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Acta Cryst. (2009). E65, m711    [ doi:10.1107/S1600536809019746 ]

Bis([mu]-2-methylquinolin-1-ium-8-olato-[kappa]2O:O')bis[(2-methylquinolin-1-ium-8-olato-[kappa]O)tris(nitrato-[kappa]2O,O')lanthanum(III)]

Y. Fazaeli, E. Najafi, M. M. Amini and S. W. Ng

Abstract top

The two independent N-heterocycles in the centrosymmetric title compound, [La2(C10H9NO)4(NO3)6], exist in the zwitterionic form. One of these binds to one metal center, whereas the other bridges two metal centers. The La atom is chelated by three nitrate groups and is surrounded by nine O atoms in a coordination environment based on a distorted monocapped square-antiprism. The dinuclear structure is further stabilized by intramolecular N-H...O(nitrate) hydrogen bonds.

Related literature top

The N-heterocycle exists in the deprotonated and neutral form in hexakis(µ-2-methylquinolin-8-oxido)bis(2-methylquinolin-8-oxido(2-methyl-8-quinolinol)(nitrato)trilanthanum methanol solvate; see: Katkova et al. (2005).

Experimental top

2-Methyl-8-hydroxyquinoline (0.32 g, 2 mmol) was added to lanthanum nitrate hexahydrate (0.43 g, 1 mmol) in methanol (10 ml). The mixture was stirred for an hour and then filtered. Slow evaporation of solution gave yellow crystals that are stable when heated up to 573 K.

Refinement top

Carbon-bound H-atoms were placed in calculated positions (C—H 0.95 to 0.98 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2 to 1.5U(C). The nitrogen-bound hydrogen atoms were located in a difference Fourier map, and were refined with a distance restraint of N–H 0.88±01 Å; their temperature factors were freely refined.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top
[Figure 1] Fig. 1. Thermal ellipsoid plot (Barbour, 2001) of [La(NO3)3(C10H9NO)2]2; ellipsoids are drawn at the 70% probability level and H atoms of arbitrary radius.
[Figure 2] Fig. 2. Monocapped square-antiprismatic geometry of La.
Bis(µ-2-methylquinolin-1-ium-8-olato-κ2O:O')bis[(2- methylquinolin-1-ium-8-olato-κO)tris(nitrato- κ2O,O')lanthanum(III)] top
Crystal data top
[La2(C10H9NO)4(NO3)6]F(000) = 1272
Mr = 1286.61Dx = 1.859 Mg m−3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 9940 reflections
a = 10.7177 (2) Åθ = 2.3–28.3°
b = 18.3308 (3) ŵ = 1.93 mm−1
c = 12.4473 (2) ÅT = 100 K
β = 109.952 (1)°Block, yellow
V = 2298.67 (7) Å30.20 × 0.15 × 0.10 mm
Z = 2
Data collection top
Bruker SMART APEX
diffractometer		5258 independent reflections
Radiation source: fine-focus sealed tube4897 reflections with I > 2σ(I)
graphiteRint = 0.020
ω scansθmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −13→13
Tmin = 0.699, Tmax = 0.830k = −23→23
28922 measured reflectionsl = −16→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)] = 0.022Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.057H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0293P)2 + 2.866P]
where P = (Fo2 + 2Fc2)/3
5258 reflections(Δ/σ)max = 0.001
344 parametersΔρmax = 0.64 e Å−3
2 restraintsΔρmin = −0.36 e Å−3
Crystal data top
[La2(C10H9NO)4(NO3)6]V = 2298.67 (7) Å3
Mr = 1286.61Z = 2
Monoclinic, P21/nMo Kα radiation
a = 10.7177 (2) ŵ = 1.93 mm−1
b = 18.3308 (3) ÅT = 100 K
c = 12.4473 (2) Å0.20 × 0.15 × 0.10 mm
β = 109.952 (1)°
Data collection top
Bruker SMART APEX
diffractometer		5258 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		4897 reflections with I > 2σ(I)
Tmin = 0.699, Tmax = 0.830Rint = 0.020
28922 measured reflectionsθmax = 27.5°
Refinement top
R[F2 > 2σ(F2)] = 0.022H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.057Δρmax = 0.64 e Å−3
S = 1.05Δρmin = −0.36 e Å−3
5258 reflectionsAbsolute structure: ?
344 parametersFlack parameter: ?
2 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
La10.627521 (11)0.471863 (6)0.661979 (10)0.01366 (5)
O10.39482 (14)0.47330 (8)0.52498 (13)0.0153 (3)
O20.55263 (15)0.38409 (8)0.76113 (14)0.0197 (3)
O30.51647 (17)0.53810 (9)0.79000 (15)0.0241 (3)
O40.57975 (17)0.61199 (9)0.68318 (15)0.0259 (4)
O50.4652 (2)0.65310 (11)0.7854 (2)0.0433 (5)
O60.81044 (17)0.50974 (11)0.84912 (14)0.0281 (4)
O70.84706 (16)0.54647 (10)0.69668 (14)0.0249 (3)
