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Volume 68 
Part 12 
Pages o3408-o3409  
December 2012  

Received 18 October 2012
Accepted 16 November 2012
Online 24 November 2012

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.002 Å
R = 0.046
wR = 0.140
Data-to-parameter ratio = 18.7
Details
Open access

6-(4-Methoxyphenyl)naphtho[2,3-b][1]benzothiophene

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

The asymmetric unit of the title compound, C23H16OS, contains two independent molecules with opposite orientations of the methoxy groups bonded to the benzene rings. The napthobenzothiophene group in the two molecules is separated by an average distance of 3.912 Å. In both molecules, the napthobenzothiophene unit is almost planar, with r.m.s deviations of 0.0522 and 0.0143 Å. The methoxyphenyl ring makes dihedral angles of 67.0 (6)° and 70.4 (6)° with respect to the napthobenzothiophene ring system in the two molecules. The crystal packing features C-H...S, [pi]-[pi] [centroid-centroid distances = 3.666 (10) and 3.658 (10) Å] and C-H...[pi] interactions, forming a sheet running along the b-axis direction.

Related literature

For the biological activity of thiophene derivatives, see: Bonini et al. (2005[Bonini, C., Chiummiento, L., Bonis, M. D., Funicello, M., Lupattelli, P., Suanno, G., Berti, F. & Campaner, P. (2005). Tetrahedron. 61, 6580-6583.]); Brault et al. (2005[Brault, L., Migianu, E., Neguesque, A., Battaglia, E., Bagrel, D. & Kirsch, G. (2005). Eur. J. Med. Chem. 40, 757-760.]); Isloora et al. (2010[Isloora, A. M., Kalluraya, B. & Sridhar Pai, K. (2010). Eur. J. Med. Chem. 45, 825-830.]); Xia et al. (2010[Xia, G.-M., Ji, M.-W., Lu, P., Sun, G.-X. & Xu, W.-F. (2010). Acta Cryst. E66, o148.]). For a related structure, see: Gunasekaran et al. (2010[Gunasekaran, B., Dhayalan, V., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2010). Acta Cryst. E66, o1449.]).

[Scheme 1]

Experimental

Crystal data
  • C23H16OS

  • Mr = 340.42

  • Triclinic, [P \overline 1]

  • a = 6.2019 (3) Å

  • b = 11.2124 (6) Å

  • c = 24.4724 (13) Å

  • [alpha] = 95.759 (3)°

  • [beta] = 91.762 (3)°

  • [gamma] = 95.617 (3)°

  • V = 1683.63 (15) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.20 mm-1

  • T = 293 K

  • 0.20 × 0.20 × 0.20 mm

Data collection
  • Bruker SMART APEXII area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]) Tmin = 0.981, Tmax = 0.985

  • 30236 measured reflections

  • 8440 independent reflections

  • 6029 reflections with I > 2[sigma](I)

  • Rint = 0.041

Refinement
  • R[F2 > 2[sigma](F2)] = 0.046

  • wR(F2) = 0.140

  • S = 1.03

  • 8440 reflections

  • 451 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.37 e Å-3

  • [Delta][rho]min = -0.28 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg2, Cg5 and Cg15 are the centroids of the C2-C7, C18-C23 and C9'-C14' rings, respectively.

D-H...A D-H H...A D...A D-H...A
C6'-H6'...S1'i 0.93 2.87 3.7591 (17) 160
C3'-H3'...Cg15ii 0.93 2.93 3.704 (2) 141
C7-H7...Cg5iii 0.93 2.89 3.672 (2) 143
C11-H11...Cg2iv 0.93 2.91 3.789 (2) 159
Symmetry codes: (i) x-1, y, z; (ii) -x, -y, -z+2; (iii) -x+1, -y, -z+1; (iv) -x+2, -y+1, -z+1.

Data collection: APEX2 (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); cell refinement: SAINT (Bruker, 2008[Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.]); 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: PV2598 ).


Acknowledgements

The authors thank the TBI X-ray facility, CAS in Crystallography and Biophysics, University of Madras, India, for the data collection and VS and DV also thank the UGC SAP for financial support.

References

Bonini, C., Chiummiento, L., Bonis, M. D., Funicello, M., Lupattelli, P., Suanno, G., Berti, F. & Campaner, P. (2005). Tetrahedron. 61, 6580-6583.  [CrossRef] [ChemPort]
Brault, L., Migianu, E., Neguesque, A., Battaglia, E., Bagrel, D. & Kirsch, G. (2005). Eur. J. Med. Chem. 40, 757-760.  [ISI] [CrossRef] [PubMed] [ChemPort]
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Gunasekaran, B., Dhayalan, V., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2010). Acta Cryst. E66, o1449.  [CSD] [CrossRef] [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]
Xia, G.-M., Ji, M.-W., Lu, P., Sun, G.-X. & Xu, W.-F. (2010). Acta Cryst. E66, o148.  [CSD] [CrossRef] [details]


Acta Cryst (2012). E68, o3408-o3409   [ doi:10.1107/S1600536812047137 ]

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