(1,10-Phenanthroline)tri(3-phenyl­propanoato)lanthanum(III)

Zhong, H.; Yang, X.-M.; Luo, Q.-Y.; Xu, Y.-P.

doi:10.1107/S1600536807028693

Retracted: (1,10-Phenanthroline)tri(3-phenylpropanoato)lanthanum(III)

H. Zhong, X.-M. Yang, Q.-Y. Luo and Y.-P. Xu

The La^III atom in the title complex, [La(C₉H₉O₂)₃(C₁₂H₈N₂)], is coordinated by two N atoms of a 1,10-phenanthroline (phen) ligand and four O atoms of three phenylpropanoate ligands. This mononuclear complex is further extended into a supramolecular network structure via nonclassical hydrogen bonds between CH groups of 1,10-phenanthroline or phenylpropanoate and O atoms of neighbouring phenylpropanoate ligands.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807028693/at2323sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807028693/at2323Isup2.hkl Contains datablock I

CCDC reference: 1249796

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.014 Å
R factor = 0.041
wR factor = 0.171
Data-to-parameter ratio = 19.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT241_ALERT_2_B Check High      Ueq as Compared to Neighbors for         C6
PLAT410_ALERT_2_B Short Intra H...H Contact  H12    ..  H24A    ..       1.88 Ang.

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.76 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C27
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C33
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        La1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C16
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C25
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C32
PLAT333_ALERT_2_C Large Average Benzene C-C Dist.  C4     -C6            1.44 Ang.
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         14
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C14    -   C15    ...       1.40 Ang.
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C32    -   C33    ...       1.38 Ang.
PLAT362_ALERT_2_C Short  C(sp3)-C(sp2) Bond  C15    -   C16    ...       1.37 Ang.
PLAT362_ALERT_2_C Short  C(sp3)-C(sp2) Bond  C24    -   C25    ...       1.37 Ang.
PLAT362_ALERT_2_C Short  C(sp3)-C(sp2) Bond  C33    -   C34    ...       1.32 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact  H14B   ..  H24B    ..       1.91 Ang.
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      78.00 A   3 

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for La1         (3)       3.15
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

   0 ALERT level A = In general: serious problem
   2 ALERT level B = Potentially serious problem
  16 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
  17 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

In recent years, there has been great interest in the synthesis of metal organic frameworks (MOFs) with organic ligands and rare earth metals because of their novel structures, fascinating properties and important roles in special materials having optical, electronic, magnetic and biological importance potential applications (Deborah et al., 2000; Farrugia et al., 2000; Tsukube & Shinoda, 2002; Zhang et al., 2005). These compounds are usually prepared by the reaction of rare-earth metal ions with bi- or multidentate ligands (Starynowicz, 1991, 1993; Kay et al., 1972; Ma et al., 1999; Zeng et al., 2000; 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). The six-coordinate environment of the La atom is completed by The two N atoms of 1,10-phenanthroline ligand and four O atoms of three benzenepropanoic acid ligands (Table 1). The La—O bond lengths are in the range 2.478 (4) to 2.908 (6) Å. The La—N bond lengths are in the range 2.717 (6) to 2.749 (5) Å. C—H···O non-classical hydrogen bonds between C—H groups of 1,10-phenanthroline or benzenepropanoic acid and O atoms of neighbouring benzenepropanoic acid molecules, with an average C···O distances of 3.235 (10) Å, generate a layered hydrogen-bonded network (Fig. 2 and Table 2). The non-classical hydrogen-bonding interactions link the mononuclear complex into a supramolecular network structure.

Related literature top

For related literature, see: Allen et al. (1987); Deborah et al. (2000); Farrugia et al. (2000); Kay et al. (1972); Ma et al. (1999); Mao et al. (1998); Starynowicz (1991, 1993); Tsukube & Shinoda (2002); Zhang et al. (2005); Zeng et al. (2000).

Experimental top

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Lanthanum (III) chloride hexahydrate (106.1 mg, 0.3 mmol), phen (59.4 mg, 0.3 mmol), benzenepropanoic acid (90.1 mg, 0.6 mmol) and distilled water (3.5 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 423 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colourless solution was decanted from small colourless 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. View of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonding interactions are shown as dashed lines.

(1,10-Phenanthroline)tri(3-phenylpropanoato)lanthanum(III) top

Crystal data top

[La(C₉H₉O₂)₃(C₁₂H₈N₂)]	F(000) = 1552
M_r = 766.60	D_x = 1.443 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9043 reflections
a = 19.904 (3) Å	θ = 2.5–26.9°
b = 8.783 (5) Å	µ = 1.26 mm⁻¹
c = 21.012 (2) Å	T = 273 K
β = 106.163 (2)°	Plane, colourless
V = 3528 (2) Å³	0.33 × 0.12 × 0.08 mm
Z = 4

Data collection top

Bruker APE XII area-detector diffractometer	7231 independent reflections
Radiation source: fine-focus sealed tube	4916 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
φ and ω scans	θ_max = 26.6°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −25→24
T_min = 0.682, T_max = 0.907	k = −10→11
26367 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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.171	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.1521P)² + 0.285P] where P = (F_o² + 2F_c²)/3
7231 reflections	(Δ/σ)_max = 0.003
373 parameters	Δρ_max = 1.05 e Å⁻³
4 restraints	Δρ_min = −1.18 e Å⁻³

Crystal data top

[La(C₉H₉O₂)₃(C₁₂H₈N₂)]	V = 3528 (2) Å³
M_r = 766.60	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 19.904 (3) Å	µ = 1.26 mm⁻¹
b = 8.783 (5) Å	T = 273 K
c = 21.012 (2) Å	0.33 × 0.12 × 0.08 mm
β = 106.163 (2)°

Data collection top

Bruker APE XII area-detector diffractometer	7231 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4916 reflections with I > 2σ(I)
T_min = 0.682, T_max = 0.907	R_int = 0.042
26367 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	4 restraints
wR(F²) = 0.171	H-atom parameters constrained
S = 0.96	Δρ_max = 1.05 e Å⁻³
7231 reflections	Δρ_min = −1.18 e Å⁻³
373 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	0.931195 (16)	0.19073 (4)	0.964267 (15)	0.04126 (16)
O1	0.9710 (2)	0.0605 (5)	0.8751 (2)	0.0567 (11)
O2	1.0666 (2)	−0.0830 (6)	0.9217 (2)	0.0606 (12)
O4	0.9402 (2)	0.4212 (5)	1.0342 (2)	0.0565 (11)
O5	1.0078 (3)	0.6126 (6)	1.0912 (2)	0.0669 (13)
O7	0.8464 (2)	−0.0365 (5)	0.9192 (2)	0.0536 (10)
O8	0.9469 (2)	−0.1380 (6)	0.9773 (2)	0.0588 (11)
N1	0.7968 (3)	0.2345 (7)	0.9665 (3)	0.0577 (13)
N2	0.8346 (3)	0.3067 (6)	0.8549 (3)	0.0562 (14)
C1	0.7780 (4)	0.1909 (9)	1.0205 (4)	0.073 (2)
H1	0.8126	0.1683	1.0592	0.088*
C2	0.7095 (5)	0.1790 (11)	1.0201 (5)	0.096 (3)
H2	0.6974	0.1487	1.0578	0.115*
C3	0.6579 (5)	0.2135 (12)	0.9613 (6)	0.103 (4)
H3	0.6111	0.2053	0.9605	0.123*
C4	0.6744 (4)	0.2596 (13)	0.9041 (5)	0.088 (3)
C5	0.7461 (4)	0.2671 (8)	0.9093 (4)	0.0613 (17)
C6	0.6192 (6)	0.2951 (16)	0.8423 (7)	0.137 (6)
H6	0.5720	0.2859	0.8398	0.165*
C7	0.6419 (5)	0.3449 (14)	0.7854 (5)	0.111 (4)
H7	0.6091	0.3711	0.7459	0.133*
C8	0.7127 (5)	0.3529 (11)	0.7907 (4)	0.083 (3)
C9	0.7658 (4)	0.3097 (7)	0.8501 (4)	0.0601 (19)
C10	0.7367 (6)	0.4012 (12)	0.7367 (4)	0.096 (3)
H10	0.7048	0.4318	0.6975	0.116*
C11	0.8049 (6)	0.4030 (11)	0.7419 (4)	0.092 (3)
H11	0.8210	0.4403	0.7074	0.110*
C12	0.8525 (5)	0.3479 (9)	0.8001 (4)	0.072 (2)
H12	0.8993	0.3395	0.8007	0.086*
C13	1.0282 (3)	0.0026 (7)	0.8772 (3)	0.0506 (14)
C14	1.0520 (3)	0.0495 (8)	0.8169 (3)	0.0573 (9)
H14A	1.0179	0.0163	0.7767	0.069*
H14B	1.0557	0.1595	0.8155	0.069*
C15	1.1171 (3)	−0.0166 (8)	0.8208 (3)	0.0573 (9)
H15A	1.1499	0.0168	0.8617	0.069*
H15B	1.1124	−0.1261	0.8236	0.069*
C16	1.1455 (3)	0.0142 (8)	0.7698 (3)	0.0573 (9)
C17	1.2069 (5)	−0.0559 (12)	0.7763 (5)	0.095 (3)
H17	1.2272	−0.1153	0.8133	0.113*
C18	1.2400 (5)	−0.0370 (14)	0.7251 (6)	0.108 (3)
H18	1.2821	−0.0858	0.7276	0.129*
C19	1.2087 (7)	0.0555 (13)	0.6709 (7)	0.119 (4)
H19	1.2310	0.0683	0.6377	0.142*
C20	1.1488 (7)	0.1251 (15)	0.6652 (6)	0.122 (4)
H20	1.1288	0.1844	0.6281	0.146*
C21	1.1144 (5)	0.1094 (12)	0.7162 (5)	0.096 (3)
