5-Bromo-3-(4-fluoro­phenyl­sulfon­yl)-2,7-dimethyl-1-benzofuran

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

doi:10.1107/S1600536812043607

Volume 68
Part 11
Page o3208
November 2012

Received 15 October 2012
Accepted 21 October 2012
Online 27 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean (C-C) = 0.003 Å
R = 0.028
wR = 0.074
Data-to-parameter ratio = 18.3
Details

5-Bromo-3-(4-fluorophenylsulfonyl)-2,7-dimethyl-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, C₁₆H₁₂BrFO₃S, the 4-fluorophenyl ring makes a dihedral angle of 72.35 (5)° with the mean plane [r.m.s. deviation = 0.008 (1) Å] of the benzofuran fragment. In the crystal, molecules are linked into [010] chains via two different inversion-generated pairs of C-HO hydrogen bonds. The crystal structure also exhibits slipped [pi] - [pi] interactions between the benzene rings of neighbouring molecules [centroid-centroid distance = 3.667 (2) Å and slippage = 1.341 (2) Å], and between the benzene and the furan rings of neighbouring molecules [centroid-centroid distance = 3.759 (2) Å and slippage = 0.757 (2) Å].

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2010, 2012).

Experimental

Crystal data

C₁₆H₁₂BrFO₃S
M_r = 383.23
Triclinic, $[P \overline 1]$
a = 8.0789 (1) Å
b = 9.2754 (2) Å
c = 11.3555 (2) Å
= 71.283 (1)°
= 72.645 (1)°
= 70.042 (1)°
V = 740.30 (2) Å³
Z = 2
Mo K radiation
= 2.94 mm^-1
T = 173 K
0.29 × 0.21 × 0.18 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2009) T_min = 0.527, T_max = 0.746
14090 measured reflections
3680 independent reflections
3259 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.028
wR(F²) = 0.074
S = 1.02
3680 reflections
201 parameters
H-atom parameters constrained
_max = 0.36 e Å^-3
_min = -0.47 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

D-HA	D-H	HA	DA	D-HA
C3-H3O2ⁱ	0.95	2.53	3.408 (2)	154
C9-H9AO2ⁱⁱ	0.98	2.50	3.304 (2)	139
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -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: HB6977 ).

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. & Lee, U. (2012). Acta Cryst. E68, o2143.
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2049.
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds