organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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5,5′-Di­phenyl-2,2′-[butane-1,4-diylbis(sulfanedi­yl)]bis­­(1,3,4-oxa­diazole)

aSchool of Perfume and Aroma Technology, Shanghai Institute of Technology, Shanghai 200235, People's Republic of China, bSchool of Chemical Engineering, University of Science and Technology LiaoNing, Anshan 114051, People's Republic of China, and cLiaoyang Supervision and Examination Station of Product Quality, Liaoning Liaoyang 111000, People's Republic of China
*Correspondence e-mail: zhao_submit@yahoo.com.cn

(Received 3 October 2010; accepted 19 October 2010; online 23 October 2010)

The complete mol­ecule of the title compound, C20H18N4O2S2, is generated by crystallographic inversion symmetry. The benzene ring is almost coplanar with the oxadiazole ring [dihedral angle = 7.2 (2)°].

Related literature

Functionalized 1,3,4-oxadiazole derivatives are of inter­est because of their biological activity and their wide applications in medicine, coordination chemistry and their use as organic electroluminescent (EL) devices, since these compounds possess good electron-accepting properties, see: Bentiss et al. (2000[Bentiss, F., Traisnel, M. & Lagrenee, M. (2000). Corros. Sci. 42, 127-146.]); Hughes & Bryce (2005[Hughes, G. & Bryce, M. R. (2005). J. Mater. Chem. 15, 94-107.]); Navidpour et al. (2006[Navidpour, L., Shafaroodi, H., Abdi, K., Amini, M., Ghahremani, M. H., Dehpour, A. R. & Shafiee, A. (2006). Bioorg. Med. Chem. 14, 2507-2517.]).

[Scheme 1]

Experimental

Crystal data
  • C20H18N4O2S2

  • Mr = 410.50

  • Monoclinic, P 21 /c

  • a = 12.202 (2) Å

  • b = 5.9317 (12) Å

  • c = 13.518 (3) Å

  • β = 104.04 (3)°

  • V = 949.2 (3) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 113 K

  • 0.20 × 0.18 × 0.12 mm

Data collection
  • Rigaku Saturn CCD area-detector diffractometer

  • Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]) Tmin = 0.942, Tmax = 0.964

  • 7030 measured reflections

  • 1661 independent reflections

  • 1323 reflections with I > 2σ(I)

  • Rint = 0.053

Refinement
  • R[F2 > 2σ(F2)] = 0.040

  • wR(F2) = 0.128

  • S = 1.10

  • 1661 reflections

  • 128 parameters

  • H-atom parameters constrained

  • Δρmax = 0.28 e Å−3

  • Δρmin = −0.33 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005[Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.]); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Functionalized 1,3,4-oxadiazole derivatives are of interest because of their biological activity and their wide applications in medicine, coordination chemistry and their use as organic electroluminescent (EL) devices, since these compounds possess good electron-accepting properties (Bentiss et al., 2000; Navidpour et al., 2006; Hughes & Bryce, 2005). We report here the synthesis and crystal structure of the title compound, C20H18N4O2S2 (I). In the structure of the title compound the molecule has an inversion centre at the mid-point of the central C10—C10i bond (symmetry code for (i): -x + 1,-y + 3, -z + 1), the asymmetric unit containing half a molecule (Fig. 1). The mean plane of the oxadiazole ring is almost coplanar with the mean plane of the attached benzene ring [dihedral angle 7.2 (2)°]. As a result of π-π conjugation, the Csp2-S bond [S1—C8 = 1.729 (2) Å] is significantly shorter than the Csp3-S bond [S1—C9 = 1.818 (2) Å].

Related literature top

Functionalized 1,3,4-oxadiazole derivatives are of interest because of their biological activity and their wide applications in medicine, coordination chemistry and their use as organic electroluminescent (EL) devices, since these compounds possess good electron-accepting properties, see: Bentiss et al. (2000); Hughes & Bryce (2005); Navidpour et al. (2006).

Experimental top

A suspension of 5-phenyl-1,3,4-oxadiazole-2-thiol (2.0 mmol) and 1,4-dibromobutane (1.0 mmol) in ethanol (10 ml) was stirred at room temperature. The reaction progress was monitored via TLC. The resulting precipitate was filtered off, washed with cold ethanol, dried and purified to give the title compound as a light yellow solid in 93% yield. Crystals of (I) suitable for single-crystal X-ray analysis were grown by slow evaporation of a solution in chloroform-ethanol (1:1).

Refinement top

All H atoms were positioned geometrically (C—H = 0.95–0.99 Å) and allowed to ride on their parent atoms, with Uiso(H) = 1.2Ueq(C).

