3-Ethyl­sulfinyl-2-(3-fluoro­phen­yl)-5,6-methyl­enedi­oxy-1-benzofuran

Choi, H.D.; Seo, P.J.; Lee, U.

doi:10.1107/S1600536812044832

Volume 68
Part 12
Page o3339
December 2012

Received 25 October 2012
Accepted 30 October 2012
Online 14 November 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.002 Å
R = 0.038
wR = 0.101
Data-to-parameter ratio = 17.2
Details

3-Ethylsulfinyl-2-(3-fluorophenyl)-5,6-methylenedioxy-1-benzofuran

Hong Dae Choi,^a Pil Ja Seo ^a 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, C₁₇H₁₃FO₄S, the 3-fluorophenyl ring makes a dihedral angle of 6.14 (5)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked by weak C-HF, C-HO and C-H [pi] interactions, forming a three--dimensional network. The crystal structure also exhibits slipped [pi] - [pi] interactions between the 3-fluorophenyl rings of neighbouring molecules [centroid-centroid distance = 3.769 (2) Å and slippage = 1.684 (2) Å].

Related literature

For background information on and the crystal structures of related benzofuran compounds, see: Choi et al. (2010); Seo et al. (2011).

Experimental

Crystal data

C₁₇H₁₃FO₄S
M_r = 332.33
Monoclinic, P 2₁ /c
a = 8.8516 (2) Å
b = 21.8221 (4) Å
c = 7.7228 (2) Å
= 102.949 (1)°
V = 1453.80 (6) Å³
Z = 4
Mo K radiation
= 0.25 mm^-1
T = 173 K
0.39 × 0.29 × 0.26 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.908, T_max = 0.937
14376 measured reflections
3600 independent reflections
3131 reflections with I > 2(I)
R_int = 0.025

Refinement

R[F² > 2(F²)] = 0.038
wR(F²) = 0.101
S = 1.02
3600 reflections
209 parameters
H-atom parameters constrained
_max = 0.45 e Å^-3
_min = -0.35 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2-C7 benzene ring.

D-HA	D-H	HA	DA	D-HA
C9-H9AO4ⁱ	0.99	2.45	3.314 (2)	145
C9-H9BO2ⁱⁱ	0.99	2.59	3.519 (3)	156
C16-H16AO4ⁱⁱⁱ	0.99	2.29	3.2689 (19)	169
C6-H6F1^iv	0.95	2.37	3.2532 (18)	154
C17-H17BCg1^v	0.98	2.74	3.642 (3)	153
Symmetry codes: (i) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) x+1, y, z+1; (v) x, y, z-1.

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); 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: MW2094 ).

Acknowledgements

This work was supported by the Blue-Bio Industry Regional Innovation Center (RIC08-06-07) at Dongeui University as an RIC program under the Ministry of Knowledge Economy and Busan City.

References

Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.
Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1296.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o3504.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds