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

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

doi:10.1107/S1600536812022246

organic compounds

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Volume 68| Part 6| June 2012| Page o1845

doi:10.1107/S1600536812022246

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

Matthias Berger,^a Norbert Auner,^a Tanja Sinke ^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⁺·Br⁻·2CH₂Cl₂, both the cation and the anion are located on a crystallographic mirror plane. Both of the dichloromethane solvent molecules show a disorder across a mirror plane over two equally occupied positions. In the crystal, the cations are connnected to the bromide ions via C—H⋯Br 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⁺·Br⁻·2CH₂Cl₂
M_r = 639.35
Monoclinic, P 2₁ /m
a = 9.1874 (8) Å
b = 16.5165 (12) Å
c = 11.030 (1) Å
β = 102.332 (7)°
V = 1635.1 (2) Å³
Z = 2
Mo Kα radiation
μ = 1.60 mm⁻¹
T = 173 K
0.52 × 0.28 × 0.24 mm

Data collection

Stoe IPDS II two-circle diffractometer
Absorption correction: multi-scan (MULABS; Spek, 2009 ; Blessing, 1995 ) T_min = 0.489, T_max = 0.700
20988 measured reflections
3200 independent reflections
2867 reflections with I > 2σ(I)
R_int = 0.084

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.090
S = 1.03
3200 reflections
197 parameters
H-atom parameters constrained
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Br1	0.95	2.59	3.538 (3)	175

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/S1600536812022246/ng5272sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812022246/ng5272Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812022246/ng5272Isup3.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. The Br anions are connnected to the cations via C—H···Br 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 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 bromide chloroform disolvate was prepared by reacting 167 mg of 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-2H-imidazol-2-ylidene with 115 mg of Si₂Br₆ 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. 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 + 1/2, z.

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

Crystal data top

C₂₇H₃₇N₂⁺·Br⁻·2CH₂Cl₂	F(000) = 664
M_r = 639.35	D_x = 1.299 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 19135 reflections
a = 9.1874 (8) Å	θ = 3.4–26.0°
b = 16.5165 (12) Å	µ = 1.60 mm⁻¹
c = 11.030 (1) Å	T = 173 K
β = 102.332 (7)°	Plate, colourless
V = 1635.1 (2) Å³	0.52 × 0.28 × 0.24 mm
Z = 2

Data collection top

Stoe IPDS II two-circle diffractometer	3200 independent reflections
Radiation source: Genix 3D IµS microfocus X-ray source	2867 reflections with I > 2σ(I)
Genix 3D multilayer optics monochromator	R_int = 0.084
ω scans	θ_max = 25.7°, θ_min = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −11→11
T_min = 0.489, T_max = 0.700	k = −19→20
20988 measured reflections	l = −13→13

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.090	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.041P)² + 0.9357P] where P = (F_o² + 2F_c²)/3
3200 reflections	(Δ/σ)_max < 0.001
197 parameters	Δρ_max = 0.43 e Å⁻³
0 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₂₇H₃₇N₂⁺·Br⁻·2CH₂Cl₂	V = 1635.1 (2) Å³
M_r = 639.35	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 9.1874 (8) Å	µ = 1.60 mm⁻¹
b = 16.5165 (12) Å	T = 173 K
c = 11.030 (1) Å	0.52 × 0.28 × 0.24 mm
β = 102.332 (7)°

Data collection top

Stoe IPDS II two-circle diffractometer	3200 independent reflections
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	2867 reflections with I > 2σ(I)
T_min = 0.489, T_max = 0.700	R_int = 0.084
20988 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.090	H-atom parameters constrained
S = 1.03	Δρ_max = 0.43 e Å⁻³
3200 reflections	Δρ_min = −0.36 e Å⁻³
197 parameters

Special details top

Experimental. ;

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)
N1	0.29660 (18)	0.18481 (10)	0.41051 (15)	0.0255 (4)
C1	0.2134 (3)	0.2500	0.4158 (3)	0.0241 (6)
H1	0.1119	0.2500	0.4222	0.029*
C2	0.4378 (2)	0.20927 (14)	0.4033 (2)	0.0313 (5)
H2	0.5197	0.1751	0.3992	0.038*
C3	0.1307 (3)	0.11525 (15)	0.1796 (2)	0.0440 (6)
H3	0.1846	0.1682	0.1925	0.053*
C4	−0.0359 (4)	0.1327 (2)	0.1415 (3)	0.0594 (8)
H4A	−0.0567	0.1626	0.0629	0.089*
H4B	−0.0669	0.1652	0.2059	0.089*
H4C	−0.0911	0.0815	0.1311	0.089*
C5	0.1838 (3)	0.0696 (2)	0.0773 (3)	0.0545 (7)
H5A	0.1607	0.1012	0.0004	0.082*
H5B	0.1333	0.0171	0.0640	0.082*
H5C	0.2917	0.0611	0.1017	0.082*
C6	0.3631 (3)	0.09778 (16)	0.6435 (2)	0.0394 (5)
H6	0.4138	0.1470	0.6197	0.047*
C7	0.2619 (4)	0.1250 (3)	0.7253 (4)	0.0934 (15)
H7A	0.1868	0.1621	0.6791	0.140*
H7B	0.3203	0.1529	0.7980	0.140*
H7C	0.2123	0.0779	0.7523	0.140*
C8	0.4824 (5)	0.0423 (3)	0.7119 (4)	0.1023 (17)
H8A	0.5472	0.0256	0.6565	0.153*
H8B	0.4361	−0.0057	0.7401	0.153*
H8C	0.5415	0.0707	0.7838	0.153*
C11	0.2443 (2)	0.10184 (13)	0.4124 (2)	0.0317 (5)
C12	0.1641 (3)	0.06934 (14)	0.3013 (2)	0.0382 (5)
C13	0.1118 (4)	−0.00958 (16)	0.3072 (3)	0.0531 (7)
H13	0.0559	−0.0343	0.2342	0.064*
C14	0.1396 (4)	−0.05222 (16)	0.4166 (3)	0.0578 (8)
H14	0.1019	−0.1057	0.4183	0.069*
C15	0.2209 (3)	−0.01857 (16)	0.5234 (3)	0.0500 (7)
H15	0.2401	−0.0494	0.5978	0.060*
C16	0.2761 (3)	0.06008 (14)	0.5248 (2)	0.0366 (5)
Br1	−0.17082 (3)	0.2500	0.41902 (3)	0.03239 (11)
C9	0.6207 (8)	0.2781 (5)	0.1008 (6)	0.083 (4)	0.50
H9A	0.6687	0.2735	0.1899	0.100*	0.309 (13)
H9B	0.6987	0.2657	0.0540	0.100*	0.309 (13)
H9C	0.6825	0.2561	0.0452	0.100*	0.191 (13)
H9D	0.6666	0.2661	0.1886	0.100*	0.191 (13)
Cl1	0.5757 (3)	0.3808 (3)	0.0739 (3)	0.1306 (12)	0.50
Cl2	0.4398 (9)	0.2500	0.0600 (7)	0.091 (3)	0.38 (3)
Cl2'	0.4863 (16)	0.1966 (13)	0.0681 (6)	0.129 (7)	0.309 (13)
C10	0.7893 (8)	0.2231 (4)	0.7366 (6)	0.0643 (18)	0.50
H10A	0.7776	0.2363	0.6475	0.077*	0.50
H10B	0.7760	0.1639	0.7438	0.077*	0.50
Cl3	0.96814 (15)	0.2500	0.81560 (13)	0.0802 (4)
Cl4	0.6535 (2)	0.27308 (11)	0.79502 (16)	0.0803 (7)	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0245 (9)	0.0254 (8)	0.0255 (8)	0.0012 (7)	0.0030 (7)	−0.0009 (7)
C1	0.0239 (14)	0.0225 (14)	0.0246 (14)	0.000	0.0022 (11)	0.000
C2	0.0247 (10)	0.0374 (11)	0.0322 (11)	0.0053 (9)	0.0074 (8)	−0.0019 (9)
C3	0.0606 (16)	0.0333 (12)	0.0331 (12)	−0.0058 (12)	−0.0012 (11)	−0.0042 (10)
C4	0.074 (2)	0.0622 (19)	0.0383 (14)	0.0213 (16)	0.0033 (13)	−0.0042 (13)
C5	0.0549 (17)	0.0630 (18)	0.0446 (15)	0.0006 (15)	0.0085 (13)	−0.0039 (14)
C6	0.0428 (13)	0.0418 (13)	0.0325 (12)	0.0040 (11)	0.0055 (10)	0.0051 (10)
C7	0.057 (2)	0.142 (4)	0.081 (3)	0.000 (2)	0.0153 (19)	−0.065 (3)
C8	0.100 (3)	0.100 (3)	0.080 (3)	0.056 (3)	−0.042 (2)	−0.025 (2)
C11	0.0341 (12)	0.0226 (10)	0.0381 (12)	0.0013 (9)	0.0073 (9)	−0.0009 (9)
C12	0.0456 (14)	0.0276 (11)	0.0384 (12)	−0.0020 (10)	0.0025 (10)	−0.0018 (10)
C13	0.071 (2)	0.0321 (13)	0.0501 (16)	−0.0120 (13)	0.0003 (14)	−0.0050 (12)
C14	0.081 (2)	0.0268 (13)	0.0620 (18)	−0.0124 (13)	0.0074 (16)	0.0036 (12)
C15	0.0673 (19)	0.0345 (13)	0.0484 (15)	−0.0004 (13)	0.0128 (14)	0.0118 (11)
C16	0.0396 (13)	0.0321 (12)	0.0381 (12)	0.0050 (10)	0.0082 (10)	0.0048 (10)
Br1	0.02843 (17)	0.03733 (18)	0.03321 (18)	0.000	0.01058 (12)	0.000
C9	0.056 (3)	0.148 (12)	0.041 (3)	−0.028 (4)	−0.003 (2)	−0.009 (4)
Cl1	0.0784 (17)	0.170 (3)	0.129 (2)	0.0489 (19)	−0.0110 (16)	−0.020 (2)
Cl2	0.068 (3)	0.144 (9)	0.063 (3)	0.000	0.019 (2)	0.000
Cl2'	0.094 (7)	0.234 (17)	0.063 (2)	−0.100 (10)	0.024 (3)	−0.035 (5)
C10	0.084 (4)	0.064 (4)	0.056 (3)	−0.011 (3)	0.039 (3)	−0.015 (3)
Cl3	0.0666 (8)	0.1076 (11)	0.0723 (8)	0.000	0.0278 (6)	0.000
Cl4	0.0721 (10)	0.099 (2)	0.0690 (9)	0.0362 (10)	0.0134 (8)	−0.0046 (9)

Geometric parameters (Å, º) top

N1—C1	1.329 (2)	C11—C12	1.395 (3)
N1—C2	1.377 (3)	C12—C13	1.396 (4)
N1—C11	1.454 (3)	C13—C14	1.373 (4)
C1—N1ⁱ	1.329 (2)	C13—H13	0.9500
C1—H1	0.9500	C14—C15	1.371 (4)
C2—C2ⁱ	1.346 (5)	C14—H14	0.9500
C2—H2	0.9500	C15—C16	1.393 (4)
C3—C12	1.515 (3)	C15—H15	0.9500
C3—C5	1.521 (4)	C9—Cl2	1.691 (10)
C3—C4	1.525 (4)	C9—Cl1	1.757 (10)
C3—H3	1.0000	C9—Cl2'	1.810 (11)
C4—H4A	0.9800	C9—H9A	0.9900
C4—H4B	0.9800	C9—H9B	0.9900
C4—H4C	0.9800	C9—H9C	0.9900
C5—H5A	0.9800	C9—H9D	0.9900
C5—H5B	0.9800	Cl1—Cl2'ⁱ	1.51 (3)
C5—H5C	0.9800	Cl2—C9ⁱ	1.691 (10)
C6—C7	1.496 (4)	Cl2'—C9ⁱ	1.280 (11)
C6—C8	1.503 (4)	Cl2'—Cl1ⁱ	1.51 (3)
C6—C16	1.514 (3)	Cl2'—Cl2'ⁱ	1.76 (4)
C6—H6	1.0000	C10—Cl4	1.731 (6)
C7—H7A	0.9800	C10—Cl3	1.745 (7)
C7—H7B	0.9800	C10—H10A	0.9900
C7—H7C	0.9800	C10—H10B	0.9900
C8—H8A	0.9800	Cl3—C10ⁱ	1.745 (7)
C8—H8B	0.9800	Cl4—Cl4ⁱ	0.763 (4)
C8—H8C	0.9800	Cl4—C10ⁱ	1.523 (6)
C11—C16	1.394 (3)

C1—N1—C2	108.82 (18)	H8A—C8—H8C	109.5
C1—N1—C11	124.62 (18)	H8B—C8—H8C	109.5
C2—N1—C11	126.56 (18)	C16—C11—C12	124.2 (2)
N1ⁱ—C1—N1	108.2 (3)	C16—C11—N1	118.2 (2)
N1ⁱ—C1—H1	125.9	C12—C11—N1	117.7 (2)
N1—C1—H1	125.9	C11—C12—C13	116.2 (2)
C2ⁱ—C2—N1	107.06 (12)	C11—C12—C3	123.7 (2)
C2ⁱ—C2—H2	126.5	C13—C12—C3	120.1 (2)
N1—C2—H2	126.5	C14—C13—C12	121.2 (3)
C12—C3—C5	111.9 (2)	C14—C13—H13	119.4
C12—C3—C4	109.9 (2)	C12—C13—H13	119.4
C5—C3—C4	110.6 (2)	C15—C14—C13	120.8 (2)
C12—C3—H3	108.1	C15—C14—H14	119.6
C5—C3—H3	108.1	C13—C14—H14	119.6
C4—C3—H3	108.1	C14—C15—C16	121.2 (2)
C3—C4—H4A	109.5	C14—C15—H15	119.4
C3—C4—H4B	109.5	C16—C15—H15	119.4
H4A—C4—H4B	109.5	C15—C16—C11	116.4 (2)
C3—C4—H4C	109.5	C15—C16—C6	121.1 (2)
H4A—C4—H4C	109.5	C11—C16—C6	122.5 (2)
H4B—C4—H4C	109.5	Cl2—C9—Cl1	92.2 (4)
C3—C5—H5A	109.5	Cl2—C9—H9A	116.6
C3—C5—H5B	109.5	Cl1—C9—H9A	106.3
H5A—C5—H5B	109.5	Cl2'—C9—H9A	106.3
C3—C5—H5C	109.5	Cl2—C9—H9B	125.7
H5A—C5—H5C	109.5	Cl1—C9—H9B	106.3
H5B—C5—H5C	109.5	Cl2'—C9—H9B	106.3
C7—C6—C8	111.2 (3)	H9A—C9—H9B	106.4
C7—C6—C16	111.3 (2)	Cl2—C9—H9C	113.3
C8—C6—C16	112.1 (2)	Cl1—C9—H9C	113.3
C7—C6—H6	107.3	Cl2—C9—H9D	113.3
C8—C6—H6	107.3	Cl1—C9—H9D	113.3
C16—C6—H6	107.3	Cl2'—C9—H9D	100.2
C6—C7—H7A	109.5	H9C—C9—H9D	110.6
C6—C7—H7B	109.5	Cl2'ⁱ—Cl1—C9	45.3 (3)
H7A—C7—H7B	109.5	Cl1ⁱ—Cl2'—C9	106.2 (9)
C6—C7—H7C	109.5	Cl4—C10—Cl3	111.7 (3)
H7A—C7—H7C	109.5	Cl4—C10—H10A	109.3
H7B—C7—H7C	109.5	Cl3—C10—H10A	109.3
C6—C8—H8A	109.5	Cl4—C10—H10B	109.3
C6—C8—H8B	109.5	Cl3—C10—H10B	109.3
H8A—C8—H8B	109.5	H10A—C10—H10B	107.9
C6—C8—H8C	109.5

C2—N1—C1—N1ⁱ	0.8 (3)	C12—C11—C16—C15	−0.9 (4)
C11—N1—C1—N1ⁱ	−179.28 (14)	N1—C11—C16—C15	178.5 (2)
C1—N1—C2—C2ⁱ	−0.50 (18)	C12—C11—C16—C6	−179.8 (2)
C11—N1—C2—C2ⁱ	179.60 (16)	N1—C11—C16—C6	−0.4 (3)
C1—N1—C11—C16	−98.5 (3)	C7—C6—C16—C15	−77.5 (4)
C2—N1—C11—C16	81.4 (3)	C8—C6—C16—C15	47.7 (4)
C1—N1—C11—C12	81.0 (3)	C7—C6—C16—C11	101.3 (3)
C2—N1—C11—C12	−99.1 (3)	C8—C6—C16—C11	−133.5 (3)
C16—C11—C12—C13	1.2 (4)	Cl2—C9—Cl1—Cl2'ⁱ	2.7 (5)
N1—C11—C12—C13	−178.1 (2)	Cl2'—C9—Cl1—Cl2'ⁱ	7.6 (4)
C16—C11—C12—C3	−179.8 (2)	Cl1—C9—Cl2—C9ⁱ	174.0 (2)
N1—C11—C12—C3	0.8 (4)	Cl2'—C9—Cl2—C9ⁱ	1.6 (6)
C5—C3—C12—C11	124.9 (3)	Cl2—C9—Cl2'—C9ⁱ	−177.7 (8)
C4—C3—C12—C11	−111.8 (3)	Cl1—C9—Cl2'—C9ⁱ	173.1 (2)
C5—C3—C12—C13	−56.2 (4)	Cl2—C9—Cl2'—Cl1ⁱ	175.3 (9)
C4—C3—C12—C13	67.1 (3)	Cl1—C9—Cl2'—Cl1ⁱ	166.1 (5)
C11—C12—C13—C14	−0.5 (4)	Cl2—C9—Cl2'—Cl2'ⁱ	2.3 (8)
C3—C12—C13—C14	−179.5 (3)	Cl1—C9—Cl2'—Cl2'ⁱ	−6.9 (2)
C12—C13—C14—C15	−0.6 (5)	Cl4—C10—Cl3—C10ⁱ	−50.6 (3)
C13—C14—C15—C16	0.9 (5)	Cl3—C10—Cl4—Cl4ⁱ	−121.8 (4)
C14—C15—C16—C11	−0.2 (4)	Cl3—C10—Cl4—C10ⁱ	58.2 (4)
C14—C15—C16—C6	178.7 (3)

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···Br1	0.95	2.59	3.538 (3)	175

Experimental details

Crystal data
Chemical formula	C₂₇H₃₇N₂⁺·Br⁻·2CH₂Cl₂
M_r	639.35
Crystal system, space group	Monoclinic, P2₁/m
Temperature (K)	173
a, b, c (Å)	9.1874 (8), 16.5165 (12), 11.030 (1)
β (°)	102.332 (7)
V (Å³)	1635.1 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.60
Crystal size (mm)	0.52 × 0.28 × 0.24

Data collection
Diffractometer	Stoe IPDS II two-circle diffractometer
Absorption correction	Multi-scan (MULABS; Spek, 2009; Blessing, 1995)
T_min, T_max	0.489, 0.700
No. of measured, independent and observed [I > 2σ(I)] reflections	20988, 3200, 2867
R_int	0.084
(sin θ/λ)_max (Å⁻¹)	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.090, 1.03
No. of reflections	3200
No. of parameters	197
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.36

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···Br1	0.95	2.59	3.538 (3)	175.1

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. & Bolte, M. (2012). Acta Cryst. E68, o1844. 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

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Volume 68| Part 6| June 2012| Page o1845

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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 bromide di­chloro­methane disolvate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

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