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

Gervasio, G.; Marabello, D.; Bertolotti, F.

doi:10.1107/S1600536810043060

organic compounds

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ISSN: 2056-9890

Volume 66| Part 12| December 2010| Page o3120

https://doi.org/10.1107/S1600536810043060

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

Giuliana Gervasio,^a ^* Domenica Marabello ^a and Federica Bertolotti ^a

^aDipartimento di Chimica I, F.M. e Centro CrisDi, University of Turin, Via P. Giuria 7, 10125, Torino, Italy
^*Correspondence e-mail: giuliana.gervasio@unito.it

(Received 15 October 2010; accepted 22 October 2010; online 10 November 2010)

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 ); Tosco et al. (2004 ). For a related structure, see: Dutov et al.(2007 ).

Experimental

Crystal data

C₁₄H₁₀N₂O₄S₂
M_r = 334.36
Orthorhombic, P n a 2₁
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 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.836, T_max = 1.000
7933 measured reflections
2255 independent reflections
2134 reflections with I > 2σ(I)
R_int = 0.023
θ_max = 62.2°

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.084
S = 1.05
2255 reflections
199 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.13 e Å⁻³
Absolute structure: Flack (1983 ), 1039 Friedel pairs
Flack parameter: 0.010 (17)

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

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810043060/cv2780Isup2.hkl

checkCIF report

Comment top

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).

Related literature top

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); Tosco et al. (2004). For a related structure, see: Dutov et al.(2007).

Experimental top

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

Structure description top

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); Tosco et al. (2004). For a related structure, see: Dutov et al.(2007).

Computing details top

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

Figures top

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

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

Crystal data top

C₁₄H₁₀N₂O₄S₂	D_x = 1.497 Mg m⁻³
M_r = 334.36	Cu Kα radiation, λ = 1.5418 Å
Orthorhombic, Pna2₁	Cell parameters from 5370 reflections
a = 15.0182 (2) Å	θ = 3.8–62.0°
b = 5.5402 (1) Å	µ = 3.44 mm⁻¹
c = 17.8280 (2) Å	T = 293 K
V = 1483.36 (4) Å³	Prismatic, colorless
Z = 4	0.20 × 0.16 × 0.14 mm
F(000) = 688

Data collection top

Gemini R Ultra diffractometer	2255 independent reflections
Radiation source: Ultra (Cu) X-ray Source	2134 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.023
Detector resolution: 10.2890 pixels mm^-1	θ_max = 62.2°, θ_min = 5.0°
f scans	h = −17→16
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	k = −6→5
T_min = 0.836, T_max = 1.000	l = −20→20
7933 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.084	w = 1/[σ²(F_o²) + (0.0626P)² + 0.0158P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2255 reflections	Δρ_max = 0.20 e Å⁻³
199 parameters	Δρ_min = −0.13 e Å⁻³
1 restraint	Absolute structure: Flack (1983), 1039 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.010 (17)

Crystal data top

C₁₄H₁₀N₂O₄S₂	V = 1483.36 (4) Å³
M_r = 334.36	Z = 4
Orthorhombic, Pna2₁	Cu Kα radiation
a = 15.0182 (2) Å	µ = 3.44 mm⁻¹
b = 5.5402 (1) Å	T = 293 K
c = 17.8280 (2) Å	0.20 × 0.16 × 0.14 mm

Data collection top

Gemini R Ultra diffractometer	2255 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	2134 reflections with I > 2σ(I)
T_min = 0.836, T_max = 1.000	R_int = 0.023
7933 measured reflections	θ_max = 62.2°

Refinement top

R[F² > 2σ(F²)] = 0.030	H-atom parameters constrained
wR(F²) = 0.084	Δρ_max = 0.20 e Å⁻³
S = 1.05	Δρ_min = −0.13 e Å⁻³
2255 reflections	Absolute structure: Flack (1983), 1039 Friedel pairs
199 parameters	Absolute structure parameter: 0.010 (17)
1 restraint

Special details top

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) top

	x	y	z	U_iso*/U_eq
C1	0.35417 (17)	0.1230 (4)	0.94838 (14)	0.0566 (5)
C2	0.39856 (16)	0.1654 (4)	1.01631 (14)	0.0538 (5)
C3	0.47584 (18)	0.0455 (5)	0.83468 (14)	0.0581 (6)
C4	0.4633 (2)	0.2458 (5)	0.78924 (16)	0.0724 (7)
H4A	0.4065	0.3080	0.7814	0.087*
C5	0.5353 (3)	0.3495 (7)	0.7563 (2)	0.0918 (11)
H5A	0.5277	0.4827	0.7252	0.110*
C6	0.6182 (3)	0.2605 (8)	0.7684 (2)	0.0959 (11)
H6A	0.6670	0.3351	0.7461	0.115*
C7	0.6311 (2)	0.0621 (9)	0.8129 (2)	0.0975 (12)
H7A	0.6881	0.0014	0.8203	0.117*
C8	0.5582 (2)	−0.0488 (6)	0.84725 (17)	0.0777 (8)
H8A	0.5658	−0.1832	0.8778	0.093*
C9	0.56551 (16)	0.2429 (4)	1.07525 (13)	0.0555 (6)
C10	0.58306 (19)	0.4240 (5)	1.02395 (18)	0.0676 (7)
H10A	0.5503	0.4356	0.9798	0.081*
C11	0.6499 (2)	0.5868 (5)	1.0393 (2)	0.0762 (8)
H11A	0.6613	0.7112	1.0056	0.091*
C12	0.6999 (2)	0.5685 (5)	1.1036 (2)	0.0766 (8)
H12A	0.7448	0.6797	1.1134	0.092*
C13	0.6829 (2)	0.3840 (6)	1.15337 (19)	0.0788 (8)
H13A	0.7175	0.3688	1.1964	0.095*
C14	0.6155 (2)	0.2229 (6)	1.14018 (17)	0.0684 (7)
H14A	0.6035	0.1010	1.1746	0.082*
O1	0.28139 (13)	0.4102 (3)	0.99925 (13)	0.0742 (5)
O2	0.36323 (16)	0.4572 (4)	1.10686 (15)	0.0875 (7)
O3	0.4114 (2)	−0.3036 (4)	0.91510 (14)	0.0920 (7)
O4	0.31016 (18)	−0.0940 (5)	0.82679 (15)	0.1039 (8)
N1	0.28650 (15)	0.2629 (5)	0.93815 (14)	0.0701 (6)
N2	0.35456 (14)	0.3441 (4)	1.04923 (14)	0.0635 (5)
S1	0.48529 (5)	0.01160 (11)	1.05918 (5)	0.0699 (2)
S2	0.38327 (5)	−0.08944 (13)	0.87725 (4)	0.0696 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0491 (13)	0.0607 (12)	0.0600 (14)	−0.0109 (10)	0.0043 (11)	0.0001 (12)
C2	0.0525 (12)	0.0502 (11)	0.0587 (14)	−0.0059 (10)	0.0079 (10)	−0.0043 (10)
C3	0.0677 (16)	0.0610 (14)	0.0456 (13)	−0.0054 (11)	−0.0020 (11)	−0.0079 (10)
C4	0.0842 (18)	0.0719 (16)	0.0610 (15)	0.0049 (14)	0.0063 (14)	0.0019 (14)
C5	0.120 (3)	0.080 (2)	0.0751 (19)	−0.008 (2)	0.030 (2)	0.0072 (16)
C6	0.091 (2)	0.120 (3)	0.076 (2)	−0.030 (2)	0.0235 (18)	−0.008 (2)
C7	0.067 (2)	0.151 (4)	0.075 (2)	0.0048 (19)	0.0035 (16)	−0.001 (2)
C8	0.0695 (19)	0.101 (2)	0.0628 (16)	0.0053 (16)	−0.0018 (13)	0.0043 (15)
C9	0.0526 (13)	0.0510 (11)	0.0631 (15)	0.0039 (9)	0.0033 (11)	0.0003 (10)
C10	0.0629 (16)	0.0666 (14)	0.0731 (17)	0.0052 (12)	−0.0055 (13)	0.0093 (13)
C11	0.0633 (17)	0.0614 (14)	0.104 (2)	0.0004 (13)	0.0009 (17)	0.0146 (15)
C12	0.0595 (16)	0.0703 (16)	0.100 (2)	−0.0051 (13)	0.0000 (16)	−0.0116 (18)
C13	0.0634 (16)	0.104 (2)	0.0688 (17)	−0.0045 (15)	−0.0104 (14)	−0.0098 (16)
C14	0.0734 (17)	0.0754 (17)	0.0564 (14)	0.0003 (14)	−0.0004 (12)	0.0070 (13)
O1	0.0579 (10)	0.0763 (11)	0.0884 (14)	0.0081 (9)	0.0033 (9)	−0.0055 (10)
O2	0.0837 (14)	0.0954 (15)	0.0832 (14)	0.0031 (11)	0.0031 (12)	−0.0354 (13)
O3	0.136 (2)	0.0522 (10)	0.0875 (15)	−0.0183 (11)	0.0244 (13)	−0.0049 (10)
O4	0.0855 (15)	0.139 (2)	0.0869 (17)	−0.0348 (15)	−0.0055 (13)	−0.0339 (14)
N1	0.0576 (12)	0.0834 (14)	0.0693 (13)	−0.0066 (11)	−0.0004 (11)	0.0002 (12)
N2	0.0566 (12)	0.0684 (12)	0.0653 (13)	−0.0045 (10)	0.0050 (10)	−0.0112 (11)
S1	0.0718 (4)	0.0536 (3)	0.0843 (5)	−0.0042 (3)	−0.0134 (4)	0.0067 (3)
S2	0.0740 (4)	0.0725 (4)	0.0624 (4)	−0.0216 (3)	0.0049 (3)	−0.0155 (3)

Geometric parameters (Å, º) top

C1—N1	1.291 (4)	C9—C10	1.383 (4)
C1—C2	1.402 (4)	C9—C14	1.384 (4)
C1—S2	1.784 (3)	C9—S1	1.782 (2)
C2—N2	1.327 (3)	C10—C11	1.377 (4)
C2—S1	1.734 (3)	C10—H10A	0.9300
C3—C8	1.362 (4)	C11—C12	1.374 (5)
C3—C4	1.387 (4)	C11—H11A	0.9300
C3—S2	1.752 (3)	C12—C13	1.378 (5)
C4—C5	1.358 (4)	C12—H12A	0.9300
C4—H4A	0.9300	C13—C14	1.370 (4)
C5—C6	1.357 (6)	C13—H13A	0.9300
C5—H5A	0.9300	C14—H14A	0.9300
C6—C7	1.370 (6)	O1—N1	1.363 (3)
C6—H6A	0.9300	O1—N2	1.461 (3)
C7—C8	1.396 (5)	O2—N2	1.211 (3)
C7—H7A	0.9300	O3—S2	1.429 (3)
C8—H8A	0.9300	O4—S2	1.420 (3)

N1—C1—C2	113.3 (2)	C11—C10—C9	118.9 (3)
N1—C1—S2	119.2 (2)	C11—C10—H10A	120.6
C2—C1—S2	127.4 (2)	C9—C10—H10A	120.6
N2—C2—C1	105.7 (2)	C12—C11—C10	121.1 (3)
N2—C2—S1	123.1 (2)	C12—C11—H11A	119.5
C1—C2—S1	130.9 (2)	C10—C11—H11A	119.5
C8—C3—C4	121.8 (3)	C11—C12—C13	119.4 (3)
C8—C3—S2	119.1 (2)	C11—C12—H12A	120.3
C4—C3—S2	119.1 (2)	C13—C12—H12A	120.3
C5—C4—C3	118.9 (3)	C14—C13—C12	120.6 (3)
C5—C4—H4A	120.6	C14—C13—H13A	119.7
C3—C4—H4A	120.6	C12—C13—H13A	119.7
C6—C5—C4	120.6 (4)	C13—C14—C9	119.5 (3)
C6—C5—H5A	119.7	C13—C14—H14A	120.3
C4—C5—H5A	119.7	C9—C14—H14A	120.3
C5—C6—C7	120.9 (3)	N1—O1—N2	107.14 (18)
C5—C6—H6A	119.6	C1—N1—O1	106.9 (2)
C7—C6—H6A	119.6	O2—N2—C2	135.1 (2)
C6—C7—C8	119.8 (4)	O2—N2—O1	117.9 (2)
C6—C7—H7A	120.1	C2—N2—O1	107.0 (2)
C8—C7—H7A	120.1	C2—S1—C9	103.02 (11)
C3—C8—C7	118.1 (3)	O4—S2—O3	120.89 (17)
C3—C8—H8A	120.9	O4—S2—C3	110.29 (15)
C7—C8—H8A	120.9	O3—S2—C3	108.92 (15)
C10—C9—C14	120.5 (2)	O4—S2—C1	105.81 (14)
C10—C9—S1	123.0 (2)	O3—S2—C1	106.53 (13)
C14—C9—S1	116.3 (2)	C3—S2—C1	102.76 (12)

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₂O₄S₂
M_r	334.36
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	15.0182 (2), 5.5402 (1), 17.8280 (2)
V (Å³)	1483.36 (4)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	3.44
Crystal size (mm)	0.20 × 0.16 × 0.14

Data collection
Diffractometer	Gemini R Ultra
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008)
T_min, T_max	0.836, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7933, 2255, 2134
R_int	0.023
θ_max (°)	62.2
(sin θ/λ)_max (Å⁻¹)	0.574

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.084, 1.05
No. of reflections	2255
No. of parameters	199
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.13
Absolute structure	Flack (1983), 1039 Friedel pairs
Absolute structure parameter	0.010 (17)

Computer programs: CrysAlis CCD (Oxford Diffraction, 2008), CrysAlis RED (Oxford Diffraction, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Acknowledgements

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

References

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