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

The title compound, C(13)H(14)O(4)S, was prepared by oxidation of methyl 2-(5-methyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The O atom and methyl group of the methyl-sulfinyl substituent lie on opposite sides of the plane of the benzofuran system. The crystal structure is stabilized by inter-molecular aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules, with a centroid-centroid separation of 3.841 (3) Å.

Related literature

For the crystal structures of similar ethyl 2-(3-methyl­sulfinyl-1-benzofuran-2-yl)acetate derivatives, see: Choi et al. (2007a ▶,b ▶).

Experimental

Crystal data

C13H14O4S

M = 266.30

Triclinic,

a = 7.9331 (6) Å

b = 8.1097 (6) Å

c = 10.7017 (8) Å

α = 71.601 (1)°

β = 81.107 (1)°

γ = 84.303 (1)°

V = 644.51 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 298 (2) K

0.40 × 0.20 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

3414 measured reflections

2237 independent reflections

1788 reflections with I > 2σ(I)

R int = 0.052

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.123

S = 1.03

2237 reflections

166 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.35 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/S1600536808024689/bh2186sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808024689/bh2186Isup2.hkl

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

C13H14O4S	Z = 2
Mr = 266.30	F000 = 280
Triclinic, P1	Dx = 1.372 Mg m−3
Hall symbol: -P 1	Melting point = 380–381 K
a = 7.9331 (6) Å	Mo Kα radiation λ = 0.71073 Å
b = 8.1097 (6) Å	Cell parameters from 1817 reflections
c = 10.7017 (8) Å	θ = 2.6–27.3º
α = 71.601 (1)º	µ = 0.26 mm−1
β = 81.107 (1)º	T = 298 (2) K
γ = 84.303 (1)º	Block, colorless
V = 644.51 (8) Å3	0.40 × 0.20 × 0.20 mm

Bruker SMART CCD diffractometer	2237 independent reflections
Radiation source: fine-focus sealed tube	1788 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.052
Detector resolution: 10.0 pixels mm-1	θmax = 25.0º
T = 298(2) K	θmin = 2.0º
φ and ω scans	h = −9→9
Absorption correction: none	k = −9→9
3414 measured reflections	l = −9→12

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)] = 0.045	H-atom parameters constrained
wR(F2) = 0.123	w = 1/[σ2(Fo2) + (0.0647P)2 + 0.1924P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
2237 reflections	Δρmax = 0.34 e Å−3
166 parameters	Δρmin = −0.35 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

	x	y	z	Uiso*/Ueq
S	0.22227 (8)	0.36975 (8)	0.45695 (6)	0.0430 (2)
O1	0.16435 (19)	0.5432 (2)	0.07927 (16)	0.0392 (4)
O2	−0.1560 (3)	0.0853 (3)	0.3071 (3)	0.0850 (8)
O3	0.1251 (2)	0.0969 (2)	0.2923 (2)	0.0565 (5)
O4	0.2489 (3)	0.5059 (3)	0.51807 (19)	0.0597 (5)
C1	0.2418 (3)	0.4676 (3)	0.2838 (2)	0.0348 (5)
C2	0.3713 (3)	0.5757 (3)	0.1944 (2)	0.0342 (5)
C3	0.5246 (3)	0.6396 (3)	0.2059 (3)	0.0410 (6)
H3	0.5647	0.6111	0.2877	0.049*
C4	0.6143 (3)	0.7457 (3)	0.0930 (3)	0.0445 (6)
C5	0.5523 (3)	0.7870 (3)	−0.0291 (3)	0.0486 (7)
H5	0.6147	0.8592	−0.1038	0.058*
C6	0.4028 (3)	0.7256 (3)	−0.0442 (3)	0.0460 (6)
H6	0.3628	0.7534	−0.1260	0.055*
C7	0.3168 (3)	0.6199 (3)	0.0709 (2)	0.0366 (5)
C8	0.1227 (3)	0.4533 (3)	0.2103 (2)	0.0352 (5)
C9	−0.0416 (3)	0.3635 (3)	0.2452 (3)	0.0404 (6)
H9A	−0.1049	0.4071	0.1697	0.048*
H9B	−0.1081	0.3975	0.3181	0.048*
C10	−0.0307 (3)	0.1679 (3)	0.2841 (3)	0.0447 (6)
C11	0.1449 (4)	−0.0918 (4)	0.3298 (4)	0.0801 (11)
H11A	0.0761	−0.1409	0.4132	0.120*
H11B	0.2627	−0.1280	0.3382	0.120*
H11C	0.1090	−0.1312	0.2629	0.120*
C12	0.7804 (3)	0.8174 (4)	0.1000 (3)	0.0616 (8)
H12A	0.8119	0.7677	0.1878	0.092*
H12B	0.7661	0.9416	0.0797	0.092*
H12C	0.8685	0.7884	0.0369	0.092*
C13	0.4142 (4)	0.2333 (4)	0.4661 (3)	0.0573 (7)
H13A	0.5112	0.3042	0.4396	0.086*
H13B	0.4176	0.1635	0.4080	0.086*
H13C	0.4167	0.1588	0.5556	0.086*

	U11	U22	U33	U12	U13	U23
S	0.0403 (4)	0.0487 (4)	0.0362 (4)	−0.0034 (3)	−0.0055 (3)	−0.0072 (3)
O1	0.0378 (9)	0.0428 (9)	0.0376 (9)	−0.0039 (7)	−0.0099 (7)	−0.0104 (7)
O2	0.0557 (13)	0.0589 (13)	0.135 (2)	−0.0209 (11)	−0.0173 (13)	−0.0150 (14)
O3	0.0415 (10)	0.0357 (9)	0.0832 (14)	−0.0039 (8)	0.0035 (9)	−0.0100 (9)
O4	0.0708 (13)	0.0711 (13)	0.0456 (11)	0.0066 (10)	−0.0141 (10)	−0.0297 (10)
C1	0.0363 (12)	0.0338 (12)	0.0349 (12)	−0.0017 (9)	−0.0056 (10)	−0.0110 (10)
C2	0.0354 (12)	0.0307 (11)	0.0377 (13)	0.0006 (9)	−0.0047 (10)	−0.0128 (10)
C3	0.0376 (13)	0.0413 (13)	0.0482 (15)	−0.0020 (10)	−0.0082 (11)	−0.0182 (12)
C4	0.0369 (13)	0.0363 (13)	0.0611 (17)	−0.0010 (10)	−0.0039 (12)	−0.0175 (12)
C5	0.0433 (14)	0.0415 (14)	0.0517 (16)	−0.0044 (11)	0.0054 (12)	−0.0060 (12)
C6	0.0492 (15)	0.0442 (14)	0.0397 (14)	−0.0006 (12)	−0.0058 (12)	−0.0065 (11)
C7	0.0337 (12)	0.0341 (12)	0.0435 (14)	0.0006 (9)	−0.0065 (10)	−0.0139 (10)
C8	0.0354 (12)	0.0317 (11)	0.0381 (13)	−0.0004 (9)	−0.0038 (10)	−0.0110 (10)
C9	0.0317 (12)	0.0448 (14)	0.0466 (15)	−0.0027 (10)	−0.0082 (11)	−0.0152 (11)
C10	0.0423 (14)	0.0478 (15)	0.0453 (15)	−0.0094 (11)	−0.0040 (11)	−0.0148 (12)
C11	0.070 (2)	0.0385 (16)	0.115 (3)	−0.0043 (15)	0.006 (2)	−0.0086 (17)
C12	0.0427 (15)	0.0532 (16)	0.088 (2)	−0.0115 (12)	−0.0069 (15)	−0.0182 (16)
C13	0.0571 (17)	0.0524 (16)	0.0596 (18)	0.0078 (13)	−0.0169 (14)	−0.0116 (14)

