7-Fluoro-6-nitro-quinazolin-4(3H)-one.

The quinazolinone unit of the title compound, C(8)H(4)FN(3)O(3), is essentially planar, with a maximum deviation of 0.0538 (14) Å for the O atom. The nitro group is twisted by 12.0 (3)° from the mean plane of the quinazolinone ring system. The crystal structure is stabilized by inter-molecular N-H⋯O, C-H⋯N and C-H⋯O hydrogen bonds.

Related literature

The title compound is used as an inter­mediate for the production of several multi-targeted Raf kinase inhibitors, such as 4(3H)-quinazolinone and its derivatives, see: Bridges et al. (1996 ▶); Kim et al. (2008 ▶). For the anti­tumor activities of quinolines, see: Labuda et al. (2009 ▶). For synthetic aspects, see: Rewcastle et al. (1996 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C8H4FN3O3

M = 209.14

Triclinic,

a = 5.6360 (11) Å

b = 8.409 (2) Å

c = 8.674 (2) Å

α = 79.38 (3)°

β = 89.23 (3)°

γ = 83.83 (3)°

V = 401.70 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.15 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.956, T max = 0.971

1623 measured reflections

1461 independent reflections

1131 reflections with I > 2σ(I)

R int = 0.018

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.160

S = 1.00

1461 reflections

137 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.25 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809046984/pv2231sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809046984/pv2231Isup2.hkl

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

C8H4FN3O3	Z = 2
Mr = 209.14	F(000) = 212
Triclinic, P1	Dx = 1.729 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.6360 (11) Å	Cell parameters from 25 reflections
b = 8.409 (2) Å	θ = 9–13°
c = 8.674 (2) Å	µ = 0.15 mm−1
α = 79.38 (3)°	T = 293 K
β = 89.23 (3)°	Block, colorless
γ = 83.83 (3)°	0.30 × 0.20 × 0.20 mm
V = 401.70 (16) Å3

Enraf–Nonius CAD-4 diffractometer	1131 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.018
graphite	θmax = 25.3°, θmin = 2.4°
ω/2θ scans	h = 0→6
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.956, Tmax = 0.971	l = −10→10
1623 measured reflections	3 standard reflections every 200 reflections
1461 independent reflections	intensity decay: 1%

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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.160	w = 1/[σ2(Fo2) + (0.1P)2 + 0.12P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1461 reflections	Δρmax = 0.23 e Å−3
137 parameters	Δρmin = −0.25 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.062 (16)

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
F	0.1138 (3)	0.4301 (2)	−0.33786 (16)	0.0639 (5)
N1	0.1677 (3)	0.1637 (2)	0.3773 (2)	0.0413 (5)
H1A	0.1629	0.1209	0.4752	0.050*
O1	−0.1399 (3)	0.0293 (2)	0.32253 (18)	0.0527 (6)
C1	0.3360 (4)	0.2651 (3)	0.3291 (3)	0.0419 (6)
H1B	0.4402	0.2828	0.4049	0.050*
N2	0.3644 (3)	0.3390 (2)	0.1878 (2)	0.0406 (5)
C2	0.0044 (4)	0.1261 (3)	0.2775 (2)	0.0380 (6)
O2	−0.2795 (5)	0.3272 (3)	−0.3951 (2)	0.0932 (9)
C3	0.0261 (4)	0.2086 (2)	0.1159 (2)	0.0331 (5)
N3	−0.2740 (4)	0.2376 (3)	−0.2685 (2)	0.0486 (6)
O3	−0.4036 (3)	0.1313 (2)	−0.2327 (2)	0.0630 (6)
C4	−0.1305 (4)	0.1862 (3)	0.0011 (3)	0.0376 (6)
H4A	−0.2523	0.1200	0.0276	0.045*
C5	−0.1046 (4)	0.2618 (3)	−0.1509 (3)	0.0380 (5)
C6	0.0818 (4)	0.3590 (3)	−0.1903 (2)	0.0396 (6)
C7	0.2349 (4)	0.3832 (3)	−0.0789 (3)	0.0387 (6)
H7A	0.3567	0.4491	−0.1068	0.046*
C8	0.2091 (4)	0.3091 (2)	0.0771 (2)	0.0334 (5)

	U11	U22	U33	U12	U13	U23
F	0.0696 (10)	0.0883 (11)	0.0293 (8)	−0.0238 (8)	−0.0026 (6)	0.0104 (7)
N1	0.0493 (11)	0.0479 (11)	0.0260 (9)	−0.0160 (9)	−0.0022 (8)	0.0010 (8)
O1	0.0562 (11)	0.0618 (11)	0.0393 (9)	−0.0333 (8)	−0.0015 (7)	0.0086 (8)
C1	0.0434 (13)	0.0495 (13)	0.0342 (12)	−0.0154 (10)	−0.0056 (9)	−0.0051 (10)
N2	0.0413 (10)	0.0474 (11)	0.0338 (10)	−0.0172 (8)	−0.0030 (8)	−0.0019 (8)
C2	0.0401 (12)	0.0390 (12)	0.0338 (12)	−0.0107 (9)	−0.0005 (9)	−0.0001 (9)
O2	0.1106 (19)	0.123 (2)	0.0446 (12)	−0.0476 (15)	−0.0370 (12)	0.0113 (12)
C3	0.0356 (11)	0.0321 (11)	0.0306 (11)	−0.0060 (9)	−0.0001 (8)	−0.0019 (8)
N3	0.0487 (12)	0.0573 (13)	0.0421 (12)	−0.0065 (10)	−0.0087 (9)	−0.0138 (10)
O3	0.0533 (11)	0.0733 (13)	0.0676 (13)	−0.0208 (10)	−0.0126 (9)	−0.0172 (10)
C4	0.0372 (12)	0.0385 (12)	0.0385 (12)	−0.0115 (9)	−0.0015 (9)	−0.0063 (9)
C5	0.0404 (12)	0.0403 (12)	0.0333 (11)	−0.0028 (10)	−0.0060 (9)	−0.0069 (9)
C6	0.0450 (13)	0.0434 (12)	0.0273 (11)	−0.0041 (10)	0.0026 (9)	0.0009 (9)
C7	0.0374 (12)	0.0412 (12)	0.0360 (12)	−0.0111 (9)	0.0028 (9)	0.0003 (9)
C8	0.0316 (11)	0.0358 (11)	0.0322 (11)	−0.0067 (8)	−0.0004 (8)	−0.0032 (8)

F—C6	1.328 (2)	C3—C4	1.391 (3)
N1—C1	1.354 (3)	C3—C8	1.401 (3)
N1—C2	1.371 (3)	N3—O3	1.208 (3)
N1—H1A	0.8600	N3—C5	1.462 (3)
O1—C2	1.222 (3)	C4—C5	1.367 (3)
C1—N2	1.284 (3)	C4—H4A	0.9300
C1—H1B	0.9300	C5—C6	1.401 (3)
N2—C8	1.381 (3)	C6—C7	1.361 (3)
C2—C3	1.455 (3)	C7—C8	1.394 (3)
O2—N3	1.211 (3)	C7—H7A	0.9300
C1—N1—C2	123.10 (18)	C5—C4—C3	119.7 (2)
C1—N1—H1A	118.4	C5—C4—H4A	120.1
C2—N1—H1A	118.4	C3—C4—H4A	120.1
N2—C1—N1	125.7 (2)	C4—C5—C6	119.8 (2)
N2—C1—H1B	117.2	C4—C5—N3	118.4 (2)
N1—C1—H1B	117.2	C6—C5—N3	121.8 (2)
C1—N2—C8	115.98 (18)	F—C6—C7	118.2 (2)
O1—C2—N1	121.96 (19)	F—C6—C5	120.7 (2)
O1—C2—C3	124.5 (2)	C7—C6—C5	121.1 (2)
N1—C2—C3	113.51 (19)	C6—C7—C8	120.0 (2)
C4—C3—C8	120.5 (2)	C6—C7—H7A	120.0
C4—C3—C2	120.43 (19)	C8—C7—H7A	120.0
C8—C3—C2	119.07 (19)	N2—C8—C7	118.51 (19)
O3—N3—O2	123.8 (2)	N2—C8—C3	122.58 (19)
O3—N3—C5	118.1 (2)	C7—C8—C3	118.91 (19)
O2—N3—C5	118.1 (2)
C2—N1—C1—N2	0.6 (4)	O2—N3—C5—C6	−14.0 (4)
N1—C1—N2—C8	−0.8 (4)	C4—C5—C6—F	178.24 (19)
C1—N1—C2—O1	177.0 (2)	N3—C5—C6—F	−1.5 (4)
C1—N1—C2—C3	−1.4 (3)	C4—C5—C6—C7	−1.7 (4)
O1—C2—C3—C4	3.2 (4)	N3—C5—C6—C7	178.6 (2)
N1—C2—C3—C4	−178.5 (2)	F—C6—C7—C8	−179.23 (19)
O1—C2—C3—C8	−175.9 (2)	C5—C6—C7—C8	0.7 (4)
N1—C2—C3—C8	2.5 (3)	C1—N2—C8—C7	−178.6 (2)
C8—C3—C4—C5	0.5 (3)	C1—N2—C8—C3	2.0 (3)
C2—C3—C4—C5	−178.60 (19)	C6—C7—C8—N2	−178.6 (2)
C3—C4—C5—C6	1.1 (3)	C6—C7—C8—C3	0.8 (3)
C3—C4—C5—N3	−179.19 (19)	C4—C3—C8—N2	178.01 (19)
O3—N3—C5—C4	−12.3 (3)	C2—C3—C8—N2	−2.9 (3)
O2—N3—C5—C4	166.3 (2)	C4—C3—C8—C7	−1.4 (3)
O3—N3—C5—C6	167.4 (2)	C2—C3—C8—C7	177.65 (19)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1i	0.86	1.98	2.815 (2)	165
C1—H1B···O2ii	0.93	2.47	3.396 (3)	179
C7—H7A···N2iii	0.93	2.50	3.422 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1i	0.86	1.98	2.815 (2)	165
C1—H1B⋯O2ii	0.93	2.47	3.396 (3)	179
C7—H7A⋯N2iii	0.93	2.50	3.422 (3)	171

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