2,3-Dibromo-3-(5-nitro-2-fur­yl)-1-phenyl­propan-1-one

Tara Shahani; Hoong-Kun Fun; Nithinchandra; Balakrishna Kalluraya

doi:10.1107/S1600536811003552

. 2011 Feb 2;67(Pt 3):o546. doi: 10.1107/S1600536811003552

2,3-Dibromo-3-(5-nitro-2-furyl)-1-phenylpropan-1-one

Tara Shahani ^a, Hoong-Kun Fun ^a,^*,^‡, Nithinchandra ^b, Balakrishna Kalluraya ^b

PMCID: PMC3052152 PMID: 21522313

Abstract

In the title compound, C₁₃H₉Br₂NO₄, the phenyl and 2-nitrofuran rings are linked by a 2,3-dibromopropanal group, six atoms of which, including a furyl C atom, are disordered over two positions with a site-occupancy ratio of 0.733 (11):0.267 (11). The dihedral angle between the furan [maximum deviation = 0.028 (4) Å] and phenyl rings in the major component is 16.9 (3)°. In the minor component, the corresponding values are 0.87 (4) Å and 23.3 (5)°. In the crystal, intermolecular C—H⋯O hydrogen bonds link the molecules into two-dimensional arrays parallel to the ab plane.

Related literature

For the biological activity of sydnones, see: Holla et al. (1986 ▶, 1987 ▶, 1992 ▶); Rai et al. (2008 ▶). For related structures, see: Fun et al. (2010 ▶, 2011 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C₁₃H₉Br₂NO₄
M _r = 403.03
Triclinic,
a = 8.6939 (7) Å
b = 8.7834 (8) Å
c = 10.4722 (9) Å
α = 89.334 (2)°
β = 69.846 (2)°
γ = 68.114 (2)°
V = 690.32 (10) Å³
Z = 2
Mo Kα radiation
μ = 5.88 mm⁻¹
T = 100 K
0.28 × 0.18 × 0.08 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.292, T _max = 0.644
10644 measured reflections
4015 independent reflections
3390 reflections with I > 2σ(I)
R _int = 0.030

Refinement

R[F ² > 2σ(F ²)] = 0.043
wR(F ²) = 0.100
S = 1.33
4015 reflections
216 parameters
H-atom parameters constrained
Δρ_max = 0.71 e Å⁻³
Δρ_min = −0.60 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/S1600536811003552/sj5095sup1.cif

e-67-0o546-sup1.cif^{(20.9KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811003552/sj5095Isup2.hkl

e-67-0o546-Isup2.hkl^{(196.8KB, 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
C9A—H9AA⋯O1ⁱ	0.98	2.25	3.098 (6)	145
C4—H4A⋯O4ⁱⁱ	0.93	2.46	3.200 (6)	136

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

Acknowledgments

HKF and TSH thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160). TSH also thanks USM for the award of a research fellowship.

supplementary crystallographic information

Comment

Nitrofurans belong to a class of synthetic compounds characterized by the presence of the 5-nitro-2-furyl group. The presence of a nitro group at the 5-position of the molecule conferred antibacterial activity (Holla et al.1986). A large number of nitrofurans have attained commercial utility as antibacterial agents in humans and in veterinary medicine because of their broad spectrum of activity (Holla & Kalluraya et al.1992; Holla et al. 1987). Dibromopropanones were obtained by the bromination of 1-aryl-3-(5-nitro-2-furyl)-2-propen-1-ones. Acid-catalysed condensation of acetophenones with nitrofural diacetate in acetic acid yielded the required 1-aryl-3-(5-nitro-2-furyl)-2-propen-1-ones known as chalcones (Rai et al., 2008).

The title compound, C₁₃H₉Br₂NO₄, (Fig. 1), consist of phenyl (C1–C6) and 2-nitrofuran (C10–C13/O2–O4/N1) rings linked by a 2,3-dibromopropanal group (O1/C7–C9/Br1/Br2). Six atoms (C8–C10/Br1/Br2/O2) of this linking group including a furyl C atom are disordered over two positions with a site-occupancy ratio of 0.733 (11): 0.267 (11). The dihedral angle between the furan (C11–C13/O2/C10) (maximum deviation of 0.028 (4) Å of at atom C12) and phenyl rings in the major component is 16.9 (3)°. In the minor component, the corresponding values are 0.87 (4) Å at atom C12 and 23.3 (5)°. Bond lengths (Allen et al., 1987) and angles are normal and comparable to those in related structures (Fun et al., 2010, 2011).

In the crystal packing (Fig. 2), intermolecular C9A—H9AA···O1 and C4—H4A···O4 hydrogen bonds (Table 1) link the molecules into two-dimensional arrays parallel to the ab plane.

Experimental

1-Phenyl-3-(5-nitro-2-furyl)-2-propen-1-one (0.01 mol) was dissolved in glacial acetic acid (25 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 kept aside at room temperature for overnight. Crystals of dibromopropanone that separated out were collected by filtration and washed with petroleum ether and dried. They were then recrystallized from glacial acetic acid. Crystals suitable for X-ray analysis were obtained from 1:2 mixtures of DMF and ethanol by slow evaporation.