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Acta Crystallogr Sect E Struct Rep Online. 2010 April 1; 66(Pt 4): o894.
Published online 2010 March 20. doi:  10.1107/S1600536810010068
PMCID: PMC2983915

3-(1,3-Benzodioxol-5-yl)-3H-benzo[f]isobenzofuran-1-one

Abstract

In the title compound, C19H12O4, the dioxole ring adopts a flattened envelope conformation with the methyl­ene C at the flap [deviation = 0.104 (2) Å]. The benzene ring of the benzodioxole ring system makes a dihedral angle of 76.45 (5)° with the planar [maximum deviation = 0.016 (1) Å] 3H-benzo[f]isobenzofuran-1-one ring system. In the crystal structure, the mol­ecules are linked into C(5) chains running along the b axis by inter­molecular C—H(...)O hydrogen bonds. In addition, C—H(...)π inter­actions are observed.

Related literature

For the biological activity of benzofuran compounds, see: Howlett et al. (1999 [triangle]); Twyman & Allsop (1999 [triangle]); Valerga et al. (2009 [triangle]).

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Object name is e-66-0o894-scheme1.jpg

Experimental

Crystal data

  • C19H12O4
  • M r = 304.29
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-0o894-efi1.jpg
  • a = 7.8617 (3) Å
  • b = 12.0417 (4) Å
  • c = 15.0214 (5) Å
  • β = 95.848 (2)°
  • V = 1414.65 (9) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.10 mm−1
  • T = 293 K
  • 0.21 × 0.19 × 0.17 mm

Data collection

  • Bruker Kappa APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.979, T max = 0.983
  • 19039 measured reflections
  • 4251 independent reflections
  • 3370 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.046
  • wR(F 2) = 0.137
  • S = 1.02
  • 4251 reflections
  • 208 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.22 e Å−3

Data collection: APEX2 (Bruker, 2004 [triangle]); cell refinement: SAINT (Bruker, 2004 [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: ORTEP-3 (Farrugia, 1997 [triangle]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 [triangle]).

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010068/ci5047sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010068/ci5047Isup2.hkl

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

Acknowledgments

ST and ASP thank Dr Babu Varghese, SAIF, IIT-Madras, Chennai, India, for the data collection.

supplementary crystallographic information

Comment

Molecules containing a benzofuran ring system have attracted considerable interest in view of their biological and pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999). Furan compounds exhibit antibacterial and antifungal activities (Valerga et al., 2009). Against this background and in order to obtain detailed information on molecular conformation in the solid state, an X-ray crystallographic study of the title compound has been carried out and the results are presented here.

The 3H-benzo[f]isobenzofuran-1-one ring system is essentially planar, with a maximum deviation of 0.016 (1) Å for atom C12. In the 1,3-benzodioxole ring system, the dioxole ring adopts a flattened envelope conformation with the methylene C at the flap [deviation = 0.104 (2) Å]. The benzene ring of the benzodioxole ring system makes a dihedral angle of 76.45 (5)° with the 3H-benzo[f]isobenzofuran-1-one ring system.

In the crystal structure, intermolecular C—H···O hydrogen bonds (Table 1) involving atoms C12 and O1, link the molecules into chains which run parallel to the b axis and can be described by a graph set motif of C(5). In addition, the crystal packing is stabilized by C—H···π interactions involving the C13–C18 ring.

Experimental

NaBH4 (1.6 g, 43.75 mmol) was carefully added in small portions to a solution of keto acid (3.5 g, 10.93 mmol) in THF-EtOH (2:5) at 273 K. The reaction mixture was refluxed for 12 h and then poured into ice water (200 ml). The reaction mixture was acidified using HCl (pH = 2-3) and then stirred for 0.5 h at room temperature. The solid formed was filtered and washed with methanol to afford lactone as a colourless solid.

Refinement

H atoms were positioned geometrically and allowed to ride on their parent C atoms, with C–H distances fixed in the range 0.93–0.98 Å and Uiso(H) = 1.2Ueq(C).

Figures

Fig. 1.
The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

Crystal data

C19H12O4F(000) = 632
Mr = 304.29Dx = 1.429 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 4251 reflections
a = 7.8617 (3) Åθ = 2.2–30.4°
b = 12.0417 (4) ŵ = 0.10 mm1
c = 15.0214 (5) ÅT = 293 K
β = 95.848 (2)°Block, colourless
V = 1414.65 (9) Å30.21 × 0.19 × 0.17 mm
Z = 4

Data collection

Bruker Kappa APEXII CCD diffractometer4251 independent reflections
Radiation source: fine-focus sealed tube3370 reflections with I > 2σ(I)
graphiteRint = 0.038
ω scansθmax = 30.4°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→10
Tmin = 0.979, Tmax = 0.983k = −17→16
19039 measured reflectionsl = −21→13

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)] = 0.046Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137H-atom parameters constrained
S = 1.02w = 1/[σ2(Fo2) + (0.0727P)2 + 0.2801P] where P = (Fo2 + 2Fc2)/3
4251 reflections(Δ/σ)max = 0.002
208 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = −0.22 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
O10.50740 (15)1.28238 (9)0.19129 (8)0.0587 (3)
O20.58783 (11)1.12957 (8)0.26946 (6)0.0419 (2)
O31.20824 (14)1.15928 (9)0.41662 (8)0.0588 (3)
O41.29651 (13)0.98350 (9)0.46223 (8)0.0548 (3)
C10.70723 (14)1.07497 (10)−0.02366 (7)0.0333 (2)
C20.71799 (18)1.09700 (12)−0.11570 (9)0.0443 (3)
H20.67981.1648−0.13970.053*
C30.7832 (2)1.02046 (14)−0.16932 (9)0.0503 (4)
H30.79021.0364−0.22940.060*
C40.84016 (19)0.91727 (13)−0.13420 (9)0.0479 (3)
H40.88420.8652−0.17140.057*
C50.83164 (17)0.89258 (11)−0.04622 (9)0.0401 (3)
H50.87000.8239−0.02410.048*
C60.76513 (14)0.97022 (9)0.01198 (7)0.0307 (2)
C70.75593 (14)0.94554 (9)0.10366 (7)0.0313 (2)
H70.79380.87750.12740.038*
C80.69034 (13)1.02365 (9)0.15634 (7)0.0289 (2)
C90.63280 (14)1.12596 (9)0.12091 (8)0.0324 (2)
C100.64042 (16)1.15336 (10)0.03305 (8)0.0369 (3)
H100.60231.22220.01120.044*
C110.56804 (15)1.19097 (11)0.19281 (9)0.0396 (3)
C120.66602 (15)1.02200 (10)0.25451 (7)0.0329 (2)
H120.58710.96220.26670.039*
C130.83094 (15)1.00982 (10)0.31446 (7)0.0310 (2)
C140.88263 (17)0.90475 (10)0.34263 (9)0.0389 (3)
H140.81100.84460.32800.047*
C151.04087 (17)0.88686 (11)0.39288 (9)0.0420 (3)
H151.07650.81610.41140.050*
C161.13967 (16)0.97803 (11)0.41324 (8)0.0364 (3)
C171.08753 (16)1.08282 (10)0.38590 (8)0.0355 (2)
C180.93465 (15)1.10207 (10)0.33622 (8)0.0351 (2)
H180.90131.17320.31780.042*
C191.34790 (18)1.09710 (13)0.45929 (10)0.0497 (3)
H19A1.37831.12480.51950.060*
H19B1.44681.10410.42600.060*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
O10.0624 (7)0.0454 (6)0.0653 (7)0.0244 (5)−0.0085 (5)−0.0180 (5)
O20.0383 (5)0.0475 (5)0.0398 (4)0.0108 (4)0.0030 (4)−0.0106 (4)
O30.0477 (6)0.0393 (5)0.0841 (8)−0.0062 (4)−0.0198 (5)−0.0088 (5)
O40.0438 (5)0.0521 (6)0.0637 (7)0.0030 (4)−0.0172 (5)0.0006 (5)
C10.0314 (5)0.0338 (6)0.0336 (5)−0.0029 (4)−0.0020 (4)0.0019 (4)
C20.0467 (7)0.0483 (7)0.0367 (6)−0.0045 (6)−0.0013 (5)0.0095 (5)
C30.0534 (8)0.0644 (9)0.0342 (6)−0.0127 (7)0.0097 (5)0.0010 (6)
C40.0511 (8)0.0527 (8)0.0424 (7)−0.0085 (6)0.0165 (6)−0.0114 (6)
C50.0432 (6)0.0367 (6)0.0415 (6)−0.0020 (5)0.0094 (5)−0.0059 (5)
C60.0292 (5)0.0291 (5)0.0335 (5)−0.0028 (4)0.0014 (4)−0.0027 (4)
C70.0343 (5)0.0248 (5)0.0342 (5)0.0013 (4)0.0011 (4)−0.0002 (4)
C80.0271 (5)0.0266 (5)0.0322 (5)−0.0010 (4)−0.0010 (4)−0.0023 (4)
C90.0306 (5)0.0267 (5)0.0385 (5)0.0038 (4)−0.0037 (4)−0.0043 (4)
C100.0391 (6)0.0283 (5)0.0412 (6)0.0044 (4)−0.0056 (5)0.0026 (4)
C110.0333 (6)0.0383 (6)0.0453 (6)0.0072 (5)−0.0056 (5)−0.0111 (5)
C120.0319 (5)0.0336 (6)0.0331 (5)0.0005 (4)0.0026 (4)−0.0039 (4)
C130.0328 (5)0.0335 (5)0.0270 (5)−0.0011 (4)0.0037 (4)−0.0009 (4)
C140.0402 (6)0.0319 (6)0.0440 (6)−0.0052 (5)0.0016 (5)0.0033 (5)
C150.0453 (7)0.0334 (6)0.0463 (7)0.0007 (5)−0.0004 (5)0.0083 (5)
C160.0364 (6)0.0401 (6)0.0320 (5)0.0031 (5)0.0000 (4)0.0004 (4)
C170.0372 (6)0.0325 (6)0.0363 (5)−0.0029 (4)0.0010 (4)−0.0061 (4)
C180.0385 (6)0.0290 (5)0.0373 (5)0.0011 (4)0.0005 (4)−0.0013 (4)
C190.0391 (7)0.0562 (9)0.0515 (8)−0.0040 (6)−0.0063 (6)−0.0052 (6)

Geometric parameters (Å, °)

O1—C111.1988 (15)C7—H70.93
O2—C111.3639 (17)C8—C91.3988 (15)
O2—C121.4610 (14)C8—C121.5063 (15)
O3—C171.3682 (15)C9—C101.3675 (17)
O3—C191.4260 (18)C9—C111.4665 (16)
O4—C161.3716 (15)C10—H100.93
O4—C191.4283 (18)C12—C131.5085 (16)
C1—C101.4085 (17)C12—H120.98
C1—C21.4188 (17)C13—C141.3820 (17)
C1—C61.4266 (16)C13—C181.3969 (16)
C2—C31.358 (2)C14—C151.4044 (18)
C2—H20.93C14—H140.93
C3—C41.405 (2)C15—C161.3615 (18)
C3—H30.93C15—H150.93
C4—C51.3628 (19)C16—C171.3765 (17)
C4—H40.93C17—C181.3684 (17)
C5—C61.4160 (16)C18—H180.93
C5—H50.93C19—H19A0.97
C6—C71.4178 (15)C19—H19B0.97
C7—C81.3638 (15)
C11—O2—C12111.37 (9)O1—C11—O2121.65 (12)
C17—O3—C19105.91 (11)O1—C11—C9130.04 (13)
C16—O4—C19105.73 (10)O2—C11—C9108.31 (10)
C10—C1—C2121.80 (11)O2—C12—C8103.66 (9)
C10—C1—C6119.34 (10)O2—C12—C13110.11 (9)
C2—C1—C6118.86 (11)C8—C12—C13113.49 (9)
C3—C2—C1120.96 (13)O2—C12—H12109.8
C3—C2—H2119.5C8—C12—H12109.8
C1—C2—H2119.5C13—C12—H12109.8
C2—C3—C4120.17 (12)C14—C13—C18120.66 (11)
C2—C3—H3119.9C14—C13—C12118.67 (10)
C4—C3—H3119.9C18—C13—C12120.54 (10)
C5—C4—C3120.77 (13)C13—C14—C15121.45 (12)
C5—C4—H4119.6C13—C14—H14119.3
C3—C4—H4119.6C15—C14—H14119.3
C4—C5—C6120.83 (13)C16—C15—C14116.80 (11)
C4—C5—H5119.6C16—C15—H15121.6
C6—C5—H5119.6C14—C15—H15121.6
C7—C6—C5121.33 (11)C15—C16—O4128.34 (12)
C7—C6—C1120.26 (10)C15—C16—C17121.77 (11)
C5—C6—C1118.41 (11)O4—C16—C17109.88 (11)
C8—C7—C6118.60 (10)O3—C17—C18127.62 (12)
C8—C7—H7120.7O3—C17—C16109.94 (11)
C6—C7—H7120.7C18—C17—C16122.43 (11)
C7—C8—C9120.89 (10)C17—C18—C13116.89 (11)
C7—C8—C12130.70 (10)C17—C18—H18121.6
C9—C8—C12108.41 (9)C13—C18—H18121.6
C10—C9—C8122.37 (11)O3—C19—O4108.03 (11)
C10—C9—C11129.39 (11)O3—C19—H19A110.1
C8—C9—C11108.24 (10)O4—C19—H19A110.1
C9—C10—C1118.54 (11)O3—C19—H19B110.1
C9—C10—H10120.7O4—C19—H19B110.1
C1—C10—H10120.7H19A—C19—H19B108.4
C10—C1—C2—C3179.83 (13)C11—O2—C12—C8−0.87 (12)
C6—C1—C2—C3−0.45 (19)C11—O2—C12—C13120.86 (11)
C1—C2—C3—C40.5 (2)C7—C8—C12—O2−179.21 (11)
C2—C3—C4—C5−0.3 (2)C9—C8—C12—O21.19 (12)
C3—C4—C5—C60.0 (2)C7—C8—C12—C1361.35 (16)
C4—C5—C6—C7−179.88 (12)C9—C8—C12—C13−118.25 (11)
C4—C5—C6—C1−0.01 (18)O2—C12—C13—C14150.18 (11)
C10—C1—C6—C7−0.20 (16)C8—C12—C13—C14−94.13 (13)
C2—C1—C6—C7−179.92 (11)O2—C12—C13—C18−33.93 (14)
C10—C1—C6—C5179.93 (11)C8—C12—C13—C1881.76 (13)
C2—C1—C6—C50.21 (17)C18—C13—C14—C15−0.74 (19)
C5—C6—C7—C8−179.90 (11)C12—C13—C14—C15175.14 (11)
C1—C6—C7—C80.23 (16)C13—C14—C15—C160.7 (2)
C6—C7—C8—C90.16 (16)C14—C15—C16—O4178.80 (13)
C6—C7—C8—C12−179.39 (11)C14—C15—C16—C17−0.1 (2)
C7—C8—C9—C10−0.61 (17)C19—O4—C16—C15176.89 (14)
C12—C8—C9—C10179.03 (11)C19—O4—C16—C17−4.11 (15)
C7—C8—C9—C11179.26 (10)C19—O3—C17—C18−176.17 (13)
C12—C8—C9—C11−1.10 (13)C19—O3—C17—C164.60 (15)
C8—C9—C10—C10.63 (18)C15—C16—C17—O3178.77 (12)
C11—C9—C10—C1−179.21 (11)O4—C16—C17—O3−0.31 (15)
C2—C1—C10—C9179.49 (12)C15—C16—C17—C18−0.5 (2)
C6—C1—C10—C9−0.22 (17)O4—C16—C17—C18−179.59 (12)
C12—O2—C11—O1−179.35 (12)O3—C17—C18—C13−178.66 (12)
C12—O2—C11—C90.24 (13)C16—C17—C18—C130.49 (18)
C10—C9—C11—O10.0 (2)C14—C13—C18—C170.13 (17)
C8—C9—C11—O1−179.90 (14)C12—C13—C18—C17−175.68 (10)
C10—C9—C11—O2−179.59 (12)C17—O3—C19—O4−7.07 (15)
C8—C9—C11—O20.56 (13)C16—O4—C19—O36.88 (15)

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C13–C18 ring.
D—H···AD—HH···AD···AD—H···A
C12—H12···O1i0.982.393.3277 (16)159
C3—H3···Cg1ii0.932.843.6021 (15)140

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

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: CI5047).

References

  • Bruker (2004). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J.340, 283–289. [PubMed]
  • Sheldrick, G. M. (1996). SADABS University of Gottingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2009). Acta Cryst. D65, 148–155. [PMC free article] [PubMed]
  • Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett.40, 9383–9384.
  • Valerga, P., Puerta, M. C., Rodríguez Negrín, Z., Castañedo Cancio, N. & Palma Lovillo, M. (2009). Acta Cryst. E65, o1979.

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