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

In the distorted W-shaped mol-ecule of the title compound, C(17)H(12)N(6)O(3)S(2), a twofold axis passes through the carbonyl group. The mol-ecules stack in the crystal through π-π inter-actions [centroid-centroid distance = 3.883 Å] and weak C-H⋯N hydrogen-bonding inter-actions, forming a three-dimensional architecture.

Related literature

For the use of oxadiazole-containing compounds with symmetrical or asymmetrical structures in coordination chemistry, see: Du et al. (2006 ▶); Fang et al. (2002 ▶); Wu et al. (2010 ▶); Ye et al. (2007 ▶). For a similar propanone-bridged dithio­ether compound, see: Wu et al. (2005 ▶).

Experimental

Crystal data

C17H12N6O3S2

M = 412.45

Monoclinic,

a = 14.266 (3) Å

b = 7.8342 (16) Å

c = 16.703 (3) Å

β = 100.25 (3)°

V = 1837.0 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.32 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Siemens SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.913, T max = 1.000

8929 measured reflections

1607 independent reflections

1448 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.076

wR(F 2) = 0.134

S = 1.24

1607 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.21 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1994 ▶); data reduction: SAINT; 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: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811001140/hg2787sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811001140/hg2787Isup2.hkl

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

C17H12N6O3S2	F(000) = 848
Mr = 412.45	Dx = 1.491 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2643 reflections
a = 14.266 (3) Å	θ = 2.5–29.1°
b = 7.8342 (16) Å	µ = 0.32 mm−1
c = 16.703 (3) Å	T = 293 K
β = 100.25 (3)°	Block, yellow
V = 1837.0 (6) Å3	0.20 × 0.20 × 0.20 mm
Z = 4

Siemens SMART CCD diffractometer	1607 independent reflections
Radiation source: fine-focus sealed tube	1448 reflections with I > 2σ(I)
graphite	Rint = 0.050
ω scans	θmax = 25.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −16→16
Tmin = 0.913, Tmax = 1.000	k = −9→9
8929 measured reflections	l = −19→19

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)] = 0.076	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.134	H-atom parameters constrained
S = 1.24	w = 1/[σ2(Fo2) + (0.0357P)2 + 3.0521P] where P = (Fo2 + 2Fc2)/3
1607 reflections	(Δ/σ)max < 0.001
128 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.21 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	0.19304 (8)	0.68102 (19)	0.24214 (6)	0.0785 (5)
O1	0.0000	0.5351 (5)	0.2500	0.0640 (11)
O2	0.28820 (16)	0.5281 (3)	0.37180 (14)	0.0525 (7)
N1	0.1587 (2)	0.6557 (4)	0.39768 (17)	0.0485 (8)
N2	0.2056 (2)	0.5752 (4)	0.46924 (17)	0.0488 (8)
N3	0.4202 (2)	0.3330 (4)	0.46674 (18)	0.0549 (8)
C1	0.0000	0.6876 (7)	0.2500	0.0453 (12)
C2	0.0834 (2)	0.7944 (5)	0.2358 (2)	0.0531 (10)
H2A	0.0928	0.8879	0.2763	0.064*
H2B	0.0675	0.8471	0.1812	0.064*
C3	0.2100 (2)	0.6238 (5)	0.3439 (2)	0.0472 (9)
C4	0.2798 (2)	0.5024 (4)	0.45132 (19)	0.0394 (8)
C5	0.3528 (2)	0.4016 (4)	0.5029 (2)	0.0431 (8)
C6	0.3488 (3)	0.3797 (5)	0.5839 (2)	0.0500 (9)
H6	0.2993	0.4304	0.6070	0.060*
C7	0.4183 (3)	0.2824 (5)	0.6308 (2)	0.0587 (10)
H7	0.4172	0.2635	0.6868	0.070*
C8	0.4890 (3)	0.2137 (5)	0.5952 (3)	0.0610 (11)
H8	0.5382	0.1475	0.6263	0.073*
C9	0.4878 (3)	0.2419 (5)	0.5144 (3)	0.0637 (11)
H9	0.5375	0.1942	0.4905	0.076*

	U11	U22	U33	U12	U13	U23
S1	0.0624 (7)	0.1289 (11)	0.0478 (6)	0.0273 (7)	0.0196 (5)	0.0245 (7)
O1	0.076 (3)	0.053 (3)	0.056 (2)	0.000	−0.0065 (19)	0.000
O2	0.0435 (14)	0.0728 (18)	0.0427 (14)	0.0122 (12)	0.0115 (11)	0.0052 (12)
N1	0.0445 (17)	0.059 (2)	0.0407 (16)	0.0085 (14)	0.0045 (13)	−0.0009 (14)
N2	0.0510 (18)	0.058 (2)	0.0365 (16)	0.0064 (15)	0.0064 (13)	−0.0037 (14)
N3	0.0491 (18)	0.066 (2)	0.0516 (18)	0.0100 (16)	0.0151 (15)	0.0038 (16)
C1	0.060 (3)	0.047 (3)	0.024 (2)	0.000	−0.006 (2)	0.000
C2	0.052 (2)	0.064 (3)	0.041 (2)	0.0022 (19)	0.0029 (16)	0.0107 (18)
C3	0.0380 (19)	0.059 (2)	0.044 (2)	0.0037 (17)	0.0061 (16)	0.0031 (18)
C4	0.0417 (19)	0.044 (2)	0.0327 (17)	−0.0036 (15)	0.0077 (14)	−0.0048 (15)
C5	0.0433 (19)	0.042 (2)	0.0431 (19)	−0.0034 (16)	0.0068 (16)	−0.0051 (16)
C6	0.054 (2)	0.054 (2)	0.042 (2)	0.0065 (18)	0.0084 (17)	−0.0068 (18)
C7	0.067 (3)	0.060 (3)	0.047 (2)	0.005 (2)	0.0047 (19)	0.0036 (19)
C8	0.054 (2)	0.058 (3)	0.067 (3)	0.006 (2)	0.000 (2)	0.017 (2)
C9	0.049 (2)	0.070 (3)	0.074 (3)	0.015 (2)	0.017 (2)	0.012 (2)

S1—C3	1.732 (4)	C2—H2A	0.9900
S1—C2	1.785 (4)	C2—H2B	0.9900
O1—C1	1.195 (6)	C4—C5	1.460 (5)
O2—C3	1.356 (4)	C5—C6	1.374 (5)
O2—C4	1.369 (4)	C6—C7	1.379 (5)
N1—C3	1.281 (4)	C6—H6	0.9500
N1—N2	1.411 (4)	C7—C8	1.369 (5)
N2—C4	1.283 (4)	C7—H7	0.9500
N3—C5	1.336 (4)	C8—C9	1.365 (6)
N3—C9	1.341 (5)	C8—H8	0.9500
C1—C2	1.507 (5)	C9—H9	0.9500
C1—C2i	1.507 (5)
C3—S1—C2	98.92 (17)	N2—C4—C5	129.3 (3)
C3—O2—C4	101.9 (2)	O2—C4—C5	118.4 (3)
C3—N1—N2	105.2 (3)	N3—C5—C6	123.6 (3)
C4—N2—N1	106.7 (3)	N3—C5—C4	116.5 (3)
C5—N3—C9	116.4 (3)	C6—C5—C4	119.9 (3)
O1—C1—C2	123.7 (2)	C5—C6—C7	118.5 (3)
O1—C1—C2i	123.7 (2)	C5—C6—H6	120.8
C2—C1—C2i	112.6 (5)	C7—C6—H6	120.8
C1—C2—S1	115.0 (3)	C8—C7—C6	118.8 (4)
C1—C2—H2A	108.5	C8—C7—H7	120.6
S1—C2—H2A	108.5	C6—C7—H7	120.6
C1—C2—H2B	108.5	C9—C8—C7	119.0 (4)
S1—C2—H2B	108.5	C9—C8—H8	120.5
H2A—C2—H2B	107.5	C7—C8—H8	120.5
N1—C3—O2	113.9 (3)	N3—C9—C8	123.7 (4)
N1—C3—S1	129.8 (3)	N3—C9—H9	118.2
O2—C3—S1	116.3 (2)	C8—C9—H9	118.2
N2—C4—O2	112.3 (3)
C3—N1—N2—C4	−0.3 (4)	C3—O2—C4—C5	179.9 (3)
O1—C1—C2—S1	−13.9 (3)	C9—N3—C5—C6	−1.6 (5)
C2i—C1—C2—S1	166.1 (3)	C9—N3—C5—C4	179.3 (3)
C3—S1—C2—C1	−64.4 (3)	N2—C4—C5—N3	176.6 (3)
N2—N1—C3—O2	0.1 (4)	O2—C4—C5—N3	−3.8 (5)
N2—N1—C3—S1	178.8 (3)	N2—C4—C5—C6	−2.5 (6)
C4—O2—C3—N1	0.2 (4)	O2—C4—C5—C6	177.1 (3)
C4—O2—C3—S1	−178.8 (2)	N3—C5—C6—C7	0.4 (6)
C2—S1—C3—N1	−0.5 (4)	C4—C5—C6—C7	179.4 (3)
C2—S1—C3—O2	178.3 (3)	C5—C6—C7—C8	0.9 (6)
N1—N2—C4—O2	0.5 (4)	C6—C7—C8—C9	−0.8 (6)
N1—N2—C4—C5	−179.8 (3)	C5—N3—C9—C8	1.7 (6)
C3—O2—C4—N2	−0.4 (4)	C7—C8—C9—N3	−0.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2B···N3ii	0.99	2.51	3.388 (4)	148
C9—H9···N1iii	0.95	2.54	3.449 (5)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2B⋯N3i	0.99	2.51	3.388 (4)	148
C9—H9⋯N1ii	0.95	2.54	3.449 (5)	161

Symmetry codes: (i) ; (ii) .