An Eu-based metal–organic framework: poly[[tris­(μ4-benzene-1,4-dicarboxyl­ato)bis­(μ2-N,N-diethyl­formamide)dieuropium(III)] 0.7-hydrate]

Clausen, H.F.; Overgaard, J.; Poulsen, R.D.; Morgenroth, W.; Iversen, B.B.

doi:10.1107/S1600536806047143

An Eu-based metal–organic framework: poly[[tris(μ₄-benzene-1,4-dicarboxylato)bis(μ₂-N,N-diethylformamide)dieuropium(III)] 0.7-hydrate]

H. F. Clausen, J. Overgaard, R. D. Poulsen, W. Morgenroth and B. B. Iversen

The crystal structure of the title compound, {[Eu₂(C₈H₄O₄)₃(C₅H₁₁NO)₂]·0.7H₂O}_n, consists of chains formed by Eu atoms connected by the carboxylate groups of the benzene-1,4-dicarboxylate (BDC) linker. The chains are interconnected by BDC linkers, generating a three-dimensional framework with large voids. The Eu atoms are coordinated by seven carboxylate O atoms and one solvent O atom in a sterically constrained manner due to the carboxylate group rigidity, and this causes the coordination to be distorted dodecahedral. The ethyl groups of the solvent ligand are disordered in the void. The elongated Eu—O bond to the solvent indicates that it is loosely bound to the framework, and hence solvent exchange may be possible. In the void there is additionally one partly occupied disordered water molecule.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047143/lh2226sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047143/lh2226Isup2.hkl Contains datablock I

CCDC reference: 630052

checkCIF report

Key indicators

Single-crystal synchrotron study
T = 100 K
Mean (C-C) = 0.002 Å
H-atom completeness 97%
Disorder in main residue
R factor = 0.037
wR factor = 0.090
Data-to-parameter ratio = 76.9

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT220_ALERT_2_A Large Non-Solvent    C     Ueq(max)/Ueq(min) ...      10.00 Ratio

Author Response: The DEF molecule is only loosely attached to the framework and is placed in large voids, which makes it prone to significant thermal motion and disorder.

PLAT222_ALERT_3_A Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       9.39 Ratio

Author Response: The DEF molecule is only loosely attached to the framework and is placed in large voids, which makes it prone to significant thermal motion and disorder.


Alert level B
PLAT432_ALERT_2_B Short Inter X...Y Contact  C19B   ..  O99     ..       2.73 Ang.

Author Response: There is a hydrogen bond between C19B-H19D and O99, with a hydrogen bond length of 2.01 \%A. Note =99 is part of a disordered water molecule.


Alert level C
RINTA01_ALERT_3_C  The value of Rint is greater than 0.10
            Rint given   0.126

Author Response: The data set consists of 22166 unique reflections measured in average 18.9 times. This huge redundancy leads to a high internal R-value.

PLAT020_ALERT_3_C The value of Rint is greater than 0.10 .........       0.13

Author Response: The data set consists of 22166 unique reflections measured in average 18.9 times. This huge redundancy leads to a high internal R-value.

PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98

Author Response: The experimental setup was geometrically limited at the synchrotron source, hence it did not give full coverage.

PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?

Author Response: The reported SumFormula is correct, as the void is occupied by a disordered water molecule and not a oxygen molecule. However the disordered hydrogen atoms could not be found.

PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?

Author Response: The moiety formula reported is correct, as the void is occupied by a disordered water molecule and not a oxygen molecule.

PLAT213_ALERT_2_C Atom O9      has ADP max/min Ratio .............       3.40 prola

Author Response: This might be due to unresolved disorder.

PLAT213_ALERT_2_C Atom C19B    has ADP max/min Ratio .............       3.70 prola

Author Response: This might be due to unresolved disorder.

PLAT220_ALERT_2_C Large Non-Solvent    O     Ueq(max)/Ueq(min) ...       3.50 Ratio

Author Response: The DEF molecule is only loosely attached to the framework and is placed in large voids, which makes it prone to significant thermal motion and disorder.

PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C15

Author Response: Disordered solvent molecule.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C16B

Author Response: Disordered solvent molecule.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C17B

Author Response: Disordered solvent molecule.

PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for       C16A

Author Response: Disordered solvent molecule.

PLAT301_ALERT_3_C Main Residue  Disorder .........................      13.00 Perc.

Author Response: Disordered solvent molecules.

PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      35.00 Perc.

Author Response: Disordered solvent molecules.


Alert level G
FORMU01_ALERT_2_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and the formula from the _atom_site* data.
            Atom count from _chemical_formula_sum:C17 H17.7 Eu1 N1 O7.35
            Atom count from the _atom_site data:  C17 H17 Eu1 N1 O7.35
  ABSMU_01  Radiation type not identified. Calculation of
            _exptl_absorpt_correction_mu not performed.

Author Response: The hydrogen atoms of the water molecule could not be found, hence the _chemical_formula_sum differ from the formula from the _atom_site* data.

CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.

Author Response: The hydrogen atoms of the water molecule could not be found, hence there is a difference between formula and atom_site contents detected. Therefore it is intentional that these atoms are missing in the atom site list.

CELLZ01_ALERT_1_G WARNING: H atoms missing from atom site list. Is this intentional?
           From the CIF: _cell_formula_units_Z    8
           From the CIF: _chemical_formula_sum  C17 H17.7 Eu N O7.35
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        136.00    136.00    0.00
           H        141.60    136.00    5.60
           Eu         8.00      8.00    0.00
           N          8.00      8.00    0.00
           O         58.80     58.80    0.00


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

   4 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
   5 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

Computing details top

Data collection: program (reference)?; cell refinement: XDS2004; data reduction: XDS2004 (Kabsch, 1993); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XSHELL (Version 4.02); software used to prepare material for publication: enCIFer (Version 1.2; Allen et al., 2004).

poly[[tris(µ₄-benzene-1,4-dicarboxylato)bis(µ₂-N,N- diethylformamide)dieuropium(III)] 0.7-hydrate] top

Crystal data top

[Eu₂(C₈H₄O₄)₃(C₅H₁₁NO)₂]·0.7H₂O	F(000) = 1982
M_r = 505.08	D_x = 1.831 Mg m⁻³
Monoclinic, C2/c	Synchrotron radiation, λ = 0.55000 Å
Hall symbol: -C 2yc	Cell parameters from 57266 reflections
a = 18.010 (7) Å	θ = 1.7–38.8°
b = 11.478 (7) Å	µ = 1.63 mm⁻¹
c = 18.743 (12) Å	T = 100 K
β = 108.91 (3)°	Rectuangular, white
V = 3665 (4) Å³	0.10 × 0.10 × 0.08 mm
Z = 8

Data collection top

Huber four-circle diffractometer	19344 reflections with I > 2σ(I)
Radiation source: D3, Hasylab, Hamburg	R_int = 0.126
Double crystal Si 111 monochr monochromator	θ_max = 38.8°, θ_min = 1.7°
Detector resolution: 12.65 pixels mm^-1	h = 0→40
φ scans	k = 0→25
424451 measured reflections	l = −42→39
22159 independent reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.090	w = 1/[σ²(F_o²) + (0.0449P)² + 7.3908P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max = 0.011
22159 reflections	Δρ_max = 3.47 e Å⁻³
288 parameters	Δρ_min = −3.26 e Å⁻³
13 restraints	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.00453 (17)

Special details top

Experimental. A correction for the oblique incidence of the X-ray beam through the detector has been made using a transmission factor of 0.37 for the MarCCD detector measured at a wavelength of 0.55 Å.

