1-[6-(Hydroxy-meth-yl)-2-pyrid-yl]-3-(2,4,6-trimethyl-benz-yl)-1H-imidazol-3-ium bromide.

In the title compound, C(19)H(22)N(3)O(+)·Br(-), the imidazole ring is approximately coplanar with the pyridine ring [dihedral angle = 0.88 (13)°] and nearly perpendicular to the benzene ring [dihedral angle = 81.70 (13)°]. O-H⋯Br and C-H⋯Br hydrogen bonding helps to stabilize the crystal structure.

Related literature

For general background, see: Liddle et al. (2007 ▶); Ren et al. (2007 ▶); Arnold & Wilson (2007 ▶); Chianese & Crabtree (2005 ▶); Dyson et al. (2008 ▶); Patel et al. (2006 ▶). For synthesis, see: Hosseinzadeh et al. (2006 ▶).

Experimental

Crystal data

C19H22N3O+·Br−

M = 388.31

Monoclinic,

a = 11.2315 (3) Å

b = 11.5390 (3) Å

c = 14.3673 (4) Å

β = 100.833 (2)°

V = 1828.82 (9) Å3

Z = 4

Mo Kα radiation

μ = 2.26 mm−1

T = 296 (2) K

0.50 × 0.48 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.320, T max = 0.405

13818 measured reflections

4184 independent reflections

2287 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.116

S = 1.01

4184 reflections

220 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.60 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: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034764/xu2459sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034764/xu2459Isup2.hkl

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

C19H22N3O+·Br−	F(000) = 800
Mr = 388.31	Dx = 1.410 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3980 reflections
a = 11.2315 (3) Å	θ = 2.8–26.7°
b = 11.5390 (3) Å	µ = 2.26 mm−1
c = 14.3673 (4) Å	T = 296 K
β = 100.833 (2)°	Block, colourless
V = 1828.82 (9) Å3	0.50 × 0.48 × 0.40 mm
Z = 4

Bruker SAMRT CCD area-detector diffractometer	4184 independent reflections
Radiation source: fine-focus sealed tube	2287 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.320, Tmax = 0.405	k = −13→14
13818 measured reflections	l = −17→18

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.05P)2 + 0.57P] where P = (Fo2 + 2Fc2)/3
4184 reflections	(Δ/σ)max < 0.001
220 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

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	−0.28302 (3)	0.00291 (3)	−0.05646 (2)	0.05606 (10)
O1	−0.21350 (16)	0.2315 (2)	0.07160 (15)	0.0662 (7)
H1A	−0.2478	0.1920	0.0271	0.099*
N1	0.09397 (17)	0.27426 (17)	0.18365 (14)	0.0321 (5)
N2	0.28135 (17)	0.30337 (16)	0.27893 (14)	0.0305 (5)
N3	0.44633 (17)	0.20953 (17)	0.27441 (14)	0.0334 (5)
C1	0.1546 (2)	0.3348 (2)	0.25443 (17)	0.0316 (6)
C2	0.1075 (2)	0.4190 (2)	0.3045 (2)	0.0445 (8)
H2A	0.1547	0.4574	0.3553	0.053*
C3	−0.0135 (3)	0.4434 (3)	0.2752 (2)	0.0531 (9)
H3A	−0.0507	0.4989	0.3068	0.064*
C4	−0.0795 (2)	0.3852 (2)	0.1986 (2)	0.0444 (8)
H4A	−0.1606	0.4034	0.1764	0.053*
C5	−0.0234 (2)	0.2998 (2)	0.15572 (18)	0.0356 (7)
C6	−0.0886 (2)	0.2276 (2)	0.0752 (2)	0.0445 (8)
H6A	−0.0703	0.2563	0.0160	0.053*
H6B	−0.0608	0.1480	0.0832	0.053*
C7	0.3316 (2)	0.2205 (2)	0.23424 (18)	0.0346 (6)
H7A	0.2919	0.1775	0.1830	0.042*
C8	0.3694 (2)	0.3481 (2)	0.34984 (18)	0.0380 (7)
H8A	0.3598	0.4075	0.3916	0.046*
C9	0.4719 (2)	0.2892 (2)	0.34690 (18)	0.0384 (7)
H9A	0.5466	0.3002	0.3866	0.046*
C10	0.5327 (2)	0.1277 (2)	0.24373 (18)	0.0376 (7)
H10A	0.5877	0.1707	0.2121	0.045*
H10B	0.4880	0.0740	0.1982	0.045*
C11	0.6055 (2)	0.0601 (2)	0.32432 (17)	0.0312 (6)
C12	0.7292 (2)	0.0816 (2)	0.35423 (17)	0.0320 (6)
C13	0.7950 (2)	0.0118 (2)	0.42336 (17)	0.0339 (6)
H13A	0.8775	0.0261	0.4427	0.041*
C14	0.7435 (2)	−0.0781 (2)	0.46487 (18)	0.0368 (7)
C15	0.6197 (2)	−0.0969 (2)	0.43645 (18)	0.0370 (7)
H15A	0.5830	−0.1563	0.4645	0.044*
C16	0.5498 (2)	−0.0293 (2)	0.36734 (18)	0.0336 (7)
C17	0.4158 (2)	−0.0533 (3)	0.3403 (2)	0.0470 (8)
H17A	0.3971	−0.1241	0.3696	0.070*
H17B	0.3935	−0.0604	0.2727	0.070*
H17C	0.3713	0.0094	0.3615	0.070*
C18	0.7936 (2)	0.1776 (2)	0.3128 (2)	0.0466 (8)
H18A	0.8792	0.1721	0.3367	0.070*
H18B	0.7643	0.2511	0.3303	0.070*
H18C	0.7783	0.1708	0.2450	0.070*
C19	0.8180 (3)	−0.1551 (3)	0.5387 (2)	0.0521 (8)
H19A	0.9026	−0.1385	0.5423	0.078*
H19B	0.8026	−0.2348	0.5215	0.078*
H19C	0.7963	−0.1408	0.5992	0.078*

	U11	U22	U33	U12	U13	U23
Br1	0.0685 (2)	0.04819 (17)	0.04329 (16)	−0.00279 (17)	−0.01057 (14)	−0.00348 (15)
O1	0.0395 (11)	0.0820 (15)	0.0724 (15)	−0.0069 (11)	−0.0020 (11)	−0.0294 (12)
N1	0.0311 (11)	0.0305 (11)	0.0330 (12)	−0.0008 (9)	0.0022 (9)	0.0017 (9)
N2	0.0304 (11)	0.0302 (11)	0.0296 (11)	0.0007 (9)	0.0021 (9)	0.0001 (9)
N3	0.0290 (11)	0.0338 (11)	0.0346 (12)	0.0002 (9)	−0.0014 (9)	0.0000 (9)
C1	0.0312 (13)	0.0309 (13)	0.0324 (14)	0.0006 (11)	0.0049 (11)	0.0053 (11)
C2	0.0388 (15)	0.0424 (15)	0.0495 (17)	0.0016 (13)	0.0011 (13)	−0.0122 (13)
C3	0.0433 (17)	0.0473 (16)	0.068 (2)	0.0062 (14)	0.0089 (15)	−0.0158 (16)
C4	0.0314 (14)	0.0379 (15)	0.0611 (19)	0.0021 (12)	0.0015 (13)	−0.0063 (14)
C5	0.0373 (14)	0.0316 (13)	0.0365 (15)	−0.0057 (11)	0.0031 (12)	0.0074 (11)
C6	0.0367 (15)	0.0509 (17)	0.0420 (16)	−0.0047 (13)	−0.0029 (13)	−0.0032 (14)
C7	0.0336 (14)	0.0359 (14)	0.0319 (14)	−0.0010 (12)	−0.0001 (11)	−0.0012 (12)
C8	0.0393 (14)	0.0377 (14)	0.0341 (15)	−0.0042 (12)	0.0000 (12)	−0.0040 (12)
C9	0.0355 (14)	0.0402 (15)	0.0360 (15)	−0.0055 (12)	−0.0023 (12)	−0.0051 (12)
C10	0.0335 (14)	0.0437 (15)	0.0342 (15)	0.0039 (12)	0.0030 (12)	−0.0027 (12)
C11	0.0303 (13)	0.0309 (13)	0.0317 (14)	0.0014 (11)	0.0042 (11)	−0.0022 (11)
C12	0.0311 (13)	0.0320 (13)	0.0336 (14)	−0.0019 (11)	0.0077 (11)	−0.0022 (11)
C13	0.0246 (12)	0.0404 (15)	0.0356 (13)	−0.0004 (12)	0.0031 (10)	−0.0022 (12)
C14	0.0416 (15)	0.0386 (14)	0.0306 (14)	0.0082 (12)	0.0073 (12)	0.0002 (12)
C15	0.0408 (14)	0.0341 (14)	0.0383 (15)	−0.0060 (12)	0.0131 (12)	0.0037 (12)
C16	0.0325 (13)	0.0332 (14)	0.0359 (14)	−0.0008 (11)	0.0087 (11)	−0.0080 (11)
C17	0.0353 (15)	0.0474 (16)	0.0582 (19)	−0.0060 (13)	0.0088 (14)	−0.0031 (15)
C18	0.0364 (15)	0.0491 (17)	0.0519 (18)	−0.0067 (13)	0.0018 (13)	0.0090 (14)
C19	0.0507 (17)	0.0587 (18)	0.0465 (18)	0.0092 (15)	0.0079 (14)	0.0163 (15)

O1—C6	1.394 (3)	C10—C11	1.504 (3)
O1—H1A	0.8200	C10—H10A	0.9700
N1—C1	1.314 (3)	C10—H10B	0.9700
N1—C5	1.336 (3)	C11—C12	1.398 (3)
N2—C7	1.335 (3)	C11—C16	1.408 (4)
N2—C8	1.380 (3)	C12—C13	1.380 (3)
N2—C1	1.447 (3)	C12—C18	1.505 (4)
N3—C7	1.315 (3)	C13—C14	1.377 (4)
N3—C9	1.378 (3)	C13—H13A	0.9300
N3—C10	1.479 (3)	C14—C15	1.390 (3)
C1—C2	1.372 (4)	C14—C19	1.510 (4)
C2—C3	1.373 (4)	C15—C16	1.385 (3)
C2—H2A	0.9300	C15—H15A	0.9300
C3—C4	1.380 (4)	C16—C17	1.509 (3)
C3—H3A	0.9300	C17—H17A	0.9600
C4—C5	1.377 (4)	C17—H17B	0.9600
C4—H4A	0.9300	C17—H17C	0.9600
C5—C6	1.500 (3)	C18—H18A	0.9600
C6—H6A	0.9700	C18—H18B	0.9600
C6—H6B	0.9700	C18—H18C	0.9600
C7—H7A	0.9300	C19—H19A	0.9600
C8—C9	1.344 (3)	C19—H19B	0.9600
C8—H8A	0.9300	C19—H19C	0.9600
C9—H9A	0.9300
C6—O1—H1A	109.5	C11—C10—H10A	108.9
C1—N1—C5	117.0 (2)	N3—C10—H10B	108.9
C7—N2—C8	108.3 (2)	C11—C10—H10B	108.9
C7—N2—C1	123.3 (2)	H10A—C10—H10B	107.8
C8—N2—C1	128.4 (2)	C12—C11—C16	119.5 (2)
C7—N3—C9	108.4 (2)	C12—C11—C10	120.7 (2)
C7—N3—C10	125.0 (2)	C16—C11—C10	119.8 (2)
C9—N3—C10	126.6 (2)	C13—C12—C11	119.0 (2)
N1—C1—C2	126.0 (2)	C13—C12—C18	118.8 (2)
N1—C1—N2	113.4 (2)	C11—C12—C18	122.2 (2)
C2—C1—N2	120.6 (2)	C14—C13—C12	122.6 (2)
C1—C2—C3	116.2 (2)	C14—C13—H13A	118.7
C1—C2—H2A	121.9	C12—C13—H13A	118.7
C3—C2—H2A	121.9	C13—C14—C15	117.9 (2)
C2—C3—C4	119.8 (3)	C13—C14—C19	121.6 (2)
C2—C3—H3A	120.1	C15—C14—C19	120.4 (2)
C4—C3—H3A	120.1	C16—C15—C14	121.5 (2)
C5—C4—C3	118.8 (3)	C16—C15—H15A	119.2
C5—C4—H4A	120.6	C14—C15—H15A	119.2
C3—C4—H4A	120.6	C15—C16—C11	119.3 (2)
N1—C5—C4	122.1 (2)	C15—C16—C17	119.0 (2)
N1—C5—C6	114.9 (2)	C11—C16—C17	121.7 (2)
C4—C5—C6	123.0 (2)	C16—C17—H17A	109.5
O1—C6—C5	110.7 (2)	C16—C17—H17B	109.5
O1—C6—H6A	109.5	H17A—C17—H17B	109.5
C5—C6—H6A	109.5	C16—C17—H17C	109.5
O1—C6—H6B	109.5	H17A—C17—H17C	109.5
C5—C6—H6B	109.5	H17B—C17—H17C	109.5
H6A—C6—H6B	108.1	C12—C18—H18A	109.5
N3—C7—N2	109.0 (2)	C12—C18—H18B	109.5
N3—C7—H7A	125.5	H18A—C18—H18B	109.5
N2—C7—H7A	125.5	C12—C18—H18C	109.5
C9—C8—N2	106.7 (2)	H18A—C18—H18C	109.5
C9—C8—H8A	126.7	H18B—C18—H18C	109.5
N2—C8—H8A	126.7	C14—C19—H19A	109.5
C8—C9—N3	107.6 (2)	C14—C19—H19B	109.5
C8—C9—H9A	126.2	H19A—C19—H19B	109.5
N3—C9—H9A	126.2	C14—C19—H19C	109.5
N3—C10—C11	113.2 (2)	H19A—C19—H19C	109.5
N3—C10—H10A	108.9	H19B—C19—H19C	109.5
C5—N1—C1—C2	2.5 (4)	C7—N3—C9—C8	0.4 (3)
C5—N1—C1—N2	−178.8 (2)	C10—N3—C9—C8	178.4 (2)
C7—N2—C1—N1	−0.3 (3)	C7—N3—C10—C11	−132.4 (2)
C8—N2—C1—N1	−179.0 (2)	C9—N3—C10—C11	49.8 (3)
C7—N2—C1—C2	178.5 (2)	N3—C10—C11—C12	−109.5 (3)
C8—N2—C1—C2	−0.2 (4)	N3—C10—C11—C16	73.4 (3)
N1—C1—C2—C3	−2.0 (4)	C16—C11—C12—C13	2.1 (4)
N2—C1—C2—C3	179.4 (2)	C10—C11—C12—C13	−175.0 (2)
C1—C2—C3—C4	−0.8 (4)	C16—C11—C12—C18	−178.5 (2)
C2—C3—C4—C5	2.8 (4)	C10—C11—C12—C18	4.4 (4)
C1—N1—C5—C4	−0.2 (4)	C11—C12—C13—C14	−0.5 (4)
C1—N1—C5—C6	−179.6 (2)	C18—C12—C13—C14	−179.8 (2)
C3—C4—C5—N1	−2.4 (4)	C12—C13—C14—C15	−1.2 (4)
C3—C4—C5—C6	177.0 (3)	C12—C13—C14—C19	178.5 (2)
N1—C5—C6—O1	160.1 (2)	C13—C14—C15—C16	1.2 (4)
C4—C5—C6—O1	−19.3 (4)	C19—C14—C15—C16	−178.5 (3)
C9—N3—C7—N2	−0.9 (3)	C14—C15—C16—C11	0.4 (4)
C10—N3—C7—N2	−179.0 (2)	C14—C15—C16—C17	−179.4 (2)
C8—N2—C7—N3	1.0 (3)	C12—C11—C16—C15	−2.1 (4)
C1—N2—C7—N3	−177.9 (2)	C10—C11—C16—C15	175.0 (2)
C7—N2—C8—C9	−0.8 (3)	C12—C11—C16—C17	177.7 (2)
C1—N2—C8—C9	178.1 (2)	C10—C11—C16—C17	−5.2 (4)
N2—C8—C9—N3	0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Br1	0.82	2.49	3.227 (2)	151
C7—H7A···Br1i	0.93	2.75	3.598 (2)	152
C8—H8A···Br1ii	0.93	2.89	3.745 (2)	154
C10—H10B···Br1i	0.97	2.91	3.813 (2)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯Br1	0.82	2.49	3.227 (2)	151
C7—H7A⋯Br1i	0.93	2.75	3.598 (2)	152
C8—H8A⋯Br1ii	0.93	2.89	3.745 (2)	154
C10—H10B⋯Br1i	0.97	2.91	3.813 (2)	155

Symmetry codes: (i) ; (ii) .