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Acta Cryst. (2007). E63, m2020-m2021    [ doi:10.1107/S1600536807030917 ]

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

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

Abstract top

The molecule of the title compound, [La2(C7H6NO3)6(C12H8N2)2], has an inversion centre midway between the two LaIII 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.

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 LaIII 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.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93 and 0.97 Å for aromatic and methylene H atoms, and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

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
[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 [symmetry code (A): 2 - x, -y, 2 - z].
[Figure 2] 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
Mr = 1551.00Dx = 1.456 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9025 reflections
a = 20.312 (3) Åθ = 2.4–26.7°
b = 8.721 (2) ŵ = 1.26 mm−1
c = 20.915 (3) ÅT = 273 K
β = 107.332 (9)°Plate, colorless
V = 3536.8 (11) Å30.33 × 0.13 × 0.08 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer		7585 independent reflections
Radiation source: fine-focus sealed tube5008 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
φ and ω scansθmax = 27.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −25→25
Tmin = 0.682, Tmax = 0.905k = −10→11
27369 measured reflectionsl = −26→26
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.05P)2 + 0.9707P]
where P = (Fo2 + 2Fc2)/3
7585 reflections(Δ/σ)max = 0.001
403 parametersΔρmax = 0.59 e Å−3
3 restraintsΔρmin = −0.59 e Å−3
Crystal data top
[La2(C7H6NO3)6(C12H8N2)2]V = 3536.8 (11) Å3
Mr = 1551.00Z = 2
Monoclinic, P21/nMo Kα radiation
a = 20.312 (3) ŵ = 1.26 mm−1
b = 8.721 (2) ÅT = 273 K
c = 20.915 (3) Å0.33 × 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)
Tmin = 0.682, Tmax = 0.905Rint = 0.043
27369 measured reflectionsθmax = 27.0°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.099Δρmax = 0.59 e Å−3
S = 1.00Δρmin = −0.59 e Å−3
7585 reflectionsAbsolute structure: ?
403 parametersFlack parameter: ?
3 restraintsRogers parameter: ?
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
La10.931204 (11)0.19063 (2)0.964291 (10)0.04055 (9)
O10.84640 (13)−0.0360 (3)0.91884 (13)0.0525 (7)
O20.94651 (13)−0.1380 (4)0.97709 (13)0.0578 (7)
O30.94005 (14)0.4208 (3)1.03412 (12)0.0560 (7)
O40.97065 (14)0.0599 (3)0.87485 (12)0.0558 (7)
O51.06702 (14)−0.0831 (3)0.92168 (13)0.0577 (7)
O61.11841 (16)−0.0166 (4)0.82197 (15)0.0765 (9)
O70.78448 (16)−0.3265 (3)0.89795 (17)0.0721 (9)
O81.00778 (16)0.6128 (4)1.09096 (13)0.0656 (8)
