Bis(μ-2-methyl-8-oxidoquinolin-1-ium-κ2O:O)bis­[(acetato-κ2O,O′)(2-methyl-8-oxidoquinolin-1-ium-κO)bis­(nitrato-κ2O,O′)lanthanum(III)]

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

doi:10.1107/S1600536809055743

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page m163

https://doi.org/10.1107/S1600536809055743

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Bis(μ-2-methyl-8-oxidoquinolin-1-ium-κ²O:O)bis[(acetato-κ²O,O′)(2-methyl-8-oxidoquinolin-1-ium-κO)bis(nitrato-κ²O,O′)lanthanum(III)]

Yousef Fazaeli,^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 17 December 2009; accepted 30 December 2009; online 16 January 2010)

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 ).

Experimental

Crystal data

[La₂(C₁₀H₉NO)₄(C₂H₃O₂)₂(NO₃)₄]
M_r = 1280.68
Monoclinic, P 2₁ /n
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 ) 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[F² > 2σ(F²)] = 0.032
wR(F²) = 0.112
S = 1.11
5769 reflections
358 parameters
58 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86 (1)	2.06 (1)	2.910 (5)	173 (5)
N2—H2⋯O4	0.86 (1)	2.20 (3)	2.926 (5)	143 (5)

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, 2010 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809055743/bt5149Isup2.hkl

checkCIF report

Related literature top

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).

Experimental top

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.

Structure description top

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).

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, 2010).

Figures top

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.

Bis(µ-2-methyl-8-oxidoquinolin-1-ium-κ²O:O)bis[(acetato- κ²O,O')(2-methyl-8-oxidoquinolin-1-ium- κO)bis(nitrato-κ²O,O')lanthanum(III)] top

Crystal data top

[La₂(C₁₀H₉NO)₄(C₂H₃O₂)₂(NO₃)₄]	F(000) = 1272
M_r = 1280.68	D_x = 1.690 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7894 reflections
a = 11.3686 (8) Å	θ = 2.2–27.8°
b = 17.5807 (12) Å	µ = 1.76 mm⁻¹
c = 13.0265 (10) Å	T = 295 K
β = 104.820 (1)°	Block, orange
V = 2517.0 (3) Å³	0.35 × 0.15 × 0.05 mm
Z = 2

Data collection top

Bruker SMART APEX diffractometer	5769 independent reflections
Radiation source: fine-focus sealed tube	4544 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.030
ω scans	θ_max = 27.5°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→12
T_min = 0.578, T_max = 0.917	k = −17→22
15685 measured reflections	l = −16→16

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)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0493P)² + 4.7409P] where P = (F_o² + 2F_c²)/3
5769 reflections	(Δ/σ)_max = 0.001
358 parameters	Δρ_max = 0.84 e Å⁻³
58 restraints	Δρ_min = −0.77 e Å⁻³

Crystal data top

[La₂(C₁₀H₉NO)₄(C₂H₃O₂)₂(NO₃)₄]	V = 2517.0 (3) Å³
M_r = 1280.68	Z = 2
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.3686 (8) Å	µ = 1.76 mm⁻¹
b = 17.5807 (12) Å	T = 295 K
c = 13.0265 (10) Å	0.35 × 0.15 × 0.05 mm
β = 104.820 (1)°

Data collection top

Bruker SMART APEX diffractometer	5769 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4544 reflections with I > 2σ(I)
T_min = 0.578, T_max = 0.917	R_int = 0.030
15685 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	58 restraints
wR(F²) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.84 e Å⁻³
5769 reflections	Δρ_min = −0.77 e Å⁻³
358 parameters

