Bis(μ-2-methyl­quinolin-1-ium-8-olato-κ2O:O′)bis­[(2-methyl­quinolin-1-ium-8-olato-κO)tris­(nitrato-κ2O,O′)lanthanum(III)]

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

doi:10.1107/S1600536809019746

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m711

doi:10.1107/S1600536809019746

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Bis(μ-2-methylquinolin-1-ium-8-olato-κ²O:O′)bis[(2-methylquinolin-1-ium-8-olato-κO)tris(nitrato-κ²O,O′)lanthanum(III)]

Yousef Fazaeli,^a Ezzatollah Najafi,^a Mostafa M. Amini ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, General Campus, Shahid Beheshti University, Tehran 1983963113, Iran, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 19 May 2009; accepted 25 May 2009; online 6 June 2009)

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

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

Crystal data

[La₂(C₁₀H₉NO)₄(NO₃)₆]
M_r = 1286.61
Monoclinic, P 2₁ /n
a = 10.7177 (2) Å
b = 18.3308 (3) Å
c = 12.4473 (2) Å
β = 109.952 (1)°
V = 2298.67 (7) Å³
Z = 2
Mo Kα radiation
μ = 1.93 mm⁻¹
T = 100 K
0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.699, T_max = 0.830
28922 measured reflections
5258 independent reflections
4897 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.057
S = 1.05
5258 reflections
344 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.64 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4ⁱ	0.88 (1)	2.39 (2)	3.115 (3)	140 (2)
N2—H2⋯O3	0.87 (1)	2.08 (1)	2.950 (2)	173 (2)
Symmetry code: (i) -x+1, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; 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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019746/tk2454sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019746/tk2454Isup2.hkl

checkCIF report

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.

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

	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.
	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
M_r = 1286.61	D_x = 1.859 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9940 reflections
a = 10.7177 (2) Å	θ = 2.3–28.3°
b = 18.3308 (3) Å	µ = 1.93 mm⁻¹
c = 12.4473 (2) Å	T = 100 K
β = 109.952 (1)°	Block, yellow
V = 2298.67 (7) Å³	0.20 × 0.15 × 0.10 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	5258 independent reflections
Radiation source: fine-focus sealed tube	4897 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω scans	θ_max = 27.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.699, T_max = 0.830	k = −23→23
28922 measured reflections	l = −16→15

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.057	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0293P)² + 2.866P] where P = (F_o² + 2F_c²)/3
5258 reflections	(Δ/σ)_max = 0.001
344 parameters	Δρ_max = 0.64 e Å⁻³
2 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

[La₂(C₁₀H₉NO)₄(NO₃)₆]	V = 2298.67 (7) Å³
M_r = 1286.61	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.7177 (2) Å	µ = 1.93 mm⁻¹
b = 18.3308 (3) Å	T = 100 K
c = 12.4473 (2) Å	0.20 × 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)
T_min = 0.699, T_max = 0.830	R_int = 0.020
28922 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	2 restraints
wR(F²) = 0.057	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.64 e Å⁻³
5258 reflections	Δρ_min = −0.36 e Å⁻³
344 parameters

