Ethyl 2-(3-ethyl-sulfinyl-5-methyl-1-benzo-furan-2-yl)acetate.

The title compound, C(15)H(18)O(4)S, was prepared by the oxidation of ethyl 2-(3-ethyl-sulfanyl-5-methyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The crystal structure is stabilized by aromatic π-π inter-actions between the benzene rings of neighbouring mol-ecules [centroid-centroid distance = 3.655 (3) Å] and by three inter-molecular C-H⋯O non-classical hydrogen bonds.

Related literature

For the crystal structures of similar alkyl 2-(5-methyl-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate derivatives, see: Choi et al. (2008a ▶,b ▶).

Experimental

Crystal data

C15H18O4S

M = 294.36

Monoclinic,

a = 7.9651 (5) Å

b = 17.397 (1) Å

c = 10.6902 (7) Å

β = 102.431 (1)°

V = 1446.60 (16) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 293 K

0.40 × 0.35 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

12350 measured reflections

3148 independent reflections

2949 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.114

S = 1.27

3148 reflections

184 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.33 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/S1600536809008460/rk2133sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008460/rk2133Isup2.hkl

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

C15H18O4S	F(000) = 624
Mr = 294.36	Dx = 1.352 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7772 reflections
a = 7.9651 (5) Å	θ = 2.3–28.2°
b = 17.397 (1) Å	µ = 0.23 mm−1
c = 10.6902 (7) Å	T = 293 K
β = 102.431 (1)°	Block, colourless
V = 1446.60 (16) Å3	0.40 × 0.35 × 0.30 mm
Z = 4

Bruker SMART CCD diffractometer	2949 reflections with I > 2σ(I)
Radiation source: Fine-focus sealed tube	Rint = 0.037
graphite	θmax = 27.0°, θmin = 2.3°
Detector resolution: 10.0 pixels mm-1	h = −10→10
φ and ω scans	k = −22→22
12350 measured reflections	l = −13→13
3148 independent reflections

Refinement on F2	Primary atom site location: Direct
Least-squares matrix: Full	Secondary atom site location: Difmap
R[F2 > 2σ(F2)] = 0.052	Hydrogen site location: Difmap
wR(F2) = 0.114	H-atom parameters constrained
S = 1.27	w = 1/[σ2(Fo2) + (0.0313P)2 + 1.0305P] where P = (Fo2 + 2Fc2)/3
3148 reflections	(Δ/σ)max < 0.001
184 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.33 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.28613 (7)	0.56219 (3)	0.92537 (5)	0.02864 (15)
O1	0.34278 (18)	0.48031 (8)	0.59291 (13)	0.0264 (3)
O2	0.69183 (19)	0.68219 (9)	0.71529 (15)	0.0346 (4)
O3	0.4106 (2)	0.68573 (9)	0.71809 (18)	0.0420 (4)
O4	0.2363 (2)	0.50522 (10)	1.01572 (15)	0.0407 (4)
C1	0.2712 (3)	0.51603 (11)	0.77684 (19)	0.0251 (4)
C2	0.1341 (3)	0.46731 (11)	0.70835 (19)	0.0243 (4)
C3	−0.0237 (3)	0.44088 (11)	0.72840 (19)	0.0267 (4)
H3	−0.0606	0.4539	0.8025	0.032*
C4	−0.1244 (3)	0.39479 (11)	0.6356 (2)	0.0284 (4)
C5	−0.0667 (3)	0.37595 (12)	0.5239 (2)	0.0303 (5)
H5	−0.1357	0.3453	0.4623	0.036*
C6	0.0892 (3)	0.40148 (12)	0.5024 (2)	0.0293 (4)
H6	0.1266	0.3886	0.4285	0.035*
C7	0.1861 (2)	0.44711 (11)	0.59661 (19)	0.0245 (4)
C8	0.3903 (3)	0.52184 (11)	0.70459 (19)	0.0253 (4)
C9	0.5568 (3)	0.56329 (12)	0.7224 (2)	0.0284 (4)
H9A	0.6154	0.5470	0.6563	0.034*
H9B	0.6280	0.5487	0.8045	0.034*
C10	0.5396 (3)	0.64999 (12)	0.71761 (19)	0.0278 (4)
C11	0.6973 (3)	0.76628 (13)	0.7098 (2)	0.0398 (6)
H11A	0.8137	0.7838	0.7442	0.048*
H11B	0.6235	0.7877	0.7623	0.048*
C12	0.6400 (4)	0.79423 (16)	0.5758 (3)	0.0537 (7)
H12A	0.7059	0.7693	0.5222	0.080*
H12B	0.6567	0.8488	0.5734	0.080*
H12C	0.5203	0.7826	0.5454	0.080*
C13	−0.2954 (3)	0.36439 (14)	0.6536 (2)	0.0385 (5)
H13A	−0.2898	0.3094	0.6617	0.058*
H13B	−0.3839	0.3782	0.5810	0.058*
H13C	−0.3213	0.3863	0.7298	0.058*
C14	0.1037 (3)	0.62590 (13)	0.8750 (2)	0.0352 (5)
H14A	0.1247	0.6597	0.8078	0.042*
H14B	0.0016	0.5958	0.8406	0.042*
C15	0.0745 (4)	0.67308 (15)	0.9860 (2)	0.0464 (6)
H15A	0.0334	0.6405	1.0455	0.070*
H15B	−0.0093	0.7122	0.9555	0.070*
H15C	0.1806	0.6967	1.0281	0.070*