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
Eu1	0.498091 (3)	0.058967 (4)	0.898036 (3)	0.00696 (1)
O1	0.40982 (7)	0.05628 (11)	0.77564 (6)	0.01829 (19)
O2	0.58662 (5)	0.01120 (9)	0.83855 (5)	0.01167 (11)
O8	0.56978 (8)	0.17803 (12)	0.99946 (6)	0.0222 (2)
O9	0.42636 (12)	−0.11407 (17)	0.88661 (7)	0.0408 (5)
O11	0.39304 (7)	0.18172 (11)	0.90617 (6)	0.01712 (16)
O12	0.42060 (7)	0.06532 (11)	1.00488 (8)	0.0209 (2)
O15	0.52735 (8)	0.24314 (10)	0.84810 (7)	0.01913 (17)
N15	0.55747 (17)	0.43506 (14)	0.86723 (17)	0.0381 (5)
C1	0.38204 (6)	0.05873 (10)	0.70580 (6)	0.01068 (13)
C2	0.80553 (7)	0.37928 (11)	1.17100 (6)	0.01217 (14)
C3	0.77018 (9)	0.32070 (15)	1.21686 (7)	0.0185 (2)
H3	0.7924	0.3242	1.2690	0.022*
C4	0.70182 (12)	0.25721 (18)	1.18462 (7)	0.0256 (4)
H4	0.6785	0.2180	1.2152	0.031*
C5	0.66815 (11)	0.25224 (15)	1.10620 (7)	0.0222 (3)
C6	0.70235 (9)	0.31309 (13)	1.06052 (7)	0.0182 (2)
H6	0.6791	0.3116	1.0084	0.022*
C7	0.77102 (8)	0.37592 (13)	1.09267 (6)	0.01507 (18)
H7	0.7940	0.4158	1.0620	0.018*
C8	0.59804 (13)	0.17659 (17)	1.07025 (8)	0.0267 (4)
C11	0.37941 (7)	0.14514 (13)	0.96395 (8)	0.01517 (18)
C12	0.31243 (8)	0.19848 (13)	0.98321 (8)	0.01555 (19)
C13	0.30288 (9)	0.17871 (14)	1.05310 (8)	0.0187 (2)
H13	0.3381	0.1314	1.0885	0.022*
C14	0.25960 (9)	0.26990 (15)	0.93044 (8)	0.0204 (3)
H14	0.2662	0.2832	0.8839	0.024*
C15	0.5187 (2)	0.33910 (18)	0.8711 (2)	0.0492 (9)
H15	0.4804	0.3459	0.8942	0.059*
C16A	0.6342 (3)	0.4262 (4)	0.8584 (4)	0.0350 (10)	0.475 (3)
H16A	0.6457	0.3446	0.8534	0.042*	0.475 (3)
H16B	0.6731	0.4555	0.9038	0.042*	0.475 (3)
C18A	0.6420 (7)	0.4906 (12)	0.7926 (7)	0.086 (4)	0.475 (3)
H18A	0.6102	0.4539	0.7469	0.129*	0.475 (3)
H18B	0.6959	0.4899	0.7944	0.129*	0.475 (3)
H18C	0.6250	0.5696	0.7939	0.129*	0.475 (3)
C16B	0.6014 (3)	0.4414 (3)	0.8133 (3)	0.0299 (8)	0.525 (3)
H16C	0.5774	0.5005	0.7760	0.036*	0.525 (3)
H16D	0.5959	0.3674	0.7871	0.036*	0.525 (3)
C18B	0.6870 (4)	0.4684 (8)	0.8469 (6)	0.060 (2)	0.525 (3)
H18D	0.6934	0.5436	0.8706	0.089*	0.525 (3)
H18E	0.7108	0.4686	0.8079	0.089*	0.525 (3)
H18F	0.7118	0.4103	0.8838	0.089*	0.525 (3)
C17A	0.5233 (3)	0.5452 (3)	0.8816 (3)	0.0303 (9)	0.475 (3)
H17A	0.4677	0.5358	0.8740	0.036*	0.475 (3)
H17B	0.5298	0.6057	0.8480	0.036*	0.475 (3)
C19A	0.5668 (4)	0.5764 (6)	0.9623 (4)	0.052 (2)	0.475 (3)
H19A	0.5619	0.5140	0.9946	0.078*	0.475 (3)
H19B	0.5450	0.6463	0.9754	0.078*	0.475 (3)
H19C	0.6212	0.5887	0.9684	0.078*	0.475 (3)
C17B	0.5679 (4)	0.5393 (4)	0.9200 (5)	0.0542 (19)	0.525 (3)
H17C	0.5557	0.5166	0.9648	0.065*	0.525 (3)
