2,5-Bis(4-meth-oxy-phen-yl)-1,3,4-oxadiazole.

In the title compound, C(16)H(14)N(2)O(3), the essentially planar 1,3,4-oxadiazole ring [maximum deviation = 0.0021 (11) Å] is inclined at dihedral angles of 8.06 (6) and 11.21 (6)° with respect to the two benzene rings; the dihedral angle between the latter rings is 11.66 (5)°. In the crystal, short inter-molecular C⋯O inter-actions [2.9968 (15) Å] connect adjacent mol-ecules into chains propagating in [203]. The crystal structure is further stabilized by weak inter-molecular C-H⋯π inter-actions.

Related literature

For general background to and applications of the title compound, see: Andersen et al. (1994 ▶); Clitherow et al. (1996 ▶); Hegde et al. (2008 ▶); Rai et al. (2008 ▶); Showell et al. (1991 ▶). For closely related 2,5-diphenyl-1,3,4-oxadiazole structures, see: Reck et al. (2003a ▶,b ▶); Franco et al. (2003 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C16H14N2O3

M = 282.29

Monoclinic,

a = 10.7525 (2) Å

b = 11.8973 (2) Å

c = 11.6340 (2) Å

β = 115.434 (1)°

V = 1344.04 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.53 × 0.49 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.950, T max = 0.992

17061 measured reflections

4744 independent reflections

3744 reflections with I > 2σ(I)

R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.137

S = 1.03

4744 reflections

246 parameters

All H-atom parameters refined

Δρmax = 0.38 e Å−3

Δρmin = −0.30 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810044405/hb5714sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810044405/hb5714Isup2.hkl

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

C16H14N2O3	F(000) = 592
Mr = 282.29	Dx = 1.395 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5014 reflections
a = 10.7525 (2) Å	θ = 2.6–32.2°
b = 11.8973 (2) Å	µ = 0.10 mm−1
c = 11.6340 (2) Å	T = 100 K
β = 115.434 (1)°	Block, yellow
V = 1344.04 (4) Å3	0.53 × 0.49 × 0.09 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	4744 independent reflections
Radiation source: fine-focus sealed tube	3744 reflections with I > 2σ(I)
graphite	Rint = 0.027
φ and ω scans	θmax = 32.3°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −16→15
Tmin = 0.950, Tmax = 0.992	k = −17→17
17061 measured reflections	l = −14→17

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	All H-atom parameters refined
S = 1.03	w = 1/[σ2(Fo2) + (0.079P)2 + 0.1649P] where P = (Fo2 + 2Fc2)/3
4744 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.89032 (6)	0.25303 (6)	0.21170 (6)	0.01974 (15)
O2	0.49848 (8)	0.12006 (7)	−0.35883 (8)	0.0333 (2)
O3	1.26608 (8)	0.16634 (6)	0.80451 (7)	0.02542 (17)
N1	0.84586 (9)	0.42831 (7)	0.14199 (9)	0.02542 (19)
N2	0.93713 (9)	0.43051 (7)	0.27255 (8)	0.02513 (19)
C1	0.64742 (10)	0.33907 (9)	−0.11316 (10)	0.0243 (2)
C2	0.56651 (10)	0.29145 (9)	−0.23102 (10)	0.0257 (2)
C3	0.57391 (10)	0.17639 (9)	−0.24904 (10)	0.0247 (2)
C4	0.66395 (10)	0.10958 (9)	−0.14829 (10)	0.0264 (2)
C5	0.74483 (10)	0.15763 (8)	−0.03171 (10)	0.0234 (2)
C6	0.73715 (9)	0.27300 (8)	−0.01231 (9)	0.02039 (18)
C7	0.82192 (9)	0.32333 (8)	0.11073 (9)	0.02031 (18)
C8	0.95953 (9)	0.32608 (7)	0.30883 (9)	0.01932 (18)
C9	1.04150 (9)	0.28123 (7)	0.43534 (9)	0.01863 (17)
C10	1.06169 (9)	0.16598 (8)	0.45607 (9)	0.01989 (18)
C11	1.13636 (9)	0.12351 (8)	0.57833 (9)	0.02060 (18)
C12	1.19097 (9)	0.19768 (8)	0.68094 (9)	0.01974 (18)
C13	1.17027 (10)	0.31372 (8)	0.66105 (10)	0.0232 (2)
C14	1.09745 (10)	0.35469 (8)	0.53959 (10)	0.02276 (19)
C15	0.42071 (11)	0.18563 (12)	−0.47047 (11)	0.0320 (2)
C16	1.29532 (13)	0.05018 (10)	0.82938 (11)	0.0312 (2)
H1A	0.6395 (13)	0.4157 (12)	−0.1004 (13)	0.031 (3)*
H2A	0.5040 (16)	0.3408 (13)	−0.2994 (15)	0.044 (4)*
H4A	0.6699 (14)	0.0323 (13)	−0.1637 (14)	0.034 (4)*
H5A	0.8051 (14)	0.1104 (12)	0.0334 (13)	0.033 (4)*
H10A	1.0288 (13)	0.1131 (11)	0.3879 (13)	0.028 (3)*
H11A	1.1508 (14)	0.0475 (12)	0.5874 (14)	0.033 (3)*
H13A	1.2011 (15)	0.3619 (13)	0.7306 (14)	0.039 (4)*
H14A	1.0822 (13)	0.4342 (12)	0.5266 (13)	0.031 (3)*
H15A	0.3446 (14)	0.2322 (11)	−0.4612 (13)	0.031 (3)*
H15B	0.4821 (14)	0.2357 (12)	−0.4910 (14)	0.030 (3)*
H15C	0.3802 (16)	0.1299 (14)	−0.5399 (15)	0.043 (4)*
H16A	1.2087 (16)	0.0060 (13)	0.8025 (15)	0.044 (4)*
H16B	1.3518 (15)	0.0229 (13)	0.7875 (14)	0.040 (4)*
H16C	1.3490 (16)	0.0457 (14)	0.9238 (16)	0.046 (4)*

	U11	U22	U33	U12	U13	U23
O1	0.0201 (3)	0.0161 (3)	0.0210 (3)	0.0006 (2)	0.0069 (2)	0.0022 (2)
O2	0.0298 (4)	0.0347 (4)	0.0238 (4)	−0.0009 (3)	0.0003 (3)	0.0011 (3)
O3	0.0325 (4)	0.0234 (4)	0.0183 (3)	0.0021 (3)	0.0089 (3)	0.0011 (3)
N1	0.0316 (4)	0.0193 (4)	0.0244 (4)	0.0024 (3)	0.0112 (3)	0.0035 (3)
N2	0.0324 (4)	0.0184 (4)	0.0236 (4)	0.0022 (3)	0.0111 (3)	0.0020 (3)
C1	0.0247 (4)	0.0219 (5)	0.0262 (5)	0.0025 (3)	0.0108 (4)	0.0062 (4)
C2	0.0220 (4)	0.0283 (5)	0.0246 (5)	0.0024 (3)	0.0080 (4)	0.0086 (4)
C3	0.0197 (4)	0.0282 (5)	0.0224 (4)	−0.0015 (3)	0.0054 (3)	0.0031 (4)
C4	0.0243 (4)	0.0222 (5)	0.0265 (5)	0.0002 (3)	0.0050 (4)	0.0023 (4)
C5	0.0210 (4)	0.0217 (4)	0.0237 (4)	0.0009 (3)	0.0058 (3)	0.0050 (3)
C6	0.0183 (4)	0.0213 (4)	0.0219 (4)	0.0005 (3)	0.0090 (3)	0.0045 (3)
C7	0.0204 (4)	0.0192 (4)	0.0223 (4)	0.0031 (3)	0.0101 (3)	0.0054 (3)
C8	0.0210 (4)	0.0165 (4)	0.0217 (4)	0.0007 (3)	0.0103 (3)	−0.0001 (3)
C9	0.0192 (4)	0.0161 (4)	0.0213 (4)	0.0001 (3)	0.0092 (3)	−0.0003 (3)
C10	0.0201 (4)	0.0161 (4)	0.0220 (4)	−0.0010 (3)	0.0076 (3)	−0.0020 (3)
C11	0.0222 (4)	0.0156 (4)	0.0228 (4)	−0.0009 (3)	0.0086 (3)	−0.0005 (3)
C12	0.0212 (4)	0.0206 (4)	0.0185 (4)	0.0006 (3)	0.0096 (3)	0.0004 (3)
C13	0.0284 (4)	0.0195 (4)	0.0223 (4)	0.0010 (3)	0.0113 (4)	−0.0039 (3)
C14	0.0275 (4)	0.0163 (4)	0.0246 (4)	0.0017 (3)	0.0112 (4)	−0.0015 (3)
C15	0.0237 (4)	0.0470 (7)	0.0213 (5)	0.0004 (4)	0.0059 (4)	0.0067 (4)
C16	0.0390 (6)	0.0239 (5)	0.0242 (5)	0.0018 (4)	0.0074 (4)	0.0053 (4)

