2-(3-Ethyl-sulfanyl-5-fluoro-1-benzofuran-2-yl)acetic acid.

The title compound, C(12)H(11)FO(3)S, was prepared by alkaline hydrolysis of ethyl 2-(3-ethyl-sulfan-yl-5-fluoro-1-benzofuran-2--yl) acetate. In the crystal structure, the carboxyl groups are involved in inter-molecular O-H⋯O hydrogen bonds, which link the mol-ecules into centrosymmetric dimers. These dimers are further packed into stacks along the b axis by aromatic π-π inter-actions between the furan ring and the benzene ring of neighbouring benzofuran ring systems [centroid-centroid distance = 3.684 (5) Å].

Related literature

For the crystal structures of similar 2–(5–halo–1–benzofuran–2–­yl) acetic acid derivatives, see: Choi et al. (2009a ▶,b ▶). For the pharmacological properties of benzofuran compounds, see: Howlett et al. (1999 ▶); Twyman & Allsop (1999 ▶).

Experimental

Crystal data

C12H11FO3S

M = 254.27

Monoclinic,

a = 10.6009 (9) Å

b = 8.3319 (7) Å

c = 13.395 (1) Å

β = 96.138 (1)°

V = 1176.34 (17) Å3

Z = 4

Mo Kα radiation

μ = 0.28 mm−1

T = 173 K

0.25 × 0.20 × 0.16 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ▶) T min = 0.931, T max = 0.958

9646 measured reflections

2543 independent reflections

1541 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.113

S = 1.16

2543 reflections

159 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.33 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 I. DOI: 10.1107/S160053680903671X/zq2007sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680903671X/zq2007Isup2.hkl

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

C12H11FO3S	F(000) = 528
Mr = 254.27	Dx = 1.436 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2478 reflections
a = 10.6009 (9) Å	θ = 2.3–27.4°
b = 8.3319 (7) Å	µ = 0.28 mm−1
c = 13.395 (1) Å	T = 173 K
β = 96.138 (1)°	Block, colorless
V = 1176.34 (17) Å3	0.25 × 0.20 × 0.16 mm
Z = 4

Bruker SMART CCD diffractometer	2543 independent reflections
Radiation source: fine-focus sealed tube	1541 reflections with I > 2σ(I)
graphite	Rint = 0.072
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.3°
φ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	k = −10→10
Tmin = 0.931, Tmax = 0.958	l = −17→17
9646 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)] = 0.047	Hydrogen site location: difference Fourier map
wR(F2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.P)2 + 1.581P] where P = (Fo2 + 2Fc2)/3
2543 reflections	(Δ/σ)max < 0.001
159 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.33 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	0.76702 (8)	0.59687 (10)	0.63171 (7)	0.0380 (2)
F	0.2776 (2)	0.4175 (3)	0.75176 (16)	0.0561 (6)
O1	0.5990 (2)	0.2294 (2)	0.48565 (15)	0.0279 (5)
O2	0.9881 (2)	0.1796 (3)	0.4247 (2)	0.0459 (7)
H2	1.034 (5)	0.097 (6)	0.437 (4)	0.11 (2)*
O3	0.8642 (2)	0.0735 (3)	0.53184 (18)	0.0403 (6)
C1	0.6717 (3)	0.4365 (3)	0.5848 (2)	0.0252 (7)
C2	0.5483 (3)	0.3918 (3)	0.6122 (2)	0.0247 (7)
C3	0.4702 (3)	0.4454 (4)	0.6824 (2)	0.0327 (8)
H3	0.4934	0.5304	0.7255	0.039*
C4	0.3580 (3)	0.3667 (4)	0.6845 (3)	0.0374 (9)
C5	0.3184 (3)	0.2392 (4)	0.6226 (3)	0.0387 (9)
H5	0.2404	0.1907	0.6280	0.046*
C6	0.3949 (3)	0.1847 (4)	0.5531 (2)	0.0334 (8)
H6	0.3711	0.0992	0.5107	0.040*
C7	0.5087 (3)	0.2634 (3)	0.5496 (2)	0.0251 (7)
C8	0.6966 (3)	0.3365 (4)	0.5101 (2)	0.0263 (7)
C9	0.8058 (3)	0.3237 (4)	0.4507 (2)	0.0344 (8)
H9A	0.8578	0.4190	0.4625	0.041*
H9B	0.7742	0.3219	0.3801	0.041*
C10	0.8882 (3)	0.1785 (4)	0.4735 (2)	0.0290 (7)
C11	0.8469 (4)	0.5118 (4)	0.7462 (3)	0.0505 (11)
H11A	0.8860	0.5981	0.7871	0.061*
H11B	0.7840	0.4618	0.7836	0.061*
C12	0.9460 (4)	0.3907 (5)	0.7297 (3)	0.0584 (12)
H12A	0.9069	0.2989	0.6959	0.088*
H12B	0.9889	0.3583	0.7932	0.088*
H12C	1.0061	0.4369	0.6892	0.088*

