4-[(7-Fluoro-quinazolin-4-yl)-oxy]aniline.

In the mol-ecule of the title compound, C(14)H(10)FN(3)O, the bicyclic quinazoline system is effectively planar, with a mean deviation from planarity of 0.0140 (3) Å. The quinazoline heterocyclic system and the adjacent benzene ring make a dihedral angle of 85.73 (9)°. Two inter-molecular N-H⋯N hydrogen bonds contribute to the stability of the crystal structure. In addition, a weak π-π stacking inter-action [centroid-centroid distance = 3.902 (2) Å] is observed.

Related literature

For general background to quinazolines, see: Labuda et al. (2009 ▶). Graves et al. (2002 ▶); For the preparation of the title compound, see: Zhang et al. (2010 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C14H10FN3O

M = 255.25

Orthorhombic,

a = 8.0210 (16) Å

b = 8.3370 (17) Å

c = 17.562 (4) Å

V = 1174.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.969, T max = 0.990

2351 measured reflections

1256 independent reflections

883 reflections with I > 2σ(I)

R int = 0.082

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.110

S = 1.02

1256 reflections

172 parameters

H-atom parameters constrained

Δρmax = 0.12 e Å−3

Δρmin = −0.15 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: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810053286/zl2317sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810053286/zl2317Isup2.hkl

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

C14H10FN3O	F(000) = 528
Mr = 255.25	Dx = 1.444 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 8.0210 (16) Å	θ = 9.0–12.0°
b = 8.3370 (17) Å	µ = 0.11 mm−1
c = 17.562 (4) Å	T = 293 K
V = 1174.4 (4) Å3	Block, colorless
Z = 4	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	883 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.082
graphite	θmax = 25.3°, θmin = 2.3°
ω/2θ scans	h = −9→0
Absorption correction: ψ scan (North et al., 1968)	k = −10→10
Tmin = 0.969, Tmax = 0.990	l = −21→0
2351 measured reflections	3 standard reflections every 200 reflections
1256 independent reflections	intensity decay: 1%

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.046P)2] where P = (Fo2 + 2Fc2)/3
1256 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.12 e Å−3
0 restraints	Δρmin = −0.15 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
F1	0.3205 (3)	0.8351 (3)	0.76958 (14)	0.0778 (8)
O1	0.4564 (4)	0.2636 (3)	0.54742 (14)	0.0600 (8)
N1	0.5255 (5)	−0.3210 (3)	0.39680 (17)	0.0613 (9)
H1A	0.6191	−0.3749	0.4060	0.074*
H1B	0.5050	−0.3230	0.3470	0.074*
N2	0.2795 (4)	0.1426 (3)	0.63318 (17)	0.0543 (9)
N3	0.1694 (4)	0.2924 (4)	0.73803 (17)	0.0558 (9)
C1	0.5944 (5)	0.0096 (4)	0.5327 (2)	0.0557 (10)
H1C	0.6622	0.0345	0.5740	0.067*
C2	0.6148 (5)	−0.1334 (4)	0.49402 (19)	0.0522 (9)
H2B	0.6978	−0.2042	0.5093	0.063*
C3	0.5145 (5)	−0.1730 (4)	0.43328 (19)	0.0449 (9)
C4	0.3965 (5)	−0.0629 (4)	0.41001 (19)	0.0527 (10)
H4A	0.3302	−0.0854	0.3679	0.063*
C5	0.3757 (5)	0.0809 (4)	0.4487 (2)	0.0564 (10)
H5A	0.2952	0.1540	0.4329	0.068*
C6	0.4732 (5)	0.1138 (4)	0.50944 (18)	0.0472 (9)
C7	0.3580 (5)	0.2687 (4)	0.60919 (19)	0.0467 (9)
C8	0.1880 (5)	0.1638 (5)	0.6966 (2)	0.0593 (11)
H8A	0.1297	0.0739	0.7132	0.071*
C9	0.2538 (4)	0.4244 (4)	0.71251 (19)	0.0444 (8)
C10	0.2435 (5)	0.5671 (4)	0.7550 (2)	0.0552 (10)
H10A	0.1805	0.5725	0.7994	0.066*
C11	0.3285 (6)	0.6964 (4)	0.7291 (2)	0.0540 (10)
C12	0.4236 (5)	0.6976 (4)	0.6636 (2)	0.0580 (10)
H12A	0.4787	0.7902	0.6481	0.070*
C13	0.4348 (5)	0.5598 (4)	0.6223 (2)	0.0520 (10)
H13A	0.4979	0.5577	0.5779	0.062*
C14	0.3511 (4)	0.4204 (4)	0.64658 (18)	0.0420 (8)

