Arfan

Bartroli

Chandra, 

G. M. Raghavendra

K. Mantelingu

Kung

M. Mahendra

Mannschreck

S. Jeyaseelan

Sheldrick

Spek

Acta Crystallographica Section E

English

null Chandra

Crossref

2-(1,3-Benzodioxol-5-yl)-3-phenyl-quinazolin-4(3H)-oneChandra,a G. M. Raghavendra,b S. Jeyaseelan,cK. Mantelingub and M. Mahendraa*aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore570 006, India, bDepartment of Studies in Chemistry, Manasagangotri, University ofMysore, Mysore 570 006, India, and cDepartment of Physics, St Philomena’sCollege, Mysore, IndiaCorrespondence e-mail: mahendra@physics.uni-mysore.ac.inReceived 7 June 2013; accepted 12 June 2013Key indicators: single-crystal X-ray study; T = 273 K; mean (C–C) = 0.003 Å;R factor = 0.040; wR factor = 0.101; data-to-parameter ratio = 16.0.In the molecule of the title compound, C21H14N2O3, thequinazoline ring system [maximum deviation = 0.076 (1) Å]makes dihedral angles of 40.57 (9) and 42.31 (11), respec-tively, with the phenyl and 1,3-benzodioxole rings. Thedihedral angle between the phenyl ring and the 1,3-benzodioxole ring is 4.34 (10). In the crystal, C—H  Ohydrogen bonds link the molecules into infinite zigzag chainsextending along [100].Related literatureFor the biological and pharmaceutical importance of quina-zolines, see: Arfan et al. (2008); Bartroli et al. (1998); Kung etal. (1999); Mannschreck et al. (1984).ExperimentalCrystal dataC21H14N2O3 Mr = 342.34Monoclinic, P21a = 8.984 (4) Åb = 6.056 (3) Åc = 15.248 (6) Å = 95.357 (6)V = 826.0 (6) Å3Z = 2Mo K radiation = 0.09 mm1T = 273 K0.30  0.25  0.20 mmData collectionBruker APEXII CCD area-detectordiffractometer9157 measured reflections3751 independent reflections3163 reflections with I > 2(I)Rint = 0.023RefinementR[F 2 > 2(F 2)] = 0.040wR(F 2) = 0.101S = 1.043751 reflections235 parameters1 restraintH-atom parameters constrainedmax = 0.16 e Å3min = 0.20 e Å3Table 1Hydrogen-bond geometry (Å, ).D—H  A D—H H  A D  A D—H  AC17—H17  O5i 0.93 2.37 3.185 (3) 146C25—H23A  O5ii 0.97 2.49 3.416 (3) 160Symmetry codes: (i) x; y þ 1; z; (ii) x 1; yþ 1; z.Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT(Bruker, 2009); data reduction: SAINT; program(s) used to solvestructure: SHELXS97 (Sheldrick, 2008); program(s) used to refinestructure: SHELXL97 (Sheldrick, 2008); molecular graphics:PLATON (Spek, 2009); software used to prepare material forpublication: SHELXL97.Chandra would like to thank the University of Mysore forthe award of an RFSMS fellowship under the head DV5/Physics/389/RFSMS/2009–2010/10.07.2012.Supplementary data and figures for this paper are available from theIUCr electronic archives (Reference: FK2072).ReferencesArfan, M., Khan, R., Imran, M., Khan, H. & Mehmood, J. (2008). J. Chem. Soc.Pak. 30, 299–305.Bartroli, J., Turmo, E., Alguero, M., Boncompte, E., Vericat, M. L., Conte, L.,Ramis, J., Merlos, M., Garcia-Rafanell, J. & Forn, J. (1998). J. Med. Chem.41, 1869–1882.Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin,USA.Kung, P. P., Casper, M. D., Cook, K. L., Wilson-Lingardo, L., Risen, L. M.,Vickers, T. A., Ranken, R., Blyn, L. B., Wyatt, J. R., Cook, P. & Decker, D. J.(1999). J. Med. Chem. 42, 4705–4713.Mannschreck, A., Koller, H., Stuhler, G., Davis, M. A. & Traber, J. (1984). Eur.J. Med. Chem. 19, 381–383.Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.Spek, A. L. (2009). Acta Cryst. D65, 148–155.organic compoundsActa Cryst. (2013). E69, o1113 doi:10.1107/S1600536813016346 Chandra et al. o1113Acta Crystallographica Section EStructure ReportsOnlineISSN 1600-5368supporting informationsup-1Acta Cryst. (2013). E69, o1113    supporting informationActa Cryst. (2013). E69, o1113    [https://doi.org/10.1107/S1600536813016346]2-(1,3-Benzodioxol-5-yl)-3-phenylquinazolin-4(3H)-oneChandra, G. M. Raghavendra, S. Jeyaseelan, K. Mantelingu and M. MahendraS1. Comment Quinazoline and their derivatives are an interesting class of heterocyclic compounds that have drawn much attention because of their biological and pharmaceutical activities; such as anti-bacterial (Kung et al., 1999), antimicrobial (Arfan et al., 2008) antifungal (Bartroli et al., 1998) and anticonvulsant activities (Mannschreck et al., 1984). In view of their importance, the crystal structure determination of the title compound was carried out and the results are presented herein.In the molecular structure of the title compound (Fig. 1), the dihedral angles between the quinazoline moiety (N3–C4/C6–C11/N1–C2) and the phenyl ring (C12/C13/C14/C15/C16/C17) as well as the 1,3-benzodioxole ring (C18–C19/C20–C24/C25–C26) are 40.57 (9)° and 42.31 (11)°, respectively. The dihedral angle between the phenyl ring (C12/C13/C14/C15/C16/C17) and 1,3-benzodioxole ring (C18–C19/C20–C24/C25–C26) is 4.34 (10)°. The crystal packing exhibits intermolecular C—H···O interactions (Fig. 2) that link molecules into endless zig-zag chains extended along [100].S2. Experimental To a solution of 2-amino-N-phenylbenzamide (1 mmol) and benzo[d][1,3]dioxole-5-carbaldehyde (1 mmol) in ethyl acetate (2 ml) was added propyl phosphonic anhydride (1 mmol) and the reaction mixture was stirred for about 2 hrs at room temperature, then 