1H-Benzimidazole-2(3H)-thione.

The asymmetric unit of the title compound, C(7)H(6)N(2)S, contains one half-mol-ecule; the C and S atoms of the C=S group lie on a crystallographic mirror plane. In the crystal structure, inter-molecular N-H⋯S hydrogen bonds link the mol-ecules.

Related literature

For a related structure, see: Mavrova et al. (2007 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C7H6N2S

M = 150.21

Monoclinic,

a = 4.915 (1) Å

b = 8.5590 (17) Å

c = 8.2920 (17) Å

β = 91.76 (3)°

V = 348.66 (12) Å3

Z = 2

Mo Kα radiation

μ = 0.38 mm−1

T = 294 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.896, T max = 0.963

903 measured reflections

813 independent reflections

647 reflections with I > 2σ(I)

R int = 0.044

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.152

S = 1.00

813 reflections

45 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ▶); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATOn class="Chemical">N (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809008058/hk2638sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008058/hk2638Isup2.hkl

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

C7H6N2S	F(000) = 156
Mr = 150.21	Dx = 1.431 Mg m−3
Monoclinic, P21/m	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yb	Cell parameters from 25 reflections
a = 4.915 (1) Å	θ = 10–14°
b = 8.5590 (17) Å	µ = 0.38 mm−1
c = 8.2920 (17) Å	T = 294 K
β = 91.76 (3)°	Block, colorless
V = 348.66 (12) Å3	0.30 × 0.20 × 0.10 mm
Z = 2

Enraf–Nonius CAD-4 diffractometer	647 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.044
graphite	θmax = 27.0°, θmin = 2.5°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = 0→10
Tmin = 0.896, Tmax = 0.963	l = −10→10
903 measured reflections	3 standard reflections every 120 min
813 independent reflections	intensity decay: 1%

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152	H-atom parameters constrained
S = 1.00	w = 1/[σ2(Fo2) + (0.1P)2 + 0.059P] where P = (Fo2 + 2Fc2)/3
813 reflections	(Δ/σ)max < 0.001
45 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.26 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
S	0.06322 (19)	0.2500	0.88609 (10)	0.0510 (3)
N	−0.2841 (4)	0.1239 (2)	1.1022 (2)	0.0465 (5)
H0A	−0.2505	0.0281	1.0783	0.056*
C1	−0.7826 (5)	0.1687 (4)	1.4250 (3)	0.0644 (7)
H1A	−0.8914	0.1154	1.4964	0.077*
C2	−0.6229 (5)	0.0844 (3)	1.3201 (3)	0.0561 (7)
H2A	−0.6243	−0.0242	1.3195	0.067*
C3	−0.4611 (4)	0.1684 (3)	1.2162 (3)	0.0437 (5)
C4	−0.1646 (7)	0.2500	1.0292 (4)	0.047

	U11	U22	U33	U12	U13	U23
S	0.0671 (6)	0.0270 (5)	0.0588 (6)	0.000	0.0015 (4)	0.000
N	0.0585 (11)	0.0227 (9)	0.0578 (12)	−0.0010 (8)	−0.0061 (9)	0.0009 (8)
C1	0.0621 (14)	0.0558 (17)	0.0755 (18)	−0.0084 (13)	0.0082 (13)	0.0065 (14)
C2	0.0681 (15)	0.0359 (13)	0.0640 (16)	−0.0047 (12)	−0.0032 (13)	0.0047 (11)
C3	0.0484 (11)	0.0302 (12)	0.0519 (13)	0.0009 (9)	−0.0094 (9)	−0.0003 (9)
C4	0.057	0.029	0.054	0.000	−0.019	0.000

S—C4	1.656 (4)	C1—H1A	0.9300
N—C3	1.359 (3)	C2—C3	1.390 (3)
N—C4	1.378 (3)	C2—H2A	0.9300
N—H0A	0.8600	C3—C3i	1.398 (4)
C1—C2	1.391 (4)	C4—Ni	1.378 (3)
C1—C1i	1.391 (6)
C3—N—C4	112.1 (2)	C1—C2—H2A	121.2
C3—N—H0A	123.9	N—C3—C2	132.6 (2)
C4—N—H0A	123.9	N—C3—C3i	106.27 (12)
C2—C1—C1i	121.24 (16)	C2—C3—C3i	121.11 (15)
C2—C1—H1A	119.4	N—C4—Ni	103.2 (3)
C1i—C1—H1A	119.4	N—C4—S	128.40 (15)
C3—C2—C1	117.6 (2)	Ni—C4—S	128.40 (15)
C3—C2—H2A	121.2
C1i—C1—C2—C3	0.6 (3)	C1—C2—C3—C3i	−0.6 (3)
C4—N—C3—C2	−179.1 (2)	C3—N—C4—Ni	−1.5 (3)
C4—N—C3—C3i	1.0 (2)	C3—N—C4—S	179.5 (2)
C1—C2—C3—N	179.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Sii	0.86	2.57	3.3798 (19)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯Si	0.86	2.57	3.3798 (19)	158

Symmetry code: (i) .