1,4-Bis{[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]sulfan-yl}butane.

In the centrosymmetric title compound, C(18)H(16)N(6)O(2)S(2), the 1,3,4-oxadiazole and the attached pyridinyl ring are twisted by 5.3 (3)°.

Related literature

For applications of heterocyclic derivatives, see: Al-Talib et al. (1990 ▶); Nakagawa et al. (1996 ▶); Zhang et al. (2007 ▶). For related structuresbn,, see: Wang et al. (2010 ▶, 2011 ▶); Zhao et al. (2010 ▶).

Experimental

Crystal data

C18H16N6O2S2

M = 412.49

Monoclinic,

a = 4.9780 (6) Å

b = 5.7933 (7) Å

c = 31.003 (4) Å

β = 92.588 (5)°

V = 893.20 (18) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 113 K

0.20 × 0.18 × 0.10 mm

Data collection

Rigaku Saturn CCD area-detector diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.937, T max = 0.962

8437 measured reflections

2128 independent reflections

1811 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.10

2128 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.19 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/S1600536811006805/kp2310sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006805/kp2310Isup2.hkl

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

C18H16N6O2S2	F(000) = 428
Mr = 412.49	Dx = 1.534 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2798 reflections
a = 4.9780 (6) Å	θ = 2.6–27.9°
b = 5.7933 (7) Å	µ = 0.33 mm−1
c = 31.003 (4) Å	T = 113 K
β = 92.588 (5)°	Prism, light-yellow
V = 893.20 (18) Å3	0.20 × 0.18 × 0.10 mm
Z = 2

Rigaku Saturn CCD area-detector diffractometer	2128 independent reflections
Radiation source: rotating anode	1811 reflections with I > 2σ(I)
multilayer	Rint = 0.035
Detector resolution: 14.63 pixels mm-1	θmax = 27.9°, θmin = 2.6°
φ and ω scans	h = −4→6
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −7→7
Tmin = 0.937, Tmax = 0.962	l = −38→40
8437 measured reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.089	H-atom parameters constrained
S = 1.10	w = 1/[σ2(Fo2) + (0.0531P)2 + 0.054P] where P = (Fo2 + 2Fc2)/3
2128 reflections	(Δ/σ)max = 0.001
127 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.19 e Å−3

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	0.25227 (6)	0.35176 (5)	0.422550 (9)	0.01776 (12)
O1	0.61211 (17)	0.17771 (15)	0.37253 (3)	0.0163 (2)
N1	1.3455 (2)	−0.0526 (2)	0.27364 (3)	0.0197 (2)
N2	0.7346 (2)	−0.15583 (19)	0.40229 (3)	0.0186 (2)
N3	0.5348 (2)	−0.05632 (19)	0.42735 (3)	0.0189 (2)
C1	1.1858 (3)	0.1307 (2)	0.27715 (4)	0.0190 (3)
H1	1.2063	0.2551	0.2576	0.023*
C2	0.9910 (3)	0.1507 (2)	0.30774 (4)	0.0179 (3)
H2	0.8797	0.2836	0.3086	0.021*
C3	0.9634 (2)	−0.0287 (2)	0.33688 (4)	0.0155 (3)
C4	1.1268 (3)	−0.2220 (2)	0.33375 (4)	0.0185 (3)
H4	1.1125	−0.3479	0.3531	0.022*
C5	1.3118 (3)	−0.2262 (2)	0.30146 (4)	0.0199 (3)
H5	1.4206	−0.3598	0.2990	0.024*
C6	0.7718 (2)	−0.0138 (2)	0.37112 (4)	0.0153 (3)
C7	0.4729 (2)	0.1379 (2)	0.40882 (4)	0.0152 (3)
C8	0.1260 (3)	0.2236 (2)	0.47114 (4)	0.0177 (3)
H8A	0.0331	0.0764	0.4640	0.021*
H8B	0.2770	0.1908	0.4921	0.021*
C9	−0.0695 (3)	0.3927 (2)	0.49063 (4)	0.0178 (3)
H9A	−0.2052	0.4403	0.4680	0.021*
H9B	−0.1652	0.3137	0.5137	0.021*

