5-Meth­oxy-2-benzofuran-1(3H)-one

Paixão, D.A.; Guilardi, S.; Pereira, J.L.; Teixeira, R.R.; Arantes, J.F.

doi:10.1107/S1600536812044789

organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page o3288

doi:10.1107/S1600536812044789

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5-Methoxy-2-benzofuran-1(3H)-one

Drielly A. Paixão,^a Silvana Guilardi,^a ^* Jorge L. Pereira,^b Róbson R. Teixeira ^b ^* and Júnior F. Arantes ^b

^aInstituto de Química–UFU, Uberlândia, MG, Brazil, and ^bDepartamento de Química–UFV, Viçosa, MG, Brazil
^*Correspondence e-mail: silvana@ufu.br, robsonr.teixeira@ufv.br

(Received 16 October 2012; accepted 29 October 2012; online 7 November 2012)

In the title compound, C₉H₈O₃, the molecular skeleton is almost planar, with an r.m.s. deviation of 0.010 (2) Å. In the crystal, weak C—H⋯O hydrogen bonds connect the molecules into a two-dimensional network parallel to the ac plane.

Related literature

For the biological activity of isobenzofuran-1(3H)-one, see: Ma et al. (2012 ); Huang et al. (2012 ); Zhao et al. (2012 ); Arnone et al. (2002 ). For the synthesis, see: Zhang et al. (2009 ). For related structures, see: Sun et al. (2009 ); Mendenhall et al. (2003 ); Pereira et al. (2012 ).

Experimental

Crystal data

C₉H₈O₃
M_r = 164.15
Monoclinic, P 2₁ /c
a = 8.1819 (9) Å
b = 10.4285 (18) Å
c = 9.2965 (9) Å
β = 99.962 (8)°
V = 781.26 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.30 × 0.18 × 0.16 mm

Data collection

Enraf–Nonius KappaCCD diffractometer
14100 measured reflections
1587 independent reflections
1101 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.147
S = 1.06
1587 reflections
109 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.54	3.419 (2)	157
C8—H8A⋯O2ⁱⁱ	0.97	2.52	3.372 (2)	146
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: COLLECT (Nonius, 2000 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812044789/zs2239sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812044789/zs2239Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812044789/zs2239Isup3.cml

checkCIF report

Comment top

Isobenzofuran-1(3H)-ones (phthalides) are a class of heterocyclic compounds which occur in several natural products and have been investigated for several biological properties, such as antiplatelet (Ma et al., 2012) and antioxidant activities (Huang et al., 2012), inhibition of glutamate induced cytotoxicity in PC12 cells (Zhao et al., 2012) and phytotoxicity (Arnone et al., 2002). The title compound, C₉H₈O₃ was obtained as an intermediate in a synthetic route in the preparation of compounds endowed with phytotoxic activity and we report the crystal structure of it in a continuation of our work on the synthesis of phthalides (Pereira et al., 2012).

The title molecule (Fig. 1) is essentially planar with a mean deviation of 0.010 (2) Å from the least squares plane traced by 12 non-H atoms. All bond distances and angles agree well with those reported in the related compounds (Sun et al., 2009; Mendenhall et al., 2003; Pereira et al., 2012). In the crystal, molecules are linked via weak C6—H6···O1 hydrogen bonds (Table 1) forming chains along the ac plane. These layers are extended by C8—H8A···O2 hydrogen bonds into a two-dimensional network structure (Fig. 2).

Related literature top

For the biological activity of isobenzofuran-1(3H)-one, see: Ma et al. (2012); Huang et al. (2012); Zhao et al. (2012); Arnone et al. (2002). For the synthesis, see: Zhang et al. (2009). For related structures, see: Sun et al. (2009); Mendenhall et al. (2003); Pereira et al. (2012).

Experimental top

Starting materials were commercially available from Sigma Aldrich (USA) and were used without further purification. 5-Methoxyisobenzofuran-1(3H)-one was prepared as follows (Zhang et al., 2009). A tube of 40 ml equipped with a magnetic stir bar was charged with palladium(II) acetate (67.3 mg, 0.30 mmol), potassium bicarbonate (750 mg, 7.50 mmol), 4-methoxybenzoic acid (456 mg, 3.00 mmol) and dibromomethane (12 ml). The tube was sealed with a teflon cap and the reaction mixture was stirred at 140 °C for 18 h. After this time, the mixture was filtered through a pad of celite. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography eluted with hexane: ethyl acetate (2:1 v/v) to afford 5-methoxyisobenzofuran-1(3H)-one in 33% yield (164 mg, 1.00 mmol). The crystals suitable for X-ray crystallographic analysis were obtained by slow evaporation from acetone solution at room temperature as a yellow solid; m.p. 113.4–114.7 °C. IR (selected bands, cm^-1): 3032, 2922, 2852, 1736, 1601, 1489, 1452, 1361, 1333, 1261, 1146, 1036, 986, 773. ¹H NMR (300 MHz, CDCl₃): δ 3.89 (s, 3H, H9), 5.25 (s, 2H, H8), 6.91 (d, 1H, J = 0.6 Hz, H6), 7.02 (dd, 1H, J = 8.4, 0.6 Hz, H4), 7.80 (d, 1H, J = 8.4 Hz, H3). ¹³C NMR (75 MHz, CDCl₃): δ 56.1 (C9), 69.3 (C8), 106.2 (C6), 116.7 (C4), 118.2 (C2), 127.4 (C3), 149.6 (C7), 164.9 (C5), 171.1 (C1). HREIMS m/z (M+H⁺): Calcd for C₉H₈O₃, 165.0552; found: 165.0606.

Computing details top

Data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound, showing the atom labeling and displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title compound. Hydrogen bonds are shown as dashed lines.

5-Methoxy-2-benzofuran-1(3H)-one top

Crystal data top

C₉H₈O₃	D_x = 1.396 Mg m⁻³
M_r = 164.15	Melting point = 386.4–386.7 K
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.1819 (9) Å	Cell parameters from 1685 reflections
b = 10.4285 (18) Å	θ = 3.2–26.4°
c = 9.2965 (9) Å	µ = 0.11 mm⁻¹
β = 99.962 (8)°	T = 293 K
V = 781.26 (18) Å³	Prism, yellow
Z = 4	0.30 × 0.18 × 0.16 mm
F(000) = 344

Data collection top

Enraf–Nonius KappaCCD diffractometer	1101 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590 X-ray source	R_int = 0.049
Graphite monochromator	θ_max = 26.4°, θ_min = 3.2°
Detector resolution: 9 pixels mm^-1	h = 0→10
CCD rotation images, thick slices scans	k = 0→13
14100 measured reflections	l = −11→11
1587 independent reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0818P)² + 0.0576P] where P = (F_o² + 2F_c²)/3
1587 reflections	(Δ/σ)_max < 0.001
109 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.13 e Å⁻³

Crystal data top

C₉H₈O₃	V = 781.26 (18) Å³
M_r = 164.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1819 (9) Å	µ = 0.11 mm⁻¹
b = 10.4285 (18) Å	T = 293 K
c = 9.2965 (9) Å	0.30 × 0.18 × 0.16 mm
β = 99.962 (8)°

Data collection top

Enraf–Nonius KappaCCD diffractometer	1101 reflections with I > 2σ(I)
14100 measured reflections	R_int = 0.049
1587 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 1.06	Δρ_max = 0.16 e Å⁻³
1587 reflections	Δρ_min = −0.13 e Å⁻³
109 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
O3	0.37522 (15)	−0.24147 (11)	0.61307 (13)	0.0781 (4)
O1	0.05757 (18)	0.21719 (13)	0.30246 (15)	0.0903 (5)
C7	0.16866 (17)	0.02605 (15)	0.40441 (16)	0.0577 (4)
C5	0.32245 (19)	−0.12294 (14)	0.56458 (16)	0.0591 (4)
C3	0.3507 (2)	0.10279 (17)	0.61788 (19)	0.0691 (5)
H3	0.3971	0.17	0.6769	0.083*
C6	0.20840 (18)	−0.10008 (15)	0.43826 (16)	0.0578 (4)
H6	0.1609	−0.1669	0.3791	0.069*
O2	0.1929 (2)	0.35524 (13)	0.46580 (19)	0.1117 (6)
C4	0.39278 (19)	−0.02130 (16)	0.65283 (17)	0.0662 (4)
H4	0.4694	−0.0388	0.7367	0.079*
C2	0.2366 (2)	0.12584 (14)	0.49162 (18)	0.0631 (4)
C8	0.0518 (2)	0.07991 (17)	0.27798 (19)	0.0757 (5)
H8A	0.0874	0.0587	0.1866	0.091*
H8B	−0.0595	0.0471	0.2757	0.091*
C9	0.3066 (3)	−0.34911 (17)	0.5294 (2)	0.0956 (7)
H9A	0.3534	−0.4266	0.5748	0.143*
H9B	0.3318	−0.3432	0.4325	0.143*
H9C	0.1884	−0.3501	0.5244	0.143*
C1	0.1678 (3)	0.24532 (17)	0.4269 (2)	0.0804 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O3	0.0902 (8)	0.0618 (7)	0.0735 (7)	0.0057 (6)	−0.0102 (6)	0.0080 (5)
O1	0.1053 (10)	0.0749 (9)	0.0911 (9)	0.0277 (7)	0.0182 (8)	0.0207 (7)
C7	0.0555 (8)	0.0608 (9)	0.0574 (8)	0.0033 (6)	0.0117 (6)	0.0053 (6)
C5	0.0602 (8)	0.0573 (10)	0.0576 (8)	0.0000 (6)	0.0046 (7)	0.0042 (6)
C3	0.0743 (10)	0.0658 (10)	0.0678 (10)	−0.0129 (8)	0.0144 (8)	−0.0104 (8)
C6	0.0582 (8)	0.0576 (9)	0.0555 (8)	−0.0025 (6)	0.0038 (6)	−0.0010 (6)
O2	0.1675 (16)	0.0565 (9)	0.1221 (12)	0.0114 (8)	0.0560 (12)	0.0022 (7)
C4	0.0636 (9)	0.0742 (11)	0.0575 (8)	−0.0091 (7)	0.0008 (7)	−0.0032 (7)
C2	0.0676 (9)	0.0564 (10)	0.0687 (10)	−0.0011 (6)	0.0210 (8)	−0.0008 (7)
C8	0.0778 (11)	0.0768 (12)	0.0706 (10)	0.0153 (9)	0.0074 (8)	0.0127 (8)
C9	0.1225 (17)	0.0552 (11)	0.0988 (14)	0.0070 (10)	−0.0099 (12)	−0.0016 (9)
C1	0.1003 (14)	0.0612 (11)	0.0877 (13)	0.0118 (9)	0.0391 (11)	0.0066 (9)

Geometric parameters (Å, º) top

O3—C5	1.3603 (18)	C3—H3	0.93
O3—C9	1.425 (2)	C6—H6	0.93
O1—C1	1.370 (3)	O2—C1	1.209 (2)
O1—C8	1.449 (2)	C4—H4	0.93
C7—C2	1.376 (2)	C2—C1	1.454 (2)
C7—C6	1.378 (2)	C8—H8A	0.97
C7—C8	1.491 (2)	C8—H8B	0.97
C5—C6	1.388 (2)	C9—H9A	0.96
C5—C4	1.402 (2)	C9—H9B	0.96
C3—C4	1.364 (2)	C9—H9C	0.96
C3—C2	1.388 (2)

C5—O3—C9	117.55 (14)	C7—C2—C1	108.43 (16)
C1—O1—C8	110.05 (13)	C3—C2—C1	130.82 (16)
C2—C7—C6	122.13 (14)	O1—C8—C7	104.45 (14)
C2—C7—C8	108.56 (14)	O1—C8—H8A	110.9
C6—C7—C8	129.31 (14)	C7—C8—H8A	110.9
O3—C5—C6	124.38 (14)	O1—C8—H8B	110.9
O3—C5—C4	114.75 (14)	C7—C8—H8B	110.9
C6—C5—C4	120.87 (15)	H8A—C8—H8B	108.9
C4—C3—C2	118.08 (15)	O3—C9—H9A	109.5
C4—C3—H3	121	O3—C9—H9B	109.5
C2—C3—H3	121	H9A—C9—H9B	109.5
C7—C6—C5	117.03 (14)	O3—C9—H9C	109.5
C7—C6—H6	121.5	H9A—C9—H9C	109.5
C5—C6—H6	121.5	H9B—C9—H9C	109.5
C3—C4—C5	121.14 (15)	O2—C1—O1	120.56 (18)
C3—C4—H4	119.4	O2—C1—C2	131.0 (2)
C5—C4—H4	119.4	O1—C1—C2	108.49 (15)
C7—C2—C3	120.75 (15)

C9—O3—C5—C6	−1.0 (2)	C8—C7—C2—C1	0.17 (17)
C9—O3—C5—C4	179.11 (15)	C4—C3—C2—C7	−0.2 (2)
C2—C7—C6—C5	−0.6 (2)	C4—C3—C2—C1	179.72 (15)
C8—C7—C6—C5	−179.90 (15)	C1—O1—C8—C7	1.42 (18)
O3—C5—C6—C7	−179.79 (13)	C2—C7—C8—O1	−0.95 (16)
C4—C5—C6—C7	0.1 (2)	C6—C7—C8—O1	178.38 (14)
C2—C3—C4—C5	−0.3 (2)	C8—O1—C1—O2	178.93 (16)
O3—C5—C4—C3	−179.70 (13)	C8—O1—C1—C2	−1.36 (19)
C6—C5—C4—C3	0.4 (2)	C7—C2—C1—O2	−179.60 (18)
C6—C7—C2—C3	0.7 (2)	C3—C2—C1—O2	0.5 (3)
C8—C7—C2—C3	−179.91 (15)	C7—C2—C1—O1	0.73 (19)
C6—C7—C2—C1	−179.22 (13)	C3—C2—C1—O1	−179.17 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.54	3.419 (2)	157
C8—H8A···O2ⁱⁱ	0.97	2.52	3.372 (2)	146

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

Experimental details

Crystal data
Chemical formula	C₉H₈O₃
M_r	164.15
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.1819 (9), 10.4285 (18), 9.2965 (9)
β (°)	99.962 (8)
V (Å³)	781.26 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.30 × 0.18 × 0.16

Data collection
Diffractometer	Enraf–Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	14100, 1587, 1101
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.147, 1.06
No. of reflections	1587
No. of parameters	109
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.13

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.54	3.419 (2)	157
C8—H8A···O2ⁱⁱ	0.97	2.52	3.372 (2)	146

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

Acknowledgements

The authors thank Professor Dr Javier Ellena of the IFSC, USP, Brazil, for the X-ray data collection. This work was supported financially by CAPES, CNPq, FUNARBE and FAPEMIG. This work is also a collaboration research project of members of the Rede Mineira de Química (RQ - MG) also supported by FAPEMIG.

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