In the title compound, C19H13ClO, the benzene ring and the naphthalene system, are twisted by 12.3 (3) and 36.1 (2)°, respectively, and in opposite directions with respect to the central propenone bridge. The bond-angle pattern within the benzene ring is influence by both substituents; these influences are almost additive. In the crystal, the molecules are linked by C—H⋯O and C—H⋯Cl inter­actions

Dutkiewicz, Grzegorz

Kubicki, Maciej

Narayana, B.

Samshuddin, S.

Yathirajan, H. S.

Acta Crystallographica Section E

English

PubMed

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

(E)-3-(4-Chlorophenyl)-1-(1-naphthyl)-prop-2-en-1-oneGrzegorz Dutkiewicz,a S. Samshuddin,b B. Narayana,bH. S. Yathirajanc and Maciej Kubickia*aDepartment of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780Poznan´, Poland, bDepartment of Studies in Chemistry, Mangalore University,Mangalagangotri 574 199, India, and cDepartment of Studies in Chemistry,University of Mysore, Mysore 570 006, IndiaCorrespondence e-mail: mkubicki@amu.edu.plReceived 13 November 2009; accepted 24 November 2009Key indicators: single-crystal X-ray study; T = 295 K; mean (C–C) = 0.004 A˚;R factor = 0.035; wR factor = 0.083; data-to-parameter ratio = 9.8.In the title compound, C19H13ClO, the benzene ring and thenaphthalene system, are twisted by 12.3 (3) and 36.1 (2),respectively, and in opposite directions with respect to thecentral propenone bridge. The bond-angle pattern within thebenzene ring is influence by both substituents; these influencesare almost additive. In the crystal, the molecules are linked byC—H  O and C—H  Cl interactions.Related literatureFor chalcones, see: Dhar (1981); Di Carlo et al. (1999);Dimmock et al. (1999); Goto et al. (1991); Indira et al. (2002);Sarojini et al. (2006); Satyanarayana et al. (2004); Uchida et al.(1998); Yarishkin (2008). For the 1-naphtyl analogue, see:Eswaramoorthy et al. (1994). For the influence of substituentson the geometry of the phenyl ring, see: Domenicano (1988).For a description of the Cambridge Crystallographic Data-base, see: Allen (2002).ExperimentalCrystal dataC19H13ClOMr = 292.74Monoclinic, Pca = 12.0392 (14) A˚b = 8.0544 (5) A˚c = 7.8472 (6) A˚ = 98.091 (10)V = 753.36 (11) A˚3Z = 2Mo K radiation = 0.25 mm1T = 295 K0.30  0.20  0.15 mmData collectionOxford Diffraction Xcalibur(Sapphire2, large Be window)diffractometerAbsorption correction: multi-scan(CrysAlis PRO; OxfordDiffraction, 2009)Tmin = 0.666, Tmax = 1.0002481 measured reflections1866 independent reflections1440 reflections with I > 2(I)Rint = 0.014RefinementR[F 2 > 2(F 2)] = 0.035wR(F 2) = 0.083S = 0.961866 reflections190 parameters2 restraintsH-atom parameters constrainedmax = 0.12 e A˚3min = 0.13 e A˚3Absolute structure: Flack (1983),423 Friedel pairsFlack parameter: 0.08 (7)Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AC17—H17  O12i 0.93 2.42 3.180 (4) 139C3—H3  Cl21ii 0.93 2.92 3.703 (3) 143C8—H8  O12iii 0.93 2.64 3.546 (4) 163Symmetry codes: (i) x; y þ 1; z; (ii) x 1;yþ 2; z  12; (iii) x;y; z 12.Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cellrefinement: CrysAlis PRO; data reduction: CrysAlis PRO;program(s) used to solve structure: SIR92 (Altomare et al., 1993);program(s) used to refine structure: SHELXL97 (Sheldrick, 2008);molecular graphics: Stereochemical Workstation Operation Manual(Siemens, 1989); software used to prepare material for publication:SHELXL97.SS thanks Mangalore University for the research facilitie.Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: FK2008).ReferencesAllen, F. H. (2002). Acta Cryst. B58, 380–388.Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A (1993). J. Appl.Cryst. 26, 343–350.Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds. NewYork: John Wiley.Di Carlo, G., Mascolo, N., Izzo, A. A. & Capasso, F. (1999). Life Sci. 65, 337–353.Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr.Med. Chem. 6, 1125–1149.Domenicano, A. (1988). In Stereochemical Applications of gas-phase electrondiffraction, edited by I. Hargittai & M. Hargittai, pp. 281–324. New York:VCH.Eswaramoorthy, S., Ponnuswamy, M. N., Raju, K. S., Nanjundan, S. &Krishnasamy, V. (1994). Z. Kristallogr. 209, 669–672.Flack, H. D. (1983). Acta Cryst. A39, 876–881.Goto, Y., Hayashi, A., Kimura, Y. & Nakayama, M. (1991). J. Cryst. Growth,108, 688–698.Indira, J., Karat, P. P. & Sarojini, B. K. (2002). J. Cryst. Growth, 242, 209–214.Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton,Oxfordshire, England.Sarojini, B. K., Narayana, B., Ashalatha, B. V., Indira, J. & Lobo, K. G. (2006).J. Cryst. Growth, 295, 54–59.organic compoundsActa Cryst. (2009). E65, o3255–o3256 doi:10.1107/S1600536809050508 Dutkiewicz et al. o3255Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368Satyanarayana, M., Tiwari, P., Tripathi, B. K., Sriwastava, A. K. & Pratap, R.(2004). Bioorg. Med. Chem., 12, 883–889.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Siemens (1989). Stereochemical Workstation Operation Manual. SiemensAnalytical X-ray Instruments Inc., Madison, Wisconsin, USA.Uchida, T., Kozawa, K., Sakai, T., Aoki, M., Yoguchi, H., Abduryim, A. &Watanabe, Y. (1998). Mol. Cryst. Liq. Cryst. 315, 135–140.Yarishkin, O. V. (2008). Bioorg. Med. Chem. Lett. 18, 137–140.organic compoundso3256 Dutkiewicz et al.  C19H13ClO Acta Cryst. (2009). E65, o3255–o3256supporting informationsup-1Acta Cryst. (2009). E65, o3255–o3256    supporting informationActa Cryst. (2009). E65, o3255–o3256    [doi:10.1107/S1600536809050508](E)-3-(4-Chlorophenyl)-1-(1-naphthyl)prop-2-en-1-oneGrzegorz Dutkiewicz, S. Samshuddin, B. Narayana, H. S. Yathirajan and Maciej KubickiS1. Comment Chalcones constitute an important family of flavonoids. They have been reported to possess many interesting pharmacological activities (Dhar, 1981) including anti-inflammatory, antimicrobial, antifungal, antioxidant, cytotoxic, antitumor and anticancer activities (Dimmock et al., 1999; Satyanarayana et al., 2004). Some chalcones demonstrated the ability to block voltage-dependent potassium channels (Yarishkin et al., 2008). Chalcones are also finding application as organic nonlinear optical materials (NLO) for their SHG conversion efficiency (Sarojini et al., 2006). Chalcone derivatives are recognized material in the NLO applications because of their excellent blue light transmittance and good crystallization ability (Goto et al.,1991; Uchida et al.,1998; Indira et al., 2002). Chemically chalcones consists of open-chain flavonoids in which the two aromatic rings are joined by α,\&s-unsaturated carbonyl system. The radical quenching properties of the phenolic groups present in many chalcones have raised interest in using these compounds or chalcone rich plant extracts as drugs or food preservatives (Di Carlo et al., 1999). As a part of our efforts on the synthesis of naphthyl chalcones, this paper describes the crystal structure of a new naphthyl chalcone, (2E)-3-(4-Chloro-phenyl)-1-(naphthalen-1-yl)prop-2-en-1-one (I, Scheme 1). There are 298 structures in the Cambridge Crystallographic Database (Allen, 2002: Ver. 5.30, Nov. 2008, last update Sep. 2009) that posses two aromatic moieties connected via CH=CH—CO– fragment, but only 10 of them are naphthyl chalcones, and the single one example with 1-naphthalene substituent (1-(1-Naphthalenyl)-3-(4-nitrophenyl)-2-propenone, Eswaramoorthy et al., 1994). It might be noted, that this structure apparently has errors: one of the torsion angles in the aromatic ring is as large as 5°.The molecule of I is built of three approximately planar fragments (Fig. 1): the phenyl ring (A, maximum deviation form the least-squares plane is 0.006 (3) Å), propenone fragment C=C—C=O (B, 0.014 (2) Å), and the naphtalene ring system (C). This last fragment however is significantly folded, even though both individual rings are almost planar, the dihedral angle between these planes is as high as 5.05 (13)°. The overall conformation of I can be described in terms of dihedral angles between these fragments: A/B 36.1 (2)°, B/C 12.3 (3)°, and A/C 25.51 (9)°. These values show that the terminal planes are twisted in opposite sense with respect to the central bridging fragment. This situation is relatively rare, the majority of chalcones found in the CDB shows the same sense of rotation with respect to the central bridge.The bond lengths within the conjugated linear fragment suggest the large degree of localization: C—C bond length of 1.480 (4) Å, C=C of 1.329 (4)Å and C=O 1.232 (3) Å. The bond angles within the phenyl ring are influenced by both Cl and C=C– substituents, and these influences are almost additive, as suggested e.g., by Domenicano (1988). The distribution is almost symmetrical with respect to the C15···C18 line, and the values are close to those calculated by summing the effects of both substituents.In the crystal structure there is one relatively short C—H···O potential hydrogen bond, C17—H17···O12(x,1 + y,z), that link molecules into infinite chains along y direction, and few weak C—H···O and C—H···π contacts, which can stabilize the packing otherwise determined by the van der Waals interactions and close packing requirements (Fig. 2).supporting informationsup-2Acta Cryst. (2009). E65, o3255–o3256    S2. Experimental To a mixture of 1-acetonaphthone (1.7 g, 0.01 mol) and p-chlorobenzaldehyde (1.4 g, 0.01 mol) in 30 ml e thanol, 10 ml of 10% sodium hydroxide solution was added and stirred at 5–10 oC for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from DMF by slow evaporation method and yield of the compound was 82%. (m.p. 360–362 K). Analytical data: Found (Calculated): C %: 76.89 (77.95); H %: 4.23 (4.48).S3. Refinement Hydrogen atoms were located geometrically and refined as a riding model; their Uiso values were set at 1.2 times Ueq of their carrier carbon atom.Figure 1Anisotropic ellipsoid representation of the compound I together with atom labelling scheme. The ellipsoids are drawn at 50% probability level, hydrogen atoms are depicted as spheres with arbitrary radii. supporting informationsup-3Acta Cryst. (2009). E65, o3255–o3256    Figure 2The crystal packing of I as seen along z direction; weak C—H···O bonds are shown as dashed lines. Figure 3The formation of the title compound. (E)-3-(4-Chlorophenyl)-1-(1-naphthyl)prop-2-en-1-one Crystal data C19H13ClOMr = 292.74Monoclinic, PcHall symbol: P -2yca = 12.0392 (14) Åb = 8.0544 (5) Åc = 7.8472 (6) Åβ = 98.091 (10)°V = 753.36 (11) Å3Z = 2F(000) = 304Dx = 1.291 Mg m−3Mo Kα radiation, λ = 0.71073 