2-Methyl-3-(2-methyl-phen-yl)-4-oxo-3,4-dihydro-quinazolin-8-yl 4-methyl-benzoate.

In the title quinazolin-4-one derivative, C(24)H(20)N(2)O(3), both the 4-methyl-benzoate [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, mol-ecules 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] inter-actions.

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 = 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

Δρmax = 1.09 e Å−3

Δρmin = −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 ▶).

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

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

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

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

C24H20N2O3	F(000) = 808
Mr = 384.42	Dx = 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

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	Rint = 0.027
Detector resolution: 10.4041 pixels mm-1	θmax = 76.7°, θmin = 4.7°
ω scans	h = −23→23
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→9
Tmin = 0.755, Tmax = 1.000	l = −16→8
7966 measured reflections

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(Fo2) + (0.0962P)2 + 2.188P] where P = (Fo2 + 2Fc2)/3
3883 reflections	(Δ/σ)max < 0.001
265 parameters	Δρmax = 1.09 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .