PMCCPMCCPMCC

Search tips
Search criteria 

Advanced

 
Logo of actaeInternational Union of Crystallographysearchopen accessarticle submissionjournal home pagethis article
 
Acta Crystallogr Sect E Struct Rep Online. 2009 April 1; 65(Pt 4): o756.
Published online 2009 March 14. doi:  10.1107/S1600536809008058
PMCID: PMC2968823

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

Abstract

The asymmetric unit of the title compound, C7H6N2S, contains one half-mol­ecule; the C and S atoms of the C=S group lie on a crystallographic mirror plane. In the crystal structure, inter­molecular N—H(...)S hydrogen bonds link the mol­ecules.

Related literature

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

An external file that holds a picture, illustration, etc.
Object name is e-65-0o756-scheme1.jpg

Experimental

Crystal data

  • C7H6N2S
  • M r = 150.21
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o756-efi1.jpg
  • 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 [triangle]) 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 [triangle]); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 [triangle]) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

The authors thank the Center of Testing and Analysis, Nanjing University, for support.

supplementary crystallographic information

Comment

It is a kind of secondary age inhibitor, and could reinforce the effect combined with DNP AP and other nonpolluting age inhibitors. It disperses easily in rubber, and the color does not change under sun exposure. Its pollution capacity is limited. 2-Mercaptobenzimidiazole is a new kind of anti-leprosy drugs, and its toxicity is lower than sulphone drugs. It should not be used in the patients to which can not be given sulphone drugs. We report herein the crystal structure of the title compound.

The asymmetric unit of the title compound (Fig. 1) contains one-half molecule, in which a mirror plane passes through S and C4 atoms. The bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal structure, intermolecular N-H···S hydrogen bonds (Table 1) link the molecules (Fig. 2), in which they may be effective in the stabilization of the structure.

Experimental

For the preparation of the title comppund, 1,2-diaminobenzene (0.019 mol) and water (3 ml) were added to a solution of sodium hydroxide (0.022 mol) in ethanol (20 ml) and carbon disulfide (0.022 mol). The mixture was heated under reflux for 3 h. Charcoal was added cautiously and removed by filtration after the mixture has been refluxed for 10 min more. The filtrate was heated to 377 K and quenched with warm water (377 K, 20 ml), and then acetic acid (9 ml) was added by stirring. The product was separated and after cooling in refrigerator for 3 h the crystallization was completed (Mavrova et al., 2007). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethanol solution after two weeks.

Refinement

H atoms were positioned geometrically, with N-H = 0.86 Å (for NH) and C-H = 0.93 Å for aromatic H and constrained to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C,N).

Figures

Fig. 1.
The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
Fig. 2.
A partial packing diagram. Hydrogen bonds are shown as dashed lines.

Crystal data

C7H6N2SF(000) = 156
Mr = 150.21Dx = 1.431 Mg m3
Monoclinic, P21/mMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybCell parameters from 25 reflections
a = 4.915 (1) Åθ = 10–14°
b = 8.5590 (17) ŵ = 0.38 mm1
c = 8.2920 (17) ÅT = 294 K
β = 91.76 (3)°Block, colorless
V = 348.66 (12) Å30.30 × 0.20 × 0.10 mm
Z = 2

Data collection

Enraf–Nonius CAD-4 diffractometer647 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.044
graphiteθmax = 27.0°, θmin = 2.5°
ω/2θ scansh = 0→6
Absorption correction: ψ scan (North et al., 1968)k = 0→10
Tmin = 0.896, Tmax = 0.963l = −10→10
903 measured reflections3 standard reflections every 120 min
813 independent reflections intensity decay: 1%

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.152H-atom parameters constrained
S = 1.00w = 1/[σ2(Fo2) + (0.1P)2 + 0.059P] where P = (Fo2 + 2Fc2)/3
813 reflections(Δ/σ)max < 0.001
45 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = −0.26 e Å3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S0.06322 (19)0.25000.88609 (10)0.0510 (3)
N−0.2841 (4)0.1239 (2)1.1022 (2)0.0465 (5)
H0A−0.25050.02811.07830.056*
C1−0.7826 (5)0.1687 (4)1.4250 (3)0.0644 (7)
H1A−0.89140.11541.49640.077*
C2−0.6229 (5)0.0844 (3)1.3201 (3)0.0561 (7)
H2A−0.6243−0.02421.31950.067*
C3−0.4611 (4)0.1684 (3)1.2162 (3)0.0437 (5)
C4−0.1646 (7)0.25001.0292 (4)0.047

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S0.0671 (6)0.0270 (5)0.0588 (6)0.0000.0015 (4)0.000
N0.0585 (11)0.0227 (9)0.0578 (12)−0.0010 (8)−0.0061 (9)0.0009 (8)
C10.0621 (14)0.0558 (17)0.0755 (18)−0.0084 (13)0.0082 (13)0.0065 (14)
C20.0681 (15)0.0359 (13)0.0640 (16)−0.0047 (12)−0.0032 (13)0.0047 (11)
C30.0484 (11)0.0302 (12)0.0519 (13)0.0009 (9)−0.0094 (9)−0.0003 (9)
C40.0570.0290.0540.000−0.0190.000

Geometric parameters (Å, °)

S—C41.656 (4)C1—H1A0.9300
N—C31.359 (3)C2—C31.390 (3)
N—C41.378 (3)C2—H2A0.9300
N—H0A0.8600C3—C3i1.398 (4)
C1—C21.391 (4)C4—Ni1.378 (3)
C1—C1i1.391 (6)
C3—N—C4112.1 (2)C1—C2—H2A121.2
C3—N—H0A123.9N—C3—C2132.6 (2)
C4—N—H0A123.9N—C3—C3i106.27 (12)
C2—C1—C1i121.24 (16)C2—C3—C3i121.11 (15)
C2—C1—H1A119.4N—C4—Ni103.2 (3)
C1i—C1—H1A119.4N—C4—S128.40 (15)
C3—C2—C1117.6 (2)Ni—C4—S128.40 (15)
C3—C2—H2A121.2
C1i—C1—C2—C30.6 (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—C3i1.0 (2)C3—N—C4—S179.5 (2)
C1—C2—C3—N179.5 (2)

Symmetry codes: (i) x, −y+1/2, z.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N—H0A···Sii0.862.573.3798 (19)158

Symmetry codes: (ii) −x, y−1/2, −z+2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HK2638).

References

  • Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.
  • Enraf–Nonius (1989). CAD-4 Software Enraf–Nonius, Delft, The Netherlands.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Harms, K. & Wocadlo, S. (1995). XCAD4 University of Marburg, Germany.
  • Mavrova, A. Ts., Denkova, P., Tsenov, Y. A., Anichina, K. K. & Vutchev, D. I. (2007). Bioorg. Med. Chem 15, 6291–6297. [PubMed]
  • North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography