Methyl 2-(5-fluoro-3-methyl­sulfinyl-1-benzofuran-2-yl)acetate

Choi, H.D.; Seo, P.J.; Son, B.W.; Lee, U.

doi:10.1107/S1600536809030451

Volume 65
Part 9
Page o2096
September 2009

Received 21 July 2009
Accepted 31 July 2009
Online 8 August 2009

Key indicators
Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.002 Å
R = 0.032
wR = 0.089
Data-to-parameter ratio = 16.2
Details

Methyl 2-(5-fluoro-3-methylsulfinyl-1-benzofuran-2-yl)acetate

Hong Dae Choi,^a Pil Ja Seo,^a Byeng Wha Son ^b and Uk Lee ^b ^*

^aDepartment of Chemistry, Dongeui University, San 24 Kaya-dong Busanjin-gu, Busan 614-714, Republic of Korea, and ^bDepartment of Chemistry, Pukyong National University, 599-1 Daeyeon 3-dong, Nam-gu, Busan 608-737, Republic of Korea
Correspondence e-mail: uklee@pknu.ac.kr

In the title compound, C₁₂H₁₁FO₄S, the O atom and the methyl group of the methylsulfinyl 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 intermolecular C-HO hydrogen-bond interactions. The crystal structure also exhibits aromatic [pi] - [pi] stacking interactions 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 intermolecular C-H [pi] ring interaction.

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_r = 270.27
Triclinic, $[P \overline 1]$
a = 7.7799 (5) Å
b = 8.5609 (6) Å
c = 10.5592 (7) Å
= 73.834 (1)°
= 80.178 (1)°
= 67.486 (1)°
V = 622.36 (7) Å³
Z = 2
Mo K radiation
= 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 > 2(I)
R_int = 0.014

Refinement

R[F² > 2(F²)] = 0.032
wR(F²) = 0.089
S = 1.08
2667 reflections
165 parameters
H-atom parameters constrained
_max = 0.28 e Å^-3
_min = -0.31 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O4ⁱ	0.93	2.39	3.303 (2)	166
C9-H9AO4ⁱⁱ	0.97	2.22	3.179 (2)	168
C9-H9BO1ⁱⁱⁱ	0.97	2.54	3.489 (2)	166
C12-H12AO3^iv	0.96	2.60	3.478 (2)	152
C11-H11ACg2^v	0.96	2.97	3.93	173
Symmetry codes: (i) -x+1, -y+1, -z; (ii) -x+2, -y+1, -z; (iii) -x+2, -y+1, -z+1; (iv) -x+1, -y+2, -z; (v) x, y+1, z. Cg2 is the centroid of the C2-C7 ring.

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.

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JJ2003 ).

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008a). Acta Cryst. E64, o2139.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2008b). Acta Cryst. E64, o2397.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Howlett, D. R., Perry, A. E., Godfrey, F., Swatton, J. E., Jennings, K. H., Spitzfaden, C., Wadsworth, H., Wood, S. J. & Markwell, R. E. (1999). Biochem. J. 340, 283-289.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Twyman, L. J. & Allsop, D. (1999). Tetrahedron Lett. 40, 9383-9384.

organic compounds