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Acta Crystallogr Sect E Struct Rep Online. 2009 November 1; 65(Pt 11): o2839.
Published online 2009 October 23. doi:  10.1107/S1600536809042925
PMCID: PMC2971295

3-Isopropyl-2-(4-methoxy­phen­oxy)-1-benzo­furo[3,2-d]pyrimidin-4(3H)-one

Abstract

In the title compound, C20H18N2O4, all non-H atoms of the three fused rings of the benzofuro[3,2-d]pyrimidine system are almost coplanar (r.m.s. deviation 0.021 Å). The dihedral angle between the fused ring system and the benzene ring is 1.47 (12)°. Intra­molecular and inter­molecular C—H(...)O hydrogen bonds together with weak C—H(...)π inter­actions stabilize the structure.

Related literature

For the biological activity of benzofuropyrimidine derivatives, see: Bodke & Sangapure (2003 [triangle]). For the synthesis of the title compound, see: Ding et al. (2004 [triangle]). For the structures of other fused pyrimidinone derivatives, see: Hu et al. (2005 [triangle], 2006 [triangle], 2007 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-o2839-scheme1.jpg

Experimental

Crystal data

  • C20H18N2O4
  • M r = 350.36
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-o2839-efi1.jpg
  • a = 10.0358 (7) Å
  • b = 14.2879 (10) Å
  • c = 13.2071 (9) Å
  • β = 112.089 (1)°
  • V = 1754.8 (2) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 298 K
  • 0.26 × 0.13 × 0.10 mm

Data collection

  • Bruker SMART CCD area-detector diffractometer
  • Absorption correction: none
  • 11156 measured reflections
  • 3809 independent reflections
  • 3354 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.070
  • wR(F 2) = 0.155
  • S = 1.22
  • 3809 reflections
  • 238 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.23 e Å−3

Data collection: SMART (Bruker, 2001 [triangle]); cell refinement: SAINT (Bruker, 2001 [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: PLATON (Spek, 2009 [triangle]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809042925/bt5104sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042925/bt5104Isup2.hkl

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

Acknowledgments

The authors gratefully acknowledge financial support of this work by Yunyang Medical College (grant No. 2007ZQB24).

supplementary crystallographic information

Comment

Benzofuropyrimidine derivatives are of interest as possible antiviral agents, and because of their other biological properties, including antibacterial, antifungal, antiallergic and antiinflammatory activities (Bodke & Sangapure, 2003). We have recently focused on the synthesis of the fused heterocyclic systems containing pyrimidinone via aza-Wittig reactions at room temperature (Ding et al., 2004). We present here the structure of such a benzofuropyrimidinone derivative. Fig. 1 shows the molecular structure of the title compound with the atomic numbering scheme. Intramolecular C—H···O and intermolecular C—H···O hydrogen bonds together with weak C—H···π interactions (Table 1) stabilize the structure. (Fig.2).

Experimental

To a solution of N-(2-ethoxycarbonylbenzofuran-3-yl)iminotriphenylphosphorane (3 mmol) in dry dichloromethane (15 ml) was added isopropyl isocyanate (3 mmol) under nitrogen at room temperature. After the reaction mixture had been allowed to stand for 20 h at 273–278 K, the solvent was removed under reduced pressure and diethyl ether-petroleum ether (1:2 v/v, 20 ml) was added to precipitate the triphenylphosphine oxide. After filtration, the solvent was removed to give the ethyl 3-((isopropylimino)methyleneamino)-2,3-dihydrobenzofuran-2-carboxylate, which was used directly without further purification. To a solution of ethyl 3-((isopropylimino)methyleneamino)-2,3- dihydrobenzofuran-2-carboxylate in acetonitrile (15 ml) were added 4-methylphenol (3 mmol) and anhydrous K2CO3 (1 mmol). The mixture was stirred for 6 h at 313–323 K. The solution was concentrated under reduced pressure and the residue was recrystallized from dichloromethane and ethanol (1:2 v/v) to give the title compound. Suitable crystals were obtained by vapour diffusion of ethanol into dichloromethane at room temperature.

