2,3-Di-methyl-quinazolin-4(3H)-one.

The non-H atoms of the title mol-ecule, C10H10N2O, are essentially coplanar, with a maximum deviation of 0.046 (4) Å for the O atom. In the crystal, mol-ecules are linked by weak C-H⋯O hydrogen bonds, forming chains along [010]. In addtion, weak C-H⋯π inter-actions and π-π stacking inter-actions between benzene and pyrimidine rings, with a centroid-centroid distance of 3.730 (3) Å, link the chains, forming a two-dimensional network parallel to (001).

Related literature

For the synthesis of related compounds, see: Takeuchi & Eguchi (1989 ▶). For the crystal structure of a related compound, see: Makhloufi et al. (2013 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C10H10N2O

M = 174.20

Orthorhombic,

a = 4.826 (2) Å

b = 7.919 (3) Å

c = 23.060 (8) Å

V = 881.3 (11) Å3

Z = 4

Cu Kα radiation

μ = 0.71 mm−1

T = 293 K

0.40 × 0.10 × 0.08 mm

Data collection

Oxford Diffraction Xcalibur Ruby diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.041, T max = 1.000

2236 measured reflections

1585 independent reflections

821 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.071

wR(F 2) = 0.230

S = 0.97

1585 reflections

121 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.19 e Å−3

Absolute structure: Flack (1983 ▶), 507 Friedel pairs

Absolute structure parameter: −0.3 (12)

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, GLOBAL. DOI: 10.1107/S1600536814013749/lh5714sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814013749/lh5714Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814013749/lh5714Isup3.cml

CCDC reference: 1007927

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H10N2O	Dx = 1.313 Mg m−3
Mr = 174.20	Melting point: 491(2) K
Orthorhombic, P212121	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: P 2ac 2ab	Cell parameters from 333 reflections
a = 4.826 (2) Å	θ = 3.8–64.0°
b = 7.919 (3) Å	µ = 0.71 mm−1
c = 23.060 (8) Å	T = 293 K
V = 881.3 (11) Å3	Needle, colourless
Z = 4	0.40 × 0.10 × 0.08 mm
F(000) = 368

Oxford Diffraction Xcalibur Ruby diffractometer	1585 independent reflections
Radiation source: fine-focus sealed tube	821 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
Detector resolution: 10.2576 pixels mm-1	θmax = 75.9°, θmin = 3.8°
ω scans	h = −5→5
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −5→9
Tmin = 0.041, Tmax = 1.000	l = −28→28
2236 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.071	H-atom parameters constrained
wR(F2) = 0.230	w = 1/[σ2(Fo2) + (0.1116P)2] where P = (Fo2 + 2Fc2)/3
S = 0.97	(Δ/σ)max < 0.001
1585 reflections	Δρmax = 0.20 e Å−3
121 parameters	Δρmin = −0.19 e Å−3
0 restraints	Absolute structure: Flack (1983), 507 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.3 (12)

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
N3	0.3333 (9)	−0.1245 (5)	0.17512 (17)	0.0819 (12)
O1	0.4020 (9)	0.1511 (4)	0.19869 (17)	0.1055 (13)
N1	0.5799 (9)	−0.2643 (5)	0.10074 (17)	0.0846 (11)
C4A	0.6580 (10)	0.0357 (6)	0.1199 (2)	0.0773 (13)
C4	0.4620 (11)	0.0295 (7)	0.1667 (2)	0.0807 (13)
C10	0.1309 (12)	−0.1350 (7)	0.2233 (2)	0.1009 (17)
H10A	0.2040	−0.2059	0.2534	0.151*
H10B	−0.0397	−0.1819	0.2093	0.151*
H10C	0.0975	−0.0240	0.2386	0.151*
C8	0.8983 (11)	−0.1088 (7)	0.0431 (2)	0.0912 (15)
H8	0.9313	−0.2067	0.0219	0.109*
C2	0.4000 (11)	−0.2650 (6)	0.1422 (2)	0.0816 (13)
C8A	0.7099 (9)	−0.1120 (6)	0.0883 (2)	0.0769 (12)
C7	1.0368 (13)	0.0367 (8)	0.0292 (2)	0.1023 (16)
H7	1.1647	0.0374	−0.0010	0.123*
C9	0.2541 (14)	−0.4274 (7)	0.1551 (3)	0.109 (2)
H9A	0.2779	−0.4552	0.1954	0.164*
H9B	0.3305	−0.5158	0.1316	0.164*
H9C	0.0603	−0.4153	0.1468	0.164*
C6	0.9842 (12)	0.1838 (7)	0.0607 (3)	0.1019 (18)
H6	1.0776	0.2828	0.0514	0.122*
C5	0.7965 (12)	0.1837 (6)	0.1051 (2)	0.0923 (16)
H5	0.7615	0.2828	0.1255	0.111*

	U11	U22	U33	U12	U13	U23
N3	0.077 (2)	0.080 (3)	0.089 (3)	0.004 (2)	0.003 (2)	0.002 (2)
O1	0.118 (3)	0.083 (2)	0.115 (3)	0.008 (2)	−0.002 (3)	−0.024 (2)
N1	0.080 (2)	0.080 (2)	0.094 (3)	−0.004 (2)	0.002 (2)	−0.005 (2)
C4A	0.074 (3)	0.072 (3)	0.086 (3)	−0.001 (2)	−0.011 (3)	−0.001 (3)
C4	0.083 (3)	0.073 (3)	0.086 (3)	0.010 (3)	−0.011 (3)	−0.004 (3)
C10	0.100 (4)	0.104 (4)	0.098 (3)	0.020 (4)	0.012 (3)	0.008 (3)
C8	0.085 (3)	0.090 (3)	0.099 (3)	0.004 (3)	0.003 (3)	−0.012 (3)
C2	0.076 (3)	0.066 (3)	0.102 (3)	0.004 (3)	−0.006 (3)	−0.002 (3)
C8A	0.068 (3)	0.071 (3)	0.091 (3)	−0.001 (3)	−0.005 (3)	0.003 (3)
C7	0.092 (4)	0.117 (4)	0.098 (3)	−0.003 (4)	0.006 (3)	0.006 (4)
C9	0.103 (4)	0.077 (3)	0.147 (5)	−0.002 (3)	0.014 (4)	0.002 (4)
C6	0.096 (4)	0.092 (4)	0.118 (4)	−0.013 (3)	−0.008 (4)	0.022 (3)
C5	0.093 (4)	0.076 (3)	0.108 (4)	0.003 (3)	−0.009 (3)	−0.002 (3)

N3—C4	1.382 (6)	C8—C7	1.370 (7)
N3—C2	1.385 (6)	C8—C8A	1.383 (7)
N3—C10	1.482 (6)	C8—H8	0.9300
O1—C4	1.248 (6)	C2—C9	1.496 (7)
N1—C2	1.292 (6)	C7—C6	1.397 (8)
N1—C8A	1.390 (6)	C7—H7	0.9300
C4A—C5	1.392 (7)	C9—H9A	0.9600
C4A—C8A	1.400 (6)	C9—H9B	0.9600
C4A—C4	1.436 (7)	C9—H9C	0.9600
C10—H10A	0.9600	C6—C5	1.368 (7)
C10—H10B	0.9600	C6—H6	0.9300
C10—H10C	0.9600	C5—H5	0.9300
C4—N3—C2	121.8 (4)	N1—C2—C9	117.9 (5)
C4—N3—C10	116.8 (4)	N3—C2—C9	118.2 (5)
C2—N3—C10	121.3 (5)	C8—C8A—N1	117.9 (5)
C2—N1—C8A	117.4 (4)	C8—C8A—C4A	119.6 (5)
C5—C4A—C8A	119.4 (5)	N1—C8A—C4A	122.4 (4)
C5—C4A—C4	121.9 (5)	C8—C7—C6	119.4 (5)
C8A—C4A—C4	118.7 (5)	C8—C7—H7	120.3
O1—C4—N3	119.5 (5)	C6—C7—H7	120.3
O1—C4—C4A	124.9 (5)	C2—C9—H9A	109.5
N3—C4—C4A	115.6 (4)	C2—C9—H9B	109.5
N3—C10—H10A	109.5	H9A—C9—H9B	109.5
N3—C10—H10B	109.5	C2—C9—H9C	109.5
H10A—C10—H10B	109.5	H9A—C9—H9C	109.5
N3—C10—H10C	109.5	H9B—C9—H9C	109.5
H10A—C10—H10C	109.5	C5—C6—C7	120.7 (5)
H10B—C10—H10C	109.5	C5—C6—H6	119.7
C7—C8—C8A	120.8 (5)	C7—C6—H6	119.7
C7—C8—H8	119.6	C6—C5—C4A	120.1 (5)
C8A—C8—H8	119.6	C6—C5—H5	120.0
N1—C2—N3	124.0 (5)	C4A—C5—H5	120.0

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10A···O1i	0.96	2.47	3.345 (8)	151
C10—H10B···Cgii	0.96	2.80	3.608 (6)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the N1/C2/N3/C4/C4A/C8A ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10A⋯O1i	0.96	2.47	3.345 (8)	151
C10—H10B⋯Cg ii	0.96	2.80	3.608 (6)	142

Symmetry codes: (i) ; (ii) .