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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o247.
Published online 2007 December 12. doi:  10.1107/S1600536807065452
PMCID: PMC2915304

Bis(4H-1,2,4-triazol-3-yl)disulfane

Abstract

The title compound, C4H4N6S2, was synthesized by the reaction of 3-mercapto-1H-1,2,4-triazole with sodium hydrox­ide in ethanol. The mol­ecule possesses a crystallographically imposed twofold axis. Inter­molecular N—H(...)N hydrogen bonds link the mol­ecules into chains along the c axis.

Related literature

For related literature, see: De Luca (2006 [triangle]); Di Santo, Tafi, Costi, Botta, Artico, Corelli, Forte, Caporuscio, Angiolella & Palamara (2005 [triangle]); Fringuelli et al. (2005 [triangle]); Menozzi et al. (2004 [triangle]).

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Object name is e-64-0o247-scheme1.jpg

Experimental

Crystal data

  • C4H4N6S2
  • M r = 200.25
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o247-efi2.jpg
  • a = 14.052 (3) Å
  • b = 6.4044 (13) Å
  • c = 9.928 (2) Å
  • β = 122.18 (3)°
  • V = 756.2 (4) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.65 mm−1
  • T = 293 (2) K
  • 0.12 × 0.09 × 0.06 mm

Data collection

  • Rigaku R-AXIS RAPID IP diffractometer
  • Absorption correction: multi-scan (ABSCOR; Higashi, 1995 [triangle]) T min = 0.932, T max = 0.962
  • 3518 measured reflections
  • 859 independent reflections
  • 742 reflections with I > 2σ(I)
  • R int = 0.035

Refinement

  • R[F 2 > 2σ(F 2)] = 0.029
  • wR(F 2) = 0.081
  • S = 1.09
  • 859 reflections
  • 63 parameters
  • All H-atom parameters refined
  • Δρmax = 0.25 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 [triangle]); cell refinement: RAPID-AUTO (Rigaku, 1998 [triangle]); data reduction: RAPID-AUTO (Rigaku, 1998 [triangle]); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 [triangle]); molecular graphics: SHELXTL/PC (Sheldrick, 1993 [triangle]); software used to prepare material for publication: SHELXL97 (Sheldrick,1997 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065452/rz2177sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065452/rz2177Isup2.hkl

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

Acknowledgments

This work was supported financially by the Natural Science Project of Jinggangshan University (JZ0731).

supplementary crystallographic information

Comment

It is well known that derivatives of pyrazole, imidazole, triazole, tetrazole and indole exhibit extensive biological activities (De Luca, 2006; Fringuelli et al., 2005; Di Santo et al., 2005; Menozzi et al., 2004). In a search for more efficient antibacterial medicines, we have synthesized a new azole derivative and its crystal structure is reported here.

In the molecule of the title compound (Fig. 1), which possesses a crystallographically imposed twofold axis, the torsion angles C1—S1—S1i—C1i and S1i—S1—C1—N3 are 83.69 (8) and -93.69 (13)°, respectively [symmetry code: (i) -x, y, -0.5 - z]. The dihedral angle formed by the triazole rings is 21.80 (7)°. In the crystal structure (Fig. 2 and 3), molecules are linked by N—H···N hydrogen bonding interactions (Table 1) to form stepped chains running parallel to the c axis.

Experimental

3-Mercapto-1H-1,2,4-triazole (0.025 mol, 5.05 g) and sodium hydroxide (0.025 mol, 1.01 g) were dissolved in ethanol (15 ml). The mixture was refluxed at 353 K for five hours, cooled to room temperature, acidified with HCl (12 M) and filtered. Colourless crystal of the title compound were obtained on slow evaporation of the solvent after several days at room temperature.

Refinement

All H atoms were located in a difference Fourier map and refined isotropically.

Figures

Fig. 1.
The molecular structure of the title compound showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry code: (i) -x, y, -z - 1/2]
Fig. 2.
The chain of hydrogen-bonded molecules running along the c axis. Hydrogen bonding interactions are shown as red dashed lines.
Fig. 3.
Packing diagram of the title compound viewed along the c axis.

Crystal data

C4H4N6S2F000 = 408
Mr = 200.25Dx = 1.759 Mg m3
Monoclinic, C2/cMo Kα radiation λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 25 reflections
a = 14.052 (3) Åθ = 12–18º
b = 6.4044 (13) ŵ = 0.65 mm1
c = 9.928 (2) ÅT = 293 (2) K
β = 122.18 (3)ºBlock, colourless
V = 756.2 (4) Å30.12 × 0.09 × 0.06 mm
Z = 4

Data collection

Rigaku R-AXIS RAPID IP diffractometer859 independent reflections
Radiation source: fine-focus sealed tube742 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.035
T = 293(2) Kθmax = 27.5º
Oscillation scansθmin = 3.4º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)h = −18→18
Tmin = 0.932, Tmax = 0.962k = −8→7
3518 measured reflectionsl = −12→12

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029All H-atom parameters refined
wR(F2) = 0.081  w = 1/[σ2(Fo2) + (0.0491P)2] where P = (Fo2 + 2Fc2)/3
S = 1.09(Δ/σ)max < 0.001
859 reflectionsΔρmax = 0.25 e Å3
63 parametersΔρmin = −0.22 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
S10.08684 (3)0.07452 (6)−0.17828 (4)0.03333 (18)
N10.13246 (12)0.4379 (2)0.15290 (16)0.0330 (3)
N20.11117 (12)0.2436 (2)0.08916 (15)0.0350 (3)
N30.13151 (11)0.4757 (2)−0.06502 (15)0.0315 (3)
C10.11097 (11)0.2743 (2)−0.04273 (16)0.0275 (3)
C20.14361 (13)0.5723 (3)0.06089 (18)0.0331 (4)
H10.1365 (17)0.462 (4)0.244 (3)0.053 (6)*
H20.1600 (16)0.725 (3)0.083 (2)0.042 (5)*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0383 (3)0.0327 (3)0.0299 (3)0.00536 (14)0.0188 (2)−0.00149 (13)
N10.0378 (7)0.0423 (8)0.0238 (7)0.0035 (5)0.0197 (6)−0.0008 (5)
N20.0434 (7)0.0387 (8)0.0284 (7)0.0037 (5)0.0228 (6)0.0035 (5)
N30.0383 (7)0.0365 (7)0.0258 (7)−0.0025 (5)0.0212 (6)−0.0017 (5)
C10.0280 (7)0.0346 (8)0.0215 (7)0.0031 (5)0.0143 (6)0.0022 (5)
C20.0357 (8)0.0387 (9)0.0270 (8)−0.0029 (6)0.0181 (7)−0.0034 (6)

Geometric parameters (Å, °)

S1—C11.7541 (15)N2—C11.3225 (19)
S1—S1i2.0693 (11)N3—C21.322 (2)
N1—C21.324 (2)N3—C11.3653 (19)
N1—N21.3549 (18)C2—H21.004 (19)
N1—H10.89 (2)
C1—S1—S1i101.72 (5)N2—C1—N3114.30 (13)
C2—N1—N2110.63 (13)N2—C1—S1123.30 (12)
C2—N1—H1128.6 (15)N3—C1—S1122.40 (11)
N2—N1—H1120.8 (15)N3—C2—N1110.21 (15)
C1—N2—N1102.11 (13)N3—C2—H2124.4 (12)
C2—N3—C1102.74 (13)N1—C2—H2125.4 (12)

Symmetry codes: (i) −x, y, −z−1/2.

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···N3ii0.89 (2)1.97 (2)2.8617 (19)174.9 (19)

Symmetry codes: (ii) x, −y+1, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RZ2177).

References

  • De Luca, L. (2006). Curr. Med. Chem 13, 1–23. [PubMed]
  • Di Santo, R., Tafi, A., Costi, R., Botta, M., Artico, M., Corelli, F., Forte, M., Caporuscio, F., Angiolella, L. & Palamara, A. T. (2005). J. Med. Chem.48, 5140–5153. [PubMed]
  • Fringuelli, R., Milanese, L. & Schiaffella, F. (2005). Mini-Rev. Med. Chem.5, 1061–1073. [PubMed]
  • Higashi, T. (1995). ABSCOR Rigaku Corporation, Tokyo, Japan.
  • Menozzi, G., Merello, L., Fossa, P., Schenone, S., Ranise, A., Mosti, L., Bondavalli, F., Loddo, R., Murgioni, C., Mascia, V., La Colla, P. & Tamburini, E. (2004). Bioorg. Med. Chem.12, 5465–5483. [PubMed]
  • Rigaku (1998). RAPID-AUTO Rigaku Corporation, Tokyo, Japan.
  • Sheldrick, G. M. (1993). SHELXTL/PC Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1997). SHELXL97 and SHELXS97 University of Göttingen, Germany.

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