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Acta Crystallogr Sect E Struct Rep Online. 2010 December 1; 66(Pt 12): o3120.
Published online 2010 November 10. doi:  10.1107/S1600536810043060
PMCID: PMC3011692

3-Phenyl­sulfanyl-4-phenyl­sulfonyl-1,2,5-oxadiazole 2-oxide

Abstract

In the title compound, C14H10N2O4S2,the furoxan heterocyclic ring and the two S atoms are almost co-planar, with a mean deviation of 0.036 Å. The bond lengths in the penta­gonal ring show electron delocalization and the furoxan N—O bond length is quite short [1.211 (3) Å]. The dihedral angles between the central ring and pendant phenyl rings are 78.05 (14) and 84.28 (2)°.

Related literature

This is part of a study on phenyl­sulfonyl-substituted furoxans as inter­mediates for the synthesis of new functionalized furoxans with potential biological properties as N,O-donors. For details of the synthesis, see: Sorba et al. (1996 [triangle]); Tosco et al. (2004 [triangle]). For a related structure, see: Dutov et al.(2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o3120-scheme1.jpg

Experimental

Crystal data

  • C14H10N2O4S2
  • M r = 334.36
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3120-efi1.jpg
  • a = 15.0182 (2) Å
  • b = 5.5402 (1) Å
  • c = 17.8280 (2) Å
  • V = 1483.36 (4) Å3
  • Z = 4
  • Cu Kα radiation
  • μ = 3.44 mm−1
  • T = 293 K
  • 0.20 × 0.16 × 0.14 mm

Data collection

  • Gemini R Ultra diffractometer
  • Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008 [triangle]) T min = 0.836, T max = 1.000
  • 7933 measured reflections
  • 2255 independent reflections
  • 2134 reflections with I > 2σ(I)
  • R int = 0.023
  • θmax = 62.2°

Refinement

  • R[F 2 > 2σ(F 2)] = 0.030
  • wR(F 2) = 0.084
  • S = 1.05
  • 2255 reflections
  • 199 parameters
  • 1 restraint
  • H-atom parameters constrained
  • Δρmax = 0.20 e Å−3
  • Δρmin = −0.13 e Å−3
  • Absolute structure: Flack (1983 [triangle]), 1039 Friedel pairs
  • Flack parameter: 0.010 (17)

Data collection: CrysAlis CCD (Oxford Diffraction, 2008 [triangle]); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 [triangle]); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: XP in SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810043060/cv2780sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043060/cv2780Isup2.hkl

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

Acknowledgments

We thank Professor A. Gasco for supplying crystals of the title compound.

supplementary crystallographic information

Comment

The title compound shows a planar moiety including the two sulfur atoms and the furoxanic ring, with a mean deviation from planarity of 0.036 Å. The planar ring contains also a significant delocalization in the N2C2C1N1O1 fragment, while the O1—N2 bond is quite greater than the corresponding N1—O1 (1.461 (3) Å vs. 1.363 (3) Å). The N2—O2 bond length is quite short (1.211 (3) Å), similar however to that reported by Sorba et al. (1996) and Dutov et al. (2007).

Experimental

The 3-phenylthio-4-phenylsulfonyl-furoxanhas been obtained according to Tosco et al. (2004).

Refinement

C-bound H atoms have been placed in geometrically idealized positions (C—H = 0.93 Å), and refined as riding, with Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound showing the atomic numbering and 30% probability displacements ellipsoids.

Crystal data

C14H10N2O4S2Dx = 1.497 Mg m3
Mr = 334.36Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, Pna21Cell parameters from 5370 reflections
a = 15.0182 (2) Åθ = 3.8–62.0°
b = 5.5402 (1) ŵ = 3.44 mm1
c = 17.8280 (2) ÅT = 293 K
V = 1483.36 (4) Å3Prismatic, colorless
Z = 40.20 × 0.16 × 0.14 mm
F(000) = 688

Data collection

Gemini R Ultra diffractometer2255 independent reflections
Radiation source: Ultra (Cu) X-ray Source2134 reflections with I > 2σ(I)
mirrorRint = 0.023
Detector resolution: 10.2890 pixels mm-1θmax = 62.2°, θmin = 5.0°
f scansh = −17→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)k = −6→5
Tmin = 0.836, Tmax = 1.000l = −20→20
7933 measured reflections

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.030H-atom parameters constrained
wR(F2) = 0.084w = 1/[σ2(Fo2) + (0.0626P)2 + 0.0158P] where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
2255 reflectionsΔρmax = 0.20 e Å3
199 parametersΔρmin = −0.13 e Å3
1 restraintAbsolute structure: Flack (1983), 1039 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.010 (17)

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
C10.35417 (17)0.1230 (4)0.94838 (14)0.0566 (5)
C20.39856 (16)0.1654 (4)1.01631 (14)0.0538 (5)
C30.47584 (18)0.0455 (5)0.83468 (14)0.0581 (6)
C40.4633 (2)0.2458 (5)0.78924 (16)0.0724 (7)
H4A0.40650.30800.78140.087*
C50.5353 (3)0.3495 (7)0.7563 (2)0.0918 (11)
H5A0.52770.48270.72520.110*
C60.6182 (3)0.2605 (8)0.7684 (2)0.0959 (11)
H6A0.66700.33510.74610.115*
C70.6311 (2)0.0621 (9)0.8129 (2)0.0975 (12)
H7A0.68810.00140.82030.117*
C80.5582 (2)−0.0488 (6)0.84725 (17)0.0777 (8)
H8A0.5658−0.18320.87780.093*
C90.56551 (16)0.2429 (4)1.07525 (13)0.0555 (6)
C100.58306 (19)0.4240 (5)1.02395 (18)0.0676 (7)
H10A0.55030.43560.97980.081*
C110.6499 (2)0.5868 (5)1.0393 (2)0.0762 (8)
H11A0.66130.71121.00560.091*
C120.6999 (2)0.5685 (5)1.1036 (2)0.0766 (8)
H12A0.74480.67971.11340.092*
C130.6829 (2)0.3840 (6)1.15337 (19)0.0788 (8)
H13A0.71750.36881.19640.095*
C140.6155 (2)0.2229 (6)1.14018 (17)0.0684 (7)
H14A0.60350.10101.17460.082*
O10.28139 (13)0.4102 (3)0.99925 (13)0.0742 (5)
O20.36323 (16)0.4572 (4)1.10686 (15)0.0875 (7)
O30.4114 (2)−0.3036 (4)0.91510 (14)0.0920 (7)
O40.31016 (18)−0.0940 (5)0.82679 (15)0.1039 (8)
N10.28650 (15)0.2629 (5)0.93815 (14)0.0701 (6)
N20.35456 (14)0.3441 (4)1.04923 (14)0.0635 (5)
S10.48529 (5)0.01160 (11)1.05918 (5)0.0699 (2)
S20.38327 (5)−0.08944 (13)0.87725 (4)0.0696 (2)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0491 (13)0.0607 (12)0.0600 (14)−0.0109 (10)0.0043 (11)0.0001 (12)
C20.0525 (12)0.0502 (11)0.0587 (14)−0.0059 (10)0.0079 (10)−0.0043 (10)
C30.0677 (16)0.0610 (14)0.0456 (13)−0.0054 (11)−0.0020 (11)−0.0079 (10)
C40.0842 (18)0.0719 (16)0.0610 (15)0.0049 (14)0.0063 (14)0.0019 (14)
C50.120 (3)0.080 (2)0.0751 (19)−0.008 (2)0.030 (2)0.0072 (16)
C60.091 (2)0.120 (3)0.076 (2)−0.030 (2)0.0235 (18)−0.008 (2)
C70.067 (2)0.151 (4)0.075 (2)0.0048 (19)0.0035 (16)−0.001 (2)
C80.0695 (19)0.101 (2)0.0628 (16)0.0053 (16)−0.0018 (13)0.0043 (15)
C90.0526 (13)0.0510 (11)0.0631 (15)0.0039 (9)0.0033 (11)0.0003 (10)
C100.0629 (16)0.0666 (14)0.0731 (17)0.0052 (12)−0.0055 (13)0.0093 (13)
C110.0633 (17)0.0614 (14)0.104 (2)0.0004 (13)0.0009 (17)0.0146 (15)
C120.0595 (16)0.0703 (16)0.100 (2)−0.0051 (13)0.0000 (16)−0.0116 (18)
C130.0634 (16)0.104 (2)0.0688 (17)−0.0045 (15)−0.0104 (14)−0.0098 (16)
C140.0734 (17)0.0754 (17)0.0564 (14)0.0003 (14)−0.0004 (12)0.0070 (13)
O10.0579 (10)0.0763 (11)0.0884 (14)0.0081 (9)0.0033 (9)−0.0055 (10)
O20.0837 (14)0.0954 (15)0.0832 (14)0.0031 (11)0.0031 (12)−0.0354 (13)
O30.136 (2)0.0522 (10)0.0875 (15)−0.0183 (11)0.0244 (13)−0.0049 (10)
O40.0855 (15)0.139 (2)0.0869 (17)−0.0348 (15)−0.0055 (13)−0.0339 (14)
N10.0576 (12)0.0834 (14)0.0693 (13)−0.0066 (11)−0.0004 (11)0.0002 (12)
N20.0566 (12)0.0684 (12)0.0653 (13)−0.0045 (10)0.0050 (10)−0.0112 (11)
S10.0718 (4)0.0536 (3)0.0843 (5)−0.0042 (3)−0.0134 (4)0.0067 (3)
S20.0740 (4)0.0725 (4)0.0624 (4)−0.0216 (3)0.0049 (3)−0.0155 (3)

Geometric parameters (Å, °)

C1—N11.291 (4)C9—C101.383 (4)
C1—C21.402 (4)C9—C141.384 (4)
C1—S21.784 (3)C9—S11.782 (2)
C2—N21.327 (3)C10—C111.377 (4)
C2—S11.734 (3)C10—H10A0.9300
C3—C81.362 (4)C11—C121.374 (5)
C3—C41.387 (4)C11—H11A0.9300
C3—S21.752 (3)C12—C131.378 (5)
C4—C51.358 (4)C12—H12A0.9300
C4—H4A0.9300C13—C141.370 (4)
C5—C61.357 (6)C13—H13A0.9300
C5—H5A0.9300C14—H14A0.9300
C6—C71.370 (6)O1—N11.363 (3)
C6—H6A0.9300O1—N21.461 (3)
C7—C81.396 (5)O2—N21.211 (3)
C7—H7A0.9300O3—S21.429 (3)
C8—H8A0.9300O4—S21.420 (3)
N1—C1—C2113.3 (2)C11—C10—C9118.9 (3)
N1—C1—S2119.2 (2)C11—C10—H10A120.6
C2—C1—S2127.4 (2)C9—C10—H10A120.6
N2—C2—C1105.7 (2)C12—C11—C10121.1 (3)
N2—C2—S1123.1 (2)C12—C11—H11A119.5
C1—C2—S1130.9 (2)C10—C11—H11A119.5
C8—C3—C4121.8 (3)C11—C12—C13119.4 (3)
C8—C3—S2119.1 (2)C11—C12—H12A120.3
C4—C3—S2119.1 (2)C13—C12—H12A120.3
C5—C4—C3118.9 (3)C14—C13—C12120.6 (3)
C5—C4—H4A120.6C14—C13—H13A119.7
C3—C4—H4A120.6C12—C13—H13A119.7
C6—C5—C4120.6 (4)C13—C14—C9119.5 (3)
C6—C5—H5A119.7C13—C14—H14A120.3
C4—C5—H5A119.7C9—C14—H14A120.3
C5—C6—C7120.9 (3)N1—O1—N2107.14 (18)
C5—C6—H6A119.6C1—N1—O1106.9 (2)
C7—C6—H6A119.6O2—N2—C2135.1 (2)
C6—C7—C8119.8 (4)O2—N2—O1117.9 (2)
C6—C7—H7A120.1C2—N2—O1107.0 (2)
C8—C7—H7A120.1C2—S1—C9103.02 (11)
C3—C8—C7118.1 (3)O4—S2—O3120.89 (17)
C3—C8—H8A120.9O4—S2—C3110.29 (15)
C7—C8—H8A120.9O3—S2—C3108.92 (15)
C10—C9—C14120.5 (2)O4—S2—C1105.81 (14)
C10—C9—S1123.0 (2)O3—S2—C1106.53 (13)
C14—C9—S1116.3 (2)C3—S2—C1102.76 (12)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2780).

References

  • Dutov, M. D., Serushkina, O. V., Shevelev, S. A. & Lyssenko, K. A. (2007). Mendeleev Commun.17, 347–348.
  • Flack, H. D. (1983). Acta Cryst. A39, 876–881.
  • Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED Oxford Diffraction Ltd, Yarnton, England.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sorba, G., Ermondi, G., Fruttero, R., Galli, U. & Gasco, A. (1996). J. Heterocycl. Chem.33, 327–334.
  • Tosco, P., Bertinaria, M., Di Stilo, A., Marini, E., Rolando, B., Sorba, G., Fruttero, R. & Gasco, A. (2004). Farmaco, 59, 359–371. [PubMed]

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