3-(2-Amino-ethyl)-2-(4-fluoroanilino)-quinazolin-4(3H)-one.

In the title mol-ecule, C(16)H(15)FN(4)O, the dihedral angle between the fluoro-substituted benzene ring and the pyrimidinone ring is 52.34 (7)°, while the dihedral angle between the fused benzene ring and the pyrimidinone ring is 3.30 (6)°. An intra-molecular N-H⋯N hydrogen bond may, in part, influence the conformation of the mol-ecule. In the crystal structure, inter-molecular N-H⋯N hydrogen bonds and weak C-H⋯π(arene) inter-actions link pairs of mol-ecules into centrosymmetric dimers.

Related literature

For the biological properties of quinazolinones and their derivatives, see: Armarego (1963 ▶); Witt & Bergman (2003 ▶). For details of our ongoing heterocyclic synthesis and drug discovery project, see: Yang et al. (2008 ▶).

Experimental

Crystal data

C16H15FN4O

M = 298.32

Triclinic,

a = 8.2836 (8) Å

b = 9.3103 (10) Å

c = 9.4952 (10) Å

α = 89.36 (1)°

β = 80.537 (10)°

γ = 77.163 (10)°

V = 704.03 (13) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 292 (2) K

0.20 × 0.10 × 0.10 mm

Data collection

Bruker SMART APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.970, T max = 0.990

4078 measured reflections

2726 independent reflections

2318 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.111

S = 1.05

2726 reflections

209 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.16 e Å−3

Δρmin = −0.15 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2003 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808035058/lh2717sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808035058/lh2717Isup2.hkl

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

C16H15FN4O	Z = 2
Mr = 298.32	F(000) = 312
Triclinic, P1	Dx = 1.407 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2836 (8) Å	Cell parameters from 2276 reflections
b = 9.3103 (10) Å	θ = 2.2–28.9°
c = 9.4952 (10) Å	µ = 0.10 mm−1
α = 89.36 (1)°	T = 292 K
β = 80.537 (10)°	Block, colourless
γ = 77.163 (10)°	0.20 × 0.10 × 0.10 mm
V = 704.03 (13) Å3

Bruker SMART APEX CCD diffractometer	2726 independent reflections
Radiation source: fine-focus sealed tube	2318 reflections with I > 2σ(I)
graphite	Rint = 0.012
ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→10
Tmin = 0.970, Tmax = 0.990	k = −11→11
4078 measured reflections	l = −11→11

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)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.1074P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.001
2726 reflections	Δρmax = 0.16 e Å−3
209 parameters	Δρmin = −0.15 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: 0.033 (5)

