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Volume 69 
Part 2 
Page o241  
February 2013  

Received 25 November 2012
Accepted 10 January 2013
Online 16 January 2013

Key indicators
Single-crystal X-ray study
T = 295 K
Mean [sigma](C-C) = 0.003 Å
R = 0.045
wR = 0.142
Data-to-parameter ratio = 13.9
Details
Open access

3-(3,4-Dimethoxybenzyl)chroman-4-one

aChemistry Research Centre (affiliated to Kuvempu University), SSMRV Degree College, 4th T Block, Jayanagar, Bangalore 560 041, India,bDepartment of Chemistry, KMC International Center, Manipal University, Manipal 576 104, India,cDepartment of Pharmaceutical Chemistry, Manipal College of Pharmaceutical Sciences, Manipal University, Manipal 576 104, India,dDepartment of Chemistry, Jnana Sahyadri, Kuvempu University, Shankargatta 577 451, India, and eDepartment of Physics, Bhavan's Sheth R. A. College of Science, Khanpur, Ahmedabad, Gujarat 380 001, India
Correspondence e-mail: girija.shivakumar@rediffmail.com

In the title compound, C18H18O4, the six-membered chroman-4-one ring adopts an envelope conformation with the C atom bonded to the bridging CH2 atom as the flap. The dihedral angle between the mean plane of the fused pyranone ring and the dimethoxy-substituted benzene ring is 89.72 (2)°. In the crystal, adjacent molecules are linked via C-H...[pi] interactions.

Related literature

For the biological activity and pharmaceutical properties of chromenes(benzopyrans) and a similar structure, see: Jasinski et al. (2010[Jasinski, J. P., Pek, A. E., Narayana, B., Yathirajan, H. S. & Nayak, P. S. (2010). Acta Cryst. E66, o2546-o2547.]). For bond-length data see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ring conformations, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.])

[Scheme 1]

Experimental

Crystal data
  • C18H18O4

  • Mr = 298.33

  • Monoclinic, C 2/c

  • a = 30.414 (4) Å

  • b = 5.453 (3) Å

  • c = 20.661 (5) Å

  • [beta] = 118.568 (3)°

  • V = 3009.4 (19) Å3

  • Z = 8

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 295 K

  • 0.30 × 0.20 × 0.20 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996[Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.]) Tmin = 0.954, Tmax = 0.991

  • 13379 measured reflections

  • 2802 independent reflections

  • 1955 reflections with I > 2[sigma](I)

  • Rint = 0.031

Refinement
  • R[F2 > 2[sigma](F2)] = 0.045

  • wR(F2) = 0.142

  • S = 1.03

  • 2802 reflections

  • 201 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.24 e Å-3

  • [Delta][rho]min = -0.14 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11-C16 ring.

D-H...A D-H H...A D...A D-H...A
C18-H18A...Cgi 0.96 2.87 3.755 (4) 154
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2004[Bruker (2004). APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: APEX2 and SAINT (Bruker, 2004[Bruker (2004). APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT and XPREP (Bruker, 2004[Bruker (2004). APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); program(s) used to solve structure: SIR92 (Altomare et al., 1994[Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and CAMERON (Watkin et al., 1993[Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.]); software used to prepare material for publication: PARST (Nardelli, 1995[Nardelli, M. (1995). J. Appl. Cryst. 28, 659.]) and WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: HG5275 ).


Acknowledgements

The authors thank Dr Babu Varghese, Scientific Officer, Sophisticated Analytical Instrument Facility (SAIF), Indian Institute of Technology (IIT), Chennai, India, for the data collection. SS and CRG also thank the Rashtriya Sikshana Samithi Trust (RSST) and the Principal, Sri Shivananda Memorial Rashtriya Vidyalaya (SSMRV) Degree College, Bangalore, for their constant support and encouragement in carrying out this work.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.
Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435.  [CrossRef] [details]
Bruker (2004). APEX2, XPREP and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.  [CrossRef] [ChemPort] [ISI]
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Jasinski, J. P., Pek, A. E., Narayana, B., Yathirajan, H. S. & Nayak, P. S. (2010). Acta Cryst. E66, o2546-o2547.  [CSD] [CrossRef] [details]
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.  [CrossRef] [details]
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.


Acta Cryst (2013). E69, o241  [ doi:10.1107/S1600536813000925 ]

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