Crystal structure of 1,3-bis­(2,6-diiso­propyl­phen­yl)-4,5-dimethyl-1H-imid­azol-3-ium bromide di­chloro­methane disolvate

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

doi:10.1107/S1600536814023150

organic compounds

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ISSN: 2056-9890

Volume 70| Part 11| November 2014| Pages o1193-o1194

doi:10.1107/S1600536814023150

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Crystal structure of 1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium bromide dichloromethane disolvate

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

^aInstitut für Anorganische Chemie, J. W. Goethe-Universität Frankfurt, Max-von-Laue-Str. 7, 60438 Frankfurt/Main, Germany
^*Correspondence e-mail: bolte@chemie.uni-frankfurt.de

Edited by W. T. A. Harrison, University of Aberdeen, Scotland (Received 16 October 2014; accepted 21 October 2014; online 24 October 2014)

The title solvated salt, C₂₉H₄₁N₂⁺·Br⁻·2CH₂Cl₂ was obtained from the reaction of the Arduengo-type carbene 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-4,5-dimethyl-2H-imidazol-2-ylidene with Si₂Br₆ in dichloromethane. The complete cation is generated by a crystallographic mirror plane and the dihedral angle between the five-membered ring and the benzene ring is 89.8 (6)°; the dihedral angle between the benzene rings is 40.7 (2)°. The anion also lies on the mirror plane and both dichloromethane molecules are disordered across the mirror plane over two equally occupied orientations. In the crystal, the cations are linked to the anions via C—H⋯Br hydrogen bonds.

Keywords: Arduengo-type carbene; C—H⋯Br hydrogen bond; crystal structure.

CCDC reference: 1030231

1. Related literature

For the preparation of imidazolium salts, see: Arduengo et al. (1995 , 1999 ); Hintermann et al. (2007 ); Gaillard et al. (2009 ). For silylene stabilization, see: Wang et al. (2008 ); Ghadwal et al. (2009 ); Filippou et al. (2009 ). For structures with the same cation but different anions, see: Clavier et al. (2009 ); Gaillard et al. (2009). For other crystallographically characterized imidazolium structures, see: Arduengo et al. (1995, 1999); Fliedel et al. (2007 ); Hagos et al. (2008 ); Berger, Auner & Bolte (2012 ); Berger, Auner, Sinke & Bolte (2012 ); Ikhile & Bala (2010 ); Giffin et al. (2010 )

2. Experimental

2.1. Crystal data

C₂₉H₄₁N₂⁺·Br⁻·2CH₂Cl₂
M_r = 667.40
Monoclinic, P 2₁ /m
a = 10.0644 (11) Å
b = 16.6082 (17) Å
c = 10.7107 (15) Å
β = 98.48 (1)°
V = 1770.7 (4) Å³
Z = 2
Mo Kα radiation
μ = 1.48 mm⁻¹
T = 173 K
0.20 × 0.20 × 0.20 mm

2.2. Data collection

STOE IPDS II two-circle diffractometer
Absorption correction: multi-scan (X-AREA Stoe & Cie, 2001 ) T_min = 0.756, T_max = 0.756
21288 measured reflections
3229 independent reflections
2618 reflections with I > 2σ(I)
R_int = 0.156

2.3. Refinement

R[F² > 2σ(F²)] = 0.163
wR(F²) = 0.393
S = 1.12
3229 reflections
190 parameters
H-atom parameters constrained
Δρ_max = 1.09 e Å⁻³
Δρ_min = −1.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C—H⋯Br1	0.95	2.46	3.403 (13)	172

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2013, PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1030231

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814023150/hb7303sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814023150/hb7303Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814023150/hb7303Isup3.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). To block deprotonation and substitution reactions at the unsaturated backbone of the imidazolium skeleton, methyl groups adjacent to the C=C bond can decrease NHC reactivity and increase the steric demand at these carbon positions (Gaillard et al., 2009). Deprotonation of these imidazolium salts by strong bases gives the free stable NHC, which is widely used as a ligand for e.g. silylene stabilization (Wang et al., 2008; Ghadwal et al., 2009; Filippou et al., 2009).

The title compound crystallizes with discrete cations, anions and solvent dichloromethane molecules. The 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 Clavier et al. (2009) and Gaillard et al. (2009). For compounds with 1,3-Bis-(2,6-diisopropylphenyl)imidazolium unit, see: Ikhile et al. (2010), Giffin et al. (2010), Hagos et al. (2008), Fliedel et al. (2007), Berger, Auner & Bolte (2012); Berger, Auner, Sinke & Bolte (2012).

Related literature top

For the preparation of imidazolium salts, see: Arduengo et al. (1995, 1999); Hintermann et al. (2007); Gaillard et al. (2009). For silylene stabilization, see: Wang et al. (2008); Ghadwal et al. (2009); Filippou et al. (2009). For structures with the same cation but different anions, see: Clavier et al. (2009); Gaillard et al. (2009). For other crystallographically characterized imidazolium structures, see: Arduengo et al. (1995, 1999); Fliedel et al. (2007); Hagos et al. (2008); Berger, Auner & Bolte (2012); Berger, Auner, Sinke & Bolte (2012); Ikhile & Bala (2010); Giffin et al. (2010)

Experimental top

The title compound is synthesized according to Arduengo et al. (1995), Hintermann (2007) and Gaillard et al. (2009).

1,3-Bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium bromide chloroform disolvate was prepared by reacting 340 mg of 1,3-bis(2,6-diisopropylphenyl)-1,3-dihydro-4,5-dimethyl-2H- imidazol-2-ylidene with 300 mg of Si₂Br₆ in 10 ml dichloromethane. After removing the solvent in vacuo and dissolving the residue in CD₂Cl₂ the NMR-Tube was stored for two weeks at 253 K. Colourless needles of the title compound crystallized.

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: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2008), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

Figure 1. Perspective view of the title comopound with displacement ellipsoids drawn at the 50% probability level. The C—H···Br hydrogen bond is drawn as a dashed line. Atoms labelled with suffix A were generated by the symmetry operator x, -y + 1/2, z.

1,3-Bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium bromide dichloromethane disolvate top

Crystal data top

C₂₉H₄₁N₂⁺·Br⁻·2CH₂Cl₂	F(000) = 696
M_r = 667.40	D_x = 1.252 Mg m⁻³
Monoclinic, P2₁/m	Mo Kα radiation, λ = 0.71073 Å
a = 10.0644 (11) Å	Cell parameters from 20226 reflections
b = 16.6082 (17) Å	θ = 3.2–25.8°
c = 10.7107 (15) Å	µ = 1.48 mm⁻¹
β = 98.48 (1)°	T = 173 K
V = 1770.7 (4) Å³	Block, colourless
Z = 2	0.20 × 0.20 × 0.20 mm

Data collection top

STOE IPDS II two-circle diffractometer	2618 reflections with I > 2σ(I)
Radiation source: Genix 3D IµS microfocus X-ray source	R_int = 0.156
ω scans	θ_max = 25.0°, θ_min = 3.2°
Absorption correction: multi-scan (X-AREA Stoe & Cie, 2001)	h = −11→11
T_min = 0.756, T_max = 0.756	k = −19→19
21288 measured reflections	l = −12→12
3229 independent reflections

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.163	H-atom parameters constrained
wR(F²) = 0.393	w = 1/[σ²(F_o²) + (0.1372P)² + 27.7491P] where P = (F_o² + 2F_c²)/3
S = 1.12	(Δ/σ)_max < 0.001
3229 reflections	Δρ_max = 1.09 e Å⁻³
190 parameters	Δρ_min = −1.13 e Å⁻³

