Two novel lanthanide(III) organic frameworks based on a biphenyl­tetra­carboxyl­ate ligand: synthesis, structure and magnetic and luminescence properties

Two new two-dimensional lanthanide coordination polymers, namely poly[[tetra-μ₂-acetato-tetra­aqua­bis­(μ₄-biphenyl-3,3′,5,5′-tetra­carboxyl­ato)tetra­kis­(di­methyl­acetamide)­tetra­terbium(III)] penta­hydrate], {[Tb₄(C₁₆H₆O₈)₂(C₂H₃O₂)₄(C₄H₉NO)₄(H₂O)₄]·5H₂O}_n, (1), and poly[[tetra-μ₂-acetato-tetra­aqua­bis­(μ₅-biphenyl-3,3′,5,5′-tetra­carboxyl­ato)tetra­kis­(di­methyl­acetamide)­tetra­europium(III)] tetra­hydrate], {[Eu₄(C₁₆H₆O₈)₂(C₂H₃O₂)₄(C₄H₉NO)₄(H₂O)₄]·4H₂O}_n, (2), have been synthesized from biphenyl-3,3′,5,5′-tetra­carb­oxy­lic acid (H₄bpt) and Ln(NO₃)₃·6H₂O (Ln = Tb and Eu) under solvothermal conditions. Single-crystal X-ray structure analysis shows that the two compounds are isostructural and crystallize in the monoclinic P2₁/n space group. The crystal structures are constructed from bpt⁴⁻ ligands (as linkers) and {Ln₂(μ₂-CH₃COO)₂} building units (as nodes), which topological analysis shows to be a (4,6)-connected network with sql topology. Compounds (1) and (2) have been characterized by elemental analysis, IR spectroscopy, powder X-ray diffraction (PXRD), thermogravimetric analysis (TGA) and fluorescence analysis in the solid state. In addition, a magnetic investigation shows the presence of anti­ferromagnetic inter­actions in compound (1).

Computing details

For both structures, data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS2015 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2015 (Sheldrick, 2015b); molecular graphics: Please provide; software used to prepare material for publication: SHELXL2015 (Sheldrick, 2015b).

Poly[[tetraaquatetra-µ₂-acetato-bis(µ₄-biphenyl-3,3',5,5'-tetracarboxylato)tetrakis(dimethylacetamide)tetraterbium(III)] pentahydrate] (140901b)

Crystal data

[Tb4(C16H6O8)2(C2H3O2)4(C4H9NO)4(H2O)4]·5H2O	F(000) = 940
Mr = 2026.53	Dx = 1.726 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.3676 (7) Å	Cell parameters from 2165 reflections
b = 17.6232 (14) Å	θ = 2.9–25.9°
c = 11.3172 (9) Å	µ = 3.83 mm^−1
β = 94.351 (2)°	T = 298 K
V = 1862.9 (3) Å^3	Bloc, colorless
Z = 1	0.15 × 0.13 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer	2200 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.072
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θmax = 25.0°, θmin = 2.9°
Tmin = 0.597, Tmax = 0.656	h = −10→11
8955 measured reflections	k = −20→20
3162 independent reflections	l = −11→13

