2-(5-Fluoro-7-methyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetic acid.

The title compound, C(12)H(11)FO(3)S, was prepared by alkaline hydrolysis of ethyl 2-(5-fluoro-7-methyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate. In the crystal, the carboxyl groups are involved in inter-molecular O-H⋯O hydrogen bonds, which link the mol-ecules into centrosymmetric dimers.

Related literature

For the pharmacological activity of benzofuran compounds, see: Aslam et al. (2009 ▶); Galal et al. (2009 ▶); Khan et al. (2005 ▶). For natural products with benzofuran rings, see: Akgul & Anil (2003 ▶); Soekamto et al. (2003 ▶). For structural studies of related 2-(5-halo-3-methyl­sulfanyl-1-benzofuran-2-yl)acetic acid derivatives, see: Choi et al. (2009 ▶).

Experimental

Crystal data

C12H11FO3S

M = 254.27

Monoclinic,

a = 16.1747 (9) Å

b = 4.9242 (3) Å

c = 14.4572 (7) Å

β = 91.701 (3)°

V = 1150.97 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 173 K

0.42 × 0.19 × 0.09 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.889, T max = 0.975

10241 measured reflections

2873 independent reflections

2114 reflections with I > 2σ(I)

R int = 0.050

Refinement

R[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.153

S = 1.05

2873 reflections

156 parameters

H-atom parameters constrained

Δρmax = 0.38 e Å−3

Δρmin = −0.27 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); 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 datablock(s) global, I. DOI: 10.1107/S1600536811026729/xu5266sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026729/xu5266Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811026729/xu5266Isup3.cml

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

C12H11FO3S	F(000) = 528
Mr = 254.27	Dx = 1.467 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3638 reflections
a = 16.1747 (9) Å	θ = 2.5–27.9°
b = 4.9242 (3) Å	µ = 0.29 mm−1
c = 14.4572 (7) Å	T = 173 K
β = 91.701 (3)°	Block, colourless
V = 1150.97 (11) Å3	0.42 × 0.19 × 0.09 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	2873 independent reflections
Radiation source: rotating anode	2114 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.050
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.5°
φ and ω scans	h = −19→21
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −6→6
Tmin = 0.889, Tmax = 0.975	l = −19→19
10241 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)] = 0.048	Hydrogen site location: difference Fourier map
wR(F2) = 0.153	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0891P)2 + 0.0162P] where P = (Fo2 + 2Fc2)/3
2873 reflections	(Δ/σ)max < 0.001
156 parameters	Δρmax = 0.38 e Å−3
0 restraints	Δρmin = −0.27 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
S1	0.15190 (3)	0.70323 (12)	0.30067 (3)	0.0375 (2)
F1	0.38947 (9)	−0.1018 (3)	0.42507 (7)	0.0606 (5)
O1	0.29563 (7)	0.4092 (3)	0.10941 (7)	0.0292 (3)
O2	0.10398 (10)	0.3674 (3)	0.03782 (12)	0.0558 (5)
H2	0.0565	0.3189	0.0195	0.084*
O3	0.05132 (8)	0.7769 (3)	0.01681 (10)	0.0438 (4)
C1	0.22446 (10)	0.5379 (4)	0.23383 (11)	0.0273 (4)
C2	0.28406 (10)	0.3388 (4)	0.26357 (10)	0.0255 (4)
C3	0.30513 (12)	0.2144 (4)	0.34788 (11)	0.0324 (5)
H3	0.2782	0.2579	0.4035	0.039*
C4	0.36662 (11)	0.0275 (5)	0.34518 (11)	0.0355 (5)
C5	0.40838 (11)	−0.0469 (4)	0.26625 (11)	0.0337 (5)
H5	0.4506	−0.1811	0.2700	0.040*
C6	0.38838 (10)	0.0749 (4)	0.18228 (11)	0.0291 (4)
C7	0.32623 (11)	0.2652 (4)	0.18496 (10)	0.0257 (4)
C8	0.23433 (10)	0.5719 (4)	0.14195 (11)	0.0286 (4)
C9	0.43079 (12)	0.0035 (5)	0.09414 (12)	0.0402 (5)
H9A	0.3896	−0.0592	0.0479	0.060*
H9B	0.4713	−0.1410	0.1065	0.060*
H9C	0.4591	0.1642	0.0707	0.060*
C10	0.18996 (12)	0.7432 (5)	0.07219 (13)	0.0358 (5)
H10A	0.2252	0.7646	0.0179	0.043*
H10B	0.1815	0.9259	0.0989	0.043*
C11	0.10771 (11)	0.6315 (4)	0.04024 (11)	0.0292 (4)
C12	0.07261 (13)	0.4483 (5)	0.30180 (15)	0.0471 (6)
H12A	0.0508	0.4187	0.2386	0.071*
H12B	0.0278	0.5087	0.3411	0.071*
H12C	0.0959	0.2782	0.3263	0.071*

	U11	U22	U33	U12	U13	U23
S1	0.0334 (3)	0.0289 (4)	0.0506 (3)	0.0038 (2)	0.0054 (2)	−0.0077 (2)
F1	0.0761 (9)	0.0696 (12)	0.0360 (6)	0.0303 (8)	−0.0012 (5)	0.0216 (6)
O1	0.0293 (6)	0.0322 (8)	0.0258 (5)	0.0010 (6)	−0.0025 (4)	0.0047 (5)
O2	0.0470 (9)	0.0267 (9)	0.0917 (11)	−0.0022 (8)	−0.0345 (8)	0.0036 (9)
O3	0.0319 (8)	0.0305 (9)	0.0680 (9)	0.0070 (7)	−0.0143 (7)	0.0012 (7)
C1	0.0244 (8)	0.0239 (10)	0.0335 (8)	−0.0010 (8)	−0.0007 (6)	−0.0001 (8)
C2	0.0238 (8)	0.0249 (10)	0.0279 (7)	−0.0015 (8)	0.0001 (6)	−0.0010 (7)
C3	0.0373 (10)	0.0343 (12)	0.0258 (7)	0.0002 (9)	0.0020 (7)	0.0027 (8)
C4	0.0401 (10)	0.0375 (13)	0.0286 (8)	0.0040 (10)	−0.0042 (7)	0.0097 (8)
C5	0.0296 (9)	0.0306 (12)	0.0406 (9)	0.0063 (9)	−0.0022 (7)	0.0001 (9)
C6	0.0246 (8)	0.0307 (12)	0.0321 (8)	−0.0019 (8)	0.0007 (6)	−0.0042 (8)
C7	0.0247 (8)	0.0278 (11)	0.0243 (7)	−0.0033 (8)	−0.0032 (6)	0.0021 (7)
C8	0.0240 (8)	0.0251 (11)	0.0362 (8)	−0.0015 (8)	−0.0052 (6)	0.0024 (8)
C9	0.0342 (10)	0.0504 (15)	0.0362 (9)	0.0065 (10)	0.0058 (7)	−0.0090 (9)
C10	0.0359 (10)	0.0290 (11)	0.0420 (9)	−0.0021 (9)	−0.0099 (8)	0.0080 (9)
C11	0.0324 (9)	0.0257 (11)	0.0291 (7)	−0.0007 (9)	−0.0042 (6)	0.0034 (8)
C12	0.0375 (11)	0.0407 (15)	0.0637 (12)	−0.0032 (11)	0.0121 (9)	−0.0064 (11)

S1—C1	1.7440 (17)	C5—C6	1.384 (2)
S1—C12	1.795 (2)	C5—H5	0.9500
F1—C4	1.3605 (19)	C6—C7	1.376 (3)
O1—C8	1.369 (2)	C6—C9	1.507 (2)
O1—C7	1.382 (2)	C8—C10	1.484 (3)
O2—C11	1.303 (2)	C9—H9A	0.9800
O2—H2	0.8400	C9—H9B	0.9800
O3—C11	1.200 (2)	C9—H9C	0.9800
C1—C8	1.353 (2)	C10—C11	1.500 (3)
C1—C2	1.432 (3)	C10—H10A	0.9900
C2—C7	1.391 (2)	C10—H10B	0.9900
C2—C3	1.397 (2)	C12—H12A	0.9800
C3—C4	1.356 (3)	C12—H12B	0.9800
C3—H3	0.9500	C12—H12C	0.9800
C4—C5	1.392 (2)
C1—S1—C12	99.86 (10)	C1—C8—O1	111.87 (15)
C8—O1—C7	105.96 (12)	C1—C8—C10	131.99 (18)
C11—O2—H2	109.5	O1—C8—C10	116.10 (15)
C8—C1—C2	106.36 (15)	C6—C9—H9A	109.5
C8—C1—S1	125.95 (15)	C6—C9—H9B	109.5
C2—C1—S1	127.69 (12)	H9A—C9—H9B	109.5
C7—C2—C3	119.05 (17)	C6—C9—H9C	109.5
C7—C2—C1	105.98 (14)	H9A—C9—H9C	109.5
C3—C2—C1	134.97 (16)	H9B—C9—H9C	109.5
C4—C3—C2	115.62 (15)	C8—C10—C11	114.05 (16)
C4—C3—H3	122.2	C8—C10—H10A	108.7
C2—C3—H3	122.2	C11—C10—H10A	108.7
C3—C4—F1	118.29 (15)	C8—C10—H10B	108.7
C3—C4—C5	125.18 (16)	C11—C10—H10B	108.7
F1—C4—C5	116.52 (18)	H10A—C10—H10B	107.6
C6—C5—C4	119.90 (18)	O3—C11—O2	123.63 (18)
C6—C5—H5	120.0	O3—C11—C10	121.85 (19)
C4—C5—H5	120.0	O2—C11—C10	114.49 (17)
C7—C6—C5	115.00 (15)	S1—C12—H12A	109.5
C7—C6—C9	122.29 (16)	S1—C12—H12B	109.5
C5—C6—C9	122.71 (17)	H12A—C12—H12B	109.5
C6—C7—O1	124.91 (14)	S1—C12—H12C	109.5
C6—C7—C2	125.25 (16)	H12A—C12—H12C	109.5
O1—C7—C2	109.83 (16)	H12B—C12—H12C	109.5
C12—S1—C1—C8	97.22 (19)	C9—C6—C7—C2	179.39 (18)
C12—S1—C1—C2	−81.79 (19)	C8—O1—C7—C6	179.17 (18)
C8—C1—C2—C7	−0.3 (2)	C8—O1—C7—C2	−0.02 (19)
S1—C1—C2—C7	178.89 (14)	C3—C2—C7—C6	0.3 (3)
C8—C1—C2—C3	−179.4 (2)	C1—C2—C7—C6	−179.00 (18)
S1—C1—C2—C3	−0.2 (3)	C3—C2—C7—O1	179.47 (16)
C7—C2—C3—C4	0.0 (3)	C1—C2—C7—O1	0.2 (2)
C1—C2—C3—C4	179.0 (2)	C2—C1—C8—O1	0.3 (2)
C2—C3—C4—F1	−179.57 (17)	S1—C1—C8—O1	−178.91 (13)
C2—C3—C4—C5	−0.3 (3)	C2—C1—C8—C10	178.18 (19)
C3—C4—C5—C6	0.5 (3)	S1—C1—C8—C10	−1.0 (3)
F1—C4—C5—C6	179.75 (17)	C7—O1—C8—C1	−0.2 (2)
C4—C5—C6—C7	−0.3 (3)	C7—O1—C8—C10	−178.42 (15)
C4—C5—C6—C9	−179.8 (2)	C1—C8—C10—C11	−77.6 (3)
C5—C6—C7—O1	−179.19 (16)	O1—C8—C10—C11	100.2 (2)
C9—C6—C7—O1	0.3 (3)	C8—C10—C11—O3	148.89 (18)
C5—C6—C7—C2	−0.1 (3)	C8—C10—C11—O2	−32.9 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.84	1.87	2.706 (2)	177

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.84	1.87	2.706 (2)	177

Symmetry code: (i) .