Tetra­kis(μ-2-pyridyloxyacetato)bis­[(1,10-phenanthroline)(2-pyridyloxyacetato)lanthanum(III)]

Liu, T.; Wang, Z.-W.; Wang, Y.-X.; Xie, Z.-P.

doi:10.1107/S1600536807030917

Retracted: Tetrakis(μ-2-pyridyloxyacetato)bis[(1,10-phenanthroline)(2-pyridyloxyacetato)lanthanum(III)]

T. Liu, Z.-W. Wang, Y.-X. Wang and Z.-P. Xie

The molecule of the title compound, [La₂(C₇H₆NO₃)₆(C₁₂H₈N₂)₂], has an inversion centre midway between the two La^III ions, which are bridged by two terdentate and two bidentate carboxylate groups. Each La atom is seven-coordinated by two N atoms of a 1,10-phenanthroline ligand and five O atoms of 2-pyridyloxyacetate ligands. In the crystal structure, intermolecular C—H

O hydrogen bonds lead to a supramolecular network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030917/hk2279sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030917/hk2279Isup2.hkl Contains datablock I

CCDC reference: 1277970

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.010 Å
R factor = 0.039
wR factor = 0.099
Data-to-parameter ratio = 18.8

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_B Check Low       Ueq as Compared to Neighbors for         O7

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.97 Ratio
PLAT220_ALERT_2_C Large Non-Solvent    N     Ueq(max)/Ueq(min) ...       2.63 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N5
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C22
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C29
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      83.00 A   3 

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for La1         (3)       3.11
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          3

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

There has been great interest in the design and synthesis of supramolecular metal organic frameworks with organic ligands and rare earth metals exhibiting novel properties such as optical, electronic, magnetic and biological (Swiegers & Malefetse, 2002; Johnson & Raymond, 2001; Hof et al., 2002; Tsukube & Shinoda, 2002; Zhang et al., 2005). In the synthesis of supramolecular metal organic frameworks by design, the assembly of molecular units in predefined arrangements is a key goal (Desiraju, 1997; Braga et al., 1998). Directional intermolecular interactions are the primary tools in achieving this goal and hydrogen bonding is currently the best tool amongst them (Zaworotko, 1997; Braga & Grepioni, 2000). These compounds are usually prepared by the reaction of rare-earth metal ions with bi- or multidentate ligands (Kay et al., 1972; Ma et al., 1999; Mao et al., 1998). We report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). It has an inversion centre between the two La^III ions, in which they are bridged by the two terdentate and the two bidentate carboxylate groups. Each La atom is seven-coordinated by the two N atoms of 1,10-phenanthroline (phen) ligand and the five O atoms of 2-pyridyloxyacetic acid ligands (Table 1). The La—O and La—N bonds are in the range of [2.457 (3)–2.887 (3) Å] and [2.739 (3)–2.769 (3) Å], respectively.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 2) lead to a supramolecular network structure (Fig. 2), in which they may be effective in the stabilization of the structure.

Related literature top

For bond length data, see: Allen et al. (1987). For related literature, see: Braga & Grepioni (2000); Braga et al. (1998); Desiraju (1997); Hof et al. (2002); Johnson & Raymond (2001); Kay et al. (1972); Ma et al. (1999); Mao et al. (1998); Swiegers & Malefetse (2002); Tsukube & Shinoda (2002); Zaworotko (1997); Zhang et al. (2005).

