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Acta Crystallogr Sect E Struct Rep Online. 2008 January 1; 64(Pt 1): o137.
Published online 2007 December 6. doi:  10.1107/S160053680706326X
PMCID: PMC2915206

3-Phenyl-2-(prop-2-yn­yloxy)-1-benzofuro[3,2-d]pyrimidin-4(3H)-one

Abstract

In the title compound, C19H12N2O3, the 1-benzofuro[3,2-d]pyrimidinone unit is approximately planar, the maximum deviation from the mean plane being 0.045 (1) Å. The attached phenyl ring makes a dihedral angle of 86.73 (6)° with the fused ring system. The packing of the mol­ecules in the crystal structure is mainly governed by C—H(...)π hydrogen-bonding inter­actions.

Related literature

For related preparation and biological activity, see: Bodke & Sangapure (2003 [triangle]). For related literature, see: Ding et al., 2004 [triangle]. For the crystal structures of other fused pyrimidinone derivatives, see: Hu et al. (2005 [triangle], 2006 [triangle], 2007 [triangle]).

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Object name is e-64-0o137-scheme1.jpg

Experimental

Crystal data

  • C19H12N2O3
  • M r = 316.31
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-0o137-efi1.jpg
  • a = 12.6748 (13) Å
  • b = 7.1531 (7) Å
  • c = 17.5793 (17) Å
  • β = 104.645 (2)°
  • V = 1542.0 (3) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.09 mm−1
  • T = 292 (2) K
  • 0.30 × 0.20 × 0.06 mm

Data collection

  • Bruker SMART 4K CCD area-detector diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2003 [triangle]) T min = 0.972, T max = 0.994
  • 9340 measured reflections
  • 3496 independent reflections
  • 2681 reflections with I > 2σ(I)
  • R int = 0.041

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.119
  • S = 1.02
  • 3496 reflections
  • 217 parameters
  • H-atom parameters constrained
  • Δρmax = 0.16 e Å−3
  • Δρmin = −0.22 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680706326X/bt2655sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680706326X/bt2655Isup2.hkl

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

Acknowledgments

We gratefully acknowledge financial support of this work by the Key Science Research Project of Hubei Provincial Department of Education (No. D200724001) and the Science Research Project of Yunyang Medical College (No. 2006QDJ16).

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 one such benzofuropyrimidinone derivative. Fig. 1 shows the molecular structure of (I) with the atomic numbering scheme. Bond lengths and angles are unexceptional (Hu et al., 2005, 2006, 2007). The benzofuropyrimidine ring system is almost planar, with a maximum deviation of 0.045 (6) Å for atom C7; the C14—C19 phenyl ring is twisted with respect to it, with a dihedral angle of 86.73 (6)°. In the crystal, intermolecular C—H···π hydrogen bonds (Table 1) stabilize the crystal structure (Fig. 2).

Experimental

To a solution of ethyl 3-((phenylimino)methyleneamino)benzofuran-2-carboxylate (3 mmol) in dichloromethane (5 ml) was added sodium prop-2-yn-1-oxide (3 mmol) in prop-2-yn-1-ol (5 ml). After stirring the reaction mixture for 2 h, the solvent was removed under reduced pressure and the residue was recrystallized from ethanol to give the title compound, in a yield of 89%. Crystals suitable for single-crystal X-ray diffraction were obtained by recrystallization from a mixed solvent of ethanol and dichloromethane (1:1 v/v) at room temperature.

Refinement

All C-bound H atoms were positioned geometrically, with C—H = 0.93 Å, Uiso=1.2Ueq (C) for Csp and Csp2, C—H = 0.97 Å, Uiso = 1.2Ueq (C) for CH2.

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
The packing in the crystal structure, showing C—H···π hydrogen bonding interactions as dashed lines.

