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Acta Cryst. (2009). E65, m59    [ doi:10.1107/S1600536808038075 ]

Bis([mu]-N-acetyl-N-phenylglycinato-[kappa]2O:O')bis[dinitrato-[kappa]4O,O'-bis(1,10-phenanthroline-[kappa]2N,N')lanthanum(III)]

X. Gao

Abstract top

In the title complex, [La2(C10H10NO3)2(NO3)4(C12H8N2)4], each LaIII ion is ten-coordinated by four N atoms from two bidentate 1,10-phenanthroline ligands and by six O atoms, two from the N-acetyl-N-phenylglycinate ligands and four from two nitrate anions. Two LaIII cations, which exhibit a distorted bicapped square-antiprismatic coordination, are bridged by two N-acetyl-N-phenylglycinate ligands into a dimeric structure, generated by inversion symmetry. There is a [pi]-[pi] contact between the benzene rings [centroid-centroid distance = 3.409 (3) Å].

Comment top

N-acetyl-N-phenylglycinate should be a very useful multidentate ligand and may act as bridge ligand due to coordination of its acetyl O and carboxylate O atoms. A few multinuclear complexes have been synthesized with monodeprotonated N-acetyl-N-phenylglycinate as bridge ligand (Fu et al. 2004a,b). We were interested in synthesizing multinuclear complexes with they as bridge ligands, and obtained the title dinuclear complex. We reported herein its crystal structure.

The coordination structure of the title complex is shown in Fig. 1. In the dinuclear complex, each LaIII ion is ten-coordinated by atoms N2, N3, N4 and N5 from two 1,10-phenanthroline (L2) ligands, atoms O4, O5, O7 and O8 from two nitrate anions (L3), atoms O1, O2i [symmetry code: (i) 2 - x, 2 - y, 2 - z] from carboxylate groups of two N-acetyl-N-phenylglycinate (L1) ligands. The coordination sphere around La is a distorted bicapped square-antiprism, with the capping positions occupied by atoms O5 of nitrate anion and O7 of another nitrate anion. The coordinated L1 ligand bonds to two La via two O atoms of carboxylate group, thus acting as a bridge. The overall complex has inversion symmetry. The π–π contact between the benzene rings, Cg1···Cg1ii [symmetry code: (ii) x - 1, y, z - 1, where Cg1 is the centroid of the ring (C14–C17/C21/C22)] may stabilize the structure, with centroid–centroid distance of 3.409 (3) Å.

Related literature top

For related structures, see: Fu et al. (2004a,b).

Experimental top

La(NO3)3.nH2O (1 mmol) and 1,10-phenanthroline (1 mmol) were dissolved in anhydrous ethanol (20 ml). To this solution, an aqueous mixture (10 ml) of N-acetyl-N-phenylglycinate (1 mmol) and NaOH (1 mmol) was added dropwise. The mixture was stirred for 2 h. The large yellow crystals were obtained after the solution had been allowed to stand at room temperature for three weeks.

Refinement top

H atoms were positioned geometrically, with C—H = 0.93, 0.97 and 0.96 Å for aromatic, methylene and methyl H, respectively, and constrained to ride on their parent atoms with Uiso(H) = xUeq(C), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