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
La1	0.59038 (2)	0.543193 (14)	0.648779 (18)	0.02973 (9)
O1	0.4836 (3)	0.53330 (19)	0.7782 (3)	0.0433 (8)
O2	0.5705 (3)	0.54741 (16)	0.4544 (2)	0.0298 (6)
O3	0.6618 (3)	0.4169 (2)	0.7427 (3)	0.0490 (9)
O4	0.7505 (3)	0.44741 (19)	0.6178 (3)	0.0466 (9)
O5	0.3958 (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)
O6	0.5573 (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)
O7	0.3882 (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)
O8	0.7936 (4)	0.6159 (2)	0.6401 (3)	0.0556 (10)
O9	0.7741 (4)	0.5927 (3)	0.7967 (3)	0.0620 (11)
O10	0.9344 (4)	0.6514 (3)	0.7766 (4)	0.0782 (14)
N1	0.5090 (4)	0.4012 (2)	0.8897 (3)	0.0398 (9)
N2	0.7810 (3)	0.4997 (2)	0.4128 (3)	0.0360 (9)
N3	0.4457 (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)
N4	0.8361 (4)	0.6214 (3)	0.7390 (4)	0.0470 (10)
C1	0.4074 (4)	0.5195 (3)	0.8361 (3)	0.0363 (10)
C2	0.3143 (5)	0.5680 (3)	0.8457 (4)	0.0474 (12)
H2A	0.3038	0.6140	0.8093	0.057*
C3	0.2355 (5)	0.5488 (4)	0.9092 (4)	0.0597 (16)
H3	0.1734	0.5822	0.9129	0.072*
C4	0.2472 (6)	0.4829 (4)	0.9653 (5)	0.0618 (16)
H4	0.1944	0.4721	1.0074	0.074*
C5	0.3394 (5)	0.4310 (3)	0.9597 (4)	0.0494 (13)
C6	0.4183 (5)	0.4505 (3)	0.8952 (4)	0.0384 (11)
C7	0.3617 (6)	0.3623 (4)	1.0154 (4)	0.0602 (16)
H7	0.3124	0.3482	1.0593	0.072*
C8	0.4531 (7)	0.3161 (3)	1.0068 (4)	0.0597 (17)
H8	0.4652	0.2703	1.0439	0.072*
C9	0.5307 (6)	0.3360 (3)	0.9425 (4)	0.0503 (13)
C10	0.6331 (7)	0.2879 (4)	0.9293 (5)	0.0681 (18)
H10A	0.6972	0.3198	0.9180	0.102*
H10B	0.6053	0.2549	0.8692	0.102*
H10C	0.6632	0.2579	0.9920	0.102*
C11	0.6280 (4)	0.5961 (3)	0.4055 (3)	0.0302 (9)
C12	0.5900 (4)	0.6680 (3)	0.3746 (4)	0.0396 (11)
H12	0.5207	0.6872	0.3908	0.048*
C13	0.6541 (5)	0.7138 (3)	0.3183 (4)	0.0509 (13)
H13	0.6259	0.7628	0.2994	0.061*
C14	0.7547 (5)	0.6897 (3)	0.2905 (4)	0.0512 (13)
H14	0.7932	0.7208	0.2513	0.061*
C15	0.7998 (4)	0.6162 (3)	0.3222 (4)	0.0410 (11)
C16	0.7377 (4)	0.5703 (3)	0.3809 (3)	0.0326 (9)
C17	0.9041 (5)	0.5839 (4)	0.2988 (5)	0.0527 (14)
H17	0.9478	0.6121	0.2607	0.063*
C18	0.9410 (5)	0.5128 (4)	0.3310 (5)	0.0586 (16)
H18	1.0094	0.4927	0.3141	0.070*
C19	0.8779 (4)	0.4684 (3)	0.3897 (4)	0.0443 (12)
C20	0.9120 (5)	0.3891 (3)	0.4264 (5)	0.0587 (15)
H20A	0.8942	0.3810	0.4937	0.088*
H20B	0.9974	0.3816	0.4337	0.088*
H20C	0.8664	0.3537	0.3754	0.088*
C21	0.7278 (4)	0.3996 (3)	0.6821 (4)	0.0436 (11)
C22	0.7752 (6)	0.3200 (4)	0.6835 (6)	0.074 (2)
H22A	0.8254	0.3085	0.7529	0.110*
H22B	0.8225	0.3155	0.6323	0.110*
H22C	0.7082	0.2851	0.6659	0.110*
H1	0.552 (4)	0.410 (3)	0.845 (3)	0.043 (14)*