Refinement

Refinement on F^2	448 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.060	H-atom parameters constrained
wR(F^2) = 0.155	w = 1/[σ^2(Fo^2) + (0.0882P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.01	(Δ/σ)max = 0.001
3162 reflections	Δρmax = 1.50 e Å^−3
221 parameters	Δρmin = −1.58 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Tb1	0.48343 (5)	0.10111 (2)	0.06839 (4)	0.0370 (2)
C1	0.822 (2)	0.0588 (10)	−0.1747 (16)	0.098 (4)
H1A	0.905310	0.084451	−0.139851	0.147*
H1B	0.799926	0.077386	−0.253716	0.147*
H1C	0.840486	0.005255	−0.177338	0.147*
C2	0.6939 (15)	0.0737 (7)	−0.0994 (12)	0.061 (2)
C3	0.5268 (15)	0.2595 (6)	0.1013 (11)	0.0549 (17)
C4	0.5558 (13)	0.3410 (6)	0.1141 (10)	0.0487 (17)
C5	0.4995 (14)	0.3955 (6)	0.0340 (11)	0.0509 (18)
H5	0.437069	0.379567	−0.028934	0.061*
C6	0.5315 (13)	0.4707 (6)	0.0433 (10)	0.0490 (19)
C7	0.6304 (12)	0.4920 (5)	0.1372 (9)	0.0463 (19)
H7	0.656462	0.542738	0.144899	0.056*
C8	0.6904 (13)	0.4403 (5)	0.2188 (10)	0.0490 (18)
C9	0.7897 (13)	0.4650 (5)	0.3233 (10)	0.048 (2)
C10	0.6527 (13)	0.3644 (6)	0.2052 (10)	0.0487 (17)
H10	0.693296	0.328676	0.258167	0.058*
C11	0.221 (2)	0.1696 (9)	0.2219 (15)	0.081 (2)
C12	0.262 (2)	0.1960 (12)	0.3475 (18)	0.118 (4)
H12A	0.185238	0.225246	0.375752	0.178*
H12B	0.346764	0.226839	0.348357	0.178*
H12C	0.280473	0.152733	0.397841	0.178*
C13	0.025 (2)	0.1418 (13)	0.0616 (17)	0.111 (4)
H13A	0.024026	0.175873	−0.004683	0.167*
H13B	−0.070295	0.123833	0.070392	0.167*
H13C	0.086455	0.099546	0.048289	0.167*
C14	−0.038 (2)	0.2328 (12)	0.2245 (18)	0.116 (4)
H14A	−0.017134	0.248015	0.305385	0.174*
H14B	−0.123468	0.202404	0.218450	0.174*
H14C	−0.052455	0.277035	0.175511	0.174*
O8	0.6689 (7)	0.0340 (4)	0.1736 (6)	0.0394 (11)
N1	0.085 (2)	0.1871 (10)	0.1837 (18)	0.128 (5)
O1	0.6106 (9)	0.0205 (4)	−0.0793 (7)	0.0507 (16)
O2	0.6799 (10)	0.1354 (5)	−0.0524 (7)	0.0604 (16)
