1,3-Dibenzyl-2-methyl­benzimidazolium chloride

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

doi:10.1107/S1600536810002588

organic compounds

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ISSN: 2056-9890

Volume 66| Part 2| February 2010| Page o455

https://doi.org/10.1107/S1600536810002588

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1,3-Dibenzyl-2-methylbenzimidazolium chloride

Hamid Ennajih,^a Rachid Bouhfid,^a Hafid Zouihri,^b El Mokhtar Essassi ^c and Seik Weng Ng ^d ^*

^aInstitute of Nanomaterials and Nanotechnology, Avenue de l'Armée Royale, Madinat El Irfane, 10100 Rabat, Morocco, ^bCNRST Division of UATRS Angle Allal Fassi/FAR, BP 8027 Hay Riad, 10000 Rabat, Morocco, ^cLaboratoire de Chimie Organique Hétérocyclique, Pôle de Compétences Pharmacochimie, Université Mohammed V-Agdal, BP 1014 Avenue Ibn Batout, Rabat, Morocco, and ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 20 January 2010; accepted 20 January 2010; online 27 January 2010)

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 ).

Experimental

Crystal data

C₂₂H₂₁N₂⁺·Cl⁻
M_r = 348.86
Triclinic, $[P \overline 1]$
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 ) 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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.124
S = 1.08
4175 reflections
227 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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 ).

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810002588/bt5179Isup2.hkl

checkCIF report

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.

Structure description top

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

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

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
M_r = 348.86	F(000) = 368
Triclinic, P1	D_x = 1.271 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2539 (2) Å	Cell parameters from 8258 reflections
b = 9.4677 (2) Å	θ = 2.5–29.1°
c = 12.0984 (3) Å	µ = 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 tube	3336 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
T_min = 0.938, T_max = 0.938	k = −12→12
24459 measured reflections	l = −15→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.08	w = 1/[σ²(F_o²) + (0.0687P)² + 0.1373P] where P = (F_o² + 2F_c²)/3
4175 reflections	(Δ/σ)_max = 0.001
227 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₂H₂₁N₂⁺·Cl⁻	γ = 64.605 (1)°
M_r = 348.86	V = 911.20 (4) Å³
Triclinic, P1	Z = 2
a = 9.2539 (2) Å	Mo Kα radiation
b = 9.4677 (2) Å	µ = 0.22 mm⁻¹
c = 12.0984 (3) Å	T = 293 K
α = 72.139 (1)°	0.30 × 0.30 × 0.30 mm
β = 81.376 (1)°

Data collection top

Bruker APEXII diffractometer	4175 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3336 reflections with I > 2σ(I)
T_min = 0.938, T_max = 0.938	R_int = 0.028
24459 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.08	Δρ_max = 0.23 e Å⁻³
4175 reflections	Δρ_min = −0.23 e Å⁻³
227 parameters

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

	x	y	z	U_iso*/U_eq
Cl1	0.29429 (4)	0.33126 (4)	0.00802 (3)	0.04507 (14)
N1	0.77776 (14)	0.02156 (14)	0.14627 (10)	0.0356 (3)
N2	0.91155 (14)	0.15323 (14)	0.16783 (10)	0.0352 (3)
C1	0.61460 (19)	0.30695 (19)	0.16123 (16)	0.0498 (4)
H1A	0.5794	0.3046	0.2403	0.075*
H1B	0.5340	0.3064	0.1200	0.075*
H1C	0.6328	0.4036	0.1249	0.075*
C2	0.76494 (17)	0.16248 (17)	0.15880 (12)	0.0360 (3)
C3	0.93932 (17)	−0.08252 (17)	0.14577 (12)	0.0349 (3)
C4	1.0170 (2)	−0.23710 (18)	0.12901 (14)	0.0434 (4)
H4	0.9608	−0.2928	0.1179	0.052*
C5	1.1821 (2)	−0.3032 (2)	0.12974 (15)	0.0515 (4)
H5	1.2387	−0.4067	0.1194	0.062*
C6	1.2669 (2)	−0.2194 (2)	0.14549 (16)	0.0541 (4)
H6	1.3781	−0.2688	0.1458	0.065*
C7	1.18996 (19)	−0.0654 (2)	0.16059 (14)	0.0454 (4)
H7	1.2462	−0.0092	0.1704	0.054*
C8	1.02401 (17)	0.00110 (17)	0.16028 (12)	0.0350 (3)
C9	0.64487 (18)	−0.02047 (18)	0.13464 (14)	0.0416 (3)
H9	0.6788	−0.0902	0.0830	0.050*
H9B	0.5545	0.0780	0.1000	0.050*
C10	0.59317 (18)	−0.10561 (18)	0.25015 (14)	0.0411 (3)
C11	0.4779 (2)	−0.0170 (2)	0.3180 (2)	0.0646 (5)
H11	0.4329	0.0959	0.2926	0.078*
C12	0.4288 (3)	−0.0946 (3)	0.4233 (2)	0.0821 (7)
H12	0.3506	−0.0341	0.4682	0.099*
C13	0.4951 (3)	−0.2606 (3)	0.4616 (2)	0.0750 (6)
H13	0.4628	−0.3126	0.5329	0.090*
C14	0.6089 (3)	−0.3505 (3)	0.3951 (2)	0.0668 (5)
H14	0.6539	−0.4633	0.4212	0.080*
C15	0.6566 (2)	−0.2729 (2)	0.28935 (17)	0.0526 (4)
H15	0.7325	−0.3343	0.2438	0.063*
C16	0.95196 (19)	0.28401 (18)	0.17480 (13)	0.0405 (3)
H16	0.8649	0.3876	0.1434	0.049*
H16B	1.0466	0.2809	0.1268	0.049*
C17	0.98260 (18)	0.27339 (17)	0.29640 (13)	0.0380 (3)
C18	0.9089 (2)	0.2087 (2)	0.39402 (15)	0.0533 (4)
H18	0.8402	0.1638	0.3866	0.064*
C19	0.9367 (3)	0.2104 (3)	0.50305 (17)	0.0700 (6)
H19	0.8861	0.1670	0.5682	0.084*
C20	1.0372 (3)	0.2749 (3)	0.5152 (2)	0.0813 (7)
H20	1.0558	0.2754	0.5885	0.098*
C21	1.1109 (3)	0.3392 (3)	0.4191 (2)	0.0821 (7)
H21	1.1794	0.3838	0.4274	0.099*
C22	1.0846 (2)	0.3384 (2)	0.31030 (18)	0.0574 (5)
H22	1.1359	0.3820	0.2457	0.069*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0415 (2)	0.0398 (2)	0.0544 (2)	−0.01604 (16)	−0.00553 (16)	−0.01205 (16)
N1	0.0346 (6)	0.0361 (6)	0.0407 (6)	−0.0176 (5)	−0.0027 (5)	−0.0109 (5)
N2	0.0371 (6)	0.0385 (6)	0.0354 (6)	−0.0199 (5)	−0.0011 (5)	−0.0107 (5)
C1	0.0415 (9)	0.0420 (8)	0.0686 (11)	−0.0158 (7)	−0.0026 (8)	−0.0196 (8)
C2	0.0385 (7)	0.0371 (7)	0.0366 (7)	−0.0191 (6)	−0.0017 (6)	−0.0098 (6)
C3	0.0364 (7)	0.0378 (7)	0.0309 (7)	−0.0168 (6)	−0.0005 (5)	−0.0076 (5)
C4	0.0486 (9)	0.0399 (8)	0.0437 (8)	−0.0196 (7)	0.0023 (7)	−0.0133 (6)
C5	0.0488 (9)	0.0421 (8)	0.0559 (10)	−0.0122 (7)	0.0056 (8)	−0.0155 (7)
C6	0.0362 (8)	0.0562 (10)	0.0601 (10)	−0.0120 (7)	0.0031 (7)	−0.0147 (8)
C7	0.0374 (8)	0.0555 (9)	0.0460 (9)	−0.0224 (7)	−0.0002 (6)	−0.0125 (7)
C8	0.0372 (7)	0.0397 (7)	0.0303 (7)	−0.0181 (6)	−0.0002 (5)	−0.0093 (5)
C9	0.0385 (8)	0.0411 (7)	0.0527 (9)	−0.0201 (6)	−0.0082 (7)	−0.0139 (7)
C10	0.0343 (7)	0.0437 (8)	0.0543 (9)	−0.0211 (6)	−0.0024 (6)	−0.0171 (7)
C11	0.0597 (11)	0.0542 (10)	0.0887 (15)	−0.0312 (9)	0.0230 (10)	−0.0311 (10)
C12	0.0870 (16)	0.0893 (16)	0.0946 (17)	−0.0553 (14)	0.0443 (14)	−0.0511 (14)
C13	0.0851 (16)	0.0911 (16)	0.0633 (13)	−0.0583 (14)	0.0143 (11)	−0.0146 (11)
C14	0.0671 (12)	0.0537 (10)	0.0756 (13)	−0.0304 (10)	−0.0002 (10)	−0.0043 (10)
C15	0.0498 (10)	0.0451 (9)	0.0647 (11)	−0.0213 (8)	0.0049 (8)	−0.0171 (8)
C16	0.0460 (8)	0.0400 (7)	0.0427 (8)	−0.0255 (7)	−0.0023 (6)	−0.0084 (6)
C17	0.0377 (7)	0.0307 (6)	0.0463 (8)	−0.0109 (6)	−0.0046 (6)	−0.0141 (6)
C18	0.0619 (11)	0.0563 (10)	0.0450 (9)	−0.0277 (9)	−0.0002 (8)	−0.0134 (8)
C19	0.0869 (15)	0.0691 (13)	0.0454 (10)	−0.0223 (11)	−0.0005 (10)	−0.0183 (9)
C20	0.1008 (18)	0.0796 (15)	0.0648 (14)	−0.0186 (13)	−0.0261 (13)	−0.0366 (12)
C21	0.0938 (17)	0.0875 (16)	0.0920 (17)	−0.0434 (14)	−0.0242 (14)	−0.0406 (14)
C22	0.0606 (11)	0.0575 (10)	0.0691 (12)	−0.0315 (9)	−0.0070 (9)	−0.0236 (9)