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
C1	0.26560 (18)	0.91647 (15)	0.45066 (18)	0.0596 (4)
C2	0.1522 (2)	0.87525 (15)	0.37986 (16)	0.0589 (4)
H2	0.1451	0.9031	0.2863	0.071*
C3	0.04783 (17)	0.79107 (14)	0.45047 (14)	0.0503 (3)
H3	−0.0308	0.7624	0.4040	0.060*
C4	0.05872 (15)	0.74874 (13)	0.58961 (14)	0.0449 (3)
C5	0.17665 (17)	0.79171 (15)	0.65820 (16)	0.0536 (3)
H5	0.1860	0.7632	0.7512	0.064*
C6	0.28049 (18)	0.87722 (16)	0.58782 (18)	0.0604 (4)
H6	0.3590	0.9074	0.6333	0.073*
C7	−0.02621 (15)	0.55612 (14)	0.74400 (13)	0.0424 (3)
C8	0.15458 (16)	0.37171 (14)	0.83809 (13)	0.0444 (3)
C9	0.31903 (18)	0.30166 (17)	0.85105 (16)	0.0573 (4)
H9	0.4075	0.3440	0.8121	0.069*
C10	0.3511 (2)	0.17169 (18)	0.92037 (17)	0.0670 (4)
H10	0.4613	0.1260	0.9272	0.080*
C11	0.2208 (2)	0.10669 (18)	0.98092 (18)	0.0690 (4)
H11	0.2438	0.0177	1.0271	0.083*
C12	0.0591 (2)	0.17479 (17)	0.97182 (16)	0.0587 (4)
H12	−0.0284	0.1326	1.0136	0.070*
C13	0.02374 (16)	0.30663 (14)	0.90063 (13)	0.0459 (3)
C14	−0.14830 (17)	0.37725 (15)	0.88772 (14)	0.0479 (3)
C15	−0.33989 (16)	0.58408 (16)	0.79762 (15)	0.0523 (3)
H15A	−0.3462	0.6893	0.8010	0.063*
H15B	−0.4153	0.5613	0.8799	0.063*
C16	−0.39955 (16)	0.54589 (16)	0.66308 (16)	0.0555 (4)
H16A	−0.3651	0.4403	0.6447	0.067*
H16B	−0.5212	0.5731	0.6772	0.067*
F1	0.36536 (13)	1.00298 (12)	0.38271 (13)	0.0901 (4)
N1	−0.06114 (14)	0.67357 (13)	0.65917 (13)	0.0496 (3)
H1	−0.151 (2)	0.6763 (17)	0.6150 (16)	0.060*
N2	0.12716 (13)	0.49763 (12)	0.75954 (11)	0.0459 (3)
H4A	−0.2947 (19)	0.5633 (17)	0.4621 (17)	0.055*
H4B	−0.411 (2)	0.6934 (17)	0.5178 (15)	0.055*
N3	−0.16619 (13)	0.50507 (12)	0.80814 (11)	0.0448 (3)
N4	−0.33145 (16)	0.62199 (16)	0.53930 (14)	0.0590 (3)
O1	−0.27139 (13)	0.33072 (12)	0.94041 (12)	0.0654 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0477 (8)	0.0456 (7)	0.0809 (10)	−0.0143 (6)	0.0073 (7)	0.0107 (7)
C2	0.0648 (9)	0.0473 (7)	0.0579 (8)	−0.0098 (7)	0.0053 (7)	0.0068 (6)
C3	0.0511 (8)	0.0419 (7)	0.0559 (8)	−0.0093 (6)	−0.0050 (6)	0.0015 (6)
C4	0.0364 (6)	0.0387 (6)	0.0566 (7)	−0.0069 (5)	−0.0015 (5)	0.0050 (5)
C5	0.0434 (7)	0.0536 (8)	0.0647 (8)	−0.0136 (6)	−0.0081 (6)	0.0092 (6)
C6	0.0413 (7)	0.0536 (8)	0.0880 (11)	−0.0148 (6)	−0.0097 (7)	0.0079 (7)
C7	0.0381 (7)	0.0470 (7)	0.0433 (6)	−0.0146 (5)	−0.0034 (5)	0.0022 (5)
C8	0.0434 (7)	0.0514 (7)	0.0409 (6)	−0.0159 (6)	−0.0071 (5)	0.0053 (5)
C9	0.0435 (8)	0.0697 (9)	0.0620 (8)	−0.0185 (7)	−0.0115 (6)	0.0179 (7)
C10	0.0518 (9)	0.0761 (10)	0.0731 (10)	−0.0097 (8)	−0.0183 (7)	0.0242 (8)
C11	0.0698 (10)	0.0655 (10)	0.0738 (10)	−0.0170 (8)	−0.0177 (8)	0.0287 (8)
C12	0.0584 (9)	0.0619 (9)	0.0592 (8)	−0.0235 (7)	−0.0063 (7)	0.0159 (7)
C13	0.0462 (7)	0.0517 (7)	0.0421 (6)	−0.0177 (6)	−0.0050 (5)	0.0039 (5)
C14	0.0447 (7)	0.0547 (7)	0.0460 (7)	−0.0201 (6)	−0.0007 (5)	0.0026 (6)
C15	0.0348 (7)	0.0582 (8)	0.0595 (8)	−0.0086 (6)	0.0028 (6)	0.0021 (6)
C16	0.0334 (7)	0.0580 (8)	0.0755 (9)	−0.0106 (6)	−0.0095 (6)	0.0043 (7)
F1	0.0763 (7)	0.0820 (7)	0.1149 (9)	−0.0407 (6)	0.0059 (6)	0.0289 (6)
N1	0.0379 (6)	0.0532 (7)	0.0607 (7)	−0.0154 (5)	−0.0099 (5)	0.0125 (5)
N2	0.0382 (6)	0.0514 (6)	0.0498 (6)	−0.0157 (5)	−0.0054 (4)	0.0094 (5)
N3	0.0353 (6)	0.0517 (6)	0.0476 (6)	−0.0142 (5)	−0.0013 (4)	0.0029 (5)
N4	0.0429 (7)	0.0710 (8)	0.0621 (8)	−0.0101 (6)	−0.0096 (6)	0.0019 (6)
O1	0.0476 (6)	0.0723 (7)	0.0788 (7)	−0.0275 (5)	0.0011 (5)	0.0166 (5)

C1—C2	1.362 (2)	C10—C11	1.392 (2)
C1—F1	1.3626 (16)	C10—H10	0.9300
C1—C6	1.366 (2)	C11—C12	1.365 (2)
C2—C3	1.3819 (19)	C11—H11	0.9300
C2—H2	0.9300	C12—C13	1.3914 (19)
C3—C4	1.3859 (19)	C12—H12	0.9300
C3—H3	0.9300	C13—C14	1.4551 (19)
C4—C5	1.388 (2)	C14—O1	1.2254 (15)
C4—N1	1.4123 (16)	C14—N3	1.3955 (17)
C5—C6	1.3870 (19)	C15—N3	1.4821 (16)
C5—H5	0.9300	C15—C16	1.516 (2)
C6—H6	0.9300	C15—H15A	0.9700
C7—N2	1.2980 (16)	C15—H15B	0.9700
C7—N1	1.3581 (17)	C16—N4	1.464 (2)
C7—N3	1.3956 (15)	C16—H16A	0.9700
C8—N2	1.3785 (16)	C16—H16B	0.9700
C8—C9	1.3981 (19)	N1—H1	0.908 (17)
C8—C13	1.4023 (18)	N4—H4A	0.889 (16)
C9—C10	1.366 (2)	N4—H4B	0.872 (16)
C9—H9	0.9300
C2—C1—F1	118.49 (14)	C10—C11—H11	120.3
C2—C1—C6	122.61 (13)	C11—C12—C13	120.67 (14)
F1—C1—C6	118.88 (15)	C11—C12—H12	119.7
C1—C2—C3	118.37 (14)	C13—C12—H12	119.7
C1—C2—H2	120.8	C12—C13—C8	120.13 (13)
C3—C2—H2	120.8	C12—C13—C14	120.69 (12)
C2—C3—C4	120.93 (13)	C8—C13—C14	119.18 (12)
C2—C3—H3	119.5	O1—C14—N3	120.70 (12)
C4—C3—H3	119.5	O1—C14—C13	124.22 (13)
C3—C4—C5	119.19 (12)	N3—C14—C13	115.08 (11)
C3—C4—N1	117.79 (12)	N3—C15—C16	113.90 (11)
C5—C4—N1	122.81 (12)	N3—C15—H15A	108.8
C6—C5—C4	119.92 (14)	C16—C15—H15A	108.8
C6—C5—H5	120.0	N3—C15—H15B	108.8
C4—C5—H5	120.0	C16—C15—H15B	108.8
C1—C6—C5	118.98 (14)	H15A—C15—H15B	107.7
C1—C6—H6	120.5	N4—C16—C15	111.68 (12)
C5—C6—H6	120.5	N4—C16—H16A	109.3
N2—C7—N1	120.96 (11)	C15—C16—H16A	109.3
N2—C7—N3	124.41 (11)	N4—C16—H16B	109.3
N1—C7—N3	114.62 (11)	C15—C16—H16B	109.3
N2—C8—C9	119.28 (12)	H16A—C16—H16B	107.9
N2—C8—C13	122.38 (12)	C7—N1—C4	124.69 (11)
C9—C8—C13	118.27 (12)	C7—N1—H1	114.5 (10)
C10—C9—C8	120.65 (14)	C4—N1—H1	115.2 (10)
C10—C9—H9	119.7	C7—N2—C8	117.77 (11)
C8—C9—H9	119.7	C14—N3—C7	121.02 (11)
C9—C10—C11	120.84 (14)	C14—N3—C15	116.82 (11)
C9—C10—H10	119.6	C7—N3—C15	122.16 (11)
C11—C10—H10	119.6	C16—N4—H4A	112.6 (10)
C12—C11—C10	119.42 (14)	C16—N4—H4B	109.1 (10)
C12—C11—H11	120.3	H4A—N4—H4B	106.8 (14)
F1—C1—C2—C3	−178.16 (12)	C8—C13—C14—O1	−178.72 (13)
C6—C1—C2—C3	0.4 (2)	C12—C13—C14—N3	−177.09 (12)
C1—C2—C3—C4	−0.4 (2)	C8—C13—C14—N3	1.78 (18)
C2—C3—C4—C5	−0.1 (2)	N3—C15—C16—N4	−78.30 (15)
C2—C3—C4—N1	174.74 (12)	N2—C7—N1—C4	−4.7 (2)
C3—C4—C5—C6	0.7 (2)	N3—C7—N1—C4	176.42 (11)
N1—C4—C5—C6	−173.93 (12)	C3—C4—N1—C7	138.77 (13)
C2—C1—C6—C5	0.2 (2)	C5—C4—N1—C7	−46.58 (19)
F1—C1—C6—C5	178.68 (12)	N1—C7—N2—C8	−174.97 (11)
C4—C5—C6—C1	−0.7 (2)	N3—C7—N2—C8	3.84 (19)
N2—C8—C9—C10	−175.78 (14)	C9—C8—N2—C7	176.85 (12)
C13—C8—C9—C10	1.3 (2)	C13—C8—N2—C7	−0.13 (19)
C8—C9—C10—C11	−0.6 (3)	O1—C14—N3—C7	−177.93 (12)
C9—C10—C11—C12	−0.6 (3)	C13—C14—N3—C7	1.58 (17)
C10—C11—C12—C13	1.2 (3)	O1—C14—N3—C15	3.07 (19)
C11—C12—C13—C8	−0.5 (2)	C13—C14—N3—C15	−177.42 (11)
C11—C12—C13—C14	178.40 (13)	N2—C7—N3—C14	−4.69 (19)
N2—C8—C13—C12	176.23 (12)	N1—C7—N3—C14	174.18 (11)
C9—C8—C13—C12	−0.8 (2)	N2—C7—N3—C15	174.25 (12)
N2—C8—C13—C14	−2.65 (19)	N1—C7—N3—C15	−6.87 (17)
C9—C8—C13—C14	−179.65 (12)	C16—C15—N3—C14	−96.27 (14)
C12—C13—C14—O1	2.4 (2)	C16—C15—N3—C7	84.75 (15)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N4	0.908 (17)	1.925 (17)	2.8049 (17)	162.8 (14)
N4—H4A···N2i	0.889 (16)	2.323 (16)	3.1321 (18)	151.4 (13)
C3—H3···Cgi	0.93	2.77 (1)	3.4741 (15)	132 (1)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N4	0.908 (17)	1.925 (17)	2.8049 (17)	162.8 (14)
N4—H4A⋯N2i	0.889 (16)	2.323 (16)	3.1321 (18)	151.4 (13)
C3—H3⋯Cgi	0.93	2.77 (1)	3.4741 (15)	132 (1)

Symmetry code: (i) . Cg is the centroid of atoms N2/C7/N3/C14/C13/C8.