Refinement

H atoms were placed at calculated positions, with C—H distances of 0.97 and 0.93Å for H atoms bonded to sp3 and sp2 C atoms, respectively. They were refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Figures

Fig. 1.
View of the molecular structure of (I), showing the atom labelling schemeand with displacement ellipsoids drawn at the 50% probability level.
Fig. 2.
A partial view of the crystal packing of (I), showing the formation of C—H···O hydrogen-bonded. showing as dashed lines.

Crystal data

C20H18N2O4F(000) = 736
Mr = 350.36Dx = 1.326 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 10.0358 (7) ÅCell parameters from 4035 reflections
b = 14.2879 (10) Åθ = 2.2–27.2°
c = 13.2071 (9) ŵ = 0.09 mm1
β = 112.089 (1)°T = 298 K
V = 1754.8 (2) Å3Block, colorless
Z = 40.26 × 0.13 × 0.10 mm

Data collection

Bruker SMART CCD area-detector diffractometer3354 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.040
graphiteθmax = 27.0°, θmin = 2.2°
phi and ω scansh = −12→12
11156 measured reflectionsk = −14→18
3809 independent reflectionsl = −16→16

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.070Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-atom parameters constrained
S = 1.22w = 1/[σ2(Fo2) + (0.0482P)2 + 0.6117P] where P = (Fo2 + 2Fc2)/3
3809 reflections(Δ/σ)max < 0.001
238 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

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)

