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

In the title quinazolin-4-one derivative, C(23)H(18)N(2)O(3), both the benzoate [dihedral angle = 79.99 (6)°] and the 2-tolyl [89.02 (7)°] groups are close to orthogonal to the central fused ring system. Both aryl groups are orientated 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⋯N and C-H⋯π inter-actions.

Related literature

For the pharmacological activity of substituted quinazoline-4(3H)-ones, see: El-Azab & El-Tahir (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 anti-convulsant 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

C23H18N2O3

M = 370.39

Monoclinic,

a = 20.3847 (4) Å

b = 7.4352 (1) Å

c = 12.7829 (3) Å

β = 107.489 (2)°

V = 1847.87 (6) Å3

Z = 4

Cu Kα radiation

μ = 0.72 mm−1

T = 100 K

0.30 × 0.10 × 0.05 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.470, T max = 1.000

7377 measured reflections

3780 independent reflections

3432 reflections with I > 2σ(I)

R int = 0.015

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.132

S = 1.05

3780 reflections

255 parameters

H-atom parameters constrained

Δρmax = 0.61 e Å−3

Δρmin = −0.28 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/S1600536812006253/hb6635sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812006253/hb6635Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812006253/hb6635Isup3.cml

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

C23H18N2O3	F(000) = 776
Mr = 370.39	Dx = 1.331 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 4141 reflections
a = 20.3847 (4) Å	θ = 3.6–76.0°
b = 7.4352 (1) Å	µ = 0.72 mm−1
c = 12.7829 (3) Å	T = 100 K
β = 107.489 (2)°	Prism, colourless
V = 1847.87 (6) Å3	0.30 × 0.10 × 0.05 mm
Z = 4

Agilent SuperNova Dual diffractometer with an Atlas detector	3780 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	3432 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.015
Detector resolution: 10.4041 pixels mm-1	θmax = 76.1°, θmin = 4.6°
ω scan	h = −22→25
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −9→6
Tmin = 0.470, Tmax = 1.000	l = −15→15
7377 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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0621P)2 + 1.4481P] where P = (Fo2 + 2Fc2)/3
3780 reflections	(Δ/σ)max = 0.001
255 parameters	Δρmax = 0.61 e Å−3
0 restraints	Δρmin = −0.28 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	0.12153 (6)	0.28357 (15)	0.64163 (9)	0.0228 (3)
O2	0.17292 (6)	0.08881 (17)	0.55602 (10)	0.0287 (3)
O3	0.39006 (6)	0.65559 (18)	0.84640 (10)	0.0284 (3)
N1	0.21618 (7)	0.52042 (18)	0.60240 (11)	0.0197 (3)
N2	0.31826 (7)	0.69110 (19)	0.67202 (11)	0.0209 (3)
C1	0.05574 (8)	0.1737 (2)	0.46895 (13)	0.0220 (3)
C2	−0.00084 (9)	0.2669 (2)	0.48010 (14)	0.0248 (4)
H2	0.0028	0.3330	0.5452	0.030*
C3	−0.06272 (9)	0.2636 (2)	0.39634 (16)	0.0295 (4)
H3	−0.1014	0.3278	0.4038	0.035*
C4	−0.06782 (10)	0.1661 (2)	0.30169 (16)	0.0313 (4)
H4	−0.1101	0.1640	0.2443	0.038*
C5	−0.01162 (10)	0.0715 (2)	0.29002 (15)	0.0301 (4)
H5	−0.0156	0.0047	0.2251	0.036*
C6	0.05038 (9)	0.0750 (2)	0.37355 (14)	0.0258 (4)
H6	0.0890	0.0107	0.3660	0.031*
C7	0.12288 (8)	0.1733 (2)	0.55681 (13)	0.0212 (3)
C8	0.18435 (8)	0.3093 (2)	0.72251 (13)	0.0212 (3)
C9	0.19716 (9)	0.2213 (2)	0.82114 (14)	0.0248 (4)
H9	0.1646	0.1378	0.8323	0.030*
C10	0.25825 (9)	0.2546 (2)	0.90526 (14)	0.0254 (4)
H10	0.2674	0.1922	0.9730	0.030*
C11	0.30502 (9)	0.3773 (2)	0.89015 (13)	0.0225 (3)
H11	0.3466	0.3995	0.9470	0.027*
C12	0.29094 (8)	0.4695 (2)	0.79007 (13)	0.0195 (3)
C13	0.23106 (8)	0.4352 (2)	0.70379 (12)	0.0187 (3)
C14	0.33798 (8)	0.6088 (2)	0.77586 (13)	0.0205 (3)
C15	0.25920 (8)	0.6410 (2)	0.59004 (12)	0.0192 (3)
C16	0.24555 (9)	0.7342 (2)	0.48214 (13)	0.0238 (3)
H16A	0.2042	0.6836	0.4300	0.036*
H16B	0.2849	0.7174	0.4540	0.036*
H16C	0.2387	0.8629	0.4916	0.036*
C17	0.36264 (9)	0.8369 (2)	0.65716 (13)	0.0250 (4)
C18	0.35070 (9)	1.0096 (2)	0.69125 (15)	0.0276 (4)
H18	0.3126	1.0318	0.7177	0.033*
C19	0.39532 (9)	1.1478 (2)	0.68583 (15)	0.0303 (4)
H19	0.3875	1.2663	0.7071	0.036*
C20	0.45170 (9)	1.1116 (3)	0.64898 (14)	0.0290 (4)
H20	0.4829	1.2055	0.6469	0.035*
C21	0.46277 (9)	0.9408 (2)	0.61541 (14)	0.0269 (4)
H21	0.5012	0.9189	0.5898	0.032*
C22	0.41779 (9)	0.7985 (2)	0.61865 (13)	0.0250 (4)
C23	0.43021 (10)	0.6146 (2)	0.58317 (15)	0.0297 (4)
H23A	0.4362	0.5307	0.6444	0.045*
H23B	0.4718	0.6148	0.5599	0.045*
H23C	0.3908	0.5770	0.5218	0.045*