S—O4	1.495 (2)	C5—H5	0.9300
S—C1	1.759 (2)	C6—C7	1.381 (3)
S—C13	1.788 (3)	C6—H6	0.9300
O1—C8	1.366 (3)	C8—C9	1.495 (3)
O1—C7	1.392 (3)	C9—C10	1.505 (3)
O2—C10	1.204 (3)	C9—H9A	0.9700
O3—C10	1.315 (3)	C9—H9B	0.9700
O3—C11	1.453 (3)	C11—H11A	0.9600
C1—C8	1.354 (3)	C11—H11B	0.9600
C1—C2	1.444 (3)	C11—H11C	0.9600
C2—C7	1.382 (3)	C12—H12A	0.9600
C2—C3	1.405 (3)	C12—H12B	0.9600
C3—C4	1.381 (4)	C12—H12C	0.9600
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.397 (4)	C13—H13B	0.9600
C4—C12	1.513 (3)	C13—H13C	0.9600
C5—C6	1.382 (4)
O4—S—C1	107.63 (11)	O1—C8—C9	116.0 (2)
O4—S—C13	105.85 (13)	C8—C9—C10	117.4 (2)
C1—S—C13	98.82 (13)	C8—C9—H9A	108.0
C8—O1—C7	106.00 (17)	C10—C9—H9A	108.0
C10—O3—C11	117.3 (2)	C8—C9—H9B	108.0
C8—C1—C2	107.3 (2)	C10—C9—H9B	108.0
C8—C1—S	122.09 (18)	H9A—C9—H9B	107.2
C2—C1—S	130.59 (18)	O2—C10—O3	123.6 (2)
C7—C2—C3	119.0 (2)	O2—C10—C9	121.9 (2)
C7—C2—C1	104.91 (19)	O3—C10—C9	114.4 (2)
C3—C2—C1	136.1 (2)	O3—C11—H11A	109.5
C4—C3—C2	118.5 (2)	O3—C11—H11B	109.5
C4—C3—H3	120.8	H11A—C11—H11B	109.5
C2—C3—H3	120.8	O3—C11—H11C	109.5
C3—C4—C5	120.0 (2)	H11A—C11—H11C	109.5
C3—C4—C12	120.5 (3)	H11B—C11—H11C	109.5
C5—C4—C12	119.4 (2)	C4—C12—H12A	109.5
C6—C5—C4	123.0 (2)	C4—C12—H12B	109.5
C6—C5—H5	118.5	H12A—C12—H12B	109.5
C4—C5—H5	118.5	C4—C12—H12C	109.5
C7—C6—C5	115.3 (2)	H12A—C12—H12C	109.5
C7—C6—H6	122.4	H12B—C12—H12C	109.5
C5—C6—H6	122.4	S—C13—H13A	109.5
C6—C7—C2	124.2 (2)	S—C13—H13B	109.5
C6—C7—O1	125.2 (2)	H13A—C13—H13B	109.5
C2—C7—O1	110.58 (19)	S—C13—H13C	109.5
C1—C8—O1	111.21 (19)	H13A—C13—H13C	109.5
C1—C8—C9	132.8 (2)	H13B—C13—H13C	109.5
O4—S—C1—C8	−129.6 (2)	C1—C2—C7—C6	179.0 (2)
C13—S—C1—C8	120.6 (2)	C3—C2—C7—O1	179.36 (19)
O4—S—C1—C2	48.5 (2)	C1—C2—C7—O1	−1.1 (2)
C13—S—C1—C2	−61.4 (2)	C8—O1—C7—C6	−178.8 (2)
C8—C1—C2—C7	0.5 (2)	C8—O1—C7—C2	1.2 (2)
S—C1—C2—C7	−177.78 (18)	C2—C1—C8—O1	0.3 (3)
C8—C1—C2—C3	180.0 (3)	S—C1—C8—O1	178.70 (15)
S—C1—C2—C3	1.7 (4)	C2—C1—C8—C9	−178.3 (2)
C7—C2—C3—C4	0.5 (3)	S—C1—C8—C9	0.1 (4)
C1—C2—C3—C4	−178.9 (2)	C7—O1—C8—C1	−0.9 (2)
C2—C3—C4—C5	−0.1 (4)	C7—O1—C8—C9	177.97 (19)
C2—C3—C4—C12	−179.8 (2)	C1—C8—C9—C10	−72.1 (3)
C3—C4—C5—C6	−0.3 (4)	O1—C8—C9—C10	109.3 (2)
C12—C4—C5—C6	179.4 (2)	C11—O3—C10—O2	0.7 (4)
C4—C5—C6—C7	0.3 (4)	C11—O3—C10—C9	179.8 (3)
C5—C6—C7—C2	0.2 (4)	C8—C9—C10—O2	−176.1 (3)
C5—C6—C7—O1	−179.8 (2)	C8—C9—C10—O3	4.8 (3)
C3—C2—C7—C6	−0.6 (3)