Computing details top

Data collection: CrystalClear (Rigaku/MSC, 2005); cell refinement: CrystalClear (Rigaku/MSC, 2005); data reduction: CrystalClear (Rigaku/MSC, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I) showing the atom-labelling scheme. Atoms of the inversion-related atoms are indicated by symmetry code 'A' (-x + 1,-y + 3, -z + 1). Displacement ellipsoids are drawn at the 35% probability level.
5,5'-diphenyl-2,2'-[butane-1,4-diylbis(sulfanediyl)]bis(1,3,4-oxadiazole) top
Crystal data top
C20H18N4O2S2F(000) = 428
Mr = 410.50Dx = 1.436 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3017 reflections
a = 12.202 (2) Åθ = 1.7–27.9°
b = 5.9317 (12) ŵ = 0.31 mm1
c = 13.518 (3) ÅT = 113 K
β = 104.04 (3)°Prism, colorless
V = 949.2 (3) Å30.20 × 0.18 × 0.12 mm
Z = 2
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
1661 independent reflections
Radiation source: rotating anode1323 reflections with I > 2σ(I)
Confocal monochromatorRint = 0.053
Detector resolution: 7.31 pixels mm-1θmax = 25.0°, θmin = 1.7°
ϕ and ω scansh = 1214
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
k = 76
Tmin = 0.942, Tmax = 0.964l = 1616
7030 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.128 w = 1/[σ2(Fo2) + (0.0778P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max < 0.001
1661 reflectionsΔρmax = 0.28 e Å3
128 parametersΔρmin = 0.33 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.067 (10)
Crystal data top
C20H18N4O2S2V = 949.2 (3) Å3
Mr = 410.50Z = 2
Monoclinic, P21/cMo Kα radiation
a = 12.202 (2) ŵ = 0.31 mm1
b = 5.9317 (12) ÅT = 113 K
c = 13.518 (3) Å0.20 × 0.18 × 0.12 mm
β = 104.04 (3)°
Data collection top
Rigaku Saturn CCD area-detector
diffractometer
1661 independent reflections
Absorption correction: multi-scan
(CrystalClear; Rigaku/MSC, 2005)
1323 reflections with I > 2σ(I)
Tmin = 0.942, Tmax = 0.964Rint = 0.053
7030 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.128H-atom parameters constrained
S = 1.10Δρmax = 0.28 e Å3
1661 reflectionsΔρmin = 0.33 e Å3
128 parameters
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
xyzUiso*/Ueq
S10.43518 (5)1.09305 (10)0.65529 (4)0.0256 (3)
O10.30541 (12)0.7504 (3)0.68093 (12)0.0210 (4)
N10.19647 (17)0.6825 (3)0.52644 (14)0.0265 (5)
N20.26743 (17)0.8685 (3)0.51955 (14)0.0242 (5)
C10.2073 (2)0.3923 (4)0.77192 (18)0.0278 (6)
H10.25680.49390.81550.033*
C20.1655 (2)0.2040 (4)0.81204 (19)0.0292 (6)
H20.18690.17620.88340.035*
C30.0925 (2)0.0563 (4)0.7481 (2)0.0291 (6)
H30.06570.07400.77570.035*
C40.0589 (2)0.0987 (4)0.64463 (19)0.0278 (6)
H40.00710.00010.60160.033*
C50.1004 (2)0.2843 (4)0.60345 (18)0.0258 (6)
H50.07780.31230.53220.031*
C60.17557 (19)0.4300 (4)0.66720 (17)0.0185 (6)
C70.22137 (19)0.6207 (4)0.62076 (17)0.0193 (6)
C80.3285 (2)0.8996 (4)0.61119 (17)0.0214 (6)
C90.4184 (2)1.2482 (4)0.53652 (18)0.0235 (6)
H9A0.42741.14450.48170.028*
H9B0.34171.31450.51660.028*
C100.5064 (2)1.4340 (4)0.55008 (17)0.0216 (6)
H10A0.58291.36740.57050.026*
H10B0.49701.53780.60480.026*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0253 (4)0.0301 (5)0.0194 (4)0.0069 (3)0.0015 (3)0.0035 (2)
O10.0202 (9)0.0232 (9)0.0192 (9)0.0025 (7)0.0038 (7)0.0028 (6)
N10.0304 (12)0.0260 (12)0.0215 (11)0.0067 (10)0.0035 (9)0.0009 (9)
N20.0293 (12)0.0238 (11)0.0191 (11)0.0046 (9)0.0056 (9)0.0011 (8)
C10.0193 (14)0.0368 (16)0.0239 (14)0.0036 (11)0.0014 (11)0.0017 (10)
C20.0258 (14)0.0363 (16)0.0244 (13)0.0007 (12)0.0039 (11)0.0127 (11)
C30.0250 (14)0.0234 (13)0.0418 (16)0.0021 (11)0.0138 (12)0.0038 (11)
C40.0325 (16)0.0220 (14)0.0316 (15)0.0059 (11)0.0129 (12)0.0073 (10)
C50.0288 (14)0.0296 (15)0.0207 (13)0.0018 (11)0.0093 (11)0.0062 (10)
C60.0180 (13)0.0179 (13)0.0214 (12)0.0033 (10)0.0084 (10)0.0013 (9)
C70.0160 (13)0.0238 (14)0.0171 (12)0.0010 (10)0.0020 (10)0.0039 (9)
C80.0202 (13)0.0241 (14)0.0196 (12)0.0000 (10)0.0045 (10)0.0019 (9)
C90.0249 (13)0.0244 (13)0.0199 (12)0.0010 (11)0.0031 (10)0.0054 (10)
C100.0225 (13)0.0212 (13)0.0199 (13)0.0021 (10)0.0031 (10)0.0018 (9)
Geometric parameters (Å, º) top
S1—C81.729 (2)C3—H30.9500
S1—C91.818 (2)C4—C51.384 (3)
O1—C81.371 (3)C4—H40.9500
O1—C71.378 (3)C5—C61.396 (3)
N1—C71.290 (3)C5—H50.9500
N1—N21.419 (3)C6—C71.468 (3)
N2—C81.295 (3)C9—C101.518 (3)
C1—C21.391 (3)C9—H9A0.9900
C1—C61.392 (3)C9—H9B0.9900
C1—H10.9500C10—C10i1.539 (4)
C2—C31.390 (4)C10—H10A0.9900
C2—H20.9500C10—H10B0.9900
C3—C41.382 (3)
C8—S1—C996.73 (11)C1—C6—C7121.2 (2)
C8—O1—C7101.66 (17)C5—C6—C7118.3 (2)
C7—N1—N2106.53 (18)N1—C7—O1112.81 (19)
C8—N2—N1105.48 (18)N1—C7—C6128.2 (2)
C2—C1—C6119.2 (2)O1—C7—C6118.9 (2)
C2—C1—H1120.4N2—C8—O1113.5 (2)
C6—C1—H1120.4N2—C8—S1129.42 (18)
C3—C2—C1120.2 (2)O1—C8—S1117.02 (17)
C3—C2—H2119.9C10—C9—S1109.62 (17)
C1—C2—H2119.9C10—C9—H9A109.7
C4—C3—C2120.2 (2)S1—C9—H9A109.7
C4—C3—H3119.9C10—C9—H9B109.7
C2—C3—H3119.9S1—C9—H9B109.7
C3—C4—C5120.3 (2)H9A—C9—H9B108.2
C3—C4—H4119.9C9—C10—C10i110.2 (2)
C5—C4—H4119.9C9—C10—H10A109.6
C4—C5—C6119.6 (2)C10i—C10—H10A109.6
C4—C5—H5120.2C9—C10—H10B109.6
C6—C5—H5120.2C10i—C10—H10B109.6
C1—C6—C5120.5 (2)H10A—C10—H10B108.1
C7—N1—N2—C80.1 (2)C1—C6—C7—N1176.7 (2)
C6—C1—C2—C30.4 (4)C5—C6—C7—N14.3 (4)
C1—C2—C3—C41.5 (4)C1—C6—C7—O16.5 (3)
C2—C3—C4—C52.0 (4)C5—C6—C7—O1172.54 (19)
C3—C4—C5—C60.6 (4)N1—N2—C8—O10.1 (3)
C2—C1—C6—C51.8 (3)N1—N2—C8—S1177.74 (17)
C2—C1—C6—C7177.2 (2)C7—O1—C8—N20.0 (2)
C4—C5—C6—C11.3 (3)C7—O1—C8—S1178.11 (15)
C4—C5—C6—C7177.7 (2)C9—S1—C8—N26.4 (2)
N2—N1—C7—O10.1 (2)C9—S1—C8—O1175.89 (17)
N2—N1—C7—C6177.1 (2)C8—S1—C9—C10178.33 (17)
C8—O1—C7—N10.1 (2)S1—C9—C10—C10i179.7 (2)
C8—O1—C7—C6177.40 (19)
Symmetry code: (i) x+1, y+3, z+1.

