(4,4′-Bipyridyl-κN)tetra­kis(nitrato-κ²N,N′)[4-(4-pyridyl)pyridinium-κN¹]europium(III)

In the title complex, [Eu(NO₃)₄(C₁₀H₉N₂)(C₁₀H₈N₂)], each Eu^III ion is ten-coordinated by an N atom from a 4,4′-bipyridine mol­ecule, an N atom from a 4′-(4-pyridyl)­pyridinium cation and eight O atoms from four different nitrate ions. A C₂ axis passes through the Eu^III ion. Adjacent mol­ecules are connected by strong and weak hydrogen bonds to construct a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.018
• wR factor = 0.049
• Data-to-parameter ratio = 11.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Eu1    -   O6      ..      11.98 su

Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.97
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.94
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Eu1    -   O1      ..       9.98 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Eu1    -   O3      ..       9.71 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Eu1    -   O4      ..       7.70 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         O1
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Eu1

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.943
            Tmax scaled      0.583 Tmin scaled      0.503
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT794_ALERT_5_G Check Predicted Bond Valency for Eu1         (3)       2.49
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          1

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   5 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   6 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

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S1. Comment

Rare earth complexes with luminescent properties feature long emission life but narrow emission bands. Complexes of different rare earth metals yield each of the three basic colors (Eu³⁺ for red, Tb³⁺ for green and Eu²⁺ for blue) and represent potential candidates for the preparation of new generational display and other luminescent instruments (Shaheen et al., 1999; Adachi et al.,2000). Past research shows it is important to select ligands which can match the central metal ions in energy and thus lead to 'antenna effect' (Sabbatini et al.,1993). Complexes of Eu^III ion with 4,4'-bipyridine or its dioxide derivative as a bidentate ligand have been reported (Cotton et al.,2003), but to our knowledge, complexes of Eu^III with 4,4'-bipyridyl as monodentate ligand have not been reported. In this paper we report the crystal structure of the title complex. As shown in Fig. 1, in this complex every Eu^III ion is ten coordinate defined by two N atoms from two different monodentate 4,4'-bipyridine molecules and eight O atoms from four different bidentate nitrate anions. The Eu—N bond length is 2.626 (2) Å. The Eu—O bond lengths range from 2.4620 (17) to 2.5160 (17) Å. The C₂ symmetry element existing in the crystal structure goes through the Eu^IIIions. One hydrogen ion is distributed between the two non-coordinated N atoms of the 4,4'-bipyridine ligands in 50% occupation ratio and takes part in forming an N—H···N strong intermolecular hydrogen bond to give a zigzag array. As depicted in Fig. 2, the zigzag strings are found to extend by forming strong hydrogen bonds described above along the a axis, in the packing structure of the crystal. Weak hydrogen bonds between nitrate O atoms and H atoms of pyridine rings connect different strings in adjacent molecules to form a three-dimensional network.

Related literature

For related literature, see: Adachi et al. (2000); Cotton et al. (2003); Sabbatini et al. (1993); Shaheen et al. (1999).

S2. Experimental

A mixture of 4,4'-bipyridine (0.25 g) and Eu(NO₃)₃ (0.28 g) in the molar ratio of 2:1 was added to methanol (20 ml). The mixture was heated at 350 K for 5 h under reflux with stirring. The resulting solution was then filtered. Single crystals suitable for X-ray diffraction analysis formed after a week by slow evaporation of the solvent.

S3. Refinement

The H atoms were positioned geometrically and treated as riding on their parent atoms, with C—H = 0.93 Å (pyridine ring) and 0.96 Å(methyl), and N—H = 0.86 Å (amine group), and with U_iso(H) = 1.2U_eq(C). H11 and H11A were defined as first and second disordered parts in a 50% occupation ratio and fully refined.

Computing details

Data collection: SMART (Bruker, 2000); cell refinement: SMART; data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXL97; software used to prepare material for publication: SHELXL97.

Figures

	Fig. 1. The asymmetric unit of (I), showing 35% probability displacement ellipsoids.
	Fig. 2. The one dimensional zigzag string of the title complex extending along the a axis.

(4,4'-Bipyridyl-κN)[4'-(4-pyridyl)pyridinium-κN^1']tetrakis(nitrato- κ²N,N')europium(III)

Crystal data

[Eu(NO3)4(C10H9N2)(C10H8N2)]	Z = 4
Mr = 713.38	F(000) = 1408
Monoclinic, C2/c	Dx = 1.879 Mg m^−3
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 20.136 (5) Å	θ = 2.1–28.4°
b = 7.8079 (14) Å	µ = 2.57 mm^−1
c = 18.310 (3) Å	T = 293 K
β = 118.834 (2)°	Block, yellow
V = 2521.8 (9) Å^3	0.28 × 0.26 × 0.21 mm

Data collection

Bruker APEXII area-detector diffractometer	2211 independent reflections
Radiation source: fine-focus sealed tube	2153 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 25.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −23→24
Tmin = 0.533, Tmax = 0.619	k = −9→9
7437 measured reflections	l = −21→21

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.018	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.031P)^2 + 0.9897P] where P = (Fo^2 + 2Fc^2)/3
2211 reflections	(Δ/σ)max < 0.001
191 parameters	Δρmax = 0.50 e Å^−3
1 restraint	Δρmin = −0.56 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.

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 (Ų)

	x	y	z	Uiso*/Ueq	Occ. (<1)
H11	0.243 (7)	1.222 (16)	0.018 (7)	0.13 (5)*	0.50 (10)
Eu1	0.0000	0.338536 (17)	0.2500	0.03085 (8)
O4	0.00208 (11)	0.3047 (3)	0.11446 (11)	0.0480 (4)
O3	0.12196 (11)	0.2141 (3)	0.27142 (11)	0.0468 (4)
O6	−0.09200 (10)	0.4418 (2)	0.11018 (11)	0.0478 (4)
N2	−0.05805 (13)	0.3852 (3)	0.07139 (12)	0.0427 (5)
N1	0.12672 (12)	0.0900 (3)	0.31810 (12)	0.0407 (5)
O1	0.07166 (11)	0.0719 (3)	0.33171 (13)	0.0554 (5)
O2	0.18155 (12)	−0.0037 (3)	0.34727 (12)	0.0622 (5)
O5	−0.08280 (14)	0.4120 (3)	−0.00236 (11)	0.0702 (6)
N3	0.06444 (12)	0.6021 (3)	0.22022 (12)	0.0399 (4)
C3	0.12606 (15)	0.8304 (3)	0.15042 (14)	0.0340 (5)
C4	0.05361 (16)	0.8533 (3)	0.13925 (16)	0.0396 (6)
H4	0.0244	0.9459	0.1087	0.048*
C2	0.16818 (15)	0.6951 (3)	0.19990 (15)	0.0412 (5)
H2	0.2178	0.6777	0.2108	0.049*
C5	0.02512 (15)	0.7364 (3)	0.17410 (15)	0.0411 (5)
H5	−0.0241	0.7521	0.1649	0.049*
C1	0.13539 (14)	0.5861 (4)	0.23286 (15)	0.0437 (6)
H1	0.1645	0.4959	0.2660	0.052*
C6	0.15731 (13)	0.9448 (3)	0.10950 (13)	0.0347 (5)
C7	0.20534 (15)	0.8784 (4)	0.08172 (15)	0.0399 (5)
H7	0.2178	0.7627	0.0882	0.048*
C10	0.13999 (17)	1.1166 (4)	0.09719 (19)	0.0509 (7)
H10	0.1071	1.1645	0.1138	0.061*
N4	0.21769 (15)	1.1517 (3)	0.03422 (15)	0.0461 (6)
C8	0.23413 (14)	0.9869 (4)	0.04437 (15)	0.0444 (6)
H8	0.2661	0.9424	0.0257	0.053*
C9	0.17182 (18)	1.2178 (4)	0.05995 (19)	0.0571 (7)
H9	0.1608	1.3343	0.0529	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Eu1	0.03323 (11)	0.02896 (11)	0.04004 (11)	0.000	0.02536 (8)	0.000
O4	0.0522 (12)	0.0524 (11)	0.0503 (9)	0.0116 (9)	0.0333 (9)	0.0021 (8)
O3	0.0481 (10)	0.0443 (10)	0.0590 (10)	0.0099 (9)	0.0345 (8)	0.0132 (9)
O6	0.0424 (10)	0.0494 (11)	0.0557 (9)	0.0070 (8)	0.0268 (8)	−0.0007 (8)
N2	0.0485 (13)	0.0384 (11)	0.0410 (10)	−0.0004 (10)	0.0214 (10)	−0.0026 (9)
N1	0.0442 (12)	0.0352 (12)	0.0429 (10)	0.0027 (9)	0.0210 (9)	−0.0010 (9)
O1	0.0572 (12)	0.0441 (11)	0.0790 (12)	0.0028 (9)	0.0442 (10)	0.0143 (10)
O2	0.0588 (12)	0.0558 (13)	0.0664 (11)	0.0266 (10)	0.0258 (9)	0.0138 (10)
O5	0.0959 (17)	0.0657 (15)	0.0396 (10)	0.0070 (13)	0.0253 (10)	0.0010 (10)
N3	0.0473 (13)	0.0380 (11)	0.0475 (10)	−0.0024 (9)	0.0332 (9)	0.0034 (9)
C3	0.0401 (13)	0.0324 (13)	0.0387 (11)	−0.0038 (8)	0.0262 (10)	−0.0016 (8)
C4	0.0447 (15)	0.0358 (13)	0.0524 (13)	0.0048 (9)	0.0346 (12)	0.0064 (10)
C2	0.0358 (13)	0.0450 (14)	0.0475 (12)	0.0003 (10)	0.0238 (11)	0.0091 (11)
C5	0.0466 (14)	0.0350 (13)	0.0578 (13)	0.0022 (11)	0.0382 (12)	0.0027 (11)
C1	0.0404 (14)	0.0450 (16)	0.0480 (12)	0.0022 (11)	0.0230 (11)	0.0140 (11)
C6	0.0349 (11)	0.0372 (12)	0.0390 (10)	−0.0024 (9)	0.0234 (9)	0.0022 (9)
C7	0.0405 (13)	0.0396 (12)	0.0486 (12)	0.0024 (10)	0.0286 (11)	0.0041 (10)
C10	0.0651 (19)	0.0383 (13)	0.0764 (18)	0.0059 (13)	0.0558 (16)	0.0090 (13)
N4	0.0494 (14)	0.0488 (15)	0.0536 (12)	−0.0056 (9)	0.0356 (11)	0.0093 (9)
C8	0.0412 (13)	0.0527 (16)	0.0513 (12)	−0.0010 (11)	0.0318 (11)	0.0043 (11)
C9	0.073 (2)	0.0411 (15)	0.0819 (18)	0.0055 (14)	0.0567 (17)	0.0146 (15)

Geometric parameters (Å, º)