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: (i) 2 - x, 2 - y, 2 - z].
Bis(µ-N-acetyl-N-phenylglycinato- κ2O:O')bis[dinitrato-κ4O,O'-bis(1,10- phenanthroline-κ2N,N')lanthanum(III)] top
Crystal data top
[La2(C10H10NO3)2(NO3)4(C12H8N2)4]F(000) = 1632
Mr = 1631.06Dx = 1.670 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6044 reflections
a = 14.0891 (7) Åθ = 2.3–27.5°
b = 13.7610 (7) ŵ = 1.39 mm−1
c = 16.9962 (9) ÅT = 296 K
β = 100.121 (1)°Needle, yellow
V = 3243.9 (3) Å30.45 × 0.43 × 0.40 mm
Z = 2
Data collection top
Bruker SMART CCD area-detector
diffractometer		5719 independent reflections
Radiation source: fine-focus sealed tube4467 reflections with I > 2σ(I)
graphiteRint = 0.031
φ and ω scansθmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −15→16
Tmin = 0.574, Tmax = 0.543k = −16→12
16038 measured reflectionsl = −20→15
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)] = 0.025Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.059H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0228P)2 + 0.722P]
where P = (Fo2 + 2Fc2)/3
5719 reflections(Δ/σ)max = 0.002
461 parametersΔρmax = 0.70 e Å−3
0 restraintsΔρmin = −0.42 e Å−3
Crystal data top
[La2(C10H10NO3)2(NO3)4(C12H8N2)4]V = 3243.9 (3) Å3
Mr = 1631.06Z = 2
Monoclinic, P21/nMo Kα radiation
a = 14.0891 (7) ŵ = 1.39 mm−1
b = 13.7610 (7) ÅT = 296 K
c = 16.9962 (9) Å0.45 × 0.43 × 0.40 mm
β = 100.121 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		5719 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		4467 reflections with I > 2σ(I)
Tmin = 0.574, Tmax = 0.543Rint = 0.031
16038 measured reflectionsθmax = 25.0°
Refinement top
R[F2 > 2σ(F2)] = 0.025H-atom parameters constrained
wR(F2) = 0.059Δρmax = 0.70 e Å−3
S = 1.06Δρmin = −0.42 e Å−3
5719 reflectionsAbsolute structure: ?
461 parametersFlack parameter: ?
0 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
La10.845573 (12)0.870851 (12)0.945459 (10)0.02900 (6)
N11.13333 (19)0.8679 (2)0.79326 (15)0.0430 (7)
N20.90459 (18)0.70723 (18)0.87965 (14)0.0359 (6)
N30.99585 (18)0.77290 (18)1.02680 (15)0.0367 (6)
N40.66037 (18)0.79638 (19)0.89767 (15)0.0379 (6)
N50.68663 (18)0.98664 (18)0.94152 (15)0.0375 (6)
N60.80835 (19)0.9726 (2)0.78155 (17)0.0428 (7)
N70.8123 (2)0.7497 (2)1.08954 (18)0.0495 (8)
O10.99417 (15)0.90185 (15)0.88858 (12)0.0408 (5)
O21.09455 (15)0.99913 (16)0.96794 (12)0.0415 (5)
O31.20355 (19)0.77683 (19)0.89687 (15)0.0648 (7)
O40.78752 (16)0.88449 (16)0.79238 (13)0.0477 (6)
O50.83297 (17)1.02339 (17)0.84285 (14)0.0539 (6)
O60.80359 (19)1.00540 (19)0.71402 (15)0.0617 (7)
O70.80680 (17)0.70496 (17)1.02473 (14)0.0513 (6)
O80.8016 (2)0.83975 (18)1.08626 (14)0.0616 (7)