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

	x	y	z	U_iso*/U_eq
La1	0.627521 (11)	0.471863 (6)	0.661979 (10)	0.01366 (5)
O1	0.39482 (14)	0.47330 (8)	0.52498 (13)	0.0153 (3)
O2	0.55263 (15)	0.38409 (8)	0.76113 (14)	0.0197 (3)
O3	0.51647 (17)	0.53810 (9)	0.79000 (15)	0.0241 (3)
O4	0.57975 (17)	0.61199 (9)	0.68318 (15)	0.0259 (4)
O5	0.4652 (2)	0.65310 (11)	0.7854 (2)	0.0433 (5)
O6	0.81044 (17)	0.50974 (11)	0.84912 (14)	0.0281 (4)
O7	0.84706 (16)	0.54647 (10)	0.69668 (14)	0.0249 (3)
O8	0.97394 (18)	0.58366 (12)	0.86437 (17)	0.0380 (5)
O9	0.81082 (16)	0.37627 (10)	0.69806 (16)	0.0287 (4)
O10	0.63565 (19)	0.34935 (10)	0.55359 (15)	0.0311 (4)
O11	0.7770 (3)	0.26474 (13)	0.6382 (2)	0.0668 (8)
N1	0.31296 (18)	0.33149 (10)	0.50479 (16)	0.0185 (4)
H1	0.379 (2)	0.3456 (15)	0.483 (2)	0.026 (7)*
N2	0.37563 (17)	0.42049 (11)	0.86348 (15)	0.0178 (4)
H2	0.423 (2)	0.4525 (11)	0.842 (2)	0.017 (6)*
N3	0.51907 (19)	0.60337 (11)	0.75377 (18)	0.0234 (4)
N4	0.87999 (19)	0.54744 (12)	0.80494 (18)	0.0234 (4)
N5	0.7429 (2)	0.32815 (12)	0.62974 (19)	0.0313 (5)
C1	0.2499 (2)	0.38214 (12)	0.54963 (17)	0.0156 (4)
C2	0.2910 (2)	0.45585 (12)	0.55661 (17)	0.0151 (4)
C3	0.2200 (2)	0.50601 (13)	0.59584 (19)	0.0201 (4)
H3	0.2432	0.5562	0.5991	0.024*
C4	0.1140 (2)	0.48398 (15)	0.6309 (2)	0.0255 (5)
H4	0.0661	0.5197	0.6563	0.031*
C5	0.0788 (2)	0.41235 (15)	0.6292 (2)	0.0263 (5)
H5	0.0089	0.3982	0.6555	0.032*
C6	0.1471 (2)	0.35933 (13)	0.58808 (18)	0.0211 (4)
C7	0.1194 (2)	0.28332 (14)	0.5841 (2)	0.0281 (5)
H7	0.0524	0.2656	0.6114	0.034*
C8	0.1881 (3)	0.23603 (13)	0.5416 (2)	0.0290 (5)
H8	0.1694	0.1853	0.5408	0.035*
C9	0.2862 (2)	0.26032 (12)	0.49867 (19)	0.0235 (5)
C10	0.3615 (3)	0.21221 (14)	0.4471 (2)	0.0340 (6)
H10A	0.3016	0.1754	0.3991	0.051*
H10B	0.4328	0.1879	0.5078	0.051*
H10C	0.3997	0.2415	0.4001	0.051*
C11	0.3925 (2)	0.34856 (12)	0.84219 (18)	0.0176 (4)
C12	0.4870 (2)	0.33087 (12)	0.78824 (18)	0.0173 (4)
C13	0.5007 (2)	0.25687 (12)	0.76861 (19)	0.0213 (4)
H13	0.5619	0.2422	0.7327	0.026*
C14	0.4262 (3)	0.20362 (13)	0.8008 (2)	0.0265 (5)
H14	0.4391	0.1537	0.7868	0.032*
C15	0.3352 (3)	0.22155 (14)	0.8518 (2)	0.0280 (5)
H15	0.2859	0.1845	0.8727	0.034*
C16	0.3157 (2)	0.29544 (13)	0.87294 (19)	0.0222 (5)
C17	0.2211 (2)	0.32082 (15)	0.9205 (2)	0.0293 (5)
H17	0.1653	0.2866	0.9396	0.035*
C18	0.2081 (2)	0.39351 (15)	0.9397 (2)	0.0286 (5)
H18	0.1446	0.4093	0.9725	0.034*
C19	0.2892 (2)	0.44488 (14)	0.91067 (19)	0.0229 (5)
C20	0.2841 (3)	0.52479 (14)	0.9304 (2)	0.0278 (5)
H20A	0.3358	0.5506	0.8908	0.042*
H20B	0.3216	0.5349	1.0125	0.042*
H20C	0.1917	0.5414	0.9009	0.042*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