H17D	0.6220	0.5653	0.9355	0.065*	0.525 (3)
C19B	0.5152 (6)	0.6364 (6)	0.8812 (8)	0.113 (5)	0.525 (3)
H19D	0.5272	0.6585	0.8368	0.169*	0.525 (3)
H19E	0.5228	0.7019	0.9146	0.169*	0.525 (3)
H19F	0.4615	0.6112	0.8672	0.169*	0.525 (3)
O99	0.4752 (5)	0.7751 (5)	0.7560 (4)	0.047 (2)	0.350 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.00569 (2)	0.00944 (2)	0.00551 (2)	0.00041 (1)	0.00151 (1)	−0.00021 (1)
O1	0.0123 (3)	0.0333 (6)	0.0073 (3)	0.0056 (3)	0.0004 (2)	−0.0010 (3)
O2	0.0094 (2)	0.0166 (3)	0.0099 (2)	0.0020 (2)	0.0044 (2)	0.0015 (2)
O8	0.0301 (5)	0.0240 (5)	0.0087 (3)	−0.0159 (4)	0.0012 (3)	−0.0021 (3)
O9	0.0594 (11)	0.0475 (9)	0.0106 (4)	−0.0440 (9)	0.0045 (5)	−0.0021 (4)
O11	0.0174 (4)	0.0221 (4)	0.0154 (3)	0.0096 (3)	0.0102 (3)	0.0065 (3)
O12	0.0170 (4)	0.0248 (5)	0.0248 (5)	0.0137 (3)	0.0121 (4)	0.0136 (4)
O15	0.0264 (5)	0.0158 (4)	0.0162 (4)	−0.0012 (3)	0.0082 (4)	0.0027 (3)
N15	0.0541 (14)	0.0132 (5)	0.0595 (15)	0.0017 (6)	0.0359 (13)	0.0027 (6)
C1	0.0083 (3)	0.0158 (4)	0.0074 (3)	−0.0003 (3)	0.0017 (2)	−0.0005 (3)
C2	0.0135 (4)	0.0150 (4)	0.0071 (3)	−0.0028 (3)	0.0020 (3)	−0.0006 (3)
C3	0.0218 (5)	0.0251 (6)	0.0072 (3)	−0.0123 (4)	0.0027 (3)	−0.0010 (3)
C4	0.0331 (8)	0.0334 (8)	0.0080 (4)	−0.0228 (7)	0.0033 (4)	−0.0012 (4)
C5	0.0306 (7)	0.0247 (6)	0.0083 (3)	−0.0182 (5)	0.0021 (4)	−0.0021 (4)
C6	0.0235 (5)	0.0211 (5)	0.0072 (3)	−0.0113 (4)	0.0012 (3)	−0.0009 (3)
C7	0.0171 (4)	0.0193 (5)	0.0076 (3)	−0.0062 (4)	0.0024 (3)	−0.0001 (3)
C8	0.0383 (8)	0.0293 (7)	0.0089 (4)	−0.0247 (7)	0.0025 (4)	−0.0021 (4)
C11	0.0132 (4)	0.0191 (5)	0.0164 (4)	0.0092 (3)	0.0092 (3)	0.0069 (3)
C12	0.0139 (4)	0.0200 (5)	0.0161 (4)	0.0099 (3)	0.0094 (3)	0.0082 (4)
C13	0.0177 (5)	0.0249 (6)	0.0168 (4)	0.0139 (4)	0.0103 (4)	0.0105 (4)
C14	0.0198 (5)	0.0288 (6)	0.0171 (5)	0.0160 (5)	0.0122 (4)	0.0118 (4)
C15	0.0695 (19)	0.0140 (6)	0.093 (2)	0.0074 (8)	0.066 (2)	0.0081 (9)
C16A	0.042 (3)	0.0231 (17)	0.046 (3)	−0.0012 (16)	0.023 (2)	0.0059 (17)
C18A	0.084 (7)	0.101 (9)	0.096 (8)	0.027 (6)	0.062 (7)	0.064 (7)
C16B	0.0315 (18)	0.0223 (13)	0.037 (2)	−0.0065 (11)	0.0122 (16)	0.0090 (12)
C18B	0.034 (3)	0.058 (4)	0.082 (6)	−0.008 (3)	0.012 (3)	0.005 (4)
C17A	0.033 (2)	0.0117 (11)	0.045 (3)	0.0007 (11)	0.0108 (19)	−0.0031 (12)
C19A	0.046 (3)	0.035 (3)	0.070 (5)	−0.004 (2)	0.012 (3)	−0.032 (3)
C17B	0.054 (4)	0.0226 (17)	0.089 (6)	−0.009 (2)	0.027 (4)	−0.022 (3)
C19B	0.059 (4)	0.040 (3)	0.183 (12)	0.020 (3)	−0.039 (6)	−0.055 (5)
O99	0.083 (6)	0.027 (2)	0.039 (3)	−0.005 (3)	0.030 (3)	0.003 (2)

