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

The title compound, C(13)H(14)O(3)S, was prepared by alkaline hydrolysis of ethyl 2-(5,7-dimethyl-3-methyl-sulfanyl-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 a axis by weak C-H⋯π inter-actions.

Related literature

For the crystal structures of similar 2-(3-methyl­sulfanyl-1-benzofuran-2-yl)acetic acid derivatives, see: Choi et al. (2007 ▶); Seo et al. (2007 ▶).

Experimental

Crystal data

C13H14O3S

M = 250.30

Triclinic,

a = 4.7225 (9) Å

b = 7.476 (2) Å

c = 17.687 (3) Å

α = 80.91 (3)°

β = 89.86 (3)°

γ = 80.67 (3)°

V = 608.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 293 (2) K

0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

4707 measured reflections

2344 independent reflections

2156 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.144

S = 1.24

2344 reflections

161 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.38 e Å−3

Δρmin = −0.41 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/S1600536808022988/cv2433sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808022988/cv2433Isup2.hkl

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

C13H14O3S	Z = 2
Mr = 250.30	F000 = 264
Triclinic, P1	Dx = 1.367 Mg m−3
Hall symbol: -P_1	Melting point = 420–421 K
a = 4.7225 (9) Å	Mo Kα radiation λ = 0.71073 Å
b = 7.476 (2) Å	Cell parameters from 3835 reflections
c = 17.687 (3) Å	θ = 2.3–28.3º
α = 80.91 (3)º	µ = 0.26 mm−1
β = 89.86 (3)º	T = 293 (2) K
γ = 80.67 (3)º	Block, colourless
V = 608.3 (2) Å3	0.40 × 0.40 × 0.20 mm

Bruker SMART CCD diffractometer	2344 independent reflections
Radiation source: fine-focus sealed tube	2156 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.059
Detector resolution: 10.0 pixels mm-1	θmax = 26.0º
T = 293(2) K	θmin = 1.2º
φ and ω scans	h = −5→5
Absorption correction: none	k = −9→9
4707 measured reflections	l = −21→21

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.047	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.144	w = 1/[σ2(Fo2) + (0.063P)2 + 0.3562P] where P = (Fo2 + 2Fc2)/3
S = 1.24	(Δ/σ)max < 0.001
2344 reflections	Δρmax = 0.38 e Å−3
161 parameters	Δρmin = −0.41 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	0.85977 (13)	0.34264 (8)	0.36615 (3)	0.0254 (2)
O1	0.4166 (3)	0.8236 (2)	0.27417 (9)	0.0223 (4)
O2	0.2357 (4)	0.9616 (2)	0.44893 (10)	0.0272 (4)
O3	0.6544 (4)	0.7728 (2)	0.47532 (11)	0.0282 (4)
H3O	0.685 (8)	0.848 (5)	0.494 (2)	0.049 (11)*
C1	0.6982 (5)	0.5473 (3)	0.30908 (14)	0.0214 (5)
C2	0.7803 (5)	0.6242 (3)	0.23378 (14)	0.0232 (5)
C3	0.9867 (5)	0.5690 (3)	0.18203 (15)	0.0268 (5)
H3	1.1098	0.4574	0.1936	0.032*
C4	1.0055 (6)	0.6834 (4)	0.11284 (15)	0.0293 (6)
C5	0.8179 (6)	0.8526 (3)	0.09713 (15)	0.0306 (6)
H5	0.8332	0.9275	0.0505	0.037*
C6	0.6115 (6)	0.9133 (3)	0.14758 (15)	0.0279 (5)
C7	0.6010 (5)	0.7931 (3)	0.21521 (14)	0.0231 (5)
C8	0.4821 (5)	0.6706 (3)	0.32972 (13)	0.0211 (5)
C9	1.2248 (6)	0.6283 (4)	0.05502 (17)	0.0400 (7)
H9A	1.4113	0.6436	0.0718	0.060*
H9B	1.1762	0.7043	0.0063	0.060*
H9C	1.2265	0.5021	0.0502	0.060*
C10	0.4134 (6)	1.0944 (3)	0.13076 (17)	0.0359 (6)
H10A	0.2325	1.0833	0.1544	0.054*
H10B	0.3842	1.1291	0.0764	0.054*
H10C	0.4972	1.1864	0.1508	0.054*
C11	0.3130 (5)	0.6760 (3)	0.40038 (13)	0.0225 (5)
H11A	0.3482	0.5562	0.4324	0.027*
H11B	0.1099	0.7050	0.3869	0.027*
C12	0.3944 (5)	0.8187 (3)	0.44444 (13)	0.0195 (5)
C13	0.7336 (6)	0.1752 (3)	0.31692 (18)	0.0360 (6)
H13A	0.5277	0.1920	0.3176	0.054*
H13B	0.8110	0.0538	0.3421	0.054*
H13C	0.7950	0.1908	0.2649	0.054*

