Acta Cryst. (2009). E65, o756 [ doi:10.1107/S1600536809008058 ]
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.
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.
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).
Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); 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 (Spek, 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
![[Figure 1]](./hk2638fig1thm.gif)
| Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
![[Figure 2]](./hk2638fig2thm.gif)
| Fig. 2. A partial packing diagram. Hydrogen bonds are shown as dashed lines. |
| 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 |
| C7H6N2S | V = 348.66 (12) Å3 |
| Mr = 150.21 | Z = 2 |
| Monoclinic, P21/m | Mo Kα radiation |
| a = 4.915 (1) Å | µ = 0.38 mm−1 |
| b = 8.5590 (17) Å | T = 294 K |
| c = 8.2920 (17) Å | 0.30 × 0.20 × 0.10 mm |
| β = 91.76 (3)° |
| Enraf–Nonius CAD-4 diffractometer | 647 reflections with I > 2σ(I) |
| Absorption correction: ψ scan (North et al., 1968) | Rint = 0.044 |
| Tmin = 0.896, Tmax = 0.963 | θmax = 27.0° |
| 903 measured reflections | 3 standard reflections every 120 min |
| 813 independent reflections | intensity decay: 1% |
| R[F2 > 2σ(F2)] = 0.049 | H-atom parameters constrained |
| wR(F2) = 0.152 | Δρmax = 0.37 e Å−3 |
| S = 1.00 | Δρmin = −0.26 e Å−3 |
| 813 reflections | Absolute structure: ? |
| 45 parameters | Flack parameter: ? |
| 0 restraints | Rogers parameter: ? |
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) |
| Symmetry codes: (i) x, −y+1/2, z. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N—H0A···Sii | 0.86 | 2.57 | 3.3798 (19) | 158 |
| Symmetry codes: (ii) −x, y−1/2, −z+2. |
| D—H···A | D—H | H···A | D···A | D—H···A |
| N—H0A···Si | 0.86 | 2.57 | 3.3798 (19) | 158 |
| Symmetry codes: (i) −x, y−1/2, −z+2. |
The authors thank the Center of Testing and Analysis, Nanjing University, for support.
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.
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.
Spek, A. L. (2009). Acta Cryst. D65, 148–155.
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.