Methyl 2-(5-chloro-3-methyl-sulfinyl-1-benzofuran-2-yl)acetate.

The title compound, C(12)H(11)ClO(4)S, was prepared by the oxidation of methyl 2-(5-chloro-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. 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 aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-to-centroid distance = 3.809 (2) Å], and by C-H⋯π inter-actions between a methyl H atom and the furan ring of an adjacent mol-ecule. In addition, the crystal structure exhibits inter-molecular C-H⋯O hydrogen bonds.

Related literature

For details of the pharmacological activities of benzofuran compounds, see: Ward (1999 ▶). For the crystal structures of similar 2-(3-methyl­sulfinyl-1-benzofuran-2-yl)acetic acid derivatives, see: Choi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C12H11ClO4S

M = 286.72

Triclinic,

a = 7.8910 (5) Å

b = 8.9416 (6) Å

c = 10.4048 (7) Å

α = 73.774 (1)°

β = 78.743 (1)°

γ = 68.559 (1)°

V = 652.55 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.46 mm−1

T = 298 (2) K

0.40 × 0.40 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1999 ▶) T min = 0.827, T max = 0.907

3753 measured reflections

2525 independent reflections

2123 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.035

wR(F 2) = 0.101

S = 1.06

2525 reflections

169 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.23 e Å−3

Δρmin = −0.25 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/S1600536808033503/zl2153sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808033503/zl2153Isup2.hkl

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

C12H11ClO4S	Z = 2
Mr = 286.72	F(000) = 296
Triclinic, P1	Dx = 1.459 Mg m−3
Hall symbol: -P_1	Melting point = 415–416 K
a = 7.8910 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.9416 (6) Å	Cell parameters from 2313 reflections
c = 10.4048 (7) Å	θ = 2.8–28.2°
α = 73.774 (1)°	µ = 0.46 mm−1
β = 78.743 (1)°	T = 298 K
γ = 68.559 (1)°	Block, colourless
V = 652.55 (7) Å3	0.40 × 0.40 × 0.20 mm

Bruker SMART CCD diffractometer	2525 independent reflections
Radiation source: fine-focus sealed tube	2123 reflections with I > 2σ(I)
graphite	Rint = 0.012
Detector resolution: 10.0 pixels mm-1	θmax = 26.0°, θmin = 2.5°
φ and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1999)	k = −11→7
Tmin = 0.827, Tmax = 0.907	l = −12→12
3753 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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0497P)2 + 0.2053P] where P = (Fo2 + 2Fc2)/3
2525 reflections	(Δ/σ)max < 0.001
169 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.25 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
Cl	−0.22541 (8)	0.20560 (7)	0.87139 (8)	0.0834 (2)
S	0.23616 (7)	0.63233 (7)	0.54121 (5)	0.05176 (17)
O1	0.33659 (17)	0.45642 (16)	0.92043 (12)	0.0468 (3)
O2	0.5278 (2)	0.89402 (19)	0.72451 (19)	0.0728 (5)
O3	0.2521 (2)	0.9006 (2)	0.69823 (19)	0.0748 (5)
O4	0.2462 (2)	0.4995 (2)	0.47609 (15)	0.0688 (4)
C1	0.2400 (2)	0.5423 (2)	0.71481 (17)	0.0429 (4)
C2	0.1418 (2)	0.4347 (2)	0.79676 (17)	0.0424 (4)
C3	0.0067 (3)	0.3789 (2)	0.7780 (2)	0.0489 (4)
H3	−0.040 (3)	0.409 (3)	0.694 (2)	0.053 (6)*
C4	−0.0519 (3)	0.2747 (2)	0.8878 (2)	0.0555 (5)
C5	0.0180 (3)	0.2229 (3)	1.0116 (2)	0.0596 (5)
H5	−0.0254	0.1511	1.0818	0.072*
C6	0.1517 (3)	0.2778 (2)	1.0307 (2)	0.0556 (5)
H6	0.2007	0.2447	1.1124	0.067*
C7	0.2087 (2)	0.3845 (2)	0.92181 (19)	0.0450 (4)
C8	0.3537 (2)	0.5507 (2)	0.79220 (18)	0.0433 (4)
C9	0.4870 (3)	0.6396 (2)	0.7667 (2)	0.0494 (4)
H9A	0.5801	0.6024	0.6959	0.059*
H9B	0.5470	0.6105	0.8475	0.059*
C10	0.4045 (3)	0.8245 (3)	0.72678 (19)	0.0489 (4)
C11	0.4682 (5)	1.0733 (3)	0.6855 (4)	0.1092 (12)
H11A	0.4158	1.1104	0.6016	0.164*
H11B	0.5713	1.1098	0.6754	0.164*
H11C	0.3782	1.1180	0.7537	0.164*
C12	0.0024 (3)	0.7661 (3)	0.5437 (2)	0.0661 (6)
H12A	−0.0223	0.8297	0.4543	0.099*
H12B	−0.0183	0.8390	0.6018	0.099*
H12C	−0.0772	0.7011	0.5764	0.099*

