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In the crystal structure of the title compound, [La2(C8H8NO2)6(C12H8N2)2]n, the LaIII atoms are bridged by two tridentate, two bidentate and four mondentate carboxylate groups with an inversion centre between the two LaIII ions. Each La atom is nine-coordinated by two 1,10-phenanthroline N atoms and seven O atoms of four anilinoacetate ligands. In the crystal structure, the chains are linked by hydrogen bonds into a polymeric sheet structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807051240/at2426sup1.cif
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807051240/at2426Isup2.hkl
Contains datablock I

CCDC reference: 1168215

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.038
  • wR factor = 0.100
  • Data-to-parameter ratio = 16.0

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for N5
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.50 PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.79 Ratio 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 C23 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C33 PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C15 -C20 1.36 Ang. PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C31 -C36 1.37 Ang. PLAT335_ALERT_2_C Large Benzene C-C Range ....... C4 -C6 0.19 Ang. PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10 PLAT420_ALERT_2_C D-H Without Acceptor N3 - H3A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N4 - H4A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N5 - H5A ... ? PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 72.00 A   3
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for La1 (3) 3.47 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 5
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 17 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 13 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 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check

Comment top

The crystal structure of catena-Poly[bis(µ-anilinoacetato-κ2O:O')bis (µ-anilinoacetato-κ3O,O':O)bis[(1,10-phenanthroline-κ2N,N') samarium(III)]-µ-anilinoacetato-κ2O:O'], (II), and catena- Poly[[tetra-µ-anilinoacetato-bis(1,10-phenanthroline) dineodymium(III)]-di-µ-anilinoacetato], (III), have previously been reported (Zhong et al., 2007a,b). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II) and (III). We report herein the crystal structure of (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The title compound, [La2(C8H8NO2)6(C12H8N2)2]n, which are bridged by two terdentate, two bidentate and four mondentate carboxyl groups with an inversion centre between the two LaIII ions. Each La atom is nine-coordinated by two N atoms of 1,10-phenanthroline (phen) ligand and seven O atoms of four anilinoacetate ligands (Table 1). The La—O bond lengths are in the range 2.399 (3) to 2.815 (3) Å. The La—N bond lengths are in the range 2.703 (3) to 2.756 (4) Å, as in (II) and (III).

In the crystal structure, C—H···N and C—H···O hydrogen bonds (Fig. 2 and Table 2) seem to be effective in the stabilization of the structure, resulting in the formation of a supramolecular network structure, as in (II) and (III).

The three compounds, (I), (II) and (III), are isostructural.

Related literature top

For related structures, see: Zhong et al. (2007a,b). For bond-length data, see: Allen et al. (1987).

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) nitrate hexahydrate (213.2 mg, 0.5 mmol), phen (198 mg, 1 mmol), anilinoacetic acid (292.4 mg, 2 mmol), ammonia (0.5 mol/l, 4 ml) and distilled water (10 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 453 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.

Refinement top

H3A and H4A (for NH) were located in difference syntheses and refined isotropically [N—H = 0.771 (18) and 0.80 (4) Å, Uiso(H) = 0.072 (13) and 0.077 (16) Å2]. The other H atoms were positioned geometrically, with N—H = 0.86 Å (for NH) and C—H = 0.93 - 0.97 Å (for CH), and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.2 for aromatic H atoms and x = 1.5 for all other H atoms.

Structure description top

The crystal structure of catena-Poly[bis(µ-anilinoacetato-κ2O:O')bis (µ-anilinoacetato-κ3O,O':O)bis[(1,10-phenanthroline-κ2N,N') samarium(III)]-µ-anilinoacetato-κ2O:O'], (II), and catena- Poly[[tetra-µ-anilinoacetato-bis(1,10-phenanthroline) dineodymium(III)]-di-µ-anilinoacetato], (III), have previously been reported (Zhong et al., 2007a,b). The crystal structure determination of the title compound, (I), has been carried out in order to elucidate the molecular conformation and to compare it with that of (II) and (III). We report herein the crystal structure of (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). The title compound, [La2(C8H8NO2)6(C12H8N2)2]n, which are bridged by two terdentate, two bidentate and four mondentate carboxyl groups with an inversion centre between the two LaIII ions. Each La atom is nine-coordinated by two N atoms of 1,10-phenanthroline (phen) ligand and seven O atoms of four anilinoacetate ligands (Table 1). The La—O bond lengths are in the range 2.399 (3) to 2.815 (3) Å. The La—N bond lengths are in the range 2.703 (3) to 2.756 (4) Å, as in (II) and (III).

