![](/logos/buttonlogos/cross.png)
![](/logos/buttonlogos/cross.png)
organic compounds
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
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); Hughes & Bryce (2005
); Navidpour et al. (2006
).
Experimental
Crystal data
|
Data collection: CrystalClear (Rigaku/MSC, 2005); cell CrystalClear; data reduction: CrystalClear; 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.
Supporting information
https://doi.org/10.1107/S1600536810042315/zs2072sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810042315/zs2072Isup2.hkl
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).
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).
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 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].
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 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 ofFunctionalized 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).
Data collection: CrystalClear (Rigaku/MSC, 2005); cell
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).C20H18N4O2S2 | F(000) = 428 |
Mr = 410.50 | Dx = 1.436 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 3017 reflections |
a = 12.202 (2) Å | θ = 1.7–27.9° |
b = 5.9317 (12) Å | µ = 0.31 mm−1 |
c = 13.518 (3) Å | T = 113 K |
β = 104.04 (3)° | Prism, colorless |
V = 949.2 (3) Å3 | 0.20 × 0.18 × 0.12 mm |
Z = 2 |
Rigaku Saturn CCD area-detector diffractometer | 1661 independent reflections |
Radiation source: rotating anode | 1323 reflections with I > 2σ(I) |
Confocal monochromator | Rint = 0.053 |
Detector resolution: 7.31 pixels mm-1 | θmax = 25.0°, θmin = 1.7° |
φ and ω scans | h = −12→14 |
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005) | k = −7→6 |
Tmin = 0.942, Tmax = 0.964 | l = −16→16 |
7030 measured reflections |
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)] = 0.040 | H-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 reflections | Δρmax = 0.28 e Å−3 |
128 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.067 (10) |
C20H18N4O2S2 | V = 949.2 (3) Å3 |
Mr = 410.50 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 12.202 (2) Å | µ = 0.31 mm−1 |
b = 5.9317 (12) Å | T = 113 K |
c = 13.518 (3) Å | 0.20 × 0.18 × 0.12 mm |
β = 104.04 (3)° |
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 = 0.964 | Rint = 0.053 |
7030 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.10 | Δρmax = 0.28 e Å−3 |
1661 reflections | Δρmin = −0.33 e Å−3 |
128 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
S1 | 0.43518 (5) | 1.09305 (10) | 0.65529 (4) | 0.0256 (3) | |
O1 | 0.30541 (12) | 0.7504 (3) | 0.68093 (12) | 0.0210 (4) | |
N1 | 0.19647 (17) | 0.6825 (3) | 0.52644 (14) | 0.0265 (5) | |
N2 | 0.26743 (17) | 0.8685 (3) | 0.51955 (14) | 0.0242 (5) | |