O3	0.4373 (10)	0.2369 (4)	0.0145 (7)	0.0597 (15)
O4	0.5873 (9)	0.2110 (4)	0.1704 (7)	0.0533 (14)
O5	0.2821 (12)	0.1275 (6)	0.1533 (9)	0.083 (2)
O6	0.4559 (15)	0.0818 (7)	0.2856 (9)	0.100 (3)
O7	0.3366 (10)	0.0867 (4)	−0.1050 (8)	0.0585 (17)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Tb1	0.0467 (4)	0.0168 (3)	0.0444 (3)	0.0029 (2)	−0.0169 (2)	−0.0035 (2)
C1	0.102 (9)	0.091 (8)	0.103 (9)	−0.019 (8)	0.023 (8)	−0.002 (8)
C2	0.073 (5)	0.046 (4)	0.065 (4)	−0.010 (4)	0.006 (4)	−0.004 (4)
C3	0.073 (3)	0.033 (3)	0.055 (3)	0.000 (3)	−0.016 (3)	−0.007 (3)
C4	0.067 (4)	0.024 (3)	0.051 (3)	0.002 (3)	−0.019 (3)	−0.001 (3)
C5	0.069 (4)	0.028 (3)	0.052 (3)	0.000 (3)	−0.022 (3)	−0.001 (3)
C6	0.069 (4)	0.023 (3)	0.052 (4)	0.003 (3)	−0.020 (4)	−0.001 (3)
C7	0.065 (4)	0.024 (3)	0.046 (4)	−0.002 (3)	−0.024 (3)	0.002 (3)
C8	0.064 (4)	0.026 (3)	0.053 (4)	−0.001 (3)	−0.021 (3)	−0.004 (3)
C9	0.065 (5)	0.024 (4)	0.050 (4)	0.001 (4)	−0.025 (4)	−0.001 (4)
C10	0.069 (4)	0.026 (3)	0.048 (3)	0.002 (3)	−0.020 (3)	0.000 (3)
C11	0.095 (5)	0.064 (4)	0.080 (5)	0.003 (4)	−0.004 (4)	−0.012 (4)
C12	0.129 (9)	0.114 (9)	0.111 (9)	0.013 (8)	0.005 (8)	−0.020 (8)
C13	0.116 (9)	0.103 (9)	0.115 (9)	0.005 (8)	0.010 (8)	0.000 (8)
C14	0.124 (9)	0.115 (9)	0.109 (9)	0.008 (8)	0.009 (8)	−0.015 (8)
O8	0.0396 (13)	0.0377 (13)	0.0400 (14)	0.0038 (9)	−0.0037 (9)	0.0020 (9)
N1	0.105 (12)	0.124 (14)	0.151 (14)	0.002 (10)	−0.020 (11)	0.038 (10)
O1	0.065 (4)	0.029 (3)	0.057 (4)	−0.006 (3)	−0.001 (3)	0.000 (3)
O2	0.080 (4)	0.040 (3)	0.061 (3)	−0.011 (3)	0.003 (3)	−0.007 (3)
O3	0.079 (3)	0.035 (3)	0.062 (3)	0.001 (3)	−0.021 (3)	−0.007 (3)
O4	0.073 (3)	0.030 (3)	0.054 (3)	0.003 (3)	−0.017 (3)	−0.004 (2)
O5	0.094 (4)	0.066 (4)	0.088 (4)	0.005 (4)	0.007 (4)	−0.013 (3)
O6	0.136 (7)	0.115 (6)	0.049 (2)	0.001 (6)	0.000 (5)	0.000 (5)
O7	0.077 (4)	0.037 (3)	0.059 (4)	0.003 (3)	−0.018 (3)	−0.009 (3)

