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Volume 68 
Part 11 
Page o3242  
November 2012  

Received 18 October 2012
Accepted 24 October 2012
Online 31 October 2012

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
R = 0.030
wR = 0.079
Data-to-parameter ratio = 17.2
Details
Open access

5-Bromo-3-(4-fluorophenylsulfinyl)-2-phenyl-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, C20H12BrFO2S, the dihedral angles between the mean plane [r.m.s. deviation = 0.006 (2) Å] of the benzofuran fragment and the pendant 4-fluorophenyl and phenyl rings are 84.98 (5) and 40.98 (6)°, respectively. In the crystal, molecules are linked by C-H...O and C-H...[pi] interactions.

Related literature

For background information and the crystal structures of related compounds, see: Choi et al. (2009[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2009). Acta Cryst. E65, o2609.]); Seo et al. (2011[Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.]).

[Scheme 1]

Experimental

Crystal data
  • C20H12BrFO2S

  • Mr = 415.27

  • Triclinic, [P \overline 1]

  • a = 9.2288 (2) Å

  • b = 9.4790 (2) Å

  • c = 10.4939 (2) Å

  • [alpha] = 67.396 (1)°

  • [beta] = 89.933 (1)°

  • [gamma] = 82.373 (1)°

  • V = 838.74 (3) Å3

  • Z = 2

  • Mo K[alpha] radiation

  • [mu] = 2.60 mm-1

  • T = 173 K

  • 0.39 × 0.33 × 0.22 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 = 0.557, Tmax = 0.746

  • 15136 measured reflections

  • 3888 independent reflections

  • 3417 reflections with I > 2[sigma](I)

  • Rint = 0.045

Refinement
  • R[F2 > 2[sigma](F2)] = 0.030

  • wR(F2) = 0.079

  • S = 1.05

  • 3888 reflections

  • 226 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.65 e Å-3

  • [Delta][rho]min = -0.74 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C9-C14 phenyl ring.

D-H...A D-H H...A D...A D-H...A
C10-H10...O2i 0.95 2.41 3.341 (3) 167
C19-H19...O1ii 0.95 2.50 3.447 (2) 175
C16-H16...Cgiii 0.95 2.99 3.832 (2) 148
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) x, y, z-1; (iii) -x, -y+1, -z+2.

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: BV2213 ).


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. (2009). Acta Cryst. E65, o2609.  [CrossRef] [details]
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  [CrossRef] [details]
Seo, P. J., Choi, H. D., Son, B. W. & Lee, U. (2011). Acta Cryst. E67, o2346.  [CSD] [CrossRef] [details]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2012). E68, o3242  [ doi:10.1107/S1600536812044054 ]

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