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

Devarajegowda, H. C.

D’souza, Alphonsus

Jeyaseelan, S.

Venkatarama, G.

Vinduvahini, M.

English

PubMed

In the title compound, C17H11ClO2, the benzofuran ring system is almost planar (r.m.s. deviation = 0.011&amp;#8197;&amp;#197;) and forms a dihedral angle of 10.53&amp;#8197;(6)&amp;#176; with the chlorophenyl ring. No significant intermolecular interactions are observed

S. Jeyaseelan

H. C. Devarajegowda

G. Venkatarama

M. Vinduvahini

Alphonsus D'souza

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Acta Crystallographica Section E Structure Reports Online

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

In the title compound, C\sb 17H\sb 11ClO\sb 2, the benzofuran ring system is almost planar (r.m.s. deviation = 0.011Å) and forms a dihedral angle of 10.53(6)\circ with the chloro\-phenyl ring. No significant inter\-molecular inter\-actions are observed

D'souza, Alphonsus

University of Mysore - Digital Repository of Research, Innovation and Scholarship (ePrints@UoM)

1-(1-Benzofuran-2-yl)-3-(4-chloro-phenyl)prop-2-en-1-oneS. Jeyaseelan,a H. C. Devarajegowda,a* G. Venkatarama,aM. Vinduvahinib and Alphonsus D’souzacaDepartment of Physics, Yuvaraja’s College (Constituent College), University ofMysore, Mysore 570 005, Karnataka, India, bDepartment of Physics, Sri D. Devarajurs. First Grade College, Hunsur 571 105, Karnataka, India, and cDepartment ofChemistry, St. Philomena’s College, Mysore 570 015, Karnataka, IndiaCorrespondence e-mail: devarajegowda@yahoo.comReceived 22 January 2010; accepted 25 January 2010Key indicators: single-crystal X-ray study; T = 293 K; mean (C–C) = 0.002 A˚;R factor = 0.040; wR factor = 0.115; data-to-parameter ratio = 18.3.In the title compound, C17H11ClO2, the benzofuran ringsystem is almost planar (r.m.s. deviation = 0.011 A˚) and formsa dihedral angle of 10.53 (6) with the chlorophenyl ring. Nosignificant intermolecular interactions are observed.Related literatureFor general background to chalcone, see: Dhar (1981). For thebiological properties of benzofuran derivatives, see: Nasef etal. (1992); Bogolyubsakaya & Perovich (1964); Deshmukh etal. (2004); Stanislav et al. (2000); Brady et al. (1973); Kamal etal. (2006); Alejandro et al. (2008); Rajesh et al. (2006). Forrelated structures, see: Devarajegowda et al. (2001); Kant et al.(2009).ExperimentalCrystal dataC17H11ClO2Mr = 282.71Monoclinic, P21=ca = 15.9034 (12) A˚b = 14.1393 (12) A˚c = 5.9572 (5) A˚ = 93.039 (4)V = 1337.67 (19) A˚3Z = 4Mo K radiation = 0.28 mm1T = 293 K0.22  0.20  0.10 mmData collectionBruker SMART CCD area-detectordiffractometerAbsorption correction: multi-scan(SADABS; Sheldrick, 2004)Tmin = 0.940, Tmax = 0.97212871 measured reflections3323 independent reflections2665 reflections with I > 2(I)Rint = 0.026RefinementR[F 2 > 2(F 2)] = 0.040wR(F 2) = 0.115S = 1.023323 reflections182 parametersH-atom parameters constrainedmax = 0.21 e A˚3min = 0.24 e A˚3Data collection: SMART (Bruker, 2001); cell refinement: SAINT(Bruker, 2001); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:ORTEP-3 (Farrugia, 1997); software used to prepare material forpublication: SHELXL97.The authors thank Professor T. N. Guru Row and MissBrinda Selvaraj, Solid State and Structural Chemistry Unit,Indian Institute of Science, Bangalore, for their help with thedata collection.Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: CI5024).ReferencesAlejandro, U., Javier, E., Marcos, R. & Marcela, W. (2008). Molecules, 13,2385–2393.Bogolyubsakaya, L. T. & Perovich, M. (1964). Zh. Obshch. Khim. 34, 3119–3122.Brady, B., Kenndey, J. & Sullivan, W. (1973). Tetrahedron, 29, 359–362.Bruker (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.Deshmukh, M., Kharade, D. & Shirke, S. D. (2004).Monatsh. Chem. 125, 971–976.Devarajegowda, H. C., Sridhar, M. A., Shashidhara Prasad, J., Indira, J.,Sooryanarayanarao, B. & Prakash, P. K. (2001). Mol. Cryst. Liq. Cryst. 369,145–152.Dhar, D. N. (1981). In The Chemistry of Chalcones and Related Compounds.New York: John Wiley.Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.Kamal, M., Hassan, A., Eman, A., Mohey, E. & Hanan, A. (2006). Bioorg.Med. Chem. 14, 3672–3680.Kant, R., Kamni,, Narayana, B., Veena, K. & Yathirajan, H. S. (2009). ActaCryst. E65, o836.Nasef, A. M., El-Naem, S. I. & El-Shabrawy, O. A. (1992). Egypt. J. Pharm. Sci.34, 463–467.Rajesh, K., Rajendra, P., Mayur, Y., Shanta, K. & Raju, M. (2006). Indian J.Heterocycl. Chem. 15, 245–253.Sheldrick, G. M. (2004). SADABS. University of Go¨ttingen, Germany.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Stanislav, R., Petr, H., Petr, K. & Ivan, K. (2000). Collect. Czech. Chem.Commun. 65, 1093–1108.organic compoundso466 Jeyaseelan et al. doi:10.1107/S1600536810003004 Acta Cryst. (2010). E66, o466Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supporting informationsup-1Acta Cryst. (2010). E66, o466    supporting informationActa Cryst. (2010). E66, o466    [https://doi.org/10.1107/S1600536810003004]1-(1-Benzofuran-2-yl)-3-(4-chlorophenyl)prop-2-en-1-oneS. Jeyaseelan, H. C. Devarajegowda, G. Venkatarama, M. Vinduvahini and Alphonsus D'souzaS1. 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).S2. 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).S3. 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).supporting informationsup-2Acta Cryst. (2010). E66, o466    Figure 1The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. 1-(1-Benzofuran-2-yl)-3-(4-chlorophenyl)prop-2-en-1-one Crystal data C17H11ClO2Mr = 282.71Monoclinic, P21/cHall symbol: -P 2ybca = 15.9034 (12) Åb = 14.1393 (12) Åc = 5.9572 (5) Åβ = 93.039 (4)°V = 1337.67 (19) Å3Z = 4F(000) = 584Dx = 1.404 Mg m−3Melting point: 398 KMo Kα radiation, λ = 0.71073 ÅCell parameters from 3323 reflectionsθ = 1.3–28.4°µ = 0.28 mm−1T = 293 KPlate, white0.22 × 0.20 × 0.10 mmData collection Bruker SMART CCD area-detector diffractometerRadiation source: fine-focus sealed tubeGraphite monochromatorω and φ scansAbsorption correction: multi-scan (SADABS; Sheldrick, 2004)Tmin = 0.940, Tmax = 0.97212871 measured reflections3323 independent reflections2665 reflections with I > 2σ(I)Rint = 0.026θmax = 28.4°, θmin = 1.3°h = −21→20k = −18→18l = −7→7Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.040wR(F2) = 0.115S = 1.023323 reflections182 parameters0 restraintsPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapHydrogen site location: inferred from neighbouring sitesH-atom parameters constrainedw = 1/[σ2(Fo2) + (0.0527P)2 + 0.3221P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max = 0.001Δρmax = 0.21 e Å−3Δρmin = −0.24 e Å−3Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4Extinction coefficient: 0.0117 (16)supporting informationsup-3Acta Cryst. (2010). E66, o466    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) x y z Uiso*/UeqC1 1.22464 (9) 0.64723 (11) 0.5466 (3) 0.0508 (4)H1 1.1909 0.6671 0.4232 0.061*C2 1.31402 (10) 0.64001 (11) 0.5583 (2) 0.0497 (3)C3 1.37837 (12) 0.65858 (13) 0.4117 (3) 0.0628 (4)H3 1.3660 0.6820 0.2679 0.075*C4 1.45972 (12) 0.64125 (15) 0.4865 (3) 0.0717 (5)H4 1.5031 0.6535 0.3920 0.086*C5 1.47890 (11) 0.60577 (15) 0.7004 (3) 0.0692 (5)H5 1.5349 0.5939 0.7447 0.083*C6 1.41797 (10) 0.58781 (13) 0.8476 (3) 0.0595 (4)H6 1.4311 0.5644 0.9911 0.071*C7 1.33559 (9) 0.60625 (11) 0.7727 (2) 0.0485 (3)C8 1.19823 (9) 0.62016 (11) 0.7456 (3) 0.0517 (4)C9 1.11355 (10) 0.61170 (12) 0.8310 (3) 0.0540 (4)C10 1.04368 (10) 0.62421 (13) 0.6625 (3) 0.0560 (4)H10 1.0546 0.6508 0.5242 0.067*C11 0.96572 (9) 0.59891 (11) 0.7013 (3) 0.0493 (3)H11 0.9572 0.5719 0.8407 0.059*C12 0.89149 (8) 0.60906 (10) 0.5471 (2) 0.0440 (3)C13 0.81273 (9) 0.58296 (11) 0.6193 (2) 0.0480 (3)H13 0.8090 0.5549 0.7596 0.058*C14 0.74015 (9) 0.59803 (11) 0.4862 (3) 0.0501 (3)H14 0.6879 0.5812 0.5368 0.060*C15 0.74645 (9) 0.63839 (11) 0.2773 (2) 0.0473 (3)C16 0.82376 (9) 0.66272 (11) 0.1978 (2) 0.0493 (3)H16 0.8271 0.6888 0.0553 0.059*C17 0.89576 (9) 0.64786 (11) 0.3322 (2) 0.0489 (3)H17 0.9479 0.6638 0.2792 0.059*O1 1.26490 (6) 0.59456 (8) 0.89122 (17) 0.0552 (3)O2 1.10294 (8) 0.59470 (11) 1.0286 (2) 0.0755 (4)Cl1 0.65624 (3) 0.66004 (4) 0.10847 (8) 0.06940 (17)Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23C1 0.0515 (8) 0.0488 (8) 0.0506 (8) 0.0031 (6) −0.0110 (6) 0.0007 (6)supporting informationsup-4Acta Cryst. (2010). E66, o466    C2 0.0542 (8) 0.0455 (8) 0.0481 (8) 0.0008 (6) −0.0081 (6) −0.0025 (6)C3 0.0775 (11) 0.0621 (10) 0.0489 (8) 0.0026 (8) 0.0042 (8) 0.0027 (7)C4 0.0633 (11) 0.0824 (13) 0.0706 (11) −0.0021 (9) 0.0149 (9) −0.0053 (10)C5 0.0491 (8) 0.0854 (13) 0.0723 (11) 0.0035 (8) −0.0041 (8) −0.0112 (10)C6 0.0537 (8) 0.0719 (11) 0.0515 (8) 0.0067 (8) −0.0108 (7) −0.0022 (8)C7 0.0486 (7) 0.0495 (8) 0.0466 (7) −0.0014 (6) −0.0050 (6) −0.0008 (6)C8 0.0480 (7) 0.0488 (8) 0.0567 (8) 0.0013 (6) −0.0114 (6) −0.0001 (7)C9 0.0519 (8) 0.0550 (9) 0.0541 (9) −0.0010 (7) −0.0061 (6) 0.0060 (7)C10 0.0483 (8) 0.0646 (10) 0.0544 (9) 0.0013 (7) −0.0038 (6) 0.0095 (7)C11 0.0496 (7) 0.0517 (8) 0.0462 (7) 0.0034 (6) −0.0015 (6) 0.0019 (6)C12 0.0445 (7) 0.0425 (7) 0.0450 (7) 0.0025 (6) 0.0014 (5) −0.0011 (6)C13 0.0502 (7) 0.0496 (8) 0.0444 (7) −0.0016 (6) 0.0041 (6) 0.0045 (6)C14 0.0442 (7) 0.0533 (9) 0.0530 (8) −0.0057 (6) 0.0052 (6) 0.0002 (7)C15 0.0456 (7) 0.0467 (8) 0.0490 (7) −0.0011 (6) −0.0042 (6) −0.0034 (6)C16 0.0529 (8) 0.0536 (8) 0.0414 (7) −0.0046 (6) 0.0013 (6) 0.0026 (6)C17 0.0444 (7) 0.0559 (9) 0.0468 (7) −0.0025 (6) 0.0061 (6) −0.0008 (6)O1 0.0499 (6) 0.0655 (7) 0.0491 (6) 0.0006 (5) −0.0073 (4) 0.0076 (5)O2 0.0602 (7) 0.1083 (11) 0.0573 (7) −0.0042 (7) −0.0050 (5) 0.0175 (7)Cl1 0.0526 (2) 0.0844 (3) 0.0690 (3) −0.00645 (19) −0.01679 (19) 0.0098 (2)Geometric parameters (Å, º) C1—C8 1.335 (2) C9—C10 1.468 (2)C1—C2 1.423 (2) C10—C11 1.323 (2)C1—H1 0.93 C10—H10 0.93C2—C7 1.389 (2) C11—C12 1.4641 (19)C2—C3 1.405 (2) C11—H11 0.93C3—C4 1.368 (3) C12—C13 1.3954 (19)C3—H3 0.93 C12—C17 1.398 (2)C4—C5 1.388 (3) C13—C14 1.382 (2)C4—H4 0.93 C13—H13 0.93C5—C6 1.365 (3) C14—C15 1.377 (2)C5—H5 0.93 C14—H14 0.93C6—C7 1.386 (2) C15—C16 1.384 (2)C6—H6 0.93 C15—Cl1 1.7352 (15)C7—O1 1.3690 (18) C16—C17 1.378 (2)C8—O1 1.3820 (17) C16—H16 0.93C8—C9 1.469 (2) C17—H17 0.93C9—O2 1.2216 (19)C8—C1—C2 107.24 (13) C10—C9—C8 115.33 (14)C8—C1—H1 126.4 C11—C10—C9 122.03 (15)C2—C1—H1 126.4 C11—C10—H10 119.0C7—C2—C3 118.89 (14) C9—C10—H10 119.0C7—C2—C1 105.49 (14) C10—C11—C12 126.58 (15)C3—C2—C1 135.61 (15) C10—C11—H11 116.7C4—C3—C2 118.14 (16) C12—C11—H11 116.7C4—C3—H3 120.9 C13—C12—C17 118.30 (13)supporting informationsup-5Acta Cryst. (2010). E66, o466    C2—C3—H3 120.9 C13—C12—C11 119.20 (13)C3—C4—C5 121.44 (17) C17—C12—C11 122.45 (13)C3—C4—H4 119.3 C14—C13—C12 121.23 (13)C5—C4—H4 119.3 C14—C13—H13 119.4C6—C5—C4 121.88 (17) C12—C13—H13 119.4C6—C5—H5 119.1 C15—C14—C13 118.93 (13)C4—C5—H5 119.1 C15—C14—H14 120.5C5—C6—C7 116.70 (16) C13—C14—H14 120.5C5—C6—H6 121.7 C14—C15—C16 121.37 (13)C7—C6—H6 121.7 C14—C15—Cl1 119.95 (12)O1—C7—C6 126.81 (14) C16—C15—Cl1 118.68 (11)O1—C7—C2 110.25 (12) C17—C16—C15 119.29 (13)C6—C7—C2 122.94 (15) C17—C16—H16 120.4C1—C8—O1 111.44 (14) C15—C16—H16 120.4C1—C8—C9 131.92 (14) C16—C17—C12 120.83 (13)O1—C8—C9 116.62 (14) C16—C17—H17 119.6O2—C9—C10 122.98 (15) C12—C17—H17 119.6O2—C9—C8 121.69 (14) C7—O1—C8 105.57 (12)C8—C1—C2—C7 0.86 (17) O2—C9—C10—C11 −14.3 (3)C8—C1—C2—C3 −178.91 (18) C8—C9—C10—C11 165.10 (16)C7—C2—C3—C4 0.8 (2) C9—C10—C11—C12 179.27 (15)C1—C2—C3—C4 −179.41 (18) C10—C11—C12—C13 −176.76 (16)C2—C3—C4—C5 0.4 (3) C10—C11—C12—C17 0.4 (3)C3—C4—C5—C6 −1.0 (3) C17—C12—C13—C14 −2.4 (2)C4—C5—C6—C7 0.4 (3) C11—C12—C13—C14 174.96 (14)C5—C6—C7—O1 −179.32 (16) C12—C13—C14—C15 0.9 (2)C5—C6—C7—C2 0.9 (3) C13—C14—C15—C16 0.9 (2)C3—C2—C7—O1 178.67 (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—C17 178.57 (12)C1—C2—C7—C6 178.64 (15) C15—C16—C17—C12 −0.3 (2)C2—C1—C8—O1 −0.28 (18) C13—C12—C17—C16 2.0 (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—O2 9.1 (2) C2—C7—O1—C8 0.98 (16)C1—C8—C9—C10 8.3 (3) C1—C8—O1—C7 −0.42 (17)O1—C8—C9—C10 −170.36 (14) C9—C8—O1—C7 178.55 (13)

1-(1-Benzofuran-2-yl)-3-(4-chloro\-phen\-yl)prop-2-en-1-one

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/Ueq

organic compounds o466 Jeyaseelan et al. doi:10.1107/S1600536810003004 Acta Cryst.

http://eprints.uni-mysore.ac.in/5291/1/1-%281-Benzofuran-2-yl%29-3.pdf

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

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

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

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