Tris(1-ethyl-3-methyl­imidazolium) hexa­bromidoeuropate(III)

Pellens, M.; Thijs, B.; Van Hecke, K.; Van Meervelt, L.; Binnemans, K.; Nockemann, P.

doi:10.1107/S1600536808018382

metal-organic compounds

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ISSN: 2056-9890

Volume 64| Part 7| July 2008| Page m945

doi:10.1107/S1600536808018382

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Tris(1-ethyl-3-methylimidazolium) hexabromidoeuropate(III)

Michael Pellens,^a Ben Thijs,^a Kristof Van Hecke,^b Luc Van Meervelt,^b Koen Binnemans ^a and Peter Nockemann ^a ^*

^aLaboratory of Coordination Chemistry, Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F bus 2404, B-3001 Leuven, Belgium, and ^bLaboratory of Biomolecular Architecture, Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F bus 2404, B-3001 Leuven, Belgium
^*Correspondence e-mail: peter.nockemann@chem.kuleuven.be

(Received 30 April 2008; accepted 17 June 2008; online 21 June 2008)

The crystal structure of the title compound, (C₆H₁₁N₂)₃[EuBr₆], consists of 1-ethyl-3-methylimidazolium cations and centrosymmetric octahedral hexabromidoeuropate anions. The [EuBr₆]³⁻ anions are located at the corners and face-centres of the monoclinic unit cell. Characteristic hydrogen-bonding interactions can be observed between the bromide anions and the acidic H atoms of the imidazolium cations.

Related literature

For related literature, see: Arenz et al. (2005 ); Binnemans (2007 ); Chaumont & Wipff (2003 ); Driesen et al. (2004 ); Matsumoto et al. (2002 ); Nockemann et al. (2005 , 2006 , 2008 ); Reichert et al. (2006 ); Taubert (2004 ); Tsuda et al. (2001 ); Zhao et al. (2004 ).

Experimental

Crystal data

(C₆H₁₁N₂)₃[EuBr₆]
M_r = 964.87
Monoclinic, P 2₁ /c
a = 15.765 (1) Å
b = 12.729 (1) Å
c = 14.920 (1) Å
β = 90.36 (1)°
V = 2994.0 (4) Å³
Z = 4
Mo Kα radiation
μ = 10.12 mm⁻¹
T = 100 (2) K
0.18 × 0.17 × 0.16 mm

Data collection

Oxford Diffraction Gemini A Ultra diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ) T_min = 0.148, T_max = 0.200
17678 measured reflections
7019 independent reflections
5043 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.099
S = 1.07
7019 reflections
290 parameters
H-atom parameters constrained
Δρ_max = 1.75 e Å⁻³
Δρ_min = −1.44 e Å⁻³

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, Oxfordshire, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007 ); software used to prepare material for publication: PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808018382/hg2399sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808018382/hg2399Isup2.hkl

