2-(5-Bromo-3-isopropyl-sulfanyl-1-benzofuran-2-yl)acetic acid.

The title compound, C(13)H(13)BrO(3)S, was prepared by alkaline hydrolysis of ethyl 2-(5-bromo-3-isopropyl-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 dimers. These dimers are further packed into stacks along the c axis by inter-molecular C-H⋯π inter-actions, and by slipped π-π inter-actions between the furan rings of adjacent mol-ecules [centroid-centroid distance = 3.472 (2) Å, inter-planar distance = 3.398 (2) Å and slippage = 0.713 (2) Å].

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 the crystal structures of related compounds, see: Choi et al. (2009 ▶).

Experimental

Crystal data

C13H13BrO3S

M = 329.20

Triclinic,

a = 7.4689 (3) Å

b = 9.9449 (4) Å

c = 10.0653 (4) Å

α = 98.415 (2)°

β = 102.146 (2)°

γ = 110.341 (3)°

V = 665.38 (5) Å3

Z = 2

Mo Kα radiation

μ = 3.24 mm−1

T = 296 K

0.24 × 0.17 × 0.10 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.510, T max = 0.738

11869 measured reflections

3082 independent reflections

2731 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.024

wR(F 2) = 0.064

S = 1.03

3082 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.52 e Å−3

Δρmin = −0.30 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/S1600536811052160/bg2430sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811052160/bg2430Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811052160/bg2430Isup3.cml

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

C13H13BrO3S	Z = 2
Mr = 329.20	F(000) = 332
Triclinic, P1	Dx = 1.643 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.4689 (3) Å	Cell parameters from 5830 reflections
b = 9.9449 (4) Å	θ = 2.3–27.5°
c = 10.0653 (4) Å	µ = 3.24 mm−1
α = 98.415 (2)°	T = 296 K
β = 102.146 (2)°	Block, colourless
γ = 110.341 (3)°	0.24 × 0.17 × 0.10 mm
V = 665.38 (5) Å3

Bruker SMART APEXII CCD diffractometer	3082 independent reflections
Radiation source: rotating anode	2731 reflections with I > 2σ(I)
graphite multilayer	Rint = 0.030
Detector resolution: 10.0 pixels mm-1	θmax = 27.6°, θmin = 2.1°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −12→12
Tmin = 0.510, Tmax = 0.738	l = −13→13
11869 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)] = 0.024	Hydrogen site location: difference Fourier map
wR(F2) = 0.064	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0351P)2 + 0.1792P] where P = (Fo2 + 2Fc2)/3
3082 reflections	(Δ/σ)max = 0.001
169 parameters	Δρmax = 0.52 e Å−3
0 restraints	Δρmin = −0.30 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
Br1	0.19969 (3)	−0.066508 (19)	0.14451 (2)	0.03256 (8)
S1	0.19347 (6)	0.56388 (5)	0.18733 (4)	0.02002 (10)
O1	0.71390 (18)	0.55476 (13)	0.17068 (13)	0.0206 (2)
O2	0.8525 (2)	1.01742 (15)	0.34019 (17)	0.0322 (3)
H2O	0.925 (4)	1.059 (3)	0.409 (3)	0.050 (9)*
O3	0.8861 (2)	0.82564 (14)	0.41728 (14)	0.0290 (3)
C1	0.4055 (2)	0.52528 (18)	0.18780 (17)	0.0180 (3)
C2	0.4198 (2)	0.38295 (18)	0.17355 (17)	0.0176 (3)
C3	0.2914 (3)	0.24052 (18)	0.16819 (18)	0.0196 (3)
H3	0.1627	0.2202	0.1749	0.024*
C4	0.3645 (3)	0.13091 (19)	0.15246 (18)	0.0213 (3)
C5	0.5565 (3)	0.1574 (2)	0.14170 (19)	0.0227 (4)
H5	0.5989	0.0799	0.1316	0.027*
C6	0.6840 (3)	0.2986 (2)	0.14606 (19)	0.0223 (4)
H6	0.8119	0.3185	0.1379	0.027*
C7	0.6116 (2)	0.40805 (18)	0.16307 (17)	0.0190 (3)
C8	0.5840 (3)	0.62221 (18)	0.18556 (17)	0.0184 (3)
C9	0.6588 (3)	0.78314 (18)	0.19365 (18)	0.0207 (3)
H9A	0.5471	0.8131	0.1809	0.025*
H9B	0.7170	0.8019	0.1172	0.025*
C10	0.8114 (3)	0.87651 (19)	0.32922 (19)	0.0210 (3)
C11	0.2061 (3)	0.6058 (2)	0.37390 (19)	0.0252 (4)
H11	0.0865	0.6237	0.3795	0.030*
C12	0.3829 (3)	0.7457 (2)	0.4566 (2)	0.0377 (5)
H12A	0.3768	0.7682	0.5511	0.056*
H12B	0.3803	0.8259	0.4144	0.056*
H12C	0.5038	0.7317	0.4565	0.056*
C13	0.1986 (3)	0.4754 (2)	0.4379 (2)	0.0326 (4)
H13A	0.3110	0.4516	0.4314	0.049*
H13B	0.0780	0.3916	0.3882	0.049*
H13C	0.2020	0.5004	0.5344	0.049*

