catena-Poly[1-butyl-3-methyl­imidazolium [[dichlorido(methanol-κO)(propan-2-ol-κO)lanthanate(III)]-di-μ-chlorido]]

Han, Y.; Dai, F.; Sykes, A.G.; May, P.S.; Berry, M.T.; Meng, Q.; Lin, C.

doi:10.1107/S160053681200517X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages m292-m293

doi:10.1107/S160053681200517X

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catena-Poly[1-butyl-3-methylimidazolium [[dichlorido(methanol-κO)(propan-2-ol-κO)lanthanate(III)]-di-μ-chlorido]]

Yulun Han,^a Fengrong Dai,^a Andrew G. Sykes,^a P. Stanley May,^a Mary T. Berry,^a Qingguo Meng ^a ^* and Cuikun Lin ^a ^*

^aDepartment of Chemistry, University of South Dakota, 414E Clark, CL115, Vermillion, SD 57069, USA
^*Correspondence e-mail: qingguo.meng@usd.edu, cuikun.lin@usd.edu

(Received 13 January 2012; accepted 6 February 2012; online 17 February 2012)

The title compound, (C₈H₁₅N₂)[LaCl₄(CH₃OH)(C₃H₇OH)], consists of one 1-butyl-3-methylimidazolium (BMI⁺) cation and one hexahedral tetrachlorido(methanol)(propan-2-ol)lanthanate anion. The La^III ion is eight-coordinate, with the La^III ion bridged by a pair of Cl atoms, so forming chains propagating along the a-axis direction. Each La^III ion is further coordinated by two isolated Cl atoms, one methanol and one propan-2-ol molecule. The coordinated methanol and propan-2-ol molecules of the anion form O—H⋯Cl hydrogen bonds with the Cl atoms of inversion-related anions. The BMI⁺ cation froms C—H⋯Cl hydrogen bonds with the Cl atoms of the anion. The anions are located in the C faces of the triclinic unit cell, with an inversion center in the middle of the La₂Cl₂ ring of the polymeric chain.

Related literature

For related crystal structures, see: Binnemans (2007 ); Pellens et al. (2008 ); Matsumoto et al. (2002 ). For the synthesis of the title compound, see: Burrell et al. (2007 ). For the optical properties of lanthanides in ionic liquids, see: Brandner et al. (2011 ); Samikkanu et al. (2007 ).

Experimental

Crystal data

(C₈H₁₅N₂)[LaCl₄(CH₄O)(C₃H₈O)]
M_r = 512.07
Triclinic, $[P \overline 1]$
a = 9.5035 (6) Å
b = 10.7413 (6) Å
c = 11.8625 (7) Å
α = 114.009 (1)°
β = 109.735 (1)°
γ = 92.857 (1)°
V = 1016.20 (10) Å³
Z = 2
Mo Kα radiation
μ = 2.63 mm⁻¹
T = 100 K
0.30 × 0.15 × 0.05 mm

Data collection

Bruker APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.506, T_max = 0.880
11178 measured reflections
4155 independent reflections
3780 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.022
wR(F²) = 0.049
S = 1.04
4155 reflections
198 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1D⋯Cl2ⁱ	0.79 (4)	2.42 (4)	3.206 (2)	171 (4)
O2—H2B⋯Cl1ⁱⁱ	0.75 (4)	2.39 (4)	3.122 (2)	166 (4)
C5—H5A⋯Cl3ⁱⁱⁱ	0.93	2.65	3.458 (3)	145
C8—H8A⋯Cl3ⁱⁱⁱ	0.96	2.67	3.565 (3)	156
Symmetry codes: (i) -x+2, -y+1, -z; (ii) -x+1, -y+1, -z; (iii) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681200517X/su2369sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681200517X/su2369Isup2.hkl

checkCIF report

Comment top

Ionic liquids (ILs) have received considerable attention due to their extraordinary properties as solvents (Binnemans, 2007). They have been proposed as excellent alternatives to conventional solvents for luminescent lanthanide complexes. Compared with aqueous or organic solvents, ILs have the advantages of potentially excluding quenching oscillators, providing greater luminescence quantum yields (Brandner et al., 2011; Samikkanu et al., 2007). Some analogous structures to the title compound, tris(1-ethyl-3-methylimidazolium)hexabromidoeuropate(III) (Pellens et al., 2008) and tris(1-ethyl-3-methylimidazolium)hexachloridolanthanate(III) (Matsumoto et al., 2002) have been reported.