In the crystal structure, C—H···N and C—H···O hydrogen bonds (Fig. 2 and Table 2) seem to be effective in the stabilization of the structure, resulting in the formation of a supramolecular network structure, as in (II) and (III).

The three compounds, (I), (II) and (III), are isostructural.

For related structures, see: Zhong et al. (2007a,b). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: APEX2 (Bruker, 2005); 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
[Figure 1] Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. [Ssymmetry code (A): 2 - x, -y, 2 - z]. All H atoms have been omitted for clarity.
[Figure 2] Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.
catena-Poly[[tetra-µ-anilinoacetato-bis(1,10-phenanthroline) dilanthanum(III)]-di-µ-anilinoacetato] top
Crystal data top
[La2(C8H8NO2)6(C12H8N2)2]F(000) = 1552
Mr = 1539.16Dx = 1.519 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9108 reflections
a = 20.2217 (15) Åθ = 2.3–26.5°
b = 8.5007 (18) ŵ = 1.32 mm1
c = 20.449 (3) ÅT = 273 K
β = 106.801 (3)°Plane, colourless
V = 3365.1 (9) Å30.32 × 0.13 × 0.08 mm
Z = 2
Data collection top
Bruker APEX-II area-detector
diffractometer
6591 independent reflections
Radiation source: fine-focus sealed tube4615 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.040
φ and ω scansθmax = 26.2°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 2524
Tmin = 0.674, Tmax = 0.900k = 1010
24428 measured reflectionsl = 2525
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 0.96 w = 1/[σ2(Fo2) + (0.058P)2 + 1.1179P]
where P = (Fo2 + 2Fc2)/3
6591 reflections(Δ/σ)max = 0.004
411 parametersΔρmax = 1.36 e Å3
5 restraintsΔρmin = 0.54 e Å3
Crystal data top
[La2(C8H8NO2)6(C12H8N2)2]V = 3365.1 (9) Å3
Mr = 1539.16Z = 2
Monoclinic, P21/nMo Kα radiation
a = 20.2217 (15) ŵ = 1.32 mm1
b = 8.5007 (18) ÅT = 273 K
c = 20.449 (3) Å0.32 × 0.13 × 0.08 mm
β = 106.801 (3)°
Data collection top
Bruker APEX-II area-detector
diffractometer
6591 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4615 reflections with I > 2σ(I)
Tmin = 0.674, Tmax = 0.900Rint = 0.040
24428 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0385 restraints
wR(F2) = 0.100H atoms treated by a mixture of independent and constrained refinement
S = 0.96Δρmax = 1.36 e Å3
6591 reflectionsΔρmin = 0.54 e Å3
411 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
xyzUiso*/Ueq
La10.931209 (11)0.19062 (3)0.964286 (10)0.03914 (9)
O10.84636 (14)0.0359 (3)0.91878 (14)0.0506 (7)
O20.94664 (14)0.1380 (4)0.97703 (14)0.0556 (7)
O30.97057 (15)0.0601 (3)0.87468 (13)0.0531 (7)
O40.93991 (15)0.4210 (3)1.03409 (13)0.0535 (7)
O51.06690 (15)0.0828 (4)0.92160 (14)0.0557 (7)
O61.00768 (17)0.6126 (4)1.09102 (14)0.0634 (8)
