Di-μ-benzoato-κO,O':O';κO:O,O'-bis[aqua-bis-(benzoato-κO,O')(dimethylformamide-κO)europium(III)].

The title dimeric complex, [Eu(2)(C(7)H(5)O(2))(6)(C(3)H(7)NO)(2)(H(2)O)(2)], is centrosymmetric, implying that pairs of equivalent Eu(3+) ions and ligands lie trans to each other and that the two Eu(3+) ions have exactly the same coordination environment. Each Eu(3+) ion is nine-coordinated by two bidentate benzoate ligands, two bridging tridentate chelating benzoate ligands, and one dimethylformamide and one water molecule. The coordination polyhedron of each Eu(3+) ion can be described with a distorted monocapped square-anti-prismatic geometry. The mol-ecular structure is stabilized by intra- and inter-molecular hydrogen bonds between the water mol-ecules and benzoate O atoms.

Related literature

For properties of rare earth compounds derived from carboxylic acids, see: Chin et al. (1994 ▶); Singh et al. (2002 ▶). For related compounds, see: Jin et al. (1996 ▶); Gubina et al. (2000 ▶); Wang et al. (2003 ▶); Qiu et al. (2007 ▶); Ooi et al. (2010 ▶).

Experimental

Crystal data

[Eu2(C7H5O2)6(C3H7NO)2(H2O)2]

M = 1212.80

Monoclinic,

a = 11.6395 (2) Å

b = 8.3692 (1) Å

c = 25.5235 (4) Å

β = 101.460 (2)°

V = 2436.76 (6) Å3

Z = 2

Cu Kα radiation

μ = 18.84 mm−1

T = 291 K

0.36 × 0.32 × 0.32 mm

Data collection

Oxford Gemini S Ultra diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.056, T max = 0.065

8782 measured reflections

4294 independent reflections

3860 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.120

S = 1.03

4294 reflections

315 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.20 e Å−3

Δρmin = −1.92 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811042735/vn2018sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811042735/vn2018Isup2.cdx

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811042735/vn2018Isup3.hkl

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

[Eu2(C7H5O2)6(C3H7NO)2(H2O)2]	F(000) = 1208
Mr = 1212.80	Dx = 1.653 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 5244 reflections
a = 11.6395 (2) Å	θ = 3.5–67.5°
b = 8.3692 (1) Å	µ = 18.84 mm−1
c = 25.5235 (4) Å	T = 291 K
β = 101.460 (2)°	Block, colourless
V = 2436.76 (6) Å3	0.36 × 0.32 × 0.32 mm
Z = 2

Oxford Gemini S Ultra diffractometer	4294 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray source	3860 reflections with I > 2σ(I)
mirror	Rint = 0.035
Detector resolution: 15.9149 pixels mm-1	θmax = 67.6°, θmin = 3.5°
ω scans	h = −13→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −9→5
Tmin = 0.056, Tmax = 0.065	l = −30→30
8782 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.120	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0781P)2] where P = (Fo2 + 2Fc2)/3
4294 reflections	(Δ/σ)max = 0.003
315 parameters	Δρmax = 1.20 e Å−3
3 restraints	Δρmin = −1.92 e Å−3

Experimental. CrysAlisPro (Oxford Diffraction, 2010). Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Eu1	0.58936 (2)	0.32204 (3)	0.555114 (10)	0.02985 (13)
O1	0.7648 (3)	0.4223 (4)	0.62602 (15)	0.0471 (8)
O5	0.5539 (3)	0.2337 (5)	0.64080 (14)	0.0455 (8)
O8	0.7148 (3)	0.0976 (5)	0.55948 (16)	0.0499 (9)
O2	0.6119 (3)	0.5789 (4)	0.59914 (14)	0.0426 (8)
O7	0.5164 (4)	0.2066 (5)	0.46868 (15)	0.0460 (8)
O4	0.4078 (3)	0.4576 (4)	0.53174 (15)	0.0450 (8)
O6	0.4632 (3)	0.0941 (4)	0.57245 (14)	0.0442 (8)
O3	0.7419 (3)	0.4010 (5)	0.50855 (15)	0.0530 (10)
C1	0.7736 (4)	0.6905 (6)	0.65945 (19)	0.0347 (11)
N1	0.8798 (4)	−0.0405 (6)	0.5577 (2)	0.0521 (11)
C8	0.7618 (4)	0.5287 (6)	0.42852 (19)	0.0379 (10)
C15	0.4233 (4)	0.0286 (6)	0.6587 (2)	0.0414 (11)
C14	0.6945 (4)	0.4870 (6)	0.47094 (19)	0.0366 (10)
C16	0.4494 (5)	0.0601 (8)	0.7132 (2)	0.0546 (14)
H16	0.5050	0.1374	0.7265	0.065*
C9	0.8819 (5)	0.5075 (8)	0.4393 (2)	0.0503 (14)
H9	0.9175	0.4610	0.4716	0.060*
C22	0.8222 (5)	0.0822 (7)	0.5720 (3)	0.0530 (13)
H22	0.8650	0.1618	0.5926	0.064*
C21	0.4839 (4)	0.1220 (6)	0.62194 (19)	0.0378 (10)
C20	0.3412 (5)	−0.0855 (8)	0.6391 (3)	0.0540 (14)
H20	0.3239	−0.1083	0.6027	0.065*
C6	0.8917 (6)	0.6821 (7)	0.6827 (3)	0.0544 (16)
H6	0.9329	0.5878	0.6808	0.065*
C7	0.7149 (4)	0.5550 (6)	0.62677 (18)	0.0366 (10)
C10	0.9505 (6)	0.5531 (9)	0.4038 (3)	0.0681 (19)
H10	1.0315	0.5405	0.4122	0.082*
C19	0.2840 (6)	−0.1669 (8)	0.6742 (4)	0.070 (2)
H19	0.2274	−0.2430	0.6611	0.084*
C18	0.3111 (6)	−0.1349 (10)	0.7283 (3)	0.070 (2)
H18	0.2733	−0.1902	0.7516	0.084*
C13	0.7090 (6)	0.5896 (8)	0.3796 (2)	0.0622 (17)
H13	0.6281	0.6020	0.3713	0.075*
C17	0.3936 (6)	−0.0219 (9)	0.7476 (3)	0.0668 (18)
H17	0.4120	−0.0005	0.7841	0.080*
C24	1.0054 (6)	−0.0566 (11)	0.5768 (4)	0.088 (3)
H24B	1.0207	−0.1451	0.6011	0.132*
H24A	1.0358	0.0396	0.5949	0.132*
H24C	1.0428	−0.0750	0.5470	0.132*
C5	0.9487 (7)	0.8130 (9)	0.7088 (3)	0.071 (2)
H5	1.0283	0.8074	0.7237	0.085*
C4	0.8876 (7)	0.9514 (9)	0.7128 (3)	0.077 (2)
H4	0.9261	1.0399	0.7300	0.093*
C12	0.7762 (8)	0.6330 (10)	0.3423 (3)	0.085 (3)
H12	0.7403	0.6717	0.3089	0.102*
C23	0.8170 (8)	−0.1668 (8)	0.5251 (4)	0.078 (2)
H23B	0.8175	−0.2616	0.5463	0.118*
H23A	0.8545	−0.1886	0.4956	0.118*
H23C	0.7376	−0.1339	0.5119	0.118*
C2	0.7126 (6)	0.8298 (7)	0.6634 (3)	0.0581 (16)
H2	0.6336	0.8371	0.6475	0.070*
C11	0.8975 (8)	0.6176 (10)	0.3556 (3)	0.082 (2)
H11	0.9431	0.6514	0.3317	0.098*
C3	0.7697 (7)	0.9596 (8)	0.6914 (3)	0.078 (2)
H3	0.7280	1.0519	0.6955	0.093*
H7B	0.527 (8)	0.112 (5)	0.458 (4)	0.117*
H7A	0.470 (7)	0.253 (10)	0.443 (3)	0.117*

