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

In the title compound, C(9)H(6)Cl(2)N(2)O, the dihedral angle between the oxadiazole and benzene rings is 1.7 (2)°. In the crystal, the mol-ecules are linked into chains along the b axis by short inter-molecular Cl⋯O contacts [3.019 (3) Å].

Related literature

For general background and the biological activity of oxa­diazole compounds, see: Andersen et al. (1994 ▶); Clitherow et al. (1996 ▶); Showell et al. (1991 ▶); Swain et al. (1991 ▶); Watjen et al. (1989 ▶). 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

C9H6Cl2N2O

M = 229.06

Monoclinic,

a = 3.8252 (7) Å

b = 21.678 (4) Å

c = 11.0833 (19) Å

β = 92.421 (4)°

V = 918.3 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.67 mm−1

T = 100 K

0.28 × 0.17 × 0.11 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.833, T max = 0.929

7920 measured reflections

2076 independent reflections

1709 reflections with I > 2σ(I)

R int = 0.048

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.155

S = 1.20

2076 reflections

128 parameters

H-atom parameters constrained

Δρmax = 0.72 e Å−3

Δρmin = −0.56 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/S1600536810007932/ci5045sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810007932/ci5045Isup2.hkl

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

C9H6Cl2N2O	F(000) = 464
Mr = 229.06	Dx = 1.657 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3719 reflections
a = 3.8252 (7) Å	θ = 2.6–31.1°
b = 21.678 (4) Å	µ = 0.67 mm−1
c = 11.0833 (19) Å	T = 100 K
β = 92.421 (4)°	Block, colourless
V = 918.3 (3) Å3	0.28 × 0.17 × 0.11 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	2076 independent reflections
Radiation source: fine-focus sealed tube	1709 reflections with I > 2σ(I)
graphite	Rint = 0.048
φ and ω scans	θmax = 27.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −4→4
Tmin = 0.833, Tmax = 0.929	k = −26→28
7920 measured reflections	l = −13→14

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155	H-atom parameters constrained
S = 1.20	w = 1/[σ2(Fo2) + (0.0428P)2 + 4.0517P] where P = (Fo2 + 2Fc2)/3
2076 reflections	(Δ/σ)max = 0.001
128 parameters	Δρmax = 0.72 e Å−3
0 restraints	Δρmin = −0.56 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	0.2530 (2)	0.40084 (4)	0.92173 (8)	0.0163 (2)
Cl2	0.1238 (3)	0.63730 (4)	0.78985 (9)	0.0185 (3)
O1	−0.2054 (8)	0.27327 (13)	0.6574 (3)	0.0220 (7)
N1	−0.3467 (8)	0.35961 (15)	0.5636 (3)	0.0158 (7)
N2	−0.0709 (10)	0.32171 (16)	0.7322 (3)	0.0194 (7)
C1	−0.3637 (11)	0.30045 (18)	0.5605 (4)	0.0173 (8)
C2	−0.1651 (10)	0.37119 (18)	0.6715 (3)	0.0140 (8)
C3	−0.0869 (9)	0.43519 (17)	0.7088 (3)	0.0124 (7)
C4	0.0928 (10)	0.45392 (18)	0.8165 (3)	0.0137 (8)
C5	0.1523 (9)	0.51553 (18)	0.8418 (4)	0.0136 (7)
H5A	0.2684	0.5272	0.9136	0.016*
C6	0.0369 (10)	0.56000 (17)	0.7588 (3)	0.0127 (7)
C7	−0.1429 (10)	0.54398 (18)	0.6533 (4)	0.0151 (8)
H7A	−0.2240	0.5740	0.5990	0.018*
C8	−0.1993 (10)	0.48214 (18)	0.6303 (4)	0.0153 (8)
H8A	−0.3186	0.4712	0.5586	0.018*
C9	−0.5226 (12)	0.2592 (2)	0.4666 (4)	0.0237 (9)
H9A	−0.6428	0.2835	0.4055	0.036*
H9B	−0.6856	0.2319	0.5028	0.036*
H9C	−0.3422	0.2354	0.4308	0.036*

	U11	U22	U33	U12	U13	U23
Cl1	0.0168 (5)	0.0182 (5)	0.0138 (5)	0.0028 (3)	−0.0011 (3)	0.0023 (4)
Cl2	0.0197 (5)	0.0140 (4)	0.0219 (5)	−0.0024 (3)	0.0025 (4)	−0.0017 (4)
O1	0.0309 (17)	0.0139 (14)	0.0213 (15)	−0.0017 (12)	0.0017 (12)	−0.0018 (12)
N1	0.0130 (15)	0.0175 (16)	0.0172 (17)	0.0000 (12)	0.0018 (12)	−0.0022 (13)
N2	0.0257 (19)	0.0147 (16)	0.0178 (18)	−0.0002 (14)	0.0018 (14)	−0.0032 (13)
C1	0.0148 (19)	0.0194 (19)	0.018 (2)	0.0000 (15)	0.0051 (15)	−0.0007 (15)
C2	0.0103 (17)	0.0185 (19)	0.0138 (18)	0.0022 (14)	0.0081 (14)	0.0000 (14)
C3	0.0078 (17)	0.0152 (18)	0.0150 (18)	0.0009 (13)	0.0080 (14)	−0.0011 (14)
C4	0.0126 (18)	0.0171 (19)	0.0119 (19)	0.0043 (13)	0.0054 (14)	0.0016 (14)
C5	0.0070 (16)	0.0208 (19)	0.0132 (18)	0.0017 (14)	0.0022 (13)	−0.0021 (15)
C6	0.0106 (17)	0.0134 (17)	0.0144 (18)	−0.0008 (13)	0.0033 (13)	−0.0027 (14)
C7	0.0106 (18)	0.0174 (19)	0.0177 (19)	0.0033 (14)	0.0056 (14)	0.0033 (15)
C8	0.0114 (17)	0.0181 (19)	0.017 (2)	0.0005 (14)	0.0055 (14)	0.0004 (15)
C9	0.025 (2)	0.018 (2)	0.029 (2)	−0.0030 (16)	0.0041 (18)	−0.0072 (17)

Cl1—C4	1.732 (4)	C4—C5	1.382 (5)
Cl2—C6	1.740 (4)	C5—C6	1.391 (5)
O1—C1	1.346 (5)	C5—H5A	0.93
O1—N2	1.421 (4)	C6—C7	1.376 (5)
N1—C1	1.285 (5)	C7—C8	1.380 (6)
N1—C2	1.381 (5)	C7—H7A	0.93
N2—C2	1.308 (5)	C8—H8A	0.93
C1—C9	1.483 (6)	C9—H9A	0.96
C2—C3	1.475 (5)	C9—H9B	0.96
C3—C8	1.396 (5)	C9—H9C	0.96
C3—C4	1.411 (5)
C1—O1—N2	106.4 (3)	C6—C5—H5A	120.3
C1—N1—C2	103.2 (3)	C7—C6—C5	121.3 (4)
C2—N2—O1	102.8 (3)	C7—C6—Cl2	119.7 (3)
N1—C1—O1	113.3 (4)	C5—C6—Cl2	119.0 (3)
N1—C1—C9	129.8 (4)	C6—C7—C8	118.1 (4)
O1—C1—C9	116.9 (4)	C6—C7—H7A	121.0
N2—C2—N1	114.4 (4)	C8—C7—H7A	121.0
N2—C2—C3	125.4 (4)	C7—C8—C3	123.5 (4)
N1—C2—C3	120.2 (3)	C7—C8—H8A	118.3
C8—C3—C4	116.4 (3)	C3—C8—H8A	118.3
C8—C3—C2	117.2 (3)	C1—C9—H9A	109.5
C4—C3—C2	126.4 (3)	C1—C9—H9B	109.5
C5—C4—C3	121.3 (3)	H9A—C9—H9B	109.5
C5—C4—Cl1	117.1 (3)	C1—C9—H9C	109.5
C3—C4—Cl1	121.6 (3)	H9A—C9—H9C	109.5
C4—C5—C6	119.4 (3)	H9B—C9—H9C	109.5
C4—C5—H5A	120.3
C1—O1—N2—C2	0.1 (4)	C8—C3—C4—C5	0.0 (5)
C2—N1—C1—O1	−0.4 (5)	C2—C3—C4—C5	179.8 (3)
C2—N1—C1—C9	−179.1 (4)	C8—C3—C4—Cl1	−179.1 (3)
N2—O1—C1—N1	0.2 (5)	C2—C3—C4—Cl1	0.6 (5)
N2—O1—C1—C9	179.1 (3)	C3—C4—C5—C6	−0.8 (6)
O1—N2—C2—N1	−0.4 (4)	Cl1—C4—C5—C6	178.4 (3)
O1—N2—C2—C3	−179.3 (3)	C4—C5—C6—C7	1.6 (6)
C1—N1—C2—N2	0.5 (5)	C4—C5—C6—Cl2	−178.3 (3)
C1—N1—C2—C3	179.5 (3)	C5—C6—C7—C8	−1.5 (6)
N2—C2—C3—C8	178.0 (4)	Cl2—C6—C7—C8	178.4 (3)
N1—C2—C3—C8	−0.8 (5)	C6—C7—C8—C3	0.7 (6)
N2—C2—C3—C4	−1.8 (6)	C4—C3—C8—C7	0.1 (6)
N1—C2—C3—C4	179.4 (4)	C2—C3—C8—C7	−179.7 (4)