Crystal data top

C₂₉H₄₁N₂⁺·Br⁻·2CH₂Cl₂	V = 1770.7 (4) Å³
M_r = 667.40	Z = 2
Monoclinic, P2₁/m	Mo Kα radiation
a = 10.0644 (11) Å	µ = 1.48 mm⁻¹
b = 16.6082 (17) Å	T = 173 K
c = 10.7107 (15) Å	0.20 × 0.20 × 0.20 mm
β = 98.48 (1)°

Data collection top

STOE IPDS II two-circle diffractometer	3229 independent reflections
Absorption correction: multi-scan (X-AREA Stoe & Cie, 2001)	2618 reflections with I > 2σ(I)
T_min = 0.756, T_max = 0.756	R_int = 0.156
21288 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.163	0 restraints
wR(F²) = 0.393	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.1372P)² + 27.7491P] where P = (F_o² + 2F_c²)/3
3229 reflections	Δρ_max = 1.09 e Å⁻³
190 parameters	Δρ_min = −1.13 e Å⁻³

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. ;

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.7876 (7)	0.1843 (5)	0.4157 (7)	0.0283 (17)
C1	0.7093 (13)	0.2500	0.4193 (12)	0.026 (3)
H1	0.6157	0.2500	0.4235	0.031*
C2	0.9196 (9)	0.2098 (7)	0.4076 (9)	0.035 (2)
C3	1.0285 (10)	0.1493 (7)	0.4038 (12)	0.046 (3)
H3A	0.9910	0.0949	0.4060	0.069*
H3B	1.0982	0.1569	0.4770	0.069*
H3C	1.0678	0.1562	0.3261	0.069*
C4	0.6880 (14)	0.1029 (8)	0.1817 (11)	0.054 (3)
H4	0.7369	0.1553	0.1943	0.065*
C5	0.5431 (19)	0.1214 (12)	0.1280 (16)	0.092 (6)
H5A	0.5398	0.1470	0.0451	0.138*
H5B	0.5049	0.1580	0.1852	0.138*
H5C	0.4911	0.0714	0.1192	0.138*
C6	0.7583 (18)	0.0522 (12)	0.0899 (14)	0.081 (5)
H6A	0.8504	0.0401	0.1290	0.121*
H6B	0.7602	0.0824	0.0117	0.121*
H6C	0.7089	0.0017	0.0708	0.121*
C7	0.7974 (12)	0.1111 (8)	0.6591 (11)	0.048 (3)
H7	0.8410	0.1618	0.6351	0.057*
C8	0.9077 (15)	0.0617 (10)	0.7486 (13)	0.069 (4)
H8A	0.9385	0.0932	0.8247	0.103*
H8B	0.9840	0.0504	0.7039	0.103*
H8C	0.8689	0.0108	0.7723	0.103*
C9	0.6840 (16)	0.1355 (10)	0.7316 (13)	0.068 (4)
H9A	0.7215	0.1645	0.8085	0.102*
H9B	0.6370	0.0873	0.7544	0.102*
H9C	0.6206	0.1705	0.6785	0.102*
C11	0.7393 (10)	0.1030 (7)	0.4224 (10)	0.037 (2)
C12	0.6930 (11)	0.0638 (7)	0.3109 (11)	0.045 (3)
C13	0.6476 (13)	−0.0157 (8)	0.3211 (13)	0.056 (3)
H13	0.6160	−0.0452	0.2467	0.067*
C14	0.6482 (13)	−0.0516 (8)	0.4379 (13)	0.057 (3)
H14	0.6130	−0.1043	0.4434	0.068*
C15	0.6993 (12)	−0.0112 (8)	0.5450 (12)	0.048 (3)
H15	0.7018	−0.0373	0.6242	0.058*
C16	0.7483 (10)	0.0679 (7)	0.5420 (10)	0.040 (2)
Br1	0.36891 (18)	0.2500	0.4011 (2)	0.0582 (7)
C1L	0.250 (3)	0.2500	0.711 (3)	0.19 (3)
H1LA	0.2711	0.2180	0.6419	0.228*	0.5
H1LB	0.2390	0.3042	0.6806	0.228*	0.5
Cl1	0.3918 (6)	0.2500	0.8208 (6)	0.104 (3)
Cl2	0.1100 (7)	0.2217 (5)	0.7384 (7)	0.074 (2)	0.5
C2L	1.165 (2)	0.2500	0.089 (2)	0.090 (9)
H2LA	1.1999	0.2798	0.0233	0.108*	0.5
H2LB	1.2084	0.2646	0.1703	0.108*	0.5
Cl3	1.1536 (11)	0.1392 (7)	0.0594 (9)	0.100 (3)	0.5
Cl4	0.9934 (12)	0.2500	0.0734 (10)	0.253 (11)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.022 (4)	0.037 (4)	0.025 (4)	−0.004 (3)	0.001 (3)	0.001 (3)
C1	0.023 (6)	0.028 (7)	0.027 (6)	0.000	0.005 (5)	0.000
C2	0.019 (4)	0.046 (5)	0.036 (5)	0.011 (4)	−0.004 (4)	−0.003 (4)
C3	0.024 (5)	0.055 (7)	0.058 (7)	0.003 (5)	0.005 (5)	−0.013 (6)
C4	0.069 (8)	0.055 (8)	0.035 (6)	−0.007 (6)	−0.003 (5)	−0.009 (5)
C5	0.107 (14)	0.091 (13)	0.071 (10)	0.020 (11)	−0.013 (9)	−0.002 (9)
C6	0.086 (11)	0.101 (13)	0.051 (8)	−0.012 (10)	−0.004 (7)	0.001 (8)
C7	0.051 (7)	0.046 (7)	0.046 (6)	0.008 (6)	0.005 (5)	0.010 (5)
C8	0.070 (9)	0.079 (10)	0.050 (8)	0.015 (8)	−0.015 (7)	−0.005 (7)
C9	0.081 (10)	0.076 (10)	0.053 (8)	0.008 (8)	0.026 (7)	0.007 (7)
C11	0.025 (5)	0.047 (6)	0.038 (5)	0.006 (4)	0.000 (4)	0.002 (5)
C12	0.032 (5)	0.044 (7)	0.055 (7)	0.004 (5)	−0.002 (5)	0.002 (5)
C13	0.050 (7)	0.054 (8)	0.061 (8)	0.002 (6)	−0.004 (6)	−0.015 (6)
C14	0.051 (7)	0.047 (7)	0.068 (8)	−0.003 (6)	−0.005 (6)	0.001 (6)
C15	0.045 (6)	0.051 (7)	0.049 (7)	0.003 (5)	0.007 (5)	0.015 (6)
C16	0.032 (5)	0.050 (7)	0.039 (6)	0.009 (5)	0.010 (4)	0.009 (5)
Br1	0.0341 (9)	0.0750 (13)	0.0665 (12)	0.000	0.0107 (7)	0.000
C1L	0.08 (2)	0.44 (8)	0.048 (15)	0.000	0.014 (14)	0.000
Cl1	0.044 (3)	0.183 (8)	0.079 (4)	0.000	−0.006 (3)	0.000
Cl2	0.055 (4)	0.097 (7)	0.068 (4)	−0.026 (3)	0.002 (3)	−0.002 (3)
C2L	0.057 (13)	0.17 (3)	0.047 (12)	0.000	0.010 (10)	0.000
Cl3	0.111 (7)	0.106 (7)	0.076 (6)	−0.021 (6)	−0.009 (5)	−0.006 (5)
Cl4	0.119 (8)	0.56 (3)	0.081 (6)	0.000	0.031 (6)	0.000