ÅCell parameters from 1288 reflectionsθ = 2.5–26.6°µ = 0.25 mm−1T = 295 KBlock, colourless0.30 × 0.20 × 0.15 mmsupporting informationsup-4Acta Cryst. (2009). E65, o3255–o3256    Data collection Oxford Diffraction Xcalibur (Sapphire2, large Be window) diffractometerRadiation source: Enhance (Mo) X-ray SourceGraphite monochromatorDetector resolution: 8.1929 pixels mm-1ω scanAbsorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)Tmin = 0.667, Tmax = 1.0002481 measured reflections1866 independent reflections1440 reflections with I > 2σ(I)Rint = 0.014θmax = 26.6°, θmin = 2.5°h = −14→11k = −9→4l = −9→6Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.035wR(F2) = 0.083S = 0.961866 reflections190 parameters2 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) + (0.050P)2] where P = (Fo2 + 2Fc2)/3(Δ/σ)max = 0.001Δρmax = 0.12 e Å−3Δρmin = −0.13 e Å−3Absolute structure: Flack (1983), 423 Friedel pairsAbsolute structure parameter: 0.08 (7)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) x y z Uiso*/UeqC1 0.0117 (2) 0.4299 (3) 0.5052 (3) 0.0451 (6)C2 −0.0556 (2) 0.5690 (3) 0.4967 (3) 0.0543 (7)H2 −0.0256 0.6681 0.5435 0.065*C3 −0.1681 (2) 0.5651 (4) 0.4195 (4) 0.0618 (7)H3 −0.2119 0.6605 0.4154 0.074*C4 −0.2124 (2) 0.4207 (4) 0.3508 (4) 0.0617 (7)H4 −0.2879 0.4175 0.3048 0.074*C5 −0.1473 (2) 0.2754 (3) 0.3471 (3) 0.0521 (6)C6 −0.1908 (2) 0.1292 (4) 0.2642 (4) 0.0657 (7)H6 −0.2661 0.1256 0.2173 0.079*C7 −0.1260 (3) −0.0057 (4) 0.2513 (4) 0.0753 (9)H7 −0.1567 −0.1010 0.1967 0.090*C8 −0.0125 (3) −0.0015 (4) 0.3204 (4) 0.0697 (8)H8 0.0325 −0.0934 0.3084 0.084*supporting informationsup-5Acta Cryst. (2009). E65, o3255–o3256    C9 0.0335 (2) 0.1362 (3) 0.4058 (4) 0.0563 (7)H9 0.1088 0.1355 0.4528 0.068*C10 −0.0321 (2) 0.2793 (3) 0.4233 (3) 0.0469 (6)C11 0.1246 (2) 0.4368 (3) 0.6114 (3) 0.0526 (6)O12 0.16532 (16) 0.3125 (2) 0.6876 (3) 0.0740 (6)C13 0.1853 (2) 0.5973 (3) 0.6331 (3) 0.0562 (7)H13 0.1563 0.6890 0.5698 0.067*C14 0.2804 (2) 0.6132 (3) 0.7411 (4) 0.0581 (7)H14 0.3076 0.5175 0.7989 0.070*C15 0.3469 (2) 0.7639 (4) 0.7790 (4) 0.0543 (7)C16 0.3072 (2) 0.9202 (3) 0.7270 (4) 0.0637 (8)H16 0.2357 0.9297 0.6651 0.076*C17 0.3705 (2) 1.0620 (4) 0.7642 (4) 0.0682 (9)H17 0.3421 1.1656 0.7282 0.082*C18 0.4770 (2) 1.0472 (4) 0.8560 (4) 0.0674 (9)C19 0.5195 (2) 0.8945 (4) 0.9109 (4) 0.0711 (8)H19 0.5912 0.8856 0.9723 0.085*C20 0.4540 (2) 0.7544 (4) 0.8731 (4) 0.0674 (8)H20 0.4821 0.6514 0.9115 0.081*Cl21 0.55687 (8) 1.22525 (11) 0.90310 (13) 0.1042 (4)Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23C1 0.0455 (14) 0.0522 (15) 0.0381 (14) 0.0023 (11) 0.0074 (11) 0.0011 (12)C2 0.0602 (17) 0.0538 (15) 0.0500 (16) 0.0043 (12) 0.0113 (13) −0.0061 (13)C3 0.0541 (17) 0.0693 (18) 0.0619 (18) 0.0165 (13) 0.0081 (14) −0.0018 (16)C4 0.0477 (15) 0.085 (2) 0.0521 (16) 0.0047 (14) 0.0058 (12) 0.0001 (16)C5 0.0527 (15) 0.0656 (17) 0.0384 (15) −0.0037 (13) 0.0074 (12) 0.0013 (14)C6 0.0662 (18) 0.077 (2) 0.0528 (17) −0.0111 (17) 0.0052 (14) −0.0025 (17)C7 0.102 (3) 0.066 (2) 0.057 (2) −0.0178 (18) 0.0114 (18) −0.0110 (16)C8 0.104 (3) 0.0555 (17) 0.0522 (17) 0.0068 (16) 0.0217 (17) −0.0032 (15)C9 0.0653 (18) 0.0581 (15) 0.0469 (16) 0.0059 (13) 0.0126 (13) 0.0024 (14)C10 0.0550 (16) 0.0516 (14) 0.0364 (14) 0.0008 (12) 0.0144 (12) 0.0049 (12)C11 0.0533 (16) 0.0559 (16) 0.0491 (16) 0.0055 (12) 0.0090 (12) 0.0026 (13)O12 0.0674 (13) 0.0677 (12) 0.0812 (15) 0.0034 (10) −0.0100 (11) 0.0117 (12)C13 0.0557 (17) 0.0613 (16) 0.0510 (16) 0.0029 (12) 0.0059 (14) 0.0043 (13)C14 