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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 [sigma](C-C) = 0.003 Å
R = 0.028
wR = 0.074
Data-to-parameter ratio = 18.3
Details
Open access

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

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-H...O 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[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2049.], 2012[Choi, H. D., Seo, P. J. & Lee, U. (2012). Acta Cryst. E68, o2143.]).

[Scheme 1]

Experimental

Crystal data
  • C16H12BrFO3S

  • Mr = 383.23

  • Triclinic, [P \overline 1]

  • a = 8.0789 (1) Å

  • b = 9.2754 (2) Å

  • c = 11.3555 (2) Å

  • [alpha] = 71.283 (1)°

  • [beta] = 72.645 (1)°

  • [gamma] = 70.042 (1)°

  • V = 740.30 (2) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.527, Tmax = 0.746

  • 14090 measured reflections

  • 3680 independent reflections

  • 3259 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.028

  • wR(F2) = 0.074

  • S = 1.02

  • 3680 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.36 e Å-3

  • [Delta][rho]min = -0.47 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C3-H3...O2i 0.95 2.53 3.408 (2) 154
C9-H9A...O2ii 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[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2, SADABS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and DIAMOND (Brandenburg, 1998[Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany.]); 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.  [CSD] [CrossRef] [details]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o2049.  [CSD] [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3208  [ doi:10.1107/S1600536812043607 ]

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