7-Nitro-quinazolin-4(3H)-one.

In the crystal structure of the title compound, C(8)H(5)N(3)O(3), inter-molecular N-H⋯O hydrogen bonds link mol-ecules into centrosymmetric dimers. These dimers are, in turn, linked though weak inter-molecular C-H⋯O and C-H⋯N hydrogen bonds and π-π stacking inter-actions, with centroid-centroid distances of 3.678 (3) Å, into a three-dimensional network.

Related literature

For related literature on biological activity, see: Masanori et al. (2003 ▶); Wolfe et al. (1990 ▶). For related structures, see: Chadwick & Easton (1983 ▶); Etter (1983 ▶).

Experimental

Crystal data

C8H5N3O3

M = 191.15

Monoclinic,

a = 5.1063 (10) Å

b = 11.206 (2) Å

c = 13.528 (3) Å

β = 99.19 (3)°

V = 764.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.13 mm−1

T = 153 (2) K

0.24 × 0.18 × 0.16 mm

Data collection

Rigaku R-AXIS RAPID IP area-detector diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.969, T max = 0.979

5749 measured reflections

1340 independent reflections

1215 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.096

S = 1.11

1340 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.31 e Å−3

Data collection: RAPID-AUTO (Rigaku, 2004 ▶); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXTL (Sheldrick, 2001 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807062666/lh2576sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536807062666/lh2576Isup2.hkl

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

C8H5N3O3	F000 = 392
Mr = 191.15	Dx = 1.662 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6207 reflections
a = 5.1063 (10) Å	θ = 6.0–55.0º
b = 11.206 (2) Å	µ = 0.13 mm−1
c = 13.528 (3) Å	T = 153 (2) K
β = 99.19 (3)º	Needle, colorless
V = 764.1 (3) Å3	0.24 × 0.18 × 0.16 mm
Z = 4

Rigaku R-AXIS RAPID IP area-detector diffractometer	1340 independent reflections
Radiation source: Rotating Anode	1215 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.021
T = 153(2) K	θmax = 25.0º
ω Oscillation scans	θmin = 3.1º
Absorption correction: multi-scan(ABSCOR; Higashi, 1995)	h = −6→6
Tmin = 0.969, Tmax = 0.979	k = −13→13
5749 measured reflections	l = −16→15

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)] = 0.034	H-atom parameters constrained
wR(F2) = 0.096	w = 1/[σ2(Fo2) + (0.064P)2 + 0.0923P] where P = (Fo2 + 2Fc2)/3
S = 1.11	(Δ/σ)max < 0.001
1340 reflections	Δρmax = 0.15 e Å−3
127 parameters	Δρmin = −0.31 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	−0.37255 (17)	0.37262 (8)	0.24708 (6)	0.0228 (3)
O2	−0.1637 (2)	0.51746 (9)	0.33145 (8)	0.0324 (3)
O3	0.69259 (17)	−0.00398 (7)	0.41669 (6)	0.0203 (3)
N1	0.6334 (2)	0.33230 (10)	0.53066 (8)	0.0214 (3)
N2	0.8443 (2)	0.14538 (9)	0.52489 (7)	0.0183 (3)
H2A	0.9807	0.1015	0.5512	0.022*
C1	0.8209 (2)	0.25752 (11)	0.56195 (9)	0.0206 (3)
H1B	0.9536	0.2827	0.6152	0.025*
C2	0.6655 (2)	0.09785 (11)	0.44863 (8)	0.0163 (3)
C3	0.4471 (2)	0.17821 (10)	0.40975 (8)	0.0160 (3)
C4	0.2491 (2)	0.14293 (11)	0.33110 (9)	0.0188 (3)
H4A	0.2557	0.0658	0.3025	0.023*
C5	0.0451 (2)	0.21960 (11)	0.29509 (9)	0.0194 (3)
H5A	−0.0904	0.1964	0.2421	0.023*
C6	0.0434 (2)	0.33253 (11)	0.33893 (9)	0.0171 (3)
C7	0.2345 (2)	0.37169 (11)	0.41533 (9)	0.0176 (3)
H7A	0.2274	0.4498	0.4421	0.021*
C8	0.4409 (2)	0.29261 (11)	0.45270 (8)	0.0166 (3)
N3	−0.17982 (19)	0.41378 (10)	0.30265 (7)	0.0194 (3)

