2,3-Dibromo-1-(4-methyl­phen­yl)-3-(5-nitro­furan-2-yl)propan-1-one

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

doi:10.1107/S1600536810050488

. 2010 Dec 11;67(Pt 1):o79. doi: 10.1107/S1600536810050488

2,3-Dibromo-1-(4-methylphenyl)-3-(5-nitrofuran-2-yl)propan-1-one

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

PMCID: PMC3050337 PMID: 21522790

Abstract

In the title compound, C₁₄H₁₁Br₂NO₄, the whole molecule is disordered over two positions with a refined occupancy ratio of 0.539 (9):0.461 (9). The 2-nitrofuran and toluene groups are approximately planar, with maximum deviations of 0.176 (11) and 0.121 (14) Å, respectively, in the major component and 0.208 (11) and 0.30 (17) Å in the minor component. The dihedral angles between the 2-nitrofuran and toluene groups are 8.7 (5) and 8.0 (9)° for the major and minor components, respectively. In the crystal, weak intermolecular C—H⋯O interactions connect molecules into a three-dimensional network, generating R ₂ ¹(6) ring motifs.

Related literature

For the biological activity of nitrofurans, see: Holla et al. (1986 ▶, 1987 ▶, 1992 ▶); Hegde et al. (2006 ▶); Rai et al. (2008 ▶). For a related structure, see: Fun et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶). For standard bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C₁₄H₁₁Br₂NO₄
M _r = 417.06
Triclinic,
a = 8.7766 (3) Å
b = 9.0386 (3) Å
c = 10.4841 (3) Å
α = 87.601 (2)°
β = 75.505 (2)°
γ = 69.554 (2)°
V = 753.53 (4) Å³
Z = 2
Mo Kα radiation
μ = 5.39 mm⁻¹
T = 100 K
0.47 × 0.21 × 0.13 mm

Data collection

Bruker APEXII DUO CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T _min = 0.184, T _max = 0.550
10357 measured reflections
3465 independent reflections
2729 reflections with I > 2σ(I)
R _int = 0.026

Refinement

R[F ² > 2σ(F ²)] = 0.041
wR(F ²) = 0.103
S = 1.19
3465 reflections
274 parameters
658 restraints
H-atom parameters constrained
Δρ_max = 0.88 e Å⁻³
Δρ_min = −0.40 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/S1600536810050488/lh5178sup1.cif

e-67-00o79-sup1.cif^{(25.2KB, cif)}

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810050488/lh5178Isup2.hkl

e-67-00o79-Isup2.hkl^{(169.9KB, 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
C2A—H2AA⋯O3Aⁱ	0.93	2.53	3.210 (15)	131
C3A—H3AA⋯O2Aⁱⁱ	0.93	2.51	3.216 (12)	133
C6A—H6AA⋯O2Aⁱⁱ	0.98	2.33	3.217 (10)	151
C13A—H13A⋯O3Aⁱⁱⁱ	0.93	2.55	3.434 (13)	158

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

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 are a class of synthetic compounds characterized by the presence of 5-nitro-2-furyl group. The presence of nitro group in position-5 of the molecule conferred antibacterial activity (Holla et al.1986). A number of nitrofurans have attained commercial utility as antibacterial agents in humans and in veterinary medicine because of their broad spectrum of activities (Holla & Kalluraya et al., 1992; Holla et al., 1987). The incorporation of 5-nitrofuran or 5-nitrothiophene moiety into various heterocyclic systems has found to increase their biological activities. We have reported few heterocyclic systems carrying a 5-nitrofuran moiety as potent antimicrobial agents (Hegde et al., 2006). During the synthetic procedures, the 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 (chalcones) (Rai et al., 2008).

In the title compound (Fig. 1), the whole molecule is disordered over two positions with a refined occupancy ratio of 0539 (9):0.461 (9) The molecule consists of a 2-nitrofuran (C1–C3/C5/N1/O1/O3/O4) group, a toluene group which (C9–C15) and one 2, 3-dibromopropanal (C6–C9/Br1/Br2/O2) moiety. Both ring groups are essentially planar (maximum deviation of 0.176 (11) and 0.121 (14) Å in the major component and 0.208 (11) and 0.30 (17) Å in the minor component for the 2-nitrofuran and toluene groups respectively). The bond lengths (Allen et al., 1987) and angles are within normal ranges and are comparable to a closely related structure (Fun et al., 2010).

In the crystal packing (Fig. 2), intermolecular C3A—H3A···O2Aⁱⁱ and C6A—H6A···O2Aⁱⁱ hydrogen bonds connect neighbouring molecules generating R₂¹(6) ring motifs (Bernstein et al., 1995) (Table 1). These dimers are linked into a three-dimensional network by intermolecular C2A—H2AA···O3Aⁱ and C13A—H13A···O3Aⁱⁱⁱ hydrogen bonds (Table 1).

Experimental

1-(4-Methylphenyl)-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 dibromopropanones which separated out were collected by filtration and washed with ethanol and dried and 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.