2-Methyl-benzimidazolium thio-cyanate.

In the crystal structure of the title compound, C(8)H(9)N(2) (+)·SCN(-), the nearly planar 2-methyl-benzimidazolium cation [r.m.s. deviation = 0.0123 (4) Å] is perpendicular to a mirror plane and the methyl H atoms are disordered about the mirror plane with equal occupancies. The thio-cyanate anion also lies on a mirror plane. N-H⋯N hydrogen bonds link the components into an infinite chain along the b axis.

Related literature

For related structures, see: Bhattacharya et al. (2004 ▶); Ding et al. (2004 ▶); Shaker et al. (2010 ▶); Huang et al. (2006 ▶). For the application of benzimidazole derivatives in crystal engineering, see: Cai et al. (2002 ▶). For the biological properties of benzimidazole derivatives, see: Refaat (2010 ▶); Ansari & Lal (2009 ▶).

Experimental

Crystal data

C8H9N2 +·SCN−

M = 191.25

Orthorhombic,

a = 9.879 (2) Å

b = 7.2157 (15) Å

c = 12.890 (3) Å

V = 918.9 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.31 mm−1

T = 100 K

0.40 × 0.29 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.888, T max = 0.956

10495 measured reflections

1133 independent reflections

1000 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.090

S = 1.01

1133 reflections

71 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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: SHELXL97 and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810042145/is2616sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042145/is2616Isup2.hkl

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

C8H9N2+·SCN−	F(000) = 400
Mr = 191.25	Dx = 1.382 Mg m−3
Orthorhombic, Pnma	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2n	Cell parameters from 4285 reflections
a = 9.879 (2) Å	θ = 2.6–30.3°
b = 7.2157 (15) Å	µ = 0.31 mm−1
c = 12.890 (3) Å	T = 100 K
V = 918.9 (3) Å3	Block, colorless
Z = 4	0.40 × 0.29 × 0.15 mm

Bruker APEXII CCD diffractometer	1133 independent reflections
Radiation source: fine-focus sealed tube	1000 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 27.5°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.888, Tmax = 0.956	k = −9→9
10495 measured reflections	l = −16→16

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0395P)2 + 0.9286P] where P = (Fo2 + 2Fc2)/3
1133 reflections	(Δ/σ)max < 0.001
71 parameters	Δρmax = 0.39 e Å−3
1 restraint	Δρmin = −0.28 e Å−3

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	Occ. (<1)
S1	−0.11964 (6)	0.2500	0.31732 (5)	0.02094 (18)
N1	0.15210 (19)	0.2500	0.37930 (15)	0.0193 (4)
C1	0.0383 (2)	0.2500	0.35335 (17)	0.0162 (4)
H2	0.2584 (17)	0.485 (2)	0.3813 (13)	0.019*
N2	0.28838 (12)	0.60009 (17)	0.38143 (10)	0.0155 (3)
C2	0.0609 (2)	0.7500	0.38575 (17)	0.0191 (5)
H2A	0.0277	0.8779	0.3825	0.029*	0.50
H2B	0.0299	0.6922	0.4503	0.029*	0.50
H2BA	0.0258	0.6800	0.3264	0.029*	0.50
C3	0.2103 (2)	0.7500	0.38283 (15)	0.0156 (4)
C4	0.42343 (15)	0.6534 (2)	0.37939 (11)	0.0148 (3)
C5	0.54317 (15)	0.5525 (2)	0.37848 (11)	0.0179 (3)
H5	0.5432	0.4209	0.3774	0.022*
C6	0.66199 (15)	0.6529 (2)	0.37921 (11)	0.0189 (3)
H6	0.7460	0.5887	0.3797	0.023*

	U11	U22	U33	U12	U13	U23
S1	0.0159 (3)	0.0182 (3)	0.0287 (3)	0.000	−0.0020 (2)	0.000
N1	0.0179 (9)	0.0140 (9)	0.0260 (10)	0.000	0.0024 (7)	0.000
C1	0.0200 (10)	0.0105 (9)	0.0182 (10)	0.000	0.0034 (8)	0.000
N2	0.0169 (6)	0.0104 (6)	0.0191 (6)	−0.0018 (5)	0.0000 (5)	0.0004 (5)
C2	0.0170 (10)	0.0192 (11)	0.0211 (11)	0.000	0.0015 (8)	0.000
C3	0.0193 (10)	0.0151 (10)	0.0126 (9)	0.000	−0.0012 (8)	0.000
C4	0.0168 (7)	0.0141 (7)	0.0135 (6)	−0.0007 (6)	−0.0004 (5)	0.0004 (5)
C5	0.0215 (7)	0.0126 (7)	0.0197 (7)	0.0023 (6)	−0.0015 (6)	−0.0003 (6)
C6	0.0175 (7)	0.0200 (8)	0.0193 (7)	0.0026 (6)	−0.0007 (6)	0.0001 (6)

S1—C1	1.628 (2)	C2—H2BA	0.9800
N1—C1	1.173 (3)	C4—C5	1.389 (2)
N2—C3	1.3289 (18)	C4—C4i	1.394 (3)
N2—C4	1.3888 (19)	C5—C6	1.379 (2)
N2—H2	0.881 (15)	C5—H5	0.9500
C2—C3	1.477 (3)	C6—C6i	1.401 (3)
C2—H2A	0.9800	C6—H6	0.9500
C2—H2B	0.9800
N1—C1—S1	180.0 (2)	N2—C3—C2	125.52 (9)
C3—N2—C4	109.44 (13)	N2—C4—C5	132.32 (14)
C3—N2—H2	124.8 (12)	N2—C4—C4i	106.08 (8)
C4—N2—H2	125.7 (12)	C5—C4—C4i	121.60 (9)
C3—C2—H2A	109.5	C6—C5—C4	116.72 (15)
C3—C2—H2B	109.5	C6—C5—H5	121.6
H2A—C2—H2B	109.5	C4—C5—H5	121.6
C3—C2—H2BA	109.5	C5—C6—C6i	121.67 (9)
H2A—C2—H2BA	109.5	C5—C6—H6	119.2
H2B—C2—H2BA	109.5	C6i—C6—H6	119.2
N2—C3—N2i	108.97 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···N1	0.88 (2)	2.00 (2)	2.8627 (16)	168 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯N1	0.88 (2)	2.00 (2)	2.8627 (16)	168 (2)