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Volume 69 
Part 3 
Page o352  
March 2013  

Received 18 January 2013
Accepted 28 January 2013
Online 6 February 2013

Key indicators
Single-crystal X-ray study
T = 173 K
Mean [sigma](C-C) = 0.003 Å
Disorder in main residue
R = 0.055
wR = 0.166
Data-to-parameter ratio = 14.1
Details
Open access

Ethyl 6-(6-methoxynaphthalen-2-yl)-4-(naphthalen-2-yl)-2-oxocyclohex-3-ene-1-carboxylate

aDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India,bDepartment of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA, and cSeQuent Scientific Limited, Biakampady, Mangalore 575 011, India
Correspondence e-mail: jjasinski@keene.edu

The title compound, C30H26O4, contains an oxo-cyclohexane ring in a distorted half-chair configuration, with disorder of two C atoms in a 0.859 (4):0.141 (4) ratio. The dihedral angle between the mean planes of the two napthalene ring systems is 58.6 (8)°.

Related literature

For the biological activity of chalcones, see: Dimmock et al. (1999[Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1150.]); Mayekar et al. (2010[Mayekar, A. N., Li, H., Yathirajan, H. S., Narayana, B. & Suchetha Kumari, N. (2010). Int. J. Chem. (Can.), 2, 114-123.]). For their synthesis, see: Dhar (1981[Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds, pp. 64-70. New York: Wiley-Interscience.]). For related structures, see: Harrison et al. (2010[Harrison, W. T. A., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Sarojini, B. K. (2010). Acta Cryst. E66, o2478.]); Li et al. (2009[Li, H., Mayekar, A. N., Narayana, B., Yathirajan, H. S. & Harrison, W. T. A. (2009). Acta Cryst. E65, o1186.]); Kaur et al. (2012)[Kaur, M., Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Mayekar, A. N. & Narayana, B. (2012). Crystals, 2, 1239-1247.]. For standard bond lengths, 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.]).

[Scheme 1]

Experimental

Crystal data
  • C30H26O4

  • Mr = 450.51

  • Monoclinic, P 21 /c

  • a = 18.4688 (10) Å

  • b = 11.2940 (6) Å

  • c = 10.9676 (5) Å

  • [beta] = 96.082 (5)°

  • V = 2274.8 (2) Å3

  • Z = 4

  • Cu K[alpha] radiation

  • [mu] = 0.69 mm-1

  • T = 173 K

  • 0.24 × 0.18 × 0.06 mm

Data collection
  • Agilent Xcalibur (Eos, Gemini) diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO and CrysAlis RED; Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]) Tmin = 0.864, Tmax = 1.000

  • 14336 measured reflections

  • 4461 independent reflections

  • 3497 reflections with I > 2[sigma](I)

  • Rint = 0.037

Refinement
  • R[F2 > 2[sigma](F2)] = 0.055

  • wR(F2) = 0.166

  • S = 1.09

  • 4461 reflections

  • 317 parameters

  • H-atom parameters constrained

  • [Delta][rho]max = 0.30 e Å-3

  • [Delta][rho]min = -0.22 e Å-3

Data collection: CrysAlis PRO (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012[Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.]); 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: FJ2612 ).


Acknowledgements

MK thanks University of Mysore for research facilities. JPJ acknowledges the NSF-MRI program (grant No. CHE-1039027) for funds to purchase the X-ray diffractometer.

References

Agilent (2012). CrysAlis PRO and CrysAlis RED Agilent Technologies, Yarnton, England.
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.
Dhar, D. N. (1981). The Chemistry of Chalcones and Related Compounds, pp. 64-70. New York: Wiley-Interscience.
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125-1150.  [ISI] [PubMed] [ChemPort]
Harrison, W. T. A., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Sarojini, B. K. (2010). Acta Cryst. E66, o2478.  [CSD] [CrossRef] [details]
Kaur, M., Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Mayekar, A. N. & Narayana, B. (2012). Crystals, 2, 1239-1247.  [CrossRef] [ChemPort]
Li, H., Mayekar, A. N., Narayana, B., Yathirajan, H. S. & Harrison, W. T. A. (2009). Acta Cryst. E65, o1186.  [CSD] [CrossRef] [details]
Mayekar, A. N., Li, H., Yathirajan, H. S., Narayana, B. & Suchetha Kumari, N. (2010). Int. J. Chem. (Can.), 2, 114-123.  [ChemPort]
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.  [CrossRef] [details]


Acta Cryst (2013). E69, o352  [ doi:10.1107/S1600536813002857 ]

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