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)]

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.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.008 Å
• Disorder in main residue
• R factor = 0.032
• wR factor = 0.112
• Data-to-parameter ratio = 16.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.46 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    O5     --  N3      ..       5.72 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  La1    --  O9      ..       5.28 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O8
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        La1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        N3'
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      47.00 A   3 
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.600         10
PLAT731_ALERT_1_C Bond    Calc     0.87(4), Rep   0.859(10) ......       4.00 su-Ra
              N1   -H1      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     0.86(4), Rep   0.861(10) ......       4.00 su-Ra
              N2   -H2      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.87(4), Rep   0.860(10) ......       4.00 su-Ra
              N1   -H1      1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.86(4), Rep   0.860(10) ......       4.00 su-Ra
              N2   -H2      1.555   1.555
PLAT736_ALERT_1_C H...A   Calc     2.05(4), Rep   2.060(10) ......       4.00 su-Ra
              H1   -O3      1.555   1.555

Alert level G
PLAT301_ALERT_3_G Note: Main Residue  Disorder ...................      10.00 Perc.
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         58
PLAT128_ALERT_4_G Non-standard setting of Space-group P21/c   ....      P21/n

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  16 ALERT level C = Check and explain
   3 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
  10 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

---

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).

S1. 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.

S2. 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.

Structure description

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

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

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)]

Crystal data

[La2(C10H9NO)4(C2H3O2)2(NO3)4]	F(000) = 1272
Mr = 1280.68	Dx = 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) Å^3	0.35 × 0.15 × 0.05 mm
Z = 2

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0493P)^2 + 4.7409P] where P = (Fo^2 + 2Fc^2)/3
5769 reflections	(Δ/σ)max = 0.001
358 parameters	Δρmax = 0.84 e Å^−3
58 restraints	Δρmin = −0.77 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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—O2^i	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—La1^i	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—O2^i	84.12 (11)	O6'—N3'—La1	56.0 (12)
O2—La1—O2^i	67.27 (11)	O10—N4—O8	121.1 (5)
O6'—La1—O2^i	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)
O2^i—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)
O2^i—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
O2^i—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)
O2^i—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
O2^i—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
O2^i—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
O2^i—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)
O2^i—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—La1^i	121.7 (2)	N2—C19—C20	118.3 (5)
La1—O2—La1^i	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)
O2^i—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)	O2^i—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)
O2^i—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—La1^i	−38.9 (2)	La1—O9—N4—O8	−1.0 (5)
O6'—La1—O2—La1^i	−126.2 (7)	O1—La1—N4—O8	−163.4 (3)
O2^i—La1—O2—La1^i	0.0	O2—La1—N4—O8	2.7 (3)
O3—La1—O2—La1^i	63.64 (15)	O6'—La1—N4—O8	−99.8 (11)
O4—La1—O2—La1^i	93.10 (13)	O2^i—La1—N4—O8	56.4 (5)
O9—La1—O2—La1^i	161.98 (14)	O3—La1—N4—O8	120.8 (3)
O5'—La1—O2—La1^i	−88.6 (8)	O4—La1—N4—O8	73.5 (3)
O6—La1—O2—La1^i	−125.68 (16)	O9—La1—N4—O8	179.0 (5)
O5—La1—O2—La1^i	−80.0 (2)	O5'—La1—N4—O8	−74.3 (8)
O8—La1—O2—La1^i	164.96 (15)	O6—La1—N4—O8	−84.4 (5)
C21—La1—O2—La1^i	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)
O2^i—La1—O3—C21	89.8 (3)	O6'—La1—N4—O9	81.2 (11)
O4—La1—O3—C21	−5.8 (3)	O2^i—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)
O2^i—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)
O2^i—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)
O2^i—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)	La1^i—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)	La1^i—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)
O2^i—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)
O2^i—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)
O2^i—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)	O2^i—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)
O2^i—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)	O2^i—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)

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)