N10.79693 (18)0.2346 (4)0.96678 (19)0.0533 (9)
N20.8342 (2)0.3065 (4)0.85460 (17)0.0531 (9)
N31.1193 (2)0.0138 (5)0.82285 (19)0.0536 (9)
N50.78527 (18)0.3273 (4)0.89864 (19)0.0511 (9)
H5A0.76290.34360.85650.061*
N40.9879 (2)0.5258 (5)1.20644 (16)0.0494 (9)
C10.7784 (3)0.1913 (6)1.0202 (3)0.0688 (13)
H10.81270.16721.06020.083*
C20.7093 (3)0.1794 (7)1.0201 (3)0.0902 (19)
H20.69850.15021.05970.108*
C30.6579 (3)0.2110 (8)0.9617 (4)0.098 (2)
H30.61190.19950.96060.118*
C40.6745 (3)0.2594 (8)0.9051 (3)0.0825 (17)
C50.7461 (2)0.2673 (5)0.9089 (2)0.0577 (12)
C60.6230 (3)0.2966 (9)0.8392 (4)0.114 (3)
H60.57620.28530.83510.137*
C70.6417 (4)0.3442 (9)0.7875 (4)0.105 (2)
H70.60830.37290.74750.126*
C80.7136 (3)0.3536 (7)0.7910 (3)0.0761 (16)
C90.7658 (2)0.3102 (5)0.8506 (2)0.0577 (12)
C100.7356 (4)0.4037 (7)0.7369 (3)0.093 (2)
H100.70350.43970.69740.112*
C110.8041 (4)0.4012 (7)0.7406 (3)0.0897 (19)
H110.81860.43360.70350.108*
C120.8526 (3)0.3493 (6)0.8008 (2)0.0703 (14)
H120.89900.34510.80250.084*
C131.0289 (2)0.0032 (5)0.8771 (2)0.0476 (10)
C141.0525 (2)0.0504 (6)0.8173 (2)0.0598 (12)
H14A1.01980.01330.77560.072*
H14B1.05450.16420.81510.072*
C151.1460 (3)0.0147 (6)0.7701 (3)0.0692 (13)
C161.2079 (3)0.0558 (8)0.7765 (3)0.0866 (17)
H161.22840.11730.81450.104*
C171.2398 (4)0.0358 (9)0.7268 (4)0.102 (2)
H171.28210.08400.73060.122*
C181.2097 (5)0.0543 (9)0.6720 (4)0.112 (2)
H181.23160.06850.63820.135*
C191.1478 (4)0.1245 (9)0.6656 (4)0.114 (2)
H191.12730.18450.62700.137*
C201.1151 (3)0.1078 (8)0.7156 (3)0.0910 (18)
H201.07340.15820.71230.109*
C210.8845 (2)0.1519 (5)0.9392 (2)0.0488 (10)
C220.8578 (3)0.3149 (5)0.9190 (3)0.0614 (12)
H22A0.87480.35010.88170.074*
H22B0.87640.38510.95730.074*
C230.7524 (5)0.3137 (9)0.9450 (6)0.1331 (14)
C240.7841 (5)0.2765 (8)1.0120 (6)0.1331 (14)
H240.83150.25871.02800.160*
C250.7418 (5)0.2668 (9)1.0547 (5)0.1331 (14)
H250.76070.24301.10080.160*
C260.6726 (5)0.2924 (9)1.0290 (5)0.1331 (14)
H260.64560.27981.05850.160*
C270.6397 (5)0.3355 (9)0.9627 (5)0.1331 (14)
H270.59290.36020.94820.160*
C280.6798 (5)0.3396 (9)0.9199 (5)0.1331 (14)
H280.65980.35960.87360.160*
C290.9694 (2)0.4992 (5)1.0864 (2)0.0496 (10)
C300.9490 (3)0.4457 (6)1.1472 (2)0.0616 (12)
H30A0.90020.46581.14010.074*
H30B0.95660.33341.15330.074*
C310.9746 (3)0.4884 (5)1.2657 (2)0.0601 (12)
C320.9278 (3)0.3789 (7)1.2719 (3)0.0795 (16)
H320.90170.32401.23380.095*
C330.9198 (4)0.3510 (9)1.3347 (3)0.112 (2)
H330.88890.27441.33980.135*
C340.9567 (4)0.4341 (10)1.3900 (3)0.111 (2)
H340.94950.41731.43230.133*
C351.0043 (4)0.5418 (8)1.3836 (3)0.097 (2)
H351.03040.59601.42200.117*
C361.0140 (3)0.5705 (7)1.3218 (2)0.0781 (15)
H361.04640.64401.31730.094*
H4A0.9596 (19)0.594 (4)1.201 (2)0.077 (16)*
H3A1.0989 (18)0.087 (3)0.8058 (18)0.072 (13)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
La10.04693 (14)0.03354 (14)0.03245 (13)0.00155 (10)0.00435 (9)0.00056 (9)
O10.0534 (16)0.0401 (17)0.0504 (16)0.0001 (14)0.0028 (13)0.0038 (13)
O20.0527 (18)0.0581 (19)0.0478 (17)0.0034 (14)0.0019 (13)0.0077 (14)
O30.0655 (19)0.0530 (18)0.0415 (15)0.0084 (16)0.0167 (13)0.0028 (13)
O40.0778 (19)0.0390 (16)0.0423 (15)0.0064 (15)0.0149 (14)0.0069 (13)
O50.0693 (19)0.0543 (19)0.0450 (16)0.0092 (16)0.0190 (14)0.0116 (14)
O60.094 (2)0.054 (2)0.0431 (16)0.0295 (18)0.0207 (16)0.0028 (14)
N10.054 (2)0.048 (2)0.052 (2)0.0035 (17)0.0059 (17)0.0085 (17)
N20.068 (2)0.043 (2)0.0400 (19)0.0015 (18)0.0015 (16)0.0007 (15)
N30.057 (2)0.063 (3)0.046 (2)0.007 (2)0.0236 (18)0.012 (2)
N50.050 (2)0.035 (2)0.056 (2)0.0143 (15)0.0053 (16)0.0071 (15)
N40.074 (3)0.045 (2)0.0302 (17)0.019 (2)0.0164 (17)0.0054 (15)
C10.065 (3)0.081 (4)0.060 (3)0.007 (3)0.017 (2)0.002 (3)
C20.065 (3)0.120 (6)0.092 (4)0.006 (3)0.033 (3)0.013 (4)
C30.055 (3)0.118 (6)0.117 (6)0.005 (3)0.018 (4)0.017 (4)
C40.057 (3)0.092 (4)0.082 (4)0.008 (3)0.006 (3)0.022 (3)
C50.058 (3)0.043 (3)0.062 (3)0.006 (2)0.003 (2)0.011 (2)
C60.058 (4)0.147 (8)0.113 (6)0.015 (4)0.015 (4)0.024 (5)
C70.083 (5)0.118 (6)0.084 (5)0.039 (4)0.025 (4)0.013 (4)
C80.084 (4)0.067 (3)0.054 (3)0.017 (3)0.017 (3)0.009 (2)
C90.066 (3)0.038 (2)0.053 (3)0.005 (2)0.008 (2)0.003 (2)
C100.123 (5)0.076 (4)0.054 (3)0.017 (4)0.019 (3)0.001 (3)
C110.136 (6)0.077 (4)0.041 (3)0.005 (4)0.001 (3)0.010 (3)
C120.093 (4)0.058 (3)0.051 (3)0.002 (3)0.006 (3)0.009 (2)
C130.061 (3)0.039 (2)0.041 (2)0.004 (2)0.0121 (19)0.0023 (18)
C140.072 (3)0.059 (3)0.050 (3)0.005 (2)0.020 (2)0.011 (2)
C150.079 (3)0.075 (4)0.062 (3)0.006 (3)0.034 (3)0.000 (3)
C160.088 (4)0.104 (5)0.079 (4)0.002 (4)0.042 (3)0.003 (3)
C170.096 (5)0.107 (6)0.124 (6)0.006 (4)0.067 (4)0.005 (5)
C180.155 (7)0.089 (5)0.131 (6)0.015 (5)0.102 (6)0.002 (5)
C190.162 (7)0.109 (5)0.100 (5)0.013 (5)0.082 (5)0.032 (4)
C200.115 (5)0.095 (5)0.082 (4)0.008 (4)0.059 (4)0.025 (3)
C210.053 (2)0.052 (3)0.036 (2)0.003 (2)0.0041 (18)0.0030 (18)
C220.072 (3)0.046 (3)0.059 (3)0.005 (2)0.009 (2)0.005 (2)
C230.149 (3)0.096 (2)0.179 (4)0.015 (2)0.088 (3)0.027 (3)
C240.149 (3)0.096 (2)0.179 (4)0.015 (2)0.088 (3)0.027 (3)
C250.149 (3)0.096 (2)0.179 (4)0.015 (2)0.088 (3)0.027 (3)
C260.149 (3)0.096 (2)0.179 (4)0.015 (2)0.088 (3)0.027 (3)
C270.149 (3)0.096 (2)0.179 (4)0.015 (2)0.088 (3)0.027 (3)
C280.149 (3)0.096 (2)0.179 (4)0.015 (2)0.088 (3)0.027 (3)
C290.067 (3)0.037 (2)0.043 (2)0.002 (2)0.014 (2)0.0020 (18)
C300.081 (3)0.059 (3)0.045 (2)0.020 (3)0.020 (2)0.006 (2)
C310.081 (3)0.059 (3)0.040 (2)0.002 (2)0.017 (2)0.003 (2)
