Poly[1-ethyl-3-methyl-imidazolium [tri-μ-chlorido-chromate(II)]].

The title compound, {(C(6)H(11)N(2))[CrCl(3)]}(n), was generated via mixing of the ionic liquid 1-ethyl-3-methyl-imidazolium chloride with CrCl(2) in ethanol. Crystals were obtained by a diffusion method. In the crystal structure, the anion forms one-dimensional chains of chloride-bridged Jahn-Teller distorted chromium(II) centers extending along the [100] direction. The imidazolium cations are positioned between these chains.

Related literature

For reference to this compound as a possible catalyst for the conversion of glucose to 5-hydroxy­methyl­furfural (HMF), see: Zhao et al. (2007 ▶). For the synthesis of the ammonium and tetra­methyl­ammonium analogs [NR 4][CrCl3] (R = H, CH3), see Hardt & Streit (1970 ▶). For the crystal structures of [M][CrCl3], see: Bellitto et al. (1984 ▶) [M = N(CH3)4]; McPherson et al. (1972 ▶) (M = Cs); Crama et al. (1978 ▶) (M = Rb, Cs); Crama et al. (1979 ▶) (M = Rb); Crama & Zandbergen (1981 ▶) (M = Cs).

Experimental

Crystal data

(C6H11N2)[CrCl3]

M = 269.52

Monoclinic,

a = 6.66150 (10) Å

b = 16.4317 (4) Å

c = 9.5258 (2) Å

β = 95.6881 (14)°

V = 1037.56 (4) Å3

Z = 4

Mo Kα radiation

μ = 1.82 mm−1

T = 150 (1) K

0.25 × 0.20 × 0.15 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan [DENZO-SMN (Otwinowski & Minor, 1997 ▶) with scaling algorithm from Fox & Holmes (1966 ▶)] T min = 0.659, T max = 0.772

4056 measured reflections

2384 independent reflections

2082 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.026

wR(F 2) = 0.064

S = 1.08

2384 reflections

154 parameters

All H-atom parameters refined

Δρmax = 0.42 e Å−3

Δρmin = −0.48 e Å−3

Data collection: COLLECT (Nonius, 1999 ▶); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ▶); data reduction: DENZO-SMN; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: WinGX (Farrugia, 1999 ▶); software used to prepare material for publication: CrystalMaker (Palmer, 2005 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002281/si2146sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002281/si2146Isup2.hkl

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

(C6H11N2)[CrCl3]	F(000) = 544
Mr = 269.52	Dx = 1.725 Mg m−3
Monoclinic, P21/a	Mo Kα radiation, λ = 0.71073 Å
a = 6.6615 (1) Å	Cell parameters from 8584 reflections
b = 16.4317 (4) Å	θ = 1.0–27.5°
c = 9.5258 (2) Å	µ = 1.82 mm−1
β = 95.6881 (14)°	T = 150 K
V = 1037.56 (4) Å3	Prism, yellow
Z = 4	0.25 × 0.20 × 0.15 mm

Nonius KappaCCD diffractometer	2384 independent reflections
Radiation source: fine-focus sealed tube	2082 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan [DENZO-SMN (Otwinowski & Minor, 1997) with scaling algorithm from Fox & Holmes (1966)]	h = −8→8
Tmin = 0.659, Tmax = 0.772	k = −20→21
4056 measured reflections	l = −12→12

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)] = 0.026	All H-atom parameters refined
wR(F2) = 0.064	w = 1/[σ2(Fo2) + (0.0236P)2 + 0.6211P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
2384 reflections	Δρmax = 0.42 e Å−3
154 parameters	Δρmin = −0.48 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0064 (9)

Experimental. The program DENZO-SMN (Otwinowski & Minor, 1997) uses a scaling algorithm (Fox & Holmes, 1966) which effectively corrects for absorption effects. High redundancy data were used in the scaling program hence the 'multi-scan' code word was used. No transmission coefficients are available from the program (only scale factors for each frame). The scale factors in the experimental table are calculated from the 'size' command in the SHELXL97 input file.