O90.8312 (2)0.7069 (2)1.15385 (16)0.0747 (8)
C11.0698 (2)0.9493 (2)0.90545 (18)0.0324 (7)
C21.1388 (2)0.9516 (2)0.84616 (19)0.0445 (8)
H2A1.12601.00970.81380.053*
H2B1.20410.95650.87570.053*
C31.1680 (3)0.7818 (3)0.8261 (2)0.0476 (9)
C41.1634 (3)0.6951 (3)0.7714 (2)0.0578 (10)
H4A1.20420.70600.73260.087*
H4B1.09810.68580.74450.087*
H4C1.18470.63820.80220.087*
C51.0850 (3)0.8778 (2)0.7122 (2)0.0453 (8)
C61.1368 (3)0.9001 (3)0.6535 (2)0.0712 (12)
H61.20290.91090.66640.085*
C71.0902 (4)0.9063 (4)0.5747 (3)0.0892 (16)
H71.12540.91970.53450.107*
C80.9928 (4)0.8930 (3)0.5559 (3)0.0789 (14)
H80.96180.89670.50300.095*
C90.9415 (3)0.8743 (3)0.6144 (3)0.0702 (12)
H90.87490.86710.60160.084*
C100.9867 (3)0.8656 (3)0.6927 (2)0.0560 (10)
H100.95100.85160.73240.067*
C110.8644 (2)0.6758 (2)0.80770 (19)0.0415 (8)
H110.81330.71130.77960.050*
C120.8938 (3)0.5933 (3)0.7716 (2)0.0478 (9)
H120.86340.57480.72080.057*
C130.9677 (3)0.5402 (3)0.8120 (2)0.0524 (10)
H130.98770.48400.78940.063*
C141.0140 (2)0.5703 (2)0.8879 (2)0.0427 (8)
C150.9805 (2)0.6557 (2)0.91969 (18)0.0345 (7)
C161.0281 (2)0.6891 (2)0.99698 (18)0.0346 (7)
C171.1050 (2)0.6354 (2)1.0390 (2)0.0451 (8)
C181.1482 (3)0.6695 (3)1.1146 (2)0.0540 (10)
H181.19900.63531.14460.065*
C191.1157 (3)0.7525 (3)1.1438 (2)0.0579 (10)
H191.14350.77541.19410.069*
C201.0401 (2)0.8028 (3)1.0977 (2)0.0481 (9)
H201.01970.86061.11780.058*
C211.0924 (3)0.5175 (3)0.9327 (2)0.0571 (10)
H211.11380.46100.91140.069*
C221.1358 (3)0.5483 (3)1.0052 (2)0.0554 (10)
H221.18640.51241.03370.067*
C230.6453 (2)0.7039 (2)0.87754 (19)0.0437 (8)
H230.69780.66190.88600.052*
C240.5551 (3)0.6658 (3)0.8443 (2)0.0543 (10)
H240.54810.60020.83140.065*
C250.4776 (3)0.7264 (3)0.8312 (2)0.0547 (10)
H250.41730.70270.80810.066*
C260.4886 (2)0.8241 (3)0.85246 (19)0.0434 (8)
C270.5820 (2)0.8562 (2)0.88643 (17)0.0351 (7)
C280.5960 (2)0.9564 (2)0.91083 (17)0.0355 (7)
C290.5157 (2)1.0197 (2)0.90190 (18)0.0410 (8)
C300.5319 (3)1.1161 (3)0.9279 (2)0.0493 (9)
H300.48091.15970.92350.059*
C310.6228 (3)1.1449 (3)0.9596 (2)0.0520 (10)
H310.63431.20800.97840.062*
C320.6986 (3)1.0792 (2)0.96363 (19)0.0465 (9)
H320.76081.10110.98280.056*
C330.4103 (2)0.8913 (3)0.8426 (2)0.0529 (10)
H330.34920.87030.81900.063*
C340.4227 (2)0.9842 (3)0.8666 (2)0.0512 (9)
H340.37001.02600.86020.061*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
La10.02833 (10)0.02659 (10)0.03019 (10)0.00055 (9)−0.00011 (7)−0.00327 (8)
N10.0487 (17)0.0416 (16)0.0405 (16)−0.0021 (14)0.0130 (13)−0.0099 (14)
N20.0389 (15)0.0313 (14)0.0356 (15)−0.0021 (12)0.0007 (12)−0.0046 (12)
N30.0357 (15)0.0316 (14)0.0403 (16)0.0000 (12)−0.0008 (12)−0.0019 (12)
N40.0377 (16)0.0355 (15)0.0399 (16)−0.0008 (13)0.0050 (12)0.0019 (12)
