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

In the title compound, C(14)H(7)Cl(2)N(3)O(3), the dichloro-phenyl and nitro-phenyl rings form dihedral angles of 5.4 (2) and 4.0 (2)°, respectively, with the oxadiazole ring. The nitro group is twisted out of the attached benzene ring by a dihedral angle of 10.4 (3)°. In the crystal, mol-ecules are linked into a chain along the a axis by C-H⋯N hydrogen bonds.

Related literature

For the biological activity 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 ▶); Isloor et al. (2010 ▶); Chandrakantha et al. (2010 ▶). For related structures, see: Wang et al. (2006 ▶); Fun et al. (2010a ▶,b ▶).

Experimental

Crystal data

C14H7Cl2N3O3

M = 336.13

Orthorhombic,

a = 13.5272 (5) Å

b = 6.5362 (2) Å

c = 15.6880 (5) Å

V = 1387.08 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.48 mm−1

T = 296 K

0.37 × 0.11 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.843, T max = 0.980

9845 measured reflections

2658 independent reflections

2029 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.091

S = 1.06

2658 reflections

199 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.22 e Å−3

Absolute structure: Flack (1983 ▶), 1243 Friedel pairs

Flack parameter: −0.01 (7)

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/S1600536810011153/ci5063sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011153/ci5063Isup2.hkl

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

C14H7Cl2N3O3	F(000) = 680
Mr = 336.13	Dx = 1.610 Mg m−3
Orthorhombic, Pca21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2ac	Cell parameters from 2389 reflections
a = 13.5272 (5) Å	θ = 2.6–30.1°
b = 6.5362 (2) Å	µ = 0.48 mm−1
c = 15.6880 (5) Å	T = 296 K
V = 1387.08 (8) Å3	Plate, colourless
Z = 4	0.37 × 0.11 × 0.04 mm

Bruker SMART APEXII CCD area-detector diffractometer	2658 independent reflections
Radiation source: fine-focus sealed tube	2029 reflections with I > 2σ(I)
graphite	Rint = 0.045
φ and ω scans	θmax = 26.0°, θmin = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −13→16
Tmin = 0.843, Tmax = 0.980	k = −7→8
9845 measured reflections	l = −17→19

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.048	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0361P)2 + 0.1623P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.001
2658 reflections	Δρmax = 0.24 e Å−3
199 parameters	Δρmin = −0.22 e Å−3
1 restraint	Absolute structure: Flack (1983), 1243 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.01 (7)

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	0.37074 (7)	1.17134 (15)	0.20371 (7)	0.0672 (3)
Cl2	0.08039 (7)	0.73697 (16)	0.34239 (10)	0.0814 (4)
O1	0.15793 (17)	0.3687 (4)	0.41360 (18)	0.0643 (8)
O2	0.3673 (2)	−0.6615 (5)	0.6679 (2)	0.0975 (12)
O3	0.5067 (2)	−0.5915 (5)	0.6109 (2)	0.0959 (11)
N1	0.1636 (2)	0.1879 (5)	0.4615 (2)	0.0653 (10)
N2	0.3154 (2)	0.2966 (4)	0.4278 (2)	0.0454 (7)
N3	0.4200 (3)	−0.5541 (5)	0.6249 (2)	0.0646 (9)
C1	0.3731 (2)	0.6429 (5)	0.3289 (2)	0.0515 (10)
H1A	0.4198	0.5472	0.3463	0.062*
C2	0.4043 (3)	0.8143 (5)	0.2848 (3)	0.0562 (10)
H2A	0.4709	0.8346	0.2729	0.067*
C3	0.3342 (3)	0.9546 (5)	0.2589 (2)	0.0478 (9)
C4	0.2351 (3)	0.9269 (5)	0.2767 (2)	0.0493 (9)
H4A	0.1888	1.0233	0.2594	0.059*
C5	0.2060 (2)	0.7551 (5)	0.3204 (2)	0.0484 (9)
C6	0.2735 (2)	0.6087 (4)	0.3481 (2)	0.0417 (8)
C7	0.2522 (2)	0.4235 (5)	0.3964 (2)	0.0423 (8)
C8	0.2581 (3)	0.1536 (5)	0.4676 (2)	0.0434 (8)
C9	0.2984 (2)	−0.0278 (5)	0.5105 (2)	0.0411 (8)
C10	0.2372 (2)	−0.1701 (5)	0.5499 (2)	0.0463 (9)
H10A	0.1692	−0.1493	0.5501	0.056*
C11	0.2759 (3)	−0.3416 (5)	0.5887 (2)	0.0491 (10)
H11A	0.2350	−0.4357	0.6158	0.059*
C12	0.3767 (3)	−0.3693 (5)	0.5861 (2)	0.0457 (9)
C13	0.4388 (3)	−0.2323 (5)	0.5472 (2)	0.0547 (10)
H13A	0.5066	−0.2559	0.5458	0.066*
C14	0.3995 (2)	−0.0590 (5)	0.5103 (2)	0.0508 (9)
H14A	0.4411	0.0369	0.4851	0.061*

	U11	U22	U33	U12	U13	U23
Cl1	0.0778 (7)	0.0595 (6)	0.0642 (6)	−0.0179 (5)	0.0002 (6)	0.0100 (6)
Cl2	0.0403 (4)	0.0675 (6)	0.1363 (11)	−0.0026 (5)	−0.0083 (7)	0.0236 (7)
O1	0.0468 (14)	0.0596 (15)	0.086 (2)	0.0041 (12)	0.0112 (14)	0.0228 (15)
O2	0.089 (2)	0.0758 (19)	0.127 (3)	0.0000 (18)	0.006 (2)	0.045 (2)
O3	0.070 (2)	0.094 (2)	0.124 (3)	0.0193 (18)	−0.001 (2)	0.035 (2)
N1	0.0445 (17)	0.0621 (19)	0.089 (3)	0.0045 (15)	0.0144 (19)	0.0230 (19)
N2	0.0442 (16)	0.0428 (15)	0.0493 (18)	−0.0004 (14)	0.0019 (15)	−0.0026 (15)
N3	0.066 (2)	0.061 (2)	0.066 (2)	0.0007 (19)	−0.007 (2)	0.0065 (19)
C1	0.046 (2)	0.0437 (19)	0.065 (3)	0.0046 (14)	0.0124 (19)	−0.0034 (18)
C2	0.051 (2)	0.054 (2)	0.065 (3)	−0.0046 (18)	0.015 (2)	−0.009 (2)
C3	0.061 (2)	0.044 (2)	0.038 (2)	−0.0077 (17)	0.0005 (18)	−0.0042 (17)
C4	0.050 (2)	0.0450 (19)	0.053 (2)	0.0004 (16)	−0.0104 (18)	0.0052 (18)
C5	0.0418 (18)	0.0520 (19)	0.052 (2)	−0.0054 (16)	−0.0026 (17)	−0.0072 (19)
C6	0.0440 (18)	0.0357 (15)	0.046 (2)	0.0000 (13)	0.0014 (17)	−0.0082 (18)
C7	0.0402 (18)	0.0428 (17)	0.044 (2)	−0.0013 (16)	0.0029 (17)	−0.0085 (17)
C8	0.0472 (19)	0.0424 (17)	0.040 (2)	−0.0011 (17)	0.0037 (19)	−0.0072 (16)
C9	0.0462 (19)	0.0400 (17)	0.0370 (19)	0.0007 (15)	0.0012 (17)	−0.0081 (16)
C10	0.0367 (18)	0.052 (2)	0.050 (2)	0.0023 (16)	0.0099 (17)	−0.0048 (18)
C11	0.054 (2)	0.0464 (19)	0.047 (2)	−0.0071 (16)	0.0106 (19)	0.0000 (18)
C12	0.050 (2)	0.0432 (19)	0.043 (2)	−0.0008 (16)	−0.0008 (17)	0.0002 (17)
C13	0.045 (2)	0.059 (2)	0.060 (3)	−0.0018 (18)	−0.0032 (19)	0.006 (2)
C14	0.044 (2)	0.053 (2)	0.055 (2)	−0.0082 (16)	0.0048 (18)	0.0032 (19)

Cl1—C3	1.732 (3)	C4—C5	1.373 (5)
Cl2—C5	1.739 (3)	C4—H4A	0.93
O1—C7	1.352 (4)	C5—C6	1.392 (4)
O1—N1	1.403 (4)	C6—C7	1.458 (4)
O2—N3	1.207 (4)	C8—C9	1.468 (4)
O3—N3	1.218 (4)	C9—C14	1.384 (4)
N1—C8	1.302 (5)	C9—C10	1.390 (4)
N2—C7	1.289 (4)	C10—C11	1.378 (4)
N2—C8	1.366 (4)	C10—H10A	0.93
N3—C12	1.474 (5)	C11—C12	1.377 (5)
C1—C2	1.383 (5)	C11—H11A	0.93
C1—C6	1.398 (4)	C12—C13	1.371 (5)
C1—H1A	0.93	C13—C14	1.379 (5)
C2—C3	1.380 (5)	C13—H13A	0.93
C2—H2A	0.93	C14—H14A	0.93
C3—C4	1.381 (5)
C7—O1—N1	106.2 (2)	N2—C7—O1	112.3 (3)
C8—N1—O1	103.8 (3)	N2—C7—C6	127.0 (3)
C7—N2—C8	103.8 (3)	O1—C7—C6	120.7 (3)
O2—N3—O3	123.6 (4)	N1—C8—N2	113.9 (3)
O2—N3—C12	118.2 (3)	N1—C8—C9	122.5 (3)
O3—N3—C12	118.2 (4)	N2—C8—C9	123.5 (3)
C2—C1—C6	122.1 (3)	C14—C9—C10	119.4 (3)
C2—C1—H1A	119.0	C14—C9—C8	119.0 (3)
C6—C1—H1A	119.0	C10—C9—C8	121.6 (3)
C3—C2—C1	118.4 (3)	C11—C10—C9	121.0 (3)
C3—C2—H2A	120.8	C11—C10—H10A	119.5
C1—C2—H2A	120.8	C9—C10—H10A	119.5
C2—C3—C4	121.3 (3)	C10—C11—C12	118.0 (3)
C2—C3—Cl1	119.6 (3)	C10—C11—H11A	121.0
C4—C3—Cl1	119.1 (3)	C12—C11—H11A	121.0
C5—C4—C3	119.1 (3)	C13—C12—C11	122.3 (3)
C5—C4—H4A	120.4	C13—C12—N3	118.4 (3)
C3—C4—H4A	120.4	C11—C12—N3	119.3 (3)
C4—C5—C6	122.0 (3)	C12—C13—C14	119.2 (3)
C4—C5—Cl2	115.8 (3)	C12—C13—H13A	120.4
C6—C5—Cl2	122.1 (3)	C14—C13—H13A	120.4
C5—C6—C1	117.0 (3)	C13—C14—C9	120.1 (3)
C5—C6—C7	127.1 (3)	C13—C14—H14A	120.0
C1—C6—C7	115.8 (3)	C9—C14—H14A	120.0
C7—O1—N1—C8	−0.2 (4)	O1—N1—C8—N2	0.1 (4)
C6—C1—C2—C3	−0.3 (5)	O1—N1—C8—C9	−177.5 (3)
C1—C2—C3—C4	0.4 (5)	C7—N2—C8—N1	0.2 (4)
C1—C2—C3—Cl1	179.9 (3)	C7—N2—C8—C9	177.7 (3)
C2—C3—C4—C5	−0.6 (5)	N1—C8—C9—C14	176.5 (4)
Cl1—C3—C4—C5	179.9 (3)	N2—C8—C9—C14	−0.8 (5)
C3—C4—C5—C6	0.7 (5)	N1—C8—C9—C10	−2.4 (5)
C3—C4—C5—Cl2	178.3 (3)	N2—C8—C9—C10	−179.7 (3)
C4—C5—C6—C1	−0.6 (5)	C14—C9—C10—C11	0.0 (5)
Cl2—C5—C6—C1	−178.0 (3)	C8—C9—C10—C11	178.9 (3)
C4—C5—C6—C7	178.5 (3)	C9—C10—C11—C12	−1.0 (5)
Cl2—C5—C6—C7	1.0 (5)	C10—C11—C12—C13	0.6 (5)
C2—C1—C6—C5	0.4 (5)	C10—C11—C12—N3	−178.3 (3)
C2—C1—C6—C7	−178.8 (3)	O2—N3—C12—C13	171.1 (4)
C8—N2—C7—O1	−0.3 (4)	O3—N3—C12—C13	−9.9 (6)
C8—N2—C7—C6	179.1 (3)	O2—N3—C12—C11	−9.9 (5)
N1—O1—C7—N2	0.4 (4)	O3—N3—C12—C11	169.0 (4)
N1—O1—C7—C6	−179.1 (3)	C11—C12—C13—C14	0.8 (6)
C5—C6—C7—N2	−174.0 (4)	N3—C12—C13—C14	179.7 (3)
C1—C6—C7—N2	5.0 (5)	C12—C13—C14—C9	−1.8 (6)
C5—C6—C7—O1	5.3 (5)	C10—C9—C14—C13	1.4 (6)
C1—C6—C7—O1	−175.6 (3)	C8—C9—C14—C13	−177.5 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···N1i	0.93	2.54	3.338 (5)	144

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13A⋯N1i	0.93	2.54	3.338 (5)	144

Symmetry code: (i) .