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

In the title compound, C(12)H(11)FO(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 [O-S-C-C and C-S-C-C torsion angles = 126.70 (13) and -123.55 (13)°, respectively]. The crystal structure is stabilized by weak non-classical inter-molecular C-H⋯O hydrogen-bond inter-actions. The crystal structure also exhibits aromatic π-π stacking inter-actions between furan/benzene and benzene/benzene rings of adjacent benzofuran ring systems [centroid-centroid distances = 3.8258 (9) and 3.8794 (9) Å] and a weak inter-molecular C-H⋯π ring inter-action.

Related literature

For crystal structures of similar methyl 2-(5-halo-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate derivatives. see: Choi et al. (2008a ▶,b ▶). For the pharmacological properties of benzofuran compounds, see: Howlett et al. (1999 ▶); Twyman & Allsop (1999 ▶).

Experimental

Crystal data

C12H11FO4S

M = 270.27

Triclinic,

a = 7.7799 (5) Å

b = 8.5609 (6) Å

c = 10.5592 (7) Å

α = 73.834 (1)°

β = 80.178 (1)°

γ = 67.486 (1)°

V = 622.36 (7) Å3

Z = 2

Mo Kα radiation

μ = 0.28 mm−1

T = 273 K

0.60 × 0.40 × 0.40 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: none

5368 measured reflections

2667 independent reflections

2389 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.032

wR(F 2) = 0.089

S = 1.08

2667 reflections

165 parameters

H-atom parameters constrained

Δρmax = 0.28 e Å−3

Δρmin = −0.31 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/S1600536809030451/jj2003sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809030451/jj2003Isup2.hkl

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

C12H11FO4S	Z = 2
Mr = 270.27	F(000) = 280
Triclinic, P1	Dx = 1.442 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.7799 (5) Å	Cell parameters from 3896 reflections
b = 8.5609 (6) Å	θ = 2.7–27.5°
c = 10.5592 (7) Å	µ = 0.28 mm−1
α = 73.834 (1)°	T = 273 K
β = 80.178 (1)°	Block, colorless
γ = 67.486 (1)°	0.60 × 0.40 × 0.40 mm
V = 622.36 (7) Å3

Bruker SMART CCD diffractometer	2389 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.014
graphite	θmax = 27.0°, θmin = 2.0°
Detector resolution: 10.0 pixels mm-1	h = −9→9
φ and ω scans	k = −10→10
5368 measured reflections	l = −13→13
2667 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)] = 0.032	Hydrogen site location: difference Fourier map
wR(F2) = 0.089	H-atom parameters constrained
S = 1.08	w = 1/[σ2(Fo2) + (0.0432P)2 + 0.227P] where P = (Fo2 + 2Fc2)/3
2667 reflections	(Δ/σ)max = 0.001
165 parameters	Δρmax = 0.28 e Å−3
0 restraints	Δρmin = −0.31 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.73212 (5)	0.63256 (5)	0.04928 (3)	0.03039 (12)
F	0.30035 (14)	0.21264 (13)	0.37311 (11)	0.0513 (3)
O1	0.84250 (14)	0.43881 (13)	0.42317 (9)	0.0288 (2)
O2	1.04499 (16)	0.88742 (15)	0.21928 (13)	0.0436 (3)
O3	0.75373 (16)	0.90527 (15)	0.20563 (13)	0.0449 (3)
O4	0.75098 (17)	0.49556 (16)	−0.02040 (11)	0.0415 (3)
C1	0.73869 (19)	0.53270 (18)	0.21918 (13)	0.0263 (3)
C2	0.63718 (19)	0.42498 (17)	0.29942 (13)	0.0261 (3)
C3	0.4978 (2)	0.37061 (19)	0.27953 (15)	0.0309 (3)
H3	0.4480	0.4036	0.1981	0.037*
C4	0.4390 (2)	0.26551 (19)	0.38775 (17)	0.0352 (3)
C5	0.5098 (2)	0.2096 (2)	0.51151 (16)	0.0375 (4)
H5	0.4641	0.1377	0.5804	0.045*
C6	0.6489 (2)	0.26217 (19)	0.53113 (15)	0.0342 (3)
H6	0.7000	0.2268	0.6124	0.041*
C7	0.70799 (19)	0.36995 (18)	0.42381 (14)	0.0275 (3)
C8	0.85804 (19)	0.53640 (18)	0.29708 (13)	0.0264 (3)
C9	0.9967 (2)	0.62392 (19)	0.27115 (14)	0.0290 (3)
H9A	1.0886	0.5816	0.2024	0.035*
H9B	1.0611	0.5919	0.3506	0.035*
C10	0.9129 (2)	0.82024 (19)	0.22925 (14)	0.0296 (3)
C11	0.9865 (3)	1.0754 (2)	0.1780 (3)	0.0657 (6)
H11A	0.9333	1.1147	0.0941	0.099*
H11B	1.0924	1.1099	0.1701	0.099*
H11C	0.8950	1.1261	0.2425	0.099*
C12	0.4904 (2)	0.7705 (2)	0.04906 (17)	0.0386 (4)
H12A	0.4625	0.8393	−0.0388	0.058*
H12B	0.4656	0.8458	0.1077	0.058*
H12C	0.4139	0.7000	0.0782	0.058*