	U11	U22	U33	U12	U13	U23
S	0.0300 (3)	0.0185 (3)	0.0271 (3)	−0.0028 (2)	−0.0065 (2)	−0.0025 (2)
O1	0.0275 (8)	0.0163 (7)	0.0230 (9)	−0.0025 (6)	0.0001 (6)	−0.0039 (6)
O2	0.0275 (9)	0.0214 (8)	0.0334 (10)	−0.0003 (7)	−0.0053 (7)	−0.0105 (7)
O3	0.0251 (9)	0.0248 (9)	0.0370 (10)	−0.0017 (7)	−0.0069 (7)	−0.0140 (8)
C1	0.0254 (11)	0.0162 (10)	0.0241 (12)	−0.0044 (8)	−0.0027 (9)	−0.0063 (9)
C2	0.0256 (12)	0.0200 (11)	0.0263 (12)	−0.0079 (9)	−0.0025 (9)	−0.0066 (9)
C3	0.0267 (12)	0.0261 (12)	0.0297 (13)	−0.0068 (9)	0.0006 (10)	−0.0084 (10)
C4	0.0334 (13)	0.0314 (13)	0.0289 (13)	−0.0150 (10)	0.0057 (10)	−0.0125 (10)
C5	0.0418 (15)	0.0292 (13)	0.0235 (13)	−0.0155 (11)	0.0006 (10)	−0.0024 (10)
C6	0.0366 (13)	0.0209 (11)	0.0281 (13)	−0.0092 (10)	−0.0021 (10)	−0.0051 (10)
C7	0.0280 (12)	0.0209 (11)	0.0227 (12)	−0.0074 (9)	−0.0006 (9)	−0.0066 (9)
C8	0.0256 (11)	0.0170 (10)	0.0223 (11)	−0.0066 (8)	−0.0045 (9)	−0.0045 (9)
C9	0.0449 (16)	0.0437 (16)	0.0368 (15)	−0.0173 (13)	0.0140 (13)	−0.0125 (13)
C10	0.0480 (16)	0.0247 (13)	0.0318 (14)	−0.0035 (11)	−0.0049 (12)	0.0031 (11)
C11	0.0252 (11)	0.0191 (10)	0.0253 (12)	−0.0074 (9)	0.0000 (9)	−0.0059 (9)
C12	0.0218 (11)	0.0188 (10)	0.0193 (11)	−0.0071 (8)	0.0025 (8)	−0.0035 (8)
C13	0.0439 (15)	0.0200 (11)	0.0452 (16)	−0.0068 (11)	−0.0132 (12)	−0.0066 (11)

