3,3-Dimethyl-1,1-(propane-1,3-di-yl)diimidazol-1-ium tetra-bromido-cadmate(II).

The title compound, (C(11)H(18)N(4))[CdBr(4)], was prepared by an anion exchange. The dihedral angle between the two planar imidazolium rings in the cation is 74.4 (4)°. The crystal packing is stabilized by weak inter-molecular C-H⋯Br hydrogen bonds between the cation and the tetrahedral anion, building up a three-dimensionnal network.

Related literature

For the properties and applications of ionic liquids, see: Welton (1999 ▶); Nicholas et al. (2004 ▶); Yu et al. (2007 ▶). For dicationic ionic liquids, see: Jared et al. (2005 ▶); Liang et al. (2008 ▶); Song et al. (2009 ▶); Geng et al. (2010 ▶). For related structures, see: Jared et al. (2005 ▶); Liang et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

(C11H18N4)[CdBr4]

M = 638.33

Monoclinic,

a = 8.5050 (17) Å

b = 15.876 (3) Å

c = 13.836 (3) Å

β = 96.07 (3)°

V = 1857.7 (6) Å3

Z = 4

Mo Kα radiation

μ = 9.78 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.245, T max = 0.442

3383 measured reflections

3383 independent reflections

1874 reflections with I > 2σ(I)

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.062

wR(F 2) = 0.144

S = 0.95

3383 reflections

183 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.77 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810031211/dn2593sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810031211/dn2593Isup2.hkl

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

(C11H18N4)[CdBr4]	F(000) = 1200
Mr = 638.33	Dx = 2.282 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.5050 (17) Å	θ = 9–13°
b = 15.876 (3) Å	µ = 9.78 mm−1
c = 13.836 (3) Å	T = 293 K
β = 96.07 (3)°	Block, white
V = 1857.7 (6) Å3	0.20 × 0.10 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1874 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.000
graphite	θmax = 25.3°, θmin = 2.0°
ω/2θ scans	h = −10→10
Absorption correction: ψ scan (North et al., 1968)	k = 0→19
Tmin = 0.245, Tmax = 0.442	l = 0→16
3383 measured reflections	3 standard reflections every 200 reflections
3383 independent reflections	intensity decay: 1%

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.144	H-atom parameters constrained
S = 0.95	w = 1/[σ2(Fo2) + (0.066P)2] where P = (Fo2 + 2Fc2)/3
3383 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.77 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
N1	0.2634 (10)	0.0761 (6)	0.4518 (6)	0.045 (2)
N2	0.2576 (10)	0.2095 (6)	0.4221 (7)	0.052 (2)
N3	0.5789 (10)	0.3667 (6)	0.6079 (7)	0.060 (3)
N4	0.8099 (10)	0.3936 (6)	0.6694 (6)	0.047 (2)
C1	0.2360 (16)	−0.0015 (9)	0.4950 (10)	0.095 (5)
H1A	0.2116	0.0075	0.5604	0.142*
H1B	0.3289	−0.0360	0.4959	0.142*
H1C	0.1488	−0.0293	0.4584	0.142*
C2	0.3518 (14)	0.0926 (9)	0.3730 (9)	0.066 (4)
H2A	0.4038	0.0519	0.3400	0.079*
C3	0.3505 (13)	0.1739 (8)	0.3527 (9)	0.064 (4)
H3A	0.3989	0.2014	0.3045	0.076*
C4	0.2128 (11)	0.1516 (8)	0.4794 (8)	0.050 (3)
H4A	0.1545	0.1609	0.5315	0.060*
C5	0.2341 (14)	0.3012 (8)	0.4287 (9)	0.068 (4)
H5A	0.1515	0.3121	0.4704	0.081*
H5B	0.1983	0.3228	0.3646	0.081*
C6	0.3818 (15)	0.3485 (8)	0.4682 (9)	0.074 (4)
H6A	0.4681	0.3349	0.4304	0.089*
H6B	0.3630	0.4087	0.4637	0.089*
C7	0.4240 (18)	0.3240 (9)	0.5717 (11)	0.096 (5)
H7A	0.4352	0.2634	0.5770	0.115*
H7B	0.3414	0.3416	0.6106	0.115*
C8	0.5739 (14)	0.4410 (8)	0.6537 (8)	0.057 (3)
H8A	0.4833	0.4729	0.6583	0.068*
C9	0.7154 (16)	0.4612 (8)	0.6906 (9)	0.067 (4)
H9A	0.7468	0.5103	0.7240	0.080*
C10	0.7192 (13)	0.3354 (8)	0.6172 (8)	0.055 (3)
H10A	0.7515	0.2842	0.5934	0.065*
C11	0.9894 (14)	0.3870 (10)	0.7007 (12)	0.107 (6)
H11A	1.0261	0.4384	0.7320	0.160*
H11B	1.0442	0.3778	0.6444	0.160*
H11C	1.0094	0.3408	0.7450	0.160*
Cd1	0.77770 (8)	0.15445 (5)	0.80145 (6)	0.0423 (2)
Br1	0.79089 (15)	0.29343 (8)	0.89683 (10)	0.0652 (4)
Br2	0.50899 (14)	0.13451 (8)	0.69780 (10)	0.0643 (4)
Br3	1.00029 (15)	0.14239 (11)	0.69122 (10)	0.0832 (5)
Br4	0.8109 (2)	0.04053 (11)	0.92709 (13)	0.1013 (6)