N50.0376 (16)0.0340 (15)0.0389 (16)0.0039 (12)0.0010 (12)0.0000 (12)
N60.0374 (16)0.0448 (18)0.0440 (18)0.0005 (14)0.0011 (13)0.0050 (15)
N70.0520 (19)0.052 (2)0.045 (2)−0.0089 (16)0.0103 (15)0.0023 (16)
O10.0377 (13)0.0455 (13)0.0386 (13)−0.0086 (11)0.0051 (10)−0.0102 (10)
O20.0406 (13)0.0418 (13)0.0416 (13)−0.0028 (11)0.0061 (10)−0.0147 (11)
O30.0758 (19)0.0630 (18)0.0515 (17)−0.0085 (15)−0.0001 (14)−0.0028 (14)
O40.0558 (15)0.0388 (13)0.0436 (14)−0.0127 (12)−0.0044 (11)0.0069 (11)
O50.0643 (17)0.0401 (14)0.0546 (16)−0.0048 (12)0.0028 (13)−0.0074 (12)
O60.0721 (18)0.0614 (17)0.0509 (16)0.0021 (14)0.0088 (13)0.0221 (14)
O70.0567 (16)0.0445 (14)0.0503 (15)−0.0004 (12)0.0025 (12)−0.0050 (12)
O80.094 (2)0.0383 (15)0.0581 (17)0.0041 (14)0.0289 (14)0.0002 (12)
O90.096 (2)0.077 (2)0.0511 (17)−0.0066 (17)0.0107 (15)0.0189 (15)
C10.0351 (18)0.0268 (16)0.0341 (18)0.0027 (14)0.0024 (14)−0.0043 (14)
C20.049 (2)0.041 (2)0.046 (2)−0.0068 (17)0.0148 (16)−0.0127 (16)
C30.045 (2)0.050 (2)0.052 (2)−0.0102 (18)0.0189 (18)−0.0066 (19)
C40.074 (3)0.042 (2)0.060 (2)−0.006 (2)0.020 (2)−0.0070 (19)
C50.054 (2)0.0401 (19)0.045 (2)0.0013 (18)0.0157 (17)−0.0090 (17)
C60.065 (3)0.093 (3)0.060 (3)0.005 (2)0.025 (2)0.008 (2)
C70.111 (4)0.106 (4)0.057 (3)0.022 (3)0.033 (3)0.019 (3)
C80.110 (4)0.071 (3)0.051 (3)0.022 (3)0.002 (3)−0.003 (2)
C90.074 (3)0.064 (3)0.066 (3)0.005 (2)−0.005 (2)−0.017 (2)
C100.062 (3)0.053 (2)0.053 (2)−0.006 (2)0.0125 (19)−0.0110 (19)
C110.042 (2)0.043 (2)0.038 (2)−0.0083 (16)0.0018 (15)−0.0070 (16)
C120.057 (2)0.046 (2)0.043 (2)−0.0117 (18)0.0143 (18)−0.0166 (17)
C130.071 (3)0.035 (2)0.059 (2)−0.0058 (19)0.033 (2)−0.0110 (18)
C140.051 (2)0.0297 (18)0.051 (2)0.0005 (16)0.0187 (17)0.0004 (16)
C150.0376 (18)0.0296 (17)0.0377 (18)−0.0029 (14)0.0105 (14)0.0017 (14)
C160.0351 (18)0.0300 (17)0.0390 (19)−0.0004 (14)0.0072 (14)0.0041 (14)
C170.0396 (19)0.043 (2)0.053 (2)0.0018 (17)0.0096 (16)0.0114 (18)
C180.045 (2)0.055 (2)0.057 (2)0.0069 (19)−0.0048 (18)0.016 (2)
C190.056 (2)0.063 (3)0.047 (2)0.002 (2)−0.0134 (19)0.0025 (19)
C200.050 (2)0.044 (2)0.044 (2)0.0024 (17)−0.0078 (17)−0.0058 (17)
C210.070 (3)0.035 (2)0.072 (3)0.0145 (19)0.029 (2)0.0054 (19)
C220.055 (2)0.044 (2)0.069 (3)0.0198 (19)0.015 (2)0.017 (2)
C230.041 (2)0.0371 (19)0.053 (2)−0.0028 (16)0.0078 (16)−0.0018 (17)
C240.055 (2)0.044 (2)0.063 (3)−0.0121 (19)0.0084 (19)−0.0058 (19)
C250.042 (2)0.059 (2)0.060 (2)−0.0133 (19)0.0020 (18)−0.002 (2)
C260.0361 (19)0.050 (2)0.044 (2)−0.0025 (17)0.0047 (15)0.0067 (17)
C270.0309 (17)0.0405 (19)0.0336 (17)0.0022 (15)0.0051 (13)0.0067 (14)
C280.0360 (18)0.0400 (19)0.0304 (17)0.0019 (15)0.0052 (14)0.0054 (14)
C290.040 (2)0.047 (2)0.0370 (19)0.0089 (17)0.0114 (15)0.0121 (16)
C300.053 (2)0.049 (2)0.046 (2)0.0220 (19)0.0081 (17)0.0064 (18)
C310.067 (3)0.040 (2)0.045 (2)0.0146 (19)−0.0013 (18)−0.0008 (16)
C320.050 (2)0.041 (2)0.044 (2)0.0034 (17)−0.0029 (17)−0.0035 (17)
C330.0310 (19)0.066 (3)0.061 (2)−0.0021 (18)0.0061 (16)0.011 (2)
C340.035 (2)0.061 (3)0.058 (2)0.0111 (19)0.0106 (17)0.019 (2)
Geometric parameters (Å, °) top
La1—O2i2.376 (2)C8—H80.9300
La1—O12.492 (2)C9—C101.376 (5)
La1—O42.593 (2)C9—H90.9300
La1—O82.610 (2)C10—H100.9300
La1—N32.680 (2)C11—C121.387 (5)
La1—N22.709 (2)C11—H110.9300
La1—O52.715 (2)C12—C131.356 (5)
La1—N52.740 (2)C12—H120.9300
La1—O72.754 (2)C13—C141.402 (5)
La1—N42.788 (3)C13—H130.9300
N1—C31.363 (4)C14—C151.408 (4)
N1—C51.433 (4)C14—C211.425 (5)
N1—C21.455 (4)C15—C161.441 (4)
N2—C111.327 (4)C16—C171.400 (4)
N2—C151.362 (4)C17—C181.403 (5)
N3—C201.321 (4)C17—C221.429 (5)
N3—C161.369 (4)C18—C191.357 (5)
N4—C231.325 (4)C18—H180.9300
N4—C271.364 (4)C19—C201.391 (5)
N5—C321.330 (4)C19—H190.9300
N5—C281.357 (4)C20—H200.9300
N6—O61.224 (3)C21—C221.345 (5)
N6—O51.252 (3)C21—H210.9300
N6—O41.268 (3)C22—H220.9300
N7—O91.229 (3)C23—C241.400 (4)
N7—O81.248 (4)C23—H230.9300
N7—O71.253 (3)C24—C251.361 (5)
O1—C11.239 (3)C24—H240.9300
O2—C11.261 (3)C25—C261.393 (5)
O2—La1i2.376 (2)C25—H250.9300
O3—C31.221 (4)C26—C271.411 (4)
C1—C21.518 (4)C26—C331.427 (5)
C2—H2A0.9700C27—C281.444 (4)
C2—H2B0.9700C28—C291.414 (4)
C3—C41.507 (5)C29—C301.403 (5)
C4—H4A0.9600C29—C341.428 (5)
C4—H4B0.9600C30—C311.358 (5)
C4—H4C0.9600C30—H300.9300
C5—C61.370 (5)C31—C321.392 (5)
C5—C101.376 (5)C31—H310.9300
C6—C71.387 (6)C32—H320.9300
C6—H60.9300C33—C341.344 (5)
C7—C81.365 (6)C33—H330.9300
C7—H70.9300C34—H340.9300
C8—C91.353 (6)
O2i—La1—O183.13 (7)C6—C5—C10119.7 (4)
O2i—La1—O4125.60 (7)C6—C5—N1119.8 (3)
O1—La1—O474.74 (7)C10—C5—N1120.5 (3)
O2i—La1—O870.80 (8)C5—C6—C7119.6 (4)
O1—La1—O8137.26 (8)C5—C6—H6120.2
O4—La1—O8147.97 (8)C7—C6—H6120.2
O2i—La1—N384.08 (7)C8—C7—C6120.2 (4)
O1—La1—N369.20 (7)C8—C7—H7119.9
O4—La1—N3129.44 (8)C6—C7—H7119.9
O8—La1—N374.80 (8)C9—C8—C7119.9 (4)
O2i—La1—N2141.31 (7)C9—C8—H8120.0
O1—La1—N269.05 (7)C7—C8—H8120.0
O4—La1—N273.23 (7)C8—C9—C10120.7 (4)
O8—La1—N2112.44 (8)C8—C9—H9119.6
N3—La1—N261.51 (7)C10—C9—H9119.6
O2i—La1—O577.98 (7)C5—C10—C9119.8 (4)
O1—La1—O565.36 (7)C5—C10—H10120.1
O4—La1—O547.63 (7)C9—C10—H10120.1
O8—La1—O5135.76 (8)N2—C11—C12124.2 (3)
N3—La1—O5132.60 (8)N2—C11—H11117.9
N2—La1—O5111.57 (7)C12—C11—H11117.9
O2i—La1—N577.10 (7)C13—C12—C11118.6 (3)
O1—La1—N5129.03 (7)C13—C12—H12120.7
O4—La1—N579.69 (7)C11—C12—H12120.7
O8—La1—N578.07 (8)C12—C13—C14119.9 (3)
N3—La1—N5150.86 (8)C12—C13—H13120.1
