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Acta Crystallogr Sect E Struct Rep Online. 2010 February 1; 66(Pt 2): o466.
Published online 2010 January 30. doi:  10.1107/S1600536810003004
PMCID: PMC2979897

1-(1-Benzofuran-2-yl)-3-(4-chloro­phen­yl)prop-2-en-1-one

Abstract

In the title compound, C17H11ClO2, the benzofuran ring system is almost planar (r.m.s. deviation = 0.011 Å) and forms a dihedral angle of 10.53 (6)° with the chloro­phenyl ring. No significant inter­molecular inter­actions are observed.

Related literature

For general background to chalcone, see: Dhar (1981 [triangle]). For the biological properties of benzofuran derivatives, see: Nasef et al. (1992 [triangle]); Bogolyubsakaya & Perovich (1964 [triangle]); Deshmukh et al. (2004 [triangle]); Stanislav et al. (2000 [triangle]); Brady et al. (1973 [triangle]); Kamal et al. (2006 [triangle]); Alejandro et al. (2008 [triangle]); Rajesh et al. (2006 [triangle]). For related structures, see: Devarajegowda et al. (2001 [triangle]); Kant et al. (2009 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-0o466-scheme1.jpg

Experimental

Crystal data

  • C17H11ClO2
  • M r = 282.71
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o466-efi1.jpg
  • a = 15.9034 (12) Å
  • b = 14.1393 (12) Å
  • c = 5.9572 (5) Å
  • β = 93.039 (4)°
  • V = 1337.67 (19) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.28 mm−1
  • T = 293 K
  • 0.22 × 0.20 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.940, T max = 0.972
  • 12871 measured reflections
  • 3323 independent reflections
  • 2665 reflections with I > 2σ(I)
  • R int = 0.026

Refinement

  • R[F 2 > 2σ(F 2)] = 0.040
  • wR(F 2) = 0.115
  • S = 1.02
  • 3323 reflections
  • 182 parameters
  • H-atom parameters constrained
  • Δρmax = 0.21 e Å−3
  • Δρmin = −0.24 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [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: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97.

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003004/ci5024sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810003004/ci5024Isup2.hkl

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

Acknowledgments

The authors thank Professor T. N. Guru Row and Miss Brinda Selvaraj, Solid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore, for their help with the data collection.

supplementary crystallographic information

Comment

Chalcones have been recognized as a significant field of study for a long time because of a variety of biological activities as well as they serve as intermediates in the synthesis of a variety of heterocyclic compounds. Several heterocyclic analogues of chalcones have been reported to possess antibacterial, bacteriostatic tuberculostatic, insecticidal, antiparasitic, coronary vasodilating and choleretic activities (Dhar, 1981). Further, benzofuran derivatives have been reported to possess sedative and hypnotic (Nasef et al., 1992), antiinflammatory (Bogolyubsakaya & Perovich, 1964), antidepressant (Deshmukh et al., 2004), analgesic (Stanislav et al., 2000), hypoglycemic (Brady et al., 1973), anticonvulsant (Kamal et al., 2006), antibacterial (Alejandro et al., 2008) and antifungal activities (Rajesh et al., 2006). Owing to these biological activities of benzofuran propenones and in an attempt to study the structure-activity relationship of benzofuran and related systems, it was contemplated to synthesize benzofuryl propenones and the crystal structure of one of them, the title compound, is reported.

The benzofuran ring system is almost planar (r.m.s. deviation 0.011 Å). The dihedral angle between the benzofuran ring system and the chlorophenyl ring is 10.53 (6)°. Bond distances within the aromatic rings are in agreement with those observed in related structures (Devarajegowda et al., 2001; Kant et al., 2009).

Experimental

A mixture of 2-acetylbenzofuran (0.01 mol) and p-chlorobenzaldehyde (0.01 mol) in ethanol (20 ml) was stirred for 24 h in aqueous NaOH (8 ml). It was then diluted with water (100 ml) and acidified with concentrated HCl. The course of the reaction was monitored by TLC using chloroform-carbon disulfide (1:1). The product obtained was filtered, washed with water and recrystallised from ethanol (m.p. 398 K). Spectral data IR (KBr) cm-1: 1650 (C═O), 1620 (C═C stretching in aromatic), 1080 (C-O-C of benzofuran). 1H NMR (CDCl3): 6.67-7.2 (m, 9H, Ar-H), 6.70 (d, 1H, -COCH=), 8.60 (d, 1H, =CH-Ar).

Refinement

H atoms were positioned at calculated positions [C-H = 0.93 Å] and refined using a riding model with Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level.

