2-{[2-Methyl-3-(2-methyl-phen-yl)-4-oxo-3,4-dihydro-quinazolin-8-yl]-oxy}acetonitrile.

In the title compound, C(18)H(15)N(3)O(2), the fused ring system is almost planar [the dihedral angle between the six-membered rings is 1.81 (6)°]. The 2-tolyl ring is approximately orthogonal to this plane [dihedral angle = 83.03 (7)°] as is the acetonitrile group [C-O-C-C torsion angle = 79.24 (14)°] which is also syn to the methyl substituent of the tolyl group. In the crystal, supra-molecular layers are formed in the bc plane mediated by C-H⋯O, C-H⋯N and C-H⋯π inter-actions. The tolyl group is disordered over two positions in a 0.852 (3):0.148 (3) ratio.

Related literature

For the biological activity of quinazoline-4(3H)-one derivatives, see: El-Azab et al. (2010 ▶, 2011 ▶); El-Azab & ElTahir (2012 ▶). For a related structure, see: Abdel-Aziz et al. (2012 ▶).

Experimental

Crystal data

C18H15N3O2

M = 305.33

Monoclinic,

a = 15.4721 (3) Å

b = 6.7775 (1) Å

c = 15.0124 (4) Å

β = 109.143 (3)°

V = 1487.18 (5) Å3

Z = 4

Cu Kα radiation

μ = 0.74 mm−1

T = 100 K

0.30 × 0.25 × 0.20 mm

Data collection

Agilent SuperNova Dual diffractometer with Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012 ▶) T min = 0.808, T max = 0.866

10100 measured reflections

3088 independent reflections

2908 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.123

S = 1.09

3088 reflections

233 parameters

58 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.20 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 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812026165/xu5559sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812026165/xu5559Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812026165/xu5559Isup3.cml

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

C18H15N3O2	F(000) = 640
Mr = 305.33	Dx = 1.364 Mg m−3
Monoclinic, P21/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2ybc	Cell parameters from 5616 reflections
a = 15.4721 (3) Å	θ = 3.0–76.1°
b = 6.7775 (1) Å	µ = 0.74 mm−1
c = 15.0124 (4) Å	T = 100 K
β = 109.143 (3)°	Prism, colourless
V = 1487.18 (5) Å3	0.30 × 0.25 × 0.20 mm
Z = 4

Agilent SuperNova Dual diffractometer with Atlas detector	3088 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2908 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.018
Detector resolution: 10.4041 pixels mm-1	θmax = 76.3°, θmin = 3.0°
ω scan	h = −13→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012)	k = −8→8
Tmin = 0.808, Tmax = 0.866	l = −18→18
10100 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.6598P] where P = (Fo2 + 2Fc2)/3
3088 reflections	(Δ/σ)max = 0.001
233 parameters	Δρmax = 0.27 e Å−3
58 restraints	Δρmin = −0.20 e Å−3