La1	0.01291 (7)	0.01585 (7)	0.01372 (7)	−0.00115 (4)	0.00648 (5)	0.00089 (4)
O1	0.0135 (7)	0.0175 (7)	0.0165 (7)	−0.0023 (5)	0.0073 (6)	0.0011 (6)
O2	0.0205 (7)	0.0183 (7)	0.0243 (8)	0.0005 (6)	0.0129 (6)	0.0048 (6)
O3	0.0275 (9)	0.0219 (8)	0.0293 (9)	−0.0028 (6)	0.0182 (7)	−0.0025 (7)
O4	0.0336 (9)	0.0189 (8)	0.0277 (9)	−0.0011 (7)	0.0135 (7)	0.0016 (7)
O5	0.0421 (11)	0.0277 (10)	0.0687 (15)	0.0063 (8)	0.0302 (11)	−0.0141 (10)
O6	0.0249 (9)	0.0433 (10)	0.0175 (8)	−0.0090 (8)	0.0092 (7)	−0.0023 (7)
O7	0.0203 (8)	0.0363 (9)	0.0202 (8)	−0.0081 (7)	0.0094 (6)	−0.0026 (7)
O8	0.0248 (9)	0.0518 (12)	0.0333 (10)	−0.0167 (8)	0.0045 (8)	−0.0121 (9)
O9	0.0206 (8)	0.0328 (9)	0.0354 (10)	0.0050 (7)	0.0129 (7)	0.0039 (8)
O10	0.0399 (10)	0.0305 (9)	0.0211 (9)	0.0092 (8)	0.0079 (8)	−0.0024 (7)
O11	0.105 (2)	0.0392 (13)	0.0404 (13)	0.0431 (14)	0.0049 (13)	−0.0060 (10)
N1	0.0187 (9)	0.0173 (9)	0.0174 (9)	−0.0025 (7)	0.0035 (7)	0.0021 (7)
N2	0.0171 (8)	0.0223 (9)	0.0157 (9)	−0.0016 (7)	0.0078 (7)	0.0035 (7)
N3	0.0192 (9)	0.0204 (9)	0.0304 (11)	0.0000 (7)	0.0083 (8)	−0.0055 (8)
N4	0.0171 (9)	0.0310 (10)	0.0226 (10)	−0.0028 (8)	0.0073 (8)	−0.0048 (8)
N5	0.0433 (13)	0.0308 (11)	0.0245 (11)	0.0161 (10)	0.0175 (10)	0.0032 (9)
C1	0.0131 (9)	0.0205 (10)	0.0115 (9)	−0.0013 (7)	0.0020 (7)	0.0037 (8)
C2	0.0127 (9)	0.0200 (10)	0.0125 (9)	−0.0018 (7)	0.0043 (7)	0.0022 (8)
C3	0.0174 (10)	0.0232 (11)	0.0190 (11)	0.0020 (8)	0.0056 (8)	−0.0012 (9)
C4	0.0157 (10)	0.0415 (14)	0.0202 (11)	0.0039 (9)	0.0073 (8)	−0.0029 (10)
C5	0.0150 (10)	0.0476 (15)	0.0190 (11)	−0.0069 (10)	0.0094 (8)	0.0013 (10)
C6	0.0151 (10)	0.0315 (12)	0.0145 (10)	−0.0068 (9)	0.0024 (8)	0.0056 (9)
C7	0.0245 (11)	0.0354 (14)	0.0196 (11)	−0.0144 (10)	0.0012 (9)	0.0093 (10)
C8	0.0333 (13)	0.0218 (11)	0.0222 (12)	−0.0125 (10)	−0.0029 (10)	0.0082 (9)
C9	0.0296 (12)	0.0175 (10)	0.0157 (10)	−0.0024 (9)	−0.0021 (9)	0.0013 (8)
C10	0.0449 (15)	0.0219 (12)	0.0286 (13)	0.0047 (11)	0.0038 (11)	−0.0028 (10)
C11	0.0173 (9)	0.0198 (10)	0.0145 (10)	−0.0015 (8)	0.0039 (8)	0.0043 (8)
C12	0.0174 (10)	0.0181 (10)	0.0152 (10)	−0.0014 (8)	0.0039 (8)	0.0033 (8)
C13	0.0255 (11)	0.0185 (10)	0.0173 (10)	0.0017 (8)	0.0039 (9)	0.0019 (8)
C14	0.0363 (13)	0.0183 (11)	0.0201 (11)	−0.0044 (9)	0.0034 (10)	0.0015 (9)
C15	0.0342 (13)	0.0251 (12)	0.0222 (12)	−0.0117 (10)	0.0064 (10)	0.0048 (9)
C16	0.0212 (10)	0.0288 (12)	0.0150 (10)	−0.0074 (9)	0.0039 (8)	0.0051 (9)
C17	0.0233 (11)	0.0429 (15)	0.0236 (12)	−0.0098 (10)	0.0107 (10)	0.0055 (11)
C18	0.0227 (11)	0.0450 (15)	0.0234 (12)	−0.0038 (10)	0.0145 (10)	0.0028 (11)
C19	0.0192 (10)	0.0338 (13)	0.0162 (11)	0.0014 (9)	0.0069 (8)	0.0020 (9)
C20	0.0282 (12)	0.0333 (13)	0.0263 (13)	0.0037 (10)	0.0148 (10)	0.0003 (10)

Geometric parameters (Å, º) top

La1—O2	2.3308 (15)	C4—C5	1.364 (4)
La1—O1ⁱ	2.4704 (15)	C4—H4	0.9500
La1—O1	2.4953 (15)	C5—C6	1.413 (4)
La1—O9	2.5553 (17)	C5—H5	0.9500
La1—O6	2.5759 (17)	C6—C7	1.422 (3)
La1—O3	2.5932 (16)	C7—C8	1.356 (4)
La1—O7	2.6267 (16)	C7—H7	0.9500
La1—O10	2.6365 (18)	C8—C9	1.404 (4)
La1—O4	2.6499 (16)	C8—H8	0.9500
O1—C2	1.340 (2)	C9—C10	1.482 (4)
O1—La1ⁱ	2.4704 (15)	C10—H10A	0.9800
O2—C12	1.312 (3)	C10—H10B	0.9800
O3—N3	1.282 (3)	C10—H10C	0.9800
O4—N3	1.269 (3)	C11—C16	1.409 (3)
O5—N3	1.214 (3)	C11—C12	1.431 (3)
O6—N4	1.271 (3)	C12—C13	1.395 (3)
O7—N4	1.271 (3)	C13—C14	1.403 (3)
O8—N4	1.222 (3)	C13—H13	0.9500
O9—N5	1.268 (3)	C14—C15	1.373 (4)
O10—N5	1.276 (3)	C14—H14	0.9500
O11—N5	1.212 (3)	C15—C16	1.409 (4)
N1—C9	1.332 (3)	C15—H15	0.9500
N1—C1	1.374 (3)	C16—C17	1.416 (3)
N1—H1	0.875 (10)	C17—C18	1.369 (4)
N2—C19	1.332 (3)	C17—H17	0.9500
N2—C11	1.369 (3)	C18—C19	1.410 (3)
N2—H2	0.873 (10)	C18—H18	0.9500
C1—C6	1.407 (3)	C19—C20	1.489 (3)
C1—C2	1.414 (3)	C20—H20A	0.9800
C2—C3	1.384 (3)	C20—H20B	0.9800
C3—C4	1.408 (3)	C20—H20C	0.9800
C3—H3	0.9500

O2—La1—O1ⁱ	147.09 (5)	O1—C2—C3	123.8 (2)
O2—La1—O1	85.68 (5)	O1—C2—C1	118.82 (19)
O1ⁱ—La1—O1	66.36 (6)	C3—C2—C1	117.34 (19)
O2—La1—O9	79.43 (5)	C2—C3—C4	121.2 (2)
O1ⁱ—La1—O9	105.44 (5)	C2—C3—H3	119.4
O1—La1—O9	131.04 (5)	C4—C3—H3	119.4
O2—La1—O6	90.03 (6)	C5—C4—C3	121.3 (2)
O1ⁱ—La1—O6	122.78 (5)	C5—C4—H4	119.4
O1—La1—O6	152.87 (5)	C3—C4—H4	119.4
O9—La1—O6	73.96 (6)	C4—C5—C6	119.5 (2)
O2—La1—O3	71.61 (5)	C4—C5—H5	120.2
O1ⁱ—La1—O3	118.10 (5)	C6—C5—H5	120.2
O1—La1—O3	81.59 (5)	C1—C6—C5	118.8 (2)
O9—La1—O3	134.40 (6)	C1—C6—C7	117.2 (2)
O6—La1—O3	71.66 (6)	C5—C6—C7	124.0 (2)
O2—La1—O7	136.33 (5)	C8—C7—C6	120.4 (2)
O1ⁱ—La1—O7	74.72 (5)	C8—C7—H7	119.8
O1—La1—O7	137.50 (5)	C6—C7—H7	119.8
O9—La1—O7	74.71 (6)	C7—C8—C9	121.5 (2)
O6—La1—O7	49.33 (5)	C7—C8—H8	119.3
O3—La1—O7	103.20 (5)	C9—C8—H8	119.3
O2—La1—O10	76.14 (6)	N1—C9—C8	117.6 (2)
O1ⁱ—La1—O10	82.77 (5)	N1—C9—C10	118.0 (2)
O1—La1—O10	81.90 (5)	C8—C9—C10	124.4 (2)
O9—La1—O10	49.32 (6)	C9—C10—H10A	109.5
O6—La1—O10	122.99 (6)	C9—C10—H10B	109.5
O3—La1—O10	144.64 (6)	H10A—C10—H10B	109.5
O7—La1—O10	110.09 (6)	C9—C10—H10C	109.5
O2—La1—O4	120.22 (5)	H10A—C10—H10C	109.5
O1ⁱ—La1—O4	74.90 (5)	H10B—C10—H10C	109.5
O1—La1—O4	82.87 (5)	N2—C11—C16	119.0 (2)
O9—La1—O4	144.12 (6)	N2—C11—C12	118.05 (19)
O6—La1—O4	76.23 (6)	C16—C11—C12	122.9 (2)
O3—La1—O4	48.71 (5)	O2—C12—C13	125.5 (2)
O7—La1—O4	70.83 (5)	O2—C12—C11	118.66 (19)
O10—La1—O4	156.62 (5)	C13—C12—C11	115.9 (2)
C2—O1—La1ⁱ	123.42 (12)	C12—C13—C14	121.5 (2)
C2—O1—La1	122.24 (12)	C12—C13—H13	119.3
La1ⁱ—O1—La1	113.64 (6)	C14—C13—H13	119.3
C12—O2—La1	163.94 (14)	C15—C14—C13	121.9 (2)
N3—O3—La1	98.69 (13)	C15—C14—H14	119.0
N3—O4—La1	96.33 (12)	C13—C14—H14	119.0
N4—O6—La1	97.65 (13)	C14—C15—C16	119.4 (2)
N4—O7—La1	95.21 (12)	C14—C15—H15	120.3
N5—O9—La1	97.36 (13)	C16—C15—H15	120.3
N5—O10—La1	93.33 (13)	C11—C16—C15	118.4 (2)
C9—N1—C1	124.0 (2)	C11—C16—C17	117.0 (2)
C9—N1—H1	116.9 (19)	C15—C16—C17	124.5 (2)
C1—N1—H1	119.0 (19)	C18—C17—C16	121.5 (2)
C19—N2—C11	124.5 (2)	C18—C17—H17	119.3
C19—N2—H2	118.1 (18)	C16—C17—H17	119.3
C11—N2—H2	117.4 (18)	C17—C18—C19	119.8 (2)
O5—N3—O4	122.9 (2)	C17—C18—H18	120.1
O5—N3—O3	121.1 (2)	C19—C18—H18	120.1
O4—N3—O3	115.96 (18)	N2—C19—C18	118.1 (2)
O8—N4—O6	121.1 (2)	N2—C19—C20	118.2 (2)
O8—N4—O7	121.5 (2)	C18—C19—C20	123.7 (2)
O6—N4—O7	117.34 (18)	C19—C20—H20A	109.5
O11—N5—O9	121.4 (2)	C19—C20—H20B	109.5
O11—N5—O10	121.7 (3)	H20A—C20—H20B	109.5
O9—N5—O10	116.9 (2)	C19—C20—H20C	109.5
N1—C1—C6	119.2 (2)	H20A—C20—H20C	109.5
N1—C1—C2	119.01 (18)	H20B—C20—H20C	109.5
C6—C1—C2	121.8 (2)