H21	1.0729	0.1607	0.7139	0.115*
C22	0.9691 (3)	0.4986 (7)	1.0859 (3)	0.0522 (15)
C23	0.9485 (4)	0.4458 (8)	1.1470 (3)	0.0543 (9)
H23B	0.8987	0.4610	1.1397	0.065*
H23A	0.9580	0.3377	1.1535	0.065*
C24	0.9861 (4)	0.5271 (8)	1.2062 (3)	0.0543 (9)
H24A	1.0357	0.5149	1.2110	0.065*
H24B	0.9755	0.6345	1.1986	0.065*
C25	0.9745 (4)	0.4892 (7)	1.2653 (3)	0.0543 (9)
C26	0.9276 (4)	0.3793 (12)	1.2714 (4)	0.084 (2)
H26	0.9016	0.3257	1.2346	0.101*
C27	0.9198 (7)	0.3499 (16)	1.3343 (5)	0.126 (5)
H27	0.8900	0.2724	1.3397	0.151*
C28	0.9559 (6)	0.4345 (15)	1.3892 (5)	0.115 (4)
H28	0.9470	0.4187	1.4299	0.137*
C29	1.0048 (5)	0.5416 (13)	1.3838 (4)	0.102 (3)
H29	1.0305	0.5945	1.4210	0.122*
C30	1.0153 (4)	0.5697 (10)	1.3218 (4)	0.082 (2)
H30	1.0485	0.6403	1.3174	0.099*
C31	0.8838 (3)	−0.1527 (8)	0.9391 (3)	0.0517 (15)
C32	0.8576 (4)	−0.3131 (8)	0.9188 (4)	0.0626 (19)
H32A	0.8759	−0.3452	0.8827	0.075*
H32B	0.8769	−0.3808	0.9559	0.075*
C33	0.7861 (6)	−0.3313 (11)	0.8993 (6)	0.1096 (14)
H33A	0.7668	−0.2589	0.8641	0.132*
H33B	0.7760	−0.4324	0.8806	0.132*
C34	0.7529 (7)	−0.3143 (9)	0.9451 (7)	0.1096 (14)
C35	0.7848 (7)	−0.2738 (12)	1.0127 (7)	0.1096 (14)
H35	0.8325	−0.2547	1.0288	0.132*
C36	0.7374 (6)	−0.2645 (13)	1.0548 (7)	0.1096 (14)
H36	0.7530	−0.2390	1.0995	0.132*
C37	0.6703 (7)	−0.2950 (11)	1.0249 (7)	0.1096 (14)
H37	0.6403	−0.2876	1.0517	0.132*
C38	0.6407 (7)	−0.3338 (12)	0.9634 (7)	0.1096 (14)
H38	0.5934	−0.3584	0.9491	0.132*
C39	0.6811 (6)	−0.3370 (12)	0.9211 (7)	0.1096 (14)
H39	0.6609	−0.3544	0.8762	0.132*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
La1	0.0460 (2)	0.0376 (2)	0.0358 (2)	−0.00143 (13)	0.00419 (15)	0.00054 (13)
O1	0.064 (3)	0.057 (3)	0.052 (2)	0.005 (2)	0.019 (2)	0.003 (2)
O2	0.068 (3)	0.066 (3)	0.050 (3)	0.008 (2)	0.019 (2)	0.014 (2)
O4	0.074 (3)	0.047 (3)	0.047 (2)	−0.003 (2)	0.014 (2)	−0.008 (2)
O5	0.091 (4)	0.067 (3)	0.045 (3)	−0.029 (3)	0.021 (2)	0.000 (2)
O7	0.049 (2)	0.047 (3)	0.057 (3)	−0.003 (2)	0.0016 (19)	−0.003 (2)
O8	0.056 (3)	0.061 (3)	0.053 (3)	−0.003 (2)	0.002 (2)	0.007 (2)
N1	0.054 (3)	0.056 (3)	0.058 (3)	0.005 (3)	0.006 (3)	−0.005 (3)
N2	0.066 (4)	0.054 (4)	0.042 (3)	0.004 (3)	0.003 (3)	0.002 (2)
C1	0.064 (5)	0.094 (7)	0.062 (5)	0.009 (4)	0.017 (4)	−0.002 (4)
C2	0.057 (5)	0.147 (10)	0.087 (7)	−0.003 (5)	0.025 (5)	−0.016 (6)
C3	0.054 (5)	0.123 (10)	0.129 (10)	−0.005 (5)	0.023 (6)	−0.013 (7)