H2	0.748 (4)	0.472 (2)	0.452 (3)	0.042 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
La1	0.03124 (15)	0.03346 (15)	0.02601 (13)	−0.00429 (11)	0.01007 (9)	−0.00058 (10)
O1	0.055 (2)	0.046 (2)	0.0370 (17)	−0.0002 (16)	0.0253 (16)	0.0023 (14)
O2	0.0299 (15)	0.0332 (16)	0.0284 (14)	−0.0021 (12)	0.0112 (12)	0.0018 (12)
O3	0.053 (2)	0.051 (2)	0.047 (2)	0.0087 (18)	0.0209 (17)	0.0113 (17)
O4	0.050 (2)	0.041 (2)	0.054 (2)	0.0048 (16)	0.0236 (17)	0.0087 (16)
O5	0.052 (3)	0.039 (3)	0.076 (3)	−0.006 (2)	0.011 (3)	−0.003 (3)
O6	0.073 (4)	0.033 (3)	0.127 (7)	−0.005 (3)	−0.013 (4)	−0.011 (3)
O7	0.116 (6)	0.073 (4)	0.119 (6)	0.053 (4)	0.026 (5)	−0.015 (4)
O8	0.061 (2)	0.065 (3)	0.044 (2)	−0.026 (2)	0.0209 (18)	−0.0052 (18)
O9	0.055 (2)	0.093 (3)	0.0380 (19)	−0.027 (2)	0.0114 (17)	0.002 (2)
O10	0.045 (2)	0.105 (4)	0.081 (3)	−0.033 (2)	0.010 (2)	−0.011 (3)
N1	0.053 (3)	0.039 (2)	0.0288 (19)	−0.0081 (19)	0.0135 (18)	−0.0017 (16)
N2	0.034 (2)	0.045 (2)	0.0330 (19)	−0.0017 (18)	0.0151 (16)	−0.0014 (17)
N3	0.062 (4)	0.055 (4)	0.053 (4)	0.019 (3)	0.019 (3)	−0.006 (3)
N4	0.039 (2)	0.051 (3)	0.050 (2)	−0.011 (2)	0.0106 (19)	−0.008 (2)
C1	0.043 (3)	0.041 (3)	0.026 (2)	−0.008 (2)	0.0112 (19)	−0.0061 (18)
C2	0.057 (3)	0.052 (3)	0.035 (2)	0.001 (3)	0.016 (2)	−0.002 (2)
C3	0.043 (3)	0.096 (5)	0.043 (3)	0.000 (3)	0.017 (2)	−0.010 (3)
C4	0.059 (4)	0.089 (5)	0.047 (3)	−0.020 (3)	0.030 (3)	−0.006 (3)
C5	0.054 (3)	0.065 (4)	0.031 (2)	−0.021 (3)	0.014 (2)	−0.006 (2)
C6	0.048 (3)	0.042 (3)	0.026 (2)	−0.013 (2)	0.0116 (19)	−0.0040 (19)
C7	0.083 (4)	0.064 (4)	0.042 (3)	−0.025 (3)	0.032 (3)	−0.002 (3)
C8	0.104 (5)	0.035 (3)	0.044 (3)	−0.033 (3)	0.026 (3)	−0.002 (2)
C9	0.077 (4)	0.039 (3)	0.035 (2)	−0.009 (3)	0.014 (2)	−0.002 (2)
C10	0.101 (5)	0.054 (4)	0.050 (3)	0.007 (4)	0.021 (3)	0.008 (3)
C11	0.027 (2)	0.039 (2)	0.0233 (18)	−0.0047 (18)	0.0037 (16)	0.0001 (17)
C12	0.038 (3)	0.038 (3)	0.044 (3)	0.000 (2)	0.012 (2)	0.002 (2)
C13	0.052 (3)	0.047 (3)	0.052 (3)	−0.011 (3)	0.010 (2)	0.003 (2)
C14	0.060 (3)	0.053 (3)	0.043 (3)	−0.014 (3)	0.017 (2)	0.013 (2)
C15	0.032 (2)	0.061 (3)	0.030 (2)	−0.014 (2)	0.0090 (18)	−0.006 (2)
C16	0.029 (2)	0.043 (3)	0.0243 (19)	−0.0067 (19)	0.0034 (16)	−0.0024 (18)
C17	0.045 (3)	0.065 (4)	0.054 (3)	−0.019 (3)	0.023 (2)	−0.007 (3)
C18	0.039 (3)	0.079 (4)	0.069 (4)	−0.007 (3)	0.035 (3)	−0.020 (3)
C19	0.033 (2)	0.057 (3)	0.042 (3)	0.001 (2)	0.008 (2)	−0.013 (2)
C20	0.050 (3)	0.064 (4)	0.062 (4)	0.012 (3)	0.013 (3)	−0.010 (3)
C21	0.035 (3)	0.045 (3)	0.049 (3)	0.004 (2)	0.008 (2)	0.011 (2)
C22	0.075 (4)	0.049 (4)	0.105 (6)	0.025 (3)	0.038 (4)	0.019 (4)