checkCIF report

Comment top

Ionic liquids are increasingly attracting the attention of inorganic and materials chemists (Taubert, 2004; Reichert et al., 2006; Nockemann et al., 2008). Lanthanide compounds dissolved in ionic liquids have been of interest especially due to their photoluminescence behavior (Driesen et al., 2004; Binnemans, 2007; Nockemann et al., 2005). Experimental and theoretical studies on lanthanide ions in halide containing imidazolium ionic liquids have been investigated regarding electrochemical and spectroscopic properties (Arenz et al., 2005; Chaumont & Wipff, 2003; Tsuda et al., 2001). Imidazolium cations have been reported to yield low-melting lanthanide-containing ionic liquids like [BMIM]₅[Eu(SCN)₈] (Nockemann et al., 2006). An analogue structure to the title compound, [EMIM]₃[LaCl₆], has been reported previously (Matsumoto et al., 2002). The title compound crystallized unexpectedly after dissolving europium bis(trifluoromethylsulfonyl)imide hexahydrate, Eu(Tf₂N)₃.6H₂O in a mixture of [EMIM]Br and a nitrile functionalized imidazolium ionic liquid, 1-butyronitrile-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [C₃CNMIM][Tf₂N]. The crystal structure of [EMIM]₃[EuBr₆] (Fig. 1) consists of 1-ethyl-3-methylimidazolium cations and octahedral [EuBr₆]^3- anions. The Eu—Br distances are in the range of 2.7793 (6) Å to 2.8187 (6) Å. The octahedral geometry of the two crystallographically independent [EuBr₆]^3- anions is slightly distorted with the surrounding of Eu1 more distorted than Eu2 with Br—Eu—Br angles ranging from 86.90 (2)° to 93.10 (2)° for Eu1, compared to angles ranging from 89.11 (2)° to 90.89 (2)° for Eu2. All bromine anions exhibit short contacts to neighboring H-atoms of imidazolium rings ranging from 2.76 Å to 2.90 Å. All three H-atoms of each of the three crystallographically independent imidazolium cations form hydrogen bonds with bromide atoms, which is exemplarily shown in Fig. 2 for one cation. In the packing of [EMIM]₃[EuBr₆], the [EuBr₆]^3- anions are located on the corners and face-centers of the monoclinic unit cell (Fig. 3).

Related literature top

For related literature, see: Arenz et al. (2005); Binnemans (2007); Chaumont & Wipff (2003); Driesen et al. (2004); Matsumoto et al. (2002); Nockemann et al. (2005, 2006, 2008); Reichert et al. (2006); Taubert (2004); Tsuda et al. (2001); Zhao et al. (2004).

Experimental top

[EMIM]₃[EuBr₆] crystallized unintentionally after dissolving europium(III) bis(trifluoromethylsulfonyl)imide hexahydrate, Eu(Tf₂N)₃.6H₂O (0.5 g, 0.454 mmol) in a mixture of 5 ml of [EMIM]Br and 5 ml of a nitrile functionalized imidazolium ionic liquid, 1-butyronitrile-3-methylimidazolium bis(trifluoromethylsulfonyl)imide, [C₃CNMIM][Tf₂N]. [EMIM]Br was purchased from IoLiTec. The nitrile functionalized imidazolium ionic liquid has been synthesized following a procedure that has been reported in the literature (Zhao et al. 2004). The title compound crystallized as small slightly yellow blocks.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis RED (Oxford Diffraction, 2008); data reduction: CrysAlis RED (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2007); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top

	Fig. 1. Structure of the [EuBr₆]^3- anion and interactions to two exemplary [EMIM]⁺ cations around Eu1 in the crystal structure of [EMIM]₃[EuBr₆]. The dashed lines indicate the hydrogen bonding interactions. Displacement ellipsoids are shown at the 50% probability level and H-atoms are drawn as small circles of arbitrary radii.
	Fig. 2. Surrounding of an [EMIM]⁺ cation in the crystal structure of [EMIM]₃[EuBr₆]. The dashed lines indicate the hydrogen bonding interactions. Displacement ellipsoids are shown at the 50% probability level and H-atoms are drawn as small circles of arbitrary radii.
	Fig. 3. Packing of the structure of [EMIM]₃[EuBr₆] viewed along the b axis. The [EuBr₆]^3- anions are located on the corners and face-centers of the monoclinic unit cell.

Tris(1-ethyl-3-methylimidazolium) hexabromidoeuropate(III) top

Crystal data top

(C₆H₁₁N₂)₃[EuBr₆]	F(000) = 1824
M_r = 964.87	D_x = 2.141 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9203 reflections
a = 15.765 (1) Å	θ = 3.0–29.1°
b = 12.729 (1) Å	µ = 10.12 mm⁻¹
c = 14.920 (1) Å	T = 100 K
β = 90.36 (1)°	Block, yellow
V = 2994.0 (4) Å³	0.18 × 0.17 × 0.16 mm
Z = 4

Data collection top

Oxford Diffraction Gemini A Ultra diffractometer	7019 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5043 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
Detector resolution: 10.3310 pixels mm^-1	θ_max = 29.1°, θ_min = 3.0°
ω and ϕ scans	h = −21→13
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −14→17
T_min = 0.148, T_max = 0.200	l = −19→19
17678 measured reflections