	U11	U22	U33	U12	U13	U23
F1	0.0938 (19)	0.0589 (13)	0.0808 (16)	−0.0023 (15)	−0.0035 (15)	−0.0267 (12)
O1	0.0754 (19)	0.0483 (14)	0.0565 (14)	−0.0111 (16)	0.0223 (15)	−0.0100 (12)
N1	0.070 (2)	0.0483 (17)	0.0654 (19)	0.0034 (18)	0.0088 (19)	−0.0101 (15)
N2	0.0546 (19)	0.0488 (19)	0.059 (2)	−0.0069 (17)	0.0063 (18)	0.0018 (15)
N3	0.062 (2)	0.0521 (18)	0.0539 (18)	−0.0034 (18)	0.0099 (18)	−0.0034 (16)
C1	0.057 (2)	0.061 (2)	0.049 (2)	−0.007 (2)	−0.004 (2)	0.0017 (19)
C2	0.051 (2)	0.057 (2)	0.049 (2)	0.005 (2)	−0.0010 (19)	0.0061 (18)
C3	0.048 (2)	0.0434 (19)	0.0432 (19)	−0.0021 (19)	0.0097 (18)	0.0039 (16)
C4	0.050 (2)	0.059 (2)	0.049 (2)	−0.002 (2)	−0.008 (2)	−0.0106 (19)
C5	0.059 (2)	0.051 (2)	0.059 (2)	0.007 (2)	−0.003 (2)	0.005 (2)
C6	0.057 (2)	0.0423 (19)	0.0429 (19)	−0.0055 (19)	0.009 (2)	−0.0038 (17)
C7	0.047 (2)	0.049 (2)	0.0441 (19)	−0.002 (2)	0.0011 (19)	−0.0011 (17)
C8	0.059 (2)	0.055 (2)	0.064 (2)	−0.010 (2)	0.012 (2)	0.009 (2)
C9	0.0401 (19)	0.046 (2)	0.0473 (19)	0.0028 (18)	−0.0046 (18)	0.0004 (18)
C10	0.052 (2)	0.065 (2)	0.048 (2)	0.002 (2)	0.000 (2)	−0.0055 (19)
C11	0.057 (2)	0.050 (2)	0.054 (2)	0.001 (2)	−0.011 (2)	−0.0116 (19)
C12	0.058 (2)	0.050 (2)	0.066 (2)	−0.012 (2)	−0.004 (2)	0.002 (2)
C13	0.057 (2)	0.050 (2)	0.049 (2)	−0.007 (2)	−0.0003 (19)	−0.0032 (18)
C14	0.0399 (19)	0.0430 (18)	0.0431 (18)	0.0008 (17)	−0.0055 (17)	0.0003 (15)

F1—C11	1.359 (4)	C4—C5	1.388 (4)
O1—C7	1.342 (4)	C4—H4A	0.9300
O1—C6	1.422 (4)	C5—C6	1.352 (5)
N1—C3	1.394 (4)	C5—H5A	0.9300
N1—H1A	0.8900	C7—C14	1.427 (4)
N1—H1B	0.8901	C8—H8A	0.9300
N2—C7	1.295 (4)	C9—C14	1.397 (5)
N2—C8	1.346 (4)	C9—C10	1.407 (5)
N3—C8	1.305 (5)	C10—C11	1.354 (5)
N3—C9	1.368 (4)	C10—H10A	0.9300
C1—C6	1.366 (5)	C11—C12	1.380 (5)
C1—C2	1.381 (5)	C12—C13	1.362 (5)
C1—H1C	0.9300	C12—H12A	0.9300
C2—C3	1.376 (5)	C13—C14	1.408 (4)
C2—H2B	0.9300	C13—H13A	0.9300
C3—C4	1.380 (5)
C7—O1—C6	117.6 (3)	N2—C7—O1	121.5 (3)
C3—N1—H1A	114.6	N2—C7—C14	123.4 (3)
C3—N1—H1B	117.1	O1—C7—C14	115.0 (3)
H1A—N1—H1B	109.0	N3—C8—N2	129.2 (4)
C7—N2—C8	115.3 (3)	N3—C8—H8A	115.4
C8—N3—C9	115.0 (3)	N2—C8—H8A	115.4
C6—C1—C2	119.1 (4)	N3—C9—C14	121.9 (3)
C6—C1—H1C	120.5	N3—C9—C10	118.5 (3)
C2—C1—H1C	120.5	C14—C9—C10	119.6 (3)
C3—C2—C1	121.3 (4)	C11—C10—C9	117.7 (3)
C3—C2—H2B	119.4	C11—C10—H10A	121.2
C1—C2—H2B	119.4	C9—C10—H10A	121.2
C2—C3—C4	118.1 (3)	C10—C11—F1	118.5 (4)
C2—C3—N1	122.2 (4)	C10—C11—C12	124.4 (3)
C4—C3—N1	119.7 (3)	F1—C11—C12	117.1 (3)
C3—C4—C5	120.8 (3)	C13—C12—C11	118.3 (3)
C3—C4—H4A	119.6	C13—C12—H12A	120.9
C5—C4—H4A	119.6	C11—C12—H12A	120.9
C6—C5—C4	119.5 (4)	C12—C13—C14	120.2 (3)
C6—C5—H5A	120.3	C12—C13—H13A	119.9
C4—C5—H5A	120.3	C14—C13—H13A	119.9
C5—C6—C1	121.2 (3)	C9—C14—C13	119.8 (3)
C5—C6—O1	119.6 (3)	C9—C14—C7	115.1 (3)
C1—C6—O1	119.1 (3)	C13—C14—C7	125.0 (3)
C6—C1—C2—C3	−0.6 (6)	C8—N3—C9—C10	−178.5 (4)
C1—C2—C3—C4	2.4 (5)	N3—C9—C10—C11	179.7 (3)
C1—C2—C3—N1	−175.6 (4)	C14—C9—C10—C11	0.7 (5)
C2—C3—C4—C5	−2.4 (5)	C9—C10—C11—F1	−179.8 (4)
N1—C3—C4—C5	175.6 (4)	C9—C10—C11—C12	0.4 (6)
C3—C4—C5—C6	0.6 (6)	C10—C11—C12—C13	−0.6 (6)
C4—C5—C6—C1	1.3 (5)	F1—C11—C12—C13	179.5 (4)
C4—C5—C6—O1	177.7 (3)	C11—C12—C13—C14	−0.2 (6)
C2—C1—C6—C5	−1.3 (5)	N3—C9—C14—C13	179.5 (3)
C2—C1—C6—O1	−177.7 (3)	C10—C9—C14—C13	−1.5 (5)
C7—O1—C6—C5	95.7 (4)	N3—C9—C14—C7	−1.2 (5)
C7—O1—C6—C1	−87.9 (4)	C10—C9—C14—C7	177.8 (3)
C8—N2—C7—O1	178.7 (3)	C12—C13—C14—C9	1.2 (5)
C8—N2—C7—C14	0.5 (5)	C12—C13—C14—C7	−178.0 (4)
C6—O1—C7—N2	−0.7 (5)	N2—C7—C14—C9	0.7 (5)
C6—O1—C7—C14	177.7 (3)	O1—C7—C14—C9	−177.7 (3)
C9—N3—C8—N2	0.8 (6)	N2—C7—C14—C13	179.9 (3)
C7—N2—C8—N3	−1.3 (6)	O1—C7—C14—C13	1.5 (5)
C8—N3—C9—C14	0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.89	2.67	3.408 (4)	142
N1—H1B···N3ii	0.89	2.38	3.205 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.89	2.67	3.408 (4)	142
N1—H1B⋯N3ii	0.89	2.38	3.205 (4)	154

Symmetry codes: (i) ; (ii) .