Geometric parameters (Å, º) top

N1—C2	1.3416 (18)	C10—C11	1.382 (2)
N1—C3	1.3941 (18)	C11—C12	1.381 (3)
N1—C9	1.4821 (18)	C11—H11	0.9300
N2—C2	1.3406 (18)	C12—C13	1.368 (3)
N2—C8	1.3902 (18)	C12—H12	0.9300
N2—C16	1.4664 (18)	C13—C14	1.370 (3)
C1—C2	1.479 (2)	C13—H13	0.9300
C1—H1A	0.9600	C14—C15	1.380 (3)
C1—H1B	0.9600	C14—H14	0.9300
C1—H1C	0.9600	C15—H15	0.9300
C3—C8	1.389 (2)	C16—C17	1.505 (2)
C3—C4	1.391 (2)	C16—H16	0.9700
C4—C5	1.381 (2)	C16—H16B	0.9700
C4—H4	0.9300	C17—C22	1.381 (2)
C5—C6	1.397 (3)	C17—C18	1.381 (2)
C5—H5	0.9300	C18—C19	1.387 (3)
C6—C7	1.378 (2)	C18—H18	0.9300
C6—H6	0.9300	C19—C20	1.358 (4)
C7—C8	1.388 (2)	C19—H19	0.9300
C7—H7	0.9300	C20—C21	1.368 (4)
C9—C10	1.507 (2)	C20—H20	0.9300
C9—H9	0.9700	C21—C22	1.377 (3)
C9—H9B	0.9700	C21—H21	0.9300
C10—C15	1.380 (2)	C22—H22	0.9300

C2—N1—C3	108.77 (12)	C11—C10—C9	120.38 (15)
C2—N1—C9	126.81 (12)	C10—C11—C12	120.55 (19)
C3—N1—C9	124.43 (12)	C10—C11—H11	119.7
C2—N2—C8	108.89 (12)	C12—C11—H11	119.7
C2—N2—C16	126.78 (13)	C13—C12—C11	120.0 (2)
C8—N2—C16	124.15 (12)	C13—C12—H12	120.0
C2—C1—H1A	109.5	C11—C12—H12	120.0
C2—C1—H1B	109.5	C14—C13—C12	120.2 (2)
H1A—C1—H1B	109.5	C14—C13—H13	119.9
C2—C1—H1C	109.5	C12—C13—H13	119.9
H1A—C1—H1C	109.5	C13—C14—C15	119.71 (19)
H1B—C1—H1C	109.5	C13—C14—H14	120.1
N2—C2—N1	109.12 (13)	C15—C14—H14	120.1
N2—C2—C1	124.66 (13)	C10—C15—C14	120.95 (18)
N1—C2—C1	126.21 (13)	C10—C15—H15	119.5
C8—C3—C4	121.57 (14)	C14—C15—H15	119.5
C8—C3—N1	106.52 (12)	N2—C16—C17	113.56 (12)
C4—C3—N1	131.83 (14)	N2—C16—H16	108.9
C5—C4—C3	116.23 (15)	C17—C16—H16	108.9
C5—C4—H4	121.9	N2—C16—H16B	108.9
C3—C4—H4	121.9	C17—C16—H16B	108.9
C4—C5—C6	122.05 (16)	H16—C16—H16B	107.7
C4—C5—H5	119.0	C22—C17—C18	118.45 (16)
C6—C5—H5	119.0	C22—C17—C16	117.98 (14)
C7—C6—C5	121.71 (16)	C18—C17—C16	123.51 (14)
C7—C6—H6	119.1	C17—C18—C19	120.39 (18)
C5—C6—H6	119.1	C17—C18—H18	119.8
C6—C7—C8	116.38 (15)	C19—C18—H18	119.8
C6—C7—H7	121.8	C20—C19—C18	120.4 (2)
C8—C7—H7	121.8	C20—C19—H19	119.8
C7—C8—C3	122.05 (14)	C18—C19—H19	119.8
C7—C8—N2	131.20 (14)	C19—C20—C21	119.68 (19)
C3—C8—N2	106.69 (12)	C19—C20—H20	120.2
N1—C9—C10	111.98 (12)	C21—C20—H20	120.2
N1—C9—H9	109.2	C20—C21—C22	120.6 (2)
C10—C9—H9	109.2	C20—C21—H21	119.7
N1—C9—H9B	109.2	C22—C21—H21	119.7
C10—C9—H9B	109.2	C21—C22—C17	120.4 (2)
H9—C9—H9B	107.9	C21—C22—H22	119.8
C15—C10—C11	118.51 (16)	C17—C22—H22	119.8
C15—C10—C9	121.09 (15)

C8—N2—C2—N1	0.33 (16)	C16—N2—C8—C3	−175.22 (12)
C16—N2—C2—N1	175.59 (12)	C2—N1—C9—C10	−93.34 (17)
C8—N2—C2—C1	−179.08 (14)	C3—N1—C9—C10	86.67 (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—C11	88.23 (18)
C9—N1—C2—N2	179.28 (13)	C15—C10—C11—C12	0.7 (3)
C3—N1—C2—C1	178.67 (14)	C9—C10—C11—C12	179.22 (19)
C9—N1—C2—C1	−1.3 (2)	C10—C11—C12—C13	0.4 (4)
C2—N1—C3—C8	0.84 (15)	C11—C12—C13—C14	−0.8 (4)
C9—N1—C3—C8	−179.17 (12)	C12—C13—C14—C15	0.0 (4)
C2—N1—C3—C4	−175.93 (15)	C11—C10—C15—C14	−1.5 (3)
C9—N1—C3—C4	4.1 (2)	C9—C10—C15—C14	−179.97 (16)
C8—C3—C4—C5	1.1 (2)	C13—C14—C15—C10	1.1 (3)
N1—C3—C4—C5	177.47 (15)	C2—N2—C16—C17	100.24 (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—C22	152.21 (15)
C5—C6—C7—C8	0.5 (3)	N2—C16—C17—C18	−30.7 (2)
C6—C7—C8—C3	0.1 (2)	C22—C17—C18—C19	0.4 (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—C21	0.3 (4)
C4—C3—C8—N2	176.55 (13)	C19—C20—C21—C22	−0.3 (4)
N1—C3—C8—N2	−0.62 (14)	C20—C21—C22—C17	0.3 (3)
C2—N2—C8—C7	177.39 (15)	C18—C17—C22—C21	−0.4 (3)
C16—N2—C8—C7	2.0 (2)	C16—C17—C22—C21	176.83 (18)
C2—N2—C8—C3	0.20 (15)

Experimental details

Crystal data
Chemical formula	C₂₂H₂₁N₂⁺·Cl⁻
M_r	348.86
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.2539 (2), 9.4677 (2), 12.0984 (3)
α, β, γ (°)	72.139 (1), 81.376 (1), 64.605 (1)
V (Å³)	911.20 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.22
Crystal size (mm)	0.30 × 0.30 × 0.30

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.938, 0.938
No. of measured, independent and observed [I > 2σ(I)] reflections	24459, 4175, 3336
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.124, 1.08
No. of reflections	4175
No. of parameters	227
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Acknowledgements

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

References

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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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