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) (1 mmol) was added and stirred for about 30 minutes. The reaction mixture was diluted with water and extracted to ethyl acetate and it was washed with 10% NaHCO3, water, brine solution and dried over anhydrous sodium sulfate and concentrated under reduced pressure to get a crude product which was recrystalized by slow evaporation in ethyl acetate at room temperature to get the title compound.S3. Refinement H atoms were placed at idealized positions and allowed to ride on their parent atoms with C–H distances in the range of 0.93 to 0.97 Å; Uiso(H) = 1.2Ueq(C).The title compound crystallizes in the non-centrosymmetric space group P 21; however, in the absence of significant anomalous scattering effects, the Flack parameter is essentially meaningless.supporting informationsup-2Acta Cryst. (2013). E69, o1113    Figure 1Molecular structure of the title compound with anisotropic displacement ellipsoids drawn at the 50% probability level. Figure 2Packing diagram of the molecule viewed along b-axis. Intermolecular hydrogen bonding drawn as dotted lines. supporting informationsup-3Acta Cryst. (2013). E69, o1113    2-(1,3-Benzodioxol-5-yl)-3-phenylquinazolin-4(3H)-one Crystal data C21H14N2O3Mr = 342.34Monoclinic, P21Hall symbol: P 2yba = 8.984 (4) Åb = 6.056 (3) Åc = 15.248 (6) Åβ = 95.357 (6)°V = 826.0 (6) Å3Z = 2F(000) = 356Dx = 1.377 Mg m−3Mo Kα radiation, λ = 0.71073 ÅCell parameters from 3751 reflectionsθ = 1.3–28.0°µ = 0.09 mm−1T = 273 KBlock, yellow0.30 × 0.25 × 0.20 mmData collection Bruker APEXII CCD area-detector diffractometerω and φ scans9157 measured reflections3751 independent reflections3163 reflections with I > 2σ(I)Rint = 0.023θmax = 28.0°, θmin = 1.3°h = −11→11k = −8→7l = −19→19Refinement Refinement on F2Least-squares matrix: fullR[F2 > 2σ(F2)] = 0.040wR(F2) = 0.101S = 1.043751 reflections235 parameters1 restraintPrimary 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) + (0.0558P)2 + 0.0215P] where P = (Fo2 + 2Fc2)/3(Δ/σ)max < 0.001Δρmax = 0.16 e Å−3Δρmin = −0.20 e Å−3Special 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*/UeqO5 1.05179 (14) 0.2056 (2) 0.70071 (8) 0.0591 (4)O24 0.44816 (14) 1.2103 (3) 0.88187 (8) 0.0637 (4)O26 0.47712 (16) 1.2832 (2) 0.73629 (9) 0.0690 (5)N1 0.69195 (15) 0.5808 (3) 0.61645 (9) 0.0552 (5)N3 0.88645 (14) 0.4809 (2) 0.72424 (8) 0.0416 (4)C2 0.76074 (16) 0.6048 (3) 0.69362 (10) 0.0435 (5)supporting informationsup-4Acta Cryst. (2013). E69, o1113    C4 0.93930 (17) 0.3085 (3) 0.67377 (10) 0.0443 (5)C6 0.85398 (17) 0.2701 (3) 0.58978 (11) 0.0490 (5)C7 0.8883 (2) 0.0937 (4) 0.53638 (13) 0.0621 (7)C8 0.8062 (2) 0.0598 (5) 0.45769 (15) 0.0835 (9)C9 0.6918 (3) 0.2064 (6) 0.42996 (16) 0.1048 (12)C10 0.6579 (3) 0.3796 (6) 0.48092 (14) 0.0923 (9)C11 0.73748 (19) 0.4136 (4) 0.56322 (11) 0.0569 (6)C12 0.98242 (16) 0.5453 (3) 0.80117 (9) 0.0413 (5)C13 1.00197 (18) 0.4050 (3) 0.87253 (10) 0.0487 (5)C14 1.09842 (19) 0.4651 (4) 0.94460 (12) 0.0591 (6)C15 1.1735 (2) 0.6638 (4) 0.94456 (12) 0.0608 (7)C16 1.15312 (19) 0.8023 (3) 0.87348 (13) 0.0588 (6)C17 1.05718 (18) 0.7432 (3) 0.80046 (11) 0.0490 (5)C18 0.69538 (15) 0.7673 (3) 0.75203 (10) 0.0423 (5)C19 0.67842 (17) 0.7258 (3) 0.84001 (10) 0.0484 (5)C20 0.59554 (18) 0.8651 (3) 0.88969 (11) 0.0526 (6)C21 0.53344 (17) 1.0466 (3) 0.84817 (11) 0.0476 (5)C22 0.55001 (18) 1.0905 (3) 0.76149 (11) 0.0490 (5)C23 0.62930 (17) 0.9549 (3) 0.71145 (10) 0.0471 (5)C25 0.3916 (2) 1.3373 (4) 0.80727 (13) 0.0644 (7)H7 0.96700 −0.00050 0.55440 0.0750*H8 0.82650 −0.06040 0.42280 0.1000*H9 0.63780 0.18510 0.37560 0.1260*H10 0.58160 0.47610 0.46110 0.1110*H13 0.95090 0.27130 0.87220 0.0580*H14 1.11260 0.37170 0.99310 0.0710*H15 1.23820 0.70390 0.99310 0.0730*H16 1.20370 0.93640 0.87410 0.0710*H17 1.04380 0.83620 0.75180 0.0590*H19 0.72360 0.60150 0.86660 0.0580*H20 0.58330 0.83540 0.94840 0.0630*H23A 0.28690 1.30300 0.79170 0.0770*H23B 0.40020 1.49370 0.82050 0.0770*H26 0.63900 0.98610 0.65250 0.0570*Atomic displacement parameters (Å2) U11 U22 U33 U12 U13 U23O5 0.0584 (7) 0.0551 (7) 0.0635 (7) 0.0186 (6) 0.0045 (6) 0.0065 (6)O24 0.0545 (7) 0.0728 (9) 0.0645 (7) 0.0097 (7) 0.0101 (6) −0.0164 (7)O26 0.0705 (9) 0.0601 (8) 0.0795 (8) 0.0209 (7) 0.0228 (7) 0.0092 (7)N1 0.0408 (7) 0.0766 (11) 0.0470 (7) 0.0126 (8) −0.0016 (6) −0.0096 (8)N3 0.0370 (6) 0.0445 (7) 0.0430 (6) 0.0033 (6) 0.0025 (5) 0.0029 (6)C2 0.0338 (7) 0.0526 (10) 0.0441 (8) 0.0033 (7) 0.0035 (6) 0.0023 (7)C4 0.0430 (8) 0.0414 (9) 0.0497 (9) 0.0006 (7) 0.0105 (7) 0.0053 (7)C6 0.0392 (8) 0.0560 (11) 0.0533 (9) −0.0022 (8) 0.0125 (7) −0.0040 (8)C7 0.0522 (10) 0.0674 (13) 0.0688 (11) −0.0017 (9) 0.0163 (9) −0.0163 (10)C8 0.0590 (12) 0.108 (2) 0.0847 (14) 0.0021 (14) 0.0134 (11) −0.0491 (15)supporting informationsup-5Acta Cryst. (2013). E69, o1113    C9 0.0626 (13) 0.169 (3) 0.0792 (14) 0.0229 (17) −0.0125 (11) −0.0633 (17)C10 0.0616 (12) 0.142 (2) 0.0694 (13) 0.0328 (15) −0.0145 (10) −0.0415 (15)C11 0.0403 (8) 0.0769 (13) 0.0534 (9) 0.0035 (9) 0.0033 (7) −0.0150 (9)C12 0.0325 (7) 0.0455 (9) 0.0458 (8) 0.0052 (7) 0.0040 (6) 0.0019 (7)C13 0.0408 (8) 0.0539 (10) 0.0514 (9) 0.0014 (8) 0.0039 (6) 0.0096 (8)C14 0.0481 (9) 0.0804 (14) 0.0480 (9) 0.0125 (10) 0.0005 (7) 0.0101 (9)C15 0.0433 (9) 0.0767 (15) 0.0607 (11) 0.0098 (9) −0.0041 (8) −0.0119 (10)C16 0.0437 (9) 0.0525 (10) 0.0799 (12) −0.0023 (9) 0.0036 (8) −0.0120 (10)C17 0.0425 (8) 0.0440 (9) 0.0601 (10) 0.0036 (7) 0.0026 (7) 0.0071 (8)C18 0.0303 (7) 0.0518 (9) 0.0444 (8) 0.0002 (7) 0.0013 (6) −0.0016 (7)C19 0.0390 (8) 0.0597 (10) 0.0458 (8) 0.0077 (8) 0.0001 (6) 0.0028 (8)C20 0.0425 (8) 0.0740 (13) 0.0413 (8) 0.0036 (9) 0.0035 (6) −0.0016 (8)C21 0.0345 (7) 0.0593 (11) 0.0487 (8) −0.0016 (7) 0.0031 (6) −0.0131 (8)C22 0.0395 (8) 0.0478 (9) 0.0599 (10) 0.0020 (8) 0.0064 (7) −0.0001 (8)C23 0.0395 (8) 0.0580 (10) 0.0443 (8) 0.0009 (8) 0.0063 (6) 0.0022 (8)C25 0.0517 (10) 0.0643 (12) 0.0785 (12) 0.0096 (9) 0.0130 (9) −0.0074 (10)Geometric parameters (Å, º) O5—C4 1.225 (2) C15—C16 1.369 (3)O24—C21 1.381 (2) C16—C17 1.390 (3)O24—C25 1.427 (3) C18—C19 1.387 (2)O26—C22 1.375 (2) C18—C23 1.399 (3)O26—C25 1.423 (2) C19—C20 1.395 (2)N1—C2 1.285 (2) C20—C21 1.362 (3)N1—C11 1.383 (3) C21—C22 1.370 (2)N3—C2 1.399 (2) C22—C23 1.366 (2)N3—C4 1.406 (2) C7—H7 0.9300N3—C12 1.443 (2) C8—H8 0.9300C2—C18 1.485 (2) C9—H9 0.9300C4—C6 1.449 (2) C10—H10 0.9300C6—C7 1.395 (3) C13—H13 0.9300C6—C11 1.391 (3) C14—H14 0.9300C7—C8 1.364 (3) C15—H15 0.9300C8—C9 1.394 (4) C16—H16 0.9300C9—C10 1.357 (5) C17—H17 0.9300C10—C11 1.400 (3) C19—H19 0.9300C12—C13 1.379 (2) C20—H20 0.9300C12—C17 1.374 (3) C23—H26 0.9300C13—C14 1.383 (3) C25—H23A 0.9700C14—C15 1.380 (3) C25—H23B 0.9700C21—O24—C25 105.01 (14) O24—C21—C22 109.49 (15)C22—O26—C25 105.05 (14) C20—C21—C22 121.91 (16)C2—N1—C11 118.47 (15) O26—C22—C21 110.03 (15)C2—N3—C4 121.26 (13) O26—C22—C23 127.86 (15)C2—N3—C12 121.91 (13) C21—C22—C23 122.12 (16)C4—N3—C12 116.04 (12) C18—C23—C22 117.59 (14)supporting informationsup-6Acta Cryst. (2013). E69, o1113    N1—C2—N3 123.30 (15) O24—C25—O26 107.75 (16)N1—C2—C18 116.16 (14) C6—C7—H7 120.00N3—C2—C18 120.49 (13) C8—C7—H7 120.00O5—C4—N3 120.30 (14) C7—C8—H8 120.00O5—C4—C6 124.52 (16) C9—C8—H8 120.00N3—C4—C6 115.17 (14) C8—C9—H9 119.00C4—C6—C7 120.76 (16) C10—C9—H9 119.00C4—C6—C11 118.60 (16) C9—C10—H10 120.00C7—C6—C11 120.64 (16) C11—C10—H10 120.00C6—C7—C8 119.9 (2) C12—C13—H13 120.00C7—C8—C9 119.6 (2) C14—C13—H13 120.00C8—C9—C10 121.2 (2) C13—C14—H14 120.00C9—C10—C11 120.3 (3) C15—C14—H14 120.00N1—C11—C6 122.83 (15) C14—C15—H15 120.00N1—C11—C10 118.6 (2) C16—C15—H15 120.00C6—C11—C10 118.4 (2) C15—C16—H16 120.00N3—C12—C13 119.83 (15) C17—C16—H16 120.00N3—C12—C17 118.99 (14) C12—C17—H17 120.00C13—C12—C17 121.15 (14) C16—C17—H17 120.00C12—C13—C14 119.28 (17) C18—C19—H19 119.00C13—C14—C15 119.95 (18) C20—C19—H19 119.00C14—C15—C16 120.36 (17) C19—C20—H20 122.00C15—C16—C17 120.23 (17) C21—C20—H20 122.00C12—C17—C16 119.03 (16) C18—C23—H26 121.00C2—C18—C19 123.05 (16) C22—C23—H26 121.00C2—C18—C23 116.63 (14) O24—C25—H23A 110.00C19—C18—C23 119.63 (15) O24—C25—H23B 110.00C18—C19—C20 121.88 (16) O26—C25—H23A 110.00C19—C20—C21 116.88 (15) O26—C25—H23B 110.00O24—C21—C20 128.60 (15) H23A—C25—H23B 108.00C25—O24—C21—C20 −170.35 (18) C11—C6—C7—C8 −0.6 (3)C25—O24—C21—C22 9.67 (19) C4—C6—C11—N1 −5.3 (3)C21—O24—C25—O26 −15.83 (19) C4—C6—C11—C10 178.3 (2)C25—O26—C22—C21 −10.09 (19) C7—C6—C11—N1 175.08 (18)C25—O26—C22—C23 170.00 (18) C7—C6—C11—C10 −1.4 (3)C22—O26—C25—O24 15.97 (19) C6—C7—C8—C9 2.2 (3)C11—N1—C2—N3 4.8 (3) C7—C8—C9—C10 −1.7 (4)C11—N1—C2—C18 −172.49 (16) C8—C9—C10—C11 −0.4 (4)C2—N1—C11—C6 0.3 (3) C9—C10—C11—N1 −174.8 (2)C2—N1—C11—C10 176.7 (2) C9—C10—C11—C6 1.9 (4)C4—N3—C2—N1 −4.8 (2) N3—C12—C13—C14 177.68 (15)C4—N3—C2—C18 172.43 (14) C17—C12—C13—C14 0.1 (3)C12—N3—C2—N1 164.67 (16) N3—C12—C17—C16 −178.07 (15)C12—N3—C2—C18 −18.1 (2) C13—C12—C17—C16 −0.5 (2)C2—N3—C4—O5 178.13 (15) C12—C13—C14—C15 0.1 (3)C2—N3—C4—C6 −0.4 (2) C13—C14—C15—C16 0.0 (3)C12—N3—C4—O5 8.1 (2) C14—C15—C16—C17 −0.4 (3)supporting informationsup-7Acta Cryst. (2013). E69, o1113    C12—N3—C4—C6 −170.47 (14) C15—C16—C17—C12 0.6 (3)C2—N3—C12—C13 120.18 (17) C2—C18—C19—C20 −169.50 (15)C2—N3—C12—C17 −62.2 (2) C23—C18—C19—C20 0.7 (2)C4—N3—C12—C13 −69.84 (18) C2—C18—C23—C22 170.86 (14)C4—N3—C12—C17 107.81 (17) C19—C18—C23—C22 0.1 (2)N1—C2—C18—C19 135.61 (17) C18—C19—C20—C21 −1.0 (2)N1—C2—C18—C23 −34.8 (2) C19—C20—C21—O24 −179.44 (16)N3—C2—C18—C19 −41.8 (2) C19—C20—C21—C22 0.5 (2)N3—C2—C18—C23 147.76 (15) O24—C21—C22—O26 0.25 (19)O5—C4—C6—C7 6.2 (3) O24—C21—C22—C23 −179.83 (16)O5—C4—C6—C11 −173.46 (17) C20—C21—C22—O26 −179.74 (15)N3—C4—C6—C7 −175.32 (16) C20—C21—C22—C23 0.2 (3)N3—C4—C6—C11 5.0 (2) O26—C22—C23—C18 179.41 (16)C4—C6—C7—C8 179.72 (19) C21—C22—C23—C18 −0.5 (2)Hydrogen-bond geometry (Å, º) D—H···A D—H H···A D···A D—H···AC17—H17···O5i 0.93 2.37 3.185 (3) 146C25—H23A···O5ii 0.97 2.49 3.416 (3) 160Symmetry codes: (i) x, y+1, z; (ii) x−1, y+1, z.

Acta Crystallographica Section E Structure Reports Online

2-(1,3-Benzodioxol-5-yl)-3-phenylquinazolin-4(3<i>H</i>)-one

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2-(1,3-Benzodioxol-5-yl)-3-phenylquinazolin-4(3
                    H

2-(1,3-Benzodioxol-5-yl)-3-phenylquinazolin-4(3 H

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