Experimental top

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb. Lanthanum (III) chloride hexahydrate (143 mg, 0.4 mmol), phen (79.2 mg, 0.4 mmol), phenoxyacetic acid (182.6 mg, 1.2 mmol) and distilled water (6 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure for 7 d at 433 K and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colorless solution was decanted from small colorless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

Structure description top

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level [symmetry code (A): 2 - x, -y, 2 - z].
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

Tetrakis(µ-2-pyridyloxyacetato)bis[(1,10-phenanthroline)(2- pyridyloxyacetato)lanthanum(III)] top

Crystal data top

[La₂(C₇H₆NO₃)₆(C₁₂H₈N₂)₂]	F(000) = 1552
M_r = 1551.00	D_x = 1.456 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9025 reflections
a = 20.312 (3) Å	θ = 2.4–26.7°
b = 8.721 (2) Å	µ = 1.27 mm⁻¹
c = 20.915 (3) Å	T = 273 K
β = 107.332 (9)°	Plate, colorless
V = 3536.8 (11) Å³	0.33 × 0.13 × 0.08 mm
Z = 2

Data collection top

Bruker SMART CCD area-detector diffractometer	7585 independent reflections
Radiation source: fine-focus sealed tube	5008 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
φ and ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→25
T_min = 0.682, T_max = 0.905	k = −10→11
27369 measured reflections	l = −26→26

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.05P)² + 0.9707P] where P = (F_o² + 2F_c²)/3
7585 reflections	(Δ/σ)_max = 0.001
403 parameters	Δρ_max = 0.59 e Å⁻³
3 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

[La₂(C₇H₆NO₃)₆(C₁₂H₈N₂)₂]	V = 3536.8 (11) Å³
M_r = 1551.00	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 20.312 (3) Å	µ = 1.27 mm⁻¹
b = 8.721 (2) Å	T = 273 K
c = 20.915 (3) Å	0.33 × 0.13 × 0.08 mm
β = 107.332 (9)°

Data collection top

Bruker SMART CCD area-detector diffractometer	7585 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5008 reflections with I > 2σ(I)
T_min = 0.682, T_max = 0.905	R_int = 0.043
27369 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	3 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.00	Δρ_max = 0.59 e Å⁻³
7585 reflections	Δρ_min = −0.59 e Å⁻³
403 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
La1	0.931204 (11)	0.19063 (2)	0.964291 (10)	0.04055 (9)
O1	0.84640 (13)	−0.0360 (3)	0.91884 (13)	0.0525 (7)
O2	0.94651 (13)	−0.1380 (4)	0.97709 (13)	0.0578 (7)
O3	0.94005 (14)	0.4208 (3)	1.03412 (12)	0.0560 (7)
O4	0.97065 (14)	0.0599 (3)	0.87485 (12)	0.0558 (7)
O5	1.06702 (14)	−0.0831 (3)	0.92168 (13)	0.0577 (7)
O6	1.11841 (16)	−0.0166 (4)	0.82197 (15)	0.0765 (9)
O7	0.78448 (16)	−0.3265 (3)	0.89795 (17)	0.0721 (9)
O8	1.00778 (16)	0.6128 (4)	1.09096 (13)	0.0656 (8)
O9	0.98699 (16)	0.5278 (4)	1.20622 (13)	0.0711 (9)
N1	0.79696 (17)	0.2345 (4)	0.96667 (17)	0.0554 (9)
N2	0.83402 (19)	0.3068 (4)	0.85441 (16)	0.0557 (9)
N3	1.1133 (3)	0.1077 (7)	0.7156 (3)	0.129 (2)
N4	0.7868 (4)	−0.2775 (7)	1.0123 (4)	0.1454 (13)
N5	0.9271 (3)	0.3777 (7)	1.2705 (2)	0.1130 (17)
C1	0.7780 (2)	0.1921 (5)	1.0201 (2)	0.0710 (13)
H1	0.8122	0.1690	1.0597	0.085*
C2	0.7091 (3)	0.1811 (7)	1.0189 (3)	0.0924 (18)
H2	0.6981	0.1515	1.0572	0.111*
C3	0.6578 (3)	0.2138 (8)	0.9613 (4)	0.101 (2)
H3	0.6118	0.2060	0.9603	0.122*
C4	0.6742 (3)	0.2588 (7)	0.9043 (3)	0.0846 (16)
C5	0.7460 (2)	0.2676 (5)	0.9088 (2)	0.0595 (11)
C6	0.6238 (3)	0.2977 (9)	0.8398 (4)	0.120 (3)
H6	0.5770	0.2888	0.8354	0.144*
C7	0.6427 (3)	0.3450 (8)	0.7875 (3)	0.112 (2)
H7	0.6090	0.3726	0.7482	0.135*
C8	0.7133 (3)	0.3542 (6)	0.7904 (3)	0.0787 (15)
C9	0.7658 (2)	0.3096 (5)	0.8505 (2)	0.0588 (11)
C10	0.7356 (4)	0.4030 (7)	0.7365 (3)	0.0950 (19)
H10	0.7034	0.4371	0.6975	0.114*
C11	0.8032 (4)	0.4012 (6)	0.7407 (2)	0.0903 (17)
H11	0.8177	0.4336	0.7046	0.108*
C12	0.8524 (3)	0.3489 (5)	0.8009 (2)	0.0711 (13)
H12	0.8987	0.3441	0.8028	0.085*
C13	0.8843 (2)	−0.1512 (5)	0.93930 (19)	0.0505 (10)
C14	0.8576 (2)	−0.3145 (5)	0.9191 (2)	0.0623 (11)
H14A	0.8749	−0.3490	0.8830	0.075*
H14B	0.8761	−0.3824	0.9569	0.075*
C15	0.7509 (6)	−0.3132 (8)	0.9433 (5)	0.1454 (13)
C16	0.6798 (5)	−0.3380 (8)	0.9209 (5)	0.1454 (13)
H16	0.6584	−0.3580	0.8758	0.174*
C17	0.6412 (5)	−0.3333 (8)	0.9649 (5)	0.1454 (13)
H17	0.5945	−0.3582	0.9510	0.174*
C18	0.6736 (5)	−0.2903 (8)	1.0307 (5)	0.1454 (13)
H18	0.6464	−0.2789	1.0591	0.174*
C19	0.7428 (5)	−0.2636 (9)	1.0565 (5)	0.1454 (13)
H19	0.7616	−0.2371	1.1013	0.174*
C20	0.9691 (2)	0.4992 (5)	1.08642 (19)	0.0505 (10)
C21	0.9490 (2)	0.4459 (5)	1.14740 (19)	0.0650 (12)
H21A	0.9000	0.4623	1.1397	0.078*
H21B	0.9581	0.3370	1.1541	0.078*
C22	0.9751 (2)	0.4892 (5)	1.2657 (2)	0.0617 (11)
C23	1.0144 (3)	0.5693 (6)	1.3220 (2)	0.0795 (15)
H23	1.0469	0.6408	1.3180	0.095*
C24	1.0047 (3)	0.5416 (8)	1.3834 (2)	0.1020 (19)
H24	1.0304	0.5954	1.4210	0.122*
C25	0.9566 (4)	0.4332 (9)	1.3894 (3)	0.115 (2)
H25	0.9494	0.4167	1.4308	0.138*
C26	0.9201 (4)	0.3518 (9)	1.3352 (3)	0.119 (3)
H26	0.8895	0.2768	1.3405	0.142*
C27	1.0287 (2)	0.0032 (5)	0.87717 (19)	0.0491 (9)
C28	1.0526 (2)	0.0503 (5)	0.8173 (2)	0.0637 (12)
H28B	1.0190	0.0170	0.7761	0.076*
H28A	1.0560	0.1611	0.8159	0.076*
C29	1.1458 (3)	0.0143 (6)	0.7707 (2)	0.0697 (13)
C30	1.2082 (3)	−0.0548 (7)	0.7764 (3)	0.0895 (16)
H30	1.2292	−0.1148	0.8136	0.107*
C31	1.2398 (3)	−0.0351 (8)	0.7264 (4)	0.106 (2)
H31	1.2817	−0.0831	0.7300	0.127*
C32	1.2096 (4)	0.0547 (8)	0.6720 (4)	0.114 (2)
H32	1.2312	0.0679	0.6389	0.136*
C33	1.1486 (4)	0.1242 (8)	0.6661 (3)	0.119 (2)
H33	1.1290	0.1847	0.6286	0.142*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
La1	0.04671 (13)	0.03586 (13)	0.03402 (12)	−0.00164 (11)	0.00427 (8)	0.00055 (10)
O1	0.0531 (15)	0.0420 (17)	0.0535 (16)	0.0007 (13)	0.0023 (12)	−0.0036 (12)
O2	0.0511 (17)	0.0636 (19)	0.0493 (16)	−0.0041 (13)	0.0005 (13)	0.0072 (13)
O3	0.0775 (19)	0.0429 (16)	0.0449 (15)	−0.0070 (15)	0.0142 (13)	−0.0061 (13)
O4	0.0648 (18)	0.0573 (18)	0.0446 (15)	0.0085 (15)	0.0152 (13)	0.0023 (13)
O5	0.0684 (18)	0.0585 (19)	0.0466 (16)	0.0088 (15)	0.0178 (13)	0.0117 (14)
O6	0.077 (2)	0.096 (3)	0.064 (2)	0.0207 (19)	0.0335 (17)	0.0231 (18)
O7	0.067 (2)	0.055 (2)	0.079 (2)	−0.0157 (15)	−0.0016 (16)	−0.0073 (16)
O8	0.094 (2)	0.0575 (19)	0.0445 (16)	−0.0287 (18)	0.0195 (15)	−0.0028 (14)
O9	0.099 (2)	0.072 (2)	0.0426 (16)	−0.0303 (18)	0.0207 (15)	−0.0074 (14)
N1	0.055 (2)	0.051 (2)	0.053 (2)	0.0033 (16)	0.0047 (17)	−0.0081 (16)
N2	0.069 (2)	0.045 (2)	0.0430 (19)	0.0038 (17)	0.0015 (16)	0.0007 (16)
N3	0.166 (5)	0.136 (5)	0.106 (4)	−0.003 (4)	0.075 (4)	0.026 (4)
N4	0.171 (4)	0.110 (2)	0.186 (4)	0.018 (2)	0.100 (3)	0.030 (3)
N5	0.117 (4)	0.135 (5)	0.096 (4)	−0.033 (4)	0.046 (3)	0.008 (3)
C1	0.065 (3)	0.087 (4)	0.060 (3)	0.007 (3)	0.017 (2)	−0.003 (3)
C2	0.066 (3)	0.129 (5)	0.088 (4)	0.004 (3)	0.033 (3)	−0.014 (4)
C3	0.052 (3)	0.133 (6)	0.116 (5)	−0.002 (3)	0.020 (3)	−0.019 (4)
C4	0.052 (3)	0.097 (4)	0.085 (4)	0.008 (3)	−0.008 (3)	−0.021 (3)
C5	0.056 (3)	0.047 (3)	0.066 (3)	0.006 (2)	0.004 (2)	−0.011 (2)
C6	0.064 (4)	0.159 (8)	0.111 (5)	0.015 (4)	−0.012 (4)	−0.032 (5)
C7	0.082 (4)	0.128 (6)	0.090 (5)	0.041 (4)	−0.030 (3)	−0.018 (4)
C8	0.082 (4)	0.070 (3)	0.059 (3)	0.018 (3)	−0.018 (3)	−0.011 (2)
C9	0.064 (3)	0.042 (2)	0.052 (2)	0.005 (2)	−0.0114 (19)	−0.005 (2)
C10	0.118 (5)	0.082 (4)	0.055 (3)	0.020 (4)	−0.021 (3)	0.002 (3)
C11	0.130 (5)	0.081 (4)	0.044 (3)	0.001 (4)	0.001 (3)	0.012 (3)
C12	0.092 (4)	0.062 (3)	0.050 (3)	−0.003 (3)	0.006 (2)	0.009 (2)
C13	0.054 (2)	0.056 (3)	0.037 (2)	−0.003 (2)	0.0061 (17)	−0.0027 (18)
C14	0.067 (3)	0.051 (3)	0.062 (3)	0.004 (2)	0.007 (2)	−0.006 (2)
C15	0.171 (4)	0.110 (2)	0.186 (4)	0.018 (2)	0.100 (3)	0.030 (3)
C16	0.171 (4)	0.110 (2)	0.186 (4)	0.018 (2)	0.100 (3)	0.030 (3)
C17	0.171 (4)	0.110 (2)	0.186 (4)	0.018 (2)	0.100 (3)	0.030 (3)
C18	0.171 (4)	0.110 (2)	0.186 (4)	0.018 (2)	0.100 (3)	0.030 (3)
C19	0.171 (4)	0.110 (2)	0.186 (4)	0.018 (2)	0.100 (3)	0.030 (3)
C20	0.067 (3)	0.039 (2)	0.045 (2)	−0.004 (2)	0.0145 (19)	0.0012 (18)
C21	0.084 (3)	0.063 (3)	0.049 (2)	−0.021 (3)	0.021 (2)	−0.006 (2)
C22	0.078 (3)	0.063 (3)	0.045 (2)	−0.007 (2)	0.021 (2)	0.004 (2)
C23	0.098 (4)	0.086 (4)	0.052 (3)	−0.024 (3)	0.017 (2)	−0.010 (3)
C24	0.130 (5)	0.121 (5)	0.047 (3)	−0.024 (4)	0.013 (3)	−0.010 (3)
C25	0.144 (6)	0.154 (7)	0.057 (3)	−0.032 (5)	0.043 (4)	0.008 (4)
C26	0.140 (6)	0.160 (7)	0.067 (4)	−0.067 (5)	0.048 (4)	−0.002 (4)
C27	0.061 (3)	0.042 (2)	0.043 (2)	−0.003 (2)	0.0134 (19)	−0.0015 (18)
C28	0.073 (3)	0.065 (3)	0.055 (3)	0.007 (2)	0.023 (2)	0.014 (2)
C29	0.081 (3)	0.075 (3)	0.063 (3)	−0.004 (3)	0.038 (3)	0.005 (2)
C30	0.090 (4)	0.110 (5)	0.081 (4)	0.002 (4)	0.044 (3)	0.002 (3)
C31	0.101 (4)	0.114 (6)	0.126 (5)	−0.005 (4)	0.069 (4)	−0.009 (4)
C32	0.152 (6)	0.096 (5)	0.131 (6)	−0.015 (5)	0.100 (5)	0.001 (4)
C33	0.169 (7)	0.117 (5)	0.103 (5)	0.016 (5)	0.091 (5)	0.033 (4)

Geometric parameters (Å, º) top

La1—O1	2.608 (3)	C6—H6	0.9300
La1—O2	2.887 (3)	C7—C8	1.420 (9)
La1—O3	2.457 (3)	C7—H7	0.9300
La1—O4	2.517 (3)	C8—C10	1.400 (8)
La1—N1	2.769 (3)	C8—C9	1.438 (6)
La1—N2	2.739 (3)	C10—C11	1.351 (8)
La1—O2ⁱ	2.463 (3)	C10—H10	0.9300
La1—O5ⁱ	2.553 (3)	C11—C12	1.429 (6)
La1—O8ⁱⁱ	2.581 (3)	C11—H11	0.9300
O1—C13	1.260 (5)	C12—H12	0.9300
O2—C13	1.280 (5)	C13—C14	1.538 (6)
O2—La1ⁱ	2.463 (3)	C14—H14A	0.9700
O3—C20	1.276 (4)	C14—H14B	0.9700
O4—C27	1.266 (4)	C15—C16	1.396 (12)
O5—C27	1.268 (4)	C16—C17	1.377 (10)
O5—La1ⁱ	2.553 (3)	C16—H16	0.9300
O6—C29	1.373 (5)	C17—C18	1.388 (12)
O6—C28	1.435 (5)	C17—H17	0.9300
O7—C15	1.329 (9)	C18—C19	1.366 (11)
O7—C14	1.422 (5)	C18—H18	0.9300
O8—C20	1.251 (5)	C19—H19	0.9300
O8—La1ⁱⁱ	2.581 (3)	C20—C21	1.523 (5)
O9—C22	1.377 (5)	C21—H21A	0.9700
O9—C21	1.433 (5)	C21—H21B	0.9700
N1—C1	1.338 (5)	C22—C23	1.397 (6)
N1—C5	1.369 (5)	C23—C24	1.378 (7)
N2—C12	1.333 (5)	C23—H23	0.9300
N2—C9	1.363 (6)	C24—C25	1.393 (8)
N3—C29	1.406 (7)	C24—H24	0.9300
N3—C33	1.432 (7)	C25—C26	1.357 (8)
N4—C15	1.444 (11)	C25—H25	0.9300
N4—C19	1.470 (9)	C26—H26	0.9300
N5—C22	1.403 (6)	C27—C28	1.529 (5)
N5—C26	1.420 (7)	C28—H28B	0.9700
C1—C2	1.396 (7)	C28—H28A	0.9700
C1—H1	0.9300	C29—C30	1.376 (7)
C2—C3	1.370 (8)	C30—C31	1.391 (7)
C2—H2	0.9300	C30—H30	0.9300
C3—C4	1.387 (8)	C31—C32	1.366 (9)
C3—H3	0.9300	C31—H31	0.9300
C4—C5	1.436 (7)	C32—C33	1.351 (9)
C4—C6	1.470 (8)	C32—H32	0.9300
C5—C9	1.441 (6)	C33—H33	0.9300
C6—C7	1.328 (9)

O1—La1—O2	47.35 (8)	C8—C9—C5	119.1 (5)
O1—La1—O3	139.39 (9)	C11—C10—C8	120.8 (5)
O1—La1—O4	73.00 (9)	C11—C10—H10	119.6
O2—La1—O3	140.28 (8)	C8—C10—H10	119.6
O2—La1—O4	64.52 (8)	C10—C11—C12	119.4 (5)
O3—La1—O4	145.97 (9)	C10—C11—H11	120.3
O1—La1—N1	64.18 (9)	C12—C11—H11	120.3
O2—La1—N1	102.42 (9)	N2—C12—C11	122.0 (5)
O3—La1—N1	76.96 (10)	N2—C12—H12	119.0
O4—La1—N1	127.54 (9)	C11—C12—H12	119.0
O1—La1—N2	75.05 (9)	O1—C13—O2	121.9 (4)
O2—La1—N2	118.42 (8)	O1—C13—C14	121.0 (4)
O3—La1—N2	95.92 (9)	O2—C13—C14	117.1 (4)
O4—La1—N2	81.57 (9)	O7—C14—C13	113.8 (3)
N1—La1—N2	59.76 (11)	O7—C14—H14A	108.8
O3—La1—O2ⁱ	88.40 (10)	C13—C14—H14A	108.8
O2ⁱ—La1—O4	77.79 (9)	O7—C14—H14B	108.8
O3—La1—O5ⁱ	76.50 (9)	C13—C14—H14B	108.8
O2ⁱ—La1—O5ⁱ	74.64 (9)	H14A—C14—H14B	107.7
O4—La1—O5ⁱ	127.51 (9)	O7—C15—C16	116.5 (10)
O3—La1—O8ⁱⁱ	76.33 (9)	O7—C15—N4	121.3 (9)
O2ⁱ—La1—O8ⁱⁱ	78.41 (10)	C16—C15—N4	122.2 (8)
O4—La1—O8ⁱⁱ	70.52 (9)	C17—C16—C15	120.7 (10)
O5ⁱ—La1—O8ⁱⁱ	141.91 (9)	C17—C16—H16	119.7
O2ⁱ—La1—O1	119.91 (10)	C15—C16—H16	119.7
O5ⁱ—La1—O1	83.46 (9)	C16—C17—C18	118.2 (10)
O8ⁱⁱ—La1—O1	133.88 (8)	C16—C17—H17	120.9
O2ⁱ—La1—N2	148.68 (10)	C18—C17—H17	120.9
O5ⁱ—La1—N2	136.54 (10)	C19—C18—C17	124.6 (9)
O8ⁱⁱ—La1—N2	72.59 (10)	C19—C18—H18	117.7
O2ⁱ—La1—N1	150.37 (10)	C17—C18—H18	117.7
O5ⁱ—La1—N1	76.93 (10)	C18—C19—N4	118.9 (9)
O8ⁱⁱ—La1—N1	121.53 (11)	C18—C19—H19	120.5
O2ⁱ—La1—O2	72.79 (10)	N4—C19—H19	120.5
O5ⁱ—La1—O2	65.01 (8)	O8—C20—O3	127.5 (4)
O8ⁱⁱ—La1—O2	130.39 (9)	O8—C20—C21	119.8 (4)
C13—O1—La1	102.1 (2)	O3—C20—C21	112.6 (3)
C13—O2—La1ⁱ	162.5 (3)	O9—C21—C20	110.9 (3)
C13—O2—La1	88.4 (2)	O9—C21—H21A	109.5
La1ⁱ—O2—La1	107.21 (10)	C20—C21—H21A	109.5
C20—O3—La1	151.7 (3)	O9—C21—H21B	109.5
C27—O4—La1	130.4 (2)	C20—C21—H21B	109.5
C27—O5—La1ⁱ	137.6 (3)	H21A—C21—H21B	108.0
C29—O6—C28	116.9 (3)	O9—C22—C23	115.4 (4)
C15—O7—C14	118.9 (6)	O9—C22—N5	123.2 (4)
C20—O8—La1ⁱⁱ	150.1 (3)	C23—C22—N5	121.4 (4)
C22—O9—C21	117.3 (3)	C24—C23—C22	119.6 (5)
C1—N1—C5	117.9 (4)	C24—C23—H23	120.2
C1—N1—La1	120.4 (3)	C22—C23—H23	120.2
C5—N1—La1	120.1 (3)	C23—C24—C25	120.2 (5)
C12—N2—C9	118.6 (4)	C23—C24—H24	119.9
C12—N2—La1	119.6 (3)	C25—C24—H24	119.9
C9—N2—La1	121.5 (3)	C26—C25—C24	120.2 (5)
C29—N3—C33	116.0 (6)	C26—C25—H25	119.9
C15—N4—C19	115.2 (8)	C24—C25—H25	119.9
C22—N5—C26	116.7 (5)	C25—C26—N5	121.9 (6)
N1—C1—C2	122.7 (5)	C25—C26—H26	119.1
N1—C1—H1	118.6	N5—C26—H26	119.1
C2—C1—H1	118.6	O4—C27—O5	128.4 (4)
C3—C2—C1	119.9 (5)	O4—C27—C28	112.5 (3)
C3—C2—H2	120.1	O5—C27—C28	119.1 (4)
C1—C2—H2	120.1	O6—C28—C27	110.6 (3)
C2—C3—C4	120.1 (5)	O6—C28—H28B	109.5
C2—C3—H3	120.0	C27—C28—H28B	109.5
C4—C3—H3	120.0	O6—C28—H28A	109.5
C3—C4—C5	117.3 (5)	C27—C28—H28A	109.5
C3—C4—C6	125.0 (6)	H28B—C28—H28A	108.1
C5—C4—C6	117.7 (6)	O6—C29—C30	115.1 (4)
N1—C5—C4	122.1 (5)	O6—C29—N3	123.6 (5)
N1—C5—C9	118.3 (4)	C30—C29—N3	121.3 (5)
C4—C5—C9	119.5 (4)	C29—C30—C31	120.1 (6)
C7—C6—C4	122.3 (6)	C29—C30—H30	119.9
C7—C6—H6	118.8	C31—C30—H30	120.0
C4—C6—H6	118.8	C32—C31—C30	120.2 (6)
C6—C7—C8	121.2 (6)	C32—C31—H31	119.9
C6—C7—H7	119.4	C30—C31—H31	119.9
C8—C7—H7	119.4	C33—C32—C31	120.4 (6)
C10—C8—C7	123.2 (5)	C33—C32—H32	119.8
C10—C8—C9	116.8 (5)	C31—C32—H32	119.8
C7—C8—C9	120.0 (6)	C32—C33—N3	122.1 (6)
N2—C9—C8	122.3 (5)	C32—C33—H33	119.0
N2—C9—C5	118.6 (3)	N3—C33—H33	119.0

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱⁱⁱ	0.93	2.35	3.224 (6)	156
C14—H14B···O3^iv	0.97	2.45	3.394 (5)	165
C12—H12···O8ⁱⁱ	0.93	2.48	3.076 (6)	122
C1—H1···O5ⁱ	0.93	2.48	3.163 (6)	130

Symmetry codes: (i) −x+2, −y, −z+2; (ii) −x+2, −y+1, −z+2; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x, y−1, z.

Experimental details

Crystal data
Chemical formula	[La₂(C₇H₆NO₃)₆(C₁₂H₈N₂)₂]
M_r	1551.00
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	20.312 (3), 8.721 (2), 20.915 (3)
β (°)	107.332 (9)
V (Å³)	3536.8 (11)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.27
Crystal size (mm)	0.33 × 0.13 × 0.08

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.682, 0.905
No. of measured, independent and observed [I > 2σ(I)] reflections	27369, 7585, 5008
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.099, 1.00
No. of reflections	7585
No. of parameters	403
No. of restraints	3
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.59, −0.59

Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL.

Selected geometric parameters (Å, º) top

La1—O1	2.608 (3)	La1—O4	2.517 (3)
La1—O2	2.887 (3)	La1—N1	2.769 (3)
La1—O3	2.457 (3)	La1—N2	2.739 (3)

O1—La1—O2	47.35 (8)	O3—La1—N1	76.96 (10)
O1—La1—O3	139.39 (9)	O4—La1—N1	127.54 (9)
O1—La1—O4	73.00 (9)	O1—La1—N2	75.05 (9)
O2—La1—O3	140.28 (8)	O2—La1—N2	118.42 (8)
O2—La1—O4	64.52 (8)	O3—La1—N2	95.92 (9)
O3—La1—O4	145.97 (9)	O4—La1—N2	81.57 (9)
O1—La1—N1	64.18 (9)	N1—La1—N2	59.76 (11)
O2—La1—N1	102.42 (9)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O1ⁱ	0.93	2.35	3.224 (6)	156
C14—H14B···O3ⁱⁱ	0.97	2.45	3.394 (5)	165
C12—H12···O8ⁱⁱⁱ	0.93	2.48	3.076 (6)	122
C1—H1···O5^iv	0.93	2.48	3.163 (6)	130

Symmetry codes: (i) −x+3/2, y+1/2, −z+3/2; (ii) x, y−1, z; (iii) −x+2, −y+1, −z+2; (iv) −x+2, −y, −z+2.

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Retracted: Tetra­kis(μ-2-pyridyloxyacetato)bis­[(1,10-phenanthroline)(2-pyridyloxyacetato)lanthanum(III)]

Supporting information

Key indicators

checkCIF/PLATON results

Retracted: Tetrakis(μ-2-pyridyloxyacetato)bis[(1,10-phenanthroline)(2-pyridyloxyacetato)lanthanum(III)]