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

El-Azab, A.S.; Abdel-Aziz, A.A.-M.; Ng, S.W.; Tiekink, E.R.T.

doi:10.1107/S1600536812006265

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o734-o735

doi:10.1107/S1600536812006265

Open

access

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 and Edward R. T. Tiekink ^d ^*

^aDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, ^bDepartment of Organic Chemistry, Faculty of Pharmacy, Al-Azhar University, Cairo 11884, Egypt, ^cDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt, ^dDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia, and ^eChemistry Department, Faculty of Science, King Abdulaziz University, PO Box 80203 Jeddah, Saudi Arabia
^*Correspondence e-mail: edward.tiekink@gmail.com

(Received 12 February 2012; accepted 12 February 2012; online 17 February 2012)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.067
wR(F²) = 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

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
Symmetry codes: (i) x, y-1, z; (ii) -x, -y, -z+1; (iii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812006265/hb6636sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536812006265/hb6636Isup3.cml

checkCIF report

Comment top

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.

Related literature top

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 top

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.

Computing details top

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, 2006); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 2. A view in projection down the c axis of the unit-cell contents for (I). The C—H···O, C—H···π and π–π interactions are shown as orange, brown and purple dashed lines, respectively.

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

Crystal data top

C₂₄H₂₀N₂O₃	F(000) = 808
M_r = 384.42	D_x = 1.346 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 3857 reflections
a = 18.8216 (5) Å	θ = 3.4–76.5°
b = 7.6332 (2) Å	µ = 0.72 mm⁻¹
c = 13.3092 (3) Å	T = 100 K
β = 97.286 (2)°	Prism, colourless
V = 1896.68 (8) Å³	0.25 × 0.20 × 0.15 mm
Z = 4

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3883 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3478 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.027
Detector resolution: 10.4041 pixels mm^-1	θ_max = 76.7°, θ_min = 4.7°
ω scans	h = −23→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→9
T_min = 0.755, T_max = 1.000	l = −16→8
7966 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.186	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0962P)² + 2.188P] where P = (F_o² + 2F_c²)/3
3883 reflections	(Δ/σ)_max < 0.001
265 parameters	Δρ_max = 1.09 e Å⁻³
0 restraints	Δρ_min = −0.33 e Å⁻³

Crystal data top

C₂₄H₂₀N₂O₃	V = 1896.68 (8) Å³
M_r = 384.42	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 18.8216 (5) Å	µ = 0.72 mm⁻¹
b = 7.6332 (2) Å	T = 100 K
c = 13.3092 (3) Å	0.25 × 0.20 × 0.15 mm
β = 97.286 (2)°

Data collection top

Agilent SuperNova Dual diffractometer with an Atlas detector	3883 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	3478 reflections with I > 2σ(I)
T_min = 0.755, T_max = 1.000	R_int = 0.027
7966 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.067	0 restraints
wR(F²) = 0.186	H-atom parameters constrained
S = 1.06	Δρ_max = 1.09 e Å⁻³
3883 reflections	Δρ_min = −0.33 e Å⁻³
265 parameters

Special details top

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 F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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) top

	x	y	z	U_iso*/U_eq
O1	0.37531 (7)	0.7195 (2)	0.60223 (11)	0.0223 (3)
O2	0.31966 (8)	0.9210 (2)	0.49638 (12)	0.0279 (4)
O3	0.10542 (9)	0.3305 (2)	0.65096 (12)	0.0339 (4)
N1	0.27420 (9)	0.4903 (2)	0.50849 (12)	0.0211 (4)
N2	0.17341 (10)	0.3084 (3)	0.52035 (13)	0.0267 (4)
C1	0.43599 (11)	0.8207 (3)	0.46864 (15)	0.0212 (4)
C2	0.49532 (11)	0.7190 (3)	0.50441 (16)	0.0238 (4)
H2	0.4958	0.6552	0.5658	0.029*
C3	0.55359 (11)	0.7105 (3)	0.45073 (16)	0.0246 (4)
H3	0.5939	0.6414	0.4760	0.030*
C4	0.55385 (11)	0.8024 (3)	0.35973 (16)	0.0237 (4)
C5	0.49471 (12)	0.9054 (3)	0.32543 (16)	0.0254 (5)
H5	0.4943	0.9695	0.2642	0.030*
C6	0.43625 (11)	0.9158 (3)	0.37932 (16)	0.0235 (4)
H6	0.3965	0.9877	0.3553	0.028*
C7	0.61739 (12)	0.7901 (3)	0.30194 (17)	0.0277 (5)
H7A	0.6324	0.6674	0.2988	0.041*
H7B	0.6569	0.8599	0.3363	0.041*
H7C	0.6042	0.8348	0.2331	0.041*
C8	0.37095 (11)	0.8299 (3)	0.52067 (15)	0.0209 (4)
C9	0.31180 (11)	0.6918 (3)	0.64461 (15)	0.0210 (4)
C10	0.30198 (11)	0.7733 (3)	0.73413 (15)	0.0233 (4)
H10	0.3360	0.8566	0.7634	0.028*
C11	0.24158 (12)	0.7332 (3)	0.78214 (15)	0.0255 (5)
H11	0.2340	0.7921	0.8428	0.031*
C12	0.19361 (11)	0.6093 (3)	0.74151 (15)	0.0236 (4)
H12	0.1533	0.5808	0.7746	0.028*
C13	0.20422 (11)	0.5243 (3)	0.65079 (15)	0.0214 (4)
C14	0.26278 (10)	0.5673 (3)	0.59976 (14)	0.0195 (4)
C15	0.15613 (11)	0.3839 (3)	0.61094 (15)	0.0252 (5)
C16	0.23027 (11)	0.3681 (3)	0.47275 (15)	0.0228 (4)
C17	0.24100 (12)	0.2818 (3)	0.37470 (16)	0.0270 (5)
H17A	0.2801	0.3402	0.3458	0.040*
H17B	0.1968	0.2906	0.3273	0.040*
H17C	0.2531	0.1581	0.3869	0.040*
C18	0.12952 (13)	0.1602 (3)	0.47919 (16)	0.0311 (5)
C19	0.15047 (12)	−0.0095 (3)	0.50999 (18)	0.0316 (5)
H19	0.1922	−0.0288	0.5567	0.038*
C20	0.10838 (14)	−0.1495 (3)	0.47021 (19)	0.0348 (5)
H20	0.1219	−0.2665	0.4880	0.042*
C21	0.04685 (13)	−0.1168 (4)	0.40471 (19)	0.0362 (6)
H21	0.0177	−0.2127	0.3794	0.043*
C22	0.02648 (14)	0.0491 (4)	0.37508 (18)	0.0350 (6)
H22	−0.0158	0.0669	0.3291	0.042*
C23	0.06853 (13)	0.1950 (4)	0.41299 (18)	0.0333 (5)
C24	0.04695 (14)	0.3739 (4)	0.3848 (2)	0.0406 (6)
H24A	0.0457	0.4443	0.4461	0.061*
H24B	−0.0008	0.3725	0.3455	0.061*
H24C	0.0814	0.4250	0.3437	0.061*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0183 (7)	0.0267 (8)	0.0224 (7)	−0.0018 (6)	0.0046 (5)	0.0041 (6)
O2	0.0240 (7)	0.0329 (9)	0.0279 (8)	0.0037 (6)	0.0072 (6)	0.0059 (6)
O3	0.0299 (8)	0.0486 (11)	0.0258 (8)	−0.0159 (7)	0.0138 (6)	−0.0061 (7)
N1	0.0214 (8)	0.0249 (9)	0.0181 (8)	−0.0008 (7)	0.0062 (6)	0.0012 (7)
N2	0.0267 (9)	0.0356 (11)	0.0194 (8)	−0.0107 (8)	0.0094 (7)	−0.0046 (7)
C1	0.0214 (10)	0.0221 (10)	0.0205 (9)	−0.0031 (8)	0.0043 (7)	−0.0025 (8)
C2	0.0239 (10)	0.0247 (11)	0.0233 (10)	−0.0016 (8)	0.0044 (8)	0.0014 (8)
C3	0.0232 (10)	0.0225 (11)	0.0286 (11)	0.0005 (8)	0.0054 (8)	0.0004 (8)
C4	0.0246 (10)	0.0235 (10)	0.0243 (10)	−0.0048 (8)	0.0083 (8)	−0.0056 (8)
C5	0.0290 (11)	0.0271 (11)	0.0209 (10)	−0.0024 (9)	0.0065 (8)	0.0012 (8)
C6	0.0230 (10)	0.0247 (10)	0.0227 (10)	−0.0004 (8)	0.0032 (8)	0.0008 (8)
C7	0.0283 (11)	0.0281 (11)	0.0286 (11)	−0.0006 (9)	0.0113 (9)	−0.0020 (9)
C8	0.0212 (9)	0.0223 (10)	0.0193 (9)	−0.0029 (8)	0.0030 (7)	−0.0009 (7)
C9	0.0189 (9)	0.0239 (10)	0.0209 (9)	0.0005 (8)	0.0057 (7)	0.0044 (8)
C10	0.0269 (10)	0.0209 (10)	0.0218 (10)	−0.0011 (8)	0.0015 (8)	0.0013 (8)
C11	0.0321 (11)	0.0273 (11)	0.0183 (9)	0.0010 (9)	0.0080 (8)	−0.0001 (8)
C12	0.0238 (10)	0.0286 (11)	0.0195 (9)	0.0006 (8)	0.0075 (8)	0.0018 (8)
C13	0.0205 (9)	0.0266 (10)	0.0178 (9)	−0.0003 (8)	0.0054 (7)	0.0024 (8)
C14	0.0201 (9)	0.0231 (10)	0.0159 (9)	0.0013 (8)	0.0040 (7)	0.0022 (7)
C15	0.0237 (10)	0.0344 (12)	0.0188 (9)	−0.0042 (9)	0.0074 (8)	−0.0003 (8)
C16	0.0241 (10)	0.0273 (11)	0.0183 (9)	−0.0028 (8)	0.0078 (8)	0.0016 (8)
C17	0.0309 (11)	0.0317 (12)	0.0203 (10)	−0.0060 (9)	0.0108 (8)	−0.0036 (8)
C18	0.0319 (12)	0.0415 (14)	0.0218 (10)	−0.0080 (10)	0.0102 (9)	−0.0064 (9)
C19	0.0276 (11)	0.0339 (13)	0.0347 (12)	−0.0023 (9)	0.0096 (9)	−0.0011 (10)
C20	0.0356 (12)	0.0355 (13)	0.0355 (12)	−0.0007 (10)	0.0131 (10)	0.0001 (10)
C21	0.0293 (12)	0.0482 (15)	0.0334 (12)	−0.0061 (11)	0.0128 (9)	−0.0019 (11)
C22	0.0357 (12)	0.0456 (14)	0.0254 (11)	0.0019 (11)	0.0106 (9)	−0.0053 (10)
C23	0.0307 (12)	0.0432 (14)	0.0276 (11)	−0.0010 (10)	0.0106 (9)	−0.0032 (10)
C24	0.0332 (13)	0.0548 (17)	0.0332 (13)	0.0001 (12)	0.0013 (10)	−0.0041 (12)

Geometric parameters (Å, º) top

O1—C8	1.368 (2)	C10—C11	1.407 (3)
O1—C9	1.401 (2)	C10—H10	0.9500
O2—C8	1.201 (3)	C11—C12	1.370 (3)
O3—C15	1.220 (3)	C11—H11	0.9500
N1—C16	1.296 (3)	C12—C13	1.407 (3)
N1—C14	1.390 (3)	C12—H12	0.9500
N2—C16	1.388 (3)	C13—C14	1.405 (3)
N2—C15	1.411 (3)	C13—C15	1.459 (3)
N2—C18	1.465 (3)	C16—C17	1.498 (3)
C1—C6	1.393 (3)	C17—H17A	0.9800
C1—C2	1.394 (3)	C17—H17B	0.9800
C1—C8	1.483 (3)	C17—H17C	0.9800
C2—C3	1.384 (3)	C18—C23	1.381 (3)
C2—H2	0.9500	C18—C19	1.400 (4)
C3—C4	1.400 (3)	C19—C20	1.394 (3)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.391 (3)	C20—C21	1.381 (4)
C4—C7	1.505 (3)	C20—H20	0.9500
C5—C6	1.390 (3)	C21—C22	1.367 (4)
C5—H5	0.9500	C21—H21	0.9500
C6—H6	0.9500	C22—C23	1.421 (4)
C7—H7A	0.9800	C22—H22	0.9500
C7—H7B	0.9800	C23—C24	1.460 (4)
C7—H7C	0.9800	C24—H24A	0.9800
C9—C10	1.377 (3)	C24—H24B	0.9800
C9—C14	1.404 (3)	C24—H24C	0.9800

