2-Methyl-3-(2-methyl­phen­yl)-4-oxo-3,4-dihydro­quinazolin-8-yl 4-methyl­benzoate

Adel S El-Azab; Alaa A-M Abdel-Aziz; Seik Weng Ng; Edward R T Tiekink

doi:10.1107/S1600536812006265

. 2012 Feb 17;68(Pt 3):o734–o735. doi: 10.1107/S1600536812006265

2-Methyl-3-(2-methylphenyl)-4-oxo-3,4-dihydroquinazolin-8-yl 4-methylbenzoate

Adel S El-Azab ^a,^b,^‡, Alaa A-M Abdel-Aziz ^a,^c, Seik Weng Ng ^d,^e, Edward R T Tiekink ^d,^*

PMCID: PMC3295504 PMID: 22412615

Abstract

In the title quinazolin-4-one derivative, C₂₄H₂₀N₂O₃, both the 4-methylbenzoate [dihedral angle = 83.90 (9)°] and 2-tolyl [87.88 (9)°] groups are almost orthogonal to the central fused ring system. These aryl groups are oriented towards the quinazolin-4-one-bound methyl group. In the crystal, molecules are connected into a three-dimensional architecture by C—H⋯O, C—H⋯π and π–π [ring centroid-to-centroid separation = 3.6458 (13) Å] interactions.

Related literature

For the pharmacological activity of substituted quinazoline-4(3H)-ones, see: El-Azab & ElTahir (2012 ▶); El-Azab et al. (2011 ▶); Al-Omary et al. (2010 ▶); Al-Obaid et al. (2009 ▶); Aziza et al. (1996 ▶). For the synthesis and evaluation of the anticonvulsant activity of the title compound, see: El-Azab et al. (2010 ▶). For the structure of the benzoate derivative, see: El-Azab et al. (2012 ▶).

Experimental

Crystal data

C₂₄H₂₀N₂O₃
M _r = 384.42
Monoclinic,
a = 18.8216 (5) Å
b = 7.6332 (2) Å
c = 13.3092 (3) Å
β = 97.286 (2)°
V = 1896.68 (8) Å³
Z = 4
Cu Kα radiation
μ = 0.72 mm⁻¹
T = 100 K
0.25 × 0.20 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T _min = 0.755, T _max = 1.000
7966 measured reflections
3883 independent reflections
3478 reflections with I > 2σ(I)
R _int = 0.027

Refinement

R[F ² > 2σ(F ²)] = 0.067
wR(F ²) = 0.186
S = 1.06
3883 reflections
265 parameters
H-atom parameters constrained
Δρ_max = 1.09 e Å⁻³
Δρ_min = −0.33 e Å⁻³

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 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Supplementary Material

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812006265/hb6636sup1.cif

e-68-0o734-sup1.cif^{(21.9KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006265/hb6636Isup2.hkl

e-68-0o734-Isup2.hkl^{(190.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812006265/hb6636Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of the C18–C23 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C17—H17C⋯O2ⁱ	0.98	2.55	3.434 (3)	150
C21—H21⋯O3ⁱⁱ	0.95	2.47	3.299 (3)	146
C12—H12⋯Cg1ⁱⁱⁱ	0.95	2.79	3.658 (2)	153

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

This work was supported by the Research Center of Pharmacy, King Saud University, Riyadh, Saudi Arabia. We also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research Scheme (grant No. UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

The title compound, (I), a methaqualone analogue, was recently synthesized and evaluated for its anti-convulsant activity (El-Azab et al., 2010). Herein, the crystal structure determination of 3,4-dihydro-2-methyl-3-(2-methylphenyl)-4-oxoquinazolin-8-yl 4-methylbenzoate (I) is reported. These studies were motivated by the observation that substituted quinazoline-4(3H)-ones are known to display various biological activities (El-Azab & ElTahir, 2012; El-Azab et al., 2011; El-Azab et al., 2010; Al-Omary et al., 2010; Al-Obaid et al., 2009; Aziza et al., 1996).

In (I), Fig. 1, the carboxylate residue is co-planar to the benzene ring to which it is connected as seen in the value of the C2—C1—C8—O1 torsion angle -3.8 (3)°. With respect to the central quinazolin-4-one fused ring system [r.m.s. deviation = 0.045 Å for the 10 atoms], both the 4-methylbenzoate and 2-tolyl groups are orthogonal: the dihedral angles between the central plane and six-membered rings being 83.90 (9) and 87.88 (9)°, respectively. Both aryl substituents are orientated towards the methyl group bound to the quinazolin-4-one system and the dihedral angle between the two six-membered rings is 77.04 (11)°. The molecular structure resembles closely that of the benzoate derivative (El-Azab et al., 2012).

In the crystal packing, C—H···O [involving both carbonyl-O atoms] and C—H···π [involving the (C18···C23) benzene ring] interactions, Table 1, lead to the formation of layers in the bc plane. These interdigitate to allow for the formation of π–π interactions between the 4-methylbenzoate rings [ring centroid···centroid separation = 3.6458 (13) Å between centrosymmetrically related (C1–C6) rings; symmetry operation: 1 - x, 2 - y, 1 - z]. The combination of intermolecular interactions leads to a three-dimensional architecture, Fig. 2.

Experimental

A mixture of 8-hydroxymethaqualone (532 mg, 0.002 M) and 4-methylbenzoyl chloride (325 mg, 0.0021 mmol) in 15 ml pyridine was stirred at room temperature for 12 h. The solvent was removed under reduced pressure, and the residue was triturated with water and filtered. The solid obtained was dried and recrystallized from EtOH to yield colourless prisms. m.p. 465–467 K. Yield: 95%. ¹H NMR (500 MHz, CDCl₃): δ = 8.25–8.22 (m, 3H), 7.64 (d, 1H, J = 7.5 Hz), 7.52 (t, 1H, J = 7.5 Hz), 7.43–7.28 (m, 5H), 7.15 (d, 1H, J = 7.5 Hz), 2.49 (s, 3H), 2.15 (s, 3H), 2.11 (s, 3H) p.p.m.. ¹³C NMR (CDCl₃): δ = 17.4, 21.8, 24.3, 120.7, 124.9, 126.4, 126.7, 127.4, 127.6, 127.9, 129.3, 129.6, 130.5, 131.5, 135.4, 136.8, 141.0, 144.5, 146.3, 154.7, 161.2, 165.3 p.p.m.. MS (70 eV): m/z = 384.