3,8-Dimethyl-quinazoline-2,4(1H,3H)-dione.

In the title compound, C(10)H(10)N(2)O(2), all non-H atoms are approximately co-planar with an r.m.s. deviation of 0.016 Å. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯O hydrogen bonds. Chains along [010] are buiilt up by π-π inter-actions [centroid-centroid distance = 3.602 (1) Å] between the benzene and piperazine rings of adjacent mol-ecules.

Related literature

For the synthesis and background to the title compound, see Feng et al. (2010 ▶).

Experimental

Crystal data

C10H10N2O2

M = 190.20

Monoclinic,

a = 8.3604 (17) Å

b = 4.8599 (10) Å

c = 22.288 (5) Å

β = 92.09 (3)°

V = 905.0 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 295 K

0.29 × 0.23 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.972, T max = 0.981

8373 measured reflections

2085 independent reflections

1497 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.043

wR(F 2) = 0.143

S = 1.10

2085 reflections

133 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.22 e Å−3

Δρmin = −0.18 e Å−3

Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002) ▶; 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: SHELXL97.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811025232/ng5192sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811025232/ng5192Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811025232/ng5192Isup3.cml

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

C10H10N2O2	F(000) = 400
Mr = 190.20	Dx = 1.396 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6086 reflections
a = 8.3604 (17) Å	θ = 3.0–27.5°
b = 4.8599 (10) Å	µ = 0.10 mm−1
c = 22.288 (5) Å	T = 295 K
β = 92.09 (3)°	Block, colorless
V = 905.0 (3) Å3	0.29 × 0.23 × 0.19 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	2085 independent reflections
Radiation source: fine-focus sealed tube	1497 reflections with I > 2σ(I)
graphite	Rint = 0.030
ω scan	θmax = 27.5°, θmin = 3.0°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −10→10
Tmin = 0.972, Tmax = 0.981	k = −6→6
8373 measured reflections	l = −28→28

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ2(Fo2) + (0.0833P)2 + 0.0221P] where P = (Fo2 + 2Fc2)/3
2085 reflections	(Δ/σ)max < 0.001
133 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.18 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.36317 (16)	0.6713 (2)	0.37609 (6)	0.0319 (3)
C2	0.47592 (17)	0.4802 (3)	0.35641 (6)	0.0378 (3)
C3	0.43348 (19)	0.3256 (3)	0.30632 (7)	0.0436 (4)
H3	0.5058	0.1965	0.2927	0.052*
C4	0.2866 (2)	0.3552 (3)	0.27525 (7)	0.0459 (4)
H4	0.2625	0.2481	0.2415	0.055*
C5	0.17879 (18)	0.5421 (3)	0.29463 (6)	0.0420 (4)
H5	0.0807	0.5633	0.2741	0.050*
C6	0.21521 (16)	0.7020 (3)	0.34530 (6)	0.0343 (3)
C7	0.09745 (16)	0.8962 (3)	0.36722 (6)	0.0371 (3)
C8	0.29243 (17)	1.0222 (3)	0.44833 (6)	0.0359 (3)
C9	0.03023 (19)	1.2458 (4)	0.44098 (7)	0.0499 (4)
H9A	0.0786	1.3429	0.4745	0.075*
H9B	−0.0632	1.1502	0.4536	0.075*
H9C	0.0002	1.3743	0.4099	0.075*
C10	0.63640 (19)	0.4454 (4)	0.38882 (8)	0.0536 (4)
H10A	0.6956	0.3027	0.3698	0.080*
H10B	0.6206	0.3963	0.4299	0.080*
H10C	0.6950	0.6150	0.3874	0.080*
N1	0.14501 (13)	1.0469 (2)	0.41799 (5)	0.0374 (3)
H1	0.486 (2)	0.829 (3)	0.4482 (8)	0.056 (5)*
N2	0.39514 (14)	0.8334 (2)	0.42650 (5)	0.0368 (3)
O1	−0.03642 (13)	0.9286 (3)	0.34450 (5)	0.0551 (4)
O2	0.32575 (13)	1.1631 (2)	0.49285 (5)	0.0510 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0322 (7)	0.0340 (6)	0.0292 (6)	−0.0020 (5)	−0.0025 (5)	0.0018 (5)
C2	0.0353 (7)	0.0401 (7)	0.0378 (7)	0.0022 (6)	0.0001 (6)	0.0014 (6)
C3	0.0483 (9)	0.0425 (8)	0.0404 (8)	0.0021 (7)	0.0063 (6)	−0.0053 (6)
C4	0.0548 (9)	0.0472 (8)	0.0354 (7)	−0.0065 (7)	−0.0019 (7)	−0.0077 (6)
C5	0.0393 (8)	0.0504 (8)	0.0355 (7)	−0.0073 (7)	−0.0088 (6)	0.0019 (6)
C6	0.0329 (7)	0.0372 (7)	0.0324 (7)	−0.0013 (6)	−0.0040 (5)	0.0042 (5)
C7	0.0321 (7)	0.0425 (7)	0.0361 (7)	−0.0007 (6)	−0.0069 (5)	0.0052 (6)
C8	0.0321 (7)	0.0410 (7)	0.0343 (7)	0.0042 (6)	−0.0046 (5)	−0.0005 (6)
C9	0.0401 (8)	0.0572 (9)	0.0522 (9)	0.0160 (7)	0.0007 (7)	−0.0022 (8)
C10	0.0378 (8)	0.0624 (10)	0.0599 (10)	0.0144 (8)	−0.0063 (7)	−0.0102 (8)
N1	0.0291 (6)	0.0434 (6)	0.0393 (6)	0.0069 (5)	−0.0045 (5)	0.0007 (5)
N2	0.0306 (6)	0.0436 (6)	0.0356 (6)	0.0068 (5)	−0.0081 (5)	−0.0050 (5)
O1	0.0362 (6)	0.0710 (8)	0.0566 (7)	0.0086 (5)	−0.0182 (5)	−0.0021 (6)
O2	0.0438 (6)	0.0614 (7)	0.0467 (6)	0.0140 (5)	−0.0139 (5)	−0.0198 (5)

C1—N2	1.3901 (17)	C7—N1	1.3938 (17)
C1—C6	1.4005 (18)	C8—O2	1.2291 (17)
C1—C2	1.4049 (19)	C8—N2	1.3588 (18)
C2—C3	1.381 (2)	C8—N1	1.3891 (17)
C2—C10	1.5099 (19)	C9—N1	1.4675 (19)
C3—C4	1.395 (2)	C9—H9A	0.9600
C3—H3	0.9300	C9—H9B	0.9600
C4—C5	1.361 (2)	C9—H9C	0.9600
C4—H4	0.9300	C10—H10A	0.9600
C5—C6	1.395 (2)	C10—H10B	0.9600
C5—H5	0.9300	C10—H10C	0.9600
C6—C7	1.461 (2)	N2—H1	0.888 (19)
C7—O1	1.2217 (16)
N2—C1—C6	118.44 (12)	O2—C8—N2	122.52 (12)
N2—C1—C2	121.04 (11)	O2—C8—N1	121.05 (13)
C6—C1—C2	120.52 (12)	N2—C8—N1	116.43 (11)
C3—C2—C1	117.16 (13)	N1—C9—H9A	109.5
C3—C2—C10	121.54 (13)	N1—C9—H9B	109.5
C1—C2—C10	121.29 (12)	H9A—C9—H9B	109.5
C2—C3—C4	122.73 (14)	N1—C9—H9C	109.5
C2—C3—H3	118.6	H9A—C9—H9C	109.5
C4—C3—H3	118.6	H9B—C9—H9C	109.5
C5—C4—C3	119.49 (13)	C2—C10—H10A	109.5
C5—C4—H4	120.3	C2—C10—H10B	109.5
C3—C4—H4	120.3	H10A—C10—H10B	109.5
C4—C5—C6	120.07 (13)	C2—C10—H10C	109.5
C4—C5—H5	120.0	H10A—C10—H10C	109.5
C6—C5—H5	120.0	H10B—C10—H10C	109.5
C5—C6—C1	120.02 (13)	C8—N1—C7	124.86 (11)
C5—C6—C7	120.04 (12)	C8—N1—C9	117.83 (12)
C1—C6—C7	119.92 (12)	C7—N1—C9	117.31 (11)
O1—C7—N1	119.92 (13)	C8—N2—C1	124.52 (11)
O1—C7—C6	124.26 (13)	C8—N2—H1	111.4 (11)
N1—C7—C6	115.81 (11)	C1—N2—H1	124.1 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1···O2i	0.888 (19)	2.011 (19)	2.8931 (17)	171.8 (17)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1⋯O2i	0.888 (19)	2.011 (19)	2.8931 (17)	171.8 (17)

Symmetry code: (i) .