O80.97394 (18)0.58366 (12)0.86437 (17)0.0380 (5)
O90.81082 (16)0.37627 (10)0.69806 (16)0.0287 (4)
O100.63565 (19)0.34935 (10)0.55359 (15)0.0311 (4)
O110.7770 (3)0.26474 (13)0.6382 (2)0.0668 (8)
N10.31296 (18)0.33149 (10)0.50479 (16)0.0185 (4)
H10.379 (2)0.3456 (15)0.483 (2)0.026 (7)*
N20.37563 (17)0.42049 (11)0.86348 (15)0.0178 (4)
H20.423 (2)0.4525 (11)0.842 (2)0.017 (6)*
N30.51907 (19)0.60337 (11)0.75377 (18)0.0234 (4)
N40.87999 (19)0.54744 (12)0.80494 (18)0.0234 (4)
N50.7429 (2)0.32815 (12)0.62974 (19)0.0313 (5)
C10.2499 (2)0.38214 (12)0.54963 (17)0.0156 (4)
C20.2910 (2)0.45585 (12)0.55661 (17)0.0151 (4)
C30.2200 (2)0.50601 (13)0.59584 (19)0.0201 (4)
H30.24320.55620.59910.024*
C40.1140 (2)0.48398 (15)0.6309 (2)0.0255 (5)
H40.06610.51970.65630.031*
C50.0788 (2)0.41235 (15)0.6292 (2)0.0263 (5)
H50.00890.39820.65550.032*
C60.1471 (2)0.35933 (13)0.58808 (18)0.0211 (4)
C70.1194 (2)0.28332 (14)0.5841 (2)0.0281 (5)
H70.05240.26560.61140.034*
C80.1881 (3)0.23603 (13)0.5416 (2)0.0290 (5)
H80.16940.18530.54080.035*
C90.2862 (2)0.26032 (12)0.49867 (19)0.0235 (5)
C100.3615 (3)0.21221 (14)0.4471 (2)0.0340 (6)
H10A0.30160.17540.39910.051*
H10B0.43280.18790.50780.051*
H10C0.39970.24150.40010.051*
C110.3925 (2)0.34856 (12)0.84219 (18)0.0176 (4)
C120.4870 (2)0.33087 (12)0.78824 (18)0.0173 (4)
C130.5007 (2)0.25687 (12)0.76861 (19)0.0213 (4)
H130.56190.24220.73270.026*
C140.4262 (3)0.20362 (13)0.8008 (2)0.0265 (5)
H140.43910.15370.78680.032*
C150.3352 (3)0.22155 (14)0.8518 (2)0.0280 (5)
H150.28590.18450.87270.034*
C160.3157 (2)0.29544 (13)0.87294 (19)0.0222 (5)
C170.2211 (2)0.32082 (15)0.9205 (2)0.0293 (5)
H170.16530.28660.93960.035*
C180.2081 (2)0.39351 (15)0.9397 (2)0.0286 (5)
H180.14460.40930.97250.034*
C190.2892 (2)0.44488 (14)0.91067 (19)0.0229 (5)
C200.2841 (3)0.52479 (14)0.9304 (2)0.0278 (5)
H20A0.33580.55060.89080.042*
H20B0.32160.53491.01250.042*
H20C0.19170.54140.90090.042*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
La10.01291 (7)0.01585 (7)0.01372 (7)−0.00115 (4)0.00648 (5)0.00089 (4)
O10.0135 (7)0.0175 (7)0.0165 (7)−0.0023 (5)0.0073 (6)0.0011 (6)
O20.0205 (7)0.0183 (7)0.0243 (8)0.0005 (6)0.0129 (6)0.0048 (6)
O30.0275 (9)0.0219 (8)0.0293 (9)−0.0028 (6)0.0182 (7)−0.0025 (7)
O40.0336 (9)0.0189 (8)0.0277 (9)−0.0011 (7)0.0135 (7)0.0016 (7)
O50.0421 (11)0.0277 (10)0.0687 (15)0.0063 (8)0.0302 (11)−0.0141 (10)
O60.0249 (9)0.0433 (10)0.0175 (8)−0.0090 (8)0.0092 (7)−0.0023 (7)
O70.0203 (8)0.0363 (9)0.0202 (8)−0.0081 (7)0.0094 (6)−0.0026 (7)
O80.0248 (9)0.0518 (12)0.0333 (10)−0.0167 (8)0.0045 (8)−0.0121 (9)
O90.0206 (8)0.0328 (9)0.0354 (10)0.0050 (7)0.0129 (7)0.0039 (8)
O100.0399 (10)0.0305 (9)0.0211 (9)0.0092 (8)0.0079 (8)−0.0024 (7)
O110.105 (2)0.0392 (13)0.0404 (13)0.0431 (14)0.0049 (13)−0.0060 (10)
N10.0187 (9)0.0173 (9)0.0174 (9)−0.0025 (7)0.0035 (7)0.0021 (7)
