2-Methyl-3-(2-methyl-phen-yl)-7-nitro-quinazolin-4(3H)-one.

In the title methaqua-lone analogue, C(16)H(13)N(3)O(3), the 2-tolyl group is almost orthogonal [dihedral angle = 85.20 (5)°] to the fused ring system (r.m.s. deviation of fitted non-H atoms = 0.029 Å). In the crystal, twofold symmetry generates two-mol-ecule aggregates linked by C-H⋯O and π-π inter-actions [ring centroid-centroid distance = 3.4967 (6) Å].

Related literature

For recent studies on synthesis, drug discovery and crystal structures of quinazoline-4(3H)-one derivatives, see: El-Azab et al. (2010 ▶, 2012 ▶). For the anti-convulsant activity of the title methaqua­lone analogue, see: El-Azab et al. (2011 ▶). For a related structure, see: Stephenson et al. (2011 ▶).

Experimental

Crystal data

C16H13N3O3

M = 295.29

Monoclinic,

a = 14.4614 (5) Å

b = 16.5383 (4) Å

c = 12.9968 (4) Å

β = 119.072 (4)°

V = 2716.78 (14) Å3

Z = 8

Cu Kα radiation

μ = 0.85 mm−1

T = 100 K

0.25 × 0.25 × 0.25 mm

Data collection

Agilent SuperNova Dual diffractometer with an Atlas detector

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.967, T max = 0.998

5450 measured reflections

2783 independent reflections

2570 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.099

S = 1.02

2783 reflections

201 parameters

H-atom parameters constrained

Δρmax = 0.24 e Å−3

Δρmin = −0.24 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/S1600536812007350/hb6642sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812007350/hb6642Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812007350/hb6642Isup3.cml

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

C16H13N3O3	F(000) = 1232
Mr = 295.29	Dx = 1.444 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 3546 reflections
a = 14.4614 (5) Å	θ = 3.9–76.4°
b = 16.5383 (4) Å	µ = 0.85 mm−1
c = 12.9968 (4) Å	T = 100 K
β = 119.072 (4)°	Cube, colourless
V = 2716.78 (14) Å3	0.25 × 0.25 × 0.25 mm
Z = 8

Agilent SuperNova Dual diffractometer with an Atlas detector	2783 independent reflections
Radiation source: SuperNova (Cu) X-ray Source	2570 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.013
Detector resolution: 10.4041 pixels mm-1	θmax = 76.6°, θmin = 4.4°
ω scan	h = −18→17
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −20→18
Tmin = 0.967, Tmax = 0.998	l = −10→16
5450 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0566P)2 + 1.6285P] where P = (Fo2 + 2Fc2)/3
2783 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.24 e Å−3
0 restraints	Δρmin = −0.24 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	0.59490 (6)	0.19268 (5)	0.43782 (7)	0.0250 (2)
O2	0.65765 (7)	0.61062 (5)	0.45232 (9)	0.0338 (2)
O3	0.48735 (7)	0.62439 (5)	0.36278 (8)	0.0330 (2)
N1	0.41702 (7)	0.21605 (6)	0.35394 (8)	0.0201 (2)
N2	0.34237 (7)	0.34733 (6)	0.30533 (8)	0.0217 (2)
N3	0.56777 (8)	0.58294 (6)	0.40625 (9)	0.0247 (2)
C1	0.44368 (9)	0.37812 (7)	0.35225 (9)	0.0196 (2)
C2	0.45504 (9)	0.46277 (7)	0.35369 (9)	0.0208 (2)
H2	0.3949	0.4972	0.3210	0.025*
C3	0.55556 (9)	0.49398 (7)	0.40369 (10)	0.0214 (2)
C4	0.64664 (9)	0.44647 (7)	0.45173 (10)	0.0225 (2)
H4	0.7148	0.4707	0.4859	0.027*
C5	0.63564 (9)	0.36354 (7)	0.44855 (9)	0.0215 (2)
H5	0.6964	0.3298	0.4795	0.026*
C6	0.53454 (9)	0.32924 (7)	0.39953 (9)	0.0195 (2)
C7	0.52197 (8)	0.24124 (7)	0.39980 (9)	0.0200 (2)
C8	0.33210 (8)	0.26981 (7)	0.30874 (9)	0.0211 (2)
C9	0.22363 (9)	0.23499 (7)	0.26233 (11)	0.0273 (3)
H9A	0.1715	0.2788	0.2356	0.041*
H9B	0.2199	0.2044	0.3248	0.041*
H9C	0.2084	0.1989	0.1962	0.041*
C10	0.39793 (8)	0.13076 (7)	0.36267 (10)	0.0207 (2)
C11	0.37329 (9)	0.08065 (7)	0.26703 (10)	0.0236 (2)
H11	0.3732	0.1011	0.1987	0.028*
C12	0.34882 (9)	0.00019 (7)	0.27286 (11)	0.0252 (3)
H12	0.3291	−0.0345	0.2071	0.030*
C13	0.35326 (9)	−0.02949 (7)	0.37522 (11)	0.0242 (3)
H13	0.3371	−0.0846	0.3798	0.029*
C14	0.38125 (9)	0.02132 (7)	0.47070 (10)	0.0232 (2)
H14	0.3863	−0.0001	0.5411	0.028*
C15	0.40209 (8)	0.10313 (7)	0.46597 (10)	0.0214 (2)
C16	0.42659 (10)	0.15867 (8)	0.56764 (10)	0.0270 (3)
H16A	0.4905	0.1899	0.5866	0.040*
H16B	0.4381	0.1266	0.6363	0.040*
H16C	0.3671	0.1957	0.5463	0.040*

	U11	U22	U33	U12	U13	U23
O1	0.0190 (4)	0.0239 (4)	0.0292 (4)	0.0027 (3)	0.0094 (3)	0.0001 (3)
O2	0.0311 (5)	0.0281 (5)	0.0405 (5)	−0.0096 (4)	0.0161 (4)	−0.0045 (4)
O3	0.0324 (5)	0.0247 (4)	0.0405 (5)	0.0026 (4)	0.0166 (4)	0.0039 (4)
N1	0.0172 (5)	0.0203 (5)	0.0208 (5)	−0.0004 (3)	0.0077 (4)	0.0000 (3)
N2	0.0180 (4)	0.0233 (5)	0.0217 (5)	0.0007 (4)	0.0080 (4)	0.0022 (4)
N3	0.0284 (5)	0.0241 (5)	0.0238 (5)	−0.0033 (4)	0.0143 (4)	−0.0008 (4)
C1	0.0190 (5)	0.0242 (5)	0.0158 (5)	0.0000 (4)	0.0087 (4)	0.0003 (4)
C2	0.0213 (5)	0.0237 (6)	0.0182 (5)	0.0017 (4)	0.0101 (4)	0.0015 (4)
C3	0.0265 (6)	0.0218 (5)	0.0183 (5)	−0.0021 (4)	0.0126 (4)	−0.0007 (4)
C4	0.0195 (5)	0.0275 (6)	0.0194 (5)	−0.0046 (4)	0.0088 (4)	−0.0023 (4)
C5	0.0185 (5)	0.0262 (6)	0.0187 (5)	0.0003 (4)	0.0082 (4)	−0.0005 (4)
C6	0.0194 (5)	0.0230 (5)	0.0160 (5)	−0.0002 (4)	0.0087 (4)	−0.0005 (4)
C7	0.0170 (5)	0.0245 (6)	0.0173 (5)	0.0003 (4)	0.0075 (4)	−0.0010 (4)
C8	0.0171 (5)	0.0251 (5)	0.0188 (5)	0.0004 (4)	0.0069 (4)	0.0014 (4)
C9	0.0175 (5)	0.0265 (6)	0.0326 (6)	−0.0001 (4)	0.0080 (5)	0.0038 (5)
C10	0.0161 (5)	0.0208 (5)	0.0226 (5)	−0.0002 (4)	0.0073 (4)	0.0006 (4)
C11	0.0216 (5)	0.0262 (6)	0.0217 (5)	−0.0001 (4)	0.0094 (4)	0.0001 (4)
C12	0.0223 (6)	0.0252 (6)	0.0260 (6)	−0.0021 (4)	0.0101 (5)	−0.0049 (4)
C13	0.0182 (5)	0.0221 (5)	0.0291 (6)	−0.0014 (4)	0.0090 (5)	0.0007 (4)
C14	0.0164 (5)	0.0269 (6)	0.0240 (6)	−0.0010 (4)	0.0081 (4)	0.0030 (4)
C15	0.0145 (5)	0.0252 (6)	0.0219 (5)	−0.0002 (4)	0.0068 (4)	−0.0010 (4)
C16	0.0270 (6)	0.0301 (6)	0.0227 (6)	−0.0035 (5)	0.0112 (5)	−0.0025 (5)

O1—C7	1.2227 (14)	C8—C9	1.4955 (15)
O2—N3	1.2253 (13)	C9—H9A	0.9800
O3—N3	1.2261 (14)	C9—H9B	0.9800
N1—C8	1.3938 (14)	C9—H9C	0.9800
N1—C7	1.3976 (14)	C10—C11	1.3887 (16)
N1—C10	1.4522 (14)	C10—C15	1.3915 (16)
N2—C8	1.2939 (15)	C11—C12	1.3885 (16)
N2—C1	1.3818 (14)	C11—H11	0.9500
N3—C3	1.4803 (14)	C12—C13	1.3899 (17)
C1—C6	1.4046 (15)	C12—H12	0.9500
C1—C2	1.4086 (15)	C13—C14	1.3863 (17)
C2—C3	1.3724 (16)	C13—H13	0.9500
C2—H2	0.9500	C14—C15	1.3939 (16)
C3—C4	1.3939 (16)	C14—H14	0.9500
C4—C5	1.3790 (16)	C15—C16	1.5035 (15)
C4—H4	0.9500	C16—H16A	0.9800
C5—C6	1.4000 (15)	C16—H16B	0.9800
C5—H5	0.9500	C16—H16C	0.9800
C6—C7	1.4670 (15)
C8—N1—C7	122.78 (9)	C8—C9—H9A	109.5
C8—N1—C10	119.37 (9)	C8—C9—H9B	109.5
C7—N1—C10	117.68 (9)	H9A—C9—H9B	109.5
C8—N2—C1	117.70 (9)	C8—C9—H9C	109.5
O2—N3—O3	124.04 (10)	H9A—C9—H9C	109.5
O2—N3—C3	117.96 (10)	H9B—C9—H9C	109.5
O3—N3—C3	117.99 (10)	C11—C10—C15	122.65 (11)
N2—C1—C6	123.15 (10)	C11—C10—N1	119.05 (10)
N2—C1—C2	117.64 (10)	C15—C10—N1	118.27 (10)
C6—C1—C2	119.20 (10)	C12—C11—C10	118.98 (11)
C3—C2—C1	118.02 (10)	C12—C11—H11	120.5
C3—C2—H2	121.0	C10—C11—H11	120.5
C1—C2—H2	121.0	C11—C12—C13	119.74 (11)
C2—C3—C4	123.58 (10)	C11—C12—H12	120.1
C2—C3—N3	118.14 (10)	C13—C12—H12	120.1
C4—C3—N3	118.28 (10)	C14—C13—C12	120.02 (11)
C5—C4—C3	118.49 (10)	C14—C13—H13	120.0
C5—C4—H4	120.8	C12—C13—H13	120.0
C3—C4—H4	120.8	C13—C14—C15	121.61 (11)
C4—C5—C6	119.76 (10)	C13—C14—H14	119.2
C4—C5—H5	120.1	C15—C14—H14	119.2
C6—C5—H5	120.1	C10—C15—C14	116.90 (10)
C5—C6—C1	120.93 (10)	C10—C15—C16	121.90 (10)
C5—C6—C7	120.27 (10)	C14—C15—C16	121.19 (10)
C1—C6—C7	118.77 (10)	C15—C16—H16A	109.5
O1—C7—N1	121.42 (10)	C15—C16—H16B	109.5
O1—C7—C6	124.68 (10)	H16A—C16—H16B	109.5
N1—C7—C6	113.88 (9)	C15—C16—H16C	109.5
N2—C8—N1	123.66 (10)	H16A—C16—H16C	109.5
N2—C8—C9	118.89 (10)	H16B—C16—H16C	109.5
N1—C8—C9	117.45 (10)
C8—N2—C1—C6	2.02 (16)	C1—C6—C7—O1	179.56 (10)
C8—N2—C1—C2	−176.98 (10)	C5—C6—C7—N1	176.62 (9)
N2—C1—C2—C3	177.87 (10)	C1—C6—C7—N1	−1.68 (14)
C6—C1—C2—C3	−1.17 (15)	C1—N2—C8—N1	−1.83 (16)
C1—C2—C3—C4	0.77 (17)	C1—N2—C8—C9	177.94 (10)
C1—C2—C3—N3	−179.48 (9)	C7—N1—C8—N2	−0.21 (17)
O2—N3—C3—C2	179.07 (10)	C10—N1—C8—N2	174.96 (10)
O3—N3—C3—C2	−0.50 (15)	C7—N1—C8—C9	−179.98 (10)
O2—N3—C3—C4	−1.17 (15)	C10—N1—C8—C9	−4.82 (15)
O3—N3—C3—C4	179.26 (10)	C8—N1—C10—C11	88.12 (13)
C2—C3—C4—C5	0.36 (17)	C7—N1—C10—C11	−96.47 (12)
N3—C3—C4—C5	−179.39 (9)	C8—N1—C10—C15	−90.00 (12)
C3—C4—C5—C6	−1.07 (16)	C7—N1—C10—C15	85.41 (13)
C4—C5—C6—C1	0.66 (16)	C15—C10—C11—C12	1.87 (17)
C4—C5—C6—C7	−177.60 (10)	N1—C10—C11—C12	−176.16 (10)
N2—C1—C6—C5	−178.50 (10)	C10—C11—C12—C13	−2.42 (17)
C2—C1—C6—C5	0.48 (16)	C11—C12—C13—C14	0.49 (17)
N2—C1—C6—C7	−0.22 (15)	C12—C13—C14—C15	2.14 (17)
C2—C1—C6—C7	178.77 (9)	C11—C10—C15—C14	0.65 (16)
C8—N1—C7—O1	−179.25 (10)	N1—C10—C15—C14	178.70 (9)
C10—N1—C7—O1	5.51 (15)	C11—C10—C15—C16	−178.64 (10)
C8—N1—C7—C6	1.94 (14)	N1—C10—C15—C16	−0.59 (16)
C10—N1—C7—C6	−173.30 (9)	C13—C14—C15—C10	−2.66 (16)
C5—C6—C7—O1	−2.15 (17)	C13—C14—C15—C16	176.63 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···O1i	0.95	2.54	3.4530 (15)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯O1i	0.95	2.54	3.4530 (15)	161

Symmetry code: (i) .