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Volume 69 
Part 1 
Page o36  
January 2013  

Received 19 November 2012
Accepted 3 December 2012
Online 8 December 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.043
wR = 0.118
Data-to-parameter ratio = 18.5
Details
Open access

6-Phenylbenzo[d]naphtho[2,3-b]thiophene

aCAS in Crystallography and Biophysics, University of Madras, Guindy Campus, Chennai-25, India, and bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai-25, India
Correspondence e-mail: shirai2011@gmail.com

In the title compound, C22H14S, the r.m.s. deviation from the mean plane of the four-fused-ring naphthothiophene unit is 0.056 Å. The dihedral angle between the naphthothiophene plane and the pendant phenyl ring is 67.24 (6)°. In the crystal, weak C-H...[pi] and [pi]-[pi] stacking [minimum centroid-centroid separation = 3.7466 (10) Å] interactions are observed, which together lead to (010) sheets.

Related literature

For background to the biological activity of benzothiophene derivatives, see: Isloora et al. (2010[Isloora, A. M., Kalluraya, B. & Sridhar Pai, K. (2010). Eur. J. Med. Chem. 45, 825-830.]).

[Scheme 1]

Experimental

Crystal data
  • C22H14S

  • Mr = 310.40

  • Orthorhombic, P c c n

  • a = 12.6752 (10) Å

  • b = 28.578 (2) Å

  • c = 8.5659 (6) Å

  • V = 3102.8 (4) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.21 mm-1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker APEXII CCD diffractometer

  • 16518 measured reflections

  • 3855 independent reflections

  • 2892 reflections with I > 2[sigma](I)

  • Rint = 0.031

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

  • wR(F2) = 0.118

  • S = 1.03

  • 3855 reflections

  • 208 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.21 e Å-3

  • [Delta][rho]min = -0.24 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1-C6 and C10-C16 rings, respectively.

D-H...A D-H H...A D...A D-H...A
C5-H5...Cg2i 0.93 2.94 3.8138 (19) 158
C13-H13...Cg3i 0.93 2.64 3.5399 (17) 163
Symmetry code: (i) [-x-{\script{1\over 2}}, y, z-{\script{1\over 2}}].

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2 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.]; software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HB6995 ).


Acknowledgements

VS and DV thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, and the UGC SAP for the facilities to the department.

References

Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Isloora, A. M., Kalluraya, B. & Sridhar Pai, K. (2010). Eur. J. Med. Chem. 45, 825-830.  [ISI] [PubMed]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]


Acta Cryst (2013). E69, o36  [ doi:10.1107/S1600536812049471 ]

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