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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): m163.
Published online 2010 January 16. doi:  10.1107/S1600536809055743
PMCID: PMC2979887

Bis(μ-2-methyl-8-oxidoquinolin-1-ium-κ2 O:O)bis­[(acetato-κ2 O,O′)(2-methyl-8-oxidoquinolin-1-ium-κO)bis­(nitrato-κ2 O,O′)lanthanum(III)]

Abstract

The N-heterocycles in the centrosymmetric title compound, [La2(C10H9NO)4(CH3COO)2(NO3)4], exist in the zwitterionic form. One heterocycle binds to a metal center whereas the other bridges two metal centers. Each La atom is chelated by an acetate and two nitrate groups and is surrounded by nine O atoms in a distorted tricapped trigonal-prismatic coordination environment. The N—H groups form intra­molecular N—H(...)O hydrogen bonds. One of the nitrate ions is disordered over two positions in a 0.80 (3):0.20 (3) occupancy ratio.

Related literature

For bis­(μ-2-methyl­quinolin-1-ium-8-olato)bis­[(2-methyl­quin­o­lin-1-ium-8-olato-)tris­(nitrato)lanthanum(III)], see: Faza­eli et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0m163-scheme1.jpg

Experimental

Crystal data

  • [La2(C10H9NO)4(C2H3O2)2(NO3)4]
  • M r = 1280.68
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0m163-efi1.jpg
  • a = 11.3686 (8) Å
  • b = 17.5807 (12) Å
  • c = 13.0265 (10) Å
  • β = 104.820 (1)°
  • V = 2517.0 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 1.76 mm−1
  • T = 295 K
  • 0.35 × 0.15 × 0.05 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.578, T max = 0.917
  • 15685 measured reflections
  • 5769 independent reflections
  • 4544 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.032
  • wR(F 2) = 0.112
  • S = 1.11
  • 5769 reflections
  • 358 parameters
  • 58 restraints
  • H atoms treated by a mixture of independent and constrained refinement
  • Δρmax = 0.84 e Å−3
  • Δρmin = −0.77 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809055743/bt5149sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809055743/bt5149Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Shahid Beheshti University and the University of Malaya for supporting this study.

supplementary crystallographic information

Experimental

2-Methyl-8-hydroxyquinoline (0.16 g, 1 mmol) and sodium acetate (0.08, 1 mmol) were added reacted with lanthanum nitrate hexahydrate (0.43 g, 1 mmol) in methanol (10 ml). The mixture was stirred two hours. Slow evaporation of the solution gave deep orange color crystals that are stable when heated up to 573 K.

Refinement

Carbon-bound H-atoms were placed in calculated positions (C–H 0.93–0.96 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

The nitrogen-bound H atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.86±0.01 Å; the displacement parameters of these H atoms were refined.

One of the nitrate ions is disordered over two positions; the occupancy of the major occupied site refined to 0.80 (3). The N–O distances as well as the O···O distances were restrained to be equal within 0.01 Å of each other. The four-atom unit was restrained to be planar. The isotropic displacement parameters of the primed atoms were set to the equivalent isotropic temperature factors of the unprimed ones, and the anisotropic temperature factors of these unprimed atoms were restrained to be nearly isotropic.

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound; ellipsoids are drawn at the 50% probability level and H atoms of arbitrary radius. The minor occupied site of the disorder nitrate ion is not shown.

Crystal data

[La2(C10H9NO)4(C2H3O2)2(NO3)4]F(000) = 1272
Mr = 1280.68Dx = 1.690 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 7894 reflections
a = 11.3686 (8) Åθ = 2.2–27.8°
b = 17.5807 (12) ŵ = 1.76 mm1
c = 13.0265 (10) ÅT = 295 K
β = 104.820 (1)°Block, orange
V = 2517.0 (3) Å30.35 × 0.15 × 0.05 mm
Z = 2

Data collection

Bruker SMART APEX diffractometer5769 independent reflections
Radiation source: fine-focus sealed tube4544 reflections with I > 2σ(I)
graphiteRint = 0.030
ω scansθmax = 27.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −14→12
Tmin = 0.578, Tmax = 0.917k = −17→22
15685 measured reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112H atoms treated by a mixture of independent and constrained refinement
S = 1.11w = 1/[σ2(Fo2) + (0.0493P)2 + 4.7409P] where P = (Fo2 + 2Fc2)/3
5769 reflections(Δ/σ)max = 0.001
358 parametersΔρmax = 0.84 e Å3
58 restraintsΔρmin = −0.76 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/UeqOcc. (<1)
La10.59038 (2)0.543193 (14)0.648779 (18)0.02973 (9)
O10.4836 (3)0.53330 (19)0.7782 (3)0.0433 (8)
O20.5705 (3)0.54741 (16)0.4544 (2)0.0298 (6)
O30.6618 (3)0.4169 (2)0.7427 (3)0.0490 (9)
O40.7505 (3)0.44741 (19)0.6178 (3)0.0466 (9)
O50.3958 (7)0.6311 (4)0.5777 (6)0.0566 (18)0.80 (3)
O5'0.420 (3)0.6466 (19)0.570 (2)0.057*0.20 (3)
O60.5573 (5)0.6913 (4)0.6548 (12)0.085 (3)0.80 (3)
O6'0.567 (2)0.677 (2)0.704 (3)0.085*0.20 (3)
O70.3882 (10)0.7522 (4)0.6030 (10)0.103 (3)0.80 (3)
O7'0.428 (4)0.7585 (17)0.638 (4)0.103*0.20 (3)
O80.7936 (4)0.6159 (2)0.6401 (3)0.0556 (10)
O90.7741 (4)0.5927 (3)0.7967 (3)0.0620 (11)
O100.9344 (4)0.6514 (3)0.7766 (4)0.0782 (14)
N10.5090 (4)0.4012 (2)0.8897 (3)0.0398 (9)
N20.7810 (3)0.4997 (2)0.4128 (3)0.0360 (9)
N30.4457 (7)0.6920 (3)0.6115 (6)0.0563 (18)0.80 (3)
N3'0.472 (3)0.6941 (14)0.638 (2)0.056*0.20 (3)
N40.8361 (4)0.6214 (3)0.7390 (4)0.0470 (10)
C10.4074 (4)0.5195 (3)0.8361 (3)0.0363 (10)
C20.3143 (5)0.5680 (3)0.8457 (4)0.0474 (12)
H2A0.30380.61400.80930.057*
C30.2355 (5)0.5488 (4)0.9092 (4)0.0597 (16)
H30.17340.58220.91290.072*
C40.2472 (6)0.4829 (4)0.9653 (5)0.0618 (16)
H40.19440.47211.00740.074*
C50.3394 (5)0.4310 (3)0.9597 (4)0.0494 (13)
C60.4183 (5)0.4505 (3)0.8952 (4)0.0384 (11)
C70.3617 (6)0.3623 (4)1.0154 (4)0.0602 (16)
H70.31240.34821.05930.072*
C80.4531 (7)0.3161 (3)1.0068 (4)0.0597 (17)
H80.46520.27031.04390.072*
C90.5307 (6)0.3360 (3)0.9425 (4)0.0503 (13)
C100.6331 (7)0.2879 (4)0.9293 (5)0.0681 (18)
H10A0.69720.31980.91800.102*
H10B0.60530.25490.86920.102*
H10C0.66320.25790.99200.102*
C110.6280 (4)0.5961 (3)0.4055 (3)0.0302 (9)
C120.5900 (4)0.6680 (3)0.3746 (4)0.0396 (11)
H120.52070.68720.39080.048*
C130.6541 (5)0.7138 (3)0.3183 (4)0.0509 (13)
H130.62590.76280.29940.061*
C140.7547 (5)0.6897 (3)0.2905 (4)0.0512 (13)
H140.79320.72080.25130.061*
C150.7998 (4)0.6162 (3)0.3222 (4)0.0410 (11)
C160.7377 (4)0.5703 (3)0.3809 (3)0.0326 (9)
C170.9041 (5)0.5839 (4)0.2988 (5)0.0527 (14)
H170.94780.61210.26070.063*
C180.9410 (5)0.5128 (4)0.3310 (5)0.0586 (16)
H181.00940.49270.31410.070*
C190.8779 (4)0.4684 (3)0.3897 (4)0.0443 (12)