xyzUiso*/Ueq
C10.7439 (2)0.49152 (15)0.08888 (16)0.0449 (5)
C20.8316 (3)0.53714 (18)0.04468 (19)0.0556 (6)
H20.89980.50430.02680.067*
C30.8149 (3)0.63207 (19)0.0280 (2)0.0665 (7)
H30.87250.6640−0.00160.080*
C40.7126 (3)0.68112 (18)0.0549 (2)0.0649 (7)
H40.70230.74510.04130.078*
C50.6270 (3)0.63811 (17)0.1005 (2)0.0588 (6)
H50.56000.67130.11940.071*
C60.6450 (2)0.54273 (16)0.11700 (17)0.0484 (5)
C70.6210 (2)0.39759 (16)0.15826 (17)0.0453 (5)
C80.7248 (2)0.39635 (15)0.11576 (16)0.0428 (5)
C90.7502 (2)0.24186 (15)0.13723 (17)0.0440 (5)
C100.5734 (2)0.31676 (17)0.19732 (17)0.0480 (5)
C110.6003 (2)0.14330 (17)0.21223 (19)0.0523 (6)
H110.51800.15700.23250.063*
C120.5457 (3)0.0739 (2)0.1184 (2)0.0671 (7)
H12A0.47820.10440.05520.101*
H12B0.49940.02260.13890.101*
H12C0.62510.05080.10190.101*
C130.7157 (3)0.10533 (19)0.3141 (2)0.0654 (7)
H13A0.80000.09100.29920.098*
H13B0.68150.04950.33690.098*
H13C0.73900.15130.37120.098*
C140.9024 (2)0.14978 (15)0.07749 (18)0.0448 (5)
C150.8475 (2)0.14131 (19)−0.0328 (2)0.0605 (6)
H150.74900.1470−0.07140.073*
C160.9378 (2)0.12422 (18)−0.08780 (19)0.0567 (6)
H160.90020.1187−0.16350.068*
C171.0832 (2)0.11536 (14)−0.03082 (18)0.0438 (5)
C181.1364 (2)0.12380 (19)0.08137 (19)0.0601 (6)
H181.23470.11770.12070.072*
C191.0466 (2)0.14111 (19)0.13570 (19)0.0574 (6)
H191.08340.14690.21140.069*
C201.1334 (3)0.1004 (2)−0.1929 (2)0.0735 (8)
H20A1.06740.0498−0.22340.110*
H20B1.21430.0941−0.21440.110*
H20C1.08590.1589−0.21920.110*
N10.79382 (18)0.31642 (13)0.10474 (14)0.0452 (4)
N20.64378 (18)0.23540 (13)0.17913 (14)0.0456 (4)
O10.56950 (16)0.48638 (11)0.16127 (13)0.0528 (4)
O20.48616 (19)0.31249 (13)0.24071 (16)0.0677 (5)
O30.80979 (17)0.15842 (11)0.13495 (14)0.0561 (4)
O41.18117 (17)0.09783 (12)−0.07769 (13)0.0584 (4)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0430 (11)0.0496 (12)0.0382 (11)−0.0016 (9)0.0107 (9)−0.0053 (9)
C20.0547 (13)0.0561 (15)0.0600 (14)−0.0039 (11)0.0262 (11)−0.0047 (11)
C30.0730 (17)0.0602 (16)0.0691 (17)−0.0135 (13)0.0298 (14)−0.0014 (13)
C40.0740 (17)0.0493 (14)0.0637 (16)−0.0016 (12)0.0171 (13)−0.0009 (12)
C50.0604 (14)0.0517 (14)0.0591 (15)0.0087 (11)0.0165 (12)−0.0055 (11)
C60.0458 (11)0.0535 (13)0.0413 (11)0.0041 (10)0.0112 (9)−0.0028 (9)
C70.0404 (11)0.0526 (13)0.0428 (11)0.0062 (9)0.0154 (9)−0.0020 (9)
C80.0387 (10)0.0508 (12)0.0369 (10)0.0011 (9)0.0121 (8)−0.0028 (9)
C90.0417 (11)0.0494 (12)0.0416 (11)0.0044 (9)0.0165 (9)0.0009 (9)
C100.0412 (11)0.0598 (14)0.0440 (12)0.0039 (10)0.0172 (9)−0.0007 (10)
C110.0488 (12)0.0560 (14)0.0592 (14)−0.0052 (10)0.0283 (11)0.0011 (11)
C120.0556 (14)0.0657 (16)0.0727 (17)−0.0083 (12)0.0159 (13)−0.0067 (13)
C130.0754 (17)0.0685 (17)0.0530 (14)−0.0054 (13)0.0250 (13)0.0105 (12)
C140.0465 (11)0.0387 (11)0.0533 (13)0.0051 (9)0.0236 (10)0.0039 (9)
C150.0395 (11)0.0805 (18)0.0561 (15)0.0139 (11)0.0118 (10)0.0019 (12)
C160.0485 (12)0.0753 (17)0.0423 (12)0.0080 (11)0.0126 (10)−0.0022 (11)
C170.0438 (11)0.0368 (11)0.0532 (12)0.0047 (8)0.0210 (9)0.0034 (9)
C180.0355 (11)0.0880 (19)0.0519 (14)0.0053 (11)0.0109 (10)0.0042 (12)
C190.0516 (13)0.0754 (17)0.0435 (12)0.0023 (12)0.0158 (10)0.0002 (11)
C200.0799 (18)0.088 (2)0.0628 (17)0.0156 (15)0.0391 (15)−0.0024 (14)
N10.0425 (9)0.0485 (10)0.0489 (10)0.0028 (8)0.0220 (8)−0.0005 (8)
N20.0415 (9)0.0539 (11)0.0432 (10)−0.0009 (8)0.0179 (8)0.0001 (8)
O10.0511 (9)0.0542 (9)0.0589 (10)0.0086 (7)0.0272 (8)−0.0022 (7)
O20.0671 (11)0.0722 (12)0.0841 (12)0.0062 (9)0.0517 (10)0.0032 (9)
O30.0616 (10)0.0494 (9)0.0714 (11)0.0106 (7)0.0411 (8)0.0114 (8)
O40.0529 (9)0.0666 (11)0.0617 (10)0.0120 (8)0.0285 (8)0.0043 (8)

Geometric parameters (Å, °)

