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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o455.
Published online 2010 January 27. doi:  10.1107/S1600536810002588
PMCID: PMC2979785

1,3-Dibenzyl-2-methyl­benzimidazolium chloride

Abstract

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

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

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Object name is e-66-0o455-scheme1.jpg

Experimental

Crystal data

  • C22H21N2 +·Cl
  • M r = 348.86
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o455-efi1.jpg
  • a = 9.2539 (2) Å
  • b = 9.4677 (2) Å
  • c = 12.0984 (3) Å
  • α = 72.139 (1)°
  • β = 81.376 (1)°
  • γ = 64.605 (1)°
  • V = 911.20 (4) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.22 mm−1
  • T = 293 K
  • 0.30 × 0.30 × 0.30 mm

Data collection

  • Bruker APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.938, T max = 0.938
  • 24459 measured reflections
  • 4175 independent reflections
  • 3336 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.038
  • wR(F 2) = 0.124
  • S = 1.08
  • 4175 reflections
  • 227 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.23 e Å−3

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

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810002588/bt5179sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810002588/bt5179Isup2.hkl

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

Acknowledgments

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

supplementary crystallographic information

Experimental

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

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).

Figures

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.

Crystal data

C22H21N2+·ClZ = 2
Mr = 348.86F(000) = 368
Triclinic, P1Dx = 1.271 Mg m3
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 mm1
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

Bruker APEXII diffractometer4175 independent reflections
Radiation source: fine-focus sealed tube3336 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] 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

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 = 1.08w = 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 Å3
0 restraintsΔρmin = −0.23 e Å3

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

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)

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, °)

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)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5179).

References

  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2005). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Jian, F.-F., Wang, H.-X., Xiao, H.-L. & Liu, G.-Y. (2003). Chin. J. Struct. Chem.22, 669–672.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

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