Quinazoline-2,4(1H,3H)-dione.

In the title compound, C(8)H(6)N(2)O(2), inter-molecular N-H⋯O hydrogen bonds involving the amine and carbonyl groups create centrosymmetric dimers between adjacent nearly coplanar mol-ecules. These dimers are further connected by weak N-H⋯O hydrogen bonds, forming a two-dimensional network. Mol-ecules are packed in the crystal structure with adjacent benzene and pyrimidine rings approximately coplanar; the centroid-centroid separation is 3.863 Å and the dihedral angle between the mean planes is 0.64°, indicating the presence of weak inter-molecular face-to-face π-π stacking inter-actions.

Related literature

For background, see: Goto et al. (1993 ▶); Mohri (2001 ▶); For further synthetic details, see: Mizuno et al. (2007 ▶).

Experimental

Crystal data

C8H6N2O2

M = 162.15

Monoclinic,

a = 10.891 (2) Å

b = 5.2810 (11) Å

c = 12.701 (3) Å

β = 99.61 (3)°

V = 720.2 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 (1) K

0.20 × 0.18 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: none

5683 measured reflections

1262 independent reflections

869 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.055

wR(F 2) = 0.103

S = 1.06

1262 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.12 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808024240/bh2183sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024240/bh2183Isup2.hkl

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

C8H6N2O2	F000 = 336
Mr = 162.15	Dx = 1.495 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5473 reflections
a = 10.891 (2) Å	θ = 3.3–27.5º
b = 5.2810 (11) Å	µ = 0.11 mm−1
c = 12.701 (3) Å	T = 293 (1) K
β = 99.61 (3)º	Block, colorless
V = 720.2 (3) Å3	0.20 × 0.18 × 0.15 mm
Z = 4

Rigaku R-AXIS RAPID-S diffractometer	869 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.051
Monochromator: graphite	θmax = 25.0º
T = 293(1) K	θmin = 3.3º
ω scans	h = −12→12
Absorption correction: none	k = −6→6
5683 measured reflections	l = −15→15
1262 independent reflections

Refinement on F2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F2 > 2σ(F2)] = 0.055	w = 1/[σ2(Fo2) + (0.0327P)2 + 0.2501P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.103	(Δ/σ)max = 0.004
S = 1.07	Δρmax = 0.12 e Å−3
1262 reflections	Δρmin = −0.12 e Å−3
110 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.009 (3)
Secondary atom site location: difference Fourier map

	x	y	z	Uiso*/Ueq
C1	0.2762 (2)	0.9421 (4)	0.57398 (17)	0.0395 (6)
N1	0.11953 (17)	1.0471 (4)	0.67998 (14)	0.0453 (6)
H1A	0.0866	1.0176	0.7357	0.054*
O1	−0.01889 (16)	1.3655 (3)	0.62957 (12)	0.0546 (5)
C2	0.3772 (2)	0.7919 (5)	0.5574 (2)	0.0494 (7)
H2A	0.4148	0.8190	0.4977	0.059*
N2	0.12516 (17)	1.2702 (4)	0.52514 (14)	0.0442 (6)
H2B	0.0924	1.3842	0.4809	0.053*
O2	0.26963 (17)	1.2019 (3)	0.41910 (13)	0.0633 (6)
C3	0.4210 (2)	0.6050 (5)	0.6289 (2)	0.0560 (8)
H3A	0.4884	0.5060	0.6179	0.067*
C4	0.3646 (2)	0.5637 (5)	0.7176 (2)	0.0540 (7)
H4A	0.3943	0.4359	0.7655	0.065*
C5	0.2655 (2)	0.7091 (5)	0.7357 (2)	0.0502 (7)
H5A	0.2287	0.6809	0.7956	0.060*
C6	0.2210 (2)	0.8984 (4)	0.66362 (17)	0.0388 (6)
C7	0.0702 (2)	1.2336 (5)	0.61374 (18)	0.0419 (6)
C8	0.2277 (2)	1.1435 (5)	0.49911 (18)	0.0444 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0414 (14)	0.0406 (14)	0.0384 (13)	−0.0030 (12)	0.0121 (11)	−0.0038 (12)
N1	0.0517 (13)	0.0533 (13)	0.0344 (11)	0.0086 (11)	0.0179 (10)	0.0109 (10)
O1	0.0556 (11)	0.0681 (13)	0.0450 (10)	0.0219 (10)	0.0221 (8)	0.0109 (9)
C2	0.0500 (16)	0.0520 (17)	0.0499 (16)	0.0001 (14)	0.0191 (13)	−0.0075 (14)
N2	0.0538 (13)	0.0474 (13)	0.0346 (11)	0.0079 (10)	0.0169 (10)	0.0077 (10)
O2	0.0853 (14)	0.0669 (13)	0.0469 (10)	0.0062 (11)	0.0380 (10)	0.0071 (10)
C3	0.0486 (16)	0.0527 (17)	0.0670 (19)	0.0098 (14)	0.0107 (15)	−0.0099 (16)
C4	0.0556 (17)	0.0519 (17)	0.0532 (16)	0.0063 (14)	0.0049 (14)	0.0017 (14)
C5	0.0523 (16)	0.0550 (17)	0.0445 (15)	0.0044 (14)	0.0117 (12)	0.0057 (13)
C6	0.0385 (14)	0.0404 (14)	0.0378 (13)	−0.0006 (12)	0.0077 (11)	−0.0037 (12)
C7	0.0456 (15)	0.0482 (15)	0.0336 (13)	0.0018 (13)	0.0118 (12)	0.0019 (12)
C8	0.0547 (17)	0.0442 (15)	0.0379 (14)	−0.0022 (13)	0.0181 (12)	−0.0070 (12)

