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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o638.
Published online 2009 February 28. doi:  10.1107/S1600536809006254
PMCID: PMC2968625

2-(4-Fluoro­anilino)-3-(2-hydroxy­ethyl)quinazolin-4(3H)-one

Abstract

The mol­ecular and crystal structures of the title compound, C16H14FN3O2, are stabilized by intra­molecular N—H(...)O and inter­molecular O—H(...)O hydrogen bonds. The existence of non-classical intra­molecular 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 [triangle]). For the synthesis of quinazolinone and thienopyrimidinones, see: Yang et al. (2008 [triangle]). For synthesis, drug discovery and crystal structures, see: Yang & Wu (2008 [triangle]); Wang et al. (2008 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o638-scheme1.jpg

Experimental

Crystal data

  • C16H14FN3O2
  • M r = 299.30
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o638-efi4.jpg
  • 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 [triangle]); cell refinement: SAINT (Bruker, 2007 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

Acknowledgments

We acknowledge financial support by the Huangshi Institute of Technology (grant Nos. 08yjz23B & 07yjz18B), P. R. China.

supplementary crystallographic information

Comment

Quinazolone derivatives have evoked considerable attention in recent years as these are endowed with wide range of pharmaceutical activities. 3H–Quinazolin–4–one represents a useful nucleus for preparation of some new sedative/hypnotic and anticonvulsant agents. Of the various quinazolines reported, the N3 and C7 disubstituted quinazolines exhibit interesting pharmacological activities like analgesic, anti–inflammatory, antibacterial and anticonvulsant activities (Usha et al., 2006). In connection with our ongoing heterocyclic synthesis and drug discovery project (Yang & Wu, 2008), we have focused on the synthesis of quinazolinone and thienopyrimidinones (Wang et al., 2008; Yang et al., 2008). Herein, the title compound was synthesied and its molecular (Fig. 1) and crystal structures were determined. An intramolecular N1—H1···O2 and non–classical C5—H5···N3 hydrogen bonds provide the conformation of the molecule - dihedral angle between the fluoro–substituted benzene ring and pyrimidinone rings as 7.9 (1)°. In the crystal structure, intermolecular O2—H2a···O1i hydrogen bonds link of molecules into chains (see Tab. 1 and Fig. 2). Symmetry code: (i) -x+5/2, y-1/2, -z+1/2.

Experimental

To a solution of 2–ethoxycarbonyliminophosphorane (1.27 g, 3.0 mmol) in 10 ml anhydrous THF, 4–fluorophenyl isocyanate (0.41 g, 3.0 mmol) was added dropwise at room temperature. The reaction mixture was left unstirred for 6 h at 273–278 K, whereafter the above resulting solution was added dropwise to a solution of ethanolamine (0.18 g, 3 mmol) in 5 ml anhydrous THF. The reaction mixture was stirred overnight at room temperature, the solvent was removed under reduced pressure and the residue was recrystallized from C2H4Cl2/CH3OH (1:1/v:v) to give colourless crystals of the title compound. Yield 89%.

Refinement

The C–bonded H atoms were placed in calculated positions with C—H = 0.93 Å for aromatic, C—H = 0.97 Å for methylene and refined in the riding model approximation. The positional parameters of N– and O–bonded H atoms were found from difference Fourier map and refined independently. For all H atoms Uiso(H) = 1.2Ueq(C, N) and Uiso(H) = 1.5Ueq(O).

Figures

Fig. 1.
View of the title molecule with the atom–labeling scheme. Dispalcement ellipsoids are drawn at the 50% probability level. H at6oms are presented as a small spheres of arbitrary radius. Intramolecular hydrogen bonds are drawn by dashed lines.
Fig. 2.
Part of the crystal structure of the title compound showing intermolecular hydrogen bonds as dashed lines. Symmetry code: (i) -x+5/2, y-1/2, -z+1/2.