	U11	U22	U33	U12	U13	U23
S	0.0286 (3)	0.0315 (3)	0.0249 (3)	0.0021 (2)	0.00368 (19)	−0.0026 (2)
O1	0.0259 (7)	0.0274 (7)	0.0267 (7)	0.0001 (6)	0.0075 (6)	−0.0001 (6)
O2	0.0277 (8)	0.0286 (8)	0.0471 (9)	−0.0027 (6)	0.0068 (7)	0.0024 (7)
O3	0.0333 (9)	0.0303 (8)	0.0651 (12)	0.0018 (7)	0.0169 (8)	−0.0043 (8)
O4	0.0523 (10)	0.0428 (9)	0.0289 (8)	0.0086 (8)	0.0132 (7)	0.0077 (7)
C1	0.0267 (10)	0.0232 (10)	0.0251 (10)	0.0009 (8)	0.0047 (8)	0.0020 (8)
C2	0.0265 (10)	0.0199 (9)	0.0255 (10)	0.0029 (8)	0.0038 (8)	0.0044 (7)
C3	0.0286 (10)	0.0245 (10)	0.0281 (10)	0.0022 (8)	0.0084 (8)	0.0053 (8)
C4	0.0262 (10)	0.0218 (10)	0.0358 (11)	0.0017 (8)	0.0037 (8)	0.0066 (8)
C5	0.0316 (11)	0.0225 (10)	0.0331 (11)	0.0012 (8)	−0.0012 (8)	0.0003 (8)
C6	0.0347 (11)	0.0249 (10)	0.0277 (11)	0.0034 (9)	0.0056 (8)	−0.0003 (8)
C7	0.0230 (10)	0.0211 (9)	0.0294 (10)	0.0025 (8)	0.0055 (8)	0.0034 (8)
C8	0.0249 (10)	0.0228 (9)	0.0273 (10)	0.0033 (8)	0.0035 (8)	0.0030 (8)
C9	0.0244 (10)	0.0270 (10)	0.0340 (11)	0.0008 (8)	0.0072 (8)	0.0018 (8)
C10	0.0270 (10)	0.0297 (11)	0.0266 (10)	−0.0019 (8)	0.0055 (8)	−0.0016 (8)
C11	0.0368 (13)	0.0275 (11)	0.0533 (15)	−0.0086 (10)	0.0056 (11)	−0.0040 (10)
C12	0.0513 (16)	0.0412 (14)	0.0632 (18)	−0.0083 (12)	0.0006 (13)	0.0123 (13)
C13	0.0309 (12)	0.0327 (12)	0.0513 (14)	−0.0050 (9)	0.0078 (10)	0.0045 (10)
C14	0.0357 (12)	0.0345 (12)	0.0353 (12)	0.0064 (10)	0.0077 (9)	0.0016 (9)
C15	0.0588 (17)	0.0400 (14)	0.0425 (14)	0.0167 (12)	0.0150 (12)	0.0009 (11)

