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

Wang, F.-M.

doi:10.1107/S1600536809053938

organic compounds

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ISSN: 2056-9890

Volume 66| Part 1| January 2010| Page o198

doi:10.1107/S1600536809053938

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

Fang-Ming Wang ^a ^*

^aSchool of Materials Science and Engineering, Jiangsu University of Science and Technology, Zhenjiang 212003, People's Republic of China
^*Correspondence e-mail: wangfmzj@yahoo.com.cn

(Received 22 November 2009; accepted 15 December 2009; online 19 December 2009)

The cation of the title compound, C₁₄H₁₄N₃⁺·I⁻, is non-planar, the dihedral angle between the benzimidazole and the 1-methylpyridinium planes being 37.4 (2)°. The crystal structure is stabilized by weak π–π stacking interactions, the centroid–centroid distances between 1-methylimidazole 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_r = 351.18
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.043
wR(F²) = 0.092
S = 1.00
2307 reflections
163 parameters
H-atom parameters constrained
Δρ_max = 0.94 e Å⁻³
Δρ_min = −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.

Supporting information

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

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

checkCIF report

Comment top

Imidazole and its derivatives are a very important kind of heterocyclic compounds with N-donor atoms, therefore they can be excellent organic ligands to generate various complexes (Huang et al., 2004). Owing to its biological activities such as antimicrobial, antifungal (Pawar et al., 2004), anticancer (Demirayak et al., 2002), and so on, benzimidazoles have also received much attention. The construction of new member of this family is an important direction in the development of modern coordination chemistry and biological chemistry. We report here the synthesis and crystal structure of the title compound. The molecular structure is shown in Fig. 1. The cation of (I) is non-planar, the dihedral angle between the benzimidazolyl plane and the N-methylpyridinium plane is 37.4 (2)°. The crystal structure is stabilized by π–π [Cg1: N2-C7-N3-C13-C8; Cg2(i): C8/C13, code symmetry: (i) -x+2, -y+1, -z] stacking interaction, the distance centroid-centroid between these planes is 3.678 (4) Å. The crystal packing also exhibits a weak intermolecular C—H···I interaction.

Related literature top

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 top

Metallic sodium (0.25 g, 10.8 mmol) was dissolved in the stirred anhydrous ethanol(10 ml) under an atmosphere of nitrogen. Then added 2-(4-pyridinyl)-1H-benzimidazole (1.95 g, 10 mmol), dry actone (150 ml) and methyl iodide(1.24 ml, 20 mmol) in the above solution. The reaction mixture was refluxed for 24 h. When the reaction stopped and the mixture were cooled to room temperature, the solution were removed under decompression. Then the residue recrystallized from water twice to obtain the single crystals (3.0 g, 8.66 mmol).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The asymmetric unit of the title compound with atom labels. Displacement ellipsoids were drawn at the 30% probability level.

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

Crystal data top

C₁₄H₁₄N₃⁺·I⁻	Z = 2
M_r = 351.18	F(000) = 344
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0301P)²] where P = (F_o² + 2F_c²)/3
2307 reflections	(Δ/σ)_max < 0.001
163 parameters	Δρ_max = 0.94 e Å⁻³
0 restraints	Δρ_min = −0.48 e Å⁻³

Crystal data top

C₁₄H₁₄N₃⁺·I⁻	γ = 76.394 (4)°
M_r = 351.18	V = 668.2 (2) Å³
Triclinic, P1	Z = 2
a = 7.7048 (15) Å	Mo Kα radiation
b = 9.9264 (18) Å	µ = 2.38 mm⁻¹
c = 10.1772 (19) Å	T = 291 K
α = 64.888 (3)°	0.35 × 0.25 × 0.05 mm
β = 72.933 (3)°

Data collection top

Bruker SMART CCD area-detector diffractometer	2307 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000)	1840 reflections with I > 2σ(I)
T_min = 0.493, T_max = 0.887	R_int = 0.058
3353 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.092	H-atom parameters constrained
S = 1.00	Δρ_max = 0.94 e Å⁻³
2307 reflections	Δρ_min = −0.48 e Å⁻³
163 parameters

Special details top

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) C6

Rms deviation of fitted atoms = 0.0044

6.8822 (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) N3

Rms 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₄N₃⁺·I⁻
M_r	351.18
Crystal system, space group	Triclinic, P1
Temperature (K)	291
a, b, c (Å)	7.7048 (15), 9.9264 (18), 10.1772 (19)
α, β, γ (°)	64.888 (3), 72.933 (3), 76.394 (4)
V (Å³)	668.2 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	2.38
Crystal size (mm)	0.35 × 0.25 × 0.05

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000)
T_min, T_max	0.493, 0.887
No. of measured, independent and observed [I > 2σ(I)] reflections	3353, 2307, 1840
R_int	0.058
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.092, 1.00
No. of reflections	2307
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.94, −0.48

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Acknowledgements

This work was supported by a start-up grant from Jiangsu University of Science and Technology.

References

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