O90.98699 (16)0.5278 (4)1.20622 (13)0.0711 (9)
N10.79696 (17)0.2345 (4)0.96667 (17)0.0554 (9)
N20.83402 (19)0.3068 (4)0.85441 (16)0.0557 (9)
N31.1133 (3)0.1077 (7)0.7156 (3)0.129 (2)
N40.7868 (4)−0.2775 (7)1.0123 (4)0.1454 (13)
N50.9271 (3)0.3777 (7)1.2705 (2)0.1130 (17)
C10.7780 (2)0.1921 (5)1.0201 (2)0.0710 (13)
H10.81220.16901.05970.085*
C20.7091 (3)0.1811 (7)1.0189 (3)0.0924 (18)
H20.69810.15151.05720.111*
C30.6578 (3)0.2138 (8)0.9613 (4)0.101 (2)
H30.61180.20600.96030.122*
C40.6742 (3)0.2588 (7)0.9043 (3)0.0846 (16)
C50.7460 (2)0.2676 (5)0.9088 (2)0.0595 (11)
C60.6238 (3)0.2977 (9)0.8398 (4)0.120 (3)
H60.57700.28880.83540.144*
C70.6427 (3)0.3450 (8)0.7875 (3)0.112 (2)
H70.60900.37260.74820.135*
C80.7133 (3)0.3542 (6)0.7904 (3)0.0787 (15)
C90.7658 (2)0.3096 (5)0.8505 (2)0.0588 (11)
C100.7356 (4)0.4030 (7)0.7365 (3)0.0950 (19)
H100.70340.43710.69750.114*
C110.8032 (4)0.4012 (6)0.7407 (2)0.0903 (17)
H110.81770.43360.70460.108*
C120.8524 (3)0.3489 (5)0.8009 (2)0.0711 (13)
H120.89870.34410.80280.085*
C130.8843 (2)−0.1512 (5)0.93930 (19)0.0505 (10)
C140.8576 (2)−0.3145 (5)0.9191 (2)0.0623 (11)
H14A0.8749−0.34900.88300.075*
H14B0.8761−0.38240.95690.075*
C150.7509 (6)−0.3132 (8)0.9433 (5)0.1454 (13)
C160.6798 (5)−0.3380 (8)0.9209 (5)0.1454 (13)
H160.6584−0.35800.87580.174*
C170.6412 (5)−0.3333 (8)0.9649 (5)0.1454 (13)
H170.5945−0.35820.95100.174*
C180.6736 (5)−0.2903 (8)1.0307 (5)0.1454 (13)
H180.6464−0.27891.05910.174*
C190.7428 (5)−0.2636 (9)1.0565 (5)0.1454 (13)
H190.7616−0.23711.10130.174*
C200.9691 (2)0.4992 (5)1.08642 (19)0.0505 (10)
C210.9490 (2)0.4459 (5)1.14740 (19)0.0650 (12)
H21A0.90000.46231.13970.078*
H21B0.95810.33701.15410.078*
C220.9751 (2)0.4892 (5)1.2657 (2)0.0617 (11)
C231.0144 (3)0.5693 (6)1.3220 (2)0.0795 (15)
H231.04690.64081.31800.095*
C241.0047 (3)0.5416 (8)1.3834 (2)0.1020 (19)
H241.03040.59541.42100.122*
C250.9566 (4)0.4332 (9)1.3894 (3)0.115 (2)
H250.94940.41671.43080.138*
C260.9201 (4)0.3518 (9)1.3352 (3)0.119 (3)
H260.88950.27681.34050.142*
C271.0287 (2)0.0032 (5)0.87717 (19)0.0491 (9)
C281.0526 (2)0.0503 (5)0.8173 (2)0.0637 (12)
H28B1.01900.01700.77610.076*
H28A1.05600.16110.81590.076*
C291.1458 (3)0.0143 (6)0.7707 (2)0.0697 (13)
C301.2082 (3)−0.0548 (7)0.7764 (3)0.0895 (16)
H301.2292−0.11480.81360.107*
C311.2398 (3)−0.0351 (8)0.7264 (4)0.106 (2)
H311.2817−0.08310.73000.127*
C321.2096 (4)0.0547 (8)0.6720 (4)0.114 (2)
H321.23120.06790.63890.136*
C331.1486 (4)0.1242 (8)0.6661 (3)0.119 (2)
H331.12900.18470.62860.142*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
La10.04671 (13)0.03586 (13)0.03402 (12)−0.00164 (11)0.00427 (8)0.00055 (10)
O10.0531 (15)0.0420 (17)0.0535 (16)0.0007 (13)0.0023 (12)−0.0036 (12)
O20.0511 (17)0.0636 (19)0.0493 (16)−0.0041 (13)0.0005 (13)0.0072 (13)
O30.0775 (19)0.0429 (16)0.0449 (15)−0.0070 (15)0.0142 (13)−0.0061 (13)
O40.0648 (18)0.0573 (18)0.0446 (15)0.0085 (15)0.0152 (13)0.0023 (13)
O50.0684 (18)0.0585 (19)0.0466 (16)0.0088 (15)0.0178 (13)0.0117 (14)
O60.077 (2)0.096 (3)0.064 (2)0.0207 (19)0.0335 (17)0.0231 (18)
O70.067 (2)0.055 (2)0.079 (2)−0.0157 (15)−0.0016 (16)−0.0073 (16)
O80.094 (2)0.0575 (19)0.0445 (16)−0.0287 (18)0.0195 (15)−0.0028 (14)
O90.099 (2)0.072 (2)0.0426 (16)−0.0303 (18)0.0207 (15)−0.0074 (14)
N10.055 (2)0.051 (2)0.053 (2)0.0033 (16)0.0047 (17)−0.0081 (16)
N20.069 (2)0.045 (2)0.0430 (19)0.0038 (17)0.0015 (16)0.0007 (16)
N30.166 (5)0.136 (5)0.106 (4)−0.003 (4)0.075 (4)0.026 (4)
N40.171 (4)0.110 (2)0.186 (4)0.018 (2)0.100 (3)0.030 (3)
N50.117 (4)0.135 (5)0.096 (4)−0.033 (4)0.046 (3)0.008 (3)
C10.065 (3)0.087 (4)0.060 (3)0.007 (3)0.017 (2)−0.003 (3)
C20.066 (3)0.129 (5)0.088 (4)0.004 (3)0.033 (3)−0.014 (4)
C30.052 (3)0.133 (6)0.116 (5)−0.002 (3)0.020 (3)−0.019 (4)
C40.052 (3)0.097 (4)0.085 (4)0.008 (3)−0.008 (3)−0.021 (3)
C50.056 (3)0.047 (3)0.066 (3)0.006 (2)0.004 (2)−0.011 (2)
C60.064 (4)0.159 (8)0.111 (5)0.015 (4)−0.012 (4)−0.032 (5)
C70.082 (4)0.128 (6)0.090 (5)0.041 (4)−0.030 (3)−0.018 (4)
C80.082 (4)0.070 (3)0.059 (3)0.018 (3)−0.018 (3)−0.011 (2)
C90.064 (3)0.042 (2)0.052 (2)0.005 (2)−0.0114 (19)−0.005 (2)
C100.118 (5)0.082 (4)0.055 (3)0.020 (4)−0.021 (3)0.002 (3)
C110.130 (5)0.081 (4)0.044 (3)0.001 (4)0.001 (3)0.012 (3)
C120.092 (4)0.062 (3)0.050 (3)−0.003 (3)0.006 (2)0.009 (2)
C130.054 (2)0.056 (3)0.037 (2)−0.003 (2)0.0061 (17)−0.0027 (18)
C140.067 (3)0.051 (3)0.062 (3)0.004 (2)0.007 (2)−0.006 (2)
C150.171 (4)0.110 (2)0.186 (4)0.018 (2)0.100 (3)0.030 (3)
C160.171 (4)0.110 (2)0.186 (4)0.018 (2)0.100 (3)0.030 (3)
C170.171 (4)0.110 (2)0.186 (4)0.018 (2)0.100 (3)0.030 (3)
C180.171 (4)0.110 (2)0.186 (4)0.018 (2)0.100 (3)0.030 (3)
C190.171 (4)0.110 (2)0.186 (4)0.018 (2)0.100 (3)0.030 (3)
C200.067 (3)0.039 (2)0.045 (2)−0.004 (2)0.0145 (19)0.0012 (18)
C210.084 (3)0.063 (3)0.049 (2)−0.021 (3)0.021 (2)−0.006 (2)
C220.078 (3)0.063 (3)0.045 (2)−0.007 (2)0.021 (2)0.004 (2)
C230.098 (4)0.086 (4)0.052 (3)−0.024 (3)0.017 (2)−0.010 (3)
C240.130 (5)0.121 (5)0.047 (3)−0.024 (4)0.013 (3)−0.010 (3)
C250.144 (6)0.154 (7)0.057 (3)−0.032 (5)0.043 (4)0.008 (4)
C260.140 (6)0.160 (7)0.067 (4)−0.067 (5)0.048 (4)−0.002 (4)
C270.061 (3)0.042 (2)0.043 (2)−0.003 (2)0.0134 (19)−0.0015 (18)
C280.073 (3)0.065 (3)0.055 (3)0.007 (2)0.023 (2)0.014 (2)
C290.081 (3)0.075 (3)0.063 (3)−0.004 (3)0.038 (3)0.005 (2)
C300.090 (4)0.110 (5)0.081 (4)0.002 (4)0.044 (3)0.002 (3)
C310.101 (4)0.114 (6)0.126 (5)−0.005 (4)0.069 (4)−0.009 (4)
C320.152 (6)0.096 (5)0.131 (6)−0.015 (5)0.100 (5)0.001 (4)
C330.169 (7)0.117 (5)0.103 (5)0.016 (5)0.091 (5)0.033 (4)
