2-(Chloro-meth-yl)benzimidazolium chloride.

The structure of title compound, C(8)H(8)ClN(2) (+)·Cl(-), comprises discrete ions which are inter-connected by N-H⋯Cl hydrogen bonds, leading to a neutral one-dimensional network in [001]. This hydrogen bonding appears to complement π-π stacking inter-actions [centroid-centroid distances 3.768 (2) and 3.551 (2) Å] and helps to stabilize the structure further.

Related literature

For details of the preparation of imidazole compounds, see: Ikezaki & Nakamura (2002 ▶). For the chemistry of 2-(chloro­meth­yl)-1H-benzo[d]imidazolium chloride, see: Jian et al. (2003 ▶).

Experimental

Crystal data

C8H8ClN2 +·Cl−

M = 203.06

Monoclinic,

a = 7.1972 (14) Å

b = 9.4507 (19) Å

c = 14.046 (3) Å

β = 102.51 (3)°

V = 932.7 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.64 mm−1

T = 293 K

0.22 × 0.20 × 0.20 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.867, T max = 0.882

9462 measured reflections

2141 independent reflections

1212 reflections with I > 2σ(I)

R int = 0.083

Standard reflections: ?

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.180

S = 0.84

2141 reflections

109 parameters

.

Δρmax = 0.29 e Å−3

Δρmin = −0.31 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL/PC (Sheldrick, 2008 ▶); software used to prepare material for publication: PRPKAPPA (Ferguson, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015359/bx2205sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015359/bx2205Isup2.hkl

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

C8H8ClN2+·Cl−	F(000) = 416
Mr = 203.06	Dx = 1.446 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2ybc	Cell parameters from 1979 reflections
a = 7.1972 (14) Å	θ = 3.1–27.5°
b = 9.4507 (19) Å	µ = 0.64 mm−1
c = 14.046 (3) Å	T = 293 K
β = 102.51 (3)°	Prism, colourless
V = 932.7 (3) Å3	0.22 × 0.20 × 0.20 mm
Z = 4

Rigaku SCXmini diffractometer	2141 independent reflections
Radiation source: fine-focus sealed tube	1212 reflections with I > 2σ(I)
graphite	Rint = 0.083
CCD_Profile_fitting scans	θmax = 27.5°, θmin = 3.6°
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	h = −9→9
Tmin = 0.867, Tmax = 0.882	k = −12→12
9462 measured reflections	l = −18→18

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	w = 1/[σ2(Fo2) + (0.1077P)2 + 0.4199P] where P = (Fo2 + 2Fc2)/3
S = 0.84	(Δ/σ)max < 0.001
2141 reflections	Δρmax = 0.29 e Å−3
109 parameters	Δρmin = −0.31 e Å−3
0 restraints

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

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.

	x	y	z	Uiso*/Ueq
Cl1	0.34571 (17)	0.59201 (10)	1.15934 (7)	0.0608 (4)
Cl2	0.11234 (16)	0.56643 (10)	0.83757 (8)	0.0654 (4)
N2	0.2890 (4)	0.8248 (3)	1.00495 (19)	0.0449 (7)
H2A	0.3032	0.7611	1.0496	0.054*
N1	0.2626 (4)	0.9234 (3)	0.86427 (19)	0.0446 (7)
H1A	0.2575	0.9338	0.8029	0.053*
C6	0.2574 (4)	0.9674 (4)	1.0180 (2)	0.0385 (8)
C1	0.2393 (5)	1.0306 (3)	0.9280 (2)	0.0388 (8)
C7	0.2936 (5)	0.8027 (4)	0.9125 (3)	0.0438 (8)
C5	0.2467 (5)	1.0453 (4)	1.1012 (3)	0.0528 (10)
H5A	0.2596	1.0028	1.1620	0.063*
C2	0.2079 (5)	1.1754 (4)	0.9153 (3)	0.0528 (10)
H2B	0.1957	1.2183	0.8546	0.063*
C4	0.2163 (6)	1.1877 (4)	1.0883 (3)	0.0588 (11)
H4A	0.2090	1.2435	1.1419	0.071*
C3	0.1961 (6)	1.2515 (4)	0.9973 (3)	0.0615 (11)
H3A	0.1738	1.3484	0.9917	0.074*
C8	0.3276 (6)	0.6648 (4)	0.8695 (3)	0.0628 (11)
H8A	0.4205	0.6114	0.9162	0.075*
H8B	0.3787	0.6801	0.8119	0.075*

	U11	U22	U33	U12	U13	U23
Cl1	0.0894 (8)	0.0515 (6)	0.0475 (6)	0.0166 (5)	0.0280 (5)	0.0084 (4)
Cl2	0.0670 (7)	0.0524 (6)	0.0753 (7)	−0.0038 (5)	0.0119 (5)	−0.0149 (5)
N2	0.0488 (18)	0.0411 (16)	0.0452 (17)	0.0062 (14)	0.0111 (14)	0.0093 (12)
N1	0.0527 (19)	0.0459 (17)	0.0377 (15)	0.0017 (14)	0.0154 (14)	0.0019 (13)
C6	0.0319 (18)	0.0439 (18)	0.0407 (18)	0.0021 (15)	0.0104 (14)	0.0029 (14)
C1	0.0361 (18)	0.0403 (17)	0.0409 (18)	−0.0009 (15)	0.0105 (15)	−0.0002 (15)
C7	0.0383 (19)	0.0436 (19)	0.052 (2)	0.0025 (16)	0.0157 (16)	−0.0010 (16)
C5	0.050 (2)	0.071 (3)	0.0383 (19)	0.002 (2)	0.0099 (16)	−0.0059 (17)
C2	0.058 (2)	0.046 (2)	0.054 (2)	0.0001 (18)	0.0104 (19)	0.0072 (17)
C4	0.054 (2)	0.064 (3)	0.057 (2)	0.005 (2)	0.011 (2)	−0.022 (2)
C3	0.061 (3)	0.042 (2)	0.082 (3)	0.005 (2)	0.015 (2)	−0.013 (2)
C8	0.053 (2)	0.051 (2)	0.087 (3)	0.002 (2)	0.021 (2)	−0.016 (2)

C1—C6	1.381 (4)	C5—H5A	0.9300
C1—C2	1.389 (4)	C6—N2	1.385 (4)
C1—N1	1.391 (3)	C7—N2	1.320 (3)
C2—C3	1.372 (4)	C7—N1	1.322 (3)
C2—H2B	0.9300	C7—C8	1.477 (4)
C3—C4	1.395 (4)	C8—Cl2	1.781 (3)
C3—H3A	0.9300	C8—H8A	0.9700
C4—C5	1.367 (4)	C8—H8B	0.9700
C4—H4A	0.9300	N1—H1A	0.8600
C5—C6	1.392 (4)	N2—H2A	0.8600
C6—C1—C2	121.8 (3)	N2—C6—C5	132.0 (3)
C6—C1—N1	106.0 (2)	N2—C7—N1	109.3 (2)
C2—C1—N1	132.2 (3)	N2—C7—C8	125.5 (3)
C3—C2—C1	116.4 (3)	N1—C7—C8	125.2 (3)
C3—C2—H2B	121.8	C7—C8—Cl2	110.6 (2)
C1—C2—H2B	121.8	C7—C8—H8A	109.5
C2—C3—C4	121.8 (3)	Cl2—C8—H8A	109.5
C2—C3—H3A	119.1	C7—C8—H8B	109.5
C4—C3—H3A	119.1	Cl2—C8—H8B	109.5
C5—C4—C3	121.9 (3)	H8A—C8—H8B	108.1
C5—C4—H4A	119.1	C7—N1—C1	109.1 (2)
C3—C4—H4A	119.1	C7—N1—H1A	125.5
C4—C5—C6	116.5 (3)	C1—N1—H1A	125.5
C4—C5—H5A	121.7	C7—N2—C6	109.2 (2)
C6—C5—H5A	121.7	C7—N2—H2A	125.4
C1—C6—N2	106.4 (2)	C6—N2—H2A	125.4
C1—C6—C5	121.5 (3)
C6—C1—C2—C3	0.1 (5)	N2—C7—C8—Cl2	84.1 (4)
N1—C1—C2—C3	−178.5 (3)	N1—C7—C8—Cl2	−95.6 (3)
C1—C2—C3—C4	0.6 (5)	N2—C7—N1—C1	1.1 (3)
C2—C3—C4—C5	−0.7 (5)	C8—C7—N1—C1	−179.1 (3)
C3—C4—C5—C6	0.1 (5)	C6—C1—N1—C7	−0.3 (3)
C2—C1—C6—N2	−179.4 (3)	C2—C1—N1—C7	178.4 (3)
N1—C1—C6—N2	−0.5 (3)	N1—C7—N2—C6	−1.5 (3)
C2—C1—C6—C5	−0.7 (4)	C8—C7—N2—C6	178.8 (3)
N1—C1—C6—C5	178.2 (3)	C1—C6—N2—C7	1.2 (3)
C4—C5—C6—C1	0.6 (4)	C5—C6—N2—C7	−177.3 (3)
C4—C5—C6—N2	178.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.86	2.25	3.066 (2)	158
N2—H2A···Cl1	0.86	2.20	3.055 (2)	178

Group 1	Group 2	α /°	DCC /Å	τ /°
Cg1	Cg2i	1.43	3.768 (2)	21.88
Cg1	Cg2ii	1.43	3.551 (2)	12.47

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.86	2.25	3.066 (2)	158
N2—H2A⋯Cl1	0.86	2.20	3.055 (2)	178

Symmetry code: (i) .