C1—C21.388 (3)C11—H110.9800
C1—C61.392 (3)C12—H12A0.9600
C1—C81.436 (3)C12—H12B0.9600
C2—C31.374 (4)C12—H12C0.9600
C2—H20.9300C13—H13A0.9600
C3—C41.395 (4)C13—H13B0.9600
C3—H30.9300C13—H13C0.9600
C4—C51.367 (4)C14—C151.355 (3)
C4—H40.9300C14—C191.365 (3)
C5—C61.381 (3)C14—O31.409 (2)
C5—H50.9300C15—C161.380 (3)
C6—O11.377 (3)C15—H150.9300
C7—C81.357 (3)C16—C171.373 (3)
C7—O11.376 (3)C16—H160.9300
C7—C101.418 (3)C17—O41.368 (2)
C8—N11.372 (3)C17—C181.378 (3)
C9—N11.285 (3)C18—C191.369 (3)
C9—O31.339 (3)C18—H180.9300
C9—N21.378 (3)C19—H190.9300
C10—O21.215 (3)C20—O41.414 (3)
C10—N21.427 (3)C20—H20A0.9600
C11—N21.502 (3)C20—H20B0.9600
C11—C131.508 (3)C20—H20C0.9600
C11—C121.519 (3)
C2—C1—C6119.6 (2)H12A—C12—H12C109.5
C2—C1—C8135.5 (2)H12B—C12—H12C109.5
C6—C1—C8104.85 (19)C11—C13—H13A109.5
C3—C2—C1118.2 (2)C11—C13—H13B109.5
C3—C2—H2120.9H13A—C13—H13B109.5
C1—C2—H2120.9C11—C13—H13C109.5
C2—C3—C4120.8 (2)H13A—C13—H13C109.5
C2—C3—H3119.6H13B—C13—H13C109.5
C4—C3—H3119.6C15—C14—C19120.9 (2)
C5—C4—C3122.1 (2)C15—C14—O3120.16 (19)
C5—C4—H4119.0C19—C14—O3118.6 (2)
C3—C4—H4119.0C14—C15—C16120.0 (2)
C4—C5—C6116.5 (2)C14—C15—H15120.0
C4—C5—H5121.7C16—C15—H15120.0
C6—C5—H5121.7C17—C16—C15120.0 (2)
O1—C6—C5125.7 (2)C17—C16—H16120.0
O1—C6—C1111.57 (19)C15—C16—H16120.0
C5—C6—C1122.7 (2)O4—C17—C16124.4 (2)
C8—C7—O1112.26 (19)O4—C17—C18116.66 (19)
C8—C7—C10123.7 (2)C16—C17—C18118.9 (2)
O1—C7—C10123.99 (18)C19—C18—C17120.9 (2)
C7—C8—N1123.5 (2)C19—C18—H18119.5
C7—C8—C1106.56 (19)C17—C18—H18119.5
N1—C8—C1129.93 (18)C14—C19—C18119.2 (2)
N1—C9—O3121.27 (18)C14—C19—H19120.4
N1—C9—N2127.03 (19)C18—C19—H19120.4
O3—C9—N2111.69 (18)O4—C20—H20A109.5
O2—C10—C7127.8 (2)O4—C20—H20B109.5
O2—C10—N2121.9 (2)H20A—C20—H20B109.5
C7—C10—N2110.30 (17)O4—C20—H20C109.5
N2—C11—C13111.44 (18)H20A—C20—H20C109.5
N2—C11—C12112.94 (19)H20B—C20—H20C109.5
C13—C11—C12114.4 (2)C9—N1—C8113.92 (17)
N2—C11—H11105.7C9—N2—C10121.34 (18)
C13—C11—H11105.7C9—N2—C11121.94 (18)
C12—C11—H11105.7C10—N2—C11116.67 (17)
C11—C12—H12A109.5C7—O1—C6104.74 (16)
C11—C12—H12B109.5C9—O3—C14118.74 (16)
H12A—C12—H12B109.5C17—O4—C20118.16 (19)
C11—C12—H12C109.5
C6—C1—C2—C3−1.4 (3)C15—C14—C19—C180.1 (4)
C8—C1—C2—C3178.1 (2)O3—C14—C19—C18173.9 (2)