	U11	U22	U33	U12	U13	U23
O1	0.0179 (5)	0.0261 (6)	0.0224 (5)	−0.0023 (4)	−0.0028 (3)	0.0042 (3)
O2	0.0344 (6)	0.0166 (5)	0.0416 (6)	0.0077 (4)	−0.0086 (4)	−0.0043 (4)
O3	0.0219 (5)	0.0143 (5)	0.0248 (5)	0.0033 (4)	0.0043 (3)	−0.0018 (3)
N1	0.0228 (6)	0.0167 (6)	0.0227 (5)	0.0021 (4)	−0.0023 (4)	−0.0026 (4)
N2	0.0167 (5)	0.0155 (6)	0.0219 (5)	0.0034 (4)	0.0003 (4)	0.0017 (4)
C1	0.0225 (7)	0.0170 (7)	0.0208 (6)	0.0016 (5)	−0.0005 (5)	−0.0008 (4)
C2	0.0170 (6)	0.0146 (7)	0.0183 (6)	−0.0009 (5)	0.0062 (4)	0.0020 (4)
C3	0.0171 (6)	0.0146 (7)	0.0174 (6)	−0.0001 (5)	0.0056 (4)	0.0017 (4)
C4	0.0208 (7)	0.0145 (7)	0.0217 (6)	−0.0011 (5)	0.0049 (5)	−0.0034 (5)
C5	0.0192 (6)	0.0196 (7)	0.0185 (6)	−0.0032 (5)	0.0010 (4)	−0.0011 (5)
C6	0.0165 (6)	0.0156 (6)	0.0195 (6)	0.0014 (5)	0.0036 (4)	0.0033 (5)
C7	0.0201 (7)	0.0127 (6)	0.0199 (6)	0.0010 (5)	0.0033 (5)	−0.0006 (4)
C8	0.0182 (6)	0.0150 (6)	0.0168 (6)	−0.0016 (5)	0.0034 (4)	0.0009 (5)
N3	0.0192 (6)	0.0191 (6)	0.0197 (5)	0.0013 (4)	0.0020 (4)	0.0037 (4)

O1—N3	1.2289 (14)	C3—C4	1.4023 (17)
O2—N3	1.2240 (15)	C3—C8	1.4099 (17)
O3—C2	1.2358 (15)	C4—C5	1.3779 (18)
N1—C1	1.2916 (17)	C4—H4A	0.9500
N1—C8	1.3946 (16)	C5—C6	1.3982 (18)
N2—C1	1.3652 (16)	C5—H5A	0.9500
N2—C2	1.3713 (16)	C6—C7	1.3750 (17)
N2—H2A	0.8800	C6—N3	1.4799 (16)
C1—H1B	0.9500	C7—C8	1.4076 (18)
C2—C3	1.4644 (17)	C7—H7A	0.9500
C1—N1—C8	115.91 (11)	C4—C5—C6	118.03 (11)
C1—N2—C2	123.16 (10)	C4—C5—H5A	121.0
C1—N2—H2A	118.4	C6—C5—H5A	121.0
C2—N2—H2A	118.4	C7—C6—C5	123.78 (11)
N1—C1—N2	125.49 (11)	C7—C6—N3	118.00 (11)
N1—C1—H1B	117.3	C5—C6—N3	118.21 (11)
N2—C1—H1B	117.3	C6—C7—C8	118.02 (11)
O3—C2—N2	121.57 (11)	C6—C7—H7A	121.0
O3—C2—C3	124.30 (11)	C8—C7—H7A	121.0
N2—C2—C3	114.12 (11)	N1—C8—C7	117.89 (11)
C4—C3—C8	120.54 (11)	N1—C8—C3	122.83 (11)
C4—C3—C2	120.97 (11)	C7—C8—C3	119.28 (11)
C8—C3—C2	118.49 (11)	O2—N3—O1	123.89 (10)
C5—C4—C3	120.34 (11)	O2—N3—C6	117.99 (10)
C5—C4—H4A	119.8	O1—N3—C6	118.10 (10)
C3—C4—H4A	119.8
C8—N1—C1—N2	0.28 (19)	N3—C6—C7—C8	177.39 (10)
C2—N2—C1—N1	−0.5 (2)	C1—N1—C8—C7	−179.22 (11)
C1—N2—C2—O3	179.92 (11)	C1—N1—C8—C3	0.03 (18)
C1—N2—C2—C3	0.33 (16)	C6—C7—C8—N1	−179.57 (10)
O3—C2—C3—C4	−0.08 (19)	C6—C7—C8—C3	1.15 (17)
N2—C2—C3—C4	179.50 (10)	C4—C3—C8—N1	−179.68 (11)
O3—C2—C3—C8	−179.62 (10)	C2—C3—C8—N1	−0.14 (17)
N2—C2—C3—C8	−0.04 (16)	C4—C3—C8—C7	−0.44 (18)
C8—C3—C4—C5	−0.31 (18)	C2—C3—C8—C7	179.10 (10)
C2—C3—C4—C5	−179.83 (11)	C7—C6—N3—O2	10.75 (16)
C3—C4—C5—C6	0.30 (18)	C5—C6—N3—O2	−170.57 (11)
C4—C5—C6—C7	0.47 (19)	C7—C6—N3—O1	−167.81 (10)
C4—C5—C6—N3	−178.12 (10)	C5—C6—N3—O1	10.87 (16)
C5—C6—C7—C8	−1.21 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O3i	0.88	1.98	2.8514 (14)	169
C1—H1B···O2ii	0.95	2.54	3.2703 (17)	134
C1—H1B···O1iii	0.95	2.55	3.0978 (17)	117
C5—H5A···O2iv	0.95	2.49	3.2846 (16)	142
C7—H7A···N1ii	0.95	2.55	3.4402 (18)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O3i	0.88	1.98	2.8514 (14)	169
C1—H1B⋯O2ii	0.95	2.54	3.2703 (17)	134
C1—H1B⋯O1iii	0.95	2.55	3.0978 (17)	117
C5—H5A⋯O2iv	0.95	2.49	3.2846 (16)	142
C7—H7A⋯N1ii	0.95	2.55	3.4402 (18)	155

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .