6-Meth­oxyisobenzofuran-1(3H)-one

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

doi:10.1107/S1600536812039074

organic compounds

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Volume 68| Part 10| October 2012| Page o2995

https://doi.org/10.1107/S1600536812039074

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6-Methoxyisobenzofuran-1(3H)-one

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

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

(Received 4 September 2012; accepted 12 September 2012; online 26 September 2012)

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, P 2₁ /c
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[F² > 2σ(F²)] = 0.050
wR(F²) = 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

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
Symmetry codes: (i) -x+1, -y, -z; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536812039074/cv5338sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812039074/cv5338Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812039074/cv5338Isup3.cml

checkCIF report

Comment top

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].

Related literature top

For the biological activity of Isobenzofuran-1(3H)-one, see: Brady et al. (2000); Zhu 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 top

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.

Structure description top

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 at the 30% probability level.
	Fig. 2. A portion of the crystal packing viewed approximately down the c axis. Dotted lines denote intermolecular C—H···O and C—H···π interactions. Centroids of six-membered rings are drawn as red balls.

6-Methoxyisobenzofuran-1(3H)-one top

Crystal data top

C₉H₈O₃	F(000) = 344
M_r = 164.15	D_x = 1.411 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.2922 (19) Å	Cell parameters from 3082 reflections
b = 8.4982 (12) Å	θ = 2.1–27.5°
c = 9.786 (2) Å	µ = 0.11 mm⁻¹
β = 90.471 (15)°	T = 293 K
V = 772.8 (2) Å³	Prism, colourless
Z = 4	0.28 × 0.17 × 0.12 mm

Data collection top

Nonius KappaCCD diffractometer	1285 reflections with I > 2σ(I)
Radiation source: Enraf Nonius FR590	R_int = 0.036
Graphite monochromator	θ_max = 27.5°, θ_min = 2.2°
Detector resolution: 9 pixels mm^-1	h = −12→12
CCD rotation images, thick slices scans	k = −10→11
3304 measured reflections	l = −12→12
1741 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.166	H-atom parameters constrained
S = 1.12	w = 1/[σ²(F_o²) + (0.0943P)² + 0.032P] where P = (F_o² + 2F_c²)/3
1741 reflections	(Δ/σ)_max < 0.001
109 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₉H₈O₃	V = 772.8 (2) Å³
M_r = 164.15	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.2922 (19) Å	µ = 0.11 mm⁻¹
b = 8.4982 (12) Å	T = 293 K
c = 9.786 (2) Å	0.28 × 0.17 × 0.12 mm
β = 90.471 (15)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.166	H-atom parameters constrained
S = 1.12	Δρ_max = 0.20 e Å⁻³
1741 reflections	Δρ_min = −0.18 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
O1	0.93834 (12)	0.04009 (14)	0.16871 (11)	0.0695 (4)
O2	0.79489 (14)	−0.11746 (14)	0.04458 (12)	0.0752 (4)
O3	0.54600 (12)	0.40633 (13)	−0.19372 (11)	0.0699 (4)
C1	0.83141 (17)	0.0134 (2)	0.07489 (15)	0.0612 (4)
C2	0.77893 (16)	0.16711 (17)	0.02593 (13)	0.0552 (4)
C3	0.67205 (15)	0.19885 (18)	−0.07089 (14)	0.0569 (4)
H3	0.6212	0.1185	−0.114	0.068*
C4	0.64497 (16)	0.35569 (18)	−0.09995 (14)	0.0568 (4)
C5	0.72174 (17)	0.47477 (18)	−0.03217 (16)	0.0632 (4)
H5	0.7013	0.5794	−0.0524	0.076*
C6	0.82660 (17)	0.44069 (19)	0.06357 (16)	0.0639 (4)
H6	0.8766	0.5208	0.108	0.077*
C7	0.85594 (16)	0.28364 (18)	0.09213 (14)	0.0572 (4)
C8	0.96195 (18)	0.2080 (2)	0.18656 (16)	0.0663 (5)
H8A	1.0596	0.2365	0.1624	0.08*
H8B	0.9448	0.2392	0.2804	0.08*
C9	0.45913 (19)	0.2893 (2)	−0.25875 (18)	0.0730 (5)
H9A	0.3942	0.3389	−0.3222	0.11*
H9B	0.4051	0.2336	−0.191	0.11*
H9C	0.5197	0.2169	−0.3067	0.11*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0805 (7)	0.0576 (7)	0.0702 (7)	0.0088 (5)	−0.0046 (5)	0.0056 (5)
O2	0.0934 (9)	0.0475 (7)	0.0847 (8)	0.0000 (5)	0.0030 (6)	0.0033 (5)
O3	0.0797 (7)	0.0492 (7)	0.0804 (7)	−0.0024 (5)	−0.0172 (6)	0.0022 (5)
C1	0.0700 (9)	0.0536 (9)	0.0602 (8)	0.0018 (7)	0.0085 (7)	0.0018 (6)
C2	0.0635 (8)	0.0479 (8)	0.0541 (7)	0.0004 (6)	0.0070 (6)	0.0000 (6)
C3	0.0651 (8)	0.0457 (8)	0.0599 (8)	−0.0047 (6)	0.0027 (6)	−0.0034 (6)
C4	0.0635 (8)	0.0480 (8)	0.0588 (8)	−0.0014 (6)	−0.0003 (6)	−0.0001 (6)
C5	0.0757 (9)	0.0428 (8)	0.0708 (9)	0.0005 (6)	−0.0035 (7)	−0.0013 (6)
C6	0.0734 (9)	0.0496 (8)	0.0686 (9)	−0.0049 (7)	−0.0032 (7)	−0.0081 (7)
C7	0.0633 (8)	0.0524 (9)	0.0561 (7)	−0.0001 (6)	0.0046 (6)	−0.0021 (6)
C8	0.0728 (9)	0.0610 (10)	0.0649 (9)	0.0037 (7)	−0.0022 (7)	−0.0042 (7)
C9	0.0790 (10)	0.0593 (10)	0.0805 (10)	−0.0097 (8)	−0.0147 (8)	0.0019 (8)

Geometric parameters (Å, º) top

O1—C1	1.366 (2)	C5—C6	1.377 (2)
O1—C8	1.454 (2)	C5—H5	0.93
O2—C1	1.199 (2)	C6—C7	1.390 (2)
O3—C4	1.3635 (19)	C6—H6	0.93
O3—C9	1.427 (2)	C7—C8	1.491 (2)
C1—C2	1.473 (2)	C8—H8A	0.97
C2—C7	1.380 (2)	C8—H8B	0.97
C2—C3	1.393 (2)	C9—H9A	0.96
C3—C4	1.385 (2)	C9—H9B	0.96
C3—H3	0.93	C9—H9C	0.96
C4—C5	1.402 (2)

C1—O1—C8	110.59 (12)	C5—C6—H6	120.8
C4—O3—C9	117.14 (13)	C7—C6—H6	120.8
O2—C1—O1	121.50 (16)	C2—C7—C6	119.63 (15)
O2—C1—C2	130.52 (17)	C2—C7—C8	108.60 (14)
O1—C1—C2	107.98 (14)	C6—C7—C8	131.77 (14)
C7—C2—C3	122.97 (15)	O1—C8—C7	104.50 (12)
C7—C2—C1	108.34 (15)	O1—C8—H8A	110.9
C3—C2—C1	128.69 (14)	C7—C8—H8A	110.9
C4—C3—C2	116.94 (14)	O1—C8—H8B	110.9
C4—C3—H3	121.5	C7—C8—H8B	110.9
C2—C3—H3	121.5	H8A—C8—H8B	108.9
O3—C4—C3	124.20 (14)	O3—C9—H9A	109.5
O3—C4—C5	115.37 (14)	O3—C9—H9B	109.5
C3—C4—C5	120.43 (15)	H9A—C9—H9B	109.5
C6—C5—C4	121.64 (15)	O3—C9—H9C	109.5
C6—C5—H5	119.2	H9A—C9—H9C	109.5
C4—C5—H5	119.2	H9B—C9—H9C	109.5
C5—C6—C7	118.38 (15)

C8—O1—C1—O2	179.83 (13)	O3—C4—C5—C6	−178.97 (12)
C8—O1—C1—C2	−0.01 (16)	C3—C4—C5—C6	0.7 (2)
O2—C1—C2—C7	−179.93 (15)	C4—C5—C6—C7	0.2 (2)
O1—C1—C2—C7	−0.11 (16)	C3—C2—C7—C6	0.6 (2)
O2—C1—C2—C3	−0.6 (3)	C1—C2—C7—C6	179.99 (12)
O1—C1—C2—C3	179.23 (12)	C3—C2—C7—C8	−179.21 (12)
C7—C2—C3—C4	0.2 (2)	C1—C2—C7—C8	0.18 (16)
C1—C2—C3—C4	−179.01 (12)	C5—C6—C7—C2	−0.8 (2)
C9—O3—C4—C3	4.2 (2)	C5—C6—C7—C8	178.95 (14)
C9—O3—C4—C5	−176.13 (13)	C1—O1—C8—C7	0.11 (15)
C2—C3—C4—O3	178.74 (12)	C2—C7—C8—O1	−0.18 (15)
C2—C3—C4—C5	−0.9 (2)	C6—C7—C8—O1	−179.96 (14)

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x+1, −y, −z; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, 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)	9.2922 (19), 8.4982 (12), 9.786 (2)
β (°)	90.471 (15)
V (Å³)	772.8 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.28 × 0.17 × 0.12

Data collection
Diffractometer	Nonius KappaCCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3304, 1741, 1285
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.166, 1.12
No. of reflections	1741
No. of parameters	109
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.18

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

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)	164.9
C8—H8B···Cg1ⁱⁱ	0.97	2.84	3.637 (2)	140.0
C9—H9C···Cg1ⁱⁱⁱ	0.96	2.91	3.744 (2)	146.0

Symmetry codes: (i) −x+1, −y, −z; (ii) x, −y+3/2, z−1/2; (iii) x, −y+3/2, 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 collaborative research project with members of the Rede Mineira de Química (RQ—MG), also supported by FAPEMIG.

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