1,3-Bis(2,6-diisopropyl-phen-yl)-1H-imidazol-3-ium chloride dichloro-methane disolvate.

In the title compound, C(27)H(37)N(2) (+)·Cl(-)·2CH(2)Cl(2), the cation and the anion are each located on a crystallographic mirror plane. Both of the dichloro-methane solvent mol-ecules show a disorder across a mirror plane over two equally occupied positions. Additionally, one isopropyl group is also disordered. In the crystal, the cations are connected to the chloride ions via C-H⋯Cl hydrogen bonds.

Related literature

For the preparation of imidazolium salts, see: Arduengo et al. (1995 ▶, 1999 ▶); Hinter­mann (2007 ▶). For structures with the same cation but different anions, see: Stasch et al. (2004 ▶); Blue et al. (2006 ▶); Berger et al. (2012 ▶). For compounds with the 1,3-bis-(2,6-diisopropyl­phen­yl)imidazolium unit, see: Ikhile et al. (2010 ▶); Giffin et al. (2010 ▶).

Experimental

Crystal data

C27H37N2 +·Cl−·2CH2Cl2

M = 594.89

Monoclinic,

a = 9.1117 (4) Å

b = 16.4990 (8) Å

c = 10.8875 (6) Å

β = 101.068 (4)°

V = 1606.32 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.47 mm−1

T = 173 K

0.32 × 0.29 × 0.14 mm

Data collection

Stoe IPDS II two-circle diffractometer

Absorption correction: multi-scan (MULABS; Spek, 2009 ▶; Blessing, 1995 ▶) T min = 0.864, T max = 0.937

17793 measured reflections

2934 independent reflections

2648 reflections with I > 2σ(I)

R int = 0.067

Refinement

R[F 2 > 2σ(F 2)] = 0.075

wR(F 2) = 0.184

S = 1.04

2934 reflections

185 parameters

6 restraints

H-atom parameters constrained

Δρmax = 1.36 e Å−3

Δρmin = −1.60 e Å−3

Data collection: X-AREA (Stoe & Cie, 2001 ▶); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XP in SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812022234/ng5271sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022234/ng5271Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812022234/ng5271Isup3.cml

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

C27H37N2+·Cl−·2CH2Cl2	F(000) = 628
Mr = 594.89	Dx = 1.230 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 27732 reflections
a = 9.1117 (4) Å	θ = 3.3–28.0°
b = 16.4990 (8) Å	µ = 0.47 mm−1
c = 10.8875 (6) Å	T = 173 K
β = 101.068 (4)°	Plate, colourless
V = 1606.32 (14) Å3	0.32 × 0.29 × 0.14 mm
Z = 2

Stoe IPDS II two-circle diffractometer	2934 independent reflections
Radiation source: fine-focus sealed tube	2648 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
ω scans	θmax = 25.0°, θmin = 3.2°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −10→10
Tmin = 0.864, Tmax = 0.937	k = −19→19
17793 measured reflections	l = −12→12

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.184	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0696P)2 + 3.4645P] where P = (Fo2 + 2Fc2)/3
2934 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 1.36 e Å−3
6 restraints	Δρmin = −1.60 e Å−3

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	Occ. (<1)
Cl1	0.66661 (12)	0.2500	0.57563 (10)	0.0339 (3)
N1	0.2042 (3)	0.31549 (14)	0.5835 (2)	0.0248 (5)
C1	0.2891 (4)	0.2500	0.5788 (3)	0.0245 (8)
H1	0.3918	0.2500	0.5730	0.029*
C2	0.0606 (3)	0.29075 (18)	0.5907 (3)	0.0289 (6)
H2	−0.0222	0.3250	0.5948	0.035*
C11	0.2556 (3)	0.39874 (17)	0.5807 (3)	0.0298 (6)
C12	0.2225 (4)	0.44066 (19)	0.4672 (3)	0.0356 (7)
C13	0.2757 (4)	0.5201 (2)	0.4671 (3)	0.0484 (9)
H13	0.2547	0.5510	0.3921	0.058*
C14	0.3582 (5)	0.5546 (2)	0.5738 (4)	0.0571 (10)
H14	0.3955	0.6081	0.5711	0.068*
C15	0.3866 (5)	0.5115 (2)	0.6843 (4)	0.0503 (9)
H15	0.4419	0.5365	0.7574	0.060*
C16	0.3359 (4)	0.43202 (18)	0.6913 (3)	0.0358 (7)
C21	0.1357 (4)	0.4026 (2)	0.3483 (3)	0.0386 (7)
H21	0.1064	0.3468	0.3703	0.046*
C22	0.2339 (9)	0.3934 (6)	0.2452 (8)	0.054 (2)*	0.50
H22A	0.3048	0.3487	0.2676	0.081*	0.50
H22B	0.2890	0.4438	0.2393	0.081*	0.50
H22C	0.1691	0.3820	0.1643	0.081*	0.50
C23	−0.0049 (9)	0.4473 (5)	0.2962 (8)	0.0508 (18)*	0.50
H23A	0.0003	0.5021	0.3314	0.076*	0.50
H23B	−0.0905	0.4185	0.3180	0.076*	0.50
H23C	−0.0169	0.4505	0.2049	0.076*	0.50
C22'	0.2392 (8)	0.3593 (5)	0.2818 (7)	0.0421 (16)*	0.50
H22D	0.1995	0.3606	0.1916	0.063*	0.50
H22E	0.2495	0.3029	0.3105	0.063*	0.50
H22F	0.3373	0.3858	0.2994	0.063*	0.50
C23'	0.0432 (10)	0.4686 (5)	0.2642 (8)	0.055 (2)*	0.50
H23D	−0.0477	0.4442	0.2157	0.082*	0.50
H23E	0.1035	0.4912	0.2069	0.082*	0.50
H23F	0.0159	0.5120	0.3171	0.082*	0.50
C61	0.3705 (4)	0.3863 (2)	0.8146 (3)	0.0405 (8)
H61	0.3160	0.3334	0.8034	0.049*
C62	0.5383 (5)	0.3685 (3)	0.8486 (3)	0.0561 (10)
H62A	0.5600	0.3388	0.9281	0.084*
H62B	0.5941	0.4196	0.8571	0.084*
H62C	0.5680	0.3356	0.7826	0.084*
C63	0.3195 (4)	0.4323 (2)	0.9205 (3)	0.0484 (9)
H63A	0.3446	0.4008	0.9981	0.073*
H63B	0.2111	0.4406	0.8995	0.073*
H63C	0.3701	0.4849	0.9321	0.073*
C3	0.8708 (8)	0.2675 (6)	0.8843 (7)	0.065 (4)	0.50
H3A	0.8224	0.2614	0.7953	0.078*	0.50
H3B	0.7940	0.2572	0.9355	0.078*	0.50
Cl31	0.9337 (5)	0.3663 (3)	0.9093 (4)	0.1291 (19)	0.50
Cl32	1.0117 (5)	0.1947 (4)	0.9208 (3)	0.149 (2)	0.50
C4	0.7100 (8)	0.2771 (5)	1.2652 (7)	0.059 (2)	0.50
H4A	0.7124	0.3367	1.2759	0.070*	0.50
H4B	0.7219	0.2526	1.3495	0.070*	0.50
Cl41	0.8547 (2)	0.2500	1.20316 (19)	0.1263 (12)
Cl42	0.53459 (19)	0.2500	1.18007 (18)	0.0806 (6)

	U11	U22	U33	U12	U13	U23
Cl1	0.0375 (6)	0.0356 (6)	0.0296 (5)	0.000	0.0092 (4)	0.000
N1	0.0280 (12)	0.0222 (11)	0.0227 (11)	0.0004 (9)	0.0016 (9)	0.0000 (9)
C1	0.027 (2)	0.0238 (19)	0.0214 (18)	0.000	0.0013 (15)	0.000
C2	0.0276 (14)	0.0323 (14)	0.0268 (14)	0.0045 (12)	0.0057 (11)	0.0000 (12)
C11	0.0357 (15)	0.0213 (14)	0.0319 (15)	−0.0007 (12)	0.0049 (12)	0.0020 (11)
C12	0.0413 (17)	0.0313 (16)	0.0339 (16)	0.0033 (13)	0.0068 (13)	0.0055 (13)
C13	0.065 (2)	0.0337 (18)	0.046 (2)	−0.0017 (17)	0.0090 (17)	0.0153 (15)
C14	0.078 (3)	0.0266 (17)	0.064 (2)	−0.0151 (18)	0.007 (2)	0.0070 (17)
C15	0.067 (2)	0.0305 (17)	0.048 (2)	−0.0128 (17)	−0.0005 (18)	−0.0024 (15)
C16	0.0461 (18)	0.0249 (15)	0.0341 (16)	−0.0035 (13)	0.0021 (13)	−0.0012 (12)
C21	0.0444 (18)	0.0400 (18)	0.0304 (16)	0.0031 (14)	0.0048 (13)	0.0074 (13)
C61	0.057 (2)	0.0294 (16)	0.0303 (16)	−0.0070 (15)	−0.0027 (14)	−0.0027 (13)
C62	0.071 (3)	0.058 (2)	0.0366 (19)	0.023 (2)	0.0040 (17)	−0.0019 (17)
C63	0.050 (2)	0.054 (2)	0.0386 (18)	−0.0005 (17)	0.0038 (15)	−0.0060 (16)
C3	0.046 (4)	0.102 (14)	0.044 (3)	0.020 (5)	−0.001 (3)	0.011 (5)
Cl31	0.089 (3)	0.175 (5)	0.109 (3)	−0.071 (3)	−0.017 (2)	0.025 (3)
Cl32	0.116 (3)	0.282 (7)	0.0525 (16)	0.131 (4)	0.0274 (17)	0.040 (2)
C4	0.073 (5)	0.061 (6)	0.051 (4)	−0.013 (4)	0.034 (4)	−0.012 (3)
Cl41	0.0594 (11)	0.259 (4)	0.0599 (11)	0.000	0.0088 (9)	0.000
Cl42	0.0583 (10)	0.1116 (15)	0.0758 (11)	0.000	0.0227 (8)	0.000

N1—C1	1.335 (3)	C22'—H22D	0.9800
N1—C2	1.388 (4)	C22'—H22E	0.9800
N1—C11	1.453 (4)	C22'—H22F	0.9800
C1—N1i	1.335 (3)	C23'—H23D	0.9800
C1—H1	0.9500	C23'—H23E	0.9800
C2—C2i	1.345 (6)	C23'—H23F	0.9800
C2—H2	0.9500	C61—C63	1.525 (5)
C11—C16	1.395 (4)	C61—C62	1.531 (5)
C11—C12	1.398 (4)	C61—H61	1.0000
C12—C13	1.398 (5)	C62—H62A	0.9800
C12—C21	1.517 (4)	C62—H62B	0.9800
C13—C14	1.379 (5)	C62—H62C	0.9800
C13—H13	0.9500	C63—H63A	0.9800
C14—C15	1.378 (5)	C63—H63B	0.9800
C14—H14	0.9500	C63—H63C	0.9800
C15—C16	1.398 (5)	C3—Cl31	1.732 (11)
C15—H15	0.9500	C3—Cl32	1.748 (9)
C16—C61	1.519 (4)	C3—H3A	0.9900
C21—C22'	1.479 (8)	C3—H3B	0.9900
C21—C23	1.493 (8)	Cl31—Cl32i	1.225 (7)
C21—C23'	1.562 (9)	Cl32—Cl31i	1.225 (7)
C21—C22	1.572 (9)	Cl32—C3i	1.414 (9)
C21—H21	1.0000	Cl32—Cl32i	1.825 (13)
C22—H22A	0.9800	C4—Cl41	1.654 (7)
C22—H22B	0.9800	C4—Cl42	1.744 (7)
C22—H22C	0.9800	C4—H4A	0.9900
C23—H23A	0.9800	C4—H4B	0.9900
C23—H23B	0.9800	Cl41—C4i	1.654 (7)
C23—H23C	0.9800	Cl42—C4i	1.744 (7)
C1—N1—C2	108.9 (2)	C21—C23—H23C	109.5
C1—N1—C11	124.9 (2)	H23A—C23—H23C	109.5
C2—N1—C11	126.2 (2)	H23B—C23—H23C	109.5
N1i—C1—N1	108.0 (3)	C21—C22'—H22D	109.5
N1i—C1—H1	126.0	C21—C22'—H22E	109.5
N1—C1—H1	126.0	H22D—C22'—H22E	109.5
C2i—C2—N1	107.11 (15)	C21—C22'—H22F	109.5
C2i—C2—H2	126.4	H22D—C22'—H22F	109.5
N1—C2—H2	126.4	H22E—C22'—H22F	109.5
C16—C11—C12	123.8 (3)	C21—C23'—H23D	109.5
C16—C11—N1	118.1 (3)	C21—C23'—H23E	109.5
C12—C11—N1	118.1 (3)	H23D—C23'—H23E	109.5
C11—C12—C13	116.7 (3)	C21—C23'—H23F	109.5
C11—C12—C21	122.6 (3)	H23D—C23'—H23F	109.5
C13—C12—C21	120.8 (3)	H23E—C23'—H23F	109.5
C14—C13—C12	121.2 (3)	C16—C61—C63	112.3 (3)
C14—C13—H13	119.4	C16—C61—C62	109.7 (3)
C12—C13—H13	119.4	C63—C61—C62	110.4 (3)
C15—C14—C13	120.3 (3)	C16—C61—H61	108.1
C15—C14—H14	119.9	C63—C61—H61	108.1
C13—C14—H14	119.9	C62—C61—H61	108.1
C14—C15—C16	121.5 (3)	C61—C62—H62A	109.5
C14—C15—H15	119.3	C61—C62—H62B	109.5
C16—C15—H15	119.3	H62A—C62—H62B	109.5
C11—C16—C15	116.5 (3)	C61—C62—H62C	109.5
C11—C16—C61	123.6 (3)	H62A—C62—H62C	109.5
C15—C16—C61	119.9 (3)	H62B—C62—H62C	109.5
C22'—C21—C23	129.3 (5)	C61—C63—H63A	109.5
C22'—C21—C12	109.9 (4)	C61—C63—H63B	109.5
C23—C21—C12	112.9 (4)	H63A—C63—H63B	109.5
C22'—C21—C23'	111.9 (5)	C61—C63—H63C	109.5
C12—C21—C23'	110.2 (4)	H63A—C63—H63C	109.5
C23—C21—C22	109.9 (5)	H63B—C63—H63C	109.5
C12—C21—C22	112.0 (4)	Cl31—C3—Cl32	113.9 (5)
C23'—C21—C22	88.0 (5)	Cl31—C3—H3A	108.8
C22'—C21—H21	84.1	Cl32—C3—H3A	108.8
C23—C21—H21	107.2	Cl31—C3—H3B	108.8
C12—C21—H21	107.2	Cl32—C3—H3B	108.8
C23'—C21—H21	130.0	H3A—C3—H3B	107.7
C22—C21—H21	107.2	Cl32i—Cl31—C3	53.9 (4)
C21—C22—H22A	109.5	Cl31i—Cl32—C3i	81.7 (5)
C21—C22—H22B	109.5	Cl31i—Cl32—C3	98.9 (5)
H22A—C22—H22B	109.5	Cl31i—Cl32—Cl32i	145.3 (3)
C21—C22—H22C	109.5	Cl41—C4—Cl42	115.8 (4)
H22A—C22—H22C	109.5	Cl41—C4—H4A	108.3
H22B—C22—H22C	109.5	Cl42—C4—H4A	108.3
C21—C23—H23A	109.5	Cl41—C4—H4B	108.3
C21—C23—H23B	109.5	Cl42—C4—H4B	108.3
H23A—C23—H23B	109.5	H4A—C4—H4B	107.4
C2—N1—C1—N1i	−0.4 (4)	C14—C15—C16—C11	0.1 (6)
C11—N1—C1—N1i	179.95 (19)	C14—C15—C16—C61	179.5 (4)
C1—N1—C2—C2i	0.3 (2)	C11—C12—C21—C22'	−87.2 (5)
C11—N1—C2—C2i	179.9 (2)	C13—C12—C21—C22'	91.7 (5)
C1—N1—C11—C16	−79.7 (4)	C11—C12—C21—C23	120.6 (5)
C2—N1—C11—C16	100.8 (3)	C13—C12—C21—C23	−60.5 (6)
C1—N1—C11—C12	100.0 (4)	C11—C12—C21—C23'	149.1 (5)
C2—N1—C11—C12	−79.6 (4)	C13—C12—C21—C23'	−32.1 (5)
C16—C11—C12—C13	0.7 (5)	C11—C12—C21—C22	−114.7 (5)
N1—C11—C12—C13	−178.9 (3)	C13—C12—C21—C22	64.2 (5)
C16—C11—C12—C21	179.6 (3)	C11—C16—C61—C63	−125.9 (3)
N1—C11—C12—C21	0.0 (4)	C15—C16—C61—C63	54.7 (5)
C11—C12—C13—C14	0.7 (5)	C11—C16—C61—C62	110.9 (4)
C21—C12—C13—C14	−178.2 (4)	C15—C16—C61—C62	−68.4 (4)
C12—C13—C14—C15	−1.7 (7)	Cl32—C3—Cl31—Cl32i	4.6 (3)
C13—C14—C15—C16	1.2 (7)	Cl31—C3—Cl32—Cl31i	172.1 (6)
C12—C11—C16—C15	−1.1 (5)	Cl31—C3—Cl32—C3i	176.6 (3)
N1—C11—C16—C15	178.5 (3)	Cl31—C3—Cl32—Cl32i	−3.4 (3)
C12—C11—C16—C61	179.5 (3)	Cl42—C4—Cl41—C4i	−64.5 (5)
N1—C11—C16—C61	−0.9 (5)	Cl41—C4—Cl42—C4i	64.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.95	2.50	3.447 (4)	176

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl1	0.95	2.50	3.447 (4)	176