2-(5-Methyl-3-methyl-sulfinyl-1-benzofuran-2-yl)acetic acid.

In the title compound, C(12)H(12)O(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent are located on opposite sides of the plane of the benzofuran fragment. In the crystal structure, inter-molecular C-H⋯O and O-H⋯O hydrogen-bonding inter-actions are found. The structure also exhibits aromatic π-π inter-actions between the furan and benzene rings [centroid-centroid distance = 3.841 (5) Å].

Related literature

For the crystal structures of similar alkyl 2-(5-methyl-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate derivatives, see: Choi et al. (2008 ▶). For the pharmacological properties of benzofuran compounds, see: Howlett et al. (1999 ▶); Twyman & Allsop (1999 ▶). For natural products that contain benzofuran ring systems, see: Akgul & Anil (2003 ▶); von Reuss & König (2004 ▶).

Experimental

Crystal data

C12H12O4S

M = 252.28

Orthorhombic,

a = 7.767 (1) Å

b = 16.248 (2) Å

c = 18.733 (2) Å

V = 2364.1 (5) Å3

Z = 8

Mo Kα radiation

μ = 0.27 mm−1

T = 293 K

0.40 × 0.20 × 0.05 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.899, T max = 0.987

13669 measured reflections

2690 independent reflections

1461 reflections with I > 2σ(I)

R int = 0.110

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.156

S = 1.04

2690 reflections

160 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.45 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809033765/nc2155sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809033765/nc2155Isup2.hkl

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

C12H12O4S	Dx = 1.418 Mg m−3
Mr = 252.28	Melting point = 461–462 K
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2314 reflections
a = 7.767 (1) Å	θ = 2.7–23.2°
b = 16.248 (2) Å	µ = 0.27 mm−1
c = 18.733 (2) Å	T = 293 K
V = 2364.1 (5) Å3	Block, colorless
Z = 8	0.40 × 0.20 × 0.05 mm
F(000) = 1056

Bruker SMART CCD diffractometer	2690 independent reflections
Radiation source: fine-focus sealed tube	1461 reflections with I > 2σ(I)
graphite	Rint = 0.110
Detector resolution: 10.0 pixels mm-1	θmax = 27.5°, θmin = 2.2°
φ and ω scans	h = −8→10
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −20→21
Tmin = 0.899, Tmax = 0.987	l = −24→24
13669 measured reflections

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)] = 0.052	Hydrogen site location: difference Fourier map
wR(F2) = 0.156	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0469P)2 + 5.6706P] where P = (Fo2 + 2Fc2)/3
2690 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

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 > 2sigma(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.

	x	y	z	Uiso*/Ueq
S	0.11771 (12)	0.71553 (6)	0.38153 (5)	0.0201 (2)
O1	0.2472 (3)	0.49764 (16)	0.45410 (13)	0.0239 (6)
O2	0.6841 (4)	0.67768 (18)	0.46398 (15)	0.0285 (7)
H2	0.761 (7)	0.697 (3)	0.437 (3)	0.057 (17)*
O3	0.5236 (4)	0.6591 (2)	0.36700 (15)	0.0429 (9)
O4	−0.0703 (3)	0.73974 (16)	0.38751 (15)	0.0304 (7)
C1	0.1334 (5)	0.6112 (2)	0.40470 (19)	0.0198 (8)
C2	0.0240 (5)	0.5428 (2)	0.38493 (19)	0.0206 (8)
C3	−0.1287 (5)	0.5323 (2)	0.34684 (19)	0.0232 (8)
H3	−0.1837	0.5773	0.3263	0.028*
C4	−0.1973 (5)	0.4540 (2)	0.3400 (2)	0.0262 (9)
C5	−0.1128 (5)	0.3867 (2)	0.3718 (2)	0.0263 (9)
H5	−0.1594	0.3344	0.3664	0.032*
C6	0.0363 (5)	0.3956 (2)	0.4107 (2)	0.0238 (9)
H6	0.0910	0.3509	0.4317	0.029*
C7	0.1005 (5)	0.4747 (2)	0.41678 (19)	0.0201 (8)
C8	0.2619 (5)	0.5814 (2)	0.44641 (18)	0.0203 (8)
C9	0.4120 (5)	0.6207 (2)	0.48186 (19)	0.0228 (9)
H9A	0.4666	0.5806	0.5129	0.027*
H9B	0.3713	0.6656	0.5115	0.027*
C10	0.5441 (5)	0.6535 (2)	0.4304 (2)	0.0218 (8)
C11	−0.3638 (6)	0.4401 (3)	0.2989 (2)	0.0419 (12)
H11A	−0.4395	0.4860	0.3062	0.063*
H11B	−0.4183	0.3907	0.3157	0.063*
H11C	−0.3386	0.4348	0.2490	0.063*
C12	0.1561 (6)	0.7075 (3)	0.2878 (2)	0.0349 (11)
H12A	0.0770	0.6687	0.2674	0.052*
H12B	0.2719	0.6891	0.2798	0.052*
H12C	0.1400	0.7603	0.2659	0.052*

	U11	U22	U33	U12	U13	U23
S	0.0185 (5)	0.0201 (4)	0.0216 (4)	−0.0006 (4)	0.0017 (4)	0.0006 (4)
O1	0.0196 (14)	0.0243 (14)	0.0278 (15)	−0.0018 (11)	−0.0061 (12)	0.0021 (12)
O2	0.0196 (15)	0.0405 (18)	0.0254 (15)	−0.0086 (13)	−0.0019 (13)	0.0023 (13)
O3	0.0280 (18)	0.081 (2)	0.0198 (15)	−0.0110 (17)	−0.0037 (13)	0.0048 (15)
O4	0.0202 (15)	0.0282 (15)	0.0429 (17)	0.0063 (12)	0.0086 (13)	0.0054 (13)
C1	0.020 (2)	0.0197 (19)	0.0195 (18)	−0.0005 (16)	0.0013 (16)	−0.0011 (15)
C2	0.022 (2)	0.024 (2)	0.0159 (18)	0.0014 (16)	0.0032 (16)	−0.0024 (16)
C3	0.023 (2)	0.025 (2)	0.0217 (19)	0.0007 (18)	−0.0037 (17)	0.0020 (16)
C4	0.024 (2)	0.035 (2)	0.0197 (19)	−0.0046 (19)	−0.0036 (17)	−0.0004 (18)
C5	0.033 (2)	0.0207 (19)	0.025 (2)	−0.0072 (19)	0.0007 (19)	−0.0001 (16)
C6	0.024 (2)	0.021 (2)	0.026 (2)	0.0005 (17)	−0.0034 (18)	0.0047 (16)
C7	0.018 (2)	0.025 (2)	0.0181 (18)	0.0005 (17)	−0.0005 (16)	−0.0006 (15)
C8	0.020 (2)	0.025 (2)	0.0169 (18)	−0.0017 (16)	0.0018 (16)	−0.0024 (16)
C9	0.021 (2)	0.028 (2)	0.0186 (18)	−0.0006 (17)	−0.0023 (16)	−0.0018 (16)
C10	0.0144 (19)	0.029 (2)	0.0215 (19)	0.0023 (17)	−0.0009 (16)	−0.0048 (16)
C11	0.037 (3)	0.045 (3)	0.044 (3)	−0.013 (2)	−0.019 (2)	0.010 (2)
C12	0.034 (3)	0.046 (3)	0.025 (2)	0.006 (2)	0.0006 (18)	0.005 (2)

S—O4	1.516 (3)	C4—C11	1.522 (6)
S—C1	1.754 (4)	C5—C6	1.375 (6)
S—C12	1.786 (4)	C5—H5	0.9300
O1—C8	1.374 (4)	C6—C7	1.383 (5)
O1—C7	1.388 (4)	C6—H6	0.9300
O2—C10	1.316 (5)	C8—C9	1.486 (5)
O2—H2	0.85 (5)	C9—C10	1.506 (5)
O3—C10	1.202 (4)	C9—H9A	0.9700
C1—C8	1.356 (5)	C9—H9B	0.9700
C1—C2	1.447 (5)	C11—H11A	0.9600
C2—C7	1.390 (5)	C11—H11B	0.9600
C2—C3	1.394 (5)	C11—H11C	0.9600
C3—C4	1.385 (5)	C12—H12A	0.9600
C3—H3	0.9300	C12—H12B	0.9600
C4—C5	1.408 (5)	C12—H12C	0.9600
O4—S—C1	107.41 (17)	O1—C7—C2	110.7 (3)
O4—S—C12	104.62 (19)	C1—C8—O1	110.7 (3)
C1—S—C12	99.26 (19)	C1—C8—C9	133.0 (4)
C8—O1—C7	106.3 (3)	O1—C8—C9	116.3 (3)
C10—O2—H2	114 (3)	C8—C9—C10	113.6 (3)
C8—C1—C2	107.8 (3)	C8—C9—H9A	108.8
C8—C1—S	122.6 (3)	C10—C9—H9A	108.8
C2—C1—S	129.7 (3)	C8—C9—H9B	108.8
C7—C2—C3	119.1 (3)	C10—C9—H9B	108.8
C7—C2—C1	104.5 (3)	H9A—C9—H9B	107.7
C3—C2—C1	136.4 (4)	O3—C10—O2	124.0 (4)
C4—C3—C2	119.1 (4)	O3—C10—C9	124.7 (4)
C4—C3—H3	120.4	O2—C10—C9	111.3 (3)
C2—C3—H3	120.4	C4—C11—H11A	109.5
C3—C4—C5	119.6 (4)	C4—C11—H11B	109.5
C3—C4—C11	120.7 (4)	H11A—C11—H11B	109.5
C5—C4—C11	119.7 (4)	C4—C11—H11C	109.5
C6—C5—C4	122.3 (4)	H11A—C11—H11C	109.5
C6—C5—H5	118.8	H11B—C11—H11C	109.5
C4—C5—H5	118.8	S—C12—H12A	109.5
C5—C6—C7	116.5 (4)	S—C12—H12B	109.5
C5—C6—H6	121.8	H12A—C12—H12B	109.5
C7—C6—H6	121.8	S—C12—H12C	109.5
C6—C7—O1	125.9 (3)	H12A—C12—H12C	109.5
C6—C7—C2	123.3 (4)	H12B—C12—H12C	109.5
O4—S—C1—C8	−138.0 (3)	C8—O1—C7—C6	−179.5 (4)
C12—S—C1—C8	113.4 (3)	C8—O1—C7—C2	0.8 (4)
O4—S—C1—C2	42.9 (4)	C3—C2—C7—C6	2.4 (6)
C12—S—C1—C2	−65.7 (4)	C1—C2—C7—C6	−179.6 (3)
C8—C1—C2—C7	−0.9 (4)	C3—C2—C7—O1	−177.9 (3)
S—C1—C2—C7	178.3 (3)	C1—C2—C7—O1	0.1 (4)
C8—C1—C2—C3	176.6 (4)	C2—C1—C8—O1	1.5 (4)
S—C1—C2—C3	−4.2 (7)	S—C1—C8—O1	−177.8 (2)
C7—C2—C3—C4	−1.9 (5)	C2—C1—C8—C9	179.3 (4)
C1—C2—C3—C4	−179.1 (4)	S—C1—C8—C9	0.0 (6)
C2—C3—C4—C5	0.4 (6)	C7—O1—C8—C1	−1.4 (4)
C2—C3—C4—C11	179.9 (4)	C7—O1—C8—C9	−179.6 (3)
C3—C4—C5—C6	0.8 (6)	C1—C8—C9—C10	−66.5 (5)
C11—C4—C5—C6	−178.8 (4)	O1—C8—C9—C10	111.2 (4)
C4—C5—C6—C7	−0.3 (6)	C8—C9—C10—O3	10.1 (6)
C5—C6—C7—O1	179.1 (3)	C8—C9—C10—O2	−171.7 (3)
C5—C6—C7—C2	−1.2 (6)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9B···O4i	0.97	2.48	3.339 (5)	148
O2—H2···O4ii	0.85 (6)	1.74 (6)	2.590 (4)	175 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9B⋯O4i	0.97	2.48	3.339 (5)	148
O2—H2⋯O4ii	0.85 (6)	1.74 (6)	2.590 (4)	175 (5)

Symmetry codes: (i) ; (ii) .