Abd alla

Awadallah

B. Kalluraya

Bausch

D. Revannasiddaiah

Khalil

M. K. Usha

Macrae

N. K. Lokanath

P. C. Shyma

S. Madan Kumar

Sheldrick

Spek

Acta Crystallographica Section E

English

In the title compound, C18H14N2O, the dihedral angle between the methylphenyl ring and the phthalazone ring system (r.m.s. deviation = 0.034 Å) is 53.93 (9)°. In the crystal, molecules are connected by C—H...O hydrogen bonds, forming chains along [101]. The chains are linked by π–π interactions [centroid–centroid distance 3.6990 (12) Å], forming layers parallel to (10-1).</jats:p

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4-(4-Methylphenyl)-2-(prop-2-yn-1-yl)-phthalazin-1(2H)-oneM. K. Usha,a S. Madan Kumar,a P. C. Shyma,bB. Kalluraya,b N. K. Lokanatha and D. Revannasiddaiaha*aDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore570 006, India, and bDepartment of Studies in Chemistry, Mangalore University,Mangalagangotri, Mangalore 574 199, IndiaCorrespondence e-mail: dr@physics.uni-mysore.ac.inReceived 26 December 2013; accepted 30 December 2013Key indicators: single-crystal X-ray study; T = 296 K; mean (C–C) = 0.002 A˚;R factor = 0.044; wR factor = 0.132; data-to-parameter ratio = 12.2.In the title compound, C18H14N2O, the dihedral angle betweenthe methylphenyl ring and the phthalazone ring system (r.m.s.deviation = 0.034 A˚) is 53.93 (9). In the crystal, molecules areconnected by C—H  O hydrogen bonds, forming chainsalong [101]. The chains are linked by – interactions[centroid–centroid distance 3.6990 (12) A˚], forming layersparallel to (101).Related literatureFor general background and the biological and pharmacolo-gical properties of phthalazine derivatives, see: Abd alla et al.(2010); Awadallah et al. (2012); Khalil et al. (2009); Kim et al.(2008); Ryu et al. (2007). For a related structure, see: Bausch etal. (1997).ExperimentalCrystal dataC18H14N2OMr = 274.31Monoclinic, P21=na = 11.9917 (19) A˚b = 9.7116 (16) A˚c = 12.602 (2) A˚ = 101.285 (7)V = 1439.2 (4) A˚3Z = 4Cu K radiation = 0.63 mm1T = 296 K0.23  0.20  0.19 mmData collectionBruker X8 Proteum diffractometerAbsorption correction: multi-scan(SADABS; Bruker, 2013)Tmin = 0.864, Tmax = 0.8868733 measured reflections2337 independent reflections2093 reflections with I > 2(I)Rint = 0.036RefinementR[F 2 > 2(F 2)] = 0.044wR(F 2) = 0.132S = 1.102337 reflections192 parametersH-atom parameters constrainedmax = 0.15 e A˚3min = 0.15 e A˚3Table 1Hydrogen-bond geometry (A˚, ).D—H  A D—H H  A D  A D—H  AC6—H6  O1i 0.93 2.45 3.322 (2) 157Symmetry code: (i) x 12;y 12; z 12.Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT(Bruker, 2013); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:Mercury (Macrae et al., 2008); software used to prepare material forpublication: PLATON (Spek, 2009).The authors are grateful to the IOE, University of Mysore,for providing the single-crystal X-ray diffraction facility. MKUis grateful to the DST, New Delhi, for the award of anINSPIRE Fellowship. DR acknowledges the UGC, NewDelhi, for financial support under the Major Research ProjectScheme [No. F.41–882/2012 (SR)].Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: IS5329).ReferencesAbd alla, M. S. M., Hegab, M. I., Taleb, N. A. A., Hasabelnaby, S. M. &Goudah, A. (2010). Eur. J. Med. Chem. 45, 1267–1277.Awadallah, F. M., El-Eraky, W. I. & Saleh, D. O. (2012). Eur. J. Med. Chem. 52,14–21.Bausch, M. J., Robinson, P. D. & Gong, Y. (1997). Acta Cryst. C53, 517–519.Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison,-Wisconsin, USA.Khalil, A. M., Berghot, M. A. & Gouda, M. A. (2009). Eur. J. Med. Chem. 44,4448–4454.Kim, J. S., Rhee, H.-K., Park, H. J., Lee, S. K., Lee, C.-O. & Choo, H.-Y. P.(2008). Bioorg. Med. Chem. 16, 4545–4550.Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P.,Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood,P. A. (2008). J. Appl. Cryst. 41, 466–470.Ryu, C.-K., Park, R.-E., Ma, M.-Y. & Nho, J.-H. (2007). Bioorg. Med. Chem.Lett. 17, 2477–2580.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.organic compoundso138 Usha et al. doi:10.1107/S1600536813034880 Acta Cryst. (2014). E70, o138Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supporting informationsup-1Acta Cryst. (2014). E70, o138    supporting informationActa Cryst. (2014). E70, o138    [doi:10.1107/S1600536813034880]4-(4-Methylphenyl)-2-(prop-2-yn-1-yl)phthalazin-1(2H)-oneM. K. Usha, S. Madan Kumar, P. C. Shyma, B. Kalluraya, N. K. Lokanath and D. RevannasiddaiahS1. Comment Nitrogen heterocyclic compounds have received a great attention because of their wide applicability in different areas, especially drugs (Kim et al., 2008). Phthalazines are an important class of nitrogen heterocyclic compounds that possess exciting pharmacological and biological properties (Khalil et al., 2009). Phthalazines have been reported to possess antifungal (Ryu et al., 2007), antibacterial (Khalil et al., 2009), cytotoxic (Kim et al., 2008), anti-inflammatory (Abd alla et al., 2010), antihypertensive and vasorelaxant (Awadallah et al., 2012) properties. As part of our studies in this area, herewith we report the structure of the title compound.The ORTEP of the title compound is shown (Fig. 1). The phthalazine ring is nearly planar. The dihedral angle between the methylphenyl ring and the phenyl ring of the phthalazinone moiety is 53.93 (9)°. The bond lengths and bond angles of the title compound are comparable to related structure, 4-(9-fluorenoxy)-2-phenylphthalazin-1(2H)-one (Bausch et al., 1997). In the crystal structure, molecules are connected by intermolecular C—H···O hydrogen bonds (Fig. 2). Also, short contacts of the type π–π are observed [minimum centroid-centroid distance 3.6990 (12) Å].S2. Experimental 2-(4-Methylbenzoyl)benzoic acid (0.1 mol) is esterified in ethanol (25 ml) in presence of few drops of sulfuric acid. The ethyl 2-(4-methylbenzoyl)benzoate obtained is further refluxed with hydrazine hydrate (5 ml, 98%) in absolute ethanol (50 ml)for 2 hrs. Solid obtained on cooling was filtered off and dried to give 4-(4-methylphenyl)phthalazin-1-ol. A mixture of 