Crystal data

C16H14FN3O2F(000) = 624
Mr = 299.30Dx = 1.450 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3320 reflections
a = 8.5737 (8) Åθ = 2.3–29.2°
b = 10.8268 (10) ŵ = 0.11 mm1
c = 15.2490 (13) ÅT = 273 K
β = 104.407 (1)°Block, colourless
V = 1371.0 (2) Å30.10 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer2475 reflections with I > 2σ(I)
Radiation source: Fine–focus sealed tubeRint = 0.021
Graphiteθmax = 27.0°, θmin = 2.3°
[var phi] and ω scansh = −10→10
8342 measured reflectionsk = −12→13
2976 independent reflectionsl = −19→14

Refinement

Refinement on F2Primary atom site location: Direct
Least-squares matrix: FullSecondary atom site location: Difmap
R[F2 > 2σ(F2)] = 0.037Hydrogen site location: Geom
wR(F2) = 0.102H atoms treated by a mixture of independent and constrained refinement
S = 1.06w = 1/[σ2(Fo2) + (0.0546P)2 + 0.157P] where P = (Fo2 + 2Fc2)/3
2976 reflections(Δ/σ)max = 0.001
205 parametersΔρmax = 0.13 e Å3
2 restraintsΔρmin = −0.23 e Å3

Special details

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.

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

xyzUiso*/Ueq
C10.56770 (14)0.34529 (11)−0.09177 (9)0.0442 (3)
C20.59291 (15)0.34162 (11)0.00070 (9)0.0455 (3)
H20.54440.28130.02830.055*
C30.69136 (15)0.42908 (11)0.05135 (8)0.0427 (3)
H30.70960.42760.11410.051*
C40.76459 (13)0.52003 (10)0.01077 (8)0.0379 (3)
C50.73709 (15)0.52084 (12)−0.08302 (8)0.0438 (3)
H50.78520.5807−0.11130.053*
C60.63794 (15)0.43247 (12)−0.13419 (8)0.0458 (3)
H60.61930.4325−0.19690.055*
C70.94732 (13)0.70237 (10)0.05017 (7)0.0377 (3)
C81.13407 (14)0.86392 (11)0.11798 (8)0.0418 (3)
C91.15360 (14)0.88561 (11)0.02741 (8)0.0402 (3)
C101.06202 (13)0.81559 (11)−0.04382 (8)0.0389 (3)
C111.08192 (15)0.83508 (12)−0.13148 (8)0.0462 (3)
H111.02200.7892−0.17980.055*
C121.18945 (16)0.92159 (13)−0.14591 (9)0.0520 (3)
H121.20250.9334−0.20410.062*
C131.27943 (17)0.99209 (13)−0.07485 (10)0.0549 (3)
H131.35141.0510−0.08570.066*
C141.26168 (16)0.97446 (12)0.01099 (10)0.0504 (3)
H141.32151.02160.05860.060*
C150.97517 (16)0.76912 (12)0.21207 (8)0.0450 (3)
H15A0.86170.74840.19990.054*
H15B0.98890.85050.23950.054*
C161.06872 (18)0.67775 (13)0.27916 (8)0.0526 (3)
H16A1.18280.68610.28270.063*
H16B1.05210.69440.33870.063*
F10.46983 (11)0.25850 (8)−0.14287 (6)0.0651 (3)
N10.85952 (13)0.60633 (10)0.07009 (7)0.0439 (2)
H10.8863 (16)0.5818 (12)0.1269 (6)0.053*
N21.02153 (12)0.77481 (9)0.12481 (6)0.0393 (2)
N30.96041 (12)0.72240 (9)−0.03130 (6)0.0411 (2)
O11.20713 (12)0.91951 (9)0.18653 (6)0.0565 (3)
O21.01772 (12)0.55593 (9)0.25230 (6)0.0546 (3)
H2A1.0973 (16)0.5093 (14)0.2698 (12)0.082*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0436 (6)0.0404 (6)0.0481 (7)−0.0004 (5)0.0105 (5)−0.0022 (5)
C20.0492 (7)0.0396 (6)0.0504 (7)0.0018 (5)0.0174 (6)0.0082 (5)
C30.0499 (7)0.0442 (6)0.0356 (6)0.0072 (5)0.0135 (5)0.0067 (5)
C40.0379 (6)0.0404 (6)0.0360 (6)0.0046 (5)0.0104 (5)0.0012 (5)
C50.0492 (7)0.0480 (7)0.0357 (6)−0.0038 (5)0.0132 (5)0.0024 (5)
C60.0508 (7)0.0519 (7)0.0352 (6)−0.0028 (6)0.0114 (5)−0.0017 (5)
C70.0370 (6)0.0411 (6)0.0333 (6)0.0052 (5)0.0058 (4)0.0015 (5)
C80.0416 (6)0.0426 (6)0.0409 (6)0.0040 (5)0.0094 (5)−0.0044 (5)
C90.0388 (6)0.0399 (6)0.0420 (6)0.0059 (5)0.0102 (5)0.0020 (5)
C100.0377 (6)0.0406 (6)0.0376 (6)0.0065 (5)0.0080 (5)0.0053 (5)
C110.0476 (7)0.0538 (7)0.0351 (6)0.0046 (6)0.0060 (5)0.0081 (5)
C120.0531 (7)0.0602 (8)0.0442 (7)0.0058 (6)0.0149 (6)0.0147 (6)
C130.0513 (8)0.0542 (8)0.0607 (9)−0.0035 (6)0.0168 (6)0.0112 (7)
C140.0489 (7)0.0483 (7)0.0536 (8)−0.0022 (6)0.0121 (6)−0.0010 (6)
C150.0535 (7)0.0494 (7)0.0348 (6)0.0053 (6)0.0160 (5)−0.0031 (5)
C160.0621 (8)0.0616 (8)0.0327 (6)0.0034 (6)0.0092 (6)−0.0009 (6)
F10.0736 (6)0.0599 (5)0.0592 (5)−0.0229 (4)0.0116 (4)−0.0068 (4)
N10.0521 (6)0.0494 (6)0.0297 (5)−0.0036 (5)0.0092 (4)0.0026 (4)
N20.0434 (5)0.0436 (5)0.0316 (5)0.0037 (4)0.0104 (4)−0.0013 (4)
N30.0436 (5)0.0456 (6)0.0331 (5)0.0000 (4)0.0077 (4)0.0028 (4)
O10.0601 (6)0.0639 (6)0.0450 (5)−0.0115 (5)0.0123 (4)−0.0152 (4)
O20.0629 (6)0.0552 (6)0.0421 (5)0.0091 (4)0.0062 (4)0.0055 (4)