	U11	U22	U33	U12	U13	U23
S1	0.0216 (2)	0.01715 (19)	0.01492 (18)	0.00366 (11)	0.00549 (12)	0.00101 (11)
O1	0.0174 (4)	0.0179 (5)	0.0140 (4)	0.0017 (3)	0.0045 (3)	0.0003 (3)
N1	0.0180 (5)	0.0223 (6)	0.0191 (5)	−0.0024 (4)	0.0030 (4)	−0.0030 (4)
N2	0.0208 (6)	0.0179 (6)	0.0176 (5)	0.0020 (4)	0.0053 (4)	−0.0002 (4)
N3	0.0201 (5)	0.0193 (6)	0.0177 (5)	0.0022 (4)	0.0053 (4)	−0.0003 (4)
C1	0.0194 (7)	0.0202 (7)	0.0176 (6)	−0.0024 (5)	0.0037 (5)	0.0011 (5)
C2	0.0178 (6)	0.0173 (6)	0.0186 (6)	0.0012 (5)	0.0023 (5)	−0.0005 (5)
C3	0.0146 (6)	0.0185 (6)	0.0132 (5)	−0.0014 (5)	−0.0001 (4)	−0.0016 (4)
C4	0.0205 (6)	0.0185 (6)	0.0166 (6)	0.0009 (5)	0.0022 (5)	0.0009 (5)
C5	0.0193 (6)	0.0200 (6)	0.0207 (6)	0.0025 (5)	0.0029 (5)	−0.0026 (5)
C6	0.0142 (6)	0.0160 (6)	0.0158 (6)	0.0011 (4)	0.0003 (4)	−0.0017 (4)
C7	0.0155 (6)	0.0188 (6)	0.0114 (5)	−0.0013 (4)	0.0028 (4)	−0.0014 (4)
C8	0.0215 (6)	0.0162 (6)	0.0158 (6)	−0.0010 (5)	0.0055 (5)	−0.0007 (5)
C9	0.0173 (6)	0.0182 (6)	0.0183 (6)	−0.0013 (5)	0.0042 (5)	−0.0030 (5)

S1—C7	1.7218 (13)	C2—H2	0.9500
S1—C8	1.8171 (12)	C3—C4	1.3902 (17)
O1—C6	1.3669 (14)	C3—C6	1.4615 (16)
O1—C7	1.3675 (14)	C4—C5	1.3906 (17)
N1—C1	1.3337 (17)	C4—H4	0.9500
N1—C5	1.3404 (17)	C5—H5	0.9500
N2—C6	1.2888 (16)	C8—C9	1.5251 (17)
N2—N3	1.4121 (15)	C8—H8A	0.9900
N3—C7	1.2941 (16)	C8—H8B	0.9900
C1—C2	1.3914 (18)	C9—C9i	1.525 (2)
C1—H1	0.9500	C9—H9A	0.9900
C2—C3	1.3878 (17)	C9—H9B	0.9900
C7—S1—C8	99.16 (6)	C4—C5—H5	118.1
C6—O1—C7	101.91 (9)	N2—C6—O1	113.00 (10)
C1—N1—C5	116.91 (11)	N2—C6—C3	128.89 (11)
C6—N2—N3	106.29 (10)	O1—C6—C3	118.07 (10)
C7—N3—N2	105.69 (10)	N3—C7—O1	113.10 (11)
N1—C1—C2	123.91 (12)	N3—C7—S1	131.13 (10)
N1—C1—H1	118.0	O1—C7—S1	115.76 (9)
C2—C1—H1	118.0	C9—C8—S1	108.47 (9)
C3—C2—C1	118.29 (12)	C9—C8—H8A	110.0
C3—C2—H2	120.9	S1—C8—H8A	110.0
C1—C2—H2	120.9	C9—C8—H8B	110.0
C2—C3—C4	118.84 (11)	S1—C8—H8B	110.0
C2—C3—C6	121.06 (11)	H8A—C8—H8B	108.4
C4—C3—C6	120.08 (11)	C9i—C9—C8	112.82 (13)
C3—C4—C5	118.21 (12)	C9i—C9—H9A	109.0
C3—C4—H4	120.9	C8—C9—H9A	109.0
C5—C4—H4	120.9	C9i—C9—H9B	109.0
N1—C5—C4	123.80 (12)	C8—C9—H9B	109.0
N1—C5—H5	118.1	H9A—C9—H9B	107.8
C6—N2—N3—C7	−0.50 (14)	C2—C3—C6—N2	−174.70 (13)
C5—N1—C1—C2	0.29 (19)	C4—C3—C6—N2	3.7 (2)
N1—C1—C2—C3	1.2 (2)	C2—C3—C6—O1	2.71 (17)
C1—C2—C3—C4	−1.37 (19)	C4—C3—C6—O1	−178.93 (11)
C1—C2—C3—C6	177.01 (11)	N2—N3—C7—O1	0.93 (14)
C2—C3—C4—C5	0.23 (18)	N2—N3—C7—S1	−177.95 (10)
C6—C3—C4—C5	−178.17 (11)	C6—O1—C7—N3	−0.96 (13)
C1—N1—C5—C4	−1.56 (19)	C6—O1—C7—S1	178.10 (8)
C3—C4—C5—N1	1.3 (2)	C8—S1—C7—N3	−0.56 (14)
N3—N2—C6—O1	−0.09 (14)	C8—S1—C7—O1	−179.42 (9)
N3—N2—C6—C3	177.42 (12)	C7—S1—C8—C9	177.46 (9)
C7—O1—C6—N2	0.61 (13)	S1—C8—C9—C9i	−69.35 (15)
C7—O1—C6—C3	−177.20 (11)