4-(4-methylphenyl)phthalazin-1-ol (0.015 mol), anhydrous potassium carbonate (3.04 g, 0.022 mol) and propargylbromide (1.78 g, 0.015 mol) in DMF (25 ml) was stirred at 65 °C for 2 h. After completion of reaction, reaction mixture was poured into ice-cold water. The solid product obtained was purified by column chromatography using n-hexane and ethyl acetate as eluent to get pure compound. Further the compound was recrystallized from ethyl acetate to get the yellow crystals (m.p. 168–170 °C).S3. Refinement The H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and refined as riding with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(Cmethyl).supporting informationsup-2Acta Cryst. (2014). E70, o138    Figure 1ORTEP diagram of the title compound with 50% probability ellipsoids. supporting informationsup-3Acta Cryst. (2014). E70, o138    Figure 2Packing diagram of the title compound, viewed along the c axis. 4-(4-Methylphenyl)-2-(prop-2-yn-1-yl)phthalazin-1(2H)-one Crystal data C18H14N2OMr = 274.31Monoclinic, P21/nHall symbol: -P 2yna = 11.9917 (19) Åb = 9.7116 (16) Åc = 12.602 (2) Åβ = 101.285 (7)°V = 1439.2 (4) Å3Z = 4F(000) = 576Dx = 1.266 Mg m−3Cu Kα radiation, λ = 1.54178 ÅCell parameters from 2337 reflectionsθ = 4.7–64.6°µ = 0.63 mm−1T = 296 KBlock, yellow0.23 × 0.20 × 0.19 mmData collection Bruker X8 Proteum diffractometerRadiation source: Bruker MicroStar microfocus rotating anodeHelios multilayer optics monochromatorDetector resolution: 10.7 pixels mm-1φ and ω scansAbsorption correction: multi-scan (SADABS; Bruker, 2013)Tmin = 0.864, Tmax = 0.8868733 measured reflections2337 independent reflections2093 reflections with I > 2σ(I)Rint = 0.036θmax = 64.6°, θmin = 4.7°h = −13→12k = −10→11l = −8→14Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.044wR(F2) = 0.132S = 1.102337 reflections192 parameters0 restraintsPrimary atom site location: structure-invariant direct methodsSecondary atom site location: difference Fourier mapsupporting informationsup-4Acta Cryst. (2014). E70, o138    Hydrogen site location: inferred from neighbouring sitesH-atom parameters constrainedw = 1/[σ2(Fo2) + (0.0698P)2 + 0.2752P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max = 0.003Δρmax = 0.15 e Å−3Δρmin = −0.15 e Å−3Extinction correction: SHELXL, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4Extinction coefficient: 0.0090 (9)Special details Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion anglesRefinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs 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*/UeqO1 0.19809 (12) −0.11059 (16) 1.21105 (8) 0.0755 (5)N1 0.22126 (12) 0.03101 (14) 0.95663 (10) 0.0524 (4)N2 0.23069 (12) 0.00807 (15) 1.06549 (10) 0.0548 (5)C1 0.07580 (12) −0.14488 (16) 0.92636 (11) 0.0464 (5)C2 0.09215 (13) −0.17108 (17) 1.03779 (11) 0.0486 (5)C3 0.17640 (14) −0.09248 (18) 1.11276 (12) 0.0536 (5)C4 0.14781 (13) −0.04216 (16) 0.88990 (11) 0.0468 (5)C5 −0.01049 (14) −0.21765 (18) 0.85760 (13) 0.0562 (5)C6 −0.07462 (15) −0.3140 (2) 0.89874 (15) 0.0645 (6)C7 −0.05524 (16) −0.3416 (2) 1.00855 (15) 0.0647 (6)C8 0.02715 (15) −0.27061 (19) 1.07770 (14) 0.0588 (6)C9 0.31525 (16) 0.0952 (2) 1.13355 (14) 0.0646 (6)C10 0.43037 (18) 0.0402 (2) 1.14605 (14) 0.0653 (7)C11 0.5226 (2) −0.0013 (3) 1.1548 (2) 0.0997 (10)C12 0.14520 (13) −0.01379 (17) 0.77355 (12) 0.0473 (5)C13 0.13700 (15) 0.11933 (18) 0.73343 (13) 0.0554 (6)C14 0.13974 (16) 0.1456 (2) 0.62603 (13) 0.0604 (6)C15 0.15141 (14) 0.0409 (2) 0.55518 (12) 0.0567 (6)C16 0.15944 (16) −0.0918 (2) 0.59542 (13) 0.0638 (6)C17 0.15584 (16) −0.11952 (19) 0.70219 (13) 0.0583 (6)C18 0.15649 (17) 0.0690 (2) 0.43701 (13) 0.0708 (7)H5 −0.02440 −0.20060 0.78360 0.0670*H6 −0.13170 −0.36110 0.85220 0.0770*H7 −0.09810 −0.40830 1.03530 0.0780*H8 0.03990 −0.28870 1.15150 0.0710*H9A 0.31310 0.18630 1.10180 0.0770*H9B 0.29570 0.10410 1.20440 0.0770*H11 0.59650 −0.03440 1.16180 0.1200*H13 0.12950 0.19220 0.77940 0.0660*supporting informationsup-5Acta Cryst. (2014). E70, o138    H14 0.13360 0.23590 0.60110 0.0720*H16 0.16750 −0.16440 0.54940 0.0760*H17 0.16060 −0.21010 0.72650 0.0700*H18A 0.12210 0.15650 0.41580 0.1060*H18B 0.11620 −0.00210 0.39220 0.1060*H18C 0.23440 0.07020 0.42870 0.1060*Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23O1 0.0829 (9) 0.1064 (11) 0.0305 (6) −0.0022 (8) −0.0054 (6) 0.0047 (6)N1 0.0592 (8) 0.0597 (8) 0.0341 (7) 0.0033 (6) −0.0011 (6) −0.0022 (6)N2 0.0602 (8) 0.0656 (9) 0.0324 (7) 0.0008 (7) −0.0062 (6) −0.0062 (6)C1 0.0452 (8) 0.0546 (9) 0.0356 (8) 0.0106 (7) −0.0011 (6) −0.0001 (6)C2 0.0463 (8) 0.0616 (10) 0.0347 (8) 0.0120 (7) 0.0004 (6) 0.0012 (7)C3 0.0546 (9) 0.0684 (11) 0.0338 (8) 0.0099 (8) −0.0010 (7) −0.0002 (7)C4 0.0485 (8) 0.0534 (9) 0.0340 (8) 0.0077 (7) −0.0029 (6) −0.0022 (6)C5 0.0558 (9) 0.0676 (11) 0.0398 (8) 0.0020 (8) −0.0041 (7) −0.0023 (7)C6 0.0544 (10) 0.0732 (12) 0.0611 (11) −0.0037 (9) −0.0001 (8) −0.0053 (9)C7 0.0560 (10) 0.0724 (12) 0.0646 (11) −0.0008 (9) 0.0089 (8) 0.0059 (9)C8 0.0555 (9) 0.0757 (12) 0.0446 (9) 0.0087 (8) 0.0084 (7) 0.0102 (8)C9 0.0735 (12) 0.0688 (12) 0.0429 (9) −0.0040 (9) −0.0094 (8) −0.0117 (8)C10 0.0669 (12) 0.0716 (12) 0.0519 (10) −0.0129 (9) −0.0015 (8) −0.0003 (8)C11 0.0672 (15) 0.0930 (17) 0.135 (2) −0.0067 (13) 0.0102 (14) 0.0109 (15)C12 0.0463 (8) 0.0578 (9) 0.0338 (8) 0.0043 (7) −0.0016 (6) −0.0019 (6)C13 0.0683 (10) 0.0552 (10) 0.0416 (9) −0.0007 (8) 0.0081 (7) −0.0051 (7)C14 0.0725 (11) 0.0613 (10) 0.0462 (9) −0.0006 (8) 0.0089 (8) 0.0060 (8)C15 0.0498 (9) 0.0820 (12) 0.0360 (8) −0.0015 (8) 0.0027 (7) −0.0015 (8)C16 0.0757 (12) 0.0726 (12) 0.0424 (9) 0.0067 (9) 0.0102 (8) −0.0125 (8)C17 0.0726 (11) 0.0572 (10) 0.0434 (9) 0.0116 (8) 0.0075 (8) −0.0021 (7)C18 0.0664 (11) 0.1084 (16) 0.0362 (9) −0.0050 (11) 0.0064 (8) 0.0095 (9)Geometric parameters (Å, º) O1—C3 1.2275 (18) C14—C15 1.378 (3)N1—N2 1.3725 (18) C15—C16 1.381 (3)N1—C4 1.303 (2) C15—C18 1.527 (2)N2—C3 1.373 (2) C16—C17 1.381 (2)N2—C9 1.463 (2) C5—H5 0.9300C1—C2 1.4026 (19) C6—H6 0.9300C1—C4 1.452 (2) C7—H7 0.9300C1—C5 1.404 (2) C8—H8 0.9300C2—C3 1.457 (2) C9—H9A 0.9700C2—C8 1.396 (2) C9—H9B 0.9700C4—C12 1.486 (2) C11—H11 0.9300C5—C6 1.375 (3) C13—H13 0.9300C6—C7 1.384 (3) C14—H14 0.9300C7—C8 1.369 (3) C16—H16 0.9300supporting informationsup-6Acta Cryst. (2014). E70, o138    C9—C10 1.460 (3) C17—H17 0.9300C10—C11 1.162 (3) C18—H18A 0.9600C12—C13 1.385 (2) C18—H18B 0.9600C12—C17 1.387 (2) C18—H18C 0.9600C13—C14 1.384 (2)N2—N1—C4 118.01 (13) C15—C16—C17 121.75 (17)N1—N2—C3 126.58 (13) C12—C17—C16 120.78 (17)N1—N2—C9 113.85 (13) C1—C5—H5 120.00C3—N2—C9 119.36 (13) C6—C5—H5 120.00C2—C1—C4 117.79 (13) C5—C6—H6 120.00C2—C1—C5 117.93 (14) C7—C6—H6 120.00C4—C1—C5 124.26 (13) C6—C7—H7 120.00C1—C2—C3 119.84 (14) C8—C7—H7 120.00C1—C2—C8 120.52 (14) C2—C8—H8 120.00C3—C2—C8 119.64 (13) C7—C8—H8 120.00O1—C3—N2 121.00 (16) N2—C9—H9A 109.00O1—C3—C2 124.23 (16) N2—C9—H9B 109.00N2—C3—C2 114.77 (13) C10—C9—H9A 109.00N1—C4—C1 122.64 (13) C10—C9—H9B 109.00N1—C4—C12 114.62 (14) H9A—C9—H9B 108.00C1—C4—C12 122.73 (13) C10—C11—H11 180.00C1—C5—C6 120.59 (15) C12—C13—H13 119.00C5—C6—C7 120.79 (17) C14—C13—H13 120.00C6—C7—C8 119.87 (18) C13—C14—H14 119.00C2—C8—C7 120.25 (16) C15—C14—H14 119.00N2—C9—C10 112.59 (16) C15—C16—H16 119.00C9—C10—C11 178.6 (2) C17—C16—H16 119.00C4—C12—C13 121.31 (14) C12—C17—H17 120.00C4—C12—C17 121.03 (15) C16—C17—H17 120.00C13—C12—C17 117.61 (14) C15—C18—H18A 109.00C12—C13—C14 121.04 (16) C15—C18—H18B 109.00C13—C14—C15 121.49 (17) C15—C18—H18C 110.00C14—C15—C16 117.33 (15) H18A—C18—H18B 109.00C14—C15—C18 121.90 (17) H18A—C18—H18C 109.00C16—C15—C18 120.77 (16) H18B—C18—H18C 109.00C4—N1—N2—C3 5.4 (2) C8—C2—C3—O1 2.6 (3)C4—N1—N2—C9 −179.97 (16) C8—C2—C3—N2 −176.34 (16)N2—N1—C4—C1 0.6 (2) C1—C2—C8—C7 −1.5 (3)N2—N1—C4—C12 −178.36 (14) C3—C2—C8—C7 177.55 (17)N1—N2—C3—O1 174.12 (16) N1—C4—C12—C13 −50.0 (2)N1—N2—C3—C2 −6.9 (2) N1—C4—C12—C17 127.20 (17)C9—N2—C3—O1 −0.3 (3) C1—C4—C12—C13 131.06 (17)C9—N2—C3—C2 178.71 (15) C1—C4—C12—C17 −51.7 (2)N1—N2—C9—C10 −83.42 (18) C1—C5—C6—C7 −0.2 (3)C3—N2—C9—C10 91.67 (19) C5—C6—C7—C8 1.3 (3)C4—C1—C2—C3 2.2 (2) C6—C7—C8—C2 −0.4 (3)supporting informationsup-7Acta Cryst. (2014). E70, o138    C4—C1—C2—C8 −178.72 (15) C4—C12—C13—C14 177.07 (16)C5—C1—C2—C3 −176.58 (15) C17—C12—C13—C14 −0.2 (3)C5—C1—C2—C8 2.5 (2) C4—C12—C17—C16 −176.53 (17)C2—C1—C4—N1 −4.1 (2) C13—C12—C17—C16 0.8 (3)C2—C1—C4—C12 174.76 (15) C12—C13—C14—C15 −0.4 (3)C5—C1—C4—N1 174.61 (16) C13—C14—C15—C16 0.5 (3)C5—C1—C4—C12 −6.5 (2) C13—C14—C15—C18 −178.98 (17)C2—C1—C5—C6 −1.6 (2) C14—C15—C16—C17 0.1 (3)C4—C1—C5—C6 179.67 (16) C18—C15—C16—C17 179.55 (18)C1—C2—C3—O1 −178.30 (17) C15—C16—C17—C12 −0.7 (3)C1—C2—C3—N2 2.7 (2)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AC6—H6···O1i 0.93 2.45 3.322 (2) 157Symmetry code: (i) x−1/2, −y−1/2, z−1/2.

Acta Crystallographica Section E Structure Reports Online

4-(4-Methylphenyl)-2-(prop-2-yn-1-yl)phthalazin-1(2<i>H</i>)-one

http://journals.iucr.org/e/issues/2014/02/00/is5329/is5329.pdf

4-(4-Methylphenyl)-2-(prop-2-yn-1-yl)phthalazin-1(2
                    H

4-(4-Methylphenyl)-2-(prop-2-yn-1-yl)phthalazin-1(2 H

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