3-(2,4-Dichloro-phen-yl)-5-phenyl-1,2,4-oxadiazole.

In the title compound, C(14)H(8)Cl(2)N(2)O, the dihedral angles between the plane of the oxadiazole ring and those of the benzene rings are 2.3 (1) and 9.5 (1)°. In the crystal, mol-ecules are linked into chains along the c axis by C-H⋯Cl inter-actions. These chains are stacked along the a axis.

Related literature

For the biological properties of heterocyclic compounds including oxadiazo­les, see: Andersen et al. (1994 ▶); Showell et al. (1991 ▶); Watjen et al. (1989 ▶); Swain et al. (1991 ▶); Clitherow et al. (1996 ▶). For their pharmacological and medicinal activity, see: Isloor et al. (2010 ▶); Chandrakantha et al. (2010 ▶). For a related structure, see: Wang et al. (2006 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H8Cl2N2O

M = 291.12

Triclinic,

a = 3.8035 (2) Å

b = 10.9666 (7) Å

c = 14.6949 (9) Å

α = 99.044 (2)°

β = 91.158 (2)°

γ = 98.891 (2)°

V = 597.43 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.53 mm−1

T = 100 K

0.41 × 0.13 × 0.09 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.809, T max = 0.953

12084 measured reflections

2692 independent reflections

2355 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.121

S = 1.14

2692 reflections

204 parameters

All H-atom parameters refined

Δρmax = 0.55 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S160053681000927X/sj2743sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681000927X/sj2743Isup2.hkl

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

C14H8Cl2N2O	Z = 2
Mr = 291.12	F(000) = 296
Triclinic, P1	Dx = 1.618 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 3.8035 (2) Å	Cell parameters from 7625 reflections
b = 10.9666 (7) Å	θ = 2.5–36.0°
c = 14.6949 (9) Å	µ = 0.53 mm−1
α = 99.044 (2)°	T = 100 K
β = 91.158 (2)°	Block, colourless
γ = 98.891 (2)°	0.41 × 0.13 × 0.09 mm
V = 597.43 (6) Å3

Bruker SMART APEXII CCD area-detector diffractometer	2692 independent reflections
Radiation source: fine-focus sealed tube	2355 reflections with I > 2σ(I)
graphite	Rint = 0.035
φ and ω scans	θmax = 27.5°, θmin = 1.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −4→4
Tmin = 0.809, Tmax = 0.953	k = −14→14
12084 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121	All H-atom parameters refined
S = 1.14	w = 1/[σ2(Fo2) + (0.0727P)2 + 0.3227P] where P = (Fo2 + 2Fc2)/3
2692 reflections	(Δ/σ)max = 0.001
204 parameters	Δρmax = 0.55 e Å−3
0 restraints	Δρmin = −0.39 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems 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
Cl1	0.67894 (14)	0.17290 (4)	0.56305 (3)	0.02303 (17)
Cl2	0.74585 (13)	0.52050 (4)	0.34575 (3)	0.01905 (16)
O1	1.0808 (4)	0.40239 (12)	0.07273 (9)	0.0188 (3)
N1	1.1293 (4)	0.22993 (14)	0.12866 (10)	0.0152 (3)
N2	0.9704 (5)	0.42193 (15)	0.16440 (11)	0.0186 (3)
C1	1.3840 (5)	0.31992 (18)	−0.09742 (13)	0.0182 (4)
C2	1.5167 (6)	0.27272 (19)	−0.18064 (13)	0.0207 (4)
C3	1.5623 (5)	0.14861 (19)	−0.19917 (13)	0.0197 (4)
C4	1.4763 (5)	0.06975 (18)	−0.13435 (12)	0.0180 (4)
C5	1.3476 (5)	0.11647 (17)	−0.05099 (12)	0.0157 (4)
C6	1.3013 (5)	0.24188 (17)	−0.03204 (12)	0.0146 (4)
C7	1.1707 (5)	0.28734 (17)	0.05746 (12)	0.0152 (4)
C8	1.0052 (5)	0.31698 (17)	0.19311 (12)	0.0141 (4)
C9	0.9255 (5)	0.28872 (16)	0.28577 (12)	0.0146 (4)
C10	0.9670 (5)	0.16979 (17)	0.30360 (12)	0.0155 (4)
C11	0.8962 (5)	0.13252 (18)	0.38802 (13)	0.0172 (4)
C12	0.7795 (5)	0.21663 (18)	0.45703 (12)	0.0171 (4)
C13	0.7382 (5)	0.33600 (18)	0.44337 (12)	0.0172 (4)
C14	0.8094 (5)	0.37087 (16)	0.35794 (12)	0.0155 (4)
H1A	1.360 (7)	0.402 (3)	−0.0859 (17)	0.026 (6)*
H2A	1.572 (7)	0.323 (2)	−0.2233 (18)	0.024 (6)*
H3A	1.664 (7)	0.121 (2)	−0.2558 (18)	0.029 (7)*
H4A	1.483 (6)	−0.015 (2)	−0.1458 (15)	0.015 (5)*
H5A	1.325 (7)	0.068 (2)	−0.0091 (17)	0.020 (6)*
H10A	1.028 (7)	0.109 (2)	0.2564 (16)	0.019 (6)*
H11A	0.922 (6)	0.054 (2)	0.3967 (15)	0.014 (5)*
H13A	0.635 (7)	0.390 (2)	0.4924 (17)	0.022 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0276 (3)	0.0272 (3)	0.0163 (2)	0.0063 (2)	0.00286 (18)	0.00754 (18)
Cl2	0.0228 (3)	0.0169 (2)	0.0191 (2)	0.00957 (18)	−0.00111 (17)	0.00205 (17)
O1	0.0261 (8)	0.0160 (6)	0.0165 (6)	0.0086 (5)	0.0003 (5)	0.0045 (5)
N1	0.0149 (8)	0.0165 (7)	0.0148 (7)	0.0051 (6)	−0.0008 (6)	0.0025 (6)
N2	0.0233 (9)	0.0185 (8)	0.0160 (7)	0.0077 (6)	0.0014 (6)	0.0043 (6)
C1	0.0180 (10)	0.0182 (9)	0.0199 (9)	0.0044 (7)	−0.0031 (7)	0.0068 (7)
C2	0.0208 (10)	0.0256 (10)	0.0180 (9)	0.0034 (8)	−0.0013 (7)	0.0112 (7)
C3	0.0185 (10)	0.0277 (10)	0.0139 (8)	0.0062 (8)	−0.0005 (7)	0.0039 (7)
C4	0.0174 (10)	0.0194 (9)	0.0178 (8)	0.0050 (7)	−0.0031 (7)	0.0035 (7)
C5	0.0138 (9)	0.0173 (8)	0.0171 (8)	0.0031 (7)	−0.0019 (6)	0.0063 (7)
C6	0.0121 (9)	0.0171 (8)	0.0148 (8)	0.0026 (7)	−0.0031 (6)	0.0037 (6)
C7	0.0128 (9)	0.0153 (8)	0.0181 (8)	0.0037 (7)	−0.0037 (6)	0.0036 (6)
C8	0.0106 (9)	0.0157 (8)	0.0160 (8)	0.0035 (6)	−0.0028 (6)	0.0016 (6)
C9	0.0103 (9)	0.0176 (9)	0.0157 (8)	0.0023 (7)	−0.0034 (6)	0.0026 (6)
C10	0.0137 (9)	0.0166 (8)	0.0163 (8)	0.0040 (7)	−0.0016 (6)	0.0013 (6)
C11	0.0170 (10)	0.0163 (9)	0.0191 (8)	0.0032 (7)	−0.0021 (7)	0.0050 (7)
C12	0.0146 (9)	0.0222 (9)	0.0150 (8)	0.0027 (7)	−0.0016 (6)	0.0049 (7)
C13	0.0150 (9)	0.0203 (9)	0.0164 (8)	0.0050 (7)	−0.0024 (7)	0.0009 (7)
C14	0.0128 (9)	0.0157 (8)	0.0183 (8)	0.0036 (7)	−0.0029 (6)	0.0026 (7)

