2,3-Dibromo-3-phenyl-1-(3-phenyl­sydnon-4-yl)propan-1-one

Hoong-Kun Fun; Madhukar Hemamalini; Nithinchandra; Balakrishna Kalluraya

doi:10.1107/S1600536811008026

. 2011 Mar 9;67(Pt 4):o814. doi: 10.1107/S1600536811008026

2,3-Dibromo-3-phenyl-1-(3-phenylsydnon-4-yl)propan-1-one

Hoong-Kun Fun ^a,^*,^‡, Madhukar Hemamalini ^a, Nithinchandra ^b, Balakrishna Kalluraya ^b

PMCID: PMC3099808 PMID: 21754100

Abstract

In the title compound [systematic name: 4-(2,3-dibromo-3-phenylpropanoyl)-3-phenyl-1,2,3-oxadiazol-3-ylium-5-olate], C₁₇H₁₂Br₂N₂O₃, the oxadiazole ring is essentially planar, with a maximum deviation of 0.001 (3) Å. The central oxadiazole ring makes dihedral angles of 73.3 (2) and 29.0 (2)° with the adjacent and remote phenyl rings, respectively. In the crystal, adjacent molecules are connected by C—H⋯O hydrogen bonds, forming a supramolecular chain along the c axis. There is an intramolecular C—H⋯O hydrogen bond, which generates an S(6) ring motif.

Related literature

For applications of sydnones, see: Rai et al. (2008 ▶); Jyothi et al. (2008 ▶). For details of chalcones, see: Rai et al. (2007 ▶).

Experimental

Crystal data

C₁₇H₁₂Br₂N₂O₃
M _r = 452.11
Monoclinic,
a = 11.9109 (3) Å
b = 17.5018 (3) Å
c = 8.5365 (2) Å
β = 94.960 (1)°
V = 1772.87 (7) Å³
Z = 4
Mo Kα radiation
μ = 4.59 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.04 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T _min = 0.341, T _max = 0.849
23853 measured reflections
4082 independent reflections
1912 reflections with I > 2σ(I)
R _int = 0.068

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.104
S = 0.98
4082 reflections
217 parameters
H-atom parameters constrained
Δρ_max = 0.48 e Å⁻³
Δρ_min = −0.44 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 datablocks global, I. DOI: 10.1107/S1600536811008026/is2684sup1.cif

e-67-0o814-sup1.cif^{(19.1KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811008026/is2684Isup2.hkl

e-67-0o814-Isup2.hkl^{(200.1KB, 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
C10—H10A⋯O2	0.98	2.35	3.028 (6)	126
C13—H13A⋯O2ⁱ	0.93	2.49	3.312 (6)	147

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Symmetry code: (i) Inline graphic .

Acknowledgments

HKF and MH thank the Malaysian Government and Universiti Sains Malaysia for the Research University grant No. 1001/PFIZIK/811160. MH thanks Universiti Sains Malaysia for a post-doctoral research fellowship.

supplementary crystallographic information

Comment

Sydnones constitute a well-defined class of mesoionic compounds that contain the 1,2,3-oxadiazole ring system. The study of sydnones still remains a field of interest because of their electronic structure and also because of the varied types of biological activities (Rai et al., 2008). Recently, sydnone derivatives were found to exhibit promising anti-microbial properties (Jyothi et al., 2008). Chalcones were obtained by the base-catalyzed condensation of 4-acetyl-3-aryl sydnones with aromatic aldehydes in alcoholic medium employing sodium hydroxide as catalyst at 0–5 °C. Bromination of chalcones with bromine in glacial acetic acid afforded dibromo chalcones (Rai et al., 2007).

The molecular structure of the title compound is shown in Fig. 1. The oxadiazole (N1/N2/O1/C7/C8) ring is essentially planar, with a maximum deviation of 0.001 (3) Å for atom O1. The central oxadiazole (N1/N2/O1/C7/C8) ring makes dihedral angles of 73.3 (2)° and 29.0 (2)° with the attached phenyl (C1–C6) and the terminal phenyl (C12–C17) rings, respectively.

In the crystal, (Fig. 2), the adjacent molecules are connected by intra and intermolecular C10—H10A···O2 and C13—H13A···O2 (Table 1) hydrogen bonds forming supramolecular chains along the c-axis. There is an intramolecular C—H···O hydrogen bond, which generates an S(6) ring motif.

Experimental

1-(3¹-Phenylsydnon-4¹-yl)-3-(phenyl)-propen-1-one (0.01 mol) was dissolved in glacial acetic acid (2–30 ml) by gentle warming. A solution of bromine in glacial acetic acid (30% w/v) was added to it with constant stirring till the yellow color of the bromine persisted. The reaction mixture was stirred at room temperature for 1-2 hours. The solid which separated was filtered, washed with methanol and dried. It was then recrystallized from ethanol. Crystals suitable for X-ray analysis were obtained from 1:2 mixtures of DMF and ethanol by slow evaporation.