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Acta Cryst. (2010). E66, o455    [ doi:10.1107/S1600536810002588 ]

1,3-Dibenzyl-2-methylbenzimidazolium chloride

H. Ennajih, R. Bouhfid, H. Zouihri, E. M. Essassi and S. W. Ng

Abstract top

The cation of the title salt, C22H21N2+·Cl-, contains a planar benzimidazolium unit (r.m.s. deviation = 0.02 Å); the phenyl rings of the benzyl substituents form dihedral angles of 68.2 (1) and 79.7 (1)° with the plane of the benzimidazolium fragment.

Related literature top

For the crystal structure of the monohydrated salt, see: Jian et al. (2003).

Experimental top

To a solution of 2-methylbenzimidazole (1 g, 7.57 mmol) in DMF (20 ml) was added benzyl chloride (2,66 ml, 22.7 mmol), potassium carbonate (1.25 g, 9.08 mmol) and a catalytic amount of tetra-n-butylammonium bromide. The mixture was stirred for 24 h. The solution was filtered and the solvent removed under reduced pressure. The residue was recrystallized from ethanol to afford 1,3-dibenzyl-2-methyl-benzimidazolium chloride as colorless crystals.

Refinement top

H-atoms were placed in calculated positions (C—H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2–1.5U(C).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of the title compound at the 50% probability level; hydrogen atoms are drawn as spheres of an arbitrary radius.
1,3-Dibenzyl-2-methylbenzimidazolium chloride top
Crystal data top
C22H21N2+·Cl−Z = 2
Mr = 348.86F(000) = 368
Triclinic, P1Dx = 1.271 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2539 (2) ÅCell parameters from 8258 reflections
b = 9.4677 (2) Åθ = 2.5–29.1°
c = 12.0984 (3) ŵ = 0.22 mm−1
α = 72.139 (1)°T = 293 K
β = 81.376 (1)°Block, colorless
γ = 64.605 (1)°0.30 × 0.30 × 0.30 mm
V = 911.20 (4) Å3
Data collection top
Bruker APEXII
diffractometer		4175 independent reflections
Radiation source: fine-focus sealed tube3336 reflections with I > 2σ(I)
graphiteRint = 0.028
φ and ω scansθmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		h = −12→12
Tmin = 0.938, Tmax = 0.938k = −12→12
24459 measured reflectionsl = −15→15
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.124H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0687P)2 + 0.1373P]
where P = (Fo2 + 2Fc2)/3
4175 reflections(Δ/σ)max = 0.001
227 parametersΔρmax = 0.23 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Crystal data top
C22H21N2+·Cl−γ = 64.605 (1)°
Mr = 348.86V = 911.20 (4) Å3
Triclinic, P1Z = 2
a = 9.2539 (2) ÅMo Kα radiation
b = 9.4677 (2) ŵ = 0.22 mm−1
c = 12.0984 (3) ÅT = 293 K
α = 72.139 (1)°0.30 × 0.30 × 0.30 mm
β = 81.376 (1)°
Data collection top
Bruker APEXII
diffractometer		3336 reflections with I > 2σ(I)
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)		Rint = 0.028
Tmin = 0.938, Tmax = 0.938θmax = 27.5°
24459 measured reflectionsStandard reflections: 0
4175 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.038H-atom parameters constrained
wR(F2) = 0.124Δρmax = 0.23 e Å−3
S = 1.08Δρmin = −0.23 e Å−3
4175 reflectionsAbsolute structure: ?
227 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Cl10.29429 (4)0.33126 (4)0.00802 (3)0.04507 (14)
N10.77776 (14)0.02156 (14)0.14627 (10)0.0356 (3)
N20.91155 (14)0.15323 (14)0.16783 (10)0.0352 (3)
C10.61460 (19)0.30695 (19)0.16123 (16)0.0498 (4)
H1A0.57940.30460.24030.075*
H1B0.53400.30640.12000.075*
H1C0.63280.40360.12490.075*
C20.76494 (17)0.16248 (17)0.15880 (12)0.0360 (3)
C30.93932 (17)−0.08252 (17)0.14577 (12)0.0349 (3)
C41.0170 (2)−0.23710 (18)0.12901 (14)0.0434 (4)
H40.9608−0.29280.11790.052*
C51.1821 (2)−0.3032 (2)0.12974 (15)0.0515 (4)
H51.2387−0.40670.11940.062*
C61.2669 (2)−0.2194 (2)0.14549 (16)0.0541 (4)
H61.3781−0.26880.14580.065*
C71.18996 (19)−0.0654 (2)0.16059 (14)0.0454 (4)
H71.2462−0.00920.17040.054*
C81.02401 (17)0.00110 (17)0.16028 (12)0.0350 (3)
C90.64487 (18)−0.02047 (18)0.13464 (14)0.0416 (3)
H90.6788−0.09020.08300.050*
H9B0.55450.07800.10000.050*
C100.59317 (18)−0.10561 (18)0.25015 (14)0.0411 (3)
C110.4779 (2)−0.0170 (2)0.3180 (2)0.0646 (5)
H110.43290.09590.29260.078*
C120.4288 (3)−0.0946 (3)0.4233 (2)0.0821 (7)
H120.3506−0.03410.46820.099*
C130.4951 (3)−0.2606 (3)0.4616 (2)0.0750 (6)
H130.4628−0.31260.53290.090*
C140.6089 (3)−0.3505 (3)0.3951 (2)0.0668 (5)
H140.6539−0.46330.42120.080*
C150.6566 (2)−0.2729 (2)0.28935 (17)0.0526 (4)
H150.7325−0.33430.24380.063*
C160.95196 (19)0.28401 (18)0.17480 (13)0.0405 (3)
H160.86490.38760.14340.049*
H16B1.04660.28090.12680.049*
C170.98260 (18)0.27339 (17)0.29640 (13)0.0380 (3)
C180.9089 (2)0.2087 (2)0.39402 (15)0.0533 (4)
H180.84020.16380.38660.064*
C190.9367 (3)0.2104 (3)0.50305 (17)0.0700 (6)
H190.88610.16700.56820.084*
C201.0372 (3)0.2749 (3)0.5152 (2)0.0813 (7)
H201.05580.27540.58850.098*
C211.1109 (3)0.3392 (3)0.4191 (2)0.0821 (7)
H211.17940.38380.42740.099*
C221.0846 (2)0.3384 (2)0.31030 (18)0.0574 (5)
H221.13590.38200.24570.069*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0415 (2)0.0398 (2)0.0544 (2)−0.01604 (16)−0.00553 (16)−0.01205 (16)
N10.0346 (6)0.0361 (6)0.0407 (6)−0.0176 (5)−0.0027 (5)−0.0109 (5)
N20.0371 (6)0.0385 (6)0.0354 (6)−0.0199 (5)−0.0011 (5)−0.0107 (5)
C10.0415 (9)0.0420 (8)0.0686 (11)−0.0158 (7)−0.0026 (8)−0.0196 (8)
C20.0385 (7)0.0371 (7)0.0366 (7)−0.0191 (6)−0.0017 (6)−0.0098 (6)
C30.0364 (7)0.0378 (7)0.0309 (7)−0.0168 (6)−0.0005 (5)−0.0076 (5)
C40.0486 (9)0.0399 (8)0.0437 (8)−0.0196 (7)0.0023 (7)−0.0133 (6)
C50.0488 (9)0.0421 (8)0.0559 (10)−0.0122 (7)0.0056 (8)−0.0155 (7)
C60.0362 (8)0.0562 (10)0.0601 (10)−0.0120 (7)0.0031 (7)−0.0147 (8)
C70.0374 (8)0.0555 (9)0.0460 (9)−0.0224 (7)−0.0002 (6)−0.0125 (7)
C80.0372 (7)0.0397 (7)0.0303 (7)−0.0181 (6)−0.0002 (5)−0.0093 (5)
C90.0385 (8)0.0411 (7)0.0527 (9)−0.0201 (6)−0.0082 (7)−0.0139 (7)
C100.0343 (7)0.0437 (8)0.0543 (9)−0.0211 (6)−0.0024 (6)−0.0171 (7)
C110.0597 (11)0.0542 (10)0.0887 (15)−0.0312 (9)0.0230 (10)−0.0311 (10)
C120.0870 (16)0.0893 (16)0.0946 (17)−0.0553 (14)0.0443 (14)−0.0511 (14)
C130.0851 (16)0.0911 (16)0.0633 (13)−0.0583 (14)0.0143 (11)−0.0146 (11)
C140.0671 (12)0.0537 (10)0.0756 (13)−0.0304 (10)−0.0002 (10)−0.0043 (10)
C150.0498 (10)0.0451 (9)0.0647 (11)−0.0213 (8)0.0049 (8)−0.0171 (8)
C160.0460 (8)0.0400 (7)0.0427 (8)−0.0255 (7)−0.0023 (6)−0.0084 (6)
C170.0377 (7)0.0307 (6)0.0463 (8)−0.0109 (6)−0.0046 (6)−0.0141 (6)
C180.0619 (11)0.0563 (10)0.0450 (9)−0.0277 (9)−0.0002 (8)−0.0134 (8)
C190.0869 (15)0.0691 (13)0.0454 (10)−0.0223 (11)−0.0005 (10)−0.0183 (9)
C200.1008 (18)0.0796 (15)0.0648 (14)−0.0186 (13)−0.0261 (13)−0.0366 (12)
C210.0938 (17)0.0875 (16)0.0920 (17)−0.0434 (14)−0.0242 (14)−0.0406 (14)
C220.0606 (11)0.0575 (10)0.0691 (12)−0.0315 (9)−0.0070 (9)−0.0236 (9)
Geometric parameters (Å, °) top
N1—C21.3416 (18)C10—C111.382 (2)
N1—C31.3941 (18)C11—C121.381 (3)
N1—C91.4821 (18)C11—H110.9300
N2—C21.3406 (18)C12—C131.368 (3)
N2—C81.3902 (18)C12—H120.9300
N2—C161.4664 (18)C13—C141.370 (3)
C1—C21.479 (2)C13—H130.9300
C1—H1A0.9600C14—C151.380 (3)
C1—H1B0.9600C14—H140.9300
C1—H1C0.9600C15—H150.9300
C3—C81.389 (2)C16—C171.505 (2)
C3—C41.391 (2)C16—H160.9700
C4—C51.381 (2)C16—H16B0.9700
C4—H40.9300C17—C221.381 (2)
C5—C61.397 (3)C17—C181.381 (2)
C5—H50.9300C18—C191.387 (3)
C6—C71.378 (2)C18—H180.9300
C6—H60.9300C19—C201.358 (4)
C7—C81.388 (2)C19—H190.9300
C7—H70.9300C20—C211.368 (4)
C9—C101.507 (2)C20—H200.9300
C9—H90.9700C21—C221.377 (3)
C9—H9B0.9700C21—H210.9300
C10—C151.380 (2)C22—H220.9300
C2—N1—C3108.77 (12)C11—C10—C9120.38 (15)
C2—N1—C9126.81 (12)C10—C11—C12120.55 (19)
C3—N1—C9124.43 (12)C10—C11—H11119.7
C2—N2—C8108.89 (12)C12—C11—H11119.7
C2—N2—C16126.78 (13)C13—C12—C11120.0 (2)
C8—N2—C16124.15 (12)C13—C12—H12120.0
C2—C1—H1A109.5C11—C12—H12120.0
C2—C1—H1B109.5C14—C13—C12120.2 (2)
H1A—C1—H1B109.5C14—C13—H13119.9
C2—C1—H1C109.5C12—C13—H13119.9
H1A—C1—H1C109.5C13—C14—C15119.71 (19)
H1B—C1—H1C109.5C13—C14—H14120.1
N2—C2—N1109.12 (13)C15—C14—H14120.1
N2—C2—C1124.66 (13)C10—C15—C14120.95 (18)
N1—C2—C1126.21 (13)C10—C15—H15119.5
C8—C3—C4121.57 (14)C14—C15—H15119.5
C8—C3—N1106.52 (12)N2—C16—C17113.56 (12)
C4—C3—N1131.83 (14)N2—C16—H16108.9
C5—C4—C3116.23 (15)C17—C16—H16108.9
C5—C4—H4121.9N2—C16—H16B108.9
C3—C4—H4121.9C17—C16—H16B108.9
C4—C5—C6122.05 (16)H16—C16—H16B107.7
C4—C5—H5119.0C22—C17—C18118.45 (16)
C6—C5—H5119.0C22—C17—C16117.98 (14)
C7—C6—C5121.71 (16)C18—C17—C16123.51 (14)
C7—C6—H6119.1C17—C18—C19120.39 (18)
C5—C6—H6119.1C17—C18—H18119.8
C6—C7—C8116.38 (15)C19—C18—H18119.8
C6—C7—H7121.8C20—C19—C18120.4 (2)
C8—C7—H7121.8C20—C19—H19119.8
C7—C8—C3122.05 (14)C18—C19—H19119.8
C7—C8—N2131.20 (14)C19—C20—C21119.68 (19)
C3—C8—N2106.69 (12)C19—C20—H20120.2
N1—C9—C10111.98 (12)C21—C20—H20120.2
N1—C9—H9109.2C20—C21—C22120.6 (2)
C10—C9—H9109.2C20—C21—H21119.7
N1—C9—H9B109.2C22—C21—H21119.7
C10—C9—H9B109.2C21—C22—C17120.4 (2)
H9—C9—H9B107.9C21—C22—H22119.8
C15—C10—C11118.51 (16)C17—C22—H22119.8
C15—C10—C9121.09 (15)
C8—N2—C2—N10.33 (16)C16—N2—C8—C3−175.22 (12)
C16—N2—C2—N1175.59 (12)C2—N1—C9—C10−93.34 (17)
C8—N2—C2—C1−179.08 (14)C3—N1—C9—C1086.67 (17)
C16—N2—C2—C1−3.8 (2)N1—C9—C10—C15−93.28 (17)
C3—N1—C2—N2−0.73 (16)N1—C9—C10—C1188.23 (18)
C9—N1—C2—N2179.28 (13)C15—C10—C11—C120.7 (3)
C3—N1—C2—C1178.67 (14)C9—C10—C11—C12179.22 (19)
C9—N1—C2—C1−1.3 (2)C10—C11—C12—C130.4 (4)
C2—N1—C3—C80.84 (15)C11—C12—C13—C14−0.8 (4)
C9—N1—C3—C8−179.17 (12)C12—C13—C14—C150.0 (4)
C2—N1—C3—C4−175.93 (15)C11—C10—C15—C14−1.5 (3)
C9—N1—C3—C44.1 (2)C9—C10—C15—C14−179.97 (16)
C8—C3—C4—C51.1 (2)C13—C14—C15—C101.1 (3)
N1—C3—C4—C5177.47 (15)C2—N2—C16—C17100.24 (17)
C3—C4—C5—C6−0.5 (2)C8—N2—C16—C17−85.18 (17)
C4—C5—C6—C7−0.3 (3)N2—C16—C17—C22152.21 (15)
C5—C6—C7—C80.5 (3)N2—C16—C17—C18−30.7 (2)
C6—C7—C8—C30.1 (2)C22—C17—C18—C190.4 (3)
C6—C7—C8—N2−176.73 (15)C16—C17—C18—C19−176.69 (16)
C4—C3—C8—C7−1.0 (2)C17—C18—C19—C20−0.3 (3)
N1—C3—C8—C7−178.13 (13)C18—C19—C20—C210.3 (4)
C4—C3—C8—N2176.55 (13)C19—C20—C21—C22−0.3 (4)
N1—C3—C8—N2−0.62 (14)C20—C21—C22—C170.3 (3)
C2—N2—C8—C7177.39 (15)C18—C17—C22—C21−0.4 (3)
C16—N2—C8—C72.0 (2)C16—C17—C22—C21176.83 (18)
C2—N2—C8—C30.20 (15)
Acknowledgements top

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

references
References top

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Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.

Westrip, S. P. (2010). publCIF. In preparation.