Cl1—C12	1.7338 (18)	C4—H4A	0.92 (2)
Cl2—C14	1.7310 (18)	C5—C6	1.399 (3)
O1—C7	1.344 (2)	C5—H5A	0.87 (2)
O1—N2	1.413 (2)	C6—C7	1.457 (2)
N1—C7	1.303 (2)	C8—C9	1.470 (2)
N1—C8	1.380 (2)	C9—C10	1.401 (3)
N2—C8	1.311 (2)	C9—C14	1.405 (3)
C1—C2	1.387 (3)	C10—C11	1.385 (3)
C1—C6	1.394 (2)	C10—H10A	0.94 (2)
C1—H1A	0.91 (3)	C11—C12	1.388 (3)
C2—C3	1.384 (3)	C11—H11A	0.91 (2)
C2—H2A	0.91 (3)	C12—C13	1.387 (3)
C3—C4	1.395 (3)	C13—C14	1.389 (3)
C3—H3A	0.95 (3)	C13—H13A	0.99 (3)
C4—C5	1.381 (3)
C7—O1—N2	106.71 (14)	O1—C7—C6	119.03 (16)
C7—N1—C8	102.57 (15)	N2—C8—N1	114.69 (16)
C8—N2—O1	103.00 (15)	N2—C8—C9	125.14 (17)
C2—C1—C6	119.53 (18)	N1—C8—C9	120.17 (15)
C2—C1—H1A	119.2 (16)	C10—C9—C14	117.16 (16)
C6—C1—H1A	121.2 (16)	C10—C9—C8	117.41 (16)
C3—C2—C1	120.30 (17)	C14—C9—C8	125.43 (16)
C3—C2—H2A	119.8 (16)	C11—C10—C9	122.41 (17)
C1—C2—H2A	119.9 (16)	C11—C10—H10A	116.9 (14)
C2—C3—C4	120.40 (18)	C9—C10—H10A	120.5 (14)
C2—C3—H3A	117.6 (16)	C10—C11—C12	118.35 (17)
C4—C3—H3A	122.0 (16)	C10—C11—H11A	120.0 (14)
C5—C4—C3	119.60 (18)	C12—C11—H11A	121.6 (14)
C5—C4—H4A	116.9 (14)	C13—C12—C11	121.57 (17)
C3—C4—H4A	123.3 (14)	C13—C12—Cl1	118.49 (15)
C4—C5—C6	120.14 (17)	C11—C12—Cl1	119.94 (15)
C4—C5—H5A	117.2 (16)	C12—C13—C14	118.95 (17)
C6—C5—H5A	122.2 (16)	C12—C13—H13A	118.8 (14)
C1—C6—C5	120.04 (17)	C14—C13—H13A	121.9 (14)
C1—C6—C7	121.86 (17)	C13—C14—C9	121.56 (17)
C5—C6—C7	118.10 (16)	C13—C14—Cl2	116.22 (14)
N1—C7—O1	113.04 (16)	C9—C14—Cl2	122.21 (14)
N1—C7—C6	127.93 (16)
C7—O1—N2—C8	−0.24 (19)	C7—N1—C8—N2	0.1 (2)
C6—C1—C2—C3	0.8 (3)	C7—N1—C8—C9	−179.53 (16)
C1—C2—C3—C4	−0.2 (3)	N2—C8—C9—C10	177.93 (18)
C2—C3—C4—C5	−0.5 (3)	N1—C8—C9—C10	−2.5 (3)
C3—C4—C5—C6	0.5 (3)	N2—C8—C9—C14	−1.8 (3)
C2—C1—C6—C5	−0.9 (3)	N1—C8—C9—C14	177.79 (17)
C2—C1—C6—C7	178.25 (17)	C14—C9—C10—C11	0.4 (3)
C4—C5—C6—C1	0.2 (3)	C8—C9—C10—C11	−179.33 (17)
C4—C5—C6—C7	−178.94 (17)	C9—C10—C11—C12	0.1 (3)
C8—N1—C7—O1	−0.2 (2)	C10—C11—C12—C13	−0.9 (3)
C8—N1—C7—C6	179.12 (18)	C10—C11—C12—Cl1	178.69 (14)
N2—O1—C7—N1	0.3 (2)	C11—C12—C13—C14	1.2 (3)
N2—O1—C7—C6	−179.11 (15)	Cl1—C12—C13—C14	−178.38 (14)
C1—C6—C7—N1	−169.98 (19)	C12—C13—C14—C9	−0.7 (3)
C5—C6—C7—N1	9.1 (3)	C12—C13—C14—Cl2	179.14 (14)
C1—C6—C7—O1	9.4 (3)	C10—C9—C14—C13	−0.1 (3)
C5—C6—C7—O1	−171.53 (16)	C8—C9—C14—C13	179.63 (17)
O1—N2—C8—N1	0.1 (2)	C10—C9—C14—Cl2	−179.90 (14)
O1—N2—C8—C9	179.68 (16)	C8—C9—C14—Cl2	−0.2 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···Cl1i	0.95 (3)	2.81 (3)	3.577 (2)	138.6 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯Cl1i	0.95 (3)	2.81 (3)	3.577 (2)	138.6 (19)

Symmetry code: (i) .