C320.088 (4)0.099 (4)0.055 (3)0.037 (3)0.027 (3)0.004 (3)
C330.134 (6)0.141 (6)0.074 (4)0.054 (5)0.048 (4)0.002 (4)
C340.142 (6)0.147 (7)0.051 (3)0.036 (5)0.041 (4)0.003 (4)
C350.127 (5)0.115 (5)0.044 (3)0.019 (4)0.015 (3)0.007 (3)
C360.097 (4)0.080 (4)0.053 (3)0.019 (3)0.015 (3)0.010 (3)
Geometric parameters (Å, º) top
La1—O12.568 (3)C10—H100.9300
La1—O22.815 (3)C11—C121.404 (7)
La1—O2i2.455 (3)C11—H110.9300
La1—O32.463 (3)C12—H120.9300
La1—O42.399 (3)C13—C141.490 (6)
La1—O5i2.497 (3)C14—H14A0.9700
La1—O6ii2.532 (3)C14—H14B0.9700
La1—N12.756 (4)C15—C161.361 (7)
La1—N22.703 (3)C15—C201.362 (7)
O1—C211.247 (5)C16—C171.362 (8)
O2—C211.276 (5)C16—H160.9300
O2—La1i2.455 (3)C17—C181.348 (10)
O3—C131.263 (5)C17—H170.9300
O4—C291.254 (5)C18—C191.359 (9)
O5—C131.245 (5)C18—H180.9300
O5—La1i2.497 (3)C19—C201.377 (8)
O6—C291.223 (5)C19—H190.9300
O6—La1ii2.532 (3)C20—H200.9300
N1—C11.307 (6)C21—C221.502 (6)
N1—C51.353 (6)C22—H22A0.9700
N2—C121.311 (6)C22—H22B0.9700
N2—C91.361 (6)C23—C241.372 (13)
N3—C151.359 (6)C23—C281.424 (13)
N3—C141.430 (6)C24—C251.391 (11)
N3—H3A0.771 (18)C24—H240.9300
N5—C231.310 (10)C25—C261.363 (12)
N5—C221.408 (6)C25—H250.9300
N5—H5A0.8600C26—C271.377 (12)
N4—C311.352 (5)C26—H260.9300
N4—C301.413 (5)C27—C281.356 (10)
N4—H4A0.80 (4)C27—H270.9300
C1—C21.400 (7)C28—H280.9300
C1—H10.9300C29—C301.491 (6)
C2—C31.365 (9)C30—H30A0.9700
C2—H20.9300C30—H30B0.9700
C3—C41.360 (9)C31—C321.359 (7)
C3—H30.9300C31—C361.382 (7)
C4—C51.428 (7)C32—C331.361 (7)
C4—C61.479 (9)C32—H320.9300
C5—C91.410 (7)C33—C341.359 (9)
C6—C71.287 (10)C33—H330.9300
C6—H60.9300C34—C351.361 (9)
C7—C81.437 (9)C34—H340.9300
C7—H70.9300C35—C361.357 (7)
C8—C101.375 (8)C35—H350.9300
C8—C91.412 (6)C36—H360.9300
C10—C111.366 (8)
O1—La1—O248.23 (8)C12—C11—H11120.2
O1—La1—O373.64 (9)N2—C12—C11121.8 (6)
O1—La1—O4138.93 (10)N2—C12—H12119.1
O2—La1—O364.58 (9)C11—C12—H12119.1
O2—La1—O4140.15 (9)O5—C13—O3128.7 (4)
O3—La1—O4145.72 (10)O5—C13—C14118.8 (4)
O1—La1—N163.25 (10)O3—C13—C14112.5 (4)
O2—La1—N1102.50 (10)N3—C14—C13110.6 (4)
O3—La1—N1127.37 (10)N3—C14—H14A109.5
O4—La1—N177.38 (10)C13—C14—H14A109.5
O1—La1—N273.99 (10)N3—C14—H14B109.5
O2—La1—N2118.24 (9)C13—C14—H14B109.5
O3—La1—N281.95 (10)H14A—C14—H14B108.1
O4—La1—N296.14 (10)C13—C14—H3A105.8 (14)
N1—La1—N258.89 (11)H14A—C14—H3A84.9
O4—La1—O2i88.13 (10)H14B—C14—H3A134.9
O2i—La1—O377.63 (10)N3—C15—C16114.3 (5)
O4—La1—O5i76.40 (9)N3—C15—C20124.0 (5)
O2i—La1—O5i74.63 (9)C16—C15—C20121.7 (5)
O3—La1—O5i127.52 (10)C15—C16—C17119.7 (6)
O4—La1—O6ii76.42 (10)C15—C16—H16120.1
O2i—La1—O6ii77.68 (10)C17—C16—H16120.1
O3—La1—O6ii70.18 (10)C18—C17—C16119.5 (7)
O5i—La1—O6ii141.46 (10)C18—C17—H17120.2
O2i—La1—O1120.86 (10)C16—C17—H17120.2
