Experimental. Crystal data. C 23 H 20 N 2 O 2 M r = Monoclinic, P2 1 =c a = (3) Å b = (1) Å c = (2) Å = 91.

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1 organic compounds Acta Crystallographica Section E Structure Reports Online ISSN Benzyloxy-2-methyl-3-(2-methylphenyl)quinazolin-4(3H)-one Adel S. El-Azab, a,b Alaa A.-M. Abdel-Aziz, a,c Seik Weng Ng d,e and Edward R. T. Tiekink d * a Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, b Department of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt, c Department of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, d Department of Chemistry, University of Malaya, Kuala Lumpur, Malaysia, and e Chemistry Department, Faculty of Science, King Abdulaziz University, PO Box Jeddah, Saudi Arabia Correspondence edward.tiekink@gmail.com Received 18 February 2012; accepted 18 February 2012 Key indicators: single-crystal X-ray study; T = 100 K; mean (C C) = Å; disorder in main residue; R factor = 0.048; wr factor = 0.121; data-to-parameter ratio = In the title methaqualone analogue, C 23 H 20 N 2 O 2, the planes of the terminal aromatic rings [dihedral angle between them = (7) ] approximately face the fused-ring methyl group and both are twisted with respect to the pyrimidine plane (r.m.s. deviation = Å), forming dihedral angles of 86.9 (3) (with the 2-tolyl ring) and (7). The 2-tolyl residue is disordered over two almost coplanar but opposite orientations with the major component having a siteoccupancy factor of (3). The three-dimensional crystal packing is consolidated by C HO, C H and [2- tolyl 2-tolyl centroid centroid distance = (6) Å] interactions. Related literature For recent studies on the synthesis, drug discovery and crystal structures of quinazoline-4(3h)-one derivatives, see: El-Azab et al. (2010, 2012). For the anti-convulsant activity of the title methaqualone analogue, see: El-Azab et al. (2011). For a related structure, see: Stephenson et al. (2011). Experimental Crystal data C 23 H 20 N 2 O 2 M r = Monoclinic, P2 1 =c a = (3) Å b = (1) Å c = (2) Å = (2) Data collection Agilent SuperNova Dual diffractometer with an Atlas detector Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) T min = 0.967, T max = Refinement R[F 2 >2(F 2 )] = wr(f 2 ) = S = reflections 245 parameters Table 1 Hydrogen-bond geometry (Å, ). Cg1 is the centroid of the C18 C23 ring. V = (5) Å 3 Z =4 Cu K radiation = 0.66 mm 1 T = 100 K mm 7568 measured reflections 3775 independent reflections 3559 reflections with I > 2(I) R int = restraints H-atom parameters constrained max = 0.44 e Å 3 min = 0.39 e Å 3 D HA D H HA DA D HA C13 H13O1 i (15) 140 C17 H17BCg1 ii (16) 150 C22 H22Cg1 iii (16) 143 Symmetry codes: (i) x þ 2; y þ 2; z þ 1; (ii) x þ 1; y; z þ 1; (iii) x þ 1; y 1 2 ; z þ 1 2. Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); Additional correspondence author, adelazaba@yahoo.com. o864 El-Azab et al. doi: /s

2 organic compounds software used to prepare material for publication: publcif (Westrip, 2010). This work was supported by the Research Center of Pharmacy, King Saud University, Riyadh, Saudi Arabia. The authors also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High- Impact Research scheme (grant No. UMC/HIR/MOHE/SC/ 12). Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6643). References Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. El-Azab, A. S., Al-Omar, M. A., Abdel-Aziz, A. A.-M., Abdel-Aziz, N. I., El- Sayed, M. A.-A., Aleisa, A. M., Sayed-Ahmed, M. M. & Abdel-Hamide, S. G. (2010). Eur. J. Med. Chem. 45, El-Azab, A. S. & ElTahir, K. H. (2012). Bioorg. Med. Chem. Lett. 22, El-Azab, A. S., ElTahir, K. H. & Attia, S. M. (2011). Monatsh. Chem. 142, Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. Sheldrick, G. M. (2008). Acta Cryst. A64, Stephenson, K. A., Wilson, A. A., Houle, S. & Vasdev, N. (2011). Bioorg. Med. Chem. Lett. 21, Westrip, S. P. (2010). J. Appl. Cryst. 43, El-Azab et al. C 23 H 20 N 2 O 2 o865