	U11	U22	U33	U12	U13	U23
Cl	0.0594 (4)	0.0550 (3)	0.1360 (6)	−0.0274 (3)	−0.0214 (4)	−0.0029 (4)
S	0.0541 (3)	0.0652 (3)	0.0390 (3)	−0.0251 (2)	−0.0121 (2)	−0.0044 (2)
O1	0.0496 (7)	0.0499 (7)	0.0406 (7)	−0.0133 (6)	−0.0141 (5)	−0.0075 (5)
O2	0.0579 (9)	0.0575 (9)	0.1130 (14)	−0.0244 (7)	−0.0186 (9)	−0.0208 (9)
O3	0.0557 (9)	0.0564 (9)	0.1072 (13)	−0.0179 (7)	−0.0286 (9)	0.0023 (9)
O4	0.0751 (10)	0.0872 (11)	0.0505 (8)	−0.0219 (9)	−0.0140 (7)	−0.0269 (8)
C1	0.0460 (9)	0.0439 (10)	0.0394 (9)	−0.0139 (8)	−0.0101 (7)	−0.0081 (7)
C2	0.0436 (9)	0.0383 (9)	0.0431 (9)	−0.0087 (7)	−0.0086 (7)	−0.0096 (7)
C3	0.0465 (10)	0.0432 (10)	0.0584 (12)	−0.0125 (8)	−0.0119 (9)	−0.0123 (9)
C4	0.0449 (10)	0.0376 (10)	0.0800 (14)	−0.0101 (8)	−0.0095 (10)	−0.0100 (9)
C5	0.0537 (12)	0.0419 (10)	0.0671 (13)	−0.0109 (9)	0.0000 (10)	0.0018 (9)
C6	0.0564 (12)	0.0489 (11)	0.0489 (11)	−0.0091 (9)	−0.0087 (9)	−0.0009 (9)
C7	0.0437 (9)	0.0416 (10)	0.0455 (10)	−0.0078 (8)	−0.0086 (7)	−0.0093 (8)
C8	0.0428 (9)	0.0448 (10)	0.0417 (9)	−0.0107 (8)	−0.0107 (7)	−0.0093 (7)
C9	0.0449 (10)	0.0534 (11)	0.0534 (11)	−0.0163 (8)	−0.0143 (8)	−0.0115 (9)
C10	0.0472 (10)	0.0557 (11)	0.0468 (10)	−0.0193 (9)	−0.0064 (8)	−0.0124 (8)
C11	0.095 (2)	0.0580 (16)	0.186 (4)	−0.0338 (16)	−0.030 (2)	−0.0244 (19)
C12	0.0659 (13)	0.0603 (13)	0.0673 (14)	−0.0152 (11)	−0.0275 (11)	−0.0009 (11)

