{6,6'-Dimeth-oxy-2,2'-[(cyclo-hexane-1,2-di-yl)bis-(nitriliomethyl-idyne)]diphenolato}trinitratolanthanum(III) methanol monosolvate.

In the title mononuclear complex, [La(NO(3))(3)(C(22)H(26)N(2)O(4))]·CH(3)OH, the La(III) ion is coordinated by three bidentate nitrate counter-ions and one zwitterionic 6,6'-dimeth-oxy-2,2'-[(cyclo-hexane-1,2- di-yl)bis-(nitriliomethyl-idyne)]diphenolate ligand through two phenolate and two meth-oxy O atoms, while the protonated N atoms remain uncoordinated. H atoms located on the two N atoms are involved in intra-molecular hydrogen bonds with the deprotonated phenol O atoms, indicating that proton migration occurs during the lanthanum complexation.

Related literature

For the preparation of the ligand, see: Koner et al. (2005 ▶). For a related structure, see: Yan et al. (2009 ▶).

Experimental

Crystal data

[La(NO3)3(C22H26N2O4)]·CH4O

M = 739.43

Triclinic,

a = 9.7809 (4) Å

b = 12.8783 (5) Å

c = 13.0904 (5) Å

α = 79.374 (1)°

β = 68.743 (1)°

γ = 82.270 (1)°

V = 1506.22 (10) Å3

Z = 2

Mo Kα radiation

μ = 1.49 mm−1

T = 293 K

0.23 × 0.20 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.725, T max = 0.796

10874 measured reflections

7145 independent reflections

6526 reflections with I > 2σ(I)

R int = 0.010

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.092

S = 1.01

7145 reflections

389 parameters

38 restraints

H-atom parameters constrained

Δρmax = 0.97 e Å−3

Δρmin = −0.77 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810033453/vm2037sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810033453/vm2037Isup2.hkl

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

[La(NO3)3(C22H26N2O4)]·CH4O	Z = 2
Mr = 739.43	F(000) = 744
Triclinic, P1	Dx = 1.630 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.7809 (4) Å	Cell parameters from 6687 reflections
b = 12.8783 (5) Å	θ = 2.7–28.3°
c = 13.0904 (5) Å	µ = 1.49 mm−1
α = 79.374 (1)°	T = 293 K
β = 68.743 (1)°	Block, yellow
γ = 82.270 (1)°	0.23 × 0.20 × 0.16 mm
V = 1506.22 (10) Å3

Rigaku R-AXIS RAPID diffractometer	7145 independent reflections
Radiation source: fine-focus sealed tube	6526 reflections with I > 2σ(I)
graphite	Rint = 0.010
Detector resolution: 10.000 pixels mm-1	θmax = 28.3°, θmin = 2.7°
ω scan	h = −12→12
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→10
Tmin = 0.725, Tmax = 0.796	l = −17→17
10874 measured reflections

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.052P)2 + 1.3148P] where P = (Fo2 + 2Fc2)/3
7145 reflections	(Δ/σ)max = 0.011
389 parameters	Δρmax = 0.97 e Å−3
38 restraints	Δρmin = −0.77 e Å−3

