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Crystals 2011, 1(4), 229-235; doi:10.3390/cryst1040229

The Crystal and Molecular Structure of (2Z)-2-[3-(4-Methoxybenzoyl)-4,4-dimethyl-1,2-oxazolidin-2-ylidene]-1-(4-methoxyphenyl)ethanone

1
Department of Chemistry & Biology, Ryerson University, 350 Victoria Street, Toronto ON M5B 2K3, Canada
2
Department of Chemistry, Acadia University, Wolfville NS B4P 2R6, Canada
3
Department of Chemistry, University of Toronto, 80 St. George Street, Toronto ON M5S 3H6, Canada
Queries concerning specific aspects of the crystal structure determination should be directed to this author.
*
Author to whom correspondence should be addressed.
Received: 14 September 2011 / Revised: 20 October 2011 / Accepted: 28 October 2011 / Published: 31 October 2011
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Abstract

The crystal and molecular structure of the title compound, viz., (2Z)-2-[3-(4-methoxybenzoyl)-4,4-dimethyl-1,2,-oxazolidin-2-ylidene]-1-(4-methoxyphenyl)ethanone (4), is reported. Compound 4 crystallises from toluene/hexanes mixtures in the P21/c space group with eight molecules in the unit cell. The unit cell parameters are: a = 20.9410(11) Å, b = 8.7523(5) Å, c = 21.2291(9) Å; β = 93.529(3)° and V = 3883.5(3) Å3. There are two structurally distinct molecules of 4 found in the solid-state which differ primarily in terms of the observed torsion angles and the overall intramolecular spacing between the aromatic groups. Bond lengths and angles of this tertiary amide are otherwise typical. This is the first crystallographically characterised example of this class of oxazoline precursors, which have previously found application in the syntheses of other heterocycles. Density functional theory (b3lyp 6-311++G** level of sophistication) has likewise been applied to estimate the gas-phase structure of the title compound.
Keywords: oxazoline; X-ray crystal structure; tertiary amide; ketone; azole; oxazole; DFT oxazoline; X-ray crystal structure; tertiary amide; ketone; azole; oxazole; DFT
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MDPI and ACS Style

Petrov, A.; Jones, R.C.; Vaughan, D.G.; Lough, A.J.; Gossage, R.A. The Crystal and Molecular Structure of (2Z)-2-[3-(4-Methoxybenzoyl)-4,4-dimethyl-1,2-oxazolidin-2-ylidene]-1-(4-methoxyphenyl)ethanone. Crystals 2011, 1, 229-235.

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