1-Methyl-1H-benzimidazole-2(3H)-thione.

The title compound, C(8)H(8)N(2)S, was prepared by the condensation of N-methyl-1,2-phenyl-enediamine and carbon disulfide. The crystal structure is stabilized by a C-H⋯π inter-action between a benzene H atom and the benzene ring of a neighbouring mol-ecule, and by inter-molecular N-H⋯S inter-actions.

Related literature

For related literature, see: Baily et al. (1996 ▶); Koch (2001 ▶); Namgun et al. (2001 ▶); Schuster et al. (1990 ▶); Patel & Chedekel (1984 ▶).

Experimental

Crystal data

C8H8N2S

M = 164.22

Monoclinic,

a = 9.997 (4) Å

b = 5.8140 (7) Å

c = 13.703 (4) Å

β = 94.05 (3)°

V = 794.5 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 293 (2) K

0.20 × 0.10 × 0.02 mm

Data collection

Oxford Diffraction Xcalibur2 CCD diffractometer

Absorption correction: analytical (CrysAlis RED; Oxford Diffraction; 2004 ▶; Clark & Reid, 1995 ▶) T min = 0.929, T max = 0.967

7237 measured reflections

962 independent reflections

855 reflections with I > 2σ(I)

R int = 0.023

θmax = 23.1°

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.077

S = 1.09

962 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2004 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: PLATON.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808015043/lx2055sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808015043/lx2055Isup2.hkl

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

C8H8N2S	F000 = 344
Mr = 164.22	Dx = 1.373 Mg m−3
Monoclinic, P21/n	Melting point: 402 K
Hall symbol: -P_2yn	Mo Kα radiation λ = 0.71073 Å
a = 9.997 (4) Å	Cell parameters from 5701 reflections
b = 5.8140 (7) Å	θ = 3.7–23.1º
c = 13.703 (4) Å	µ = 0.34 mm−1
β = 94.05 (3)º	T = 293 (2) K
V = 794.5 (4) Å3	Block, colourless
Z = 4	0.20 × 0.10 × 0.02 mm

Oxford Diffraction Xcalibur2 CCD diffractometer	962 independent reflections
Radiation source: Enhance (Mo) X-ray Source	855 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.023
Detector resolution: 10.0 pixels mm-1	θmax = 23.1º
T = 293(2) K	θmin = 3.8º
ω scans	h = −10→11
Absorption correction: analytical(CrysAlis RED; Oxford Diffraction; 2004; Clark & Reid, 1995)	k = −6→6
Tmin = 0.929, Tmax = 0.967	l = −14→14
7237 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.078	w = 1/[σ2(Fo2) + (0.0353P)2 + 0.4983P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max = 0.001
962 reflections	Δρmax = 0.21 e Å−3
101 parameters	Δρmin = −0.19 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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 > 2sigma(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
S	0.73449 (6)	0.62833 (10)	0.62836 (4)	0.0475 (3)
N1	0.52959 (17)	0.3736 (3)	0.69273 (12)	0.0345 (5)
N2	0.57646 (17)	0.6789 (3)	0.78071 (12)	0.0380 (5)
H2	0.6119	0.8071	0.8004	0.046*
C1	0.6119 (2)	0.5599 (4)	0.70145 (15)	0.0359 (6)
C2	0.4462 (2)	0.3690 (3)	0.77058 (15)	0.0323 (5)
C3	0.3528 (2)	0.2095 (4)	0.79703 (16)	0.0399 (6)
H3	0.3342	0.0773	0.7603	0.048*
C4	0.2882 (2)	0.2566 (4)	0.88107 (17)	0.0461 (6)
H4	0.2255	0.1524	0.9017	0.055*
C5	0.3145 (2)	0.4548 (4)	0.93499 (17)	0.0466 (6)
H5	0.2684	0.4812	0.9906	0.056*
C6	0.4079 (2)	0.6150 (4)	0.90824 (16)	0.0412 (6)
H6	0.4246	0.7492	0.9440	0.049*
C7	0.4752 (2)	0.5656 (4)	0.82572 (15)	0.0330 (5)
C8	0.5331 (3)	0.1997 (4)	0.61682 (17)	0.0518 (7)
H8A	0.5508	0.2717	0.5560	0.078*
H8B	0.4482	0.1221	0.6098	0.078*
H8C	0.6026	0.0904	0.6345	0.078*

	U11	U22	U33	U12	U13	U23
S	0.0446 (4)	0.0454 (4)	0.0547 (4)	0.0026 (3)	0.0184 (3)	0.0102 (3)
N1	0.0345 (10)	0.0313 (10)	0.0384 (10)	0.0019 (8)	0.0071 (8)	−0.0027 (8)
N2	0.0379 (11)	0.0323 (10)	0.0443 (11)	−0.0042 (8)	0.0064 (9)	−0.0040 (9)
C1	0.0350 (12)	0.0332 (12)	0.0396 (13)	0.0068 (11)	0.0026 (10)	0.0050 (10)
C2	0.0283 (11)	0.0339 (13)	0.0348 (12)	0.0062 (10)	0.0024 (9)	0.0023 (10)
C3	0.0365 (12)	0.0356 (13)	0.0478 (14)	−0.0024 (11)	0.0043 (11)	−0.0016 (11)
C4	0.0380 (13)	0.0483 (16)	0.0529 (15)	−0.0053 (11)	0.0094 (12)	0.0080 (13)
C5	0.0425 (13)	0.0601 (16)	0.0383 (13)	0.0015 (13)	0.0104 (11)	0.0021 (12)
C6	0.0423 (13)	0.0431 (14)	0.0380 (13)	0.0040 (11)	0.0017 (10)	−0.0060 (11)
C7	0.0302 (12)	0.0330 (12)	0.0358 (12)	0.0021 (10)	0.0019 (10)	0.0020 (10)
C8	0.0536 (15)	0.0493 (15)	0.0542 (15)	−0.0015 (13)	0.0150 (12)	−0.0150 (13)

S—C1	1.684 (2)	C3—H3	0.9300
N1—C1	1.361 (3)	C4—C5	1.384 (3)
N1—C2	1.400 (3)	C4—H4	0.9300
N1—C8	1.453 (3)	C5—C6	1.386 (3)
N2—C1	1.356 (3)	C5—H5	0.9300
N2—C7	1.389 (3)	C6—C7	1.386 (3)
N2—H2	0.8600	C6—H6	0.9300
C2—C3	1.383 (3)	C8—H8A	0.9600
C2—C7	1.389 (3)	C8—H8B	0.9600
C3—C4	1.387 (3)	C8—H8C	0.9600
C1—N1—C2	109.71 (17)	C3—C4—H4	119.2
C1—N1—C8	124.88 (18)	C4—C5—C6	121.6 (2)
C2—N1—C8	125.34 (18)	C4—C5—H5	119.2
C1—N2—C7	110.71 (18)	C6—C5—H5	119.2
C1—N2—H2	124.6	C7—C6—C5	116.8 (2)
C7—N2—H2	124.6	C7—C6—H6	121.6
N2—C1—N1	106.62 (18)	C5—C6—H6	121.6
N2—C1—S	126.72 (18)	C6—C7—N2	132.5 (2)
N1—C1—S	126.65 (17)	C6—C7—C2	121.3 (2)
C3—C2—C7	121.86 (19)	N2—C7—C2	106.21 (17)
C3—C2—N1	131.46 (19)	N1—C8—H8A	109.5
C7—C2—N1	106.66 (17)	N1—C8—H8B	109.5
C2—C3—C4	116.6 (2)	H8A—C8—H8B	109.5
C2—C3—H3	121.7	N1—C8—H8C	109.5
C4—C3—H3	121.7	H8A—C8—H8C	109.5
C5—C4—C3	121.7 (2)	H8B—C8—H8C	109.5
C5—C4—H4	119.2
C7—N2—C1—N1	2.4 (2)	C2—C3—C4—C5	0.9 (3)
C7—N2—C1—S	−177.28 (16)	C3—C4—C5—C6	−0.7 (4)
C2—N1—C1—N2	−3.2 (2)	C4—C5—C6—C7	−1.0 (3)
C8—N1—C1—N2	179.79 (19)	C5—C6—C7—N2	−177.1 (2)
C2—N1—C1—S	176.50 (15)	C5—C6—C7—C2	2.4 (3)
C8—N1—C1—S	−0.5 (3)	C1—N2—C7—C6	178.9 (2)
C1—N1—C2—C3	−175.6 (2)	C1—N2—C7—C2	−0.7 (2)
C8—N1—C2—C3	1.4 (3)	C3—C2—C7—C6	−2.3 (3)
C1—N1—C2—C7	2.8 (2)	N1—C2—C7—C6	179.11 (19)
C8—N1—C2—C7	179.79 (19)	C3—C2—C7—N2	177.32 (19)
C7—C2—C3—C4	0.6 (3)	N1—C2—C7—N2	−1.2 (2)
N1—C2—C3—C4	178.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Si	0.86	2.57	3.408 (2)	166
C3—H3···Cgii	0.93	2.74	3.464 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯Si	0.86	2.57	3.408 (2)	166
C3—H3⋯Cgii	0.93	2.74	3.464 (3)	136

Symmetry codes: (i) ; (ii) . Cg is the centroid of the C2–C7 ring.