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

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

doi:10.1107/S1600536812049471

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 (C-C) = 0.002 Å
R = 0.043
wR = 0.118
Data-to-parameter ratio = 18.5
Details

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

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

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).

Experimental

Crystal data

C₂₂H₁₄S
M_r = 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 radiation
= 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(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.043
wR(F²) = 0.118
S = 1.03
3855 reflections
208 parameters
H-atom parameters constrained
_max = 0.21 e Å^-3
_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-HA	D-H	HA	DA	D-HA
C5-H5Cg2ⁱ	0.93	2.94	3.8138 (19)	158
C13-H13Cg3ⁱ	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); 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: 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.
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.

organic compounds