2-(4-Fluoro-anilino)-3-(2-hydroxy-ethyl)quinazolin-4(3H)-one.

The mol-ecular and crystal structures of the title compound, C(16)H(14)FN(3)O(2), are stabilized by intra-molecular N-H⋯O and inter-molecular O-H⋯O hydrogen bonds. The existence of non-classical intra-molecular C-H⋯N hydrogen bonds provides a dihedral angle between the fluoro-substituted benzene and pyrimidinone rings of 7.9 (1)°.

Related literature

For the pharmacological activity of N3 and C7 disubstituted quinazolines, see: Usha et al. (2006 ▶). For the synthesis of quinazolinone and thienopyrimidinones, see: Yang et al. (2008 ▶). For synthesis, drug discovery and crystal structures, see: Yang & Wu (2008 ▶); Wang et al. (2008 ▶).

Experimental

Crystal data

C16H14FN3O2

M = 299.30

Monoclinic,

a = 8.5737 (8) Å

b = 10.8268 (10) Å

c = 15.2490 (13) Å

β = 104.070(10)°

V = 1371.0 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.11 mm−1

T = 273 K

0.10 × 0.10 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: none

8342 measured reflections

2976 independent reflections

2475 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.102

S = 1.06

2976 reflections

205 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.13 e Å−3

Δρmin = −0.24 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: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809006254/rk2120sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809006254/rk2120Isup2.hkl

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

C16H14FN3O2	F(000) = 624
Mr = 299.30	Dx = 1.450 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3320 reflections
a = 8.5737 (8) Å	θ = 2.3–29.2°
b = 10.8268 (10) Å	µ = 0.11 mm−1
c = 15.2490 (13) Å	T = 273 K
β = 104.407 (1)°	Block, colourless
V = 1371.0 (2) Å3	0.10 × 0.10 × 0.10 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	2475 reflections with I > 2σ(I)
Radiation source: Fine–focus sealed tube	Rint = 0.021
Graphite	θmax = 27.0°, θmin = 2.3°
φ and ω scans	h = −10→10
8342 measured reflections	k = −12→13
2976 independent reflections	l = −19→14

Refinement on F2	Primary atom site location: Direct
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F2 > 2σ(F2)] = 0.037	Hydrogen site location: Geom
wR(F2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0546P)2 + 0.157P] where P = (Fo2 + 2Fc2)/3
2976 reflections	(Δ/σ)max = 0.001
205 parameters	Δρmax = 0.13 e Å−3
2 restraints	Δρmin = −0.23 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.56770 (14)	0.34529 (11)	−0.09177 (9)	0.0442 (3)
C2	0.59291 (15)	0.34162 (11)	0.00070 (9)	0.0455 (3)
H2	0.5444	0.2813	0.0283	0.055*
C3	0.69136 (15)	0.42908 (11)	0.05135 (8)	0.0427 (3)
H3	0.7096	0.4276	0.1141	0.051*
C4	0.76459 (13)	0.52003 (10)	0.01077 (8)	0.0379 (3)
C5	0.73709 (15)	0.52084 (12)	−0.08302 (8)	0.0438 (3)
H5	0.7852	0.5807	−0.1113	0.053*
C6	0.63794 (15)	0.43247 (12)	−0.13419 (8)	0.0458 (3)
H6	0.6193	0.4325	−0.1969	0.055*
C7	0.94732 (13)	0.70237 (10)	0.05017 (7)	0.0377 (3)
C8	1.13407 (14)	0.86392 (11)	0.11798 (8)	0.0418 (3)
C9	1.15360 (14)	0.88561 (11)	0.02741 (8)	0.0402 (3)
C10	1.06202 (13)	0.81559 (11)	−0.04382 (8)	0.0389 (3)
C11	1.08192 (15)	0.83508 (12)	−0.13148 (8)	0.0462 (3)
H11	1.0220	0.7892	−0.1798	0.055*
C12	1.18945 (16)	0.92159 (13)	−0.14591 (9)	0.0520 (3)
H12	1.2025	0.9334	−0.2041	0.062*
C13	1.27943 (17)	0.99209 (13)	−0.07485 (10)	0.0549 (3)
H13	1.3514	1.0510	−0.0857	0.066*
C14	1.26168 (16)	0.97446 (12)	0.01099 (10)	0.0504 (3)
H14	1.3215	1.0216	0.0586	0.060*
C15	0.97517 (16)	0.76912 (12)	0.21207 (8)	0.0450 (3)
H15A	0.8617	0.7484	0.1999	0.054*
H15B	0.9889	0.8505	0.2395	0.054*
C16	1.06872 (18)	0.67775 (13)	0.27916 (8)	0.0526 (3)
H16A	1.1828	0.6861	0.2827	0.063*
H16B	1.0521	0.6944	0.3387	0.063*
F1	0.46983 (11)	0.25850 (8)	−0.14287 (6)	0.0651 (3)
N1	0.85952 (13)	0.60633 (10)	0.07009 (7)	0.0439 (2)
H1	0.8863 (16)	0.5818 (12)	0.1269 (6)	0.053*
N2	1.02153 (12)	0.77481 (9)	0.12481 (6)	0.0393 (2)
N3	0.96041 (12)	0.72240 (9)	−0.03130 (6)	0.0411 (2)
O1	1.20713 (12)	0.91951 (9)	0.18653 (6)	0.0565 (3)
O2	1.01772 (12)	0.55593 (9)	0.25230 (6)	0.0546 (3)
H2A	1.0973 (16)	0.5093 (14)	0.2698 (12)	0.082*

	U11	U22	U33	U12	U13	U23
C1	0.0436 (6)	0.0404 (6)	0.0481 (7)	−0.0004 (5)	0.0105 (5)	−0.0022 (5)
C2	0.0492 (7)	0.0396 (6)	0.0504 (7)	0.0018 (5)	0.0174 (6)	0.0082 (5)
C3	0.0499 (7)	0.0442 (6)	0.0356 (6)	0.0072 (5)	0.0135 (5)	0.0067 (5)
C4	0.0379 (6)	0.0404 (6)	0.0360 (6)	0.0046 (5)	0.0104 (5)	0.0012 (5)
C5	0.0492 (7)	0.0480 (7)	0.0357 (6)	−0.0038 (5)	0.0132 (5)	0.0024 (5)
C6	0.0508 (7)	0.0519 (7)	0.0352 (6)	−0.0028 (6)	0.0114 (5)	−0.0017 (5)
C7	0.0370 (6)	0.0411 (6)	0.0333 (6)	0.0052 (5)	0.0058 (4)	0.0015 (5)
C8	0.0416 (6)	0.0426 (6)	0.0409 (6)	0.0040 (5)	0.0094 (5)	−0.0044 (5)
C9	0.0388 (6)	0.0399 (6)	0.0420 (6)	0.0059 (5)	0.0102 (5)	0.0020 (5)
C10	0.0377 (6)	0.0406 (6)	0.0376 (6)	0.0065 (5)	0.0080 (5)	0.0053 (5)
C11	0.0476 (7)	0.0538 (7)	0.0351 (6)	0.0046 (6)	0.0060 (5)	0.0081 (5)
C12	0.0531 (7)	0.0602 (8)	0.0442 (7)	0.0058 (6)	0.0149 (6)	0.0147 (6)
C13	0.0513 (8)	0.0542 (8)	0.0607 (9)	−0.0035 (6)	0.0168 (6)	0.0112 (7)
C14	0.0489 (7)	0.0483 (7)	0.0536 (8)	−0.0022 (6)	0.0121 (6)	−0.0010 (6)
C15	0.0535 (7)	0.0494 (7)	0.0348 (6)	0.0053 (6)	0.0160 (5)	−0.0031 (5)
C16	0.0621 (8)	0.0616 (8)	0.0327 (6)	0.0034 (6)	0.0092 (6)	−0.0009 (6)
F1	0.0736 (6)	0.0599 (5)	0.0592 (5)	−0.0229 (4)	0.0116 (4)	−0.0068 (4)
N1	0.0521 (6)	0.0494 (6)	0.0297 (5)	−0.0036 (5)	0.0092 (4)	0.0026 (4)
N2	0.0434 (5)	0.0436 (5)	0.0316 (5)	0.0037 (4)	0.0104 (4)	−0.0013 (4)
N3	0.0436 (5)	0.0456 (6)	0.0331 (5)	0.0000 (4)	0.0077 (4)	0.0028 (4)
O1	0.0601 (6)	0.0639 (6)	0.0450 (5)	−0.0115 (5)	0.0123 (4)	−0.0152 (4)
O2	0.0629 (6)	0.0552 (6)	0.0421 (5)	0.0091 (4)	0.0062 (4)	0.0055 (4)