The title compound, in contrast to these examples, includes coordinated alcohol molecules and crystallized after mixing lanthanum chloride in 1-butyl-3-methylimidazolium chloride (BMICl) with a mixture of methanol and propan-2-ol (Fig. 1). The bond lengths between La and the two non-bridging Cl atoms are 2.8232 (5) Å and 2.838 (1) Å, respectively. The La to bridging Cl distances are in the range of 2.8884 (6) Å and 3.0021 (8) Å. All the Cl atoms, except Cl4, exhibit short contacts to neighboring H atoms on the imidazolium rings or on alcohol molecules ranging from 2.653 Å to 2.909 Å.

In the crystal, H atoms in the imidazolium cations, such as H5A and H8A, form hydrogen bonds with chlorine Cl3 (Fig. 2 and Table 1). The two H atoms in methanol (H2B) and propan-2-ol (H1D) form hydrogen bonds with atoms Cl2 and Cl1, respectively (Table 1). The [LaCl₄(CH₃OH)(i-C₃H₉OH)]^- anions are centered in the C faces of the triclinic unit cell, with an inversion center in the middle of La₂Cl₂ ring, as shown in Fig. 3. The BMI⁺ cation is on an inversion center, at position (1/2, 1/2, 1/2) in the unit cell.

Related literature top

For related crystal structures, see: Binnemans (2007); Pellens et al. (2008); Matsumoto et al. (2002). For the synthesis of the title compound, see: Burrell et al. (2007). For the optical properties of lanthanides in ionic liquids, see: Brandner et al. (2011); Samikkanu et al. (2007).

Experimental top

1-butyl-3-methylimidazolium chloride (BMICl) was synthesized following a method reported by Burrell et al. (2007). Lanthanum chloride heptahydrate (0.708 g, 1.906 mmol) was mixed with BMICl (1.000 g, 5.725 mmol) in a small vial in a glove box. Equal amount of methanol and propan-2-ol were added carefully until the total dissolution of the mixture. The vial was sealed and a colourless crystal appeared after cooling at 258 K for three weeks.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the asymmetric unit of the title compound, with the numbering scheme and displacement ellipsoids drawn at the 50% probability level. H atoms have been omitted for clarify.
	Fig. 2. A view of the molecular structure of the title compound, with the dashed lines denoting the hydrogen bonding.
	Fig. 3. Crystal packing of the title compound viewed along the a axis. The [LaCl₄(CH₃OH)(i-C₃H₉OH)]^- anions are located about the inversion centers in the C faces of the triclinic unit cell.

catena-Poly[1-butyl-3-methylimidazolium [[dichlorido(methanol- κO)(propan-2-ol-κO)lanthanate(III)]-di-µ-chlorido]] top

Crystal data top

(C₈H₁₅N₂)[LaCl₄(CH₄O)(C₃H₈O)]	Z = 2
M_r = 512.07	F(000) = 508
Triclinic, P1	D_x = 1.674 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5035 (6) Å	Cell parameters from 8208 reflections
b = 10.7413 (6) Å	θ = 2.3–26.4°
c = 11.8625 (7) Å	µ = 2.63 mm⁻¹
α = 114.009 (1)°	T = 100 K
β = 109.735 (1)°	Block, colourless
γ = 92.857 (1)°	0.30 × 0.15 × 0.05 mm
V = 1016.20 (10) Å³

Data collection top

Bruker APEXII CCD area-detector diffractometer	4155 independent reflections
Radiation source: fine-focus sealed tube	3780 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.029
ϕ and ω scans	θ_max = 26.4°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −11→11
T_min = 0.506, T_max = 0.880	k = −13→13
11178 measured reflections	l = −14→14

