1-[2-(4-Chloro­phen­yl)-5-phenyl-2,3-dihydro-1,3,4-oxadiazol-3-yl]ethanone

Hoong-Kun Fun; Suhana Arshad; P C Shyma; Balakrishna Kalluraya; T Arulmoli

doi:10.1107/S1600536812023100

. 2012 May 26;68(Pt 6):o1901. doi: 10.1107/S1600536812023100

1-[2-(4-Chlorophenyl)-5-phenyl-2,3-dihydro-1,3,4-oxadiazol-3-yl]ethanone

Hoong-Kun Fun ^a,^*,^‡, Suhana Arshad ^a, P C Shyma ^b, Balakrishna Kalluraya ^b, T Arulmoli ^c

PMCID: PMC3379458 PMID: 22719656

Abstract

In the title compound, C₁₆H₁₄ClN₃O₂, the 2,3-dihydro-1,3,4-oxadiazole ring [maximum deviation = 0.030 (1) Å] and the pyridine ring [maximum deviation = 0.012 (1) Å] are inclined slightly to one another, making a dihedral angle of 11.91 (5)°. The chloro-substituted phenyl ring is almost perpendicular to the 2,3-dihydro-1,3,4-oxadiazole and pyridine rings at dihedral angles of 86.86 (5) and 75.26 (5)°, respectively. In the crystal, π–π [centroid–centroid distance = 3.7311 (6) Å] and C—H⋯π interactions are observed.

Related literature

For the biological activity of 3-acetyl-2,5-disubstituted-2,3-dihydro-1,3,4-oxadiazoline ring systems, see: Rakesh & Prabhakar (2009 ▶); Priya et al. (2007 ▶); Bhatia & Gupta (2011 ▶); Vijesh et al. (2011 ▶); Galil & Amr (2000 ▶). For related structures, see: Yehye et al. (2010 ▶); Ono et al. (2009 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). graphic file with name e-68-o1901-scheme1.jpg

Experimental

Crystal data

C₁₆H₁₄ClN₃O₂
M _r = 315.75
Triclinic,
a = 5.8623 (2) Å
b = 10.9912 (5) Å
c = 12.2815 (5) Å
α = 68.214 (1)°
β = 84.707 (1)°
γ = 87.623 (1)°
V = 731.67 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 100 K
0.40 × 0.22 × 0.14 mm

Data collection

Bruker SMART APEXII DUO CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.899, T _max = 0.962
19562 measured reflections
5301 independent reflections
4768 reflections with I > 2σ(I)
R _int = 0.021

Refinement

R[F ² > 2σ(F ²)] = 0.037
wR(F ²) = 0.116
S = 1.02
5301 reflections
195 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.64 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 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812023100/hb6803sup1.cif

e-68-o1901-sup1.cif^{(24.7KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812023100/hb6803Isup2.hkl

e-68-o1901-Isup2.hkl^{(259.6KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812023100/hb6803Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg3 is the centroid of the C8–C13 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C16—H16A⋯Cg3ⁱ	0.98	2.65	3.4360 (13)	138

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Symmetry code: (i) Inline graphic .

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). SA also thanks the Malaysian Government and USM for the Academic Staff Training Scheme (ASTS) award.

supplementary crystallographic information

Comment

Oxadiazole, a five-membered heterocyclic nucleus, has attracted a wide attention of the chemists in search for the new therapeutic molecules. A number of therapeutic agents such as HIV-integrase inhibitor Raltegravir, a nitrofuran antibacterial Furamizole, antihypertensive agents like Tiodazosin and Nesapidil are based on the 1,3,4-oxadiazole moiety. The 3-acetyl-2,5-disubstituted-2,3- dihydro-1,3,4-oxadiazoline ring systems are associated with diverse biological properties such as analgesic, anti-inflammatory, anticancer, anti-HIV, antibacterial, antitubercular activities (Rakesh & Prabhakar, 2009; Priya et al., 2007; Bhatia & Gupta, 2011). Further, substituted pyridines have showed significant biological activities (Vijesh et al., 2011; Galil & Amr, 2000). Pyridine-derived pharmaceuticals include Atazanavir and Imatinib mesylate which are recommended for the treatment of HIV and chronic myelogenous leukemia respectively. Keeping in view of the therapeutic importance of 1,3,4-oxadiazoles and pyridines, we synthesized the title compound to study its crystal structure.

In the molecular structure (Fig. 1), the 2,3-dihydro-1,3,4-oxadiazole ring [O1/N2/N3/C6/C7, with a maximum deviation of 0.030 (1) Å at atom C7] and the pyridine ring [N1/C1–C5, with a maximum deviation of 0.012 (1) Å at atom C3 and C5] are slightly inclined to one another, making a dihedral angle of 11.91 (5)°. Meanwhile, the chloro-substituted phenyl ring (C8–C13) is almost perpendicular to the 2,3-dihydro-1,3,4-oxadiazole and pyridine rings at dihedral angles of 86.86 (5) and 75.26 (5)°, respectively. Bond lengths and angles are within normal ranges and are comparable to related structures (Yehye et al., 2010; Ono et al., 2009).

The crystal packing is shown in Fig. 2. π–π interactions are observed with centroid to centroid distance Cg1···Cg2 = 3.7311 (6) Å; symmetry code: 1 - x, 2 - y,1 - z. The crystal structure also features intermolecular C16—H16A···Cg3 (Table 1) interactions (Cg1, Cg2 and Cg3 are the centroids of O1/N2/N3/C6/C7, N1/C1–C5 and C8–C13 rings, respectively).

Experimental

Schiff base, N'-[(1E)-(4-chlorophenyl)methylene]-4- methylbenzohydrazide (0.5 g, 0.0018 mol) was refluxed with acetic anhydride (3 ml) for 1 h. After the completion of reaction, the excess acetic anhydride was distilled out at reduced pressure and the residue obtained was poured into ice cold water. The solid that was separated out was filtered, washed with water and dried. The crude product was recrystallized from hot ethanol in the form of yellow blocks (0.38 g, 76%). M.p.: 395–397 K.