	U11	U22	U33	U12	U13	U23
Br1	0.03694 (13)	0.01654 (10)	0.04563 (14)	0.00761 (8)	0.01796 (10)	0.00961 (8)
S1	0.0193 (2)	0.0200 (2)	0.0201 (2)	0.00800 (17)	0.00334 (17)	0.00490 (16)
O1	0.0187 (6)	0.0170 (6)	0.0213 (6)	0.0032 (5)	0.0045 (5)	0.0012 (5)
O2	0.0399 (8)	0.0150 (6)	0.0274 (8)	0.0067 (6)	−0.0091 (7)	−0.0003 (5)
O3	0.0344 (7)	0.0161 (6)	0.0251 (7)	0.0052 (6)	−0.0054 (6)	0.0028 (5)
C1	0.0203 (8)	0.0175 (8)	0.0139 (8)	0.0061 (7)	0.0033 (6)	0.0025 (6)
C2	0.0196 (8)	0.0176 (8)	0.0125 (8)	0.0058 (7)	0.0024 (6)	0.0012 (6)
C3	0.0208 (8)	0.0190 (8)	0.0179 (8)	0.0061 (7)	0.0063 (7)	0.0041 (6)
C4	0.0249 (9)	0.0168 (8)	0.0186 (9)	0.0049 (7)	0.0051 (7)	0.0035 (6)
C5	0.0270 (9)	0.0209 (8)	0.0203 (9)	0.0119 (7)	0.0041 (7)	0.0025 (7)
C6	0.0190 (8)	0.0246 (9)	0.0205 (9)	0.0077 (7)	0.0043 (7)	0.0011 (7)
C7	0.0193 (8)	0.0189 (8)	0.0137 (8)	0.0034 (7)	0.0028 (6)	0.0013 (6)
C8	0.0214 (8)	0.0177 (8)	0.0134 (8)	0.0065 (7)	0.0027 (7)	0.0015 (6)
C9	0.0220 (8)	0.0160 (8)	0.0183 (9)	0.0026 (7)	0.0029 (7)	0.0032 (6)
C10	0.0215 (8)	0.0161 (8)	0.0217 (9)	0.0041 (7)	0.0051 (7)	0.0027 (6)
C11	0.0270 (9)	0.0309 (10)	0.0212 (9)	0.0140 (8)	0.0094 (8)	0.0056 (7)
C12	0.0431 (12)	0.0360 (12)	0.0241 (11)	0.0091 (10)	0.0077 (9)	−0.0030 (8)
C13	0.0361 (11)	0.0423 (12)	0.0268 (10)	0.0185 (10)	0.0136 (9)	0.0148 (9)

