1,3-Bis[(6-methyl-2-pyrid-yl)meth-yl]imidazolium bromide.

The title compound, C(17)H(19)N(4) (+)·Br(-), is built up from 1,3-bis-[(6-methyl-2-pyridin-yl)meth-yl]imidazolium cations and bromide anions. Each of two 6-methyl-2-pyridyl rings is rotated out of the imidazole plane, making dihedral angles of 79.90 (9) and 86.40 (9)°. The packing is consolidated by aromatic π-π inter-actions between the pyridine rings of neighbouring mol-ecules [centroid-centroid distance = 3.554 (2) Å] and by weak C-H⋯N and C-H⋯Br hydrogen bonds.

Related literature

For the synthesis of N-heterocyclic carbenes, see: Arduengo et al. (1991 ▶); Enders et al. (1996 ▶); Frenzel et al. (1999 ▶); Gardiner et al. (1999 ▶); Herrmann et al. (1998 ▶); McGuinness et al. (1998 ▶); Öfele (1968 ▶); Wanzlick & Schonherr (1968); Wanzlick & Schönherr (1968 ▶); Zhang & Trudell (2000 ▶). For related structures, see: Weskamp et al. (1999a ▶ b ▶).

Experimental

Crystal data

C17H19N4 +·Br−

M = 359.27

Monoclinic,

a = 8.2951 (4) Å

b = 12.4992 (5) Å

c = 16.1786 (7) Å

β = 95.709 (1)°

V = 1669.11 (13) Å3

Z = 4

Mo Kα radiation

μ = 2.47 mm−1

T = 173 K

0.40 × 0.25 × 0.15 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.439, T max = 0.709

10482 measured reflections

3923 independent reflections

2861 reflections with I > 2σ(I)

R int = 0.070

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.094

S = 1.00

3923 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.92 e Å−3

Δρmin = −0.50 e Å−3

Data collection: SMART (Bruker, 1997 ▶); cell refinement: SAINT (Bruker, 1997 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006710/lx2088sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006710/lx2088Isup2.hkl

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

C17H19N4+·Br−	F(000) = 736
Mr = 359.27	Dx = 1.430 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3923 reflections
a = 8.2951 (4) Å	θ = 2.1–28.3°
b = 12.4992 (5) Å	µ = 2.47 mm−1
c = 16.1786 (7) Å	T = 173 K
β = 95.709 (1)°	Block, yellow
V = 1669.11 (13) Å3	0.40 × 0.25 × 0.15 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	3923 independent reflections
Radiation source: fine-focus sealed tube	2861 reflections with I > 2σ(I)
graphite	Rint = 0.070
Detector resolution: 10.0 pixels mm-1	θmax = 28.3°, θmin = 2.1°
φ and ω scans	h = −10→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −8→16
Tmin = 0.439, Tmax = 0.709	l = −21→20
10482 measured reflections