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.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
La1	0.172411 (19)	0.227443 (12)	0.702241 (13)	0.04350 (7)
C1	0.2772 (3)	0.3560 (2)	0.4366 (2)	0.0404 (6)
C2	0.2940 (3)	0.2558 (2)	0.4018 (3)	0.0419 (6)
C3	0.3415 (3)	0.2462 (3)	0.2918 (3)	0.0482 (7)
H3A	0.3528	0.1797	0.2703	0.058*
C4	0.3735 (4)	0.3370 (3)	0.2111 (3)	0.0533 (8)
H4A	0.4072	0.3299	0.1364	0.064*
C5	0.3555 (4)	0.4351 (3)	0.2413 (3)	0.0483 (7)
H5A	0.3755	0.4946	0.1873	0.058*
C6	0.3065 (3)	0.4467 (2)	0.3548 (2)	0.0392 (6)
C7	0.2909 (3)	0.5487 (2)	0.3870 (2)	0.0414 (6)
H7A	0.3062	0.6077	0.3324	0.050*
C8	0.2394 (3)	0.6651 (2)	0.5270 (2)	0.0394 (6)
H8A	0.2616	0.7200	0.4618	0.047*
C9	0.3472 (4)	0.6692 (3)	0.5844 (3)	0.0532 (8)
H9A	0.4468	0.6553	0.5346	0.064*
H9B	0.3286	0.6153	0.6492	0.064*
C10	0.3307 (4)	0.7787 (3)	0.6190 (4)	0.0651 (10)
H10A	0.3964	0.7798	0.6593	0.078*
H10B	0.3593	0.8314	0.5532	0.078*
C11	0.1746 (4)	0.8071 (3)	0.6911 (3)	0.0562 (8)
H11A	0.1666	0.8794	0.7052	0.067*
H11B	0.1512	0.7610	0.7617	0.067*
C12	0.0645 (4)	0.7966 (2)	0.6370 (3)	0.0497 (7)
H12A	0.0780	0.8508	0.5727	0.060*
H12B	−0.0343	0.8086	0.6888	0.060*
C13	0.0799 (3)	0.6883 (2)	0.6012 (3)	0.0408 (6)
H13A	0.0162	0.6905	0.5578	0.049*
C14	−0.0445 (3)	0.6076 (2)	0.7970 (3)	0.0451 (6)
H14A	−0.0765	0.6743	0.8180	0.054*
C15	−0.0888 (3)	0.5169 (3)	0.8781 (3)	0.0450 (6)
C16	−0.1899 (4)	0.5304 (3)	0.9847 (3)	0.0554 (8)
H16A	−0.2188	0.5981	1.0038	0.066*
C17	−0.2449 (4)	0.4451 (3)	1.0591 (3)	0.0600 (9)
H17A	−0.3119	0.4548	1.1289	0.072*
C18	−0.2024 (4)	0.3425 (3)	1.0326 (3)	0.0544 (8)
H18A	−0.2434	0.2848	1.0838	0.065*
C19	−0.1002 (3)	0.3270 (3)	0.9312 (3)	0.0453 (6)
C20	−0.0405 (3)	0.4140 (2)	0.8507 (3)	0.0446 (6)
C21	−0.1055 (5)	0.1379 (3)	0.9726 (4)	0.0780 (13)
H21A	−0.1838	0.1597	1.0361	0.117*
H21B	−0.0289	0.0979	0.9957	0.117*
H21C	−0.1425	0.0948	0.9374	0.117*
C22	0.2813 (5)	0.0690 (3)	0.4624 (4)	0.0691 (11)
H22A	0.3126	0.0721	0.3835	0.104*
H22B	0.1898	0.0361	0.4966	0.104*
H22C	0.3544	0.0283	0.4891	0.104*
C23	0.2873 (10)	0.0899 (7)	0.0851 (7)	0.144 (3)
H29	0.3782	0.1074	0.0269	0.216*
H30	0.2505	0.0311	0.0699	0.216*
H31	0.3039	0.0710	0.1544	0.216*
N1	0.2565 (3)	0.56252 (19)	0.4883 (2)	0.0435 (5)
H1A	0.2423	0.5070	0.5376	0.052*
N2	0.0379 (3)	0.6013 (2)	0.6959 (2)	0.0444 (5)
H2A	0.0732	0.5387	0.6813	0.053*
N3	0.3925 (4)	0.2989 (3)	0.7882 (3)	0.0685 (9)
N4	0.3331 (4)	0.0205 (2)	0.7668 (3)	0.0568 (7)
N5	−0.0827 (4)	0.1433 (3)	0.6708 (3)	0.0700 (9)
O1	0.2366 (3)	0.36209 (17)	0.54227 (18)	0.0551 (6)
O2	0.2617 (3)	0.17450 (17)	0.4894 (2)	0.0548 (6)
O3	0.0536 (3)	0.39767 (17)	0.75338 (19)	0.0569 (6)
O4	−0.0473 (3)	0.23020 (17)	0.89550 (19)	0.0536 (6)
O5	0.2776 (4)	0.2560 (3)	0.8491 (2)	0.0817 (9)
O6	0.4763 (5)	0.3239 (4)	0.8270 (3)	0.1080 (14)
O7	0.4123 (4)	0.3163 (3)	0.6873 (3)	0.0898 (10)
O8	0.2108 (3)	0.0497 (2)	0.8293 (3)	0.0755 (8)
O9	0.4015 (4)	−0.0591 (3)	0.7944 (3)	0.0891 (10)
O10	0.3813 (4)	0.0756 (3)	0.6739 (3)	0.0857 (10)
O11	0.0096 (3)	0.0836 (2)	0.7053 (3)	0.0698 (7)
O12	−0.1833 (5)	0.1093 (4)	0.6569 (4)	0.1176 (16)
O13	−0.0650 (3)	0.2414 (2)	0.6515 (3)	0.0732 (8)
O14	0.1852 (7)	0.1766 (5)	0.0913 (5)	0.164 (2)
H14	0.2229	0.2291	0.0457	0.246*

	U11	U22	U33	U12	U13	U23
La1	0.05179 (11)	0.03034 (9)	0.03740 (10)	−0.00171 (7)	−0.00476 (7)	−0.00129 (6)
C1	0.0391 (13)	0.0398 (14)	0.0375 (14)	−0.0013 (11)	−0.0082 (11)	−0.0056 (11)
C2	0.0384 (13)	0.0390 (14)	0.0446 (15)	0.0008 (11)	−0.0106 (11)	−0.0073 (12)
C3	0.0464 (15)	0.0504 (16)	0.0498 (17)	0.0057 (13)	−0.0171 (13)	−0.0183 (14)
C4	0.0576 (18)	0.065 (2)	0.0374 (15)	−0.0006 (16)	−0.0155 (14)	−0.0125 (15)
C5	0.0493 (16)	0.0564 (18)	0.0371 (14)	−0.0064 (14)	−0.0143 (12)	−0.0012 (13)
C6	0.0370 (13)	0.0406 (14)	0.0367 (13)	−0.0040 (11)	−0.0099 (11)	−0.0028 (11)
C7	0.0413 (13)	0.0408 (15)	0.0377 (14)	−0.0076 (11)	−0.0101 (11)	0.0005 (11)
C8	0.0426 (14)	0.0314 (12)	0.0422 (14)	−0.0062 (11)	−0.0130 (11)	−0.0013 (11)
C9	0.0431 (15)	0.059 (2)	0.059 (2)	−0.0016 (14)	−0.0205 (14)	−0.0083 (16)
C10	0.059 (2)	0.064 (2)	0.085 (3)	−0.0135 (18)	−0.0314 (19)	−0.020 (2)
C11	0.068 (2)	0.0455 (17)	0.062 (2)	−0.0092 (15)	−0.0260 (17)	−0.0141 (15)
C12	0.0541 (17)	0.0343 (14)	0.0599 (19)	0.0000 (13)	−0.0207 (15)	−0.0055 (13)
C13	0.0413 (13)	0.0342 (13)	0.0475 (15)	−0.0023 (11)	−0.0177 (12)	−0.0033 (11)
C14	0.0431 (14)	0.0388 (14)	0.0508 (17)	0.0008 (12)	−0.0128 (13)	−0.0105 (13)
C15	0.0427 (14)	0.0448 (16)	0.0417 (15)	−0.0012 (12)	−0.0074 (12)	−0.0082 (12)
C16	0.0562 (18)	0.058 (2)	0.0438 (17)	0.0057 (15)	−0.0068 (14)	−0.0160 (15)
C17	0.0538 (18)	0.074 (2)	0.0383 (16)	0.0018 (17)	−0.0002 (14)	−0.0112 (16)
C18	0.0495 (16)	0.061 (2)	0.0397 (16)	−0.0070 (15)	−0.0043 (13)	0.0031 (14)
C19	0.0432 (14)	0.0440 (15)	0.0403 (15)	−0.0018 (12)	−0.0074 (12)	−0.0011 (12)
C20	0.0411 (14)	0.0410 (15)	0.0416 (15)	−0.0011 (12)	−0.0045 (12)	−0.0034 (12)
C21	0.089 (3)	0.0441 (19)	0.069 (3)	−0.0140 (19)	0.004 (2)	0.0125 (18)
C22	0.095 (3)	0.0348 (16)	0.068 (2)	−0.0024 (17)	−0.015 (2)	−0.0143 (16)
C23	0.162 (4)	0.146 (4)	0.137 (4)	−0.019 (3)	−0.061 (3)	−0.028 (3)
N1	0.0522 (13)	0.0331 (11)	0.0386 (12)	−0.0058 (10)	−0.0098 (10)	0.0001 (9)
N2	0.0450 (12)	0.0350 (12)	0.0454 (13)	−0.0035 (10)	−0.0069 (10)	−0.0048 (10)
N3	0.076 (2)	0.065 (2)	0.060 (2)	−0.0281 (17)	−0.0106 (16)	−0.0104 (16)
N4	0.0677 (18)	0.0447 (15)	0.0576 (17)	0.0093 (13)	−0.0234 (15)	−0.0126 (13)
N5	0.086 (2)	0.069 (2)	0.0593 (19)	−0.0215 (19)	−0.0333 (18)	0.0070 (16)
O1	0.0816 (16)	0.0351 (10)	0.0339 (10)	−0.0054 (10)	−0.0034 (10)	−0.0029 (8)
O2	0.0737 (15)	0.0334 (10)	0.0478 (12)	0.0012 (10)	−0.0102 (11)	−0.0093 (9)
O3	0.0665 (14)	0.0347 (11)	0.0437 (12)	−0.0009 (10)	0.0087 (10)	−0.0023 (9)
O4	0.0587 (13)	0.0373 (11)	0.0471 (12)	−0.0066 (10)	−0.0015 (10)	0.0048 (9)
O5	0.0813 (19)	0.109 (3)	0.0504 (15)	−0.0419 (19)	−0.0067 (14)	−0.0084 (16)
O6	0.104 (3)	0.144 (4)	0.089 (2)	−0.064 (3)	−0.028 (2)	−0.020 (2)
O7	0.087 (2)	0.117 (3)	0.0558 (17)	−0.048 (2)	−0.0052 (15)	0.0010 (17)
O8	0.0697 (17)	0.0567 (15)	0.0721 (18)	0.0137 (13)	−0.0071 (14)	0.0099 (13)
O9	0.094 (2)	0.073 (2)	0.085 (2)	0.0350 (17)	−0.0314 (18)	−0.0055 (17)
O10	0.084 (2)	0.082 (2)	0.0566 (16)	0.0293 (16)	−0.0019 (14)	−0.0002 (15)
O11	0.0806 (18)	0.0499 (14)	0.0781 (19)	−0.0116 (13)	−0.0315 (15)	0.0058 (13)
O12	0.138 (4)	0.110 (3)	0.139 (4)	−0.052 (3)	−0.093 (3)	0.021 (3)
O13	0.0836 (19)	0.0607 (17)	0.0798 (19)	−0.0035 (14)	−0.0426 (16)	0.0065 (14)
O14	0.181 (3)	0.165 (3)	0.146 (3)	0.001 (3)	−0.052 (2)	−0.044 (3)

