1,3-Bis(2-cyano-benz-yl)imidazolium bromide.

In the title salt, C(19)H(15)N(4) (+)·Br(-), the central imidazole ring makes dihedral angles of 83.1 (2) and 87.6 (2)° with the terminal benzene rings. The dihedral angle between the terminal benzene rings is 6.77 (19)°; the cyanide substituents have an anti orientation. In the crystal, the cations and anions are linked via C-H⋯N and C-H⋯Br hydrogen bonds, forming sheets lying parallel to the ac plane.

Related literature

For details and applications of N-heterocylic carbene, see: Wanzlick & Kleiner (1961 ▶); Fahlbusch et al. (2009 ▶); Demir et al. (2009 ▶); Grasa et al. (2002 ▶); Buchowicz et al. (2006 ▶); Marko et al. (2002 ▶).

Experimental

Crystal data

C19H15N4 +·Br−

M = 379.26

Monoclinic,

a = 9.0661 (9) Å

b = 8.0357 (9) Å

c = 24.697 (3) Å

β = 95.651 (2)°

V = 1790.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 2.30 mm−1

T = 296 K

0.36 × 0.17 × 0.10 mm

Data collection

Bruker APEXII DUO CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.494, T max = 0.799

12922 measured reflections

4066 independent reflections

2486 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.149

S = 1.02

4066 reflections

217 parameters

H-atom parameters constrained

Δρmax = 1.14 e Å−3

Δρmin = −0.82 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811048951/hb6514sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048951/hb6514Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811048951/hb6514Isup3.cml

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

C19H15N4+·Br−	F(000) = 768
Mr = 379.26	Dx = 1.407 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2803 reflections
a = 9.0661 (9) Å	θ = 2.9–23.8°
b = 8.0357 (9) Å	µ = 2.30 mm−1
c = 24.697 (3) Å	T = 296 K
β = 95.651 (2)°	Block, colourless
V = 1790.5 (3) Å3	0.36 × 0.17 × 0.10 mm
Z = 4

Bruker APEXII DUO CCD diffractometer	4066 independent reflections
Radiation source: fine-focus sealed tube	2486 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 27.5°, θmin = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.494, Tmax = 0.799	k = −10→10
12922 measured reflections	l = −32→32

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.149	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0749P)2 + 0.6395P] where P = (Fo2 + 2Fc2)/3
4066 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 1.14 e Å−3
0 restraints	Δρmin = −0.82 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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	0.29310 (4)	0.46183 (7)	0.271846 (19)	0.0744 (2)
N1	0.3270 (3)	0.0222 (4)	0.29878 (11)	0.0487 (7)
N2	0.1865 (3)	−0.0421 (4)	0.22727 (11)	0.0521 (8)
N3	0.6850 (4)	0.2721 (5)	0.43842 (14)	0.0763 (11)
N4	−0.1238 (5)	−0.2711 (6)	0.07253 (15)	0.0977 (15)
C1	0.3264 (4)	−0.0178 (5)	0.24721 (13)	0.0482 (8)
H1A	0.4092	−0.0274	0.2280	0.058*
C2	0.0970 (4)	−0.0140 (6)	0.26727 (16)	0.0659 (11)
H2A	−0.0058	−0.0215	0.2643	0.079*
C3	0.1858 (4)	0.0268 (6)	0.31198 (15)	0.0628 (11)
H3A	0.1557	0.0534	0.3459	0.075*
C4	0.4592 (4)	0.0639 (5)	0.33548 (14)	0.0570 (10)
H4A	0.4438	0.1698	0.3529	0.068*
H4B	0.5435	0.0756	0.3144	0.068*
C5	0.4932 (4)	−0.0676 (5)	0.37865 (13)	0.0467 (8)
C6	0.5839 (4)	−0.0257 (5)	0.42592 (13)	0.0466 (8)
C7	0.6238 (4)	−0.1459 (6)	0.46540 (14)	0.0605 (10)
H7A	0.6816	−0.1167	0.4972	0.073*
C8	0.5779 (5)	−0.3068 (6)	0.45731 (17)	0.0709 (12)
H8A	0.6076	−0.3878	0.4830	0.085*
C9	0.4881 (5)	−0.3487 (6)	0.41142 (19)	0.0741 (12)
H9A	0.4544	−0.4575	0.4067	0.089*
C10	0.4474 (5)	−0.2307 (6)	0.37226 (16)	0.0657 (11)
H10A	0.3881	−0.2616	0.3410	0.079*
C11	0.1370 (5)	−0.0897 (6)	0.17153 (16)	0.0749 (13)
H11A	0.0594	−0.1727	0.1720	0.090*
H11B	0.2191	−0.1401	0.1552	0.090*
C12	0.0786 (4)	0.0566 (5)	0.13661 (13)	0.0507 (9)
C13	0.1252 (4)	0.2175 (5)	0.14572 (15)	0.0579 (10)
H13A	0.1924	0.2412	0.1756	0.070*
C14	0.0744 (5)	0.3443 (6)	0.11149 (17)	0.0676 (11)
H14A	0.1077	0.4524	0.1183	0.081*
C15	−0.0260 (5)	0.3115 (6)	0.06708 (17)	0.0740 (12)
H15A	−0.0618	0.3978	0.0444	0.089*
C16	−0.0729 (5)	0.1509 (6)	0.05649 (16)	0.0693 (12)