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
Cr1	0.30848 (4)	0.251150 (16)	0.79201 (3)	0.01432 (10)
Cl1	0.09238 (6)	0.18418 (3)	0.61278 (4)	0.01959 (12)
Cl2	0.52336 (6)	0.31399 (3)	0.97636 (4)	0.01856 (12)
Cl3	0.55581 (5)	0.14110 (3)	0.79810 (4)	0.01695 (12)
N1	0.7020 (2)	0.05812 (10)	0.24223 (15)	0.0209 (3)
N2	0.4931 (2)	0.14965 (9)	0.30051 (15)	0.0191 (3)
C1	0.5869 (3)	0.11968 (12)	0.19414 (18)	0.0198 (4)
C2	0.6805 (3)	0.04791 (13)	0.3837 (2)	0.0301 (4)
C3	0.5517 (3)	0.10515 (13)	0.4202 (2)	0.0281 (4)
C4	0.3515 (3)	0.21791 (13)	0.2924 (2)	0.0243 (4)
C5	0.8379 (3)	0.01037 (13)	0.1611 (2)	0.0269 (4)
C6	1.0520 (3)	0.01492 (15)	0.2275 (3)	0.0339 (5)
H1	0.574 (3)	0.1415 (13)	0.104 (2)	0.022 (5)*
H2	0.748 (4)	0.0075 (16)	0.435 (3)	0.043 (7)*
H3	0.508 (4)	0.1180 (16)	0.506 (3)	0.044 (7)*
H4A	0.350 (5)	0.2419 (19)	0.206 (4)	0.071 (10)*
H4B	0.236 (5)	0.1996 (19)	0.309 (3)	0.068 (9)*
H4C	0.384 (4)	0.2545 (18)	0.356 (3)	0.059 (9)*
H5A	0.829 (4)	0.0344 (15)	0.067 (3)	0.042 (7)*
H5B	0.787 (4)	−0.0452 (16)	0.156 (2)	0.040 (6)*
H6A	1.142 (4)	−0.0168 (17)	0.176 (3)	0.047 (7)*
H6B	1.061 (3)	−0.0057 (16)	0.319 (3)	0.040 (7)*
H6C	1.099 (4)	0.0705 (19)	0.240 (3)	0.059 (8)*

	U11	U22	U33	U12	U13	U23
Cr1	0.01154 (15)	0.01684 (18)	0.01412 (15)	0.00097 (10)	−0.00098 (10)	−0.00138 (10)
Cl1	0.0171 (2)	0.0254 (3)	0.0157 (2)	−0.00134 (16)	−0.00144 (15)	−0.00269 (16)
Cl2	0.0179 (2)	0.0211 (2)	0.0160 (2)	−0.00030 (15)	−0.00131 (15)	−0.00306 (16)
Cl3	0.0136 (2)	0.0164 (2)	0.0207 (2)	−0.00014 (14)	0.00140 (15)	−0.00127 (15)
N1	0.0225 (7)	0.0204 (8)	0.0203 (7)	−0.0013 (6)	0.0042 (6)	0.0004 (6)
N2	0.0186 (7)	0.0226 (8)	0.0161 (7)	−0.0017 (6)	0.0011 (5)	−0.0013 (6)
C1	0.0210 (8)	0.0225 (9)	0.0161 (8)	−0.0027 (7)	0.0021 (7)	−0.0006 (7)
C2	0.0343 (10)	0.0329 (12)	0.0234 (9)	0.0053 (9)	0.0043 (8)	0.0090 (9)
C3	0.0303 (10)	0.0373 (12)	0.0172 (9)	0.0022 (9)	0.0043 (7)	0.0039 (8)
C4	0.0195 (9)	0.0278 (11)	0.0256 (10)	0.0013 (8)	0.0027 (7)	−0.0044 (9)
C5	0.0284 (10)	0.0215 (10)	0.0321 (10)	−0.0001 (8)	0.0087 (8)	−0.0030 (8)
C6	0.0277 (11)	0.0314 (13)	0.0434 (13)	0.0049 (9)	0.0072 (9)	0.0024 (10)

