3-(2-Amino-eth-yl)-2-[4-(trifluoro-meth-oxy)anilino]quinazolin-4(3H)-one.

In the title compound, C(17)H(15)F(3)N(4)O(2), the dihedral angle between the trifluoro-meth-oxy-substituted benzene ring and the pyrimidinone ring is 45.1 (5)°, while that between the fused benzene ring and the pyrimidinone ring is 0.67 (1)°. Part of one of the benzene rings and its trifluoro-meth-oxy substituent are disordered over two positions of approximately equal occupancy (0.51:0.49). Inter-molecular N-H⋯O and N-H⋯N hydrogen bonds contribute to the stability of the crystal structure. A weak intra-molecular C-H⋯F contact is also found. In addition, π-π stacking inter-actions, with centroid-centroid distances in the range 3.673 (6)-3.780 (8) Å, and weak C-H⋯π inter-actions are also observed.

Related literature

For the biological activity of quinazoline-4(3H)-one derivatives, see: Pandeya et al.(1999 ▶); Shiba et al. (1997 ▶), Malamas & Millen (1991 ▶); Mannschreck et al. (1984 ▶); Kung et al. (1999 ▶); Bartroli et al. (1998 ▶); Palmer et al. (1997 ▶); Tsou et al. (2001 ▶); Matsuno et al. (2002 ▶). For the synthesis of the title compound, see: Yang et al. (2008 ▶).

Experimental

Crystal data

C17H15F3N4O2

M = 364.33

Orthorhombic,

a = 11.9675 (13) Å

b = 12.9579 (13) Å

c = 21.280 (2) Å

V = 3300.0 (6) Å3

Z = 8

Mo Kα radiation

μ = 0.12 mm−1

T = 298 K

0.23 × 0.15 × 0.11 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ▶) T min = 0.973, T max = 0.987

15599 measured reflections

3076 independent reflections

2573 reflections with I > 2σ(I)

R int = 0.083

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.164

S = 1.12

3076 reflections

311 parameters

19 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.39 e Å−3

Δρmin = −0.29 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810024645/sj5026sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810024645/sj5026Isup2.hkl

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

C17H15F3N4O2	F(000) = 1504
Mr = 364.33	Dx = 1.467 Mg m−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 4600 reflections
a = 11.9675 (13) Å	θ = 2.5–23.5°
b = 12.9579 (13) Å	µ = 0.12 mm−1
c = 21.280 (2) Å	T = 298 K
V = 3300.0 (6) Å3	Block, colorless
Z = 8	0.23 × 0.15 × 0.11 mm

Bruker SMART APEX CCD area-detector diffractometer	3076 independent reflections
Radiation source: fine-focus sealed tube	2573 reflections with I > 2σ(I)
graphite	Rint = 0.083
φ and ω scans	θmax = 25.5°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −10→14
Tmin = 0.973, Tmax = 0.987	k = −15→14
15599 measured reflections	l = −25→25

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.164	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0809P)2 + 0.8235P] where P = (Fo2 + 2Fc2)/3
3076 reflections	(Δ/σ)max < 0.001
311 parameters	Δρmax = 0.39 e Å−3
19 restraints	Δρmin = −0.29 e Å−3

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	Occ. (<1)
C1	0.9187 (2)	1.31297 (18)	0.55231 (11)	0.0445 (6)
C2	0.9408 (2)	1.24194 (18)	0.60015 (11)	0.0443 (6)
C3	0.9930 (2)	1.2767 (2)	0.65508 (12)	0.0556 (7)
H3	1.0093	1.2304	0.6871	0.067*
C4	1.0200 (2)	1.3792 (2)	0.66172 (14)	0.0623 (7)
H4	1.0546	1.4014	0.6984	0.075*
C5	0.9967 (2)	1.4498 (2)	0.61481 (14)	0.0631 (8)
H5	1.0156	1.5189	0.6199	0.076*
C6	0.9457 (2)	1.41721 (19)	0.56101 (14)	0.0549 (7)
H6	0.9286	1.4648	0.5297	0.066*
C7	0.8649 (2)	1.27789 (18)	0.49482 (11)	0.0453 (6)
C8	0.8673 (2)	1.10775 (18)	0.54329 (10)	0.0425 (6)
C9	0.7649 (2)	1.1385 (2)	0.44173 (12)	0.0522 (6)
H9A	0.7257	1.1979	0.4249	0.063*
H9B	0.7092	1.0915	0.4585	0.063*
C10	0.8258 (2)	1.0850 (2)	0.38838 (11)	0.0555 (7)
H10A	0.7795	1.0861	0.3510	0.067*
H10B	0.8943	1.1220	0.3791	0.067*
C11	0.8519 (2)	0.92710 (18)	0.57795 (12)	0.0463 (6)
C12	0.8785 (2)	0.82950 (18)	0.55666 (12)	0.0463 (6)
H12	0.8970	0.8200	0.5146	0.056*
C13	0.8781 (2)	0.74562 (19)	0.59680 (13)	0.0523 (7)
H13	0.8987	0.6808	0.5821	0.063*
C14	0.8473 (13)	0.7581 (8)	0.6583 (5)	0.065 (5)	0.51
C15	0.812 (2)	0.855 (2)	0.6764 (13)	0.071 (6)	0.51
H15	0.7805	0.8616	0.7161	0.085*	0.51
C16	0.8208 (17)	0.9417 (9)	0.6397 (8)	0.050 (3)	0.51
H16	0.8065	1.0072	0.6558	0.060*	0.51
C17	0.8238 (9)	0.6670 (8)	0.7538 (5)	0.0637 (12)	0.51
O2	0.8387 (12)	0.6644 (9)	0.6922 (5)	0.089 (4)	0.51
F1	0.8935 (8)	0.7216 (9)	0.7869 (6)	0.119 (4)	0.51
F2	0.7234 (6)	0.7043 (7)	0.7658 (5)	0.122 (4)	0.51
F3	0.8159 (10)	0.5681 (5)	0.7691 (4)	0.082 (2)	0.51
C14'	0.8582 (12)	0.7631 (9)	0.6591 (6)	0.063 (5)	0.49
C15'	0.842 (3)	0.8590 (19)	0.6855 (14)	0.071 (6)	0.49
H15'	0.8374	0.8700	0.7286	0.085*	0.49
C16'	0.834 (3)	0.9368 (16)	0.6418 (13)	0.101 (8)	0.49
H16'	0.8148	1.0020	0.6566	0.121*	0.49
C17'	0.8114 (10)	0.6564 (9)	0.7475 (6)	0.0637 (12)	0.49
O2'	0.8747 (11)	0.6749 (8)	0.6976 (5)	0.070 (3)	0.49
F1'	0.8435 (10)	0.7198 (6)	0.7928 (4)	0.105 (4)	0.49
F2'	0.7057 (9)	0.6717 (8)	0.7373 (5)	0.122 (4)	0.49
F3'	0.8383 (15)	0.5654 (9)	0.7708 (7)	0.145 (6)	0.49
N1	0.83729 (16)	1.17338 (14)	0.49385 (9)	0.0428 (5)
N2	0.91631 (18)	1.13823 (14)	0.59417 (9)	0.0469 (5)
N3	0.8525 (2)	0.97796 (19)	0.40455 (11)	0.0605 (6)
H3A	0.7992 (19)	0.936 (2)	0.3949 (14)	0.073*
H3B	0.9115 (17)	0.952 (2)	0.3871 (14)	0.073*
N4	0.8435 (2)	1.00667 (16)	0.53333 (9)	0.0510 (6)
H4A	0.843 (2)	0.988 (2)	0.4945 (6)	0.061*
O1	0.84285 (17)	1.33377 (14)	0.45034 (9)	0.0620 (6)