Br1—C4	1.8996 (17)	C5—H5	0.9300
S1—C1	1.7533 (17)	C6—C7	1.378 (2)
S1—C11	1.8380 (18)	C6—H6	0.9300
O1—C7	1.373 (2)	C8—C9	1.484 (2)
O1—C8	1.378 (2)	C9—C10	1.504 (2)
O2—C10	1.308 (2)	C9—H9A	0.9700
O2—H2O	0.74 (3)	C9—H9B	0.9700
O3—C10	1.213 (2)	C11—C12	1.515 (3)
C1—C8	1.354 (2)	C11—C13	1.519 (3)
C1—C2	1.445 (2)	C11—H11	0.9800
C2—C3	1.393 (2)	C12—H12A	0.9600
C2—C7	1.396 (2)	C12—H12B	0.9600
C3—C4	1.382 (2)	C12—H12C	0.9600
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.396 (3)	C13—H13B	0.9600
C5—C6	1.383 (3)	C13—H13C	0.9600
C1—S1—C11	103.26 (8)	C8—C9—C10	114.05 (14)
C7—O1—C8	105.80 (12)	C8—C9—H9A	108.7
C10—O2—H2O	108 (2)	C10—C9—H9A	108.7
C8—C1—C2	106.08 (14)	C8—C9—H9B	108.7
C8—C1—S1	125.91 (13)	C10—C9—H9B	108.7
C2—C1—S1	127.62 (13)	H9A—C9—H9B	107.6
C3—C2—C7	119.53 (15)	O3—C10—O2	124.59 (17)
C3—C2—C1	134.93 (15)	O3—C10—C9	123.37 (16)
C7—C2—C1	105.53 (14)	O2—C10—C9	112.04 (15)
C4—C3—C2	116.75 (15)	C12—C11—C13	112.01 (17)
C4—C3—H3	121.6	C12—C11—S1	112.33 (13)
C2—C3—H3	121.6	C13—C11—S1	111.88 (13)
C3—C4—C5	123.14 (16)	C12—C11—H11	106.7
C3—C4—Br1	119.60 (13)	C13—C11—H11	106.7
C5—C4—Br1	117.26 (13)	S1—C11—H11	106.7
C6—C5—C4	120.26 (16)	C11—C12—H12A	109.5
C6—C5—H5	119.9	C11—C12—H12B	109.5
C4—C5—H5	119.9	H12A—C12—H12B	109.5
C7—C6—C5	116.58 (16)	C11—C12—H12C	109.5
C7—C6—H6	121.7	H12A—C12—H12C	109.5
C5—C6—H6	121.7	H12B—C12—H12C	109.5
O1—C7—C6	125.78 (15)	C11—C13—H13A	109.5
O1—C7—C2	110.49 (14)	C11—C13—H13B	109.5
C6—C7—C2	123.73 (16)	H13A—C13—H13B	109.5
C1—C8—O1	112.10 (14)	C11—C13—H13C	109.5
C1—C8—C9	131.51 (16)	H13A—C13—H13C	109.5
O1—C8—C9	116.38 (14)	H13B—C13—H13C	109.5
C11—S1—C1—C8	−95.71 (16)	C3—C2—C7—O1	−179.98 (14)
C11—S1—C1—C2	92.46 (16)	C1—C2—C7—O1	0.32 (18)
C8—C1—C2—C3	−179.91 (18)	C3—C2—C7—C6	0.6 (3)
S1—C1—C2—C3	−6.8 (3)	C1—C2—C7—C6	−179.08 (16)
C8—C1—C2—C7	−0.27 (18)	C2—C1—C8—O1	0.13 (19)
S1—C1—C2—C7	172.85 (13)	S1—C1—C8—O1	−173.14 (12)
C7—C2—C3—C4	0.0 (2)	C2—C1—C8—C9	178.91 (17)
C1—C2—C3—C4	179.61 (18)	S1—C1—C8—C9	5.6 (3)
C2—C3—C4—C5	−0.2 (3)	C7—O1—C8—C1	0.06 (18)
C2—C3—C4—Br1	179.88 (12)	C7—O1—C8—C9	−178.91 (14)
C3—C4—C5—C6	−0.2 (3)	C1—C8—C9—C10	109.0 (2)
Br1—C4—C5—C6	179.71 (13)	O1—C8—C9—C10	−72.23 (19)
C4—C5—C6—C7	0.8 (3)	C8—C9—C10—O3	8.9 (3)
C8—O1—C7—C6	179.14 (17)	C8—C9—C10—O2	−170.96 (15)
C8—O1—C7—C2	−0.24 (17)	C1—S1—C11—C12	66.06 (16)
C5—C6—C7—O1	179.67 (16)	C1—S1—C11—C13	−60.93 (15)
C5—C6—C7—C2	−1.0 (3)

Cg2 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2O···O3i	0.74 (3)	1.90 (3)	2.640 (2)	177 (3)
C9—H9B···Cg2ii	0.97	2.72 (1)	3.376 (2)	126.

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2O⋯O3i	0.74 (3)	1.90 (3)	2.640 (2)	177 (3)
C9—H9B⋯Cg2ii	0.97	2.72 (1)	3.376 (2)	126

Symmetry codes: (i) ; (ii) .