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Acta Crystallogr Sect E Struct Rep Online. 2010 November 1; 66(Pt 11): o3031–o3032.
Published online 2010 October 31. doi:  10.1107/S1600536810043850
PMCID: PMC3009355

3-(5-Nitro-2-fur­yl)-1-phenyl­prop-2-yn-1-one

Abstract

In the title compound, C13H7NO4, the 2-furyl ring is essentially planar, with a maximum deviation of 0.004 (1) Å. It is inclined at an angle of 11.69 (4)° to the benzene ring. The nitro group is slightly twisted out of the plane of the 2-furyl ring, with a dihedral angle of 5.72 (8)°. There is a short O(...)C contact of 2.8562 (8) Å (symmetry code: −x, −y, 2 − z). In the crystal packing, mol­ecules are linked via a pair of inter­molecular C—H(...)O hydrogen bonds, giving rise to an R 2 2(10) ring motif. Mol­ecules are further linked into two-dimensional networks parallel to [100] via other inter­molecular C—H(...)O hydrogen bonds. The crystal structure is consolidated by C—H(...)π inter­actions.

Related literature

For general background to the biological activity of nitro­furans, see: Holla et al. (1986 [triangle], 1987 [triangle], 1992 [triangle]). For the preparation of the title compound, see: Rai et al. (2008 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]). For hydrogen-bond motifs, see: Bernstein et al. (1995 [triangle]). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 [triangle]).

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Object name is e-66-o3031-scheme1.jpg

Experimental

Crystal data

  • C13H7NO4
  • M r = 241.20
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o3031-efi1.jpg
  • a = 10.4685 (2) Å
  • b = 7.3006 (1) Å
  • c = 15.2642 (2) Å
  • β = 110.867 (1)°
  • V = 1090.07 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.11 mm−1
  • T = 100 K
  • 0.47 × 0.38 × 0.28 mm

Data collection

  • Bruker SMART APEXII CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2009 [triangle]) T min = 0.950, T max = 0.970
  • 40673 measured reflections
  • 5796 independent reflections
  • 4934 reflections with I > 2σ(I)
  • R int = 0.030

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.119
  • S = 1.04
  • 5796 reflections
  • 163 parameters
  • H-atom parameters constrained
  • Δρmax = 0.59 e Å−3
  • Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2009 [triangle]); cell refinement: SAINT (Bruker, 2009 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810043850/fj2357sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810043850/fj2357Isup2.hkl

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

Acknowledgments

The authors express their thanks to Universiti Sains Malysia (USM) for providing research facilities. HKF and CKQ thank USM for a Research University Grant (No. 1001/PFIZIK/811160). CKQ also thanks USM for the award of a USM fellowship.

supplementary crystallographic information

Comment

Nitrofurans are class of synthetic compounds characterized by the presence of 5-nitro-2-furyl group. The presence of nitro group in the 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 activity (Holla et al., 1992; Holla et al., 1987). 1-Aryl-3-(5-nitro-2-furyl)-2-propyn-1-ones were prepared by the hydrobromination of 2,3-dibromo-1-aryl-3-(5-nitro-2-furyl)-2-propan-1-ones in the presence of triethylamine in benzene medium. The dibromopropanones were in turn obtained by the bromination of 1-aryl-3-(5-nitro-2-furyl)-2-propen-1-ones. Acid catalysed condensation of acetophenones with 5- nitrofuraldiacetate in acetic acid yielded the required 1-aryl-3-(5-nitro-2-furyl)-2-propen-1-ones called chalcones (Rai et al., 2008).

In the title molecule (Fig. 1), the 2-furyl (O1/C1–C4) ring is essentially planar (maximum deviation = 0.004 (1) Å for atoms O1) and is inclined at an angle of 11.69 (4)° with the phenyl ring (C11–C16), which indicates they are nearly parallel to each other. The nitro group (N1/O1/O2) is slightly twisted away from the attached 2-furyl ring [dihedral angle = 5.72 (8)]. There is a short O4···C1 contact (symmetry code : -x, -y, 2 - z) with distance = 2.8562 (8) Å which is shorter than the sum of van der Waals radii of the O and C atoms. Bond lengths (Allen et al., 1987) and angles are within normal ranges.

In the crystal packing (Fig. 2), the molecules are linked via a pair of intermolecular C2—H2···O2 hydrogen bonds, displaying R22(10) ring motifs (Bernstein et al., 1995). The molecules are further linked into two-dimensional networks parallel to (100) via intermolecular C11—H11···O4 hydrogen bonds. The crystal structure is further consilidated by C3—H3···Cg1 (Table 1), where Cg1 is the centroid of C8–C13 phenyl ring.

Experimental

To a stirred solution of 2,3-dibromo-3-(5-nitro-2-furyl)-1-phenylpropan-1-one (0.01 mol) in dry benzene (100 ml), a solution of triethylamine (0.04 mol) in dry benzene (30 ml) was added. The reaction mixture was stirred at room temperature for 24 h. The resulting mass of triethylamine hydrobromide was removed by filtration and the filtrate was concentrated by distilling the benzene under reduced pressure. The concentrated solution was cooled to room temperature. The product formed was collected by filtration and washed with ethanol. 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.

Refinement

All H atoms were positioned geometrically and refined using a riding model with C—H = 0.93 Å and Uiso(H) = 1.2Ueq(C). The highest residual electron density peak is located at 0.70 Å from C13 and the deepest hole is located at 1.10 Å from C1.

Figures

Fig. 1.
The molecular structure of the title compound showing 50% probability displacement ellipsoids for non-H atoms and the atom-numbering scheme.
Fig. 2.
The crystal structure of the title compound, viewed along the a axis. H atoms not involved in hydrogen bonds (dashed lines) have been omitted for clarity.

Crystal data

C13H7NO4F(000) = 496
Mr = 241.20Dx = 1.470 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 9876 reflections
a = 10.4685 (2) Åθ = 2.8–37.6°
b = 7.3006 (1) ŵ = 0.11 mm1
c = 15.2642 (2) ÅT = 100 K
β = 110.867 (1)°Block, brown
V = 1090.07 (3) Å30.47 × 0.38 × 0.28 mm
Z = 4

Data collection

Bruker SMART APEXII CCD area-detector diffractometer5796 independent reflections
Radiation source: fine-focus sealed tube4934 reflections with I > 2σ(I)
graphiteRint = 0.030
[var phi] and ω scansθmax = 37.7°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −17→17
Tmin = 0.950, Tmax = 0.970k = −12→12
40673 measured reflectionsl = −25→26

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0678P)2 + 0.1893P] where P = (Fo2 + 2Fc2)/3
5796 reflections(Δ/σ)max = 0.002
163 parametersΔρmax = 0.59 e Å3
0 restraintsΔρmin = −0.33 e Å3

Special details

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
O1−0.11630 (5)0.27415 (7)1.04906 (3)0.01471 (9)
O2−0.39290 (6)0.35131 (8)1.11730 (4)0.02350 (11)
O3−0.19217 (6)0.23310 (8)1.19322 (4)0.02173 (10)
O40.31281 (5)0.03921 (7)0.98678 (3)0.01702 (9)
N1−0.27662 (6)0.30540 (8)1.12394 (4)0.01630 (10)
C1−0.23941 (6)0.33853 (8)1.04384 (4)0.01429 (10)
C2−0.31207 (6)0.41459 (9)0.95952 (5)0.01643 (11)
H2−0.39840.46750.94120.020*
C3−0.22679 (6)0.39527 (9)0.90560 (5)0.01704 (11)
H3−0.24630.43350.84410.020*
C4−0.11011 (6)0.30936 (9)0.96198 (4)0.01464 (10)
C50.00843 (6)0.25151 (9)0.94661 (5)0.01623 (11)
C60.10953 (6)0.20010 (9)0.93282 (4)0.01633 (11)
C70.23677 (6)0.13782 (8)0.92494 (4)0.01320 (10)
C80.27014 (6)0.19941 (8)0.84344 (4)0.01292 (10)
C90.17614 (7)0.29769 (9)0.76987 (4)0.01676 (11)
H90.08970.32400.77070.020*
C100.21317 (8)0.35576 (10)0.69539 (5)0.02011 (12)
H100.15140.42140.64630.024*
C110.34271 (8)0.31575 (10)0.69438 (5)0.02020 (12)
H110.36730.35590.64480.024*
C120.43585 (7)0.21588 (10)0.76724 (5)0.01871 (11)
H120.52190.18860.76580.022*
C130.39983 (6)0.15728 (9)0.84181 (4)0.01523 (10)
H130.46150.09040.89040.018*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.01147 (17)0.01760 (19)0.01634 (19)0.00183 (14)0.00653 (14)0.00090 (15)
O20.0173 (2)0.0286 (3)0.0299 (3)0.00376 (18)0.0150 (2)−0.0001 (2)
O30.0219 (2)0.0261 (2)0.0180 (2)0.00245 (18)0.00804 (18)0.00227 (18)
O40.0181 (2)0.0185 (2)0.01441 (18)0.00230 (15)0.00568 (15)0.00193 (15)
N10.0158 (2)0.0164 (2)0.0192 (2)0.00019 (17)0.00932 (18)−0.00110 (17)
C10.0117 (2)0.0154 (2)0.0176 (2)0.00109 (17)0.00733 (18)−0.00024 (18)
C20.0131 (2)0.0173 (2)0.0191 (2)0.00249 (18)0.00597 (19)0.00072 (19)
C30.0155 (2)0.0189 (3)0.0172 (2)0.00230 (19)0.00642 (19)0.00149 (19)
C40.0132 (2)0.0159 (2)0.0166 (2)0.00058 (17)0.00742 (18)−0.00012 (18)
C50.0143 (2)0.0174 (2)0.0190 (2)−0.00023 (18)0.0085 (2)−0.00129 (19)
C60.0148 (2)0.0186 (3)0.0177 (2)0.00069 (19)0.00826 (19)−0.00003 (19)
C70.0124 (2)0.0142 (2)0.0139 (2)−0.00032 (16)0.00575 (17)−0.00142 (17)
C80.0122 (2)0.0142 (2)0.0128 (2)0.00024 (16)0.00488 (17)0.00001 (16)
C90.0150 (2)0.0180 (2)0.0157 (2)0.00193 (19)0.00354 (19)0.00166 (19)
C100.0241 (3)0.0193 (3)0.0146 (2)−0.0002 (2)0.0040 (2)0.0030 (2)
C110.0263 (3)0.0213 (3)0.0146 (2)−0.0062 (2)0.0092 (2)−0.0006 (2)
C120.0179 (3)0.0233 (3)0.0179 (2)−0.0032 (2)0.0100 (2)−0.0016 (2)
C130.0126 (2)0.0190 (2)0.0150 (2)0.00056 (18)0.00601 (18)0.00020 (18)

Geometric parameters (Å, °)

O1—C11.3472 (7)C6—C71.4525 (8)
O1—C41.3779 (8)C7—C81.4770 (8)
O2—N11.2315 (7)C8—C91.3990 (8)
O3—N11.2298 (8)C8—C131.4010 (8)
O4—C71.2278 (8)C9—C101.3915 (9)
N1—C11.4298 (8)C9—H90.9300
C1—C21.3586 (9)C10—C111.3927 (11)
C2—C31.4205 (9)C10—H100.9300
C2—H20.9300C11—C121.3953 (10)
C3—C41.3701 (9)C11—H110.9300
C3—H30.9300C12—C131.3880 (9)
C4—C51.4073 (8)C12—H120.9300
C5—C61.2100 (8)C13—H130.9300
C1—O1—C4104.51 (5)C6—C7—C8118.26 (5)
O3—N1—O2125.05 (6)C9—C8—C13120.49 (5)
O3—N1—C1118.47 (5)C9—C8—C7121.50 (5)
O2—N1—C1116.48 (6)C13—C8—C7118.01 (5)
O1—C1—C2113.56 (5)C10—C9—C8119.41 (6)
O1—C1—N1115.88 (5)C10—C9—H9120.3
C2—C1—N1130.40 (5)C8—C9—H9120.3
C1—C2—C3104.66 (5)C9—C10—C11120.06 (6)
C1—C2—H2127.7C9—C10—H10120.0
C3—C2—H2127.7C11—C10—H10120.0
C4—C3—C2106.57 (6)C10—C11—C12120.49 (6)
C4—C3—H3126.7C10—C11—H11119.8
C2—C3—H3126.7C12—C11—H11119.8
C3—C4—O1110.71 (5)C13—C12—C11119.86 (6)
C3—C4—C5132.41 (6)C13—C12—H12120.1
O1—C4—C5116.88 (5)C11—C12—H12120.1
C6—C5—C4179.25 (7)C12—C13—C8119.67 (6)
C5—C6—C7175.08 (7)C12—C13—H13120.2
O4—C7—C6118.85 (5)C8—C13—H13120.2
O4—C7—C8122.88 (5)
C4—O1—C1—C2−0.69 (7)O4—C7—C8—C9174.06 (6)
C4—O1—C1—N1175.17 (5)C6—C7—C8—C9−7.19 (9)
O3—N1—C1—O14.75 (9)O4—C7—C8—C13−6.23 (9)
O2—N1—C1—O1−174.73 (6)C6—C7—C8—C13172.52 (6)
O3—N1—C1—C2179.76 (7)C13—C8—C9—C10−0.90 (10)
O2—N1—C1—C20.28 (11)C7—C8—C9—C10178.80 (6)
O1—C1—C2—C30.46 (8)C8—C9—C10—C110.11 (10)
N1—C1—C2—C3−174.65 (7)C9—C10—C11—C120.64 (11)
C1—C2—C3—C4−0.02 (7)C10—C11—C12—C13−0.61 (11)
C2—C3—C4—O1−0.40 (7)C11—C12—C13—C8−0.18 (10)
C2—C3—C4—C5178.65 (7)C9—C8—C13—C120.93 (10)
C1—O1—C4—C30.65 (7)C7—C8—C13—C12−178.78 (6)
C1—O1—C4—C5−178.56 (6)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2···O2i0.932.443.3548 (9)170
C11—H11···O4ii0.932.403.2487 (9)152
C3—H3···Cg1iii0.932.863.6284 (7)141

Symmetry codes: (i) −x−1, −y+1, −z+2; (ii) x, −y+1/2, z−1/2; (iii) −x, y+1/2, −z+3/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: FJ2357).

References

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  • Cosier, J. & Glazer, A. M. (1986). J. Appl. Cryst.19, 105–107.
  • Holla, B. S., Kalluraya, B. & Shridhar, K. R. (1986). Curr. Sci.55, 73–76.
  • Holla, B. S., Kalluraya, B. & Shridhar, K. R. (1987). Curr. Sci.56, 236–238.
  • Holla, B. S., Kalluraya, B. & Shridhar, K. R. (1992). Rev. Roum. Chim.37, 1159–1164.
  • Rai, N. S., Kalluraya, B., Lingappa, B., Shenoy, S. & Puranic, V. G. (2008). Eur. J. Med. Chem.43, 1715–1720. [PubMed]
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
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