Tris[2-(2-pyridylimino­meth­yl)phenol­ato(0.67−)]europium(III) nitrate

Zhao, Q.-H.; Chen, H.-Y.; Li, L.-N.; Xie, M.-J.

doi:10.1107/S1600536809017206

Tris[2-(2-pyridyliminomethyl)phenolato(0.67−)]europium(III) nitrate

Q.-H. Zhao, H.-Y. Chen, L.-N. Li and M.-J. Xie

The title compound, [Eu(C₁₂H_9.33N₂O)₃]NO₃, was obtained by the reaction of Eu(NO₃)·3H₂O and the Schiff base ligand 2-(2-pyridyliminomethyl)phenol. The Eu atom is located on a threefold rotation axis and is nine-coordinated by three tridentate Schiff base ligands in a distorted tricapped trigonal-prismatic geometry. The O atom at the phenol hydroxy group is partially deprotonated and the H atoms are modelled with one-third occupancy according to the space group R $\overline{3}$ . Offset face-to-face π–π [centroid–centroid distance = 3.886 (3) Å] and edge-to-face C—H

π interactions are found between adjacent molecules. An intramolecular O—H

N hydrogen bond is also present.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536809017206/bq2130sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536809017206/bq2130Isup2.hkl Contains datablock I

CCDC reference: 738111

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.010 Å
R factor = 0.054
wR factor = 0.128
Data-to-parameter ratio = 16.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT342_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...         10
PLAT068_ALERT_1_C Reported F000 Differs from Calcd (or Missing)...          ?
PLAT194_ALERT_1_C Missing _cell_measurement_reflns_used datum ....          ?
PLAT731_ALERT_1_C Bond    Calc     1.17(4), Rep   1.167(16) ......       2.50 su-Ra
              O2   -N3      1.555   1.555
PLAT731_ALERT_1_C Bond    Calc     1.17(4), Rep   1.167(16) ......       2.50 su-Ra
              N3   -O2      1.555   2.645
PLAT731_ALERT_1_C Bond    Calc     1.17(5), Rep   1.167(16) ......       3.12 su-Ra
              N3   -O2      1.555   3.765

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:C36 H28 Eu1 N7 O6
            Atom count from the _atom_site data:  C36 H27.99 Eu1 N7 O6
CELLZ01_ALERT_1_G Difference between formula and atom_site contents detected.
CELLZ01_ALERT_1_G ALERT: check formula stoichiometry or atom site occupancies.
           From the CIF: _cell_formula_units_Z    6
           From the CIF: _chemical_formula_sum  C36 H28 Eu N7 O6
           TEST: Compare cell contents of formula and atom_site data

           atom    Z*formula  cif sites diff
           C        216.00    216.00    0.00
           H        168.00    167.94    0.06
           Eu         6.00      6.00    0.00
           N         42.00     42.00    0.00
           O         36.00     36.00    0.00
PLAT066_ALERT_1_G Predicted and Reported Transmissions Identical .          ?
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
PLAT764_ALERT_4_G Overcomplete CIF Bond List Detected (Rep/Expd) .       1.19 Ratio
PLAT779_ALERT_4_G Suspect or Irrelevant (Bond) Angle in CIF ......      36.00 Deg.
              O1   -C8   -H1B     1.555   1.555   1.555

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

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

Comment top

During the last decades, considerable amount of work was devoted to the synthesis, structure and properties of transition metal complexes derived from Schiff bases because of their potential applications in catalysis and enzymatic reactions, magnetism and molecular architecture (Henry et al. 2008; Li & Zhang, 2004). Herein, we report the Schiff base complex mentioned in the title by solvent evaporation method (Sreenivasulu et al., 2005).

As shown in Fig. 1, the central Eu of the title compound is nine-coordinated. The coordination environment is defined by six N atoms and three O atoms from the three different N-Salicylidene-2-aminopyride ligands. (You et al., 2004). The bond length of Eu(1)—N(1) (2.681 (5) Å) and Eu(1)—N(2) (2.540 (5) Å) are longer than Eu(1)—O(1) (2.332 (4) Å). The bond angle of O(1)#1-Eu(1)—N(2)#2 (69.37 (14)°) is larger than N(2)#2-Eu(1)—N(1) (51.11 (15)°).