C200.9120 (5)0.3891 (3)0.4264 (5)0.0587 (15)
H20A0.89420.38100.49370.088*
H20B0.99740.38160.43370.088*
H20C0.86640.35370.37540.088*
C210.7278 (4)0.3996 (3)0.6821 (4)0.0436 (11)
C220.7752 (6)0.3200 (4)0.6835 (6)0.074 (2)
H22A0.82540.30850.75290.110*
H22B0.82250.31550.63230.110*
H22C0.70820.28510.66590.110*
H10.552 (4)0.410 (3)0.845 (3)0.043 (14)*
H20.748 (4)0.472 (2)0.452 (3)0.042 (15)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
La10.03124 (15)0.03346 (15)0.02601 (13)−0.00429 (11)0.01007 (9)−0.00058 (10)
O10.055 (2)0.046 (2)0.0370 (17)−0.0002 (16)0.0253 (16)0.0023 (14)
O20.0299 (15)0.0332 (16)0.0284 (14)−0.0021 (12)0.0112 (12)0.0018 (12)
O30.053 (2)0.051 (2)0.047 (2)0.0087 (18)0.0209 (17)0.0113 (17)
O40.050 (2)0.041 (2)0.054 (2)0.0048 (16)0.0236 (17)0.0087 (16)
O50.052 (3)0.039 (3)0.076 (3)−0.006 (2)0.011 (3)−0.003 (3)
O60.073 (4)0.033 (3)0.127 (7)−0.005 (3)−0.013 (4)−0.011 (3)
O70.116 (6)0.073 (4)0.119 (6)0.053 (4)0.026 (5)−0.015 (4)
O80.061 (2)0.065 (3)0.044 (2)−0.026 (2)0.0209 (18)−0.0052 (18)
O90.055 (2)0.093 (3)0.0380 (19)−0.027 (2)0.0114 (17)0.002 (2)
O100.045 (2)0.105 (4)0.081 (3)−0.033 (2)0.010 (2)−0.011 (3)
N10.053 (3)0.039 (2)0.0288 (19)−0.0081 (19)0.0135 (18)−0.0017 (16)
N20.034 (2)0.045 (2)0.0330 (19)−0.0017 (18)0.0151 (16)−0.0014 (17)
N30.062 (4)0.055 (4)0.053 (4)0.019 (3)0.019 (3)−0.006 (3)
N40.039 (2)0.051 (3)0.050 (2)−0.011 (2)0.0106 (19)−0.008 (2)
C10.043 (3)0.041 (3)0.026 (2)−0.008 (2)0.0112 (19)−0.0061 (18)
C20.057 (3)0.052 (3)0.035 (2)0.001 (3)0.016 (2)−0.002 (2)
C30.043 (3)0.096 (5)0.043 (3)0.000 (3)0.017 (2)−0.010 (3)
C40.059 (4)0.089 (5)0.047 (3)−0.020 (3)0.030 (3)−0.006 (3)
C50.054 (3)0.065 (4)0.031 (2)−0.021 (3)0.014 (2)−0.006 (2)
C60.048 (3)0.042 (3)0.026 (2)−0.013 (2)0.0116 (19)−0.0040 (19)
C70.083 (4)0.064 (4)0.042 (3)−0.025 (3)0.032 (3)−0.002 (3)
C80.104 (5)0.035 (3)0.044 (3)−0.033 (3)0.026 (3)−0.002 (2)
C90.077 (4)0.039 (3)0.035 (2)−0.009 (3)0.014 (2)−0.002 (2)
C100.101 (5)0.054 (4)0.050 (3)0.007 (4)0.021 (3)0.008 (3)
C110.027 (2)0.039 (2)0.0233 (18)−0.0047 (18)0.0037 (16)0.0001 (17)
C120.038 (3)0.038 (3)0.044 (3)0.000 (2)0.012 (2)0.002 (2)
C130.052 (3)0.047 (3)0.052 (3)−0.011 (3)0.010 (2)0.003 (2)
C140.060 (3)0.053 (3)0.043 (3)−0.014 (3)0.017 (2)0.013 (2)
C150.032 (2)0.061 (3)0.030 (2)−0.014 (2)0.0090 (18)−0.006 (2)
C160.029 (2)0.043 (3)0.0243 (19)−0.0067 (19)0.0034 (16)−0.0024 (18)
C170.045 (3)0.065 (4)0.054 (3)−0.019 (3)0.023 (2)−0.007 (3)
C180.039 (3)0.079 (4)0.069 (4)−0.007 (3)0.035 (3)−0.020 (3)
C190.033 (2)0.057 (3)0.042 (3)0.001 (2)0.008 (2)−0.013 (2)
C200.050 (3)0.064 (4)0.062 (4)0.012 (3)0.013 (3)−0.010 (3)
C210.035 (3)0.045 (3)0.049 (3)0.004 (2)0.008 (2)0.011 (2)
C220.075 (4)0.049 (4)0.105 (6)0.025 (3)0.038 (4)0.019 (4)

Geometric parameters (Å, °)

La1—O12.322 (3)C3—C41.358 (9)
La1—O22.485 (3)C3—H30.9300
La1—O6'2.49 (3)C4—C51.405 (9)
La1—O2i2.536 (3)C4—H40.9300
La1—O32.564 (4)C5—C71.399 (8)
La1—O42.586 (3)C5—C61.418 (7)
La1—O92.603 (4)C7—C81.346 (9)
La1—O5'2.66 (3)C7—H70.9300
La1—O62.635 (6)C8—C91.408 (8)
La1—O52.663 (7)C8—H80.9300
La1—O82.668 (4)C9—C101.484 (9)
La1—C212.942 (5)C10—H10A0.9600
O1—C11.309 (5)C10—H10B0.9600
O2—C111.334 (5)C10—H10C0.9600
O2—La1i2.536 (3)C11—C121.363 (6)
O3—C211.257 (6)C11—C161.438 (6)
O4—C211.260 (6)C12—C131.410 (7)
O5—N31.239 (6)C12—H120.9300
O5'—N3'1.241 (7)C13—C141.353 (8)
O6—N31.250 (6)C13—H130.9300
O6'—N3'1.241 (7)C14—C151.412 (8)
O7—N31.233 (5)C14—H140.9300
O7'—N3'1.240 (7)C15—C171.416 (7)
O8—N41.258 (6)C15—C161.417 (6)
O9—N41.260 (5)C17—C181.351 (9)
O10—N41.219 (5)C17—H170.9300
N1—C91.327 (7)C18—C191.410 (8)
N1—C61.362 (7)C18—H180.9300
N1—H10.859 (10)C19—C201.492 (8)
N2—C191.333 (6)C20—H20A0.9600
N2—C161.362 (6)C20—H20B0.9600
N2—H20.861 (10)C20—H20C0.9600
C1—C21.389 (7)C21—C221.498 (8)
C1—C61.426 (7)C22—H22A0.9600
C2—C31.408 (8)C22—H22B0.9600
C2—H2A0.9300C22—H22C0.9600
O1—La1—O2144.47 (11)O5'—N3'—O6'119.9 (7)
O1—La1—O6'75.4 (9)O7'—N3'—La1176.0 (13)
O2—La1—O6'106.1 (9)O5'—N3'—La163.9 (12)
O1—La1—O2i84.12 (11)O6'—N3'—La156.0 (12)
O2—La1—O2i67.27 (11)O10—N4—O8121.1 (5)
O6'—La1—O2i129.1 (6)O10—N4—O9121.9 (5)
O1—La1—O375.49 (11)O8—N4—O9117.0 (4)
O2—La1—O3116.55 (11)O10—N4—La1178.6 (4)
O6'—La1—O3136.3 (9)O8—N4—La160.0 (2)
O2i—La1—O378.84 (11)O9—N4—La157.0 (2)
O1—La1—O4125.74 (11)O1—C1—C2124.7 (5)
O2—La1—O475.19 (11)O1—C1—C6119.3 (4)
O6'—La1—O4142.2 (6)C2—C1—C6115.9 (4)
O2i—La1—O487.10 (11)C1—C2—C3121.3 (5)
O3—La1—O450.30 (11)C1—C2—H2A119.4
O1—La1—O987.53 (12)C3—C2—H2A119.4
O2—La1—O9126.22 (10)C4—C3—C2122.1 (6)
O6'—La1—O966.1 (6)C4—C3—H3118.9
O2i—La1—O9159.37 (12)C2—C3—H3118.9
O3—La1—O980.82 (13)C3—C4—C5119.9 (5)
O4—La1—O982.54 (14)C3—C4—H4120.1
O1—La1—O5'82.3 (8)C5—C4—H4120.1
O2—La1—O5'73.8 (6)C7—C5—C4124.9 (5)
O6'—La1—O5'49.1 (5)C7—C5—C6117.3 (6)
O2i—La1—O5'82.6 (7)C4—C5—C6117.9 (5)
O3—La1—O5'152.3 (8)N1—C6—C5118.7 (5)
O4—La1—O5'148.9 (7)N1—C6—C1118.4 (4)
O9—La1—O5'115.0 (6)C5—C6—C1123.0 (5)
O1—La1—O687.0 (3)C8—C7—C5121.2 (5)
O2—La1—O691.4 (3)C8—C7—H7119.4
O6'—La1—O614.7 (7)C5—C7—H7119.4
O2i—La1—O6123.18 (19)C7—C8—C9121.0 (5)
O3—La1—O6150.6 (3)C7—C8—H8119.5
O4—La1—O6139.4 (2)C9—C8—H8119.5
O9—La1—O675.0 (2)N1—C9—C8117.4 (6)
O5'—La1—O640.6 (6)N1—C9—C10118.7 (5)
O1—La1—O575.8 (2)C8—C9—C10123.9 (5)
O2—La1—O577.14 (18)C9—C10—H10A109.5
O6'—La1—O554.1 (6)C9—C10—H10B109.5
O2i—La1—O575.98 (17)H10A—C10—H10B109.5
O3—La1—O5143.3 (2)C9—C10—H10C109.5
O4—La1—O5151.49 (17)H10A—C10—H10C109.5
O9—La1—O5120.07 (17)H10B—C10—H10C109.5
O5'—La1—O59.0 (7)O2—C11—C12125.4 (4)
O6—La1—O547.51 (16)O2—C11—C16117.6 (4)
O1—La1—O8133.29 (12)C12—C11—C16117.0 (4)
O2—La1—O878.27 (10)C11—C12—C13121.1 (5)
O6'—La1—O873.6 (7)C11—C12—H12119.5
O2i—La1—O8142.52 (10)C13—C12—H12119.5
O3—La1—O8105.23 (13)C14—C13—C12123.0 (5)
O4—La1—O869.72 (12)C14—C13—H13118.5
O9—La1—O848.04 (11)C12—C13—H13118.5
O5'—La1—O8102.1 (8)C13—C14—C15118.5 (5)
O6—La1—O870.12 (18)C13—C14—H14120.8
O5—La1—O8111.0 (2)C15—C14—H14120.8
O1—La1—C21100.66 (13)C14—C15—C17124.4 (5)
O2—La1—C2194.73 (12)C14—C15—C16119.0 (5)
O6'—La1—C21149.1 (7)C17—C15—C16116.6 (5)
O2i—La1—C2179.82 (12)N2—C16—C15119.6 (4)
O3—La1—C2125.22 (12)N2—C16—C11119.1 (4)
O4—La1—C2125.30 (12)C15—C16—C11121.4 (4)
O9—La1—C2183.26 (15)C18—C17—C15121.0 (5)
O5'—La1—C21161.7 (6)C18—C17—H17119.5
O6—La1—C21156.65 (18)C15—C17—H17119.5
O5—La1—C21155.77 (18)C17—C18—C19121.3 (5)
O8—La1—C2189.09 (13)C17—C18—H18119.4
C1—O1—La1168.0 (3)C19—C18—H18119.4
C11—O2—La1125.3 (2)N2—C19—C18117.3 (5)
C11—O2—La1i121.7 (2)N2—C19—C20118.3 (5)
La1—O2—La1i112.73 (10)C18—C19—C20124.3 (5)
C21—O3—La194.4 (3)C19—C20—H20A109.5
C21—O4—La193.3 (3)C19—C20—H20B109.5
N3—O5—La196.5 (4)H20A—C20—H20B109.5
N3'—O5'—La191.4 (12)C19—C20—H20C109.5
N3—O6—La197.6 (4)H20A—C20—H20C109.5
N3'—O6'—La199.6 (13)H20B—C20—H20C109.5
N4—O8—La195.9 (3)O3—C21—O4120.8 (5)
N4—O9—La199.0 (3)O3—C21—C22119.3 (5)
C9—N1—C6124.4 (4)O4—C21—C22119.8 (5)
C9—N1—H1116 (4)O3—C21—La160.3 (3)
C6—N1—H1119 (4)O4—C21—La161.4 (3)
C19—N2—C16124.2 (4)C22—C21—La1168.3 (4)
C19—N2—H2114 (3)C21—C22—H22A109.5
C16—N2—H2122 (3)C21—C22—H22B109.5
O7—N3—O5121.7 (5)H22A—C22—H22B109.5
O7—N3—O6120.1 (5)C21—C22—H22C109.5
O5—N3—O6118.1 (5)H22A—C22—H22C109.5
O7'—N3'—O5'120.2 (7)H22B—C22—H22C109.5
O7'—N3'—O6'120.0 (7)
O2—La1—O1—C129.7 (17)La1—O6—N3—O5−4.4 (5)
O6'—La1—O1—C1127.1 (18)La1—O5'—N3'—O7'−179.9 (17)
O2i—La1—O1—C1−5.9 (16)La1—O5'—N3'—O6'0.1 (17)
O3—La1—O1—C1−85.8 (16)La1—O6'—N3'—O7'179.9 (19)
O4—La1—O1—C1−88.0 (16)La1—O6'—N3'—O5'−0.1 (19)
O9—La1—O1—C1−167.0 (16)O1—La1—N3'—O5'−98.4 (18)
O5'—La1—O1—C177.4 (17)O2—La1—N3'—O5'48.0 (18)
O6—La1—O1—C1117.9 (16)O6'—La1—N3'—O5'179.9 (18)
O5—La1—O1—C171.1 (16)O2i—La1—N3'—O5'−18.3 (19)
O8—La1—O1—C1176.7 (16)O3—La1—N3'—O5'−115 (2)
C21—La1—O1—C1−84.3 (16)O4—La1—N3'—O5'101.2 (18)
O1—La1—O2—C11135.0 (3)O9—La1—N3'—O5'174.2 (18)
O6'—La1—O2—C1147.8 (7)O6—La1—N3'—O5'142 (2)
O2i—La1—O2—C11174.0 (4)O5—La1—N3'—O5'−15.6 (18)
O3—La1—O2—C11−122.4 (3)O8—La1—N3'—O5'126.3 (18)
O4—La1—O2—C11−92.9 (3)O1—La1—N3'—O6'81.7 (19)
O9—La1—O2—C11−24.1 (4)O4—La1—N3'—O6'−78.7 (19)
O5'—La1—O2—C1185.4 (8)O5'—La1—N3'—O6'−179.9 (18)
O6—La1—O2—C1148.3 (3)O5—La1—N3'—O6'164.5 (19)
O5—La1—O2—C1194.0 (4)La1—O8—N4—O10179.0 (5)
O8—La1—O2—C11−21.1 (3)La1—O8—N4—O90.9 (5)
C21—La1—O2—C11−109.2 (3)La1—O9—N4—O10−179.0 (5)
O1—La1—O2—La1i−38.9 (2)La1—O9—N4—O8−1.0 (5)
O6'—La1—O2—La1i−126.2 (7)O1—La1—N4—O8−163.4 (3)
O2i—La1—O2—La1i0.0O2—La1—N4—O82.7 (3)
O3—La1—O2—La1i63.64 (15)O6'—La1—N4—O8−99.8 (11)
O4—La1—O2—La1i93.10 (13)O2i—La1—N4—O856.4 (5)
O9—La1—O2—La1i161.98 (14)O3—La1—N4—O8120.8 (3)
O5'—La1—O2—La1i−88.6 (8)O4—La1—N4—O873.5 (3)
O6—La1—O2—La1i−125.68 (16)O9—La1—N4—O8179.0 (5)
O5—La1—O2—La1i−80.0 (2)O5'—La1—N4—O8−74.3 (8)
O8—La1—O2—La1i164.96 (15)O6—La1—N4—O8−84.4 (5)
C21—La1—O2—La1i76.88 (14)O5—La1—N4—O8−79.1 (4)
O1—La1—O3—C21176.5 (3)C21—La1—N4—O896.7 (3)
O2—La1—O3—C2132.4 (3)O1—La1—N4—O917.6 (4)
O6'—La1—O3—C21−133.9 (10)O2—La1—N4—O9−176.3 (3)
O2i—La1—O3—C2189.8 (3)O6'—La1—N4—O981.2 (11)
O4—La1—O3—C21−5.8 (3)O2i—La1—N4—O9−122.6 (4)
O9—La1—O3—C21−93.7 (3)O3—La1—N4—O9−58.2 (3)
