4,5-Dibromo-1,2-dimethyl-1H-imidazol-3-ium bromide.

In the title salt, C(5)H(7)Br(2)N(2) (+)·Br(-), the cation and anion are connected by an N-H⋯Br hydrogen bond. In the crystal, there are inter-calated layers parallel to (10-2) in which bromide ions are located between the cations. Weak inter-molecular C-H⋯Br hydrogen bonds are also observed.

Related literature

For the preparation of the title compound using the Ortoleva–King reaction, see: King (1944 ▶). For applications of C,N-substituted haloimidazole derivatives, see: Reepmeyer et al. (1975 ▶); Zamora et al. (2003 ▶); Schmidt & Schieffer (2003 ▶); Mashkovskii (2005 ▶); Amini et al. (2007 ▶).

Experimental

Crystal data

C5H7Br2N2 +·Br−

M = 334.86

Monoclinic,

a = 5.5938 (3) Å

b = 11.2522 (6) Å

c = 14.4864 (9) Å

β = 104.571 (3)°

V = 882.48 (9) Å3

Z = 4

Mo Kα radiation

μ = 13.64 mm−1

T = 150 K

0.31 × 0.22 × 0.17 mm

Data collection

Bruker APEXII diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.058, T max = 0.098

7565 measured reflections

2032 independent reflections

1747 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.027

wR(F 2) = 0.060

S = 1.03

2032 reflections

94 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.86 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR2002 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and DIAMOND (Brandenburg & Berndt, 2001 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812015310/lh5448sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812015310/lh5448Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812015310/lh5448Isup3.cml

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

C5H7Br2N2+·Br−	F(000) = 624
Mr = 334.86	Dx = 2.52 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3086 reflections
a = 5.5938 (3) Å	θ = 2.9–27.5°
b = 11.2522 (6) Å	µ = 13.64 mm−1
c = 14.4864 (9) Å	T = 150 K
β = 104.571 (3)°	Prism, colourless
V = 882.48 (9) Å3	0.31 × 0.22 × 0.17 mm
Z = 4

Bruker APEXII diffractometer	1747 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.050
CCD rotation images, thin slices scans	θmax = 27.5°, θmin = 3.4°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −6→7
Tmin = 0.058, Tmax = 0.098	k = −14→12
7565 measured reflections	l = −18→17
2032 independent reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.027	H-atom parameters constrained
wR(F2) = 0.060	w = 1/[σ2(Fo2) + (0.0201P)2 + 0.142P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max = 0.002
2032 reflections	Δρmax = 0.63 e Å−3
94 parameters	Δρmin = −0.86 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0075 (4)

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
Br1	0.52217 (6)	0.60967 (3)	0.40218 (2)	0.01621 (11)
Br2	0.12689 (6)	0.86245 (3)	0.44145 (2)	0.01726 (11)
N2	0.7783 (5)	0.7167 (2)	0.57813 (19)	0.0142 (6)
N5	0.5520 (5)	0.8641 (3)	0.5998 (2)	0.0171 (6)
H5	0.4987	0.9266	0.6251	0.021*
C1	0.7626 (6)	0.8069 (3)	0.6365 (2)	0.0163 (7)
C3	0.5709 (6)	0.7178 (3)	0.5019 (2)	0.0141 (7)
C4	0.4301 (6)	0.8096 (3)	0.5154 (2)	0.0140 (7)
C6	0.9445 (7)	0.8397 (3)	0.7253 (2)	0.0222 (8)
H6A	0.9879	0.7706	0.7647	0.033*
H6B	0.8745	0.8986	0.7587	0.033*
H6C	1.0896	0.8713	0.7103	0.033*
C7	0.9765 (7)	0.6294 (3)	0.5945 (3)	0.0214 (8)
H7A	1.1062	0.6531	0.6483	0.032*
H7B	1.0403	0.6242	0.5390	0.032*
H7C	0.9137	0.5532	0.6069	0.032*
Br3	0.58756 (6)	0.58078 (3)	0.77871 (2)	0.01713 (12)

	U11	U22	U33	U12	U13	U23
Br1	0.0170 (2)	0.01589 (19)	0.01515 (19)	0.00097 (14)	0.00295 (14)	−0.00101 (12)
Br2	0.01324 (19)	0.0185 (2)	0.01989 (19)	0.00293 (14)	0.00389 (14)	0.00221 (13)
N2	0.0086 (14)	0.0175 (15)	0.0156 (14)	−0.0021 (12)	0.0013 (11)	0.0037 (11)
N5	0.0193 (16)	0.0141 (15)	0.0185 (15)	−0.0040 (12)	0.0060 (12)	−0.0026 (11)
C1	0.0153 (18)	0.0171 (18)	0.0162 (17)	−0.0055 (14)	0.0031 (14)	0.0020 (14)
C3	0.0124 (17)	0.0172 (17)	0.0123 (16)	−0.0017 (14)	0.0022 (13)	0.0011 (13)
C4	0.0107 (17)	0.0173 (18)	0.0138 (16)	−0.0015 (14)	0.0029 (13)	−0.0020 (13)
C6	0.021 (2)	0.025 (2)	0.0182 (18)	−0.0087 (16)	0.0008 (15)	−0.0019 (15)
C7	0.0156 (19)	0.023 (2)	0.024 (2)	0.0058 (15)	0.0019 (16)	0.0075 (14)
Br3	0.0163 (2)	0.0161 (2)	0.01874 (19)	−0.00155 (13)	0.00405 (14)	−0.00052 (13)

Br1—C3	1.855 (3)	C1—C6	1.472 (5)
Br2—C4	1.861 (3)	C3—C4	1.343 (5)
N2—C1	1.338 (4)	C6—H6A	0.9600
N2—C3	1.386 (4)	C6—H6B	0.9600
N2—C7	1.456 (4)	C6—H6C	0.9600
N5—C1	1.329 (4)	C7—H7A	0.9600
N5—C4	1.385 (4)	C7—H7B	0.9600
N5—H5	0.8800	C7—H7C	0.9600
C1—N2—C3	108.8 (3)	N5—C4—Br2	122.8 (2)
C1—N2—C7	125.3 (3)	C1—C6—H6A	109.5
C3—N2—C7	125.9 (3)	C1—C6—H6B	109.5
C1—N5—C4	109.2 (3)	H6A—C6—H6B	109.5
C1—N5—H5	125.4	C1—C6—H6C	109.5
C4—N5—H5	125.4	H6A—C6—H6C	109.5
N5—C1—N2	107.9 (3)	H6B—C6—H6C	109.5
N5—C1—C6	125.2 (3)	N2—C7—H7A	109.5
N2—C1—C6	127.0 (3)	N2—C7—H7B	109.5
C4—C3—N2	107.1 (3)	H7A—C7—H7B	109.5
C4—C3—Br1	129.9 (2)	N2—C7—H7C	109.5
N2—C3—Br1	123.0 (2)	H7A—C7—H7C	109.5
C3—C4—N5	107.0 (3)	H7B—C7—H7C	109.5
C3—C4—Br2	130.2 (2)
C4—N5—C1—N2	−0.3 (4)	C1—N2—C3—Br1	178.4 (2)
C4—N5—C1—C6	179.1 (3)	C7—N2—C3—Br1	−3.8 (5)
C3—N2—C1—N5	0.4 (4)	N2—C3—C4—N5	0.0 (4)
C7—N2—C1—N5	−177.4 (3)	Br1—C3—C4—N5	−178.5 (2)
C3—N2—C1—C6	−179.0 (3)	N2—C3—C4—Br2	−179.7 (2)
C7—N2—C1—C6	3.2 (5)	Br1—C3—C4—Br2	1.7 (5)
C1—N2—C3—C4	−0.2 (4)	C1—N5—C4—C3	0.2 (4)
C7—N2—C3—C4	177.5 (3)	C1—N5—C4—Br2	180.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···Br3i	0.88	2.35	3.216 (3)	168
C6—H6A···Br2ii	0.96	2.90	3.796 (3)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯Br3i	0.88	2.35	3.216 (3)	168
C6—H6A⋯Br2ii	0.96	2.90	3.796 (3)	156

Symmetry codes: (i) ; (ii) .