2-(5-Bromo-3-methyl-sulfinyl-1-benzofuran-2-yl)acetic acid.

In the title compound, C(11)H(9)BrO(4)S, the O atom and the methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran fragment. The crystal structure is stabilized by inter-molecular O-H⋯O and C-H⋯O inter-actions. In addition, the crystal structure exhibits a Br⋯π inter-action of 3.551 (3) Å between the Br atom and the centroid of the benzene ring of an adjacent mol-ecule.

Related literature

For the crystal structures of similar 2-(5-bromo-3-methyl­sulfinyl-1-benzofuran-2-yl)acetic acid derivatives, see: Choi et al. (2008 ▶, 2009 ▶).

Experimental

Crystal data

C11H9BrO4S

M = 317.15

Orthorhombic,

a = 7.7646 (7) Å

b = 16.304 (2) Å

c = 18.993 (2) Å

V = 2404.4 (4) Å3

Z = 8

Mo Kα radiation

μ = 3.59 mm−1

T = 298 K

0.60 × 0.60 × 0.40 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.130, T max = 0.233

13628 measured reflections

2621 independent reflections

2033 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.094

S = 1.05

2621 reflections

160 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.36 e Å−3

Δρmin = −0.85 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/S1600536809008101/zl2184sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008101/zl2184Isup2.hkl

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

C11H9BrO4S	F(000) = 1264
Mr = 317.15	Dx = 1.752 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4375 reflections
a = 7.7646 (7) Å	θ = 2.5–26.9°
b = 16.304 (2) Å	µ = 3.59 mm−1
c = 18.993 (2) Å	T = 298 K
V = 2404.4 (4) Å3	Block, colorless
Z = 8	0.60 × 0.60 × 0.40 mm

Bruker SMART CCD diffractometer	2621 independent reflections
Radiation source: fine-focus sealed tube	2033 reflections with I > 2σ(I)
graphite	Rint = 0.030
Detector resolution: 10.0 pixels mm-1	θmax = 27.0°, θmin = 2.1°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −17→20
Tmin = 0.130, Tmax = 0.233	l = −22→24
13628 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)] = 0.036	Hydrogen site location: difference Fourier map
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0414P)2 + 2.2996P] where P = (Fo2 + 2Fc2)/3
2621 reflections	(Δ/σ)max = 0.001
160 parameters	Δρmax = 0.36 e Å−3
0 restraints	Δρmin = −0.85 e Å−3

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
Br	0.09253 (6)	0.55548 (3)	0.70463 (2)	0.07726 (18)
S	0.61529 (8)	0.28188 (4)	0.61833 (4)	0.03288 (16)
O1	0.7445 (2)	0.49916 (11)	0.54672 (9)	0.0373 (4)
O2	1.1855 (3)	0.32375 (15)	0.53576 (12)	0.0489 (6)
H2A	1.252 (5)	0.306 (2)	0.5603 (19)	0.057 (12)*
O3	1.0177 (3)	0.32808 (17)	0.62986 (11)	0.0634 (7)
O4	0.4277 (2)	0.26028 (12)	0.61107 (13)	0.0511 (6)
C1	0.6340 (3)	0.38564 (15)	0.59570 (13)	0.0296 (5)
C2	0.5212 (3)	0.45323 (15)	0.61355 (13)	0.0290 (5)
C3	0.3678 (3)	0.46237 (16)	0.65037 (14)	0.0340 (6)
H3	0.3126	0.4179	0.6711	0.041*
C4	0.3016 (4)	0.54037 (17)	0.65473 (14)	0.0380 (6)
C5	0.3810 (4)	0.60866 (17)	0.62502 (14)	0.0402 (6)
H5	0.3322	0.6603	0.6306	0.048*
C6	0.5312 (4)	0.60005 (17)	0.58753 (15)	0.0398 (6)
H6	0.5857	0.6446	0.5667	0.048*
C7	0.5968 (3)	0.52154 (17)	0.58250 (14)	0.0328 (5)
C8	0.7617 (3)	0.41652 (16)	0.55538 (13)	0.0321 (6)
C9	0.9129 (3)	0.37869 (18)	0.51972 (15)	0.0386 (6)
H9A	0.9696	0.4202	0.4914	0.046*
H9B	0.8723	0.3362	0.4881	0.046*
C10	1.0426 (3)	0.34198 (16)	0.56920 (14)	0.0343 (6)
C11	0.6508 (4)	0.2897 (2)	0.71079 (15)	0.0524 (8)
H11A	0.5754	0.3305	0.7302	0.079*
H11B	0.7683	0.3050	0.7194	0.079*
H11C	0.6278	0.2377	0.7326	0.079*