O5'—La1—O3—C21138.6 (12)O4—La1—N4—O9−105.5 (3)
O6—La1—O3—C21−128.3 (4)O5'—La1—N4—O9106.7 (8)
O5—La1—O3—C21137.1 (3)O6—La1—N4—O996.6 (5)
O8—La1—O3—C21−51.9 (3)O5—La1—N4—O9101.9 (4)
O1—La1—O4—C218.5 (4)O8—La1—N4—O9−179.0 (5)
O2—La1—O4—C21−139.4 (3)C21—La1—N4—O9−82.3 (3)
O6'—La1—O4—C21123.4 (15)La1—O1—C1—C2−94.4 (16)
O2i—La1—O4—C21−72.1 (3)La1—O1—C1—C685.9 (16)
O3—La1—O4—C215.8 (3)O1—C1—C2—C3179.6 (5)
O9—La1—O4—C2190.0 (3)C6—C1—C2—C3−0.7 (7)
O5'—La1—O4—C21−142.6 (15)C1—C2—C3—C40.9 (9)
O6—La1—O4—C21146.3 (5)C2—C3—C4—C5−0.9 (9)
O5—La1—O4—C21−125.1 (5)C3—C4—C5—C7178.6 (6)
O8—La1—O4—C21137.9 (3)C3—C4—C5—C60.6 (8)
O1—La1—O5—N396.7 (6)C9—N1—C6—C5−1.3 (7)
O2—La1—O5—N3−106.5 (6)C9—N1—C6—C1178.5 (4)
O6'—La1—O5—N314.5 (10)C7—C5—C6—N11.1 (7)
O2i—La1—O5—N3−176.0 (6)C4—C5—C6—N1179.3 (5)
O3—La1—O5—N3136.0 (5)C7—C5—C6—C1−178.6 (5)
O4—La1—O5—N3−120.6 (4)C4—C5—C6—C1−0.4 (7)
O9—La1—O5—N318.1 (7)O1—C1—C6—N10.4 (6)
O5'—La1—O5—N3−39 (4)C2—C1—C6—N1−179.3 (4)
O6—La1—O5—N3−2.5 (3)O1—C1—C6—C5−179.8 (4)
O8—La1—O5—N3−34.7 (6)C2—C1—C6—C50.5 (7)
C21—La1—O5—N3−179.0 (4)C4—C5—C7—C8−179.0 (6)
O1—La1—O5'—N3'77.3 (16)C6—C5—C7—C8−1.0 (8)
O2—La1—O5'—N3'−129.3 (18)C5—C7—C8—C91.0 (9)
O6'—La1—O5'—N3'−0.1 (10)C6—N1—C9—C81.2 (7)
O2i—La1—O5'—N3'162.3 (18)C6—N1—C9—C10−179.8 (5)
O3—La1—O5'—N3'114.1 (18)C7—C8—C9—N1−1.0 (8)
O4—La1—O5'—N3'−126.1 (12)C7—C8—C9—C10180.0 (6)
O9—La1—O5'—N3'−6(2)La1—O2—C11—C12−84.2 (5)
O6—La1—O5'—N3'−17.1 (10)La1i—O2—C11—C1289.2 (5)
O5—La1—O5'—N3'120 (5)La1—O2—C11—C1697.3 (4)
O8—La1—O5'—N3'−55.5 (17)La1i—O2—C11—C16−89.2 (4)
C21—La1—O5'—N3'178.0 (13)O2—C11—C12—C13−176.7 (4)
O1—La1—O6—N3−71.0 (6)C16—C11—C12—C131.8 (7)
O2—La1—O6—N373.5 (6)C11—C12—C13—C140.9 (8)
O6'—La1—O6—N3−108 (3)C12—C13—C14—C15−2.1 (8)
O2i—La1—O6—N310.0 (8)C13—C14—C15—C17−179.9 (5)
O3—La1—O6—N3−123.7 (4)C13—C14—C15—C160.6 (7)
O4—La1—O6—N3142.1 (3)C19—N2—C16—C15−2.2 (7)
O9—La1—O6—N3−159.2 (6)C19—N2—C16—C11176.3 (4)
O5'—La1—O6—N310.7 (11)C14—C15—C16—N2−179.4 (4)
O5—La1—O6—N32.5 (3)C17—C15—C16—N21.0 (6)
O8—La1—O6—N3150.5 (7)C14—C15—C16—C112.1 (6)
C21—La1—O6—N3178.9 (4)C17—C15—C16—C11−177.5 (4)