Geometric parameters (Å, º) top

La1—O1	2.322 (3)	C3—C4	1.358 (9)
La1—O2	2.485 (3)	C3—H3	0.9300
La1—O6'	2.49 (3)	C4—C5	1.405 (9)
La1—O2ⁱ	2.536 (3)	C4—H4	0.9300
La1—O3	2.564 (4)	C5—C7	1.399 (8)
La1—O4	2.586 (3)	C5—C6	1.418 (7)
La1—O9	2.603 (4)	C7—C8	1.346 (9)
La1—O5'	2.66 (3)	C7—H7	0.9300
La1—O6	2.635 (6)	C8—C9	1.408 (8)
La1—O5	2.663 (7)	C8—H8	0.9300
La1—O8	2.668 (4)	C9—C10	1.484 (9)
La1—C21	2.942 (5)	C10—H10A	0.9600
O1—C1	1.309 (5)	C10—H10B	0.9600
O2—C11	1.334 (5)	C10—H10C	0.9600
O2—La1ⁱ	2.536 (3)	C11—C12	1.363 (6)
O3—C21	1.257 (6)	C11—C16	1.438 (6)
O4—C21	1.260 (6)	C12—C13	1.410 (7)
O5—N3	1.239 (6)	C12—H12	0.9300
O5'—N3'	1.241 (7)	C13—C14	1.353 (8)
O6—N3	1.250 (6)	C13—H13	0.9300
O6'—N3'	1.241 (7)	C14—C15	1.412 (8)
O7—N3	1.233 (5)	C14—H14	0.9300
O7'—N3'	1.240 (7)	C15—C17	1.416 (7)
O8—N4	1.258 (6)	C15—C16	1.417 (6)
O9—N4	1.260 (5)	C17—C18	1.351 (9)
O10—N4	1.219 (5)	C17—H17	0.9300
N1—C9	1.327 (7)	C18—C19	1.410 (8)
N1—C6	1.362 (7)	C18—H18	0.9300
N1—H1	0.859 (10)	C19—C20	1.492 (8)
N2—C19	1.333 (6)	C20—H20A	0.9600
N2—C16	1.362 (6)	C20—H20B	0.9600
N2—H2	0.861 (10)	C20—H20C	0.9600
C1—C2	1.389 (7)	C21—C22	1.498 (8)
C1—C6	1.426 (7)	C22—H22A	0.9600
C2—C3	1.408 (8)	C22—H22B	0.9600
C2—H2A	0.9300	C22—H22C	0.9600

O1—La1—O2	144.47 (11)	O5'—N3'—O6'	119.9 (7)
O1—La1—O6'	75.4 (9)	O7'—N3'—La1	176.0 (13)
O2—La1—O6'	106.1 (9)	O5'—N3'—La1	63.9 (12)
O1—La1—O2ⁱ	84.12 (11)	O6'—N3'—La1	56.0 (12)
O2—La1—O2ⁱ	67.27 (11)	O10—N4—O8	121.1 (5)
O6'—La1—O2ⁱ	129.1 (6)	O10—N4—O9	121.9 (5)
O1—La1—O3	75.49 (11)	O8—N4—O9	117.0 (4)
O2—La1—O3	116.55 (11)	O10—N4—La1	178.6 (4)
O6'—La1—O3	136.3 (9)	O8—N4—La1	60.0 (2)
O2ⁱ—La1—O3	78.84 (11)	O9—N4—La1	57.0 (2)
O1—La1—O4	125.74 (11)	O1—C1—C2	124.7 (5)
O2—La1—O4	75.19 (11)	O1—C1—C6	119.3 (4)
O6'—La1—O4	142.2 (6)	C2—C1—C6	115.9 (4)
O2ⁱ—La1—O4	87.10 (11)	C1—C2—C3	121.3 (5)
O3—La1—O4	50.30 (11)	C1—C2—H2A	119.4
O1—La1—O9	87.53 (12)	C3—C2—H2A	119.4
O2—La1—O9	126.22 (10)	C4—C3—C2	122.1 (6)
O6'—La1—O9	66.1 (6)	C4—C3—H3	118.9
O2ⁱ—La1—O9	159.37 (12)	C2—C3—H3	118.9
O3—La1—O9	80.82 (13)	C3—C4—C5	119.9 (5)
O4—La1—O9	82.54 (14)	C3—C4—H4	120.1
O1—La1—O5'	82.3 (8)	C5—C4—H4	120.1
O2—La1—O5'	73.8 (6)	C7—C5—C4	124.9 (5)
O6'—La1—O5'	49.1 (5)	C7—C5—C6	117.3 (6)
O2ⁱ—La1—O5'	82.6 (7)	C4—C5—C6	117.9 (5)
O3—La1—O5'	152.3 (8)	N1—C6—C5	118.7 (5)
O4—La1—O5'	148.9 (7)	N1—C6—C1	118.4 (4)
O9—La1—O5'	115.0 (6)	C5—C6—C1	123.0 (5)
O1—La1—O6	87.0 (3)	C8—C7—C5	121.2 (5)
O2—La1—O6	91.4 (3)	C8—C7—H7	119.4
O6'—La1—O6	14.7 (7)	C5—C7—H7	119.4
O2ⁱ—La1—O6	123.18 (19)	C7—C8—C9	121.0 (5)
O3—La1—O6	150.6 (3)	C7—C8—H8	119.5
O4—La1—O6	139.4 (2)	C9—C8—H8	119.5
O9—La1—O6	75.0 (2)	N1—C9—C8	117.4 (6)
O5'—La1—O6	40.6 (6)	N1—C9—C10	118.7 (5)
O1—La1—O5	75.8 (2)	C8—C9—C10	123.9 (5)
O2—La1—O5	77.14 (18)	C9—C10—H10A	109.5
O6'—La1—O5	54.1 (6)	C9—C10—H10B	109.5
O2ⁱ—La1—O5	75.98 (17)	H10A—C10—H10B	109.5
O3—La1—O5	143.3 (2)	C9—C10—H10C	109.5
O4—La1—O5	151.49 (17)	H10A—C10—H10C	109.5
O9—La1—O5	120.07 (17)	H10B—C10—H10C	109.5
O5'—La1—O5	9.0 (7)	O2—C11—C12	125.4 (4)
O6—La1—O5	47.51 (16)	O2—C11—C16	117.6 (4)
O1—La1—O8	133.29 (12)	C12—C11—C16	117.0 (4)
O2—La1—O8	78.27 (10)	C11—C12—C13	121.1 (5)
O6'—La1—O8	73.6 (7)	C11—C12—H12	119.5
O2ⁱ—La1—O8	142.52 (10)	C13—C12—H12	119.5
O3—La1—O8	105.23 (13)	C14—C13—C12	123.0 (5)
O4—La1—O8	69.72 (12)	C14—C13—H13	118.5
O9—La1—O8	48.04 (11)	C12—C13—H13	118.5
O5'—La1—O8	102.1 (8)	C13—C14—C15	118.5 (5)
O6—La1—O8	70.12 (18)	C13—C14—H14	120.8
O5—La1—O8	111.0 (2)	C15—C14—H14	120.8
O1—La1—C21	100.66 (13)	C14—C15—C17	124.4 (5)
O2—La1—C21	94.73 (12)	C14—C15—C16	119.0 (5)
O6'—La1—C21	149.1 (7)	C17—C15—C16	116.6 (5)
O2ⁱ—La1—C21	79.82 (12)	N2—C16—C15	119.6 (4)
O3—La1—C21	25.22 (12)	N2—C16—C11	119.1 (4)
O4—La1—C21	25.30 (12)	C15—C16—C11	121.4 (4)
O9—La1—C21	83.26 (15)	C18—C17—C15	121.0 (5)
O5'—La1—C21	161.7 (6)	C18—C17—H17	119.5
O6—La1—C21	156.65 (18)	C15—C17—H17	119.5
O5—La1—C21	155.77 (18)	C17—C18—C19	121.3 (5)
O8—La1—C21	89.09 (13)	C17—C18—H18	119.4
C1—O1—La1	168.0 (3)	C19—C18—H18	119.4
C11—O2—La1	125.3 (2)	N2—C19—C18	117.3 (5)
C11—O2—La1ⁱ	121.7 (2)	N2—C19—C20	118.3 (5)
La1—O2—La1ⁱ	112.73 (10)	C18—C19—C20	124.3 (5)
C21—O3—La1	94.4 (3)	C19—C20—H20A	109.5
C21—O4—La1	93.3 (3)	C19—C20—H20B	109.5
N3—O5—La1	96.5 (4)	H20A—C20—H20B	109.5
N3'—O5'—La1	91.4 (12)	C19—C20—H20C	109.5
N3—O6—La1	97.6 (4)	H20A—C20—H20C	109.5
N3'—O6'—La1	99.6 (13)	H20B—C20—H20C	109.5
N4—O8—La1	95.9 (3)	O3—C21—O4	120.8 (5)
N4—O9—La1	99.0 (3)	O3—C21—C22	119.3 (5)
C9—N1—C6	124.4 (4)	O4—C21—C22	119.8 (5)
C9—N1—H1	116 (4)	O3—C21—La1	60.3 (3)
C6—N1—H1	119 (4)	O4—C21—La1	61.4 (3)
C19—N2—C16	124.2 (4)	C22—C21—La1	168.3 (4)
C19—N2—H2	114 (3)	C21—C22—H22A	109.5
C16—N2—H2	122 (3)	C21—C22—H22B	109.5
O7—N3—O5	121.7 (5)	H22A—C22—H22B	109.5
O7—N3—O6	120.1 (5)	C21—C22—H22C	109.5
O5—N3—O6	118.1 (5)	H22A—C22—H22C	109.5
O7'—N3'—O5'	120.2 (7)	H22B—C22—H22C	109.5
O7'—N3'—O6'	120.0 (7)

O2—La1—O1—C1	29.7 (17)	La1—O6—N3—O5	−4.4 (5)
O6'—La1—O1—C1	127.1 (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—C1	77.4 (17)	O2—La1—N3'—O5'	48.0 (18)
O6—La1—O1—C1	117.9 (16)	O6'—La1—N3'—O5'	179.9 (18)
O5—La1—O1—C1	71.1 (16)	O2ⁱ—La1—N3'—O5'	−18.3 (19)
O8—La1—O1—C1	176.7 (16)	O3—La1—N3'—O5'	−115 (2)
C21—La1—O1—C1	−84.3 (16)	O4—La1—N3'—O5'	101.2 (18)
O1—La1—O2—C11	135.0 (3)	O9—La1—N3'—O5'	174.2 (18)
O6'—La1—O2—C11	47.8 (7)	O6—La1—N3'—O5'	142 (2)
O2ⁱ—La1—O2—C11	174.0 (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—C11	85.4 (8)	O5'—La1—N3'—O6'	−179.9 (18)
O6—La1—O2—C11	48.3 (3)	O5—La1—N3'—O6'	164.5 (19)
O5—La1—O2—C11	94.0 (4)	La1—O8—N4—O10	179.0 (5)
O8—La1—O2—C11	−21.1 (3)	La1—O8—N4—O9	0.9 (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—La1ⁱ	0.0	O2—La1—N4—O8	2.7 (3)
O3—La1—O2—La1ⁱ	63.64 (15)	O6'—La1—N4—O8	−99.8 (11)
O4—La1—O2—La1ⁱ	93.10 (13)	O2ⁱ—La1—N4—O8	56.4 (5)
O9—La1—O2—La1ⁱ	161.98 (14)	O3—La1—N4—O8	120.8 (3)
O5'—La1—O2—La1ⁱ	−88.6 (8)	O4—La1—N4—O8	73.5 (3)
O6—La1—O2—La1ⁱ	−125.68 (16)	O9—La1—N4—O8	179.0 (5)
O5—La1—O2—La1ⁱ	−80.0 (2)	O5'—La1—N4—O8	−74.3 (8)
O8—La1—O2—La1ⁱ	164.96 (15)	O6—La1—N4—O8	−84.4 (5)
C21—La1—O2—La1ⁱ	76.88 (14)	O5—La1—N4—O8	−79.1 (4)
O1—La1—O3—C21	176.5 (3)	C21—La1—N4—O8	96.7 (3)
O2—La1—O3—C21	32.4 (3)	O1—La1—N4—O9	17.6 (4)
O6'—La1—O3—C21	−133.9 (10)	O2—La1—N4—O9	−176.3 (3)
O2ⁱ—La1—O3—C21	89.8 (3)	O6'—La1—N4—O9	81.2 (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—C21	138.6 (12)	O4—La1—N4—O9	−105.5 (3)
O6—La1—O3—C21	−128.3 (4)	O5'—La1—N4—O9	106.7 (8)
O5—La1—O3—C21	137.1 (3)	O6—La1—N4—O9	96.6 (5)
O8—La1—O3—C21	−51.9 (3)	O5—La1—N4—O9	101.9 (4)
O1—La1—O4—C21	8.5 (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—C21	123.4 (15)	La1—O1—C1—C2	−94.4 (16)
O2ⁱ—La1—O4—C21	−72.1 (3)	La1—O1—C1—C6	85.9 (16)
O3—La1—O4—C21	5.8 (3)	O1—C1—C2—C3	179.6 (5)
O9—La1—O4—C21	90.0 (3)	C6—C1—C2—C3	−0.7 (7)
O5'—La1—O4—C21	−142.6 (15)	C1—C2—C3—C4	0.9 (9)
O6—La1—O4—C21	146.3 (5)	C2—C3—C4—C5	−0.9 (9)
O5—La1—O4—C21	−125.1 (5)	C3—C4—C5—C7	178.6 (6)
O8—La1—O4—C21	137.9 (3)	C3—C4—C5—C6	0.6 (8)
O1—La1—O5—N3	96.7 (6)	C9—N1—C6—C5	−1.3 (7)
O2—La1—O5—N3	−106.5 (6)	C9—N1—C6—C1	178.5 (4)
O6'—La1—O5—N3	14.5 (10)	C7—C5—C6—N1	1.1 (7)
O2ⁱ—La1—O5—N3	−176.0 (6)	C4—C5—C6—N1	179.3 (5)
O3—La1—O5—N3	136.0 (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—N3	18.1 (7)	O1—C1—C6—N1	0.4 (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—C5	0.5 (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—C9	1.0 (9)
O6'—La1—O5'—N3'	−0.1 (10)	C6—N1—C9—C8	1.2 (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—C10	180.0 (6)
O9—La1—O5'—N3'	−6 (2)	La1—O2—C11—C12	−84.2 (5)
O6—La1—O5'—N3'	−17.1 (10)	La1ⁱ—O2—C11—C12	89.2 (5)
O5—La1—O5'—N3'	120 (5)	La1—O2—C11—C16	97.3 (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—C13	1.8 (7)
O2—La1—O6—N3	73.5 (6)	C11—C12—C13—C14	0.9 (8)
