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

The title compound, C(14)H(15)FO(3)S, was prepared by alkaline hydrolysis of ethyl 2-(5-fluoro-3-isopropyl-sulfanyl-7-methyl-1-benzofuran-2-yl)acetate. In the crystal, mol-ecules are linked via pairs of O-H⋯O hydrogen bonds, forming inversion dimers. These dimers are connected by weak C-H⋯O hydrogen bonds.

Related literature

For background information and the crystal structures of related compounds, see: Seo et al. (2011 ▶, 2012 ▶).

Experimental

Crystal data

C14H15FO3S

M = 282.32

Triclinic,

a = 8.4365 (2) Å

b = 9.2771 (2) Å

c = 9.7956 (2) Å

α = 91.404 (1)°

β = 91.2710 (1)°

γ = 115.111 (1)°

V = 693.55 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.25 mm−1

T = 173 K

0.35 × 0.32 × 0.28 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.919, T max = 0.934

12921 measured reflections

3467 independent reflections

2946 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.051

wR(F 2) = 0.155

S = 1.06

3467 reflections

179 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.93 e Å−3

Δρmin = −0.44 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/S1600536812008240/ld2050sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812008240/ld2050Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812008240/ld2050Isup3.cml

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

C14H15FO3S	Z = 2
Mr = 282.32	F(000) = 296
Triclinic, P1	Dx = 1.352 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4365 (2) Å	Cell parameters from 5886 reflections
b = 9.2771 (2) Å	θ = 2.4–28.4°
c = 9.7956 (2) Å	µ = 0.25 mm−1
α = 91.404 (1)°	T = 173 K
β = 91.2710 (1)°	Block, colourless
γ = 115.111 (1)°	0.35 × 0.32 × 0.28 mm
V = 693.55 (3) Å3

Bruker SMART APEXII CCD diffractometer	3467 independent reflections
Radiation source: rotating anode	2946 reflections with I > 2σ(I)
Graphite multilayer monochromator	Rint = 0.028
Detector resolution: 10.0 pixels mm-1	θmax = 28.4°, θmin = 2.1°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→12
Tmin = 0.919, Tmax = 0.934	l = −13→13
12921 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)] = 0.051	Hydrogen site location: difference Fourier map
wR(F2) = 0.155	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0853P)2 + 0.3723P] where P = (Fo2 + 2Fc2)/3
3467 reflections	(Δ/σ)max < 0.001
179 parameters	Δρmax = 0.93 e Å−3
0 restraints	Δρmin = −0.44 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	0.64151 (7)	0.31790 (6)	0.28518 (5)	0.03564 (17)
F1	0.78061 (17)	0.98655 (14)	0.35845 (16)	0.0503 (4)
O1	0.23013 (17)	0.40794 (15)	0.34150 (13)	0.0310 (3)
O2	0.1261 (3)	0.16845 (17)	0.07988 (16)	0.0552 (5)
O3	0.0331 (2)	−0.07438 (16)	0.15984 (16)	0.0434 (4)
H3O	−0.022 (5)	−0.102 (5)	0.082 (4)	0.097 (13)*
C1	0.4901 (2)	0.3980 (2)	0.30894 (17)	0.0273 (4)
C2	0.5220 (2)	0.5633 (2)	0.32776 (16)	0.0261 (3)
C3	0.6709 (2)	0.7080 (2)	0.33113 (19)	0.0309 (4)
H3	0.7852	0.7141	0.3203	0.037*
C4	0.6403 (3)	0.8411 (2)	0.3512 (2)	0.0343 (4)
C5	0.4765 (3)	0.8394 (2)	0.3669 (2)	0.0348 (4)
H5	0.4664	0.9371	0.3791	0.042*
C6	0.3272 (3)	0.6965 (2)	0.36477 (18)	0.0312 (4)
C7	0.3583 (2)	0.5618 (2)	0.34579 (17)	0.0273 (4)
C8	0.3153 (2)	0.3132 (2)	0.31893 (17)	0.0287 (4)
C9	0.1464 (3)	0.6865 (3)	0.3815 (2)	0.0426 (5)
H9A	0.0604	0.5752	0.3705	0.064*
H9B	0.1222	0.7497	0.3122	0.064*
H9C	0.1386	0.7283	0.4728	0.064*
C10	0.2049 (3)	0.1387 (2)	0.30994 (19)	0.0349 (4)
H10A	0.1139	0.1115	0.3792	0.042*
H10B	0.2789	0.0828	0.3322	0.042*
C11	0.1170 (3)	0.0792 (2)	0.17141 (19)	0.0317 (4)
C12	0.6510 (5)	0.3118 (4)	0.0971 (3)	0.0624 (8)
H12	0.5284	0.2565	0.0581	0.075*
C13	0.7450 (8)	0.2152 (6)	0.0605 (5)	0.124 (2)
H13A	0.7367	0.1960	−0.0388	0.186*
H13B	0.6925	0.1132	0.1055	0.186*
H13C	0.8683	0.2722	0.0904	0.186*
C14	0.7333 (5)	0.4753 (4)	0.0408 (3)	0.0766 (10)
H14A	0.8535	0.5318	0.0783	0.115*
H14B	0.6652	0.5344	0.0663	0.115*
H14C	0.7351	0.4665	−0.0590	0.115*