	U11	U22	U33	U12	U13	U23
O1	0.0196 (5)	0.0213 (6)	0.0261 (6)	−0.0029 (4)	0.0049 (5)	−0.0053 (4)
O2	0.0236 (6)	0.0286 (6)	0.0320 (6)	0.0019 (5)	0.0052 (5)	−0.0065 (5)
O3	0.0232 (6)	0.0370 (7)	0.0205 (6)	−0.0089 (5)	−0.0003 (5)	0.0019 (5)
N1	0.0201 (6)	0.0176 (6)	0.0194 (6)	0.0010 (5)	0.0031 (5)	−0.0019 (5)
N2	0.0207 (7)	0.0233 (7)	0.0172 (6)	−0.0032 (5)	0.0034 (5)	0.0002 (5)
C1	0.0230 (8)	0.0166 (7)	0.0250 (8)	−0.0042 (6)	0.0053 (6)	0.0010 (6)
C2	0.0256 (8)	0.0181 (7)	0.0299 (9)	−0.0026 (6)	0.0070 (7)	−0.0002 (6)
C3	0.0249 (9)	0.0220 (8)	0.0385 (10)	0.0004 (7)	0.0049 (7)	0.0034 (7)
C4	0.0288 (9)	0.0246 (8)	0.0322 (9)	−0.0049 (7)	−0.0033 (7)	0.0055 (7)
C5	0.0370 (10)	0.0244 (8)	0.0249 (8)	−0.0061 (7)	0.0031 (7)	−0.0011 (7)
C6	0.0278 (8)	0.0218 (8)	0.0274 (8)	−0.0024 (7)	0.0075 (7)	−0.0015 (6)
C7	0.0239 (8)	0.0154 (7)	0.0251 (8)	−0.0030 (6)	0.0083 (7)	−0.0013 (6)
C8	0.0207 (8)	0.0183 (7)	0.0234 (8)	−0.0002 (6)	0.0046 (6)	−0.0042 (6)
C9	0.0287 (9)	0.0187 (8)	0.0285 (8)	−0.0036 (6)	0.0110 (7)	−0.0005 (6)
C10	0.0334 (9)	0.0211 (8)	0.0218 (8)	0.0001 (7)	0.0084 (7)	0.0016 (6)
C11	0.0254 (8)	0.0219 (8)	0.0186 (7)	0.0004 (6)	0.0043 (6)	−0.0005 (6)
C12	0.0212 (7)	0.0180 (7)	0.0190 (7)	0.0007 (6)	0.0058 (6)	−0.0019 (6)
C13	0.0213 (7)	0.0164 (7)	0.0186 (7)	0.0018 (6)	0.0060 (6)	−0.0021 (6)
C14	0.0199 (7)	0.0230 (8)	0.0177 (7)	0.0004 (6)	0.0043 (6)	−0.0011 (6)
C15	0.0194 (7)	0.0188 (7)	0.0182 (7)	0.0018 (6)	0.0036 (6)	−0.0025 (6)
C16	0.0253 (8)	0.0233 (8)	0.0192 (7)	−0.0009 (6)	0.0012 (6)	0.0012 (6)
C17	0.0241 (8)	0.0292 (9)	0.0190 (7)	−0.0042 (7)	0.0023 (6)	0.0024 (6)
C18	0.0259 (8)	0.0253 (8)	0.0301 (9)	−0.0018 (7)	0.0062 (7)	−0.0002 (7)
C19	0.0323 (9)	0.0246 (9)	0.0317 (9)	−0.0009 (7)	0.0061 (7)	−0.0031 (7)
C20	0.0259 (8)	0.0296 (9)	0.0276 (8)	−0.0036 (7)	0.0018 (7)	0.0009 (7)
C21	0.0258 (8)	0.0282 (9)	0.0227 (8)	−0.0013 (7)	0.0013 (6)	0.0062 (7)
C22	0.0261 (8)	0.0251 (8)	0.0207 (8)	0.0007 (7)	0.0027 (6)	0.0022 (6)
C23	0.0333 (9)	0.0270 (9)	0.0286 (9)	−0.0011 (7)	0.0090 (7)	0.0018 (7)

O1—C7	1.3661 (19)	C10—C11	1.375 (2)
O1—C8	1.3962 (19)	C10—H10	0.9500
O2—C7	1.201 (2)	C11—C12	1.403 (2)
O3—C14	1.219 (2)	C11—H11	0.9500
N1—C15	1.296 (2)	C12—C13	1.401 (2)
N1—C13	1.392 (2)	C12—C14	1.459 (2)
N2—C15	1.3887 (19)	C15—C16	1.493 (2)
N2—C14	1.406 (2)	C16—H16A	0.9800
N2—C17	1.461 (2)	C16—H16B	0.9800
C1—C2	1.389 (2)	C16—H16C	0.9800
C1—C6	1.399 (2)	C17—C22	1.386 (3)
C1—C7	1.487 (2)	C17—C18	1.400 (3)
C2—C3	1.388 (2)	C18—C19	1.387 (3)
C2—H2	0.9500	C18—H18	0.9500
C3—C4	1.387 (3)	C19—C20	1.393 (3)
C3—H3	0.9500	C19—H19	0.9500
C4—C5	1.390 (3)	C20—C21	1.381 (3)
C4—H4	0.9500	C20—H20	0.9500
C5—C6	1.388 (2)	C21—C22	1.409 (2)
C5—H5	0.9500	C21—H21	0.9500
C6—H6	0.9500	C22—C23	1.486 (2)
C8—C9	1.374 (2)	C23—H23A	0.9800
C8—C13	1.406 (2)	C23—H23B	0.9800
C9—C10	1.401 (2)	C23—H23C	0.9800
C9—H9	0.9500
C7—O1—C8	115.93 (12)	C11—C12—C14	119.88 (14)
C15—N1—C13	117.52 (13)	N1—C13—C12	123.02 (14)
C15—N2—C14	122.18 (14)	N1—C13—C8	119.49 (14)
C15—N2—C17	122.11 (13)	C12—C13—C8	117.48 (14)
C14—N2—C17	115.68 (13)	O3—C14—N2	120.83 (15)
C2—C1—C6	120.09 (15)	O3—C14—C12	124.70 (15)
C2—C1—C7	121.84 (15)	N2—C14—C12	114.47 (13)
C6—C1—C7	118.07 (15)	N1—C15—N2	123.95 (14)
C3—C2—C1	120.16 (16)	N1—C15—C16	119.25 (14)
C3—C2—H2	119.9	N2—C15—C16	116.80 (14)
C1—C2—H2	119.9	C15—C16—H16A	109.5
C4—C3—C2	119.63 (17)	C15—C16—H16B	109.5
C4—C3—H3	120.2	H16A—C16—H16B	109.5
C2—C3—H3	120.2	C15—C16—H16C	109.5
C3—C4—C5	120.66 (16)	H16A—C16—H16C	109.5
C3—C4—H4	119.7	H16B—C16—H16C	109.5
C5—C4—H4	119.7	C22—C17—C18	122.36 (16)
C6—C5—C4	119.82 (17)	C22—C17—N2	119.55 (16)
C6—C5—H5	120.1	C18—C17—N2	117.88 (15)
C4—C5—H5	120.1	C19—C18—C17	119.04 (17)
C5—C6—C1	119.65 (17)	C19—C18—H18	120.5
C5—C6—H6	120.2	C17—C18—H18	120.5
C1—C6—H6	120.2	C18—C19—C20	119.58 (17)
O2—C7—O1	122.72 (15)	C18—C19—H19	120.2
O2—C7—C1	125.87 (15)	C20—C19—H19	120.2
O1—C7—C1	111.41 (13)	C21—C20—C19	120.75 (17)
C9—C8—O1	119.55 (15)	C21—C20—H20	119.6
C9—C8—C13	121.44 (15)	C19—C20—H20	119.6
O1—C8—C13	118.85 (14)	C20—C21—C22	120.87 (17)
C8—C9—C10	119.99 (15)	C20—C21—H21	119.6
C8—C9—H9	120.0	C22—C21—H21	119.6
C10—C9—H9	120.0	C17—C22—C21	117.38 (16)
C11—C10—C9	120.24 (15)	C17—C22—C23	121.95 (16)
C11—C10—H10	119.9	C21—C22—C23	120.66 (16)
C9—C10—H10	119.9	C22—C23—H23A	109.5
