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

The title compound, C(15)H(18)O(4)S, was prepared by the oxidation of isopropyl 2-(5-methyl-3-methyl-sulfanyl-1-benzofuran-2-yl)acetate with 3-chloro-peroxy-benzoic acid. The crystal structure is stabilized by inter-molecular π-π inter-actions between the benzene rings; the centroid-centroid distance between the adjacent benzene rings (symmetry code: ) is 3.713 (2) Å. In addition, C-H⋯π and weak inter-molecular C-H⋯O inter-actions are present in the structure.

Related literature

For the crystal structures of similar 2-(5-methyl-3-methyl­sulfinyl-1-benzofuran-2-yl)acetic acid derivatives, see: Choi et al. (2007 ▶, 2008 ▶).

Experimental

Crystal data

C15H18O4S

M = 294.35

Triclinic,

a = 8.1829 (5) Å

b = 9.7027 (6) Å

c = 10.6545 (7) Å

α = 73.057 (1)°

β = 77.463 (1)°

γ = 66.421 (1)°

V = 736.76 (8) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 298 (2) K

0.40 × 0.30 × 0.30 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

5802 measured reflections

2838 independent reflections

2479 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.105

S = 1.07

2838 reflections

185 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.24 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/S1600536808031796/fb2111sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808031796/fb2111Isup2.hkl

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

C15H18O4S	Z = 2
Mr = 294.35	F(000) = 312
Triclinic, P1	Dx = 1.327 Mg m−3
Hall symbol: -P_1	Melting point = 403–404 K
a = 8.1829 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.7027 (6) Å	Cell parameters from 4030 reflections
c = 10.6545 (7) Å	θ = 2.4–28.2°
α = 73.057 (1)°	µ = 0.23 mm−1
β = 77.463 (1)°	T = 298 K
γ = 66.421 (1)°	Block, colourless
V = 736.76 (8) Å3	0.40 × 0.30 × 0.30 mm

Bruker SMART CCD diffractometer	2479 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.035
graphite	θmax = 26.0°, θmin = 2.7°
Detector resolution: 10.0 pixels mm-1	h = −10→10
φ and ω scans	k = −11→11
5802 measured reflections	l = −13→13
2838 independent 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) = 0.105	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0509P)2 + 0.2101P] where P = (Fo2 + 2Fc2)/3
2838 reflections	(Δ/σ)max < 0.001
185 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.24 e Å−3
68 constraints

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
S	0.74200 (6)	0.64759 (5)	0.04151 (4)	0.04706 (16)
O1	0.84827 (15)	0.47478 (12)	0.40980 (11)	0.0378 (3)
O2	0.7528 (2)	0.53592 (18)	−0.03283 (14)	0.0705 (4)
O3	0.73496 (17)	0.88857 (15)	0.23749 (16)	0.0603 (4)
O4	1.00780 (15)	0.88109 (12)	0.25158 (12)	0.0422 (3)
C1	0.7543 (2)	0.55223 (18)	0.20899 (15)	0.0356 (3)
C2	0.6619 (2)	0.45172 (16)	0.29204 (15)	0.0336 (3)
C3	0.5364 (2)	0.39518 (18)	0.27713 (16)	0.0380 (4)
H3	0.4913	0.4233	0.1967	0.046*
C4	0.4806 (2)	0.29641 (19)	0.38454 (17)	0.0405 (4)
C5	0.5499 (2)	0.25528 (19)	0.50517 (17)	0.0424 (4)
H5	0.5109	0.1888	0.5761	0.051*
C6	0.6736 (2)	0.30967 (18)	0.52246 (16)	0.0401 (4)
H6	0.7189	0.2818	0.6027	0.048*
C7	0.7260 (2)	0.40767 (17)	0.41396 (15)	0.0343 (3)
C8	0.8622 (2)	0.56095 (18)	0.28352 (15)	0.0361 (3)
C9	0.9868 (2)	0.64659 (18)	0.25585 (18)	0.0405 (4)
H9A	1.0607	0.6321	0.1728	0.049*
H9B	1.0657	0.6029	0.3247	0.049*
C10	0.8915 (2)	0.81825 (18)	0.24831 (16)	0.0384 (4)
C11	0.3469 (3)	0.2312 (3)	0.3719 (2)	0.0598 (5)
H11A	0.2959	0.2846	0.2902	0.090*
H11B	0.2533	0.2443	0.4443	0.090*
H11C	0.4066	0.1232	0.3731	0.090*
C12	0.5114 (3)	0.7722 (3)	0.0561 (2)	0.0717 (6)
H12A	0.4814	0.8392	−0.0284	0.108*
H12B	0.4926	0.8332	0.1182	0.108*
H12C	0.4367	0.7112	0.0865	0.108*
C13	0.9392 (2)	1.04906 (18)	0.24297 (18)	0.0426 (4)
H13	0.8239	1.0791	0.2982	0.051*
C14	0.9158 (3)	1.1356 (2)	0.1023 (2)	0.0603 (5)
H14A	0.8323	1.1104	0.0707	0.090*
H14B	1.0294	1.1071	0.0488	0.090*
H14C	0.8708	1.2446	0.0974	0.090*
C15	1.0762 (3)	1.0762 (2)	0.2963 (3)	0.0692 (6)
H15A	1.1907	1.0407	0.2453	0.104*
H15B	1.0850	1.0206	0.3868	0.104*
H15C	1.0407	1.1846	0.2910	0.104*