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)] = 0.037	Hydrogen site location: difference Fourier map
wR(F2) = 0.094	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0442P)2] where P = (Fo2 + 2Fc2)/3
3923 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.92 e Å−3
0 restraints	Δρmin = −0.49 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Br	0.25933 (3)	−0.13979 (2)	0.728857 (17)	0.02867 (10)
N1	0.2300 (3)	0.43039 (18)	0.55743 (13)	0.0278 (5)
N2	0.1795 (3)	0.32251 (18)	0.69967 (13)	0.0249 (5)
N3	0.3401 (3)	0.18620 (18)	0.70972 (12)	0.0251 (5)
N4	0.6655 (3)	0.02641 (18)	0.63640 (13)	0.0278 (5)
C1	0.3308 (4)	0.4122 (3)	0.42228 (19)	0.0461 (8)
H1A	0.4447	0.3965	0.4401	0.069*
H1B	0.3231	0.4511	0.3695	0.069*
H1C	0.2699	0.3451	0.4151	0.069*
C2	0.2610 (3)	0.4796 (2)	0.48712 (16)	0.0316 (6)
C3	0.2275 (4)	0.5877 (2)	0.47302 (19)	0.0372 (7)
H3A	0.2493	0.6205	0.4223	0.045*
C4	0.1625 (4)	0.6461 (2)	0.5333 (2)	0.0405 (7)
H4A	0.1389	0.7199	0.5249	0.049*
C5	0.1314 (3)	0.5967 (2)	0.60658 (19)	0.0343 (7)
H5A	0.0881	0.6358	0.6496	0.041*
C6	0.1653 (3)	0.4883 (2)	0.61548 (16)	0.0268 (6)
C7	0.1255 (3)	0.4340 (2)	0.69380 (17)	0.0283 (6)
H7A	0.1770	0.4740	0.7422	0.034*
H7B	0.0068	0.4363	0.6963	0.034*
C8	0.0851 (3)	0.2329 (2)	0.68219 (17)	0.0297 (6)
H8A	−0.0289	0.2316	0.6684	0.036*
C9	0.1843 (3)	0.1478 (2)	0.68830 (17)	0.0302 (6)
H9A	0.1538	0.0750	0.6796	0.036*
C10	0.3325 (3)	0.2922 (2)	0.71530 (15)	0.0257 (6)
H10A	0.4222	0.3386	0.7283	0.031*
C11	0.4884 (3)	0.1223 (2)	0.71751 (17)	0.0280 (6)
H11A	0.4651	0.0515	0.7411	0.034*
H11B	0.5704	0.1582	0.7567	0.034*
C12	0.5575 (3)	0.1063 (2)	0.63500 (16)	0.0251 (6)
C13	0.5148 (3)	0.1686 (2)	0.56543 (16)	0.0298 (6)
H13A	0.4382	0.2250	0.5667	0.036*
C14	0.5875 (3)	0.1459 (2)	0.49366 (18)	0.0330 (6)
H14A	0.5608	0.1865	0.4446	0.040*
C15	0.6987 (3)	0.0642 (2)	0.49443 (17)	0.0331 (7)
H15A	0.7500	0.0480	0.4460	0.040*
C16	0.7350 (3)	0.0057 (2)	0.56687 (17)	0.0305 (6)
C17	0.8531 (4)	−0.0873 (3)	0.5706 (2)	0.0445 (8)
H17A	0.9412	−0.0744	0.6144	0.067*
H17B	0.8980	−0.0943	0.5170	0.067*
H17C	0.7964	−0.1535	0.5826	0.067*

	U11	U22	U33	U12	U13	U23
Br	0.02798 (15)	0.02717 (15)	0.03144 (16)	0.00081 (11)	0.00575 (11)	0.00151 (12)
N1	0.0321 (12)	0.0264 (12)	0.0249 (11)	−0.0012 (10)	0.0022 (10)	−0.0001 (9)
N2	0.0292 (12)	0.0238 (11)	0.0223 (11)	−0.0008 (9)	0.0057 (9)	−0.0003 (9)
N3	0.0275 (12)	0.0278 (12)	0.0205 (11)	0.0002 (10)	0.0043 (9)	0.0004 (9)
N4	0.0261 (12)	0.0312 (13)	0.0260 (11)	−0.0004 (10)	0.0014 (9)	−0.0010 (10)
C1	0.063 (2)	0.051 (2)	0.0266 (15)	0.0014 (17)	0.0125 (15)	0.0030 (14)
C2	0.0321 (15)	0.0388 (16)	0.0234 (13)	−0.0044 (13)	−0.0005 (11)	0.0019 (12)
C3	0.0381 (17)	0.0395 (18)	0.0332 (16)	−0.0073 (14)	−0.0008 (13)	0.0111 (14)
C4	0.0411 (17)	0.0278 (16)	0.052 (2)	0.0000 (13)	0.0002 (15)	0.0080 (14)
C5	0.0347 (16)	0.0268 (15)	0.0415 (17)	−0.0018 (13)	0.0035 (13)	−0.0015 (13)
C6	0.0234 (13)	0.0292 (15)	0.0273 (13)	−0.0039 (11)	−0.0008 (11)	−0.0005 (11)
C7	0.0329 (15)	0.0234 (14)	0.0290 (14)	0.0036 (11)	0.0057 (12)	−0.0016 (11)
C8	0.0279 (14)	0.0296 (15)	0.0318 (15)	−0.0043 (12)	0.0039 (12)	−0.0017 (12)
C9	0.0315 (14)	0.0280 (15)	0.0315 (14)	−0.0038 (12)	0.0052 (12)	−0.0033 (12)
C10	0.0315 (14)	0.0246 (14)	0.0211 (13)	−0.0041 (11)	0.0035 (11)	−0.0027 (10)
C11	0.0304 (14)	0.0296 (15)	0.0241 (13)	0.0062 (11)	0.0034 (11)	0.0028 (11)
C12	0.0241 (13)	0.0259 (13)	0.0251 (13)	−0.0039 (11)	0.0021 (11)	−0.0023 (11)
C13	0.0367 (16)	0.0260 (14)	0.0271 (14)	0.0015 (12)	0.0045 (12)	0.0020 (11)
C14	0.0381 (16)	0.0355 (16)	0.0258 (14)	−0.0051 (13)	0.0048 (12)	0.0055 (12)
C15	0.0308 (15)	0.0418 (17)	0.0283 (14)	−0.0083 (13)	0.0116 (12)	−0.0060 (13)
C16	0.0252 (14)	0.0361 (16)	0.0303 (14)	−0.0014 (12)	0.0023 (11)	−0.0053 (12)
C17	0.0432 (18)	0.053 (2)	0.0372 (17)	0.0125 (16)	0.0055 (14)	−0.0081 (15)

