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

Kaur, M.; Jasinski, J.P.; Keeley, A.C.; Yathirajan, H.S.; Mayekar, A.N.

doi:10.1107/S1600536813002857

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 (C-C) = 0.003 Å
Disorder in main residue
R = 0.055
wR = 0.166
Data-to-parameter ratio = 14.1
Details

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

Manpreet Kaur,^a Jerry P. Jasinski,^b ^* Amanda C. Keeley,^b H. S. Yathirajan ^a and Anil N. Mayekar ^c

^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); Mayekar et al. (2010). For their synthesis, see: Dhar (1981). For related structures, see: Harrison et al. (2010); Li et al. (2009); Kaur et al. (2012). For standard bond lengths, see Allen et al. (1987).

Experimental

Crystal data

C₃₀H₂₆O₄
M_r = 450.51
Monoclinic, P 2₁ /c
a = 18.4688 (10) Å
b = 11.2940 (6) Å
c = 10.9676 (5) Å
= 96.082 (5)°
V = 2274.8 (2) Å³
Z = 4
Cu K radiation
= 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) T_min = 0.864, T_max = 1.000
14336 measured reflections
4461 independent reflections
3497 reflections with I > 2(I)
R_int = 0.037

Refinement

R[F² > 2(F²)] = 0.055
wR(F²) = 0.166
S = 1.09
4461 reflections
317 parameters
H-atom parameters constrained
_max = 0.30 e Å^-3
_min = -0.22 e Å^-3

Data collection: CrysAlis PRO (Agilent, 2012); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); 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.
Harrison, W. T. A., Mayekar, A. N., Yathirajan, H. S., Narayana, B. & Sarojini, B. K. (2010). Acta Cryst. E66, o2478.
Kaur, M., Jasinski, J. P., Butcher, R. J., Yathirajan, H. S., Mayekar, A. N. & Narayana, B. (2012). Crystals, 2, 1239-1247.
Li, H., Mayekar, A. N., Narayana, B., Yathirajan, H. S. & Harrison, W. T. A. (2009). Acta Cryst. E65, o1186.
Mayekar, A. N., Li, H., Yathirajan, H. S., Narayana, B. & Suchetha Kumari, N. (2010). Int. J. Chem. (Can.), 2, 114-123.
Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.

organic compounds