3-(2,4-Dichloro­phen­yl)-5-phenyl-1,2,4-oxadiazole

Hoong-Kun Fun; Mohd Mustaqim Rosli; Sankappa Rai; Arun M Isloor; Prakash Shetty

doi:10.1107/S160053681000927X

. 2010 Mar 17;66(Pt 4):o851. doi: 10.1107/S160053681000927X

3-(2,4-Dichlorophenyl)-5-phenyl-1,2,4-oxadiazole

Hoong-Kun Fun ^a,^*,^‡, Mohd Mustaqim Rosli ^a, Sankappa Rai ^b, Arun M Isloor ^c, Prakash Shetty ^d

PMCID: PMC2984080 PMID: 21580675

Abstract

In the title compound, C₁₄H₈Cl₂N₂O, 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, molecules are linked into chains along the c axis by C—H⋯Cl interactions. 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 _r = 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
Δρ_max = 0.55 e Å⁻³
Δρ_min = −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 ▶).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681000927X/sj2743sup1.cif

e-66-0o851-sup1.cif^{(17.7KB, cif)}

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

e-66-0o851-Isup2.hkl^{(132.2KB, hkl)}

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

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)

Open in a new tab

Symmetry code: (i) Inline graphic .

Acknowledgments

AMI is grateful to Professor Sandeep Sancheti, Director, National Institute of Technology-Karnataka, India for his encouragement and providing research facilities. FHK and MMR thank Universiti Sains Malaysia for the Research University Golden Goose grant (No. 1001/PFIZIK/811012).

supplementary crystallographic information

Comment

Heterocyclic compounds are becoming increasingly important in recent years due to their pharmacological activities (Isloor et al. 2010). Nitrogen- and oxygen-containing five/six membered heterocyclic compounds are of enormous significance in the field of medicinal chemistry (Chandrakantha et al., 2010). Oxadiazoles play a very vital role in the preparation of various biologically active drugs with anti-inflammatory (Andersen et al., 1994), anti-cancer (Showell et al., 1991), anti-HIV (Watjen et al., 1989), anti-diabetic and anti-microbial (Swain et al., 1991) activities. The results of biological studies showed that oxadiazole derivatives also possess maximum anti-inflammatory, analgesic and minimum ulcerogenic and lipid per-oxidation (Clitherow et al., 1996) properties.

The geometrical parameters of (I) are within the normal range and comparable with those for a related structure (Wang et al., 2006). The mean plane of of the oxadiazole ring (C7/C8/N1/N2/O1) is almost coplanar with the C9-C14 benzene ring [dihedral angle = 2.3 (1)°] but slightly twisted with the C1-C6 benzene ring [dihedral angle = 9.5 (1)°].

The C-H···Cl (Table 1) interactions link the molecules into infinite chains along the c-axis and these chains are stacked along the a-axis.

Experimental

The title compound was prepared by heating a solution of 2,4-dichloro- N'-hydroxy-benzamidine (1 g,0.0042 mol) and benzoylchloride (0.65 g.0.004 mol) in pyridine (30 ml). The reaction mixture was heated at 114 °C for 1.5 hour and concentrated under vacuum. Further purification was done by column chromatography. The solid obtained was recrystalised using dichloromethane.Yield: 1 g (76%), Melting point 413-415 K.