Two-dimensional rare-earth-metal coordination polymers based on biphenyl-3,3′,5,5′-tetra­carb­oxy­lic acid displaying luminescence

Two coordination polymers were rationally designed and successfully con­struc­ted using the rigid multi­carb­oxy­lic acid ligand biphenyl-3,3′,5,5′-tetra­carb­oxy­lic acid (H₄BPTC) and rare earth metal ions (Eu³⁺ and Ho³⁺) under solvothermal conditions. The com­pounds are poly[[tetra-μ₂-acetato-bis(μ₆-biphenyl-3,3′,5,5′-tetra­carboxyl­ato)tetra­kis­(di­methyl­acetamide)­tetra­euro­pium(III)] di­methyl­acetamide disolvate dihydrate], {[Eu₄(C₁₆H₆O₈)₂(C₂H₃O₂)₄(C₄H₉NO)₄]·2C₄H₉NO·2H₂O}_n, and poly[[tetra-μ₂-acetato-bis­(μ₆-biphenyl-3,3′,5,5′-tetra­carboxyl­ato)tetra­kis­(di­methyl­acetamide)­tetra­holmium(III)] penta­hy­drate], {[Ho₄(C₁₆H₆O₈)₂(C₂H₃O₂)₄(C₄H₉NO)₄]·5H₂O}_n, Single-crystal X-ray diffraction analysis reveals that both polymers possess a two-dimensional structure and they also display good thermal stability up to ca 280 °C and photoluminescence with an orange–red light emission.

Computing details

For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Poly[[tetra-µ₂-acetato-bis(µ₆-biphenyl-3,3',5,5'-tetracarboxylato)tetrakis(dimethylacetamide)tetraholmium(III)] pentahydrate] (bptcho)

Crystal data

[Ho4(C16H6O8)2(C2H3O2)4(C4H9NO)4]·5H2O	F(000) = 966
Mr = 1986.88	Dx = 1.807 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.0957 (3) Å	Cell parameters from 3885 reflections
b = 17.4571 (4) Å	θ = 4.2–28.7°
c = 11.5422 (3) Å	µ = 4.37 mm^−1
β = 95.107 (3)°	T = 294 K
V = 1825.45 (9) Å^3	Plate, colourless
Z = 1	0.22 × 0.21 × 0.1 mm

Data collection

Rigaku OD SuperNova Dual source diffractometer with an EosS2 detector	3376 independent reflections
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source	2935 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.034
Detector resolution: 8.0528 pixels mm^-1	θmax = 25.5°, θmin = 3.2°
ω scans	h = −6→11
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	k = −21→20
Tmin = 0.678, Tmax = 1.000	l = −13→13
7047 measured reflections

Refinement

Refinement on F^2	492 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.032	H-atom parameters constrained
wR(F^2) = 0.082	w = 1/[σ^2(Fo^2) + (0.035P)^2 + 0.7624P] where P = (Fo^2 + 2Fc^2)/3
S = 1.05	(Δ/σ)max = 0.001
3376 reflections	Δρmax = 0.76 e Å^−3
330 parameters	Δρmin = −0.55 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)
Ho1	0.00979 (3)	0.39918 (2)	0.44251 (2)	0.02055 (11)
O1	0.1615 (5)	0.41319 (18)	0.6102 (3)	0.0338 (10)
O2	0.1653 (4)	0.53414 (17)	0.6747 (3)	0.0309 (9)
O3	0.4045 (4)	0.20839 (17)	0.8381 (3)	0.0313 (9)
O4	0.5575 (5)	0.23465 (19)	0.9895 (3)	0.0420 (12)
O5	0.109 (4)	0.517 (2)	0.426 (4)	0.027 (3)	0.53 (4)
O5A	0.123 (5)	0.517 (3)	0.422 (5)	0.029 (3)	0.47 (4)
O6	0.169 (2)	0.6381 (11)	0.4336 (17)	0.036 (3)	0.53 (4)
O6A	0.207 (2)	0.6303 (12)	0.4500 (19)	0.036 (3)	0.47 (4)
O7	0.200 (2)	0.3703 (10)	0.3431 (15)	0.052 (3)	0.63 (3)
O7A	0.190 (4)	0.3792 (16)	0.323 (3)	0.049 (3)	0.37 (3)
N1	0.3978 (19)	0.3128 (9)	0.3293 (15)	0.068 (2)	0.63 (3)
N1A	0.421 (3)	0.3118 (12)	0.334 (2)	0.068 (3)	0.37 (3)
C1	0.2035 (6)	0.4651 (3)	0.6806 (4)	0.0241 (12)
C2	0.3086 (6)	0.4410 (2)	0.7826 (4)	0.0204 (11)
C3	0.3409 (6)	0.3637 (3)	0.7961 (4)	0.0215 (11)
H3	0.299386	0.328123	0.742864	0.026*
C4	0.4362 (6)	0.3402 (2)	0.8900 (4)	0.0224 (12)
C5	0.4996 (7)	0.3933 (3)	0.9691 (5)	0.0306 (14)
H5	0.564571	0.376602	1.030691	0.037*
C6	0.4672 (6)	0.4713 (3)	0.9576 (4)	0.0234 (12)
C7	0.3692 (6)	0.4932 (2)	0.8628 (4)	0.0234 (12)
H7	0.344366	0.544704	0.853616	0.028*
C8	0.4689 (7)	0.2563 (3)	0.9077 (5)	0.0303 (14)
C9	0.283 (2)	0.3295 (9)	0.2811 (14)	0.057 (2)	0.63 (3)
C9A	0.268 (3)	0.3303 (12)	0.2899 (19)	0.058 (3)	0.37 (3)
C10	0.233 (2)	0.3072 (12)	0.1587 (14)	0.064 (4)	0.63 (3)
H10A	0.127964	0.298355	0.153873	0.096*	0.63 (3)
H10B	0.281984	0.260895	0.139593	0.096*	0.63 (3)
H10C	0.253704	0.346815	0.105003	0.096*	0.63 (3)
C10A	0.221 (3)	0.2777 (18)	0.193 (3)	0.066 (5)	0.37 (3)
H10D	0.212804	0.227375	0.225689	0.100*	0.37 (3)
H10E	0.293694	0.277065	0.137749	0.100*	0.37 (3)
H10F	0.127514	0.292925	0.155459	0.100*	0.37 (3)
C11	0.528 (2)	0.2700 (13)	0.285 (2)	0.093 (5)	0.63 (3)
H11A	0.520171	0.216879	0.305191	0.139*	0.63 (3)
H11B	0.619971	0.289959	0.320801	0.139*	0.63 (3)
H11C	0.525661	0.275259	0.202501	0.139*	0.63 (3)
C11A	0.487 (4)	0.2471 (16)	0.273 (3)	0.078 (6)	0.37 (3)
H11D	0.411980	0.209242	0.255526	0.117*	0.37 (3)
H11E	0.566221	0.225002	0.323136	0.117*	0.37 (3)
H11F	0.524411	0.264442	0.202676	0.117*	0.37 (3)
C12	0.450 (2)	0.3341 (14)	0.4512 (16)	0.085 (4)	0.63 (3)
H12A	0.403736	0.381268	0.470887	0.127*	0.63 (3)
H12B	0.554966	0.340528	0.457907	0.127*	0.63 (3)
H12C	0.423716	0.294458	0.503287	0.127*	0.63 (3)
C12A	0.468 (4)	0.3647 (19)	0.431 (3)	0.079 (6)	0.37 (3)
H12D	0.501576	0.411414	0.398031	0.118*	0.37 (3)
H12E	0.547966	0.342204	0.479841	0.118*	0.37 (3)
H12F	0.387716	0.375654	0.476841	0.118*	0.37 (3)
C13	0.207 (3)	0.5696 (16)	0.401 (3)	0.034 (2)	0.53 (4)
C13A	0.184 (3)	0.5734 (18)	0.392 (3)	0.034 (3)	0.47 (4)
C14	0.334 (3)	0.5512 (11)	0.329 (2)	0.056 (4)	0.53 (4)
H14A	0.373125	0.598211	0.301743	0.084*	0.53 (4)
H14B	0.298275	0.520301	0.263193	0.084*	0.53 (4)
H14C	0.409355	0.523881	0.375013	0.084*	0.53 (4)
C14A	0.278 (3)	0.5661 (13)	0.290 (2)	0.052 (4)	0.47 (4)
H14D	0.339227	0.610641	0.285643	0.078*	0.47 (4)
H14E	0.215237	0.561171	0.218793	0.078*	0.47 (4)
H14F	0.339237	0.521381	0.300683	0.078*	0.47 (4)
O8	0.8199 (9)	0.3103 (5)	1.0933 (6)	0.080 (2)	0.75
H8A	0.818189	0.314756	1.166430	0.120*	0.75
H8B	0.738218	0.288986	1.070823	0.120*	0.75
O9	0.024 (3)	0.487 (2)	0.044 (2)	0.114 (11)	0.25
H9A	−0.031387	0.474081	−0.016345	0.172*	0.25
H9B	0.079053	0.448131	0.058545	0.172*	0.25
O10	0.068 (4)	0.568 (2)	0.052 (3)	0.137 (11)	0.25
H10G	0.053176	0.590907	−0.012776	0.206*	0.25
H10H	0.002226	0.533427	0.050044	0.206*	0.25

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ho1	0.02803 (17)	0.00927 (14)	0.02170 (16)	0.00210 (9)	−0.01252 (11)	−0.00276 (9)
O1	0.049 (3)	0.0153 (17)	0.031 (2)	0.0063 (17)	−0.0292 (19)	−0.0077 (16)
O2	0.048 (3)	0.0094 (16)	0.031 (2)	0.0068 (16)	−0.0251 (18)	−0.0021 (15)
O3	0.051 (3)	0.0108 (16)	0.027 (2)	0.0003 (16)	−0.0266 (18)	−0.0003 (15)
O4	0.062 (3)	0.0119 (18)	0.045 (2)	0.0007 (18)	−0.039 (2)	0.0010 (17)
O5	0.032 (6)	0.020 (3)	0.029 (4)	−0.004 (4)	0.005 (4)	0.001 (3)
O5A	0.033 (6)	0.023 (4)	0.031 (5)	−0.003 (4)	0.002 (5)	−0.001 (4)
O6	0.038 (6)	0.025 (4)	0.044 (5)	−0.011 (4)	−0.001 (4)	0.002 (4)
O6A	0.037 (6)	0.027 (4)	0.042 (5)	−0.006 (5)	−0.001 (5)	−0.001 (4)
O7	0.051 (4)	0.046 (4)	0.060 (5)	0.014 (4)	0.018 (4)	−0.013 (4)
O7A	0.048 (5)	0.048 (5)	0.052 (6)	0.010 (4)	0.010 (5)	−0.008 (5)
N1	0.052 (4)	0.076 (4)	0.076 (4)	0.014 (4)	−0.002 (4)	−0.008 (4)
N1A	0.054 (5)	0.074 (5)	0.074 (5)	0.013 (4)	0.002 (4)	−0.009 (4)
C1	0.029 (3)	0.019 (3)	0.022 (3)	0.001 (2)	−0.013 (2)	−0.001 (2)
C2	0.027 (3)	0.011 (2)	0.021 (3)	−0.001 (2)	−0.011 (2)	0.004 (2)
C3	0.030 (3)	0.013 (2)	0.019 (3)	−0.001 (2)	−0.010 (2)	−0.004 (2)
C4	0.038 (3)	0.008 (2)	0.019 (3)	0.001 (2)	−0.016 (2)	−0.001 (2)
C5	0.043 (4)	0.016 (3)	0.029 (3)	0.007 (2)	−0.021 (3)	0.003 (2)
C6	0.036 (3)	0.011 (2)	0.020 (3)	−0.006 (2)	−0.014 (2)	0.002 (2)
C7	0.031 (3)	0.006 (2)	0.030 (3)	0.001 (2)	−0.016 (2)	−0.001 (2)
C8	0.046 (4)	0.010 (2)	0.031 (3)	0.000 (2)	−0.019 (3)	0.002 (2)
C9	0.050 (4)	0.056 (4)	0.065 (4)	0.006 (4)	0.009 (3)	−0.010 (3)
C9A	0.052 (4)	0.058 (4)	0.065 (4)	0.007 (4)	0.008 (4)	−0.010 (4)
C10	0.077 (7)	0.057 (8)	0.057 (7)	0.011 (7)	0.002 (6)	−0.012 (6)
C10A	0.074 (9)	0.061 (10)	0.066 (10)	0.000 (9)	0.016 (8)	−0.021 (8)
C11	0.065 (9)	0.103 (9)	0.110 (8)	0.031 (7)	0.007 (7)	−0.031 (8)
C11A	0.051 (10)	0.079 (10)	0.103 (10)	0.023 (8)	0.002 (9)	−0.021 (9)
C12	0.076 (8)	0.091 (9)	0.085 (8)	0.008 (8)	−0.005 (7)	−0.003 (7)
C12A	0.068 (9)	0.086 (10)	0.080 (10)	0.006 (10)	−0.008 (8)	0.001 (9)
C13	0.036 (5)	0.030 (4)	0.035 (4)	−0.005 (4)	0.006 (4)	−0.001 (3)
C13A	0.036 (5)	0.031 (4)	0.035 (4)	−0.004 (4)	0.003 (4)	0.000 (4)
C14	0.055 (9)	0.057 (7)	0.059 (9)	−0.007 (7)	0.021 (7)	0.005 (7)
C14A	0.053 (9)	0.052 (8)	0.051 (8)	−0.013 (7)	0.006 (7)	−0.010 (7)
O8	0.086 (6)	0.087 (5)	0.060 (5)	−0.031 (4)	−0.037 (4)	0.019 (4)
O9	0.08 (2)	0.18 (4)	0.08 (2)	0.04 (2)	0.033 (18)	0.03 (2)
O10	0.14 (2)	0.182 (19)	0.090 (17)	0.019 (17)	0.023 (15)	0.016 (16)