C8—O1—C9	116.36 (15)	C13—C12—H12	120.0
C16—N1—C14	117.56 (17)	C14—C13—C12	120.85 (19)
C16—N2—C15	122.04 (18)	C14—C13—C15	118.97 (18)
C16—N2—C18	120.91 (17)	C12—C13—C15	120.12 (18)
C15—N2—C18	117.04 (17)	N1—C14—C9	119.44 (17)
C6—C1—C2	119.51 (19)	N1—C14—C13	122.78 (18)
C6—C1—C8	117.80 (19)	C9—C14—C13	117.77 (18)
C2—C1—C8	122.68 (19)	O3—C15—N2	121.0 (2)
C3—C2—C1	120.2 (2)	O3—C15—C13	124.76 (19)
C3—C2—H2	119.9	N2—C15—C13	114.28 (17)
C1—C2—H2	119.9	N1—C16—N2	124.17 (18)
C2—C3—C4	120.9 (2)	N1—C16—C17	119.07 (18)
C2—C3—H3	119.6	N2—C16—C17	116.75 (18)
C4—C3—H3	119.6	C16—C17—H17A	109.5
C5—C4—C3	118.45 (19)	C16—C17—H17B	109.5
C5—C4—C7	121.5 (2)	H17A—C17—H17B	109.5
C3—C4—C7	120.1 (2)	C16—C17—H17C	109.5
C6—C5—C4	121.1 (2)	H17A—C17—H17C	109.5
C6—C5—H5	119.5	H17B—C17—H17C	109.5
C4—C5—H5	119.5	C23—C18—C19	123.1 (2)
C5—C6—C1	119.9 (2)	C23—C18—N2	118.2 (2)
C5—C6—H6	120.0	C19—C18—N2	118.7 (2)
C1—C6—H6	120.0	C20—C19—C18	118.2 (2)
C4—C7—H7A	109.5	C20—C19—H19	120.9
C4—C7—H7B	109.5	C18—C19—H19	120.9
H7A—C7—H7B	109.5	C21—C20—C19	119.4 (2)
C4—C7—H7C	109.5	C21—C20—H20	120.3
H7A—C7—H7C	109.5	C19—C20—H20	120.3
H7B—C7—H7C	109.5	C22—C21—C20	122.1 (3)
O2—C8—O1	122.40 (18)	C22—C21—H21	118.9
O2—C8—C1	125.79 (19)	C20—C21—H21	118.9
O1—C8—C1	111.81 (17)	C21—C22—C23	120.0 (2)
C10—C9—O1	119.68 (18)	C21—C22—H22	120.0
C10—C9—C14	121.38 (18)	C23—C22—H22	120.0
O1—C9—C14	118.63 (18)	C18—C23—C22	117.1 (2)
C9—C10—C11	120.0 (2)	C18—C23—C24	121.7 (2)
C9—C10—H10	120.0	C22—C23—C24	121.2 (2)
C11—C10—H10	120.0	C23—C24—H24A	109.5
C12—C11—C10	120.06 (19)	C23—C24—H24B	109.5
C12—C11—H11	120.0	H24A—C24—H24B	109.5
C10—C11—H11	120.0	C23—C24—H24C	109.5
C11—C12—C13	119.92 (19)	H24A—C24—H24C	109.5
C11—C12—H12	120.0	H24B—C24—H24C	109.5