Crystal data

C19H12N2O3F000 = 656
Mr = 316.31Dx = 1.362 Mg m3
Monoclinic, P21/nMo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 3101 reflections
a = 12.6748 (13) Åθ = 2.4–27.4º
b = 7.1531 (7) ŵ = 0.09 mm1
c = 17.5793 (17) ÅT = 292 (2) K
β = 104.645 (2)ºBlock, colorless
V = 1542.0 (3) Å30.30 × 0.20 × 0.06 mm
Z = 4

Data collection

Bruker SMART 4K CCD area-detector diffractometer3496 independent reflections
Radiation source: fine-focus sealed tube2681 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.041
T = 292(2) Kθmax = 27.5º
[var phi] and ω scansθmin = 1.8º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)h = −8→16
Tmin = 0.972, Tmax = 0.994k = −9→8
9340 measured reflectionsl = −22→22

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046H-atom parameters constrained
wR(F2) = 0.119  w = 1/[σ2(Fo2) + (0.0641P)2] where P = (Fo2 + 2Fc2)/3
S = 1.02(Δ/σ)max = 0.001
3496 reflectionsΔρmax = 0.16 e Å3
217 parametersΔρmin = −0.22 e Å3
Primary atom site location: structure-invariant direct methodsExtinction correction: none

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
C11.05495 (11)0.81800 (18)0.22716 (7)0.0377 (3)
C21.11240 (12)0.85724 (19)0.30421 (8)0.0455 (4)
H21.11160.77450.34490.055*
C31.17039 (12)1.0220 (2)0.31838 (9)0.0510 (4)
H31.20991.05020.36930.061*
C41.17078 (13)1.1476 (2)0.25748 (10)0.0522 (4)
H41.20991.25840.26910.063*
C51.11500 (12)1.1122 (2)0.18077 (9)0.0482 (4)
H51.11561.19530.14020.058*
C61.05806 (11)0.9455 (2)0.16777 (7)0.0403 (3)
C70.95602 (11)0.7144 (2)0.11079 (7)0.0409 (3)
C80.98690 (11)0.66798 (18)0.18824 (7)0.0380 (3)
C90.88390 (12)0.6046 (2)0.05294 (8)0.0454 (4)
C100.88737 (11)0.40745 (19)0.16784 (7)0.0397 (3)
C110.88258 (13)0.1884 (2)0.26800 (8)0.0467 (4)
H11A0.96080.20640.28600.056*
H11B0.86780.05610.27160.056*
C120.82912 (12)0.2919 (2)0.31909 (8)0.0456 (4)
C130.78913 (15)0.3726 (2)0.36209 (10)0.0625 (5)
H130.75720.43710.39640.075*
C140.76773 (12)0.32631 (18)0.03895 (7)0.0400 (3)
C150.79825 (13)0.1850 (2)−0.00388 (8)0.0468 (4)
H150.87150.1633−0.00090.056*
C160.71813 (15)0.0755 (2)−0.05158 (9)0.0555 (4)
H160.7378−0.0211−0.08060.067*
C170.60970 (15)0.1081 (2)−0.05642 (9)0.0583 (4)
H170.55630.0355−0.08930.070*
C180.58085 (13)0.2486 (3)−0.01233 (10)0.0612 (5)
H180.50770.2693−0.01460.073*
C190.65962 (13)0.3592 (2)0.03527 (9)0.0555 (4)
H190.63990.45510.06460.067*
N10.95387 (9)0.50832 (16)0.21918 (6)0.0416 (3)
N20.85008 (9)0.44489 (16)0.08854 (6)0.0413 (3)
O10.99762 (8)0.88383 (13)0.09524 (5)0.0461 (3)
O20.85057 (11)0.63467 (16)−0.01731 (6)0.0670 (4)
O30.84625 (9)0.24665 (14)0.18664 (5)0.0495 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
C10.0361 (7)0.0393 (7)0.0367 (7)0.0037 (6)0.0071 (6)0.0010 (5)
C20.0483 (8)0.0460 (9)0.0378 (7)0.0050 (6)0.0027 (6)0.0011 (6)
C30.0485 (9)0.0527 (9)0.0455 (8)0.0006 (7)0.0003 (7)−0.0085 (7)
C40.0470 (9)0.0486 (9)0.0597 (9)−0.0061 (7)0.0112 (7)−0.0075 (7)
C50.0487 (9)0.0489 (9)0.0490 (8)−0.0044 (7)0.0161 (7)0.0043 (7)
C60.0378 (7)0.0472 (8)0.0356 (7)0.0017 (6)0.0087 (6)−0.0002 (6)
C70.0459 (8)0.0434 (8)0.0327 (7)−0.0017 (6)0.0086 (6)0.0042 (6)
C80.0382 (7)0.0410 (8)0.0331 (7)0.0049 (6)0.0055 (6)0.0014 (5)
C90.0517 (9)0.0499 (9)0.0326 (7)−0.0026 (7)0.0070 (6)0.0031 (6)
C100.0450 (8)0.0407 (7)0.0319 (7)0.0003 (6)0.0070 (6)0.0028 (6)
C110.0588 (9)0.0415 (8)0.0377 (7)0.0021 (7)0.0082 (7)0.0091 (6)
C120.0475 (9)0.0474 (9)0.0390 (8)−0.0010 (7)0.0055 (6)0.0067 (6)
C130.0673 (11)0.0661 (11)0.0560 (10)0.0056 (9)0.0194 (9)−0.0024 (8)
C140.0468 (8)0.0405 (8)0.0295 (6)0.0001 (6)0.0040 (6)0.0004 (5)
C150.0527 (9)0.0495 (9)0.0385 (7)0.0036 (7)0.0124 (7)0.0015 (6)
C160.0757 (12)0.0456 (9)0.0444 (8)0.0005 (8)0.0135 (8)−0.0092 (7)
C170.0628 (11)0.0528 (10)0.0509 (9)−0.0088 (8)−0.0011 (8)−0.0049 (7)
C180.0433 (9)0.0667 (11)0.0666 (11)0.0016 (8)0.0009 (8)−0.0073 (9)
C190.0515 (10)0.0567 (10)0.0551 (9)0.0076 (7)0.0075 (7)−0.0141 (7)
N10.0489 (7)0.0410 (7)0.0319 (6)−0.0009 (5)0.0048 (5)0.0028 (5)
N20.0475 (7)0.0443 (7)0.0290 (5)−0.0030 (5)0.0041 (5)−0.0005 (5)
O10.0533 (6)0.0497 (6)0.0342 (5)−0.0078 (5)0.0087 (4)0.0047 (4)
O20.0928 (9)0.0695 (8)0.0301 (5)−0.0207 (7)−0.0005 (5)0.0078 (5)
O30.0649 (7)0.0460 (6)0.0339 (5)−0.0101 (5)0.0058 (5)0.0040 (4)