C10—C11—C12	119.46 (15)	C22—C23—H23B	109.5
C10—C11—H11	120.3	H23A—C23—H23B	109.5
C12—C11—H11	120.3	C22—C23—H23C	109.5
C13—C12—C11	121.35 (15)	H23A—C23—H23C	109.5
C13—C12—C14	118.73 (14)	H23B—C23—H23C	109.5
C6—C1—C2—C3	−0.5 (2)	O1—C8—C13—C12	174.56 (13)
C7—C1—C2—C3	−179.84 (15)	C15—N2—C14—O3	−179.91 (15)
C1—C2—C3—C4	0.3 (3)	C17—N2—C14—O3	−1.9 (2)
C2—C3—C4—C5	0.1 (3)	C15—N2—C14—C12	−0.8 (2)
C3—C4—C5—C6	−0.3 (3)	C17—N2—C14—C12	177.21 (14)
C4—C5—C6—C1	0.1 (3)	C13—C12—C14—O3	176.86 (16)
C2—C1—C6—C5	0.3 (3)	C11—C12—C14—O3	−1.0 (3)
C7—C1—C6—C5	179.68 (15)	C13—C12—C14—N2	−2.2 (2)
C8—O1—C7—O2	7.2 (2)	C11—C12—C14—N2	179.96 (14)
C8—O1—C7—C1	−172.79 (13)	C13—N1—C15—N2	−0.9 (2)
C2—C1—C7—O2	175.74 (16)	C13—N1—C15—C16	179.36 (14)
C6—C1—C7—O2	−3.6 (3)	C14—N2—C15—N1	2.5 (2)
C2—C1—C7—O1	−4.3 (2)	C17—N2—C15—N1	−175.36 (15)
C6—C1—C7—O1	176.36 (14)	C14—N2—C15—C16	−177.75 (14)
C7—O1—C8—C9	−103.54 (17)	C17—N2—C15—C16	4.4 (2)
C7—O1—C8—C13	81.03 (17)	C15—N2—C17—C22	−92.04 (19)
O1—C8—C9—C10	−176.08 (14)	C14—N2—C17—C22	89.96 (18)
C13—C8—C9—C10	−0.8 (3)	C15—N2—C17—C18	93.06 (19)
C8—C9—C10—C11	1.0 (3)	C14—N2—C17—C18	−84.94 (19)
C9—C10—C11—C12	0.3 (3)	C22—C17—C18—C19	0.4 (3)
C10—C11—C12—C13	−1.9 (2)	N2—C17—C18—C19	175.12 (15)
C10—C11—C12—C14	175.82 (15)	C17—C18—C19—C20	−1.4 (3)
C15—N1—C13—C12	−2.4 (2)	C18—C19—C20—C21	1.5 (3)
C15—N1—C13—C8	177.21 (14)	C19—C20—C21—C22	−0.7 (3)
C11—C12—C13—N1	−178.26 (14)	C18—C17—C22—C21	0.5 (2)
C14—C12—C13—N1	4.0 (2)	N2—C17—C22—C21	−174.21 (14)
C11—C12—C13—C8	2.1 (2)	C18—C17—C22—C23	179.70 (16)
C14—C12—C13—C8	−175.64 (14)	N2—C17—C22—C23	5.0 (2)
C9—C8—C13—N1	179.61 (15)	C20—C21—C22—C17	−0.3 (2)
O1—C8—C13—N1	−5.0 (2)	C20—C21—C22—C23	−179.57 (16)
C9—C8—C13—C12	−0.8 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···N1i	0.95	2.58	3.521 (2)	172
C16—H16c···O2ii	0.98	2.44	3.298 (2)	146
C20—H20···O3iii	0.95	2.59	3.225 (2)	124
C11—H11···Cg1iv	0.95	2.72	3.5519 (18)	147

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C17–C22 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯N1i	0.95	2.58	3.521 (2)	172
C16—H16c⋯O2ii	0.98	2.44	3.298 (2)	146
C20—H20⋯O3iii	0.95	2.59	3.225 (2)	124
C11—H11⋯Cg1iv	0.95	2.72	3.5519 (18)	147

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