C1—C6	1.393 (3)	N2—C8	1.389 (3)
C1—C2	1.401 (3)	N2—H2B	0.8600
C1—C8	1.465 (3)	O2—C8	1.221 (3)
N1—C7	1.348 (3)	C3—C4	1.388 (3)
N1—C6	1.399 (3)	C3—H3A	0.9300
N1—H1A	0.8600	C4—C5	1.375 (3)
O1—C7	1.238 (3)	C4—H4A	0.9300
C2—C3	1.372 (3)	C5—C6	1.387 (3)
C2—H2A	0.9300	C5—H5A	0.9300
N2—C7	1.373 (3)
C6—C1—C2	119.1 (2)	C5—C4—C3	120.9 (3)
C6—C1—C8	119.6 (2)	C5—C4—H4A	119.5
C2—C1—C8	121.3 (2)	C3—C4—H4A	119.5
C7—N1—C6	124.0 (2)	C4—C5—C6	119.3 (2)
C7—N1—H1A	118.0	C4—C5—H5A	120.3
C6—N1—H1A	118.0	C6—C5—H5A	120.3
C3—C2—C1	120.2 (2)	C5—C6—C1	120.5 (2)
C3—C2—H2A	119.9	C5—C6—N1	120.3 (2)
C1—C2—H2A	119.9	C1—C6—N1	119.2 (2)
C7—N2—C8	127.2 (2)	O1—C7—N1	123.4 (2)
C7—N2—H2B	116.4	O1—C7—N2	121.0 (2)
C8—N2—H2B	116.4	N1—C7—N2	115.6 (2)
C2—C3—C4	119.9 (2)	O2—C8—N2	120.2 (2)
C2—C3—H3A	120.0	O2—C8—C1	125.4 (2)
C4—C3—H3A	120.0	N2—C8—C1	114.3 (2)
C6—C1—C2—C3	−0.1 (4)	C7—N1—C6—C1	0.0 (3)
C8—C1—C2—C3	179.8 (2)	C6—N1—C7—O1	−179.3 (2)
C1—C2—C3—C4	0.3 (4)	C6—N1—C7—N2	0.9 (3)
C2—C3—C4—C5	−0.5 (4)	C8—N2—C7—O1	177.6 (2)
C3—C4—C5—C6	0.4 (4)	C8—N2—C7—N1	−2.7 (3)
C4—C5—C6—C1	−0.3 (4)	C7—N2—C8—O2	−177.4 (2)
C4—C5—C6—N1	179.4 (2)	C7—N2—C8—C1	3.1 (3)
C2—C1—C6—C5	0.1 (3)	C6—C1—C8—O2	178.7 (2)
C8—C1—C6—C5	−179.9 (2)	C2—C1—C8—O2	−1.3 (4)
C2—C1—C6—N1	−179.6 (2)	C6—C1—C8—N2	−1.8 (3)
C8—C1—C6—N1	0.4 (3)	C2—C1—C8—N2	178.2 (2)
C7—N1—C6—C5	−179.7 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2B···O1i	0.86	2.00	2.854	176
N1—H1A···O1ii	0.86	2.13	2.976	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2B⋯O1i	0.86	2.00	2.854	176
N1—H1A⋯O1ii	0.86	2.13	2.976	168

Symmetry codes: (i) ; (ii) .