La1—O1	2.406 (2)	C12—H12B	0.9700
La1—O3	2.428 (2)	C13—N2	1.484 (4)
La1—O5	2.586 (3)	C13—H13A	0.9800
La1—O11	2.587 (3)	C14—N2	1.287 (4)
La1—O10	2.604 (3)	C14—C15	1.423 (4)
La1—O13	2.613 (3)	C14—H14A	0.9300
La1—O8	2.639 (3)	C15—C20	1.411 (4)
La1—O4	2.663 (2)	C15—C16	1.414 (4)
La1—O7	2.676 (3)	C16—C17	1.352 (5)
La1—O2	2.787 (2)	C16—H16A	0.9300
La1—N5	3.034 (4)	C17—C18	1.398 (5)
La1—N4	3.048 (3)	C17—H17A	0.9300
C1—O1	1.308 (4)	C18—C19	1.372 (4)
C1—C6	1.415 (4)	C18—H18A	0.9300
C1—C2	1.416 (4)	C19—O4	1.381 (4)
C2—C3	1.367 (4)	C19—C20	1.415 (4)
C2—O2	1.376 (4)	C20—O3	1.308 (4)
C3—C4	1.409 (5)	C21—O4	1.441 (4)
C3—H3A	0.9300	C21—H21A	0.9600
C4—C5	1.364 (5)	C21—H21B	0.9600
C4—H4A	0.9300	C21—H21C	0.9600
C5—C6	1.415 (4)	C22—O2	1.437 (4)
C5—H5A	0.9300	C22—H22A	0.9600
C6—C7	1.425 (4)	C22—H22B	0.9600
C7—N1	1.285 (4)	C22—H22C	0.9600
C7—H7A	0.9300	C23—O14	1.388 (7)
C8—N1	1.468 (4)	C23—H29	0.9600
C8—C9	1.510 (4)	C23—H30	0.9600
C8—C13	1.533 (4)	C23—H31	0.9600
C8—H8A	0.9800	N1—H1A	0.8600
C9—C10	1.530 (5)	N2—H2A	0.8600
C9—H9A	0.9700	N3—O6	1.211 (5)
C9—H9B	0.9700	N3—O7	1.244 (5)
C10—C11	1.513 (5)	N3—O5	1.249 (4)
C10—H10A	0.9700	N4—O9	1.218 (4)
C10—H10B	0.9700	N4—O8	1.235 (4)
C11—C12	1.518 (5)	N4—O10	1.249 (4)
C11—H11A	0.9700	N5—O12	1.213 (5)
C11—H11B	0.9700	N5—O11	1.261 (5)
C12—C13	1.523 (4)	N5—O13	1.264 (5)
C12—H12A	0.9700	O14—H14	0.8416
O1—La1—O3	70.12 (7)	C11—C10—C9	111.9 (3)
O1—La1—O5	112.10 (10)	C11—C10—H10A	109.2
O3—La1—O5	77.05 (11)	C9—C10—H10A	109.2
O1—La1—O11	117.56 (9)	C11—C10—H10B	109.2
O3—La1—O11	118.33 (9)	C9—C10—H10B	109.2
O5—La1—O11	130.32 (10)	H10A—C10—H10B	107.9
O1—La1—O10	108.80 (9)	C10—C11—C12	111.8 (3)
O3—La1—O10	155.24 (12)	C10—C11—H11A	109.3
O5—La1—O10	80.89 (12)	C12—C11—H11A	109.3
O11—La1—O10	84.70 (11)	C10—C11—H11B	109.3
O1—La1—O13	80.42 (9)	C12—C11—H11B	109.3
O3—La1—O13	77.22 (10)	H11A—C11—H11B	107.9
O5—La1—O13	145.03 (11)	C11—C12—C13	112.8 (3)