N1—C6	1.339 (3)	C6—C7	1.503 (4)
N1—C2	1.341 (3)	C7—H7A	0.9900
N2—C10	1.324 (3)	C7—H7B	0.9900
N2—C8	1.380 (3)	C8—C9	1.343 (4)
N2—C7	1.464 (3)	C8—H8A	0.9500
N3—C10	1.330 (3)	C9—H9A	0.9500
N3—C9	1.389 (3)	C10—H10A	0.9500
N3—C11	1.462 (3)	C11—C12	1.518 (4)
N4—C16	1.339 (3)	C11—H11A	0.9900
N4—C12	1.341 (3)	C11—H11B	0.9900
C1—C2	1.506 (4)	C12—C13	1.385 (4)
C1—H1A	0.9800	C13—C14	1.390 (4)
C1—H1B	0.9800	C13—H13A	0.9500
C1—H1C	0.9800	C14—C15	1.375 (4)
C2—C3	1.393 (4)	C14—H14A	0.9500
C3—C4	1.371 (5)	C15—C16	1.389 (4)
C3—H3A	0.9500	C15—H15A	0.9500
C4—C5	1.383 (4)	C16—C17	1.518 (4)
C4—H4A	0.9500	C17—H17A	0.9800
C5—C6	1.388 (4)	C17—H17B	0.9800
C5—H5A	0.9500	C17—H17C	0.9800
C6—N1—C2	118.1 (2)	C9—C8—H8A	126.4
C10—N2—C8	108.7 (2)	N2—C8—H8A	126.4
C10—N2—C7	124.5 (2)	C8—C9—N3	107.0 (2)
C8—N2—C7	126.5 (2)	C8—C9—H9A	126.5
C10—N3—C9	108.2 (2)	N3—C9—H9A	126.5
C10—N3—C11	125.7 (2)	N2—C10—N3	108.8 (2)
C9—N3—C11	125.9 (2)	N2—C10—H10A	125.6
C16—N4—C12	118.2 (2)	N3—C10—H10A	125.6
C2—C1—H1A	109.5	N3—C11—C12	112.6 (2)
C2—C1—H1B	109.5	N3—C11—H11A	109.1
H1A—C1—H1B	109.5	C12—C11—H11A	109.1
C2—C1—H1C	109.5	N3—C11—H11B	109.1
H1A—C1—H1C	109.5	C12—C11—H11B	109.1
H1B—C1—H1C	109.5	H11A—C11—H11B	107.8
N1—C2—C3	122.1 (3)	N4—C12—C13	123.3 (2)
N1—C2—C1	117.0 (3)	N4—C12—C11	113.2 (2)
C3—C2—C1	120.9 (3)	C13—C12—C11	123.5 (2)
C4—C3—C2	119.1 (3)	C12—C13—C14	117.8 (3)
C4—C3—H3A	120.5	C12—C13—H13A	121.1
C2—C3—H3A	120.5	C14—C13—H13A	121.1
C3—C4—C5	119.5 (3)	C15—C14—C13	119.4 (3)
C3—C4—H4A	120.3	C15—C14—H14A	120.3
C5—C4—H4A	120.3	C13—C14—H14A	120.3
C4—C5—C6	118.1 (3)	C14—C15—C16	119.2 (3)
C4—C5—H5A	120.9	C14—C15—H15A	120.4
C6—C5—H5A	120.9	C16—C15—H15A	120.4
N1—C6—C5	123.1 (3)	N4—C16—C15	122.1 (3)
N1—C6—C7	118.9 (2)	N4—C16—C17	116.4 (3)