3 supplementary materials [doi: /s ] 8-Benzyloxy-2-methyl-3-(2-methylphenyl)quinazolin-4(3H)-one Adel S. El-Azab, Alaa A.-M. Abdel-Aziz, Seik Weng Ng and Edward R. T. Tiekink Comment Quinazoline-4(3H)-one derivatives are known for their various biological activities (El-Azab et al., 2012, 2010). The title methaqualone analogue, 8-benzyloxy-2-methyl-3-(2-methylphenyl)-4(3H)-quinazolinone (I), has been investigated previously for its anti-convulsant activity (El-Azab et al., 2011). Herein, its crystal and molecular structure is described. A related structure with a similar conformation has been reported recently (Stephenson et al., 2011). In (I), Fig. 1, the 2-tolyl group is orthogonal to the pyrimidine ring [r.m.s. deviation = Å] forming a dihedral angle of (6) ; the equivalent angle for the minor component of the disordered 2-tolyl ring = 86.9 (3). The phenyl ring of the benzyloxy residue is also twisted out of this plane, forming a dihedral angle of (7). To a first approximation the planes through the terminal rings face towards the methyl group with the dihedral angle between them being (7). In the crystal packing, C H O and C H π interactions, Table 1, combine with π π [ring centroid(2-tolyl)-tocentroid(2-tolyl) i distance = (6) Å for symmetry operation i: 2 - x, 2 - y, 1 - z] interactions to consolidate molecules into the three-dimensional architecture, Fig. 2. Experimental A mixture of 8-hydroxymethaqualone (532 mg, 2 mmol) and benzyl chloride (266 mg, 2.1 mmol) in acetone (15 ml) containing anhydrous potassium carbonate (415 mg, 3 mmol) was heated under reflux for 10 h. The reaction mixture was filtered while hot, the solvent was removed under reduced pressure, and the solid obtained was dried and recrystallized from AcOH as colourless prisms. Yield 86%; M.pt: K. 1 H NMR (500 MHz, CDCl 3 ): δ 7.89 (d, 1H, J = 8.0 Hz), 7.53 (d, 2H, J = 7.0 Hz), (m, 7H), 7.22 (d, 1H, J = 8.0 Hz), 7.17 (d, 1H, J = 7.5 Hz), 5.40 (s, 2H), 2.27 (s, 3H), 2.15 (s, 3H). 13 C NMR (CDCl 3 ): δ 17.4, 24.3, 71.3, 117.1, 119.0, 122.1, 126.6, 127.0, 127.6, 127.9, 128.0, 128.6, 129.5, 131.5, 135.3, 136.8, 137.0, 138.8, 153.3, 153.6, p.p.m.. MS (70 ev): m/z = 356. Refinement Carbon-bound H-atoms were placed in calculated positions [C H = 0.95 to 0.99 Å, U iso (H) = 1.2 to 1.5U eq (C)] and were included in the refinement in the riding model approximation. The 2-tolyl ring is disordered over two co-planar positions with the methyl group being orientated in opposite directions. The benzene rings were refined as rigid hexagons with C C = 1.39 Å. The major component refined to a site occupancy factor of (3). The C C distances were restrained to ±0.01 Å, of each other. The anisotropic displacement parameters were restrained to be nearly isotropic, and those of the primed carbon atoms were equated to those of unprimed atoms. Computing details Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, sup-1

4 2006); software used to prepare material for publication: publcif (Westrip, 2010). Figure 1 The molecular structure of (I) showing displacement ellipsoids at the 50% probability level. The minor disorder component of the toluyl ring is not shown. sup-2

5 Figure 2 A view in projection down the b axis of the unit-cell contents of (I). The C H O, C H π and π π interactions are shown as orange, bronw and purple dashed lines, respectively. 8-Benzyloxy-2-methyl-3-(2-methylphenyl)quinazolin-4(3H)-one Crystal data C 23 H 20 N 2 O 2 M r = Monoclinic, P2 1 /c Hall symbol: -P 2ybc a = (3) Å b = (1) Å c = (2) Å β = (2) V = (5) Å 3 Z = 4 Data collection Agilent SuperNova Dual diffractometer with an Atlas detector Radiation source: SuperNova (Cu) X-ray Source Mirror monochromator Detector resolution: pixels mm -1 ω scan Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011) Refinement Refinement on F 2 Least-squares matrix: full R[F 2 > 2σ(F 2 )] = wr(f 2 ) = S = reflections F(000) = 752 D x = Mg m 3 Cu Kα radiation, λ = Å Cell parameters from 4269 reflections θ = µ = 0.66 mm 1 T = 100 K Prism, colourless mm T min = 0.967, T max = measured reflections 3775 independent reflections 3559 reflections with I > 2σ(I) R int = θ max = 76.5, θ min = 4.8 h = k = 9 9 l = parameters 43 restraints Primary atom site location: structure-invariant direct methods Secondary atom site location: difference Fourier map sup-3

6 Hydrogen site location: inferred from neighbouring sites H-atom parameters constrained w = 1/[σ 2 (F o2 ) + (0.0589P) P] where P = (F o 2 + 2F c2 )/3 (Δ/σ) max < Δρ max = 0.44 e Å 3 Δρ min = 0.39 e Å 3 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 F 2 against ALL reflections. The weighted R-factor wr and goodness of fit S are based on F 2, conventional R-factors R are based on F, with F set to zero for negative F 2. The threshold expression of F 2 > σ(f 2 ) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F 2 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 (Å 2 ) x y z U iso */U eq Occ. (<1) O (6) (15) (8) (3) O (5) (14) (7) (2) N (7) (18) (9) (3) N (6) (16) (9) (3) C (8) (19) (10) (3) C (7) (18) (10) (3) C (8) (19) (11) (3) H * C (8) (2) (11) (3) H * C (8) (19) (11) (3) H * C (8) (18) (10) (3) C (7) (18) (10) (3) C (8) (2) (11) (3) C (9) (3) (11) (4) H9A * H9B * H9C * C (5) (12) (8) (4) (3) C (6) (11) (9) (4) (3) H * (3) C (5) (15) (9) (4) (3) H * (3) C (5) (14) (9) (4) (3) H * (3) C (6) (10) (9) (4) (3) H * (3) C (5) (14) (8) (4) (3) C (10) (2) (14) (4) (3) H16A * (3) H16B * (3) sup-4

7 H16C * (3) C (5) (10) (7) (4) (3) C (4) (12) (7) (4) (3) H * (3) C (5) (9) (8) (4) (3) H * (3) C (5) (10) (8) (4) (3) H * (3) C (4) (13) (8) (4) (3) H * (3) C (5) (10) (7) (4) (3) C (12) (3) (16) (4) (3) H16D * (3) H16E * (3) H16F * (3) C (8) (2) (11) (3) H17A * H17B * C (8) (18) (11) (3) C (8) (19) (11) (3) H * C (8) (2) (12) (3) H * C (8) (2) (11) (3) H * C (8) (2) (11) (3) H * C (8) (19) (11) (3) H * Atomic displacement parameters (Å 2 ) U 11 U 22 U 33 U 12 U 13 U 23 O (5) (6) (5) (4) (4) (4) O (5) (5) (5) (4) (4) (4) N (6) (7) (6) (5) (5) (5) N (6) (6) (5) (5) (4) (5) C (6) (7) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) C (7) (7) (7) (6) (5) (5) C (8) (7) (6) (6) (6) (6) C (7) (7) (7) (6) (6) (5) C (7) (6) (6) (5) (5) (5) C (6) (6) (6) (5) (5) (5) C (7) (7) (7) (6) (5) (5) C (8) (10) (7) (7) (6) (7) C (8) (9) (7) (6) (6) (6) C (9) (11) (8) (8) (6) (8) C (8) (11) (8) (7) (6) (7) C (9) (11) (8) (8) (6) (7) sup-5