	U11	U22	U33	U12	U13	U23
S	0.0381 (5)	0.0222 (4)	0.0500 (5)	−0.0057 (4)	−0.0124 (4)	0.0003 (4)
F	0.0489 (13)	0.0634 (15)	0.0605 (14)	0.0130 (12)	0.0265 (11)	0.0092 (12)
O1	0.0296 (12)	0.0246 (11)	0.0286 (12)	0.0014 (10)	−0.0018 (10)	−0.0065 (9)
O2	0.0306 (14)	0.0502 (17)	0.0602 (17)	0.0095 (13)	0.0200 (13)	0.0200 (14)
O3	0.0360 (14)	0.0379 (14)	0.0499 (15)	0.0090 (11)	0.0177 (12)	0.0116 (12)
C1	0.0288 (17)	0.0182 (15)	0.0268 (16)	0.0005 (13)	−0.0051 (13)	0.0020 (12)
C2	0.0282 (16)	0.0197 (15)	0.0245 (16)	0.0045 (13)	−0.0046 (13)	0.0024 (13)
C3	0.041 (2)	0.0254 (17)	0.0309 (18)	0.0074 (15)	0.0003 (16)	0.0013 (14)
C4	0.036 (2)	0.039 (2)	0.040 (2)	0.0126 (16)	0.0109 (17)	0.0143 (16)
C5	0.0277 (18)	0.0320 (19)	0.056 (2)	−0.0019 (15)	0.0017 (17)	0.0157 (17)
C6	0.0317 (19)	0.0238 (16)	0.042 (2)	0.0001 (15)	−0.0079 (16)	0.0053 (15)
C7	0.0270 (17)	0.0192 (15)	0.0278 (17)	0.0021 (13)	−0.0029 (14)	0.0036 (13)
C8	0.0256 (17)	0.0233 (15)	0.0294 (17)	0.0018 (14)	−0.0003 (14)	0.0020 (13)
C9	0.0333 (19)	0.0324 (18)	0.0375 (19)	0.0064 (15)	0.0047 (16)	0.0048 (15)
C10	0.0265 (18)	0.0307 (17)	0.0298 (18)	−0.0012 (15)	0.0032 (14)	−0.0001 (14)
C11	0.062 (3)	0.042 (2)	0.042 (2)	−0.002 (2)	−0.0234 (19)	−0.0088 (18)
C12	0.051 (2)	0.059 (3)	0.060 (3)	0.002 (2)	−0.017 (2)	0.020 (2)