	U11	U22	U33	U12	U13	U23
C1	0.0419 (13)	0.0403 (12)	0.0513 (13)	0.0033 (10)	0.0089 (11)	0.0027 (10)
C2	0.0470 (13)	0.0410 (13)	0.0449 (13)	−0.0008 (10)	0.0068 (10)	0.0003 (10)
C3	0.0640 (17)	0.0577 (16)	0.0452 (13)	−0.0084 (13)	0.0010 (12)	−0.0015 (11)
C4	0.0643 (18)	0.0622 (18)	0.0604 (16)	−0.0108 (14)	0.0069 (14)	−0.0154 (14)
C5	0.0644 (18)	0.0428 (14)	0.082 (2)	−0.0098 (12)	0.0113 (16)	−0.0141 (13)
C6	0.0550 (15)	0.0397 (13)	0.0702 (17)	0.0013 (11)	0.0113 (13)	0.0066 (12)
C7	0.0455 (13)	0.0415 (13)	0.0490 (13)	0.0078 (10)	0.0076 (11)	0.0077 (10)
C8	0.0465 (13)	0.0402 (12)	0.0410 (12)	0.0001 (10)	0.0031 (10)	0.0038 (10)
C9	0.0521 (15)	0.0527 (15)	0.0519 (13)	0.0026 (11)	−0.0113 (12)	0.0054 (11)
C10	0.0634 (16)	0.0601 (16)	0.0431 (13)	−0.0049 (13)	−0.0077 (12)	0.0038 (12)
C11	0.0535 (14)	0.0399 (13)	0.0455 (13)	−0.0049 (10)	−0.0006 (11)	0.0033 (10)
C12	0.0491 (14)	0.0431 (13)	0.0466 (13)	−0.0014 (10)	−0.0007 (11)	−0.0015 (10)
C13	0.0601 (16)	0.0386 (13)	0.0583 (16)	0.0076 (11)	−0.0039 (13)	−0.0029 (11)
C14	0.121 (10)	0.032 (7)	0.043 (7)	−0.017 (6)	−0.026 (6)	−0.002 (4)
C15	0.118 (13)	0.063 (7)	0.033 (7)	−0.014 (7)	0.003 (6)	−0.004 (4)
C16	0.097 (7)	0.014 (4)	0.040 (6)	−0.001 (4)	0.011 (5)	0.001 (4)
C17	0.084 (3)	0.054 (2)	0.053 (2)	0.002 (2)	−0.004 (2)	0.0146 (19)
O2	0.167 (12)	0.046 (3)	0.055 (3)	−0.033 (5)	−0.014 (5)	0.013 (2)
F1	0.111 (6)	0.144 (6)	0.101 (6)	0.025 (4)	−0.036 (4)	−0.008 (4)
F2	0.084 (5)	0.107 (6)	0.177 (9)	0.021 (4)	0.060 (6)	0.059 (6)
F3	0.132 (5)	0.045 (3)	0.070 (4)	0.001 (3)	0.018 (3)	0.038 (3)
C14'	0.071 (6)	0.050 (9)	0.069 (9)	0.024 (5)	0.032 (6)	0.027 (6)
C15'	0.139 (17)	0.036 (6)	0.037 (8)	0.003 (8)	0.006 (9)	0.006 (5)
C16'	0.164 (19)	0.075 (11)	0.064 (12)	0.026 (9)	0.035 (11)	0.001 (8)
C17'	0.084 (3)	0.054 (2)	0.053 (2)	0.002 (2)	−0.004 (2)	0.0146 (19)
O2'	0.098 (6)	0.038 (4)	0.076 (5)	0.016 (4)	0.022 (5)	0.011 (3)
F1'	0.197 (12)	0.074 (4)	0.045 (3)	0.000 (5)	−0.031 (5)	−0.014 (2)
F2'	0.107 (5)	0.116 (7)	0.144 (7)	−0.005 (4)	−0.023 (5)	0.038 (5)
F3'	0.186 (11)	0.112 (8)	0.137 (9)	0.059 (6)	−0.005 (7)	0.054 (6)
N1	0.0465 (11)	0.0404 (11)	0.0416 (10)	0.0029 (8)	−0.0018 (8)	0.0038 (8)
N2	0.0591 (13)	0.0395 (11)	0.0421 (11)	−0.0024 (9)	−0.0030 (9)	0.0057 (8)
N3	0.0730 (17)	0.0565 (15)	0.0518 (13)	0.0004 (12)	−0.0036 (12)	−0.0049 (11)
N4	0.0754 (15)	0.0385 (11)	0.0389 (11)	−0.0060 (10)	−0.0015 (10)	0.0022 (9)
O1	0.0760 (13)	0.0527 (11)	0.0573 (11)	0.0087 (9)	−0.0023 (9)	0.0205 (9)

