Tris(1-ethyl-3-methyl-imidazolium) hexa-bromidoeuropate(III).

The crystal structure of the title compound, (C(6)H(11)N(2))(3)[EuBr(6)], consists of 1-ethyl-3-methyl-imidazolium cations and centrosymmetric octa-hedral hexa-bromido-europate anions. The [EuBr(6)](3-) anions are located at the corners and face-centres of the monoclinic unit cell. Characteristic hydrogen-bonding inter-actions 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 = 964.87

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.099

S = 1.07

7019 reflections

290 parameters

H-atom parameters constrained

Δρmax = 1.75 e Å−3

Δρmin = −1.44 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); 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 ▶).

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

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

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

(C6H11N2)3[Eu1Br6]	F000 = 1824
Mr = 964.87	Dx = 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 = 3.0–29.1º
b = 12.729 (1) Å	µ = 10.12 mm−1
c = 14.920 (1) Å	T = 100 (2) K
β = 90.36 (1)º	Block, yellow
V = 2994.0 (4) Å3	0.18 × 0.17 × 0.16 mm
Z = 4

Oxford Diffraction Gemini A Ultra diffractometer	7019 independent reflections
Radiation source: Enhance (Mo) X-ray Source	5043 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.029
Detector resolution: 10.3310 pixels mm-1	θmax = 29.1º
T = 100(2) K	θmin = 3.0º
ω and φ scans	h = −21→13
Absorption correction: multi-scan(CrysAlis RED; Oxford Diffraction, 2008)	k = −14→17
Tmin = 0.148, Tmax = 0.200	l = −19→19
17678 measured reflections

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)] = 0.029	H-atom parameters constrained
wR(F2) = 0.099	w = 1/[σ2(Fo2) + (0.0541P)2] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
7019 reflections	Δρmax = 1.75 e Å−3
290 parameters	Δρmin = −1.44 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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