Geometric parameters (Å, º)

Ho1—O1	2.288 (3)	C6—C7	1.402 (6)
Ho1—O2^i	2.311 (3)	C7—H7	0.9300
Ho1—O3^ii	2.385 (3)	C9—C10	1.498 (18)
Ho1—O4^ii	2.429 (3)	C9A—C10A	1.478 (10)
Ho1—O5^i	2.43 (5)	C10—H10A	0.9600
Ho1—O5	2.26 (3)	C10—H10B	0.9601
Ho1—O5A^i	2.53 (6)	C10—H10C	0.9597
Ho1—O5A	2.32 (3)	C10A—H10D	0.9597
Ho1—O6^i	2.352 (19)	C10A—H10E	0.9600
Ho1—O6A^i	2.47 (2)	C10A—H10F	0.9600
Ho1—O7	2.221 (15)	C11—H11A	0.9590
Ho1—O7A	2.26 (3)	C11—H11B	0.9599
O1—C1	1.254 (6)	C11—H11C	0.9601
O2—C1	1.254 (5)	C11A—H11D	0.9601
O3—C8	1.266 (6)	C11A—H11E	0.9603
O4—C8	1.245 (6)	C11A—H11F	0.9598
O5—C13	1.33 (2)	C12—H12A	0.9602
O5A—C13A	1.200 (10)	C12—H12B	0.9599
O6—C13	1.31 (4)	C12—H12C	0.9599
O6A—C13A	1.21 (5)	C12A—H12D	0.9600
O7—C9	1.298 (15)	C12A—H12E	0.9601
O7A—C9A	1.196 (10)	C12A—H12F	0.9600
N1—C9	1.17 (2)	C13—C14	1.51 (3)
N1—C11	1.528 (18)	C13A—C14A	1.52 (4)
N1—C12	1.490 (17)	C14—H14A	0.9597
N1A—C9A	1.474 (10)	C14—H14B	0.9604
N1A—C11A	1.485 (10)	C14—H14C	0.9601
N1A—C12A	1.485 (10)	C14A—H14D	0.9601
C1—C2	1.509 (6)	C14A—H14E	0.9601
C2—C3	1.386 (7)	C14A—H14F	0.9600
C2—C7	1.379 (6)	O8—H8A	0.8497
C3—H3	0.9300	O8—H8B	0.8500
C3—C4	1.388 (6)	O9—O9^iv	1.16 (5)
C4—C5	1.389 (7)	O9—H9A^iv	0.76 (7)
C4—C8	1.505 (6)	O9—H9A	0.8502
C5—H5	0.9300	O9—H9B	0.8496
C5—C6	1.397 (6)	O10—H10G	0.8504
C6—C6^iii	1.488 (9)	O10—H10H	0.8499
O1—Ho1—O2^i	140.70 (11)	C7—C6—C6^iii	121.3 (5)
O1—Ho1—O3^ii	134.13 (11)	C2—C7—C6	122.1 (4)
O1—Ho1—O4^ii	80.30 (12)	C2—C7—H7	118.9
O1—Ho1—O5^i	71.0 (12)	C6—C7—H7	118.9
O1—Ho1—O5A	75.8 (15)	O3—C8—Ho1^v	59.5 (2)
O1—Ho1—O5A^i	72.4 (13)	O3—C8—C4	118.8 (4)
O1—Ho1—O6^i	85.0 (5)	O4—C8—Ho1^v	61.4 (2)
O1—Ho1—O6A^i	92.6 (5)	O4—C8—O3	120.8 (4)
O2^i—Ho1—O3^ii	82.88 (11)	O4—C8—C4	120.3 (4)
O2^i—Ho1—O4^ii	135.69 (12)	C4—C8—Ho1^v	176.3 (4)
O2^i—Ho1—O5^i	75.0 (12)	O7—C9—C10	121.1 (17)
O2^i—Ho1—O5A	77.4 (14)	N1—C9—O7	114.1 (19)
O2^i—Ho1—O5A^i	74.3 (13)	N1—C9—C10	124.7 (18)
O2^i—Ho1—O6^i	91.0 (5)	O7A—C9A—N1A	128 (3)
O2^i—Ho1—O6A^i	82.0 (5)	O7A—C9A—C10A	123 (3)
O3^ii—Ho1—O4^ii	53.94 (11)	N1A—C9A—C10A	109 (2)
O3^ii—Ho1—O5^i	127.5 (8)	C9—C10—H10A	108.5
O3^ii—Ho1—O5A^i	125.3 (9)	C9—C10—H10B	108.9
O3^ii—Ho1—O6A^i	77.7 (5)	C9—C10—H10C	111.0
O4^ii—Ho1—O5^i	121.3 (9)	H10A—C10—H10B	109.5
O4^ii—Ho1—O5A^i	120.3 (10)	H10A—C10—H10C	109.5
O4^ii—Ho1—O6A^i	79.7 (5)	H10B—C10—H10C	109.5
O5—Ho1—O1	76.1 (13)	C9A—C10A—H10D	107.6
O5—Ho1—O2^i	75.6 (13)	C9A—C10A—H10E	109.9
O5—Ho1—O3^ii	144.9 (13)	C9A—C10A—H10F	110.9
O5—Ho1—O4^ii	146.1 (12)	H10D—C10A—H10E	109.5
O5—Ho1—O5^i	73.1 (14)	H10D—C10A—H10F	109.5
O5^i—Ho1—O5A^i	2.2 (16)	H10E—C10A—H10F	109.5
O5—Ho1—O5A^i	75.0 (14)	N1—C11—H11A	108.4
O5—Ho1—O6^i	127.3 (12)	N1—C11—H11B	110.6
O5^i—Ho1—O6A^i	52.7 (8)	N1—C11—H11C	109.4
O5—Ho1—O6A^i	125.0 (13)	H11A—C11—H11B	109.5
O6^i—Ho1—O3^ii	79.7 (5)	H11A—C11—H11C	109.5
O6^i—Ho1—O4^ii	73.6 (5)	H11B—C11—H11C	109.5
O6^i—Ho1—O5^i	54.2 (8)	N1A—C11A—H11D	108.3
O6^i—Ho1—O5A^i	52.4 (8)	N1A—C11A—H11E	109.6
O6^i—Ho1—O6A^i	9.0 (7)	N1A—C11A—H11F	110.5
O7—Ho1—O1	91.2 (6)	H11D—C11A—H11E	109.5
O7—Ho1—O2^i	110.0 (5)	H11D—C11A—H11F	109.5
O7—Ho1—O3^ii	81.8 (6)	H11E—C11A—H11F	109.5
O7—Ho1—O4^ii	76.4 (5)	N1—C12—H12A	109.2
O7—Ho1—O5^i	150.5 (9)	N1—C12—H12B	109.6
O7—Ho1—O5	80.1 (13)	N1—C12—H12C	109.7
O7—Ho1—O5A^i	152.7 (9)	H12A—C12—H12B	109.4
O7—Ho1—O6^i	150.0 (7)	H12A—C12—H12C	109.4
O7—Ho1—O6A^i	154.8 (7)	H12B—C12—H12C	109.5
O7A—Ho1—O1	96.6 (9)	N1A—C12A—H12D	108.0
O7A—Ho1—O5A	73.8 (16)	N1A—C12A—H12E	109.8
C1—O1—Ho1	138.7 (3)	N1A—C12A—H12F	110.6
C1—O2—Ho1^i	133.6 (3)	H12D—C12A—H12E	109.5
C8—O3—Ho1^v	93.3 (3)	H12D—C12A—H12F	109.5
C8—O4—Ho1^v	91.8 (3)	H12E—C12A—H12F	109.5
Ho1—O5—Ho1^i	106.9 (13)	O5—C13—Ho1^i	58 (3)
C13—O5—Ho1	158 (4)	O5—C13—C14	122 (3)
C13—O5—Ho1^i	94 (3)	O6—C13—Ho1^i	54.9 (15)
Ho1—O5A—Ho1^i	102.1 (15)	O6—C13—O5	111 (4)
C13A—O5A—Ho1	169 (5)	O6—C13—C14	126 (2)
C13—O6—Ho1^i	98.0 (17)	C14—C13—Ho1^i	174.1 (17)
C9—O7—Ho1	158.2 (15)	O5A—C13A—O6A	125 (5)
C9A—O7A—Ho1	142.2 (16)	O5A—C13A—C14A	117 (4)
C9—N1—C11	130.4 (17)	O6A—C13A—C14A	115 (3)
C9—N1—C12	125.4 (18)	C13—C14—H14A	108.8
C12—N1—C11	104.1 (18)	C13—C14—H14B	109.7
C9A—N1A—C11A	114 (2)	C13—C14—H14C	110.0
C9A—N1A—C12A	109 (2)	H14A—C14—H14B	109.5
C11A—N1A—C12A	137 (3)	H14A—C14—H14C	109.5
O1—C1—O2	126.3 (5)	H14B—C14—H14C	109.5
O1—C1—C2	116.1 (4)	C13A—C14A—H14D	109.8
O2—C1—C2	117.6 (4)	C13A—C14A—H14E	109.5
C3—C2—C1	118.2 (4)	C13A—C14A—H14F	109.1
C7—C2—C1	121.8 (4)	H14D—C14A—H14E	109.5
C7—C2—C3	120.0 (4)	H14D—C14A—H14F	109.5
C2—C3—H3	120.4	H14E—C14A—H14F	109.5
C2—C3—C4	119.1 (4)	H8A—O8—H8B	104.5
C4—C3—H3	120.4	O9^iv—O9—H9A	40.7
C3—C4—C5	120.7 (4)	O9^iv—O9—H9A^iv	47 (3)
C3—C4—C8	119.7 (4)	O9^iv—O9—H9B	131.4
C5—C4—C8	119.6 (4)	H9A—O9—H9A^iv	88.0
C4—C5—H5	119.5	H9A—O9—H9B	104.5
C4—C5—C6	121.0 (5)	H9B—O9—H9A^iv	136.9
C6—C5—H5	119.5	H10G—O10—H9A^iv	87.1
C5—C6—C6^iii	121.7 (6)	H10G—O10—H10H	104.5
C5—C6—C7	117.0 (4)	H10H—O10—H9A^iv	33.6