C1—C2	1.398 (3)	C11—N4	1.405 (3)
C1—C6	1.401 (3)	C12—C13	1.382 (3)
C1—C7	1.455 (4)	C12—H12	0.9300
C2—N2	1.381 (3)	C13—C14'	1.366 (14)
C2—C3	1.399 (3)	C13—C14	1.369 (13)
C3—C4	1.374 (4)	C13—H13	0.9300
C3—H3	0.9300	C14—C15	1.38 (3)
C4—C5	1.382 (4)	C14—O2	1.416 (9)
C4—H4	0.9300	C15—C16	1.38 (4)
C5—C6	1.364 (4)	C15—H15	0.9300
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—F1	1.302 (9)
C7—O1	1.221 (3)	C17—F2	1.321 (9)
C7—N1	1.394 (3)	C17—O2	1.324 (9)
C8—N2	1.293 (3)	C17—F3	1.326 (8)
C8—N4	1.357 (3)	C14'—C15'	1.38 (3)
C8—N1	1.400 (3)	C14'—O2'	1.421 (8)
C9—N1	1.478 (3)	C15'—C16'	1.37 (4)
C9—C10	1.517 (4)	C15'—H15'	0.9300
C9—H9A	0.9700	C16'—H16'	0.9300
C9—H9B	0.9700	C17'—F2'	1.299 (9)
C10—N3	1.464 (4)	C17'—F3'	1.320 (9)
C10—H10A	0.9700	C17'—F1'	1.325 (9)
C10—H10B	0.9700	C17'—O2'	1.325 (9)
C11—C16	1.379 (18)	N3—H3A	0.862 (11)
C11—C12	1.381 (3)	N3—H3B	0.864 (11)
C11—C16'	1.38 (3)	N4—H4A	0.863 (11)
C2—C1—C6	119.7 (2)	C14—C13—C12	119.9 (5)
C2—C1—C7	119.4 (2)	C14'—C13—H13	121.6
C6—C1—C7	120.9 (2)	C14—C13—H13	120.1
N2—C2—C1	122.2 (2)	C12—C13—H13	120.1
N2—C2—C3	119.0 (2)	C13—C14—C15	117.3 (15)
C1—C2—C3	118.7 (2)	C13—C14—O2	113.9 (9)
C4—C3—C2	120.1 (3)	C15—C14—O2	127.9 (17)
C4—C3—H3	119.9	C14—C15—C16	124 (2)
C2—C3—H3	119.9	C14—C15—H15	117.9
C3—C4—C5	121.2 (3)	C16—C15—H15	117.9
C3—C4—H4	119.4	C15—C16—C11	116.7 (16)
C5—C4—H4	119.4	C15—C16—H16	121.7
C6—C5—C4	119.4 (2)	C11—C16—H16	121.7
C6—C5—H5	120.3	F1—C17—F2	106.2 (9)
C4—C5—H5	120.3	F1—C17—O2	117.7 (11)
C5—C6—C1	120.8 (3)	F2—C17—O2	108.9 (11)
C5—C6—H6	119.6	F1—C17—F3	116.0 (10)
C1—C6—H6	119.6	F2—C17—F3	104.0 (9)
O1—C7—N1	120.9 (2)	O2—C17—F3	103.2 (9)
O1—C7—C1	124.2 (2)	C17—O2—C14	119.5 (11)
N1—C7—C1	114.88 (19)	C13—C14'—C15'	124.8 (15)
N2—C8—N4	121.4 (2)	C13—C14'—O2'	113.7 (10)
N2—C8—N1	124.1 (2)	C15'—C14'—O2'	120.6 (16)
N4—C8—N1	114.5 (2)	C16'—C15'—C14'	113 (2)
N1—C9—C10	114.8 (2)	C16'—C15'—H15'	123.3
N1—C9—H9A	108.6	C14'—C15'—H15'	123.3
C10—C9—H9A	108.6	C15'—C16'—C11	126 (2)
N1—C9—H9B	108.6	C15'—C16'—H16'	117.0
C10—C9—H9B	108.6	C11—C16'—H16'	117.0
H9A—C9—H9B	107.5	F2'—C17'—F3'	115.9 (11)
N3—C10—C9	111.2 (2)	F2'—C17'—F1'	108.1 (9)
N3—C10—H10A	109.4	F3'—C17'—F1'	102.1 (10)
C9—C10—H10A	109.4	F2'—C17'—O2'	113.3 (11)
N3—C10—H10B	109.4	F3'—C17'—O2'	108.8 (11)
C9—C10—H10B	109.4	F1'—C17'—O2'	107.8 (10)
H10A—C10—H10B	108.0	C17'—O2'—C14'	121.8 (11)
C16—C11—C12	120.0 (6)	C7—N1—C8	121.2 (2)
C16—C11—C16'	7(2)	C7—N1—C9	116.56 (19)
C12—C11—C16'	116.2 (10)	C8—N1—C9	121.9 (2)
C16—C11—N4	121.6 (6)	C8—N2—C2	118.07 (19)
