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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 8| August 2009| Page o1813
doi:10.1107/S160053680902594X

2-(5-Fluoro-3-methyl­sulfanyl-1-benzo­furan-2-yl)acetic acid

Hong Dae Choi,a Pil Ja Seo,a Byeng Wha Sonb and Uk Leeb*

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 1 July 2009; accepted 4 July 2009; online 11 July 2009)

The title compound, C11H9FO3S, was prepared by alkaline hydrolysis of ethyl 2-(5-fluoro-3-methyl­sulfanyl-1-benzofuran-2-yl)acetate. In the crystal structure, the carboxyl groups are involved in inter­molecular O—H⋯O hydrogen bonds, which link the mol­ecules into centrosymmetric dimers. These dimers are further packed into stacks along the b axis by inter­molecular C—H⋯O and C—H⋯F inter­actions.

Related literature

For the crystal structures of similar 2-(3-methyl­sulfanyl-1-benzofuran-2-yl) acetic acid derivatives, see: Choi et al. (2009a[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009a). Acta Cryst. E65, o563.],b[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o1527.]). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999[Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283-289.]); Twyman & Allsop (1999[Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383-9384.]).

[Scheme 1]

Experimental

Crystal data

  • C11H9FO3S

  • Mr = 240.24

  • Monoclinic, P 21 /c

  • a = 7.5179 (4) Å

  • b = 27.325 (2) Å

  • c = 5.0582 (3) Å

  • β = 90.478 (1)°

  • V = 1039.05 (11) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.31 mm−1

  • T = 173 K

  • 0.40 × 0.40 × 0.20 mm
Data collection

  • Bruker SMART CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1999[Sheldrick, G. M. (1999). SADABS. University of Göttingen, Germany.]) Tmin = 0.885, Tmax = 0.940

  • 5774 measured reflections

  • 2015 independent reflections

  • 1758 reflections with I > 2σ(I)

  • Rint = 0.016
Refinement

  • R[F2 > 2σ(F2)] = 0.028

  • wR(F2) = 0.076

  • S = 1.10

  • 2015 reflections

  • 150 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.26 e Å−3

  • Δρmin = −0.21 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C6—H6⋯O3i 0.93 2.52 3.2896 (19) 141
C6—H6⋯O3ii 0.93 2.51 3.296 (2) 143
O2—H2⋯O3iii 0.84 (2) 1.85 (2) 2.6902 (17) 178 (2)
C11—H11B⋯Fiv 0.96 2.69 3.572 (2) 153
C11—H11B⋯Fv 0.96 2.67 3.361 (2) 130
Symmetry codes: (i) x+1, y, z-1; (ii) -x+1, -y+1, -z+1; (iii) -x, -y+1, -z+1; (iv) [x-1, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]; (v) x-1, y, z+1.

Data collection: SMART (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2001[Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680902594X/rn2061sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680902594X/rn2061Isup2.hkl

checkCIF report


Comment top

The benzofuran ring systems have been attracted considerable interest in the view of their pharmacological properties (Howlett et al., 1999; Twyman & Allsop, 1999). As a part of our ongoing studies on the synthesis and structures of 2-(3-methylsulfanyl-1-benzofuran-2-yl)acetic acid analogues, the crystal structure of 2-(5-bromo-3-methylsulfanyl-1-benzofuran-2-yl)acetic acid (Choi et al., 2009a) and 2-(5-isopropyl-3-methylsulfanyl-1-benzofuran-2-yl)acetic acid (Choi et al., 2009b) have been described in the literature. Here we report the crystal structure of the title compound, 2-(5-fluoro-3-methylsulfanyl-1-benzofuran-2-yl)acetic acid (Fig. 1).

The benzofuran unit is essentially planar, with a mean deviation of 0.005 (1) Å from the least-squares plane defined by the nine constituent atoms. In the crystal structure, the carboxyl groups are involved in intermolecular O–H···O hydrogen bonds (Table 1 and Fig. 2), which link the molecules into centrosymmetric dimers. These dimers are further packed into stacks along the b axis by intermolecular C–H···O and C–H···F interactions; the first between an H atom of benzofuran ring and the C═O unit, with C6–H6···O3i and C6–H6···O3ii, the second between a methyl H atom of methylsulfanyl group and the fluorine atom of the benzofuran ring, with C11–H11B···Fiv and C11–H11B···Fv, respectively (Table 1 and Fig. 2).

Related literature top

For the crystal structures of similar 2-(3-methylsulfanyl-1-benzofuran-2-yl) acetic acid derivatives, see: Choi et al. (2009a,b). For the pharmacological activity of benzofuran compounds, see: Howlett et al. (1999); Twyman & Allsop (1999).

Experimental top

Ethyl 2-(5-fluoro-3-methylsulfanyl-1-benzofuran-2-yl)acetate (402 mg, 1.5 mmol) was added to a solution of potassium hydroxide (505 mg, 9.0 mmol) in water (20 ml) and methanol (20 ml), and the mixture was refluxed for 6h, then cooled. Water was added, and the solution was extracted with dichloromethane. The aqueous layer was acidified to pH 1 with concentrated hydrochloric acid and then extracted with chloroform, dried over magnesium sulfate, filtered and concentrated under vacuum. The residue was purified by column chromatography (ethyl acetate) to afford the title compound as a colorless solid [yield 84%, m.p. 438-439 K; Rf = 0.6 (ethyl acetate)]. Single crystals suitable for X-ray diffraction were prepared by evaporation of a solution of the title compound in benzene at room temperature.

Refinement top

The H atom of O2 was positioned in a difference Fourier map and refined freely. The other H atoms were positioned geometrically and refined using a riding model, with C–H = 0.93 Å for the aryl, 0.97 Å for the methylene, and 0.96 Å for the methyl H atoms with Uiso(H) = 1.2Ueq(C) for the aryl and methylene H atoms, and 1.5Ueq(C) for methyl H atoms.

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
[Figure 1] Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small cycles of arbitrary radius.
[Figure 2] Fig. 2. The O–H···O hydrogen bonds, and C–H···O, and C–H···F interactions (dotted lines) in the title compound. [Symmetry code: (i) 1 + x, y, - 1 + z; (ii) 1 - x, 1 - y, 1 - z; (iii) - x, 1 - y, 1 - z; (iv) x - 1, -y + 1/2, z + 1/2; (v) x - 1, y, z + 1.]
2-(5-Fluoro-3-methylsulfanyl-1-benzofuran-2-yl)acetic acid top
Crystal data top
C11H9FO3SF(000) = 496
Mr = 240.24Dx = 1.536 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3920 reflections
a = 7.5179 (4) Åθ = 2.2–27.5°
b = 27.325 (2) ŵ = 0.31 mm−1
c = 5.0582 (3) ÅT = 173 K
β = 90.478 (1)°Block, colourless
V = 1039.05 (11) Å30.40 × 0.40 × 0.20 mm
Z = 4
Data collection top
Bruker SMART CCD
diffractometer		2015 independent reflections
Radiation source: fine-focus sealed tube1758 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
Detector resolution: 10.0 pixels mm-1θmax = 26.0°, θmin = 2.8°
ϕ and ω scansh = −8→9
Absorption correction: multi-scan
(SADABS; Sheldrick, 1999)		k = −33→31
Tmin = 0.885, Tmax = 0.940l = −5→6
5774 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.028Hydrogen site location: difference Fourier map
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.10 w = 1/[σ2(Fo2) + (0.0321P)2 + 0.495P]
where P = (Fo2 + 2Fc2)/3
2015 reflections(Δ/σ)max < 0.001
150 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.21 e Å−3
Crystal data top
C11H9FO3SV = 1039.05 (11) Å3
Mr = 240.24Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.5179 (4) ŵ = 0.31 mm−1
b = 27.325 (2) ÅT = 173 K
c = 5.0582 (3) Å0.40 × 0.40 × 0.20 mm
β = 90.478 (1)°
Data collection top
Bruker SMART CCD
diffractometer		2015 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1999)		1758 reflections with I > 2σ(I)
Tmin = 0.885, Tmax = 0.940Rint = 0.016
5774 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0280 restraints
wR(F2) = 0.076H atoms treated by a mixture of independent and constrained refinement
S = 1.10Δρmax = 0.26 e Å−3
2015 reflectionsΔρmin = −0.21 e Å−3
150 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S0.31784 (5)0.316516 (15)0.58563 (8)0.02756 (13)
F0.83216 (14)0.28556 (4)−0.2451 (2)0.0378 (3)
O10.59504 (15)0.43332 (4)0.3745 (2)0.0255 (3)
O20.19605 (18)0.46681 (5)0.3551 (2)0.0343 (3)
H20.102 (3)0.4823 (9)0.316 (4)0.047 (6)*
O30.09836 (15)0.48144 (4)0.7637 (2)0.0268 (3)
C10.4579 (2)0.36074 (6)0.4469 (3)0.0217 (3)
C20.58779 (19)0.35365 (6)0.2404 (3)0.0211 (3)
C30.6420 (2)0.31379 (6)0.0878 (3)0.0231 (3)
H30.59210.28290.10670.028*
