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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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536810010068/ci5047sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536810010068/ci5047Isup2.hkl
Contains datablock I

CCDC reference: 774324

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.046
  • wR factor = 0.137
  • Data-to-parameter ratio = 20.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 10
Alert level G PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature 293 K PLAT793_ALERT_4_G The Model has Chirality at C12 (Verify) .... R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 2 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 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

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.

Related literature top

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

Experimental top

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 top

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).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
3-(1,3-Benzodioxol-5-yl)-3H-benzo[f]isobenzofuran-1-one top
Crystal data top
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 top
Bruker Kappa APEXII CCD
diffractometer
4251 independent reflections
Radiation source: fine-focus sealed tube3370 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.038
ω scansθmax = 30.4°, θmin = 2.2°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1110
Tmin = 0.979, Tmax = 0.983k = 1716
19039 measured reflectionsl = 2113
Refinement top
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 = 1.02 w = 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
Crystal data top
C19H12O4V = 1414.65 (9) Å3
Mr = 304.29Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.8617 (3) ŵ = 0.10 mm1
b = 12.0417 (4) ÅT = 293 K
c = 15.0214 (5) Å0.21 × 0.19 × 0.17 mm
β = 95.848 (2)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
4251 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
3370 reflections with I > 2σ(I)
Tmin = 0.979, Tmax = 0.983Rint = 0.038
19039 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0460 restraints
wR(F2) = 0.137H-atom parameters constrained
S = 1.02Δρmax = 0.34 e Å3
4251 reflectionsΔρmin = 0.22 e Å3
208 parameters
Special details top

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) top
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)
H20.67981.16480.13970.053*
C30.7832 (2)1.02046 (14)0.16932 (9)0.0503 (4)
H30.79021.03640.22940.060*
C40.84016 (19)0.91727 (13)0.13420 (9)0.0479 (3)
H40.88420.86520.17140.057*
C50.83164 (17)0.89258 (11)0.04622 (9)0.0401 (3)
H50.87000.82390.02410.048*
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) top
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, º) top
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—C80.87 (12)
C6—C1—C2—C30.45 (19)C11—O2—C12—C13120.86 (11)
C1—C2—C3—C40.5 (2)C7—C8—C12—O2179.21 (11)
C2—C3—C4—C50.3 (2)C9—C8—C12—O21.19 (12)
C3—C4—C5—C60.0 (2)C7—C8—C12—C1361.35 (16)
C4—C5—C6—C7179.88 (12)C9—C8—C12—C13118.25 (11)
C4—C5—C6—C10.01 (18)O2—C12—C13—C14150.18 (11)
C10—C1—C6—C70.20 (16)C8—C12—C13—C1494.13 (13)
C2—C1—C6—C7179.92 (11)O2—C12—C13—C1833.93 (14)
C10—C1—C6—C5179.93 (11)C8—C12—C13—C1881.76 (13)
C2—C1—C6—C50.21 (17)C18—C13—C14—C150.74 (19)
C5—C6—C7—C8179.90 (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—C12179.39 (11)C14—C15—C16—C170.1 (2)
C7—C8—C9—C100.61 (17)C19—O4—C16—C15176.89 (14)
C12—C8—C9—C10179.03 (11)C19—O4—C16—C174.11 (15)
C7—C8—C9—C11179.26 (10)C19—O3—C17—C18176.17 (13)
C12—C8—C9—C111.10 (13)C19—O3—C17—C164.60 (15)
C8—C9—C10—C10.63 (18)C15—C16—C17—O3178.77 (12)
C11—C9—C10—C1179.21 (11)O4—C16—C17—O30.31 (15)
C2—C1—C10—C9179.49 (12)C15—C16—C17—C180.5 (2)
C6—C1—C10—C90.22 (17)O4—C16—C17—C18179.59 (12)
C12—O2—C11—O1179.35 (12)O3—C17—C18—C13178.66 (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—O1179.90 (14)C12—C13—C18—C17175.68 (10)
C10—C9—C11—O2179.59 (12)C17—O3—C19—O47.07 (15)
C8—C9—C11—O20.56 (13)C16—O4—C19—O36.88 (15)
Hydrogen-bond geometry (Å, º) top
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, y1/2, z+1/2; (ii) x+2, y+2, z.

Experimental details

Crystal data
Chemical formulaC19H12O4
Mr304.29
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.8617 (3), 12.0417 (4), 15.0214 (5)
β (°) 95.848 (2)
V3)1414.65 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.10
Crystal size (mm)0.21 × 0.19 × 0.17
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.979, 0.983
No. of measured, independent and
observed [I > 2σ(I)] reflections
19039, 4251, 3370
Rint0.038
(sin θ/λ)max1)0.711
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.046, 0.137, 1.02
No. of reflections4251
No. of parameters208
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.34, 0.22

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
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, y1/2, z+1/2; (ii) x+2, y+2, z.
 

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