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Volume 69 
Part 7 
Page o1148  
July 2013  

Received 17 June 2013
Accepted 19 June 2013
Online 22 June 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.004 Å
R = 0.043
wR = 0.117
Data-to-parameter ratio = 18.6
Details
Open access

7-Bromo-2-(4-methylphenyl)-1-(methylsulfinyl)naphtho[2,1-b]furan

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, C20H15BrO2S, the dihedral angle between the mean plane [r.m.s. deviation = 0.030 (2) Å] of the naphthofuran ring system and the 4-methylphenyl ring is 38.49 (9)°. In the crystal, molecules are linked by C-H...[pi] and C-Br...[pi] [3.871 (2) Å] interactions into stacks along the b-axis direction. These stacks are further linked by weak C-H...O hydrogen bonds, forming a three-dimensional network.

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, o1956.], 2010[Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1012.]).

[Scheme 1]

Experimental

Crystal data
  • C20H15BrO2S

  • Mr = 399.29

  • Monoclinic, P 21 /c

  • a = 6.2198 (11) Å

  • b = 23.234 (4) Å

  • c = 11.344 (2) Å

  • [beta] = 94.733 (12)°

  • V = 1633.7 (5) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 2.65 mm-1

  • T = 173 K

  • 0.27 × 0.19 × 0.11 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 = 0.472, Tmax = 0.746

  • 16182 measured reflections

  • 4083 independent reflections

  • 3135 reflections with I > 2[sigma](I)

  • Rint = 0.070

Refinement
  • R[F2 > 2[sigma](F2)] = 0.043

  • wR(F2) = 0.117

  • S = 1.04

  • 4083 reflections

  • 219 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 1.16 e Å-3

  • [Delta][rho]min = -0.63 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2/C3/C8/C9/C10/C11 benzene ring.

D-H...A D-H H...A D...A D-H...A
C19-H19A...O2i 0.98 2.52 3.476 (4) 166
C14-H14...Cg1ii 0.95 2.68 3.342 (4) 127
Symmetry codes: (i) [x+1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) x+1, y, z.

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, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) 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: HG5324 ).


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, o1956.  [CSD] [CrossRef] [IUCr Journals]
Choi, H. D., Seo, P. J., Son, B. W. & Lee, U. (2010). Acta Cryst. E66, o1012.  [CSD] [CrossRef] [IUCr Journals]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [Web of Science] [CrossRef] [ChemPort] [IUCr Journals]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [ChemPort] [IUCr Journals]


Acta Cryst (2013). E69, o1148  [ doi:10.1107/S1600536813016978 ]

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