O11—La1—O13	48.74 (9)	C11—C12—H12A	109.0
O10—La1—O13	127.48 (12)	C13—C12—H12A	109.0
O1—La1—O8	156.29 (9)	C11—C12—H12B	109.0
O3—La1—O8	129.69 (9)	C13—C12—H12B	109.0
O5—La1—O8	67.36 (12)	H12A—C12—H12B	107.8
O11—La1—O8	67.92 (10)	N2—C13—C12	113.2 (3)
O10—La1—O8	47.55 (9)	N2—C13—C8	109.2 (2)
O13—La1—O8	114.12 (10)	C12—C13—C8	109.2 (2)
O1—La1—O4	129.58 (7)	N2—C13—H13A	108.4
O3—La1—O4	61.66 (7)	C12—C13—H13A	108.4
O5—La1—O4	71.42 (9)	C8—C13—H13A	108.4
O11—La1—O4	76.31 (9)	N2—C14—C15	122.9 (3)
O10—La1—O4	121.04 (8)	N2—C14—H14A	118.5
O13—La1—O4	75.68 (9)	C15—C14—H14A	118.5
O8—La1—O4	73.68 (8)	C20—C15—C16	120.0 (3)
O1—La1—O7	70.19 (10)	C20—C15—C14	120.5 (3)
O3—La1—O7	82.23 (11)	C16—C15—C14	119.4 (3)
O5—La1—O7	47.34 (9)	C17—C16—C15	120.2 (3)
O11—La1—O7	159.25 (12)	C17—C16—H16A	119.9
O10—La1—O7	74.55 (13)	C15—C16—H16A	119.9
O13—La1—O7	148.50 (11)	C16—C17—C18	120.9 (3)
O8—La1—O7	97.37 (11)	C16—C17—H17A	119.5
O4—La1—O7	114.71 (9)	C18—C17—H17A	119.5
O1—La1—O2	59.31 (7)	C19—C18—C17	120.1 (3)
O3—La1—O2	124.53 (8)	C19—C18—H18A	120.0
O5—La1—O2	141.26 (9)	C17—C18—H18A	120.0
O11—La1—O2	71.75 (9)	C18—C19—O4	125.9 (3)
O10—La1—O2	68.96 (9)	C18—C19—C20	120.8 (3)
O13—La1—O2	73.57 (9)	O4—C19—C20	113.3 (3)
O8—La1—O2	105.25 (9)	O3—C20—C15	122.1 (3)
O4—La1—O2	145.47 (8)	O3—C20—C19	119.9 (3)
O7—La1—O2	99.75 (9)	C15—C20—C19	117.9 (3)
O1—La1—N5	99.24 (9)	O4—C21—H21A	109.5
O3—La1—N5	98.20 (10)	O4—C21—H21B	109.5
O5—La1—N5	143.84 (9)	H21A—C21—H21B	109.5
O11—La1—N5	24.29 (9)	O4—C21—H21C	109.5
O10—La1—N5	106.26 (12)	H21A—C21—H21C	109.5
O13—La1—N5	24.45 (9)	H21B—C21—H21C	109.5
O8—La1—N5	91.04 (10)	O2—C22—H22A	109.5
O4—La1—N5	74.87 (9)	O2—C22—H22B	109.5
O7—La1—N5	168.70 (10)	H22A—C22—H22B	109.5
O2—La1—N5	70.62 (9)	O2—C22—H22C	109.5
O1—La1—N4	132.60 (9)	H22A—C22—H22C	109.5
O3—La1—N4	146.68 (9)	H22B—C22—H22C	109.5
O5—La1—N4	71.57 (11)	O14—C23—H29	109.5