C1 | 0.2073 (2) | 0.3923 (4) | 0.77192 (18) | 0.0278 (6) | |
H1 | 0.2568 | 0.4939 | 0.8155 | 0.033* | |
C2 | 0.1655 (2) | 0.2040 (4) | 0.81204 (19) | 0.0292 (6) | |
H2 | 0.1869 | 0.1762 | 0.8834 | 0.035* | |
C3 | 0.0925 (2) | 0.0563 (4) | 0.7481 (2) | 0.0291 (6) | |
H3 | 0.0657 | −0.0740 | 0.7757 | 0.035* | |
C4 | 0.0589 (2) | 0.0987 (4) | 0.64463 (19) | 0.0278 (6) | |
H4 | 0.0071 | −0.0001 | 0.6016 | 0.033* | |
C5 | 0.1004 (2) | 0.2843 (4) | 0.60345 (18) | 0.0258 (6) | |
H5 | 0.0778 | 0.3123 | 0.5322 | 0.031* | |
C6 | 0.17557 (19) | 0.4300 (4) | 0.66720 (17) | 0.0185 (6) | |
C7 | 0.22137 (19) | 0.6207 (4) | 0.62076 (17) | 0.0193 (6) | |
C8 | 0.3285 (2) | 0.8996 (4) | 0.61119 (17) | 0.0214 (6) | |
C9 | 0.4184 (2) | 1.2482 (4) | 0.53652 (18) | 0.0235 (6) | |
H9A | 0.4274 | 1.1445 | 0.4817 | 0.028* | |
H9B | 0.3417 | 1.3145 | 0.5166 | 0.028* | |
C10 | 0.5064 (2) | 1.4340 (4) | 0.55008 (17) | 0.0216 (6) | |
H10A | 0.5829 | 1.3674 | 0.5705 | 0.026* | |
H10B | 0.4970 | 1.5378 | 0.6048 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0253 (4) | 0.0301 (5) | 0.0194 (4) | −0.0069 (3) | 0.0015 (3) | 0.0035 (2) |
O1 | 0.0202 (9) | 0.0232 (9) | 0.0192 (9) | −0.0025 (7) | 0.0038 (7) | 0.0028 (6) |
N1 | 0.0304 (12) | 0.0260 (12) | 0.0215 (11) | −0.0067 (10) | 0.0035 (9) | −0.0009 (9) |
N2 | 0.0293 (12) | 0.0238 (11) | 0.0191 (11) | −0.0046 (9) | 0.0056 (9) | 0.0011 (8) |
C1 | 0.0193 (14) | 0.0368 (16) | 0.0239 (14) | −0.0036 (11) | −0.0014 (11) | 0.0017 (10) |
C2 | 0.0258 (14) | 0.0363 (16) | 0.0244 (13) | −0.0007 (12) | 0.0039 (11) | 0.0127 (11) |
C3 | 0.0250 (14) | 0.0234 (13) | 0.0418 (16) | 0.0021 (11) | 0.0138 (12) | 0.0038 (11) |
C4 | 0.0325 (16) | 0.0220 (14) | 0.0316 (15) | −0.0059 (11) | 0.0129 (12) | −0.0073 (10) |
C5 | 0.0288 (14) | 0.0296 (15) | 0.0207 (13) | −0.0018 (11) | 0.0093 (11) | −0.0062 (10) |
C6 | 0.0180 (13) | 0.0179 (13) | 0.0214 (12) | 0.0033 (10) | 0.0084 (10) | −0.0013 (9) |
C7 | 0.0160 (13) | 0.0238 (14) | 0.0171 (12) | 0.0010 (10) | 0.0020 (10) | −0.0039 (9) |
C8 | 0.0202 (13) | 0.0241 (14) | 0.0196 (12) | 0.0000 (10) | 0.0045 (10) | 0.0019 (9) |
C9 | 0.0249 (13) | 0.0244 (13) | 0.0199 (12) | −0.0010 (11) | 0.0031 (10) | 0.0054 (10) |
C10 | 0.0225 (13) | 0.0212 (13) | 0.0199 (13) | 0.0021 (10) | 0.0031 (10) | −0.0018 (9) |
S1—C8 | 1.729 (2) | C3—H3 | 0.9500 |
S1—C9 | 1.818 (2) | C4—C5 | 1.384 (3) |
O1—C8 | 1.371 (3) | C4—H4 | 0.9500 |
O1—C7 | 1.378 (3) | C5—C6 | 1.396 (3) |
N1—C7 | 1.290 (3) | C5—H5 | 0.9500 |
N1—N2 | 1.419 (3) | C6—C7 | 1.468 (3) |
N2—C8 | 1.295 (3) | C9—C10 | 1.518 (3) |
C1—C2 | 1.391 (3) | C9—H9A | 0.9900 |
C1—C6 | 1.392 (3) | C9—H9B | 0.9900 |
C1—H1 | 0.9500 | C10—C10i | 1.539 (4) |
C2—C3 | 1.390 (4) | C10—H10A | 0.9900 |
C2—H2 | 0.9500 | C10—H10B | 0.9900 |
C3—C4 | 1.382 (3) | ||
C8—S1—C9 | 96.73 (11) | C1—C6—C7 | 121.2 (2) |