Geometric parameters (Å, º) top

Eu1—O2	2.2888 (12)	C11—C12	1.4976 (16)
Eu1—O1	2.3295 (18)	C12—C13	1.3940 (19)
Eu1—O9	2.3410 (17)	C12—C14	1.3948 (18)
Eu1—O8	2.3574 (15)	C13—C14^iv	1.3907 (18)
Eu1—O12ⁱ	2.4007 (15)	C13—H13	0.9300
Eu1—O11	2.4031 (12)	C14—H14	0.9300
Eu1—O15	2.4376 (16)	C15—H15	0.9300
Eu1—O12	2.7884 (18)	C16A—C18A	1.483 (7)
Eu1—Eu1ⁱ	4.034 (2)	C16A—H16A	0.9700
O1—C1	1.2410 (17)	C16A—H16B	0.9700
O2—C1ⁱⁱ	1.2694 (15)	C18A—H18A	0.9600
O8—C8	1.2577 (19)	C18A—H18B	0.9600
O9—C8ⁱ	1.262 (2)	C18A—H18C	0.9600
O11—C11	1.2576 (17)	C16B—C18B	1.497 (6)
O12—C11	1.2686 (16)	C16B—H16C	0.9700
O15—C15	1.211 (3)	C16B—H16D	0.9700
N15—C15	1.318 (3)	C18B—H18D	0.9600
N15—C16A	1.448 (5)	C18B—H18E	0.9600
N15—C17A	1.469 (4)	C18B—H18F	0.9600
N15—C16B	1.473 (5)	C17A—C19A	1.503 (7)
N15—C17B	1.524 (5)	C17A—H17A	0.9700
C1—C2ⁱⁱⁱ	1.4991 (17)	C17A—H17B	0.9700
C2—C3	1.3968 (18)	C19A—H19A	0.9600
C2—C7	1.3971 (18)	C19A—H19B	0.9600
C3—C4	1.389 (2)	C19A—H19C	0.9600
C3—H3	0.9300	C17B—C19B	1.491 (7)
C4—C5	1.398 (2)	C17B—H17C	0.9700
C4—H4	0.9300	C17B—H17D	0.9700
C5—C6	1.394 (2)	C19B—H19D	0.9600
C5—C8	1.500 (2)	C19B—H19E	0.9600
C6—C7	1.3891 (19)	C19B—H19F	0.9600
C6—H6	0.9300	O99—O99ⁱⁱ	0.987 (15)
C7—H7	0.9300