	U11	U22	U33	U12	U13	U23
Eu1	0.03041 (19)	0.0315 (2)	0.02777 (18)	0.00101 (9)	0.00612 (12)	−0.00123 (9)
O1	0.0428 (19)	0.048 (2)	0.048 (2)	0.0050 (16)	0.0030 (15)	−0.0044 (17)
O5	0.050 (2)	0.047 (2)	0.0392 (18)	−0.0082 (17)	0.0086 (15)	−0.0080 (17)
O8	0.050 (2)	0.042 (2)	0.057 (2)	0.0100 (17)	0.0084 (17)	−0.0019 (18)
O2	0.0427 (18)	0.0357 (19)	0.0443 (18)	0.0032 (14)	−0.0039 (14)	−0.0070 (15)
O7	0.061 (2)	0.0381 (19)	0.0350 (18)	0.0043 (18)	−0.0003 (16)	−0.0049 (15)
O4	0.0327 (17)	0.053 (2)	0.051 (2)	0.0026 (15)	0.0118 (15)	−0.0110 (17)
O6	0.060 (2)	0.0393 (19)	0.0350 (18)	−0.0067 (16)	0.0138 (16)	0.0023 (15)
O3	0.0423 (19)	0.073 (3)	0.046 (2)	0.0038 (19)	0.0142 (16)	0.012 (2)
C1	0.037 (3)	0.040 (3)	0.025 (2)	0.0001 (19)	0.0017 (19)	−0.0030 (18)
N1	0.048 (2)	0.048 (3)	0.061 (3)	0.009 (2)	0.013 (2)	0.002 (2)
C8	0.037 (2)	0.045 (3)	0.035 (2)	0.004 (2)	0.0158 (19)	−0.004 (2)
C15	0.039 (3)	0.041 (3)	0.046 (3)	0.006 (2)	0.012 (2)	0.011 (2)
C14	0.029 (2)	0.044 (3)	0.038 (2)	−0.003 (2)	0.0085 (19)	−0.006 (2)
C16	0.064 (3)	0.062 (4)	0.040 (3)	0.000 (3)	0.015 (3)	0.006 (3)
C9	0.038 (3)	0.067 (4)	0.049 (3)	−0.004 (3)	0.016 (2)	−0.008 (3)
C22	0.055 (3)	0.044 (3)	0.058 (3)	−0.001 (3)	0.005 (3)	−0.001 (3)
C21	0.040 (3)	0.038 (3)	0.036 (2)	0.006 (2)	0.010 (2)	0.006 (2)
C20	0.052 (3)	0.058 (4)	0.054 (3)	−0.005 (3)	0.017 (3)	0.004 (3)
C6	0.049 (3)	0.058 (4)	0.049 (3)	0.005 (2)	−0.010 (3)	−0.010 (3)
C7	0.036 (2)	0.044 (3)	0.030 (2)	0.004 (2)	0.0063 (18)	−0.001 (2)
C10	0.059 (4)	0.078 (5)	0.078 (5)	−0.005 (3)	0.040 (4)	−0.005 (4)
C19	0.056 (4)	0.064 (4)	0.093 (6)	−0.011 (3)	0.022 (4)	0.019 (4)
C18	0.063 (4)	0.080 (5)	0.074 (5)	0.010 (4)	0.029 (4)	0.032 (4)
C13	0.069 (4)	0.076 (4)	0.046 (3)	0.036 (3)	0.022 (3)	0.012 (3)
C17	0.079 (4)	0.079 (5)	0.048 (3)	0.008 (4)	0.026 (3)	0.018 (3)
C24	0.061 (4)	0.100 (6)	0.101 (6)	0.029 (4)	0.011 (4)	0.014 (5)
C5	0.060 (4)	0.078 (5)	0.063 (4)	−0.008 (3)	−0.014 (3)	−0.008 (3)
C4	0.093 (5)	0.060 (4)	0.062 (4)	−0.017 (4)	−0.026 (4)	−0.009 (3)
C12	0.128 (7)	0.085 (5)	0.054 (4)	0.053 (5)	0.047 (4)	0.025 (4)
C23	0.083 (5)	0.060 (4)	0.095 (6)	0.006 (3)	0.024 (5)	−0.022 (4)
C2	0.054 (4)	0.059 (4)	0.053 (4)	0.008 (3)	−0.010 (3)	−0.013 (3)
C11	0.107 (6)	0.068 (5)	0.091 (6)	0.018 (4)	0.072 (5)	0.016 (4)
C3	0.099 (5)	0.051 (4)	0.066 (4)	0.012 (4)	−0.026 (4)	−0.027 (3)

