4-[5-(4-Benzoyl­oxyphen­yl)-1,2,4-oxa­diazol-3-yl]phenyl benzoate

B C Manjunath; S Madan Kumar; K S Vinay Kumar; M Prabhuswamy; M P Sadashiva; N K Lokanath

doi:10.1107/S1600536813006922

. 2013 Mar 16;69(Pt 4):o543. doi: 10.1107/S1600536813006922

4-[5-(4-Benzoyloxyphenyl)-1,2,4-oxadiazol-3-yl]phenyl benzoate

B C Manjunath ^a, S Madan Kumar ^a, K S Vinay Kumar ^b, M Prabhuswamy ^a, M P Sadashiva ^b, N K Lokanath ^a,^*

PMCID: PMC3629595 PMID: 23634082

Abstract

In the title compound, C₂₈H₁₈N₂O₅, the dihedral angle between the terminal benzoate rings is 20.67 (12)°. The central oxadiazole ring is almost coplanar with its two benzene ring substituents, making dihedral angles of 4.80 (16) and 5.82 (16)°. In the crystal, pairs of C—H⋯O hydrogen bonds form inversion dimers with R ₂ ²(40) ring motifs. The structure also features C—H⋯O, C—H⋯π and π–π interactions [centroid–centroid separation = 3.695 (4) Å].

Related literature

For the use of oxadiazole derivatives as antimicrobial agents, see: Dhol et al. (2005 ▶) and for a related structure, see: Emmerling et al. (2006 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₂₈H₁₈N₂O₅
M _r = 462.44
Monoclinic,
a = 21.069 (18) Å
b = 6.063 (5) Å
c = 18.727 (16) Å
β = 107.159 (13)°
V = 2286 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 300 K
0.23 × 0.23 × 0.22 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
21331 measured reflections
4513 independent reflections
2518 reflections with I > 2σ(I)
R _int = 0.060

Refinement

R[F ² > 2σ(F ²)] = 0.068
wR(F ²) = 0.191
S = 1.03
4513 reflections
316 parameters
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and Mercury.

Supplementary Material

Click here for additional data file.^{(31KB, cif)}

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813006922/sj5303sup1.cif

e-69-0o543-sup1.cif^{(31KB, cif)}

Click here for additional data file.^{(221.1KB, hkl)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006922/sj5303Isup2.hkl

e-69-0o543-Isup2.hkl^{(221.1KB, hkl)}

Click here for additional data file.^{(8.4KB, cml)}

Supplementary material file. DOI: 10.1107/S1600536813006922/sj5303Isup3.cml

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

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

Cg3 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O5ⁱ	0.93	2.57	3.407 (5)	150
C25—H25⋯O3ⁱⁱ	0.93	2.34	3.222 (6)	158
C28—H28⋯Cg3ⁱⁱⁱ	0.93	2.96	3.678 (5)	135

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

MKS thanks theUGC–BRS and the UoM for the award of a fellowship, and MPS gratefully acknowledges financial support (grant F. No. 37–456/2009[SR]) from the UGC, India.

supplementary crystallographic information

Comment

Oxadiazole derivatives are known to act as antimicrobial agents (Dhol, et al., 2005). In the title oxadiazole derivative, C₂₈H₁₈N₂O₅, (Fig. 1), the geometry of the oxodiazole ring is comparable to that found in similar molecules (Emmerling et al., 2006). The dihedral angle between the two terminal benzoate rings is 20.67 (12)°. The central oxadiazole ring and its two benzene ring substituents are almost co-planar with the dihedral angles between the O1/C1/N1/C2/N2/ oxadiazole ring and the C3/C4/C5/C6/C7/C8 and C16/C17/C18/C19/C20/C21 benzene rings are 4.80 (16)° and 5.82 (16)° respectively.

C25–H25···O3 hydrogen bonds (Table 1) link adjacent molecules to form inversion dimers with R²₂(40) ring motifs (Bernstein et al., 1995). An additional C18–H18···O5 contact together with a C28—H28···Cg3 interaction (Table 1) and a Cg1···Cg2^ivπ···π contact with a centroid-centroid distance of 3.695 (4) Å further stabilise the packing. Cg1 and Cg2 are the centroids of the O1/N1/C1/C2/N2 and C3/C4/C5/C6/C7/C8 rings, respectively and ^iv = -x + 1, -y - 1/2, -z + 1.

Experimental

4-[(E)-(hydroxyimino)methyl] phenyl benzoate (4.8 mmole) was dissolved in chloroform, N-chlorosuccinimide (5.2 mmole) was added followed by slow addition of sodium carbonate (8.8 mmole) at room temperature. Then, the resulting reaction mixture was stirred for up to 18 h. After completion of reaction (monitored by TLC), the reaction mixture was diluted with water (50 ml). The aqueous layer was extracted with ethyl acetate (3*20 ml), the combined ethyl acetate layer was washed with brine solution (2*25 ml). Then, the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford the crude product, which was further purified by column chromatography over silica gel (60–120 mesh) using hexane:ethyl acetate mixture in an 8:2 ratio as eluent. The pure compound was crystallized from ethyl acetate and hexane, to give white single crystals.

¹H NMR (DMSO-d6, 300 MHz): δ 7.33 (t, J=7.2 Hz, 2H), 7.13 (T, J=8.7 Hz, 4H), 7.02 (t, J=7.2 Hz, 2H), 6.75 (s, 2H), 4.51 (d, J=1.8 Hz, 2H), 3.08 (s, 1H).

Mass: Calc. 231.3 found: 232 (M+1). Melting point (°C): 90 (Uncorrected)