Geometric parameters (Å, º)

Tb1—O5	2.229 (11)	C6—C7	1.407 (15)
Tb1—O1^i	2.324 (7)	C6—C6^ii	1.51 (2)
Tb1—O7	2.323 (8)	C7—C8	1.385 (14)
Tb1—O8	2.350 (7)	C7—H7	0.9300
Tb1—O4	2.421 (7)	C8—C10	1.390 (15)
Tb1—O2	2.451 (9)	C8—C9	1.512 (15)
Tb1—O3	2.499 (7)	C9—O7^iii	1.276 (12)
Tb1—O6	2.514 (10)	C9—O8^iv	1.276 (12)
Tb1—O1	2.555 (8)	C10—H10	0.9300
Tb1—Tb1^i	3.9071 (9)	C11—O5	1.244 (18)
C1—C2	1.55 (2)	C11—N1	1.35 (2)
C1—H1A	0.9600	C11—C12	1.52 (2)
C1—H1B	0.9600	C12—H12A	0.9600
C1—H1C	0.9600	C12—H12B	0.9600
C2—O2	1.221 (15)	C12—H12C	0.9600
C2—O1	1.252 (14)	C13—N1	1.66 (3)
C3—O4	1.263 (14)	C13—H13A	0.9600
C3—O3	1.305 (14)	C13—H13B	0.9600
C3—C4	1.467 (15)	C13—H13C	0.9600
C4—C5	1.396 (15)	C14—N1	1.51 (3)
C4—C10	1.384 (15)	C14—H14A	0.9600
C5—C6	1.362 (15)	C14—H14B	0.9600
C5—H5	0.9300	C14—H14C	0.9600
O5—Tb1—O1^i	80.4 (3)	O3—C3—C4	118.5 (10)
O5—Tb1—O7	85.5 (4)	C5—C4—C10	118.2 (9)
O1^i—Tb1—O7	75.0 (3)	C5—C4—C3	123.5 (10)
O5—Tb1—O8	120.3 (3)	C10—C4—C3	118.1 (10)
O1^i—Tb1—O8	77.1 (3)	C6—C5—C4	123.4 (10)
O7—Tb1—O8	137.8 (2)	C6—C5—H5	118.3
O5—Tb1—O4	87.1 (3)	C4—C5—H5	118.3
O1^i—Tb1—O4	148.5 (3)	C5—C6—C7	116.5 (10)
O7—Tb1—O4	132.9 (2)	C5—C6—C6^ii	122.9 (12)
O8—Tb1—O4	84.6 (2)	C7—C6—C6^ii	120.7 (11)
O5—Tb1—O2	152.2 (4)	C8—C7—C6	122.7 (9)
O1^i—Tb1—O2	124.1 (3)	C8—C7—H7	118.7
O7—Tb1—O2	88.7 (3)	C6—C7—H7	118.7
O8—Tb1—O2	81.3 (3)	C7—C8—C10	118.2 (9)
O4—Tb1—O2	77.1 (3)	C7—C8—C9	121.8 (8)
O5—Tb1—O3	76.6 (3)	C10—C8—C9	120.0 (9)
O1^i—Tb1—O3	146.8 (3)	O7^iii—C9—O8^iv	125.0 (10)
O7—Tb1—O3	79.5 (3)	O7^iii—C9—C8	116.9 (8)
O8—Tb1—O3	135.5 (3)	O8^iv—C9—C8	117.6 (9)
O4—Tb1—O3	53.6 (2)	C4—C10—C8	121.1 (10)
O2—Tb1—O3	75.6 (3)	C4—C10—H10	119.5
O5—Tb1—O6	56.9 (4)	C8—C10—H10	119.5
O1^i—Tb1—O6	75.9 (4)	O5—C11—N1	113.7 (16)
O7—Tb1—O6	135.5 (4)	O5—C11—C12	132.2 (17)
O8—Tb1—O6	64.1 (3)	N1—C11—C12	113.4 (17)
O4—Tb1—O6	73.1 (3)	C11—C12—H12A	109.5
O2—Tb1—O6	135.7 (4)	C11—C12—H12B	109.5
O3—Tb1—O6	109.9 (3)	H12A—C12—H12B	109.5
O5—Tb1—O1	148.1 (3)	C11—C12—H12C	109.5
O1^i—Tb1—O1	73.7 (3)	H12A—C12—H12C	109.5
O7—Tb1—O1	70.3 (3)	H12B—C12—H12C	109.5
O8—Tb1—O1	71.8 (2)	N1—C13—H13A	109.5
O4—Tb1—O1	124.5 (3)	N1—C13—H13B	109.5
O2—Tb1—O1	50.6 (2)	H13A—C13—H13B	109.5
O3—Tb1—O1	116.9 (3)	N1—C13—H13C	109.5
O6—Tb1—O1	130.7 (3)	H13A—C13—H13C	109.5
O5—Tb1—Tb1^i	117.2 (3)	H13B—C13—H13C	109.5
O1^i—Tb1—Tb1^i	38.88 (19)	N1—C14—H14A	109.5
O7—Tb1—Tb1^i	68.02 (18)	N1—C14—H14B	109.5
O8—Tb1—Tb1^i	70.35 (16)	H14A—C14—H14B	109.5
O4—Tb1—Tb1^i	151.3 (2)	N1—C14—H14C	109.5
O2—Tb1—Tb1^i	85.32 (19)	H14A—C14—H14C	109.5
O3—Tb1—Tb1^i	142.58 (18)	H14B—C14—H14C	109.5
O6—Tb1—Tb1^i	106.3 (3)	C9^v—O8—Tb1	134.9 (7)
O1—Tb1—Tb1^i	34.82 (16)	C11—N1—C14	138.6 (19)
C2—C1—H1A	109.5	C11—N1—C13	114.3 (17)
C2—C1—H1B	109.5	C14—N1—C13	106.9 (15)
H1A—C1—H1B	109.5	C2—O1—Tb1^i	160.8 (8)
C2—C1—H1C	109.5	C2—O1—Tb1	91.8 (7)
H1A—C1—H1C	109.5	Tb1^i—O1—Tb1	106.3 (3)
H1B—C1—H1C	109.5	C2—O2—Tb1	97.7 (8)
O2—C2—O1	119.9 (12)	C3—O3—Tb1	91.1 (6)
O2—C2—C1	120.3 (12)	C3—O4—Tb1	95.8 (6)
O1—C2—C1	119.6 (12)	C11—O5—Tb1	146.9 (11)
O4—C3—O3	119.5 (10)	C9^vi—O7—Tb1	140.2 (7)
O4—C3—C4	122.0 (10)

Symmetry codes: (i) −x+1, −y, −z; (ii) −x+1, −y+1, −z; (iii) x+1/2, −y+1/2, z+1/2; (iv) −x+3/2, y+1/2, −z+1/2; (v) −x+3/2, y−1/2, −z+1/2; (vi) x−1/2, −y+1/2, z−1/2.

Poly[[tetraaquatetra-µ₂-acetato-bis(µ₅-biphenyl-3,3',5,5'-tetracarboxylato)tetrakis(dimethylacetamide)tetraeuropium(III)] tetraahydrate] (140903a)

Crystal data

[Eu4(C16H6O8)2(C2H3O2)4(C4H9NO)4(H2O)4]·4H2O	F(000) = 932
Mr = 1908.92	Dx = 1.678 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.4453 (5) Å	Cell parameters from 2715 reflections
b = 17.7439 (14) Å	θ = 2.5–24.7°
c = 11.3019 (8) Å	µ = 3.36 mm^−1
β = 94.278 (1)°	T = 298 K
V = 1888.9 (2) Å^3	Bloc, colorless
Z = 1	0.16 × 0.14 × 0.13 mm

Data collection

Bruker APEXII CCD diffractometer	2250 reflections with I > 2σ(I)
φ and ω scans	Rint = 0.101
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θmax = 25.0°, θmin = 2.5°
Tmin = 0.562, Tmax = 0.610	h = −10→11
8950 measured reflections	k = −12→21
3206 independent reflections	l = −13→13

