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Acta Crystallogr Sect E Struct Rep Online. 2009 May 1; 65(Pt 5): o1087.
Published online 2009 April 22. doi:  10.1107/S1600536809014299
PMCID: PMC2977766

(E)-1-(4-Bromo­phen­yl)-3-(2-fur­yl)prop-2-en-1-one

Abstract

In the title compound, C13H9BrO2, the benzene and furan rings form a dihedral angle of 44.35 (14)°. The crystal packing exhibits no significantly short inter­molecular contacts.

Related literature

For the crystal structure of a related compound, see: Li et al. (1992 [triangle]). For general background, see: Yadav & Mashram (2001 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o1087-scheme1.jpg

Experimental

Crystal data

  • C13H9BrO2
  • M r = 277.11
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o1087-efi1.jpg
  • a = 14.172 (4) Å
  • b = 14.064 (4) Å
  • c = 5.8002 (18) Å
  • β = 98.353 (4)°
  • V = 1143.8 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 3.57 mm−1
  • T = 298 K
  • 0.48 × 0.40 × 0.34 mm

Data collection

  • Bruker SMART APEX CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.279, T max = 0.376 (expected range = 0.220–0.297)
  • 5665 measured reflections
  • 2015 independent reflections
  • 1344 reflections with I > 2σ(I)
  • R int = 0.028

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.133
  • S = 1.07
  • 2015 reflections
  • 145 parameters
  • H-atom parameters constrained
  • Δρmax = 0.35 e Å−3
  • Δρmin = −0.45 e Å−3

Data collection: SMART (Siemens, 1996 [triangle]); cell refinement: SAINT (Siemens, 1996 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014299/cv2540sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014299/cv2540Isup2.hkl

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

Acknowledgments

This project was supported by the Foundation of Linyi Normal University (grant No. LY0801).

supplementary crystallographic information

Comment

Reactions under solvent-free or so-called dry media conditions are especially appealing as they provide an opportunity to work with open vessels, thus avoiding the risk of high pressure development and with the possibility of upscaling the reactions to larger scale (Yadav & Mashram, 2001).

In continuation of our ongoing program directed to the development of environmentally benign methods of chemical synthesis, we describe in this paper a user-friendly, solvent-free protocol for the synthesis of chalcones starting from the fragrant aldehydes and fragrant ketones in the presence of NaOH under solvent-free conditions. Using this method, which can be considered as a a general method for the synthesis of chalcones, we obtained the title compound, (I). We present here its crystal structure.

In (I) (Fig. 1), the bond lengths and angles are normal and comparable to those observed in the reported compound (Li et al., 1992). The benzene and furan rings form a dihedral angle of 44.35 (14)°. The crystal packing exhibits no significantly short intermolecular contacts.

Experimental

Furan-2-carbaldehyde (0.5 mmol) and 4-bromoacetophenone (0.5 mmol), NaOH (0.5 mmol) were mixed in 50 ml flash under sovlent-free condtions. After stirring for 5 min at 293 K, the resulting mixture was washed with water for several times for removing NaOH, and recrystallized from ethanol, and afforded the title compound as a crystalline solid. Elemental analysis: calculated for C13H9BrO2: C 56.34, H 3.27%; found: C 56.38, H 3.35%.

Refinement

All H atoms were placed in geometrically idealized positions (C—H 0.93 Å) and treated as riding on their parent atoms, with Uiso(H) = 1.2 Ueq(C).

Figures

Fig. 1.
The molecular structure of (I) showing the atomic numbering scheme and 30% probability displacement ellipsoids.

Crystal data

C13H9BrO2F(000) = 552
Mr = 277.11Dx = 1.609 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 14.172 (4) ÅCell parameters from 1645 reflections
b = 14.064 (4) Åθ = 2.9–24.0°
c = 5.8002 (18) ŵ = 3.57 mm1
β = 98.353 (4)°T = 298 K
V = 1143.8 (6) Å3Block, yellow
Z = 40.48 × 0.40 × 0.34 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer2015 independent reflections
Radiation source: fine-focus sealed tube1344 reflections with I > 2σ(I)
graphiteRint = 0.028
[var phi] and ω scansθmax = 25.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −16→16
Tmin = 0.279, Tmax = 0.376k = −16→16
5665 measured reflectionsl = −4→6

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0633P)2 + 0.7234P] where P = (Fo2 + 2Fc2)/3
2015 reflections(Δ/σ)max < 0.001
145 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = −0.45 e Å3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Br1−0.41996 (3)0.37809 (5)0.12851 (11)0.0898 (3)
O10.0212 (2)0.3772 (2)−0.1992 (5)0.0770 (10)
O20.2477 (3)0.3452 (3)0.5655 (7)0.0839 (10)
C10.0029 (3)0.3749 (3)−0.0007 (7)0.0524 (10)
C20.0790 (3)0.3714 (3)0.2017 (8)0.0542 (11)
H20.06370.35770.34870.065*
C30.1694 (3)0.3878 (3)0.1760 (8)0.0558 (11)
H30.18110.40540.02820.067*
C40.2501 (4)0.3809 (3)0.3540 (8)0.0609 (12)
C50.3401 (3)0.4042 (3)0.3343 (8)0.0566 (12)
H50.36120.42980.20320.068*
C60.3966 (3)0.3830 (4)0.5455 (10)0.0765 (15)
H60.46200.39280.58100.092*
C70.3415 (4)0.3471 (4)0.6837 (9)0.0754 (14)
H70.36090.32630.83530.091*
C8−0.0983 (3)0.3758 (3)0.0412 (7)0.0450 (9)
C9−0.1271 (3)0.4102 (3)0.2437 (7)0.0505 (10)
H9−0.08170.43140.36460.061*
C10−0.2221 (3)0.4132 (3)0.2679 (8)0.0550 (11)
H10−0.24110.43730.40320.066*
C11−0.2888 (3)0.3802 (3)0.0900 (8)0.0524 (10)
C12−0.2635 (3)0.3453 (3)−0.1120 (8)0.0581 (11)
H12−0.30960.3227−0.22980.070*
C13−0.1670 (3)0.3443 (3)−0.1383 (7)0.0527 (10)
H13−0.14870.3225−0.27650.063*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Br10.0493 (3)0.1156 (6)0.1045 (5)0.0100 (3)0.0115 (3)−0.0091 (4)
O10.065 (2)0.120 (3)0.0475 (19)0.000 (2)0.0141 (16)0.0032 (18)
O20.075 (2)0.091 (3)0.085 (3)−0.0059 (19)0.005 (2)0.001 (2)
C10.058 (2)0.057 (3)0.043 (2)0.002 (2)0.0087 (19)0.002 (2)
C20.057 (3)0.056 (3)0.052 (2)0.0015 (19)0.013 (2)0.004 (2)
C30.057 (3)0.063 (3)0.049 (2)0.010 (2)0.014 (2)0.004 (2)
C40.069 (3)0.061 (3)0.052 (3)0.016 (2)0.006 (2)0.000 (2)
C50.043 (2)0.081 (3)0.049 (2)0.006 (2)0.019 (2)0.012 (2)
C60.046 (3)0.091 (4)0.093 (4)−0.003 (3)0.015 (3)−0.008 (3)
C70.075 (3)0.086 (4)0.062 (3)0.006 (3)−0.005 (3)0.001 (3)
C80.049 (2)0.044 (2)0.043 (2)0.0012 (18)0.0058 (18)0.0046 (18)
C90.056 (3)0.055 (2)0.039 (2)−0.0066 (19)0.0008 (19)−0.0005 (18)
C100.060 (3)0.059 (3)0.046 (2)0.008 (2)0.009 (2)−0.003 (2)
C110.046 (2)0.052 (2)0.059 (3)0.0096 (19)0.006 (2)0.000 (2)
C120.054 (3)0.061 (3)0.056 (3)0.004 (2)−0.005 (2)−0.004 (2)
C130.067 (3)0.051 (2)0.040 (2)0.008 (2)0.007 (2)−0.0048 (19)

Geometric parameters (Å, °)

Br1—C111.905 (4)C6—C71.300 (7)
O1—C11.217 (5)C6—H60.9300
O2—C41.331 (6)C7—H70.9300
O2—C71.405 (6)C8—C91.385 (6)
C1—C21.475 (6)C8—C131.391 (6)
C1—C81.489 (6)C9—C101.374 (6)
C2—C31.331 (6)C9—H90.9300
C2—H20.9300C10—C111.374 (6)
C3—C41.428 (7)C10—H100.9300
C3—H30.9300C11—C121.365 (6)
C4—C51.337 (6)C12—C131.398 (6)
C5—C61.395 (7)C12—H120.9300
C5—H50.9300C13—H130.9300
C4—O2—C7107.1 (4)C6—C7—H7125.7
O1—C1—C2121.4 (4)O2—C7—H7125.7
O1—C1—C8119.8 (4)C9—C8—C13119.0 (4)
C2—C1—C8118.7 (4)C9—C8—C1123.4 (4)
C3—C2—C1120.6 (4)C13—C8—C1117.5 (4)
C3—C2—H2119.7C10—C9—C8120.7 (4)
C1—C2—H2119.7C10—C9—H9119.6
C2—C3—C4126.2 (4)C8—C9—H9119.6
C2—C3—H3116.9C9—C10—C11119.3 (4)
C4—C3—H3116.9C9—C10—H10120.3
O2—C4—C5108.9 (4)C11—C10—H10120.4
O2—C4—C3124.5 (4)C12—C11—C10121.9 (4)
C5—C4—C3126.5 (4)C12—C11—Br1118.5 (3)
C4—C5—C6107.9 (4)C10—C11—Br1119.5 (3)
C4—C5—H5126.1C11—C12—C13118.7 (4)
C6—C5—H5126.1C11—C12—H12120.7
C7—C6—C5107.7 (4)C13—C12—H12120.7
C7—C6—H6126.2C8—C13—C12120.3 (4)
C5—C6—H6126.2C8—C13—H13119.8
C6—C7—O2108.5 (5)C12—C13—H13119.8

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CV2540).

References

  • Li, Z.-D., Huang, L.-Z., Su, G.-B. & Wang, H.-Y. (1992). Chin. J. Struct. Chem.11, 1–4.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Siemens (1996). SMART and SAINT Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA.
  • Yadav, J. S. & Mashram, H. M. (2001). Pure. Appl. Chem.73, 199–203.

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