C6—C1—C2—C3	−1.0 (3)	C12—C13—C14—C9	2.7 (3)
C8—C1—C2—C3	177.69 (19)	C15—C13—C14—C9	−174.38 (18)
C1—C2—C3—C4	−0.4 (3)	C16—N2—C15—O3	179.2 (2)
C2—C3—C4—C5	1.2 (3)	C18—N2—C15—O3	−2.1 (3)
C2—C3—C4—C7	−179.4 (2)	C16—N2—C15—C13	−1.9 (3)
C3—C4—C5—C6	−0.7 (3)	C18—N2—C15—C13	176.80 (19)
C7—C4—C5—C6	180.0 (2)	C14—C13—C15—O3	176.9 (2)
C4—C5—C6—C1	−0.7 (3)	C12—C13—C15—O3	−0.3 (3)
C2—C1—C6—C5	1.5 (3)	C14—C13—C15—N2	−2.0 (3)
C8—C1—C6—C5	−177.18 (19)	C12—C13—C15—N2	−179.15 (19)
C9—O1—C8—O2	12.0 (3)	C14—N1—C16—N2	−0.8 (3)
C9—O1—C8—C1	−167.83 (17)	C14—N1—C16—C17	−179.84 (18)
C6—C1—C8—O2	−5.0 (3)	C15—N2—C16—N1	3.5 (3)
C2—C1—C8—O2	176.3 (2)	C18—N2—C16—N1	−175.1 (2)
C6—C1—C8—O1	174.84 (17)	C15—N2—C16—C17	−177.4 (2)
C2—C1—C8—O1	−3.8 (3)	C18—N2—C16—C17	4.0 (3)
C8—O1—C9—C10	−103.9 (2)	C16—N2—C18—C23	−92.2 (3)
C8—O1—C9—C14	82.5 (2)	C15—N2—C18—C23	89.1 (3)
O1—C9—C10—C11	−173.89 (18)	C16—N2—C18—C19	88.9 (3)
C14—C9—C10—C11	−0.4 (3)	C15—N2—C18—C19	−89.7 (3)
C9—C10—C11—C12	1.9 (3)	C23—C18—C19—C20	1.3 (3)
C10—C11—C12—C13	−1.1 (3)	N2—C18—C19—C20	−179.9 (2)
C11—C12—C13—C14	−1.3 (3)	C18—C19—C20—C21	−1.9 (3)
C11—C12—C13—C15	175.8 (2)	C19—C20—C21—C22	1.8 (4)
C16—N1—C14—C9	175.77 (19)	C20—C21—C22—C23	−0.9 (4)
C16—N1—C14—C13	−3.4 (3)	C19—C18—C23—C22	−0.5 (3)
C10—C9—C14—N1	178.96 (19)	N2—C18—C23—C22	−179.30 (19)
O1—C9—C14—N1	−7.5 (3)	C19—C18—C23—C24	178.1 (2)
C10—C9—C14—C13	−1.9 (3)	N2—C18—C23—C24	−0.7 (3)
O1—C9—C14—C13	171.66 (17)	C21—C22—C23—C18	0.3 (3)
C12—C13—C14—N1	−178.11 (18)	C21—C22—C23—C24	−178.3 (2)
C15—C13—C14—N1	4.8 (3)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z+1; (iii) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₂O₃
M_r	384.42
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	18.8216 (5), 7.6332 (2), 13.3092 (3)
β (°)	97.286 (2)
V (Å³)	1896.68 (8)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	0.72
Crystal size (mm)	0.25 × 0.20 × 0.15

Data collection
Diffractometer	Agilent SuperNova Dual diffractometer with an Atlas detector
Absorption correction	Multi-scan (CrysAlis PRO; Agilent, 2011)
T_min, T_max	0.755, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7966, 3883, 3478
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.631

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.067, 0.186, 1.06
No. of reflections	3883
No. of parameters	265
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.09, −0.33

Computer programs: CrysAlis PRO (Agilent, 2011), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z+1; (iii) x, −y+1/2, z+1/2.

Footnotes

‡Additional correspondence author, e-mail: adelazaba@yahoo.com.

Acknowledgements

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).

References

Agilent (2011). CrysAlis PRO. Agilent Technologies, Yarnton, Oxfordshire, England. Google Scholar
Al-Obaid, A. M., Abdel-Hamide, S. G., El-Kashef, H. A., Abdel-Aziz, A. A.-M., El-Azab, A. S., Al-Khamees, H. A. & El-Subbagh, H. I. (2009). Eur. J. Med. Chem. 44, 2379–2391. Web of Science PubMed CAS Google Scholar
Al-Omary, F. A., Abou-Zeid, L. A., Nagi, M. N., Habib, S. E., Abdel-Aziz, A. A.-M., Hamide, S. G., Al-Omar, M. A., Al-Obaid, A. M. & El-Subbagh, H. I. (2010). Bioorg. Med. Chem. 18, 2849–2863. Web of Science CAS PubMed Google Scholar
Aziza, M. A., Nassar, M. W. I., Abdel Hamid, S. G., El-Hakim, A. E. & El-Azab, A. S. (1996). Indian J. Heterocycl. Chem, 6, 25–30. CAS Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
El-Azab, A. S., Abdel-Aziz, A. A.-M., Ng, S. W. & Tiekink, E. R. T. (2012). Acta Cryst. E68, o732–o733. CSD CrossRef IUCr Journals Google Scholar
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, 4188–4198. Web of Science CAS PubMed Google Scholar
El-Azab, A. S. & ElTahir, K. H. (2012). Bioorg. Med. Chem. Lett. 22, 327–333. Web of Science CAS PubMed Google Scholar
El-Azab, A. S., ElTahir, K. H. & Attia, S. M. (2011). Monatsh. Chem. 142, 837–848. CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Pages o734-o735

doi:10.1107/S1600536812006265

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Footnotes

Acknowledgements

References

organic compounds

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