O2—La1—O1—C2	27.09 (15)	O6—La1—O10—N5	2.99 (16)
O1ⁱ—La1—O1—C2	−170.71 (18)	O3—La1—O10—N5	−102.47 (16)
O9—La1—O1—C2	99.05 (15)	O7—La1—O10—N5	56.84 (15)
O6—La1—O1—C2	−54.5 (2)	O4—La1—O10—N5	144.81 (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—O3	5.5 (2)
O10—La1—O1—C2	103.68 (15)	La1—O3—N3—O5	173.8 (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—O8	172.3 (2)
O1ⁱ—La1—O1—La1ⁱ	0.0	La1—O6—N4—O7	−7.0 (2)
O9—La1—O1—La1ⁱ	−90.24 (8)	La1—O7—N4—O8	−172.5 (2)
O6—La1—O1—La1ⁱ	116.21 (11)	La1—O7—N4—O6	6.8 (2)
O3—La1—O1—La1ⁱ	125.77 (6)	La1—O9—N5—O11	−160.3 (2)
O7—La1—O1—La1ⁱ	25.38 (10)	La1—O9—N5—O10	18.1 (2)
O10—La1—O1—La1ⁱ	−85.61 (7)	La1—O10—N5—O11	161.0 (3)
O4—La1—O1—La1ⁱ	76.59 (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—C12	28.6 (5)	C9—N1—C1—C2	177.0 (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—C3	90.8 (2)
O3—La1—O2—C12	111.1 (5)	La1ⁱ—O1—C2—C1	100.81 (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—C12	107.7 (5)	C6—C1—C2—O1	175.98 (19)
O2—La1—O3—N3	−172.85 (14)	N1—C1—C2—C3	176.21 (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—N3	133.73 (13)	C1—C2—C3—C4	2.1 (3)
O6—La1—O3—N3	90.79 (13)	C2—C3—C4—C5	1.0 (4)
O7—La1—O3—N3	52.32 (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—N3	3.24 (12)	C2—C1—C6—C5	3.3 (3)
O2—La1—O4—N3	1.05 (15)	N1—C1—C6—C7	3.6 (3)
O1ⁱ—La1—O4—N3	149.16 (13)	C2—C1—C6—C7	−176.0 (2)
O1—La1—O4—N3	81.80 (13)	C4—C5—C6—C1	−0.1 (3)
O9—La1—O4—N3	−115.25 (14)	C4—C5—C6—C7	179.1 (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—C8	178.9 (2)
O7—La1—O4—N3	−132.09 (14)	C6—C7—C8—C9	−1.1 (4)
O10—La1—O4—N3	131.47 (16)	C1—N1—C9—C8	−0.5 (3)
O2—La1—O6—N4	166.36 (14)	C1—N1—C9—C10	179.4 (2)
O1ⁱ—La1—O6—N4	−10.92 (16)	C7—C8—C9—N1	2.3 (3)
O1—La1—O6—N4	−113.08 (15)	C7—C8—C9—C10	−177.6 (2)
O9—La1—O6—N4	87.38 (14)	C19—N2—C11—C16	−0.9 (3)
O3—La1—O6—N4	−123.06 (15)	C19—N2—C11—C12	178.4 (2)
O7—La1—O6—N4	3.96 (12)	La1—O2—C12—C13	75.9 (6)
O10—La1—O6—N4	92.94 (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—O2	178.99 (19)
O1ⁱ—La1—O7—N4	163.12 (14)	N2—C11—C12—C13	179.88 (19)
O1—La1—O7—N4	139.10 (12)	C16—C11—C12—C13	−0.8 (3)
O9—La1—O7—N4	−85.73 (14)	O2—C12—C13—C14	179.9 (2)
O6—La1—O7—N4	−3.94 (13)	C11—C12—C13—C14	−0.3 (3)
O3—La1—O7—N4	47.18 (14)	C12—C13—C14—C15	0.8 (4)
O10—La1—O7—N4	−120.70 (13)	C13—C14—C15—C16	−0.1 (4)
O4—La1—O7—N4	84.13 (13)	N2—C11—C16—C15	−179.2 (2)
O2—La1—O9—N5	70.58 (14)	C12—C11—C16—C15	1.4 (3)
O1ⁱ—La1—O9—N5	−75.98 (14)	N2—C11—C16—C17	2.4 (3)
O1—La1—O9—N5	−4.11 (16)	C12—C11—C16—C17	−176.9 (2)
O6—La1—O9—N5	163.69 (15)	C14—C15—C16—C11	−1.0 (3)
O3—La1—O9—N5	121.40 (14)	C14—C15—C16—C17	177.2 (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—C18	179.4 (2)
O4—La1—O9—N5	−161.43 (13)	C16—C17—C18—C19	0.7 (4)
O2—La1—O10—N5	−77.84 (14)	C11—N2—C19—C18	−0.8 (3)
O1ⁱ—La1—O10—N5	127.61 (14)	C11—N2—C19—C20	178.9 (2)
O1—La1—O10—N5	−165.36 (14)	C17—C18—C19—N2	0.9 (4)
O9—La1—O10—N5	10.04 (13)	C17—C18—C19—C20	−178.8 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.88 (1)	2.39 (2)	3.115 (3)	140 (2)
N2—H2···O3	0.87 (1)	2.08 (1)	2.950 (2)	173 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[La₂(C₁₀H₉NO)₄(NO₃)₆]
M_r	1286.61
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.7177 (2), 18.3308 (3), 12.4473 (2)
β (°)	109.952 (1)
V (Å³)	2298.67 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.93
Crystal size (mm)	0.20 × 0.15 × 0.10

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.699, 0.830
No. of measured, independent and observed [I > 2σ(I)] reflections	28922, 5258, 4897
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.057, 1.05
No. of reflections	5258
No. of parameters	344
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.64, −0.36

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4ⁱ	0.88 (1)	2.39 (2)	3.115 (3)	140 (2)
N2—H2···O3	0.87 (1)	2.08 (1)	2.950 (2)	173 (2)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

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

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Katkova, M. A., Kurskii, Yu. A., Fukin, G. K., Averyushkin, A. S., Artamonov, A. N., Vitukhnovsky, A. G. & Bochkarev, M. N. (2005). Inorg. Chim. Acta, 358, 3625–3632. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar

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