Cr1—Cl2	2.3876 (5)	C2—H2	0.91 (3)
Cr1—Cl1	2.3898 (5)	C3—H3	0.91 (3)
Cr1—Cl3	2.4431 (5)	C4—H4A	0.91 (3)
Cr1—Cl3i	2.4476 (5)	C4—H4B	0.86 (3)
N1—C1	1.323 (2)	C4—H4C	0.86 (3)
N1—C2	1.380 (2)	C5—C6	1.503 (3)
N1—C5	1.473 (2)	C5—H5A	0.97 (2)
N2—C1	1.336 (2)	C5—H5B	0.97 (3)
N2—C3	1.378 (2)	C6—H6A	0.96 (3)
N2—C4	1.463 (3)	C6—H6B	0.93 (3)
C1—H1	0.93 (2)	C6—H6C	0.97 (3)
C2—C3	1.342 (3)
Cl2—Cr1—Cl1	177.976 (19)	C2—C3—H3	131.2 (17)
Cl2—Cr1—Cl3	87.073 (15)	N2—C3—H3	121.7 (17)
Cl1—Cr1—Cl3	91.904 (16)	N2—C4—H4A	109 (2)
Cl2—Cr1—Cl3i	91.906 (16)	N2—C4—H4B	108 (2)
Cl1—Cr1—Cl3i	89.027 (15)	H4A—C4—H4B	113 (3)
Cl3—Cr1—Cl3i	176.95 (2)	N2—C4—H4C	112 (2)
Cr1—Cl3—Cr1ii	85.856 (13)	H4A—C4—H4C	108 (3)
C1—N1—C2	108.55 (16)	H4B—C4—H4C	106 (3)
C1—N1—C5	126.20 (16)	N1—C5—C6	111.08 (17)
C2—N1—C5	125.20 (17)	N1—C5—H5A	106.3 (14)
C1—N2—C3	108.45 (16)	C6—C5—H5A	109.7 (14)
C1—N2—C4	126.18 (16)	N1—C5—H5B	107.4 (14)
C3—N2—C4	125.37 (15)	C6—C5—H5B	112.2 (14)
N1—C1—N2	108.52 (15)	H5A—C5—H5B	110 (2)
N1—C1—H1	127.8 (13)	C5—C6—H6A	111.9 (15)
N2—C1—H1	123.6 (13)	C5—C6—H6B	110.2 (15)
C3—C2—N1	107.38 (18)	H6A—C6—H6B	107 (2)
C3—C2—H2	131.7 (16)	C5—C6—H6C	112.4 (17)
N1—C2—H2	121.0 (16)	H6A—C6—H6C	111 (2)
C2—C3—N2	107.08 (16)	H6B—C6—H6C	104 (2)
Cl2—Cr1—Cl3—Cr1ii	−48.298 (16)	C5—N1—C2—C3	176.88 (18)
Cl1—Cr1—Cl3—Cr1ii	133.450 (13)	N1—C2—C3—N2	0.6 (2)
C2—N1—C1—N2	0.4 (2)	C1—N2—C3—C2	−0.4 (2)
C5—N1—C1—N2	−177.10 (16)	C4—N2—C3—C2	179.39 (18)
C3—N2—C1—N1	0.0 (2)	C1—N1—C5—C6	121.0 (2)
C4—N2—C1—N1	−179.80 (17)	C2—N1—C5—C6	−56.1 (3)
C1—N1—C2—C3	−0.7 (2)

Cr1—Cl2	2.3876 (5)
Cr1—Cl1	2.3898 (5)
Cr1—Cl3	2.4431 (5)
Cr1—Cl3i	2.4476 (5)

Cl2—Cr1—Cl1	177.976 (19)
Cl2—Cr1—Cl3	87.073 (15)
Cl1—Cr1—Cl3	91.904 (16)
Cl2—Cr1—Cl3i	91.906 (16)
Cl1—Cr1—Cl3i	89.027 (15)
Cl3—Cr1—Cl3i	176.95 (2)
Cr1—Cl3—Cr1ii	85.856 (13)

Symmetry codes: (i) ; (ii) .