H16A	−0.1383	0.1278	0.0260	0.083*
C17	−0.0230 (4)	0.0254 (5)	0.09104 (13)	0.0524 (9)
C18	0.6389 (4)	0.1393 (6)	0.43334 (13)	0.0540 (9)
C19	−0.0785 (5)	−0.1402 (6)	0.08064 (14)	0.0674 (12)

	U11	U22	U33	U12	U13	U23
Br1	0.0396 (2)	0.0842 (4)	0.0975 (4)	−0.00728 (19)	−0.00305 (18)	−0.0309 (2)
N1	0.0396 (14)	0.062 (2)	0.0417 (14)	−0.0013 (13)	−0.0096 (11)	−0.0008 (13)
N2	0.0481 (16)	0.054 (2)	0.0491 (15)	0.0021 (14)	−0.0196 (13)	−0.0085 (13)
N3	0.092 (3)	0.064 (3)	0.068 (2)	−0.018 (2)	−0.0216 (18)	−0.0005 (19)
N4	0.145 (4)	0.074 (3)	0.063 (2)	−0.033 (3)	−0.044 (2)	0.004 (2)
C1	0.0362 (15)	0.062 (3)	0.0448 (17)	0.0039 (15)	−0.0063 (13)	−0.0014 (16)
C2	0.0366 (17)	0.087 (3)	0.073 (2)	−0.0036 (18)	−0.0027 (16)	0.001 (2)
C3	0.054 (2)	0.083 (3)	0.0516 (19)	−0.003 (2)	0.0099 (16)	−0.001 (2)
C4	0.058 (2)	0.056 (3)	0.0509 (19)	−0.0101 (18)	−0.0213 (16)	−0.0008 (17)
C5	0.0467 (17)	0.045 (2)	0.0457 (17)	0.0022 (15)	−0.0080 (13)	−0.0016 (15)
C6	0.0464 (17)	0.052 (2)	0.0402 (16)	0.0005 (16)	−0.0039 (13)	−0.0024 (15)
C7	0.063 (2)	0.071 (3)	0.0456 (19)	0.000 (2)	−0.0081 (15)	0.0106 (18)
C8	0.075 (3)	0.065 (3)	0.071 (3)	0.008 (2)	−0.003 (2)	0.025 (2)
C9	0.083 (3)	0.042 (3)	0.095 (3)	−0.009 (2)	−0.004 (2)	0.005 (2)
C10	0.074 (3)	0.055 (3)	0.063 (2)	−0.002 (2)	−0.0172 (19)	−0.007 (2)
C11	0.095 (3)	0.058 (3)	0.062 (2)	0.010 (2)	−0.037 (2)	−0.014 (2)
C12	0.0511 (18)	0.052 (3)	0.0458 (17)	0.0003 (17)	−0.0088 (14)	−0.0069 (16)
C13	0.053 (2)	0.055 (3)	0.064 (2)	−0.0027 (18)	−0.0027 (16)	−0.009 (2)
C14	0.078 (3)	0.049 (3)	0.078 (3)	−0.007 (2)	0.022 (2)	−0.007 (2)
C15	0.095 (3)	0.063 (3)	0.065 (2)	0.017 (3)	0.008 (2)	0.014 (2)
C16	0.082 (3)	0.069 (3)	0.053 (2)	0.000 (2)	−0.0129 (19)	0.009 (2)
C17	0.059 (2)	0.054 (2)	0.0423 (17)	0.0001 (18)	−0.0079 (14)	0.0008 (16)
C18	0.058 (2)	0.059 (3)	0.0417 (17)	−0.0030 (19)	−0.0140 (15)	0.0000 (17)
C19	0.090 (3)	0.060 (3)	0.045 (2)	−0.006 (2)	−0.0303 (19)	0.0019 (19)