	U11	U22	U33	U12	U13	U23
S	0.0572 (3)	0.0469 (3)	0.0365 (2)	−0.0241 (2)	−0.00906 (19)	0.00182 (17)
O1	0.0416 (6)	0.0381 (6)	0.0392 (6)	−0.0204 (5)	−0.0113 (5)	−0.0035 (5)
O2	0.0994 (12)	0.0694 (9)	0.0444 (8)	−0.0262 (9)	−0.0159 (8)	−0.0158 (7)
O3	0.0408 (7)	0.0449 (7)	0.0966 (11)	−0.0190 (6)	−0.0103 (7)	−0.0113 (7)
O4	0.0420 (6)	0.0328 (6)	0.0568 (7)	−0.0177 (5)	−0.0114 (5)	−0.0075 (5)
C1	0.0406 (8)	0.0324 (7)	0.0355 (8)	−0.0163 (7)	−0.0064 (6)	−0.0040 (6)
C2	0.0373 (8)	0.0292 (7)	0.0352 (8)	−0.0128 (6)	−0.0055 (6)	−0.0067 (6)
C3	0.0411 (9)	0.0370 (8)	0.0415 (8)	−0.0167 (7)	−0.0096 (7)	−0.0098 (7)
C4	0.0394 (9)	0.0362 (8)	0.0512 (10)	−0.0175 (7)	−0.0047 (7)	−0.0124 (7)
C5	0.0458 (9)	0.0356 (8)	0.0454 (9)	−0.0205 (7)	−0.0016 (7)	−0.0031 (7)
C6	0.0449 (9)	0.0377 (8)	0.0375 (8)	−0.0165 (7)	−0.0095 (7)	−0.0024 (6)
C7	0.0357 (8)	0.0304 (7)	0.0394 (8)	−0.0140 (6)	−0.0076 (6)	−0.0063 (6)
C8	0.0395 (8)	0.0312 (7)	0.0386 (8)	−0.0159 (6)	−0.0057 (6)	−0.0040 (6)
C9	0.0396 (9)	0.0376 (8)	0.0490 (9)	−0.0200 (7)	−0.0070 (7)	−0.0068 (7)
C10	0.0394 (9)	0.0387 (8)	0.0397 (8)	−0.0206 (7)	−0.0038 (7)	−0.0038 (6)
C11	0.0605 (12)	0.0615 (12)	0.0731 (13)	−0.0393 (10)	−0.0128 (10)	−0.0095 (10)
C12	0.0665 (14)	0.0616 (13)	0.0692 (14)	−0.0084 (11)	−0.0246 (11)	0.0023 (11)
C13	0.0444 (9)	0.0327 (8)	0.0540 (10)	−0.0160 (7)	−0.0051 (8)	−0.0119 (7)
C14	0.0797 (15)	0.0395 (10)	0.0607 (12)	−0.0235 (10)	−0.0124 (10)	−0.0039 (8)
C15	0.0745 (15)	0.0483 (11)	0.1006 (18)	−0.0231 (11)	−0.0311 (13)	−0.0232 (11)

S—O2	1.4839 (15)	C8—C9	1.490 (2)
S—C1	1.7583 (16)	C9—C10	1.516 (2)
S—C12	1.790 (2)	C9—H9A	0.9700
O1—C8	1.3698 (18)	C9—H9B	0.9700
O1—C7	1.3830 (18)	C11—H11A	0.9600
O3—C10	1.199 (2)	C11—H11B	0.9600
O4—C10	1.3305 (19)	C11—H11C	0.9600
O4—C13	1.4774 (19)	C12—H12A	0.9600
C1—C8	1.349 (2)	C12—H12B	0.9600
C1—C2	1.450 (2)	C12—H12C	0.9600
C2—C7	1.392 (2)	C13—C15	1.500 (3)
C2—C3	1.397 (2)	C13—C14	1.500 (3)
C3—C4	1.386 (2)	C13—H13	0.9800
C3—H3	0.9300	C14—H14A	0.9600
C4—C5	1.403 (2)	C14—H14B	0.9600
C4—C11	1.511 (2)	C14—H14C	0.9600
C5—C6	1.379 (2)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.376 (2)	C15—H15C	0.9600
C6—H6	0.9300
O2—S—C1	108.11 (8)	H9A—C9—H9B	107.7
O2—S—C12	106.21 (11)	O3—C10—O4	124.63 (15)
C1—S—C12	97.74 (9)	O3—C10—C9	125.20 (14)
C8—O1—C7	106.03 (11)	O4—C10—C9	110.14 (13)
C10—O4—C13	117.80 (13)	C4—C11—H11A	109.5
C8—C1—C2	107.31 (13)	C4—C11—H11B	109.5
C8—C1—S	123.03 (12)	H11A—C11—H11B	109.5
C2—C1—S	129.65 (12)	C4—C11—H11C	109.5
C7—C2—C3	119.08 (14)	H11A—C11—H11C	109.5
C7—C2—C1	104.42 (13)	H11B—C11—H11C	109.5
C3—C2—C1	136.50 (15)	S—C12—H12A	109.5
C4—C3—C2	118.66 (15)	S—C12—H12B	109.5
C4—C3—H3	120.7	H12A—C12—H12B	109.5
C2—C3—H3	120.7	S—C12—H12C	109.5
C3—C4—C5	119.95 (15)	H12A—C12—H12C	109.5
C3—C4—C11	120.26 (16)	H12B—C12—H12C	109.5
C5—C4—C11	119.79 (16)	O4—C13—C15	105.45 (14)
C6—C5—C4	122.50 (15)	O4—C13—C14	109.85 (14)
C6—C5—H5	118.7	C15—C13—C14	112.29 (17)
C4—C5—H5	118.7	O4—C13—H13	109.7
C7—C6—C5	116.08 (15)	C15—C13—H13	109.7
C7—C6—H6	122.0	C14—C13—H13	109.7
C5—C6—H6	122.0	C13—C14—H14A	109.5
C6—C7—O1	125.47 (14)	C13—C14—H14B	109.5
C6—C7—C2	123.73 (14)	H14A—C14—H14B	109.5
O1—C7—C2	110.80 (13)	C13—C14—H14C	109.5
C1—C8—O1	111.44 (13)	H14A—C14—H14C	109.5
C1—C8—C9	132.89 (15)	H14B—C14—H14C	109.5
O1—C8—C9	115.66 (13)	C13—C15—H15A	109.5
C8—C9—C10	113.54 (14)	C13—C15—H15B	109.5
C8—C9—H9A	108.9	H15A—C15—H15B	109.5
C10—C9—H9A	108.9	C13—C15—H15C	109.5
C8—C9—H9B	108.9	H15A—C15—H15C	109.5
C10—C9—H9B	108.9	H15B—C15—H15C	109.5
O2—S—C1—C8	133.07 (16)	C3—C2—C7—C6	0.4 (2)
C12—S—C1—C8	−117.00 (17)	C1—C2—C7—C6	−179.35 (15)
O2—S—C1—C2	−45.61 (17)	C3—C2—C7—O1	−179.98 (13)
C12—S—C1—C2	64.32 (17)	C1—C2—C7—O1	0.30 (17)
C8—C1—C2—C7	0.00 (18)	C2—C1—C8—O1	−0.30 (19)
S—C1—C2—C7	178.83 (13)	S—C1—C8—O1	−179.23 (11)
C8—C1—C2—C3	−179.65 (18)	C2—C1—C8—C9	−178.84 (17)
S—C1—C2—C3	−0.8 (3)	S—C1—C8—C9	2.2 (3)
C7—C2—C3—C4	−0.3 (2)	C7—O1—C8—C1	0.48 (18)
C1—C2—C3—C4	179.36 (17)	C7—O1—C8—C9	179.29 (13)
C2—C3—C4—C5	0.1 (2)	C1—C8—C9—C10	74.3 (2)
C2—C3—C4—C11	−179.20 (16)	O1—C8—C9—C10	−104.20 (16)
C3—C4—C5—C6	0.0 (3)	C13—O4—C10—O3	0.8 (2)
C11—C4—C5—C6	179.31 (17)	C13—O4—C10—C9	179.02 (13)
C4—C5—C6—C7	0.1 (3)	C8—C9—C10—O3	−14.9 (2)
C5—C6—C7—O1	−179.86 (15)	C8—C9—C10—O4	166.85 (14)
C5—C6—C7—C2	−0.3 (2)	C10—O4—C13—C15	160.41 (17)
C8—O1—C7—C6	179.16 (15)	C10—O4—C13—C14	−78.39 (19)
C8—O1—C7—C2	−0.48 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O2i	0.97	2.38	3.249 (2)	149
C13—H13···Cg1ii	0.98	2.91	3.656 (2)	134
C15—H15C···Cg2ii	0.96	2.96	3.837 (2)	152

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C1/C2/C7/C8/O1 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C9—H9A⋯O2i	0.97	2.38	3.249 (2)	149
C13—H13⋯Cg1ii	0.98	2.91	3.656 (2)	134
C15—H15C⋯Cg2ii	0.96	2.96	3.837 (2)	152

Symmetry codes: (i) ; (ii) .