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

Shalini, S.; Girija, C.R.; Simon, L.; Srinivasan, K.K.; Venkatesha, T.V.; Jotani, M.M.

doi:10.1107/S1600536813000925

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 (C-C) = 0.003 Å
R = 0.045
wR = 0.142
Data-to-parameter ratio = 13.9
Details

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

S. Shalini,^a C. R. Girija,^a ^* Lalitha Simon,^c K. K. Srinivasan,^c T. V. Venkatesha ^d and M. M. Jotani ^e

^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). For bond-length data see: Allen et al. (1987). For ring conformations, see: Cremer & Pople (1975)

Experimental

Crystal data

C₁₈H₁₈O₄
M_r = 298.33
Monoclinic, C 2/c
a = 30.414 (4) Å
b = 5.453 (3) Å
c = 20.661 (5) Å
= 118.568 (3)°
V = 3009.4 (19) Å³
Z = 8
Mo K radiation
= 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) T_min = 0.954, T_max = 0.991
13379 measured reflections
2802 independent reflections
1955 reflections with I > 2(I)
R_int = 0.031

Refinement

R[F² > 2(F²)] = 0.045
wR(F²) = 0.142
S = 1.03
2802 reflections
201 parameters
H-atom parameters constrained
_max = 0.24 e Å^-3
_min = -0.14 e Å^-3

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C11-C16 ring.

D-HA	D-H	HA	DA	D-HA
C18-H18ACgⁱ	0.96	2.87	3.755 (4)	154
Symmetry code: (i) x, y-1, z.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012) and CAMERON (Watkin et al., 1993); software used to prepare material for publication: PARST (Nardelli, 1995) and WinGX (Farrugia, 2012).

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.
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.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.
Jasinski, J. P., Pek, A. E., Narayana, B., Yathirajan, H. S. & Nayak, P. S. (2010). Acta Cryst. E66, o2546-o2547.
Nardelli, M. (1995). J. Appl. Cryst. 28, 659.
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.
Watkin, D. M., Pearce, L. & Prout, C. K. (1993). CAMERON. Chemical Crystallography Laboratory, University of Oxford, England.

organic compounds