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

Silambarasan, V.; Srinivasan, T.; Sivasakthikumaran, R.; Mohanakrishnan, A.K.; Velmurugan, D.

doi:10.1107/S1600536812047137

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 (C-C) = 0.002 Å
R = 0.046
wR = 0.140
Data-to-parameter ratio = 18.7
Details

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

V. Silambarasan,^a T. Srinivasan,^a R. Sivasakthikumaran,^b A. K. Mohanakrishnan ^b and D. Velmurugan ^a ^*

^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-HS, [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); Brault et al. (2005); Isloora et al. (2010); Xia et al. (2010). For a related structure, see: Gunasekaran et al. (2010).

Experimental

Crystal data

C₂₃H₁₆OS
M_r = 340.42
Triclinic, $[P \overline 1]$
a = 6.2019 (3) Å
b = 11.2124 (6) Å
c = 24.4724 (13) Å
= 95.759 (3)°
= 91.762 (3)°
= 95.617 (3)°
V = 1683.63 (15) Å³
Z = 4
Mo K radiation
= 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) T_min = 0.981, T_max = 0.985
30236 measured reflections
8440 independent reflections
6029 reflections with I > 2(I)
R_int = 0.041

Refinement

R[F² > 2(F²)] = 0.046
wR(F²) = 0.140
S = 1.03
8440 reflections
451 parameters
H-atom parameters constrained
_max = 0.37 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C6'-H6'S1'ⁱ	0.93	2.87	3.7591 (17)	160
C3'-H3'Cg15ⁱⁱ	0.93	2.93	3.704 (2)	141
C7-H7Cg5ⁱⁱⁱ	0.93	2.89	3.672 (2)	143
C11-H11Cg2^iv	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); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009).

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.
Brault, L., Migianu, E., Neguesque, A., Battaglia, E., Bagrel, D. & Kirsch, G. (2005). Eur. J. Med. Chem. 40, 757-760.
Bruker (2008). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, U. S. A.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Gunasekaran, B., Dhayalan, V., Mohanakrishnan, A. K., Chakkaravarthi, G. & Manivannan, V. (2010). Acta Cryst. E66, o1449.
Isloora, A. M., Kalluraya, B. & Sridhar Pai, K. (2010). Eur. J. Med. Chem. 45, 825-830.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.
Xia, G.-M., Ji, M.-W., Lu, P., Sun, G.-X. & Xu, W.-F. (2010). Acta Cryst. E66, o148.

organic compounds