O2—Eu1—O1	82.99 (5)	C7—C2—C1^v	120.23 (11)
O2—Eu1—O9	101.72 (7)	C4—C3—C2	120.09 (12)
O1—Eu1—O9	73.65 (5)	C4—C3—H3	120.0
O2—Eu1—O8	104.23 (6)	C2—C3—H3	120.0
O1—Eu1—O8	145.32 (5)	C3—C4—C5	120.01 (13)
O9—Eu1—O8	135.02 (5)	C3—C4—H4	120.0
O2—Eu1—O12ⁱ	82.92 (5)	C5—C4—H4	120.0
O1—Eu1—O12ⁱ	142.42 (5)	C6—C5—C4	119.87 (13)
O9—Eu1—O12ⁱ	75.41 (7)	C6—C5—C8	119.30 (12)
O8—Eu1—O12ⁱ	72.13 (7)	C4—C5—C8	120.74 (13)
O2—Eu1—O11	149.14 (4)	C7—C6—C5	120.16 (12)
O1—Eu1—O11	76.72 (5)	C7—C6—H6	119.9
O9—Eu1—O11	94.63 (8)	C5—C6—H6	119.9
O8—Eu1—O11	81.12 (6)	C6—C7—C2	120.03 (12)
O12ⁱ—Eu1—O11	126.85 (5)	C6—C7—H7	120.0
O2—Eu1—O15	75.48 (5)	C2—C7—H7	120.0
O1—Eu1—O15	78.28 (5)	O8—C8—O9ⁱ	125.27 (14)
O9—Eu1—O15	151.91 (5)	O8—C8—C5	117.40 (13)
O8—Eu1—O15	71.14 (6)	O9ⁱ—C8—C5	117.29 (13)
O12ⁱ—Eu1—O15	130.67 (5)	O11—C11—O12	121.52 (11)
O11—Eu1—O15	77.79 (5)	O11—C11—C12	117.92 (11)
O2—Eu1—O12	161.08 (3)	O12—C11—C12	120.56 (12)
O1—Eu1—O12	111.53 (6)	O11—C11—Eu1	51.98 (7)
O9—Eu1—O12	72.42 (6)	O12—C11—Eu1	69.62 (8)
O8—Eu1—O12	71.12 (6)	C12—C11—Eu1	169.41 (9)
O12ⁱ—Eu1—O12	78.20 (5)	C13—C12—C14	119.90 (11)
O11—Eu1—O12	49.57 (4)	C13—C12—C11	120.95 (11)
O15—Eu1—O12	118.29 (4)	C14—C12—C11	119.15 (11)
O2—Eu1—C11	173.39 (3)	C14^iv—C13—C12	119.64 (11)
O1—Eu1—C11	93.48 (6)	C14^iv—C13—H13	120.2
O9—Eu1—C11	82.54 (7)	C12—C13—H13	120.2
O8—Eu1—C11	75.57 (6)	C13^iv—C14—C12	120.46 (12)
O12ⁱ—Eu1—C11	103.15 (5)	C13^iv—C14—H14	119.8
O11—Eu1—C11	24.35 (4)	C12—C14—H14	119.8
O15—Eu1—C11	98.37 (5)	O15—C15—N15	127.5 (2)
O12—Eu1—C11	25.24 (3)	O15—C15—H15	116.3
O2—Eu1—Eu1ⁱ	125.49 (4)	N15—C15—H15	116.3
O1—Eu1—Eu1ⁱ	136.48 (4)	N15—C16A—C18A	114.3 (6)
O9—Eu1—Eu1ⁱ	68.99 (4)	N15—C16A—H16A	108.7
O8—Eu1—Eu1ⁱ	66.04 (5)	C18A—C16A—H16A	108.7
O12ⁱ—Eu1—Eu1ⁱ	42.57 (4)	N15—C16A—H16B	108.7
O11—Eu1—Eu1ⁱ	84.76 (4)	C18A—C16A—H16B	108.7
O15—Eu1—Eu1ⁱ	135.67 (3)	H16A—C16A—H16B	107.6
O12—Eu1—Eu1ⁱ	35.63 (3)	C16A—C18A—H18A	109.5
C11—Eu1—Eu1ⁱ	60.67 (4)	C16A—C18A—H18B	109.5
C1—O1—Eu1	162.10 (10)	H18A—C18A—H18B	109.5
C1ⁱⁱ—O2—Eu1	138.06 (9)	C16A—C18A—H18C	109.5
C8—O8—Eu1	140.50 (11)	H18A—C18A—H18C	109.5
C8ⁱ—O9—Eu1	136.09 (11)	H18B—C18A—H18C	109.5
C11—O11—Eu1	103.67 (8)	N15—C16B—C18B	115.5 (5)
C11—O12—Eu1ⁱ	168.82 (13)	N15—C16B—H16C	108.4
C11—O12—Eu1	85.14 (9)	C18B—C16B—H16C	108.4
Eu1ⁱ—O12—Eu1	101.80 (5)	N15—C16B—H16D	108.4
C15—O15—Eu1	125.67 (15)	C18B—C16B—H16D	108.4
C15—N15—C16A	119.3 (3)	H16C—C16B—H16D	107.5
C15—N15—C17A	116.6 (3)	N15—C17A—C19A	106.1 (4)
C16A—N15—C17A	123.6 (3)	N15—C17A—H17A	110.5
C15—N15—C16B	119.4 (2)	C19A—C17A—H17A	110.5
C17A—N15—C16B	115.7 (3)	N15—C17A—H17B	110.5
C15—N15—C17B	125.2 (4)	C19A—C17A—H17B	110.5
C16A—N15—C17B	102.0 (4)	H17A—C17A—H17B	108.7
C16B—N15—C17B	115.2 (4)	C19B—C17B—N15	110.2 (6)
O1—C1—O2ⁱⁱ	124.61 (12)	C19B—C17B—H17C	109.6
O1—C1—C2ⁱⁱⁱ	117.99 (11)	N15—C17B—H17C	109.6
O2ⁱⁱ—C1—C2ⁱⁱⁱ	117.40 (10)	C19B—C17B—H17D	109.6
C3—C2—C7	119.81 (11)	N15—C17B—H17D	109.6
C3—C2—C1^v	119.91 (10)	H17C—C17B—H17D	108.1

O2—Eu1—O1—C1	−20.5 (3)	C3—C4—C5—C6	−1.4 (3)
O9—Eu1—O1—C1	−124.9 (3)	C3—C4—C5—C8	175.1 (2)
O8—Eu1—O1—C1	84.5 (3)	C4—C5—C6—C7	1.8 (3)
O12ⁱ—Eu1—O1—C1	−89.2 (3)	C8—C5—C6—C7	−174.71 (18)
O11—Eu1—O1—C1	136.1 (3)	C5—C6—C7—C2	−0.7 (3)
O15—Eu1—O1—C1	56.1 (3)	C3—C2—C7—C6	−0.9 (2)
O12—Eu1—O1—C1	172.1 (3)	C1^v—C2—C7—C6	176.51 (14)
C11—Eu1—O1—C1	153.9 (3)	Eu1—O8—C8—O9ⁱ	−24.6 (4)
Eu1ⁱ—Eu1—O1—C1	−156.5 (3)	Eu1—O8—C8—C5	153.16 (16)
O1—Eu1—O2—C1ⁱⁱ	68.61 (12)	C6—C5—C8—O8	−4.9 (3)
O9—Eu1—O2—C1ⁱⁱ	140.24 (12)	C4—C5—C8—O8	178.6 (2)
O8—Eu1—O2—C1ⁱⁱ	−76.84 (13)	C6—C5—C8—O9ⁱ	173.1 (2)
O12ⁱ—Eu1—O2—C1ⁱⁱ	−146.32 (12)	C4—C5—C8—O9ⁱ	−3.4 (4)
O11—Eu1—O2—C1ⁱⁱ	19.70 (16)	Eu1—O11—C11—O12	3.61 (19)
O15—Eu1—O2—C1ⁱⁱ	−11.05 (12)	Eu1—O11—C11—C12	−176.16 (12)
O12—Eu1—O2—C1ⁱⁱ	−150.00 (13)	Eu1ⁱ—O12—C11—O11	125.9 (5)
Eu1ⁱ—Eu1—O2—C1ⁱⁱ	−147.33 (10)	Eu1—O12—C11—O11	−3.03 (16)
O2—Eu1—O8—C8	−110.2 (2)	Eu1ⁱ—O12—C11—C12	−54.4 (6)
O1—Eu1—O8—C8	151.4 (2)	Eu1—O12—C11—C12	176.73 (14)
O9—Eu1—O8—C8	13.1 (3)	Eu1ⁱ—O12—C11—Eu1	128.9 (6)
O12ⁱ—Eu1—O8—C8	−32.7 (2)	O1—Eu1—C11—O11	−46.15 (11)
O11—Eu1—O8—C8	100.8 (2)	O9—Eu1—C11—O11	−119.14 (12)
O15—Eu1—O8—C8	−179.2 (3)	O8—Eu1—C11—O11	100.47 (12)
O12—Eu1—O8—C8	50.6 (2)	O12ⁱ—Eu1—C11—O11	167.80 (11)
C11—Eu1—O8—C8	76.6 (2)	O15—Eu1—C11—O11	32.50 (11)
Eu1ⁱ—Eu1—O8—C8	12.6 (2)	O12—Eu1—C11—O11	176.72 (17)
O2—Eu1—O9—C8ⁱ	134.0 (3)	Eu1ⁱ—Eu1—C11—O11	170.81 (12)
O1—Eu1—O9—C8ⁱ	−147.0 (3)	O1—Eu1—C11—O12	137.13 (11)
O8—Eu1—O9—C8ⁱ	9.8 (3)	O9—Eu1—C11—O12	64.14 (12)
O12ⁱ—Eu1—O9—C8ⁱ	54.6 (3)	O8—Eu1—C11—O12	−76.25 (11)
O11—Eu1—O9—C8ⁱ	−72.3 (3)	O12ⁱ—Eu1—C11—O12	−8.92 (14)
O15—Eu1—O9—C8ⁱ	−144.9 (2)	O11—Eu1—C11—O12	−176.72 (18)
O12—Eu1—O9—C8ⁱ	−27.4 (3)	O15—Eu1—C11—O12	−144.22 (11)
C11—Eu1—O9—C8ⁱ	−51.1 (3)	Eu1ⁱ—Eu1—C11—O12	−5.91 (9)
Eu1ⁱ—Eu1—O9—C8ⁱ	10.3 (3)	O1—Eu1—C11—C12	−27.4 (6)
O2—Eu1—O11—C11	−177.47 (9)	O9—Eu1—C11—C12	−100.4 (6)
O1—Eu1—O11—C11	132.31 (12)	O8—Eu1—C11—C12	119.2 (6)
O9—Eu1—O11—C11	60.32 (11)	O12ⁱ—Eu1—C11—C12	−173.4 (6)
O8—Eu1—O11—C11	−74.56 (12)	O11—Eu1—C11—C12	18.8 (6)
O12ⁱ—Eu1—O11—C11	−14.90 (13)	O15—Eu1—C11—C12	51.3 (6)
O15—Eu1—O11—C11	−147.05 (11)	O12—Eu1—C11—C12	−164.5 (7)
O12—Eu1—O11—C11	−1.84 (10)	Eu1ⁱ—Eu1—C11—C12	−170.4 (6)
Eu1ⁱ—Eu1—O11—C11	−8.04 (10)	O11—C11—C12—C13	−167.81 (16)
O2—Eu1—O12—C11	174.86 (11)	O12—C11—C12—C13	12.4 (3)
O1—Eu1—O12—C11	−46.88 (12)	Eu1—C11—C12—C13	175.5 (5)
O9—Eu1—O12—C11	−110.63 (13)	O11—C11—C12—C14	11.5 (2)
O8—Eu1—O12—C11	96.19 (12)	O12—C11—C12—C14	−168.30 (17)
O12ⁱ—Eu1—O12—C11	171.13 (14)	Eu1—C11—C12—C14	−5.2 (7)
O11—Eu1—O12—C11	1.78 (10)	C14—C12—C13—C14^iv	0.3 (3)
O15—Eu1—O12—C11	41.07 (12)	C11—C12—C13—C14^iv	179.55 (17)
Eu1ⁱ—Eu1—O12—C11	171.13 (14)	C13—C12—C14—C13^iv	−0.3 (3)
O2—Eu1—O12—Eu1ⁱ	3.73 (16)	C11—C12—C14—C13^iv	−179.56 (17)
O1—Eu1—O12—Eu1ⁱ	141.99 (6)	Eu1—O15—C15—N15	153.1 (3)
O9—Eu1—O12—Eu1ⁱ	78.24 (8)	C16A—N15—C15—O15	−22.3 (7)
O8—Eu1—O12—Eu1ⁱ	−74.94 (8)	C17A—N15—C15—O15	165.0 (4)
O12ⁱ—Eu1—O12—Eu1ⁱ	0.0	C16B—N15—C15—O15	18.0 (6)
O11—Eu1—O12—Eu1ⁱ	−169.35 (8)	C17B—N15—C15—O15	−155.7 (5)
O15—Eu1—O12—Eu1ⁱ	−130.06 (5)	C15—N15—C16A—C18A	125.0 (8)
C11—Eu1—O12—Eu1ⁱ	−171.13 (14)	C17A—N15—C16A—C18A	−62.9 (10)
O2—Eu1—O15—C15	−157.7 (3)	C16B—N15—C16A—C18A	24.7 (8)
O1—Eu1—O15—C15	116.6 (3)	C17B—N15—C16A—C18A	−92.4 (9)
O9—Eu1—O15—C15	114.6 (3)	C15—N15—C16B—C18B	−123.1 (5)
O8—Eu1—O15—C15	−46.8 (3)	C16A—N15—C16B—C18B	−23.0 (6)
O12ⁱ—Eu1—O15—C15	−90.7 (3)	C17A—N15—C16B—C18B	89.5 (6)
O11—Eu1—O15—C15	37.9 (3)	C17B—N15—C16B—C18B	51.2 (6)
O12—Eu1—O15—C15	8.3 (3)	C15—N15—C17A—C19A	98.8 (6)
C11—Eu1—O15—C15	24.7 (3)	C16A—N15—C17A—C19A	−73.5 (6)
Eu1ⁱ—Eu1—O15—C15	−31.3 (3)	C16B—N15—C17A—C19A	−113.0 (5)
Eu1—O1—C1—O2ⁱⁱ	39.1 (4)	C17B—N15—C17A—C19A	−15.3 (7)
Eu1—O1—C1—C2ⁱⁱⁱ	−141.8 (3)	C15—N15—C17B—C19B	−104.2 (8)
C7—C2—C3—C4	1.4 (3)	C16A—N15—C17B—C19B	116.2 (8)
C1^v—C2—C3—C4	−176.05 (17)	C17A—N15—C17B—C19B	−17.4 (8)
C2—C3—C4—C5	−0.2 (3)	C16B—N15—C17B—C19B	81.9 (9)

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

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An Eu-based metal–organic framework: poly[[tris­(μ4-benzene-1,4-dicarboxyl­ato)bis­(μ2-N,N-diethyl­formamide)dieuropium(III)] 0.7-hydrate]

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An Eu-based metal–organic framework: poly[[tris(μ₄-benzene-1,4-dicarboxylato)bis(μ₂-N,N-diethylformamide)dieuropium(III)] 0.7-hydrate]