	x	y	z	Uiso*/Ueq	Occ. (<1)
O1	0.85217 (7)	0.62011 (15)	0.76440 (7)	0.0273 (2)
O2	0.54879 (6)	0.18507 (14)	0.48673 (6)	0.0219 (2)
N1	0.67419 (7)	0.16913 (16)	0.65621 (7)	0.0191 (2)
N2	0.79168 (8)	0.31930 (17)	0.78022 (8)	0.0240 (3)
N3	0.56836 (9)	0.0563 (2)	0.27639 (9)	0.0335 (3)
C1	0.84789 (10)	0.3118 (2)	0.88003 (10)	0.0198 (3)	0.852 (3)
C2	0.80993 (12)	0.3639 (3)	0.94860 (12)	0.0236 (4)	0.852 (3)
H2	0.7479	0.4052	0.9309	0.028*	0.852 (3)
C3	0.86293 (11)	0.3554 (3)	1.04297 (11)	0.0254 (4)	0.852 (3)
H3	0.8372	0.3884	1.0905	0.031*	0.852 (3)
C4	0.95376 (11)	0.2982 (2)	1.06740 (12)	0.0251 (4)	0.852 (3)
H4	0.9908	0.2941	1.1319	0.030*	0.852 (3)
C5	0.99064 (13)	0.2473 (3)	0.99821 (12)	0.0238 (4)	0.852 (3)
H5	1.0529	0.2079	1.0161	0.029*	0.852 (3)
C6	0.93854 (10)	0.2525 (2)	0.90252 (11)	0.0209 (3)	0.852 (3)
C7	0.97864 (12)	0.1972 (3)	0.82743 (12)	0.0266 (4)	0.852 (3)
H7A	0.9439	0.0872	0.7902	0.040*	0.852 (3)
H7B	1.0426	0.1576	0.8570	0.040*	0.852 (3)
H7C	0.9756	0.3108	0.7861	0.040*	0.852 (3)
C1'	0.8823 (5)	0.2844 (13)	0.8555 (5)	0.0198 (3)	0.148
C2'	0.9622 (6)	0.2131 (19)	0.8473 (7)	0.0236 (4)	0.148
H2'	0.9647	0.1831	0.7864	0.028*	0.148 (3)
C3'	1.0393 (6)	0.1834 (14)	0.9251 (5)	0.0254 (4)	0.148
H3'	1.0942	0.1315	0.9191	0.031*	0.148 (3)
C4'	1.0329 (7)	0.2322 (16)	1.0114 (6)	0.0251 (4)	0.148
H4'	1.0851	0.2179	1.0661	0.030*	0.148 (3)
C5'	0.9526 (5)	0.3015 (15)	1.0207 (7)	0.0238 (4)	0.148
H5'	0.9500	0.3279	1.0819	0.029*	0.148 (3)
C6'	0.8746 (5)	0.3340 (13)	0.9418 (5)	0.0209 (3)	0.148
C7'	0.7884 (7)	0.4203 (19)	0.9493 (9)	0.0266 (4)	0.148
H7'1	0.7802	0.5539	0.9229	0.040*	0.148 (3)
H7'2	0.7922	0.4255	1.0157	0.040*	0.148 (3)
H7'3	0.7363	0.3380	0.9141	0.040*	0.148 (3)
C8	0.73758 (10)	−0.0128 (2)	0.80091 (10)	0.0269 (3)
H8A	0.6914	−0.1089	0.7665	0.040*
H8B	0.7263	0.0254	0.8591	0.040*
H8C	0.7986	−0.0718	0.8166	0.040*
C9	0.73225 (9)	0.16577 (19)	0.74080 (9)	0.0207 (3)
C10	0.79631 (9)	0.49066 (19)	0.72958 (9)	0.0214 (3)
C11	0.72916 (8)	0.49846 (19)	0.63470 (9)	0.0194 (3)
C12	0.72363 (9)	0.6660 (2)	0.57818 (10)	0.0233 (3)
H12	0.7641	0.7740	0.6006	0.028*
C13	0.65887 (10)	0.6718 (2)	0.48982 (10)	0.0250 (3)
H13	0.6546	0.7848	0.4512	0.030*
C14	0.59904 (9)	0.5124 (2)	0.45607 (9)	0.0226 (3)
H14	0.5547	0.5182	0.3949	0.027*
C15	0.60444 (9)	0.34748 (19)	0.51141 (9)	0.0194 (3)
C16	0.67042 (8)	0.33768 (19)	0.60284 (9)	0.0180 (3)
C17	0.48506 (9)	0.1754 (2)	0.39353 (9)	0.0214 (3)
H17A	0.4566	0.3065	0.3750	0.026*
H17B	0.4360	0.0802	0.3916	0.026*
C18	0.53176 (9)	0.1132 (2)	0.32659 (9)	0.0241 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0235 (5)	0.0235 (5)	0.0290 (5)	−0.0051 (4)	0.0005 (4)	−0.0022 (4)
O2	0.0232 (5)	0.0227 (5)	0.0156 (4)	−0.0063 (4)	0.0008 (4)	0.0008 (3)
N1	0.0191 (5)	0.0192 (5)	0.0179 (5)	−0.0005 (4)	0.0045 (4)	−0.0012 (4)
N2	0.0230 (6)	0.0212 (6)	0.0209 (6)	−0.0026 (4)	−0.0022 (4)	−0.0004 (4)
N3	0.0336 (7)	0.0396 (7)	0.0273 (6)	−0.0035 (6)	0.0100 (5)	−0.0055 (5)
C1	0.0192 (8)	0.0207 (7)	0.0170 (8)	−0.0021 (6)	0.0028 (6)	−0.0016 (6)
C2	0.0183 (8)	0.0276 (9)	0.0244 (8)	−0.0003 (6)	0.0061 (7)	−0.0028 (7)
C3	0.0281 (8)	0.0283 (8)	0.0214 (7)	−0.0048 (6)	0.0100 (6)	−0.0036 (6)
C4	0.0271 (8)	0.0258 (8)	0.0190 (8)	−0.0061 (6)	0.0029 (6)	−0.0004 (6)
C5	0.0174 (8)	0.0254 (8)	0.0267 (8)	−0.0020 (7)	0.0046 (7)	0.0022 (6)
C6	0.0207 (7)	0.0205 (7)	0.0212 (7)	−0.0016 (6)	0.0064 (6)	−0.0004 (6)
C7	0.0246 (9)	0.0314 (9)	0.0254 (9)	0.0048 (7)	0.0105 (6)	0.0007 (7)
C1'	0.0192 (8)	0.0207 (7)	0.0170 (8)	−0.0021 (6)	0.0028 (6)	−0.0016 (6)
C2'	0.0183 (8)	0.0276 (9)	0.0244 (8)	−0.0003 (6)	0.0061 (7)	−0.0028 (7)
C3'	0.0281 (8)	0.0283 (8)	0.0214 (7)	−0.0048 (6)	0.0100 (6)	−0.0036 (6)
C4'	0.0271 (8)	0.0258 (8)	0.0190 (8)	−0.0061 (6)	0.0029 (6)	−0.0004 (6)
C5'	0.0174 (8)	0.0254 (8)	0.0267 (8)	−0.0020 (7)	0.0046 (7)	0.0022 (6)
C6'	0.0207 (7)	0.0205 (7)	0.0212 (7)	−0.0016 (6)	0.0064 (6)	−0.0004 (6)
C7'	0.0246 (9)	0.0314 (9)	0.0254 (9)	0.0048 (7)	0.0105 (6)	0.0007 (7)
C8	0.0319 (7)	0.0218 (7)	0.0210 (6)	−0.0029 (5)	0.0006 (5)	0.0016 (5)
C9	0.0201 (6)	0.0200 (6)	0.0200 (6)	−0.0005 (5)	0.0039 (5)	−0.0022 (5)
C10	0.0184 (6)	0.0206 (6)	0.0235 (6)	−0.0002 (5)	0.0045 (5)	−0.0023 (5)
C11	0.0176 (6)	0.0208 (6)	0.0195 (6)	−0.0001 (5)	0.0058 (5)	−0.0018 (5)
C12	0.0229 (6)	0.0214 (6)	0.0254 (7)	−0.0038 (5)	0.0077 (5)	−0.0014 (5)
C13	0.0294 (7)	0.0222 (6)	0.0235 (7)	−0.0021 (5)	0.0088 (5)	0.0038 (5)
C14	0.0233 (6)	0.0252 (7)	0.0182 (6)	−0.0013 (5)	0.0051 (5)	0.0007 (5)
C15	0.0191 (6)	0.0208 (6)	0.0185 (6)	−0.0026 (5)	0.0063 (5)	−0.0026 (5)
C16	0.0170 (6)	0.0197 (6)	0.0180 (6)	0.0003 (5)	0.0066 (5)	−0.0011 (5)
C17	0.0193 (6)	0.0264 (7)	0.0156 (6)	−0.0037 (5)	0.0017 (5)	0.0001 (5)
C18	0.0231 (6)	0.0268 (7)	0.0187 (6)	−0.0042 (5)	0.0019 (5)	0.0000 (5)

O1—C10	1.2222 (17)	C3'—C4'	1.372 (8)
O2—C15	1.3714 (15)	C3'—H3'	0.9500
O2—C17	1.4246 (14)	C4'—C5'	1.376 (8)
N1—C9	1.2930 (16)	C4'—H4'	0.9500
N1—C16	1.3854 (17)	C5'—C6'	1.404 (8)
N2—C9	1.3862 (17)	C5'—H5'	0.9500
N2—C10	1.4027 (18)	C6'—C7'	1.492 (8)
N2—C1	1.4661 (17)	C7'—H7'1	0.9800
N2—C1'	1.504 (7)	C7'—H7'2	0.9800
N3—C18	1.148 (2)	C7'—H7'3	0.9800
C1—C2	1.388 (2)	C8—C9	1.4956 (18)
C1—C6	1.390 (2)	C8—H8A	0.9800
C2—C3	1.386 (2)	C8—H8B	0.9800
C2—H2	0.9500	C8—H8C	0.9800
C3—C4	1.386 (2)	C10—C11	1.4631 (17)
C3—H3	0.9500	C11—C16	1.3990 (18)
C4—C5	1.383 (2)	C11—C12	1.4030 (19)
C4—H4	0.9500	C12—C13	1.3760 (19)
C5—C6	1.398 (2)	C12—H12	0.9500
C5—H5	0.9500	C13—C14	1.4045 (19)
C6—C7	1.501 (2)	C13—H13	0.9500
C7—H7A	0.9800	C14—C15	1.3788 (19)
C7—H7B	0.9800	C14—H14	0.9500
C7—H7C	0.9800	C15—C16	1.4183 (17)
C1'—C2'	1.369 (8)	C17—C18	1.4785 (19)
C1'—C6'	1.382 (7)	C17—H17A	0.9900
C2'—C3'	1.383 (8)	C17—H17B	0.9900
C2'—H2'	0.9500
C15—O2—C17	118.25 (10)	C6'—C7'—H7'1	109.5
C9—N1—C16	117.80 (11)	C6'—C7'—H7'2	109.5
C9—N2—C10	122.33 (11)	H7'1—C7'—H7'2	109.5
C9—N2—C1	119.90 (11)	C6'—C7'—H7'3	109.5
C10—N2—C1	117.64 (11)	H7'1—C7'—H7'3	109.5
C9—N2—C1'	121.8 (4)	H7'2—C7'—H7'3	109.5
C10—N2—C1'	109.7 (4)	C9—C8—H8A	109.5
C2—C1—C6	122.15 (14)	C9—C8—H8B	109.5
C2—C1—N2	119.73 (13)	H8A—C8—H8B	109.5
C6—C1—N2	118.11 (13)	C9—C8—H8C	109.5
C3—C2—C1	119.69 (15)	H8A—C8—H8C	109.5
C3—C2—H2	120.2	H8B—C8—H8C	109.5
C1—C2—H2	120.2	N1—C9—N2	123.78 (12)
C2—C3—C4	119.39 (15)	N1—C9—C8	119.34 (12)
C2—C3—H3	120.3	N2—C9—C8	116.88 (11)
C4—C3—H3	120.3	O1—C10—N2	121.15 (12)
C5—C4—C3	120.21 (16)	O1—C10—C11	124.56 (12)
C5—C4—H4	119.9	N2—C10—C11	114.29 (11)
C3—C4—H4	119.9	C16—C11—C12	121.31 (12)
C4—C5—C6	121.65 (17)	C16—C11—C10	118.62 (12)
C4—C5—H5	119.2	C12—C11—C10	120.07 (12)
C6—C5—H5	119.2	C13—C12—C11	119.14 (12)
C1—C6—C5	116.90 (14)	C13—C12—H12	120.4
C1—C6—C7	121.48 (14)	C11—C12—H12	120.4
C5—C6—C7	121.62 (14)	C12—C13—C14	120.74 (12)
C2'—C1'—C6'	121.9 (7)	C12—C13—H13	119.6
C2'—C1'—N2	129.4 (6)	C14—C13—H13	119.6
C6'—C1'—N2	108.6 (5)	C15—C14—C13	120.24 (12)
C1'—C2'—C3'	122.0 (8)	C15—C14—H14	119.9
C1'—C2'—H2'	119.0	C13—C14—H14	119.9
C3'—C2'—H2'	119.0	O2—C15—C14	125.40 (11)
C4'—C3'—C2'	116.9 (8)	O2—C15—C16	114.38 (11)
C4'—C3'—H3'	121.6	C14—C15—C16	120.21 (12)
C2'—C3'—H3'	121.6	N1—C16—C11	123.03 (12)
C5'—C4'—C3'	121.7 (8)	N1—C16—C15	118.60 (11)
C5'—C4'—H4'	119.2	C11—C16—C15	118.36 (12)
C3'—C4'—H4'	119.2	O2—C17—C18	110.21 (10)
C4'—C5'—C6'	121.6 (8)	O2—C17—H17A	109.6
C4'—C5'—H5'	119.2	C18—C17—H17A	109.6
C6'—C5'—H5'	119.2	O2—C17—H17B	109.6
C1'—C6'—C5'	115.9 (7)	C18—C17—H17B	109.6