Refinement

Refinement on F^2	479 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.072	H-atom parameters constrained
wR(F^2) = 0.196	w = 1/[σ^2(Fo^2) + (0.130P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.96	(Δ/σ)max = 0.009
3206 reflections	Δρmax = 1.42 e Å^−3
208 parameters	Δρmin = −2.35 e Å^−3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Eu1	0.51698 (6)	0.89862 (3)	0.92988 (5)	0.0376 (3)
N1	0.9264 (13)	0.8207 (8)	0.8248 (12)	0.100 (3)
O1	0.4120 (10)	0.7872 (5)	0.8308 (8)	0.0592 (16)
O2	0.5616 (10)	0.7626 (5)	0.9825 (8)	0.0625 (16)
O3	0.7192 (13)	0.8708 (7)	0.8418 (11)	0.085 (2)
O4	0.6641 (11)	0.9131 (5)	1.1088 (9)	0.0650 (19)
O5	0.3915 (10)	0.9787 (5)	1.0828 (8)	0.0582 (18)
O6	0.3212 (11)	0.8642 (5)	1.0502 (9)	0.0670 (18)
O7	0.3275 (10)	0.9667 (4)	0.8285 (8)	0.0635 (19)
C1	0.4730 (16)	0.7393 (7)	0.8984 (12)	0.0600 (18)
C2	0.4446 (9)	0.6571 (2)	0.8898 (7)	0.0526 (18)
C3	0.5031 (9)	0.6042 (3)	0.9700 (6)	0.0540 (19)
H3	0.566175	0.619495	1.032562	0.065*
C4	0.4674 (9)	0.5286 (3)	0.9567 (6)	0.052 (2)
C5	0.3731 (8)	0.5058 (2)	0.8632 (6)	0.052 (2)
H5	0.349238	0.455135	0.854296	0.062*
C6	0.3146 (9)	0.5586 (3)	0.7830 (6)	0.0520 (19)
C13	0.3504 (9)	0.6343 (3)	0.7964 (6)	0.0521 (18)
H13	0.311202	0.669704	0.742719	0.063*
C7	0.2154 (14)	0.5359 (6)	0.6759 (11)	0.054 (2)
C8	0.3091 (17)	0.9273 (8)	1.1000 (14)	0.067 (2)
C9	0.193 (2)	0.9383 (11)	1.1838 (17)	0.091 (4)
H9A	0.220701	0.914410	1.258213	0.137*
H9B	0.106805	0.916322	1.150012	0.137*
H9C	0.179436	0.991221	1.196354	0.137*
C10	0.7862 (14)	0.8291 (10)	0.7675 (13)	0.086 (2)
C11	0.740 (2)	0.8014 (12)	0.6496 (14)	0.114 (4)
H11A	0.815069	0.772318	0.619042	0.171*
H11B	0.657576	0.770413	0.653985	0.171*
H11C	0.717887	0.843394	0.597868	0.171*
C12	1.0479 (16)	0.7814 (12)	0.7793 (16)	0.110 (4)
H12A	1.024538	0.766445	0.698554	0.164*
H12B	1.070271	0.737562	0.826829	0.164*
H12C	1.128474	0.814545	0.782715	0.164*
C14	0.9812 (18)	0.8599 (12)	0.9338 (13)	0.112 (4)
H14A	1.056226	0.893534	0.915605	0.168*
H14B	1.017085	0.823600	0.991400	0.168*
H14C	0.905964	0.888232	0.965305	0.168*
O10	0.5293 (16)	0.9187 (8)	0.7041 (12)	0.107 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Eu1	0.0459 (4)	0.0217 (4)	0.0418 (4)	0.0030 (2)	−0.0201 (2)	−0.0038 (2)
N1	0.112 (6)	0.085 (6)	0.102 (6)	0.008 (6)	−0.004 (6)	0.003 (5)
O1	0.079 (3)	0.035 (3)	0.058 (3)	0.003 (3)	−0.031 (3)	−0.003 (3)
O2	0.079 (3)	0.038 (3)	0.064 (3)	0.000 (3)	−0.034 (3)	−0.005 (3)
O3	0.099 (4)	0.067 (4)	0.089 (4)	0.004 (4)	−0.002 (4)	−0.011 (4)
O4	0.086 (4)	0.038 (3)	0.065 (4)	−0.004 (3)	−0.035 (3)	−0.011 (3)
O5	0.077 (4)	0.031 (3)	0.063 (4)	−0.002 (3)	−0.015 (3)	−0.009 (3)
O6	0.088 (4)	0.042 (3)	0.069 (3)	−0.008 (3)	−0.015 (3)	−0.006 (3)
O7	0.085 (4)	0.029 (3)	0.070 (4)	0.004 (3)	−0.038 (4)	−0.006 (3)
C1	0.078 (4)	0.039 (3)	0.059 (3)	0.000 (3)	−0.026 (3)	−0.002 (3)
C2	0.071 (4)	0.030 (3)	0.052 (3)	−0.001 (3)	−0.032 (3)	−0.001 (3)
C3	0.073 (4)	0.031 (3)	0.052 (3)	−0.002 (3)	−0.033 (3)	−0.004 (3)
C4	0.072 (4)	0.028 (4)	0.051 (4)	−0.001 (4)	−0.033 (4)	0.001 (3)
C5	0.072 (4)	0.028 (4)	0.050 (4)	−0.003 (4)	−0.037 (4)	−0.002 (3)
C6	0.070 (4)	0.030 (3)	0.051 (4)	0.000 (3)	−0.031 (3)	0.001 (3)
C13	0.070 (4)	0.031 (3)	0.049 (3)	−0.003 (3)	−0.030 (3)	−0.002 (3)
C7	0.074 (5)	0.029 (4)	0.053 (4)	−0.003 (4)	−0.034 (4)	0.001 (4)
C8	0.088 (5)	0.039 (4)	0.071 (5)	−0.005 (4)	−0.008 (4)	−0.008 (4)
C9	0.104 (9)	0.083 (8)	0.090 (9)	−0.015 (8)	0.023 (8)	−0.019 (8)
C10	0.100 (5)	0.068 (4)	0.088 (4)	0.003 (4)	−0.014 (4)	−0.007 (4)
C11	0.128 (8)	0.102 (8)	0.110 (8)	0.012 (8)	0.001 (7)	−0.011 (7)
C12	0.125 (8)	0.098 (8)	0.105 (8)	0.018 (8)	0.001 (8)	−0.004 (8)
C14	0.124 (8)	0.097 (8)	0.112 (8)	0.012 (7)	−0.010 (7)	0.000 (7)
O10	0.133 (7)	0.103 (7)	0.084 (5)	0.017 (7)	0.006 (6)	−0.006 (6)

Geometric parameters (Å, º)

Eu1—O3	2.273 (12)	C3—C4	1.3900
Eu1—O5^i	2.351 (8)	C3—H3	0.9300
Eu1—O4	2.381 (9)	C4—C5	1.3900
Eu1—O7	2.381 (8)	C4—C4^iv	1.508 (7)
Eu1—O1	2.445 (8)	C5—C6	1.3900
Eu1—O6	2.453 (11)	C5—H5	0.9300
Eu1—O2	2.514 (9)	C6—C13	1.3900
Eu1—O10	2.587 (14)	C6—C7	1.529 (12)
Eu1—O5	2.592 (9)	C13—H13	0.9300
Eu1—Eu1^i	3.9540 (10)	C8—C9	1.51 (2)
N1—C10	1.437 (11)	C9—H9A	0.9600
N1—C12	1.468 (7)	C9—H9B	0.9600
N1—C14	1.475 (7)	C9—H9C	0.9600
O1—C1	1.255 (15)	C10—C11	1.456 (10)
O2—C1	1.287 (16)	C11—H11A	0.9600
O3—C10	1.316 (18)	C11—H11B	0.9600
O4—C7^ii	1.255 (14)	C11—H11C	0.9600
O5—C8	1.223 (16)	C12—H12A	0.9600
O6—C8	1.263 (18)	C12—H12B	0.9600
O7—C7^iii	1.293 (14)	C12—H12C	0.9600
C1—C2	1.484 (14)	C14—H14A	0.9600
C2—C3	1.3900	C14—H14B	0.9600
C2—C13	1.3900	C14—H14C	0.9600
O3—Eu1—O5^i	81.3 (4)	C7^iii—O7—Eu1	136.3 (7)
O3—Eu1—O4	86.5 (4)	O2—C1—O1	118.4 (11)
O5^i—Eu1—O4	76.0 (3)	O2—C1—C2	118.0 (10)
O3—Eu1—O7	121.7 (4)	O1—C1—C2	123.6 (10)
O5^i—Eu1—O7	76.6 (3)	C3—C2—C13	120.0
O4—Eu1—O7	136.4 (3)	C3—C2—C1	124.0 (6)
O3—Eu1—O1	87.1 (4)	C13—C2—C1	116.0 (6)
O5^i—Eu1—O1	149.2 (3)	C2—C3—C4	120.0
O4—Eu1—O1	131.9 (3)	C2—C3—H3	120.0
O7—Eu1—O1	85.7 (3)	C4—C3—H3	120.0
O3—Eu1—O6	151.8 (4)	C5—C4—C3	120.0
O5^i—Eu1—O6	124.1 (3)	C5—C4—C4^iv	120.3 (8)
O4—Eu1—O6	88.4 (4)	C3—C4—C4^iv	119.7 (8)
O7—Eu1—O6	79.8 (4)	C4—C5—C6	120.0
O1—Eu1—O6	75.9 (3)	C4—C5—H5	120.0
O3—Eu1—O2	76.3 (4)	C6—C5—H5	120.0
O5^i—Eu1—O2	148.0 (3)	C5—C6—C13	120.0
O4—Eu1—O2	79.9 (3)	C5—C6—C7	121.9 (6)
O7—Eu1—O2	135.0 (3)	C13—C6—C7	118.1 (6)
O1—Eu1—O2	52.2 (2)	C6—C13—C2	120.0
O6—Eu1—O2	75.5 (3)	C6—C13—H13	120.0
