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

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

doi:10.1107/S1600536812025147

. 2012 Jun 13;68(Pt 7):o2052–o2053. doi: 10.1107/S1600536812025147

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

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

PMCID: PMC3393320 PMID: 22807877

Abstract

In the title compound, C₂₃H₁₇ClN₂O₃, the quinazoline fused-ring system, including the ring-bound carbonyl-O and methyl-C atoms, is close to being planar (r.m.s. deviation = 0.044 Å) and is essentially orthogonal to both the 2-tolyl ring [dihedral angle = 89.51 (8)°] and to the ester group [the C—O—C—C torsion angle = −103.69 (16)°]. The carboxylate group is almost coplanar with the benzene ring to which it is attached [O—C—C—C torsion angle = −4.7 (2)°]. The 2-tolyl ring system is disordered over two orientations in a 0.871 (3):0.129 (3) ratio. In the crystal, molecules are consolidated into a three-dimensional architecture by C—H⋯Cl, C—H⋯O, C—H⋯N, C—H⋯π and π–π interactions [inter-centroid distances = 3.6443 (9) and 3.8557 (11) Å].

Related literature

For further synthetic details and the anti-convulsant activity of the title compound, see: El-Azab et al. (2011 ▶).

Experimental

Crystal data

C₂₃H₁₇ClN₂O₃
M _r = 404.84
Monoclinic,
a = 18.6703 (5) Å
b = 7.6203 (2) Å
c = 13.3756 (3) Å
β = 98.006 (3)°
V = 1884.44 (8) Å³
Z = 4
Cu Kα radiation
μ = 2.03 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.15 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T _min = 0.631, T _max = 0.750
7495 measured reflections
3883 independent reflections
3529 reflections with I > 2σ(I)
R _int = 0.020

Refinement

R[F ² > 2σ(F ²)] = 0.040
wR(F ²) = 0.108
S = 1.04
3883 reflections
287 parameters
16 restraints
H-atom parameters constrained
Δρ_max = 0.38 e Å⁻³
Δρ_min = −0.42 e Å⁻³

Data collection: CrysAlis PRO (Agilent, 2012 ▶); 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/S1600536812025147/hb6831sup1.cif

e-68-o2052-sup1.cif^{(24.2KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812025147/hb6831Isup2.hkl

e-68-o2052-Isup2.hkl^{(190.3KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812025147/hb6831Isup3.cml

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

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

Cg1 and Cg2 are the centroids of the N1,N2,C9–C11,C16 and C1–C6 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8A⋯Cl1ⁱ	0.98	2.82	3.6162 (17)	139
C8—H8C⋯O2ⁱⁱ	0.98	2.51	3.4058 (19)	153
C22—H22⋯N2ⁱⁱⁱ	0.95	2.55	3.457 (2)	159
C3—H3⋯Cg1ⁱⁱ	0.95	2.94	3.834 (2)	158
C12—H12⋯Cg2^iv	0.95	2.81	3.6865 (17)	154

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

Acknowledgments

The authors extend their appreciation to the Research Center of Pharmacy, King Saud University, for funding this work. They also thank the Ministry of Higher Education (Malaysia) for funding structural studies through the High-Impact Research scheme (UM.C/HIR/MOHE/SC/12).

supplementary crystallographic information

Comment

The title compound was previously investigated by us in relation to its biological activity (El-Azab et al., 2011) and we now describe its crystal structure.

The quinazolinyl fused-ring system in (I), Fig. 1, inclusive of the carbonyl-O1 and methyl-C8 atoms, is planar (r.m.s. deviation = 0.044 Å) with maximum deviations of 0.064 (2) Å [C12] and -0.065 (2) Å [C15]. The 2-tolyl ring is orthogonal to this plane, forming a dihedral angle of 89.51 (8)°. The ester group is also twisted significantly out of the plane with the C17—O3—C15—C14 torsion angle being -103.69 (16)°. The carboxylate group is co-planar with the attached benzene ring as seen in the value of the O2—C17—C18—C19 torsion angle of -4.7 (2)°.

Supramolecular layers are formed in the bc plane by a combination of C—H···Cl, C—H···O, C—H···N and C—H···π interactions, Table 1, as well as π—π interactions between centrosymmetrically related chlorobenzene rings [inter-centroid distance = 3.6443 (9) Å for symmetry operation: 1 - x, 2 - y, 1 - z]. Links between the layers along the a axis are of the type π—π and occur between the major component of the 2-tolyl rings [inter-centroid distance = 3.8557 (11) Å for symmetry operation: -x, -y, 1 - z], Fig. 2.

Experimental

The compound was prepared in accord with the literature procedure (El-Azab et al., 2011). A mixture of 8-hydroxymethaqualone (532 mg, 0.002 M) and 4-chlorobenzoyl chloride (365 mg, 0.0021 M) in 10 ml pyridine was stirred at room temperature for 10 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 solution as colourless prisms. M.pt: 493–495 K. Yield: 95%. ¹H NMR (CDCl₃): δ = 8.27–8.08 (m, 3H), 7.61 (d, 1H, J = 7.5 Hz), 7.55–7.37 (m, 6H), 7.15 (d, 1H, J = 7.5 Hz), 2.14 (s, 3H), 2.11 (s, 3H) p.p.m.. ¹³C NMR (CDCl₃): δ = 17.4, 24.3, 122.5, 125.1, 126.4, 127.1, 127.7, 129.0, 129.4, 131.6, 131.8, 135.4, 136.7, 140.2, 141.4, 146.0, 154.9, 161.1, 164.4 p.p.m.. MS (70 eV): m/z = 404, 406 (M +2).