Eu1—O8	2.368 (4)	C16—C17	1.374 (8)
Eu1—O4	2.368 (3)	C16—H16	0.9300
Eu1—O7	2.404 (4)	C9—C10	1.377 (8)
Eu1—O2	2.416 (3)	C9—H9	0.9300
Eu1—O3	2.416 (3)	C22—H22	0.9300
Eu1—O5	2.420 (4)	C20—C19	1.395 (9)
Eu1—O6	2.500 (3)	C20—H20	0.9300
Eu1—O1	2.584 (4)	C6—C5	1.380 (10)
Eu1—C21	2.837 (5)	C6—H6	0.9300
Eu1—C7	2.867 (5)	C10—C11	1.371 (11)
Eu1—O4i	2.889 (4)	C10—H10	0.9300
Eu1—C14	3.011 (5)	C19—C18	1.380 (12)
O1—C7	1.255 (6)	C19—H19	0.9300
O5—C21	1.271 (6)	C18—C17	1.368 (11)
O8—C22	1.235 (7)	C18—H18	0.9300
O2—C7	1.280 (6)	C13—C12	1.394 (9)
O7—H7B	0.86 (2)	C13—H13	0.9300
O7—H7A	0.86 (2)	C17—H17	0.9300
O4—C14i	1.267 (5)	C24—H24B	0.9600
O4—Eu1i	2.889 (4)	C24—H24A	0.9600
O6—C21	1.260 (6)	C24—H24C	0.9600
O3—C14	1.238 (6)	C5—C4	1.373 (10)
C1—C2	1.379 (8)	C5—H5	0.9300
C1—C6	1.388 (8)	C4—C3	1.374 (10)
C1—C7	1.490 (7)	C4—H4	0.9300
N1—C22	1.316 (7)	C12—C11	1.392 (12)
N1—C23	1.450 (9)	C12—H12	0.9300
N1—C24	1.453 (8)	C23—H23B	0.9600
C8—C13	1.376 (8)	C23—H23A	0.9600
C8—C9	1.382 (7)	C23—H23C	0.9600
C8—C14	1.498 (6)	C2—C3	1.393 (9)
C15—C20	1.373 (8)	C2—H2	0.9300
C15—C16	1.388 (8)	C11—H11	0.9300
C15—C21	1.501 (7)	C3—H3	0.9300
C14—O4i	1.267 (5)
O8—Eu1—O4	154.52 (13)	C13—C8—C9	118.7 (5)
O8—Eu1—O7	80.01 (13)	C13—C8—C14	122.6 (5)
O4—Eu1—O7	80.00 (13)	C9—C8—C14	118.6 (5)
O8—Eu1—O2	132.46 (13)	C20—C15—C16	119.7 (5)
O4—Eu1—O2	72.54 (12)	C20—C15—C21	120.9 (5)
O7—Eu1—O2	140.39 (13)	C16—C15—C21	119.4 (5)
O8—Eu1—O3	74.58 (14)	O3—C14—O4i	121.6 (4)
O4—Eu1—O3	116.81 (13)	O3—C14—C8	118.7 (4)
O7—Eu1—O3	79.55 (15)	O4i—C14—C8	119.8 (4)
O2—Eu1—O3	87.86 (14)	O3—C14—Eu1	50.3 (2)
O8—Eu1—O5	85.94 (14)	O4i—C14—Eu1	72.3 (3)
O4—Eu1—O5	94.03 (13)	C8—C14—Eu1	165.4 (3)
O7—Eu1—O5	127.89 (13)	C17—C16—C15	120.5 (6)
O2—Eu1—O5	82.75 (13)	C17—C16—H16	119.7
O3—Eu1—O5	143.29 (13)	C15—C16—H16	119.7
O8—Eu1—O6	76.39 (14)	C10—C9—C8	121.9 (6)
O4—Eu1—O6	83.33 (13)	C10—C9—H9	119.0
O7—Eu1—O6	75.10 (13)	C8—C9—H9	119.0
O2—Eu1—O6	127.60 (12)	O8—C22—N1	123.7 (6)
O3—Eu1—O6	144.16 (14)	O8—C22—H22	118.2
O5—Eu1—O6	52.81 (12)	N1—C22—H22	118.2
O8—Eu1—O1	80.26 (13)	O6—C21—O5	119.8 (4)
O4—Eu1—O1	124.21 (12)	O6—C21—C15	120.7 (5)
O7—Eu1—O1	149.22 (13)	O5—C21—C15	119.5 (4)
O2—Eu1—O1	52.24 (11)	O6—C21—Eu1	61.7 (3)
O3—Eu1—O1	72.56 (13)	O5—C21—Eu1	58.1 (2)
O5—Eu1—O1	73.68 (12)	C15—C21—Eu1	175.2 (4)
O6—Eu1—O1	122.27 (12)	C15—C20—C19	119.5 (6)
O8—Eu1—C21	80.78 (14)	C15—C20—H20	120.3
O4—Eu1—C21	87.89 (13)	C19—C20—H20	120.3
O7—Eu1—C21	101.45 (15)	C5—C6—C1	120.5 (6)
O2—Eu1—C21	105.40 (14)	C5—C6—H6	119.8
O3—Eu1—C21	154.81 (14)	C1—C6—H6	119.8
O5—Eu1—C21	26.48 (14)	O1—C7—O2	121.0 (5)
O6—Eu1—C21	26.34 (13)	O1—C7—C1	121.3 (4)
O1—Eu1—C21	98.42 (13)	O2—C7—C1	117.7 (4)
O8—Eu1—C7	106.16 (14)	O1—C7—Eu1	64.3 (3)
O4—Eu1—C7	98.69 (13)	O2—C7—Eu1	56.8 (2)
O7—Eu1—C7	154.32 (14)	C1—C7—Eu1	173.3 (3)
O2—Eu1—C7	26.30 (12)	C11—C10—C9	118.9 (7)
O3—Eu1—C7	78.27 (14)	C11—C10—H10	120.5
O5—Eu1—C7	77.76 (13)	C9—C10—H10	120.5
O6—Eu1—C7	130.46 (12)	C18—C19—C20	120.3 (7)
O1—Eu1—C7	25.97 (12)	C18—C19—H19	119.9
C21—Eu1—C7	104.14 (14)	C20—C19—H19	119.9
O8—Eu1—O4i	116.21 (12)	C17—C18—C19	119.9 (6)
O4—Eu1—O4i	69.30 (12)	C17—C18—H18	120.0
O7—Eu1—O4i	66.92 (12)	C19—C18—H18	120.0
O2—Eu1—O4i	76.82 (11)	C8—C13—C12	120.5 (6)
O3—Eu1—O4i	47.66 (11)	C8—C13—H13	119.8
O5—Eu1—O4i	156.69 (11)	C12—C13—H13	119.8
O6—Eu1—O4i	136.02 (11)	C18—C17—C16	120.1 (7)
O1—Eu1—O4i	101.67 (11)	C18—C17—H17	119.9
C21—Eu1—O4i	155.54 (12)	C16—C17—H17	119.9
C7—Eu1—O4i	88.47 (12)	N1—C24—H24B	109.5
O8—Eu1—C14	93.62 (13)	N1—C24—H24A	109.5
O4—Eu1—C14	93.99 (13)	H24B—C24—H24A	109.5
O7—Eu1—C14	69.44 (14)	N1—C24—H24C	109.5
O2—Eu1—C14	84.36 (13)	H24B—C24—H24C	109.5
O3—Eu1—C14	23.22 (13)	H24A—C24—H24C	109.5
O5—Eu1—C14	162.04 (12)	C4—C5—C6	119.9 (7)
O6—Eu1—C14	144.35 (12)	C4—C5—H5	120.1
O1—Eu1—C14	88.52 (12)	C6—C5—H5	120.1
C21—Eu1—C14	170.15 (14)	C5—C4—C3	120.2 (6)
C7—Eu1—C14	85.15 (13)	C5—C4—H4	119.9
O4i—Eu1—C14	24.70 (11)	C3—C4—H4	119.9
C7—O1—Eu1	89.7 (3)	C11—C12—C13	119.2 (7)
C21—O5—Eu1	95.4 (3)	C11—C12—H12	120.4
C22—O8—Eu1	132.7 (4)	C13—C12—H12	120.4
C7—O2—Eu1	96.9 (3)	N1—C23—H23B	109.5
Eu1—O7—H7B	128 (6)	N1—C23—H23A	109.5
Eu1—O7—H7A	126 (6)	H23B—C23—H23A	109.5
H7B—O7—H7A	106 (5)	N1—C23—H23C	109.5
C14i—O4—Eu1	166.2 (3)	H23B—C23—H23C	109.5
C14i—O4—Eu1i	83.0 (3)	H23A—C23—H23C	109.5
Eu1—O4—Eu1i	110.70 (12)	C1—C2—C3	119.8 (6)
C21—O6—Eu1	92.0 (3)	C1—C2—H2	120.1
C14—O3—Eu1	106.4 (3)	C3—C2—H2	120.1
C2—C1—C6	119.4 (5)	C10—C11—C12	120.7 (6)
C2—C1—C7	119.9 (5)	C10—C11—H11	119.7
C6—C1—C7	120.5 (5)	C12—C11—H11	119.7
C22—N1—C23	120.1 (5)	C4—C3—C2	120.1 (7)
C22—N1—C24	120.9 (6)	C4—C3—H3	119.9
C23—N1—C24	118.9 (6)	C2—C3—H3	119.9
O8—Eu1—O1—C7	175.9 (3)	O8—Eu1—C14—O4i	157.2 (3)
O4—Eu1—O1—C7	−11.9 (3)	O4—Eu1—C14—O4i	1.5 (3)
O7—Eu1—O1—C7	125.1 (3)	O7—Eu1—C14—O4i	79.3 (3)
O2—Eu1—O1—C7	−2.1 (3)	O2—Eu1—C14—O4i	−70.5 (3)
O3—Eu1—O1—C7	99.1 (3)	O3—Eu1—C14—O4i	−168.3 (5)
O5—Eu1—O1—C7	−95.5 (3)	O5—Eu1—C14—O4i	−114.8 (4)
O6—Eu1—O1—C7	−117.1 (3)	O6—Eu1—C14—O4i	85.6 (3)
C21—Eu1—O1—C7	−105.1 (3)	O1—Eu1—C14—O4i	−122.7 (3)
O4i—Eu1—O1—C7	60.9 (3)	C7—Eu1—C14—O4i	−96.9 (3)
C14—Eu1—O1—C7	81.9 (3)	O8—Eu1—C14—C8	10.2 (13)
O8—Eu1—O5—C21	−77.4 (3)	O4—Eu1—C14—C8	−145.4 (13)
O4—Eu1—O5—C21	77.0 (3)	O7—Eu1—C14—C8	−67.7 (13)
O7—Eu1—O5—C21	−3.4 (4)	O2—Eu1—C14—C8	142.6 (13)
O2—Eu1—O5—C21	148.8 (3)	O3—Eu1—C14—C8	44.8 (12)
O3—Eu1—O5—C21	−134.7 (3)	O5—Eu1—C14—C8	98.2 (13)
O6—Eu1—O5—C21	−1.4 (3)	O6—Eu1—C14—C8	−61.3 (13)
O1—Eu1—O5—C21	−158.4 (3)	O1—Eu1—C14—C8	90.4 (13)
C7—Eu1—O5—C21	175.1 (3)	C7—Eu1—C14—C8	116.2 (13)
O4i—Eu1—O5—C21	120.0 (3)	O4i—Eu1—C14—C8	−146.9 (14)
C14—Eu1—O5—C21	−166.6 (4)	C20—C15—C16—C17	0.0 (9)
O4—Eu1—O8—C22	169.1 (5)	C21—C15—C16—C17	178.9 (5)
O7—Eu1—O8—C22	130.3 (5)	C13—C8—C9—C10	3.4 (10)
O2—Eu1—O8—C22	−23.8 (6)	C14—C8—C9—C10	−175.5 (6)
O3—Eu1—O8—C22	48.5 (5)	Eu1—O8—C22—N1	−159.4 (4)
O5—Eu1—O8—C22	−100.1 (5)	C23—N1—C22—O8	0.5 (10)
O6—Eu1—O8—C22	−152.8 (5)	C24—N1—C22—O8	−175.8 (6)
O1—Eu1—O8—C22	−26.0 (5)	Eu1—O6—C21—O5	−2.5 (5)
C21—Eu1—O8—C22	−126.2 (5)	Eu1—O6—C21—C15	175.2 (4)
C7—Eu1—O8—C22	−24.1 (5)	Eu1—O5—C21—O6	2.6 (5)