	U11	U22	U33	U12	U13	U23
N1	0.048 (6)	0.046 (6)	0.043 (5)	−0.003 (5)	0.011 (4)	−0.003 (4)
N2	0.040 (6)	0.056 (6)	0.061 (6)	0.011 (5)	0.004 (5)	−0.009 (5)
N3	0.046 (6)	0.034 (6)	0.092 (8)	−0.013 (4)	−0.031 (5)	0.002 (5)
N4	0.044 (5)	0.057 (6)	0.042 (5)	−0.002 (5)	0.010 (4)	0.021 (5)
C1	0.097 (11)	0.091 (11)	0.094 (11)	−0.056 (9)	0.004 (9)	0.006 (10)
C2	0.062 (9)	0.070 (9)	0.070 (9)	−0.008 (7)	0.029 (7)	−0.016 (7)
C3	0.054 (8)	0.077 (10)	0.063 (8)	−0.019 (7)	0.020 (6)	−0.018 (7)
C4	0.031 (6)	0.081 (9)	0.037 (6)	0.006 (6)	0.005 (5)	−0.009 (7)
C5	0.064 (9)	0.077 (10)	0.055 (8)	−0.001 (7)	−0.027 (6)	0.004 (7)
C6	0.094 (10)	0.073 (9)	0.056 (8)	0.005 (8)	0.009 (7)	0.000 (8)
C7	0.122 (14)	0.065 (10)	0.099 (12)	−0.021 (9)	0.005 (10)	−0.013 (8)
C8	0.054 (8)	0.062 (9)	0.052 (7)	0.002 (6)	−0.001 (6)	−0.003 (6)
C9	0.103 (11)	0.043 (7)	0.052 (7)	0.010 (8)	0.004 (7)	−0.009 (6)
C10	0.045 (7)	0.061 (8)	0.057 (7)	−0.006 (6)	0.001 (6)	0.015 (6)
C11	0.053 (9)	0.080 (11)	0.183 (18)	−0.017 (8)	−0.009 (10)	0.034 (11)
Cd1	0.0313 (4)	0.0491 (5)	0.0475 (5)	−0.0006 (4)	0.0080 (3)	−0.0051 (4)
Br1	0.0724 (9)	0.0536 (8)	0.0706 (9)	−0.0055 (6)	0.0119 (7)	−0.0081 (6)
Br2	0.0457 (7)	0.0684 (9)	0.0760 (9)	−0.0047 (6)	−0.0061 (6)	−0.0025 (7)
Br3	0.0583 (8)	0.1260 (14)	0.0684 (9)	0.0112 (9)	0.0214 (7)	−0.0020 (9)
Br4	0.1088 (13)	0.0956 (12)	0.1011 (12)	0.0178 (10)	0.0180 (10)	0.0049 (10)

