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Acta Cryst. (2008). E64, o1677    [ doi:10.1107/S1600536808024240 ]

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

G. Liu

Abstract top

In the title compound, C8H6N2O2, intermolecular N-H...O hydrogen bonds involving the amine and carbonyl groups create centrosymmetric dimers between adjacent nearly coplanar molecules. These dimers are further connected by weak N-H...O hydrogen bonds, forming a two-dimensional network. Molecules 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 intermolecular face-to-face [pi]-[pi] stacking interactions.

Comment top

2,4(1H,3H)-Quinazolinedione derivatives are of interest because of their biological activity, and they have been widely used as key structures in medicinal drugs (Goto et al., 1993; Mohri, 2001; Mizuno et al., 2007). We herein report the crystal structure of the title compound (I). In the molecule (Fig. 1), the bond lengths and angles are within normal ranges. Intermolecular N—H···O hydrogen bonds involving amine NH and carbonyl groups O atoms form a two dimensional network (Table 1 and Fig. 2). Weak π–π stacking interactions are also observed in the crystal structure.

Related literature top

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

Experimental top

To a 100-ml, 3-necked flask equipped with condenser, were added 2-aminobenzonitrile (5.91 g, 50 mmol) and 1,8-diazabicyclo(5.4.0)undec-7-ene (DBU, 1.50 ml, 10 mmol) under argon, together with a large magnetic stirring bar. Then, CO2 (1 bar) was charged at 293 K. The mixture was vigorously stirred under CO2 (1 bar) at 423 K for 4 h. The resulting white solid was then poured into 1 M HCl (100 ml) and washed with t-BuOMe (200 ml) to give pure (I). Single crystals of (I) were obtained from a water solution, at room temperature, by slow evaporation.

Refinement top

All H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms, with N—H = 0.86 Å, C—H = 0.93 Å, and with Uiso(H) = 1.2Ueq(parent atom).

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); 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 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of the title compound with 30% displacement probability ellipsoids.
[Figure 2] Fig. 2. Two dimensional sheet formed by hydrogen bonds (dashed lines) in the title compound.
Quinazoline-2,4(1H,3H)-dione top
Crystal data top
C8H6N2O2F000 = 336
Mr = 162.15Dx = 1.495 Mg m−3
Monoclinic, P21/cMo Kα radiation
λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 5473 reflections
a = 10.891 (2) Åθ = 3.3–27.5º
b = 5.2810 (11) ŵ = 0.11 mm−1
c = 12.701 (3) ÅT = 293 (1) K
β = 99.61 (3)ºBlock, colorless
V = 720.2 (3) Å30.20 × 0.18 × 0.15 mm
Z = 4
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer		869 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.051
Monochromator: graphiteθmax = 25.0º
T = 293(1) Kθmin = 3.3º
ω scansh = −12→12
Absorption correction: nonek = −6→6
5683 measured reflectionsl = −15→15
1262 independent reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-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 = 1.07Δρmax = 0.12 e Å−3
1262 reflectionsΔρmin = −0.12 e Å−3
110 parametersExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.009 (3)
Secondary atom site location: difference Fourier map
Crystal data top
C8H6N2O2V = 720.2 (3) Å3
Mr = 162.15Z = 4
Monoclinic, P21/cMo Kα
a = 10.891 (2) ŵ = 0.11 mm−1
b = 5.2810 (11) ÅT = 293 (1) K
c = 12.701 (3) Å0.20 × 0.18 × 0.15 mm
β = 99.61 (3)º
Data collection top
Rigaku R-AXIS RAPID-S
diffractometer		1262 independent reflections
Absorption correction: none869 reflections with I > 2σ(I)
5683 measured reflectionsRint = 0.051
Refinement top
R[F2 > 2σ(F2)] = 0.055110 parameters
wR(F2) = 0.103H-atom parameters constrained
S = 1.07Δρmax = 0.12 e Å−3
1262 reflectionsΔρmin = −0.12 e Å−3
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2762 (2)0.9421 (4)0.57398 (17)0.0395 (6)
N10.11953 (17)1.0471 (4)0.67998 (14)0.0453 (6)
H1A0.08661.01760.73570.054*
O1−0.01889 (16)1.3655 (3)0.62957 (12)0.0546 (5)
C20.3772 (2)0.7919 (5)0.5574 (2)0.0494 (7)
H2A0.41480.81900.49770.059*
N20.12516 (17)1.2702 (4)0.52514 (14)0.0442 (6)
H2B0.09241.38420.48090.053*
O20.26963 (17)1.2019 (3)0.41910 (13)0.0633 (6)
C30.4210 (2)0.6050 (5)0.6289 (2)0.0560 (8)
H3A0.48840.50600.61790.067*
C40.3646 (2)0.5637 (5)0.7176 (2)0.0540 (7)
H4A0.39430.43590.76550.065*
C50.2655 (2)0.7091 (5)0.7357 (2)0.0502 (7)
H5A0.22870.68090.79560.060*
C60.2210 (2)0.8984 (4)0.66362 (17)0.0388 (6)
C70.0702 (2)1.2336 (5)0.61374 (18)0.0419 (6)
C80.2277 (2)1.1435 (5)0.49911 (18)0.0444 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0414 (14)0.0406 (14)0.0384 (13)−0.0030 (12)0.0121 (11)−0.0038 (12)
N10.0517 (13)0.0533 (13)0.0344 (11)0.0086 (11)0.0179 (10)0.0109 (10)
O10.0556 (11)0.0681 (13)0.0450 (10)0.0219 (10)0.0221 (8)0.0109 (9)
C20.0500 (16)0.0520 (17)0.0499 (16)0.0001 (14)0.0191 (13)−0.0075 (14)
N20.0538 (13)0.0474 (13)0.0346 (11)0.0079 (10)0.0169 (10)0.0077 (10)
O20.0853 (14)0.0669 (13)0.0469 (10)0.0062 (11)0.0380 (10)0.0071 (10)
C30.0486 (16)0.0527 (17)0.0670 (19)0.0098 (14)0.0107 (15)−0.0099 (16)
C40.0556 (17)0.0519 (17)0.0532 (16)0.0063 (14)0.0049 (14)0.0017 (14)
C50.0523 (16)0.0550 (17)0.0445 (15)0.0044 (14)0.0117 (12)0.0057 (13)
C60.0385 (14)0.0404 (14)0.0378 (13)−0.0006 (12)0.0077 (11)−0.0037 (12)
C70.0456 (15)0.0482 (15)0.0336 (13)0.0018 (13)0.0118 (12)0.0019 (12)
C80.0547 (17)0.0442 (15)0.0379 (14)−0.0022 (13)0.0181 (12)−0.0070 (12)
Geometric parameters (Å, °) top
C1—C61.393 (3)N2—C81.389 (3)
C1—C21.401 (3)N2—H2B0.8600
C1—C81.465 (3)O2—C81.221 (3)
N1—C71.348 (3)C3—C41.388 (3)
N1—C61.399 (3)C3—H3A0.9300
N1—H1A0.8600C4—C51.375 (3)
O1—C71.238 (3)C4—H4A0.9300
C2—C31.372 (3)C5—C61.387 (3)
C2—H2A0.9300C5—H5A0.9300
N2—C71.373 (3)
C6—C1—C2119.1 (2)C5—C4—C3120.9 (3)
C6—C1—C8119.6 (2)C5—C4—H4A119.5
C2—C1—C8121.3 (2)C3—C4—H4A119.5
C7—N1—C6124.0 (2)C4—C5—C6119.3 (2)
C7—N1—H1A118.0C4—C5—H5A120.3
C6—N1—H1A118.0C6—C5—H5A120.3
C3—C2—C1120.2 (2)C5—C6—C1120.5 (2)
C3—C2—H2A119.9C5—C6—N1120.3 (2)
C1—C2—H2A119.9C1—C6—N1119.2 (2)
C7—N2—C8127.2 (2)O1—C7—N1123.4 (2)
C7—N2—H2B116.4O1—C7—N2121.0 (2)
C8—N2—H2B116.4N1—C7—N2115.6 (2)
C2—C3—C4119.9 (2)O2—C8—N2120.2 (2)
C2—C3—H3A120.0O2—C8—C1125.4 (2)
C4—C3—H3A120.0N2—C8—C1114.3 (2)
C6—C1—C2—C3−0.1 (4)C7—N1—C6—C10.0 (3)
C8—C1—C2—C3179.8 (2)C6—N1—C7—O1−179.3 (2)
C1—C2—C3—C40.3 (4)C6—N1—C7—N20.9 (3)
C2—C3—C4—C5−0.5 (4)C8—N2—C7—O1177.6 (2)
C3—C4—C5—C60.4 (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—N1179.4 (2)C7—N2—C8—C13.1 (3)
C2—C1—C6—C50.1 (3)C6—C1—C8—O2178.7 (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—N10.4 (3)C2—C1—C8—N2178.2 (2)
C7—N1—C6—C5−179.7 (2)
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O1i0.862.002.854176
N1—H1A···O1ii0.862.132.976168
Symmetry codes: (i) −x, −y+3, −z+1; (ii) −x, y−1/2, −z+3/2.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
N2—H2B···O1i0.862.002.854176
N1—H1A···O1ii0.862.132.976168
Symmetry codes: (i) −x, −y+3, −z+1; (ii) −x, y−1/2, −z+3/2.
Acknowledgements top

The author thanks Chifeng University for supporting this work.

references
References top

Goto, S., Tsuboi, H. & Kagara, K. (1993). Chem. Express, 8, 761–764.

Mizuno, T., Mihara, M., Nakai, T., Iwai, T. & Ito, T. (2007). Synthesis, pp. 2524–2528.

Mohri, S. J. (2001). Synth. Org. Chem. Jpn, 59, 514–515.

Rigaku (1998). RAPID-AUTO. Rigaku Corporation,Tokyo, Japan.

Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC,The Woodlands, Texas, USA.

Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122.