Geometric parameters (Å, º) top
La1—O12.608 (3)C6—H60.9300
La1—O22.887 (3)C7—C81.420 (9)
La1—O32.457 (3)C7—H70.9300
La1—O42.517 (3)C8—C101.400 (8)
La1—N12.769 (3)C8—C91.438 (6)
La1—N22.739 (3)C10—C111.351 (8)
La1—O2i2.463 (3)C10—H100.9300
La1—O5i2.553 (3)C11—C121.429 (6)
La1—O8ii2.581 (3)C11—H110.9300
O1—C131.260 (5)C12—H120.9300
O2—C131.280 (5)C13—C141.538 (6)
O2—La1i2.463 (3)C14—H14A0.9700
O3—C201.276 (4)C14—H14B0.9700
O4—C271.266 (4)C15—C161.396 (12)
O5—C271.268 (4)C16—C171.377 (10)
O5—La1i2.553 (3)C16—H160.9300
O6—C291.373 (5)C17—C181.388 (12)
O6—C281.435 (5)C17—H170.9300
O7—C151.329 (9)C18—C191.366 (11)
O7—C141.422 (5)C18—H180.9300
O8—C201.251 (5)C19—H190.9300
O8—La1ii2.581 (3)C20—C211.523 (5)
O9—C221.377 (5)C21—H21A0.9700
O9—C211.433 (5)C21—H21B0.9700
N1—C11.338 (5)C22—C231.397 (6)
N1—C51.369 (5)C23—C241.378 (7)
N2—C121.333 (5)C23—H230.9300
N2—C91.363 (6)C24—C251.393 (8)
N3—C291.406 (7)C24—H240.9300
N3—C331.432 (7)C25—C261.357 (8)
N4—C151.444 (11)C25—H250.9300
N4—C191.470 (9)C26—H260.9300
N5—C221.403 (6)C27—C281.529 (5)
N5—C261.420 (7)C28—H28B0.9700
C1—C21.396 (7)C28—H28A0.9700
C1—H10.9300C29—C301.376 (7)
C2—C31.370 (8)C30—C311.391 (7)
C2—H20.9300C30—H300.9300
C3—C41.387 (8)C31—C321.366 (9)
C3—H30.9300C31—H310.9300
C4—C51.436 (7)C32—C331.351 (9)
C4—C61.470 (8)C32—H320.9300
C5—C91.441 (6)C33—H330.9300
C6—C71.328 (9)
O1—La1—O247.35 (8)C8—C9—C5119.1 (5)
O1—La1—O3139.39 (9)C11—C10—C8120.8 (5)
O1—La1—O473.00 (9)C11—C10—H10119.6
O2—La1—O3140.28 (8)C8—C10—H10119.6
O2—La1—O464.52 (8)C10—C11—C12119.4 (5)
O3—La1—O4145.97 (9)C10—C11—H11120.3
O1—La1—N164.18 (9)C12—C11—H11120.3
O2—La1—N1102.42 (9)N2—C12—C11122.0 (5)
O3—La1—N176.96 (10)N2—C12—H12119.0
O4—La1—N1127.54 (9)C11—C12—H12119.0
O1—La1—N275.05 (9)O1—C13—O2121.9 (4)
O2—La1—N2118.42 (8)O1—C13—C14121.0 (4)
O3—La1—N295.92 (9)O2—C13—C14117.1 (4)
O4—La1—N281.57 (9)O7—C14—C13113.8 (3)
N1—La1—N259.76 (11)O7—C14—H14A108.8
O3—La1—O2i88.40 (10)C13—C14—H14A108.8
O2i—La1—O477.79 (9)O7—C14—H14B108.8
O3—La1—O5i76.50 (9)C13—C14—H14B108.8
O2i—La1—O5i74.64 (9)H14A—C14—H14B107.7
O4—La1—O5i127.51 (9)O7—C15—C16116.5 (10)
O3—La1—O8ii76.33 (9)O7—C15—N4121.3 (9)
O2i—La1—O8ii78.41 (10)C16—C15—N4122.2 (8)
O4—La1—O8ii70.52 (9)C17—C16—C15120.7 (10)
O5i—La1—O8ii141.91 (9)C17—C16—H16119.7
O2i—La1—O1119.91 (10)C15—C16—H16119.7
O5i—La1—O183.46 (9)C16—C17—C18118.2 (10)
O8ii—La1—O1133.88 (8)C16—C17—H17120.9
O2i—La1—N2148.68 (10)C18—C17—H17120.9
O5i—La1—N2136.54 (10)C19—C18—C17124.6 (9)
O8ii—La1—N272.59 (10)C19—C18—H18117.7
O2i—La1—N1150.37 (10)C17—C18—H18117.7
O5i—La1—N176.93 (10)C18—C19—N4118.9 (9)
O8ii—La1—N1121.53 (11)C18—C19—H19120.5
O2i—La1—O272.79 (10)N4—C19—H19120.5
O5i—La1—O265.01 (8)O8—C20—O3127.5 (4)
O8ii—La1—O2130.39 (9)O8—C20—C21119.8 (4)
C13—O1—La1102.1 (2)O3—C20—C21112.6 (3)
C13—O2—La1i162.5 (3)O9—C21—C20110.9 (3)
C13—O2—La188.4 (2)O9—C21—H21A109.5
La1i—O2—La1107.21 (10)C20—C21—H21A109.5
C20—O3—La1151.7 (3)O9—C21—H21B109.5
C27—O4—La1130.4 (2)C20—C21—H21B109.5
C27—O5—La1i137.6 (3)H21A—C21—H21B108.0
C29—O6—C28116.9 (3)O9—C22—C23115.4 (4)
C15—O7—C14118.9 (6)O9—C22—N5123.2 (4)
C20—O8—La1ii150.1 (3)C23—C22—N5121.4 (4)
C22—O9—C21117.3 (3)C24—C23—C22119.6 (5)
C1—N1—C5117.9 (4)C24—C23—H23120.2
C1—N1—La1120.4 (3)C22—C23—H23120.2
C5—N1—La1120.1 (3)C23—C24—C25120.2 (5)
C12—N2—C9118.6 (4)C23—C24—H24119.9
C12—N2—La1119.6 (3)C25—C24—H24119.9
C9—N2—La1121.5 (3)C26—C25—C24120.2 (5)
C29—N3—C33116.0 (6)C26—C25—H25119.9
C15—N4—C19115.2 (8)C24—C25—H25119.9
C22—N5—C26116.7 (5)C25—C26—N5121.9 (6)
N1—C1—C2122.7 (5)C25—C26—H26119.1
N1—C1—H1118.6N5—C26—H26119.1
C2—C1—H1118.6O4—C27—O5128.4 (4)
C3—C2—C1119.9 (5)O4—C27—C28112.5 (3)
C3—C2—H2120.1O5—C27—C28119.1 (4)
C1—C2—H2120.1O6—C28—C27110.6 (3)
C2—C3—C4120.1 (5)O6—C28—H28B109.5
C2—C3—H3120.0C27—C28—H28B109.5
C4—C3—H3120.0O6—C28—H28A109.5
C3—C4—C5117.3 (5)C27—C28—H28A109.5
C3—C4—C6125.0 (6)H28B—C28—H28A108.1
C5—C4—C6117.7 (6)O6—C29—C30115.1 (4)
N1—C5—C4122.1 (5)O6—C29—N3123.6 (5)
N1—C5—C9118.3 (4)C30—C29—N3121.3 (5)
C4—C5—C9119.5 (4)C29—C30—C31120.1 (6)
C7—C6—C4122.3 (6)C29—C30—H30119.9
C7—C6—H6118.8C31—C30—H30120.0
C4—C6—H6118.8C32—C31—C30120.2 (6)
C6—C7—C8121.2 (6)C32—C31—H31119.9
C6—C7—H7119.4C30—C31—H31119.9
C8—C7—H7119.4C33—C32—C31120.4 (6)
C10—C8—C7123.2 (5)C33—C32—H32119.8
C10—C8—C9116.8 (5)C31—C32—H32119.8
C7—C8—C9120.0 (6)C32—C33—N3122.1 (6)
N2—C9—C8122.3 (5)C32—C33—H33119.0
N2—C9—C5118.6 (3)N3—C33—H33119.0
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
C10—H10···O1iii0.932.353.224 (6)156
C14—H14B···O3iv0.972.453.394 (5)165
C12—H12···O8ii0.932.483.076 (6)122
C1—H1···O5i0.932.483.163 (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.
Selected geometric parameters (Å, º) top
La1—O12.608 (3)La1—O42.517 (3)
La1—O22.887 (3)La1—N12.769 (3)
La1—O32.457 (3)La1—N22.739 (3)
O1—La1—O247.35 (8)O3—La1—N176.96 (10)
O1—La1—O3139.39 (9)O4—La1—N1127.54 (9)
O1—La1—O473.00 (9)O1—La1—N275.05 (9)
O2—La1—O3140.28 (8)O2—La1—N2118.42 (8)
O2—La1—O464.52 (8)O3—La1—N295.92 (9)
O3—La1—O4145.97 (9)O4—La1—N281.57 (9)
O1—La1—N164.18 (9)N1—La1—N259.76 (11)
O2—La1—N1102.42 (9)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O1i0.932.353.224 (6)156
C14—H14B···O3ii0.972.453.394 (5)165
C12—H12···O8iii0.932.483.076 (6)122
C1—H1···O5iv0.932.483.163 (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.
Acknowledgements top

We thank the Youth Program of Jinggangshan University for financial support of this work.

references
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