	U11	U22	U33	U12	U13	U23
S	0.0313 (2)	0.0392 (2)	0.02016 (18)	−0.01352 (15)	−0.00616 (13)	−0.00224 (14)
F	0.0428 (6)	0.0440 (6)	0.0702 (7)	−0.0247 (5)	−0.0127 (5)	0.0003 (5)
O1	0.0340 (5)	0.0313 (5)	0.0211 (5)	−0.0111 (4)	−0.0076 (4)	−0.0034 (4)
O2	0.0324 (6)	0.0323 (6)	0.0661 (8)	−0.0123 (5)	−0.0036 (5)	−0.0104 (5)
O3	0.0323 (6)	0.0356 (6)	0.0588 (8)	−0.0086 (5)	−0.0120 (5)	0.0019 (5)
O4	0.0454 (7)	0.0528 (7)	0.0277 (6)	−0.0129 (5)	−0.0069 (5)	−0.0154 (5)
C1	0.0278 (7)	0.0284 (7)	0.0209 (6)	−0.0074 (5)	−0.0053 (5)	−0.0046 (5)
C2	0.0270 (7)	0.0249 (6)	0.0237 (6)	−0.0050 (5)	−0.0036 (5)	−0.0065 (5)
C3	0.0294 (7)	0.0285 (7)	0.0334 (7)	−0.0070 (6)	−0.0071 (6)	−0.0069 (6)
C4	0.0295 (7)	0.0278 (7)	0.0477 (9)	−0.0100 (6)	−0.0051 (6)	−0.0065 (6)
C5	0.0389 (8)	0.0275 (7)	0.0382 (8)	−0.0103 (6)	0.0018 (6)	0.0000 (6)
C6	0.0403 (8)	0.0299 (7)	0.0261 (7)	−0.0082 (6)	−0.0043 (6)	−0.0017 (6)
C7	0.0283 (7)	0.0267 (7)	0.0261 (7)	−0.0065 (5)	−0.0045 (5)	−0.0070 (5)
C8	0.0276 (7)	0.0264 (7)	0.0217 (6)	−0.0055 (5)	−0.0048 (5)	−0.0041 (5)
C9	0.0265 (7)	0.0315 (7)	0.0285 (7)	−0.0078 (6)	−0.0080 (5)	−0.0061 (5)
C10	0.0302 (7)	0.0338 (7)	0.0238 (7)	−0.0112 (6)	−0.0019 (5)	−0.0055 (5)
C11	0.0528 (12)	0.0333 (9)	0.1083 (19)	−0.0182 (9)	−0.0025 (12)	−0.0103 (10)
C12	0.0349 (8)	0.0362 (8)	0.0382 (8)	−0.0074 (6)	−0.0134 (6)	0.0001 (6)

