1,3-Dibenzyl-2-methyl-benzimidazolium chloride.

The cation of the title salt, C(22)H(21)N(2) (+)·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 = 348.86

Triclinic,

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[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 ▶); 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 ▶).

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

C22H21N2+·Cl−	Z = 2
Mr = 348.86	F(000) = 368
Triclinic, P1	Dx = 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

Bruker APEXII diffractometer	4175 independent reflections
Radiation source: fine-focus sealed tube	3336 reflections with I > 2σ(I)
graphite	Rint = 0.028
φ and ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.938, Tmax = 0.938	k = −12→12
24459 measured reflections	l = −15→15

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(Fo2) + (0.0687P)2 + 0.1373P] where P = (Fo2 + 2Fc2)/3
4175 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
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*

	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)

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)