8 C (9) (9) (8) (7) (6) (7) C (8) (8) (7) (7) (6) (6) C (9) (9) (9) (7) (7) (7) C (8) (9) (7) (6) (6) (6) C (9) (11) (8) (8) (6) (8) C (8) (11) (8) (7) (6) (7) C (9) (11) (8) (8) (6) (7) C (9) (9) (8) (7) (6) (7) C (8) (8) (7) (7) (6) (6) C (9) (9) (9) (7) (7) (7) C (7) (7) (7) (6) (5) (6) C (7) (6) (7) (5) (5) (5) C (7) (7) (7) (6) (6) (6) C (7) (7) (8) (6) (6) (6) C (7) (7) (7) (6) (6) (6) C (7) (7) (7) (6) (6) (6) C (6) (7) (7) (5) (5) (6) Geometric parameters (Å, º) O1 C (18) C15 C (19) O2 C (17) C16 H16A O2 C (16) C16 H16B N1 C (18) C16 H16C N1 C (18) C10 C N1 C (14) C10 C N1 C (6) C11 C N2 C (19) C11 H N2 C (17) C12 C C1 C (19) C12 H C2 C (19) C13 C C2 C (19) C13 H C3 C (2) C14 C C3 H C14 H C4 C (2) C15 C (19) C4 H C16 H16D C5 C (2) C16 H16E C5 H C16 H16F C6 C (19) C17 C (2) C8 C (2) C17 H17A C9 H9A C17 H17B C9 H9B C18 C (2) C9 H9C C18 C (2) C10 C C19 C (2) C10 C C19 H C11 C C20 C (2) C11 H C20 H C12 C C21 C (2) C12 H C21 H C13 C C22 C (2) sup-6

9 C13 H C22 H C14 C C23 H C14 H C6 O2 C (11) C15 C14 H C8 N1 C (12) C14 C15 C C8 N1 C (11) C14 C15 C (10) C1 N1 C (11) C10 C15 C (10) C8 N1 C (4) C11 C10 C C1 N1 C (4) C11 C10 N (6) C10 N1 C (3) C15 C10 N (6) C8 N2 C (12) C12 C11 C O1 C1 N (13) C12 C11 H O1 C1 C (13) C10 C11 H N1 C1 C (12) C11 C12 C C7 C2 C (13) C11 C12 H C7 C2 C (12) C13 C12 H C3 C2 C (13) C14 C13 C C4 C3 C (13) C14 C13 H C4 C3 H C12 C13 H C2 C3 H C13 C14 C C3 C4 C (13) C13 C14 H C3 C4 H C15 C14 H C5 C4 H C14 C15 C C6 C5 C (13) C14 C15 C (11) C6 C5 H C10 C15 C (11) C4 C5 H C15 C16 H16D O2 C6 C (13) C15 C16 H16E O2 C6 C (12) H16D C16 H16E C5 C6 C (13) C15 C16 H16F N2 C7 C (12) H16D C16 H16F N2 C7 C (12) H16E C16 H16F C2 C7 C (12) O2 C17 C (11) N2 C8 N (13) O2 C17 H17A N2 C8 C (13) C18 C17 H17A N1 C8 C (13) O2 C17 H17B C8 C9 H9A C18 C17 H17B C8 C9 H9B H17A C17 H17B H9A C9 H9B C19 C18 C (14) C8 C9 H9C C19 C18 C (13) H9A C9 H9C C23 C18 C (13) H9B C9 H9C C18 C19 C (14) C11 C10 C C18 C19 H C11 C10 N (9) C20 C19 H C15 C10 N (9) C21 C20 C (14) C10 C11 C C21 C20 H C10 C11 H C19 C20 H C12 C11 H C20 C21 C (14) C11 C12 C C20 C21 H sup-7