	U11	U22	U33	U12	U13	U23
S1	0.0454 (3)	0.0356 (3)	0.0327 (3)	0.0233 (2)	0.0074 (2)	0.00516 (18)
F1	0.0421 (7)	0.0235 (6)	0.0731 (9)	0.0025 (5)	0.0028 (6)	−0.0043 (6)
O1	0.0274 (6)	0.0274 (6)	0.0340 (7)	0.0077 (5)	−0.0037 (5)	0.0021 (5)
O2	0.0785 (12)	0.0260 (7)	0.0413 (8)	0.0041 (7)	−0.0244 (8)	0.0048 (6)
O3	0.0606 (10)	0.0224 (6)	0.0362 (8)	0.0077 (6)	−0.0109 (7)	0.0002 (5)
C1	0.0329 (9)	0.0237 (8)	0.0232 (7)	0.0103 (7)	−0.0018 (6)	−0.0003 (6)
C2	0.0304 (9)	0.0243 (8)	0.0217 (7)	0.0101 (7)	−0.0009 (6)	−0.0001 (6)
C3	0.0278 (9)	0.0277 (8)	0.0334 (9)	0.0082 (7)	0.0014 (7)	−0.0006 (7)
C4	0.0365 (10)	0.0232 (8)	0.0354 (9)	0.0056 (7)	−0.0011 (7)	−0.0015 (7)
C5	0.0436 (11)	0.0269 (8)	0.0353 (9)	0.0164 (8)	0.0006 (8)	−0.0004 (7)
C6	0.0342 (10)	0.0329 (9)	0.0287 (8)	0.0164 (8)	−0.0014 (7)	0.0023 (7)
C7	0.0285 (8)	0.0261 (8)	0.0244 (8)	0.0091 (7)	−0.0034 (6)	0.0013 (6)
C8	0.0324 (9)	0.0243 (8)	0.0259 (8)	0.0088 (7)	−0.0038 (6)	0.0012 (6)
C9	0.0393 (11)	0.0434 (11)	0.0521 (12)	0.0240 (9)	0.0007 (9)	0.0072 (9)
C10	0.0392 (10)	0.0245 (8)	0.0326 (9)	0.0057 (7)	−0.0070 (8)	0.0034 (7)
C11	0.0328 (9)	0.0229 (8)	0.0332 (9)	0.0061 (7)	−0.0037 (7)	0.0015 (6)
C12	0.097 (2)	0.0646 (16)	0.0406 (12)	0.0479 (16)	0.0232 (13)	0.0050 (11)
C13	0.202 (6)	0.151 (4)	0.086 (3)	0.135 (5)	0.063 (3)	0.026 (3)
C14	0.116 (3)	0.076 (2)	0.0474 (15)	0.048 (2)	0.0261 (16)	0.0178 (14)

S1—C1	1.7464 (19)	C6—C9	1.502 (3)
S1—C12	1.847 (3)	C8—C10	1.485 (2)
F1—C4	1.365 (2)	C9—H9A	0.9800
O1—C8	1.368 (2)	C9—H9B	0.9800
O1—C7	1.376 (2)	C9—H9C	0.9800
O2—C11	1.217 (2)	C10—C11	1.506 (3)
O3—C11	1.295 (2)	C10—H10A	0.9900
O3—H3O	0.86 (4)	C10—H10B	0.9900
C1—C8	1.352 (3)	C12—C13	1.469 (4)
C1—C2	1.446 (2)	C12—C14	1.501 (4)
C2—C7	1.390 (3)	C12—H12	1.0000
C2—C3	1.395 (2)	C13—H13A	0.9800
C3—C4	1.375 (3)	C13—H13B	0.9800
C3—H3	0.9500	C13—H13C	0.9800
C4—C5	1.387 (3)	C14—H14A	0.9800
C5—C6	1.387 (3)	C14—H14B	0.9800
C5—H5	0.9500	C14—H14C	0.9800
C6—C7	1.390 (3)
C1—S1—C12	101.58 (11)	C6—C9—H9C	109.5
C8—O1—C7	105.60 (14)	H9A—C9—H9C	109.5
C11—O3—H3O	110 (3)	H9B—C9—H9C	109.5
C8—C1—C2	105.76 (16)	C8—C10—C11	113.50 (15)
C8—C1—S1	125.54 (14)	C8—C10—H10A	108.9
C2—C1—S1	128.66 (14)	C11—C10—H10A	108.9
C7—C2—C3	119.79 (16)	C8—C10—H10B	108.9
C7—C2—C1	105.53 (15)	C11—C10—H10B	108.9
C3—C2—C1	134.68 (17)	H10A—C10—H10B	107.7
C4—C3—C2	115.14 (17)	O2—C11—O3	123.96 (17)
C4—C3—H3	122.4	O2—C11—C10	122.48 (16)
C2—C3—H3	122.4	O3—C11—C10	113.55 (16)
F1—C4—C3	118.24 (18)	C13—C12—C14	112.4 (3)
F1—C4—C5	116.81 (17)	C13—C12—S1	107.5 (2)
C3—C4—C5	124.94 (17)	C14—C12—S1	112.2 (2)
C4—C5—C6	120.63 (17)	C13—C12—H12	108.2
C4—C5—H5	119.7	C14—C12—H12	108.2
C6—C5—H5	119.7	S1—C12—H12	108.2
C5—C6—C7	114.44 (17)	C12—C13—H13A	109.5
C5—C6—C9	123.24 (18)	C12—C13—H13B	109.5
C7—C6—C9	122.32 (18)	H13A—C13—H13B	109.5
O1—C7—C2	110.54 (15)	C12—C13—H13C	109.5
O1—C7—C6	124.41 (17)	H13A—C13—H13C	109.5
C2—C7—C6	125.04 (17)	H13B—C13—H13C	109.5
C1—C8—O1	112.56 (15)	C12—C14—H14A	109.5
C1—C8—C10	130.95 (18)	C12—C14—H14B	109.5
O1—C8—C10	116.49 (16)	H14A—C14—H14B	109.5
C6—C9—H9A	109.5	C12—C14—H14C	109.5
C6—C9—H9B	109.5	H14A—C14—H14C	109.5
H9A—C9—H9B	109.5	H14B—C14—H14C	109.5
C12—S1—C1—C8	91.91 (19)	C3—C2—C7—C6	1.5 (3)
C12—S1—C1—C2	−91.00 (18)	C1—C2—C7—C6	−178.68 (16)
C8—C1—C2—C7	−0.86 (19)	C5—C6—C7—O1	179.41 (16)
S1—C1—C2—C7	−178.39 (13)	C9—C6—C7—O1	−0.6 (3)
C8—C1—C2—C3	178.94 (19)	C5—C6—C7—C2	−1.0 (3)
S1—C1—C2—C3	1.4 (3)	C9—C6—C7—C2	179.04 (18)
C7—C2—C3—C4	−0.7 (3)	C2—C1—C8—O1	0.5 (2)
C1—C2—C3—C4	179.49 (18)	S1—C1—C8—O1	178.10 (12)
C2—C3—C4—F1	178.68 (16)	C2—C1—C8—C10	−179.33 (17)
C2—C3—C4—C5	−0.4 (3)	S1—C1—C8—C10	−1.7 (3)
F1—C4—C5—C6	−178.20 (17)	C7—O1—C8—C1	0.13 (19)
C3—C4—C5—C6	0.9 (3)	C7—O1—C8—C10	179.95 (14)
C4—C5—C6—C7	−0.2 (3)	C1—C8—C10—C11	−98.2 (2)
C4—C5—C6—C9	179.80 (19)	O1—C8—C10—C11	82.0 (2)
C8—O1—C7—C2	−0.71 (18)	C8—C10—C11—O2	−5.3 (3)
C8—O1—C7—C6	178.95 (16)	C8—C10—C11—O3	174.37 (18)
C3—C2—C7—O1	−178.85 (15)	C1—S1—C12—C13	−168.1 (3)
C1—C2—C7—O1	0.98 (19)	C1—S1—C12—C14	67.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2i	0.86 (4)	1.76 (4)	2.616 (2)	176 (4)
C9—H9B···O3ii	0.98	2.56	3.534 (3)	171

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2i	0.86 (4)	1.76 (4)	2.616 (2)	176 (4)
C9—H9B⋯O3ii	0.98	2.56	3.534 (3)	171

Symmetry codes: (i) ; (ii) .