C40.7740 (2)0.32324 (6)−0.0924 (3)0.0251 (3)
C50.8516 (2)0.36865 (6)−0.1307 (3)0.0277 (4)
H50.93940.3725−0.25750.033*
C60.7982 (2)0.40828 (6)0.0203 (3)0.0264 (3)
H60.84780.4392−0.00060.032*
C70.6668 (2)0.39915 (6)0.2039 (3)0.0224 (3)
C80.4683 (2)0.40835 (6)0.5179 (3)0.0232 (3)
C90.3703 (2)0.43787 (6)0.7168 (3)0.0277 (4)
H9A0.45130.46200.79090.033*
H9B0.33450.41640.85940.033*
C100.2076 (2)0.46410 (5)0.6137 (3)0.0219 (3)
C110.1570 (2)0.30916 (8)0.3207 (3)0.0372 (4)
H11A0.09730.33970.28960.056*
H11B0.07150.28470.36900.056*
H11C0.21690.29910.16270.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S0.0263 (2)0.0334 (2)0.0230 (2)−0.00356 (16)0.00305 (15)0.00559 (16)
F0.0415 (6)0.0317 (5)0.0406 (6)0.0029 (4)0.0146 (5)−0.0114 (4)
O10.0268 (6)0.0213 (5)0.0285 (6)0.0022 (4)0.0046 (5)−0.0023 (4)
O20.0339 (7)0.0485 (8)0.0207 (6)0.0195 (6)0.0010 (5)−0.0011 (5)
O30.0251 (6)0.0318 (6)0.0234 (6)0.0067 (5)0.0057 (4)0.0003 (4)
C10.0189 (7)0.0249 (8)0.0215 (7)0.0035 (6)0.0008 (6)0.0025 (6)
C20.0174 (7)0.0238 (8)0.0219 (7)0.0022 (6)−0.0014 (6)0.0025 (6)
C30.0226 (8)0.0211 (7)0.0257 (8)0.0011 (6)−0.0012 (6)0.0008 (6)
C40.0237 (8)0.0261 (8)0.0254 (8)0.0051 (6)0.0009 (6)−0.0048 (6)
C50.0216 (8)0.0346 (9)0.0269 (8)−0.0005 (7)0.0050 (6)0.0007 (7)
C60.0241 (8)0.0243 (8)0.0308 (8)−0.0033 (6)0.0027 (6)0.0011 (6)
C70.0216 (8)0.0212 (7)0.0244 (7)0.0029 (6)−0.0003 (6)−0.0016 (6)
C80.0202 (8)0.0275 (8)0.0218 (7)0.0045 (6)0.0008 (6)0.0017 (6)
C90.0286 (9)0.0319 (9)0.0224 (8)0.0085 (7)0.0005 (6)−0.0028 (6)
C100.0236 (8)0.0197 (7)0.0225 (7)−0.0001 (6)0.0028 (6)−0.0015 (6)
C110.0322 (10)0.0500 (11)0.0293 (9)−0.0112 (8)0.0006 (7)−0.0013 (8)
Geometric parameters (Å, º) top
S—C11.753 (2)C3—H30.9300
S—C111.809 (2)C4—C51.385 (2)
F—C41.361 (2)C5—C61.386 (2)
O1—C81.382 (2)C5—H50.9300
O1—C71.384 (2)C6—C71.385 (2)
O2—C101.312 (2)C6—H60.9300
O2—H20.84 (2)C8—C91.489 (2)
O3—C101.219 (2)C9—C101.507 (2)
C1—C81.352 (2)C9—H9A0.9700
C1—C21.449 (2)C9—H9B0.9700
C2—C71.391 (2)C11—H11A0.9600
C2—C31.398 (2)C11—H11B0.9600
C3—C41.378 (2)C11—H11C0.9600
C1—S—C11100.36 (8)O1—C7—C6125.50 (14)
C8—O1—C7105.54 (12)O1—C7—C2110.57 (13)
C10—O2—H2107.9 (15)C6—C7—C2123.93 (14)
C8—C1—C2106.38 (13)C1—C8—O1111.99 (13)
C8—C1—S126.22 (12)C1—C8—C9132.27 (15)
C2—C1—S127.38 (12)O1—C8—C9115.73 (14)
C7—C2—C3119.76 (14)C8—C9—C10115.38 (13)
C7—C2—C1105.51 (13)C8—C9—H9A108.4
C3—C2—C1134.72 (14)C10—C9—H9A108.4
C4—C3—C2115.75 (14)C8—C9—H9B108.4
C4—C3—H3122.1C10—C9—H9B108.4
C2—C3—H3122.1H9A—C9—H9B107.5
F—C4—C3118.04 (14)O3—C10—O2123.98 (15)
F—C4—C5117.43 (14)O3—C10—C9121.25 (14)
C3—C4—C5124.53 (14)O2—C10—C9114.76 (13)
C4—C5—C6119.90 (14)S—C11—H11A109.5
C4—C5—H5120.0S—C11—H11B109.5
C6—C5—H5120.0H11A—C11—H11B109.5
C7—C6—C5116.12 (15)S—C11—H11C109.5
C7—C6—H6121.9H11A—C11—H11C109.5
C5—C6—H6121.9H11B—C11—H11C109.5
C11—S—C1—C8107.19 (15)C5—C6—C7—C2−0.6 (2)
C11—S—C1—C2−74.59 (15)C3—C2—C7—O1−179.70 (13)
C8—C1—C2—C7−0.23 (17)C1—C2—C7—O10.38 (17)
S—C1—C2—C7−178.73 (12)C3—C2—C7—C60.6 (2)
C8—C1—C2—C3179.87 (17)C1—C2—C7—C6−179.33 (15)
S—C1—C2—C31.4 (3)C2—C1—C8—O1−0.01 (17)
C7—C2—C3—C40.0 (2)S—C1—C8—O1178.52 (11)
C1—C2—C3—C4179.93 (16)C2—C1—C8—C9179.85 (16)
C2—C3—C4—F179.70 (14)S—C1—C8—C9−1.6 (3)
C2—C3—C4—C5−0.7 (2)C7—O1—C8—C10.24 (17)
F—C4—C5—C6−179.66 (14)C7—O1—C8—C9−179.65 (13)
C3—C4—C5—C60.7 (3)C1—C8—C9—C10−92.8 (2)
C4—C5—C6—C7−0.1 (2)O1—C8—C9—C1087.07 (18)
C8—O1—C7—C6179.32 (15)C8—C9—C10—O3165.74 (15)
C8—O1—C7—C2−0.39 (16)C8—C9—C10—O2−14.8 (2)
C5—C6—C7—O1179.77 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C6—H6···O3i0.932.523.2896 (19)141
C6—H6···O3ii0.932.513.296 (2)143
O2—H2···O3iii0.84 (2)1.85 (2)2.6902 (17)178 (2)
C11—H11B···Fiv0.962.693.572 (2)153
C11—H11B···Fv0.962.673.361 (2)130
Symmetry codes: (i) x+1, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) x−1, −y+1/2, z+1/2; (v) x−1, y, z+1.

Experimental details

Crystal data
Chemical formulaC11H9FO3S
Mr240.24
Crystal system, space groupMonoclinic, P21/c
Temperature (K)173
a, b, c (Å)7.5179 (4), 27.325 (2), 5.0582 (3)
β (°) 90.478 (1)
V (Å3)1039.05 (11)
Z4
Radiation typeMo Kα
µ (mm−1)0.31
Crystal size (mm)0.40 × 0.40 × 0.20
Data collection
DiffractometerBruker SMART CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1999)
Tmin, Tmax0.885, 0.940
No. of measured, independent and
observed [I > 2σ(I)] reflections		5774, 2015, 1758
Rint0.016
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.028, 0.076, 1.10
No. of reflections2015
No. of parameters150
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.26, −0.21

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···AD—HH···AD···AD—H···A
C6—H6···O3i0.932.523.2896 (19)140.6
C6—H6···O3ii0.932.513.296 (2)142.6
O2—H2···O3iii0.84 (2)1.85 (2)2.6902 (17)178 (2)
C11—H11B···Fiv0.962.693.572 (2)152.8
C11—H11B···Fv0.962.673.361 (2)129.7
Symmetry codes: (i) x+1, y, z−1; (ii) −x+1, −y+1, −z+1; (iii) −x, −y+1, −z+1; (iv) x−1, −y+1/2, z+1/2; (v) x−1, y, z+1.
 

References

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 First citationBruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
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 First citationChoi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009b). Acta Cryst. E65, o1527.  Web of Science CSD CrossRef IUCr Journals Google Scholar
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 First citationHowlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283–289.  Web of Science CrossRef PubMed CAS Google Scholar
 First citationSheldrick, G. M. (1999). SADABS. University of Göttingen, Germany.  Google Scholar
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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 65| Part 8| August 2009| Page o1813
doi:10.1107/S160053680902594X
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