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0541P)²] where P = (F_o² + 2F_c²)/3
7019 reflections	(Δ/σ)_max < 0.001
290 parameters	Δρ_max = 1.75 e Å⁻³
0 restraints	Δρ_min = −1.44 e Å⁻³

Crystal data top

(C₆H₁₁N₂)₃[EuBr₆]	V = 2994.0 (4) Å³
M_r = 964.87	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 15.765 (1) Å	µ = 10.12 mm⁻¹
b = 12.729 (1) Å	T = 100 K
c = 14.920 (1) Å	0.18 × 0.17 × 0.16 mm
β = 90.36 (1)°

Data collection top

Oxford Diffraction Gemini A Ultra diffractometer	7019 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	5043 reflections with I > 2σ(I)
T_min = 0.148, T_max = 0.200	R_int = 0.029
17678 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 1.07	Δρ_max = 1.75 e Å⁻³
7019 reflections	Δρ_min = −1.44 e Å⁻³
290 parameters

Special details top

Experimental. CrysAlis RED (CrysAlis RED, 2008). 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.

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

	x	y	z	U_iso*/U_eq
C1	0.9054 (4)	0.1566 (5)	0.4127 (4)	0.0200 (14)
H1	0.9361	0.2068	0.4471	0.024*
C2	0.8011 (5)	0.0618 (5)	0.3547 (4)	0.0257 (15)
H2	0.7459	0.0348	0.3428	0.031*
C3	0.8726 (4)	0.0310 (5)	0.3170 (4)	0.0228 (14)
H3	0.8781	−0.0218	0.2725	0.027*
C4	1.0300 (4)	0.0820 (5)	0.3349 (4)	0.0171 (13)
H4A	1.0576	0.1500	0.3491	0.021*
H4B	1.0379	0.0680	0.2702	0.021*
C5	1.0725 (4)	−0.0044 (5)	0.3889 (4)	0.0212 (14)
H5A	1.0614	0.0064	0.4528	0.032*
H5B	1.1338	−0.0029	0.3785	0.032*
H5C	1.0497	−0.0727	0.3703	0.032*
C6	0.7598 (4)	0.2016 (5)	0.4680 (4)	0.0270 (16)
H6A	0.7428	0.1604	0.5204	0.041*
H6B	0.7098	0.2169	0.4309	0.041*
H6C	0.7858	0.2676	0.4880	0.041*
C7	0.6503 (4)	0.3160 (6)	0.2301 (4)	0.0235 (15)
H7	0.5922	0.3054	0.2159	0.028*
C8	0.7896 (4)	0.2961 (5)	0.2383 (4)	0.0243 (15)
H8	0.8454	0.2696	0.2309	0.029*
C9	0.7664 (4)	0.3830 (5)	0.2844 (4)	0.0217 (14)
H9	0.8039	0.4287	0.3156	0.026*
C10	0.6311 (5)	0.4800 (6)	0.3179 (4)	0.0306 (17)
H10A	0.5807	0.4923	0.2794	0.037*
H10B	0.6650	0.5455	0.3189	0.037*
C11	0.6025 (5)	0.4553 (6)	0.4115 (5)	0.0358 (18)
H11A	0.5715	0.3886	0.4114	0.054*
H11B	0.5653	0.5115	0.4329	0.054*
H11C	0.6521	0.4497	0.4512	0.054*
C12	0.7057 (5)	0.1584 (5)	0.1507 (4)	0.0291 (16)
H12A	0.6658	0.1111	0.1805	0.044*
H12B	0.7607	0.1233	0.1444	0.044*
H12C	0.6836	0.1769	0.0912	0.044*
C13	0.7070 (4)	0.8020 (5)	0.3480 (4)	0.0272 (15)
H13	0.6671	0.8381	0.3841	0.033*
C14	0.8247 (5)	0.7279 (7)	0.3036 (5)	0.042 (2)
H14	0.8813	0.7024	0.3025	0.051*
C15	0.7644 (4)	0.7205 (7)	0.2371 (5)	0.037 (2)
H15	0.7720	0.6888	0.1800	0.045*
C16	0.6146 (5)	0.7797 (6)	0.2138 (5)	0.0376 (18)
H16A	0.5698	0.8121	0.2508	0.045*
H16B	0.5942	0.7100	0.1937	0.045*
C17	0.6318 (5)	0.8486 (6)	0.1327 (5)	0.045 (2)
H17A	0.6572	0.9150	0.1524	0.068*
H17B	0.5783	0.8629	0.1011	0.068*
H17C	0.6709	0.8123	0.0923	0.068*
C18	0.8275 (5)	0.8070 (6)	0.4594 (4)	0.0316 (17)
H18A	0.7897	0.8504	0.4959	0.047*
H18B	0.8800	0.8458	0.4476	0.047*
H18C	0.8410	0.7421	0.4917	0.047*