C12—C11—N4	117.8 (2)	C10—N3—H3A	112 (2)
C16'—C11—N4	125.9 (10)	C10—N3—H3B	116 (2)
C11—C12—C13	121.1 (2)	H3A—N3—H3B	105 (3)
C11—C12—H12	119.4	C8—N4—C11	126.0 (2)
C13—C12—H12	119.4	C8—N4—H4A	115.3 (19)
C14'—C13—C14	6.1 (12)	C11—N4—H4A	115.9 (19)
C14'—C13—C12	118.0 (5)
C6—C1—C2—N2	−179.8 (2)	C15—C14—O2—C17	−20 (2)
C7—C1—C2—N2	1.9 (3)	C14—C13—C14'—C15'	−112 (10)
C6—C1—C2—C3	−2.0 (3)	C12—C13—C14'—C15'	−2(2)
C7—C1—C2—C3	179.8 (2)	C14—C13—C14'—O2'	79 (9)
N2—C2—C3—C4	178.9 (2)	C12—C13—C14'—O2'	−171.7 (9)
C1—C2—C3—C4	1.0 (4)	C13—C14'—C15'—C16'	8(3)
C2—C3—C4—C5	0.0 (4)	O2'—C14'—C15'—C16'	176 (2)
C3—C4—C5—C6	0.2 (4)	C14'—C15'—C16'—C11	−7(4)
C4—C5—C6—C1	−1.2 (4)	C16—C11—C16'—C15'	124 (12)
C2—C1—C6—C5	2.2 (4)	C12—C11—C16'—C15'	1(3)
C7—C1—C6—C5	−179.6 (2)	N4—C11—C16'—C15'	180 (2)
C2—C1—C7—O1	−179.5 (2)	F2'—C17'—O2'—C14'	43.8 (16)
C6—C1—C7—O1	2.3 (4)	F3'—C17'—O2'—C14'	174.2 (14)
C2—C1—C7—N1	1.6 (3)	F1'—C17'—O2'—C14'	−75.8 (15)
C6—C1—C7—N1	−176.6 (2)	C13—C14'—O2'—C17'	−144.6 (11)
N1—C9—C10—N3	78.7 (3)	C15'—C14'—O2'—C17'	45 (2)
C16—C11—C12—C13	−2.0 (10)	O1—C7—N1—C8	176.8 (2)
C16'—C11—C12—C13	5.1 (15)	C1—C7—N1—C8	−4.3 (3)
N4—C11—C12—C13	−173.9 (2)	O1—C7—N1—C9	−9.6 (3)
C11—C12—C13—C14'	−4.5 (8)	C1—C7—N1—C9	169.3 (2)
C11—C12—C13—C14	2.2 (8)	N2—C8—N1—C7	3.8 (4)
C14'—C13—C14—C15	77 (9)	N4—C8—N1—C7	−174.5 (2)
C12—C13—C14—C15	3.3 (19)	N2—C8—N1—C9	−169.5 (2)
C14'—C13—C14—O2	−113 (9)	N4—C8—N1—C9	12.2 (3)
C12—C13—C14—O2	173.4 (8)	C10—C9—N1—C7	100.9 (3)
C13—C14—C15—C16	−10 (3)	C10—C9—N1—C8	−85.5 (3)
O2—C14—C15—C16	−178.0 (19)	N4—C8—N2—C2	178.1 (2)
C14—C15—C16—C11	10 (3)	N1—C8—N2—C2	−0.1 (4)
C12—C11—C16—C15	−4(2)	C1—C2—N2—C8	−2.7 (3)
C16'—C11—C16—C15	−64 (10)	C3—C2—N2—C8	179.4 (2)
N4—C11—C16—C15	168.0 (16)	N2—C8—N4—C11	10.1 (4)
F1—C17—O2—C14	−52.8 (17)	N1—C8—N4—C11	−171.5 (2)
F2—C17—O2—C14	68.0 (15)	C16—C11—N4—C8	39.3 (10)
F3—C17—O2—C14	178.0 (13)	C12—C11—N4—C8	−148.9 (2)
C13—C14—O2—C17	171.3 (11)	C16'—C11—N4—C8	32.2 (16)

Cg1 is the centroid of the N1/C7/C1/C2/N2/C8 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3B···N2i	0.86 (1)	2.40 (2)	3.150 (3)	145 (3)
N3—H3A···O1ii	0.86 (1)	2.46 (2)	3.147 (3)	137 (3)
C15—H15···F2	0.93	2.40	2.93 (3)	116
C12—H12···Cg1i	0.93	2.88	3.560 (3)	131

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the N1/C7/C1/C2/N2/C8 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3B⋯N2i	0.86 (1)	2.40 (2)	3.150 (3)	145 (3)
N3—H3A⋯O1ii	0.86 (1)	2.46 (2)	3.147 (3)	137 (3)
C15—H15⋯F2	0.93	2.40	2.93 (3)	116
C12—H12⋯Cg1i	0.93	2.88	3.560 (3)	131

Symmetry codes: (i) ; (ii) .