Crystal data

C17H11ClO2F(000) = 584
Mr = 282.71Dx = 1.404 Mg m3
Monoclinic, P21/cMelting point: 398 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 15.9034 (12) ÅCell parameters from 3323 reflections
b = 14.1393 (12) Åθ = 1.3–28.4°
c = 5.9572 (5) ŵ = 0.28 mm1
β = 93.039 (4)°T = 293 K
V = 1337.67 (19) Å3Plate, white
Z = 40.22 × 0.20 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer3323 independent reflections
Radiation source: fine-focus sealed tube2665 reflections with I > 2σ(I)
graphiteRint = 0.026
ω and [var phi] scansθmax = 28.4°, θmin = 1.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)h = −21→20
Tmin = 0.940, Tmax = 0.972k = −18→18
12871 measured reflectionsl = −7→7

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040H-atom parameters constrained
wR(F2) = 0.115w = 1/[σ2(Fo2) + (0.0527P)2 + 0.3221P] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3323 reflectionsΔρmax = 0.21 e Å3
182 parametersΔρmin = −0.24 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0117 (16)

Special details

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
C11.22464 (9)0.64723 (11)0.5466 (3)0.0508 (4)
H11.19090.66710.42320.061*
C21.31402 (10)0.64001 (11)0.5583 (2)0.0497 (3)
C31.37837 (12)0.65858 (13)0.4117 (3)0.0628 (4)
H31.36600.68200.26790.075*
C41.45972 (12)0.64125 (15)0.4865 (3)0.0717 (5)
H41.50310.65350.39200.086*
C51.47890 (11)0.60577 (15)0.7004 (3)0.0692 (5)
H51.53490.59390.74470.083*
C61.41797 (10)0.58781 (13)0.8476 (3)0.0595 (4)
H61.43110.56440.99110.071*
C71.33559 (9)0.60625 (11)0.7727 (2)0.0485 (3)
C81.19823 (9)0.62016 (11)0.7456 (3)0.0517 (4)
C91.11355 (10)0.61170 (12)0.8310 (3)0.0540 (4)
C101.04368 (10)0.62421 (13)0.6625 (3)0.0560 (4)
H101.05460.65080.52420.067*
C110.96572 (9)0.59891 (11)0.7013 (3)0.0493 (3)
H110.95720.57190.84070.059*
C120.89149 (8)0.60906 (10)0.5471 (2)0.0440 (3)
C130.81273 (9)0.58296 (11)0.6193 (2)0.0480 (3)
H130.80900.55490.75960.058*
C140.74015 (9)0.59803 (11)0.4862 (3)0.0501 (3)
H140.68790.58120.53680.060*
C150.74645 (9)0.63839 (11)0.2773 (2)0.0473 (3)
C160.82376 (9)0.66272 (11)0.1978 (2)0.0493 (3)
H160.82710.68880.05530.059*
C170.89576 (9)0.64786 (11)0.3322 (2)0.0489 (3)
H170.94790.66380.27920.059*
O11.26490 (6)0.59456 (8)0.89122 (17)0.0552 (3)
O21.10294 (8)0.59470 (11)1.0286 (2)0.0755 (4)
Cl10.65624 (3)0.66004 (4)0.10847 (8)0.06940 (17)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0515 (8)0.0488 (8)0.0506 (8)0.0031 (6)−0.0110 (6)0.0007 (6)
C20.0542 (8)0.0455 (8)0.0481 (8)0.0008 (6)−0.0081 (6)−0.0025 (6)
C30.0775 (11)0.0621 (10)0.0489 (8)0.0026 (8)0.0042 (8)0.0027 (7)
C40.0633 (11)0.0824 (13)0.0706 (11)−0.0021 (9)0.0149 (9)−0.0053 (10)
C50.0491 (8)0.0854 (13)0.0723 (11)0.0035 (8)−0.0041 (8)−0.0112 (10)
C60.0537 (8)0.0719 (11)0.0515 (8)0.0067 (8)−0.0108 (7)−0.0022 (8)
C70.0486 (7)0.0495 (8)0.0466 (7)−0.0014 (6)−0.0050 (6)−0.0008 (6)
C80.0480 (7)0.0488 (8)0.0567 (8)0.0013 (6)−0.0114 (6)−0.0001 (7)
C90.0519 (8)0.0550 (9)0.0541 (9)−0.0010 (7)−0.0061 (6)0.0060 (7)
C100.0483 (8)0.0646 (10)0.0544 (9)0.0013 (7)−0.0038 (6)0.0095 (7)
C110.0496 (7)0.0517 (8)0.0462 (7)0.0034 (6)−0.0015 (6)0.0019 (6)
C120.0445 (7)0.0425 (7)0.0450 (7)0.0025 (6)0.0014 (5)−0.0011 (6)
C130.0502 (7)0.0496 (8)0.0444 (7)−0.0016 (6)0.0041 (6)0.0045 (6)
C140.0442 (7)0.0533 (9)0.0530 (8)−0.0057 (6)0.0052 (6)0.0002 (7)
C150.0456 (7)0.0467 (8)0.0490 (7)−0.0011 (6)−0.0042 (6)−0.0034 (6)
C160.0529 (8)0.0536 (8)0.0414 (7)−0.0046 (6)0.0013 (6)0.0026 (6)
C170.0444 (7)0.0559 (9)0.0468 (7)−0.0025 (6)0.0061 (6)−0.0008 (6)
O10.0499 (6)0.0655 (7)0.0491 (6)0.0006 (5)−0.0073 (4)0.0076 (5)
O20.0602 (7)0.1083 (11)0.0573 (7)−0.0042 (7)−0.0050 (5)0.0175 (7)
Cl10.0526 (2)0.0844 (3)0.0690 (3)−0.00645 (19)−0.01679 (19)0.0098 (2)

Geometric parameters (Å, °)

C1—C81.335 (2)C9—C101.468 (2)
C1—C21.423 (2)C10—C111.323 (2)
C1—H10.93C10—H100.93
C2—C71.389 (2)C11—C121.4641 (19)
C2—C31.405 (2)C11—H110.93
C3—C41.368 (3)C12—C131.3954 (19)
C3—H30.93C12—C171.398 (2)
C4—C51.388 (3)C13—C141.382 (2)
C4—H40.93C13—H130.93
C5—C61.365 (3)C14—C151.377 (2)
C5—H50.93C14—H140.93
C6—C71.386 (2)C15—C161.384 (2)
C6—H60.93C15—Cl11.7352 (15)
C7—O11.3690 (18)C16—C171.378 (2)
C8—O11.3820 (17)C16—H160.93
C8—C91.469 (2)C17—H170.93
C9—O21.2216 (19)
C8—C1—C2107.24 (13)C10—C9—C8115.33 (14)
C8—C1—H1126.4C11—C10—C9122.03 (15)
C2—C1—H1126.4C11—C10—H10119.0
C7—C2—C3118.89 (14)C9—C10—H10119.0
C7—C2—C1105.49 (14)C10—C11—C12126.58 (15)
C3—C2—C1135.61 (15)C10—C11—H11116.7
C4—C3—C2118.14 (16)C12—C11—H11116.7
C4—C3—H3120.9C13—C12—C17118.30 (13)
C2—C3—H3120.9C13—C12—C11119.20 (13)
C3—C4—C5121.44 (17)C17—C12—C11122.45 (13)
C3—C4—H4119.3C14—C13—C12121.23 (13)
C5—C4—H4119.3C14—C13—H13119.4
C6—C5—C4121.88 (17)C12—C13—H13119.4
C6—C5—H5119.1C15—C14—C13118.93 (13)
C4—C5—H5119.1C15—C14—H14120.5
C5—C6—C7116.70 (16)C13—C14—H14120.5
C5—C6—H6121.7C14—C15—C16121.37 (13)
C7—C6—H6121.7C14—C15—Cl1119.95 (12)
O1—C7—C6126.81 (14)C16—C15—Cl1118.68 (11)
O1—C7—C2110.25 (12)C17—C16—C15119.29 (13)
C6—C7—C2122.94 (15)C17—C16—H16120.4
C1—C8—O1111.44 (14)C15—C16—H16120.4
C1—C8—C9131.92 (14)C16—C17—C12120.83 (13)
O1—C8—C9116.62 (14)C16—C17—H17119.6
O2—C9—C10122.98 (15)C12—C17—H17119.6
O2—C9—C8121.69 (14)C7—O1—C8105.57 (12)
C8—C1—C2—C70.86 (17)O2—C9—C10—C11−14.3 (3)
C8—C1—C2—C3−178.91 (18)C8—C9—C10—C11165.10 (16)
C7—C2—C3—C40.8 (2)C9—C10—C11—C12179.27 (15)
C1—C2—C3—C4−179.41 (18)C10—C11—C12—C13−176.76 (16)
C2—C3—C4—C50.4 (3)C10—C11—C12—C170.4 (3)
C3—C4—C5—C6−1.0 (3)C17—C12—C13—C14−2.4 (2)
C4—C5—C6—C70.4 (3)C11—C12—C13—C14174.96 (14)
C5—C6—C7—O1−179.32 (16)C12—C13—C14—C150.9 (2)
C5—C6—C7—C20.9 (3)C13—C14—C15—C160.9 (2)
C3—C2—C7—O1178.67 (14)C13—C14—C15—Cl1−178.88 (12)
C1—C2—C7—O1−1.15 (17)C14—C15—C16—C17−1.2 (2)
C3—C2—C7—C6−1.5 (2)Cl1—C15—C16—C17178.57 (12)
C1—C2—C7—C6178.64 (15)C15—C16—C17—C12−0.3 (2)
C2—C1—C8—O1−0.28 (18)C13—C12—C17—C162.0 (2)
C2—C1—C8—C9−179.04 (16)C11—C12—C17—C16−175.20 (14)
C1—C8—C9—O2−172.20 (18)C6—C7—O1—C8−178.80 (16)
O1—C8—C9—O29.1 (2)C2—C7—O1—C80.98 (16)
C1—C8—C9—C108.3 (3)C1—C8—O1—C7−0.42 (17)
O1—C8—C9—C10−170.36 (14)C9—C8—O1—C7178.55 (13)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5024).

References

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