	U11	U22	U33	U12	U13	U23
Br	0.0694 (3)	0.0723 (3)	0.0901 (3)	0.0299 (2)	0.0476 (2)	0.0178 (2)
S	0.0288 (3)	0.0292 (3)	0.0406 (4)	0.0017 (3)	−0.0038 (3)	0.0007 (3)
O1	0.0305 (9)	0.0365 (10)	0.0447 (10)	−0.0004 (8)	0.0068 (8)	0.0059 (8)
O2	0.0321 (11)	0.0708 (15)	0.0437 (12)	0.0153 (10)	0.0048 (10)	0.0039 (11)
O3	0.0390 (12)	0.109 (2)	0.0421 (13)	0.0163 (13)	0.0062 (10)	0.0189 (12)
O4	0.0328 (11)	0.0399 (11)	0.0808 (16)	−0.0076 (9)	−0.0157 (10)	0.0114 (11)
C1	0.0264 (12)	0.0309 (13)	0.0315 (12)	−0.0004 (10)	−0.0016 (10)	−0.0007 (10)
C2	0.0292 (12)	0.0289 (12)	0.0288 (12)	0.0004 (10)	−0.0018 (10)	0.0008 (10)
C3	0.0318 (14)	0.0356 (14)	0.0346 (14)	0.0005 (11)	0.0045 (11)	0.0029 (11)
C4	0.0351 (15)	0.0472 (17)	0.0317 (14)	0.0101 (12)	0.0068 (11)	0.0007 (12)
C5	0.0464 (16)	0.0339 (14)	0.0404 (15)	0.0110 (12)	0.0005 (12)	0.0010 (12)
C6	0.0443 (16)	0.0309 (14)	0.0443 (16)	−0.0001 (12)	0.0012 (13)	0.0062 (12)
C7	0.0284 (13)	0.0365 (14)	0.0334 (13)	−0.0001 (11)	0.0013 (10)	0.0016 (11)
C8	0.0289 (13)	0.0342 (13)	0.0333 (14)	0.0047 (10)	−0.0007 (10)	0.0006 (10)
C9	0.0325 (14)	0.0473 (16)	0.0360 (14)	0.0075 (12)	0.0039 (11)	0.0009 (12)
C10	0.0274 (13)	0.0380 (14)	0.0375 (15)	−0.0020 (11)	0.0023 (11)	−0.0014 (12)
C11	0.0490 (18)	0.068 (2)	0.0403 (16)	−0.0029 (16)	−0.0024 (14)	0.0116 (15)