N20.0171 (8)0.0223 (9)0.0157 (9)−0.0016 (7)0.0078 (7)0.0035 (7)
N30.0192 (9)0.0204 (9)0.0304 (11)0.0000 (7)0.0083 (8)−0.0055 (8)
N40.0171 (9)0.0310 (10)0.0226 (10)−0.0028 (8)0.0073 (8)−0.0048 (8)
N50.0433 (13)0.0308 (11)0.0245 (11)0.0161 (10)0.0175 (10)0.0032 (9)
C10.0131 (9)0.0205 (10)0.0115 (9)−0.0013 (7)0.0020 (7)0.0037 (8)
C20.0127 (9)0.0200 (10)0.0125 (9)−0.0018 (7)0.0043 (7)0.0022 (8)
C30.0174 (10)0.0232 (11)0.0190 (11)0.0020 (8)0.0056 (8)−0.0012 (9)
C40.0157 (10)0.0415 (14)0.0202 (11)0.0039 (9)0.0073 (8)−0.0029 (10)
C50.0150 (10)0.0476 (15)0.0190 (11)−0.0069 (10)0.0094 (8)0.0013 (10)
C60.0151 (10)0.0315 (12)0.0145 (10)−0.0068 (9)0.0024 (8)0.0056 (9)
C70.0245 (11)0.0354 (14)0.0196 (11)−0.0144 (10)0.0012 (9)0.0093 (10)
C80.0333 (13)0.0218 (11)0.0222 (12)−0.0125 (10)−0.0029 (10)0.0082 (9)
C90.0296 (12)0.0175 (10)0.0157 (10)−0.0024 (9)−0.0021 (9)0.0013 (8)
C100.0449 (15)0.0219 (12)0.0286 (13)0.0047 (11)0.0038 (11)−0.0028 (10)
C110.0173 (9)0.0198 (10)0.0145 (10)−0.0015 (8)0.0039 (8)0.0043 (8)
C120.0174 (10)0.0181 (10)0.0152 (10)−0.0014 (8)0.0039 (8)0.0033 (8)
C130.0255 (11)0.0185 (10)0.0173 (10)0.0017 (8)0.0039 (9)0.0019 (8)
C140.0363 (13)0.0183 (11)0.0201 (11)−0.0044 (9)0.0034 (10)0.0015 (9)
C150.0342 (13)0.0251 (12)0.0222 (12)−0.0117 (10)0.0064 (10)0.0048 (9)
C160.0212 (10)0.0288 (12)0.0150 (10)−0.0074 (9)0.0039 (8)0.0051 (9)
C170.0233 (11)0.0429 (15)0.0236 (12)−0.0098 (10)0.0107 (10)0.0055 (11)
C180.0227 (11)0.0450 (15)0.0234 (12)−0.0038 (10)0.0145 (10)0.0028 (11)
C190.0192 (10)0.0338 (13)0.0162 (11)0.0014 (9)0.0069 (8)0.0020 (9)
C200.0282 (12)0.0333 (13)0.0263 (13)0.0037 (10)0.0148 (10)0.0003 (10)
Geometric parameters (Å, °) top
La1—O22.3308 (15)C4—C51.364 (4)
La1—O1i2.4704 (15)C4—H40.9500
La1—O12.4953 (15)C5—C61.413 (4)
La1—O92.5553 (17)C5—H50.9500
La1—O62.5759 (17)C6—C71.422 (3)
La1—O32.5932 (16)C7—C81.356 (4)
La1—O72.6267 (16)C7—H70.9500
La1—O102.6365 (18)C8—C91.404 (4)
La1—O42.6499 (16)C8—H80.9500
O1—C21.340 (2)C9—C101.482 (4)
O1—La1i2.4704 (15)C10—H10A0.9800
O2—C121.312 (3)C10—H10B0.9800
O3—N31.282 (3)C10—H10C0.9800
O4—N31.269 (3)C11—C161.409 (3)
O5—N31.214 (3)C11—C121.431 (3)
O6—N41.271 (3)C12—C131.395 (3)
O7—N41.271 (3)C13—C141.403 (3)
O8—N41.222 (3)C13—H130.9500
O9—N51.268 (3)C14—C151.373 (4)
O10—N51.276 (3)C14—H140.9500
O11—N51.212 (3)C15—C161.409 (4)
N1—C91.332 (3)C15—H150.9500
N1—C11.374 (3)C16—C171.416 (3)
N1—H10.875 (10)C17—C181.369 (4)
N2—C191.332 (3)C17—H170.9500
N2—C111.369 (3)C18—C191.410 (3)
N2—H20.873 (10)C18—H180.9500
C1—C61.407 (3)C19—C201.489 (3)
C1—C21.414 (3)C20—H20A0.9800
C2—C31.384 (3)C20—H20B0.9800
C3—C41.408 (3)C20—H20C0.9800
C3—H30.9500
O2—La1—O1i147.09 (5)O1—C2—C3123.8 (2)
O2—La1—O185.68 (5)O1—C2—C1118.82 (19)
O1i—La1—O166.36 (6)C3—C2—C1117.34 (19)
O2—La1—O979.43 (5)C2—C3—C4121.2 (2)
O1i—La1—O9105.44 (5)C2—C3—H3119.4
O1—La1—O9131.04 (5)C4—C3—H3119.4
O2—La1—O690.03 (6)C5—C4—C3121.3 (2)
O1i—La1—O6122.78 (5)C5—C4—H4119.4
O1—La1—O6152.87 (5)C3—C4—H4119.4
O9—La1—O673.96 (6)C4—C5—C6119.5 (2)
O2—La1—O371.61 (5)C4—C5—H5120.2
O1i—La1—O3118.10 (5)C6—C5—H5120.2
O1—La1—O381.59 (5)C1—C6—C5118.8 (2)
O9—La1—O3134.40 (6)C1—C6—C7117.2 (2)
O6—La1—O371.66 (6)C5—C6—C7124.0 (2)
O2—La1—O7136.33 (5)C8—C7—C6120.4 (2)
O1i—La1—O774.72 (5)C8—C7—H7119.8
O1—La1—O7137.50 (5)C6—C7—H7119.8
O9—La1—O774.71 (6)C7—C8—C9121.5 (2)
O6—La1—O749.33 (5)C7—C8—H8119.3
O3—La1—O7103.20 (5)C9—C8—H8119.3
O2—La1—O1076.14 (6)N1—C9—C8117.6 (2)
O1i—La1—O1082.77 (5)N1—C9—C10118.0 (2)
O1—La1—O1081.90 (5)C8—C9—C10124.4 (2)
O9—La1—O1049.32 (6)C9—C10—H10A109.5
O6—La1—O10122.99 (6)C9—C10—H10B109.5
O3—La1—O10144.64 (6)H10A—C10—H10B109.5
O7—La1—O10110.09 (6)C9—C10—H10C109.5
O2—La1—O4120.22 (5)H10A—C10—H10C109.5
O1i—La1—O474.90 (5)H10B—C10—H10C109.5
O1—La1—O482.87 (5)N2—C11—C16119.0 (2)
O9—La1—O4144.12 (6)N2—C11—C12118.05 (19)
O6—La1—O476.23 (6)C16—C11—C12122.9 (2)
O3—La1—O448.71 (5)O2—C12—C13125.5 (2)
O7—La1—O470.83 (5)O2—C12—C11118.66 (19)
O10—La1—O4156.62 (5)C13—C12—C11115.9 (2)
C2—O1—La1i123.42 (12)C12—C13—C14121.5 (2)
C2—O1—La1122.24 (12)C12—C13—H13119.3
La1i—O1—La1113.64 (6)C14—C13—H13119.3
C12—O2—La1163.94 (14)C15—C14—C13121.9 (2)
N3—O3—La198.69 (13)C15—C14—H14119.0
N3—O4—La196.33 (12)C13—C14—H14119.0
N4—O6—La197.65 (13)C14—C15—C16119.4 (2)
N4—O7—La195.21 (12)C14—C15—H15120.3
N5—O9—La197.36 (13)C16—C15—H15120.3
N5—O10—La193.33 (13)C11—C16—C15118.4 (2)
C9—N1—C1124.0 (2)C11—C16—C17117.0 (2)
C9—N1—H1116.9 (19)C15—C16—C17124.5 (2)
C1—N1—H1119.0 (19)C18—C17—C16121.5 (2)
C19—N2—C11124.5 (2)C18—C17—H17119.3
C19—N2—H2118.1 (18)C16—C17—H17119.3
C11—N2—H2117.4 (18)C17—C18—C19119.8 (2)
O5—N3—O4122.9 (2)C17—C18—H18120.1
O5—N3—O3121.1 (2)C19—C18—H18120.1
O4—N3—O3115.96 (18)N2—C19—C18118.1 (2)
O8—N4—O6121.1 (2)N2—C19—C20118.2 (2)
O8—N4—O7121.5 (2)C18—C19—C20123.7 (2)
O6—N4—O7117.34 (18)C19—C20—H20A109.5
O11—N5—O9121.4 (2)C19—C20—H20B109.5
O11—N5—O10121.7 (3)H20A—C20—H20B109.5
O9—N5—O10116.9 (2)C19—C20—H20C109.5
N1—C1—C6119.2 (2)H20A—C20—H20C109.5
N1—C1—C2119.01 (18)H20B—C20—H20C109.5
C6—C1—C2121.8 (2)
O2—La1—O1—C227.09 (15)O6—La1—O10—N52.99 (16)
O1i—La1—O1—C2−170.71 (18)O3—La1—O10—N5−102.47 (16)
O9—La1—O1—C299.05 (15)O7—La1—O10—N556.84 (15)
O6—La1—O1—C2−54.5 (2)O4—La1—O10—N5144.81 (15)
O3—La1—O1—C2−44.94 (15)La1—O4—N3—O5−173.9 (2)
O7—La1—O1—C2−145.33 (14)La1—O4—N3—O35.5 (2)
O10—La1—O1—C2103.68 (15)La1—O3—N3—O5173.8 (2)
O4—La1—O1—C2−94.12 (15)La1—O3—N3—O4−5.7 (2)
O2—La1—O1—La1i−162.20 (7)La1—O6—N4—O8172.3 (2)
O1i—La1—O1—La1i0.0La1—O6—N4—O7−7.0 (2)
O9—La1—O1—La1i−90.24 (8)La1—O7—N4—O8−172.5 (2)
O6—La1—O1—La1i116.21 (11)La1—O7—N4—O66.8 (2)
O3—La1—O1—La1i125.77 (6)La1—O9—N5—O11−160.3 (2)
O7—La1—O1—La1i25.38 (10)La1—O9—N5—O1018.1 (2)
O10—La1—O1—La1i−85.61 (7)La1—O10—N5—O11161.0 (3)
O4—La1—O1—La1i76.59 (6)La1—O10—N5—O9−17.4 (2)
O1i—La1—O2—C12−2.5 (6)C9—N1—C1—C6−2.5 (3)
O1—La1—O2—C1228.6 (5)C9—N1—C1—C2177.0 (2)
O9—La1—O2—C12−104.6 (5)La1i—O1—C2—C3−79.0 (2)
O6—La1—O2—C12−178.2 (5)La1—O1—C2—C390.8 (2)
O3—La1—O2—C12111.1 (5)La1i—O1—C2—C1100.81 (19)
O7—La1—O2—C12−158.8 (5)La1—O1—C2—C1−89.4 (2)
O10—La1—O2—C12−54.1 (5)N1—C1—C2—O1−3.6 (3)
O4—La1—O2—C12107.7 (5)C6—C1—C2—O1175.98 (19)
O2—La1—O3—N3−172.85 (14)N1—C1—C2—C3176.21 (19)
O1i—La1—O3—N3−27.22 (14)C6—C1—C2—C3−4.2 (3)
O1—La1—O3—N3−84.63 (13)O1—C2—C3—C4−178.2 (2)
O9—La1—O3—N3133.73 (13)C1—C2—C3—C42.1 (3)
O6—La1—O3—N390.79 (13)C2—C3—C4—C51.0 (4)
O7—La1—O3—N352.32 (14)C3—C4—C5—C6−2.0 (4)
O10—La1—O3—N3−147.60 (12)N1—C1—C6—C5−177.14 (19)
O4—La1—O3—N33.24 (12)C2—C1—C6—C53.3 (3)
O2—La1—O4—N31.05 (15)N1—C1—C6—C73.6 (3)
O1i—La1—O4—N3149.16 (13)C2—C1—C6—C7−176.0 (2)
O1—La1—O4—N381.80 (13)C4—C5—C6—C1−0.1 (3)
O9—La1—O4—N3−115.25 (14)C4—C5—C6—C7179.1 (2)
O6—La1—O4—N3−80.79 (13)C1—C6—C7—C8−1.8 (3)
O3—La1—O4—N3−3.25 (12)C5—C6—C7—C8178.9 (2)
O7—La1—O4—N3−132.09 (14)C6—C7—C8—C9−1.1 (4)
O10—La1—O4—N3131.47 (16)C1—N1—C9—C8−0.5 (3)
O2—La1—O6—N4166.36 (14)C1—N1—C9—C10179.4 (2)
O1i—La1—O6—N4−10.92 (16)C7—C8—C9—N12.3 (3)
O1—La1—O6—N4−113.08 (15)C7—C8—C9—C10−177.6 (2)
O9—La1—O6—N487.38 (14)C19—N2—C11—C16−0.9 (3)
O3—La1—O6—N4−123.06 (15)C19—N2—C11—C12178.4 (2)
O7—La1—O6—N43.96 (12)La1—O2—C12—C1375.9 (6)
O10—La1—O6—N492.94 (15)La1—O2—C12—C11−103.9 (5)
O4—La1—O6—N4−72.44 (14)N2—C11—C12—O2−0.3 (3)
O2—La1—O7—N4−29.91 (17)C16—C11—C12—O2178.99 (19)
O1i—La1—O7—N4163.12 (14)N2—C11—C12—C13179.88 (19)
O1—La1—O7—N4139.10 (12)C16—C11—C12—C13−0.8 (3)
O9—La1—O7—N4−85.73 (14)O2—C12—C13—C14179.9 (2)
O6—La1—O7—N4−3.94 (13)C11—C12—C13—C14−0.3 (3)
O3—La1—O7—N447.18 (14)C12—C13—C14—C150.8 (4)
O10—La1—O7—N4−120.70 (13)C13—C14—C15—C16−0.1 (4)
O4—La1—O7—N484.13 (13)N2—C11—C16—C15−179.2 (2)
O2—La1—O9—N570.58 (14)C12—C11—C16—C151.4 (3)
O1i—La1—O9—N5−75.98 (14)N2—C11—C16—C172.4 (3)
O1—La1—O9—N5−4.11 (16)C12—C11—C16—C17−176.9 (2)
O6—La1—O9—N5163.69 (15)C14—C15—C16—C11−1.0 (3)
O3—La1—O9—N5121.40 (14)C14—C15—C16—C17177.2 (2)
O7—La1—O9—N5−144.95 (14)C11—C16—C17—C18−2.3 (4)
O10—La1—O9—N5−10.16 (13)C15—C16—C17—C18179.4 (2)
O4—La1—O9—N5−161.43 (13)C16—C17—C18—C190.7 (4)
O2—La1—O10—N5−77.84 (14)C11—N2—C19—C18−0.8 (3)
O1i—La1—O10—N5127.61 (14)C11—N2—C19—C20178.9 (2)
O1—La1—O10—N5−165.36 (14)C17—C18—C19—N20.9 (4)
O9—La1—O10—N510.04 (13)C17—C18—C19—C20−178.8 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.88 (1)2.39 (2)3.115 (3)140 (2)
N2—H2···O30.87 (1)2.08 (1)2.950 (2)173 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O4i0.88 (1)2.39 (2)3.115 (3)140 (2)
N2—H2···O30.87 (1)2.08 (1)2.950 (2)173 (2)
Symmetry codes: (i) −x+1, −y+1, −z+1.
Acknowledgements top

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

references
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