O5i—La1—O183.77 (9)C17—C18—C19120.8 (6)
O6ii—La1—O1134.00 (9)C17—C18—H18119.6
O2i—La1—N2149.12 (11)C19—C18—H18119.6
O5i—La1—N2136.11 (11)C18—C19—C20120.7 (7)
O6ii—La1—N273.70 (11)C18—C19—H19119.7
O2i—La1—N1150.82 (10)C20—C19—H19119.7
O5i—La1—N177.38 (10)C15—C20—C19117.5 (6)
O6ii—La1—N1121.95 (12)C15—C20—H20121.2
O2i—La1—O272.85 (11)C19—C20—H20121.2
O5i—La1—O265.03 (9)O1—C21—O2122.4 (4)
O6ii—La1—O2129.92 (10)O1—C21—C22119.9 (4)
C21—O1—La1100.8 (2)O2—C21—C22117.7 (4)
C21—O2—La1i162.7 (3)N5—C22—C21114.3 (4)
C21—O2—La188.4 (2)N5—C22—H22A108.7
La1i—O2—La1107.15 (11)C21—C22—H22A108.7
C13—O3—La1130.0 (2)N5—C22—H22B108.7
C29—O4—La1151.1 (3)C21—C22—H22B108.7
C13—O5—La1i137.6 (3)H22A—C22—H22B107.6
C29—O6—La1ii150.0 (3)N5—C23—C24123.6 (10)
C1—N1—C5117.4 (4)N5—C23—C28114.3 (10)
C1—N1—La1120.0 (3)C24—C23—C28122.1 (9)
C5—N1—La1121.0 (3)C23—C24—C25116.5 (10)
C12—N2—C9118.2 (4)C23—C24—H24121.7
C12—N2—La1118.9 (3)C25—C24—H24121.7
C9—N2—La1122.6 (3)C26—C25—C24119.9 (10)
C15—N3—C14116.8 (4)C26—C25—H25120.1
C15—N3—H3A94 (3)C24—C25—H25120.1
C14—N3—H3A84 (3)C25—C26—C27124.9 (9)
C23—N5—C22118.8 (6)C25—C26—H26117.5
C23—N5—H5A120.6C27—C26—H26117.5
C22—N5—H5A120.6C28—C27—C26115.7 (10)
C31—N4—C30116.6 (4)C28—C27—H27122.1
C31—N4—H4A89 (3)C26—C27—H27122.1
C30—N4—H4A92 (3)C27—C28—C23120.7 (10)
N1—C1—C2123.2 (5)C27—C28—H28119.7
N1—C1—H1118.4C23—C28—H28119.7
C2—C1—H1118.4O6—C29—O4128.2 (4)
C3—C2—C1119.6 (6)O6—C29—C30119.8 (4)
C3—C2—H2120.2O4—C29—C30111.8 (4)
C1—C2—H2120.2N4—C30—C29110.4 (4)
C4—C3—C2119.5 (6)N4—C30—H30A109.6
C4—C3—H3120.3C29—C30—H30A109.6
C2—C3—H3120.3N4—C30—H30B109.6
C3—C4—C5117.6 (5)C29—C30—H30B109.6
C3—C4—C6123.9 (6)H30A—C30—H30B108.1
C5—C4—C6118.5 (6)N4—C31—C32124.7 (4)
N1—C5—C9117.6 (4)N4—C31—C36114.1 (4)
N1—C5—C4122.7 (5)C32—C31—C36121.2 (5)
C9—C5—C4119.7 (5)C32—C31—H4A120.4 (18)
C7—C6—C4121.2 (7)C36—C31—H4A109.8 (18)
C7—C6—H6119.4C31—C32—C33118.9 (5)
C4—C6—H6119.4C31—C32—H32120.5
C6—C7—C8120.6 (6)C33—C32—H32120.5
C6—C7—H7119.7C34—C33—C32120.5 (6)
C8—C7—H7119.7C34—C33—H33119.7
C10—C8—C9116.1 (6)C32—C33—H33119.7
C10—C8—C7122.4 (6)C33—C34—C35120.2 (5)
C9—C8—C7121.5 (6)C33—C34—H34119.9
N2—C9—C5118.3 (4)C35—C34—H34119.9
N2—C9—C8123.5 (5)C36—C35—C34120.4 (6)
C5—C9—C8118.2 (5)C36—C35—H35119.8
C11—C10—C8120.6 (5)C34—C35—H35119.8
C11—C10—H10119.7C35—C36—C31118.7 (5)
C8—C10—H10119.7C35—C36—H36120.7
C10—C11—C12119.6 (6)C31—C36—H36120.7
C10—C11—H11120.2
Symmetry codes: (i) x+2, y, z+2; (ii) x+2, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O5i0.932.463.147 (6)131
C10—H10···O1iii0.932.313.177 (6)156
C12—H12···O6ii0.932.463.061 (6)123
C12—H12···N4ii0.932.593.439 (7)152
C22—H22B···O4iv0.972.383.328 (6)165
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, y1, z.

Experimental details

Crystal data
Chemical formula[La2(C8H8NO2)6(C12H8N2)2]
Mr1539.16
Crystal system, space groupMonoclinic, P21/n
Temperature (K)273
a, b, c (Å)20.2217 (15), 8.5007 (18), 20.449 (3)
β (°) 106.801 (3)
V3)3365.1 (9)
Z2
Radiation typeMo Kα
µ (mm1)1.32
Crystal size (mm)0.32 × 0.13 × 0.08
Data collection
DiffractometerBruker APEX-II area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.674, 0.900
No. of measured, independent and
observed [I > 2σ(I)] reflections
24428, 6591, 4615
Rint0.040
(sin θ/λ)max1)0.620
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.038, 0.100, 0.96
No. of reflections6591
No. of parameters411
No. of restraints5
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.36, 0.54

Computer programs: APEX2 (Bruker, 2005), SAINT (Siemens, 1996), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996), SHELXTL.

Selected geometric parameters (Å, º) top
La1—O12.568 (3)La1—O5i2.497 (3)
La1—O22.815 (3)La1—O6ii2.532 (3)
La1—O2i2.455 (3)La1—N12.756 (4)
La1—O32.463 (3)La1—N22.703 (3)
La1—O42.399 (3)
O1—La1—O248.23 (8)O3—La1—N1127.37 (10)
O1—La1—O373.64 (9)O4—La1—N177.38 (10)
O1—La1—O4138.93 (10)O1—La1—N273.99 (10)
O2—La1—O364.58 (9)O2—La1—N2118.24 (9)
O2—La1—O4140.15 (9)O3—La1—N281.95 (10)
O3—La1—O4145.72 (10)O4—La1—N296.14 (10)
O1—La1—N163.25 (10)N1—La1—N258.89 (11)
O2—La1—N1102.50 (10)
Symmetry codes: (i) x+2, y, z+2; (ii) x+2, y+1, z+2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C1—H1···O5i0.932.463.147 (6)131
C10—H10···O1iii0.932.313.177 (6)156
C12—H12···O6ii0.932.463.061 (6)123
C12—H12···N4ii0.932.593.439 (7)152
C22—H22B···O4iv0.972.383.328 (6)165
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, y1, z.
 

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