Br—C4	1.896 (3)	C3—H3	0.9300
S—O4	1.5051 (19)	C4—C5	1.392 (4)
S—C1	1.752 (3)	C5—C6	1.374 (4)
S—C11	1.782 (3)	C5—H5	0.9300
O1—C8	1.364 (3)	C6—C7	1.381 (4)
O1—C7	1.382 (3)	C6—H6	0.9300
O2—C10	1.313 (3)	C8—C9	1.490 (3)
O2—H2A	0.76 (4)	C9—C10	1.502 (4)
O3—C10	1.190 (3)	C9—H9A	0.9700
C1—C8	1.350 (3)	C9—H9B	0.9700
C1—C2	1.448 (3)	C11—H11A	0.9600
C2—C3	1.389 (4)	C11—H11B	0.9600
C2—C7	1.391 (4)	C11—H11C	0.9600
C3—C4	1.374 (4)
O4—S—C1	106.49 (12)	C7—C6—H6	121.8
O4—S—C11	104.87 (15)	C6—C7—O1	125.8 (2)
C1—S—C11	99.22 (15)	C6—C7—C2	123.9 (2)
C8—O1—C7	106.42 (19)	O1—C7—C2	110.4 (2)
C10—O2—H2A	112 (3)	C1—C8—O1	111.4 (2)
C8—C1—C2	107.1 (2)	C1—C8—C9	133.0 (3)
C8—C1—S	124.1 (2)	O1—C8—C9	115.5 (2)
C2—C1—S	128.86 (19)	C8—C9—C10	114.1 (2)
C3—C2—C7	119.3 (2)	C8—C9—H9A	108.7
C3—C2—C1	135.9 (2)	C10—C9—H9A	108.7
C7—C2—C1	104.7 (2)	C8—C9—H9B	108.7
C4—C3—C2	116.8 (2)	C10—C9—H9B	108.7
C4—C3—H3	121.6	H9A—C9—H9B	107.6
C2—C3—H3	121.6	O3—C10—O2	124.3 (3)
C3—C4—C5	123.4 (2)	O3—C10—C9	124.9 (3)
C3—C4—Br	118.1 (2)	O2—C10—C9	110.7 (2)
C5—C4—Br	118.6 (2)	S—C11—H11A	109.5
C6—C5—C4	120.3 (3)	S—C11—H11B	109.5
C6—C5—H5	119.9	H11A—C11—H11B	109.5
C4—C5—H5	119.9	S—C11—H11C	109.5
C5—C6—C7	116.4 (3)	H11A—C11—H11C	109.5
C5—C6—H6	121.8	H11B—C11—H11C	109.5
O4—S—C1—C8	−137.7 (2)	C8—O1—C7—C6	179.9 (3)
C11—S—C1—C8	113.7 (2)	C8—O1—C7—C2	−0.1 (3)
O4—S—C1—C2	40.9 (3)	C3—C2—C7—C6	2.0 (4)
C11—S—C1—C2	−67.7 (3)	C1—C2—C7—C6	−179.0 (3)
C8—C1—C2—C3	177.3 (3)	C3—C2—C7—O1	−178.1 (2)
S—C1—C2—C3	−1.5 (5)	C1—C2—C7—O1	0.9 (3)
C8—C1—C2—C7	−1.5 (3)	C2—C1—C8—O1	1.5 (3)
S—C1—C2—C7	179.8 (2)	S—C1—C8—O1	−179.63 (18)
C7—C2—C3—C4	−1.2 (4)	C2—C1—C8—C9	−178.5 (3)
C1—C2—C3—C4	−179.8 (3)	S—C1—C8—C9	0.4 (4)
C2—C3—C4—C5	−0.6 (4)	C7—O1—C8—C1	−0.9 (3)
C2—C3—C4—Br	−179.94 (19)	C7—O1—C8—C9	179.1 (2)
C3—C4—C5—C6	1.7 (4)	C1—C8—C9—C10	−64.2 (4)
Br—C4—C5—C6	−179.0 (2)	O1—C8—C9—C10	115.8 (3)
C4—C5—C6—C7	−0.9 (4)	C8—C9—C10—O3	14.6 (4)
C5—C6—C7—O1	179.2 (2)	C8—C9—C10—O2	−168.3 (2)
C5—C6—C7—C2	−0.9 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O4i	0.76 (4)	1.83 (4)	2.579 (3)	174 (4)
C5—H5···O4ii	0.93	2.62	3.453 (3)	150
C6—H6···O2iii	0.93	2.68	3.444 (4)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O4i	0.76 (4)	1.83 (4)	2.579 (3)	174 (4)
C5—H5⋯O4ii	0.93	2.62	3.453 (3)	150
C6—H6⋯O2iii	0.93	2.68	3.444 (4)	140

Symmetry codes: (i) ; (ii) ; (iii) .