S—O4	1.500 (2)	C4—C5	1.391 (2)
S—C1	1.760 (1)	C5—C6	1.385 (2)
S—C12	1.797 (2)	C5—H5	0.9300
F—C4	1.365 (2)	C6—C7	1.383 (2)
O1—C8	1.374 (2)	C6—H6	0.9300
O1—C7	1.382 (2)	C8—C9	1.484 (2)
O2—C10	1.335 (2)	C9—C10	1.514 (2)
O2—C11	1.450 (2)	C9—H9A	0.9700
O3—C10	1.200 (2)	C9—H9B	0.9700
C1—C8	1.355 (2)	C11—H11A	0.9600
C1—C2	1.444 (2)	C11—H11B	0.9600
C2—C7	1.398 (2)	C11—H11C	0.9600
C2—C3	1.398 (2)	C12—H12A	0.9600
C3—C4	1.374 (2)	C12—H12B	0.9600
C3—H3	0.9300	C12—H12C	0.9600
O4—S—C1	106.58 (7)	C6—C7—C2	123.8 (1)
O4—S—C12	106.22 (8)	C1—C8—O1	111.2 (1)
C1—S—C12	98.29 (7)	C1—C8—C9	132.4 (1)
C8—O1—C7	106.3 (1)	O1—C8—C9	116.5 (1)
C10—O2—C11	116.0 (1)	C8—C9—C10	114.0 (1)
C8—C1—C2	107.3 (1)	C8—C9—H9A	108.8
C8—C1—S	123.2 (1)	C10—C9—H9A	108.8
C2—C1—S	129.4 (1)	C8—C9—H9B	108.8
C7—C2—C3	119.5 (1)	C10—C9—H9B	108.8
C7—C2—C1	104.8 (1)	H9A—C9—H9B	107.7
C3—C2—C1	135.8 (1)	O3—C10—O2	124.1 (1)
C4—C3—C2	115.9 (1)	O3—C10—C9	126.4 (1)
C4—C3—H3	122.1	O2—C10—C9	109.5 (1)
C2—C3—H3	122.1	O2—C11—H11A	109.5
F—C4—C3	117.7 (1)	O2—C11—H11B	109.5
F—C4—C5	117.5 (1)	H11A—C11—H11B	109.5
C3—C4—C5	124.8 (2)	O2—C11—H11C	109.5
C6—C5—C4	119.4 (1)	H11A—C11—H11C	109.5
C6—C5—H5	120.3	H11B—C11—H11C	109.5
C4—C5—H5	120.3	S—C12—H12A	109.5
C7—C6—C5	116.6 (1)	S—C12—H12B	109.5
C7—C6—H6	121.7	H12A—C12—H12B	109.5
C5—C6—H6	121.7	S—C12—H12C	109.5
O1—C7—C6	125.7 (1)	H12A—C12—H12C	109.5
O1—C7—C2	110.5 (1)	H12B—C12—H12C	109.5
O4—S—C1—C8	126.70 (13)	C5—C6—C7—C2	−0.8 (2)
C12—S—C1—C8	−123.55 (13)	C3—C2—C7—O1	−179.47 (12)
O4—S—C1—C2	−48.22 (14)	C1—C2—C7—O1	0.62 (15)
C12—S—C1—C2	61.53 (14)	C3—C2—C7—C6	0.3 (2)
C8—C1—C2—C7	−0.35 (15)	C1—C2—C7—C6	−179.62 (13)
S—C1—C2—C7	175.19 (11)	C2—C1—C8—O1	−0.04 (16)
C8—C1—C2—C3	179.77 (15)	S—C1—C8—O1	−175.92 (9)
S—C1—C2—C3	−4.7 (2)	C2—C1—C8—C9	−179.96 (14)
C7—C2—C3—C4	0.6 (2)	S—C1—C8—C9	4.2 (2)
C1—C2—C3—C4	−179.54 (15)	C7—O1—C8—C1	0.42 (15)
C2—C3—C4—F	178.65 (12)	C7—O1—C8—C9	−179.65 (12)
C2—C3—C4—C5	−1.0 (2)	C1—C8—C9—C10	61.1 (2)
F—C4—C5—C6	−179.15 (14)	O1—C8—C9—C10	−118.82 (13)
C3—C4—C5—C6	0.5 (2)	C11—O2—C10—O3	0.5 (2)
C4—C5—C6—C7	0.4 (2)	C11—O2—C10—C9	179.20 (16)
C8—O1—C7—C6	179.59 (14)	C8—C9—C10—O3	−6.6 (2)
C8—O1—C7—C2	−0.65 (14)	C8—C9—C10—O2	174.75 (12)
C5—C6—C7—O1	178.93 (13)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3···O4i	0.93	2.39	3.303 (2)	166
C9—H9A···O4ii	0.97	2.22	3.179 (2)	168
C9—H9B···O1iii	0.97	2.54	3.489 (2)	166
C12—H12A···O3iv	0.96	2.60	3.478 (2)	152
C11—H11A···Cg2v	0.96	2.97	3.93	173

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3⋯O4i	0.93	2.39	3.303 (2)	166
C9—H9A⋯O4ii	0.97	2.22	3.179 (2)	168
C9—H9B⋯O1iii	0.97	2.54	3.489 (2)	166
C12—H12A⋯O3iv	0.96	2.60	3.478 (2)	152
C11—H11A⋯Cg2v	0.96	2.97	3.93	173

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg2 is the centroid of the C2–C7 ring.