10 C11 C12 H C22 C21 H C13 C12 H C23 C22 C (14) C14 C13 C C23 C22 H C14 C13 H C21 C22 H C12 C13 H C22 C23 C (13) C13 C14 C C22 C23 H C13 C14 H C18 C23 H C8 N1 C1 O (14) C10 N1 C10 C (8) C10 N1 C1 O1 4.3 (2) C15 C10 C11 C C10 N1 C1 O (4) N1 C10 C11 C (11) C8 N1 C1 C2 0.5 (2) C10 C11 C12 C C10 N1 C1 C (11) C11 C12 C13 C C10 N1 C1 C (4) C12 C13 C14 C O1 C1 C2 C (14) C13 C14 C15 C N1 C1 C2 C (19) C13 C14 C15 C (11) O1 C1 C2 C3 1.8 (2) C11 C10 C15 C N1 C1 C2 C (13) N1 C10 C15 C (10) C7 C2 C3 C4 1.3 (2) C11 C10 C15 C (11) C1 C2 C3 C (13) N1 C10 C15 C (13) C2 C3 C4 C5 0.5 (2) C8 N1 C10 C (7) C3 C4 C5 C6 1.1 (2) C1 N1 C10 C (7) C17 O2 C6 C5 0.3 (2) C10 N1 C10 C (13) C17 O2 C6 C (12) C8 N1 C10 C (5) C4 C5 C6 O (13) C1 N1 C10 C (5) C4 C5 C6 C7 0.0 (2) C10 N1 C10 C (5) C8 N2 C7 C2 3.1 (2) C15 C10 C11 C C8 N2 C7 C (13) N1 C10 C11 C (9) C3 C2 C7 N (13) C10 C11 C12 C C1 C2 C7 N2 5.9 (2) C11 C12 C13 C C3 C2 C7 C6 2.3 (2) C12 C13 C14 C C1 C2 C7 C (12) C13 C14 C15 C O2 C6 C7 N (19) C13 C14 C15 C (13) C5 C6 C7 N (13) C11 C10 C15 C O2 C6 C7 C (12) N1 C10 C15 C (7) C5 C6 C7 C2 1.7 (2) C11 C10 C15 C (13) C7 N2 C8 N1 1.7 (2) N1 C10 C15 C (12) C7 N2 C8 C (14) C6 O2 C17 C (12) C1 N1 C8 N2 3.5 (2) O2 C17 C18 C (14) C10 N1 C8 N (13) O2 C17 C18 C (17) C10 N1 C8 N (4) C23 C18 C19 C (2) C1 N1 C8 C (14) C17 C18 C19 C (13) C10 N1 C8 C9 9.0 (2) C18 C19 C20 C (2) C10 N1 C8 C (4) C19 C20 C21 C (2) C8 N1 C10 C (14) C20 C21 C22 C (2) C1 N1 C10 C (13) C21 C22 C23 C (2) C10 N1 C10 C (8) C19 C18 C23 C (2) C8 N1 C10 C (14) C17 C18 C23 C (13) C1 N1 C10 C (13) sup-8

11 Hydrogen-bond geometry (Å, º) D H A D H H A D A D H A C13 H13 O1 i (15) 140 C17 H17B Cg1 ii (16) 150 C22 H22 Cg1 iii (16) 143 Symmetry codes: (i) x+2, y+2, z+1; (ii) x+1, y, z+1; (iii) x+1, y 1/2, z+1/2. sup-9