N1	0.9384 (3)	0.0896 (4)	0.3541 (3)	0.0166 (11)
N2	0.8220 (3)	0.1409 (4)	0.4148 (3)	0.0141 (10)
N3	0.6826 (4)	0.3942 (4)	0.2789 (3)	0.0281 (13)
N4	0.7163 (3)	0.2543 (4)	0.2045 (3)	0.0194 (11)
N5	0.6912 (4)	0.7670 (4)	0.2673 (4)	0.0294 (13)
N6	0.7846 (4)	0.7809 (4)	0.3727 (4)	0.0273 (13)
Br1	0.99929 (4)	0.37839 (5)	0.34343 (4)	0.01889 (14)
Br2	0.82537 (4)	0.52642 (5)	0.48677 (4)	0.02342 (15)
Br3	1.03396 (4)	0.68086 (5)	0.39729 (4)	0.01711 (14)
Br4	0.33611 (4)	0.02950 (5)	0.43034 (4)	0.01855 (14)
Br5	0.50481 (4)	0.21190 (5)	0.54969 (4)	0.02105 (14)
Br6	0.56634 (4)	0.05083 (5)	0.33129 (4)	0.02125 (15)
Eu1	1.0000	0.5000	0.5000	0.00923 (9)
Eu2	0.5000	0.0000	0.5000	0.01018 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.031 (4)	0.013 (3)	0.015 (3)	−0.001 (3)	0.008 (3)	0.003 (2)
C2	0.036 (4)	0.017 (3)	0.024 (3)	−0.003 (3)	0.003 (3)	−0.004 (3)
C3	0.025 (3)	0.018 (3)	0.026 (3)	0.000 (3)	0.004 (3)	−0.007 (3)
C4	0.017 (3)	0.021 (3)	0.014 (3)	−0.001 (3)	0.000 (2)	0.000 (3)
C5	0.014 (3)	0.021 (3)	0.029 (3)	0.001 (3)	−0.003 (3)	0.002 (3)
C6	0.036 (4)	0.018 (3)	0.028 (3)	0.005 (3)	0.015 (3)	−0.005 (3)
C7	0.016 (3)	0.039 (4)	0.015 (3)	0.000 (3)	−0.006 (2)	0.004 (3)
C8	0.028 (4)	0.026 (4)	0.019 (3)	−0.004 (3)	−0.001 (3)	0.005 (3)
C9	0.023 (3)	0.026 (4)	0.017 (3)	−0.005 (3)	−0.008 (3)	0.002 (3)
C10	0.036 (4)	0.028 (4)	0.028 (4)	0.013 (3)	−0.003 (3)	0.002 (3)
C11	0.026 (4)	0.047 (5)	0.035 (4)	−0.003 (3)	0.006 (3)	−0.009 (4)
C12	0.043 (4)	0.023 (4)	0.021 (3)	−0.005 (3)	0.009 (3)	−0.004 (3)
C13	0.029 (4)	0.027 (4)	0.026 (3)	−0.001 (3)	0.000 (3)	−0.007 (3)
C14	0.050 (5)	0.054 (6)	0.023 (4)	0.023 (4)	0.000 (3)	−0.014 (4)
C15	0.014 (3)	0.063 (6)	0.035 (4)	0.015 (3)	−0.005 (3)	−0.014 (4)
C16	0.029 (4)	0.037 (5)	0.047 (5)	0.004 (3)	−0.009 (3)	−0.017 (4)
C17	0.054 (5)	0.044 (5)	0.037 (4)	0.000 (4)	−0.026 (4)	−0.005 (4)
C18	0.036 (4)	0.034 (4)	0.025 (3)	0.012 (3)	−0.007 (3)	−0.008 (3)
N1	0.017 (3)	0.016 (3)	0.017 (2)	−0.002 (2)	0.001 (2)	−0.002 (2)
N2	0.009 (2)	0.017 (3)	0.016 (2)	−0.001 (2)	0.0001 (19)	−0.004 (2)
N3	0.044 (4)	0.021 (3)	0.019 (3)	0.003 (3)	0.006 (3)	0.000 (2)
N4	0.019 (3)	0.026 (3)	0.014 (2)	−0.004 (2)	0.002 (2)	0.001 (2)
N5	0.030 (3)	0.023 (3)	0.036 (3)	−0.004 (3)	0.005 (3)	−0.007 (3)
N6	0.034 (3)	0.021 (3)	0.027 (3)	0.010 (3)	0.008 (3)	0.000 (2)
Br1	0.0281 (3)	0.0149 (3)	0.0137 (3)	−0.0037 (3)	0.0016 (2)	−0.0014 (2)
Br2	0.0153 (3)	0.0261 (4)	0.0288 (3)	0.0010 (3)	−0.0015 (3)	−0.0004 (3)
Br3	0.0229 (3)	0.0138 (3)	0.0146 (3)	−0.0018 (2)	−0.0001 (2)	0.0010 (2)
Br4	0.0137 (3)	0.0225 (3)	0.0195 (3)	0.0012 (2)	−0.0022 (2)	0.0004 (3)
Br5	0.0235 (3)	0.0168 (3)	0.0228 (3)	−0.0011 (3)	−0.0039 (2)	0.0003 (3)
Br6	0.0185 (3)	0.0301 (4)	0.0152 (3)	−0.0005 (3)	0.0030 (2)	0.0040 (3)
Eu1	0.01068 (18)	0.00812 (19)	0.00889 (18)	−0.00080 (16)	−0.00038 (14)	0.00018 (15)
Eu2	0.00931 (18)	0.0124 (2)	0.00889 (18)	0.00017 (16)	0.00048 (14)	0.00114 (16)

Geometric parameters (Å, º) top

C1—N1	1.329 (7)	C12—H12A	0.9800
C1—N2	1.331 (8)	C12—H12B	0.9800
C1—H1	0.9500	C12—H12C	0.9800
C2—C3	1.322 (9)	C13—N6	1.304 (9)
C2—N2	1.388 (8)	C13—N5	1.306 (8)
C2—H2	0.9500	C13—H13	0.9500
C3—N1	1.390 (8)	C14—C15	1.373 (10)
C3—H3	0.9500	C14—N6	1.387 (8)
C4—N1	1.478 (7)	C14—H14	0.9500
C4—C5	1.517 (8)	C15—N5	1.375 (8)
C4—H4A	0.9900	C15—H15	0.9500
C4—H4B	0.9900	C16—N5	1.452 (9)
C5—H5A	0.9800	C16—C17	1.520 (11)
C5—H5B	0.9800	C16—H16A	0.9900
C5—H5C	0.9800	C16—H16B	0.9900
C6—N2	1.482 (7)	C17—H17A	0.9800
C6—H6A	0.9800	C17—H17B	0.9800
C6—H6B	0.9800	C17—H17C	0.9800
C6—H6C	0.9800	C18—N6	1.495 (9)
C7—N3	1.332 (8)	C18—H18A	0.9800
C7—N4	1.360 (8)	C18—H18B	0.9800
C7—H7	0.9500	C18—H18C	0.9800
C8—C9	1.355 (9)	Br1—Eu1	2.8024 (6)
C8—N4	1.365 (8)	Br2—Eu1	2.7793 (6)
C8—H8	0.9500	Br3—Eu1	2.8188 (6)
C9—N3	1.330 (8)	Br4—Eu2	2.8041 (6)
C9—H9	0.9500	Br5—Eu2	2.7982 (6)
C10—N3	1.483 (8)	Br6—Eu2	2.8074 (5)
C10—C11	1.503 (9)	Eu1—Br2ⁱ	2.7794 (6)
C10—H10A	0.9900	Eu1—Br1ⁱ	2.8023 (6)
C10—H10B	0.9900	Eu1—Br3ⁱ	2.8187 (6)
C11—H11A	0.9800	Eu2—Br5ⁱⁱ	2.7982 (6)
C11—H11B	0.9800	Eu2—Br4ⁱⁱ	2.8041 (6)
C11—H11C	0.9800	Eu2—Br6ⁱⁱ	2.8073 (5)
C12—N4	1.470 (8)

N1—C1—N2	108.1 (5)	C17—C16—H16A	109.6
N1—C1—H1	125.9	N5—C16—H16B	109.6
N2—C1—H1	125.9	C17—C16—H16B	109.6
C3—C2—N2	106.8 (6)	H16A—C16—H16B	108.1
C3—C2—H2	126.6	C16—C17—H17A	109.5
N2—C2—H2	126.6	C16—C17—H17B	109.5
C2—C3—N1	108.0 (6)	H17A—C17—H17B	109.5
C2—C3—H3	126.0	C16—C17—H17C	109.5
N1—C3—H3	126.0	H17A—C17—H17C	109.5
N1—C4—C5	111.9 (5)	H17B—C17—H17C	109.5
N1—C4—H4A	109.2	N6—C18—H18A	109.5
C5—C4—H4A	109.2	N6—C18—H18B	109.5
N1—C4—H4B	109.2	H18A—C18—H18B	109.5
C5—C4—H4B	109.2	N6—C18—H18C	109.5
H4A—C4—H4B	107.9	H18A—C18—H18C	109.5
C4—C5—H5A	109.5	H18B—C18—H18C	109.5
C4—C5—H5B	109.5	C1—N1—C3	108.2 (5)
H5A—C5—H5B	109.5	C1—N1—C4	123.8 (5)
C4—C5—H5C	109.5	C3—N1—C4	128.0 (5)
H5A—C5—H5C	109.5	C1—N2—C2	108.9 (5)
H5B—C5—H5C	109.5	C1—N2—C6	126.3 (5)
N2—C6—H6A	109.5	C2—N2—C6	124.7 (5)
N2—C6—H6B	109.5	C9—N3—C7	109.3 (5)
H6A—C6—H6B	109.5	C9—N3—C10	126.9 (6)
N2—C6—H6C	109.5	C7—N3—C10	123.8 (6)
H6A—C6—H6C	109.5	C7—N4—C8	108.5 (5)
H6B—C6—H6C	109.5	C7—N4—C12	123.2 (6)
N3—C7—N4	107.1 (5)	C8—N4—C12	128.2 (6)
N3—C7—H7	126.4	C13—N5—C15	107.1 (6)
N4—C7—H7	126.4	C13—N5—C16	128.4 (6)
C9—C8—N4	106.0 (6)	C15—N5—C16	124.3 (6)
C9—C8—H8	127.0	C13—N6—C14	108.8 (6)
N4—C8—H8	127.0	C13—N6—C18	128.1 (5)
N3—C9—C8	109.1 (6)	C14—N6—C18	123.1 (6)
N3—C9—H9	125.5	Br2—Eu1—Br2ⁱ	180.0
C8—C9—H9	125.5	Br2—Eu1—Br1ⁱ	89.496 (19)
N3—C10—C11	112.2 (6)	Br2ⁱ—Eu1—Br1ⁱ	90.505 (18)
N3—C10—H10A	109.2	Br2—Eu1—Br1	90.505 (19)
C11—C10—H10A	109.2	Br2ⁱ—Eu1—Br1	89.494 (18)
N3—C10—H10B	109.2	Br1ⁱ—Eu1—Br1	180.0
C11—C10—H10B	109.2	Br2—Eu1—Br3ⁱ	86.905 (18)
H10A—C10—H10B	107.9	Br2ⁱ—Eu1—Br3ⁱ	93.095 (18)
C10—C11—H11A	109.5	Br1ⁱ—Eu1—Br3ⁱ	89.872 (16)
C10—C11—H11B	109.5	Br1—Eu1—Br3ⁱ	90.129 (16)
H11A—C11—H11B	109.5	Br2—Eu1—Br3	93.096 (18)
C10—C11—H11C	109.5	Br2ⁱ—Eu1—Br3	86.904 (18)
H11A—C11—H11C	109.5	Br1ⁱ—Eu1—Br3	90.128 (16)
H11B—C11—H11C	109.5	Br1—Eu1—Br3	89.871 (16)
N4—C12—H12A	109.5	Br3ⁱ—Eu1—Br3	180.0
N4—C12—H12B	109.5	Br5—Eu2—Br5ⁱⁱ	180.0
H12A—C12—H12B	109.5	Br5—Eu2—Br4ⁱⁱ	90.431 (18)
N4—C12—H12C	109.5	Br5ⁱⁱ—Eu2—Br4ⁱⁱ	89.569 (18)
H12A—C12—H12C	109.5	Br5—Eu2—Br4	89.568 (18)
H12B—C12—H12C	109.5	Br5ⁱⁱ—Eu2—Br4	90.432 (18)
N6—C13—N5	111.3 (6)	Br4ⁱⁱ—Eu2—Br4	180.0
N6—C13—H13	124.4	Br5—Eu2—Br6ⁱⁱ	89.668 (18)
N5—C13—H13	124.4	Br5ⁱⁱ—Eu2—Br6ⁱⁱ	90.332 (18)
C15—C14—N6	104.7 (7)	Br4ⁱⁱ—Eu2—Br6ⁱⁱ	89.105 (17)
C15—C14—H14	127.6	Br4—Eu2—Br6ⁱⁱ	90.895 (17)
N6—C14—H14	127.6	Br5—Eu2—Br6	90.331 (18)
C14—C15—N5	108.2 (6)	Br5ⁱⁱ—Eu2—Br6	89.668 (18)
C14—C15—H15	125.9	Br4ⁱⁱ—Eu2—Br6	90.896 (17)
N5—C15—H15	125.9	Br4—Eu2—Br6	89.104 (17)
N5—C16—C17	110.5 (6)	Br6ⁱⁱ—Eu2—Br6	180.0
N5—C16—H16A	109.6

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

Experimental details

Crystal data
Chemical formula	(C₆H₁₁N₂)₃[EuBr₆]
M_r	964.87
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	15.765 (1), 12.729 (1), 14.920 (1)
β (°)	90.36 (1)
V (Å³)	2994.0 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	10.12
Crystal size (mm)	0.18 × 0.17 × 0.16

Data collection
Diffractometer	Oxford Diffraction Gemini A Ultra diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.148, 0.200
No. of measured, independent and observed [I > 2σ(I)] reflections	17678, 7019, 5043
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.099, 1.07
No. of reflections	7019
No. of parameters	290
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.75, −1.44

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2007), PLATON (Spek, 2003).

Acknowledgements

The authors acknowledge the FWO-Flanders for financial support (project No. G.0508.07). Financial support by the Katholieke Universiteit Leuven is also acknowledged (project Nos. GOA08/05 and IDO/05/005). Dr Oliver Presly from Oxford Diffraction Ltd is greatly acknowledged for the collection and processing of the diffraction data.

References

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