N1—C4	1.342 (13)	C5—C6	1.514 (16)
N1—C1	1.400 (15)	C5—H5A	0.9700
N1—C2	1.412 (13)	C5—H5B	0.9700
N2—C4	1.297 (13)	C6—C7	1.490 (17)
N2—C3	1.423 (14)	C6—H6A	0.9700
N2—C5	1.475 (15)	C6—H6B	0.9700
N3—C10	1.286 (13)	C7—H7A	0.9700
N3—C8	1.341 (14)	C7—H7B	0.9700
N3—C7	1.519 (15)	C8—C9	1.297 (15)
N4—C10	1.362 (13)	C8—H8A	0.9300
N4—C9	1.391 (13)	C9—H9A	0.9300
N4—C11	1.545 (14)	C10—H10A	0.9300
C1—H1A	0.9600	C11—H11A	0.9600
C1—H1B	0.9600	C11—H11B	0.9600
C1—H1C	0.9600	C11—H11C	0.9600
C2—C3	1.321 (17)	Cd1—Br4	2.5036 (19)
C2—H2A	0.9300	Cd1—Br3	2.5608 (16)
C3—H3A	0.9300	Cd1—Br1	2.5673 (15)
C4—H4A	0.9300	Cd1—Br2	2.5858 (16)
C4—N1—C1	126.2 (10)	C7—C6—C5	108.9 (11)
C4—N1—C2	105.5 (9)	C7—C6—H6A	109.9
C1—N1—C2	128.3 (11)	C5—C6—H6A	109.9
C4—N2—C3	110.5 (10)	C7—C6—H6B	109.9
C4—N2—C5	127.7 (11)	C5—C6—H6B	109.9
C3—N2—C5	121.5 (11)	H6A—C6—H6B	108.3
C10—N3—C8	111.6 (9)	C6—C7—N3	108.2 (11)
C10—N3—C7	128.6 (11)	C6—C7—H7A	110.0
C8—N3—C7	118.6 (11)	N3—C7—H7A	110.0
C10—N4—C9	109.1 (10)	C6—C7—H7B	110.0
C10—N4—C11	126.2 (11)	N3—C7—H7B	110.0
C9—N4—C11	124.7 (12)	H7A—C7—H7B	108.4
N1—C1—H1A	109.5	C9—C8—N3	109.2 (11)
N1—C1—H1B	109.5	C9—C8—H8A	125.4
H1A—C1—H1B	109.5	N3—C8—H8A	125.4
N1—C1—H1C	109.5	C8—C9—N4	105.0 (11)
H1A—C1—H1C	109.5	C8—C9—H9A	127.5
H1B—C1—H1C	109.5	N4—C9—H9A	127.5
C3—C2—N1	110.6 (11)	N3—C10—N4	105.0 (10)
C3—C2—H2A	124.7	N3—C10—H10A	127.5
N1—C2—H2A	124.7	N4—C10—H10A	127.5
C2—C3—N2	103.7 (11)	N4—C11—H11A	109.5
C2—C3—H3A	128.1	N4—C11—H11B	109.5
N2—C3—H3A	128.1	H11A—C11—H11B	109.5
N2—C4—N1	109.6 (9)	N4—C11—H11C	109.5
N2—C4—H4A	125.2	H11A—C11—H11C	109.5
N1—C4—H4A	125.2	H11B—C11—H11C	109.5
N2—C5—C6	113.6 (10)	Br4—Cd1—Br3	108.87 (6)
N2—C5—H5A	108.9	Br4—Cd1—Br1	105.57 (6)
C6—C5—H5A	108.9	Br3—Cd1—Br1	112.06 (6)
N2—C5—H5B	108.9	Br4—Cd1—Br2	108.95 (6)
C6—C5—H5B	108.9	Br3—Cd1—Br2	109.04 (6)
H5A—C5—H5B	107.7	Br1—Cd1—Br2	112.23 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Br2	0.97	2.67	3.515 (15)	145.
C1—H1C···Br3i	0.96	2.93	3.819 (13)	155.
C4—H4A···Br3ii	0.93	2.70	3.606 (11)	164.
C5—H5B···Br3iii	0.97	2.84	3.765 (11)	161.
C8—H8A···Br4iv	0.93	2.86	3.699 (12)	151.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Br2	0.97	2.67	3.515 (15)	145
C1—H1C⋯Br3i	0.96	2.93	3.819 (13)	155
C4—H4A⋯Br3ii	0.93	2.70	3.606 (11)	164
C5—H5B⋯Br3iii	0.97	2.84	3.765 (11)	161
C8—H8A⋯Br4iv	0.93	2.86	3.699 (12)	151

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .