5,5'-Bis(naphthalen-2-yl)-2,2'-bi(1,3,4-oxadiazole).

The title mol-ecule, C(24)H(14)N(4)O(2), lies on an inversion centre and the asymmetric unit containg one half-mol-ecule. The naphthalene ring systems are twisted slightly with respect to the oxadiazole rings, making a dihedral angle of 1.36 (6)°. These mol-ecules are π-stacked along the crystallographic a axis, with an inter-planar distance of 3.337 (1) Å. Adjacent mol-ecules are slipped from the 'ideal' cofacial π-stack in both the long and short mol-ecular axis (the long mol-ecular axis is defined as the line through the naphthalene C atom in the 6-position and the mol-ecular center, the short mol-ecular axis is in the mol-ecular plane perpendicular to it). The slip distance along the long mol-ecular axis (S(1)) is 7.064 (1) Å, nearly a two-ring-length displacement. The side slip (S(2), along the short mol-ecular axis) is 1.159 (8) Å.

Related literature

For the synthesis of 1,3,4-oxadiazole derivatives: see Schulz et al. (1997 ▶). For related structures: see Schulz et al. (2005 ▶); Qu et al. (2008 ▶); Landis et al. (2008 ▶).

Experimental

Crystal data

C24H14N4O2

M = 390.39

Monoclinic,

a = 7.8982 (16) Å

b = 5.7107 (11) Å

c = 21.503 (5) Å

β = 109.82 (3)°

V = 912.4 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.18 × 0.14 × 0.12 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.983, T max = 0.989

8518 measured reflections

2091 independent reflections

1468 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.106

S = 1.07

2091 reflections

136 parameters

H-atom parameters constrained

Δρmax = 0.16 e Å−3

Δρmin = −0.18 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶) and CrystalStructure (Rigaku/MSC, 2002 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811048513/vm2137sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811048513/vm2137Isup2.hkl

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

C24H14N4O2	Z = 2
Mr = 390.39	F(000) = 404
Monoclinic, P21/c	Dx = 1.421 Mg m−3
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 7.8982 (16) Å	µ = 0.09 mm−1
b = 5.7107 (11) Å	T = 293 K
c = 21.503 (5) Å	Block, colourless
β = 109.82 (3)°	0.18 × 0.14 × 0.12 mm
V = 912.4 (3) Å3

Rigaku R-AXIS RAPID diffractometer	2091 independent reflections
Radiation source: fine-focus sealed tube	1468 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scans	θmax = 27.5°, θmin = 3.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.983, Tmax = 0.989	k = −7→7
8518 measured reflections	l = −27→27

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.106	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0577P)2] where P = (Fo2 + 2Fc2)/3
2091 reflections	(Δ/σ)max = 0.001
136 parameters	Δρmax = 0.16 e Å−3
0 restraints	Δρmin = −0.18 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	0.18040 (11)	0.40921 (16)	0.97102 (4)	0.0412 (2)
N1	0.01904 (14)	0.7350 (2)	0.94532 (6)	0.0482 (3)
N2	0.14392 (14)	0.7347 (2)	0.91193 (6)	0.0479 (3)
C1	0.04644 (15)	0.5425 (2)	0.97855 (6)	0.0407 (3)
C2	0.23461 (16)	0.5413 (2)	0.92839 (6)	0.0388 (3)
C3	0.38061 (15)	0.4564 (2)	0.90721 (6)	0.0373 (3)
C4	0.46713 (17)	0.2407 (2)	0.93102 (6)	0.0448 (3)
H4	0.4287	0.1499	0.9596	0.054*
C5	0.60641 (17)	0.1660 (2)	0.91221 (7)	0.0453 (3)
H5	0.6637	0.0256	0.9288	0.054*
C6	0.66520 (15)	0.2993 (2)	0.86777 (6)	0.0389 (3)
C7	0.80712 (17)	0.2254 (3)	0.84590 (7)	0.0506 (4)
H7	0.8681	0.0868	0.8621	0.061*
C8	0.85466 (18)	0.3556 (3)	0.80150 (8)	0.0586 (4)
H8	0.9466	0.3037	0.7870	0.070*
C9	0.76681 (19)	0.5674 (3)	0.77722 (8)	0.0565 (4)
H9	0.8008	0.6543	0.7468	0.068*
C10	0.63230 (17)	0.6463 (3)	0.79789 (6)	0.0459 (3)
H10	0.5763	0.7881	0.7821	0.055*
C11	0.57699 (15)	0.5144 (2)	0.84322 (6)	0.0364 (3)
C12	0.43475 (15)	0.5888 (2)	0.86414 (6)	0.0379 (3)
H12	0.3768	0.7297	0.8485	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0390 (4)	0.0454 (6)	0.0423 (5)	0.0017 (4)	0.0180 (4)	0.0038 (4)
N1	0.0447 (6)	0.0538 (7)	0.0506 (6)	0.0060 (5)	0.0222 (5)	0.0051 (6)
N2	0.0464 (6)	0.0498 (7)	0.0518 (6)	0.0059 (5)	0.0225 (5)	0.0066 (5)
C1	0.0343 (6)	0.0481 (8)	0.0402 (6)	0.0009 (5)	0.0133 (5)	−0.0021 (6)
C2	0.0392 (6)	0.0417 (7)	0.0358 (6)	−0.0030 (5)	0.0131 (5)	0.0017 (5)
C3	0.0363 (6)	0.0379 (7)	0.0371 (6)	−0.0013 (5)	0.0115 (5)	−0.0009 (5)
C4	0.0512 (7)	0.0399 (7)	0.0453 (7)	0.0005 (6)	0.0190 (6)	0.0083 (6)
C5	0.0481 (7)	0.0357 (7)	0.0495 (7)	0.0050 (5)	0.0130 (6)	0.0036 (6)
C6	0.0366 (6)	0.0377 (7)	0.0403 (6)	0.0001 (5)	0.0103 (5)	−0.0054 (5)
C7	0.0433 (7)	0.0485 (9)	0.0588 (8)	0.0042 (6)	0.0156 (6)	−0.0084 (7)
C8	0.0438 (7)	0.0718 (11)	0.0680 (9)	−0.0010 (7)	0.0290 (7)	−0.0128 (8)
C9	0.0522 (8)	0.0680 (11)	0.0569 (8)	−0.0083 (7)	0.0285 (7)	0.0018 (8)
C10	0.0450 (7)	0.0465 (8)	0.0472 (7)	−0.0033 (6)	0.0168 (6)	0.0036 (6)
C11	0.0363 (6)	0.0366 (7)	0.0355 (6)	−0.0036 (5)	0.0110 (5)	−0.0029 (5)
C12	0.0395 (6)	0.0340 (7)	0.0391 (6)	0.0019 (5)	0.0118 (5)	0.0026 (5)

O1—C1	1.3568 (15)	C6—C7	1.4190 (17)
O1—C2	1.3636 (15)	C6—C11	1.4228 (18)
N1—C1	1.2889 (18)	C7—C8	1.360 (2)
N1—N2	1.4031 (16)	C7—H7	0.9300
N2—C2	1.2986 (17)	C8—C9	1.404 (2)
C1—C1i	1.443 (3)	C8—H8	0.9300
C2—C3	1.4588 (17)	C9—C10	1.3600 (19)
C3—C12	1.3714 (17)	C9—H9	0.9300
C3—C4	1.4175 (18)	C10—C11	1.4130 (18)
C4—C5	1.3629 (19)	C10—H10	0.9300
C4—H4	0.9300	C11—C12	1.4098 (17)
C5—C6	1.4173 (19)	C12—H12	0.9300
C5—H5	0.9300
C1—O1—C2	101.84 (10)	C7—C6—C11	118.45 (12)
C1—N1—N2	105.54 (11)	C8—C7—C6	120.48 (14)
C2—N2—N1	106.25 (11)	C8—C7—H7	119.8
N1—C1—O1	113.78 (11)	C6—C7—H7	119.8
N1—C1—C1i	127.93 (15)	C7—C8—C9	120.87 (14)
O1—C1—C1i	118.28 (15)	C7—C8—H8	119.6
N2—C2—O1	112.58 (11)	C9—C8—H8	119.6
N2—C2—C3	128.24 (12)	C10—C9—C8	120.39 (14)
O1—C2—C3	119.18 (12)	C10—C9—H9	119.8
C12—C3—C4	120.03 (11)	C8—C9—H9	119.8
C12—C3—C2	119.22 (12)	C9—C10—C11	120.50 (14)
C4—C3—C2	120.75 (12)	C9—C10—H10	119.8
C5—C4—C3	120.24 (12)	C11—C10—H10	119.8
C5—C4—H4	119.9	C12—C11—C10	121.71 (12)
C3—C4—H4	119.9	C12—C11—C6	119.00 (11)
C4—C5—C6	120.93 (13)	C10—C11—C6	119.29 (11)
C4—C5—H5	119.5	C3—C12—C11	120.93 (12)
C6—C5—H5	119.5	C3—C12—H12	119.5
C5—C6—C7	122.68 (13)	C11—C12—H12	119.5
C5—C6—C11	118.86 (11)
C1—N1—N2—C2	0.01 (14)	C4—C5—C6—C11	0.41 (19)
N2—N1—C1—O1	0.15 (15)	C5—C6—C7—C8	177.78 (13)
N2—N1—C1—C1i	179.92 (16)	C11—C6—C7—C8	−1.28 (19)
C2—O1—C1—N1	−0.23 (14)	C6—C7—C8—C9	1.1 (2)
C2—O1—C1—C1i	179.97 (14)	C7—C8—C9—C10	0.1 (2)
N1—N2—C2—O1	−0.16 (14)	C8—C9—C10—C11	−1.1 (2)
N1—N2—C2—C3	−179.98 (12)	C9—C10—C11—C12	−178.28 (12)
C1—O1—C2—N2	0.24 (13)	C9—C10—C11—C6	0.84 (19)
C1—O1—C2—C3	−179.92 (11)	C5—C6—C11—C12	0.36 (17)
N2—C2—C3—C12	−0.4 (2)	C7—C6—C11—C12	179.46 (11)
O1—C2—C3—C12	179.76 (10)	C5—C6—C11—C10	−178.78 (11)
N2—C2—C3—C4	179.09 (12)	C7—C6—C11—C10	0.33 (17)
O1—C2—C3—C4	−0.72 (18)	C4—C3—C12—C11	−0.42 (18)
C12—C3—C4—C5	1.19 (19)	C2—C3—C12—C11	179.11 (11)
C2—C3—C4—C5	−178.33 (12)	C10—C11—C12—C3	178.77 (11)
C3—C4—C5—C6	−1.2 (2)	C6—C11—C12—C3	−0.35 (18)
C4—C5—C6—C7	−178.66 (12)