N1—C1	1.313 (4)	C7—H7A	0.9300
N1—C3	1.352 (5)	C8—C9	1.371 (6)
N1—C4	1.469 (4)	C8—H8A	0.9300
N2—C1	1.329 (4)	C9—C10	1.378 (6)
N2—C2	1.358 (5)	C9—H9A	0.9300
N2—C11	1.456 (4)	C10—H10A	0.9300
N3—C18	1.148 (5)	C11—C12	1.522 (6)
N4—C19	1.140 (6)	C11—H11A	0.9700
C1—H1A	0.9300	C11—H11B	0.9700
C2—C3	1.341 (5)	C12—C13	1.372 (5)
C2—H2A	0.9300	C12—C17	1.405 (4)
C3—H3A	0.9300	C13—C14	1.374 (6)
C4—C5	1.511 (5)	C13—H13A	0.9300
C4—H4A	0.9700	C14—C15	1.380 (6)
C4—H4B	0.9700	C14—H14A	0.9300
C5—C10	1.380 (6)	C15—C16	1.376 (7)
C5—C6	1.401 (4)	C15—H15A	0.9300
C6—C7	1.395 (5)	C16—C17	1.369 (5)
C6—C18	1.422 (6)	C16—H16A	0.9300
C7—C8	1.366 (6)	C17—C19	1.437 (6)
C1—N1—C3	109.1 (3)	C8—C9—C10	120.5 (4)
C1—N1—C4	125.4 (3)	C8—C9—H9A	119.8
C3—N1—C4	125.4 (3)	C10—C9—H9A	119.8
C1—N2—C2	108.8 (3)	C9—C10—C5	121.1 (3)
C1—N2—C11	125.7 (3)	C9—C10—H10A	119.5
C2—N2—C11	125.5 (3)	C5—C10—H10A	119.5
N1—C1—N2	107.9 (3)	N2—C11—C12	113.0 (3)
N1—C1—H1A	126.0	N2—C11—H11A	109.0
N2—C1—H1A	126.0	C12—C11—H11A	109.0
C3—C2—N2	106.7 (3)	N2—C11—H11B	109.0
C3—C2—H2A	126.7	C12—C11—H11B	109.0
N2—C2—H2A	126.7	H11A—C11—H11B	107.8
C2—C3—N1	107.5 (3)	C13—C12—C17	117.8 (3)
C2—C3—H3A	126.3	C13—C12—C11	123.4 (3)
N1—C3—H3A	126.3	C17—C12—C11	118.7 (3)
N1—C4—C5	111.9 (3)	C12—C13—C14	121.2 (3)
N1—C4—H4A	109.2	C12—C13—H13A	119.4
C5—C4—H4A	109.2	C14—C13—H13A	119.4
N1—C4—H4B	109.2	C13—C14—C15	120.2 (4)
C5—C4—H4B	109.2	C13—C14—H14A	119.9
H4A—C4—H4B	107.9	C15—C14—H14A	119.9
C10—C5—C6	118.0 (3)	C16—C15—C14	119.8 (4)
C10—C5—C4	123.0 (3)	C16—C15—H15A	120.1
C6—C5—C4	118.8 (3)	C14—C15—H15A	120.1
C7—C6—C5	120.5 (4)	C17—C16—C15	119.7 (4)
C7—C6—C18	119.4 (3)	C17—C16—H16A	120.1
C5—C6—C18	120.1 (3)	C15—C16—H16A	120.1
C8—C7—C6	119.9 (3)	C16—C17—C12	121.2 (4)
C8—C7—H7A	120.1	C16—C17—C19	118.9 (3)
C6—C7—H7A	120.1	C12—C17—C19	119.9 (3)
C7—C8—C9	120.1 (4)	N3—C18—C6	178.6 (4)
C7—C8—H8A	120.0	N4—C19—C17	179.3 (6)
C9—C8—H8A	120.0
C3—N1—C1—N2	−1.2 (4)	C7—C8—C9—C10	2.2 (7)
C4—N1—C1—N2	−178.2 (3)	C8—C9—C10—C5	−1.3 (7)
C2—N2—C1—N1	1.0 (4)	C6—C5—C10—C9	0.7 (6)
C11—N2—C1—N1	−179.5 (4)	C4—C5—C10—C9	176.2 (4)
C1—N2—C2—C3	−0.4 (5)	C1—N2—C11—C12	−100.4 (5)
C11—N2—C2—C3	−179.9 (4)	C2—N2—C11—C12	79.0 (5)
N2—C2—C3—N1	−0.3 (5)	N2—C11—C12—C13	28.0 (6)
C1—N1—C3—C2	0.9 (5)	N2—C11—C12—C17	−155.2 (4)
C4—N1—C3—C2	177.9 (4)	C17—C12—C13—C14	0.0 (6)
C1—N1—C4—C5	−111.6 (4)	C11—C12—C13—C14	176.8 (4)
C3—N1—C4—C5	71.9 (5)	C12—C13—C14—C15	0.3 (6)
N1—C4—C5—C10	24.2 (5)	C13—C14—C15—C16	−1.3 (7)
N1—C4—C5—C6	−160.3 (3)	C14—C15—C16—C17	1.9 (7)
C10—C5—C6—C7	−1.0 (5)	C15—C16—C17—C12	−1.6 (6)
C4—C5—C6—C7	−176.7 (3)	C15—C16—C17—C19	177.2 (4)
C10—C5—C6—C18	177.4 (4)	C13—C12—C17—C16	0.6 (6)
C4—C5—C6—C18	1.7 (5)	C11—C12—C17—C16	−176.3 (4)
C5—C6—C7—C8	1.9 (6)	C13—C12—C17—C19	−178.2 (4)
C18—C6—C7—C8	−176.5 (4)	C11—C12—C17—C19	4.9 (6)
C6—C7—C8—C9	−2.5 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···Br1i	0.93	2.70	3.531 (4)	149
C2—H2A···Br1ii	0.93	2.67	3.579 (4)	165
C3—H3A···N4iii	0.93	2.50	3.377 (6)	157
C4—H4B···Br1i	0.97	2.86	3.730 (4)	149
C7—H7A···N4iv	0.93	2.60	3.390 (5)	144
C10—H10A···Br1v	0.93	2.88	3.678 (4)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯Br1i	0.93	2.70	3.531 (4)	149
C2—H2A⋯Br1ii	0.93	2.67	3.579 (4)	165
C3—H3A⋯N4iii	0.93	2.50	3.377 (6)	157
C4—H4B⋯Br1i	0.97	2.86	3.730 (4)	149
C7—H7A⋯N4iv	0.93	2.60	3.390 (5)	144
C10—H10A⋯Br1v	0.93	2.88	3.678 (4)	144

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .