Hexa-μ-α-methyl­acrylato-bis­[(1,10-phenanthroline)lanthanum(III)] dihydrate

The title compound, [La₂(C₄H₅O₂)₆(C₁₂H₈N₂)₂]·2H₂O, is a discrete centrosymmetric homodinuclear complex, which is structurally very similar to a previously studied analogue. The La^III atoms are bridged by two bidentate and two tridentate carboxyl­ate groups, with an La...La separation of 4.0807 (4) Å. Each La^III atom exhibits a distorted tricapped trigonal prismatic coordination formed by seven O atoms of bridging methyl­acrylate groups and two N atoms of the bidentate chelating 1,10-phenanthroline ligands.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.009 Å
• R factor = 0.035
• wR factor = 0.112
• Data-to-parameter ratio = 17.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.82 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  La1    -   O6_a    ..       8.36 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O2
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        C42
PLAT342_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          9
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C24
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C33
PLAT415_ALERT_2_C Short Inter D-H..H-X       HW2    ..  H6      ..       2.14 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2
PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) .       1.15 Ratio
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          2
              H2 O

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

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

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S1. Comment

Molecular magnetic compounds, such as molecular ferro- and ferrimagnets, organic magnets, single-molecule magnets and high-spin molecules, have recently attracted attention (Miller & Drillon, 2001a,b, Miller & Drillon, 2002; Christou et al., 2000). Efforts to obtain molecular magnets containing rare-earth ions have been comparatively less numerous because the interactions between pairs of f electrons are expected to be small, producing measurable effects only at extremely low temperatures, but the number of new reported compounds in which rare-earth ions are magnetically coupled to transition-metal ions and/or organic radicals is rapidly increasing. In recent nears, we have pursued a project on the structures and properties of heteronuclear complexes of rare-earth and transition metals bridged by carboxyl groups (Wu et al., 2002, 2003, 2004; Zhu et al., 2005). The title complex, (I), was unexpectedly obtained during the preparation of a lanthanium–iron complex.

Fig. 1 shows the molecular structure of the title complex; selected bond distances are listed in Table 1.

Compound (I) is isostructural with another La analogue, (II), in which the water molecule is replaced by an α-methylacrylic acid molecule (Lu, et al., 1996). As one would expect, the surroundings of the central atoms in the two complexes are the same. This means that the La^III atoms, with the coordination geometry of a distorted tricapped trigonal prism, are linked to each other by bidentate and tridentate carboxylate groups to form a centrosymmetric dimeric unit. Each La^III atom is nine-coordinated by two N atoms of the phenanthroline ligand and seven O atoms from three different coordination modes of six carboxylate groups. The detailed coordination modes of α-methylacrylate groups in (II) are also fully applicable to the title complex. The La···Laⁱ separation [4.0807 (4) Å] in the dimer just exceeds the sum of two atomic radii and is slightly longer than that [4.0456 (4) Å] in (II).

The structure of the title complex has two distinct La—O distances; the average La—O_bridging bond length is 2.498 Å and La—O_chelating is 2.606 Å, which are similar to those (2.494 and 2.612 Å) of (II). The La—O_chelating distance is significantly larger than the sum of the covalent radii of the two atoms, as is to be expected because the (O—La—O)_chelating angles of about 50° indicate ring strain. The phenanthroline ligands possess local C_2v symmetry. The average La—N bond distance is 2.708 Å and is nearly the same as the corresponding La—N distance (2.709 Å) in (II). A water molecule is connected with atom O1 by a hydrogen bond.

Comparison of structures (I) and (II) shows that it is uncertain whether water or a free α-methylacrylic acid molecule will be included in the complex during the growth of the crystal.

S2. Experimental

LaL₃·2H₂O [430 mg, 1.0 mmol; HL = CH₂C(CH₃)COOH] was dissolved in water (5 ml). A 1 M solution of Fe(NO₃)₃ (1.0 ml) was added and the pH was adjusted to 4.1 with 0.1 M HL. An ethanol solution (5 ml) of 1,10-phenanthroline (200 mg, 1.0 mmol) was added to the mixture with stirring. The filtrate was allowed to stand at room temperature, and colourless single crystals suitable for X-ray work precipitated after a few days. Analysis calculated for C₄₈H₅₀La₂N₄O₁₄: C 49.41, H 4.15, N 4.80, La 23.81%; found: C 49.56, H 4.18, N 4.76, La 23.63%.

S3. Refinement

All H atoms were placed in calculated positions (C—H = 0.93–0.96 Å and O—H = 0.94–0.99 Å) and included in the final cycles of refinement in a riding model, with U_iso(H) = 1.2U_eq(C) [U_iso(H) = 1.5U_eq(C,O) in the case of the methyl and water H atoms].

Computing details

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: CrystalStructure (Rigaku/MSC, 2002); data reduction: CrystalStructure; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures

Fig. 1. Molecule of the title complex, with the displacement ellipsoids drawn at the 30% probability level. The H atoms have been omitted.

Hexa-µ-α-methylacrylato-bis[(1,10-phenanthroline)lanthanum(III)] monohydrate

Crystal data

[La2(C4H5O2)6(C12H8N2)2]·2H2O	Z = 1
Mr = 1184.74	F(000) = 592
Triclinic, P1	Dx = 1.619 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.8815 (4) Å	Cell parameters from 6732 reflections
b = 11.0081 (5) Å	θ = 2.5–27.5°
c = 11.7412 (7) Å	µ = 1.80 mm^−1
α = 69.229 (2)°	T = 293 K
β = 77.892 (4)°	Chunk, colourless
γ = 68.091 (2)°	0.21 × 0.18 × 0.14 mm
V = 1215.16 (10) Å^3

Data collection

Rigaku R-AXIS RAPID diffractometer	5471 independent reflections
Radiation source: fine-focus sealed tube	5112 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.045
Detector resolution: 10.0 pixels mm^-1	θmax = 27.5°, θmin = 1.9°
ω scans	h = −13→14
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −13→14
Tmin = 0.703, Tmax = 0.786	l = −15→15
11677 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H-atom parameters constrained
S = 1.24	w = 1/[σ^2(Fo^2) + (0.0611P)^2 + 0.7074P] where P = (Fo^2 + 2Fc^2)/3
5471 reflections	(Δ/σ)max = 0.001
307 parameters	Δρmax = 0.81 e Å^−3
0 restraints	Δρmin = −1.21 e Å^−3

Special details

Experimental. The elemental analyses on C, H and N were performed using a Carlo-Erba 1110 Elemental Analyzer; La was analyzed by titration with edta.

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 (Ų)

	x	y	z	Uiso*/Ueq
La1	0.856611 (19)	0.56341 (2)	0.629075 (19)	0.02779 (9)
O1	0.8829 (3)	0.3733 (3)	0.8378 (3)	0.0457 (8)
O2	0.6862 (3)	0.4584 (4)	0.7671 (3)	0.0489 (8)
O3	0.8836 (3)	0.8022 (3)	0.5132 (3)	0.0422 (7)
O4	0.7597 (3)	0.5913 (4)	0.4432 (3)	0.0438 (7)
O5	1.0851 (3)	0.5077 (4)	0.6836 (3)	0.0439 (7)
O6	0.9738 (3)	0.3565 (3)	0.5647 (3)	0.0375 (6)
O7	1.1319 (6)	0.1741 (7)	0.7938 (7)	0.115 (2)
HW1	1.0462	0.2464	0.8026	0.172*
HW2	1.1882	0.2231	0.7426	0.172*
N1	0.8041 (3)	0.6969 (4)	0.7961 (3)	0.0359 (7)
N2	0.6166 (3)	0.7603 (4)	0.6430 (3)	0.0368 (8)
C1	0.8901 (5)	0.6631 (5)	0.8752 (5)	0.0451 (10)
H1	0.9635	0.5840	0.8795	0.054*
C2	0.8778 (6)	0.7385 (6)	0.9527 (5)	0.0541 (13)
H2	0.9401	0.7092	1.0084	0.065*
C3	0.7720 (5)	0.8566 (6)	0.9452 (5)	0.0516 (12)
H3	0.7623	0.9098	0.9950	0.062*
C4	0.6786 (5)	0.8969 (5)	0.8624 (4)	0.0435 (10)
C5	0.5628 (6)	1.0196 (6)	0.8500 (5)	0.0533 (12)
H5	0.5534	1.0802	0.8922	0.064*
C6	0.4687 (5)	1.0465 (5)	0.7780 (5)	0.0524 (12)
H6	0.3940	1.1244	0.7730	0.063*
C7	0.4810 (4)	0.9589 (5)	0.7100 (4)	0.0419 (10)
C8	0.3811 (5)	0.9788 (6)	0.6393 (5)	0.0520 (12)
H8	0.3029	1.0529	0.6357	0.062*
C9	0.3983 (5)	0.8912 (6)	0.5770 (5)	0.0551 (13)
H9	0.3309	0.9022	0.5333	0.066*
C10	0.5185 (5)	0.7834 (5)	0.5786 (5)	0.0462 (11)
H10	0.5305	0.7254	0.5328	0.055*
C11	0.5972 (4)	0.8439 (4)	0.7101 (4)	0.0347 (8)
C12	0.6977 (4)	0.8124 (4)	0.7895 (4)	0.0343 (8)
C21	0.7637 (5)	0.3758 (5)	0.8480 (4)	0.0395 (9)
C22	0.7128 (6)	0.2818 (6)	0.9582 (5)	0.0533 (12)
C23	0.5765 (8)	0.3067 (9)	0.9799 (7)	0.097 (3)
H23A	0.5425	0.2482	1.0467	0.116*
H23B	0.5192	0.3818	0.9276	0.116*
C24	0.8082 (9)	0.1696 (8)	1.0330 (7)	0.094 (3)
H24A	0.8959	0.1728	1.0005	0.140*
H24B	0.8014	0.0846	1.0344	0.140*
H24C	0.7914	0.1759	1.1147	0.140*
C31	0.9857 (4)	0.7639 (4)	0.4459 (4)	0.0341 (8)
C32	1.0651 (5)	0.8577 (5)	0.3814 (4)	0.0421 (10)
C33	0.9912 (7)	1.0074 (6)	0.3431 (7)	0.0686 (17)
H33A	0.8976	1.0223	0.3637	0.103*
H33B	1.0079	1.0451	0.2563	0.103*
H33C	1.0202	1.0518	0.3845	0.103*
C34	1.1991 (6)	0.8026 (7)	0.3649 (7)	0.0661 (16)
H34A	1.2506	0.8597	0.3275	0.079*
H34B	1.2396	0.7077	0.3909	0.079*
C41	0.7965 (4)	0.5330 (4)	0.3618 (4)	0.0357 (9)
C42	0.6936 (5)	0.5094 (5)	0.3115 (5)	0.0450 (10)
C43	0.5669 (5)	0.5636 (7)	0.3435 (6)	0.0668 (17)
H43A	0.5028	0.5495	0.3130	0.080*
H43B	0.5414	0.6161	0.3967	0.080*
C44	0.7420 (7)	0.4241 (9)	0.2268 (8)	0.084 (2)
H44A	0.8374	0.3937	0.2166	0.126*
H44B	0.7077	0.4779	0.1488	0.126*
H44C	0.7121	0.3456	0.2603	0.126*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
La1	0.02322 (12)	0.03225 (13)	0.02808 (13)	−0.00983 (9)	−0.00116 (8)	−0.00921 (9)
O1	0.0392 (17)	0.0472 (17)	0.0439 (18)	−0.0183 (14)	−0.0075 (13)	0.0005 (14)
O2	0.0365 (17)	0.057 (2)	0.048 (2)	−0.0214 (15)	−0.0065 (14)	−0.0006 (16)
O3	0.0370 (16)	0.0335 (14)	0.0501 (19)	−0.0112 (12)	0.0056 (13)	−0.0115 (13)
O4	0.0328 (15)	0.0575 (19)	0.0450 (18)	−0.0098 (14)	−0.0093 (13)	−0.0219 (15)
O5	0.0290 (14)	0.064 (2)	0.0425 (17)	−0.0157 (14)	−0.0025 (12)	−0.0207 (15)
O6	0.0366 (15)	0.0353 (14)	0.0426 (17)	−0.0136 (12)	−0.0019 (12)	−0.0130 (13)
O7	0.102 (5)	0.107 (4)	0.115 (5)	0.009 (4)	−0.034 (4)	−0.044 (4)
N1	0.0342 (17)	0.0396 (18)	0.0309 (17)	−0.0092 (14)	−0.0038 (13)	−0.0098 (14)
N2	0.0277 (16)	0.0416 (18)	0.0377 (19)	−0.0089 (14)	−0.0038 (13)	−0.0101 (15)
C1	0.039 (2)	0.055 (3)	0.041 (2)	−0.013 (2)	−0.0073 (18)	−0.015 (2)
C2	0.054 (3)	0.074 (3)	0.045 (3)	−0.025 (3)	−0.012 (2)	−0.021 (3)
C3	0.057 (3)	0.066 (3)	0.044 (3)	−0.025 (3)	0.001 (2)	−0.029 (2)
C4	0.048 (2)	0.045 (2)	0.040 (2)	−0.018 (2)	0.0058 (18)	−0.0173 (19)
C5	0.057 (3)	0.050 (3)	0.055 (3)	−0.015 (2)	0.010 (2)	−0.028 (2)
C6	0.045 (3)	0.046 (3)	0.054 (3)	−0.005 (2)	0.006 (2)	−0.016 (2)
C7	0.032 (2)	0.040 (2)	0.039 (2)	−0.0060 (17)	0.0039 (16)	−0.0048 (18)
C8	0.031 (2)	0.056 (3)	0.050 (3)	0.001 (2)	−0.0021 (19)	−0.011 (2)
C9	0.031 (2)	0.072 (3)	0.051 (3)	−0.008 (2)	−0.010 (2)	−0.013 (3)
C10	0.034 (2)	0.058 (3)	0.047 (3)	−0.014 (2)	−0.0086 (18)	−0.015 (2)
C11	0.0309 (19)	0.036 (2)	0.0279 (19)	−0.0103 (16)	0.0036 (15)	−0.0032 (15)
C12	0.0330 (19)	0.036 (2)	0.032 (2)	−0.0146 (16)	0.0026 (15)	−0.0083 (16)
C21	0.042 (2)	0.042 (2)	0.035 (2)	−0.0184 (19)	−0.0009 (17)	−0.0094 (18)
C22	0.066 (3)	0.060 (3)	0.041 (3)	−0.039 (3)	−0.001 (2)	−0.005 (2)
C23	0.081 (5)	0.117 (7)	0.073 (5)	−0.060 (5)	0.011 (4)	0.011 (4)
C24	0.114 (6)	0.088 (5)	0.070 (5)	−0.062 (5)	−0.030 (4)	0.028 (4)
C31	0.036 (2)	0.0344 (19)	0.034 (2)	−0.0127 (16)	−0.0078 (16)	−0.0089 (16)
C32	0.050 (3)	0.043 (2)	0.038 (2)	−0.025 (2)	0.0001 (18)	−0.0090 (19)
C33	0.078 (4)	0.045 (3)	0.078 (4)	−0.031 (3)	−0.002 (3)	−0.004 (3)
C34	0.051 (3)	0.062 (3)	0.090 (5)	−0.034 (3)	0.017 (3)	−0.026 (3)
C41	0.032 (2)	0.040 (2)	0.037 (2)	−0.0128 (17)	−0.0099 (16)	−0.0082 (17)
C42	0.037 (2)	0.058 (3)	0.049 (3)	−0.019 (2)	−0.0107 (19)	−0.018 (2)
C43	0.036 (3)	0.106 (5)	0.077 (4)	−0.025 (3)	−0.006 (2)	−0.048 (4)
C44	0.059 (4)	0.119 (6)	0.114 (6)	−0.030 (4)	−0.011 (4)	−0.077 (5)

Geometric parameters (Å, º)

La1—O1	2.584 (3)	C6—H6	0.9300
La1—O2	2.532 (3)	C7—C8	1.411 (7)
La1—O3	2.592 (3)	C7—C11	1.417 (6)
La1—O4	2.493 (3)	C8—C9	1.344 (8)
La1—O5	2.495 (3)	C8—H8	0.9300
La1—O6	2.457 (3)	C9—C10	1.398 (7)
La1—O6^i	2.718 (3)	C9—H9	0.9300
La1—N1	2.699 (4)	C10—H10	0.9300
La1—N2	2.719 (3)	C11—C12	1.450 (6)
La1—C21	2.932 (5)	C21—C22	1.493 (7)
La1—C31	3.025 (4)	C22—C23	1.389 (9)
La1—La1^i	4.0812 (5)	C22—C24	1.425 (9)
O1—C21	1.267 (5)	C23—H23A	0.9300
O2—C21	1.262 (6)	C23—H23B	0.9300
O3—C31	1.247 (5)	C24—H24A	0.9600
O4—C41	1.253 (5)	C24—H24B	0.9600
O5—C41^i	1.263 (5)	C24—H24C	0.9600
O6—C31^i	1.275 (5)	C31—O6^i	1.275 (5)
O6—La1^i	2.718 (3)	C31—C32	1.491 (6)
O7—HW1	0.9889	C32—C34	1.355 (8)
O7—HW2	0.9436	C32—C33	1.484 (7)
N1—C1	1.317 (6)	C33—H33A	0.9600
N1—C12	1.353 (5)	C33—H33B	0.9600
N2—C10	1.333 (6)	C33—H33C	0.9600
N2—C11	1.346 (6)	C34—H34A	0.9300
C1—C2	1.392 (7)	C34—H34B	0.9300
C1—H1	0.9300	C41—O5^i	1.263 (5)
C2—C3	1.367 (8)	C41—C42	1.508 (6)
C2—H2	0.9300	C42—C43	1.314 (7)
C3—C4	1.396 (7)	C42—C44	1.491 (8)
C3—H3	0.9300	C43—H43A	0.9300
C4—C12	1.409 (6)	C43—H43B	0.9300
C4—C5	1.450 (7)	C44—H44A	0.9600
C5—C6	1.344 (8)	C44—H44B	0.9600
C5—H5	0.9300	C44—H44C	0.9600
C6—C7	1.410 (8)
O1—La1—O2	50.95 (10)	C3—C2—C1	118.6 (5)
O1—La1—O3	142.83 (11)	C3—C2—H2	120.7
O1—La1—O4	130.93 (12)	C1—C2—H2	120.7
O1—La1—O5	73.18 (11)	C2—C3—C4	119.5 (5)
O1—La1—O6	78.78 (11)	C2—C3—H3	120.3
O1—La1—O6^i	135.08 (10)	C4—C3—H3	120.3
O1—La1—N1	74.92 (11)	C3—C4—C12	118.0 (5)
O1—La1—N2	108.10 (11)	C3—C4—C5	122.9 (5)
O2—La1—O3	140.11 (11)	C12—C4—C5	119.1 (5)
O2—La1—O4	91.21 (12)	C6—C5—C4	120.6 (5)
O2—La1—O5	123.99 (11)	C6—C5—H5	119.7
O2—La1—O6	91.88 (12)	C4—C5—H5	119.7
O2—La1—O6^i	163.02 (12)	C5—C6—C7	121.4 (5)
O2—La1—N1	82.83 (12)	C5—C6—H6	119.3
O2—La1—N2	69.10 (11)	C7—C6—H6	119.3
O3—La1—O4	86.02 (11)	C6—C7—C8	123.2 (4)
O3—La1—O5	82.51 (11)	C6—C7—C11	120.6 (5)
O3—La1—O6	124.43 (10)	C8—C7—C11	116.2 (5)
O3—La1—O6^i	48.72 (9)	C9—C8—C7	120.4 (4)
O3—La1—N1	73.11 (11)	C9—C8—H8	119.8
O3—La1—N2	71.41 (10)	C7—C8—H8	119.8
O4—La1—O5	135.27 (11)	C8—C9—C10	119.4 (5)
O4—La1—O6	71.82 (10)	C8—C9—H9	120.3
O4—La1—O6^i	73.86 (10)	C10—C9—H9	120.3
O4—La1—N1	137.58 (10)	N2—C10—C9	122.7 (5)
O4—La1—N2	78.01 (11)	N2—C10—H10	118.7
O5—La1—O6	79.63 (10)	C9—C10—H10	118.7
O5—La1—O6^i	66.15 (10)	N2—C11—C7	123.1 (4)
O5—La1—N1	79.00 (11)	N2—C11—C12	118.6 (4)
O5—La1—N2	136.47 (11)	C7—C11—C12	118.3 (4)
O6—La1—O6^i	76.00 (11)	N1—C12—C4	122.0 (4)
O6—La1—N1	149.92 (10)	N1—C12—C11	118.1 (4)
O6—La1—N2	143.90 (11)	C4—C12—C11	119.7 (4)
N1—La1—O6^i	113.60 (10)	O2—C21—O1	121.0 (4)
N1—La1—N2	60.58 (11)	O2—C21—C22	119.1 (4)
O6^i—La1—N2	114.23 (10)	O1—C21—C22	119.9 (4)
O6—La1—C21	84.63 (12)	O2—C21—La1	59.3 (2)
O4—La1—C21	111.75 (12)	O1—C21—La1	61.7 (2)
O5—La1—C21	98.71 (12)	C22—C21—La1	178.4 (3)
O2—La1—C21	25.37 (12)	C23—C22—C24	124.0 (6)
O1—La1—C21	25.58 (11)	C23—C22—C21	118.4 (5)
O3—La1—C21	150.28 (12)	C24—C22—C21	117.6 (5)
N1—La1—C21	77.97 (12)	C22—C23—H23A	120.0
O6^i—La1—C21	157.10 (11)	C22—C23—H23B	120.0
N2—La1—C21	88.62 (12)	H23A—C23—H23B	120.0
O6—La1—C31	100.92 (11)	C22—C24—H24A	109.5
O4—La1—C31	81.84 (11)	C22—C24—H24B	109.5
O5—La1—C31	70.44 (11)	H24A—C24—H24B	109.5
O2—La1—C31	162.64 (11)	C22—C24—H24C	109.5
O1—La1—C31	142.99 (11)	H24A—C24—H24C	109.5
O3—La1—C31	24.10 (10)	H24B—C24—H24C	109.5
N1—La1—C31	91.58 (11)	O3—C31—O6^i	120.9 (4)
O6^i—La1—C31	24.92 (10)	O3—C31—C32	119.7 (4)
N2—La1—C31	93.83 (11)	O6^i—C31—C32	119.4 (4)
C21—La1—C31	166.40 (12)	O3—C31—La1	58.1 (2)
O6—La1—La1^i	40.26 (7)	O6^i—C31—La1	64.0 (2)
O4—La1—La1^i	68.11 (7)	C32—C31—La1	166.3 (3)
O5—La1—La1^i	67.81 (8)	C34—C32—C33	124.1 (5)
O2—La1—La1^i	131.05 (9)	C34—C32—C31	118.8 (4)
O1—La1—La1^i	110.77 (8)	C33—C32—C31	117.1 (4)
O3—La1—La1^i	84.31 (7)	C32—C33—H33A	109.5
N1—La1—La1^i	141.96 (8)	C32—C33—H33B	109.5
O6^i—La1—La1^i	35.74 (6)	H33A—C33—H33B	109.5
N2—La1—La1^i	139.44 (8)	C32—C33—H33C	109.5
C21—La1—La1^i	123.87 (9)	H33A—C33—H33C	109.5
C31—La1—La1^i	60.66 (8)	H33B—C33—H33C	109.5
C21—O1—La1	92.8 (3)	C32—C34—H34A	120.0
C21—O2—La1	95.3 (3)	C32—C34—H34B	120.0
C31—O3—La1	97.8 (2)	H34A—C34—H34B	120.0
C41—O4—La1	134.4 (3)	O4—C41—O5^i	125.0 (4)
C41^i—O5—La1	137.8 (3)	O4—C41—C42	118.8 (4)
C31^i—O6—La1	164.9 (3)	O5^i—C41—C42	116.2 (4)
C31^i—O6—La1^i	91.1 (3)	C43—C42—C44	123.0 (5)
La1—O6—La1^i	104.00 (11)	C43—C42—C41	119.4 (5)
HW1—O7—HW2	104.2	C44—C42—C41	117.6 (4)
C1—N1—C12	118.0 (4)	C42—C43—H43A	120.0
C1—N1—La1	121.0 (3)	C42—C43—H43B	120.0
C12—N1—La1	120.4 (3)	H43A—C43—H43B	120.0
C10—N2—C11	118.0 (4)	C42—C44—H44A	109.5
C10—N2—La1	121.9 (3)	C42—C44—H44B	109.5
C11—N2—La1	120.0 (3)	H44A—C44—H44B	109.5
N1—C1—C2	124.0 (5)	C42—C44—H44C	109.5
N1—C1—H1	118.0	H44A—C44—H44C	109.5
C2—C1—H1	118.0	H44B—C44—H44C	109.5

Symmetry code: (i) −x+2, −y+1, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—HW1···O1	0.99	1.88	2.863 (5)	174