Cl—C4	1.748 (2)	C4—C5	1.391 (3)
S—O4	1.4950 (17)	C5—C6	1.381 (3)
S—C1	1.7613 (18)	C5—H5	0.9300
S—C12	1.794 (2)	C6—C7	1.380 (3)
O1—C8	1.376 (2)	C6—H6	0.9300
O1—C7	1.377 (2)	C8—C9	1.482 (3)
O2—C10	1.327 (2)	C9—C10	1.504 (3)
O2—C11	1.454 (3)	C9—H9A	0.9700
O3—C10	1.194 (2)	C9—H9B	0.9700
C1—C8	1.350 (2)	C11—H11A	0.9600
C1—C2	1.443 (3)	C11—H11B	0.9600
C2—C7	1.394 (3)	C11—H11C	0.9600
C2—C3	1.396 (3)	C12—H12A	0.9600
C3—C4	1.378 (3)	C12—H12B	0.9600
C3—H3	0.94 (2)	C12—H12C	0.9600
O4—S—C1	105.98 (9)	C6—C7—C2	123.72 (18)
O4—S—C12	106.01 (11)	C1—C8—O1	110.86 (16)
C1—S—C12	98.50 (10)	C1—C8—C9	133.29 (17)
C8—O1—C7	106.35 (13)	O1—C8—C9	115.85 (15)
C10—O2—C11	116.4 (2)	C8—C9—C10	114.36 (15)
C8—C1—C2	107.57 (15)	C8—C9—H9A	108.7
C8—C1—S	124.18 (15)	C10—C9—H9A	108.7
C2—C1—S	127.95 (14)	C8—C9—H9B	108.7
C7—C2—C3	119.64 (17)	C10—C9—H9B	108.7
C7—C2—C1	104.63 (16)	H9A—C9—H9B	107.6
C3—C2—C1	135.72 (17)	O3—C10—O2	123.6 (2)
C4—C3—C2	116.31 (19)	O3—C10—C9	126.28 (19)
C4—C3—H3	121.9 (13)	O2—C10—C9	110.06 (16)
C2—C3—H3	121.8 (13)	O2—C11—H11A	109.5
C3—C4—C5	123.7 (2)	O2—C11—H11B	109.5
C3—C4—Cl	118.25 (17)	H11A—C11—H11B	109.5
C5—C4—Cl	118.09 (16)	O2—C11—H11C	109.5
C6—C5—C4	120.25 (19)	H11A—C11—H11C	109.5
C6—C5—H5	119.9	H11B—C11—H11C	109.5
C4—C5—H5	119.9	S—C12—H12A	109.5
C7—C6—C5	116.40 (19)	S—C12—H12B	109.5
C7—C6—H6	121.8	H12A—C12—H12B	109.5
C5—C6—H6	121.8	S—C12—H12C	109.5
O1—C7—C6	125.70 (17)	H12A—C12—H12C	109.5
O1—C7—C2	110.58 (15)	H12B—C12—H12C	109.5
O4—S—C1—C8	129.68 (17)	C5—C6—C7—C2	−1.4 (3)
C12—S—C1—C8	−120.88 (18)	C3—C2—C7—O1	−178.32 (15)
O4—S—C1—C2	−43.19 (19)	C1—C2—C7—O1	1.0 (2)
C12—S—C1—C2	66.26 (19)	C3—C2—C7—C6	1.4 (3)
C8—C1—C2—C7	−0.4 (2)	C1—C2—C7—C6	−179.31 (18)
S—C1—C2—C7	173.45 (14)	C2—C1—C8—O1	−0.4 (2)
C8—C1—C2—C3	178.8 (2)	S—C1—C8—O1	−174.49 (13)
S—C1—C2—C3	−7.4 (3)	C2—C1—C8—C9	−179.77 (19)
C7—C2—C3—C4	−0.2 (3)	S—C1—C8—C9	6.1 (3)
C1—C2—C3—C4	−179.2 (2)	C7—O1—C8—C1	1.0 (2)
C2—C3—C4—C5	−1.0 (3)	C7—O1—C8—C9	−179.52 (15)
C2—C3—C4—Cl	178.26 (14)	C1—C8—C9—C10	60.7 (3)
C3—C4—C5—C6	1.0 (3)	O1—C8—C9—C10	−118.61 (18)
Cl—C4—C5—C6	−178.22 (16)	C11—O2—C10—O3	0.5 (4)
C4—C5—C6—C7	0.2 (3)	C11—O2—C10—C9	179.1 (2)
C8—O1—C7—C6	179.08 (18)	C8—C9—C10—O3	−10.1 (3)
C8—O1—C7—C2	−1.22 (19)	C8—C9—C10—O2	171.31 (17)
C5—C6—C7—O1	178.32 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11C···Cg1i	0.96	2.92	3.858 (2)	165
C3—H3···O4ii	0.94 (2)	2.41 (2)	3.320 (3)	162.7 (17)
C9—H9B···O1iii	0.97	2.59	3.550 (2)	172
C9—H9A···O4iv	0.97	2.23	3.183 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1/C2/C7/O1/C8 furan ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11C⋯Cg1i	0.96	2.92	3.858 (2)	165
C3—H3⋯O4ii	0.94 (2)	2.41 (2)	3.320 (3)	162.7 (17)
C9—H9B⋯O1iii	0.97	2.59	3.550 (2)	172
C9—H9A⋯O4iv	0.97	2.23	3.183 (3)	169

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