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Volume 69 
Part 3 
Page o442  
March 2013  

Received 22 December 2012
Accepted 3 January 2013
Online 23 February 2013

Key indicators
Single-crystal X-ray study
T = 293 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.045
wR = 0.143
Data-to-parameter ratio = 15.8
Details
Open access

(3E)-11,16-Dioxatricyclo[15.4.0.05,10]henicosa-1(21),3,5,7,9,17,19-heptaen-2-one

aDepartment of Physics, SMK Fomra Institute of Technology, Thaiyur, Chennai 603 103, India,bDepartment of Organic Chemistry, University of Madras, Guindy Campus, Chennai 600 025, India, and cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
Correspondence e-mail: a_sp59@yahoo.in

The title compound, C19H18O3, crystallizes with three molecules (A, B and C) in the asymmetric unit. The carbonyl O atom shows positional disorder over two sites in molecules A and B; the site-occupancy ratios are 0.76 (3):0.24 (3) and 0.86 (3):0.14 (3), respectively. The ethylene fragments in each molecule have an E conformation, while the C-O-C-C torsion angles indicate near planarity. The dihedral angles formed by the aromatic rings are 20.0 (1), 23.7 (1) and 16.1 (1)° for molecules A, B and C, respectively. Intramolecular C-H...O hydrogen bonds occur in each molecule.

Related literature

For the biological activities of chalcones, see: Xue et al. (2004[Xue, C. X., Cui, S. Y., Liu, M. C., Hu, Z. D. & Fan, B. T. (2004). Eur. J. Med. Chem. 39, 745-753.]); Lee et al. (2006[Lee, Y. S., Lim, S. S., Shin, K. H., Kim, Y. S., Ohuchi, K. & Jung, S. H. (2006). Biol. Pharm. Bull. 29, 1028-1031.]); Bhat et al. (2005[Bhat, B. A., Dhar, K. L., Puri, S. C., Saxena, A. K., Shanmugavel, M. & Qazi, G. N. (2005). Bioorg. Med. Chem. Lett. 15, 3177-3180.]); Satyanarayana et al. (2004[Satyanarayana, M., Tiwari, P., Tripathi, B. K., Srivastava, A. K. & Pratap, R. (2004). Bioorg. Med. Chem. Lett. 12, 883-889.]). For a related crown ether structure, see: Anh et al. (2011[Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Soldatova, S. A. & Khrustalev, V. N. (2011). Acta Cryst. E67, o1128-o1129.]).

[Scheme 1]

Experimental

Crystal data
  • C19H18O3

  • Mr = 294.34

  • Triclinic, [P \overline 1]

  • a = 9.0976 (6) Å

  • b = 16.9797 (11) Å

  • c = 17.2713 (9) Å

  • [alpha] = 62.590 (2)°

  • [beta] = 88.440 (2)°

  • [gamma] = 78.092 (2)°

  • V = 2310.4 (2) Å3

  • Z = 6

  • Mo K[alpha] radiation

  • [mu] = 0.09 mm-1

  • T = 293 K

  • 0.40 × 0.30 × 0.25 mm

Data collection
  • Bruker APEXII CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2008[Bruker. (2008). APEX2 and SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.967, Tmax = 0.979

  • 44770 measured reflections

  • 9919 independent reflections

  • 5862 reflections with I > 2[sigma](I)

  • Rint = 0.032

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

  • wR(F2) = 0.143

  • S = 1.04

  • 9919 reflections

  • 629 parameters

  • 15 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • [Delta][rho]max = 0.19 e Å-3

  • [Delta][rho]min = -0.16 e Å-3

Table 1
Hydrogen-bond geometry (Å, °)

D-H...A D-H H...A D...A D-H...A
C18-H18...O2 0.93 2.15 2.746 (2) 121
C18-H18...O3 0.93 2.12 2.763 (2) 126
C38-H38...O5 0.93 2.24 2.753 (2) 114
C38-H38...O6 0.93 2.13 2.753 (3) 123
C56-H56...O8 0.93 2.23 2.766 (2) 116
C56-H56...O9 0.93 2.15 2.764 (2) 122

Data collection: APEX2 (Bruker, 2008[Bruker. (2008). APEX2 and SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2008[Bruker. (2008). APEX2 and 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: ORTEP-3 (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).


Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BX2434 ).


Acknowledgements

The authors thank Dr Babu Varghese and SAIF, IIT, Chennai, India, for the data collection.

References

Anh, L. T., Hieu, T. H., Soldatenkov, A. T., Soldatova, S. A. & Khrustalev, V. N. (2011). Acta Cryst. E67, o1128-o1129.  [CSD] [CrossRef] [details]
Bhat, B. A., Dhar, K. L., Puri, S. C., Saxena, A. K., Shanmugavel, M. & Qazi, G. N. (2005). Bioorg. Med. Chem. Lett. 15, 3177-3180.  [CrossRef] [PubMed] [ChemPort]
Bruker. (2008). APEX2 and SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.  [ISI] [CrossRef] [ChemPort] [details]
Lee, Y. S., Lim, S. S., Shin, K. H., Kim, Y. S., Ohuchi, K. & Jung, S. H. (2006). Biol. Pharm. Bull. 29, 1028-1031.  [CrossRef] [PubMed] [ChemPort]
Satyanarayana, M., Tiwari, P., Tripathi, B. K., Srivastava, A. K. & Pratap, R. (2004). Bioorg. Med. Chem. Lett. 12, 883-889.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]
Spek, A. L. (2009). Acta Cryst. D65, 148-155.  [ISI] [CrossRef] [details]
Xue, C. X., Cui, S. Y., Liu, M. C., Hu, Z. D. & Fan, B. T. (2004). Eur. J. Med. Chem. 39, 745-753.  [ISI] [CrossRef] [PubMed] [ChemPort]


Acta Cryst (2013). E69, o442  [ doi:10.1107/S1600536813000299 ]

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