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)] = 0.022	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0193P)² + 0.4077P] where P = (F_o² + 2F_c²)/3
4155 reflections	(Δ/σ)_max = 0.001
198 parameters	Δρ_max = 0.71 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

(C₈H₁₅N₂)[LaCl₄(CH₄O)(C₃H₈O)]	γ = 92.857 (1)°
M_r = 512.07	V = 1016.20 (10) Å³
Triclinic, P1	Z = 2
a = 9.5035 (6) Å	Mo Kα radiation
b = 10.7413 (6) Å	µ = 2.63 mm⁻¹
c = 11.8625 (7) Å	T = 100 K
α = 114.009 (1)°	0.30 × 0.15 × 0.05 mm
β = 109.735 (1)°

Data collection top

Bruker APEXII CCD area-detector diffractometer	4155 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3780 reflections with I > 2σ(I)
T_min = 0.506, T_max = 0.880	R_int = 0.029
11178 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.022	0 restraints
wR(F²) = 0.049	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.71 e Å⁻³
4155 reflections	Δρ_min = −0.59 e Å⁻³
198 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
La1	0.739307 (15)	0.491237 (15)	−0.023339 (14)	0.00964 (5)
Cl1	0.54404 (7)	0.24123 (7)	−0.24214 (6)	0.01713 (14)
Cl2	0.77665 (7)	0.64602 (7)	−0.16020 (7)	0.01686 (14)
Cl3	1.05144 (7)	0.63430 (7)	0.15869 (6)	0.01356 (13)
Cl4	0.56003 (7)	0.42798 (7)	0.11059 (6)	0.01393 (13)
O1	0.8605 (2)	0.3297 (2)	0.0650 (2)	0.0176 (4)
H1D	0.951 (4)	0.344 (4)	0.096 (4)	0.042 (11)*
O2	0.7406 (2)	0.7145 (2)	0.16709 (19)	0.0169 (4)
H2B	0.668 (4)	0.710 (4)	0.180 (4)	0.040 (12)*
N1	0.6581 (2)	0.1728 (2)	0.4667 (2)	0.0145 (5)
N2	0.6359 (2)	0.3591 (2)	0.4388 (2)	0.0148 (5)
C1	0.7807 (3)	0.8505 (3)	0.1784 (3)	0.0253 (7)
H1A	0.7734	0.9196	0.2577	0.038*
H1B	0.7118	0.8565	0.1010	0.038*
H1C	0.8837	0.8666	0.1841	0.038*
C2	0.7981 (3)	0.1900 (3)	0.0376 (3)	0.0218 (6)
H2A	0.6864	0.1766	0.0048	0.026*
C3	0.8374 (3)	0.0814 (3)	−0.0713 (3)	0.0297 (7)
H3A	0.7993	0.0941	−0.1509	0.045*
H3B	0.7911	−0.0104	−0.0907	0.045*
H3C	0.9465	0.0918	−0.0409	0.045*
C4	0.8534 (4)	0.1779 (4)	0.1663 (3)	0.0335 (8)
H4A	0.8255	0.2488	0.2310	0.050*
H4B	0.9628	0.1897	0.2001	0.050*
H4C	0.8073	0.0875	0.1502	0.050*
C5	0.6982 (3)	0.3114 (3)	0.5278 (3)	0.0152 (6)
H5A	0.7599	0.3662	0.6180	0.018*
C6	0.5659 (3)	0.1306 (3)	0.3339 (3)	0.0188 (6)
H6A	0.5214	0.0389	0.2686	0.023*
C7	0.5522 (3)	0.2461 (3)	0.3163 (3)	0.0195 (6)