In one schiff base ligand, all of the atoms are almost in one plane. The most evident distortion is associated with the C12 atom, which is 0.2017 (3)Å away from the mean plane. Meanwhile, the two aromatic rings of the same ligand form a dihedral angle of 14.072 (4)°, and between every two neighbour ligands coordinated to the Eu, the schiff bases appear an angle of 80.768 (3), 80.292 (4), 80.933 (3)°, respectively. The phenyl ring and pyridine ring of adjacent molecules exist the offset face-to-face pi-pi stacking interactions, with a distance of 3.886 (3)Å (13.245 (4)°) and the edge-to-face C—H-pi interactions were founded between the two phenyl rings of adjacent molecules with the distance of 3.785 (5) Å. The intramolecular hydrogen-bonding was also found between O1 and N2 atoms with the N···O separation of 2.783 (6) Å.

Related literature top

For the potential applications of transition metal complexes derived from Schiff bases, see: Li & Zhang (2004); Henry et al. (2008). For the synthesis, see: Sreenivasulu et al. (2005). For a related structure, see: You et al. (2004). Cg1 is the centroid of the C7–C12 benzene ring.

Experimental top

All chemicals used (reagent grade) were commercially available. Salicylaldehyde (0.122 g, 1 mmol) and 2-aminomethylpyridine (0.108 g, 1 mmol) were dissolved in ethanol (5 ml) respectively at room temperature. Then the two solutions were mixed and stirred slowly for about 30 min. Finally, the yellow ligand was synthesized. Then Eu(NO₃)₂.3H₂O (0.400 g, 1 mmol) in ethanol (5 ml) was added to it with stirring homogeneously. Yellow crystals suitable for X-ray ananlysis were obtained by slow evaporation at room temperature over several days.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Tris[2-(2-pyridyliminomethyl)phenolato(0.67-)]europium(III) nitrate top

Crystal data top

[Eu(C₁₂H_9.33N₂O)₃]NO₃	F(000) = 2424
M_r = 806.61	D_x = 1.651 Mg m⁻³
Hexagonal, R3	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -R 3	θ = 1.9–28.4°
a = 14.0398 (12) Å	µ = 1.99 mm⁻¹
c = 28.509 (5) Å	T = 293 K
V = 4866.7 (11) Å³	Block, yellow
Z = 6	0.21 × 0.15 × 0.10 mm

Data collection top

Bruker APEXII 1K CCD area-detector diffractometer	2599 independent reflections
Radiation source: fine-focus sealed tube	1711 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.092
ϕ and ω scans	θ_max = 28.4°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→18
T_min = 0.706, T_max = 0.819	k = −18→18
10540 measured reflections	l = −37→35

Refinement top

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.059P)²] where P = (F_o² + 2F_c²)/3
2599 reflections	(Δ/σ)_max < 0.001
155 parameters	Δρ_max = 1.11 e Å⁻³
0 restraints	Δρ_min = −0.90 e Å⁻³

Crystal data top

[Eu(C₁₂H_9.33N₂O)₃]NO₃	Z = 6
M_r = 806.61	Mo Kα radiation
Hexagonal, R3	µ = 1.99 mm⁻¹
a = 14.0398 (12) Å	T = 293 K
c = 28.509 (5) Å	0.21 × 0.15 × 0.10 mm
V = 4866.7 (11) Å³

Data collection top

Bruker APEXII 1K CCD area-detector diffractometer	2599 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	1711 reflections with I > 2σ(I)
T_min = 0.706, T_max = 0.819	R_int = 0.092
10540 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.128	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 1.11 e Å⁻³
2599 reflections	Δρ_min = −0.90 e Å⁻³
155 parameters

Special details top

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	1.0000	0.0000	0.16281 (2)	0.0373 (2)
O1	1.0522 (4)	0.1495 (3)	0.21296 (15)	0.0466 (11)
H1B	1.108 (11)	0.139 (10)	0.206 (4)	0.05 (3)*	0.33
O2	0.977 (3)	0.068 (2)	0.3090 (13)	0.558 (19)
N1	1.1365 (4)	0.0071 (4)	0.09543 (18)	0.0450 (12)
N2	1.1941 (4)	0.1521 (4)	0.14418 (17)	0.0404 (12)
N3	1.0000	0.0000	0.3159 (6)	0.142 (7)
C1	1.1473 (6)	−0.0492 (6)	0.0603 (2)	0.062 (2)
H1A	1.0877	−0.1170	0.0520	0.075*
C2	1.2458 (7)	−0.0091 (7)	0.0357 (3)	0.068 (2)
H2A	1.2515	−0.0495	0.0111	0.081*
C3	1.3364 (6)	0.0926 (6)	0.0483 (2)	0.0623 (19)
H3A	1.4029	0.1202	0.0324	0.075*
C4	1.3251 (5)	0.1502 (5)	0.0842 (2)	0.0505 (16)
H4A	1.3841	0.2173	0.0936	0.061*
C5	1.2233 (5)	0.1064 (5)	0.1066 (2)	0.0453 (15)
C6	1.2517 (5)	0.2543 (5)	0.1551 (2)	0.0460 (16)
H6A	1.3151	0.2975	0.1377	0.055*
C7	1.2259 (5)	0.3067 (5)	0.1920 (2)	0.0404 (14)
C8	1.1301 (5)	0.2504 (5)	0.2202 (2)	0.0398 (14)
C9	1.1213 (5)	0.3104 (6)	0.2584 (2)	0.0536 (17)
H9A	1.0619	0.2753	0.2787	0.064*
C10	1.1979 (6)	0.4187 (6)	0.2661 (3)	0.070 (2)
H10A	1.1888	0.4552	0.2914	0.084*
C11	1.2886 (6)	0.4749 (6)	0.2370 (3)	0.070 (2)
H11A	1.3391	0.5488	0.2420	0.084*
C12	1.3017 (5)	0.4186 (5)	0.2009 (3)	0.0581 (18)
H12A	1.3626	0.4553	0.1814	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Eu1	0.0340 (2)	0.0340 (2)	0.0438 (3)	0.01701 (11)	0.000	0.000
O1	0.041 (2)	0.040 (2)	0.055 (3)	0.018 (2)	0.008 (2)	−0.001 (2)
O2	0.46 (3)	0.34 (3)	1.02 (6)	0.30 (2)	−0.05 (5)	0.03 (4)
N1	0.040 (3)	0.047 (3)	0.045 (3)	0.019 (3)	0.005 (2)	−0.006 (2)
N2	0.033 (3)	0.036 (3)	0.050 (3)	0.016 (2)	0.002 (2)	−0.006 (2)
N3	0.180 (12)	0.180 (12)	0.065 (9)	0.090 (6)	0.000	0.000
C1	0.066 (5)	0.054 (4)	0.060 (5)	0.024 (4)	0.004 (4)	−0.018 (4)
C2	0.086 (6)	0.087 (6)	0.048 (4)	0.055 (5)	0.000 (4)	−0.014 (4)
C3	0.061 (5)	0.069 (5)	0.063 (5)	0.036 (4)	0.008 (4)	−0.001 (4)
C4	0.047 (4)	0.053 (4)	0.056 (4)	0.029 (3)	0.000 (3)	0.001 (3)
C5	0.041 (4)	0.049 (4)	0.052 (4)	0.027 (3)	0.001 (3)	0.000 (3)
C6	0.034 (3)	0.035 (3)	0.062 (4)	0.012 (3)	0.001 (3)	0.000 (3)
C7	0.040 (3)	0.033 (3)	0.047 (4)	0.018 (3)	−0.002 (3)	−0.003 (3)
C8	0.038 (3)	0.039 (3)	0.046 (4)	0.022 (3)	−0.003 (3)	0.000 (3)
C9	0.049 (4)	0.060 (4)	0.053 (4)	0.028 (4)	−0.001 (3)	−0.018 (3)
C10	0.060 (5)	0.061 (5)	0.086 (6)	0.029 (4)	−0.009 (4)	−0.035 (4)
C11	0.057 (5)	0.042 (4)	0.098 (6)	0.016 (4)	−0.004 (4)	−0.021 (4)
C12	0.043 (4)	0.042 (4)	0.078 (5)	0.013 (3)	−0.004 (4)	−0.011 (4)