O3—Eu1—O10	59.8 (4)	C2—C13—H13	120.0
O5^i—Eu1—O10	76.6 (4)	O4^v—C7—O7^vi	123.8 (10)
O4—Eu1—O10	139.2 (5)	O4^v—C7—C6	118.3 (9)
O7—Eu1—O10	62.8 (4)	O7^vi—C7—C6	116.9 (9)
O1—Eu1—O10	72.9 (4)	O5—C8—O6	120.7 (14)
O6—Eu1—O10	132.2 (4)	O5—C8—C9	120.1 (14)
O2—Eu1—O10	110.3 (4)	O6—C8—C9	119.2 (14)
O3—Eu1—O5	148.5 (4)	C8—C9—H9A	109.5
O5^i—Eu1—O5	73.8 (3)	C8—C9—H9B	109.5
O4—Eu1—O5	69.0 (3)	H9A—C9—H9B	109.5
O7—Eu1—O5	71.2 (3)	C8—C9—H9C	109.5
O1—Eu1—O5	124.0 (3)	H9A—C9—H9C	109.5
O6—Eu1—O5	50.6 (3)	H9B—C9—H9C	109.5
O2—Eu1—O5	116.4 (3)	O3—C10—C11	130.5 (14)
O10—Eu1—O5	129.7 (4)	O3—C10—N1	104.0 (10)
O3—Eu1—Eu1^i	118.0 (3)	C11—C10—N1	125.4 (13)
O5^i—Eu1—Eu1^i	39.0 (2)	C10—C11—H11A	109.5
O4—Eu1—Eu1^i	67.7 (2)	C10—C11—H11B	109.5
O7—Eu1—Eu1^i	69.56 (19)	H11A—C11—H11B	109.5
O1—Eu1—Eu1^i	151.3 (2)	C10—C11—H11C	109.5
O6—Eu1—Eu1^i	85.3 (2)	H11A—C11—H11C	109.5
O2—Eu1—Eu1^i	142.7 (2)	H11B—C11—H11C	109.5
O10—Eu1—Eu1^i	106.3 (3)	N1—C12—H12A	109.5
O5—Eu1—Eu1^i	34.82 (19)	N1—C12—H12B	109.5
C10—N1—C12	127.6 (8)	H12A—C12—H12B	109.5
C10—N1—C14	125.5 (8)	N1—C12—H12C	109.5
C12—N1—C14	106.3 (8)	H12A—C12—H12C	109.5
C1—O1—Eu1	96.7 (7)	H12B—C12—H12C	109.5
C1—O2—Eu1	92.6 (7)	N1—C14—H14A	109.5
C10—O3—Eu1	149.4 (10)	N1—C14—H14B	109.5
C7^ii—O4—Eu1	139.9 (8)	H14A—C14—H14B	109.5
C8—O5—Eu1^i	160.2 (9)	N1—C14—H14C	109.5
C8—O5—Eu1	91.5 (8)	H14A—C14—H14C	109.5
Eu1^i—O5—Eu1	106.2 (3)	H14B—C14—H14C	109.5
C8—O6—Eu1	97.1 (9)

Symmetry codes: (i) −x+1, −y+2, −z+2; (ii) x+1/2, −y+3/2, z+1/2; (iii) −x+1/2, y+1/2, −z+3/2; (iv) −x+1, −y+1, −z+2; (v) x−1/2, −y+3/2, z−1/2; (vi) −x+1/2, y−1/2, −z+3/2.