H7A	0.4967	0.2492	0.2365	0.023*
C8	0.7080 (3)	0.0804 (3)	0.5284 (3)	0.0168 (6)
H8A	0.7713	0.1356	0.6219	0.025*
H8B	0.7654	0.0220	0.4847	0.025*
H8C	0.6199	0.0232	0.5191	0.025*
C9	0.6552 (3)	0.5071 (3)	0.4667 (3)	0.0167 (6)
H9A	0.6495	0.5616	0.5526	0.020*
H9B	0.5712	0.5167	0.3986	0.020*
C10	0.8046 (3)	0.5662 (3)	0.4693 (3)	0.0175 (6)
H10A	0.8113	0.5136	0.3833	0.021*
H10B	0.8899	0.5585	0.5378	0.021*
C11	0.8133 (3)	0.7191 (3)	0.4988 (3)	0.0199 (6)
H11A	0.8119	0.7717	0.5869	0.024*
H11B	0.7238	0.7264	0.4335	0.024*
C12	0.9580 (3)	0.7831 (3)	0.4944 (3)	0.0250 (7)
H12A	0.9588	0.8790	0.5135	0.038*
H12B	0.9588	0.7325	0.4068	0.038*
H12C	1.0469	0.7778	0.5601	0.038*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
La1	0.00730 (8)	0.00983 (8)	0.01066 (8)	0.00150 (5)	0.00309 (6)	0.00398 (6)
Cl1	0.0115 (3)	0.0139 (3)	0.0183 (3)	0.0012 (2)	0.0051 (3)	0.0010 (3)
Cl2	0.0131 (3)	0.0205 (4)	0.0221 (3)	0.0054 (3)	0.0073 (3)	0.0138 (3)
Cl3	0.0089 (3)	0.0143 (3)	0.0129 (3)	0.0018 (2)	0.0032 (2)	0.0029 (3)
Cl4	0.0113 (3)	0.0179 (3)	0.0158 (3)	0.0046 (2)	0.0060 (2)	0.0099 (3)
O1	0.0107 (10)	0.0165 (10)	0.0292 (11)	0.0036 (8)	0.0068 (9)	0.0143 (9)
O2	0.0120 (10)	0.0131 (10)	0.0206 (11)	−0.0001 (8)	0.0072 (8)	0.0027 (8)
N1	0.0128 (11)	0.0147 (12)	0.0153 (11)	0.0024 (9)	0.0057 (9)	0.0061 (10)
N2	0.0118 (11)	0.0168 (12)	0.0173 (12)	0.0046 (9)	0.0077 (9)	0.0073 (10)
C1	0.0278 (16)	0.0136 (15)	0.0324 (18)	0.0036 (12)	0.0152 (14)	0.0059 (13)
C2	0.0188 (14)	0.0170 (15)	0.0346 (17)	0.0055 (12)	0.0112 (13)	0.0156 (14)
C3	0.0246 (16)	0.0244 (17)	0.0350 (19)	0.0063 (13)	0.0079 (14)	0.0117 (15)
C4	0.041 (2)	0.0298 (19)	0.038 (2)	0.0069 (15)	0.0174 (16)	0.0215 (16)
C5	0.0124 (13)	0.0172 (14)	0.0124 (13)	0.0032 (11)	0.0039 (10)	0.0042 (11)
C6	0.0169 (14)	0.0161 (15)	0.0153 (14)	0.0017 (11)	0.0034 (11)	0.0023 (12)
C7	0.0173 (14)	0.0205 (15)	0.0132 (14)	0.0036 (11)	0.0013 (11)	0.0045 (12)
C8	0.0179 (14)	0.0158 (14)	0.0165 (14)	0.0034 (11)	0.0080 (11)	0.0061 (12)
C9	0.0163 (14)	0.0162 (14)	0.0207 (15)	0.0066 (11)	0.0081 (11)	0.0102 (12)
C10	0.0136 (13)	0.0188 (15)	0.0173 (14)	0.0029 (11)	0.0052 (11)	0.0065 (12)
C11	0.0174 (14)	0.0189 (15)	0.0231 (15)	0.0046 (11)	0.0066 (12)	0.0101 (13)
C12	0.0231 (15)	0.0249 (17)	0.0271 (17)	0.0023 (13)	0.0089 (13)	0.0128 (14)

Geometric parameters (Å, º) top

La1—O1	2.5102 (19)	C3—H3A	0.9600
La1—O2	2.5348 (19)	C3—H3B	0.9600
La1—Cl1	2.8232 (6)	C3—H3C	0.9600
La1—Cl2	2.8378 (7)	C4—H4A	0.9600
La1—Cl3	2.8884 (6)	C4—H4B	0.9600
La1—Cl4	2.9119 (6)	C4—H4C	0.9600
La1—Cl4ⁱ	2.9841 (6)	C5—H5A	0.9300
La1—Cl3ⁱⁱ	3.0021 (6)	C6—C7	1.346 (4)
Cl3—La1ⁱⁱ	3.0021 (6)	C6—H6A	0.9300
Cl4—La1ⁱ	2.9841 (6)	C7—H7A	0.9300
O1—C2	1.446 (3)	C8—H8A	0.9600
O1—H1D	0.79 (4)	C8—H8B	0.9600
O2—C1	1.431 (3)	C8—H8C	0.9600
O2—H2B	0.75 (4)	C9—C10	1.512 (4)
N1—C5	1.329 (3)	C9—H9A	0.9700
N1—C6	1.378 (3)	C9—H9B	0.9700
N1—C8	1.466 (3)	C10—C11	1.525 (4)
N2—C5	1.332 (3)	C10—H10A	0.9700
N2—C7	1.381 (3)	C10—H10B	0.9700
N2—C9	1.474 (3)	C11—C12	1.533 (4)
C1—H1A	0.9600	C11—H11A	0.9700
C1—H1B	0.9600	C11—H11B	0.9700
C1—H1C	0.9600	C12—H12A	0.9600
C2—C4	1.500 (4)	C12—H12B	0.9600
C2—C3	1.520 (4)	C12—H12C	0.9600
C2—H2A	0.9800

O1—La1—O2	110.49 (6)	C3—C2—H2A	107.9
O1—La1—Cl1	83.72 (5)	C2—C3—H3A	109.5
O2—La1—Cl1	142.48 (5)	C2—C3—H3B	109.5
O1—La1—Cl2	141.74 (5)	H3A—C3—H3B	109.5
O2—La1—Cl2	89.42 (5)	C2—C3—H3C	109.5
Cl1—La1—Cl2	100.30 (2)	H3A—C3—H3C	109.5
O1—La1—Cl3	72.67 (5)	H3B—C3—H3C	109.5
O2—La1—Cl3	70.43 (5)	C2—C4—H4A	109.5
Cl1—La1—Cl3	146.015 (18)	C2—C4—H4B	109.5
Cl2—La1—Cl3	84.745 (19)	H4A—C4—H4B	109.5
O1—La1—Cl4	72.72 (5)	C2—C4—H4C	109.5
O2—La1—Cl4	70.12 (5)	H4A—C4—H4C	109.5
Cl1—La1—Cl4	82.364 (19)	H4B—C4—H4C	109.5
Cl2—La1—Cl4	145.479 (18)	N1—C5—N2	109.0 (2)
Cl3—La1—Cl4	112.230 (18)	N1—C5—H5A	125.5
O1—La1—Cl4ⁱ	141.39 (5)	N2—C5—H5A	125.5
O2—La1—Cl4ⁱ	71.22 (5)	C7—C6—N1	107.5 (2)
Cl1—La1—Cl4ⁱ	76.418 (18)	C7—C6—H6A	126.3
Cl2—La1—Cl4ⁱ	75.142 (17)	N1—C6—H6A	126.3
Cl3—La1—Cl4ⁱ	136.524 (19)	C6—C7—N2	107.1 (2)
Cl4—La1—Cl4ⁱ	72.078 (19)	C6—C7—H7A	126.5
O1—La1—Cl3ⁱⁱ	70.16 (5)	N2—C7—H7A	126.5
O2—La1—Cl3ⁱⁱ	139.40 (5)	N1—C8—H8A	109.5
Cl1—La1—Cl3ⁱⁱ	77.752 (18)	N1—C8—H8B	109.5
Cl2—La1—Cl3ⁱⁱ	73.582 (18)	H8A—C8—H8B	109.5
Cl3—La1—Cl3ⁱⁱ	71.48 (2)	N1—C8—H8C	109.5
Cl4—La1—Cl3ⁱⁱ	139.352 (18)	H8A—C8—H8C	109.5
Cl4ⁱ—La1—Cl3ⁱⁱ	134.605 (17)	H8B—C8—H8C	109.5
La1—Cl3—La1ⁱⁱ	108.52 (2)	N2—C9—C10	113.7 (2)
La1—Cl4—La1ⁱ	107.922 (19)	N2—C9—H9A	108.8
C2—O1—La1	130.59 (16)	C10—C9—H9A	108.8
C2—O1—H1D	109 (3)	N2—C9—H9B	108.8
La1—O1—H1D	118 (3)	C10—C9—H9B	108.8
C1—O2—La1	123.48 (17)	H9A—C9—H9B	107.7
C1—O2—H2B	108 (3)	C9—C10—C11	109.5 (2)
La1—O2—H2B	112 (3)	C9—C10—H10A	109.8
C5—N1—C6	108.2 (2)	C11—C10—H10A	109.8
C5—N1—C8	125.9 (2)	C9—C10—H10B	109.8
C6—N1—C8	125.8 (2)	C11—C10—H10B	109.8
C5—N2—C7	108.2 (2)	H10A—C10—H10B	108.2
C5—N2—C9	125.7 (2)	C10—C11—C12	112.2 (2)
C7—N2—C9	126.1 (2)	C10—C11—H11A	109.2
O2—C1—H1A	109.5	C12—C11—H11A	109.2
O2—C1—H1B	109.5	C10—C11—H11B	109.2
H1A—C1—H1B	109.5	C12—C11—H11B	109.2
O2—C1—H1C	109.5	H11A—C11—H11B	107.9
H1A—C1—H1C	109.5	C11—C12—H12A	109.5
H1B—C1—H1C	109.5	C11—C12—H12B	109.5
O1—C2—C4	108.9 (2)	H12A—C12—H12B	109.5
O1—C2—C3	110.9 (2)	C11—C12—H12C	109.5
C4—C2—C3	113.2 (3)	H12A—C12—H12C	109.5
O1—C2—H2A	107.9	H12B—C12—H12C	109.5
C4—C2—H2A	107.9

