5,5'-Diphenyl-2,2'-[butane-1,4-diylbis(sulfanedi-yl)]bis-(1,3,4-oxadiazole).

The complete mol-ecule of the title compound, C(20)H(18)N(4)O(2)S(2), 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

C20H18N4O2S2

M = 410.50

Monoclinic,

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 ▶) T min = 0.942, T max = 0.964

7030 measured reflections

1661 independent reflections

1323 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 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 ▶); cell refinement: 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810042315/zs2072sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810042315/zs2072Isup2.hkl

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

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	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)

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)