O6'—La1—O6—N3	−108 (3)	C12—C13—C14—C15	−2.1 (8)
O2ⁱ—La1—O6—N3	10.0 (8)	C13—C14—C15—C17	−179.9 (5)
O3—La1—O6—N3	−123.7 (4)	C13—C14—C15—C16	0.6 (7)
O4—La1—O6—N3	142.1 (3)	C19—N2—C16—C15	−2.2 (7)
O9—La1—O6—N3	−159.2 (6)	C19—N2—C16—C11	176.3 (4)
O5'—La1—O6—N3	10.7 (11)	C14—C15—C16—N2	−179.4 (4)
O5—La1—O6—N3	2.5 (3)	C17—C15—C16—N2	1.0 (6)
O8—La1—O6—N3	150.5 (7)	C14—C15—C16—C11	2.1 (6)
C21—La1—O6—N3	178.9 (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—N2	178.2 (4)
O2ⁱ—La1—O6'—N3'	−23 (2)	O2—C11—C16—C15	175.3 (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—C18	0.3 (7)
O5'—La1—O6'—N3'	0.1 (10)	C15—C17—C18—C19	−0.5 (9)
O6—La1—O6'—N3'	49 (2)	C16—N2—C19—C18	2.0 (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—C20	179.0 (5)
O1—La1—O8—N4	21.5 (4)	La1—O3—C21—O4	10.7 (5)
O2—La1—O8—N4	−177.3 (3)	La1—O3—C21—C22	−166.5 (5)
O6'—La1—O8—N4	71.8 (9)	La1—O4—C21—O3	−10.6 (5)
O2ⁱ—La1—O8—N4	−154.2 (3)	La1—O4—C21—C22	166.6 (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—O3	75.9 (18)
O5'—La1—O8—N4	112.3 (7)	O2ⁱ—La1—C21—O3	−85.4 (3)
O6—La1—O8—N4	86.9 (5)	O4—La1—C21—O3	169.6 (5)
O5—La1—O8—N4	111.6 (3)	O9—La1—C21—O3	82.8 (3)
C21—La1—O8—N4	−82.3 (3)	O5'—La1—C21—O3	−101 (3)
O1—La1—O9—N4	−163.5 (3)	O6—La1—C21—O3	104.1 (9)
O2—La1—O9—N4	4.5 (4)	O5—La1—C21—O3	−82.4 (6)
O6'—La1—O9—N4	−88.4 (11)	O8—La1—C21—O3	130.6 (3)
O2ⁱ—La1—O9—N4	130.4 (3)	O1—La1—C21—O4	−173.0 (3)
O3—La1—O9—N4	120.8 (3)	O2—La1—C21—O4	39.2 (3)
O4—La1—O9—N4	69.9 (3)	O6'—La1—C21—O4	−93.6 (18)
O5'—La1—O9—N4	−83.2 (9)	O2ⁱ—La1—C21—O4	105.0 (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—N4	0.6 (3)	O5'—La1—C21—O4	89 (3)
C21—La1—O9—N4	95.4 (3)	O6—La1—C21—O4	−65.5 (9)
La1—O5—N3—O7	−175.8 (4)	O5—La1—C21—O4	108.1 (6)
La1—O5—N3—O6	4.4 (5)	O8—La1—C21—O4	−39.0 (3)
La1—O6—N3—O7	175.7 (4)

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···O3	0.86 (1)	2.06 (1)	2.910 (5)	173 (5)
N2—H2···O4	0.86 (1)	2.20 (3)	2.926 (5)	143 (5)

Experimental details

Crystal data
Chemical formula	[La₂(C₁₀H₉NO)₄(C₂H₃O₂)₂(NO₃)₄]
M_r	1280.68
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	11.3686 (8), 17.5807 (12), 13.0265 (10)
β (°)	104.820 (1)
V (Å³)	2517.0 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.76
Crystal size (mm)	0.35 × 0.15 × 0.05

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.578, 0.917
No. of measured, independent and observed [I > 2σ(I)] reflections	15685, 5769, 4544
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.112, 1.11
No. of reflections	5769
No. of parameters	358
No. of restraints	58
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.77

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86 (1)	2.06 (1)	2.910 (5)	173 (5)
N2—H2···O4	0.86 (1)	2.20 (3)	2.926 (5)	143 (5)

Acknowledgements

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

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