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Acta Crystallogr Sect E Struct Rep Online. 2008 November 1; 64(Pt 11): o2182.
Published online 2008 October 25. doi:  10.1107/S1600536808034314
PMCID: PMC2959731

1,2-Bis(p-tolyl­sulfon­yl)hydrazine

Abstract

In the title compound, C14H16N2O4S2, the dihedral angle between the aromatic ring planes is 76.8 (3)° and the S—N—N—S torsion angle is 122.5 (3)°. In the crystal structure, mol­ecules form a chain structure by way of N—H(...)O hydrogen bonds.

Related literature

For background on aroylhydrazines, see: Bu et al. (2001 [triangle]); Ranford et al. (1998 [triangle]), Agarwal & Sharma (1993 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-64-o2182-scheme1.jpg

Experimental

Crystal data

  • C14H16N2O4S2
  • M r = 340.41
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o2182-efi1.jpg
  • a = 15.7318 (16) Å
  • b = 10.7016 (12) Å
  • c = 9.4943 (9) Å
  • β = 90.102 (2)°
  • V = 1598.4 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.35 mm−1
  • T = 298 (2) K
  • 0.33 × 0.11 × 0.04 mm

Data collection

  • Bruker SMART CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2000 [triangle]) T min = 0.893, T max = 0.986
  • 7984 measured reflections
  • 2808 independent reflections
  • 1132 reflections with I > 2σ(I)
  • R int = 0.108

Refinement

  • R[F 2 > 2σ(F 2)] = 0.065
  • wR(F 2) = 0.080
  • S = 0.97
  • 2808 reflections
  • 199 parameters
  • H-atom parameters constrained
  • Δρmax = 0.23 e Å−3
  • Δρmin = −0.27 e Å−3

Data collection: SMART (Bruker, 2000 [triangle]); cell refinement: SAINT (Bruker, 2000 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808034314/hb2824sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808034314/hb2824Isup2.hkl

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

Acknowledgments

The authors thank the National Natural Science Foundation of China (20671073), Shandong Province Scientific and Technological Brainstorm Project (2008 GG10002022), the National Natural Science Foundation of Shandong (Y2007B60) and the Science and Technology Foundation of Weifang for research grants.

supplementary crystallographic information

Comment

Aroylhydrazines have drawn much attention in recent years due to their wide biological and pharmacological activities, such as antitumor (Ranford et al., 1998), antidiabetic (Bu et al., 2001) antitubercular (Agarwal & Sharma, 1993) activities. As part of our studies in this area, we now report the synthesis and crystal structure of the title compound, (I).

In (I), the dihedral angle between the two phenyl rings of (C1—C6 and C8—C13) is 76.8 (3)°. The S=O bond distances are characteristic of double bonds. The N1—N2 single bond of 1.407 (4) is in agreement with that of other acylhydrazone compounds in which the acylhydrazone takes a ketonic form.

In the crystal, N—H···O hydrogen bonds (Table 1) help to establish the packing.

Experimental

5 mmol of 4-toluene sulfonyl chloride (5 mmol) was added to a solution of hydrazine (2.5 mmol) in 10 ml of ethanol at room temperature. The mixture was continuously stirred for 2 h at temperature, the solid product was collected by filtration and dried in vacuo (yield 58%). Clear blocks of (I) were obtained by evaporation from a methanol/water solution after 10 days.

Figures

Fig. 1.
The molecular structure of (I) showing 30% displacement ellipsoids (arbitrary spheres for the H atoms).

Crystal data

C14H16N2O4S2F(000) = 712
Mr = 340.41Dx = 1.415 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 586 reflections
a = 15.7318 (16) Åθ = 2.3–25.0°
b = 10.7016 (12) ŵ = 0.35 mm1
c = 9.4943 (9) ÅT = 298 K
β = 90.102 (2)°Flake, colourless
V = 1598.4 (3) Å30.33 × 0.11 × 0.04 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer2808 independent reflections
Radiation source: fine-focus sealed tube1132 reflections with I > 2σ(I)
graphiteRint = 0.108
ω scansθmax = 25.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000)h = −18→12
Tmin = 0.893, Tmax = 0.986k = −12→12
7984 measured reflectionsl = −11→11

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)] = 0.065Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080H-atom parameters constrained
S = 0.97w = 1/[σ2(Fo2) + (0.0003P)2] where P = (Fo2 + 2Fc2)/3
2808 reflections(Δ/σ)max < 0.001
199 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = −0.27 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
S10.82111 (9)0.60680 (14)−0.00482 (14)0.0542 (4)
S20.70156 (9)0.91574 (15)−0.01299 (15)0.0588 (4)
N10.7517 (2)0.7008 (4)0.0725 (4)0.0513 (12)
H10.74840.67940.16400.062*
N20.7743 (2)0.8278 (4)0.0630 (4)0.0535 (12)
H2A0.78230.85710.15080.064*
O10.82411 (18)0.6447 (3)−0.1491 (3)0.0628 (10)
O20.7938 (2)0.4847 (3)0.0334 (4)0.0682 (11)
O30.6846 (2)0.8623 (3)−0.1482 (3)0.0701 (11)
O40.7356 (2)1.0395 (3)−0.0015 (4)0.0771 (13)
C10.9213 (3)0.6382 (5)0.0667 (5)0.0446 (14)
C20.9673 (4)0.7381 (5)0.0188 (6)0.0602 (17)
H20.94580.7892−0.05200.072*
C31.0465 (4)0.7620 (5)0.0775 (6)0.0634 (17)
H31.07720.83100.04670.076*
C41.0807 (3)0.6865 (5)0.1799 (6)0.0534 (16)
C51.0339 (4)0.5857 (5)0.2236 (5)0.0579 (15)
H51.05670.53270.29150.069*
C60.9547 (3)0.5604 (5)0.1703 (6)0.0538 (15)
H60.92380.49230.20300.065*
C71.1679 (3)0.7141 (5)0.2376 (6)0.080 (2)
H7A1.18620.64610.29620.121*
H7B1.16610.78950.29240.121*
H7C1.20710.72450.16110.121*
C80.6086 (3)0.9042 (5)0.0880 (5)0.0472 (14)
C90.6008 (4)0.9722 (5)0.2078 (6)0.087 (2)
H90.64481.02400.23740.104*
C100.5265 (4)0.9636 (6)0.2860 (6)0.095 (2)
H100.52141.01150.36730.115*
C110.4622 (4)0.8893 (6)0.2488 (6)0.0659 (18)
C120.4712 (4)0.8228 (5)0.1302 (7)0.087 (2)
H120.42740.76980.10250.104*
C130.5441 (4)0.8306 (5)0.0467 (6)0.083 (2)
H130.54800.7851−0.03650.100*
C140.3808 (3)0.8797 (5)0.3358 (6)0.091 (2)
H14A0.38520.93270.41700.136*
H14B0.37270.79470.36540.136*
H14C0.33320.90550.27940.136*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0498 (10)0.0731 (11)0.0398 (9)0.0048 (9)0.0043 (7)−0.0049 (8)
S20.0622 (11)0.0726 (11)0.0417 (10)0.0093 (10)0.0038 (8)0.0035 (9)
N10.052 (3)0.068 (3)0.034 (3)0.010 (3)0.004 (2)0.002 (2)
N20.054 (3)0.068 (3)0.038 (3)0.010 (3)−0.001 (2)−0.003 (3)
O10.058 (2)0.099 (3)0.031 (2)0.011 (2)0.0041 (17)−0.007 (2)
O20.066 (3)0.056 (2)0.083 (3)−0.009 (2)0.003 (2)−0.001 (2)
O30.073 (3)0.104 (3)0.033 (2)0.021 (2)0.0053 (19)−0.004 (2)
O40.087 (3)0.062 (2)0.082 (3)−0.014 (2)0.012 (2)0.010 (2)
C10.038 (3)0.051 (4)0.045 (4)0.006 (3)0.006 (3)−0.005 (3)
C20.048 (4)0.071 (4)0.061 (4)0.005 (4)0.004 (3)0.022 (3)
C30.048 (4)0.076 (5)0.066 (5)−0.007 (4)0.011 (3)0.008 (4)
C40.051 (4)0.058 (4)0.051 (4)0.007 (4)−0.003 (3)−0.013 (3)
C50.067 (4)0.058 (4)0.049 (4)0.014 (4)−0.012 (3)0.002 (3)
C60.058 (4)0.056 (4)0.047 (4)0.004 (3)0.009 (3)−0.001 (3)
C70.052 (4)0.096 (5)0.093 (6)0.005 (4)−0.012 (4)−0.017 (4)
C80.049 (4)0.055 (4)0.038 (3)0.006 (3)−0.002 (3)−0.003 (3)
C90.081 (5)0.112 (5)0.067 (5)−0.030 (4)0.015 (4)−0.043 (4)
C100.094 (6)0.124 (6)0.069 (5)−0.008 (5)0.034 (4)−0.042 (4)
C110.057 (4)0.082 (5)0.058 (4)0.020 (4)0.005 (4)0.010 (4)
C120.057 (5)0.112 (5)0.092 (6)−0.024 (4)0.007 (4)−0.029 (5)
C130.071 (5)0.103 (5)0.075 (5)−0.003 (4)0.001 (4)−0.031 (4)
C140.068 (4)0.132 (5)0.072 (5)0.026 (4)0.017 (3)0.020 (4)

Geometric parameters (Å, °)

S1—O21.423 (3)C5—H50.9300
S1—O11.429 (3)C6—H60.9300
S1—N11.657 (3)C7—H7A0.9600
S1—C11.748 (5)C7—H7B0.9600
S2—O31.430 (3)C7—H7C0.9600
S2—O41.433 (3)C8—C131.343 (6)
S2—N21.648 (4)C8—C91.356 (6)
S2—C81.754 (4)C9—C101.389 (6)
N1—N21.407 (4)C9—H90.9300
N1—H10.9001C10—C111.333 (7)
N2—H2A0.8998C10—H100.9300
C1—C21.369 (6)C11—C121.340 (7)
C1—C61.391 (6)C11—C141.529 (6)
C2—C31.387 (7)C12—C131.398 (6)
C2—H20.9300C12—H120.9300
C3—C41.373 (7)C13—H130.9300
C3—H30.9300C14—H14A0.9600
C4—C51.370 (6)C14—H14B0.9600
C4—C71.507 (6)C14—H14C0.9600
C5—C61.371 (6)
O2—S1—O1121.0 (2)C5—C6—C1119.0 (5)
O2—S1—N1104.1 (2)C5—C6—H6120.5
O1—S1—N1106.0 (2)C1—C6—H6120.5
O2—S1—C1110.5 (3)C4—C7—H7A109.5
O1—S1—C1106.6 (2)C4—C7—H7B109.5
N1—S1—C1107.8 (2)H7A—C7—H7B109.5
O3—S2—O4120.5 (2)C4—C7—H7C109.5
O3—S2—N2107.0 (2)H7A—C7—H7C109.5
O4—S2—N2103.6 (2)H7B—C7—H7C109.5
O3—S2—C8107.9 (2)C13—C8—C9119.3 (5)
O4—S2—C8109.6 (2)C13—C8—S2120.8 (4)
N2—S2—C8107.4 (2)C9—C8—S2119.8 (5)
N2—N1—S1113.0 (3)C8—C9—C10119.4 (6)
N2—N1—H1108.8C8—C9—H9120.3
S1—N1—H1108.2C10—C9—H9120.3
N1—N2—S2113.8 (3)C11—C10—C9122.5 (6)
N1—N2—H2A108.2C11—C10—H10118.8
S2—N2—H2A107.5C9—C10—H10118.8
C2—C1—C6120.2 (5)C10—C11—C12117.3 (6)
C2—C1—S1119.9 (5)C10—C11—C14122.2 (6)
C6—C1—S1119.9 (4)C12—C11—C14120.5 (7)
C1—C2—C3119.1 (5)C11—C12—C13122.2 (6)
C1—C2—H2120.5C11—C12—H12118.9
C3—C2—H2120.5C13—C12—H12118.9
C4—C3—C2121.7 (5)C8—C13—C12119.3 (6)
C4—C3—H3119.1C8—C13—H13120.3
C2—C3—H3119.1C12—C13—H13120.3
C5—C4—C3117.9 (6)C11—C14—H14A109.5
C5—C4—C7122.2 (6)C11—C14—H14B109.5
C3—C4—C7119.8 (6)H14A—C14—H14B109.5
C4—C5—C6122.1 (5)C11—C14—H14C109.5
C4—C5—H5119.0H14A—C14—H14C109.5
C6—C5—H5119.0H14B—C14—H14C109.5
O2—S1—N1—N2172.0 (3)C4—C5—C6—C11.3 (8)
O1—S1—N1—N2−59.3 (4)C2—C1—C6—C50.2 (7)
C1—S1—N1—N254.6 (4)S1—C1—C6—C5179.1 (4)
S1—N1—N2—S2122.5 (3)O3—S2—C8—C1313.6 (5)
O3—S2—N2—N1−55.6 (3)O4—S2—C8—C13146.6 (4)
O4—S2—N2—N1176.0 (3)N2—S2—C8—C13−101.5 (5)
C8—S2—N2—N160.1 (4)O3—S2—C8—C9−165.1 (4)
O2—S1—C1—C2165.9 (4)O4—S2—C8—C9−32.1 (5)
O1—S1—C1—C232.5 (4)N2—S2—C8—C979.8 (5)
N1—S1—C1—C2−80.9 (4)C13—C8—C9—C100.4 (9)
O2—S1—C1—C6−13.1 (4)S2—C8—C9—C10179.1 (5)
O1—S1—C1—C6−146.4 (4)C8—C9—C10—C111.0 (10)
N1—S1—C1—C6100.2 (4)C9—C10—C11—C12−0.9 (10)
C6—C1—C2—C3−1.5 (8)C9—C10—C11—C14179.6 (6)
S1—C1—C2—C3179.6 (4)C10—C11—C12—C13−0.5 (10)
C1—C2—C3—C41.5 (9)C14—C11—C12—C13179.0 (5)
C2—C3—C4—C5−0.2 (8)C9—C8—C13—C12−1.7 (8)
C2—C3—C4—C7178.3 (5)S2—C8—C13—C12179.5 (4)
C3—C4—C5—C6−1.2 (8)C11—C12—C13—C81.9 (9)
C7—C4—C5—C6−179.7 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O3i0.902.102.935 (5)155
N2—H2A···O1i0.902.012.857 (5)157

Symmetry codes: (i) x, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB2824).

References

  • Agarwal, R. K. & Sharma, S. (1993). Pol. J. Chem.67, 581–586.
  • Bruker (2000). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Bu, X. H., Gao, Y. X., Chen, W. & Zhang, R. H. (2001). J. Rare Earth, 19, 70–75.
  • Ranford, J. D., Vittal, J. J. & Wang, Y. M. (1998). Inorg. Chem.37, 1226–1231. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]

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