1-Methyl-4-(1-methyl-1H-benzimidazol-2-yl)pyridinium iodide.

The cation of the title compound, C(14)H(14)N(3) (+)·I(-), is non-planar, the dihedral angle between the benzimidazole and the 1-methyl-pyridinium planes being 37.4 (2)°. The crystal structure is stabilized by weak π-π stacking inter-actions, the centroid-centroid distances between 1-methyl-imidazole and benzimidazole planes being 3.678 (4) Å.

Related literature

For background to imidazole and its derivatives, see: Huang et al. (2004 ▶). For the biological activity of benzimidazole, see: Demirayak et al. (2002 ▶); Pawar et al. (2004 ▶).

Experimental

Crystal data

C14H14N3 +·I−

M = 351.18

Triclinic,

a = 7.7048 (15) Å

b = 9.9264 (18) Å

c = 10.1772 (19) Å

α = 64.888 (3)°

β = 72.933 (3)°

γ = 76.394 (4)°

V = 668.2 (2) Å3

Z = 2

Mo Kα radiation

μ = 2.38 mm−1

T = 291 K

0.35 × 0.25 × 0.05 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2000 ▶) T min = 0.493, T max = 0.887

3353 measured reflections

2307 independent reflections

1840 reflections with I > 2σ(I)

R int = 0.058

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.092

S = 1.00

2307 reflections

163 parameters

H-atom parameters constrained

Δρmax = 0.94 e Å−3

Δρmin = −0.48 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809053938/bx2252sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809053938/bx2252Isup2.hkl

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

C14H14N3+·I−	Z = 2
Mr = 351.18	F(000) = 344
Triclinic, P1	Dx = 1.745 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7048 (15) Å	Cell parameters from 1236 reflections
b = 9.9264 (18) Å	θ = 3.1–22.1°
c = 10.1772 (19) Å	µ = 2.38 mm−1
α = 64.888 (3)°	T = 291 K
β = 72.933 (3)°	Piece, colorless
γ = 76.394 (4)°	0.35 × 0.25 × 0.05 mm
V = 668.2 (2) Å3

Bruker SMART CCD area-detector diffractometer	2307 independent reflections
Radiation source: sealed tube	1840 reflections with I > 2σ(I)
graphite	Rint = 0.058
phi and ω scans	θmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)	h = −9→7
Tmin = 0.493, Tmax = 0.887	k = −10→11
3353 measured reflections	l = −12→12

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.092	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.0301P)2] where P = (Fo2 + 2Fc2)/3
2307 reflections	(Δ/σ)max < 0.001
163 parameters	Δρmax = 0.94 e Å−3
0 restraints	Δρmin = −0.48 e Å−3

Geometry. Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)7.5483 (0.0040) x + 0.9256 (0.0225) y + 1.1206 (0.0247) z = 6.5511 (0.0171)* 0.0017 (0.0039) N1 * 0.0018 (0.0041) C2 * -0.0063 (0.0040) C3 * 0.0074 (0.0040) C4 * -0.0041 (0.0042) C5 * -0.0004 (0.0041) C6Rms deviation of fitted atoms = 0.00446.8822 (0.0088) x + 3.4760 (0.0239) y + 7.0324 (0.0184) z = 8.6547 (0.0229)Angle to previous plane (with approximate e.s.d.) = 37.43 (0.15)* -0.0020 (0.0031) C7 * -0.0067 (0.0031) N2 * 0.0128 (0.0031) C8 * -0.0138 (0.0030) C13 * 0.0098 (0.0030) N3Rms deviation of fitted atoms = 0.0100

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
C1	0.7976 (9)	0.1720 (7)	0.3724 (7)	0.0574 (18)
H1A	0.7850	0.1418	0.4774	0.086*
H1B	0.9149	0.1293	0.3311	0.086*
H1C	0.7027	0.1374	0.3557	0.086*
C2	0.7960 (8)	0.4044 (7)	0.1519 (7)	0.0443 (15)
H2A	0.8121	0.3452	0.0977	0.053*
C3	0.7870 (8)	0.5551 (6)	0.0807 (7)	0.0422 (15)
H3A	0.7948	0.5992	−0.0214	0.051*
C4	0.7660 (8)	0.6442 (6)	0.1610 (6)	0.0387 (14)
C5	0.7505 (8)	0.5736 (6)	0.3135 (6)	0.0422 (15)
H5A	0.7337	0.6297	0.3707	0.051*
C6	0.7598 (8)	0.4226 (7)	0.3784 (7)	0.0445 (15)
H6A	0.7506	0.3759	0.4806	0.053*
C7	0.7700 (8)	0.8070 (6)	0.0779 (6)	0.0339 (13)
C8	0.8426 (8)	1.0150 (6)	−0.0938 (6)	0.0395 (14)
C9	0.9152 (8)	1.1306 (7)	−0.2232 (7)	0.0443 (15)
H9A	1.0063	1.1104	−0.2983	0.053*
C10	0.8473 (9)	1.2748 (7)	−0.2354 (7)	0.0498 (17)
H10A	0.8941	1.3536	−0.3202	0.060*
C11	0.7082 (9)	1.3076 (7)	−0.1230 (7)	0.0482 (16)
H11A	0.6644	1.4071	−0.1361	0.058*
C12	0.6369 (8)	1.1955 (6)	0.0047 (7)	0.0423 (15)
H12A	0.5454	1.2161	0.0793	0.051*
C13	0.7076 (7)	1.0494 (6)	0.0175 (6)	0.0344 (13)
C14	0.5260 (8)	0.8957 (7)	0.2645 (7)	0.0478 (16)
H14A	0.5225	0.7909	0.3245	0.072*
H14B	0.4090	0.9405	0.2400	0.072*
H14C	0.5541	0.9438	0.3187	0.072*
I1	0.26309 (6)	0.26836 (5)	0.37099 (4)	0.05037 (19)
N1	0.7821 (6)	0.3387 (5)	0.2996 (6)	0.0432 (12)
N2	0.8779 (7)	0.8606 (5)	−0.0548 (5)	0.0426 (12)
N3	0.6668 (6)	0.9141 (5)	0.1277 (5)	0.0367 (11)

	U11	U22	U33	U12	U13	U23
C1	0.062 (5)	0.042 (4)	0.064 (5)	−0.010 (3)	−0.008 (4)	−0.019 (3)
C2	0.047 (4)	0.049 (4)	0.045 (4)	−0.011 (3)	−0.011 (3)	−0.023 (3)
C3	0.043 (4)	0.046 (4)	0.042 (4)	0.001 (3)	−0.011 (3)	−0.022 (3)
C4	0.030 (3)	0.047 (4)	0.042 (4)	−0.001 (3)	−0.008 (3)	−0.021 (3)
C5	0.046 (4)	0.045 (4)	0.042 (4)	−0.010 (3)	−0.007 (3)	−0.022 (3)
C6	0.053 (4)	0.044 (4)	0.037 (3)	−0.004 (3)	−0.008 (3)	−0.018 (3)
C7	0.032 (3)	0.039 (3)	0.033 (3)	−0.005 (3)	−0.008 (3)	−0.016 (3)
C8	0.043 (4)	0.042 (4)	0.039 (3)	−0.006 (3)	−0.016 (3)	−0.016 (3)
C9	0.045 (4)	0.046 (4)	0.043 (4)	−0.011 (3)	−0.010 (3)	−0.016 (3)
C10	0.052 (4)	0.051 (4)	0.046 (4)	−0.020 (3)	−0.021 (3)	−0.005 (3)
C11	0.048 (4)	0.038 (4)	0.065 (5)	−0.001 (3)	−0.024 (4)	−0.021 (3)
C12	0.041 (4)	0.044 (4)	0.048 (4)	0.001 (3)	−0.013 (3)	−0.024 (3)
C13	0.032 (3)	0.041 (4)	0.036 (3)	−0.003 (3)	−0.014 (3)	−0.017 (3)
C14	0.042 (4)	0.047 (4)	0.053 (4)	−0.004 (3)	−0.008 (3)	−0.021 (3)
I1	0.0493 (3)	0.0535 (3)	0.0478 (3)	−0.0021 (2)	−0.0128 (2)	−0.0197 (2)
N1	0.034 (3)	0.039 (3)	0.057 (3)	−0.003 (2)	−0.013 (3)	−0.017 (3)
N2	0.045 (3)	0.046 (3)	0.044 (3)	−0.006 (2)	−0.014 (3)	−0.021 (2)
N3	0.031 (3)	0.045 (3)	0.038 (3)	−0.004 (2)	−0.009 (2)	−0.020 (3)

C1—N1	1.490 (8)	C8—N2	1.389 (7)
C1—H1A	0.9600	C8—C13	1.397 (8)
C1—H1B	0.9600	C8—C9	1.397 (8)
C1—H1C	0.9600	C9—C10	1.368 (8)
C2—N1	1.343 (7)	C9—H9A	0.9300
C2—C3	1.353 (8)	C10—C11	1.412 (9)
C2—H2A	0.9300	C10—H10A	0.9300
C3—C4	1.395 (7)	C11—C12	1.368 (8)
C3—H3A	0.9300	C11—H11A	0.9300
C4—C5	1.386 (7)	C12—C13	1.388 (7)
C4—C7	1.475 (8)	C12—H12A	0.9300
C5—C6	1.350 (7)	C13—N3	1.369 (7)
C5—H5A	0.9300	C14—N3	1.462 (7)
C6—N1	1.336 (7)	C14—H14A	0.9600
C6—H6A	0.9300	C14—H14B	0.9600
C7—N2	1.318 (7)	C14—H14C	0.9600
C7—N3	1.357 (7)
N1—C1—H1A	109.5	C10—C9—H9A	121.3
N1—C1—H1B	109.5	C8—C9—H9A	121.3
H1A—C1—H1B	109.5	C9—C10—C11	122.1 (6)
N1—C1—H1C	109.5	C9—C10—H10A	119.0
H1A—C1—H1C	109.5	C11—C10—H10A	119.0
H1B—C1—H1C	109.5	C12—C11—C10	121.1 (6)
N1—C2—C3	121.1 (5)	C12—C11—H11A	119.5
N1—C2—H2A	119.5	C10—C11—H11A	119.5
C3—C2—H2A	119.5	C11—C12—C13	116.7 (6)
C2—C3—C4	119.7 (6)	C11—C12—H12A	121.6
C2—C3—H3A	120.1	C13—C12—H12A	121.6
C4—C3—H3A	120.1	N3—C13—C12	131.6 (5)
C5—C4—C3	118.0 (5)	N3—C13—C8	105.5 (5)
C5—C4—C7	123.9 (5)	C12—C13—C8	122.9 (6)
C3—C4—C7	118.1 (5)	N3—C14—H14A	109.5
C6—C5—C4	119.6 (5)	N3—C14—H14B	109.5
C6—C5—H5A	120.2	H14A—C14—H14B	109.5
C4—C5—H5A	120.2	N3—C14—H14C	109.5
N1—C6—C5	121.8 (6)	H14A—C14—H14C	109.5
N1—C6—H6A	119.1	H14B—C14—H14C	109.5
C5—C6—H6A	119.1	C6—N1—C2	119.9 (5)
N2—C7—N3	114.0 (5)	C6—N1—C1	121.0 (5)
N2—C7—C4	121.4 (5)	C2—N1—C1	119.1 (5)
N3—C7—C4	124.6 (5)	C7—N2—C8	103.7 (5)
N2—C8—C13	110.2 (5)	C7—N3—C13	106.5 (5)
N2—C8—C9	130.0 (6)	C7—N3—C14	128.7 (5)
C13—C8—C9	119.8 (5)	C13—N3—C14	124.6 (5)
C10—C9—C8	117.4 (6)
N1—C2—C3—C4	1.1 (9)	N2—C8—C13—C12	−176.0 (5)
C2—C3—C4—C5	−1.6 (9)	C9—C8—C13—C12	1.7 (8)
C2—C3—C4—C7	175.7 (5)	C5—C6—N1—C2	0.1 (9)
C3—C4—C5—C6	1.3 (9)	C5—C6—N1—C1	178.2 (6)
C7—C4—C5—C6	−175.7 (5)	C3—C2—N1—C6	−0.3 (9)
C4—C5—C6—N1	−0.6 (9)	C3—C2—N1—C1	−178.5 (6)
C5—C4—C7—N2	141.4 (6)	N3—C7—N2—C8	0.4 (6)
C3—C4—C7—N2	−35.7 (8)	C4—C7—N2—C8	−179.7 (5)
C5—C4—C7—N3	−38.7 (8)	C13—C8—N2—C7	−1.9 (6)
C3—C4—C7—N3	144.2 (5)	C9—C8—N2—C7	−179.3 (6)
N2—C8—C9—C10	176.4 (5)	N2—C7—N3—C13	1.2 (6)
C13—C8—C9—C10	−0.8 (8)	C4—C7—N3—C13	−178.7 (5)
C8—C9—C10—C11	−0.4 (8)	N2—C7—N3—C14	176.0 (5)
C9—C10—C11—C12	0.9 (9)	C4—C7—N3—C14	−3.8 (8)
C10—C11—C12—C13	−0.1 (8)	C12—C13—N3—C7	176.2 (5)
C11—C12—C13—N3	−179.4 (5)	C8—C13—N3—C7	−2.2 (5)
C11—C12—C13—C8	−1.2 (8)	C12—C13—N3—C14	1.1 (9)
N2—C8—C13—N3	2.6 (6)	C8—C13—N3—C14	−177.3 (5)
C9—C8—C13—N3	−179.7 (5)