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The asymmetric unit of the title compound, C20H22O10Cl2, consists of a 6-{[(benzyloxy)carbonyl]oxy}group and two chloroacetate groups bonded to a 2-methylhexahydropyrano[3,2-d][1,3]dioxin group at the carbon 1,2 and 3 positions, respectively, of a pyrano ring fused to a dioxin ring. The dihedral angle between the mean planes of the dioxin and benzyl rings is 42.2 (2)°. An extensive array of weak intermolecular C—H...O hydrogen bonds links the molecules into chains along [011]. Additional weak intermolecular C—H...π interactions occur between C—H atoms of the dioxin and benzyl rings and a nearby benzene ring. A MOPAC geometry optimization calculation in vacuo revealed that the dihedral angle between the mean planes of the dioxin and benzyl rings increased by 24.42 to 66.64°, suggesting that the weak intermolecular hydrogen-bonding interactions, in coordination with weak C—H...π interactions, influence the geometry of the resultant crystalline species and help to stabilize the crystal packing.