 1.5 (6) |
O2—La—O5—N3 | −163.3 (10) | N1—C9—C10—C11 | −178.6 (4) |
O1—La—O5'—N3 | 153.7 (9) | C9—C10—C11—C12 | −0.3 (7) |
O3—La—O5'—N3 | −67.7 (11) | C10—C11—C12—C13 | −1.5 (7) |
O14—La—O5'—N3 | −139.6 (12) | C10—C11—C12—C15 | 177.6 (5) |
O5—La—O5'—N3 | 88 (3) | C11—C12—C13—C14 | 2.2 (7) |
O11—La—O5'—N3 | 52.1 (17) | C15—C12—C13—C14 | −176.9 (5) |
O8—La—O5'—N3 | 46.0 (10) | C12—C13—C14—C9 | −1.1 (7) |
O12—La—O5'—N3 | −7.9 (13) | C10—C9—C14—C13 | −0.8 (6) |
O9—La—O5'—N3 | 92.7 (11) | N1—C9—C14—C13 | 179.2 (4) |
O6—La—O5'—N3 | −14.2 (7) | La—O3—C17—C16 | −174.5 (2) |
O4—La—O5'—N3 | −101.8 (11) | La—O3—C17—C18 | 6.2 (4) |
O2—La—O5'—N3 | 153.8 (12) | C22—C16—C17—O3 | −4.4 (5) |
O1—La—O6—N3 | −28.9 (6) | C21—C16—C17—O3 | 177.4 (3) |
O3—La—O6—N3 | 127.9 (3) | C22—C16—C17—C18 | 175.0 (3) |
O14—La—O6—N3 | 64.2 (3) | C21—C16—C17—C18 | −3.2 (4) |
O5'—La—O6—N3 | 13.1 (6) | C23—O4—C18—C19 | −16.6 (6) |
O5—La—O6—N3 | −8.0 (5) | La—O4—C18—C19 | 172.7 (3) |
O11—La—O6—N3 | −135.9 (3) | C23—O4—C18—C17 | 163.4 (4) |
O8—La—O6—N3 | −93.5 (3) | La—O4—C18—C17 | −7.2 (4) |
O12—La—O6—N3 | −161.7 (3) | O3—C17—C18—C19 | −178.1 (3) |
O9—La—O6—N3 | −61.4 (3) | C16—C17—C18—C19 | 2.5 (5) |
O4—La—O6—N3 | 139.1 (3) | O3—C17—C18—O4 | 1.8 (4) |
O2—La—O6—N3 | 1.0 (3) | C16—C17—C18—O4 | −177.6 (3) |
O1—La—O8—N4 | −33.1 (3) | O4—C18—C19—C20 | 179.8 (3) |
O3—La—O8—N4 | 171.8 (2) | C17—C18—C19—C20 | −0.3 (6) |
O14—La—O8—N4 | 80.2 (3) | C18—C19—C20—C21 | −1.2 (6) |
O5'—La—O8—N4 | 91.4 (5) | C19—C20—C21—C16 | 0.4 (6) |
O5—La—O8—N4 | 80.2 (5) | C22—C16—C21—C20 | −176.3 (3) |
O11—La—O8—N4 | −85.5 (3) | C17—C16—C21—C20 | 1.9 (5) |
O12—La—O8—N4 | −136.4 (3) | C24—N2—C22—C16 | −175.9 (3) |
O9—La—O8—N4 | −1.0 (2) | C21—C16—C22—N2 | −179.3 (3) |
O6—La—O8—N4 | 132.6 (3) | C17—C16—C22—N2 | 2.5 (5) |
O4—La—O8—N4 | −119.8 (2) | C22—N2—C24—C25 | 175.6 (4) |
O2—La—O8—N4 | 25.9 (3) | C22—N2—C24—C29 | −2.3 (6) |
O1—La—O9—N4 | 148.8 (3) | C29—C24—C25—C26 | −0.4 (7) |
O3—La—O9—N4 | −17.0 (4) | N2—C24—C25—C26 | −178.4 (4) |
O14—La—O9—N4 | −144.7 (2) | C24—C25—C26—C27 | 0.5 (8) |
O5'—La—O9—N4 | −80.7 (5) | C25—C26—C27—C28 | 0.1 (8) |
O5—La—O9—N4 | −79.2 (5) | C25—C26—C27—C30 | 179.3 (5) |
O11—La—O9—N4 | 80.0 (2) | C26—C27—C28—C29 | −0.7 (9) |
O8—La—O9—N4 | 1.1 (2) | C30—C27—C28—C29 | −179.9 (6) |
O12—La—O9—N4 | 42.1 (3) | C25—C24—C29—C28 | −0.2 (8) |
O6—La—O9—N4 | −39.7 (3) | N2—C24—C29—C28 | 177.6 (5) |
O4—La—O9—N4 | 114.1 (2) | C27—C28—C29—C24 | 0.8 (9) |
O2—La—O9—N4 | −148.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.86 | 2.01 | 2.668 (3) | 132 |
N1—H1A···O11 | 0.86 | 2.52 | 3.307 (4) | 153 |
N2—H2A···O3 | 0.86 | 1.95 | 2.627 (3) | 135 |
N2—H2A···O6 | 0.86 | 2.65 | 3.440 (5) | 154 |
Experimental details
Crystal data | |
Chemical formula | [La(NO3)3(C15H15NO2)2(CH4O)] |
Mr | 839.54 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 7.8616 (2), 14.6502 (5), 16.6470 (5) |
α, β, γ (°) | 73.210 (2), 85.648 (2), 79.320 (1) |
V (Å3) | 1803.26 (9) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.26 |
Crystal size (mm) | 0.43 × 0.31 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.634, 0.783 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 30011, 8464, 7465 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.654 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.101, 1.08 |
No. of reflections | 8464 |
No. of parameters | 473 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 1.23, −0.51 |
Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···O1 | 0.86 | 2.01 | 2.668 (3) | 132.2 |
N1—H1A···O11 | 0.86 | 2.52 | 3.307 (4) | 153.2 |
N2—H2A···O3 | 0.86 | 1.95 | 2.627 (3) | 134.8 |
N2—H2A···O6 | 0.86 | 2.65 | 3.440 (5) | 153.7 |
Schiff base ligands derived from substituted o-vanillin and aniline and their rare earth metal complexes have generated considerable attention in the past decades, due to their intriguing novel structural features (Burrows & Bailar, 1966; Zhao et al., 2007; Xian et al., 2008; Li et al., 2008) and promising applications in various fields such as catalysis, optoelectronic devices, and so on (Leadbeater & Marco, 2002; Quici et al., 2004). Interested in this field, we have been engaged in a major effort directed toward the synthesis of new analogous Schiff base derived from o-vanillin and their rare metal complexes. In few previous articles, we have reported our partial research results (Zhao et al., 2007; Xian et al., 2008; Li et al., 2008). Herein, we describe a new La(III) complex.
The single-crystal structure is shown in Fig. 1, which illustrates that the La(III) ion in this complex is eleven-coordinated by six O atoms from three nitrate radical ions, four O atoms from the Schiff bases, and one O atom from methanol. The Schiff bases are coordinated to the La(III) ion in the bidentate mode, using O atoms from methoxy groups and deprotonated phenolic hydroxyl groups. The bonds between La(III) and O atoms from phenoxy groups are 2.429 (2) and 2.482 (2) Å, which are shorter than those between La(III) and O atoms of methoxy groups [2.808 (2) and 2.964 (3) Å]. The nitrate radical anions coordinate to the La(III) with O atoms with the distances ranging from 2.574 (19) to 2.741 (3) Å, which are intermediate between the La—O(phenolic) and the La—O(methoxy) bond lengths. The La—O(methanol) bong length is only slightly longer than the La—O(phenolic). In addition, the O5 atom in a nitrate anion is disordered over two sites.
The hydrogen bonds and π···π weak non-covalent interactions give stability to the crystal structure. In each HL ligand, the proton of phenolic hydroxyl group is transferred to the imine N atom, which is involved in the formation of intramolecular hydrogen bonds. There are no classic hydrogen bonds between the adjacent molecules. π···π interactions exist in the crystal between symmetry-related molecules.