3-(4-Fluoro­phen­yl)-2-morpholinoquinazolin-4(3H)-one

Cai, C.-Q.; Luo, H.; He, P.; Yang, Z.-Z..

doi:10.1107/S1600536807027535

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3-(4-Fluorophenyl)-2-morpholinoquinazolin-4(3H)-one

C.-Q. Cai, H. Luo, P. He and Z.-Z. Yang

The title compound, C₁₈H₁₆FN₃O₂, was obtained via the aza-Wittig reaction. The quinazolinone ring system is almost planar and makes a dihedral angle of 67.09 (8)° with the substituent benzene ring. The structure is stabilized by a weak C—H

O hydrogen bond and C—H

π interactions.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027535/is2172sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027535/is2172Isup2.hkl Contains datablock I

CCDC reference: 654941

checkCIF report

Key indicators

Single-crystal X-ray study
T = 291 K
Mean (C-C) = 0.003 Å
R factor = 0.059
wR factor = 0.158
Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT601_ALERT_2_B Structure Contains Solvent Accessible VOIDS of .     150.00 A   3 

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   0 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Quinazolinones are important heterocyclic compounds which exhibit good biological and pharmaceutical activities, including anti-inflammotory, antifunga, anticancer and AMPA-receptor antagonistic properties (Shiba et al., 1997). As part of our work on the preparation of potentially active heterocycles (Ding et al., 2000), we have obtained the title compound, (I).

Within the molecule of (I), the bond lengths and angles present no unusual features. In (I), the quinazolinone ring system is approximately planar, with a maximum deviation of 0.060 (1) and 0.028 (1) Å for atoms N1 and N2, respectively; the C13—C18 benzene ring is twisted with respect to it, with a dihedral angle of 67.09 (8)°. The morpholine ring shows a distorted chair conformation [φ = 341.64 (1)° and θ = 176.25 (1)°, Puckering Amplitude = 0.586 (1) Å] (Cremer & Pople, 1975). The structure is stabilized by a weak C—H···O hydrogen bond and C—H···π interactions (Table 1); Cg1, Cg2 and Cg3 are the centroids of C1—C6, N1/C7/C5/C6/N2/C8 and C13—C18 rings, respectively..

Related literature top

Biological and pharmaceutical activities have been described by Shiba et al. (1997) and the preparation of potentially active heterocycles has been described by Ding et al. (2000). For ring-puckering analysis, see Cremer & Pople (1975).

Experimental top

To a solution of iminophosphorane (1.45 g, 3 mmol) in anhydrous dichloromethane (15 ml) was added 4-fluorophenyl isocyanate (3 mmol) under dry nitrogen at room temperature. The reaction mixture was left unstirred for 8 h at room temperature and then the solvent was removed under reduced pressure and ether-petroleum ether (1:2 v/v, 20 ml) was added to precipitate triphenylphosphine oxide. After filtration, the solution of carbodiimide was added to a solution of diethyl-amine in anhydrous dichloromethane. After stirring the reaction mixture for 8 h, the solvent was removed under reduced pressure and the residue was recrystallized from ethanol to give the title compound, (I), in a yield of 90% (m.p. 394–396 K). Single crystals suitable for X-ray diffraction were obtained by recrystallization from a mixed solvent of hexane and dichloromethane (1:3 v/v) at room temperature.

Structure description top

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom labelling scheme and with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. A partial packing view of (I). Dashed lines indicate the C—H···π interactions.

3-(4-Fluorophenyl)-2-morpholinoquinazolin-4(3H)-one top

Crystal data top

C₁₈H₁₆FN₃O₂	D_x = 1.289 Mg m⁻³
M_r = 325.34	Mo Kα radiation, λ = 0.71073 Å
Tetragonal, I4₁/a	Cell parameters from 8691 reflections
Hall symbol: -I 4ad	θ = 2.5–24.9°
a = 22.9526 (7) Å	µ = 0.09 mm⁻¹
c = 12.7318 (7) Å	T = 291 K
V = 6707.4 (5) Å³	Plate, colourless
Z = 16	0.30 × 0.20 × 0.20 mm
F(000) = 2720