N2—La1—N5141.46 (7)C14—C13—H13120.1
O5—La1—N564.76 (7)C13—C14—C15117.8 (3)
O2i—La1—O7113.62 (7)C13—C14—C21122.1 (3)
O1—La1—O7125.74 (7)C15—C14—C21120.1 (3)
O4—La1—O7119.74 (7)N2—C15—C14122.0 (3)
O8—La1—O746.86 (7)N2—C15—C16119.2 (3)
N3—La1—O762.44 (7)C14—C15—C16118.8 (3)
N2—La1—O767.34 (7)N3—C16—C17122.2 (3)
O5—La1—O7163.54 (7)N3—C16—C15118.4 (3)
N5—La1—O7105.22 (7)C17—C16—C15119.4 (3)
O2i—La1—N4132.04 (7)C16—C17—C18117.6 (3)
O1—La1—N4139.19 (7)C16—C17—C22120.0 (3)
O4—La1—N467.69 (7)C18—C17—C22122.3 (3)
O8—La1—N481.15 (8)C19—C18—C17119.8 (3)
N3—La1—N4125.42 (8)C19—C18—H18120.1
N2—La1—N485.05 (8)C17—C18—H18120.1
O5—La1—N498.33 (7)C18—C19—C20119.2 (3)
N5—La1—N459.17 (8)C18—C19—H19120.4
O7—La1—N465.28 (7)C20—C19—H19120.4
C3—N1—C5123.5 (3)N3—C20—C19123.4 (3)
C3—N1—C2117.3 (3)N3—C20—H20118.3
C5—N1—C2119.0 (3)C19—C20—H20118.3
C11—N2—C15117.4 (3)C22—C21—C14120.9 (3)
C11—N2—La1122.7 (2)C22—C21—H21119.6
C15—N2—La1119.86 (18)C14—C21—H21119.6
C20—N3—C16117.8 (3)C21—C22—C17120.7 (3)
C20—N3—La1121.1 (2)C21—C22—H22119.6
C16—N3—La1121.06 (19)C17—C22—H22119.6
C23—N4—C27117.0 (3)N4—C23—C24123.8 (3)
C23—N4—La1121.8 (2)N4—C23—H23118.1
C27—N4—La1120.83 (19)C24—C23—H23118.1
C32—N5—C28117.8 (3)C25—C24—C23118.8 (3)
C32—N5—La1119.2 (2)C25—C24—H24120.6
C28—N5—La1122.8 (2)C23—C24—H24120.6
O6—N6—O5122.4 (3)C24—C25—C26120.0 (3)
O6—N6—O4120.8 (3)C24—C25—H25120.0
O5—N6—O4116.8 (3)C26—C25—H25120.0
O9—N7—O8121.4 (3)C25—C26—C27117.5 (3)
O9—N7—O7121.1 (3)C25—C26—C33123.1 (3)
O8—N7—O7117.4 (3)C27—C26—C33119.4 (3)
C1—O1—La1138.33 (19)N4—C27—C26122.8 (3)
C1—O2—La1i161.3 (2)N4—C27—C28118.0 (3)
N6—O4—La1100.05 (18)C26—C27—C28119.2 (3)
N6—O5—La194.59 (18)N5—C28—C29122.2 (3)
N7—O7—La192.03 (18)N5—C28—C27118.4 (3)
N7—O8—La199.1 (2)C29—C28—C27119.4 (3)
O1—C1—O2125.5 (3)C30—C29—C28117.7 (3)
O1—C1—C2118.8 (3)C30—C29—C34122.8 (3)
O2—C1—C2115.7 (3)C28—C29—C34119.5 (3)
N1—C2—C1115.0 (3)C31—C30—C29119.4 (3)
N1—C2—H2A108.5C31—C30—H30120.3
C1—C2—H2A108.5C29—C30—H30120.3
N1—C2—H2B108.5C30—C31—C32119.4 (3)
C1—C2—H2B108.5C30—C31—H31120.3
H2A—C2—H2B107.5C32—C31—H31120.3
O3—C3—N1120.5 (3)N5—C32—C31123.4 (3)
O3—C3—C4121.9 (4)N5—C32—H32118.3
N1—C3—C4117.5 (3)C31—C32—H32118.3
C3—C4—H4A109.5C34—C33—C26121.7 (3)
C3—C4—H4B109.5C34—C33—H33119.2
H4A—C4—H4B109.5C26—C33—H33119.2
C3—C4—H4C109.5C33—C34—C29120.9 (3)
H4A—C4—H4C109.5C33—C34—H34119.6
H4B—C4—H4C109.5C29—C34—H34119.6
O2i—La1—N2—C11−147.4 (2)N5—La1—O7—N7−68.74 (19)
O1—La1—N2—C11−100.4 (2)N4—La1—O7—N7−113.51 (19)
O4—La1—N2—C11−20.7 (2)O9—N7—O8—La1154.8 (3)
O8—La1—N2—C11125.7 (2)O7—N7—O8—La1−22.5 (3)
N3—La1—N2—C11−177.4 (3)O2i—La1—O8—N7−143.0 (2)
O5—La1—N2—C11−49.6 (2)O1—La1—O8—N7−87.3 (2)
N5—La1—N2—C1126.6 (3)O4—La1—O8—N789.7 (2)
O7—La1—N2—C11112.7 (2)N3—La1—O8—N7−54.1 (2)
N4—La1—N2—C1147.4 (2)N2—La1—O8—N7−4.4 (2)
O2i—La1—N2—C1530.4 (3)O5—La1—O8—N7169.36 (18)
O1—La1—N2—C1577.3 (2)N5—La1—O8—N7136.7 (2)
O4—La1—N2—C15157.0 (2)O7—La1—O8—N712.21 (18)
O8—La1—N2—C15−56.6 (2)N4—La1—O8—N776.5 (2)
N3—La1—N2—C150.3 (2)La1—O1—C1—O23.0 (5)
O5—La1—N2—C15128.1 (2)La1—O1—C1—C2−175.1 (2)
N5—La1—N2—C15−155.73 (19)La1i—O2—C1—O1−135.8 (5)
O7—La1—N2—C15−69.6 (2)La1i—O2—C1—C242.3 (7)
N4—La1—N2—C15−134.9 (2)C3—N1—C2—C1−71.2 (4)
O2i—La1—N3—C2018.8 (2)C5—N1—C2—C1103.4 (3)
O1—La1—N3—C20103.7 (3)O1—C1—C2—N1−26.0 (4)
O4—La1—N3—C20151.1 (2)O2—C1—C2—N1155.8 (3)
O8—La1—N3—C20−52.8 (2)C5—N1—C3—O3−175.7 (3)
N2—La1—N3—C20−179.5 (3)C2—N1—C3—O3−1.3 (5)
O5—La1—N3—C2086.5 (3)C5—N1—C3—C46.1 (5)
N5—La1—N3—C20−30.9 (3)C2—N1—C3—C4−179.5 (3)
O7—La1—N3—C20−101.7 (3)C3—N1—C5—C6−91.5 (4)
N4—La1—N3—C20−119.9 (2)C2—N1—C5—C694.2 (4)
O2i—La1—N3—C16−162.5 (2)C3—N1—C5—C1088.9 (4)
O1—La1—N3—C16−77.6 (2)C2—N1—C5—C10−85.5 (4)
O4—La1—N3—C16−30.2 (3)C10—C5—C6—C7−2.5 (6)
O8—La1—N3—C16125.8 (2)N1—C5—C6—C7177.8 (4)
N2—La1—N3—C16−0.8 (2)C5—C6—C7—C81.8 (7)
O5—La1—N3—C16−94.8 (2)C6—C7—C8—C90.5 (7)
N5—La1—N3—C16147.8 (2)C7—C8—C9—C10−1.9 (7)
O7—La1—N3—C1677.0 (2)C6—C5—C10—C91.1 (6)
N4—La1—N3—C1658.7 (2)N1—C5—C10—C9−179.3 (3)
O2i—La1—N4—C23−151.3 (2)C8—C9—C10—C51.1 (6)
O1—La1—N4—C2365.8 (3)C15—N2—C11—C121.1 (5)
O4—La1—N4—C2390.2 (2)La1—N2—C11—C12178.9 (2)
O8—La1—N4—C23−97.3 (2)N2—C11—C12—C130.5 (5)
N3—La1—N4—C23−33.2 (3)C11—C12—C13—C14−1.3 (5)
N2—La1—N4—C2316.3 (2)C12—C13—C14—C150.4 (5)
O5—La1—N4—C23127.4 (2)C12—C13—C14—C21−179.6 (3)
N5—La1—N4—C23−178.7 (3)C11—N2—C15—C14−2.0 (4)
O7—La1—N4—C23−51.0 (2)La1—N2—C15—C14−179.9 (2)
O2i—La1—N4—C2735.3 (3)C11—N2—C15—C16178.1 (3)
O1—La1—N4—C27−107.6 (2)La1—N2—C15—C160.2 (4)
O4—La1—N4—C27−83.2 (2)C13—C14—C15—N21.3 (5)
O8—La1—N4—C2789.3 (2)C21—C14—C15—N2−178.7 (3)
N3—La1—N4—C27153.4 (2)C13—C14—C15—C16−178.8 (3)
N2—La1—N4—C27−157.1 (2)C21—C14—C15—C161.2 (5)
O5—La1—N4—C27−45.9 (2)C20—N3—C16—C170.1 (5)
N5—La1—N4—C278.0 (2)La1—N3—C16—C17−178.6 (2)
O7—La1—N4—C27135.6 (2)C20—N3—C16—C15−179.9 (3)
O2i—La1—N5—C3219.8 (2)La1—N3—C16—C151.3 (4)
O1—La1—N5—C32−50.2 (3)N2—C15—C16—N3−1.0 (4)
O4—La1—N5—C32−110.7 (2)C14—C15—C16—N3179.1 (3)
O8—La1—N5—C3292.5 (2)N2—C15—C16—C17178.9 (3)
N3—La1—N5—C3270.9 (3)C14—C15—C16—C17−1.0 (4)
N2—La1—N5—C32−156.3 (2)N3—C16—C17—C181.1 (5)
O5—La1—N5—C32−62.9 (2)C15—C16—C17—C18−178.8 (3)
O7—La1—N5—C32131.1 (2)N3—C16—C17—C22179.9 (3)
N4—La1—N5—C32179.2 (3)C15—C16—C17—C220.0 (5)
O2i—La1—N5—C28−166.6 (2)C16—C17—C18—C19−0.9 (5)
O1—La1—N5—C28123.5 (2)C22—C17—C18—C19−179.7 (4)
O4—La1—N5—C2862.9 (2)C17—C18—C19—C20−0.5 (6)
O8—La1—N5—C28−93.9 (2)C16—N3—C20—C19−1.6 (5)
N3—La1—N5—C28−115.5 (2)La1—N3—C20—C19177.1 (3)
N2—La1—N5—C2817.3 (3)C18—C19—C20—N31.8 (6)
O5—La1—N5—C28110.8 (2)C13—C14—C21—C22179.7 (3)
O7—La1—N5—C28−55.3 (2)C15—C14—C21—C22−0.4 (5)
N4—La1—N5—C28−7.1 (2)C14—C21—C22—C17−0.7 (6)
O2i—La1—O1—C111.0 (3)C16—C17—C22—C210.9 (5)
O4—La1—O1—C1140.9 (3)C18—C17—C22—C21179.7 (3)
O8—La1—O1—C1−40.8 (3)C27—N4—C23—C241.5 (5)
N3—La1—O1—C1−75.2 (3)La1—N4—C23—C24−172.2 (3)
N2—La1—O1—C1−141.6 (3)N4—C23—C24—C250.3 (5)
O5—La1—O1—C190.9 (3)C23—C24—C25—C26−1.4 (5)
N5—La1—O1—C178.2 (3)C24—C25—C26—C270.7 (5)
O7—La1—O1—C1−103.2 (3)C24—C25—C26—C33−178.2 (3)
N4—La1—O1—C1164.2 (3)C23—N4—C27—C26−2.2 (4)
O6—N6—O4—La1170.4 (2)La1—N4—C27—C26171.5 (2)
O5—N6—O4—La1−10.1 (3)C23—N4—C27—C28177.6 (3)
O2i—La1—O4—N64.9 (2)La1—N4—C27—C28−8.7 (4)
O1—La1—O4—N6−64.73 (18)C25—C26—C27—N41.1 (5)
O8—La1—O4—N6117.36 (19)C33—C26—C27—N4−179.9 (3)
N3—La1—O4—N6−110.21 (18)C25—C26—C27—C28−178.7 (3)
N2—La1—O4—N6−136.97 (19)C33—C26—C27—C280.3 (5)
O5—La1—O4—N65.63 (16)C32—N5—C28—C290.1 (4)
N5—La1—O4—N670.76 (18)La1—N5—C28—C29−173.6 (2)
O7—La1—O4—N6172.49 (17)C32—N5—C28—C27179.9 (3)
N4—La1—O4—N6131.5 (2)La1—N5—C28—C276.2 (4)
O6—N6—O5—La1−170.9 (3)N4—C27—C28—N51.8 (4)
O4—N6—O5—La19.6 (3)C26—C27—C28—N5−178.4 (3)
O2i—La1—O5—N6173.77 (19)N4—C27—C28—C29−178.4 (3)
O1—La1—O5—N685.88 (18)C26—C27—C28—C291.5 (4)
O4—La1—O5—N6−5.63 (16)N5—C28—C29—C30−1.6 (5)
O8—La1—O5—N6−140.71 (17)C27—C28—C29—C30178.6 (3)
N3—La1—O5—N6103.60 (18)N5—C28—C29—C34177.9 (3)
N2—La1—O5—N633.07 (19)C27—C28—C29—C34−2.0 (4)
N5—La1—O5—N6−104.96 (19)C28—C29—C30—C310.6 (5)
O7—La1—O5—N6−49.8 (3)C34—C29—C30—C31−178.8 (3)
N4—La1—O5—N6−54.87 (18)C29—C30—C31—C321.7 (5)
O9—N7—O7—La1−156.3 (3)C28—N5—C32—C312.5 (5)
O8—N7—O7—La121.0 (3)La1—N5—C32—C31176.4 (3)
O2i—La1—O7—N713.6 (2)C30—C31—C32—N5−3.4 (5)
O1—La1—O7—N7112.44 (18)C25—C26—C33—C34177.3 (4)
O4—La1—O7—N7−155.40 (17)C27—C26—C33—C34−1.6 (5)
O8—La1—O7—N7−12.01 (18)C26—C33—C34—C291.1 (5)
N3—La1—O7—N782.79 (19)C30—C29—C34—C33−179.9 (3)
N2—La1—O7—N7151.4 (2)C28—C29—C34—C330.7 (5)
O5—La1—O7—N7−119.1 (3)
Symmetry codes: (i) −x+2, −y+2, −z+2.
Table 1
Selected geometric parameters (°) top
O1—La1—O474.74 (7)
Acknowledgements top

We are grateful for financial support from the National Natural Science Foundation of China (grant No. 20771021) and Shandong Natural Science Foundation (grant No. Y2005B20).

references
References top

Bruker (1997). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.

Fu, A.-Y., Wang, D.-Q. & Shen, Q.-J. (2004a). Acta Cryst. E60, m1346–m1348.

Fu, A.-Y., Wang, D.-Q., Shen, Q.-J. & Zhang, C.-L. (2004b). Acta Cryst. E60, m1337–m1339.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.