Eu1—O6^i	2.4620 (18)	C3—C4	1.383 (4)
Eu1—O6	2.4620 (18)	C3—C2	1.384 (3)
Eu1—O3	2.4900 (19)	C3—C6	1.487 (3)
Eu1—O3^i	2.4900 (19)	C4—C5	1.386 (3)
Eu1—O4^i	2.5159 (18)	C4—H4	0.9300
Eu1—O4	2.5160 (18)	C2—C1	1.381 (4)
Eu1—O1^i	2.563 (2)	C2—H2	0.9300
Eu1—O1	2.563 (2)	C5—H5	0.9300
Eu1—N3	2.626 (2)	C1—H1	0.9300
Eu1—N3^i	2.626 (2)	C6—C10	1.377 (4)
Eu1—N2^i	2.917 (2)	C6—C7	1.392 (3)
Eu1—N1^i	2.960 (2)	C7—C8	1.380 (4)
O4—N2	1.250 (3)	C7—H7	0.9300
O3—N1	1.265 (3)	C10—C9	1.386 (4)
O6—N2	1.279 (3)	C10—H10	0.9300
N2—O5	1.211 (3)	N4—C8	1.319 (4)
N1—O2	1.213 (3)	N4—C9	1.327 (4)
N1—O1	1.256 (3)	N4—H11	0.89 (2)
N3—C1	1.338 (3)	C8—H8	0.9300
N3—C5	1.340 (4)	C9—H9	0.9300
O6^i—Eu1—O6	141.76 (9)	O6—Eu1—N1^i	73.34 (6)
O6^i—Eu1—O3	76.92 (6)	O3—Eu1—N1^i	113.25 (7)
O6—Eu1—O3	118.81 (6)	O3^i—Eu1—N1^i	24.97 (6)
O6^i—Eu1—O3^i	118.81 (6)	O4^i—Eu1—N1^i	85.74 (6)
O6—Eu1—O3^i	76.92 (6)	O4—Eu1—N1^i	86.37 (6)
O3—Eu1—O3^i	134.06 (10)	O1^i—Eu1—N1^i	24.99 (6)
O6^i—Eu1—O4^i	51.01 (6)	O1—Eu1—N1^i	80.89 (6)
O6—Eu1—O4^i	134.26 (7)	N3—Eu1—N1^i	146.93 (6)
O3—Eu1—O4^i	106.74 (6)	N3^i—Eu1—N1^i	100.91 (7)
O3^i—Eu1—O4^i	68.29 (6)	N2^i—Eu1—N1^i	110.62 (6)
O6^i—Eu1—O4	134.26 (7)	N2—O4—Eu1	95.61 (13)
O6—Eu1—O4	51.01 (6)	N1—O3—Eu1	98.80 (14)
O3—Eu1—O4	68.29 (6)	N2—O6—Eu1	97.39 (14)
O3^i—Eu1—O4	106.74 (6)	O5—N2—O4	122.9 (2)
O4^i—Eu1—O4	167.96 (9)	O5—N2—O6	121.1 (2)
O6^i—Eu1—O1^i	143.35 (6)	O4—N2—O6	115.97 (19)
O6—Eu1—O1^i	74.31 (7)	O2—N1—O1	123.2 (2)
O3—Eu1—O1^i	90.56 (6)	O2—N1—O3	121.1 (2)
O3^i—Eu1—O1^i	49.94 (6)	O1—N1—O3	115.7 (2)
O4^i—Eu1—O1^i	102.59 (6)	N1—O1—Eu1	95.47 (13)
O4—Eu1—O1^i	67.15 (7)	C1—N3—C5	116.0 (2)
O6^i—Eu1—O1	74.31 (7)	C1—N3—Eu1	118.97 (17)
O6—Eu1—O1	143.35 (6)	C5—N3—Eu1	122.90 (16)
O3—Eu1—O1	49.94 (6)	C4—C3—C2	117.7 (2)
O3^i—Eu1—O1	90.56 (6)	C4—C3—C6	121.4 (2)
O4^i—Eu1—O1	67.14 (7)	C2—C3—C6	120.9 (2)
O4—Eu1—O1	102.60 (6)	C3—C4—C5	119.2 (2)
O1^i—Eu1—O1	71.41 (10)	C3—C4—H4	120.4
O6^i—Eu1—N3	76.11 (6)	C5—C4—H4	120.4
O6—Eu1—N3	74.15 (7)	C1—C2—C3	119.0 (2)
O3—Eu1—N3	77.88 (7)	C1—C2—H2	120.5
O3^i—Eu1—N3	145.24 (7)	C3—C2—H2	120.5
O4^i—Eu1—N3	122.13 (6)	N3—C5—C4	123.7 (2)
O4—Eu1—N3	68.44 (7)	N3—C5—H5	118.1
O1^i—Eu1—N3	135.27 (6)	C4—C5—H5	118.1
O1—Eu1—N3	124.20 (7)	N3—C1—C2	124.2 (2)
O6^i—Eu1—N3^i	74.15 (7)	N3—C1—H1	117.9
O6—Eu1—N3^i	76.11 (6)	C2—C1—H1	117.9
O3—Eu1—N3^i	145.24 (7)	C10—C6—C7	117.9 (2)
O3^i—Eu1—N3^i	77.88 (7)	C10—C6—C3	122.2 (2)
O4^i—Eu1—N3^i	68.44 (7)	C7—C6—C3	119.9 (2)
O4—Eu1—N3^i	122.13 (6)	C8—C7—C6	119.0 (3)
O1^i—Eu1—N3^i	124.20 (6)	C8—C7—H7	120.5
O1—Eu1—N3^i	135.27 (6)	C6—C7—H7	120.5
N3—Eu1—N3^i	76.83 (9)	C6—C10—C9	119.7 (3)
O6^i—Eu1—N2^i	25.77 (6)	C6—C10—H10	120.2
O6—Eu1—N2^i	144.95 (6)	C9—C10—H10	120.2
O3—Eu1—N2^i	92.34 (6)	C8—N4—C9	120.0 (2)
O3^i—Eu1—N2^i	93.26 (6)	C8—N4—H11	120 (10)
O4^i—Eu1—N2^i	25.24 (6)	C9—N4—H11	119 (10)
O4—Eu1—N2^i	158.55 (7)	N4—C8—C7	122.1 (2)
O1^i—Eu1—N2^i	124.35 (7)	N4—C8—H8	118.9
O1—Eu1—N2^i	68.82 (7)	C7—C8—H8	118.9
N3—Eu1—N2^i	99.43 (6)	N4—C9—C10	121.3 (3)
N3^i—Eu1—N2^i	68.91 (6)	N4—C9—H9	119.4
O6^i—Eu1—N1^i	135.74 (6)	C10—C9—H9	119.4
O6^i—Eu1—O4—N2	−127.84 (16)	N3—Eu1—O1—N1	−23.62 (17)
O6—Eu1—O4—N2	0.63 (14)	N3^i—Eu1—O1—N1	−130.75 (14)
O3—Eu1—O4—N2	−171.12 (17)	N2^i—Eu1—O1—N1	−110.70 (15)
O3^i—Eu1—O4—N2	57.44 (17)	N1^i—Eu1—O1—N1	132.90 (14)
O4^i—Eu1—O4—N2	121.24 (16)	O6^i—Eu1—N3—C1	73.72 (18)
O1^i—Eu1—O4—N2	88.55 (16)	O6—Eu1—N3—C1	−130.59 (19)
O1—Eu1—O4—N2	151.89 (15)	O3—Eu1—N3—C1	−5.60 (17)
N3—Eu1—O4—N2	−86.04 (16)	O3^i—Eu1—N3—C1	−165.32 (15)
N3^i—Eu1—O4—N2	−28.55 (19)	O4^i—Eu1—N3—C1	96.69 (18)
N2^i—Eu1—O4—N2	−144.4 (2)	O4—Eu1—N3—C1	−76.82 (18)
N1^i—Eu1—O4—N2	72.07 (16)	O1^i—Eu1—N3—C1	−83.9 (2)
O6^i—Eu1—O3—N1	78.56 (15)	O1—Eu1—N3—C1	14.0 (2)
O6—Eu1—O3—N1	−139.02 (14)	N3^i—Eu1—N3—C1	150.4 (2)
O3^i—Eu1—O3—N1	−39.07 (13)	N2^i—Eu1—N3—C1	84.77 (18)
O4^i—Eu1—O3—N1	36.66 (16)	N1^i—Eu1—N3—C1	−119.82 (18)
O4—Eu1—O3—N1	−131.72 (16)	O6^i—Eu1—N3—C5	−123.43 (19)
O1^i—Eu1—O3—N1	−66.67 (15)	O6—Eu1—N3—C5	32.26 (18)
O1—Eu1—O3—N1	−1.81 (13)	O3—Eu1—N3—C5	157.24 (19)
N3—Eu1—O3—N1	156.89 (16)	O3^i—Eu1—N3—C5	−2.5 (2)
N3^i—Eu1—O3—N1	112.80 (16)	O4^i—Eu1—N3—C5	−100.46 (19)
N2^i—Eu1—O3—N1	57.74 (15)	O4—Eu1—N3—C5	86.02 (18)
N1^i—Eu1—O3—N1	−55.91 (18)	O1^i—Eu1—N3—C5	78.9 (2)
O6^i—Eu1—O6—N2	114.43 (15)	O1—Eu1—N3—C5	176.88 (17)
O3—Eu1—O6—N2	8.13 (17)	N3^i—Eu1—N3—C5	−46.80 (16)
O3^i—Eu1—O6—N2	−125.26 (15)	N2^i—Eu1—N3—C5	−112.38 (18)
O4^i—Eu1—O6—N2	−166.10 (13)	N1^i—Eu1—N3—C5	43.0 (2)
O4—Eu1—O6—N2	−0.62 (14)	C2—C3—C4—C5	−3.2 (4)
O1^i—Eu1—O6—N2	−73.66 (15)	C6—C3—C4—C5	175.7 (2)
O1—Eu1—O6—N2	−52.45 (19)	C4—C3—C2—C1	2.5 (4)
N3—Eu1—O6—N2	74.22 (15)	C6—C3—C2—C1	−176.3 (2)
N3^i—Eu1—O6—N2	154.21 (16)	C1—N3—C5—C4	1.0 (4)
N2^i—Eu1—O6—N2	158.00 (15)	Eu1—N3—C5—C4	−162.3 (2)
N1^i—Eu1—O6—N2	−99.67 (15)	C3—C4—C5—N3	1.4 (4)
Eu1—O4—N2—O5	177.7 (2)	C5—N3—C1—C2	−1.8 (4)
Eu1—O4—N2—O6	−1.0 (2)	Eu1—N3—C1—C2	162.2 (2)
Eu1—O6—N2—O5	−177.7 (2)	C3—C2—C1—N3	0.0 (4)
Eu1—O6—N2—O4	1.1 (2)	C4—C3—C6—C10	34.9 (4)
Eu1—O3—N1—O2	−176.7 (2)	C2—C3—C6—C10	−146.3 (3)
Eu1—O3—N1—O1	3.1 (2)	C4—C3—C6—C7	−144.6 (2)
O2—N1—O1—Eu1	176.8 (2)	C2—C3—C6—C7	34.2 (3)
O3—N1—O1—Eu1	−3.0 (2)	C10—C6—C7—C8	0.8 (4)
O6^i—Eu1—O1—N1	−84.12 (15)	C3—C6—C7—C8	−179.6 (2)
O6—Eu1—O1—N1	87.49 (17)	C7—C6—C10—C9	−1.6 (4)
O3—Eu1—O1—N1	1.81 (13)	C3—C6—C10—C9	178.9 (3)
O3^i—Eu1—O1—N1	156.02 (14)	C9—N4—C8—C7	−0.3 (4)
O4^i—Eu1—O1—N1	−137.91 (16)	C6—C7—C8—N4	0.1 (4)
O4—Eu1—O1—N1	48.72 (15)	C8—N4—C9—C10	−0.4 (5)
O1^i—Eu1—O1—N1	109.05 (16)	C6—C10—C9—N4	1.4 (5)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H11···N4^ii	0.89 (6)	1.80 (6)	2.682 (4)	169 (6)

Symmetry code: (ii) −x+1/2, −y+5/2, −z.