Geometric parameters (Å, º) top

Eu1—O1	2.334 (4)	C1—C2	1.395 (10)
Eu1—O1ⁱ	2.334 (4)	C1—H1A	0.9300
Eu1—O1ⁱⁱ	2.334 (4)	C2—C3	1.403 (10)
Eu1—N2ⁱ	2.539 (5)	C2—H2A	0.9300
Eu1—N2ⁱⁱ	2.539 (5)	C3—C4	1.361 (9)
Eu1—N2	2.539 (5)	C3—H3A	0.9300
Eu1—N1ⁱⁱ	2.680 (5)	C4—C5	1.397 (9)
Eu1—N1ⁱ	2.680 (5)	C4—H4A	0.9300
Eu1—N1	2.680 (5)	C6—C7	1.430 (8)
Eu1—C5ⁱⁱ	3.154 (6)	C6—H6A	0.9300
Eu1—C5ⁱ	3.154 (6)	C7—C12	1.412 (8)
Eu1—C5	3.154 (6)	C7—C8	1.420 (8)
O1—C8	1.302 (7)	C8—C9	1.418 (8)
O1—H1B	0.89 (14)	C9—C10	1.372 (9)
O2—N3	1.167 (16)	C9—H9A	0.9300
N1—C1	1.330 (8)	C10—C11	1.389 (10)
N1—C5	1.353 (8)	C10—H10A	0.9300
N2—C6	1.285 (7)	C11—C12	1.365 (9)
N2—C5	1.411 (7)	C11—H11A	0.9300
N3—O2ⁱ	1.167 (16)	C12—H12A	0.9300
N3—O2ⁱⁱ	1.167 (16)

