title: Alkyl levulinates as `green chemistry' precursors: butane-1,4-diyl bis(4-oxopentanoate) and hexane-1,6-diyl bis(4-oxopentanoate).
abstract: Levulinic acid derivatives are potential `green chemistry' renewably sourced molecules with utility in industrial coatings applications. Suitable single crystals of the centrosymmetric title compounds, C14H22O6 and C16H26O6, respectively, were obtained with difficulty. The data for the latter hexane-1,6-diyl compound were extracted from the major fragment of a three-component twinned crystal. Both compounds crystallize in similar-sized unit cells with identical symmetry, utilizing the same weak nonconventional attractive C-H···O(ketone) hydrogen bonds via C(4) and C(5) motifs, which expand to R(2)(2)(30) ring and C(2)(2)(14) chain motifs. Their different packing orientations in similar-sized unit cells suggest that crystal growth involving packing mixes could lead to intergrowths or twins.
authors.affiliation: Carbohydrate Chemistry Group, Callaghan Innovation Research Limited, PO Box 31-310, Lower Hutt, New Zealand. graeme.gainsford@callaghaninnovation.govt.nz
authors.forename: Graeme J
authors.initials: GJ
authors.lastname: Gainsford
authors.forename: Simon
authors.initials: S
authors.lastname: Hinkley
mesh_terms: D002073:Butanes / Q000737:chemistry; D018360:Crystallography, X-Ray; D055772:Green Chemistry Technology; D007982:Levulinic Acids / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010421:Pentanoic Acids / Q000737:chemistry
chemical_list: C430524:3-oxopentanoate; D002073:Butanes; D007982:Levulinic Acids; D010421:Pentanoic Acids; C046888:butane; C032246:levulinic acid