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3033 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.081
Graphite monochromator	θ_max = 27.0°, θ_min = 1.8°
φ and ω scans	h = −29→29
37145 measured reflections	k = −29→29
3665 independent reflections	l = −16→16

Refinement top

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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.158	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0883P)² + 2.6139P] where P = (F_o² + 2F_c²)/3
3665 reflections	(Δ/σ)_max = 0.009
217 parameters	Δρ_max = 0.29 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₈H₁₆FN₃O₂	Z = 16
M_r = 325.34	Mo Kα radiation
Tetragonal, I4₁/a	µ = 0.09 mm⁻¹
a = 22.9526 (7) Å	T = 291 K
c = 12.7318 (7) Å	0.30 × 0.20 × 0.20 mm
V = 6707.4 (5) Å³

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3033 reflections with I > 2σ(I)
37145 measured reflections	R_int = 0.081
3665 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.059	0 restraints
wR(F²) = 0.158	H-atom parameters constrained
S = 1.06	Δρ_max = 0.29 e Å⁻³
3665 reflections	Δρ_min = −0.34 e Å⁻³
217 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.59565 (8)	0.62432 (8)	−0.12006 (15)	0.0401 (4)
H1	0.5653	0.6505	−0.1093	0.048*
C2	0.63280 (9)	0.63192 (9)	−0.20375 (15)	0.0430 (5)
H2	0.6271	0.6630	−0.2495	0.052*
C3	0.67875 (9)	0.59369 (9)	−0.22054 (15)	0.0427 (5)
H3	0.7034	0.5990	−0.2777	0.051*
C4	0.68773 (8)	0.54821 (8)	−0.15293 (15)	0.0375 (4)
H4	0.7189	0.5230	−0.1637	0.045*
C5	0.65010 (7)	0.53949 (7)	−0.06747 (13)	0.0305 (4)
C6	0.60337 (7)	0.57732 (7)	−0.05088 (13)	0.0310 (4)
C7	0.65773 (7)	0.48957 (8)	0.00124 (13)	0.0319 (4)
C8	0.57321 (7)	0.52771 (7)	0.09563 (13)	0.0281 (4)
C9	0.56338 (8)	0.52223 (9)	0.28622 (13)	0.0356 (4)
H9A	0.5693	0.5627	0.3058	0.043*
H9B	0.6009	0.5028	0.2863	0.043*
C10	0.52302 (8)	0.49319 (10)	0.36305 (15)	0.0429 (5)
H10A	0.5182	0.4526	0.3439	0.051*
H10B	0.5399	0.4947	0.4328	0.051*
C11	0.48082 (8)	0.54901 (9)	0.18113 (14)	0.0383 (4)
H11A	0.4629	0.5465	0.1122	0.046*
H11B	0.4863	0.5898	0.1984	0.046*
C12	0.44237 (8)	0.52015 (10)	0.26214 (14)	0.0434 (5)
H12A	0.4051	0.5400	0.2642	0.052*
H12B	0.4354	0.4801	0.2416	0.052*
C13	0.61453 (7)	0.43071 (7)	0.14019 (13)	0.0311 (4)
C14	0.65930 (8)	0.41819 (8)	0.20947 (14)	0.0363 (4)
H14	0.6903	0.4440	0.2172	0.044*
C15	0.65774 (9)	0.36692 (9)	0.26745 (15)	0.0445 (5)
H15	0.6876	0.3577	0.3140	0.053*
C16	0.61141 (10)	0.33061 (9)	0.25439 (18)	0.0522 (6)
C17	0.56688 (10)	0.34217 (10)	0.1861 (2)	0.0601 (6)
H17	0.5358	0.3164	0.1796	0.072*
C18	0.56866 (9)	0.39266 (9)	0.12670 (17)	0.0449 (5)
H18	0.5394	0.4008	0.0784	0.054*
F1	0.60879 (7)	0.28091 (7)	0.31230 (15)	0.0853 (5)
N1	0.61561 (6)	0.48459 (6)	0.08071 (10)	0.0288 (3)
N2	0.56556 (6)	0.57138 (6)	0.03353 (11)	0.0338 (3)
N3	0.53697 (6)	0.51878 (6)	0.18116 (11)	0.0309 (3)
O1	0.69568 (6)	0.45289 (6)	−0.00868 (12)	0.0501 (4)
O2	0.46772 (6)	0.52110 (7)	0.36408 (10)	0.0459 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0392 (10)	0.0398 (10)	0.0414 (10)	0.0016 (8)	−0.0009 (8)	0.0097 (8)
C2	0.0477 (11)	0.0422 (11)	0.0390 (10)	−0.0081 (9)	−0.0020 (8)	0.0140 (8)
C3	0.0434 (11)	0.0512 (12)	0.0334 (9)	−0.0132 (9)	0.0089 (8)	0.0047 (8)
C4	0.0345 (9)	0.0406 (10)	0.0374 (10)	−0.0032 (8)	0.0064 (7)	−0.0011 (8)
C5	0.0290 (8)	0.0332 (9)	0.0292 (8)	−0.0039 (7)	0.0013 (6)	−0.0014 (7)
C6	0.0326 (9)	0.0315 (9)	0.0288 (8)	−0.0027 (7)	−0.0014 (7)	0.0021 (7)
C7	0.0278 (8)	0.0340 (9)	0.0340 (9)	0.0004 (7)	0.0030 (7)	−0.0003 (7)
C8	0.0251 (8)	0.0326 (8)	0.0266 (8)	−0.0002 (6)	−0.0007 (6)	−0.0003 (6)
C9	0.0293 (9)	0.0485 (11)	0.0291 (9)	0.0012 (8)	0.0000 (7)	−0.0041 (8)
C10	0.0418 (11)	0.0580 (12)	0.0289 (9)	0.0035 (9)	0.0033 (8)	0.0037 (8)
C11	0.0318 (9)	0.0481 (11)	0.0351 (9)	0.0099 (8)	0.0036 (7)	0.0015 (8)
C12	0.0317 (9)	0.0631 (13)	0.0354 (10)	0.0017 (9)	0.0043 (7)	−0.0038 (9)
C13	0.0328 (9)	0.0308 (9)	0.0298 (8)	0.0035 (7)	0.0020 (7)	0.0045 (7)
C14	0.0363 (9)	0.0380 (10)	0.0346 (9)	0.0050 (8)	−0.0031 (7)	0.0001 (7)
C15	0.0479 (11)	0.0508 (12)	0.0347 (10)	0.0151 (9)	−0.0043 (8)	0.0071 (8)
C16	0.0576 (13)	0.0409 (11)	0.0581 (13)	0.0072 (10)	0.0063 (11)	0.0215 (10)
C17	0.0500 (13)	0.0445 (12)	0.0859 (17)	−0.0114 (10)	−0.0091 (12)	0.0211 (12)
C18	0.0391 (10)	0.0405 (11)	0.0552 (12)	−0.0031 (8)	−0.0098 (9)	0.0106 (9)
F1	0.0905 (11)	0.0613 (9)	0.1042 (13)	0.0037 (8)	0.0010 (9)	0.0498 (9)
N1	0.0270 (7)	0.0314 (7)	0.0282 (7)	0.0016 (6)	0.0006 (5)	0.0029 (6)
N2	0.0335 (8)	0.0345 (8)	0.0333 (8)	0.0040 (6)	0.0053 (6)	0.0041 (6)
N3	0.0268 (7)	0.0390 (8)	0.0270 (7)	0.0042 (6)	0.0028 (5)	0.0029 (6)
O1	0.0454 (8)	0.0460 (8)	0.0591 (9)	0.0174 (6)	0.0204 (7)	0.0123 (7)
O2	0.0357 (7)	0.0717 (10)	0.0304 (7)	0.0037 (7)	0.0073 (5)	−0.0033 (6)

Geometric parameters (Å, º) top

C1—C2	1.376 (3)	C10—H10A	0.9700
C1—C6	1.404 (2)	C10—H10B	0.9700
C1—H1	0.9300	C11—N3	1.464 (2)
C2—C3	1.388 (3)	C11—C12	1.510 (3)
C2—H2	0.9300	C11—H11A	0.9700
C3—C4	1.369 (3)	C11—H11B	0.9700
C3—H3	0.9300	C12—O2	1.423 (2)
C4—C5	1.404 (2)	C12—H12A	0.9700
C4—H4	0.9300	C12—H12B	0.9700
C5—C6	1.396 (2)	C13—C18	1.379 (3)
C5—C7	1.452 (2)	C13—C14	1.384 (2)
C6—N2	1.388 (2)	C13—N1	1.450 (2)
C7—O1	1.218 (2)	C14—C15	1.390 (3)
C7—N1	1.404 (2)	C14—H14	0.9300
C8—N2	1.289 (2)	C15—C16	1.361 (3)
C8—N3	1.386 (2)	C15—H15	0.9300
C8—N1	1.401 (2)	C16—F1	1.360 (2)
C9—N3	1.471 (2)	C16—C17	1.368 (3)
C9—C10	1.503 (3)	C17—C18	1.384 (3)
C9—H9A	0.9700	C17—H17	0.9300
C9—H9B	0.9700	C18—H18	0.9300
C10—O2	1.422 (2)

C2—C1—C6	120.34 (18)	N3—C11—H11A	110.1
C2—C1—H1	119.8	C12—C11—H11A	110.1
C6—C1—H1	119.8	N3—C11—H11B	110.1
C1—C2—C3	120.66 (17)	C12—C11—H11B	110.1
C1—C2—H2	119.7	H11A—C11—H11B	108.5
C3—C2—H2	119.7	O2—C12—C11	112.17 (16)
C4—C3—C2	119.97 (17)	O2—C12—H12A	109.2
C4—C3—H3	120.0	C11—C12—H12A	109.2
C2—C3—H3	120.0	O2—C12—H12B	109.2
C3—C4—C5	120.24 (17)	C11—C12—H12B	109.2
C3—C4—H4	119.9	H12A—C12—H12B	107.9
C5—C4—H4	119.9	C18—C13—C14	120.98 (16)
C6—C5—C4	120.09 (16)	C18—C13—N1	119.23 (15)
C6—C5—C7	119.49 (15)	C14—C13—N1	119.79 (15)
C4—C5—C7	120.35 (16)	C13—C14—C15	119.68 (18)
N2—C6—C5	122.43 (15)	C13—C14—H14	120.2
N2—C6—C1	118.84 (16)	C15—C14—H14	120.2
C5—C6—C1	118.68 (16)	C16—C15—C14	118.28 (18)
O1—C7—N1	120.72 (16)	C16—C15—H15	120.9
O1—C7—C5	124.69 (16)	C14—C15—H15	120.9
N1—C7—C5	114.54 (14)	F1—C16—C15	118.8 (2)
N2—C8—N3	121.03 (15)	F1—C16—C17	118.3 (2)
N2—C8—N1	124.13 (14)	C15—C16—C17	122.85 (18)
N3—C8—N1	114.77 (14)	C16—C17—C18	119.2 (2)
N3—C9—C10	108.30 (14)	C16—C17—H17	120.4
N3—C9—H9A	110.0	C18—C17—H17	120.4
C10—C9—H9A	110.0	C13—C18—C17	119.01 (19)
N3—C9—H9B	110.0	C13—C18—H18	120.5
C10—C9—H9B	110.0	C17—C18—H18	120.5
H9A—C9—H9B	108.4	C8—N1—C7	121.23 (14)
O2—C10—C9	110.88 (16)	C8—N1—C13	121.31 (13)
O2—C10—H10A	109.5	C7—N1—C13	117.23 (13)
C9—C10—H10A	109.5	C8—N2—C6	117.79 (15)
O2—C10—H10B	109.5	C8—N3—C11	117.28 (14)
C9—C10—H10B	109.5	C8—N3—C9	117.35 (13)
H10A—C10—H10B	108.1	C11—N3—C9	109.72 (13)
N3—C11—C12	107.85 (15)	C10—O2—C12	110.48 (14)

