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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 [sigma](C-C) = 0.002 Å
R = 0.033
wR = 0.118
Data-to-parameter ratio = 15.0
Details
Open access

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

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[Santhosh, K. C. & Balasubramanian, K. K. (1991). Tetrahedron Lett. 32, 7727-7730.]); Panja et al. (2009[Panja, S. K., Maiti, S., Drew, M. G. B. & Bandyopadhyay, Ch. (2009). Tetrahedron, 65, 1276-1280.]). For related structures, see: Ambartsumyan et al. (2012[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.]); Nyburg et al. (1986[Nyburg, S. C., Prasad, L., Leong, T. S. & Still, I. W. J. (1986). Acta Cryst. C42, 816-821.]); Li et al. (2010[Li, Y., Xiao, T., Liu, D. & Yu, G. (2010). Acta Cryst. E66, o694.]).

[Scheme 1]

Experimental

Crystal data
  • C19H12O2S2

  • Mr = 336.41

  • Monoclinic, C 2/c

  • a = 11.9480 (5) Å

  • b = 11.8649 (5) Å

  • c = 11.1416 (5) Å

  • [beta] = 108.918 (2)°

  • V = 1494.14 (11) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 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[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.875, Tmax = 0.931

  • 5040 measured reflections

  • 1631 independent reflections

  • 1410 reflections with I > 2[sigma](I)

  • Rint = 0.019

Refinement
  • R[F2 > 2[sigma](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

  • [Delta][rho]max = 0.27 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Data collection: SMART (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). SMART, SAINT and SADABS. 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: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and Jmol (Hanson, 2010[Hanson, R. M. (2010). J. Appl. Cryst. 43, 1250-1260.]); software used to prepare material for publication: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]).


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.  [ISI] [CrossRef] [ChemPort]
Bruker (2007). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Hanson, R. M. (2010). J. Appl. Cryst. 43, 1250-1260.  [ISI] [CrossRef] [ChemPort] [details]
Li, Y., Xiao, T., Liu, D. & Yu, G. (2010). Acta Cryst. E66, o694.  [CSD] [CrossRef] [details]
Nyburg, S. C., Prasad, L., Leong, T. S. & Still, I. W. J. (1986). Acta Cryst. C42, 816-821.  [CrossRef] [details]
Panja, S. K., Maiti, S., Drew, M. G. B. & Bandyopadhyay, Ch. (2009). Tetrahedron, 65, 1276-1280.  [ISI] [CSD] [CrossRef] [ChemPort]
Santhosh, K. C. & Balasubramanian, K. K. (1991). Tetrahedron Lett. 32, 7727-7730.  [CrossRef] [ChemPort] [ISI]
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, o358  [ doi:10.1107/S1600536813001906 ]

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