Experimental details

Crystal data
Chemical formulaC20H18N4O2S2
Mr410.50
Crystal system, space groupMonoclinic, P21/c
Temperature (K)113
a, b, c (Å)12.202 (2), 5.9317 (12), 13.518 (3)
β (°) 104.04 (3)
V3)949.2 (3)
Z2
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.20 × 0.18 × 0.12
Data collection
DiffractometerRigaku Saturn CCD area-detector
diffractometer
Absorption correctionMulti-scan
(CrystalClear; Rigaku/MSC, 2005)
Tmin, Tmax0.942, 0.964
No. of measured, independent and
observed [I > 2σ(I)] reflections
7030, 1661, 1323
Rint0.053
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.128, 1.10
No. of reflections1661
No. of parameters128
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.28, 0.33

Computer programs: CrystalClear (Rigaku/MSC, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

 

Acknowledgements

We gratefully acknowledge support of this project by the Key Laboratory Project of Liaoning Province (No. 2008S127) and by the Doctoral Starting Foundation of Liaoning Province (No. 20071103).

References

First citationBentiss, F., Traisnel, M. & Lagrenee, M. (2000). Corros. Sci. 42, 127–146.  Web of Science CrossRef CAS
First citationHughes, G. & Bryce, M. R. (2005). J. Mater. Chem. 15, 94–107.  Web of Science CrossRef CAS
First citationNavidpour, L., Shafaroodi, H., Abdi, K., Amini, M., Ghahremani, M. H., Dehpour, A. R. & Shafiee, A. (2006). Bioorg. Med. Chem. 14, 2507–2517.  Web of Science CrossRef PubMed CAS
First citationRigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan.
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals

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