O1—Eu1—O1ⁱ	86.41 (15)	O1ⁱ—Eu1—H1B	101 (4)
O1—Eu1—O1ⁱⁱ	86.41 (15)	O1ⁱⁱ—Eu1—H1B	71 (3)
O1ⁱ—Eu1—O1ⁱⁱ	86.41 (15)	N2ⁱ—Eu1—H1B	102 (4)
O1—Eu1—N2ⁱ	80.87 (15)	N2ⁱⁱ—Eu1—H1B	140 (3)
O1ⁱ—Eu1—N2ⁱ	69.51 (15)	N2—Eu1—H1B	52 (4)
O1ⁱⁱ—Eu1—N2ⁱ	153.28 (16)	N1ⁱⁱ—Eu1—H1B	167 (3)
O1—Eu1—N2ⁱⁱ	153.28 (16)	N1ⁱ—Eu1—H1B	92 (3)
O1ⁱ—Eu1—N2ⁱⁱ	80.87 (15)	N1—Eu1—H1B	102 (4)
O1ⁱⁱ—Eu1—N2ⁱⁱ	69.51 (15)	C5ⁱⁱ—Eu1—H1B	166 (4)
N2ⁱ—Eu1—N2ⁱⁱ	115.74 (7)	C5ⁱ—Eu1—H1B	97 (3)
O1—Eu1—N2	69.51 (15)	C5—Eu1—H1B	77 (4)
O1ⁱ—Eu1—N2	153.28 (16)	C8—O1—Eu1	142.2 (4)
O1ⁱⁱ—Eu1—N2	80.87 (15)	C8—O1—H1B	83 (8)
N2ⁱ—Eu1—N2	115.74 (8)	Eu1—O1—H1B	68 (8)
N2ⁱⁱ—Eu1—N2	115.74 (7)	C1—N1—C5	118.6 (6)
O1—Eu1—N1ⁱⁱ	151.37 (16)	C1—N1—Eu1	144.0 (4)
O1ⁱ—Eu1—N1ⁱⁱ	86.02 (16)	C5—N1—Eu1	97.4 (4)
O1ⁱⁱ—Eu1—N1ⁱⁱ	120.57 (15)	C6—N2—C5	121.9 (5)
N2ⁱ—Eu1—N1ⁱⁱ	70.61 (15)	C6—N2—Eu1	134.4 (4)
N2ⁱⁱ—Eu1—N1ⁱⁱ	51.09 (15)	C5—N2—Eu1	102.1 (3)
N2—Eu1—N1ⁱⁱ	120.68 (15)	O2ⁱ—N3—O2	117.2 (12)
O1—Eu1—N1ⁱ	86.02 (16)	O2ⁱ—N3—O2ⁱⁱ	117.2 (12)
O1ⁱ—Eu1—N1ⁱ	120.57 (15)	O2—N3—O2ⁱⁱ	117.2 (12)
O1ⁱⁱ—Eu1—N1ⁱ	151.37 (16)	N1—C1—C2	121.5 (7)
N2ⁱ—Eu1—N1ⁱ	51.09 (15)	N1—C1—H1A	119.2
N2ⁱⁱ—Eu1—N1ⁱ	120.68 (15)	C2—C1—H1A	119.2
N2—Eu1—N1ⁱ	70.61 (15)	C1—C2—C3	119.6 (6)
N1ⁱⁱ—Eu1—N1ⁱ	74.31 (17)	C1—C2—H2A	120.2
O1—Eu1—N1	120.57 (15)	C3—C2—H2A	120.2
O1ⁱ—Eu1—N1	151.37 (16)	C4—C3—C2	118.8 (7)
O1ⁱⁱ—Eu1—N1	86.02 (16)	C4—C3—H3A	120.6
N2ⁱ—Eu1—N1	120.68 (15)	C2—C3—H3A	120.6
N2ⁱⁱ—Eu1—N1	70.61 (15)	C3—C4—C5	118.7 (6)
N2—Eu1—N1	51.09 (15)	C3—C4—H4A	120.7
N1ⁱⁱ—Eu1—N1	74.31 (17)	C5—C4—H4A	120.7
N1ⁱ—Eu1—N1	74.31 (17)	N1—C5—C4	122.8 (6)
O1—Eu1—C5ⁱⁱ	168.10 (15)	N1—C5—N2	109.3 (5)
O1ⁱ—Eu1—C5ⁱⁱ	81.98 (16)	C4—C5—N2	127.9 (6)
O1ⁱⁱ—Eu1—C5ⁱⁱ	95.44 (15)	N1—C5—Eu1	57.4 (3)
N2ⁱ—Eu1—C5ⁱⁱ	92.55 (15)	C4—C5—Eu1	175.7 (5)
N2ⁱⁱ—Eu1—C5ⁱⁱ	25.94 (15)	N2—C5—Eu1	51.9 (3)
N2—Eu1—C5ⁱⁱ	122.40 (15)	N2—C6—C7	125.0 (6)
N1ⁱⁱ—Eu1—C5ⁱⁱ	25.18 (15)	N2—C6—H6A	117.5
N1ⁱ—Eu1—C5ⁱⁱ	97.61 (16)	C7—C6—H6A	117.5
N1—Eu1—C5ⁱⁱ	71.32 (15)	C12—C7—C8	119.7 (6)
O1—Eu1—C5ⁱ	81.98 (16)	C12—C7—C6	117.4 (6)
O1ⁱ—Eu1—C5ⁱ	95.44 (16)	C8—C7—C6	122.9 (5)
O1ⁱⁱ—Eu1—C5ⁱ	168.10 (15)	O1—C8—C9	119.5 (6)
N2ⁱ—Eu1—C5ⁱ	25.94 (15)	O1—C8—C7	124.2 (5)
N2ⁱⁱ—Eu1—C5ⁱ	122.40 (15)	C9—C8—C7	116.3 (5)
N2—Eu1—C5ⁱ	92.55 (15)	O1—C8—H1B	36 (5)
N1ⁱⁱ—Eu1—C5ⁱ	71.32 (15)	C9—C8—H1B	143 (5)
N1ⁱ—Eu1—C5ⁱ	25.18 (15)	C7—C8—H1B	94 (5)
N1—Eu1—C5ⁱ	97.61 (16)	C10—C9—C8	121.9 (7)
C5ⁱⁱ—Eu1—C5ⁱ	96.46 (15)	C10—C9—H9A	119.0
O1—Eu1—C5	95.44 (16)	C8—C9—H9A	119.0
O1ⁱ—Eu1—C5	168.10 (15)	C9—C10—C11	121.4 (7)
O1ⁱⁱ—Eu1—C5	81.98 (16)	C9—C10—H10A	119.3
N2ⁱ—Eu1—C5	122.40 (15)	C11—C10—H10A	119.3
N2ⁱⁱ—Eu1—C5	92.55 (15)	C12—C11—C10	118.2 (6)
N2—Eu1—C5	25.94 (15)	C12—C11—H11A	120.9
N1ⁱⁱ—Eu1—C5	97.61 (16)	C10—C11—H11A	120.9
N1ⁱ—Eu1—C5	71.32 (15)	C11—C12—C7	122.3 (7)
N1—Eu1—C5	25.18 (15)	C11—C12—H12A	118.8
C5ⁱⁱ—Eu1—C5	96.46 (15)	C7—C12—H12A	118.8
C5ⁱ—Eu1—C5	96.46 (15)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1B···N2	0.89 (14)	2.09 (14)	2.783 (6)	134 (11)
C12—H12A···Cg1ⁱⁱⁱ	0.93	2.88	3.788 (9)	167

Symmetry code: (iii) x−y+2/3, x−2/3, −z+1/3.

Experimental details

Crystal data
Chemical formula	[Eu(C₁₂H_9.33N₂O)₃]NO₃
M_r	806.61
Crystal system, space group	Hexagonal, R3
Temperature (K)	293
a, c (Å)	14.0398 (12), 28.509 (5)
V (Å³)	4866.7 (11)
Z	6
Radiation type	Mo Kα
µ (mm⁻¹)	1.99
Crystal size (mm)	0.21 × 0.15 × 0.10

Data collection
Diffractometer	Bruker APEXII 1K CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.706, 0.819
No. of measured, independent and observed [I > 2σ(I)] reflections	10540, 2599, 1711
R_int	0.092
(sin θ/λ)_max (Å⁻¹)	0.670

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.128, 1.00
No. of reflections	2599
No. of parameters	155
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	1.11, −0.90

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Eu1—O1	2.334 (4)	Eu1—N2	2.539 (5)
Eu1—O1ⁱ	2.334 (4)	Eu1—N1ⁱⁱ	2.680 (5)
Eu1—O1ⁱⁱ	2.334 (4)	Eu1—N1ⁱ	2.680 (5)
Eu1—N2ⁱ	2.539 (5)	Eu1—N1	2.680 (5)
Eu1—N2ⁱⁱ	2.539 (5)

O1—Eu1—O1ⁱ	86.41 (15)	O1—Eu1—N1ⁱⁱ	151.37 (16)
O1—Eu1—O1ⁱⁱ	86.41 (15)	N2—Eu1—N1ⁱⁱ	120.68 (15)
O1—Eu1—N2ⁱ	80.87 (15)	O1—Eu1—N1ⁱ	86.02 (16)
O1—Eu1—N2ⁱⁱ	153.28 (16)	N2—Eu1—N1ⁱ	70.61 (15)
O1—Eu1—N2	69.51 (15)	O1—Eu1—N1	120.57 (15)
O1ⁱ—Eu1—N2	153.28 (16)	N2—Eu1—N1	51.09 (15)
O1ⁱⁱ—Eu1—N2	80.87 (15)	N1ⁱⁱ—Eu1—N1	74.31 (17)
N2ⁱ—Eu1—N2	115.74 (8)	N1ⁱ—Eu1—N1	74.31 (17)
N2ⁱⁱ—Eu1—N2	115.74 (7)	O1—Eu1—C5ⁱⁱ	168.10 (15)