S—C1	1.755 (2)	C5—H5	0.9300
S—C13	1.808 (3)	C6—C7	1.384 (4)
O1—C8	1.379 (3)	C6—C10	1.503 (4)
O1—C7	1.380 (3)	C8—C11	1.484 (3)
O2—C12	1.215 (3)	C9—H9A	0.9600
O3—C12	1.316 (3)	C9—H9B	0.9600
O3—H3O	0.73 (4)	C9—H9C	0.9600
C1—C8	1.351 (3)	C10—H10A	0.9600
C1—C2	1.443 (3)	C10—H10B	0.9600
C2—C7	1.393 (3)	C10—H10C	0.9600
C2—C3	1.394 (3)	C11—C12	1.514 (3)
C3—C4	1.389 (4)	C11—H11A	0.9700
C3—H3	0.9300	C11—H11B	0.9700
C4—C5	1.410 (4)	C13—H13A	0.9600
C4—C9	1.509 (4)	C13—H13B	0.9600
C5—C6	1.390 (4)	C13—H13C	0.9600
C1—S—C13	100.58 (12)	C4—C9—H9A	109.5
C8—O1—C7	105.62 (18)	C4—C9—H9B	109.5
C12—O3—H3O	109 (3)	H9A—C9—H9B	109.5
C8—C1—C2	106.3 (2)	C4—C9—H9C	109.5
C8—C1—S	126.10 (19)	H9A—C9—H9C	109.5
C2—C1—S	127.50 (18)	H9B—C9—H9C	109.5
C7—C2—C3	119.3 (2)	C6—C10—H10A	109.5
C7—C2—C1	105.7 (2)	C6—C10—H10B	109.5
C3—C2—C1	135.1 (2)	H10A—C10—H10B	109.5
C4—C3—C2	118.9 (2)	C6—C10—H10C	109.5
C4—C3—H3	120.6	H10A—C10—H10C	109.5
C2—C3—H3	120.6	H10B—C10—H10C	109.5
C3—C4—C5	119.3 (2)	C8—C11—C12	110.56 (18)
C3—C4—C9	120.6 (3)	C8—C11—H11A	109.5
C5—C4—C9	120.1 (2)	C12—C11—H11A	109.5
C6—C5—C4	123.5 (2)	C8—C11—H11B	109.5
C6—C5—H5	118.3	C12—C11—H11B	109.5
C4—C5—H5	118.3	H11A—C11—H11B	108.1
C7—C6—C5	114.6 (2)	O2—C12—O3	124.3 (2)
C7—C6—C10	122.1 (2)	O2—C12—C11	122.7 (2)
C5—C6—C10	123.3 (2)	O3—C12—C11	112.94 (19)
O1—C7—C6	125.3 (2)	S—C13—H13A	109.5
O1—C7—C2	110.3 (2)	S—C13—H13B	109.5
C6—C7—C2	124.4 (2)	H13A—C13—H13B	109.5
C1—C8—O1	112.1 (2)	S—C13—H13C	109.5
C1—C8—C11	132.8 (2)	H13A—C13—H13C	109.5
O1—C8—C11	115.00 (19)	H13B—C13—H13C	109.5
C13—S—C1—C8	110.5 (2)	C10—C6—C7—O1	−0.8 (4)
C13—S—C1—C2	−74.3 (2)	C5—C6—C7—C2	0.5 (3)
C8—C1—C2—C7	0.2 (2)	C10—C6—C7—C2	−179.7 (2)
S—C1—C2—C7	−175.77 (17)	C3—C2—C7—O1	−178.87 (19)
C8—C1—C2—C3	179.0 (2)	C1—C2—C7—O1	0.2 (2)
S—C1—C2—C3	3.0 (4)	C3—C2—C7—C6	0.1 (3)
C7—C2—C3—C4	−0.7 (3)	C1—C2—C7—C6	179.1 (2)
C1—C2—C3—C4	−179.4 (2)	C2—C1—C8—O1	−0.5 (2)
C2—C3—C4—C5	0.6 (3)	S—C1—C8—O1	175.57 (15)
C2—C3—C4—C9	−179.7 (2)	C2—C1—C8—C11	−177.8 (2)
C3—C4—C5—C6	0.0 (4)	S—C1—C8—C11	−1.8 (4)
C9—C4—C5—C6	−179.6 (2)	C7—O1—C8—C1	0.5 (2)
C4—C5—C6—C7	−0.6 (4)	C7—O1—C8—C11	178.39 (17)
C4—C5—C6—C10	179.6 (2)	C1—C8—C11—C12	108.4 (3)
C8—O1—C7—C6	−179.4 (2)	O1—C8—C11—C12	−68.9 (2)
C8—O1—C7—C2	−0.4 (2)	C8—C11—C12—O2	109.1 (2)
C5—C6—C7—O1	179.4 (2)	C8—C11—C12—O3	−69.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3O···O2i	0.73 (4)	1.95 (4)	2.680 (3)	177 (4)
C9—H9A···Cgii	0.96	2.72	3.621 (4)	156

Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3O⋯O2i	0.73 (4)	1.95 (4)	2.680 (3)	177 (4)
C9—H9A⋯Cgii	0.96	2.72	3.621 (4)	156

Symmetry codes: (i) ; (ii) .