C5—C6—C7	118.0 (2)	C15—C16—C17	121.4 (3)
N2—C7—C6	113.2 (2)	C16—C17—H17A	109.5
N2—C7—H7A	108.9	C16—C17—H17B	109.5
C6—C7—H7A	108.9	H17A—C17—H17B	109.5
N2—C7—H7B	108.9	C16—C17—H17C	109.5
C6—C7—H7B	108.9	H17A—C17—H17C	109.5
H7A—C7—H7B	107.8	H17B—C17—H17C	109.5
C9—C8—N2	107.3 (2)
C6—N1—C2—C3	−0.3 (4)	C8—N2—C10—N3	−0.9 (3)
C6—N1—C2—C1	−178.9 (3)	C7—N2—C10—N3	−175.1 (2)
N1—C2—C3—C4	0.8 (4)	C9—N3—C10—N2	0.9 (3)
C1—C2—C3—C4	179.4 (3)	C11—N3—C10—N2	175.9 (2)
C2—C3—C4—C5	−0.1 (4)	C10—N3—C11—C12	−89.3 (3)
C3—C4—C5—C6	−1.1 (4)	C9—N3—C11—C12	84.9 (3)
C2—N1—C6—C5	−1.0 (4)	C16—N4—C12—C13	−0.2 (4)
C2—N1—C6—C7	178.4 (2)	C16—N4—C12—C11	−179.6 (2)
C4—C5—C6—N1	1.7 (4)	N3—C11—C12—N4	−163.2 (2)
C4—C5—C6—C7	−177.7 (3)	N3—C11—C12—C13	17.3 (4)
C10—N2—C7—C6	73.2 (3)	N4—C12—C13—C14	0.4 (4)
C8—N2—C7—C6	−100.0 (3)	C11—C12—C13—C14	179.8 (3)
N1—C6—C7—N2	5.8 (3)	C12—C13—C14—C15	−0.5 (4)
C5—C6—C7—N2	−174.8 (2)	C13—C14—C15—C16	0.4 (4)
C10—N2—C8—C9	0.5 (3)	C12—N4—C16—C15	0.1 (4)
C7—N2—C8—C9	174.6 (2)	C12—N4—C16—C17	−178.4 (2)
N2—C8—C9—N3	0.1 (3)	C14—C15—C16—N4	−0.2 (4)
C10—N3—C9—C8	−0.6 (3)	C14—C15—C16—C17	178.2 (3)
C11—N3—C9—C8	−175.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N4i	0.99	2.34	3.308 (4)	165
C7—H7B···Brii	0.99	2.79	3.660 (3)	147
C9—H9A···Br	0.95	2.91	3.695 (3)	141
C10—H10A···Bri	0.95	2.68	3.521 (3)	148
C11—H11A···Br	0.99	2.93	3.801 (3)	147
C11—H11B···Bri	0.99	2.89	3.690 (3)	138

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯N4i	0.99	2.34	3.308 (4)	165
C7—H7B⋯Brii	0.99	2.79	3.660 (3)	147
C9—H9A⋯Br	0.95	2.91	3.695 (3)	141
C10—H10A⋯Bri	0.95	2.68	3.521 (3)	148
C11—H11A⋯Br	0.99	2.93	3.801 (3)	147
C11—H11B⋯Bri	0.99	2.89	3.690 (3)	138

Symmetry codes: (i) ; (ii) .