C1—C6	1.3659 (17)	C9—C14	1.4007 (17)
C1—F1	1.3670 (14)	C10—N3	1.3771 (15)
C1—C2	1.3729 (18)	C10—C11	1.4050 (16)
C2—C3	1.3716 (18)	C11—C12	1.3699 (19)
C2—H2	0.9300	C11—H11	0.9300
C3—C4	1.3929 (16)	C12—C13	1.391 (2)
C3—H3	0.9300	C12—H12	0.9300
C4—C5	1.3904 (16)	C13—C14	1.3683 (19)
C4—N1	1.4098 (15)	C13—H13	0.9300
C5—C6	1.3846 (17)	C14—H14	0.9300
C5—H5	0.9300	C15—N2	1.4817 (14)
C6—H6	0.9300	C15—C16	1.5035 (18)
C7—N3	1.2932 (14)	C15—H15A	0.9700
C7—N1	1.3616 (15)	C15—H15B	0.9700
C7—N2	1.3983 (15)	C16—O2	1.4174 (17)
C8—O1	1.2335 (14)	C16—H16A	0.9700
C8—N2	1.3866 (15)	C16—H16B	0.9700
C8—C9	1.4511 (16)	N1—H1	0.881 (9)
C9—C10	1.3952 (16)	O2—H2A	0.837 (9)
C6—C1—F1	119.04 (11)	C12—C11—H11	120.0
C6—C1—C2	122.08 (12)	C10—C11—H11	120.0
F1—C1—C2	118.88 (11)	C11—C12—C13	120.99 (12)
C3—C2—C1	118.42 (11)	C11—C12—H12	119.5
C3—C2—H2	120.8	C13—C12—H12	119.5
C1—C2—H2	120.8	C14—C13—C12	119.76 (12)
C2—C3—C4	121.34 (11)	C14—C13—H13	120.1
C2—C3—H3	119.3	C12—C13—H13	120.1
C4—C3—H3	119.3	C13—C14—C9	120.19 (13)
C5—C4—C3	118.79 (11)	C13—C14—H14	119.9
C5—C4—N1	125.37 (11)	C9—C14—H14	119.9
C3—C4—N1	115.82 (10)	N2—C15—C16	114.93 (10)
C6—C5—C4	119.90 (11)	N2—C15—H15A	108.5
C6—C5—H5	120.0	C16—C15—H15A	108.5
C4—C5—H5	120.0	N2—C15—H15B	108.5
C1—C6—C5	119.46 (11)	C16—C15—H15B	108.5
C1—C6—H6	120.3	H15A—C15—H15B	107.5
C5—C6—H6	120.3	O2—C16—C15	109.98 (11)
N3—C7—N1	121.83 (11)	O2—C16—H16A	109.7
N3—C7—N2	123.86 (10)	C15—C16—H16A	109.7
N1—C7—N2	114.31 (10)	O2—C16—H16B	109.7
O1—C8—N2	119.47 (11)	C15—C16—H16B	109.7
O1—C8—C9	124.96 (11)	H16A—C16—H16B	108.2
N2—C8—C9	115.56 (10)	C7—N1—C4	128.75 (10)
C10—C9—C14	120.21 (11)	C7—N1—H1	115.3 (9)
C10—C9—C8	118.50 (11)	C4—N1—H1	113.5 (9)
C14—C9—C8	121.29 (11)	C8—N2—C7	120.89 (10)
N3—C10—C9	122.90 (10)	C8—N2—C15	116.33 (10)
N3—C10—C11	118.21 (11)	C7—N2—C15	122.56 (10)
C9—C10—C11	118.75 (11)	C7—N3—C10	117.72 (10)
C12—C11—C10	120.09 (12)	C16—O2—H2A	107.5 (13)
C6—C1—C2—C3	0.31 (19)	C12—C13—C14—C9	0.1 (2)
F1—C1—C2—C3	179.97 (10)	C10—C9—C14—C13	−0.76 (19)
C1—C2—C3—C4	0.08 (18)	C8—C9—C14—C13	179.16 (12)
C2—C3—C4—C5	−0.34 (18)	N2—C15—C16—O2	−74.18 (14)
C2—C3—C4—N1	178.41 (11)	N3—C7—N1—C4	−3.84 (19)
C3—C4—C5—C6	0.23 (18)	N2—C7—N1—C4	176.74 (11)
N1—C4—C5—C6	−178.39 (11)	C5—C4—N1—C7	−3.0 (2)
F1—C1—C6—C5	179.92 (11)	C3—C4—N1—C7	178.32 (11)
C2—C1—C6—C5	−0.42 (19)	O1—C8—N2—C7	−174.16 (11)
C4—C5—C6—C1	0.14 (19)	C9—C8—N2—C7	6.98 (16)
O1—C8—C9—C10	−179.80 (11)	O1—C8—N2—C15	11.04 (16)
N2—C8—C9—C10	−1.02 (16)	C9—C8—N2—C15	−167.81 (10)
O1—C8—C9—C14	0.28 (19)	N3—C7—N2—C8	−9.29 (17)
N2—C8—C9—C14	179.06 (11)	N1—C7—N2—C8	170.11 (10)
C14—C9—C10—N3	176.35 (11)	N3—C7—N2—C15	165.17 (11)
C8—C9—C10—N3	−3.57 (17)	N1—C7—N2—C15	−15.43 (15)
C14—C9—C10—C11	0.73 (17)	C16—C15—N2—C8	−94.13 (13)
C8—C9—C10—C11	−179.20 (10)	C16—C15—N2—C7	91.16 (14)
N3—C10—C11—C12	−175.91 (11)	N1—C7—N3—C10	−174.89 (10)
C9—C10—C11—C12	−0.08 (18)	N2—C7—N3—C10	4.47 (17)
C10—C11—C12—C13	−0.6 (2)	C9—C10—N3—C7	1.96 (17)
C11—C12—C13—C14	0.5 (2)	C11—C10—N3—C7	177.61 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···N3	0.93	2.28	2.8807 (16)	122
N1—H1···O2	0.88 (1)	1.98 (1)	2.8253 (14)	160 (1)
O2—H2A···O1i	0.84 (1)	1.91 (1)	2.7426 (13)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯N3	0.93	2.28	2.8807 (16)	122
N1—H1⋯O2	0.881 (9)	1.982 (10)	2.8253 (14)	159.7 (13)
O2—H2A⋯O1i	0.837 (9)	1.909 (10)	2.7426 (13)	173.6 (18)

Symmetry code: (i) .