1,3-Bis(2,6-diisopropyl­phen­yl)-1H-imidazol-3-ium chloride dichloro­methane disolvate

Berger, M.; Auner, N.; Bolte, M.

doi:10.1107/S1600536812022234

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1844

doi:10.1107/S1600536812022234

Open

access

1,3-Bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride dichloromethane disolvate

Matthias Berger,^a Norbert Auner ^a and Michael Bolte ^a ^*

^aInstitut für Anorganische und Analytische Chemie, Goethe-Universität Frankfurt, Max-von-Laue-Strasse 7, 60438 Frankfurt am Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

(Received 10 May 2012; accepted 16 May 2012; online 23 May 2012)

In the title compound, C₂₇H₃₇N₂⁺·Cl⁻·2CH₂Cl₂, the cation and the anion are each located on a crystallographic mirror plane. Both of the dichloromethane solvent molecules 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_r = 594.89
Monoclinic, P 2₁ /m
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[F² > 2σ(F²)] = 0.075
wR(F²) = 0.184
S = 1.04
2934 reflections
185 parameters
6 restraints
H-atom parameters constrained
Δρ_max = 1.36 e Å⁻³
Δρ_min = −1.60 e Å⁻³

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

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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812022234/ng5271sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812022234/ng5271Isup3.cml

checkCIF report

Comment top

Imidazolium salts are precursors for the synthesis of N-heterocyclic carbenes (NHC) and can be prepared according to Arduengo et al. (1995, 1999) and Hintermann (2007). Deprotonation by strong bases gives the free stable NHC, which is widely used as ligands.

The title compound crystallizes with discrete cations, anions and solvent dichloromethane molecules. Both cations and anions are located on a crystallographic mirror plane. Both dichloromethane molecules show a disorder across a mirror plane over two equally occupied positions. Additionally, one isopropyl group is disordered as well. The Cl anions are connnected to the cations via C—H···Cl hydrogen bonds. Structures with the same cation, but with different anions and solvent molecules, have been determined by Stasch et al. (2004), Blue et al. (2006) and Berger et al. (2012). For the compounds with 1,3-bis-(2,6-diisopropylphenyl)imidazolium unit, see: Ikhile et al. (2010) and Giffin et al. (2010).

Related literature top

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 top

1,3-Bis(2,6-di-isopropylphenyl)1H-imidazol-3-ium chloride chloroform disolvate was prepared by reacting 0.05 g of 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene with 0.05 ml of SiCl₄ in deuterated dichloromethane. After two weeks at 253 K colorless needles of the title compound crystallized in the NMR-Tube.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); 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 (Sheldrick, 2008).

Figures top

Fig. 1. A perspective view of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bonds are shown as dashed lines. The minor occupied methyl groups, H atoms not involved in hydrogen bonding and dichloromethane molecules are omitted for clarity. Atoms labelled with suffix A were generated by the symmetry operator x, -y + 3/2, z.

1,3-Bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride dichloromethane disolvate top

Crystal data top

C₂₇H₃₇N₂⁺·Cl⁻·2CH₂Cl₂	F(000) = 628
M_r = 594.89	D_x = 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

Data collection top

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

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.184	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0696P)² + 3.4645P] where P = (F_o² + 2F_c²)/3
2934 reflections	(Δ/σ)_max < 0.001
185 parameters	Δρ_max = 1.36 e Å⁻³
6 restraints	Δρ_min = −1.60 e Å⁻³

Crystal data top

C₂₇H₃₇N₂⁺·Cl⁻·2CH₂Cl₂	V = 1606.32 (14) Å³
M_r = 594.89	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 9.1117 (4) Å	µ = 0.47 mm⁻¹
b = 16.4990 (8) Å	T = 173 K
c = 10.8875 (6) Å	0.32 × 0.29 × 0.14 mm
β = 101.068 (4)°

Data collection top

Stoe IPDS II two-circle diffractometer	2934 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	2648 reflections with I > 2σ(I)
T_min = 0.864, T_max = 0.937	R_int = 0.067
17793 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	6 restraints
wR(F²) = 0.184	H-atom parameters constrained
S = 1.04	Δρ_max = 1.36 e Å⁻³
2934 reflections	Δρ_min = −1.60 e Å⁻³
185 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	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)

Atomic displacement parameters (Å²) top

	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

Geometric parameters (Å, º) top

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)

Symmetry code: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₂₇H₃₇N₂⁺·Cl⁻·2CH₂Cl₂
M_r	594.89
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	173
a, b, c (Å)	9.1117 (4), 16.4990 (8), 10.8875 (6)
β (°)	101.068 (4)
V (Å³)	1606.32 (14)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.47
Crystal size (mm)	0.32 × 0.29 × 0.14

Data collection
Diffractometer	Stoe IPDS II two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.864, 0.937
No. of measured, independent and observed [I > 2σ(I)] reflections	17793, 2934, 2648
R_int	0.067
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.184, 1.04
No. of reflections	2934
No. of parameters	185
No. of restraints	6
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.36, −1.60

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.95	2.50	3.447 (4)	175.7

References

Arduengo, A. J., Goerlich, J. R. & Marshall, W. J. (1995). J. Am. Chem. Soc. 117, 11027–11028. CrossRef CAS Web of Science Google Scholar
Arduengo, A. J., Krafczyk, R., Schmutzler, R., Craig, H. A., Goerlich, J. R., Marshall, W. J. & Unverzagt, M. (1999). Tetrahedron, 55, 14523–14534. Web of Science CSD CrossRef CAS Google Scholar
Berger, M., Auner, N., Sinke, T. & Bolte, M. (2012). Acta Cryst. E68, o1845. CSD CrossRef IUCr Journals Google Scholar
Blessing, R. H. (1995). Acta Cryst. A51, 33–38. CrossRef CAS Web of Science IUCr Journals Google Scholar
Blue, E. D., Gunnoe, T. B., Petersen, J. L. & Boyle, P. D. (2006). J. Organomet. Chem. 691, 5988–5993. Web of Science CSD CrossRef CAS Google Scholar
Giffin, N. A., Hendsbee, A. D. & Masuda, J. D. (2010). Acta Cryst. E66, o2090–o2091. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hintermann, L. (2007). Beilstein J. Org. Chem. 3 No. 22. doi:10.1186/1860-5397-3-22. Google Scholar
Ikhile, M. I. & Bala, M. D. (2010). Acta Cryst. E66, o3121. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stasch, A., Singh, S., Roesky, H. W., Noltemeyer, M. & Schmidt, H.-G. (2004). Eur. J. Inorg. Chem. pp. 4052–4055. Web of Science CSD CrossRef Google Scholar
Stoe & Cie (2001). X-AREA. Stoe & Cie, Darmstadt, Germany. Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1844

doi:10.1107/S1600536812022234

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

1,3-Bis(2,6-diiso­propyl­phen­yl)-1H-imidazol-3-ium chloride di­chloro­methane disolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

1,3-Bis(2,6-diisopropylphenyl)-1H-imidazol-3-ium chloride dichloromethane disolvate