O1—La1—Cl3—La1ⁱⁱ	74.31 (5)	Cl1—La1—O2—C1	−116.57 (19)
O2—La1—Cl3—La1ⁱⁱ	−165.68 (5)	Cl2—La1—O2—C1	−10.28 (19)
Cl1—La1—Cl3—La1ⁱⁱ	26.22 (4)	Cl3—La1—O2—C1	74.35 (19)
Cl2—La1—Cl3—La1ⁱⁱ	−74.42 (2)	Cl4—La1—O2—C1	−161.9 (2)
Cl4—La1—Cl3—La1ⁱⁱ	136.68 (2)	Cl4ⁱ—La1—O2—C1	−84.77 (19)
Cl4ⁱ—La1—Cl3—La1ⁱⁱ	−136.31 (2)	Cl3ⁱⁱ—La1—O2—C1	53.2 (2)
Cl3ⁱⁱ—La1—Cl3—La1ⁱⁱ	0.0	La1—O1—C2—C4	−139.1 (2)
O1—La1—Cl4—La1ⁱ	−163.89 (5)	La1—O1—C2—C3	95.8 (2)
O2—La1—Cl4—La1ⁱ	75.95 (5)	C6—N1—C5—N2	−0.4 (3)
Cl1—La1—Cl4—La1ⁱ	−78.13 (2)	C8—N1—C5—N2	177.5 (2)
Cl2—La1—Cl4—La1ⁱ	18.96 (4)	C7—N2—C5—N1	0.3 (3)
Cl3—La1—Cl4—La1ⁱ	133.77 (2)	C9—N2—C5—N1	−178.9 (2)
Cl4ⁱ—La1—Cl4—La1ⁱ	0.0	C5—N1—C6—C7	0.4 (3)
Cl3ⁱⁱ—La1—Cl4—La1ⁱ	−139.14 (2)	C8—N1—C6—C7	−177.5 (2)
O2—La1—O1—C2	119.5 (2)	N1—C6—C7—N2	−0.2 (3)
Cl1—La1—O1—C2	−24.7 (2)	C5—N2—C7—C6	0.0 (3)
Cl2—La1—O1—C2	−123.36 (19)	C9—N2—C7—C6	179.1 (2)
Cl3—La1—O1—C2	−179.9 (2)	C5—N2—C9—C10	80.0 (3)
Cl4—La1—O1—C2	59.3 (2)	C7—N2—C9—C10	−99.1 (3)
Cl4ⁱ—La1—O1—C2	34.2 (2)	N2—C9—C10—C11	−180.0 (2)
Cl3ⁱⁱ—La1—O1—C2	−103.9 (2)	C9—C10—C11—C12	−176.5 (2)
O1—La1—O2—C1	136.28 (19)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···Cl2ⁱⁱ	0.79 (4)	2.42 (4)	3.206 (2)	171 (4)
O2—H2B···Cl1ⁱ	0.75 (4)	2.39 (4)	3.122 (2)	166 (4)
C5—H5A···Cl3ⁱⁱⁱ	0.93	2.65	3.458 (3)	145
C8—H8A···Cl3ⁱⁱⁱ	0.96	2.67	3.565 (3)	156