C4	0.057 (5)	0.105 (7)	0.088 (7)	0.007 (5)	−0.005 (4)	−0.022 (6)
C5	0.062 (4)	0.042 (4)	0.073 (5)	0.007 (3)	0.007 (3)	−0.007 (3)
C6	0.055 (6)	0.207 (17)	0.137 (12)	−0.001 (7)	0.004 (6)	−0.023 (10)
C7	0.074 (6)	0.153 (10)	0.079 (6)	0.043 (6)	−0.022 (5)	0.007 (6)
C8	0.082 (6)	0.081 (5)	0.062 (5)	0.020 (5)	−0.018 (4)	−0.010 (4)
C9	0.067 (4)	0.049 (4)	0.050 (4)	0.001 (3)	−0.009 (3)	−0.007 (3)
C10	0.119 (8)	0.091 (7)	0.055 (5)	0.016 (6)	−0.015 (5)	−0.002 (4)
C11	0.130 (8)	0.090 (7)	0.043 (4)	0.001 (6)	0.003 (5)	0.014 (4)
C12	0.091 (6)	0.060 (5)	0.055 (4)	−0.003 (4)	0.006 (4)	0.009 (3)
C13	0.054 (4)	0.045 (4)	0.050 (4)	−0.005 (3)	0.012 (3)	0.001 (3)
C14	0.061 (2)	0.063 (3)	0.053 (2)	0.0072 (19)	0.0242 (18)	0.0129 (18)
C15	0.061 (2)	0.063 (3)	0.053 (2)	0.0072 (19)	0.0242 (18)	0.0129 (18)
C16	0.061 (2)	0.063 (3)	0.053 (2)	0.0072 (19)	0.0242 (18)	0.0129 (18)
C17	0.093 (6)	0.121 (8)	0.083 (6)	0.008 (6)	0.047 (5)	−0.001 (5)
C18	0.093 (7)	0.125 (10)	0.121 (8)	−0.009 (6)	0.057 (6)	−0.007 (7)
C19	0.151 (10)	0.096 (8)	0.151 (10)	−0.015 (7)	0.111 (9)	−0.004 (7)
C20	0.165 (11)	0.123 (9)	0.107 (8)	0.021 (9)	0.087 (9)	0.038 (7)
C21	0.113 (7)	0.099 (7)	0.098 (7)	0.000 (6)	0.066 (6)	0.017 (6)
C22	0.064 (4)	0.039 (4)	0.053 (4)	−0.002 (3)	0.016 (3)	0.001 (3)
C23	0.074 (2)	0.052 (2)	0.0390 (18)	−0.0157 (18)	0.0188 (17)	−0.0037 (15)
C24	0.074 (2)	0.052 (2)	0.0390 (18)	−0.0157 (18)	0.0188 (17)	−0.0037 (15)
C25	0.074 (2)	0.052 (2)	0.0390 (18)	−0.0157 (18)	0.0188 (17)	−0.0037 (15)
C26	0.084 (5)	0.110 (7)	0.063 (5)	−0.039 (5)	0.026 (4)	−0.013 (5)
C27	0.157 (11)	0.167 (11)	0.066 (6)	−0.065 (9)	0.052 (7)	−0.010 (7)
C28	0.132 (9)	0.155 (11)	0.069 (6)	−0.014 (8)	0.049 (6)	0.016 (7)
C29	0.130 (8)	0.117 (8)	0.053 (5)	−0.017 (7)	0.018 (5)	−0.002 (5)
C30	0.092 (6)	0.092 (6)	0.060 (5)	−0.030 (5)	0.016 (4)	−0.014 (4)
C31	0.050 (3)	0.062 (4)	0.039 (3)	0.002 (3)	0.005 (3)	−0.001 (3)
C32	0.060 (4)	0.061 (5)	0.060 (4)	0.011 (3)	0.007 (3)	−0.006 (3)
C33	0.108 (3)	0.091 (3)	0.135 (4)	0.000 (2)	0.044 (3)	0.017 (3)
C34	0.108 (3)	0.091 (3)	0.135 (4)	0.000 (2)	0.044 (3)	0.017 (3)
C35	0.108 (3)	0.091 (3)	0.135 (4)	0.000 (2)	0.044 (3)	0.017 (3)
C36	0.108 (3)	0.091 (3)	0.135 (4)	0.000 (2)	0.044 (3)	0.017 (3)
C37	0.108 (3)	0.091 (3)	0.135 (4)	0.000 (2)	0.044 (3)	0.017 (3)
C38	0.108 (3)	0.091 (3)	0.135 (4)	0.000 (2)	0.044 (3)	0.017 (3)
C39	0.108 (3)	0.091 (3)	0.135 (4)	0.000 (2)	0.044 (3)	0.017 (3)

Geometric parameters (Å, º) top

La1—O1	2.504 (4)	C15—H15B	0.9700
La1—O4	2.478 (4)	C16—C17	1.341 (11)
La1—O7	2.615 (4)	C16—C21	1.401 (11)
La1—O8	2.908 (6)	C17—C18	1.419 (13)
La1—N1	2.717 (6)	C17—H17	0.9300
La1—N2	2.749 (5)	C18—C19	1.396 (16)
La1—O8ⁱ	2.440 (5)	C18—H18	0.9300
La1—O2ⁱ	2.566 (4)	C19—C20	1.317 (15)
La1—O5ⁱⁱ	2.570 (4)	C19—H19	0.9300
O1—C13	1.237 (7)	C20—C21	1.429 (12)
O2—C13	1.276 (7)	C20—H20	0.9300
O2—La1ⁱ	2.566 (4)	C21—H21	0.9300
O4—C22	1.275 (8)	C22—C23	1.524 (8)
O5—C22	1.250 (8)	C23—C24	1.448 (8)
O5—La1ⁱⁱ	2.570 (4)	C23—H23B	0.9700
O7—C31	1.263 (8)	C23—H23A	0.9700
O8—C31	1.295 (8)	C24—C25	1.366 (8)
O8—La1ⁱ	2.440 (5)	C24—H24A	0.9700
N1—C1	1.344 (10)	C24—H24B	0.9700
N1—C5	1.367 (9)	C25—C26	1.374 (10)
N2—C9	1.345 (10)	C25—C30	1.425 (9)
N2—C12	1.346 (9)	C26—C27	1.397 (12)
C1—C2	1.365 (11)	C26—H26	0.9300
C1—H1	0.9300	C27—C28	1.391 (15)
C2—C3	1.402 (15)	C27—H27	0.9300
C2—H2	0.9300	C28—C29	1.381 (14)
C3—C4	1.390 (14)	C28—H28	0.9300
C3—H3	0.9300	C29—C30	1.397 (11)
C4—C5	1.404 (11)	C29—H29	0.9300
C4—C6	1.483 (15)	C30—H30	0.9300
C5—C9	1.453 (11)	C31—C32	1.521 (10)
C6—C7	1.458 (16)	C32—C33	1.376 (13)
C6—H6	0.9300	C32—H32A	0.9700
C7—C8	1.385 (14)	C32—H32B	0.9700
C7—H7	0.9300	C33—C34	1.319 (16)
C8—C10	1.412 (13)	C33—H33A	0.9700
C8—C9	1.444 (10)	C33—H33B	0.9700
C10—C11	1.332 (12)	C34—C39	1.390 (16)
C10—H10	0.9300	C34—C35	1.430 (18)
C11—C12	1.407 (11)	C35—C36	1.467 (15)
C11—H11	0.9300	C35—H35	0.9300
C12—H12	0.9300	C36—C37	1.335 (15)
C13—C14	1.527 (8)	C36—H36	0.9300
C14—C15	1.400 (8)	C37—C38	1.309 (16)
C14—H14A	0.9700	C37—H37	0.9300
C14—H14B	0.9700	C38—C39	1.354 (15)
C15—C16	1.370 (8)	C38—H38	0.9300
C15—H15A	0.9700	C39—H39	0.9300

O1—La1—O4	146.17 (15)	C13—C14—H14B	109.7
O1—La1—O7	71.74 (14)	H14A—C14—H14B	108.2
O1—La1—O8	64.45 (14)	C16—C15—C14	116.7 (6)
O4—La1—O7	140.47 (15)	C16—C15—H15A	108.1
O4—La1—O8	140.10 (13)	C14—C15—H15A	108.1
O7—La1—O8	47.01 (13)	C16—C15—H15B	108.1
O1—La1—N1	126.56 (16)	C14—C15—H15B	108.1
O4—La1—N1	77.48 (16)	H15A—C15—H15B	107.3
O7—La1—N1	64.84 (16)	C17—C16—C15	113.1 (7)
O8—La1—N1	102.67 (16)	C17—C16—C21	122.8 (7)
O1—La1—N2	80.59 (16)	C15—C16—C21	124.1 (7)
O4—La1—N2	96.40 (15)	C16—C17—C18	118.1 (10)
O7—La1—N2	75.47 (15)	C16—C17—H17	121.0
O8—La1—N2	118.56 (14)	C18—C17—H17	121.0
N1—La1—N2	59.97 (18)	C19—C18—C17	119.4 (10)
O8ⁱ—La1—O4	87.64 (17)	C19—C18—H18	120.3
O8ⁱ—La1—O1	79.22 (15)	C17—C18—H18	120.3
O8ⁱ—La1—O2ⁱ	72.78 (15)	C20—C19—C18	122.0 (10)
O4—La1—O2ⁱ	76.59 (15)	C20—C19—H19	119.0
O1—La1—O2ⁱ	127.14 (16)	C18—C19—H19	119.0
O8ⁱ—La1—O5ⁱⁱ	80.04 (17)	C19—C20—C21	119.9 (11)
O4—La1—O5ⁱⁱ	75.77 (15)	C19—C20—H20	120.1
O1—La1—O5ⁱⁱ	71.35 (15)	C21—C20—H20	120.1
O2ⁱ—La1—O5ⁱⁱ	141.66 (15)	C16—C21—C20	117.6 (9)
O8ⁱ—La1—O7	119.25 (17)	C16—C21—H21	121.2
O2ⁱ—La1—O7	84.17 (15)	C20—C21—H21	121.2
O5ⁱⁱ—La1—O7	133.41 (14)	O5—C22—O4	128.5 (6)
O8ⁱ—La1—N1	149.81 (16)	O5—C22—C23	118.2 (6)
O2ⁱ—La1—N1	78.24 (16)	O4—C22—C23	113.2 (5)
O5ⁱⁱ—La1—N1	120.31 (18)	C24—C23—C22	112.2 (5)
O8ⁱ—La1—N2	149.02 (17)	C24—C23—H23B	109.2
O2ⁱ—La1—N2	138.05 (17)	C22—C23—H23B	109.2
O5ⁱⁱ—La1—N2	71.35 (17)	C24—C23—H23A	109.2
O8ⁱ—La1—O8	72.45 (18)	C22—C23—H23A	109.2
O2ⁱ—La1—O8	64.71 (14)	H23B—C23—H23A	107.9
O5ⁱⁱ—La1—O8	131.14 (15)	C25—C24—C23	118.9 (6)
C13—O1—La1	129.9 (4)	C25—C24—H24A	107.6
C13—O2—La1ⁱ	138.8 (4)	C23—C24—H24A	107.6
C22—O4—La1	151.8 (4)	C25—C24—H24B	107.6
C22—O5—La1ⁱⁱ	148.9 (4)	C23—C24—H24B	107.6
C31—O7—La1	103.6 (4)	H24A—C24—H24B	107.0
C31—O8—La1ⁱ	161.9 (5)	C24—C25—C26	123.2 (6)
C31—O8—La1	88.9 (4)	C24—C25—C30	115.9 (6)
La1ⁱ—O8—La1	107.55 (18)	C26—C25—C30	121.0 (6)
C1—N1—C5	119.5 (6)	C25—C26—C27	118.4 (8)
C1—N1—La1	118.8 (5)	C25—C26—H26	120.8
C5—N1—La1	120.1 (5)	C27—C26—H26	120.8
C9—N2—C12	115.9 (6)	C28—C27—C26	121.2 (10)
C9—N2—La1	122.0 (4)	C28—C27—H27	119.4
C12—N2—La1	121.7 (5)	C26—C27—H27	119.4
N1—C1—C2	121.9 (8)	C29—C28—C27	120.6 (9)
N1—C1—H1	119.0	C29—C28—H28	119.7
C2—C1—H1	119.0	C27—C28—H28	119.7
C1—C2—C3	118.3 (9)	C28—C29—C30	119.2 (9)
C1—C2—H2	120.9	C28—C29—H29	120.4
C3—C2—H2	120.9	C30—C29—H29	120.4
C4—C3—C2	122.2 (9)	C29—C30—C25	119.4 (8)
C4—C3—H3	118.9	C29—C30—H30	120.3
