5,5'-Di-4-pyridyl-2,2'-(p-phenyl-ene)di-1,3,4-oxadiazole.

In the crystal structure of the title compound, C(20)H(12)N(6)O(2), the mol-ecules are located on centres of inversion. The complete mol-ecule is almost planar, with a maximum deviation from the mean plane of 0.0657 (1) Å for the O atom. In the crystal, mol-ecules are stacked into columns elongated in the a axis direction. The centroid-centroid distances between the aromatic rings of the mol-ecules within the columns are 3.6406 (1) and 3.6287 (2) Å. Mol-ecules are additionally connected via weak inter-molecular C-H⋯N hydrogen bonding.

Related literature

For the potential uses of oxadiazo­les, see: Bentiss et al. (2000 ▶); Navidpour et al. (2006 ▶). For related studies on oxadiazo­les, see: Wang et al. (2005 ▶); Zhang et al. (2007 ▶). For the synthesis of bis-1,3,4-oxadiazol, see: Al-Talib et al. (1990 ▶).

Experimental

Crystal data

C20H12N6O2

M = 368.36

Monoclinic,

a = 6.2424 (6) Å

b = 7.6969 (7) Å

c = 17.7321 (16) Å

β = 96.635 (2)°

V = 846.27 (14) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 183 K

0.30 × 0.18 × 0.15 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.971, T max = 0.985

4541 measured reflections

1665 independent reflections

1114 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.112

S = 1.01

1665 reflections

151 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.18 e Å−3

Δρmin = −0.13 e Å−3

Data collection: SMART (Bruker, 1999 ▶); cell refinement: SAINT (Bruker, 1999 ▶); 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/S1600536809050557/nc2169sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809050557/nc2169Isup2.hkl

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

C20H12N6O2	F(000) = 380
Mr = 368.36	Dx = 1.446 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 6.2424 (6) Å	θ = 2.3–26.1°
b = 7.6969 (7) Å	µ = 0.10 mm−1
c = 17.7321 (16) Å	T = 183 K
β = 96.635 (2)°	Needle, yellow
V = 846.27 (14) Å3	0.30 × 0.18 × 0.15 mm
Z = 2

Bruker SMART APEX CCD diffractometer	1665 independent reflections
Radiation source: fine-focus sealed tube	1114 reflections with I > 2σ(I)
graphite	Rint = 0.028
ω scans	θmax = 26.1°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −5→7
Tmin = 0.971, Tmax = 0.985	k = −9→6
4541 measured reflections	l = −21→20

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0489P)2 + 0.1652P] where P = (Fo2 + 2Fc2)/3
1665 reflections	(Δ/σ)max = 0.001
151 parameters	Δρmax = 0.18 e Å−3
0 restraints	Δρmin = −0.13 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
O1	1.0105 (2)	0.26943 (17)	0.91503 (7)	0.0455 (4)
N1	1.0141 (3)	0.2372 (2)	1.03852 (9)	0.0481 (5)
N2	0.8290 (3)	0.1534 (2)	1.00208 (9)	0.0490 (5)
C2	1.3123 (3)	0.4031 (2)	0.99232 (11)	0.0393 (5)
C6	0.6794 (3)	0.1193 (3)	0.86751 (11)	0.0427 (5)
C4	1.1139 (3)	0.3024 (2)	0.98550 (10)	0.0406 (5)
C5	0.8350 (3)	0.1759 (2)	0.93029 (11)	0.0419 (5)
C1	1.4231 (3)	0.4324 (3)	1.06365 (12)	0.0445 (5)
C3	1.3910 (3)	0.4712 (3)	0.92850 (11)	0.0436 (5)
N3	0.3677 (3)	0.0203 (3)	0.75019 (11)	0.0710 (6)
C10	0.5034 (4)	0.0236 (3)	0.88153 (14)	0.0559 (6)
C7	0.6983 (4)	0.1636 (3)	0.79320 (13)	0.0578 (6)
C8	0.5402 (4)	0.1127 (4)	0.73749 (14)	0.0672 (7)
C9	0.3534 (4)	−0.0212 (4)	0.82157 (14)	0.0673 (7)
H2	1.316 (3)	0.452 (2)	0.8803 (12)	0.048 (5)*
H1	1.365 (3)	0.390 (2)	1.1064 (12)	0.046 (6)*
H3	0.483 (3)	−0.009 (3)	0.9316 (13)	0.063 (7)*
H6	0.550 (4)	0.142 (3)	0.6864 (15)	0.085 (8)*
H5	0.812 (4)	0.222 (3)	0.7800 (13)	0.069 (8)*
H4	0.234 (4)	−0.079 (3)	0.8314 (14)	0.086 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0404 (8)	0.0544 (9)	0.0408 (8)	−0.0085 (6)	0.0005 (6)	−0.0010 (6)
N1	0.0434 (10)	0.0573 (11)	0.0424 (9)	−0.0076 (8)	−0.0004 (8)	−0.0024 (8)
N2	0.0453 (10)	0.0571 (11)	0.0434 (10)	−0.0091 (8)	0.0001 (8)	−0.0006 (8)
C2	0.0336 (10)	0.0411 (11)	0.0419 (11)	0.0023 (8)	−0.0017 (8)	−0.0022 (8)
C6	0.0395 (11)	0.0451 (12)	0.0425 (11)	−0.0004 (9)	0.0001 (9)	−0.0044 (9)
C4	0.0389 (11)	0.0445 (12)	0.0367 (10)	0.0018 (9)	−0.0027 (9)	−0.0033 (9)
C5	0.0362 (11)	0.0428 (11)	0.0463 (12)	−0.0027 (9)	0.0026 (9)	−0.0004 (9)
C1	0.0423 (12)	0.0521 (13)	0.0383 (11)	−0.0018 (10)	0.0012 (9)	0.0029 (10)
C3	0.0399 (12)	0.0509 (12)	0.0377 (11)	0.0003 (9)	−0.0054 (9)	−0.0013 (9)
N3	0.0657 (14)	0.0925 (16)	0.0512 (12)	−0.0132 (12)	−0.0083 (10)	−0.0080 (11)
C10	0.0573 (14)	0.0641 (15)	0.0452 (13)	−0.0159 (11)	0.0012 (11)	0.0002 (11)
C7	0.0552 (14)	0.0711 (16)	0.0464 (13)	−0.0106 (12)	0.0028 (11)	0.0003 (11)
C8	0.0718 (17)	0.0867 (19)	0.0414 (13)	−0.0059 (14)	−0.0007 (12)	0.0022 (12)
C9	0.0559 (16)	0.088 (2)	0.0559 (16)	−0.0232 (14)	−0.0020 (12)	−0.0079 (13)

O1—C4	1.362 (2)	C1—H1	0.94 (2)
O1—C5	1.364 (2)	C3—C1i	1.371 (3)
N1—C4	1.288 (2)	C3—H2	0.94 (2)
N1—N2	1.413 (2)	N3—C9	1.319 (3)
N2—C5	1.290 (2)	N3—C8	1.331 (3)
C2—C3	1.387 (3)	C10—C9	1.377 (3)
C2—C1	1.388 (3)	C10—H3	0.95 (2)
C2—C4	1.454 (3)	C7—C8	1.370 (3)
C6—C10	1.369 (3)	C7—H5	0.89 (2)
C6—C7	1.379 (3)	C8—H6	0.94 (3)
C6—C5	1.457 (3)	C9—H4	0.90 (3)
C1—C3i	1.371 (3)
C4—O1—C5	102.87 (14)	C2—C1—H1	118.9 (13)
C4—N1—N2	106.44 (15)	C1i—C3—C2	119.80 (18)
C5—N2—N1	105.93 (16)	C1i—C3—H2	120.2 (12)
C3—C2—C1	119.71 (18)	C2—C3—H2	120.0 (12)
C3—C2—C4	120.80 (17)	C9—N3—C8	116.0 (2)
C1—C2—C4	119.48 (18)	C6—C10—C9	118.9 (2)
C10—C6—C7	117.7 (2)	C6—C10—H3	120.6 (14)
C10—C6—C5	120.01 (18)	C9—C10—H3	120.5 (14)
C7—C6—C5	122.2 (2)	C8—C7—C6	119.0 (2)
N1—C4—O1	112.27 (16)	C8—C7—H5	118.8 (15)
N1—C4—C2	128.76 (17)	C6—C7—H5	122.3 (15)
O1—C4—C2	118.96 (16)	N3—C8—C7	124.1 (2)
N2—C5—O1	112.49 (16)	N3—C8—H6	115.6 (16)
N2—C5—C6	128.40 (18)	C7—C8—H6	120.3 (16)
O1—C5—C6	119.09 (17)	N3—C9—C10	124.4 (2)
C3i—C1—C2	120.48 (19)	N3—C9—H4	117.0 (17)
C3i—C1—H1	120.5 (12)	C10—C9—H4	118.5 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H2···N3ii	0.94 (2)	2.52 (2)	3.407 (3)	158.7 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H2⋯N3i	0.94 (2)	2.52 (2)	3.407 (3)	158.7 (16)

Symmetry code: (i) .