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Volume 69 
Part 5 
Page o763  
May 2013  

Received 6 March 2013
Accepted 7 April 2013
Online 20 April 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.004 Å
R = 0.059
wR = 0.180
Data-to-parameter ratio = 17.6
Details
Open access

rac-7-Methyl-3-[(7-methyl-4-oxochroman-3-yl)methyl]-4H-chromen-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

In the racemic title compound, C21H18O4, the chromone ring is essentially planar [maximum deviation from the least-squares plane = 0.026 (3) Å], with a dihedral angle of 78.18 (12)° between the benzene rings of the chromanone and chromenone moieties. In the crystal, there are weak [pi]-[pi] stacking interactions [minimum ring centroid separation = 3.9286 (17) Å].

Related literature

For backgound to bis-chromanones, see: Dean & Murray (1975[Dean, F. M. & Murray, S. (1975). J. Chem. Soc. Perkin Trans. 1, pp. 1706-1711.]); 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
  • C21H18O4

  • Mr = 334.35

  • Monoclinic, P 21 /n

  • a = 10.664 (2) Å

  • b = 6.6428 (13) Å

  • c = 23.754 (5) Å

  • [beta] = 91.11 (3)°

  • V = 1682.4 (6) Å3

  • Z = 4

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.44 × 0.22 × 0.22 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 = 0.961, Tmax = 0.980

  • 11780 measured reflections

  • 4032 independent reflections

  • 1982 reflections with I > 2[sigma](I)

  • Rint = 0.029

Refinement
  • R[F2 > 2[sigma](F2)] = 0.059

  • wR(F2) = 0.180

  • S = 1.02

  • 4032 reflections

  • 229 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.43 e Å-3

  • [Delta][rho]min = -0.30 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: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: ZS2250 ).


Acknowledgements

The authors are thankful to the University Grants Commission, New Delhi, India, for financial support in the form of a Major Research Project. In addition, they express thanks to Dr Srinivasulu and Dr Jai Anand Garg for their 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.
Dean, F. M. & Murray, S. (1975). J. Chem. Soc. Perkin Trans. 1, pp. 1706-1711.  [CrossRef]
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] [ChemPort] [details]


Acta Cryst (2013). E69, o763  [ doi:10.1107/S1600536813009422 ]

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