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O8	0.93	2.64	3.449 (10)	146
C10—H10B···O6^vi	0.96	2.36	3.29 (2)	162
C11—H11B···O3^vii	0.96	2.58	3.44 (2)	150
C11A—H11F···O4^viii	0.96	2.56	3.40 (3)	147
C12—H12C···O8^ii	0.96	2.34	3.28 (3)	166
C12A—H12E···O6A^ix	0.96	2.35	3.15 (4)	139
C14A—H14F···O7A	0.96	2.85	3.39 (4)	116
O8—H8A···O3^v	0.85	2.10	2.881 (7)	152
O8—H8B···O4	0.85	2.05	2.892 (8)	170
O10—H10G···O8^ix	0.85	2.32	2.95 (4)	131
O10—H10H···O10^iv	0.85	2.20	2.90 (8)	140

Symmetry codes: (ii) x−1/2, −y+1/2, z−1/2; (iv) −x, −y+1, −z; (v) x+1/2, −y+1/2, z+1/2; (vi) −x+1/2, y−1/2, −z+1/2; (vii) x+1/2, −y+1/2, z−1/2; (viii) x, y, z−1; (ix) −x+1, −y+1, −z+1.

Poly[[tetra-µ₂-acetato-bis(µ₆-biphenyl-3,3',5,5'-tetracarboxylato)tetrakis(dimethylacetamide)tetraeuropium(III)] dimethylacetamide disolvate dihydrate] (bptceu)

Crystal data

[Eu4(C16H6O8)2(C2H3O2)4(C4H9NO)4]·2C4H9NO·2H2O	F(000) = 1016
Mr = 2055.20	Dx = 1.848 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 9.3197 (4) Å	Cell parameters from 2968 reflections
b = 17.6285 (6) Å	θ = 3.2–28.2°
c = 11.2707 (4) Å	µ = 3.44 mm^−1
β = 94.131 (4)°	T = 293 K
V = 1846.88 (12) Å^3	Prism, colourless
Z = 1	0.25 × 0.14 × 0.14 mm

Data collection

Rigaku R-AXIS SPIDER IP diffractometer	3254 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.034
phi and ω scans	θmax = 29.0°, θmin = 3.6°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −11→12
Tmin = 0.426, Tmax = 0.854	k = −18→23
9134 measured reflections	l = −7→15
4272 independent reflections

Refinement

Refinement on F^2	625 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.105	w = 1/[σ^2(Fo^2) + (0.0314P)^2 + 6.1561P] where P = (Fo^2 + 2Fc^2)/3
S = 1.10	(Δ/σ)max < 0.001
4272 reflections	Δρmax = 0.90 e Å^−3
363 parameters	Δρmin = −0.87 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)
Eu1	0.48218 (3)	0.10133 (2)	0.06942 (3)	0.03170 (12)
O1	0.4383 (6)	0.2377 (2)	0.0153 (4)	0.0534 (15)
O2	0.5840 (5)	0.2127 (2)	0.1712 (4)	0.0435 (12)
O3	0.8278 (6)	0.5341 (2)	0.3253 (4)	0.0534 (15)
O4	0.8362 (5)	0.4138 (2)	0.3911 (4)	0.0485 (13)
O5	0.6724 (12)	0.1379 (7)	−0.0610 (11)	0.056 (3)	0.65 (2)
O6	0.615 (2)	0.0197 (8)	−0.078 (2)	0.041 (2)	0.65 (2)
O7	0.2881 (11)	0.1249 (6)	0.1708 (10)	0.089 (3)	0.704 (10)
O8	0.4570 (15)	0.0816 (7)	0.2892 (10)	0.089 (4)	0.5
N1	0.0736 (10)	0.1864 (5)	0.1806 (10)	0.095 (3)	0.704 (10)
C1	0.5248 (8)	0.2588 (3)	0.0994 (6)	0.0386 (16)
C2	0.5584 (7)	0.3414 (3)	0.1137 (5)	0.0322 (14)
C3	0.4983 (7)	0.3951 (3)	0.0337 (5)	0.0369 (15)
H3	0.433845	0.379160	−0.028145	0.044*
C4	0.5321 (7)	0.4717 (3)	0.0440 (5)	0.0330 (14)
C5	0.6294 (7)	0.4934 (3)	0.1372 (5)	0.0381 (16)
H5	0.655733	0.544127	0.145124	0.046*
C6	0.6881 (7)	0.4409 (3)	0.2183 (5)	0.0325 (14)
C7	0.6521 (7)	0.3654 (3)	0.2071 (5)	0.0311 (14)
H7	0.690677	0.330470	0.262381	0.037*
C8	0.7926 (7)	0.4650 (3)	0.3203 (5)	0.0397 (17)
C9	0.6989 (14)	0.0719 (8)	−0.0964 (10)	0.053 (2)	0.65 (2)
C10	0.834 (2)	0.0526 (11)	−0.1631 (18)	0.080 (4)	0.65 (2)
H10A	0.887022	0.098204	−0.176179	0.121*	0.65 (2)
H10B	0.805292	0.029564	−0.238279	0.121*	0.65 (2)
H10C	0.893532	0.018024	−0.115869	0.121*	0.65 (2)
C11	0.2174 (12)	0.1659 (5)	0.2292 (10)	0.098 (3)	0.704 (10)
C12	0.2595 (16)	0.1991 (9)	0.3474 (12)	0.120 (5)	0.704 (10)
H12A	0.237935	0.163860	0.408609	0.179*	0.704 (10)
H12B	0.207055	0.245280	0.356949	0.179*	0.704 (10)
H12C	0.360795	0.209680	0.353139	0.179*	0.704 (10)
C13	−0.0330 (17)	0.2344 (8)	0.2316 (16)	0.113 (5)	0.704 (10)
H13A	−0.102866	0.203268	0.266974	0.170*	0.704 (10)
H13B	−0.080106	0.265028	0.170024	0.170*	0.704 (10)
H13C	0.013574	0.266638	0.291244	0.170*	0.704 (10)
C14	0.048 (2)	0.1490 (9)	0.0631 (12)	0.129 (5)	0.704 (10)
H14A	0.135538	0.148955	0.022809	0.194*	0.704 (10)
H14B	−0.025092	0.176015	0.016269	0.194*	0.704 (10)
H14C	0.017518	0.097635	0.074359	0.194*	0.704 (10)
C15	0.563 (3)	0.1540 (10)	0.446 (2)	0.153 (9)	0.5
H15A	0.572169	0.191818	0.385707	0.230*	0.5
H15B	0.655189	0.145208	0.487287	0.230*	0.5
H15C	0.496549	0.171368	0.501347	0.230*	0.5
O5A	0.7020 (19)	0.1326 (15)	−0.0344 (19)	0.053 (3)	0.35 (2)
O6A	0.606 (5)	0.0237 (18)	−0.084 (4)	0.046 (3)	0.35 (2)
C9A	0.678 (3)	0.0796 (18)	−0.105 (2)	0.054 (3)	0.35 (2)
C10A	0.771 (4)	0.0784 (17)	−0.218 (3)	0.065 (5)	0.35 (2)
H10D	0.722528	0.105498	−0.282689	0.097*	0.35 (2)
H10E	0.785968	0.026818	−0.240649	0.097*	0.35 (2)
H10F	0.861918	0.102028	−0.196279	0.097*	0.35 (2)
O7A	0.243 (2)	0.1370 (14)	0.111 (2)	0.090 (4)	0.296 (10)
N1A	0.003 (2)	0.1584 (13)	0.125 (2)	0.114 (4)	0.296 (10)
C11A	0.157 (2)	0.1734 (10)	0.1632 (17)	0.100 (3)	0.296 (10)
C12A	0.177 (3)	0.2313 (16)	0.260 (3)	0.110 (5)	0.296 (10)
H12D	0.151006	0.209772	0.333374	0.164*	0.296 (10)
H12E	0.116756	0.274352	0.239964	0.164*	0.296 (10)
H12F	0.275736	0.247012	0.267524	0.164*	0.296 (10)
C13A	−0.100 (3)	0.2039 (19)	0.190 (3)	0.109 (6)	0.296 (10)
H13D	−0.070390	0.204065	0.273372	0.163*	0.296 (10)
H13E	−0.194150	0.182205	0.177902	0.163*	0.296 (10)
H13F	−0.101330	0.254975	0.160362	0.163*	0.296 (10)
C14A	−0.019 (3)	0.1012 (19)	0.030 (3)	0.137 (8)	0.296 (10)
H14D	0.025800	0.118450	−0.039916	0.206*	0.296 (10)
H14E	−0.119630	0.093880	0.010484	0.206*	0.296 (10)
H14F	0.024390	0.054060	0.055944	0.206*	0.296 (10)
C18	0.471 (3)	−0.0572 (10)	0.410 (2)	0.165 (9)	0.5
H18A	0.367760	−0.055730	0.395540	0.248*	0.5
H18B	0.496730	−0.097110	0.465240	0.248*	0.5
H18C	0.513650	−0.066370	0.336470	0.248*	0.5
C16	0.5093 (13)	0.0832 (9)	0.3898 (12)	0.134 (6)	0.5
N2	0.5210 (16)	0.0147 (9)	0.4593 (13)	0.144 (6)	0.5
C17	0.584 (2)	0.0167 (15)	0.5808 (15)	0.158 (9)	0.5
H17A	0.511585	0.006131	0.634684	0.237*	0.5
H17B	0.624285	0.066051	0.597535	0.237*	0.5
H17C	0.658885	−0.020779	0.590415	0.237*	0.5
O9	0.6694 (16)	0.1951 (9)	0.4266 (12)	0.106 (5)	0.5
H9A	0.604109	0.222894	0.392659	0.159*	0.5
H9B	0.704209	0.171004	0.370009	0.159*	0.5

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Eu1	0.0399 (2)	0.01449 (16)	0.03764 (18)	0.00265 (14)	−0.01825 (13)	−0.00357 (13)
O1	0.082 (4)	0.016 (2)	0.055 (3)	−0.003 (2)	−0.046 (3)	−0.002 (2)
O2	0.069 (3)	0.016 (2)	0.040 (2)	0.003 (2)	−0.030 (2)	−0.0021 (18)
O3	0.078 (4)	0.020 (2)	0.054 (3)	−0.006 (2)	−0.050 (3)	0.001 (2)
O4	0.068 (3)	0.026 (2)	0.045 (3)	−0.006 (2)	−0.040 (2)	0.007 (2)
O5	0.073 (4)	0.035 (4)	0.061 (5)	−0.016 (4)	0.007 (4)	−0.005 (4)
O6	0.050 (4)	0.026 (3)	0.046 (4)	−0.010 (3)	0.004 (4)	−0.002 (3)
O7	0.089 (5)	0.078 (5)	0.103 (5)	0.012 (4)	0.037 (4)	−0.024 (4)
O8	0.122 (10)	0.088 (8)	0.059 (6)	0.000 (8)	0.016 (7)	0.000 (6)
N1	0.083 (5)	0.100 (5)	0.104 (5)	0.000 (4)	0.017 (4)	−0.014 (4)
C1	0.058 (4)	0.015 (3)	0.039 (3)	−0.002 (3)	−0.022 (3)	−0.005 (3)
C2	0.048 (4)	0.012 (3)	0.033 (3)	0.004 (3)	−0.018 (3)	−0.004 (2)
C3	0.050 (4)	0.019 (3)	0.037 (3)	0.000 (3)	−0.026 (3)	−0.001 (2)
C4	0.049 (4)	0.016 (3)	0.031 (3)	−0.001 (3)	−0.019 (3)	0.003 (2)
C5	0.050 (4)	0.018 (3)	0.042 (3)	−0.005 (3)	−0.028 (3)	0.001 (3)
C6	0.042 (4)	0.019 (3)	0.033 (3)	−0.005 (3)	−0.020 (3)	0.002 (2)
C7	0.041 (4)	0.018 (3)	0.032 (3)	0.003 (3)	−0.017 (3)	0.001 (2)
C8	0.053 (4)	0.020 (3)	0.041 (3)	−0.001 (3)	−0.031 (3)	0.000 (3)
C9	0.064 (4)	0.041 (4)	0.057 (4)	−0.012 (4)	0.016 (4)	−0.004 (3)
C10	0.078 (8)	0.078 (8)	0.089 (8)	−0.013 (7)	0.030 (7)	0.001 (7)
C11	0.096 (5)	0.094 (5)	0.105 (5)	0.003 (4)	0.020 (5)	−0.014 (4)
C12	0.121 (10)	0.116 (10)	0.123 (9)	0.003 (9)	0.021 (8)	−0.045 (8)
C13	0.099 (8)	0.118 (9)	0.126 (8)	0.012 (7)	0.026 (7)	−0.025 (7)
C14	0.127 (8)	0.134 (8)	0.132 (8)	0.011 (8)	0.038 (7)	−0.025 (7)
C15	0.162 (15)	0.164 (14)	0.132 (14)	0.006 (13)	−0.002 (12)	−0.015 (12)
O5A	0.069 (5)	0.036 (5)	0.054 (5)	−0.014 (5)	0.007 (5)	0.000 (4)
O6A	0.055 (5)	0.033 (5)	0.049 (5)	−0.009 (5)	0.005 (5)	−0.001 (5)
C9A	0.064 (5)	0.042 (4)	0.056 (4)	−0.013 (4)	0.012 (4)	−0.002 (4)
C10A	0.071 (10)	0.057 (9)	0.069 (9)	−0.009 (8)	0.019 (8)	0.002 (8)
O7A	0.089 (6)	0.085 (6)	0.098 (6)	0.007 (5)	0.022 (5)	−0.016 (5)
N1A	0.109 (6)	0.116 (6)	0.121 (6)	0.005 (6)	0.022 (6)	−0.012 (6)
C11A	0.097 (5)	0.098 (5)	0.108 (5)	0.005 (5)	0.020 (5)	−0.012 (5)
C12A	0.110 (9)	0.108 (9)	0.113 (9)	0.010 (8)	0.024 (8)	−0.021 (8)
C13A	0.100 (11)	0.108 (11)	0.119 (11)	0.008 (10)	0.020 (10)	−0.021 (10)
C14A	0.134 (13)	0.135 (13)	0.143 (12)	0.000 (12)	0.015 (11)	−0.023 (11)
C18	0.182 (15)	0.164 (14)	0.153 (14)	0.007 (13)	0.028 (13)	0.012 (12)
C16	0.140 (8)	0.143 (8)	0.118 (8)	0.003 (7)	0.014 (7)	0.001 (7)
N2	0.149 (9)	0.157 (9)	0.128 (8)	0.002 (7)	0.020 (7)	0.011 (7)
C17	0.168 (16)	0.178 (15)	0.129 (13)	0.024 (13)	0.015 (12)	0.016 (12)
O9	0.101 (11)	0.128 (13)	0.080 (9)	−0.038 (10)	−0.046 (8)	0.047 (9)

Geometric parameters (Å, º)

Eu1—O1	2.506 (4)	C12—H12C	0.9600
Eu1—O2	2.431 (4)	C13—H13A	0.9599
Eu1—O3^i	2.376 (4)	C13—H13B	0.9602
Eu1—O4^ii	2.359 (4)	C13—H13C	0.9601
Eu1—O5	2.469 (7)	C14—H14A	0.9601
Eu1—O6^iii	2.320 (13)	C14—H14B	0.9601
Eu1—O6	2.577 (7)	C14—H14C	0.9600
Eu1—O7	2.247 (8)	C15—H15A	0.9599
Eu1—O5A	2.493 (9)	C15—H15B	0.9599
Eu1—O6A	2.540 (9)	C15—H15C	0.9601
Eu1—O6A^iii	2.36 (3)	C15—C16	1.472 (9)
Eu1—O7A	2.393 (19)	O5A—C9A	1.235 (9)
O1—C1	1.256 (7)	O6A—C9A	1.225 (9)
O2—C1	1.248 (7)	C9A—C10A	1.59 (3)
O3—C8	1.262 (7)	C10A—H10D	0.9599
O4—C8	1.253 (7)	C10A—H10E	0.9599
O5—C9	1.260 (9)	C10A—H10F	0.9601
O6—C9	1.239 (8)	O7A—C11A	1.213 (10)
O7—C11	1.204 (8)	N1A—C11A	1.490 (9)
O8—C16	1.201 (9)	N1A—C13A	1.481 (10)
N1—C11	1.456 (9)	N1A—C14A	1.480 (10)
N1—C13	1.455 (9)	C11A—C12A	1.493 (10)
N1—C14	1.483 (9)	C12A—H12D	0.9599
C1—C2	1.496 (8)	C12A—H12E	0.9602
C2—C3	1.396 (8)	C12A—H12F	0.9600
C2—C7	1.385 (7)	C13A—H13D	0.9601
C3—H3	0.9300	C13A—H13E	0.9598
C3—C4	1.390 (8)	C13A—H13F	0.9601
C4—C4^iv	1.500 (11)	C14A—H14D	0.9601
C4—C5	1.390 (7)	C14A—H14E	0.9600
C5—H5	0.9300	C14A—H14F	0.9601
C5—C6	1.386 (8)	C18—H18A	0.9601
C6—C7	1.375 (8)	C18—H18B	0.9601
C6—C8	1.513 (7)	C18—H18C	0.9598
C7—H7	0.9300	C18—N2	1.449 (10)
C9—C10	1.551 (17)	C16—N2	1.439 (9)
C10—H10A	0.9599	N2—C17	1.451 (10)
C10—H10B	0.9601	C17—H17A	0.9599
C10—H10C	0.9599	C17—H17B	0.9600
C11—C12	1.481 (9)	C17—H17C	0.9599
C12—H12A	0.9600	O9—H9A	0.8500
C12—H12B	0.9600	O9—H9B	0.8502
O1—Eu1—O6	117.2 (5)	C9—C10—H10A	109.6
O1—Eu1—O6A	115.2 (11)	C9—C10—H10B	109.7
O2—Eu1—O1	52.55 (13)	C9—C10—H10C	109.1
O2—Eu1—O5	78.3 (3)	H10A—C10—H10B	109.5
O2—Eu1—O6	124.5 (4)	H10A—C10—H10C	109.5
O2—Eu1—O5A	74.7 (6)	H10B—C10—H10C	109.5
O2—Eu1—O6A	125.1 (7)	O7—C11—N1	117.9 (9)
O3^i—Eu1—O1	134.63 (15)	O7—C11—C12	127.5 (11)
O3^i—Eu1—O2	85.15 (14)	N1—C11—C12	114.7 (8)
O3^i—Eu1—O5	83.4 (4)	C11—C12—H12A	109.6
O3^i—Eu1—O6	70.7 (7)	C11—C12—H12B	109.4
O3^i—Eu1—O5A	74.7 (6)	C11—C12—H12C	109.4
O3^i—Eu1—O6A	73.3 (15)	H12A—C12—H12B	109.5
O3^i—Eu1—O7A	134.7 (6)	H12A—C12—H12C	109.5
O4^ii—Eu1—O1	80.04 (14)	H12B—C12—H12C	109.5
O4^ii—Eu1—O2	132.41 (14)	N1—C13—H13A	109.6
O4^ii—Eu1—O3^i	137.08 (15)	N1—C13—H13B	109.4
O4^ii—Eu1—O5	85.3 (3)	N1—C13—H13C	109.5
O4^ii—Eu1—O6	70.2 (7)	H13A—C13—H13B	109.5
O4^ii—Eu1—O5A	93.9 (6)	H13A—C13—H13C	109.5
O4^ii—Eu1—O6A^iii	76.7 (15)	H13B—C13—H13C	109.5
O4^ii—Eu1—O6A	67.8 (14)	N1—C14—H14A	109.7
O4^ii—Eu1—O7A	73.2 (6)	N1—C14—H14B	109.4
O5—Eu1—O1	73.5 (3)	N1—C14—H14C	109.4
O5—Eu1—O6	50.6 (2)	H14A—C14—H14B	109.5
O6^iii—Eu1—O1	146.6 (7)	H14A—C14—H14C	109.5
O6^iii—Eu1—O2	149.6 (6)	H14B—C14—H14C	109.5
O6^iii—Eu1—O3^i	78.4 (8)	H15A—C15—H15B	109.5
O6^iii—Eu1—O4^ii	74.3 (8)	H15A—C15—H15C	109.5
O6^iii—Eu1—O5	124.2 (4)	H15B—C15—H15C	109.5
O6^iii—Eu1—O6	73.6 (4)	C16—C15—H15A	109.2
O6^iii—Eu1—O6A^iii	3 (2)	C16—C15—H15B	109.7
O7—Eu1—O1	79.8 (3)	C16—C15—H15C	109.5
O7—Eu1—O2	84.9 (3)	C9A—O5A—Eu1	90.8 (6)
O7—Eu1—O3^i	115.9 (3)	Eu1^iii—O6A—Eu1	106.3 (9)
O7—Eu1—O4^ii	91.1 (3)	C9A—O6A—Eu1	88.8 (6)
O7—Eu1—O5	153.3 (4)	O5A—C9A—C10A	116 (2)
O7—Eu1—O6^iii	79.7 (4)	O6A—C9A—O5A	124.2 (11)
O7—Eu1—O6	150.6 (5)	O6A—C9A—C10A	119 (2)
O7—Eu1—O6A^iii	81.0 (5)	C9A—C10A—H10D	110.7
O5A—Eu1—O1	78.4 (7)	C9A—C10A—H10E	109.2
O5A—Eu1—O6A	51.2 (3)	C9A—C10A—H10F	108.6
O6A^iii—Eu1—O1	149.4 (15)	H10D—C10A—H10E	109.5
O6A^iii—Eu1—O2	147.9 (13)	H10D—C10A—H10F	109.5
O6A^iii—Eu1—O5A	122.6 (9)	H10E—C10A—H10F	109.5
O6A^iii—Eu1—O6A	73.7 (9)	C11A—O7A—Eu1	153.4 (15)
O6A^iii—Eu1—O7A	84.3 (11)	C13A—N1A—C11A	113.9 (10)
O7A—Eu1—O1	70.0 (6)	C14A—N1A—C11A	114.1 (10)
O7A—Eu1—O2	91.8 (6)	C14A—N1A—C13A	132.0 (15)
O7A—Eu1—O5A	147.3 (9)	O7A—C11A—N1A	115.3 (11)
O7A—Eu1—O6A	138.5 (13)	O7A—C11A—C12A	131.3 (16)
C1—O1—Eu1	90.9 (3)	N1A—C11A—C12A	113.5 (10)
C1—O2—Eu1	94.7 (3)	C11A—C12A—H12D	109.5
C8—O3—Eu1^v	133.3 (4)	C11A—C12A—H12E	109.4
C8—O4—Eu1^vi	139.9 (4)	C11A—C12A—H12F	109.5
C9—O5—Eu1	96.5 (6)	H12D—C12A—H12E	109.5
Eu1^iii—O6—Eu1	106.4 (4)	H12D—C12A—H12F	109.5
C9—O6—Eu1	91.9 (5)	H12E—C12A—H12F	109.5
C9—O6—Eu1^iii	160.7 (10)	N1A—C13A—H13D	109.6
C11—O7—Eu1	151.7 (7)	N1A—C13A—H13E	109.5
C11—N1—C14	108.0 (11)	N1A—C13A—H13F	109.3
C13—N1—C11	129.2 (11)	H13D—C13A—H13E	109.5
C13—N1—C14	122.8 (13)	H13D—C13A—H13F	109.5
O1—C1—C2	119.2 (5)	H13E—C13A—H13F	109.5
O2—C1—O1	121.7 (5)	N1A—C14A—H14D	109.5
O2—C1—C2	119.1 (5)	N1A—C14A—H14E	109.5
C3—C2—C1	121.3 (5)	N1A—C14A—H14F	109.4
C7—C2—C1	119.7 (5)	H14D—C14A—H14E	109.5
C7—C2—C3	119.1 (5)	H14D—C14A—H14F	109.5
C2—C3—H3	119.1	H14E—C14A—H14F	109.5
C4—C3—C2	121.8 (5)	H18A—C18—H18B	109.5
C4—C3—H3	119.1	H18A—C18—H18C	109.5
C3—C4—C4^iv	120.8 (6)	H18B—C18—H18C	109.5
C5—C4—C3	117.5 (5)	N2—C18—H18A	109.5
C5—C4—C4^iv	121.6 (7)	N2—C18—H18B	109.3
C4—C5—H5	119.3	N2—C18—H18C	109.5
C6—C5—C4	121.3 (5)	O8—C16—C15	121.9 (14)
C6—C5—H5	119.3	O8—C16—N2	120.2 (11)
C5—C6—C8	121.0 (5)	N2—C16—C15	117.9 (10)
C7—C6—C5	120.2 (5)	C18—N2—C17	118.8 (14)
C7—C6—C8	118.8 (5)	C16—N2—C18	121.0 (10)
C2—C7—H7	119.9	C16—N2—C17	120.2 (10)
C6—C7—C2	120.1 (5)	N2—C17—H17A	109.6
C6—C7—H7	119.9	N2—C17—H17B	109.5
O3—C8—C6	117.2 (5)	N2—C17—H17C	109.4
O4—C8—O3	126.6 (5)	H17A—C17—H17B	109.5
O4—C8—C6	116.3 (5)	H17A—C17—H17C	109.5
O5—C9—C10	122.7 (13)	H17B—C17—H17C	109.5
O6—C9—O5	119.5 (9)	H9A—O9—H9B	104.5
O6—C9—C10	117.8 (12)
Eu1—O1—C1—O2	−3.9 (8)	O8—C16—N2—C18	0.0 (3)
Eu1—O1—C1—C2	175.9 (6)	O8—C16—N2—C17	179.9 (3)
Eu1—O2—C1—O1	4.0 (8)	C1—C2—C3—C4	−178.0 (7)
Eu1—O2—C1—C2	−175.8 (6)	C1—C2—C7—C6	177.4 (6)
Eu1^v—O3—C8—O4	15.6 (13)	C2—C3—C4—C4^iv	179.1 (8)
Eu1^v—O3—C8—C6	−164.0 (5)	C2—C3—C4—C5	0.4 (11)
Eu1^vi—O4—C8—O3	4.0 (14)	C3—C2—C7—C6	−1.9 (10)
Eu1^vi—O4—C8—C6	−176.5 (5)	C3—C4—C5—C6	−1.5 (11)
Eu1—O5—C9—O6	13.2 (11)	C4^iv—C4—C5—C6	179.9 (8)
Eu1—O5—C9—C10	−166.8 (11)	C4—C5—C6—C7	0.9 (11)
Eu1^iii—O6—C9—O5	−174 (5)	C4—C5—C6—C8	−179.3 (7)
Eu1—O6—C9—O5	−12.5 (10)	C5—C6—C7—C2	0.8 (11)
Eu1^iii—O6—C9—C10	6 (5)	C5—C6—C8—O3	−2.6 (11)
Eu1—O6—C9—C10	167.4 (10)	C5—C6—C8—O4	177.8 (7)
Eu1—O7—C11—N1	117.8 (18)	C7—C2—C3—C4	1.3 (11)
Eu1—O7—C11—C12	−62.2 (18)	C7—C6—C8—O3	177.3 (7)
Eu1—O5A—C9A—O6A	−24 (3)	C7—C6—C8—O4	−2.3 (10)
Eu1—O5A—C9A—C10A	168 (2)	C8—C6—C7—C2	−179.0 (6)
Eu1—O6A—C9A—O5A	23 (3)	C13—N1—C11—O7	−179.9 (3)
Eu1^iii—O6A—C9A—O5A	−139 (13)	C13—N1—C11—C12	0.1 (4)
Eu1^iii—O6A—C9A—C10A	29 (15)	C14—N1—C11—O7	0.0 (3)
Eu1—O6A—C9A—C10A	−169 (3)	C14—N1—C11—C12	−180.0 (4)
Eu1—O7A—C11A—N1A	178 (3)	C15—C16—N2—C18	−180.0 (4)
Eu1—O7A—C11A—C12A	−2 (3)	C15—C16—N2—C17	0.0 (4)
O1—C1—C2—C3	−1.7 (11)	C13A—N1A—C11A—O7A	−179.8 (4)
O1—C1—C2—C7	179.1 (7)	C13A—N1A—C11A—C12A	0.3 (7)
O2—C1—C2—C3	178.1 (7)	C14A—N1A—C11A—O7A	−0.1 (7)
O2—C1—C2—C7	−1.1 (11)	C14A—N1A—C11A—C12A	179.9 (5)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C12—H12B···O5^vii	0.96	2.29	3.179 (19)	154
C15—H15A···O2	0.96	2.46	3.28 (2)	144
C13A—H13E···O2^viii	0.96	2.13	2.94 (3)	141
C14A—H14E···O5A^viii	0.96	1.83	2.71 (4)	150
O9—H9A···O2	0.85	2.50	2.947 (13)	114

Symmetry codes: (vii) x−1/2, −y+1/2, z+1/2; (viii) x−1, y, z.