2-Chloro-methyl-1-methyl-1,3-benzimidazole.

The title compound, C(9)H(9)ClN(2), was prepared from the reaction of N-methyl-benzene-1,2-diamine and 2-chloro-acetic acid in boiling 6 M hydro-chloric acid. The benzimidazole unit is approximately planar, the largest deviation from the mean plane being 0.008 (1) Å. The Cl atom is displaced by 1.667 (2) Å from this plane. The methyl group is statistically disordered with equal occupancy.

Related literature

For the biological activity of benzimidazoles, see: Refaat (2010 ▶); Laryea et al. (2010 ▶); Horton et al. (2003 ▶); Ries et al. (2003 ▶); Spasov et al. (1999 ▶); Matsui et al. (1994 ▶); Porcari et al. (1998 ▶); Rath et al. (1997 ▶); Migawa et al. (1998 ▶). For a description of the Cambridge Structural Database, see: Allen (2002 ▶).

Experimental

Crystal data

C9H9ClN2

M = 180.63

Triclinic,

a = 6.607 (2) Å

b = 8.168 (2) Å

c = 8.925 (3) Å

α = 84.566 (3)°

β = 79.682 (4)°

γ = 68.134 (4)°

V = 439.6 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 296 K

0.37 × 0.29 × 0.18 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2002 ▶) T min = 0.874, T max = 0.937

2191 measured reflections

1523 independent reflections

1361 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.122

S = 1.06

1523 reflections

109 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.32 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶) and ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811028376/dn2705sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028376/dn2705Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028376/dn2705Isup3.cml

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

C9H9ClN2	Z = 2
Mr = 180.63	F(000) = 188
Triclinic, P1	Dx = 1.365 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.607 (2) Å	Cell parameters from 2191 reflections
b = 8.168 (2) Å	θ = 2.3–25.1°
c = 8.925 (3) Å	µ = 0.38 mm−1
α = 84.566 (3)°	T = 296 K
β = 79.682 (4)°	Block, white
γ = 68.134 (4)°	0.37 × 0.29 × 0.18 mm
V = 439.6 (2) Å3

Bruker SMART APEX CCD diffractometer	1523 independent reflections
Radiation source: fine-focus sealed tube	1361 reflections with I > 2σ(I)
graphite	Rint = 0.018
φ and ω scans	θmax = 25.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2002)	h = −7→5
Tmin = 0.874, Tmax = 0.937	k = −9→9
2191 measured reflections	l = −10→10

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.122	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0552P)2 + 0.1656P] where P = (Fo2 + 2Fc2)/3
1523 reflections	(Δ/σ)max < 0.001
109 parameters	Δρmax = 0.20 e Å−3
0 restraints	Δρmin = −0.32 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
C1	0.2259 (4)	0.4372 (3)	0.6995 (2)	0.0610 (6)
H1A	0.3424	0.4781	0.7109	0.073*
H1B	0.0985	0.5393	0.6790	0.073*
C2	0.1665 (3)	0.3458 (2)	0.8432 (2)	0.0498 (5)
C3	−0.2214 (4)	0.3954 (3)	0.8004 (3)	0.0666 (6)
H3A	−0.3405	0.3638	0.8563	0.100*	0.50
H3B	−0.1788	0.3444	0.7017	0.100*	0.50
H3C	−0.2683	0.5215	0.7888	0.100*	0.50
H3D	−0.1846	0.4560	0.7082	0.100*	0.50
H3E	−0.3463	0.4754	0.8628	0.100*	0.50
H3F	−0.2568	0.2983	0.7757	0.100*	0.50
C4	−0.0294 (3)	0.2393 (2)	1.0212 (2)	0.0488 (5)
C5	−0.1859 (4)	0.1843 (3)	1.1144 (3)	0.0600 (6)
H5	−0.3242	0.2069	1.0885	0.072*
C6	−0.1250 (4)	0.0947 (3)	1.2471 (3)	0.0675 (6)
H6	−0.2258	0.0574	1.3137	0.081*
C7	0.0842 (4)	0.0581 (3)	1.2848 (3)	0.0673 (6)
H7	0.1198	−0.0041	1.3751	0.081*
C8	0.2384 (4)	0.1119 (3)	1.1915 (2)	0.0605 (6)
H8	0.3773	0.0871	1.2173	0.073*
C9	0.1803 (3)	0.2046 (2)	1.0572 (2)	0.0495 (5)
Cl1	0.31643 (17)	0.29247 (10)	0.54306 (8)	0.1088 (4)
N1	0.3008 (3)	0.2749 (2)	0.94299 (19)	0.0535 (4)
N2	−0.0342 (3)	0.3294 (2)	0.88264 (18)	0.0498 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0686 (13)	0.0587 (12)	0.0545 (12)	−0.0238 (11)	−0.0075 (10)	0.0029 (10)
C2	0.0509 (11)	0.0472 (10)	0.0489 (11)	−0.0161 (8)	−0.0037 (8)	−0.0048 (8)
C3	0.0599 (13)	0.0680 (14)	0.0736 (15)	−0.0195 (11)	−0.0252 (11)	0.0030 (11)
C4	0.0505 (10)	0.0436 (10)	0.0495 (11)	−0.0146 (8)	−0.0031 (8)	−0.0077 (8)
C5	0.0550 (12)	0.0568 (12)	0.0676 (14)	−0.0235 (10)	0.0018 (10)	−0.0068 (10)
C6	0.0741 (15)	0.0634 (13)	0.0630 (14)	−0.0314 (12)	0.0101 (11)	−0.0041 (11)
C7	0.0840 (16)	0.0602 (13)	0.0512 (12)	−0.0235 (12)	−0.0033 (11)	0.0048 (10)
C8	0.0609 (13)	0.0639 (13)	0.0540 (12)	−0.0198 (10)	−0.0100 (10)	0.0006 (10)
C9	0.0513 (11)	0.0483 (10)	0.0474 (10)	−0.0173 (9)	−0.0040 (8)	−0.0042 (8)
Cl1	0.1675 (9)	0.0837 (5)	0.0523 (4)	−0.0326 (5)	0.0147 (4)	−0.0069 (3)
N1	0.0494 (9)	0.0588 (10)	0.0518 (10)	−0.0203 (8)	−0.0065 (7)	0.0006 (8)
N2	0.0465 (9)	0.0509 (9)	0.0520 (9)	−0.0170 (7)	−0.0082 (7)	−0.0028 (7)

C1—C2	1.488 (3)	C4—N2	1.377 (3)
C1—Cl1	1.786 (2)	C4—C5	1.389 (3)
C1—H1A	0.9700	C4—C9	1.398 (3)
C1—H1B	0.9700	C5—C6	1.373 (3)
C2—N1	1.310 (3)	C5—H5	0.9300
C2—N2	1.363 (3)	C6—C7	1.397 (4)
C3—N2	1.453 (3)	C6—H6	0.9300
C3—H3A	0.9600	C7—C8	1.373 (3)
C3—H3B	0.9600	C7—H7	0.9300
C3—H3C	0.9600	C8—C9	1.390 (3)
C3—H3D	0.9600	C8—H8	0.9300
C3—H3E	0.9600	C9—N1	1.393 (3)
C3—H3F	0.9600
C2—C1—Cl1	110.86 (15)	H3B—C3—H3F	56.3
C2—C1—H1A	109.5	H3C—C3—H3F	141.1
Cl1—C1—H1A	109.5	H3D—C3—H3F	109.5
C2—C1—H1B	109.5	H3E—C3—H3F	109.5
Cl1—C1—H1B	109.5	N2—C4—C5	131.59 (19)
H1A—C1—H1B	108.1	N2—C4—C9	105.69 (17)
N1—C2—N2	114.14 (18)	C5—C4—C9	122.71 (19)
N1—C2—C1	123.36 (19)	C6—C5—C4	116.3 (2)
N2—C2—C1	122.49 (18)	C6—C5—H5	121.9
N2—C3—H3A	109.5	C4—C5—H5	121.9
N2—C3—H3B	109.5	C5—C6—C7	121.9 (2)
H3A—C3—H3B	109.5	C5—C6—H6	119.1
N2—C3—H3C	109.5	C7—C6—H6	119.1
H3A—C3—H3C	109.5	C8—C7—C6	121.5 (2)
H3B—C3—H3C	109.5	C8—C7—H7	119.3
N2—C3—H3D	109.5	C6—C7—H7	119.3
H3A—C3—H3D	141.1	C7—C8—C9	117.9 (2)
H3B—C3—H3D	56.3	C7—C8—H8	121.1
H3C—C3—H3D	56.3	C9—C8—H8	121.1
N2—C3—H3E	109.5	C8—C9—N1	130.36 (19)
H3A—C3—H3E	56.3	C8—C9—C4	119.77 (19)
H3B—C3—H3E	141.1	N1—C9—C4	109.87 (17)
H3C—C3—H3E	56.3	C2—N1—C9	104.17 (16)
H3D—C3—H3E	109.5	C2—N2—C4	106.13 (16)
N2—C3—H3F	109.5	C2—N2—C3	128.34 (18)
H3A—C3—H3F	56.3	C4—N2—C3	125.52 (17)