Crystal structure of 1,3-bis-(2,6-diiso-propyl-phen-yl)-4,5-dimethyl-1H-imid-azol-3-ium bromide di-chloro-methane disolvate.

The title solvated salt, C29H41N2 (+)·Br(-)·2CH2Cl2 was obtained from the reaction of the Arduengo-type carbene 1,3-bis-(2,6-diiso-propyl-phen-yl)-1,3-dihydro-4,5-dimethyl-2H-imidazol-2-ylidene with Si2Br6 in di-chloro-methane. 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 di-chloro-methane mol-ecules 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.

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 ▶)

Experimental

Crystal data

C29H41N2 +·Br−·2CH2Cl2

M = 667.40

Monoclinic,

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

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

Refinement

R[F 2 > 2σ(F 2)] = 0.163

wR(F 2) = 0.393

S = 1.12

3229 reflections

190 parameters

H-atom parameters constrained

Δρmax = 1.09 e Å−3

Δρmin = −1.13 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814023150/hb7303sup1.cif

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

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814023150/hb7303Isup3.cml

Click here for additional data file.

x y z . DOI: 10.1107/S1600536814023150/hb7303fig1.tif

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 + , z.

CCDC reference: 1030231

Additional supporting information: crystallographic information; 3D view; checkCIF report

C29H41N2+·Br−·2CH2Cl2	F(000) = 696
Mr = 667.40	Dx = 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

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

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(Fo2) + (0.1372P)2 + 27.7491P] where P = (Fo2 + 2Fc2)/3
S = 1.12	(Δ/σ)max < 0.001
3229 reflections	Δρmax = 1.09 e Å−3
190 parameters	Δρmin = −1.13 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. ;

	x	y	z	Uiso*/Ueq	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)

	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

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)

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

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
CHBr1	0.95	2.46	3.403(13)	172