O1—C8	1.3652 (11)	C6—C7	1.4552 (13)
O1—C7	1.3704 (11)	C8—C9	1.4537 (13)
O2—C3	1.3597 (13)	C9—C10	1.3930 (12)
O2—C15	1.4359 (13)	C9—C14	1.4036 (13)
O3—C12	1.3641 (11)	C10—C11	1.3937 (13)
O3—C16	1.4193 (13)	C10—H10A	0.954 (14)
N1—C7	1.2954 (13)	C11—C12	1.3952 (13)
N1—N2	1.4110 (12)	C11—H11A	0.916 (14)
N2—C8	1.3010 (12)	C12—C13	1.4017 (14)
C1—C2	1.3905 (15)	C13—C14	1.3774 (14)
C1—C6	1.3975 (13)	C13—H13A	0.929 (16)
C1—H1A	0.934 (14)	C14—H14A	0.960 (14)
C2—C3	1.3923 (15)	C15—H15A	1.031 (14)
C2—H2A	0.985 (16)	C15—H15B	0.992 (14)
C3—C4	1.4029 (14)	C15—H15C	0.990 (16)
C4—C5	1.3819 (14)	C16—H16A	0.996 (16)
C4—H4A	0.944 (15)	C16—H16B	0.982 (16)
C5—C6	1.3992 (14)	C16—H16C	0.999 (17)
C5—H5A	0.943 (14)
C8—O1—C7	102.83 (7)	C10—C9—C8	121.21 (8)
C3—O2—C15	117.56 (9)	C14—C9—C8	119.66 (8)
C12—O3—C16	117.39 (8)	C9—C10—C11	120.82 (8)
C7—N1—N2	106.41 (8)	C9—C10—H10A	122.1 (8)
C8—N2—N1	106.13 (8)	C11—C10—H10A	117.1 (8)
C2—C1—C6	120.85 (9)	C10—C11—C12	119.35 (9)
C2—C1—H1A	119.5 (9)	C10—C11—H11A	118.0 (9)
C6—C1—H1A	119.6 (9)	C12—C11—H11A	122.5 (9)
C1—C2—C3	119.80 (9)	O3—C12—C11	124.75 (9)
C1—C2—H2A	118.4 (9)	O3—C12—C13	115.05 (8)
C3—C2—H2A	121.8 (9)	C11—C12—C13	120.20 (9)
O2—C3—C2	125.20 (9)	C14—C13—C12	119.87 (9)
O2—C3—C4	115.14 (9)	C14—C13—H13A	120.6 (10)
C2—C3—C4	119.66 (9)	C12—C13—H13A	119.5 (10)
C5—C4—C3	120.21 (10)	C13—C14—C9	120.66 (9)
C5—C4—H4A	121.6 (9)	C13—C14—H14A	119.5 (8)
C3—C4—H4A	118.2 (9)	C9—C14—H14A	119.8 (8)
C4—C5—C6	120.55 (9)	O2—C15—H15A	112.1 (8)
C4—C5—H5A	117.9 (9)	O2—C15—H15B	110.8 (8)
C6—C5—H5A	121.6 (9)	H15A—C15—H15B	110.0 (11)
C1—C6—C5	118.92 (9)	O2—C15—H15C	104.8 (10)
C1—C6—C7	120.62 (9)	H15A—C15—H15C	110.8 (12)
C5—C6—C7	120.46 (8)	H15B—C15—H15C	108.1 (12)
N1—C7—O1	112.27 (9)	O3—C16—H16A	110.8 (9)
N1—C7—C6	129.63 (9)	O3—C16—H16B	110.5 (9)
O1—C7—C6	118.09 (8)	H16A—C16—H16B	111.3 (13)
N2—C8—O1	112.35 (8)	O3—C16—H16C	104.4 (10)
N2—C8—C9	128.77 (9)	H16A—C16—H16C	109.8 (13)
O1—C8—C9	118.84 (8)	H16B—C16—H16C	109.8 (13)
C10—C9—C14	119.09 (9)
C7—N1—N2—C8	−0.41 (11)	N1—N2—C8—O1	0.33 (11)
C6—C1—C2—C3	0.44 (16)	N1—N2—C8—C9	−177.28 (9)
C15—O2—C3—C2	9.99 (16)	C7—O1—C8—N2	−0.13 (10)
C15—O2—C3—C4	−170.60 (10)	C7—O1—C8—C9	177.74 (8)
C1—C2—C3—O2	178.82 (10)	N2—C8—C9—C10	−175.90 (10)
C1—C2—C3—C4	−0.55 (16)	O1—C8—C9—C10	6.62 (13)
O2—C3—C4—C5	−179.38 (10)	N2—C8—C9—C14	6.42 (16)
C2—C3—C4—C5	0.05 (16)	O1—C8—C9—C14	−171.05 (8)
C3—C4—C5—C6	0.57 (16)	C14—C9—C10—C11	−0.04 (14)
C2—C1—C6—C5	0.18 (15)	C8—C9—C10—C11	−177.72 (9)
C2—C1—C6—C7	179.80 (9)	C9—C10—C11—C12	0.20 (14)
C4—C5—C6—C1	−0.69 (15)	C16—O3—C12—C11	2.71 (14)
C4—C5—C6—C7	179.69 (9)	C16—O3—C12—C13	−177.29 (9)
N2—N1—C7—O1	0.35 (11)	C10—C11—C12—O3	−179.73 (8)
N2—N1—C7—C6	−178.82 (9)	C10—C11—C12—C13	0.27 (14)
C8—O1—C7—N1	−0.15 (10)	O3—C12—C13—C14	179.08 (9)
C8—O1—C7—C6	179.12 (8)	C11—C12—C13—C14	−0.92 (15)
C1—C6—C7—N1	−11.61 (16)	C12—C13—C14—C9	1.10 (15)
C5—C6—C7—N1	168.01 (10)	C10—C9—C14—C13	−0.62 (14)
C1—C6—C7—O1	169.27 (9)	C8—C9—C14—C13	177.10 (9)
C5—C6—C7—O1	−11.12 (13)

Cg1 and Cg2 are the centroids of C9–C14 and C1–C6 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15A···Cg1i	1.031 (14)	2.563 (16)	3.4903 (14)	149.4 (10)
C15—H15B···Cg2ii	0.992 (14)	2.994 (16)	3.8804 (14)	149.4 (11)

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of C9–C14 and C1–C6 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C15—H15A⋯Cg1i	1.031 (14)	2.563 (16)	3.4903 (14)	149.4 (10)
C15—H15B⋯Cg2ii	0.992 (14)	2.994 (16)	3.8804 (14)	149.4 (11)

Symmetry codes: (i) ; (ii) .