S—O4	1.4960 (17)	C8—C9	1.485 (3)
S—C1	1.760 (2)	C9—C10	1.514 (3)
S—C14	1.815 (2)	C9—H9A	0.9700
O1—C8	1.377 (2)	C9—H9B	0.9700
O1—C7	1.384 (2)	C11—C12	1.488 (4)
O2—C10	1.341 (2)	C11—H11A	0.9700
O2—C11	1.465 (3)	C11—H11B	0.9700
O3—C10	1.202 (3)	C12—H12A	0.9600
C1—C8	1.350 (3)	C12—H12B	0.9600
C1—C2	1.450 (3)	C12—H12C	0.9600
C2—C7	1.391 (3)	C13—H13A	0.9600
C2—C3	1.398 (3)	C13—H13B	0.9600
C3—C4	1.388 (3)	C13—H13C	0.9600
C3—H3	0.9300	C14—C15	1.502 (3)
C4—C5	1.408 (3)	C14—H14A	0.9700
C4—C13	1.512 (3)	C14—H14B	0.9700
C5—C6	1.383 (3)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.380 (3)	C15—H15C	0.9600
C6—H6	0.9300
O4—S—C1	107.72 (10)	H9A—C9—H9B	107.6
O4—S—C14	106.81 (10)	O3—C10—O2	124.1 (2)
C1—S—C14	96.70 (10)	O3—C10—C9	125.91 (19)
C8—O1—C7	105.99 (15)	O2—C10—C9	109.95 (17)
C10—O2—C11	116.92 (17)	O2—C11—C12	111.1 (2)
C8—C1—C2	107.49 (18)	O2—C11—H11A	109.4
C8—C1—S	124.25 (16)	C12—C11—H11A	109.4
C2—C1—S	128.26 (15)	O2—C11—H11B	109.4
C7—C2—C3	119.49 (19)	C12—C11—H11B	109.4
C7—C2—C1	104.49 (17)	H11A—C11—H11B	108.0
C3—C2—C1	136.00 (19)	C11—C12—H12A	109.5
C4—C3—C2	118.71 (19)	C11—C12—H12B	109.5
C4—C3—H3	120.6	H12A—C12—H12B	109.5
C2—C3—H3	120.6	C11—C12—H12C	109.5
C3—C4—C5	119.81 (19)	H12A—C12—H12C	109.5
C3—C4—C13	120.5 (2)	H12B—C12—H12C	109.5
C5—C4—C13	119.7 (2)	C4—C13—H13A	109.5
C6—C5—C4	122.3 (2)	C4—C13—H13B	109.5
C6—C5—H5	118.8	H13A—C13—H13B	109.5
C4—C5—H5	118.8	C4—C13—H13C	109.5
C7—C6—C5	116.40 (19)	H13A—C13—H13C	109.5
C7—C6—H6	121.8	H13B—C13—H13C	109.5
C5—C6—H6	121.8	C15—C14—S	110.46 (17)
C6—C7—O1	125.83 (18)	C15—C14—H14A	109.6
C6—C7—C2	123.28 (19)	S—C14—H14A	109.6
O1—C7—C2	110.86 (17)	C15—C14—H14B	109.6
C1—C8—O1	111.17 (17)	S—C14—H14B	109.6
C1—C8—C9	132.92 (19)	H14A—C14—H14B	108.1
O1—C8—C9	115.91 (17)	C14—C15—H15A	109.5
C8—C9—C10	114.04 (17)	C14—C15—H15B	109.5
C8—C9—H9A	108.7	H15A—C15—H15B	109.5
C10—C9—H9A	108.7	C14—C15—H15C	109.5
C8—C9—H9B	108.7	H15A—C15—H15C	109.5
C10—C9—H9B	108.7	H15B—C15—H15C	109.5
O4—S—C1—C8	−135.83 (18)	C3—C2—C7—C6	−0.1 (3)
C14—S—C1—C8	114.09 (19)	C1—C2—C7—C6	−178.86 (18)
O4—S—C1—C2	45.4 (2)	C3—C2—C7—O1	178.44 (17)
C14—S—C1—C2	−64.7 (2)	C1—C2—C7—O1	−0.3 (2)
C8—C1—C2—C7	0.3 (2)	C2—C1—C8—O1	−0.2 (2)
S—C1—C2—C7	179.27 (15)	S—C1—C8—O1	−179.20 (13)
C8—C1—C2—C3	−178.1 (2)	C2—C1—C8—C9	179.7 (2)
S—C1—C2—C3	0.8 (3)	S—C1—C8—C9	0.7 (3)
C7—C2—C3—C4	0.1 (3)	C7—O1—C8—C1	0.0 (2)
C1—C2—C3—C4	178.4 (2)	C7—O1—C8—C9	−179.93 (16)
C2—C3—C4—C5	−0.3 (3)	C1—C8—C9—C10	−67.8 (3)
C2—C3—C4—C13	179.55 (18)	O1—C8—C9—C10	112.1 (2)
C3—C4—C5—C6	0.3 (3)	C11—O2—C10—O3	−1.6 (3)
C13—C4—C5—C6	−179.5 (2)	C11—O2—C10—C9	179.64 (18)
C4—C5—C6—C7	−0.3 (3)	C8—C9—C10—O3	10.4 (3)
C5—C6—C7—O1	−178.14 (18)	C8—C9—C10—O2	−170.85 (17)
C5—C6—C7—C2	0.2 (3)	C10—O2—C11—C12	−83.1 (3)
C8—O1—C7—C6	178.71 (19)	O4—S—C14—C15	66.5 (2)
C8—O1—C7—C2	0.2 (2)	C1—S—C14—C15	177.38 (18)

D—H···A	D—H	H···A	D···A	D—H···A
C5—H5···O3i	0.93	2.64	3.507 (3)	155
C6—H6···O2ii	0.93	2.63	3.511 (3)	158
C9—H9B···O4iii	0.97	2.20	3.161 (3)	169

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C5—H5⋯O3i	0.93	2.64	3.507 (3)	155
C6—H6⋯O2ii	0.93	2.63	3.511 (3)	158
C9—H9B⋯O4iii	0.97	2.20	3.161 (3)	169

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