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

Experimental details

Crystal data
Chemical formula	(C₈H₁₅N₂)[LaCl₄(CH₄O)(C₃H₈O)]
M_r	512.07
Crystal system, space group	Triclinic, P1
Temperature (K)	100
a, b, c (Å)	9.5035 (6), 10.7413 (6), 11.8625 (7)
α, β, γ (°)	114.009 (1), 109.735 (1), 92.857 (1)
V (Å³)	1016.20 (10)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.63
Crystal size (mm)	0.30 × 0.15 × 0.05

Data collection
Diffractometer	Bruker APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.506, 0.880
No. of measured, independent and observed [I > 2σ(I)] reflections	11178, 4155, 3780
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.022, 0.049, 1.04
No. of reflections	4155
No. of parameters	198
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.71, −0.59

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1D···Cl2ⁱ	0.79 (4)	2.42 (4)	3.206 (2)	171 (4)
O2—H2B···Cl1ⁱⁱ	0.75 (4)	2.39 (4)	3.122 (2)	166 (4)
C5—H5A···Cl3ⁱⁱⁱ	0.93	2.65	3.458 (3)	145.2
C8—H8A···Cl3ⁱⁱⁱ	0.96	2.67	3.565 (3)	156.0

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

Acknowledgements

The authors thank the National Science Foundation/EPSCoR (grant No. 0554609) and the State of South Dakota, Governor's Office of Economic Development, for financial support.

References

Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. CrossRef Web of Science IUCr Journals Google Scholar
Binnemans, K. (2007). Chem. Rev. 107, 2592–2614. Web of Science CrossRef PubMed CAS Google Scholar
Brandner, A., Kitahara, T., Beare, N., Lin, C. K., Berry, M. T. & May, P. S. (2011). Inorg. Chem. 50, 6509–6520. Web of Science CrossRef CAS PubMed Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Burrell, A. K., Del Sesto, R. E., Baker, S. N., McCleskey, T. M. & Baker, G. A. (2007). Green Chem. 9, 449–454. CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Matsumoto, K., Tsuda, T., Nohira, T., Hagiwara, R., Ito, Y. & Tamada, O. (2002). Acta Cryst. C58, m186–m187. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Pellens, M., Thijs, B., Van Hecke, K., Van Meervelt, L., Binnemans, K. & Nockemann, P. (2008). Acta Cryst. E64, m945. Web of Science CSD CrossRef IUCr Journals Google Scholar
Samikkanu, S., Mellem, K., Berry, M. T. & May, P. S. (2007). Inorg. Chem. 46, 7121–7128. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. Univeristy of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 3| March 2012| Pages m292-m293

doi:10.1107/S160053681200517X

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

catena-Poly[1-butyl-3-methyl­imidazolium [[di­chlorido(methanol-κO)(propan-2-ol-κO)lanthanate(III)]-di-μ-chlorido]]

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

catena-Poly[1-butyl-3-methylimidazolium [[dichlorido(methanol-κO)(propan-2-ol-κO)lanthanate(III)]-di-μ-chlorido]]