Geometric parameters (Å, º) top

N1—C1	1.350 (11)	C8—H8C	0.9800
N1—C2	1.409 (12)	C9—H9A	0.9800
N1—C11	1.440 (14)	C9—H9B	0.9800
C1—N1ⁱ	1.350 (11)	C9—H9C	0.9800
C1—H1	0.9500	C11—C12	1.380 (16)
C2—C2ⁱ	1.34 (2)	C11—C16	1.398 (15)
C2—C3	1.492 (14)	C12—C13	1.406 (18)
C3—H3A	0.9800	C13—C14	1.385 (19)
C3—H3B	0.9800	C13—H13	0.9500
C3—H3C	0.9800	C14—C15	1.362 (18)
C4—C5	1.52 (2)	C14—H14	0.9500
C4—C12	1.523 (17)	C15—C16	1.405 (17)
C4—C6	1.54 (2)	C15—H15	0.9500
C4—H4	1.0000	C1L—Cl2	1.56 (3)
C5—H5A	0.9800	C1L—Cl2ⁱ	1.56 (3)
C5—H5B	0.9800	C1L—Cl1	1.71 (3)
C5—H5C	0.9800	C1L—H1LA	0.9592
C6—H6A	0.9800	C1L—H1LB	0.9585
C6—H6B	0.9800	Cl2—Cl2ⁱ	0.941 (16)
C6—H6C	0.9800	C2L—Cl4	1.71 (3)
C7—C16	1.466 (17)	C2L—Cl3	1.867 (12)
C7—C9	1.527 (17)	C2L—Cl3ⁱ	1.867 (12)
C7—C8	1.585 (17)	C2L—H2LA	0.9648
C7—H7	1.0000	C2L—H2LB	0.9468
C8—H8A	0.9800	Cl3—Cl4	2.465 (14)
C8—H8B	0.9800	Cl4—Cl3ⁱ	2.465 (14)

C1—N1—C2	108.6 (8)	C7—C9—H9A	109.5
C1—N1—C11	123.6 (8)	C7—C9—H9B	109.5
C2—N1—C11	127.8 (8)	H9A—C9—H9B	109.5
N1ⁱ—C1—N1	107.9 (11)	C7—C9—H9C	109.5
N1ⁱ—C1—H1	126.1	H9A—C9—H9C	109.5
N1—C1—H1	126.1	H9B—C9—H9C	109.5
C2ⁱ—C2—N1	107.5 (5)	C12—C11—C16	124.3 (11)
C2ⁱ—C2—C3	132.4 (6)	C12—C11—N1	118.2 (9)
N1—C2—C3	120.2 (10)	C16—C11—N1	117.4 (9)
C2—C3—H3A	109.5	C11—C12—C13	116.6 (11)
C2—C3—H3B	109.5	C11—C12—C4	123.2 (11)
H3A—C3—H3B	109.5	C13—C12—C4	120.2 (11)
C2—C3—H3C	109.5	C14—C13—C12	121.1 (12)
H3A—C3—H3C	109.5	C14—C13—H13	119.5
H3B—C3—H3C	109.5	C12—C13—H13	119.5
C5—C4—C12	109.4 (12)	C15—C14—C13	119.9 (12)
C5—C4—C6	112.0 (12)	C15—C14—H14	120.0
C12—C4—C6	112.9 (12)	C13—C14—H14	120.0
C5—C4—H4	107.4	C14—C15—C16	122.1 (11)
C12—C4—H4	107.4	C14—C15—H15	118.9
C6—C4—H4	107.4	C16—C15—H15	118.9
C4—C5—H5A	109.5	C11—C16—C15	115.8 (11)
C4—C5—H5B	109.5	C11—C16—C7	123.2 (10)
H5A—C5—H5B	109.5	C15—C16—C7	120.9 (10)
C4—C5—H5C	109.5	Cl2—C1L—Cl1	123.9 (16)
H5A—C5—H5C	109.5	Cl2ⁱ—C1L—Cl1	123.9 (16)
H5B—C5—H5C	109.5	Cl2—C1L—H1LA	106.5
C4—C6—H6A	109.5	Cl2ⁱ—C1L—H1LA	128.3
C4—C6—H6B	109.5	Cl1—C1L—H1LA	106.1
H6A—C6—H6B	109.5	Cl2—C1L—H1LB	106.4
C4—C6—H6C	109.5	Cl1—C1L—H1LB	106.2
H6A—C6—H6C	109.5	H1LA—C1L—H1LB	106.8
H6B—C6—H6C	109.5	Cl2ⁱ—Cl2—C1L	72.4 (5)
C16—C7—C9	112.5 (11)	Cl4—C2L—Cl3	86.9 (8)
C16—C7—C8	112.4 (10)	Cl4—C2L—Cl3ⁱ	86.9 (8)
C9—C7—C8	109.9 (11)	Cl3—C2L—Cl3ⁱ	160.3 (15)
C16—C7—H7	107.3	Cl4—C2L—H2LA	113.4
C9—C7—H7	107.3	Cl3—C2L—H2LA	113.8
C8—C7—H7	107.3	Cl3ⁱ—C2L—H2LA	52.5
C7—C8—H8A	109.5	Cl4—C2L—H2LB	114.0
C7—C8—H8B	109.5	Cl3—C2L—H2LB	114.6
H8A—C8—H8B	109.5	Cl3ⁱ—C2L—H2LB	85.0
C7—C8—H8C	109.5	H2LA—C2L—H2LB	112.0
H8A—C8—H8C	109.5	Cl3ⁱ—Cl4—Cl3	96.5 (6)
H8B—C8—H8C	109.5

C2—N1—C1—N1ⁱ	−1.0 (13)	C11—C12—C13—C14	0.8 (17)
C11—N1—C1—N1ⁱ	177.7 (6)	C4—C12—C13—C14	−178.3 (12)
C1—N1—C2—C2ⁱ	0.6 (8)	C12—C13—C14—C15	−3.1 (19)
C11—N1—C2—C2ⁱ	−178.0 (8)	C13—C14—C15—C16	2.1 (19)
C1—N1—C2—C3	179.2 (10)	C12—C11—C16—C15	−3.6 (15)
C11—N1—C2—C3	0.6 (15)	N1—C11—C16—C15	179.5 (9)
C1—N1—C11—C12	91.6 (12)	C12—C11—C16—C7	−179.8 (10)
C2—N1—C11—C12	−89.9 (12)	N1—C11—C16—C7	3.3 (15)
C1—N1—C11—C16	−91.3 (12)	C14—C15—C16—C11	1.1 (17)
C2—N1—C11—C16	87.2 (12)	C14—C15—C16—C7	177.4 (11)
C16—C11—C12—C13	2.6 (16)	C9—C7—C16—C11	104.4 (13)
N1—C11—C12—C13	179.5 (9)	C8—C7—C16—C11	−130.9 (12)
C16—C11—C12—C4	−178.2 (10)	C9—C7—C16—C15	−71.5 (14)
N1—C11—C12—C4	−1.3 (16)	C8—C7—C16—C15	53.1 (15)
C5—C4—C12—C11	−107.1 (14)	Cl1—C1L—Cl2—Cl2ⁱ	102.3 (9)
C6—C4—C12—C11	127.4 (13)	Cl3ⁱ—C2L—Cl3—Cl4	−72 (4)
C5—C4—C12—C13	72.0 (15)	Cl3—C2L—Cl4—Cl3ⁱ	−161.3 (14)
C6—C4—C12—C13	−53.5 (16)	Cl3ⁱ—C2L—Cl4—Cl3	161.3 (14)

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
C—H···Br1	0.95	2.46	3.403 (13)	172

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C—H···Br1	0.95	2.46	3.403 (13)	172

References

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Volume 70| Part 11| November 2014| Pages o1193-o1194

doi:10.1107/S1600536814023150

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

Crystal structure of 1,3-bis­­(2,6-diiso­propyl­phen­yl)-4,5-di­methyl-1H-imid­azol-3-ium bromide di­chloro­methane disolvate

1. Related literature

2. Experimental

2.1. Crystal data

2.2. Data collection

2.3. Refinement

Supporting information

References

organic compounds

Crystal structure of 1,3-bis(2,6-diisopropylphenyl)-4,5-dimethyl-1H-imidazol-3-ium bromide dichloromethane disolvate