0.0491 (15) 0.0708 (17) 0.0544 (17) 0.0051 (13) 0.0071 (13) 0.0069 (15)C15 0.0413 (15) 0.073 (2) 0.0478 (16) −0.0009 (13) 0.0049 (12) 0.0011 (13)C16 0.0448 (16) 0.079 (2) 0.065 (2) −0.0034 (14) −0.0015 (13) 0.0077 (16)C17 0.0483 (17) 0.077 (2) 0.078 (2) −0.0085 (13) 0.0042 (15) 0.0113 (16)C18 0.0488 (18) 0.089 (2) 0.065 (2) −0.0120 (15) 0.0101 (15) −0.0020 (17)C19 0.0420 (16) 0.096 (2) 0.073 (2) 0.0000 (15) −0.0023 (14) −0.0061 (19)C20 0.0532 (17) 0.080 (2) 0.066 (2) 0.0088 (14) −0.0019 (14) 0.0034 (16)Cl21 0.0772 (5) 0.1122 (7) 0.1174 (8) −0.0353 (5) −0.0068 (5) −0.0004 (6)supporting informationsup-6Acta Cryst. (2009). E65, o3255–o3256    Geometric parameters (Å, º) C1—C2 1.379 (3) C9—H9 0.9300C1—C10 1.438 (3) C11—O12 1.232 (3)C1—C11 1.491 (3) C11—C13 1.483 (4)C2—C3 1.404 (4) C13—C14 1.331 (3)C2—H2 0.9300 C13—H13 0.9300C3—C4 1.359 (4) C14—C15 1.462 (4)C3—H3 0.9300 C14—H14 0.9300C4—C5 1.410 (4) C15—C16 1.387 (4)C4—H4 0.9300 C15—C20 1.395 (4)C5—C6 1.410 (4) C16—C17 1.382 (4)C5—C10 1.431 (3) C16—H16 0.9300C6—C7 1.350 (4) C17—C18 1.385 (4)C6—H6 0.9300 C17—H17 0.9300C7—C8 1.398 (4) C18—C19 1.378 (4)C7—H7 0.9300 C18—Cl21 1.737 (3)C8—C9 1.371 (4) C19—C20 1.385 (4)C8—H8 0.9300 C19—H19 0.9300C9—C10 1.415 (3) C20—H20 0.9300C2—C1—C10 119.2 (2) C5—C10—C1 118.6 (2)C2—C1—C11 118.7 (2) O12—C11—C13 119.8 (3)C10—C1—C11 122.0 (2) O12—C11—C1 120.6 (2)C1—C2—C3 121.9 (3) C13—C11—C1 119.5 (2)C1—C2—H2 119.1 C14—C13—C11 121.5 (3)C3—C2—H2 119.1 C14—C13—H13 119.2C4—C3—C2 119.4 (3) C11—C13—H13 119.2C4—C3—H3 120.3 C13—C14—C15 127.3 (3)C2—C3—H3 120.3 C13—C14—H14 116.3C3—C4—C5 122.0 (2) C15—C14—H14 116.3C3—C4—H4 119.0 C16—C15—C20 117.4 (3)C5—C4—H4 119.0 C16—C15—C14 122.5 (2)C4—C5—C6 122.1 (2) C20—C15—C14 120.1 (3)C4—C5—C10 118.8 (2) C17—C16—C15 122.1 (3)C6—C5—C10 119.1 (2) C17—C16—H16 119.0C7—C6—C5 121.7 (3) C15—C16—H16 119.0C7—C6—H6 119.1 C16—C17—C18 118.8 (3)C5—C6—H6 119.1 C16—C17—H17 120.6C6—C7—C8 119.7 (3) C18—C17—H17 120.6C6—C7—H7 120.1 C19—C18—C17 121.0 (3)C8—C7—H7 120.1 C19—C18—Cl21 120.0 (2)C9—C8—C7 121.0 (3) C17—C18—Cl21 118.9 (3)C9—C8—H8 119.5 C18—C19—C20 119.0 (3)C7—C8—H8 119.5 C18—C19—H19 120.5C8—C9—C10 120.9 (3) C20—C19—H19 120.5C8—C9—H9 119.5 C19—C20—C15 121.6 (3)C10—C9—H9 119.5 C19—C20—H20 119.2supporting informationsup-7Acta Cryst. (2009). E65, o3255–o3256    C9—C10—C5 117.6 (2) C15—C20—H20 119.2C9—C10—C1 123.7 (2)C10—C1—C2—C3 4.0 (4) C11—C1—C10—C5 170.1 (2)C11—C1—C2—C3 −171.1 (2) C2—C1—C11—O12 146.6 (3)C1—C2—C3—C4 −0.1 (4) C10—C1—C11—O12 −28.3 (4)C2—C3—C4—C5 −3.1 (4) C2—C1—C11—C13 −29.9 (3)C3—C4—C5—C6 −175.0 (3) C10—C1—C11—C13 155.1 (2)C3—C4—C5—C10 2.1 (4) O12—C11—C13—C14 −3.9 (4)C4—C5—C6—C7 175.5 (3) C1—C11—C13—C14 172.7 (2)C10—C5—C6—C7 −1.6 (4) C11—C13—C14—C15 −178.0 (3)C5—C6—C7—C8 −0.4 (4) C13—C14—C15—C16 11.7 (4)C6—C7—C8—C9 1.9 (4) C13—C14—C15—C20 −169.2 (3)C7—C8—C9—C10 −1.3 (4) C20—C15—C16—C17 0.6 (4)C8—C9—C10—C5 −0.7 (3) C14—C15—C16—C17 179.7 (3)C8—C9—C10—C1 −177.5 (2) C15—C16—C17—C18 0.2 (4)C4—C5—C10—C9 −175.1 (2) C16—C17—C18—C19 −0.4 (4)C6—C5—C10—C9 2.1 (3) C16—C17—C18—Cl21 −180.0 (2)C4—C5—C10—C1 1.9 (3) C17—C18—C19—C20 −0.1 (4)C6—C5—C10—C1 179.1 (2) Cl21—C18—C19—C20 179.4 (2)C2—C1—C10—C9 171.9 (2) C18—C19—C20—C15 0.9 (4)C11—C1—C10—C9 −13.2 (4) C16—C15—C20—C19 −1.2 (4)C2—C1—C10—C5 −4.8 (3) C14—C15—C20—C19 179.7 (3)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AC17—H17···O12i 0.93 2.42 3.180 (4) 139C3—H3···Cl21ii 0.93 2.92 3.703 (3) 143C8—H8···O12iii 0.93 2.64 3.546 (4) 163Symmetry codes: (i) x, y+1, z; (ii) x−1, −y+2, z−1/2; (iii) x, −y, z−1/2.

(E)-3-(4-Chloro­phen­yl)-1-(1-naphth­yl)prop-2-en-1-one

In the title compound, C(19)H(13)ClO, the benzene ring and the naphthalene system, are twisted by 12.3 (3) and 36.1 (2)degrees, respectively, and in opposite directions with respect to the central propenone bridge. The bond-angle pattern within the benzene ring is influence by both substituents; these influences are almost additive. In the crystal, the molecules are linked by C-H center dot center dot center dot O and C-H center dot center dot center dot Cl interactions

(E)-3-(4-Chlorophenyl)-1-(1-naphthyl)prop-2-en-1-one

In the title compound, C19H13ClO, the benzene ring and the naphthalene system, are twisted by 12.3&amp;#8197;(3) and 36.1&amp;#8197;(2)&amp;#176;, respectively, and in opposite directions with respect to the central propenone bridge. The bond-angle pattern within the benzene ring is influence by both substituents; these influences are almost additive. In the crystal, the molecules are linked by C&amp;#8212;H...O and C&amp;#8212;H...Cl interactions

Maciej Kubicki

H. S. Yathirajan

B. Narayana

S. Samshuddin

Grzegorz Dutkiewicz

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Acta Crystallographica Section E Structure Reports Online

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                    E

Acta Cryst.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) x y z Uiso*/Ueqsupplementary materials sup-4

Growth, 295, 54–59. organic compounds Acta Cryst.

In Stereochemical Applications of gas-phase electron diffraction, edited by I.

organic compounds o3256 Dutkiewicz et al. C19H13ClO Acta Cryst.

Stereochemical Workstation Operation Manual. Siemens Analytical X-ray Instruments Inc.,

The formation of the title compound. (E)-3-(4-Chlorophenyl)-1-(1-naphthyl)prop-2-en-1-one Crystal data

http://eprints.uni-mysore.ac.in/9955/1/%28E%29-3-%284-Chloro%C2%ADphen%C2%ADyl%29-1.pdf

(E)-3-(4-Chlorophenyl)-1-(1-naphthyl)prop-2-en-1-one

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(E)-3-(4-Chloro­phen­yl)-1-(1-naphth­yl)prop-2-en-1-one

Abstract

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Full text

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

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

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(E)-3-(4-Chlorophenyl)-1-(1-naphthyl)prop-2-en-1-one