6-Meth­oxyisobenzofuran-1(3H)-one

Jorge L Pereira; Róbson R Teixeira; Silvana Guilardi; Drielly A Paixão

doi:10.1107/S1600536812039074

. 2012 Sep 26;68(Pt 10):o2995. doi: 10.1107/S1600536812039074

6-Methoxyisobenzofuran-1(3H)-one

Jorge L Pereira ^a, Róbson R Teixeira ^a,^*, Silvana Guilardi ^b, Drielly A Paixão ^b

PMCID: PMC3470354 PMID: 23125767

Abstract

In the title compound, C₉H₈O₃, the molecular skeleton is almost planar [r.m.s. deviation = 0.016 (2) Å]. Weak intermolecular C—H⋯O and C—H⋯π interactions consolidate the crystal packing, with the molecules stacking in the [101] direction.

Related literature

For the biological activity of isobenzofuran-1(3H)-one, see: Brady et al. (2000 ▶); Huang et al. (2012) ▶; Cardozo et al. (2005 ▶); Yoganathan et al. (2003 ▶); Demuner et al. (2006 ▶). For related structures, see: Sun et al. (2009 ▶); Mendenhall et al. (2003 ▶).

Experimental

Crystal data

C₉H₈O₃
M _r = 164.15
Monoclinic,
a = 9.2922 (19) Å
b = 8.4982 (12) Å
c = 9.786 (2) Å
β = 90.471 (15)°
V = 772.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.28 × 0.17 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer
3304 measured reflections
1741 independent reflections
1285 reflections with I > 2σ(I)
R _int = 0.036

Refinement

R[F ² > 2σ(F ²)] = 0.050
wR(F ²) = 0.166
S = 1.12
1741 reflections
109 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.18 e Å⁻³

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 ▶).

Supplementary Material

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812039074/cv5338sup1.cif

e-68-o2995-sup1.cif^{(18KB, cif)}

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812039074/cv5338Isup2.hkl

e-68-o2995-Isup2.hkl^{(85.8KB, hkl)}

Supplementary material file. DOI: 10.1107/S1600536812039074/cv5338Isup3.cml

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

Table 1. Hydrogen-bond geometry (Å, °).

Cg1 is the centroid of C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O2ⁱ	0.96	2.55	3.490 (2)	165
C8—H8B⋯Cg1ⁱⁱ	0.97	2.84	3.637 (2)	140
C9—H9C⋯Cg1ⁱⁱⁱ	0.96	2.91	3.744 (2)	146

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Symmetry codes: (i) Inline graphic ; (ii) ; (iii) .

Acknowledgments

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 collaborative research project with members of the Rede Mineira de Química (RQ—MG), also supported by FAPEMIG.

supplementary crystallographic information

Comment

Isobenzofuran-1(3H)-one fragment, γ-lactone fused to aromatic ring, occurs in several compounds that exhibit biological activities ranging from antibacterial (Brady et al., 2000), antioxidant (Zhu et al., 2012), anticonvulsant (Cardozo et al., 2005), and anti-HIV (Yoganathan et al., 2003) to inhibition of the photosynthetic electron transport (Demuner et al., 2006). In a research program devoted to finding the phytotoxic compounds containing the isobenzofuran-1(3H)-one core, the title compound was synthesized.

The title molecule (Fig. 1) is essentially planar with a mean deviation of 0.016 (2) Å from the best plane formed by 12 non-H atoms. All bond lengths and angles are normal and correspond to those observed in the related compounds (Sun et al., 2009; Mendenhall et al., 2003). The crystal packing is stabilized by weak intermolecular C—H···O and C—H···π interactions (Table 1, Fig. 2), with a stacking direction of the molecules in [101].

Experimental

Starting materials were commercially available and were used without further purification. The synthesis of the title compound was carried out as follows. A tube of 40 ml equipped with a magnetic stir bar was charged with Palladium (II) acetate (156.8 mg, 0.70 mmol), potassium dihydrogen phosphate (3654 mg, 21.0 mmol), 3-methoxy benzoic acid (1064 mg, 7.00 mmol) and dibromomethane (28 ml). The tube was sealed with a teflon cap and the reaction mixture was stirred at 140 °C for 36 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 (hexane-ethyl acetate 2:1 v/v) to afford the title compound in 59% yield (681 mg, 4.15 mmol) as a white solid. The crystals suitable for X-ray crystallographic analysis were obtained by slow evaporation from acetone solution at room temperature. M.p. 116.9–118.4 °C. IR (selected bands, cm^-1): 3003, 2925, 2837, 1733, 1600, 1585, 1488, 1454, 1431, 1267, 1206, 1028, 973, 869, 749, 690, 545. ¹H NMR (300 MHz, MeOH-d₄) δ 3.87 (s, 3H, H-9), 5.26 (s, 2H, H-8), 7.22–7.38 (m, 3H, H-3, H-5 and H-6); ¹³C NMR (75 MHz, MeOH-d₄) δ 56.0 (C-9), 69.7 (C-8), 107.7 (C-3), 123.1; 123.3 (C-5 and C-6), 127.3 (C-2), 139.1 (C-7), 160.8 (C-4), 171.4 (C-1). HREIMS m/z (M+H⁺): Calcd for C₉H₈O₃, 165.0552; found: 165.0608.