S—C1	1.751 (3)	C5—C6	1.376 (5)
S—C11	1.815 (4)	C5—H5	0.9300
F—C4	1.371 (4)	C6—C7	1.379 (4)
O1—C8	1.379 (4)	C6—H6	0.9300
O1—C7	1.380 (4)	C8—C9	1.477 (4)
O2—C10	1.303 (4)	C9—C10	1.504 (4)
O2—H2	0.85 (5)	C9—H9A	0.9700
O3—C10	1.217 (4)	C9—H9B	0.9700
C1—C8	1.349 (4)	C11—C12	1.491 (5)
C1—C2	1.445 (4)	C11—H11A	0.9700
C2—C3	1.391 (4)	C11—H11B	0.9700
C2—C7	1.395 (4)	C12—H12A	0.9600
C3—C4	1.362 (5)	C12—H12B	0.9600
C3—H3	0.9300	C12—H12C	0.9600
C4—C5	1.385 (5)
C1—S—C11	101.79 (15)	C1—C8—O1	112.0 (3)
C8—O1—C7	105.8 (2)	C1—C8—C9	132.1 (3)
C10—O2—H2	112 (4)	O1—C8—C9	115.9 (3)
C8—C1—C2	106.5 (3)	C8—C9—C10	114.9 (3)
C8—C1—S	125.9 (3)	C8—C9—H9A	108.6
C2—C1—S	127.5 (2)	C10—C9—H9A	108.6
C3—C2—C7	119.4 (3)	C8—C9—H9B	108.6
C3—C2—C1	135.2 (3)	C10—C9—H9B	108.6
C7—C2—C1	105.5 (3)	H9A—C9—H9B	107.5
C4—C3—C2	116.3 (3)	O3—C10—O2	124.3 (3)
C4—C3—H3	121.8	O3—C10—C9	123.5 (3)
C2—C3—H3	121.8	O2—C10—C9	112.2 (3)
C3—C4—F	118.1 (3)	C12—C11—S	114.3 (3)
C3—C4—C5	124.5 (3)	C12—C11—H11A	108.7
F—C4—C5	117.4 (3)	S—C11—H11A	108.7
C6—C5—C4	119.7 (3)	C12—C11—H11B	108.7
C6—C5—H5	120.2	S—C11—H11B	108.7
C4—C5—H5	120.2	H11A—C11—H11B	107.6
C5—C6—C7	116.6 (3)	C11—C12—H12A	109.5
C5—C6—H6	121.7	C11—C12—H12B	109.5
C7—C6—H6	121.7	H12A—C12—H12B	109.5
C6—C7—O1	126.2 (3)	C11—C12—H12C	109.5
C6—C7—C2	123.5 (3)	H12A—C12—H12C	109.5
O1—C7—C2	110.3 (3)	H12B—C12—H12C	109.5
C11—S—C1—C8	−101.3 (3)	C8—O1—C7—C2	1.0 (3)
C11—S—C1—C2	83.6 (3)	C3—C2—C7—C6	−0.1 (4)
C8—C1—C2—C3	179.5 (3)	C1—C2—C7—C6	179.3 (3)
S—C1—C2—C3	−4.6 (5)	C3—C2—C7—O1	179.8 (3)
C8—C1—C2—C7	0.4 (3)	C1—C2—C7—O1	−0.8 (3)
S—C1—C2—C7	176.2 (2)	C2—C1—C8—O1	0.2 (3)
C7—C2—C3—C4	−0.2 (4)	S—C1—C8—O1	−175.7 (2)
C1—C2—C3—C4	−179.3 (3)	C2—C1—C8—C9	179.1 (3)
C2—C3—C4—F	−179.1 (3)	S—C1—C8—C9	3.2 (5)
C2—C3—C4—C5	0.2 (5)	C7—O1—C8—C1	−0.7 (3)
C3—C4—C5—C6	0.0 (5)	C7—O1—C8—C9	−179.8 (2)
F—C4—C5—C6	179.3 (3)	C1—C8—C9—C10	109.0 (4)
C4—C5—C6—C7	−0.2 (5)	O1—C8—C9—C10	−72.1 (4)
C5—C6—C7—O1	−179.6 (3)	C8—C9—C10—O3	4.1 (5)
C5—C6—C7—C2	0.3 (4)	C8—C9—C10—O2	−175.1 (3)
C8—O1—C7—C6	−179.1 (3)	C1—S—C11—C12	72.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O3i	0.85 (5)	1.81 (5)	2.654 (3)	177 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2⋯O3i	0.85 (5)	1.81 (5)	2.654 (3)	177 (5)

Symmetry code: (i) .