3-[(4-Oxo-4H-thio­chromen-3-yl)meth­yl]-4H-thio­chromen-4-one

Somasundaram, M.; Athavan, S.; Balasubramanian, K.K.; Saiganesh, R.; Kabilan, S.

doi:10.1107/S1600536813001906

Volume 69
Part 3
Page o358
March 2013

Received 30 October 2012
Accepted 18 January 2013
Online 9 February 2013

Key indicators
Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.002 Å
R = 0.033
wR = 0.118
Data-to-parameter ratio = 15.0
Details

3-[(4-Oxo-4H-thiochromen-3-yl)methyl]-4H-thiochromen-4-one

M. Somasundaram,^a S. Athavan,^a K. K. Balasubramanian,^b R. Saiganesh ^b and S. Kabilan ^a ^*

^aDepartment of Chemistry, Annamalai University, Annamalai Nagar, Chidambaram, India, and ^bShasun Reaearch Centre, 27 Vandaloor Kelambakkam Road, Keezhakottaiyur, Meelakottaiyur Post, Chennai, India
Correspondence e-mail: soma78@gmail.com

The title molecule, C₁₉H₁₂S₂O₂, lies on a twofold rotation axis. The thiochromonone unit is essentially planar, with a maximum deviation of 0.0491 (14) Å. The dihedral angle between the thiochromenone ring systems is 64.48 (4)°. In the crystal, there are weak [pi] - [pi] stacking interactions, with a centroid-centroid distance of 3.7147 (9) Å.

Related literature

For backgound to bis-chromonones, see: Santhosh & Balasubramanian (1991); Panja et al. (2009). For related structures, see: Ambartsumyan et al. (2012); Nyburg et al. (1986); Li et al. (2010).

Experimental

Crystal data

C₁₉H₁₂O₂S₂
M_r = 336.41
Monoclinic, C 2/c
a = 11.9480 (5) Å
b = 11.8649 (5) Å
c = 11.1416 (5) Å
= 108.918 (2)°
V = 1494.14 (11) Å³
Z = 4
Mo K radiation
= 0.36 mm^-1
T = 298 K
0.38 × 0.28 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2007) T_min = 0.875, T_max = 0.931
5040 measured reflections
1631 independent reflections
1410 reflections with I > 2(I)
R_int = 0.019

Refinement

R[F² > 2(F²)] = 0.033
wR(F²) = 0.118
S = 0.88
1631 reflections
109 parameters
H atoms treated by a mixture of independent and constrained refinement
_max = 0.27 e Å^-3
_min = -0.22 e Å^-3

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Jmol (Hanson, 2010); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: LH5551 ).

Acknowledgements

The authors thank the University Grants Commission, New Delhi, India, for financial support in the form of a Major Research Project. In addition, they express their thanks to Dr Jai Anand Garg for his valuable support in the preparation of this structure report.

References

Ambartsumyan, A. A., Vasiléva, T. T., Chakhovskaya, O. V., Mysova, N. E., Tuskaev, V. A., Khrustalev, V. N. & Kochetkov, K. A. (2012). Russ. J. Org. Chem. 48, 451-455.
Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hanson, R. M. (2010). J. Appl. Cryst. 43, 1250-1260.
Li, Y., Xiao, T., Liu, D. & Yu, G. (2010). Acta Cryst. E66, o694.
Nyburg, S. C., Prasad, L., Leong, T. S. & Still, I. W. J. (1986). Acta Cryst. C42, 816-821.
Panja, S. K., Maiti, S., Drew, M. G. B. & Bandyopadhyay, Ch. (2009). Tetrahedron, 65, 1276-1280.
Santhosh, K. C. & Balasubramanian, K. K. (1991). Tetrahedron Lett. 32, 7727-7730.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Spek, A. L. (2009). Acta Cryst. D65, 148-155.

organic compounds