Methyl 2-(5-bromo-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536808037768

organic compounds

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ISSN: 2056-9890

Volume 64| Part 12| December 2008| Page o2397

doi:10.1107/S1600536808037768

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Methyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong, Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
^*Correspondence e-mail: uklee@pknu.ac.kr

(Received 30 October 2008; accepted 14 November 2008; online 20 November 2008)

The title compound, C₁₂H₁₁BrO₄S, was synthesized by the oxidation of methyl 2-(5-bromo-3-methylsulfanyl-1-benzofuran-2-yl)acetate with 3-chloroperoxybenzoic acid. The O atom and the methyl group of the methylsulfinyl substituent lie on opposite sides of the plane of the benzofuran ring system. The crystal structure is stabilized by C—H⋯π interactions, involving a methyl H atom and the benzene ring of a neighbouring molecule, and by weak intermolecular C—H⋯O hydrogen bonds.

Related literature

For the crystal structures of similar methyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives, see: Choi et al. (2008a ,b ).

Experimental

Crystal data

C₁₂H₁₁BrO₄S
M_r = 331.18
Triclinic, $[P \overline 1]$
a = 7.9696 (5) Å
b = 9.1146 (6) Å
c = 10.3100 (7) Å
α = 72.587 (1)°
β = 78.716 (1)°
γ = 69.082 (1)°
V = 664.17 (8) Å³
Z = 2
Mo Kα radiation
μ = 3.25 mm⁻¹
T = 298 (2) K
0.40 × 0.30 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ) T_min = 0.327, T_max = 0.530
3786 measured reflections
2560 independent reflections
2084 reflections with I > 2σ(I)
R_int = 0.015

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.099
S = 0.98
2560 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.80 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the benzene ring C2–C7.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O2ⁱ	0.93	2.43	3.334 (4)	163
C9—H9B⋯O1ⁱⁱ	0.97	2.59	3.555 (3)	171
C9—H9A⋯O2ⁱⁱⁱ	0.97	2.22	3.177 (4)	169
C12—H12B⋯Cg^iv	0.96	2.99	3.903 (4)	159
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z+1; (iii) -x+2, -y+1, -z; (iv) x, y+1, z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablock I. DOI: 10.1107/S1600536808037768/su2077sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808037768/su2077Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing research on the synthesis and structure of methyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate analogues, the crystal structure of methyl 2-(5-methyl-3-methylsulfinyl-1-benzofuran-2-yl)acetate (Choi et al., 2008a) and methyl 2-(5-chloro-3-methylsulfinyl-1-benzofuran-2-yl) acetate (Choi et al., 2008b) have been reported. Here we describe the crystal structure of the title compound (I), synthesized by the oxidation of methyl 2-(5-bromo-3-methylsulfanyl-1-benzofuran-2-yl)acetate with 3-chloroperoxybenzoic acid.

The molecular structure of compound (I) is illustrated in Fig. 1. The benzofuran unit is essentially planar, with a mean deviation of 0.013 (2) Å from the least-squares plane defined by the nine constituent atoms.

The crystal packing of compound (I) (see Fig. 2) is stabilized by intermolecular C—H···π interactions between an H-atom of the C12-methyl group and the benzene ring of the benzofuran fragment, with a C12—H12B···Cg^iv separation of 3.903 (4) Å (Fig. 2 and Table 1; Cg is the centroid of benzene ring C2–C7, symmetry codes as in Fig. 2). In addition, the molecular packing exhibits three intermolecular C—H···O hydrogen bonds (Fig. 2 & Table 1).

Related literature top

For the crystal structures of similar methyl 2-(3-methylsulfinyl-1-benzofuran-2-yl)acetate derivatives, see: Choi et al. (2008a,b).

Experimental top

77% 3-Chloroperoxybenzoic acid (190 mg, 0.85 mmol) was added in small portions to a stirred solution of methyl 2-(5-bromo-3-methylsulfanyl-1-benzofuran-2-yl)acetate (252 mg, 0.8 mmol) in dichloromethane (30 ml) at 273 K. After stirring for 3 h at rt, the mixture was washed with a saturated sodium bicarbonate solution and the organic layer was separated, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography (hexane-ethyl acetate 1:2, v/v) to afford compound (I) as a colorless solid [yield 86%, m.p. 405–406 K; R_f = 0.45 (hexane-ethyl acetate, 1:2, v/v)]. Single crystals, suitable for X-ray analysis, were prepared by evaporation of a solution of compound (I) in benzene at rt. Spectroscopic analysis: ¹H NMR (CDCl₃, 400 MHz) δ 3.06 (s, 3H), 3.75 (s, 3H), 4.04 (s, 2H), 7.34–7.53 (m, 2H), 7.44 (d, J = 8.80 Hz, 1H), 8.07 (d, J = 1.84 Hz, 1H); EI—MS 332 [M+2], 330[M⁺].

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of compound (I), showing the atom numbering scheme and displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A view of the crystal packing of compound (I), showing the C—H···π and C—H···O interactions as dotted lines. Cg denotes the ring centroid. [Symmetry codes: (i) -x + 1, -y + 1, -zz; (ii) -x + 2, -y + 1, -z + 1; (iii) -x + 2, -y + 1, -z; (iv) x, y + 1, z; (v) -x + 2, -y + 1, -z; (vi) -x + 1, -y + 1, -z.]

Methyl 2-(5-bromo-3-methylsulfinyl-1-benzofuran-2-yl)acetate top

Crystal data top

C₁₂H₁₁BrO₄S	Z = 2
M_r = 331.18	F(000) = 332
Triclinic, P1	D_x = 1.656 Mg m⁻³
Hall symbol: -P 1	Melting point = 405–406 K
a = 7.9696 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.1146 (6) Å	Cell parameters from 1892 reflections
c = 10.3100 (7) Å	θ = 2.1–27.8°
α = 72.587 (1)°	µ = 3.25 mm⁻¹
β = 78.716 (1)°	T = 298 K
γ = 69.082 (1)°	Block, colourless
V = 664.17 (8) Å³	0.40 × 0.30 × 0.20 mm

Data collection top

Bruker SMART CCD diffractometer	2560 independent reflections
Radiation source: fine-focus sealed tube	2084 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
Detector resolution: 10.0 pixels mm^-1	θ_max = 26.0°, θ_min = 2.5°
ϕ and ω scans	h = −9→5
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −11→11
T_min = 0.327, T_max = 0.530	l = −12→12
3786 measured 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.099	H-atom parameters constrained
S = 0.98	w = 1/[σ²(F_o²) + (0.0506P)² + 0.5362P] where P = (F_o² + 2F_c²)/3
2560 reflections	(Δ/σ)_max = 0.001
164 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.80 e Å⁻³

Crystal data top

C₁₂H₁₁BrO₄S	γ = 69.082 (1)°
M_r = 331.18	V = 664.17 (8) Å³
Triclinic, P1	Z = 2
a = 7.9696 (5) Å	Mo Kα radiation
b = 9.1146 (6) Å	µ = 3.25 mm⁻¹
c = 10.3100 (7) Å	T = 298 K
α = 72.587 (1)°	0.40 × 0.30 × 0.20 mm
β = 78.716 (1)°

Data collection top

Bruker SMART CCD diffractometer	2560 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	2084 reflections with I > 2σ(I)
T_min = 0.327, T_max = 0.530	R_int = 0.015
3786 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	0 restraints
wR(F²) = 0.099	H-atom parameters constrained
S = 0.98	Δρ_max = 0.35 e Å⁻³
2560 reflections	Δρ_min = −0.80 e Å⁻³
164 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
Br	0.26775 (5)	0.20066 (4)	0.38327 (5)	0.07396 (18)
S	0.73771 (11)	0.63026 (10)	0.03527 (7)	0.0505 (2)
O1	0.8367 (3)	0.4636 (2)	0.42105 (19)	0.0450 (5)
O2	0.7437 (4)	0.4993 (3)	−0.0262 (2)	0.0668 (7)
O3	1.0188 (3)	0.8974 (3)	0.2240 (3)	0.0718 (7)
O4	0.7513 (3)	0.8989 (3)	0.1905 (3)	0.0724 (7)
C1	0.7429 (4)	0.5435 (3)	0.2117 (3)	0.0422 (6)
C2	0.6455 (4)	0.4363 (3)	0.2987 (3)	0.0408 (6)
C3	0.5121 (4)	0.3798 (3)	0.2824 (3)	0.0466 (7)
H3	0.4651	0.4089	0.1993	0.056*
C4	0.4537 (4)	0.2784 (4)	0.3965 (4)	0.0510 (7)
C5	0.5227 (5)	0.2305 (4)	0.5228 (4)	0.0550 (8)
H5	0.4796	0.1604	0.5964	0.066*
C6	0.6542 (4)	0.2870 (4)	0.5381 (3)	0.0526 (8)
H6	0.7023	0.2566	0.6210	0.063*
C7	0.7117 (4)	0.3904 (3)	0.4254 (3)	0.0419 (6)
C8	0.8535 (4)	0.5552 (3)	0.2893 (3)	0.0413 (6)
C9	0.9848 (4)	0.6447 (4)	0.2609 (3)	0.0473 (7)
H9A	1.0742	0.6117	0.1877	0.057*
H9B	1.0470	0.6145	0.3416	0.057*
C10	0.9012 (4)	0.8259 (4)	0.2215 (3)	0.0483 (7)
C11	0.5088 (5)	0.7628 (4)	0.0366 (4)	0.0637 (9)
H11A	0.4834	0.8234	−0.0551	0.096*
H11B	0.4918	0.8363	0.0916	0.096*
H11C	0.4285	0.6997	0.0740	0.096*
C12	0.9545 (7)	1.0738 (5)	0.1880 (7)	0.1065 (18)
H12A	1.0493	1.1133	0.1927	0.160*
H12B	0.8527	1.1114	0.2506	0.160*
H12C	0.9191	1.1131	0.0968	0.160*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br	0.0572 (2)	0.0513 (2)	0.1163 (4)	−0.02436 (17)	−0.0138 (2)	−0.0133 (2)
S	0.0535 (5)	0.0626 (5)	0.0392 (4)	−0.0239 (4)	−0.0121 (3)	−0.0067 (3)
O1	0.0450 (11)	0.0494 (11)	0.0411 (10)	−0.0113 (9)	−0.0157 (9)	−0.0094 (9)
O2	0.0746 (17)	0.0842 (17)	0.0506 (13)	−0.0229 (14)	−0.0132 (12)	−0.0286 (12)
O3	0.0615 (15)	0.0579 (14)	0.108 (2)	−0.0253 (12)	−0.0235 (14)	−0.0201 (14)
O4	0.0561 (15)	0.0537 (14)	0.103 (2)	−0.0180 (12)	−0.0308 (14)	0.0016 (13)
C1	0.0433 (15)	0.0454 (15)	0.0412 (14)	−0.0144 (13)	−0.0090 (12)	−0.0122 (12)
C2	0.0431 (15)	0.0361 (14)	0.0437 (15)	−0.0096 (12)	−0.0107 (12)	−0.0105 (12)
C3	0.0475 (17)	0.0398 (15)	0.0533 (17)	−0.0105 (13)	−0.0115 (13)	−0.0131 (13)
C4	0.0404 (16)	0.0385 (15)	0.073 (2)	−0.0091 (13)	−0.0074 (15)	−0.0153 (15)
C5	0.0507 (18)	0.0400 (16)	0.0600 (19)	−0.0085 (14)	−0.0028 (15)	−0.0010 (14)
C6	0.0524 (18)	0.0459 (17)	0.0472 (17)	−0.0063 (14)	−0.0094 (14)	−0.0025 (13)
C7	0.0393 (15)	0.0379 (14)	0.0455 (15)	−0.0044 (12)	−0.0102 (12)	−0.0117 (12)
C8	0.0424 (16)	0.0395 (14)	0.0429 (15)	−0.0099 (12)	−0.0103 (12)	−0.0116 (12)
C9	0.0423 (16)	0.0534 (17)	0.0510 (16)	−0.0155 (13)	−0.0136 (13)	−0.0142 (14)
C10	0.0496 (18)	0.0541 (17)	0.0458 (16)	−0.0208 (15)	−0.0087 (13)	−0.0116 (14)
C11	0.063 (2)	0.059 (2)	0.066 (2)	−0.0120 (17)	−0.0275 (17)	−0.0062 (17)
C12	0.100 (4)	0.057 (2)	0.175 (5)	−0.034 (2)	−0.038 (4)	−0.019 (3)

Geometric parameters (Å, º) top

Br—C4	1.898 (3)	C4—C5	1.400 (5)
S—O2	1.493 (3)	C5—C6	1.374 (5)
S—C1	1.755 (3)	C5—H5	0.9300
S—C11	1.793 (4)	C6—C7	1.376 (4)
O1—C7	1.370 (3)	C6—H6	0.9300
O1—C8	1.375 (3)	C8—C9	1.481 (4)
O3—C10	1.327 (4)	C9—C10	1.501 (4)
O3—C12	1.454 (5)	C9—H9A	0.9700
O4—C10	1.195 (4)	C9—H9B	0.9700
C1—C8	1.350 (4)	C11—H11A	0.9600
C1—C2	1.451 (4)	C11—H11B	0.9600
C2—C3	1.391 (4)	C11—H11C	0.9600
C2—C7	1.395 (4)	C12—H12A	0.9600
C3—C4	1.377 (4)	C12—H12B	0.9600
C3—H3	0.9300	C12—H12C	0.9600

O2—S—C1	106.07 (14)	C6—C7—C2	123.2 (3)
O2—S—C11	106.21 (17)	C1—C8—O1	111.1 (2)
C1—S—C11	98.55 (16)	C1—C8—C9	133.3 (3)
C7—O1—C8	106.4 (2)	O1—C8—C9	115.6 (2)
C10—O3—C12	116.0 (3)	C8—C9—C10	114.0 (2)
C8—C1—C2	107.2 (3)	C8—C9—H9A	108.8
C8—C1—S	124.7 (2)	C10—C9—H9A	108.8
C2—C1—S	127.9 (2)	C8—C9—H9B	108.8
C3—C2—C7	120.0 (3)	C10—C9—H9B	108.8
C3—C2—C1	135.6 (3)	H9A—C9—H9B	107.7
C7—C2—C1	104.4 (2)	O4—C10—O3	123.4 (3)
C4—C3—C2	116.2 (3)	O4—C10—C9	126.2 (3)
C4—C3—H3	121.9	O3—C10—C9	110.4 (3)
C2—C3—H3	121.9	S—C11—H11A	109.5
C3—C4—C5	123.5 (3)	S—C11—H11B	109.5
C3—C4—Br	118.6 (3)	H11A—C11—H11B	109.5
C5—C4—Br	117.9 (2)	S—C11—H11C	109.5
C6—C5—C4	119.9 (3)	H11A—C11—H11C	109.5
C6—C5—H5	120.0	H11B—C11—H11C	109.5
C4—C5—H5	120.0	O3—C12—H12A	109.5
C5—C6—C7	117.1 (3)	O3—C12—H12B	109.5
C5—C6—H6	121.5	H12A—C12—H12B	109.5
C7—C6—H6	121.5	O3—C12—H12C	109.5
O1—C7—C6	125.9 (3)	H12A—C12—H12C	109.5
O1—C7—C2	110.9 (2)	H12B—C12—H12C	109.5

O2—S—C1—C8	131.5 (3)	C5—C6—C7—C2	−1.3 (5)
C11—S—C1—C8	−118.8 (3)	C3—C2—C7—O1	−177.8 (2)
O2—S—C1—C2	−42.4 (3)	C1—C2—C7—O1	1.1 (3)
C11—S—C1—C2	67.3 (3)	C3—C2—C7—C6	1.4 (4)
C8—C1—C2—C3	177.9 (3)	C1—C2—C7—C6	−179.7 (3)
S—C1—C2—C3	−7.3 (5)	C2—C1—C8—O1	0.1 (3)
C8—C1—C2—C7	−0.7 (3)	S—C1—C8—O1	−174.9 (2)
S—C1—C2—C7	174.1 (2)	C2—C1—C8—C9	−179.8 (3)
C7—C2—C3—C4	−0.3 (4)	S—C1—C8—C9	5.1 (5)
C1—C2—C3—C4	−178.8 (3)	C7—O1—C8—C1	0.6 (3)
C2—C3—C4—C5	−0.8 (4)	C7—O1—C8—C9	−179.5 (2)
C2—C3—C4—Br	178.5 (2)	C1—C8—C9—C10	63.6 (4)
C3—C4—C5—C6	0.9 (5)	O1—C8—C9—C10	−116.3 (3)
Br—C4—C5—C6	−178.4 (2)	C12—O3—C10—O4	0.8 (5)
C4—C5—C6—C7	0.1 (5)	C12—O3—C10—C9	−179.9 (4)
C8—O1—C7—C6	179.7 (3)	C8—C9—C10—O4	−12.9 (5)
C8—O1—C7—C2	−1.1 (3)	C8—C9—C10—O3	167.7 (3)
C5—C6—C7—O1	177.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.43	3.334 (4)	163
C9—H9B···O1ⁱⁱ	0.97	2.59	3.555 (3)	171
C9—H9A···O2ⁱⁱⁱ	0.97	2.22	3.177 (4)	169
C12—H12B···Cg^iv	0.96	2.99	3.903 (4)	159

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₁BrO₄S
M_r	331.18
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	7.9696 (5), 9.1146 (6), 10.3100 (7)
α, β, γ (°)	72.587 (1), 78.716 (1), 69.082 (1)
V (Å³)	664.17 (8)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.25
Crystal size (mm)	0.40 × 0.30 × 0.20

Data collection
Diffractometer	Bruker SMART CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1999)
T_min, T_max	0.327, 0.530
No. of measured, independent and observed [I > 2σ(I)] reflections	3786, 2560, 2084
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.099, 0.98
No. of reflections	2560
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.80

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O2ⁱ	0.93	2.43	3.334 (4)	163
C9—H9B···O1ⁱⁱ	0.97	2.59	3.555 (3)	171
C9—H9A···O2ⁱⁱⁱ	0.97	2.22	3.177 (4)	169
C12—H12B···Cg^iv	0.96	2.99	3.903 (4)	159

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

References

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Volume 64| Part 12| December 2008| Page o2397

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