Geometric parameters (Å, °)

C1—C61.3659 (17)C9—C141.4007 (17)
C1—F11.3670 (14)C10—N31.3771 (15)
C1—C21.3729 (18)C10—C111.4050 (16)
C2—C31.3716 (18)C11—C121.3699 (19)
C2—H20.9300C11—H110.9300
C3—C41.3929 (16)C12—C131.391 (2)
C3—H30.9300C12—H120.9300
C4—C51.3904 (16)C13—C141.3683 (19)
C4—N11.4098 (15)C13—H130.9300
C5—C61.3846 (17)C14—H140.9300
C5—H50.9300C15—N21.4817 (14)
C6—H60.9300C15—C161.5035 (18)
C7—N31.2932 (14)C15—H15A0.9700
C7—N11.3616 (15)C15—H15B0.9700
C7—N21.3983 (15)C16—O21.4174 (17)
C8—O11.2335 (14)C16—H16A0.9700
C8—N21.3866 (15)C16—H16B0.9700
C8—C91.4511 (16)N1—H10.881 (9)
C9—C101.3952 (16)O2—H2A0.837 (9)
C6—C1—F1119.04 (11)C12—C11—H11120.0
C6—C1—C2122.08 (12)C10—C11—H11120.0
F1—C1—C2118.88 (11)C11—C12—C13120.99 (12)
C3—C2—C1118.42 (11)C11—C12—H12119.5
C3—C2—H2120.8C13—C12—H12119.5
C1—C2—H2120.8C14—C13—C12119.76 (12)
C2—C3—C4121.34 (11)C14—C13—H13120.1
C2—C3—H3119.3C12—C13—H13120.1
C4—C3—H3119.3C13—C14—C9120.19 (13)
C5—C4—C3118.79 (11)C13—C14—H14119.9
C5—C4—N1125.37 (11)C9—C14—H14119.9
C3—C4—N1115.82 (10)N2—C15—C16114.93 (10)
C6—C5—C4119.90 (11)N2—C15—H15A108.5
C6—C5—H5120.0C16—C15—H15A108.5
C4—C5—H5120.0N2—C15—H15B108.5
C1—C6—C5119.46 (11)C16—C15—H15B108.5
C1—C6—H6120.3H15A—C15—H15B107.5
C5—C6—H6120.3O2—C16—C15109.98 (11)
N3—C7—N1121.83 (11)O2—C16—H16A109.7
N3—C7—N2123.86 (10)C15—C16—H16A109.7
N1—C7—N2114.31 (10)O2—C16—H16B109.7
O1—C8—N2119.47 (11)C15—C16—H16B109.7
O1—C8—C9124.96 (11)H16A—C16—H16B108.2
N2—C8—C9115.56 (10)C7—N1—C4128.75 (10)
C10—C9—C14120.21 (11)C7—N1—H1115.3 (9)
C10—C9—C8118.50 (11)C4—N1—H1113.5 (9)
C14—C9—C8121.29 (11)C8—N2—C7120.89 (10)
N3—C10—C9122.90 (10)C8—N2—C15116.33 (10)
N3—C10—C11118.21 (11)C7—N2—C15122.56 (10)
C9—C10—C11118.75 (11)C7—N3—C10117.72 (10)
C12—C11—C10120.09 (12)C16—O2—H2A107.5 (13)
C6—C1—C2—C30.31 (19)C12—C13—C14—C90.1 (2)
F1—C1—C2—C3179.97 (10)C10—C9—C14—C13−0.76 (19)
C1—C2—C3—C40.08 (18)C8—C9—C14—C13179.16 (12)
C2—C3—C4—C5−0.34 (18)N2—C15—C16—O2−74.18 (14)
C2—C3—C4—N1178.41 (11)N3—C7—N1—C4−3.84 (19)
C3—C4—C5—C60.23 (18)N2—C7—N1—C4176.74 (11)
N1—C4—C5—C6−178.39 (11)C5—C4—N1—C7−3.0 (2)
F1—C1—C6—C5179.92 (11)C3—C4—N1—C7178.32 (11)
C2—C1—C6—C5−0.42 (19)O1—C8—N2—C7−174.16 (11)
C4—C5—C6—C10.14 (19)C9—C8—N2—C76.98 (16)
O1—C8—C9—C10−179.80 (11)O1—C8—N2—C1511.04 (16)
N2—C8—C9—C10−1.02 (16)C9—C8—N2—C15−167.81 (10)
O1—C8—C9—C140.28 (19)N3—C7—N2—C8−9.29 (17)
N2—C8—C9—C14179.06 (11)N1—C7—N2—C8170.11 (10)
C14—C9—C10—N3176.35 (11)N3—C7—N2—C15165.17 (11)
C8—C9—C10—N3−3.57 (17)N1—C7—N2—C15−15.43 (15)
C14—C9—C10—C110.73 (17)C16—C15—N2—C8−94.13 (13)
C8—C9—C10—C11−179.20 (10)C16—C15—N2—C791.16 (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—C104.47 (17)
C10—C11—C12—C13−0.6 (2)C9—C10—N3—C71.96 (17)
C11—C12—C13—C140.5 (2)C11—C10—N3—C7177.61 (10)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C5—H5···N30.932.282.8807 (16)122
N1—H1···O20.88 (1)1.98 (1)2.8253 (14)160 (1)
O2—H2A···O1i0.84 (1)1.91 (1)2.7426 (13)174 (2)

Symmetry codes: (i) −x+5/2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: RK2120).

References

  • Bruker (2007). SMART and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Usha, A., Swati, O., Dinesh, B. & Ganpat, L. T. (2006). ARKIVOC, xiii, 83–89.
  • Wang, H.-L., Yang, X.-H. & Wu, M.-H. (2008). Acta Cryst. E64, o2325. [PMC free article] [PubMed]
  • Yang, X.-H. & Wu, M.-H. (2008). Acta Cryst. E64, o2240. [PMC free article] [PubMed]
  • Yang, X. H., Wu, M. H., Sun, S. F., Ding, M. W., Xie, J. L. & Xia, Q. H. (2008). J. Heterocycl. Chem.5, 1365–1369.

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