Geometric parameters (Å, °)

C1—C61.3941 (19)C10—N21.3804 (16)
C1—C21.3946 (18)C11—O31.4486 (15)
C1—C81.4371 (18)C11—C121.457 (2)
C2—C31.378 (2)C11—H11A0.9700
C2—H20.9300C11—H11B0.9700
C3—C41.398 (2)C12—C131.164 (2)
C3—H30.9300C13—H130.9300
C4—C51.379 (2)C14—C151.3731 (19)
C4—H40.9300C14—C191.376 (2)
C5—C61.383 (2)C14—N21.4522 (17)
C5—H50.9300C15—C161.385 (2)
C6—O11.3832 (15)C15—H150.9300
C7—C81.3593 (18)C16—C171.375 (2)
C7—O11.3766 (16)C16—H160.9300
C7—C91.4200 (19)C17—C181.374 (2)
C8—N11.3749 (16)C17—H170.9300
C9—O21.2190 (16)C18—C191.378 (2)
C9—N21.4199 (18)C18—H180.9300
C10—N11.2888 (17)C19—H190.9300
C10—O31.3382 (16)
C6—C1—C2119.28 (13)O3—C11—H11A109.1
C6—C1—C8105.01 (11)C12—C11—H11A109.1
C2—C1—C8135.71 (12)O3—C11—H11B109.1
C3—C2—C1118.12 (13)C12—C11—H11B109.1
C3—C2—H2120.9H11A—C11—H11B107.9
C1—C2—H2120.9C13—C12—C11177.69 (16)
C2—C3—C4121.05 (14)C12—C13—H13180.0
C2—C3—H3119.5C15—C14—C19121.04 (13)
C4—C3—H3119.5C15—C14—N2119.98 (13)
C5—C4—C3122.07 (14)C19—C14—N2118.98 (12)
C5—C4—H4119.0C14—C15—C16118.90 (15)
C3—C4—H4119.0C14—C15—H15120.6
C4—C5—C6115.92 (13)C16—C15—H15120.6
C4—C5—H5122.0C17—C16—C15120.66 (14)
C6—C5—H5122.0C17—C16—H16119.7
C5—C6—O1124.85 (12)C15—C16—H16119.7
C5—C6—C1123.55 (12)C18—C17—C16119.57 (15)
O1—C6—C1111.59 (12)C18—C17—H17120.2
C8—C7—O1112.72 (12)C16—C17—H17120.2
C8—C7—C9123.55 (13)C17—C18—C19120.47 (16)
O1—C7—C9123.65 (12)C17—C18—H18119.8
C7—C8—N1124.03 (12)C19—C18—H18119.8
C7—C8—C1106.30 (12)C14—C19—C18119.36 (14)
N1—C8—C1129.65 (12)C14—C19—H19120.3
O2—C9—N2121.50 (13)C18—C19—H19120.3
O2—C9—C7128.57 (14)C10—N1—C8113.50 (11)
N2—C9—C7109.92 (11)C10—N2—C9122.46 (11)
N1—C10—O3122.34 (12)C10—N2—C14120.23 (11)
N1—C10—N2126.51 (13)C9—N2—C14117.18 (10)
O3—C10—N2111.15 (11)C7—O1—C6104.37 (10)
O3—C11—C12112.40 (12)C10—O3—C11116.41 (11)
C6—C1—C2—C30.0 (2)C16—C17—C18—C191.4 (3)
C8—C1—C2—C3179.90 (15)C15—C14—C19—C18−0.1 (2)
C1—C2—C3—C40.7 (2)N2—C14—C19—C18179.27 (14)
C2—C3—C4—C5−0.9 (2)C17—C18—C19—C14−0.7 (3)
C3—C4—C5—C60.4 (2)O3—C10—N1—C8179.94 (12)
C4—C5—C6—O1−179.66 (13)N2—C10—N1—C80.8 (2)
C4—C5—C6—C10.3 (2)C7—C8—N1—C10−1.97 (19)
C2—C1—C6—C5−0.5 (2)C1—C8—N1—C10176.24 (13)
C8—C1—C6—C5179.57 (13)N1—C10—N2—C91.1 (2)
C2—C1—C6—O1179.48 (12)O3—C10—N2—C9−178.16 (12)
C8—C1—C6—O1−0.48 (14)N1—C10—N2—C14−174.64 (13)
O1—C7—C8—N1178.20 (12)O3—C10—N2—C146.10 (17)
C9—C7—C8—N11.4 (2)O2—C9—N2—C10179.54 (13)
O1—C7—C8—C1−0.37 (16)C7—C9—N2—C10−1.62 (19)
C9—C7—C8—C1−177.17 (13)O2—C9—N2—C14−4.6 (2)
C6—C1—C8—C70.50 (14)C7—C9—N2—C14174.25 (12)
C2—C1—C8—C7−179.45 (15)C15—C14—N2—C10−96.71 (16)
C6—C1—C8—N1−177.95 (13)C19—C14—N2—C1083.87 (17)
C2—C1—C8—N12.1 (3)C15—C14—N2—C987.32 (15)
C8—C7—C9—O2179.20 (15)C19—C14—N2—C9−92.09 (16)
O1—C7—C9—O22.7 (3)C8—C7—O1—C60.08 (15)
C8—C7—C9—N20.5 (2)C9—C7—O1—C6176.88 (13)
O1—C7—C9—N2−176.00 (12)C5—C6—O1—C7−179.79 (13)
O3—C11—C12—C13−164 (4)C1—C6—O1—C70.26 (14)
C19—C14—C15—C160.3 (2)N1—C10—O3—C11−1.5 (2)
N2—C14—C15—C16−179.10 (12)N2—C10—O3—C11177.81 (11)
C14—C15—C16—C170.4 (2)C12—C11—O3—C1077.20 (16)
C15—C16—C17—C18−1.2 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C3—H3···Cg1i0.932.783.529 (1)138
C4—H4···Cg2ii0.932.813.641 (1)150
C11—H11A···Cg2iii0.972.763.402 (1)124
C31—H13···Cg1iv0.932.773.521 (1)139

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x+5/2, y+1/2, −z+1/2; (iii) x, y−1, z; (iv) −x+3/2, y+1/2, −z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2655).

References

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  • 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.
  • Sheldrick, G. M. (1997). SHELXL97 and SHELXS97 University of Göttingen, Germany.
  • Sheldrick, G. M. (2001). SHELXTL Version 5.0. Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (2003). SADABS Version 2.10. Bruker AXS inc., Madison, Wisconsin, USA.
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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