O1—La1—O6'—N3'−92.4 (17)O2—C11—C16—N2−3.2 (6)
O2—La1—O6'—N3'50.8 (19)C12—C11—C16—N2178.2 (4)
O2i—La1—O6'—N3'−23 (2)O2—C11—C16—C15175.3 (4)
O3—La1—O6'—N3'−142.0 (14)C12—C11—C16—C15−3.3 (6)
O4—La1—O6'—N3'137.2 (11)C14—C15—C17—C18−179.3 (5)
O9—La1—O6'—N3'174 (2)C16—C15—C17—C180.3 (7)
O5'—La1—O6'—N3'0.1 (10)C15—C17—C18—C19−0.5 (9)
O6—La1—O6'—N3'49 (2)C16—N2—C19—C182.0 (7)
O5—La1—O6'—N3'−9.5 (12)C16—N2—C19—C20−177.6 (4)
O8—La1—O6'—N3'123 (2)C17—C18—C19—N2−0.5 (8)
C21—La1—O6'—N3'−178.7 (9)C17—C18—C19—C20179.0 (5)
O1—La1—O8—N421.5 (4)La1—O3—C21—O410.7 (5)
O2—La1—O8—N4−177.3 (3)La1—O3—C21—C22−166.5 (5)
O6'—La1—O8—N471.8 (9)La1—O4—C21—O3−10.6 (5)
O2i—La1—O8—N4−154.2 (3)La1—O4—C21—C22166.6 (5)
O3—La1—O8—N4−62.7 (3)O1—La1—C21—O3−3.4 (3)
O4—La1—O8—N4−98.9 (3)O2—La1—C21—O3−151.3 (3)
O9—La1—O8—N4−0.5 (3)O6'—La1—C21—O375.9 (18)
O5'—La1—O8—N4112.3 (7)O2i—La1—C21—O3−85.4 (3)
O6—La1—O8—N486.9 (5)O4—La1—C21—O3169.6 (5)
O5—La1—O8—N4111.6 (3)O9—La1—C21—O382.8 (3)
C21—La1—O8—N4−82.3 (3)O5'—La1—C21—O3−101 (3)
O1—La1—O9—N4−163.5 (3)O6—La1—C21—O3104.1 (9)
O2—La1—O9—N44.5 (4)O5—La1—C21—O3−82.4 (6)
O6'—La1—O9—N4−88.4 (11)O8—La1—C21—O3130.6 (3)
O2i—La1—O9—N4130.4 (3)O1—La1—C21—O4−173.0 (3)
O3—La1—O9—N4120.8 (3)O2—La1—C21—O439.2 (3)
O4—La1—O9—N469.9 (3)O6'—La1—C21—O4−93.6 (18)
O5'—La1—O9—N4−83.2 (9)O2i—La1—C21—O4105.0 (3)
O6—La1—O9—N4−76.0 (4)O3—La1—C21—O4−169.6 (5)
O5—La1—O9—N4−91.6 (4)O9—La1—C21—O4−86.8 (3)
O8—La1—O9—N40.6 (3)O5'—La1—C21—O489 (3)
C21—La1—O9—N495.4 (3)O6—La1—C21—O4−65.5 (9)
La1—O5—N3—O7−175.8 (4)O5—La1—C21—O4108.1 (6)
La1—O5—N3—O64.4 (5)O8—La1—C21—O4−39.0 (3)
La1—O6—N3—O7175.7 (4)

Symmetry codes: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O30.86 (1)2.06 (1)2.910 (5)173 (5)
N2—H2···O40.86 (1)2.20 (3)2.926 (5)143 (5)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5149).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Fazaeli, Y., Najafi, E., Amini, M. M. & Ng, S. W. (2009). Acta Cryst. E65, m711. [PMC free article] [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

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