C1'—C6'—C7'	121.3 (7)	H17A—C17—H17B	108.1
C5'—C6'—C7'	122.8 (8)	N3—C18—C17	176.83 (16)
C9—N2—C1—C2	−80.62 (18)	C10—N2—C9—N1	−2.5 (2)
C10—N2—C1—C2	95.27 (17)	C1—N2—C9—N1	173.15 (13)
C1'—N2—C1—C2	176.6 (7)	C1'—N2—C9—N1	−152.1 (3)
C9—N2—C1—C6	99.54 (17)	C10—N2—C9—C8	176.97 (12)
C10—N2—C1—C6	−84.56 (17)	C1—N2—C9—C8	−7.33 (19)
C1'—N2—C1—C6	−3.2 (7)	C1'—N2—C9—C8	27.4 (4)
C6—C1—C2—C3	−0.6 (3)	C9—N2—C10—O1	−176.60 (13)
N2—C1—C2—C3	179.53 (14)	C1—N2—C10—O1	7.61 (19)
C1—C2—C3—C4	1.1 (3)	C1'—N2—C10—O1	−23.8 (3)
C2—C3—C4—C5	−1.0 (3)	C9—N2—C10—C11	3.95 (18)
C3—C4—C5—C6	0.3 (3)	C1—N2—C10—C11	−171.84 (11)
C2—C1—C6—C5	0.0 (2)	C1'—N2—C10—C11	156.7 (3)
N2—C1—C6—C5	179.79 (13)	O1—C10—C11—C16	178.61 (13)
C2—C1—C6—C7	−179.81 (16)	N2—C10—C11—C16	−1.97 (17)
N2—C1—C6—C7	0.0 (2)	O1—C10—C11—C12	−2.4 (2)
C4—C5—C6—C1	0.2 (2)	N2—C10—C11—C12	177.05 (12)
C4—C5—C6—C7	179.99 (16)	C16—C11—C12—C13	0.2 (2)
C9—N2—C1'—C2'	77.1 (11)	C10—C11—C12—C13	−178.82 (12)
C10—N2—C1'—C2'	−75.8 (11)	C11—C12—C13—C14	−0.2 (2)
C1—N2—C1'—C2'	172.7 (16)	C12—C13—C14—C15	0.1 (2)
C9—N2—C1'—C6'	−101.8 (6)	C17—O2—C15—C14	5.87 (18)
C10—N2—C1'—C6'	105.3 (6)	C17—O2—C15—C16	−175.36 (10)
C1—N2—C1'—C6'	−6.3 (4)	C13—C14—C15—O2	178.74 (12)
C6'—C1'—C2'—C3'	1.2 (18)	C13—C14—C15—C16	0.0 (2)
N2—C1'—C2'—C3'	−177.6 (9)	C9—N1—C16—C11	3.16 (18)
C1'—C2'—C3'—C4'	−1.2 (17)	C9—N1—C16—C15	−177.30 (11)
C2'—C3'—C4'—C5'	2.1 (16)	C12—C11—C16—N1	179.49 (12)
C3'—C4'—C5'—C6'	−2.9 (16)	C10—C11—C16—N1	−1.50 (18)
C2'—C1'—C6'—C5'	−1.8 (14)	C12—C11—C16—C15	−0.06 (19)
N2—C1'—C6'—C5'	177.2 (7)	C10—C11—C16—C15	178.95 (11)
C2'—C1'—C6'—C7'	177.2 (11)	O2—C15—C16—N1	1.55 (17)
N2—C1'—C6'—C7'	−3.8 (12)	C14—C15—C16—N1	−179.61 (12)
C4'—C5'—C6'—C1'	2.7 (14)	O2—C15—C16—C11	−178.89 (11)
C4'—C5'—C6'—C7'	−176.3 (10)	C14—C15—C16—C11	−0.05 (18)
C16—N1—C9—N2	−1.16 (19)	C15—O2—C17—C18	79.24 (14)
C16—N1—C9—C8	179.33 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1i	0.95	2.49	3.275 (2)	140
C8—H8C···O1ii	0.98	2.47	3.2048 (18)	132
C17—H17B···O2iii	0.99	2.52	3.1768 (16)	124
C17—H17B···N1iii	0.99	2.34	3.2976 (18)	163
C3—H3···Cg1iv	0.95	2.95	3.6775 (18)	134
C17—H17A···Cg2v	0.99	2.83	3.4979 (15)	125

Table 1

Hydrogen-bond geometry (Å, °)

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

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O1i	0.95	2.49	3.275 (2)	140
C8—H8C⋯O1ii	0.98	2.47	3.2048 (18)	132
C17—H17B⋯O2iii	0.99	2.52	3.1768 (16)	124
C17—H17B⋯N1iii	0.99	2.34	3.2976 (18)	163
C3—H3⋯Cg1iv	0.95	2.95	3.6775 (18)	134
C17—H17A⋯Cg2v	0.99	2.83	3.4979 (15)	125

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