C2—C3—H3	118.9	C25—C30—H30	120.3
C3—C4—C5	115.3 (8)	O7—C31—O8	120.3 (6)
C3—C4—C6	121.5 (9)	O7—C31—C32	122.1 (6)
C5—C4—C6	123.2 (10)	O8—C31—C32	117.6 (6)
N1—C5—C4	122.9 (8)	C33—C32—C31	115.8 (7)
N1—C5—C9	119.9 (6)	C33—C32—H32A	108.3
C4—C5—C9	117.2 (7)	C31—C32—H32A	108.3
C7—C6—C4	117.3 (9)	C33—C32—H32B	108.3
C7—C6—H6	121.3	C31—C32—H32B	108.3
C4—C6—H6	121.3	H32A—C32—H32B	107.4
C8—C7—C6	119.4 (8)	C34—C33—C32	117.2 (12)
C8—C7—H7	120.3	C34—C33—H33A	108.0
C6—C7—H7	120.3	C32—C33—H33A	108.0
C7—C8—C10	121.0 (9)	C34—C33—H33B	108.0
C7—C8—C9	122.7 (9)	C32—C33—H33B	108.0
C10—C8—C9	116.3 (8)	H33A—C33—H33B	107.2
N2—C9—C8	123.7 (8)	C33—C34—C39	113.2 (14)
N2—C9—C5	116.3 (6)	C33—C34—C35	125.2 (13)
C8—C9—C5	120.1 (8)	C39—C34—C35	121.6 (12)
C11—C10—C8	120.2 (8)	C34—C35—C36	115.5 (12)
C11—C10—H10	119.9	C34—C35—H35	122.2
C8—C10—H10	119.9	C36—C35—H35	122.2
C10—C11—C12	119.4 (9)	C37—C36—C35	115.6 (13)
C10—C11—H11	120.3	C37—C36—H36	122.2
C12—C11—H11	120.3	C35—C36—H36	122.2
N2—C12—C11	124.2 (9)	C38—C37—C36	129.3 (13)
N2—C12—H12	117.9	C38—C37—H37	115.3
C11—C12—H12	117.9	C36—C37—H37	115.3
O1—C13—O2	128.8 (6)	C37—C38—C39	117.9 (13)
O1—C13—C14	110.8 (5)	C37—C38—H38	121.1
O2—C13—C14	120.3 (6)	C39—C38—H38	121.1
C15—C14—C13	109.6 (5)	C38—C39—C34	119.8 (14)
C15—C14—H14A	109.7	C38—C39—H39	120.1
C13—C14—H14A	109.7	C34—C39—H39	120.1
C15—C14—H14B	109.7

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
C1—H1···O2ⁱ	0.93	2.44	3.138 (10)	132
C12—H12···O5ⁱⁱ	0.93	2.53	3.087 (9)	119
C32—H32B···O4ⁱⁱⁱ	0.97	2.48	3.435 (9)	167
C10—H10···O7^iv	0.93	2.39	3.279 (9)	159

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

Experimental details

Crystal data
Chemical formula	[La(C₉H₉O₂)₃(C₁₂H₈N₂)]
M_r	766.60
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	273
a, b, c (Å)	19.904 (3), 8.783 (5), 21.012 (2)
β (°)	106.163 (2)
V (Å³)	3528 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.26
Crystal size (mm)	0.33 × 0.12 × 0.08

Data collection
Diffractometer	Bruker APE XII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.682, 0.907
No. of measured, independent and observed [I > 2σ(I)] reflections	26367, 7231, 4916
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.629

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.171, 0.96
No. of reflections	7231
No. of parameters	373
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.05, −1.18

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