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

In the title compound, C(27)H(37)N(2) (+)·Br(-)·2CH(2)Cl(2), both the cation and the anion are 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. 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 = 639.35

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.090

S = 1.03

3200 reflections

197 parameters

H-atom parameters constrained

Δρmax = 0.43 e Å−3

Δρmin = −0.36 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/S1600536812022246/ng5272sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812022246/ng5272Isup3.cml

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

C27H37N2+·Br−·2CH2Cl2	F(000) = 664
Mr = 639.35	Dx = 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

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	Rint = 0.084
ω scans	θmax = 25.7°, θmin = 3.4°
Absorption correction: multi-scan (MULABS; Spek, 2009; Blessing, 1995)	h = −11→11
Tmin = 0.489, Tmax = 0.700	k = −19→20
20988 measured reflections	l = −13→13

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(Fo2) + (0.041P)2 + 0.9357P] where P = (Fo2 + 2Fc2)/3
3200 reflections	(Δ/σ)max < 0.001
197 parameters	Δρmax = 0.43 e Å−3
0 restraints	Δρmin = −0.36 e Å−3

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.

	x	y	z	Uiso*/Ueq	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

	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)

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)

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

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