C6—C1—C2—C3	−0.7 (3)	N2—C8—N1—C7	7.1 (2)
C1—C2—C3—C4	−0.6 (3)	N3—C8—N1—C7	−176.00 (14)
C2—C3—C4—C5	1.0 (3)	N2—C8—N1—C13	−167.20 (16)
C3—C4—C5—C6	−0.2 (3)	N3—C8—N1—C13	9.7 (2)
C3—C4—C5—C7	176.81 (17)	O1—C7—N1—C8	177.33 (17)
C4—C5—C6—N2	−178.68 (16)	C5—C7—N1—C8	−5.0 (2)
C7—C5—C6—N2	4.3 (3)	O1—C7—N1—C13	−8.2 (2)
C4—C5—C6—C1	−1.0 (3)	C5—C7—N1—C13	169.47 (14)
C7—C5—C6—C1	−178.05 (16)	C18—C13—N1—C8	64.6 (2)
C2—C1—C6—N2	179.18 (17)	C14—C13—N1—C8	−115.37 (18)
C2—C1—C6—C5	1.4 (3)	C18—C13—N1—C7	−109.90 (19)
C6—C5—C7—O1	177.26 (18)	C14—C13—N1—C7	70.1 (2)
C4—C5—C7—O1	0.3 (3)	N3—C8—N2—C6	−179.62 (15)
C6—C5—C7—N1	−0.3 (2)	N1—C8—N2—C6	−2.9 (2)
C4—C5—C7—N1	−177.26 (15)	C5—C6—N2—C8	−2.8 (2)
N3—C9—C10—O2	−59.7 (2)	C1—C6—N2—C8	179.56 (16)
N3—C11—C12—O2	57.9 (2)	N2—C8—N3—C11	17.8 (2)
C18—C13—C14—C15	−0.9 (3)	N1—C8—N3—C11	−159.21 (15)
N1—C13—C14—C15	179.11 (16)	N2—C8—N3—C9	−116.15 (18)
C13—C14—C15—C16	−0.5 (3)	N1—C8—N3—C9	66.8 (2)
C14—C15—C16—F1	−178.64 (19)	C12—C11—N3—C8	163.67 (15)
C14—C15—C16—C17	0.7 (4)	C12—C11—N3—C9	−59.11 (19)
F1—C16—C17—C18	179.8 (2)	C10—C9—N3—C8	−162.18 (16)
C15—C16—C17—C18	0.4 (4)	C10—C9—N3—C11	60.63 (19)
C14—C13—C18—C17	2.0 (3)	C9—C10—O2—C12	58.3 (2)
N1—C13—C18—C17	−177.98 (19)	C11—C12—O2—C10	−57.8 (2)
C16—C17—C18—C13	−1.8 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1ⁱ	0.93	2.57	3.306 (2)	137
C9—H9A···Cg3ⁱ	0.97	2.85	3.673 (2)	143
C11—H11A···Cg2ⁱⁱ	0.97	2.96	3.759 (2)	141
C12—H12A···Cg1ⁱⁱⁱ	0.97	2.72	3.548 (2)	143
C12—H12B···Cg1ⁱⁱ	0.97	2.68	3.492 (2)	141

Symmetry codes: (i) y+1/4, −x+5/4, z+1/4; (ii) −x+1, −y+1, −z; (iii) y−1/4, −x+5/4, −z+1/4.

Experimental details

Crystal data
Chemical formula	C₁₈H₁₆FN₃O₂
M_r	325.34
Crystal system, space group	Tetragonal, I4₁/a
Temperature (K)	291
a, c (Å)	22.9526 (7), 12.7318 (7)
V (Å³)	6707.4 (5)
Z	16
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	37145, 3665, 3033
R_int	0.081
(sin θ/λ)_max (Å⁻¹)	0.638

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.059, 0.158, 1.06
No. of reflections	3665
No. of parameters	217
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.29, −0.34

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXTL (Sheldrick, 2001).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1ⁱ	0.93	2.57	3.306 (2)	137
C9—H9A···Cg3ⁱ	0.97	2.85	3.673 (2)	143
C11—H11A···Cg2ⁱⁱ	0.97	2.96	3.759 (2)	141
C12—H12A···Cg1ⁱⁱⁱ	0.97	2.72	3.548 (2)	143
C12—H12B···Cg1ⁱⁱ	0.97	2.68	3.492 (2)	141

Symmetry codes: (i) y+1/4, −x+5/4, z+1/4; (ii) −x+1, −y+1, −z; (iii) y−1/4, −x+5/4, −z+1/4.

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