O4i—Eu1—O8—C22	72.3 (5)	Eu1—O5—C21—C15	−175.1 (4)
C14—Eu1—O8—C22	61.9 (5)	C20—C15—C21—O6	−2.2 (8)
O8—Eu1—O2—C7	−0.7 (4)	C16—C15—C21—O6	179.0 (5)
O4—Eu1—O2—C7	173.6 (3)	C20—C15—C21—O5	175.5 (5)
O7—Eu1—O2—C7	−138.2 (3)	C16—C15—C21—O5	−3.3 (8)
O3—Eu1—O2—C7	−67.4 (3)	O8—Eu1—C21—O6	−77.9 (3)
O5—Eu1—O2—C7	77.0 (3)	O4—Eu1—C21—O6	79.2 (3)
O6—Eu1—O2—C7	106.9 (3)	O7—Eu1—C21—O6	−0.2 (3)
O1—Eu1—O2—C7	2.1 (3)	O2—Eu1—C21—O6	150.4 (3)
C21—Eu1—O2—C7	90.8 (3)	O3—Eu1—C21—O6	−89.9 (4)
O4i—Eu1—O2—C7	−114.3 (3)	O5—Eu1—C21—O6	−177.4 (5)
C14—Eu1—O2—C7	−90.5 (3)	O1—Eu1—C21—O6	−156.5 (3)
O8—Eu1—O4—C14i	78.9 (14)	C7—Eu1—C21—O6	177.6 (3)
O7—Eu1—O4—C14i	117.7 (14)	O4i—Eu1—C21—O6	58.5 (5)
O2—Eu1—O4—C14i	−91.2 (14)	O8—Eu1—C21—O5	99.5 (3)
O3—Eu1—O4—C14i	−169.5 (14)	O4—Eu1—C21—O5	−103.4 (3)
O5—Eu1—O4—C14i	−10.1 (14)	O7—Eu1—C21—O5	177.2 (3)
O6—Eu1—O4—C14i	41.7 (14)	O2—Eu1—C21—O5	−32.2 (3)
O1—Eu1—O4—C14i	−83.1 (14)	O3—Eu1—C21—O5	87.5 (5)
C21—Eu1—O4—C14i	15.6 (14)	O6—Eu1—C21—O5	177.4 (5)
C7—Eu1—O4—C14i	−88.3 (14)	O1—Eu1—C21—O5	20.9 (3)
O4i—Eu1—O4—C14i	−173.4 (15)	C7—Eu1—C21—O5	−5.0 (3)
C14—Eu1—O4—C14i	−174.0 (13)	O4i—Eu1—C21—O5	−124.1 (3)
O8—Eu1—O4—Eu1i	−107.7 (3)	C16—C15—C20—C19	0.7 (9)
O7—Eu1—O4—Eu1i	−68.97 (14)	C21—C15—C20—C19	−178.1 (5)
O2—Eu1—O4—Eu1i	82.15 (14)	C2—C1—C6—C5	−1.3 (11)
O3—Eu1—O4—Eu1i	3.84 (19)	C7—C1—C6—C5	174.0 (7)
O5—Eu1—O4—Eu1i	163.24 (13)	Eu1—O1—C7—O2	3.6 (5)
O6—Eu1—O4—Eu1i	−144.95 (14)	Eu1—O1—C7—C1	−175.9 (4)
O1—Eu1—O4—Eu1i	90.26 (16)	Eu1—O2—C7—O1	−3.9 (5)
C21—Eu1—O4—Eu1i	−170.98 (15)	Eu1—O2—C7—C1	175.7 (4)
C7—Eu1—O4—Eu1i	85.03 (14)	C2—C1—C7—O1	−173.9 (5)
O4i—Eu1—O4—Eu1i	0.0	C6—C1—C7—O1	10.8 (8)
C14—Eu1—O4—Eu1i	−0.67 (15)	C2—C1—C7—O2	6.5 (7)
O8—Eu1—O6—C21	96.7 (3)	C6—C1—C7—O2	−168.7 (5)
O4—Eu1—O6—C21	−98.8 (3)	O8—Eu1—C7—O1	−4.2 (3)
O7—Eu1—O6—C21	179.8 (3)	O4—Eu1—C7—O1	170.1 (3)
O2—Eu1—O6—C21	−36.9 (3)	O7—Eu1—C7—O1	−104.9 (4)
O3—Eu1—O6—C21	133.4 (3)	O2—Eu1—C7—O1	176.3 (5)
O5—Eu1—O6—C21	1.5 (3)	O3—Eu1—C7—O1	−74.2 (3)
O1—Eu1—O6—C21	27.8 (3)	O5—Eu1—C7—O1	77.8 (3)
C7—Eu1—O6—C21	−3.0 (4)	O6—Eu1—C7—O1	81.5 (3)
O4i—Eu1—O6—C21	−149.5 (3)	C21—Eu1—C7—O1	80.1 (3)
C14—Eu1—O6—C21	173.7 (3)	O4i—Eu1—C7—O1	−121.1 (3)
O8—Eu1—O3—C14	144.0 (4)	C14—Eu1—C7—O1	−96.6 (3)
O4—Eu1—O3—C14	−11.5 (4)	O8—Eu1—C7—O2	179.5 (3)
O7—Eu1—O3—C14	61.6 (4)	O4—Eu1—C7—O2	−6.2 (3)
O2—Eu1—O3—C14	−80.7 (4)	O7—Eu1—C7—O2	78.8 (4)
O5—Eu1—O3—C14	−155.5 (3)	O3—Eu1—C7—O2	109.5 (3)
O6—Eu1—O3—C14	107.0 (4)	O5—Eu1—C7—O2	−98.5 (3)
O1—Eu1—O3—C14	−131.6 (4)	O6—Eu1—C7—O2	−94.8 (3)
C21—Eu1—O3—C14	156.3 (3)	O1—Eu1—C7—O2	−176.3 (5)
C7—Eu1—O3—C14	−105.4 (4)	C21—Eu1—C7—O2	−96.2 (3)
O4i—Eu1—O3—C14	−6.6 (3)	O4i—Eu1—C7—O2	62.6 (3)
Eu1—O3—C14—O4i	13.2 (6)	C14—Eu1—C7—O2	87.1 (3)
Eu1—O3—C14—C8	−168.3 (4)	C8—C9—C10—C11	−1.8 (11)
C13—C8—C14—O3	164.0 (6)	C15—C20—C19—C18	−1.1 (10)
C9—C8—C14—O3	−17.0 (8)	C20—C19—C18—C17	0.6 (11)
C13—C8—C14—O4i	−17.4 (8)	C9—C8—C13—C12	−1.7 (10)
C9—C8—C14—O4i	161.5 (5)	C14—C8—C13—C12	177.2 (6)
C13—C8—C14—Eu1	125.8 (12)	C19—C18—C17—C16	0.2 (11)
C9—C8—C14—Eu1	−55.2 (15)	C15—C16—C17—C18	−0.5 (10)
O8—Eu1—C14—O3	−34.6 (4)	C1—C6—C5—C4	1.4 (13)
O4—Eu1—C14—O3	169.7 (4)	C6—C5—C4—C3	0.7 (14)
O7—Eu1—C14—O3	−112.5 (4)	C8—C13—C12—C11	−1.6 (12)
O2—Eu1—C14—O3	97.8 (4)	C6—C1—C2—C3	−0.9 (10)
O5—Eu1—C14—O3	53.4 (6)	C7—C1—C2—C3	−176.2 (6)
O6—Eu1—C14—O3	−106.1 (4)	C9—C10—C11—C12	−1.6 (12)
O1—Eu1—C14—O3	45.6 (4)	C13—C12—C11—C10	3.3 (13)
C7—Eu1—C14—O3	71.3 (4)	C5—C4—C3—C2	−2.9 (13)
O4i—Eu1—C14—O3	168.3 (5)	C1—C2—C3—C4	3.0 (12)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7B···O6ii	0.86 (2)	1.90 (2)	2.756 (5)	174 (9)
O7—H7A···O2i	0.86 (2)	1.90 (4)	2.724 (5)	159 (9)

Table 1

Selected bond lengths (Å)

Eu1—O8	2.368 (4)
Eu1—O4	2.368 (3)
Eu1—O7	2.404 (4)
Eu1—O2	2.416 (3)
Eu1—O3	2.416 (3)
Eu1—O5	2.420 (4)
Eu1—O6	2.500 (3)
Eu1—O1	2.584 (4)
Eu1—O4i	2.889 (4)

Symmetry code: (i) .

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H7B⋯O6ii	0.86 (2)	1.90 (2)	2.756 (5)	174 (9)
O7—H7A⋯O2i	0.86 (2)	1.90 (4)	2.724 (5)	159 (9)

Symmetry codes: (i) ; (ii) .