C8—O1—C7 | 101.66 (17) | C5—C6—C7 | 118.3 (2) |
C7—N1—N2 | 106.53 (18) | N1—C7—O1 | 112.81 (19) |
C8—N2—N1 | 105.48 (18) | N1—C7—C6 | 128.2 (2) |
C2—C1—C6 | 119.2 (2) | O1—C7—C6 | 118.9 (2) |
C2—C1—H1 | 120.4 | N2—C8—O1 | 113.5 (2) |
C6—C1—H1 | 120.4 | N2—C8—S1 | 129.42 (18) |
C3—C2—C1 | 120.2 (2) | O1—C8—S1 | 117.02 (17) |
C3—C2—H2 | 119.9 | C10—C9—S1 | 109.62 (17) |
C1—C2—H2 | 119.9 | C10—C9—H9A | 109.7 |
C4—C3—C2 | 120.2 (2) | S1—C9—H9A | 109.7 |
C4—C3—H3 | 119.9 | C10—C9—H9B | 109.7 |
C2—C3—H3 | 119.9 | S1—C9—H9B | 109.7 |
C3—C4—C5 | 120.3 (2) | H9A—C9—H9B | 108.2 |
C3—C4—H4 | 119.9 | C9—C10—C10i | 110.2 (2) |
C5—C4—H4 | 119.9 | C9—C10—H10A | 109.6 |
C4—C5—C6 | 119.6 (2) | C10i—C10—H10A | 109.6 |
C4—C5—H5 | 120.2 | C9—C10—H10B | 109.6 |
C6—C5—H5 | 120.2 | C10i—C10—H10B | 109.6 |
C1—C6—C5 | 120.5 (2) | H10A—C10—H10B | 108.1 |
C7—N1—N2—C8 | 0.1 (2) | C1—C6—C7—N1 | −176.7 (2) |
C6—C1—C2—C3 | −0.4 (4) | C5—C6—C7—N1 | 4.3 (4) |
C1—C2—C3—C4 | −1.5 (4) | C1—C6—C7—O1 | 6.5 (3) |
C2—C3—C4—C5 | 2.0 (4) | C5—C6—C7—O1 | −172.54 (19) |
C3—C4—C5—C6 | −0.6 (4) | N1—N2—C8—O1 | −0.1 (3) |
C2—C1—C6—C5 | 1.8 (3) | N1—N2—C8—S1 | 177.74 (17) |
C2—C1—C6—C7 | −177.2 (2) | C7—O1—C8—N2 | 0.0 (2) |
C4—C5—C6—C1 | −1.3 (3) | C7—O1—C8—S1 | −178.11 (15) |
C4—C5—C6—C7 | 177.7 (2) | C9—S1—C8—N2 | 6.4 (2) |
N2—N1—C7—O1 | −0.1 (2) | C9—S1—C8—O1 | −175.89 (17) |
N2—N1—C7—C6 | −177.1 (2) | C8—S1—C9—C10 | −178.33 (17) |
C8—O1—C7—N1 | 0.1 (2) | S1—C9—C10—C10i | 179.7 (2) |
C8—O1—C7—C6 | 177.40 (19) |
Symmetry code: (i) −x+1, −y+3, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C20H18N4O2S2 |
Mr | 410.50 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 113 |
a, b, c (Å) | 12.202 (2), 5.9317 (12), 13.518 (3) |
β (°) | 104.04 (3) |
V (Å3) | 949.2 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.20 × 0.18 × 0.12 |
Data collection | |
Diffractometer | Rigaku Saturn CCD area-detector |
Absorption correction | Multi-scan (CrystalClear; Rigaku/MSC, 2005) |
Tmin, Tmax | 0.942, 0.964 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7030, 1661, 1323 |
Rint | 0.053 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.128, 1.10 |
No. of reflections | 1661 |
No. of parameters | 128 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 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
Bentiss, F., Traisnel, M. & Lagrenee, M. (2000). Corros. Sci. 42, 127–146. Web of Science CrossRef CAS Google Scholar
Hughes, G. & Bryce, M. R. (2005). J. Mater. Chem. 15, 94–107. Web of Science CrossRef CAS Google Scholar
Navidpour, 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 Google Scholar
Rigaku/MSC (2005). CrystalClear. Molecular Structure Corporation, The Woodlands, Texas, USA, and Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
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].