O11—La1—N4	76.25 (9)	O14—C23—H30	109.5
O10—La1—N4	23.91 (9)	H29—C23—H30	109.5
O13—La1—N4	124.87 (9)	O14—C23—H31	109.5
O8—La1—N4	23.70 (8)	H29—C23—H31	109.5
O4—La1—N4	97.16 (8)	H30—C23—H31	109.5
O7—La1—N4	84.69 (11)	C7—N1—C8	125.6 (2)
O2—La1—N4	87.83 (7)	C7—N1—H1A	117.2
N5—La1—N4	100.47 (10)	C8—N1—H1A	117.2
O1—C1—C6	122.1 (3)	C14—N2—C13	128.3 (3)
O1—C1—C2	119.6 (3)	C14—N2—H2A	115.8
C6—C1—C2	118.3 (3)	C13—N2—H2A	115.8
C3—C2—O2	126.5 (3)	O6—N3—O7	123.0 (4)
C3—C2—C1	121.1 (3)	O6—N3—O5	120.9 (4)
O2—C2—C1	112.4 (3)	O7—N3—O5	116.0 (3)
C2—C3—C4	120.0 (3)	O9—N4—O8	121.2 (3)
C2—C3—H3A	120.0	O9—N4—O10	122.1 (3)
C4—C3—H3A	120.0	O8—N4—O10	116.7 (3)
C5—C4—C3	120.7 (3)	O9—N4—La1	176.5 (3)
C5—C4—H4A	119.6	O8—N4—La1	59.21 (17)
C3—C4—H4A	119.6	O10—N4—La1	57.69 (17)
C4—C5—C6	120.1 (3)	O12—N5—O11	122.3 (4)
C4—C5—H5A	119.9	O12—N5—O13	121.3 (4)
C6—C5—H5A	119.9	O11—N5—O13	116.3 (3)
C1—C6—C5	119.8 (3)	O12—N5—La1	179.1 (4)
C1—C6—C7	119.7 (3)	O11—N5—La1	57.56 (19)
C5—C6—C7	120.5 (3)	O13—N5—La1	58.80 (19)
N1—C7—C6	122.8 (3)	C1—O1—La1	131.06 (19)
N1—C7—H7A	118.6	C2—O2—C22	116.7 (3)
C6—C7—H7A	118.6	C2—O2—La1	117.55 (17)
N1—C8—C9	111.1 (2)	C22—O2—La1	125.7 (2)
N1—C8—C13	110.4 (2)	C20—O3—La1	125.86 (19)
C9—C8—C13	112.1 (3)	C19—O4—C21	116.4 (3)
N1—C8—H8A	107.7	C19—O4—La1	117.93 (17)
C9—C8—H8A	107.7	C21—O4—La1	125.3 (2)
C13—C8—H8A	107.7	N3—O5—La1	100.4 (2)
C8—C9—C10	109.5 (3)	N3—O7—La1	96.1 (2)
C8—C9—H9A	109.8	N4—O8—La1	97.1 (2)
C10—C9—H9A	109.8	N4—O10—La1	98.4 (2)
C8—C9—H9B	109.8	N5—O11—La1	98.1 (2)
C10—C9—H9B	109.8	N5—O13—La1	96.8 (2)
H9A—C9—H9B	108.2	C23—O14—H14	111.0

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	1.86	2.562 (3)	137.
N2—H2A···O3	0.86	1.89	2.592 (3)	138.
O14—H14···O5i	0.84	2.40	2.981 (7)	127.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	1.86	2.562 (3)	137
N2—H2A⋯O3	0.86	1.89	2.592 (3)	138
O14—H14⋯O5i	0.84	2.40	2.981 (7)	127

Symmetry code: (i) .