C1—C2—C3—C40.0 (4)C17—C18—C19—C140.2 (4)
C2—C3—C4—C51.3 (4)O3—C9—N1—C8−177.98 (18)
C3—C4—C5—C6−1.1 (4)N2—C9—N1—C80.8 (3)
C4—C5—C6—O1−179.7 (2)C7—C8—N1—C90.8 (3)
C4—C5—C6—C1−0.3 (3)C1—C8—N1—C9179.9 (2)
C2—C1—C6—O1−178.92 (19)N1—C9—N2—C10−3.9 (3)
C8—C1—C6—O11.4 (2)O3—C9—N2—C10174.94 (17)
C2—C1—C6—C51.6 (3)N1—C9—N2—C11178.7 (2)
C8—C1—C6—C5−178.1 (2)O3—C9—N2—C11−2.5 (3)
O1—C7—C8—N1179.51 (18)O2—C10—N2—C9−175.2 (2)
C10—C7—C8—N10.8 (3)C7—C10—N2—C94.8 (3)
O1—C7—C8—C10.2 (2)O2—C10—N2—C112.4 (3)
C10—C7—C8—C1−178.48 (19)C7—C10—N2—C11−177.66 (17)
C2—C1—C8—C7179.5 (2)C13—C11—N2—C970.7 (3)
C6—C1—C8—C7−1.0 (2)C12—C11—N2—C9−59.8 (3)
C2—C1—C8—N10.2 (4)C13—C11—N2—C10−106.9 (2)
C6—C1—C8—N1179.8 (2)C12—C11—N2—C10122.7 (2)
C8—C7—C10—O2176.5 (2)C8—C7—O1—C60.7 (2)
O1—C7—C10—O2−2.0 (4)C10—C7—O1—C6179.3 (2)
C8—C7—C10—N2−3.5 (3)C5—C6—O1—C7178.2 (2)
O1—C7—C10—N2177.99 (18)C1—C6—O1—C7−1.3 (2)
C19—C14—C15—C16−0.4 (4)N1—C9—O3—C14−11.9 (3)
O3—C14—C15—C16−174.0 (2)N2—C9—O3—C14169.19 (17)
C14—C15—C16—C170.3 (4)C15—C14—O3—C9−79.2 (3)
C15—C16—C17—O4179.5 (2)C19—C14—O3—C9107.1 (2)
C15—C16—C17—C180.0 (4)C16—C17—O4—C208.2 (3)
O4—C17—C18—C19−179.8 (2)C18—C17—O4—C20−172.2 (2)
C16—C17—C18—C19−0.3 (4)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C4—H4···O4i0.932.493.311 (3)147
C11—H11···O20.982.252.761 (3)111
C12—H12C···O30.962.322.845 (4)114
C13—H13A···O30.962.412.957 (3)116
C16—H16···Cg2ii0.932.763.551 (2)143
C19—H19···Cg3iii0.932.903.742 (3)152

Symmetry codes: (i) −x+2, −y+1, −z; (ii) x, −y−1/2, z−3/2; (iii) −x+2, y−1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5104).

References

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  • Bruker (2001). SMART and SAINT-Plus Bruker AXS Inc., Madison, Wisconsin, USA.
  • Ding, M. W., Xu, S. Z. & Zhao, J. F. (2004). J. Org. Chem.69, 8366–8371. [PubMed]
  • Hu, Y.-G., Li, G.-H., Tian, J.-H., Ding, M.-W. & He, H.-W. (2005). Acta Cryst. E61, o3266–o3268.
  • Hu, Y.-G., Li, G.-H. & Zhou, M.-H. (2007). Acta Cryst. E63, o1836–o1838.
  • Hu, Y.-G., Zheng, A.-H. & Li, G.-H. (2006). Acta Cryst. E62, o1457–o1459.
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  • Spek, A. L. (2009). Acta Cryst D65, 148–155. [PMC free article] [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography